# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB426_0m
_database_code_depnum_ccdc_archive 'CCDC 2252217'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-03-28 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Nilutamide Form IV'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 N3 O4'
_chemical_formula_sum            'C12 H10 F3 N3 O4'
_chemical_formula_weight         317.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.2681(13)
_cell_length_b                   34.536(4)
_cell_length_c                   9.8498(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.837(5)
_cell_angle_gamma                90
_cell_volume                     4098.9(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6088
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      20.85

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             1944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5894
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?


_diffrn_reflns_number            51343
_diffrn_reflns_av_unetI/netI     0.1628
_diffrn_reflns_av_R_equivalents  0.1402
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.061
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8236
_reflns_number_gt                3765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.9056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0076(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8236
_refine_ls_number_parameters     659
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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


_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_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_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_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

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.065

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB391_0m
_database_code_depnum_ccdc_archive 'CCDC 2252218'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-03-28 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Nilutamide- Form V'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 N3 O4'
_chemical_formula_sum            'C12 H10 F3 N3 O4'
_chemical_formula_weight         317.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1966(5)
_cell_length_b                   16.2038(12)
_cell_length_c                   22.6209(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.633(2)
_cell_angle_gamma                90
_cell_volume                     2629.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3913
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6351
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;



_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?


_diffrn_reflns_number            26240
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5290
_reflns_number_gt                3029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5290
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.7759(3) 0.77773(14) 0.63054(10) 0.0192(5) Uani 1 1 d . . . . .
C2A C 0.8054(3) 0.82075(15) 0.57920(10) 0.0213(6) Uani 1 1 d . . . . .
H2A H 0.810095 0.879340 0.579587 0.026 Uiso 1 1 calc R U . . .
C3A C 0.8279(3) 0.77791(15) 0.52738(10) 0.0228(6) Uani 1 1 d . . . . .
H3A H 0.851820 0.806950 0.492307 0.027 Uiso 1 1 calc R U . . .
C4A C 0.8157(3) 0.69297(14) 0.52670(10) 0.0212(6) Uani 1 1 d . . . . .
C5A C 0.7879(3) 0.64840(14) 0.57774(10) 0.0202(5) Uani 1 1 d . . . . .
C6A C 0.7693(3) 0.69164(14) 0.62985(10) 0.0190(5) Uani 1 1 d . . . . .
H6A H 0.751916 0.662406 0.665390 0.023 Uiso 1 1 calc R U . . .
C7A C 0.7909(3) 0.55579(15) 0.58086(11) 0.0246(6) Uani 1 1 d . . . . .
C8A C 0.6639(3) 0.79119(14) 0.73188(10) 0.0187(5) Uani 1 1 d . . . . .
C9A C 0.6729(3) 0.85718(14) 0.77940(10) 0.0217(6) Uani 1 1 d . . . . .
C10A C 0.8473(3) 0.89616(14) 0.70083(11) 0.0210(6) Uani 1 1 d . . . . .
C11A C 0.7678(3) 0.82442(14) 0.83690(10) 0.0238(6) Uani 1 1 d . . . . .
H11A H 0.695628 0.778163 0.851013 0.036 Uiso 1 1 calc R U . . .
H11B H 0.775498 0.868377 0.866758 0.036 Uiso 1 1 calc R U . . .
H11C H 0.893713 0.805541 0.830124 0.036 Uiso 1 1 calc R U . . .
C12A C 0.4737(3) 0.88690(15) 0.78601(11) 0.0258(6) Uani 1 1 d . . . . .
H12A H 0.421491 0.910428 0.748352 0.039 Uiso 1 1 calc R U . . .
H12B H 0.475155 0.929093 0.817085 0.039 Uiso 1 1 calc R U . . .
H12C H 0.396805 0.840194 0.796835 0.039 Uiso 1 1 calc R U . . .
N1A N 0.8280(3) 0.65216(13) 0.46904(9) 0.0277(5) Uani 1 1 d . . . . .
N2A N 0.7531(2) 0.82118(11) 0.68404(8) 0.0178(4) Uani 1 1 d . . . . .
N3A N 0.7881(3) 0.91948(13) 0.75299(9) 0.0216(5) Uani 1 1 d . . . . .
H3AA H 0.856(3) 0.9538(16) 0.7734(11) 0.033(8) Uiso 1 1 d . . . . .
O1A O 0.9434(2) 0.67903(11) 0.43677(7) 0.0352(5) Uani 1 1 d . . . . .
O2A O 0.7203(2) 0.59490(11) 0.45598(8) 0.0369(5) Uani 1 1 d . . . . .
O3A O 0.5865(2) 0.72499(10) 0.73487(7) 0.0238(4) Uani 1 1 d . . . . .
O4A O 0.9595(2) 0.93036(9) 0.67136(7) 0.0259(4) Uani 1 1 d . . . . .
F1A F 0.92422(18) 0.52305(8) 0.55001(6) 0.0327(4) Uani 1 1 d . . . . .
F2A F 0.63047(18) 0.51971(8) 0.56158(6) 0.0313(4) Uani 1 1 d . . . . .
F3A F 0.82834(19) 0.53030(8) 0.63728(6) 0.0320(4) Uani 1 1 d . . . . .
C1B C 1.2293(3) 1.18236(14) 0.86320(10) 0.0194(5) Uani 1 1 d . . . . .
C2B C 1.2090(3) 1.13192(14) 0.91200(10) 0.0225(6) Uani 1 1 d . . . . .
H2B H 1.213799 1.073607 0.908090 0.027 Uiso 1 1 calc R U . . .
C3B C 1.1817(3) 1.16743(15) 0.96651(11) 0.0239(6) Uani 1 1 d . . . . .
H3B H 1.162520 1.133530 0.999739 0.029 Uiso 1 1 calc R U . . .
C4B C 1.1825(3) 1.25214(15) 0.97209(10) 0.0230(6) Uani 1 1 d . . . . .
C5B C 1.2052(3) 1.30357(14) 0.92409(11) 0.0214(6) Uani 1 1 d . . . . .
C6B C 1.2275(3) 1.26773(14) 0.86926(10) 0.0207(6) Uani 1 1 d . . . . .
H6B H 1.241717 1.301786 0.835738 0.025 Uiso 1 1 calc R U . . .
C7B C 1.1941(3) 1.39623(15) 0.92808(11) 0.0274(6) Uani 1 1 d . . . . .
C8B C 1.3343(3) 1.18280(14) 0.76042(10) 0.0192(5) Uani 1 1 d . . . . .
C9B C 1.3133(3) 1.12423(13) 0.70776(10) 0.0207(6) Uani 1 1 d . . . . .
C10B C 1.1499(3) 1.07434(14) 0.78599(11) 0.0210(6) Uani 1 1 d . . . . .
C11B C 1.5072(3) 1.09455(15) 0.69465(12) 0.0291(6) Uani 1 1 d . . . . .
H11D H 1.496017 1.054612 0.662021 0.044 Uiso 1 1 calc R U . . .
H11E H 1.568114 1.068237 0.730108 0.044 Uiso 1 1 calc R U . . .
H11F H 1.581891 1.141742 0.683414 0.044 Uiso 1 1 calc R U . . .
C12B C 1.2120(3) 1.16592(15) 0.65388(10) 0.0274(6) Uani 1 1 d . . . . .
H12D H 1.284654 1.213520 0.642175 0.041 Uiso 1 1 calc R U . . .
H12E H 1.088843 1.184478 0.663916 0.041 Uiso 1 1 calc R U . . .
H12F H 1.197561 1.126543 0.620947 0.041 Uiso 1 1 calc R U . . .
N1B N 1.1620(3) 1.28612(13) 1.03171(9) 0.0288(5) Uani 1 1 d . . . . .
N2B N 1.2491(2) 1.14626(11) 0.80689(8) 0.0184(4) Uani 1 1 d . . . . .
N3B N 1.1992(3) 1.05937(13) 0.73124(10) 0.0228(5) Uani 1 1 d . . . . .
H3BA H 1.141(3) 1.0258(15) 0.7103(11) 0.029(8) Uiso 1 1 d . . . . .
O1B O 1.0315(2) 1.25991(11) 1.05805(7) 0.0356(5) Uani 1 1 d . . . . .
O2B O 1.2766(3) 1.33687(11) 1.05132(8) 0.0383(5) Uani 1 1 d . . . . .
O3B O 1.4151(2) 1.24846(9) 0.76161(7) 0.0240(4) Uani 1 1 d . . . . .
O4B O 1.0430(2) 1.03623(10) 0.81460(7) 0.0265(4) Uani 1 1 d . . . . .
F1B F 1.06128(18) 1.42122(8) 0.96258(6) 0.0344(4) Uani 1 1 d . . . . .
F2B F 1.35275(19) 1.43202(8) 0.94941(6) 0.0343(4) Uani 1 1 d . . . . .
F3B F 1.1509(2) 1.42979(8) 0.87447(6) 0.0369(4) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.385(3) . ?
C1A C6A 1.396(3) . ?
C1A N2A 1.421(3) . ?
C2A C3A 1.383(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.379(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.390(3) . ?
C4A N1A 1.472(3) . ?
C5A C6A 1.387(3) . ?
C5A C7A 1.502(3) . ?
C6A H6A 0.9500 . ?
C7A F2A 1.336(3) . ?
C7A F1A 1.340(2) . ?
C7A F3A 1.348(3) . ?
C8A O3A 1.213(3) . ?
C8A N2A 1.390(3) . ?
C8A C9A 1.514(3) . ?
C9A N3A 1.464(3) . ?
C9A C11A 1.516(3) . ?
C9A C12A 1.531(3) . ?
C10A O4A 1.221(3) . ?
C10A N3A 1.341(3) . ?
C10A N2A 1.428(3) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
N1A O1A 1.229(2) . ?
N1A O2A 1.230(2) . ?
N3A H3AA 0.85(3) . ?
C1B C6B 1.390(3) . ?
C1B C2B 1.391(3) . ?
C1B N2B 1.419(3) . ?
C2B C3B 1.389(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.378(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.389(3) . ?
C4B N1B 1.475(3) . ?
C5B C6B 1.391(3) . ?
C5B C7B 1.507(3) . ?
C6B H6B 0.9500 . ?
C7B F2B 1.336(3) . ?
C7B F3B 1.342(3) . ?
C7B F1B 1.344(3) . ?
C8B O3B 1.212(3) . ?
C8B N2B 1.391(3) . ?
C8B C9B 1.521(3) . ?
C9B N3B 1.460(3) . ?
C9B C12B 1.526(3) . ?
C9B C11B 1.528(3) . ?
C10B O4B 1.213(3) . ?
C10B N3B 1.338(3) . ?
C10B N2B 1.427(3) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
N1B O2B 1.222(3) . ?
N1B O1B 1.228(2) . ?
N3B H3BA 0.81(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
C2A C1A C6A 120.1(2) . . ?
C2A C1A N2A 120.0(2) . . ?
C6A C1A N2A 119.9(2) . . ?
C3A C2A C1A 119.6(2) . . ?
C3A C2A H2A 120.2 . . ?
C1A C2A H2A 120.2 . . ?
C4A C3A C2A 119.9(2) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 121.5(2) . . ?
C3A C4A N1A 116.7(2) . . ?
C5A C4A N1A 121.7(2) . . ?
C6A C5A C4A 118.3(2) . . ?
C6A C5A C7A 117.8(2) . . ?
C4A C5A C7A 123.8(2) . . ?
C5A C6A C1A 120.6(2) . . ?
C5A C6A H6A 119.7 . . ?
C1A C6A H6A 119.7 . . ?
F2A C7A F1A 107.04(19) . . ?
F2A C7A F3A 106.04(19) . . ?
F1A C7A F3A 105.96(18) . . ?
F2A C7A C5A 114.40(19) . . ?
F1A C7A C5A 112.28(19) . . ?
F3A C7A C5A 110.6(2) . . ?
O3A C8A N2A 126.6(2) . . ?
O3A C8A C9A 125.3(2) . . ?
N2A C8A C9A 108.06(19) . . ?
N3A C9A C8A 100.98(18) . . ?
N3A C9A C11A 111.15(19) . . ?
C8A C9A C11A 110.64(19) . . ?
N3A C9A C12A 112.87(19) . . ?
C8A C9A C12A 107.75(19) . . ?
C11A C9A C12A 112.77(19) . . ?
O4A C10A N3A 128.6(2) . . ?
O4A C10A N2A 124.2(2) . . ?
N3A C10A N2A 107.2(2) . . ?
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 . . ?
O1A N1A O2A 124.6(2) . . ?
O1A N1A C4A 117.3(2) . . ?
O2A N1A C4A 118.1(2) . . ?
C8A N2A C1A 125.61(18) . . ?
C8A N2A C10A 109.23(18) . . ?
C1A N2A C10A 124.29(18) . . ?
C10A N3A C9A 113.3(2) . . ?
C10A N3A H3AA 117.0(17) . . ?
C9A N3A H3AA 123.2(17) . . ?
C6B C1B C2B 120.3(2) . . ?
C6B C1B N2B 120.1(2) . . ?
C2B C1B N2B 119.7(2) . . ?
C3B C2B C1B 119.5(2) . . ?
C3B C2B H2B 120.2 . . ?
C1B C2B H2B 120.2 . . ?
C4B C3B C2B 119.6(2) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C3B C4B C5B 121.7(2) . . ?
C3B C4B N1B 117.1(2) . . ?
C5B C4B N1B 121.2(2) . . ?
C4B C5B C6B 118.4(2) . . ?
C4B C5B C7B 122.8(2) . . ?
C6B C5B C7B 118.7(2) . . ?
C1B C6B C5B 120.4(2) . . ?
C1B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
F2B C7B F3B 106.2(2) . . ?
F2B C7B F1B 106.7(2) . . ?
F3B C7B F1B 106.20(19) . . ?
F2B C7B C5B 114.0(2) . . ?
F3B C7B C5B 111.0(2) . . ?
F1B C7B C5B 112.2(2) . . ?
O3B C8B N2B 126.7(2) . . ?
O3B C8B C9B 125.6(2) . . ?
N2B C8B C9B 107.71(19) . . ?
N3B C9B C8B 100.81(18) . . ?
N3B C9B C12B 111.26(19) . . ?
C8B C9B C12B 111.11(19) . . ?
N3B C9B C11B 113.17(19) . . ?
C8B C9B C11B 108.29(19) . . ?
C12B C9B C11B 111.67(19) . . ?
O4B C10B N3B 128.9(2) . . ?
O4B C10B N2B 124.1(2) . . ?
N3B C10B N2B 107.0(2) . . ?
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 . . ?
O2B N1B O1B 125.2(2) . . ?
O2B N1B C4B 117.9(2) . . ?
O1B N1B C4B 116.8(2) . . ?
C8B N2B C1B 125.81(19) . . ?
C8B N2B C10B 109.67(19) . . ?
C1B N2B C10B 123.35(18) . . ?
C10B N3B C9B 113.9(2) . . ?
C10B N3B H3BA 120.0(18) . . ?
C9B N3B H3BA 123.0(18) . . ?

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
C6A C1A C2A C3A 0.1(3) . . . . ?
N2A C1A C2A C3A 179.82(19) . . . . ?
C1A C2A C3A C4A 1.8(3) . . . . ?
C2A C3A C4A C5A -2.5(3) . . . . ?
C2A C3A C4A N1A 175.81(19) . . . . ?
C3A C4A C5A C6A 1.1(3) . . . . ?
N1A C4A C5A C6A -177.1(2) . . . . ?
C3A C4A C5A C7A -174.2(2) . . . . ?
N1A C4A C5A C7A 7.6(3) . . . . ?
C4A C5A C6A C1A 0.8(3) . . . . ?
C7A C5A C6A C1A 176.4(2) . . . . ?
C2A C1A C6A C5A -1.4(3) . . . . ?
N2A C1A C6A C5A 178.82(19) . . . . ?
C6A C5A C7A F2A 101.8(2) . . . . ?
C4A C5A C7A F2A -82.8(3) . . . . ?
C6A C5A C7A F1A -135.9(2) . . . . ?
C4A C5A C7A F1A 39.4(3) . . . . ?
C6A C5A C7A F3A -17.8(3) . . . . ?
C4A C5A C7A F3A 157.6(2) . . . . ?
O3A C8A C9A N3A 177.5(2) . . . . ?
N2A C8A C9A N3A -4.6(2) . . . . ?
O3A C8A C9A C11A 59.8(3) . . . . ?
N2A C8A C9A C11A -122.4(2) . . . . ?
O3A C8A C9A C12A -63.9(3) . . . . ?
N2A C8A C9A C12A 113.9(2) . . . . ?
C3A C4A N1A O1A 40.9(3) . . . . ?
C5A C4A N1A O1A -140.8(2) . . . . ?
C3A C4A N1A O2A -137.7(2) . . . . ?
C5A C4A N1A O2A 40.6(3) . . . . ?
O3A C8A N2A C1A -2.7(4) . . . . ?
C9A C8A N2A C1A 179.55(19) . . . . ?
O3A C8A N2A C10A -172.4(2) . . . . ?
C9A C8A N2A C10A 9.9(2) . . . . ?
C2A C1A N2A C8A 157.2(2) . . . . ?
C6A C1A N2A C8A -23.1(3) . . . . ?
C2A C1A N2A C10A -34.6(3) . . . . ?
C6A C1A N2A C10A 145.1(2) . . . . ?
O4A C10A N2A C8A 168.8(2) . . . . ?
N3A C10A N2A C8A -11.4(2) . . . . ?
O4A C10A N2A C1A -1.1(3) . . . . ?
N3A C10A N2A C1A 178.7(2) . . . . ?
O4A C10A N3A C9A -171.8(2) . . . . ?
N2A C10A N3A C9A 8.5(3) . . . . ?
C8A C9A N3A C10A -2.5(2) . . . . ?
C11A C9A N3A C10A 114.9(2) . . . . ?
C12A C9A N3A C10A -117.2(2) . . . . ?
C6B C1B C2B C3B 1.8(3) . . . . ?
N2B C1B C2B C3B -177.3(2) . . . . ?
C1B C2B C3B C4B -2.6(3) . . . . ?
C2B C3B C4B C5B 1.7(3) . . . . ?
C2B C3B C4B N1B -177.1(2) . . . . ?
C3B C4B C5B C6B 0.0(3) . . . . ?
N1B C4B C5B C6B 178.7(2) . . . . ?
C3B C4B C5B C7B 175.9(2) . . . . ?
N1B C4B C5B C7B -5.3(3) . . . . ?
C2B C1B C6B C5B -0.1(3) . . . . ?
N2B C1B C6B C5B 178.98(19) . . . . ?
C4B C5B C6B C1B -0.8(3) . . . . ?
C7B C5B C6B C1B -176.9(2) . . . . ?
C4B C5B C7B F2B 83.2(3) . . . . ?
C6B C5B C7B F2B -100.9(3) . . . . ?
C4B C5B C7B F3B -156.9(2) . . . . ?
C6B C5B C7B F3B 19.0(3) . . . . ?
C4B C5B C7B F1B -38.2(3) . . . . ?
C6B C5B C7B F1B 137.7(2) . . . . ?
O3B C8B C9B N3B -177.6(2) . . . . ?
N2B C8B C9B N3B 4.0(2) . . . . ?
O3B C8B C9B C12B -59.6(3) . . . . ?
N2B C8B C9B C12B 122.0(2) . . . . ?
O3B C8B C9B C11B 63.3(3) . . . . ?
N2B C8B C9B C11B -115.0(2) . . . . ?
C3B C4B N1B O2B 128.3(2) . . . . ?
C5B C4B N1B O2B -50.5(3) . . . . ?
C3B C4B N1B O1B -50.7(3) . . . . ?
C5B C4B N1B O1B 130.5(2) . . . . ?
O3B C8B N2B C1B 5.0(4) . . . . ?
C9B C8B N2B C1B -176.64(19) . . . . ?
O3B C8B N2B C10B 172.9(2) . . . . ?
C9B C8B N2B C10B -8.7(2) . . . . ?
C6B C1B N2B C8B 25.4(3) . . . . ?
C2B C1B N2B C8B -155.5(2) . . . . ?
C6B C1B N2B C10B -141.0(2) . . . . ?
C2B C1B N2B C10B 38.2(3) . . . . ?
O4B C10B N2B C8B -170.0(2) . . . . ?
N3B C10B N2B C8B 10.2(2) . . . . ?
O4B C10B N2B C1B -1.8(3) . . . . ?
N3B C10B N2B C1B 178.46(19) . . . . ?
O4B C10B N3B C9B 172.6(2) . . . . ?
N2B C10B N3B C9B -7.7(3) . . . . ?
C8B C9B N3B C10B 2.4(3) . . . . ?
C12B C9B N3B C10B -115.5(2) . . . . ?
C11B C9B N3B C10B 117.8(2) . . . . ?

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 H3AA O4B 0.85(3) 2.07(3) 2.911(3) 173(2) . yes
N3B H3BA O4A 0.81(3) 2.17(3) 2.967(3) 168(2) . yes
C12A H12B F3A 0.98 2.35 3.169(3) 140.7 2_656 yes
C11B H11D F3B 0.98 2.40 3.253(3) 145.4 2_746 yes

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB555_0m
_database_code_depnum_ccdc_archive 'CCDC 2252219'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-03-28 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Nilutamide Hydrate (1:0.57)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 N3 O4, 0.285(H2 O)'
_chemical_formula_sum            'C12 H10.57 F3 N3 O4.29'
_chemical_formula_weight         322.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2797(10)
_cell_length_b                   11.1802(11)
_cell_length_c                   13.2382(13)
_cell_angle_alpha                86.915(3)
_cell_angle_beta                 73.762(3)
_cell_angle_gamma                68.854(3)
_cell_volume                     1360.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             659
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?


_diffrn_reflns_number            31137
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0455
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         30.558
_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_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8307
_reflns_number_gt                5999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.3077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8307
_refine_ls_number_parameters     419
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.48580(12) 0.63493(12) 0.34249(9) 0.0141(2) Uani 1 1 d . . . . .
C2A C 0.52621(13) 0.50321(12) 0.32972(10) 0.0169(2) Uani 1 1 d . . . . .
H2A H 0.474501 0.467942 0.298366 0.020 Uiso 1 1 calc R U . . .
C3A C 0.64352(13) 0.42328(12) 0.36342(10) 0.0179(2) Uani 1 1 d . . . . .
H3A H 0.674909 0.332681 0.353377 0.021 Uiso 1 1 calc R U . . .
C4A C 0.71395(13) 0.47710(12) 0.41170(9) 0.0159(2) Uani 1 1 d . . . . .
C5A C 0.67437(13) 0.60936(12) 0.42505(9) 0.0154(2) Uani 1 1 d . . . . .
C6A C 0.55933(13) 0.68836(12) 0.38924(9) 0.0148(2) Uani 1 1 d . . . . .
H6A H 0.530586 0.779019 0.396579 0.018 Uiso 1 1 calc R U . . .
C7A C 0.75289(14) 0.67125(13) 0.47273(11) 0.0216(3) Uani 1 1 d . . . . .
C8A C 0.25685(13) 0.82286(12) 0.37194(10) 0.0155(2) Uani 1 1 d . . . . .
C9A C 0.15626(13) 0.89337(12) 0.30515(10) 0.0182(3) Uani 1 1 d . . . . .
C10A C 0.34784(13) 0.71479(12) 0.20852(10) 0.0166(2) Uani 1 1 d . . . . .
C11A C 0.16514(17) 1.02622(14) 0.28601(13) 0.0308(3) Uani 1 1 d . . . . .
H11A H 0.266634 1.017660 0.254567 0.046 Uiso 1 1 calc R U . . .
H11B H 0.126944 1.076614 0.353140 0.046 Uiso 1 1 calc R U . . .
H11C H 0.107538 1.069813 0.238031 0.046 Uiso 1 1 calc R U . . .
C12A C 0.00189(14) 0.89885(15) 0.35632(11) 0.0262(3) Uani 1 1 d . . . . .
H12A H -0.058485 0.938128 0.309055 0.039 Uiso 1 1 calc R U . . .
H12B H -0.037791 0.950322 0.422984 0.039 Uiso 1 1 calc R U . . .
H12C H 0.002489 0.811642 0.369874 0.039 Uiso 1 1 calc R U . . .
N1A N 0.83164(11) 0.38784(10) 0.45113(9) 0.0188(2) Uani 1 1 d . . . . .
N2A N 0.36678(11) 0.72005(10) 0.30963(8) 0.0138(2) Uani 1 1 d . . . . .
N3A N 0.22398(12) 0.81099(11) 0.20844(8) 0.0207(2) Uani 1 1 d . . . . .
H3AA H 0.186535 0.823581 0.154837 0.025 Uiso 1 1 calc R U . . .
O1A O 0.92793(11) 0.30367(10) 0.38946(8) 0.0303(2) Uani 1 1 d . . . . .
O2A O 0.82346(10) 0.40241(9) 0.54419(7) 0.0212(2) Uani 1 1 d . . . . .
O3A O 0.24525(10) 0.85038(9) 0.46159(7) 0.0218(2) Uani 1 1 d . . . . .
O4A O 0.43211(10) 0.63625(10) 0.13788(7) 0.0240(2) Uani 1 1 d . . . . .
F1A F 0.89616(9) 0.60646(8) 0.44590(7) 0.0299(2) Uani 1 1 d . . . . .
F2A F 0.70565(10) 0.68165(9) 0.57793(7) 0.0319(2) Uani 1 1 d . . . . .
F3A F 0.73327(10) 0.79041(8) 0.44034(8) 0.0338(2) Uani 1 1 d . . . . .
C1B C -0.14005(13) 0.68972(11) 0.14608(9) 0.0139(2) Uani 1 1 d . . . . .
C2B C -0.22115(13) 0.62568(12) 0.12081(9) 0.0165(2) Uani 1 1 d . . . . .
H2B H -0.309882 0.672644 0.104862 0.020 Uiso 1 1 calc R U . . .
C3B C -0.17156(14) 0.49310(12) 0.11909(9) 0.0175(2) Uani 1 1 d . . . . .
H3B H -0.227463 0.448432 0.103913 0.021 Uiso 1 1 calc R U . . .
C4B C -0.04047(14) 0.42583(12) 0.13953(9) 0.0163(2) Uani 1 1 d . . . . .
C5B C 0.04295(13) 0.48802(12) 0.16541(9) 0.0153(2) Uani 1 1 d . . . . .
C6B C -0.01054(13) 0.62160(12) 0.17055(9) 0.0147(2) Uani 1 1 d . . . . .
H6B H 0.041550 0.666644 0.190880 0.018 Uiso 1 1 calc R U . . .
C7B C 0.18637(14) 0.41994(12) 0.18932(10) 0.0187(3) Uani 1 1 d . . . . .
C8B C -0.09525(13) 0.89436(12) 0.09944(9) 0.0143(2) Uani 1 1 d . . . . .
C9B C -0.33334(13) 1.04329(12) 0.14279(10) 0.0178(2) Uani 1 1 d . . . . .
C10B C -0.33295(13) 0.90910(12) 0.17067(10) 0.0165(2) Uani 1 1 d . . . . .
C11B C -0.40409(16) 1.13406(14) 0.24038(12) 0.0284(3) Uani 1 1 d . . . . .
H11D H -0.352911 1.099869 0.293956 0.043 Uiso 1 1 calc R U . . .
H11E H -0.505997 1.142216 0.268247 0.043 Uiso 1 1 calc R U . . .
H11F H -0.398971 1.218620 0.221841 0.043 Uiso 1 1 calc R U . . .
C12B C -0.41086(15) 1.09128(14) 0.05710(12) 0.0249(3) Uani 1 1 d . . . . .
H12D H -0.407968 1.176199 0.037267 0.037 Uiso 1 1 calc R U . . .
H12E H -0.512159 1.097247 0.083899 0.037 Uiso 1 1 calc R U . . .
H12F H -0.362117 1.031128 -0.004747 0.037 Uiso 1 1 calc R U . . .
N1B N 0.00735(13) 0.28499(10) 0.12891(8) 0.0186(2) Uani 1 1 d . . . . .
N2B N -0.18839(11) 0.82618(10) 0.14552(8) 0.0140(2) Uani 1 1 d . . . . .
N3B N -0.17802(11) 1.01756(10) 0.10257(8) 0.0172(2) Uani 1 1 d . . . . .
H3BA H -0.142247 1.078313 0.082169 0.021 Uiso 1 1 calc R U . . .
O1B O -0.08536(11) 0.23705(9) 0.16207(7) 0.0248(2) Uani 1 1 d . . . . .
O2B O 0.13571(11) 0.22453(9) 0.08390(7) 0.0230(2) Uani 1 1 d . . . . .
O3B O 0.03722(9) 0.84380(8) 0.06466(7) 0.01697(18) Uani 1 1 d . . . . .
O4B O -0.43819(10) 0.87998(9) 0.20758(8) 0.0243(2) Uani 1 1 d . . . . .
F1B F 0.18958(9) 0.31583(7) 0.24449(6) 0.02428(18) Uani 1 1 d . . . . .
F2B F 0.29721(8) 0.38343(8) 0.10169(6) 0.02725(19) Uani 1 1 d . . . . .
F3B F 0.21508(9) 0.49765(7) 0.24676(7) 0.02582(19) Uani 1 1 d . . . . .
O1W O 0.38804(19) 0.61220(17) -0.06023(14) 0.0237(6) Uani 0.570(4) 1 d D . P .
.
H1W H 0.453(3) 0.5344(18) -0.086(3) 0.057(11) Uiso 0.570(4) 1 d D . P . .
H2W H 0.394(4) 0.622(4) 0.0053(14) 0.063(12) Uiso 0.570(4) 1 d D . P . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.3841(17) . ?
C1A C6A 1.3923(16) . ?
C1A N2A 1.4160(14) . ?
C2A C3A 1.3901(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3818(17) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3918(18) . ?
C4A N1A 1.4690(15) . ?
C5A C6A 1.3850(16) . ?
C5A C7A 1.5045(17) . ?
C6A H6A 0.9500 . ?
C7A F1A 1.3362(15) . ?
C7A F2A 1.3370(16) . ?
C7A F3A 1.3388(16) . ?
C8A O3A 1.2047(14) . ?
C8A N2A 1.3864(15) . ?
C8A C9A 1.5233(16) . ?
C9A N3A 1.4622(17) . ?
C9A C12A 1.5212(19) . ?
C9A C11A 1.524(2) . ?
C10A O4A 1.2176(15) . ?
C10A N3A 1.3381(16) . ?
C10A N2A 1.4126(15) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
N1A O1A 1.2209(14) . ?
N1A O2A 1.2268(14) . ?
N3A H3AA 0.8800 . ?
C1B C2B 1.3899(16) . ?
C1B C6B 1.3930(16) . ?
C1B N2B 1.4243(15) . ?
C2B C3B 1.3818(17) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3804(17) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3987(17) . ?
C4B N1B 1.4723(16) . ?
C5B C6B 1.3910(17) . ?
C5B C7B 1.5095(17) . ?
C6B H6B 0.9500 . ?
C7B F1B 1.3356(15) . ?
C7B F2B 1.3367(15) . ?
C7B F3B 1.3423(14) . ?
C8B O3B 1.2280(14) . ?
C8B N3B 1.3280(16) . ?
C8B N2B 1.4211(16) . ?
C9B N3B 1.4579(16) . ?
C9B C11B 1.5202(19) . ?
C9B C10B 1.5244(18) . ?
C9B C12B 1.5301(18) . ?
C10B O4B 1.2069(15) . ?
C10B N2B 1.3933(15) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
N1B O1B 1.2237(14) . ?
N1B O2B 1.2301(14) . ?
N3B H3BA 0.8800 . ?
O1W H1W 0.897(10) . ?
O1W H2W 0.900(10) . ?

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 121.29(11) . . ?
C2A C1A N2A 121.03(10) . . ?
C6A C1A N2A 117.67(11) . . ?
C1A C2A C3A 119.06(11) . . ?
C1A C2A H2A 120.5 . . ?
C3A C2A H2A 120.5 . . ?
C4A C3A C2A 119.25(11) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C3A C4A C5A 122.23(11) . . ?
C3A C4A N1A 116.81(11) . . ?
C5A C4A N1A 120.94(10) . . ?
C6A C5A C4A 118.14(11) . . ?
C6A C5A C7A 118.18(11) . . ?
C4A C5A C7A 123.65(10) . . ?
C5A C6A C1A 120.00(11) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
F1A C7A F2A 107.60(10) . . ?
F1A C7A F3A 106.72(11) . . ?
F2A C7A F3A 106.53(11) . . ?
F1A C7A C5A 112.28(11) . . ?
F2A C7A C5A 112.34(11) . . ?
F3A C7A C5A 111.04(10) . . ?
O3A C8A N2A 125.80(11) . . ?
O3A C8A C9A 127.22(11) . . ?
N2A C8A C9A 106.97(10) . . ?
N3A C9A C12A 111.73(11) . . ?
N3A C9A C8A 100.74(10) . . ?
C12A C9A C8A 111.21(11) . . ?
N3A C9A C11A 111.29(11) . . ?
C12A C9A C11A 112.59(11) . . ?
C8A C9A C11A 108.63(11) . . ?
O4A C10A N3A 129.14(11) . . ?
O4A C10A N2A 124.36(11) . . ?
N3A C10A N2A 106.49(10) . . ?
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 . . ?
O1A N1A O2A 125.27(11) . . ?
O1A N1A C4A 117.54(10) . . ?
O2A N1A C4A 117.18(10) . . ?
C8A N2A C10A 111.44(10) . . ?
C8A N2A C1A 123.83(10) . . ?
C10A N2A C1A 124.68(10) . . ?
C10A N3A C9A 114.16(10) . . ?
C10A N3A H3AA 122.9 . . ?
C9A N3A H3AA 122.9 . . ?
C2B C1B C6B 120.64(11) . . ?
C2B C1B N2B 119.84(10) . . ?
C6B C1B N2B 119.51(10) . . ?
C3B C2B C1B 119.41(11) . . ?
C3B C2B H2B 120.3 . . ?
C1B C2B H2B 120.3 . . ?
C4B C3B C2B 119.73(11) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 121.92(11) . . ?
C3B C4B N1B 115.56(11) . . ?
C5B C4B N1B 122.49(11) . . ?
C6B C5B C4B 117.82(11) . . ?
C6B C5B C7B 117.78(11) . . ?
C4B C5B C7B 124.40(11) . . ?
C5B C6B C1B 120.39(11) . . ?
C5B C6B H6B 119.8 . . ?
C1B C6B H6B 119.8 . . ?
F1B C7B F2B 107.58(10) . . ?
F1B C7B F3B 106.39(10) . . ?
F2B C7B F3B 106.55(10) . . ?
F1B C7B C5B 113.13(11) . . ?
F2B C7B C5B 112.02(10) . . ?
F3B C7B C5B 110.78(10) . . ?
O3B C8B N3B 128.55(12) . . ?
O3B C8B N2B 124.05(11) . . ?
N3B C8B N2B 107.41(10) . . ?
N3B C9B C11B 112.41(11) . . ?
N3B C9B C10B 100.93(9) . . ?
C11B C9B C10B 110.49(11) . . ?
N3B C9B C12B 111.48(11) . . ?
C11B C9B C12B 111.59(11) . . ?
C10B C9B C12B 109.43(10) . . ?
O4B C10B N2B 126.32(12) . . ?
O4B C10B C9B 126.43(11) . . ?
N2B C10B C9B 107.25(10) . . ?
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 . . ?
O1B N1B O2B 124.73(11) . . ?
O1B N1B C4B 117.24(11) . . ?
O2B N1B C4B 117.97(11) . . ?
C10B N2B C8B 110.14(10) . . ?
C10B N2B C1B 125.42(10) . . ?
C8B N2B C1B 123.41(10) . . ?
C8B N3B C9B 114.08(10) . . ?
C8B N3B H3BA 123.0 . . ?
C9B N3B H3BA 123.0 . . ?
H1W O1W H2W 106(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
C6A C1A C2A C3A -0.67(19) . . . . ?
N2A C1A C2A C3A -179.82(11) . . . . ?
C1A C2A C3A C4A 1.98(19) . . . . ?
C2A C3A C4A C5A -2.02(19) . . . . ?
C2A C3A C4A N1A 176.56(11) . . . . ?
C3A C4A C5A C6A 0.66(19) . . . . ?
N1A C4A C5A C6A -177.86(11) . . . . ?
C3A C4A C5A C7A -177.10(12) . . . . ?
N1A C4A C5A C7A 4.38(19) . . . . ?
C4A C5A C6A C1A 0.70(18) . . . . ?
C7A C5A C6A C1A 178.59(11) . . . . ?
C2A C1A C6A C5A -0.70(19) . . . . ?
N2A C1A C6A C5A 178.48(11) . . . . ?
C6A C5A C7A F1A -141.40(12) . . . . ?
C4A C5A C7A F1A 36.36(17) . . . . ?
C6A C5A C7A F2A 97.16(14) . . . . ?
C4A C5A C7A F2A -85.08(15) . . . . ?
C6A C5A C7A F3A -22.02(17) . . . . ?
C4A C5A C7A F3A 155.74(12) . . . . ?
O3A C8A C9A N3A -177.57(13) . . . . ?
N2A C8A C9A N3A 2.91(13) . . . . ?
O3A C8A C9A C12A -59.02(18) . . . . ?
N2A C8A C9A C12A 121.46(12) . . . . ?
O3A C8A C9A C11A 65.43(17) . . . . ?
N2A C8A C9A C11A -114.09(12) . . . . ?
C3A C4A N1A O1A 53.12(16) . . . . ?
C5A C4A N1A O1A -128.29(13) . . . . ?
C3A C4A N1A O2A -125.39(13) . . . . ?
C5A C4A N1A O2A 53.21(16) . . . . ?
O3A C8A N2A C10A 179.79(12) . . . . ?
C9A C8A N2A C10A -0.68(14) . . . . ?
O3A C8A N2A C1A -2.7(2) . . . . ?
C9A C8A N2A C1A 176.83(11) . . . . ?
O4A C10A N2A C8A 177.41(12) . . . . ?
N3A C10A N2A C8A -2.13(14) . . . . ?
O4A C10A N2A C1A -0.1(2) . . . . ?
N3A C10A N2A C1A -179.61(11) . . . . ?
C2A C1A N2A C8A 131.47(13) . . . . ?
C6A C1A N2A C8A -47.71(16) . . . . ?
C2A C1A N2A C10A -51.35(17) . . . . ?
C6A C1A N2A C10A 129.47(12) . . . . ?
O4A C10A N3A C9A -175.19(13) . . . . ?
N2A C10A N3A C9A 4.32(15) . . . . ?
C12A C9A N3A C10A -122.70(12) . . . . ?
C8A C9A N3A C10A -4.53(14) . . . . ?
C11A C9A N3A C10A 110.49(13) . . . . ?
C6B C1B C2B C3B -0.62(18) . . . . ?
N2B C1B C2B C3B 178.44(11) . . . . ?
C1B C2B C3B C4B -1.81(19) . . . . ?
C2B C3B C4B C5B 2.01(19) . . . . ?
C2B C3B C4B N1B -176.11(11) . . . . ?
C3B C4B C5B C6B 0.25(18) . . . . ?
N1B C4B C5B C6B 178.24(11) . . . . ?
C3B C4B C5B C7B 179.54(12) . . . . ?
N1B C4B C5B C7B -2.47(19) . . . . ?
C4B C5B C6B C1B -2.69(18) . . . . ?
C7B C5B C6B C1B 177.97(11) . . . . ?
C2B C1B C6B C5B 2.93(18) . . . . ?
N2B C1B C6B C5B -176.14(11) . . . . ?
C6B C5B C7B F1B 141.03(11) . . . . ?
C4B C5B C7B F1B -38.26(17) . . . . ?
C6B C5B C7B F2B -97.16(13) . . . . ?
C4B C5B C7B F2B 83.55(15) . . . . ?
C6B C5B C7B F3B 21.67(16) . . . . ?
C4B C5B C7B F3B -157.62(12) . . . . ?
N3B C9B C10B O4B -179.96(12) . . . . ?
C11B C9B C10B O4B 60.92(17) . . . . ?
C12B C9B C10B O4B -62.34(17) . . . . ?
N3B C9B C10B N2B -0.02(12) . . . . ?
C11B C9B C10B N2B -119.14(11) . . . . ?
C12B C9B C10B N2B 117.60(11) . . . . ?
C3B C4B N1B O1B -40.49(15) . . . . ?
C5B C4B N1B O1B 141.40(12) . . . . ?
C3B C4B N1B O2B 136.71(12) . . . . ?
C5B C4B N1B O2B -41.40(16) . . . . ?
O4B C10B N2B C8B 177.43(12) . . . . ?
C9B C10B N2B C8B -2.51(13) . . . . ?
O4B C10B N2B C1B 8.8(2) . . . . ?
C9B C10B N2B C1B -171.17(10) . . . . ?
O3B C8B N2B C10B -176.02(11) . . . . ?
N3B C8B N2B C10B 4.27(13) . . . . ?
O3B C8B N2B C1B -7.09(17) . . . . ?
N3B C8B N2B C1B 173.20(10) . . . . ?
C2B C1B N2B C10B 32.14(17) . . . . ?
C6B C1B N2B C10B -148.78(12) . . . . ?
C2B C1B N2B C8B -135.08(12) . . . . ?
C6B C1B N2B C8B 44.00(16) . . . . ?
O3B C8B N3B C9B 175.88(11) . . . . ?
N2B C8B N3B C9B -4.42(13) . . . . ?
C11B C9B N3B C8B 120.53(12) . . . . ?
C10B C9B N3B C8B 2.79(13) . . . . ?
C12B C9B N3B C8B -113.32(12) . . . . ?

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 H3AA O3B 0.88 2.14 2.9839(13) 160.6 . yes
N3B H3BA O3B 0.88 2.24 2.9759(14) 140.8 2_575 yes
N3B H3BA O1B 0.88 2.43 3.1406(14) 138.1 1_565 yes
O1W H1W O4A 0.897(10) 1.889(11) 2.780(2) 172(3) 2_665 yes
C11A H11B O1A 0.98 2.59 3.2520(18) 125.2 1_465 yes
C11A H11C O1B 0.98 2.58 3.5280(17) 161.7 1_565 yes
C3B H3B O1W 0.95 2.21 3.147(2) 167.0 2_565 yes
C12B H12D O1W 0.98 2.49 3.410(2) 156.6 2_575 yes

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KA997_0m
_database_code_depnum_ccdc_archive 'CCDC 2252220'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-03-28 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Nilutamide-Adenine cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 N3 O4, C5 H5 N5'
_chemical_formula_sum            'C17 H15 F3 N8 O4'
_chemical_formula_weight         452.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   7.3886(5)
_cell_length_b                   12.2118(8)
_cell_length_c                   20.8355(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.845(3)
_cell_angle_gamma                90
_cell_volume                     1857.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?


_diffrn_reflns_number            16255
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4256
_reflns_number_gt                3867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+6.9580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     344
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.1496(4) 0.3784(2) 0.38887(13) 0.0126(5) Uani 1 1 d . . . . .
C2 C 0.0622(4) 0.3581(2) 0.32582(14) 0.0160(6) Uani 1 1 d . . . . .
H2 H 0.012687 0.417124 0.299003 0.019 Uiso 1 1 calc R U . . .
C3 C 0.0476(4) 0.2516(3) 0.30223(14) 0.0189(6) Uani 1 1 d . . . . .
H3 H -0.006718 0.237620 0.258650 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1124(4) 0.1667(2) 0.34250(15) 0.0159(6) Uani 1 1 d . . . . .
C5 C 0.1958(4) 0.1846(2) 0.40590(14) 0.0165(6) Uani 1 1 d . . . . .
C6 C 0.2187(4) 0.2913(2) 0.42858(14) 0.0159(6) Uani 1 1 d . . . . .
H6 H 0.281373 0.305115 0.471133 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2643(5) 0.0921(3) 0.45063(16) 0.0246(7) Uani 1 1 d . . . . .
C8 C 0.2055(4) 0.5175(2) 0.47997(13) 0.0147(6) Uani 1 1 d . . . . .
C9 C 0.1763(4) 0.6802(2) 0.42033(13) 0.0152(6) Uani 1 1 d . . . . .
C10 C 0.1555(4) 0.5820(2) 0.37489(14) 0.0158(6) Uani 1 1 d . . . . .
C11 C 0.0006(5) 0.7470(3) 0.41163(16) 0.0219(6) Uani 1 1 d . . . . .
H11A H -0.023816 0.775531 0.367179 0.033 Uiso 1 1 calc R U . . .
H11B H 0.013911 0.808186 0.442437 0.033 Uiso 1 1 calc R U . . .
H11C H -0.101480 0.700368 0.419674 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3385(5) 0.7492(3) 0.40817(18) 0.0253(7) Uani 1 1 d . . . . .
H12A H 0.316651 0.777241 0.363576 0.038 Uiso 1 1 calc R U . . .
H12B H 0.449591 0.704218 0.414388 0.038 Uiso 1 1 calc R U . . .
H12C H 0.353817 0.810781 0.438701 0.038 Uiso 1 1 calc R U . . .
N1 N 0.0923(4) 0.0544(2) 0.31643(13) 0.0213(6) Uani 1 1 d . . . . .
N2 N 0.1680(3) 0.48752(19) 0.41288(11) 0.0124(5) Uani 1 1 d . . . . .
N3 N 0.2106(4) 0.6261(2) 0.48353(12) 0.0170(5) Uani 1 1 d . . . . .
H1N H 0.244(5) 0.661(3) 0.518(2) 0.025(10) Uiso 1 1 d . . . . .
O2 O -0.0237(4) -0.0034(2) 0.33239(13) 0.0357(7) Uani 1 1 d . . . . .
O3 O 0.2265(3) 0.45260(17) 0.52509(10) 0.0200(5) Uani 1 1 d . . . . .
O4 O 0.1327(4) 0.58717(19) 0.31629(10) 0.0253(5) Uani 1 1 d . . . . .
O1 O 0.1887(5) 0.0324(4) 0.2730(2) 0.0248(10) Uani 0.767(12) 1 d . U P A 1
F1 F 0.3542(6) 0.0187(3) 0.4197(2) 0.0312(9) Uani 0.767(12) 1 d . . P A 1
F2 F 0.3682(12) 0.1264(6) 0.5024(4) 0.055(2) Uani 0.767(12) 1 d . U P A 1
F3 F 0.1233(6) 0.0387(4) 0.4700(2) 0.0354(10) Uani 0.767(12) 1 d . U P A 1
O1D O 0.2158(19) 0.0004(12) 0.3075(11) 0.035(4) Uani 0.233(12) 1 d . U P A 2
F1D F 0.436(2) 0.0514(13) 0.4439(8) 0.038(5) Uani 0.233(12) 1 d . . P A 2
F2D F 0.306(3) 0.122(2) 0.5170(10) 0.033(4) Uani 0.233(12) 1 d . U P A 2
F3D F 0.163(2) 0.0035(11) 0.4520(7) 0.029(3) Uani 0.233(12) 1 d . U P A 2
C13 C 0.4162(4) 0.6831(2) 0.66968(13) 0.0125(5) Uani 1 1 d . . . . .
C14 C 0.4581(4) 0.5762(2) 0.69240(13) 0.0122(5) Uani 1 1 d . . . . .
C15 C 0.5916(4) 0.6564(2) 0.78981(13) 0.0140(5) Uani 1 1 d . . . . .
H15 H 0.656498 0.644376 0.832234 0.017 Uiso 1 1 calc R U . . .
C16 C 0.4644(4) 0.7681(2) 0.71289(13) 0.0132(5) Uani 1 1 d . . . . .
C17 C 0.3179(4) 0.8300(2) 0.62129(14) 0.0167(6) Uani 1 1 d . . . . .
H17 H 0.261526 0.880027 0.589455 0.020 Uiso 1 1 calc R U . . .
N4 N 0.4131(4) 0.4861(2) 0.65751(12) 0.0176(5) Uani 1 1 d . . . . .
H2N H 0.429(6) 0.425(4) 0.678(2) 0.030(11) Uiso 1 1 d . . . . .
H3N H 0.342(6) 0.493(4) 0.619(2) 0.031(11) Uiso 1 1 d . . . . .
N5 N 0.5496(3) 0.5659(2) 0.75398(11) 0.0134(5) Uani 1 1 d . . . . .
N6 N 0.5549(3) 0.7601(2) 0.77413(11) 0.0150(5) Uani 1 1 d . . . . .
N7 N 0.4001(4) 0.8619(2) 0.68137(12) 0.0160(5) Uani 1 1 d . . . . .
H4N H 0.402(6) 0.938(4) 0.699(2) 0.045(13) Uiso 1 1 d . . . . .
N8 N 0.3232(3) 0.7236(2) 0.61112(11) 0.0149(5) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.394(4) . ?
C1 C6 1.395(4) . ?
C1 N2 1.423(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 N1 1.474(4) . ?
C5 C6 1.389(4) . ?
C5 C7 1.501(4) . ?
C6 H6 0.9500 . ?
C7 F2 1.294(8) . ?
C7 F3D 1.317(12) . ?
C7 F1 1.339(5) . ?
C7 F3 1.343(6) . ?
C7 F1D 1.388(11) . ?
C7 F2D 1.42(2) . ?
C8 O3 1.221(4) . ?
C8 N3 1.328(4) . ?
C8 N2 1.430(3) . ?
C9 N3 1.460(4) . ?
C9 C12 1.518(4) . ?
C9 C11 1.520(4) . ?
C9 C10 1.521(4) . ?
C10 O4 1.208(4) . ?
C10 N2 1.394(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 O1D 1.163(12) . ?
N1 O2 1.196(4) . ?
N1 O1 1.264(5) . ?
N3 H1N 0.85(4) . ?
C13 C16 1.384(4) . ?
C13 N8 1.396(3) . ?
C13 C14 1.407(4) . ?
C14 N4 1.332(4) . ?
C14 N5 1.361(3) . ?
C15 N6 1.326(4) . ?
C15 N5 1.342(4) . ?
C15 H15 0.9500 . ?
C16 N6 1.350(4) . ?
C16 N7 1.369(4) . ?
C17 N8 1.317(4) . ?
C17 N7 1.362(4) . ?
C17 H17 0.9500 . ?
N4 H2N 0.86(4) . ?
N4 H3N 0.90(4) . ?
N7 H4N 1.00(5) . ?

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
C2 C1 C6 119.9(3) . . ?
C2 C1 N2 120.2(2) . . ?
C6 C1 N2 119.9(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 N1 118.1(3) . . ?
C5 C4 N1 120.2(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 C7 122.1(3) . . ?
C6 C5 C7 118.9(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
F2 C7 F1 110.1(4) . . ?
F2 C7 F3 107.1(5) . . ?
F1 C7 F3 106.6(3) . . ?
F3D C7 F1D 103.7(8) . . ?
F3D C7 F2D 103.4(11) . . ?
F1D C7 F2D 97.2(12) . . ?
F2 C7 C5 112.0(4) . . ?
F3D C7 C5 119.5(6) . . ?
F1 C7 C5 110.4(3) . . ?
F3 C7 C5 110.4(3) . . ?
F1D C7 C5 115.6(5) . . ?
F2D C7 C5 114.4(11) . . ?
O3 C8 N3 127.3(3) . . ?
O3 C8 N2 124.6(3) . . ?
N3 C8 N2 108.1(2) . . ?
N3 C9 C12 111.7(3) . . ?
N3 C9 C11 112.2(2) . . ?
C12 C9 C11 111.3(3) . . ?
N3 C9 C10 101.0(2) . . ?
C12 C9 C10 109.9(3) . . ?
C11 C9 C10 110.2(2) . . ?
O4 C10 N2 127.1(3) . . ?
O4 C10 C9 125.0(3) . . ?
N2 C10 C9 107.9(2) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1D N1 O2 108.9(8) . . ?
O2 N1 O1 125.6(3) . . ?
O1D N1 C4 123.3(7) . . ?
O2 N1 C4 118.8(3) . . ?
O1 N1 C4 115.2(3) . . ?
C10 N2 C1 125.6(2) . . ?
C10 N2 C8 109.2(2) . . ?
C1 N2 C8 125.3(2) . . ?
C8 N3 C9 113.7(2) . . ?
C8 N3 H1N 124(3) . . ?
C9 N3 H1N 122(3) . . ?
C16 C13 N8 110.2(2) . . ?
C16 C13 C14 117.1(2) . . ?
N8 C13 C14 132.6(3) . . ?
N4 C14 N5 119.0(3) . . ?
N4 C14 C13 124.0(3) . . ?
N5 C14 C13 117.0(2) . . ?
N6 C15 N5 128.9(3) . . ?
N6 C15 H15 115.5 . . ?
N5 C15 H15 115.5 . . ?
N6 C16 N7 126.8(3) . . ?
N6 C16 C13 127.0(3) . . ?
N7 C16 C13 106.3(2) . . ?
N8 C17 N7 114.2(3) . . ?
N8 C17 H17 122.9 . . ?
N7 C17 H17 122.9 . . ?
C14 N4 H2N 116(3) . . ?
C14 N4 H3N 119(3) . . ?
H2N N4 H3N 123(4) . . ?
C15 N5 C14 119.2(2) . . ?
C15 N6 C16 110.8(2) . . ?
C17 N7 C16 105.9(2) . . ?
C17 N7 H4N 126(3) . . ?
C16 N7 H4N 128(3) . . ?
C17 N8 C13 103.4(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
C6 C1 C2 C3 -1.4(4) . . . . ?
N2 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 2.9(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C2 C3 C4 N1 179.0(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
N1 C4 C5 C6 177.8(3) . . . . ?
C3 C4 C5 C7 179.0(3) . . . . ?
N1 C4 C5 C7 -1.4(5) . . . . ?
C4 C5 C6 C1 3.4(5) . . . . ?
C7 C5 C6 C1 -177.4(3) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
N2 C1 C6 C5 178.0(3) . . . . ?
C4 C5 C7 F2 167.3(5) . . . . ?
C6 C5 C7 F2 -11.9(6) . . . . ?
C4 C5 C7 F3D -42.8(11) . . . . ?
C6 C5 C7 F3D 137.9(11) . . . . ?
C4 C5 C7 F1 44.2(5) . . . . ?
C6 C5 C7 F1 -135.0(4) . . . . ?
C4 C5 C7 F3 -73.4(5) . . . . ?
C6 C5 C7 F3 107.4(4) . . . . ?
C4 C5 C7 F1D 82.2(11) . . . . ?
C6 C5 C7 F1D -97.0(11) . . . . ?
C4 C5 C7 F2D -166.1(10) . . . . ?
C6 C5 C7 F2D 14.6(11) . . . . ?
N3 C9 C10 O4 -176.7(3) . . . . ?
C12 C9 C10 O4 -58.6(4) . . . . ?
C11 C9 C10 O4 64.5(4) . . . . ?
N3 C9 C10 N2 3.1(3) . . . . ?
C12 C9 C10 N2 121.3(3) . . . . ?
C11 C9 C10 N2 -115.6(3) . . . . ?
C3 C4 N1 O1D 112.4(15) . . . . ?
C5 C4 N1 O1D -67.3(15) . . . . ?
C3 C4 N1 O2 -104.3(4) . . . . ?
C5 C4 N1 O2 76.1(4) . . . . ?
C3 C4 N1 O1 68.2(4) . . . . ?
C5 C4 N1 O1 -111.4(4) . . . . ?
O4 C10 N2 C1 -2.3(5) . . . . ?
C9 C10 N2 C1 177.9(3) . . . . ?
O4 C10 N2 C8 176.7(3) . . . . ?
C9 C10 N2 C8 -3.1(3) . . . . ?
C2 C1 N2 C10 -19.9(4) . . . . ?
C6 C1 N2 C10 160.3(3) . . . . ?
C2 C1 N2 C8 161.2(3) . . . . ?
C6 C1 N2 C8 -18.6(4) . . . . ?
O3 C8 N2 C10 -179.0(3) . . . . ?
N3 C8 N2 C10 1.7(3) . . . . ?
O3 C8 N2 C1 0.1(5) . . . . ?
N3 C8 N2 C1 -179.2(3) . . . . ?
O3 C8 N3 C9 -178.8(3) . . . . ?
N2 C8 N3 C9 0.5(4) . . . . ?
C12 C9 N3 C8 -119.1(3) . . . . ?
C11 C9 N3 C8 115.2(3) . . . . ?
C10 C9 N3 C8 -2.2(3) . . . . ?
C16 C13 C14 N4 176.9(3) . . . . ?
N8 C13 C14 N4 1.1(5) . . . . ?
C16 C13 C14 N5 -2.9(4) . . . . ?
N8 C13 C14 N5 -178.6(3) . . . . ?
N8 C13 C16 N6 179.8(3) . . . . ?
C14 C13 C16 N6 3.1(4) . . . . ?
N8 C13 C16 N7 0.4(3) . . . . ?
C14 C13 C16 N7 -176.3(3) . . . . ?
N6 C15 N5 C14 0.6(5) . . . . ?
N4 C14 N5 C15 -178.5(3) . . . . ?
C13 C14 N5 C15 1.3(4) . . . . ?
N5 C15 N6 C16 -0.6(4) . . . . ?
N7 C16 N6 C15 177.9(3) . . . . ?
C13 C16 N6 C15 -1.3(4) . . . . ?
N8 C17 N7 C16 0.0(4) . . . . ?
N6 C16 N7 C17 -179.6(3) . . . . ?
C13 C16 N7 C17 -0.3(3) . . . . ?
N7 C17 N8 C13 0.2(4) . . . . ?
C16 C13 N8 C17 -0.4(3) . . . . ?
C14 C13 N8 C17 175.6(3) . . . . ?

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
N3 H1N N8 0.85(4) 2.08(4) 2.915(3) 171(4) . yes
N4 H2N N6 0.86(4) 2.24(5) 3.099(4) 175(4) 2_646 yes
N4 H3N O3 0.90(4) 2.06(4) 2.917(3) 158(4) . yes
N7 H4N N5 1.00(5) 1.85(5) 2.829(3) 167(4) 2_656 yes
C2 H2 O1^a 0.95 2.40 3.321(4) 163.4 2 yes
C3 H3 O4 0.95 2.50 3.300(4) 142.4 2_545 yes
C11 H11C O3 0.98 2.45 3.343(4) 151.6 3_566 yes
C12 H12C F2^a 0.98 2.35 3.039(8) 126.4 3_666 yes

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.088

