# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_s_0m
_database_code_depnum_ccdc_archive 'CCDC 2244430'
loop_
_audit_author_name
_audit_author_address
'Juan Liu'
;China Agricultural University
China
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2023-02-24
_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         'C16 H19 N O4 S'
_chemical_formula_sum            'C16 H19 N O4 S'
_chemical_formula_weight         321.38
_chemical_absolute_configuration rmad
_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                   7.54870(10)
_cell_length_b                   11.1741(2)
_cell_length_c                   18.1225(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1528.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8900
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.457
_cell_measurement_theta_min      2.438
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.1163
_exptl_absorpt_correction_T_min  0.0175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1143 before and 0.0713 after correction. The Ratio of minimum to maximum transmission is 0.1505. 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    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10288
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.450
_diffrn_reflns_theta_min         4.649
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2991
_reflns_number_total             3070
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.089
_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)+(0.0659P)²+0.0835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1110
_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, All O(H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C16(H16), C12(H12), C4(H4A), C14(H14), C13(H13), C7(H7),
 C3(H3A)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 0.82515(8) 0.46764(6) 0.47165(3) 0.0406(2) Uani 1 1 d . . . . .
O4 O 0.4303(3) 0.75397(17) 0.41578(12) 0.0460(4) Uani 1 1 d . . . . .
H4 H 0.534805 0.779735 0.415065 0.069 Uiso 1 1 calc GR . . . .
O1 O 0.7442(3) 0.39993(19) 0.41366(12) 0.0493(5) Uani 1 1 d . . . . .
O2 O 1.0002(3) 0.51727(19) 0.46100(12) 0.0485(5) Uani 1 1 d . . . . .
O3 O 0.2387(3) 0.63793(18) 0.54787(12) 0.0477(5) Uani 1 1 d . . . . .
H3 H 0.197262 0.574322 0.530216 0.072 Uiso 1 1 calc GR . . . .
N1 N 0.6994(3) 0.5815(2) 0.48813(12) 0.0395(5) Uani 1 1 d D . . . .
C5 C 0.8352(4) 0.3749(2) 0.55024(15) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.9326(4) 0.4114(3) 0.61120(16) 0.0464(6) Uani 1 1 d . . . . .
H6 H 0.988717 0.487466 0.611473 0.056 Uiso 1 1 calc R . . . .
C11 C 0.4748(3) 0.5597(2) 0.62437(15) 0.0417(6) Uani 1 1 d . . . . .
C9 C 0.4321(4) 0.6268(3) 0.41425(16) 0.0439(6) Uani 1 1 d . . . . .
H9A H 0.505092 0.599883 0.372016 0.053 Uiso 1 1 calc R . . . .
H9B H 0.309816 0.597534 0.406208 0.053 Uiso 1 1 calc R . . . .
C15 C 0.6130(5) 0.5534(3) 0.74436(17) 0.0548(7) Uani 1 1 d . . . . .
H15 H 0.681804 0.591004 0.781640 0.066 Uiso 1 1 calc R . . . .
C10 C 0.4272(4) 0.6272(2) 0.55501(15) 0.0402(5) Uani 1 1 d . . . . .
H10 H 0.476951 0.709770 0.559568 0.048 Uiso 1 1 calc R . . . .
C16 C 0.5772(4) 0.6131(3) 0.67891(16) 0.0469(6) Uani 1 1 d . . . . .
H16 H 0.623040 0.691339 0.671307 0.056 Uiso 1 1 calc R . . . .
C12 C 0.4126(4) 0.4442(3) 0.63578(17) 0.0489(6) Uani 1 1 d . . . . .
H12 H 0.344127 0.406042 0.598607 0.059 Uiso 1 1 calc R . . . .
C4 C 0.7497(4) 0.2647(3) 0.55020(17) 0.0457(6) Uani 1 1 d . . . . .
H4A H 0.682400 0.239923 0.508623 0.055 Uiso 1 1 calc R . . . .
C14 C 0.5482(5) 0.4389(3) 0.75512(19) 0.0580(8) Uani 1 1 d . . . . .
H14 H 0.571965 0.398149 0.800057 0.070 Uiso 1 1 calc R . . . .
C13 C 0.4497(5) 0.3837(3) 0.70112(19) 0.0566(8) Uani 1 1 d . . . . .
H13 H 0.407096 0.304547 0.708394 0.068 Uiso 1 1 calc R . . . .
C7 C 0.9475(4) 0.3362(3) 0.67157(17) 0.0485(6) Uani 1 1 d . . . . .
H7 H 1.015211 0.360972 0.713032 0.058 Uiso 1 1 calc R . . . .
C8 C 0.5051(4) 0.5709(2) 0.48517(14) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.474151 0.483879 0.485069 0.047 Uiso 1 1 calc R . . . .
C2 C 0.8646(4) 0.2244(3) 0.67251(17) 0.0455(6) Uani 1 1 d . . . . .
C1 C 0.8823(5) 0.1441(3) 0.7387(2) 0.0581(8) Uani 1 1 d . . . . .
H1A H 1.005921 0.118539 0.743791 0.087 Uiso 1 1 calc GR . . . .
H1B H 0.806457 0.073680 0.732390 0.087 Uiso 1 1 calc GR . . . .
H1C H 0.846178 0.187764 0.783146 0.087 Uiso 1 1 calc GR . . . .
C3 C 0.7641(4) 0.1914(3) 0.61163(17) 0.0479(6) Uani 1 1 d . . . . .
H3A H 0.703716 0.116835 0.612096 0.057 Uiso 1 1 calc R . . . .
H1 H 0.752(5) 0.639(3) 0.5101(18) 0.048(9) Uiso 1 1 d 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
S1 O1 1.432(2) . ?
S1 O2 1.446(2) . ?
S1 N1 1.615(2) . ?
S1 C5 1.763(3) . ?
O4 H4 0.8400 . ?
O4 C9 1.421(4) . ?
O3 H3 0.8400 . ?
O3 C10 1.433(3) . ?
N1 C8 1.472(3) . ?
N1 H1 0.86(2) . ?
C5 C6 1.388(4) . ?
C5 C4 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(4) . ?
C11 C10 1.509(4) . ?
C11 C16 1.390(4) . ?
C11 C12 1.389(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.532(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(5) . ?
C15 C14 1.384(6) . ?
C10 H10 1.0000 . ?
C10 C8 1.531(4) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.392(5) . ?
C4 H4A 0.9500 . ?
C4 C3 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.375(6) . ?
C13 H13 0.9500 . ?
C7 H7 0.9500 . ?
C7 C2 1.397(4) . ?
C8 H8 1.0000 . ?
C2 C1 1.505(4) . ?
C2 C3 1.389(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 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 O2 119.64(13) . . ?
O1 S1 N1 107.53(13) . . ?
O1 S1 C5 107.50(13) . . ?
O2 S1 N1 105.06(12) . . ?
O2 S1 C5 107.10(13) . . ?
N1 S1 C5 109.80(12) . . ?
C9 O4 H4 109.5 . . ?
C10 O3 H3 109.5 . . ?
S1 N1 H1 114(3) . . ?
C8 N1 S1 121.03(19) . . ?
C8 N1 H1 123(3) . . ?
C6 C5 S1 119.6(2) . . ?
C6 C5 C4 120.4(3) . . ?
C4 C5 S1 120.0(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C16 C11 C10 120.6(2) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 C16 118.8(3) . . ?
O4 C9 H9A 108.9 . . ?
O4 C9 H9B 108.9 . . ?
O4 C9 C8 113.3(2) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
O3 C10 C11 110.7(2) . . ?
O3 C10 H10 107.6 . . ?
O3 C10 C8 110.0(2) . . ?
C11 C10 H10 107.6 . . ?
C11 C10 C8 113.1(2) . . ?
C8 C10 H10 107.6 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4A 120.4 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C2 121.1(3) . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C9 110.9(2) . . ?
N1 C8 C10 108.7(2) . . ?
N1 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C10 C8 C9 112.8(2) . . ?
C10 C8 H8 108.1 . . ?
C7 C2 C1 120.2(3) . . ?
C3 C2 C7 118.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
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 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
