# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2325553'
_audit_update_record             
;
2024-01-15 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6374)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 F3 N2 O S'
_chemical_formula_sum            'C18 H13 F3 N2 O S'
_chemical_formula_weight         362.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7880(12)
_cell_length_b                   10.509(3)
_cell_length_c                   16.019(4)
_cell_angle_alpha                90.169(3)
_cell_angle_beta                 91.422(3)
_cell_angle_gamma                90.026(3)
_cell_volume                     805.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3241
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9105
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_min         1.272
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2762
_reflns_number_total             3587
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.052
_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)+(0.0728P)²+0.1409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1340
_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:
 C14(H14), C2(H2), C17(H17), C7(H7), C15(H15), C16(H16), C9(H9), C5(H5),
 C6(H6), C8(H8)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.23970(14) 0.69874(5) 0.66306(3) 0.0641(2) Uani 1 1 d . . . . .
F2 F 0.2528(3) 0.66908(15) 0.50159(8) 0.0843(4) Uani 1 1 d . . . . .
F3 F -0.1264(3) 0.61629(14) 0.55186(10) 0.0843(4) Uani 1 1 d . . . . .
F1 F -0.0186(4) 0.81305(13) 0.54658(9) 0.0950(5) Uani 1 1 d . . . . .
O1 O 0.2536(3) 0.28321(13) 0.62873(9) 0.0648(4) Uani 1 1 d . . . . .
N1 N 0.7166(3) 0.32650(13) 0.80332(9) 0.0435(3) Uani 1 1 d . . . . .
N2 N 0.5818(3) 0.14785(13) 0.67999(9) 0.0461(4) Uani 1 1 d . . . . .
C4 C 0.4489(4) 0.56440(15) 0.81922(10) 0.0409(4) Uani 1 1 d . . . . .
C13 C 0.8343(4) 0.20626(15) 0.80461(11) 0.0414(4) Uani 1 1 d . . . . .
C10 C 0.5408(4) 0.35539(15) 0.74367(10) 0.0404(4) Uani 1 1 d . . . . .
C12 C 0.7752(4) 0.11623(15) 0.74219(10) 0.0426(4) Uani 1 1 d . . . . .
C3 C 0.4358(4) 0.48782(16) 0.74068(11) 0.0435(4) Uani 1 1 d . . . . .
C11 C 0.4429(4) 0.26237(17) 0.67893(11) 0.0461(4) Uani 1 1 d . . . . .
C14 C 1.0245(4) 0.17615(18) 0.86866(12) 0.0528(5) Uani 1 1 d . . . . .
H14 H 1.063835 0.235737 0.910358 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3409(4) 0.53930(17) 0.66921(11) 0.0506(4) Uani 1 1 d . . . . .
H2 H 0.328445 0.488832 0.621472 0.061 Uiso 1 1 calc R U . . .
C17 C 0.9093(4) -0.00202(17) 0.74556(13) 0.0547(5) Uani 1 1 d . . . . .
H17 H 0.871477 -0.062625 0.704393 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4524(4) 0.71213(19) 0.96315(13) 0.0567(5) Uani 1 1 d . . . . .
H7 H 0.453548 0.761150 1.011588 0.068 Uiso 1 1 calc R U . . .
C1 C 0.0810(5) 0.69714(18) 0.56105(12) 0.0554(5) Uani 1 1 d . . . . .
C15 C 1.1548(5) 0.06015(19) 0.87123(14) 0.0597(5) Uani 1 1 d . . . . .
H15 H 1.281751 0.041103 0.914262 0.072 Uiso 1 1 calc R U . . .
C16 C 1.0953(4) -0.02878(18) 0.80896(14) 0.0601(5) Uani 1 1 d . . . . .
H16 H 1.183538 -0.107594 0.810505 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5133(6) 0.0574(2) 0.61252(13) 0.0673(6) Uani 1 1 d . . . . .
H18A H 0.678754 0.038478 0.582201 0.101 Uiso 1 1 calc R U . . .
H18B H 0.375350 0.094130 0.575376 0.101 Uiso 1 1 calc R U . . .
H18C H 0.441056 -0.019551 0.635879 0.101 Uiso 1 1 calc R U . . .
C9 C 0.2768(5) 0.5370(2) 0.88311(14) 0.0692(6) Uani 1 1 d . . . . .
H9 H 0.155534 0.468053 0.878343 0.083 Uiso 1 1 calc R U . . .
C5 C 0.6237(5) 0.6687(2) 0.82858(14) 0.0663(6) Uani 1 1 d . . . . .
H5 H 0.743772 0.689955 0.786044 0.080 Uiso 1 1 calc R U . . .
C6 C 0.6215(5) 0.7413(2) 0.90044(14) 0.0687(6) Uani 1 1 d . . . . .
H6 H 0.739036 0.811547 0.905496 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2797(6) 0.6102(2) 0.95499(15) 0.0803(8) Uani 1 1 d . . . . .
H8 H 0.162058 0.589352 0.998211 0.096 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 1.7468(18) . ?
S1 C1 1.785(2) . ?
F2 C1 1.307(2) . ?
F3 C1 1.312(2) . ?
F1 C1 1.327(2) . ?
O1 C11 1.217(2) . ?
N1 C13 1.384(2) . ?
N1 C10 1.295(2) . ?
N2 C12 1.384(2) . ?
N2 C11 1.375(2) . ?
N2 C18 1.468(2) . ?
C4 C3 1.492(2) . ?
C4 C9 1.361(3) . ?
C4 C5 1.384(3) . ?
C13 C12 1.398(2) . ?
C13 C14 1.392(3) . ?
C10 C3 1.480(2) . ?
C10 C11 1.490(2) . ?
C12 C17 1.400(2) . ?
C3 C2 1.337(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(3) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.364(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.342(3) . ?
C7 C8 1.357(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C8 H8 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
C2 S1 C1 99.01(9) . . ?
C10 N1 C13 118.98(14) . . ?
C12 N2 C18 120.44(16) . . ?
C11 N2 C12 122.39(14) . . ?
C11 N2 C18 117.16(16) . . ?
C9 C4 C3 120.39(16) . . ?
C9 C4 C5 117.60(17) . . ?
C5 C4 C3 121.93(17) . . ?
N1 C13 C12 122.03(15) . . ?
N1 C13 C14 118.66(15) . . ?
C14 C13 C12 119.28(15) . . ?
N1 C10 C3 117.44(14) . . ?
N1 C10 C11 123.11(15) . . ?
C3 C10 C11 119.45(15) . . ?
N2 C12 C13 118.09(15) . . ?
N2 C12 C17 122.76(16) . . ?
C13 C12 C17 119.14(17) . . ?
C10 C3 C4 118.07(14) . . ?
C2 C3 C4 120.66(15) . . ?
C2 C3 C10 121.23(15) . . ?
O1 C11 N2 121.31(16) . . ?
O1 C11 C10 123.85(16) . . ?
N2 C11 C10 114.84(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.05(18) . . ?
C15 C14 H14 119.5 . . ?
S1 C2 H2 119.1 . . ?
C3 C2 S1 121.80(14) . . ?
C3 C2 H2 119.1 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.30(17) . . ?
C16 C17 H17 119.8 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.16(18) . . ?
C8 C7 H7 120.4 . . ?
F2 C1 S1 114.05(15) . . ?
F2 C1 F3 105.17(17) . . ?
F2 C1 F1 107.95(17) . . ?
F3 C1 S1 114.26(14) . . ?
F3 C1 F1 107.86(18) . . ?
F1 C1 S1 107.27(13) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.36(19) . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.87(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C9 H9 119.5 . . ?
C4 C9 C8 120.93(19) . . ?
C8 C9 H9 119.5 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.99(19) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 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
N1 C13 C12 N2 -3.3(3) . . . . ?
N1 C13 C12 C17 177.63(16) . . . . ?
N1 C13 C14 C15 -177.63(18) . . . . ?
N1 C10 C3 C4 -22.2(2) . . . . ?
N1 C10 C3 C2 155.51(18) . . . . ?
N1 C10 C11 O1 170.73(18) . . . . ?
N1 C10 C11 N2 -8.6(3) . . . . ?
N2 C12 C17 C16 -179.08(18) . . . . ?
C4 C3 C2 S1 2.3(3) . . . . ?
C4 C9 C8 C7 0.7(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C13 N1 C10 C3 -175.43(15) . . . . ?
C13 N1 C10 C11 4.3(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C10 N1 C13 C12 1.8(3) . . . . ?
C10 N1 C13 C14 179.59(17) . . . . ?
C10 C3 C2 S1 -175.35(14) . . . . ?
C12 N2 C11 O1 -172.37(17) . . . . ?
C12 N2 C11 C10 7.0(2) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C17 C16 C15 0.1(3) . . . . ?
C3 C4 C9 C8 -177.6(2) . . . . ?
C3 C4 C5 C6 176.9(2) . . . . ?
C3 C10 C11 O1 -9.5(3) . . . . ?
C3 C10 C11 N2 171.09(15) . . . . ?
C11 N2 C12 C13 -1.6(2) . . . . ?
C11 N2 C12 C17 177.40(17) . . . . ?
C11 C10 C3 C4 158.08(16) . . . . ?
C11 C10 C3 C2 -24.2(3) . . . . ?
C14 C13 C12 N2 178.96(16) . . . . ?
C14 C13 C12 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C2 S1 C1 F2 -62.53(17) . . . . ?
C2 S1 C1 F3 58.50(17) . . . . ?
C2 S1 C1 F1 177.99(16) . . . . ?
C1 S1 C2 C3 -169.97(18) . . . . ?
C18 N2 C12 C13 179.52(17) . . . . ?
C18 N2 C12 C17 -1.4(3) . . . . ?
C18 N2 C11 O1 6.5(3) . . . . ?
C18 N2 C11 C10 -174.11(17) . . . . ?
C9 C4 C3 C10 -70.7(2) . . . . ?
C9 C4 C3 C2 111.6(2) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C5 C4 C3 C10 112.6(2) . . . . ?
C5 C4 C3 C2 -65.1(3) . . . . ?
C5 C4 C9 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C8 C7 C6 C5 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
