# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_A_a
_audit_block_doi                 10.5517/ccdc.csd.cc2ks4h0
_database_code_depnum_ccdc_archive 'CCDC 2376692'
loop_
_audit_author_name
_audit_author_address
'Cheng siliu'
; Inner Mongolia University of Technology
China
;
_audit_update_record             
;
2024-08-09 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'H S, C14 H16 N'
_chemical_formula_sum            'C14 H17 N S'
_chemical_formula_weight         231.36
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33536 0.55132 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   10.3127(4)
_cell_length_b                   24.2441(10)
_cell_length_c                   5.0951(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1273.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      74.51
_cell_measurement_theta_min      7.31
_exptl_absorpt_coefficient_mu    2.014
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1435 before and 0.0798 after correction. The Ratio of minimum to maximum transmission is 0.5882. The λ/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.2063
_exptl_crystal_description       prism
_exptl_crystal_F_000             498.4846
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12563
_diffrn_reflns_theta_full        74.6485
_diffrn_reflns_theta_max         74.65
_diffrn_reflns_theta_min         7.31
_diffrn_ambient_temperature      273.0
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              6
_reflns_limit_l_min              0
_reflns_number_gt                1046
_reflns_number_total             1338
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3633
_refine_diff_density_min         -0.3494
_refine_diff_density_rms         0.0502
_refine_ls_d_res_high            0.7994
_refine_ls_d_res_low             6.0610
_refine_ls_goodness_of_fit_ref   1.0033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1338
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.0021
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1005P)²+0.2789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1636
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 S1-H1
 1.35 with sigma of 0.01
 H1a-H1
 2.4 with sigma of 0.01
 S1-H1a
 2.7 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b), C7(H7a,H7b)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C2(H2), C1(H1c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.55119(7) 0.75 0.72734(15) 0.0584(3) Uani 1.000000 2 DS T P
N1 N 0.2946(2) 0.75 0.3937(5) 0.0499(6) Uani 1.000000 2 S T P
H1a H 0.3506(2) 0.75 0.5291(5) 0.0599(7) Uiso 1.000000 2 DRS T P
H1b H 0.2137(2) 0.75 0.4600(5) 0.0599(7) Uiso 1.000000 2 RS T P
C3 C 0.1792(4) 0.55326(13) 0.6169(7) 0.0932(10) Uani 1.000000 1 . . .
H3 H 0.1495(4) 0.52130(13) 0.6980(7) 0.1118(12) Uiso 1.000000 1 R . .
C4 C 0.2894(3) 0.57831(13) 0.7051(6) 0.0823(9) Uani 1.000000 1 . . .
H4 H 0.3341(3) 0.56363(13) 0.8475(6) 0.0988(10) Uiso 1.000000 1 R . .
C5 C 0.3349(2) 0.62572(11) 0.5827(5) 0.0642(6) Uani 1.000000 1 . . .
H5 H 0.4108(2) 0.64237(11) 0.6415(5) 0.0771(8) Uiso 1.000000 1 R . .
C6 C 0.2682(2) 0.64804(9) 0.3752(4) 0.0534(5) Uani 1.000000 1 . . .
C7 C 0.3141(2) 0.69903(10) 0.2354(4) 0.0587(6) Uani 1.000000 1 . . .
H7a H 0.2675(2) 0.70261(10) 0.0709(4) 0.0705(7) Uiso 1.000000 1 R . .
H7b H 0.4055(2) 0.69515(10) 0.1949(4) 0.0705(7) Uiso 1.000000 1 R . .
C2 C 0.1130(3) 0.57486(14) 0.4110(7) 0.0933(10) Uani 1.000000 1 . . .
H2 H 0.0377(3) 0.55774(14) 0.3520(7) 0.1120(12) Uiso 1.000000 1 R . .
C1 C 0.1567(3) 0.62209(12) 0.2892(5) 0.0732(7) Uani 1.000000 1 . . .
H1c H 0.1109(3) 0.63660(12) 0.1480(5) 0.0879(9) Uiso 1.000000 1 R . .
H1 H 0.5816(10) 0.75 0.471(2) 1.0(2) Uiso 1.000000 2 DS T P


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 H1 1.346(10) . ?
N1 H1a 0.9000 . ?
N1 H1b 0.9000 . ?
N1 C7 1.489(3) 7_575 ?
N1 C7 1.489(3) . ?
H1a H1 2.400(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(4) . ?
C3 C2 1.357(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C6 C7 1.503(3) . ?
C6 C1 1.382(3) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C2 H2 0.9300 . ?
C2 C1 1.379(4) . ?
C1 H1c 0.9300 . ?

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
H1b N1 H1a 107.9 . . ?
C7 N1 H1a 109.17(13) . . ?
C7 N1 H1a 109.17(13) 7_575 . ?
C7 N1 H1b 109.17(13) . . ?
C7 N1 H1b 109.17(13) 7_575 . ?
C7 N1 C7 112.2(2) . 7_575 ?
H1 H1a N1 122.8(3) . . ?
C4 C3 H3 119.9(2) . . ?
C2 C3 H3 119.93(19) . . ?
C2 C3 C4 120.1(3) . . ?
H4 C4 C3 119.9(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.94(17) . . ?
H5 C5 C4 119.92(17) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.92(15) . . ?
C7 C6 C5 122.1(2) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 119.1(2) . . ?
C6 C7 N1 112.57(18) . 7_575 ?
H7a C7 N1 109.08(13) . 7_575 ?
H7a C7 C6 109.08(13) . . ?
H7b C7 N1 109.08(13) . 7_575 ?
H7b C7 C6 109.08(13) . . ?
H7b C7 H7a 107.8 . . ?
H2 C2 C3 119.87(19) . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.87(19) . . ?
C2 C1 C6 120.5(3) . . ?
H1c C1 C6 119.74(16) . . ?
H1c C1 C2 119.74(19) . . ?
H1a H1 S1 69.4(4) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
S1 H1a 1 2.7000 0.0100 0.3984
S1 H1 1 1.3500 0.0100 0.0043
H1a H1 1 2.4000 0.0100 -0.0003

_chemical_melting_point          '213-215 oC'
