#------------------------------------------------------------------------------
#$Date: 2024-06-13 00:40:26 +0200 (Thu 13 de Jun de 2024) $
#$Revision: 292325 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/88/7248830.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_7248830
loop_
_publ_author_name
'Prashanth, Jupally'
'Voronin, Alexander P.'
'Surov, Artem'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Design of Pyrazine Cocrystals of Enzalutamide --a lead from 1, 4-dioxane
 Solvates
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00566J
_journal_year                    2024
_chemical_formula_moiety         'C21 H16 F4 N4 O2 S, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C23 H20 F4 N4 O3 S'
_chemical_formula_weight         508.49
_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                91.249(3)
_cell_angle_beta                 100.527(3)
_cell_angle_gamma                93.264(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3391(10)
_cell_length_b                   9.0572(10)
_cell_length_c                   15.2669(17)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.49
_cell_volume                     1131.2(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25460
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.567
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6675
_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    1.493
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6856
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0357
_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)+(0.0381P)²+0.5521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5678
_reflns_number_total             6856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00566j2.cif
_cod_data_source_block           KB435_0m
_cod_database_code               7248830
_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   0.963
_shelx_estimated_absorpt_t_max   0.983
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
C1 C 0.39703(13) 0.00248(12) 0.12794(7) 0.0124(2) Uani 1 1 d . . . . .
C2 C 0.53232(14) -0.04531(13) 0.18534(7) 0.0141(2) Uani 1 1 d . . . . .
H2 H 0.568648 0.002757 0.242010 0.017 Uiso 1 1 calc R U . . .
C3 C 0.61378(13) -0.16327(13) 0.15949(7) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.55850(14) -0.23556(12) 0.07649(7) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.41880(14) -0.18982(13) 0.02122(7) 0.0145(2) Uani 1 1 d . . . . .
H5 H 0.378765 -0.240666 -0.034230 0.017 Uiso 1 1 calc R U . . .
C6 C 0.33804(14) -0.07094(13) 0.04652(7) 0.0138(2) Uani 1 1 d . . . . .
H6 H 0.243345 -0.039967 0.008616 0.017 Uiso 1 1 calc R U . . .
C7 C 0.38666(13) 0.25936(12) 0.19315(7) 0.0125(2) Uani 1 1 d . . . . .
C8 C 0.10105(13) 0.26262(12) 0.18690(8) 0.0141(2) Uani 1 1 d . . . . .
C9 C 0.14450(14) 0.11698(13) 0.14921(7) 0.0138(2) Uani 1 1 d . . . . .
C10 C 0.75153(15) -0.21604(14) 0.22645(9) 0.0196(2) Uani 1 1 d D U . . .
C11 C 0.64240(15) -0.35288(13) 0.04216(8) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.02816(16) 0.23620(14) 0.27057(9) 0.0209(2) Uani 1 1 d . . . . .
H12A H -0.072646 0.172631 0.255058 0.031 Uiso 1 1 calc R U . . .
H12B H 0.003644 0.331152 0.295496 0.031 Uiso 1 1 calc R U . . .
H12C H 0.106766 0.187886 0.314765 0.031 Uiso 1 1 calc R U . . .
C13 C -0.01677(15) 0.33744(14) 0.11551(9) 0.0209(2) Uani 1 1 d . . . . .
H13A H 0.038322 0.363098 0.065935 0.031 Uiso 1 1 calc R U . . .
H13B H -0.052014 0.427564 0.141076 0.031 Uiso 1 1 calc R U . . .
H13C H -0.112286 0.269698 0.093663 0.031 Uiso 1 1 calc R U . . .
C14 C 0.28903(13) 0.48402(12) 0.25272(7) 0.0123(2) Uani 1 1 d . . . . .
C15 C 0.36592(14) 0.49772(13) 0.34163(7) 0.0136(2) Uani 1 1 d . . . . .
H15 H 0.409947 0.414979 0.372539 0.016 Uiso 1 1 calc R U . . .
C16 C 0.37617(14) 0.63548(13) 0.38350(7) 0.0137(2) Uani 1 1 d . . . . .
C17 C 0.31007(14) 0.75924(12) 0.34200(7) 0.0136(2) Uani 1 1 d . . . . .
C18 C 0.23882(14) 0.74192(13) 0.25214(7) 0.0146(2) Uani 1 1 d . . . . .
H18 H 0.195860 0.825024 0.221186 0.018 Uiso 1 1 calc R U . . .
C19 C 0.22902(14) 0.60650(13) 0.20676(7) 0.0144(2) Uani 1 1 d . . . . .
H19 H 0.182060 0.597321 0.145176 0.017 Uiso 1 1 calc R U . . .
C20 C 0.30984(14) 0.90861(13) 0.38682(8) 0.0157(2) Uani 1 1 d . . . . .
C21 C 0.26066(19) 1.04353(15) 0.51862(9) 0.0264(3) Uani 1 1 d . . . . .
H21A H 0.335536 1.120966 0.502136 0.040 Uiso 1 1 calc R U . . .
H21B H 0.290178 1.026514 0.582560 0.040 Uiso 1 1 calc R U . . .
H21C H 0.148476 1.074817 0.504965 0.040 Uiso 1 1 calc R U . . .
N1 N 0.31332(11) 0.12426(10) 0.15385(6) 0.01248(18) Uani 1 1 d . . . . .
N2 N 0.26469(11) 0.34124(10) 0.20916(6) 0.01266(18) Uani 1 1 d . . . . .
N3 N 0.27217(14) 0.90772(12) 0.46855(7) 0.0196(2) Uani 1 1 d . . . . .
H3N H 0.248(2) 0.824(2) 0.4892(12) 0.029 Uiso 1 1 d . U . . .
N4 N 0.70642(14) -0.44261(13) 0.00979(7) 0.0225(2) Uani 1 1 d . . . . .
O1 O 0.05065(10) 0.01332(10) 0.12040(6) 0.01861(18) Uani 1 1 d . . . . .
O2 O 0.33749(12) 1.02229(10) 0.34804(6) 0.02242(19) Uani 1 1 d . . . . .
F1 F 0.84036(10) -0.10628(9) 0.27439(5) 0.02552(18) Uani 1 1 d . . . . .
F4 F 0.45455(9) 0.64906(8) 0.46961(5) 0.01911(15) Uani 1 1 d . . . . .
S1 S 0.58361(3) 0.30994(3) 0.21175(2) 0.01638(7) Uani 1 1 d . . . . .
F2 F 0.8418(8) -0.3134(7) 0.1988(3) 0.0348(10) Uani 0.555(18) 1 d D U P A 1
F3 F 0.6874(5) -0.2849(7) 0.2947(3) 0.0293(8) Uani 0.555(18) 1 d D U P A 1
F2D F 0.8697(6) -0.2667(11) 0.1815(5) 0.0368(13) Uani 0.445(18) 1 d D U P A 2
F3D F 0.7064(10) -0.3236(9) 0.2712(7) 0.0456(16) Uani 0.445(18) 1 d D U P A 2
C22 C -0.01745(15) 0.60289(14) 0.43291(8) 0.0195(2) Uani 1 1 d . . . . .
H22A H 0.031415 0.553218 0.386623 0.023 Uiso 1 1 calc R U . . .
H22B H -0.056846 0.698014 0.409553 0.023 Uiso 1 1 calc R U . . .
C23 C -0.15947(15) 0.50667(15) 0.45258(9) 0.0211(2) Uani 1 1 d . . . . .
H23A H -0.212823 0.558933 0.496027 0.025 Uiso 1 1 calc R U . . .
H23B H -0.241025 0.486895 0.397140 0.025 Uiso 1 1 calc R U . . .
O3 O 0.10421(11) 0.63064(10) 0.51181(6) 0.01982(18) 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
C6 C1 C2 120.76(10) . . ?
C6 C1 N1 119.14(10) . . ?
C2 C1 N1 120.05(10) . . ?
C3 C2 C1 119.74(10) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.06(10) . . ?
C2 C3 C10 117.25(10) . . ?
C4 C3 C10 122.49(10) . . ?
C5 C4 C3 119.40(10) . . ?
C5 C4 C11 117.07(10) . . ?
C3 C4 C11 123.47(10) . . ?
C6 C5 C4 120.63(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.32(10) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2 C7 N1 106.72(9) . . ?
N2 C7 S1 126.80(9) . . ?
N1 C7 S1 126.43(8) . . ?
N2 C8 C9 100.59(9) . . ?
N2 C8 C13 113.37(10) . . ?
C9 C8 C13 109.28(10) . . ?
N2 C8 C12 111.26(9) . . ?
C9 C8 C12 110.05(10) . . ?
C13 C8 C12 111.71(10) . . ?
O1 C9 N1 126.04(11) . . ?
O1 C9 C8 126.54(10) . . ?
N1 C9 C8 107.41(9) . . ?
F3D C10 F1 115.4(4) . . ?
F2 C10 F1 112.2(3) . . ?
F3D C10 F2D 107.2(3) . . ?
F1 C10 F2D 98.8(3) . . ?
F2 C10 F3 104.7(2) . . ?
F1 C10 F3 98.7(3) . . ?
F3D C10 C3 112.7(3) . . ?
F2 C10 C3 117.3(2) . . ?
F1 C10 C3 112.87(10) . . ?
F2D C10 C3 108.7(3) . . ?
F3 C10 C3 108.97(19) . . ?
N4 C11 C4 175.80(13) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.96(10) . . ?
C15 C14 N2 119.44(10) . . ?
C19 C14 N2 119.53(10) . . ?
C16 C15 C14 117.83(10) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
F4 C16 C15 117.62(10) . . ?
F4 C16 C17 119.02(10) . . ?
C15 C16 C17 123.36(10) . . ?
C16 C17 C18 116.94(10) . . ?
C16 C17 C20 124.93(10) . . ?
C18 C17 C20 118.13(10) . . ?
C19 C18 C17 121.68(10) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 119.09(10) . . ?
C18 C19 H19 120.5 . . ?
C14 C19 H19 120.5 . . ?
O2 C20 N3 123.71(11) . . ?
O2 C20 C17 120.67(10) . . ?
N3 C20 C17 115.59(10) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 N1 C7 111.49(9) . . ?
C9 N1 C1 122.34(9) . . ?
C7 N1 C1 125.97(9) . . ?
C7 N2 C14 124.12(9) . . ?
C7 N2 C8 113.66(9) . . ?
C14 N2 C8 121.87(9) . . ?
C20 N3 C21 121.89(11) . . ?
C20 N3 H3N 117.5(12) . . ?
C21 N3 H3N 120.4(12) . . ?
O3 C22 C23 110.73(10) . . ?
O3 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O3 C23 C22 110.31(10) 2_566 . ?
O3 C23 H23A 109.6 2_566 . ?
C22 C23 H23A 109.6 . . ?
O3 C23 H23B 109.6 2_566 . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C22 O3 C23 109.98(9) . 2_566 ?
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 C6 1.3902(15) . ?
C1 C2 1.3925(15) . ?
C1 N1 1.4248(14) . ?
C2 C3 1.3860(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4011(16) . ?
C3 C10 1.4993(16) . ?
C4 C5 1.3971(16) . ?
C4 C11 1.4449(16) . ?
C5 C6 1.3862(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.3465(14) . ?
C7 N1 1.4071(14) . ?
C7 S1 1.6511(12) . ?
C8 N2 1.4812(14) . ?
C8 C9 1.5166(16) . ?
C8 C13 1.5263(16) . ?
C8 C12 1.5293(17) . ?
C9 O1 1.2082(14) . ?
C9 N1 1.3943(14) . ?
C10 F3D 1.280(5) . ?
C10 F2 1.303(4) . ?
C10 F1 1.3263(14) . ?
C10 F2D 1.392(5) . ?
C10 F3 1.399(4) . ?
C11 N4 1.1480(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3909(15) . ?
C14 C19 1.3937(15) . ?
C14 N2 1.4279(14) . ?
C15 C16 1.3805(16) . ?
C15 H15 0.9500 . ?
C16 F4 1.3566(12) . ?
C16 C17 1.3912(16) . ?
C17 C18 1.3936(15) . ?
C17 C20 1.5030(16) . ?
C18 C19 1.3863(16) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O2 1.2301(14) . ?
C20 N3 1.3414(15) . ?
C21 N3 1.4511(16) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N3 H3N 0.857(18) . ?
C22 O3 1.4334(15) . ?
C22 C23 1.5087(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O3 1.4345(15) 2_566 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
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 H3N O3 0.857(18) 2.135(19) 2.9505(14) 158.7(17) . yes
C5 H5 S1 0.95 2.85 3.6930(12) 149.1 2_655 yes
C12 H12C O2 0.98 2.49 3.3706(17) 149.0 1_545 yes
C18 H18 O1 0.95 2.53 3.4715(15) 170.0 1_565 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
C6 C1 C2 C3 2.92(17) . . . . ?
N1 C1 C2 C3 -179.61(10) . . . . ?
C1 C2 C3 C4 -1.02(17) . . . . ?
C1 C2 C3 C10 -176.04(11) . . . . ?
C2 C3 C4 C5 -1.46(17) . . . . ?
C10 C3 C4 C5 173.28(11) . . . . ?
C2 C3 C4 C11 175.84(11) . . . . ?
C10 C3 C4 C11 -9.41(18) . . . . ?
C3 C4 C5 C6 2.12(17) . . . . ?
C11 C4 C5 C6 -175.36(11) . . . . ?
C4 C5 C6 C1 -0.26(17) . . . . ?
C2 C1 C6 C5 -2.27(17) . . . . ?
N1 C1 C6 C5 -179.77(10) . . . . ?
N2 C8 C9 O1 -179.42(11) . . . . ?
C13 C8 C9 O1 -59.88(15) . . . . ?
C12 C8 C9 O1 63.14(15) . . . . ?
N2 C8 C9 N1 0.60(11) . . . . ?
C13 C8 C9 N1 120.14(10) . . . . ?
C12 C8 C9 N1 -116.84(10) . . . . ?
C2 C3 C10 F3D 94.4(7) . . . . ?
C4 C3 C10 F3D -80.4(7) . . . . ?
C2 C3 C10 F2 -171.2(5) . . . . ?
C4 C3 C10 F2 13.9(5) . . . . ?
C2 C3 C10 F1 -38.40(15) . . . . ?
C4 C3 C10 F1 146.71(11) . . . . ?
C2 C3 C10 F2D -146.9(4) . . . . ?
C4 C3 C10 F2D 38.2(5) . . . . ?
C2 C3 C10 F3 70.1(3) . . . . ?
C4 C3 C10 F3 -104.8(3) . . . . ?
C19 C14 C15 C16 2.00(17) . . . . ?
N2 C14 C15 C16 -175.13(10) . . . . ?
C14 C15 C16 F4 -178.53(10) . . . . ?
C14 C15 C16 C17 1.71(17) . . . . ?
F4 C16 C17 C18 176.50(10) . . . . ?
C15 C16 C17 C18 -3.75(17) . . . . ?
F4 C16 C17 C20 -3.61(17) . . . . ?
C15 C16 C17 C20 176.14(11) . . . . ?
C16 C17 C18 C19 2.15(17) . . . . ?
C20 C17 C18 C19 -177.74(11) . . . . ?
C17 C18 C19 C14 1.33(17) . . . . ?
C15 C14 C19 C18 -3.48(17) . . . . ?
N2 C14 C19 C18 173.65(10) . . . . ?
C16 C17 C20 O2 139.36(13) . . . . ?
C18 C17 C20 O2 -40.76(16) . . . . ?
C16 C17 C20 N3 -42.98(16) . . . . ?
C18 C17 C20 N3 136.91(12) . . . . ?
O1 C9 N1 C7 -178.45(11) . . . . ?
C8 C9 N1 C7 1.53(12) . . . . ?
O1 C9 N1 C1 -3.21(18) . . . . ?
C8 C9 N1 C1 176.78(9) . . . . ?
N2 C7 N1 C9 -3.23(12) . . . . ?
S1 C7 N1 C9 179.23(8) . . . . ?
N2 C7 N1 C1 -178.26(10) . . . . ?
S1 C7 N1 C1 4.19(16) . . . . ?
C6 C1 N1 C9 48.62(15) . . . . ?
C2 C1 N1 C9 -128.89(12) . . . . ?
C6 C1 N1 C7 -136.85(11) . . . . ?
C2 C1 N1 C7 45.64(16) . . . . ?
N1 C7 N2 C14 176.93(9) . . . . ?
S1 C7 N2 C14 -5.54(16) . . . . ?
N1 C7 N2 C8 3.72(12) . . . . ?
S1 C7 N2 C8 -178.74(8) . . . . ?
C15 C14 N2 C7 -65.33(15) . . . . ?
C19 C14 N2 C7 117.49(12) . . . . ?
C15 C14 N2 C8 107.34(12) . . . . ?
C19 C14 N2 C8 -69.84(14) . . . . ?
C9 C8 N2 C7 -2.71(12) . . . . ?
C13 C8 N2 C7 -119.25(11) . . . . ?
C12 C8 N2 C7 113.84(11) . . . . ?
C9 C8 N2 C14 -176.09(9) . . . . ?
C13 C8 N2 C14 67.37(13) . . . . ?
C12 C8 N2 C14 -59.54(13) . . . . ?
O2 C20 N3 C21 0.1(2) . . . . ?
C17 C20 N3 C21 -177.51(11) . . . . ?
O3 C22 C23 O3 -58.02(15) . . . 2_566 ?
C23 C22 O3 C23 57.83(15) . . . 2_566 ?
