# 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_exp_19293
_database_code_depnum_ccdc_archive 'CCDC 2133059'
loop_
_audit_author_name
_audit_author_address
'Long-Wu Ye'
;Xiamen University
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N O S'
_chemical_formula_weight         204.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.7021(10)
_cell_length_b                   15.1512(11)
_cell_length_c                   11.1435(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.894(6)
_cell_angle_gamma                90
_cell_volume                     2308.1(3)
_cell_formula_units_Z            10
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1070
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11606
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         29.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5793
_reflns_number_gt                4273
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1833P)²+2.5103P] 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         5793
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2655
_refine_ls_wR_factor_gt          0.2357
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          2.746
_refine_ls_shift/su_mean         0.049

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
S001 S 0.09132(5) 0.51570(5) 0.29218(6) 0.0317(2) Uani 1 1 d . . . . .
O002 O 0.00820(15) 0.53846(15) 0.3571(2) 0.0373(5) Uani 1 1 d . . . . .
O003 O 0.09559(19) 0.54029(17) 0.1697(2) 0.0451(6) Uani 1 1 d . . . . .
O004 O 0.30829(17) 0.52849(16) 0.2447(2) 0.0427(6) Uani 1 1 d . . . . .
N005 N 0.18462(18) 0.56236(17) 0.3704(2) 0.0325(5) Uani 1 1 d . . . . .
C006 C 0.0783(2) 0.3577(2) 0.4042(3) 0.0332(6) Uani 1 1 d . . . . .
H006 H 0.0441 0.3876 0.4609 0.040 Uiso 1 1 calc R U . . .
C007 C 0.2787(2) 0.62982(18) 0.5201(2) 0.0289(6) Uani 1 1 d . . . . .
C008 C 0.2466(2) 0.6713(2) 0.7334(3) 0.0322(6) Uani 1 1 d . . . . .
C009 C 0.1766(2) 0.60046(19) 0.4899(2) 0.0296(6) Uani 1 1 d . . . . .
H00A H 0.1561 0.5567 0.5466 0.035 Uiso 1 1 calc R U . . .
H00B H 0.1313 0.6497 0.4875 0.035 Uiso 1 1 calc R U . . .
C00A C 0.1127(2) 0.4025(2) 0.3063(2) 0.0300(6) Uani 1 1 d . . . . .
C00B C 0.3389(2) 0.60605(19) 0.4352(3) 0.0321(6) Uani 1 1 d . . . . .
C00C C 0.3097(2) 0.6800(2) 0.6293(3) 0.0329(6) Uani 1 1 d . . . . .
C00D C 0.1646(2) 0.3585(2) 0.2216(3) 0.0388(7) Uani 1 1 d . . . . .
H00D H 0.1877 0.3886 0.1565 0.047 Uiso 1 1 calc R U . . .
C00E C 0.4454(2) 0.6165(2) 0.4494(3) 0.0353(7) Uani 1 1 d . . . . .
C00F C 0.2827(2) 0.5612(2) 0.3364(3) 0.0334(6) Uani 1 1 d . . . . .
C00G C 0.0956(2) 0.2684(2) 0.4157(3) 0.0383(7) Uani 1 1 d . . . . .
H00G H 0.0722 0.2380 0.4803 0.046 Uiso 1 1 calc R U . . .
C00H C 0.1636(2) 0.7237(2) 0.7390(3) 0.0368(7) Uani 1 1 d . . . . .
H00H H 0.1502 0.7672 0.6813 0.044 Uiso 1 1 calc R U . . .
C00I C 0.1474(2) 0.2229(2) 0.3327(3) 0.0397(7) Uani 1 1 d . . . . .
C00J C 0.2661(3) 0.6077(2) 0.8219(3) 0.0399(7) Uani 1 1 d . . . . .
H00J H 0.3212 0.5721 0.8194 0.048 Uiso 1 1 calc R U . . .
C00K C 0.1200(3) 0.6483(2) 0.9171(3) 0.0426(8) Uani 1 1 d . . . . .
H00K H 0.0771 0.6399 0.9772 0.051 Uiso 1 1 calc R U . . .
C00L C 0.1813(3) 0.2686(2) 0.2365(3) 0.0432(8) Uani 1 1 d . . . . .
H00L H 0.2161 0.2385 0.1805 0.052 Uiso 1 1 calc R U . . .
C00M C 0.1008(2) 0.7117(2) 0.8300(3) 0.0408(7) Uani 1 1 d . . . . .
H00M H 0.0452 0.7468 0.8323 0.049 Uiso 1 1 calc R U . . .
C00N C 0.4848(2) 0.6517(2) 0.5590(3) 0.0412(7) Uani 1 1 d . . . . .
C00O C 0.2033(3) 0.5973(2) 0.9144(3) 0.0450(8) Uani 1 1 d . . . . .
H00O H 0.2176 0.5558 0.9746 0.054 Uiso 1 1 calc R U . . .
C00P C 0.4217(2) 0.6922(2) 0.6469(3) 0.0445(8) Uani 1 1 d . . . . .
H00P H 0.4491 0.6942 0.7304 0.053 Uiso 1 1 calc R U . . .
C00Q C 0.5080(3) 0.5860(2) 0.3654(4) 0.0488(9) Uani 1 1 d . . . . .
H00Q H 0.4823 0.5628 0.2927 0.059 Uiso 1 1 calc R U . . .
C00R C 0.3571(3) 0.7680(2) 0.6070(3) 0.0456(8) Uani 1 1 d . . . . .
H00C H 0.3589 0.7875 0.5242 0.055 Uiso 1 1 calc R U . . .
H00E H 0.3483 0.8149 0.6645 0.055 Uiso 1 1 calc R U . . .
C00S C 0.6089(3) 0.5899(3) 0.3897(5) 0.0580(11) Uani 1 1 d . . . . .
H00S H 0.6504 0.5710 0.3322 0.070 Uiso 1 1 calc R U . . .
C00T C 0.5862(3) 0.6514(3) 0.5827(4) 0.0548(10) Uani 1 1 d . . . . .
H00T H 0.6130 0.6717 0.6565 0.066 Uiso 1 1 calc R U . . .
C00U C 0.5351(4) 0.9837(5) 0.4731(5) 0.090(2) Uani 1 1 d . . . . .
H00U H 0.5693 1.0227 0.4270 0.108 Uiso 1 1 calc R U . . .
C00V C 0.1650(3) 0.1254(3) 0.3476(4) 0.0605(11) Uani 1 1 d . . . . .
H00F H 0.2139 0.1157 0.4120 0.091 Uiso 1 1 calc R U . . .
H00I H 0.1871 0.1016 0.2744 0.091 Uiso 1 1 calc R U . . .
H00N H 0.1053 0.0969 0.3659 0.091 Uiso 1 1 calc R U . . .
C00W C 0.6473(3) 0.6212(3) 0.4970(5) 0.0600(11) Uani 1 1 d . . . . .
H00W H 0.7147 0.6225 0.5132 0.072 Uiso 1 1 calc R U . . .
C00X C 0.5802(4) 0.8618(4) 0.4754(6) 0.101(2) Uani 1 1 d . . . . .
H00R H 0.6051 0.8476 0.3993 0.152 Uiso 1 1 calc R U . . .
H00V H 0.5267 0.8233 0.4900 0.152 Uiso 1 1 calc R U . . .
H00X H 0.6312 0.8545 0.5382 0.152 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
S001 O003 1.420(2) . ?
S001 O002 1.432(2) . ?
S001 N005 1.656(3) . ?
S001 C00A 1.746(3) . ?
O004 C00F 1.209(4) . ?
N005 C00F 1.420(4) . ?
N005 C009 1.462(3) . ?
C006 C00G 1.378(4) . ?
C006 C00A 1.394(4) . ?
C006 H006 0.9300 . ?
C007 C00B 1.345(4) . ?
C007 C00C 1.473(4) . ?
C007 C009 1.485(4) . ?
C008 C00J 1.391(4) . ?
C008 C00H 1.393(4) . ?
C008 C00C 1.498(4) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C00A C00D 1.389(4) . ?
C00B C00E 1.466(4) . ?
C00B C00F 1.467(4) . ?
C00C C00R 1.512(4) . ?
C00C C00P 1.546(4) . ?
C00D C00L 1.389(5) . ?
C00D H00D 0.9300 . ?
C00E C00Q 1.391(5) . ?
C00E C00N 1.407(5) . ?
C00G C00I 1.386(5) . ?
C00G H00G 0.9300 . ?
C00H C00M 1.386(4) . ?
C00H H00H 0.9300 . ?
C00I C00L 1.383(5) . ?
C00I C00V 1.503(5) . ?
C00J C00O 1.397(5) . ?
C00J H00J 0.9300 . ?
C00K C00O 1.380(5) . ?
C00K C00M 1.379(5) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00T 1.395(5) . ?
C00N C00P 1.482(5) . ?
C00O H00O 0.9300 . ?
C00P C00R 1.500(5) . ?
C00P H00P 0.9800 . ?
C00Q C00S 1.393(5) . ?
C00Q H00Q 0.9300 . ?
C00R H00C 0.9700 . ?
C00R H00E 0.9700 . ?
C00S C00W 1.358(7) . ?
C00S H00S 0.9300 . ?
C00T C00W 1.390(6) . ?
C00T H00T 0.9300 . ?
C00U C00U 1.268(12) 3_676 ?
C00U C00X 1.947(10) . ?
C00U H00U 0.9300 . ?
C00V H00F 0.9601 . ?
C00V H00I 0.9601 . ?
C00V H00N 0.9601 . ?
C00W H00W 0.9300 . ?
C00X H00R 0.9625 . ?
C00X H00V 0.9625 . ?
C00X H00X 0.9625 . ?

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
O003 S001 O002 120.58(15) . . ?
O003 S001 N005 108.25(14) . . ?
O002 S001 N005 104.08(13) . . ?
O003 S001 C00A 109.06(14) . . ?
O002 S001 C00A 109.01(14) . . ?
N005 S001 C00A 104.66(13) . . ?
C00F N005 C009 112.2(2) . . ?
C00F N005 S001 124.4(2) . . ?
C009 N005 S001 123.00(19) . . ?
C00G C006 C00A 119.0(3) . . ?
C00G C006 H006 120.5 . . ?
C00A C006 H006 120.5 . . ?
C00B C007 C00C 124.3(3) . . ?
C00B C007 C009 112.0(3) . . ?
C00C C007 C009 123.8(2) . . ?
C00J C008 C00H 118.7(3) . . ?
C00J C008 C00C 121.1(3) . . ?
C00H C008 C00C 120.0(3) . . ?
N005 C009 C007 101.3(2) . . ?
N005 C009 H00A 111.5 . . ?
C007 C009 H00A 111.5 . . ?
N005 C009 H00B 111.5 . . ?
C007 C009 H00B 111.5 . . ?
H00A C009 H00B 109.3 . . ?
C00D C00A C006 120.9(3) . . ?
C00D C00A S001 120.0(2) . . ?
C006 C00A S001 119.0(2) . . ?
C007 C00B C00E 123.3(3) . . ?
C007 C00B C00F 109.6(3) . . ?
C00E C00B C00F 126.8(3) . . ?
C007 C00C C008 116.5(2) . . ?
C007 C00C C00R 115.0(3) . . ?
C008 C00C C00R 118.8(3) . . ?
C007 C00C C00P 113.2(3) . . ?
C008 C00C C00P 122.1(3) . . ?
C00R C00C C00P 58.7(2) . . ?
C00L C00D C00A 118.4(3) . . ?
C00L C00D H00D 120.8 . . ?
C00A C00D H00D 120.8 . . ?
C00Q C00E C00N 119.5(3) . . ?
C00Q C00E C00B 123.1(3) . . ?
C00N C00E C00B 117.1(3) . . ?
O004 C00F N005 124.4(3) . . ?
O004 C00F C00B 131.0(3) . . ?
N005 C00F C00B 104.6(2) . . ?
C006 C00G C00I 121.3(3) . . ?
C006 C00G H00G 119.4 . . ?
C00I C00G H00G 119.4 . . ?
C00M C00H C008 120.6(3) . . ?
C00M C00H H00H 119.7 . . ?
C008 C00H H00H 119.7 . . ?
C00G C00I C00L 118.8(3) . . ?
C00G C00I C00V 120.0(3) . . ?
C00L C00I C00V 121.2(3) . . ?
C008 C00J C00O 120.2(3) . . ?
C008 C00J H00J 119.9 . . ?
C00O C00J H00J 119.9 . . ?
C00O C00K C00M 119.6(3) . . ?
C00O C00K H00K 120.2 . . ?
C00M C00K H00K 120.2 . . ?
C00D C00L C00I 121.5(3) . . ?
C00D C00L H00L 119.2 . . ?
C00I C00L H00L 119.2 . . ?
C00K C00M C00H 120.5(3) . . ?
C00K C00M H00M 119.7 . . ?
C00H C00M H00M 119.8 . . ?
C00T C00N C00E 118.8(3) . . ?
C00T C00N C00P 119.6(3) . . ?
C00E C00N C00P 121.5(3) . . ?
C00K C00O C00J 120.3(3) . . ?
C00K C00O H00O 119.8 . . ?
C00J C00O H00O 119.9 . . ?
C00N C00P C00R 118.7(3) . . ?
C00N C00P C00C 119.1(3) . . ?
C00R C00P C00C 59.5(2) . . ?
C00N C00P H00P 116.0 . . ?
C00R C00P H00P 115.9 . . ?
C00C C00P H00P 115.9 . . ?
C00S C00Q C00E 120.3(4) . . ?
C00S C00Q H00Q 119.9 . . ?
C00E C00Q H00Q 119.9 . . ?
C00P C00R C00C 61.8(2) . . ?
C00P C00R H00C 117.6 . . ?
C00C C00R H00C 117.6 . . ?
C00P C00R H00E 117.6 . . ?
C00C C00R H00E 117.6 . . ?
H00C C00R H00E 114.7 . . ?
C00W C00S C00Q 120.4(4) . . ?
C00W C00S H00S 119.8 . . ?
C00Q C00S H00S 119.8 . . ?
C00W C00T C00N 120.6(4) . . ?
C00W C00T H00T 119.7 . . ?
C00N C00T H00T 119.7 . . ?
C00U C00U C00X 127.8(7) 3_676 . ?
C00U C00U H00U 116.0 3_676 . ?
C00X C00U H00U 116.1 . . ?
C00I C00V H00F 109.5 . . ?
C00I C00V H00I 109.5 . . ?
H00F C00V H00I 109.5 . . ?
C00I C00V H00N 109.5 . . ?
H00F C00V H00N 109.5 . . ?
H00I C00V H00N 109.5 . . ?
C00S C00W C00T 120.3(4) . . ?
C00S C00W H00W 119.8 . . ?
C00T C00W H00W 119.8 . . ?
C00U C00X H00R 109.6 . . ?
C00U C00X H00V 109.7 . . ?
H00R C00X H00V 109.3 . . ?
C00U C00X H00X 109.7 . . ?
H00R C00X H00X 109.3 . . ?
H00V C00X H00X 109.3 . . ?

_refine_diff_density_max         1.357
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
