# 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 
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data_cmrv_kp_1269_autored
_database_code_depnum_ccdc_archive 'CCDC 2401869'
loop_
_audit_author_name
_audit_author_address
'Darshan Mhatre'
;IIT Bombay
India
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_audit_creation_date             2024-11-11
_audit_creation_method           
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
darshansmhatre@chem.iitb.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N2 O4 S2'
_chemical_formula_sum            'C18 H18 N2 O4 S2'
_chemical_formula_weight         390.46
_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                   9.0198(4)
_cell_length_b                   9.8165(4)
_cell_length_c                   11.3146(4)
_cell_angle_alpha                89.792(3)
_cell_angle_beta                 89.757(3)
_cell_angle_gamma                63.581(4)
_cell_volume                     897.19(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3145
_cell_measurement_temperature    150
_cell_measurement_theta_max      36.0890
_cell_measurement_theta_min      2.3710
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2805
_reflns_number_total             3145
_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-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.6066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0966
_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 Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.27006(6) 0.90148(5) 0.49645(4) 0.01947(15) Uani 1 1 d . . . . .
S2 S 0.16651(6) 0.54339(5) 0.40075(4) 0.01982(15) Uani 1 1 d . . . . .
O1 O 0.43522(17) 0.78808(16) 0.51931(13) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.01231(16) 0.67468(16) 0.38471(13) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.14670(17) 0.93409(16) 0.58765(12) 0.0243(3) Uani 1 1 d . . . . .
O4 O 0.18528(18) 0.39974(17) 0.35922(13) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.30973(19) 0.57776(18) 0.33037(14) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.20374(19) 0.84749(18) 0.37871(14) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.151946 0.925577 0.331255 0.024 Uiso 1 1 d R U . . .
C1 C 0.6660(2) 0.4619(2) 0.13122(17) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.7738(3) 0.3088(2) 0.1505(2) 0.0301(5) Uani 1 1 d . . . . .
H2A H 0.758368 0.257314 0.217086 0.036 Uiso 1 1 calc R U . . .
C3 C 0.9037(3) 0.2316(3) 0.0723(2) 0.0435(6) Uani 1 1 d . . . . .
H3 H 0.974001 0.126472 0.084249 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9314(3) 0.3068(3) -0.0227(2) 0.0465(7) Uani 1 1 d . . . . .
H4 H 1.021747 0.254018 -0.074805 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8274(3) 0.4580(3) -0.0412(2) 0.0369(6) Uani 1 1 d . . . . .
H5 H 0.846427 0.510050 -0.106057 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6950(3) 0.5349(3) 0.03413(18) 0.0266(5) Uani 1 1 d . . . . .
H6 H 0.622826 0.638990 0.019550 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5223(2) 0.5403(2) 0.20990(16) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.4375(2) 0.7001(2) 0.23932(16) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.3087(2) 0.7199(2) 0.31297(17) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.4403(2) 0.4701(2) 0.26591(17) 0.0203(4) Uani 1 1 d . . . . .
H10 H 0.468146 0.364846 0.261436 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4774(2) 0.8254(2) 0.20579(16) 0.0196(4) Uani 1 1 d . . . . .
C12 C 0.6326(2) 0.8192(2) 0.22775(17) 0.0228(4) Uani 1 1 d . . . . .
H12 H 0.717887 0.729996 0.261210 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6627(3) 0.9422(3) 0.20105(18) 0.0280(5) Uani 1 1 d . . . . .
H13 H 0.768311 0.937226 0.217005 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5398(3) 1.0729(2) 0.15107(19) 0.0304(5) Uani 1 1 d . . . . .
H14 H 0.561390 1.156789 0.132231 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3861(3) 1.0801(2) 0.12898(19) 0.0309(5) Uani 1 1 d . . . . .
H15 H 0.301387 1.169590 0.095451 0.037 Uiso 1 1 calc R U . . .
C16 C 0.3550(3) 0.9574(2) 0.15550(18) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.249109 0.963086 0.139278 0.031 Uiso 1 1 calc R U . . .
C17 C 0.2733(3) 1.0723(2) 0.45570(19) 0.0286(5) Uani 1 1 d . . . . .
H17A H 0.304782 1.114770 0.523956 0.043 Uiso 1 1 calc R U . . .
H17B H 0.163065 1.144767 0.428522 0.043 Uiso 1 1 calc R U . . .
H17C H 0.353791 1.053095 0.391788 0.043 Uiso 1 1 calc R U . . .
C18 C 0.2273(3) 0.5289(3) 0.54873(18) 0.0263(5) Uani 1 1 d . . . . .
H18A H 0.230457 0.623377 0.572837 0.039 Uiso 1 1 calc R U . . .
H18B H 0.337497 0.443557 0.557845 0.039 Uiso 1 1 calc R U . . .
H18C H 0.147859 0.511775 0.598399 0.039 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 1.4321(14) . ?
S1 O3 1.4426(14) . ?
S1 N2 1.6456(17) . ?
S1 C17 1.750(2) . ?
S2 O2 1.4261(14) . ?
S2 O4 1.4247(15) . ?
S2 N1 1.6714(16) . ?
S2 C18 1.749(2) . ?
N1 C9 1.405(2) . ?
N1 C10 1.388(2) . ?
N2 H2 0.8801 . ?
N2 C9 1.401(2) . ?
C1 C2 1.396(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.474(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.446(3) . ?
C7 C10 1.368(3) . ?
C8 C9 1.369(3) . ?
C8 C11 1.475(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 C16 1.396(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 O3 118.39(9) . . ?
O1 S1 N2 107.40(8) . . ?
O1 S1 C17 109.71(10) . . ?
O3 S1 N2 107.18(8) . . ?
O3 S1 C17 108.22(9) . . ?
N2 S1 C17 105.12(10) . . ?
O2 S2 N1 106.72(8) . . ?
O2 S2 C18 109.90(10) . . ?
O4 S2 O2 119.37(9) . . ?
O4 S2 N1 106.28(8) . . ?
O4 S2 C18 110.10(10) . . ?
N1 S2 C18 103.10(9) . . ?
C9 N1 S2 126.94(13) . . ?
C10 N1 S2 124.35(14) . . ?
C10 N1 C9 108.25(16) . . ?
S1 N2 H2 110.0 . . ?
C9 N2 S1 121.43(13) . . ?
C9 N2 H2 109.9 . . ?
C2 C1 C7 119.88(19) . . ?
C6 C1 C2 118.31(19) . . ?
C6 C1 C7 121.76(18) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C1 128.61(18) . . ?
C10 C7 C1 124.09(18) . . ?
C10 C7 C8 107.26(16) . . ?
C7 C8 C11 129.69(17) . . ?
C9 C8 C7 107.49(17) . . ?
C9 C8 C11 122.75(17) . . ?
N2 C9 N1 121.24(16) . . ?
C8 C9 N1 108.14(16) . . ?
C8 C9 N2 129.94(18) . . ?
N1 C10 H10 125.6 . . ?
C7 C10 N1 108.86(17) . . ?
C7 C10 H10 125.6 . . ?
C12 C11 C8 121.92(17) . . ?
C16 C11 C8 119.43(17) . . ?
C16 C11 C12 118.59(19) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.34(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
S2 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 N2 C9 N1 97.56(19) . . . . ?
S1 N2 C9 C8 -71.8(2) . . . . ?
S2 N1 C9 N2 15.8(3) . . . . ?
S2 N1 C9 C8 -172.80(14) . . . . ?
S2 N1 C10 C7 173.46(13) . . . . ?
O1 S1 N2 C9 -6.21(18) . . . . ?
O2 S2 N1 C9 30.30(18) . . . . ?
O2 S2 N1 C10 -141.01(16) . . . . ?
O3 S1 N2 C9 -134.42(15) . . . . ?
O4 S2 N1 C9 158.70(16) . . . . ?
O4 S2 N1 C10 -12.61(18) . . . . ?
C1 C2 C3 C4 2.4(4) . . . . ?
C1 C7 C8 C9 178.28(18) . . . . ?
C1 C7 C8 C11 -4.6(3) . . . . ?
C1 C7 C10 N1 -178.63(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C7 C8 152.2(2) . . . . ?
C2 C1 C7 C10 -30.5(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C6 C1 C7 C8 -30.2(3) . . . . ?
C6 C1 C7 C10 147.1(2) . . . . ?
C7 C1 C2 C3 176.0(2) . . . . ?
C7 C1 C6 C5 -177.74(19) . . . . ?
C7 C8 C9 N1 -0.2(2) . . . . ?
C7 C8 C9 N2 170.27(19) . . . . ?
C7 C8 C11 C12 -54.5(3) . . . . ?
C7 C8 C11 C16 128.4(2) . . . . ?
C8 C7 C10 N1 -0.9(2) . . . . ?
C8 C11 C12 C13 -176.43(18) . . . . ?
C8 C11 C16 C15 176.52(19) . . . . ?
C9 N1 C10 C7 0.8(2) . . . . ?
C9 C8 C11 C12 122.2(2) . . . . ?
C9 C8 C11 C16 -54.8(3) . . . . ?
C10 N1 C9 N2 -171.79(17) . . . . ?
C10 N1 C9 C8 -0.4(2) . . . . ?
C10 C7 C8 C9 0.6(2) . . . . ?
C10 C7 C8 C11 177.76(18) . . . . ?
C11 C8 C9 N1 -177.54(16) . . . . ?
C11 C8 C9 N2 -7.1(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C17 S1 N2 C9 110.58(16) . . . . ?
C18 S2 N1 C9 -85.48(18) . . . . ?
C18 S2 N1 C10 103.22(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
