# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_exp_133
_audit_block_doi                 10.5517/ccdc.csd.cc2mcvhc
_database_code_depnum_ccdc_archive 'CCDC 2424463'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_audit_creation_date             2025-02-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 F2 N2 S3'
_chemical_formula_sum            'C14 H6 F2 N2 S3'
_chemical_formula_weight         336.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H6N2S3F2
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'
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                   15.7783(9)
_cell_length_b                   4.7778(2)
_cell_length_c                   17.6686(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.731(5)
_cell_angle_gamma                90
_cell_volume                     1288.18(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      29.1590
_cell_measurement_theta_min      2.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.0174
-2 0 -1 0.0768
-2 -2 1 0.2964
1 2 -2 0.3190
-1 0 -2 0.0941
1 0 2 0.0078
1 0 -2 0.0794
-1 0 2 0.0233

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'in soln'
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.094
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0000 -0.0000 1.0000 -0.0190 -0.1072 0.0219
-2.0000 0.0000 -1.0000 0.0190 0.1072 -0.0219
-2.0000 -2.0000 1.0000 0.0132 0.1209 0.2860
1.0000 2.0000 -2.0000 -0.0178 -0.0535 -0.3035
-1.0000 0.0000 -2.0000 -0.0327 0.0951 -0.0304
1.0000 -0.0000 2.0000 0.0327 -0.0951 0.0304
1.0000 0.0000 -2.0000 -0.0799 0.0155 -0.0214
-1.0000 -0.0000 2.0000 0.0799 -0.0155 0.0214

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7436
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  95.00   0.50   28.20    --   12.72  24.00  34.00  272
  2  ω     61.00  87.00   0.50   28.20    --   12.72 178.00-180.00   52
  3  ω    -71.00 -24.00   0.50   28.20    --   12.72 -24.00-130.00   94
  4  ω    -17.00  26.00   0.50   28.20    --  -13.34 -99.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0235983000
_diffrn_orient_matrix_UB_12      0.0310746000
_diffrn_orient_matrix_UB_13      0.0281607000
_diffrn_orient_matrix_UB_21      -0.0397800000
_diffrn_orient_matrix_UB_22      -0.0344848000
_diffrn_orient_matrix_UB_23      -0.0276409000
_diffrn_orient_matrix_UB_31      0.0044956000
_diffrn_orient_matrix_UB_32      -0.1410225000
_diffrn_orient_matrix_UB_33      0.0129540000
_diffrn_oxdiff_digest_frames     
;
015d7f2f696443f24f6c0588f808b853e0005046115
;
_diffrn_oxdiff_digest_hkl        
;
01f715e01c6b3950beeafd9337b3f9ca845bd6
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          -
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             2612
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.459
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.084
_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     224
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.052
_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)+(0.0778P)²+1.6641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          -
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S003-C00G \\sim S0-C00G
 with sigma of 0.02
 S003-C00I \\sim S0-C2
 with sigma of 0.02
 C006-C00G \\sim C0-C00G
 with sigma of 0.02
 C006-C00J \\sim C0-C1
 with sigma of 0.02
 C00I-C00J \\sim C2-C1
 with sigma of 0.02
 S003-C00J \\sim S0-C1
 with sigma of 0.04
 C006-C00I \\sim C0-C2
 with sigma of 0.04
 C00G-C00I \\sim C00G-C2
 with sigma of 0.04
 C00G-C00J \\sim C00G-C1
 with sigma of 0.04
 S002-C00H \\sim S1-C00H
 with sigma of 0.02
 S002-C00L \\sim S1-C00M
 with sigma of 0.02
 C009-C00H \\sim C3-C00H
 with sigma of 0.02
 C009-C00K \\sim C3-C4
 with sigma of 0.02
 C00K-C00L \\sim C4-C00M
 with sigma of 0.02
 S002-C00K \\sim S1-C4
 with sigma of 0.04
 C009-C00L \\sim C3-C00M
 with sigma of 0.04
 C00H-C00K \\sim C00H-C4
 with sigma of 0.04
 C00H-C00L \\sim C00H-C00M
 with sigma of 0.04
3. Others
 Sof(S0)=Sof(C0)=Sof(H0)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=1-FVAR(1)
 Sof(S003)=Sof(C006)=Sof(H006)=Sof(C00I)=Sof(H00I)=Sof(C00J)=Sof(H00J)=FVAR(1)
 Sof(C3)=Sof(H3)=Sof(S1)=Sof(C00M)=Sof(H00M)=Sof(C4)=Sof(H4)=1-FVAR(2)
 Sof(S002)=Sof(C009)=Sof(H009)=Sof(C00K)=Sof(H00K)=Sof(C00L)=Sof(H00L)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C0(H0), C1(H1), C2(H2), C3(H3), C00M(H00M), C4(H4)
;
_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
S001 S 0.10198(6) 0.4334(2) 0.58727(5) 0.0418(3) Uani 1 1 d . . . . .
S002 S 0.31820(12) 1.0174(3) 0.67607(10) 0.0309(4) Uani 0.860(5) 1 d D . P A 1
S003 S 0.21552(11) -0.0711(3) 0.29869(8) 0.0295(4) Uani 0.699(4) 1 d D . P B 1
F004 F 0.33585(13) 0.3044(4) 0.37367(11) 0.0386(5) Uani 1 1 d . . . . .
F005 F 0.41413(13) 0.6730(4) 0.46831(11) 0.0413(5) Uani 1 1 d . . . . .
C006 C 0.0991(4) -0.1147(10) 0.3754(3) 0.0215(11) Uani 0.699(4) 1 d D . P B 1
H006 H 0.066823 -0.097179 0.413858 0.026 Uiso 0.699(4) 1 calc R . P B 1
N007 N 0.11015(17) 0.2593(6) 0.51157(14) 0.0291(6) Uani 1 1 d . . . . .
N008 N 0.18745(17) 0.6270(6) 0.60411(15) 0.0291(6) Uani 1 1 d . . . . .
C009 C 0.4356(4) 1.0309(11) 0.6003(3) 0.0281(11) Uani 0.860(5) 1 d D . P A 1
H009 H 0.468550 0.996664 0.563057 0.034 Uiso 0.860(5) 1 calc R . P A 1
C00A C 0.31070(19) 0.6835(6) 0.54412(16) 0.0230(6) Uani 1 1 d . . . . .
C00B C 0.22943(19) 0.5597(6) 0.54930(16) 0.0220(6) Uani 1 1 d . . . . .
C00C C 0.21833(19) 0.2484(6) 0.43199(16) 0.0224(6) Uani 1 1 d . . . . .
C00D C 0.18478(19) 0.3489(6) 0.49547(16) 0.0229(6) Uani 1 1 d . . . . .
C00E C 0.2949(2) 0.3742(6) 0.42940(17) 0.0257(7) Uani 1 1 d . . . . .
C00F C 0.3390(2) 0.5817(6) 0.48292(17) 0.0253(7) Uani 1 1 d . . . . .
C00G C 0.1735(2) 0.0355(6) 0.37646(16) 0.0246(6) Uani 1 1 d D . . . .
C00H C 0.3570(2) 0.8958(6) 0.59892(17) 0.0256(7) Uani 1 1 d D . . . .
C00I C 0.1345(10) -0.302(3) 0.2673(8) 0.028(3) Uani 0.699(4) 1 d D . P B 1
H00I H 0.130418 -0.421513 0.223641 0.033 Uiso 0.699(4) 1 calc R . P B 1
C00J C 0.0757(11) -0.299(3) 0.3106(9) 0.035(3) Uani 0.699(4) 1 d D . P B 1
H00J H 0.023931 -0.409499 0.298913 0.042 Uiso 0.699(4) 1 calc R . P B 1
C00K C 0.4613(8) 1.223(2) 0.6620(7) 0.037(3) Uani 0.860(5) 1 d D . P A 1
H00K H 0.513742 1.329357 0.671337 0.044 Uiso 0.860(5) 1 calc R . P A 1
C00L C 0.4041(6) 1.2391(19) 0.7065(6) 0.036(3) Uani 0.860(5) 1 d D . P A 1
H00L H 0.410979 1.361019 0.750155 0.043 Uiso 0.860(5) 1 calc R . P A 1
S0 S 0.0721(2) -0.0993(8) 0.3844(2) 0.0256(11) Uiso 0.301(4) 1 d D . P B 2
C0 C 0.1914(8) -0.085(3) 0.3140(7) 0.022(4) Uiso 0.301(4) 1 d D . P B 2
H0 H 0.242493 -0.039008 0.297514 0.027 Uiso 0.301(4) 1 calc R . P B 2
C1 C 0.130(2) -0.286(9) 0.274(2) 0.039(12) Uiso 0.301(4) 1 d D . P B 2
H1 H 0.132758 -0.379321 0.226977 0.047 Uiso 0.301(4) 1 calc R . P B 2
C2 C 0.0660(19) -0.326(6) 0.3110(19) 0.018(6) Uiso 0.301(4) 1 d D . P B 2
H2 H 0.022410 -0.467335 0.297139 0.021 Uiso 0.301(4) 1 calc R . P B 2
C3 C 0.333(3) 1.027(10) 0.661(2) 0.06(2) Uiso 0.140(5) 1 d D . P A 2
H3 H 0.281546 0.989042 0.676712 0.073 Uiso 0.140(5) 1 calc R . P A 2
S1 S 0.4568(7) 1.013(2) 0.5891(7) 0.036(3) Uiso 0.140(5) 1 d D . P A 2
C00M C 0.464(3) 1.255(12) 0.661(4) 0.017(13) Uiso 0.140(5) 1 d D . P A 2
H00M H 0.508323 1.393755 0.674297 0.020 Uiso 0.140(5) 1 calc R . P A 2
C4 C 0.398(3) 1.225(13) 0.696(3) 0.04(2) Uiso 0.140(5) 1 d D . P A 2
H4 H 0.394872 1.329394 0.741071 0.045 Uiso 0.140(5) 1 calc R . P A 2


_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
S001 N007 1.608(3) . ?
S001 N008 1.599(3) . ?
S002 C00H 1.731(4) . ?
S002 C00L 1.697(8) . ?
S003 C00G 1.747(3) . ?
S003 C00I 1.672(10) . ?
F004 C00E 1.349(3) . ?
F005 C00F 1.348(3) . ?
C006 C00G 1.372(7) . ?
C006 C00J 1.418(13) . ?
N007 C00D 1.349(4) . ?
N008 C00B 1.344(4) . ?
C009 C00H 1.393(7) . ?
C009 C00K 1.403(9) . ?
C00A C00B 1.436(4) . ?
C00A C00F 1.361(4) . ?
C00A C00H 1.463(4) . ?
C00B C00D 1.440(4) . ?
C00C C00D 1.439(4) . ?
C00C C00E 1.361(4) . ?
C00C C00G 1.464(4) . ?
C00E C00F 1.424(4) . ?
C00G S0 1.763(5) . ?
C00G C0 1.336(12) . ?
C00H C3 1.39(2) . ?
C00H S1 1.720(10) . ?
C00I C00J 1.343(10) . ?
C00K C00L 1.342(7) . ?
S0 C2 1.67(2) . ?
C0 C1 1.43(2) . ?
C1 C2 1.347(16) . ?
C3 C4 1.41(2) . ?
S1 C00M 1.70(2) . ?
C00M C4 1.349(18) . ?

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
N008 S001 N007 102.22(14) . . ?
C00L S002 C00H 92.6(3) . . ?
C00I S003 C00G 92.4(5) . . ?
C00G C006 C00J 112.4(7) . . ?
C00D N007 S001 105.7(2) . . ?
C00B N008 S001 105.9(2) . . ?
C00H C009 C00K 113.3(6) . . ?
C00B C00A C00H 123.2(3) . . ?
C00F C00A C00B 112.5(3) . . ?
C00F C00A C00H 124.3(3) . . ?
N008 C00B C00A 124.0(3) . . ?
N008 C00B C00D 113.3(3) . . ?
C00A C00B C00D 122.7(3) . . ?
C00D C00C C00G 122.9(3) . . ?
C00E C00C C00D 112.6(3) . . ?
C00E C00C C00G 124.5(3) . . ?
N007 C00D C00B 112.9(3) . . ?
N007 C00D C00C 124.9(3) . . ?
C00C C00D C00B 122.2(3) . . ?
F004 C00E C00C 120.6(3) . . ?
F004 C00E C00F 114.4(3) . . ?
C00C C00E C00F 125.0(3) . . ?
F005 C00F C00A 121.3(3) . . ?
F005 C00F C00E 113.8(3) . . ?
C00A C00F C00E 125.0(3) . . ?
C006 C00G S003 109.4(3) . . ?
C006 C00G C00C 129.7(3) . . ?
C00C C00G S003 120.9(2) . . ?
C00C C00G S0 119.6(2) . . ?
C0 C00G C00C 133.2(6) . . ?
C0 C00G S0 107.2(6) . . ?
C009 C00H S002 108.8(3) . . ?
C009 C00H C00A 128.7(3) . . ?
C00A C00H S002 122.4(2) . . ?
C00A C00H S1 118.4(4) . . ?
C3 C00H C00A 130.1(15) . . ?
C3 C00H S1 111.5(15) . . ?
C00J C00I S003 112.7(11) . . ?
C00I C00J C006 113.0(12) . . ?
C00L C00K C009 113.0(8) . . ?
C00K C00L S002 112.3(7) . . ?
C2 S0 C00G 92.9(9) . . ?
C00G C0 C1 116.2(14) . . ?
C2 C1 C0 111(2) . . ?
C1 C2 S0 113(2) . . ?
C00H C3 C4 110(2) . . ?
C00M S1 C00H 92.0(13) . . ?
C4 C00M S1 111(2) . . ?
C00M C4 C3 115(2) . . ?


_olex2_exptl_crystal_mounting_method 'mounted on loop mounter'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.844
