# 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 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1525687'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
_audit_creation_date             2017-02-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 Cl In O8, 3(H2 O), 2(C6 H6 N O2)'
_chemical_formula_sum            'C16 H18 Cl In N2 O15'
_chemical_formula_weight         628.59
_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'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.729(3)
_cell_length_b                   11.511(4)
_cell_length_c                   11.634(4)
_cell_angle_alpha                104.630(5)
_cell_angle_beta                 93.584(4)
_cell_angle_gamma                95.062(5)
_cell_volume                     1122.3(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6368
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.064
_cell_measurement_theta_min      2.352
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    1.253
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0615 before and 0.0195 after correction. The Ratio of minimum to maximum transmission is 0.8678. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6327
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.224
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_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                4306
_reflns_number_total             4520
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    ?
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0203(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0178
_refine_ls_restrained_S_all      1.068
_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)+(0.0188P)²+0.5935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0468
_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, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12A), C13(H13), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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 0.23202(2) 0.33237(2) 0.92336(2) 0.02514(6) Uani 1 1 d . . . . .
Cl1 Cl 0.08379(8) 0.19945(5) 1.01105(6) 0.06069(17) Uani 1 1 d . . . . .
O1 O 0.17373(16) 0.24500(12) 0.72970(11) 0.0365(3) Uani 1 1 d . . . . .
O2 O 0.39644(15) 0.19677(12) 0.86805(11) 0.0351(3) Uani 1 1 d . . . . .
O3 O 0.22185(16) 0.09574(12) 0.57962(11) 0.0390(3) Uani 1 1 d . . . . .
O4 O 0.44800(16) 0.04487(12) 0.72059(12) 0.0396(3) Uani 1 1 d . . . . .
O5 O 0.37031(14) 0.47318(11) 0.87373(11) 0.0302(3) Uani 1 1 d . . . . .
O6 O -0.02492(15) 0.59335(13) 1.13767(12) 0.0399(3) Uani 1 1 d . . . . .
O7 O 0.16561(15) 0.48398(12) 1.08021(12) 0.0377(3) Uani 1 1 d . . . . .
O8 O 0.56941(13) 0.61165(11) 0.93502(10) 0.0277(2) Uani 1 1 d . . . . .
C1 C 0.48313(18) 0.52485(14) 0.94540(14) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.0406(2) 0.52216(16) 1.06266(15) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.3756(2) 0.12945(16) 0.76410(15) 0.0279(3) Uani 1 1 d . . . . .
C4 C 0.2458(2) 0.15887(16) 0.68390(15) 0.0281(3) Uani 1 1 d . . . . .
O1W O 0.3430(2) 0.0186(2) 0.12976(15) 0.0731(6) Uani 1 1 d . . . . .
H1WA H 0.2645 0.0397 0.1709 0.110 Uiso 1 1 d R . . . .
H1WB H 0.3932 -0.0193 0.1728 0.110 Uiso 1 1 d R . . . .
O2W O 0.1461(2) 0.3971(2) 0.29731(16) 0.0699(5) Uani 1 1 d . . . . .
H2WA H 0.0946 0.4498 0.3382 0.105 Uiso 1 1 d R . . . .
H2WB H 0.1452 0.4151 0.2301 0.105 Uiso 1 1 d R . . . .
O3W O 0.0322(2) 0.43229(18) 0.60898(19) 0.0720(5) Uani 1 1 d . . . . .
H3WA H 0.0408 0.3814 0.6488 0.108 Uiso 1 1 d R . . . .
H3WB H 0.1245 0.4535 0.5972 0.108 Uiso 1 1 d R . . . .
O9 O -0.01050(18) 0.83476(15) 0.54628(12) 0.0468(4) Uani 1 1 d . . . . .
H9 H -0.0789 0.8600 0.5107 0.070 Uiso 1 1 calc GR . . . .
O10 O -0.09109(19) 0.95592(16) 0.70532(14) 0.0541(4) Uani 1 1 d . . . . .
N1 N 0.2721(2) 0.88506(17) 0.90856(16) 0.0397(4) Uani 1 1 d . . . . .
H1 H 0.297(3) 0.930(3) 0.978(3) 0.065(9) Uiso 1 1 d . . . . .
C5 C 0.1605(2) 0.91508(17) 0.84287(17) 0.0336(4) Uani 1 1 d . . . . .
H5 H 0.1119 0.9836 0.8735 0.040 Uiso 1 1 calc R . . . .
C6 C 0.3433(3) 0.7872(2) 0.8693(2) 0.0490(5) Uani 1 1 d . . . . .
H6 H 0.4218 0.7692 0.9177 0.059 Uiso 1 1 calc R . . . .
C7 C 0.3016(3) 0.7131(2) 0.7586(2) 0.0507(5) Uani 1 1 d . . . . .
H7 H 0.3494 0.6434 0.7315 0.061 Uiso 1 1 calc R . . . .
C8 C 0.1881(2) 0.74255(19) 0.68740(19) 0.0407(4) Uani 1 1 d . . . . .
H8 H 0.1592 0.6936 0.6110 0.049 Uiso 1 1 calc R . . . .
C9 C 0.1170(2) 0.84540(16) 0.73002(16) 0.0314(4) Uani 1 1 d . . . . .
C10 C -0.0072(2) 0.88445(17) 0.65964(17) 0.0351(4) Uani 1 1 d . . . . .
O11 O 0.3574(2) 0.44421(16) 0.55796(16) 0.0594(4) Uani 1 1 d . . . . .
O12 O 0.3497(2) 0.30203(17) 0.38801(15) 0.0638(5) Uani 1 1 d . . . . .
H12 H 0.2851 0.3408 0.3653 0.096 Uiso 1 1 calc GR . . . .
N2 N 0.6550(2) 0.11990(16) 0.51728(17) 0.0426(4) Uani 1 1 d . . . . .
H2 H 0.676(3) 0.053(3) 0.473(3) 0.069(9) Uiso 1 1 d . . . . .
C11 C 0.5489(2) 0.17797(18) 0.47640(18) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.4941 0.1436 0.4027 0.048 Uiso 1 1 calc R . . . .
C12 C 0.7361(3) 0.1643(2) 0.6214(2) 0.0486(5) Uani 1 1 d . . . . .
H12A H 0.8100 0.1208 0.6470 0.058 Uiso 1 1 calc R . . . .
C13 C 0.7108(3) 0.2745(2) 0.6912(2) 0.0514(5) Uani 1 1 d . . . . .
H13 H 0.7670 0.3063 0.7648 0.062 Uiso 1 1 calc R . . . .
C14 C 0.6021(3) 0.33778(19) 0.65172(19) 0.0437(5) Uani 1 1 d . . . . .
H14 H 0.5841 0.4130 0.6982 0.052 Uiso 1 1 calc R . . . .
C15 C 0.5199(2) 0.28929(17) 0.54312(17) 0.0358(4) Uani 1 1 d . . . . .
C16 C 0.3999(3) 0.35443(19) 0.4975(2) 0.0430(5) Uani 1 1 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 Cl1 2.3791(7) . ?
In1 O1 2.2289(14) . ?
In1 O2 2.2166(13) . ?
In1 O5 2.1524(13) . ?
In1 O6 2.2186(14) 2_567 ?
In1 O7 2.3268(14) . ?
In1 O8 2.2459(13) 2_667 ?
O1 C4 1.244(2) . ?
O2 C3 1.253(2) . ?
O3 C4 1.241(2) . ?
O4 C3 1.226(2) . ?
O5 C1 1.250(2) . ?
O6 In1 2.2186(14) 2_567 ?
O6 C2 1.243(2) . ?
O7 C2 1.236(2) . ?
O8 In1 2.2459(13) 2_667 ?
O8 C1 1.233(2) . ?
C1 C1 1.542(3) 2_667 ?
C2 C2 1.523(3) 2_567 ?
C3 C4 1.538(2) . ?
O1W H1WA 0.8771 . ?
O1W H1WB 0.8661 . ?
O2W H2WA 0.8515 . ?
O2W H2WB 0.8575 . ?
O3W H3WA 0.8388 . ?
O3W H3WB 0.8510 . ?
O9 H9 0.8200 . ?
O9 C10 1.296(2) . ?
O10 C10 1.196(2) . ?
N1 H1 0.84(3) . ?
N1 C5 1.323(3) . ?
N1 C6 1.328(3) . ?
C5 H5 0.9300 . ?
C5 C9 1.365(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.361(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 C10 1.486(3) . ?
O11 C16 1.197(3) . ?
O12 H12 0.8200 . ?
O12 C16 1.294(3) . ?
N2 H2 0.85(3) . ?
N2 C11 1.321(3) . ?
N2 C12 1.321(3) . ?
C11 H11 0.9300 . ?
C11 C15 1.374(3) . ?
C12 H12A 0.9300 . ?
C12 C13 1.367(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 C16 1.487(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
O1 In1 Cl1 101.38(5) . . ?
O1 In1 O7 142.45(5) . . ?
O1 In1 O8 142.62(5) . 2_667 ?
O2 In1 Cl1 91.08(5) . . ?
O2 In1 O1 72.61(5) . . ?
O2 In1 O6 144.02(5) . 2_567 ?
O2 In1 O7 144.81(5) . . ?
O2 In1 O8 75.40(5) . 2_667 ?
O5 In1 Cl1 170.30(4) . . ?
O5 In1 O1 88.04(5) . . ?
O5 In1 O2 93.95(6) . . ?
O5 In1 O6 87.78(6) . 2_567 ?
O5 In1 O7 86.32(6) . . ?
O5 In1 O8 75.30(5) . 2_667 ?
O6 In1 Cl1 93.01(5) 2_567 . ?
O6 In1 O1 71.53(5) 2_567 . ?
O6 In1 O7 71.17(5) 2_567 . ?
O6 In1 O8 138.95(5) 2_567 2_667 ?
O7 In1 Cl1 84.79(5) . . ?
O8 In1 Cl1 98.03(4) 2_667 . ?
O8 In1 O7 70.65(5) 2_667 . ?
C4 O1 In1 117.05(11) . . ?
C3 O2 In1 117.87(11) . . ?
C1 O5 In1 116.14(11) . . ?
C2 O6 In1 118.61(12) . 2_567 ?
C2 O7 In1 115.15(11) . . ?
C1 O8 In1 113.28(10) . 2_667 ?
O5 C1 C1 117.15(18) . 2_667 ?
O8 C1 O5 125.04(15) . . ?
O8 C1 C1 117.80(17) . 2_667 ?
O6 C2 C2 117.00(19) . 2_567 ?
O7 C2 O6 126.09(16) . . ?
O7 C2 C2 116.91(19) . 2_567 ?
O2 C3 C4 115.33(15) . . ?
O4 C3 O2 127.02(17) . . ?
O4 C3 C4 117.64(15) . . ?
O1 C4 C3 116.66(15) . . ?
O3 C4 O1 125.51(17) . . ?
O3 C4 C3 117.83(15) . . ?
H1WA O1W H1WB 103.1 . . ?
H2WA O2W H2WB 102.8 . . ?
H3WA O3W H3WB 104.4 . . ?
C10 O9 H9 109.5 . . ?
C5 N1 H1 118(2) . . ?
C5 N1 C6 122.2(2) . . ?
C6 N1 H1 120(2) . . ?
N1 C5 H5 120.0 . . ?
N1 C5 C9 119.90(18) . . ?
C9 C5 H5 120.0 . . ?
N1 C6 H6 119.9 . . ?
N1 C6 C7 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.1(2) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C5 C9 C8 119.07(18) . . ?
C5 C9 C10 117.58(17) . . ?
C8 C9 C10 123.35(18) . . ?
O9 C10 C9 112.62(16) . . ?
O10 C10 O9 125.24(18) . . ?
O10 C10 C9 122.12(18) . . ?
C16 O12 H12 109.5 . . ?
C11 N2 H2 119(2) . . ?
C12 N2 H2 118(2) . . ?
C12 N2 C11 122.63(19) . . ?
N2 C11 H11 120.1 . . ?
N2 C11 C15 119.8(2) . . ?
C15 C11 H11 120.1 . . ?
N2 C12 H12A 120.1 . . ?
N2 C12 C13 119.7(2) . . ?
C13 C12 H12A 120.1 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C11 C15 C16 119.86(19) . . ?
C14 C15 C11 118.9(2) . . ?
C14 C15 C16 121.22(18) . . ?
O11 C16 O12 125.8(2) . . ?
O11 C16 C15 122.2(2) . . ?
O12 C16 C15 111.93(18) . . ?

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 O10 0.88 2.15 2.993(3) 161.5 2_566
O1W H1WB O4 0.87 1.89 2.715(2) 157.8 2_656
O2W H2WA O3W 0.85 1.84 2.671(3) 166.1 2_566
O2W H2WB O7 0.86 2.10 2.951(2) 170.9 1_554
O3W H3WA O1 0.84 2.37 3.151(2) 154.6 .
O3W H3WA O6 0.84 2.44 3.039(3) 129.0 2_567
O3W H3WB O11 0.85 2.12 2.935(3) 161.1 .
O9 H9 O3 0.82 1.77 2.589(2) 174.1 2_566
N1 H1 O1W 0.84(3) 1.80(3) 2.646(3) 177(3) 1_566
C5 H5 Cl1 0.93 2.64 3.508(2) 156.6 1_565
C6 H6 O8 0.93 2.36 3.140(2) 141.7 .
C7 H7 O11 0.93 2.65 3.467(3) 146.4 .
O12 H12 O2W 0.82 1.67 2.482(3) 169.3 .
N2 H2 O3 0.85(3) 1.98(3) 2.792(2) 159(3) 2_656
N2 H2 O4 0.85(3) 2.39(3) 2.967(2) 125(2) 2_656
C11 H11 O4 0.93 2.39 2.980(2) 120.9 2_656
C12 H12A O10 0.93 2.38 3.259(3) 157.2 1_645
C13 H13 O6 0.93 2.50 3.293(3) 143.3 2_667
C13 H13 O7 0.93 2.62 3.368(3) 138.3 2_667

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 C4 O3 175.54(15) . . . . ?
In1 O1 C4 C3 -4.7(2) . . . . ?
In1 O2 C3 O4 -174.97(15) . . . . ?
In1 O2 C3 C4 5.7(2) . . . . ?
In1 O5 C1 O8 -175.68(13) . . . . ?
In1 O5 C1 C1 4.7(2) . . . 2_667 ?
In1 O6 C2 O7 171.43(16) 2_567 . . . ?
In1 O6 C2 C2 -8.5(3) 2_567 . . 2_567 ?
In1 O7 C2 O6 172.13(16) . . . . ?
In1 O7 C2 C2 -7.9(3) . . . 2_567 ?
In1 O8 C1 O5 -175.68(13) 2_667 . . . ?
In1 O8 C1 C1 3.9(2) 2_667 . . 2_667 ?
O2 C3 C4 O1 -0.6(2) . . . . ?
O2 C3 C4 O3 179.11(17) . . . . ?
O4 C3 C4 O1 -179.99(17) . . . . ?
O4 C3 C4 O3 -0.2(3) . . . . ?
N1 C5 C9 C8 1.6(3) . . . . ?
N1 C5 C9 C10 -179.09(17) . . . . ?
N1 C6 C7 C8 1.5(4) . . . . ?
C5 N1 C6 C7 -0.5(3) . . . . ?
C5 C9 C10 O9 161.78(18) . . . . ?
C5 C9 C10 O10 -16.9(3) . . . . ?
C6 N1 C5 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C5 -0.6(3) . . . . ?
C7 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 O9 -18.9(3) . . . . ?
C8 C9 C10 O10 162.4(2) . . . . ?
N2 C11 C15 C14 -0.2(3) . . . . ?
N2 C11 C15 C16 -179.68(18) . . . . ?
N2 C12 C13 C14 -0.4(4) . . . . ?
C11 N2 C12 C13 0.1(3) . . . . ?
C11 C15 C16 O11 170.8(2) . . . . ?
C11 C15 C16 O12 -8.9(3) . . . . ?
C12 N2 C11 C15 0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C11 0.0(3) . . . . ?
C13 C14 C15 C16 179.5(2) . . . . ?
C14 C15 C16 O11 -8.7(3) . . . . ?
C14 C15 C16 O12 171.7(2) . . . . ?

_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_x
_database_code_depnum_ccdc_archive 'CCDC 1525686'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cl4 In N2 O'
_chemical_formula_weight         431.83

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'
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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   Cmcm

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

_cell_length_a                   11.882(6)
_cell_length_b                   16.042(8)
_cell_length_c                   7.377(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1406.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_T_max  0.8295
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3868
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             819
_reflns_number_gt                741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0104P)²+6.0088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         819
_refine_ls_number_parameters     61
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
In1 In 0.5000 0.86236(3) 0.2500 0.02714(16) Uani 1 4 d S . .
C1 C 0.5938(5) 0.6742(4) 0.2500 0.067(2) Uani 1 2 d S . .
H1 H 0.6616 0.7032 0.2500 0.080 Uiso 1 2 calc SR . .
C2 C 0.5973(5) 0.5888(4) 0.2500 0.071(3) Uani 1 2 d S . .
H2 H 0.6663 0.5615 0.2500 0.085 Uiso 1 2 calc SR . .
C3 C 0.5000 0.5437(4) 0.2500 0.0285(15) Uani 1 4 d S . .
C4 C 0.5000 0.4513(4) 0.2500 0.0304(16) Uani 1 4 d S . .
C5 C 0.4037(5) 0.4059(4) 0.2500 0.081(3) Uani 1 2 d S . .
H5 H 0.3348 0.4334 0.2500 0.098 Uiso 1 2 calc SR . .
C6 C 0.4056(6) 0.3210(4) 0.2500 0.086(3) Uani 1 2 d S . .
H6 H 0.3383 0.2914 0.2500 0.104 Uiso 1 2 calc SR . .
N1 N 0.5000 0.7171(4) 0.2500 0.0324(14) Uani 1 4 d S . .
N2 N 0.5000 0.2812(4) 0.2500 0.051(2) Uani 1 4 d SD . .
H2A H 0.5000 0.2277(8) 0.2500 0.076 Uiso 1 4 d SD . .
O1 O 0.5000 1.0001(3) 0.2500 0.0408(14) Uani 1 4 d SD . .
H1A H 0.441(3) 1.027(4) 0.2500 0.061 Uiso 1 2 d SD . .
Cl1 Cl 0.64600(8) 0.86363(7) 0.01021(15) 0.0474(3) Uani 1 1 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 2.210(5) . ?
In1 N1 2.330(6) . ?
In1 Cl1 2.4777(14) 11_655 ?
In1 Cl1 2.4777(14) 4_655 ?
In1 Cl1 2.4777(14) . ?
In1 Cl1 2.4777(14) 10_556 ?
C1 N1 1.310(6) . ?
C1 C2 1.371(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C2 1.364(7) 11_655 ?
C3 C4 1.482(10) . ?
C4 C5 1.356(7) . ?
C4 C5 1.356(7) 11_655 ?
C5 C6 1.362(9) . ?
C5 H5 0.9300 . ?
C6 N2 1.290(7) . ?
C6 H6 0.9300 . ?
N1 C1 1.310(6) 11_655 ?
N2 C6 1.290(7) 11_655 ?
N2 H2A 0.858(10) . ?
O1 H1A 0.815(10) . ?

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 N1 180.000(1) . . ?
O1 In1 Cl1 89.53(3) . 11_655 ?
N1 In1 Cl1 90.47(3) . 11_655 ?
O1 In1 Cl1 89.53(3) . 4_655 ?
N1 In1 Cl1 90.47(3) . 4_655 ?
Cl1 In1 Cl1 91.11(7) 11_655 4_655 ?
O1 In1 Cl1 89.53(3) . . ?
N1 In1 Cl1 90.47(3) . . ?
Cl1 In1 Cl1 88.88(7) 11_655 . ?
Cl1 In1 Cl1 179.06(6) 4_655 . ?
O1 In1 Cl1 89.53(3) . 10_556 ?
N1 In1 Cl1 90.47(3) . 10_556 ?
Cl1 In1 Cl1 179.06(6) 11_655 10_556 ?
Cl1 In1 Cl1 88.88(7) 4_655 10_556 ?
Cl1 In1 Cl1 91.11(7) . 10_556 ?
N1 C1 C2 123.4(5) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C2 115.9(7) 11_655 . ?
C2 C3 C4 122.1(3) 11_655 . ?
C2 C3 C4 122.1(3) . . ?
C5 C4 C5 115.0(7) . 11_655 ?
C5 C4 C3 122.5(4) . . ?
C5 C4 C3 122.5(4) 11_655 . ?
C4 C5 C6 121.6(6) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
N2 C6 C5 120.6(6) . . ?
N2 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 N1 C1 116.6(6) 11_655 . ?
C1 N1 In1 121.7(3) 11_655 . ?
C1 N1 In1 121.7(3) . . ?
C6 N2 C6 120.8(7) . 11_655 ?
C6 N2 H2A 119.6(4) . . ?
C6 N2 H2A 119.6(4) 11_655 . ?
In1 O1 H1A 121(5) . . ?

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
N1 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C2 0.0 . . . 11_655 ?
C1 C2 C3 C4 180.0 . . . . ?
C2 C3 C4 C5 0.0 11_655 . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C2 C3 C4 C5 180.0 11_655 . . 11_655 ?
C2 C3 C4 C5 0.0 . . . 11_655 ?
C5 C4 C5 C6 0.0 11_655 . . . ?
C3 C4 C5 C6 180.0 . . . . ?
C4 C5 C6 N2 0.0 . . . . ?
C2 C1 N1 C1 0.0 . . . 11_655 ?
C2 C1 N1 In1 180.0 . . . . ?
O1 In1 N1 C1 180(22) . . . 11_655 ?
Cl1 In1 N1 C1 -45.56(4) 11_655 . . 11_655 ?
Cl1 In1 N1 C1 45.56(4) 4_655 . . 11_655 ?
Cl1 In1 N1 C1 -134.44(4) . . . 11_655 ?
Cl1 In1 N1 C1 134.44(4) 10_556 . . 11_655 ?
O1 In1 N1 C1 0(22) . . . . ?
Cl1 In1 N1 C1 134.44(4) 11_655 . . . ?
Cl1 In1 N1 C1 -134.44(4) 4_655 . . . ?
Cl1 In1 N1 C1 45.56(4) . . . . ?
Cl1 In1 N1 C1 -45.56(4) 10_556 . . . ?
C5 C6 N2 C6 0.0 . . . 11_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
O1 H1A Cl1 0.815(10) 2.80(2) 3.387(4) 130(3) 2_675
O1 H1A Cl1 0.815(10) 2.80(2) 3.387(4) 130(3) 9_675
N2 H2A Cl1 0.858(10) 2.973(6) 3.477(5) 119.5(2) 9_665
N2 H2A Cl1 0.858(10) 2.973(6) 3.477(5) 119.5(2) 12_566
N2 H2A Cl1 0.858(10) 2.973(6) 3.477(5) 119.5(2) 3_565
N2 H2A Cl1 0.858(10) 2.973(6) 3.477(5) 119.5(2) 2_665

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1525684'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
_audit_creation_date             2017-02-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Cl2 In O5, C5 H5 N, 2(H2 O)'
_chemical_formula_sum            'C13 H15 Cl2 In N O7'
_chemical_formula_weight         482.98
_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'
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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4216(11)
_cell_length_b                   20.760(3)
_cell_length_c                   10.8627(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.634(2)
_cell_angle_gamma                90
_cell_volume                     1673.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.767
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0724 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.9144. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.662
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             3522
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    ?
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.005
_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)+(0.0216P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O5A-C8
 1.26 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 O5, In1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O5A, C8, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O5(0.5) O5A(0.5)
6.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
6.b Rotating group:
 O3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), N1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.33994(3) 0.70228(2) 0.83822(2) 0.02412(8) Uani 1 1 d . U . . .
C1 C 0.2249(4) 0.81952(15) 0.7732(3) 0.0261(7) Uani 1 1 d . . . . .
C2 C 0.1701(4) 0.88791(15) 0.7471(3) 0.0244(7) Uani 1 1 d . . . . .
C3 C 0.1017(4) 0.92464(16) 0.8423(3) 0.0283(8) Uani 1 1 d . . . . .
H3 H 0.0833 0.9058 0.9186 0.034 Uiso 1 1 calc R . . . .
C4 C 0.0610(5) 0.98882(17) 0.8241(3) 0.0356(9) Uani 1 1 d . . . . .
H4 H 0.0137 1.0127 0.8880 0.043 Uiso 1 1 calc R . . . .
C5 C 0.0899(5) 1.01797(16) 0.7120(3) 0.0333(8) Uani 1 1 d . . . . .
H5 H 0.0625 1.0613 0.7000 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1599(4) 0.98174(15) 0.6178(3) 0.0288(8) Uani 1 1 d . . . . .
H6 H 0.1811 1.0013 0.5426 0.035 Uiso 1 1 calc R . . . .
C7 C 0.1992(4) 0.91720(15) 0.6330(3) 0.0218(7) Uani 1 1 d . . . . .
C8 C 0.2613(4) 0.87942(16) 0.5242(3) 0.0287(8) Uani 1 1 d D U . . .
C9 C 0.5960(5) 0.9823(2) 0.7298(4) 0.0471(10) Uani 1 1 d . . . . .
H9 H 0.5978 1.0033 0.6542 0.057 Uiso 1 1 calc R . . . .
C10 C 0.5360(5) 1.01408(18) 0.8309(4) 0.0434(10) Uani 1 1 d . . . . .
H10 H 0.4969 1.0565 0.8238 0.052 Uiso 1 1 calc R . . . .
C11 C 0.5333(5) 0.98319(17) 0.9441(3) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.5934(5) 0.92002(19) 0.9488(4) 0.0465(10) Uani 1 1 d . . . . .
H12 H 0.5942 0.8978 1.0232 0.056 Uiso 1 1 calc R . . . .
C13 C 0.6517(5) 0.8901(2) 0.8447(4) 0.0479(10) Uani 1 1 d . . . . .
H13 H 0.6911 0.8476 0.8485 0.057 Uiso 1 1 calc R . . . .
N1 N 0.6519(4) 0.92163(16) 0.7389(3) 0.0429(8) Uani 1 1 d . . . . .
H1 H 0.6891 0.9024 0.6743 0.051 Uiso 1 1 calc R . . . .
O1 O 0.3653(3) 0.79706(11) 0.72639(19) 0.0313(5) Uani 1 1 d . . . . .
O1W O 0.7920(4) 0.87442(14) 0.5336(3) 0.0531(7) Uani 1 1 d . . . . .
H1WA H 0.8718 0.8452 0.5302 0.080 Uiso 1 1 d G . . . .
H1WB H 0.7116 0.8681 0.4776 0.080 Uiso 1 1 d G . . . .
O2 O 0.1372(3) 0.78582(11) 0.8468(2) 0.0359(6) Uani 1 1 d . . . . .
O2W O 0.8426(4) 0.77481(18) 1.0123(3) 0.0643(9) Uani 1 1 d . . . . .
H2WA H 0.8772 0.7947 1.0771 0.096 Uiso 1 1 d G . . . .
H2WB H 0.9284 0.7735 0.9621 0.096 Uiso 1 1 d G . . . .
O3 O 0.4816(3) 0.75422(11) 0.9897(2) 0.0367(6) Uani 1 1 d . . . . .
H3A H 0.4583 0.7473 1.0678 0.055 Uiso 1 1 d GR . . . .
H3B H 0.5911 0.7565 1.0021 0.055 Uiso 1 1 d GR . . . .
O4 O 0.1715(3) 0.83006(11) 0.4916(2) 0.0349(6) Uani 1 1 d . . . . .
O5 O 0.3790(17) 0.8968(8) 0.4565(12) 0.033(2) Uani 0.5 1 d . U P A 1
Cl1 Cl 0.17229(13) 0.64903(4) 0.67301(8) 0.0409(2) Uani 1 1 d . . . . .
Cl2 Cl 0.64109(12) 0.67674(4) 0.76441(8) 0.0357(2) Uani 1 1 d . . . . .
O5A O 0.4091(18) 0.8989(9) 0.4759(13) 0.038(3) Uani 0.5 1 d 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 O1 2.323(2) . ?
In1 O2 2.300(2) . ?
In1 O3 2.208(2) . ?
In1 O4 2.215(2) 4_576 ?
In1 O5 2.438(16) 4_576 ?
In1 Cl1 2.4216(9) . ?
In1 Cl2 2.4539(9) . ?
C1 C2 1.502(4) . ?
C1 O1 1.261(4) . ?
C1 O2 1.258(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.403(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(4) . ?
C7 C8 1.502(4) . ?
C8 O4 1.267(4) . ?
C8 O5 1.212(12) . ?
C8 O5A 1.294(12) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(5) . ?
C9 N1 1.329(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(5) . ?
C11 C11 1.496(7) 3_677 ?
C11 C12 1.386(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(5) . ?
C13 H13 0.9300 . ?
C13 N1 1.323(5) . ?
N1 H1 0.8600 . ?
O1W H1WA 0.8494 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8498 . ?
O2W H2WB 0.8499 . ?
O3 H3A 0.8822 . ?
O3 H3B 0.8214 . ?
O4 In1 2.215(2) 4_575 ?
O5 In1 2.438(16) 4_575 ?

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 O5 168.5(3) . 4_576 ?
O1 In1 Cl1 92.67(6) . . ?
O1 In1 Cl2 85.65(6) . . ?
O2 In1 O1 56.30(8) . . ?
O2 In1 O5 133.1(3) . 4_576 ?
O2 In1 Cl1 92.95(7) . . ?
O2 In1 Cl2 141.19(6) . . ?
O3 In1 O1 86.12(8) . . ?
O3 In1 O2 84.24(9) . . ?
O3 In1 O4 81.63(9) . 4_576 ?
O3 In1 O5 88.4(4) . 4_576 ?
O3 In1 Cl1 177.16(7) . . ?
O3 In1 Cl2 86.01(7) . . ?
O4 In1 O1 134.90(8) 4_576 . ?
O4 In1 O2 79.29(8) 4_576 . ?
O4 In1 O5 53.8(3) 4_576 4_576 ?
O4 In1 Cl1 97.46(7) 4_576 . ?
O4 In1 Cl2 135.97(7) 4_576 . ?
O5 In1 Cl2 83.9(3) 4_576 . ?
Cl1 In1 O5 93.2(4) . 4_576 ?
Cl1 In1 Cl2 96.47(3) . . ?
O1 C1 C2 119.7(3) . . ?
O2 C1 C2 120.2(3) . . ?
O2 C1 O1 119.9(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C7 119.2(3) . . ?
C7 C2 C1 121.9(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C8 121.8(3) . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 C8 118.8(3) . . ?
O4 C8 C7 118.1(3) . . ?
O4 C8 O5A 125.8(9) . . ?
O5 C8 C7 124.3(8) . . ?
O5 C8 O4 117.0(8) . . ?
O5A C8 C7 116.0(8) . . ?
C10 C9 H9 119.8 . . ?
N1 C9 H9 119.8 . . ?
N1 C9 C10 120.4(4) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C11 121.1(4) . 3_677 ?
C12 C11 C10 117.2(3) . . ?
C12 C11 C11 121.6(4) . 3_677 ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
N1 C13 C12 120.1(4) . . ?
N1 C13 H13 120.0 . . ?
C9 N1 H1 119.2 . . ?
C13 N1 C9 121.7(4) . . ?
C13 N1 H1 119.2 . . ?
C1 O1 In1 91.28(19) . . ?
H1WA O1W H1WB 109.5 . . ?
C1 O2 In1 92.45(19) . . ?
H2WA O2W H2WB 109.5 . . ?
In1 O3 H3A 122.4 . . ?
In1 O3 H3B 126.7 . . ?
H3A O3 H3B 94.1 . . ?
C8 O4 In1 98.7(2) . 4_575 ?
C8 O5 In1 89.5(8) . 4_575 ?

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
C9 H9 O5 0.93 2.41 3.233(16) 148.0 3_676
C9 H9 O5A 0.93 2.47 3.328(17) 152.7 3_676
C10 H10 Cl2 0.93 2.85 3.758(4) 164.7 2_656
C13 H13 O2W 0.93 2.57 3.302(6) 136.0 .
N1 H1 O1W 0.86 1.82 2.673(4) 169.8 .
O1W H1WA O2W 0.85 2.51 3.130(5) 130.9 4_575
O1W H1WA O4 0.85 2.30 3.011(4) 141.8 1_655
O1W H1WB O5 0.85 2.54 3.189(14) 133.5 .
O1W H1WB Cl2 0.85 2.54 3.278(3) 146.3 4_575
O1W H1WB O5A 0.85 2.33 2.937(15) 128.2 .
O2W H2WA Cl1 0.85 2.67 3.360(3) 139.6 4_676
O2W H2WA Cl2 0.85 2.79 3.314(3) 121.9 4_576
O2W H2WB O2 0.85 2.04 2.879(4) 170.8 1_655
O3 H3A O1 0.88 2.09 2.935(3) 160.6 4_576
O3 H3A Cl2 0.88 2.95 3.487(2) 120.7 4_576
O3 H3B O2W 0.82 1.91 2.718(4) 169.9 .

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
C1 C2 C3 C4 175.7(3) . . . . ?
C1 C2 C7 C6 -174.6(3) . . . . ?
C1 C2 C7 C8 9.3(5) . . . . ?
C2 C1 O1 In1 173.7(3) . . . . ?
C2 C1 O2 In1 -173.7(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C2 C7 C8 O4 53.5(4) . . . . ?
C2 C7 C8 O5 -135.3(9) . . . . ?
C2 C7 C8 O5A -123.0(9) . . . . ?
C3 C2 C7 C6 0.2(5) . . . . ?
C3 C2 C7 C8 -176.0(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 C2 -1.0(5) . . . . ?
C5 C6 C7 C8 175.3(3) . . . . ?
C6 C7 C8 O4 -122.7(3) . . . . ?
C6 C7 C8 O5 48.5(10) . . . . ?
C6 C7 C8 O5A 60.8(9) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C7 C8 O4 In1 -177.7(2) . . . 4_575 ?
C7 C8 O5 In1 179.3(3) . . . 4_575 ?
C9 C10 C11 C11 -179.5(4) . . . 3_677 ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C9 N1 C13 -0.1(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C11 C12 C13 179.2(4) 3_677 . . . ?
C11 C12 C13 N1 0.4(6) . . . . ?
C12 C13 N1 C9 -0.2(6) . . . . ?
N1 C9 C10 C11 0.1(6) . . . . ?
O1 C1 C2 C3 -140.4(3) . . . . ?
O1 C1 C2 C7 34.4(5) . . . . ?
O1 C1 O2 In1 2.3(3) . . . . ?
O2 C1 C2 C3 35.7(5) . . . . ?
O2 C1 C2 C7 -149.5(3) . . . . ?
O2 C1 O1 In1 -2.3(3) . . . . ?
O4 C8 O5 In1 -9.4(8) . . . 4_575 ?
O5 C8 O4 In1 10.5(9) . . . 4_575 ?
O5A C8 O4 In1 -1.5(10) . . . 4_575 ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1525685'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
_audit_creation_date             2017-02-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Cl In N O8'
_chemical_formula_sum            'C14 H13 Cl In N O8'
_chemical_formula_weight         473.52
_chemical_absolute_configuration .
_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'
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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3473(9)
_cell_length_b                   10.8184(13)
_cell_length_c                   20.154(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1601.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    838
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.51
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0810 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.8380. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.963
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.018
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.006
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.021
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2485
_reflns_number_total             3270
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    ?
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.16(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.050
_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)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.84(8)
 0.16(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Rotating group:
 O7(H7A,H7B), O8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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 0.47945(9) 0.43719(6) 0.13679(4) 0.0240(2) Uani 1 1 d . . . . .
Cl Cl 0.2597(4) 0.6028(3) 0.1370(2) 0.0419(8) Uani 1 1 d . . . . .
O1 O 0.5033(14) 0.4344(7) 0.2442(3) 0.0332(18) Uani 1 1 d . . . . .
O2 O 0.3547(11) 0.2668(7) 0.2786(4) 0.029(2) Uani 1 1 d . . . . .
O3 O 0.9325(9) 0.3591(6) 0.1296(4) 0.0266(17) Uani 1 1 d . . . . .
O4 O 0.6561(9) 0.2796(6) 0.1340(5) 0.0277(17) Uani 1 1 d . . . . .
O5 O 0.8620(12) 0.2177(7) -0.0003(4) 0.038(2) Uani 1 1 d . . . . .
O6 O 1.0107(14) 0.0491(7) -0.0333(3) 0.042(2) Uani 1 1 d . . . . .
O7 O 0.2755(10) 0.2941(6) 0.1488(4) 0.029(2) Uani 1 1 d . . . . .
H7A H 0.1650 0.3223 0.1406 0.043 Uiso 1 1 d GR . . . .
H7B H 0.2759 0.2654 0.1898 0.043 Uiso 1 1 d GR . . . .
O8 O 0.7157(9) 0.5622(7) 0.1426(5) 0.0319(18) Uani 1 1 d . . . . .
H8A H 0.7023 0.6147 0.1754 0.048 Uiso 1 1 d GR . . . .
H8B H 0.8213 0.5330 0.1478 0.048 Uiso 1 1 d GR . . . .
N1 N 0.5500(12) 0.5705(9) 0.4303(4) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.5852 0.6457 0.4354 0.039 Uiso 1 1 calc R . . . .
C1 C 0.4318(17) 0.3371(10) 0.4132(6) 0.034(3) Uani 1 1 d . . . . .
H1A H 0.3864 0.2575 0.4078 0.041 Uiso 1 1 calc R . . . .
C2 C 0.519(3) 0.5036(11) 0.4828(6) 0.042(4) Uani 1 1 d . . . . .
H2 H 0.5362 0.5371 0.5249 0.050 Uiso 1 1 calc R . . . .
C3 C 0.462(3) 0.3843(12) 0.4762(6) 0.051(5) Uani 1 1 d . . . . .
H3 H 0.4438 0.3352 0.5135 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5287(15) 0.5263(9) 0.3689(6) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.5548 0.5763 0.3325 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4691(15) 0.4084(8) 0.3591(5) 0.024(2) Uani 1 1 d . . . . .
C6 C 0.4395(15) 0.3649(10) 0.2879(5) 0.022(3) Uani 1 1 d . . . . .
C7 C 0.8236(13) 0.2717(9) 0.1311(6) 0.022(2) Uani 1 1 d . . . . .
C8 C 0.9015(12) 0.1411(8) 0.1345(6) 0.018(2) Uani 1 1 d . . . . .
C9 C 0.9167(16) 0.0934(11) 0.1986(6) 0.030(3) Uani 1 1 d . . . . .
H9 H 0.8796 0.1400 0.2349 0.036 Uiso 1 1 calc R . . . .
C10 C 0.987(2) -0.0233(10) 0.2076(5) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.9976 -0.0551 0.2503 0.045 Uiso 1 1 calc R . . . .
C11 C 1.0413(18) -0.0931(11) 0.1548(5) 0.038(3) Uani 1 1 d . . . . .
H11 H 1.0892 -0.1716 0.1615 0.046 Uiso 1 1 calc R . . . .
C12 C 1.0249(16) -0.0467(10) 0.0921(5) 0.029(2) Uani 1 1 d . . . . .
H12 H 1.0603 -0.0952 0.0563 0.034 Uiso 1 1 calc R . . . .
C13 C 0.9563(14) 0.0716(11) 0.0803(4) 0.020(2) Uani 1 1 d . . . . .
C14 C 0.9409(16) 0.1177(11) 0.0109(5) 0.027(3) Uani 1 1 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 Cl 2.412(3) . ?
In1 O1 2.173(6) . ?
In1 O4 2.144(7) . ?
In1 O6 2.103(6) 4_455 ?
In1 O7 2.168(7) . ?
In1 O8 2.204(7) . ?
O1 C6 1.249(12) . ?
O2 C6 1.244(12) . ?
O3 C7 1.238(11) . ?
O4 C7 1.235(11) . ?
O5 C14 1.248(13) . ?
O6 In1 2.103(6) 4 ?
O6 C14 1.269(12) . ?
O7 H7A 0.8824 . ?
O7 H7B 0.8816 . ?
O8 H8A 0.8771 . ?
O8 H8B 0.8434 . ?
N1 H1 0.8600 . ?
N1 C2 1.302(13) . ?
N1 C4 1.337(12) . ?
C1 H1A 0.9300 . ?
C1 C3 1.388(15) . ?
C1 C5 1.362(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(18) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.363(12) . ?
C5 C6 1.527(14) . ?
C7 C8 1.526(13) . ?
C8 C9 1.396(15) . ?
C8 C13 1.385(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.364(14) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(14) . ?
C13 C14 1.489(13) . ?

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 Cl 93.6(3) . . ?
O1 In1 O8 83.8(3) . . ?
O4 In1 Cl 175.1(2) . . ?
O4 In1 O1 88.1(4) . . ?
O4 In1 O7 81.6(3) . . ?
O4 In1 O8 90.7(3) . . ?
O6 In1 Cl 91.3(3) 4_455 . ?
O6 In1 O1 168.6(3) 4_455 . ?
O6 In1 O4 87.9(4) 4_455 . ?
O6 In1 O7 103.7(3) 4_455 . ?
O6 In1 O8 85.6(4) 4_455 . ?
O7 In1 Cl 93.9(2) . . ?
O7 In1 O1 86.2(3) . . ?
O7 In1 O8 167.6(3) . . ?
O8 In1 Cl 94.1(2) . . ?
C6 O1 In1 132.8(8) . . ?
C7 O4 In1 131.3(7) . . ?
C14 O6 In1 127.7(8) . 4 ?
In1 O7 H7A 111.6 . . ?
In1 O7 H7B 110.7 . . ?
H7A O7 H7B 107.5 . . ?
In1 O8 H8A 110.4 . . ?
In1 O8 H8B 120.1 . . ?
H8A O8 H8B 104.6 . . ?
C2 N1 H1 118.9 . . ?
C2 N1 C4 122.3(10) . . ?
C4 N1 H1 118.9 . . ?
C3 C1 H1A 120.3 . . ?
C5 C1 H1A 120.3 . . ?
C5 C1 C3 119.4(11) . . ?
N1 C2 H2 120.0 . . ?
N1 C2 C3 120.0(11) . . ?
C3 C2 H2 120.0 . . ?
C1 C3 H3 120.4 . . ?
C2 C3 C1 119.2(11) . . ?
C2 C3 H3 120.4 . . ?
N1 C4 H4 119.8 . . ?
N1 C4 C5 120.3(11) . . ?
C5 C4 H4 119.8 . . ?
C1 C5 C4 118.7(11) . . ?
C1 C5 C6 123.2(10) . . ?
C4 C5 C6 118.0(10) . . ?
O1 C6 C5 115.0(10) . . ?
O2 C6 O1 126.5(10) . . ?
O2 C6 C5 118.4(9) . . ?
O3 C7 C8 117.7(8) . . ?
O4 C7 O3 126.3(10) . . ?
O4 C7 C8 115.8(9) . . ?
C9 C8 C7 114.5(10) . . ?
C13 C8 C7 125.2(11) . . ?
C13 C8 C9 120.4(9) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(11) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(10) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(11) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(10) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 118.0(9) . . ?
C8 C13 C14 122.4(11) . . ?
C12 C13 C14 119.6(10) . . ?
O5 C14 O6 124.5(11) . . ?
O5 C14 C13 119.8(10) . . ?
O6 C14 C13 115.7(10) . . ?

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
O7 H7A O3 0.88 1.77 2.645(10) 171.8 1_455
O7 H7B O2 0.88 1.88 2.695(12) 152.7 .
O8 H8A O2 0.88 1.94 2.774(11) 159.4 3_655
O8 H8B O3 0.84 2.08 2.726(10) 132.6 .
N1 H1 O5 0.86 2.00 2.760(12) 146.4 2_665
N1 H1 O7 0.86 2.55 3.169(12) 129.6 3_655
C2 H2 O3 0.93 2.40 3.329(13) 174.7 2_665
C3 H3 Cl 0.93 2.98 3.630(15) 128.3 2_565

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 C6 O2 7.7(19) . . . . ?
In1 O1 C6 C5 -171.4(7) . . . . ?
In1 O4 C7 O3 1(2) . . . . ?
In1 O4 C7 C8 176.2(8) . . . . ?
In1 O6 C14 O5 -11.3(18) 4 . . . ?
In1 O6 C14 C13 168.2(7) 4 . . . ?
O3 C7 C8 C9 94.3(12) . . . . ?
O3 C7 C8 C13 -85.2(14) . . . . ?
O4 C7 C8 C9 -81.6(14) . . . . ?
O4 C7 C8 C13 98.9(14) . . . . ?
N1 C2 C3 C1 -2(3) . . . . ?
N1 C4 C5 C1 0.0(17) . . . . ?
N1 C4 C5 C6 177.4(9) . . . . ?
C1 C5 C6 O1 -170.7(11) . . . . ?
C1 C5 C6 O2 10.1(16) . . . . ?
C2 N1 C4 C5 1.5(19) . . . . ?
C3 C1 C5 C4 -2.5(19) . . . . ?
C3 C1 C5 C6 -179.7(13) . . . . ?
C4 N1 C2 C3 0(3) . . . . ?
C4 C5 C6 O1 12.1(16) . . . . ?
C4 C5 C6 O2 -167.1(11) . . . . ?
C5 C1 C3 C2 4(3) . . . . ?
C7 C8 C9 C10 -179.4(10) . . . . ?
C7 C8 C13 C12 180.0(9) . . . . ?
C7 C8 C13 C14 -1.3(15) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
C8 C13 C14 O5 -6.4(16) . . . . ?
C8 C13 C14 O6 174.0(10) . . . . ?
C9 C8 C13 C12 0.5(14) . . . . ?
C9 C8 C13 C14 179.2(10) . . . . ?
C9 C10 C11 C12 0(2) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C12 C13 C8 -1.1(18) . . . . ?
C11 C12 C13 C14 -179.9(12) . . . . ?
C12 C13 C14 O5 172.4(11) . . . . ?
C12 C13 C14 O6 -7.2(16) . . . . ?
C13 C8 C9 C10 0.2(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.84(8)
2 0.16(8)

