# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_NEt4ACPFSA_90K
_database_code_depnum_ccdc_archive 'CCDC 2239497'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Mochida'
;Kobe University
Japan
;
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            NEt4ACPFSA
_chemical_formula_moiety         C12H20F6N2O4S2
_chemical_formula_sum            'C12 H20 F6 N2 O4 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         434.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.447(6)
_cell_length_b                   10.992(3)
_cell_length_c                   17.992(7)
_cell_angle_alpha                90
_cell_angle_beta                 127.576(3)
_cell_angle_gamma                90
_cell_volume                     3675.(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2290
_cell_measurement_theta_min      2.1920
_cell_measurement_theta_max      27.6492
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792

_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10214
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             4189
_reflns_number_gt                2661
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1171
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_number_reflns         4189
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.6643P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.615
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'Generate Report (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.85414(4) 0.24426(7) 0.75894(5) 0.0364(2) Uani d . . . 1 . .
S S2 0.76935(4) 0.33699(6) 0.80167(5) 0.02328(17) Uani d . . . 1 . .
F F1 0.94743(10) 0.4035(3) 0.78474(14) 0.0782(7) Uani d . . . 1 . .
F F2 0.96866(9) 0.3328(2) 0.91296(12) 0.0707(7) Uani d . . . 1 . .
F F3 0.93263(11) 0.56419(19) 0.89007(13) 0.0662(7) Uani d . . . 1 . .
F F4 0.83784(9) 0.53624(15) 0.74572(11) 0.0410(4) Uani d . . . 1 . .
F F5 0.80301(9) 0.56188(13) 0.86051(11) 0.0418(5) Uani d . . . 1 . .
F F6 0.88199(8) 0.42712(14) 0.95769(10) 0.0355(4) Uani d . . . 1 . .
O O1 0.74791(11) 0.30486(18) 0.85834(13) 0.0377(5) Uani d . . . 1 . .
O O2 0.71650(9) 0.38419(16) 0.70978(12) 0.0276(4) Uani d . . . 1 . .
O O3 0.89828(14) 0.1404(2) 0.78122(15) 0.0701(9) Uani d . . . 1 . .
O O4 0.80866(10) 0.28349(17) 0.66360(12) 0.0303(5) Uani d . . . 1 . .
N N1 0.63037(10) 0.51382(18) 0.45226(13) 0.0190(5) Uani d . . . 1 . .
N N2 0.81820(12) 0.23169(19) 0.80942(15) 0.0305(6) Uani d . . . 1 . .
C C1 0.75844(14) 0.4794(3) 0.50705(19) 0.0309(7) Uani d . . . 1 . .
H H1A 0.746831 0.395837 0.483043 0.046 Uiso calc U . R 1 . .
H H1B 0.808891 0.483641 0.562785 0.046 Uiso calc U . R 1 . .
H H1C 0.750712 0.534167 0.458686 0.046 Uiso calc U . R 1 . .
C C2 0.71043(12) 0.5171(2) 0.53269(17) 0.0221(6) Uani d . . . 1 . .
H H2A 0.723552 0.600839 0.558223 0.027 Uiso calc U . R 1 . .
H H2B 0.720092 0.462913 0.583163 0.027 Uiso calc U . R 1 . .
C C3 0.62024(15) 0.2898(2) 0.4814(2) 0.0297(6) Uani d . . . 1 . .
H H3A 0.601841 0.211417 0.449135 0.045 Uiso calc U . R 1 . .
H H3B 0.596072 0.311724 0.508741 0.045 Uiso calc U . R 1 . .
H H3C 0.672179 0.283572 0.531316 0.045 Uiso calc U . R 1 . .
C C4 0.60579(14) 0.3863(2) 0.41225(18) 0.0254(6) Uani d . . . 1 . .
H H4A 0.553403 0.388584 0.360725 0.031 Uiso calc U . R 1 . .
H H4B 0.629978 0.362273 0.384696 0.031 Uiso calc U . R 1 . .
C C5 0.63063(15) 0.7274(2) 0.3946(2) 0.0301(7) Uani d . . . 1 . .
H H5A 0.618531 0.770545 0.338964 0.045 Uiso calc U . R 1 . .
H H5B 0.68228 0.735457 0.445457 0.045 Uiso calc U . R 1 . .
H H5C 0.603377 0.762483 0.414343 0.045 Uiso calc U . R 1 . .
C C6 0.61156(14) 0.5938(2) 0.37130(17) 0.0243(6) Uani d . . . 1 . .
H H6A 0.559175 0.587241 0.320451 0.029 Uiso calc U . R 1 . .
H H6B 0.636541 0.561426 0.346746 0.029 Uiso calc U . R 1 . .
C C7 0.47331(15) 0.6580(3) 0.3931(2) 0.0392(7) Uani d . . . 1 . .
H H7A 0.495905 0.734983 0.416476 0.047 Uiso calc U . R 1 . .
H H7B 0.422425 0.65288 0.348685 0.047 Uiso calc U . R 1 . .
C C8 0.51234(14) 0.5587(3) 0.42223(19) 0.0282(6) Uani d . . . 1 . .
H H8 0.488352 0.482926 0.397725 0.034 Uiso calc U . R 1 . .
C C9 0.59217(12) 0.5584(2) 0.49154(17) 0.0211(6) Uani d . . . 1 . .
H H9A 0.606327 0.505873 0.545057 0.025 Uiso calc U . R 1 . .
H H9B 0.608695 0.642002 0.515834 0.025 Uiso calc U . R 1 . .
C C10 0.91632(15) 0.3710(4) 0.8245(2) 0.0468(9) Uani d . . . 1 . .
C C11 0.88073(15) 0.4832(3) 0.83102(19) 0.0364(7) Uani d . . . 1 . .
C C12 0.83638(14) 0.4591(2) 0.86618(18) 0.0259(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 . 1.425(2) ?
S1 O4 . 1.4264(19) ?
S1 N2 . 1.577(2) ?
S1 C10 . 1.833(4) ?
S2 O2 . 1.4280(19) ?
S2 O1 . 1.429(2) ?
S2 N2 . 1.574(2) ?
S2 C12 . 1.842(3) ?
F1 C10 . 1.344(3) ?
F2 C10 . 1.354(3) ?
F3 C11 . 1.351(3) ?
F4 C11 . 1.351(3) ?
F5 C12 . 1.342(3) ?
F6 C12 . 1.353(3) ?
N1 C6 . 1.518(3) ?
N1 C2 . 1.519(3) ?
N1 C4 . 1.519(3) ?
N1 C9 . 1.521(3) ?
C1 C2 . 1.512(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.508(4) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.518(4) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.310(4) ?
C7 H7A . 0.95 ?
C7 H7B . 0.95 ?
C8 C9 . 1.487(3) ?
C8 H8 . 0.95 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.533(5) ?
C11 C12 . 1.534(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O4 . . 117.57(12) ?
O3 S1 N2 . . 108.62(14) ?
O4 S1 N2 . . 116.66(12) ?
O3 S1 C10 . . 105.78(17) ?
O4 S1 C10 . . 105.17(14) ?
N2 S1 C10 . . 101.01(13) ?
O2 S2 O1 . . 118.77(12) ?
O2 S2 N2 . . 116.15(12) ?
O1 S2 N2 . . 107.98(12) ?
O2 S2 C12 . . 105.62(11) ?
O1 S2 C12 . . 105.46(12) ?
N2 S2 C12 . . 100.65(13) ?
C6 N1 C2 . . 111.57(19) ?
C6 N1 C4 . . 105.96(18) ?
C2 N1 C4 . . 111.40(19) ?
C6 N1 C9 . . 110.53(18) ?
C2 N1 C9 . . 106.59(18) ?
C4 N1 C9 . . 110.88(19) ?
S2 N2 S1 . . 120.01(14) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C1 C2 N1 . . 114.9(2) ?
C1 C2 H2A . . 108.6 ?
N1 C2 H2A . . 108.6 ?
C1 C2 H2B . . 108.6 ?
N1 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C3 C4 N1 . . 115.4(2) ?
C3 C4 H4A . . 108.4 ?
N1 C4 H4A . . 108.4 ?
C3 C4 H4B . . 108.4 ?
N1 C4 H4B . . 108.4 ?
H4A C4 H4B . . 107.5 ?
C6 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C6 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N1 C6 C5 . . 115.5(2) ?
N1 C6 H6A . . 108.4 ?
C5 C6 H6A . . 108.4 ?
N1 C6 H6B . . 108.4 ?
C5 C6 H6B . . 108.4 ?
H6A C6 H6B . . 107.5 ?
C8 C7 H7A . . 120.0 ?
C8 C7 H7B . . 120.0 ?
H7A C7 H7B . . 120.0 ?
C7 C8 C9 . . 123.5(3) ?
C7 C8 H8 . . 118.2 ?
C9 C8 H8 . . 118.2 ?
C8 C9 N1 . . 114.1(2) ?
C8 C9 H9A . . 108.7 ?
N1 C9 H9A . . 108.7 ?
C8 C9 H9B . . 108.7 ?
N1 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
F1 C10 F2 . . 108.1(2) ?
F1 C10 C11 . . 109.0(3) ?
F2 C10 C11 . . 107.7(3) ?
F1 C10 S1 . . 109.7(2) ?
F2 C10 S1 . . 108.4(3) ?
C11 C10 S1 . . 113.82(19) ?
F4 C11 F3 . . 107.3(2) ?
F4 C11 C10 . . 108.8(2) ?
F3 C11 C10 . . 108.6(2) ?
F4 C11 C12 . . 108.7(2) ?
F3 C11 C12 . . 107.5(2) ?
C10 C11 C12 . . 115.5(2) ?
F5 C12 F6 . . 107.6(2) ?
F5 C12 C11 . . 109.5(2) ?
F6 C12 C11 . . 108.4(2) ?
F5 C12 S2 . . 109.37(18) ?
F6 C12 S2 . . 108.37(17) ?
C11 C12 S2 . . 113.47(19) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S2 N2 S1 . . . . 47.2(2) ?
O1 S2 N2 S1 . . . . -176.45(15) ?
C12 S2 N2 S1 . . . . -66.19(18) ?
O3 S1 N2 S2 . . . . 176.87(17) ?
O4 S1 N2 S2 . . . . -47.4(2) ?
C10 S1 N2 S2 . . . . 65.90(19) ?
C6 N1 C2 C1 . . . . -57.5(3) ?
C4 N1 C2 C1 . . . . 60.7(3) ?
C9 N1 C2 C1 . . . . -178.2(2) ?
C6 N1 C4 C3 . . . . 179.1(2) ?
C2 N1 C4 C3 . . . . 57.6(3) ?
C9 N1 C4 C3 . . . . -60.9(3) ?
C2 N1 C6 C5 . . . . -59.2(3) ?
C4 N1 C6 C5 . . . . 179.4(2) ?
C9 N1 C6 C5 . . . . 59.2(3) ?
C7 C8 C9 N1 . . . . -115.1(3) ?
C6 N1 C9 C8 . . . . 59.8(3) ?
C2 N1 C9 C8 . . . . -178.8(2) ?
C4 N1 C9 C8 . . . . -57.4(3) ?
O3 S1 C10 F1 . . . . 72.9(2) ?
O4 S1 C10 F1 . . . . -52.2(2) ?
N2 S1 C10 F1 . . . . -173.9(2) ?
O3 S1 C10 F2 . . . . -44.9(2) ?
O4 S1 C10 F2 . . . . -169.99(18) ?
N2 S1 C10 F2 . . . . 68.2(2) ?
O3 S1 C10 C11 . . . . -164.7(2) ?
O4 S1 C10 C11 . . . . 70.2(2) ?
N2 S1 C10 C11 . . . . -51.6(2) ?
F1 C10 C11 F4 . . . . 51.7(3) ?
F2 C10 C11 F4 . . . . 168.8(2) ?
S1 C10 C11 F4 . . . . -71.0(3) ?
F1 C10 C11 F3 . . . . -64.8(3) ?
F2 C10 C11 F3 . . . . 52.2(3) ?
S1 C10 C11 F3 . . . . 172.43(19) ?
F1 C10 C11 C12 . . . . 174.3(2) ?
F2 C10 C11 C12 . . . . -68.6(3) ?
S1 C10 C11 C12 . . . . 51.6(3) ?
F4 C11 C12 F5 . . . . -51.8(3) ?
F3 C11 C12 F5 . . . . 64.1(3) ?
C10 C11 C12 F5 . . . . -174.4(2) ?
F4 C11 C12 F6 . . . . -168.9(2) ?
F3 C11 C12 F6 . . . . -53.0(3) ?
C10 C11 C12 F6 . . . . 68.5(3) ?
F4 C11 C12 S2 . . . . 70.7(3) ?
F3 C11 C12 S2 . . . . -173.36(19) ?
C10 C11 C12 S2 . . . . -51.9(3) ?
O2 S2 C12 F5 . . . . 53.8(2) ?
O1 S2 C12 F5 . . . . -72.8(2) ?
N2 S2 C12 F5 . . . . 174.97(18) ?
O2 S2 C12 F6 . . . . 170.80(16) ?
O1 S2 C12 F6 . . . . 44.2(2) ?
N2 S2 C12 F6 . . . . -67.98(19) ?
O2 S2 C12 C11 . . . . -68.8(2) ?
O1 S2 C12 C11 . . . . 164.6(2) ?
N2 S2 C12 C11 . . . . 52.4(2) ?

####################################################################### 
# 
# 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_1CPFSA_Br2_90K
_database_code_depnum_ccdc_archive 'CCDC 2256554'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Mochida'
;Kobe University
Japan
;
_audit_update_record             
;
2023-04-15 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            NMe3VCPFSA_Br2_CPFSA
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Br2 F6 N2 O4 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         538.14

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.144(13)
_cell_length_b                   7.460(3)
_cell_length_c                   16.328(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.839(5)
_cell_angle_gamma                90
_cell_volume                     3355.(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4873
_cell_measurement_theta_min      2.5000
_cell_measurement_theta_max      28.6306
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.016
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096

_exptl_absorpt_coefficient_mu    5.161
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9050
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3824
_reflns_number_gt                3093
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1006
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_number_reflns         3824
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    undef
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.2197P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.272
_refine_diff_density_min         -1.030
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'Generate Report (Bruker AXS Inc. , 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.59593(15) 0.5259(5) 0.4094(3) 0.0266(9) Uani d . . . 1 . .
H H1A 0.564642 0.463407 0.380175 0.04 Uiso calc U . R 1 . .
H H1B 0.621651 0.44094 0.446947 0.04 Uiso calc U . R 1 . .
H H1C 0.602746 0.577114 0.361416 0.04 Uiso calc U . R 1 . .
C C2 0.64244(15) 0.7660(5) 0.5132(3) 0.0261(8) Uani d . . . 1 . .
H H2A 0.646331 0.83258 0.46539 0.039 Uiso calc U . R 1 . .
H H2B 0.668265 0.676183 0.540888 0.039 Uiso calc U . R 1 . .
H H2C 0.64439 0.849156 0.561324 0.039 Uiso calc U . R 1 . .
C C3 0.58538(16) 0.5936(5) 0.5461(3) 0.0267(9) Uani d . . . 1 . .
H H3A 0.556351 0.517721 0.518471 0.04 Uiso calc U . R 1 . .
H H3B 0.58064 0.689573 0.582093 0.04 Uiso calc U . R 1 . .
H H3C 0.613517 0.520965 0.586939 0.04 Uiso calc U . R 1 . .
C C4 0.55468(14) 0.8098(4) 0.4108(2) 0.0192(7) Uani d . . . 1 . .
H H4 0.560763 0.845564 0.358122 0.023 Uiso calc U . R 1 . .
C C5 0.55649(14) 0.9775(4) 0.4645(2) 0.0206(7) Uani d . . . 1 . .
H H5A 0.589253 1.031574 0.490272 0.025 Uiso calc U . R 1 . .
H H5B 0.550098 0.946192 0.516699 0.025 Uiso calc U . R 1 . .
C C6 0.70828(14) -0.0653(5) 0.2829(3) 0.0239(8) Uani d . . . 1 . .
C C7 0.72039(14) 0.0754(5) 0.3605(3) 0.0267(8) Uani d . . . 1 . .
C C8 0.68600(14) 0.2391(5) 0.3330(3) 0.0239(8) Uani d . . . 1 . .
Br Br1 0.50858(2) 1.14842(5) 0.38446(3) 0.02348(12) Uani d . . . 1 . .
Br Br2 0.49093(2) 0.69685(5) 0.35923(3) 0.02553(12) Uani d . . . 1 . .
F F1 0.69846(10) 0.3419(3) 0.40860(17) 0.0373(6) Uani d . . . 1 . .
F F2 0.69239(9) 0.3359(3) 0.26984(17) 0.0306(6) Uani d . . . 1 . .
F F3 0.71955(9) -0.0070(3) 0.43325(14) 0.0345(6) Uani d . . . 1 . .
F F4 0.76610(9) 0.1337(3) 0.38771(18) 0.0400(6) Uani d . . . 1 . .
F F5 0.71812(9) 0.0078(3) 0.21792(16) 0.0303(5) Uani d . . . 1 . .
F F6 0.73784(9) -0.2071(3) 0.31956(17) 0.0352(6) Uani d . . . 1 . .
N N1 0.59402(12) 0.6743(4) 0.4706(2) 0.0182(6) Uani d . . . 1 . .
N N00G 0.61699(11) 0.0469(3) 0.20265(19) 0.0182(6) Uani d . . . 1 . .
O O1 0.59459(10) 0.3351(3) 0.24358(18) 0.0216(6) Uani d . . . 1 . .
O O2 0.61701(10) 0.0938(3) 0.35843(18) 0.0266(6) Uani d . . . 1 . .
O O3 0.63687(11) -0.2202(3) 0.14105(19) 0.0309(7) Uani d . . . 1 . .
O O4 0.63963(11) -0.2474(3) 0.2942(2) 0.0311(7) Uani d . . . 1 . .
S S1 0.62190(3) 0.17612(11) 0.28392(6) 0.01758(19) Uani d . . . 1 . .
S S2 0.64477(4) -0.13914(11) 0.22645(6) 0.0206(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.511(4) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.499(5) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 N1 . 1.505(4) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 C5 . 1.513(5) ?
C4 N1 . 1.536(5) ?
C4 Br2 . 1.949(4) ?
C4 H4 . 1.0 ?
C5 Br1 . 1.933(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 F6 . 1.345(4) ?
C6 F5 . 1.349(4) ?
C6 C7 . 1.550(5) ?
C6 S2 . 1.834(4) ?
C7 F3 . 1.349(4) ?
C7 F4 . 1.350(5) ?
C7 C8 . 1.546(5) ?
C8 F2 . 1.348(4) ?
C8 F1 . 1.348(4) ?
C8 S1 . 1.831(4) ?
N00G S2 . 1.585(3) ?
N00G S1 . 1.589(3) ?
O1 S1 . 1.429(3) ?
O2 S1 . 1.433(3) ?
O3 S2 . 1.432(3) ?
O4 S2 . 1.437(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C5 C4 N1 . . 111.9(3) ?
C5 C4 Br2 . . 111.3(3) ?
N1 C4 Br2 . . 109.8(2) ?
C5 C4 H4 . . 107.9 ?
N1 C4 H4 . . 107.9 ?
Br2 C4 H4 . . 107.9 ?
C4 C5 Br1 . . 110.2(2) ?
C4 C5 H5A . . 109.6 ?
Br1 C5 H5A . . 109.6 ?
C4 C5 H5B . . 109.6 ?
Br1 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
F6 C6 F5 . . 108.0(3) ?
F6 C6 C7 . . 108.3(3) ?
F5 C6 C7 . . 108.1(3) ?
F6 C6 S2 . . 109.9(2) ?
F5 C6 S2 . . 108.3(2) ?
C7 C6 S2 . . 114.1(3) ?
F3 C7 F4 . . 107.9(3) ?
F3 C7 C8 . . 108.6(3) ?
F4 C7 C8 . . 108.8(3) ?
F3 C7 C6 . . 108.3(3) ?
F4 C7 C6 . . 107.7(3) ?
C8 C7 C6 . . 115.2(3) ?
F2 C8 F1 . . 108.3(3) ?
F2 C8 C7 . . 108.4(3) ?
F1 C8 C7 . . 108.6(3) ?
F2 C8 S1 . . 108.9(3) ?
F1 C8 S1 . . 109.6(3) ?
C7 C8 S1 . . 113.0(3) ?
C2 N1 C3 . . 109.2(3) ?
C2 N1 C1 . . 107.4(3) ?
C3 N1 C1 . . 109.0(3) ?
C2 N1 C4 . . 109.0(3) ?
C3 N1 C4 . . 112.9(3) ?
C1 N1 C4 . . 109.1(3) ?
S2 N00G S1 . . 119.87(18) ?
O1 S1 O2 . . 118.09(16) ?
O1 S1 N00G . . 108.32(15) ?
O2 S1 N00G . . 116.23(16) ?
O1 S1 C8 . . 106.35(17) ?
O2 S1 C8 . . 105.36(17) ?
N00G S1 C8 . . 100.43(16) ?
O3 S2 O4 . . 118.79(17) ?
O3 S2 N00G . . 107.78(16) ?
O4 S2 N00G . . 115.87(17) ?
O3 S2 C6 . . 105.70(18) ?
O4 S2 C6 . . 105.29(17) ?
N00G S2 C6 . . 101.39(16) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C4 C5 Br1 . . . . 177.0(2) ?
Br2 C4 C5 Br1 . . . . -59.7(3) ?
F6 C6 C7 F3 . . . . -51.7(4) ?
F5 C6 C7 F3 . . . . -168.5(3) ?
S2 C6 C7 F3 . . . . 71.0(3) ?
F6 C6 C7 F4 . . . . 64.8(4) ?
F5 C6 C7 F4 . . . . -52.0(4) ?
S2 C6 C7 F4 . . . . -172.5(2) ?
F6 C6 C7 C8 . . . . -173.6(3) ?
F5 C6 C7 C8 . . . . 69.6(4) ?
S2 C6 C7 C8 . . . . -50.9(4) ?
F3 C7 C8 F2 . . . . 170.9(3) ?
F4 C7 C8 F2 . . . . 53.7(4) ?
C6 C7 C8 F2 . . . . -67.4(4) ?
F3 C7 C8 F1 . . . . 53.5(4) ?
F4 C7 C8 F1 . . . . -63.8(4) ?
C6 C7 C8 F1 . . . . 175.2(3) ?
F3 C7 C8 S1 . . . . -68.4(3) ?
F4 C7 C8 S1 . . . . 174.4(2) ?
C6 C7 C8 S1 . . . . 53.4(4) ?
C5 C4 N1 C2 . . . . -53.2(4) ?
Br2 C4 N1 C2 . . . . -177.3(2) ?
C5 C4 N1 C3 . . . . 68.3(4) ?
Br2 C4 N1 C3 . . . . -55.8(3) ?
C5 C4 N1 C1 . . . . -170.3(3) ?
Br2 C4 N1 C1 . . . . 65.6(3) ?
S2 N00G S1 O1 . . . . 178.4(2) ?
S2 N00G S1 O2 . . . . -45.9(3) ?
S2 N00G S1 C8 . . . . 67.1(2) ?
F2 C8 S1 O1 . . . . -47.0(3) ?
F1 C8 S1 O1 . . . . 71.3(3) ?
C7 C8 S1 O1 . . . . -167.4(3) ?
F2 C8 S1 O2 . . . . -173.1(2) ?
F1 C8 S1 O2 . . . . -54.8(3) ?
C7 C8 S1 O2 . . . . 66.5(3) ?
F2 C8 S1 N00G . . . . 65.8(3) ?
F1 C8 S1 N00G . . . . -175.9(2) ?
C7 C8 S1 N00G . . . . -54.6(3) ?
S1 N00G S2 O3 . . . . -175.7(2) ?
S1 N00G S2 O4 . . . . 48.5(3) ?
S1 N00G S2 C6 . . . . -64.9(2) ?
F6 C6 S2 O3 . . . . -75.9(3) ?
F5 C6 S2 O3 . . . . 41.8(3) ?
C7 C6 S2 O3 . . . . 162.3(3) ?
F6 C6 S2 O4 . . . . 50.6(3) ?
F5 C6 S2 O4 . . . . 168.4(2) ?
C7 C6 S2 O4 . . . . -71.2(3) ?
F6 C6 S2 N00G . . . . 171.7(2) ?
F5 C6 S2 N00G . . . . -70.5(3) ?
C7 C6 S2 N00G . . . . 49.9(3) ?

