# 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 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220901h_0m
_database_code_depnum_ccdc_archive 'CCDC 2239710'
loop_
_audit_author_name
_audit_author_address
'Shuya Jin'
;GuangXi University
China
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
"tris(N,N'-Diphenylquanidinum) hexabromoindium(iii)"
_chemical_formula_moiety         'Br6 In1, 3(C13 H14 N3)'
_chemical_formula_sum            'C39 H42 Br6 In N9'
_chemical_formula_weight         1231.09
_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           148
_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'
'-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                   16.613(3)
_cell_length_b                   16.613
_cell_length_c                   14.280(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3413.1(13)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2505
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.700
_cell_measurement_theta_min      2.452
_shelx_estimated_absorpt_T_max   0.593
_shelx_estimated_absorpt_T_min   0.518
_exptl_absorpt_coefficient_mu    5.826
_exptl_absorpt_correction_T_max  0.0469
_exptl_absorpt_correction_T_min  0.0180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0335 after correction.
The Ratio of minimum to maximum transmission is 0.3838.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1794
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         3.171
_diffrn_ambient_temperature      296.15
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1332
_reflns_number_total             1740
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1740
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      0.995
_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)+(0.0363P)²+6.5891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2. Others
 Fixed Sof: C7(0.5) N2(0.5) H2(0.5) N1(0.5) H1(0.5) C9(0.5) H9(0.5) C8(0.5)
 C13(0.5) H13(0.5) C12(0.5) H12(0.5) C11(0.5) H11(0.5) C10(0.5) H10(0.5)
 N3(0.5) H3A(0.5) H3B(0.5) C6(0.5) C5(0.5) H5(0.5) C4(0.5) H4(0.5) C3(0.5)
 H3(0.5) C2(0.5) H2A(0.5) C1(0.5) H1A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C13(H13), C12(H12), C11(H11), C10(H10), C5(H5),
 C4(H4), C3(H3), C2(H2A), C1(H1A)
3.b Fitted hexagon refined as free rotating group:
 C9(C8,C13,C12,C11,C10), C6(C5,C4,C3,C2,C1)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_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 0.333333 0.666667 0.666667 0.04717(16) Uani 1 6 d S T P . .
Br1 Br 0.26847(2) 0.51289(2) 0.56199(2) 0.05789(14) Uani 1 1 d . . . . .
C7 C 0.4981(16) 0.5114(11) 0.5039(13) 0.050(2) Uani 0.5 1 d . . P A -1
N2 N 0.4694(5) 0.4886(5) 0.5907(5) 0.0692(17) Uani 0.5 1 d . . P A -1
H2 H 0.457499 0.527138 0.621924 0.083 Uiso 0.5 1 calc R U P A -1
N1 N 0.5067(5) 0.5910(4) 0.4704(5) 0.0712(17) Uani 0.5 1 d . . P A -1
H1 H 0.493395 0.623262 0.510096 0.085 Uiso 0.5 1 calc R U P A -1
C9 C 0.5294(4) 0.3926(5) 0.6539(6) 0.076(2) Uani 0.5 1 d G . P A -1
H9 H 0.588557 0.433471 0.627399 0.092 Uiso 0.5 1 calc R U P A -1
C8 C 0.4555(5) 0.4080(4) 0.6390(4) 0.0593(18) Uani 0.5 1 d G . P A -1
C13 C 0.3690(4) 0.3482(6) 0.6778(7) 0.091(4) Uani 0.5 1 d G . P A -1
H13 H 0.318492 0.358666 0.667553 0.110 Uiso 0.5 1 calc R U P A -1
C12 C 0.3564(6) 0.2730(6) 0.7315(8) 0.120(6) Uani 0.5 1 d G . P A -1
H12 H 0.297264 0.232079 0.758058 0.144 Uiso 0.5 1 calc R U P A -1
C11 C 0.4303(7) 0.2576(5) 0.7465(7) 0.109(4) Uani 0.5 1 d G . P A -1
H11 H 0.421682 0.206188 0.783234 0.130 Uiso 0.5 1 calc R U P A -1
C10 C 0.5168(6) 0.3174(6) 0.7077(7) 0.086(3) Uani 0.5 1 d G . P A -1
H10 H 0.567328 0.306882 0.717905 0.103 Uiso 0.5 1 calc R U P A -1
N3 N 0.5157(5) 0.4576(4) 0.4490(5) 0.0608(15) Uani 0.5 1 d . . P A -1
H3A H 0.508113 0.404548 0.470376 0.073 Uiso 0.5 1 calc R U P A -1
H3B H 0.534855 0.474893 0.391170 0.073 Uiso 0.5 1 calc R U P A -1
C6 C 0.5337(5) 0.6290(4) 0.3812(4) 0.0617(18) Uani 0.5 1 d G . P A -1
C5 C 0.6214(6) 0.6556(7) 0.3457(7) 0.098(5) Uani 0.5 1 d G . P A -1
H5 H 0.660515 0.637793 0.377221 0.118 Uiso 0.5 1 calc R U P A -1
C4 C 0.6520(6) 0.7081(8) 0.2642(8) 0.111(5) Uani 0.5 1 d G . P A -1
H4 H 0.711904 0.726199 0.239932 0.133 Uiso 0.5 1 calc R U P A -1
C3 C 0.5948(7) 0.7341(7) 0.2181(6) 0.115(5) Uani 0.5 1 d G . P A -1
H3 H 0.615635 0.769957 0.162371 0.138 Uiso 0.5 1 calc R U P A -1
C2 C 0.5071(7) 0.7075(8) 0.2536(5) 0.105(4) Uani 0.5 1 d G . P A -1
H2A H 0.467977 0.725310 0.222098 0.126 Uiso 0.5 1 calc R U P A -1
C1 C 0.4765(4) 0.6550(7) 0.3351(5) 0.084(3) Uani 0.5 1 d G . P A -1
H1A H 0.416585 0.636905 0.359388 0.100 Uiso 0.5 1 calc R 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 Br1 2.6775(4) 3_565 ?
In1 Br1 2.6776(5) 14_456 ?
In1 Br1 2.6775(5) 2_665 ?
In1 Br1 2.6775(4) . ?
In1 Br1 2.6776(3) 13_566 ?
In1 Br1 2.6774(4) 15_556 ?
C7 N2 1.314(19) . ?
C7 N1 1.346(15) . ?
C7 N3 1.326(14) . ?
N2 H2 0.8800 . ?
N2 C8 1.419(9) . ?
N1 H1 0.8800 . ?
N1 C6 1.393(8) . ?
C9 H9 0.9500 . ?
C9 C8 1.3900 . ?
C9 C10 1.3900 . ?
C8 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C12 1.3900 . ?
C12 H12 0.9500 . ?
C12 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 C10 1.3900 . ?
C10 H10 0.9500 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C6 C5 1.3900 . ?
C6 C1 1.3900 . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C2 1.3900 . ?
C2 H2A 0.9500 . ?
C2 C1 1.3900 . ?
C1 H1A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 In1 Br1 180.0 3_565 15_556 ?
Br1 In1 Br1 91.859(12) 14_456 13_566 ?
Br1 In1 Br1 88.140(13) 14_456 . ?
Br1 In1 Br1 88.140(13) 2_665 13_566 ?
Br1 In1 Br1 88.139(13) 15_556 . ?
Br1 In1 Br1 91.862(13) 2_665 . ?
Br1 In1 Br1 180.0 13_566 . ?
Br1 In1 Br1 91.861(16) 3_565 2_665 ?
Br1 In1 Br1 91.863(17) 15_556 14_456 ?
Br1 In1 Br1 91.862(13) 3_565 . ?
Br1 In1 Br1 180.0 2_665 14_456 ?
Br1 In1 Br1 88.140(17) 15_556 2_665 ?
Br1 In1 Br1 88.136(13) 3_565 13_566 ?
Br1 In1 Br1 91.863(13) 15_556 13_566 ?
Br1 In1 Br1 88.136(17) 3_565 14_456 ?
N2 C7 N1 117.5(10) . . ?
N2 C7 N3 122.3(11) . . ?
N3 C7 N1 120.1(14) . . ?
C7 N2 H2 116.8 . . ?
C7 N2 C8 126.4(7) . . ?
C8 N2 H2 116.8 . . ?
C7 N1 H1 115.8 . . ?
C7 N1 C6 128.4(9) . . ?
C6 N1 H1 115.8 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C8 N2 120.5(6) . . ?
C9 C8 C13 120.0 . . ?
C13 C8 N2 119.3(6) . . ?
C8 C13 H13 120.0 . . ?
C8 C13 C12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C5 C6 N1 121.8(6) . . ?
C5 C6 C1 120.0 . . ?
C1 C6 N1 117.3(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1A 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
C7 N2 C8 C9 61.5(16) . . . . ?
C7 N2 C8 C13 -123.6(15) . . . . ?
C7 N1 C6 C5 -62.4(16) . . . . ?
C7 N1 C6 C1 128.8(14) . . . . ?
N2 C7 N1 C6 -178.6(12) . . . . ?
N2 C8 C13 C12 -174.9(7) . . . . ?
N1 C7 N2 C8 179.8(11) . . . . ?
N1 C6 C5 C4 -168.5(7) . . . . ?
N1 C6 C1 C2 169.0(7) . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C8 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C10 C9 C8 N2 174.9(7) . . . . ?
C10 C9 C8 C13 0.0 . . . . ?
N3 C7 N2 C8 2(3) . . . . ?
N3 C7 N1 C6 -1(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
_exptl_crystal_preparation       Luminescent
