# 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_191108e
_audit_block_doi                 10.5517/ccdc.csd.cc240yx1
_database_code_depnum_ccdc_archive 'CCDC 1967133'
loop_
_audit_author_name
_audit_author_address
'Yan Liu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 F3 N3 S, C2 H7 O S'
_chemical_formula_sum            'C17 H15 F3 N3 O S2'
_chemical_formula_weight         398.44
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1450(6)
_cell_length_b                   10.3161(9)
_cell_length_c                   12.2769(11)
_cell_angle_alpha                101.410(3)
_cell_angle_beta                 103.927(3)
_cell_angle_gamma                93.498(2)
_cell_volume                     855.32(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.508
_cell_measurement_theta_min      2.371
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             410
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4416
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         2.956
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2361
_reflns_number_total             3001
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0896P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1a)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.14643(14) 0.09487(7) -0.10922(7) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.2213(3) 0.3293(2) -0.15639(17) 0.0356(5) Uani 1 1 d . . . . .
H1 H 0.2171 0.2825 -0.2234 0.043 Uiso 1 1 calc R . . . .
N2 N 0.1888(3) 0.31731(19) 0.13481(16) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.2625(4) 0.5499(2) -0.0348(2) 0.0298(6) Uani 1 1 d . . . . .
N3 N 0.2402(3) 0.54190(19) 0.16465(16) 0.0320(5) Uani 1 1 d . . . . .
F2 F 0.1226(3) 0.65502(17) 0.37690(15) 0.0647(6) Uani 1 1 d . . . . .
C2 C 0.2036(4) 0.3465(2) 0.0318(2) 0.0308(6) Uani 1 1 d . . . . .
C3 C 0.2354(4) 0.4841(2) 0.0537(2) 0.0298(6) Uani 1 1 d . . . . .
C4 C 0.2583(4) 0.4660(2) -0.1410(2) 0.0314(6) Uani 1 1 d . . . . .
C5 C 0.3256(4) 0.7406(3) -0.1109(2) 0.0419(7) Uani 1 1 d . . . . .
H5 H 0.3475 0.8324 -0.1020 0.050 Uiso 1 1 calc R . . . .
C6 C 0.1909(4) 0.2612(2) -0.0769(2) 0.0356(6) Uani 1 1 d . . . . .
C7 C 0.2137(4) 0.4401(2) 0.2122(2) 0.0303(6) Uani 1 1 d . . . . .
F3 F 0.4200(3) 0.62933(18) 0.43200(16) 0.0661(6) Uani 1 1 d . . . . .
F1 F 0.2174(4) 0.5548(2) 0.51213(15) 0.0821(7) Uani 1 1 d . . . . .
C8 C 0.2907(4) 0.5210(3) -0.2308(2) 0.0376(6) Uani 1 1 d . . . . .
H8 H 0.2894 0.4661 -0.3010 0.045 Uiso 1 1 calc R . . . .
C9 C 0.1604(4) 0.1986(2) 0.1667(2) 0.0388(6) Uani 1 1 d . . . . .
H9 H 0.1437 0.1183 0.1133 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2095(4) 0.4385(2) 0.3267(2) 0.0340(6) Uani 1 1 d . . . . .
C11 C 0.3244(4) 0.6556(3) -0.2149(2) 0.0413(7) Uani 1 1 d . . . . .
H11 H 0.3472 0.6918 -0.2747 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2943(4) 0.6874(2) -0.0223(2) 0.0360(6) Uani 1 1 d . . . . .
H12 H 0.2942 0.7435 0.0470 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1824(4) 0.3205(3) 0.3576(2) 0.0403(7) Uani 1 1 d . . . . .
H13 H 0.1806 0.3196 0.4330 0.048 Uiso 1 1 calc R . . . .
C14 C 0.1571(4) 0.2001(3) 0.2761(2) 0.0421(7) Uani 1 1 d . . . . .
H14 H 0.1377 0.1201 0.2980 0.051 Uiso 1 1 calc R . . . .
C15 C 0.2410(5) 0.5690(3) 0.4110(2) 0.0432(7) Uani 1 1 d . . . . .
S2 S 0.35515(12) 0.09473(7) -0.41493(6) 0.0466(3) Uani 1 1 d . . . . .
O1 O 0.2180(3) 0.1923(2) -0.38915(18) 0.0535(6) Uani 1 1 d . . . . .
H1A H 0.1107 0.1525 -0.3979 0.080 Uiso 1 1 calc GR . . . .
C16 C 0.5461(5) 0.1182(3) -0.2882(3) 0.0631(9) Uani 1 1 d . . . . .
H16A H 0.6059 0.2085 -0.2683 0.095 Uiso 1 1 calc GR . . . .
H16B H 0.6408 0.0588 -0.3010 0.095 Uiso 1 1 calc GR . . . .
H16C H 0.4951 0.0999 -0.2266 0.095 Uiso 1 1 calc GR . . . .
C17 C 0.2490(6) -0.0648(3) -0.4093(3) 0.0650(10) Uani 1 1 d . . . . .
H17A H 0.2129 -0.0585 -0.3382 0.098 Uiso 1 1 calc GR . . . .
H17B H 0.3414 -0.1281 -0.4142 0.098 Uiso 1 1 calc GR . . . .
H17C H 0.1358 -0.0934 -0.4725 0.098 Uiso 1 1 calc GR . . . .


_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 C6 1.676(3) . ?
N1 H1 0.8600 . ?
N1 C4 1.385(3) . ?
N1 C6 1.359(3) . ?
N2 C2 1.383(3) . ?
N2 C7 1.398(3) . ?
N2 C9 1.375(3) . ?
C1 C3 1.434(3) . ?
C1 C4 1.408(3) . ?
C1 C12 1.394(3) . ?
N3 C3 1.366(3) . ?
N3 C7 1.323(3) . ?
F2 C15 1.321(3) . ?
C2 C3 1.385(3) . ?
C2 C6 1.425(3) . ?
C4 C8 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C11 1.396(4) . ?
C5 C12 1.369(4) . ?
C7 C10 1.417(3) . ?
F3 C15 1.330(4) . ?
F1 C15 1.328(3) . ?
C8 H8 0.9300 . ?
C8 C11 1.362(4) . ?
C9 H9 0.9300 . ?
C9 C14 1.347(4) . ?
C10 C13 1.362(4) . ?
C10 C15 1.494(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.403(4) . ?
C14 H14 0.9300 . ?
S2 O1 1.489(2) . ?
S2 C16 1.769(3) . ?
S2 C17 1.791(3) . ?
O1 H1A 0.8200 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C4 N1 H1 116.5 . . ?
C6 N1 H1 116.5 . . ?
C6 N1 C4 126.9(2) . . ?
C2 N2 C7 105.67(19) . . ?
C9 N2 C2 132.1(2) . . ?
C9 N2 C7 122.2(2) . . ?
C4 C1 C3 115.7(2) . . ?
C12 C1 C3 125.1(2) . . ?
C12 C1 C4 119.2(2) . . ?
C7 N3 C3 104.17(19) . . ?
N2 C2 C3 105.1(2) . . ?
N2 C2 C6 130.8(2) . . ?
C3 C2 C6 124.1(2) . . ?
N3 C3 C1 127.3(2) . . ?
N3 C3 C2 112.3(2) . . ?
C2 C3 C1 120.4(2) . . ?
N1 C4 C1 120.1(2) . . ?
N1 C4 C8 120.1(2) . . ?
C8 C4 C1 119.7(2) . . ?
C11 C5 H5 120.4 . . ?
C12 C5 H5 120.4 . . ?
C12 C5 C11 119.2(2) . . ?
N1 C6 S1 121.23(18) . . ?
N1 C6 C2 112.6(2) . . ?
C2 C6 S1 126.1(2) . . ?
N2 C7 C10 117.3(2) . . ?
N3 C7 N2 112.7(2) . . ?
N3 C7 C10 129.9(2) . . ?
C4 C8 H8 120.3 . . ?
C11 C8 C4 119.5(2) . . ?
C11 C8 H8 120.3 . . ?
N2 C9 H9 120.4 . . ?
C14 C9 N2 119.1(2) . . ?
C14 C9 H9 120.4 . . ?
C7 C10 C15 117.8(2) . . ?
C13 C10 C7 120.0(2) . . ?
C13 C10 C15 122.1(2) . . ?
C5 C11 H11 119.2 . . ?
C8 C11 C5 121.7(2) . . ?
C8 C11 H11 119.2 . . ?
C1 C12 H12 119.6 . . ?
C5 C12 C1 120.7(2) . . ?
C5 C12 H12 119.6 . . ?
C10 C13 H13 119.9 . . ?
C10 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 121.1(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
F2 C15 F3 106.1(2) . . ?
F2 C15 F1 106.5(3) . . ?
F2 C15 C10 113.6(2) . . ?
F3 C15 C10 112.2(2) . . ?
F1 C15 F3 106.0(2) . . ?
F1 C15 C10 111.9(2) . . ?
O1 S2 C16 106.14(15) . . ?
O1 S2 C17 107.00(16) . . ?
C16 S2 C17 97.49(16) . . ?
S2 O1 H1A 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S2 C17 H17A 109.5 . . ?
S2 C17 H17B 109.5 . . ?
S2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
