# 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_elmcg230419
_database_code_depnum_ccdc_archive 'CCDC 2301994'
loop_
_audit_author_name
_audit_author_address
Gruber
;University of Strasbourg
France
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 F3 N O4 S'
_chemical_formula_sum            'C19 H18 F3 N O4 S'
_chemical_formula_weight         413.40

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9278(3)
_cell_length_b                   16.1864(4)
_cell_length_c                   12.2047(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.3770(10)
_cell_angle_gamma                90
_cell_volume                     1838.51(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9234
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29538
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         27.913
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4381
_reflns_number_gt                4013
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0569P)²+1.2971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4381
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_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
N1 N 0.45193(12) 0.80766(7) 0.59116(11) 0.0200(2) Uani 1 1 d . . . . .
S1 S 0.39648(3) 0.89714(2) 0.62517(3) 0.01896(10) Uani 1 1 d . . . . .
O1 O 0.38215(11) 0.88552(7) 0.73707(9) 0.0251(2) Uani 1 1 d . . . . .
O2 O 0.49263(11) 0.95858(7) 0.61049(10) 0.0262(2) Uani 1 1 d . . . . .
C1 C 0.22521(14) 0.91449(8) 0.52089(12) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.10602(15) 0.88650(9) 0.54502(13) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.117181 0.862665 0.618804 0.027 Uiso 1 1 calc R U . . .
C3 C -0.02935(16) 0.89382(9) 0.46008(14) 0.0250(3) Uani 1 1 d . . . . .
H3 H -0.110904 0.874360 0.476044 0.030 Uiso 1 1 calc R U . . .
C4 C -0.04768(16) 0.92908(9) 0.35214(13) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.07345(17) 0.95892(10) 0.33091(13) 0.0265(3) Uani 1 1 d . . . . .
H5 H 0.061771 0.984473 0.258101 0.032 Uiso 1 1 calc R U . . .
C6 C 0.20994(16) 0.95191(9) 0.41401(13) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.291448 0.972107 0.398640 0.027 Uiso 1 1 calc R U . . .
C7 C -0.19580(18) 0.93568(12) 0.26124(16) 0.0367(4) Uani 1 1 d . . . . .
H7A H -0.205763 0.895433 0.198915 0.055 Uiso 1 1 calc R U . . .
H7B H -0.210157 0.991548 0.228221 0.055 Uiso 1 1 calc R U . . .
H7C H -0.267844 0.924365 0.297437 0.055 Uiso 1 1 calc R U . . .
C8 C 0.52545(14) 0.80392(9) 0.50550(12) 0.0209(3) Uani 1 1 d . . . . .
H8A H 0.520037 0.858735 0.468229 0.025 Uiso 1 1 calc R U . . .
H8B H 0.475545 0.763631 0.443641 0.025 Uiso 1 1 calc R U . . .
C9 C 0.68209(14) 0.77886(9) 0.56140(12) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.74235(15) 0.72141(9) 0.50753(13) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.683478 0.696457 0.436562 0.027 Uiso 1 1 calc R U . . .
C11 C 0.88840(16) 0.69917(9) 0.55530(14) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.930178 0.660664 0.517766 0.029 Uiso 1 1 calc R U . . .
C12 C 0.96702(14) 0.73616(9) 0.65901(13) 0.0213(3) Uani 1 1 d . . . . .
O3 O 1.11222(11) 0.72800(7) 0.72253(10) 0.0265(2) Uani 1 1 d . . . . .
C13 C 1.13485(16) 0.77402(11) 0.82806(14) 0.0285(3) Uani 1 1 d . . . . .
H13A H 1.148549 0.735833 0.894434 0.034 Uiso 1 1 calc R U . . .
H13B H 1.221765 0.808898 0.845781 0.034 Uiso 1 1 calc R U . . .
O4 O 1.01106(11) 0.82470(8) 0.81091(10) 0.0300(3) Uani 1 1 d . . . . .
C14 C 0.90741(15) 0.79353(9) 0.71269(12) 0.0213(3) Uani 1 1 d . . . . .
C15 C 0.76597(15) 0.81681(9) 0.66690(12) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.726534 0.856557 0.704476 0.026 Uiso 1 1 calc R U . . .
C16 C 0.40499(15) 0.73502(9) 0.63000(12) 0.0211(3) Uani 1 1 d . . . . .
H16 H 0.347605 0.741688 0.677510 0.025 Uiso 1 1 calc R U . . .
C17 C 0.43291(16) 0.65804(9) 0.60687(13) 0.0250(3) Uani 1 1 d . . . . .
H17 H 0.485767 0.647852 0.556632 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3804(2) 0.58714(10) 0.66067(15) 0.0324(4) Uani 1 1 d . . . . .
H18A H 0.464578 0.557012 0.713839 0.039 Uiso 1 1 calc R U . . .
H18B H 0.326166 0.609554 0.708466 0.039 Uiso 1 1 calc R U . . .
C19 C 0.28786(19) 0.52818(11) 0.57547(15) 0.0323(4) Uani 1 1 d . . . . .
F1 F 0.17068(14) 0.56358(9) 0.49969(13) 0.0639(4) Uani 1 1 d . . . . .
F2 F 0.24133(13) 0.46608(6) 0.62627(10) 0.0411(3) Uani 1 1 d . . . . .
F3 F 0.35893(17) 0.49127(8) 0.51273(12) 0.0590(4) Uani 1 1 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
N1 C16 1.4064(18) . ?
N1 C8 1.4701(18) . ?
N1 S1 1.6529(12) . ?
S1 O2 1.4323(11) . ?
S1 O1 1.4339(11) . ?
S1 C1 1.7559(14) . ?
C1 C2 1.3910(19) . ?
C1 C6 1.398(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.401(2) . ?
C4 C7 1.506(2) . ?
C5 C6 1.386(2) . ?
C8 C9 1.5197(18) . ?
C9 C10 1.3888(19) . ?
C9 C15 1.4078(19) . ?
C10 C11 1.408(2) . ?
C11 C12 1.372(2) . ?
C12 C14 1.383(2) . ?
C12 O3 1.3850(17) . ?
O3 C13 1.436(2) . ?
C13 O4 1.4310(19) . ?
O4 C14 1.3752(17) . ?
C14 C15 1.3710(19) . ?
C16 C17 1.328(2) . ?
C17 C18 1.503(2) . ?
C18 C19 1.473(2) . ?
C19 F1 1.337(2) . ?
C19 F2 1.3445(19) . ?
C19 F3 1.348(2) . ?

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
C16 N1 C8 120.67(12) . . ?
C16 N1 S1 118.00(10) . . ?
C8 N1 S1 120.39(10) . . ?
O2 S1 O1 120.11(7) . . ?
O2 S1 N1 106.40(6) . . ?
O1 S1 N1 106.05(6) . . ?
O2 S1 C1 108.52(7) . . ?
O1 S1 C1 108.61(7) . . ?
N1 S1 C1 106.34(6) . . ?
C2 C1 C6 121.00(13) . . ?
C2 C1 S1 118.35(11) . . ?
C6 C1 S1 120.58(11) . . ?
C3 C2 C1 119.21(14) . . ?
C2 C3 C4 121.13(14) . . ?
C3 C4 C5 118.67(13) . . ?
C3 C4 C7 119.99(15) . . ?
C5 C4 C7 121.33(15) . . ?
C6 C5 C4 121.33(14) . . ?
C5 C6 C1 118.62(13) . . ?
N1 C8 C9 112.06(11) . . ?
C10 C9 C15 120.66(13) . . ?
C10 C9 C8 120.55(13) . . ?
C15 C9 C8 118.76(12) . . ?
C9 C10 C11 121.76(13) . . ?
C12 C11 C10 116.32(13) . . ?
C11 C12 C14 122.04(13) . . ?
C11 C12 O3 128.44(14) . . ?
C14 C12 O3 109.43(13) . . ?
C12 O3 C13 105.06(11) . . ?
O4 C13 O3 107.94(12) . . ?
C14 O4 C13 105.13(12) . . ?
C15 C14 O4 127.14(14) . . ?
C15 C14 C12 122.55(13) . . ?
O4 C14 C12 110.22(12) . . ?
C14 C15 C9 116.65(13) . . ?
C17 C16 N1 126.48(13) . . ?
C16 C17 C18 119.58(14) . . ?
C19 C18 C17 114.34(14) . . ?
F1 C19 F2 106.47(14) . . ?
F1 C19 F3 107.37(16) . . ?
F2 C19 F3 105.21(14) . . ?
F1 C19 C18 112.89(15) . . ?
F2 C19 C18 112.87(14) . . ?
F3 C19 C18 111.53(15) . . ?

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
C16 N1 S1 O2 161.56(10) . . . . ?
C8 N1 S1 O2 -29.42(12) . . . . ?
C16 N1 S1 O1 32.60(12) . . . . ?
C8 N1 S1 O1 -158.38(10) . . . . ?
C16 N1 S1 C1 -82.89(11) . . . . ?
C8 N1 S1 C1 86.13(11) . . . . ?
O2 S1 C1 C2 -154.78(11) . . . . ?
O1 S1 C1 C2 -22.63(13) . . . . ?
N1 S1 C1 C2 91.12(12) . . . . ?
O2 S1 C1 C6 28.30(14) . . . . ?
O1 S1 C1 C6 160.45(11) . . . . ?
N1 S1 C1 C6 -85.80(12) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
S1 C1 C2 C3 -175.00(11) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 C7 179.57(14) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C7 C4 C5 C6 -179.18(14) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
S1 C1 C6 C5 175.33(11) . . . . ?
C16 N1 C8 C9 -78.52(16) . . . . ?
S1 N1 C8 C9 112.76(12) . . . . ?
N1 C8 C9 C10 136.17(14) . . . . ?
N1 C8 C9 C15 -45.73(17) . . . . ?
C15 C9 C10 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 177.79(13) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C10 C11 C12 C14 -1.4(2) . . . . ?
C10 C11 C12 O3 -177.51(13) . . . . ?
C11 C12 O3 C13 -174.94(15) . . . . ?
C14 C12 O3 C13 8.54(15) . . . . ?
C12 O3 C13 O4 -14.37(15) . . . . ?
O3 C13 O4 C14 14.73(15) . . . . ?
C13 O4 C14 C15 173.86(15) . . . . ?
C13 O4 C14 C12 -9.54(16) . . . . ?
C11 C12 C14 C15 0.6(2) . . . . ?
O3 C12 C14 C15 177.40(13) . . . . ?
C11 C12 C14 O4 -176.16(13) . . . . ?
O3 C12 C14 O4 0.62(16) . . . . ?
O4 C14 C15 C9 176.59(13) . . . . ?
C12 C14 C15 C9 0.4(2) . . . . ?
C10 C9 C15 C14 -0.5(2) . . . . ?
C8 C9 C15 C14 -178.63(13) . . . . ?
C8 N1 C16 C17 7.8(2) . . . . ?
S1 N1 C16 C17 176.77(12) . . . . ?
N1 C16 C17 C18 176.88(14) . . . . ?
C16 C17 C18 C19 122.82(17) . . . . ?
C17 C18 C19 F1 -58.5(2) . . . . ?
C17 C18 C19 F2 -179.27(14) . . . . ?
C17 C18 C19 F3 62.5(2) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.053

