# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_mo_xm3_174_4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2456325'
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan University
China
;
_audit_update_record             
;
2025-07-09 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;
_audit_creation_date             2025-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br8 Sb2, 2(C6 H6 N O2), H2 O'
_chemical_formula_sum            'C12 H14 Br8 N2 O5 Sb2'
_chemical_formula_weight         1149.03
_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'
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      triclinic
_space_group_IT_number           2
_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                   11.9799(3)
_cell_length_b                   12.1232(3)
_cell_length_c                   12.1910(4)
_cell_angle_alpha                100.8220(10)
_cell_angle_beta                 109.3480(10)
_cell_angle_gamma                116.8420(10)
_cell_volume                     1365.66(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    302.0
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.499
_shelx_estimated_absorpt_T_min   0.134
_exptl_absorpt_coefficient_mu    13.706
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1496 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.3778. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37041
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      302.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4780
_reflns_number_total             6265
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.341
_refine_diff_density_min         -2.029
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.025
_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)+(0.0672P)²+6.9584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), N2(H2A), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.77987(5) 0.84689(5) 0.35427(5) 0.03881(15) Uani 1 1 d . . . . .
Sb2 Sb 0.97383(5) 0.76473(5) 0.69495(5) 0.04231(15) Uani 1 1 d . . . . .
Br1 Br 0.71495(11) 1.01669(11) 0.30181(13) 0.0735(3) Uani 1 1 d . . . . .
Br2 Br 0.66175(14) 0.68982(14) 0.12098(10) 0.0824(4) Uani 1 1 d . . . . .
Br3 Br 0.54969(10) 0.70294(10) 0.36090(10) 0.0656(3) Uani 1 1 d . . . . .
Br4 Br 0.87826(13) 0.66553(11) 0.41407(12) 0.0741(3) Uani 1 1 d . . . . .
Br5 Br 0.92323(10) 0.98731(9) 0.65471(9) 0.0549(2) Uani 1 1 d . . . . .
Br6 Br 1.03558(12) 0.84722(11) 0.93390(10) 0.0758(3) Uani 1 1 d . . . . .
Br7 Br 1.04253(15) 0.59162(12) 0.70603(13) 0.0811(3) Uani 1 1 d . . . . .
Br8 Br 0.71843(11) 0.59455(10) 0.63126(10) 0.0695(3) Uani 1 1 d . . . . .
O1 O 0.6119(7) 1.0074(6) 0.6282(6) 0.0587(15) Uani 1 1 d . . . . .
O2 O 0.3890(7) 0.8328(7) 0.4951(7) 0.0648(17) Uani 1 1 d . . . . .
H2 H 0.395924 0.871638 0.447031 0.097 Uiso 1 1 calc GR . . . .
N1 N 0.4201(10) 0.6110(8) 0.7004(9) 0.076(3) Uani 1 1 d . . . . .
H1 H 0.346900 0.532288 0.677512 0.091 Uiso 1 1 calc R . . . .
C1 C 0.5125(9) 0.8941(8) 0.5951(8) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.5225(9) 0.8101(8) 0.6678(8) 0.0504(19) Uani 1 1 d . . . . .
C3 C 0.6483(10) 0.8561(8) 0.7712(9) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.728205 0.940613 0.795761 0.063 Uiso 1 1 calc R . . . .
C4 C 0.6577(11) 0.7783(11) 0.8392(10) 0.065(2) Uani 1 1 d . . . . .
H4 H 0.742513 0.810499 0.910084 0.078 Uiso 1 1 calc R . . . .
C5 C 0.5389(13) 0.6523(10) 0.7999(9) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.542623 0.597257 0.842923 0.082 Uiso 1 1 calc R . . . .
C6 C 0.4049(11) 0.6834(9) 0.6315(9) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.318163 0.649189 0.562024 0.075 Uiso 1 1 calc R . . . .
O3 O 0.4042(7) 0.9494(6) 0.0712(7) 0.0581(15) Uani 1 1 d . . . . .
O4 O 0.4407(8) 0.8241(7) -0.0530(7) 0.0625(16) Uani 1 1 d . . . . .
H4A H 0.461692 0.884191 -0.079292 0.094 Uiso 1 1 calc GR . . . .
N2 N 0.1846(8) 0.6372(7) 0.1527(7) 0.0528(17) Uani 1 1 d . . . . .
H2A H 0.152330 0.650011 0.203845 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3897(8) 0.8425(9) 0.0200(8) 0.0492(19) Uani 1 1 d . . . . .
C8 C 0.3093(8) 0.7223(8) 0.0459(7) 0.0438(17) Uani 1 1 d . . . . .
C9 C 0.2856(10) 0.5989(9) -0.0078(9) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.321223 0.585832 -0.062661 0.064 Uiso 1 1 calc R . . . .
C10 C 0.2076(11) 0.4931(10) 0.0207(10) 0.062(2) Uani 1 1 d . . . . .
H10 H 0.188258 0.408001 -0.016971 0.074 Uiso 1 1 calc R . . . .
C11 C 0.1598(10) 0.5153(9) 0.1041(9) 0.056(2) Uani 1 1 d . . . . .
H11 H 0.110791 0.446774 0.126797 0.067 Uiso 1 1 calc R . . . .
C12 C 0.2551(9) 0.7372(8) 0.1267(8) 0.0483(18) Uani 1 1 d . . . . .
H12 H 0.269050 0.820066 0.163117 0.058 Uiso 1 1 calc R . . . .
O5 O 0.0862(9) 0.7318(7) 0.2824(8) 0.087(3) Uani 1 1 d . . . . .
H5A H 0.011560 0.692753 0.290151 0.130 Uiso 1 1 d R . . . .
H5B H 0.103740 0.810013 0.291171 0.130 Uiso 1 1 d R . . . .


_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 2.6196(11) . ?
Sb1 Br2 2.5658(12) . ?
Sb1 Br3 2.5516(10) . ?
Sb1 Br4 3.0212(12) . ?
Sb1 Br5 3.1800(11) . ?
Sb2 Br4 3.0158(14) . ?
Sb2 Br5 3.1091(10) . ?
Sb2 Br6 2.6161(12) . ?
Sb2 Br7 2.5870(11) . ?
Sb2 Br8 2.5189(11) . ?
O1 C1 1.210(10) . ?
O2 H2 0.8200 . ?
O2 C1 1.304(11) . ?
N1 H1 0.8600 . ?
N1 C5 1.316(14) . ?
N1 C6 1.352(13) . ?
C1 C2 1.488(13) . ?
C2 C3 1.375(13) . ?
C2 C6 1.385(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(14) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O3 C7 1.233(10) . ?
O4 H4A 0.8200 . ?
O4 C7 1.274(10) . ?
N2 H2A 0.8600 . ?
N2 C11 1.334(11) . ?
N2 C12 1.297(10) . ?
C7 C8 1.502(11) . ?
C8 C9 1.369(11) . ?
C8 C12 1.375(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O5 H5A 0.8503 . ?
O5 H5B 0.8498 . ?

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 Br4 175.06(4) . . ?
Br1 Sb1 Br5 97.42(4) . . ?
Br2 Sb1 Br1 94.40(4) . . ?
Br2 Sb1 Br4 85.61(4) . . ?
Br2 Sb1 Br5 167.64(4) . . ?
Br3 Sb1 Br1 93.03(4) . . ?
Br3 Sb1 Br2 89.60(4) . . ?
Br3 Sb1 Br4 91.91(4) . . ?
Br3 Sb1 Br5 86.21(3) . . ?
Br4 Sb1 Br5 82.92(3) . . ?
Br4 Sb2 Br5 84.22(3) . . ?
Br6 Sb2 Br4 175.15(4) . . ?
Br6 Sb2 Br5 93.42(3) . . ?
Br7 Sb2 Br4 88.92(4) . . ?
Br7 Sb2 Br5 169.41(4) . . ?
Br7 Sb2 Br6 94.00(4) . . ?
Br8 Sb2 Br4 85.11(4) . . ?
Br8 Sb2 Br5 94.53(4) . . ?
Br8 Sb2 Br6 90.87(4) . . ?
Br8 Sb2 Br7 92.91(4) . . ?
Sb2 Br4 Sb1 98.41(3) . . ?
Sb1 Br5 Sb1 85.76(3) . 2_776 ?
Sb2 Br5 Sb1 91.89(3) . 2_776 ?
Sb2 Br5 Sb1 93.22(3) . . ?
C1 O2 H2 109.5 . . ?
C5 N1 H1 117.6 . . ?
C5 N1 C6 124.7(9) . . ?
C6 N1 H1 117.6 . . ?
O1 C1 O2 125.2(9) . . ?
O1 C1 C2 121.5(8) . . ?
O2 C1 C2 113.3(8) . . ?
C3 C2 C1 120.8(8) . . ?
C3 C2 C6 118.8(8) . . ?
C6 C2 C1 120.4(9) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(9) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.7(10) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 118.9(10) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C2 117.9(9) . . ?
N1 C6 H6 121.0 . . ?
C2 C6 H6 121.0 . . ?
C7 O4 H4A 109.5 . . ?
C11 N2 H2A 118.4 . . ?
C12 N2 H2A 118.4 . . ?
C12 N2 C11 123.2(8) . . ?
O3 C7 O4 125.5(8) . . ?
O3 C7 C8 119.2(7) . . ?
O4 C7 C8 115.3(8) . . ?
C9 C8 C7 123.7(7) . . ?
C9 C8 C12 118.4(8) . . ?
C12 C8 C7 117.9(7) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(8) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(9) . . ?
C11 C10 H10 120.3 . . ?
N2 C11 C10 118.8(8) . . ?
N2 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N2 C12 C8 120.8(8) . . ?
N2 C12 H12 119.6 . . ?
C8 C12 H12 119.6 . . ?
H5A O5 H5B 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 1.89 2.668(9) 157.8 2_676 yes
N1 H1 Br4 0.86 2.33 3.175(8) 167.2 2_666 yes
O4 H4A O3 0.82 1.89 2.634(9) 151.2 2_675 yes
N2 H2A O5 0.86 1.84 2.642(10) 154.6 . yes
O5 H5A Br4 0.85 2.50 3.279(7) 152.7 1_455 yes
O5 H5B Br5 0.85 2.61 3.409(7) 156.5 2_676 yes

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
O1 C1 C2 C3 -3.9(12) . . . . ?
O1 C1 C2 C6 176.6(8) . . . . ?
O2 C1 C2 C3 175.7(8) . . . . ?
O2 C1 C2 C6 -3.7(11) . . . . ?
C1 C2 C3 C4 179.8(8) . . . . ?
C1 C2 C6 N1 179.5(8) . . . . ?
C2 C3 C4 C5 1.3(13) . . . . ?
C3 C2 C6 N1 0.0(13) . . . . ?
C3 C4 C5 N1 -1.1(14) . . . . ?
C5 N1 C6 C2 0.1(15) . . . . ?
C6 N1 C5 C4 0.4(16) . . . . ?
C6 C2 C3 C4 -0.7(13) . . . . ?
O3 C7 C8 C9 179.0(8) . . . . ?
O3 C7 C8 C12 -0.1(12) . . . . ?
O4 C7 C8 C9 -2.6(12) . . . . ?
O4 C7 C8 C12 178.3(8) . . . . ?
C7 C8 C9 C10 -178.9(8) . . . . ?
C7 C8 C12 N2 180.0(7) . . . . ?
C8 C9 C10 C11 -1.9(14) . . . . ?
C9 C8 C12 N2 0.9(12) . . . . ?
C9 C10 C11 N2 2.6(14) . . . . ?
C11 N2 C12 C8 -0.2(13) . . . . ?
C12 N2 C11 C10 -1.6(14) . . . . ?
C12 C8 C9 C10 0.2(13) . . . . ?


_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_mo_xm3_174_6_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2456326'
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan University
China
;
_audit_update_record             
;
2025-06-04 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;
_audit_creation_date             2025-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br5 Sb, 2(C6 H6 N O2)'
_chemical_formula_sum            'C12 H12 Br5 N2 O4 Sb'
_chemical_formula_weight         769.54
_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'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.0673(8)
_cell_length_b                   19.4421(8)
_cell_length_c                   8.0411(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.518(3)
_cell_angle_gamma                90
_cell_volume                     2175.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5808
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.679
_shelx_estimated_absorpt_T_min   0.110
_exptl_absorpt_coefficient_mu    10.471
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1789 before and 0.1033 after correction. The Ratio of minimum to maximum transmission is 0.2889. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16823
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_temperature      302.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                3549
_reflns_number_total             4205
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.496
_refine_diff_density_min         -1.307
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.009
_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)+(0.0626P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.63(2)
 0.37(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), N1(H1), C5(H5), C4(H4), C3(H3), C9(H9), C12(H12), N2(H2A), C11(H11),
 C10(H10)
3.b Fitted hexagon refined as free rotating group:
 C2(C6,N1,C5,C4,C3), C9(C8,C12,N2,C11,C10)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.50052(7) 0.12171(3) 0.34721(12) 0.0408(2) Uani 1 1 d . . . . .
Br1 Br 0.51149(13) 0.00806(8) 0.0768(2) 0.0563(4) Uani 1 1 d . . . . .
Br2 Br 0.49063(13) 0.22089(8) 0.1251(2) 0.0580(4) Uani 1 1 d . . . . .
Br3 Br 0.51016(13) 0.20736(9) 0.6001(2) 0.0599(5) Uani 1 1 d . . . . .
Br4 Br 0.30938(13) 0.12231(8) 0.3253(3) 0.0648(5) Uani 1 1 d . . . . .
Br5 Br 0.70909(13) 0.13401(8) 0.3684(2) 0.0616(5) Uani 1 1 d . . . . .
O1 O 0.3888(10) 0.5163(7) 0.172(2) 0.090(5) Uani 1 1 d . . . . .
O2 O 0.4683(9) 0.4189(7) 0.1510(19) 0.078(4) Uani 1 1 d . . . . .
H2 H 0.518915 0.439982 0.175711 0.118 Uiso 1 1 calc GR . . . .
C1 C 0.4001(12) 0.4534(9) 0.195(3) 0.064(5) Uani 1 1 d . . . . .
C2 C 0.3296(6) 0.4163(5) 0.2741(14) 0.052(4) Uani 1 1 d . . . . .
C6 C 0.2503(7) 0.4529(4) 0.3103(15) 0.060(4) Uani 1 1 d G . . . .
H6 H 0.244355 0.499451 0.284508 0.072 Uiso 1 1 calc R . . . .
N1 N 0.1798(6) 0.4199(5) 0.3850(16) 0.068(4) Uani 1 1 d G . . . .
H1 H 0.130749 0.442509 0.407443 0.081 Uiso 1 1 calc R . . . .
C5 C 0.1887(8) 0.3502(5) 0.4236(17) 0.065(5) Uani 1 1 d G . . . .
H5 H 0.141527 0.328159 0.473615 0.078 Uiso 1 1 calc R . . . .
C4 C 0.2680(9) 0.3136(4) 0.3874(16) 0.074(6) Uani 1 1 d G . . . .
H4 H 0.273900 0.267063 0.413206 0.089 Uiso 1 1 calc R . . . .
C3 C 0.3384(7) 0.3467(5) 0.3127(15) 0.060(4) Uani 1 1 d G . . . .
H3 H 0.391502 0.322161 0.288448 0.072 Uiso 1 1 calc R . . . .
O3 O 0.6002(11) 0.5111(6) 0.510(2) 0.093(5) Uani 1 1 d . . . . .
O4 O 0.5288(11) 0.4140(8) 0.563(3) 0.101(5) Uani 1 1 d . . . . .
H4A H 0.503433 0.437721 0.628120 0.152 Uiso 1 1 calc GR . . . .
C7 C 0.5935(13) 0.4479(8) 0.509(2) 0.062(4) Uani 1 1 d . . . . .
C9 C 0.7444(7) 0.4409(4) 0.3729(15) 0.063(4) Uani 1 1 d . . . . .
H9 H 0.750837 0.488539 0.376642 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6680(7) 0.4097(4) 0.4351(15) 0.049(3) Uani 1 1 d G . . . .
C12 C 0.6584(7) 0.3385(5) 0.4294(15) 0.067(5) Uani 1 1 d G . . . .
H12 H 0.607323 0.317638 0.471099 0.080 Uiso 1 1 calc R . . . .
N2 N 0.7251(8) 0.2986(4) 0.3615(15) 0.069(4) Uani 1 1 d G . . . .
H2A H 0.719122 0.254620 0.358028 0.082 Uiso 1 1 calc R . . . .
C11 C 0.8014(7) 0.3299(5) 0.2993(16) 0.073(5) Uani 1 1 d G . . . .
H11 H 0.846051 0.303186 0.253835 0.088 Uiso 1 1 calc R . . . .
C10 C 0.8111(7) 0.4010(5) 0.3049(17) 0.064(5) Uani 1 1 d G . . . .
H10 H 0.862153 0.421937 0.263284 0.077 Uiso 1 1 calc R . . . .


_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 3.1200(19) . ?
Sb1 Br2 2.6181(18) . ?
Sb1 Br3 2.6161(18) . ?
Sb1 Br4 2.6685(19) . ?
Sb1 Br5 2.923(2) . ?
O1 C1 1.244(19) . ?
O2 C1 1.26(2) . ?
C1 C2 1.446(19) . ?
C2 C6 1.3900 . ?
C2 C3 1.3900 . ?
C6 N1 1.3900 . ?
N1 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
O3 C7 1.233(18) . ?
O4 C7 1.25(2) . ?
C7 C8 1.478(19) . ?
C9 C8 1.3900 . ?
C9 C10 1.3900 . ?
C8 C12 1.3900 . ?
C12 N2 1.3900 . ?
N2 C11 1.3900 . ?
C11 C10 1.3900 . ?

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
Br2 Sb1 Br1 92.82(6) . . ?
Br2 Sb1 Br4 90.03(6) . . ?
Br2 Sb1 Br5 86.04(6) . . ?
Br3 Sb1 Br1 172.01(8) . . ?
Br3 Sb1 Br2 93.02(6) . . ?
Br3 Sb1 Br4 89.10(6) . . ?
Br3 Sb1 Br5 88.08(6) . . ?
Br4 Sb1 Br1 96.34(6) . . ?
Br4 Sb1 Br5 175.03(5) . . ?
Br5 Sb1 Br1 86.89(5) . . ?
O1 C1 O2 124.3(17) . . ?
O1 C1 C2 118.5(15) . . ?
O2 C1 C2 117.2(14) . . ?
C6 C2 C1 117.4(9) . . ?
C6 C2 C3 120.0 . . ?
C3 C2 C1 122.6(9) . . ?
N1 C6 C2 120.0 . . ?
C6 N1 C5 120.0 . . ?
N1 C5 C4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C4 C3 C2 120.0 . . ?
O3 C7 O4 125.5(18) . . ?
O3 C7 C8 116.6(16) . . ?
O4 C7 C8 118.0(15) . . ?
C8 C9 C10 120.0 . . ?
C9 C8 C7 123.8(9) . . ?
C9 C8 C12 120.0 . . ?
C12 C8 C7 116.2(9) . . ?
N2 C12 C8 120.0 . . ?
C12 N2 C11 120.0 . . ?
C10 C11 N2 120.0 . . ?
C11 C10 C9 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 2.11 2.684(18) 127.3 2_564 yes
N1 H1 Br1 0.86 2.50 3.321(8) 159.0 4_455 yes
O4 H4A O1 0.82 1.92 2.645(19) 146.7 2_565 yes
N2 H2A Br5 0.86 2.35 3.210(7) 175.8 . yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.63(2)
2 0.37(2)

