##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2009-05-21
_journal_date_accepted     2009-06-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     o1530
_journal_page_last     o1530
_journal_paper_category     QO
_journal_coeditor_code     CI2811
_publ_contact_author_name     'Dr Professor P.L. Nilantha Lakshman'
_publ_contact_author_address
;
Department of  Food science and Technology
Faculty of Agriculture
University of Ruhuna
Mapalana
Kamburupitiya (81100)
Sri Lanka.
;
_publ_contact_author_email     nilanthalakshman@yahoo.co.uk
_publ_contact_author_fax     '+94-41-2292384'
_publ_contact_author_phone     '+94-41-2292200'
_publ_section_title
;
4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'S. Natarajan' .
;
Department of Physics
Madurai Kamaraj University
Madurai 625 021
India
;
    'V. Sudha Priya' .
;
Organic Chemistry Division
School of Science and Humanities
VIT University
Vellore 632 014
India
;
    'V. Vijayakumar' .
;
Organic Chemistry Division
School of Science and Humanities
VIT University
Vellore 632 014
India
;
    'J. Suresh' .
;
Department of Physics
The Madura College
Madurai 625 011
India
;
    'P. L. Nilantha Lakshman' .
;
Department of Food Science and Technology
Faculty of Agriculture
University of Ruhuna
Mapalana
Kamburupitiya 81100
Sri Lanka
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H24 F4 N2 O'
_chemical_formula_sum     'C32 H24 F4 N2 O'
_chemical_formula_iupac     'C32 H24 F4 N2 O'
_chemical_formula_weight     528.53
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.8432(7)
_cell_length_b     12.5045(11)
_cell_length_c     28.8930(15)
_cell_angle_alpha     90.00
_cell_angle_beta     92.393(12)
_cell_angle_gamma     90.00
_cell_volume     2470.2(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     2
_cell_measurement_theta_max     25
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.421
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1096
_exptl_absorpt_coefficient_mu     0.107
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9810
_exptl_absorpt_correction_T_max     0.9883
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius MACH-3'
_diffrn_measurement_method     ω-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5226
_diffrn_reflns_av_R_equivalents     0.0299
_diffrn_reflns_av_sigmaI/netI     0.0422
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     24.94
_diffrn_reflns_theta_full     24.94
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -34
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4311
_reflns_number_gt     2643
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0892
_refine_ls_R_factor_gt     0.0376
_refine_ls_wR_factor_gt     0.0835
_refine_ls_wR_factor_ref     0.1050
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     4311
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0383P)²+0.9132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.152
_refine_diff_density_min     -0.187
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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' 0.0000 0.0000
                         '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 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 0.4689(2) 0.36204(14) 0.13950(4) 0.0733(5) Uani d . 1 . .
    N N2 0.1830(2) 0.24192(14) 0.41569(6) 0.0358(4) Uani d . 1 . .
    O O1 0.6262(2) 0.13710(13) 0.34356(5) 0.0509(4) Uani d . 1 . .
    N N1 0.0911(2) 0.27089(13) 0.33278(5) 0.0338(4) Uani d . 1 . .
    C C31 0.0364(3) 0.28261(18) 0.38120(7) 0.0356(5) Uani d . 1 . .
    H H31A -0.0859 0.2451 0.3852 0.043 Uiso calc R 1 . .
    H H31B 0.0138 0.3578 0.3873 0.043 Uiso calc R 1 . .
    C C13 0.1194(3) 0.12606(16) 0.27355(7) 0.0354(5) Uani d . 1 . .
    C C25 0.2719(3) 0.33390(17) 0.32685(7) 0.0364(5) Uani d . 1 . .
    H H25 0.2421 0.4070 0.3366 0.044 Uiso calc R 1 . .
    C C19 0.0608(3) 0.05446(18) 0.42272(7) 0.0383(5) Uani d . 1 . .
    C C7 0.3307(3) 0.34202(17) 0.27660(7) 0.0368(5) Uani d . 1 . .
    F F2 0.1029(3) 0.06663(15) 0.13313(5) 0.0867(5) Uani d . 1 . .
    C C26 0.4369(3) 0.29316(18) 0.36103(7) 0.0370(5) Uani d . 1 . .
    H H26 0.5580 0.3336 0.3573 0.044 Uiso calc R 1 . .
    C C30 0.1145(3) 0.15392(16) 0.32469(7) 0.0341(5) Uani d . 1 . .
    H H30 -0.0045 0.1206 0.3357 0.041 Uiso calc R 1 . .
    C C28 0.2248(3) 0.12796(17) 0.40808(7) 0.0370(5) Uani d . 1 . .
    H H28 0.3401 0.1104 0.4279 0.044 Uiso calc R 1 . .
    C C16 0.1080(4) 0.0848(2) 0.17976(8) 0.0538(6) Uani d . 1 . .
    F F3 0.3014(3) 0.71627(13) 0.48734(7) 0.0909(6) Uani d . 1 . .
    C C27 0.3665(3) 0.30274(18) 0.41170(7) 0.0382(5) Uani d . 1 . .
    H H27 0.4653 0.2671 0.4318 0.046 Uiso calc R 1 . .
    F F4 -0.3548(3) -0.15156(15) 0.47007(6) 0.0952(6) Uani d . 1 . .
    C C29 0.2842(3) 0.11061(17) 0.35659(7) 0.0352(5) Uani d . 1 . .
    H H29 0.3084 0.0348 0.3504 0.042 Uiso calc R 1 . .
    C C32 0.4680(3) 0.17575(18) 0.35196(7) 0.0370(5) Uani d . 1 . .
    C C1 0.3471(3) 0.41640(19) 0.42984(7) 0.0418(5) Uani d . 1 . .
    C C14 0.2848(3) 0.09058(18) 0.25191(7) 0.0443(6) Uani d . 1 . .
    H H14 0.4006 0.0799 0.2693 0.053 Uiso calc R 1 . .
    C C2 0.4283(4) 0.5051(2) 0.40927(8) 0.0587(7) Uani d . 1 . .
    H H2 0.4948 0.4964 0.3821 0.070 Uiso calc R 1 . .
    C C9 0.5671(4) 0.3332(2) 0.21705(8) 0.0495(6) Uani d . 1 . .
    H H9 0.6946 0.3219 0.2082 0.059 Uiso calc R 1 . .
    C C12 0.1894(3) 0.37033(18) 0.24280(7) 0.0450(6) Uani d . 1 . .
    H H12 0.0622 0.3841 0.2513 0.054 Uiso calc R 1 . .
    C C10 0.4229(4) 0.35754(19) 0.18512(7) 0.0495(6) Uani d . 1 . .
    C C11 0.2350(4) 0.3783(2) 0.19679(8) 0.0526(6) Uani d . 1 . .
    H H11 0.1402 0.3973 0.1743 0.063 Uiso calc R 1 . .
    C C8 0.5205(3) 0.32557(18) 0.26322(7) 0.0439(6) Uani d . 1 . .
    H H8 0.6180 0.3092 0.2855 0.053 Uiso calc R 1 . .
    C C18 -0.0533(3) 0.13593(18) 0.24691(7) 0.0434(5) Uani d . 1 . .
    H H18 -0.1670 0.1561 0.2611 0.052 Uiso calc R 1 . .
    C C24 0.0710(4) -0.0547(2) 0.41421(8) 0.0505(6) Uani d . 1 . .
    H H24 0.1739 -0.0815 0.3977 0.061 Uiso calc R 1 . .
    C C20 -0.0907(3) 0.0918(2) 0.44877(7) 0.0464(6) Uani d . 1 . .
    H H20 -0.0974 0.1642 0.4558 0.056 Uiso calc R 1 . .
    C C17 -0.0600(4) 0.1166(2) 0.19989(8) 0.0514(6) Uani d . 1 . .
    H H17 -0.1759 0.1249 0.1823 0.062 Uiso calc R 1 . .
    C C6 0.2532(3) 0.4316(2) 0.47098(8) 0.0523(6) Uani d . 1 . .
    H H6 0.1993 0.3732 0.4858 0.063 Uiso calc R 1 . .
    C C23 -0.0689(4) -0.1245(2) 0.42991(9) 0.0625(7) Uani d . 1 . .
    H H23 -0.0620 -0.1975 0.4239 0.075 Uiso calc R 1 . .
    C C15 0.2792(4) 0.0710(2) 0.20472(8) 0.0546(7) Uani d . 1 . .
    H H15 0.3910 0.0487 0.1902 0.066 Uiso calc R 1 . .
    C C4 0.3170(4) 0.6172(2) 0.46791(10) 0.0617(7) Uani d . 1 . .
    C C21 -0.2320(4) 0.0232(2) 0.46442(8) 0.0560(7) Uani d . 1 . .
    H H21 -0.3347 0.0488 0.4814 0.067 Uiso calc R 1 . .
    C C22 -0.2172(4) -0.0828(3) 0.45442(8) 0.0616(8) Uani d . 1 . .
    C C5 0.2387(4) 0.5326(2) 0.49038(10) 0.0615(8) Uani d . 1 . .
    H H5 0.1768 0.5423 0.5181 0.074 Uiso calc R 1 . .
    C C3 0.4128(4) 0.6063(2) 0.42818(10) 0.0685(8) Uani d . 1 . .
    H H3 0.4669 0.6654 0.4139 0.082 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C10 . 1.369(2) ?
    N2 C28 . 1.472(3) ?
    N2 C31 . 1.475(3) ?
    N2 C27 . 1.477(3) ?
    O1 C32 . 1.219(2) ?
    N1 C31 . 1.471(2) ?
    N1 C25 . 1.483(3) ?
    N1 C30 . 1.491(3) ?
    C31 H31A . 0.97 ?
    C31 H31B . 0.97 ?
    C13 C18 . 1.388(3) ?
    C13 C14 . 1.389(3) ?
    C13 C30 . 1.520(3) ?
    C25 C7 . 1.526(3) ?
    C25 C26 . 1.555(3) ?
    C25 H25 . 0.98 ?
    C19 C20 . 1.387(3) ?
    C19 C24 . 1.390(3) ?
    C19 C28 . 1.524(3) ?
    C7 C8 . 1.386(3) ?
    C7 C12 . 1.391(3) ?
    F2 C16 . 1.365(3) ?
    C26 C32 . 1.508(3) ?
    C26 C27 . 1.565(3) ?
    C26 H26 . 0.98 ?
    C30 C29 . 1.550(3) ?
    C30 H30 . 0.98 ?
    C28 C29 . 1.574(3) ?
    C28 H28 . 0.98 ?
    C16 C15 . 1.361(3) ?
    C16 C17 . 1.369(3) ?
    F3 C4 . 1.366(3) ?
    C27 C1 . 1.523(3) ?
    C27 H27 . 0.98 ?
    F4 C22 . 1.366(3) ?
    C29 C32 . 1.509(3) ?
    C29 H29 . 0.98 ?
    C1 C2 . 1.386(3) ?
    C1 C6 . 1.387(3) ?
    C14 C15 . 1.384(3) ?
    C14 H14 . 0.93 ?
    C2 C3 . 1.384(4) ?
    C2 H2 . 0.93 ?
    C9 C10 . 1.357(3) ?
    C9 C8 . 1.388(3) ?
    C9 H9 . 0.93 ?
    C12 C11 . 1.381(3) ?
    C12 H12 . 0.93 ?
    C10 C11 . 1.368(3) ?
    C11 H11 . 0.93 ?
    C8 H8 . 0.93 ?
    C18 C17 . 1.379(3) ?
    C18 H18 . 0.93 ?
    C24 C23 . 1.386(3) ?
    C24 H24 . 0.93 ?
    C20 C21 . 1.383(3) ?
    C20 H20 . 0.93 ?
    C17 H17 . 0.93 ?
    C6 C5 . 1.387(4) ?
    C6 H6 . 0.93 ?
    C23 C22 . 1.365(4) ?
    C23 H23 . 0.93 ?
    C15 H15 . 0.93 ?
    C4 C3 . 1.352(4) ?
    C4 C5 . 1.363(4) ?
    C21 C22 . 1.361(4) ?
    C21 H21 . 0.93 ?
    C5 H5 . 0.93 ?
    C3 H3 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C28 N2 C31 . . 111.35(16) ?
    C28 N2 C27 . . 108.43(16) ?
    C31 N2 C27 . . 109.05(16) ?
    C31 N1 C25 . . 107.70(15) ?
    C31 N1 C30 . . 106.28(16) ?
    C25 N1 C30 . . 114.06(16) ?
    N1 C31 N2 . . 114.51(16) ?
    N1 C31 H31A . . 108.6 ?
    N2 C31 H31A . . 108.6 ?
    N1 C31 H31B . . 108.6 ?
    N2 C31 H31B . . 108.6 ?
    H31A C31 H31B . . 107.6 ?
    C18 C13 C14 . . 118.0(2) ?
    C18 C13 C30 . . 117.77(18) ?
    C14 C13 C30 . . 124.22(19) ?
    N1 C25 C7 . . 113.58(16) ?
    N1 C25 C26 . . 109.86(16) ?
    C7 C25 C26 . . 114.37(17) ?
    N1 C25 H25 . . 106.1 ?
    C7 C25 H25 . . 106.1 ?
    C26 C25 H25 . . 106.1 ?
    C20 C19 C24 . . 118.1(2) ?
    C20 C19 C28 . . 121.6(2) ?
    C24 C19 C28 . . 120.0(2) ?
    C8 C7 C12 . . 118.30(19) ?
    C8 C7 C25 . . 122.90(19) ?
    C12 C7 C25 . . 118.78(19) ?
    C32 C26 C25 . . 108.21(17) ?
    C32 C26 C27 . . 106.77(17) ?
    C25 C26 C27 . . 108.98(17) ?
    C32 C26 H26 . . 110.9 ?
    C25 C26 H26 . . 110.9 ?
    C27 C26 H26 . . 110.9 ?
    N1 C30 C13 . . 112.60(16) ?
    N1 C30 C29 . . 109.41(16) ?
    C13 C30 C29 . . 116.86(17) ?
    N1 C30 H30 . . 105.7 ?
    C13 C30 H30 . . 105.7 ?
    C29 C30 H30 . . 105.7 ?
    N2 C28 C19 . . 113.13(17) ?
    N2 C28 C29 . . 109.52(16) ?
    C19 C28 C29 . . 113.68(17) ?
    N2 C28 H28 . . 106.7 ?
    C19 C28 H28 . . 106.7 ?
    C29 C28 H28 . . 106.7 ?
    C15 C16 F2 . . 119.2(2) ?
    C15 C16 C17 . . 122.1(2) ?
    F2 C16 C17 . . 118.7(2) ?
    N2 C27 C1 . . 111.55(17) ?
    N2 C27 C26 . . 109.24(16) ?
    C1 C27 C26 . . 115.36(18) ?
    N2 C27 H27 . . 106.7 ?
    C1 C27 H27 . . 106.7 ?
    C26 C27 H27 . . 106.7 ?
    C32 C29 C30 . . 111.42(17) ?
    C32 C29 C28 . . 105.00(16) ?
    C30 C29 C28 . . 107.29(16) ?
    C32 C29 H29 . . 111.0 ?
    C30 C29 H29 . . 111.0 ?
    C28 C29 H29 . . 111.0 ?
    O1 C32 C26 . . 123.6(2) ?
    O1 C32 C29 . . 123.6(2) ?
    C26 C32 C29 . . 112.70(18) ?
    C2 C1 C6 . . 117.8(2) ?
    C2 C1 C27 . . 123.86(19) ?
    C6 C1 C27 . . 118.2(2) ?
    C15 C14 C13 . . 120.7(2) ?
    C15 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.7 ?
    C3 C2 C1 . . 121.6(2) ?
    C3 C2 H2 . . 119.2 ?
    C1 C2 H2 . . 119.2 ?
    C10 C9 C8 . . 118.6(2) ?
    C10 C9 H9 . . 120.7 ?
    C8 C9 H9 . . 120.7 ?
    C11 C12 C7 . . 121.0(2) ?
    C11 C12 H12 . . 119.5 ?
    C7 C12 H12 . . 119.5 ?
    C9 C10 C11 . . 122.7(2) ?
    C9 C10 F1 . . 118.3(2) ?
    C11 C10 F1 . . 119.0(2) ?
    C10 C11 C12 . . 118.4(2) ?
    C10 C11 H11 . . 120.8 ?
    C12 C11 H11 . . 120.8 ?
    C7 C8 C9 . . 120.9(2) ?
    C7 C8 H8 . . 119.5 ?
    C9 C8 H8 . . 119.5 ?
    C17 C18 C13 . . 121.6(2) ?
    C17 C18 H18 . . 119.2 ?
    C13 C18 H18 . . 119.2 ?
    C23 C24 C19 . . 121.3(2) ?
    C23 C24 H24 . . 119.3 ?
    C19 C24 H24 . . 119.3 ?
    C21 C20 C19 . . 121.2(2) ?
    C21 C20 H20 . . 119.4 ?
    C19 C20 H20 . . 119.4 ?
    C16 C17 C18 . . 118.4(2) ?
    C16 C17 H17 . . 120.8 ?
    C18 C17 H17 . . 120.8 ?
    C5 C6 C1 . . 120.9(3) ?
    C5 C6 H6 . . 119.5 ?
    C1 C6 H6 . . 119.5 ?
    C22 C23 C24 . . 117.9(3) ?
    C22 C23 H23 . . 121.0 ?
    C24 C23 H23 . . 121.0 ?
    C16 C15 C14 . . 119.2(2) ?
    C16 C15 H15 . . 120.4 ?
    C14 C15 H15 . . 120.4 ?
    C3 C4 C5 . . 122.7(3) ?
    C3 C4 F3 . . 119.3(3) ?
    C5 C4 F3 . . 118.0(3) ?
    C22 C21 C20 . . 118.4(2) ?
    C22 C21 H21 . . 120.8 ?
    C20 C21 H21 . . 120.8 ?
    C21 C22 C23 . . 123.1(2) ?
    C21 C22 F4 . . 118.9(3) ?
    C23 C22 F4 . . 118.0(3) ?
    C4 C5 C6 . . 118.6(2) ?
    C4 C5 H5 . . 120.7 ?
    C6 C5 H5 . . 120.7 ?
    C4 C3 C2 . . 118.3(3) ?
    C4 C3 H3 . . 120.8 ?
    C2 C3 H3 . . 120.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C25 N1 C31 N2 . . . . -61.6(2) ?
    C30 N1 C31 N2 . . . . 61.0(2) ?
    C28 N2 C31 N1 . . . . -58.1(2) ?
    C27 N2 C31 N1 . . . . 61.6(2) ?
    C31 N1 C25 C7 . . . . -171.95(17) ?
    C30 N1 C25 C7 . . . . 70.4(2) ?
    C31 N1 C25 C26 . . . . 58.5(2) ?
    C30 N1 C25 C26 . . . . -59.2(2) ?
    N1 C25 C7 C8 . . . . -133.8(2) ?
    C26 C25 C7 C8 . . . . -6.6(3) ?
    N1 C25 C7 C12 . . . . 48.2(3) ?
    C26 C25 C7 C12 . . . . 175.45(19) ?
    N1 C25 C26 C32 . . . . 57.6(2) ?
    C7 C25 C26 C32 . . . . -71.5(2) ?
    N1 C25 C26 C27 . . . . -58.2(2) ?
    C7 C25 C26 C27 . . . . 172.74(18) ?
    C31 N1 C30 C13 . . . . 165.18(15) ?
    C25 N1 C30 C13 . . . . -76.3(2) ?
    C31 N1 C30 C29 . . . . -63.10(19) ?
    C25 N1 C30 C29 . . . . 55.4(2) ?
    C18 C13 C30 N1 . . . . -70.4(2) ?
    C14 C13 C30 N1 . . . . 110.1(2) ?
    C18 C13 C30 C29 . . . . 161.69(19) ?
    C14 C13 C30 C29 . . . . -17.8(3) ?
    C31 N2 C28 C19 . . . . -74.0(2) ?
    C27 N2 C28 C19 . . . . 165.99(16) ?
    C31 N2 C28 C29 . . . . 53.9(2) ?
    C27 N2 C28 C29 . . . . -66.1(2) ?
    C20 C19 C28 N2 . . . . -12.0(3) ?
    C24 C19 C28 N2 . . . . 174.70(19) ?
    C20 C19 C28 C29 . . . . -137.8(2) ?
    C24 C19 C28 C29 . . . . 49.0(3) ?
    C28 N2 C27 C1 . . . . -166.90(17) ?
    C31 N2 C27 C1 . . . . 71.7(2) ?
    C28 N2 C27 C26 . . . . 64.4(2) ?
    C31 N2 C27 C26 . . . . -57.0(2) ?
    C32 C26 C27 N2 . . . . -59.7(2) ?
    C25 C26 C27 N2 . . . . 57.0(2) ?
    C32 C26 C27 C1 . . . . 173.74(17) ?
    C25 C26 C27 C1 . . . . -69.6(2) ?
    N1 C30 C29 C32 . . . . -51.9(2) ?
    C13 C30 C29 C32 . . . . 77.5(2) ?
    N1 C30 C29 C28 . . . . 62.5(2) ?
    C13 C30 C29 C28 . . . . -168.09(17) ?
    N2 C28 C29 C32 . . . . 61.9(2) ?
    C19 C28 C29 C32 . . . . -170.43(17) ?
    N2 C28 C29 C30 . . . . -56.7(2) ?
    C19 C28 C29 C30 . . . . 70.9(2) ?
    C25 C26 C32 O1 . . . . 125.4(2) ?
    C27 C26 C32 O1 . . . . -117.4(2) ?
    C25 C26 C32 C29 . . . . -57.3(2) ?
    C27 C26 C32 C29 . . . . 59.9(2) ?
    C30 C29 C32 O1 . . . . -127.1(2) ?
    C28 C29 C32 O1 . . . . 117.1(2) ?
    C30 C29 C32 C26 . . . . 55.6(2) ?
    C28 C29 C32 C26 . . . . -60.2(2) ?
    N2 C27 C1 C2 . . . . -140.8(2) ?
    C26 C27 C1 C2 . . . . -15.4(3) ?
    N2 C27 C1 C6 . . . . 43.4(3) ?
    C26 C27 C1 C6 . . . . 168.8(2) ?
    C18 C13 C14 C15 . . . . 3.2(3) ?
    C30 C13 C14 C15 . . . . -177.3(2) ?
    C6 C1 C2 C3 . . . . -1.6(4) ?
    C27 C1 C2 C3 . . . . -177.5(2) ?
    C8 C7 C12 C11 . . . . 2.2(3) ?
    C25 C7 C12 C11 . . . . -179.7(2) ?
    C8 C9 C10 C11 . . . . 2.2(4) ?
    C8 C9 C10 F1 . . . . -178.2(2) ?
    C9 C10 C11 C12 . . . . -2.4(4) ?
    F1 C10 C11 C12 . . . . 178.1(2) ?
    C7 C12 C11 C10 . . . . 0.1(4) ?
    C12 C7 C8 C9 . . . . -2.4(3) ?
    C25 C7 C8 C9 . . . . 179.6(2) ?
    C10 C9 C8 C7 . . . . 0.2(4) ?
    C14 C13 C18 C17 . . . . -3.3(3) ?
    C30 C13 C18 C17 . . . . 177.3(2) ?
    C20 C19 C24 C23 . . . . 2.0(3) ?
    C28 C19 C24 C23 . . . . 175.5(2) ?
    C24 C19 C20 C21 . . . . -2.4(3) ?
    C28 C19 C20 C21 . . . . -175.8(2) ?
    C15 C16 C17 C18 . . . . 0.7(4) ?
    F2 C16 C17 C18 . . . . -179.3(2) ?
    C13 C18 C17 C16 . . . . 1.4(4) ?
    C2 C1 C6 C5 . . . . 1.0(4) ?
    C27 C1 C6 C5 . . . . 177.1(2) ?
    C19 C24 C23 C22 . . . . -0.5(4) ?
    F2 C16 C15 C14 . . . . 179.3(2) ?
    C17 C16 C15 C14 . . . . -0.7(4) ?
    C13 C14 C15 C16 . . . . -1.3(4) ?
    C19 C20 C21 C22 . . . . 1.3(4) ?
    C20 C21 C22 C23 . . . . 0.3(4) ?
    C20 C21 C22 F4 . . . . 179.4(2) ?
    C24 C23 C22 C21 . . . . -0.7(4) ?
    C24 C23 C22 F4 . . . . -179.7(2) ?
    C3 C4 C5 C6 . . . . -1.8(4) ?
    F3 C4 C5 C6 . . . . 179.9(2) ?
    C1 C6 C5 C4 . . . . 0.7(4) ?
    C5 C4 C3 C2 . . . . 1.2(4) ?
    F3 C4 C3 C2 . . . . 179.5(2) ?
    C1 C2 C3 C4 . . . . 0.6(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C30 H30 O1 1_455 0.98 2.56 3.415(2) 146
