#------------------------------------------------------------------------------
#$Date: 2023-04-06 10:32:07 +0300 (Thu, 06 Apr 2023) $
#$Revision: 282460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107051.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_8107051
loop_
_publ_author_name
'Al-Alshaikh, Monirah A.'
'Ghabbour, Hazem A.'
'Abuelizz, Hatem A.'
'Alruqi, Obaid S.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-[(E)-(2,6-difluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione,
 C31H36F2N6S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              927
_journal_page_last               929
_journal_paper_doi               10.1515/ncrs-2016-0009
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C31 H36 F2 N6 S'
_chemical_formula_weight         562.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 95.888(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7561(8)
_cell_length_b                   24.6766(13)
_cell_length_c                   7.7811(4)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.89
_cell_measurement_theta_min      2.16
_cell_volume                     2818.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6468
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.758
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0516P)²+1.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4817
_reflns_number_total             6468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0009_suppl.cif
_cod_data_source_block           t
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107051
_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   0.926
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97668(5) 0.46948(2) 0.23439(8) 0.02047(16) Uani 1 1 d . . . . .
F1 F 0.74649(10) 0.30124(6) 0.5218(2) 0.0266(4) Uani 1 1 d . . . . .
F2 F 1.04001(10) 0.30416(6) 0.3347(2) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.84177(14) 0.45159(8) 0.4548(2) 0.0147(4) Uani 1 1 d . . . . .
N2 N 0.79924(14) 0.53516(8) 0.5099(2) 0.0155(4) Uani 1 1 d . . . . .
N3 N 0.86593(14) 0.53501(8) 0.3977(3) 0.0156(4) Uani 1 1 d . . . . .
N4 N 0.86437(14) 0.61665(8) 0.2129(3) 0.0160(4) Uani 1 1 d . . . . .
N5 N 0.73701(15) 0.64156(8) -0.0791(3) 0.0185(5) Uani 1 1 d . . . . .
N6 N 0.83721(14) 0.39557(8) 0.4738(3) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.71672(16) 0.46542(9) 0.6608(3) 0.0147(5) Uani 1 1 d . . . . .
C2 C 0.66778(17) 0.51537(9) 0.7275(3) 0.0168(5) Uani 1 1 d . . . . .
H2A H 0.7131 0.5400 0.7892 0.020 Uiso 1 1 calc R U . . .
H2B H 0.6362 0.5354 0.6286 0.020 Uiso 1 1 calc R U . . .
C3 C 0.59822(18) 0.49750(10) 0.8503(3) 0.0191(5) Uani 1 1 d . . . . .
H3A H 0.5672 0.5302 0.8927 0.023 Uiso 1 1 calc R U . . .
C4 C 0.64749(18) 0.46709(10) 1.0051(3) 0.0205(5) Uani 1 1 d . . . . .
H4A H 0.6931 0.4911 1.0684 0.025 Uiso 1 1 calc R U . . .
H4B H 0.6031 0.4559 1.0853 0.025 Uiso 1 1 calc R U . . .
C5 C 0.69487(18) 0.41699(10) 0.9387(3) 0.0189(5) Uani 1 1 d . . . . .
H5A H 0.7264 0.3968 1.0391 0.023 Uiso 1 1 calc R U . . .
C6 C 0.76539(17) 0.43475(9) 0.8181(3) 0.0165(5) Uani 1 1 d . . . . .
H6A H 0.7973 0.4026 0.7779 0.020 Uiso 1 1 calc R U . . .
H6B H 0.8112 0.4587 0.8813 0.020 Uiso 1 1 calc R U . . .
C7 C 0.52722(17) 0.46040(10) 0.7538(3) 0.0211(5) Uani 1 1 d . . . . .
H7A H 0.4945 0.4802 0.6555 0.025 Uiso 1 1 calc R U . . .
H7B H 0.4821 0.4489 0.8323 0.025 Uiso 1 1 calc R U . . .
C8 C 0.57500(17) 0.41062(10) 0.6874(3) 0.0180(5) Uani 1 1 d . . . . .
H8A H 0.5286 0.3863 0.6245 0.022 Uiso 1 1 calc R U . . .
C9 C 0.62426(18) 0.37990(10) 0.8408(3) 0.0200(5) Uani 1 1 d . . . . .
H9A H 0.5796 0.3677 0.9192 0.024 Uiso 1 1 calc R U . . .
H9B H 0.6548 0.3475 0.7988 0.024 Uiso 1 1 calc R U . . .
C10 C 0.64429(17) 0.42812(9) 0.5644(3) 0.0166(5) Uani 1 1 d . . . . .
H10A H 0.6127 0.4477 0.4644 0.020 Uiso 1 1 calc R U . . .
H10B H 0.6742 0.3957 0.5205 0.020 Uiso 1 1 calc R U . . .
C11 C 0.78471(16) 0.48445(9) 0.5424(3) 0.0141(5) Uani 1 1 d . . . . .
C12 C 0.89530(17) 0.48463(9) 0.3621(3) 0.0160(5) Uani 1 1 d . . . . .
C13 C 0.90839(17) 0.58716(9) 0.3568(3) 0.0172(5) Uani 1 1 d . . . . .
H13A H 0.9106 0.6106 0.4603 0.021 Uiso 1 1 calc R U . . .
H13B H 0.9721 0.5800 0.3340 0.021 Uiso 1 1 calc R U . . .
C14 C 0.86854(18) 0.58909(10) 0.0466(3) 0.0187(5) Uani 1 1 d . . . . .
H14A H 0.8324 0.5552 0.0441 0.022 Uiso 1 1 calc R U . . .
H14B H 0.9325 0.5794 0.0323 0.022 Uiso 1 1 calc R U . . .
C15 C 0.83131(17) 0.62573(10) -0.0992(3) 0.0201(5) Uani 1 1 d . . . . .
H15A H 0.8698 0.6586 -0.1006 0.024 Uiso 1 1 calc R U . . .
H15B H 0.8333 0.6067 -0.2108 0.024 Uiso 1 1 calc R U . . .
C16 C 0.73477(19) 0.66966(10) 0.0861(3) 0.0207(5) Uani 1 1 d . . . . .
H16A H 0.6715 0.6806 0.1007 0.025 Uiso 1 1 calc R U . . .
H16B H 0.7725 0.7028 0.0872 0.025 Uiso 1 1 calc R U . . .
C17 C 0.77057(18) 0.63294(10) 0.2335(3) 0.0189(5) Uani 1 1 d . . . . .
H17A H 0.7688 0.6522 0.3447 0.023 Uiso 1 1 calc R U . . .
H17B H 0.7315 0.6004 0.2350 0.023 Uiso 1 1 calc R U . . .
C18 C 0.70184(19) 0.67613(11) -0.2241(3) 0.0270(6) Uani 1 1 d . . . . .
H18A H 0.7074 0.6566 -0.3337 0.032 Uiso 1 1 calc R U . . .
H18B H 0.7396 0.7093 -0.2241 0.032 Uiso 1 1 calc R U . . .
C19 C 0.60367(19) 0.69217(10) -0.2166(3) 0.0212(6) Uani 1 1 d . . . . .
C20 C 0.5806(2) 0.74361(10) -0.1626(3) 0.0264(6) Uani 1 1 d . . . . .
H20A H 0.6273 0.7693 -0.1311 0.032 Uiso 1 1 calc R U . . .
C21 C 0.4907(2) 0.75797(11) -0.1542(3) 0.0298(7) Uani 1 1 d . . . . .
H21A H 0.4761 0.7933 -0.1174 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4222(2) 0.72115(11) -0.1990(3) 0.0272(6) Uani 1 1 d . . . . .
H22A H 0.3603 0.7313 -0.1953 0.033 Uiso 1 1 calc R U . . .
C23 C 0.4439(2) 0.66922(11) -0.2498(3) 0.0253(6) Uani 1 1 d . . . . .
H23A H 0.3970 0.6435 -0.2786 0.030 Uiso 1 1 calc R U . . .
C24 C 0.53408(19) 0.65506(10) -0.2583(3) 0.0235(6) Uani 1 1 d . . . . .
H24A H 0.5486 0.6195 -0.2933 0.028 Uiso 1 1 calc R U . . .
C25 C 0.89500(17) 0.36578(9) 0.4068(3) 0.0171(5) Uani 1 1 d . . . . .
H25A H 0.9396 0.3820 0.3436 0.021 Uiso 1 1 calc R U . . .
C26 C 0.89317(16) 0.30654(9) 0.4265(3) 0.0155(5) Uani 1 1 d . . . . .
C27 C 0.82227(17) 0.27572(10) 0.4794(3) 0.0178(5) Uani 1 1 d . . . . .
C28 C 0.82366(18) 0.21974(10) 0.4874(3) 0.0227(6) Uani 1 1 d . . . . .
H28A H 0.7731 0.2002 0.5223 0.027 Uiso 1 1 calc R U . . .
C29 C 0.90022(18) 0.19275(10) 0.4437(3) 0.0214(6) Uani 1 1 d . . . . .
H29A H 0.9025 0.1543 0.4505 0.026 Uiso 1 1 calc R U . . .
C30 C 0.97328(18) 0.22065(10) 0.3903(3) 0.0205(6) Uani 1 1 d . . . . .
H30A H 1.0255 0.2021 0.3587 0.025 Uiso 1 1 calc R U . . .
C31 C 0.96806(17) 0.27621(10) 0.3845(3) 0.0180(5) 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'
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
C12 N1 N6 132.40(19) . .
C12 N1 C11 108.46(19) . .
N6 N1 C11 119.13(19) . .
C11 N2 N3 105.25(18) . .
C12 N3 N2 113.29(18) . .
C12 N3 C13 127.1(2) . .
N2 N3 C13 118.57(18) . .
C13 N4 C17 114.25(19) . .
C13 N4 C14 113.36(19) . .
C17 N4 C14 110.42(19) . .
C16 N5 C18 111.2(2) . .
C16 N5 C15 109.1(2) . .
C18 N5 C15 109.7(2) . .
C25 N6 N1 119.1(2) . .
C11 C1 C10 111.09(19) . .
C11 C1 C2 108.71(18) . .
C10 C1 C2 108.34(19) . .
C11 C1 C6 110.58(19) . .
C10 C1 C6 109.49(19) . .
C2 C1 C6 108.57(18) . .
C3 C2 C1 110.18(19) . .
C3 C2 H2A 109.6 . .
C1 C2 H2A 109.6 . .
C3 C2 H2B 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
C7 C3 C2 109.5(2) . .
C7 C3 C4 109.7(2) . .
C2 C3 C4 109.6(2) . .
C7 C3 H3A 109.3 . .
C2 C3 H3A 109.3 . .
C4 C3 H3A 109.3 . .
C5 C4 C3 108.94(19) . .
C5 C4 H4A 109.9 . .
C3 C4 H4A 109.9 . .
C5 C4 H4B 109.9 . .
C3 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
C9 C5 C6 109.67(19) . .
C9 C5 C4 109.8(2) . .
C6 C5 C4 109.66(19) . .
C9 C5 H5A 109.2 . .
C6 C5 H5A 109.2 . .
C4 C5 H5A 109.2 . .
C5 C6 C1 109.48(19) . .
C5 C6 H6A 109.8 . .
C1 C6 H6A 109.8 . .
C5 C6 H6B 109.8 . .
C1 C6 H6B 109.8 . .
H6A C6 H6B 108.2 . .
C3 C7 C8 109.3(2) . .
C3 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
C3 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.3 . .
C7 C8 C9 109.4(2) . .
C7 C8 C10 110.15(19) . .
C9 C8 C10 109.4(2) . .
C7 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
C10 C8 H8A 109.3 . .
C5 C9 C8 109.6(2) . .
C5 C9 H9A 109.7 . .
C8 C9 H9A 109.7 . .
C5 C9 H9B 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
C8 C10 C1 109.70(19) . .
C8 C10 H10A 109.7 . .
C1 C10 H10A 109.7 . .
C8 C10 H10B 109.7 . .
C1 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
N2 C11 N1 110.2(2) . .
N2 C11 C1 123.6(2) . .
N1 C11 C1 126.2(2) . .
N3 C12 N1 102.81(19) . .
N3 C12 S1 126.09(18) . .
N1 C12 S1 131.10(18) . .
N4 C13 N3 116.2(2) . .
N4 C13 H13A 108.2 . .
N3 C13 H13A 108.2 . .
N4 C13 H13B 108.2 . .
N3 C13 H13B 108.2 . .
H13A C13 H13B 107.4 . .
N4 C14 C15 109.87(19) . .
N4 C14 H14A 109.7 . .
C15 C14 H14A 109.7 . .
N4 C14 H14B 109.7 . .
C15 C14 H14B 109.7 . .
H14A C14 H14B 108.2 . .
N5 C15 C14 110.8(2) . .
N5 C15 H15A 109.5 . .
C14 C15 H15A 109.5 . .
N5 C15 H15B 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 108.1 . .
N5 C16 C17 110.13(19) . .
N5 C16 H16A 109.6 . .
C17 C16 H16A 109.6 . .
N5 C16 H16B 109.6 . .
C17 C16 H16B 109.6 . .
H16A C16 H16B 108.1 . .
N4 C17 C16 110.0(2) . .
N4 C17 H17A 109.7 . .
C16 C17 H17A 109.7 . .
N4 C17 H17B 109.7 . .
C16 C17 H17B 109.7 . .
H17A C17 H17B 108.2 . .
N5 C18 C19 112.8(2) . .
N5 C18 H18A 109.0 . .
C19 C18 H18A 109.0 . .
N5 C18 H18B 109.0 . .
C19 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C24 C19 C20 118.3(3) . .
C24 C19 C18 120.5(2) . .
C20 C19 C18 121.2(3) . .
C21 C20 C19 121.0(3) . .
C21 C20 H20A 119.5 . .
C19 C20 H20A 119.5 . .
C22 C21 C20 120.1(2) . .
C22 C21 H21A 119.9 . .
C20 C21 H21A 119.9 . .
C21 C22 C23 119.8(3) . .
C21 C22 H22A 120.1 . .
C23 C22 H22A 120.1 . .
C24 C23 C22 119.9(3) . .
C24 C23 H23A 120.1 . .
C22 C23 H23A 120.1 . .
C23 C24 C19 120.9(2) . .
C23 C24 H24A 119.6 . .
C19 C24 H24A 119.6 . .
N6 C25 C26 120.6(2) . .
N6 C25 H25A 119.7 . .
C26 C25 H25A 119.7 . .
C27 C26 C31 114.4(2) . .
C27 C26 C25 126.7(2) . .
C31 C26 C25 118.9(2) . .
F1 C27 C28 117.5(2) . .
F1 C27 C26 118.9(2) . .
C28 C27 C26 123.5(2) . .
C27 C28 C29 118.6(2) . .
C27 C28 H28A 120.7 . .
C29 C28 H28A 120.7 . .
C30 C29 C28 121.1(2) . .
C30 C29 H29A 119.4 . .
C28 C29 H29A 119.4 . .
C31 C30 C29 117.8(2) . .
C31 C30 H30A 121.1 . .
C29 C30 H30A 121.1 . .
F2 C31 C30 118.3(2) . .
F2 C31 C26 117.0(2) . .
C30 C31 C26 124.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C12 1.677(2) .
F1 C27 1.353(3) .
F2 C31 1.355(3) .
N1 C12 1.388(3) .
N1 N6 1.393(3) .
N1 C11 1.396(3) .
N2 C11 1.299(3) .
N2 N3 1.381(3) .
N3 C12 1.355(3) .
N3 C13 1.480(3) .
N4 C13 1.434(3) .
N4 C17 1.466(3) .
N4 C14 1.468(3) .
N5 C16 1.464(3) .
N5 C18 1.467(3) .
N5 C15 1.469(3) .
N6 C25 1.277(3) .
C1 C11 1.505(3) .
C1 C10 1.545(3) .
C1 C2 1.545(3) .
C1 C6 1.552(3) .
C2 C3 1.537(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C7 1.529(4) .
C3 C4 1.537(3) .
C3 H3A 1.0000 .
C4 C5 1.536(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C9 1.530(4) .
C5 C6 1.535(3) .
C5 H5A 1.0000 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.532(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.533(3) .
C8 C10 1.533(3) .
C8 H8A 1.0000 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.510(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.513(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.509(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C24 1.389(4) .
C19 C20 1.390(4) .
C20 C21 1.381(4) .
C20 H20A 0.9500 .
C21 C22 1.377(4) .
C21 H21A 0.9500 .
C22 C23 1.388(4) .
C22 H22A 0.9500 .
C23 C24 1.384(4) .
C23 H23A 0.9500 .
C24 H24A 0.9500 .
C25 C26 1.470(3) .
C25 H25A 0.9500 .
C26 C27 1.389(3) .
C26 C31 1.401(3) .
C27 C28 1.383(3) .
C28 C29 1.384(4) .
C28 H28A 0.9500 .
C29 C30 1.379(4) .
C29 H29A 0.9500 .
C30 C31 1.374(3) .
C30 H30A 0.9500 .
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
C11 N2 N3 C12 -1.5(3) . . . .
C11 N2 N3 C13 -170.5(2) . . . .
C12 N1 N6 C25 5.7(4) . . . .
C11 N1 N6 C25 -173.6(2) . . . .
C11 C1 C2 C3 -179.5(2) . . . .
C10 C1 C2 C3 59.6(2) . . . .
C6 C1 C2 C3 -59.2(3) . . . .
C1 C2 C3 C7 -60.3(3) . . . .
C1 C2 C3 C4 60.1(3) . . . .
C7 C3 C4 C5 60.1(3) . . . .
C2 C3 C4 C5 -60.2(3) . . . .
C3 C4 C5 C9 -59.5(3) . . . .
C3 C4 C5 C6 61.0(3) . . . .
C9 C5 C6 C1 59.6(2) . . . .
C4 C5 C6 C1 -61.1(3) . . . .
C11 C1 C6 C5 178.69(19) . . . .
C10 C1 C6 C5 -58.6(2) . . . .
C2 C1 C6 C5 59.5(2) . . . .
C2 C3 C7 C8 59.6(3) . . . .
C4 C3 C7 C8 -60.7(2) . . . .
C3 C7 C8 C9 60.3(3) . . . .
C3 C7 C8 C10 -60.0(3) . . . .
C6 C5 C9 C8 -60.8(3) . . . .
C4 C5 C9 C8 59.8(3) . . . .
C7 C8 C9 C5 -59.9(3) . . . .
C10 C8 C9 C5 60.8(2) . . . .
C7 C8 C10 C1 60.3(3) . . . .
C9 C8 C10 C1 -60.0(2) . . . .
C11 C1 C10 C8 -178.66(19) . . . .
C2 C1 C10 C8 -59.3(2) . . . .
C6 C1 C10 C8 58.9(2) . . . .
N3 N2 C11 N1 0.8(3) . . . .
N3 N2 C11 C1 179.8(2) . . . .
C12 N1 C11 N2 0.1(3) . . . .
N6 N1 C11 N2 179.5(2) . . . .
C12 N1 C11 C1 -178.8(2) . . . .
N6 N1 C11 C1 0.6(3) . . . .
C10 C1 C11 N2 121.0(2) . . . .
C2 C1 C11 N2 1.9(3) . . . .
C6 C1 C11 N2 -117.2(2) . . . .
C10 C1 C11 N1 -60.2(3) . . . .
C2 C1 C11 N1 -179.3(2) . . . .
C6 C1 C11 N1 61.6(3) . . . .
N2 N3 C12 N1 1.5(3) . . . .
C13 N3 C12 N1 169.4(2) . . . .
N2 N3 C12 S1 -178.80(18) . . . .
C13 N3 C12 S1 -10.9(4) . . . .
N6 N1 C12 N3 179.7(2) . . . .
C11 N1 C12 N3 -0.9(2) . . . .
N6 N1 C12 S1 0.0(4) . . . .
C11 N1 C12 S1 179.4(2) . . . .
C17 N4 C13 N3 61.4(3) . . . .
C14 N4 C13 N3 -66.3(3) . . . .
C12 N3 C13 N4 103.6(3) . . . .
N2 N3 C13 N4 -89.0(3) . . . .
C13 N4 C14 C15 -173.0(2) . . . .
C17 N4 C14 C15 57.4(3) . . . .
C16 N5 C15 C14 59.2(3) . . . .
C18 N5 C15 C14 -178.8(2) . . . .
N4 C14 C15 N5 -58.2(3) . . . .
C18 N5 C16 C17 179.5(2) . . . .
C15 N5 C16 C17 -59.4(3) . . . .
C13 N4 C17 C16 172.79(19) . . . .
C14 N4 C17 C16 -58.0(3) . . . .
N5 C16 C17 N4 59.3(3) . . . .
C16 N5 C18 C19 -61.7(3) . . . .
C15 N5 C18 C19 177.6(2) . . . .
N5 C18 C19 C24 -75.0(3) . . . .
N5 C18 C19 C20 102.9(3) . . . .
C24 C19 C20 C21 -1.4(4) . . . .
C18 C19 C20 C21 -179.3(2) . . . .
C19 C20 C21 C22 0.2(4) . . . .
C20 C21 C22 C23 1.2(4) . . . .
C21 C22 C23 C24 -1.3(4) . . . .
C22 C23 C24 C19 0.1(4) . . . .
C20 C19 C24 C23 1.2(4) . . . .
C18 C19 C24 C23 179.2(2) . . . .
N1 N6 C25 C26 179.0(2) . . . .
N6 C25 C26 C27 15.5(4) . . . .
N6 C25 C26 C31 -166.5(2) . . . .
C31 C26 C27 F1 -179.6(2) . . . .
C25 C26 C27 F1 -1.5(4) . . . .
C31 C26 C27 C28 -1.1(4) . . . .
C25 C26 C27 C28 176.9(2) . . . .
F1 C27 C28 C29 179.6(2) . . . .
C26 C27 C28 C29 1.2(4) . . . .
C27 C28 C29 C30 -1.0(4) . . . .
C28 C29 C30 C31 0.9(4) . . . .
C29 C30 C31 F2 179.0(2) . . . .
C29 C30 C31 C26 -0.9(4) . . . .
C27 C26 C31 F2 -178.9(2) . . . .
C25 C26 C31 F2 2.8(3) . . . .
C27 C26 C31 C30 1.0(4) . . . .
C25 C26 C31 C30 -177.2(2) . . . .
