# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_25GPa
_database_code_depnum_ccdc_archive 'CCDC 2466417'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I5 N2 S2'
_chemical_formula_weight         1007.99

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.1949(6)
_cell_length_b                   10.1933(2)
_cell_length_c                   17.920(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.678(14)
_cell_angle_gamma                90
_cell_volume                     2360.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3164
_cell_measurement_theta_min      2.5310
_cell_measurement_theta_max      27.5540

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.837
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    6.771
_exptl_absorpt_correction_T_min  0.03427
_exptl_absorpt_correction_T_max  0.05791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.809
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            13048
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         28.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.320
_diffrn_measured_fraction_theta_full 0.359
_diffrn_reflns_Laue_measured_fraction_max 0.320
_diffrn_reflns_Laue_measured_fraction_full 0.359
_diffrn_reflns_point_group_measured_fraction_max 0.320
_diffrn_reflns_point_group_measured_fraction_full 0.359
_reflns_number_total             13048
_reflns_number_gt                8842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1556P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13048
_refine_ls_number_parameters     83
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_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 0.59253(15) 0.29138(15) 0.4773(3) 0.087(4) Uani 1 1 d . U . . .
C4 C 0.202(3) 0.674(2) 0.698(5) 0.080(9) Uani 1 1 d . U . . .
H4 H 0.133780 0.702908 0.693115 0.096 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.0080(2) 0.750000 0.084(5) Uani 1 2 d S TU P . .
I3 I 0.33469(17) -0.01164(17) 0.6172(3) 0.089(4) Uani 1 1 d . U . . .
C9 C 0.223(2) 0.558(2) 0.655(5) 0.080(9) Uani 1 1 d . U . . .
S1 S 0.4768(6) 0.3376(7) 0.6483(13) 0.096(11) Uani 1 1 d . U . . .
C11 C 0.547(3) 0.456(3) 0.599(5) 0.080(9) Uani 1 1 d . U . . .
H11A H 0.533044 0.542739 0.615950 0.096 Uiso 1 1 calc R U . . .
H11B H 0.620609 0.439746 0.616888 0.096 Uiso 1 1 calc R U . . .
C12 C 0.530(3) 0.458(3) 0.525(5) 0.080(9) Uani 1 1 d . U . . .
N1 N 0.4007(18) 0.5778(18) 0.730(3) 0.081(18) Uani 1 1 d D U . . .
H1 H 0.500000 0.535(17) 0.750000 0.097 Uiso 1 2 d DS U P . .
C5 C 0.145(2) 0.491(2) 0.595(5) 0.080(9) Uani 1 1 d . U . . .
H5 H 0.078669 0.524116 0.581846 0.096 Uiso 1 1 calc R U . . .
C10 C 0.328(3) 0.517(2) 0.671(5) 0.080(9) Uani 1 1 d . U . . .
C6 C 0.169(2) 0.387(3) 0.561(5) 0.080(9) Uani 1 1 d . U . . .
H6 H 0.120682 0.344237 0.524363 0.096 Uiso 1 1 calc R U . . .
C7 C 0.276(2) 0.338(3) 0.583(5) 0.080(9) Uani 1 1 d . U . . .
H7 H 0.291051 0.256656 0.564853 0.096 Uiso 1 1 calc R U . . .
C2 C 0.375(3) 0.684(2) 0.754(5) 0.080(9) Uani 1 1 d . U . . .
H2 H 0.426645 0.735951 0.782349 0.096 Uiso 1 1 calc R U . . .
C8 C 0.350(2) 0.401(3) 0.627(5) 0.080(9) Uani 1 1 d . U . . .
C3 C 0.272(2) 0.734(2) 0.741(4) 0.080(9) Uani 1 1 d . U . . .
H3 H 0.258256 0.811314 0.764275 0.096 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 C12 2.14(4) . ?
C4 C3 1.24(7) . ?
C4 C9 1.47(7) . ?
C4 H4 0.9300 . ?
I2 I3 2.885(5) 2_656 ?
I2 I3 2.885(5) . ?
C9 C10 1.41(4) . ?
C9 C5 1.49(9) . ?
S1 C8 1.76(3) . ?
S1 C11 1.85(5) . ?
C11 C12 1.30(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.37(12) 5_666 ?
N1 C2 1.24(4) . ?
N1 C10 1.43(8) . ?
N1 H1 1.36(5) . ?
C5 C6 1.29(6) . ?
C5 H5 0.9300 . ?
C10 C8 1.48(7) . ?
C6 C7 1.47(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.29(7) . ?
C7 H7 0.9300 . ?
C2 C3 1.42(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C3 C4 C9 121(3) . . ?
C3 C4 H4 119.4 . . ?
C9 C4 H4 119.4 . . ?
I3 I2 I3 178.55(11) 2_656 . ?
C10 C9 C4 115(5) . . ?
C10 C9 C5 121(4) . . ?
C4 C9 C5 125(3) . . ?
C8 S1 C11 102(2) . . ?
C12 C11 S1 120(4) . . ?
C12 C11 H11A 107.4 . . ?
S1 C11 H11A 107.4 . . ?
C12 C11 H11B 107.4 . . ?
S1 C11 H11B 107.4 . . ?
H11A C11 H11B 106.9 . . ?
C12 C12 C11 129(6) 5_666 . ?
C12 C12 I1 117(7) 5_666 . ?
C11 C12 I1 113(3) . . ?
C2 N1 C10 116(4) . . ?
C2 N1 H1 121(8) . . ?
C10 N1 H1 122(6) . . ?
C6 C5 C9 121(3) . . ?
C6 C5 H5 119.4 . . ?
C9 C5 H5 119.4 . . ?
C9 C10 N1 120(5) . . ?
C9 C10 C8 115(5) . . ?
N1 C10 C8 125(3) . . ?
C5 C6 C7 118(5) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C8 C7 C6 124(4) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
N1 C2 C3 125(5) . . ?
N1 C2 H2 117.4 . . ?
C3 C2 H2 117.4 . . ?
C7 C8 C10 121(3) . . ?
C7 C8 S1 121(3) . . ?
C10 C8 S1 117(4) . . ?
C4 C3 C2 120(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?

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
C3 C4 C9 C10 5(9) . . . . ?
C3 C4 C9 C5 -172(6) . . . . ?
C8 S1 C11 C12 -70(4) . . . . ?
S1 C11 C12 C12 101(5) . . . 5_666 ?
S1 C11 C12 I1 -72(3) . . . . ?
C10 C9 C5 C6 6(9) . . . . ?
C4 C9 C5 C6 -178(6) . . . . ?
C4 C9 C10 N1 6(8) . . . . ?
C5 C9 C10 N1 -177(5) . . . . ?
C4 C9 C10 C8 -179(5) . . . . ?
C5 C9 C10 C8 -3(8) . . . . ?
C2 N1 C10 C9 -16(8) . . . . ?
C2 N1 C10 C8 170(5) . . . . ?
C9 C5 C6 C7 -1(9) . . . . ?
C5 C6 C7 C8 -9(10) . . . . ?
C10 N1 C2 C3 16(9) . . . . ?
C6 C7 C8 C10 13(10) . . . . ?
C6 C7 C8 S1 -178(5) . . . . ?
C9 C10 C8 C7 -7(9) . . . . ?
N1 C10 C8 C7 168(6) . . . . ?
C9 C10 C8 S1 -176(5) . . . . ?
N1 C10 C8 S1 -1(8) . . . . ?
C11 S1 C8 C7 113(6) . . . . ?
C11 S1 C8 C10 -78(5) . . . . ?
C9 C4 C3 C2 -6(9) . . . . ?
N1 C2 C3 C4 -6(10) . . . . ?

_refine_diff_density_max         1.622
_refine_diff_density_min         -1.880
_refine_diff_density_rms         0.438

####################################################################### 
# 
# 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_327GPa
_database_code_depnum_ccdc_archive 'CCDC 2466418'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I5 N2 S2'
_chemical_formula_weight         1007.99

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.1052(9)
_cell_length_b                   10.1023(3)
_cell_length_c                   17.643(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.00(2)
_cell_angle_gamma                90
_cell_volume                     2284.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      2.5580
_cell_measurement_theta_max      26.9450

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.930
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    7.006
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.778
_oxdiff_exptl_absorpt_empirical_full_max 1.877
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            11997
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         27.970
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.331
_diffrn_measured_fraction_theta_full 0.361
_diffrn_reflns_Laue_measured_fraction_max 0.331
_diffrn_reflns_Laue_measured_fraction_full 0.361
_diffrn_reflns_point_group_measured_fraction_max 0.331
_diffrn_reflns_point_group_measured_fraction_full 0.361
_reflns_number_total             11997
_reflns_number_gt                7883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1760P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11997
_refine_ls_number_parameters     83
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.1922
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002

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 0.59495(16) 0.29163(16) 0.4762(3) 0.088(4) Uani 1 1 d . . . . .
C4 C 0.201(3) 0.677(3) 0.693(5) 0.057(12) Uani 1 1 d . U . . .
H4 H 0.135004 0.714161 0.681421 0.068 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.0089(2) 0.750000 0.085(6) Uani 1 2 d S T P . .
I3 I 0.33059(19) -0.01219(18) 0.6170(4) 0.087(5) Uani 1 1 d . . . . .
C9 C 0.220(3) 0.560(3) 0.655(5) 0.057(12) Uani 1 1 d . U . . .
S1 S 0.4719(7) 0.3310(7) 0.6451(15) 0.109(14) Uani 1 1 d . . . . .
C11 C 0.546(3) 0.451(3) 0.599(6) 0.057(12) Uani 1 1 d . U . . .
H11A H 0.533059 0.538647 0.617932 0.068 Uiso 1 1 calc R U . . .
H11B H 0.619639 0.432804 0.617590 0.068 Uiso 1 1 calc R U . . .
C12 C 0.529(3) 0.457(3) 0.526(5) 0.057(12) Uani 1 1 d . U . . .
N1 N 0.399(2) 0.5762(19) 0.732(4) 0.05(4) Uani 1 1 d D . . . .
H1 H 0.500000 0.534(17) 0.750000 0.066 Uiso 1 2 d DS U P . .
C5 C 0.142(3) 0.489(2) 0.600(6) 0.057(12) Uani 1 1 d . U . . .
H5 H 0.072755 0.516045 0.593358 0.068 Uiso 1 1 calc R U . . .
C10 C 0.323(3) 0.515(3) 0.666(6) 0.057(12) Uani 1 1 d . U . . .
C6 C 0.164(3) 0.386(3) 0.559(5) 0.057(12) Uani 1 1 d . U . . .
H6 H 0.115240 0.349787 0.518544 0.068 Uiso 1 1 calc R U . . .
C7 C 0.273(3) 0.334(3) 0.584(5) 0.057(12) Uani 1 1 d . U . . .
H7 H 0.288479 0.250184 0.566928 0.068 Uiso 1 1 calc R U . . .
C2 C 0.374(3) 0.682(3) 0.755(6) 0.057(12) Uani 1 1 d . U . . .
H2 H 0.428367 0.732919 0.783623 0.068 Uiso 1 1 calc R U . . .
C8 C 0.346(3) 0.400(3) 0.627(5) 0.057(12) Uani 1 1 d . U . . .
C3 C 0.277(2) 0.736(3) 0.744(5) 0.057(12) Uani 1 1 d . U . . .
H3 H 0.263513 0.810378 0.771744 0.068 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 C12 2.15(4) . ?
C4 C3 1.34(8) . ?
C4 C9 1.39(7) . ?
C4 H4 0.9300 . ?
I2 I3 2.876(5) 2_656 ?
I2 I3 2.876(5) . ?
C9 C10 1.40(4) . ?
C9 C5 1.45(9) . ?
S1 C8 1.76(3) . ?
S1 C11 1.85(5) . ?
C11 C12 1.27(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.37(12) 5_666 ?
N1 C2 1.22(5) . ?
N1 C10 1.50(9) . ?
N1 H1 1.36(5) . ?
C5 C6 1.33(7) . ?
C5 H5 0.9300 . ?
C10 C8 1.42(7) . ?
C6 C7 1.51(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.28(8) . ?
C7 H7 0.9300 . ?
C2 C3 1.36(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C3 C4 C9 121(3) . . ?
C3 C4 H4 119.3 . . ?
C9 C4 H4 119.3 . . ?
I3 I2 I3 178.67(11) 2_656 . ?
C4 C9 C10 118(5) . . ?
C4 C9 C5 125(3) . . ?
C10 C9 C5 117(5) . . ?
C8 S1 C11 103(2) . . ?
C12 C11 S1 119(5) . . ?
C12 C11 H11A 107.6 . . ?
S1 C11 H11A 107.6 . . ?
C12 C11 H11B 107.6 . . ?
S1 C11 H11B 107.6 . . ?
H11A C11 H11B 107.0 . . ?
C11 C12 C12 132(7) . 5_666 ?
C11 C12 I1 112(4) . . ?
C12 C12 I1 116(7) 5_666 . ?
C2 N1 C10 116(4) . . ?
C2 N1 H1 121(8) . . ?
C10 N1 H1 121(6) . . ?
C6 C5 C9 124(3) . . ?
C6 C5 H5 118.3 . . ?
C9 C5 H5 118.2 . . ?
C9 C10 C8 120(5) . . ?
C9 C10 N1 116(5) . . ?
C8 C10 N1 123(3) . . ?
C5 C6 C7 115(6) . . ?
C5 C6 H6 122.7 . . ?
C7 C6 H6 122.7 . . ?
C8 C7 C6 122(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
N1 C2 C3 128(5) . . ?
N1 C2 H2 116.2 . . ?
C3 C2 H2 116.2 . . ?
C7 C8 C10 121(3) . . ?
C7 C8 S1 117(3) . . ?
C10 C8 S1 122(4) . . ?
C4 C3 C2 117(5) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?

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
C3 C4 C9 C10 -7(10) . . . . ?
C3 C4 C9 C5 178(6) . . . . ?
C8 S1 C11 C12 -72(5) . . . . ?
S1 C11 C12 C12 101(6) . . . 5_666 ?
S1 C11 C12 I1 -74(4) . . . . ?
C4 C9 C5 C6 173(6) . . . . ?
C10 C9 C5 C6 -2(10) . . . . ?
C4 C9 C10 C8 -178(6) . . . . ?
C5 C9 C10 C8 -3(10) . . . . ?
C4 C9 C10 N1 15(9) . . . . ?
C5 C9 C10 N1 -171(5) . . . . ?
C2 N1 C10 C9 -20(8) . . . . ?
C2 N1 C10 C8 172(5) . . . . ?
C9 C5 C6 C7 10(9) . . . . ?
C5 C6 C7 C8 -16(9) . . . . ?
C10 N1 C2 C3 19(11) . . . . ?
C6 C7 C8 C10 12(11) . . . . ?
C6 C7 C8 S1 -175(5) . . . . ?
C9 C10 C8 C7 -2(11) . . . . ?
N1 C10 C8 C7 164(6) . . . . ?
C9 C10 C8 S1 -175(6) . . . . ?
N1 C10 C8 S1 -8(9) . . . . ?
C11 S1 C8 C7 116(6) . . . . ?
C11 S1 C8 C10 -72(6) . . . . ?
C9 C4 C3 C2 4(10) . . . . ?
N1 C2 C3 C4 -11(11) . . . . ?

_refine_diff_density_max         1.583
_refine_diff_density_min         -1.998
_refine_diff_density_rms         0.438

####################################################################### 
# 
# 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_2GPa
_database_code_depnum_ccdc_archive 'CCDC 2466421'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I5 N2 S2'
_chemical_formula_weight         1007.99

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.2397(8)
_cell_length_b                   10.2700(3)
_cell_length_c                   18.056(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.603(19)
_cell_angle_gamma                90
_cell_volume                     2405.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1368
_cell_measurement_theta_min      3.1250
_cell_measurement_theta_max      26.4830

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.784
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.656
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.03642
_exptl_absorpt_correction_T_max  0.05975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.600
_oxdiff_exptl_absorpt_empirical_full_max 2.198
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            7347
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         28.189
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.309
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.309
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.309
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             914
_reflns_number_gt                746
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0629P)²+14.0239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         914
_refine_ls_number_parameters     127
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.089
_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
I1 I 0.59085(7) 0.29183(8) 0.47760(14) 0.0535(19) Uani 1 1 d . U . . .
C4 C 0.2006(11) 0.6733(11) 0.695(2) 0.046(3) Uiso 1 1 d . U . . .
H4 H 0.132688 0.701743 0.687673 0.055 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.00775(10) 0.750000 0.054(2) Uani 1 2 d S TU P . .
I3 I 0.33757(8) -0.01181(9) 0.61654(17) 0.065(2) Uani 1 1 d . U . . .
C9 C 0.2242(11) 0.5610(12) 0.653(2) 0.051(8) Uani 1 1 d . U . . .
S1 S 0.4808(3) 0.3420(3) 0.6510(6) 0.050(5) Uani 1 1 d . U . . .
C11 C 0.550(2) 0.460(2) 0.597(3) 0.049(9) Uani 1 1 d . U . . .
H11A H 0.536343 0.547292 0.612768 0.059 Uiso 1 1 calc R U . . .
H11B H 0.623335 0.444726 0.613002 0.059 Uiso 1 1 calc R U . . .
C12 C 0.529(2) 0.4571(17) 0.525(3) 0.044(10) Uani 1 1 d . U . . .
N1 N 0.3974(7) 0.5786(9) 0.7225(15) 0.046(9) Uani 1 1 d D U . . .
H1 H 0.500000 0.586(15) 0.750000 0.055 Uiso 1 2 d DS U P . .
C5 C 0.1493(13) 0.4897(15) 0.599(3) 0.065(10) Uani 1 1 d . U . . .
H5 H 0.081262 0.518200 0.588591 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3256(11) 0.5162(10) 0.668(2) 0.047(8) Uani 1 1 d . U . . .
C6 C 0.1748(15) 0.3854(17) 0.566(3) 0.067(10) Uani 1 1 d . U . . .
H6 H 0.125212 0.340748 0.530977 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2812(14) 0.3396(15) 0.582(2) 0.060(10) Uani 1 1 d . U . . .
H7 H 0.298284 0.262058 0.561268 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3737(12) 0.6845(12) 0.754(2) 0.052(9) Uani 1 1 d . U . . .
H2 H 0.425133 0.730035 0.786812 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3533(11) 0.4070(12) 0.627(2) 0.048(3) Uiso 1 1 d . U . . .
C3 C 0.2688(11) 0.7336(13) 0.740(2) 0.055(3) Uiso 1 1 d . U . . .
H3 H 0.252330 0.808167 0.764520 0.066 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 C12 2.14(2) . ?
C4 C3 1.25(4) . ?
C4 C9 1.45(3) . ?
C4 H4 0.9300 . ?
I2 I3 2.889(3) 2_656 ?
I2 I3 2.889(3) . ?
C9 C10 1.39(2) . ?
C9 C5 1.44(4) . ?
S1 C8 1.785(16) . ?
S1 C11 1.90(3) . ?
C11 C12 1.27(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.37(8) 5_666 ?
N1 C2 1.30(2) . ?
N1 C10 1.38(3) . ?
N1 H1 1.351(12) . ?
C5 C6 1.31(4) . ?
C5 H5 0.9300 . ?
C10 C8 1.43(3) . ?
C6 C7 1.46(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.32(4) . ?
C7 H7 0.9300 . ?
C2 C3 1.45(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C3 C4 C9 122.2(14) . . ?
C3 C4 H4 118.9 . . ?
C9 C4 H4 118.9 . . ?
I3 I2 I3 178.35(5) 2_656 . ?
C10 C9 C5 118.3(19) . . ?
C10 C9 C4 117(2) . . ?
C5 C9 C4 124.4(14) . . ?
C8 S1 C11 99.6(13) . . ?
C12 C11 S1 119(3) . . ?
C12 C11 H11A 107.7 . . ?
S1 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
S1 C11 H11B 107.7 . . ?
H11A C11 H11B 107.1 . . ?
C11 C12 C12 130(4) . 5_666 ?
C11 C12 I1 114(3) . . ?
C12 C12 I1 117(5) 5_666 . ?
C2 N1 C10 120.7(14) . . ?
C2 N1 H1 96(6) . . ?
C10 N1 H1 142(5) . . ?
C6 C5 C9 121.5(18) . . ?
C6 C5 H5 119.3 . . ?
C9 C5 H5 119.3 . . ?
N1 C10 C9 119.3(19) . . ?
N1 C10 C8 121.4(13) . . ?
C9 C10 C8 119(2) . . ?
C5 C6 C7 120(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N1 C2 C3 121(2) . . ?
N1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C7 C8 C10 120.0(14) . . ?
C7 C8 S1 119.1(13) . . ?
C10 C8 S1 120(2) . . ?
C4 C3 C2 119(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?

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
C3 C4 C9 C10 4(4) . . . . ?
C3 C4 C9 C5 -179(3) . . . . ?
S1 C11 C12 C12 106(3) . . . 5_666 ?
S1 C11 C12 I1 -74(3) . . . . ?
C10 C9 C5 C6 0(5) . . . . ?
C4 C9 C5 C6 -177(3) . . . . ?
C2 N1 C10 C9 -6(4) . . . . ?
C2 N1 C10 C8 173(3) . . . . ?
C5 C9 C10 N1 -176(3) . . . . ?
C4 C9 C10 N1 1(4) . . . . ?
C5 C9 C10 C8 4(4) . . . . ?
C4 C9 C10 C8 -179(2) . . . . ?
C9 C5 C6 C7 0(5) . . . . ?
C5 C6 C7 C8 -5(5) . . . . ?
C10 N1 C2 C3 7(4) . . . . ?
C6 C7 C8 C10 9(5) . . . . ?
C6 C7 C8 S1 176(3) . . . . ?
N1 C10 C8 C7 172(3) . . . . ?
C9 C10 C8 C7 -9(4) . . . . ?
N1 C10 C8 S1 5(3) . . . . ?
C9 C10 C8 S1 -176(2) . . . . ?
C11 S1 C8 C7 111(3) . . . . ?
C11 S1 C8 C10 -82(3) . . . . ?
C9 C4 C3 C2 -3(4) . . . . ?
N1 C2 C3 C4 -2(5) . . . . ?

_refine_diff_density_max         0.807
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.140

####################################################################### 
# 
# 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_052GPa
_database_code_depnum_ccdc_archive 'CCDC 2466419'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 I5 N2 S2'
_chemical_formula_weight         1009.00

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.3167(3)
_cell_length_b                   11.0072(2)
_cell_length_c                   18.382(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.320(9)
_cell_angle_gamma                90
_cell_volume                     2666.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3552
_cell_measurement_theta_min      2.4070
_cell_measurement_theta_max      27.0680

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.514
_exptl_crystal_F_000             1844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.004
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.76302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.795
_oxdiff_exptl_absorpt_empirical_full_max 1.257
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            8330
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.868
_diffrn_reflns_theta_max         28.046
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.318
_diffrn_measured_fraction_theta_full 0.357
_diffrn_reflns_Laue_measured_fraction_max 0.318
_diffrn_reflns_Laue_measured_fraction_full 0.357
_diffrn_reflns_point_group_measured_fraction_max 0.318
_diffrn_reflns_point_group_measured_fraction_full 0.357
_reflns_number_total             1031
_reflns_number_gt                859
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0394P)²+19.8186P] 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         1031
_refine_ls_number_parameters     141
_refine_ls_number_restraints     119
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.821
_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
I1 I 0.57344(5) 0.29304(5) 0.47944(9) 0.0674(11) Uani 1 1 d . U . . .
C1 C 0.2011(6) 0.6509(7) 0.6753(12) 0.063(7) Uani 1 1 d . U . . .
H1 H 0.133271 0.670592 0.660721 0.076 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.00368(6) 0.750000 0.0703(14) Uani 1 2 d S TU P . .
I3 I 0.37117(5) -0.00757(5) 0.60786(11) 0.0861(13) Uani 1 1 d . U . . .
C10 C 0.2411(6) 0.5446(7) 0.6481(12) 0.051(7) Uani 1 1 d . U . . .
S1 S 0.52008(16) 0.38240(17) 0.6629(3) 0.058(3) Uani 1 1 d . U . . .
C11 C 0.5735(6) 0.4827(8) 0.6005(16) 0.056(5) Uani 1 1 d . U . . .
H11A H 0.561271 0.566193 0.613580 0.067 Uiso 1 1 calc R U . . .
H11B H 0.646371 0.470460 0.606237 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5315(7) 0.4630(8) 0.5248(15) 0.051(4) Uani 1 1 d . U . . .
N4 N 0.4021(4) 0.5961(5) 0.7175(9) 0.054(6) Uani 1 1 d . U . . .
H4 H 0.465294 0.580243 0.731193 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1812(7) 0.4610(9) 0.6005(14) 0.066(8) Uani 1 1 d . U . . .
H8 H 0.112710 0.476896 0.585618 0.079 Uiso 1 1 calc R U . . .
C9 C 0.3454(6) 0.5197(6) 0.6693(11) 0.049(6) Uani 1 1 d . U . . .
C7 C 0.2223(7) 0.3613(9) 0.5773(14) 0.074(8) Uani 1 1 d . U . . .
H7 H 0.181275 0.305284 0.549158 0.089 Uiso 1 1 calc R U . . .
C6 C 0.3275(7) 0.3386(7) 0.5948(13) 0.061(7) Uani 1 1 d . U . . .
H6 H 0.355594 0.270374 0.575677 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3621(6) 0.6934(6) 0.7434(12) 0.067(7) Uani 1 1 d . U . . .
H3 H 0.402814 0.742775 0.776568 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3885(5) 0.4167(6) 0.6398(11) 0.048(6) Uani 1 1 d . U . . .
C2 C 0.2601(6) 0.7251(6) 0.7227(12) 0.062(7) Uani 1 1 d . U . . .
H2 H 0.233562 0.795128 0.740811 0.074 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 C12 2.154(12) . ?
C1 C2 1.36(2) . ?
C1 C10 1.407(15) . ?
C1 H1 0.9300 . ?
I2 I3 2.9112(19) . ?
I2 I3 2.9112(19) 2_656 ?
C10 C9 1.414(13) . ?
C10 C8 1.43(2) . ?
S1 C5 1.783(8) . ?
S1 C11 1.81(2) . ?
C11 C12 1.44(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.41(4) 5_666 ?
N4 C3 1.316(12) . ?
N4 C9 1.368(18) . ?
N4 H4 0.8600 . ?
C8 C7 1.324(16) . ?
C8 H8 0.9300 . ?
C9 C5 1.413(14) . ?
C7 C6 1.413(14) . ?
C7 H7 0.9300 . ?
C6 C5 1.38(2) . ?
C6 H6 0.9300 . ?
C3 C2 1.400(13) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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
C2 C1 C10 120.9(9) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
I3 I2 I3 178.32(3) . 2_656 ?
C1 C10 C9 118.1(13) . . ?
C1 C10 C8 123.1(9) . . ?
C9 C10 C8 118.8(9) . . ?
C5 S1 C11 100.5(7) . . ?
C12 C11 S1 112.8(8) . . ?
C12 C11 H11A 109.0 . . ?
S1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
S1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C12 C11 130.6(16) 5_666 . ?
C12 C12 I1 115(2) 5_666 . ?
C11 C12 I1 114.8(10) . . ?
C3 N4 C9 121.3(8) . . ?
C3 N4 H4 119.3 . . ?
C9 N4 H4 119.3 . . ?
C7 C8 C10 120.7(10) . . ?
C7 C8 H8 119.7 . . ?
C10 C8 H8 119.7 . . ?
N4 C9 C10 119.2(9) . . ?
N4 C9 C5 121.6(8) . . ?
C10 C9 C5 119.2(13) . . ?
C8 C7 C6 121.1(14) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C5 C6 C7 120.4(10) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N4 C3 C2 122.1(13) . . ?
N4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C6 C5 C9 119.7(8) . . ?
C6 C5 S1 119.0(7) . . ?
C9 C5 S1 121.3(11) . . ?
C1 C2 C3 118.3(9) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?

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
C2 C1 C10 C9 -2(2) . . . . ?
C2 C1 C10 C8 177.5(16) . . . . ?
C5 S1 C11 C12 -56.5(9) . . . . ?
S1 C11 C12 C12 111.7(17) . . . 5_666 ?
S1 C11 C12 I1 -69.1(9) . . . . ?
C1 C10 C8 C7 -178.9(19) . . . . ?
C9 C10 C8 C7 1(3) . . . . ?
C3 N4 C9 C10 -1(2) . . . . ?
C3 N4 C9 C5 178.3(15) . . . . ?
C1 C10 C9 N4 3(2) . . . . ?
C8 C10 C9 N4 -177.0(14) . . . . ?
C1 C10 C9 C5 -176.9(15) . . . . ?
C8 C10 C9 C5 3(2) . . . . ?
C10 C8 C7 C6 -4(3) . . . . ?
C8 C7 C6 C5 4(3) . . . . ?
C9 N4 C3 C2 -1(2) . . . . ?
C7 C6 C5 C9 1(3) . . . . ?
C7 C6 C5 S1 178.0(15) . . . . ?
N4 C9 C5 C6 176.3(14) . . . . ?
C10 C9 C5 C6 -4(2) . . . . ?
N4 C9 C5 S1 -1(2) . . . . ?
C10 C9 C5 S1 178.6(12) . . . . ?
C11 S1 C5 C6 101.0(14) . . . . ?
C11 S1 C5 C9 -81.7(16) . . . . ?
C10 C1 C2 C3 0(2) . . . . ?
N4 C3 C2 C1 1(2) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_154GPa
_database_code_depnum_ccdc_archive 'CCDC 2466420'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I5 N2 S2'
_chemical_formula_weight         1007.99

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.1291(4)
_cell_length_b                   10.7512(2)
_cell_length_c                   17.970(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.674(11)
_cell_angle_gamma                90
_cell_volume                     2500.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3541
_cell_measurement_theta_min      2.4530
_cell_measurement_theta_max      27.5870

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.678
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.401
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.836
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            7871
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         28.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.319
_diffrn_measured_fraction_theta_full 0.358
_diffrn_reflns_Laue_measured_fraction_max 0.319
_diffrn_reflns_Laue_measured_fraction_full 0.358
_diffrn_reflns_point_group_measured_fraction_max 0.319
_diffrn_reflns_point_group_measured_fraction_full 0.358
_reflns_number_total             975
_reflns_number_gt                807
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0509P)²+6.3182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         975
_refine_ls_number_parameters     142
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      0.949
_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
I1 I 0.57955(5) 0.29142(5) 0.47972(9) 0.0621(12) Uani 1 1 d . U . . .
C4 C 0.1945(6) 0.6523(7) 0.6748(13) 0.053(8) Uani 1 1 d . U . . .
H4 H 0.124886 0.671277 0.660627 0.063 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.00293(6) 0.750000 0.0687(15) Uani 1 2 d S TU P . .
I3 I 0.36418(5) -0.00882(5) 0.60555(11) 0.0812(14) Uani 1 1 d . U . . .
C9 C 0.2345(6) 0.5423(7) 0.6472(12) 0.048(7) Uani 1 1 d . U . . .
S1 S 0.51858(18) 0.37787(18) 0.6647(4) 0.061(3) Uani 1 1 d . U . . .
C11 C 0.5732(8) 0.4840(9) 0.6013(19) 0.057(5) Uani 1 1 d . U . . .
H11A H 0.558625 0.569133 0.614066 0.069 Uiso 1 1 calc R U . . .
H11B H 0.647638 0.473814 0.609293 0.069 Uiso 1 1 calc R U . . .
C12 C 0.5329(7) 0.4629(9) 0.5238(16) 0.054(5) Uani 1 1 d . U . . .
N1 N 0.4007(4) 0.5973(5) 0.7184(9) 0.052(7) Uani 1 1 d D U . . .
H1 H 0.500000 0.574(7) 0.750000 0.062 Uiso 1 2 d DS U P . .
C5 C 0.1732(7) 0.4568(9) 0.6007(14) 0.064(8) Uani 1 1 d . U . . .
H5 H 0.102858 0.471556 0.586144 0.077 Uiso 1 1 calc R U . . .
C10 C 0.3426(6) 0.5183(6) 0.6709(13) 0.048(6) Uani 1 1 d . U . . .
C6 C 0.2159(8) 0.3536(9) 0.5772(15) 0.065(9) Uani 1 1 d . U . . .
H6 H 0.173936 0.295834 0.548221 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3207(7) 0.3315(8) 0.5951(13) 0.056(8) Uani 1 1 d . U . . .
H7 H 0.348384 0.261003 0.576180 0.067 Uiso 1 1 calc R U . . .
C2 C 0.3595(6) 0.6978(6) 0.7427(13) 0.058(8) Uani 1 1 d . U . . .
H2 H 0.401463 0.750334 0.775778 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3857(6) 0.4130(6) 0.6412(12) 0.051(7) Uani 1 1 d . U . . .
C3 C 0.2553(7) 0.7290(7) 0.7209(13) 0.056(8) Uani 1 1 d . U . . .
H3 H 0.228919 0.801778 0.738213 0.067 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 C12 2.137(12) . ?
C4 C3 1.33(2) . ?
C4 C9 1.417(15) . ?
C4 H4 0.9300 . ?
I2 I3 2.8924(19) 2_656 ?
I2 I3 2.8924(19) . ?
C9 C5 1.40(2) . ?
C9 C10 1.435(13) . ?
S1 C8 1.766(8) . ?
S1 C11 1.84(2) . ?
C11 C12 1.42(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.37(4) 5_666 ?
N1 C2 1.316(12) . ?
N1 C10 1.345(18) . ?
N1 H1 1.355(13) . ?
C5 C6 1.343(16) . ?
C5 H5 0.9300 . ?
C10 C8 1.410(14) . ?
C6 C7 1.379(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.39(2) . ?
C7 H7 0.9300 . ?
C2 C3 1.399(14) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C3 C4 C9 121.0(9) . . ?
C3 C4 H4 119.5 . . ?
C9 C4 H4 119.5 . . ?
I3 I2 I3 177.49(3) 2_656 . ?
C5 C9 C4 123.2(9) . . ?
C5 C9 C10 120.0(9) . . ?
C4 C9 C10 116.8(13) . . ?
C8 S1 C11 101.0(7) . . ?
C12 C11 S1 112.8(9) . . ?
C12 C11 H11A 109.0 . . ?
S1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
S1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C12 C11 127.8(18) 5_666 . ?
C12 C12 I1 117(2) 5_666 . ?
C11 C12 I1 114.7(12) . . ?
C2 N1 C10 120.6(8) . . ?
C2 N1 H1 116(3) . . ?
C10 N1 H1 124(3) . . ?
C6 C5 C9 120.1(10) . . ?
C6 C5 H5 120.0 . . ?
C9 C5 H5 120.0 . . ?
N1 C10 C8 121.7(8) . . ?
N1 C10 C9 120.1(9) . . ?
C8 C10 C9 118.1(14) . . ?
C5 C6 C7 121.5(15) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 121.1(11) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
N1 C2 C3 122.7(13) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C7 C8 C10 119.0(8) . . ?
C7 C8 S1 119.3(7) . . ?
C10 C8 S1 121.6(11) . . ?
C4 C3 C2 118.7(9) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?

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
C3 C4 C9 C5 177.8(16) . . . . ?
C3 C4 C9 C10 0(3) . . . . ?
C8 S1 C11 C12 -59.1(10) . . . . ?
S1 C11 C12 C12 109.3(18) . . . 5_666 ?
S1 C11 C12 I1 -68.8(10) . . . . ?
C4 C9 C5 C6 -179.2(19) . . . . ?
C10 C9 C5 C6 -1(3) . . . . ?
C2 N1 C10 C8 177.0(16) . . . . ?
C2 N1 C10 C9 -1(2) . . . . ?
C5 C9 C10 N1 -176.9(15) . . . . ?
C4 C9 C10 N1 1(2) . . . . ?
C5 C9 C10 C8 5(2) . . . . ?
C4 C9 C10 C8 -176.7(15) . . . . ?
C9 C5 C6 C7 -3(3) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C10 N1 C2 C3 0(2) . . . . ?
C6 C7 C8 C10 1(3) . . . . ?
C6 C7 C8 S1 178.1(16) . . . . ?
N1 C10 C8 C7 177.0(15) . . . . ?
C9 C10 C8 C7 -5(2) . . . . ?
N1 C10 C8 S1 0(2) . . . . ?
C9 C10 C8 S1 178.2(13) . . . . ?
C11 S1 C8 C7 103.0(15) . . . . ?
C11 S1 C8 C10 -80.3(17) . . . . ?
C9 C4 C3 C2 -1(3) . . . . ?
N1 C2 C3 C4 1(3) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_105GPa
_database_code_depnum_ccdc_archive 'CCDC 2466422'
loop_
_audit_author_name
_audit_author_address
'Nikita Bogdanov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I5 N2 S2'
_chemical_formula_weight         1007.99

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.1989(4)
_cell_length_b                   10.8516(2)
_cell_length_c                   18.127(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.788(9)
_cell_angle_gamma                90
_cell_volume                     2565.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3835
_cell_measurement_theta_min      2.4390
_cell_measurement_theta_max      27.4010

_exptl_crystal_description       block
_exptl_crystal_colour            ruby-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.609
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.238
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.04274
_exptl_absorpt_correction_T_max  0.06636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_oxdiff_exptl_absorpt_empirical_full_max 1.293
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            8099
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         27.941
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.321
_diffrn_measured_fraction_theta_full 0.356
_diffrn_reflns_Laue_measured_fraction_max 0.321
_diffrn_reflns_Laue_measured_fraction_full 0.356
_diffrn_reflns_point_group_measured_fraction_max 0.321
_diffrn_reflns_point_group_measured_fraction_full 0.356
_reflns_number_total             991
_reflns_number_gt                818
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0428P)²+9.1411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         991
_refine_ls_number_parameters     142
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      0.968
_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
I1 I 0.57623(5) 0.29134(5) 0.47938(9) 0.0632(12) Uani 1 1 d . U . . .
C4 C 0.1972(6) 0.6537(7) 0.6743(12) 0.045(7) Uani 1 1 d . U . . .
H4 H 0.128461 0.673177 0.659636 0.054 Uiso 1 1 calc R U . . .
I2 I 0.500000 -0.00222(6) 0.750000 0.0667(14) Uani 1 2 d S TU P . .
I3 I 0.36816(5) -0.00707(5) 0.60666(11) 0.0802(13) Uani 1 1 d . U . . .
C9 C 0.2374(5) 0.5453(6) 0.6478(11) 0.047(7) Uani 1 1 d . U . . .
S1 S 0.51957(16) 0.38076(17) 0.6635(3) 0.055(3) Uani 1 1 d . U . . .
C11 C 0.5730(7) 0.4841(9) 0.5981(18) 0.055(5) Uani 1 1 d . U . . .
H11A H 0.559244 0.568909 0.610326 0.066 Uiso 1 1 calc R U . . .
H11B H 0.646772 0.473418 0.604415 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5323(7) 0.4620(9) 0.5242(16) 0.051(5) Uani 1 1 d . U . . .
N1 N 0.4017(4) 0.5975(5) 0.7180(8) 0.045(6) Uani 1 1 d D U . . .
H1 H 0.500000 0.587(8) 0.750000 0.055 Uiso 1 2 d DS U P . .
C5 C 0.1770(6) 0.4600(8) 0.6001(13) 0.050(8) Uani 1 1 d . U . . .
H5 H 0.108068 0.476125 0.583572 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3434(5) 0.5206(6) 0.6675(12) 0.047(6) Uani 1 1 d . U . . .
C6 C 0.2193(7) 0.3583(9) 0.5795(14) 0.060(8) Uani 1 1 d . U . . .
H6 H 0.177051 0.299083 0.553519 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3246(7) 0.3348(8) 0.5947(13) 0.051(8) Uani 1 1 d . U . . .
H7 H 0.352371 0.265937 0.574633 0.062 Uiso 1 1 calc R U . . .
C2 C 0.3598(6) 0.6972(6) 0.7425(12) 0.054(7) Uani 1 1 d . U . . .
H2 H 0.400206 0.748645 0.775911 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3871(5) 0.4158(6) 0.6401(11) 0.048(6) Uani 1 1 d . U . . .
C3 C 0.2562(6) 0.7284(6) 0.7197(12) 0.048(8) Uani 1 1 d . U . . .
H3 H 0.229591 0.800712 0.736542 0.058 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 C12 2.137(12) . ?
C4 C3 1.32(2) . ?
C4 C9 1.404(14) . ?
C4 H4 0.9300 . ?
I2 I3 2.8984(18) 2_656 ?
I2 I3 2.8984(18) . ?
C9 C10 1.416(12) . ?
C9 C5 1.42(2) . ?
S1 C8 1.777(8) . ?
S1 C11 1.85(2) . ?
C11 C12 1.39(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.40(4) 5_666 ?
N1 C2 1.322(12) . ?
N1 C10 1.383(17) . ?
N1 H1 1.343(10) . ?
C5 C6 1.317(15) . ?
C5 H5 0.9300 . ?
C10 C8 1.399(13) . ?
C6 C7 1.399(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.39(2) . ?
C7 H7 0.9300 . ?
C2 C3 1.407(14) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C3 C4 C9 120.6(9) . . ?
C3 C4 H4 119.7 . . ?
C9 C4 H4 119.7 . . ?
I3 I2 I3 177.92(3) 2_656 . ?
C4 C9 C10 118.9(12) . . ?
C4 C9 C5 123.1(9) . . ?
C10 C9 C5 118.0(9) . . ?
C8 S1 C11 100.1(7) . . ?
C12 C11 S1 112.7(9) . . ?
C12 C11 H11A 109.1 . . ?
S1 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
S1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C12 127.9(17) . 5_666 ?
C11 C12 I1 115.5(12) . . ?
C12 C12 I1 117(2) 5_666 . ?
C2 N1 C10 119.8(8) . . ?
C2 N1 H1 111(4) . . ?
C10 N1 H1 130(3) . . ?
C6 C5 C9 119.7(10) . . ?
C6 C5 H5 120.2 . . ?
C9 C5 H5 120.2 . . ?
N1 C10 C8 120.5(8) . . ?
N1 C10 C9 118.7(9) . . ?
C8 C10 C9 120.6(12) . . ?
C5 C6 C7 123.3(14) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C8 C7 C6 118.9(11) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N1 C2 C3 122.4(13) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C7 C8 C10 119.1(8) . . ?
C7 C8 S1 118.6(6) . . ?
C10 C8 S1 122.3(10) . . ?
C4 C3 C2 119.3(9) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?

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
C3 C4 C9 C10 -3(2) . . . . ?
C3 C4 C9 C5 178.5(16) . . . . ?
C8 S1 C11 C12 -57.9(9) . . . . ?
S1 C11 C12 C12 111.7(19) . . . 5_666 ?
S1 C11 C12 I1 -69.2(10) . . . . ?
C4 C9 C5 C6 -177.8(18) . . . . ?
C10 C9 C5 C6 4(3) . . . . ?
C2 N1 C10 C8 178.9(15) . . . . ?
C2 N1 C10 C9 -5(2) . . . . ?
C4 C9 C10 N1 6(2) . . . . ?
C5 C9 C10 N1 -175.4(14) . . . . ?
C4 C9 C10 C8 -177.7(16) . . . . ?
C5 C9 C10 C8 0(2) . . . . ?
C9 C5 C6 C7 -8(3) . . . . ?
C5 C6 C7 C8 7(3) . . . . ?
C10 N1 C2 C3 1(2) . . . . ?
C6 C7 C8 C10 -2(3) . . . . ?
C6 C7 C8 S1 176.5(15) . . . . ?
N1 C10 C8 C7 174.4(14) . . . . ?
C9 C10 C8 C7 -1(3) . . . . ?
N1 C10 C8 S1 -4(2) . . . . ?
C9 C10 C8 S1 -179.8(13) . . . . ?
C11 S1 C8 C7 101.4(15) . . . . ?
C11 S1 C8 C10 -80.2(16) . . . . ?
C9 C4 C3 C2 -1(2) . . . . ?
N1 C2 C3 C4 2(3) . . . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.080

