# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_exp_12487
_database_code_depnum_ccdc_archive 'CCDC 2247188'
loop_
_audit_author_name
_audit_author_address
zyk
;Guang xi university
China
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2026-05-14 downloaded from the CCDC.
;
_audit_creation_date             2023-02-02
_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         'C18 H17 N O S'
_chemical_formula_sum            'C18 H17 N O S'
_chemical_formula_weight         295.38
_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                   8.9181(9)
_cell_length_b                   9.3908(10)
_cell_length_c                   10.8301(12)
_cell_angle_alpha                113.868(10)
_cell_angle_beta                 100.187(9)
_cell_angle_gamma                104.576(9)
_cell_volume                     761.90(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.6480
_cell_measurement_theta_min      4.3090
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6169
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.304
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_temperature      273
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  34.00   1.00    1.58    --   15.81  57.00   0.00   26
  2  ω     43.00  72.00   1.00    1.58    --   15.81  57.00   0.00   29
  3  ω    -11.00  83.00   1.00    1.58    --   15.81  77.00-120.00   94
  4  ω    -48.00  43.00   1.00    1.58    --   15.81 -77.00 120.00   91
  5  ω    -51.00  31.00   1.00    1.58    --   15.81 -57.00   0.00   82
  6  ω     -4.00  22.00   1.00    1.58    --  -16.59 -99.00   0.00   26
  7  ω     15.00  41.00   1.00    1.58    --   15.34  57.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0579572000
_diffrn_orient_matrix_UB_12      -0.0735737000
_diffrn_orient_matrix_UB_13      -0.0088061000
_diffrn_orient_matrix_UB_21      -0.0243187000
_diffrn_orient_matrix_UB_22      0.0488808000
_diffrn_orient_matrix_UB_23      0.0566185000
_diffrn_orient_matrix_UB_31      -0.0595523000
_diffrn_orient_matrix_UB_32      0.0054346000
_diffrn_orient_matrix_UB_33      -0.0490967000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2215
_reflns_number_total             3466
_reflns_odcompleteness_completeness 98.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0837
_refine_ls_restrained_S_all      1.001
_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)+(0.1745P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2843
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C1(H1), C3(H3), C11(H11), C12(H12), C2(H2)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.17444(9) 0.21249(10) 0.43282(10) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.2234(3) 0.2372(4) 0.1845(3) 0.0411(8) Uani 1 1 d . . . . .
C7 C 0.2170(3) 0.5278(4) 0.5326(4) 0.0360(8) Uani 1 1 d . . . . .
C6 C 0.1643(3) 0.4783(4) 0.6321(4) 0.0356(8) Uani 1 1 d . . . . .
C9 C 0.2837(4) 0.3886(4) 0.2990(4) 0.0346(8) Uani 1 1 d . . . . .
C8 C 0.2291(3) 0.3984(4) 0.4214(4) 0.0320(7) Uani 1 1 d . . . . .
C5 C 0.1407(4) 0.3100(4) 0.5909(4) 0.0367(8) Uani 1 1 d . . . . .
C15 C 0.2513(4) 0.7015(4) 0.5539(4) 0.0393(9) Uani 1 1 d . . . . .
H15A H 0.170242 0.742382 0.590045 0.047 Uiso 1 1 calc R . . . .
H15B H 0.242255 0.700740 0.463049 0.047 Uiso 1 1 calc R . . . .
C16 C 0.4208(4) 0.8190(4) 0.6574(4) 0.0404(9) Uani 1 1 d . . . . .
H16A H 0.428192 0.819149 0.747936 0.048 Uiso 1 1 calc R . . . .
H16B H 0.500532 0.775118 0.621622 0.048 Uiso 1 1 calc R . . . .
C4 C 0.0914(4) 0.2388(5) 0.6766(5) 0.0493(10) Uani 1 1 d . . . . .
H4 H 0.076404 0.127629 0.650297 0.059 Uiso 1 1 calc R . . . .
O1 O 0.3704(4) 1.0428(4) 0.6337(5) 0.1084(18) Uani 1 1 d . . . . .
C10 C 0.3998(4) 0.5222(5) 0.3035(4) 0.0471(10) Uani 1 1 d . . . . .
H10 H 0.441354 0.626093 0.384064 0.057 Uiso 1 1 calc R . . . .
C17 C 0.4657(4) 0.9951(4) 0.6827(5) 0.0508(11) Uani 1 1 d . . . . .
C13 C 0.2734(5) 0.2160(6) 0.0716(5) 0.0508(10) Uani 1 1 d . . . . .
C1 C 0.1330(4) 0.5718(5) 0.7563(4) 0.0509(10) Uani 1 1 d . . . . .
H1 H 0.144993 0.682483 0.783162 0.061 Uiso 1 1 calc R . . . .
C3 C 0.0664(5) 0.3360(6) 0.7981(4) 0.0558(11) Uani 1 1 d . . . . .
H3 H 0.036089 0.290310 0.855719 0.067 Uiso 1 1 calc R . . . .
C11 C 0.4525(5) 0.4989(6) 0.1875(5) 0.0572(12) Uani 1 1 d . . . . .
H11 H 0.531548 0.586494 0.189248 0.069 Uiso 1 1 calc R . . . .
C12 C 0.3882(5) 0.3471(6) 0.0703(5) 0.0610(12) Uani 1 1 d . . . . .
H12 H 0.420188 0.330474 -0.010070 0.073 Uiso 1 1 calc R . . . .
C2 C 0.0847(5) 0.5022(6) 0.8388(5) 0.0620(12) Uani 1 1 d . . . . .
H2 H 0.064385 0.565209 0.921308 0.074 Uiso 1 1 calc R . . . .
C18 C 0.6379(5) 1.1097(5) 0.7700(6) 0.0802(17) Uani 1 1 d . . . . .
H18A H 0.670387 1.093087 0.851052 0.120 Uiso 1 1 calc GR . . . .
H18B H 0.645040 1.223247 0.801618 0.120 Uiso 1 1 calc GR . . . .
H18C H 0.708741 1.086171 0.713377 0.120 Uiso 1 1 calc GR . . . .
C14 C 0.2037(7) 0.0446(7) -0.0530(6) 0.0840(16) Uani 1 1 d . . . . .
H14A H 0.275699 -0.014638 -0.046778 0.126 Uiso 1 1 calc GR . . . .
H14B H 0.191831 0.052884 -0.139475 0.126 Uiso 1 1 calc GR . . . .
H14C H 0.098890 -0.014233 -0.052762 0.126 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 C8 1.752(3) . ?
S1 C5 1.706(4) . ?
N1 C9 1.342(4) . ?
N1 C13 1.331(5) . ?
C7 C6 1.440(5) . ?
C7 C8 1.367(5) . ?
C7 C15 1.492(5) . ?
C6 C5 1.403(5) . ?
C6 C1 1.400(5) . ?
C9 C8 1.467(5) . ?
C9 C10 1.388(4) . ?
C5 C4 1.414(5) . ?
C15 C16 1.523(4) . ?
C16 C17 1.494(5) . ?
C4 C3 1.360(6) . ?
O1 C17 1.196(5) . ?
C10 C11 1.373(6) . ?
C17 C18 1.497(5) . ?
C13 C12 1.396(6) . ?
C13 C14 1.496(7) . ?
C1 C2 1.370(6) . ?
C3 C2 1.395(7) . ?
C11 C12 1.356(7) . ?

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
C5 S1 C8 91.11(17) . . ?
C13 N1 C9 119.2(3) . . ?
C6 C7 C15 121.8(3) . . ?
C8 C7 C6 111.8(3) . . ?
C8 C7 C15 126.4(3) . . ?
C5 C6 C7 111.8(3) . . ?
C1 C6 C7 129.4(3) . . ?
C1 C6 C5 118.8(4) . . ?
N1 C9 C8 115.5(3) . . ?
N1 C9 C10 121.4(3) . . ?
C10 C9 C8 122.9(3) . . ?
C7 C8 S1 112.7(3) . . ?
C7 C8 C9 132.1(3) . . ?
C9 C8 S1 115.2(3) . . ?
C6 C5 S1 112.6(3) . . ?
C6 C5 C4 120.1(4) . . ?
C4 C5 S1 127.3(3) . . ?
C7 C15 C16 111.9(3) . . ?
C17 C16 C15 115.3(3) . . ?
C3 C4 C5 118.8(4) . . ?
C11 C10 C9 119.1(4) . . ?
C16 C17 C18 116.9(3) . . ?
O1 C17 C16 122.1(3) . . ?
O1 C17 C18 121.0(4) . . ?
N1 C13 C12 121.5(4) . . ?
N1 C13 C14 117.2(4) . . ?
C12 C13 C14 121.3(4) . . ?
C2 C1 C6 120.8(4) . . ?
C4 C3 C2 122.0(4) . . ?
C12 C11 C10 119.4(4) . . ?
C11 C12 C13 119.4(4) . . ?
C1 C2 C3 119.5(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 24.220
_oxdiff_exptl_absorpt_empirical_full_min 0.371
