# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_reid001
_database_code_depnum_ccdc_archive 'CCDC 2149985'
loop_
_audit_author_name
_audit_author_address
'Junshan Lai'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_audit_creation_date             2022-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O2 S2'
_chemical_formula_sum            'C16 H17 N O2 S2'
_chemical_formula_weight         319.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.2635(5)
_cell_length_b                   11.4411(10)
_cell_length_c                   20.8675(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1495.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      67.78
_cell_measurement_theta_min      4.24
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0712 after correction.
The ratio of minimum to maximum transmission is 0.8821.
The λ/2 correction factor is not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.189
_diffrn_reflns_theta_min         4.237
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'cross coupled multi-layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microsource sealed X-ray tube'
_diffrn_source_current           0.59
_diffrn_source_power             0.0263612
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2604
_reflns_number_total             2735
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(7)
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.7576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06473(9) 0.24574(5) 0.67311(3) 0.01287(16) Uani 1 1 d . . . . .
S2 S 0.50595(10) 0.45536(6) 0.71370(3) 0.01870(17) Uani 1 1 d . . . . .
O1 O -0.1622(3) 0.24961(17) 0.68163(9) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.1734(3) 0.13576(15) 0.67265(9) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.1670(3) 0.32017(19) 0.73278(10) 0.0128(5) Uani 1 1 d . . . . .
C1 C 0.1239(4) 0.3186(2) 0.60120(12) 0.0136(6) Uani 1 1 d . . . . .
C2 C -0.0301(5) 0.3892(2) 0.57250(12) 0.0168(6) Uani 1 1 d . . . . .
H2 H -0.166417 0.398896 0.591763 0.020 Uiso 1 1 calc R U . . .
C3 C 0.0186(5) 0.4450(2) 0.51546(12) 0.0177(6) Uani 1 1 d . . . . .
H3 H -0.086051 0.492735 0.495450 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2190(5) 0.4324(2) 0.48677(13) 0.0180(6) Uani 1 1 d . . . . .
C5 C 0.3702(5) 0.3634(2) 0.51707(13) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.507988 0.355316 0.498555 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3241(5) 0.3058(2) 0.57396(13) 0.0168(6) Uani 1 1 d . . . . .
H6 H 0.428871 0.258098 0.593990 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2669(5) 0.4910(3) 0.42378(14) 0.0245(7) Uani 1 1 d . . . . .
H7A H 0.189525 0.450932 0.389359 0.037 Uiso 1 1 calc R U . . .
H7B H 0.420614 0.487208 0.415332 0.037 Uiso 1 1 calc R U . . .
H7C H 0.221610 0.572891 0.425655 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0924(4) 0.4415(2) 0.74315(13) 0.0160(6) Uani 1 1 d . . . . .
H8A H 0.088416 0.459108 0.789588 0.019 Uiso 1 1 calc R U . . .
H8B H -0.053476 0.451156 0.725664 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2455(4) 0.5244(2) 0.70944(14) 0.0169(6) Uani 1 1 d . . . . .
H9A H 0.247779 0.601337 0.731177 0.020 Uiso 1 1 calc R U . . .
H9B H 0.202171 0.536060 0.664258 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3979(4) 0.3150(2) 0.74300(12) 0.0136(6) Uani 1 1 d . . . . .
H10 H 0.457315 0.250786 0.715809 0.016 Uiso 1 1 calc R U . . .
C11 C 0.4507(4) 0.2883(2) 0.81296(12) 0.0137(6) Uani 1 1 d . . . . .
C12 C 0.6381(4) 0.3286(3) 0.84103(13) 0.0199(6) Uani 1 1 d . . . . .
H12 H 0.727661 0.380951 0.818068 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6955(5) 0.2933(3) 0.90222(14) 0.0240(7) Uani 1 1 d . . . . .
H13 H 0.824750 0.320621 0.920724 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5651(5) 0.2184(2) 0.93629(14) 0.0240(7) Uani 1 1 d . . . . .
H14 H 0.604653 0.194007 0.978158 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3765(5) 0.1790(2) 0.90920(14) 0.0219(7) Uani 1 1 d . . . . .
H15 H 0.285034 0.128651 0.932793 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3210(5) 0.2132(2) 0.84737(13) 0.0171(6) Uani 1 1 d . . . . .
H16 H 0.192958 0.184736 0.828653 0.020 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 O1 1.4334(18) . ?
S1 O2 1.4305(18) . ?
S1 N1 1.639(2) . ?
S1 C1 1.756(3) . ?
S2 C9 1.815(3) . ?
S2 C10 1.847(3) . ?
N1 C8 1.481(3) . ?
N1 C10 1.464(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 C5 1.386(4) . ?
C4 C7 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C11 1.528(3) . ?
C11 C12 1.391(4) . ?
C11 C16 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(4) . ?
C16 H16 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
O1 S1 N1 106.09(11) . . ?
O1 S1 C1 107.50(12) . . ?
O2 S1 O1 119.99(12) . . ?
O2 S1 N1 106.04(11) . . ?
O2 S1 C1 108.13(12) . . ?
N1 S1 C1 108.68(12) . . ?
C9 S2 C10 93.76(12) . . ?
C8 N1 S1 118.37(18) . . ?
C10 N1 S1 118.42(18) . . ?
C10 N1 C8 109.2(2) . . ?
C2 C1 S1 119.7(2) . . ?
C6 C1 S1 119.5(2) . . ?
C6 C1 C2 120.8(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 120.4(2) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 121.0(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
N1 C8 C9 108.6(2) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
S2 C9 H9A 110.6 . . ?
S2 C9 H9B 110.6 . . ?
C8 C9 S2 105.80(17) . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
S2 C10 H10 108.3 . . ?
N1 C10 S2 106.19(18) . . ?
N1 C10 H10 108.3 . . ?
N1 C10 C11 111.2(2) . . ?
C11 C10 S2 114.27(18) . . ?
C11 C10 H10 108.3 . . ?
C12 C11 C10 121.2(2) . . ?
C16 C11 C10 119.6(2) . . ?
C16 C11 C12 118.9(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

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
S1 N1 C8 C9 -94.7(2) . . . . ?
S1 N1 C10 S2 104.45(18) . . . . ?
S1 N1 C10 C11 -130.7(2) . . . . ?
S1 C1 C2 C3 -179.3(2) . . . . ?
S1 C1 C6 C5 179.9(2) . . . . ?
S2 C10 C11 C12 -30.5(3) . . . . ?
S2 C10 C11 C16 156.0(2) . . . . ?
O1 S1 N1 C8 -54.4(2) . . . . ?
O1 S1 N1 C10 169.79(19) . . . . ?
O1 S1 C1 C2 14.8(2) . . . . ?
O1 S1 C1 C6 -165.7(2) . . . . ?
O2 S1 N1 C8 176.93(18) . . . . ?
O2 S1 N1 C10 41.2(2) . . . . ?
O2 S1 C1 C2 145.7(2) . . . . ?
O2 S1 C1 C6 -34.8(3) . . . . ?
N1 S1 C1 C2 -99.6(2) . . . . ?
N1 S1 C1 C6 79.9(2) . . . . ?
N1 C8 C9 S2 -32.3(2) . . . . ?
N1 C10 C11 C12 -150.7(2) . . . . ?
N1 C10 C11 C16 35.8(3) . . . . ?
C1 S1 N1 C8 60.9(2) . . . . ?
C1 S1 N1 C10 -74.9(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C7 178.2(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C7 C4 C5 C6 -177.6(3) . . . . ?
C8 N1 C10 S2 -35.0(2) . . . . ?
C8 N1 C10 C11 89.8(3) . . . . ?
C9 S2 C10 N1 13.56(19) . . . . ?
C9 S2 C10 C11 -109.3(2) . . . . ?
C10 S2 C9 C8 10.47(19) . . . . ?
C10 N1 C8 C9 44.8(3) . . . . ?
C10 C11 C12 C13 -172.9(3) . . . . ?
C10 C11 C16 C15 174.0(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_original_sample_id jlai50-trip
_olex2_submission_special_instructions 'No special instructions were received'
