# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2245830'
loop_
_audit_author_name
_audit_author_address
'Dandan Li'
;Xuchang University
China
;
_audit_update_record             
;
2023-03-02 deposited with the CCDC.	2023-05-16 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 H9 N O2 S'
_chemical_formula_weight         219.25

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                   12.545(5)
_cell_length_b                   3.9268(16)
_cell_length_c                   21.018(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.758(6)
_cell_angle_gamma                90
_cell_volume                     991.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2603
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.64

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.937
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4629
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1748
_reflns_number_gt                1555
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0707P)²+0.1631P] 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         1748
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_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 0.48650(3) 0.48001(10) 0.32627(2) 0.03355(18) Uani 1 1 d . . . . .
O2 O 0.69816(10) 0.5921(4) 0.39855(6) 0.0444(3) Uani 1 1 d . . . . .
O1 O 0.24743(11) 0.5010(4) 0.27168(6) 0.0515(4) Uani 1 1 d . . . . .
N1 N 0.55959(11) 0.7639(4) 0.44115(6) 0.0373(3) Uani 1 1 d . . . . .
C6 C 0.18825(13) 0.6758(4) 0.36312(7) 0.0313(4) Uani 1 1 d . . . . .
C7 C 0.27379(14) 0.5918(4) 0.32982(7) 0.0332(4) Uani 1 1 d . . . . .
C8 C 0.39146(13) 0.6211(4) 0.36575(7) 0.0293(4) Uani 1 1 d . . . . .
C5 C 0.08932(14) 0.8188(5) 0.32478(8) 0.0378(4) Uani 1 1 d . . . . .
H5 H 0.0802 0.8669 0.2802 0.045 Uiso 1 1 calc R U . . .
C9 C 0.44659(13) 0.7641(4) 0.42481(7) 0.0331(4) Uani 1 1 d . . . . .
H9 H 0.4089 0.8578 0.4528 0.040 Uiso 1 1 calc R U . . .
C1 C 0.20018(14) 0.6024(5) 0.42935(8) 0.0379(4) Uani 1 1 d . . . . .
H1 H 0.2658 0.5053 0.4556 0.045 Uiso 1 1 calc R U . . .
C4 C 0.00497(15) 0.8896(5) 0.35221(10) 0.0448(4) Uani 1 1 d . . . . .
H4 H -0.0610 0.9861 0.3263 0.054 Uiso 1 1 calc R U . . .
C10 C 0.59092(13) 0.6210(4) 0.39390(8) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.01792(15) 0.8178(5) 0.41819(9) 0.0468(5) Uani 1 1 d . . . . .
H3 H -0.0391 0.8673 0.4368 0.056 Uiso 1 1 calc R U . . .
C2 C 0.11447(15) 0.6740(5) 0.45622(9) 0.0459(5) Uani 1 1 d . . . . .
H2 H 0.1225 0.6240 0.5006 0.055 Uiso 1 1 calc R U . . .
C11 C 0.72611(17) 0.4262(5) 0.34477(10) 0.0492(5) Uani 1 1 d . . . . .
H11A H 0.6966 0.5546 0.3047 0.074 Uiso 1 1 calc R U . . .
H11B H 0.6949 0.2011 0.3391 0.074 Uiso 1 1 calc R U . . .
H11C H 0.8056 0.4116 0.3545 0.074 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 C10 1.7232(17) . ?
S1 C8 1.7285(16) . ?
O2 C10 1.325(2) . ?
O2 C11 1.433(2) . ?
O1 C7 1.223(2) . ?
N1 C10 1.297(2) . ?
N1 C9 1.359(2) . ?
C6 C1 1.387(2) . ?
C6 C5 1.389(2) . ?
C6 C7 1.478(2) . ?
C7 C8 1.456(2) . ?
C8 C9 1.356(2) . ?
C5 C4 1.372(3) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C1 C2 1.380(2) . ?
C1 H1 0.9300 . ?
C4 C3 1.378(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.366(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C10 S1 C8 88.08(8) . . ?
C10 O2 C11 117.05(14) . . ?
C10 N1 C9 109.34(14) . . ?
C1 C6 C5 119.09(15) . . ?
C1 C6 C7 123.11(14) . . ?
C5 C6 C7 117.71(14) . . ?
O1 C7 C8 118.87(15) . . ?
O1 C7 C6 120.93(15) . . ?
C8 C7 C6 120.19(14) . . ?
C9 C8 C7 132.89(15) . . ?
C9 C8 S1 109.38(12) . . ?
C7 C8 S1 117.54(12) . . ?
C4 C5 C6 120.46(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N1 C9 C8 116.78(14) . . ?
N1 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C2 C1 C6 119.82(16) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C5 C4 C3 120.00(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C10 O2 120.40(15) . . ?
N1 C10 S1 116.41(13) . . ?
O2 C10 S1 123.19(12) . . ?
C2 C3 C4 120.05(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 120.58(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C1 C6 C7 O1 143.99(18) . . . . ?
C5 C6 C7 O1 -32.6(2) . . . . ?
C1 C6 C7 C8 -36.9(2) . . . . ?
C5 C6 C7 C8 146.50(16) . . . . ?
O1 C7 C8 C9 167.31(18) . . . . ?
C6 C7 C8 C9 -11.8(3) . . . . ?
O1 C7 C8 S1 -6.9(2) . . . . ?
C6 C7 C8 S1 173.93(12) . . . . ?
C10 S1 C8 C9 1.00(13) . . . . ?
C10 S1 C8 C7 176.54(14) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C7 C6 C5 C4 177.36(16) . . . . ?
C10 N1 C9 C8 0.4(2) . . . . ?
C7 C8 C9 N1 -175.60(17) . . . . ?
S1 C8 C9 N1 -1.01(19) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C7 C6 C1 C2 -176.96(17) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C9 N1 C10 O2 179.77(15) . . . . ?
C9 N1 C10 S1 0.49(19) . . . . ?
C11 O2 C10 N1 179.03(16) . . . . ?
C11 O2 C10 S1 -1.8(2) . . . . ?
C8 S1 C10 N1 -0.90(14) . . . . ?
C8 S1 C10 O2 179.85(15) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044

