# 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. 
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data_cxy3456_0m
_database_code_depnum_ccdc_archive 'CCDC 2131923'
loop_
_audit_author_name
_audit_author_address
Zhang
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O S'
_chemical_formula_sum            'C17 H19 N O S'
_chemical_formula_weight         285.39
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8663(14)
_cell_length_b                   8.7930(14)
_cell_length_c                   10.1594(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.871(5)
_cell_angle_gamma                90
_cell_volume                     749.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9809
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      4.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.865
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0775 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8608.
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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11797
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.437
_diffrn_reflns_theta_min         4.599
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2726
_reflns_number_total             2740
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_coef       0.0257(19)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.1808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
  C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.51383(5) 0.56709(6) 0.75496(5) 0.01738(16) Uani 1 1 d . . . . .
O1 O 0.57963(16) 0.61320(16) 0.11426(14) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.45241(19) 0.3889(2) 0.04333(17) 0.0139(4) Uani 1 1 d . . . . .
H1 H 0.463826 0.290582 0.033180 0.017 Uiso 1 1 calc R U . . .
C1 C -0.0128(2) 0.5660(3) -0.0872(2) 0.0285(5) Uani 1 1 d . . . . .
H1A H -0.118000 0.605922 -0.116989 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0374(3) 0.4721(3) -0.1744(2) 0.0248(5) Uani 1 1 d . . . . .
H2 H -0.034067 0.447311 -0.263874 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1916(2) 0.4138(3) -0.1320(2) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.225733 0.349618 -0.192079 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2956(2) 0.4505(2) -0.0004(2) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.5848(2) 0.4738(2) 0.09970(19) 0.0121(4) Uani 1 1 d . . . . .
C6 C 0.7417(2) 0.3894(2) 0.14522(19) 0.0138(4) Uani 1 1 d . . . . .
H6A H 0.795305 0.401517 0.074193 0.017 Uiso 1 1 calc R U . . .
H6B H 0.722112 0.279620 0.154134 0.017 Uiso 1 1 calc R U . . .
C7 C 0.8503(2) 0.4517(2) 0.2864(2) 0.0139(4) Uani 1 1 d . . . . .
H7 H 0.861106 0.564031 0.276622 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7749(2) 0.4249(2) 0.3976(2) 0.0143(4) Uani 1 1 d . . . . .
H8 H 0.763988 0.322698 0.423399 0.017 Uiso 1 1 calc R U . . .
C9 C 0.7223(2) 0.5344(2) 0.46238(19) 0.0150(4) Uani 1 1 d . . . . .
H9 H 0.733428 0.636248 0.435791 0.018 Uiso 1 1 calc R U . . .
C10 C 0.6487(2) 0.5115(2) 0.5711(2) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.6237(2) 0.3682(2) 0.6279(2) 0.0158(4) Uani 1 1 d . . . . .
H11 H 0.654392 0.273580 0.599223 0.019 Uiso 1 1 calc R U . . .
C12 C 0.5520(2) 0.3810(3) 0.7267(2) 0.0177(4) Uani 1 1 d . . . . .
H12 H 0.526045 0.297214 0.774331 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5957(2) 0.6291(3) 0.6332(2) 0.0170(4) Uani 1 1 d . . . . .
H13 H 0.603455 0.733227 0.611162 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0176(2) 0.3815(3) 0.3267(2) 0.0167(4) Uani 1 1 d . . . . .
H14A H 1.012616 0.274212 0.354674 0.020 Uiso 1 1 calc R U . . .
H14B H 1.055274 0.382585 0.245005 0.020 Uiso 1 1 calc R U . . .
C15 C 1.1357(2) 0.4683(3) 0.4462(2) 0.0246(5) Uani 1 1 d . . . . .
H15A H 1.139534 0.574860 0.419286 0.037 Uiso 1 1 calc R U . . .
H15B H 1.241836 0.422841 0.467262 0.037 Uiso 1 1 calc R U . . .
H15C H 1.101575 0.462800 0.528670 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2449(2) 0.5429(2) 0.0881(2) 0.0195(5) Uani 1 1 d . . . . .
H16 H 0.315076 0.566023 0.178493 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0910(3) 0.6014(3) 0.0436(3) 0.0256(5) Uani 1 1 d . . . . .
H17 H 0.056794 0.666116 0.103314 0.031 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 C12 1.714(2) . ?
S1 C13 1.713(2) . ?
O1 C5 1.237(3) . ?
N1 H1 0.8800 . ?
N1 C4 1.423(3) . ?
N1 C5 1.352(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(4) . ?
C1 C17 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C4 C16 1.390(3) . ?
C5 C6 1.511(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.547(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.506(3) . ?
C7 C14 1.535(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.332(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.467(3) . ?
C10 C11 1.433(3) . ?
C10 C13 1.371(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.355(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.526(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 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
C13 S1 C12 91.73(10) . . ?
C4 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
C5 N1 C4 123.25(17) . . ?
C2 C1 H1A 120.1 . . ?
C2 C1 C17 119.77(19) . . ?
C17 C1 H1A 120.1 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 N1 119.18(19) . . ?
C16 C4 N1 120.57(18) . . ?
C16 C4 C3 120.24(19) . . ?
O1 C5 N1 122.52(19) . . ?
O1 C5 C6 121.05(19) . . ?
N1 C5 C6 116.43(18) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.20(16) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7 108.0 . . ?
C8 C7 C6 110.22(16) . . ?
C8 C7 H7 108.0 . . ?
C8 C7 C14 111.23(16) . . ?
C14 C7 C6 111.29(16) . . ?
C14 C7 H7 108.0 . . ?
C7 C8 H8 117.7 . . ?
C9 C8 C7 124.67(19) . . ?
C9 C8 H8 117.7 . . ?
C8 C9 H9 117.1 . . ?
C8 C9 C10 125.80(19) . . ?
C10 C9 H9 117.1 . . ?
C11 C10 C9 126.01(19) . . ?
C13 C10 C9 123.03(19) . . ?
C13 C10 C11 110.96(18) . . ?
C10 C11 H11 123.3 . . ?
C12 C11 C10 113.30(19) . . ?
C12 C11 H11 123.3 . . ?
S1 C12 H12 124.2 . . ?
C11 C12 S1 111.66(16) . . ?
C11 C12 H12 124.2 . . ?
S1 C13 H13 123.8 . . ?
C10 C13 S1 112.34(17) . . ?
C10 C13 H13 123.8 . . ?
C7 C14 H14A 109.3 . . ?
C7 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C7 111.47(18) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16 120.2 . . ?
C17 C16 C4 119.7(2) . . ?
C17 C16 H16 120.2 . . ?
C1 C17 C16 120.4(2) . . ?
C1 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?

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
O1 C5 C6 C7 41.3(3) . . . . ?
N1 C4 C16 C17 -179.70(19) . . . . ?
N1 C5 C6 C7 -138.55(17) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C17 C16 -0.2(3) . . . . ?
C2 C3 C4 N1 179.10(19) . . . . ?
C2 C3 C4 C16 0.8(3) . . . . ?
C3 C4 C16 C17 -1.4(3) . . . . ?
C4 N1 C5 O1 -1.9(3) . . . . ?
C4 N1 C5 C6 177.88(17) . . . . ?
C4 C16 C17 C1 1.1(3) . . . . ?
C5 N1 C4 C3 131.2(2) . . . . ?
C5 N1 C4 C16 -50.5(3) . . . . ?
C5 C6 C7 C8 62.9(2) . . . . ?
C5 C6 C7 C14 -173.21(16) . . . . ?
C6 C7 C8 C9 -113.3(2) . . . . ?
C6 C7 C14 C15 166.48(18) . . . . ?
C7 C8 C9 C10 -179.87(17) . . . . ?
C8 C7 C14 C15 -70.2(2) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C8 C9 C10 C13 -179.4(2) . . . . ?
C9 C10 C11 C12 -179.57(18) . . . . ?
C9 C10 C13 S1 179.42(14) . . . . ?
C10 C11 C12 S1 -0.5(2) . . . . ?
C11 C10 C13 S1 -1.2(2) . . . . ?
C12 S1 C13 C10 0.83(16) . . . . ?
C13 S1 C12 C11 -0.19(17) . . . . ?
C13 C10 C11 C12 1.1(3) . . . . ?
C14 C7 C8 C9 122.8(2) . . . . ?
C17 C1 C2 C3 -0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
