# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_110K
_database_code_depnum_ccdc_archive 'CCDC 2083460'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 In, 3(C2 H8 N)'
_chemical_formula_sum            'C6 H24 Br6 In N3'
_chemical_formula_weight         732.56
_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'
In In -0.7276 1.3100 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   22.5327(14)
_cell_length_b                   7.8741(6)
_cell_length_c                   23.2252(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.655(2)
_cell_angle_gamma                90
_cell_volume                     3967.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7670
_cell_measurement_temperature    110
_cell_measurement_theta_max      28.477
_cell_measurement_theta_min      2.752
_shelx_estimated_absorpt_T_max   0.351
_shelx_estimated_absorpt_T_min   0.299
_exptl_absorpt_coefficient_mu    13.261
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1454 before and 0.0932 after correction.
The Ratio of minimum to maximum transmission is 0.4791.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.484
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4226
_reflns_number_total             5000
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       Bruker
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.260
_refine_diff_density_min         -1.677
_refine_diff_density_rms         0.293
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         5000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.7544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1074
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2C,H2D,H2E), N3(H3D,H3E,H3F), C5(H5A,H5B,H5C), C1(H1D,
 H1E,H1F), C3(H3A,H3B,H3C)
;
_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
In1 In 0.33481(2) 0.52164(4) 0.64418(2) 0.01286(10) Uani 1 1 d . . . . .
Br1 Br 0.42493(2) 0.29250(6) 0.67897(2) 0.01676(12) Uani 1 1 d . . . . .
Br5 Br 0.25275(2) 0.27288(6) 0.60575(2) 0.01653(12) Uani 1 1 d . . . . .
Br2 Br 0.41767(2) 0.77064(6) 0.68796(2) 0.01669(12) Uani 1 1 d . . . . .
Br6 Br 0.31734(2) 0.48265(6) 0.75551(2) 0.01635(12) Uani 1 1 d . . . . .
Br4 Br 0.24644(2) 0.75260(6) 0.61899(2) 0.01585(12) Uani 1 1 d . . . . .
Br3 Br 0.35513(2) 0.55335(7) 0.53793(2) 0.01912(12) Uani 1 1 d . . . . .
N1 N 0.3069(2) 0.9768(6) 0.51878(19) 0.0206(9) Uani 1 1 d . . . . .
H1A H 0.284013 1.037586 0.487207 0.025 Uiso 1 1 calc R U . . .
H1B H 0.288878 0.981785 0.549434 0.025 Uiso 1 1 calc R U . . .
H1C H 0.309002 0.866694 0.507608 0.025 Uiso 1 1 calc R U . . .
N2 N 0.46192(19) 0.5515(6) 0.82685(19) 0.0206(9) Uani 1 1 d . . . . .
H2C H 0.423158 0.525259 0.804672 0.025 Uiso 1 1 calc R U . . .
H2D H 0.487007 0.460079 0.828292 0.025 Uiso 1 1 calc R U . . .
H2E H 0.476507 0.640733 0.809848 0.025 Uiso 1 1 calc R U . . .
N3 N 0.17426(19) 0.5444(6) 0.76593(18) 0.0204(9) Uani 1 1 d . . . . .
H3D H 0.173877 0.659913 0.767057 0.024 Uiso 1 1 calc R U . . .
H3E H 0.213573 0.506428 0.780744 0.024 Uiso 1 1 calc R U . . .
H3F H 0.150231 0.502610 0.788465 0.024 Uiso 1 1 calc R U . . .
C5 C 0.0842(3) 0.5483(8) 0.6781(3) 0.0302(13) Uani 1 1 d . . . . .
H5A H 0.070104 0.519229 0.635537 0.045 Uiso 1 1 calc R U . . .
H5B H 0.082806 0.671765 0.682825 0.045 Uiso 1 1 calc R U . . .
H5C H 0.057424 0.493821 0.699548 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3699(3) 1.0491(8) 0.5385(3) 0.0293(13) Uani 1 1 d . . . . .
H2A H 0.367220 1.172956 0.544678 0.035 Uiso 1 1 calc R U . . .
H2B H 0.392185 0.997541 0.577189 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1500(3) 0.4863(7) 0.7034(2) 0.0255(12) Uani 1 1 d . . . . .
H6A H 0.151011 0.360732 0.702002 0.031 Uiso 1 1 calc R U . . .
H6B H 0.176312 0.530765 0.678891 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4048(3) 1.0178(9) 0.4941(3) 0.0433(18) Uani 1 1 d . . . . .
H1D H 0.382744 1.068237 0.455692 0.065 Uiso 1 1 calc R U . . .
H1E H 0.408961 0.895137 0.489087 0.065 Uiso 1 1 calc R U . . .
H1F H 0.445798 1.069104 0.507949 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4463(4) 0.4478(10) 0.9206(3) 0.050(2) Uani 1 1 d . . . . .
H3A H 0.407056 0.397984 0.898058 0.076 Uiso 1 1 calc R U . . .
H3B H 0.443249 0.483030 0.960195 0.076 Uiso 1 1 calc R U . . .
H3C H 0.479206 0.363424 0.925165 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4605(3) 0.5974(9) 0.8881(3) 0.0361(15) Uani 1 1 d . . . . .
H4A H 0.428833 0.686029 0.886148 0.043 Uiso 1 1 calc R U . . .
H4B H 0.500934 0.644771 0.910049 0.043 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
In1 Br1 2.6734(6) . ?
In1 Br5 2.6761(6) . ?
In1 Br2 2.7092(6) . ?
In1 Br6 2.7356(6) . ?
In1 Br4 2.6430(6) . ?
In1 Br3 2.6404(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.484(7) . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
N2 H2E 0.9100 . ?
N2 C4 1.476(7) . ?
N3 H3D 0.9100 . ?
N3 H3E 0.9100 . ?
N3 H3F 0.9100 . ?
N3 C6 1.479(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C6 1.520(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.477(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.480(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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 In1 Br5 90.397(19) . . ?
Br1 In1 Br2 89.117(18) . . ?
Br1 In1 Br6 85.981(17) . . ?
Br5 In1 Br2 177.531(19) . . ?
Br5 In1 Br6 88.305(17) . . ?
Br2 In1 Br6 89.246(17) . . ?
Br4 In1 Br1 175.388(19) . . ?
Br4 In1 Br5 91.055(19) . . ?
Br4 In1 Br2 89.247(18) . . ?
Br4 In1 Br6 89.687(17) . . ?
Br3 In1 Br1 92.127(18) . . ?
Br3 In1 Br5 92.060(18) . . ?
Br3 In1 Br2 90.377(18) . . ?
Br3 In1 Br6 178.08(2) . . ?
Br3 In1 Br4 92.195(18) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H2C N2 H2D 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C4 N2 H2C 109.5 . . ?
C4 N2 H2D 109.5 . . ?
C4 N2 H2E 109.5 . . ?
H3D N3 H3E 109.5 . . ?
H3D N3 H3F 109.5 . . ?
H3E N3 H3F 109.5 . . ?
C6 N3 H3D 109.5 . . ?
C6 N3 H3E 109.5 . . ?
C6 N3 H3F 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 N1 111.5(5) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
N3 C6 C5 110.1(4) . . ?
N3 C6 H6A 109.6 . . ?
N3 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
N2 C4 C3 111.2(6) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?

_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_293K
_database_code_depnum_ccdc_archive 'CCDC 2083461'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 In, 1.5(C4 H16 N2)'
_chemical_formula_sum            'C6 H24 Br6 In N3'
_chemical_formula_weight         732.56
_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'
In In -0.7276 1.3100 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   22.548(10)
_cell_length_b                   8.033(4)
_cell_length_c                   11.737(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.770(15)
_cell_angle_gamma                90
_cell_volume                     2045.8(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.360
_shelx_estimated_absorpt_T_min   0.308
_exptl_absorpt_coefficient_mu    12.860
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2563
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1578 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.3437.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.507
_diffrn_reflns_theta_min         1.877
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1437
_reflns_number_total             2053
_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 V8.40A (?, 2016)'
_computing_data_collection       Bruker
_computing_data_reduction        'SAINT V8.40A (?, 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.300
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.00268(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+24.1980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C5
 1.5 with sigma of 0.002
 C5-N1
 1.45 with sigma of 0.002
 C6-C1
 1.5 with sigma of 0.002
 C2-C3
 1.5 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
N1 \\sim C5 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
N3 \\sim C6 \\sim C1: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
4. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) H3C(0.5) H3D(0.5) H3E(0.5) H2D(0.5)
 H2E(0.5) H2F(0.5) H1D(0.5) H1E(0.5) H1F(0.5) H3A(0.5) H3B(0.5) H6A(0.5)
 H6B(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) H5A(0.5) H5B(0.5) H4A(0.5)
 H4B(0.5) H4C(0.5)
5.a Riding coordinates:
 N2(H2A,H2B,H2C), N3(H3C,H3D,H3E), N1(H1D,H1E,H1F), C6(H6A,H6B), C1(H1A,H1B,
 H1C), C4(H4A,H4B,H4C)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C2(H2D,H2E,H2F)
;
_atom_sites_solution_hydrogens   mixed
_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
In1 In 0.66701(3) 0.5000 0.71257(5) 0.04777(17) Uani 1 2 d S T P . .
Br1 Br 0.75164(4) 0.73744(9) 0.77418(7) 0.0648(2) Uani 1 1 d . . . . .
Br3 Br 0.57950(3) 0.26414(9) 0.63563(7) 0.0672(2) Uani 1 1 d . . . . .
Br4 Br 0.68215(5) 0.5000 0.49101(8) 0.0805(4) Uani 1 2 d S T P . .
Br2 Br 0.64758(6) 0.5000 0.92372(9) 0.0842(4) Uani 1 2 d S T P . .
N2 N 0.6731(4) 1.0000 0.5321(6) 0.066(3) Uani 1 2 d S T P . .
H2A H 0.6729 0.8966 0.5592 0.079 Uiso 0.5 1 d R . . A -1
H2B H 0.6498 1.0647 0.5639 0.079 Uiso 0.5 1 d R . . A -1
H2C H 0.7116 1.0386 0.5514 0.079 Uiso 0.5 1 d R . . A -1
N3 N 0.5370(5) 0.5000 0.3425(9) 0.1109(10) Uani 1 2 d S TU P . .
H3C H 0.5188 0.4080 0.3584 0.133 Uiso 0.5 1 d R . . B -1
H3D H 0.5167 0.5888 0.3573 0.133 Uiso 0.5 1 d R . . B -1
H3E H 0.5757 0.5032 0.3877 0.133 Uiso 0.5 1 d R . . B -1
C2 C 0.58096(8) 1.0000 0.3600(10) 0.111(6) Uani 1 2 d DS T P . .
H2D H 0.5693 1.0439 0.2810 0.167 Uiso 0.5 1 calc GR . . C -1
H2E H 0.5636 1.0679 0.4101 0.167 Uiso 0.5 1 calc GR . . C -1
H2F H 0.5659 0.8882 0.3594 0.167 Uiso 0.5 1 calc GR . . C -1
N1 N 0.80601(8) 0.5000 1.0456(10) 0.1360(19) Uani 1 2 d DS TU P . .
H1D H 0.7929 0.5999 1.0167 0.163 Uiso 0.5 1 d R . . D -1
H1E H 0.7904 0.4764 1.1057 0.163 Uiso 0.5 1 d R . . D -1
H1F H 0.7937 0.4237 0.9892 0.163 Uiso 0.5 1 d R . . D -1
C3 C 0.64984(8) 1.0000 0.4062(10) 0.110(6) Uani 1 2 d DS T P . .
H3A H 0.6657 0.9026 0.3755 0.132 Uiso 0.5 1 calc R . . . .
H3B H 0.6657 1.0974 0.3755 0.132 Uiso 0.5 1 calc R . . . .
C6 C 0.53291(12) 0.5000 0.2211(3) 0.1133(9) Uani 1 2 d DS TU P . .
H6A H 0.5453 0.3892 0.2041 0.136 Uiso 0.5 1 d R . . . .
H6B H 0.4903 0.5189 0.1773 0.136 Uiso 0.5 1 d R . . . .
C1 C 0.56841(12) 0.6128(4) 0.1619(3) 0.1164(18) Uani 0.5 1 d D U . . .
H1A H 0.5550 0.6092 0.0770 0.175 Uiso 0.5 1 d R . . . .
H1B H 0.5633 0.7236 0.1884 0.175 Uiso 0.5 1 d R . . . .
H1C H 0.6111 0.5818 0.1884 0.175 Uiso 0.5 1 d R . . . .
C5 C 0.87269(6) 0.5000 1.08692(18) 0.1401(15) Uani 1 2 d DS TU P . .
H5A H 0.8845 0.4031 1.1373 0.168 Uiso 0.5 1 calc R . . . .
H5B H 0.8845 0.5969 1.1373 0.168 Uiso 0.5 1 calc R . . . .
C4 C 0.91192(10) 0.5000 1.00227(19) 0.1410(19) Uani 1 2 d DS TU P . .
H4A H 0.9525 0.4641 1.0448 0.211 Uiso 0.5 1 d R . . E -1
H4B H 0.9140 0.6104 0.9723 0.211 Uiso 0.5 1 d R . . E -1
H4C H 0.8955 0.4254 0.9375 0.211 Uiso 0.5 1 d R . . E -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
In1 Br1 2.6556(12) . ?
In1 Br1 2.6556(12) 6_565 ?
In1 Br3 2.7072(12) . ?
In1 Br3 2.7073(12) 6_565 ?
In1 Br4 2.7132(16) . ?
In1 Br2 2.6315(16) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8901 . ?
N2 H2C 0.8900 . ?
N2 C3 1.426(13) . ?
N3 H3C 0.8899 . ?
N3 H3D 0.8898 . ?
N3 H3E 0.8900 . ?
N3 C6 1.402(11) . ?
N3 C6 1.402(11) 6_565 ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C2 H2F 0.9600 . ?
C2 C3 1.4995(19) . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8901 . ?
N1 H1F 0.8899 . ?
N1 C5 1.4490(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C6 0.000000(3) 6_565 ?
C6 H6A 0.9699 . ?
C6 H6B 0.9700 . ?
C6 C1 1.4990(19) 6_565 ?
C6 C1 1.4990(19) . ?
C1 H1A 0.9602 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9595 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.4991(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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 In1 Br1 91.81(5) . 6_565 ?
Br1 In1 Br3 89.59(4) 6_565 . ?
Br1 In1 Br3 89.59(4) . 6_565 ?
Br1 In1 Br3 176.44(3) . . ?
Br1 In1 Br3 176.44(3) 6_565 6_565 ?
Br1 In1 Br4 89.58(3) . . ?
Br1 In1 Br4 89.58(3) 6_565 . ?
Br3 In1 Br3 88.82(5) . 6_565 ?
Br3 In1 Br4 87.16(3) . . ?
Br3 In1 Br4 87.16(3) 6_565 . ?
Br2 In1 Br1 91.99(3) . . ?
Br2 In1 Br1 91.99(3) . 6_565 ?
Br2 In1 Br3 91.22(4) . 6_565 ?
Br2 In1 Br3 91.22(4) . . ?
Br2 In1 Br4 177.74(5) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C3 N2 H2A 109.6 . . ?
C3 N2 H2B 110.0 . . ?
C3 N2 H2C 108.9 . . ?
H3C N3 H3D 109.5 . . ?
H3C N3 H3E 109.5 . . ?
H3D N3 H3E 109.5 . . ?
C6 N3 H3C 107.8 . . ?
C6 N3 H3C 107.8 6_565 . ?
C6 N3 H3D 107.6 6_565 . ?
C6 N3 H3D 107.6 . . ?
C6 N3 H3E 112.9 . . ?
C6 N3 H3E 112.9 6_565 . ?
C6 N3 C6 0.0 6_565 . ?
H2D C2 H2E 109.5 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?
C3 C2 H2D 109.5 . . ?
C3 C2 H2E 109.5 . . ?
C3 C2 H2F 109.5 . . ?
H1D N1 H1E 109.5 . . ?
H1D N1 H1F 109.5 . . ?
H1E N1 H1F 109.5 . . ?
C5 N1 H1D 109.5 . . ?
C5 N1 H1E 109.4 . . ?
C5 N1 H1F 109.5 . . ?
N2 C3 C2 115.3(8) . . ?
N2 C3 H3A 108.4 . . ?
N2 C3 H3B 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
N3 C6 H6A 105.4 . . ?
N3 C6 H6B 108.7 . . ?
N3 C6 C1 125.1(4) . 6_565 ?
N3 C6 C1 125.1(4) . . ?
C6 C6 N3 0(10) 6_565 . ?
C6 C6 H6A 0.0 6_565 . ?
C6 C6 H6B 0.0 6_565 . ?
C6 C6 C1 0(10) 6_565 . ?
C6 C6 C1 0(10) 6_565 6_565 ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6A 29.5 6_565 . ?
C1 C6 H6A 103.9 . . ?
C1 C6 H6B 103.7 . . ?
C1 C6 H6B 115.2 6_565 . ?
C1 C6 C1 74.4(3) . 6_565 ?
C6 C1 H1A 113.9 . . ?
C6 C1 H1B 106.5 . . ?
C6 C1 H1C 107.9 . . ?
H1A C1 H1B 109.4 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C5 H5A 106.9 . . ?
N1 C5 H5B 106.9 . . ?
N1 C5 C4 121.6(5) . . ?
H5A C5 H5B 106.7 . . ?
C4 C5 H5A 106.9 . . ?
C4 C5 H5B 106.9 . . ?
C5 C4 H4A 107.8 . . ?
C5 C4 H4B 109.8 . . ?
C5 C4 H4C 110.8 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.4 . . ?
H4B C4 H4C 109.5 . . ?

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
C6 N3 C6 C1 0(100) 6_565 . . . ?
C6 N3 C6 C1 0(100) 6_565 . . 6_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
