# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 2077713'
loop_
_audit_author_name
_audit_author_address
'Xiuli guo'
;Jilin university
China
;
_audit_update_record             
;
2021-09-18 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Cl In N O7'
_chemical_formula_weight         457.52

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.8240(7)
_cell_length_b                   13.4404(5)
_cell_length_c                   13.6238(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.2910(10)
_cell_angle_gamma                90
_cell_volume                     3165.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    199(2)
_cell_measurement_reflns_used    3781
_cell_measurement_theta_min      4.314
_cell_measurement_theta_max      28.363

_exptl_crystal_description       rob
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.699
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      199(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10135
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.314
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             3781
_reflns_number_gt                3700
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0060P)²+9.3933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3781
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0487
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.17952(2) 0.35541(2) 0.28470(2) 0.01556(5) Uani 1 1 d . . . . .
Cl1 Cl 0.21600(3) 0.31946(4) 0.14184(4) 0.02925(11) Uani 1 1 d . . . . .
O1 O 0.02381(8) 0.84738(9) 0.15234(12) 0.0206(3) Uani 1 1 d . . . . .
O1W O 0.74257(15) 0.03481(15) 0.08571(17) 0.0646(7) Uani 1 1 d G . . . .
H1WA H 0.7375 -0.0222 0.1116 0.097 Uiso 1 1 d G U . . .
H1WB H 0.7735 0.0687 0.1454 0.097 Uiso 1 1 d G U . . .
O2 O -0.19949(7) 1.18926(10) -0.06729(11) 0.0188(3) Uani 1 1 d . . . . .
O3 O -0.22459(8) 1.03518(10) -0.12618(12) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.15798(7) 1.17932(10) 0.28776(11) 0.0208(3) Uani 1 1 d . . . . .
O5 O 0.06732(8) 1.28421(10) 0.18169(12) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.10719(9) 0.49740(11) 0.21376(13) 0.0189(3) Uani 1 1 d . . . . .
C1 C -0.00359(10) 0.94227(12) 0.12389(14) 0.0140(3) Uani 1 1 d . . . . .
C2 C -0.07934(10) 0.96768(12) 0.04667(14) 0.0149(3) Uani 1 1 d . . . . .
H2 H -0.1173 0.9177 0.0091 0.018 Uiso 1 1 calc R U . . .
C3 C -0.09852(9) 1.06892(12) 0.02540(14) 0.0143(3) Uani 1 1 d . . . . .
C4 C -0.04379(10) 1.14186(12) 0.08015(14) 0.0148(3) Uani 1 1 d . . . . .
H4 H -0.0576 1.2101 0.0653 0.018 Uiso 1 1 calc R U . . .
C5 C 0.03202(9) 1.11487(12) 0.15763(14) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.05222(10) 1.01552(13) 0.17951(14) 0.0147(3) Uani 1 1 d . . . . .
H6 H 0.1038 0.9973 0.2321 0.018 Uiso 1 1 calc R U . . .
C7 C -0.17814(10) 1.09934(13) -0.05970(15) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.08955(10) 1.19564(13) 0.21339(14) 0.0157(3) Uani 1 1 d . . . . .
C9 C -0.02731(10) 0.76655(13) 0.09838(15) 0.0175(3) Uani 1 1 d . . . . .
H9A H -0.0518 0.7733 0.0156 0.021 Uiso 1 1 calc R U . . .
H9B H -0.0685 0.7650 0.1194 0.021 Uiso 1 1 calc R U . . .
C10 C 0.02930(11) 0.49503(14) 0.15170(17) 0.0226(4) Uani 1 1 d . . . . .
H10 H 0.0040 0.4323 0.1344 0.027 Uiso 1 1 calc R U . . .
C11 C -0.01516(11) 0.58019(14) 0.11221(17) 0.0222(4) Uani 1 1 d . . . . .
H11 H -0.0698 0.5753 0.0683 0.027 Uiso 1 1 calc R U . . .
C12 C 0.02038(10) 0.67302(13) 0.13694(15) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.10029(11) 0.67538(14) 0.19875(19) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.1269 0.7372 0.2162 0.033 Uiso 1 1 calc R U . . .
C14 C 0.14110(11) 0.58730(15) 0.2350(2) 0.0289(4) Uani 1 1 d . . . . .
H14 H 0.1959 0.5905 0.2771 0.035 Uiso 1 1 calc R U . . .
O6 O 0.15113(8) 0.35481(10) 0.42163(12) 0.0233(3) Uani 1 1 d . . . . .
H6A H 0.1787 0.3997 0.4714 0.035 Uiso 1 1 d R U . . .
H6B H 0.1659 0.2986 0.4581 0.035 Uiso 1 1 d 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 2.1860(13) 1_545 ?
In1 O6 2.1964(14) . ?
In1 O3 2.2342(13) 8_566 ?
In1 N1 2.2970(15) . ?
In1 O2 2.3339(13) 8_566 ?
In1 O4 2.4090(14) 1_545 ?
In1 Cl1 2.4335(5) . ?
In1 C7 2.6406(17) 8_566 ?
In1 C8 2.6535(17) 1_545 ?
O1 C1 1.3659(19) . ?
O1 C9 1.421(2) . ?
O1W H1WA 0.8699 . ?
O1W H1WB 0.8700 . ?
O2 C7 1.268(2) . ?
O2 In1 2.3339(13) 8_465 ?
O3 C7 1.263(2) . ?
O3 In1 2.2342(13) 8_465 ?
O4 C8 1.253(2) . ?
O4 In1 2.4089(13) 1_565 ?
O5 C8 1.269(2) . ?
O5 In1 2.1859(13) 1_565 ?
N1 C14 1.344(2) . ?
N1 C10 1.350(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.395(2) . ?
C2 C3 1.404(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C3 C7 1.487(2) . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 C8 1.486(2) . ?
C6 H6 0.9500 . ?
C7 In1 2.6407(17) 8_465 ?
C8 In1 2.6535(17) 1_565 ?
C9 C12 1.505(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O6 H6A 0.8720 . ?
O6 H6B 0.8720 . ?

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 O6 86.59(6) 1_545 . ?
O5 In1 O3 164.80(5) 1_545 8_566 ?
O6 In1 O3 92.54(6) . 8_566 ?
O5 In1 N1 82.18(5) 1_545 . ?
O6 In1 N1 89.65(6) . . ?
O3 In1 N1 82.64(5) 8_566 . ?
O5 In1 O2 137.29(5) 1_545 8_566 ?
O6 In1 O2 81.22(5) . 8_566 ?
O3 In1 O2 57.20(5) 8_566 8_566 ?
N1 In1 O2 138.02(5) . 8_566 ?
O5 In1 O4 56.48(5) 1_545 1_545 ?
O6 In1 O4 81.98(5) . 1_545 ?
O3 In1 O4 138.43(5) 8_566 1_545 ?
N1 In1 O4 138.08(5) . 1_545 ?
O2 In1 O4 81.27(4) 8_566 1_545 ?
O5 In1 Cl1 90.39(4) 1_545 . ?
O6 In1 Cl1 168.09(4) . . ?
O3 In1 Cl1 93.36(4) 8_566 . ?
N1 In1 Cl1 101.36(4) . . ?
O2 In1 Cl1 93.33(4) 8_566 . ?
O4 In1 Cl1 86.75(4) 1_545 . ?
O5 In1 C7 165.53(5) 1_545 8_566 ?
O6 In1 C7 86.34(5) . 8_566 ?
O3 In1 C7 28.51(5) 8_566 8_566 ?
N1 In1 C7 110.39(5) . 8_566 ?
O2 In1 C7 28.69(5) 8_566 8_566 ?
O4 In1 C7 109.95(5) 1_545 8_566 ?
Cl1 In1 C7 93.95(4) . 8_566 ?
O5 In1 C8 28.37(5) 1_545 1_545 ?
O6 In1 C8 84.40(5) . 1_545 ?
O3 In1 C8 166.51(5) 8_566 1_545 ?
N1 In1 C8 110.42(6) . 1_545 ?
O2 In1 C8 109.31(5) 8_566 1_545 ?
O4 In1 C8 28.13(5) 1_545 1_545 ?
Cl1 In1 C8 87.48(4) . 1_545 ?
C7 In1 C8 138.00(5) 8_566 1_545 ?
C1 O1 C9 118.90(13) . . ?
H1WA O1W H1WB 104.5 . . ?
C7 O2 In1 89.21(10) . 8_465 ?
C7 O3 In1 93.92(11) . 8_465 ?
C8 O4 In1 86.84(10) . 1_565 ?
C8 O5 In1 96.74(10) . 1_565 ?
C14 N1 C10 117.04(16) . . ?
C14 N1 In1 120.86(12) . . ?
C10 N1 In1 122.09(12) . . ?
O1 C1 C2 125.20(15) . . ?
O1 C1 C6 113.90(14) . . ?
C2 C1 C6 120.90(15) . . ?
C1 C2 C3 118.51(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.00(15) . . ?
C4 C3 C7 118.70(15) . . ?
C2 C3 C7 120.28(15) . . ?
C3 C4 C5 119.66(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.27(15) . . ?
C6 C5 C8 121.73(15) . . ?
C4 C5 C8 117.99(15) . . ?
C5 C6 C1 119.66(15) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O3 C7 O2 119.67(15) . . ?
O3 C7 C3 119.64(16) . . ?
O2 C7 C3 120.68(15) . . ?
O3 C7 In1 57.58(9) . 8_465 ?
O2 C7 In1 62.10(9) . 8_465 ?
C3 C7 In1 177.18(13) . 8_465 ?
O4 C8 O5 119.84(16) . . ?
O4 C8 C5 122.82(16) . . ?
O5 C8 C5 117.34(15) . . ?
O4 C8 In1 65.02(9) . 1_565 ?
O5 C8 In1 54.90(9) . 1_565 ?
C5 C8 In1 171.34(12) . 1_565 ?
O1 C9 C12 106.91(14) . . ?
O1 C9 H9A 110.3 . . ?
C12 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C12 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N1 C10 C11 122.69(17) . . ?
N1 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 119.82(17) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 117.48(17) . . ?
C13 C12 C9 122.02(16) . . ?
C11 C12 C9 120.50(16) . . ?
C14 C13 C12 119.59(18) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N1 C14 C13 123.35(18) . . ?
N1 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
In1 O6 H6A 109.5 . . ?
In1 O6 H6B 109.5 . . ?
H6A O6 H6B 104.4 . . ?

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
C9 O1 C1 C2 1.5(3) . . . . ?
C9 O1 C1 C6 -178.08(16) . . . . ?
O1 C1 C2 C3 -179.30(16) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C7 177.70(16) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C7 C3 C4 C5 -177.83(16) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C8 179.00(16) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C8 C5 C6 C1 -179.10(16) . . . . ?
O1 C1 C6 C5 179.59(16) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
In1 O3 C7 O2 -0.52(19) 8_465 . . . ?
In1 O3 C7 C3 -179.49(14) 8_465 . . . ?
In1 O2 C7 O3 0.50(18) 8_465 . . . ?
In1 O2 C7 C3 179.46(15) 8_465 . . . ?
C4 C3 C7 O3 166.07(17) . . . . ?
C2 C3 C7 O3 -12.1(3) . . . . ?
C4 C3 C7 O2 -12.9(3) . . . . ?
C2 C3 C7 O2 168.97(17) . . . . ?
In1 O4 C8 O5 -3.13(17) 1_565 . . . ?
In1 O4 C8 C5 175.78(16) 1_565 . . . ?
In1 O5 C8 O4 3.47(19) 1_565 . . . ?
In1 O5 C8 C5 -175.50(13) 1_565 . . . ?
C6 C5 C8 O4 -4.3(3) . . . . ?
C4 C5 C8 O4 176.63(17) . . . . ?
C6 C5 C8 O5 174.59(17) . . . . ?
C4 C5 C8 O5 -4.4(2) . . . . ?
C1 O1 C9 C12 174.11(15) . . . . ?
C14 N1 C10 C11 -1.1(3) . . . . ?
In1 N1 C10 C11 177.38(15) . . . . ?
N1 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C10 C11 C12 C9 -177.67(19) . . . . ?
O1 C9 C12 C13 -9.1(3) . . . . ?
O1 C9 C12 C11 170.14(17) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C9 C12 C13 C14 178.0(2) . . . . ?
C10 N1 C14 C13 1.4(3) . . . . ?
In1 N1 C14 C13 -177.05(18) . . . . ?
C12 C13 C14 N1 -0.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA Cl1 0.87 2.25 3.104(2) 168.0 3_545
O1W H1WB O4 0.87 1.92 2.703(2) 149.5 2_645
C10 H10 O5 0.95 2.27 2.909(2) 123.8 1_545
C13 H13 Cl1 0.95 2.96 3.740(2) 140.2 4
C14 H14 O3 0.95 2.24 2.907(2) 126.0 8_566
O6 H6A O1W 0.87 1.69 2.553(2) 167.5 8_456
O6 H6B O2 0.87 1.96 2.8189(19) 167.4 2_545

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_sad_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2077712'
loop_
_audit_author_name
_audit_author_address
'Xiuli guo'
;Jilin university
China
;
_audit_update_record             
;
2021-09-18 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 In N2 O9'
_chemical_formula_weight         466.07

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.849(2)
_cell_length_b                   13.4206(15)
_cell_length_c                   13.6014(15)
_cell_angle_alpha                90
_cell_angle_beta                 119.380(2)
_cell_angle_gamma                90
_cell_volume                     3157.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2826
_cell_measurement_theta_min      2.355
_cell_measurement_theta_max      25.190

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.553
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23426
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2826
_reflns_number_gt                2481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+133.0363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     227
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.18685(3) 0.36674(5) 0.30036(6) 0.0265(2) Uani 1 1 d . . . . .
O1 O 0.0389(4) 0.8601(5) 0.1663(6) 0.0324(17) Uani 1 1 d . . . . .
O2 O -0.1930(3) 1.1907(5) -0.0641(6) 0.0284(16) Uani 1 1 d . . . . .
O3 O -0.2133(4) 1.0334(5) -0.1069(6) 0.0353(18) Uani 1 1 d . . . . .
O4 O 0.1641(4) 1.1966(5) 0.3001(6) 0.0379(19) Uani 1 1 d . . . . .
O5 O 0.0768(4) 1.2984(5) 0.1823(7) 0.048(2) Uani 1 1 d . . . . .
O6 O 0.1603(4) 0.3677(6) 0.4405(7) 0.0433(19) Uani 1 1 d . . . . .
H6A H 0.1725 0.3117 0.4739 0.065 Uiso 1 1 d R U . . .
H6B H 0.1897 0.4093 0.4902 0.065 Uiso 1 1 d R U . . .
N1 N 0.1181(4) 0.5087(6) 0.2376(7) 0.030(2) Uani 1 1 d . . . . .
C1 C 0.0102(5) 0.9553(7) 0.1365(8) 0.022(2) Uani 1 1 d . . . . .
C2 C -0.0655(5) 0.9771(6) 0.0596(8) 0.0209(19) Uani 1 1 d . . . . .
H2 H -0.1012 0.9263 0.0241 0.025 Uiso 1 1 calc R U . . .
C3 C -0.0877(5) 1.0768(7) 0.0360(7) 0.0216(19) Uani 1 1 d . . . . .
C4 C -0.0349(5) 1.1532(6) 0.0893(7) 0.0206(19) Uani 1 1 d . . . . .
H4 H -0.0502 1.2195 0.0742 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0411(5) 1.1286(7) 0.1657(8) 0.0224(19) Uani 1 1 d . . . . .
C6 C 0.0637(5) 1.0308(7) 0.1903(7) 0.0202(19) Uani 1 1 d . . . . .
H6 H 0.1145 1.0153 0.2427 0.024 Uiso 1 1 calc R U . . .
C7 C -0.1687(5) 1.1033(7) -0.0479(8) 0.023(2) Uani 1 1 d . . . . .
C8 C 0.0974(5) 1.2110(7) 0.2202(8) 0.025(2) Uani 1 1 d . . . . .
C9 C -0.0114(5) 0.7784(6) 0.1133(8) 0.0245(15) Uani 1 1 d . . . . .
H9A H -0.0342 0.7833 0.0320 0.029 Uiso 1 1 calc R U . . .
H9B H -0.0528 0.7780 0.1319 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0425(6) 0.5092(7) 0.1635(10) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.0173 0.4483 0.1391 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0000(6) 0.5946(8) 0.1215(10) 0.042(3) Uani 1 1 d . . . . .
H11 H -0.0527 0.5913 0.0705 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0360(5) 0.6843(6) 0.1556(8) 0.0245(15) Uani 1 1 d . . . . .
C13 C 0.1131(6) 0.6865(7) 0.2302(11) 0.043(3) Uani 1 1 d . . . . .
H13 H 0.1391 0.7469 0.2542 0.051 Uiso 1 1 calc R U . . .
C14 C 0.1523(6) 0.5971(8) 0.2699(11) 0.049(4) Uani 1 1 d . . . . .
H14 H 0.2049 0.5991 0.3216 0.059 Uiso 1 1 calc R U . . .
N2 N 0.2262(9) 0.3943(15) 0.1115(12) 0.096(6) Uani 1 1 d . . . . .
O7 O 0.2285(6) 0.3371(8) 0.1824(8) 0.065(3) Uani 1 1 d . . . . .
O8 O 0.1895(9) 0.4724(12) 0.0947(12) 0.107(3) Uani 1 1 d . U . . .
O9 O 0.2707(17) 0.384(2) 0.066(2) 0.107(3) Uani 0.5 1 d . U P A 1
O9' O 0.2075(18) 0.341(2) 0.021(3) 0.107(3) Uani 0.5 1 d . U P A 2


_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 O7 2.171(10) . ?
In1 O5 2.179(7) 1_545 ?
In1 O3 2.205(6) 8_566 ?
In1 O6 2.212(8) . ?
In1 N1 2.254(7) . ?
In1 O2 2.317(6) 8_566 ?
In1 O4 2.327(7) 1_545 ?
In1 C8 2.610(9) 1_545 ?
In1 C7 2.614(8) 8_566 ?
O1 C1 1.376(11) . ?
O1 C9 1.419(11) . ?
O2 C7 1.246(11) . ?
O2 In1 2.317(6) 8_465 ?
O3 C7 1.269(11) . ?
O3 In1 2.205(6) 8_465 ?
O4 C8 1.249(11) . ?
O4 In1 2.327(7) 1_565 ?
O5 C8 1.266(12) . ?
O5 In1 2.179(7) 1_565 ?
O6 H6A 0.8500 . ?
O6 H6B 0.8500 . ?
N1 C14 1.329(13) . ?
N1 C10 1.336(12) . ?
C1 C2 1.376(12) . ?
C1 C6 1.388(12) . ?
C2 C3 1.396(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(12) . ?
C3 C7 1.488(11) . ?
C4 C5 1.389(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(13) . ?
C5 C8 1.486(12) . ?
C6 H6 0.9300 . ?
C7 In1 2.614(8) 8_465 ?
C8 In1 2.610(9) 1_565 ?
C9 C12 1.511(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.372(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(14) . ?
C13 C14 1.387(14) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N2 O7 1.216(19) . ?
N2 O8 1.23(2) . ?
N2 O9 1.31(3) . ?
N2 O9' 1.32(3) . ?

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
O7 In1 O5 89.2(4) . 1_545 ?
O7 In1 O3 88.5(4) . 8_566 ?
O5 In1 O3 166.4(3) 1_545 8_566 ?
O7 In1 O6 167.2(3) . . ?
O5 In1 O6 93.5(3) 1_545 . ?
O3 In1 O6 91.8(3) 8_566 . ?
O7 In1 N1 104.7(4) . . ?
O5 In1 N1 82.8(3) 1_545 . ?
O3 In1 N1 84.8(3) 8_566 . ?
O6 In1 N1 88.1(3) . . ?
O7 In1 O2 84.9(3) . 8_566 ?
O5 In1 O2 135.6(2) 1_545 8_566 ?
O3 In1 O2 57.4(2) 8_566 8_566 ?
O6 In1 O2 84.5(3) . 8_566 ?
N1 In1 O2 141.1(3) . 8_566 ?
O7 In1 O4 87.9(4) . 1_545 ?
O5 In1 O4 57.5(2) 1_545 1_545 ?
O3 In1 O4 135.8(2) 8_566 1_545 ?
O6 In1 O4 83.1(3) . 1_545 ?
N1 In1 O4 138.4(3) . 1_545 ?
O2 In1 O4 78.4(2) 8_566 1_545 ?
O7 In1 C8 88.4(4) . 1_545 ?
O5 In1 C8 28.9(3) 1_545 1_545 ?
O3 In1 C8 164.2(3) 8_566 1_545 ?
O6 In1 C8 87.9(3) . 1_545 ?
N1 In1 C8 110.9(3) . 1_545 ?
O2 In1 C8 106.8(2) 8_566 1_545 ?
O4 In1 C8 28.6(3) 1_545 1_545 ?
O7 In1 C7 86.8(4) . 8_566 ?
O5 In1 C7 163.9(3) 1_545 8_566 ?
O3 In1 C7 29.0(3) 8_566 8_566 ?
O6 In1 C7 87.2(3) . 8_566 ?
N1 In1 C7 113.2(3) . 8_566 ?
O2 In1 C7 28.5(3) 8_566 8_566 ?
O4 In1 C7 106.8(3) 1_545 8_566 ?
C8 In1 C7 135.3(3) 1_545 8_566 ?
C1 O1 C9 118.8(7) . . ?
C7 O2 In1 89.2(5) . 8_465 ?
C7 O3 In1 93.7(5) . 8_465 ?
C8 O4 In1 88.4(6) . 1_565 ?
C8 O5 In1 94.8(5) . 1_565 ?
In1 O6 H6A 109.3 . . ?
In1 O6 H6B 109.2 . . ?
H6A O6 H6B 104.5 . . ?
C14 N1 C10 116.6(8) . . ?
C14 N1 In1 120.9(6) . . ?
C10 N1 In1 122.5(6) . . ?
C2 C1 O1 124.1(8) . . ?
C2 C1 C6 120.9(8) . . ?
O1 C1 C6 115.0(7) . . ?
C1 C2 C3 118.8(8) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.0(8) . . ?
C4 C3 C7 118.6(8) . . ?
C2 C3 C7 120.4(8) . . ?
C5 C4 C3 118.7(8) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 120.9(8) . . ?
C6 C5 C8 120.9(8) . . ?
C4 C5 C8 118.1(8) . . ?
C5 C6 C1 119.7(8) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O2 C7 O3 119.6(8) . . ?
O2 C7 C3 122.6(8) . . ?
O3 C7 C3 117.7(8) . . ?
O2 C7 In1 62.4(4) . 8_465 ?
O3 C7 In1 57.3(4) . 8_465 ?
C3 C7 In1 175.0(7) . 8_465 ?
O4 C8 O5 119.3(8) . . ?
O4 C8 C5 122.4(8) . . ?
O5 C8 C5 118.3(8) . . ?
O4 C8 In1 63.0(5) . 1_565 ?
O5 C8 In1 56.3(5) . 1_565 ?
C5 C8 In1 174.5(7) . 1_565 ?
O1 C9 C12 107.5(7) . . ?
O1 C9 H9A 110.2 . . ?
C12 C9 H9A 110.2 . . ?
O1 C9 H9B 110.2 . . ?
C12 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N1 C10 C11 123.5(9) . . ?
N1 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C12 C11 C10 119.0(9) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 119.1(9) . . ?
C13 C12 C9 121.9(8) . . ?
C11 C12 C9 119.0(8) . . ?
C12 C13 C14 118.8(9) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N1 C14 C13 123.1(9) . . ?
N1 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
O7 N2 O8 118.2(15) . . ?
O7 N2 O9 122.4(19) . . ?
O8 N2 O9 118(2) . . ?
O7 N2 O9' 106(2) . . ?
O8 N2 O9' 115.0(19) . . ?
N2 O7 In1 126.2(10) . . ?

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
C9 O1 C1 C2 1.7(14) . . . . ?
C9 O1 C1 C6 -178.4(9) . . . . ?
O1 C1 C2 C3 -179.8(9) . . . . ?
C6 C1 C2 C3 0.3(15) . . . . ?
C1 C2 C3 C4 -0.5(14) . . . . ?
C1 C2 C3 C7 179.1(9) . . . . ?
C2 C3 C4 C5 1.1(14) . . . . ?
C7 C3 C4 C5 -178.6(9) . . . . ?
C3 C4 C5 C6 -1.5(14) . . . . ?
C3 C4 C5 C8 178.7(9) . . . . ?
C4 C5 C6 C1 1.3(15) . . . . ?
C8 C5 C6 C1 -178.9(9) . . . . ?
C2 C1 C6 C5 -0.7(15) . . . . ?
O1 C1 C6 C5 179.4(9) . . . . ?
In1 O2 C7 O3 2.2(10) 8_465 . . . ?
In1 O2 C7 C3 179.9(9) 8_465 . . . ?
In1 O3 C7 O2 -2.3(10) 8_465 . . . ?
In1 O3 C7 C3 179.9(8) 8_465 . . . ?
C4 C3 C7 O2 -7.2(15) . . . . ?
C2 C3 C7 O2 173.1(9) . . . . ?
C4 C3 C7 O3 170.5(9) . . . . ?
C2 C3 C7 O3 -9.1(14) . . . . ?
In1 O4 C8 O5 0.4(11) 1_565 . . . ?
In1 O4 C8 C5 178.9(9) 1_565 . . . ?
In1 O5 C8 O4 -0.4(11) 1_565 . . . ?
In1 O5 C8 C5 -179.0(8) 1_565 . . . ?
C6 C5 C8 O4 -9.2(16) . . . . ?
C4 C5 C8 O4 170.6(10) . . . . ?
C6 C5 C8 O5 169.3(10) . . . . ?
C4 C5 C8 O5 -10.8(15) . . . . ?
C1 O1 C9 C12 176.2(9) . . . . ?
C14 N1 C10 C11 -0.5(19) . . . . ?
In1 N1 C10 C11 -178.0(10) . . . . ?
N1 C10 C11 C12 1(2) . . . . ?
C10 C11 C12 C13 0.0(19) . . . . ?
C10 C11 C12 C9 -177.4(11) . . . . ?
O1 C9 C12 C13 -0.8(14) . . . . ?
O1 C9 C12 C11 176.6(10) . . . . ?
C11 C12 C13 C14 -0.6(19) . . . . ?
C9 C12 C13 C14 176.7(12) . . . . ?
C10 N1 C14 C13 0(2) . . . . ?
In1 N1 C14 C13 177.4(11) . . . . ?
C12 C13 C14 N1 1(2) . . . . ?
O8 N2 O7 In1 -9(2) . . . . ?
O9 N2 O7 In1 159.8(19) . . . . ?
O9' N2 O7 In1 -140.0(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O3 0.93 2.28 2.934(12) 127.0 8_566
C13 H13 O7 0.93 2.62 3.422(14) 144.2 4
C10 H10 O5 0.93 2.26 2.891(12) 124.7 1_545
O6 H6B O8 0.85 2.13 2.855(18) 142.7 6_566
O6 H6A O2 0.85 1.95 2.796(10) 171.0 2_545
O6 H6A O2 0.85 1.95 2.796(10) 171.0 2_545
O6 H6B O8 0.85 2.13 2.855(18) 142.7 6_566
C10 H10 O5 0.93 2.26 2.891(12) 124.7 1_545
C13 H13 O7 0.93 2.62 3.422(14) 144.2 4
C14 H14 O3 0.93 2.28 2.934(12) 127.0 8_566
O6 H6A O2 0.85 1.95 2.796(10) 171.0 2_545
O6 H6B O8 0.85 2.13 2.855(18) 142.7 6_566
C10 H10 O5 0.93 2.26 2.891(12) 124.7 1_545
C13 H13 O7 0.93 2.62 3.422(14) 144.2 4
C14 H14 O3 0.93 2.28 2.934(12) 127.0 8_566

_refine_diff_density_max         2.072
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.186

_shelxl_version_number           2014-3



