# 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_gg
_audit_block_doi                 10.5517/ccdc.csd.cc2bmw3z
_database_code_depnum_ccdc_archive 'CCDC 2164051'
loop_
_audit_author_name
_audit_author_address
'Yunfei Tian'
;Luoyang Normal University
China
;
_audit_update_record             
;
2022-04-02 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2021-09-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 F3 N2 O S'
_chemical_formula_sum            'C19 H13 F3 N2 O S'
_chemical_formula_weight         374.37
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.5655(3)
_cell_length_b                   25.6875(12)
_cell_length_c                   7.7171(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.0140(10)
_cell_angle_gamma                90
_cell_volume                     1676.99(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9164.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12830
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         2.408
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2300
_reflns_number_total             3436
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.046
_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)+(0.0328P)²+1.0933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1122
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00M(H00M), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00C,H00F,H00K)
;
_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
S01 S 0.13179(9) 0.55355(3) 0.50083(9) 0.0334(2) Uani 1 1 d . . . . .
F002 F 0.7321(2) 0.59243(7) 0.4542(2) 0.0518(5) Uani 1 1 d . . . . .
F003 F 0.5389(2) 0.56426(7) 0.5717(2) 0.0554(5) Uani 1 1 d . . . . .
F004 F 0.7696(2) 0.57142(7) 0.7258(2) 0.0532(5) Uani 1 1 d . . . . .
O005 O 0.6885(2) 0.68533(8) 0.5654(2) 0.0407(5) Uani 1 1 d . . . . .
N006 N 0.5504(2) 0.65863(8) 0.7777(3) 0.0254(5) Uani 1 1 d . . . . .
N007 N -0.0558(3) 0.55029(9) 0.1640(3) 0.0376(6) Uani 1 1 d . . . . .
C008 C 0.2245(3) 0.64497(10) 0.6702(3) 0.0228(6) Uani 1 1 d . . . . .
C009 C 0.4738(3) 0.61918(9) 0.8667(3) 0.0232(6) Uani 1 1 d . . . . .
C00A C 0.3109(3) 0.61297(10) 0.8161(3) 0.0224(6) Uani 1 1 d . . . . .
C00B C 0.3583(3) 0.73307(10) 0.7449(3) 0.0229(6) Uani 1 1 d . . . . .
C00C C 0.2250(3) 0.70303(10) 0.6788(3) 0.0226(6) Uani 1 1 d . . . . .
C00D C 0.2333(3) 0.57622(10) 0.9043(3) 0.0260(6) Uani 1 1 d . . . . .
H00D H 0.123103 0.570689 0.870345 0.031 Uiso 1 1 calc R U . . .
C00E C 0.3467(3) 0.78702(10) 0.7375(3) 0.0258(6) Uani 1 1 d . . . . .
H00E H 0.436655 0.807407 0.781896 0.031 Uiso 1 1 calc R U . . .
C00F C 0.0740(3) 0.78307(10) 0.6049(3) 0.0289(6) Uani 1 1 d . . . . .
C00G C 0.0846(3) 0.72923(10) 0.6133(3) 0.0272(6) Uani 1 1 d . . . . .
H00G H -0.007281 0.709252 0.572925 0.033 Uiso 1 1 calc R U . . .
C00H C 0.2078(3) 0.81187(11) 0.6671(3) 0.0286(6) Uani 1 1 d . . . . .
H00H H 0.204149 0.848807 0.661435 0.034 Uiso 1 1 calc R U . . .
C00I C 0.5558(3) 0.59167(10) 1.0058(3) 0.0289(6) Uani 1 1 d . . . . .
H00I H 0.665671 0.597415 1.041377 0.035 Uiso 1 1 calc R U . . .
C00J C 0.1410(3) 0.62198(9) 0.5296(3) 0.0253(6) Uani 1 1 d . . . . .
H00J H 0.084075 0.643383 0.441093 0.030 Uiso 1 1 calc R U . . .
C00K C 0.6338(3) 0.65073(11) 0.6466(3) 0.0288(6) Uani 1 1 d . . . . .
C00L C 0.5182(3) 0.71202(10) 0.8270(3) 0.0274(6) Uani 1 1 d . . . . .
H00A H 0.601283 0.734979 0.793326 0.033 Uiso 1 1 calc R U . . .
H00B H 0.525788 0.713718 0.956182 0.033 Uiso 1 1 calc R U . . .
C00M C 0.3156(3) 0.54767(10) 1.0413(3) 0.0292(6) Uani 1 1 d . . . . .
H00M H 0.261519 0.522534 1.100008 0.035 Uiso 1 1 calc R U . . .
C00N C 0.0205(3) 0.55239(10) 0.2993(3) 0.0272(6) Uani 1 1 d . . . . .
C00O C 0.4757(3) 0.55545(11) 1.0932(3) 0.0314(6) Uani 1 1 d . . . . .
H00O H 0.530981 0.536108 1.188397 0.038 Uiso 1 1 calc R U . . .
C00P C 0.6673(3) 0.59389(12) 0.5992(4) 0.0357(7) Uani 1 1 d . . . . .
C00Q C -0.0793(3) 0.80915(12) 0.5298(4) 0.0443(8) Uani 1 1 d . . . . .
H00C H -0.118293 0.794579 0.413713 0.066 Uiso 1 1 calc R U . . .
H00F H -0.061762 0.846638 0.519125 0.066 Uiso 1 1 calc R U . . .
H00K H -0.157565 0.803206 0.607697 0.066 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
S01 C00J 1.772(3) . ?
S01 C00N 1.693(3) . ?
F002 C00P 1.325(3) . ?
F003 C00P 1.327(3) . ?
F004 C00P 1.337(3) . ?
O005 C00K 1.222(3) . ?
N006 C009 1.439(3) . ?
N006 C00K 1.343(3) . ?
N006 C00L 1.461(3) . ?
N007 C00N 1.143(3) . ?
C008 C00A 1.493(3) . ?
C008 C00C 1.493(4) . ?
C008 C00J 1.339(3) . ?
C009 C00A 1.398(3) . ?
C009 C00I 1.381(3) . ?
C00A C00D 1.392(3) . ?
C00B C00C 1.406(3) . ?
C00B C00E 1.390(4) . ?
C00B C00L 1.515(3) . ?
C00C C00G 1.402(3) . ?
C00D H00D 0.9500 . ?
C00D C00M 1.385(3) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.384(3) . ?
C00F C00G 1.387(4) . ?
C00F C00H 1.385(4) . ?
C00F C00Q 1.507(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00O 1.391(4) . ?
C00J H00J 0.9500 . ?
C00K C00P 1.543(4) . ?
C00L H00A 0.9900 . ?
C00L H00B 0.9900 . ?
C00M H00M 0.9500 . ?
C00M C00O 1.381(4) . ?
C00O H00O 0.9500 . ?
C00Q H00C 0.9800 . ?
C00Q H00F 0.9800 . ?
C00Q H00K 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
C00N S01 C00J 98.07(12) . . ?
C009 N006 C00L 114.7(2) . . ?
C00K N006 C009 126.1(2) . . ?
C00K N006 C00L 118.9(2) . . ?
C00C C008 C00A 121.3(2) . . ?
C00J C008 C00A 120.4(2) . . ?
C00J C008 C00C 118.3(2) . . ?
C00A C009 N006 117.2(2) . . ?
C00I C009 N006 121.1(2) . . ?
C00I C009 C00A 121.5(2) . . ?
C009 C00A C008 120.2(2) . . ?
C00D C00A C008 121.6(2) . . ?
C00D C00A C009 118.2(2) . . ?
C00C C00B C00L 125.8(2) . . ?
C00E C00B C00C 118.9(2) . . ?
C00E C00B C00L 115.3(2) . . ?
C00B C00C C008 124.1(2) . . ?
C00G C00C C008 117.8(2) . . ?
C00G C00C C00B 118.0(2) . . ?
C00A C00D H00D 119.8 . . ?
C00M C00D C00A 120.5(2) . . ?
C00M C00D H00D 119.8 . . ?
C00B C00E H00E 119.1 . . ?
C00H C00E C00B 121.8(2) . . ?
C00H C00E H00E 119.1 . . ?
C00G C00F C00Q 120.5(2) . . ?
C00H C00F C00G 118.2(2) . . ?
C00H C00F C00Q 121.3(2) . . ?
C00C C00G H00G 118.6 . . ?
C00F C00G C00C 122.8(2) . . ?
C00F C00G H00G 118.6 . . ?
C00E C00H C00F 120.2(2) . . ?
C00E C00H H00H 119.9 . . ?
C00F C00H H00H 119.9 . . ?
C009 C00I H00I 120.3 . . ?
C009 C00I C00O 119.3(2) . . ?
C00O C00I H00I 120.3 . . ?
S01 C00J H00J 118.4 . . ?
C008 C00J S01 123.1(2) . . ?
C008 C00J H00J 118.4 . . ?
O005 C00K N006 124.6(3) . . ?
O005 C00K C00P 117.8(2) . . ?
N006 C00K C00P 117.5(2) . . ?
N006 C00L C00B 114.9(2) . . ?
N006 C00L H00A 108.5 . . ?
N006 C00L H00B 108.5 . . ?
C00B C00L H00A 108.5 . . ?
C00B C00L H00B 108.5 . . ?
H00A C00L H00B 107.5 . . ?
C00D C00M H00M 119.7 . . ?
C00O C00M C00D 120.5(2) . . ?
C00O C00M H00M 119.7 . . ?
N007 C00N S01 178.2(3) . . ?
C00I C00O H00O 120.0 . . ?
C00M C00O C00I 119.9(2) . . ?
C00M C00O H00O 120.0 . . ?
F002 C00P F003 107.2(2) . . ?
F002 C00P F004 106.9(2) . . ?
F002 C00P C00K 110.2(2) . . ?
F003 C00P F004 107.6(2) . . ?
F003 C00P C00K 113.6(2) . . ?
F004 C00P C00K 111.1(2) . . ?
C00F C00Q H00C 109.5 . . ?
C00F C00Q H00F 109.5 . . ?
C00F C00Q H00K 109.5 . . ?
H00C C00Q H00F 109.5 . . ?
H00C C00Q H00K 109.5 . . ?
H00F C00Q H00K 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
O005 C00K C00P F002 -9.9(3) . . . . ?
O005 C00K C00P F003 -130.2(3) . . . . ?
O005 C00K C00P F004 108.4(3) . . . . ?
N006 C009 C00A C008 2.5(3) . . . . ?
N006 C009 C00A C00D -177.9(2) . . . . ?
N006 C009 C00I C00O 177.2(2) . . . . ?
N006 C00K C00P F002 172.0(2) . . . . ?
N006 C00K C00P F003 51.7(3) . . . . ?
N006 C00K C00P F004 -69.7(3) . . . . ?
C008 C00A C00D C00M -178.8(2) . . . . ?
C008 C00C C00G C00F -176.1(2) . . . . ?
C009 N006 C00K O005 174.8(2) . . . . ?
C009 N006 C00K C00P -7.3(3) . . . . ?
C009 N006 C00L C00B -77.7(3) . . . . ?
C009 C00A C00D C00M 1.5(4) . . . . ?
C009 C00I C00O C00M -0.5(4) . . . . ?
C00A C008 C00C C00B 40.1(4) . . . . ?
C00A C008 C00C C00G -141.3(2) . . . . ?
C00A C008 C00J S01 -2.3(4) . . . . ?
C00A C009 C00I C00O 2.6(4) . . . . ?
C00A C00D C00M C00O 0.4(4) . . . . ?
C00B C00C C00G C00F 2.6(4) . . . . ?
C00B C00E C00H C00F 1.4(4) . . . . ?
C00C C008 C00A C009 -58.7(3) . . . . ?
C00C C008 C00A C00D 121.7(3) . . . . ?
C00C C008 C00J S01 179.19(18) . . . . ?
C00C C00B C00E C00H 0.1(4) . . . . ?
C00C C00B C00L N006 22.3(4) . . . . ?
C00D C00M C00O C00I -1.0(4) . . . . ?
C00E C00B C00C C008 176.6(2) . . . . ?
C00E C00B C00C C00G -2.0(3) . . . . ?
C00E C00B C00L N006 -158.0(2) . . . . ?
C00G C00F C00H C00E -0.8(4) . . . . ?
C00H C00F C00G C00C -1.2(4) . . . . ?
C00I C009 C00A C008 177.3(2) . . . . ?
C00I C009 C00A C00D -3.1(4) . . . . ?
C00J C008 C00A C009 122.9(3) . . . . ?
C00J C008 C00A C00D -56.8(3) . . . . ?
C00J C008 C00C C00B -141.5(3) . . . . ?
C00J C008 C00C C00G 37.2(3) . . . . ?
C00K N006 C009 C00A -100.3(3) . . . . ?
C00K N006 C009 C00I 84.8(3) . . . . ?
C00K N006 C00L C00B 96.4(3) . . . . ?
C00L N006 C009 C00A 73.3(3) . . . . ?
C00L N006 C009 C00I -101.6(3) . . . . ?
C00L N006 C00K O005 1.4(4) . . . . ?
C00L N006 C00K C00P 179.4(2) . . . . ?
C00L C00B C00C C008 -3.8(4) . . . . ?
C00L C00B C00C C00G 177.6(2) . . . . ?
C00L C00B C00E C00H -179.6(2) . . . . ?
C00N S01 C00J C008 -176.9(2) . . . . ?
C00Q C00F C00G C00C 178.8(2) . . . . ?
C00Q C00F C00H C00E 179.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
