# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3m
_database_code_depnum_ccdc_archive 'CCDC 2211357'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse 
France
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F6 N O S'
_chemical_formula_weight         367.31

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'
O O 0.0106 0.0060 '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'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.173(4)
_cell_length_b                   7.530(4)
_cell_length_c                   17.450(10)
_cell_angle_alpha                99.942(15)
_cell_angle_beta                 93.614(16)
_cell_angle_gamma                95.649(16)
_cell_volume                     792.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    1406
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      19.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture Photon III-C14 detector'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            21071
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_av_R_equivalents  0.1684
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3248
_reflns_number_gt                1454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²+0.3677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     308
_refine_ls_number_restraints     365
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C3 C 0.4965(8) 0.5399(6) 0.7609(2) 0.0494(11) Uani 1 1 d D . . . .
N1 N 0.4261(8) 0.6198(6) 0.8353(2) 0.0590(14) Uani 0.915(3) 1 d D . P A 1
S1 S 0.4514(3) 0.8438(2) 0.86364(9) 0.0706(5) Uani 0.915(3) 1 d D U P A 1
C1 C 0.7197(12) 0.8873(9) 0.9117(4) 0.0799(16) Uani 0.915(3) 1 d D U P A 1
F1 F 0.8734(6) 0.8300(6) 0.8672(2) 0.0952(12) Uani 0.915(3) 1 d D U P A 1
F2 F 0.7700(11) 1.0631(8) 0.9340(4) 0.136(2) Uani 0.915(3) 1 d D U P A 1
F3 F 0.7426(7) 0.8157(8) 0.9746(2) 0.1246(17) Uani 0.915(3) 1 d D U P A 1
C2 C 0.3268(10) 0.5016(9) 0.8802(3) 0.0701(15) Uani 0.915(3) 1 d D U P A 1
F4 F 0.2446(8) 0.5850(7) 0.9413(2) 0.1067(16) Uani 0.915(3) 1 d D U P A 1
F5 F 0.4617(9) 0.3975(8) 0.9051(3) 0.1197(16) Uani 0.915(3) 1 d D U P A 1
F6 F 0.1704(9) 0.3878(9) 0.8380(2) 0.1255(18) Uani 0.915(3) 1 d D U P A 1
N1' N 0.494(6) 0.608(5) 0.8440(12) 0.076(3) Uani 0.085(3) 1 d D U P A 2
S1' S 0.688(3) 0.750(3) 0.9020(10) 0.086(3) Uani 0.085(3) 1 d D U P A 2
C1' C 0.594(5) 0.961(4) 0.8890(18) 0.087(3) Uani 0.085(3) 1 d D U P A 2
F1' F 0.607(6) 0.989(5) 0.8169(18) 0.093(6) Uani 0.085(3) 1 d D U P A 2
F2' F 0.718(8) 1.095(5) 0.935(3) 0.099(6) Uani 0.085(3) 1 d D U P A 2
F3' F 0.394(6) 0.984(5) 0.908(2) 0.099(6) Uani 0.085(3) 1 d D U P A 2
C2' C 0.331(5) 0.509(4) 0.8781(15) 0.085(3) Uani 0.085(3) 1 d D U P A 2
F4' F 0.132(5) 0.529(6) 0.853(2) 0.090(5) Uani 0.085(3) 1 d D U P A 2
F5' F 0.349(8) 0.335(4) 0.862(2) 0.082(5) Uani 0.085(3) 1 d D U P A 2
F6' F 0.358(7) 0.556(6) 0.9537(15) 0.092(5) Uani 0.085(3) 1 d D U P A 2
O1 O 0.6795(5) 0.3296(4) 0.54300(16) 0.0447(8) Uani 1 1 d . . . . .
C4 C 0.6785(8) 0.4481(6) 0.7563(3) 0.0540(12) Uani 1 1 d . . . . .
H4 H 0.758947 0.434727 0.802806 0.065 Uiso 1 1 calc R U . . .
C5 C 0.7456(8) 0.3746(6) 0.6841(2) 0.0480(11) Uani 1 1 d . . . . .
H5 H 0.871531 0.311386 0.681181 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6283(7) 0.3941(5) 0.6171(2) 0.0407(10) Uani 1 1 d . . . . .
C7 C 0.4463(7) 0.4902(6) 0.6216(2) 0.0428(10) Uani 1 1 d . . . . .
H7 H 0.367485 0.506742 0.575234 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3820(8) 0.5606(6) 0.6931(3) 0.0474(11) Uani 1 1 d . . . . .
H8 H 0.256729 0.624620 0.696088 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8699(7) 0.2336(6) 0.5351(2) 0.0478(11) Uani 1 1 d . . . . .
H9A H 0.857138 0.131064 0.563827 0.057 Uiso 1 1 calc R U . . .
H9B H 1.002234 0.316073 0.557377 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8879(7) 0.1644(5) 0.4504(2) 0.0421(10) Uani 1 1 d . . . . .
C11 C 0.7241(8) 0.0424(6) 0.4066(3) 0.0488(11) Uani 1 1 d . . . . .
H11 H 0.595650 0.006907 0.429940 0.059 Uiso 1 1 calc R U . . .
C12 C 0.7463(8) -0.0276(6) 0.3295(3) 0.0552(12) Uani 1 1 d . . . . .
H12 H 0.633000 -0.110672 0.300006 0.066 Uiso 1 1 calc R U . . .
C13 C 0.9322(8) 0.0223(6) 0.2948(3) 0.0527(12) Uani 1 1 d . . . . .
H13 H 0.947507 -0.026068 0.241691 0.063 Uiso 1 1 calc R U . . .
C14 C 1.0954(8) 0.1430(6) 0.3381(3) 0.0540(12) Uani 1 1 d . . . . .
H14 H 1.223898 0.178025 0.314709 0.065 Uiso 1 1 calc R U . . .
C15 C 1.0729(8) 0.2133(6) 0.4155(3) 0.0487(11) Uani 1 1 d . . . . .
H15 H 1.186490 0.296303 0.444843 0.058 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
C3 C4 1.375(6) . ?
C3 C8 1.380(6) . ?
C3 N1 1.446(6) . ?
C3 N1' 1.454(18) . ?
N1 C2 1.405(7) . ?
N1 S1 1.662(5) . ?
S1 C1 1.782(7) . ?
C1 F3 1.309(7) . ?
C1 F2 1.314(8) . ?
C1 F1 1.322(7) . ?
C2 F4 1.299(6) . ?
C2 F5 1.303(7) . ?
C2 F6 1.319(7) . ?
N1' C2' 1.418(19) . ?
N1' S1' 1.682(18) . ?
S1' C1' 1.786(19) . ?
C1' F2' 1.316(16) . ?
C1' F1' 1.318(15) . ?
C1' F3' 1.320(15) . ?
C2' F6' 1.302(15) . ?
C2' F4' 1.307(15) . ?
C2' F5' 1.308(15) . ?
O1 C6 1.368(5) . ?
O1 C9 1.441(5) . ?
C4 C5 1.391(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(6) . ?
C7 C8 1.368(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.495(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.376(6) . ?
C10 C11 1.389(6) . ?
C11 C12 1.378(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C4 C3 C8 119.4(4) . . ?
C4 C3 N1 121.3(4) . . ?
C8 C3 N1 119.2(4) . . ?
C4 C3 N1' 103(2) . . ?
C8 C3 N1' 137(2) . . ?
C2 N1 C3 117.5(4) . . ?
C2 N1 S1 121.9(4) . . ?
C3 N1 S1 120.5(3) . . ?
N1 S1 C1 102.0(3) . . ?
F3 C1 F2 106.4(6) . . ?
F3 C1 F1 106.0(6) . . ?
F2 C1 F1 106.4(6) . . ?
F3 C1 S1 114.2(5) . . ?
F2 C1 S1 109.4(5) . . ?
F1 C1 S1 113.9(5) . . ?
F4 C2 F5 106.7(5) . . ?
F4 C2 F6 108.3(6) . . ?
F5 C2 F6 104.4(6) . . ?
F4 C2 N1 113.4(6) . . ?
F5 C2 N1 112.5(5) . . ?
F6 C2 N1 111.0(5) . . ?
C2' N1' C3 112.0(16) . . ?
C2' N1' S1' 119.4(17) . . ?
C3 N1' S1' 127.1(18) . . ?
N1' S1' C1' 98.9(18) . . ?
F2' C1' F1' 107(2) . . ?
F2' C1' F3' 104(2) . . ?
F1' C1' F3' 108(2) . . ?
F2' C1' S1' 109(2) . . ?
F1' C1' S1' 112(2) . . ?
F3' C1' S1' 116(2) . . ?
F6' C2' F4' 110(2) . . ?
F6' C2' F5' 107(2) . . ?
F4' C2' F5' 106(2) . . ?
F6' C2' N1' 109(2) . . ?
F4' C2' N1' 114(3) . . ?
F5' C2' N1' 110(2) . . ?
C6 O1 C9 117.3(3) . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O1 C6 C5 124.8(4) . . ?
O1 C6 C7 115.1(4) . . ?
C5 C6 C7 120.1(4) . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C3 120.9(4) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
O1 C9 C10 108.7(3) . . ?
O1 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O1 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C15 C10 C11 118.8(4) . . ?
C15 C10 C9 120.4(4) . . ?
C11 C10 C9 120.8(4) . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.7(4) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?

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
C4 C3 N1 C2 -73.8(6) . . . . ?
C8 C3 N1 C2 107.9(6) . . . . ?
C4 C3 N1 S1 109.2(5) . . . . ?
C8 C3 N1 S1 -69.1(6) . . . . ?
C2 N1 S1 C1 94.8(5) . . . . ?
C3 N1 S1 C1 -88.3(5) . . . . ?
N1 S1 C1 F3 -64.6(5) . . . . ?
N1 S1 C1 F2 176.4(5) . . . . ?
N1 S1 C1 F1 57.4(5) . . . . ?
C3 N1 C2 F4 -172.0(5) . . . . ?
S1 N1 C2 F4 4.9(8) . . . . ?
C3 N1 C2 F5 66.7(7) . . . . ?
S1 N1 C2 F5 -116.4(6) . . . . ?
C3 N1 C2 F6 -49.9(7) . . . . ?
S1 N1 C2 F6 127.1(6) . . . . ?
C4 C3 N1' C2' -105(3) . . . . ?
C8 C3 N1' C2' 82(3) . . . . ?
C4 C3 N1' S1' 60(4) . . . . ?
C8 C3 N1' S1' -112(4) . . . . ?
C2' N1' S1' C1' -106(3) . . . . ?
C3 N1' S1' C1' 89(4) . . . . ?
N1' S1' C1' F2' 176(3) . . . . ?
N1' S1' C1' F1' -66(2) . . . . ?
N1' S1' C1' F3' 58(3) . . . . ?
C3 N1' C2' F6' 170(3) . . . . ?
S1' N1' C2' F6' 3(4) . . . . ?
C3 N1' C2' F4' -67(4) . . . . ?
S1' N1' C2' F4' 126(4) . . . . ?
C3 N1' C2' F5' 53(4) . . . . ?
S1' N1' C2' F5' -114(4) . . . . ?
C8 C3 C4 C5 -0.8(7) . . . . ?
N1 C3 C4 C5 -179.0(4) . . . . ?
N1' C3 C4 C5 -174.9(11) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C9 O1 C6 C5 0.3(6) . . . . ?
C9 O1 C6 C7 178.3(4) . . . . ?
C4 C5 C6 O1 179.3(4) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
O1 C6 C7 C8 -179.9(4) . . . . ?
C5 C6 C7 C8 -1.8(6) . . . . ?
C6 C7 C8 C3 0.9(6) . . . . ?
C4 C3 C8 C7 0.3(7) . . . . ?
N1 C3 C8 C7 178.7(4) . . . . ?
N1' C3 C8 C7 172.0(15) . . . . ?
C6 O1 C9 C10 176.2(3) . . . . ?
O1 C9 C10 C15 122.3(4) . . . . ?
O1 C9 C10 C11 -61.2(5) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
C9 C10 C11 C12 -176.9(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C11 C10 C15 C14 0.2(6) . . . . ?
C9 C10 C15 C14 176.9(4) . . . . ?
C13 C14 C15 C10 -0.1(7) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.063




#===END
