# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1_sq
_audit_block_doi                 10.5517/ccdc.csd.cc27t0kn
_database_code_depnum_ccdc_archive 'CCDC 2079621'
loop_
_audit_author_name
_audit_author_address
'Jin Jing'
;Northwest university
China
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2022-06-03 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 In N O5'
_chemical_formula_sum            'C10 H5 In N O5'
_chemical_formula_weight         333.97
_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'
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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   21.661(6)
_cell_length_b                   23.081(5)
_cell_length_c                   13.499(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6749(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9740
_cell_measurement_temperature    179.97
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1621 before and 0.0866 after correction.
The Ratio of minimum to maximum transmission is 0.7312.
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22809
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.587
_diffrn_reflns_theta_min         2.579
_diffrn_ambient_temperature      179.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_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           1.4
_diffrn_source_power             0.07
_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                2284
_reflns_number_total             3216
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.484
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.138
_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)+(0.0875P)²+24.1644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1708
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C10-C3 = C8-C3 = C9-C8 = C10-C7
 1.39 with sigma of 0.01
3. Rigid bond restraints
 C14, C11, N1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5) C10(0.5) C13(0.5)
 C14(0.5) H14(0.5) N1(0.5) C11(0.5) H11(0.5) N2(0.5) C12(0.5) H12(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C11(H11), C12(H12)
6.b Fitted hexagon refined as free rotating group:
 C13(C14,N1,C11,N2,C12)
;
_atom_sites_solution_hydrogens   geom
_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
In1 In 0.750000 0.250000 0.500000 0.0287(2) Uani 1 2 d S . P . .
In2 In 0.750000 0.30355(2) 0.250000 0.0307(2) Uani 1 2 d S T P . .
O1 O 0.7211(2) 0.24345(14) 0.3541(2) 0.0396(10) Uani 1 1 d . . . . .
O2 O 0.7223(2) 0.37389(15) 0.3436(3) 0.0452(10) Uani 1 1 d . . . . .
O3 O 0.7416(2) 0.34332(18) 0.4975(3) 0.0496(13) Uani 1 1 d . . . . .
O4 O 0.6589(2) 0.19037(17) 0.6873(3) 0.0485(11) Uani 1 1 d . . . . .
O5 O 0.6567(2) 0.24271(19) 0.5474(3) 0.0533(12) Uani 1 1 d . . . . .
C1 C 0.7296(3) 0.3814(2) 0.4345(4) 0.0362(13) Uani 1 1 d . . . . .
C2 C 0.6312(3) 0.2151(2) 0.6173(4) 0.0426(15) Uani 1 1 d . . . . .
C3 C 0.7266(3) 0.4426(2) 0.4695(4) 0.0406(14) Uani 1 1 d D . . . .
C4 C 0.5636(3) 0.2125(3) 0.6175(4) 0.0451(15) Uani 1 1 d . . . . .
C5 C 0.5308(4) 0.1765(4) 0.6777(6) 0.084(3) Uani 1 1 d . . . . .
H5 H 0.552206 0.150877 0.720627 0.101 Uiso 1 1 calc R U . . .
C6 C 0.5310(4) 0.2492(4) 0.5568(7) 0.102(4) Uani 1 1 d . . . . .
H6 H 0.552684 0.274991 0.514337 0.122 Uiso 1 1 calc R U . . .
C7 C 0.7016(9) 0.5148(5) 0.5887(10) 0.048(4) Uani 0.5 1 d D . P A 1
H7 H 0.683846 0.525096 0.650511 0.057 Uiso 0.5 1 calc R U P A 1
C8 C 0.7492(7) 0.4570(4) 0.5632(7) 0.041(3) Uani 0.5 1 d D . P B 2
H8 H 0.765409 0.427809 0.605410 0.049 Uiso 0.5 1 calc R U P B 2
C9 C 0.7479(9) 0.5146(4) 0.5943(10) 0.052(4) Uani 0.5 1 d D . P B 2
H9 H 0.761572 0.524488 0.659006 0.062 Uiso 0.5 1 calc R U P B 2
C10 C 0.7015(8) 0.4571(4) 0.5603(7) 0.041(3) Uani 0.5 1 d D . P A 1
C13 C 0.6689(5) 0.4162(4) 0.6263(6) 0.062(4) Uani 0.5 1 d G . P . .
C14 C 0.6048(5) 0.4138(5) 0.6232(8) 0.127(7) Uani 0.5 1 d G U P B .
H14 H 0.582689 0.437135 0.577290 0.152 Uiso 0.5 1 calc R U P . .
N1 N 0.5730(4) 0.3774(6) 0.6874(10) 0.123(6) Uani 0.5 1 d G U P B .
C11 C 0.6053(5) 0.3433(5) 0.7547(8) 0.105(6) Uani 0.5 1 d G U P B .
H11 H 0.583531 0.318441 0.798550 0.126 Uiso 0.5 1 calc R U P . .
N2 N 0.6694(5) 0.3457(4) 0.7577(6) 0.067(4) Uani 0.5 1 d G . P B .
C12 C 0.7012(4) 0.3821(4) 0.6935(7) 0.073(5) Uani 0.5 1 d G . P B .
H12 H 0.744958 0.383700 0.695608 0.087 Uiso 0.5 1 calc R U P . .


_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 2.072(3) 13_656 ?
In1 O1 2.072(3) . ?
In1 O3 2.162(4) . ?
In1 O3 2.162(4) 13_656 ?
In1 O5 2.126(4) 13_656 ?
In1 O5 2.126(4) . ?
In2 O1 2.071(3) 7_645 ?
In2 O1 2.071(3) . ?
In2 O2 2.143(4) 7_645 ?
In2 O2 2.143(4) . ?
In2 O4 2.152(4) 11_565 ?
In2 O4 2.152(4) 13_656 ?
O2 C1 1.250(6) . ?
O3 C1 1.249(7) . ?
O4 C2 1.256(6) . ?
O5 C2 1.265(7) . ?
C1 C3 1.491(7) . ?
C2 C4 1.466(9) . ?
C3 C7 1.371(15) 4_566 ?
C3 C8 1.397(8) . ?
C3 C9 1.391(15) 4_566 ?
C3 C10 1.382(8) . ?
C4 C5 1.361(9) . ?
C4 C6 1.374(9) . ?
C5 C5 1.333(16) 12_655 ?
C5 H5 0.9500 . ?
C6 C6 1.345(16) 12_655 ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C10 1.385(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(9) . ?
C9 H9 0.9500 . ?
C10 C13 1.479(13) . ?
C13 C14 1.3900 . ?
C13 C12 1.3900 . ?
C14 H14 0.9500 . ?
C14 N1 1.3900 . ?
N1 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 N2 1.3900 . ?
N2 C12 1.3900 . ?
C12 H12 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 180.0 13_656 . ?
O1 In1 O3 91.85(15) 13_656 13_656 ?
O1 In1 O3 88.15(15) . 13_656 ?
O1 In1 O3 91.85(15) . . ?
O1 In1 O3 88.15(15) 13_656 . ?
O1 In1 O5 89.64(17) 13_656 13_656 ?
O1 In1 O5 90.35(17) . 13_656 ?
O1 In1 O5 90.36(17) 13_656 . ?
O1 In1 O5 89.65(17) . . ?
O3 In1 O3 180.0 . 13_656 ?
O5 In1 O3 90.19(17) . . ?
O5 In1 O3 89.81(17) . 13_656 ?
O5 In1 O3 90.19(17) 13_656 13_656 ?
O5 In1 O3 89.81(17) 13_656 . ?
O5 In1 O5 180.0 13_656 . ?
O1 In2 O1 95.9(2) . 7_645 ?
O1 In2 O2 172.72(14) . 7_645 ?
O1 In2 O2 172.71(14) 7_645 . ?
O1 In2 O2 91.31(15) 7_645 7_645 ?
O1 In2 O2 91.31(15) . . ?
O1 In2 O4 93.07(16) 7_645 11_565 ?
O1 In2 O4 93.07(16) . 13_656 ?
O1 In2 O4 91.93(17) . 11_565 ?
O1 In2 O4 91.93(17) 7_645 13_656 ?
O2 In2 O2 81.5(2) . 7_645 ?
O2 In2 O4 85.74(16) 7_645 13_656 ?
O2 In2 O4 85.74(16) . 11_565 ?
O2 In2 O4 88.60(17) 7_645 11_565 ?
O2 In2 O4 88.60(17) . 13_656 ?
O4 In2 O4 172.5(2) 13_656 11_565 ?
In2 O1 In1 120.33(18) . . ?
C1 O2 In2 130.4(4) . . ?
C1 O3 In1 136.7(4) . . ?
C2 O4 In2 134.7(4) . 13_656 ?
C2 O5 In1 132.8(4) . . ?
O2 C1 C3 115.9(5) . . ?
O3 C1 O2 126.7(5) . . ?
O3 C1 C3 117.3(5) . . ?
O4 C2 O5 125.5(6) . . ?
O4 C2 C4 117.2(5) . . ?
O5 C2 C4 117.3(5) . . ?
C7 C3 C1 121.1(6) 4_566 . ?
C7 C3 C9 42.7(7) 4_566 4_566 ?
C7 C3 C10 100.3(8) 4_566 . ?
C8 C3 C1 119.9(6) . . ?
C8 C3 C9 105.9(8) . 4_566 ?
C9 C3 C1 117.6(6) 4_566 . ?
C10 C3 C1 121.9(6) . . ?
C10 C3 C9 120.5(8) . 4_566 ?
C5 C4 C2 123.2(6) . . ?
C5 C4 C6 117.6(7) . . ?
C6 C4 C2 119.1(6) . . ?
C4 C5 H5 119.3 . . ?
C5 C5 C4 121.5(4) 12_655 . ?
C5 C5 H5 119.3 12_655 . ?
C4 C6 H6 119.6 . . ?
C6 C6 C4 120.9(4) 12_655 . ?
C6 C6 H6 119.6 12_655 . ?
C3 C7 H7 118.9 4_566 . ?
C3 C7 C10 122.2(11) 4_566 . ?
C10 C7 H7 118.9 . . ?
C3 C8 H8 120.2 . . ?
C9 C8 C3 119.6(10) . . ?
C9 C8 H8 120.2 . . ?
C3 C9 H9 120.1 4_566 . ?
C8 C9 H9 120.1 . . ?
C3 C10 C7 118.6(9) . . ?
C3 C10 C13 124.6(8) . . ?
C7 C10 C13 116.6(10) . . ?
C14 C13 C10 119.0(9) . . ?
C14 C13 C12 120.0 . . ?
C12 C13 C10 120.9(9) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 N1 120.0 . . ?
N1 C14 H14 120.0 . . ?
C11 N1 C14 120.0 . . ?
N1 C11 H11 120.0 . . ?
N1 C11 N2 120.0 . . ?
N2 C11 H11 120.0 . . ?
C11 N2 C12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N2 C12 C13 120.0 . . ?
N2 C12 H12 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
In1 O3 C1 O2 -5.5(11) . . . . ?
In1 O3 C1 C3 177.7(5) . . . . ?
In1 O5 C2 O4 11.4(9) . . . . ?
In1 O5 C2 C4 -169.8(4) . . . . ?
In2 O2 C1 O3 -19.1(10) . . . . ?
In2 O2 C1 C3 157.7(4) . . . . ?
In2 O4 C2 O5 18.0(9) 13_656 . . . ?
In2 O4 C2 C4 -160.8(4) 13_656 . . . ?
O2 C1 C3 C7 16.4(12) . . . 4_566 ?
O2 C1 C3 C8 -163.9(9) . . . . ?
O2 C1 C3 C9 -32.8(12) . . . 4_566 ?
O2 C1 C3 C10 144.8(10) . . . . ?
O3 C1 C3 C7 -166.4(11) . . . 4_566 ?
O3 C1 C3 C8 13.3(12) . . . . ?
O3 C1 C3 C9 144.4(11) . . . 4_566 ?
O3 C1 C3 C10 -38.1(12) . . . . ?
O4 C2 C4 C5 -12.5(10) . . . . ?
O4 C2 C4 C6 165.2(7) . . . . ?
O5 C2 C4 C5 168.6(7) . . . . ?
O5 C2 C4 C6 -13.7(10) . . . . ?
C1 C3 C8 C9 178.2(12) . . . . ?
C1 C3 C10 C7 178.5(12) . . . . ?
C1 C3 C10 C13 -7.6(19) . . . . ?
C2 C4 C5 C5 178.2(4) . . . 12_655 ?
C2 C4 C6 C6 -178.2(4) . . . 12_655 ?
C3 C7 C10 C3 -1(2) 4_566 . . . ?
C3 C7 C10 C13 -175.4(13) 4_566 . . . ?
C3 C8 C9 C3 -3(2) . . . 4_566 ?
C3 C10 C13 C14 -96.5(14) . . . . ?
C3 C10 C13 C12 86.1(15) . . . . ?
C5 C4 C6 C6 -0.4(9) . . . 12_655 ?
C6 C4 C5 C5 0.4(9) . . . 12_655 ?
C7 C3 C10 C7 -44.5(14) 4_566 . . . ?
C7 C3 C10 C13 129.4(14) 4_566 . . . ?
C7 C10 C13 C14 77.5(16) . . . . ?
C7 C10 C13 C12 -99.9(15) . . . . ?
C9 C3 C8 C9 42.1(14) 4_566 . . . ?
C10 C13 C14 N1 -177.4(9) . . . . ?
C10 C13 C12 N2 177.3(9) . . . . ?
C13 C14 N1 C11 0.0 . . . . ?
C14 C13 C12 N2 0.0 . . . . ?
C14 N1 C11 N2 0.0 . . . . ?
N1 C11 N2 C12 0.0 . . . . ?
C11 N2 C12 C13 0.0 . . . . ?
C12 C13 C14 N1 0.0 . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.002 610 158 ' '
2 0.000 0.500 0.112 610 158 ' '
3 0.500 0.500 0.002 610 158 ' '
4 0.500 0.000 -0.031 610 158 ' '
5 0.000 0.233 0.163 8 2 ' '
6 0.500 0.733 0.163 8 2 ' '
7 0.000 0.733 0.336 8 2 ' '
8 0.500 0.233 0.336 8 2 ' '
9 0.000 0.267 0.663 8 2 ' '
10 0.500 0.767 0.663 8 2 ' '
11 0.000 0.767 0.837 8 2 ' '
12 0.500 0.267 0.837 8 2 ' '

_platon_squeeze_void_probe_radius 1.20
_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_2_sq
_database_code_depnum_ccdc_archive 'CCDC 2109820'
loop_
_audit_author_name
_audit_author_address
'jin jing'
;Northwest University
China
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-03 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_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         'C8 H4 In O5'
_chemical_formula_sum            'C8 H4 In O5'
_chemical_formula_weight         294.93
_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'
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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   21.8718(6)
_cell_length_b                   23.1289(7)
_cell_length_c                   13.5024(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6830.5(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2021
_cell_measurement_temperature    186.0
_cell_measurement_theta_max      24.67
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22232
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.410
_diffrn_reflns_theta_min         1.979
_diffrn_ambient_temperature      186.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2555
_reflns_number_total             3231
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         1.510
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.276
_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)+(0.0336P)²+47.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C2, C4, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
In1 In 0.250000 0.30271(2) 0.250000 0.01529(11) Uani 1 2 d S T P . .
In2 In 0.250000 0.250000 0.000000 0.01494(11) Uani 1 2 d S . P . .
O5 O 0.27972(13) 0.24244(11) 0.14595(18) 0.0244(6) Uani 1 1 d . . . . .
O4 O 0.34071(12) 0.30983(12) 0.3143(2) 0.0296(6) Uani 1 1 d . . . . .
O1 O 0.24304(15) 0.34349(12) 0.49627(19) 0.0352(7) Uani 1 1 d . . . . .
O2 O 0.22147(14) 0.37329(11) 0.34297(19) 0.0305(6) Uani 1 1 d . . . . .
O3 O 0.34330(12) 0.25464(14) 0.4506(2) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.23073(18) 0.38157(16) 0.4337(3) 0.0255(8) Uani 1 1 d . . . . .
C5 C 0.36826(17) 0.28332(17) 0.3823(3) 0.0265(8) Uani 1 1 d . . . . .
C6 C 0.43664(18) 0.28477(19) 0.3818(3) 0.0311(9) Uani 1 1 d . . . . .
C2 C 0.2279(2) 0.44272(17) 0.4688(3) 0.0322(9) Uani 1 1 d . U . . .
C8 C 0.4686(2) 0.2611(3) 0.4602(4) 0.0581(16) Uani 1 1 d . . . . .
H8 H 0.447079 0.244718 0.514391 0.070 Uiso 1 1 calc R U . . .
C7 C 0.4686(2) 0.3080(3) 0.3035(4) 0.0579(16) Uani 1 1 d . . . . .
H7 H 0.447074 0.324227 0.249088 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2315(4) 0.4859(2) 0.4062(4) 0.0888(19) Uani 1 1 d . U . . .
H4 H 0.233873 0.477691 0.337339 0.107 Uiso 1 1 calc R U . . .
C3 C 0.2320(4) 0.4571(3) 0.5630(4) 0.0950(19) Uani 1 1 d . U . . .
H3 H 0.235461 0.427351 0.611229 0.114 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 O5 2.083(2) 7_545 ?
In1 O5 2.083(2) . ?
In1 O4 2.172(3) 7_545 ?
In1 O4 2.172(3) . ?
In1 O2 2.152(3) . ?
In1 O2 2.152(3) 7_545 ?
In2 O5 2.082(2) . ?
In2 O5 2.082(2) 13 ?
In2 O1 2.168(3) 11_565 ?
In2 O1 2.168(3) 7_545 ?
In2 O3 2.150(3) 7_545 ?
In2 O3 2.150(3) 11_565 ?
O4 C5 1.258(4) . ?
O1 C1 1.249(5) . ?
O2 C1 1.257(4) . ?
O3 C5 1.261(5) . ?
C1 C2 1.493(5) . ?
C5 C6 1.496(5) . ?
C6 C8 1.381(6) . ?
C6 C7 1.377(6) . ?
C2 C4 1.310(7) . ?
C2 C3 1.317(7) . ?
C8 C8 1.371(9) 12_655 ?
C8 H8 0.9500 . ?
C7 C7 1.373(9) 12_655 ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.384(8) 4_566 ?
C3 H3 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
O5 In1 O5 95.99(14) 7_545 . ?
O5 In1 O4 92.02(11) . . ?
O5 In1 O4 92.02(11) 7_545 7_545 ?
O5 In1 O4 93.80(10) 7_545 . ?
O5 In1 O4 93.80(10) . 7_545 ?
O5 In1 O2 91.36(10) 7_545 . ?
O5 In1 O2 172.57(10) 7_545 7_545 ?
O5 In1 O2 91.36(10) . 7_545 ?
O5 In1 O2 172.57(10) . . ?
O4 In1 O4 171.30(15) . 7_545 ?
O2 In1 O4 84.88(10) . 7_545 ?
O2 In1 O4 88.52(11) . . ?
O2 In1 O4 88.53(11) 7_545 7_545 ?
O2 In1 O4 84.87(10) 7_545 . ?
O2 In1 O2 81.31(15) . 7_545 ?
O5 In2 O5 180.0 13 . ?
O5 In2 O1 87.72(10) 13 7_545 ?
O5 In2 O1 92.28(10) . 7_545 ?
O5 In2 O1 92.28(10) 13 11_565 ?
O5 In2 O1 87.72(10) . 11_565 ?
O5 In2 O3 89.60(11) . 11_565 ?
O5 In2 O3 90.40(11) . 7_545 ?
O5 In2 O3 89.61(11) 13 7_545 ?
O5 In2 O3 90.39(11) 13 11_565 ?
O1 In2 O1 180.0 7_545 11_565 ?
O3 In2 O1 89.44(12) 11_565 7_545 ?
O3 In2 O1 89.44(12) 7_545 11_565 ?
O3 In2 O1 90.56(12) 7_545 7_545 ?
O3 In2 O1 90.56(12) 11_565 11_565 ?
O3 In2 O3 180.00(4) 11_565 7_545 ?
In2 O5 In1 118.99(12) . . ?
C5 O4 In1 133.8(3) . . ?
C1 O1 In2 137.2(2) . 7_545 ?
C1 O2 In1 129.6(2) . . ?
C5 O3 In2 131.6(3) . 7_545 ?
O1 C1 O2 125.9(3) . . ?
O1 C1 C2 117.6(3) . . ?
O2 C1 C2 116.5(3) . . ?
O4 C5 O3 125.7(4) . . ?
O4 C5 C6 117.7(3) . . ?
O3 C5 C6 116.6(3) . . ?
C8 C6 C5 119.7(4) . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 C8 119.0(4) . . ?
C4 C2 C1 121.0(4) . . ?
C4 C2 C3 115.3(5) . . ?
C3 C2 C1 122.8(4) . . ?
C6 C8 H8 119.8 . . ?
C8 C8 C6 120.4(2) 12_655 . ?
C8 C8 H8 119.8 12_655 . ?
C6 C7 H7 119.7 . . ?
C7 C7 C6 120.5(2) 12_655 . ?
C7 C7 H7 119.7 12_655 . ?
C2 C4 H4 118.9 . . ?
C2 C4 C3 122.2(5) . 4_566 ?
C3 C4 H4 118.9 4_566 . ?
C2 C3 C4 122.0(5) . 4_566 ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 4_566 . ?

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
In1 O4 C5 O3 -21.1(6) . . . . ?
In1 O4 C5 C6 157.8(3) . . . . ?
In1 O2 C1 O1 -22.4(6) . . . . ?
In1 O2 C1 C2 156.3(3) . . . . ?
In2 O1 C1 O2 -5.1(7) 7_545 . . . ?
In2 O1 C1 C2 176.3(3) 7_545 . . . ?
In2 O3 C5 O4 -13.0(6) 7_545 . . . ?
In2 O3 C5 C6 168.1(3) 7_545 . . . ?
O4 C5 C6 C8 173.7(5) . . . . ?
O4 C5 C6 C7 -7.9(7) . . . . ?
O1 C1 C2 C4 161.7(6) . . . . ?
O1 C1 C2 C3 -6.6(8) . . . . ?
O2 C1 C2 C4 -17.0(8) . . . . ?
O2 C1 C2 C3 174.6(6) . . . . ?
O3 C5 C6 C8 -7.3(7) . . . . ?
O3 C5 C6 C7 171.1(5) . . . . ?
C1 C2 C4 C3 -176.8(7) . . . 4_566 ?
C1 C2 C3 C4 177.6(7) . . . 4_566 ?
C5 C6 C8 C8 178.8(3) . . . 12_655 ?
C5 C6 C7 C7 -178.8(3) . . . 12_655 ?
C8 C6 C7 C7 -0.4(6) . . . 12_655 ?
C7 C6 C8 C8 0.4(6) . . . 12_655 ?
C4 C2 C3 C4 8.7(11) . . . 4_566 ?
C3 C2 C4 C3 -7.6(10) . . . 4_566 ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.008 0.000 -0.012 2080 374 ' '
2 -0.008 0.500 -0.053 2062 374 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
