# 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_nts-y2cl
_database_code_depnum_ccdc_archive 'CCDC 2457160'
loop_
_audit_author_name
_audit_author_address
'Yuming Li'
;Tianjin University of Science and Technology
China
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-07-25 downloaded from the CCDC.
;
_audit_creation_date             2025-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        organic
_chemical_formula_moiety         'C24 H21 Cl N2 O2 S'
_chemical_formula_sum            'C24 H22 Cl N2 O2 S'
_chemical_formula_weight         437.94
_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'
Cl Cl 0.1484 0.1585 '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                   7.158(5)
_cell_length_b                   8.464(7)
_cell_length_c                   19.143(15)
_cell_angle_alpha                81.94(2)
_cell_angle_beta                 79.89(2)
_cell_angle_gamma                88.02(2)
_cell_volume                     1130.4(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.978
_cell_measurement_theta_min      2.182
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1208 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.6828. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_preparation       organic
_exptl_crystal_recrystallization_method organic
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8696
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.182
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          organic
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2763
_reflns_number_total             5032
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0868
_refine_ls_restrained_S_all      1.031
_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)+(0.0679P)²+1.9980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2269
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C23(H23), C20(H20), C14(H14), C6(H6), C13(H13), C4(H4),
 C21(H21), C22(H22), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_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 0.47683(17) 0.50262(15) 0.22657(7) 0.0427(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2871(2) 0.16424(19) 0.45920(9) 0.0699(5) Uani 1 1 d . . . . .
O2 O 0.5129(5) 0.5198(5) 0.2967(2) 0.0592(10) Uani 1 1 d . . . . .
O1 O 0.3706(5) 0.6297(4) 0.1936(2) 0.0642(11) Uani 1 1 d . . . . .
N2 N 0.2106(5) 0.1146(4) 0.2372(2) 0.0402(9) Uani 1 1 d . . . . .
N1 N 0.3986(5) 0.3318(5) 0.2228(2) 0.0419(10) Uani 1 1 d . . . . .
C8 C 0.2392(6) 0.2626(5) 0.2524(2) 0.0378(10) Uani 1 1 d . . . . .
C9 C 0.0664(6) 0.3091(5) 0.3010(2) 0.0343(10) Uani 1 1 d . . . . .
C10 C -0.0658(6) 0.1721(5) 0.3083(2) 0.0369(10) Uani 1 1 d . . . . .
C17 C 0.0870(6) 0.4009(5) 0.3638(2) 0.0381(11) Uani 1 1 d . . . . .
H17 H 0.2186 0.4380 0.3629 0.046 Uiso 1 1 calc R . . . .
C11 C 0.0292(6) 0.0586(5) 0.2692(3) 0.0391(11) Uani 1 1 d . . . . .
C16 C -0.0036(7) 0.4786(5) 0.3038(3) 0.0408(11) Uani 1 1 d . . . . .
H16A H 0.0681 0.5636 0.2698 0.049 Uiso 1 1 calc R . . . .
H16B H -0.1425 0.4968 0.3135 0.049 Uiso 1 1 calc R . . . .
C18 C -0.0202(6) 0.3489(5) 0.4365(2) 0.0376(10) Uani 1 1 d . . . . .
C12 C -0.0543(8) -0.0823(6) 0.2622(3) 0.0495(13) Uani 1 1 d . . . . .
H12 H 0.0117 -0.1584 0.2347 0.059 Uiso 1 1 calc R . . . .
C5 C 0.7006(7) 0.4944(6) 0.1704(3) 0.0424(11) Uani 1 1 d . . . . .
C15 C -0.2484(7) 0.1474(6) 0.3418(3) 0.0437(12) Uani 1 1 d . . . . .
H15 H -0.3151 0.2252 0.3681 0.052 Uiso 1 1 calc R . . . .
C19 C 0.0602(7) 0.2402(6) 0.4849(3) 0.0436(12) Uani 1 1 d . . . . .
C23 C -0.1991(7) 0.4099(7) 0.4609(3) 0.0523(13) Uani 1 1 d . . . . .
H23 H -0.2589 0.4846 0.4299 0.063 Uiso 1 1 calc R . . . .
C20 C -0.0313(8) 0.1924(7) 0.5538(3) 0.0547(14) Uani 1 1 d . . . . .
H20 H 0.0271 0.1171 0.5851 0.066 Uiso 1 1 calc R . . . .
C14 C -0.3352(7) 0.0063(6) 0.3366(3) 0.0540(14) Uani 1 1 d . . . . .
H14 H -0.4621 -0.0130 0.3604 0.065 Uiso 1 1 calc R . . . .
C6 C 0.7892(7) 0.3527(7) 0.1567(3) 0.0539(14) Uani 1 1 d . . . . .
H6 H 0.7272 0.2545 0.1754 0.065 Uiso 1 1 calc R . . . .
C13 C -0.2402(8) -0.1060(6) 0.2977(3) 0.0549(14) Uani 1 1 d . . . . .
H13 H -0.3029 -0.2016 0.2951 0.066 Uiso 1 1 calc R . . . .
C4 C 0.7928(8) 0.6368(7) 0.1439(3) 0.0561(14) Uani 1 1 d . . . . .
H4 H 0.7328 0.7353 0.1533 0.067 Uiso 1 1 calc R . . . .
C24 C 0.3476(8) 0.0274(6) 0.1917(3) 0.0610(16) Uani 1 1 d . . . . .
H24A H 0.3071 0.0284 0.1454 0.091 Uiso 1 1 calc GR . . . .
H24B H 0.3564 -0.0831 0.2146 0.091 Uiso 1 1 calc GR . . . .
H24C H 0.4720 0.0778 0.1845 0.091 Uiso 1 1 calc GR . . . .
C21 C -0.2061(8) 0.2539(7) 0.5766(3) 0.0575(15) Uani 1 1 d . . . . .
H21 H -0.2698 0.2224 0.6242 0.069 Uiso 1 1 calc R . . . .
C22 C -0.2903(7) 0.3619(7) 0.5305(3) 0.0593(15) Uani 1 1 d . . . . .
H22 H -0.4125 0.4041 0.5466 0.071 Uiso 1 1 calc R . . . .
C2 C 1.0634(8) 0.4964(9) 0.0893(3) 0.0615(16) Uani 1 1 d . . . . .
C7 C 0.9692(8) 0.3529(8) 0.1157(3) 0.0626(16) Uani 1 1 d . . . . .
H7 H 1.0289 0.2548 0.1056 0.075 Uiso 1 1 calc R . . . .
C3 C 0.9711(8) 0.6346(8) 0.1043(3) 0.0685(17) Uani 1 1 d . . . . .
H3 H 1.0331 0.7331 0.0864 0.082 Uiso 1 1 calc R . . . .
C1 C 1.2606(9) 0.4947(10) 0.0444(4) 0.090(2) Uani 1 1 d . . . . .
H1A H 1.3558 0.5018 0.0749 0.135 Uiso 1 1 calc GR . . . .
H1B H 1.2734 0.5859 0.0063 0.135 Uiso 1 1 calc GR . . . .
H1C H 1.2799 0.3953 0.0232 0.135 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 O2 1.438(4) . ?
S1 O1 1.433(4) . ?
S1 N1 1.584(4) . ?
S1 C5 1.771(5) . ?
Cl1 C19 1.741(5) . ?
N2 C8 1.355(6) . ?
N2 C11 1.402(6) . ?
N2 C24 1.448(6) . ?
N1 C8 1.301(6) . ?
C8 C9 1.488(6) . ?
C9 C10 1.498(6) . ?
C9 C17 1.549(6) . ?
C9 C16 1.509(6) . ?
C10 C11 1.386(6) . ?
C10 C15 1.361(6) . ?
C17 C16 1.481(6) . ?
C17 C18 1.482(6) . ?
C11 C12 1.386(7) . ?
C18 C19 1.396(7) . ?
C18 C23 1.391(6) . ?
C12 C13 1.391(7) . ?
C5 C6 1.373(7) . ?
C5 C4 1.383(7) . ?
C15 C14 1.388(7) . ?
C19 C20 1.378(7) . ?
C23 C22 1.388(7) . ?
C20 C21 1.362(8) . ?
C14 C13 1.377(8) . ?
C6 C7 1.386(7) . ?
C4 C3 1.366(8) . ?
C21 C22 1.379(8) . ?
C2 C7 1.396(8) . ?
C2 C3 1.364(9) . ?
C2 C1 1.519(8) . ?

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
O2 S1 N1 112.6(2) . . ?
O2 S1 C5 106.9(2) . . ?
O1 S1 O2 115.9(3) . . ?
O1 S1 N1 112.7(2) . . ?
O1 S1 C5 107.0(2) . . ?
N1 S1 C5 100.1(2) . . ?
C8 N2 C11 111.5(4) . . ?
C8 N2 C24 124.3(4) . . ?
C11 N2 C24 124.2(4) . . ?
C8 N1 S1 131.4(4) . . ?
N2 C8 C9 107.6(4) . . ?
N1 C8 N2 117.6(4) . . ?
N1 C8 C9 134.8(4) . . ?
C8 C9 C10 104.3(4) . . ?
C8 C9 C17 119.6(4) . . ?
C8 C9 C16 124.2(4) . . ?
C10 C9 C17 123.5(4) . . ?
C10 C9 C16 122.4(4) . . ?
C16 C9 C17 57.9(3) . . ?
C11 C10 C9 107.2(4) . . ?
C15 C10 C9 132.6(4) . . ?
C15 C10 C11 120.1(4) . . ?
C16 C17 C9 59.7(3) . . ?
C16 C17 C18 123.2(4) . . ?
C18 C17 C9 120.0(4) . . ?
C10 C11 N2 109.3(4) . . ?
C12 C11 N2 128.0(4) . . ?
C12 C11 C10 122.6(4) . . ?
C17 C16 C9 62.4(3) . . ?
C19 C18 C17 120.4(4) . . ?
C23 C18 C17 122.5(4) . . ?
C23 C18 C19 117.0(5) . . ?
C11 C12 C13 116.3(5) . . ?
C6 C5 S1 122.4(4) . . ?
C6 C5 C4 119.7(5) . . ?
C4 C5 S1 117.7(4) . . ?
C10 C15 C14 118.6(5) . . ?
C18 C19 Cl1 119.7(4) . . ?
C20 C19 Cl1 117.8(4) . . ?
C20 C19 C18 122.5(5) . . ?
C22 C23 C18 120.2(5) . . ?
C21 C20 C19 119.5(5) . . ?
C13 C14 C15 121.0(5) . . ?
C5 C6 C7 120.0(5) . . ?
C14 C13 C12 121.3(5) . . ?
C3 C4 C5 119.4(6) . . ?
C20 C21 C22 119.8(5) . . ?
C21 C22 C23 121.0(5) . . ?
C7 C2 C1 119.9(6) . . ?
C3 C2 C7 117.7(5) . . ?
C3 C2 C1 122.4(6) . . ?
C6 C7 C2 120.5(6) . . ?
C2 C3 C4 122.6(6) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.036 0.000 0.000 139 45 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
