# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ss_ps2450_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2333703'
loop_
_audit_author_name
_audit_author_address
'Swati Singh'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2023-09-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O4 S'
_chemical_formula_sum            'C18 H21 N O4 S'
_chemical_formula_weight         347.42
_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                   14.641(3)
_cell_length_b                   10.835(2)
_cell_length_c                   12.117(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.599(8)
_cell_angle_gamma                90
_cell_volume                     1832.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34644
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.380
_diffrn_ambient_temperature      303.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2820
_reflns_number_total             3752
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.018
_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)+(0.0582P)²+0.4341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.14479(3) 0.68319(4) 0.58145(4) 0.05394(17) Uani 1 1 d . . . . .
O1 O 0.04377(9) 0.68423(14) 0.52139(12) 0.0701(4) Uani 1 1 d . . . . .
O2 O 0.18989(10) 0.79831(12) 0.62817(13) 0.0661(4) Uani 1 1 d . . . . .
O3 O 0.14393(10) 0.44313(12) 0.21582(11) 0.0611(4) Uani 1 1 d . . . . .
O4 O 0.50282(11) 0.58873(18) 0.65403(15) 0.0958(6) Uani 1 1 d . . . . .
N1 N 0.36032(11) 0.68717(15) 0.61568(14) 0.0605(4) Uani 1 1 d . . . . .
H1 H 0.331155 0.745030 0.640122 0.073 Uiso 1 1 calc R U . . .
C1 C 0.16725(13) 0.57561(17) 0.69520(15) 0.0515(4) Uani 1 1 d . . . . .
C2 C 0.20905(15) 0.6113(2) 0.80824(17) 0.0672(6) Uani 1 1 d . . . . .
H2 H 0.230047 0.692084 0.825423 0.081 Uiso 1 1 calc R U . . .
C3 C 0.21950(17) 0.5261(2) 0.89583(19) 0.0746(6) Uani 1 1 d . . . . .
H3 H 0.246536 0.551191 0.972189 0.090 Uiso 1 1 calc R U . . .
C4 C 0.19106(16) 0.4049(2) 0.87358(18) 0.0662(5) Uani 1 1 d . . . . .
C5 C 0.15148(16) 0.3709(2) 0.75839(19) 0.0712(6) Uani 1 1 d . . . . .
H5 H 0.133161 0.289276 0.740847 0.085 Uiso 1 1 calc R U . . .
C6 C 0.13872(15) 0.45400(19) 0.67016(18) 0.0633(5) Uani 1 1 d . . . . .
H6 H 0.111102 0.429215 0.593833 0.076 Uiso 1 1 calc R U . . .
C7 C 0.20469(13) 0.61954(16) 0.48800(15) 0.0491(4) Uani 1 1 d . . . . .
C8 C 0.14796(13) 0.56210(16) 0.38751(15) 0.0508(4) Uani 1 1 d . . . . .
H8 H 0.081530 0.563490 0.369167 0.061 Uiso 1 1 calc R U . . .
C9 C 0.19139(13) 0.50322(16) 0.31563(15) 0.0505(4) Uani 1 1 d . . . . .
C10 C 0.29056(14) 0.50236(18) 0.34535(16) 0.0561(5) Uani 1 1 d . . . . .
H10 H 0.320025 0.461791 0.297601 0.067 Uiso 1 1 calc R U . . .
C11 C 0.34633(14) 0.55995(19) 0.44357(16) 0.0567(5) Uani 1 1 d . . . . .
H11 H 0.412699 0.557684 0.461145 0.068 Uiso 1 1 calc R U . . .
C12 C 0.30487(13) 0.62184(17) 0.51738(15) 0.0502(4) Uani 1 1 d . . . . .
C13 C 0.1995(2) 0.3132(3) 0.9692(2) 0.0943(8) Uani 1 1 d . . . . .
H13A H 0.243248 0.248955 0.964325 0.141 Uiso 1 1 calc R U . . .
H13B H 0.137691 0.278040 0.961564 0.141 Uiso 1 1 calc R U . . .
H13C H 0.222863 0.354029 1.042662 0.141 Uiso 1 1 calc R U . . .
C14 C 0.04285(16) 0.4576(2) 0.1730(2) 0.0800(7) Uani 1 1 d . . . . .
H14A H 0.019186 0.417768 0.099023 0.120 Uiso 1 1 calc R U . . .
H14B H 0.027332 0.543908 0.164666 0.120 Uiso 1 1 calc R U . . .
H14C H 0.013752 0.421058 0.226229 0.120 Uiso 1 1 calc R U . . .
C15 C 0.45400(15) 0.6701(2) 0.67651(19) 0.0688(6) Uani 1 1 d . . . . .
C16 C 0.49413(17) 0.7592(3) 0.7767(2) 0.0878(8) Uani 1 1 d . . . . .
H16 H 0.446470 0.823517 0.774049 0.105 Uiso 1 1 calc R U . . .
C17 C 0.5127(3) 0.6881(4) 0.8889(2) 0.1314(13) Uani 1 1 d . . . . .
H17A H 0.540923 0.742078 0.952986 0.197 Uiso 1 1 calc R U . . .
H17B H 0.555759 0.621027 0.889637 0.197 Uiso 1 1 calc R U . . .
H17C H 0.453369 0.656157 0.895181 0.197 Uiso 1 1 calc R U . . .
C18 C 0.5848(2) 0.8191(3) 0.7662(3) 0.1146(11) Uani 1 1 d . . . . .
H18A H 0.610081 0.874459 0.830046 0.172 Uiso 1 1 calc R U . . .
H18B H 0.570368 0.864252 0.694861 0.172 Uiso 1 1 calc R U . . .
H18C H 0.631432 0.756447 0.767156 0.172 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 O1 1.4374(14) . ?
S1 O2 1.4444(14) . ?
S1 C1 1.759(2) . ?
S1 C7 1.7685(18) . ?
O3 C9 1.364(2) . ?
O3 C14 1.421(2) . ?
O4 C15 1.217(2) . ?
N1 H1 0.8600 . ?
N1 C12 1.412(2) . ?
N1 C15 1.359(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 C5 1.390(3) . ?
C4 C13 1.503(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(2) . ?
C7 C12 1.401(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 C10 1.386(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.523(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.513(4) . ?
C16 C18 1.518(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O1 S1 O2 118.04(8) . . ?
O1 S1 C1 108.79(9) . . ?
O1 S1 C7 108.20(8) . . ?
O2 S1 C1 108.08(9) . . ?
O2 S1 C7 109.34(9) . . ?
C1 S1 C7 103.41(8) . . ?
C9 O3 C14 117.79(15) . . ?
C12 N1 H1 115.9 . . ?
C15 N1 H1 115.9 . . ?
C15 N1 C12 128.15(17) . . ?
C2 C1 S1 121.01(15) . . ?
C2 C1 C6 119.90(19) . . ?
C6 C1 S1 119.04(14) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 C13 122.0(2) . . ?
C5 C4 C13 120.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.58(19) . . ?
C5 C6 H6 120.2 . . ?
C8 C7 S1 116.93(14) . . ?
C8 C7 C12 122.05(16) . . ?
C12 C7 S1 120.94(13) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.37(17) . . ?
C9 C8 H8 120.3 . . ?
O3 C9 C8 124.87(17) . . ?
O3 C9 C10 116.09(16) . . ?
C8 C9 C10 119.03(17) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.59(17) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.94(18) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 N1 120.92(16) . . ?
C11 C12 N1 122.07(17) . . ?
C11 C12 C7 116.98(17) . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 N1 122.8(2) . . ?
O4 C15 C16 121.8(2) . . ?
N1 C15 C16 115.40(18) . . ?
C15 C16 H16 109.0 . . ?
C17 C16 C15 108.4(2) . . ?
C17 C16 H16 109.0 . . ?
C17 C16 C18 111.6(2) . . ?
C18 C16 C15 109.9(2) . . ?
C18 C16 H16 109.0 . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C1 C2 C3 175.53(17) . . . . ?
S1 C1 C6 C5 -176.76(16) . . . . ?
S1 C7 C8 C9 -175.43(14) . . . . ?
S1 C7 C12 N1 -7.3(2) . . . . ?
S1 C7 C12 C11 174.48(14) . . . . ?
O1 S1 C1 C2 -120.82(16) . . . . ?
O1 S1 C1 C6 56.64(17) . . . . ?
O1 S1 C7 C8 -11.66(17) . . . . ?
O1 S1 C7 C12 171.44(15) . . . . ?
O2 S1 C1 C2 8.48(18) . . . . ?
O2 S1 C1 C6 -174.06(15) . . . . ?
O2 S1 C7 C8 -141.45(14) . . . . ?
O2 S1 C7 C12 41.65(17) . . . . ?
O3 C9 C10 C11 179.79(17) . . . . ?
O4 C15 C16 C17 -68.8(3) . . . . ?
O4 C15 C16 C18 53.4(4) . . . . ?
N1 C15 C16 C17 110.4(3) . . . . ?
N1 C15 C16 C18 -127.4(2) . . . . ?
C1 S1 C7 C8 103.61(15) . . . . ?
C1 S1 C7 C12 -73.29(16) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C13 -178.0(2) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C7 S1 C1 C2 124.33(17) . . . . ?
C7 S1 C1 C6 -58.21(17) . . . . ?
C7 C8 C9 O3 179.45(16) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C7 C12 N1 175.98(17) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 N1 -176.67(17) . . . . ?
C10 C11 C12 C7 1.6(3) . . . . ?
C12 N1 C15 O4 -2.7(4) . . . . ?
C12 N1 C15 C16 178.1(2) . . . . ?
C12 C7 C8 C9 1.4(3) . . . . ?
C13 C4 C5 C6 176.8(2) . . . . ?
C14 O3 C9 C8 10.1(3) . . . . ?
C14 O3 C9 C10 -170.56(18) . . . . ?
C15 N1 C12 C7 157.9(2) . . . . ?
C15 N1 C12 C11 -23.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
