# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_shx97
_database_code_depnum_ccdc_archive 'CCDC 2169421'
loop_
_audit_author_name
_audit_author_address
'Jie-Ping Wan'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 F N2 O3 S'
_chemical_formula_sum            'C12 H13 F N2 O3 S'
_chemical_formula_weight         284.30

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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                   8.0016(16)
_cell_length_b                   9.3863(19)
_cell_length_c                   18.181(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.48(3)
_cell_angle_gamma                90
_cell_volume                     1353.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8572
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10299
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.133
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2385
_reflns_number_gt                1890
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0447P)²+0.2112P] 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         2385
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.45755(7) 0.77942(6) 0.17662(2) 0.0430(2) Uani 1 1 d . . . . .
N1 N 0.5629(2) 0.82239(18) 0.04642(8) 0.0391(4) Uani 1 1 d . . . . .
N2 N 0.3995(2) 1.0035(2) 0.08723(9) 0.0539(5) Uani 1 1 d . . . . .
H2A H 0.405352 1.054404 0.048314 0.065 Uiso 1 1 calc R U . . .
H2B H 0.343927 1.033947 0.121494 0.065 Uiso 1 1 calc R U . . .
F1 F 1.02361(19) 0.06871(17) 0.11501(8) 0.0824(5) Uani 1 1 d . . . . .
O1 O 0.66351(17) 0.57156(15) 0.25606(6) 0.0429(4) Uani 1 1 d . . . . .
O2 O 0.41039(16) 0.54201(15) 0.09316(6) 0.0416(4) Uani 1 1 d . . . . .
O3 O 0.80636(16) 0.71175(15) 0.11004(7) 0.0429(4) Uani 1 1 d . . . . .
C1 C 0.7093(3) 0.3431(2) 0.09939(10) 0.0462(5) Uani 1 1 d . . . . .
H1B H 0.622084 0.376715 0.064946 0.055 Uiso 1 1 calc R U . . .
C2 C 0.8022(3) 0.2266(2) 0.08218(12) 0.0528(6) Uani 1 1 d . . . . .
H2C H 0.777093 0.179985 0.036945 0.063 Uiso 1 1 calc R U . . .
C3 C 0.9311(3) 0.1816(3) 0.13294(12) 0.0523(6) Uani 1 1 d . . . . .
C4 C 0.9720(3) 0.2455(3) 0.20101(12) 0.0546(6) Uani 1 1 d . . . . .
H4A H 1.061349 0.212250 0.234442 0.066 Uiso 1 1 calc R U . . .
C5 C 0.8775(2) 0.3592(2) 0.21812(10) 0.0440(5) Uani 1 1 d . . . . .
H5A H 0.902188 0.402943 0.264150 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7450(2) 0.4109(2) 0.16786(9) 0.0341(4) Uani 1 1 d . . . . .
C7 C 0.6517(2) 0.5357(2) 0.19099(9) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.5398(2) 0.6248(2) 0.13266(9) 0.0330(4) Uani 1 1 d . . . . .
C9 C 0.6404(2) 0.6908(2) 0.07349(9) 0.0349(5) Uani 1 1 d . . . . .
H9A H 0.642661 0.623940 0.032234 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4764(2) 0.8779(2) 0.09443(9) 0.0379(5) Uani 1 1 d . . . . .
C11 C 0.3010(3) 0.4719(3) 0.13842(12) 0.0612(7) Uani 1 1 d . . . . .
H11A H 0.217293 0.418374 0.107359 0.092 Uiso 1 1 calc R U . . .
H11B H 0.365936 0.408706 0.172464 0.092 Uiso 1 1 calc R U . . .
H11C H 0.246637 0.541848 0.165673 0.092 Uiso 1 1 calc R U . . .
C12 C 0.9264(3) 0.7372(3) 0.06070(14) 0.0664(7) Uani 1 1 d . . . . .
H12A H 1.035660 0.750430 0.088579 0.100 Uiso 1 1 calc R U . . .
H12B H 0.929441 0.657063 0.028063 0.100 Uiso 1 1 calc R U . . .
H12C H 0.895377 0.821179 0.032033 0.100 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 1.7802(18) . ?
S1 C8 1.8206(19) . ?
N1 C10 1.292(2) . ?
N1 C9 1.440(2) . ?
N2 C10 1.328(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F1 C3 1.356(2) . ?
O1 C7 1.222(2) . ?
O2 C8 1.414(2) . ?
O2 C11 1.437(3) . ?
O3 C12 1.417(3) . ?
O3 C9 1.419(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.394(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.359(3) . ?
C2 H2C 0.9300 . ?
C3 C4 1.376(3) . ?
C4 C5 1.367(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.479(3) . ?
C7 C8 1.542(2) . ?
C8 C9 1.554(2) . ?
C9 H9A 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 88.31(9) . . ?
C10 N1 C9 111.08(14) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 O2 C11 114.92(14) . . ?
C12 O3 C9 113.39(15) . . ?
C2 C1 C6 120.66(18) . . ?
C2 C1 H1B 119.7 . . ?
C6 C1 H1B 119.7 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2C 120.8 . . ?
C1 C2 H2C 120.8 . . ?
F1 C3 C2 118.0(2) . . ?
F1 C3 C4 118.91(19) . . ?
C2 C3 C4 123.1(2) . . ?
C5 C4 C3 118.11(19) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C5 C6 121.24(19) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C1 118.46(18) . . ?
C5 C6 C7 117.28(16) . . ?
C1 C6 C7 124.26(16) . . ?
O1 C7 C6 121.00(16) . . ?
O1 C7 C8 118.76(17) . . ?
C6 C7 C8 120.22(14) . . ?
O2 C8 C7 111.86(15) . . ?
O2 C8 C9 106.17(13) . . ?
C7 C8 C9 112.68(15) . . ?
O2 C8 S1 112.24(12) . . ?
C7 C8 S1 109.95(12) . . ?
C9 C8 S1 103.63(13) . . ?
O3 C9 N1 112.10(16) . . ?
O3 C9 C8 105.58(13) . . ?
N1 C9 C8 109.87(14) . . ?
O3 C9 H9A 109.7 . . ?
N1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N1 C10 N2 124.98(17) . . ?
N1 C10 S1 117.96(15) . . ?
N2 C10 S1 117.06(14) . . ?
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 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.050



