# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_c
_database_code_depnum_ccdc_archive 'CCDC 2076595'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-04-10 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 In, C12 H28 N'
_chemical_formula_sum            'C12 H28 Cl4 In N'
_chemical_formula_weight         442.97
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   14.299(4)
_cell_length_b                   16.580(5)
_cell_length_c                   17.771(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4213(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    788
_cell_measurement_temperature    380
_cell_measurement_theta_max      14.466
_cell_measurement_theta_min      2.203
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1711 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.7572.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_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  0.1194
_diffrn_reflns_av_unetI/netI     0.1209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_temperature      380
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source_current           0.6
_diffrn_source_power             0.03
_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                1163
_reflns_number_total             3859
_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       ?
_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         0.440
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.2182
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      0.947
_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)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 In1-Cl4B \\sim In1-Cl4A
 with sigma of 0.02
 In1-Cl1B \\sim In1-Cl1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl4A \\sim Cl4B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Cl1B \\sim Cl1A: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Cl3A \\sim Cl3B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
4. Rigid body (RIGU) restrains
 C12, N1, C10, C7, C4, C1, C11, C8, C5, C2, C9, C6, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl4A, Cl4B, In1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 In1, Cl2, Cl3B, Cl1B, Cl4B, Cl4A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(Cl4B)=1-FVAR(1)
 Sof(Cl4A)=FVAR(1)
 Sof(Cl3B)=1-FVAR(2)
 Sof(Cl3A)=FVAR(2)
 Sof(Cl1B)=1-FVAR(3)
 Sof(Cl1A)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B), C4(H4A,H4B), C1(H1A,H1B), C11(H11A,H11B), C2(H2A,
 H2B), C8(H8A,H8B), C5(H5A,H5B)
6.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C12(H12A,H12B,H12C)
;
_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 0.27906(7) 0.59660(5) 0.65786(4) 0.1143(4) Uani 1 1 d D . . . .
Cl2 Cl 0.2165(3) 0.67013(18) 0.75721(18) 0.1478(12) Uani 1 1 d . . . . .
Cl3B Cl 0.435(7) 0.564(5) 0.645(10) 0.179(6) Uani 0.10(6) 1 d . U P A 2
Cl1B Cl 0.178(5) 0.537(6) 0.574(5) 0.209(5) Uani 0.050(7) 1 d D U P A 2
Cl4B Cl 0.2577(18) 0.6618(16) 0.5420(8) 0.185(5) Uani 0.56(4) 1 d D U P A 2
N1 N 0.4677(6) 0.6935(4) 0.3604(4) 0.097(2) Uani 1 1 d . . . . .
C10 C 0.5586(8) 0.6678(5) 0.4003(5) 0.116(3) Uani 1 1 d . . . . .
H10A H 0.578465 0.617045 0.378232 0.139 Uiso 1 1 calc R U . . .
H10B H 0.606174 0.707395 0.388165 0.139 Uiso 1 1 calc R U . . .
C7 C 0.4301(9) 0.7689(6) 0.3929(6) 0.129(3) Uani 1 1 d . . . . .
H7A H 0.376791 0.783613 0.362004 0.154 Uiso 1 1 calc R U . . .
H7B H 0.405171 0.754567 0.441871 0.154 Uiso 1 1 calc R U . . .
C4 C 0.4852(9) 0.7070(6) 0.2789(5) 0.129(3) Uani 1 1 d . . . . .
H4A H 0.426782 0.726915 0.258314 0.154 Uiso 1 1 calc R U . . .
H4B H 0.529088 0.751566 0.276096 0.154 Uiso 1 1 calc R U . . .
C1 C 0.3983(10) 0.6252(7) 0.3714(6) 0.139(3) Uani 1 1 d . . . . .
H1A H 0.430331 0.575725 0.357776 0.167 Uiso 1 1 calc R U . . .
H1B H 0.385579 0.621994 0.424913 0.167 Uiso 1 1 calc R U . . .
C11 C 0.5583(10) 0.6578(8) 0.4798(6) 0.166(5) Uani 1 1 d . . . . .
H11A H 0.507948 0.621128 0.492864 0.199 Uiso 1 1 calc R U . . .
H11B H 0.543997 0.709502 0.502603 0.199 Uiso 1 1 calc R U . . .
C2 C 0.3144(13) 0.6240(10) 0.3359(7) 0.180(6) Uani 1 1 d . . . . .
H2A H 0.324636 0.625728 0.281955 0.216 Uiso 1 1 calc R U . . .
H2B H 0.279432 0.671865 0.349787 0.216 Uiso 1 1 calc R U . . .
C8 C 0.4810(10) 0.8391(6) 0.4034(7) 0.161(5) Uani 1 1 d . . . . .
H8A H 0.506611 0.854068 0.354802 0.193 Uiso 1 1 calc R U . . .
H8B H 0.533689 0.825597 0.435403 0.193 Uiso 1 1 calc R U . . .
C9 C 0.4381(10) 0.9109(6) 0.4348(7) 0.166(5) Uani 1 1 d . . . . .
H9A H 0.384176 0.925138 0.405462 0.249 Uiso 1 1 calc R U . . .
H9B H 0.482203 0.954478 0.433947 0.249 Uiso 1 1 calc R U . . .
H9C H 0.419383 0.900438 0.485763 0.249 Uiso 1 1 calc R U . . .
C6 C 0.5198(11) 0.6737(8) 0.1469(5) 0.175(6) Uani 1 1 d . . . . .
H6A H 0.497527 0.629165 0.117433 0.262 Uiso 1 1 calc R U . . .
H6B H 0.582999 0.686019 0.132874 0.262 Uiso 1 1 calc R U . . .
H6C H 0.480878 0.719967 0.138057 0.262 Uiso 1 1 calc R U . . .
C3 C 0.2568(10) 0.5503(8) 0.3547(7) 0.173(6) Uani 1 1 d . . . . .
H3A H 0.200952 0.550085 0.324626 0.260 Uiso 1 1 calc R U . . .
H3B H 0.240175 0.551391 0.406993 0.260 Uiso 1 1 calc R U . . .
H3C H 0.292547 0.502586 0.344282 0.260 Uiso 1 1 calc R U . . .
C5 C 0.5164(11) 0.6517(8) 0.2296(5) 0.184(6) Uani 1 1 d . . . . .
H5A H 0.477332 0.604165 0.234653 0.221 Uiso 1 1 calc R U . . .
H5B H 0.579080 0.636380 0.244808 0.221 Uiso 1 1 calc R U . . .
C12 C 0.6455(11) 0.6270(8) 0.5140(6) 0.194(6) Uani 1 1 d . . . . .
H12A H 0.658934 0.574371 0.494244 0.291 Uiso 1 1 calc R U . . .
H12B H 0.638032 0.623748 0.567571 0.291 Uiso 1 1 calc R U . . .
H12C H 0.696095 0.662907 0.502269 0.291 Uiso 1 1 calc R U . . .
Cl4A Cl 0.285(2) 0.6952(18) 0.5630(15) 0.190(6) Uani 0.44(4) 1 d D U P A 1
Cl3A Cl 0.4345(6) 0.5675(4) 0.6852(17) 0.172(5) Uani 0.90(6) 1 d . U P A 1
Cl1A Cl 0.1956(4) 0.4787(3) 0.6389(3) 0.214(3) Uani 0.950(7) 1 d D U P A 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 Cl2 2.324(3) . ?
In1 Cl3B 2.31(8) . ?
In1 Cl1B 2.29(2) . ?
In1 Cl4B 2.346(9) . ?
In1 Cl4A 2.350(11) . ?
In1 Cl3A 2.326(7) . ?
In1 Cl1A 2.315(4) . ?
Cl1B Cl4B 2.43(10) . ?
N1 C10 1.541(12) . ?
N1 C7 1.479(10) . ?
N1 C4 1.487(11) . ?
N1 C1 1.519(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.424(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.386(13) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.344(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.356(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.477(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.450(12) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C5 1.515(12) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
Cl2 In1 Cl4B 112.0(6) . . ?
Cl2 In1 Cl4A 101.2(8) . . ?
Cl2 In1 Cl3A 108.5(7) . . ?
Cl3B In1 Cl2 125(4) . . ?
Cl3B In1 Cl4B 99(4) . . ?
Cl1B In1 Cl2 118(2) . . ?
Cl1B In1 Cl3B 116(5) . . ?
Cl1B In1 Cl4B 63(3) . . ?
Cl3A In1 Cl4A 105.0(9) . . ?
Cl1A In1 Cl2 110.81(15) . . ?
Cl1A In1 Cl4A 120.2(10) . . ?
Cl1A In1 Cl3A 110.4(3) . . ?
In1 Cl1B Cl4B 59.5(16) . . ?
In1 Cl4B Cl1B 57.4(15) . . ?
C7 N1 C10 111.2(7) . . ?
C7 N1 C4 108.4(7) . . ?
C7 N1 C1 110.0(9) . . ?
C4 N1 C10 110.4(9) . . ?
C4 N1 C1 110.4(8) . . ?
C1 N1 C10 106.6(8) . . ?
N1 C10 H10A 107.5 . . ?
N1 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C11 C10 N1 119.1(10) . . ?
C11 C10 H10A 107.5 . . ?
C11 C10 H10B 107.5 . . ?
N1 C7 H7A 106.1 . . ?
N1 C7 H7B 106.1 . . ?
H7A C7 H7B 106.3 . . ?
C8 C7 N1 124.8(12) . . ?
C8 C7 H7A 106.1 . . ?
C8 C7 H7B 106.1 . . ?
N1 C4 H4A 105.8 . . ?
N1 C4 H4B 105.8 . . ?
H4A C4 H4B 106.2 . . ?
C5 C4 N1 126.0(10) . . ?
C5 C4 H4A 105.8 . . ?
C5 C4 H4B 105.8 . . ?
N1 C1 H1A 106.8 . . ?
N1 C1 H1B 106.8 . . ?
H1A C1 H1B 106.7 . . ?
C2 C1 N1 122.0(12) . . ?
C2 C1 H1A 106.8 . . ?
C2 C1 H1B 106.8 . . ?
C10 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C10 C11 C12 116.4(12) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 113.1(14) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C7 C8 H8A 107.0 . . ?
C7 C8 H8B 107.0 . . ?
C7 C8 C9 121.2(13) . . ?
H8A C8 H8B 106.8 . . ?
C9 C8 H8A 107.0 . . ?
C9 C8 H8B 107.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C5 C6 118.5(11) . . ?
C4 C5 H5A 107.7 . . ?
C4 C5 H5B 107.7 . . ?
C6 C5 H5A 107.7 . . ?
C6 C5 H5B 107.7 . . ?
H5A C5 H5B 107.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C10 C11 C12 175.5(11) . . . . ?
N1 C7 C8 C9 179.1(10) . . . . ?
N1 C4 C5 C6 173.2(12) . . . . ?
N1 C1 C2 C3 179.7(11) . . . . ?
C10 N1 C7 C8 51.3(13) . . . . ?
C10 N1 C4 C5 60.5(16) . . . . ?
C10 N1 C1 C2 -172.2(14) . . . . ?
C7 N1 C10 C11 55.0(13) . . . . ?
C7 N1 C4 C5 -177.5(14) . . . . ?
C7 N1 C1 C2 67.2(16) . . . . ?
C4 N1 C10 C11 175.3(9) . . . . ?
C4 N1 C7 C8 -70.2(13) . . . . ?
C4 N1 C1 C2 -52.3(17) . . . . ?
C1 N1 C10 C11 -64.9(12) . . . . ?
C1 N1 C7 C8 169.1(11) . . . . ?
C1 N1 C4 C5 -57.0(17) . . . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 2083457'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_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         'Br5 H2 In O, 2(C8 H12 N)'
_chemical_formula_sum            'C16 H26 Br5 In N2 O'
_chemical_formula_weight         776.76
_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'
O O 0.0106 0.0060 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.264(19)
_cell_length_b                   8.874(12)
_cell_length_c                   19.71(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.673(18)
_cell_angle_gamma                90
_cell_volume                     2349(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    110
_cell_measurement_theta_max      26.801
_cell_measurement_theta_min      2.544
_shelx_estimated_absorpt_T_max   0.450
_shelx_estimated_absorpt_T_min   0.395
_exptl_absorpt_coefficient_mu    9.518
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.6286.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_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  0.0698
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19349
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.150
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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_source_current           0.6
_diffrn_source_power             0.03
_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                3956
_reflns_number_total             5359
_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       ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.005
_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)+(0.0227P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0710
_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,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1F,H1G)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 N1(H1B,H1A,H1C), N2(H2C,H2D,H2E)
;
_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
In1 In 0.05840(2) 1.22993(3) 0.12263(2) 0.01218(8) Uani 1 1 d . . . . .
Br1 Br 0.21588(4) 1.39835(5) 0.12892(2) 0.01590(11) Uani 1 1 d . . . . .
Br2 Br 0.16861(4) 0.98000(5) 0.13463(2) 0.01712(11) Uani 1 1 d . . . . .
Br3 Br 0.09668(4) 1.24694(5) 0.26118(2) 0.01704(11) Uani 1 1 d . . . . .
Br4 Br -0.10153(4) 1.06224(5) 0.09302(2) 0.01636(11) Uani 1 1 d . . . . .
Br5 Br -0.05395(4) 1.48098(5) 0.09322(2) 0.01591(11) Uani 1 1 d . . . . .
O1 O 0.0290(2) 1.2223(3) 0.00174(16) 0.0180(7) Uani 1 1 d . . . . .
H1F H 0.034187 1.141764 -0.025245 0.027 Uiso 1 1 d R U . . .
H1G H 0.009581 1.298992 -0.030446 0.027 Uiso 1 1 d R U . . .
N1 N 0.1446(3) 0.6479(4) 0.2358(2) 0.0192(9) Uani 1 1 d . . . . .
H1B H 0.190767 0.581434 0.259536 0.023 Uiso 1 1 calc R U . . .
H1A H 0.173410 0.736296 0.234436 0.023 Uiso 1 1 calc R U . . .
H1C H 0.114141 0.615259 0.191080 0.023 Uiso 1 1 calc R U . . .
C1 C 0.0698(4) 0.6659(5) 0.2736(2) 0.0151(10) Uani 1 1 d . . . . .
H1D H 0.031829 0.573547 0.269310 0.018 Uiso 1 1 calc R U . . .
H1E H 0.103926 0.685380 0.324358 0.018 Uiso 1 1 calc R U . . .
C2 C 0.0009(4) 0.7936(5) 0.2411(3) 0.0180(10) Uani 1 1 d . . . . .
H2A H -0.030178 0.776038 0.189768 0.022 Uiso 1 1 calc R U . . .
H2B H 0.039019 0.886196 0.247245 0.022 Uiso 1 1 calc R U . . .
C3 C -0.0793(4) 0.8116(5) 0.2751(2) 0.0147(10) Uani 1 1 d . . . . .
C4 C -0.0869(4) 0.9424(5) 0.3113(2) 0.0196(11) Uani 1 1 d . . . . .
H4 H -0.041511 1.020145 0.315661 0.023 Uiso 1 1 calc R U . . .
C5 C -0.1622(4) 0.9587(6) 0.3415(3) 0.0267(12) Uani 1 1 d . . . . .
H5 H -0.167660 1.047896 0.364703 0.032 Uiso 1 1 calc R U . . .
C6 C -0.2283(4) 0.8429(6) 0.3369(3) 0.0261(12) Uani 1 1 d . . . . .
H6 H -0.277312 0.853504 0.357988 0.031 Uiso 1 1 calc R U . . .
C7 C -0.2226(4) 0.7119(6) 0.3015(3) 0.0272(12) Uani 1 1 d . . . . .
H7 H -0.268162 0.634615 0.297572 0.033 Uiso 1 1 calc R U . . .
C8 C -0.1467(4) 0.6963(6) 0.2712(3) 0.0207(11) Uani 1 1 d . . . . .
H8 H -0.141650 0.606886 0.248122 0.025 Uiso 1 1 calc R U . . .
N2 N -0.2569(3) 0.7873(4) 0.5403(2) 0.0183(9) Uani 1 1 d . . . . .
H2C H -0.291579 0.737853 0.500443 0.022 Uiso 1 1 calc R U . . .
H2D H -0.284771 0.876778 0.540875 0.022 Uiso 1 1 calc R U . . .
H2E H -0.256544 0.734431 0.578730 0.022 Uiso 1 1 calc R U . . .
C9 C -0.1519(4) 0.8089(5) 0.5416(2) 0.0161(10) Uani 1 1 d . . . . .
H9A H -0.113958 0.861506 0.585350 0.019 Uiso 1 1 calc R U . . .
H9B H -0.152189 0.870626 0.500894 0.019 Uiso 1 1 calc R U . . .
C10 C -0.1026(4) 0.6591(5) 0.5383(3) 0.0217(11) Uani 1 1 d . . . . .
H10A H -0.103573 0.596674 0.578421 0.026 Uiso 1 1 calc R U . . .
H10B H -0.139962 0.607368 0.494048 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0037(4) 0.6800(5) 0.5410(2) 0.0159(10) Uani 1 1 d . . . . .
C12 C 0.0829(4) 0.6401(5) 0.6007(3) 0.0237(12) Uani 1 1 d . . . . .
H12 H 0.070997 0.600165 0.640655 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1806(4) 0.6583(6) 0.6023(3) 0.0314(13) Uani 1 1 d . . . . .
H13 H 0.233346 0.628019 0.642535 0.038 Uiso 1 1 calc R U . . .
C14 C 0.1990(4) 0.7218(6) 0.5439(3) 0.0293(13) Uani 1 1 d . . . . .
H14 H 0.264077 0.737519 0.545409 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1209(4) 0.7613(6) 0.4839(3) 0.0285(13) Uani 1 1 d . . . . .
H15 H 0.132953 0.802641 0.444212 0.034 Uiso 1 1 calc R U . . .
C16 C 0.0236(4) 0.7395(5) 0.4823(3) 0.0227(11) Uani 1 1 d . . . . .
H16 H -0.029051 0.765299 0.441061 0.027 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 2.666(3) . ?
In1 Br2 2.683(3) . ?
In1 Br3 2.603(4) . ?
In1 Br4 2.620(3) . ?
In1 Br5 2.691(3) . ?
In1 O1 2.277(4) . ?
O1 H1F 0.9082 . ?
O1 H1G 0.9082 . ?
N1 H1B 0.8900 . ?
N1 H1A 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.502(6) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.495(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.516(7) . ?
C3 C4 1.387(6) . ?
C3 C8 1.389(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.408(7) . ?
C8 H8 0.9300 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N2 C9 1.501(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.516(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(7) . ?
C11 C12 1.376(7) . ?
C11 C16 1.385(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(8) . ?
C16 H16 0.9300 . ?

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 Br2 89.99(10) . . ?
Br1 In1 Br5 88.70(10) . . ?
Br2 In1 Br5 172.87(2) . . ?
Br3 In1 Br1 92.45(3) . . ?
Br3 In1 Br2 92.62(2) . . ?
Br3 In1 Br4 97.24(2) . . ?
Br3 In1 Br5 94.44(3) . . ?
Br4 In1 Br1 170.31(3) . . ?
Br4 In1 Br2 89.46(10) . . ?
Br4 In1 Br5 90.66(10) . . ?
O1 In1 Br1 85.46(8) . . ?
O1 In1 Br2 87.91(8) . . ?
O1 In1 Br3 177.84(8) . . ?
O1 In1 Br4 84.85(8) . . ?
O1 In1 Br5 85.01(8) . . ?
In1 O1 H1F 127.9 . . ?
In1 O1 H1G 127.9 . . ?
H1F O1 H1G 104.3 . . ?
H1B N1 H1A 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.7 . . ?
N1 C1 H1E 109.7 . . ?
H1D C1 H1E 108.2 . . ?
C2 C1 N1 110.0(4) . . ?
C2 C1 H1D 109.7 . . ?
C2 C1 H1E 109.7 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 112.0(4) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 C8 118.1(5) . . ?
C8 C3 C2 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(5) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.0(5) . . ?
C8 C7 H7 120.5 . . ?
C3 C8 C7 121.5(5) . . ?
C3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
H2C N2 H2D 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C9 N2 H2C 109.5 . . ?
C9 N2 H2D 109.5 . . ?
C9 N2 H2E 109.5 . . ?
N2 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
N2 C9 C10 111.2(4) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.4(4) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C12 C11 C10 121.6(5) . . ?
C12 C11 C16 118.2(5) . . ?
C16 C11 C10 120.2(4) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.1(5) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 121.2(5) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?

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
N1 C1 C2 C3 177.3(4) . . . . ?
C1 C2 C3 C4 118.1(5) . . . . ?
C1 C2 C3 C8 -61.3(6) . . . . ?
C2 C3 C4 C5 179.0(4) . . . . ?
C2 C3 C8 C7 -179.0(5) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C3 C8 C7 1.6(7) . . . . ?
C4 C5 C6 C7 -1.4(8) . . . . ?
C5 C6 C7 C8 1.3(8) . . . . ?
C6 C7 C8 C3 -1.4(8) . . . . ?
C8 C3 C4 C5 -1.6(7) . . . . ?
N2 C9 C10 C11 -178.9(4) . . . . ?
C9 C10 C11 C12 108.9(5) . . . . ?
C9 C10 C11 C16 -71.6(6) . . . . ?
C10 C11 C12 C13 179.3(4) . . . . ?
C10 C11 C16 C15 179.3(5) . . . . ?
C11 C12 C13 C14 1.9(8) . . . . ?
C12 C11 C16 C15 -1.2(7) . . . . ?
C12 C13 C14 C15 -2.3(8) . . . . ?
C13 C14 C15 C16 0.9(8) . . . . ?
C14 C15 C16 C11 0.9(8) . . . . ?
C16 C11 C12 C13 -0.2(7) . . . . ?

_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_ee
_database_code_depnum_ccdc_archive 'CCDC 2083459'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-15
_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         'Br5 H2 In O, C16 H24 N2'
_chemical_formula_sum            'C16 H24 Br5 In N2 O'
_chemical_formula_weight         774.74
_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'
O O 0.0106 0.0060 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.912(8)
_cell_length_b                   8.556(7)
_cell_length_c                   14.164(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.910(14)
_cell_angle_gamma                90
_cell_volume                     1235.3(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.051
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.0825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1603 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.1106.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1535
_diffrn_reflns_av_unetI/netI     0.1707
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5950
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1307
_reflns_number_total             2327
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         3.025
_refine_diff_density_min         -2.158
_refine_diff_density_rms         0.272
_refine_ls_extinction_coef       0.0117(6)
_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   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     130
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.0921
_refine_ls_restrained_S_all      0.984
_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)+(0.1423P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2229
_refine_ls_wR_factor_ref         0.2602
_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,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C6-C5
 1.38 with sigma of 0.02
3. Rigid bond restraints
 C4, C5, C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C4 \\sim C2: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C16) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: H1WA(0.5) H1WB(0.5) H2A(0.5) H2C(0.5) H2B(0.5) H1A(0.5) H1B(0.5)
 H1C(0.5) C11(0.5) C16(0.5) H16(0.5) C15(0.5) H15(0.5) C14(0.5) H14(0.5)
 C13(0.5) H13(0.5) C12(0.5) H12(0.5) C8(0.5) H8(0.5) C3(0.5) C7(0.5) H7(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C2(0.5) H2D(0.5)
 H2E(0.5) H4(0.5) H6(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5)
6.a Riding coordinates:
 O1W(H1WA,H1WB)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C2(H2D,H2E), C1A(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C14(H14), C13(H13), C12(H12), C8(H8), C5(H5), C7(H7),
 C4(H4), C6(H6)
6.d Fitted hexagon refined as free rotating group:
 C11(C16,C15,C14,C13,C12)
6.e Idealised Me refined as rotating group:
 N2(H2A,H2C,H2B), N1(H1A,H1B,H1C)
;
_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
In1 In 0.25933(6) 0.2500 0.43961(5) 0.0341(2) Uani 1 2 d S T P . .
Br2 Br 0.31595(6) 0.02539(9) 0.33228(5) 0.0437(2) Uani 1 1 d . . . . .
Br3 Br 0.24251(7) 0.03473(11) 0.57255(6) 0.0589(3) Uani 1 1 d . . . . .
Br1 Br 0.00797(9) 0.2500 0.34117(8) 0.0541(4) Uani 1 2 d S T P . .
O1W O 0.4833(6) 0.2500 0.5224(5) 0.054(3) Uani 1 2 d S T P . .
H1WA H 0.5248 0.1994 0.4812 0.081 Uiso 0.5 1 d R . . A -1
H1WB H 0.5042 0.1948 0.5852 0.081 Uiso 0.5 1 d R . . A -1
N2 N 0.0422(9) -0.2500 0.4117(6) 0.068(3) Uani 1 2 d S TU P . .
H2A H -0.0349 -0.2446 0.4197 0.082 Uiso 0.5 1 calc GR . . B -1
H2C H 0.0965 -0.1793 0.4511 0.082 Uiso 0.5 1 calc GR . . B -1
H2B H 0.0761 -0.3451 0.4286 0.082 Uiso 0.5 1 calc GR . . B -1
N1 N 0.5534(8) 0.2500 0.2994(6) 0.057(3) Uani 1 2 d S TU P . .
H1A H 0.4851 0.3071 0.2991 0.068 Uiso 0.5 1 calc GR . . C -1
H1B H 0.6274 0.2972 0.3370 0.068 Uiso 0.5 1 calc GR . . C -1
H1C H 0.5493 0.1560 0.3250 0.068 Uiso 0.5 1 calc GR . . C -1
C11 C -0.1066(6) -0.2162(9) 0.1270(5) 0.066(3) Uani 0.5 1 d . U . D -1
C16 C -0.1780(9) -0.3380(11) 0.0676(6) 0.054(3) Uani 0.5 1 d G U . D -1
H16 H -0.2151 -0.4141 0.0960 0.065 Uiso 0.5 1 calc R . . D -1
C15 C -0.1939(11) -0.3461(14) -0.0341(6) 0.059(3) Uani 0.5 1 d G U . D -1
H15 H -0.2416 -0.4276 -0.0738 0.071 Uiso 0.5 1 calc R . . D -1
C14 C -0.1384(11) -0.2324(17) -0.0764(5) 0.057(3) Uani 0.5 1 d G U . D -1
H14 H -0.1490 -0.2377 -0.1445 0.069 Uiso 0.5 1 calc R . . D -1
C13 C -0.0670(11) -0.1106(15) -0.0170(7) 0.080(3) Uani 0.5 1 d G U . D -1
H13 H -0.0299 -0.0345 -0.0454 0.097 Uiso 0.5 1 calc R . . D -1
C12 C -0.0511(9) -0.1025(11) 0.0847(6) 0.078(3) Uani 0.5 1 d G U . D -1
H12 H -0.0034 -0.0210 0.1244 0.093 Uiso 0.5 1 calc R . . D -1
C8 C 0.4965(15) 0.343(2) -0.0414(12) 0.063(3) Uani 0.5 1 d . U . E -1
H8 H 0.4268 0.3977 -0.0345 0.076 Uiso 0.5 1 calc R . . E -1
C3 C 0.5957(13) 0.3105(15) 0.0437(10) 0.048(3) Uani 0.5 1 d . U . E -1
C5 C 0.6943(10) 0.2500 -0.0728(8) 0.1017(17) Uani 1 2 d DS TU P E .
H5 H 0.7716 0.2500 -0.0864 0.122 Uiso 1 2 calc RS T P . .
C7 C 0.4855(16) 0.306(2) -0.1324(12) 0.086(3) Uani 0.5 1 d . U . E -1
H7 H 0.4051 0.3220 -0.1841 0.103 Uiso 0.5 1 calc R . . E -1
C10 C -0.0873(17) -0.193(2) 0.2445(12) 0.091(4) Uani 0.5 1 d . U . D -1
H10A H -0.1108 -0.0863 0.2537 0.109 Uiso 0.5 1 calc R . . D -1
H10B H -0.1487 -0.2612 0.2598 0.109 Uiso 0.5 1 calc R . . D -1
C9 C 0.0245(10) -0.219(2) 0.3072(8) 0.051(3) Uani 0.5 1 d . U . D -1
H9A H 0.0789 -0.1299 0.3064 0.061 Uiso 0.5 1 calc R . . D -1
H9B H 0.0597 -0.3081 0.2827 0.061 Uiso 0.5 1 calc R . . D -1
C2 C 0.6159(18) 0.343(3) 0.1557(13) 0.097(4) Uani 0.5 1 d . U . E -1
H2D H 0.7090 0.3409 0.1954 0.117 Uiso 0.5 1 calc R . . E -1
H2E H 0.5834 0.4468 0.1614 0.117 Uiso 0.5 1 calc R . . E -1
C4 C 0.7064(13) 0.2500 0.0271(10) 0.090(2) Uani 1 2 d S TU P . .
H4 H 0.7805 0.2136 0.0789 0.108 Uiso 0.5 1 calc R . . E .
C6 C 0.5793(10) 0.2500 -0.1543(8) 0.0913(17) Uani 1 2 d DS TU P . .
H6 H 0.5710 0.2132 -0.2181 0.110 Uiso 0.5 1 calc R . . E .
C1A C 0.5510(14) 0.233(5) 0.1949(10) 0.0958(4) Uani 0.5 1 d . U . E -1
H1AA H 0.5872 0.1309 0.1901 0.115 Uiso 0.5 1 calc R . . E -1
H1AB H 0.4597 0.2312 0.1505 0.115 Uiso 0.5 1 calc 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 Br2 2.6563(17) 4_565 ?
In1 Br2 2.6563(17) . ?
In1 Br3 2.6868(18) . ?
In1 Br3 2.6868(18) 4_565 ?
In1 Br1 2.596(2) . ?
In1 O1W 2.302(6) . ?
O1W H1WA 0.9595 . ?
O1W H1WB 0.9606 . ?
N2 H2A 0.8900 . ?
N2 H2C 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C9 1.446(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1A 1.478(17) . ?
C11 C16 1.3900 . ?
C11 C12 1.3900 . ?
C11 C10 1.613(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C8 C3 1.330(18) . ?
C8 C7 1.29(2) . ?
C3 C2 1.55(2) . ?
C3 C4 1.41(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(18) . ?
C5 C6 1.369(11) . ?
C7 H7 0.9300 . ?
C7 C6 1.27(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.246(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C2 C1A 1.41(4) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?

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 In1 Br2 92.68(7) 4_565 . ?
Br2 In1 Br3 170.08(3) 4_565 . ?
Br2 In1 Br3 89.61(7) . . ?
Br2 In1 Br3 170.09(3) . 4_565 ?
Br2 In1 Br3 89.61(7) 4_565 4_565 ?
Br3 In1 Br3 86.56(8) 4_565 . ?
Br1 In1 Br2 96.29(4) . 4_565 ?
Br1 In1 Br2 96.29(4) . . ?
Br1 In1 Br3 93.04(4) . 4_565 ?
Br1 In1 Br3 93.04(4) . . ?
O1W In1 Br2 82.53(14) . 4_565 ?
O1W In1 Br2 82.53(14) . . ?
O1W In1 Br3 88.21(15) . . ?
O1W In1 Br3 88.21(15) . 4_565 ?
O1W In1 Br1 178.3(2) . . ?
In1 O1W H1WA 109.7 . . ?
In1 O1W H1WB 109.3 . . ?
H1WA O1W H1WB 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2C N2 H2B 109.5 . . ?
C9 N2 H2A 109.5 . . ?
C9 N2 H2C 109.5 . . ?
C9 N2 H2B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1A N1 H1A 109.5 . . ?
C1A N1 H1B 109.5 . . ?
C1A N1 H1C 109.5 . . ?
C16 C11 C12 120.0 . . ?
C16 C11 C10 123.7(8) . . ?
C12 C11 C10 116.3(8) . . ?
C11 C16 H16 120.0 . . ?
C11 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
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 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C3 C8 H8 116.1 . . ?
C7 C8 H8 116.1 . . ?
C7 C8 C3 127.8(17) . . ?
C8 C3 C2 131.7(16) . . ?
C8 C3 C4 113.1(14) . . ?
C4 C3 C2 114.8(12) . . ?
C4 C5 H5 116.9 . . ?
C6 C5 H5 116.9 . . ?
C6 C5 C4 126.2(12) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 C8 122.8(14) . . ?
C6 C7 H7 118.6 . . ?
C11 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C9 C10 C11 116.6(15) . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
N2 C9 H9A 107.3 . . ?
N2 C9 H9B 107.3 . . ?
C10 C9 N2 120.1(14) . . ?
C10 C9 H9A 107.3 . . ?
C10 C9 H9B 107.3 . . ?
H9A C9 H9B 106.9 . . ?
C3 C2 H2D 109.2 . . ?
C3 C2 H2E 109.2 . . ?
H2D C2 H2E 107.9 . . ?
C1A C2 C3 112.1(16) . . ?
C1A C2 H2D 109.2 . . ?
C1A C2 H2E 109.2 . . ?
C3 C4 H4 123.2 . . ?
C5 C4 C3 113.5(10) . . ?
C5 C4 H4 123.2 . . ?
C5 C6 H6 124.1 . . ?
C7 C6 C5 111.8(12) . . ?
C7 C6 H6 124.1 . . ?
N1 C1A H1AA 107.4 . . ?
N1 C1A H1AB 107.4 . . ?
C2 C1A N1 120(2) . . ?
C2 C1A H1AA 107.4 . . ?
C2 C1A H1AB 107.4 . . ?
H1AA C1A H1AB 106.9 . . ?

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
C11 C16 C15 C14 0.0 . . . . ?
C11 C10 C9 N2 -160.4(12) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C16 C11 C10 C9 109.1(17) . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C12 C11 C10 C9 -73.3(19) . . . . ?
C8 C3 C2 C1A 80(2) . . . . ?
C8 C3 C4 C5 5.8(15) . . . . ?
C8 C7 C6 C5 -7(2) . . . . ?
C3 C8 C7 C6 -10(3) . . . . ?
C3 C2 C1A N1 -176.8(16) . . . . ?
C7 C8 C3 C2 -177.4(19) . . . . ?
C7 C8 C3 C4 10(3) . . . . ?
C10 C11 C16 C15 177.6(9) . . . . ?
C10 C11 C12 C13 -177.8(8) . . . . ?
C2 C3 C4 C5 -168.3(11) . . . . ?
C4 C3 C2 C1A -106.9(18) . . . . ?
C4 C5 C6 C7 24.1(10) . . . . ?
C6 C5 C4 C3 -23.6(7) . . . . ?

_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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2083456'
loop_
_audit_author_name
_audit_author_address
'Guancheng Xu'
;XinJiang University
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_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         'Cl4 In, C12 H28 N'
_chemical_formula_sum            'C12 H28 Cl4 In N'
_chemical_formula_weight         442.97
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   13.6589(10)
_cell_length_b                   16.4433(12)
_cell_length_c                   17.4222(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3913.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.468
_cell_measurement_theta_min      2.264
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    1.741
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1202 before and 0.0938 after correction.
The Ratio of minimum to maximum transmission is 0.8330.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_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  0.0751
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                3795
_reflns_number_total             4494
_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       ?
_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         0.447
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+1.7431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C1(H1A,H1B), C4(H4A,H4B), C7(H7A,H7B), C5(H5A,H5B), C8(H8A,
 H8B), C2(H2A,H2B), C11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), 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 0.78210(2) 0.59335(2) 0.65812(2) 0.02252(7) Uani 1 1 d . . . . .
Cl1 Cl 0.72036(4) 0.67483(4) 0.75820(3) 0.02648(14) Uani 1 1 d . . . . .
Cl2 Cl 0.76789(5) 0.66911(5) 0.54394(4) 0.04065(18) Uani 1 1 d . . . . .
Cl4 Cl 0.94879(5) 0.56750(5) 0.68047(5) 0.04213(19) Uani 1 1 d . . . . .
Cl3 Cl 0.69188(6) 0.47334(5) 0.64492(4) 0.04242(19) Uani 1 1 d . . . . .
N1 N 0.47361(14) 0.80376(11) 0.63883(10) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.40753(17) 0.87701(14) 0.62716(13) 0.0185(5) Uani 1 1 d . . . . .
H10A H 0.441970 0.925534 0.647217 0.022 Uiso 1 1 calc R U . . .
H10B H 0.398764 0.885058 0.571271 0.022 Uiso 1 1 calc R U . . .
C1 C 0.48617(17) 0.78511(14) 0.72380(12) 0.0178(5) Uani 1 1 d . . . . .
H1A H 0.421640 0.768961 0.744708 0.021 Uiso 1 1 calc R U . . .
H1B H 0.530242 0.737596 0.728709 0.021 Uiso 1 1 calc R U . . .
C4 C 0.42830(17) 0.73001(14) 0.60082(13) 0.0186(5) Uani 1 1 d . . . . .
H4A H 0.364937 0.718522 0.626194 0.022 Uiso 1 1 calc R U . . .
H4B H 0.414220 0.743684 0.546597 0.022 Uiso 1 1 calc R U . . .
C7 C 0.57258(17) 0.82451(15) 0.60355(12) 0.0192(5) Uani 1 1 d . . . . .
H7A H 0.594051 0.877918 0.623666 0.023 Uiso 1 1 calc R U . . .
H7B H 0.620946 0.783439 0.620527 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2553(2) 0.95425(16) 0.64596(15) 0.0283(6) Uani 1 1 d . . . . .
H12A H 0.246173 0.959337 0.590376 0.042 Uiso 1 1 calc R U . . .
H12B H 0.295316 0.999629 0.664585 0.042 Uiso 1 1 calc R U . . .
H12C H 0.191396 0.955280 0.671484 0.042 Uiso 1 1 calc R U . . .
C5 C 0.48946(18) 0.65325(15) 0.60248(14) 0.0245(5) Uani 1 1 d . . . . .
H5A H 0.502739 0.637498 0.656330 0.029 Uiso 1 1 calc R U . . .
H5B H 0.552943 0.663166 0.576714 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4354(2) 0.58523(15) 0.56200(15) 0.0289(6) Uani 1 1 d . . . . .
H6A H 0.426610 0.599373 0.507796 0.043 Uiso 1 1 calc R U . . .
H6B H 0.371233 0.577448 0.586055 0.043 Uiso 1 1 calc R U . . .
H6C H 0.473415 0.534854 0.565959 0.043 Uiso 1 1 calc R U . . .
C8 C 0.57344(18) 0.82793(17) 0.51636(13) 0.0266(6) Uani 1 1 d . . . . .
H8A H 0.569056 0.772104 0.495366 0.032 Uiso 1 1 calc R U . . .
H8B H 0.515850 0.858933 0.498077 0.032 Uiso 1 1 calc R U . . .
C2 C 0.52633(18) 0.85281(16) 0.77313(13) 0.0241(5) Uani 1 1 d . . . . .
H2A H 0.484025 0.901501 0.768995 0.029 Uiso 1 1 calc R U . . .
H2B H 0.593023 0.867648 0.755839 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6664(2) 0.86825(18) 0.48770(14) 0.0332(6) Uani 1 1 d . . . . .
H9A H 0.668582 0.865440 0.431541 0.050 Uiso 1 1 calc R U . . .
H9B H 0.723428 0.840045 0.509092 0.050 Uiso 1 1 calc R U . . .
H9C H 0.667284 0.925295 0.503965 0.050 Uiso 1 1 calc R U . . .
C11 C 0.30699(18) 0.87383(16) 0.66383(13) 0.0232(5) Uani 1 1 d . . . . .
H11A H 0.313063 0.866479 0.720024 0.028 Uiso 1 1 calc R U . . .
H11B H 0.268996 0.827675 0.642755 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5293(2) 0.82300(18) 0.85643(13) 0.0291(6) Uani 1 1 d . . . . .
H3A H 0.567158 0.772482 0.859306 0.044 Uiso 1 1 calc R U . . .
H3B H 0.462398 0.812987 0.874489 0.044 Uiso 1 1 calc R U . . .
H3C H 0.560138 0.864476 0.888780 0.044 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 Cl1 2.3552(6) . ?
In1 Cl2 2.3551(7) . ?
In1 Cl4 2.3486(8) . ?
In1 Cl3 2.3378(8) . ?
N1 C10 1.519(3) . ?
N1 C1 1.521(3) . ?
N1 C4 1.514(3) . ?
N1 C7 1.524(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.514(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.531(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
Cl1 In1 Cl2 107.15(3) . . ?
Cl4 In1 Cl1 109.11(3) . . ?
Cl4 In1 Cl2 108.40(3) . . ?
Cl3 In1 Cl1 111.36(3) . . ?
Cl3 In1 Cl2 108.66(3) . . ?
Cl3 In1 Cl4 112.00(3) . . ?
C10 N1 C1 110.92(17) . . ?
C10 N1 C7 107.19(17) . . ?
C1 N1 C7 109.74(16) . . ?
C4 N1 C10 109.50(17) . . ?
C4 N1 C1 108.07(17) . . ?
C4 N1 C7 111.44(17) . . ?
N1 C10 H10A 108.0 . . ?
N1 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 N1 117.05(19) . . ?
C11 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
N1 C1 H1A 108.2 . . ?
N1 C1 H1B 108.2 . . ?
H1A C1 H1B 107.3 . . ?
C2 C1 N1 116.51(19) . . ?
C2 C1 H1A 108.2 . . ?
C2 C1 H1B 108.2 . . ?
N1 C4 H4A 108.4 . . ?
N1 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 N1 115.71(18) . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
N1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 N1 114.73(19) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.7(2) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.6(2) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C1 C2 C3 108.2(2) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C11 C12 107.6(2) . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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
N1 C10 C11 C12 178.72(19) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
N1 C4 C5 C6 -179.54(19) . . . . ?
N1 C7 C8 C9 166.3(2) . . . . ?
C10 N1 C1 C2 -57.3(3) . . . . ?
C10 N1 C4 C5 175.67(18) . . . . ?
C10 N1 C7 C8 -71.0(2) . . . . ?
C1 N1 C10 C11 -55.0(3) . . . . ?
C1 N1 C4 C5 -63.4(2) . . . . ?
C1 N1 C7 C8 168.4(2) . . . . ?
C4 N1 C10 C11 64.2(2) . . . . ?
C4 N1 C1 C2 -177.30(19) . . . . ?
C4 N1 C7 C8 48.8(3) . . . . ?
C7 N1 C10 C11 -174.77(19) . . . . ?
C7 N1 C1 C2 61.0(2) . . . . ?
C7 N1 C4 C5 57.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
