# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_zhou
_database_code_depnum_ccdc_archive 'CCDC 2224138'
loop_
_audit_author_name
_audit_author_address
Zhou
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H25 N O4 S'
_chemical_formula_sum            'C16 H25 N O4 S'
_chemical_formula_weight         327.43
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7519(8)
_cell_length_b                   17.4233(10)
_cell_length_c                   8.7618(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.248(7)
_cell_angle_gamma                90
_cell_volume                     1722.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12092
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.202
_cell_measurement_theta_min      3.367
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.202
_diffrn_reflns_theta_min         3.367
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'multiwire proportional'
_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             4095
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.052
_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)+(0.0472P)²+0.8641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1294
_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. Uiso/Uaniso restraints and constraints
Uanis(C00M) \\sim Ueq, Uanis(O006) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00E), C00G(H00G,H00H), C00H(H00I,H00J), C00I(H00K,H00L), C00K(H00P,
 H00Q)
3.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C008(H008), C00A(H00A), C00B(H00B), C00F(H00F)
3.d Idealised Me refined as rotating group:
 C00J(H00M,H00N,H00O), C00L(H00R,H00S,H00T), C00M(H00U,H00V,H00W)
;
_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
S01 S 0.44274(4) 0.37783(3) 0.92405(6) 0.03131(15) Uani 1 1 d . . . . .
O002 O 0.50673(13) 0.41105(9) 1.07428(16) 0.0398(4) Uani 1 1 d . . . . .
O003 O 0.37418(13) 0.31006(8) 0.92375(18) 0.0428(4) Uani 1 1 d . . . . .
O004 O 0.37314(15) 0.44138(9) 0.51827(19) 0.0476(4) Uani 1 1 d . . . . .
N005 N 0.35786(14) 0.44503(9) 0.83062(19) 0.0321(4) Uani 1 1 d . . . . .
H005 H 0.376696 0.490759 0.865586 0.039 Uiso 1 1 calc R U . . .
O006 O 0.18240(15) 0.39610(10) 0.4208(2) 0.0584(5) Uani 1 1 d . U . . .
C007 C 0.55126(17) 0.35591(11) 0.8256(2) 0.0303(4) Uani 1 1 d . . . . .
C008 C 0.56033(19) 0.28203(12) 0.7714(3) 0.0373(5) Uani 1 1 d . . . . .
H008 H 0.506025 0.244530 0.779560 0.045 Uiso 1 1 calc R U . . .
C009 C 0.25111(17) 0.43885(12) 0.6918(2) 0.0332(4) Uani 1 1 d . . . . .
C00A C 0.63047(19) 0.41207(12) 0.8102(3) 0.0388(5) Uani 1 1 d . . . . .
H00A H 0.623552 0.461776 0.845241 0.047 Uiso 1 1 calc R U . . .
C00B C 0.65125(19) 0.26473(13) 0.7050(3) 0.0408(5) Uani 1 1 d . . . . .
H00B H 0.657711 0.215106 0.669194 0.049 Uiso 1 1 calc R U . . .
C00C C 0.73257(19) 0.31963(13) 0.6907(3) 0.0399(5) Uani 1 1 d . . . . .
C00D C 0.28381(19) 0.39850(13) 0.5529(3) 0.0386(5) Uani 1 1 d . . . . .
H00D H 0.311977 0.346305 0.584010 0.046 Uiso 1 1 calc R U . . .
C00E C 0.2100(2) 0.52144(12) 0.6457(3) 0.0389(5) Uani 1 1 d . . . . .
H00C H 0.275457 0.550363 0.627185 0.047 Uiso 1 1 calc R U . . .
H00E H 0.146748 0.520542 0.547053 0.047 Uiso 1 1 calc R U . . .
C00F C 0.7198(2) 0.39384(13) 0.7426(3) 0.0434(5) Uani 1 1 d . . . . .
H00F H 0.772476 0.431831 0.731477 0.052 Uiso 1 1 calc R U . . .
C00G C 0.1518(2) 0.39496(14) 0.7360(3) 0.0473(6) Uani 1 1 d . . . . .
H00G H 0.084203 0.390480 0.642816 0.057 Uiso 1 1 calc R U . . .
H00H H 0.179059 0.343551 0.770178 0.057 Uiso 1 1 calc R U . . .
C00H C 0.1662(2) 0.56214(14) 0.7724(3) 0.0499(6) Uani 1 1 d . . . . .
H00I H 0.232654 0.570706 0.865493 0.060 Uiso 1 1 calc R U . . .
H00J H 0.134183 0.611836 0.732301 0.060 Uiso 1 1 calc R U . . .
C00I C 0.1133(2) 0.43467(17) 0.8678(3) 0.0607(7) Uani 1 1 d . . . . .
H00K H 0.179145 0.435864 0.963705 0.073 Uiso 1 1 calc R U . . .
H00L H 0.049322 0.405853 0.890579 0.073 Uiso 1 1 calc R U . . .
C00J C 0.8320(2) 0.29914(17) 0.6203(3) 0.0608(7) Uani 1 1 d . . . . .
H00M H 0.904288 0.293330 0.704126 0.091 Uiso 1 1 calc R U . . .
H00N H 0.841396 0.339223 0.549658 0.091 Uiso 1 1 calc R U . . .
H00O H 0.813641 0.251839 0.562494 0.091 Uiso 1 1 calc R U . . .
C00K C 0.0718(2) 0.51658(18) 0.8202(4) 0.0642(8) Uani 1 1 d . . . . .
H00P H 0.000280 0.515086 0.731947 0.077 Uiso 1 1 calc R U . . .
H00Q H 0.052958 0.541839 0.908744 0.077 Uiso 1 1 calc R U . . .
C00L C 0.4275(3) 0.40472(17) 0.4113(3) 0.0616(7) Uani 1 1 d . . . . .
H00R H 0.371626 0.401328 0.308003 0.092 Uiso 1 1 calc R U . . .
H00S H 0.452513 0.354068 0.449407 0.092 Uiso 1 1 calc R U . . .
H00T H 0.495061 0.434057 0.404459 0.092 Uiso 1 1 calc R U . . .
C00M C 0.1520(3) 0.3243(2) 0.3486(5) 0.1016(14) Uani 1 1 d . U . . .
H00U H 0.089533 0.330570 0.251758 0.152 Uiso 1 1 calc R U . . .
H00V H 0.125558 0.291192 0.419320 0.152 Uiso 1 1 calc R U . . .
H00W H 0.219962 0.302118 0.325276 0.152 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
S01 O002 1.4419(15) . ?
S01 O003 1.4290(15) . ?
S01 N005 1.6060(17) . ?
S01 C007 1.770(2) . ?
O004 C00D 1.389(3) . ?
O004 C00L 1.425(3) . ?
N005 H005 0.8600 . ?
N005 C009 1.487(3) . ?
O006 C00D 1.411(3) . ?
O006 C00M 1.402(3) . ?
C007 C008 1.386(3) . ?
C007 C00A 1.383(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.385(3) . ?
C009 C00D 1.544(3) . ?
C009 C00E 1.536(3) . ?
C009 C00G 1.533(3) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.379(3) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.382(3) . ?
C00C C00F 1.393(3) . ?
C00C C00J 1.509(3) . ?
C00D H00D 0.9800 . ?
C00E H00C 0.9700 . ?
C00E H00E 0.9700 . ?
C00E C00H 1.523(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00G C00I 1.520(4) . ?
C00H H00I 0.9700 . ?
C00H H00J 0.9700 . ?
C00H C00K 1.516(4) . ?
C00I H00K 0.9700 . ?
C00I H00L 0.9700 . ?
C00I C00K 1.528(4) . ?
C00J H00M 0.9600 . ?
C00J H00N 0.9600 . ?
C00J H00O 0.9600 . ?
C00K H00P 0.9700 . ?
C00K H00Q 0.9700 . ?
C00L H00R 0.9600 . ?
C00L H00S 0.9600 . ?
C00L H00T 0.9600 . ?
C00M H00U 0.9600 . ?
C00M H00V 0.9600 . ?
C00M H00W 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
O002 S01 N005 105.28(9) . . ?
O002 S01 C007 105.58(9) . . ?
O003 S01 O002 118.89(9) . . ?
O003 S01 N005 109.39(9) . . ?
O003 S01 C007 107.68(9) . . ?
N005 S01 C007 109.78(9) . . ?
C00D O004 C00L 114.08(19) . . ?
S01 N005 H005 115.6 . . ?
C009 N005 S01 128.73(14) . . ?
C009 N005 H005 115.6 . . ?
C00M O006 C00D 116.6(2) . . ?
C008 C007 S01 120.15(16) . . ?
C00A C007 S01 119.43(16) . . ?
C00A C007 C008 120.35(19) . . ?
C007 C008 H008 120.4 . . ?
C00B C008 C007 119.2(2) . . ?
C00B C008 H008 120.4 . . ?
N005 C009 C00D 109.79(16) . . ?
N005 C009 C00E 106.16(16) . . ?
N005 C009 C00G 110.93(17) . . ?
C00E C009 C00D 110.39(17) . . ?
C00G C009 C00D 110.32(18) . . ?
C00G C009 C00E 109.18(17) . . ?
C007 C00A H00A 120.2 . . ?
C00F C00A C007 119.5(2) . . ?
C00F C00A H00A 120.2 . . ?
C008 C00B H00B 119.3 . . ?
C00C C00B C008 121.4(2) . . ?
C00C C00B H00B 119.3 . . ?
C00B C00C C00F 118.2(2) . . ?
C00B C00C C00J 120.5(2) . . ?
C00F C00C C00J 121.3(2) . . ?
O004 C00D O006 110.67(19) . . ?
O004 C00D C009 107.30(17) . . ?
O004 C00D H00D 110.0 . . ?
O006 C00D C009 108.72(17) . . ?
O006 C00D H00D 110.0 . . ?
C009 C00D H00D 110.0 . . ?
C009 C00E H00C 109.0 . . ?
C009 C00E H00E 109.0 . . ?
H00C C00E H00E 107.8 . . ?
C00H C00E C009 112.95(18) . . ?
C00H C00E H00C 109.0 . . ?
C00H C00E H00E 109.0 . . ?
C00A C00F C00C 121.3(2) . . ?
C00A C00F H00F 119.4 . . ?
C00C C00F H00F 119.4 . . ?
C009 C00G H00G 109.2 . . ?
C009 C00G H00H 109.2 . . ?
H00G C00G H00H 107.9 . . ?
C00I C00G C009 112.0(2) . . ?
C00I C00G H00G 109.2 . . ?
C00I C00G H00H 109.2 . . ?
C00E C00H H00I 109.1 . . ?
C00E C00H H00J 109.1 . . ?
H00I C00H H00J 107.9 . . ?
C00K C00H C00E 112.4(2) . . ?
C00K C00H H00I 109.1 . . ?
C00K C00H H00J 109.1 . . ?
C00G C00I H00K 109.4 . . ?
C00G C00I H00L 109.4 . . ?
C00G C00I C00K 111.0(2) . . ?
H00K C00I H00L 108.0 . . ?
C00K C00I H00K 109.4 . . ?
C00K C00I H00L 109.4 . . ?
C00C C00J H00M 109.5 . . ?
C00C C00J H00N 109.5 . . ?
C00C C00J H00O 109.5 . . ?
H00M C00J H00N 109.5 . . ?
H00M C00J H00O 109.5 . . ?
H00N C00J H00O 109.5 . . ?
C00H C00K C00I 111.2(2) . . ?
C00H C00K H00P 109.4 . . ?
C00H C00K H00Q 109.4 . . ?
C00I C00K H00P 109.4 . . ?
C00I C00K H00Q 109.4 . . ?
H00P C00K H00Q 108.0 . . ?
O004 C00L H00R 109.5 . . ?
O004 C00L H00S 109.5 . . ?
O004 C00L H00T 109.5 . . ?
H00R C00L H00S 109.5 . . ?
H00R C00L H00T 109.5 . . ?
H00S C00L H00T 109.5 . . ?
O006 C00M H00U 109.5 . . ?
O006 C00M H00V 109.5 . . ?
O006 C00M H00W 109.5 . . ?
H00U C00M H00V 109.5 . . ?
H00U C00M H00W 109.5 . . ?
H00V C00M H00W 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
S01 N005 C009 C00D -57.2(2) . . . . ?
S01 N005 C009 C00E -176.50(14) . . . . ?
S01 N005 C009 C00G 65.0(2) . . . . ?
S01 C007 C008 C00B -175.38(16) . . . . ?
S01 C007 C00A C00F 175.90(16) . . . . ?
O002 S01 N005 C009 -162.09(16) . . . . ?
O002 S01 C007 C008 125.19(17) . . . . ?
O002 S01 C007 C00A -51.66(18) . . . . ?
O003 S01 N005 C009 -33.25(19) . . . . ?
O003 S01 C007 C008 -2.79(19) . . . . ?
O003 S01 C007 C00A -179.63(16) . . . . ?
N005 S01 C007 C008 -121.80(17) . . . . ?
N005 S01 C007 C00A 61.36(18) . . . . ?
N005 C009 C00D O004 -57.9(2) . . . . ?
N005 C009 C00D O006 -177.65(17) . . . . ?
N005 C009 C00E C00H -66.1(2) . . . . ?
N005 C009 C00G C00I 60.5(2) . . . . ?
C007 S01 N005 C009 84.70(18) . . . . ?
C007 C008 C00B C00C -0.4(3) . . . . ?
C007 C00A C00F C00C -0.6(3) . . . . ?
C008 C007 C00A C00F -0.9(3) . . . . ?
C008 C00B C00C C00F -1.1(3) . . . . ?
C008 C00B C00C C00J 179.0(2) . . . . ?
C009 C00E C00H C00K -53.1(3) . . . . ?
C009 C00G C00I C00K 57.8(3) . . . . ?
C00A C007 C008 C00B 1.4(3) . . . . ?
C00B C00C C00F C00A 1.6(3) . . . . ?
C00D C009 C00E C00H 174.98(18) . . . . ?
C00D C009 C00G C00I -177.6(2) . . . . ?
C00E C009 C00D O004 58.8(2) . . . . ?
C00E C009 C00D O006 -60.9(2) . . . . ?
C00E C009 C00G C00I -56.1(3) . . . . ?
C00E C00H C00K C00I 52.8(3) . . . . ?
C00G C009 C00D O004 179.52(17) . . . . ?
C00G C009 C00D O006 59.8(2) . . . . ?
C00G C009 C00E C00H 53.5(2) . . . . ?
C00G C00I C00K C00H -55.1(3) . . . . ?
C00J C00C C00F C00A -178.5(2) . . . . ?
C00L O004 C00D O006 -71.9(2) . . . . ?
C00L O004 C00D C009 169.66(19) . . . . ?
C00M O006 C00D O004 113.7(3) . . . . ?
C00M O006 C00D C009 -128.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
