#------------------------------------------------------------------------------
#$Date: 2023-06-23 12:13:38 +0300 (Fri, 23 Jun 2023) $
#$Revision: 284527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107418.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_8107418
loop_
_publ_author_name
'Al-Sanea, Mohammad M.'
'Blacque, Olivier'
'Mohamed, Ahmed A. B.'
'Tiekink, Edward R. T.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide,
 C18H17BrF3N3S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              285
_journal_page_last               288
_journal_paper_doi               10.1515/ncrs-2022-0544
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C18 H17 Br F3 N3 S'
_chemical_formula_sum            'C18 H17 Br F3 N3 S'
_chemical_formula_weight         444.31
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.177(2)
_cell_angle_beta                 97.015(2)
_cell_angle_gamma                91.111(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6380(2)
_cell_length_b                   14.5082(3)
_cell_length_c                   14.8000(3)
_cell_measurement_reflns_used    26402
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.9850
_cell_measurement_theta_min      3.0180
_cell_volume                     1820.89(7)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'OLEX2 [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -126.00 -78.00   0.50    2.59    --  -51.77 -84.00 153.00   96
  2  ω    -77.00  23.00   0.50    2.59    --  -51.77  84.00 -86.00  200
  3  ω    -22.00  78.00   0.50    2.59    --   51.77 -84.00 153.00  200
  4  ω   -161.00 -78.00   0.50    6.20    --  -86.25 -84.00 153.00  166
  5  ω   -112.00 -11.00   0.50    6.20    --  -86.25  84.00 -86.00  202
  6  ω     33.00 134.00   0.50    6.20    --  107.75 -84.00 153.00  202
  7  ω    100.00 178.00   0.50    6.20    --  107.75  84.00 -86.00  156
  8  ω   -124.00 -37.00   0.50    2.59    --  -51.77 -57.00 -30.00  174
  9  ω   -126.00 -73.00   0.50    2.59    --  -51.77-125.00-150.00  106
 10  ω   -126.00 -73.00   0.50    2.59    --  -51.77-125.00 -30.00  106
 11  ω   -126.00 -73.00   0.50    2.59    --  -51.77-125.00  30.00  106
 12  ω   -124.00 -37.00   0.50    2.59    --  -51.77 -57.00-180.00  174
 13  ω     34.00  99.00   0.50    2.59    --   51.77-125.00  30.00  130
 14  ω    -21.00  67.00   0.50    2.59    --   51.77 -57.00  30.00  176
 15  ω   -159.00 -65.00   0.50    6.20    --  -86.25 -73.00  56.57  188
 16  ω     31.00 109.00   0.50    6.20    --  107.75-111.00 150.00  156
 17  ω     96.00 178.00   0.50    6.20    --  107.75  15.00   0.00  164
 18  ω     31.00 106.00   0.50    6.20    --  107.75 -94.00   0.00  150
 19  ω     32.00 120.00   0.50    6.20    --  107.75 -45.00 150.00  176
 20  ω     31.00 109.00   0.50    6.20    --  107.75-111.00-150.00  156
 21  ω     62.00 146.00   0.50    6.20    --  107.75 178.00-180.00  168
 22  ω     94.00 178.00   0.50    6.20    --  107.75  30.00-180.00  168
 23  ω     96.00 178.00   0.50    6.20    --  107.75  15.00  90.00  164
 24  ω    102.00 178.00   0.50    6.20    --  107.75 111.00  30.00  152
 25  ω     30.00 120.00   0.50    6.20    --  107.75 -30.00 150.00  180
 26  ω     31.00 106.00   0.50    6.20    --  107.75 -94.00  60.00  150
 27  ω     31.00 109.00   0.50    6.20    --  107.75-111.00 -30.00  156
 28  ω     31.00 106.00   0.50    6.20    --  107.75 -94.00 150.00  150
 29  ω     31.00 106.00   0.50    6.20    --  107.75 -94.00-120.00  150
 30  ω     31.00 109.00   0.50    6.20    --  107.75-111.00  60.00  156
 31  ω     31.00 109.00   0.50    6.20    --  107.75-111.00 -60.00  156
 32  ω     92.00 178.00   0.50    6.20    --  107.75  61.00 -30.00  172
 33  ω     31.00 106.00   0.50    6.20    --  107.75 -94.00 120.00  150
 34  ω     31.00 105.00   0.50    6.20    --  107.75 -94.00 -30.00  148
 35  ω    126.00 178.00   0.50    6.20    --  107.75  15.00  30.00  104
 36  ω     58.00 109.00   0.50    6.20    --  107.75-111.00  90.00  102
 37  ω     56.00  82.00   0.50    6.20    --  107.75 -45.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0700594000
_diffrn_orient_matrix_UB_12      0.0766145000
_diffrn_orient_matrix_UB_13      0.0780251000
_diffrn_orient_matrix_UB_21      -0.1432540000
_diffrn_orient_matrix_UB_22      -0.0107434000
_diffrn_orient_matrix_UB_23      0.0507794000
_diffrn_orient_matrix_UB_31      0.0830934000
_diffrn_orient_matrix_UB_32      -0.0744250000
_diffrn_orient_matrix_UB_33      0.0507086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38076
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.500
_diffrn_reflns_theta_min         3.041
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.484
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0296
_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)+(0.0344P)²+1.8644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6960
_reflns_number_total             7420
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0544_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8107418
_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_max   0.916
_shelx_estimated_absorpt_t_min   0.439
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
Br1 Br 0.02986(3) 0.32258(2) 0.12114(2) 0.03529(7) Uani 1 1 d . . . . .
S1 S 0.20919(5) 0.13799(3) 0.52076(3) 0.02374(10) Uani 1 1 d . . . . .
F1 F 1.31551(16) 0.22694(12) 0.78143(10) 0.0506(4) Uani 1 1 d . . . . .
F2 F 1.39456(18) 0.19727(13) 0.91713(14) 0.0662(5) Uani 1 1 d . . . . .
F3 F 1.25805(19) 0.31559(10) 0.89827(11) 0.0516(4) Uani 1 1 d . . . . .
N1 N 0.44623(19) 0.19903(12) 0.44082(12) 0.0245(3) Uani 1 1 d . . . . .
H1 H 0.531(3) 0.2284(19) 0.4534(19) 0.036(7) Uiso 1 1 d . . . . .
N2 N 0.51512(18) 0.12134(11) 0.56345(11) 0.0217(3) Uani 1 1 d . . . . .
N3 N 0.76185(18) 0.09660(11) 0.70631(11) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.1632(2) 0.28321(14) 0.21907(13) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.1534(2) 0.19098(15) 0.23319(14) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.083563 0.147744 0.193001 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2469(2) 0.16222(14) 0.30690(14) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.242293 0.098967 0.316686 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3467(2) 0.22645(13) 0.36599(13) 0.0216(4) Uani 1 1 d . . . . .
C5 C 0.3587(2) 0.31805(13) 0.34923(14) 0.0239(4) Uani 1 1 d . . . . .
H5 H 0.430063 0.361156 0.388483 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2667(2) 0.34690(14) 0.27516(14) 0.0251(4) Uani 1 1 d . . . . .
H6 H 0.274896 0.409374 0.263372 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3999(2) 0.15322(12) 0.50757(13) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.4848(2) 0.07597(14) 0.64187(14) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.493807 0.007768 0.626455 0.031 Uiso 1 1 calc R U . . .
H8B H 0.377357 0.088163 0.655959 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6007(2) 0.11258(15) 0.72519(14) 0.0277(4) Uani 1 1 d . . . . .
H9A H 0.587521 0.180182 0.742420 0.033 Uiso 1 1 calc R U . . .
H9B H 0.579634 0.081014 0.777735 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7940(2) 0.14197(14) 0.62798(13) 0.0237(4) Uani 1 1 d . . . . .
H10A H 0.900683 0.127762 0.613530 0.028 Uiso 1 1 calc R U . . .
H10B H 0.789288 0.210336 0.644413 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6771(2) 0.10914(13) 0.54384(13) 0.0227(4) Uani 1 1 d . . . . .
H11A H 0.696480 0.144702 0.493735 0.027 Uiso 1 1 calc R U . . .
H11B H 0.691949 0.042463 0.522447 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8746(2) 0.11135(13) 0.78500(14) 0.0252(4) Uani 1 1 d . . . . .
C13 C 1.0182(2) 0.15724(13) 0.78545(14) 0.0251(4) Uani 1 1 d . . . . .
H13 H 1.042415 0.180323 0.731690 0.030 Uiso 1 1 calc R U . . .
C14 C 1.1261(2) 0.16924(14) 0.86450(15) 0.0277(4) Uani 1 1 d . . . . .
C15 C 1.0961(3) 0.13708(17) 0.94423(16) 0.0373(5) Uani 1 1 d . . . . .
H15 H 1.171003 0.145448 0.997603 0.045 Uiso 1 1 calc R U . . .
C16 C 0.9527(3) 0.0921(2) 0.94383(18) 0.0455(6) Uani 1 1 d . . . . .
H16 H 0.928431 0.070452 0.998241 0.055 Uiso 1 1 calc R U . . .
C17 C 0.8449(3) 0.07832(17) 0.86598(17) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.748800 0.045849 0.867223 0.045 Uiso 1 1 calc R U . . .
C18 C 1.2730(3) 0.22557(16) 0.86574(16) 0.0339(5) Uani 1 1 d . . . . .
Br2 Br -0.44430(3) 0.06290(2) 0.10760(2) 0.04414(8) Uani 1 1 d . . . . .
S2 S -0.28605(5) 0.36486(3) 0.52555(3) 0.02317(10) Uani 1 1 d . . . . .
F4 F 0.81934(17) 0.34564(12) 0.79008(10) 0.0499(4) Uani 1 1 d . . . . .
F5 F 0.90840(19) 0.42944(12) 0.91585(15) 0.0702(6) Uani 1 1 d . . . . .
F6 F 0.7446(2) 0.31742(13) 0.91454(14) 0.0663(5) Uani 1 1 d . . . . .
N4 N -0.05632(19) 0.27716(11) 0.44524(12) 0.0235(3) Uani 1 1 d . . . . .
H4 H 0.030(3) 0.2506(18) 0.4569(18) 0.033(7) Uiso 1 1 d . . . . .
N5 N 0.02240(18) 0.39313(11) 0.56546(11) 0.0217(3) Uani 1 1 d . . . . .
N6 N 0.27815(18) 0.46454(11) 0.70017(11) 0.0221(3) Uani 1 1 d . . . . .
C19 C -0.3261(2) 0.12955(14) 0.21486(14) 0.0269(4) Uani 1 1 d . . . . .
C20 C -0.3463(2) 0.22411(14) 0.23598(14) 0.0270(4) Uani 1 1 d . . . . .
H20 H -0.419724 0.254532 0.198283 0.032 Uiso 1 1 calc R U . . .
C21 C -0.2585(2) 0.27427(14) 0.31277(14) 0.0249(4) Uani 1 1 d . . . . .
H21 H -0.268984 0.339641 0.326756 0.030 Uiso 1 1 calc R U . . .
C22 C -0.1551(2) 0.22833(13) 0.36913(13) 0.0212(4) Uani 1 1 d . . . . .
C23 C -0.1372(2) 0.13288(13) 0.34686(14) 0.0245(4) Uani 1 1 d . . . . .
H23 H -0.066301 0.101693 0.385320 0.029 Uiso 1 1 calc R U . . .
C24 C -0.2220(2) 0.08300(14) 0.26898(15) 0.0283(4) Uani 1 1 d . . . . .
H24 H -0.208802 0.018089 0.253200 0.034 Uiso 1 1 calc R U . . .
C25 C -0.0975(2) 0.34492(12) 0.51099(13) 0.0200(4) Uani 1 1 d . . . . .
C26 C -0.0018(2) 0.46232(13) 0.64427(14) 0.0248(4) Uani 1 1 d . . . . .
H26A H -0.107314 0.452448 0.661682 0.030 Uiso 1 1 calc R U . . .
H26B H 0.005411 0.525714 0.627319 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1203(2) 0.45378(14) 0.72517(13) 0.0246(4) Uani 1 1 d . . . . .
H27A H 0.105376 0.502209 0.777355 0.030 Uiso 1 1 calc R U . . .
H27B H 0.107393 0.392068 0.745092 0.030 Uiso 1 1 calc R U . . .
C28 C 0.3026(2) 0.39209(13) 0.62448(13) 0.0237(4) Uani 1 1 d . . . . .
H28A H 0.292659 0.329932 0.643910 0.028 Uiso 1 1 calc R U . . .
H28B H 0.409020 0.399730 0.607522 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1825(2) 0.39919(14) 0.54223(13) 0.0231(4) Uani 1 1 d . . . . .
H29A H 0.199566 0.459187 0.519707 0.028 Uiso 1 1 calc R U . . .
H29B H 0.196463 0.348320 0.492042 0.028 Uiso 1 1 calc R U . . .
C30 C 0.3984(2) 0.48190(13) 0.77514(13) 0.0217(4) Uani 1 1 d . . . . .
C31 C 0.5299(2) 0.42774(13) 0.78379(13) 0.0234(4) Uani 1 1 d . . . . .
H31 H 0.540025 0.375087 0.739046 0.028 Uiso 1 1 calc R U . . .
C32 C 0.6461(2) 0.45088(14) 0.85792(14) 0.0246(4) Uani 1 1 d . . . . .
C33 C 0.6372(2) 0.52789(14) 0.92368(14) 0.0272(4) Uani 1 1 d . . . . .
H33 H 0.718308 0.543501 0.973317 0.033 Uiso 1 1 calc R U . . .
C34 C 0.5063(2) 0.58188(14) 0.91513(14) 0.0272(4) Uani 1 1 d . . . . .
H34 H 0.497665 0.634978 0.959630 0.033 Uiso 1 1 calc R U . . .
C35 C 0.3884(2) 0.55925(13) 0.84271(13) 0.0246(4) Uani 1 1 d . . . . .
H35 H 0.299416 0.596584 0.838610 0.029 Uiso 1 1 calc R U . . .
C36 C 0.7791(3) 0.38692(15) 0.87015(15) 0.0312(4) 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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0175
0 0 -1 0.0010
0 -1 0 0.0024
0 1 0 0.0224
-1 0 0 0.1020
3 -7 -3 0.0552
5 3 -3 0.1080
0 5 -3 0.0153
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
C7 N1 C4 125.80(16) . .
C7 N1 H1 116.4(19) . .
C4 N1 H1 114.6(19) . .
C7 N2 C8 122.38(16) . .
C7 N2 C11 125.31(16) . .
C8 N2 C11 111.12(15) . .
C12 N3 C10 116.66(16) . .
C12 N3 C9 114.53(16) . .
C10 N3 C9 110.02(15) . .
C6 C1 C2 121.40(18) . .
C6 C1 Br1 119.59(15) . .
C2 C1 Br1 119.01(15) . .
C1 C2 C3 119.40(19) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C4 C3 C2 119.73(18) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 120.12(18) . .
C5 C4 N1 118.56(17) . .
C3 C4 N1 121.18(17) . .
C4 C5 C6 120.31(18) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C1 C6 C5 118.95(18) . .
C1 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
N2 C7 N1 115.85(17) . .
N2 C7 S1 121.83(14) . .
N1 C7 S1 122.31(14) . .
N2 C8 C9 110.11(16) . .
N2 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
N2 C8 H8B 109.6 . .
C9 C8 H8B 109.6 . .
H8A C8 H8B 108.2 . .
N3 C9 C8 111.10(17) . .
N3 C9 H9A 109.4 . .
C8 C9 H9A 109.4 . .
N3 C9 H9B 109.4 . .
C8 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
N3 C10 C11 111.16(16) . .
N3 C10 H10A 109.4 . .
C11 C10 H10A 109.4 . .
N3 C10 H10B 109.4 . .
C11 C10 H10B 109.4 . .
H10A C10 H10B 108.0 . .
N2 C11 C10 111.87(16) . .
N2 C11 H11A 109.2 . .
C10 C11 H11A 109.2 . .
N2 C11 H11B 109.2 . .
C10 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C13 C12 C17 117.68(19) . .
C13 C12 N3 122.29(18) . .
C17 C12 N3 120.02(19) . .
C14 C13 C12 120.1(2) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C15 C14 C13 122.0(2) . .
C15 C14 C18 118.78(19) . .
C13 C14 C18 119.0(2) . .
C14 C15 C16 117.8(2) . .
C14 C15 H15 121.1 . .
C16 C15 H15 121.1 . .
C17 C16 C15 121.3(2) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C16 C17 C12 121.2(2) . .
C16 C17 H17 119.4 . .
C12 C17 H17 119.4 . .
F2 C18 F3 106.21(19) . .
F2 C18 F1 106.9(2) . .
F3 C18 F1 104.2(2) . .
F2 C18 C14 113.7(2) . .
F3 C18 C14 111.96(18) . .
F1 C18 C14 113.17(18) . .
C25 N4 C22 127.12(16) . .
C25 N4 H4 117.8(18) . .
C22 N4 H4 113.1(18) . .
C25 N5 C26 122.11(16) . .
C25 N5 C29 124.68(16) . .
C26 N5 C29 111.81(15) . .
C30 N6 C28 117.29(15) . .
C30 N6 C27 115.28(15) . .
C28 N6 C27 109.95(15) . .
C24 C19 C20 121.70(18) . .
C24 C19 Br2 119.65(15) . .
C20 C19 Br2 118.65(15) . .
C19 C20 C21 119.46(19) . .
C19 C20 H20 120.3 . .
C21 C20 H20 120.3 . .
C20 C21 C22 119.70(18) . .
C20 C21 H21 120.1 . .
C22 C21 H21 120.1 . .
C21 C22 C23 119.85(17) . .
C21 C22 N4 121.82(17) . .
C23 C22 N4 118.11(17) . .
C24 C23 C22 120.55(19) . .
C24 C23 H23 119.7 . .
C22 C23 H23 119.7 . .
C19 C24 C23 118.70(18) . .
C19 C24 H24 120.7 . .
C23 C24 H24 120.7 . .
N5 C25 N4 115.43(16) . .
N5 C25 S2 122.16(14) . .
N4 C25 S2 122.38(14) . .
N5 C26 C27 110.02(15) . .
N5 C26 H26A 109.7 . .
C27 C26 H26A 109.7 . .
N5 C26 H26B 109.7 . .
C27 C26 H26B 109.7 . .
H26A C26 H26B 108.2 . .
N6 C27 C26 110.82(16) . .
N6 C27 H27A 109.5 . .
C26 C27 H27A 109.5 . .
N6 C27 H27B 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 108.1 . .
N6 C28 C29 109.46(15) . .
N6 C28 H28A 109.8 . .
C29 C28 H28A 109.8 . .
N6 C28 H28B 109.8 . .
C29 C28 H28B 109.8 . .
H28A C28 H28B 108.2 . .
N5 C29 C28 111.76(16) . .
N5 C29 H29A 109.3 . .
C28 C29 H29A 109.3 . .
N5 C29 H29B 109.3 . .
C28 C29 H29B 109.3 . .
H29A C29 H29B 107.9 . .
C31 C30 C35 118.10(17) . .
C31 C30 N6 123.24(17) . .
C35 C30 N6 118.62(17) . .
C32 C31 C30 120.02(18) . .
C32 C31 H31 120.0 . .
C30 C31 H31 120.0 . .
C33 C32 C31 121.82(18) . .
C33 C32 C36 119.11(18) . .
C31 C32 C36 118.94(18) . .
C32 C33 C34 118.18(18) . .
C32 C33 H33 120.9 . .
C34 C33 H33 120.9 . .
C35 C34 C33 120.87(18) . .
C35 C34 H34 119.6 . .
C33 C34 H34 119.6 . .
C34 C35 C30 120.98(18) . .
C34 C35 H35 119.5 . .
C30 C35 H35 119.5 . .
F6 C36 F5 106.9(2) . .
F6 C36 F4 105.01(19) . .
F5 C36 F4 105.70(19) . .
F6 C36 C32 112.31(18) . .
F5 C36 C32 113.51(18) . .
F4 C36 C32 112.79(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.8994(19) .
S1 C7 1.6963(19) .
F1 C18 1.346(3) .
F2 C18 1.327(3) .
F3 C18 1.341(3) .
N1 C7 1.361(3) .
N1 C4 1.425(2) .
N1 H1 0.83(3) .
N2 C7 1.347(2) .
N2 C8 1.461(2) .
N2 C11 1.472(2) .
N3 C12 1.412(2) .
N3 C10 1.464(2) .
N3 C9 1.469(3) .
C1 C6 1.382(3) .
C1 C2 1.386(3) .
C2 C3 1.394(3) .
C2 H2 0.9500 .
C3 C4 1.389(3) .
C3 H3 0.9500 .
C4 C5 1.390(3) .
C5 C6 1.393(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C8 C9 1.515(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.518(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.396(3) .
C12 C17 1.402(3) .
C13 C14 1.392(3) .
C13 H13 0.9500 .
C14 C15 1.380(3) .
C14 C18 1.493(3) .
C15 C16 1.387(4) .
C15 H15 0.9500 .
C16 C17 1.379(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
Br2 C19 1.9045(19) .
S2 C25 1.6938(19) .
F4 C36 1.338(3) .
F5 C36 1.325(3) .
F6 C36 1.327(3) .
N4 C25 1.366(2) .
N4 C22 1.419(2) .
N4 H4 0.86(3) .
N5 C25 1.349(2) .
N5 C26 1.465(2) .
N5 C29 1.470(2) .
N6 C30 1.415(2) .
N6 C28 1.461(2) .
N6 C27 1.467(2) .
C19 C24 1.381(3) .
C19 C20 1.382(3) .
C20 C21 1.389(3) .
C20 H20 0.9500 .
C21 C22 1.392(3) .
C21 H21 0.9500 .
C22 C23 1.393(3) .
C23 C24 1.388(3) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C26 C27 1.517(3) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 C29 1.517(3) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.397(3) .
C30 C35 1.404(3) .
C31 C32 1.392(3) .
C31 H31 0.9500 .
C32 C33 1.383(3) .
C32 C36 1.501(3) .
C33 C34 1.392(3) .
C33 H33 0.9500 .
C34 C35 1.383(3) .
C34 H34 0.9500 .
C35 H35 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
C6 C1 C2 C3 1.7(3) . . . .
Br1 C1 C2 C3 -177.72(15) . . . .
C1 C2 C3 C4 1.0(3) . . . .
C2 C3 C4 C5 -3.0(3) . . . .
C2 C3 C4 N1 -178.66(18) . . . .
C7 N1 C4 C5 129.9(2) . . . .
C7 N1 C4 C3 -54.4(3) . . . .
C3 C4 C5 C6 2.4(3) . . . .
N1 C4 C5 C6 178.16(18) . . . .
C2 C1 C6 C5 -2.3(3) . . . .
Br1 C1 C6 C5 177.11(14) . . . .
C4 C5 C6 C1 0.2(3) . . . .
C8 N2 C7 N1 176.07(17) . . . .
C11 N2 C7 N1 -17.5(3) . . . .
C8 N2 C7 S1 -3.3(3) . . . .
C11 N2 C7 S1 163.12(14) . . . .
C4 N1 C7 N2 170.05(18) . . . .
C4 N1 C7 S1 -10.6(3) . . . .
C7 N2 C8 C9 -135.82(18) . . . .
C11 N2 C8 C9 56.1(2) . . . .
C12 N3 C9 C8 -167.89(16) . . . .
C10 N3 C9 C8 58.4(2) . . . .
N2 C8 C9 N3 -58.6(2) . . . .
C12 N3 C10 C11 171.56(16) . . . .
C9 N3 C10 C11 -55.8(2) . . . .
C7 N2 C11 C10 137.82(18) . . . .
C8 N2 C11 C10 -54.5(2) . . . .
N3 C10 C11 N2 54.3(2) . . . .
C10 N3 C12 C13 -7.5(3) . . . .
C9 N3 C12 C13 -138.00(19) . . . .
C10 N3 C12 C17 173.44(19) . . . .
C9 N3 C12 C17 42.9(3) . . . .
C17 C12 C13 C14 -0.2(3) . . . .
N3 C12 C13 C14 -179.36(18) . . . .
C12 C13 C14 C15 -0.1(3) . . . .
C12 C13 C14 C18 -174.82(18) . . . .
C13 C14 C15 C16 -0.4(3) . . . .
C18 C14 C15 C16 174.3(2) . . . .
C14 C15 C16 C17 1.2(4) . . . .
C15 C16 C17 C12 -1.7(4) . . . .
C13 C12 C17 C16 1.1(3) . . . .
N3 C12 C17 C16 -179.7(2) . . . .
C15 C14 C18 F2 37.2(3) . . . .
C13 C14 C18 F2 -148.0(2) . . . .
C15 C14 C18 F3 -83.2(3) . . . .
C13 C14 C18 F3 91.6(2) . . . .
C15 C14 C18 F1 159.4(2) . . . .
C13 C14 C18 F1 -25.8(3) . . . .
C24 C19 C20 C21 1.0(3) . . . .
Br2 C19 C20 C21 -178.54(15) . . . .
C19 C20 C21 C22 -2.1(3) . . . .
C20 C21 C22 C23 1.7(3) . . . .
C20 C21 C22 N4 176.30(18) . . . .
C25 N4 C22 C21 46.8(3) . . . .
C25 N4 C22 C23 -138.6(2) . . . .
C21 C22 C23 C24 -0.2(3) . . . .
N4 C22 C23 C24 -174.97(18) . . . .
C20 C19 C24 C23 0.6(3) . . . .
Br2 C19 C24 C23 -179.94(15) . . . .
C22 C23 C24 C19 -1.0(3) . . . .
C26 N5 C25 N4 -174.49(17) . . . .
C29 N5 C25 N4 20.1(3) . . . .
C26 N5 C25 S2 3.6(3) . . . .
C29 N5 C25 S2 -161.80(15) . . . .
C22 N4 C25 N5 -167.51(18) . . . .
C22 N4 C25 S2 14.4(3) . . . .
C25 N5 C26 C27 138.89(18) . . . .
C29 N5 C26 C27 -54.0(2) . . . .
C30 N6 C27 C26 164.31(16) . . . .
C28 N6 C27 C26 -60.4(2) . . . .
N5 C26 C27 N6 57.1(2) . . . .
C30 N6 C28 C29 -166.58(16) . . . .
C27 N6 C28 C29 59.1(2) . . . .
C25 N5 C29 C28 -138.77(18) . . . .
C26 N5 C29 C28 54.5(2) . . . .
N6 C28 C29 N5 -56.5(2) . . . .
C28 N6 C30 C31 -6.3(3) . . . .
C27 N6 C30 C31 125.6(2) . . . .
C28 N6 C30 C35 171.34(18) . . . .
C27 N6 C30 C35 -56.7(2) . . . .
C35 C30 C31 C32 0.2(3) . . . .
N6 C30 C31 C32 177.85(18) . . . .
C30 C31 C32 C33 -1.2(3) . . . .
C30 C31 C32 C36 174.68(19) . . . .
C31 C32 C33 C34 1.2(3) . . . .
C36 C32 C33 C34 -174.68(19) . . . .
C32 C33 C34 C35 -0.2(3) . . . .
C33 C34 C35 C30 -0.8(3) . . . .
C31 C30 C35 C34 0.8(3) . . . .
N6 C30 C35 C34 -177.00(18) . . . .
C33 C32 C36 F6 91.7(2) . . . .
C31 C32 C36 F6 -84.3(3) . . . .
C33 C32 C36 F5 -29.7(3) . . . .
C31 C32 C36 F5 154.3(2) . . . .
C33 C32 C36 F4 -149.9(2) . . . .
C31 C32 C36 F4 34.1(3) . . . .
