# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_191116e
_audit_block_doi                 10.5517/ccdc.csd.cc241lrk
_database_code_depnum_ccdc_archive 'CCDC 1967748'
loop_
_audit_author_name
_audit_author_address
'Jiangwei Wen'
;Single Crystal Diffraction Testing Center of Liaocheng University, China
China
;
_audit_update_record             
;
2019-11-24 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 F N2 S'
_chemical_formula_weight         272.33

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6772(8)
_cell_length_b                   9.0145(9)
_cell_length_c                   9.9691(9)
_cell_angle_alpha                110.220(4)
_cell_angle_beta                 107.146(3)
_cell_angle_gamma                97.596(2)
_cell_volume                     674.97(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1735
_cell_measurement_theta_min      2.495
_cell_measurement_theta_max      27.853

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9004
_exptl_absorpt_correction_T_max  0.9320
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3379
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2326
_reflns_number_gt                1844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.2402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.0660(2) 0.2474(2) 0.6872(2) 0.0885(6) Uani 1 1 d . . .
N1 N 0.2286(3) 0.2937(2) 0.1672(2) 0.0438(5) Uani 1 1 d . . .
N2 N 0.3075(2) 0.1823(2) 0.3361(2) 0.0443(5) Uani 1 1 d . . .
S1 S 0.51858(9) 0.44457(7) 0.15716(7) 0.0538(2) Uani 1 1 d . . .
C1 C 0.4021(3) 0.3405(3) 0.2276(2) 0.0427(5) Uani 1 1 d . . .
C2 C 0.4464(3) 0.2686(2) 0.3306(2) 0.0404(5) Uani 1 1 d . . .
C3 C 0.1770(3) 0.1989(3) 0.2375(3) 0.0438(5) Uani 1 1 d . . .
C4 C 0.0048(3) 0.1371(3) 0.1975(3) 0.0520(6) Uani 1 1 d . . .
H4 H -0.0318 0.0768 0.2465 0.062 Uiso 1 1 calc R . .
C5 C -0.1090(3) 0.1649(3) 0.0872(3) 0.0565(7) Uani 1 1 d . . .
C6 C -0.0482(4) 0.2593(3) 0.0164(3) 0.0617(7) Uani 1 1 d . . .
H6 H -0.1245 0.2779 -0.0598 0.074 Uiso 1 1 calc R . .
C7 C 0.1157(4) 0.3224(3) 0.0556(3) 0.0564(7) Uani 1 1 d . . .
H7 H 0.1522 0.3846 0.0080 0.068 Uiso 1 1 calc R . .
C8 C -0.2931(4) 0.0963(4) 0.0406(4) 0.0731(9) Uani 1 1 d . . .
H8A H -0.3111 0.0340 0.0981 0.110 Uiso 1 1 calc R . .
H8B H -0.3400 0.0266 -0.0671 0.110 Uiso 1 1 calc R . .
H8C H -0.3459 0.1844 0.0609 0.110 Uiso 1 1 calc R . .
C9 C 0.6123(3) 0.2671(3) 0.4217(2) 0.0403(5) Uani 1 1 d . . .
C10 C 0.6333(3) 0.1247(3) 0.4417(3) 0.0510(6) Uani 1 1 d . . .
H10 H 0.5428 0.0328 0.3945 0.061 Uiso 1 1 calc R . .
C11 C 0.7847(4) 0.1168(3) 0.5297(3) 0.0616(7) Uani 1 1 d . . .
H11 H 0.7974 0.0209 0.5419 0.074 Uiso 1 1 calc R . .
C12 C 0.9159(3) 0.2531(4) 0.5988(3) 0.0584(7) Uani 1 1 d . . .
C13 C 0.9020(3) 0.3967(3) 0.5833(3) 0.0551(6) Uani 1 1 d . . .
H13 H 0.9933 0.4880 0.6319 0.066 Uiso 1 1 calc R . .
C14 C 0.7499(3) 0.4028(3) 0.4943(3) 0.0476(6) Uani 1 1 d . . .
H14 H 0.7389 0.4992 0.4824 0.057 Uiso 1 1 calc R . .
C15 C 0.5174(4) 0.6547(3) 0.2524(3) 0.0601(7) Uani 1 1 d . . .
H15A H 0.4045 0.6640 0.2243 0.090 Uiso 1 1 calc R . .
H15B H 0.5814 0.7232 0.2218 0.090 Uiso 1 1 calc R . .
H15C H 0.5657 0.6887 0.3616 0.090 Uiso 1 1 calc R . .


_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
F1 C12 1.359(3) . ?
N1 C7 1.374(3) . ?
N1 C3 1.386(3) . ?
N1 C1 1.389(3) . ?
N2 C3 1.327(3) . ?
N2 C2 1.373(3) . ?
S1 C1 1.737(2) . ?
S1 C15 1.805(2) . ?
C1 C2 1.384(3) . ?
C2 C9 1.463(3) . ?
C3 C4 1.406(4) . ?
C4 C5 1.364(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.421(4) . ?
C5 C8 1.500(4) . ?
C6 C7 1.343(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.392(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C7 N1 C3 121.4(2) . . ?
C7 N1 C1 131.2(2) . . ?
C3 N1 C1 107.34(19) . . ?
C3 N2 C2 106.03(18) . . ?
C1 S1 C15 103.19(11) . . ?
C2 C1 N1 104.85(19) . . ?
C2 C1 S1 132.3(2) . . ?
N1 C1 S1 122.34(17) . . ?
N2 C2 C1 111.0(2) . . ?
N2 C2 C9 119.37(18) . . ?
C1 C2 C9 129.5(2) . . ?
N2 C3 N1 110.8(2) . . ?
N2 C3 C4 130.5(2) . . ?
N1 C3 C4 118.7(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C8 121.1(3) . . ?
C6 C5 C8 120.8(3) . . ?
C7 C6 C5 122.3(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 N1 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
N1 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.9(2) . . ?
C14 C9 C2 123.4(2) . . ?
C10 C9 C2 118.6(2) . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
F1 C12 C11 119.1(2) . . ?
F1 C12 C13 118.5(3) . . ?
C11 C12 C13 122.4(3) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C7 N1 C1 C2 -176.9(2) . . . . ?
C3 N1 C1 C2 0.9(2) . . . . ?
C7 N1 C1 S1 -4.2(3) . . . . ?
C3 N1 C1 S1 173.61(15) . . . . ?
C15 S1 C1 C2 -107.3(2) . . . . ?
C15 S1 C1 N1 82.2(2) . . . . ?
C3 N2 C2 C1 0.2(2) . . . . ?
C3 N2 C2 C9 -176.84(19) . . . . ?
N1 C1 C2 N2 -0.7(2) . . . . ?
S1 C1 C2 N2 -172.37(17) . . . . ?
N1 C1 C2 C9 176.0(2) . . . . ?
S1 C1 C2 C9 4.3(4) . . . . ?
C2 N2 C3 N1 0.4(2) . . . . ?
C2 N2 C3 C4 -179.7(2) . . . . ?
C7 N1 C3 N2 177.27(19) . . . . ?
C1 N1 C3 N2 -0.8(2) . . . . ?
C7 N1 C3 C4 -2.7(3) . . . . ?
C1 N1 C3 C4 179.24(19) . . . . ?
N2 C3 C4 C5 -177.5(2) . . . . ?
N1 C3 C4 C5 2.5(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 178.5(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C8 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 N1 0.6(4) . . . . ?
C3 N1 C7 C6 1.2(3) . . . . ?
C1 N1 C7 C6 178.8(2) . . . . ?
N2 C2 C9 C14 -142.9(2) . . . . ?
C1 C2 C9 C14 40.7(3) . . . . ?
N2 C2 C9 C10 34.8(3) . . . . ?
C1 C2 C9 C10 -141.6(2) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C2 C9 C10 C11 -178.0(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 F1 179.5(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
F1 C12 C13 C14 -179.8(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 0.3(4) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C2 C9 C14 C13 177.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
