# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1951221'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institut des Sciences et Ingenierie Chimiques, Ecole Polytechnique Federale de Lausanne (EPFL)
Switzerland
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H32 N2 O2 S2'
_chemical_formula_sum            'C22 H32 N2 O2 S2'
_chemical_formula_weight         420.61

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

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

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

_cell_length_a                   4.9848(4)
_cell_length_b                   5.6250(5)
_cell_length_c                   21.347(3)
_cell_angle_alpha                90.584(9)
_cell_angle_beta                 90.140(8)
_cell_angle_gamma                107.702(8)
_cell_volume                     570.18(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    199.99(10)
_cell_measurement_reflns_used    1267
_cell_measurement_theta_min      6.1650
_cell_measurement_theta_max      75.5480

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             226
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    2.261
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -14 0.0255
0 0 14 0.0081
-3 2 -3 0.2560
3 -2 -1 0.4177
-3 1 -6 0.2404
-1 4 1 0.1660
-3 3 2 0.2479
0 -3 9 0.1053
0 2 12 0.0452
-2 -1 -10 0.1637

_diffrn_ambient_temperature      199.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  33.00   1.00    2.56    --  -40.66  38.00 -60.00   98
  2  ω     41.00  79.00   1.00    2.56    --   40.66 -99.00 -90.00   38
  3  ω     23.00  49.00   1.00    2.56    --   40.66-125.00-120.00   26
  4  ω     40.00  93.00   1.00   10.25    --  112.00 -45.00   0.00   53
  5  ω     98.00 138.00   1.00   10.25    --  112.00 -45.00   0.00   40
  6  ω    112.00 159.00   1.00   10.25    --  112.00 -15.00 -60.00   47
  7  ω    105.00 139.00   1.00   10.25    --  112.00 -61.00-150.00   34
  8  ω     66.00  93.00   1.00   10.25    --  112.00 -61.00-150.00   27
  9  ω     34.00  81.00   1.00   10.25    --  112.00 -15.00 -60.00   47
 10  ω     83.00 128.00   1.00   10.25    --  112.00  61.00 -60.00   45
 11  ω    146.00 172.00   1.00   10.25    --  112.00  61.00 -60.00   26
 12  ω    107.00 172.00   1.00   10.25    --  112.00  77.00  30.00   65
 13  ω    119.00 164.00   1.00   10.25    --  112.00  30.00 150.00   45
 14  ω    102.00 136.00   1.00   10.25    --  112.00 125.00 -30.00   34
 15  ω     65.00 145.00   1.00   10.25    --  112.00 -77.00  60.00   80
 16  ω     54.00 112.00   1.00   10.25    --  112.00-125.00  60.00   58
 17  ω     36.00 108.00   1.00   10.25    --  112.00 -94.00-120.00   72
 18  ω    -72.00   8.00   1.00    2.56    --  -40.66  77.00  60.00   80
 19  ω   -111.00 -16.00   1.00    2.56    --  -40.66 -38.00 120.00   95
 20  ω    -85.00 -55.00   1.00    2.56    --  -40.66-160.00-109.00   30
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3263
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.142
_diffrn_reflns_theta_max         75.947
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2231
_reflns_number_gt                1901
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²+0.3190P] 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         2231
_refine_ls_number_parameters     166
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.067
_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 0.63656(13) 0.79589(12) 0.44288(4) 0.0434(2) Uani 1 1 d . . . . .
O1 O 0.3725(5) 0.3493(7) 0.19753(15) 0.0832(10) Uani 1 1 d . . . . .
N1A N -0.0981(14) 0.2484(14) 0.1862(4) 0.0569(19) Uani 0.544(8) 1 d D U P A 1
H1A H -0.249548 0.285040 0.198397 0.068 Uiso 0.544(8) 1 calc R U P A 1
N1B N -0.0720(18) 0.318(2) 0.1672(4) 0.059(2) Uani 0.456(8) 1 d D U P A 2
H1B H -0.221423 0.367250 0.173521 0.071 Uiso 0.456(8) 1 calc R U P A 2
C1 C 0.9224(5) 1.0259(5) 0.47361(13) 0.0380(6) Uani 1 1 d . . . . .
C2 C 0.9661(6) 1.2408(5) 0.44059(16) 0.0459(7) Uani 1 1 d . . . . .
H2 H 1.112693 1.390250 0.449932 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7709(6) 1.2183(5) 0.39114(16) 0.0483(7) Uani 1 1 d . . . . .
H3 H 0.774883 1.351935 0.363938 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5775(6) 0.9898(5) 0.38576(15) 0.0417(6) Uani 1 1 d . . . . .
C5 C 0.3426(6) 0.9000(6) 0.33867(16) 0.0468(7) Uani 1 1 d . . . . .
H5A H 0.342115 1.040112 0.311038 0.056 Uiso 1 1 calc R U . . .
H5B H 0.160870 0.848630 0.361136 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3652(6) 0.6828(6) 0.29850(15) 0.0457(7) Uani 1 1 d . . . . .
H6A H 0.345170 0.535934 0.325341 0.055 Uiso 1 1 calc R U . . .
H6B H 0.553721 0.727249 0.278975 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1408(6) 0.6156(7) 0.24758(15) 0.0505(7) Uani 1 1 d . . . . .
H7A H -0.046748 0.571340 0.267545 0.061 Uiso 1 1 calc R U . . .
H7B H 0.160116 0.764482 0.221533 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1536(7) 0.4034(8) 0.20571(17) 0.0580(9) Uani 1 1 d D . . . .
C9A C -0.1414(16) 0.0247(15) 0.1467(3) 0.0628(16) Uani 0.544(8) 1 d D U P A 1
H9AA H -0.249608 -0.122790 0.170717 0.075 Uiso 0.544(8) 1 calc R U P A 1
H9AB H 0.044387 0.004004 0.137042 0.075 Uiso 0.544(8) 1 calc R U P A 1
C9B C -0.0728(18) 0.1452(18) 0.1152(5) 0.0683(19) Uani 0.456(8) 1 d D U P A 2
H9BA H 0.103198 0.098352 0.116211 0.082 Uiso 0.456(8) 1 calc R U P A 2
H9BB H -0.080802 0.228247 0.074877 0.082 Uiso 0.456(8) 1 calc R U P A 2
C10A C -0.292(2) 0.0301(19) 0.0872(4) 0.081(2) Uani 0.544(8) 1 d D U P A 1
H10A H -0.190647 0.181508 0.063648 0.097 Uiso 0.544(8) 1 calc R U P A 1
H10B H -0.483559 0.037415 0.096201 0.097 Uiso 0.544(8) 1 calc R U P A 1
C10B C -0.318(2) -0.0811(18) 0.1200(5) 0.080(2) Uani 0.456(8) 1 d D U P A 2
H10C H -0.489117 -0.028813 0.124808 0.096 Uiso 0.456(8) 1 calc R U P A 2
H10D H -0.296221 -0.169733 0.158656 0.096 Uiso 0.456(8) 1 calc R U P A 2
C11A C -0.310(5) -0.202(3) 0.0473(7) 0.105(4) Uani 0.544(8) 1 d D U P A 1
H11A H -0.318372 -0.162054 0.002912 0.157 Uiso 0.544(8) 1 calc R U P A 1
H11B H -0.480480 -0.335845 0.058430 0.157 Uiso 0.544(8) 1 calc R U P A 1
H11C H -0.144124 -0.255838 0.055127 0.157 Uiso 0.544(8) 1 calc R U P A 1
C11B C -0.363(6) -0.265(3) 0.0650(8) 0.096(5) Uani 0.456(8) 1 d D U P A 2
H11D H -0.453693 -0.204685 0.030369 0.144 Uiso 0.456(8) 1 calc R U P A 2
H11E H -0.484320 -0.428723 0.078135 0.144 Uiso 0.456(8) 1 calc R U P A 2
H11F H -0.181336 -0.278848 0.051245 0.144 Uiso 0.456(8) 1 calc R U P A 2


_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 C4 1.727(3) . ?
S1 C1 1.730(3) . ?
O1 C8 1.231(4) . ?
N1A C8 1.353(6) . ?
N1A C9A 1.468(7) . ?
N1A H1A 0.8800 . ?
N1B C8 1.352(7) . ?
N1B C9B 1.468(8) . ?
N1B H1B 0.8800 . ?
C1 C2 1.365(4) . ?
C1 C1 1.446(6) 2_776 ?
C2 C3 1.412(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.503(4) . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.518(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9A C10A 1.478(8) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9B C10B 1.476(9) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10A C11A 1.528(9) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10B C11B 1.526(10) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 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
C4 S1 C1 92.91(14) . . ?
C8 N1A C9A 125.9(7) . . ?
C8 N1A H1A 117.0 . . ?
C9A N1A H1A 117.0 . . ?
C8 N1B C9B 121.4(7) . . ?
C8 N1B H1B 119.3 . . ?
C9B N1B H1B 119.3 . . ?
C2 C1 C1 129.6(3) . 2_776 ?
C2 C1 S1 110.0(2) . . ?
C1 C1 S1 120.5(3) 2_776 . ?
C1 C2 C3 113.1(2) . . ?
C1 C2 H2 123.5 . . ?
C3 C2 H2 123.5 . . ?
C4 C3 C2 114.3(3) . . ?
C4 C3 H3 122.8 . . ?
C2 C3 H3 122.8 . . ?
C3 C4 C5 128.6(3) . . ?
C3 C4 S1 109.7(2) . . ?
C5 C4 S1 121.7(2) . . ?
C4 C5 C6 113.5(2) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 111.5(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 114.2(3) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1B 122.1(5) . . ?
O1 C8 N1A 121.1(5) . . ?
O1 C8 C7 122.3(3) . . ?
N1B C8 C7 113.8(5) . . ?
N1A C8 C7 115.6(4) . . ?
N1A C9A C10A 114.3(6) . . ?
N1A C9A H9AA 108.7 . . ?
C10A C9A H9AA 108.7 . . ?
N1A C9A H9AB 108.7 . . ?
C10A C9A H9AB 108.7 . . ?
H9AA C9A H9AB 107.6 . . ?
N1B C9B C10B 110.2(8) . . ?
N1B C9B H9BA 109.6 . . ?
C10B C9B H9BA 109.6 . . ?
N1B C9B H9BB 109.6 . . ?
C10B C9B H9BB 109.6 . . ?
H9BA C9B H9BB 108.1 . . ?
C9A C10A C11A 110.7(11) . . ?
C9A C10A H10A 109.5 . . ?
C11A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C11A C10A H10B 109.5 . . ?
H10A C10A H10B 108.1 . . ?
C9B C10B C11B 115.9(10) . . ?
C9B C10B H10C 108.3 . . ?
C11B C10B H10C 108.3 . . ?
C9B C10B H10D 108.3 . . ?
C11B C10B H10D 108.3 . . ?
H10C C10B H10D 107.4 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 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
C4 S1 C1 C2 0.1(2) . . . . ?
C4 S1 C1 C1 -179.4(3) . . . 2_776 ?
C1 C1 C2 C3 179.2(3) 2_776 . . . ?
S1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -179.5(3) . . . . ?
C2 C3 C4 S1 -0.2(3) . . . . ?
C1 S1 C4 C3 0.1(2) . . . . ?
C1 S1 C4 C5 179.4(2) . . . . ?
C3 C4 C5 C6 119.2(4) . . . . ?
S1 C4 C5 C6 -60.0(3) . . . . ?
C4 C5 C6 C7 -174.3(3) . . . . ?
C5 C6 C7 C8 179.4(3) . . . . ?
C9B N1B C8 O1 3.1(14) . . . . ?
C9B N1B C8 C7 168.3(8) . . . . ?
C9A N1A C8 O1 -9.2(11) . . . . ?
C9A N1A C8 C7 -178.2(7) . . . . ?
C6 C7 C8 O1 -25.0(6) . . . . ?
C6 C7 C8 N1B 169.9(6) . . . . ?
C6 C7 C8 N1A 143.8(5) . . . . ?
C8 N1A C9A C10A -120.7(10) . . . . ?
C8 N1B C9B C10B 124.8(11) . . . . ?
N1A C9A C10A C11A 176.4(10) . . . . ?
N1B C9B C10B C11B 173.5(15) . . . . ?

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.057

