# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 2071615'
loop_
_audit_author_name
_audit_author_address
'Xiaolin Zhu'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-08-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C14 H11 N2 O S'
_chemical_formula_sum            'C15 H11 F3 N2 O4 S2'
_chemical_formula_weight         404.38
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.4424(12)
_cell_length_b                   10.2099(8)
_cell_length_c                   20.8080(15)
_cell_angle_alpha                90
_cell_angle_beta                 110.745(2)
_cell_angle_gamma                90
_cell_volume                     3266.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9470
_cell_measurement_temperature    153.0
_cell_measurement_theta_max      68.209
_cell_measurement_theta_min      4.545
_shelx_estimated_absorpt_T_max   0.419
_shelx_estimated_absorpt_T_min   0.272
_exptl_absorpt_coefficient_mu    3.515
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1238 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.7378.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24564
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.304
_diffrn_reflns_theta_min         4.544
_diffrn_ambient_temperature      153.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_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                2755
_reflns_number_total             2978
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+1.9062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.63253(2) 0.44733(3) 0.40722(2) 0.02332(11) Uani 1 1 d . . . . .
S2 S 0.52849(2) -0.17553(3) 0.46447(2) 0.02366(11) Uani 1 1 d . . . . .
O1 O 0.62534(7) 0.36097(12) 0.45952(5) 0.0321(2) Uani 1 1 d . . . . .
O2 O 0.57344(7) 0.55706(11) 0.39142(6) 0.0310(3) Uani 1 1 d . . . . .
F1 F 0.75525(7) 0.60878(12) 0.40461(6) 0.0506(3) Uani 1 1 d . . . . .
O3 O 0.64174(7) 0.38365(11) 0.34829(5) 0.0327(3) Uani 1 1 d . . . . .
F2 F 0.80254(7) 0.43721(13) 0.46588(6) 0.0538(3) Uani 1 1 d . . . . .
F3 F 0.74285(7) 0.59150(13) 0.50373(6) 0.0516(3) Uani 1 1 d . . . . .
O4 O 0.34605(8) 1.03155(11) 0.21613(6) 0.0364(3) Uani 1 1 d . . . . .
N1 N 0.46666(8) 0.07708(12) 0.41770(6) 0.0227(2) Uani 1 1 d . . . . .
N2 N 0.37489(7) 0.53831(11) 0.33730(6) 0.0211(2) Uani 1 1 d . . . . .
C1 C 0.40985(9) 0.41909(14) 0.44135(7) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.417880 0.417605 0.488859 0.028 Uiso 1 1 calc R U . . .
C2 C 0.38828(9) 0.53382(14) 0.40539(7) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.382598 0.611607 0.428493 0.027 Uiso 1 1 calc R U . . .
C3 C 0.42010(8) 0.30446(14) 0.40880(7) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.40226(9) 0.30959(14) 0.33783(7) 0.0246(3) Uani 1 1 d . . . . .
H4 H 0.405597 0.232315 0.313450 0.030 Uiso 1 1 calc R U . . .
C5 C 0.45076(9) 0.18376(14) 0.44678(7) 0.0217(3) Uani 1 1 d . . . . .
C6 C 0.32007(9) 0.88894(15) 0.29448(8) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.295601 0.960773 0.310327 0.032 Uiso 1 1 calc R U . . .
C7 C 0.36209(9) 0.66317(14) 0.30226(7) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.38001(9) 0.42629(14) 0.30373(7) 0.0241(3) Uani 1 1 d . . . . .
H8 H 0.367899 0.429005 0.255586 0.029 Uiso 1 1 calc R U . . .
C9 C 0.49595(9) -0.01609(14) 0.46674(7) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.35197(10) 0.90740(15) 0.24132(8) 0.0277(3) Uani 1 1 d . . . . .
C11 C 0.32372(9) 0.76759(15) 0.32420(7) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.300276 0.755015 0.359425 0.030 Uiso 1 1 calc R U . . .
C12 C 0.39248(10) 0.68036(15) 0.24862(8) 0.0285(3) Uani 1 1 d . . . . .
H12 H 0.417439 0.608655 0.233112 0.034 Uiso 1 1 calc R U . . .
C13 C 0.38656(11) 0.80187(16) 0.21753(8) 0.0321(3) Uani 1 1 d . . . . .
H13 H 0.406120 0.812910 0.180034 0.039 Uiso 1 1 calc R U . . .
C14 C 0.73872(10) 0.52522(18) 0.44763(9) 0.0345(4) Uani 1 1 d . . . . .
C15 C 0.38196(17) 1.05532(18) 0.16354(11) 0.0504(5) Uani 1 1 d . . . . .
H15A H 0.350240 1.003481 0.122700 0.076 Uiso 1 1 calc R U . . .
H15B H 0.443453 1.030116 0.180406 0.076 Uiso 1 1 calc R U . . .
H15C H 0.376685 1.148586 0.151640 0.076 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 O1 1.4376(11) . ?
S1 O2 1.4425(11) . ?
S1 O3 1.4425(10) . ?
S1 C14 1.8298(17) . ?
S2 C5 1.7572(14) 5_656 ?
S2 C9 1.7194(14) . ?
F1 C14 1.332(2) . ?
F2 C14 1.331(2) . ?
F3 C14 1.3300(19) . ?
O4 C10 1.3618(18) . ?
O4 C15 1.436(2) . ?
N1 C5 1.3164(18) . ?
N1 C9 1.3527(19) . ?
N2 C2 1.3552(18) . ?
N2 C7 1.4466(18) . ?
N2 C8 1.3583(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(2) . ?
C1 C3 1.3920(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4011(19) . ?
C3 C5 1.454(2) . ?
C4 H4 0.9500 . ?
C4 C8 1.369(2) . ?
C6 H6 0.9500 . ?
C6 C10 1.395(2) . ?
C6 C11 1.376(2) . ?
C7 C11 1.395(2) . ?
C7 C12 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C9 1.382(3) 5_656 ?
C10 C13 1.389(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 S1 O2 114.81(6) . . ?
O1 S1 O3 115.37(7) . . ?
O1 S1 C14 103.87(7) . . ?
O2 S1 C14 102.89(8) . . ?
O3 S1 O2 114.92(7) . . ?
O3 S1 C14 102.48(7) . . ?
C9 S2 C5 87.88(7) . 5_656 ?
C10 O4 C15 117.25(13) . . ?
C5 N1 C9 108.11(12) . . ?
C2 N2 C7 119.84(11) . . ?
C2 N2 C8 119.51(12) . . ?
C8 N2 C7 120.47(11) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C3 120.44(13) . . ?
C3 C1 H1 119.8 . . ?
N2 C2 C1 121.04(13) . . ?
N2 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C1 C3 C4 117.72(13) . . ?
C1 C3 C5 121.77(13) . . ?
C4 C3 C5 120.48(13) . . ?
C3 C4 H4 120.1 . . ?
C8 C4 C3 119.79(13) . . ?
C8 C4 H4 120.1 . . ?
N1 C5 S2 116.56(11) . 5_656 ?
N1 C5 C3 122.58(12) . . ?
C3 C5 S2 120.83(10) . 5_656 ?
C10 C6 H6 119.7 . . ?
C11 C6 H6 119.7 . . ?
C11 C6 C10 120.61(13) . . ?
C11 C7 N2 120.68(12) . . ?
C12 C7 N2 119.21(12) . . ?
C12 C7 C11 120.03(13) . . ?
N2 C8 C4 121.35(13) . . ?
N2 C8 H8 119.3 . . ?
C4 C8 H8 119.3 . . ?
N1 C9 S2 132.55(11) . . ?
N1 C9 C9 118.06(16) . 5_656 ?
C9 C9 S2 109.38(14) 5_656 . ?
O4 C10 C6 115.80(13) . . ?
O4 C10 C13 124.57(13) . . ?
C13 C10 C6 119.63(14) . . ?
C6 C11 C7 119.57(13) . . ?
C6 C11 H11 120.2 . . ?
C7 C11 H11 120.2 . . ?
C7 C12 H12 119.9 . . ?
C7 C12 C13 120.22(13) . . ?
C13 C12 H12 119.9 . . ?
C10 C13 H13 120.1 . . ?
C12 C13 C10 119.84(14) . . ?
C12 C13 H13 120.1 . . ?
F1 C14 S1 110.99(12) . . ?
F2 C14 S1 111.43(13) . . ?
F2 C14 F1 107.22(13) . . ?
F3 C14 S1 111.61(10) . . ?
F3 C14 F1 107.74(15) . . ?
F3 C14 F2 107.65(14) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 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
O1 S1 C14 F1 179.58(11) . . . . ?
O1 S1 C14 F2 60.16(12) . . . . ?
O1 S1 C14 F3 -60.23(15) . . . . ?
O2 S1 C14 F1 -60.43(13) . . . . ?
O2 S1 C14 F2 -179.85(11) . . . . ?
O2 S1 C14 F3 59.77(14) . . . . ?
O3 S1 C14 F1 59.13(13) . . . . ?
O3 S1 C14 F2 -60.29(13) . . . . ?
O3 S1 C14 F3 179.33(13) . . . . ?
O4 C10 C13 C12 177.57(15) . . . . ?
N2 C7 C11 C6 173.57(13) . . . . ?
N2 C7 C12 C13 -175.36(14) . . . . ?
C1 C3 C4 C8 3.3(2) . . . . ?
C1 C3 C5 S2 2.99(18) . . . 5_656 ?
C1 C3 C5 N1 -175.10(12) . . . . ?
C2 N2 C7 C11 -30.13(19) . . . . ?
C2 N2 C7 C12 146.56(14) . . . . ?
C2 N2 C8 C4 -3.0(2) . . . . ?
C2 C1 C3 C4 -3.9(2) . . . . ?
C2 C1 C3 C5 174.23(13) . . . . ?
C3 C1 C2 N2 1.2(2) . . . . ?
C3 C4 C8 N2 0.1(2) . . . . ?
C4 C3 C5 S2 -178.89(10) . . . 5_656 ?
C4 C3 C5 N1 3.0(2) . . . . ?
C5 S2 C9 N1 179.53(14) 5_656 . . . ?
C5 S2 C9 C9 0.33(13) 5_656 . . 5_656 ?
C5 N1 C9 S2 -179.83(11) . . . . ?
C5 N1 C9 C9 -0.7(2) . . . 5_656 ?
C5 C3 C4 C8 -174.91(13) . . . . ?
C6 C10 C13 C12 -2.7(2) . . . . ?
C7 N2 C2 C1 -172.86(12) . . . . ?
C7 N2 C8 C4 172.18(13) . . . . ?
C7 C12 C13 C10 1.5(2) . . . . ?
C8 N2 C2 C1 2.3(2) . . . . ?
C8 N2 C7 C11 154.76(13) . . . . ?
C8 N2 C7 C12 -28.55(19) . . . . ?
C9 N1 C5 S2 0.39(15) . . . 5_656 ?
C9 N1 C5 C3 178.57(12) . . . . ?
C10 C6 C11 C7 1.9(2) . . . . ?
C11 C6 C10 O4 -179.30(13) . . . . ?
C11 C6 C10 C13 0.9(2) . . . . ?
C11 C7 C12 C13 1.4(2) . . . . ?
C12 C7 C11 C6 -3.1(2) . . . . ?
C15 O4 C10 C6 177.18(16) . . . . ?
C15 O4 C10 C13 -3.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
