# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_dr
_audit_block_doi                 10.5517/ccdc.csd.cc2d8llw
_database_code_depnum_ccdc_archive 'CCDC 2212798'
loop_
_audit_author_name
_audit_author_address
'Weiming Chen'
;Gannan Medical University
China
;
_audit_update_record             
;
2022-10-13 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_audit_creation_date             2022-05-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 F3 N6 O2 S'
_chemical_formula_sum            'C16 H15 F3 N6 O2 S'
_chemical_formula_weight         412.40
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.715(6)
_cell_length_b                   7.738(4)
_cell_length_c                   19.834(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.723(10)
_cell_angle_gamma                90
_cell_volume                     1788.9(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4037
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.27
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38273
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.104
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1585
_reflns_number_total             3161
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.056
_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)+(0.0542P)²+0.9059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.17022(9) 0.52068(14) 0.59579(5) 0.0590(4) Uani 1 1 d . . . . .
F1 F 0.2161(2) 0.1076(3) 0.52904(12) 0.0788(8) Uani 1 1 d . . . . .
F2 F 0.6478(2) 0.3476(4) 0.52338(13) 0.0994(10) Uani 1 1 d . . . . .
F3 F 0.5372(2) 0.2100(4) 0.41156(12) 0.1024(10) Uani 1 1 d . . . . .
O1 O 0.4164(2) 0.8779(4) 0.75414(14) 0.0654(8) Uani 1 1 d . . . . .
O2 O 0.4739(2) 0.2988(4) 0.76233(13) 0.0581(8) Uani 1 1 d . . . . .
N1 N 0.2946(3) 0.7088(4) 0.68611(16) 0.0487(8) Uani 1 1 d . . . . .
N2 N 0.4387(3) 0.5877(4) 0.76452(15) 0.0474(8) Uani 1 1 d . . . . .
N3 N 0.3354(3) 0.4095(4) 0.68547(15) 0.0439(8) Uani 1 1 d . . . . .
N4 N 0.6589(3) 0.5939(4) 0.72209(17) 0.0570(9) Uani 1 1 d . . . . .
N5 N 0.7741(3) 0.5697(4) 0.71995(17) 0.0566(9) Uani 1 1 d . . . . .
N6 N 0.7476(3) 0.5611(5) 0.82722(18) 0.0689(11) Uani 1 1 d . . . . .
C1 C 0.3845(3) 0.7346(6) 0.7348(2) 0.0491(10) Uani 1 1 d . . . . .
C2 C 0.2757(3) 0.5552(6) 0.66224(18) 0.0452(10) Uani 1 1 d . . . . .
C3 C 0.4200(3) 0.4235(6) 0.73948(19) 0.0468(10) Uani 1 1 d . . . . .
C4 C 0.5364(3) 0.6077(6) 0.8162(2) 0.0587(12) Uani 1 1 d . . . . .
H4A H 0.531039 0.522062 0.851406 0.070 Uiso 1 1 calc R U . . .
H4B H 0.533180 0.721136 0.836723 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6486(3) 0.5876(5) 0.7872(2) 0.0504(11) Uani 1 1 d . . . . .
C6 C 0.8233(4) 0.5504(6) 0.7820(2) 0.0694(13) Uani 1 1 d . . . . .
H6 H 0.901358 0.531471 0.792790 0.083 Uiso 1 1 calc R U . . .
C7 C 0.8242(4) 0.5680(6) 0.6563(2) 0.0766(14) Uani 1 1 d . . . . .
H7A H 0.790081 0.477133 0.628174 0.115 Uiso 1 1 calc R U . . .
H7B H 0.905331 0.548697 0.664631 0.115 Uiso 1 1 calc R U . . .
H7C H 0.810483 0.677048 0.633890 0.115 Uiso 1 1 calc R U . . .
C8 C 0.3201(3) 0.2405(5) 0.65146(19) 0.0505(10) Uani 1 1 d . . . . .
H8A H 0.238861 0.218189 0.640851 0.061 Uiso 1 1 calc R U . . .
H8B H 0.351271 0.150626 0.682045 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3783(3) 0.2336(5) 0.58751(18) 0.0431(10) Uani 1 1 d . . . . .
C10 C 0.4890(4) 0.2943(5) 0.5850(2) 0.0561(11) Uani 1 1 d . . . . .
H10 H 0.529027 0.341200 0.623515 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5393(4) 0.2855(6) 0.5261(2) 0.0627(12) Uani 1 1 d . . . . .
C12 C 0.4841(5) 0.2175(6) 0.4687(2) 0.0662(13) Uani 1 1 d . . . . .
C13 C 0.3748(4) 0.1548(6) 0.4687(2) 0.0646(13) Uani 1 1 d . . . . .
H13 H 0.335658 0.106831 0.430073 0.078 Uiso 1 1 calc R U . . .
C14 C 0.3261(4) 0.1665(5) 0.5286(2) 0.0533(11) Uani 1 1 d . . . . .
C15 C 0.1283(4) 0.7397(6) 0.5753(2) 0.0735(13) Uani 1 1 d . . . . .
H15A H 0.085262 0.786435 0.610420 0.088 Uiso 1 1 calc R U . . .
H15B H 0.196039 0.810612 0.572765 0.088 Uiso 1 1 calc R U . . .
C16 C 0.0564(5) 0.7435(7) 0.5091(3) 0.112(2) Uani 1 1 d . . . . .
H16A H 0.098019 0.692442 0.474804 0.169 Uiso 1 1 calc R U . . .
H16B H 0.037640 0.861005 0.497005 0.169 Uiso 1 1 calc R U . . .
H16C H -0.012957 0.679453 0.512630 0.169 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 C2 1.735(4) . ?
S1 C15 1.800(4) . ?
F1 C14 1.367(4) . ?
F2 C11 1.364(5) . ?
F3 C12 1.348(5) . ?
O1 C1 1.219(5) . ?
O2 C3 1.216(4) . ?
N1 C1 1.371(5) . ?
N1 C2 1.291(5) . ?
N2 C1 1.403(5) . ?
N2 C3 1.374(5) . ?
N2 C4 1.467(4) . ?
N3 C2 1.382(5) . ?
N3 C3 1.389(5) . ?
N3 C8 1.474(5) . ?
N4 N5 1.368(4) . ?
N4 C5 1.310(5) . ?
N5 C6 1.314(5) . ?
N5 C7 1.444(5) . ?
N6 C5 1.353(5) . ?
N6 C6 1.325(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.494(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.499(5) . ?
C9 C10 1.385(5) . ?
C9 C14 1.365(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(5) . ?
C11 C12 1.357(6) . ?
C12 C13 1.369(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.488(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 S1 C15 100.6(2) . . ?
C2 N1 C1 119.0(3) . . ?
C1 N2 C4 119.8(3) . . ?
C3 N2 C1 123.3(3) . . ?
C3 N2 C4 115.8(3) . . ?
C2 N3 C3 119.5(3) . . ?
C2 N3 C8 122.5(3) . . ?
C3 N3 C8 117.8(3) . . ?
C5 N4 N5 102.3(3) . . ?
N4 N5 C7 121.1(3) . . ?
C6 N5 N4 109.2(3) . . ?
C6 N5 C7 129.7(4) . . ?
C6 N6 C5 101.8(3) . . ?
O1 C1 N1 122.9(4) . . ?
O1 C1 N2 119.6(4) . . ?
N1 C1 N2 117.5(4) . . ?
N1 C2 S1 120.2(3) . . ?
N1 C2 N3 124.5(3) . . ?
N3 C2 S1 115.2(3) . . ?
O2 C3 N2 122.8(4) . . ?
O2 C3 N3 122.0(4) . . ?
N2 C3 N3 115.2(4) . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
N2 C4 C5 112.1(3) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N4 C5 N6 115.2(4) . . ?
N4 C5 C4 123.0(4) . . ?
N6 C5 C4 121.7(4) . . ?
N5 C6 N6 111.5(4) . . ?
N5 C6 H6 124.3 . . ?
N6 C6 H6 124.3 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
N3 C8 C9 112.0(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 121.7(4) . . ?
C14 C9 C8 122.3(4) . . ?
C14 C9 C10 116.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 F2 120.0(4) . . ?
C12 C11 F2 118.2(4) . . ?
C12 C11 C10 121.8(4) . . ?
F3 C12 C11 120.0(5) . . ?
F3 C12 C13 119.6(5) . . ?
C11 C12 C13 120.4(4) . . ?
C12 C13 H13 121.8 . . ?
C12 C13 C14 116.5(4) . . ?
C14 C13 H13 121.8 . . ?
F1 C14 C13 117.2(4) . . ?
C9 C14 F1 117.6(4) . . ?
C9 C14 C13 125.2(4) . . ?
S1 C15 H15A 109.7 . . ?
S1 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 S1 109.6(3) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
F2 C11 C12 F3 1.1(6) . . . . ?
F2 C11 C12 C13 -179.5(4) . . . . ?
F3 C12 C13 C14 179.9(4) . . . . ?
N2 C4 C5 N4 15.5(6) . . . . ?
N2 C4 C5 N6 -164.4(4) . . . . ?
N3 C8 C9 C10 45.6(5) . . . . ?
N3 C8 C9 C14 -134.8(4) . . . . ?
N4 N5 C6 N6 -0.4(5) . . . . ?
N5 N4 C5 N6 -0.1(4) . . . . ?
N5 N4 C5 C4 180.0(3) . . . . ?
C1 N1 C2 S1 -174.7(3) . . . . ?
C1 N1 C2 N3 4.6(5) . . . . ?
C1 N2 C3 O2 174.0(3) . . . . ?
C1 N2 C3 N3 -5.4(5) . . . . ?
C1 N2 C4 C5 -98.2(4) . . . . ?
C2 S1 C15 C16 167.3(4) . . . . ?
C2 N1 C1 O1 171.1(3) . . . . ?
C2 N1 C1 N2 -10.9(5) . . . . ?
C2 N3 C3 O2 179.1(3) . . . . ?
C2 N3 C3 N2 -1.5(5) . . . . ?
C2 N3 C8 C9 75.5(4) . . . . ?
C3 N2 C1 O1 -170.2(3) . . . . ?
C3 N2 C1 N1 11.8(5) . . . . ?
C3 N2 C4 C5 70.0(4) . . . . ?
C3 N3 C2 S1 -178.7(2) . . . . ?
C3 N3 C2 N1 2.0(5) . . . . ?
C3 N3 C8 C9 -99.2(4) . . . . ?
C4 N2 C1 O1 -2.9(5) . . . . ?
C4 N2 C1 N1 179.1(3) . . . . ?
C4 N2 C3 O2 6.3(5) . . . . ?
C4 N2 C3 N3 -173.2(3) . . . . ?
C5 N4 N5 C6 0.3(4) . . . . ?
C5 N4 N5 C7 -179.8(4) . . . . ?
C5 N6 C6 N5 0.3(5) . . . . ?
C6 N6 C5 N4 -0.1(5) . . . . ?
C6 N6 C5 C4 179.8(4) . . . . ?
C7 N5 C6 N6 179.7(4) . . . . ?
C8 N3 C2 S1 6.7(4) . . . . ?
C8 N3 C2 N1 -172.6(3) . . . . ?
C8 N3 C3 O2 -6.1(5) . . . . ?
C8 N3 C3 N2 173.3(3) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
C8 C9 C14 F1 1.3(5) . . . . ?
C8 C9 C14 C13 -179.4(4) . . . . ?
C9 C10 C11 F2 179.1(4) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C9 C14 F1 -179.1(3) . . . . ?
C10 C9 C14 C13 0.3(6) . . . . ?
C10 C11 C12 F3 -179.5(4) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C13 C14 F1 178.7(4) . . . . ?
C12 C13 C14 C9 -0.6(6) . . . . ?
C14 C9 C10 C11 0.2(6) . . . . ?
C15 S1 C2 N1 6.1(4) . . . . ?
C15 S1 C2 N3 -173.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
