# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_159
_database_code_depnum_ccdc_archive 'CCDC 2270405'
loop_
_audit_author_name
_audit_author_address
'Dr. V. Ram Kumar'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-06-16 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 S'
_chemical_formula_sum            'C20 H20 N2 S'
_chemical_formula_weight         320.44

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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. 
;

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                   5.7116(3)
_cell_length_b                   9.0628(5)
_cell_length_c                   34.5624(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.604(3)
_cell_angle_gamma                90
_cell_volume                     1787.21(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4085
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      20.65

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23357
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.180
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3154
_reflns_number_gt                2113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.6137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5937(5) 0.1942(3) 0.19003(7) 0.0771(8) Uani 1 1 d . . . . .
H1 H 0.6421 0.1515 0.1673 0.093 Uiso 1 1 calc R U . . .
C2 C 0.4167(6) 0.1293(3) 0.20912(8) 0.0975(10) Uani 1 1 d . . . . .
H2 H 0.3465 0.0438 0.1993 0.117 Uiso 1 1 calc R U . . .
C3 C 0.3435(5) 0.1894(4) 0.24223(9) 0.0868(8) Uani 1 1 d . . . . .
H3 H 0.2206 0.1463 0.2549 0.104 Uiso 1 1 calc R U . . .
C4 C 0.4488(6) 0.3121(3) 0.25695(8) 0.0905(9) Uani 1 1 d . . . . .
H4 H 0.4002 0.3521 0.2800 0.109 Uiso 1 1 calc R U . . .
C5 C 0.6307(5) 0.3794(3) 0.23753(7) 0.0767(8) Uani 1 1 d . . . . .
H5 H 0.7027 0.4637 0.2477 0.092 Uiso 1 1 calc R U . . .
C6 C 0.7025(4) 0.3204(2) 0.20341(6) 0.0524(5) Uani 1 1 d . . . . .
C7 C 0.8916(4) 0.3919(2) 0.18105(6) 0.0554(6) Uani 1 1 d . . . . .
H7A H 0.9846 0.3151 0.1696 0.066 Uiso 1 1 calc R U . . .
H7B H 0.9941 0.4467 0.1990 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8011(3) 0.4979(2) 0.14841(6) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.6487(4) 0.4175(2) 0.12007(6) 0.0515(5) Uani 1 1 d . . . . .
C10 C 0.6583(4) 0.6170(2) 0.16475(6) 0.0531(5) Uani 1 1 d . . . . .
C11 C 1.0070(3) 0.5646(2) 0.12698(6) 0.0533(5) Uani 1 1 d . . . . .
H11A H 1.1125 0.6133 0.1457 0.064 Uiso 1 1 calc R U . . .
H11B H 1.0931 0.4854 0.1152 0.064 Uiso 1 1 calc R U . . .
C12 C 0.9312(4) 0.6754(3) 0.09560(7) 0.0650(6) Uani 1 1 d . . . . .
H12A H 0.8047 0.6329 0.0796 0.078 Uiso 1 1 calc R U . . .
H12B H 0.8713 0.7632 0.1078 0.078 Uiso 1 1 calc R U . . .
C13 C 1.1273(4) 0.7190(2) 0.07017(6) 0.0515(5) Uani 1 1 d . . . . .
C14 C 1.2670(3) 0.8425(2) 0.07717(6) 0.0496(5) Uani 1 1 d . . . . .
C15 C 1.4414(4) 0.8738(3) 0.05166(8) 0.0747(7) Uani 1 1 d . . . . .
H15 H 1.5361 0.9562 0.0560 0.090 Uiso 1 1 calc R U . . .
C16 C 1.4767(6) 0.7852(4) 0.02013(9) 0.1013(11) Uani 1 1 d . . . . .
H16 H 1.5933 0.8085 0.0032 0.122 Uiso 1 1 calc R U . . .
C17 C 1.3422(7) 0.6646(4) 0.01376(8) 0.1047(12) Uani 1 1 d . . . . .
H17 H 1.3667 0.6041 -0.0074 0.126 Uiso 1 1 calc R U . . .
C18 C 1.1708(5) 0.6315(3) 0.03839(7) 0.0800(8) Uani 1 1 d . . . . .
H18 H 1.0800 0.5477 0.0338 0.096 Uiso 1 1 calc R U . . .
C19 C 1.2355(4) 0.9444(3) 0.11052(7) 0.0689(7) Uani 1 1 d . . . . .
H19A H 1.3762 1.0036 0.1143 0.083 Uiso 1 1 calc R U . . .
H19B H 1.2198 0.8856 0.1337 0.083 Uiso 1 1 calc R U . . .
C20 C 1.0371(5) 1.1540(3) 0.06046(7) 0.0827(8) Uani 1 1 d . . . . .
H20A H 1.1844 1.2050 0.0623 0.124 Uiso 1 1 calc R U . . .
H20B H 0.9135 1.2232 0.0544 0.124 Uiso 1 1 calc R U . . .
H20C H 1.0406 1.0809 0.0404 0.124 Uiso 1 1 calc R U . . .
N1 N 0.5382(4) 0.3556(2) 0.09738(6) 0.0757(6) Uani 1 1 d . . . . .
N2 N 0.5505(4) 0.7095(2) 0.17705(6) 0.0756(6) Uani 1 1 d . . . . .
S1 S 0.98644(12) 1.06674(7) 0.10534(2) 0.0761(2) Uani 1 1 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
C1 C2 1.365(3) . ?
C1 C6 1.371(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 C8 1.552(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.473(3) . ?
C8 C10 1.480(3) . ?
C8 C11 1.541(3) . ?
C9 N1 1.132(3) . ?
C10 N2 1.134(3) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.386(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.494(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.348(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 S1 1.806(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 S1 1.776(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 C1 C6 122.0(2) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 117.7(2) . . ?
C1 C6 C7 120.7(2) . . ?
C5 C6 C7 121.5(2) . . ?
C6 C7 C8 114.65(16) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C10 107.15(16) . . ?
C9 C8 C11 108.38(17) . . ?
C10 C8 C11 110.05(17) . . ?
C9 C8 C7 110.14(16) . . ?
C10 C8 C7 110.17(17) . . ?
C11 C8 C7 110.86(15) . . ?
N1 C9 C8 177.5(2) . . ?
N2 C10 C8 179.1(3) . . ?
C12 C11 C8 113.69(16) . . ?
C12 C11 H11A 108.8 . . ?
C8 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C8 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.13(18) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 118.5(2) . . ?
C18 C13 C12 118.5(2) . . ?
C14 C13 C12 123.1(2) . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 C19 118.6(2) . . ?
C13 C14 C19 122.95(19) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 122.0(3) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
C14 C19 S1 115.13(15) . . ?
C14 C19 H19A 108.5 . . ?
S1 C19 H19A 108.5 . . ?
C14 C19 H19B 108.5 . . ?
S1 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 S1 C19 101.61(12) . . ?

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
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C1 C6 C7 C8 84.6(3) . . . . ?
C5 C6 C7 C8 -94.6(2) . . . . ?
C6 C7 C8 C9 -59.6(2) . . . . ?
C6 C7 C8 C10 58.4(2) . . . . ?
C6 C7 C8 C11 -179.54(18) . . . . ?
C9 C8 C11 C12 61.6(2) . . . . ?
C10 C8 C11 C12 -55.3(2) . . . . ?
C7 C8 C11 C12 -177.45(18) . . . . ?
C8 C11 C12 C13 -169.60(18) . . . . ?
C11 C12 C13 C18 86.1(3) . . . . ?
C11 C12 C13 C14 -93.7(2) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 C15 -179.3(2) . . . . ?
C18 C13 C14 C19 180.0(2) . . . . ?
C12 C13 C14 C19 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C19 C14 C15 C16 -179.1(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C13 0.4(4) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
C15 C14 C19 S1 104.0(2) . . . . ?
C13 C14 C19 S1 -75.0(2) . . . . ?
C14 C19 S1 C20 -54.6(2) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.032

