# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2060107'
loop_
_audit_author_name
_audit_author_address
'Alexander Goloveshkin'
;Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;
_audit_creation_date             2021-02-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H18 F N3 O3 S'
_chemical_formula_sum            'C21 H18 F N3 O3 S'
_chemical_formula_weight         411.44
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.3130(3)
_cell_length_b                   10.5521(4)
_cell_length_c                   11.4329(4)
_cell_angle_alpha                109.117(2)
_cell_angle_beta                 92.400(2)
_cell_angle_gamma                94.583(2)
_cell_volume                     942.08(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4631
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      3.00
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9414
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11451
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.89
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_number_gt                4368
_reflns_number_total             5552
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5552
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0903P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1624
_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. 
;
_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. Restrained distances
 N1-H1 = N3-H3
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C8(H8), C2(H2), C12(H12), C20(H20), C19(H19), C13(H13),
 C5(H5), C10(H10), C11(H11), C4(H4), C3(H3A)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.28320(4) 0.84526(4) 0.61814(3) 0.03391(13) Uani 1 1 d . . .
F1 F 0.09033(14) 0.97831(11) 1.30814(9) 0.0530(3) Uani 1 1 d . . .
N1 N 0.28847(16) 0.96344(13) 0.75278(12) 0.0360(3) Uani 1 1 d D . .
O2 O 0.13675(13) 0.76225(13) 0.61100(11) 0.0454(3) Uani 1 1 d . . .
O3 O 0.30995(15) 0.90498(13) 0.52447(11) 0.0457(3) Uani 1 1 d . . .
C14 C 0.39852(17) 1.07952(14) 0.80093(14) 0.0317(3) Uani 1 1 d . . .
N3 N 0.16154(18) 0.95182(15) 1.07450(13) 0.0422(3) Uani 1 1 d D . .
C15 C 0.44565(17) 0.75164(15) 0.62688(13) 0.0328(3) Uani 1 1 d . . .
N2 N 0.23324(18) 0.99212(15) 0.98558(12) 0.0399(3) Uani 1 1 d . . .
C6 C -0.00180(19) 0.78475(15) 1.13638(14) 0.0352(3) Uani 1 1 d . . .
C16 C 0.60099(19) 0.79387(16) 0.60532(15) 0.0378(3) Uani 1 1 d . . .
H16 H 0.6192 0.8693 0.5808 0.045 Uiso 1 1 calc R . .
C17 C 0.72775(19) 0.72268(16) 0.62072(16) 0.0399(3) Uani 1 1 d . . .
H17 H 0.8320 0.7522 0.6082 0.048 Uiso 1 1 calc R . .
C1 C 0.00813(19) 0.85403(15) 1.26282(14) 0.0358(3) Uani 1 1 d . . .
C8 C 0.3263(2) 1.10034(18) 1.01887(15) 0.0428(4) Uani 1 1 d . . .
H8 H 0.3411 1.1510 1.1028 0.051 Uiso 1 1 calc R . .
C9 C 0.41119(19) 1.14832(16) 0.93019(14) 0.0362(3) Uani 1 1 d . . .
C7 C 0.0713(2) 0.83059(17) 1.03761(15) 0.0409(4) Uani 1 1 d . . .
C2 C -0.0619(2) 0.80387(18) 1.34709(15) 0.0433(4) Uani 1 1 d . . .
H2 H -0.0531 0.8540 1.4312 0.052 Uiso 1 1 calc R . .
C12 C 0.5920(2) 1.24957(18) 0.77566(18) 0.0447(4) Uani 1 1 d . . .
H12 H 0.6545 1.2821 0.7240 0.054 Uiso 1 1 calc R . .
C20 C 0.4181(2) 0.63768(17) 0.66143(16) 0.0418(4) Uani 1 1 d . . .
H20 H 0.3142 0.6096 0.6761 0.050 Uiso 1 1 calc R . .
C19 C 0.5461(2) 0.56662(18) 0.67373(18) 0.0463(4) Uani 1 1 d . . .
H19 H 0.5273 0.4894 0.6954 0.056 Uiso 1 1 calc R . .
C13 C 0.4912(2) 1.13172(17) 0.72514(15) 0.0397(3) Uani 1 1 d . . .
H13 H 0.4850 1.0868 0.6400 0.048 Uiso 1 1 calc R . .
C5 C -0.0876(2) 0.65723(18) 1.09746(17) 0.0479(4) Uani 1 1 d . . .
H5 H -0.0980 0.6070 1.0133 0.058 Uiso 1 1 calc R . .
C18 C 0.7032(2) 0.60801(16) 0.65444(15) 0.0396(3) Uani 1 1 d . . .
O1 O 0.0504(2) 0.76171(16) 0.92942(12) 0.0695(5) Uani 1 1 d . . .
C10 C 0.5126(2) 1.26857(19) 0.97639(17) 0.0506(4) Uani 1 1 d . . .
H10 H 0.5201 1.3157 1.0612 0.061 Uiso 1 1 calc R . .
C21 C 0.8429(2) 0.5316(2) 0.6702(2) 0.0558(5) Uani 1 1 d . . .
H21A H 0.8561 0.4626 0.5930 0.084 Uiso 1 1 calc R . .
H21B H 0.8220 0.4910 0.7326 0.084 Uiso 1 1 calc R . .
H21C H 0.9400 0.5924 0.6952 0.084 Uiso 1 1 calc R . .
C11 C 0.6018(2) 1.31924(19) 0.89971(19) 0.0525(5) Uani 1 1 d . . .
H11 H 0.6678 1.3999 0.9323 0.063 Uiso 1 1 calc R . .
C4 C -0.1571(3) 0.6039(2) 1.18006(19) 0.0555(5) Uani 1 1 d . . .
H4 H -0.2119 0.5179 1.1519 0.067 Uiso 1 1 calc R . .
C3 C -0.1456(2) 0.6774(2) 1.30417(18) 0.0503(4) Uani 1 1 d . . .
H3A H -0.1946 0.6417 1.3597 0.060 Uiso 1 1 calc R . .
H1 H 0.244(2) 0.938(2) 0.8074(17) 0.047(5) Uiso 1 1 d D . .
H3 H 0.180(3) 1.008(2) 1.1485(16) 0.070(7) Uiso 1 1 d D . .


_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 N1 1.6294(13) . ?
S1 O2 1.4250(12) . ?
S1 O3 1.4258(12) . ?
S1 C15 1.7539(16) . ?
F1 C1 1.3554(18) . ?
N1 C14 1.4062(19) . ?
N1 H1 0.844(15) . ?
C14 C9 1.412(2) . ?
C14 C13 1.396(2) . ?
N3 N2 1.3650(18) . ?
N3 C7 1.358(2) . ?
N3 H3 0.860(16) . ?
C15 C16 1.390(2) . ?
C15 C20 1.389(2) . ?
N2 C8 1.264(2) . ?
C6 C1 1.385(2) . ?
C6 C7 1.499(2) . ?
C6 C5 1.395(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C1 C2 1.371(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.456(2) . ?
C9 C10 1.397(2) . ?
C7 O1 1.209(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C12 C11 1.363(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.378(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.393(2) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.373(3) . ?
C18 C21 1.503(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.371(3) . ?
C3 H3A 0.9300 . ?

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
N1 S1 C15 105.84(7) . . ?
O2 S1 N1 104.80(7) . . ?
O2 S1 O3 119.57(8) . . ?
O2 S1 C15 108.10(8) . . ?
O3 S1 N1 109.35(7) . . ?
O3 S1 C15 108.35(7) . . ?
S1 N1 H1 113.7(14) . . ?
C14 N1 S1 128.21(11) . . ?
C14 N1 H1 114.1(14) . . ?
N1 C14 C9 118.68(13) . . ?
C13 C14 N1 122.36(14) . . ?
C13 C14 C9 118.92(14) . . ?
N2 N3 H3 114.2(16) . . ?
C7 N3 N2 117.80(13) . . ?
C7 N3 H3 128.0(16) . . ?
C16 C15 S1 120.75(12) . . ?
C20 C15 S1 118.84(11) . . ?
C20 C15 C16 120.34(15) . . ?
C8 N2 N3 118.75(14) . . ?
C1 C6 C7 127.32(14) . . ?
C1 C6 C5 116.01(15) . . ?
C5 C6 C7 116.67(14) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.26(15) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.51(14) . . ?
C18 C17 H17 119.2 . . ?
F1 C1 C6 119.61(14) . . ?
F1 C1 C2 116.93(14) . . ?
C2 C1 C6 123.46(15) . . ?
N2 C8 H8 118.9 . . ?
N2 C8 C9 122.18(15) . . ?
C9 C8 H8 118.9 . . ?
C14 C9 C8 123.82(14) . . ?
C10 C9 C14 118.34(15) . . ?
C10 C9 C8 117.83(15) . . ?
N3 C7 C6 117.45(14) . . ?
O1 C7 N3 121.59(15) . . ?
O1 C7 C6 120.96(15) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.42(16) . . ?
C3 C2 H2 120.8 . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.26(16) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.32(15) . . ?
C19 C20 H20 120.3 . . ?
C20 C19 H19 119.3 . . ?
C20 C19 C18 121.42(16) . . ?
C18 C19 H19 119.3 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.48(15) . . ?
C12 C13 H13 119.8 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.73(16) . . ?
C4 C5 H5 119.1 . . ?
C17 C18 C19 118.12(15) . . ?
C17 C18 C21 120.66(15) . . ?
C19 C18 C21 121.21(16) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.81(16) . . ?
C11 C10 H10 119.1 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C11 C10 119.14(16) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.96(17) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 C2 120.42(17) . . ?
C4 C3 H3A 119.8 . . ?

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
S1 N1 C14 C9 -162.14(12) . . . . ?
S1 N1 C14 C13 20.2(2) . . . . ?
S1 C15 C16 C17 175.87(12) . . . . ?
S1 C15 C20 C19 -177.26(13) . . . . ?
F1 C1 C2 C3 -179.63(16) . . . . ?
N1 S1 C15 C16 -83.50(13) . . . . ?
N1 S1 C15 C20 93.53(14) . . . . ?
N1 C14 C9 C8 5.2(2) . . . . ?
N1 C14 C9 C10 -175.72(16) . . . . ?
N1 C14 C13 C12 176.84(15) . . . . ?
O2 S1 N1 C14 -172.69(14) . . . . ?
O2 S1 C15 C16 164.65(12) . . . . ?
O2 S1 C15 C20 -18.32(15) . . . . ?
O3 S1 N1 C14 -43.35(16) . . . . ?
O3 S1 C15 C16 33.69(14) . . . . ?
O3 S1 C15 C20 -149.27(13) . . . . ?
C14 C9 C10 C11 -1.3(3) . . . . ?
N3 N2 C8 C9 178.16(15) . . . . ?
C15 S1 N1 C14 73.17(15) . . . . ?
C15 C16 C17 C18 1.5(2) . . . . ?
C15 C20 C19 C18 1.2(3) . . . . ?
N2 N3 C7 C6 177.72(14) . . . . ?
N2 N3 C7 O1 -2.2(3) . . . . ?
N2 C8 C9 C14 -0.3(3) . . . . ?
N2 C8 C9 C10 -179.42(18) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C5 C4 C3 1.2(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C16 C17 C18 C21 179.76(16) . . . . ?
C1 C6 C7 N3 2.0(3) . . . . ?
C1 C6 C7 O1 -178.16(18) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C8 C9 C10 C11 177.82(19) . . . . ?
C9 C14 C13 C12 -0.8(2) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C7 N3 N2 C8 -175.39(16) . . . . ?
C7 C6 C1 F1 0.6(3) . . . . ?
C7 C6 C1 C2 -179.54(16) . . . . ?
C7 C6 C5 C4 178.78(18) . . . . ?
C20 C15 C16 C17 -1.1(2) . . . . ?
C20 C19 C18 C17 -0.8(3) . . . . ?
C20 C19 C18 C21 178.87(17) . . . . ?
C13 C14 C9 C8 -177.09(15) . . . . ?
C13 C14 C9 C10 2.0(2) . . . . ?
C13 C12 C11 C10 1.9(3) . . . . ?
C5 C6 C1 F1 179.58(16) . . . . ?
C5 C6 C1 C2 -0.6(3) . . . . ?
C5 C6 C7 N3 -177.00(16) . . . . ?
C5 C6 C7 O1 2.9(3) . . . . ?
C5 C4 C3 C2 -1.3(3) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
