# 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_JXC041
_database_code_depnum_ccdc_archive 'CCDC 2236179'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2023-01-15 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H13 Cl F3 N3 O2 S'
_chemical_formula_sum            'C17 H13 Cl F3 N3 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         415.81

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'
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'
Cl Cl 0.1484 0.1585 '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                   8.0656(3)
_cell_length_b                   8.5494(3)
_cell_length_c                   13.9078(6)
_cell_angle_alpha                85.0509(15)
_cell_angle_beta                 86.9189(14)
_cell_angle_gamma                79.3578(14)
_cell_volume                     938.32(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.742
_cell_measurement_theta_max      27.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.361
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            18454
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0365
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         27.952
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4468
_reflns_number_gt                4003
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0633P)²+0.8374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4468
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Cl Cl 0.62021(7) 0.11275(6) 0.07100(4) 0.03171(15) Uani 1 1 d . . . . .
S S 0.26858(5) 0.89642(5) 0.53702(3) 0.01605(12) Uani 1 1 d . . . . .
F1 F 0.14475(18) 0.02101(17) 0.26083(9) 0.0366(3) Uani 1 1 d . . . . .
F2 F 0.37689(19) -0.11105(15) 0.20588(14) 0.0495(4) Uani 1 1 d . . . . .
F3 F 0.2113(2) 0.04443(18) 0.11018(9) 0.0424(4) Uani 1 1 d . . . . .
O1 O 0.11440(16) 0.87999(17) 0.59005(9) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.41922(16) 0.89054(17) 0.58893(9) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.30133(19) 0.26647(17) 0.27861(11) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.40658(19) 0.37395(17) 0.27001(11) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.2350(2) 1.06610(19) 0.47445(11) 0.0191(3) Uani 1 1 d . . . . .
H3A H 0.144(3) 1.080(3) 0.4439(18) 0.028(6) Uiso 1 1 d . . . . .
H3B H 0.324(4) 1.082(3) 0.4426(19) 0.030(6) Uiso 1 1 d . . . . .
C1 C 0.5318(2) 0.3414(2) 0.20021(13) 0.0187(3) Uani 1 1 d . . . . .
C2 C 0.5041(2) 0.2051(2) 0.16308(13) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.3613(2) 0.1639(2) 0.21336(13) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.3768(2) 0.5007(2) 0.33316(12) 0.0178(3) Uani 1 1 d . . . . .
C5 C 0.2113(2) 0.5542(2) 0.36616(15) 0.0265(4) Uani 1 1 d . . . . .
H5A H 0.121677 0.508204 0.345971 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1787(2) 0.6751(3) 0.42866(15) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.066524 0.712244 0.451669 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3107(2) 0.7417(2) 0.45746(12) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.4755(2) 0.6882(2) 0.42427(13) 0.0202(3) Uani 1 1 d . . . . .
H8A H 0.564980 0.735203 0.443738 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5087(2) 0.5658(2) 0.36255(13) 0.0208(4) Uani 1 1 d . . . . .
H9A H 0.621273 0.527167 0.340665 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6622(2) 0.4370(2) 0.16913(13) 0.0185(3) Uani 1 1 d . . . . .
C11 C 0.6200(3) 0.5820(2) 0.11504(16) 0.0269(4) Uani 1 1 d . . . . .
H11A H 0.505930 0.620877 0.099036 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7439(3) 0.6702(2) 0.08428(17) 0.0316(5) Uani 1 1 d . . . . .
H12A H 0.713465 0.769629 0.047729 0.038 Uiso 1 1 calc R U . . .
C13 C 0.9114(3) 0.6154(3) 0.10615(15) 0.0277(4) Uani 1 1 d . . . . .
C14 C 0.9527(3) 0.4688(3) 0.15853(16) 0.0294(4) Uani 1 1 d . . . . .
H14A H 1.067207 0.428674 0.172995 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8298(3) 0.3796(2) 0.19027(15) 0.0262(4) Uani 1 1 d . . . . .
H15A H 0.860467 0.279782 0.226288 0.031 Uiso 1 1 calc R U . . .
C16 C 1.0461(3) 0.7120(3) 0.0742(2) 0.0443(6) Uani 1 1 d . . . . .
H16A H 1.155818 0.654486 0.096122 0.066 Uiso 1 1 calc R U . . .
H16B H 1.050351 0.728827 0.003577 0.066 Uiso 1 1 calc R U . . .
H16C H 1.019596 0.815527 0.102144 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2731(3) 0.0293(2) 0.19849(14) 0.0230(4) Uani 1 1 d . . . . .


_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
Cl C2 1.7069(18) . ?
S O1 1.4346(13) . ?
S O2 1.4372(13) . ?
S N3 1.6117(16) . ?
S C7 1.7704(18) . ?
F1 C17 1.322(2) . ?
F2 C17 1.330(2) . ?
F3 C17 1.337(2) . ?
N1 C3 1.327(2) . ?
N1 N2 1.356(2) . ?
N2 C1 1.370(2) . ?
N2 C4 1.431(2) . ?
N3 H3A 0.85(3) . ?
N3 H3B 0.85(3) . ?
C1 C2 1.374(2) . ?
C1 C10 1.473(2) . ?
C2 C3 1.400(2) . ?
C3 C17 1.494(2) . ?
C4 C9 1.384(2) . ?
C4 C5 1.395(3) . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.391(2) . ?
C8 C9 1.389(2) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.389(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(3) . ?
C13 C16 1.509(3) . ?
C14 C15 1.390(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 S O2 119.12(8) . . ?
O1 S N3 107.22(8) . . ?
O2 S N3 106.96(8) . . ?
O1 S C7 106.97(8) . . ?
O2 S C7 107.29(8) . . ?
N3 S C7 109.01(8) . . ?
C3 N1 N2 104.47(14) . . ?
N1 N2 C1 112.83(14) . . ?
N1 N2 C4 118.15(14) . . ?
C1 N2 C4 129.01(15) . . ?
S N3 H3A 112.2(17) . . ?
S N3 H3B 110.6(18) . . ?
H3A N3 H3B 117(2) . . ?
N2 C1 C2 105.00(15) . . ?
N2 C1 C10 127.07(16) . . ?
C2 C1 C10 127.88(16) . . ?
C1 C2 C3 106.27(16) . . ?
C1 C2 Cl 125.33(15) . . ?
C3 C2 Cl 128.37(14) . . ?
N1 C3 C2 111.43(16) . . ?
N1 C3 C17 120.28(16) . . ?
C2 C3 C17 128.23(17) . . ?
C9 C4 C5 120.85(16) . . ?
C9 C4 N2 121.00(15) . . ?
C5 C4 N2 118.14(15) . . ?
C6 C5 C4 119.50(17) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C7 119.74(17) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C6 C7 C8 120.60(16) . . ?
C6 C7 S 119.62(13) . . ?
C8 C7 S 119.78(13) . . ?
C9 C8 C7 119.78(16) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C4 C9 C8 119.53(16) . . ?
C4 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C11 C10 C15 119.39(17) . . ?
C11 C10 C1 120.40(17) . . ?
C15 C10 C1 120.15(16) . . ?
C12 C11 C10 120.21(18) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 120.95(19) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C12 C13 C14 118.33(18) . . ?
C12 C13 C16 121.1(2) . . ?
C14 C13 C16 120.5(2) . . ?
C13 C14 C15 121.34(19) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C10 C15 C14 119.76(18) . . ?
C10 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 C17 F2 107.60(16) . . ?
F1 C17 F3 106.91(17) . . ?
F2 C17 F3 106.27(17) . . ?
F1 C17 C3 112.68(15) . . ?
F2 C17 C3 111.89(17) . . ?
F3 C17 C3 111.13(15) . . ?

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
C3 N1 N2 C1 0.20(19) . . . . ?
C3 N1 N2 C4 -178.79(15) . . . . ?
N1 N2 C1 C2 -0.3(2) . . . . ?
C4 N2 C1 C2 178.60(16) . . . . ?
N1 N2 C1 C10 177.07(16) . . . . ?
C4 N2 C1 C10 -4.1(3) . . . . ?
N2 C1 C2 C3 0.2(2) . . . . ?
C10 C1 C2 C3 -177.10(17) . . . . ?
N2 C1 C2 Cl 178.26(14) . . . . ?
C10 C1 C2 Cl 1.0(3) . . . . ?
N2 N1 C3 C2 -0.1(2) . . . . ?
N2 N1 C3 C17 -177.64(16) . . . . ?
C1 C2 C3 N1 -0.1(2) . . . . ?
Cl C2 C3 N1 -178.07(14) . . . . ?
C1 C2 C3 C17 177.24(18) . . . . ?
Cl C2 C3 C17 -0.7(3) . . . . ?
N1 N2 C4 C9 149.15(17) . . . . ?
C1 N2 C4 C9 -29.7(3) . . . . ?
N1 N2 C4 C5 -29.4(2) . . . . ?
C1 N2 C4 C5 151.82(19) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
N2 C4 C5 C6 178.99(18) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 S 179.85(16) . . . . ?
O1 S C7 C6 24.46(18) . . . . ?
O2 S C7 C6 153.35(16) . . . . ?
N3 S C7 C6 -91.16(17) . . . . ?
O1 S C7 C8 -155.63(15) . . . . ?
O2 S C7 C8 -26.75(17) . . . . ?
N3 S C7 C8 88.74(16) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
S C7 C8 C9 179.40(14) . . . . ?
C5 C4 C9 C8 -1.2(3) . . . . ?
N2 C4 C9 C8 -179.70(16) . . . . ?
C7 C8 C9 C4 1.3(3) . . . . ?
N2 C1 C10 C11 -72.2(3) . . . . ?
C2 C1 C10 C11 104.5(2) . . . . ?
N2 C1 C10 C15 110.5(2) . . . . ?
C2 C1 C10 C15 -72.8(3) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?
C1 C10 C11 C12 -178.73(19) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C16 -179.0(2) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C16 C13 C14 C15 178.7(2) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C1 C10 C15 C14 178.36(18) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
N1 C3 C17 F1 -4.9(3) . . . . ?
C2 C3 C17 F1 177.92(18) . . . . ?
N1 C3 C17 F2 -126.35(19) . . . . ?
C2 C3 C17 F2 56.5(3) . . . . ?
N1 C3 C17 F3 115.03(19) . . . . ?
C2 C3 C17 F3 -62.1(3) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.060

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

