##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-08-12
_journal_date_accepted     2011-08-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      9
_journal_page_first     o2381
_journal_page_last     o2382
_journal_paper_category     QO
_journal_coeditor_code     WN2449
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;\
4'-[5-(4-Fluorophenyl)pyridin-3-yl]-1'-methyldispiro[indan-2,2'-pyrrolidine-3',\
2''-indan]-1,3,1''-trione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ang Chee Wei' ?
;
     Institute for Research in Molecular Medicine
     Universiti Sains Malaysia
     11800 USM, Penang
     Malaysia
;
    'Mohamed Ashraf Ali' ?
;
     Institute for Research in Molecular Medicine
     Universiti Sains Malaysia
     11800 USM, Penang
     Malaysia
;
    'Rusli Ismail' ?
;
     Institute for Research in Molecular Medicine
     Universiti Sains Malaysia
     11800 USM, Penang
     Malaysia
;
    'Ching Kheng Quah'
;
      Thomson Reuters ResearcherID: A-5525-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4'-[5-(4-Fluorophenyl)pyridin-3-yl]-1'-methyldispiro[indan-2,2'-pyrrolidine-
3',2''-indan]-1,3,1''-trione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H23 F N2 O3'
_chemical_formula_sum     'C32 H23 F N2 O3'
_chemical_formula_iupac     'C32 H23 F N2 O3'
_chemical_formula_weight     502.52
_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     14.8997(2)
_cell_length_b     7.79930(10)
_cell_length_c     23.0188(3)
_cell_angle_alpha     90.00
_cell_angle_beta     112.6380(10)
_cell_angle_gamma     90.00
_cell_volume     2468.86(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5035
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     28.09
_cell_measurement_temperature     100
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.359
_exptl_crystal_size_mid     0.166
_exptl_crystal_size_min     0.049
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1048
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9676
_exptl_absorpt_correction_T_max     0.9955
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0 (1) K.
;
_diffrn_ambient_temperature     100
_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
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     27325
_diffrn_reflns_av_R_equivalents     0.0565
_diffrn_reflns_av_sigmaI/netI     0.0710
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     30.09
_diffrn_reflns_theta_full     30.09
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     32
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 > 2sigma(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     7184
_reflns_number_gt     4664
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0936
_refine_ls_R_factor_gt     0.0533
_refine_ls_wR_factor_gt     0.1156
_refine_ls_wR_factor_ref     0.1353
_refine_ls_goodness_of_fit_ref     0.993
_refine_ls_restrained_S_all     0.993
_refine_ls_number_reflns     7184
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0641P)²+0.0000P] 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     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.286
_refine_diff_density_min     -0.271
_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'
    '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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 -0.02526(8) 0.88163(14) 0.42880(5) 0.0352(3) Uani d . 1 1 . .
    O O1 0.53116(8) 0.12559(15) 0.85281(6) 0.0203(3) Uani d . 1 1 . .
    O O2 0.22158(9) 0.20148(15) 0.85535(6) 0.0212(3) Uani d . 1 1 . .
    O O3 0.38943(8) -0.17977(14) 0.76020(6) 0.0187(3) Uani d . 1 1 . .
    N N1 0.35687(10) 0.35355(16) 0.80293(6) 0.0142(3) Uani d . 1 1 . .
    N N2 0.30185(11) 0.07049(18) 0.54724(7) 0.0200(3) Uani d . 1 1 . .
    C C1 0.35388(12) 0.17247(19) 0.81705(7) 0.0133(3) Uani d . 1 1 . .
    C C2 0.45362(12) 0.08860(19) 0.85599(8) 0.0146(3) Uani d . 1 1 . .
    C C3 0.43827(12) -0.03372(19) 0.90018(7) 0.0144(3) Uani d . 1 1 . .
    C C4 0.50353(13) -0.1516(2) 0.93975(8) 0.0180(4) Uani d . 1 1 . .
    H H4A 0.5677 -0.1626 0.9409 0.022 Uiso calc R 1 1 . .
    C C5 0.47110(14) -0.2526(2) 0.97738(8) 0.0206(4) Uani d . 1 1 . .
    H H5A 0.5142 -0.3338 1.0050 0.025 Uiso calc R 1 1 . .
    C C6 0.37646(14) -0.2379(2) 0.97576(8) 0.0232(4) Uani d . 1 1 . .
    H H6A 0.3560 -0.3103 1.0015 0.028 Uiso calc R 1 1 . .
    C C7 0.31210(13) -0.1179(2) 0.93668(8) 0.0202(4) Uani d . 1 1 . .
    H H7A 0.2481 -0.1062 0.9357 0.024 Uiso calc R 1 1 . .
    C C8 0.34458(12) -0.0158(2) 0.89913(7) 0.0153(3) Uani d . 1 1 . .
    C C9 0.29442(12) 0.1276(2) 0.85693(8) 0.0158(3) Uani d . 1 1 . .
    C C10 0.30739(11) 0.09841(19) 0.74827(8) 0.0130(3) Uani d . 1 1 . .
    C C11 0.31431(12) -0.09919(19) 0.74843(7) 0.0140(3) Uani d . 1 1 . .
    C C12 0.21613(12) -0.1679(2) 0.73393(8) 0.0155(3) Uani d . 1 1 . .
    C C13 0.18807(12) -0.3386(2) 0.73650(8) 0.0178(4) Uani d . 1 1 . .
    H H13A 0.2347 -0.4285 0.7487 0.021 Uiso calc R 1 1 . .
    C C14 0.09024(13) -0.3714(2) 0.72068(9) 0.0224(4) Uani d . 1 1 . .
    H H14A 0.0692 -0.4855 0.7225 0.027 Uiso calc R 1 1 . .
    C C15 0.02184(13) -0.2386(2) 0.70207(9) 0.0225(4) Uani d . 1 1 . .
    H H15A -0.0451 -0.2643 0.6909 0.027 Uiso calc R 1 1 . .
    C C16 0.05016(12) -0.0699(2) 0.69970(8) 0.0191(4) Uani d . 1 1 . .
    H H16A 0.0033 0.0196 0.6867 0.023 Uiso calc R 1 1 . .
    C C17 0.14895(12) -0.0346(2) 0.71677(7) 0.0150(3) Uani d . 1 1 . .
    C C18 0.19694(11) 0.1362(2) 0.71821(8) 0.0155(3) Uani d . 1 1 . .
    H H18A 0.1781 0.2198 0.7439 0.019 Uiso calc R 1 1 . .
    H H18B 0.1785 0.1826 0.6751 0.019 Uiso calc R 1 1 . .
    C C19 0.37211(12) 0.19184(19) 0.71845(8) 0.0137(3) Uani d . 1 1 . .
    H H19A 0.4335 0.1243 0.7297 0.016 Uiso calc R 1 1 . .
    C C20 0.39874(12) 0.3643(2) 0.75442(8) 0.0156(3) Uani d . 1 1 . .
    H H20A 0.4702 0.3790 0.7741 0.019 Uiso calc R 1 1 . .
    H H20B 0.3704 0.4618 0.7257 0.019 Uiso calc R 1 1 . .
    C C21 0.40153(13) 0.4657(2) 0.85715(8) 0.0187(4) Uani d . 1 1 . .
    H H21A 0.3638 0.4615 0.8838 0.028 Uiso calc R 1 1 . .
    H H21B 0.4026 0.5836 0.8427 0.028 Uiso calc R 1 1 . .
    H H21C 0.4682 0.4275 0.8814 0.028 Uiso calc R 1 1 . .
    C C22 0.32635(12) 0.2035(2) 0.64733(8) 0.0150(3) Uani d . 1 1 . .
    C C23 0.33944(12) 0.0714(2) 0.61049(8) 0.0171(3) Uani d . 1 1 . .
    H H23A 0.3775 -0.0243 0.6315 0.021 Uiso calc R 1 1 . .
    C C24 0.24663(12) 0.2045(2) 0.51798(8) 0.0185(4) Uani d . 1 1 . .
    H H24A 0.2200 0.2059 0.4733 0.022 Uiso calc R 1 1 . .
    C C25 0.22608(12) 0.3425(2) 0.54969(8) 0.0157(3) Uani d . 1 1 . .
    C C26 0.26802(12) 0.3398(2) 0.61536(8) 0.0157(3) Uani d . 1 1 . .
    H H26A 0.2566 0.4323 0.6385 0.019 Uiso calc R 1 1 . .
    C C27 0.16180(12) 0.4862(2) 0.51584(8) 0.0170(3) Uani d . 1 1 . .
    C C28 0.08191(13) 0.4584(2) 0.45942(8) 0.0207(4) Uani d . 1 1 . .
    H H28A 0.0704 0.3471 0.4412 0.025 Uiso calc R 1 1 . .
    C C29 0.01936(13) 0.5917(2) 0.42980(9) 0.0247(4) Uani d . 1 1 . .
    H H29A -0.0349 0.5731 0.3915 0.030 Uiso calc R 1 1 . .
    C C30 0.03784(13) 0.7509(2) 0.45716(9) 0.0246(4) Uani d . 1 1 . .
    C C31 0.11572(13) 0.7859(2) 0.51189(9) 0.0239(4) Uani d . 1 1 . .
    H H31A 0.1265 0.8982 0.5292 0.029 Uiso calc R 1 1 . .
    C C32 0.17830(13) 0.6522(2) 0.54108(8) 0.0210(4) Uani d . 1 1 . .
    H H32A 0.2332 0.6735 0.5788 0.025 Uiso calc R 1 1 . .
_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 C30 . 1.3702(19) ?
    O1 C2 . 1.2200(19) ?
    O2 C9 . 1.2170(19) ?
    O3 C11 . 1.2196(19) ?
    N1 C1 . 1.4537(19) ?
    N1 C21 . 1.458(2) ?
    N1 C20 . 1.476(2) ?
    N2 C24 . 1.341(2) ?
    N2 C23 . 1.344(2) ?
    C1 C9 . 1.541(2) ?
    C1 C2 . 1.554(2) ?
    C1 C10 . 1.574(2) ?
    C2 C3 . 1.475(2) ?
    C3 C4 . 1.393(2) ?
    C3 C8 . 1.394(2) ?
    C4 C5 . 1.388(2) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.401(3) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.393(2) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.392(2) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.481(2) ?
    C10 C11 . 1.545(2) ?
    C10 C18 . 1.548(2) ?
    C10 C19 . 1.562(2) ?
    C11 C12 . 1.471(2) ?
    C12 C17 . 1.391(2) ?
    C12 C13 . 1.403(2) ?
    C13 C14 . 1.384(2) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.399(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.390(2) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.397(2) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.506(2) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C22 . 1.515(2) ?
    C19 C20 . 1.549(2) ?
    C19 H19A . 1.0000 ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 C26 . 1.391(2) ?
    C22 C23 . 1.395(2) ?
    C23 H23A . 0.9500 ?
    C24 C25 . 1.399(2) ?
    C24 H24A . 0.9500 ?
    C25 C26 . 1.396(2) ?
    C25 C27 . 1.485(2) ?
    C26 H26A . 0.9500 ?
    C27 C28 . 1.400(2) ?
    C27 C32 . 1.401(2) ?
    C28 C29 . 1.388(2) ?
    C28 H28A . 0.9500 ?
    C29 C30 . 1.371(3) ?
    C29 H29A . 0.9500 ?
    C30 C31 . 1.372(3) ?
    C31 C32 . 1.388(2) ?
    C31 H31A . 0.9500 ?
    C32 H32A . 0.9500 ?
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
    C1 N1 C21 . . 115.76(13) ?
    C1 N1 C20 . . 106.41(12) ?
    C21 N1 C20 . . 115.26(13) ?
    C24 N2 C23 . . 117.35(15) ?
    N1 C1 C9 . . 115.33(13) ?
    N1 C1 C2 . . 115.67(13) ?
    C9 C1 C2 . . 101.66(12) ?
    N1 C1 C10 . . 99.85(12) ?
    C9 C1 C10 . . 112.61(13) ?
    C2 C1 C10 . . 112.26(12) ?
    O1 C2 C3 . . 126.58(15) ?
    O1 C2 C1 . . 125.69(15) ?
    C3 C2 C1 . . 107.60(13) ?
    C4 C3 C8 . . 121.34(15) ?
    C4 C3 C2 . . 128.58(16) ?
    C8 C3 C2 . . 110.06(14) ?
    C5 C4 C3 . . 117.37(17) ?
    C5 C4 H4A . . 121.3 ?
    C3 C4 H4A . . 121.3 ?
    C4 C5 C6 . . 121.71(16) ?
    C4 C5 H5A . . 119.1 ?
    C6 C5 H5A . . 119.1 ?
    C7 C6 C5 . . 120.53(16) ?
    C7 C6 H6A . . 119.7 ?
    C5 C6 H6A . . 119.7 ?
    C8 C7 C6 . . 117.91(16) ?
    C8 C7 H7A . . 121.0 ?
    C6 C7 H7A . . 121.0 ?
    C7 C8 C3 . . 121.11(15) ?
    C7 C8 C9 . . 129.14(16) ?
    C3 C8 C9 . . 109.66(14) ?
    O2 C9 C8 . . 126.60(15) ?
    O2 C9 C1 . . 125.80(15) ?
    C8 C9 C1 . . 107.55(13) ?
    C11 C10 C18 . . 104.44(12) ?
    C11 C10 C19 . . 114.49(13) ?
    C18 C10 C19 . . 116.40(13) ?
    C11 C10 C1 . . 111.14(13) ?
    C18 C10 C1 . . 111.13(13) ?
    C19 C10 C1 . . 99.42(12) ?
    O3 C11 C12 . . 127.60(15) ?
    O3 C11 C10 . . 124.71(15) ?
    C12 C11 C10 . . 107.67(13) ?
    C17 C12 C13 . . 121.85(15) ?
    C17 C12 C11 . . 109.63(14) ?
    C13 C12 C11 . . 128.51(15) ?
    C14 C13 C12 . . 117.71(16) ?
    C14 C13 H13A . . 121.1 ?
    C12 C13 H13A . . 121.1 ?
    C13 C14 C15 . . 120.88(16) ?
    C13 C14 H14A . . 119.6 ?
    C15 C14 H14A . . 119.6 ?
    C16 C15 C14 . . 121.10(16) ?
    C16 C15 H15A . . 119.5 ?
    C14 C15 H15A . . 119.5 ?
    C15 C16 C17 . . 118.59(16) ?
    C15 C16 H16A . . 120.7 ?
    C17 C16 H16A . . 120.7 ?
    C12 C17 C16 . . 119.84(15) ?
    C12 C17 C18 . . 111.79(14) ?
    C16 C17 C18 . . 128.35(15) ?
    C17 C18 C10 . . 104.82(12) ?
    C17 C18 H18A . . 110.8 ?
    C10 C18 H18A . . 110.8 ?
    C17 C18 H18B . . 110.8 ?
    C10 C18 H18B . . 110.8 ?
    H18A C18 H18B . . 108.9 ?
    C22 C19 C20 . . 116.22(13) ?
    C22 C19 C10 . . 113.93(13) ?
    C20 C19 C10 . . 104.16(13) ?
    C22 C19 H19A . . 107.4 ?
    C20 C19 H19A . . 107.4 ?
    C10 C19 H19A . . 107.4 ?
    N1 C20 C19 . . 105.02(12) ?
    N1 C20 H20A . . 110.7 ?
    C19 C20 H20A . . 110.7 ?
    N1 C20 H20B . . 110.7 ?
    C19 C20 H20B . . 110.7 ?
    H20A C20 H20B . . 108.8 ?
    N1 C21 H21A . . 109.5 ?
    N1 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    N1 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C26 C22 C23 . . 116.61(15) ?
    C26 C22 C19 . . 123.18(14) ?
    C23 C22 C19 . . 120.18(14) ?
    N2 C23 C22 . . 124.41(16) ?
    N2 C23 H23A . . 117.8 ?
    C22 C23 H23A . . 117.8 ?
    N2 C24 C25 . . 123.58(16) ?
    N2 C24 H24A . . 118.2 ?
    C25 C24 H24A . . 118.2 ?
    C26 C25 C24 . . 117.20(15) ?
    C26 C25 C27 . . 120.58(15) ?
    C24 C25 C27 . . 122.22(15) ?
    C22 C26 C25 . . 120.82(15) ?
    C22 C26 H26A . . 119.6 ?
    C25 C26 H26A . . 119.6 ?
    C28 C27 C32 . . 118.59(16) ?
    C28 C27 C25 . . 121.06(15) ?
    C32 C27 C25 . . 120.32(15) ?
    C29 C28 C27 . . 120.67(17) ?
    C29 C28 H28A . . 119.7 ?
    C27 C28 H28A . . 119.7 ?
    C30 C29 C28 . . 118.33(17) ?
    C30 C29 H29A . . 120.8 ?
    C28 C29 H29A . . 120.8 ?
    F1 C30 C29 . . 118.38(16) ?
    F1 C30 C31 . . 118.15(17) ?
    C29 C30 C31 . . 123.47(17) ?
    C30 C31 C32 . . 117.89(17) ?
    C30 C31 H31A . . 121.1 ?
    C32 C31 H31A . . 121.1 ?
    C31 C32 C27 . . 121.03(17) ?
    C31 C32 H32A . . 119.5 ?
    C27 C32 H32A . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C21 N1 C1 C9 . . . . 62.03(19) ?
    C20 N1 C1 C9 . . . . -168.47(13) ?
    C21 N1 C1 C2 . . . . -56.37(19) ?
    C20 N1 C1 C2 . . . . 73.13(16) ?
    C21 N1 C1 C10 . . . . -177.04(13) ?
    C20 N1 C1 C10 . . . . -47.54(15) ?
    N1 C1 C2 O1 . . . . -34.0(2) ?
    C9 C1 C2 O1 . . . . -159.71(16) ?
    C10 C1 C2 O1 . . . . 79.72(19) ?
    N1 C1 C2 C3 . . . . 142.07(13) ?
    C9 C1 C2 C3 . . . . 16.34(16) ?
    C10 C1 C2 C3 . . . . -104.23(15) ?
    O1 C2 C3 C4 . . . . -11.5(3) ?
    C1 C2 C3 C4 . . . . 172.51(15) ?
    O1 C2 C3 C8 . . . . 167.33(16) ?
    C1 C2 C3 C8 . . . . -8.67(18) ?
    C8 C3 C4 C5 . . . . 1.0(2) ?
    C2 C3 C4 C5 . . . . 179.71(16) ?
    C3 C4 C5 C6 . . . . 0.3(2) ?
    C4 C5 C6 C7 . . . . -1.2(3) ?
    C5 C6 C7 C8 . . . . 0.8(3) ?
    C6 C7 C8 C3 . . . . 0.5(2) ?
    C6 C7 C8 C9 . . . . -175.63(16) ?
    C4 C3 C8 C7 . . . . -1.4(2) ?
    C2 C3 C8 C7 . . . . 179.65(15) ?
    C4 C3 C8 C9 . . . . 175.39(14) ?
    C2 C3 C8 C9 . . . . -3.53(18) ?
    C7 C8 C9 O2 . . . . 13.4(3) ?
    C3 C8 C9 O2 . . . . -163.05(16) ?
    C7 C8 C9 C1 . . . . -169.08(16) ?
    C3 C8 C9 C1 . . . . 14.43(18) ?
    N1 C1 C9 O2 . . . . 33.2(2) ?
    C2 C1 C9 O2 . . . . 159.15(16) ?
    C10 C1 C9 O2 . . . . -80.52(19) ?
    N1 C1 C9 C8 . . . . -144.31(14) ?
    C2 C1 C9 C8 . . . . -18.35(16) ?
    C10 C1 C9 C8 . . . . 101.97(15) ?
    N1 C1 C10 C11 . . . . 168.49(13) ?
    C9 C1 C10 C11 . . . . -68.64(16) ?
    C2 C1 C10 C11 . . . . 45.39(17) ?
    N1 C1 C10 C18 . . . . -75.66(15) ?
    C9 C1 C10 C18 . . . . 47.21(17) ?
    C2 C1 C10 C18 . . . . 161.23(13) ?
    N1 C1 C10 C19 . . . . 47.52(14) ?
    C9 C1 C10 C19 . . . . 170.39(12) ?
    C2 C1 C10 C19 . . . . -75.59(14) ?
    C18 C10 C11 O3 . . . . 169.18(15) ?
    C19 C10 C11 O3 . . . . 40.7(2) ?
    C1 C10 C11 O3 . . . . -70.9(2) ?
    C18 C10 C11 C12 . . . . -12.43(17) ?
    C19 C10 C11 C12 . . . . -140.87(14) ?
    C1 C10 C11 C12 . . . . 107.48(15) ?
    O3 C11 C12 C17 . . . . -173.71(16) ?
    C10 C11 C12 C17 . . . . 7.96(18) ?
    O3 C11 C12 C13 . . . . 7.1(3) ?
    C10 C11 C12 C13 . . . . -171.27(16) ?
    C17 C12 C13 C14 . . . . 0.6(3) ?
    C11 C12 C13 C14 . . . . 179.77(16) ?
    C12 C13 C14 C15 . . . . 0.8(3) ?
    C13 C14 C15 C16 . . . . -0.8(3) ?
    C14 C15 C16 C17 . . . . -0.4(3) ?
    C13 C12 C17 C16 . . . . -1.9(3) ?
    C11 C12 C17 C16 . . . . 178.80(15) ?
    C13 C12 C17 C18 . . . . 179.42(15) ?
    C11 C12 C17 C18 . . . . 0.13(19) ?
    C15 C16 C17 C12 . . . . 1.8(2) ?
    C15 C16 C17 C18 . . . . -179.80(16) ?
    C12 C17 C18 C10 . . . . -8.03(18) ?
    C16 C17 C18 C10 . . . . 173.44(16) ?
    C11 C10 C18 C17 . . . . 12.09(16) ?
    C19 C10 C18 C17 . . . . 139.37(14) ?
    C1 C10 C18 C17 . . . . -107.82(14) ?
    C11 C10 C19 C22 . . . . 82.84(17) ?
    C18 C10 C19 C22 . . . . -39.30(19) ?
    C1 C10 C19 C22 . . . . -158.66(13) ?
    C11 C10 C19 C20 . . . . -149.54(13) ?
    C18 C10 C19 C20 . . . . 88.32(16) ?
    C1 C10 C19 C20 . . . . -31.03(14) ?
    C1 N1 C20 C19 . . . . 27.63(16) ?
    C21 N1 C20 C19 . . . . 157.41(13) ?
    C22 C19 C20 N1 . . . . 130.35(14) ?
    C10 C19 C20 N1 . . . . 4.16(16) ?
    C20 C19 C22 C26 . . . . -31.0(2) ?
    C10 C19 C22 C26 . . . . 90.10(18) ?
    C20 C19 C22 C23 . . . . 150.83(15) ?
    C10 C19 C22 C23 . . . . -88.05(18) ?
    C24 N2 C23 C22 . . . . -1.3(2) ?
    C26 C22 C23 N2 . . . . 1.8(2) ?
    C19 C22 C23 N2 . . . . -179.93(15) ?
    C23 N2 C24 C25 . . . . -0.5(2) ?
    N2 C24 C25 C26 . . . . 1.6(2) ?
    N2 C24 C25 C27 . . . . -177.84(15) ?
    C23 C22 C26 C25 . . . . -0.5(2) ?
    C19 C22 C26 C25 . . . . -178.74(15) ?
    C24 C25 C26 C22 . . . . -1.0(2) ?
    C27 C25 C26 C22 . . . . 178.41(15) ?
    C26 C25 C27 C28 . . . . -145.25(17) ?
    C24 C25 C27 C28 . . . . 34.2(2) ?
    C26 C25 C27 C32 . . . . 32.6(2) ?
    C24 C25 C27 C32 . . . . -147.97(17) ?
    C32 C27 C28 C29 . . . . -1.2(3) ?
    C25 C27 C28 C29 . . . . 176.67(16) ?
    C27 C28 C29 C30 . . . . 0.0(3) ?
    C28 C29 C30 F1 . . . . -178.37(16) ?
    C28 C29 C30 C31 . . . . 0.9(3) ?
    F1 C30 C31 C32 . . . . 178.73(16) ?
    C29 C30 C31 C32 . . . . -0.6(3) ?
    C30 C31 C32 C27 . . . . -0.7(3) ?
    C28 C27 C32 C31 . . . . 1.6(3) ?
    C25 C27 C32 C31 . . . . -176.31(16) ?
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
    _geom_hbond_publ_flag
    C6 H6A N2 4_556 0.95 2.56 3.476(2) 163 yes
    C13 H13A N1 1_545 0.95 2.45 3.387(2) 168 yes
    C15 H15A O2 2_546 0.95 2.44 3.381(3) 169 yes
    C18 H18A O2 . 0.99 2.40 3.077(2) 125 yes
    C20 H20A O3 2_656 0.99 2.55 3.318(2) 135 yes
    C4 H4A Cg1 2_646 0.95 2.65 3.552(2) 159 yes
