# 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 2023

####################################################################### 
# 
# 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(C4H5N2S-SN2C4H6)]I3I5
_database_code_depnum_ccdc_archive 'CCDC 2242744'
loop_
_audit_author_name
_audit_author_address
'Francesco Demartin' 'Universita degli Studi di Milano'
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 I8 N8 S4'
_chemical_formula_weight         1469.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0461(9)
_cell_length_b                   11.5109(14)
_cell_length_c                   23.868(3)
_cell_angle_alpha                91.440(10)
_cell_angle_beta                 92.780(10)
_cell_angle_gamma                102.417(10)
_cell_volume                     1887.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.04

_exptl_crystal_description       pseudoprism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.587
_exptl_crystal_F_000             1324
_exptl_transmission_factor_min   0.513
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    6.817
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17105
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         26.069
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7423
_reflns_number_gt                4776
_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       'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Diamond - Crystal Impact GbR'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7423
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_restrained_S_all      0.902
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.12010(8) 0.56315(5) 0.40471(2) 0.06528(16) Uani 1 1 d . . . . .
I2 I -0.08899(7) 0.74245(4) 0.44545(2) 0.05310(14) Uani 1 1 d . . . . .
I3 I -0.30039(9) 0.91528(5) 0.48579(3) 0.07990(19) Uani 1 1 d . . . . .
I4 I 0.82683(10) 0.58495(6) 0.01902(3) 0.0825(2) Uani 1 1 d . . . . .
I5 I 0.59723(8) 0.75144(5) 0.03563(2) 0.06425(16) Uani 1 1 d . . . . .
I6 I 0.31983(9) 0.92510(5) 0.05243(2) 0.06731(17) Uani 1 1 d . . . . .
I7 I 0.13644(7) 0.81076(4) 0.15494(2) 0.05137(14) Uani 1 1 d . . . . .
I8 I -0.00474(9) 0.71515(6) 0.25658(3) 0.07816(19) Uani 1 1 d . . . . .
S11 S 0.3970(3) 1.04640(17) 0.78918(8) 0.0529(5) Uani 1 1 d . . . . .
S12 S 0.3715(3) 0.52166(16) 0.67746(7) 0.0539(5) Uani 1 1 d . . . . .
S21 S 0.1120(3) 0.95402(18) 0.76899(8) 0.0537(5) Uani 1 1 d . . . . .
S22 S 0.6491(3) 0.59058(18) 0.71464(7) 0.0526(5) Uani 1 1 d . . . . .
N11 N 0.6007(8) 0.9295(5) 0.7207(2) 0.0526(15) Uani 1 1 d . . . . .
H11 H 0.605295 0.873426 0.743538 0.063 Uiso 1 1 calc R U . . .
N12 N 0.2191(8) 0.7194(6) 0.6632(2) 0.0543(16) Uani 1 1 d . . . . .
H12 H 0.178317 0.719567 0.696598 0.065 Uiso 1 1 calc R U . . .
N21 N 0.5390(8) 1.0865(5) 0.6844(3) 0.0539(15) Uani 1 1 d . . . . .
N22 N 0.3516(8) 0.6706(5) 0.5895(2) 0.0469(14) Uani 1 1 d . . . . .
N31 N 0.1058(8) 0.7169(6) 0.7703(2) 0.0524(15) Uani 1 1 d . . . . .
N32 N 0.6006(8) 0.7553(5) 0.7938(2) 0.0514(15) Uani 1 1 d . . . . .
N41 N 0.0781(8) 0.7950(6) 0.8535(2) 0.0531(15) Uani 1 1 d . . . . .
N42 N 0.5678(8) 0.5727(5) 0.8258(2) 0.0518(15) Uani 1 1 d . . . . .
C11 C 0.5152(9) 1.0190(6) 0.7296(3) 0.0429(16) Uani 1 1 d . . . . .
C12 C 0.3175(9) 0.6443(6) 0.6431(3) 0.0402(15) Uani 1 1 d . . . . .
C21 C 0.6437(11) 1.0393(8) 0.6474(3) 0.065(2) Uani 1 1 d . . . . .
H21 H 0.682842 1.069515 0.612987 0.079 Uiso 1 1 calc R U . . .
C22 C 0.2740(11) 0.7662(7) 0.5769(3) 0.060(2) Uani 1 1 d . . . . .
H22 H 0.277389 0.803380 0.542674 0.072 Uiso 1 1 calc R U . . .
C31 C 0.6799(10) 0.9397(8) 0.6702(3) 0.063(2) Uani 1 1 d . . . . .
H31 H 0.747379 0.887475 0.654087 0.075 Uiso 1 1 calc R U . . .
C32 C 0.1920(10) 0.7964(7) 0.6231(4) 0.062(2) Uani 1 1 d . . . . .
H32 H 0.128206 0.858775 0.626946 0.074 Uiso 1 1 calc R U . . .
C41 C 0.4690(13) 1.1959(8) 0.6768(4) 0.081(3) Uani 1 1 d . . . . .
H41A H 0.329619 1.177075 0.671641 0.098 Uiso 1 1 calc R U . . .
H41B H 0.523968 1.234866 0.644379 0.098 Uiso 1 1 calc R U . . .
H41C H 0.507284 1.247827 0.709394 0.098 Uiso 1 1 calc R U . . .
C42 C 0.4537(12) 0.6037(8) 0.5509(3) 0.072(2) Uani 1 1 d . . . . .
H42A H 0.498054 0.542394 0.570912 0.086 Uiso 1 1 calc R U . . .
H42B H 0.563098 0.657336 0.536691 0.086 Uiso 1 1 calc R U . . .
H42C H 0.365501 0.568294 0.520143 0.086 Uiso 1 1 calc R U . . .
C51 C 0.1044(9) 0.8159(6) 0.7989(3) 0.0437(16) Uani 1 1 d . . . . .
C52 C 0.5995(9) 0.6433(6) 0.7809(3) 0.0437(16) Uani 1 1 d . . . . .
C61 C 0.0801(11) 0.6300(8) 0.8083(4) 0.067(2) Uani 1 1 d . . . . .
H61 H 0.073048 0.549672 0.800213 0.080 Uiso 1 1 calc R U . . .
C62 C 0.5701(10) 0.7577(8) 0.8497(3) 0.063(2) Uani 1 1 d . . . . .
H62 H 0.564199 0.825266 0.871165 0.076 Uiso 1 1 calc R U . . .
C71 C 0.0664(10) 0.6781(8) 0.8593(4) 0.062(2) Uani 1 1 d . . . . .
H71 H 0.051493 0.637745 0.892651 0.075 Uiso 1 1 calc R U . . .
C72 C 0.5500(11) 0.6478(9) 0.8690(3) 0.065(2) Uani 1 1 d . . . . .
H72 H 0.527665 0.626480 0.905779 0.077 Uiso 1 1 calc R U . . .
C81 C 0.0736(13) 0.8829(8) 0.8993(3) 0.080(3) Uani 1 1 d . . . . .
H81A H 0.048540 0.842550 0.933777 0.095 Uiso 1 1 calc R U . . .
H81B H -0.027561 0.924773 0.890628 0.095 Uiso 1 1 calc R U . . .
H81C H 0.196724 0.938457 0.903269 0.095 Uiso 1 1 calc R U . . .
C82 C 0.5586(14) 0.4458(8) 0.8273(4) 0.083(3) Uani 1 1 d . . . . .
H82A H 0.686343 0.430889 0.823471 0.099 Uiso 1 1 calc R U . . .
H82B H 0.472732 0.405625 0.797069 0.099 Uiso 1 1 calc R U . . .
H82C H 0.510629 0.416769 0.862449 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9532(8) . ?
I2 I3 2.9019(8) . ?
I4 I5 2.7936(9) . ?
I5 I6 3.1134(9) . ?
I6 I7 3.0207(8) . ?
I7 I8 2.8255(8) . ?
S11 C11 1.739(7) . ?
S11 S21 2.088(3) . ?
S12 C12 1.752(7) . ?
S12 S22 2.091(3) . ?
S21 C51 1.750(7) . ?
S22 C52 1.758(7) . ?
N11 C11 1.317(8) . ?
N11 C31 1.350(9) . ?
N12 C12 1.314(8) . ?
N12 C32 1.355(9) . ?
N21 C11 1.341(8) . ?
N21 C21 1.354(10) . ?
N21 C41 1.461(10) . ?
N22 C12 1.342(8) . ?
N22 C22 1.364(9) . ?
N22 C42 1.493(9) . ?
N31 C51 1.317(8) . ?
N31 C61 1.357(10) . ?
N32 C52 1.316(9) . ?
N32 C62 1.362(9) . ?
N41 C71 1.341(10) . ?
N41 C51 1.346(8) . ?
N41 C81 1.476(10) . ?
N42 C72 1.356(9) . ?
N42 C52 1.359(8) . ?
N42 C82 1.450(10) . ?
C21 C31 1.350(11) . ?
C22 C32 1.343(10) . ?
C61 C71 1.342(11) . ?
C62 C72 1.338(11) . ?

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
I3 I2 I1 178.98(2) . . ?
I4 I5 I6 176.63(3) . . ?
I7 I6 I5 96.26(2) . . ?
I8 I7 I6 174.79(2) . . ?
C11 S11 S21 102.0(2) . . ?
C12 S12 S22 102.6(2) . . ?
C51 S21 S11 103.0(2) . . ?
C52 S22 S12 103.0(2) . . ?
C11 N11 C31 109.3(6) . . ?
C12 N12 C32 109.3(6) . . ?
C11 N21 C21 109.3(7) . . ?
C11 N21 C41 125.7(6) . . ?
C21 N21 C41 125.0(7) . . ?
C12 N22 C22 108.3(6) . . ?
C12 N22 C42 125.0(6) . . ?
C22 N22 C42 126.7(6) . . ?
C51 N31 C61 105.5(6) . . ?
C52 N32 C62 104.9(6) . . ?
C71 N41 C51 106.5(6) . . ?
C71 N41 C81 125.9(7) . . ?
C51 N41 C81 127.5(7) . . ?
C72 N42 C52 104.6(6) . . ?
C72 N42 C82 127.7(7) . . ?
C52 N42 C82 127.7(6) . . ?
N11 C11 N21 107.3(6) . . ?
N11 C11 S11 126.5(5) . . ?
N21 C11 S11 126.1(6) . . ?
N12 C12 N22 107.9(6) . . ?
N12 C12 S12 126.0(5) . . ?
N22 C12 S12 125.7(5) . . ?
C31 C21 N21 106.3(7) . . ?
C32 C22 N22 107.0(7) . . ?
C21 C31 N11 107.7(7) . . ?
C22 C32 N12 107.4(7) . . ?
N31 C51 N41 111.1(6) . . ?
N31 C51 S21 124.5(5) . . ?
N41 C51 S21 124.2(6) . . ?
N32 C52 N42 112.5(6) . . ?
N32 C52 S22 124.5(5) . . ?
N42 C52 S22 122.9(6) . . ?
C71 C61 N31 109.3(7) . . ?
C72 C62 N32 109.5(7) . . ?
N41 C71 C61 107.5(7) . . ?
C62 C72 N42 108.6(7) . . ?

_refine_diff_density_max         1.177
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.146



