# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_0918_2_0ma-publish
_audit_block_doi                 10.5517/ccdc.csd.cc2fbyh7
_database_code_depnum_ccdc_archive 'CCDC 2244849'
loop_
_audit_author_name
_audit_author_address
'Cao Jindong'
;University Of Science and Technology Beijing
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br6, C9 H12.5 O S, C9 H15 N3'
_chemical_formula_sum            'C18 H27.50 Bi Br6 N3 O S'
_chemical_formula_weight         1022.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Bi Bi -4.1077 10.2566 '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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8987(6)
_cell_length_b                   16.3369(12)
_cell_length_c                   17.8274(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2882.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7842
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.520
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    2.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1894
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40191
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.285
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4294
_reflns_number_total             5067
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.459
_refine_diff_density_min         -1.420
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 
;
 Flack x determined using 1657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+5.6286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0891
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-C14 = C13-C12 = C0AA-C17
 1.36 with sigma of 0.02
 H2A-H3
 2.2 with sigma of 0.02
 H2B-H3
 2.2 with sigma of 0.02
3. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C16, C14, C15, C13, C12, C0AA, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C12, C18A, O1, C17, C16, C0AA, C14, C15, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C14, C16, C17, C12, C0AA, C18A, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, O1, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C17 \\sim C0AA \\sim C12 \\sim C13 \\sim C14 \\sim C16 \\sim C15: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim S1 \\sim C11 \\sim C10: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C14) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C16) \\sim Ueq:
with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C18A) = Uanis(C0AA)
Uanis(C14) = Uanis(C15) = Uanis(C16) = Uanis(C17) = Uanis(C0AA) = Uanis(C12) =
Uanis(C13) = Uanis(C18A) = Uanis(C11) = Uanis(C10)
5. Others
 1*[Sof(C0AA)+Sof(C18A)+Sof(H12)]+1*[Sof(C0AA)+Sof(C18A)+Sof(H12)]=1 with esd
 of 0.01
 Sof(C0AA)=Sof(H12)=1-FVAR(1)
 Sof(C18A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C7(H7), C9(H9), C6(H6), C12(H12), C13(H13), C16(H16), C17(H17)
6.c Fitted hexagon refined as free rotating group:
 C18A(C12,C13,C14,C16,C17)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Bi1 Bi -0.87926(6) -0.39157(3) -0.15280(3) 0.03601(15) Uani 1 1 d . . . . .
Br4 Br -0.87247(16) -0.22579(8) -0.08742(8) 0.0364(3) Uani 1 1 d . . . . .
Br6 Br -1.08976(14) -0.42108(9) -0.03936(9) 0.0411(4) Uani 1 1 d . . . . .
Br2 Br -1.08858(14) -0.33859(11) -0.24751(9) 0.0461(4) Uani 1 1 d . . . . .
Br5 Br -0.65529(15) -0.42599(10) -0.05336(10) 0.0461(4) Uani 1 1 d . . . . .
Br3 Br -0.69535(15) -0.34399(11) -0.26237(10) 0.0462(4) Uani 1 1 d . . . . .
Br1 Br -0.88520(18) -0.55058(9) -0.20734(10) 0.0519(4) Uani 1 1 d . . . . .
S1 S -0.9107(5) -0.8957(3) -0.0673(3) 0.0701(11) Uani 1 1 d . U . . .
N1 N -0.7424(12) -0.2597(7) 0.0850(7) 0.038(3) Uani 1 1 d . . . . .
H1A H -0.756626 -0.274295 0.036364 0.046 Uiso 1 1 calc R U . . .
H1B H -0.670798 -0.224803 0.086281 0.046 Uiso 1 1 calc R U . . .
N3 N -1.1658(11) -0.3627(8) 0.2069(8) 0.047(3) Uani 1 1 d . . . . .
H3 H -1.190108 -0.323349 0.176032 0.056 Uiso 1 1 calc DR U . . .
N2 N -0.9512(11) -0.3478(7) 0.1615(8) 0.039(3) Uani 1 1 d . . . . .
C1 C -0.8670(15) -0.2165(8) 0.1150(9) 0.042(3) Uani 1 1 d . . . . .
H1C H -0.889723 -0.170269 0.081367 0.050 Uiso 1 1 calc R U . . .
H1D H -0.846261 -0.193524 0.165125 0.050 Uiso 1 1 calc R U . . .
C3 C -0.8321(13) -0.3900(9) 0.1298(9) 0.043(4) Uani 1 1 d . . . . .
H3A H -0.852220 -0.407764 0.077899 0.051 Uiso 1 1 calc R U . . .
H3B H -0.811822 -0.439333 0.160010 0.051 Uiso 1 1 calc R U . . .
C4 C -0.7102(13) -0.3337(9) 0.1295(9) 0.037(3) Uani 1 1 d . . . . .
H4A H -0.686931 -0.317864 0.181536 0.045 Uiso 1 1 calc R U . . .
H4B H -0.631632 -0.362257 0.107335 0.045 Uiso 1 1 calc R U . . .
C8 C -1.2318(16) -0.4592(10) 0.2982(9) 0.048(4) Uani 1 1 d . . . . .
H8 H -1.296986 -0.481834 0.331312 0.057 Uiso 1 1 calc R U . . .
C7 C -1.1040(19) -0.4922(10) 0.2929(9) 0.057(5) Uani 1 1 d . . . . .
H7 H -1.083292 -0.540586 0.320133 0.069 Uiso 1 1 calc R U . . .
C2 C -0.9866(13) -0.2716(9) 0.1213(8) 0.038(4) Uani 1 1 d . . . . .
H2A H -1.059882 -0.243037 0.148520 0.046 Uiso 1 1 calc DR U . . .
H2B H -1.020040 -0.285300 0.070486 0.046 Uiso 1 1 calc DR U . . .
C5 C -1.0388(13) -0.3883(10) 0.2041(8) 0.037(3) Uani 1 1 d . . . . .
C9 C -1.2619(15) -0.3933(10) 0.2547(9) 0.046(4) Uani 1 1 d . . . . .
H9 H -1.348759 -0.368690 0.257442 0.055 Uiso 1 1 calc R U . . .
C6 C -1.0059(15) -0.4568(10) 0.2491(10) 0.049(4) Uani 1 1 d . . . . .
H6 H -0.916646 -0.478187 0.249095 0.059 Uiso 1 1 calc R U . . .
C11 C -0.918(2) -0.9977(12) -0.1010(12) 0.0761(13) Uani 1 1 d . U . . .
H11A H -0.829895 -1.024150 -0.093632 0.114 Uiso 1 1 calc R U . . .
H11B H -0.940069 -0.997370 -0.154573 0.114 Uiso 1 1 calc R U . . .
H11C H -0.987301 -1.028097 -0.073470 0.114 Uiso 1 1 calc R U . . .
C10 C -0.867(2) -0.9146(12) 0.0281(11) 0.0761(13) Uani 1 1 d . U . . .
H10A H -0.932734 -0.952675 0.050148 0.114 Uiso 1 1 calc R U . . .
H10B H -0.868871 -0.862918 0.056094 0.114 Uiso 1 1 calc R U . . .
H10C H -0.776683 -0.938445 0.030643 0.114 Uiso 1 1 calc R U . . .
O1 O -1.0820(13) -0.8683(8) -0.0599(7) 0.0721(13) Uani 1 1 d . U . . .
C15 C -1.074(2) -0.5853(12) 0.1185(12) 0.0761(13) Uani 1 1 d . U . . .
H15A H -1.118333 -0.595139 0.166881 0.114 Uiso 1 1 calc R U . . .
H15B H -1.122251 -0.541806 0.091615 0.114 Uiso 1 1 calc R U . . .
H15C H -0.980347 -0.568708 0.126861 0.114 Uiso 1 1 calc R U . . .
C0AA C -1.083(4) -0.781(3) -0.0108(17) 0.0761(13) Uani 0.500(8) 1 d D U P A 2
C18A C -1.0949(18) -0.7979(8) -0.0212(8) 0.0761(13) Uani 0.500(8) 1 d G U P A 1
C12 C -1.0401(16) -0.7251(9) -0.0478(6) 0.0761(13) Uani 1 1 d DG U . . .
H12 H -1.016823 -0.726836 -0.099476 0.091 Uiso 0.500(8) 1 calc R U P A 2
C13 C -1.0312(13) -0.6574(7) -0.0009(8) 0.0761(13) Uani 1 1 d DG U . A 2
H13 H -0.993729 -0.607646 -0.019044 0.091 Uiso 1 1 calc R U . A 2
C14 C -1.0772(14) -0.6624(7) 0.0727(7) 0.0761(13) Uani 1 1 d DG U . . .
C16 C -1.1320(14) -0.7351(8) 0.0993(6) 0.0761(13) Uani 1 1 d DG U . A 2
H16 H -1.163399 -0.738581 0.149520 0.091 Uiso 1 1 calc R U . A 2
C17 C -1.1409(16) -0.8029(7) 0.0523(8) 0.0761(13) Uani 1 1 d DG U . . .
H17 H -1.180802 -0.854295 0.063630 0.091 Uiso 1 1 calc R U . A 2


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br4 2.9493(14) . ?
Bi1 Br6 2.9434(16) . ?
Bi1 Br2 2.8095(16) . ?
Bi1 Br5 2.8937(16) . ?
Bi1 Br3 2.7810(17) . ?
Bi1 Br1 2.7743(16) . ?
S1 C11 1.77(2) . ?
S1 C10 1.781(19) . ?
S1 O1 1.758(14) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.520(19) . ?
N1 C4 1.479(18) . ?
N3 H3 0.8800 . ?
N3 C5 1.326(17) . ?
N3 C9 1.372(18) . ?
N2 C3 1.478(17) . ?
N2 C2 1.478(18) . ?
N2 C5 1.329(18) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.492(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.518(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C7 1.38(2) . ?
C8 C9 1.36(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.37(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.42(2) . ?
C9 H9 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1 C0AA 1.67(4) . ?
O1 C18A 1.348(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C14 1.50(2) . ?
C0AA C12 1.21(3) . ?
C0AA C17 1.31(2) . ?
C18A C12 1.3900 . ?
C18A C17 1.3900 . ?
C12 H12 0.9500 . ?
C12 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C14 1.3900 . ?
C14 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3900 . ?
C17 H17 0.9500 . ?

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
Br6 Bi1 Br4 83.98(4) . . ?
Br2 Bi1 Br4 88.36(5) . . ?
Br2 Bi1 Br6 86.64(5) . . ?
Br2 Bi1 Br5 173.24(6) . . ?
Br5 Bi1 Br4 85.35(5) . . ?
Br5 Bi1 Br6 95.14(4) . . ?
Br3 Bi1 Br4 90.34(5) . . ?
Br3 Bi1 Br6 172.64(5) . . ?
Br3 Bi1 Br2 88.54(5) . . ?
Br3 Bi1 Br5 89.03(5) . . ?
Br1 Bi1 Br4 177.24(5) . . ?
Br1 Bi1 Br6 94.16(5) . . ?
Br1 Bi1 Br2 93.57(5) . . ?
Br1 Bi1 Br5 92.81(5) . . ?
Br1 Bi1 Br3 91.68(5) . . ?
C11 S1 C10 99.8(9) . . ?
O1 S1 C11 103.1(8) . . ?
O1 S1 C10 101.8(9) . . ?
H1A N1 H1B 108.0 . . ?
C1 N1 H1A 109.3 . . ?
C1 N1 H1B 109.3 . . ?
C4 N1 H1A 109.3 . . ?
C4 N1 H1B 109.3 . . ?
C4 N1 C1 111.4(11) . . ?
C5 N3 H3 117.7 . . ?
C5 N3 C9 124.5(14) . . ?
C9 N3 H3 117.7 . . ?
C2 N2 C3 113.4(12) . . ?
C5 N2 C3 120.4(12) . . ?
C5 N2 C2 122.8(12) . . ?
N1 C1 H1C 109.0 . . ?
N1 C1 H1D 109.0 . . ?
N1 C1 C2 112.9(11) . . ?
H1C C1 H1D 107.8 . . ?
C2 C1 H1C 109.0 . . ?
C2 C1 H1D 109.0 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 C4 110.6(12) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
N1 C4 C3 109.0(12) . . ?
N1 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C9 C8 C7 118.2(15) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.5(15) . . ?
C6 C7 H7 119.2 . . ?
N2 C2 C1 110.9(11) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
N3 C5 N2 118.9(14) . . ?
N3 C5 C6 116.4(13) . . ?
N2 C5 C6 124.6(13) . . ?
N3 C9 H9 120.3 . . ?
C8 C9 N3 119.4(14) . . ?
C8 C9 H9 120.3 . . ?
C7 C6 C5 119.5(14) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C0AA O1 S1 105.1(16) . . ?
C18A O1 S1 110.3(11) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
C12 C0AA O1 111(2) . . ?
C12 C0AA C17 146(4) . . ?
C17 C0AA O1 103(3) . . ?
O1 C18A C12 121.2(12) . . ?
O1 C18A C17 117.6(12) . . ?
C12 C18A C17 120.0 . . ?
C0AA C12 H12 126.3 . . ?
C0AA C12 C13 107.4(19) . . ?
C13 C12 H12 126.3 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 117.2(12) . . ?
C16 C14 C15 122.6(12) . . ?
C16 C14 C13 120.0 . . ?
C14 C16 H16 120.0 . . ?
C17 C16 C14 120.0 . . ?
C17 C16 H16 120.0 . . ?
C0AA C17 C16 106(2) . . ?
C0AA C17 H17 127.1 . . ?
C16 C17 H17 127.1 . . ?

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
S1 O1 C0AA C12 72(3) . . . . ?
S1 O1 C0AA C17 -113(3) . . . . ?
S1 O1 C18A C12 63.0(14) . . . . ?
S1 O1 C18A C17 -104.6(11) . . . . ?
N1 C1 C2 N2 50.1(17) . . . . ?
N3 C5 C6 C7 0(2) . . . . ?
N2 C3 C4 N1 -58.5(16) . . . . ?
N2 C5 C6 C7 177.8(16) . . . . ?
C1 N1 C4 C3 56.7(15) . . . . ?
C3 N2 C2 C1 -52.6(17) . . . . ?
C3 N2 C5 N3 -153.1(14) . . . . ?
C3 N2 C5 C6 29(2) . . . . ?
C4 N1 C1 C2 -53.9(16) . . . . ?
C8 C7 C6 C5 -5(3) . . . . ?
C7 C8 C9 N3 1(2) . . . . ?
C2 N2 C3 C4 57.4(17) . . . . ?
C2 N2 C5 N3 5(2) . . . . ?
C2 N2 C5 C6 -173.7(15) . . . . ?
C5 N3 C9 C8 -6(2) . . . . ?
C5 N2 C3 C4 -143.0(13) . . . . ?
C5 N2 C2 C1 148.3(14) . . . . ?
C9 N3 C5 N2 -172.5(14) . . . . ?
C9 N3 C5 C6 6(2) . . . . ?
C9 C8 C7 C6 4(3) . . . . ?
C11 S1 O1 C0AA 167.8(14) . . . . ?
C11 S1 O1 C18A 168.1(12) . . . . ?
C10 S1 O1 C0AA 64.6(14) . . . . ?
C10 S1 O1 C18A 64.9(13) . . . . ?
O1 C0AA C12 C13 -174.1(17) . . . . ?
O1 C0AA C17 C16 173.8(14) . . . . ?
C15 C14 C16 C17 175.2(16) . . . . ?
C0AA C12 C13 C14 -4(3) . . . . ?
C12 C0AA C17 C16 -14(9) . . . . ?
C12 C13 C14 C15 -175.5(15) . . . . ?
C12 C13 C14 C16 0.0 . . . . ?
C13 C14 C16 C17 0.0 . . . . ?
C14 C16 C17 C0AA 4(2) . . . . ?
C17 C0AA C12 C13 14(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c18h29n3ossbbr6-p212121-forpublish
_audit_block_doi                 10.5517/ccdc.csd.cc2fbyj8
_database_code_depnum_ccdc_archive 'CCDC 2244850'
loop_
_audit_author_name
_audit_author_address
'Cao Jindong'
;University Of Science and Technology Beijing
China
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sb, C9.005 H12.227 O S, C9 H15 N3'
_chemical_formula_sum            'C18 H27.23 Br6 N3 O S Sb'
_chemical_formula_weight         934.98
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9212(3)
_cell_length_b                   16.2506(5)
_cell_length_c                   17.7298(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2858.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5824
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.441
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1765
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.991
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26578
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.405
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4562
_reflns_number_total             4994
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.871
_refine_diff_density_min         -1.641
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details 
;
 Flack x determined using 1778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.146
_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)+(0.0700P)²+5.2329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3B-H3A
 2.2 with sigma of 0.02
 H3B-H3
 2.2 with sigma of 0.02
3. Rigid bond restraints
 S1, O1
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 S1, O1, C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
S1 \\sim O1: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
S1 \\sim O1 \\sim C10 \\sim C11: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
Uanis(C15) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C17A)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(S1) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(S1) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C13) = Uanis(C12) = Uanis(C17A) = Uanis(C15)
Uanis(C13) = Uanis(C12) = Uanis(C17A) = Uanis(C18A) = Uanis(C15) = Uanis(C14)
Uanis(C18B) = Uanis(C18A) = Uanis(C15) = Uanis(C14) = Uanis(C17A) = Uanis(C12)
= Uanis(C13) = Uanis(C11) = Uanis(C10)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C17A) = Uanis(C17B) = Uanis(C16) = Uanis(C18A) = Uanis(C18B) = Uanis(C15)
= Uanis(C14) = Uanis(C13) = Uanis(C12) = Uanis(C11) = Uanis(C10)
5. Others
 1*[Sof(C17B)+Sof(H17B)]+1*[Sof(C17A)+Sof(H17A)]=1 with esd of 0.01
 1*[Sof(C18A)+Sof(H18A)+Sof(H15)]+1*[Sof(H15A)+Sof(C18B)+Sof(H18B)+Sof(H18C)]=
 1 with esd of 0.01
 1*[Sof(C17A)+Sof(H17A)]+1*[Sof(C17B)+Sof(H17B)]=0.0001 with esd of 1
 1*[Sof(C18A)+Sof(H18A)+Sof(H15)]+1*[Sof(H15A)+Sof(C18B)+Sof(H18B)+Sof(H18C)]=
 1 with esd of 0.0001
 1*[Sof(C17A)+Sof(H17A)]+1*[Sof(C17B)+Sof(H17B)]=1 with esd of 0.01
 1*[Sof(C18A)+Sof(H18A)+Sof(H15)]+1*[Sof(H15A)+Sof(C18B)+Sof(H18B)+Sof(H18C)]=
 1 with esd of 0.01
 1*[Sof(C18A)+Sof(H18A)+Sof(H15)]+1*[Sof(H15A)+Sof(C18B)+Sof(H18B)+Sof(H18C)]=
 1 with esd of 0.01
 Sof(C17B)=Sof(H17B)=FVAR(1)
 Sof(C17A)=Sof(H17A)=FVAR(2)
 Sof(C18A)=Sof(H18A)=Sof(H15)=FVAR(3)
 Sof(H15A)=Sof(C18B)=Sof(H18B)=Sof(H18C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C18B(H18B,H18C), N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,
 H4B)
6.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17A(H17A), C18A(H18A), C15(H15), C15(H15A), C14(H14), C13(H13),
 C17B(H17B), N3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
6.c Fitted hexagon refined as free rotating group:
 C17A(C18A,C15,C14,C13,C12)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Sb1 Sb -0.12107(8) -0.61003(4) -0.84477(4) 0.0332(2) Uani 1 1 d . . . . .
Br1 Br -0.12775(12) -0.77517(7) -0.91148(6) 0.0351(3) Uani 1 1 d . . . . .
Br2 Br 0.08216(12) -0.66230(8) -0.75247(7) 0.0424(3) Uani 1 1 d . . . . .
Br3 Br 0.08857(13) -0.57801(8) -0.95954(7) 0.0404(3) Uani 1 1 d . . . . .
Br4 Br -0.11325(14) -0.45633(8) -0.78843(8) 0.0470(3) Uani 1 1 d . . . . .
Br5 Br -0.34576(13) -0.57266(9) -0.94170(7) 0.0439(3) Uani 1 1 d . . . . .
Br6 Br -0.29772(13) -0.65694(8) -0.73764(8) 0.0421(3) Uani 1 1 d . . . . .
S1 S -0.0908(5) -1.1070(3) -0.9369(3) 0.0659(9) Uani 1 1 d . U . . .
O1 O 0.0847(12) -1.1379(7) -0.9467(6) 0.0682(11) Uani 1 1 d . U . . .
C10 C -0.0807(19) -1.0042(11) -0.9019(10) 0.0725(10) Uani 1 1 d . U . . .
H10A H -0.028372 -0.970352 -0.937032 0.109 Uiso 1 1 calc R U . . .
H10B H -0.036404 -1.004410 -0.852459 0.109 Uiso 1 1 calc R U . . .
H10C H -0.171688 -0.981414 -0.896869 0.109 Uiso 1 1 calc R U . . .
C11 C -0.135(2) -1.0884(11) -1.0310(10) 0.0725(10) Uani 1 1 d . U . . .
H11A H -0.224314 -1.062919 -1.032945 0.109 Uiso 1 1 calc R U . . .
H11B H -0.136302 -1.140498 -1.058746 0.109 Uiso 1 1 calc R U . . .
H11C H -0.068564 -1.051282 -1.053865 0.109 Uiso 1 1 calc R U . . .
C16 C 0.0144(18) -1.3503(12) -0.9858(11) 0.0725(10) Uani 1 1 d . . . A 2
H16 H 0.019416 -1.398465 -0.955530 0.087 Uiso 1 1 calc R U . A 2
C17A C 0.0609(17) -1.2870(9) -0.9945(6) 0.0725(10) Uani 0.45(3) 1 d G U P A -2
H17A H 0.033099 -1.304244 -0.945703 0.087 Uiso 0.45(3) 1 calc R U P A -2
C18A C 0.0598(16) -1.3424(6) -1.0542(8) 0.0725(10) Uani 0.778(4) 1 d G . P A -2
H18A H 0.031230 -1.397537 -1.046233 0.087 Uiso 0.778(4) 1 calc R U P A -2
C15 C 0.1004(13) -1.3172(6) -1.1256(6) 0.0725(10) Uani 1 1 d G U . . .
H15 H 0.099618 -1.355048 -1.166391 0.087 Uiso 0.778(4) 1 calc R U P A -2
H15A H 0.142902 -1.351103 -1.162151 0.087 Uiso 0.222(4) 1 calc R U P A 2
C14 C 0.1421(13) -1.2365(7) -1.1372(5) 0.0725(10) Uani 1 1 d G . . . .
H14 H 0.169875 -1.219270 -1.186020 0.087 Uiso 1 1 calc R U . . .
C13 C 0.1432(13) -1.1811(5) -1.0775(7) 0.0725(10) Uani 1 1 d G U . . .
H13 H 0.171744 -1.125978 -1.085492 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1026(15) -1.2063(7) -1.0061(6) 0.0725(10) Uani 1 1 d G U . . .
C17B C 0.030(3) -1.294(2) -0.940(2) 0.0725(10) Uani 0.56(3) 1 d . . P A 2
H17B H 0.011917 -1.293188 -0.887181 0.087 Uiso 0.56(3) 1 calc R U P A 2
C18B C -0.008(9) -1.384(5) -1.065(5) 0.0725(10) Uani 0.222(4) 1 d . . P A 2
H18B H -0.104432 -1.379344 -1.079340 0.087 Uiso 0.222(4) 1 calc R U P A 2
H18C H 0.019477 -1.442309 -1.067998 0.087 Uiso 0.222(4) 1 calc R U P A 2
N1 N -0.7606(10) -0.7592(7) -0.9173(6) 0.040(2) Uani 1 1 d . . . . .
H1A H -0.832030 -0.724156 -0.915249 0.048 Uiso 1 1 calc R U . . .
H1B H -0.746306 -0.772914 -0.966392 0.048 Uiso 1 1 calc R U . . .
N2 N -0.5518(10) -0.8490(6) -0.8429(6) 0.036(2) Uani 1 1 d . . . . .
N3 N -0.3322(10) -0.8650(7) -0.7916(6) 0.043(3) Uani 1 1 d . . . . .
H3 H -0.307432 -0.822135 -0.818619 0.052 Uiso 1 1 calc DR U . . .
C1 C -0.7911(12) -0.8353(8) -0.8724(7) 0.039(3) Uani 1 1 d . . . . .
H1C H -0.870077 -0.863810 -0.894261 0.047 Uiso 1 1 calc R U . . .
H1D H -0.813145 -0.819952 -0.819746 0.047 Uiso 1 1 calc R U . . .
C2 C -0.6714(12) -0.8916(8) -0.8732(8) 0.040(3) Uani 1 1 d . . . . .
H2A H -0.690791 -0.940890 -0.842252 0.048 Uiso 1 1 calc R U . . .
H2B H -0.653344 -0.909809 -0.925465 0.048 Uiso 1 1 calc R U . . .
C3 C -0.5210(12) -0.7740(7) -0.8855(7) 0.036(3) Uani 1 1 d . . . . .
H3A H -0.498411 -0.788824 -0.938152 0.043 Uiso 1 1 calc DR U . . .
H3B H -0.441408 -0.746736 -0.862961 0.043 Uiso 1 1 calc DR U . . .
C4 C -0.6350(13) -0.7168(7) -0.8854(7) 0.037(3) Uani 1 1 d . . . . .
H4A H -0.653044 -0.698019 -0.833191 0.044 Uiso 1 1 calc R U . . .
H4B H -0.612809 -0.667934 -0.916337 0.044 Uiso 1 1 calc R U . . .
C5 C -0.4629(12) -0.8894(8) -0.7994(7) 0.036(3) Uani 1 1 d . . . . .
C6 C -0.4960(14) -0.9603(9) -0.7531(9) 0.050(3) Uani 1 1 d . . . . .
H6 H -0.584958 -0.981983 -0.753194 0.060 Uiso 1 1 calc R U . . .
C7 C -0.4015(14) -0.9944(9) -0.7109(8) 0.050(3) Uani 1 1 d . . . . .
H7 H -0.424003 -1.041535 -0.681767 0.060 Uiso 1 1 calc R U . . .
C8 C -0.2684(15) -0.9637(9) -0.7072(7) 0.047(3) Uani 1 1 d . . . . .
H8 H -0.202061 -0.988986 -0.676250 0.056 Uiso 1 1 calc R U . . .
C9 C -0.2398(13) -0.8976(9) -0.7490(8) 0.047(3) Uani 1 1 d . . . . .
H9 H -0.151934 -0.874366 -0.747690 0.056 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Br1 2.9334(13) . ?
Sb1 Br2 2.7321(15) . ?
Sb1 Br3 2.9560(15) . ?
Sb1 Br4 2.6912(14) . ?
Sb1 Br5 2.8796(15) . ?
Sb1 Br6 2.6945(15) . ?
S1 O1 1.821(13) . ?
S1 C10 1.785(18) . ?
S1 C11 1.750(18) . ?
O1 C12 1.542(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17A 1.14(2) . ?
C16 C18A 1.30(2) . ?
C16 C17B 1.23(4) . ?
C16 C18B 1.52(9) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.3900 . ?
C17A C12 1.3900 . ?
C17A C17B 1.02(4) . ?
C18A H18A 0.9500 . ?
C18A C15 1.3900 . ?
C18A C18B 0.97(9) . ?
C15 H15 0.9500 . ?
C15 H15A 0.9500 . ?
C15 C14 1.3900 . ?
C15 C18B 1.87(9) . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C12 1.3900 . ?
C12 C17B 1.99(4) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9900 . ?
C18B H18C 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.501(17) . ?
N1 C4 1.532(16) . ?
N2 C2 1.475(15) . ?
N2 C3 1.465(15) . ?
N2 C5 1.343(15) . ?
N3 H3 0.8800 . ?
N3 C5 1.362(16) . ?
N3 C9 1.300(16) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.499(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.464(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.453(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.32(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.41(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.34(2) . ?
C9 H9 0.9500 . ?

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
Br1 Sb1 Br3 84.23(4) . . ?
Br2 Sb1 Br1 88.50(4) . . ?
Br2 Sb1 Br3 87.01(4) . . ?
Br2 Sb1 Br5 173.91(5) . . ?
Br4 Sb1 Br1 177.98(5) . . ?
Br4 Sb1 Br2 92.57(5) . . ?
Br4 Sb1 Br3 94.12(4) . . ?
Br4 Sb1 Br5 92.76(5) . . ?
Br4 Sb1 Br6 91.12(5) . . ?
Br5 Sb1 Br1 86.26(4) . . ?
Br5 Sb1 Br3 95.55(4) . . ?
Br6 Sb1 Br1 90.62(4) . . ?
Br6 Sb1 Br2 88.27(4) . . ?
Br6 Sb1 Br3 173.10(5) . . ?
Br6 Sb1 Br5 88.67(5) . . ?
C10 S1 O1 103.8(8) . . ?
C11 S1 O1 101.3(8) . . ?
C11 S1 C10 100.6(8) . . ?
C12 O1 S1 112.0(9) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17A C16 H16 143.2 . . ?
C17A C16 C18A 69.1(11) . . ?
C17A C16 C17B 51.0(19) . . ?
C17A C16 C18B 105(4) . . ?
C18A C16 H16 126.1 . . ?
C18A C16 C18B 39(3) . . ?
C17B C16 H16 103.3 . . ?
C17B C16 C18A 120(2) . . ?
C17B C16 C18B 153(4) . . ?
C18B C16 H16 103.3 . . ?
C16 C17A H17A 59.5 . . ?
C16 C17A C18A 61.0(13) . . ?
C16 C17A C12 173.4(16) . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C12 120.0 . . ?
C12 C17A H17A 120.0 . . ?
C17B C17A C16 69(2) . . ?
C17B C17A H17A 10.6 . . ?
C17B C17A C18A 130(2) . . ?
C17B C17A C12 110(2) . . ?
C16 C18A C17A 49.9(11) . . ?
C16 C18A H18A 70.4 . . ?
C16 C18A C15 168.2(12) . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C15 120.0 . . ?
C15 C18A H18A 120.0 . . ?
C18B C18A C16 82(5) . . ?
C18B C18A C17A 127(5) . . ?
C18B C18A H18A 33.6 . . ?
C18B C18A C15 103(5) . . ?
C18A C15 H15 120.0 . . ?
C18A C15 H15A 125.4 . . ?
C18A C15 C18B 30(3) . . ?
H15 C15 H15A 26.8 . . ?
C14 C15 C18A 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 H15A 108.3 . . ?
C14 C15 C18B 143(3) . . ?
C18B C15 H15 93.4 . . ?
C18B C15 H15A 108.3 . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
O1 C12 C17B 94.1(12) . . ?
C17A C12 O1 122.9(9) . . ?
C17A C12 C17B 29.0(12) . . ?
C13 C12 O1 116.3(9) . . ?
C13 C12 C17A 120.0 . . ?
C13 C12 C17B 149.0(12) . . ?
C16 C17B C12 101(2) . . ?
C16 C17B H17B 129.6 . . ?
C17A C17B C16 60(2) . . ?
C17A C17B C12 41.2(15) . . ?
C17A C17B H17B 169.9 . . ?
C12 C17B H17B 129.6 . . ?
C16 C18B C15 104(5) . . ?
C16 C18B H18B 111.0 . . ?
C16 C18B H18C 111.0 . . ?
C18A C18B C16 58(4) . . ?
C18A C18B C15 46(4) . . ?
C18A C18B H18B 131.8 . . ?
C18A C18B H18C 118.7 . . ?
C15 C18B H18B 111.0 . . ?
C15 C18B H18C 111.0 . . ?
H18B C18B H18C 109.0 . . ?
H1A N1 H1B 108.2 . . ?
C1 N1 H1A 109.7 . . ?
C1 N1 H1B 109.7 . . ?
C1 N1 C4 109.8(9) . . ?
C4 N1 H1A 109.7 . . ?
C4 N1 H1B 109.7 . . ?
C3 N2 C2 111.7(9) . . ?
C5 N2 C2 120.6(10) . . ?
C5 N2 C3 124.4(10) . . ?
C5 N3 H3 116.2 . . ?
C5 N3 C9 127.7(12) . . ?
C9 N3 H3 116.2 . . ?
N1 C1 H1C 109.7 . . ?
N1 C1 H1D 109.7 . . ?
N1 C1 C2 109.7(10) . . ?
H1C C1 H1D 108.2 . . ?
C2 C1 H1C 109.7 . . ?
C2 C1 H1D 109.7 . . ?
N2 C2 C1 110.4(10) . . ?
N2 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
N2 C3 C4 111.5(10) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N1 C4 C3 110.0(9) . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C6 124.3(11) . . ?
N3 C5 N2 122.7(11) . . ?
N3 C5 C6 112.9(11) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(13) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 118.6 . . ?
C6 C7 C8 122.8(13) . . ?
C8 C7 H7 118.6 . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.2(13) . . ?
C9 C8 H8 121.4 . . ?
N3 C9 H9 120.0 . . ?
C8 C9 N3 120.0(13) . . ?
C8 C9 H9 120.0 . . ?

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
S1 O1 C12 C17A -71.9(10) . . . . ?
S1 O1 C12 C13 98.0(10) . . . . ?
S1 O1 C12 C17B -75.5(12) . . . . ?
C10 S1 O1 C12 -155.1(9) . . . . ?
C11 S1 O1 C12 -51.1(10) . . . . ?
C16 C17A C18A C15 172.5(18) . . . . ?
C16 C17A C18A C18B 32(6) . . . . ?
C16 C17A C17B C12 -173.0(17) . . . . ?
C16 C18A C15 C14 29(7) . . . . ?
C16 C18A C15 C18B -119(9) . . . . ?
C16 C18A C18B C15 169.6(16) . . . . ?
C17A C16 C18A C15 -34(7) . . . . ?
C17A C16 C18A C18B -154(5) . . . . ?
C17A C16 C17B C12 4.7(11) . . . . ?
C17A C16 C18B C18A 25(5) . . . . ?
C17A C16 C18B C15 17(5) . . . . ?
C17A C18A C15 C14 0.0 . . . . ?
C17A C18A C15 C18B -148(6) . . . . ?
C17A C18A C18B C16 -24(4) . . . . ?
C17A C18A C18B C15 145(5) . . . . ?
C18A C16 C17A C17B -177(2) . . . . ?
C18A C16 C17B C17A 3(2) . . . . ?
C18A C16 C17B C12 8(3) . . . . ?
C18A C16 C18B C15 -7.7(13) . . . . ?
C18A C17A C12 O1 169.6(12) . . . . ?
C18A C17A C12 C13 0.0 . . . . ?
C18A C17A C12 C17B 177(3) . . . . ?
C18A C17A C17B C16 -4(3) . . . . ?
C18A C17A C17B C12 -177(3) . . . . ?
C18A C15 C14 C13 0.0 . . . . ?
C18A C15 C18B C16 9.1(16) . . . . ?
C15 C18A C18B C16 -169.6(16) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C14 C15 C18B C16 -41(7) . . . . ?
C14 C15 C18B C18A -50(8) . . . . ?
C14 C13 C12 O1 -170.3(12) . . . . ?
C14 C13 C12 C17A 0.0 . . . . ?
C14 C13 C12 C17B -3(2) . . . . ?
C12 C17A C18A C16 -172.5(18) . . . . ?
C12 C17A C18A C15 0.0 . . . . ?
C12 C17A C18A C18B -140(6) . . . . ?
C12 C17A C17B C16 173.0(17) . . . . ?
C17B C16 C17A C18A 177(2) . . . . ?
C17B C16 C18A C17A -3(2) . . . . ?
C17B C16 C18A C15 -36(8) . . . . ?
C17B C16 C18A C18B -157(6) . . . . ?
C17B C16 C18B C18A 48(11) . . . . ?
C17B C16 C18B C15 41(11) . . . . ?
C17B C17A C18A C16 4(3) . . . . ?
C17B C17A C18A C15 176(3) . . . . ?
C17B C17A C18A C18B 36(7) . . . . ?
C17B C17A C12 O1 -7(2) . . . . ?
C17B C17A C12 C13 -177(3) . . . . ?
C18B C16 C17A C18A -16(3) . . . . ?
C18B C16 C17A C17B 167(4) . . . . ?
C18B C16 C18A C17A 154(5) . . . . ?
C18B C16 C18A C15 121(9) . . . . ?
C18B C16 C17B C17A -30(9) . . . . ?
C18B C16 C17B C12 -25(9) . . . . ?
C18B C18A C15 C14 148(6) . . . . ?
C18B C15 C14 C13 27(4) . . . . ?
N1 C1 C2 N2 57.6(14) . . . . ?
N2 C3 C4 N1 -56.8(13) . . . . ?
N2 C5 C6 C7 -178.4(14) . . . . ?
N3 C5 C6 C7 -1(2) . . . . ?
C1 N1 C4 C3 57.0(12) . . . . ?
C2 N2 C3 C4 57.9(14) . . . . ?
C2 N2 C5 N3 156.5(12) . . . . ?
C2 N2 C5 C6 -26.7(19) . . . . ?
C3 N2 C2 C1 -57.6(14) . . . . ?
C3 N2 C5 N3 -1.4(19) . . . . ?
C3 N2 C5 C6 175.5(13) . . . . ?
C4 N1 C1 C2 -57.2(12) . . . . ?
C5 N2 C2 C1 141.9(11) . . . . ?
C5 N2 C3 C4 -142.5(12) . . . . ?
C5 N3 C9 C8 1(2) . . . . ?
C5 C6 C7 C8 1(2) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C7 C8 C9 N3 -1(2) . . . . ?
C9 N3 C5 N2 177.2(13) . . . . ?
C9 N3 C5 C6 0(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
