# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20220501LT_0m
_database_code_depnum_ccdc_archive 'CCDC 2271515'
loop_
_audit_author_name
_audit_author_address
'Seong Jun Park'
;Korea Research Institute of Chemical Technology
South Korea
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            OIS-S-2021-152
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O2 S'
_chemical_formula_weight         258.29

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.3198(2)
_cell_length_b                   9.8246(2)
_cell_length_c                   14.0426(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1147.82(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.5301
_cell_measurement_theta_max      32.8282

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'f and w scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19508
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3293
_reflns_number_gt                3232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.885
_reflns_Friedel_fraction_full    0.991

_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (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)+(0.0513P)²+0.3042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.003(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3293
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.19589(4) 0.45992(4) 0.46240(4) 0.01331(11) Uani 1 1 d . . . . .
O1 O 0.10245(15) 0.58209(14) 0.44580(10) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.26034(18) 0.23961(15) 0.25272(11) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.18074(19) 0.34369(19) 0.38862(12) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.4419(2) 0.37881(17) 0.32308(12) 0.0161(3) Uani 1 1 d . . . . .
H2 H 0.507606 0.365023 0.274942 0.019 Uiso 1 1 calc R U . . .
C1 C 0.2926(2) 0.31809(18) 0.31854(14) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.4973(2) 0.45991(18) 0.39720(14) 0.0140(3) Uani 1 1 d . . . . .
C3 C 0.6575(2) 0.5051(2) 0.39784(15) 0.0181(4) Uani 1 1 d . . . . .
H3 H 0.728059 0.480024 0.347643 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7125(2) 0.58602(19) 0.47128(17) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.820901 0.616342 0.470601 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6120(2) 0.6246(2) 0.54704(15) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.652772 0.678275 0.597863 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4537(2) 0.58372(19) 0.54673(14) 0.0172(3) Uani 1 1 d . . . . .
H6 H 0.383336 0.610555 0.596613 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3973(2) 0.50172(18) 0.47166(14) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.1346(2) 0.39048(19) 0.57170(13) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.1644(3) 0.2542(2) 0.59270(15) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.215586 0.196538 0.547636 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1175(3) 0.2045(2) 0.68121(16) 0.0236(4) Uani 1 1 d . . . . .
H10 H 0.135669 0.111643 0.696718 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0441(3) 0.2900(2) 0.74715(16) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.012562 0.255312 0.807472 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0167(3) 0.4260(2) 0.72518(15) 0.0229(4) Uani 1 1 d . . . . .
H12 H -0.032791 0.483851 0.770765 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0610(2) 0.4776(2) 0.63717(15) 0.0192(4) Uani 1 1 d . . . . .
H13 H 0.041838 0.570345 0.621680 0.023 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 O1 1.4490(14) . ?
S1 N1 1.5470(18) . ?
S1 C7 1.7298(17) . ?
S1 C8 1.7552(19) . ?
O2 C1 1.233(2) . ?
N1 C1 1.378(2) . ?
N2 C1 1.379(2) . ?
N2 C2 1.389(2) . ?
N2 H2 0.8800 . ?
C2 C7 1.398(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.393(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O1 S1 N1 117.39(9) . . ?
O1 S1 C7 109.58(8) . . ?
N1 S1 C7 107.73(9) . . ?
O1 S1 C8 107.87(9) . . ?
N1 S1 C8 105.97(9) . . ?
C7 S1 C8 107.93(9) . . ?
C1 N1 S1 123.92(14) . . ?
C1 N2 C2 125.55(16) . . ?
C1 N2 H2 117.2 . . ?
C2 N2 H2 117.2 . . ?
O2 C1 N1 120.16(17) . . ?
O2 C1 N2 120.07(17) . . ?
N1 C1 N2 119.76(17) . . ?
N2 C2 C7 122.08(17) . . ?
N2 C2 C3 120.06(17) . . ?
C7 C2 C3 117.84(17) . . ?
C4 C3 C2 120.10(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.59(17) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.21(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 119.23(18) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 122.00(16) . . ?
C2 C7 S1 116.78(14) . . ?
C6 C7 S1 121.01(14) . . ?
C9 C8 C13 121.83(17) . . ?
C9 C8 S1 120.46(15) . . ?
C13 C8 S1 117.67(15) . . ?
C10 C9 C8 118.45(19) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 118.61(19) . . ?
C12 C13 H13 120.7 . . ?
C8 C13 H13 120.7 . . ?

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
O1 S1 N1 C1 101.12(17) . . . . ?
C7 S1 N1 C1 -23.06(19) . . . . ?
C8 S1 N1 C1 -138.37(16) . . . . ?
S1 N1 C1 O2 -167.62(15) . . . . ?
S1 N1 C1 N2 13.4(3) . . . . ?
C2 N2 C1 O2 -174.46(18) . . . . ?
C2 N2 C1 N1 4.5(3) . . . . ?
C1 N2 C2 C7 -7.7(3) . . . . ?
C1 N2 C2 C3 173.80(18) . . . . ?
N2 C2 C3 C4 179.81(18) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
N2 C2 C7 C6 179.92(17) . . . . ?
C3 C2 C7 C6 -1.5(3) . . . . ?
N2 C2 C7 S1 -5.3(2) . . . . ?
C3 C2 C7 S1 173.23(14) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C6 C7 S1 -174.33(14) . . . . ?
O1 S1 C7 C2 -110.28(15) . . . . ?
N1 S1 C7 C2 18.50(17) . . . . ?
C8 S1 C7 C2 132.51(15) . . . . ?
O1 S1 C7 C6 64.52(17) . . . . ?
N1 S1 C7 C6 -166.71(16) . . . . ?
C8 S1 C7 C6 -52.69(18) . . . . ?
O1 S1 C8 C9 159.83(16) . . . . ?
N1 S1 C8 C9 33.32(19) . . . . ?
C7 S1 C8 C9 -81.86(18) . . . . ?
O1 S1 C8 C13 -22.43(17) . . . . ?
N1 S1 C8 C13 -148.94(15) . . . . ?
C7 S1 C8 C13 95.88(16) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
S1 C8 C9 C10 178.32(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C8 -0.4(3) . . . . ?
C9 C8 C13 C12 -0.1(3) . . . . ?
S1 C8 C13 C12 -177.83(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.88 2.36 3.058(2) 136.2 4 yes
C3 H3 O2 0.95 2.55 3.266(3) 132.3 4 yes

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053

