data_global
 
# PROCESSING SUMMARY (IUCr Office Use Only)
 
_journal_data_validation_number      ?
 
_journal_date_recd_electronic      2020-03-09
_journal_date_to_coeditor            ?
_journal_date_from_coeditor          ?
_journal_date_accepted     2020-05-21
_journal_date_printers_first         ?
_journal_date_printers_final         ?
_journal_date_proofs_out             ?
_journal_date_proofs_in              ?
_journal_coeditor_name               ?
_journal_coeditor_code      BM5125SUP1
_journal_coeditor_notes
; ?
;
_journal_techeditor_code      B200687
_iucr_compatibility_tag          ACTA95
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM                  ?
_journal_name_full                   ?
_journal_year                        ?
_journal_volume                      ?
_journal_issue                       ?
_journal_page_first                  ?
_journal_page_last                   ?
_journal_paper_category      FA
_journal_suppl_publ_number           ?
_journal_suppl_publ_pages            ?
 
#==============================================================================
#
# SUBMISSION DETAILS
# Name and address of author for correspondence
 
_publ_contact_author_name       'Angshuman Roy Choudhury'
_publ_contact_author_address     
;
Deapartment of Chemical Sciencces, Indian INstitute of
Sccience Education and Research, Mohali, Sector 81,
S. A. S. Nagar, Manauli PO, Mohali, Punjab. 140306.
India 
;
_publ_contact_author_email       'angshurc@iisermohali.ac.in '
_publ_contact_author_fax         ?
_publ_contact_author_phone       00911722293167
 
 # TITLE AND AUTHOR LIST
 
_publ_section_title
; 'Evaluation of fluorine mediated intermolecular interactions in 
tetrafluorinated tetrahydroisoquinoline derivatives: 
Synthesis and Computational Studies'
;
_publ_section_title_footnote
; ?
;
 
data_6-1
_database_code_depnum_ccdc_archive 'CCDC 1540717'
 
_audit_creation_date                    2020-03-09T08:58:51-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
_chemical_absolute_configuration        unk
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21 1'
_symmetry_space_group_name_Hall         'P 2yb'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 x,y,z
 2 -x,y+1/2,-z

_symmetry_Int_Tables_number        4
_cell_length_a                          8.210(4)
_cell_length_b                          6.330(2)
_cell_length_c                          17.277(9)
_cell_angle_alpha                       90
_cell_angle_beta                        102.410(19)
_cell_angle_gamma                       90
_cell_volume                            876.9(7)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           2611
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.25
_exptl_crystal_size_mid                 0.22
_exptl_crystal_size_min                 0.18
_exptl_crystal_density_diffrn           1.467
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    400
_exptl_absorpt_coefficient_mu           0.119
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.798
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   9368
_diffrn_reflns_av_R_equivalents         0.0433
_diffrn_reflns_theta_min                3.038
_diffrn_reflns_theta_max                27.505
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.995
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.995
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.992
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -8
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min              -22
_diffrn_reflns_limit_l_max              22
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4001
_reflns_number_gt                       3361
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0601
_refine_ls_R_factor_gt                  0.0514
_refine_ls_wR_factor_ref                0.1441
_refine_ls_goodness_of_fit_ref          1.127
_refine_ls_restrained_S_all             1.126
_refine_ls_number_reflns                4001
_refine_ls_number_parameters            254
_refine_ls_number_restraints            1
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0779P)²+0.0363P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.404
_refine_diff_density_min                -0.274
_refine_diff_density_rms                0.061
_refine_ls_extinction_method            none
_refine_ls_abs_structure_details
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          -0.2(5)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C1 C 0.6381(4) 0.5050(5) 0.29011(18) 0.0251(7) Uani 1 1 d . . . . .
 H1 H 0.616886 0.659849 0.281996 0.030 Uiso 1 1 calc R . . . .
 C2 C 0.4796(5) 0.1709(6) 0.2782(2) 0.0291(7) Uani 1 1 d . . . . .
 H2A H 0.577736 0.095787 0.266968 0.035 Uiso 1 1 calc R . . . .
 H2B H 0.377717 0.100580 0.248253 0.035 Uiso 1 1 calc R . . . .
 C3 C 0.4830(5) 0.1615(6) 0.3664(2) 0.0315(8) Uani 1 1 d . . . . .
 H3A H 0.373459 0.207674 0.375612 0.038 Uiso 1 1 calc R . . . .
 H3B H 0.501121 0.013589 0.384836 0.038 Uiso 1 1 calc R . . . .
 C4 C 0.6728(4) 0.2602(6) 0.4950(2) 0.0274(7) Uani 1 1 d . . . . .
 H4 H 0.626841 0.146160 0.518959 0.033 Uiso 1 1 calc R . . . .
 C5 C 0.7940(4) 0.3866(5) 0.54080(19) 0.0269(7) Uani 1 1 d . . . . .
 C6 C 0.8588(4) 0.5567(6) 0.5057(2) 0.0281(7) Uani 1 1 d . . . . .
 H6 H 0.938945 0.647467 0.537012 0.034 Uiso 1 1 calc R . . . .
 C7 C 0.8065(4) 0.5931(6) 0.42527(19) 0.0278(7) Uani 1 1 d . . . . .
 H7 H 0.853343 0.706648 0.401430 0.033 Uiso 1 1 calc R . . . .
 C8 C 0.6850(4) 0.4646(5) 0.37855(19) 0.0258(7) Uani 1 1 d . . . . .
 C9 C 0.6171(4) 0.2981(5) 0.41393(19) 0.0256(7) Uani 1 1 d . . . . .
 C10 C 0.8046(5) 0.1700(7) 0.6541(2) 0.0349(8) Uani 1 1 d . . . . .
 H10A H 0.832916 0.045521 0.625986 0.052 Uiso 1 1 calc GR . . . .
 H10B H 0.683666 0.174992 0.649884 0.052 Uiso 1 1 calc GR . . . .
 H10C H 0.861141 0.161613 0.710104 0.052 Uiso 1 1 calc GR . . . .
 C11 C 0.4299(4) 0.4212(5) 0.17016(19) 0.0252(7) Uani 1 1 d . . . . .
 C12 C 0.3594(4) 0.6155(5) 0.1423(2) 0.0283(7) Uani 1 1 d . . . . .
 C13 C 0.2976(5) 0.6503(6) 0.0625(2) 0.0297(7) Uani 1 1 d . . . . .
 C14 C 0.3012(4) 0.4965(6) 0.0073(2) 0.0295(7) Uani 1 1 d . . . . .
 H14 H 0.256943 0.521479 -0.047427 0.035 Uiso 1 1 calc R . . . .
 C15 C 0.3714(4) 0.3026(6) 0.0336(2) 0.0308(8) Uani 1 1 d . . . . .
 H15 H 0.375070 0.193162 -0.003615 0.037 Uiso 1 1 calc R . . . .
 C16 C 0.4359(4) 0.2670(6) 0.1131(2) 0.0282(7) Uani 1 1 d . . . . .
 H16 H 0.485572 0.134269 0.129399 0.034 Uiso 1 1 calc R . . . .
 C17 C 0.7798(4) 0.4443(5) 0.24867(19) 0.0266(7) Uani 1 1 d . . . . .
 C18 C 0.8109(4) 0.5654(6) 0.18685(19) 0.0272(7) Uani 1 1 d . . . . .
 C19 C 0.9231(4) 0.5066(6) 0.14236(19) 0.0312(8) Uani 1 1 d . . . . .
 C20 C 1.0120(4) 0.3205(6) 0.1581(2) 0.0339(8) Uani 1 1 d . . . . .
 H20 H 1.088238 0.277832 0.126840 0.041 Uiso 1 1 calc R . . . .
 C21 C 0.9865(4) 0.1975(6) 0.2213(2) 0.0333(8) Uani 1 1 d . . . . .
 H21 H 1.046322 0.069021 0.233604 0.040 Uiso 1 1 calc R . . . .
 C22 C 0.8739(4) 0.2615(6) 0.2666(2) 0.0291(7) Uani 1 1 d . . . . .
 H22 H 0.861127 0.178257 0.310640 0.035 Uiso 1 1 calc R . . . .
 N1 N 0.4819(3) 0.3913(4) 0.25347(16) 0.0256(6) Uani 1 1 d . . . . .
 O1 O 0.8574(3) 0.3576(4) 0.61959(13) 0.0306(6) Uani 1 1 d . . . . .
 F1 F 0.7279(3) 0.7510(3) 0.16848(12) 0.0343(5) Uani 1 1 d . . . . .
 F2 F 0.9480(3) 0.6344(4) 0.08376(13) 0.0399(6) Uani 1 1 d . . . . .
 F3 F 0.3469(3) 0.7710(4) 0.19399(12) 0.0377(5) Uani 1 1 d . . . . .
 F4 F 0.2298(3) 0.8411(3) 0.04026(13) 0.0393(5) Uani 1 1 d . . . . .

 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C1 H1 . 1 ?
C1 C8 . 1.515(4) ?
C1 C17 . 1.540(5) ?
C1 N1 . 1.488(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.519(5) ?
C2 N1 . 1.461(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.498(5) ?
C4 H4 . 0.95 ?
C4 C5 . 1.386(5) ?
C4 C9 . 1.397(4) ?
C5 C6 . 1.396(5) ?
C5 O1 . 1.361(4) ?
C6 H6 . 0.95 ?
C6 C7 . 1.382(5) ?
C7 H7 . 0.95 ?
C7 C8 . 1.401(5) ?
C8 C9 . 1.393(5) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.437(5) ?
C11 C12 . 1.400(5) ?
C11 C16 . 1.396(5) ?
C11 N1 . 1.423(4) ?
C12 C13 . 1.380(5) ?
C12 F3 . 1.348(4) ?
C13 C14 . 1.368(5) ?
C13 F4 . 1.350(4) ?
C14 H14 . 0.95 ?
C14 C15 . 1.391(5) ?
C15 H15 . 0.95 ?
C15 C16 . 1.380(5) ?
C16 H16 . 0.95 ?
C17 C18 . 1.382(5) ?
C17 C22 . 1.389(5) ?
C18 C19 . 1.372(5) ?
C18 F1 . 1.361(4) ?
C19 C20 . 1.381(6) ?
C19 F2 . 1.346(4) ?
C20 H20 . 0.95 ?
C20 C21 . 1.393(5) ?
C21 H21 . 0.95 ?
C21 C22 . 1.394(5) ?
C22 H22 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C8 C1 H1 107.8 . . ?
C8 C1 C17 111.9(3) . . ?
C17 C1 H1 107.8 . . ?
N1 C1 H1 107.8 . . ?
N1 C1 C8 110.9(3) . . ?
N1 C1 C17 110.5(3) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.4(3) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C9 C3 C2 112.3(3) . . ?
C9 C3 H3A 109.1 . . ?
C9 C3 H3B 109.1 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C9 120.9(3) . . ?
C9 C4 H4 119.5 . . ?
C4 C5 C6 119.4(3) . . ?
O1 C5 C4 124.5(3) . . ?
O1 C5 C6 116.1(3) . . ?
C5 C6 H6 120 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C1 118.6(3) . . ?
C9 C8 C1 122.1(3) . . ?
C9 C8 C7 119.3(3) . . ?
C4 C9 C3 119.6(3) . . ?
C8 C9 C3 120.8(3) . . ?
C8 C9 C4 119.6(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C12 C11 N1 118.5(3) . . ?
C16 C11 C12 116.5(3) . . ?
C16 C11 N1 124.9(3) . . ?
C13 C12 C11 121.3(3) . . ?
F3 C12 C11 119.9(3) . . ?
F3 C12 C13 118.8(3) . . ?
C14 C13 C12 121.7(3) . . ?
F4 C13 C12 117.9(3) . . ?
F4 C13 C14 120.4(3) . . ?
C13 C14 H14 121 . . ?
C13 C14 C15 118.0(3) . . ?
C15 C14 H14 121 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C1 120.3(3) . . ?
C18 C17 C22 116.6(3) . . ?
C22 C17 C1 122.9(3) . . ?
C19 C18 C17 122.7(3) . . ?
F1 C18 C17 119.5(3) . . ?
F1 C18 C19 117.8(3) . . ?
C18 C19 C20 120.7(3) . . ?
F2 C19 C18 119.2(3) . . ?
F2 C19 C20 120.1(3) . . ?
C19 C20 H20 121 . . ?
C19 C20 C21 118.0(3) . . ?
C21 C20 H20 121 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 121.4(3) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C2 N1 C1 113.7(3) . . ?
C11 N1 C1 114.2(3) . . ?
C11 N1 C2 113.8(3) . . ?
C5 O1 C10 116.3(3) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C1 C8 C9 C3 -5.1(5) . . . . ?
C1 C8 C9 C4 175.9(3) . . . . ?
C1 C17 C18 C19 -172.8(3) . . . . ?
C1 C17 C18 F1 7.1(4) . . . . ?
C1 C17 C22 C21 171.7(3) . . . . ?
C2 C3 C9 C4 -160.0(3) . . . . ?
C2 C3 C9 C8 21.1(5) . . . . ?
C3 C2 N1 C1 64.7(4) . . . . ?
C3 C2 N1 C11 -162.3(3) . . . . ?
C4 C5 C6 C7 -2.4(5) . . . . ?
C4 C5 O1 C10 6.4(5) . . . . ?
C5 C4 C9 C3 -178.6(3) . . . . ?
C5 C4 C9 C8 0.4(5) . . . . ?
C5 C6 C7 C8 1.8(5) . . . . ?
C6 C5 O1 C10 -173.5(3) . . . . ?
C6 C7 C8 C1 -177.1(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C3 178.0(3) . . . . ?
C7 C8 C9 C4 -1.0(5) . . . . ?
C8 C1 C17 C18 -142.5(3) . . . . ?
C8 C1 C17 C22 42.2(4) . . . . ?
C8 C1 N1 C2 -47.0(4) . . . . ?
C8 C1 N1 C11 -179.9(3) . . . . ?
C9 C4 C5 C6 1.3(5) . . . . ?
C9 C4 C5 O1 -178.6(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C11 C12 C13 F4 179.3(3) . . . . ?
C12 C11 C16 C15 -1.8(5) . . . . ?
C12 C11 N1 C1 -74.1(4) . . . . ?
C12 C11 N1 C2 153.1(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C11 1.5(5) . . . . ?
C16 C11 C12 C13 0.8(5) . . . . ?
C16 C11 C12 F3 178.9(3) . . . . ?
C16 C11 N1 C1 109.2(4) . . . . ?
C16 C11 N1 C2 -23.6(5) . . . . ?
C17 C1 C8 C7 69.9(4) . . . . ?
C17 C1 C8 C9 -107.1(4) . . . . ?
C17 C1 N1 C2 77.6(3) . . . . ?
C17 C1 N1 C11 -55.2(4) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C17 C18 C19 F2 -179.2(3) . . . . ?
C18 C17 C22 C21 -3.8(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 C22 0.2(5) . . . . ?
C20 C21 C22 C17 2.3(5) . . . . ?
C22 C17 C18 C19 2.8(5) . . . . ?
C22 C17 C18 F1 -177.3(3) . . . . ?
N1 C1 C8 C7 -166.3(3) . . . . ?
N1 C1 C8 C9 16.8(4) . . . . ?
N1 C1 C17 C18 93.5(4) . . . . ?
N1 C1 C17 C22 -81.9(4) . . . . ?
N1 C2 C3 C9 -49.1(4) . . . . ?
N1 C11 C12 C13 -176.2(3) . . . . ?
N1 C11 C12 F3 2.0(5) . . . . ?
N1 C11 C16 C15 175.0(3) . . . . ?
O1 C5 C6 C7 177.5(3) . . . . ?
F1 C18 C19 C20 179.7(3) . . . . ?
F1 C18 C19 F2 0.9(5) . . . . ?
F2 C19 C20 C21 177.6(3) . . . . ?
F3 C12 C13 C14 -177.7(3) . . . . ?
F3 C12 C13 F4 1.1(5) . . . . ?
F4 C13 C14 C15 -179.6(3) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-2
_database_code_depnum_ccdc_archive 'CCDC 1540721' 
_audit_creation_date                    2020-03-09T08:59:51-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 x,y,z
 2 -x,y+1/2,-z+1/2
 3 -x,-y,-z
 4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number        14
_cell_length_a                          9.705(3)
_cell_length_b                          13.476(3)
_cell_length_c                          13.843(4)
_cell_angle_alpha                       90
_cell_angle_beta                        101.159(11)
_cell_angle_gamma                       90
_cell_volume                            1776.2(8)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4466
_cell_measurement_theta_min             2.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.22
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.18
_exptl_crystal_density_diffrn           1.449
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.117
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.908
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71075
_diffrn_measurement_device_type
;
        Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   11947
_diffrn_reflns_av_R_equivalents         0.0588
_diffrn_reflns_theta_min                2.805
_diffrn_reflns_theta_max                27.498
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.99
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.99
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.99
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -17
_diffrn_reflns_limit_k_max              17
_diffrn_reflns_limit_l_min              -16
_diffrn_reflns_limit_l_max              17
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4037
_reflns_number_gt                       3065
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0667
_refine_ls_R_factor_gt                  0.0487
_refine_ls_wR_factor_ref                0.1347
_refine_ls_goodness_of_fit_ref          1.07
_refine_ls_restrained_S_all             1.07
_refine_ls_number_reflns                4037
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0647P)²+0.4250P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.288
_refine_diff_density_min                -0.241
_refine_diff_density_rms                0.057
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'SIR2004 (Burla et al., 2007)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C1 -0.08483(17) 0.86709(12) 0.33681(12) 0.0190(3) Uani d 1 . . C
H1 0.0063 0.8992 0.367 0.023 Uiso calc 1 . . H
C2 -0.18494(17) 0.70394(12) 0.28595(12) 0.0215(3) Uani d 1 . . C
H2A -0.1634 0.6381 0.2608 0.026 Uiso calc 1 . . H
H2B -0.2502 0.7389 0.233 0.026 Uiso calc 1 . . H
C3 -0.25218(18) 0.69158(12) 0.37575(13) 0.0236(4) Uani d 1 . . C
H3A -0.3476 0.6636 0.3549 0.028 Uiso calc 1 . . H
H3B -0.1961 0.644 0.4219 0.028 Uiso calc 1 . . H
C4 -0.34982(17) 0.79782(13) 0.49695(12) 0.0225(4) Uani d 1 . . C
H4 -0.4059 0.7429 0.5084 0.027 Uiso calc 1 . . H
C5 -0.35645(17) 0.88567(13) 0.54850(12) 0.0222(4) Uani d 1 . . C
C6 -0.27544(18) 0.96715(13) 0.53257(13) 0.0237(4) Uani d 1 . . C
H6 -0.2793 1.0271 0.568 0.028 Uiso calc 1 . . H
C7 -0.18863(17) 0.95902(12) 0.46368(12) 0.0220(3) Uani d 1 . . C
H7 -0.1342 1.0146 0.4515 0.026 Uiso calc 1 . . H
C8 -0.17991(17) 0.87065(12) 0.41198(11) 0.0194(3) Uani d 1 . . C
C9 -0.26194(16) 0.78927(12) 0.42859(12) 0.0198(3) Uani d 1 . . C
C17 -0.14755(17) 0.92530(12) 0.24323(12) 0.0200(3) Uani d 1 . . C
C18 -0.06224(18) 0.97450(12) 0.18894(13) 0.0232(4) Uani d 1 . . C
C19 -0.1120(2) 1.02610(13) 0.10241(14) 0.0284(4) Uani d 1 . . C
H19 -0.0506 1.0602 0.068 0.034 Uiso calc 1 . . H
C20 -0.2550(2) 1.02522(13) 0.06923(13) 0.0295(4) Uani d 1 . . C
C21 -0.3468(2) 0.97771(13) 0.11817(13) 0.0277(4) Uani d 1 . . C
H21 -0.4451 0.9785 0.0931 0.033 Uiso calc 1 . . H
C22 -0.29141(18) 0.92853(13) 0.20552(12) 0.0233(4) Uani d 1 . . C
H22 -0.3536 0.8962 0.2405 0.028 Uiso calc 1 . . H
C11 0.04462(17) 0.75126(12) 0.25222(12) 0.0194(3) Uani d 1 . . C
C12 0.18607(18) 0.76408(12) 0.29222(12) 0.0218(4) Uani d 1 . . C
C13 0.28775(18) 0.75549(13) 0.23544(13) 0.0248(4) Uani d 1 . . C
C14 0.25281(19) 0.73385(13) 0.13594(13) 0.0252(4) Uani d 1 . . C
H14 0.3231 0.7279 0.0971 0.03 Uiso calc 1 . . H
C15 0.11169(19) 0.72117(13) 0.09480(13) 0.0246(4) Uani d 1 . . C
H15 0.0848 0.7068 0.0266 0.03 Uiso calc 1 . . H
C16 0.00940(18) 0.72914(12) 0.15176(12) 0.0229(4) Uani d 1 . . C
H16 -0.0864 0.7194 0.122 0.028 Uiso calc 1 . . H
C10 -0.4520(2) 0.97158(14) 0.67227(14) 0.0301(4) Uani d 1 . . C
H10A -0.4839 1.028 0.629 0.045 Uiso calc 1 . . H
H10B -0.3583 0.9857 0.7109 0.045 Uiso calc 1 . . H
H10C -0.5177 0.9607 0.7168 0.045 Uiso calc 1 . . H
N1 -0.05506(15) 0.76170(10) 0.31508(10) 0.0197(3) Uani d 1 . . N
O1 -0.44620(13) 0.88456(10) 0.61407(9) 0.0283(3) Uani d 1 . . O
F3 0.07894(11) 0.97360(8) 0.22225(8) 0.0300(3) Uani d 1 . . F
F4 -0.30735(14) 1.07384(10) -0.01634(9) 0.0447(3) Uani d 1 . . F
F1 0.22781(11) 0.78603(8) 0.38935(7) 0.0294(3) Uani d 1 . . F
F2 0.42376(11) 0.76888(9) 0.27916(8) 0.0367(3) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C1 H1 . 1 ?
C1 C8 . 1.519(2) ?
C1 C17 . 1.536(2) ?
C1 N1 . 1.491(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.521(2) ?
C2 N1 . 1.470(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.518(2) ?
C4 H4 . 0.95 ?
C4 C5 . 1.390(2) ?
C4 C9 . 1.396(2) ?
C5 C6 . 1.393(2) ?
C5 O1 . 1.3744(19) ?
C6 H6 . 0.95 ?
C6 C7 . 1.394(2) ?
C7 H7 . 0.95 ?
C7 C8 . 1.400(2) ?
C8 C9 . 1.400(2) ?
C17 C18 . 1.389(2) ?
C17 C22 . 1.393(2) ?
C18 C19 . 1.388(3) ?
C18 F3 . 1.358(2) ?
C19 H19 . 0.95 ?
C19 C20 . 1.376(3) ?
C20 C21 . 1.377(3) ?
C20 F4 . 1.363(2) ?
C21 H21 . 0.95 ?
C21 C22 . 1.392(2) ?
C22 H22 . 0.95 ?
C11 C12 . 1.388(2) ?
C11 C16 . 1.398(2) ?
C11 N1 . 1.428(2) ?
C12 C13 . 1.380(2) ?
C12 F1 . 1.3596(19) ?
C13 C14 . 1.384(3) ?
C13 F2 . 1.354(2) ?
C14 H14 . 0.95 ?
C14 C15 . 1.388(3) ?
C15 H15 . 0.95 ?
C15 C16 . 1.386(2) ?
C16 H16 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.430(2) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C8 C1 H1 107.8 . . ?
C8 C1 C17 111.56(13) . . ?
C17 C1 H1 107.8 . . ?
N1 C1 H1 107.8 . . ?
N1 C1 C8 109.59(12) . . ?
N1 C1 C17 112.14(13) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110 . . ?
C3 C2 H2B 110 . . ?
N1 C2 H2A 110 . . ?
N1 C2 H2B 110 . . ?
N1 C2 C3 108.33(13) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C9 C3 C2 112.06(13) . . ?
C9 C3 H3A 109.2 . . ?
C9 C3 H3B 109.2 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C9 120.89(15) . . ?
C9 C4 H4 119.6 . . ?
C4 C5 C6 120.43(15) . . ?
O1 C5 C4 115.34(15) . . ?
O1 C5 C6 124.23(15) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.74(15) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.39(15) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C1 118.80(14) . . ?
C9 C8 C1 121.85(14) . . ?
C9 C8 C7 119.32(14) . . ?
C4 C9 C3 120.11(15) . . ?
C4 C9 C8 119.21(15) . . ?
C8 C9 C3 120.65(14) . . ?
C18 C17 C1 121.30(15) . . ?
C18 C17 C22 116.19(15) . . ?
C22 C17 C1 122.46(14) . . ?
C19 C18 C17 124.16(17) . . ?
F3 C18 C17 118.66(15) . . ?
F3 C18 C19 117.17(15) . . ?
C18 C19 H19 121.8 . . ?
C20 C19 C18 116.34(16) . . ?
C20 C19 H19 121.8 . . ?
C19 C20 C21 123.15(16) . . ?
F4 C20 C19 117.92(16) . . ?
F4 C20 C21 118.93(17) . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.10(17) . . ?
C22 C21 H21 120.9 . . ?
C17 C22 H22 119 . . ?
C21 C22 C17 122.04(16) . . ?
C21 C22 H22 119 . . ?
C12 C11 C16 117.11(15) . . ?
C12 C11 N1 118.62(15) . . ?
C16 C11 N1 124.27(15) . . ?
C13 C12 C11 121.55(15) . . ?
F1 C12 C11 120.27(14) . . ?
F1 C12 C13 118.19(15) . . ?
C12 C13 C14 121.32(16) . . ?
F2 C13 C12 118.49(15) . . ?
F2 C13 C14 120.19(15) . . ?
C13 C14 H14 121.1 . . ?
C13 C14 C15 117.79(15) . . ?
C15 C14 H14 121.1 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.02(16) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.20(16) . . ?
C15 C16 H16 119.4 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C2 N1 C1 111.73(13) . . ?
C11 N1 C1 113.41(12) . . ?
C11 N1 C2 115.26(13) . . ?
C5 O1 C10 117.53(14) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C1 C8 C9 C3 3.6(2) . . . . ?
C1 C8 C9 C4 -178.47(15) . . . . ?
C1 C17 C18 C19 178.19(16) . . . . ?
C1 C17 C18 F3 -2.5(2) . . . . ?
C1 C17 C22 C21 -176.98(15) . . . . ?
C2 C3 C9 C4 164.28(15) . . . . ?
C2 C3 C9 C8 -17.8(2) . . . . ?
C3 C2 N1 C1 -69.58(16) . . . . ?
C3 C2 N1 C11 159.04(13) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C4 C5 O1 C10 177.17(15) . . . . ?
C5 C4 C9 C3 177.78(15) . . . . ?
C5 C4 C9 C8 -0.1(2) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C5 O1 C10 -2.6(2) . . . . ?
C6 C7 C8 C1 179.15(15) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C7 C8 C9 C3 -178.41(15) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C8 C1 C17 C18 147.32(15) . . . . ?
C8 C1 C17 C22 -35.5(2) . . . . ?
C8 C1 N1 C2 53.40(17) . . . . ?
C8 C1 N1 C11 -174.28(13) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C9 C4 C5 O1 -179.63(14) . . . . ?
C17 C1 C8 C7 -73.34(18) . . . . ?
C17 C1 C8 C9 104.64(17) . . . . ?
C17 C1 N1 C2 -71.06(16) . . . . ?
C17 C1 N1 C11 61.26(18) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C18 C19 C20 F4 -179.00(16) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C17 -0.8(3) . . . . ?
C22 C17 C18 C19 0.8(2) . . . . ?
C22 C17 C18 F3 -179.90(14) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C11 C12 C13 F2 -179.97(15) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C12 C11 N1 C1 77.52(18) . . . . ?
C12 C11 N1 C2 -151.91(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C16 C11 C12 F1 179.80(15) . . . . ?
C16 C11 N1 C1 -102.20(18) . . . . ?
C16 C11 N1 C2 28.4(2) . . . . ?
N1 C1 C8 C7 161.86(14) . . . . ?
N1 C1 C8 C9 -20.2(2) . . . . ?
N1 C1 C17 C18 -89.31(18) . . . . ?
N1 C1 C17 C22 87.88(18) . . . . ?
N1 C2 C3 C9 48.80(18) . . . . ?
N1 C11 C12 C13 -179.69(15) . . . . ?
N1 C11 C12 F1 0.1(2) . . . . ?
N1 C11 C16 C15 179.26(15) . . . . ?
O1 C5 C6 C7 -179.79(15) . . . . ?
F3 C18 C19 C20 179.27(15) . . . . ?
F4 C20 C21 C22 -179.93(16) . . . . ?
F1 C12 C13 C14 -179.63(16) . . . . ?
F1 C12 C13 F2 0.3(2) . . . . ?
F2 C13 C14 C15 -179.79(15) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF


data_6-3
_database_code_depnum_ccdc_archive 'CCDC 1540725'
 
_audit_creation_date                    2020-03-09T09:01:05-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          9.642(2)
_cell_length_b                          13.292(2)
_cell_length_c                          13.931(3)
_cell_angle_alpha                       90
_cell_angle_beta                        99.890(9)
_cell_angle_gamma                       90
_cell_volume                            1758.9(6)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4679
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              prism
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.3
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.15
_exptl_crystal_density_diffrn           1.463
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.119
_exptl_absorpt_correction_type          Multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.873
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   14416
_diffrn_reflns_av_R_equivalents         0.029
_diffrn_reflns_theta_min                3.065
_diffrn_reflns_theta_max                25.021
_diffrn_reflns_theta_full               25.021
_diffrn_measured_fraction_theta_max
                                        0.994
_diffrn_measured_fraction_theta_full
                                        0.994
_diffrn_reflns_Laue_measured_fraction_full
                                        0.994
_diffrn_reflns_Laue_measured_fraction_max
                                        0.994
_diffrn_reflns_point_group_measured_fraction_full
                                        0.994
_diffrn_reflns_point_group_measured_fraction_max
                                        0.994
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min              -15
_diffrn_reflns_limit_k_max              15
_diffrn_reflns_limit_l_min              -16
_diffrn_reflns_limit_l_max              16
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3089
_reflns_number_gt                       2773
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0408
_refine_ls_R_factor_gt                  0.0372
_refine_ls_wR_factor_ref                0.1099
_refine_ls_goodness_of_fit_ref          1.11
_refine_ls_restrained_S_all             1.11
_refine_ls_number_reflns                3089
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0649P)²+0.4956P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.271
_refine_diff_density_min                -0.239
_refine_diff_density_rms                0.052
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C1 0.42509(14) 0.12556(10) 0.32106(10) 0.0175(3) Uani d 1 . . C
H1 0.5168 0.0935 0.3494 0.021 Uiso calc 1 . . H
C2 0.32303(14) 0.28884(11) 0.26580(11) 0.0202(3) Uani d 1 . . C
H2A 0.2575 0.2514 0.2159 0.024 Uiso calc 1 . . H
H2B 0.344 0.3545 0.2379 0.024 Uiso calc 1 . . H
C3 0.25684(15) 0.30489(11) 0.35616(11) 0.0214(3) Uani d 1 . . C
H3A 0.3123 0.3557 0.3984 0.026 Uiso calc 1 . . H
H3B 0.1604 0.3317 0.3363 0.026 Uiso calc 1 . . H
C4 0.16258(14) 0.20363(11) 0.48281(10) 0.0200(3) Uani d 1 . . C
H4 0.1066 0.2601 0.4933 0.024 Uiso calc 1 . . H
C5 0.15577(14) 0.11642(11) 0.53704(10) 0.0203(3) Uani d 1 . . C
C6 0.23754(15) 0.03310(11) 0.52300(10) 0.0215(3) Uani d 1 . . C
H6 0.2341 -0.0264 0.5603 0.026 Uiso calc 1 . . H
C7 0.32404(14) 0.03893(11) 0.45334(10) 0.0196(3) Uani d 1 . . C
H7 0.3789 -0.018 0.4424 0.024 Uiso calc 1 . . H
C8 0.33269(14) 0.12601(10) 0.39896(10) 0.0180(3) Uani d 1 . . C
C9 0.25018(14) 0.20928(11) 0.41347(10) 0.0185(3) Uani d 1 . . C
C17 0.35827(14) 0.06318(10) 0.23255(10) 0.0192(3) Uani d 1 . . C
C18 0.43866(15) 0.01454(11) 0.17321(11) 0.0215(3) Uani d 1 . . C
C19 0.38237(17) -0.04163(12) 0.09206(11) 0.0269(3) Uani d 1 . . C
H19 0.4424 -0.0739 0.0541 0.032 Uiso calc 1 . . H
C20 0.23736(17) -0.05019(12) 0.06694(11) 0.0281(4) Uani d 1 . . C
H20 0.1955 -0.0878 0.0115 0.034 Uiso calc 1 . . H
C21 0.15609(16) -0.00228(12) 0.12522(11) 0.0251(3) Uani d 1 . . C
C22 0.21262(15) 0.05384(11) 0.20594(10) 0.0216(3) Uani d 1 . . C
H22 0.1521 0.0862 0.2435 0.026 Uiso calc 1 . . H
C11 0.55496(14) 0.24037(10) 0.23227(10) 0.0177(3) Uani d 1 . . C
C12 0.69652(15) 0.22646(11) 0.27165(10) 0.0194(3) Uani d 1 . . C
C13 0.79948(15) 0.23524(11) 0.21477(11) 0.0222(3) Uani d 1 . . C
C14 0.76698(16) 0.25832(11) 0.11690(11) 0.0237(3) Uani d 1 . . C
H14 0.8387 0.2648 0.0783 0.028 Uiso calc 1 . . H
C15 0.62626(16) 0.27186(11) 0.07646(11) 0.0227(3) Uani d 1 . . C
H15 0.6011 0.287 0.0091 0.027 Uiso calc 1 . . H
C16 0.52201(15) 0.26352(11) 0.13324(11) 0.0206(3) Uani d 1 . . C
H16 0.4265 0.2737 0.1042 0.025 Uiso calc 1 . . H
C10 0.05768(16) 0.03307(12) 0.66242(11) 0.0270(4) Uani d 1 . . C
H10A 0.0256 -0.0249 0.621 0.041 Uiso calc 1 . . H
H10B -0.0087 0.0457 0.707 0.041 Uiso calc 1 . . H
H10C 0.1512 0.019 0.7001 0.041 Uiso calc 1 . . H
N1 0.45407(12) 0.23104(9) 0.29489(9) 0.0182(3) Uani d 1 . . N
O1 0.06491(11) 0.11996(8) 0.60256(7) 0.0250(3) Uani d 1 . . O
F3 0.58141(9) 0.02063(6) 0.19661(7) 0.0270(2) Uani d 1 . . F
F4 0.01399(9) -0.01197(8) 0.10368(7) 0.0356(3) Uani d 1 . . F
F1 0.73577(8) 0.20300(7) 0.36713(6) 0.0249(2) Uani d 1 . . F
F2 0.93510(9) 0.22066(8) 0.25809(7) 0.0326(3) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C1 H1 . 1 ?
C1 C8 . 1.5178(18) ?
C1 C17 . 1.5329(19) ?
C1 N1 . 1.4871(17) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.521(2) ?
C2 N1 . 1.4748(18) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.508(2) ?
C4 H4 . 0.95 ?
C4 C5 . 1.391(2) ?
C4 C9 . 1.390(2) ?
C5 C6 . 1.393(2) ?
C5 O1 . 1.3703(17) ?
C6 H6 . 0.95 ?
C6 C7 . 1.386(2) ?
C7 H7 . 0.95 ?
C7 C8 . 1.394(2) ?
C8 C9 . 1.398(2) ?
C17 C18 . 1.387(2) ?
C17 C22 . 1.395(2) ?
C18 C19 . 1.385(2) ?
C18 F3 . 1.3613(17) ?
C19 H19 . 0.95 ?
C19 C20 . 1.386(2) ?
C20 H20 . 0.95 ?
C20 C21 . 1.377(2) ?
C21 C22 . 1.381(2) ?
C21 F4 . 1.3574(18) ?
C22 H22 . 0.95 ?
C11 C12 . 1.393(2) ?
C11 C16 . 1.396(2) ?
C11 N1 . 1.4192(18) ?
C12 C13 . 1.377(2) ?
C12 F1 . 1.3553(16) ?
C13 C14 . 1.380(2) ?
C13 F2 . 1.3567(17) ?
C14 H14 . 0.95 ?
C14 C15 . 1.389(2) ?
C15 H15 . 0.95 ?
C15 C16 . 1.386(2) ?
C16 H16 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.4333(18) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C8 C1 H1 107.9 . . ?
C8 C1 C17 111.10(11) . . ?
C17 C1 H1 107.9 . . ?
N1 C1 H1 107.9 . . ?
N1 C1 C8 109.25(11) . . ?
N1 C1 C17 112.56(11) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
N1 C2 C3 107.88(11) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C9 C3 C2 112.46(12) . . ?
C9 C3 H3A 109.1 . . ?
C9 C3 H3B 109.1 . . ?
C5 C4 H4 119.6 . . ?
C9 C4 H4 119.6 . . ?
C9 C4 C5 120.88(13) . . ?
C4 C5 C6 120.38(13) . . ?
O1 C5 C4 115.35(13) . . ?
O1 C5 C6 124.27(13) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.50(13) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.75(13) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C1 118.86(12) . . ?
C7 C8 C9 119.37(13) . . ?
C9 C8 C1 121.67(12) . . ?
C4 C9 C3 119.98(12) . . ?
C4 C9 C8 119.11(13) . . ?
C8 C9 C3 120.91(12) . . ?
C18 C17 C1 122.07(13) . . ?
C18 C17 C22 116.13(13) . . ?
C22 C17 C1 121.78(12) . . ?
C19 C18 C17 123.85(14) . . ?
F3 C18 C17 118.38(13) . . ?
F3 C18 C19 117.76(13) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.15(14) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.67(14) . . ?
C21 C20 H20 121.2 . . ?
C20 C21 C22 123.00(14) . . ?
F4 C21 C20 118.73(13) . . ?
F4 C21 C22 118.25(13) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.19(13) . . ?
C21 C22 H22 119.9 . . ?
C12 C11 C16 117.37(13) . . ?
C12 C11 N1 118.36(13) . . ?
C16 C11 N1 124.28(13) . . ?
C13 C12 C11 121.09(13) . . ?
F1 C12 C11 120.43(12) . . ?
F1 C12 C13 118.47(13) . . ?
C12 C13 C14 121.56(14) . . ?
F2 C13 C12 117.82(13) . . ?
F2 C13 C14 120.61(13) . . ?
C13 C14 H14 121 . . ?
C13 C14 C15 118.03(13) . . ?
C15 C14 H14 121 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.80(14) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.16(13) . . ?
C15 C16 H16 119.4 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C2 N1 C1 111.73(11) . . ?
C11 N1 C1 114.24(11) . . ?
C11 N1 C2 115.52(11) . . ?
C5 O1 C10 117.41(12) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C1 C8 C9 C3 -3.9(2) . . . . ?
C1 C8 C9 C4 176.99(12) . . . . ?
C1 C17 C18 C19 -179.30(13) . . . . ?
C1 C17 C18 F3 1.9(2) . . . . ?
C1 C17 C22 C21 179.42(13) . . . . ?
C2 C3 C9 C4 -163.62(12) . . . . ?
C2 C3 C9 C8 17.30(19) . . . . ?
C3 C2 N1 C1 69.64(14) . . . . ?
C3 C2 N1 C11 -157.51(12) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 O1 C10 -177.99(12) . . . . ?
C5 C4 C9 C3 -179.46(13) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C6 C5 O1 C10 2.1(2) . . . . ?
C6 C7 C8 C1 -177.53(12) . . . . ?
C6 C7 C8 C9 -1.2(2) . . . . ?
C7 C8 C9 C3 179.88(12) . . . . ?
C7 C8 C9 C4 0.8(2) . . . . ?
C8 C1 C17 C18 -151.38(13) . . . . ?
C8 C1 C17 C22 29.98(17) . . . . ?
C8 C1 N1 C2 -54.61(14) . . . . ?
C8 C1 N1 C11 171.91(11) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C9 C4 C5 O1 -179.58(12) . . . . ?
C17 C1 C8 C7 72.77(15) . . . . ?
C17 C1 C8 C9 -103.44(14) . . . . ?
C17 C1 N1 C2 69.30(14) . . . . ?
C17 C1 N1 C11 -64.17(15) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C18 C17 C22 C21 0.7(2) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C19 C20 C21 F4 -178.14(13) . . . . ?
C20 C21 C22 C17 -0.8(2) . . . . ?
C22 C17 C18 C19 -0.6(2) . . . . ?
C22 C17 C18 F3 -179.42(12) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 F2 -179.99(12) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C12 C11 N1 C1 -75.28(16) . . . . ?
C12 C11 N1 C2 153.05(13) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C16 C11 C12 F1 -179.45(12) . . . . ?
C16 C11 N1 C1 105.27(15) . . . . ?
C16 C11 N1 C2 -26.41(19) . . . . ?
N1 C1 C8 C7 -162.46(12) . . . . ?
N1 C1 C8 C9 21.32(17) . . . . ?
N1 C1 C17 C18 85.75(16) . . . . ?
N1 C1 C17 C22 -92.90(15) . . . . ?
N1 C2 C3 C9 -47.92(16) . . . . ?
N1 C11 C12 C13 -179.52(12) . . . . ?
N1 C11 C12 F1 1.06(19) . . . . ?
N1 C11 C16 C15 179.72(13) . . . . ?
O1 C5 C6 C7 179.19(13) . . . . ?
F3 C18 C19 C20 179.30(13) . . . . ?
F4 C21 C22 C17 177.99(13) . . . . ?
F1 C12 C13 C14 179.59(13) . . . . ?
F1 C12 C13 F2 -0.6(2) . . . . ?
F2 C13 C14 C15 179.65(13) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF


data_6-4
_database_code_depnum_ccdc_archive 'CCDC 1540731'
 
_audit_creation_date                    2020-03-09T09:02:29-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
_chemical_absolute_configuration        unk
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21 1'
_symmetry_space_group_name_Hall         'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                          8.317(3)
_cell_length_b                          6.0774(19)
_cell_length_c                          17.513(6)
_cell_angle_alpha                       90
_cell_angle_beta                        103.095(13)
_cell_angle_gamma                       90
_cell_volume                            862.2(5)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           2710
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              plate
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           1.492
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    400
_exptl_absorpt_coefficient_mu           0.121
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.92
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   8616
_diffrn_reflns_av_R_equivalents         0.0828
_diffrn_reflns_theta_min                3.051
_diffrn_reflns_theta_max                27.509
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.993
_diffrn_measured_fraction_theta_full
                                        0.994
_diffrn_reflns_Laue_measured_fraction_full
                                        0.994
_diffrn_reflns_Laue_measured_fraction_max
                                        0.993
_diffrn_reflns_point_group_measured_fraction_full
                                        0.994
_diffrn_reflns_point_group_measured_fraction_max
                                        0.987
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -22
_diffrn_reflns_limit_l_max              22
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3898
_reflns_number_gt                       3794
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0453
_refine_ls_R_factor_gt                  0.0448
_refine_ls_wR_factor_ref                0.1219
_refine_ls_goodness_of_fit_ref          1.056
_refine_ls_restrained_S_all             1.056
_refine_ls_number_reflns                3898
_refine_ls_number_parameters            254
_refine_ls_number_restraints            1
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0866P)²+0.0275P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.404
_refine_diff_density_min                -0.284
_refine_diff_density_rms                0.063
_refine_ls_extinction_method            none
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack          0.4(6)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.7071(2) 0.3569(2) 0.80781(8) 0.0274(3) Uani d 1 . . F
F2 0.8323(2) 0.2831(3) 0.95967(8) 0.0321(4) Uani d 1 . . F
F3 0.28875(17) 0.3616(2) 0.83412(7) 0.0215(3) Uani d 1 . . F
F4 0.15793(18) 1.0018(2) 0.67868(8) 0.0238(3) Uani d 1 . . F
O1 0.14935(19) 0.7716(3) 0.38680(8) 0.0186(3) Uani d 1 . . O
N1 0.5307(2) 0.7267(3) 0.75044(10) 0.0158(4) Uani d 1 . . N
C1 0.3743(2) 0.6129(3) 0.71404(11) 0.0143(4) Uani d 1 . . C
H1 0.3937 0.4515 0.7226 0.017 Uiso calc 1 . . H
C2 0.5348(3) 0.9584(4) 0.72693(12) 0.0182(4) Uani d 1 . . C
H2A 0.6374 1.0288 0.7566 0.022 Uiso calc 1 . . H
H2B 0.4396 1.0381 0.7389 0.022 Uiso calc 1 . . H
C3 0.5276(3) 0.9704(4) 0.63894(12) 0.0191(4) Uani d 1 . . C
H3A 0.5066 1.1245 0.6211 0.023 Uiso calc 1 . . H
H3B 0.6361 0.9264 0.6295 0.023 Uiso calc 1 . . H
C4 0.3392(3) 0.8662(4) 0.51033(12) 0.0168(4) Uani d 1 . . C
H4 0.3861 0.9829 0.4865 0.02 Uiso calc 1 . . H
C5 0.2157(3) 0.7372(3) 0.46532(12) 0.0161(4) Uani d 1 . . C
C6 0.1501(3) 0.5591(4) 0.49899(12) 0.0177(4) Uani d 1 . . C
H6 0.0682 0.4676 0.4678 0.021 Uiso calc 1 . . H
C7 0.2069(3) 0.5178(3) 0.57902(12) 0.0170(4) Uani d 1 . . C
H7 0.1629 0.3974 0.6022 0.02 Uiso calc 1 . . H
C8 0.3278(2) 0.6515(3) 0.62562(11) 0.0148(4) Uani d 1 . . C
C9 0.3956(3) 0.8249(3) 0.59135(12) 0.0152(4) Uani d 1 . . C
C10 0.1910(3) 0.9733(4) 0.35462(13) 0.0218(4) Uani d 1 . . C
H10A 0.1264 0.9885 0.3007 0.033 Uiso calc 1 . . H
H10B 0.3089 0.9737 0.3548 0.033 Uiso calc 1 . . H
H10C 0.1664 1.0965 0.3862 0.033 Uiso calc 1 . . H
C11 0.5853(2) 0.6930(4) 0.83329(12) 0.0167(4) Uani d 1 . . C
C12 0.6749(3) 0.5037(4) 0.85966(12) 0.0185(4) Uani d 1 . . C
C13 0.7411(3) 0.4665(4) 0.93928(13) 0.0209(5) Uani d 1 . . C
C14 0.7195(3) 0.6167(4) 0.99515(12) 0.0226(5) Uani d 1 . . C
H14 0.7645 0.5909 1.0493 0.027 Uiso calc 1 . . H
C15 0.6302(3) 0.8072(5) 0.97009(13) 0.0248(5) Uani d 1 . . C
H15 0.6145 0.9134 1.0076 0.03 Uiso calc 1 . . H
C16 0.5627(3) 0.8445(4) 0.88993(13) 0.0217(5) Uani d 1 . . C
H16 0.5009 0.9746 0.8741 0.026 Uiso calc 1 . . H
C17 0.2345(3) 0.6783(4) 0.75435(11) 0.0155(4) Uani d 1 . . C
C18 0.1387(3) 0.8681(4) 0.73814(12) 0.0180(4) Uani d 1 . . C
C19 0.0234(3) 0.9337(4) 0.78008(13) 0.0204(4) Uani d 1 . . C
H19 -0.0381 1.0654 0.7669 0.025 Uiso calc 1 . . H
C20 0.0000(3) 0.8029(4) 0.84152(13) 0.0219(5) Uani d 1 . . C
H20 -0.0767 0.8465 0.8714 0.026 Uiso calc 1 . . H
C21 0.0889(3) 0.6070(4) 0.85981(12) 0.0200(4) Uani d 1 . . C
H21 0.0723 0.5145 0.9011 0.024 Uiso calc 1 . . H
C22 0.2019(3) 0.5525(4) 0.81561(12) 0.0166(4) Uani d 1 . . C
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C12 . 1.343(3) ?
F2 C13 . 1.350(3) ?
F3 C22 . 1.366(2) ?
F4 C18 . 1.358(3) ?
O1 C5 . 1.377(2) ?
O1 C10 . 1.425(3) ?
N1 C1 . 1.483(3) ?
N1 C2 . 1.470(3) ?
N1 C11 . 1.434(3) ?
C1 H1 . 1 ?
C1 C8 . 1.527(3) ?
C1 C17 . 1.543(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.530(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.506(3) ?
C4 H4 . 0.95 ?
C4 C5 . 1.387(3) ?
C4 C9 . 1.412(3) ?
C5 C6 . 1.401(3) ?
C6 H6 . 0.95 ?
C6 C7 . 1.396(3) ?
C7 H7 . 0.95 ?
C7 C8 . 1.402(3) ?
C8 C9 . 1.394(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.391(3) ?
C11 C16 . 1.397(3) ?
C12 C13 . 1.396(3) ?
C13 C14 . 1.380(3) ?
C14 H14 . 0.95 ?
C14 C15 . 1.392(4) ?
C15 H15 . 0.95 ?
C15 C16 . 1.407(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.394(3) ?
C17 C22 . 1.393(3) ?
C18 C19 . 1.392(3) ?
C19 H19 . 0.95 ?
C19 C20 . 1.386(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.400(3) ?
C21 H21 . 0.95 ?
C21 C22 . 1.387(3) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.58(17) . . ?
C2 N1 C1 113.56(17) . . ?
C11 N1 C1 114.47(16) . . ?
C11 N1 C2 113.46(16) . . ?
N1 C1 H1 107.3 . . ?
N1 C1 C8 111.12(15) . . ?
N1 C1 C17 111.22(16) . . ?
C8 C1 H1 107.3 . . ?
C8 C1 C17 112.36(17) . . ?
C17 C1 H1 107.3 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.25(17) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109 . . ?
C2 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
C9 C3 C2 112.73(17) . . ?
C9 C3 H3A 109 . . ?
C9 C3 H3B 109 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C9 120.34(19) . . ?
C9 C4 H4 119.8 . . ?
O1 C5 C4 124.01(18) . . ?
O1 C5 C6 115.56(19) . . ?
C4 C5 C6 120.42(19) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.05(19) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.01(19) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C1 119.01(18) . . ?
C9 C8 C1 121.24(18) . . ?
C9 C8 C7 119.63(18) . . ?
C4 C9 C3 119.10(18) . . ?
C8 C9 C3 121.42(18) . . ?
C8 C9 C4 119.49(18) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 118.49(19) . . ?
C12 C11 C16 117.21(19) . . ?
C16 C11 N1 124.2(2) . . ?
F1 C12 C11 119.92(19) . . ?
F1 C12 C13 118.3(2) . . ?
C11 C12 C13 121.7(2) . . ?
F2 C13 C12 117.9(2) . . ?
F2 C13 C14 121.0(2) . . ?
C14 C13 C12 121.1(2) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 121.0(2) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C1 125.10(18) . . ?
C22 C17 C1 120.61(19) . . ?
C22 C17 C18 114.16(18) . . ?
F4 C18 C17 119.34(18) . . ?
F4 C18 C19 116.6(2) . . ?
C19 C18 C17 124.0(2) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.7(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.38(19) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.72(19) . . ?
C22 C21 H21 121.1 . . ?
F3 C22 C17 117.67(18) . . ?
F3 C22 C21 117.34(18) . . ?
C21 C22 C17 125.0(2) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C12 C13 F2 -0.7(3) . . . . ?
F1 C12 C13 C14 176.7(2) . . . . ?
F2 C13 C14 C15 177.2(2) . . . . ?
F4 C18 C19 C20 -179.7(2) . . . . ?
O1 C5 C6 C7 -177.85(18) . . . . ?
N1 C1 C8 C7 165.26(18) . . . . ?
N1 C1 C8 C9 -18.8(3) . . . . ?
N1 C1 C17 C18 82.4(2) . . . . ?
N1 C1 C17 C22 -93.2(2) . . . . ?
N1 C2 C3 C9 46.9(2) . . . . ?
N1 C11 C12 F1 -0.5(3) . . . . ?
N1 C11 C12 C13 175.89(19) . . . . ?
N1 C11 C16 C15 -175.3(2) . . . . ?
C1 N1 C2 C3 -64.5(2) . . . . ?
C1 N1 C11 C12 83.6(2) . . . . ?
C1 N1 C11 C16 -100.2(2) . . . . ?
C1 C8 C9 C3 5.0(3) . . . . ?
C1 C8 C9 C4 -174.72(18) . . . . ?
C1 C17 C18 F4 5.2(3) . . . . ?
C1 C17 C18 C19 -174.0(2) . . . . ?
C1 C17 C22 F3 -5.1(3) . . . . ?
C1 C17 C22 C21 174.33(19) . . . . ?
C2 N1 C1 C8 49.2(2) . . . . ?
C2 N1 C1 C17 -76.8(2) . . . . ?
C2 N1 C11 C12 -143.8(2) . . . . ?
C2 N1 C11 C16 32.4(3) . . . . ?
C2 C3 C9 C4 160.66(19) . . . . ?
C2 C3 C9 C8 -19.1(3) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
C5 C4 C9 C3 -178.86(19) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C1 174.40(18) . . . . ?
C6 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 C3 -179.05(19) . . . . ?
C7 C8 C9 C4 1.2(3) . . . . ?
C8 C1 C17 C18 -42.9(3) . . . . ?
C8 C1 C17 C22 141.49(19) . . . . ?
C9 C4 C5 O1 177.43(18) . . . . ?
C9 C4 C5 C6 -2.6(3) . . . . ?
C10 O1 C5 C4 -11.3(3) . . . . ?
C10 O1 C5 C6 168.75(18) . . . . ?
C11 N1 C1 C8 -178.28(17) . . . . ?
C11 N1 C1 C17 55.7(2) . . . . ?
C11 N1 C2 C3 162.49(17) . . . . ?
C11 C12 C13 F2 -177.24(19) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
C16 C11 C12 F1 -177.0(2) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C17 C1 C8 C7 -69.4(2) . . . . ?
C17 C1 C8 C9 106.6(2) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C17 C22 F3 178.82(17) . . . . ?
C18 C17 C22 C21 -1.7(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 C22 1.3(3) . . . . ?
C20 C21 C22 F3 179.66(18) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C22 C17 C18 F4 -178.94(19) . . . . ?
C22 C17 C18 C19 1.9(3) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-5
_database_code_depnum_ccdc_archive 'CCDC 1540732'
 
_audit_creation_date                    2020-03-09T09:03:23-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          13.3660(13)
_cell_length_b                          11.6008(10)
_cell_length_c                          30.052(3)
_cell_angle_alpha                       90
_cell_angle_beta                        130.787(3)
_cell_angle_gamma                       90
_cell_volume                            3528.1(6)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           9130
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              irregular
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.3
_exptl_crystal_size_mid                 0.22
_exptl_crystal_size_min                 0.18
_exptl_crystal_density_diffrn           1.459
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1600
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.916
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   18749
_diffrn_reflns_av_R_equivalents         0.0396
_diffrn_reflns_theta_min                3.162
_diffrn_reflns_theta_max                25.026
_diffrn_reflns_theta_full               25.026
_diffrn_measured_fraction_theta_max
                                        0.997
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.997
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.997
_diffrn_reflns_limit_h_min              -15
_diffrn_reflns_limit_h_max              15
_diffrn_reflns_limit_k_min              -13
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -35
_diffrn_reflns_limit_l_max              35
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    6207
_reflns_number_gt                       5326
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.048
_refine_ls_R_factor_gt                  0.0403
_refine_ls_wR_factor_ref                0.1037
_refine_ls_goodness_of_fit_ref          1.054
_refine_ls_restrained_S_all             1.054
_refine_ls_number_reflns                6207
_refine_ls_number_parameters            507
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0457P)²+1.6536P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.215
_refine_diff_density_min                -0.219
_refine_diff_density_rms                0.046
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C1 0.21884(16) 0.07705(14) 0.29761(7) 0.0227(3) Uani d 1 . . C
H1 0.3028 0.0364 0.3142 0.027 Uiso calc 1 . . H
C2 0.11783(16) 0.26892(15) 0.26249(7) 0.0262(4) Uani d 1 . . C
H2A 0.138 0.3523 0.2669 0.031 Uiso calc 1 . . H
H2B 0.0722 0.2532 0.2777 0.031 Uiso calc 1 . . H
C3 0.02950(16) 0.23540(15) 0.19830(8) 0.0279(4) Uani d 1 . . C
H3A -0.0609 0.2643 0.1778 0.033 Uiso calc 1 . . H
H3B 0.0622 0.2732 0.1804 0.033 Uiso calc 1 . . H
C4 -0.06875(16) 0.06195(16) 0.13284(7) 0.0279(4) Uani d 1 . . C
H4 -0.129 0.1125 0.1009 0.033 Uiso calc 1 . . H
C5 -0.07507(17) -0.05518(16) 0.12226(8) 0.0287(4) Uani d 1 . . C
C6 0.01387(17) -0.12973(15) 0.16847(8) 0.0274(4) Uani d 1 . . C
H6 0.011 -0.2101 0.1617 0.033 Uiso calc 1 . . H
C7 0.10702(16) -0.08490(15) 0.22470(7) 0.0254(4) Uani d 1 . . C
H7 0.1677 -0.1357 0.2564 0.03 Uiso calc 1 . . H
C8 0.11375(16) 0.03283(14) 0.23579(7) 0.0232(4) Uani d 1 . . C
C9 0.02356(16) 0.10702(15) 0.18895(7) 0.0244(4) Uani d 1 . . C
C10 -0.1757(2) -0.20627(19) 0.05167(9) 0.0455(5) Uani d 1 . . C
H10A -0.2421 -0.2176 0.009 0.068 Uiso calc 1 . . H
H10B -0.1986 -0.2533 0.071 0.068 Uiso calc 1 . . H
H10C -0.0887 -0.2294 0.0657 0.068 Uiso calc 1 . . H
C11 0.35025(16) 0.24874(14) 0.35101(7) 0.0245(4) Uani d 1 . . C
C12 0.47736(17) 0.21130(15) 0.37719(8) 0.0272(4) Uani d 1 . . C
C13 0.58695(17) 0.25280(17) 0.43072(8) 0.0324(4) Uani d 1 . . C
C14 0.57649(19) 0.33494(18) 0.46041(8) 0.0385(5) Uani d 1 . . C
H14 0.6526 0.3636 0.4973 0.046 Uiso calc 1 . . H
C15 0.4512(2) 0.37470(18) 0.43475(8) 0.0382(5) Uani d 1 . . C
H15 0.4416 0.4321 0.4543 0.046 Uiso calc 1 . . H
C16 0.33991(18) 0.33239(16) 0.38122(8) 0.0301(4) Uani d 1 . . C
H16 0.2552 0.3607 0.3648 0.036 Uiso calc 1 . . H
C17 0.18909(16) 0.04897(14) 0.33770(7) 0.0223(3) Uani d 1 . . C
C18 0.29373(16) 0.02309(14) 0.39653(7) 0.0239(4) Uani d 1 . . C
H18 0.382 0.0244 0.4114 0.029 Uiso calc 1 . . H
C19 0.26872(17) -0.00433(15) 0.43298(7) 0.0268(4) Uani d 1 . . C
C20 0.14135(18) -0.00512(15) 0.41251(8) 0.0278(4) Uani d 1 . . C
C21 0.03692(17) 0.02178(15) 0.35494(8) 0.0277(4) Uani d 1 . . C
H21 -0.0507 0.0226 0.3409 0.033 Uiso calc 1 . . H
C22 0.06079(16) 0.04774(14) 0.31751(7) 0.0246(4) Uani d 1 . . C
H22 -0.0114 0.065 0.2775 0.03 Uiso calc 1 . . H
N1 0.24120(13) 0.20196(12) 0.29603(6) 0.0235(3) Uani d 1 . . N
O1 -0.17243(12) -0.08812(12) 0.06508(5) 0.0367(3) Uani d 1 . . O
F4 0.12230(11) -0.03170(10) 0.44999(5) 0.0408(3) Uani d 1 . . F
F3 0.36983(10) -0.03215(9) 0.48984(4) 0.0358(3) Uani d 1 . . F
F1 0.49554(10) 0.13345(9) 0.34939(5) 0.0347(3) Uani d 1 . . F
F2 0.70710(10) 0.21302(10) 0.45308(5) 0.0439(3) Uani d 1 . . F
C23 0.37651(16) 0.53834(13) 0.26440(7) 0.0217(3) Uani d 1 . . C
H23 0.3418 0.498 0.2813 0.026 Uiso calc 1 . . H
C24 0.36799(17) 0.72893(14) 0.22633(7) 0.0259(4) Uani d 1 . . C
H24A 0.4592 0.7156 0.2421 0.031 Uiso calc 1 . . H
H24B 0.3572 0.8123 0.2291 0.031 Uiso calc 1 . . H
C25 0.26941(17) 0.69040(14) 0.16267(7) 0.0264(4) Uani d 1 . . C
H25A 0.1823 0.7249 0.1442 0.032 Uiso calc 1 . . H
H25B 0.298 0.7201 0.1416 0.032 Uiso calc 1 . . H
C26 0.18376(16) 0.51224(14) 0.10004(7) 0.0250(4) Uani d 1 . . C
H26 0.152 0.56 0.0675 0.03 Uiso calc 1 . . H
C27 0.15904(16) 0.39509(15) 0.09158(7) 0.0252(4) Uani d 1 . . C
C28 0.20782(16) 0.32379(14) 0.13909(7) 0.0256(4) Uani d 1 . . C
H28 0.192 0.2431 0.1337 0.031 Uiso calc 1 . . H
C29 0.27999(15) 0.37237(14) 0.19454(7) 0.0235(3) Uani d 1 . . C
H29 0.3144 0.3238 0.2272 0.028 Uiso calc 1 . . H
C30 0.30317(15) 0.49035(14) 0.20344(7) 0.0215(3) Uani d 1 . . C
C31 0.25406(16) 0.56104(14) 0.15520(7) 0.0232(3) Uani d 1 . . C
C32 0.0378(2) 0.24149(16) 0.02274(8) 0.0373(4) Uani d 1 . . C
H32A -0.0267 0.2293 -0.0199 0.056 Uiso calc 1 . . H
H32B -0.0042 0.227 0.0394 0.056 Uiso calc 1 . . H
H32C 0.1123 0.1885 0.0404 0.056 Uiso calc 1 . . H
C33 0.39700(16) 0.71268(14) 0.31486(7) 0.0245(4) Uani d 1 . . C
C34 0.34683(16) 0.67661(15) 0.34112(7) 0.0271(4) Uani d 1 . . C
C35 0.39475(17) 0.72025(17) 0.39438(8) 0.0311(4) Uani d 1 . . C
C36 0.49246(18) 0.80268(16) 0.42378(8) 0.0333(4) Uani d 1 . . C
H36 0.525 0.8319 0.4607 0.04 Uiso calc 1 . . H
C37 0.54161(18) 0.84145(16) 0.39790(8) 0.0325(4) Uani d 1 . . C
H37 0.608 0.8994 0.4169 0.039 Uiso calc 1 . . H
C38 0.49561(17) 0.79715(15) 0.34458(8) 0.0279(4) Uani d 1 . . C
H38 0.5317 0.8247 0.3279 0.033 Uiso calc 1 . . H
C39 0.52510(16) 0.51766(13) 0.30627(7) 0.0209(3) Uani d 1 . . C
C40 0.59111(16) 0.49473(14) 0.36511(7) 0.0242(4) Uani d 1 . . C
H40 0.5428 0.4882 0.378 0.029 Uiso calc 1 . . H
C41 0.72664(16) 0.48140(14) 0.40470(7) 0.0244(4) Uani d 1 . . C
C42 0.79816(16) 0.49020(14) 0.38643(8) 0.0248(4) Uani d 1 . . C
C43 0.73610(16) 0.51379(14) 0.32911(7) 0.0241(4) Uani d 1 . . C
H43 0.7857 0.5215 0.3169 0.029 Uiso calc 1 . . H
C44 0.59888(16) 0.52649(13) 0.28866(7) 0.0220(3) Uani d 1 . . C
H44 0.5552 0.5414 0.2486 0.026 Uiso calc 1 . . H
N2 0.34520(13) 0.66325(11) 0.26058(6) 0.0231(3) Uani d 1 . . N
O2 0.08430(12) 0.35726(10) 0.03476(5) 0.0320(3) Uani d 1 . . O
F7 0.79186(10) 0.46026(10) 0.46179(4) 0.0358(3) Uani d 1 . . F
F8 0.93073(9) 0.47588(9) 0.42659(4) 0.0326(2) Uani d 1 . . F
F5 0.24758(10) 0.59821(10) 0.31391(4) 0.0346(3) Uani d 1 . . F
F6 0.34051(11) 0.68169(11) 0.41684(5) 0.0459(3) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C1 H1 . 1 ?
C1 C8 . 1.509(2) ?
C1 C17 . 1.530(2) ?
C1 N1 . 1.487(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.514(2) ?
C2 N1 . 1.472(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.508(2) ?
C4 H4 . 0.95 ?
C4 C5 . 1.385(3) ?
C4 C9 . 1.386(2) ?
C5 C6 . 1.390(3) ?
C5 O1 . 1.368(2) ?
C6 H6 . 0.95 ?
C6 C7 . 1.388(2) ?
C7 H7 . 0.95 ?
C7 C8 . 1.395(2) ?
C8 C9 . 1.399(2) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.421(2) ?
C11 C12 . 1.396(2) ?
C11 C16 . 1.396(2) ?
C11 N1 . 1.415(2) ?
C12 C13 . 1.374(3) ?
C12 F1 . 1.356(2) ?
C13 C14 . 1.374(3) ?
C13 F2 . 1.354(2) ?
C14 H14 . 0.95 ?
C14 C15 . 1.388(3) ?
C15 H15 . 0.95 ?
C15 C16 . 1.384(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.393(2) ?
C17 C22 . 1.396(2) ?
C18 H18 . 0.95 ?
C18 C19 . 1.375(2) ?
C19 C20 . 1.382(2) ?
C19 F3 . 1.3542(19) ?
C20 C21 . 1.372(3) ?
C20 F4 . 1.3428(19) ?
C21 H21 . 0.95 ?
C21 C22 . 1.388(2) ?
C22 H22 . 0.95 ?
C23 H23 . 1 ?
C23 C30 . 1.510(2) ?
C23 C39 . 1.523(2) ?
C23 N2 . 1.492(2) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C24 C25 . 1.517(2) ?
C24 N2 . 1.464(2) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C25 C31 . 1.511(2) ?
C26 H26 . 0.95 ?
C26 C27 . 1.382(2) ?
C26 C31 . 1.384(2) ?
C27 C28 . 1.390(2) ?
C27 O2 . 1.370(2) ?
C28 H28 . 0.95 ?
C28 C29 . 1.387(2) ?
C29 H29 . 0.95 ?
C29 C30 . 1.390(2) ?
C30 C31 . 1.401(2) ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C32 O2 . 1.424(2) ?
C33 C34 . 1.392(2) ?
C33 C38 . 1.399(2) ?
C33 N2 . 1.412(2) ?
C34 C35 . 1.374(2) ?
C34 F5 . 1.356(2) ?
C35 C36 . 1.376(3) ?
C35 F6 . 1.349(2) ?
C36 H36 . 0.95 ?
C36 C37 . 1.380(3) ?
C37 H37 . 0.95 ?
C37 C38 . 1.387(3) ?
C38 H38 . 0.95 ?
C39 C40 . 1.392(2) ?
C39 C44 . 1.395(2) ?
C40 H40 . 0.95 ?
C40 C41 . 1.380(2) ?
C41 C42 . 1.382(2) ?
C41 F7 . 1.3451(19) ?
C42 C43 . 1.365(2) ?
C42 F8 . 1.3528(19) ?
C43 H43 . 0.95 ?
C43 C44 . 1.397(2) ?
C44 H44 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C8 C1 H1 107 . . ?
C8 C1 C17 112.66(13) . . ?
C17 C1 H1 107 . . ?
N1 C1 H1 107 . . ?
N1 C1 C8 109.68(13) . . ?
N1 C1 C17 113.19(13) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.23(13) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C9 C3 C2 113.17(14) . . ?
C9 C3 H3A 108.9 . . ?
C9 C3 H3B 108.9 . . ?
C5 C4 H4 119.3 . . ?
C5 C4 C9 121.44(16) . . ?
C9 C4 H4 119.3 . . ?
C4 C5 C6 119.78(16) . . ?
O1 C5 C4 115.32(16) . . ?
O1 C5 C6 124.89(17) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.98(16) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.61(16) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C1 119.33(15) . . ?
C7 C8 C9 118.89(15) . . ?
C9 C8 C1 121.78(15) . . ?
C4 C9 C3 119.73(15) . . ?
C4 C9 C8 119.28(16) . . ?
C8 C9 C3 120.93(15) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C12 C11 C16 116.80(16) . . ?
C12 C11 N1 119.01(15) . . ?
C16 C11 N1 124.18(15) . . ?
C13 C12 C11 121.69(17) . . ?
F1 C12 C11 120.14(15) . . ?
F1 C12 C13 118.16(15) . . ?
C12 C13 C14 121.38(17) . . ?
F2 C13 C12 118.25(17) . . ?
F2 C13 C14 120.34(17) . . ?
C13 C14 H14 121.1 . . ?
C13 C14 C15 117.89(17) . . ?
C15 C14 H14 121.1 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.24(18) . . ?
C16 C15 H15 119.4 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.98(17) . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C1 118.90(14) . . ?
C18 C17 C22 118.62(15) . . ?
C22 C17 C1 122.49(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.72(15) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 121.13(16) . . ?
F3 C19 C18 119.93(15) . . ?
F3 C19 C20 118.95(15) . . ?
C21 C20 C19 120.17(16) . . ?
F4 C20 C19 118.80(16) . . ?
F4 C20 C21 121.03(15) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.20(16) . . ?
C22 C21 H21 120.4 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.15(16) . . ?
C21 C22 H22 119.4 . . ?
C2 N1 C1 112.18(12) . . ?
C11 N1 C1 114.32(13) . . ?
C11 N1 C2 115.84(13) . . ?
C5 O1 C10 116.97(15) . . ?
C30 C23 H23 107.1 . . ?
C30 C23 C39 114.01(13) . . ?
C39 C23 H23 107.1 . . ?
N2 C23 H23 107.1 . . ?
N2 C23 C30 109.73(13) . . ?
N2 C23 C39 111.43(13) . . ?
H24A C24 H24B 108.3 . . ?
C25 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
N2 C24 H24A 109.9 . . ?
N2 C24 H24B 109.9 . . ?
N2 C24 C25 108.97(13) . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C31 C25 C24 113.67(14) . . ?
C31 C25 H25A 108.8 . . ?
C31 C25 H25B 108.8 . . ?
C27 C26 H26 119.5 . . ?
C27 C26 C31 121.05(15) . . ?
C31 C26 H26 119.5 . . ?
C26 C27 C28 120.06(16) . . ?
O2 C27 C26 115.85(14) . . ?
O2 C27 C28 124.09(15) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 C27 118.92(16) . . ?
C29 C28 H28 120.5 . . ?
C28 C29 H29 119.2 . . ?
C28 C29 C30 121.59(15) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C23 118.88(14) . . ?
C29 C30 C31 118.84(15) . . ?
C31 C30 C23 122.25(15) . . ?
C26 C31 C25 120.26(15) . . ?
C26 C31 C30 119.51(15) . . ?
C30 C31 C25 120.09(15) . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
C34 C33 C38 116.77(16) . . ?
C34 C33 N2 118.59(15) . . ?
C38 C33 N2 124.65(15) . . ?
C35 C34 C33 121.25(16) . . ?
F5 C34 C33 120.23(15) . . ?
F5 C34 C35 118.51(15) . . ?
C34 C35 C36 121.90(16) . . ?
F6 C35 C34 117.81(16) . . ?
F6 C35 C36 120.27(16) . . ?
C35 C36 H36 121.1 . . ?
C35 C36 C37 117.78(17) . . ?
C37 C36 H36 121.1 . . ?
C36 C37 H37 119.5 . . ?
C36 C37 C38 121.02(17) . . ?
C38 C37 H37 119.5 . . ?
C33 C38 H38 119.4 . . ?
C37 C38 C33 121.26(16) . . ?
C37 C38 H38 119.4 . . ?
C40 C39 C23 118.81(14) . . ?
C40 C39 C44 118.52(15) . . ?
C44 C39 C23 122.59(14) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.16(15) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 C42 120.53(15) . . ?
F7 C41 C40 120.80(15) . . ?
F7 C41 C42 118.67(15) . . ?
C43 C42 C41 120.54(15) . . ?
F8 C42 C41 118.63(15) . . ?
F8 C42 C43 120.83(15) . . ?
C42 C43 H43 120.3 . . ?
C42 C43 C44 119.31(15) . . ?
C44 C43 H43 120.3 . . ?
C39 C44 C43 120.93(15) . . ?
C39 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C24 N2 C23 112.51(12) . . ?
C33 N2 C23 113.86(13) . . ?
C33 N2 C24 115.51(14) . . ?
C27 O2 C32 117.41(13) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C1 C8 C9 C3 1.1(2) . . . . ?
C1 C8 C9 C4 178.40(14) . . . . ?
C1 C17 C18 C19 -178.87(15) . . . . ?
C1 C17 C22 C21 179.91(16) . . . . ?
C2 C3 C9 C4 169.80(14) . . . . ?
C2 C3 C9 C8 -13.0(2) . . . . ?
C3 C2 N1 C1 -67.13(17) . . . . ?
C3 C2 N1 C11 159.11(14) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C4 C5 O1 C10 175.32(15) . . . . ?
C5 C4 C9 C3 178.34(15) . . . . ?
C5 C4 C9 C8 1.1(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C5 O1 C10 -4.9(2) . . . . ?
C6 C7 C8 C1 -178.78(14) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C3 -178.03(14) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C8 C1 C17 C18 144.54(15) . . . . ?
C8 C1 C17 C22 -35.2(2) . . . . ?
C8 C1 N1 C2 53.70(16) . . . . ?
C8 C1 N1 C11 -171.81(13) . . . . ?
C9 C4 C5 C6 -0.9(2) . . . . ?
C9 C4 C5 O1 178.81(14) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C11 C12 C13 F2 -179.46(15) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C12 C11 N1 C1 65.93(19) . . . . ?
C12 C11 N1 C2 -161.29(14) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C16 C11 C12 C13 1.4(2) . . . . ?
C16 C11 C12 F1 -177.51(14) . . . . ?
C16 C11 N1 C1 -114.95(17) . . . . ?
C16 C11 N1 C2 17.8(2) . . . . ?
C17 C1 C8 C7 -74.25(18) . . . . ?
C17 C1 C8 C9 106.58(17) . . . . ?
C17 C1 N1 C2 -73.04(17) . . . . ?
C17 C1 N1 C11 61.44(17) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C17 C18 C19 F3 178.47(15) . . . . ?
C18 C17 C22 C21 0.2(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C18 C19 C20 F4 -179.53(16) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C17 -1.2(3) . . . . ?
C22 C17 C18 C19 0.8(2) . . . . ?
N1 C1 C8 C7 158.70(13) . . . . ?
N1 C1 C8 C9 -20.46(19) . . . . ?
N1 C1 C17 C18 -90.30(17) . . . . ?
N1 C1 C17 C22 90.01(18) . . . . ?
N1 C2 C3 C9 44.03(18) . . . . ?
N1 C11 C12 C13 -179.44(15) . . . . ?
N1 C11 C12 F1 1.7(2) . . . . ?
N1 C11 C16 C15 -179.61(16) . . . . ?
O1 C5 C6 C7 -179.18(15) . . . . ?
F4 C20 C21 C22 -179.42(16) . . . . ?
F3 C19 C20 C21 -179.45(16) . . . . ?
F3 C19 C20 F4 1.0(2) . . . . ?
F1 C12 C13 C14 177.59(16) . . . . ?
F1 C12 C13 F2 -0.6(2) . . . . ?
F2 C13 C14 C15 178.40(16) . . . . ?
C23 C30 C31 C25 -2.2(2) . . . . ?
C23 C30 C31 C26 -177.83(14) . . . . ?
C23 C39 C40 C41 -176.72(15) . . . . ?
C23 C39 C44 C43 176.08(14) . . . . ?
C24 C25 C31 C26 -169.97(14) . . . . ?
C24 C25 C31 C30 14.4(2) . . . . ?
C25 C24 N2 C23 66.76(17) . . . . ?
C25 C24 N2 C33 -160.16(13) . . . . ?
C26 C27 C28 C29 0.6(2) . . . . ?
C26 C27 O2 C32 -169.50(15) . . . . ?
C27 C26 C31 C25 -174.40(15) . . . . ?
C27 C26 C31 C30 1.3(2) . . . . ?
C27 C28 C29 C30 0.7(2) . . . . ?
C28 C27 O2 C32 9.7(2) . . . . ?
C28 C29 C30 C23 176.91(14) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C29 C30 C31 C25 175.77(14) . . . . ?
C29 C30 C31 C26 0.1(2) . . . . ?
C30 C23 C39 C40 -143.68(15) . . . . ?
C30 C23 C39 C44 39.6(2) . . . . ?
C30 C23 N2 C24 -53.10(17) . . . . ?
C30 C23 N2 C33 173.02(13) . . . . ?
C31 C26 C27 C28 -1.6(2) . . . . ?
C31 C26 C27 O2 177.63(14) . . . . ?
C33 C34 C35 C36 1.1(3) . . . . ?
C33 C34 C35 F6 179.54(15) . . . . ?
C34 C33 C38 C37 0.7(2) . . . . ?
C34 C33 N2 C23 -66.97(18) . . . . ?
C34 C33 N2 C24 160.58(15) . . . . ?
C34 C35 C36 C37 0.3(3) . . . . ?
C35 C36 C37 C38 -1.2(3) . . . . ?
C36 C37 C38 C33 0.7(3) . . . . ?
C38 C33 C34 C35 -1.6(2) . . . . ?
C38 C33 C34 F5 177.50(14) . . . . ?
C38 C33 N2 C23 113.62(17) . . . . ?
C38 C33 N2 C24 -18.8(2) . . . . ?
C39 C23 C30 C29 76.55(18) . . . . ?
C39 C23 C30 C31 -105.52(17) . . . . ?
C39 C23 N2 C24 74.14(16) . . . . ?
C39 C23 N2 C33 -59.74(17) . . . . ?
C39 C40 C41 C42 -0.2(2) . . . . ?
C39 C40 C41 F7 179.39(15) . . . . ?
C40 C39 C44 C43 -0.6(2) . . . . ?
C40 C41 C42 C43 0.9(2) . . . . ?
C40 C41 C42 F8 -179.61(14) . . . . ?
C41 C42 C43 C44 -1.4(2) . . . . ?
C42 C43 C44 C39 1.3(2) . . . . ?
C44 C39 C40 C41 0.1(2) . . . . ?
N2 C23 C30 C29 -157.67(14) . . . . ?
N2 C23 C30 C31 20.3(2) . . . . ?
N2 C23 C39 C40 91.44(17) . . . . ?
N2 C23 C39 C44 -85.25(18) . . . . ?
N2 C24 C25 C31 -44.91(18) . . . . ?
N2 C33 C34 C35 178.97(15) . . . . ?
N2 C33 C34 F5 -2.0(2) . . . . ?
N2 C33 C38 C37 -179.90(15) . . . . ?
O2 C27 C28 C29 -178.57(15) . . . . ?
F7 C41 C42 C43 -178.73(15) . . . . ?
F7 C41 C42 F8 0.7(2) . . . . ?
F8 C42 C43 C44 179.13(14) . . . . ?
F5 C34 C35 C36 -177.95(16) . . . . ?
F5 C34 C35 F6 0.4(2) . . . . ?
F6 C35 C36 C37 -178.10(16) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-6
_database_code_depnum_ccdc_archive 'CCDC 1540733'
 
_audit_creation_date                    2020-03-09T09:04:17-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'C 1 2/c 1'
_symmetry_space_group_name_Hall         '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                          22.323(8)
_cell_length_b                          13.499(5)
_cell_length_c                          11.828(5)
_cell_angle_alpha                       90
_cell_angle_beta                        98.459(17)
_cell_angle_gamma                       90
_cell_volume                            3526(2)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           4165
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.4
_cell_measurement_temperature           100
_exptl_crystal_description              needle
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.1
_exptl_crystal_density_diffrn           1.46
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1600
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.713
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   10335
_diffrn_reflns_av_R_equivalents         0.0774
_diffrn_reflns_theta_min                3.018
_diffrn_reflns_theta_max                27.472
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.994
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.994
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.994
_diffrn_reflns_limit_h_min              -28
_diffrn_reflns_limit_h_max              28
_diffrn_reflns_limit_k_min              -17
_diffrn_reflns_limit_k_max              17
_diffrn_reflns_limit_l_min              -15
_diffrn_reflns_limit_l_max              13
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4010
_reflns_number_gt                       2301
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.094
_refine_ls_R_factor_gt                  0.0567
_refine_ls_wR_factor_ref                0.1371
_refine_ls_goodness_of_fit_ref          0.953
_refine_ls_restrained_S_all             0.953
_refine_ls_number_reflns                4010
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.282
_refine_diff_density_min                -0.316
_refine_diff_density_rms                0.057
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.57206(6) 0.27905(11) 0.35110(10) 0.0487(4) Uani d 1 . . F
F2 0.56593(6) 0.08251(11) 0.33378(12) 0.0597(4) Uani d 1 . . F
F3 0.78495(6) 0.16624(12) 0.67940(10) 0.0537(4) Uani d 1 . . F
F4 0.80789(5) 0.49115(11) 0.82131(11) 0.0547(4) Uani d 1 . . F
O1 0.62123(6) 0.83390(12) 0.46662(13) 0.0411(4) Uani d 1 . . O
N1 0.57938(7) 0.37686(15) 0.55817(13) 0.0336(4) Uani d 1 . . N
C1 0.63623(8) 0.41640(17) 0.52456(16) 0.0322(5) Uani d 1 . . C
H1 0.6401 0.3872 0.4483 0.039 Uiso calc 1 . . H
C2 0.56389(9) 0.42765(18) 0.66019(16) 0.0378(6) Uani d 1 . . C
H2A 0.5985 0.4235 0.7228 0.045 Uiso calc 1 . . H
H2B 0.5287 0.3946 0.686 0.045 Uiso calc 1 . . H
C3 0.54879(9) 0.53591(18) 0.63334(17) 0.0357(6) Uani d 1 . . C
H3A 0.5067 0.5404 0.5935 0.043 Uiso calc 1 . . H
H3B 0.551 0.573 0.706 0.043 Uiso calc 1 . . H
C4 0.58813(8) 0.68581(18) 0.54228(16) 0.0354(6) Uani d 1 . . C
H4 0.5597 0.7243 0.5756 0.042 Uiso calc 1 . . H
C5 0.62674(9) 0.73243(19) 0.47644(17) 0.0356(5) Uani d 1 . . C
C6 0.66779(9) 0.67609(19) 0.42611(16) 0.0358(6) Uani d 1 . . C
H6 0.6943 0.7068 0.3809 0.043 Uiso calc 1 . . H
C7 0.66939(9) 0.57458(19) 0.44291(16) 0.0361(6) Uani d 1 . . C
H7 0.6976 0.5362 0.4087 0.043 Uiso calc 1 . . H
C8 0.63099(8) 0.52670(18) 0.50841(16) 0.0313(5) Uani d 1 . . C
C9 0.59056(8) 0.58428(18) 0.56003(16) 0.0319(5) Uani d 1 . . C
C10 0.66642(10) 0.8848(2) 0.41514(19) 0.0454(6) Uani d 1 . . C
H10A 0.6633 0.8655 0.3346 0.068 Uiso calc 1 . . H
H10B 0.7067 0.8673 0.4551 0.068 Uiso calc 1 . . H
H10C 0.6603 0.9564 0.4204 0.068 Uiso calc 1 . . H
C11 0.57253(8) 0.27336(18) 0.55267(18) 0.0349(5) Uani d 1 . . C
C12 0.57032(9) 0.22502(19) 0.44788(18) 0.0391(6) Uani d 1 . . C
C13 0.56650(10) 0.1236(2) 0.4390(2) 0.0455(6) Uani d 1 . . C
C14 0.56326(9) 0.0645(2) 0.5321(2) 0.0506(7) Uani d 1 . . C
H14 0.5618 -0.0056 0.5255 0.061 Uiso calc 1 . . H
C15 0.56222(10) 0.1112(2) 0.6368(2) 0.0497(7) Uani d 1 . . C
H15 0.5579 0.0724 0.7021 0.06 Uiso calc 1 . . H
C16 0.56729(9) 0.2126(2) 0.64755(19) 0.0417(6) Uani d 1 . . C
H16 0.5673 0.2422 0.7204 0.05 Uiso calc 1 . . H
C17 0.69308(8) 0.38555(19) 0.60696(16) 0.0349(6) Uani d 1 . . C
C18 0.72549(8) 0.4542(2) 0.68005(17) 0.0375(6) Uani d 1 . . C
H18 0.7124 0.5211 0.6813 0.045 Uiso calc 1 . . H
C19 0.77678(9) 0.4232(2) 0.75037(17) 0.0420(6) Uani d 1 . . C
C20 0.79861(10) 0.3276(2) 0.75261(18) 0.0463(7) Uani d 1 . . C
H20 0.8345 0.3085 0.8011 0.056 Uiso calc 1 . . H
C21 0.76531(9) 0.2618(2) 0.68036(18) 0.0421(6) Uani d 1 . . C
C22 0.71334(9) 0.28752(19) 0.60739(17) 0.0380(6) Uani d 1 . . C
H22 0.6919 0.2395 0.5585 0.046 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C12 . 1.363(3) ?
F2 C13 . 1.361(3) ?
F3 C21 . 1.363(3) ?
F4 C19 . 1.363(3) ?
O1 C5 . 1.379(3) ?
O1 C10 . 1.429(2) ?
N1 C1 . 1.484(2) ?
N1 C2 . 1.473(2) ?
N1 C11 . 1.406(3) ?
C1 H1 . 1 ?
C1 C8 . 1.504(3) ?
C1 C17 . 1.540(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.523(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.512(3) ?
C4 H4 . 0.95 ?
C4 C5 . 1.394(3) ?
C4 C9 . 1.386(3) ?
C5 C6 . 1.390(3) ?
C6 H6 . 0.95 ?
C6 C7 . 1.384(3) ?
C7 H7 . 0.95 ?
C7 C8 . 1.396(3) ?
C8 C9 . 1.398(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.395(3) ?
C11 C16 . 1.408(3) ?
C12 C13 . 1.375(4) ?
C13 C14 . 1.371(4) ?
C14 H14 . 0.95 ?
C14 C15 . 1.392(3) ?
C15 H15 . 0.95 ?
C15 C16 . 1.378(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(3) ?
C17 C22 . 1.398(3) ?
C18 H18 . 0.95 ?
C18 C19 . 1.378(3) ?
C19 C20 . 1.377(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.373(3) ?
C21 C22 . 1.385(3) ?
C22 H22 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.99(17) . . ?
C2 N1 C1 111.42(17) . . ?
C11 N1 C1 115.89(16) . . ?
C11 N1 C2 117.62(17) . . ?
N1 C1 H1 106.9 . . ?
N1 C1 C8 109.67(16) . . ?
N1 C1 C17 113.01(16) . . ?
C8 C1 H1 106.9 . . ?
C8 C1 C17 112.95(18) . . ?
C17 C1 H1 106.9 . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C3 110.33(17) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C9 C3 C2 113.45(17) . . ?
C9 C3 H3A 108.9 . . ?
C9 C3 H3B 108.9 . . ?
C5 C4 H4 119.4 . . ?
C9 C4 H4 119.4 . . ?
C9 C4 C5 121.16(19) . . ?
O1 C5 C4 116.16(19) . . ?
O1 C5 C6 124.3(2) . . ?
C6 C5 C4 119.5(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C1 119.10(18) . . ?
C7 C8 C9 118.3(2) . . ?
C9 C8 C1 122.58(19) . . ?
C4 C9 C3 120.01(18) . . ?
C4 C9 C8 119.8(2) . . ?
C8 C9 C3 120.2(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C16 124.2(2) . . ?
C12 C11 N1 119.7(2) . . ?
C12 C11 C16 116.1(2) . . ?
F1 C12 C11 119.6(2) . . ?
F1 C12 C13 118.5(2) . . ?
C13 C12 C11 121.8(2) . . ?
F2 C13 C12 117.9(2) . . ?
F2 C13 C14 120.2(3) . . ?
C14 C13 C12 121.9(2) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.4(3) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C1 121.1(2) . . ?
C18 C17 C22 119.25(19) . . ?
C22 C17 C1 119.6(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
F4 C19 C18 118.0(2) . . ?
F4 C19 C20 118.15(19) . . ?
C20 C19 C18 123.8(2) . . ?
C19 C20 H20 122.1 . . ?
C21 C20 C19 115.9(2) . . ?
C21 C20 H20 122.1 . . ?
F3 C21 C20 118.2(2) . . ?
F3 C21 C22 118.2(2) . . ?
C20 C21 C22 123.5(2) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 C17 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C12 C13 F2 1.3(3) . . . . ?
F1 C12 C13 C14 -178.59(18) . . . . ?
F2 C13 C14 C15 -178.14(18) . . . . ?
F3 C21 C22 C17 -179.45(16) . . . . ?
F4 C19 C20 C21 179.39(17) . . . . ?
O1 C5 C6 C7 179.50(18) . . . . ?
N1 C1 C8 C7 -159.54(17) . . . . ?
N1 C1 C8 C9 22.9(2) . . . . ?
N1 C1 C17 C18 -109.0(2) . . . . ?
N1 C1 C17 C22 72.1(2) . . . . ?
N1 C2 C3 C9 -41.3(2) . . . . ?
N1 C11 C12 F1 -3.0(3) . . . . ?
N1 C11 C12 C13 176.92(18) . . . . ?
N1 C11 C16 C15 -178.32(18) . . . . ?
C1 N1 C2 C3 65.9(2) . . . . ?
C1 N1 C11 C12 -62.1(2) . . . . ?
C1 N1 C11 C16 118.2(2) . . . . ?
C1 C8 C9 C3 -1.4(3) . . . . ?
C1 C8 C9 C4 179.63(18) . . . . ?
C1 C17 C18 C19 -178.63(17) . . . . ?
C1 C17 C22 C21 178.60(17) . . . . ?
C2 N1 C1 C8 -55.0(2) . . . . ?
C2 N1 C1 C17 72.0(2) . . . . ?
C2 N1 C11 C12 162.53(17) . . . . ?
C2 N1 C11 C16 -17.2(3) . . . . ?
C2 C3 C9 C4 -170.65(17) . . . . ?
C2 C3 C9 C8 10.4(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C4 C9 C3 179.05(18) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C1 -178.86(18) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C3 -179.01(17) . . . . ?
C7 C8 C9 C4 2.1(3) . . . . ?
C8 C1 C17 C18 16.2(2) . . . . ?
C8 C1 C17 C22 -162.66(17) . . . . ?
C9 C4 C5 O1 -178.63(17) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C10 O1 C5 C4 170.38(17) . . . . ?
C10 O1 C5 C6 -9.3(3) . . . . ?
C11 N1 C1 C8 166.97(16) . . . . ?
C11 N1 C1 C17 -66.0(2) . . . . ?
C11 N1 C2 C3 -156.81(16) . . . . ?
C11 C12 C13 F2 -178.55(17) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C11 C16 C15 2.0(3) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
C13 C14 C15 C16 -3.2(3) . . . . ?
C14 C15 C16 C11 1.3(3) . . . . ?
C16 C11 C12 F1 176.77(17) . . . . ?
C16 C11 C12 C13 -3.3(3) . . . . ?
C17 C1 C8 C7 73.4(2) . . . . ?
C17 C1 C8 C9 -104.1(2) . . . . ?
C17 C18 C19 F4 -179.95(17) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 F3 -179.93(17) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF


data_6-7
_database_code_depnum_ccdc_archive 'CCDC 1540734'
 
_audit_creation_date                    2020-03-09T09:05:29-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'C 1 2/c 1'
_symmetry_space_group_name_Hall         '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                          36.448(11)
_cell_length_b                          6.1171(18)
_cell_length_c                          16.087(4)
_cell_angle_alpha                       90
_cell_angle_beta                        102.193(7)
_cell_angle_gamma                       90
_cell_volume                            3505.8(17)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           3917
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              irregular
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.35
_exptl_crystal_size_mid                 0.23
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           1.468
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1600
_exptl_absorpt_coefficient_mu           0.119
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.691
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   11505
_diffrn_reflns_av_R_equivalents         0.0596
_diffrn_reflns_theta_min                3.045
_diffrn_reflns_theta_max                27.455
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.993
_diffrn_measured_fraction_theta_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_max
                                        0.993
_diffrn_reflns_point_group_measured_fraction_full
                                        0.995
_diffrn_reflns_point_group_measured_fraction_max
                                        0.993
_diffrn_reflns_limit_h_min              -46
_diffrn_reflns_limit_h_max              46
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -20
_diffrn_reflns_limit_l_max              20
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3977
_reflns_number_gt                       2690
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0831
_refine_ls_R_factor_gt                  0.0524
_refine_ls_wR_factor_ref                0.1454
_refine_ls_goodness_of_fit_ref          1.048
_refine_ls_restrained_S_all             1.048
_refine_ls_number_reflns                3977
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0708P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.335
_refine_diff_density_min                -0.237
_refine_diff_density_rms                0.065
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.59602(3) 0.95814(18) 0.38999(7) 0.0261(3) Uani d 1 . . F
F2 0.47742(3) 0.6285(2) 0.34858(9) 0.0373(4) Uani d 1 . . F
F3 0.57829(3) 0.98567(19) 0.57399(7) 0.0277(3) Uani d 1 . . F
F4 0.54055(3) 0.8947(2) 0.69409(8) 0.0318(3) Uani d 1 . . F
O1 0.80288(4) 0.7269(2) 0.68283(9) 0.0253(3) Uani d 1 . . O
N1 0.63080(4) 0.6142(3) 0.48493(9) 0.0186(4) Uani d 1 . . N
C1 0.64523(5) 0.7681(3) 0.55582(11) 0.0185(4) Uani d 1 . . C
H1 0.6388 0.9195 0.5342 0.022 Uiso calc 1 . . H
C2 0.64743(6) 0.3954(3) 0.49970(12) 0.0214(4) Uani d 1 . . C
H2A 0.6349 0.2939 0.4547 0.026 Uiso calc 1 . . H
H2B 0.6441 0.3385 0.5553 0.026 Uiso calc 1 . . H
C3 0.68883(6) 0.4114(3) 0.49884(12) 0.0222(4) Uani d 1 . . C
H3A 0.701 0.2684 0.5152 0.027 Uiso calc 1 . . H
H3B 0.6918 0.4459 0.4405 0.027 Uiso calc 1 . . H
C4 0.74696(6) 0.5734(3) 0.59044(12) 0.0206(4) Uani d 1 . . C
H4 0.7609 0.4565 0.5734 0.025 Uiso calc 1 . . H
C5 0.76521(6) 0.7311(3) 0.64615(12) 0.0202(4) Uani d 1 . . C
C6 0.74498(6) 0.9051(3) 0.66921(12) 0.0228(4) Uani d 1 . . C
H6 0.7575 1.0161 0.7059 0.027 Uiso calc 1 . . H
C7 0.70670(6) 0.9160(3) 0.63862(12) 0.0207(4) Uani d 1 . . C
H7 0.693 1.0345 0.6551 0.025 Uiso calc 1 . . H
C8 0.68763(6) 0.7553(3) 0.58351(12) 0.0195(4) Uani d 1 . . C
C9 0.70817(6) 0.5857(3) 0.55933(11) 0.0195(4) Uani d 1 . . C
C10 0.82382(6) 0.5440(4) 0.66357(13) 0.0273(5) Uani d 1 . . C
H10A 0.8241 0.5444 0.6028 0.041 Uiso calc 1 . . H
H10B 0.8122 0.4086 0.678 0.041 Uiso calc 1 . . H
H10C 0.8496 0.5532 0.6967 0.041 Uiso calc 1 . . H
C11 0.59115(5) 0.6164(3) 0.45497(11) 0.0177(4) Uani d 1 . . C
C12 0.57401(6) 0.7892(3) 0.40479(12) 0.0212(4) Uani d 1 . . C
C13 0.53630(6) 0.7991(3) 0.36913(12) 0.0240(4) Uani d 1 . . C
H13 0.5256 0.9207 0.3359 0.029 Uiso calc 1 . . H
C14 0.51469(6) 0.6248(3) 0.38384(13) 0.0254(5) Uani d 1 . . C
C15 0.52950(6) 0.4495(4) 0.43334(13) 0.0258(5) Uani d 1 . . C
H15 0.5139 0.3318 0.4427 0.031 Uiso calc 1 . . H
C16 0.56768(6) 0.4474(3) 0.46939(12) 0.0216(4) Uani d 1 . . C
H16 0.578 0.3283 0.5046 0.026 Uiso calc 1 . . H
C17 0.62625(5) 0.7310(3) 0.63132(11) 0.0184(4) Uani d 1 . . C
C18 0.59305(5) 0.8351(3) 0.63422(11) 0.0192(4) Uani d 1 . . C
C19 0.57360(6) 0.7914(3) 0.69681(12) 0.0215(4) Uani d 1 . . C
C20 0.58698(6) 0.6440(3) 0.76013(12) 0.0231(4) Uani d 1 . . C
H20 0.5733 0.6134 0.803 0.028 Uiso calc 1 . . H
C21 0.62070(6) 0.5407(3) 0.76040(12) 0.0226(4) Uani d 1 . . C
H21 0.6306 0.44 0.8044 0.027 Uiso calc 1 . . H
C22 0.64016(6) 0.5831(3) 0.69697(11) 0.0203(4) Uani d 1 . . C
H22 0.6633 0.5108 0.698 0.024 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C12 . 1.359(2) ?
F2 C14 . 1.357(2) ?
F3 C18 . 1.363(2) ?
F4 C19 . 1.353(2) ?
O1 C5 . 1.375(2) ?
O1 C10 . 1.425(2) ?
N1 C1 . 1.487(2) ?
N1 C2 . 1.468(2) ?
N1 C11 . 1.423(2) ?
C1 H1 . 1 ?
C1 C8 . 1.517(3) ?
C1 C17 . 1.536(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.515(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.513(3) ?
C4 H4 . 0.95 ?
C4 C5 . 1.388(3) ?
C4 C9 . 1.399(3) ?
C5 C6 . 1.389(3) ?
C6 H6 . 0.95 ?
C6 C7 . 1.380(3) ?
C7 H7 . 0.95 ?
C7 C8 . 1.405(3) ?
C8 C9 . 1.383(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.395(3) ?
C11 C16 . 1.392(3) ?
C12 C13 . 1.374(3) ?
C13 H13 . 0.95 ?
C13 C14 . 1.376(3) ?
C14 C15 . 1.376(3) ?
C15 H15 . 0.95 ?
C15 C16 . 1.390(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.377(3) ?
C17 C22 . 1.402(3) ?
C18 C19 . 1.375(3) ?
C19 C20 . 1.371(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.381(3) ?
C21 H21 . 0.95 ?
C21 C22 . 1.385(3) ?
C22 H22 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.99(16) . . ?
C2 N1 C1 112.72(15) . . ?
C11 N1 C1 115.02(15) . . ?
C11 N1 C2 114.75(16) . . ?
N1 C1 H1 107.5 . . ?
N1 C1 C8 111.47(15) . . ?
N1 C1 C17 111.57(15) . . ?
C8 C1 H1 107.5 . . ?
C8 C1 C17 111.17(15) . . ?
C17 C1 H1 107.5 . . ?
N1 C2 H2A 110 . . ?
N1 C2 H2B 110 . . ?
N1 C2 C3 108.53(16) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110 . . ?
C3 C2 H2B 110 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108 . . ?
C9 C3 C2 111.65(16) . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C9 120.27(18) . . ?
C9 C4 H4 119.9 . . ?
O1 C5 C4 124.25(18) . . ?
O1 C5 C6 115.97(17) . . ?
C4 C5 C6 119.77(19) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.70(18) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.28(18) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C1 119.11(17) . . ?
C9 C8 C1 122.30(18) . . ?
C9 C8 C7 118.53(18) . . ?
C4 C9 C3 119.36(17) . . ?
C8 C9 C3 120.23(18) . . ?
C8 C9 C4 120.40(18) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 120.11(17) . . ?
C16 C11 N1 123.50(17) . . ?
C16 C11 C12 116.32(18) . . ?
F1 C12 C11 117.94(17) . . ?
F1 C12 C13 117.94(17) . . ?
C13 C12 C11 124.12(18) . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 116.91(19) . . ?
C14 C13 H13 121.5 . . ?
F2 C14 C13 118.28(19) . . ?
F2 C14 C15 119.39(19) . . ?
C13 C14 C15 122.3(2) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.98(19) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.32(19) . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C1 120.28(16) . . ?
C18 C17 C22 116.96(17) . . ?
C22 C17 C1 122.65(17) . . ?
F3 C18 C17 120.42(16) . . ?
F3 C18 C19 117.71(17) . . ?
C19 C18 C17 121.87(17) . . ?
F4 C19 C18 118.62(17) . . ?
F4 C19 C20 120.41(17) . . ?
C20 C19 C18 120.97(18) . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.68(18) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.40(18) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.08(18) . . ?
C21 C22 H22 119.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C12 C13 C14 178.98(16) . . . . ?
F2 C14 C15 C16 -179.80(17) . . . . ?
F3 C18 C19 F4 1.8(3) . . . . ?
F3 C18 C19 C20 -179.14(18) . . . . ?
F4 C19 C20 C21 179.57(18) . . . . ?
O1 C5 C6 C7 -176.82(16) . . . . ?
N1 C1 C8 C7 168.43(16) . . . . ?
N1 C1 C8 C9 -14.4(2) . . . . ?
N1 C1 C17 C18 -87.3(2) . . . . ?
N1 C1 C17 C22 88.8(2) . . . . ?
N1 C2 C3 C9 52.6(2) . . . . ?
N1 C11 C12 F1 -3.6(3) . . . . ?
N1 C11 C12 C13 176.16(17) . . . . ?
N1 C11 C16 C15 -175.00(17) . . . . ?
C1 N1 C2 C3 -66.53(19) . . . . ?
C1 N1 C11 C12 74.8(2) . . . . ?
C1 N1 C11 C16 -108.5(2) . . . . ?
C1 C8 C9 C3 3.9(3) . . . . ?
C1 C8 C9 C4 -176.13(16) . . . . ?
C1 C17 C18 F3 -5.5(3) . . . . ?
C1 C17 C18 C19 174.20(18) . . . . ?
C1 C17 C22 C21 -174.71(18) . . . . ?
C2 N1 C1 C8 46.0(2) . . . . ?
C2 N1 C1 C17 -78.91(19) . . . . ?
C2 N1 C11 C12 -152.01(17) . . . . ?
C2 N1 C11 C16 24.7(2) . . . . ?
C2 C3 C9 C4 157.03(17) . . . . ?
C2 C3 C9 C8 -23.0(2) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C5 C4 C9 C3 -179.81(17) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C1 176.48(17) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C3 -178.92(17) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C8 C1 C17 C18 147.59(18) . . . . ?
C8 C1 C17 C22 -36.3(2) . . . . ?
C9 C4 C5 O1 176.97(16) . . . . ?
C9 C4 C5 C6 -1.8(3) . . . . ?
C10 O1 C5 C4 -1.9(3) . . . . ?
C10 O1 C5 C6 176.85(16) . . . . ?
C11 N1 C1 C8 -179.84(15) . . . . ?
C11 N1 C1 C17 55.2(2) . . . . ?
C11 N1 C2 C3 159.21(15) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C11 C16 C15 1.9(3) . . . . ?
C12 C13 C14 F2 -179.19(17) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C16 C11 C12 F1 179.42(15) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C17 C1 C8 C7 -66.4(2) . . . . ?
C17 C1 C8 C9 110.77(19) . . . . ?
C17 C18 C19 F4 -177.91(18) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C17 C22 C21 1.5(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 F3 178.16(16) . . . . ?
C22 C17 C18 C19 -2.1(3) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-8
_database_code_depnum_ccdc_archive 'CCDC 1540735'
 
_audit_creation_date                    2020-03-09T09:06:26-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
_chemical_absolute_configuration        unk
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P c a 21'
_symmetry_space_group_name_Hall         'P 2c -2ac'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y, z'
 '-x+1/2, y, z+1/2'

_cell_length_a                          16.559(2)
_cell_length_b                          17.595(2)
_cell_length_c                          6.1048(9)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1778.7(4)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4920
_cell_measurement_theta_min             3.3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              needle
_exptl_crystal_colour                   'clear yellowish yellow'
_exptl_crystal_size_max                 0.35
_exptl_crystal_size_mid                 0.25
_exptl_crystal_size_min                 0.15
_exptl_crystal_density_diffrn           1.446
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.117
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.88
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   15664
_diffrn_reflns_av_R_equivalents         0.0411
_diffrn_reflns_theta_min                3.379
_diffrn_reflns_theta_max                27.484
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.997
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.997
_diffrn_reflns_point_group_measured_fraction_full
                                        0.998
_diffrn_reflns_point_group_measured_fraction_max
                                        0.999
_diffrn_reflns_limit_h_min              -21
_diffrn_reflns_limit_h_max              20
_diffrn_reflns_limit_k_min              -22
_diffrn_reflns_limit_k_max              22
_diffrn_reflns_limit_l_min              -7
_diffrn_reflns_limit_l_max              7
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4061
_reflns_number_gt                       3654
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0496
_refine_ls_R_factor_gt                  0.0438
_refine_ls_wR_factor_ref                0.1058
_refine_ls_goodness_of_fit_ref          1.073
_refine_ls_restrained_S_all             1.073
_refine_ls_number_reflns                4061
_refine_ls_number_parameters            254
_refine_ls_number_restraints            1
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0509P)²+0.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.267
_refine_diff_density_min                -0.219
_refine_diff_density_rms                0.047
_refine_ls_extinction_method            none
_refine_ls_abs_structure_details
;
 Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          -0.1(4)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C19 0.61840(17) 0.17114(16) 0.3861(5) 0.0246(6) Uani d 1 . . C
H19 0.6409 0.1328 0.295 0.03 Uiso calc 1 . . H
C11 0.37187(16) 0.15200(16) 0.5475(5) 0.0214(5) Uani d 1 . . C
C18 0.54189(16) 0.19998(15) 0.3514(5) 0.0221(5) Uani d 1 . . C
C9 0.35821(15) 0.38841(15) 0.6540(5) 0.0213(5) Uani d 1 . . C
C5 0.37694(18) 0.51749(16) 0.5279(5) 0.0250(6) Uani d 1 . . C
C20 0.66008(17) 0.20134(18) 0.5611(5) 0.0281(6) Uani d 1 . . C
C7 0.43560(17) 0.41391(15) 0.3281(5) 0.0238(6) Uani d 1 . . C
H7 0.4668 0.3959 0.2083 0.029 Uiso calc 1 . . H
C17 0.50621(15) 0.25574(15) 0.4780(4) 0.0212(5) Uani d 1 . . C
C4 0.34524(16) 0.46666(15) 0.6772(5) 0.0241(6) Uani d 1 . . C
H4 0.3143 0.485 0.7972 0.029 Uiso calc 1 . . H
C6 0.42307(18) 0.49102(16) 0.3519(5) 0.0262(6) Uani d 1 . . C
H6 0.4456 0.5258 0.2497 0.031 Uiso calc 1 . . H
C14 0.38270(18) -0.00207(16) 0.4610(5) 0.0288(6) Uani d 1 . . C
C22 0.55278(16) 0.28447(15) 0.6496(5) 0.0238(6) Uani d 1 . . C
H22 0.5311 0.3236 0.7391 0.029 Uiso calc 1 . . H
C13 0.34142(17) 0.04346(17) 0.3155(5) 0.0265(6) Uani d 1 . . C
H13 0.317 0.0231 0.1875 0.032 Uiso calc 1 . . H
C15 0.41810(19) 0.02594(17) 0.6464(5) 0.0311(7) Uani d 1 . . C
H15 0.4456 -0.0069 0.7448 0.037 Uiso calc 1 . . H
C21 0.62983(16) 0.25752(16) 0.6932(5) 0.0265(6) Uani d 1 . . C
H21 0.6607 0.2774 0.8112 0.032 Uiso calc 1 . . H
C16 0.41317(17) 0.10340(16) 0.6881(5) 0.0282(6) Uani d 1 . . C
H16 0.4385 0.1236 0.8151 0.034 Uiso calc 1 . . H
C3 0.32257(17) 0.33448(16) 0.8189(5) 0.0241(6) Uani d 1 . . C
H3A 0.264 0.329 0.7907 0.029 Uiso calc 1 . . H
H3B 0.3294 0.3559 0.9677 0.029 Uiso calc 1 . . H
C2 0.36228(17) 0.25690(16) 0.8089(4) 0.0233(6) Uani d 1 . . C
H2A 0.418 0.2599 0.8668 0.028 Uiso calc 1 . . H
H2B 0.3315 0.2202 0.899 0.028 Uiso calc 1 . . H
C10 0.3247(2) 0.62382(18) 0.7232(6) 0.0354(7) Uani d 1 . . C
H10A 0.3233 0.6794 0.7161 0.053 Uiso calc 1 . . H
H10B 0.3517 0.6079 0.8584 0.053 Uiso calc 1 . . H
H10C 0.2694 0.604 0.7217 0.053 Uiso calc 1 . . H
C12 0.33721(16) 0.11964(15) 0.3635(5) 0.0225(6) Uani d 1 . . C
C8 0.40322(16) 0.36187(15) 0.4769(4) 0.0214(5) Uani d 1 . . C
C1 0.41812(16) 0.27787(14) 0.4411(4) 0.0203(5) Uani d 1 . . C
H1 0.4047 0.2663 0.2849 0.024 Uiso calc 1 . . H
N1 0.36361(14) 0.23198(13) 0.5800(4) 0.0215(5) Uani d 1 . . N
O1 0.36772(13) 0.59494(11) 0.5392(4) 0.0307(5) Uani d 1 . . O
F3 0.49966(9) 0.17086(9) 0.1801(3) 0.0289(4) Uani d 1 . . F
F1 0.29748(10) 0.16511(9) 0.2233(3) 0.0290(4) Uani d 1 . . F
F2 0.38839(12) -0.07713(10) 0.4147(3) 0.0393(5) Uani d 1 . . F
F4 0.73537(10) 0.17432(11) 0.5994(3) 0.0394(5) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C19 H19 . 0.95 ?
C19 C18 . 1.381(4) ?
C19 C20 . 1.378(4) ?
C11 C16 . 1.391(4) ?
C11 C12 . 1.384(4) ?
C11 N1 . 1.428(3) ?
C18 C17 . 1.382(4) ?
C18 F3 . 1.358(3) ?
C9 C4 . 1.401(4) ?
C9 C3 . 1.504(4) ?
C9 C8 . 1.393(4) ?
C5 C4 . 1.381(4) ?
C5 C6 . 1.398(4) ?
C5 O1 . 1.373(3) ?
C20 C21 . 1.371(4) ?
C20 F4 . 1.355(3) ?
C7 H7 . 0.95 ?
C7 C6 . 1.380(4) ?
C7 C8 . 1.397(4) ?
C17 C22 . 1.396(4) ?
C17 C1 . 1.526(4) ?
C4 H4 . 0.95 ?
C6 H6 . 0.95 ?
C14 C13 . 1.378(4) ?
C14 C15 . 1.366(4) ?
C14 F2 . 1.354(3) ?
C22 H22 . 0.95 ?
C22 C21 . 1.387(4) ?
C13 H13 . 0.95 ?
C13 C12 . 1.374(4) ?
C15 H15 . 0.95 ?
C15 C16 . 1.389(4) ?
C21 H21 . 0.95 ?
C16 H16 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C2 . 1.516(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 N1 . 1.465(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.424(4) ?
C12 F1 . 1.344(3) ?
C8 C1 . 1.514(4) ?
C1 H1 . 1 ?
C1 N1 . 1.478(3) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C18 C19 H19 122.1 . . ?
C20 C19 H19 122.1 . . ?
C20 C19 C18 115.9(3) . . ?
C16 C11 N1 124.5(3) . . ?
C12 C11 C16 116.9(3) . . ?
C12 C11 N1 118.6(2) . . ?
C19 C18 C17 124.6(3) . . ?
F3 C18 C19 116.9(2) . . ?
F3 C18 C17 118.6(2) . . ?
C4 C9 C3 119.5(2) . . ?
C8 C9 C4 119.3(3) . . ?
C8 C9 C3 121.2(2) . . ?
C4 C5 C6 120.0(3) . . ?
O1 C5 C4 124.5(3) . . ?
O1 C5 C6 115.5(3) . . ?
C21 C20 C19 123.4(3) . . ?
F4 C20 C19 117.3(3) . . ?
F4 C20 C21 119.2(3) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C18 C17 C22 116.1(2) . . ?
C18 C17 C1 120.5(2) . . ?
C22 C17 C1 123.1(2) . . ?
C9 C4 H4 119.6 . . ?
C5 C4 C9 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C15 C14 C13 122.5(3) . . ?
F2 C14 C13 117.8(3) . . ?
F2 C14 C15 119.7(3) . . ?
C17 C22 H22 119 . . ?
C21 C22 C17 121.9(3) . . ?
C21 C22 H22 119 . . ?
C14 C13 H13 121.5 . . ?
C12 C13 C14 117.0(3) . . ?
C12 C13 H13 121.5 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(3) . . ?
C16 C15 H15 120.6 . . ?
C20 C21 C22 118.0(3) . . ?
C20 C21 H21 121 . . ?
C22 C21 H21 121 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C9 C3 C2 111.8(2) . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C3 C2 H2A 110 . . ?
C3 C2 H2B 110 . . ?
H2A C2 H2B 108.4 . . ?
N1 C2 C3 108.3(2) . . ?
N1 C2 H2A 110 . . ?
N1 C2 H2B 110 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C13 C12 C11 123.6(3) . . ?
F1 C12 C11 118.4(2) . . ?
F1 C12 C13 118.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 C1 121.8(2) . . ?
C7 C8 C1 118.9(2) . . ?
C17 C1 H1 107.5 . . ?
C8 C1 C17 112.5(2) . . ?
C8 C1 H1 107.5 . . ?
N1 C1 C17 111.1(2) . . ?
N1 C1 C8 110.5(2) . . ?
N1 C1 H1 107.5 . . ?
C11 N1 C2 115.4(2) . . ?
C11 N1 C1 113.6(2) . . ?
C2 N1 C1 113.1(2) . . ?
C5 O1 C10 116.7(2) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C19 C18 C17 C22 1.0(4) . . . . ?
C19 C18 C17 C1 -173.5(3) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C18 C19 C20 F4 -179.9(3) . . . . ?
C18 C17 C22 C21 -1.3(4) . . . . ?
C18 C17 C1 C8 -144.6(3) . . . . ?
C18 C17 C1 N1 90.8(3) . . . . ?
C9 C3 C2 N1 -49.5(3) . . . . ?
C9 C8 C1 C17 -110.9(3) . . . . ?
C9 C8 C1 N1 13.9(4) . . . . ?
C20 C19 C18 C17 0.2(4) . . . . ?
C20 C19 C18 F3 -179.8(2) . . . . ?
C7 C8 C1 C17 69.1(3) . . . . ?
C7 C8 C1 N1 -166.1(2) . . . . ?
C17 C22 C21 C20 0.4(4) . . . . ?
C17 C1 N1 C11 -57.0(3) . . . . ?
C17 C1 N1 C2 77.1(3) . . . . ?
C4 C9 C3 C2 -162.9(2) . . . . ?
C4 C9 C8 C7 1.0(4) . . . . ?
C4 C9 C8 C1 -179.0(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C4 C5 O1 C10 2.3(4) . . . . ?
C6 C5 C4 C9 -0.5(4) . . . . ?
C6 C5 O1 C10 -176.7(3) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 C1 179.3(3) . . . . ?
C14 C13 C12 C11 0.1(4) . . . . ?
C14 C13 C12 F1 179.8(2) . . . . ?
C14 C15 C16 C11 1.2(4) . . . . ?
C22 C17 C1 C8 41.3(3) . . . . ?
C22 C17 C1 N1 -83.3(3) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C15 C14 C13 C12 0.2(4) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C16 C11 C12 F1 -179.4(2) . . . . ?
C16 C11 N1 C2 -30.5(4) . . . . ?
C16 C11 N1 C1 102.4(3) . . . . ?
C3 C9 C4 C5 -179.7(3) . . . . ?
C3 C9 C8 C7 -179.7(2) . . . . ?
C3 C9 C8 C1 0.3(4) . . . . ?
C3 C2 N1 C11 -158.8(2) . . . . ?
C3 C2 N1 C1 68.0(3) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C12 C11 N1 C2 149.8(2) . . . . ?
C12 C11 N1 C1 -77.2(3) . . . . ?
C8 C9 C4 C5 -0.4(4) . . . . ?
C8 C9 C3 C2 17.8(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?
C8 C1 N1 C11 177.4(2) . . . . ?
C8 C1 N1 C2 -48.5(3) . . . . ?
C1 C17 C22 C21 173.1(3) . . . . ?
N1 C11 C16 C15 179.5(3) . . . . ?
N1 C11 C12 C13 179.9(3) . . . . ?
N1 C11 C12 F1 0.2(4) . . . . ?
O1 C5 C4 C9 -179.5(3) . . . . ?
O1 C5 C6 C7 179.8(3) . . . . ?
F3 C18 C17 C22 -179.0(2) . . . . ?
F3 C18 C17 C1 6.5(4) . . . . ?
F2 C14 C13 C12 -179.1(2) . . . . ?
F2 C14 C15 C16 178.5(3) . . . . ?
F4 C20 C21 C22 179.6(3) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

data_6-9
_database_code_depnum_ccdc_archive 'CCDC 1540736'
 
_audit_creation_date                    2020-03-09T09:07:24-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          9.445(6)
_cell_length_b                          21.293(11)
_cell_length_c                          9.590(6)
_cell_angle_alpha                       90
_cell_angle_beta                        112.96(2)
_cell_angle_gamma                       90
_cell_volume                            1775.9(18)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4135
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              plate
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.01
_exptl_crystal_density_diffrn           1.449
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.79
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   9543
_diffrn_reflns_av_R_equivalents         0.0617
_diffrn_reflns_theta_min                3.024
_diffrn_reflns_theta_max                25.026
_diffrn_reflns_theta_full               25.026
_diffrn_measured_fraction_theta_max
                                        0.989
_diffrn_measured_fraction_theta_full
                                        0.989
_diffrn_reflns_Laue_measured_fraction_full
                                        0.989
_diffrn_reflns_Laue_measured_fraction_max
                                        0.989
_diffrn_reflns_point_group_measured_fraction_full
                                        0.989
_diffrn_reflns_point_group_measured_fraction_max
                                        0.989
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min              -25
_diffrn_reflns_limit_k_max              25
_diffrn_reflns_limit_l_min              -11
_diffrn_reflns_limit_l_max              10
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3113
_reflns_number_gt                       2419
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0848
_refine_ls_R_factor_gt                  0.0717
_refine_ls_wR_factor_ref                0.2162
_refine_ls_goodness_of_fit_ref          1.08
_refine_ls_restrained_S_all             1.08
_refine_ls_number_reflns                3113
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.1384P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.604
_refine_diff_density_min                -0.36
_refine_diff_density_rms                0.079
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C19 0.2389(3) 0.72638(11) 0.3398(3) 0.0299(6) Uani d 1 . . C
H19 0.2806 0.7533 0.2864 0.036 Uiso calc 1 . . H
C18 0.3151(3) 0.67234(12) 0.4077(3) 0.0273(6) Uani d 1 . . C
C1 0.3425(3) 0.56909(11) 0.5492(3) 0.0270(6) Uani d 1 . . C
H1 0.4531 0.5732 0.5647 0.032 Uiso calc 1 . . H
C22 0.1219(3) 0.64534(11) 0.4955(3) 0.0291(6) Uani d 1 . . C
H22 0.0794 0.6182 0.5477 0.035 Uiso calc 1 . . H
C5 0.1580(3) 0.41691(12) 0.2322(3) 0.0306(6) Uani d 1 . . C
C20 0.1007(3) 0.74069(12) 0.3508(3) 0.0326(6) Uani d 1 . . C
H20 0.045 0.7775 0.3054 0.039 Uiso calc 1 . . H
C7 0.2454(3) 0.52290(12) 0.2881(3) 0.0294(6) Uani d 1 . . C
H7 0.2672 0.5624 0.2549 0.035 Uiso calc 1 . . H
C21 0.0466(3) 0.69961(12) 0.4298(3) 0.0328(6) Uani d 1 . . C
C9 0.2384(3) 0.45655(12) 0.4871(3) 0.0293(6) Uani d 1 . . C
C16 0.5197(3) 0.64586(12) 0.8027(3) 0.0309(6) Uani d 1 . . C
H16 0.5483 0.6444 0.7182 0.037 Uiso calc 1 . . H
C6 0.1882(3) 0.47471(12) 0.1832(3) 0.0312(6) Uani d 1 . . C
H6 0.17 0.4813 0.0796 0.037 Uiso calc 1 . . H
C2 0.3783(3) 0.49289(12) 0.7516(3) 0.0314(6) Uani d 1 . . C
H2A 0.3847 0.4888 0.8567 0.038 Uiso calc 1 . . H
H2B 0.4807 0.4832 0.7513 0.038 Uiso calc 1 . . H
C4 0.1858(3) 0.40822(12) 0.3837(3) 0.0318(6) Uani d 1 . . C
H4 0.1682 0.3681 0.4173 0.038 Uiso calc 1 . . H
C3 0.2608(3) 0.44734(12) 0.6501(3) 0.0345(6) Uani d 1 . . C
H3A 0.2954 0.4038 0.6815 0.041 Uiso calc 1 . . H
H3B 0.1617 0.4537 0.6607 0.041 Uiso calc 1 . . H
C15 0.5895(3) 0.68986(13) 0.9158(3) 0.0356(7) Uani d 1 . . C
H15 0.6631 0.7188 0.9087 0.043 Uiso calc 1 . . H
C12 0.3715(3) 0.60883(13) 0.9355(3) 0.0360(7) Uani d 1 . . C
C13 0.4400(4) 0.65073(14) 1.0511(3) 0.0411(7) Uani d 1 . . C
H13 0.4132 0.6523 1.1367 0.049 Uiso calc 1 . . H
C14 0.5482(3) 0.68998(14) 1.0382(3) 0.0396(7) Uani d 1 . . C
C10 0.0588(4) 0.37515(14) -0.0185(3) 0.0444(8) Uani d 1 . . C
H10A 0.0229 0.3353 -0.0718 0.067 Uiso calc 1 . . H
H10B 0.1465 0.3906 -0.0389 0.067 Uiso calc 1 . . H
H10C -0.0246 0.4061 -0.0539 0.067 Uiso calc 1 . . H
C17 0.2605(3) 0.63054(11) 0.4850(3) 0.0263(6) Uani d 1 . . C
C11 0.4096(3) 0.60381(12) 0.8088(3) 0.0285(6) Uani d 1 . . C
C8 0.2717(3) 0.51507(12) 0.4398(3) 0.0283(6) Uani d 1 . . C
N1 0.3335(2) 0.55777(9) 0.6968(2) 0.0272(5) Uani d 1 . . N
O1 0.1045(2) 0.36568(9) 0.1400(2) 0.0363(5) Uani d 1 . . O
F3 0.45171(17) 0.65968(7) 0.39668(17) 0.0336(4) Uani d 1 . . F
F4 -0.08722(18) 0.71384(7) 0.4449(2) 0.0442(5) Uani d 1 . . F
F1 0.26065(19) 0.57040(8) 0.94415(18) 0.0446(5) Uani d 1 . . F
F2 0.6162(2) 0.73273(9) 1.15037(19) 0.0563(6) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C19 H19 . 0.95 ?
C19 C18 . 1.378(4) ?
C19 C20 . 1.384(4) ?
C18 C17 . 1.380(4) ?
C18 F3 . 1.362(3) ?
C1 H1 . 1 ?
C1 C17 . 1.523(3) ?
C1 C8 . 1.524(3) ?
C1 N1 . 1.471(3) ?
C22 H22 . 0.95 ?
C22 C21 . 1.374(4) ?
C22 C17 . 1.388(4) ?
C5 C6 . 1.386(4) ?
C5 C4 . 1.385(4) ?
C5 O1 . 1.371(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.380(4) ?
C7 H7 . 0.95 ?
C7 C6 . 1.391(4) ?
C7 C8 . 1.387(4) ?
C21 F4 . 1.362(3) ?
C9 C4 . 1.380(4) ?
C9 C3 . 1.507(4) ?
C9 C8 . 1.403(4) ?
C16 H16 . 0.95 ?
C16 C15 . 1.389(4) ?
C16 C11 . 1.391(4) ?
C6 H6 . 0.95 ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.509(4) ?
C2 N1 . 1.480(3) ?
C4 H4 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C15 H15 . 0.95 ?
C15 C14 . 1.374(4) ?
C12 C13 . 1.373(4) ?
C12 C11 . 1.399(4) ?
C12 F1 . 1.356(3) ?
C13 H13 . 0.95 ?
C13 C14 . 1.362(5) ?
C14 F2 . 1.364(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.423(4) ?
C11 N1 . 1.424(3) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C19 C18 C17 123.8(2) . . ?
F3 C18 C19 117.6(2) . . ?
F3 C18 C17 118.5(2) . . ?
C17 C1 H1 108.7 . . ?
C17 C1 C8 110.7(2) . . ?
C8 C1 H1 108.7 . . ?
N1 C1 H1 108.7 . . ?
N1 C1 C17 108.59(19) . . ?
N1 C1 C8 111.4(2) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C17 119.4(2) . . ?
C17 C22 H22 120.3 . . ?
C4 C5 C6 119.7(2) . . ?
O1 C5 C6 124.1(2) . . ?
O1 C5 C4 116.2(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.7(2) . . ?
C21 C20 H20 121.1 . . ?
C6 C7 H7 119 . . ?
C8 C7 H7 119 . . ?
C8 C7 C6 122.0(2) . . ?
C22 C21 C20 123.3(3) . . ?
F4 C21 C22 118.3(2) . . ?
F4 C21 C20 118.4(2) . . ?
C4 C9 C3 120.9(2) . . ?
C4 C9 C8 119.6(2) . . ?
C8 C9 C3 119.5(2) . . ?
C15 C16 H16 118.8 . . ?
C15 C16 C11 122.4(2) . . ?
C11 C16 H16 118.8 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.6(2) . . ?
C5 C4 H4 119.3 . . ?
C9 C4 C5 121.5(2) . . ?
C9 C4 H4 119.3 . . ?
C9 C3 C2 110.8(2) . . ?
C9 C3 H3A 109.5 . . ?
C9 C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C16 C15 H15 121.3 . . ?
C14 C15 C16 117.5(3) . . ?
C14 C15 H15 121.3 . . ?
C13 C12 C11 123.4(3) . . ?
F1 C12 C13 118.3(2) . . ?
F1 C12 C11 118.3(2) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 C15 123.3(3) . . ?
C13 C14 F2 118.5(3) . . ?
F2 C14 C15 118.2(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C18 C17 C1 122.3(2) . . ?
C18 C17 C22 116.9(2) . . ?
C22 C17 C1 120.7(2) . . ?
C16 C11 C12 115.9(2) . . ?
C16 C11 N1 125.2(2) . . ?
C12 C11 N1 118.8(2) . . ?
C7 C8 C1 118.8(2) . . ?
C7 C8 C9 118.3(2) . . ?
C9 C8 C1 122.7(2) . . ?
C1 N1 C2 112.24(19) . . ?
C11 N1 C1 114.3(2) . . ?
C11 N1 C2 112.6(2) . . ?
C5 O1 C10 117.3(2) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C19 C18 C17 C1 175.7(2) . . . . ?
C19 C18 C17 C22 -1.1(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 F4 178.4(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C20 C19 C18 C17 1.0(4) . . . . ?
C20 C19 C18 F3 -179.3(2) . . . . ?
C21 C22 C17 C18 0.1(4) . . . . ?
C21 C22 C17 C1 -176.7(2) . . . . ?
C16 C15 C14 C13 -2.0(4) . . . . ?
C16 C15 C14 F2 179.7(2) . . . . ?
C16 C11 N1 C1 -18.0(3) . . . . ?
C16 C11 N1 C2 111.7(3) . . . . ?
C6 C5 C4 C9 2.1(4) . . . . ?
C6 C5 O1 C10 -8.4(4) . . . . ?
C6 C7 C8 C1 176.8(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C4 C5 O1 C10 173.1(2) . . . . ?
C4 C9 C3 C2 155.2(2) . . . . ?
C4 C9 C8 C1 -174.9(2) . . . . ?
C4 C9 C8 C7 2.1(4) . . . . ?
C3 C9 C4 C5 177.0(2) . . . . ?
C3 C9 C8 C1 5.0(4) . . . . ?
C3 C9 C8 C7 -177.9(2) . . . . ?
C3 C2 N1 C1 -67.2(3) . . . . ?
C3 C2 N1 C11 162.1(2) . . . . ?
C15 C16 C11 C12 0.7(4) . . . . ?
C15 C16 C11 N1 179.8(2) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C12 C13 C14 F2 179.0(2) . . . . ?
C12 C11 N1 C1 161.2(2) . . . . ?
C12 C11 N1 C2 -69.2(3) . . . . ?
C13 C12 C11 C16 -2.1(4) . . . . ?
C13 C12 C11 N1 178.7(2) . . . . ?
C17 C1 C8 C7 47.6(3) . . . . ?
C17 C1 C8 C9 -135.4(2) . . . . ?
C17 C1 N1 C2 167.02(19) . . . . ?
C17 C1 N1 C11 -63.1(3) . . . . ?
C17 C22 C21 C20 0.9(4) . . . . ?
C17 C22 C21 F4 -178.4(2) . . . . ?
C11 C16 C15 C14 1.3(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C8 C1 C17 C18 -96.1(3) . . . . ?
C8 C1 C17 C22 80.6(3) . . . . ?
C8 C1 N1 C2 44.9(3) . . . . ?
C8 C1 N1 C11 174.77(19) . . . . ?
C8 C7 C6 C5 -0.7(4) . . . . ?
C8 C9 C4 C5 -3.1(4) . . . . ?
C8 C9 C3 C2 -24.7(3) . . . . ?
N1 C1 C17 C18 141.4(2) . . . . ?
N1 C1 C17 C22 -42.0(3) . . . . ?
N1 C1 C8 C7 168.5(2) . . . . ?
N1 C1 C8 C9 -14.5(3) . . . . ?
N1 C2 C3 C9 54.3(3) . . . . ?
O1 C5 C6 C7 -178.6(2) . . . . ?
O1 C5 C4 C9 -179.4(2) . . . . ?
F3 C18 C17 C1 -4.0(3) . . . . ?
F3 C18 C17 C22 179.2(2) . . . . ?
F1 C12 C13 C14 -178.3(2) . . . . ?
F1 C12 C11 C16 177.7(2) . . . . ?
F1 C12 C11 N1 -1.5(4) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-13
_database_code_depnum_ccdc_archive 'CCDC 1540718'
 
_audit_creation_date                    2020-03-09T09:08:17-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'C 1 2/c 1'
_symmetry_space_group_name_Hall         '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                          36.079(4)
_cell_length_b                          6.2372(6)
_cell_length_c                          16.051(2)
_cell_angle_alpha                       90
_cell_angle_beta                        104.627(6)
_cell_angle_gamma                       90
_cell_volume                            3495.0(7)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           4840
_cell_measurement_theta_min             3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              irregular
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.25
_exptl_crystal_size_mid                 0.19
_exptl_crystal_size_min                 0.18
_exptl_crystal_density_diffrn           1.472
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1600
_exptl_absorpt_coefficient_mu           0.119
_exptl_absorpt_correction_type          Multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.878
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   11954
_diffrn_reflns_av_R_equivalents         0.0765
_diffrn_reflns_theta_min                3.039
_diffrn_reflns_theta_max                27.493
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.991
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.991
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.991
_diffrn_reflns_limit_h_min              -45
_diffrn_reflns_limit_h_max              46
_diffrn_reflns_limit_k_min              -8
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min              -20
_diffrn_reflns_limit_l_max              20
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3975
_reflns_number_gt                       3509
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0477
_refine_ls_R_factor_gt                  0.0431
_refine_ls_wR_factor_ref                0.1145
_refine_ls_goodness_of_fit_ref          1.045
_refine_ls_restrained_S_all             1.045
_refine_ls_number_reflns                3975
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0423P)²+3.0682P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.252
_refine_diff_density_min                -0.265
_refine_diff_density_rms                0.056
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.40659(2) 0.96899(12) 0.60233(5) 0.02346(19) Uani d 1 . . F
F2 0.49708(2) 0.29704(14) 0.57062(6) 0.0289(2) Uani d 1 . . F
F3 0.41588(2) 1.02214(13) 0.41797(5) 0.0261(2) Uani d 1 . . F
F4 0.45258(2) 0.95718(14) 0.29622(5) 0.0283(2) Uani d 1 . . F
O1 0.19366(3) 0.71075(15) 0.31545(6) 0.0226(2) Uani d 1 . . O
N1 0.37123(3) 0.61245(16) 0.51699(6) 0.0163(2) Uani d 1 . . N
C1 0.35526(3) 0.7614(2) 0.44466(7) 0.0163(2) Uani d 1 . . C
H1 0.3614 0.9105 0.4667 0.02 Uiso calc 1 . . H
C2 0.35482(4) 0.3968(2) 0.50391(8) 0.0184(3) Uani d 1 . . C
H2A 0.3684 0.3009 0.5509 0.022 Uiso calc 1 . . H
H2B 0.3577 0.3377 0.4486 0.022 Uiso calc 1 . . H
C3 0.31268(4) 0.4096(2) 0.50305(8) 0.0195(3) Uani d 1 . . C
H3A 0.3006 0.268 0.4869 0.023 Uiso calc 1 . . H
H3B 0.3103 0.4449 0.5616 0.023 Uiso calc 1 . . H
C4 0.25203(4) 0.5632(2) 0.40895(8) 0.0184(3) Uani d 1 . . C
H4 0.2384 0.449 0.4269 0.022 Uiso calc 1 . . H
C5 0.23236(4) 0.7157(2) 0.35167(8) 0.0186(3) Uani d 1 . . C
C6 0.25224(4) 0.8863(2) 0.32677(8) 0.0206(3) Uani d 1 . . C
H6 0.2389 0.9931 0.2886 0.025 Uiso calc 1 . . H
C7 0.29156(4) 0.8982(2) 0.35813(8) 0.0194(3) Uani d 1 . . C
H7 0.3051 1.0136 0.3407 0.023 Uiso calc 1 . . H
C8 0.31198(3) 0.7440(2) 0.41502(8) 0.0169(2) Uani d 1 . . C
C9 0.29191(4) 0.5766(2) 0.44053(8) 0.0175(3) Uani d 1 . . C
C10 0.17291(4) 0.5354(2) 0.33851(9) 0.0245(3) Uani d 1 . . C
H10A 0.1461 0.5435 0.3057 0.037 Uiso calc 1 . . H
H10B 0.1743 0.542 0.4002 0.037 Uiso calc 1 . . H
H10C 0.1841 0.4002 0.3254 0.037 Uiso calc 1 . . H
C11 0.41173(4) 0.6206(2) 0.54818(8) 0.0167(2) Uani d 1 . . C
C12 0.42922(4) 0.8014(2) 0.59277(8) 0.0190(3) Uani d 1 . . C
C13 0.46804(4) 0.8173(2) 0.62809(8) 0.0230(3) Uani d 1 . . C
H13 0.4786 0.945 0.6567 0.028 Uiso calc 1 . . H
C14 0.49164(4) 0.6453(2) 0.62164(9) 0.0236(3) Uani d 1 . . C
H14 0.5185 0.6509 0.6465 0.028 Uiso calc 1 . . H
C15 0.47472(4) 0.4669(2) 0.57801(9) 0.0213(3) Uani d 1 . . C
C16 0.43579(4) 0.4508(2) 0.54050(8) 0.0189(3) Uani d 1 . . C
H16 0.4256 0.325 0.5098 0.023 Uiso calc 1 . . H
C17 0.37407(3) 0.7286(2) 0.37002(7) 0.0164(2) Uani d 1 . . C
C18 0.40455(4) 0.8567(2) 0.36345(8) 0.0182(3) Uani d 1 . . C
C19 0.42391(4) 0.8227(2) 0.30045(8) 0.0201(3) Uani d 1 . . C
C20 0.41389(4) 0.6577(2) 0.24259(8) 0.0223(3) Uani d 1 . . C
H20 0.4278 0.6314 0.2007 0.027 Uiso calc 1 . . H
C21 0.38285(4) 0.5299(2) 0.24660(8) 0.0223(3) Uani d 1 . . C
H21 0.3751 0.4168 0.2063 0.027 Uiso calc 1 . . H
C22 0.36300(4) 0.5657(2) 0.30887(8) 0.0193(3) Uani d 1 . . C
H22 0.3416 0.4784 0.31 0.023 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C12 . 1.3589(15) ?
F2 C15 . 1.3545(15) ?
F3 C18 . 1.3478(14) ?
F4 C19 . 1.3467(14) ?
O1 C5 . 1.3706(15) ?
O1 C10 . 1.4259(16) ?
N1 C1 . 1.4848(15) ?
N1 C2 . 1.4635(16) ?
N1 C11 . 1.4209(16) ?
C1 H1 . 1 ?
C1 C8 . 1.5172(17) ?
C1 C17 . 1.5324(16) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.5189(17) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.5082(17) ?
C4 H4 . 0.95 ?
C4 C5 . 1.3875(18) ?
C4 C9 . 1.4020(18) ?
C5 C6 . 1.3966(18) ?
C6 H6 . 0.95 ?
C6 C7 . 1.3825(18) ?
C7 H7 . 0.95 ?
C7 C8 . 1.4007(17) ?
C8 C9 . 1.3896(17) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.3976(18) ?
C11 C16 . 1.3947(18) ?
C12 C13 . 1.3755(18) ?
C13 H13 . 0.95 ?
C13 C14 . 1.3897(19) ?
C14 H14 . 0.95 ?
C14 C15 . 1.373(2) ?
C15 C16 . 1.3850(19) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3847(17) ?
C17 C22 . 1.3990(17) ?
C18 C19 . 1.3828(18) ?
C19 C20 . 1.3722(19) ?
C20 H20 . 0.95 ?
C20 C21 . 1.3892(19) ?
C21 H21 . 0.95 ?
C21 C22 . 1.3868(18) ?
C22 H22 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.91(10) . . ?
C2 N1 C1 113.57(10) . . ?
C11 N1 C1 114.49(9) . . ?
C11 N1 C2 115.24(10) . . ?
N1 C1 H1 107.3 . . ?
N1 C1 C8 111.46(10) . . ?
N1 C1 C17 111.53(10) . . ?
C8 C1 H1 107.3 . . ?
C8 C1 C17 111.68(10) . . ?
C17 C1 H1 107.3 . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 C3 108.71(10) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C9 C3 C2 111.74(10) . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C9 120.33(12) . . ?
C9 C4 H4 119.8 . . ?
O1 C5 C4 124.16(12) . . ?
O1 C5 C6 115.96(11) . . ?
C4 C5 C6 119.88(12) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.40(12) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.51(12) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C1 119.04(11) . . ?
C9 C8 C1 122.21(11) . . ?
C9 C8 C7 118.72(12) . . ?
C4 C9 C3 119.42(11) . . ?
C8 C9 C3 120.44(11) . . ?
C8 C9 C4 120.13(12) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 120.04(11) . . ?
C16 C11 N1 123.32(11) . . ?
C16 C11 C12 116.57(12) . . ?
F1 C12 C11 118.16(11) . . ?
F1 C12 C13 118.43(11) . . ?
C13 C12 C11 123.40(12) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.52(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.51(12) . . ?
C15 C14 H14 121.2 . . ?
F2 C15 C14 118.72(12) . . ?
F2 C15 C16 117.79(12) . . ?
C14 C15 C16 123.49(12) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.48(12) . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C1 119.98(11) . . ?
C18 C17 C22 117.20(11) . . ?
C22 C17 C1 122.75(11) . . ?
F3 C18 C17 120.57(11) . . ?
F3 C18 C19 117.78(11) . . ?
C19 C18 C17 121.64(12) . . ?
F4 C19 C18 118.51(12) . . ?
F4 C19 C20 120.51(11) . . ?
C20 C19 C18 120.98(12) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.47(12) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.66(12) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 120.99(12) . . ?
C21 C22 H22 119.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C12 C13 C14 177.89(11) . . . . ?
F2 C15 C16 C11 178.74(11) . . . . ?
F3 C18 C19 F4 -0.79(18) . . . . ?
F3 C18 C19 C20 -179.83(12) . . . . ?
F4 C19 C20 C21 -176.67(12) . . . . ?
O1 C5 C6 C7 -177.71(11) . . . . ?
N1 C1 C8 C7 168.77(10) . . . . ?
N1 C1 C8 C9 -13.06(16) . . . . ?
N1 C1 C17 C18 -95.58(13) . . . . ?
N1 C1 C17 C22 81.28(14) . . . . ?
N1 C2 C3 C9 51.85(14) . . . . ?
N1 C11 C12 F1 -2.27(17) . . . . ?
N1 C11 C12 C13 177.08(11) . . . . ?
N1 C11 C16 C15 -175.53(11) . . . . ?
C1 N1 C2 C3 -65.64(13) . . . . ?
C1 N1 C11 C12 69.51(14) . . . . ?
C1 N1 C11 C16 -113.70(13) . . . . ?
C1 C8 C9 C3 3.02(18) . . . . ?
C1 C8 C9 C4 -177.67(11) . . . . ?
C1 C17 C18 F3 -5.58(18) . . . . ?
C1 C17 C18 C19 175.56(11) . . . . ?
C1 C17 C22 C21 -174.48(12) . . . . ?
C2 N1 C1 C8 44.91(13) . . . . ?
C2 N1 C1 C17 -80.66(12) . . . . ?
C2 N1 C11 C12 -156.04(11) . . . . ?
C2 N1 C11 C16 20.76(16) . . . . ?
C2 C3 C9 C4 158.27(11) . . . . ?
C2 C3 C9 C8 -22.42(16) . . . . ?
C4 C5 C6 C7 1.49(19) . . . . ?
C5 C4 C9 C3 179.73(11) . . . . ?
C5 C4 C9 C8 0.42(18) . . . . ?
C5 C6 C7 C8 -0.57(19) . . . . ?
C6 C7 C8 C1 177.81(11) . . . . ?
C6 C7 C8 C9 -0.43(18) . . . . ?
C7 C8 C9 C3 -178.80(11) . . . . ?
C7 C8 C9 C4 0.50(18) . . . . ?
C8 C1 C17 C18 138.96(12) . . . . ?
C8 C1 C17 C22 -44.17(16) . . . . ?
C9 C4 C5 O1 177.70(11) . . . . ?
C9 C4 C5 C6 -1.43(18) . . . . ?
C10 O1 C5 C4 -0.49(18) . . . . ?
C10 O1 C5 C6 178.67(11) . . . . ?
C11 N1 C1 C8 -179.87(10) . . . . ?
C11 N1 C1 C17 54.55(13) . . . . ?
C11 N1 C2 C3 159.49(10) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C12 C11 C16 C15 1.37(17) . . . . ?
C12 C13 C14 C15 1.31(19) . . . . ?
C13 C14 C15 F2 179.88(11) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C11 -1.53(19) . . . . ?
C16 C11 C12 F1 -179.27(10) . . . . ?
C16 C11 C12 C13 0.07(18) . . . . ?
C17 C1 C8 C7 -65.74(14) . . . . ?
C17 C1 C8 C9 112.43(13) . . . . ?
C17 C18 C19 F4 178.10(11) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C17 C22 C21 2.47(19) . . . . ?
C18 C19 C20 C21 2.4(2) . . . . ?
C19 C20 C21 C22 -1.3(2) . . . . ?
C20 C21 C22 C17 -1.1(2) . . . . ?
C22 C17 C18 F3 177.39(11) . . . . ?
C22 C17 C18 C19 -1.48(19) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-16
_database_code_depnum_ccdc_archive 'CCDC 1540719'
 
_audit_creation_date                    2020-03-09T09:09:14-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
_chemical_absolute_configuration        unk
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 c 1'
_symmetry_space_group_name_Hall         'P -2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x, -y, z+1/2'

_cell_length_a                          17.468(3)
_cell_length_b                          6.2025(10)
_cell_length_c                          16.338(3)
_cell_angle_alpha                       90
_cell_angle_beta                        92.208(9)
_cell_angle_gamma                       90
_cell_volume                            1768.9(5)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4231
_cell_measurement_theta_min             3.3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              irregular
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           1.455
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.838
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   9932
_diffrn_reflns_av_R_equivalents         0.0468
_diffrn_reflns_theta_min                3.284
_diffrn_reflns_theta_max                25.026
_diffrn_reflns_theta_full               25.026
_diffrn_measured_fraction_theta_max
                                        0.995
_diffrn_measured_fraction_theta_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_max
                                        0.995
_diffrn_reflns_point_group_measured_fraction_full
                                        0.859
_diffrn_reflns_point_group_measured_fraction_max
                                        0.859
_diffrn_reflns_limit_h_min              -20
_diffrn_reflns_limit_h_max              20
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -15
_diffrn_reflns_limit_l_max              19
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    5388
_reflns_number_gt                       4164
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.104
_refine_ls_R_factor_gt                  0.087
_refine_ls_wR_factor_ref                0.235
_refine_ls_goodness_of_fit_ref          1.044
_refine_ls_restrained_S_all             1.044
_refine_ls_number_reflns                5388
_refine_ls_number_parameters            507
_refine_ls_number_restraints            2
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1622P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                1.085
_refine_diff_density_min                -0.338
_refine_diff_density_rms                0.112
_refine_ls_extinction_method            none
_refine_ls_abs_structure_details
;
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          -0.3(7)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.1790(3) 0.9720(7) 0.5473(3) 0.0281(11) Uani d 1 . . F
F2 0.0145(3) 0.2635(8) 0.4532(4) 0.0437(14) Uani d 1 . . F
F3 0.3328(3) 0.4609(8) 0.3023(3) 0.0301(11) Uani d 1 . . F
F4 0.1625(3) 1.0192(7) 0.3549(3) 0.0293(11) Uani d 1 . . F
O1 0.6100(3) 0.8255(9) 0.4345(4) 0.0283(13) Uani d 1 . . O
N1 0.2576(4) 0.6249(10) 0.4834(4) 0.0266(15) Uani d 1 . . N
C1 0.2846(4) 0.7763(12) 0.4208(5) 0.0220(16) Uani d 1 . . C
H1 0.2674 0.9228 0.4379 0.026 Uiso calc 1 . . H
C2 0.2954(5) 0.4129(14) 0.4837(5) 0.0288(18) Uani d 1 . . C
H2A 0.2915 0.3477 0.4284 0.035 Uiso calc 1 . . H
H2B 0.271 0.3145 0.5226 0.035 Uiso calc 1 . . H
C3 0.3791(4) 0.4502(14) 0.5097(5) 0.0277(18) Uani d 1 . . C
H3A 0.3824 0.4847 0.5689 0.033 Uiso calc 1 . . H
H3B 0.4081 0.3152 0.5015 0.033 Uiso calc 1 . . H
C4 0.4962(5) 0.6459(12) 0.4645(5) 0.0252(17) Uani d 1 . . C
H4 0.5269 0.5373 0.4904 0.03 Uiso calc 1 . . H
C5 0.5310(5) 0.8232(12) 0.4277(5) 0.0243(17) Uani d 1 . . C
C6 0.4869(4) 0.9807(11) 0.3867(5) 0.0187(16) Uani d 1 . . C
H6 0.511 1.0994 0.3614 0.022 Uiso calc 1 . . H
C7 0.4068(4) 0.9614(13) 0.3834(5) 0.0219(16) Uani d 1 . . C
H7 0.3761 1.0661 0.3551 0.026 Uiso calc 1 . . H
C8 0.3716(4) 0.7837(12) 0.4228(5) 0.0220(16) Uani d 1 . . C
C9 0.4162(4) 0.6294(12) 0.4631(5) 0.0222(16) Uani d 1 . . C
C10 0.6475(5) 1.0049(12) 0.4031(6) 0.0261(18) Uani d 1 . . C
H10A 0.6402 1.0074 0.3433 0.039 Uiso calc 1 . . H
H10B 0.7023 0.9963 0.4178 0.039 Uiso calc 1 . . H
H10C 0.6262 1.1368 0.4261 0.039 Uiso calc 1 . . H
C11 0.1766(4) 0.6179(12) 0.4891(5) 0.0233(16) Uani d 1 . . C
C12 0.1371(4) 0.7876(12) 0.5236(5) 0.0221(17) Uani d 1 . . C
C13 0.0604(5) 0.7845(15) 0.5359(6) 0.036(2) Uani d 1 . . C
H13 0.0364 0.9056 0.5597 0.043 Uiso calc 1 . . H
C14 0.0178(5) 0.6060(15) 0.5140(6) 0.034(2) Uani d 1 . . C
H14 -0.0354 0.5985 0.5235 0.041 Uiso calc 1 . . H
C15 0.0549(5) 0.4409(14) 0.4784(6) 0.031(2) Uani d 1 . . C
C16 0.1330(4) 0.4433(14) 0.4643(5) 0.0270(18) Uani d 1 . . C
H16 0.1561 0.3249 0.4378 0.032 Uiso calc 1 . . H
C17 0.2495(5) 0.7393(13) 0.3357(5) 0.0256(17) Uani d 1 . . C
C18 0.1878(4) 0.8650(12) 0.3062(5) 0.0256(17) Uani d 1 . . C
C19 0.1501(5) 0.8393(13) 0.2319(5) 0.0288(19) Uani d 1 . . C
H19 0.1093 0.9328 0.2152 0.035 Uiso calc 1 . . H
C20 0.1729(5) 0.6733(14) 0.1818(6) 0.0322(19) Uani d 1 . . C
H20 0.1468 0.6504 0.1304 0.039 Uiso calc 1 . . H
C21 0.2349(5) 0.5369(13) 0.2063(5) 0.0260(18) Uani d 1 . . C
H21 0.2506 0.4211 0.1728 0.031 Uiso calc 1 . . H
C22 0.2707(5) 0.5798(13) 0.2801(5) 0.0281(18) Uani d 1 . . C
F5 0.8237(3) 0.0267(8) 0.8186(3) 0.0340(12) Uani d 1 . . F
F6 0.9853(3) 0.7391(8) 0.7345(4) 0.0464(15) Uani d 1 . . F
F7 0.8384(3) -0.0158(7) 0.6273(3) 0.0269(11) Uani d 1 . . F
F8 0.6640(3) 0.5371(8) 0.5672(3) 0.0336(12) Uani d 1 . . F
O2 0.3905(3) 0.1641(9) 0.6812(4) 0.0302(14) Uani d 1 . . O
N2 0.7426(4) 0.3708(11) 0.7513(4) 0.0251(15) Uani d 1 . . N
C23 0.7148(4) 0.2201(11) 0.6870(5) 0.0240(17) Uani d 1 . . C
H23 0.7332 0.0739 0.7045 0.029 Uiso calc 1 . . H
C24 0.7065(5) 0.5832(13) 0.7494(5) 0.0307(19) Uani d 1 . . C
H24A 0.7102 0.6502 0.6947 0.037 Uiso calc 1 . . H
H24B 0.7311 0.6795 0.7909 0.037 Uiso calc 1 . . H
C25 0.6208(5) 0.5416(14) 0.7692(5) 0.0301(19) Uani d 1 . . C
H25A 0.6179 0.5098 0.8284 0.036 Uiso calc 1 . . H
H25B 0.5913 0.6753 0.758 0.036 Uiso calc 1 . . H
C26 0.5040(5) 0.3368(13) 0.7181(5) 0.0276(18) Uani d 1 . . C
H26 0.4735 0.4407 0.7445 0.033 Uiso calc 1 . . H
C27 0.4689(4) 0.1683(13) 0.6778(5) 0.0256(18) Uani d 1 . . C
C28 0.5126(5) 0.0142(12) 0.6367(5) 0.0238(18) Uani d 1 . . C
H28 0.4887 -0.1016 0.6075 0.029 Uiso calc 1 . . H
C29 0.5924(4) 0.0375(13) 0.6403(5) 0.0238(17) Uani d 1 . . C
H29 0.6231 -0.0641 0.6131 0.029 Uiso calc 1 . . H
C30 0.6278(5) 0.2086(13) 0.6837(5) 0.0263(18) Uani d 1 . . C
C31 0.5834(5) 0.3601(12) 0.7216(5) 0.0268(18) Uani d 1 . . C
C32 0.3535(5) -0.0205(12) 0.6444(6) 0.0269(18) Uani d 1 . . C
H32A 0.3596 -0.0172 0.5851 0.04 Uiso calc 1 . . H
H32B 0.2989 -0.0179 0.6559 0.04 Uiso calc 1 . . H
H32C 0.3767 -0.1523 0.6672 0.04 Uiso calc 1 . . H
C33 0.8240(4) 0.3787(13) 0.7612(5) 0.0241(17) Uani d 1 . . C
C34 0.8632(5) 0.2081(13) 0.7974(5) 0.0260(18) Uani d 1 . . C
C35 0.9415(5) 0.2099(15) 0.8120(6) 0.037(2) Uani d 1 . . C
H35 0.9663 0.0868 0.8352 0.045 Uiso calc 1 . . H
C36 0.9843(5) 0.3903(15) 0.7929(6) 0.038(2) Uani d 1 . . C
H36 1.0379 0.3973 0.8052 0.045 Uiso calc 1 . . H
C37 0.9458(5) 0.5568(15) 0.7557(6) 0.035(2) Uani d 1 . . C
C38 0.8673(5) 0.5571(14) 0.7395(5) 0.0289(18) Uani d 1 . . C
H38 0.8432 0.678 0.7138 0.035 Uiso calc 1 . . H
C39 0.7497(4) 0.2632(12) 0.6047(5) 0.0237(17) Uani d 1 . . C
C40 0.8114(4) 0.1429(13) 0.5778(5) 0.0272(18) Uani d 1 . . C
C41 0.8499(5) 0.1794(14) 0.5068(5) 0.0309(19) Uani d 1 . . C
H41 0.8929 0.0946 0.4933 0.037 Uiso calc 1 . . H
C42 0.8235(5) 0.3441(14) 0.4563(6) 0.032(2) Uani d 1 . . C
H42 0.848 0.3716 0.4065 0.039 Uiso calc 1 . . H
C43 0.7611(5) 0.4712(13) 0.4776(5) 0.0259(18) Uani d 1 . . C
H43 0.7439 0.5875 0.4438 0.031 Uiso calc 1 . . H
C44 0.7252(5) 0.4228(13) 0.5491(5) 0.0282(18) Uani d 1 . . C
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C12 . 1.403(8) ?
F2 C15 . 1.362(10) ?
F3 C22 . 1.350(9) ?
F4 C18 . 1.331(9) ?
O1 C5 . 1.381(10) ?
O1 C10 . 1.399(10) ?
N1 C1 . 1.479(10) ?
N1 C2 . 1.472(10) ?
N1 C11 . 1.421(10) ?
C1 H1 . 1 ?
C1 C8 . 1.520(10) ?
C1 C17 . 1.515(12) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.524(11) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.507(11) ?
C4 H4 . 0.95 ?
C4 C5 . 1.403(11) ?
C4 C9 . 1.401(11) ?
C5 C6 . 1.399(11) ?
C6 H6 . 0.95 ?
C6 C7 . 1.405(11) ?
C7 H7 . 0.95 ?
C7 C8 . 1.427(11) ?
C8 C9 . 1.386(11) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.390(11) ?
C11 C16 . 1.376(12) ?
C12 C13 . 1.364(12) ?
C13 H13 . 0.95 ?
C13 C14 . 1.373(13) ?
C14 H14 . 0.95 ?
C14 C15 . 1.355(13) ?
C15 C16 . 1.393(11) ?
C16 H16 . 0.95 ?
C17 C18 . 1.400(11) ?
C17 C22 . 1.403(12) ?
C18 C19 . 1.368(12) ?
C19 H19 . 0.95 ?
C19 C20 . 1.384(12) ?
C20 H20 . 0.95 ?
C20 C21 . 1.420(12) ?
C21 H21 . 0.95 ?
C21 C22 . 1.363(12) ?
F5 C34 . 1.371(9) ?
F6 C37 . 1.376(11) ?
F7 C40 . 1.348(9) ?
F8 C44 . 1.325(10) ?
O2 C27 . 1.373(9) ?
O2 C32 . 1.436(9) ?
N2 C23 . 1.474(10) ?
N2 C24 . 1.461(10) ?
N2 C33 . 1.425(10) ?
C23 H23 . 1 ?
C23 C30 . 1.520(11) ?
C23 C39 . 1.521(12) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C24 C25 . 1.565(13) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C25 C31 . 1.503(11) ?
C26 H26 . 0.95 ?
C26 C27 . 1.368(11) ?
C26 C31 . 1.393(12) ?
C27 C28 . 1.409(11) ?
C28 H28 . 0.95 ?
C28 C29 . 1.400(11) ?
C29 H29 . 0.95 ?
C29 C30 . 1.406(11) ?
C30 C31 . 1.379(12) ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C33 C34 . 1.381(11) ?
C33 C38 . 1.394(12) ?
C34 C35 . 1.379(12) ?
C35 H35 . 0.95 ?
C35 C36 . 1.388(14) ?
C36 H36 . 0.95 ?
C36 C37 . 1.363(13) ?
C37 C38 . 1.387(12) ?
C38 H38 . 0.95 ?
C39 C40 . 1.396(11) ?
C39 C44 . 1.400(11) ?
C40 C41 . 1.382(13) ?
C41 H41 . 0.95 ?
C41 C42 . 1.382(12) ?
C42 H42 . 0.95 ?
C42 C43 . 1.400(12) ?
C43 H43 . 0.95 ?
C43 C44 . 1.380(13) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 117.3(6) . . ?
C2 N1 C1 114.5(7) . . ?
C11 N1 C1 114.1(6) . . ?
C11 N1 C2 114.9(6) . . ?
N1 C1 H1 106.1 . . ?
N1 C1 C8 110.5(6) . . ?
N1 C1 C17 114.2(6) . . ?
C8 C1 H1 106.1 . . ?
C17 C1 H1 106.1 . . ?
C17 C1 C8 113.1(6) . . ?
N1 C2 H2A 110.3 . . ?
N1 C2 H2B 110.3 . . ?
N1 C2 C3 106.9(7) . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C9 C3 C2 113.4(7) . . ?
C9 C3 H3A 108.9 . . ?
C9 C3 H3B 108.9 . . ?
C5 C4 H4 120 . . ?
C9 C4 H4 120 . . ?
C9 C4 C5 119.9(7) . . ?
O1 C5 C4 114.9(7) . . ?
O1 C5 C6 124.1(7) . . ?
C6 C5 C4 120.9(7) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(7) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.7(7) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C1 117.5(7) . . ?
C9 C8 C1 122.2(7) . . ?
C9 C8 C7 120.3(7) . . ?
C4 C9 C3 119.6(7) . . ?
C8 C9 C3 120.3(7) . . ?
C8 C9 C4 120.0(7) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 120.9(7) . . ?
C16 C11 N1 123.1(7) . . ?
C16 C11 C12 115.9(7) . . ?
C11 C12 F1 117.9(7) . . ?
C13 C12 F1 118.3(7) . . ?
C13 C12 C11 123.8(8) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(8) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.3(8) . . ?
C15 C14 H14 121.3 . . ?
F2 C15 C16 117.3(8) . . ?
C14 C15 F2 119.3(7) . . ?
C14 C15 C16 123.4(8) . . ?
C11 C16 C15 119.7(8) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C1 120.7(7) . . ?
C18 C17 C22 112.8(7) . . ?
C22 C17 C1 126.4(7) . . ?
F4 C18 C17 117.6(7) . . ?
F4 C18 C19 117.0(7) . . ?
C19 C18 C17 125.4(7) . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.2(7) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.7(8) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 121.5 . . ?
C22 C21 C20 116.9(8) . . ?
C22 C21 H21 121.5 . . ?
F3 C22 C17 116.2(7) . . ?
F3 C22 C21 117.9(7) . . ?
C21 C22 C17 125.9(8) . . ?
C27 O2 C32 115.6(6) . . ?
C24 N2 C23 115.2(6) . . ?
C33 N2 C23 113.8(6) . . ?
C33 N2 C24 113.6(7) . . ?
N2 C23 H23 106.1 . . ?
N2 C23 C30 110.9(6) . . ?
N2 C23 C39 112.7(6) . . ?
C30 C23 H23 106.1 . . ?
C30 C23 C39 114.2(7) . . ?
C39 C23 H23 106.1 . . ?
N2 C24 H24A 110.7 . . ?
N2 C24 H24B 110.7 . . ?
N2 C24 C25 105.3(7) . . ?
H24A C24 H24B 108.8 . . ?
C25 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C24 C25 H25A 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C31 C25 C24 114.6(7) . . ?
C31 C25 H25A 108.6 . . ?
C31 C25 H25B 108.6 . . ?
C27 C26 H26 119.2 . . ?
C27 C26 C31 121.7(7) . . ?
C31 C26 H26 119.2 . . ?
O2 C27 C28 124.5(7) . . ?
C26 C27 O2 115.1(7) . . ?
C26 C27 C28 120.4(7) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 C27 117.8(7) . . ?
C29 C28 H28 121.1 . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.1(7) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C23 118.2(7) . . ?
C31 C30 C23 122.0(7) . . ?
C31 C30 C29 119.8(7) . . ?
C26 C31 C25 120.7(7) . . ?
C30 C31 C25 120.2(7) . . ?
C30 C31 C26 119.1(7) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N2 119.9(7) . . ?
C34 C33 C38 116.8(7) . . ?
C38 C33 N2 123.1(7) . . ?
F5 C34 C33 119.4(7) . . ?
F5 C34 C35 117.9(7) . . ?
C35 C34 C33 122.7(8) . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.5(8) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 121.6 . . ?
C37 C36 C35 116.7(8) . . ?
C37 C36 H36 121.6 . . ?
F6 C37 C38 116.9(8) . . ?
C36 C37 F6 119.4(8) . . ?
C36 C37 C38 123.6(9) . . ?
C33 C38 H38 120.2 . . ?
C37 C38 C33 119.5(8) . . ?
C37 C38 H38 120.2 . . ?
C40 C39 C23 121.7(7) . . ?
C40 C39 C44 113.2(8) . . ?
C44 C39 C23 125.1(7) . . ?
F7 C40 C39 117.2(7) . . ?
F7 C40 C41 116.9(7) . . ?
C41 C40 C39 125.8(7) . . ?
C40 C41 H41 121.3 . . ?
C42 C41 C40 117.4(8) . . ?
C42 C41 H41 121.3 . . ?
C41 C42 H42 119.5 . . ?
C41 C42 C43 120.9(8) . . ?
C43 C42 H42 119.5 . . ?
C42 C43 H43 120.9 . . ?
C44 C43 C42 118.1(7) . . ?
C44 C43 H43 120.9 . . ?
F8 C44 C39 117.5(8) . . ?
F8 C44 C43 118.0(7) . . ?
C43 C44 C39 124.4(8) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C12 C13 C14 -179.5(8) . . . . ?
F2 C15 C16 C11 -179.5(7) . . . . ?
F4 C18 C19 C20 -176.9(7) . . . . ?
O1 C5 C6 C7 179.8(7) . . . . ?
N1 C1 C8 C7 -163.0(7) . . . . ?
N1 C1 C8 C9 14.9(10) . . . . ?
N1 C1 C17 C18 98.9(9) . . . . ?
N1 C1 C17 C22 -78.6(10) . . . . ?
N1 C2 C3 C9 -49.1(9) . . . . ?
N1 C11 C12 F1 4.5(11) . . . . ?
N1 C11 C12 C13 -175.3(8) . . . . ?
N1 C11 C16 C15 174.4(8) . . . . ?
C1 N1 C2 C3 66.2(8) . . . . ?
C1 N1 C11 C12 -72.6(9) . . . . ?
C1 N1 C11 C16 110.0(9) . . . . ?
C1 C8 C9 C3 -2.1(11) . . . . ?
C1 C8 C9 C4 -178.7(7) . . . . ?
C1 C17 C18 F4 1.2(11) . . . . ?
C1 C17 C18 C19 -177.2(8) . . . . ?
C1 C17 C22 F3 -6.3(12) . . . . ?
C1 C17 C22 C21 174.5(8) . . . . ?
C2 N1 C1 C8 -48.3(9) . . . . ?
C2 N1 C1 C17 80.5(8) . . . . ?
C2 N1 C11 C12 152.3(7) . . . . ?
C2 N1 C11 C16 -25.1(11) . . . . ?
C2 C3 C9 C4 -163.5(7) . . . . ?
C2 C3 C9 C8 19.9(11) . . . . ?
C4 C5 C6 C7 0.7(11) . . . . ?
C5 C4 C9 C3 -174.2(8) . . . . ?
C5 C4 C9 C8 2.4(11) . . . . ?
C5 C6 C7 C8 0.9(11) . . . . ?
C6 C7 C8 C1 177.1(7) . . . . ?
C6 C7 C8 C9 -0.8(11) . . . . ?
C7 C8 C9 C3 175.8(7) . . . . ?
C7 C8 C9 C4 -0.8(11) . . . . ?
C8 C1 C17 C18 -133.6(8) . . . . ?
C8 C1 C17 C22 48.9(10) . . . . ?
C9 C4 C5 O1 178.5(7) . . . . ?
C9 C4 C5 C6 -2.4(12) . . . . ?
C10 O1 C5 C4 -176.3(7) . . . . ?
C10 O1 C5 C6 4.6(11) . . . . ?
C11 N1 C1 C8 176.4(6) . . . . ?
C11 N1 C1 C17 -54.7(9) . . . . ?
C11 N1 C2 C3 -159.0(7) . . . . ?
C11 C12 C13 C14 0.2(13) . . . . ?
C12 C11 C16 C15 -3.1(12) . . . . ?
C12 C13 C14 C15 -1.8(13) . . . . ?
C13 C14 C15 F2 -177.9(8) . . . . ?
C13 C14 C15 C16 1.0(14) . . . . ?
C14 C15 C16 C11 1.6(13) . . . . ?
C16 C11 C12 F1 -178.0(7) . . . . ?
C16 C11 C12 C13 2.3(12) . . . . ?
C17 C1 C8 C7 67.5(9) . . . . ?
C17 C1 C8 C9 -114.6(8) . . . . ?
C17 C18 C19 C20 1.4(13) . . . . ?
C18 C17 C22 F3 176.0(7) . . . . ?
C18 C17 C22 C21 -3.2(12) . . . . ?
C18 C19 C20 C21 -1.3(13) . . . . ?
C19 C20 C21 C22 -0.9(12) . . . . ?
C20 C21 C22 F3 -175.9(7) . . . . ?
C20 C21 C22 C17 3.4(13) . . . . ?
C22 C17 C18 F4 179.0(7) . . . . ?
C22 C17 C18 C19 0.7(12) . . . . ?
F5 C34 C35 C36 -179.1(8) . . . . ?
F6 C37 C38 C33 -178.7(7) . . . . ?
F7 C40 C41 C42 -178.9(7) . . . . ?
O2 C27 C28 C29 -178.6(7) . . . . ?
N2 C23 C30 C29 -165.1(7) . . . . ?
N2 C23 C30 C31 15.0(10) . . . . ?
N2 C23 C39 C40 99.0(8) . . . . ?
N2 C23 C39 C44 -80.6(9) . . . . ?
N2 C24 C25 C31 -47.2(9) . . . . ?
N2 C33 C34 F5 4.3(11) . . . . ?
N2 C33 C34 C35 -177.2(8) . . . . ?
N2 C33 C38 C37 176.2(8) . . . . ?
C23 N2 C24 C25 65.5(9) . . . . ?
C23 N2 C33 C34 -72.6(9) . . . . ?
C23 N2 C33 C38 110.6(8) . . . . ?
C23 C30 C31 C25 -1.0(12) . . . . ?
C23 C30 C31 C26 -178.2(7) . . . . ?
C23 C39 C40 F7 0.9(11) . . . . ?
C23 C39 C40 C41 -175.4(8) . . . . ?
C23 C39 C44 F8 -4.2(11) . . . . ?
C23 C39 C44 C43 174.7(7) . . . . ?
C24 N2 C23 C30 -50.1(9) . . . . ?
C24 N2 C23 C39 79.4(9) . . . . ?
C24 N2 C33 C34 152.9(8) . . . . ?
C24 N2 C33 C38 -23.9(11) . . . . ?
C24 C25 C31 C26 -164.9(8) . . . . ?
C24 C25 C31 C30 18.0(11) . . . . ?
C26 C27 C28 C29 1.4(12) . . . . ?
C27 C26 C31 C25 -177.4(8) . . . . ?
C27 C26 C31 C30 -0.3(13) . . . . ?
C27 C28 C29 C30 0.1(12) . . . . ?
C28 C29 C30 C23 178.3(7) . . . . ?
C28 C29 C30 C31 -1.8(12) . . . . ?
C29 C30 C31 C25 179.0(8) . . . . ?
C29 C30 C31 C26 1.8(12) . . . . ?
C30 C23 C39 C40 -133.2(7) . . . . ?
C30 C23 C39 C44 47.2(10) . . . . ?
C31 C26 C27 O2 178.6(7) . . . . ?
C31 C26 C27 C28 -1.4(13) . . . . ?
C32 O2 C27 C26 -175.5(7) . . . . ?
C32 O2 C27 C28 4.5(11) . . . . ?
C33 N2 C23 C30 176.2(6) . . . . ?
C33 N2 C23 C39 -54.3(9) . . . . ?
C33 N2 C24 C25 -160.7(6) . . . . ?
C33 C34 C35 C36 2.3(14) . . . . ?
C34 C33 C38 C37 -0.8(12) . . . . ?
C34 C35 C36 C37 -3.4(14) . . . . ?
C35 C36 C37 F6 -179.3(8) . . . . ?
C35 C36 C37 C38 2.6(14) . . . . ?
C36 C37 C38 C33 -0.5(14) . . . . ?
C38 C33 C34 F5 -178.7(7) . . . . ?
C38 C33 C34 C35 -0.1(12) . . . . ?
C39 C23 C30 C29 66.3(9) . . . . ?
C39 C23 C30 C31 -113.7(8) . . . . ?
C39 C40 C41 C42 -2.6(13) . . . . ?
C40 C39 C44 F8 176.2(7) . . . . ?
C40 C39 C44 C43 -4.9(11) . . . . ?
C40 C41 C42 C43 1.3(12) . . . . ?
C41 C42 C43 C44 -2.1(12) . . . . ?
C42 C43 C44 F8 -177.0(7) . . . . ?
C42 C43 C44 C39 4.1(12) . . . . ?
C44 C39 C40 F7 -179.5(7) . . . . ?
C44 C39 C40 C41 4.2(12) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-19
_database_code_depnum_ccdc_archive 'CCDC 1540720'
 
_audit_creation_date                    2020-03-09T09:12:18-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          18.194(6)
_cell_length_b                          6.147(2)
_cell_length_c                          16.182(5)
_cell_angle_alpha                       90
_cell_angle_beta                        104.903(11)
_cell_angle_gamma                       90
_cell_volume                            1749.0(10)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           3693
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.3
_exptl_crystal_size_mid                 0.3
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           1.471
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.119
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.779
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100  #293(2)
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71075
_diffrn_measurement_device_type
;
        Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   11916
_diffrn_reflns_av_R_equivalents         0.0662
_diffrn_reflns_theta_min                3.112
_diffrn_reflns_theta_max                27.524
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.984
_diffrn_measured_fraction_theta_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_full
                                        0.995
_diffrn_reflns_Laue_measured_fraction_max
                                        0.984
_diffrn_reflns_point_group_measured_fraction_full
                                        0.995
_diffrn_reflns_point_group_measured_fraction_max
                                        0.984
_diffrn_reflns_limit_h_min              -23
_diffrn_reflns_limit_h_max              23
_diffrn_reflns_limit_k_min              -6
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -20
_diffrn_reflns_limit_l_max              21
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3963
_reflns_number_gt                       2613
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0982
_refine_ls_R_factor_gt                  0.0658
_refine_ls_wR_factor_ref                0.1916
_refine_ls_goodness_of_fit_ref          1.072
_refine_ls_restrained_S_all             1.072
_refine_ls_number_reflns                3963
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0973P)²+0.0745P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.379
_refine_diff_density_min                -0.382
_refine_diff_density_rms                0.075
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.86240(8) 0.1093(2) 0.70468(10) 0.0348(4) Uani d 1 . . F
F2 0.80120(8) 0.7590(2) 0.54908(10) 0.0320(4) Uani d 1 . . F
F3 0.85387(8) 0.7235(3) 0.77573(9) 0.0323(4) Uani d 1 . . F
F4 0.93400(9) 0.5665(3) 0.92468(10) 0.0387(4) Uani d 1 . . F
O1 0.39732(10) 0.4549(3) 0.62654(11) 0.0300(4) Uani d 1 . . O
N1 0.74705(11) 0.4056(3) 0.61550(13) 0.0241(5) Uani d 1 . . N
C1 0.71641(13) 0.5372(4) 0.67590(15) 0.0232(5) Uani d 1 . . C
H1 0.7293 0.6898 0.6692 0.028 Uiso calc 1 . . H
C2 0.71701(14) 0.1834(4) 0.60521(17) 0.0266(6) Uani d 1 . . C
H2A 0.7246 0.1146 0.6607 0.032 Uiso calc 1 . . H
H2B 0.7436 0.0984 0.5714 0.032 Uiso calc 1 . . H
C3 0.63251(14) 0.1925(4) 0.56059(17) 0.0277(6) Uani d 1 . . C
H3A 0.626 0.2356 0.5015 0.033 Uiso calc 1 . . H
H3B 0.6105 0.0489 0.561 0.033 Uiso calc 1 . . H
C4 0.51260(14) 0.3291(4) 0.59238(15) 0.0254(5) Uani d 1 . . C
H4 0.4866 0.2171 0.5585 0.031 Uiso calc 1 . . H
C5 0.47342(14) 0.4717(4) 0.63086(15) 0.0268(6) Uani d 1 . . C
C6 0.51182(14) 0.6458(4) 0.67812(16) 0.0280(6) Uani d 1 . . C
H6 0.4852 0.7476 0.7016 0.034 Uiso calc 1 . . H
C7 0.58926(14) 0.6670(4) 0.69000(16) 0.0269(6) Uani d 1 . . C
H7 0.6146 0.782 0.7225 0.032 Uiso calc 1 . . H
C8 0.63044(14) 0.5184(4) 0.65400(15) 0.0238(5) Uani d 1 . . C
C9 0.59135(14) 0.3510(4) 0.60373(15) 0.0246(5) Uani d 1 . . C
C10 0.35839(15) 0.2657(5) 0.58406(18) 0.0333(6) Uani d 1 . . C
H10A 0.3561 0.2728 0.5242 0.05 Uiso calc 1 . . H
H10B 0.3077 0.2613 0.5914 0.05 Uiso calc 1 . . H
H10C 0.3854 0.137 0.6082 0.05 Uiso calc 1 . . H
C11 0.82646(14) 0.4300(4) 0.62472(15) 0.0232(5) Uani d 1 . . C
C12 0.85332(14) 0.6101(4) 0.58914(15) 0.0262(6) Uani d 1 . . C
C13 0.92856(15) 0.6460(5) 0.59233(16) 0.0294(6) Uani d 1 . . C
H13 0.9435 0.7703 0.5682 0.035 Uiso calc 1 . . H
C14 0.98156(15) 0.4923(5) 0.63241(16) 0.0308(6) Uani d 1 . . C
H14 1.0327 0.5122 0.6345 0.037 Uiso calc 1 . . H
C15 0.95900(14) 0.3097(4) 0.66929(16) 0.0301(6) Uani d 1 . . C
H15 0.9943 0.2057 0.696 0.036 Uiso calc 1 . . H
C16 0.88288(14) 0.2858(4) 0.66537(16) 0.0262(6) Uani d 1 . . C
C17 0.75366(14) 0.4698(4) 0.76840(15) 0.0246(5) Uani d 1 . . C
C18 0.82381(15) 0.5587(4) 0.81095(16) 0.0267(6) Uani d 1 . . C
C19 0.86490(14) 0.4797(5) 0.88938(16) 0.0296(6) Uani d 1 . . C
C20 0.83710(15) 0.3171(5) 0.92968(17) 0.0326(6) Uani d 1 . . C
H20 0.8652 0.2634 0.982 0.039 Uiso calc 1 . . H
C21 0.76588(15) 0.2335(5) 0.89078(17) 0.0320(6) Uani d 1 . . C
H21 0.7452 0.1258 0.9184 0.038 Uiso calc 1 . . H
C22 0.72489(14) 0.3077(4) 0.81143(16) 0.0274(6) Uani d 1 . . C
H22 0.6774 0.2482 0.7865 0.033 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C16 . 1.358(3) ?
F2 C12 . 1.357(3) ?
F3 C18 . 1.345(3) ?
F4 C19 . 1.350(3) ?
O1 C5 . 1.372(3) ?
O1 C10 . 1.441(3) ?
N1 C1 . 1.483(3) ?
N1 C2 . 1.465(3) ?
N1 C11 . 1.422(3) ?
C1 H1 . 0.98 ?
C1 C8 . 1.517(3) ?
C1 C17 . 1.533(3) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C2 C3 . 1.522(3) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C3 C9 . 1.505(3) ?
C4 H4 . 0.93 ?
C4 C5 . 1.376(4) ?
C4 C9 . 1.403(3) ?
C5 C6 . 1.394(4) ?
C6 H6 . 0.93 ?
C6 C7 . 1.378(4) ?
C7 H7 . 0.93 ?
C7 C8 . 1.400(3) ?
C8 C9 . 1.389(4) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 C12 . 1.393(4) ?
C11 C16 . 1.387(3) ?
C12 C13 . 1.374(4) ?
C13 H13 . 0.93 ?
C13 C14 . 1.386(4) ?
C14 H14 . 0.93 ?
C14 C15 . 1.382(4) ?
C15 H15 . 0.93 ?
C15 C16 . 1.378(4) ?
C17 C18 . 1.396(3) ?
C17 C22 . 1.393(4) ?
C18 C19 . 1.385(4) ?
C19 C20 . 1.360(4) ?
C20 H20 . 0.93 ?
C20 C21 . 1.386(4) ?
C21 H21 . 0.93 ?
C21 C22 . 1.386(4) ?
C22 H22 . 0.93 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.8(2) . . ?
C2 N1 C1 113.01(19) . . ?
C11 N1 C1 114.68(19) . . ?
C11 N1 C2 116.70(19) . . ?
N1 C1 H1 108 . . ?
N1 C1 C8 110.15(19) . . ?
N1 C1 C17 110.45(19) . . ?
C8 C1 H1 108 . . ?
C8 C1 C17 112.2(2) . . ?
C17 C1 H1 108 . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 C3 108.7(2) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108 . . ?
C9 C3 C2 111.5(2) . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C9 120.7(2) . . ?
C9 C4 H4 119.7 . . ?
O1 C5 C4 124.2(2) . . ?
O1 C5 C6 116.3(2) . . ?
C4 C5 C6 119.5(2) . . ?
C5 C6 H6 120 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C1 118.9(2) . . ?
C9 C8 C1 122.3(2) . . ?
C9 C8 C7 118.6(2) . . ?
C4 C9 C3 119.4(2) . . ?
C8 C9 C3 120.7(2) . . ?
C8 C9 C4 119.9(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 119.7(2) . . ?
C16 C11 N1 126.2(2) . . ?
C16 C11 C12 114.1(2) . . ?
F2 C12 C11 117.2(2) . . ?
F2 C12 C13 118.4(2) . . ?
C13 C12 C11 124.3(2) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.3(3) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.9 . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 H15 120.9 . . ?
F1 C16 C11 118.3(2) . . ?
F1 C16 C15 117.2(2) . . ?
C15 C16 C11 124.5(2) . . ?
C18 C17 C1 119.6(2) . . ?
C22 C17 C1 123.6(2) . . ?
C22 C17 C18 116.6(2) . . ?
F3 C18 C17 120.4(2) . . ?
F3 C18 C19 118.0(2) . . ?
C19 C18 C17 121.6(2) . . ?
F4 C19 C18 118.3(2) . . ?
F4 C19 C20 120.6(2) . . ?
C20 C19 C18 121.2(2) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.3(2) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(3) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.1(2) . . ?
C21 C22 H22 119.4 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F2 C12 C13 C14 -179.2(2) . . . . ?
F3 C18 C19 F4 -2.4(4) . . . . ?
F3 C18 C19 C20 178.3(2) . . . . ?
F4 C19 C20 C21 180.0(2) . . . . ?
O1 C5 C6 C7 176.1(2) . . . . ?
N1 C1 C8 C7 -165.5(2) . . . . ?
N1 C1 C8 C9 18.6(3) . . . . ?
N1 C1 C17 C18 84.0(3) . . . . ?
N1 C1 C17 C22 -90.0(3) . . . . ?
N1 C2 C3 C9 -50.7(3) . . . . ?
N1 C11 C12 F2 2.0(3) . . . . ?
N1 C11 C12 C13 -178.1(2) . . . . ?
N1 C11 C16 F1 -3.9(4) . . . . ?
N1 C11 C16 C15 176.6(2) . . . . ?
C1 N1 C2 C3 67.2(3) . . . . ?
C1 N1 C11 C12 -80.0(3) . . . . ?
C1 N1 C11 C16 101.6(3) . . . . ?
C1 C8 C9 C3 -6.6(4) . . . . ?
C1 C8 C9 C4 173.7(2) . . . . ?
C1 C17 C18 F3 8.9(4) . . . . ?
C1 C17 C18 C19 -170.2(2) . . . . ?
C1 C17 C22 C21 171.5(2) . . . . ?
C2 N1 C1 C8 -49.2(3) . . . . ?
C2 N1 C1 C17 75.3(3) . . . . ?
C2 N1 C11 C12 144.5(2) . . . . ?
C2 N1 C11 C16 -33.9(3) . . . . ?
C2 C3 C9 C4 -157.9(2) . . . . ?
C2 C3 C9 C8 22.4(3) . . . . ?
C4 C5 C6 C7 -3.7(4) . . . . ?
C5 C4 C9 C3 -179.9(2) . . . . ?
C5 C4 C9 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C6 C7 C8 C1 -174.4(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C7 C8 C9 C3 177.4(2) . . . . ?
C7 C8 C9 C4 -2.2(4) . . . . ?
C8 C1 C17 C18 -152.7(2) . . . . ?
C8 C1 C17 C22 33.4(3) . . . . ?
C9 C4 C5 O1 -176.5(2) . . . . ?
C9 C4 C5 C6 3.2(4) . . . . ?
C10 O1 C5 C4 4.8(3) . . . . ?
C10 O1 C5 C6 -174.9(2) . . . . ?
C11 N1 C1 C8 173.67(19) . . . . ?
C11 N1 C1 C17 -61.8(3) . . . . ?
C11 N1 C2 C3 -156.6(2) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C11 C16 F1 177.6(2) . . . . ?
C12 C11 C16 C15 -1.9(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 F1 -177.7(2) . . . . ?
C14 C15 C16 C11 1.9(4) . . . . ?
C16 C11 C12 F2 -179.4(2) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C17 C1 C8 C7 71.0(3) . . . . ?
C17 C1 C8 C9 -104.9(3) . . . . ?
C17 C18 C19 F4 176.7(2) . . . . ?
C17 C18 C19 C20 -2.5(4) . . . . ?
C18 C17 C22 C21 -2.7(4) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 2.2(4) . . . . ?
C20 C21 C22 C17 -0.4(4) . . . . ?
C22 C17 C18 F3 -176.7(2) . . . . ?
C22 C17 C18 C19 4.2(4) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-21
_database_code_depnum_ccdc_archive 'CCDC 1540722'
 
_audit_creation_date                    2020-03-09T09:13:28-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
_chemical_absolute_configuration        unk
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 n 1'
_symmetry_space_group_name_Hall         'P -2yac'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y, z+1/2'

_cell_length_a                          7.6714(11)
_cell_length_b                          7.1287(9)
_cell_length_c                          16.428(2)
_cell_angle_alpha                       90
_cell_angle_beta                        100.298(6)
_cell_angle_gamma                       90
_cell_volume                            883.9(2)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           2379
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.1
_exptl_crystal_density_diffrn           1.455
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    400
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.868
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   4823
_diffrn_reflns_av_R_equivalents         0.034
_diffrn_reflns_theta_min                3.123
_diffrn_reflns_theta_max                25.026
_diffrn_reflns_theta_full               25.026
_diffrn_measured_fraction_theta_max
                                        0.997
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.997
_diffrn_reflns_point_group_measured_fraction_full
                                        0.834
_diffrn_reflns_point_group_measured_fraction_max
                                        0.834
_diffrn_reflns_limit_h_min              -9
_diffrn_reflns_limit_h_max              9
_diffrn_reflns_limit_k_min              -8
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min              -19
_diffrn_reflns_limit_l_max              19
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    2621
_reflns_number_gt                       2379
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0444
_refine_ls_R_factor_gt                  0.0386
_refine_ls_wR_factor_ref                0.0949
_refine_ls_goodness_of_fit_ref          1.098
_refine_ls_restrained_S_all             1.098
_refine_ls_number_reflns                2621
_refine_ls_number_parameters            254
_refine_ls_number_restraints            2
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0476P)²+0.1042P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.19
_refine_diff_density_min                -0.18
_refine_diff_density_rms                0.044
_refine_ls_extinction_method            none
_refine_ls_abs_structure_details
;
 Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          -0.5(6)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F3 0.5886(3) 0.8393(3) 0.58570(13) 0.0293(5) Uani d 1 . . F
F1 0.2248(3) 0.7416(3) 0.38794(13) 0.0314(6) Uani d 1 . . F
F2 0.3071(3) 0.4291(3) 0.64399(14) 0.0363(6) Uani d 1 . . F
F4 0.8992(3) 0.2142(3) 0.73338(13) 0.0388(6) Uani d 1 . . F
O1 0.9452(4) 0.0709(4) 0.28952(16) 0.0311(7) Uani d 1 . . O
N1 0.3809(4) 0.4506(4) 0.47872(18) 0.0222(7) Uani d 1 . . N
C5 0.8430(5) 0.1682(5) 0.3351(2) 0.0229(8) Uani d 1 . . C
C11 0.2725(5) 0.5778(5) 0.5142(2) 0.0222(8) Uani d 1 . . C
C9 0.5941(5) 0.2123(5) 0.4051(2) 0.0205(8) Uani d 1 . . C
C8 0.6589(5) 0.3877(5) 0.43162(19) 0.0193(8) Uani d 1 . . C
C4 0.6877(5) 0.1034(5) 0.3563(2) 0.0244(8) Uani d 1 . . C
H4 0.6436 -0.0165 0.3376 0.029 Uiso calc 1 . . H
C17 0.6640(5) 0.5202(5) 0.5748(2) 0.0215(8) Uani d 1 . . C
C16 0.2345(5) 0.5713(5) 0.5935(2) 0.0263(9) Uani d 1 . . C
C19 0.7330(5) 0.6867(5) 0.7056(2) 0.0253(9) Uani d 1 . . C
H19 0.7277 0.7996 0.7358 0.03 Uiso calc 1 . . H
C21 0.8178(6) 0.3712(5) 0.6968(2) 0.0277(9) Uani d 1 . . C
C18 0.6624(5) 0.6792(5) 0.6225(2) 0.0235(8) Uani d 1 . . C
C1 0.5657(5) 0.5128(5) 0.4846(2) 0.0208(8) Uani d 1 . . C
H1 0.5636 0.6427 0.4615 0.025 Uiso calc 1 . . H
C22 0.7476(5) 0.3634(5) 0.6137(2) 0.0235(8) Uani d 1 . . C
H22 0.7563 0.2515 0.5833 0.028 Uiso calc 1 . . H
C13 0.0889(5) 0.8596(5) 0.4945(3) 0.0293(9) Uani d 1 . . C
H13 0.0388 0.9595 0.4597 0.035 Uiso calc 1 . . H
C12 0.1954(5) 0.7272(5) 0.4667(2) 0.0231(8) Uani d 1 . . C
C7 0.8167(5) 0.4512(5) 0.4100(2) 0.0240(8) Uani d 1 . . C
H7 0.8612 0.5711 0.4286 0.029 Uiso calc 1 . . H
C20 0.8116(5) 0.5286(5) 0.7446(2) 0.0274(9) Uani d 1 . . C
H20 0.8593 0.5285 0.8021 0.033 Uiso calc 1 . . H
C2 0.3651(5) 0.2503(5) 0.4962(2) 0.0226(8) Uani d 1 . . C
H2A 0.2408 0.2192 0.4995 0.027 Uiso calc 1 . . H
H2B 0.4405 0.2184 0.5498 0.027 Uiso calc 1 . . H
C6 0.9093(5) 0.3445(5) 0.3626(2) 0.0268(9) Uani d 1 . . C
H6 1.0167 0.3897 0.3487 0.032 Uiso calc 1 . . H
C3 0.4238(5) 0.1402(5) 0.4270(2) 0.0236(8) Uani d 1 . . C
H3A 0.4397 0.0071 0.4439 0.028 Uiso calc 1 . . H
H3B 0.3295 0.1459 0.3774 0.028 Uiso calc 1 . . H
C15 0.1296(5) 0.6977(5) 0.6249(3) 0.0318(9) Uani d 1 . . C
H15 0.1072 0.686 0.6797 0.038 Uiso calc 1 . . H
C10 0.8790(6) -0.1046(5) 0.2545(2) 0.0326(10) Uani d 1 . . C
H10A 0.7654 -0.0844 0.2174 0.049 Uiso calc 1 . . H
H10B 0.8621 -0.1908 0.2989 0.049 Uiso calc 1 . . H
H10C 0.9641 -0.1587 0.2232 0.049 Uiso calc 1 . . H
C14 0.0572(5) 0.8429(5) 0.5741(3) 0.0311(9) Uani d 1 . . C
H14 -0.0156 0.9329 0.5945 0.037 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F3 C18 . 1.366(4) ?
F1 C12 . 1.357(4) ?
F2 C16 . 1.364(4) ?
F4 C21 . 1.368(4) ?
O1 C5 . 1.365(4) ?
O1 C10 . 1.432(4) ?
N1 C11 . 1.424(5) ?
N1 C1 . 1.471(5) ?
N1 C2 . 1.465(4) ?
C5 C4 . 1.380(5) ?
C5 C6 . 1.400(5) ?
C11 C16 . 1.386(5) ?
C11 C12 . 1.388(5) ?
C9 C8 . 1.387(5) ?
C9 C4 . 1.403(5) ?
C9 C3 . 1.506(5) ?
C8 C1 . 1.512(5) ?
C8 C7 . 1.396(5) ?
C4 H4 . 0.95 ?
C17 C18 . 1.379(5) ?
C17 C1 . 1.538(5) ?
C17 C22 . 1.387(5) ?
C16 C15 . 1.369(5) ?
C19 H19 . 0.95 ?
C19 C18 . 1.378(5) ?
C19 C20 . 1.381(5) ?
C21 C22 . 1.376(5) ?
C21 C20 . 1.376(5) ?
C1 H1 . 1 ?
C22 H22 . 0.95 ?
C13 H13 . 0.95 ?
C13 C12 . 1.378(5) ?
C13 C14 . 1.378(6) ?
C7 H7 . 0.95 ?
C7 C6 . 1.374(5) ?
C20 H20 . 0.95 ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.514(5) ?
C6 H6 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C15 H15 . 0.95 ?
C15 C14 . 1.382(6) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C14 H14 . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 117.8(3) . . ?
C11 N1 C1 114.0(3) . . ?
C11 N1 C2 117.7(3) . . ?
C2 N1 C1 113.1(3) . . ?
O1 C5 C4 125.1(3) . . ?
O1 C5 C6 115.0(3) . . ?
C4 C5 C6 119.9(3) . . ?
C16 C11 N1 126.9(3) . . ?
C16 C11 C12 114.4(3) . . ?
C12 C11 N1 118.7(3) . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 C3 120.7(3) . . ?
C4 C9 C3 120.2(3) . . ?
C9 C8 C1 122.2(3) . . ?
C9 C8 C7 119.4(3) . . ?
C7 C8 C1 118.4(3) . . ?
C5 C4 C9 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C9 C4 H4 119.6 . . ?
C18 C17 C1 121.5(3) . . ?
C18 C17 C22 116.8(3) . . ?
C22 C17 C1 121.5(3) . . ?
F2 C16 C11 117.7(3) . . ?
F2 C16 C15 117.7(3) . . ?
C15 C16 C11 124.7(4) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
F4 C21 C22 118.0(3) . . ?
F4 C21 C20 118.4(3) . . ?
C20 C21 C22 123.6(4) . . ?
F3 C18 C17 118.7(3) . . ?
F3 C18 C19 117.7(3) . . ?
C19 C18 C17 123.6(3) . . ?
N1 C1 C8 109.5(3) . . ?
N1 C1 C17 112.0(3) . . ?
N1 C1 H1 107.7 . . ?
C8 C1 C17 111.9(3) . . ?
C8 C1 H1 107.7 . . ?
C17 C1 H1 107.7 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.4(3) . . ?
C21 C22 H22 120.3 . . ?
C12 C13 H13 121 . . ?
C12 C13 C14 118.1(4) . . ?
C14 C13 H13 121 . . ?
F1 C12 C11 117.8(3) . . ?
F1 C12 C13 118.2(3) . . ?
C13 C12 C11 123.9(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C19 C20 H20 121.4 . . ?
C21 C20 C19 117.2(3) . . ?
C21 C20 H20 121.4 . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
N1 C2 C3 108.2(3) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
C9 C3 C2 112.9(3) . . ?
C9 C3 H3A 109 . . ?
C9 C3 H3B 109 . . ?
C2 C3 H3A 109 . . ?
C2 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
C16 C15 H15 121.1 . . ?
C16 C15 C14 117.8(3) . . ?
C14 C15 H15 121.1 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F2 C16 C15 C14 179.4(3) . . . . ?
F4 C21 C22 C17 180.0(3) . . . . ?
F4 C21 C20 C19 178.2(3) . . . . ?
O1 C5 C4 C9 178.5(3) . . . . ?
O1 C5 C6 C7 -179.0(3) . . . . ?
N1 C11 C16 F2 -0.1(6) . . . . ?
N1 C11 C16 C15 179.8(4) . . . . ?
N1 C11 C12 F1 1.4(5) . . . . ?
N1 C11 C12 C13 -179.7(3) . . . . ?
N1 C2 C3 C9 46.1(4) . . . . ?
C11 N1 C1 C8 -169.4(3) . . . . ?
C11 N1 C1 C17 65.8(4) . . . . ?
C11 N1 C2 C3 155.6(3) . . . . ?
C11 C16 C15 C14 -0.5(6) . . . . ?
C9 C8 C1 N1 -18.4(4) . . . . ?
C9 C8 C1 C17 106.4(4) . . . . ?
C9 C8 C7 C6 0.4(5) . . . . ?
C8 C9 C4 C5 0.4(5) . . . . ?
C8 C9 C3 C2 -15.3(5) . . . . ?
C8 C7 C6 C5 0.2(6) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C4 C9 C8 C1 -179.8(3) . . . . ?
C4 C9 C8 C7 -0.7(5) . . . . ?
C4 C9 C3 C2 165.7(3) . . . . ?
C16 C11 C12 F1 -179.2(3) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C16 C15 C14 C13 0.3(6) . . . . ?
C18 C17 C1 N1 -88.8(4) . . . . ?
C18 C17 C1 C8 147.8(3) . . . . ?
C18 C17 C22 C21 2.3(5) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C1 N1 C11 C16 -95.1(4) . . . . ?
C1 N1 C11 C12 84.2(4) . . . . ?
C1 N1 C2 C3 -67.9(4) . . . . ?
C1 C8 C7 C6 179.5(3) . . . . ?
C1 C17 C18 F3 -7.4(5) . . . . ?
C1 C17 C18 C19 173.2(4) . . . . ?
C1 C17 C22 C21 -173.2(3) . . . . ?
C22 C17 C18 F3 177.1(3) . . . . ?
C22 C17 C18 C19 -2.3(5) . . . . ?
C22 C17 C1 N1 86.5(4) . . . . ?
C22 C17 C1 C8 -36.9(5) . . . . ?
C22 C21 C20 C19 -1.3(6) . . . . ?
C12 C11 C16 F2 -179.4(3) . . . . ?
C12 C11 C16 C15 0.4(6) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C7 C8 C1 N1 162.5(3) . . . . ?
C7 C8 C1 C17 -72.7(4) . . . . ?
C20 C19 C18 F3 -178.9(3) . . . . ?
C20 C19 C18 C17 0.5(6) . . . . ?
C20 C21 C22 C17 -0.6(6) . . . . ?
C2 N1 C11 C16 41.0(5) . . . . ?
C2 N1 C11 C12 -139.7(3) . . . . ?
C2 N1 C1 C8 52.5(4) . . . . ?
C2 N1 C1 C17 -72.3(4) . . . . ?
C6 C5 C4 C9 0.2(5) . . . . ?
C3 C9 C8 C1 1.2(5) . . . . ?
C3 C9 C8 C7 -179.7(3) . . . . ?
C3 C9 C4 C5 179.4(3) . . . . ?
C10 O1 C5 C4 6.0(5) . . . . ?
C10 O1 C5 C6 -175.7(3) . . . . ?
C14 C13 C12 F1 179.1(3) . . . . ?
C14 C13 C12 C11 0.1(6) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-23
_database_code_depnum_ccdc_archive 'CCDC 1540723'
 
_audit_creation_date                    2020-03-09T09:14:21-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P b c a'
_symmetry_space_group_name_Hall         '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                          16.643(3)
_cell_length_b                          6.1042(10)
_cell_length_c                          35.217(7)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            3577.8(11)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           5244
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.3
_exptl_crystal_size_mid                 0.1
_exptl_crystal_size_min                 0.1
_exptl_crystal_density_diffrn           1.438
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1600
_exptl_absorpt_coefficient_mu           0.117
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.809
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   22278
_diffrn_reflns_av_R_equivalents         0.1343
_diffrn_reflns_theta_min                3.369
_diffrn_reflns_theta_max                27.498
_diffrn_reflns_theta_full               26
_diffrn_measured_fraction_theta_max
                                        0.992
_diffrn_measured_fraction_theta_full
                                        0.993
_diffrn_reflns_Laue_measured_fraction_full
                                        0.993
_diffrn_reflns_Laue_measured_fraction_max
                                        0.992
_diffrn_reflns_point_group_measured_fraction_full
                                        0.993
_diffrn_reflns_point_group_measured_fraction_max
                                        0.992
_diffrn_reflns_limit_h_min              -19
_diffrn_reflns_limit_h_max              21
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -45
_diffrn_reflns_limit_l_max              45
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4056
_reflns_number_gt                       2658
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.1309
_refine_ls_R_factor_gt                  0.0901
_refine_ls_wR_factor_ref                0.2574
_refine_ls_goodness_of_fit_ref          1.144
_refine_ls_restrained_S_all             1.144
_refine_ls_number_reflns                4056
_refine_ls_number_parameters            258
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.354
_refine_diff_density_min                -0.304
_refine_diff_density_rms                0.075
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.70311(11) 0.9182(3) 0.41751(5) 0.0347(5) Uani d 1 . . F
F2 0.55386(13) 0.2761(3) 0.43739(6) 0.0483(6) Uani d 1 . . F
F3A 0.36031(19) 0.9050(6) 0.44782(9) 0.0462(8) Uani d 0.652(4) A 1 F
F3B 0.3126(4) 0.3663(10) 0.36523(16) 0.0462(8) Uani d 0.348(4) A 2 F
F4 0.26288(13) 0.6155(4) 0.41718(7) 0.0585(7) Uani d 1 . . F
O1 0.62593(16) 0.6603(4) 0.20393(7) 0.0432(7) Uani d 1 . . O
N1 0.63223(16) 0.5661(4) 0.38496(7) 0.0300(6) Uani d 1 . . N
C1 0.5801(2) 0.7183(5) 0.36328(9) 0.0298(7) Uani d 1 . . C
H1A 0.5974 0.8703 0.37 0.036 Uiso calc 0.652(4) A 1 H
H1B 0.5974 0.8703 0.37 0.036 Uiso calc 0.348(4) A 2 H
C2 0.6347(2) 0.3442(5) 0.36978(10) 0.0352(8) Uani d 1 . . C
H2A 0.5795 0.2864 0.3668 0.042 Uiso calc 1 . . H
H2B 0.6645 0.2469 0.3873 0.042 Uiso calc 1 . . H
C3 0.6764(2) 0.3514(5) 0.33171(9) 0.0354(8) Uani d 1 . . C
H3A 0.734 0.3855 0.3355 0.042 Uiso calc 1 . . H
H3B 0.6726 0.2059 0.3194 0.042 Uiso calc 1 . . H
C4 0.6517(2) 0.5086(5) 0.26689(9) 0.0342(8) Uani d 1 . . C
H4 0.6833 0.3932 0.2567 0.041 Uiso calc 1 . . H
C5 0.6183(2) 0.6619(5) 0.24299(9) 0.0331(8) Uani d 1 . . C
C6 0.5719(2) 0.8313(5) 0.25754(9) 0.0350(8) Uani d 1 . . C
H6 0.5485 0.9363 0.241 0.042 Uiso calc 1 . . H
C7 0.5602(2) 0.8460(5) 0.29616(9) 0.0334(8) Uani d 1 . . C
H7 0.529 0.9626 0.3062 0.04 Uiso calc 1 . . H
C8 0.59383(19) 0.6907(5) 0.32079(9) 0.0309(7) Uani d 1 . . C
C9 0.63924(19) 0.5220(5) 0.30614(9) 0.0323(7) Uani d 1 . . C
C10 0.6685(3) 0.4798(6) 0.18781(11) 0.0490(10) Uani d 1 . . C
H10A 0.6665 0.4896 0.1601 0.074 Uiso calc 1 . . H
H10B 0.6436 0.3423 0.196 0.074 Uiso calc 1 . . H
H10C 0.7246 0.4836 0.1963 0.074 Uiso calc 1 . . H
C11 0.63015(19) 0.5928(5) 0.42456(9) 0.0297(7) Uani d 1 . . C
C12 0.5954(2) 0.4517(6) 0.45075(10) 0.0360(8) Uani d 1 . . C
C13 0.6003(2) 0.4768(6) 0.48952(10) 0.0394(8) Uani d 1 . . C
H13 0.5772 0.3708 0.506 0.047 Uiso calc 1 . . H
C14 0.6390(2) 0.6568(6) 0.50415(10) 0.0405(9) Uani d 1 . . C
H14 0.6423 0.6772 0.5308 0.049 Uiso calc 1 . . H
C15 0.6734(2) 0.8092(6) 0.47961(10) 0.0357(8) Uani d 1 . . C
H15 0.6996 0.9359 0.4892 0.043 Uiso calc 1 . . H
C16 0.66849(19) 0.7718(5) 0.44123(9) 0.0317(7) Uani d 1 . . C
C17A 0.49246(19) 0.6963(5) 0.37528(9) 0.0294(7) Uani d 0.652(4) A 1 C
C17B 0.49246(19) 0.6963(5) 0.37528(9) 0.0294(7) Uani d 0.348(4) A 2 C
C18A 0.4646(2) 0.8260(6) 0.40485(9) 0.0346(8) Uani d 0.652(4) A 1 C
H18A 0.4984 0.935 0.4156 0.041 Uiso calc 0.652(4) A 1 H
C18B 0.4646(2) 0.8260(6) 0.40485(9) 0.0346(8) Uani d 0.348(4) A 2 C
H18B 0.4984 0.935 0.4156 0.041 Uiso calc 0.348(4) A 2 H
C19A 0.3877(2) 0.7964(6) 0.41862(10) 0.0397(8) Uani d 0.652(4) A 1 C
C19B 0.3877(2) 0.7964(6) 0.41862(10) 0.0397(8) Uani d 0.348(4) A 2 C
H19B 0.3688 0.8847 0.439 0.048 Uiso calc 0.348(4) A 2 H
C20A 0.3390(2) 0.6431(7) 0.40335(11) 0.0431(9) Uani d 0.652(4) A 1 C
C20B 0.3390(2) 0.6431(7) 0.40335(11) 0.0431(9) Uani d 0.348(4) A 2 C
C21A 0.3651(2) 0.5132(6) 0.37391(11) 0.0409(9) Uani d 0.652(4) A 1 C
H21A 0.3306 0.4052 0.3634 0.049 Uiso calc 0.652(4) A 1 H
C21B 0.3651(2) 0.5132(6) 0.37391(11) 0.0409(9) Uani d 0.348(4) A 2 C
C22A 0.4418(2) 0.5407(5) 0.35972(10) 0.0337(8) Uani d 0.652(4) A 1 C
H22A 0.4599 0.4524 0.3392 0.04 Uiso calc 0.652(4) A 1 H
C22B 0.4418(2) 0.5407(5) 0.35972(10) 0.0337(8) Uani d 0.348(4) A 2 C
H22B 0.4599 0.4524 0.3392 0.04 Uiso calc 0.348(4) A 2 H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C16 . 1.352(4) ?
F2 C12 . 1.360(4) ?
F3A C19A . 1.305(5) ?
F3B C21B . 1.289(7) ?
F4 C20A . 1.368(4) ?
F4 C20B . 1.368(4) ?
O1 C5 . 1.381(4) ?
O1 C10 . 1.427(4) ?
N1 C1 . 1.483(4) ?
N1 C2 . 1.457(4) ?
N1 C11 . 1.405(4) ?
C1 H1A . 1 ?
C1 H1B . 1 ?
C1 C8 . 1.523(4) ?
C1 C17A . 1.525(4) ?
C1 C17B . 1.525(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.510(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.509(5) ?
C4 H4 . 0.95 ?
C4 C5 . 1.376(5) ?
C4 C9 . 1.400(4) ?
C5 C6 . 1.388(4) ?
C6 H6 . 0.95 ?
C6 C7 . 1.377(4) ?
C7 H7 . 0.95 ?
C7 C8 . 1.401(4) ?
C8 C9 . 1.378(4) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.388(4) ?
C11 C16 . 1.395(5) ?
C12 C13 . 1.376(5) ?
C13 H13 . 0.95 ?
C13 C14 . 1.374(5) ?
C14 H14 . 0.95 ?
C14 C15 . 1.393(5) ?
C15 H15 . 0.95 ?
C15 C16 . 1.373(4) ?
C17A C18A . 1.388(5) ?
C17A C22A . 1.383(4) ?
C17B C18B . 1.388(5) ?
C17B C22B . 1.383(4) ?
C18A H18A . 0.95 ?
C18A C19A . 1.381(5) ?
C18B H18B . 0.95 ?
C18B C19B . 1.381(5) ?
C19A C20A . 1.350(5) ?
C19B H19B . 0.95 ?
C19B C20B . 1.350(5) ?
C20A C21A . 1.376(6) ?
C20B C21B . 1.376(6) ?
C21A H21A . 0.95 ?
C21A C22A . 1.381(5) ?
C21B C22B . 1.381(5) ?
C22A H22A . 0.95 ?
C22B H22B . 0.95 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.6(3) . . ?
C2 N1 C1 114.2(2) . . ?
C11 N1 C1 115.1(2) . . ?
C11 N1 C2 118.2(3) . . ?
N1 C1 H1A 106.9 . . ?
N1 C1 H1B 106.9 . . ?
N1 C1 C8 110.4(3) . . ?
N1 C1 C17A 111.2(2) . . ?
N1 C1 C17B 111.2(2) . . ?
C8 C1 H1A 106.9 . . ?
C8 C1 H1B 106.9 . . ?
C8 C1 C17A 114.0(3) . . ?
C8 C1 C17B 114.0(3) . . ?
C17A C1 H1A 106.9 . . ?
C17B C1 H1B 106.9 . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
N1 C2 C3 108.2(3) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
C9 C3 C2 111.2(3) . . ?
C9 C3 H3A 109.4 . . ?
C9 C3 H3B 109.4 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C9 120.3(3) . . ?
C9 C4 H4 119.9 . . ?
O1 C5 C6 115.1(3) . . ?
C4 C5 O1 124.5(3) . . ?
C4 C5 C6 120.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C1 118.3(3) . . ?
C9 C8 C1 122.2(3) . . ?
C9 C8 C7 119.5(3) . . ?
C4 C9 C3 119.2(3) . . ?
C8 C9 C3 121.1(3) . . ?
C8 C9 C4 119.6(3) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 126.7(3) . . ?
C12 C11 C16 113.4(3) . . ?
C16 C11 N1 119.8(3) . . ?
F2 C12 C11 118.1(3) . . ?
F2 C12 C13 117.5(3) . . ?
C13 C12 C11 124.4(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
F1 C16 C11 116.9(3) . . ?
F1 C16 C15 118.2(3) . . ?
C15 C16 C11 124.9(3) . . ?
C18A C17A C1 118.6(3) . . ?
C22A C17A C1 122.2(3) . . ?
C22A C17A C18A 119.0(3) . . ?
C18B C17B C1 118.6(3) . . ?
C22B C17B C1 122.2(3) . . ?
C22B C17B C18B 119.0(3) . . ?
C17A C18A H18A 120 . . ?
C19A C18A C17A 119.9(3) . . ?
C19A C18A H18A 120 . . ?
C17B C18B H18B 120 . . ?
C19B C18B C17B 119.9(3) . . ?
C19B C18B H18B 120 . . ?
F3A C19A C18A 122.2(4) . . ?
F3A C19A C20A 117.2(3) . . ?
C20A C19A C18A 120.5(3) . . ?
C18B C19B H19B 119.8 . . ?
C20B C19B C18B 120.5(3) . . ?
C20B C19B H19B 119.8 . . ?
F4 C20A C21A 119.4(3) . . ?
C19A C20A F4 120.0(4) . . ?
C19A C20A C21A 120.7(3) . . ?
F4 C20B C21B 119.4(3) . . ?
C19B C20B F4 120.0(4) . . ?
C19B C20B C21B 120.7(3) . . ?
C20A C21A H21A 120.2 . . ?
C20A C21A C22A 119.7(3) . . ?
C22A C21A H21A 120.2 . . ?
F3B C21B C20B 111.4(4) . . ?
F3B C21B C22B 128.7(4) . . ?
C20B C21B C22B 119.7(3) . . ?
C17A C22A H22A 119.9 . . ?
C21A C22A C17A 120.2(3) . . ?
C21A C22A H22A 119.9 . . ?
C17B C22B H22B 119.9 . . ?
C21B C22B C17B 120.2(3) . . ?
C21B C22B H22B 119.9 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F2 C12 C13 C14 -177.4(3) . . . . ?
F3A C19A C20A F4 3.6(5) . . . . ?
F3A C19A C20A C21A -176.3(4) . . . . ?
F3B C21B C22B C17B -173.7(5) . . . . ?
F4 C20A C21A C22A 179.8(3) . . . . ?
F4 C20B C21B F3B -4.9(5) . . . . ?
F4 C20B C21B C22B 179.8(3) . . . . ?
O1 C5 C6 C7 179.5(3) . . . . ?
N1 C1 C8 C7 -169.2(3) . . . . ?
N1 C1 C8 C9 9.4(4) . . . . ?
N1 C1 C17A C18A 89.6(3) . . . . ?
N1 C1 C17A C22A -85.4(4) . . . . ?
N1 C1 C17B C18B 89.6(3) . . . . ?
N1 C1 C17B C22B -85.4(4) . . . . ?
N1 C2 C3 C9 -51.9(4) . . . . ?
N1 C11 C12 F2 -5.0(5) . . . . ?
N1 C11 C12 C13 174.8(3) . . . . ?
N1 C11 C16 F1 3.1(4) . . . . ?
N1 C11 C16 C15 -177.0(3) . . . . ?
C1 N1 C2 C3 67.3(3) . . . . ?
C1 N1 C11 C12 108.8(4) . . . . ?
C1 N1 C11 C16 -73.9(4) . . . . ?
C1 C8 C9 C3 1.5(5) . . . . ?
C1 C8 C9 C4 -178.2(3) . . . . ?
C1 C17A C18A C19A -174.3(3) . . . . ?
C1 C17A C22A C21A 174.0(3) . . . . ?
C1 C17B C18B C19B -174.3(3) . . . . ?
C1 C17B C22B C21B 174.0(3) . . . . ?
C2 N1 C1 C8 -44.4(4) . . . . ?
C2 N1 C1 C17A 83.2(3) . . . . ?
C2 N1 C1 C17B 83.2(3) . . . . ?
C2 N1 C11 C12 -31.2(5) . . . . ?
C2 N1 C11 C16 146.1(3) . . . . ?
C2 C3 C9 C4 -160.3(3) . . . . ?
C2 C3 C9 C8 20.0(4) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C5 C4 C9 C3 179.9(3) . . . . ?
C5 C4 C9 C8 -0.5(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C1 178.8(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C3 -179.9(3) . . . . ?
C7 C8 C9 C4 0.4(5) . . . . ?
C8 C1 C17A C18A -144.8(3) . . . . ?
C8 C1 C17A C22A 40.2(4) . . . . ?
C8 C1 C17B C18B -144.8(3) . . . . ?
C8 C1 C17B C22B 40.2(4) . . . . ?
C9 C4 C5 O1 -178.8(3) . . . . ?
C9 C4 C5 C6 0.0(5) . . . . ?
C10 O1 C5 C4 3.1(5) . . . . ?
C10 O1 C5 C6 -175.8(3) . . . . ?
C11 N1 C1 C8 174.0(3) . . . . ?
C11 N1 C1 C17A -58.4(3) . . . . ?
C11 N1 C1 C17B -58.4(3) . . . . ?
C11 N1 C2 C3 -152.4(3) . . . . ?
C11 C12 C13 C14 2.8(6) . . . . ?
C12 C11 C16 F1 -179.3(3) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 F1 -178.9(3) . . . . ?
C14 C15 C16 C11 1.1(5) . . . . ?
C16 C11 C12 F2 177.6(3) . . . . ?
C16 C11 C12 C13 -2.7(5) . . . . ?
C17A C1 C8 C7 64.8(4) . . . . ?
C17A C1 C8 C9 -116.6(3) . . . . ?
C17A C18A C19A F3A 175.8(3) . . . . ?
C17A C18A C19A C20A -0.5(5) . . . . ?
C17B C1 C8 C7 64.8(4) . . . . ?
C17B C1 C8 C9 -116.6(3) . . . . ?
C17B C18B C19B C20B -0.5(5) . . . . ?
C18A C17A C22A C21A -1.0(5) . . . . ?
C18A C19A C20A F4 -179.9(3) . . . . ?
C18A C19A C20A C21A 0.2(6) . . . . ?
C18B C17B C22B C21B -1.0(5) . . . . ?
C18B C19B C20B F4 -179.9(3) . . . . ?
C18B C19B C20B C21B 0.2(6) . . . . ?
C19A C20A C21A C22A -0.3(6) . . . . ?
C19B C20B C21B F3B 175.0(4) . . . . ?
C19B C20B C21B C22B -0.3(6) . . . . ?
C20A C21A C22A C17A 0.7(5) . . . . ?
C20B C21B C22B C17B 0.7(5) . . . . ?
C22A C17A C18A C19A 0.9(5) . . . . ?
C22B C17B C18B C19B 0.9(5) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-25
_database_code_depnum_ccdc_archive 'CCDC 1540724'
 
_audit_creation_date                    2020-03-09T09:15:12-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          12.287(2)
_cell_length_b                          11.3169(16)
_cell_length_c                          22.191(4)
_cell_angle_alpha                       90
_cell_angle_beta                        145.954(6)
_cell_angle_gamma                       90
_cell_volume                            1727.5(5)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4671
_cell_measurement_theta_min             3.3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              plate
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.05
_exptl_crystal_density_diffrn           1.489
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.121
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.897
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   9203
_diffrn_reflns_av_R_equivalents         0.0293
_diffrn_reflns_theta_min                3.279
_diffrn_reflns_theta_max                25.02
_diffrn_reflns_theta_full               25.02
_diffrn_measured_fraction_theta_max
                                        0.996
_diffrn_measured_fraction_theta_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_max
                                        0.996
_diffrn_reflns_point_group_measured_fraction_full
                                        0.996
_diffrn_reflns_point_group_measured_fraction_max
                                        0.996
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min              -13
_diffrn_reflns_limit_k_max              13
_diffrn_reflns_limit_l_min              -26
_diffrn_reflns_limit_l_max              26
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3048
_reflns_number_gt                       2653
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0469
_refine_ls_R_factor_gt                  0.0402
_refine_ls_wR_factor_ref                0.106
_refine_ls_goodness_of_fit_ref          1.048
_refine_ls_restrained_S_all             1.048
_refine_ls_number_reflns                3048
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0543P)²+0.7613P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.25
_refine_diff_density_min                -0.255
_refine_diff_density_rms                0.05
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C8 0.2249(2) 0.72391(14) 0.61872(12) 0.0195(3) Uani d 1 . . C
C4 0.3663(2) 0.73774(14) 0.58421(13) 0.0212(3) Uani d 1 . . C
H4 0.4502 0.7069 0.5925 0.025 Uiso calc 1 . . H
C15 0.0370(2) 0.44127(15) 0.73539(13) 0.0243(4) Uani d 1 . . C
H15 -0.0155 0.4753 0.7469 0.029 Uiso calc 1 . . H
C17 0.3643(2) 0.71764(14) 0.78773(12) 0.0192(3) Uani d 1 . . C
C1 0.2156(2) 0.66377(13) 0.67552(12) 0.0194(3) Uani d 1 . . C
H1 0.0832 0.6787 0.6318 0.023 Uiso calc 1 . . H
C19 0.4608(2) 0.87807(14) 0.89717(14) 0.0236(4) Uani d 1 . . C
C12 0.1838(2) 0.34100(14) 0.69749(12) 0.0209(3) Uani d 1 . . C
H12 0.2294 0.305 0.6824 0.025 Uiso calc 1 . . H
C7 0.1095(2) 0.82226(14) 0.55285(12) 0.0218(4) Uani d 1 . . C
H7 0.0184 0.8497 0.54 0.026 Uiso calc 1 . . H
C13 0.1269(2) 0.27249(14) 0.71947(12) 0.0223(4) Uani d 1 . . C
C5 0.2569(2) 0.83850(14) 0.52277(12) 0.0215(4) Uani d 1 . . C
C9 0.3520(2) 0.68222(14) 0.63355(13) 0.0212(4) Uani d 1 . . C
C6 0.1269(2) 0.87998(14) 0.50627(13) 0.0229(4) Uani d 1 . . C
H6 0.0502 0.948 0.463 0.028 Uiso calc 1 . . H
C22 0.5340(2) 0.65984(15) 0.88284(13) 0.0246(4) Uani d 1 . . C
H22 0.5608 0.5836 0.8792 0.029 Uiso calc 1 . . H
C3 0.4684(3) 0.57472(15) 0.70266(14) 0.0257(4) Uani d 1 . . C
H3A 0.579 0.5977 0.7794 0.031 Uiso calc 1 . . H
H3B 0.5216 0.5392 0.6898 0.031 Uiso calc 1 . . H
C16 0.0993(2) 0.51245(15) 0.71704(13) 0.0224(4) Uani d 1 . . C
H16 0.0914 0.5959 0.7177 0.027 Uiso calc 1 . . H
C20 0.6300(3) 0.82142(16) 0.99097(14) 0.0272(4) Uani d 1 . . C
H20 0.7197 0.8571 1.0591 0.033 Uiso calc 1 . . H
C2 0.3436(3) 0.48446(15) 0.67797(15) 0.0263(4) Uani d 1 . . C
H2A 0.2485 0.4506 0.6057 0.032 Uiso calc 1 . . H
H2B 0.4274 0.4193 0.731 0.032 Uiso calc 1 . . H
C21 0.6650(2) 0.71069(16) 0.98284(14) 0.0278(4) Uani d 1 . . C
H21 0.7799 0.6691 1.0463 0.033 Uiso calc 1 . . H
C10 0.3929(3) 0.86034(17) 0.48680(14) 0.0292(4) Uani d 1 . . C
H10A 0.3796 0.91 0.4447 0.044 Uiso calc 1 . . H
H10B 0.3609 0.7784 0.4619 0.044 Uiso calc 1 . . H
H10C 0.527 0.8644 0.5631 0.044 Uiso calc 1 . . H
C18 0.3309(2) 0.82718(14) 0.79790(12) 0.0201(3) Uani d 1 . . C
C14 0.0521(2) 0.32080(15) 0.73672(12) 0.0239(4) Uani d 1 . . C
C11 0.1738(2) 0.46464(14) 0.69752(12) 0.0197(3) Uani d 1 . . C
N1 0.2394(2) 0.53582(12) 0.68117(11) 0.0219(3) Uani d 1 . . N
O1 0.26392(17) 0.90145(10) 0.47324(9) 0.0261(3) Uani d 1 . . O
F3 0.16558(13) 0.88711(8) 0.70918(7) 0.0252(2) Uani d 1 . . F
F2 -0.00326(14) 0.24851(9) 0.75736(8) 0.0311(3) Uani d 1 . . F
F4 0.41832(15) 0.98552(9) 0.90062(8) 0.0321(3) Uani d 1 . . F
F1 0.15068(14) 0.15437(8) 0.72718(8) 0.0303(3) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C8 C1 . 1.518(2) ?
C8 C7 . 1.397(2) ?
C8 C9 . 1.385(2) ?
C4 H4 . 0.95 ?
C4 C5 . 1.389(2) ?
C4 C9 . 1.394(2) ?
C15 H15 . 0.95 ?
C15 C16 . 1.384(2) ?
C15 C14 . 1.373(2) ?
C17 C1 . 1.540(2) ?
C17 C22 . 1.392(2) ?
C17 C18 . 1.382(2) ?
C1 H1 . 1 ?
C1 N1 . 1.462(2) ?
C19 C20 . 1.376(2) ?
C19 C18 . 1.380(2) ?
C19 F4 . 1.3506(19) ?
C12 H12 . 0.95 ?
C12 C13 . 1.376(2) ?
C12 C11 . 1.405(2) ?
C7 H7 . 0.95 ?
C7 C6 . 1.381(2) ?
C13 C14 . 1.368(2) ?
C13 F1 . 1.3487(19) ?
C5 C6 . 1.391(2) ?
C5 O1 . 1.3710(19) ?
C9 C3 . 1.498(2) ?
C6 H6 . 0.95 ?
C22 H22 . 0.95 ?
C22 C21 . 1.388(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C2 . 1.517(2) ?
C16 H16 . 0.95 ?
C16 C11 . 1.406(2) ?
C20 H20 . 0.95 ?
C20 C21 . 1.385(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 N1 . 1.461(2) ?
C21 H21 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.424(2) ?
C18 F3 . 1.3545(18) ?
C14 F2 . 1.3632(19) ?
C11 N1 . 1.384(2) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C7 C8 C1 121.16(14) . . ?
C9 C8 C1 119.72(14) . . ?
C9 C8 C7 119.11(15) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C9 119.46(15) . . ?
C9 C4 H4 120.3 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.10(16) . . ?
C22 C17 C1 123.06(14) . . ?
C18 C17 C1 120.28(14) . . ?
C18 C17 C22 116.64(15) . . ?
C8 C1 C17 111.13(13) . . ?
C8 C1 H1 107.4 . . ?
C17 C1 H1 107.4 . . ?
N1 C1 C8 111.60(13) . . ?
N1 C1 C17 111.62(13) . . ?
N1 C1 H1 107.4 . . ?
C20 C19 C18 121.33(16) . . ?
F4 C19 C20 120.26(15) . . ?
F4 C19 C18 118.42(15) . . ?
C13 C12 H12 120.3 . . ?
C13 C12 C11 119.41(15) . . ?
C11 C12 H12 120.3 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.56(15) . . ?
C6 C7 H7 119.7 . . ?
C14 C13 C12 122.03(15) . . ?
F1 C13 C12 118.87(15) . . ?
F1 C13 C14 119.08(15) . . ?
C4 C5 C6 120.09(15) . . ?
O1 C5 C4 124.14(15) . . ?
O1 C5 C6 115.75(14) . . ?
C8 C9 C4 120.74(15) . . ?
C8 C9 C3 116.90(14) . . ?
C4 C9 C3 122.35(15) . . ?
C7 C6 C5 119.95(15) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.68(16) . . ?
C21 C22 H22 119.2 . . ?
C9 C3 H3A 109.5 . . ?
C9 C3 H3B 109.5 . . ?
C9 C3 C2 110.79(14) . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C11 121.78(16) . . ?
C11 C16 H16 119.1 . . ?
C19 C20 H20 121.1 . . ?
C19 C20 C21 117.87(16) . . ?
C21 C20 H20 121.1 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C2 C3 112.27(14) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.62(16) . . ?
C20 C21 H21 119.7 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C19 C18 C17 121.84(15) . . ?
F3 C18 C17 120.16(14) . . ?
F3 C18 C19 117.99(14) . . ?
C13 C14 C15 120.06(15) . . ?
F2 C14 C15 120.46(15) . . ?
F2 C14 C13 119.46(15) . . ?
C12 C11 C16 117.56(15) . . ?
N1 C11 C12 120.66(14) . . ?
N1 C11 C16 121.76(15) . . ?
C2 N1 C1 120.74(13) . . ?
C11 N1 C1 118.72(13) . . ?
C11 N1 C2 120.37(13) . . ?
C5 O1 C10 117.31(13) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C8 C1 N1 C2 25.3(2) . . . . ?
C8 C1 N1 C11 -159.33(13) . . . . ?
C8 C7 C6 C5 1.5(2) . . . . ?
C8 C9 C3 C2 41.9(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C4 C5 O1 C10 -0.4(2) . . . . ?
C4 C9 C3 C2 -136.96(16) . . . . ?
C15 C16 C11 C12 -0.2(2) . . . . ?
C15 C16 C11 N1 -178.78(14) . . . . ?
C17 C1 N1 C2 -99.69(17) . . . . ?
C17 C1 N1 C11 75.65(18) . . . . ?
C17 C22 C21 C20 0.3(3) . . . . ?
C1 C8 C7 C6 176.51(14) . . . . ?
C1 C8 C9 C4 -178.50(14) . . . . ?
C1 C8 C9 C3 2.6(2) . . . . ?
C1 C17 C22 C21 -179.84(15) . . . . ?
C1 C17 C18 C19 179.92(15) . . . . ?
C1 C17 C18 F3 1.0(2) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
C12 C13 C14 F2 179.50(13) . . . . ?
C12 C11 N1 C1 176.42(14) . . . . ?
C12 C11 N1 C2 -8.2(2) . . . . ?
C7 C8 C1 C17 -90.43(18) . . . . ?
C7 C8 C1 N1 144.28(15) . . . . ?
C7 C8 C9 C4 0.4(2) . . . . ?
C7 C8 C9 C3 -178.48(14) . . . . ?
C13 C12 C11 C16 -2.0(2) . . . . ?
C13 C12 C11 N1 176.66(14) . . . . ?
C5 C4 C9 C8 2.4(2) . . . . ?
C5 C4 C9 C3 -178.78(15) . . . . ?
C9 C8 C1 C17 88.47(17) . . . . ?
C9 C8 C1 N1 -36.8(2) . . . . ?
C9 C8 C7 C6 -2.4(2) . . . . ?
C9 C4 C5 C6 -3.2(2) . . . . ?
C9 C4 C5 O1 178.25(14) . . . . ?
C9 C3 C2 N1 -51.37(19) . . . . ?
C6 C5 O1 C10 -178.93(14) . . . . ?
C22 C17 C1 C8 -106.69(17) . . . . ?
C22 C17 C1 N1 18.6(2) . . . . ?
C22 C17 C18 C19 1.3(2) . . . . ?
C22 C17 C18 F3 -177.66(14) . . . . ?
C3 C2 N1 C1 17.4(2) . . . . ?
C3 C2 N1 C11 -157.85(14) . . . . ?
C16 C15 C14 C13 -0.4(2) . . . . ?
C16 C15 C14 F2 178.28(14) . . . . ?
C16 C11 N1 C1 -5.0(2) . . . . ?
C16 C11 N1 C2 170.34(15) . . . . ?
C20 C19 C18 C17 -0.3(3) . . . . ?
C20 C19 C18 F3 178.65(14) . . . . ?
C18 C17 C1 C8 74.79(18) . . . . ?
C18 C17 C1 N1 -159.93(14) . . . . ?
C18 C17 C22 C21 -1.3(2) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C14 C15 C16 C11 1.3(2) . . . . ?
C11 C12 C13 C14 3.0(2) . . . . ?
C11 C12 C13 F1 -175.09(14) . . . . ?
O1 C5 C6 C7 179.94(14) . . . . ?
F4 C19 C20 C21 179.11(15) . . . . ?
F4 C19 C18 C17 179.84(14) . . . . ?
F4 C19 C18 F3 -1.2(2) . . . . ?
F1 C13 C14 C15 176.27(14) . . . . ?
F1 C13 C14 F2 -2.4(2) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-30
_database_code_depnum_ccdc_archive 'CCDC 1540726'
 
_audit_creation_date                    2020-03-09T09:16:15-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          12.947(3)
_cell_length_b                          10.4113(18)
_cell_length_c                          22.590(5)
_cell_angle_alpha                       90
_cell_angle_beta                        145.306(10)
_cell_angle_gamma                       90
_cell_volume                            1733.2(7)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           5100
_cell_measurement_theta_min             3.2
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.34
_exptl_crystal_size_mid                 0.3
_exptl_crystal_size_min                 0.25
_exptl_crystal_density_diffrn           1.484
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.12
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.912
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100 #373.3
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   18101
_diffrn_reflns_av_R_equivalents         0.0272
_diffrn_reflns_theta_min                3.169
_diffrn_reflns_theta_max                27.493
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max
                                        0.997
_diffrn_measured_fraction_theta_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_max
                                        0.997
_diffrn_reflns_point_group_measured_fraction_full
                                        0.996
_diffrn_reflns_point_group_measured_fraction_max
                                        0.997
_diffrn_reflns_limit_h_min              -16
_diffrn_reflns_limit_h_max              16
_diffrn_reflns_limit_k_min              -13
_diffrn_reflns_limit_k_max              13
_diffrn_reflns_limit_l_min              -29
_diffrn_reflns_limit_l_max              29
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3967
_reflns_number_gt                       3584
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0439
_refine_ls_R_factor_gt                  0.0404
_refine_ls_wR_factor_ref                0.1141
_refine_ls_goodness_of_fit_ref          1.053
_refine_ls_restrained_S_all             1.053
_refine_ls_number_reflns                3967
_refine_ls_number_parameters            254
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0685P)²+0.5445P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.307
_refine_diff_density_min                -0.239
_refine_diff_density_rms                0.052
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C9 0.34149(15) 0.64483(11) 0.12989(9) 0.0167(2) Uani d 1 . . C
C4 0.34921(16) 0.71295(11) 0.08035(9) 0.0180(2) Uani d 1 . . C
H4 0.4121 0.6794 0.0778 0.022 Uiso calc 1 . . H
C5 0.26245(16) 0.83109(11) 0.03478(9) 0.0181(2) Uani d 1 . . C
C6 0.16506(16) 0.87981(11) 0.03687(9) 0.0192(2) Uani d 1 . . C
H6 0.107 0.9588 0.0064 0.023 Uiso calc 1 . . H
C7 0.15508(15) 0.81048(11) 0.08422(9) 0.0173(2) Uani d 1 . . C
H7 0.0887 0.8428 0.0847 0.021 Uiso calc 1 . . H
C8 0.24354(15) 0.69228(11) 0.13150(8) 0.0154(2) Uani d 1 . . C
C1 0.23821(15) 0.62224(11) 0.18806(9) 0.0151(2) Uani d 1 . . C
H1 0.1146 0.6296 0.1454 0.018 Uiso calc 1 . . H
C2 0.32832(17) 0.42812(11) 0.16877(10) 0.0197(2) Uani d 1 . . C
H2A 0.218 0.405 0.0959 0.024 Uiso calc 1 . . H
H2B 0.3975 0.3502 0.208 0.024 Uiso calc 1 . . H
C3 0.43843(17) 0.51923(12) 0.18273(10) 0.0205(2) Uani d 1 . . C
H3A 0.5557 0.5338 0.2563 0.025 Uiso calc 1 . . H
H3B 0.4587 0.481 0.1537 0.025 Uiso calc 1 . . H
C11 0.21179(14) 0.40402(11) 0.21437(8) 0.0157(2) Uani d 1 . . C
C12 0.20448(15) 0.27032(11) 0.20182(9) 0.0175(2) Uani d 1 . . C
H12 0.2395 0.2358 0.1821 0.021 Uiso calc 1 . . H
C13 0.14563(16) 0.19062(11) 0.21872(9) 0.0189(2) Uani d 1 . . C
C14 0.08905(16) 0.23803(12) 0.24581(9) 0.0197(2) Uani d 1 . . C
C15 0.08961(16) 0.36873(12) 0.25564(9) 0.0202(2) Uani d 1 . . C
H15 0.0491 0.4017 0.2725 0.024 Uiso calc 1 . . H
C16 0.15056(16) 0.45120(11) 0.24041(9) 0.0188(2) Uani d 1 . . C
H16 0.151 0.5393 0.2475 0.023 Uiso calc 1 . . H
C17 0.36552(15) 0.69098(11) 0.29149(9) 0.0149(2) Uani d 1 . . C
C18 0.55086(16) 0.66322(11) 0.37941(9) 0.0182(2) Uani d 1 . . C
H18 0.5988 0.6003 0.3773 0.022 Uiso calc 1 . . H
C19 0.66095(15) 0.73131(12) 0.46926(9) 0.0201(2) Uani d 1 . . C
C20 0.59920(16) 0.82502(11) 0.47833(9) 0.0201(2) Uani d 1 . . C
H20 0.6767 0.8696 0.54 0.024 Uiso calc 1 . . H
C21 0.41454(16) 0.84833(11) 0.38970(9) 0.0186(2) Uani d 1 . . C
C22 0.29666(15) 0.78448(11) 0.29681(9) 0.0164(2) Uani d 1 . . C
H22 0.1734 0.8037 0.2388 0.02 Uiso calc 1 . . H
C10 0.36521(18) 0.86023(14) -0.01582(10) 0.0257(3) Uani d 1 . . C
H10A 0.3562 0.9207 -0.052 0.039 Uiso calc 1 . . H
H10B 0.318 0.7787 -0.0506 0.039 Uiso calc 1 . . H
H10C 0.4901 0.8506 0.0543 0.039 Uiso calc 1 . . H
N1 0.28099(13) 0.48519(9) 0.20352(8) 0.0165(2) Uani d 1 . . N
O1 0.26318(12) 0.90573(9) -0.01450(7) 0.0225(2) Uani d 1 . . O
F1 0.14272(10) 0.06292(7) 0.20750(6) 0.02572(19) Uani d 1 . . F
F2 0.03188(10) 0.15588(7) 0.26155(6) 0.02517(18) Uani d 1 . . F
F3 0.84151(10) 0.70554(8) 0.55424(6) 0.0300(2) Uani d 1 . . F
F4 0.34640(10) 0.93732(7) 0.39504(6) 0.02634(19) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C9 C4 . 1.3961(16) ?
C9 C8 . 1.3891(16) ?
C9 C3 . 1.4987(16) ?
C4 H4 . 0.93 ?
C4 C5 . 1.3903(17) ?
C5 C6 . 1.3955(17) ?
C5 O1 . 1.3639(14) ?
C6 H6 . 0.93 ?
C6 C7 . 1.3818(16) ?
C7 H7 . 0.93 ?
C7 C8 . 1.3984(16) ?
C8 C1 . 1.5211(15) ?
C1 H1 . 0.98 ?
C1 C17 . 1.5348(16) ?
C1 N1 . 1.4650(14) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C2 C3 . 1.5141(17) ?
C2 N1 . 1.4616(14) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C11 C12 . 1.4082(15) ?
C11 C16 . 1.4081(15) ?
C11 N1 . 1.3921(14) ?
C12 H12 . 0.93 ?
C12 C13 . 1.3760(16) ?
C13 C14 . 1.3755(17) ?
C13 F1 . 1.3482(13) ?
C14 C15 . 1.3779(17) ?
C14 F2 . 1.3561(13) ?
C15 H15 . 0.93 ?
C15 C16 . 1.3874(16) ?
C16 H16 . 0.93 ?
C17 C18 . 1.3962(16) ?
C17 C22 . 1.3903(15) ?
C18 H18 . 0.93 ?
C18 C19 . 1.3771(17) ?
C19 C20 . 1.3793(17) ?
C19 F3 . 1.3574(14) ?
C20 H20 . 0.93 ?
C20 C21 . 1.3828(17) ?
C21 C22 . 1.3814(16) ?
C21 F4 . 1.3514(13) ?
C22 H22 . 0.93 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C10 O1 . 1.4267(15) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C4 C9 C3 121.11(10) . . ?
C8 C9 C4 120.59(11) . . ?
C8 C9 C3 118.30(10) . . ?
C9 C4 H4 120.1 . . ?
C5 C4 C9 119.75(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.93(11) . . ?
O1 C5 C4 124.39(11) . . ?
O1 C5 C6 115.67(10) . . ?
C5 C6 H6 120 . . ?
C7 C6 C5 119.90(11) . . ?
C7 C6 H6 120 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.78(11) . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.02(10) . . ?
C9 C8 C1 121.63(10) . . ?
C7 C8 C1 119.28(10) . . ?
C8 C1 H1 107.6 . . ?
C8 C1 C17 108.76(9) . . ?
C17 C1 H1 107.6 . . ?
N1 C1 C8 113.44(9) . . ?
N1 C1 H1 107.6 . . ?
N1 C1 C17 111.65(9) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N1 C2 C3 111.85(10) . . ?
C9 C3 C2 110.62(10) . . ?
C9 C3 H3A 109.5 . . ?
C9 C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C16 C11 C12 117.47(10) . . ?
N1 C11 C12 120.74(10) . . ?
N1 C11 C16 121.78(10) . . ?
C11 C12 H12 120 . . ?
C13 C12 C11 120.08(11) . . ?
C13 C12 H12 120 . . ?
C14 C13 C12 121.74(11) . . ?
F1 C13 C12 118.61(11) . . ?
F1 C13 C14 119.65(11) . . ?
C13 C14 C15 119.48(11) . . ?
F2 C14 C13 119.71(11) . . ?
F2 C14 C15 120.81(11) . . ?
C14 C15 H15 120 . . ?
C14 C15 C16 119.98(11) . . ?
C16 C15 H15 120 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.21(11) . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C1 120.49(10) . . ?
C22 C17 C1 119.72(10) . . ?
C22 C17 C18 119.76(11) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.40(11) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C20 123.99(11) . . ?
F3 C19 C18 118.34(11) . . ?
F3 C19 C20 117.67(11) . . ?
C19 C20 H20 122.2 . . ?
C19 C20 C21 115.62(11) . . ?
C21 C20 H20 122.2 . . ?
C22 C21 C20 123.40(11) . . ?
F4 C21 C20 118.01(11) . . ?
F4 C21 C22 118.59(10) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 C17 118.82(10) . . ?
C21 C22 H22 120.6 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C2 N1 C1 120.74(9) . . ?
C11 N1 C1 117.48(9) . . ?
C11 N1 C2 117.54(9) . . ?
C5 O1 C10 117.11(10) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C9 C4 C5 C6 -1.31(17) . . . . ?
C9 C4 C5 O1 179.32(11) . . . . ?
C9 C8 C1 C17 102.63(12) . . . . ?
C9 C8 C1 N1 -22.26(15) . . . . ?
C4 C9 C8 C7 -1.06(17) . . . . ?
C4 C9 C8 C1 -177.89(10) . . . . ?
C4 C9 C3 C2 -143.60(11) . . . . ?
C4 C5 C6 C7 -0.02(17) . . . . ?
C4 C5 O1 C10 -2.11(17) . . . . ?
C5 C6 C7 C8 0.82(18) . . . . ?
C6 C5 O1 C10 178.50(10) . . . . ?
C6 C7 C8 C9 -0.28(17) . . . . ?
C6 C7 C8 C1 176.62(10) . . . . ?
C7 C8 C1 C17 -74.19(13) . . . . ?
C7 C8 C1 N1 160.92(10) . . . . ?
C8 C9 C4 C5 1.85(17) . . . . ?
C8 C9 C3 C2 36.51(15) . . . . ?
C8 C1 C17 C18 -84.30(12) . . . . ?
C8 C1 C17 C22 93.67(12) . . . . ?
C8 C1 N1 C2 1.68(14) . . . . ?
C8 C1 N1 C11 -154.63(10) . . . . ?
C1 C17 C18 C19 177.23(10) . . . . ?
C1 C17 C22 C21 -177.81(10) . . . . ?
C3 C9 C4 C5 -178.03(11) . . . . ?
C3 C9 C8 C7 178.83(10) . . . . ?
C3 C9 C8 C1 2.00(16) . . . . ?
C3 C2 N1 C1 36.15(14) . . . . ?
C3 C2 N1 C11 -167.56(10) . . . . ?
C11 C12 C13 C14 1.41(17) . . . . ?
C11 C12 C13 F1 -179.06(10) . . . . ?
C12 C11 C16 C15 1.56(17) . . . . ?
C12 C11 N1 C1 163.00(10) . . . . ?
C12 C11 N1 C2 5.92(16) . . . . ?
C12 C13 C14 C15 0.51(18) . . . . ?
C12 C13 C14 F2 179.90(10) . . . . ?
C13 C14 C15 C16 -1.36(18) . . . . ?
C14 C15 C16 C11 0.30(18) . . . . ?
C16 C11 C12 C13 -2.39(16) . . . . ?
C16 C11 N1 C1 -18.46(15) . . . . ?
C16 C11 N1 C2 -175.54(10) . . . . ?
C17 C1 N1 C2 -121.64(11) . . . . ?
C17 C1 N1 C11 82.05(12) . . . . ?
C17 C18 C19 C20 0.63(18) . . . . ?
C17 C18 C19 F3 -179.05(10) . . . . ?
C18 C17 C22 C21 0.17(17) . . . . ?
C18 C19 C20 C21 0.06(18) . . . . ?
C19 C20 C21 C22 -0.68(18) . . . . ?
C19 C20 C21 F4 178.60(10) . . . . ?
C20 C21 C22 C17 0.57(18) . . . . ?
C22 C17 C18 C19 -0.74(17) . . . . ?
N1 C1 C17 C18 41.64(14) . . . . ?
N1 C1 C17 C22 -140.40(10) . . . . ?
N1 C2 C3 C9 -54.50(13) . . . . ?
N1 C11 C12 C13 176.21(10) . . . . ?
N1 C11 C16 C15 -177.02(11) . . . . ?
O1 C5 C6 C7 179.41(10) . . . . ?
F1 C13 C14 C15 -179.01(11) . . . . ?
F1 C13 C14 F2 0.38(16) . . . . ?
F2 C14 C15 C16 179.25(10) . . . . ?
F3 C19 C20 C21 179.75(10) . . . . ?
F4 C21 C22 C17 -178.70(10) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-31
_database_code_depnum_ccdc_archive 'CCDC 1540727'
 
_audit_creation_date                    2020-03-09T09:17:08-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M          'P -1'
_symmetry_space_group_name_Hall         '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                          11.13700(10)
_cell_length_b                          11.8983(2)
_cell_length_c                          15.127
_cell_angle_alpha                       73.675(12)
_cell_angle_beta                        71.730(13)
_cell_angle_gamma                       72.936(11)
_cell_volume                            1779.8(2)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4585
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              needle
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.35
_exptl_crystal_size_mid                 0.22
_exptl_crystal_size_min                 0.15
_exptl_crystal_density_diffrn           1.446
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.117
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.923
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100 #373.3
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   18292
_diffrn_reflns_av_R_equivalents         0.0264
_diffrn_reflns_theta_min                3.071
_diffrn_reflns_theta_max                27.494
_diffrn_reflns_theta_full               26
_diffrn_measured_fraction_theta_max
                                        0.994
_diffrn_measured_fraction_theta_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_full
                                        0.996
_diffrn_reflns_Laue_measured_fraction_max
                                        0.994
_diffrn_reflns_point_group_measured_fraction_full
                                        0.996
_diffrn_reflns_point_group_measured_fraction_max
                                        0.994
_diffrn_reflns_limit_h_min              -14
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min              -15
_diffrn_reflns_limit_k_max              15
_diffrn_reflns_limit_l_min              -19
_diffrn_reflns_limit_l_max              19
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    8136
_reflns_number_gt                       6683
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0529
_refine_ls_R_factor_gt                  0.0427
_refine_ls_wR_factor_ref                0.1187
_refine_ls_goodness_of_fit_ref          1.047
_refine_ls_restrained_S_all             1.047
_refine_ls_number_reflns                8136
_refine_ls_number_parameters            507
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0632P)²+0.4499P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.288
_refine_diff_density_min                -0.226
_refine_diff_density_rms                0.05
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.46884(7) 0.17466(7) 0.42907(6) 0.02709(19) Uani d 1 . . F
F3 -0.28616(8) 0.27427(7) 0.41457(6) 0.02729(19) Uani d 1 . . F
F7 0.19304(8) 0.80497(8) 0.10251(7) 0.0306(2) Uani d 1 . . F
F2 0.13307(8) -0.03111(7) 0.52517(6) 0.0282(2) Uani d 1 . . F
F4 -0.29308(9) 0.17869(8) 0.27652(7) 0.0367(2) Uani d 1 . . F
F8 0.01415(9) 0.94100(8) 0.21589(8) 0.0414(2) Uani d 1 . . F
F6 0.99696(9) 0.72274(10) 0.06591(7) 0.0423(3) Uani d 1 . . F
F5 0.64283(10) 1.04325(9) 0.01535(7) 0.0416(2) Uani d 1 . . F
O2 0.31382(10) 0.26210(9) 0.11196(7) 0.0271(2) Uani d 1 . . O
O1 -0.43766(10) 0.84618(9) 0.36627(8) 0.0276(2) Uani d 1 . . O
N1 0.04437(10) 0.39220(10) 0.39888(8) 0.0197(2) Uani d 1 . . N
N2 0.57389(11) 0.64721(10) 0.15105(8) 0.0220(2) Uani d 1 . . N
C18 -0.18899(13) 0.27892(12) 0.33353(10) 0.0217(3) Uani d 1 . . C
C13 0.34214(13) 0.17371(12) 0.44325(9) 0.0213(3) Uani d 1 . . C
C11 0.12860(12) 0.28560(11) 0.42717(9) 0.0186(3) Uani d 1 . . C
C30 0.40677(13) 0.56911(12) 0.12729(9) 0.0207(3) Uani d 1 . . C
C12 0.25928(13) 0.28250(12) 0.41978(9) 0.0198(3) Uani d 1 . . C
H12 0.289 0.3532 0.3993 0.024 Uiso calc 1 . . H
C23 0.44605(13) 0.68061(12) 0.12990(10) 0.0207(3) Uani d 1 . . C
H23 0.4552 0.7315 0.0659 0.025 Uiso calc 1 . . H
C17 -0.08853(12) 0.33155(11) 0.32399(10) 0.0198(3) Uani d 1 . . C
C16 0.08838(13) 0.17602(12) 0.46298(9) 0.0202(3) Uani d 1 . . C
H16 0.0033 0.1737 0.4692 0.024 Uiso calc 1 . . H
C14 0.30664(13) 0.06466(12) 0.47878(10) 0.0231(3) Uani d 1 . . C
H14 0.3646 -0.0073 0.4947 0.028 Uiso calc 1 . . H
C29 0.34356(13) 0.57029(13) 0.06050(10) 0.0229(3) Uani d 1 . . C
H29 0.3227 0.6409 0.0169 0.027 Uiso calc 1 . . H
C26 0.41170(13) 0.35680(12) 0.18762(10) 0.0227(3) Uani d 1 . . C
H26 0.4366 0.2851 0.2289 0.027 Uiso calc 1 . . H
C5 -0.34723(13) 0.73947(12) 0.37396(10) 0.0219(3) Uani d 1 . . C
C39 0.34210(13) 0.75568(12) 0.19863(10) 0.0221(3) Uani d 1 . . C
C22 0.00916(14) 0.33086(13) 0.23946(10) 0.0259(3) Uani d 1 . . C
H22 0.0792 0.3636 0.2311 0.031 Uiso calc 1 . . H
C15 0.17699(13) 0.07223(12) 0.48861(10) 0.0221(3) Uani d 1 . . C
C8 -0.17867(12) 0.51318(12) 0.39762(9) 0.0191(3) Uani d 1 . . C
C7 -0.31007(13) 0.52846(12) 0.44581(10) 0.0208(3) Uani d 1 . . C
H7 -0.3414 0.4627 0.4862 0.025 Uiso calc 1 . . H
C31 0.43907(13) 0.46212(12) 0.19164(9) 0.0215(3) Uani d 1 . . C
C40 0.22214(14) 0.81533(12) 0.17965(10) 0.0246(3) Uani d 1 . . C
C1 -0.08782(12) 0.38903(11) 0.40326(9) 0.0191(3) Uani d 1 . . C
H1 -0.1213 0.3386 0.4646 0.023 Uiso calc 1 . . H
C28 0.31173(13) 0.46695(13) 0.05863(10) 0.0234(3) Uani d 1 . . C
H28 0.2669 0.4691 0.0154 0.028 Uiso calc 1 . . H
C27 0.34705(13) 0.35961(12) 0.12165(10) 0.0230(3) Uani d 1 . . C
C33 0.65565(13) 0.72608(13) 0.11377(9) 0.0232(3) Uani d 1 . . C
C9 -0.13198(13) 0.61279(12) 0.34006(9) 0.0207(3) Uani d 1 . . C
C25 0.50974(14) 0.46581(13) 0.26033(10) 0.0242(3) Uani d 1 . . C
H25A 0.5437 0.3847 0.2917 0.029 Uiso calc 1 . . H
H25B 0.4505 0.5089 0.3086 0.029 Uiso calc 1 . . H
C6 -0.39428(13) 0.64033(13) 0.43409(10) 0.0234(3) Uani d 1 . . C
H6 -0.4816 0.6494 0.4661 0.028 Uiso calc 1 . . H
C4 -0.21592(13) 0.72644(12) 0.32834(10) 0.0221(3) Uani d 1 . . C
H4 -0.184 0.7929 0.2902 0.026 Uiso calc 1 . . H
C19 -0.19259(14) 0.22925(12) 0.26211(11) 0.0258(3) Uani d 1 . . C
C24 0.62017(14) 0.52843(13) 0.20640(10) 0.0248(3) Uani d 1 . . C
H24A 0.6614 0.5369 0.2512 0.03 Uiso calc 1 . . H
H24B 0.6845 0.4796 0.1639 0.03 Uiso calc 1 . . H
C44 0.36475(14) 0.77320(13) 0.27875(10) 0.0267(3) Uani d 1 . . C
H44 0.4441 0.7354 0.2933 0.032 Uiso calc 1 . . H
C34 0.78936(14) 0.68471(14) 0.10924(10) 0.0265(3) Uani d 1 . . C
H34 0.8241 0.604 0.1312 0.032 Uiso calc 1 . . H
C3 0.01079(13) 0.59413(13) 0.29244(11) 0.0258(3) Uani d 1 . . C
H3A 0.0364 0.6702 0.2747 0.031 Uiso calc 1 . . H
H3B 0.0282 0.5651 0.2348 0.031 Uiso calc 1 . . H
C38 0.60756(14) 0.84923(13) 0.08051(10) 0.0261(3) Uani d 1 . . C
H38 0.5199 0.8795 0.0827 0.031 Uiso calc 1 . . H
C20 -0.09745(15) 0.23120(13) 0.17808(11) 0.0292(3) Uani d 1 . . C
H20 -0.1014 0.1991 0.1299 0.035 Uiso calc 1 . . H
C2 0.09023(13) 0.50396(12) 0.35821(11) 0.0246(3) Uani d 1 . . C
H2A 0.1803 0.4854 0.3228 0.03 Uiso calc 1 . . H
H2B 0.0861 0.54 0.4095 0.03 Uiso calc 1 . . H
C41 0.12922(14) 0.88704(13) 0.23847(12) 0.0296(3) Uani d 1 . . C
C42 0.15244(15) 0.90402(14) 0.31756(11) 0.0328(3) Uani d 1 . . C
H42 0.0901 0.953 0.3563 0.039 Uiso calc 1 . . H
C21 0.00438(15) 0.28235(14) 0.16728(11) 0.0304(3) Uani d 1 . . C
H21 0.0702 0.2843 0.1113 0.037 Uiso calc 1 . . H
C43 0.27190(16) 0.84566(14) 0.33774(11) 0.0331(3) Uani d 1 . . C
H43 0.2898 0.8551 0.3909 0.04 Uiso calc 1 . . H
C10 -0.39253(16) 0.94863(13) 0.30472(11) 0.0310(3) Uani d 1 . . C
H10A -0.357 0.9347 0.2411 0.046 Uiso calc 1 . . H
H10B -0.3266 0.9623 0.3263 0.046 Uiso calc 1 . . H
H10C -0.4636 1.0178 0.3053 0.046 Uiso calc 1 . . H
C35 0.86761(14) 0.76650(16) 0.07156(11) 0.0312(3) Uani d 1 . . C
C37 0.69316(16) 0.92398(14) 0.04468(11) 0.0302(3) Uani d 1 . . C
C36 0.82489(16) 0.88721(16) 0.03805(11) 0.0340(4) Uani d 1 . . C
H36 0.8802 0.94 0.0129 0.041 Uiso calc 1 . . H
C32 0.34448(17) 0.15063(13) 0.17612(11) 0.0330(3) Uani d 1 . . C
H32A 0.3133 0.0909 0.1637 0.049 Uiso calc 1 . . H
H32B 0.3039 0.1606 0.2404 0.049 Uiso calc 1 . . H
H32C 0.4368 0.1254 0.1674 0.049 Uiso calc 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C13 . 1.3621(15) ?
F3 C18 . 1.3573(16) ?
F7 C40 . 1.3502(17) ?
F2 C15 . 1.3631(15) ?
F4 C19 . 1.3529(16) ?
F8 C41 . 1.3563(18) ?
F6 C35 . 1.3643(18) ?
F5 C37 . 1.3639(18) ?
O2 C27 . 1.3733(17) ?
O2 C32 . 1.4269(18) ?
O1 C5 . 1.3711(16) ?
O1 C10 . 1.4260(18) ?
N1 C11 . 1.3857(16) ?
N1 C1 . 1.4639(16) ?
N1 C2 . 1.4661(17) ?
N2 C23 . 1.4729(17) ?
N2 C33 . 1.3820(18) ?
N2 C24 . 1.4636(17) ?
C18 C17 . 1.3870(19) ?
C18 C19 . 1.385(2) ?
C13 C12 . 1.3780(19) ?
C13 C14 . 1.3801(19) ?
C11 C12 . 1.4145(18) ?
C11 C16 . 1.4098(18) ?
C30 C23 . 1.5276(18) ?
C30 C29 . 1.3960(19) ?
C30 C31 . 1.3971(19) ?
C12 H12 . 0.93 ?
C23 H23 . 0.98 ?
C23 C39 . 1.5426(19) ?
C17 C22 . 1.3955(19) ?
C17 C1 . 1.5415(18) ?
C16 H16 . 0.93 ?
C16 C15 . 1.3801(18) ?
C14 H14 . 0.93 ?
C14 C15 . 1.3826(19) ?
C29 H29 . 0.93 ?
C29 C28 . 1.386(2) ?
C26 H26 . 0.93 ?
C26 C31 . 1.3948(19) ?
C26 C27 . 1.390(2) ?
C5 C6 . 1.398(2) ?
C5 C4 . 1.390(2) ?
C39 C40 . 1.393(2) ?
C39 C44 . 1.393(2) ?
C22 H22 . 0.93 ?
C22 C21 . 1.392(2) ?
C8 C7 . 1.3985(18) ?
C8 C1 . 1.5229(18) ?
C8 C9 . 1.3895(18) ?
C7 H7 . 0.93 ?
C7 C6 . 1.3862(19) ?
C31 C25 . 1.5032(19) ?
C40 C41 . 1.386(2) ?
C1 H1 . 0.98 ?
C28 H28 . 0.93 ?
C28 C27 . 1.397(2) ?
C33 C34 . 1.410(2) ?
C33 C38 . 1.407(2) ?
C9 C4 . 1.4005(18) ?
C9 C3 . 1.5037(19) ?
C25 H25A . 0.97 ?
C25 H25B . 0.97 ?
C25 C24 . 1.5167(19) ?
C6 H6 . 0.93 ?
C4 H4 . 0.93 ?
C19 C20 . 1.376(2) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C44 H44 . 0.93 ?
C44 C43 . 1.393(2) ?
C34 H34 . 0.93 ?
C34 C35 . 1.381(2) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C3 C2 . 1.5227(19) ?
C38 H38 . 0.93 ?
C38 C37 . 1.377(2) ?
C20 H20 . 0.93 ?
C20 C21 . 1.384(2) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C41 C42 . 1.378(2) ?
C42 H42 . 0.93 ?
C42 C43 . 1.392(2) ?
C21 H21 . 0.93 ?
C43 H43 . 0.93 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C35 C36 . 1.374(2) ?
C37 C36 . 1.382(2) ?
C36 H36 . 0.93 ?
C32 H32A . 0.96 ?
C32 H32B . 0.96 ?
C32 H32C . 0.96 ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C27 O2 C32 117.60(11) . . ?
C5 O1 C10 116.76(11) . . ?
C11 N1 C1 118.68(11) . . ?
C11 N1 C2 120.39(11) . . ?
C1 N1 C2 120.74(11) . . ?
C33 N2 C23 119.94(11) . . ?
C33 N2 C24 118.72(11) . . ?
C24 N2 C23 121.23(11) . . ?
F3 C18 C17 120.04(12) . . ?
F3 C18 C19 118.45(12) . . ?
C19 C18 C17 121.50(13) . . ?
F1 C13 C12 117.02(12) . . ?
F1 C13 C14 117.99(12) . . ?
C12 C13 C14 124.99(12) . . ?
N1 C11 C12 121.03(12) . . ?
N1 C11 C16 121.55(12) . . ?
C16 C11 C12 117.41(12) . . ?
C29 C30 C23 121.85(12) . . ?
C29 C30 C31 119.27(12) . . ?
C31 C30 C23 118.84(12) . . ?
C13 C12 C11 119.34(12) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N2 C23 C30 110.50(11) . . ?
N2 C23 H23 107.1 . . ?
N2 C23 C39 111.98(11) . . ?
C30 C23 H23 107.1 . . ?
C30 C23 C39 112.70(11) . . ?
C39 C23 H23 107.1 . . ?
C18 C17 C22 116.76(13) . . ?
C18 C17 C1 120.77(12) . . ?
C22 C17 C1 122.47(12) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 119.08(12) . . ?
C15 C16 H16 120.5 . . ?
C13 C14 H14 123.1 . . ?
C13 C14 C15 113.83(12) . . ?
C15 C14 H14 123.1 . . ?
C30 C29 H29 119.8 . . ?
C28 C29 C30 120.47(13) . . ?
C28 C29 H29 119.8 . . ?
C31 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C27 C26 C31 119.67(13) . . ?
O1 C5 C6 115.57(12) . . ?
O1 C5 C4 124.34(12) . . ?
C4 C5 C6 120.08(12) . . ?
C40 C39 C23 120.63(12) . . ?
C40 C39 C44 116.69(13) . . ?
C44 C39 C23 122.58(12) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.60(13) . . ?
C21 C22 H22 119.2 . . ?
F2 C15 C16 117.10(12) . . ?
F2 C15 C14 117.68(12) . . ?
C16 C15 C14 125.22(13) . . ?
C7 C8 C1 121.25(12) . . ?
C9 C8 C7 119.09(12) . . ?
C9 C8 C1 119.59(11) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.86(12) . . ?
C6 C7 H7 119.6 . . ?
C30 C31 C25 116.80(12) . . ?
C26 C31 C30 120.43(13) . . ?
C26 C31 C25 122.69(12) . . ?
F7 C40 C39 120.57(13) . . ?
F7 C40 C41 117.84(13) . . ?
C41 C40 C39 121.59(14) . . ?
N1 C1 C17 110.95(10) . . ?
N1 C1 C8 112.36(10) . . ?
N1 C1 H1 107.8 . . ?
C17 C1 H1 107.8 . . ?
C8 C1 C17 109.96(10) . . ?
C8 C1 H1 107.8 . . ?
C29 C28 H28 120 . . ?
C29 C28 C27 119.96(13) . . ?
C27 C28 H28 120 . . ?
O2 C27 C26 124.75(13) . . ?
O2 C27 C28 115.13(12) . . ?
C26 C27 C28 120.12(13) . . ?
N2 C33 C34 120.47(13) . . ?
N2 C33 C38 120.98(13) . . ?
C38 C33 C34 118.55(13) . . ?
C8 C9 C4 120.53(12) . . ?
C8 C9 C3 117.75(12) . . ?
C4 C9 C3 121.72(12) . . ?
C31 C25 H25A 109.8 . . ?
C31 C25 H25B 109.8 . . ?
C31 C25 C24 109.15(11) . . ?
H25A C25 H25B 108.3 . . ?
C24 C25 H25A 109.8 . . ?
C24 C25 H25B 109.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.66(12) . . ?
C7 C6 H6 120.2 . . ?
C5 C4 C9 119.71(12) . . ?
C5 C4 H4 120.1 . . ?
C9 C4 H4 120.1 . . ?
F4 C19 C18 118.32(13) . . ?
F4 C19 C20 120.22(13) . . ?
C20 C19 C18 121.46(13) . . ?
N2 C24 C25 111.37(11) . . ?
N2 C24 H24A 109.4 . . ?
N2 C24 H24B 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108 . . ?
C39 C44 H44 119.1 . . ?
C43 C44 C39 121.88(14) . . ?
C43 C44 H44 119.1 . . ?
C33 C34 H34 120.7 . . ?
C35 C34 C33 118.61(14) . . ?
C35 C34 H34 120.7 . . ?
C9 C3 H3A 109.4 . . ?
C9 C3 H3B 109.4 . . ?
C9 C3 C2 111.02(11) . . ?
H3A C3 H3B 108 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C33 C38 H38 120.7 . . ?
C37 C38 C33 118.57(14) . . ?
C37 C38 H38 120.7 . . ?
C19 C20 H20 121 . . ?
C19 C20 C21 118.06(14) . . ?
C21 C20 H20 121 . . ?
N1 C2 C3 112.56(11) . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
F8 C41 C40 118.12(14) . . ?
F8 C41 C42 120.52(14) . . ?
C42 C41 C40 121.35(14) . . ?
C41 C42 H42 121 . . ?
C41 C42 C43 118.06(14) . . ?
C43 C42 H42 121 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.60(14) . . ?
C20 C21 H21 119.7 . . ?
C44 C43 H43 119.8 . . ?
C42 C43 C44 120.42(15) . . ?
C42 C43 H43 119.8 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F6 C35 C34 116.99(15) . . ?
F6 C35 C36 118.23(14) . . ?
C36 C35 C34 124.76(15) . . ?
F5 C37 C38 117.06(14) . . ?
F5 C37 C36 118.10(13) . . ?
C38 C37 C36 124.83(15) . . ?
C35 C36 C37 114.67(14) . . ?
C35 C36 H36 122.7 . . ?
C37 C36 H36 122.7 . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C13 C12 C11 175.88(11) . . . . ?
F1 C13 C14 C15 -178.53(11) . . . . ?
F3 C18 C17 C22 178.77(11) . . . . ?
F3 C18 C17 C1 -2.05(19) . . . . ?
F3 C18 C19 F4 0.15(19) . . . . ?
F3 C18 C19 C20 179.81(12) . . . . ?
F7 C40 C41 F8 0.95(19) . . . . ?
F7 C40 C41 C42 -178.75(13) . . . . ?
F4 C19 C20 C21 -179.06(14) . . . . ?
F8 C41 C42 C43 179.50(13) . . . . ?
F6 C35 C36 C37 178.84(13) . . . . ?
F5 C37 C36 C35 178.15(13) . . . . ?
O1 C5 C6 C7 179.57(12) . . . . ?
O1 C5 C4 C9 -179.14(12) . . . . ?
N1 C11 C12 C13 -176.12(12) . . . . ?
N1 C11 C16 C15 178.92(12) . . . . ?
N2 C23 C39 C40 167.56(12) . . . . ?
N2 C23 C39 C44 -8.71(18) . . . . ?
N2 C33 C34 C35 -179.93(13) . . . . ?
N2 C33 C38 C37 179.53(13) . . . . ?
C18 C17 C22 C21 1.5(2) . . . . ?
C18 C17 C1 N1 156.02(12) . . . . ?
C18 C17 C1 C8 -79.07(15) . . . . ?
C18 C19 C20 C21 1.3(2) . . . . ?
C13 C14 C15 F2 -178.66(11) . . . . ?
C13 C14 C15 C16 2.4(2) . . . . ?
C11 N1 C1 C17 -72.74(14) . . . . ?
C11 N1 C1 C8 163.72(11) . . . . ?
C11 N1 C2 C3 153.95(12) . . . . ?
C11 C16 C15 F2 178.36(11) . . . . ?
C11 C16 C15 C14 -2.7(2) . . . . ?
C30 C23 C39 C40 -67.12(16) . . . . ?
C30 C23 C39 C44 116.61(14) . . . . ?
C30 C29 C28 C27 -2.3(2) . . . . ?
C30 C31 C25 C24 -47.14(16) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C11 C16 C15 -0.14(19) . . . . ?
C23 N2 C33 C34 -161.45(12) . . . . ?
C23 N2 C33 C38 19.24(19) . . . . ?
C23 N2 C24 C25 -16.97(17) . . . . ?
C23 C30 C29 C28 178.58(12) . . . . ?
C23 C30 C31 C26 -176.16(12) . . . . ?
C23 C30 C31 C25 0.74(18) . . . . ?
C23 C39 C40 F7 2.38(19) . . . . ?
C23 C39 C40 C41 -177.46(12) . . . . ?
C23 C39 C44 C43 177.05(13) . . . . ?
C17 C18 C19 F4 179.56(12) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C17 C22 C21 C20 -1.0(2) . . . . ?
C16 C11 C12 C13 2.95(19) . . . . ?
C14 C13 C12 C11 -3.4(2) . . . . ?
C29 C30 C23 N2 -140.96(13) . . . . ?
C29 C30 C23 C39 92.92(15) . . . . ?
C29 C30 C31 C26 1.73(19) . . . . ?
C29 C30 C31 C25 178.63(12) . . . . ?
C29 C28 C27 O2 -178.31(12) . . . . ?
C29 C28 C27 C26 1.4(2) . . . . ?
C26 C31 C25 C24 129.68(13) . . . . ?
C39 C40 C41 F8 -179.20(12) . . . . ?
C39 C40 C41 C42 1.1(2) . . . . ?
C39 C44 C43 C42 -0.4(2) . . . . ?
C22 C17 C1 N1 -24.85(17) . . . . ?
C22 C17 C1 C8 100.06(14) . . . . ?
C8 C7 C6 C5 -0.5(2) . . . . ?
C8 C9 C4 C5 -0.6(2) . . . . ?
C8 C9 C3 C2 -38.25(18) . . . . ?
C7 C8 C1 N1 -147.06(12) . . . . ?
C7 C8 C1 C17 88.84(15) . . . . ?
C7 C8 C9 C4 -1.7(2) . . . . ?
C7 C8 C9 C3 177.54(13) . . . . ?
C31 C30 C23 N2 36.87(16) . . . . ?
C31 C30 C23 C39 -89.25(15) . . . . ?
C31 C30 C29 C28 0.8(2) . . . . ?
C31 C26 C27 O2 -179.26(12) . . . . ?
C31 C26 C27 C28 1.1(2) . . . . ?
C31 C25 C24 N2 54.31(15) . . . . ?
C40 C39 C44 C43 0.6(2) . . . . ?
C40 C41 C42 C43 -0.8(2) . . . . ?
C1 N1 C11 C12 176.71(11) . . . . ?
C1 N1 C11 C16 -2.32(18) . . . . ?
C1 N1 C2 C3 -21.08(17) . . . . ?
C1 C17 C22 C21 -177.64(13) . . . . ?
C1 C8 C7 C6 -174.66(12) . . . . ?
C1 C8 C9 C4 175.29(12) . . . . ?
C1 C8 C9 C3 -5.44(19) . . . . ?
C27 C26 C31 C30 -2.7(2) . . . . ?
C27 C26 C31 C25 -179.37(12) . . . . ?
C33 N2 C23 C30 148.49(12) . . . . ?
C33 N2 C23 C39 -84.98(14) . . . . ?
C33 N2 C24 C25 166.77(12) . . . . ?
C33 C34 C35 F6 -178.25(12) . . . . ?
C33 C34 C35 C36 0.4(2) . . . . ?
C33 C38 C37 F5 -178.35(12) . . . . ?
C33 C38 C37 C36 0.4(2) . . . . ?
C9 C8 C7 C6 2.3(2) . . . . ?
C9 C8 C1 N1 35.99(17) . . . . ?
C9 C8 C1 C17 -88.10(14) . . . . ?
C9 C3 C2 N1 50.93(16) . . . . ?
C6 C5 C4 C9 2.4(2) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C4 C9 C3 C2 141.00(13) . . . . ?
C19 C18 C17 C22 -0.6(2) . . . . ?
C19 C18 C17 C1 178.55(12) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C24 N2 C23 C30 -27.72(16) . . . . ?
C24 N2 C23 C39 98.81(14) . . . . ?
C24 N2 C33 C34 14.86(19) . . . . ?
C24 N2 C33 C38 -164.45(13) . . . . ?
C44 C39 C40 F7 178.86(12) . . . . ?
C44 C39 C40 C41 -1.0(2) . . . . ?
C34 C33 C38 C37 0.2(2) . . . . ?
C34 C35 C36 C37 0.2(2) . . . . ?
C3 C9 C4 C5 -179.84(13) . . . . ?
C38 C33 C34 C35 -0.6(2) . . . . ?
C38 C37 C36 C35 -0.6(2) . . . . ?
C2 N1 C11 C12 1.58(19) . . . . ?
C2 N1 C11 C16 -177.45(12) . . . . ?
C2 N1 C1 C17 102.38(14) . . . . ?
C2 N1 C1 C8 -21.16(17) . . . . ?
C41 C42 C43 C44 0.5(2) . . . . ?
C10 O1 C5 C6 -179.45(12) . . . . ?
C10 O1 C5 C4 2.01(19) . . . . ?
C32 O2 C27 C26 1.9(2) . . . . ?
C32 O2 C27 C28 -178.41(12) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

data_6-33
_database_code_depnum_ccdc_archive 'CCDC 1540728'
 
_audit_creation_date                    2020-03-09T09:18:16-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M          'P -1'
_symmetry_space_group_name_Hall         '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                          10.6975(7)
_cell_length_b                          13.2186(4)
_cell_length_c                          13.6339(2)
_cell_angle_alpha                       68.667(14)
_cell_angle_beta                        80.428(18)
_cell_angle_gamma                       81.09(2)
_cell_volume                            1761.4(2)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4971
_cell_measurement_theta_min             3.1
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              irregular
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.3
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.1
_exptl_crystal_density_diffrn           1.461
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.118
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing 1995'
_exptl_absorpt_correction_T_min         0.945
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100 # 373.3
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   18147
_diffrn_reflns_av_R_equivalents         0.0276
_diffrn_reflns_theta_min                3.079
_diffrn_reflns_theta_max                27.505
_diffrn_reflns_theta_full               26
_diffrn_measured_fraction_theta_max
                                        0.993
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_full
                                        0.997
_diffrn_reflns_Laue_measured_fraction_max
                                        0.993
_diffrn_reflns_point_group_measured_fraction_full
                                        0.997
_diffrn_reflns_point_group_measured_fraction_max
                                        0.993
_diffrn_reflns_limit_h_min              -13
_diffrn_reflns_limit_h_max              13
_diffrn_reflns_limit_k_min              -17
_diffrn_reflns_limit_k_max              17
_diffrn_reflns_limit_l_min              -17
_diffrn_reflns_limit_l_max              17
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          difmap
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    8043
_reflns_number_gt                       6601
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0506
_refine_ls_R_factor_gt                  0.0407
_refine_ls_wR_factor_ref                0.107
_refine_ls_goodness_of_fit_ref          1.045
_refine_ls_restrained_S_all             1.045
_refine_ls_number_reflns                8043
_refine_ls_number_parameters            641
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           refall
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0523P)²+0.5918P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.294
_refine_diff_density_min                -0.233
_refine_diff_density_rms                0.05
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
F1 0.23185(8) 0.59769(7) -0.07978(7) 0.0258(2) Uani d 1 . . F
F2 -0.02012(8) 0.40619(7) 0.22791(7) 0.0263(2) Uani d 1 . . F
F3 0.29550(8) -0.03600(7) 0.40197(7) 0.0263(2) Uani d 1 . . F
F4 0.45992(9) 0.28622(7) 0.48963(7) 0.0289(2) Uani d 1 . . F
O1 0.75650(10) -0.16546(8) 0.11591(8) 0.0232(2) Uani d 1 . . O
N1 0.40150(11) 0.25182(9) 0.14688(9) 0.0181(2) Uani d 1 . . N
C1 0.37769(13) 0.14265(11) 0.22281(10) 0.0169(3) Uani d 1 . . C
H1 0.2932(16) 0.1293(13) 0.2153(12) 0.018(4) Uiso d 1 . . H
C2 0.53086(13) 0.27412(11) 0.09475(12) 0.0201(3) Uani d 1 . . C
H2A 0.5407(16) 0.2737(14) 0.0195(14) 0.024(4) Uiso d 1 . . H
H2B 0.5443(16) 0.3496(14) 0.0903(13) 0.021(4) Uiso d 1 . . H
C3 0.63111(13) 0.18923(11) 0.15582(12) 0.0192(3) Uani d 1 . . C
H3A 0.6280(15) 0.1976(13) 0.2255(13) 0.019(4) Uiso d 1 . . H
H3B 0.7169(17) 0.2038(13) 0.1154(13) 0.023(4) Uiso d 1 . . H
C4 0.69361(13) 0.00094(11) 0.14245(11) 0.0188(3) Uani d 1 . . C
H4 0.7828(17) 0.0118(13) 0.1250(13) 0.020(4) Uiso d 1 . . H
C5 0.65856(13) -0.09665(11) 0.14300(11) 0.0194(3) Uani d 1 . . C
C6 0.53106(14) -0.11764(12) 0.16892(11) 0.0216(3) Uani d 1 . . C
H6 0.5027(16) -0.1862(14) 0.1725(13) 0.025(4) Uiso d 1 . . H
C7 0.43996(14) -0.04057(12) 0.19463(11) 0.0202(3) Uani d 1 . . C
H7 0.3491(17) -0.0571(14) 0.2120(14) 0.027(4) Uiso d 1 . . H
C8 0.47422(13) 0.05656(11) 0.19456(10) 0.0172(3) Uani d 1 . . C
C9 0.60200(13) 0.07761(11) 0.16655(10) 0.0173(3) Uani d 1 . . C
C10 0.72118(17) -0.25656(13) 0.09738(14) 0.0283(3) Uani d 1 . . C
H10A 0.8004(18) -0.2939(15) 0.0758(14) 0.031(5) Uiso d 1 . . H
H10B 0.6794(17) -0.3086(15) 0.1628(15) 0.028(4) Uiso d 1 . . H
H10C 0.663(2) -0.2306(16) 0.0393(16) 0.039(5) Uiso d 1 . . H
C11 0.30319(13) 0.33405(11) 0.12324(11) 0.0173(3) Uani d 1 . . C
C12 0.18641(13) 0.32758(11) 0.19015(11) 0.0192(3) Uani d 1 . . C
H12 0.1728(17) 0.2693(15) 0.2564(14) 0.027(4) Uiso d 1 . . H
C13 0.09163(13) 0.41294(12) 0.16223(12) 0.0206(3) Uani d 1 . . C
C14 0.10193(14) 0.50569(12) 0.07353(12) 0.0212(3) Uani d 1 . . C
H14 0.0351(17) 0.5634(15) 0.0570(14) 0.027(4) Uiso d 1 . . H
C15 0.21682(14) 0.50848(11) 0.00999(11) 0.0197(3) Uani d 1 . . C
C16 0.31748(13) 0.42769(11) 0.03056(11) 0.0188(3) Uani d 1 . . C
H16 0.3947(17) 0.4355(14) -0.0214(14) 0.023(4) Uiso d 1 . . H
C17 0.37784(13) 0.13472(11) 0.33846(11) 0.0177(3) Uani d 1 . . C
C18 0.33668(13) 0.04521(11) 0.42344(11) 0.0199(3) Uani d 1 . . C
C19 0.33514(14) 0.03379(12) 0.52872(12) 0.0236(3) Uani d 1 . . C
H19 0.3053(17) -0.0325(15) 0.5842(14) 0.028(4) Uiso d 1 . . H
C20 0.37750(14) 0.11575(13) 0.55231(12) 0.0240(3) Uani d 1 . . C
H20 0.3780(16) 0.1119(14) 0.6249(15) 0.026(4) Uiso d 1 . . H
C21 0.41811(13) 0.20475(12) 0.46859(12) 0.0217(3) Uani d 1 . . C
C22 0.41838(13) 0.21701(12) 0.36329(11) 0.0195(3) Uani d 1 . . C
H22 0.4438(16) 0.2818(14) 0.3079(14) 0.022(4) Uiso d 1 . . H
F5 1.08296(9) -0.09685(7) 0.58556(7) 0.0305(2) Uani d 1 . . F
F6 1.00838(9) -0.23208(7) 0.95746(7) 0.0285(2) Uani d 1 . . F
F7 0.86180(8) 0.35375(8) 0.45248(6) 0.0272(2) Uani d 1 . . F
F8 1.27388(8) 0.33469(8) 0.64546(7) 0.0313(2) Uani d 1 . . F
O2 0.44600(9) 0.53026(8) 0.75727(8) 0.0227(2) Uani d 1 . . O
N2 0.87765(11) 0.14102(9) 0.77005(9) 0.0178(2) Uani d 1 . . N
C23 0.84684(13) 0.22671(11) 0.67014(10) 0.0166(3) Uani d 1 . . C
H23 0.8171(15) 0.1927(12) 0.6259(12) 0.015(4) Uiso d 1 . . H
C24 0.84951(14) 0.16241(12) 0.87036(11) 0.0202(3) Uani d 1 . . C
H24A 0.7726(18) 0.1264(15) 0.9136(14) 0.028(5) Uiso d 1 . . H
H24B 0.9229(17) 0.1267(14) 0.9118(14) 0.027(4) Uiso d 1 . . H
C25 0.83199(14) 0.28470(11) 0.85188(11) 0.0197(3) Uani d 1 . . C
H25A 0.9161(17) 0.3165(14) 0.8203(13) 0.023(4) Uiso d 1 . . H
H25B 0.8075(17) 0.2945(14) 0.9218(14) 0.027(4) Uiso d 1 . . H
C26 0.63470(13) 0.41581(11) 0.79649(11) 0.0188(3) Uani d 1 . . C
H26 0.6277(17) 0.4419(14) 0.8575(14) 0.028(4) Uiso d 1 . . H
C27 0.53790(13) 0.45690(11) 0.73024(11) 0.0181(3) Uani d 1 . . C
C28 0.53820(13) 0.42099(11) 0.64592(11) 0.0187(3) Uani d 1 . . C
H28 0.4708(15) 0.4456(12) 0.6001(12) 0.015(4) Uiso d 1 . . H
C29 0.63760(13) 0.34584(11) 0.62704(11) 0.0177(3) Uani d 1 . . C
H29 0.6372(16) 0.3196(13) 0.5690(13) 0.022(4) Uiso d 1 . . H
C30 0.73581(12) 0.30663(11) 0.69085(10) 0.0161(3) Uani d 1 . . C
C31 0.73196(13) 0.34010(11) 0.77775(10) 0.0172(3) Uani d 1 . . C
C32 0.33869(14) 0.56731(13) 0.69741(13) 0.0249(3) Uani d 1 . . C
H32A 0.2943(18) 0.5046(16) 0.7050(15) 0.031(5) Uiso d 1 . . H
H32B 0.2835(17) 0.6209(15) 0.7251(14) 0.029(5) Uiso d 1 . . H
H32C 0.3672(18) 0.6050(15) 0.6231(16) 0.031(5) Uiso d 1 . . H
C33 0.93310(12) 0.03982(11) 0.76984(11) 0.0177(3) Uani d 1 . . C
C34 0.98210(13) 0.02177(12) 0.67413(12) 0.0202(3) Uani d 1 . . C
H34 0.9810(17) 0.0786(14) 0.6057(14) 0.026(4) Uiso d 1 . . H
C35 1.03720(13) -0.08104(12) 0.67885(12) 0.0221(3) Uani d 1 . . C
C36 1.05114(13) -0.16891(12) 0.77155(12) 0.0228(3) Uani d 1 . . C
H36 1.0925(18) -0.2392(16) 0.7700(14) 0.031(5) Uiso d 1 . . H
C37 1.00035(13) -0.14825(11) 0.86294(11) 0.0211(3) Uani d 1 . . C
C38 0.94160(13) -0.04897(11) 0.86651(11) 0.0198(3) Uani d 1 . . C
H38 0.9024(16) -0.0446(13) 0.9358(14) 0.021(4) Uiso d 1 . . H
C39 0.96354(13) 0.28587(11) 0.60818(11) 0.0173(3) Uani d 1 . . C
C40 0.96524(13) 0.34861(11) 0.50108(11) 0.0192(3) Uani d 1 . . C
C41 1.06568(14) 0.40654(12) 0.44130(12) 0.0229(3) Uani d 1 . . C
H41 1.0592(18) 0.4500(15) 0.3677(15) 0.032(5) Uiso d 1 . . H
C42 1.17144(14) 0.40278(12) 0.48994(12) 0.0228(3) Uani d 1 . . C
H42 1.2445(18) 0.4422(15) 0.4514(14) 0.030(5) Uiso d 1 . . H
C43 1.17122(13) 0.33974(12) 0.59586(12) 0.0210(3) Uani d 1 . . C
C44 1.07166(13) 0.28047(11) 0.65557(11) 0.0196(3) Uani d 1 . . C
H44 1.0782(17) 0.2360(14) 0.7299(14) 0.027(4) Uiso d 1 . . H
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
F1 C15 . 1.3629(16) ?
F2 C13 . 1.3631(16) ?
F3 C18 . 1.3603(16) ?
F4 C21 . 1.3633(16) ?
O1 C5 . 1.3718(17) ?
O1 C10 . 1.4320(18) ?
N1 C1 . 1.4691(17) ?
N1 C2 . 1.4676(18) ?
N1 C11 . 1.3766(18) ?
C1 H1 . 0.976(17) ?
C1 C8 . 1.5272(19) ?
C1 C17 . 1.5420(18) ?
C2 H2A . 1.016(18) ?
C2 H2B . 1.009(17) ?
C2 C3 . 1.5320(19) ?
C3 H3A . 0.991(17) ?
C3 H3B . 0.996(17) ?
C3 C9 . 1.5052(19) ?
C4 H4 . 0.965(17) ?
C4 C5 . 1.395(2) ?
C4 C9 . 1.3867(19) ?
C5 C6 . 1.396(2) ?
C6 H6 . 0.981(18) ?
C6 C7 . 1.396(2) ?
C7 H7 . 1.000(18) ?
C7 C8 . 1.3884(19) ?
C8 C9 . 1.3995(19) ?
C10 H10A . 0.970(19) ?
C10 H10B . 0.992(19) ?
C10 H10C . 1.01(2) ?
C11 C12 . 1.4133(19) ?
C11 C16 . 1.4172(19) ?
C12 H12 . 0.956(18) ?
C12 C13 . 1.381(2) ?
C13 C14 . 1.377(2) ?
C14 H14 . 0.951(18) ?
C14 C15 . 1.378(2) ?
C15 C16 . 1.380(2) ?
C16 H16 . 0.987(18) ?
C17 C18 . 1.3894(19) ?
C17 C22 . 1.3961(19) ?
C18 C19 . 1.385(2) ?
C19 H19 . 0.983(18) ?
C19 C20 . 1.392(2) ?
C20 H20 . 0.973(18) ?
C20 C21 . 1.376(2) ?
C21 C22 . 1.384(2) ?
C22 H22 . 0.954(18) ?
F5 C35 . 1.3623(16) ?
F6 C37 . 1.3654(16) ?
F7 C40 . 1.3623(16) ?
F8 C43 . 1.3635(16) ?
O2 C27 . 1.3736(17) ?
O2 C32 . 1.4389(17) ?
N2 C23 . 1.4691(17) ?
N2 C24 . 1.4694(17) ?
N2 C33 . 1.3776(17) ?
C23 H23 . 0.985(16) ?
C23 C30 . 1.5242(19) ?
C23 C39 . 1.5346(19) ?
C24 H24A . 1.003(19) ?
C24 H24B . 0.999(18) ?
C24 C25 . 1.5287(19) ?
C25 H25A . 1.014(18) ?
C25 H25B . 0.995(18) ?
C25 C31 . 1.5103(19) ?
C26 H26 . 0.998(18) ?
C26 C27 . 1.4012(19) ?
C26 C31 . 1.3872(19) ?
C27 C28 . 1.394(2) ?
C28 H28 . 0.972(16) ?
C28 C29 . 1.397(2) ?
C29 H29 . 0.974(17) ?
C29 C30 . 1.3916(19) ?
C30 C31 . 1.4003(19) ?
C32 H32A . 0.98(2) ?
C32 H32B . 0.991(19) ?
C32 H32C . 0.972(19) ?
C33 C34 . 1.412(2) ?
C33 C38 . 1.4156(19) ?
C34 H34 . 0.962(18) ?
C34 C35 . 1.378(2) ?
C35 C36 . 1.382(2) ?
C36 H36 . 0.972(19) ?
C36 C37 . 1.378(2) ?
C37 C38 . 1.379(2) ?
C38 H38 . 0.986(17) ?
C39 C40 . 1.3911(19) ?
C39 C44 . 1.3963(19) ?
C40 C41 . 1.384(2) ?
C41 H41 . 0.966(19) ?
C41 C42 . 1.389(2) ?
C42 H42 . 0.975(19) ?
C42 C43 . 1.380(2) ?
C43 C44 . 1.385(2) ?
C44 H44 . 0.977(18) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C5 O1 C10 116.45(11) . . ?
C2 N1 C1 120.12(11) . . ?
C11 N1 C1 120.65(11) . . ?
C11 N1 C2 119.22(11) . . ?
N1 C1 H1 107.2(9) . . ?
N1 C1 C8 109.86(11) . . ?
N1 C1 C17 112.13(11) . . ?
C8 C1 H1 107.7(9) . . ?
C8 C1 C17 111.71(11) . . ?
C17 C1 H1 107.9(9) . . ?
N1 C2 H2A 110.4(10) . . ?
N1 C2 H2B 108.1(9) . . ?
N1 C2 C3 111.23(11) . . ?
H2A C2 H2B 107.7(13) . . ?
C3 C2 H2A 108.9(10) . . ?
C3 C2 H2B 110.4(9) . . ?
C2 C3 H3A 107.9(9) . . ?
C2 C3 H3B 108.9(10) . . ?
H3A C3 H3B 109.3(14) . . ?
C9 C3 C2 108.43(11) . . ?
C9 C3 H3A 112.3(9) . . ?
C9 C3 H3B 110.0(10) . . ?
C5 C4 H4 117.3(10) . . ?
C9 C4 H4 122.5(10) . . ?
C9 C4 C5 120.21(13) . . ?
O1 C5 C4 115.25(12) . . ?
O1 C5 C6 124.86(13) . . ?
C4 C5 C6 119.89(13) . . ?
C5 C6 H6 122.5(10) . . ?
C5 C6 C7 119.39(13) . . ?
C7 C6 H6 118.0(10) . . ?
C6 C7 H7 117.9(10) . . ?
C8 C7 C6 121.03(13) . . ?
C8 C7 H7 121.1(10) . . ?
C7 C8 C1 122.67(12) . . ?
C7 C8 C9 119.08(13) . . ?
C9 C8 C1 118.24(12) . . ?
C4 C9 C3 122.78(12) . . ?
C4 C9 C8 120.38(12) . . ?
C8 C9 C3 116.66(12) . . ?
O1 C10 H10A 105.7(11) . . ?
O1 C10 H10B 111.9(11) . . ?
O1 C10 H10C 110.4(11) . . ?
H10A C10 H10B 108.0(15) . . ?
H10A C10 H10C 110.5(16) . . ?
H10B C10 H10C 110.2(15) . . ?
N1 C11 C12 121.23(12) . . ?
N1 C11 C16 120.29(12) . . ?
C12 C11 C16 118.49(13) . . ?
C11 C12 H12 122.6(11) . . ?
C13 C12 C11 118.44(13) . . ?
C13 C12 H12 118.8(11) . . ?
F2 C13 C12 117.88(13) . . ?
F2 C13 C14 117.17(13) . . ?
C14 C13 C12 124.94(13) . . ?
C13 C14 H14 122.8(11) . . ?
C13 C14 C15 114.82(13) . . ?
C15 C14 H14 122.4(11) . . ?
F1 C15 C14 117.44(12) . . ?
F1 C15 C16 117.73(13) . . ?
C14 C15 C16 124.83(13) . . ?
C11 C16 H16 122.5(10) . . ?
C15 C16 C11 118.47(13) . . ?
C15 C16 H16 118.9(10) . . ?
C18 C17 C1 121.49(12) . . ?
C18 C17 C22 116.58(13) . . ?
C22 C17 C1 121.93(12) . . ?
F3 C18 C17 118.05(12) . . ?
F3 C18 C19 118.07(12) . . ?
C19 C18 C17 123.87(13) . . ?
C18 C19 H19 118.8(10) . . ?
C18 C19 C20 118.93(14) . . ?
C20 C19 H19 122.3(10) . . ?
C19 C20 H20 122.2(10) . . ?
C21 C20 C19 117.53(14) . . ?
C21 C20 H20 120.3(10) . . ?
F4 C21 C20 118.66(13) . . ?
F4 C21 C22 117.66(13) . . ?
C20 C21 C22 123.68(14) . . ?
C17 C22 H22 119.9(10) . . ?
C21 C22 C17 119.39(13) . . ?
C21 C22 H22 120.7(10) . . ?
C27 O2 C32 116.97(11) . . ?
C23 N2 C24 120.45(11) . . ?
C33 N2 C23 119.84(11) . . ?
C33 N2 C24 119.71(11) . . ?
N2 C23 H23 108.7(9) . . ?
N2 C23 C30 110.59(11) . . ?
N2 C23 C39 111.66(11) . . ?
C30 C23 H23 105.8(9) . . ?
C30 C23 C39 111.40(11) . . ?
C39 C23 H23 108.5(9) . . ?
N2 C24 H24A 110.3(10) . . ?
N2 C24 H24B 107.2(10) . . ?
N2 C24 C25 111.79(11) . . ?
H24A C24 H24B 106.5(14) . . ?
C25 C24 H24A 111.0(10) . . ?
C25 C24 H24B 109.8(10) . . ?
C24 C25 H25A 109.5(9) . . ?
C24 C25 H25B 108.3(10) . . ?
H25A C25 H25B 107.6(14) . . ?
C31 C25 C24 109.34(11) . . ?
C31 C25 H25A 110.3(9) . . ?
C31 C25 H25B 111.8(10) . . ?
C27 C26 H26 116.7(10) . . ?
C31 C26 H26 123.1(10) . . ?
C31 C26 C27 120.14(13) . . ?
O2 C27 C26 114.95(12) . . ?
O2 C27 C28 124.90(12) . . ?
C28 C27 C26 120.13(13) . . ?
C27 C28 H28 122.3(9) . . ?
C27 C28 C29 119.16(12) . . ?
C29 C28 H28 118.5(9) . . ?
C28 C29 H29 119.3(10) . . ?
C30 C29 C28 121.10(13) . . ?
C30 C29 H29 119.6(10) . . ?
C29 C30 C23 122.00(12) . . ?
C29 C30 C31 119.21(12) . . ?
C31 C30 C23 118.78(12) . . ?
C26 C31 C25 122.75(12) . . ?
C26 C31 C30 120.18(12) . . ?
C30 C31 C25 116.95(12) . . ?
O2 C32 H32A 109.6(11) . . ?
O2 C32 H32B 106.7(11) . . ?
O2 C32 H32C 110.0(11) . . ?
H32A C32 H32B 112.4(15) . . ?
H32A C32 H32C 110.1(16) . . ?
H32B C32 H32C 107.8(15) . . ?
N2 C33 C34 121.26(12) . . ?
N2 C33 C38 120.27(12) . . ?
C34 C33 C38 118.47(13) . . ?
C33 C34 H34 122.9(10) . . ?
C35 C34 C33 118.68(13) . . ?
C35 C34 H34 118.4(10) . . ?
F5 C35 C34 117.71(13) . . ?
F5 C35 C36 117.59(13) . . ?
C34 C35 C36 124.69(14) . . ?
C35 C36 H36 121.0(11) . . ?
C37 C36 C35 114.72(13) . . ?
C37 C36 H36 124.2(11) . . ?
F6 C37 C36 117.90(13) . . ?
F6 C37 C38 117.14(13) . . ?
C36 C37 C38 124.96(13) . . ?
C33 C38 H38 123.1(10) . . ?
C37 C38 C33 118.43(13) . . ?
C37 C38 H38 118.3(10) . . ?
C40 C39 C23 120.75(12) . . ?
C40 C39 C44 116.92(13) . . ?
C44 C39 C23 122.33(12) . . ?
F7 C40 C39 118.09(12) . . ?
F7 C40 C41 118.18(12) . . ?
C41 C40 C39 123.73(13) . . ?
C40 C41 H41 119.1(11) . . ?
C40 C41 C42 118.85(14) . . ?
C42 C41 H41 122.0(11) . . ?
C41 C42 H42 122.0(11) . . ?
C43 C42 C41 117.82(13) . . ?
C43 C42 H42 120.2(11) . . ?
F8 C43 C42 118.97(13) . . ?
F8 C43 C44 117.53(13) . . ?
C42 C43 C44 123.50(13) . . ?
C39 C44 H44 121.4(11) . . ?
C43 C44 C39 119.15(13) . . ?
C43 C44 H44 119.5(11) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
F1 C15 C16 C11 -179.63(11) . . . . ?
F2 C13 C14 C15 179.87(12) . . . . ?
F3 C18 C19 C20 179.68(12) . . . . ?
F4 C21 C22 C17 179.17(12) . . . . ?
O1 C5 C6 C7 -179.66(13) . . . . ?
N1 C1 C8 C7 -135.84(13) . . . . ?
N1 C1 C8 C9 43.52(16) . . . . ?
N1 C1 C17 C18 169.19(12) . . . . ?
N1 C1 C17 C22 -10.40(18) . . . . ?
N1 C2 C3 C9 56.24(15) . . . . ?
N1 C11 C12 C13 179.79(13) . . . . ?
N1 C11 C16 C15 -179.73(12) . . . . ?
C1 N1 C2 C3 -19.41(17) . . . . ?
C1 N1 C11 C12 18.02(19) . . . . ?
C1 N1 C11 C16 -162.07(12) . . . . ?
C1 C8 C9 C3 -6.13(18) . . . . ?
C1 C8 C9 C4 178.62(12) . . . . ?
C1 C17 C18 F3 -0.17(19) . . . . ?
C1 C17 C18 C19 179.81(13) . . . . ?
C1 C17 C22 C21 -179.10(12) . . . . ?
C2 N1 C1 C8 -28.98(16) . . . . ?
C2 N1 C1 C17 95.86(14) . . . . ?
C2 N1 C11 C12 -162.37(13) . . . . ?
C2 N1 C11 C16 17.54(19) . . . . ?
C2 C3 C9 C4 131.22(13) . . . . ?
C2 C3 C9 C8 -43.90(16) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C4 C9 C3 -173.12(13) . . . . ?
C5 C4 C9 C8 1.8(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C1 -179.63(13) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C3 173.25(12) . . . . ?
C7 C8 C9 C4 -2.0(2) . . . . ?
C8 C1 C17 C18 -66.99(16) . . . . ?
C8 C1 C17 C22 113.42(14) . . . . ?
C9 C4 C5 O1 178.74(12) . . . . ?
C9 C4 C5 C6 -0.6(2) . . . . ?
C10 O1 C5 C4 -169.26(13) . . . . ?
C10 O1 C5 C6 10.1(2) . . . . ?
C11 N1 C1 C8 150.62(12) . . . . ?
C11 N1 C1 C17 -84.53(15) . . . . ?
C11 N1 C2 C3 160.98(12) . . . . ?
C11 C12 C13 F2 -179.41(12) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C11 C16 C15 0.19(19) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 F1 179.12(12) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C16 C11 C12 C13 -0.1(2) . . . . ?
C17 C1 C8 C7 99.07(15) . . . . ?
C17 C1 C8 C9 -81.57(15) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C17 C22 C21 1.3(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 F4 179.92(12) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C20 C21 C22 C17 -1.2(2) . . . . ?
C22 C17 C18 F3 179.44(12) . . . . ?
C22 C17 C18 C19 -0.6(2) . . . . ?
F5 C35 C36 C37 -178.60(12) . . . . ?
F6 C37 C38 C33 179.31(12) . . . . ?
F7 C40 C41 C42 179.51(13) . . . . ?
F8 C43 C44 C39 178.37(12) . . . . ?
O2 C27 C28 C29 -179.92(12) . . . . ?
N2 C23 C30 C29 -137.52(13) . . . . ?
N2 C23 C30 C31 41.50(16) . . . . ?
N2 C23 C39 C40 162.99(12) . . . . ?
N2 C23 C39 C44 -17.50(18) . . . . ?
N2 C24 C25 C31 54.13(16) . . . . ?
N2 C33 C34 C35 179.62(13) . . . . ?
N2 C33 C38 C37 -178.56(12) . . . . ?
C23 N2 C24 C25 -19.53(18) . . . . ?
C23 N2 C33 C34 11.50(19) . . . . ?
C23 N2 C33 C38 -168.24(12) . . . . ?
C23 C30 C31 C25 -6.32(18) . . . . ?
C23 C30 C31 C26 177.63(12) . . . . ?
C23 C39 C40 F7 -1.55(19) . . . . ?
C23 C39 C40 C41 178.08(13) . . . . ?
C23 C39 C44 C43 -177.26(12) . . . . ?
C24 N2 C23 C30 -26.97(17) . . . . ?
C24 N2 C23 C39 97.68(14) . . . . ?
C24 N2 C33 C34 -168.61(13) . . . . ?
C24 N2 C33 C38 11.65(19) . . . . ?
C24 C25 C31 C26 134.19(14) . . . . ?
C24 C25 C31 C30 -41.75(17) . . . . ?
C26 C27 C28 C29 -1.5(2) . . . . ?
C27 C26 C31 C25 -174.04(13) . . . . ?
C27 C26 C31 C30 1.8(2) . . . . ?
C27 C28 C29 C30 -0.1(2) . . . . ?
C28 C29 C30 C23 -178.52(12) . . . . ?
C28 C29 C30 C31 2.5(2) . . . . ?
C29 C30 C31 C25 172.73(12) . . . . ?
C29 C30 C31 C26 -3.3(2) . . . . ?
C30 C23 C39 C40 -72.81(16) . . . . ?
C30 C23 C39 C44 106.70(14) . . . . ?
C31 C26 C27 O2 179.22(12) . . . . ?
C31 C26 C27 C28 0.7(2) . . . . ?
C32 O2 C27 C26 -174.62(12) . . . . ?
C32 O2 C27 C28 3.84(19) . . . . ?
C33 N2 C23 C30 152.91(12) . . . . ?
C33 N2 C23 C39 -82.43(15) . . . . ?
C33 N2 C24 C25 160.59(12) . . . . ?
C33 C34 C35 F5 179.51(12) . . . . ?
C33 C34 C35 C36 -1.5(2) . . . . ?
C34 C33 C38 C37 1.7(2) . . . . ?
C34 C35 C36 C37 2.4(2) . . . . ?
C35 C36 C37 F6 178.69(12) . . . . ?
C35 C36 C37 C38 -1.3(2) . . . . ?
C36 C37 C38 C33 -0.7(2) . . . . ?
C38 C33 C34 C35 -0.6(2) . . . . ?
C39 C23 C30 C29 97.68(15) . . . . ?
C39 C23 C30 C31 -83.30(15) . . . . ?
C39 C40 C41 C42 -0.1(2) . . . . ?
C40 C39 C44 C43 2.3(2) . . . . ?
C40 C41 C42 C43 0.8(2) . . . . ?
C41 C42 C43 F8 -179.99(13) . . . . ?
C41 C42 C43 C44 0.0(2) . . . . ?
C42 C43 C44 C39 -1.7(2) . . . . ?
C44 C39 C40 F7 178.91(12) . . . . ?
C44 C39 C40 C41 -1.5(2) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-34
_database_code_depnum_ccdc_archive 'CCDC 1540729'
 
_audit_creation_date                    2020-03-09T09:19:26-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C22 H17 F4 N O'
_chemical_formula_sum                   'C22 H17 F4 N O'
_chemical_formula_weight                387.36
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 1 21/c 1'
_symmetry_space_group_name_Hall         '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                          11.322(2)
_cell_length_b                          12.437(2)
_cell_length_c                          20.012(3)
_cell_angle_alpha                       90
_cell_angle_beta                        140.922(8)
_cell_angle_gamma                       90
_cell_volume                            1776.3(5)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4216
_cell_measurement_theta_min             3.2
_cell_measurement_theta_max             27.5
_cell_measurement_temperature           100
_exptl_crystal_description              plate
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.41
_exptl_crystal_size_mid                 0.35
_exptl_crystal_size_min                 0.16
_exptl_crystal_density_diffrn           1.448
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    800
_exptl_absorpt_coefficient_mu           0.117
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Blessing, 1995'
_exptl_absorpt_correction_T_min         0.853
_exptl_absorpt_correction_T_max         1
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_detector_area_resol_mean        13.6612
_diffrn_reflns_number                   17876
_diffrn_reflns_av_R_equivalents         0.048
_diffrn_reflns_theta_min                3.23
_diffrn_reflns_theta_max                27.519
_diffrn_reflns_theta_full               26
_diffrn_measured_fraction_theta_max
                                        0.996
_diffrn_measured_fraction_theta_full
                                        0.998
_diffrn_reflns_Laue_measured_fraction_full
                                        0.998
_diffrn_reflns_Laue_measured_fraction_max
                                        0.996
_diffrn_reflns_point_group_measured_fraction_full
                                        0.998
_diffrn_reflns_point_group_measured_fraction_max
                                        0.996
_diffrn_reflns_limit_h_min              -14
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min              -16
_diffrn_reflns_limit_k_max              16
_diffrn_reflns_limit_l_min              -25
_diffrn_reflns_limit_l_max              25
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          difmap
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    4065
_reflns_number_gt                       3208
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0704
_refine_ls_R_factor_gt                  0.0549
_refine_ls_wR_factor_ref                0.1459
_refine_ls_goodness_of_fit_ref          1.076
_refine_ls_restrained_S_all             1.076
_refine_ls_number_reflns                4065
_refine_ls_number_parameters            321
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           refall
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0555P)²+1.5046P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.443
_refine_diff_density_min                -0.269
_refine_diff_density_rms                0.054
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution           'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
H4 0.975(3) 0.424(2) 0.2979(19) 0.032(6) Uiso d 1 . . H
H6 0.740(4) 0.695(2) 0.275(2) 0.039(7) Uiso d 1 . . H
H7 0.686(4) 0.606(2) 0.351(2) 0.040(7) Uiso d 1 . . H
H1 0.833(3) 0.4235(19) 0.4836(19) 0.029(6) Uiso d 1 . . H
H2A 0.674(4) 0.220(2) 0.288(2) 0.033(6) Uiso d 1 . . H
H2B 0.843(4) 0.150(2) 0.393(2) 0.050(8) Uiso d 1 . . H
H3A 1.064(3) 0.2823(18) 0.4567(19) 0.024(6) Uiso d 1 . . H
H3B 0.941(4) 0.251(2) 0.342(2) 0.044(7) Uiso d 1 . . H
H12 0.694(3) 0.071(2) 0.393(2) 0.034(6) Uiso d 1 . . H
H14 0.661(3) 0.047(2) 0.5826(19) 0.033(6) Uiso d 1 . . H
H16 0.775(3) 0.335(2) 0.5488(18) 0.028(6) Uiso d 1 . . H
H19 0.101(4) 0.394(2) 0.107(2) 0.048(8) Uiso d 1 . . H
H20 0.047(4) 0.503(2) 0.181(2) 0.049(8) Uiso d 1 . . H
H21 0.321(4) 0.560(2) 0.363(2) 0.049(8) Uiso d 1 . . H
H10A 0.829(3) 0.7291(19) 0.1424(19) 0.028(6) Uiso d 1 . . H
H10B 0.869(3) 0.775(2) 0.234(2) 0.030(6) Uiso d 1 . . H
H10C 0.680(4) 0.713(2) 0.134(2) 0.036(7) Uiso d 1 . . H
C9 0.8801(3) 0.40316(16) 0.35165(15) 0.0250(4) Uani d 1 . . C
C4 0.9139(3) 0.45927(17) 0.30745(16) 0.0263(4) Uani d 1 . . C
C5 0.8597(3) 0.56628(16) 0.27693(15) 0.0248(4) Uani d 1 . . C
C6 0.7781(3) 0.61918(17) 0.29495(16) 0.0265(4) Uani d 1 . . C
C7 0.7441(3) 0.56275(17) 0.33879(16) 0.0260(4) Uani d 1 . . C
C8 0.7903(3) 0.45383(16) 0.36537(15) 0.0229(4) Uani d 1 . . C
C1 0.7446(3) 0.39585(16) 0.41058(16) 0.0240(4) Uani d 1 . . C
C2 0.7947(3) 0.22644(17) 0.36379(19) 0.0316(5) Uani d 1 . . C
C3 0.9356(3) 0.28674(17) 0.38295(19) 0.0312(5) Uani d 1 . . C
C11 0.7392(3) 0.21668(16) 0.46096(15) 0.0245(4) Uani d 1 . . C
C12 0.6989(3) 0.10574(17) 0.43809(17) 0.0287(4) Uani d 1 . . C
C13 0.6734(3) 0.04642(17) 0.48454(17) 0.0310(5) Uani d 1 . . C
C14 0.6809(3) 0.08791(18) 0.55119(17) 0.0309(5) Uani d 1 . . C
C15 0.7166(3) 0.19717(18) 0.57030(16) 0.0280(4) Uani d 1 . . C
C16 0.7456(3) 0.26239(17) 0.52814(16) 0.0253(4) Uani d 1 . . C
C17 0.5451(3) 0.42530(16) 0.34577(16) 0.0257(4) Uani d 1 . . C
C18 0.3854(3) 0.39344(18) 0.24041(17) 0.0306(5) Uani d 1 . . C
C19 0.2052(3) 0.4214(2) 0.17995(19) 0.0381(6) Uani d 1 . . C
C20 0.1789(3) 0.4834(2) 0.2248(2) 0.0403(6) Uani d 1 . . C
C21 0.3300(4) 0.5174(2) 0.3282(2) 0.0375(5) Uani d 1 . . C
C22 0.5082(3) 0.48812(17) 0.38510(18) 0.0305(5) Uani d 1 . . C
C10 0.8094(3) 0.71540(18) 0.18142(19) 0.0325(5) Uani d 1 . . C
N1 0.7737(3) 0.27871(13) 0.41969(14) 0.0263(4) Uani d 1 . . N
O1 0.8924(2) 0.61214(12) 0.22969(12) 0.0301(3) Uani d 1 . . O
F1 0.6379(2) -0.06031(11) 0.46189(12) 0.0456(4) Uani d 1 . . F
F2 0.72560(19) 0.24338(10) 0.63547(10) 0.0354(3) Uani d 1 . . F
F3 0.40932(18) 0.33238(12) 0.19587(10) 0.0396(3) Uani d 1 . . F
F4 0.65611(19) 0.52408(11) 0.48627(11) 0.0399(3) Uani d 1 . . F
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C9 C4 . 1.393(3) ?
C9 C8 . 1.393(3) ?
C9 C3 . 1.507(3) ?
C4 H4 . 0.95(2) ?
C4 C5 . 1.392(3) ?
C5 C6 . 1.391(3) ?
C5 O1 . 1.378(2) ?
C6 H6 . 0.99(3) ?
C6 C7 . 1.391(3) ?
C7 H7 . 1.01(3) ?
C7 C8 . 1.400(3) ?
C8 C1 . 1.528(3) ?
C1 H1 . 0.99(2) ?
C1 C17 . 1.539(3) ?
C1 N1 . 1.473(2) ?
C2 H2A . 0.98(3) ?
C2 H2B . 1.03(3) ?
C2 C3 . 1.518(3) ?
C2 N1 . 1.465(3) ?
C3 H3A . 0.98(2) ?
C3 H3B . 0.98(3) ?
C11 C12 . 1.413(3) ?
C11 C16 . 1.408(3) ?
C11 N1 . 1.389(3) ?
C12 H12 . 0.96(3) ?
C12 C13 . 1.381(3) ?
C13 C14 . 1.370(3) ?
C13 F1 . 1.359(2) ?
C14 H14 . 0.96(3) ?
C14 C15 . 1.384(3) ?
C15 C16 . 1.382(3) ?
C15 F2 . 1.355(2) ?
C16 H16 . 0.94(2) ?
C17 C18 . 1.397(3) ?
C17 C22 . 1.384(3) ?
C18 C19 . 1.384(3) ?
C18 F3 . 1.349(3) ?
C19 H19 . 0.99(3) ?
C19 C20 . 1.380(4) ?
C20 H20 . 1.02(3) ?
C20 C21 . 1.374(4) ?
C21 H21 . 0.95(3) ?
C21 C22 . 1.390(3) ?
C22 F4 . 1.356(3) ?
C10 H10A . 0.98(2) ?
C10 H10B . 1.00(2) ?
C10 H10C . 0.94(3) ?
C10 O1 . 1.434(3) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C4 C9 C8 120.04(19) . . ?
C4 C9 C3 120.92(19) . . ?
C8 C9 C3 119.02(18) . . ?
C9 C4 H4 119.6(15) . . ?
C5 C4 H4 119.5(15) . . ?
C5 C4 C9 120.87(19) . . ?
C6 C5 C4 119.57(19) . . ?
O1 C5 C4 115.81(18) . . ?
O1 C5 C6 124.63(18) . . ?
C5 C6 H6 121.3(15) . . ?
C5 C6 C7 119.32(19) . . ?
C7 C6 H6 119.4(15) . . ?
C6 C7 H7 115.7(15) . . ?
C6 C7 C8 121.55(19) . . ?
C8 C7 H7 122.7(15) . . ?
C9 C8 C7 118.53(18) . . ?
C9 C8 C1 122.55(17) . . ?
C7 C8 C1 118.91(17) . . ?
C8 C1 H1 107.0(14) . . ?
C8 C1 C17 109.79(16) . . ?
C17 C1 H1 107.4(14) . . ?
N1 C1 H1 106.7(14) . . ?
N1 C1 C8 113.21(16) . . ?
N1 C1 C17 112.35(16) . . ?
H2A C2 H2B 106(2) . . ?
C3 C2 H2A 111.6(14) . . ?
C3 C2 H2B 108.6(16) . . ?
N1 C2 H2A 111.1(14) . . ?
N1 C2 H2B 108.4(16) . . ?
N1 C2 C3 110.49(18) . . ?
H3A C3 H3B 105(2) . . ?
C9 C3 H3A 109.4(14) . . ?
C9 C3 H3B 111.2(16) . . ?
C9 C3 C2 110.63(19) . . ?
C2 C3 H3A 113.0(13) . . ?
C2 C3 H3B 107.6(16) . . ?
C16 C11 C12 117.90(19) . . ?
N1 C11 C12 121.23(19) . . ?
N1 C11 C16 120.87(18) . . ?
C11 C12 H12 120.5(15) . . ?
C13 C12 H12 120.3(15) . . ?
C13 C12 C11 119.1(2) . . ?
C14 C13 C12 124.5(2) . . ?
F1 C13 C12 117.3(2) . . ?
F1 C13 C14 118.14(19) . . ?
C13 C14 H14 124.6(15) . . ?
C13 C14 C15 115.0(2) . . ?
C15 C14 H14 120.4(15) . . ?
C16 C15 C14 124.4(2) . . ?
F2 C15 C14 118.03(19) . . ?
F2 C15 C16 117.59(19) . . ?
C11 C16 H16 123.0(14) . . ?
C15 C16 H16 117.9(14) . . ?
C15 C16 C11 119.04(19) . . ?
C18 C17 C1 122.53(19) . . ?
C22 C17 C1 123.26(19) . . ?
C22 C17 C18 114.18(19) . . ?
C19 C18 C17 123.4(2) . . ?
F3 C18 C17 117.91(19) . . ?
F3 C18 C19 118.7(2) . . ?
C18 C19 H19 117.8(16) . . ?
C20 C19 H19 123.0(16) . . ?
C20 C19 C18 119.2(2) . . ?
C19 C20 H20 119.7(16) . . ?
C21 C20 H20 119.9(16) . . ?
C21 C20 C19 120.4(2) . . ?
C20 C21 H21 124.2(18) . . ?
C20 C21 C22 118.2(2) . . ?
C22 C21 H21 117.6(18) . . ?
C17 C22 C21 124.7(2) . . ?
F4 C22 C17 117.85(19) . . ?
F4 C22 C21 117.5(2) . . ?
H10A C10 H10B 108.3(19) . . ?
H10A C10 H10C 110(2) . . ?
H10B C10 H10C 110(2) . . ?
O1 C10 H10A 104.8(14) . . ?
O1 C10 H10B 113.6(14) . . ?
O1 C10 H10C 110.3(16) . . ?
C2 N1 C1 119.84(16) . . ?
C11 N1 C1 118.93(17) . . ?
C11 N1 C2 119.68(16) . . ?
C5 O1 C10 116.63(17) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C9 C4 C5 C6 2.8(3) . . . . ?
C9 C4 C5 O1 -177.11(18) . . . . ?
C9 C8 C1 C17 -136.73(19) . . . . ?
C9 C8 C1 N1 -10.3(3) . . . . ?
C4 C9 C8 C7 -3.1(3) . . . . ?
C4 C9 C8 C1 178.31(18) . . . . ?
C4 C9 C3 C2 -145.1(2) . . . . ?
C4 C5 C6 C7 -2.9(3) . . . . ?
C4 C5 O1 C10 169.60(18) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C5 O1 C10 -10.3(3) . . . . ?
C6 C7 C8 C9 3.0(3) . . . . ?
C6 C7 C8 C1 -178.43(18) . . . . ?
C7 C8 C1 C17 44.7(2) . . . . ?
C7 C8 C1 N1 171.18(17) . . . . ?
C8 C9 C4 C5 0.3(3) . . . . ?
C8 C9 C3 C2 33.5(3) . . . . ?
C8 C1 C17 C18 67.4(2) . . . . ?
C8 C1 C17 C22 -110.5(2) . . . . ?
C8 C1 N1 C2 -15.0(3) . . . . ?
C8 C1 N1 C11 179.24(17) . . . . ?
C1 C17 C18 C19 -178.27(19) . . . . ?
C1 C17 C18 F3 1.6(3) . . . . ?
C1 C17 C22 C21 179.1(2) . . . . ?
C1 C17 C22 F4 -0.8(3) . . . . ?
C3 C9 C4 C5 178.9(2) . . . . ?
C3 C9 C8 C7 178.25(19) . . . . ?
C3 C9 C8 C1 -0.3(3) . . . . ?
C3 C2 N1 C1 48.2(3) . . . . ?
C3 C2 N1 C11 -146.16(19) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C11 C12 C13 F1 -178.97(19) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
C12 C11 N1 C1 157.14(19) . . . . ?
C12 C11 N1 C2 -8.6(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C13 C14 C15 F2 179.92(18) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C16 C11 C12 C13 -1.9(3) . . . . ?
C16 C11 N1 C1 -23.7(3) . . . . ?
C16 C11 N1 C2 170.58(19) . . . . ?
C17 C1 N1 C2 110.1(2) . . . . ?
C17 C1 N1 C11 -55.7(2) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C18 C17 C22 F4 -178.79(18) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C17 -1.2(3) . . . . ?
C20 C21 C22 F4 178.67(19) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C22 C17 C18 F3 179.68(18) . . . . ?
N1 C1 C17 C18 -59.6(2) . . . . ?
N1 C1 C17 C22 122.6(2) . . . . ?
N1 C2 C3 C9 -55.7(2) . . . . ?
N1 C11 C12 C13 177.27(19) . . . . ?
N1 C11 C16 C15 -177.87(18) . . . . ?
O1 C5 C6 C7 176.93(18) . . . . ?
F1 C13 C14 C15 -179.68(19) . . . . ?
F2 C15 C16 C11 179.35(18) . . . . ?
F3 C18 C19 C20 179.66(19) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

 
data_6-37
_database_code_depnum_ccdc_archive 'CCDC 1540730'
 
_audit_creation_date                    2020-03-09T09:20:26-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#==============================================================================
 
# CHEMICAL DATA
 
_chemical_formula_moiety                'C22 H21 N O'
_chemical_formula_sum                   'C22 H21 N O'
_chemical_formula_weight                315.4
 
#==============================================================================
 
# CRYSTAL DATA
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P b c a'
_symmetry_space_group_name_Hall         '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'
 '-x, -y, -z'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 'x-1/2, y, -z-1/2'

_cell_length_a                          10.3744(14)
_cell_length_b                          16.379(2)
_cell_length_c                          19.851(3)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            3373.2(8)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           4212
_cell_measurement_theta_min             2.49
_cell_measurement_theta_max             25.04
_cell_measurement_temperature           100
_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.2
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.1
_exptl_crystal_density_diffrn           1.242
_exptl_crystal_F_000                    1344
_exptl_absorpt_coefficient_mu           0.075
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
        wR2(int) was 0.0586 before and 0.0507 after correction.
        The Ratio of minimum to maximum transmission is 0.8737.
        The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min         0.6511
_exptl_absorpt_correction_T_max         0.7452
 
#==============================================================================
 
# EXPERIMENTAL DATA
 
_diffrn_ambient_temperature             100
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_measurement_device_type         'Bruker APEX-II CCD'
_diffrn_measurement_method              'φ and ω scans'
_diffrn_reflns_number                   16968
_diffrn_reflns_av_R_equivalents         0.0415
_diffrn_reflns_theta_min                2.052
_diffrn_reflns_theta_max                25.178
_diffrn_reflns_theta_full               25.178
_diffrn_measured_fraction_theta_max
                                        0.993
_diffrn_measured_fraction_theta_full
                                        0.993
_diffrn_reflns_Laue_measured_fraction_full
                                        0.993
_diffrn_reflns_Laue_measured_fraction_max
                                        0.993
_diffrn_reflns_point_group_measured_fraction_full
                                        0.993
_diffrn_reflns_point_group_measured_fraction_max
                                        0.993
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -19
_diffrn_reflns_limit_k_max              19
_diffrn_reflns_limit_l_min              -23
_diffrn_reflns_limit_l_max              23
 
#==============================================================================
 
# STRUCTURE SOLUTION
 
_atom_sites_solution_hydrogens          geom
 
#==============================================================================
 
# REFINEMENT DATA
 
_reflns_number_total                    3014
_reflns_number_gt                       2421
_reflns_threshold_expression            'I > 2σ(I)'
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0497
_refine_ls_R_factor_gt                  0.0359
_refine_ls_wR_factor_ref                0.0891
_refine_ls_goodness_of_fit_ref          1.017
_refine_ls_restrained_S_all             1.017
_refine_ls_number_reflns                3014
_refine_ls_number_parameters            218
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0401P)²+0.9976P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.182
_refine_diff_density_min                -0.19
_refine_diff_density_rms                0.038
_refine_ls_extinction_method            none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_computing_cell_refinement              'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction               'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution           'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement         'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics           'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material         'Olex2 (Dolomanov et al., 2009)'
 
#==============================================================================
 
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
C9 0.45217(13) 1.04334(8) 0.60640(7) 0.0180(3) Uani d 1 . . C
C4 0.54887(13) 1.09986(8) 0.61773(7) 0.0199(3) Uani d 1 . . C
H4 0.5639 1.142 0.5858 0.024 Uiso calc 1 . . H
C5 0.62455(12) 1.09529(8) 0.67590(7) 0.0189(3) Uani d 1 . . C
C6 0.60074(13) 1.03560(8) 0.72360(7) 0.0194(3) Uani d 1 . . C
H6 0.6509 1.0329 0.7636 0.023 Uiso calc 1 . . H
C7 0.50221(12) 0.97966(8) 0.71219(7) 0.0184(3) Uani d 1 . . C
H7 0.4849 0.9389 0.745 0.022 Uiso calc 1 . . H
C8 0.42866(12) 0.98214(8) 0.65379(7) 0.0166(3) Uani d 1 . . C
C1 0.32357(12) 0.91998(8) 0.64046(7) 0.0169(3) Uani d 1 . . C
H1 0.2953 0.8987 0.6853 0.02 Uiso calc 1 . . H
C2 0.22484(13) 1.03447(9) 0.57094(7) 0.0213(3) Uani d 1 . . C
H2A 0.1997 1.0814 0.5995 0.026 Uiso calc 1 . . H
H2B 0.1663 1.033 0.5316 0.026 Uiso calc 1 . . H
C3 0.36254(13) 1.04616(9) 0.54678(7) 0.0219(3) Uani d 1 . . C
H3A 0.3854 1.0025 0.5144 0.026 Uiso calc 1 . . H
H3B 0.3708 1.0994 0.5236 0.026 Uiso calc 1 . . H
C11 0.08884(13) 0.92805(9) 0.62232(7) 0.0194(3) Uani d 1 . . C
C12 -0.02221(14) 0.97376(10) 0.60749(7) 0.0250(3) Uani d 1 . . C
H12 -0.0142 1.0265 0.5881 0.03 Uiso calc 1 . . H
C13 -0.14390(14) 0.94204(10) 0.62117(8) 0.0305(4) Uani d 1 . . C
H13 -0.2182 0.9735 0.6108 0.037 Uiso calc 1 . . H
C14 -0.15869(14) 0.86553(10) 0.64965(8) 0.0314(4) Uani d 1 . . C
H14 -0.2421 0.8447 0.6594 0.038 Uiso calc 1 . . H
C15 -0.04989(14) 0.81987(10) 0.66374(8) 0.0279(4) Uani d 1 . . C
H15 -0.0589 0.7671 0.683 0.033 Uiso calc 1 . . H
C16 0.07184(13) 0.84996(9) 0.65020(7) 0.0221(3) Uani d 1 . . C
H16 0.1452 0.8173 0.6599 0.026 Uiso calc 1 . . H
C17 0.37273(12) 0.84634(8) 0.59993(7) 0.0176(3) Uani d 1 . . C
C18 0.47875(13) 0.80251(9) 0.62271(8) 0.0244(3) Uani d 1 . . C
H18 0.5214 0.8192 0.6628 0.029 Uiso calc 1 . . H
C19 0.52333(14) 0.73472(9) 0.58778(8) 0.0292(4) Uani d 1 . . C
H19 0.5968 0.706 0.6036 0.035 Uiso calc 1 . . H
C20 0.46097(14) 0.70897(9) 0.52998(8) 0.0258(3) Uani d 1 . . C
H20 0.4915 0.6627 0.5059 0.031 Uiso calc 1 . . H
C21 0.35400(14) 0.75112(9) 0.50756(7) 0.0237(3) Uani d 1 . . C
H21 0.3097 0.7332 0.4684 0.028 Uiso calc 1 . . H
C22 0.31102(13) 0.81953(9) 0.54197(7) 0.0210(3) Uani d 1 . . C
H22 0.2382 0.8485 0.5256 0.025 Uiso calc 1 . . H
C10 0.78759(15) 1.15802(10) 0.74362(8) 0.0333(4) Uani d 1 . . C
H10A 0.7259 1.1668 0.7803 0.05 Uiso calc 1 . . H
H10B 0.8486 1.2036 0.7421 0.05 Uiso calc 1 . . H
H10C 0.8346 1.107 0.7514 0.05 Uiso calc 1 . . H
N1 0.21069(10) 0.95880(7) 0.60956(6) 0.0191(3) Uani d 1 . . N
O1 0.71989(9) 1.15307(6) 0.68098(5) 0.0248(3) Uani d 1 . . O
 
 
 
#==============================================================================
 
# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
C9 C4 . 1.3835(19) ?
C9 C8 . 1.3962(19) ?
C9 C3 . 1.5058(19) ?
C4 H4 . 0.95 ?
C4 C5 . 1.3983(19) ?
C5 C6 . 1.3833(19) ?
C5 O1 . 1.3726(16) ?
C6 H6 . 0.95 ?
C6 C7 . 1.3913(19) ?
C7 H7 . 0.95 ?
C7 C8 . 1.3885(19) ?
C8 C1 . 1.5151(18) ?
C1 H1 . 1 ?
C1 C17 . 1.5369(19) ?
C1 N1 . 1.4670(16) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.5190(19) ?
C2 N1 . 1.4646(18) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C12 . 1.405(2) ?
C11 C16 . 1.405(2) ?
C11 N1 . 1.3841(17) ?
C12 H12 . 0.95 ?
C12 C13 . 1.392(2) ?
C13 H13 . 0.95 ?
C13 C14 . 1.383(2) ?
C14 H14 . 0.95 ?
C14 C15 . 1.383(2) ?
C15 H15 . 0.95 ?
C15 C16 . 1.382(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3891(19) ?
C17 C22 . 1.388(2) ?
C18 H18 . 0.95 ?
C18 C19 . 1.388(2) ?
C19 H19 . 0.95 ?
C19 C20 . 1.383(2) ?
C20 H20 . 0.95 ?
C20 C21 . 1.381(2) ?
C21 H21 . 0.95 ?
C21 C22 . 1.386(2) ?
C22 H22 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.4304(17) ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C4 C9 C8 119.83(13) . . ?
C4 C9 C3 123.72(12) . . ?
C8 C9 C3 116.34(12) . . ?
C9 C4 H4 119.8 . . ?
C9 C4 C5 120.37(13) . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.19(13) . . ?
O1 C5 C4 115.36(12) . . ?
O1 C5 C6 124.45(12) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.02(13) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.36(13) . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C1 119.37(12) . . ?
C7 C8 C9 119.18(13) . . ?
C7 C8 C1 121.44(12) . . ?
C8 C1 H1 106.8 . . ?
C8 C1 C17 112.33(10) . . ?
C17 C1 H1 106.8 . . ?
N1 C1 C8 110.86(11) . . ?
N1 C1 H1 106.8 . . ?
N1 C1 C17 112.72(11) . . ?
H2A C2 H2B 108 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
N1 C2 C3 111.49(11) . . ?
C9 C3 C2 109.19(11) . . ?
C9 C3 H3A 109.8 . . ?
C9 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C16 C11 C12 117.69(13) . . ?
N1 C11 C12 121.10(13) . . ?
N1 C11 C16 121.21(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.26(15) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.23(14) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.83(14) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.91(15) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.07(14) . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C1 119.87(12) . . ?
C22 C17 C1 121.94(12) . . ?
C22 C17 C18 118.13(13) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.97(14) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.16(14) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.39(14) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.27(14) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.06(13) . . ?
C21 C22 H22 119.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C2 N1 C1 120.37(11) . . ?
C11 N1 C1 119.65(11) . . ?
C11 N1 C2 119.69(11) . . ?
C5 O1 C10 117.18(11) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C9 C4 C5 C6 -2.0(2) . . . . ?
C9 C4 C5 O1 178.22(12) . . . . ?
C9 C8 C1 C17 87.61(15) . . . . ?
C9 C8 C1 N1 -39.51(16) . . . . ?
C4 C9 C8 C7 0.76(19) . . . . ?
C4 C9 C8 C1 -179.28(12) . . . . ?
C4 C9 C3 C2 -132.67(14) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C4 C5 O1 C10 171.41(12) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C5 O1 C10 -8.40(19) . . . . ?
C6 C7 C8 C9 -1.6(2) . . . . ?
C6 C7 C8 C1 178.43(12) . . . . ?
C7 C8 C1 C17 -92.43(15) . . . . ?
C7 C8 C1 N1 140.44(13) . . . . ?
C8 C9 C4 C5 1.0(2) . . . . ?
C8 C9 C3 C2 43.55(16) . . . . ?
C8 C1 C17 C18 54.26(16) . . . . ?
C8 C1 C17 C22 -128.47(13) . . . . ?
C8 C1 N1 C2 25.20(16) . . . . ?
C8 C1 N1 C11 -148.67(12) . . . . ?
C1 C17 C18 C19 178.61(13) . . . . ?
C1 C17 C22 C21 -177.52(12) . . . . ?
C3 C9 C4 C5 177.10(13) . . . . ?
C3 C9 C8 C7 -175.62(12) . . . . ?
C3 C9 C8 C1 4.34(18) . . . . ?
C3 C2 N1 C1 21.05(17) . . . . ?
C3 C2 N1 C11 -165.08(12) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C12 C11 N1 C1 164.63(12) . . . . ?
C12 C11 N1 C2 -9.28(19) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C16 C11 N1 C1 -15.70(19) . . . . ?
C16 C11 N1 C2 170.40(12) . . . . ?
C17 C1 N1 C2 -101.71(14) . . . . ?
C17 C1 N1 C11 84.42(14) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C18 C17 C22 C21 -0.2(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C22 1.2(2) . . . . ?
C20 C21 C22 C17 -1.0(2) . . . . ?
C22 C17 C18 C19 1.2(2) . . . . ?
N1 C1 C17 C18 -179.62(12) . . . . ?
N1 C1 C17 C22 -2.34(18) . . . . ?
N1 C2 C3 C9 -55.66(15) . . . . ?
N1 C11 C12 C13 -179.49(13) . . . . ?
N1 C11 C16 C15 179.10(13) . . . . ?
O1 C5 C6 C7 -179.09(12) . . . . ?
 
 
 
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
 
# END of CIF

