#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:25:31 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/88/7248832.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_7248832
loop_
_publ_author_name
'Prashanth, Jupally'
'Voronin, Alexander P.'
'Surov, Artem O.'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Design of pyrazine cocrystals of enzalutamide: a lead from 1,4-dioxane
 solvates
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              3851
_journal_page_last               3866
_journal_paper_doi               10.1039/D4CE00566J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C21 H16 F4 N4 O2 S), 0.5(C4 H4 N2)'
_chemical_formula_sum            'C44 H34 F8 N9 O4 S2'
_chemical_formula_weight         968.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                99.742(2)
_cell_angle_beta                 94.952(2)
_cell_angle_gamma                117.376(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6684(9)
_cell_length_b                   12.5374(10)
_cell_length_c                   17.0985(13)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.36
_cell_volume                     2150.4(3)
_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  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32888
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.991
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6599
_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            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       plate
_exptl_crystal_F_000             994
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         9833
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+1.3697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8038
_reflns_number_total             9833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00566j2.cif
_cod_data_source_block           KB963_0m
_cod_depositor_comments
'Adding full bibliography for 7248830--7248833.cif.'
_cod_database_code               7248832
_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   0.956
_shelx_estimated_absorpt_t_max   0.962
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.35518(15) -0.26851(14) 0.81278(9) 0.0160(3) Uani 1 1 d . . . . .
C2A C 0.30146(16) -0.38391(15) 0.76039(10) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.252386 -0.399887 0.708477 0.025 Uiso 1 1 calc R U . . .
C3A C 0.32008(16) -0.47575(14) 0.78452(10) 0.0205(3) Uani 1 1 d . . . . .
C4A C 0.39422(15) -0.45042(14) 0.86068(10) 0.0179(3) Uani 1 1 d . . . . .
C5A C 0.44706(16) -0.33418(15) 0.91260(9) 0.0199(3) Uani 1 1 d . . . . .
H5A H 0.497000 -0.317340 0.964384 0.024 Uiso 1 1 calc R U . . .
C6A C 0.42672(15) -0.24240(15) 0.88863(9) 0.0184(3) Uani 1 1 d . . . . .
H6A H 0.461600 -0.163040 0.923982 0.022 Uiso 1 1 calc R U . . .
C7A C 0.41041(15) -0.10303(14) 0.73747(9) 0.0172(3) Uani 1 1 d . . . . .
C8A C 0.23555(15) -0.05952(14) 0.75154(9) 0.0177(3) Uani 1 1 d . . . . .
C9A C 0.22658(15) -0.15717(14) 0.79668(9) 0.0173(3) Uani 1 1 d . . . . .
C11A C 0.41873(16) -0.54332(15) 0.88674(10) 0.0218(3) Uani 1 1 d . . . . .
C12A C 0.11465(16) -0.11213(16) 0.68509(10) 0.0234(3) Uani 1 1 d . . . . .
H12A H 0.121755 -0.048218 0.656780 0.035 Uiso 1 1 calc R U . . .
H12B H 0.035561 -0.139267 0.709127 0.035 Uiso 1 1 calc R U . . .
H12C H 0.109017 -0.182694 0.646694 0.035 Uiso 1 1 calc R U . . .
C13A C 0.25251(17) 0.05479(15) 0.81044(10) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.266665 0.119858 0.781686 0.035 Uiso 1 1 calc R U . . .
H13B H 0.328459 0.084200 0.853597 0.035 Uiso 1 1 calc R U . . .
H13C H 0.173300 0.033792 0.833899 0.035 Uiso 1 1 calc R U . . .
C14A C 0.39673(15) 0.04163(15) 0.66133(10) 0.0191(3) Uani 1 1 d . . . . .
C15A C 0.46736(16) 0.16877(15) 0.68899(10) 0.0232(3) Uani 1 1 d . . . . .
H15A H 0.494395 0.205918 0.745240 0.028 Uiso 1 1 calc R U . . .
C16A C 0.49772(17) 0.24059(16) 0.63298(11) 0.0263(4) Uani 1 1 d . . . . .
H16D H 0.548969 0.327784 0.651681 0.032 Uiso 0.426(3) 1 calc R U P A 2
C17A C 0.45624(16) 0.19018(16) 0.55075(10) 0.0237(3) Uani 1 1 d . . . . .
C18A C 0.38805(17) 0.06264(16) 0.52517(11) 0.0254(4) Uani 1 1 d . . . . .
H18A H 0.360341 0.025804 0.468884 0.030 Uiso 0.574(3) 1 calc R U P A 1
C19A C 0.35887(17) -0.01317(15) 0.57926(10) 0.0224(3) Uani 1 1 d . . . . .
H19A H 0.314004 -0.100585 0.560477 0.027 Uiso 1 1 calc R U . . .
C20A C 0.48297(17) 0.27593(16) 0.49461(11) 0.0271(4) Uani 1 1 d . . . . .
C21A C 0.38623(19) 0.33638(18) 0.39075(11) 0.0299(4) Uani 1 1 d . . . . .
H21A H 0.449723 0.337927 0.356377 0.045 Uiso 1 1 calc R U . . .
H21B H 0.414990 0.420407 0.421918 0.045 Uiso 1 1 calc R U . . .
H21C H 0.299804 0.304039 0.356887 0.045 Uiso 1 1 calc R U . . .
N1A N 0.33352(12) -0.17551(12) 0.78608(8) 0.0162(3) Uani 1 1 d . . . . .
N2A N 0.35582(13) -0.03479(12) 0.71807(8) 0.0175(3) Uani 1 1 d . . . . .
N3A N 0.37759(15) 0.25723(14) 0.44587(8) 0.0234(3) Uani 1 1 d . . . . .
H3NA H 0.302(2) 0.200(2) 0.4489(13) 0.033(6) Uiso 1 1 d . . . . .
N4A N 0.44017(16) -0.61552(14) 0.90766(9) 0.0303(3) Uani 1 1 d . . . . .
O1A O 0.14485(11) -0.20744(11) 0.83562(7) 0.0227(2) Uani 1 1 d . . . . .
O2A O 0.59368(14) 0.35920(15) 0.49694(11) 0.0572(5) Uani 1 1 d . . . . .
S1A S 0.54417(4) -0.10230(4) 0.71295(3) 0.02241(10) Uani 1 1 d . . . . .
C10A C 0.2563(3) -0.6037(2) 0.72873(19) 0.0279(7) Uani 0.843(4) 1 d D U P B 1
F1A F 0.18414(18) -0.69007(13) 0.76747(11) 0.0479(5) Uani 0.843(4) 1 d D U P B 1
F2A F 0.1664(2) -0.6189(2) 0.66913(14) 0.0405(5) Uani 0.843(4) 1 d D U P B 1
F3A F 0.34427(15) -0.63354(15) 0.70605(12) 0.0500(7) Uani 0.843(4) 1 d D U P B 1
C10D C 0.284(2) -0.5807(18) 0.7278(11) 0.056(5) Uani 0.157(4) 1 d D U P B 2
F1D F 0.2632(14) -0.6902(8) 0.7412(6) 0.061(4) Uani 0.157(4) 1 d D U P B 2
F2D F 0.2207(17) -0.5990(13) 0.6547(8) 0.056(3) Uani 0.157(4) 1 d D U P B 2
F3D F 0.3363(9) -0.5807(8) 0.6541(5) 0.050(3) Uani 0.157(4) 1 d D U P B 2
F4A F 0.57385(18) 0.36051(15) 0.65514(10) 0.0277(5) Uani 0.574(3) 1 d . . P A 3
F4D F 0.3496(3) 0.0163(2) 0.45152(13) 0.0303(7) Uani 0.426(3) 1 d . . P A 4
C1B C 0.79620(15) -0.08351(14) 0.91621(9) 0.0178(3) Uani 1 1 d . . . . .
C2B C 0.76093(15) -0.18732(15) 0.85543(10) 0.0189(3) Uani 1 1 d . . . . .
H2B H 0.734699 -0.188697 0.800944 0.023 Uiso 1 1 calc R U . . .
C3B C 0.76410(16) -0.28940(15) 0.87458(10) 0.0190(3) Uani 1 1 d . . . . .
C4B C 0.79764(15) -0.28844(15) 0.95548(10) 0.0191(3) Uani 1 1 d . . . . .
C5B C 0.83237(16) -0.18342(15) 1.01575(10) 0.0216(3) Uani 1 1 d . . . . .
H5B H 0.855238 -0.182638 1.070612 0.026 Uiso 1 1 calc R U . . .
C6B C 0.83378(16) -0.08037(15) 0.99628(10) 0.0203(3) Uani 1 1 d . . . . .
H6B H 0.860258 -0.007881 1.037327 0.024 Uiso 1 1 calc R U . . .
C7B C 0.85030(15) 0.08606(14) 0.84129(9) 0.0177(3) Uani 1 1 d . . . . .
C8B C 0.76407(15) 0.19717(14) 0.91836(9) 0.0176(3) Uani 1 1 d . . . . .
C9B C 0.72854(15) 0.07672(14) 0.94265(9) 0.0174(3) Uani 1 1 d . . . . .
C10B C 0.73023(17) -0.39656(15) 0.80524(10) 0.0219(3) Uani 1 1 d . . . . .
C11B C 0.79670(16) -0.39208(15) 0.98197(10) 0.0208(3) Uani 1 1 d . . . . .
C12B C 0.64201(16) 0.20595(16) 0.89033(10) 0.0219(3) Uani 1 1 d . . . . .
H12D H 0.668195 0.286684 0.878065 0.033 Uiso 1 1 calc R U . . .
H12E H 0.589850 0.196438 0.933150 0.033 Uiso 1 1 calc R U . . .
H12F H 0.589347 0.140372 0.841715 0.033 Uiso 1 1 calc R U . . .
C13B C 0.85605(16) 0.30088(15) 0.99159(9) 0.0205(3) Uani 1 1 d . . . . .
H13D H 0.932685 0.290743 1.006989 0.031 Uiso 1 1 calc R U . . .
H13E H 0.809321 0.297297 1.036856 0.031 Uiso 1 1 calc R U . . .
H13F H 0.885009 0.380997 0.977799 0.031 Uiso 1 1 calc R U . . .
C14B C 0.86410(15) 0.26735(14) 0.79668(9) 0.0175(3) Uani 1 1 d . . . . .
C15B C 0.79896(16) 0.21927(15) 0.71689(9) 0.0194(3) Uani 1 1 d . . . . .
H15B H 0.736901 0.134020 0.697829 0.023 Uiso 1 1 calc R U . . .
C16B C 0.82706(16) 0.29913(15) 0.66592(9) 0.0197(3) Uani 1 1 d . . . . .
C17B C 0.91467(15) 0.42491(14) 0.69086(9) 0.0180(3) Uani 1 1 d . . . . .
C18B C 0.97741(16) 0.46940(15) 0.77150(10) 0.0192(3) Uani 1 1 d . . . . .
H18B H 1.037861 0.555013 0.790870 0.023 Uiso 1 1 calc R U . . .
C19B C 0.95413(16) 0.39221(15) 0.82433(10) 0.0197(3) Uani 1 1 d . . . . .
H19B H 0.999284 0.424403 0.878877 0.024 Uiso 1 1 calc R U . . .
C20B C 0.95094(16) 0.51496(15) 0.63720(9) 0.0195(3) Uani 1 1 d . . . . .
C21B C 0.88651(18) 0.57802(17) 0.52174(11) 0.0293(4) Uani 1 1 d . . . . .
H21D H 0.972372 0.599423 0.506862 0.044 Uiso 1 1 calc R U . . .
H21E H 0.886928 0.653313 0.549533 0.044 Uiso 1 1 calc R U . . .
H21F H 0.818203 0.538054 0.472877 0.044 Uiso 1 1 calc R U . . .
N1B N 0.79187(13) 0.02215(12) 0.89949(8) 0.0176(3) Uani 1 1 d . . . . .
N2B N 0.83354(13) 0.18640(12) 0.85118(8) 0.0178(3) Uani 1 1 d . . . . .
N3B N 0.85979(15) 0.49377(14) 0.57514(9) 0.0240(3) Uani 1 1 d . . . . .
H3NB H 0.779(2) 0.433(2) 0.5666(12) 0.030(5) Uiso 1 1 d . . . . .
N4B N 0.79891(15) -0.46815(14) 1.00981(9) 0.0276(3) Uani 1 1 d . . . . .
O1B O 0.66227(11) 0.03668(10) 0.99183(7) 0.0209(2) Uani 1 1 d . . . . .
O2B O 1.06211(11) 0.60502(11) 0.65265(7) 0.0252(3) Uani 1 1 d . . . . .
F1B F 0.61183(10) -0.43563(9) 0.76084(6) 0.0296(2) Uani 1 1 d . . . . .
F2B F 0.81582(10) -0.36431(10) 0.75517(6) 0.0319(2) Uani 1 1 d . . . . .
F3B F 0.72787(13) -0.49405(10) 0.82790(6) 0.0409(3) Uani 1 1 d . . . . .
F4B F 0.76501(10) 0.24929(9) 0.58763(6) 0.0281(2) Uani 1 1 d . . . . .
S1B S 0.92650(4) 0.04354(4) 0.77620(2) 0.02262(10) Uani 1 1 d . . . . .
C22 C 0.07711(19) 0.11903(17) 0.53099(11) 0.0319(4) Uani 1 1 d . . . . .
H22 H 0.130761 0.204627 0.555273 0.038 Uiso 1 1 calc R U . . .
C23 C -0.03212(19) 0.05180(18) 0.56208(11) 0.0313(4) Uani 1 1 d . . . . .
H23 H -0.052152 0.092671 0.606476 0.038 Uiso 1 1 calc R U . . .
N5 N 0.11021(15) 0.06846(15) 0.46824(9) 0.0292(3) Uani 1 1 d . . . . .
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
C6A C1A C2A 121.79(14) . . ?
C6A C1A N1A 120.31(14) . . ?
C2A C1A N1A 117.90(14) . . ?
C3A C2A C1A 119.28(15) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
C10D C3A C2A 117.7(8) . . ?
C10D C3A C4A 121.6(9) . . ?
C2A C3A C4A 119.76(15) . . ?
C2A C3A C10A 119.34(18) . . ?
C4A C3A C10A 120.87(17) . . ?
C5A C4A C3A 120.18(14) . . ?
C5A C4A C11A 118.71(15) . . ?
C3A C4A C11A 121.10(15) . . ?
C4A C5A C6A 119.96(15) . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A C5A 119.01(15) . . ?
C1A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
N2A C7A N1A 106.88(13) . . ?
N2A C7A S1A 128.40(12) . . ?
N1A C7A S1A 124.70(11) . . ?
N2A C8A C9A 100.76(11) . . ?
N2A C8A C13A 111.68(13) . . ?
C9A C8A C13A 110.16(13) . . ?
N2A C8A C12A 111.92(13) . . ?
C9A C8A C12A 110.46(13) . . ?
C13A C8A C12A 111.40(13) . . ?
O1A C9A N1A 126.08(14) . . ?
O1A C9A C8A 127.16(14) . . ?
N1A C9A C8A 106.75(12) . . ?
N4A C11A C4A 178.93(19) . . ?
C8A C12A H12A 109.5 . . ?
C8A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C8A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C8A C13A H13A 109.5 . . ?
C8A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C8A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15A C14A C19A 120.97(15) . . ?
C15A C14A N2A 119.68(14) . . ?
C19A C14A N2A 119.26(14) . . ?
C16A C15A C14A 118.54(16) . . ?
C16A C15A H15A 120.7 . . ?
C14A C15A H15A 120.7 . . ?
F4A C16A C15A 121.32(17) . . ?
F4A C16A C17A 116.17(16) . . ?
C15A C16A C17A 122.41(16) . . ?
C15A C16A H16D 118.8 . . ?
C17A C16A H16D 118.8 . . ?
C16A C17A C18A 117.45(15) . . ?
C16A C17A C20A 118.72(15) . . ?
C18A C17A C20A 123.80(16) . . ?
F4D C18A C17A 118.05(18) . . ?
F4D C18A C19A 119.92(19) . . ?
C17A C18A C19A 122.01(16) . . ?
C17A C18A H18A 119.0 . . ?
C19A C18A H18A 119.0 . . ?
C14A C19A C18A 118.50(15) . . ?
C14A C19A H19A 120.8 . . ?
C18A C19A H19A 120.8 . . ?
O2A C20A N3A 123.36(16) . . ?
O2A C20A C17A 121.66(16) . . ?
N3A C20A C17A 114.91(15) . . ?
N3A C21A H21A 109.5 . . ?
N3A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N3A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C9A N1A C7A 112.18(12) . . ?
C9A N1A C1A 124.59(12) . . ?
C7A N1A C1A 122.80(12) . . ?
C7A N2A C14A 124.18(13) . . ?
C7A N2A C8A 113.41(12) . . ?
C14A N2A C8A 121.83(12) . . ?
C20A N3A C21A 121.57(15) . . ?
C20A N3A H3NA 119.0(14) . . ?
C21A N3A H3NA 119.4(14) . . ?
F3A C10A F2A 114.7(3) . . ?
F3A C10A F1A 105.3(2) . . ?
F2A C10A F1A 101.7(2) . . ?
F3A C10A C3A 111.6(2) . . ?
F2A C10A C3A 112.3(2) . . ?
F1A C10A C3A 110.5(2) . . ?
F2D C10D F1D 108.9(16) . . ?
F2D C10D C3A 120.3(16) . . ?
F1D C10D C3A 126.7(13) . . ?
F2D C10D F3D 54.0(11) . . ?
F1D C10D F3D 101.5(16) . . ?
C3A C10D F3D 122.8(14) . . ?
C2B C1B C6B 120.88(14) . . ?
C2B C1B N1B 121.51(14) . . ?
C6B C1B N1B 117.58(14) . . ?
C1B C2B C3B 119.66(15) . . ?
C1B C2B H2B 120.2 . . ?
C3B C2B H2B 120.2 . . ?
C2B C3B C4B 119.73(15) . . ?
C2B C3B C10B 116.75(14) . . ?
C4B C3B C10B 123.52(14) . . ?
C5B C4B C3B 119.73(14) . . ?
C5B C4B C11B 116.28(14) . . ?
C3B C4B C11B 123.98(15) . . ?
C6B C5B C4B 120.41(15) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C1B 119.50(15) . . ?
C5B C6B H6B 120.2 . . ?
C1B C6B H6B 120.2 . . ?
N2B C7B N1B 106.76(12) . . ?
N2B C7B S1B 128.29(12) . . ?
N1B C7B S1B 124.93(11) . . ?
N2B C8B C9B 100.93(11) . . ?
N2B C8B C12B 111.99(13) . . ?
C9B C8B C12B 111.37(13) . . ?
N2B C8B C13B 112.28(13) . . ?
C9B C8B C13B 106.56(13) . . ?
C12B C8B C13B 112.94(13) . . ?
O1B C9B N1B 126.00(14) . . ?
O1B C9B C8B 127.17(14) . . ?
N1B C9B C8B 106.78(12) . . ?
F3B C10B F2B 107.17(13) . . ?
F3B C10B F1B 106.95(14) . . ?
F2B C10B F1B 106.27(13) . . ?
F3B C10B C3B 113.78(13) . . ?
F2B C10B C3B 111.21(14) . . ?
F1B C10B C3B 111.06(13) . . ?
N4B C11B C4B 173.96(18) . . ?
C8B C12B H12D 109.5 . . ?
C8B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C8B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C8B C13B H13D 109.5 . . ?
C8B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C8B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C15B C14B C19B 120.74(14) . . ?
C15B C14B N2B 118.82(14) . . ?
C19B C14B N2B 120.41(14) . . ?
C16B C15B C14B 118.01(15) . . ?
C16B C15B H15B 121.0 . . ?
C14B C15B H15B 121.0 . . ?
F4B C16B C15B 116.92(14) . . ?
F4B C16B C17B 119.61(13) . . ?
C15B C16B C17B 123.47(15) . . ?
C16B C17B C18B 116.62(14) . . ?
C16B C17B C20B 125.40(14) . . ?
C18B C17B C20B 117.93(14) . . ?
C19B C18B C17B 121.83(15) . . ?
C19B C18B H18B 119.1 . . ?
C17B C18B H18B 119.1 . . ?
C18B C19B C14B 119.31(15) . . ?
C18B C19B H19B 120.3 . . ?
C14B C19B H19B 120.3 . . ?
O2B C20B N3B 122.84(15) . . ?
O2B C20B C17B 119.17(14) . . ?
N3B C20B C17B 117.98(14) . . ?
N3B C21B H21D 109.5 . . ?
N3B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N3B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C9B N1B C7B 111.63(12) . . ?
C9B N1B C1B 121.96(12) . . ?
C7B N1B C1B 126.40(12) . . ?
C7B N2B C14B 124.02(13) . . ?
C7B N2B C8B 113.20(12) . . ?
C14B N2B C8B 122.34(12) . . ?
C20B N3B C21B 121.17(15) . . ?
C20B N3B H3NB 122.6(13) . . ?
C21B N3B H3NB 116.0(13) . . ?
N5 C22 C23 122.40(17) . . ?
N5 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
N5 C23 C22 121.89(17) 2_556 . ?
N5 C23 H23 119.1 2_556 . ?
C22 C23 H23 119.1 . . ?
C23 N5 C22 115.71(15) 2_556 . ?
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 C6A 1.380(2) . ?
C1A C2A 1.385(2) . ?
C1A N1A 1.4362(19) . ?
C2A C3A 1.385(2) . ?
C2A H2A 0.9500 . ?
C3A C10D 1.36(2) . ?
C3A C4A 1.399(2) . ?
C3A C10A 1.516(3) . ?
C4A C5A 1.391(2) . ?
C4A C11A 1.448(2) . ?
C5A C6A 1.394(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A N2A 1.3448(19) . ?
C7A N1A 1.3986(19) . ?
C7A S1A 1.6470(16) . ?
C8A N2A 1.4804(19) . ?
C8A C9A 1.524(2) . ?
C8A C13A 1.524(2) . ?
C8A C12A 1.527(2) . ?
C9A O1A 1.2037(18) . ?
C9A N1A 1.3898(19) . ?
C11A N4A 1.146(2) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A C15A 1.383(2) . ?
C14A C19A 1.387(2) . ?
C14A N2A 1.4357(19) . ?
C15A C16A 1.382(2) . ?
C15A H15A 0.9500 . ?
C16A F4A 1.309(2) . ?
C16A C17A 1.382(3) . ?
C16A H16D 0.9500 . ?
C17A C18A 1.384(2) . ?
C17A C20A 1.506(2) . ?
C18A F4D 1.241(3) . ?
C18A C19A 1.389(2) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C20A O2A 1.224(2) . ?
C20A N3A 1.324(2) . ?
C21A N3A 1.457(2) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
N3A H3NA 0.85(2) . ?
C10A F3A 1.310(3) . ?
C10A F2A 1.320(3) . ?
C10A F1A 1.349(3) . ?
C10D F2D 1.325(17) . ?
C10D F1D 1.343(18) . ?
C10D F3D 1.446(18) . ?
C1B C2B 1.385(2) . ?
C1B C6B 1.390(2) . ?
C1B N1B 1.4235(19) . ?
C2B C3B 1.389(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.401(2) . ?
C3B C10B 1.503(2) . ?
C4B C5B 1.392(2) . ?
C4B C11B 1.442(2) . ?
C5B C6B 1.381(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B N2B 1.345(2) . ?
C7B N1B 1.4076(19) . ?
C7B S1B 1.6491(15) . ?
C8B N2B 1.4845(18) . ?
C8B C9B 1.514(2) . ?
C8B C12B 1.521(2) . ?
C8B C13B 1.531(2) . ?
C9B O1B 1.2064(18) . ?
C9B N1B 1.3953(19) . ?
C10B F3B 1.3327(18) . ?
C10B F2B 1.3368(19) . ?
C10B F1B 1.3399(19) . ?
C11B N4B 1.145(2) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B C15B 1.387(2) . ?
C14B C19B 1.389(2) . ?
C14B N2B 1.4389(19) . ?
C15B C16B 1.383(2) . ?
C15B H15B 0.9500 . ?
C16B F4B 1.3566(18) . ?
C16B C17B 1.389(2) . ?
C17B C18B 1.392(2) . ?
C17B C20B 1.508(2) . ?
C18B C19B 1.387(2) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20B O2B 1.233(2) . ?
C20B N3B 1.333(2) . ?
C21B N3B 1.456(2) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
N3B H3NB 0.88(2) . ?
C22 N5 1.330(2) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 N5 1.328(2) 2_556 ?
C23 H23 0.9500 . ?
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 N5 0.85(2) 2.18(2) 3.034(2) 173(2) . yes
N3B H3NB O2A 0.88(2) 2.07(2) 2.825(2) 143.3(18) . yes
C2A H2A O2B 0.95 2.37 3.144(2) 138.1 1_445 yes
C12A H12C O2B 0.98 2.48 3.246(2) 134.7 1_445 yes
C13B H13F N4B 0.98 2.53 3.230(2) 128.7 1_565 yes
C22 H22 F2A^a 0.95 2.53 3.355(3) 145.0 1_565 yes
C18B H18B O1A 0.95 2.58 3.505(2) 164.4 1_665 yes
C6A H6A O1B 0.95 2.50 3.338(2) 146.9 . yes
C15B H15B S1A 0.95 2.85 3.7346(16) 155.0 . yes
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(2) . . . . ?
N1A C1A C2A C3A -179.70(14) . . . . ?
C1A C2A C3A C10D -169.9(11) . . . . ?
C1A C2A C3A C4A -0.9(2) . . . . ?
C1A C2A C3A C10A 177.32(17) . . . . ?
C10D C3A C4A C5A 169.7(11) . . . . ?
C2A C3A C4A C5A 1.2(2) . . . . ?
C10A C3A C4A C5A -177.08(18) . . . . ?
C10D C3A C4A C11A -9.6(11) . . . . ?
C2A C3A C4A C11A -178.16(15) . . . . ?
C10A C3A C4A C11A 3.6(3) . . . . ?
C3A C4A C5A C6A -0.3(2) . . . . ?
C11A C4A C5A C6A 179.04(14) . . . . ?
C2A C1A C6A C5A 1.0(2) . . . . ?
N1A C1A C6A C5A -179.46(13) . . . . ?
C4A C5A C6A C1A -0.8(2) . . . . ?
N2A C8A C9A O1A 179.13(16) . . . . ?
C13A C8A C9A O1A 61.1(2) . . . . ?
C12A C8A C9A O1A -62.4(2) . . . . ?
N2A C8A C9A N1A 0.58(15) . . . . ?
C13A C8A C9A N1A -117.47(14) . . . . ?
C12A C8A C9A N1A 119.04(14) . . . . ?
C19A C14A C15A C16A 1.1(2) . . . . ?
N2A C14A C15A C16A -175.59(15) . . . . ?
C14A C15A C16A F4A -173.99(17) . . . . ?
C14A C15A C16A C17A 2.3(3) . . . . ?
F4A C16A C17A C18A 172.94(17) . . . . ?
C15A C16A C17A C18A -3.5(3) . . . . ?
F4A C16A C17A C20A -9.3(3) . . . . ?
C15A C16A C17A C20A 174.29(16) . . . . ?
C16A C17A C18A F4D 179.6(2) . . . . ?
C20A C17A C18A F4D 1.9(3) . . . . ?
C16A C17A C18A C19A 1.5(3) . . . . ?
C20A C17A C18A C19A -176.21(16) . . . . ?
C15A C14A C19A C18A -3.0(2) . . . . ?
N2A C14A C19A C18A 173.68(14) . . . . ?
F4D C18A C19A C14A -176.4(2) . . . . ?
C17A C18A C19A C14A 1.7(3) . . . . ?
C16A C17A C20A O2A 53.6(3) . . . . ?
C18A C17A C20A O2A -128.7(2) . . . . ?
C16A C17A C20A N3A -123.61(18) . . . . ?
C18A C17A C20A N3A 54.0(2) . . . . ?
O1A C9A N1A C7A -179.95(15) . . . . ?
C8A C9A N1A C7A -1.38(17) . . . . ?
O1A C9A N1A C1A 7.4(3) . . . . ?
C8A C9A N1A C1A -174.01(13) . . . . ?
N2A C7A N1A C9A 1.64(17) . . . . ?
S1A C7A N1A C9A 179.97(12) . . . . ?
N2A C7A N1A C1A 174.42(13) . . . . ?
S1A C7A N1A C1A -7.3(2) . . . . ?
C6A C1A N1A C9A -90.68(19) . . . . ?
C2A C1A N1A C9A 88.90(18) . . . . ?
C6A C1A N1A C7A 97.45(18) . . . . ?
C2A C1A N1A C7A -82.97(18) . . . . ?
N1A C7A N2A C14A -172.64(14) . . . . ?
S1A C7A N2A C14A 9.1(2) . . . . ?
N1A C7A N2A C8A -1.23(18) . . . . ?
S1A C7A N2A C8A -179.47(12) . . . . ?
C15A C14A N2A C7A -106.42(18) . . . . ?
C19A C14A N2A C7A 76.9(2) . . . . ?
C15A C14A N2A C8A 82.86(19) . . . . ?
C19A C14A N2A C8A -93.86(18) . . . . ?
C9A C8A N2A C7A 0.41(17) . . . . ?
C13A C8A N2A C7A 117.34(15) . . . . ?
C12A C8A N2A C7A -116.98(15) . . . . ?
C9A C8A N2A C14A 172.05(13) . . . . ?
C13A C8A N2A C14A -71.02(18) . . . . ?
C12A C8A N2A C14A 54.66(19) . . . . ?
O2A C20A N3A C21A -0.2(3) . . . . ?
C17A C20A N3A C21A 176.94(15) . . . . ?
C2A C3A C10A F3A 117.0(2) . . . . ?
C4A C3A C10A F3A -64.7(3) . . . . ?
C2A C3A C10A F2A -13.4(3) . . . . ?
C4A C3A C10A F2A 164.9(2) . . . . ?
C2A C3A C10A F1A -126.1(2) . . . . ?
C4A C3A C10A F1A 52.1(3) . . . . ?
C2A C3A C10D F2D -7(2) . . . . ?
C4A C3A C10D F2D -176.1(14) . . . . ?
C2A C3A C10D F1D -162.2(18) . . . . ?
C4A C3A C10D F1D 29(3) . . . . ?
C2A C3A C10D F3D 57(2) . . . . ?
C4A C3A C10D F3D -111.8(15) . . . . ?
C6B C1B C2B C3B -0.5(2) . . . . ?
N1B C1B C2B C3B -178.74(14) . . . . ?
C1B C2B C3B C4B 2.6(2) . . . . ?
C1B C2B C3B C10B -177.43(14) . . . . ?
C2B C3B C4B C5B -2.4(2) . . . . ?
C10B C3B C4B C5B 177.64(15) . . . . ?
C2B C3B C4B C11B 176.43(15) . . . . ?
C10B C3B C4B C11B -3.5(2) . . . . ?
C3B C4B C5B C6B 0.1(2) . . . . ?
C11B C4B C5B C6B -178.87(15) . . . . ?
C4B C5B C6B C1B 2.0(2) . . . . ?
C2B C1B C6B C5B -1.8(2) . . . . ?
N1B C1B C6B C5B 176.45(14) . . . . ?
N2B C8B C9B O1B -174.46(16) . . . . ?
C12B C8B C9B O1B -55.4(2) . . . . ?
C13B C8B C9B O1B 68.1(2) . . . . ?
N2B C8B C9B N1B 7.95(16) . . . . ?
C12B C8B C9B N1B 126.96(13) . . . . ?
C13B C8B C9B N1B -109.46(14) . . . . ?
C2B C3B C10B F3B -176.43(14) . . . . ?
C4B C3B C10B F3B 3.5(2) . . . . ?
C2B C3B C10B F2B 62.43(19) . . . . ?
C4B C3B C10B F2B -117.65(17) . . . . ?
C2B C3B C10B F1B -55.70(19) . . . . ?
C4B C3B C10B F1B 124.22(16) . . . . ?
C19B C14B C15B C16B 0.4(2) . . . . ?
N2B C14B C15B C16B 178.31(14) . . . . ?
C14B C15B C16B F4B 178.12(13) . . . . ?
C14B C15B C16B C17B -1.4(2) . . . . ?
F4B C16B C17B C18B -178.41(14) . . . . ?
C15B C16B C17B C18B 1.1(2) . . . . ?
F4B C16B C17B C20B -1.1(2) . . . . ?
C15B C16B C17B C20B 178.41(15) . . . . ?
C16B C17B C18B C19B 0.2(2) . . . . ?
C20B C17B C18B C19B -177.31(14) . . . . ?
C17B C18B C19B C14B -1.1(2) . . . . ?
C15B C14B C19B C18B 0.8(2) . . . . ?
N2B C14B C19B C18B -177.05(14) . . . . ?
C16B C17B C20B O2B -148.72(16) . . . . ?
C18B C17B C20B O2B 28.5(2) . . . . ?
C16B C17B C20B N3B 32.0(2) . . . . ?
C18B C17B C20B N3B -150.79(15) . . . . ?
O1B C9B N1B C7B 174.18(16) . . . . ?
C8B C9B N1B C7B -8.19(17) . . . . ?
O1B C9B N1B C1B -7.1(2) . . . . ?
C8B C9B N1B C1B 170.48(14) . . . . ?
N2B C7B N1B C9B 4.66(18) . . . . ?
S1B C7B N1B C9B -176.59(12) . . . . ?
N2B C7B N1B C1B -173.94(14) . . . . ?
S1B C7B N1B C1B 4.8(2) . . . . ?
C2B C1B N1B C9B 129.45(16) . . . . ?
C6B C1B N1B C9B -48.8(2) . . . . ?
C2B C1B N1B C7B -52.1(2) . . . . ?
C6B C1B N1B C7B 129.64(16) . . . . ?
N1B C7B N2B C14B -171.54(14) . . . . ?
S1B C7B N2B C14B 9.8(2) . . . . ?
N1B C7B N2B C8B 1.02(18) . . . . ?
S1B C7B N2B C8B -177.67(12) . . . . ?
C15B C14B N2B C7B 60.7(2) . . . . ?
C19B C14B N2B C7B -121.37(17) . . . . ?
C15B C14B N2B C8B -111.18(17) . . . . ?
C19B C14B N2B C8B 66.7(2) . . . . ?
C9B C8B N2B C7B -5.59(17) . . . . ?
C12B C8B N2B C7B -124.16(15) . . . . ?
C13B C8B N2B C7B 107.54(15) . . . . ?
C9B C8B N2B C14B 167.11(14) . . . . ?
C12B C8B N2B C14B 48.54(19) . . . . ?
C13B C8B N2B C14B -79.76(18) . . . . ?
O2B C20B N3B C21B -0.7(3) . . . . ?
C17B C20B N3B C21B 178.61(15) . . . . ?
N5 C22 C23 N5 1.0(3) . . . 2_556 ?
C23 C22 N5 C23 -0.9(3) . . . 2_556 ?
