# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2333378'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-04-29 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         'C12 H14 Cl N S2'
_chemical_formula_sum            'C12 H14 Cl N S2'
_chemical_formula_weight         271.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.1840(2)
_cell_length_b                   6.11460(10)
_cell_length_c                   15.3680(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.952(2)
_cell_angle_gamma                90
_cell_volume                     1271.85(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10642
_cell_measurement_theta_max      76.2760
_cell_measurement_theta_min      3.2290

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    5.485
_shelx_estimated_absorpt_T_min   0.550
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16087
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.265
_diffrn_reflns_theta_max         66.957
_diffrn_reflns_theta_full        66.957
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2276
_reflns_number_gt                2164
_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          
;
Two conformations were noted for the ethylene link (C3-C4) of the pyrrolidine
ring. From fractional refinement, the major component (anisotropic) had
a site occupancy of 0.878(6) cf. 0.122(6) for the minor component 
(isotropic).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+0.5791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2276
_refine_ls_number_parameters     154
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.035
_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
Cl1 Cl 0.03704(3) 0.78163(7) 0.07273(2) 0.03220(11) Uani 1 1 d . . . . .
S1 S 0.30363(2) -0.00903(5) 0.60442(2) 0.02079(10) Uani 1 1 d . . . . .
S2 S 0.34950(2) 0.40818(5) 0.52454(2) 0.01962(10) Uani 1 1 d . . . . .
N1 N 0.47825(8) 0.11240(17) 0.62152(7) 0.0147(2) Uani 1 1 d . . . . .
C1 C 0.38237(9) 0.1553(2) 0.58766(8) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.52648(10) -0.0787(2) 0.68325(10) 0.0201(3) Uani 1 1 d D . . . .
H2A H 0.510433 -0.214764 0.644125 0.024 Uiso 1 1 calc R U . A 1
H2B H 0.506548 -0.095453 0.735948 0.024 Uiso 1 1 calc R U . A 1
C3 C 0.63677(11) -0.0229(3) 0.72493(13) 0.0216(5) Uani 0.878(6) 1 d . . P B 1
H3A H 0.659525 0.061925 0.786196 0.026 Uiso 0.878(6) 1 calc R U P B 1
H3B H 0.677118 -0.157364 0.738003 0.026 Uiso 0.878(6) 1 calc R U P B 1
C4 C 0.64332(13) 0.1137(3) 0.6449(2) 0.0211(5) Uani 0.878(6) 1 d . . P B 1
H4A H 0.703155 0.206826 0.671743 0.025 Uiso 0.878(6) 1 calc R U P B 1
H4B H 0.644033 0.019480 0.592821 0.025 Uiso 0.878(6) 1 calc R U P B 1
C3' C 0.6228(7) -0.1114(18) 0.6823(10) 0.017(3) Uiso 0.122(6) 1 d D . P B 2
H3C H 0.616348 -0.197216 0.625036 0.020 Uiso 0.122(6) 1 calc R U P B 2
H3D H 0.672416 -0.180224 0.743078 0.020 Uiso 0.122(6) 1 calc R U P B 2
C4' C 0.6453(8) 0.1264(17) 0.6749(10) 0.013(4) Uiso 0.122(6) 1 d D . P B 2
H4C H 0.694190 0.137822 0.649066 0.016 Uiso 0.122(6) 1 calc R U P B 2
H4D H 0.674509 0.193436 0.740687 0.016 Uiso 0.122(6) 1 calc R U P B 2
C5 C 0.55027(9) 0.2509(2) 0.60698(10) 0.0186(3) Uani 1 1 d D . . . .
H5A H 0.562205 0.389140 0.644184 0.022 Uiso 1 1 calc R U . B 1
H5B H 0.526387 0.285901 0.537003 0.022 Uiso 1 1 calc R U . B 1
C6 C 0.21700(9) 0.4281(2) 0.48257(10) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.189718 0.282093 0.484437 0.026 Uiso 1 1 calc R U . . .
H6B H 0.203218 0.527189 0.525875 0.026 Uiso 1 1 calc R U . . .
C7 C 0.16904(9) 0.5152(2) 0.37974(9) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.17013(9) 0.3915(2) 0.30396(10) 0.0190(3) Uani 1 1 d . . . . .
H8 H 0.199568 0.250443 0.317581 0.023 Uiso 1 1 calc R U . . .
C9 C 0.12910(9) 0.4704(2) 0.20930(10) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.130077 0.385248 0.158044 0.025 Uiso 1 1 calc R U . . .
C10 C 0.08651(9) 0.6768(2) 0.19097(9) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.08249(9) 0.8019(2) 0.26405(10) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.051541 0.941342 0.249782 0.022 Uiso 1 1 calc R U . . .
C12 C 0.12442(9) 0.7203(2) 0.35866(9) 0.0171(3) Uani 1 1 d . . . . .
H12 H 0.122636 0.805414 0.409549 0.021 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
Cl1 C10 1.7434(13) . ?
S1 C1 1.6685(12) . ?
S2 C1 1.7728(13) . ?
S2 C6 1.8172(13) . ?
N1 C1 1.3313(17) . ?
N1 C2 1.4738(16) . ?
N1 C5 1.4781(16) . ?
C2 C3' 1.483(8) . ?
C2 C3 1.536(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3' C4' 1.509(9) . ?
C3' H3C 0.9900 . ?
C3' H3D 0.9900 . ?
C4' C5 1.545(9) . ?
C4' H4C 0.9900 . ?
C4' H4D 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5062(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3918(18) . ?
C7 C8 1.3952(19) . ?
C8 C9 1.3842(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3829(19) . ?
C11 C12 1.3889(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C1 S2 C6 104.15(6) . . ?
C1 N1 C2 122.96(10) . . ?
C1 N1 C5 125.52(10) . . ?
C2 N1 C5 111.46(10) . . ?
N1 C1 S1 123.66(10) . . ?
N1 C1 S2 111.86(9) . . ?
S1 C1 S2 124.47(7) . . ?
N1 C2 C3' 107.7(4) . . ?
N1 C2 C3 102.82(11) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 104.03(13) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C3 102.88(15) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C2 C3' C4' 97.4(8) . . ?
C2 C3' H3C 112.3 . . ?
C4' C3' H3C 112.3 . . ?
C2 C3' H3D 112.3 . . ?
C4' C3' H3D 112.3 . . ?
H3C C3' H3D 109.9 . . ?
C3' C4' C5 110.6(8) . . ?
C3' C4' H4C 109.5 . . ?
C5 C4' H4C 109.5 . . ?
C3' C4' H4D 109.5 . . ?
C5 C4' H4D 109.5 . . ?
H4C C4' H4D 108.1 . . ?
N1 C5 C4 104.44(11) . . ?
N1 C5 C4' 98.3(5) . . ?
N1 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
N1 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 S2 109.09(9) . . ?
C7 C6 H6A 109.9 . . ?
S2 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
S2 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C12 C7 C8 118.89(12) . . ?
C12 C7 C6 121.05(12) . . ?
C8 C7 C6 120.06(12) . . ?
C9 C8 C7 121.21(12) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.48(12) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 121.75(12) . . ?
C11 C10 Cl1 119.11(11) . . ?
C9 C10 Cl1 119.14(11) . . ?
C10 C11 C12 118.91(12) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 120.74(12) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

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
C2 N1 C1 S1 -4.16(17) . . . . ?
C5 N1 C1 S1 178.85(10) . . . . ?
C2 N1 C1 S2 175.06(9) . . . . ?
C5 N1 C1 S2 -1.93(16) . . . . ?
C6 S2 C1 N1 178.41(9) . . . . ?
C6 S2 C1 S1 -2.37(10) . . . . ?
C1 N1 C2 C3' 163.3(6) . . . . ?
C5 N1 C2 C3' -19.3(6) . . . . ?
C1 N1 C2 C3 -165.21(12) . . . . ?
C5 N1 C2 C3 12.16(15) . . . . ?
N1 C2 C3 C4 -30.95(19) . . . . ?
C2 C3 C4 C5 38.3(2) . . . . ?
N1 C2 C3' C4' 33.5(11) . . . . ?
C2 C3' C4' C5 -38.3(14) . . . . ?
C1 N1 C5 C4 -171.16(16) . . . . ?
C2 N1 C5 C4 11.56(18) . . . . ?
C1 N1 C5 C4' 172.6(6) . . . . ?
C2 N1 C5 C4' -4.7(6) . . . . ?
C3 C4 C5 N1 -30.5(2) . . . . ?
C3' C4' C5 N1 27.5(12) . . . . ?
C1 S2 C6 C7 -138.39(10) . . . . ?
S2 C6 C7 C12 -113.14(12) . . . . ?
S2 C6 C7 C8 65.90(14) . . . . ?
C12 C7 C8 C9 0.94(18) . . . . ?
C6 C7 C8 C9 -178.12(12) . . . . ?
C7 C8 C9 C10 0.02(19) . . . . ?
C8 C9 C10 C11 -1.32(19) . . . . ?
C8 C9 C10 Cl1 178.51(10) . . . . ?
C9 C10 C11 C12 1.60(19) . . . . ?
Cl1 C10 C11 C12 -178.23(9) . . . . ?
C10 C11 C12 C7 -0.59(18) . . . . ?
C8 C7 C12 C11 -0.65(18) . . . . ?
C6 C7 C12 C11 178.40(11) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2333382'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-02-17 deposited with the CCDC.	2024-04-29 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         'C12 H14 N2 O2 S2'
_chemical_formula_sum            'C12 H14 N2 O2 S2'
_chemical_formula_weight         282.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   13.9471(5)
_cell_length_b                   11.0713(3)
_cell_length_c                   8.2857(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1279.42(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5643
_cell_measurement_theta_min      5.0620
_cell_measurement_theta_max      76.4990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    3.746
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8946
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.101
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_full        67.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2255
_reflns_number_gt                2169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.974

_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          
;
Owing to poor agreement, five reflections, i.e. (7 0 8), (1 0 8), (4 0 7), 
(1 1 7) and (2 0 8), were omitted from the final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.2125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_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
S1 S 0.36599(7) 0.67729(8) 0.45589(12) 0.0176(3) Uani 1 1 d . . . . .
S2 S 0.38231(6) 0.40387(7) 0.49568(12) 0.0166(3) Uani 1 1 d . . . . .
O1 O -0.1114(2) 0.5436(3) 0.2327(4) 0.0262(7) Uani 1 1 d . . . . .
O2 O -0.1046(2) 0.3489(3) 0.2082(4) 0.0260(7) Uani 1 1 d . . . . .
N1 N 0.5092(2) 0.5394(3) 0.3559(4) 0.0152(7) Uani 1 1 d . . . . .
N2 N -0.0729(3) 0.4450(3) 0.2593(4) 0.0189(8) Uani 1 1 d . . . . .
C1 C 0.4252(3) 0.5471(3) 0.4285(5) 0.0159(8) Uani 1 1 d . . . . .
C2 C 0.5598(3) 0.6462(4) 0.2915(6) 0.0205(9) Uani 1 1 d . . . . .
H2A H 0.572933 0.705492 0.378237 0.025 Uiso 1 1 calc R U . . .
H2B H 0.521609 0.685931 0.205978 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6529(3) 0.5953(4) 0.2233(7) 0.0274(10) Uani 1 1 d . . . . .
H3A H 0.706660 0.652218 0.240818 0.033 Uiso 1 1 calc R U . . .
H3B H 0.646701 0.579283 0.106222 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6688(3) 0.4784(4) 0.3164(7) 0.0269(10) Uani 1 1 d . . . . .
H4A H 0.709372 0.421579 0.254277 0.032 Uiso 1 1 calc R U . . .
H4B H 0.699343 0.494211 0.422134 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5682(3) 0.4291(3) 0.3374(5) 0.0186(9) Uani 1 1 d . . . . .
H5A H 0.548077 0.381956 0.241693 0.022 Uiso 1 1 calc R U . . .
H5B H 0.563783 0.377169 0.434410 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2783(3) 0.4406(4) 0.6175(5) 0.0170(8) Uani 1 1 d . . . . .
H6A H 0.273271 0.381167 0.706386 0.020 Uiso 1 1 calc R U . . .
H6B H 0.288036 0.521196 0.666697 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1854(3) 0.4416(3) 0.5256(5) 0.0155(8) Uani 1 1 d . . . . .
C8 C 0.1514(3) 0.3364(3) 0.4521(5) 0.0164(8) Uani 1 1 d . . . . .
H8 H 0.187050 0.263645 0.461899 0.020 Uiso 1 1 calc R U . . .
C9 C 0.0664(3) 0.3361(3) 0.3653(5) 0.0173(8) Uani 1 1 d . . . . .
H9 H 0.043880 0.264622 0.314599 0.021 Uiso 1 1 calc R U . . .
C10 C 0.0152(3) 0.4436(4) 0.3545(5) 0.0159(8) Uani 1 1 d . . . . .
C11 C 0.0458(3) 0.5494(3) 0.4275(5) 0.0176(8) Uani 1 1 d . . . . .
H11 H 0.009344 0.621628 0.418749 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1309(3) 0.5473(3) 0.5135(5) 0.0179(8) Uani 1 1 d . . . . .
H12 H 0.152577 0.618805 0.565210 0.021 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
S1 C1 1.677(4) . ?
S2 C1 1.784(4) . ?
S2 C6 1.814(4) . ?
O1 N2 1.237(5) . ?
O2 N2 1.228(5) . ?
N1 C1 1.320(5) . ?
N1 C2 1.477(5) . ?
N1 C5 1.481(5) . ?
N2 C10 1.459(5) . ?
C2 C3 1.524(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.398(5) . ?
C7 C12 1.400(5) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C1 S2 C6 104.04(18) . . ?
C1 N1 C2 122.5(3) . . ?
C1 N1 C5 126.4(3) . . ?
C2 N1 C5 110.9(3) . . ?
O2 N2 O1 123.2(3) . . ?
O2 N2 C10 118.7(3) . . ?
O1 N2 C10 118.1(3) . . ?
N1 C1 S1 123.7(3) . . ?
N1 C1 S2 112.5(3) . . ?
S1 C1 S2 123.8(2) . . ?
N1 C2 C3 104.2(3) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 104.5(4) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 103.3(4) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 103.3(3) . . ?
N1 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 S2 114.1(3) . . ?
C7 C6 H6A 108.7 . . ?
S2 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
S2 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C12 118.7(4) . . ?
C8 C7 C6 120.6(3) . . ?
C12 C7 C6 120.7(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.1(3) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 N2 119.1(3) . . ?
C9 C10 N2 118.5(4) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?

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
C2 N1 C1 S1 0.2(6) . . . . ?
C5 N1 C1 S1 175.6(3) . . . . ?
C2 N1 C1 S2 -179.3(3) . . . . ?
C5 N1 C1 S2 -3.8(5) . . . . ?
C6 S2 C1 N1 171.1(3) . . . . ?
C6 S2 C1 S1 -8.4(3) . . . . ?
C1 N1 C2 C3 178.8(4) . . . . ?
C5 N1 C2 C3 2.7(5) . . . . ?
N1 C2 C3 C4 -24.3(5) . . . . ?
C2 C3 C4 C5 36.7(5) . . . . ?
C1 N1 C5 C4 -155.9(4) . . . . ?
C2 N1 C5 C4 20.0(5) . . . . ?
C3 C4 C5 N1 -34.3(5) . . . . ?
C1 S2 C6 C7 91.6(3) . . . . ?
S2 C6 C7 C8 62.3(5) . . . . ?
S2 C6 C7 C12 -118.5(4) . . . . ?
C12 C7 C8 C9 1.6(6) . . . . ?
C6 C7 C8 C9 -179.2(4) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C8 C9 C10 N2 178.2(4) . . . . ?
O2 N2 C10 C11 -173.0(4) . . . . ?
O1 N2 C10 C11 7.8(6) . . . . ?
O2 N2 C10 C9 8.5(6) . . . . ?
O1 N2 C10 C9 -170.7(4) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
N2 C10 C11 C12 -178.2(4) . . . . ?
C10 C11 C12 C7 0.6(6) . . . . ?
C8 C7 C12 C11 -1.5(6) . . . . ?
C6 C7 C12 C11 179.2(4) . . . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2333380'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-02-17 deposited with the CCDC.	2024-04-29 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         'C12 H14 I N S2'
_chemical_formula_sum            'C12 H14 I N S2'
_chemical_formula_weight         363.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.0797(2)
_cell_length_b                   9.72500(10)
_cell_length_c                   12.7025(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.262(2)
_cell_angle_gamma                90
_cell_volume                     1326.47(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10860
_cell_measurement_theta_min      4.1520
_cell_measurement_theta_max      75.9290

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    21.682
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.342
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.144
_exptl_absorpt_correction_T_max  0.498
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17007
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.185
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2744
_reflns_number_gt                2621
_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0318P)²+0.5461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2744
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0548
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.98170(2) 0.49973(2) 0.83375(2) 0.01840(7) Uani 1 1 d . . . . .
S1 S 0.28957(4) 0.52810(6) 0.07097(4) 0.02003(11) Uani 1 1 d . . . . .
S2 S 0.53421(4) 0.38880(5) 0.22966(4) 0.01732(10) Uani 1 1 d . . . . .
N1 N 0.40366(13) 0.33939(17) 0.00519(12) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.40230(16) 0.4163(2) 0.09072(15) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.30690(17) 0.3505(2) -0.11937(15) 0.0182(4) Uani 1 1 d . . . . .
H2A H 0.301333 0.445594 -0.149293 0.022 Uiso 1 1 calc R U . . .
H2B H 0.224373 0.322474 -0.128008 0.022 Uiso 1 1 calc R U . . .
C3 C 0.35263(17) 0.2513(2) -0.18420(16) 0.0198(4) Uani 1 1 d . . . . .
H3A H 0.409874 0.297732 -0.208969 0.024 Uiso 1 1 calc R U . . .
H3B H 0.282055 0.211550 -0.254795 0.024 Uiso 1 1 calc R U . . .
C4 C 0.42064(18) 0.1408(2) -0.09086(16) 0.0202(4) Uani 1 1 d . . . . .
H4A H 0.478560 0.087491 -0.110482 0.024 Uiso 1 1 calc R U . . .
H4B H 0.361125 0.076976 -0.082770 0.024 Uiso 1 1 calc R U . . .
C5 C 0.49100(17) 0.2257(2) 0.02129(17) 0.0195(4) Uani 1 1 d . . . . .
H5A H 0.508064 0.171283 0.092999 0.023 Uiso 1 1 calc R U . . .
H5B H 0.570636 0.260531 0.027157 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4944(2) 0.4798(2) 0.33255(18) 0.0208(5) Uani 1 1 d . . . . .
H6A H 0.467507 0.574732 0.304272 0.025 Uiso 1 1 calc R U . . .
H6B H 0.425364 0.432287 0.339138 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6086(2) 0.4825(2) 0.45116(19) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.64824(17) 0.3649(2) 0.52179(16) 0.0184(4) Uani 1 1 d . . . . .
H8 H 0.602755 0.281725 0.494554 0.022 Uiso 1 1 calc R U . . .
C9 C 0.75354(17) 0.3679(2) 0.63164(16) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.779754 0.287587 0.679410 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8200(2) 0.49060(18) 0.67055(18) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.78153(17) 0.6087(2) 0.60161(16) 0.0188(4) Uani 1 1 d . . . . .
H11 H 0.826635 0.692107 0.629077 0.023 Uiso 1 1 calc R U . . .
C12 C 0.67608(17) 0.6037(2) 0.49168(16) 0.0188(4) Uani 1 1 d . . . . .
H12 H 0.650045 0.684042 0.443924 0.023 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 C10 2.100(2) . ?
S1 C1 1.6694(19) . ?
S2 C1 1.7745(18) . ?
S2 C6 1.816(2) . ?
N1 C1 1.325(2) . ?
N1 C5 1.476(2) . ?
N1 C2 1.479(2) . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.507(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.391(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C11 C12 1.395(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C1 S2 C6 103.25(9) . . ?
C1 N1 C5 125.83(15) . . ?
C1 N1 C2 122.35(15) . . ?
C5 N1 C2 111.57(14) . . ?
N1 C1 S1 124.05(13) . . ?
N1 C1 S2 112.81(13) . . ?
S1 C1 S2 123.13(11) . . ?
N1 C2 C3 103.11(14) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 102.96(14) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 102.42(16) . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
C5 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C4 102.65(14) . . ?
N1 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
N1 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 S2 107.78(15) . . ?
C7 C6 H6A 110.2 . . ?
S2 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
S2 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C12 C7 C8 119.08(19) . . ?
C12 C7 C6 119.86(18) . . ?
C8 C7 C6 121.06(19) . . ?
C9 C8 C7 120.94(19) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 119.04(18) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.76(19) . . ?
C9 C10 I1 120.63(14) . . ?
C11 C10 I1 118.60(14) . . ?
C10 C11 C12 119.40(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.77(19) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?

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
C5 N1 C1 S1 -170.66(14) . . . . ?
C2 N1 C1 S1 3.2(3) . . . . ?
C5 N1 C1 S2 9.7(2) . . . . ?
C2 N1 C1 S2 -176.48(13) . . . . ?
C6 S2 C1 N1 -169.74(14) . . . . ?
C6 S2 C1 S1 10.59(15) . . . . ?
C1 N1 C2 C3 176.14(16) . . . . ?
C5 N1 C2 C3 -9.22(19) . . . . ?
N1 C2 C3 C4 31.22(18) . . . . ?
C2 C3 C4 C5 -41.76(18) . . . . ?
C1 N1 C5 C4 157.82(17) . . . . ?
C2 N1 C5 C4 -16.6(2) . . . . ?
C3 C4 C5 N1 35.46(18) . . . . ?
C1 S2 C6 C7 -171.11(14) . . . . ?
S2 C6 C7 C12 105.72(19) . . . . ?
S2 C6 C7 C8 -74.3(2) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C6 C7 C8 C9 -179.72(18) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 I1 -178.64(13) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
I1 C10 C11 C12 178.46(14) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C6 C7 C12 C11 179.52(18) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.860
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2333381'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-04-29 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         'C13 H17 N S2'
_chemical_formula_sum            'C13 H17 N S2'
_chemical_formula_weight         251.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.4564(5)
_cell_length_b                   5.9662(2)
_cell_length_c                   17.6358(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.170(3)
_cell_angle_gamma                90
_cell_volume                     1285.82(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5024
_cell_measurement_theta_min      3.9910
_cell_measurement_theta_max      76.3130

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    3.513
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15655
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.004
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_full        67.045
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2291
_reflns_number_gt                1941
_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0458P)²+0.9239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
S1 S 0.84807(4) 0.35235(9) 0.52717(3) 0.02414(16) Uani 1 1 d . . . . .
S2 S 0.75246(4) 0.64548(9) 0.38936(3) 0.02294(16) Uani 1 1 d . . . . .
N1 N 0.89758(14) 0.3363(3) 0.38780(9) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.84096(16) 0.4310(4) 0.43533(11) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.97211(18) 0.1460(4) 0.41045(12) 0.0243(5) Uani 1 1 d . . . . .
H2A H 0.934559 0.022113 0.432108 0.029 Uiso 1 1 calc R U . . .
H2B H 1.037049 0.192159 0.449042 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0043(2) 0.0766(4) 0.33437(13) 0.0333(5) Uani 1 1 d . . . . .
H3A H 1.078789 0.011468 0.343524 0.040 Uiso 1 1 calc R U . . .
H3B H 0.951916 -0.033789 0.306266 0.040 Uiso 1 1 calc R U . . .
C4 C 1.00004(19) 0.2956(4) 0.28985(13) 0.0286(5) Uani 1 1 d . . . . .
H4A H 0.992085 0.267857 0.233686 0.034 Uiso 1 1 calc R U . . .
H4B H 1.066726 0.386057 0.307828 0.034 Uiso 1 1 calc R U . . .
C5 C 0.89931(17) 0.4114(4) 0.30801(11) 0.0241(5) Uani 1 1 d . . . . .
H5A H 0.906207 0.576449 0.305515 0.029 Uiso 1 1 calc R U . . .
H5B H 0.832269 0.363698 0.271777 0.029 Uiso 1 1 calc R U . . .
C6 C 0.67997(18) 0.7361(4) 0.46398(12) 0.0267(5) Uani 1 1 d . . . . .
H6A H 0.653100 0.604620 0.489048 0.032 Uiso 1 1 calc R U . . .
H6B H 0.729288 0.823782 0.503952 0.032 Uiso 1 1 calc R U . . .
C7 C 0.58492(17) 0.8793(4) 0.42537(11) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.60298(17) 1.0850(4) 0.39324(11) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.675818 1.135248 0.395160 0.028 Uiso 1 1 calc R U . . .
C9 C 0.51626(17) 1.2176(4) 0.35849(11) 0.0237(5) Uani 1 1 d . . . . .
H9 H 0.530533 1.357618 0.336762 0.028 Uiso 1 1 calc R U . . .
C10 C 0.40830(17) 1.1497(4) 0.35475(12) 0.0241(5) Uani 1 1 d . . . . .
C11 C 0.39063(17) 0.9433(4) 0.38687(12) 0.0239(5) Uani 1 1 d . . . . .
H11 H 0.317803 0.892934 0.384987 0.029 Uiso 1 1 calc R U . . .
C12 C 0.47736(17) 0.8097(4) 0.42156(12) 0.0233(5) Uani 1 1 d . . . . .
H12 H 0.463251 0.669132 0.442963 0.028 Uiso 1 1 calc R U . . .
C13 C 0.31426(19) 1.2967(4) 0.31741(14) 0.0334(6) Uani 1 1 d . . . . .
H13A H 0.342890 1.434245 0.298301 0.050 Uiso 0.5 1 calc R U P . .
H13B H 0.269309 1.216300 0.274143 0.050 Uiso 0.5 1 calc R U P . .
H13C H 0.269498 1.335141 0.355519 0.050 Uiso 0.5 1 calc R U P . .
H13D H 0.244908 1.222879 0.320341 0.050 Uiso 0.5 1 calc R U P . .
H13E H 0.318489 1.440824 0.344499 0.050 Uiso 0.5 1 calc R U P . .
H13F H 0.318300 1.321983 0.263122 0.050 Uiso 0.5 1 calc R U P . .


_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
S1 C1 1.672(2) . ?
S2 C1 1.779(2) . ?
S2 C6 1.817(2) . ?
N1 C1 1.322(3) . ?
N1 C2 1.472(3) . ?
N1 C5 1.481(2) . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.511(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.392(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 C13 1.509(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S2 C6 103.60(10) . . ?
C1 N1 C2 122.92(17) . . ?
C1 N1 C5 125.51(17) . . ?
C2 N1 C5 111.51(16) . . ?
N1 C1 S1 124.02(16) . . ?
N1 C1 S2 112.22(14) . . ?
S1 C1 S2 123.73(12) . . ?
N1 C2 C3 103.26(17) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 103.40(19) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 103.28(18) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 103.13(16) . . ?
N1 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 S2 107.32(14) . . ?
C7 C6 H6A 110.2 . . ?
S2 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
S2 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C12 C7 C8 118.3(2) . . ?
C12 C7 C6 121.1(2) . . ?
C8 C7 C6 120.60(19) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 117.7(2) . . ?
C11 C10 C13 121.5(2) . . ?
C9 C10 C13 120.8(2) . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 S1 1.3(3) . . . . ?
C5 N1 C1 S1 -175.47(16) . . . . ?
C2 N1 C1 S2 -176.53(15) . . . . ?
C5 N1 C1 S2 6.7(3) . . . . ?
C6 S2 C1 N1 176.99(16) . . . . ?
C6 S2 C1 S1 -0.89(17) . . . . ?
C1 N1 C2 C3 172.2(2) . . . . ?
C5 N1 C2 C3 -10.6(2) . . . . ?
N1 C2 C3 C4 30.8(2) . . . . ?
C2 C3 C4 C5 -39.7(2) . . . . ?
C1 N1 C5 C4 163.3(2) . . . . ?
C2 N1 C5 C4 -13.8(2) . . . . ?
C3 C4 C5 N1 32.7(2) . . . . ?
C1 S2 C6 C7 -167.13(15) . . . . ?
S2 C6 C7 C12 113.91(19) . . . . ?
S2 C6 C7 C8 -66.6(2) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C6 C7 C8 C9 -179.38(19) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C13 179.38(19) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C13 C10 C11 C12 -179.55(19) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C6 C7 C12 C11 179.21(18) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2333379'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-02-17 deposited with the CCDC.	2024-04-29 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         'C12 H14 Br N S2'
_chemical_formula_sum            'C12 H14 Br N S2'
_chemical_formula_weight         316.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.1754(2)
_cell_length_b                   9.64310(10)
_cell_length_c                   12.3470(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.889(2)
_cell_angle_gamma                90
_cell_volume                     1281.28(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11810
_cell_measurement_theta_min      4.1860
_cell_measurement_theta_max      76.3650

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    7.181
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15897
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.209
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_full        67.055
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2294
_reflns_number_gt                2229
_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0221P)²+0.6034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2294
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0442
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.97154(2) 0.48758(2) 0.83302(2) 0.02117(7) Uani 1 1 d . . . . .
S1 S 0.28658(3) 0.53144(4) 0.06235(3) 0.01996(9) Uani 1 1 d . . . . .
S2 S 0.53163(3) 0.39029(4) 0.22468(3) 0.01608(9) Uani 1 1 d . . . . .
N1 N 0.39590(11) 0.33874(12) -0.00672(10) 0.0148(2) Uani 1 1 d . . . . .
C1 C 0.39783(13) 0.41783(14) 0.08221(13) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.29674(13) 0.34884(16) -0.13486(13) 0.0175(3) Uani 1 1 d . . . . .
H2A H 0.289927 0.444419 -0.166659 0.021 Uiso 1 1 calc R U . . .
H2B H 0.215414 0.320379 -0.142189 0.021 Uiso 1 1 calc R U . . .
C3 C 0.34008(14) 0.24826(16) -0.20252(13) 0.0200(3) Uani 1 1 d . . . . .
H3A H 0.268551 0.207560 -0.274656 0.024 Uiso 1 1 calc R U . . .
H3B H 0.395383 0.294953 -0.229687 0.024 Uiso 1 1 calc R U . . .
C4 C 0.41014(14) 0.13787(16) -0.10624(14) 0.0200(3) Uani 1 1 d . . . . .
H4A H 0.352094 0.073151 -0.096751 0.024 Uiso 1 1 calc R U . . .
H4B H 0.466862 0.084432 -0.127441 0.024 Uiso 1 1 calc R U . . .
C5 C 0.48231(13) 0.22364(16) 0.00934(13) 0.0188(3) Uani 1 1 d . . . . .
H5A H 0.500732 0.169026 0.083807 0.023 Uiso 1 1 calc R U . . .
H5B H 0.561154 0.258427 0.014587 0.023 Uiso 1 1 calc R U . . .
C6 C 0.49570(14) 0.48297(16) 0.33223(13) 0.0186(3) Uani 1 1 d . . . . .
H6A H 0.470743 0.579474 0.304108 0.022 Uiso 1 1 calc R U . . .
H6B H 0.426438 0.436895 0.338874 0.022 Uiso 1 1 calc R U . . .
C7 C 0.61112(14) 0.48218(15) 0.45459(13) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.65140(14) 0.36136(15) 0.52501(14) 0.0176(3) Uani 1 1 d . . . . .
H8 H 0.605473 0.277974 0.495077 0.021 Uiso 1 1 calc R U . . .
C9 C 0.75732(13) 0.36130(15) 0.63786(13) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.784039 0.278754 0.685127 0.021 Uiso 1 1 calc R U . . .
C10 C 0.82374(14) 0.48385(15) 0.68069(13) 0.0160(3) Uani 1 1 d . . . . .
C11 C 0.78557(14) 0.60527(16) 0.61316(13) 0.0179(3) Uani 1 1 d . . . . .
H11 H 0.831518 0.688520 0.643761 0.022 Uiso 1 1 calc R U . . .
C12 C 0.67953(13) 0.60394(16) 0.50039(13) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.653076 0.686905 0.453703 0.021 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
Br1 C10 1.9002(15) . ?
S1 C1 1.6687(14) . ?
S2 C1 1.7714(14) . ?
S2 C6 1.8157(15) . ?
N1 C1 1.3280(19) . ?
N1 C5 1.4774(18) . ?
N1 C2 1.4776(17) . ?
C2 C3 1.526(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.507(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.397(2) . ?
C7 C8 1.398(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C1 S2 C6 103.19(7) . . ?
C1 N1 C5 125.75(12) . . ?
C1 N1 C2 122.48(12) . . ?
C5 N1 C2 111.54(11) . . ?
N1 C1 S1 123.80(11) . . ?
N1 C1 S2 112.79(10) . . ?
S1 C1 S2 123.41(8) . . ?
N1 C2 C3 103.04(11) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 103.15(11) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C3 102.62(12) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C4 102.69(11) . . ?
N1 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
N1 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 S2 107.46(10) . . ?
C7 C6 H6A 110.2 . . ?
S2 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
S2 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C12 C7 C8 118.64(13) . . ?
C12 C7 C6 120.09(13) . . ?
C8 C7 C6 121.26(13) . . ?
C9 C8 C7 121.06(14) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 118.96(14) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 121.20(14) . . ?
C11 C10 Br1 118.39(11) . . ?
C9 C10 Br1 120.40(11) . . ?
C10 C11 C12 119.27(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 120.86(14) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

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
C5 N1 C1 S1 -170.97(11) . . . . ?
C2 N1 C1 S1 3.12(19) . . . . ?
C5 N1 C1 S2 9.16(17) . . . . ?
C2 N1 C1 S2 -176.74(10) . . . . ?
C6 S2 C1 N1 -169.23(10) . . . . ?
C6 S2 C1 S1 10.91(11) . . . . ?
C1 N1 C2 C3 175.58(12) . . . . ?
C5 N1 C2 C3 -9.57(15) . . . . ?
N1 C2 C3 C4 31.25(14) . . . . ?
C2 C3 C4 C5 -41.47(14) . . . . ?
C1 N1 C5 C4 158.69(13) . . . . ?
C2 N1 C5 C4 -15.96(15) . . . . ?
C3 C4 C5 N1 34.92(14) . . . . ?
C1 S2 C6 C7 -172.57(10) . . . . ?
S2 C6 C7 C12 108.17(13) . . . . ?
S2 C6 C7 C8 -72.48(15) . . . . ?
C12 C7 C8 C9 -0.3(2) . . . . ?
C6 C7 C8 C9 -179.66(13) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C10 Br1 -178.53(10) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
Br1 C10 C11 C12 178.50(10) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
C8 C7 C12 C11 0.3(2) . . . . ?
C6 C7 C12 C11 179.62(13) . . . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049

