# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2131523'
loop_
_audit_author_name
_audit_author_address
'Xiao-Qiang Hu'
;South Central University for Nationalities
China
;
_audit_update_record             
;
2021-12-29 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.4931(9)
_cell_length_b                   9.7375(9)
_cell_length_c                   11.0376(9)
_cell_angle_alpha                89.373(2)
_cell_angle_beta                 73.867(2)
_cell_angle_gamma                62.537(2)
_cell_volume                     861.41(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3990
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.99

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18270
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.681
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_full        25.011
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3030
_reflns_number_gt                1881
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1018P)²+0.3257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.0816(6) 1.2787(5) 1.0036(5) 0.0946(14) Uani 1 1 d . . . . .
H1A H 0.0677 1.3159 1.0885 0.142 Uiso 1 1 calc R U . . .
H1B H -0.0211 1.2852 0.9998 0.142 Uiso 1 1 calc R U . . .
H1C H 0.1115 1.3417 0.9453 0.142 Uiso 1 1 calc R U . . .
C2 C 0.2182(5) 1.1105(4) 0.9679(4) 0.0652(10) Uani 1 1 d . . . . .
C3 C 0.2060(6) 0.9952(5) 1.0353(4) 0.0858(14) Uani 1 1 d . . . . .
H3 H 0.1117 1.0207 1.1044 0.103 Uiso 1 1 calc R U . . .
C4 C 0.3307(5) 0.8425(5) 1.0027(4) 0.0782(12) Uani 1 1 d . . . . .
H4 H 0.3199 0.7661 1.0496 0.094 Uiso 1 1 calc R U . . .
C5 C 0.4711(4) 0.8025(4) 0.9010(3) 0.0497(8) Uani 1 1 d . . . . .
C6 C 0.4834(5) 0.9170(5) 0.8325(4) 0.0704(11) Uani 1 1 d . . . . .
H6 H 0.5767 0.8920 0.7626 0.084 Uiso 1 1 calc R U . . .
C7 C 0.3575(5) 1.0685(5) 0.8674(4) 0.0768(12) Uani 1 1 d . . . . .
H7 H 0.3681 1.1451 0.8206 0.092 Uiso 1 1 calc R U . . .
C8 C 0.5015(5) 0.5554(4) 0.6910(3) 0.0617(10) Uani 1 1 d . . . . .
H8A H 0.5959 0.5439 0.6206 0.074 Uiso 1 1 calc R U . . .
H8B H 0.4170 0.6643 0.7075 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4322(4) 0.4561(4) 0.6547(3) 0.0517(9) Uani 1 1 d . . . . .
C10 C 0.5359(4) 0.3038(4) 0.5953(3) 0.0567(9) Uani 1 1 d . . . . .
H10 H 0.6501 0.2604 0.5816 0.068 Uiso 1 1 calc R U . . .
C11 C 0.4746(4) 0.2151(4) 0.5561(4) 0.0590(10) Uani 1 1 d . . . . .
H11 H 0.5469 0.1134 0.5155 0.071 Uiso 1 1 calc R U . . .
C12 C 0.3045(4) 0.2777(4) 0.5773(3) 0.0550(9) Uani 1 1 d . . . . .
C13 C 0.1985(4) 0.4269(4) 0.6394(4) 0.0623(10) Uani 1 1 d . . . . .
H13 H 0.0839 0.4691 0.6559 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2639(5) 0.5139(4) 0.6771(3) 0.0613(10) Uani 1 1 d . . . . .
H14 H 0.1914 0.6150 0.7191 0.074 Uiso 1 1 calc R U . . .
C15 C 0.0818(5) 0.2315(5) 0.5468(5) 0.0744(12) Uani 1 1 d . . . . .
H15 H 0.0195 0.3452 0.5504 0.089 Uiso 1 1 calc R U . . .
C16 C 0.0776(6) 0.1528(6) 0.4336(5) 0.0926(14) Uani 1 1 d . . . . .
H16A H 0.1214 0.1881 0.3579 0.139 Uiso 1 1 calc R U . . .
H16B H -0.0354 0.1780 0.4423 0.139 Uiso 1 1 calc R U . . .
H16C H 0.1441 0.0417 0.4277 0.139 Uiso 1 1 calc R U . . .
C17 C 0.0178(6) 0.1844(7) 0.6703(5) 0.1055(16) Uani 1 1 d . . . . .
H17A H 0.0805 0.0733 0.6669 0.158 Uiso 1 1 calc R U . . .
H17B H -0.0978 0.2141 0.6857 0.158 Uiso 1 1 calc R U . . .
H17C H 0.0295 0.2357 0.7378 0.158 Uiso 1 1 calc R U . . .
N1 N 0.5546(3) 0.5105(3) 0.8041(3) 0.0528(7) Uani 1 1 d . . . . .
H1 H 0.5462 0.4351 0.8406 0.063 Uiso 1 1 calc R U . . .
O1 O 0.6617(3) 0.5431(3) 0.9718(2) 0.0652(7) Uani 1 1 d . . . . .
O2 O 0.7637(3) 0.6021(3) 0.7571(2) 0.0646(7) Uani 1 1 d . . . . .
O3 O 0.2577(3) 0.1834(3) 0.5266(3) 0.0782(9) Uani 1 1 d . . . . .
S1 S 0.62949(10) 0.60665(10) 0.85839(8) 0.0528(3) Uani 1 1 d . . . . .


_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
C1 C2 1.514(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.357(5) . ?
C2 C3 1.371(6) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C5 S1 1.761(3) . ?
C6 C7 1.373(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.462(4) . ?
C8 C9 1.507(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.373(5) . ?
C9 C10 1.383(5) . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 O3 1.371(4) . ?
C12 C13 1.372(5) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.459(4) . ?
C15 C17 1.490(6) . ?
C15 C16 1.493(6) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 S1 1.613(3) . ?
N1 H1 0.8600 . ?
O1 S1 1.436(2) . ?
O2 S1 1.426(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.6(4) . . ?
C7 C2 C1 120.9(4) . . ?
C3 C2 C1 121.5(4) . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 S1 121.1(3) . . ?
C4 C5 S1 120.1(3) . . ?
C7 C6 C5 119.8(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C2 C7 C6 122.3(4) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
N1 C8 C9 111.2(3) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C14 C9 C10 117.3(3) . . ?
C14 C9 C8 121.4(3) . . ?
C10 C9 C8 121.3(3) . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O3 C12 C13 125.3(3) . . ?
O3 C12 C11 115.0(3) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 122.2(3) . . ?
C9 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
O3 C15 C17 107.7(4) . . ?
O3 C15 C16 105.4(3) . . ?
C17 C15 C16 114.3(4) . . ?
O3 C15 H15 109.8 . . ?
C17 C15 H15 109.8 . . ?
C16 C15 H15 109.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 N1 S1 118.1(2) . . ?
C8 N1 H1 120.9 . . ?
S1 N1 H1 120.9 . . ?
C12 O3 C15 120.8(3) . . ?
O2 S1 O1 119.13(15) . . ?
O2 S1 N1 107.95(15) . . ?
O1 S1 N1 105.64(14) . . ?
O2 S1 C5 107.72(15) . . ?
O1 S1 C5 108.75(15) . . ?
N1 S1 C5 107.08(15) . . ?

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
C7 C2 C3 C4 0.2(7) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C3 C4 C5 S1 -179.3(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
S1 C5 C6 C7 179.6(3) . . . . ?
C3 C2 C7 C6 0.1(7) . . . . ?
C1 C2 C7 C6 -179.9(4) . . . . ?
C5 C6 C7 C2 -0.7(7) . . . . ?
N1 C8 C9 C14 105.4(4) . . . . ?
N1 C8 C9 C10 -75.8(4) . . . . ?
C14 C9 C10 C11 2.2(5) . . . . ?
C8 C9 C10 C11 -176.6(3) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 O3 175.7(3) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
O3 C12 C13 C14 -174.9(3) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C10 C9 C14 C13 -1.8(5) . . . . ?
C8 C9 C14 C13 177.0(3) . . . . ?
C12 C13 C14 C9 -0.1(6) . . . . ?
C9 C8 N1 S1 -179.0(2) . . . . ?
C13 C12 O3 C15 -6.3(6) . . . . ?
C11 C12 O3 C15 177.1(3) . . . . ?
C17 C15 O3 C12 -85.8(4) . . . . ?
C16 C15 O3 C12 151.8(3) . . . . ?
C8 N1 S1 O2 -54.6(3) . . . . ?
C8 N1 S1 O1 177.0(2) . . . . ?
C8 N1 S1 C5 61.2(3) . . . . ?
C6 C5 S1 O2 5.8(4) . . . . ?
C4 C5 S1 O2 -175.6(3) . . . . ?
C6 C5 S1 O1 136.2(3) . . . . ?
C4 C5 S1 O1 -45.2(3) . . . . ?
C6 C5 S1 N1 -110.1(3) . . . . ?
C4 C5 S1 N1 68.5(3) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.049

