# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
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data_111
_audit_block_doi                 10.5517/ccdc.csd.cc2969xr
_database_code_depnum_ccdc_archive 'CCDC 2121234'
loop_
_audit_author_name
_audit_author_address
'Weiguang Yang'
;Guangdong Medical University
China
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N3 O4 S'
_chemical_formula_sum            'C17 H17 N3 O4 S'
_chemical_formula_weight         359.39
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7875(5)
_cell_length_b                   8.8129(5)
_cell_length_c                   11.7354(6)
_cell_angle_alpha                93.835(2)
_cell_angle_beta                 111.598(2)
_cell_angle_gamma                96.227(2)
_cell_volume                     834.41(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      3.167
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0494 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17497
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3202
_reflns_number_total             3842
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1133
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C13(H13), C4(H4), C6(H6), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.32291(5) 0.83090(4) 0.31410(3) 0.04545(14) Uani 1 1 d . . . . .
O4 O 0.16821(14) 0.29000(11) -0.05570(10) 0.0446(3) Uani 1 1 d . . . . .
N3 N 0.32338(14) 0.58409(12) -0.07180(10) 0.0328(2) Uani 1 1 d . . . . .
O2 O 0.32679(17) 0.97473(13) 0.26692(12) 0.0579(3) Uani 1 1 d . . . . .
O3 O 0.13010(15) 0.38476(13) 0.11352(10) 0.0493(3) Uani 1 1 d . . . . .
O1 O 0.22347(18) 0.79441(17) 0.38350(12) 0.0639(4) Uani 1 1 d . . . . .
N1 N 0.25236(17) 0.69541(15) 0.19713(12) 0.0448(3) Uani 1 1 d . . . . .
H1 H 0.178148 0.624154 0.198427 0.054 Uiso 1 1 calc R . . . .
N2 N 0.38136(16) 0.79729(13) 0.06343(11) 0.0401(3) Uani 1 1 d . . . . .
C8 C 0.29864(17) 0.68254(16) 0.09636(12) 0.0353(3) Uani 1 1 d . . . . .
C15 C 0.18009(17) 0.40214(16) 0.03036(13) 0.0377(3) Uani 1 1 d . . . . .
C10 C 0.39513(17) 0.73657(15) -0.03973(13) 0.0347(3) Uani 1 1 d . . . . .
C5 C 0.5261(2) 0.80098(17) 0.39993(13) 0.0435(3) Uani 1 1 d . . . . .
C9 C 0.26019(17) 0.54743(16) 0.01743(12) 0.0349(3) Uani 1 1 d . . . . .
C11 C 0.46806(19) 0.80612(17) -0.11481(14) 0.0404(3) Uani 1 1 d . . . . .
H11 H 0.516080 0.908623 -0.095436 0.049 Uiso 1 1 calc R . . . .
C12 C 0.4677(2) 0.72179(18) -0.21636(14) 0.0442(3) Uani 1 1 d . . . . .
H12 H 0.516308 0.766685 -0.266516 0.053 Uiso 1 1 calc R . . . .
C14 C 0.32304(19) 0.49964(16) -0.17450(13) 0.0406(3) Uani 1 1 d . . . . .
H14 H 0.274407 0.397336 -0.194618 0.049 Uiso 1 1 calc R . . . .
C16 C 0.1002(2) 0.13716(16) -0.04354(15) 0.0450(4) Uani 1 1 d . . . . .
H16A H -0.013272 0.135183 -0.050012 0.054 Uiso 1 1 calc R . . . .
H16B H 0.164460 0.106080 0.035771 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3943(2) 0.56721(18) -0.24580(14) 0.0453(4) Uani 1 1 d . . . . .
H13 H 0.394831 0.510705 -0.315447 0.054 Uiso 1 1 calc R . . . .
C4 C 0.5544(3) 0.7141(2) 0.49728(15) 0.0565(4) Uani 1 1 d . . . . .
H4 H 0.467323 0.674231 0.518525 0.068 Uiso 1 1 calc R . . . .
C6 C 0.6554(2) 0.8607(2) 0.36835(16) 0.0554(4) Uani 1 1 d . . . . .
H6 H 0.636680 0.921259 0.303900 0.066 Uiso 1 1 calc R . . . .
C17 C 0.1079(3) 0.0317(2) -0.14619(18) 0.0576(4) Uani 1 1 d . . . . .
H17A H 0.042951 0.063161 -0.224025 0.086 Uiso 1 1 calc GR . . . .
H17B H 0.065004 -0.071518 -0.141157 0.086 Uiso 1 1 calc GR . . . .
H17C H 0.220643 0.035728 -0.139176 0.086 Uiso 1 1 calc GR . . . .
C3 C 0.7131(3) 0.6872(3) 0.56271(17) 0.0674(5) Uani 1 1 d . . . . .
H3 H 0.732615 0.630312 0.629355 0.081 Uiso 1 1 calc R . . . .
C7 C 0.8124(2) 0.8295(2) 0.43362(18) 0.0632(5) Uani 1 1 d . . . . .
H7 H 0.899069 0.867524 0.411267 0.076 Uiso 1 1 calc R . . . .
C2 C 0.8439(3) 0.7431(2) 0.53127(16) 0.0613(5) Uani 1 1 d . . . . .
C1 C 1.0172(3) 0.7102(3) 0.6013(2) 0.0932(8) Uani 1 1 d . . . . .
H1A H 1.014883 0.639543 0.659657 0.140 Uiso 1 1 calc GR . . . .
H1B H 1.086726 0.804242 0.644316 0.140 Uiso 1 1 calc GR . . . .
H1C H 1.060163 0.665995 0.544479 0.140 Uiso 1 1 calc GR . . . .


_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 O2 1.4188(13) . ?
S1 O1 1.4243(13) . ?
S1 N1 1.6394(13) . ?
S1 C5 1.7569(17) . ?
O4 C15 1.3319(18) . ?
O4 C16 1.4510(17) . ?
N3 C10 1.3852(17) . ?
N3 C9 1.3940(17) . ?
N3 C14 1.3724(18) . ?
O3 C15 1.2207(18) . ?
N1 H1 0.8600 . ?
N1 C8 1.3866(18) . ?
N2 C8 1.3418(18) . ?
N2 C10 1.3423(18) . ?
C8 C9 1.3874(19) . ?
C15 C9 1.4377(19) . ?
C10 C11 1.4020(19) . ?
C5 C4 1.379(2) . ?
C5 C6 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.405(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.348(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.498(2) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.378(3) . ?
C2 C1 1.512(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
O2 S1 O1 120.85(8) . . ?
O2 S1 N1 108.08(7) . . ?
O2 S1 C5 109.20(8) . . ?
O1 S1 N1 103.55(8) . . ?
O1 S1 C5 108.49(8) . . ?
N1 S1 C5 105.57(7) . . ?
C15 O4 C16 116.82(11) . . ?
C10 N3 C9 106.21(11) . . ?
C14 N3 C10 121.63(12) . . ?
C14 N3 C9 132.15(12) . . ?
S1 N1 H1 116.3 . . ?
C8 N1 S1 127.45(11) . . ?
C8 N1 H1 116.3 . . ?
C8 N2 C10 104.56(12) . . ?
N1 C8 C9 122.44(13) . . ?
N2 C8 N1 124.49(13) . . ?
N2 C8 C9 113.06(12) . . ?
O4 C15 C9 113.50(12) . . ?
O3 C15 O4 123.99(13) . . ?
O3 C15 C9 122.51(13) . . ?
N3 C10 C11 118.96(13) . . ?
N2 C10 N3 111.89(12) . . ?
N2 C10 C11 129.15(13) . . ?
C4 C5 S1 119.14(14) . . ?
C4 C5 C6 120.49(17) . . ?
C6 C5 S1 120.35(13) . . ?
N3 C9 C15 128.83(13) . . ?
C8 C9 N3 104.28(11) . . ?
C8 C9 C15 126.83(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.17(13) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.31(14) . . ?
C13 C12 H12 119.8 . . ?
N3 C14 H14 120.5 . . ?
C13 C14 N3 119.01(13) . . ?
C13 C14 H14 120.5 . . ?
O4 C16 H16A 110.4 . . ?
O4 C16 H16B 110.4 . . ?
O4 C16 C17 106.62(13) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.92(14) . . ?
C14 C13 H13 119.5 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.24(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.13(17) . . ?
C7 C6 H6 120.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C3 H3 119.3 . . ?
C4 C3 C2 121.33(18) . . ?
C2 C3 H3 119.3 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C2 121.49(19) . . ?
C2 C7 H7 119.3 . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C3 118.30(18) . . ?
C7 C2 C1 120.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
S1 N1 C8 N2 -16.2(2) . . . . ?
S1 N1 C8 C9 164.94(12) . . . . ?
S1 C5 C4 C3 178.33(14) . . . . ?
S1 C5 C6 C7 -176.98(14) . . . . ?
O4 C15 C9 N3 0.6(2) . . . . ?
O4 C15 C9 C8 -176.15(13) . . . . ?
N3 C10 C11 C12 -0.6(2) . . . . ?
N3 C14 C13 C12 -0.2(2) . . . . ?
O2 S1 N1 C8 45.84(15) . . . . ?
O2 S1 C5 C4 150.24(13) . . . . ?
O2 S1 C5 C6 -31.27(16) . . . . ?
O3 C15 C9 N3 179.86(14) . . . . ?
O3 C15 C9 C8 3.1(2) . . . . ?
O1 S1 N1 C8 175.15(13) . . . . ?
O1 S1 C5 C4 16.70(16) . . . . ?
O1 S1 C5 C6 -164.82(14) . . . . ?
N1 S1 C5 C4 -93.77(14) . . . . ?
N1 S1 C5 C6 84.72(14) . . . . ?
N1 C8 C9 N3 178.22(12) . . . . ?
N1 C8 C9 C15 -4.4(2) . . . . ?
N2 C8 C9 N3 -0.74(16) . . . . ?
N2 C8 C9 C15 176.65(13) . . . . ?
N2 C10 C11 C12 -179.89(15) . . . . ?
C8 N2 C10 N3 -0.58(16) . . . . ?
C8 N2 C10 C11 178.77(15) . . . . ?
C15 O4 C16 C17 -177.14(13) . . . . ?
C10 N3 C9 C8 0.34(14) . . . . ?
C10 N3 C9 C15 -176.98(14) . . . . ?
C10 N3 C14 C13 -0.1(2) . . . . ?
C10 N2 C8 N1 -178.11(13) . . . . ?
C10 N2 C8 C9 0.83(16) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C5 S1 N1 C8 -70.91(14) . . . . ?
C5 C4 C3 C2 -1.2(3) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
C9 N3 C10 N2 0.15(15) . . . . ?
C9 N3 C10 C11 -179.28(12) . . . . ?
C9 N3 C14 C13 179.57(14) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C14 N3 C10 N2 179.87(12) . . . . ?
C14 N3 C10 C11 0.4(2) . . . . ?
C14 N3 C9 C8 -179.34(14) . . . . ?
C14 N3 C9 C15 3.3(2) . . . . ?
C16 O4 C15 O3 -3.8(2) . . . . ?
C16 O4 C15 C9 175.44(12) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C4 C3 C2 C7 1.2(3) . . . . ?
C4 C3 C2 C1 -178.54(19) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C7 C2 C3 0.2(3) . . . . ?
C6 C7 C2 C1 179.93(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
