# Electronic Supplementary Material (ESI) 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. 
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data_23apra_0m
_database_code_depnum_ccdc_archive 'CCDC 2178470'
loop_
_audit_author_name
_audit_author_address
'RAMESH METRE'
;IIT Jodhpur
India
;
_audit_update_record             
;
2022-06-11 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_audit_creation_date             2022-06-05
_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         'C30 H25 N O4 S'
_chemical_formula_sum            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_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 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1168(14)
_cell_length_b                   17.929(3)
_cell_length_c                   16.686(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.685(6)
_cell_angle_gamma                90
_cell_volume                     2420.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9132
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9338.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35876
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_min         2.762
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5223
_reflns_number_total             5987
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.188
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1522
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.14384(4) 0.22481(2) 0.11080(2) 0.01250(12) Uani 1 1 d . . . . .
O1 O 0.23998(12) 0.15814(6) 0.12481(7) 0.0177(2) Uani 1 1 d . . . . .
O2 O 0.21795(12) 0.29028(6) 0.07986(6) 0.0169(2) Uani 1 1 d . . . . .
O3 O -0.16788(15) 0.22816(6) -0.11878(7) 0.0219(3) Uani 1 1 d . . . . .
O4 O -0.37642(15) 0.38624(6) 0.02171(7) 0.0227(3) Uani 1 1 d . . . . .
N1 N -0.01126(14) 0.20301(7) 0.04392(7) 0.0124(3) Uani 1 1 d . . . . .
C1 C -0.10907(17) 0.13808(8) 0.05648(8) 0.0125(3) Uani 1 1 d . . . . .
C2 C -0.05416(18) 0.06587(8) 0.07140(10) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.058015 0.054531 0.075254 0.022 Uiso 1 1 calc R . . . .
C3 C -0.1717(2) 0.01096(9) 0.08042(10) 0.0203(3) Uani 1 1 d . . . . .
H3 H -0.137741 -0.037879 0.090794 0.024 Uiso 1 1 calc R . . . .
C4 C -0.33965(19) 0.02776(8) 0.07418(9) 0.0173(3) Uani 1 1 d . . . . .
H4 H -0.416458 -0.009848 0.080445 0.021 Uiso 1 1 calc R . . . .
C5 C -0.39352(17) 0.10037(8) 0.05866(9) 0.0146(3) Uani 1 1 d . . . . .
H5 H -0.505755 0.111601 0.054324 0.017 Uiso 1 1 calc R . . . .
C6 C -0.27685(17) 0.15590(8) 0.04971(8) 0.0123(3) Uani 1 1 d . . . . .
C7 C -0.30281(17) 0.23780(8) 0.03321(9) 0.0117(3) Uani 1 1 d . . . . .
H7 H -0.377431 0.244274 -0.015498 0.014 Uiso 1 1 calc R . . . .
C8 C -0.12676(17) 0.26535(8) 0.01729(9) 0.0116(3) Uani 1 1 d . . . . .
H8 H -0.098506 0.311270 0.047182 0.014 Uiso 1 1 calc R . . . .
C9 C -0.11022(18) 0.27596(8) -0.07323(9) 0.0140(3) Uani 1 1 d . . . . .
C10 C -0.02244(17) 0.34175(8) -0.10405(9) 0.0140(3) Uani 1 1 d . . . . .
C11 C 0.05403(19) 0.39695(9) -0.05493(10) 0.0191(3) Uani 1 1 d . . . . .
H11 H 0.049718 0.394338 0.000527 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1366(2) 0.45579(9) -0.08848(11) 0.0253(4) Uani 1 1 d . . . . .
H12 H 0.188045 0.492120 -0.055451 0.030 Uiso 1 1 calc R . . . .
C13 C 0.1420(2) 0.46020(10) -0.17102(11) 0.0271(4) Uani 1 1 d . . . . .
H13 H 0.197957 0.499348 -0.193333 0.032 Uiso 1 1 calc R . . . .
C14 C 0.0642(2) 0.40631(10) -0.22078(10) 0.0251(4) Uani 1 1 d . . . . .
H14 H 0.066875 0.409816 -0.276266 0.030 Uiso 1 1 calc R . . . .
C15 C -0.01728(19) 0.34752(9) -0.18765(9) 0.0192(3) Uani 1 1 d . . . . .
H15 H -0.069017 0.311536 -0.221053 0.023 Uiso 1 1 calc R . . . .
C16 C -0.37429(17) 0.27762(7) 0.10378(9) 0.0127(3) Uani 1 1 d . . . . .
H16A H -0.473917 0.252088 0.116968 0.015 Uiso 1 1 calc R . . . .
H16B H -0.295046 0.275286 0.150487 0.015 Uiso 1 1 calc R . . . .
C17 C -0.41492(17) 0.35894(8) 0.08439(9) 0.0148(3) Uani 1 1 d . . . . .
C18 C -0.50288(17) 0.40340(8) 0.14310(9) 0.0147(3) Uani 1 1 d . . . . .
C19 C -0.56798(19) 0.47260(9) 0.11821(10) 0.0196(3) Uani 1 1 d . . . . .
H19 H -0.552841 0.490220 0.066910 0.024 Uiso 1 1 calc R . . . .
C20 C -0.6552(2) 0.51503(9) 0.17005(11) 0.0226(3) Uani 1 1 d . . . . .
H20 H -0.698799 0.560923 0.153222 0.027 Uiso 1 1 calc R . . . .
C21 C -0.6777(2) 0.48931(9) 0.24684(10) 0.0216(3) Uani 1 1 d . . . . .
H21 H -0.736226 0.517996 0.281278 0.026 Uiso 1 1 calc R . . . .
C22 C -0.61287(19) 0.42070(9) 0.27238(10) 0.0193(3) Uani 1 1 d . . . . .
H22 H -0.627521 0.403547 0.323921 0.023 Uiso 1 1 calc R . . . .
C23 C -0.52597(17) 0.37780(8) 0.22049(9) 0.0158(3) Uani 1 1 d . . . . .
H23 H -0.483022 0.331827 0.237444 0.019 Uiso 1 1 calc R . . . .
C24 C 0.05366(16) 0.24888(8) 0.19924(8) 0.0122(3) Uani 1 1 d . . . . .
C25 C 0.02809(17) 0.32379(8) 0.21661(9) 0.0147(3) Uani 1 1 d . . . . .
H25 H 0.066272 0.361114 0.184140 0.018 Uiso 1 1 calc R . . . .
C26 C -0.05571(18) 0.34163(8) 0.28353(9) 0.0158(3) Uani 1 1 d . . . . .
H26 H -0.074053 0.391462 0.295477 0.019 Uiso 1 1 calc R . . . .
C27 C -0.11274(18) 0.28624(8) 0.33304(9) 0.0145(3) Uani 1 1 d . . . . .
C28 C -0.08206(18) 0.21178(8) 0.31499(9) 0.0163(3) Uani 1 1 d . . . . .
H28 H -0.116954 0.174386 0.348331 0.020 Uiso 1 1 calc R . . . .
C29 C -0.00022(17) 0.19264(9) 0.24801(9) 0.0163(3) Uani 1 1 d . . . . .
H29 H 0.018246 0.142834 0.235994 0.020 Uiso 1 1 calc R . . . .
C30 C -0.20800(19) 0.30592(9) 0.40360(9) 0.0185(3) Uani 1 1 d . . . . .
H30A H -0.161296 0.349851 0.429319 0.028 Uiso 1 1 calc GR . . . .
H30B H -0.202177 0.265312 0.441219 0.028 Uiso 1 1 calc GR . . . .
H30C H -0.321385 0.315180 0.385339 0.028 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 O1 1.4361(11) . ?
S1 O2 1.4342(11) . ?
S1 N1 1.6593(12) . ?
S1 C24 1.7539(14) . ?
O3 C9 1.2136(18) . ?
O4 C17 1.2185(19) . ?
N1 C1 1.4340(18) . ?
N1 C8 1.5026(17) . ?
C1 C2 1.385(2) . ?
C1 C6 1.3944(19) . ?
C2 C3 1.388(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.5055(19) . ?
C7 C8 1.5551(19) . ?
C7 C16 1.5313(19) . ?
C8 C9 1.539(2) . ?
C9 C10 1.491(2) . ?
C10 C11 1.398(2) . ?
C10 C15 1.403(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.384(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.383(2) . ?
C16 C17 1.5237(19) . ?
C17 C18 1.490(2) . ?
C18 C19 1.398(2) . ?
C18 C23 1.397(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.388(2) . ?
C21 C22 1.391(2) . ?
C22 C23 1.392(2) . ?
C24 C25 1.393(2) . ?
C24 C29 1.389(2) . ?
C25 C26 1.391(2) . ?
C26 C27 1.395(2) . ?
C27 C28 1.395(2) . ?
C27 C30 1.5023(19) . ?
C28 C29 1.389(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
O1 S1 N1 106.60(6) . . ?
O1 S1 C24 109.05(7) . . ?
O2 S1 O1 120.10(6) . . ?
O2 S1 N1 105.56(6) . . ?
O2 S1 C24 108.51(7) . . ?
N1 S1 C24 106.14(6) . . ?
C1 N1 S1 119.45(9) . . ?
C1 N1 C8 107.91(10) . . ?
C8 N1 S1 116.38(9) . . ?
C2 C1 N1 127.67(13) . . ?
C2 C1 C6 121.77(13) . . ?
C6 C1 N1 110.54(12) . . ?
C1 C2 C3 117.94(14) . . ?
C2 C3 C4 121.09(14) . . ?
C5 C4 C3 120.51(14) . . ?
C6 C5 C4 118.92(13) . . ?
C1 C6 C7 111.07(12) . . ?
C5 C6 C1 119.77(13) . . ?
C5 C6 C7 129.17(13) . . ?
C6 C7 C8 102.96(11) . . ?
C6 C7 C16 111.73(12) . . ?
C16 C7 C8 113.23(11) . . ?
N1 C8 C7 105.84(11) . . ?
N1 C8 C9 106.25(11) . . ?
C9 C8 C7 111.21(12) . . ?
O3 C9 C8 117.86(13) . . ?
O3 C9 C10 120.88(14) . . ?
C10 C9 C8 121.25(12) . . ?
C11 C10 C9 124.03(14) . . ?
C11 C10 C15 118.89(14) . . ?
C15 C10 C9 117.08(13) . . ?
C12 C11 C10 120.41(15) . . ?
C13 C12 C11 119.95(16) . . ?
C12 C13 C14 120.28(15) . . ?
C15 C14 C13 119.95(16) . . ?
C14 C15 C10 120.51(15) . . ?
C17 C16 C7 111.83(12) . . ?
O4 C17 C16 120.03(13) . . ?
O4 C17 C18 121.32(13) . . ?
C18 C17 C16 118.65(13) . . ?
C19 C18 C17 117.99(14) . . ?
C23 C18 C17 122.66(13) . . ?
C23 C18 C19 119.33(14) . . ?
C20 C19 C18 120.04(15) . . ?
C21 C20 C19 120.36(15) . . ?
C20 C21 C22 120.11(15) . . ?
C21 C22 C23 119.74(15) . . ?
C22 C23 C18 120.42(14) . . ?
C25 C24 S1 119.47(11) . . ?
C29 C24 S1 119.17(12) . . ?
C29 C24 C25 121.24(13) . . ?
C26 C25 C24 118.66(13) . . ?
C25 C26 C27 121.28(14) . . ?
C26 C27 C28 118.66(13) . . ?
C26 C27 C30 120.92(14) . . ?
C28 C27 C30 120.41(14) . . ?
C29 C28 C27 121.03(14) . . ?
C24 C29 C28 119.10(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
