# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2159229'
loop_
_audit_author_name
_audit_author_address
'Yunhe Lv'
;Anyang Normal University
China
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O2 S'
_chemical_formula_weight         286.34

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.6746(3)
_cell_length_b                   9.5180(4)
_cell_length_c                   10.4880(5)
_cell_angle_alpha                100.7100(15)
_cell_angle_beta                 90.3641(15)
_cell_angle_gamma                116.6448(14)
_cell_volume                     756.52(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4756
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            14849
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.656
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3065
_reflns_number_gt                2358
_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    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0769P)²+0.0958P] 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         3065
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
S1 S 0.58168(8) 0.99683(7) 0.79708(5) 0.0740(2) Uani 1 1 d . . . . .
C9 C 0.6410(2) 0.9657(2) 0.63671(17) 0.0572(4) Uani 1 1 d . . . . .
C8 C 0.6879(3) 0.9170(3) 0.88688(18) 0.0699(5) Uani 1 1 d . . . . .
H8A H 0.811204 0.970844 0.878514 0.084 Uiso 1 1 calc R U . . .
H8B H 0.672191 0.940815 0.978471 0.084 Uiso 1 1 calc R U . . .
O2 O 0.6570(3) 1.1663(2) 0.84691(16) 0.1076(7) Uani 1 1 d . . . . .
C6 C 0.6231(3) 0.7395(3) 0.84324(18) 0.0670(5) Uani 1 1 d . . . . .
O1 O 0.3981(2) 0.9032(3) 0.79350(16) 0.0949(6) Uani 1 1 d . . . . .
C12 C 0.7356(3) 0.9161(3) 0.39041(18) 0.0622(5) Uani 1 1 d . . . . .
C10 C 0.5344(3) 0.8295(2) 0.54729(18) 0.0650(5) Uani 1 1 d . . . . .
H10A H 0.430805 0.754414 0.569973 0.078 Uiso 1 1 calc R U . . .
C5 C 0.7133(3) 0.6846(3) 0.7706(2) 0.0710(5) Uani 1 1 d . . . . .
C11 C 0.5826(3) 0.8050(3) 0.42313(19) 0.0693(5) Uani 1 1 d . . . . .
H11A H 0.511104 0.713047 0.361614 0.083 Uiso 1 1 calc R U . . .
C4 C 0.8088(3) 0.6282(3) 0.7039(2) 0.0766(6) Uani 1 1 d . . . . .
C15 C 0.7941(3) 1.0793(3) 0.6048(2) 0.0710(5) Uani 1 1 d . . . . .
H15A H 0.864613 1.172145 0.665889 0.085 Uiso 1 1 calc R U . . .
C14 C 0.8407(3) 1.0530(3) 0.4810(2) 0.0757(6) Uani 1 1 d . . . . .
H14A H 0.944066 1.128259 0.458159 0.091 Uiso 1 1 calc R U . . .
C13 C 0.7906(3) 0.8889(3) 0.2634(2) 0.0826(7) Uani 1 1 d . . . . .
N2 N 0.8406(3) 0.8714(4) 0.1648(2) 0.1148(9) Uani 1 1 d . . . . .
C7 C 0.4549(3) 0.6289(4) 0.8865(3) 0.0909(7) Uani 1 1 d . . . . .
H7A H 0.437462 0.520144 0.862109 0.136 Uiso 1 1 calc R U . . .
H7B H 0.361282 0.637866 0.845512 0.136 Uiso 1 1 calc R U . . .
H7C H 0.458164 0.658115 0.979512 0.136 Uiso 1 1 calc R U . . .
C1 C 0.7846(3) 0.5922(3) 0.5637(3) 0.0867(7) Uani 1 1 d . . . . .
N1 N 0.7713(4) 0.5628(3) 0.4531(3) 0.1201(9) Uani 1 1 d . . . . .
C2 C 0.9479(4) 0.5981(4) 0.7638(4) 0.1094(9) Uani 1 1 d . . . . .
H2B H 0.917026 0.484819 0.737334 0.131 Uiso 1 1 calc R U . . .
H2C H 1.056607 0.658145 0.729643 0.131 Uiso 1 1 calc R U . . .
C3 C 0.9732(5) 0.6430(6) 0.9045(4) 0.1448(14) Uani 1 1 d . . . . .
H3A H 1.071410 0.632945 0.935384 0.217 Uiso 1 1 calc R U . . .
H3B H 0.871603 0.573631 0.939653 0.217 Uiso 1 1 calc R U . . .
H3C H 0.993370 0.752403 0.931960 0.217 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 O2 1.4280(19) . ?
S1 O1 1.4302(19) . ?
S1 C9 1.7732(18) . ?
S1 C8 1.787(2) . ?
C9 C10 1.370(3) . ?
C9 C15 1.377(3) . ?
C8 C6 1.496(3) . ?
C6 C5 1.301(3) . ?
C6 C7 1.500(3) . ?
C12 C11 1.371(3) . ?
C12 C14 1.376(3) . ?
C12 C13 1.436(3) . ?
C10 C11 1.381(3) . ?
C5 C4 1.316(3) . ?
C4 C1 1.439(4) . ?
C4 C2 1.517(4) . ?
C15 C14 1.375(3) . ?
C13 N2 1.136(3) . ?
C1 N1 1.134(3) . ?
C2 C3 1.444(5) . ?

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 O1 118.72(12) . . ?
O2 S1 C9 107.65(11) . . ?
O1 S1 C9 108.29(10) . . ?
O2 S1 C8 108.04(12) . . ?
O1 S1 C8 109.17(11) . . ?
C9 S1 C8 103.99(9) . . ?
C10 C9 C15 121.36(17) . . ?
C10 C9 S1 119.55(15) . . ?
C15 C9 S1 119.09(15) . . ?
C6 C8 S1 113.78(14) . . ?
C5 C6 C8 119.8(2) . . ?
C5 C6 C7 121.7(2) . . ?
C8 C6 C7 118.45(19) . . ?
C11 C12 C14 120.03(18) . . ?
C11 C12 C13 120.6(2) . . ?
C14 C12 C13 119.3(2) . . ?
C9 C10 C11 119.24(18) . . ?
C6 C5 C4 176.4(2) . . ?
C12 C11 C10 120.07(18) . . ?
C5 C4 C1 119.5(2) . . ?
C5 C4 C2 124.8(2) . . ?
C1 C4 C2 115.7(2) . . ?
C14 C15 C9 118.74(19) . . ?
C15 C14 C12 120.55(19) . . ?
N2 C13 C12 177.3(3) . . ?
N1 C1 C4 177.2(3) . . ?
C3 C2 C4 113.8(2) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033



