# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 1832922'
_audit_update_record             
;
2018-09-20 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;
_audit_creation_date             2018-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I16 Sb4, 4(C4 H12 N), 2(H2 O)'
_chemical_formula_sum            'C16 H52 I16 N4 O2 Sb4'
_chemical_formula_weight         2850.01
_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'
I I -0.4742 1.8119 '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'
Sb Sb -0.5866 1.5461 '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                   11.142(5)
_cell_length_b                   11.794(4)
_cell_length_c                   13.105(4)
_cell_angle_alpha                65.193(13)
_cell_angle_beta                 77.627(17)
_cell_angle_gamma                89.043(16)
_cell_volume                     1521.6(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.438
_shelx_estimated_absorpt_T_min   0.242
_exptl_absorpt_coefficient_mu    9.892
_exptl_absorpt_correction_T_max  0.372
_exptl_absorpt_correction_T_min  0.317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1244
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47233
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.565
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5960
_reflns_number_total             6814
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.646
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.140
_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)+4.5843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1D,H1E)
2.b Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), N2(H2D,
 H2E,H2F), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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
I1 I 0.19369(4) -0.31073(4) 0.39290(4) 0.06257(12) Uani 1 1 d . . . . .
I2 I 0.19572(3) -0.35756(3) 0.71099(3) 0.04214(9) Uani 1 1 d . . . . .
I3 I 0.34415(3) -0.00936(3) 0.43976(3) 0.04287(9) Uani 1 1 d . . . . .
I4 I -0.00003(3) 0.03298(3) 0.30598(3) 0.03865(8) Uani 1 1 d . . . . .
I5 I 0.14136(3) 0.33033(3) 0.38749(3) 0.04486(9) Uani 1 1 d . . . . .
I6 I 0.48278(3) 0.35413(4) 0.17834(4) 0.05436(11) Uani 1 1 d . . . . .
I7 I 0.18409(3) 0.38754(3) 0.02445(3) 0.04602(10) Uani 1 1 d . . . . .
I8 I 0.38055(4) 0.08018(3) 0.07926(3) 0.04888(10) Uani 1 1 d . . . . .
Sb1 Sb 0.10056(3) -0.18497(3) 0.52942(2) 0.03065(8) Uani 1 1 d . . . . .
Sb2 Sb 0.26703(3) 0.20675(3) 0.21878(2) 0.03022(8) Uani 1 1 d . . . . .
N3 N 0.1476(5) 0.7328(4) -0.0588(4) 0.0488(11) Uani 1 1 d . . . . .
H3A H 0.072047 0.739578 -0.071918 0.073 Uiso 1 1 calc GR . . . .
H3B H 0.170505 0.656667 -0.047970 0.073 Uiso 1 1 calc GR . . . .
H3C H 0.199999 0.790215 -0.119194 0.073 Uiso 1 1 calc GR . . . .
C0AA C 0.1478(5) 0.7530(5) 0.0484(4) 0.0429(11) Uani 1 1 d . . . . .
C1 C 0.2767(6) 0.7336(9) 0.0687(6) 0.081(2) Uani 1 1 d . . . . .
H1A H 0.335416 0.786436 -0.000298 0.122 Uiso 1 1 calc GR . . . .
H1B H 0.292615 0.647492 0.088754 0.122 Uiso 1 1 calc GR . . . .
H1C H 0.283929 0.754507 0.130619 0.122 Uiso 1 1 calc GR . . . .
C2 C 0.1099(10) 0.8829(7) 0.0239(8) 0.103(3) Uani 1 1 d . . . . .
H2A H 0.167865 0.942615 -0.041635 0.154 Uiso 1 1 calc GR . . . .
H2B H 0.108138 0.899444 0.089928 0.154 Uiso 1 1 calc GR . . . .
H2C H 0.029295 0.889634 0.007766 0.154 Uiso 1 1 calc GR . . . .
C4 C 0.0533(6) 0.6553(7) 0.1470(5) 0.0647(17) Uani 1 1 d . . . . .
H4A H -0.025524 0.663464 0.127155 0.097 Uiso 1 1 calc GR . . . .
H4B H 0.047159 0.667687 0.215709 0.097 Uiso 1 1 calc GR . . . .
H4C H 0.078587 0.573007 0.160219 0.097 Uiso 1 1 calc GR . . . .
N2 N 0.4532(5) 1.1556(5) -0.2577(5) 0.0605(13) Uani 1 1 d . . . . .
H2D H 0.533098 1.168125 -0.291789 0.091 Uiso 1 1 calc GR . . . .
H2E H 0.419707 1.091051 -0.263170 0.091 Uiso 1 1 calc GR . . . .
H2F H 0.444226 1.139309 -0.183569 0.091 Uiso 1 1 calc GR . . . .
C5 C 0.3897(6) 1.2721(6) -0.3163(6) 0.0585(15) Uani 1 1 d . . . . .
C6 C 0.4412(8) 1.3730(7) -0.2878(8) 0.089(3) Uani 1 1 d . . . . .
H6A H 0.402744 1.449257 -0.321442 0.133 Uiso 1 1 calc GR . . . .
H6B H 0.528654 1.387974 -0.318675 0.133 Uiso 1 1 calc GR . . . .
H6C H 0.424193 1.344708 -0.205578 0.133 Uiso 1 1 calc GR . . . .
C7 C 0.2532(7) 1.2416(9) -0.2635(9) 0.100(3) Uani 1 1 d . . . . .
H7A H 0.223477 1.176495 -0.279869 0.149 Uiso 1 1 calc GR . . . .
H7B H 0.210504 1.315112 -0.295655 0.149 Uiso 1 1 calc GR . . . .
H7C H 0.238849 1.213719 -0.181457 0.149 Uiso 1 1 calc GR . . . .
C8 C 0.4234(8) 1.3048(8) -0.4432(7) 0.092(3) Uani 1 1 d . . . . .
H8A H 0.394246 1.237068 -0.456398 0.138 Uiso 1 1 calc GR . . . .
H8B H 0.511441 1.318733 -0.470381 0.138 Uiso 1 1 calc GR . . . .
H8C H 0.386227 1.379462 -0.484089 0.138 Uiso 1 1 calc GR . . . .
O1 O 0.3314(4) 0.9297(5) -0.2538(4) 0.0621(11) Uani 1 1 d . . . . .
H1D H 0.391080 0.883778 -0.253643 0.093 Uiso 1 1 d G . . . .
H1E H 0.302428 0.934439 -0.310351 0.093 Uiso 1 1 d G . . . .


_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
I1 Sb1 2.8031(8) . ?
I2 Sb1 2.8061(9) . ?
I3 Sb1 3.1329(12) . ?
I3 Sb2 3.2281(10) . ?
I4 Sb1 3.3560(9) 2_556 ?
I4 Sb1 3.3810(10) . ?
I4 Sb2 3.3378(13) . ?
I5 Sb1 2.9530(12) 2_556 ?
I5 Sb2 3.2066(9) . ?
I6 Sb2 2.8109(11) . ?
I7 Sb2 2.8761(9) . ?
I8 Sb2 2.8995(8) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C0AA 1.521(6) . ?
C0AA C1 1.513(8) . ?
C0AA C2 1.500(9) . ?
C0AA C4 1.521(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N2 H2F 0.8900 . ?
N2 C5 1.514(7) . ?
C5 C6 1.541(10) . ?
C5 C7 1.510(9) . ?
C5 C8 1.502(10) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O1 H1D 0.8503 . ?
O1 H1E 0.8500 . ?

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
Sb1 I3 Sb2 96.79(3) . . ?
Sb1 I4 Sb1 88.86(3) 2_556 . ?
Sb2 I4 Sb1 87.07(2) . 2_556 ?
Sb2 I4 Sb1 90.13(3) . . ?
Sb1 I5 Sb2 96.85(3) 2_556 . ?
I1 Sb1 I2 90.21(3) . . ?
I1 Sb1 I3 92.02(3) . . ?
I1 Sb1 I4 89.96(3) . . ?
I1 Sb1 I5 91.94(3) . 2_556 ?
I2 Sb1 I3 90.01(3) . . ?
I2 Sb1 I4 176.934(14) . . ?
I2 Sb1 I5 93.35(3) . 2_556 ?
I3 Sb1 I4 86.92(3) . . ?
I5 Sb1 I3 174.793(14) 2_556 . ?
I5 Sb1 I4 89.70(3) 2_556 . ?
I3 Sb2 I4 86.14(3) . . ?
I5 Sb2 I3 87.18(3) . . ?
I5 Sb2 I4 86.11(2) . . ?
I6 Sb2 I3 89.40(3) . . ?
I6 Sb2 I4 171.272(16) . . ?
I6 Sb2 I5 86.18(3) . . ?
I6 Sb2 I7 94.57(3) . . ?
I6 Sb2 I8 94.89(3) . . ?
I7 Sb2 I3 176.012(14) . . ?
I7 Sb2 I4 89.97(3) . . ?
I7 Sb2 I5 93.45(3) . . ?
I7 Sb2 I8 89.97(3) . . ?
I8 Sb2 I3 89.32(3) . . ?
I8 Sb2 I4 92.55(3) . . ?
I8 Sb2 I5 176.324(14) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C0AA N3 H3A 109.5 . . ?
C0AA N3 H3B 109.5 . . ?
C0AA N3 H3C 109.5 . . ?
C1 C0AA N3 106.5(5) . . ?
C1 C0AA C4 111.5(5) . . ?
C2 C0AA N3 106.7(5) . . ?
C2 C0AA C1 114.1(6) . . ?
C2 C0AA C4 110.9(6) . . ?
C4 C0AA N3 106.7(4) . . ?
C0AA C1 H1A 109.5 . . ?
C0AA C1 H1B 109.5 . . ?
C0AA C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C0AA C2 H2A 109.5 . . ?
C0AA C2 H2B 109.5 . . ?
C0AA C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C0AA C4 H4A 109.5 . . ?
C0AA C4 H4B 109.5 . . ?
C0AA C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
H2D N2 H2E 109.5 . . ?
H2D N2 H2F 109.5 . . ?
H2E N2 H2F 109.5 . . ?
C5 N2 H2D 109.5 . . ?
C5 N2 H2E 109.5 . . ?
C5 N2 H2F 109.5 . . ?
N2 C5 C6 105.4(6) . . ?
C7 C5 N2 107.3(5) . . ?
C7 C5 C6 110.7(6) . . ?
C8 C5 N2 106.7(5) . . ?
C8 C5 C6 112.3(6) . . ?
C8 C5 C7 113.7(7) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H1D O1 H1E 104.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
