# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_d1584
_database_code_depnum_ccdc_archive 'CCDC 1568434'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H2 In O8, C4 H6 N2'
_chemical_formula_sum            'C14 H8 In N2 O8'
_chemical_formula_weight         447.04

# start Validation Reply Form
_vrf_PLAT250_d1584               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.5 Note  
RESPONSE: This has been checked the the structure model appears
correct. 
;
_vrf_PLAT601_d1584               
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        141 Ang3  
RESPONSE: No other significant density is visible in a differnce
Fourier map. Please note SQUEEZE in PLATON (Spek, 2009) was NOT
used. 
;
# end Validation Reply Form


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'

_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'
'-y+1/2, x, z+1/2'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'y+1/2, x+1/2, -z'
'-x, y+1/2, -z+1/2'
'-y, -x, -z'
'-x, -y, -z'
'y-1/2, -x, -z-1/2'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'-y-1/2, -x-1/2, z'
'x, -y-1/2, z-1/2'
'y, x, z'

_cell_length_a                   12.5808(3)
_cell_length_b                   12.5808(3)
_cell_length_c                   12.9625(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2051.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    8016
_cell_measurement_theta_min      4.97
_cell_measurement_theta_max      67.00

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.014
_exptl_absorpt_coefficient_mu    9.561
_shelx_estimated_absorpt_T_min   0.419
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40927
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.971
_diffrn_reflns_theta_max         67.458
_diffrn_reflns_theta_full        67.458
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             988
_reflns_number_gt                668
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0393P)²+21.3030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         988
_refine_ls_number_parameters     61
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.131
_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_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 0.2500 0.7500 0.7500 0.0182(3) Uani 1 4 d S T P . .
O1 O 0.2379(4) 0.6353(4) 0.9028(3) 0.0311(11) Uani 1 1 d . . . . .
O2 O 0.1029(4) 0.6890(5) 0.8102(3) 0.0387(13) Uani 1 1 d . . . . .
C1 C 0.0653(7) 0.5696(7) 0.9458(4) 0.0368(18) Uani 1 1 d . U . . .
C2 C -0.0033(8) 0.5033(8) 0.8933(7) 0.041(3) Uani 1 2 d S TU P . .
H2 H -0.0049 0.5049 0.8201 0.049 Uiso 1 2 calc R U P . .
C3 C 0.1415(7) 0.6358(6) 0.8845(5) 0.0313(16) Uani 1 1 d . U . . .
C1S C 0.4529(16) 0.4448(14) 0.9561(11) 0.055(3) Uani 0.25 1 d G U P A -1
N1S N 0.5534(18) 0.4275(19) 1.003(2) 0.055(3) Uani 0.25 1 d DG U P A -1
C2S C 0.562(2) 0.497(2) 1.0891(17) 0.055(3) Uani 0.25 1 d G U P A -1
H2SA H 0.6209 0.5020 1.1345 0.066 Uiso 0.25 1 calc R U P A -1
C3S C 0.466(2) 0.557(2) 1.0955(14) 0.055(3) Uani 0.25 1 d G U P A -1
H3SA H 0.4506 0.6093 1.1459 0.066 Uiso 0.25 1 calc R U P A -1
N2S N 0.3991(15) 0.525(2) 1.0133(18) 0.055(3) Uani 0.25 1 d DG U P A -1
H2S H 0.3353 0.5499 1.0001 0.066 Uiso 0.25 1 calc R U P A -1
C4S C 0.414(3) 0.393(3) 0.8698(19) 0.055(3) Uani 0.25 1 d D U P A -1
H4SA H 0.4623 0.3348 0.8509 0.082 Uiso 0.25 1 calc R U P A -1
H4SB H 0.4086 0.4431 0.8123 0.082 Uiso 0.25 1 calc R U P A -1
H4SC H 0.3435 0.3636 0.8850 0.082 Uiso 0.25 1 calc R U P A -1


_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 O2 2.151(5) 3_565 ?
In1 O2 2.151(5) 12_667 ?
In1 O2 2.151(5) 10_567 ?
In1 O2 2.151(5) . ?
In1 O1 2.455(4) 3_565 ?
In1 O1 2.455(4) 10_567 ?
In1 O1 2.455(4) 12_667 ?
In1 O1 2.455(4) . ?
In1 C3 2.639(6) 3_565 ?
In1 C3 2.639(6) 12_667 ?
In1 C3 2.639(6) 10_567 ?
In1 C3 2.639(6) . ?
O1 C3 1.235(9) . ?
O2 C3 1.270(9) . ?
C1 C2 1.380(8) . ?
C1 C1 1.407(11) 6_457 ?
C1 C3 1.498(9) . ?
C2 C1 1.380(8) 14_665 ?
C2 H2 0.9500 . ?
C1S C4S 1.39(3) . ?
C1S N1S 1.4200 . ?
C1S N2S 1.4200 . ?
N1S C2S 1.4200 . ?
C2S C3S 1.4200 . ?
C2S H2SA 0.9500 . ?
C3S N2S 1.4200 . ?
C3S H3SA 0.9500 . ?
N2S H2S 0.8800 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?

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
O2 In1 O2 97.56(8) 3_565 12_667 ?
O2 In1 O2 97.56(8) 3_565 10_567 ?
O2 In1 O2 137.5(2) 12_667 10_567 ?
O2 In1 O2 137.5(2) 3_565 . ?
O2 In1 O2 97.56(8) 12_667 . ?
O2 In1 O2 97.56(8) 10_567 . ?
O2 In1 O1 56.23(18) 3_565 3_565 ?
O2 In1 O1 140.93(17) 12_667 3_565 ?
O2 In1 O1 78.99(17) 10_567 3_565 ?
O2 In1 O1 88.31(18) . 3_565 ?
O2 In1 O1 140.93(17) 3_565 10_567 ?
O2 In1 O1 88.31(18) 12_667 10_567 ?
O2 In1 O1 56.23(18) 10_567 10_567 ?
O2 In1 O1 78.99(17) . 10_567 ?
O1 In1 O1 130.61(14) 3_565 10_567 ?
O2 In1 O1 78.99(17) 3_565 12_667 ?
O2 In1 O1 56.23(18) 12_667 12_667 ?
O2 In1 O1 88.31(18) 10_567 12_667 ?
O2 In1 O1 140.93(17) . 12_667 ?
O1 In1 O1 130.61(14) 3_565 12_667 ?
O1 In1 O1 72.4(2) 10_567 12_667 ?
O2 In1 O1 88.31(18) 3_565 . ?
O2 In1 O1 78.99(17) 12_667 . ?
O2 In1 O1 140.93(17) 10_567 . ?
O2 In1 O1 56.23(18) . . ?
O1 In1 O1 72.4(2) 3_565 . ?
O1 In1 O1 130.61(14) 10_567 . ?
O1 In1 O1 130.61(14) 12_667 . ?
O2 In1 C3 28.5(2) 3_565 3_565 ?
O2 In1 C3 121.6(3) 12_667 3_565 ?
O2 In1 C3 87.5(2) 10_567 3_565 ?
O2 In1 C3 113.6(2) . 3_565 ?
O1 In1 C3 27.8(2) 3_565 3_565 ?
O1 In1 C3 143.4(2) 10_567 3_565 ?
O1 In1 C3 105.24(19) 12_667 3_565 ?
O1 In1 C3 79.56(17) . 3_565 ?
O2 In1 C3 87.5(2) 3_565 12_667 ?
O2 In1 C3 28.5(2) 12_667 12_667 ?
O2 In1 C3 113.6(2) 10_567 12_667 ?
O2 In1 C3 121.6(3) . 12_667 ?
O1 In1 C3 143.4(2) 3_565 12_667 ?
O1 In1 C3 79.56(17) 10_567 12_667 ?
O1 In1 C3 27.8(2) 12_667 12_667 ?
O1 In1 C3 105.24(19) . 12_667 ?
C3 In1 C3 115.89(15) 3_565 12_667 ?
O2 In1 C3 121.6(3) 3_565 10_567 ?
O2 In1 C3 113.6(2) 12_667 10_567 ?
O2 In1 C3 28.5(2) 10_567 10_567 ?
O2 In1 C3 87.5(2) . 10_567 ?
O1 In1 C3 105.24(19) 3_565 10_567 ?
O1 In1 C3 27.8(2) 10_567 10_567 ?
O1 In1 C3 79.56(17) 12_667 10_567 ?
O1 In1 C3 143.4(2) . 10_567 ?
C3 In1 C3 115.89(15) 3_565 10_567 ?
C3 In1 C3 97.3(3) 12_667 10_567 ?
O2 In1 C3 113.6(2) 3_565 . ?
O2 In1 C3 87.5(2) 12_667 . ?
O2 In1 C3 121.6(3) 10_567 . ?
O2 In1 C3 28.5(2) . . ?
O1 In1 C3 79.56(17) 3_565 . ?
O1 In1 C3 105.24(19) 10_567 . ?
O1 In1 C3 143.4(2) 12_667 . ?
O1 In1 C3 27.8(2) . . ?
C3 In1 C3 97.3(3) 3_565 . ?
C3 In1 C3 115.88(15) 12_667 . ?
C3 In1 C3 115.89(15) 10_567 . ?
C3 O1 In1 84.4(4) . . ?
C3 O2 In1 97.7(4) . . ?
C2 C1 C1 119.5(4) . 6_457 ?
C2 C1 C3 118.4(5) . . ?
C1 C1 C3 121.7(4) 6_457 . ?
C1 C2 C1 120.9(8) 14_665 . ?
C1 C2 H2 119.5 14_665 . ?
C1 C2 H2 119.5 . . ?
O1 C3 O2 121.6(6) . . ?
O1 C3 C1 121.6(7) . . ?
O2 C3 C1 116.7(7) . . ?
O1 C3 In1 67.8(3) . . ?
O2 C3 In1 53.9(3) . . ?
C1 C3 In1 169.7(5) . . ?
C4S C1S N1S 126.0(5) . . ?
C4S C1S N2S 126.0(5) . . ?
N1S C1S N2S 108.0 . . ?
C1S N1S C2S 108.0 . . ?
C3S C2S N1S 108.0 . . ?
C3S C2S H2SA 126.0 . . ?
N1S C2S H2SA 126.0 . . ?
C2S C3S N2S 108.0 . . ?
C2S C3S H3SA 126.0 . . ?
N2S C3S H3SA 126.0 . . ?
C3S N2S C1S 108.0 . . ?
C3S N2S H2S 126.0 . . ?
C1S N2S H2S 126.0 . . ?
C1S C4S H4SA 109.5 . . ?
C1S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C1S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?

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
C1 C1 C2 C1 2(3) 6_457 . . 14_665 ?
C3 C1 C2 C1 175.1(8) . . . 14_665 ?
In1 O1 C3 O2 -1.8(7) . . . . ?
In1 O1 C3 C1 175.2(7) . . . . ?
In1 O2 C3 O1 2.1(8) . . . . ?
In1 O2 C3 C1 -175.0(6) . . . . ?
C2 C1 C3 O1 -127.5(10) . . . . ?
C1 C1 C3 O1 45.8(17) 6_457 . . . ?
C2 C1 C3 O2 49.6(14) . . . . ?
C1 C1 C3 O2 -137.1(12) 6_457 . . . ?
C2 C1 C3 In1 27(4) . . . . ?
C1 C1 C3 In1 -160(3) 6_457 . . . ?
C4S C1S N1S C2S -179.99(14) . . . . ?
N2S C1S N1S C2S 0.0 . . . . ?
C1S N1S C2S C3S 0.0 . . . . ?
N1S C2S C3S N2S 0.0 . . . . ?
C2S C3S N2S C1S 0.0 . . . . ?
C4S C1S N2S C3S 179.99(14) . . . . ?
N1S C1S N2S C3S 0.0 . . . . ?

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
N2S H2S O1 0.88 2.06 2.85(2) 148.1 .

_refine_diff_density_max         0.749
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.137

