#------------------------------------------------------------------------------
#$Date: 2022-05-20 12:46:42 +0300 (Fri, 20 May 2022) $
#$Revision: 275579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105323.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_8105323
loop_
_publ_author_name
'Alotaibi, Abdullah A.'
'Abdel-Wahab, Bakr F.'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
'El-Hiti, Gamal A.'
_publ_section_title
;
 The crystal structure of
 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole,
 C25H17BrFN3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              897
_journal_page_last               899
_journal_paper_doi               10.1515/ncrs-2020-0088
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C25 H17 Br F N3 S'
_chemical_formula_sum            'C25 H17 Br F N3 S'
_chemical_formula_weight         490.38
_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   geom
_cell_angle_alpha                109.211(4)
_cell_angle_beta                 90.211(4)
_cell_angle_gamma                95.290(4)
_cell_formula_units_Z            4
_cell_length_a                   11.2926(6)
_cell_length_b                   11.5832(4)
_cell_length_c                   16.9974(9)
_cell_measurement_reflns_used    4516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.8030
_cell_measurement_theta_min      3.2090
_cell_volume                     2089.21(18)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'WinGX and ORTEP [4]'
_computing_publication_material  'WinGX and ORTEP [4]'
_computing_structure_refinement  'SHELXL-2018 [3]'
_computing_structure_solution    'SHELXS [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18184
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.827
_diffrn_reflns_theta_min         2.175
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.826
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0580
_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)+(0.0745P)²+1.8505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5689
_reflns_number_total             9828
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0088_suppl.cif
_cod_data_source_block           bmk1723
_cod_database_code               8105323
_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   0.566
_shelx_estimated_absorpt_t_max   0.908
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 0.7847(3) -0.9138(3) -0.0235(3) 0.0449(9) Uani 1 1 d . . . . .
C2 C 0.7956(4) -0.8662(3) 0.0605(3) 0.0496(10) Uani 1 1 d . . . . .
C3 C 0.8437(4) -0.9531(4) 0.0985(3) 0.0579(11) Uani 1 1 d . . . . .
H3A H 0.788957 -0.972712 0.137200 0.070 Uiso 1 1 calc R U . . .
H3B H 0.920423 -0.920470 0.126766 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8542(3) -1.0631(3) 0.0213(3) 0.0520(10) Uani 1 1 d . . . . .
C5 C 0.8177(3) -1.0398(3) -0.0506(3) 0.0474(9) Uani 1 1 d . . . . .
C6 C 0.8937(4) -1.1753(4) 0.0138(4) 0.0643(13) Uani 1 1 d . . . . .
H6 H 0.919225 -1.191634 0.060814 0.077 Uiso 1 1 calc R U . . .
C7 C 0.8949(4) -1.2640(4) -0.0648(4) 0.0711(15) Uani 1 1 d . . . . .
H7 H 0.922093 -1.339470 -0.070144 0.085 Uiso 1 1 calc R U . . .
C8 C 0.8570(4) -1.2415(4) -0.1334(4) 0.0684(13) Uani 1 1 d . . . . .
H8 H 0.857739 -1.302330 -0.185239 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8165(4) -1.1285(4) -0.1280(3) 0.0589(11) Uani 1 1 d . . . . .
H9 H 0.789733 -1.113843 -0.175317 0.071 Uiso 1 1 calc R U . . .
C10 C 0.7353(3) -0.7322(3) -0.0106(3) 0.0449(9) Uani 1 1 d . . . . .
C11 C 0.6999(3) -0.6294(3) -0.1168(2) 0.0426(9) Uani 1 1 d . . . . .
H11 H 0.651597 -0.700770 -0.154705 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6363(3) -0.5129(3) -0.1024(3) 0.0450(9) Uani 1 1 d . . . . .
H12A H 0.674895 -0.460110 -0.130728 0.054 Uiso 1 1 calc R U . . .
H12B H 0.553341 -0.532903 -0.121040 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6487(3) -0.4542(3) -0.0097(2) 0.0414(8) Uani 1 1 d . . . . .
C14 C 0.8228(3) -0.6187(3) -0.1503(2) 0.0397(8) Uani 1 1 d . . . . .
C15 C 0.9256(3) -0.6046(3) -0.1016(3) 0.0448(9) Uani 1 1 d . . . . .
H15 H 0.919675 -0.603527 -0.046835 0.054 Uiso 1 1 calc R U . . .
C16 C 1.0366(4) -0.5920(3) -0.1335(3) 0.0524(10) Uani 1 1 d . . . . .
H16 H 1.105346 -0.581839 -0.100666 0.063 Uiso 1 1 calc R U . . .
C17 C 1.0431(4) -0.5949(4) -0.2139(3) 0.0565(11) Uani 1 1 d . . . . .
C18 C 0.9436(4) -0.6092(4) -0.2647(3) 0.0587(11) Uani 1 1 d . . . . .
H18 H 0.950311 -0.611258 -0.319593 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8335(4) -0.6205(4) -0.2313(3) 0.0515(10) Uani 1 1 d . . . . .
H19 H 0.765123 -0.629463 -0.264292 0.062 Uiso 1 1 calc R U . . .
C20 C 0.6190(3) -0.3308(3) 0.0363(3) 0.0414(8) Uani 1 1 d . . . . .
C21 C 0.5708(3) -0.2606(3) -0.0061(3) 0.0488(9) Uani 1 1 d . . . . .
H21 H 0.560032 -0.292225 -0.063754 0.059 Uiso 1 1 calc R U . . .
C22 C 0.5388(4) -0.1444(4) 0.0365(3) 0.0543(11) Uani 1 1 d . . . . .
H22 H 0.506645 -0.098061 0.007864 0.065 Uiso 1 1 calc R U . . .
C23 C 0.5551(4) -0.0989(3) 0.1210(3) 0.0527(10) Uani 1 1 d . . . . .
C24 C 0.6058(4) -0.1638(4) 0.1653(3) 0.0557(10) Uani 1 1 d . . . . .
H24 H 0.618604 -0.130090 0.222721 0.067 Uiso 1 1 calc R U . . .
C25 C 0.6370(4) -0.2798(4) 0.1224(3) 0.0513(10) Uani 1 1 d . . . . .
H25 H 0.670611 -0.324748 0.151575 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7911(4) -0.6370(4) -0.4978(3) 0.0595(11) Uani 1 1 d . . . . .
C27 C 0.7786(4) -0.6799(4) -0.5812(3) 0.0616(12) Uani 1 1 d . . . . .
C28 C 0.8099(5) -0.5818(4) -0.6194(3) 0.0730(14) Uani 1 1 d . . . . .
H28A H 0.743381 -0.571018 -0.651702 0.088 Uiso 1 1 calc R U . . .
H28B H 0.878197 -0.599197 -0.654405 0.088 Uiso 1 1 calc R U . . .
C29 C 0.8386(4) -0.4718(4) -0.5418(3) 0.0660(13) Uani 1 1 d . . . . .
C30 C 0.8279(4) -0.5048(4) -0.4691(3) 0.0596(11) Uani 1 1 d . . . . .
C31 C 0.8733(5) -0.3507(5) -0.5342(4) 0.0815(17) Uani 1 1 d . . . . .
H31 H 0.881020 -0.327248 -0.581403 0.098 Uiso 1 1 calc R U . . .
C32 C 0.8962(5) -0.2651(5) -0.4559(4) 0.0879(18) Uani 1 1 d . . . . .
H32 H 0.920104 -0.183921 -0.451072 0.105 Uiso 1 1 calc R U . . .
C33 C 0.8846(5) -0.2968(5) -0.3847(4) 0.0892(17) Uani 1 1 d . . . . .
H33 H 0.899697 -0.237443 -0.332498 0.107 Uiso 1 1 calc R U . . .
C34 C 0.8502(5) -0.4185(4) -0.3917(4) 0.0738(14) Uani 1 1 d . . . . .
H34 H 0.842377 -0.441041 -0.344131 0.089 Uiso 1 1 calc R U . . .
C35 C 0.7345(4) -0.8260(4) -0.5101(3) 0.0583(11) Uani 1 1 d . . . . .
C36 C 0.6952(4) -0.9366(4) -0.4054(3) 0.0540(10) Uani 1 1 d . . . . .
H36 H 0.649351 -0.871964 -0.370693 0.065 Uiso 1 1 calc R U . . .
C37 C 0.6235(4) -1.0623(4) -0.4234(3) 0.0584(11) Uani 1 1 d . . . . .
H37A H 0.660165 -1.112115 -0.395987 0.070 Uiso 1 1 calc R U . . .
H37B H 0.542251 -1.053572 -0.405905 0.070 Uiso 1 1 calc R U . . .
C38 C 0.6285(4) -1.1162(4) -0.5166(3) 0.0532(10) Uani 1 1 d . . . . .
C39 C 0.8161(4) -0.9272(3) -0.3643(3) 0.0472(9) Uani 1 1 d . . . . .
C40 C 0.8226(4) -0.9273(4) -0.2831(3) 0.0561(11) Uani 1 1 d . . . . .
H40 H 0.752743 -0.932860 -0.255177 0.067 Uiso 1 1 calc R U . . .
C41 C 0.9309(4) -0.9194(4) -0.2426(3) 0.0599(11) Uani 1 1 d . . . . .
H41 H 0.934775 -0.919487 -0.187980 0.072 Uiso 1 1 calc R U . . .
C42 C 1.0308(4) -0.9116(4) -0.2846(3) 0.0608(11) Uani 1 1 d . . . . .
C43 C 1.0302(4) -0.9117(4) -0.3645(3) 0.0626(12) Uani 1 1 d . . . . .
H43 H 1.101001 -0.906769 -0.391531 0.075 Uiso 1 1 calc R U . . .
C44 C 0.9214(4) -0.9192(4) -0.4045(3) 0.0535(10) Uani 1 1 d . . . . .
H44 H 0.918958 -0.918875 -0.459169 0.064 Uiso 1 1 calc R U . . .
C45 C 0.5863(4) -1.2433(4) -0.5670(3) 0.0522(10) Uani 1 1 d . . . . .
C46 C 0.5211(4) -1.3196(4) -0.5316(3) 0.0631(12) Uani 1 1 d . . . . .
H46 H 0.506257 -1.291512 -0.475032 0.076 Uiso 1 1 calc R U . . .
C47 C 0.4778(5) -1.4382(4) -0.5803(3) 0.0705(13) Uani 1 1 d . . . . .
H47 H 0.431153 -1.488225 -0.557087 0.085 Uiso 1 1 calc R U . . .
C48 C 0.5042(4) -1.4803(4) -0.6624(3) 0.0598(11) Uani 1 1 d . . . . .
C49 C 0.5717(5) -1.4096(4) -0.6979(3) 0.0724(14) Uani 1 1 d . . . . .
H49 H 0.590483 -1.440813 -0.753709 0.087 Uiso 1 1 calc R U . . .
C50 C 0.6126(5) -1.2908(4) -0.6507(3) 0.0677(13) Uani 1 1 d . . . . .
H50 H 0.658327 -1.241867 -0.675138 0.081 Uiso 1 1 calc R U . . .
N1 N 0.7501(3) -0.8388(3) -0.0660(2) 0.0454(8) Uani 1 1 d . . . . .
N2 N 0.7015(3) -0.6367(3) -0.0326(2) 0.0472(8) Uani 1 1 d . . . . .
N3 N 0.6834(3) -0.5267(3) 0.0282(2) 0.0428(7) Uani 1 1 d . . . . .
N4 N 0.7652(3) -0.7184(3) -0.4544(2) 0.0593(9) Uani 1 1 d . . . . .
N5 N 0.7018(4) -0.9287(3) -0.4898(2) 0.0659(11) Uani 1 1 d . . . . .
N6 N 0.6692(3) -1.0389(3) -0.5523(2) 0.0569(9) Uani 1 1 d . . . . .
Br1 Br 0.51139(5) 0.06048(4) 0.18048(4) 0.0835(2) Uani 1 1 d . . . . .
Br2 Br 0.44554(6) -1.64283(5) -0.72785(4) 0.0974(2) Uani 1 1 d . . . . .
S1 S 0.76099(10) -0.71559(9) 0.09420(7) 0.0530(3) Uani 1 1 d . . . . .
S2 S 0.73495(12) -0.83545(11) -0.61521(8) 0.0671(3) Uani 1 1 d . . . . .
F1 F 1.1517(2) -0.5866(3) -0.2468(2) 0.0849(9) Uani 1 1 d . . . . .
F2 F 1.1384(3) -0.8993(3) -0.2442(2) 0.0937(10) 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'
Br Br -0.2901 2.4595 '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
C2 C1 N1 117.7(3) . .
C2 C1 C5 109.2(3) . .
N1 C1 C5 133.1(4) . .
C1 C2 C3 112.4(4) . .
C1 C2 S1 110.2(3) . .
C3 C2 S1 137.2(4) . .
C2 C3 C4 100.4(4) . .
C2 C3 H3A 111.7 . .
C4 C3 H3A 111.7 . .
C2 C3 H3B 111.7 . .
C4 C3 H3B 111.7 . .
H3A C3 H3B 109.5 . .
C6 C4 C5 119.4(4) . .
C6 C4 C3 129.5(4) . .
C5 C4 C3 111.1(3) . .
C9 C5 C4 121.1(4) . .
C9 C5 C1 132.0(4) . .
C4 C5 C1 106.8(4) . .
C4 C6 C7 119.3(5) . .
C4 C6 H6 120.3 . .
C7 C6 H6 120.3 . .
C8 C7 C6 120.8(4) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C9 121.3(5) . .
C7 C8 H8 119.3 . .
C9 C8 H8 119.3 . .
C5 C9 C8 118.0(5) . .
C5 C9 H9 121.0 . .
C8 C9 H9 121.0 . .
N1 C10 N2 122.1(4) . .
N1 C10 S1 117.4(3) . .
N2 C10 S1 120.5(3) . .
N2 C11 C14 113.2(3) . .
N2 C11 C12 100.5(3) . .
C14 C11 C12 112.6(3) . .
N2 C11 H11 110.0 . .
C14 C11 H11 110.0 . .
C12 C11 H11 110.0 . .
C13 C12 C11 102.0(3) . .
C13 C12 H12A 111.4 . .
C11 C12 H12A 111.4 . .
C13 C12 H12B 111.4 . .
C11 C12 H12B 111.4 . .
H12A C12 H12B 109.2 . .
N3 C13 C20 121.7(4) . .
N3 C13 C12 113.5(3) . .
C20 C13 C12 124.8(3) . .
C19 C14 C15 118.6(4) . .
C19 C14 C11 119.0(3) . .
C15 C14 C11 122.3(3) . .
C16 C15 C14 120.9(4) . .
C16 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
C17 C16 C15 118.5(4) . .
C17 C16 H16 120.7 . .
C15 C16 H16 120.7 . .
C16 C17 F1 119.2(4) . .
C16 C17 C18 122.7(4) . .
F1 C17 C18 118.2(4) . .
C17 C18 C19 117.8(4) . .
C17 C18 H18 121.1 . .
C19 C18 H18 121.1 . .
C14 C19 C18 121.4(4) . .
C14 C19 H19 119.3 . .
C18 C19 H19 119.3 . .
C25 C20 C21 118.3(3) . .
C25 C20 C13 121.9(3) . .
C21 C20 C13 119.8(4) . .
C22 C21 C20 120.9(4) . .
C22 C21 H21 119.6 . .
C20 C21 H21 119.6 . .
C23 C22 C21 119.1(4) . .
C23 C22 H22 120.4 . .
C21 C22 H22 120.4 . .
C22 C23 C24 121.9(4) . .
C22 C23 Br1 119.6(3) . .
C24 C23 Br1 118.4(3) . .
C25 C24 C23 118.6(4) . .
C25 C24 H24 120.7 . .
C23 C24 H24 120.7 . .
C24 C25 C20 121.1(4) . .
C24 C25 H25 119.4 . .
C20 C25 H25 119.4 . .
C27 C26 N4 118.3(4) . .
C27 C26 C30 110.1(4) . .
N4 C26 C30 131.6(4) . .
C26 C27 C28 112.3(4) . .
C26 C27 S2 110.3(3) . .
C28 C27 S2 137.4(4) . .
C27 C28 C29 100.4(4) . .
C27 C28 H28A 111.7 . .
C29 C28 H28A 111.7 . .
C27 C28 H28B 111.7 . .
C29 C28 H28B 111.7 . .
H28A C28 H28B 109.5 . .
C31 C29 C30 119.1(5) . .
C31 C29 C28 129.6(5) . .
C30 C29 C28 111.3(4) . .
C34 C30 C29 120.8(4) . .
C34 C30 C26 133.4(5) . .
C29 C30 C26 105.8(4) . .
C32 C31 C29 119.4(5) . .
C32 C31 H31 120.3 . .
C29 C31 H31 120.3 . .
C31 C32 C33 121.6(5) . .
C31 C32 H32 119.2 . .
C33 C32 H32 119.2 . .
C32 C33 C34 119.4(6) . .
C32 C33 H33 120.3 . .
C34 C33 H33 120.3 . .
C30 C34 C33 119.6(5) . .
C30 C34 H34 120.2 . .
C33 C34 H34 120.2 . .
N4 C35 N5 123.0(4) . .
N4 C35 S2 117.4(3) . .
N5 C35 S2 119.6(3) . .
N5 C36 C39 113.0(4) . .
N5 C36 C37 100.7(3) . .
C39 C36 C37 113.8(3) . .
N5 C36 H36 109.6 . .
C39 C36 H36 109.6 . .
C37 C36 H36 109.6 . .
C38 C37 C36 102.1(3) . .
C38 C37 H37A 111.3 . .
C36 C37 H37A 111.3 . .
C38 C37 H37B 111.3 . .
C36 C37 H37B 111.3 . .
H37A C37 H37B 109.2 . .
N6 C38 C45 120.3(4) . .
N6 C38 C37 114.2(4) . .
C45 C38 C37 125.5(4) . .
C40 C39 C44 118.3(4) . .
C40 C39 C36 118.9(4) . .
C44 C39 C36 122.8(4) . .
C41 C40 C39 121.3(4) . .
C41 C40 H40 119.4 . .
C39 C40 H40 119.4 . .
C42 C41 C40 118.2(4) . .
C42 C41 H41 120.9 . .
C40 C41 H41 120.9 . .
C41 C42 C43 123.4(4) . .
C41 C42 F2 118.7(5) . .
C43 C42 F2 118.0(5) . .
C42 C43 C44 118.2(4) . .
C42 C43 H43 120.9 . .
C44 C43 H43 120.9 . .
C43 C44 C39 120.8(4) . .
C43 C44 H44 119.6 . .
C39 C44 H44 119.6 . .
C46 C45 C50 118.2(4) . .
C46 C45 C38 120.7(4) . .
C50 C45 C38 121.2(4) . .
C45 C46 C47 120.3(5) . .
C45 C46 H46 119.8 . .
C47 C46 H46 119.8 . .
C48 C47 C46 119.4(4) . .
C48 C47 H47 120.3 . .
C46 C47 H47 120.3 . .
C49 C48 C47 121.6(4) . .
C49 C48 Br2 119.5(4) . .
C47 C48 Br2 118.9(3) . .
C48 C49 C50 119.4(5) . .
C48 C49 H49 120.3 . .
C50 C49 H49 120.3 . .
C49 C50 C45 121.0(4) . .
C49 C50 H50 119.5 . .
C45 C50 H50 119.5 . .
C10 N1 C1 107.5(3) . .
C10 N2 N3 120.2(3) . .
C10 N2 C11 126.0(3) . .
N3 N2 C11 113.1(3) . .
C13 N3 N2 107.2(3) . .
C35 N4 C26 106.7(4) . .
C35 N5 N6 119.5(4) . .
C35 N5 C36 126.6(4) . .
N6 N5 C36 113.9(3) . .
C38 N6 N5 107.0(4) . .
C2 S1 C10 87.27(19) . .
C27 S2 C35 87.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.352(6) .
C1 N1 1.379(5) .
C1 C5 1.463(5) .
C2 C3 1.500(5) .
C2 S1 1.730(4) .
C3 C4 1.514(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C6 1.380(6) .
C4 C5 1.403(6) .
C5 C9 1.377(6) .
C6 C7 1.393(7) .
C6 H6 0.9300 .
C7 C8 1.352(7) .
C7 H7 0.9300 .
C8 C9 1.401(6) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 N1 1.309(5) .
C10 N2 1.363(5) .
C10 S1 1.748(4) .
C11 N2 1.461(5) .
C11 C14 1.511(5) .
C11 C12 1.537(5) .
C11 H11 0.9800 .
C12 C13 1.498(6) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 N3 1.299(5) .
C13 C20 1.457(5) .
C14 C19 1.377(5) .
C14 C15 1.388(5) .
C15 C16 1.382(6) .
C15 H15 0.9300 .
C16 C17 1.357(6) .
C16 H16 0.9300 .
C17 F1 1.359(5) .
C17 C18 1.379(7) .
C18 C19 1.381(6) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C25 1.392(6) .
C20 C21 1.393(5) .
C21 C22 1.384(5) .
C21 H21 0.9300 .
C22 C23 1.362(6) .
C22 H22 0.9300 .
C23 C24 1.381(6) .
C23 Br1 1.902(4) .
C24 C25 1.380(5) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C26 C27 1.342(7) .
C26 N4 1.388(5) .
C26 C30 1.464(6) .
C27 C28 1.501(6) .
C27 S2 1.724(5) .
C28 C29 1.511(7) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C29 C31 1.384(6) .
C29 C30 1.413(7) .
C30 C34 1.370(7) .
C31 C32 1.379(8) .
C31 H31 0.9300 .
C32 C33 1.379(8) .
C32 H32 0.9300 .
C33 C34 1.394(7) .
C33 H33 0.9300 .
C34 H34 0.9300 .
C35 N4 1.309(5) .
C35 N5 1.365(5) .
C35 S2 1.753(5) .
C36 N5 1.468(6) .
C36 C39 1.510(6) .
C36 C37 1.535(6) .
C36 H36 0.9800 .
C37 C38 1.503(6) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C38 N6 1.291(5) .
C38 C45 1.471(6) .
C39 C40 1.382(6) .
C39 C44 1.385(6) .
C40 C41 1.381(6) .
C40 H40 0.9300 .
C41 C42 1.349(7) .
C41 H41 0.9300 .
C42 C43 1.358(7) .
C42 F2 1.366(5) .
C43 C44 1.385(6) .
C43 H43 0.9300 .
C44 H44 0.9300 .
C45 C46 1.385(6) .
C45 C50 1.389(6) .
C46 C47 1.391(6) .
C46 H46 0.9300 .
C47 C48 1.361(7) .
C47 H47 0.9300 .
C48 C49 1.353(6) .
C48 Br2 1.899(4) .
C49 C50 1.380(6) .
C49 H49 0.9300 .
C50 H50 0.9300 .
N2 N3 1.384(4) .
N5 N6 1.382(5) .
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
C16 H16 N3 0.93 2.68 3.554(5) 156.3 2_745 yes
