# 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 2020

####################################################################### 
# 
# 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_lxy190628
_database_code_depnum_ccdc_archive 'CCDC 2017666'
loop_
_audit_author_name
_audit_author_address
SN
;NingXia University
China
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_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         'C11 H7 In N2 O5, 1.25(H O0.5)'
_chemical_formula_sum            'C11 H8.25 In N2 O5.62'
_chemical_formula_weight         373.27
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   19.6248(12)
_cell_length_b                   7.2937(6)
_cell_length_c                   16.2808(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.445(6)
_cell_angle_gamma                90
_cell_volume                     2323.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.1430
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1458
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6006
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.500
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2233
_reflns_number_total             2760
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.715
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0753
_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. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: O7(0.125) H7(0.25)
4.a Riding coordinates:
 O5(H5), O7(H7)
4.b Free rotating group:
 O6(H6A)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11)
;
_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 0.75955(2) 0.60905(4) 0.76669(2) 0.00805(10) Uani 1 1 d . . . . .
O1 O 0.68710(12) 0.5880(4) 0.65949(17) 0.0145(7) Uani 1 1 d . . . . .
O2 O 0.59282(13) 0.7017(5) 0.71035(17) 0.0190(7) Uani 1 1 d . . . . .
O3 O 0.69927(12) 0.5136(4) 0.35891(16) 0.0115(6) Uani 1 1 d . . . . .
O4 O 0.65656(12) 0.7692(4) 0.29678(16) 0.0124(6) Uani 1 1 d . . . . .
O5 O 0.71061(12) 0.8604(4) 0.78458(17) 0.0119(6) Uani 1 1 d . . . . .
H5 H 0.668879 0.832897 0.770974 0.018 Uiso 1 1 d R . . . .
N1 N 0.43235(14) 0.8090(5) 0.44821(19) 0.0070(7) Uani 1 1 d . . . . .
N2 N 0.33624(15) 0.8683(5) 0.3753(2) 0.0109(8) Uani 1 1 d . . . . .
C1 C 0.59543(18) 0.6670(6) 0.5652(2) 0.0089(8) Uani 1 1 d . . . . .
C2 C 0.63563(18) 0.6338(6) 0.5005(2) 0.0091(8) Uani 1 1 d . . . . .
H2 H 0.680089 0.583733 0.511486 0.011 Uiso 1 1 calc R . . . .
C3 C 0.61200(17) 0.6725(6) 0.4206(2) 0.0079(8) Uani 1 1 d . . . . .
C4 C 0.54619(18) 0.7401(6) 0.4030(2) 0.0111(9) Uani 1 1 d . . . . .
H4 H 0.530652 0.774890 0.348456 0.013 Uiso 1 1 calc R . . . .
C5 C 0.50345(17) 0.7556(5) 0.4676(2) 0.0087(8) Uani 1 1 d . . . . .
C6 C 0.52774(18) 0.7244(6) 0.5481(3) 0.0112(9) Uani 1 1 d . . . . .
H6 H 0.498784 0.741712 0.591561 0.013 Uiso 1 1 calc R . . . .
C7 C 0.62600(18) 0.6493(6) 0.6522(2) 0.0111(9) Uani 1 1 d . . . . .
C8 C 0.65924(17) 0.6510(6) 0.3525(2) 0.0079(8) Uani 1 1 d . U . . .
C9 C 0.40131(18) 0.8218(6) 0.3726(2) 0.0132(9) Uani 1 1 d . . . . .
H9 H 0.422981 0.800402 0.323276 0.016 Uiso 1 1 calc R . . . .
C10 C 0.38529(19) 0.8485(6) 0.5041(3) 0.0143(9) Uani 1 1 d . . . . .
H10 H 0.392632 0.849983 0.562466 0.017 Uiso 1 1 calc R . . . .
C11 C 0.32625(18) 0.8849(6) 0.4582(2) 0.0131(9) Uani 1 1 d . . . . .
H11 H 0.284230 0.916997 0.479732 0.016 Uiso 1 1 calc R . . . .
O6 O 0.500000 0.9694(7) 0.750000 0.0256(11) Uani 1 2 d S T P . .
H6A H 0.533532 0.902369 0.739036 0.038 Uiso 1 1 d G . . . .
O7 O 0.500000 0.547(3) 0.250000 0.046(6) Uani 0.25 2 d S T P . .
H7 H 0.531940 0.476463 0.237310 0.068 Uiso 0.25 1 d R . . . .


_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 2.169(3) . ?
In1 O3 2.175(3) 6_566 ?
In1 O4 2.198(3) 7_666 ?
In1 O5 2.098(3) 4_646 ?
In1 O5 2.101(3) . ?
In1 N2 2.238(3) 8_566 ?
O1 C7 1.277(4) . ?
O2 C7 1.250(5) . ?
O3 C8 1.273(5) . ?
O4 C8 1.249(5) . ?
O5 H5 0.8556 . ?
N1 C5 1.459(4) . ?
N1 C9 1.334(5) . ?
N1 C10 1.376(5) . ?
N2 C9 1.325(5) . ?
N2 C11 1.384(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.400(5) . ?
C1 C7 1.499(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(5) . ?
C3 C4 1.391(5) . ?
C3 C8 1.507(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(5) . ?
C5 C6 1.378(6) . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.356(5) . ?
C11 H11 0.9500 . ?
O6 H6A 0.8499 . ?
O6 H6A 0.85(5) 2_656 ?
O7 H7 0.8501 . ?
O7 H7 0.8500 2_655 ?

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 O3 99.71(10) . 6_566 ?
O1 In1 O4 96.80(10) . 7_666 ?
O1 In1 N2 178.67(10) . 8_566 ?
O3 In1 O4 163.38(10) 6_566 7_666 ?
O3 In1 N2 81.56(10) 6_566 8_566 ?
O4 In1 N2 81.92(11) 7_666 8_566 ?
O5 In1 O1 83.98(11) . . ?
O5 In1 O1 78.73(10) 4_646 . ?
O5 In1 O3 89.10(10) . 6_566 ?
O5 In1 O3 95.89(10) 4_646 6_566 ?
O5 In1 O4 94.57(10) . 7_666 ?
O5 In1 O4 85.41(10) 4_646 7_666 ?
O5 In1 O5 162.571(18) 4_646 . ?
O5 In1 N2 96.47(12) . 8_566 ?
O5 In1 N2 100.77(11) 4_646 8_566 ?
C7 O1 In1 127.1(2) . . ?
C8 O3 In1 129.2(2) . 6_565 ?
C8 O4 In1 129.0(2) . 7_666 ?
In1 O5 In1 123.67(12) 4_656 . ?
In1 O5 H5 101.4 . . ?
In1 O5 H5 113.0 4_656 . ?
C9 N1 C5 125.3(3) . . ?
C9 N1 C10 108.3(3) . . ?
C10 N1 C5 126.3(3) . . ?
C9 N2 In1 125.7(3) . 8_465 ?
C9 N2 C11 105.4(3) . . ?
C11 N2 In1 128.8(2) . 8_465 ?
C2 C1 C6 119.2(4) . . ?
C2 C1 C7 119.5(3) . . ?
C6 C1 C7 121.2(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 C8 119.5(3) . . ?
C4 C3 C8 119.9(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.3(4) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 N1 118.5(3) . . ?
C6 C5 N1 120.2(3) . . ?
C6 C5 C4 121.2(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
O1 C7 C1 115.0(3) . . ?
O2 C7 O1 125.2(4) . . ?
O2 C7 C1 119.7(3) . . ?
O3 C8 C3 115.6(3) . . ?
O4 C8 O3 126.4(3) . . ?
O4 C8 C3 117.9(3) . . ?
N1 C9 H9 124.5 . . ?
N2 C9 N1 111.0(3) . . ?
N2 C9 H9 124.5 . . ?
N1 C10 H10 127.3 . . ?
C11 C10 N1 105.4(4) . . ?
C11 C10 H10 127.3 . . ?
N2 C11 H11 125.0 . . ?
C10 C11 N2 109.9(3) . . ?
C10 C11 H11 125.0 . . ?
H6A O6 H6A 109.7 . 2_656 ?
H7 O7 H7 105.1 . 2_655 ?

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
_geom_hbond_publ_flag
O5 H5 O2 0.86 1.97 2.777(4) 156.3 . yes
O6 H6A O2 0.85 1.95 2.781(5) 165.7 . yes
O7 H7 O2 0.85 1.84 2.686(16) 172.4 6_565 yes

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 O1 C7 O2 -14.4(6) . . . . ?
In1 O1 C7 C1 162.0(3) . . . . ?
In1 O3 C8 O4 -16.2(6) 6_565 . . . ?
In1 O3 C8 C3 165.3(2) 6_565 . . . ?
In1 O4 C8 O3 -37.4(6) 7_666 . . . ?
In1 O4 C8 C3 141.1(3) 7_666 . . . ?
In1 N2 C9 N1 -175.9(3) 8_465 . . . ?
In1 N2 C11 C10 175.6(3) 8_465 . . . ?
N1 C5 C6 C1 177.8(4) . . . . ?
N1 C10 C11 N2 0.0(5) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C1 C2 C3 C8 174.5(4) . . . . ?
C2 C1 C6 C5 -3.2(6) . . . . ?
C2 C1 C7 O1 -5.8(6) . . . . ?
C2 C1 C7 O2 170.8(4) . . . . ?
C2 C3 C4 C5 -4.3(6) . . . . ?
C2 C3 C8 O3 38.7(5) . . . . ?
C2 C3 C8 O4 -140.0(4) . . . . ?
C3 C4 C5 N1 -174.0(4) . . . . ?
C3 C4 C5 C6 7.1(6) . . . . ?
C4 C3 C8 O3 -144.7(4) . . . . ?
C4 C3 C8 O4 36.7(6) . . . . ?
C4 C5 C6 C1 -3.3(6) . . . . ?
C5 N1 C9 N2 178.2(4) . . . . ?
C5 N1 C10 C11 -178.1(4) . . . . ?
C6 C1 C2 C3 6.0(6) . . . . ?
C6 C1 C7 O1 177.0(4) . . . . ?
C6 C1 C7 O2 -6.4(6) . . . . ?
C7 C1 C2 C3 -171.2(4) . . . . ?
C7 C1 C6 C5 173.9(4) . . . . ?
C8 C3 C4 C5 179.1(4) . . . . ?
C9 N1 C5 C4 9.3(6) . . . . ?
C9 N1 C5 C6 -171.7(4) . . . . ?
C9 N1 C10 C11 -0.1(5) . . . . ?
C9 N2 C11 C10 0.1(5) . . . . ?
C10 N1 C5 C4 -173.0(4) . . . . ?
C10 N1 C5 C6 5.9(6) . . . . ?
C10 N1 C9 N2 0.2(5) . . . . ?
C11 N2 C9 N1 -0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
