#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:05:30 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246786.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246786
loop_
_publ_author_name
'Prashanth, Jupally'
'Surov, Artem O.'
'Drozd, Ksenia V.'
'Perlovich, German L.'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Polymorphs, cocrystal and hydrate of nilutamide
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              3501
_journal_page_last               3513
_journal_paper_doi               10.1039/D3CE00328K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C12 H10 F3 N3 O4'
_chemical_formula_sum            'C12 H10 F3 N3 O4'
_chemical_formula_weight         317.23
_chemical_name_common            'Nilutamide Form IV'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-03-28 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.837(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.2681(13)
_cell_length_b                   34.536(4)
_cell_length_c                   9.8498(13)
_cell_measurement_reflns_used    6088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.36
_cell_volume                     4098.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1402
_diffrn_reflns_av_unetI/netI     0.1628
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            51343
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_min         2.061
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0076(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         8236
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0680P)²+0.9056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3765
_reflns_number_total             8236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00328k2.cif
_cod_data_source_block           KB426_0m
_cod_depositor_comments
'Adding full bibliography for 7246786--7246789.cif.'
_cod_original_cell_volume        4098.9(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246786
_shelx_shelxl_version_number     2019/2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.978
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'
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
C1A C 0.9627(3) 0.69222(13) 0.0728(4) 0.0299(10) Uani 1 1 d . . . . .
C2A C 0.8944(3) 0.66306(14) 0.0115(4) 0.0365(11) Uani 1 1 d . . . . .
H2A H 0.923276 0.642829 -0.036712 0.044 Uiso 1 1 calc R U . . .
C3A C 0.7835(3) 0.66343(13) 0.0206(4) 0.0349(11) Uani 1 1 d . . . . .
H3A H 0.735392 0.643413 -0.020980 0.042 Uiso 1 1 calc R U . . .
C4A C 0.7432(3) 0.69300(12) 0.0904(4) 0.0277(10) Uani 1 1 d . . . . .
C5A C 0.8108(3) 0.72318(13) 0.1488(4) 0.0309(11) Uani 1 1 d . . . . .
C6A C 0.9219(3) 0.72231(13) 0.1403(4) 0.0305(10) Uani 1 1 d . . . . .
H6A H 0.970014 0.742419 0.180936 0.037 Uiso 1 1 calc R U . . .
C7A C 0.7674(3) 0.75744(14) 0.2160(5) 0.0432(12) Uani 1 1 d . . . . .
C8A C 1.1519(3) 0.66496(15) 0.1490(4) 0.0374(12) Uani 1 1 d . . . . .
C9A C 1.2533(3) 0.69984(13) 0.0100(4) 0.0311(11) Uani 1 1 d . . . . .
C10A C 1.1311(3) 0.71141(13) -0.0216(4) 0.0320(11) Uani 1 1 d . . . . .
C11A C 1.2868(3) 0.68095(13) -0.1144(4) 0.0346(11) Uani 1 1 d . . . . .
H11A H 1.236368 0.659427 -0.146106 0.052 Uiso 1 1 calc R U . . .
H11B H 1.362897 0.671140 -0.089036 0.052 Uiso 1 1 calc R U . . .
H11C H 1.282959 0.700037 -0.188801 0.052 Uiso 1 1 calc R U . . .
C12A C 1.3241(3) 0.73502(14) 0.0604(5) 0.0539(14) Uani 1 1 d . . . . .
H12A H 1.320326 0.753647 -0.015407 0.081 Uiso 1 1 calc R U . . .
H12B H 1.401305 0.726904 0.091825 0.081 Uiso 1 1 calc R U . . .
H12C H 1.296409 0.747156 0.137181 0.081 Uiso 1 1 calc R U . . .
O1A O 0.5610(2) 0.68353(11) -0.0071(4) 0.0584(10) Uani 1 1 d . . . . .
O2A O 0.5999(2) 0.69669(10) 0.2118(4) 0.0511(9) Uani 1 1 d . . . . .
O3A O 1.1232(2) 0.64148(10) 0.2279(3) 0.0465(9) Uani 1 1 d . . . . .
O4A O 1.0880(2) 0.73404(9) -0.1093(3) 0.0423(8) Uani 1 1 d . . . . .
F1A F 0.66784(19) 0.76910(8) 0.1499(3) 0.0543(8) Uani 1 1 d . . . . .
F2A F 0.7592(2) 0.75106(9) 0.3471(3) 0.0644(9) Uani 1 1 d . . . . .
F3A F 0.8349(2) 0.78835(8) 0.2175(3) 0.0637(9) Uani 1 1 d . . . . .
N1B N 0.4694(3) 0.59131(11) 0.7584(4) 0.0374(9) Uani 1 1 d . . . . .
N2B N 0.8509(2) 0.62743(10) 0.5415(3) 0.0288(9) Uani 1 1 d . . . . .
N3B N 0.9606(3) 0.63331(10) 0.3891(4) 0.0312(9) Uani 1 1 d . . . . .
H3NB H 0.984(3) 0.6360(12) 0.311(4) 0.037 Uiso 1 1 d . U . . .
C1B C 0.7530(3) 0.61938(12) 0.5953(4) 0.0271(10) Uani 1 1 d . . . . .
C2B C 0.7603(3) 0.59502(12) 0.7069(4) 0.0324(11) Uani 1 1 d . . . . .
H2B H 0.829216 0.583489 0.746565 0.039 Uiso 1 1 calc R U . . .
C3B C 0.6664(3) 0.58743(13) 0.7611(4) 0.0327(11) Uani 1 1 d . . . . .
H3B H 0.670993 0.571208 0.839846 0.039 Uiso 1 1 calc R U . . .
C4B C 0.5662(3) 0.60347(12) 0.7006(4) 0.0294(10) Uani 1 1 d . . . . .
C5B C 0.5578(3) 0.62859(13) 0.5890(4) 0.0308(11) Uani 1 1 d . . . . .
C6B C 0.6532(3) 0.63681(12) 0.5376(4) 0.0296(10) Uani 1 1 d . . . . .
H6B H 0.650097 0.654404 0.462800 0.036 Uiso 1 1 calc R U . . .
C7B C 0.4525(3) 0.64896(15) 0.5274(5) 0.0392(12) Uani 1 1 d . . . . .
C8B C 0.8556(3) 0.62667(12) 0.3967(4) 0.0284(10) Uani 1 1 d . . . . .
C9B C 1.0339(3) 0.64016(13) 0.5211(4) 0.0289(11) Uani 1 1 d . . . . .
C10B C 0.9552(3) 0.63332(12) 0.6200(5) 0.0302(10) Uani 1 1 d . . . . .
C11B C 1.1293(3) 0.61127(14) 0.5487(4) 0.0411(12) Uani 1 1 d . . . . .
H11D H 1.099401 0.584933 0.547954 0.062 Uiso 1 1 calc R U . . .
H11E H 1.175525 0.616602 0.639233 0.062 Uiso 1 1 calc R U . . .
H11F H 1.174232 0.613669 0.476790 0.062 Uiso 1 1 calc R U . . .
C12B C 1.0742(3) 0.68224(14) 0.5321(4) 0.0425(12) Uani 1 1 d . . . . .
H12D H 1.127219 0.686259 0.470441 0.064 Uiso 1 1 calc R U . . .
H12E H 1.110370 0.687734 0.627573 0.064 Uiso 1 1 calc R U . . .
H12F H 1.010668 0.699641 0.505338 0.064 Uiso 1 1 calc R U . . .
N1A N 0.6255(3) 0.69119(11) 0.0989(5) 0.0412(10) Uani 1 1 d . . . . .
N2A N 1.0784(2) 0.69092(10) 0.0670(3) 0.0323(9) Uani 1 1 d . . . . .
N3A N 1.2528(3) 0.67178(12) 0.1202(4) 0.0378(10) Uani 1 1 d . . . . .
H3NA H 1.309(4) 0.6584(15) 0.146(5) 0.059(16) Uiso 1 1 d . . . . .
O1B O 0.4818(2) 0.58857(10) 0.8849(4) 0.0522(9) Uani 1 1 d . . . . .
O2B O 0.3850(2) 0.58325(10) 0.6790(3) 0.0509(9) Uani 1 1 d . . . . .
O3B O 0.7756(2) 0.62074(9) 0.3068(3) 0.0360(7) Uani 1 1 d . . . . .
O4B O 0.9800(2) 0.63293(9) 0.7450(3) 0.0374(8) Uani 1 1 d . . . . .
F1B F 0.39702(18) 0.66151(8) 0.6235(2) 0.0494(7) Uani 1 1 d . . . . .
F2B F 0.38225(19) 0.62667(9) 0.4404(2) 0.0525(8) Uani 1 1 d . . . . .
F3B F 0.47198(19) 0.68014(8) 0.4543(3) 0.0554(8) Uani 1 1 d . . . . .
C1C C 0.2890(3) 0.55456(12) 0.1582(4) 0.0282(10) Uani 1 1 d . . . . .
C2C C 0.2344(3) 0.57246(12) 0.0388(4) 0.0313(11) Uani 1 1 d . . . . .
H2C H 0.275416 0.585132 -0.020975 0.038 Uiso 1 1 calc R U . . .
C3C C 0.1208(3) 0.57176(12) 0.0074(4) 0.0310(10) Uani 1 1 d . . . . .
H3C H 0.082295 0.584200 -0.073595 0.037 Uiso 1 1 calc R U . . .
C4C C 0.0627(3) 0.55282(12) 0.0948(4) 0.0273(10) Uani 1 1 d . . . . .
C5C C 0.1152(3) 0.53458(12) 0.2147(4) 0.0263(10) Uani 1 1 d . . . . .
C6C C 0.2297(3) 0.53591(12) 0.2463(4) 0.0318(11) Uani 1 1 d . . . . .
H6C H 0.268154 0.524040 0.328469 0.038 Uiso 1 1 calc R U . . .
C7C C 0.0546(3) 0.51362(16) 0.3106(5) 0.0404(12) Uani 1 1 d D . . . .
C8C C 0.4710(3) 0.52235(14) 0.2321(4) 0.0301(10) Uani 1 1 d . . . . .
C9C C 0.5913(3) 0.53468(13) 0.2542(4) 0.0292(10) Uani 1 1 d . . . . .
C10C C 0.4746(3) 0.58829(14) 0.1908(4) 0.0295(10) Uani 1 1 d . . . . .
C11C C 0.6479(3) 0.51451(14) 0.1476(5) 0.0426(12) Uani 1 1 d . . . . .
H11G H 0.606868 0.520099 0.054366 0.064 Uiso 1 1 calc R U . . .
H11H H 0.648944 0.486491 0.163528 0.064 Uiso 1 1 calc R U . . .
H11I H 0.724221 0.524023 0.156677 0.064 Uiso 1 1 calc R U . . .
C12C C 0.6488(3) 0.52645(14) 0.4010(4) 0.0470(13) Uani 1 1 d . . . . .
H12G H 0.648526 0.498496 0.418054 0.070 Uiso 1 1 calc R U . . .
H12H H 0.609494 0.539756 0.465378 0.070 Uiso 1 1 calc R U . . .
H12I H 0.725526 0.535758 0.414748 0.070 Uiso 1 1 calc R U . . .
N1C N -0.0586(3) 0.55175(14) 0.0535(4) 0.0388(10) Uani 1 1 d D . . . .
N2C N 0.4067(2) 0.55465(10) 0.1918(3) 0.0275(8) Uani 1 1 d . . . . .
N3C N 0.5791(3) 0.57613(11) 0.2260(4) 0.0338(10) Uani 1 1 d . . . . .
H3NC H 0.632(3) 0.5918(12) 0.246(4) 0.030(12) Uiso 1 1 d . . . . .
O3C O 0.4369(2) 0.49005(9) 0.2469(3) 0.0403(8) Uani 1 1 d . . . . .
O4C O 0.4389(2) 0.62031(9) 0.1629(3) 0.0345(7) Uani 1 1 d . . . . .
F1C F 0.0044(8) 0.5355(3) 0.3874(9) 0.071(3) Uani 0.566(6) 1 d D . P A 1
F2C F 0.0302(5) 0.47779(16) 0.2776(6) 0.0469(16) Uani 0.566(6) 1 d D . P A 1
F3C F 0.1214(4) 0.5120(2) 0.4423(5) 0.0477(17) Uani 0.566(6) 1 d D . P A 1
O1C O -0.1089(4) 0.5774(2) -0.0001(8) 0.052(2) Uani 0.566(6) 1 d D . P A 1
O2C O -0.0988(4) 0.51711(16) 0.0615(5) 0.0410(19) Uani 0.566(6) 1 d D . P A 1
F11 F -0.0389(6) 0.5310(3) 0.3264(9) 0.031(2) Uani 0.434(6) 1 d D . P A 2
F21 F -0.0410(6) 0.4944(2) 0.2339(6) 0.043(2) Uani 0.434(6) 1 d D . P A 2
F31 F 0.1115(6) 0.4844(3) 0.3745(9) 0.055(3) Uani 0.434(6) 1 d D . P A 2
O11 O -0.1059(6) 0.5458(3) -0.0584(8) 0.048(3) Uani 0.434(6) 1 d D . P A 2
O21 O -0.1074(5) 0.5689(2) 0.1440(8) 0.053(3) Uani 0.434(6) 1 d D . P A 2
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'
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
C2A C1A C6A 121.2(4) . . ?
C2A C1A N2A 119.1(4) . . ?
C6A C1A N2A 119.7(4) . . ?
C1A C2A C3A 119.4(4) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
C4A C3A C2A 119.4(4) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C3A C4A C5A 121.5(3) . . ?
C3A C4A N1A 116.6(4) . . ?
C5A C4A N1A 121.8(4) . . ?
C6A C5A C4A 118.6(4) . . ?
C6A C5A C7A 118.6(4) . . ?
C4A C5A C7A 122.8(3) . . ?
C1A C6A C5A 119.9(4) . . ?
C1A C6A H6A 120.1 . . ?
C5A C6A H6A 120.1 . . ?
F2A C7A F1A 107.1(3) . . ?
F2A C7A F3A 106.2(4) . . ?
F1A C7A F3A 105.7(4) . . ?
F2A C7A C5A 113.2(4) . . ?
F1A C7A C5A 113.0(4) . . ?
F3A C7A C5A 111.1(3) . . ?
O3A C8A N3A 129.7(4) . . ?
O3A C8A N2A 123.8(4) . . ?
N3A C8A N2A 106.5(4) . . ?
N3A C9A C11A 110.9(4) . . ?
N3A C9A C12A 111.7(4) . . ?
C11A C9A C12A 112.5(3) . . ?
N3A C9A C10A 100.7(3) . . ?
C11A C9A C10A 110.7(3) . . ?
C12A C9A C10A 109.7(4) . . ?
O4A C10A N2A 126.2(4) . . ?
O4A C10A C9A 126.5(4) . . ?
N2A C10A C9A 107.2(4) . . ?
C9A C11A H11A 109.5 . . ?
C9A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C9A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C9A C12A H12A 109.5 . . ?
C9A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C9A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O2B N1B O1B 124.5(3) . . ?
O2B N1B C4B 118.1(4) . . ?
O1B N1B C4B 117.3(3) . . ?
C10B N2B C1B 125.2(3) . . ?
C10B N2B C8B 110.6(3) . . ?
C1B N2B C8B 123.9(3) . . ?
C8B N3B C9B 114.9(3) . . ?
C8B N3B H3NB 123(3) . . ?
C9B N3B H3NB 121(3) . . ?
C2B C1B C6B 120.9(3) . . ?
C2B C1B N2B 118.9(3) . . ?
C6B C1B N2B 120.2(4) . . ?
C1B C2B C3B 119.5(4) . . ?
C1B C2B H2B 120.3 . . ?
C3B C2B H2B 120.3 . . ?
C4B C3B C2B 119.8(4) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 121.4(3) . . ?
C3B C4B N1B 115.9(4) . . ?
C5B C4B N1B 122.7(3) . . ?
C4B C5B C6B 118.3(4) . . ?
C4B C5B C7B 123.0(3) . . ?
C6B C5B C7B 118.6(4) . . ?
C1B C6B C5B 120.1(4) . . ?
C1B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
F2B C7B F1B 106.7(3) . . ?
F2B C7B F3B 106.1(3) . . ?
F1B C7B F3B 106.6(4) . . ?
F2B C7B C5B 113.1(4) . . ?
F1B C7B C5B 112.4(3) . . ?
F3B C7B C5B 111.6(3) . . ?
O3B C8B N3B 130.7(4) . . ?
O3B C8B N2B 123.4(3) . . ?
N3B C8B N2B 105.9(3) . . ?
N3B C9B C10B 100.8(3) . . ?
N3B C9B C11B 112.2(3) . . ?
C10B C9B C11B 110.1(3) . . ?
N3B C9B C12B 110.7(3) . . ?
C10B C9B C12B 109.8(3) . . ?
C11B C9B C12B 112.5(3) . . ?
O4B C10B N2B 126.7(4) . . ?
O4B C10B C9B 126.0(3) . . ?
N2B C10B C9B 107.4(3) . . ?
C9B C11B H11D 109.5 . . ?
C9B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C9B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C9B C12B H12D 109.5 . . ?
C9B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C9B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O1A N1A O2A 125.2(3) . . ?
O1A N1A C4A 116.8(4) . . ?
O2A N1A C4A 118.0(4) . . ?
C10A N2A C8A 111.3(3) . . ?
C10A N2A C1A 126.6(3) . . ?
C8A N2A C1A 121.9(3) . . ?
C8A N3A C9A 114.0(4) . . ?
C8A N3A H3NA 126(3) . . ?
C9A N3A H3NA 118(3) . . ?
C2C C1C C6C 120.7(3) . . ?
C2C C1C N2C 120.4(3) . . ?
C6C C1C N2C 118.9(4) . . ?
C3C C2C C1C 119.5(4) . . ?
C3C C2C H2C 120.2 . . ?
C1C C2C H2C 120.2 . . ?
C2C C3C C4C 119.4(4) . . ?
C2C C3C H3C 120.3 . . ?
C4C C3C H3C 120.3 . . ?
C3C C4C C5C 122.3(3) . . ?
C3C C4C N1C 117.0(4) . . ?
C5C C4C N1C 120.6(3) . . ?
C6C C5C C4C 117.8(3) . . ?
C6C C5C C7C 118.7(4) . . ?
C4C C5C C7C 123.5(3) . . ?
C5C C6C C1C 120.3(4) . . ?
C5C C6C H6C 119.9 . . ?
C1C C6C H6C 119.9 . . ?
F2C C7C F1C 125.9(6) . . ?
F31 C7C F11 132.9(6) . . ?
F2C C7C F3C 105.0(5) . . ?
F1C C7C F3C 75.2(6) . . ?
F31 C7C F21 101.8(6) . . ?
F11 C7C F21 68.5(5) . . ?
F2C C7C C5C 115.0(4) . . ?
F1C C7C C5C 115.5(6) . . ?
F31 C7C C5C 113.0(4) . . ?
F11 C7C C5C 113.4(6) . . ?
F3C C7C C5C 109.3(4) . . ?
F21 C7C C5C 110.3(4) . . ?
O3C C8C N2C 126.0(4) . . ?
O3C C8C C9C 126.3(4) . . ?
N2C C8C C9C 107.7(4) . . ?
N3C C9C C12C 112.2(4) . . ?
N3C C9C C8C 100.7(3) . . ?
C12C C9C C8C 110.6(3) . . ?
N3C C9C C11C 111.1(3) . . ?
C12C C9C C11C 112.4(3) . . ?
C8C C9C C11C 109.2(3) . . ?
O4C C10C N3C 129.9(4) . . ?
O4C C10C N2C 124.1(4) . . ?
N3C C10C N2C 106.0(4) . . ?
C9C C11C H11G 109.5 . . ?
C9C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
C9C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C9C C12C H12G 109.5 . . ?
C9C C12C H12H 109.5 . . ?
H12G C12C H12H 109.5 . . ?
C9C C12C H12I 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
O1C N1C O2C 124.0(5) . . ?
O11 N1C O21 121.1(6) . . ?
O1C N1C C4C 122.4(5) . . ?
O11 N1C C4C 124.4(5) . . ?
O2C N1C C4C 112.5(4) . . ?
O21 N1C C4C 111.7(5) . . ?
C8C N2C C1C 124.5(3) . . ?
C8C N2C C10C 110.8(3) . . ?
C1C N2C C10C 124.6(3) . . ?
C10C N3C C9C 114.7(4) . . ?
C10C N3C H3NC 121(3) . . ?
C9C N3C H3NC 123(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.375(6) . ?
C1A C6A 1.378(5) . ?
C1A N2A 1.432(5) . ?
C2A C3A 1.381(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.374(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.387(6) . ?
C4A N1A 1.463(5) . ?
C5A C6A 1.382(5) . ?
C5A C7A 1.501(6) . ?
C6A H6A 0.9500 . ?
C7A F2A 1.333(5) . ?
C7A F1A 1.333(5) . ?
C7A F3A 1.349(5) . ?
C8A O3A 1.220(5) . ?
C8A N3A 1.342(5) . ?
C8A N2A 1.412(5) . ?
C9A N3A 1.456(5) . ?
C9A C11A 1.512(5) . ?
C9A C12A 1.522(6) . ?
C9A C10A 1.526(5) . ?
C10A O4A 1.211(5) . ?
C10A N2A 1.376(5) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O1A N1A 1.215(4) . ?
O2A N1A 1.226(4) . ?
N1B O2B 1.207(4) . ?
N1B O1B 1.230(4) . ?
N1B C4B 1.471(5) . ?
N2B C10B 1.380(5) . ?
N2B C1B 1.428(5) . ?
N2B C8B 1.438(5) . ?
N3B C8B 1.324(5) . ?
N3B C9B 1.455(5) . ?
N3B H3NB 0.87(4) . ?
C1B C2B 1.374(5) . ?
C1B C6B 1.387(5) . ?
C2B C3B 1.382(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.378(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.389(5) . ?
C5B C6B 1.389(5) . ?
C5B C7B 1.496(6) . ?
C6B H6B 0.9500 . ?
C7B F2B 1.338(5) . ?
C7B F1B 1.338(4) . ?
C7B F3B 1.341(5) . ?
C8B O3B 1.209(4) . ?
C9B C10B 1.514(5) . ?
C9B C11B 1.523(6) . ?
C9B C12B 1.532(6) . ?
C10B O4B 1.212(5) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
N3A H3NA 0.83(5) . ?
C1C C2C 1.385(5) . ?
C1C C6C 1.391(5) . ?
C1C N2C 1.419(5) . ?
C2C C3C 1.370(5) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.381(5) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.386(5) . ?
C4C N1C 1.467(5) . ?
C5C C6C 1.382(5) . ?
C5C C7C 1.494(6) . ?
C6C H6C 0.9500 . ?
C7C F2C 1.300(6) . ?
C7C F1C 1.303(8) . ?
C7C F31 1.318(7) . ?
C7C F11 1.330(10) . ?
C7C F3C 1.400(6) . ?
C7C F21 1.433(7) . ?
C8C O3C 1.210(5) . ?
C8C N2C 1.381(5) . ?
C8C C9C 1.512(5) . ?
C9C N3C 1.460(5) . ?
C9C C12C 1.512(6) . ?
C9C C11C 1.531(6) . ?
C10C O4C 1.202(5) . ?
C10C N3C 1.332(5) . ?
C10C N2C 1.431(5) . ?
C11C H11G 0.9800 . ?
C11C H11H 0.9800 . ?
C11C H11I 0.9800 . ?
C12C H12G 0.9800 . ?
C12C H12H 0.9800 . ?
C12C H12I 0.9800 . ?
N1C O1C 1.151(6) . ?
N1C O11 1.164(8) . ?
N1C O2C 1.302(6) . ?
N1C O21 1.306(7) . ?
N3C H3NC 0.84(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3A H3NA O4C 0.83(5) 2.05(5) 2.861(5) 167(5) 1_655 yes
N3B H3NB O3A 0.87(4) 2.04(4) 2.788(4) 143(4) . yes
N3C H3NC O3B 0.84(4) 2.02(4) 2.846(5) 169(4) . yes
C2A H2A O4B 0.95 2.41 3.180(5) 138.5 1_554 yes
C2A H2A O1C^a 0.95 2.33 2.959(9) 123.0 1_655 yes
C6A H6A O4A 0.95 2.43 3.258(5) 145.8 4_576 yes
C11A H11B O1A 0.98 2.45 3.332(5) 149.5 1_655 yes
C2B H2B O1C^a 0.95 2.48 3.087(8) 122.0 1_656 yes
C11B H11D F1C^a 0.98 2.47 3.286(10) 141.1 1_655 yes
C11B H11F O3A 0.98 2.60 3.316(5) 130.2 . yes
C3C H3C O4B 0.95 2.60 3.528(5) 165.8 1_454 yes
C11C H11I O2C^a 0.98 2.53 3.372(6) 143.6 1_655 yes
