# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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. 
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data_wr1107_0m
_database_code_depnum_ccdc_archive 'CCDC 2281746'
loop_
_audit_author_name
_audit_author_address
'Rui Wang'
;Ocean University of China
China
;
_audit_update_record             
;
2023-07-15 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H24 In1 N3 O9'
_chemical_formula_sum            'C33 H24 In N3 O9'
_chemical_formula_weight         721.37
_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'
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      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                   13.8174(3)
_cell_length_b                   13.8174(3)
_cell_length_c                   26.1691(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4326.9(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.303
_cell_measurement_theta_min      2.335
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0500 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8748. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2184
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5827
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.981
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1749
_reflns_number_total             1936
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.123
_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)+(0.0124P)²+16.7891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C6(H6), C9(H9), C8(H8), C7(H7)
3.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.333333 0.666667 0.54740(2) 0.02435(11) Uani 1 3 d S T P . .
O1 O 0.47325(15) 0.69302(15) 0.50101(7) 0.0267(4) Uani 1 1 d . . . . .
O3 O 0.67044(17) 0.57224(17) 0.53164(7) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.709930 0.544891 0.522382 0.045 Uiso 1 1 calc GR . . . .
O2 O 0.42892(18) 0.6234(2) 0.59653(8) 0.0398(5) Uani 1 1 d . . . . .
N1 N 0.53731(19) 0.6600(2) 0.52767(9) 0.0246(5) Uani 1 1 d D . . . .
C2 C 0.5847(2) 0.5966(2) 0.60555(10) 0.0244(6) Uani 1 1 d . . . . .
C3 C 0.6602(2) 0.5666(2) 0.58361(10) 0.0250(6) Uani 1 1 d . . . . .
C1 C 0.5131(2) 0.6267(2) 0.57538(10) 0.0272(6) Uani 1 1 d . . . . .
C11 C 0.5756(2) 0.5990(2) 0.65796(11) 0.0293(6) Uani 1 1 d . . . . .
H11 H 0.524679 0.618735 0.672292 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6401(2) 0.5729(2) 0.69062(11) 0.0296(6) Uani 1 1 d . . . . .
C4 C 0.7204(2) 0.5361(2) 0.61438(11) 0.0290(6) Uani 1 1 d . . . . .
H4 H 0.767809 0.512435 0.599487 0.035 Uiso 1 1 calc R . . . .
C5 C 0.7127(2) 0.5394(2) 0.66826(11) 0.0303(6) Uani 1 1 d . . . . .
C6 C 0.7764(3) 0.5111(3) 0.70130(12) 0.0399(8) Uani 1 1 d . . . . .
H6 H 0.825380 0.488336 0.687295 0.048 Uiso 1 1 calc R . . . .
C9 C 0.6343(3) 0.5782(3) 0.74471(12) 0.0408(8) Uani 1 1 d . . . . .
H9 H 0.586319 0.600732 0.759913 0.049 Uiso 1 1 calc R . . . .
C8 C 0.6977(3) 0.5508(3) 0.77478(13) 0.0472(9) Uani 1 1 d . . . . .
H8 H 0.694231 0.555259 0.810901 0.057 Uiso 1 1 calc R . . . .
C7 C 0.7677(3) 0.5163(3) 0.75278(13) 0.0473(9) Uani 1 1 d . . . . .
H7 H 0.810033 0.496105 0.774336 0.057 Uiso 1 1 calc R . . . .
H1 H 0.586(2) 0.652(2) 0.5115(10) 0.028(8) Uiso 1 1 d D . . . .


_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 O1 2.1540(19) . ?
In1 O1 2.1540(19) 2_665 ?
In1 O1 2.1540(19) 3_565 ?
In1 O2 2.132(2) 3_565 ?
In1 O2 2.132(2) . ?
In1 O2 2.132(2) 2_665 ?
O1 N1 1.372(3) . ?
O3 H3 0.8400 . ?
O3 C3 1.365(3) . ?
O2 C1 1.268(3) . ?
N1 C1 1.315(3) . ?
N1 H1 0.855(17) . ?
C2 C3 1.423(4) . ?
C2 C1 1.479(4) . ?
C2 C11 1.379(4) . ?
C3 C4 1.366(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.405(4) . ?
C10 C5 1.425(4) . ?
C10 C9 1.422(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(4) . ?
C5 C6 1.421(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.358(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.363(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.398(5) . ?
C7 H7 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
O1 In1 O1 91.35(7) . 3_565 ?
O1 In1 O1 91.36(7) 2_665 . ?
O1 In1 O1 91.35(7) 2_665 3_565 ?
O2 In1 O1 153.93(8) . 2_665 ?
O2 In1 O1 111.33(8) . 3_565 ?
O2 In1 O1 153.93(8) 3_565 . ?
O2 In1 O1 75.99(7) 2_665 2_665 ?
O2 In1 O1 111.34(8) 2_665 . ?
O2 In1 O1 75.98(7) . . ?
O2 In1 O1 153.93(8) 2_665 3_565 ?
O2 In1 O1 111.33(8) 3_565 2_665 ?
O2 In1 O1 75.99(7) 3_565 3_565 ?
O2 In1 O2 87.37(8) 3_565 . ?
O2 In1 O2 87.37(8) 2_665 . ?
O2 In1 O2 87.37(8) 2_665 3_565 ?
N1 O1 In1 109.33(14) . . ?
C3 O3 H3 109.5 . . ?
C1 O2 In1 114.34(18) . . ?
O1 N1 H1 119(2) . . ?
C1 N1 O1 120.3(2) . . ?
C1 N1 H1 120(2) . . ?
C3 C2 C1 123.9(2) . . ?
C11 C2 C3 119.8(3) . . ?
C11 C2 C1 116.3(2) . . ?
O3 C3 C2 117.1(2) . . ?
O3 C3 C4 122.9(3) . . ?
C4 C3 C2 120.0(3) . . ?
O2 C1 N1 119.7(3) . . ?
O2 C1 C2 119.2(2) . . ?
N1 C1 C2 121.1(2) . . ?
C2 C11 H11 119.3 . . ?
C2 C11 C10 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C11 C10 C5 118.3(3) . . ?
C11 C10 C9 122.3(3) . . ?
C9 C10 C5 119.5(3) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C10 119.7(3) . . ?
C4 C5 C6 122.0(3) . . ?
C6 C5 C10 118.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
