# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_23te06034
_audit_block_doi                 10.5517/ccdc.csd.cc2j4rp4
_database_code_depnum_ccdc_archive 'CCDC 2328276'
loop_
_audit_author_name
_audit_author_address
'Chunqing Hou'
;Jilin University
China
;
_audit_update_record             
;
2024-01-25 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_audit_creation_date             2023-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 In1, 3(C13 H14 N3)'
_chemical_formula_sum            'C39 H42 Br6 In N9'
_chemical_formula_weight         1231.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   16.492(2)
_cell_length_b                   16.492(2)
_cell_length_c                   14.152(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3333.6(13)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4701
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.965
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       B
_exptl_crystal_F_000             1794
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26582
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         3.195
_diffrn_ambient_temperature      220.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1944
_reflns_number_total             3408
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.584
_refine_diff_density_min         -1.360
_refine_diff_density_rms         0.209
_refine_ls_abs_structure_details 
;
 Flack x determined using 794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.51(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.067
_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)+(0.1312P)²+83.4651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N006-C005 = N006-C00B
 1.48 with sigma of 0.02
 N1-C00D = N1-C005 = N006-C005 = N006-C00B
 1.48 with sigma of 0.02
 N2-C005
 1.35 with sigma of 0.02
 H006-N006
 1 with sigma of 0.02
 N006-H006
 0.8 with sigma of 0.02
 N2-C00D \\sim N2-C00B
 with sigma of 0.02
 H006-C005 \\sim H006-C00B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C00D) = Uanis(C00G) = Uanis(C009) = Uanis(C00K) = Uanis(C00A) =
Uanis(C007) = Uanis(C00H) = Uanis(C00B) = Uanis(C008) = Uanis(C00E) =
Uanis(C00C) = Uanis(C00J)
Uanis(N2) = Uanis(N006) = Uanis(N1)
4.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00G(H00G), C009(H009), C00K(H00K), C00A(H00A), C008(H008),
 C00H(H00H), C00J(H00J), C00E(H00E), C00C(H00C), N1(H1)
4.b Fitted hexagon refined as free rotating group:
 C007(C00D,C00G,C009,C00K,C00A), C008(C00B,C00H,C00J,C00E,C00C)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
In00 In 0.666667 0.333333 0.6735(4) 0.0504(6) Uani 1 3 d S T P . .
Br1 Br 0.7302(2) 0.4879(2) 0.77844(14) 0.0566(11) Uani 1 1 d . . . . .
Br Br 0.5759(2) 0.3974(2) 0.56677(12) 0.0548(10) Uani 1 1 d . . . . .
C005 C 0.838(2) 0.6758(19) 0.507(2) 0.070(7) Uani 1 1 d D . . . .
N006 N 0.9296(15) 0.7542(15) 0.5349(13) 0.071(4) Uani 1 1 d D . . . .
H006 H 0.966(9) 0.796(12) 0.490(5) 0.085 Uiso 1 1 d D U . . .
C007 C 0.6825(14) 0.6453(10) 0.3312(15) 0.080(2) Uani 1 1 d G . . . .
H007 H 0.694271 0.706449 0.342140 0.097 Uiso 1 1 calc R U . . .
C00D C 0.7380(13) 0.6145(12) 0.3744(15) 0.080(2) Uani 1 1 d DG . . . .
C00G C 0.7207(14) 0.5240(13) 0.3583(17) 0.080(2) Uani 1 1 d G . . . .
H00G H 0.758154 0.503220 0.387464 0.097 Uiso 1 1 calc R U . . .
C009 C 0.6479(15) 0.4644(10) 0.2990(17) 0.080(2) Uani 1 1 d G . . . .
H009 H 0.636149 0.403251 0.288051 0.097 Uiso 1 1 calc R U . . .
C00K C 0.5924(13) 0.4952(12) 0.2558(15) 0.080(2) Uani 1 1 d G . . . .
H00K H 0.543204 0.454881 0.215682 0.097 Uiso 1 1 calc R U . . .
C00A C 0.6098(13) 0.5856(13) 0.2719(15) 0.080(2) Uani 1 1 d G . . . .
H00A H 0.572263 0.606479 0.242725 0.097 Uiso 1 1 calc R U . . .
C008 C 0.9929(16) 0.7036(11) 0.6651(15) 0.080(2) Uani 1 1 d G . . . .
H008 H 0.973781 0.646002 0.634940 0.097 Uiso 1 1 calc R U . . .
C00B C 0.9623(14) 0.7629(13) 0.6316(13) 0.080(2) Uani 1 1 d DG . . . .
C00H C 0.9906(15) 0.8481(12) 0.6762(15) 0.080(2) Uani 1 1 d G . . . .
H00H H 0.969862 0.888198 0.653569 0.097 Uiso 1 1 calc R U . . .
C00J C 1.0494(15) 0.8738(11) 0.7543(15) 0.080(2) Uani 1 1 d G . . . .
H00J H 1.068542 0.931372 0.784473 0.097 Uiso 1 1 calc R U . . .
C00E C 1.0800(13) 0.8144(13) 0.7878(13) 0.080(2) Uani 1 1 d G . . . .
H00E H 1.119840 0.831861 0.840614 0.097 Uiso 1 1 calc R U . . .
C00C C 1.0518(15) 0.7293(12) 0.7432(15) 0.080(2) Uani 1 1 d G . . . .
H00C H 1.072462 0.689176 0.765848 0.097 Uiso 1 1 calc R U . . .
N1 N 0.8287(15) 0.6863(14) 0.4146(15) 0.071(4) Uani 1 1 d D . . . .
H1 H 0.872053 0.731310 0.381038 0.085 Uiso 1 1 calc R U . . .
N2 N 0.7926(14) 0.6098(15) 0.5646(14) 0.071(4) Uani 1 1 d D . . . .
H2A H 0.744076 0.558288 0.545424 0.085 Uiso 1 1 calc R U . . .
H2B H 0.809821 0.615935 0.623536 0.085 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
In00 Br1 2.671(4) 3_665 ?
In00 Br1 2.670(4) 2_655 ?
In00 Br1 2.671(4) . ?
In00 Br 2.687(4) . ?
In00 Br 2.687(4) 3_665 ?
In00 Br 2.687(4) 2_655 ?
C005 N006 1.466(19) . ?
C005 N1 1.34(2) . ?
C005 N2 1.27(2) . ?
N006 H006 0.90(2) . ?
N006 C00B 1.452(16) . ?
C007 H007 0.9400 . ?
C007 C00D 1.3900 . ?
C007 C00A 1.3900 . ?
C00D C00G 1.3900 . ?
C00D N1 1.48(2) . ?
C00G H00G 0.9400 . ?
C00G C009 1.3900 . ?
C009 H009 0.9400 . ?
C009 C00K 1.3900 . ?
C00K H00K 0.9400 . ?
C00K C00A 1.3900 . ?
C00A H00A 0.9400 . ?
C008 H008 0.9400 . ?
C008 C00B 1.3900 . ?
C008 C00C 1.3900 . ?
C00B C00H 1.3900 . ?
C00H H00H 0.9400 . ?
C00H C00J 1.3900 . ?
C00J H00J 0.9400 . ?
C00J C00E 1.3900 . ?
C00E H00E 0.9400 . ?
C00E C00C 1.3900 . ?
C00C H00C 0.9400 . ?
N1 H1 0.8700 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?

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 In00 Br1 92.08(17) 3_665 2_655 ?
Br1 In00 Br1 92.08(17) 3_665 . ?
Br1 In00 Br1 92.08(17) 2_655 . ?
Br1 In00 Br 179.5(2) 2_655 3_665 ?
Br1 In00 Br 88.33(11) . 3_665 ?
Br1 In00 Br 88.11(11) 2_655 2_655 ?
Br1 In00 Br 88.33(11) 2_655 . ?
Br1 In00 Br 88.11(11) 3_665 3_665 ?
Br1 In00 Br 179.5(2) . 2_655 ?
Br1 In00 Br 88.11(11) . . ?
Br1 In00 Br 179.5(2) 3_665 . ?
Br1 In00 Br 88.33(11) 3_665 2_655 ?
Br In00 Br 91.48(16) 2_655 . ?
Br In00 Br 91.48(16) 3_665 . ?
Br In00 Br 91.48(16) 2_655 3_665 ?
N1 C005 N006 107(2) . . ?
N2 C005 N006 119(2) . . ?
N2 C005 N1 133(2) . . ?
C005 N006 H006 119(2) . . ?
C00B N006 C005 120.6(18) . . ?
C00B N006 H006 120(2) . . ?
C00D C007 H007 120.0 . . ?
C00D C007 C00A 120.0 . . ?
C00A C007 H007 120.0 . . ?
C007 C00D C00G 120.0 . . ?
C007 C00D N1 117.6(14) . . ?
C00G C00D N1 120.3(14) . . ?
C00D C00G H00G 120.0 . . ?
C00D C00G C009 120.0 . . ?
C009 C00G H00G 120.0 . . ?
C00G C009 H009 120.0 . . ?
C00K C009 C00G 120.0 . . ?
C00K C009 H009 120.0 . . ?
C009 C00K H00K 120.0 . . ?
C00A C00K C009 120.0 . . ?
C00A C00K H00K 120.0 . . ?
C007 C00A H00A 120.0 . . ?
C00K C00A C007 120.0 . . ?
C00K C00A H00A 120.0 . . ?
C00B C008 H008 120.0 . . ?
C00B C008 C00C 120.0 . . ?
C00C C008 H008 120.0 . . ?
C008 C00B N006 119.9(16) . . ?
C00H C00B N006 116.7(15) . . ?
C00H C00B C008 120.0 . . ?
C00B C00H H00H 120.0 . . ?
C00B C00H C00J 120.0 . . ?
C00J C00H H00H 120.0 . . ?
C00H C00J H00J 120.0 . . ?
C00E C00J C00H 120.0 . . ?
C00E C00J H00J 120.0 . . ?
C00J C00E H00E 120.0 . . ?
C00C C00E C00J 120.0 . . ?
C00C C00E H00E 120.0 . . ?
C008 C00C H00C 120.0 . . ?
C00E C00C C008 120.0 . . ?
C00E C00C H00C 120.0 . . ?
C005 N1 C00D 114.2(19) . . ?
C005 N1 H1 122.9 . . ?
C00D N1 H1 122.9 . . ?
C005 N2 H2A 120.0 . . ?
C005 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C005 N006 C00B C008 74(3) . . . . ?
C005 N006 C00B C00H -127(2) . . . . ?
N006 C005 N1 C00D -178(2) . . . . ?
N006 C00B C00H C00J -159(2) . . . . ?
C007 C00D C00G C009 0.0 . . . . ?
C007 C00D N1 C005 122(2) . . . . ?
C00D C007 C00A C00K 0.0 . . . . ?
C00D C00G C009 C00K 0.0 . . . . ?
C00G C00D N1 C005 -75(3) . . . . ?
C00G C009 C00K C00A 0.0 . . . . ?
C009 C00K C00A C007 0.0 . . . . ?
C00A C007 C00D C00G 0.0 . . . . ?
C00A C007 C00D N1 164(2) . . . . ?
C008 C00B C00H C00J 0.0 . . . . ?
C00B C008 C00C C00E 0.0 . . . . ?
C00B C00H C00J C00E 0.0 . . . . ?
C00H C00J C00E C00C 0.0 . . . . ?
C00J C00E C00C C008 0.0 . . . . ?
C00C C008 C00B N006 159(2) . . . . ?
C00C C008 C00B C00H 0.0 . . . . ?
N1 C005 N006 C00B -179(2) . . . . ?
N1 C00D C00G C009 -163(2) . . . . ?
N2 C005 N006 C00B -8(5) . . . . ?
N2 C005 N1 C00D 13(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
