#------------------------------------------------------------------------------
#$Date: 2022-04-01 01:33:08 +0300 (Fri, 01 Apr 2022) $
#$Revision: 274178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244690.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_7244690
loop_
_publ_author_name
'Prashanth, Jupally'
'Arikatla, Sivalakshmi Devi'
'Surov, Artem'
'Voronin, Alexander P.'
'Andrei, Churakov'
'Perlovich, German L.'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Understanding the thermal stability of apalutamide crystalline solvates
 through crystal structure analyses and computational studies
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00216G
_journal_year                    2022
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C2 H6 O'
_chemical_formula_sum            'C44 H36 F8 N10 O5 S2'
_chemical_formula_weight         1000.95
_chemical_name_common            Apalutamide-Ethanol-2:1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.568(10)
_cell_length_b                   37.54(2)
_cell_length_c                   7.364(5)
_cell_measurement_reflns_used    5718
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.46
_cell_volume                     4580(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0850
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            27853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.494
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4726
_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    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         8064
_refine_ls_number_restraints     562
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1186P)²+0.5342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1782
_refine_ls_wR_factor_ref         0.2143
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5112
_reflns_number_total             8064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00216g2.cif
_cod_data_source_block           KB101_0m_APA-EtOH-2-1
_cod_database_code               7244690
_shelx_shelxl_version_number     2018/3
_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   0.948
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
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 0.6106(4) 0.26475(17) 0.5465(10) 0.0370(17) Uani 1 1 d . . . . .
C2A C 0.5865(5) 0.24902(17) 0.3840(11) 0.0404(19) Uani 1 1 d . . . . .
H2A H 0.560611 0.262025 0.293733 0.048 Uiso 1 1 calc R U . . .
C3A C 0.6029(5) 0.21319(18) 0.3635(10) 0.0397(19) Uani 1 1 d . . . . .
C4A C 0.6408(5) 0.19494(17) 0.5017(11) 0.042(2) Uani 1 1 d . . . . .
C5A C 0.6459(5) 0.24467(17) 0.6801(12) 0.049(2) Uani 1 1 d . . . . .
H5A H 0.659521 0.255531 0.789402 0.058 Uiso 1 1 calc R U . . .
C6A C 0.6199(4) 0.32931(17) 0.4618(10) 0.0367(17) Uani 1 1 d . . . . .
C7A C 0.5458(5) 0.35458(17) 0.7032(10) 0.0400(18) Uani 1 1 d . . . . .
C8A C 0.5516(5) 0.31459(17) 0.7236(11) 0.0426(19) Uani 1 1 d . . . . .
C9A C 0.5746(6) 0.1949(2) 0.1896(13) 0.055(2) Uani 1 1 d D . . . .
C10A C 0.6622(6) 0.1578(2) 0.4879(14) 0.062(3) Uani 1 1 d . . . . .
C11A C 0.6085(5) 0.39387(17) 0.4635(10) 0.0373(18) Uani 1 1 d . . . . .
C12A C 0.6813(5) 0.40904(18) 0.4937(9) 0.0420(19) Uani 1 1 d . . . . .
H12A H 0.721457 0.396972 0.556863 0.050 Uiso 1 1 calc R U . . .
C13A C 0.6942(5) 0.44312(18) 0.4277(11) 0.0416(18) Uani 1 1 d . . . . .
C14A C 0.6384(5) 0.46262(18) 0.3328(11) 0.045(2) Uani 1 1 d . . . . .
C15A C 0.5669(5) 0.44610(19) 0.2994(12) 0.054(2) Uani 1 1 d . . . . .
H15A H 0.527840 0.457906 0.231572 0.064 Uiso 1 1 calc R U . . .
C16A C 0.5509(5) 0.41265(19) 0.3626(10) 0.047(2) Uani 1 1 d . . . . .
H16A H 0.501136 0.402217 0.338354 0.057 Uiso 1 1 calc R U . . .
C17A C 0.5716(5) 0.37578(19) 0.8744(10) 0.046(2) Uani 1 1 d . . . . .
H17A H 0.601897 0.361871 0.962069 0.056 Uiso 1 1 calc R U . . .
H17B H 0.598565 0.398135 0.847902 0.056 Uiso 1 1 calc R U . . .
C18A C 0.4586(5) 0.3690(2) 0.7249(11) 0.054(2) Uani 1 1 d . . . . .
H18A H 0.446018 0.388990 0.646362 0.064 Uiso 1 1 calc R U . . .
H18B H 0.417139 0.350801 0.718345 0.064 Uiso 1 1 calc R U . . .
C19A C 0.4820(6) 0.3797(2) 0.9199(13) 0.067(3) Uani 1 1 d . . . . .
H19A H 0.466565 0.403853 0.951274 0.081 Uiso 1 1 calc R U . . .
H19B H 0.463438 0.363008 1.011379 0.081 Uiso 1 1 calc R U . . .
C20A C 0.6493(6) 0.5002(2) 0.2703(13) 0.056(2) Uani 1 1 d . . . . .
C21A C 0.6999(15) 0.5599(4) 0.326(4) 0.089(8) Uani 0.57(3) 1 d D U P A 1
H21A H 0.722834 0.561606 0.206458 0.133 Uiso 0.57(3) 1 calc R U P A 1
H21B H 0.735962 0.570582 0.412249 0.133 Uiso 0.57(3) 1 calc R U P A 1
H21C H 0.649035 0.572087 0.328507 0.133 Uiso 0.57(3) 1 calc R U P A 1
N5A N 0.6878(13) 0.5224(4) 0.372(4) 0.068(6) Uani 0.57(3) 1 d D U P A 1
H5NA H 0.707350 0.514781 0.473164 0.082 Uiso 0.57(3) 1 calc R U P A 1
C211 C 0.738(3) 0.5534(7) 0.221(5) 0.101(10) Uani 0.43(3) 1 d D U P A 2
H21D H 0.786417 0.554035 0.148363 0.151 Uiso 0.43(3) 1 calc R U P A 2
H21E H 0.744483 0.568816 0.323689 0.151 Uiso 0.43(3) 1 calc R U P A 2
H21F H 0.693229 0.561280 0.148919 0.151 Uiso 0.43(3) 1 calc R U P A 2
N51 N 0.723(2) 0.5161(6) 0.284(4) 0.074(7) Uani 0.43(3) 1 d D U P A 2
H5N1 H 0.762694 0.504312 0.331397 0.088 Uiso 0.43(3) 1 calc R U P A 2
N1A N 0.6613(4) 0.21034(16) 0.6587(10) 0.0525(18) Uani 1 1 d . . . . .
N2A N 0.5943(4) 0.30170(13) 0.5775(8) 0.0370(15) Uani 1 1 d . . . . .
N3A N 0.5905(4) 0.35952(14) 0.5335(8) 0.0394(15) Uani 1 1 d . . . . .
N4A N 0.6762(6) 0.1282(2) 0.4858(15) 0.096(3) Uani 1 1 d . . . . .
S1A S 0.67675(13) 0.32463(5) 0.2812(3) 0.0482(6) Uani 1 1 d . . . . .
F1A F 0.5523(14) 0.2188(3) 0.0585(16) 0.078(4) Uani 0.68(4) 1 d D U P B 3
F2A F 0.5091(9) 0.1763(5) 0.219(3) 0.086(5) Uani 0.68(4) 1 d D U P B 3
F3A F 0.6256(7) 0.1734(5) 0.114(3) 0.082(5) Uani 0.68(4) 1 d D U P B 3
F11 F 0.601(3) 0.2139(8) 0.061(4) 0.094(9) Uani 0.32(4) 1 d D U P B 4
F21 F 0.4985(12) 0.1899(11) 0.195(5) 0.071(8) Uani 0.32(4) 1 d D U P B 4
F31 F 0.607(2) 0.1625(7) 0.181(5) 0.084(8) Uani 0.32(4) 1 d D U P B 4
F4A F 0.7710(3) 0.45643(12) 0.4503(8) 0.0652(14) Uani 1 1 d . . . . .
O1A O 0.5223(4) 0.29674(14) 0.8454(9) 0.0675(18) Uani 1 1 d . . . . .
O2A O 0.6056(6) 0.51144(18) 0.1495(13) 0.112(3) Uani 1 1 d . . . . .
C1B C 0.8441(4) 0.26408(16) 1.0412(10) 0.0379(18) Uani 1 1 d . . . . .
C2B C 0.8637(5) 0.24824(17) 0.8803(10) 0.0396(18) Uani 1 1 d . . . . .
H2B H 0.886507 0.261676 0.787347 0.047 Uiso 1 1 calc R U . . .
C3B C 0.8498(5) 0.21206(18) 0.8550(10) 0.0415(19) Uani 1 1 d . . . . .
C4B C 0.8121(5) 0.19441(18) 0.9956(12) 0.049(2) Uani 1 1 d . . . . .
C5B C 0.8063(5) 0.24400(18) 1.1755(11) 0.050(2) Uani 1 1 d . . . . .
H5B H 0.791677 0.255079 1.283536 0.060 Uiso 1 1 calc R U . . .
C6B C 0.8321(4) 0.32854(16) 0.9581(10) 0.0360(17) Uani 1 1 d . . . . .
C7B C 0.9095(5) 0.35324(18) 1.1991(10) 0.0422(18) Uani 1 1 d . . . . .
C8B C 0.9050(5) 0.31333(18) 1.2198(11) 0.048(2) Uani 1 1 d . . . . .
C9B C 0.8772(5) 0.1945(2) 0.6852(12) 0.051(2) Uani 1 1 d D . . . .
C10B C 0.7913(6) 0.1567(2) 0.9852(13) 0.063(3) Uani 1 1 d . . . . .
C11B C 0.8461(5) 0.39378(18) 0.9603(11) 0.044(2) Uani 1 1 d . . . . .
C12B C 0.9037(5) 0.41006(19) 0.8562(11) 0.049(2) Uani 1 1 d . . . . .
H12B H 0.950933 0.398447 0.822406 0.059 Uiso 1 1 calc R U . . .
C13B C 0.8876(6) 0.4450(2) 0.8038(13) 0.059(2) Uani 1 1 d . . . . .
C14B C 0.8180(6) 0.46304(19) 0.8514(11) 0.051(2) Uani 1 1 d . . . . .
C15B C 0.7594(6) 0.4446(2) 0.9460(12) 0.054(2) Uani 1 1 d . . . . .
H15B H 0.709820 0.455280 0.969520 0.064 Uiso 1 1 calc R U . . .
C16B C 0.7741(5) 0.4103(2) 1.0058(11) 0.048(2) Uani 1 1 d . . . . .
H16B H 0.735991 0.398411 1.075980 0.057 Uiso 1 1 calc R U . . .
C17B C 0.9965(5) 0.3671(2) 1.2148(12) 0.056(2) Uani 1 1 d . . . . .
H17C H 1.008992 0.386372 1.131902 0.067 Uiso 1 1 calc R U . . .
H17D H 1.037129 0.348487 1.208727 0.067 Uiso 1 1 calc R U . . .
C18B C 0.8865(5) 0.3746(2) 1.3703(11) 0.052(2) Uani 1 1 d . . . . .
H18C H 0.858316 0.396682 1.344789 0.062 Uiso 1 1 calc R U . . .
H18D H 0.858177 0.360707 1.461275 0.062 Uiso 1 1 calc R U . . .
C19B C 0.9768(6) 0.3794(3) 1.4094(13) 0.073(3) Uani 1 1 d . . . . .
H19C H 0.997263 0.363576 1.502839 0.088 Uiso 1 1 calc R U . . .
H19D H 0.992155 0.403876 1.433815 0.088 Uiso 1 1 calc R U . . .
N1B N 0.7904(5) 0.20917(16) 1.1543(10) 0.0541(19) Uani 1 1 d . . . . .
N2B N 0.8583(4) 0.30085(13) 1.0717(8) 0.0381(15) Uani 1 1 d . . . . .
N3B N 0.8632(4) 0.35899(14) 1.0292(8) 0.0399(15) Uani 1 1 d . . . . .
N4B N 0.7726(6) 0.12757(19) 0.9794(15) 0.097(3) Uani 1 1 d . . . . .
S1B S 0.77577(13) 0.32429(5) 0.7779(3) 0.0483(6) Uani 1 1 d . . . . .
C20B C 0.8045(7) 0.5012(2) 0.8005(15) 0.066(3) Uani 0.658(13) 1 d D . P C 5
C21B C 0.8608(12) 0.5628(4) 0.781(3) 0.122(7) Uani 0.658(13) 1 d D U P C 5
H21G H 0.881593 0.569995 0.665124 0.183 Uiso 0.658(13) 1 calc R U P C 5
H21H H 0.892999 0.573092 0.875856 0.183 Uiso 0.658(13) 1 calc R U P C 5
H21I H 0.805984 0.570793 0.793051 0.183 Uiso 0.658(13) 1 calc R U P C 5
O2B O 0.7370(15) 0.5108(5) 0.749(4) 0.092(6) Uani 0.658(13) 1 d D U P C 5
N5B N 0.863(2) 0.5228(6) 0.796(4) 0.094(7) Uani 0.658(13) 1 d D U P C 5
H5NB H 0.910772 0.513486 0.801329 0.113 Uiso 0.658(13) 1 calc R U P C 5
C202 C 0.8045(7) 0.5012(2) 0.8005(15) 0.066(3) Uani 0.342(13) 1 d D U P C 6
C212 C 0.7088(17) 0.5506(5) 0.746(4) 0.084(8) Uani 0.342(13) 1 d D U P C 6
H21J H 0.690540 0.555713 0.624834 0.125 Uiso 0.342(13) 1 calc R U P C 6
H21K H 0.754501 0.565376 0.773778 0.125 Uiso 0.342(13) 1 calc R U P C 6
H21L H 0.666152 0.555388 0.830510 0.125 Uiso 0.342(13) 1 calc R U P C 6
O22 O 0.859(3) 0.5218(10) 0.857(5) 0.072(8) Uani 0.342(13) 1 d D U P C 6
N52 N 0.733(3) 0.5123(9) 0.759(9) 0.093(12) Uani 0.342(13) 1 d D U P C 6
H5N2 H 0.696332 0.496524 0.736487 0.112 Uiso 0.342(13) 1 calc R U P C 6
F1B F 0.9011(15) 0.2182(3) 0.5563(19) 0.084(5) Uani 0.67(4) 1 d D U P D 5
F2B F 0.9464(8) 0.1770(5) 0.710(2) 0.076(4) Uani 0.67(4) 1 d D U P D 5
F3B F 0.8261(8) 0.1746(6) 0.600(3) 0.096(6) Uani 0.67(4) 1 d D U P D 5
F12 F 0.853(3) 0.2118(8) 0.546(3) 0.084(8) Uani 0.33(4) 1 d D U P D 6
F22 F 0.9542(13) 0.1906(11) 0.683(6) 0.090(9) Uani 0.33(4) 1 d D U P D 6
F32 F 0.847(2) 0.1622(6) 0.672(4) 0.082(8) Uani 0.33(4) 1 d D U P D 6
F4B F 0.9423(4) 0.46058(14) 0.6938(10) 0.103(2) Uani 1 1 d . . . . .
O1B O 0.9328(4) 0.29499(13) 1.3355(8) 0.0670(18) Uani 1 1 d . . . . .
O3A O 0.4289(13) 0.5249(6) -0.191(4) 0.123(7) Uani 0.5 1 d D U P E -7
H1O H 0.418673 0.546041 -0.207774 0.185 Uiso 0.5 1 calc R U P E -7
C22A C 0.512(3) 0.4765(12) -0.228(6) 0.146(13) Uani 0.5 1 d D U P E -7
H22A H 0.505064 0.461161 -0.331105 0.218 Uiso 0.5 1 calc R U P E -7
H22B H 0.471978 0.470643 -0.137612 0.218 Uiso 0.5 1 calc R U P E -7
H22C H 0.564679 0.473377 -0.177965 0.218 Uiso 0.5 1 calc R U P E -7
C23A C 0.501(3) 0.5156(12) -0.287(6) 0.170(16) Uani 0.5 1 d D U P E -7
H23A H 0.545963 0.530269 -0.250275 0.204 Uiso 0.5 1 calc R U P E -7
H23B H 0.493224 0.517608 -0.417515 0.204 Uiso 0.5 1 calc R U P E -7
C22B C 1.008(3) 0.5046(12) 1.039(3) 0.114(8) Uani 0.25 1 d D U P F -8
H22D H 1.050268 0.515418 0.970511 0.171 Uiso 0.25 1 calc R U P F -8
H22E H 1.017466 0.479505 1.050260 0.171 Uiso 0.25 1 calc R U P F -8
H22F H 0.957052 0.508429 0.978800 0.171 Uiso 0.25 1 calc R U P F -8
C23B C 1.005(5) 0.5212(19) 1.227(6) 0.136(13) Uani 0.25 1 d D U P F -8
H23C H 1.054562 0.517387 1.292716 0.164 Uiso 0.25 1 calc R U P F -8
H23D H 0.993616 0.546566 1.220625 0.164 Uiso 0.25 1 calc R U P F -8
O3B O 0.941(3) 0.5031(15) 1.307(5) 0.157(13) Uani 0.25 1 d D U P F -8
H2O H 0.898784 0.509530 1.260710 0.236 Uiso 0.25 1 calc R U P F -8
C222 C 1.008(3) 0.5046(12) 1.039(3) 0.114(8) Uani 0.25 1 d D U P G -9
H22G H 1.057354 0.491986 1.021438 0.171 Uiso 0.25 1 calc R U P G -9
H22H H 0.963871 0.491103 0.988805 0.171 Uiso 0.25 1 calc R U P G -9
H22I H 1.010574 0.527387 0.980477 0.171 Uiso 0.25 1 calc R U P G -9
C232 C 0.993(4) 0.510(2) 1.242(4) 0.138(13) Uani 0.25 1 d D U P G -9
H23E H 0.989522 0.487282 1.304436 0.166 Uiso 0.25 1 calc R U P G -9
H23F H 1.036569 0.523834 1.296048 0.166 Uiso 0.25 1 calc R U P G -9
O32 O 0.921(3) 0.5281(14) 1.250(6) 0.170(13) Uani 0.25 1 d D U P G -9
H202 H 0.929997 0.549394 1.266088 0.254 Uiso 0.25 1 calc R U P G -9
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'
S S 0.1246 0.1234 '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
C5A C1A C2A 120.4(6) . . ?
C5A C1A N2A 119.9(6) . . ?
C2A C1A N2A 119.6(7) . . ?
C3A C2A C1A 116.8(7) . . ?
C3A C2A H2A 121.6 . . ?
C1A C2A H2A 121.6 . . ?
C4A C3A C2A 119.6(7) . . ?
C4A C3A C9A 122.4(6) . . ?
C2A C3A C9A 118.0(7) . . ?
N1A C4A C3A 122.6(6) . . ?
N1A C4A C10A 114.6(7) . . ?
C3A C4A C10A 122.7(7) . . ?
N1A C5A C1A 122.2(7) . . ?
N1A C5A H5A 118.9 . . ?
C1A C5A H5A 118.9 . . ?
N3A C6A N2A 105.9(6) . . ?
N3A C6A S1A 128.2(6) . . ?
N2A C6A S1A 125.8(5) . . ?
N3A C7A C8A 100.3(6) . . ?
N3A C7A C17A 119.3(6) . . ?
C8A C7A C17A 114.3(6) . . ?
N3A C7A C18A 121.0(6) . . ?
C8A C7A C18A 113.3(7) . . ?
C17A C7A C18A 89.7(6) . . ?
O1A C8A N2A 125.9(6) . . ?
O1A C8A C7A 126.4(7) . . ?
N2A C8A C7A 107.7(6) . . ?
F11 C9A F21 116.2(19) . . ?
F3A C9A F2A 106.2(10) . . ?
F11 C9A F31 110.1(17) . . ?
F21 C9A F31 105.2(16) . . ?
F3A C9A F1A 106.4(11) . . ?
F2A C9A F1A 103.9(10) . . ?
F11 C9A C3A 105.8(15) . . ?
F21 C9A C3A 110.3(17) . . ?
F3A C9A C3A 116.1(9) . . ?
F2A C9A C3A 111.0(11) . . ?
F31 C9A C3A 109.2(16) . . ?
F1A C9A C3A 112.3(7) . . ?
N4A C10A C4A 175.9(12) . . ?
C12A C11A C16A 118.9(7) . . ?
C12A C11A N3A 120.7(7) . . ?
C16A C11A N3A 120.4(7) . . ?
C11A C12A C13A 118.0(7) . . ?
C11A C12A H12A 121.0 . . ?
C13A C12A H12A 121.0 . . ?
C14A C13A F4A 119.4(7) . . ?
C14A C13A C12A 124.6(8) . . ?
F4A C13A C12A 115.8(7) . . ?
C15A C14A C13A 115.8(7) . . ?
C15A C14A C20A 118.7(8) . . ?
C13A C14A C20A 125.4(8) . . ?
C14A C15A C16A 121.8(8) . . ?
C14A C15A H15A 119.1 . . ?
C16A C15A H15A 119.1 . . ?
C15A C16A C11A 120.8(8) . . ?
C15A C16A H16A 119.6 . . ?
C11A C16A H16A 119.6 . . ?
C19A C17A C7A 87.7(6) . . ?
C19A C17A H17A 114.0 . . ?
C7A C17A H17A 114.0 . . ?
C19A C17A H17B 114.0 . . ?
C7A C17A H17B 114.0 . . ?
H17A C17A H17B 111.2 . . ?
C19A C18A C7A 87.3(6) . . ?
C19A C18A H18A 114.1 . . ?
C7A C18A H18A 114.1 . . ?
C19A C18A H18B 114.1 . . ?
C7A C18A H18B 114.1 . . ?
H18A C18A H18B 111.3 . . ?
C17A C19A C18A 90.9(7) . . ?
C17A C19A H19A 113.5 . . ?
C18A C19A H19A 113.5 . . ?
C17A C19A H19B 113.5 . . ?
C18A C19A H19B 113.5 . . ?
H19A C19A H19B 110.8 . . ?
O2A C20A N5A 119.4(10) . . ?
O2A C20A N51 115.8(12) . . ?
O2A C20A C14A 118.6(9) . . ?
N5A C20A C14A 119.4(11) . . ?
N51 C20A C14A 119.9(13) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C20A N5A C21A 123.7(17) . . ?
C20A N5A H5NA 118.1 . . ?
C21A N5A H5NA 118.1 . . ?
N51 C211 H21D 109.5 . . ?
N51 C211 H21E 109.5 . . ?
H21D C211 H21E 109.5 . . ?
N51 C211 H21F 109.5 . . ?
H21D C211 H21F 109.5 . . ?
H21E C211 H21F 109.5 . . ?
C20A N51 C211 122(2) . . ?
C20A N51 H5N1 118.9 . . ?
C211 N51 H5N1 118.9 . . ?
C5A N1A C4A 118.4(7) . . ?
C8A N2A C6A 111.7(5) . . ?
C8A N2A C1A 124.3(6) . . ?
C6A N2A C1A 124.0(6) . . ?
C6A N3A C11A 123.2(6) . . ?
C6A N3A C7A 114.3(6) . . ?
C11A N3A C7A 122.1(5) . . ?
C2B C1B C5B 119.2(6) . . ?
C2B C1B N2B 121.4(6) . . ?
C5B C1B N2B 119.3(7) . . ?
C1B C2B C3B 120.1(7) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
C4B C3B C2B 116.4(7) . . ?
C4B C3B C9B 123.9(6) . . ?
C2B C3B C9B 119.7(7) . . ?
N1B C4B C3B 125.2(7) . . ?
N1B C4B C10B 112.5(8) . . ?
C3B C4B C10B 122.3(8) . . ?
N1B C5B C1B 122.2(7) . . ?
N1B C5B H5B 118.9 . . ?
C1B C5B H5B 118.9 . . ?
N3B C6B N2B 106.0(6) . . ?
N3B C6B S1B 127.8(5) . . ?
N2B C6B S1B 126.2(5) . . ?
N3B C7B C8B 101.8(6) . . ?
N3B C7B C17B 120.0(7) . . ?
C8B C7B C17B 112.0(7) . . ?
N3B C7B C18B 119.1(6) . . ?
C8B C7B C18B 115.0(7) . . ?
C17B C7B C18B 89.7(6) . . ?
O1B C8B N2B 124.9(6) . . ?
O1B C8B C7B 129.0(8) . . ?
N2B C8B C7B 106.1(6) . . ?
F12 C9B F22 111.1(19) . . ?
F12 C9B F32 106.8(15) . . ?
F22 C9B F32 106.1(16) . . ?
F3B C9B F2B 110.0(10) . . ?
F3B C9B F1B 103.3(11) . . ?
F2B C9B F1B 99.7(10) . . ?
F12 C9B C3B 110.8(13) . . ?
F22 C9B C3B 111(2) . . ?
F3B C9B C3B 117.7(10) . . ?
F32 C9B C3B 110.5(12) . . ?
F2B C9B C3B 111.5(10) . . ?
F1B C9B C3B 112.8(8) . . ?
N4B C10B C4B 177.8(11) . . ?
C12B C11B C16B 122.4(7) . . ?
C12B C11B N3B 118.0(7) . . ?
C16B C11B N3B 119.6(7) . . ?
C11B C12B C13B 116.3(8) . . ?
C11B C12B H12B 121.9 . . ?
C13B C12B H12B 121.9 . . ?
F4B C13B C14B 119.9(7) . . ?
F4B C13B C12B 116.6(8) . . ?
C14B C13B C12B 123.4(8) . . ?
C15B C14B C13B 118.0(7) . . ?
C15B C14B C202 120.0(8) . . ?
C13B C14B C202 122.1(8) . . ?
C15B C14B C20B 120.0(8) . . ?
C13B C14B C20B 122.1(8) . . ?
C14B C15B C16B 120.2(8) . . ?
C14B C15B H15B 119.9 . . ?
C16B C15B H15B 119.9 . . ?
C15B C16B C11B 119.5(8) . . ?
C15B C16B H16B 120.3 . . ?
C11B C16B H16B 120.3 . . ?
C7B C17B C19B 88.4(7) . . ?
C7B C17B H17C 113.9 . . ?
C19B C17B H17C 113.9 . . ?
C7B C17B H17D 113.9 . . ?
C19B C17B H17D 113.9 . . ?
H17C C17B H17D 111.1 . . ?
C19B C18B C7B 88.5(6) . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18D 113.9 . . ?
C7B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C18B C19B C17B 89.8(7) . . ?
C18B C19B H19C 113.7 . . ?
C17B C19B H19C 113.7 . . ?
C18B C19B H19D 113.7 . . ?
C17B C19B H19D 113.7 . . ?
H19C C19B H19D 110.9 . . ?
C4B N1B C5B 116.7(7) . . ?
C6B N2B C8B 112.5(5) . . ?
C6B N2B C1B 125.1(6) . . ?
C8B N2B C1B 122.3(6) . . ?
C6B N3B C11B 123.8(6) . . ?
C6B N3B C7B 113.5(5) . . ?
C11B N3B C7B 122.3(6) . . ?
O2B C20B N5B 119.9(15) . . ?
O2B C20B C14B 119.6(14) . . ?
N5B C20B C14B 120.2(16) . . ?
N5B C21B H21G 109.5 . . ?
N5B C21B H21H 109.5 . . ?
H21G C21B H21H 109.5 . . ?
N5B C21B H21I 109.5 . . ?
H21G C21B H21I 109.5 . . ?
H21H C21B H21I 109.5 . . ?
C20B N5B C21B 128(3) . . ?
C20B N5B H5NB 115.9 . . ?
C21B N5B H5NB 115.9 . . ?
O22 C202 N52 122(2) . . ?
O22 C202 C14B 113.6(17) . . ?
N52 C202 C14B 120.4(19) . . ?
N52 C212 H21J 109.5 . . ?
N52 C212 H21K 109.5 . . ?
H21J C212 H21K 109.5 . . ?
N52 C212 H21L 109.5 . . ?
H21J C212 H21L 109.5 . . ?
H21K C212 H21L 109.5 . . ?
C202 N52 C212 125(4) . . ?
C202 N52 H5N2 117.7 . . ?
C212 N52 H5N2 117.7 . . ?
C23A O3A H1O 109.5 . . ?
C23A C22A H22A 109.5 . . ?
C23A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C23A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O3A C23A C22A 101(2) . . ?
O3A C23A H23A 111.6 . . ?
C22A C23A H23A 111.6 . . ?
O3A C23A H23B 111.6 . . ?
C22A C23A H23B 111.6 . . ?
H23A C23A H23B 109.4 . . ?
C23B C22B H22D 109.5 . . ?
C23B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C23B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O3B C23B C22B 102(2) . . ?
O3B C23B H23C 111.3 . . ?
C22B C23B H23C 111.3 . . ?
O3B C23B H23D 111.3 . . ?
C22B C23B H23D 111.3 . . ?
H23C C23B H23D 109.2 . . ?
C23B O3B H2O 109.5 . . ?
C232 C222 H22G 109.5 . . ?
C232 C222 H22H 109.5 . . ?
H22G C222 H22H 109.5 . . ?
C232 C222 H22I 109.5 . . ?
H22G C222 H22I 109.5 . . ?
H22H C222 H22I 109.5 . . ?
O32 C232 C222 104(3) . . ?
O32 C232 H23E 111.0 . . ?
C222 C232 H23E 111.0 . . ?
O32 C232 H23F 111.0 . . ?
C222 C232 H23F 111.0 . . ?
H23E C232 H23F 109.0 . . ?
C232 O32 H202 109.5 . . ?
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 C5A 1.371(10) . ?
C1A C2A 1.393(10) . ?
C1A N2A 1.432(8) . ?
C2A C3A 1.380(9) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.378(10) . ?
C3A C9A 1.527(11) . ?
C4A N1A 1.337(10) . ?
C4A C10A 1.441(10) . ?
C5A N1A 1.323(9) . ?
C5A H5A 0.9300 . ?
C6A N3A 1.342(8) . ?
C6A N2A 1.407(9) . ?
C6A S1A 1.639(8) . ?
C7A N3A 1.464(10) . ?
C7A C8A 1.512(9) . ?
C7A C17A 1.551(10) . ?
C7A C18A 1.552(11) . ?
C8A O1A 1.220(9) . ?
C8A N2A 1.375(9) . ?
C9A F11 1.26(2) . ?
C9A F21 1.28(2) . ?
C9A F3A 1.293(12) . ?
C9A F2A 1.309(14) . ?
C9A F31 1.33(2) . ?
C9A F1A 1.370(13) . ?
C10A N4A 1.135(10) . ?
C11A C12A 1.352(10) . ?
C11A C16A 1.400(10) . ?
C11A N3A 1.420(9) . ?
C12A C13A 1.385(10) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.370(11) . ?
C13A F4A 1.378(9) . ?
C14A C15A 1.360(12) . ?
C14A C20A 1.493(10) . ?
C15A C16A 1.365(10) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A C19A 1.529(12) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.541(12) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A O2A 1.223(11) . ?
C20A N5A 1.29(2) . ?
C20A N51 1.37(3) . ?
C21A N5A 1.461(17) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
N5A H5NA 0.8600 . ?
C211 N51 1.50(2) . ?
C211 H21D 0.9600 . ?
C211 H21E 0.9600 . ?
C211 H21F 0.9600 . ?
N51 H5N1 0.8600 . ?
C1B C2B 1.366(10) . ?
C1B C5B 1.392(10) . ?
C1B N2B 1.418(8) . ?
C2B C3B 1.390(9) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.378(11) . ?
C3B C9B 1.484(11) . ?
C4B N1B 1.343(10) . ?
C4B C10B 1.460(11) . ?
C5B N1B 1.343(9) . ?
C5B H5B 0.9300 . ?
C6B N3B 1.359(8) . ?
C6B N2B 1.403(9) . ?
C6B S1B 1.630(8) . ?
C7B N3B 1.483(10) . ?
C7B C8B 1.508(10) . ?
C7B C17B 1.537(11) . ?
C7B C18B 1.541(10) . ?
C8B O1B 1.188(9) . ?
C8B N2B 1.417(10) . ?
C9B F12 1.280(18) . ?
C9B F22 1.29(2) . ?
C9B F3B 1.291(13) . ?
C9B F32 1.318(18) . ?
C9B F2B 1.335(13) . ?
C9B F1B 1.360(13) . ?
C10B N4B 1.136(10) . ?
C11B C12B 1.368(11) . ?
C11B C16B 1.385(11) . ?
C11B N3B 1.429(9) . ?
C12B C13B 1.392(10) . ?
C12B H12B 0.9300 . ?
C13B F4B 1.349(10) . ?
C13B C14B 1.383(12) . ?
C14B C15B 1.382(12) . ?
C14B C202 1.496(11) . ?
C14B C20B 1.496(11) . ?
C15B C16B 1.382(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17B C19B 1.542(12) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.535(13) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B O2B 1.24(2) . ?
C20B N5B 1.27(3) . ?
C21B N5B 1.50(2) . ?
C21B H21G 0.9600 . ?
C21B H21H 0.9600 . ?
C21B H21I 0.9600 . ?
N5B H5NB 0.8600 . ?
C202 O22 1.26(5) . ?
C202 N52 1.30(4) . ?
C212 N52 1.50(3) . ?
C212 H21J 0.9600 . ?
C212 H21K 0.9600 . ?
C212 H21L 0.9600 . ?
N52 H5N2 0.8600 . ?
O3A C23A 1.43(3) . ?
O3A H1O 0.8200 . ?
C22A C23A 1.54(2) . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C22B C23B 1.52(3) . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B O3B 1.38(3) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
O3B H2O 0.8200 . ?
C222 C232 1.52(3) . ?
C222 H22G 0.9599 . ?
C222 H22H 0.9600 . ?
C222 H22I 0.9601 . ?
C232 O32 1.38(3) . ?
C232 H23E 0.9700 . ?
C232 H23F 0.9700 . ?
O32 H202 0.8200 . ?
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
N5A H5NA O2B 0.86 2.10 2.93(4) 162 . yes
C15A H15A O2A 0.93 2.56 3.454(13) 160 2_665 yes
C19B H19C F2A 0.97 2.54 3.49(2) 163 4_557 yes
C22A H22B O2A 0.96 2.56 3.43(5) 149 2_665 yes
