##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1870513'
_audit_creation_method     'SHELXL-2018/1'
_journal_date_recd_electronic     2018-09-26
_journal_date_accepted     2018-09-28
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue     10
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618013780
_journal_coeditor_code     SJ4192
_publ_contact_author_name     'Gamal A. El-Hiti'
_publ_contact_author_address
;
Department of Optometry, College of Applied Medical Sciences, King Saud
University, P.O. Box 10219, Riyadh 11433, Saudi Arabia
;
_publ_contact_author_email     'gelhiti@ksu.edu.sa'
_publ_contact_author_fax     '00966(0)114693536'
_publ_contact_author_phone     '00966(0)114693778'
_publ_section_title
;\
5-[(4-Bromophenyl)diazenyl]-2-{2-[1-(1H-indol-3-yl)ethylidene]\
hydrazinyl}-4-methylthiazole dimethylformamide hemisolvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Hiti, Gamal A.' .
;
Department of Optometry, College of Applied Medical Sciences,
King Saud University, PO Box 10219, Riyadh 11433,
Saudi Arabia
;
    'Abdel-Wahab, Bakr F.' .
;
Department of Chemistry, College of Science and Humanities, Shaqra University,
Duwadimi, Saudi Arabia
Applied Organic Chemistry Department,
National Research Centre, Dokki, Giza, Egypt
;
    'Alotaibi, Mohammad Hayal' .
;
National Center for Petrochemicals Technology,
King Abdulaziz City for Science and Technology,
PO Box 6086, Riyadh 11442,
Saudi Arabia
;
    'Yousif, Emad' .
;
Department of Chemistry, College of Science, Al-Nahrain University,
Baghdad 64021, Iraq
;
    'Hegazy, Amany S.' .
;
School of Chemistry, Cardiff University, Main Building, Park Place,
Cardiff CF10 3AT, UK
;
    'Kariuki, Benson M.'
;
Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.
;
;
School of Chemistry, Cardiff University, Main Building, Park Place,
Cardiff CF10 3AT, UK
;
_publ_section_synopsis
;
The asymmetric unit of the title compound comprises two molecules of the
thiazole C₂₀H₁₇BrN₆S, and one molecule of dimethylformamide (DMF)
solvent. N---H...N hydrogen bonding links four main molecules, forming rings
within the crystal. Additional N---H...O hydrogen bonds involving the DMF
solvent also occur.
;
_chemical_name_systematic
;\
5-[(4-Bromophenyl)diazenyl]-2-{2-[1-(1H-indol-3-yl)ethylidene]\
hydrazinyl}-4-methylthiazole dimethylformamide hemisolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C20 H17 Br N6 S), C3 H7 N O'
_chemical_formula_sum     'C43 H41 Br2 N13 O S2'
_chemical_formula_iupac     '2C20 H17 Br N6 S, C3 H7 N O'
_chemical_formula_weight     979.83
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.9957(6)
_cell_length_b     14.5325(9)
_cell_length_c     15.8353(10)
_cell_angle_alpha     81.671(5)
_cell_angle_beta     81.344(5)
_cell_angle_gamma     80.469(5)
_cell_volume     2225.7(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3549
_cell_measurement_theta_min     3.2690
_cell_measurement_theta_max     24.0000
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.247
_exptl_crystal_size_mid     0.090
_exptl_crystal_size_min     0.037
_exptl_crystal_density_diffrn     1.462
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1000
_exptl_absorpt_coefficient_mu     1.965
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_absorpt_correction_T_min     0.827
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
                  'Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19885
_diffrn_reflns_av_R_equivalents     0.0355
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_theta_min     1.311
_diffrn_reflns_theta_max     29.894
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.825
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     10602
_reflns_number_gt     5116
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1383
_refine_ls_R_factor_gt     0.0558
_refine_ls_wR_factor_gt     0.1121
_refine_ls_wR_factor_ref     0.1447
_refine_ls_goodness_of_fit_ref     1.009
_refine_ls_restrained_S_all     1.009
_refine_ls_number_reflns     10602
_refine_ls_number_parameters     556
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0515P)²+0.5647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.492
_refine_diff_density_min     -0.567
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows and WinGX (Farrugia, 2012)
;
_computing_publication_material
;
ORTEP-3 for Windows and WinGX (Farrugia, 2012) and CHEMDRAW Ultra
(Cambridge Soft, 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.3683(4) 0.4890(3) 0.2966(3) 0.0661(11) Uani d 1 . .
    C C2 0.3605(4) 0.5387(3) 0.2167(3) 0.0725(12) Uani d 1 . .
    H H2 0.439015 0.542822 0.177384 0.087 Uiso calc 1 . .
    C C3 0.2340(4) 0.5828(3) 0.1951(3) 0.0690(12) Uani d 1 . .
    H H3 0.227696 0.616794 0.141065 0.083 Uiso calc 1 . .
    C C4 0.1170(3) 0.5764(3) 0.2536(2) 0.0553(10) Uani d 1 . .
    C C5 0.1270(4) 0.5278(3) 0.3346(2) 0.0686(12) Uani d 1 . .
    H H5 0.049302 0.524021 0.374718 0.082 Uiso calc 1 . .
    C C6 0.2539(4) 0.4849(3) 0.3554(3) 0.0755(13) Uani d 1 . .
    H H6 0.261508 0.452795 0.410069 0.091 Uiso calc 1 . .
    C C7 -0.2388(3) 0.6543(3) 0.2642(2) 0.0503(9) Uani d 1 . .
    C C8 -0.3603(3) 0.6609(3) 0.3284(2) 0.0500(9) Uani d 1 . .
    C C9 -0.3516(4) 0.6225(3) 0.4198(2) 0.0662(11) Uani d 1 . .
    H H9A -0.296376 0.657467 0.443928 0.099 Uiso calc 1 . .
    H H9B -0.310921 0.557619 0.423143 0.099 Uiso calc 1 . .
    H H9C -0.441742 0.627509 0.451411 0.099 Uiso calc 1 . .
    C C10 -0.4547(3) 0.7334(3) 0.2135(2) 0.0503(9) Uani d 1 . .
    C C11 -0.7037(4) 0.9302(3) 0.0909(3) 0.0775(13) Uani d 1 . .
    H H11A -0.787420 0.911240 0.081728 0.116 Uiso calc 1 . .
    H H11B -0.702207 0.994822 0.067657 0.116 Uiso calc 1 . .
    H H11C -0.697737 0.922945 0.151532 0.116 Uiso calc 1 . .
    C C12 -0.5837(3) 0.8696(3) 0.0466(2) 0.0532(9) Uani d 1 . .
    C C13 -0.5446(3) 0.8901(3) -0.0446(2) 0.0527(9) Uani d 1 . .
    C C14 -0.5892(4) 0.9712(3) -0.0958(2) 0.0653(11) Uani d 1 . .
    H H14 -0.649707 1.021779 -0.076243 0.078 Uiso calc 1 . .
    C C15 -0.4560(3) 0.8309(3) -0.1020(2) 0.0529(9) Uani d 1 . .
    C C16 -0.4509(4) 0.8814(3) -0.1848(2) 0.0582(10) Uani d 1 . .
    C C17 -0.3895(4) 0.7384(3) -0.0925(3) 0.0678(11) Uani d 1 . .
    H H17 -0.389359 0.703829 -0.038236 0.081 Uiso calc 1 . .
    C C18 -0.3240(4) 0.6987(3) -0.1647(3) 0.0839(14) Uani d 1 . .
    H H18 -0.281517 0.636563 -0.159192 0.101 Uiso calc 1 . .
    C C19 -0.3210(4) 0.7514(4) -0.2458(3) 0.0817(14) Uani d 1 . .
    H H19 -0.275533 0.723225 -0.293336 0.098 Uiso calc 1 . .
    C C20 -0.3824(4) 0.8428(4) -0.2583(3) 0.0717(12) Uani d 1 . .
    H H20 -0.378876 0.877400 -0.312612 0.086 Uiso calc 1 . .
    C C21 0.0369(4) 0.8433(3) 0.8874(2) 0.0685(12) Uani d 1 . .
    C C22 0.1724(4) 0.8075(3) 0.8889(3) 0.0677(11) Uani d 1 . .
    H H22 0.205456 0.785496 0.941102 0.081 Uiso calc 1 . .
    C C23 0.2595(4) 0.8043(3) 0.8127(2) 0.0627(11) Uani d 1 . .
    H H23 0.351116 0.778949 0.813263 0.075 Uiso calc 1 . .
    C C24 0.2104(4) 0.8386(3) 0.7357(2) 0.0562(10) Uani d 1 . .
    C C25 0.0725(4) 0.8708(3) 0.7344(3) 0.0693(12) Uani d 1 . .
    H H25 0.038463 0.891244 0.682330 0.083 Uiso calc 1 . .
    C C26 -0.0152(4) 0.8725(3) 0.8116(3) 0.0752(13) Uani d 1 . .
    H H26 -0.108272 0.893379 0.811442 0.090 Uiso calc 1 . .
    C C27 0.3534(3) 0.8933(3) 0.5193(2) 0.0514(9) Uani d 1 . .
    C C28 0.3153(3) 0.9414(3) 0.4369(2) 0.0540(9) Uani d 1 . .
    C C29 0.1725(4) 0.9861(3) 0.4279(3) 0.0703(12) Uani d 1 . .
    H H29A 0.147110 1.035898 0.463550 0.105 Uiso calc 1 . .
    H H29B 0.111992 0.939995 0.445346 0.105 Uiso calc 1 . .
    H H29C 0.166113 1.011312 0.368891 0.105 Uiso calc 1 . .
    C C30 0.5383(3) 0.9026(3) 0.3979(2) 0.0514(9) Uani d 1 . .
    C C31 0.8812(4) 0.8946(3) 0.2322(2) 0.0685(12) Uani d 1 . .
    H H31A 0.843492 0.855589 0.200746 0.103 Uiso calc 1 . .
    H H31B 0.974539 0.898512 0.208218 0.103 Uiso calc 1 . .
    H H31C 0.829083 0.956467 0.228339 0.103 Uiso calc 1 . .
    C C32 0.8760(4) 0.8529(3) 0.3249(2) 0.0523(9) Uani d 1 . .
    C C33 1.0005(3) 0.8060(3) 0.3569(2) 0.0526(9) Uani d 1 . .
    C C34 1.1291(4) 0.7972(3) 0.3090(2) 0.0624(11) Uani d 1 . .
    H H34 1.147138 0.821149 0.251346 0.075 Uiso calc 1 . .
    C C35 1.0228(3) 0.7596(3) 0.4419(2) 0.0507(9) Uani d 1 . .
    C C36 1.1629(3) 0.7248(3) 0.4387(2) 0.0571(10) Uani d 1 . .
    C C37 0.9387(4) 0.7430(3) 0.5204(2) 0.0646(11) Uani d 1 . .
    H H37 0.845420 0.765264 0.525577 0.077 Uiso calc 1 . .
    C C38 0.9978(4) 0.6929(3) 0.5895(3) 0.0821(15) Uani d 1 . .
    H H38 0.943053 0.681269 0.641737 0.099 Uiso calc 1 . .
    C C39 1.1368(4) 0.6592(4) 0.5834(3) 0.0864(15) Uani d 1 . .
    H H39 1.172934 0.625797 0.631515 0.104 Uiso calc 1 . .
    C C40 1.2216(4) 0.6739(3) 0.5084(3) 0.0726(12) Uani d 1 . .
    H H40 1.314643 0.650980 0.504184 0.087 Uiso calc 1 . .
    C C41 0.0191(5) 0.6113(3) -0.0223(3) 0.0853(14) Uani d 1 . .
    H H41 -0.068023 0.636238 -0.035812 0.102 Uiso calc 1 . .
    C C42 0.0817(7) 0.5992(4) -0.1745(3) 0.119(2) Uani d 1 . .
    H H42A -0.012251 0.626721 -0.175802 0.178 Uiso calc 1 . .
    H H42B 0.096583 0.539015 -0.195353 0.178 Uiso calc 1 . .
    H H42C 0.139772 0.639613 -0.210323 0.178 Uiso calc 1 . .
    C C43 0.2499(6) 0.5465(4) -0.0693(4) 0.127(2) Uani d 1 . .
    H H43A 0.311572 0.591228 -0.090221 0.191 Uiso calc 1 . .
    H H43B 0.278569 0.491202 -0.097807 0.191 Uiso calc 1 . .
    H H43C 0.250381 0.529812 -0.008373 0.191 Uiso calc 1 . .
    N N1 -0.0093(3) 0.6186(2) 0.22832(19) 0.0587(8) Uani d 1 . .
    H H1 -0.015244 0.643112 0.175984 0.070 Uiso calc 1 . .
    N N2 -0.1210(3) 0.6202(2) 0.28697(18) 0.0538(8) Uani d 1 . .
    N N3 -0.4736(3) 0.7028(2) 0.30121(17) 0.0531(8) Uani d 1 . .
    N N4 -0.5533(3) 0.7801(2) 0.17471(18) 0.0578(8) Uani d 1 . .
    N N5 -0.5105(3) 0.7997(2) 0.08630(18) 0.0556(8) Uani d 1 . .
    N N6 -0.5323(3) 0.9668(2) -0.1789(2) 0.0667(9) Uani d 1 . .
    H H6A -0.545184 1.010379 -0.220975 0.080 Uiso calc 1 . .
    N N7 0.3037(3) 0.8407(2) 0.66017(18) 0.0615(9) Uani d 1 . .
    H H7 0.386501 0.813022 0.661312 0.074 Uiso calc 1 . .
    N N8 0.2636(3) 0.8859(2) 0.58613(19) 0.0547(8) Uani d 1 . .
    N N9 0.4131(3) 0.9447(2) 0.37360(18) 0.0552(8) Uani d 1 . .
    N N10 0.6473(3) 0.9013(2) 0.34273(18) 0.0553(8) Uani d 1 . .
    N N11 0.7640(3) 0.8559(2) 0.37912(17) 0.0543(8) Uani d 1 . .
    N N12 1.2240(3) 0.7495(2) 0.3570(2) 0.0676(9) Uani d 1 . .
    H H12 1.309808 0.736557 0.339169 0.081 Uiso calc 1 . .
    N N13 0.1136(4) 0.5873(3) -0.0864(2) 0.0866(12) Uani d 1 . .
    O O1 0.0371(4) 0.6034(3) 0.0529(2) 0.1044(12) Uani d 1 . .
    S S1 -0.28472(9) 0.70423(7) 0.16186(5) 0.0551(3) Uani d 1 . .
    S S2 0.53169(9) 0.85338(7) 0.50777(6) 0.0563(3) Uani d 1 . .
    Br Br1 0.53923(5) 0.42261(4) 0.32500(4) 0.0973(2) Uani d 1 . .
    Br Br2 -0.07975(6) 0.84842(4) 0.99418(3) 0.1142(3) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.365(6) ?
    C1 C2 . 1.369(6) ?
    C1 Br1 . 1.901(3) ?
    C2 C3 . 1.387(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(5) ?
    C4 N1 . 1.398(4) ?
    C5 C6 . 1.382(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N2 . 1.283(4) ?
    C7 C8 . 1.461(4) ?
    C7 S1 . 1.771(3) ?
    C8 N3 . 1.297(4) ?
    C8 C9 . 1.484(5) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 N4 . 1.284(4) ?
    C10 N3 . 1.390(4) ?
    C10 S1 . 1.783(3) ?
    C11 C12 . 1.510(5) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 N5 . 1.292(4) ?
    C12 C13 . 1.441(5) ?
    C13 C14 . 1.379(5) ?
    C13 C15 . 1.442(5) ?
    C14 N6 . 1.358(5) ?
    C14 H14 . 0.9300 ?
    C15 C17 . 1.396(5) ?
    C15 C16 . 1.405(5) ?
    C16 N6 . 1.373(5) ?
    C16 C20 . 1.400(5) ?
    C17 C18 . 1.382(6) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.397(6) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.367(6) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
    C21 C26 . 1.363(6) ?
    C21 C22 . 1.370(6) ?
    C21 Br2 . 1.908(4) ?
    C22 C23 . 1.380(5) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.378(5) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.382(5) ?
    C24 N7 . 1.401(4) ?
    C25 C26 . 1.394(5) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C27 N8 . 1.284(4) ?
    C27 C28 . 1.461(5) ?
    C27 S2 . 1.771(3) ?
    C28 N9 . 1.292(4) ?
    C28 C29 . 1.485(5) ?
    C29 H29A . 0.9600 ?
    C29 H29B . 0.9600 ?
    C29 H29C . 0.9600 ?
    C30 N10 . 1.290(4) ?
    C30 N9 . 1.382(4) ?
    C30 S2 . 1.778(3) ?
    C31 C32 . 1.501(5) ?
    C31 H31A . 0.9600 ?
    C31 H31B . 0.9600 ?
    C31 H31C . 0.9600 ?
    C32 N11 . 1.303(4) ?
    C32 C33 . 1.443(5) ?
    C33 C34 . 1.387(5) ?
    C33 C35 . 1.447(5) ?
    C34 N12 . 1.344(5) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.404(5) ?
    C35 C37 . 1.406(5) ?
    C36 N12 . 1.370(5) ?
    C36 C40 . 1.388(5) ?
    C37 C38 . 1.378(5) ?
    C37 H37 . 0.9300 ?
    C38 C39 . 1.389(5) ?
    C38 H38 . 0.9300 ?
    C39 C40 . 1.363(6) ?
    C39 H39 . 0.9300 ?
    C40 H40 . 0.9300 ?
    C41 O1 . 1.217(5) ?
    C41 N13 . 1.321(6) ?
    C41 H41 . 0.9300 ?
    C42 N13 . 1.458(6) ?
    C42 H42A . 0.9600 ?
    C42 H42B . 0.9600 ?
    C42 H42C . 0.9600 ?
    C43 N13 . 1.442(6) ?
    C43 H43A . 0.9600 ?
    C43 H43B . 0.9600 ?
    C43 H43C . 0.9600 ?
    N1 N2 . 1.340(4) ?
    N1 H1 . 0.8600 ?
    N4 N5 . 1.403(4) ?
    N6 H6A . 0.8600 ?
    N7 N8 . 1.341(4) ?
    N7 H7 . 0.8600 ?
    N10 N11 . 1.401(4) ?
    N12 H12 . 0.8600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 120.7(3) ?
    C6 C1 Br1 . . 119.6(3) ?
    C2 C1 Br1 . . 119.7(3) ?
    C1 C2 C3 . . 119.1(4) ?
    C1 C2 H2 . . 120.4 ?
    C3 C2 H2 . . 120.4 ?
    C4 C3 C2 . . 120.4(4) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 119.7(3) ?
    C5 C4 N1 . . 121.5(3) ?
    C3 C4 N1 . . 118.8(3) ?
    C4 C5 C6 . . 119.1(4) ?
    C4 C5 H5 . . 120.4 ?
    C6 C5 H5 . . 120.4 ?
    C1 C6 C5 . . 120.8(4) ?
    C1 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    N2 C7 C8 . . 120.3(3) ?
    N2 C7 S1 . . 130.1(3) ?
    C8 C7 S1 . . 109.5(2) ?
    N3 C8 C7 . . 116.5(3) ?
    N3 C8 C9 . . 122.6(3) ?
    C7 C8 C9 . . 120.8(3) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N4 C10 N3 . . 121.4(3) ?
    N4 C10 S1 . . 123.9(3) ?
    N3 C10 S1 . . 114.7(2) ?
    C12 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C12 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N5 C12 C13 . . 116.7(3) ?
    N5 C12 C11 . . 123.7(3) ?
    C13 C12 C11 . . 119.6(3) ?
    C14 C13 C12 . . 126.1(3) ?
    C14 C13 C15 . . 105.7(3) ?
    C12 C13 C15 . . 128.2(3) ?
    N6 C14 C13 . . 110.4(3) ?
    N6 C14 H14 . . 124.8 ?
    C13 C14 H14 . . 124.8 ?
    C17 C15 C16 . . 118.6(3) ?
    C17 C15 C13 . . 134.2(3) ?
    C16 C15 C13 . . 106.9(3) ?
    N6 C16 C20 . . 129.0(4) ?
    N6 C16 C15 . . 107.9(3) ?
    C20 C16 C15 . . 122.9(4) ?
    C18 C17 C15 . . 119.2(4) ?
    C18 C17 H17 . . 120.4 ?
    C15 C17 H17 . . 120.4 ?
    C17 C18 C19 . . 120.4(4) ?
    C17 C18 H18 . . 119.8 ?
    C19 C18 H18 . . 119.8 ?
    C20 C19 C18 . . 122.6(4) ?
    C20 C19 H19 . . 118.7 ?
    C18 C19 H19 . . 118.7 ?
    C19 C20 C16 . . 116.3(4) ?
    C19 C20 H20 . . 121.8 ?
    C16 C20 H20 . . 121.8 ?
    C26 C21 C22 . . 121.3(4) ?
    C26 C21 Br2 . . 120.2(3) ?
    C22 C21 Br2 . . 118.4(3) ?
    C21 C22 C23 . . 119.6(4) ?
    C21 C22 H22 . . 120.2 ?
    C23 C22 H22 . . 120.2 ?
    C24 C23 C22 . . 119.9(4) ?
    C24 C23 H23 . . 120.1 ?
    C22 C23 H23 . . 120.1 ?
    C23 C24 C25 . . 120.0(3) ?
    C23 C24 N7 . . 118.3(3) ?
    C25 C24 N7 . . 121.7(3) ?
    C24 C25 C26 . . 119.7(4) ?
    C24 C25 H25 . . 120.2 ?
    C26 C25 H25 . . 120.2 ?
    C21 C26 C25 . . 119.3(4) ?
    C21 C26 H26 . . 120.4 ?
    C25 C26 H26 . . 120.4 ?
    N8 C27 C28 . . 121.0(3) ?
    N8 C27 S2 . . 129.7(3) ?
    C28 C27 S2 . . 109.2(2) ?
    N9 C28 C27 . . 116.2(3) ?
    N9 C28 C29 . . 122.4(3) ?
    C27 C28 C29 . . 121.3(3) ?
    C28 C29 H29A . . 109.5 ?
    C28 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    C28 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    N10 C30 N9 . . 120.3(3) ?
    N10 C30 S2 . . 125.4(3) ?
    N9 C30 S2 . . 114.4(2) ?
    C32 C31 H31A . . 109.5 ?
    C32 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C32 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    N11 C32 C33 . . 117.2(3) ?
    N11 C32 C31 . . 123.7(3) ?
    C33 C32 C31 . . 119.1(3) ?
    C34 C33 C32 . . 125.2(3) ?
    C34 C33 C35 . . 104.9(3) ?
    C32 C33 C35 . . 130.0(3) ?
    N12 C34 C33 . . 110.9(3) ?
    N12 C34 H34 . . 124.6 ?
    C33 C34 H34 . . 124.6 ?
    C36 C35 C37 . . 117.9(3) ?
    C36 C35 C33 . . 107.1(3) ?
    C37 C35 C33 . . 135.0(3) ?
    N12 C36 C40 . . 128.8(3) ?
    N12 C36 C35 . . 107.7(3) ?
    C40 C36 C35 . . 123.4(3) ?
    C38 C37 C35 . . 118.4(3) ?
    C38 C37 H37 . . 120.8 ?
    C35 C37 H37 . . 120.8 ?
    C37 C38 C39 . . 121.8(4) ?
    C37 C38 H38 . . 119.1 ?
    C39 C38 H38 . . 119.1 ?
    C40 C39 C38 . . 121.6(4) ?
    C40 C39 H39 . . 119.2 ?
    C38 C39 H39 . . 119.2 ?
    C39 C40 C36 . . 116.9(3) ?
    C39 C40 H40 . . 121.5 ?
    C36 C40 H40 . . 121.5 ?
    O1 C41 N13 . . 125.2(5) ?
    O1 C41 H41 . . 117.4 ?
    N13 C41 H41 . . 117.4 ?
    N13 C42 H42A . . 109.5 ?
    N13 C42 H42B . . 109.5 ?
    H42A C42 H42B . . 109.5 ?
    N13 C42 H42C . . 109.5 ?
    H42A C42 H42C . . 109.5 ?
    H42B C42 H42C . . 109.5 ?
    N13 C43 H43A . . 109.5 ?
    N13 C43 H43B . . 109.5 ?
    H43A C43 H43B . . 109.5 ?
    N13 C43 H43C . . 109.5 ?
    H43A C43 H43C . . 109.5 ?
    H43B C43 H43C . . 109.5 ?
    N2 N1 C4 . . 118.9(3) ?
    N2 N1 H1 . . 120.5 ?
    C4 N1 H1 . . 120.5 ?
    C7 N2 N1 . . 119.9(3) ?
    C8 N3 C10 . . 111.6(3) ?
    C10 N4 N5 . . 110.8(3) ?
    C12 N5 N4 . . 115.3(3) ?
    C14 N6 C16 . . 109.1(3) ?
    C14 N6 H6A . . 125.5 ?
    C16 N6 H6A . . 125.5 ?
    N8 N7 C24 . . 119.9(3) ?
    N8 N7 H7 . . 120.1 ?
    C24 N7 H7 . . 120.1 ?
    C27 N8 N7 . . 118.7(3) ?
    C28 N9 C30 . . 112.3(3) ?
    C30 N10 N11 . . 112.1(3) ?
    C32 N11 N10 . . 113.7(3) ?
    C34 N12 C36 . . 109.4(3) ?
    C34 N12 H12 . . 125.3 ?
    C36 N12 H12 . . 125.3 ?
    C41 N13 C43 . . 120.0(4) ?
    C41 N13 C42 . . 121.1(5) ?
    C43 N13 C42 . . 118.9(4) ?
    C7 S1 C10 . . 87.65(16) ?
    C27 S2 C30 . . 87.89(16) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 . 0.86 2.08 2.782(4) 138.3 yes
    N6 H6A N9 2_575 0.86 2.62 3.292(4) 135.5 yes
    N6 H6A N10 2_575 0.86 2.42 3.234(4) 158.5 yes
    N12 H12 N3 1_755 0.86 2.15 3.011(4) 177.2 yes
_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     0.642
_shelx_estimated_absorpt_T_max     0.931
