# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

 
data_3a
 
_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         '3a'
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C12 H8 F4 N2 O S'
_chemical_formula_sum
 'C12 H8 F4 N2 O S' 
_chemical_formula_weight          304.26

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'
 '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'
 'F'  'F'   0.0171   0.0103
 '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                    5.7581(3)
_cell_length_b                    13.2226(6)
_cell_length_c                    16.3778(8)
_cell_angle_alpha                 90
_cell_angle_beta                  93.070(3)
_cell_angle_gamma                 90
_cell_volume                      1245.17(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     170(2)
_cell_measurement_reflns_used     3277
_cell_measurement_theta_min       0.497
_cell_measurement_theta_max       30.508
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.623          
_exptl_crystal_F_000              616
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.23
_exptl_crystal_size_mid           0.19
_exptl_crystal_size_min           0.06
_exptl_absorpt_coefficient_mu     0.306
_shelx_estimated_absorpt_T_min    0.933
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.6655
_exptl_absorpt_correction_T_max   0.7461
_exptl_absorpt_process_details    'SADABS'

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       170(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_radiation_monochromator   'horizonally mounted graphite crystal'
_diffrn_measurement_device_type   'KappaCCD'
_diffrn_measurement_device        '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method        'CCD'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9840
_diffrn_reflns_av_unetI/netI      0.0704
_diffrn_reflns_av_R_equivalents   0.0597
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          1.981
_diffrn_reflns_theta_max          26.249
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              2501
_reflns_number_gt                 1487
_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        'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction         'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution     'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement   'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material   ?
_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)+(0.0091P)²+1.5902P] 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          2501
_refine_ls_number_parameters      182
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1201
_refine_ls_R_factor_gt            0.0655
_refine_ls_wR_factor_ref          0.1211
_refine_ls_wR_factor_gt           0.1013
_refine_ls_goodness_of_fit_ref    1.035
_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
S1 S 0.63401(17) 0.13099(7) 0.42893(6) 0.0483(3) Uani 1 1 d . . . . .
F1 F 1.0826(4) 0.21748(17) 0.62422(13) 0.0657(7) Uani 1 1 d . . . . .
F2 F 1.0430(4) 0.38593(18) 0.71370(15) 0.0799(8) Uani 1 1 d . . . . .
F3 F 0.3677(5) 0.4707(2) 0.58074(16) 0.0876(8) Uani 1 1 d . . . . .
F4 F 0.3668(4) 0.30492(18) 0.48849(14) 0.0726(7) Uani 1 1 d . . . . .
O1 O 0.3942(4) 0.1011(2) 0.42133(17) 0.0666(8) Uani 1 1 d . . . . .
N1 N 0.7046(6) 0.4282(3) 0.6485(2) 0.0624(9) Uani 1 1 d . . . . .
N2 N 0.7522(5) 0.1593(2) 0.51238(17) 0.0509(8) Uani 1 1 d . . . . .
C1 C 0.8963(6) 0.2777(3) 0.6114(2) 0.0473(9) Uani 1 1 d . . . . .
C2 C 0.8768(7) 0.3638(3) 0.6557(2) 0.0569(10) Uani 1 1 d . . . . .
C3 C 0.5453(7) 0.4049(3) 0.5913(3) 0.0588(11) Uani 1 1 d . . . . .
C4 C 0.5447(6) 0.3204(3) 0.5437(2) 0.0511(10) Uani 1 1 d . . . . .
C5 C 0.7251(6) 0.2507(3) 0.5520(2) 0.0451(9) Uani 1 1 d . . . . .
C6 C 0.8052(7) 0.0292(3) 0.3995(2) 0.0599(11) Uani 1 1 d . . . . .
H6A H 0.789393 -0.026947 0.437912 0.090 Uiso 1 1 calc R U . . .
H6B H 0.968393 0.050292 0.399929 0.090 Uiso 1 1 calc R U . . .
H6C H 0.753558 0.007295 0.344364 0.090 Uiso 1 1 calc R U . . .
C7 C 0.6785(6) 0.2287(3) 0.3576(2) 0.0414(8) Uani 1 1 d . . . . .
C8 C 0.8848(6) 0.2836(3) 0.3631(2) 0.0469(9) Uani 1 1 d . . . . .
H8 H 1.004050 0.267301 0.403316 0.056 Uiso 1 1 calc R U . . .
C9 C 0.9128(7) 0.3620(3) 0.3093(2) 0.0553(10) Uani 1 1 d . . . . .
H9 H 1.052724 0.400205 0.312263 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7403(7) 0.3853(3) 0.2514(2) 0.0575(10) Uani 1 1 d . . . . .
H10 H 0.760372 0.440047 0.214838 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5398(7) 0.3301(3) 0.2461(2) 0.0613(11) Uani 1 1 d . . . . .
H11 H 0.422028 0.346419 0.205368 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5058(6) 0.2508(3) 0.2990(2) 0.0513(10) Uani 1 1 d . . . . .
H12 H 0.366260 0.212343 0.295090 0.062 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 O1 1.436(3) . ?
S1 N2 1.540(3) . ?
S1 C6 1.751(4) . ?
S1 C7 1.770(4) . ?
F1 C1 1.343(4) . ?
F2 C2 1.343(4) . ?
F3 C3 1.347(4) . ?
F4 C4 1.345(4) . ?
N1 C2 1.308(5) . ?
N1 C3 1.311(5) . ?
N2 C5 1.385(4) . ?
C1 C2 1.358(5) . ?
C1 C5 1.394(5) . ?
C3 C4 1.362(5) . ?
C4 C5 1.389(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.375(4) . ?
C7 C8 1.391(5) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 H12 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
O1 S1 N2 121.41(18) . . ?
O1 S1 C6 108.50(18) . . ?
N2 S1 C6 101.65(17) . . ?
O1 S1 C7 108.45(16) . . ?
N2 S1 C7 109.63(16) . . ?
C6 S1 C7 106.05(18) . . ?
C2 N1 C3 114.2(4) . . ?
C5 N2 S1 124.9(3) . . ?
F1 C1 C2 120.1(3) . . ?
F1 C1 C5 119.1(3) . . ?
C2 C1 C5 120.8(4) . . ?
N1 C2 F2 115.5(4) . . ?
N1 C2 C1 125.5(4) . . ?
F2 C2 C1 118.9(4) . . ?
N1 C3 F3 115.9(4) . . ?
N1 C3 C4 125.6(4) . . ?
F3 C3 C4 118.5(4) . . ?
F4 C4 C3 119.2(4) . . ?
F4 C4 C5 120.2(3) . . ?
C3 C4 C5 120.6(3) . . ?
N2 C5 C4 129.4(3) . . ?
N2 C5 C1 117.2(3) . . ?
C4 C5 C1 113.3(3) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 121.2(3) . . ?
C12 C7 S1 119.4(3) . . ?
C8 C7 S1 119.4(3) . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 118.5(4) . . ?
C7 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
 
_refine_diff_density_max    0.230
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.055



