# 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 2020

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2023800'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C21 H17 F6 N O4 S'
_chemical_formula_sum            'C21 H17 F6 N O4 S'
_chemical_formula_weight         493.42

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'
F F 0.0171 0.0103 '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'

_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                   11.8375(3)
_cell_length_b                   15.1552(4)
_cell_length_c                   10.8340(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.296(2)
_cell_angle_gamma                90
_cell_volume                     1912.32(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6945
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      30.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18621
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.135
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5544
_reflns_number_gt                4668
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0435P)²+0.8135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         5544
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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 0.23756(3) 0.68604(2) 0.38472(3) 0.01381(8) Uani 1 1 d . . . . .
F1 F 0.54543(8) 0.32162(6) 0.80006(9) 0.0287(2) Uani 1 1 d . . . . .
F2 F 0.37495(8) 0.26845(5) 0.77442(8) 0.02490(19) Uani 1 1 d . . . . .
F3 F 0.42274(7) 0.37402(5) 0.90473(7) 0.02117(17) Uani 1 1 d . . . . .
F4 F 0.11457(7) 0.50298(6) 0.72807(8) 0.02477(19) Uani 1 1 d . . . . .
F5 F 0.25396(7) 0.50879(6) 0.88358(7) 0.02104(17) Uani 1 1 d . . . . .
F6 F 0.19652(7) 0.38372(5) 0.80444(8) 0.02090(17) Uani 1 1 d . . . . .
O1 O 0.33732(8) 0.74019(6) 0.41993(9) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.22204(8) 0.63577(6) 0.27078(9) 0.01842(19) Uani 1 1 d . . . . .
O10 O 0.32552(8) 0.43911(6) 0.47692(8) 0.01442(17) Uani 1 1 d . . . . .
O11 O 0.44874(7) 0.55042(6) 0.61459(8) 0.01413(17) Uani 1 1 d . . . . .
N2 N 0.23696(9) 0.61662(7) 0.49864(10) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.16567(11) 0.53712(8) 0.47987(12) 0.0152(2) Uani 1 1 d . . . . .
H1A H 0.141380 0.525887 0.388982 0.018 Uiso 1 1 calc R U . . .
H1B H 0.095917 0.545697 0.517068 0.018 Uiso 1 1 calc R U . . .
C3 C 0.28488(11) 0.64203(8) 0.62836(12) 0.0149(2) Uani 1 1 d . . . . .
H3A H 0.222153 0.651678 0.676288 0.018 Uiso 1 1 calc R U . . .
H3B H 0.329067 0.697543 0.629026 0.018 Uiso 1 1 calc R U . . .
C3A C 0.36234(10) 0.56869(8) 0.68736(11) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.43545(11) 0.57984(8) 0.81758(12) 0.0163(2) Uani 1 1 d . . . . .
H4A H 0.421630 0.618125 0.882713 0.020 Uiso 1 1 calc R U . . .
C5 C 0.52256(11) 0.52434(9) 0.81987(12) 0.0175(2) Uani 1 1 d . . . . .
H5A H 0.583793 0.513929 0.887887 0.021 Uiso 1 1 calc R U . . .
C6A C 0.40323(10) 0.41113(8) 0.68557(11) 0.0129(2) Uani 1 1 d . . . . .
C6 C 0.50422(11) 0.48068(8) 0.69090(12) 0.0152(2) Uani 1 1 d . . . . .
H6A H 0.575433 0.457343 0.664883 0.018 Uiso 1 1 calc R U . . .
C7 C 0.37066(12) 0.36555(8) 0.55234(12) 0.0157(2) Uani 1 1 d . . . . .
H7A H 0.435259 0.334003 0.523139 0.019 Uiso 1 1 calc R U . . .
C8 C 0.26240(12) 0.31100(9) 0.54892(12) 0.0184(3) Uani 1 1 d . . . . .
H8A H 0.257181 0.248510 0.551934 0.022 Uiso 1 1 calc R U . . .
C9A C 0.23310(10) 0.45887(8) 0.54105(11) 0.0127(2) Uani 1 1 d . . . . .
C9B C 0.29945(10) 0.47584(8) 0.68087(11) 0.0118(2) Uani 1 1 d . . . . .
C9 C 0.17659(12) 0.36834(8) 0.54088(12) 0.0168(2) Uani 1 1 d . . . . .
H9A H 0.097301 0.355766 0.536061 0.020 Uiso 1 1 calc R U . . .
C10 C 0.43464(11) 0.34391(9) 0.79112(12) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.21801(11) 0.46711(8) 0.77475(12) 0.0152(2) Uani 1 1 d . . . . .
C12 C 0.11622(11) 0.75468(8) 0.37690(11) 0.0134(2) Uani 1 1 d . . . . .
C13 C 0.11333(12) 0.81840(8) 0.46932(12) 0.0169(2) Uani 1 1 d . . . . .
H13A H 0.176491 0.825402 0.536271 0.020 Uiso 1 1 calc R U . . .
C14 C 0.01681(12) 0.87131(9) 0.46185(12) 0.0183(3) Uani 1 1 d . . . . .
H14A H 0.014015 0.914256 0.525103 0.022 Uiso 1 1 calc R U . . .
C15 C -0.07638(11) 0.86288(8) 0.36345(12) 0.0158(2) Uani 1 1 d . . . . .
C16 C -0.07135(11) 0.79860(9) 0.27285(12) 0.0171(2) Uani 1 1 d . . . . .
H16A H -0.134329 0.791659 0.205688 0.021 Uiso 1 1 calc R U . . .
C17 C 0.02411(11) 0.74443(8) 0.27890(12) 0.0159(2) Uani 1 1 d . . . . .
H17A H 0.026341 0.700738 0.216500 0.019 Uiso 1 1 calc R U . . .
C18 C -0.18057(12) 0.92076(9) 0.35508(13) 0.0216(3) Uani 1 1 d . . . . .
H18A H -0.157973 0.982698 0.350268 0.032 Uiso 1 1 calc R U . . .
H18B H -0.215478 0.911973 0.429645 0.032 Uiso 1 1 calc R U . . .
H18C H -0.236207 0.905349 0.279868 0.032 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 1.4326(10) . ?
S1 O2 1.4342(10) . ?
S1 N2 1.6228(11) . ?
S1 C12 1.7633(13) . ?
F1 C10 1.3410(15) . ?
F2 C10 1.3395(16) . ?
F3 C10 1.3434(15) . ?
F4 C11 1.3526(15) . ?
F5 C11 1.3383(15) . ?
F6 C11 1.3396(15) . ?
O10 C7 1.4282(15) . ?
O10 C9A 1.4286(15) . ?
O11 C3A 1.4257(15) . ?
O11 C6 1.4276(15) . ?
N2 C1 1.4641(16) . ?
N2 C3 1.4698(16) . ?
C1 C9A 1.5145(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C3A 1.5084(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.5270(17) . ?
C3A C9B 1.5876(17) . ?
C4 C5 1.3275(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.5261(18) . ?
C5 H5A 0.9500 . ?
C6A C10 1.5270(17) . ?
C6A C9B 1.5657(17) . ?
C6A C7 1.5843(17) . ?
C6A C6 1.5871(18) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5200(19) . ?
C7 H7A 1.0000 . ?
C8 C9 1.3278(19) . ?
C8 H8A 0.9500 . ?
C9A C9 1.5262(17) . ?
C9A C9B 1.5976(17) . ?
C9B C11 1.5271(17) . ?
C9 H9A 0.9500 . ?
C12 C17 1.3880(17) . ?
C12 C13 1.3959(17) . ?
C13 C14 1.3862(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3962(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3916(18) . ?
C15 C18 1.5030(18) . ?
C16 C17 1.3888(18) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 O2 120.41(6) . . ?
O1 S1 N2 106.52(6) . . ?
O2 S1 N2 107.03(6) . . ?
O1 S1 C12 107.48(6) . . ?
O2 S1 C12 107.11(6) . . ?
N2 S1 C12 107.74(6) . . ?
C7 O10 C9A 97.25(9) . . ?
C3A O11 C6 97.17(9) . . ?
C1 N2 C3 117.57(10) . . ?
C1 N2 S1 120.58(8) . . ?
C3 N2 S1 120.26(8) . . ?
N2 C1 C9A 109.75(10) . . ?
N2 C1 H1A 109.7 . . ?
C9A C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C9A C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C3 C3A 108.27(10) . . ?
N2 C3 H3A 110.0 . . ?
C3A C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C3A C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O11 C3A C3 110.53(10) . . ?
O11 C3A C4 100.85(10) . . ?
C3 C3A C4 120.74(10) . . ?
O11 C3A C9B 100.40(9) . . ?
C3 C3A C9B 112.93(10) . . ?
C4 C3A C9B 108.84(10) . . ?
C5 C4 C3A 104.90(11) . . ?
C5 C4 H4A 127.5 . . ?
C3A C4 H4A 127.5 . . ?
C4 C5 C6 105.95(11) . . ?
C4 C5 H5A 127.0 . . ?
C6 C5 H5A 127.0 . . ?
C10 C6A C9B 121.79(10) . . ?
C10 C6A C7 112.24(10) . . ?
C9B C6A C7 100.47(9) . . ?
C10 C6A C6 109.56(10) . . ?
C9B C6A C6 99.60(9) . . ?
C7 C6A C6 112.44(10) . . ?
O11 C6 C5 100.64(10) . . ?
O11 C6 C6A 101.83(9) . . ?
C5 C6 C6A 107.71(10) . . ?
O11 C6 H6A 115.0 . . ?
C5 C6 H6A 115.0 . . ?
C6A C6 H6A 115.0 . . ?
O10 C7 C8 100.54(10) . . ?
O10 C7 C6A 100.73(9) . . ?
C8 C7 C6A 109.04(10) . . ?
O10 C7 H7A 114.9 . . ?
C8 C7 H7A 114.9 . . ?
C6A C7 H7A 114.9 . . ?
C9 C8 C7 106.10(11) . . ?
C9 C8 H8A 126.9 . . ?
C7 C8 H8A 126.9 . . ?
O10 C9A C1 109.93(10) . . ?
O10 C9A C9 100.63(10) . . ?
C1 C9A C9 120.45(10) . . ?
O10 C9A C9B 101.85(9) . . ?
C1 C9A C9B 114.85(10) . . ?
C9 C9A C9B 106.68(9) . . ?
C11 C9B C6A 120.61(10) . . ?
C11 C9B C3A 113.21(10) . . ?
C6A C9B C3A 101.23(9) . . ?
C11 C9B C9A 110.83(10) . . ?
C6A C9B C9A 100.36(9) . . ?
C3A C9B C9A 109.38(9) . . ?
C8 C9 C9A 104.97(11) . . ?
C8 C9 H9A 127.5 . . ?
C9A C9 H9A 127.5 . . ?
F2 C10 F1 106.27(11) . . ?
F2 C10 F3 105.94(10) . . ?
F1 C10 F3 106.30(11) . . ?
F2 C10 C6A 114.61(11) . . ?
F1 C10 C6A 109.04(10) . . ?
F3 C10 C6A 114.09(10) . . ?
F5 C11 F6 106.14(10) . . ?
F5 C11 F4 105.29(10) . . ?
F6 C11 F4 105.72(10) . . ?
F5 C11 C9B 114.00(10) . . ?
F6 C11 C9B 114.28(10) . . ?
F4 C11 C9B 110.68(10) . . ?
C17 C12 C13 120.63(12) . . ?
C17 C12 S1 119.50(10) . . ?
C13 C12 S1 119.86(10) . . ?
C14 C13 C12 118.94(12) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C15 121.48(12) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C16 C15 C14 118.36(12) . . ?
C16 C15 C18 120.27(12) . . ?
C14 C15 C18 121.37(12) . . ?
C17 C16 C15 121.17(12) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C12 C17 C16 119.42(12) . . ?
C12 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 S1 N2 C1 -163.37(10) . . . . ?
O2 S1 N2 C1 -33.35(11) . . . . ?
C12 S1 N2 C1 81.55(11) . . . . ?
O1 S1 N2 C3 31.39(11) . . . . ?
O2 S1 N2 C3 161.41(10) . . . . ?
C12 S1 N2 C3 -83.69(11) . . . . ?
C3 N2 C1 C9A -57.13(14) . . . . ?
S1 N2 C1 C9A 137.25(9) . . . . ?
C1 N2 C3 C3A 61.55(14) . . . . ?
S1 N2 C3 C3A -132.78(10) . . . . ?
C6 O11 C3A C3 -179.34(10) . . . . ?
C6 O11 C3A C4 51.79(10) . . . . ?
C6 O11 C3A C9B -59.89(10) . . . . ?
N2 C3 C3A O11 56.01(13) . . . . ?
N2 C3 C3A C4 173.17(11) . . . . ?
N2 C3 C3A C9B -55.56(13) . . . . ?
O11 C3A C4 C5 -33.35(12) . . . . ?
C3 C3A C4 C5 -155.32(12) . . . . ?
C9B C3A C4 C5 71.69(13) . . . . ?
C3A C4 C5 C6 1.05(13) . . . . ?
C3A O11 C6 C5 -50.91(10) . . . . ?
C3A O11 C6 C6A 59.92(10) . . . . ?
C4 C5 C6 O11 31.46(13) . . . . ?
C4 C5 C6 C6A -74.75(13) . . . . ?
C10 C6A C6 O11 -163.48(10) . . . . ?
C9B C6A C6 O11 -34.65(11) . . . . ?
C7 C6A C6 O11 70.97(12) . . . . ?
C10 C6A C6 C5 -58.12(13) . . . . ?
C9B C6A C6 C5 70.71(11) . . . . ?
C7 C6A C6 C5 176.33(10) . . . . ?
C9A O10 C7 C8 51.07(10) . . . . ?
C9A O10 C7 C6A -60.83(10) . . . . ?
C10 C6A C7 O10 169.71(10) . . . . ?
C9B C6A C7 O10 38.84(11) . . . . ?
C6 C6A C7 O10 -66.21(12) . . . . ?
C10 C6A C7 C8 64.50(13) . . . . ?
C9B C6A C7 C8 -66.37(11) . . . . ?
C6 C6A C7 C8 -171.43(10) . . . . ?
O10 C7 C8 C9 -31.79(13) . . . . ?
C6A C7 C8 C9 73.55(13) . . . . ?
C7 O10 C9A C1 -179.70(10) . . . . ?
C7 O10 C9A C9 -51.64(10) . . . . ?
C7 O10 C9A C9B 58.10(10) . . . . ?
N2 C1 C9A O10 -66.87(12) . . . . ?
N2 C1 C9A C9 176.98(11) . . . . ?
N2 C1 C9A C9B 47.25(14) . . . . ?
C10 C6A C9B C11 -6.62(17) . . . . ?
C7 C6A C9B C11 117.95(11) . . . . ?
C6 C6A C9B C11 -126.90(11) . . . . ?
C10 C6A C9B C3A 119.14(12) . . . . ?
C7 C6A C9B C3A -116.29(9) . . . . ?
C6 C6A C9B C3A -1.14(10) . . . . ?
C10 C6A C9B C9A -128.51(11) . . . . ?
C7 C6A C9B C9A -3.94(11) . . . . ?
C6 C6A C9B C9A 111.21(9) . . . . ?
O11 C3A C9B C11 167.08(9) . . . . ?
C3 C3A C9B C11 -75.23(13) . . . . ?
C4 C3A C9B C11 61.72(13) . . . . ?
O11 C3A C9B C6A 36.54(10) . . . . ?
C3 C3A C9B C6A 154.23(10) . . . . ?
C4 C3A C9B C6A -68.82(11) . . . . ?
O11 C3A C9B C9A -68.79(11) . . . . ?
C3 C3A C9B C9A 48.90(13) . . . . ?
C4 C3A C9B C9A -174.14(10) . . . . ?
O10 C9A C9B C11 -160.49(9) . . . . ?
C1 C9A C9B C11 80.76(13) . . . . ?
C9 C9A C9B C11 -55.44(13) . . . . ?
O10 C9A C9B C6A -31.92(10) . . . . ?
C1 C9A C9B C6A -150.67(10) . . . . ?
C9 C9A C9B C6A 73.13(11) . . . . ?
O10 C9A C9B C3A 73.99(11) . . . . ?
C1 C9A C9B C3A -44.76(13) . . . . ?
C9 C9A C9B C3A 179.05(10) . . . . ?
C7 C8 C9 C9A -0.70(13) . . . . ?
O10 C9A C9 C8 33.00(12) . . . . ?
C1 C9A C9 C8 153.84(12) . . . . ?
C9B C9A C9 C8 -72.93(12) . . . . ?
C9B C6A C10 F2 84.00(14) . . . . ?
C7 C6A C10 F2 -34.97(15) . . . . ?
C6 C6A C10 F2 -160.64(10) . . . . ?
C9B C6A C10 F1 -157.05(11) . . . . ?
C7 C6A C10 F1 83.97(13) . . . . ?
C6 C6A C10 F1 -41.69(14) . . . . ?
C9B C6A C10 F3 -38.39(16) . . . . ?
C7 C6A C10 F3 -157.36(11) . . . . ?
C6 C6A C10 F3 76.97(13) . . . . ?
C6A C9B C11 F5 85.32(14) . . . . ?
C3A C9B C11 F5 -34.67(14) . . . . ?
C9A C9B C11 F5 -158.01(10) . . . . ?
C6A C9B C11 F6 -37.00(15) . . . . ?
C3A C9B C11 F6 -156.99(10) . . . . ?
C9A C9B C11 F6 79.67(13) . . . . ?
C6A C9B C11 F4 -156.21(11) . . . . ?
C3A C9B C11 F4 83.80(12) . . . . ?
C9A C9B C11 F4 -39.54(13) . . . . ?
O1 S1 C12 C17 138.04(10) . . . . ?
O2 S1 C12 C17 7.33(12) . . . . ?
N2 S1 C12 C17 -107.52(11) . . . . ?
O1 S1 C12 C13 -42.26(12) . . . . ?
O2 S1 C12 C13 -172.97(10) . . . . ?
N2 S1 C12 C13 72.18(11) . . . . ?
C17 C12 C13 C14 0.10(19) . . . . ?
S1 C12 C13 C14 -179.59(10) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C13 C14 C15 C18 -179.56(13) . . . . ?
C14 C15 C16 C17 -0.56(19) . . . . ?
C18 C15 C16 C17 -179.97(12) . . . . ?
C13 C12 C17 C16 0.35(19) . . . . ?
S1 C12 C17 C16 -179.95(10) . . . . ?
C15 C16 C17 C12 -0.1(2) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.059


# start Validation Reply Form
_vrf_PLAT910_6a                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 16 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 2023802'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C20 H14 F7 N O4 S'
_chemical_formula_sum            'C20 H14 F7 N O4 S'
_chemical_formula_weight         497.38

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'
F F 0.0171 0.0103 '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'

_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                   12.3306(4)
_cell_length_b                   10.6264(3)
_cell_length_c                   15.1459(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.930(1)
_cell_angle_gamma                90
_cell_volume                     1954.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31844
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.835
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5677
_reflns_number_gt                4082
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0563P)²+0.5217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         5677
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.72434(4) 0.25541(4) 0.58957(3) 0.04730(13) Uani 1 1 d . . . . .
F1 F 0.95120(11) 0.44704(17) 0.31044(9) 0.0905(5) Uani 1 1 d . . . . .
F2 F 0.80767(10) 0.68961(12) 0.65211(8) 0.0646(3) Uani 1 1 d . . . . .
F3 F 0.73843(10) 0.82153(9) 0.73184(10) 0.0696(4) Uani 1 1 d . . . . .
F4 F 0.88951(10) 0.73206(13) 0.78312(9) 0.0725(4) Uani 1 1 d . . . . .
F5 F 0.78576(10) 0.78391(12) 0.93013(9) 0.0702(4) Uani 1 1 d . . . . .
F6 F 0.62195(10) 0.83637(10) 0.87584(8) 0.0667(3) Uani 1 1 d . . . . .
F7 F 0.65190(14) 0.71434(14) 0.98861(8) 0.0837(4) Uani 1 1 d . . . . .
O1 O 0.73125(11) 0.41385(10) 0.84477(7) 0.0475(3) Uani 1 1 d . . . . .
O2 O 0.55824(9) 0.49716(10) 0.74988(7) 0.0393(3) Uani 1 1 d . . . . .
O3 O 0.79084(15) 0.16049(12) 0.63879(10) 0.0715(4) Uani 1 1 d . . . . .
O4 O 0.61343(12) 0.22875(13) 0.54911(10) 0.0640(4) Uani 1 1 d . . . . .
N2 N 0.71874(11) 0.37392(12) 0.65863(8) 0.0399(3) Uani 1 1 d . . . . .
C1 C 0.64881(13) 0.48036(15) 0.62153(10) 0.0390(3) Uani 1 1 d . . . . .
H1A H 0.580686 0.448688 0.587012 0.047 Uiso 1 1 calc R U . . .
H1B H 0.686351 0.528862 0.581666 0.047 Uiso 1 1 calc R U . . .
C3B C 0.72694(11) 0.60372(12) 0.76856(9) 0.0302(3) Uani 1 1 d . . . . .
C3 C 0.82353(14) 0.40652(16) 0.71712(11) 0.0434(4) Uani 1 1 d . . . . .
H3A H 0.869406 0.454702 0.683495 0.052 Uiso 1 1 calc R U . . .
H3B H 0.862768 0.330258 0.738396 0.052 Uiso 1 1 calc R U . . .
C3A C 0.80040(13) 0.48263(14) 0.79561(10) 0.0385(3) Uani 1 1 d . . . . .
C4 C 0.89412(17) 0.51841(19) 0.87032(13) 0.0578(5) Uani 1 1 d . . . . .
H4 H 0.968266 0.527105 0.866677 0.069 Uiso 1 1 calc R U . . .
C5 C 0.8473(2) 0.5344(2) 0.94142(13) 0.0666(6) Uani 1 1 d . . . . .
H5 H 0.881816 0.557786 0.998549 0.080 Uiso 1 1 calc R U . . .
C6A C 0.67128(13) 0.62141(14) 0.85302(9) 0.0358(3) Uani 1 1 d . . . . .
C6 C 0.72665(18) 0.50731(17) 0.91176(11) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.687820 0.481126 0.959970 0.063 Uiso 1 1 calc R U . . .
C7 C 0.54661(13) 0.59777(15) 0.81008(11) 0.0405(3) Uani 1 1 d . . . . .
H7 H 0.498156 0.579369 0.853375 0.049 Uiso 1 1 calc R U . . .
C8 C 0.50631(14) 0.70172(16) 0.74425(12) 0.0446(4) Uani 1 1 d . . . . .
H8 H 0.458696 0.767015 0.752175 0.054 Uiso 1 1 calc R U . . .
C9A C 0.62337(11) 0.56409(13) 0.69601(9) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.55269(13) 0.68067(15) 0.67315(11) 0.0408(3) Uani 1 1 d . . . . .
H9 H 0.543932 0.727268 0.620424 0.049 Uiso 1 1 calc R U . . .
C10 C 0.79016(13) 0.71237(15) 0.73538(11) 0.0405(3) Uani 1 1 d . . . . .
C11 C 0.68359(16) 0.74079(17) 0.90996(11) 0.0480(4) Uani 1 1 d . . . . .
C12 C 0.79362(13) 0.31109(14) 0.50520(10) 0.0375(3) Uani 1 1 d . . . . .
C13 C 0.90771(15) 0.3043(2) 0.51675(13) 0.0555(5) Uani 1 1 d . . . . .
H13 H 0.947820 0.268925 0.568428 0.067 Uiso 1 1 calc R U . . .
C14 C 0.96066(16) 0.3507(2) 0.45046(15) 0.0662(6) Uani 1 1 d . . . . .
H14 H 1.036999 0.347670 0.456881 0.079 Uiso 1 1 calc R U . . .
C15 C 0.89894(15) 0.4012(2) 0.37519(13) 0.0545(5) Uani 1 1 d . . . . .
C16 C 0.78708(15) 0.40882(17) 0.36241(12) 0.0466(4) Uani 1 1 d . . . . .
H16 H 0.747649 0.443890 0.310348 0.056 Uiso 1 1 calc R U . . .
C17 C 0.73380(13) 0.36318(16) 0.42862(11) 0.0408(3) Uani 1 1 d . . . . .
H17 H 0.657469 0.367515 0.421638 0.049 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 O3 1.4264(16) . ?
S1 O4 1.4273(15) . ?
S1 N2 1.6460(13) . ?
S1 C12 1.7577(16) . ?
F1 C15 1.353(2) . ?
F2 C10 1.338(2) . ?
F3 C10 1.3204(19) . ?
F4 C10 1.3274(19) . ?
F5 C11 1.326(2) . ?
F6 C11 1.319(2) . ?
F7 C11 1.346(2) . ?
O1 C3A 1.426(2) . ?
O1 C6 1.428(2) . ?
O2 C7 1.4283(17) . ?
O2 C9A 1.4291(17) . ?
N2 C1 1.474(2) . ?
N2 C3 1.476(2) . ?
C1 C9A 1.5115(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3B C10 1.526(2) . ?
C3B C6A 1.5639(19) . ?
C3B C3A 1.5863(19) . ?
C3B C9A 1.5912(19) . ?
C3 C3A 1.505(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.520(2) . ?
C4 C5 1.318(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.505(3) . ?
C5 H5 0.9300 . ?
C6A C11 1.527(2) . ?
C6A C7 1.583(2) . ?
C6A C6 1.587(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.513(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.323(2) . ?
C8 H8 0.9300 . ?
C9A C9 1.520(2) . ?
C9 H9 0.9300 . ?
C12 C17 1.379(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 H17 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
O3 S1 O4 120.39(10) . . ?
O3 S1 N2 107.00(8) . . ?
O4 S1 N2 106.41(8) . . ?
O3 S1 C12 108.08(9) . . ?
O4 S1 C12 107.73(8) . . ?
N2 S1 C12 106.46(7) . . ?
C3A O1 C6 96.61(12) . . ?
C7 O2 C9A 96.90(10) . . ?
C1 N2 C3 116.27(12) . . ?
C1 N2 S1 115.53(10) . . ?
C3 N2 S1 115.63(10) . . ?
N2 C1 C9A 110.52(12) . . ?
N2 C1 H1A 109.5 . . ?
C9A C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
C9A C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C10 C3B C6A 119.98(12) . . ?
C10 C3B C3A 113.42(12) . . ?
C6A C3B C3A 101.41(11) . . ?
C10 C3B C9A 111.57(11) . . ?
C6A C3B C9A 100.57(11) . . ?
C3A C3B C9A 108.56(11) . . ?
N2 C3 C3A 109.55(13) . . ?
N2 C3 H3A 109.8 . . ?
C3A C3 H3A 109.8 . . ?
N2 C3 H3B 109.8 . . ?
C3A C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O1 C3A C3 110.41(13) . . ?
O1 C3A C4 100.70(14) . . ?
C3 C3A C4 119.95(14) . . ?
O1 C3A C3B 100.62(11) . . ?
C3 C3A C3B 114.17(12) . . ?
C4 C3A C3B 108.44(13) . . ?
C5 C4 C3A 104.86(18) . . ?
C5 C4 H4 127.6 . . ?
C3A C4 H4 127.6 . . ?
C4 C5 C6 106.34(16) . . ?
C4 C5 H5 126.8 . . ?
C6 C5 H5 126.8 . . ?
C11 C6A C3B 123.16(13) . . ?
C11 C6A C7 111.04(13) . . ?
C3B C6A C7 100.19(11) . . ?
C11 C6A C6 109.08(12) . . ?
C3B C6A C6 99.19(12) . . ?
C7 C6A C6 113.74(14) . . ?
O1 C6 C5 100.77(15) . . ?
O1 C6 C6A 101.48(12) . . ?
C5 C6 C6A 109.18(16) . . ?
O1 C6 H6 114.6 . . ?
C5 C6 H6 114.6 . . ?
C6A C6 H6 114.6 . . ?
O2 C7 C8 100.58(12) . . ?
O2 C7 C6A 100.59(11) . . ?
C8 C7 C6A 109.89(13) . . ?
O2 C7 H7 114.7 . . ?
C8 C7 H7 114.7 . . ?
C6A C7 H7 114.7 . . ?
C9 C8 C7 105.90(14) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
O2 C9A C1 110.03(12) . . ?
O2 C9A C9 100.32(11) . . ?
C1 C9A C9 119.64(12) . . ?
O2 C9A C3B 101.57(10) . . ?
C1 C9A C3B 115.21(12) . . ?
C9 C9A C3B 107.58(11) . . ?
C8 C9 C9A 105.30(14) . . ?
C8 C9 H9 127.4 . . ?
C9A C9 H9 127.4 . . ?
F3 C10 F4 106.12(14) . . ?
F3 C10 F2 106.01(14) . . ?
F4 C10 F2 104.96(14) . . ?
F3 C10 C3B 114.05(13) . . ?
F4 C10 C3B 114.57(13) . . ?
F2 C10 C3B 110.39(13) . . ?
F6 C11 F5 106.53(15) . . ?
F6 C11 F7 105.78(15) . . ?
F5 C11 F7 106.12(15) . . ?
F6 C11 C6A 115.08(14) . . ?
F5 C11 C6A 114.54(14) . . ?
F7 C11 C6A 108.10(15) . . ?
C17 C12 C13 120.67(15) . . ?
C17 C12 S1 119.35(12) . . ?
C13 C12 S1 119.97(13) . . ?
C14 C13 C12 119.06(17) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 118.82(17) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
F1 C15 C16 118.22(18) . . ?
F1 C15 C14 118.65(17) . . ?
C16 C15 C14 123.13(17) . . ?
C15 C16 C17 118.29(17) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 120.03(15) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?

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
O3 S1 N2 C1 -177.17(12) . . . . ?
O4 S1 N2 C1 -47.26(13) . . . . ?
C12 S1 N2 C1 67.45(13) . . . . ?
O3 S1 N2 C3 42.19(14) . . . . ?
O4 S1 N2 C3 172.10(12) . . . . ?
C12 S1 N2 C3 -73.19(13) . . . . ?
C3 N2 C1 C9A -56.11(17) . . . . ?
S1 N2 C1 C9A 163.51(10) . . . . ?
C1 N2 C3 C3A 58.81(17) . . . . ?
S1 N2 C3 C3A -160.85(11) . . . . ?
C6 O1 C3A C3 179.37(13) . . . . ?
C6 O1 C3A C4 51.60(14) . . . . ?
C6 O1 C3A C3B -59.69(13) . . . . ?
N2 C3 C3A O1 58.32(16) . . . . ?
N2 C3 C3A C4 174.62(15) . . . . ?
N2 C3 C3A C3B -54.17(18) . . . . ?
C10 C3B C3A O1 165.12(12) . . . . ?
C6A C3B C3A O1 35.12(13) . . . . ?
C9A C3B C3A O1 -70.26(13) . . . . ?
C10 C3B C3A C3 -76.65(17) . . . . ?
C6A C3B C3A C3 153.35(13) . . . . ?
C9A C3B C3A C3 47.97(17) . . . . ?
C10 C3B C3A C4 59.95(17) . . . . ?
C6A C3B C3A C4 -70.06(16) . . . . ?
C9A C3B C3A C4 -175.43(13) . . . . ?
O1 C3A C4 C5 -33.29(18) . . . . ?
C3 C3A C4 C5 -154.53(17) . . . . ?
C3B C3A C4 C5 71.82(19) . . . . ?
C3A C4 C5 C6 0.7(2) . . . . ?
C10 C3B C6A C11 -4.7(2) . . . . ?
C3A C3B C6A C11 121.05(15) . . . . ?
C9A C3B C6A C11 -127.36(14) . . . . ?
C10 C3B C6A C7 118.86(14) . . . . ?
C3A C3B C6A C7 -115.37(12) . . . . ?
C9A C3B C6A C7 -3.78(13) . . . . ?
C10 C3B C6A C6 -124.81(14) . . . . ?
C3A C3B C6A C6 0.96(14) . . . . ?
C9A C3B C6A C6 112.54(12) . . . . ?
C3A O1 C6 C5 -51.12(14) . . . . ?
C3A O1 C6 C6A 61.20(15) . . . . ?
C4 C5 C6 O1 31.99(19) . . . . ?
C4 C5 C6 C6A -74.31(19) . . . . ?
C11 C6A C6 O1 -166.88(14) . . . . ?
C3B C6A C6 O1 -36.92(16) . . . . ?
C7 C6A C6 O1 68.57(17) . . . . ?
C11 C6A C6 C5 -61.07(18) . . . . ?
C3B C6A C6 C5 68.90(15) . . . . ?
C7 C6A C6 C5 174.38(13) . . . . ?
C9A O2 C7 C8 51.43(13) . . . . ?
C9A O2 C7 C6A -61.34(12) . . . . ?
C11 C6A C7 O2 170.71(12) . . . . ?
C3B C6A C7 O2 39.06(13) . . . . ?
C6 C6A C7 O2 -65.79(14) . . . . ?
C11 C6A C7 C8 65.27(16) . . . . ?
C3B C6A C7 C8 -66.38(14) . . . . ?
C6 C6A C7 C8 -171.23(12) . . . . ?
O2 C7 C8 C9 -31.99(16) . . . . ?
C6A C7 C8 C9 73.45(16) . . . . ?
C7 O2 C9A C1 -178.84(12) . . . . ?
C7 O2 C9A C9 -51.87(13) . . . . ?
C7 O2 C9A C3B 58.65(12) . . . . ?
N2 C1 C9A O2 -65.11(15) . . . . ?
N2 C1 C9A C9 179.62(13) . . . . ?
N2 C1 C9A C3B 48.95(16) . . . . ?
C10 C3B C9A O2 -160.74(11) . . . . ?
C6A C3B C9A O2 -32.41(12) . . . . ?
C3A C3B C9A O2 73.55(13) . . . . ?
C10 C3B C9A C1 80.38(15) . . . . ?
C6A C3B C9A C1 -151.28(12) . . . . ?
C3A C3B C9A C1 -45.32(16) . . . . ?
C10 C3B C9A C9 -55.87(15) . . . . ?
C6A C3B C9A C9 72.47(13) . . . . ?
C3A C3B C9A C9 178.42(12) . . . . ?
C7 C8 C9 C9A -0.84(17) . . . . ?
O2 C9A C9 C8 33.38(15) . . . . ?
C1 C9A C9 C8 153.66(14) . . . . ?
C3B C9A C9 C8 -72.38(15) . . . . ?
C6A C3B C10 F3 -45.65(19) . . . . ?
C3A C3B C10 F3 -165.56(13) . . . . ?
C9A C3B C10 F3 71.47(17) . . . . ?
C6A C3B C10 F4 76.92(18) . . . . ?
C3A C3B C10 F4 -43.00(18) . . . . ?
C9A C3B C10 F4 -165.97(13) . . . . ?
C6A C3B C10 F2 -164.86(13) . . . . ?
C3A C3B C10 F2 75.22(16) . . . . ?
C9A C3B C10 F2 -47.75(17) . . . . ?
C3B C6A C11 F6 78.2(2) . . . . ?
C7 C6A C11 F6 -40.4(2) . . . . ?
C6 C6A C11 F6 -166.49(16) . . . . ?
C3B C6A C11 F5 -45.8(2) . . . . ?
C7 C6A C11 F5 -164.35(14) . . . . ?
C6 C6A C11 F5 69.52(19) . . . . ?
C3B C6A C11 F7 -163.87(14) . . . . ?
C7 C6A C11 F7 77.59(17) . . . . ?
C6 C6A C11 F7 -48.53(19) . . . . ?
O3 S1 C12 C17 154.42(13) . . . . ?
O4 S1 C12 C17 22.89(15) . . . . ?
N2 S1 C12 C17 -90.93(13) . . . . ?
O3 S1 C12 C13 -26.65(16) . . . . ?
O4 S1 C12 C13 -158.19(14) . . . . ?
N2 S1 C12 C13 88.00(15) . . . . ?
C17 C12 C13 C14 0.1(3) . . . . ?
S1 C12 C13 C14 -178.77(16) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 F1 179.8(2) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
F1 C15 C16 C17 -179.47(17) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 0.2(2) . . . . ?
S1 C12 C17 C16 179.11(13) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.048


# start Validation Reply Form
_vrf_PLAT910_7a                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2023801'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C21 H17 F6 N O4 S'
_chemical_formula_sum            'C21 H17 F6 N O4 S'
_chemical_formula_weight         493.42

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.6619(4)
_cell_length_b                   19.6122(8)
_cell_length_c                   21.6230(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4097.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      30.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49338
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.094
_diffrn_reflns_theta_max         30.000
_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             5967
_reflns_number_gt                4538
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0607P)²+2.3469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         5967
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.54445(4) 0.10143(2) 0.58166(2) 0.01723(10) Uani 1 1 d . . . . .
F1 F 0.30732(11) 0.25356(6) 0.24357(5) 0.0344(3) Uani 1 1 d . . . . .
F2 F 0.52732(11) 0.25937(7) 0.23035(5) 0.0364(3) Uani 1 1 d . . . . .
F3 F 0.42177(15) 0.16434(7) 0.21681(5) 0.0428(3) Uani 1 1 d . . . . .
F4 F 0.21595(12) 0.12000(6) 0.28819(5) 0.0337(3) Uani 1 1 d . . . . .
F5 F 0.28764(16) 0.05506(6) 0.36072(7) 0.0551(4) Uani 1 1 d . . . . .
F6 F 0.15004(13) 0.13825(8) 0.38102(6) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.60402(13) 0.04548(6) 0.54834(6) 0.0222(3) Uani 1 1 d . . . . .
O2 O 0.62495(12) 0.13820(6) 0.62630(5) 0.0229(3) Uani 1 1 d . . . . .
O10 O 0.58065(11) 0.29567(6) 0.48905(5) 0.0183(2) Uani 1 1 d . . . . .
O11 O 0.58030(11) 0.19344(6) 0.40643(5) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.49421(14) 0.15727(7) 0.52956(6) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.43529(16) 0.22200(8) 0.55323(7) 0.0179(3) Uani 1 1 d . . . . .
H1A H 0.488677 0.237461 0.589706 0.022 Uiso 1 1 calc R U . . .
H1B H 0.338180 0.214654 0.566224 0.022 Uiso 1 1 calc R U . . .
C3 C 0.42457(18) 0.12907(8) 0.47445(7) 0.0185(3) Uani 1 1 d . . . . .
H3A H 0.325555 0.120710 0.483464 0.022 Uiso 1 1 calc R U . . .
H3B H 0.467869 0.085265 0.462482 0.022 Uiso 1 1 calc R U . . .
C3A C 0.43868(16) 0.18004(8) 0.42272(7) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.37896(17) 0.16452(8) 0.35835(8) 0.0198(3) Uani 1 1 d . . . . .
C5 C 0.44927(17) 0.20446(9) 0.31966(8) 0.0201(3) Uani 1 1 d . . . . .
C6A C 0.46428(16) 0.29842(8) 0.39457(8) 0.0183(3) Uani 1 1 d . . . . .
H6AA H 0.402459 0.325114 0.366469 0.022 Uiso 1 1 calc R U . . .
C6 C 0.55216(16) 0.24392(9) 0.35985(8) 0.0192(3) Uani 1 1 d . . . . .
H6A H 0.635285 0.261893 0.337639 0.023 Uiso 1 1 calc R U . . .
C7 C 0.54430(17) 0.34399(8) 0.44147(8) 0.0207(3) Uani 1 1 d . . . . .
H7A H 0.623643 0.370220 0.423690 0.025 Uiso 1 1 calc R U . . .
C8 C 0.43550(19) 0.38679(9) 0.47437(9) 0.0244(4) Uani 1 1 d . . . . .
H8A H 0.416783 0.433859 0.468234 0.029 Uiso 1 1 calc R U . . .
C9A C 0.44068(15) 0.27573(8) 0.50341(7) 0.0168(3) Uani 1 1 d . . . . .
C9B C 0.38354(15) 0.25172(8) 0.43978(7) 0.0160(3) Uani 1 1 d . . . . .
H9BA H 0.280754 0.256014 0.436023 0.019 Uiso 1 1 calc R U . . .
C9 C 0.37201(18) 0.34485(8) 0.51344(8) 0.0220(3) Uani 1 1 d . . . . .
H9A H 0.299593 0.355603 0.541517 0.026 Uiso 1 1 calc R U . . .
C10 C 0.2580(2) 0.11940(9) 0.34687(8) 0.0258(4) Uani 1 1 d . . . . .
C11 C 0.42619(19) 0.21951(10) 0.25277(8) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.39277(17) 0.07229(8) 0.61851(7) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.31585(18) 0.01880(8) 0.59302(8) 0.0221(3) Uani 1 1 d . . . . .
H13A H 0.345973 -0.003325 0.556324 0.027 Uiso 1 1 calc R U . . .
C14 C 0.19473(19) -0.00138(9) 0.62228(9) 0.0262(4) Uani 1 1 d . . . . .
H14A H 0.142225 -0.037866 0.605401 0.031 Uiso 1 1 calc R U . . .
C15 C 0.14842(19) 0.03088(9) 0.67610(9) 0.0260(4) Uani 1 1 d . . . . .
C16 C 0.22642(19) 0.08434(9) 0.70021(8) 0.0250(4) Uani 1 1 d . . . . .
H16A H 0.195900 0.106845 0.736650 0.030 Uiso 1 1 calc R U . . .
C17 C 0.34800(18) 0.10524(9) 0.67185(8) 0.0218(3) Uani 1 1 d . . . . .
H17A H 0.400303 0.141795 0.688730 0.026 Uiso 1 1 calc R U . . .
C18 C 0.0163(2) 0.00857(12) 0.70678(12) 0.0412(5) Uani 1 1 d . . . . .
H18A H 0.023635 0.015634 0.751529 0.062 Uiso 1 1 calc R U . . .
H18B H 0.000330 -0.039873 0.698289 0.062 Uiso 1 1 calc R U . . .
H18C H -0.061100 0.035421 0.690521 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 1.4333(12) . ?
S1 O2 1.4340(13) . ?
S1 N2 1.6445(14) . ?
S1 C12 1.7632(17) . ?
F1 C11 1.343(2) . ?
F2 C11 1.342(2) . ?
F3 C11 1.333(2) . ?
F4 C10 1.332(2) . ?
F5 C10 1.328(2) . ?
F6 C10 1.330(2) . ?
O10 C9A 1.4417(18) . ?
O10 C7 1.442(2) . ?
O11 C3A 1.4371(19) . ?
O11 C6 1.4381(19) . ?
N2 C3 1.476(2) . ?
N2 C1 1.482(2) . ?
C1 C9A 1.508(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C3A 1.506(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.537(2) . ?
C3A C9B 1.548(2) . ?
C4 C5 1.332(2) . ?
C4 C10 1.487(2) . ?
C5 C11 1.493(2) . ?
C5 C6 1.530(2) . ?
C6A C9B 1.550(2) . ?
C6A C7 1.557(2) . ?
C6A C6 1.558(2) . ?
C6A H6AA 1.0000 . ?
C6 H6A 1.0000 . ?
C7 C8 1.522(2) . ?
C7 H7A 1.0000 . ?
C8 C9 1.329(2) . ?
C8 H8A 0.9500 . ?
C9A C9 1.525(2) . ?
C9A C9B 1.555(2) . ?
C9B H9BA 1.0000 . ?
C9 H9A 0.9500 . ?
C12 C17 1.391(2) . ?
C12 C13 1.399(2) . ?
C13 C14 1.388(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.392(3) . ?
C15 C18 1.503(3) . ?
C16 C17 1.387(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 O2 120.36(8) . . ?
O1 S1 N2 106.50(7) . . ?
O2 S1 N2 106.64(7) . . ?
O1 S1 C12 108.23(8) . . ?
O2 S1 C12 108.03(8) . . ?
N2 S1 C12 106.27(7) . . ?
C9A O10 C7 95.94(11) . . ?
C3A O11 C6 96.75(11) . . ?
C3 N2 C1 115.13(13) . . ?
C3 N2 S1 115.98(10) . . ?
C1 N2 S1 116.56(10) . . ?
N2 C1 C9A 109.79(12) . . ?
N2 C1 H1A 109.7 . . ?
C9A C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C9A C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C3 C3A 108.03(13) . . ?
N2 C3 H3A 110.1 . . ?
C3A C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C3A C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
O11 C3A C3 112.93(13) . . ?
O11 C3A C4 99.88(12) . . ?
C3 C3A C4 120.46(13) . . ?
O11 C3A C9B 102.71(12) . . ?
C3 C3A C9B 113.24(13) . . ?
C4 C3A C9B 105.45(12) . . ?
C5 C4 C10 130.24(15) . . ?
C5 C4 C3A 105.11(14) . . ?
C10 C4 C3A 124.34(14) . . ?
C4 C5 C11 130.42(16) . . ?
C4 C5 C6 105.78(14) . . ?
C11 C5 C6 123.17(15) . . ?
C9B C6A C7 100.27(12) . . ?
C9B C6A C6 99.95(12) . . ?
C7 C6A C6 115.91(13) . . ?
C9B C6A H6AA 113.1 . . ?
C7 C6A H6AA 113.1 . . ?
C6 C6A H6AA 113.1 . . ?
O11 C6 C5 99.93(13) . . ?
O11 C6 C6A 103.76(12) . . ?
C5 C6 C6A 105.46(13) . . ?
O11 C6 H6A 115.3 . . ?
C5 C6 H6A 115.3 . . ?
C6A C6 H6A 115.3 . . ?
O10 C7 C8 101.37(13) . . ?
O10 C7 C6A 102.02(12) . . ?
C8 C7 C6A 106.14(13) . . ?
O10 C7 H7A 115.2 . . ?
C8 C7 H7A 115.2 . . ?
C6A C7 H7A 115.2 . . ?
C9 C8 C7 105.94(14) . . ?
C9 C8 H8A 127.0 . . ?
C7 C8 H8A 127.0 . . ?
O10 C9A C1 112.08(12) . . ?
O10 C9A C9 101.40(12) . . ?
C1 C9A C9 120.31(14) . . ?
O10 C9A C9B 102.97(12) . . ?
C1 C9A C9B 114.09(13) . . ?
C9 C9A C9B 103.92(13) . . ?
C3A C9B C6A 102.31(12) . . ?
C3A C9B C9A 111.32(12) . . ?
C6A C9B C9A 101.56(12) . . ?
C3A C9B H9BA 113.5 . . ?
C6A C9B H9BA 113.5 . . ?
C9A C9B H9BA 113.5 . . ?
C8 C9 C9A 105.01(15) . . ?
C8 C9 H9A 127.5 . . ?
C9A C9 H9A 127.5 . . ?
F5 C10 F6 107.93(17) . . ?
F5 C10 F4 106.78(15) . . ?
F6 C10 F4 106.69(15) . . ?
F5 C10 C4 110.99(16) . . ?
F6 C10 C4 111.00(15) . . ?
F4 C10 C4 113.17(15) . . ?
F3 C11 F2 106.59(15) . . ?
F3 C11 F1 106.84(15) . . ?
F2 C11 F1 106.23(15) . . ?
F3 C11 C5 114.17(15) . . ?
F2 C11 C5 110.88(15) . . ?
F1 C11 C5 111.68(15) . . ?
C17 C12 C13 120.66(15) . . ?
C17 C12 S1 118.85(13) . . ?
C13 C12 S1 120.44(12) . . ?
C14 C13 C12 118.83(15) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
C13 C14 C15 121.34(16) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C16 C15 C14 118.63(16) . . ?
C16 C15 C18 120.89(17) . . ?
C14 C15 C18 120.48(17) . . ?
C17 C16 C15 121.02(16) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C16 C17 C12 119.51(16) . . ?
C16 C17 H17A 120.2 . . ?
C12 C17 H17A 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 S1 N2 C3 42.64(13) . . . . ?
O2 S1 N2 C3 172.33(11) . . . . ?
C12 S1 N2 C3 -72.59(13) . . . . ?
O1 S1 N2 C1 -176.85(11) . . . . ?
O2 S1 N2 C1 -47.16(13) . . . . ?
C12 S1 N2 C1 67.92(13) . . . . ?
C3 N2 C1 C9A -58.67(17) . . . . ?
S1 N2 C1 C9A 160.49(11) . . . . ?
C1 N2 C3 C3A 61.66(17) . . . . ?
S1 N2 C3 C3A -157.26(11) . . . . ?
C6 O11 C3A C3 -177.79(13) . . . . ?
C6 O11 C3A C4 52.99(13) . . . . ?
C6 O11 C3A C9B -55.47(13) . . . . ?
N2 C3 C3A O11 60.95(16) . . . . ?
N2 C3 C3A C4 178.66(13) . . . . ?
N2 C3 C3A C9B -55.25(17) . . . . ?
O11 C3A C4 C5 -33.66(16) . . . . ?
C3 C3A C4 C5 -157.80(15) . . . . ?
C9B C3A C4 C5 72.59(16) . . . . ?
O11 C3A C4 C10 152.19(16) . . . . ?
C3 C3A C4 C10 28.1(2) . . . . ?
C9B C3A C4 C10 -101.56(18) . . . . ?
C10 C4 C5 C11 3.1(3) . . . . ?
C3A C4 C5 C11 -170.61(17) . . . . ?
C10 C4 C5 C6 174.04(17) . . . . ?
C3A C4 C5 C6 0.37(17) . . . . ?
C3A O11 C6 C5 -52.76(13) . . . . ?
C3A O11 C6 C6A 55.99(13) . . . . ?
C4 C5 C6 O11 33.00(16) . . . . ?
C11 C5 C6 O11 -155.20(15) . . . . ?
C4 C5 C6 C6A -74.40(16) . . . . ?
C11 C5 C6 C6A 97.41(18) . . . . ?
C9B C6A C6 O11 -33.88(14) . . . . ?
C7 C6A C6 O11 72.77(16) . . . . ?
C9B C6A C6 C5 70.71(14) . . . . ?
C7 C6A C6 C5 177.36(13) . . . . ?
C9A O10 C7 C8 50.55(14) . . . . ?
C9A O10 C7 C6A -58.89(13) . . . . ?
C9B C6A C7 O10 38.55(14) . . . . ?
C6 C6A C7 O10 -67.90(16) . . . . ?
C9B C6A C7 C8 -67.21(15) . . . . ?
C6 C6A C7 C8 -173.66(13) . . . . ?
O10 C7 C8 C9 -31.72(17) . . . . ?
C6A C7 C8 C9 74.51(17) . . . . ?
C7 O10 C9A C1 179.07(13) . . . . ?
C7 O10 C9A C9 -51.33(14) . . . . ?
C7 O10 C9A C9B 56.02(13) . . . . ?
N2 C1 C9A O10 -67.79(16) . . . . ?
N2 C1 C9A C9 173.25(13) . . . . ?
N2 C1 C9A C9B 48.74(17) . . . . ?
O11 C3A C9B C6A 34.16(14) . . . . ?
C3 C3A C9B C6A 156.27(13) . . . . ?
C4 C3A C9B C6A -70.01(14) . . . . ?
O11 C3A C9B C9A -73.61(14) . . . . ?
C3 C3A C9B C9A 48.49(17) . . . . ?
C4 C3A C9B C9A -177.79(12) . . . . ?
C7 C6A C9B C3A -119.10(13) . . . . ?
C6 C6A C9B C3A -0.24(14) . . . . ?
C7 C6A C9B C9A -3.99(14) . . . . ?
C6 C6A C9B C9A 114.87(12) . . . . ?
O10 C9A C9B C3A 76.66(14) . . . . ?
C1 C9A C9B C3A -45.04(17) . . . . ?
C9 C9A C9B C3A -177.91(12) . . . . ?
O10 C9A C9B C6A -31.60(14) . . . . ?
C1 C9A C9B C6A -153.30(13) . . . . ?
C9 C9A C9B C6A 73.83(14) . . . . ?
C7 C8 C9 C9A -1.06(18) . . . . ?
O10 C9A C9 C8 33.57(17) . . . . ?
C1 C9A C9 C8 157.76(15) . . . . ?
C9B C9A C9 C8 -73.04(16) . . . . ?
C5 C4 C10 F5 120.2(2) . . . . ?
C3A C4 C10 F5 -67.2(2) . . . . ?
C5 C4 C10 F6 -119.7(2) . . . . ?
C3A C4 C10 F6 52.9(2) . . . . ?
C5 C4 C10 F4 0.2(3) . . . . ?
C3A C4 C10 F4 172.78(15) . . . . ?
C4 C5 C11 F3 -55.6(3) . . . . ?
C6 C5 C11 F3 134.83(17) . . . . ?
C4 C5 C11 F2 -175.96(17) . . . . ?
C6 C5 C11 F2 14.4(2) . . . . ?
C4 C5 C11 F1 65.8(3) . . . . ?
C6 C5 C11 F1 -103.83(18) . . . . ?
O1 S1 C12 C17 153.79(13) . . . . ?
O2 S1 C12 C17 21.97(16) . . . . ?
N2 S1 C12 C17 -92.16(14) . . . . ?
O1 S1 C12 C13 -28.85(16) . . . . ?
O2 S1 C12 C13 -160.68(13) . . . . ?
N2 S1 C12 C13 85.20(15) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
S1 C12 C13 C14 -178.04(13) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 C18 179.51(19) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C18 C15 C16 C17 -179.70(19) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
S1 C12 C17 C16 177.90(13) . . . . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.066


# start Validation Reply Form
_vrf_PLAT910_6b                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_9a
_database_code_depnum_ccdc_archive 'CCDC 2023806'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C20 H14 Br F6 N O4 S'
_chemical_formula_sum            'C20 H14 Br F6 N O4 S'
_chemical_formula_weight         558.29

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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 '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                   12.1236(3)
_cell_length_b                   15.5201(4)
_cell_length_c                   10.6655(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.754(1)
_cell_angle_gamma                90
_cell_volume                     1964.73(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      35.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    2.286
_shelx_estimated_absorpt_T_min   0.462
_shelx_estimated_absorpt_T_max   0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_T_max  0.510
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70216
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.118
_diffrn_reflns_theta_max         35.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8629
_reflns_number_gt                7430
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0303P)²+0.6488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         8629
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_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 0.24745(2) 0.68363(2) 0.36893(2) 0.01316(4) Uani 1 1 d . . . . .
F1 F 0.53774(6) 0.32337(5) 0.80880(7) 0.02746(15) Uani 1 1 d . . . . .
F2 F 0.36867(6) 0.27415(4) 0.77293(7) 0.02494(14) Uani 1 1 d . . . . .
F3 F 0.41537(6) 0.37752(4) 0.90641(6) 0.02036(12) Uani 1 1 d . . . . .
F4 F 0.12112(5) 0.51030(5) 0.71225(6) 0.02390(13) Uani 1 1 d . . . . .
F5 F 0.25648(5) 0.51114(4) 0.87658(6) 0.01950(12) Uani 1 1 d . . . . .
F6 F 0.19389(6) 0.39103(4) 0.79148(6) 0.02107(12) Uani 1 1 d . . . . .
O1 O 0.34558(6) 0.73660(5) 0.40509(8) 0.01916(13) Uani 1 1 d . . . . .
O2 O 0.22779(6) 0.63648(5) 0.25084(7) 0.01787(13) Uani 1 1 d . . . . .
O10 O 0.33033(6) 0.43935(4) 0.46869(6) 0.01369(11) Uani 1 1 d . . . . .
O11 O 0.45250(5) 0.54660(4) 0.61231(6) 0.01312(11) Uani 1 1 d . . . . .
N2 N 0.24997(7) 0.61420(5) 0.48303(8) 0.01445(13) Uani 1 1 d . . . . .
C1 C 0.17647(8) 0.53825(6) 0.46147(9) 0.01440(15) Uani 1 1 d . . . . .
H1A H 0.153667 0.526738 0.368493 0.017 Uiso 1 1 calc R U . . .
H1B H 0.107590 0.548934 0.495500 0.017 Uiso 1 1 calc R U . . .
C3 C 0.29476(8) 0.63984(6) 0.61620(9) 0.01424(15) Uani 1 1 d . . . . .
H3A H 0.232147 0.651318 0.660705 0.017 Uiso 1 1 calc R U . . .
H3B H 0.340277 0.692990 0.618478 0.017 Uiso 1 1 calc R U . . .
C3A C 0.36708(7) 0.56699(6) 0.68137(8) 0.01179(14) Uani 1 1 d . . . . .
C4 C 0.43714(8) 0.57780(6) 0.81668(9) 0.01495(15) Uani 1 1 d . . . . .
H4A H 0.423604 0.616045 0.881448 0.018 Uiso 1 1 calc R U . . .
C5 C 0.52147(8) 0.52172(6) 0.82381(9) 0.01606(16) Uani 1 1 d . . . . .
H5A H 0.580461 0.510990 0.895603 0.019 Uiso 1 1 calc R U . . .
C6A C 0.40201(7) 0.41215(6) 0.68374(8) 0.01227(14) Uani 1 1 d . . . . .
C6 C 0.50372(7) 0.47838(6) 0.69304(9) 0.01432(15) Uani 1 1 d . . . . .
H6A H 0.573380 0.453904 0.670277 0.017 Uiso 1 1 calc R U . . .
C7 C 0.37075(8) 0.36710(6) 0.54765(9) 0.01494(15) Uani 1 1 d . . . . .
H7A H 0.433847 0.334759 0.521705 0.018 Uiso 1 1 calc R U . . .
C8 C 0.26216(9) 0.31591(6) 0.53872(9) 0.01771(17) Uani 1 1 d . . . . .
H8A H 0.254707 0.255062 0.541931 0.021 Uiso 1 1 calc R U . . .
C9A C 0.23893(7) 0.46109(6) 0.52817(8) 0.01218(14) Uani 1 1 d . . . . .
C9B C 0.30207(7) 0.47753(6) 0.67279(8) 0.01130(13) Uani 1 1 d . . . . .
C9 C 0.17962(8) 0.37426(6) 0.52544(9) 0.01641(16) Uani 1 1 d . . . . .
H9A H 0.101152 0.363932 0.516298 0.020 Uiso 1 1 calc R U . . .
C10 C 0.42905(8) 0.34705(6) 0.79283(9) 0.01636(16) Uani 1 1 d . . . . .
C11 C 0.22023(8) 0.47172(6) 0.76434(9) 0.01477(15) Uani 1 1 d . . . . .
C12 C 0.12903(8) 0.74994(6) 0.36702(8) 0.01296(14) Uani 1 1 d . . . . .
C13 C 0.13673(8) 0.81719(6) 0.45465(9) 0.01631(16) Uani 1 1 d . . . . .
H13A H 0.205536 0.827967 0.513296 0.020 Uiso 1 1 calc R U . . .
C14 C 0.04306(9) 0.86838(6) 0.45569(9) 0.01759(16) Uani 1 1 d . . . . .
H14A H 0.046856 0.914378 0.515186 0.021 Uiso 1 1 calc R U . . .
C15 C -0.05629(8) 0.85142(6) 0.36852(9) 0.01568(15) Uani 1 1 d . . . . .
C16 C -0.06513(8) 0.78396(6) 0.28140(9) 0.01698(16) Uani 1 1 d . . . . .
H16A H -0.134150 0.773122 0.223158 0.020 Uiso 1 1 calc R U . . .
C17 C 0.02865(8) 0.73263(6) 0.28089(9) 0.01578(16) Uani 1 1 d . . . . .
H17A H 0.024383 0.686072 0.222260 0.019 Uiso 1 1 calc R U . . .
Br1 Br -0.18348(2) 0.92197(2) 0.36603(2) 0.02301(3) 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
S1 O1 1.4328(8) . ?
S1 O2 1.4340(8) . ?
S1 N2 1.6210(8) . ?
S1 C12 1.7633(9) . ?
F1 C10 1.3450(12) . ?
F2 C10 1.3407(12) . ?
F3 C10 1.3418(11) . ?
F4 C11 1.3561(11) . ?
F5 C11 1.3364(11) . ?
F6 C11 1.3386(12) . ?
O10 C9A 1.4249(11) . ?
O10 C7 1.4278(11) . ?
O11 C3A 1.4232(11) . ?
O11 C6 1.4249(11) . ?
N2 C1 1.4673(12) . ?
N2 C3 1.4684(12) . ?
C1 C9A 1.5146(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C3A 1.5106(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.5274(12) . ?
C3A C9B 1.5900(12) . ?
C4 C5 1.3331(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.5237(14) . ?
C5 H5A 0.9500 . ?
C6A C10 1.5254(13) . ?
C6A C9B 1.5663(12) . ?
C6A C7 1.5859(13) . ?
C6A C6 1.5928(13) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5239(14) . ?
C7 H7A 1.0000 . ?
C8 C9 1.3355(15) . ?
C8 H8A 0.9500 . ?
C9A C9 1.5249(13) . ?
C9A C9B 1.5967(12) . ?
C9B C11 1.5300(13) . ?
C9 H9A 0.9500 . ?
C12 C13 1.3914(13) . ?
C12 C17 1.3934(13) . ?
C13 C14 1.3879(14) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3886(14) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3894(14) . ?
C15 Br1 1.8871(9) . ?
C16 C17 1.3893(13) . ?
C16 H16A 0.9500 . ?
C17 H17A 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 O2 120.63(5) . . ?
O1 S1 N2 106.96(4) . . ?
O2 S1 N2 107.13(4) . . ?
O1 S1 C12 107.32(5) . . ?
O2 S1 C12 107.36(4) . . ?
N2 S1 C12 106.70(4) . . ?
C9A O10 C7 97.35(7) . . ?
C3A O11 C6 97.24(7) . . ?
C1 N2 C3 117.54(8) . . ?
C1 N2 S1 119.90(6) . . ?
C3 N2 S1 119.52(6) . . ?
N2 C1 C9A 109.39(7) . . ?
N2 C1 H1A 109.8 . . ?
C9A C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C9A C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C3 C3A 107.93(7) . . ?
N2 C3 H3A 110.1 . . ?
C3A C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C3A C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
O11 C3A C3 110.10(7) . . ?
O11 C3A C4 100.97(7) . . ?
C3 C3A C4 120.76(8) . . ?
O11 C3A C9B 100.40(7) . . ?
C3 C3A C9B 113.12(7) . . ?
C4 C3A C9B 108.91(7) . . ?
C5 C4 C3A 104.74(8) . . ?
C5 C4 H4A 127.6 . . ?
C3A C4 H4A 127.6 . . ?
C4 C5 C6 105.81(8) . . ?
C4 C5 H5A 127.1 . . ?
C6 C5 H5A 127.1 . . ?
C10 C6A C9B 121.92(7) . . ?
C10 C6A C7 112.34(7) . . ?
C9B C6A C7 100.39(7) . . ?
C10 C6A C6 109.67(7) . . ?
C9B C6A C6 99.44(7) . . ?
C7 C6A C6 112.28(7) . . ?
O11 C6 C5 100.83(7) . . ?
O11 C6 C6A 101.85(7) . . ?
C5 C6 C6A 107.76(7) . . ?
O11 C6 H6A 114.9 . . ?
C5 C6 H6A 114.9 . . ?
C6A C6 H6A 114.9 . . ?
O10 C7 C8 100.62(7) . . ?
O10 C7 C6A 100.54(7) . . ?
C8 C7 C6A 109.23(7) . . ?
O10 C7 H7A 114.9 . . ?
C8 C7 H7A 114.9 . . ?
C6A C7 H7A 114.9 . . ?
C9 C8 C7 105.80(8) . . ?
C9 C8 H8A 127.1 . . ?
C7 C8 H8A 127.1 . . ?
O10 C9A C1 109.75(7) . . ?
O10 C9A C9 100.88(7) . . ?
C1 C9A C9 120.07(8) . . ?
O10 C9A C9B 101.81(7) . . ?
C1 C9A C9B 115.01(7) . . ?
C9 C9A C9B 106.92(7) . . ?
C11 C9B C6A 120.44(7) . . ?
C11 C9B C3A 113.14(7) . . ?
C6A C9B C3A 101.22(7) . . ?
C11 C9B C9A 111.19(7) . . ?
C6A C9B C9A 100.36(7) . . ?
C3A C9B C9A 109.24(7) . . ?
C8 C9 C9A 104.89(8) . . ?
C8 C9 H9A 127.6 . . ?
C9A C9 H9A 127.6 . . ?
F2 C10 F3 106.05(8) . . ?
F2 C10 F1 106.18(8) . . ?
F3 C10 F1 106.26(8) . . ?
F2 C10 C6A 114.37(8) . . ?
F3 C10 C6A 114.09(8) . . ?
F1 C10 C6A 109.29(8) . . ?
F5 C11 F6 106.50(7) . . ?
F5 C11 F4 105.49(8) . . ?
F6 C11 F4 105.73(8) . . ?
F5 C11 C9B 114.02(8) . . ?
F6 C11 C9B 114.04(8) . . ?
F4 C11 C9B 110.38(7) . . ?
C13 C12 C17 121.17(9) . . ?
C13 C12 S1 119.14(7) . . ?
C17 C12 S1 119.65(7) . . ?
C14 C13 C12 119.45(9) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 119.05(9) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C14 C15 C16 121.93(9) . . ?
C14 C15 Br1 119.62(7) . . ?
C16 C15 Br1 118.45(7) . . ?
C17 C16 C15 118.88(9) . . ?
C17 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C16 C17 C12 119.49(9) . . ?
C16 C17 H17A 120.3 . . ?
C12 C17 H17A 120.3 . . ?

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
O1 S1 N2 C1 -165.32(7) . . . . ?
O2 S1 N2 C1 -34.67(9) . . . . ?
C12 S1 N2 C1 80.07(8) . . . . ?
O1 S1 N2 C3 34.90(8) . . . . ?
O2 S1 N2 C3 165.54(7) . . . . ?
C12 S1 N2 C3 -79.71(8) . . . . ?
C3 N2 C1 C9A -57.89(11) . . . . ?
S1 N2 C1 C9A 141.93(7) . . . . ?
C1 N2 C3 C3A 62.12(10) . . . . ?
S1 N2 C3 C3A -137.63(7) . . . . ?
C6 O11 C3A C3 -179.55(7) . . . . ?
C6 O11 C3A C4 51.72(8) . . . . ?
C6 O11 C3A C9B -60.06(7) . . . . ?
N2 C3 C3A O11 55.82(9) . . . . ?
N2 C3 C3A C4 172.79(8) . . . . ?
N2 C3 C3A C9B -55.59(10) . . . . ?
O11 C3A C4 C5 -33.19(9) . . . . ?
C3 C3A C4 C5 -154.70(9) . . . . ?
C9B C3A C4 C5 71.92(9) . . . . ?
C3A C4 C5 C6 0.94(10) . . . . ?
C3A O11 C6 C5 -50.97(8) . . . . ?
C3A O11 C6 C6A 59.98(7) . . . . ?
C4 C5 C6 O11 31.51(9) . . . . ?
C4 C5 C6 C6A -74.79(9) . . . . ?
C10 C6A C6 O11 -163.48(7) . . . . ?
C9B C6A C6 O11 -34.53(8) . . . . ?
C7 C6A C6 O11 70.87(9) . . . . ?
C10 C6A C6 C5 -57.89(9) . . . . ?
C9B C6A C6 C5 71.06(8) . . . . ?
C7 C6A C6 C5 176.47(7) . . . . ?
C9A O10 C7 C8 51.07(8) . . . . ?
C9A O10 C7 C6A -61.00(7) . . . . ?
C10 C6A C7 O10 169.90(7) . . . . ?
C9B C6A C7 O10 38.86(8) . . . . ?
C6 C6A C7 O10 -65.93(9) . . . . ?
C10 C6A C7 C8 64.63(10) . . . . ?
C9B C6A C7 C8 -66.41(9) . . . . ?
C6 C6A C7 C8 -171.20(7) . . . . ?
O10 C7 C8 C9 -31.67(9) . . . . ?
C6A C7 C8 C9 73.54(9) . . . . ?
C7 O10 C9A C1 -179.41(7) . . . . ?
C7 O10 C9A C9 -51.74(8) . . . . ?
C7 O10 C9A C9B 58.32(7) . . . . ?
N2 C1 C9A O10 -66.45(9) . . . . ?
N2 C1 C9A C9 177.48(8) . . . . ?
N2 C1 C9A C9B 47.59(10) . . . . ?
C10 C6A C9B C11 -6.46(12) . . . . ?
C7 C6A C9B C11 118.27(8) . . . . ?
C6 C6A C9B C11 -126.82(8) . . . . ?
C10 C6A C9B C3A 119.08(9) . . . . ?
C7 C6A C9B C3A -116.19(7) . . . . ?
C6 C6A C9B C3A -1.28(7) . . . . ?
C10 C6A C9B C9A -128.72(8) . . . . ?
C7 C6A C9B C9A -3.99(8) . . . . ?
C6 C6A C9B C9A 110.92(7) . . . . ?
O11 C3A C9B C11 166.95(7) . . . . ?
C3 C3A C9B C11 -75.78(9) . . . . ?
C4 C3A C9B C11 61.45(9) . . . . ?
O11 C3A C9B C6A 36.67(7) . . . . ?
C3 C3A C9B C6A 153.94(7) . . . . ?
C4 C3A C9B C6A -68.83(8) . . . . ?
O11 C3A C9B C9A -68.60(8) . . . . ?
C3 C3A C9B C9A 48.67(9) . . . . ?
C4 C3A C9B C9A -174.11(7) . . . . ?
O10 C9A C9B C11 -160.53(7) . . . . ?
C1 C9A C9B C11 80.89(9) . . . . ?
C9 C9A C9B C11 -55.15(9) . . . . ?
O10 C9A C9B C6A -31.97(8) . . . . ?
C1 C9A C9B C6A -150.55(7) . . . . ?
C9 C9A C9B C6A 73.40(8) . . . . ?
O10 C9A C9B C3A 73.89(8) . . . . ?
C1 C9A C9B C3A -44.69(10) . . . . ?
C9 C9A C9B C3A 179.26(7) . . . . ?
C7 C8 C9 C9A -0.73(10) . . . . ?
O10 C9A C9 C8 33.04(9) . . . . ?
C1 C9A C9 C8 153.62(9) . . . . ?
C9B C9A C9 C8 -73.00(9) . . . . ?
C9B C6A C10 F2 84.62(11) . . . . ?
C7 C6A C10 F2 -34.44(11) . . . . ?
C6 C6A C10 F2 -160.05(8) . . . . ?
C9B C6A C10 F3 -37.72(12) . . . . ?
C7 C6A C10 F3 -156.79(8) . . . . ?
C6 C6A C10 F3 77.60(10) . . . . ?
C9B C6A C10 F1 -156.51(8) . . . . ?
C7 C6A C10 F1 84.42(10) . . . . ?
C6 C6A C10 F1 -41.19(10) . . . . ?
C6A C9B C11 F5 83.83(10) . . . . ?
C3A C9B C11 F5 -35.95(10) . . . . ?
C9A C9B C11 F5 -159.33(7) . . . . ?
C6A C9B C11 F6 -38.80(11) . . . . ?
C3A C9B C11 F6 -158.58(7) . . . . ?
C9A C9B C11 F6 78.04(9) . . . . ?
C6A C9B C11 F4 -157.65(8) . . . . ?
C3A C9B C11 F4 82.57(9) . . . . ?
C9A C9B C11 F4 -40.81(10) . . . . ?
O1 S1 C12 C13 -33.59(9) . . . . ?
O2 S1 C12 C13 -164.64(8) . . . . ?
N2 S1 C12 C13 80.77(8) . . . . ?
O1 S1 C12 C17 148.39(8) . . . . ?
O2 S1 C12 C17 17.34(9) . . . . ?
N2 S1 C12 C17 -97.24(8) . . . . ?
C17 C12 C13 C14 -0.51(15) . . . . ?
S1 C12 C13 C14 -178.50(8) . . . . ?
C12 C13 C14 C15 -0.29(15) . . . . ?
C13 C14 C15 C16 0.88(15) . . . . ?
C13 C14 C15 Br1 -178.59(8) . . . . ?
C14 C15 C16 C17 -0.65(15) . . . . ?
Br1 C15 C16 C17 178.83(8) . . . . ?
C15 C16 C17 C12 -0.16(15) . . . . ?
C13 C12 C17 C16 0.74(15) . . . . ?
S1 C12 C17 C16 178.72(8) . . . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.063


# start Validation Reply Form
_vrf_PLAT910_9a                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         15 Note  
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 2023804'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C20 H14 Cl F6 N O4 S'
_chemical_formula_sum            'C20 H14 Cl F6 N O4 S'
_chemical_formula_weight         513.83

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.1445(5)
_cell_length_b                   15.3437(6)
_cell_length_c                   10.8727(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.776(1)
_cell_angle_gamma                90
_cell_volume                     1983.39(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6972
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      29.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.385
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27385
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5767
_reflns_number_gt                4235
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0441P)²+0.7050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         5767
_refine_ls_number_parameters     318
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.023
_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
Cl1 Cl 0.67577(5) 0.92588(4) 0.63178(6) 0.07683(19) Uani 1 1 d . . . . .
S1 S 0.26052(4) 0.68430(3) 0.62166(4) 0.04010(11) Uani 1 1 d . . . . .
F1A F 0.37621(11) 0.50666(12) 0.28030(14) 0.0734(5) Uani 0.938(3) 1 d . . P A 1
F2A F 0.30182(14) 0.38687(9) 0.20595(14) 0.0636(4) Uani 0.938(3) 1 d . . P A 1
F3A F 0.23980(12) 0.50677(10) 0.12253(11) 0.0605(4) Uani 0.938(3) 1 d . . P A 1
F4A F 0.07348(14) 0.37360(9) 0.09789(10) 0.0626(4) Uani 0.938(3) 1 d . . P A 1
F5A F 0.12610(16) 0.27140(9) 0.22792(14) 0.0760(5) Uani 0.938(3) 1 d . . P A 1
F6A F -0.04192(14) 0.32120(12) 0.20107(17) 0.0883(7) Uani 0.938(3) 1 d . . P A
1
F1B F 0.3548(12) 0.4095(9) 0.2532(18) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
F2B F 0.2124(14) 0.4579(12) 0.1179(11) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
F3B F 0.3229(15) 0.5477(7) 0.2309(17) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
F4B F 0.1611(10) 0.3046(13) 0.2002(17) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
F5B F 0.0104(14) 0.2815(10) 0.2642(17) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
F6B F 0.0063(14) 0.3624(12) 0.1020(11) 0.053(3) Uiso 0.062(3) 1 d D . P A 2
O1 O 0.05052(9) 0.54831(7) 0.38705(10) 0.0381(2) Uani 1 1 d . . . . .
O2 O 0.17221(10) 0.43934(7) 0.52668(10) 0.0392(3) Uani 1 1 d . . . . .
O3 O 0.16242(11) 0.73762(9) 0.58724(14) 0.0572(3) Uani 1 1 d . . . . .
O4 O 0.28069(12) 0.63657(9) 0.73705(12) 0.0539(3) Uani 1 1 d . . . . .
N2 N 0.25769(12) 0.61484(8) 0.50932(13) 0.0402(3) Uani 1 1 d . . . . .
C1 C 0.32804(14) 0.53630(11) 0.52932(16) 0.0412(4) Uani 1 1 d . . . . .
H1A H 0.351505 0.525090 0.618636 0.049 Uiso 1 1 calc R U . . .
H1B H 0.394912 0.545049 0.494961 0.049 Uiso 1 1 calc R U . . .
C3B C 0.19744(12) 0.47583(9) 0.32458(13) 0.0314(3) Uani 1 1 d . . . . .
C3A C 0.13481(12) 0.56723(10) 0.31724(13) 0.0331(3) Uani 1 1 d . . . . .
C3 C 0.20928(14) 0.64006(10) 0.37896(15) 0.0404(4) Uani 1 1 d . . . . .
H3A H 0.268922 0.650740 0.333578 0.048 Uiso 1 1 calc R U . . .
H3B H 0.165717 0.693140 0.377973 0.048 Uiso 1 1 calc R U . . .
C4 C 0.06306(15) 0.57852(11) 0.18584(15) 0.0429(4) Uani 1 1 d . . . . .
H4 H 0.076138 0.615883 0.123005 0.052 Uiso 1 1 calc R U . . .
C5 C -0.02155(15) 0.52387(12) 0.18050(17) 0.0472(4) Uani 1 1 d . . . . .
H5 H -0.080373 0.514194 0.112383 0.057 Uiso 1 1 calc R U . . .
C6A C 0.09606(13) 0.41138(10) 0.31683(14) 0.0351(3) Uani 1 1 d . . . . .
C6 C -0.00336(14) 0.47981(11) 0.30858(16) 0.0412(4) Uani 1 1 d . . . . .
H6 H -0.071681 0.456835 0.331642 0.049 Uiso 1 1 calc R U . . .
C7 C 0.12852(16) 0.36655(11) 0.45060(15) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.066746 0.335806 0.477491 0.051 Uiso 1 1 calc R U . . .
C8 C 0.23483(18) 0.31325(11) 0.45775(17) 0.0509(4) Uani 1 1 d . . . . .
H8 H 0.240213 0.252850 0.455082 0.061 Uiso 1 1 calc R U . . .
C9A C 0.26251(13) 0.45910(10) 0.46594(14) 0.0343(3) Uani 1 1 d . . . . .
C9 C 0.31822(16) 0.36983(11) 0.46854(16) 0.0461(4) Uani 1 1 d . . . . .
H9 H 0.394377 0.357850 0.476080 0.055 Uiso 1 1 calc R U . . .
C10 C 0.27633(15) 0.46859(12) 0.23243(16) 0.0431(4) Uani 1 1 d D . . . .
C11 C 0.06557(17) 0.34415(12) 0.21188(17) 0.0497(4) Uani 1 1 d D . . . .
C12 C 0.37836(14) 0.75252(10) 0.62444(14) 0.0358(3) Uani 1 1 d . . . . .
C13 C 0.37281(16) 0.81721(11) 0.53418(16) 0.0471(4) Uani 1 1 d . . . . .
H13 H 0.307617 0.824769 0.473265 0.056 Uiso 1 1 calc R U . . .
C14 C 0.46471(18) 0.87017(12) 0.53558(18) 0.0520(4) Uani 1 1 d . . . . .
H14 H 0.462274 0.913457 0.475213 0.062 Uiso 1 1 calc R U . . .
C15 C 0.56066(16) 0.85838(11) 0.62756(17) 0.0457(4) Uani 1 1 d . . . . .
C16 C 0.56681(16) 0.79409(13) 0.71697(17) 0.0500(4) Uani 1 1 d . . . . .
H16 H 0.632112 0.786629 0.777756 0.060 Uiso 1 1 calc R U . . .
C17 C 0.47496(15) 0.74080(12) 0.71539(16) 0.0439(4) Uani 1 1 d . . . . .
H17 H 0.478017 0.697136 0.775314 0.053 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
Cl1 C15 1.7329(18) . ?
S1 O4 1.4300(13) . ?
S1 O3 1.4307(14) . ?
S1 N2 1.6161(14) . ?
S1 C12 1.7682(16) . ?
F1A C10 1.351(2) . ?
F2A C10 1.337(2) . ?
F3A C10 1.323(2) . ?
F4A C11 1.341(2) . ?
F5A C11 1.328(2) . ?
F6A C11 1.334(2) . ?
F1B C10 1.301(9) . ?
F2B C10 1.336(9) . ?
F3B C10 1.340(8) . ?
F4B C11 1.338(9) . ?
F5B C11 1.361(9) . ?
F6B C11 1.294(9) . ?
O1 C3A 1.4231(19) . ?
O1 C6 1.4259(19) . ?
O2 C9A 1.4234(19) . ?
O2 C7 1.4263(19) . ?
N2 C1 1.468(2) . ?
N2 C3 1.471(2) . ?
C1 C9A 1.512(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3B C10 1.525(2) . ?
C3B C6A 1.568(2) . ?
C3B C3A 1.590(2) . ?
C3B C9A 1.599(2) . ?
C3A C3 1.506(2) . ?
C3A C4 1.524(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.318(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.523(2) . ?
C5 H5 0.9300 . ?
C6A C11 1.527(2) . ?
C6A C7 1.584(2) . ?
C6A C6 1.589(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.517(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.321(3) . ?
C8 H8 0.9300 . ?
C9A C9 1.525(2) . ?
C9 H9 0.9300 . ?
C12 C17 1.383(2) . ?
C12 C13 1.388(2) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 H17 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
O4 S1 O3 120.44(9) . . ?
O4 S1 N2 107.38(8) . . ?
O3 S1 N2 106.94(8) . . ?
O4 S1 C12 107.16(8) . . ?
O3 S1 C12 107.09(8) . . ?
N2 S1 C12 107.19(8) . . ?
C3A O1 C6 97.09(11) . . ?
C9A O2 C7 97.37(11) . . ?
C1 N2 C3 117.70(13) . . ?
C1 N2 S1 120.51(10) . . ?
C3 N2 S1 119.82(11) . . ?
N2 C1 C9A 109.84(12) . . ?
N2 C1 H1A 109.7 . . ?
C9A C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C9A C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C10 C3B C6A 120.69(13) . . ?
C10 C3B C3A 112.93(12) . . ?
C6A C3B C3A 101.02(11) . . ?
C10 C3B C9A 111.49(12) . . ?
C6A C3B C9A 100.31(11) . . ?
C3A C3B C9A 109.11(11) . . ?
O1 C3A C3 110.21(13) . . ?
O1 C3A C4 100.80(12) . . ?
C3 C3A C4 120.64(13) . . ?
O1 C3A C3B 100.50(11) . . ?
C3 C3A C3B 113.23(12) . . ?
C4 C3A C3B 108.88(12) . . ?
N2 C3 C3A 108.64(12) . . ?
N2 C3 H3A 110.0 . . ?
C3A C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C3A C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C3A 105.09(15) . . ?
C5 C4 H4 127.5 . . ?
C3A C4 H4 127.5 . . ?
C4 C5 C6 106.01(14) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
C11 C6A C3B 122.30(13) . . ?
C11 C6A C7 111.70(13) . . ?
C3B C6A C7 100.31(12) . . ?
C11 C6A C6 109.80(13) . . ?
C3B C6A C6 99.54(12) . . ?
C7 C6A C6 112.50(13) . . ?
O1 C6 C5 100.55(13) . . ?
O1 C6 C6A 101.69(12) . . ?
C5 C6 C6A 108.16(13) . . ?
O1 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C6A C6 H6 114.9 . . ?
O2 C7 C8 100.40(14) . . ?
O2 C7 C6A 100.71(12) . . ?
C8 C7 C6A 109.33(14) . . ?
O2 C7 H7 114.9 . . ?
C8 C7 H7 114.9 . . ?
C6A C7 H7 114.9 . . ?
C9 C8 C7 106.23(15) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
O2 C9A C1 109.81(13) . . ?
O2 C9A C9 100.43(13) . . ?
C1 C9A C9 120.30(14) . . ?
O2 C9A C3B 101.76(11) . . ?
C1 C9A C3B 115.03(12) . . ?
C9 C9A C3B 107.00(12) . . ?
C8 C9 C9A 105.03(16) . . ?
C8 C9 H9 127.5 . . ?
C9A C9 H9 127.5 . . ?
F1B C10 F2B 110.0(9) . . ?
F3A C10 F2A 105.69(14) . . ?
F1B C10 F3B 109.6(9) . . ?
F2B C10 F3B 105.5(9) . . ?
F3A C10 F1A 105.40(15) . . ?
F2A C10 F1A 105.04(16) . . ?
F1B C10 C3B 118.2(9) . . ?
F3A C10 C3B 114.90(14) . . ?
F2B C10 C3B 107.3(8) . . ?
F2A C10 C3B 114.45(14) . . ?
F3B C10 C3B 105.4(8) . . ?
F1A C10 C3B 110.51(14) . . ?
F5A C11 F6A 107.17(17) . . ?
F6B C11 F4B 109.9(9) . . ?
F5A C11 F4A 105.21(16) . . ?
F6A C11 F4A 105.13(16) . . ?
F6B C11 F5B 108.1(9) . . ?
F4B C11 F5B 103.3(9) . . ?
F6B C11 C6A 123.2(9) . . ?
F5A C11 C6A 115.24(16) . . ?
F6A C11 C6A 109.15(15) . . ?
F4B C11 C6A 107.1(9) . . ?
F4A C11 C6A 114.26(15) . . ?
F5B C11 C6A 103.3(8) . . ?
C17 C12 C13 120.68(16) . . ?
C17 C12 S1 120.05(13) . . ?
C13 C12 S1 119.27(13) . . ?
C14 C13 C12 119.44(16) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.44(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 121.37(17) . . ?
C16 C15 Cl1 118.85(15) . . ?
C14 C15 Cl1 119.79(15) . . ?
C15 C16 C17 119.24(16) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 119.82(16) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?

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
O4 S1 N2 C1 -32.63(15) . . . . ?
O3 S1 N2 C1 -163.19(13) . . . . ?
C12 S1 N2 C1 82.24(14) . . . . ?
O4 S1 N2 C3 163.69(13) . . . . ?
O3 S1 N2 C3 33.12(15) . . . . ?
C12 S1 N2 C3 -81.45(14) . . . . ?
C3 N2 C1 C9A -56.44(19) . . . . ?
S1 N2 C1 C9A 139.54(12) . . . . ?
C6 O1 C3A C3 -179.82(12) . . . . ?
C6 O1 C3A C4 51.63(13) . . . . ?
C6 O1 C3A C3B -60.11(12) . . . . ?
C10 C3B C3A O1 166.68(12) . . . . ?
C6A C3B C3A O1 36.36(13) . . . . ?
C9A C3B C3A O1 -68.74(13) . . . . ?
C10 C3B C3A C3 -75.81(16) . . . . ?
C6A C3B C3A C3 153.88(13) . . . . ?
C9A C3B C3A C3 48.77(16) . . . . ?
C10 C3B C3A C4 61.33(16) . . . . ?
C6A C3B C3A C4 -68.99(14) . . . . ?
C9A C3B C3A C4 -174.09(12) . . . . ?
C1 N2 C3 C3A 60.48(19) . . . . ?
S1 N2 C3 C3A -135.39(12) . . . . ?
O1 C3A C3 N2 56.69(17) . . . . ?
C4 C3A C3 N2 173.44(14) . . . . ?
C3B C3A C3 N2 -54.99(17) . . . . ?
O1 C3A C4 C5 -33.16(17) . . . . ?
C3 C3A C4 C5 -154.61(16) . . . . ?
C3B C3A C4 C5 71.99(17) . . . . ?
C3A C4 C5 C6 0.79(18) . . . . ?
C10 C3B C6A C11 -5.2(2) . . . . ?
C3A C3B C6A C11 120.08(16) . . . . ?
C9A C3B C6A C11 -127.93(16) . . . . ?
C10 C3B C6A C7 118.84(15) . . . . ?
C3A C3B C6A C7 -115.90(12) . . . . ?
C9A C3B C6A C7 -3.91(14) . . . . ?
C10 C3B C6A C6 -126.01(15) . . . . ?
C3A C3B C6A C6 -0.76(13) . . . . ?
C9A C3B C6A C6 111.24(12) . . . . ?
C3A O1 C6 C5 -50.93(14) . . . . ?
C3A O1 C6 C6A 60.31(13) . . . . ?
C4 C5 C6 O1 31.68(17) . . . . ?
C4 C5 C6 C6A -74.46(17) . . . . ?
C11 C6A C6 O1 -164.62(13) . . . . ?
C3B C6A C6 O1 -35.10(14) . . . . ?
C7 C6A C6 O1 70.33(15) . . . . ?
C11 C6A C6 C5 -59.27(17) . . . . ?
C3B C6A C6 C5 70.25(14) . . . . ?
C7 C6A C6 C5 175.67(13) . . . . ?
C9A O2 C7 C8 51.08(13) . . . . ?
C9A O2 C7 C6A -61.08(13) . . . . ?
C11 C6A C7 O2 169.86(13) . . . . ?
C3B C6A C7 O2 38.80(14) . . . . ?
C6 C6A C7 O2 -66.13(15) . . . . ?
C11 C6A C7 C8 64.74(18) . . . . ?
C3B C6A C7 C8 -66.33(15) . . . . ?
C6 C6A C7 C8 -171.25(13) . . . . ?
O2 C7 C8 C9 -31.60(17) . . . . ?
C6A C7 C8 C9 73.74(17) . . . . ?
C7 O2 C9A C1 -179.41(12) . . . . ?
C7 O2 C9A C9 -51.70(13) . . . . ?
C7 O2 C9A C3B 58.30(13) . . . . ?
N2 C1 C9A O2 -66.58(17) . . . . ?
N2 C1 C9A C9 177.73(14) . . . . ?
N2 C1 C9A C3B 47.45(18) . . . . ?
C10 C3B C9A O2 -161.01(12) . . . . ?
C6A C3B C9A O2 -32.02(13) . . . . ?
C3A C3B C9A O2 73.57(13) . . . . ?
C10 C3B C9A C1 80.35(17) . . . . ?
C6A C3B C9A C1 -150.66(13) . . . . ?
C3A C3B C9A C1 -45.07(17) . . . . ?
C10 C3B C9A C9 -56.11(17) . . . . ?
C6A C3B C9A C9 72.87(14) . . . . ?
C3A C3B C9A C9 178.46(13) . . . . ?
C7 C8 C9 C9A -0.87(18) . . . . ?
O2 C9A C9 C8 33.17(16) . . . . ?
C1 C9A C9 C8 153.62(16) . . . . ?
C3B C9A C9 C8 -72.67(17) . . . . ?
C6A C3B C10 F1B -80.0(10) . . . . ?
C3A C3B C10 F1B 160.5(9) . . . . ?
C9A C3B C10 F1B 37.2(10) . . . . ?
C6A C3B C10 F3A 82.7(2) . . . . ?
C3A C3B C10 F3A -36.8(2) . . . . ?
C9A C3B C10 F3A -160.09(15) . . . . ?
C6A C3B C10 F2B 45.0(9) . . . . ?
C3A C3B C10 F2B -74.5(9) . . . . ?
C9A C3B C10 F2B 162.3(9) . . . . ?
C6A C3B C10 F2A -39.9(2) . . . . ?
C3A C3B C10 F2A -159.40(15) . . . . ?
C9A C3B C10 F2A 77.32(18) . . . . ?
C6A C3B C10 F3B 157.1(8) . . . . ?
C3A C3B C10 F3B 37.6(8) . . . . ?
C9A C3B C10 F3B -85.7(8) . . . . ?
C6A C3B C10 F1A -158.21(15) . . . . ?
C3A C3B C10 F1A 82.28(18) . . . . ?
C9A C3B C10 F1A -41.00(19) . . . . ?
C3B C6A C11 F6B -82.1(10) . . . . ?
C7 C6A C11 F6B 159.2(10) . . . . ?
C6 C6A C11 F6B 33.7(10) . . . . ?
C3B C6A C11 F5A 81.5(2) . . . . ?
C7 C6A C11 F5A -37.1(2) . . . . ?
C6 C6A C11 F5A -162.61(16) . . . . ?
C3B C6A C11 F6A -157.85(17) . . . . ?
C7 C6A C11 F6A 83.5(2) . . . . ?
C6 C6A C11 F6A -42.0(2) . . . . ?
C3B C6A C11 F4B 46.8(9) . . . . ?
C7 C6A C11 F4B -71.8(9) . . . . ?
C6 C6A C11 F4B 162.7(8) . . . . ?
C3B C6A C11 F4A -40.5(2) . . . . ?
C7 C6A C11 F4A -159.14(16) . . . . ?
C6 C6A C11 F4A 75.35(19) . . . . ?
C3B C6A C11 F5B 155.5(8) . . . . ?
C7 C6A C11 F5B 36.8(8) . . . . ?
C6 C6A C11 F5B -88.7(8) . . . . ?
O4 S1 C12 C17 11.68(16) . . . . ?
O3 S1 C12 C17 142.20(14) . . . . ?
N2 S1 C12 C17 -103.33(14) . . . . ?
O4 S1 C12 C13 -168.71(13) . . . . ?
O3 S1 C12 C13 -38.19(15) . . . . ?
N2 S1 C12 C13 76.28(15) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
S1 C12 C13 C14 -179.61(14) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C13 C14 C15 Cl1 -178.86(15) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
Cl1 C15 C16 C17 179.10(14) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
S1 C12 C17 C16 179.84(14) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.047


# start Validation Reply Form
_vrf_PLAT910_8a                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 17 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 2023803'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C20 H14 F7 N O4 S'
_chemical_formula_sum            'C20 H14 F7 N O4 S'
_chemical_formula_weight         497.38

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.1261(11)
_cell_length_b                   5.3231(5)
_cell_length_c                   15.7434(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.951(6)
_cell_angle_gamma                90
_cell_volume                     1000.92(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2037
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      20.88

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10943
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.412
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.870
_reflns_number_total             3877
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_max     0.659
_reflns_Friedel_fraction_full    0.720

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.1410P)²+1.4957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3877
_refine_ls_number_parameters     320
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.2739
_refine_ls_wR_factor_gt          0.2438
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

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 0.54577(19) 0.2072(5) 0.66509(15) 0.0477(6) Uani 1 1 d . . . . .
F1A F 0.4239(10) 0.890(2) 0.8897(7) 0.078(4) Uani 0.624(19) 1 d D U P . .
F2A F 0.3072(11) 0.907(3) 0.9698(9) 0.098(5) Uani 0.624(19) 1 d D U P . .
F3A F 0.4346(13) 0.622(3) 0.9885(10) 0.120(6) Uani 0.624(19) 1 d D U P . .
F1B F 0.353(2) 0.968(3) 0.9276(17) 0.109(7) Uiso 0.376(19) 1 d D . P . .
F3B F 0.4748(14) 0.676(5) 0.9381(16) 0.109(7) Uiso 0.376(19) 1 d D . P . .
F2B F 0.353(2) 0.673(5) 1.0156(12) 0.109(7) Uiso 0.376(19) 1 d D . P . .
F4A F 0.0658(11) 0.755(2) 0.9263(9) 0.128(6) Uani 0.763(19) 1 d D U P . .
F5A F 0.0264(9) 0.373(3) 0.9213(7) 0.111(5) Uani 0.763(19) 1 d D U P . .
F6A F 0.1576(10) 0.512(3) 1.0192(6) 0.112(5) Uani 0.763(19) 1 d D U P . .
F4B F 0.0084(17) 0.551(7) 0.917(2) 0.104(10) Uiso 0.237(19) 1 d D . P . .
F5B F 0.128(3) 0.327(5) 0.994(2) 0.104(10) Uiso 0.237(19) 1 d D . P . .
F6B F 0.149(3) 0.717(6) 0.993(2) 0.104(10) Uiso 0.237(19) 1 d D . P . .
F7 F 0.9023(6) 0.9589(18) 0.7075(6) 0.098(3) Uani 1 1 d . . . . .
O1 O 0.1983(5) 0.3264(13) 0.6107(4) 0.0459(15) Uani 1 1 d . . . . .
O2 O 0.2620(5) 0.2332(13) 0.7792(4) 0.0469(15) Uani 1 1 d . . . . .
O3 O 0.5224(6) 0.1277(14) 0.5757(5) 0.0583(19) Uani 1 1 d . . . . .
O4 O 0.5694(6) 0.0259(14) 0.7323(5) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.4360(6) 0.3604(16) 0.6818(5) 0.048(2) Uani 1 1 d . . . . .
C1 C 0.3810(7) 0.5325(19) 0.6150(6) 0.044(2) Uani 1 1 d . . . . .
H1A H 0.386033 0.466132 0.558406 0.053 Uiso 1 1 calc R U . . .
H1B H 0.418114 0.694526 0.621109 0.053 Uiso 1 1 calc R U . . .
C3B C 0.2452(7) 0.6293(17) 0.7186(6) 0.0398(19) Uani 1 1 d . . . . .
H3BA H 0.251819 0.809562 0.730972 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4368(7) 0.444(2) 0.7721(6) 0.044(2) Uani 1 1 d . . . . .
H3A H 0.474879 0.604841 0.781904 0.053 Uiso 1 1 calc R U . . .
H3B H 0.476333 0.323044 0.812151 0.053 Uiso 1 1 calc R U . . .
C3A C 0.3176(7) 0.4693(17) 0.7862(6) 0.0387(19) Uani 1 1 d . . . . .
C4 C 0.2927(8) 0.557(2) 0.8742(6) 0.050(2) Uani 1 1 d . . . . .
C5 C 0.1921(9) 0.474(2) 0.8778(7) 0.058(3) Uani 1 1 d . . . . .
C6A C 0.1253(7) 0.524(2) 0.7207(7) 0.049(2) Uani 1 1 d . . . . .
H6AA H 0.073449 0.651994 0.735046 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1568(9) 0.327(2) 0.7927(7) 0.056(3) Uani 1 1 d . . . . .
H6A H 0.099858 0.197592 0.794926 0.068 Uiso 1 1 calc R U . . .
C7 C 0.0925(8) 0.423(2) 0.6276(7) 0.056(3) Uani 1 1 d . . . . .
H7A H 0.030151 0.303242 0.618594 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0781(9) 0.649(2) 0.5705(7) 0.057(3) Uani 1 1 d . . . . .
H8A H 0.010670 0.714561 0.542148 0.068 Uiso 1 1 calc R U . . .
C9A C 0.2582(8) 0.5631(16) 0.6238(6) 0.039(2) Uani 1 1 d . . . . .
C9 C 0.1792(9) 0.738(2) 0.5679(6) 0.052(2) Uani 1 1 d . . . . .
H9A H 0.197576 0.878162 0.538049 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3650(9) 0.730(2) 0.9331(6) 0.074(4) Uani 1 1 d D . . . .
C11 C 0.1159(11) 0.527(3) 0.9384(8) 0.100(5) Uani 1 1 d D U . . .
C12 C 0.6580(7) 0.424(2) 0.6771(6) 0.048(2) Uani 1 1 d . . . . .
C13 C 0.6775(8) 0.560(2) 0.6061(7) 0.053(3) Uani 1 1 d . . . . .
H13A H 0.634657 0.531273 0.552089 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7622(9) 0.740(3) 0.6166(8) 0.065(3) Uani 1 1 d . . . . .
H14A H 0.777709 0.831441 0.569730 0.078 Uiso 1 1 calc R U . . .
C15 C 0.8205(8) 0.778(2) 0.6958(9) 0.062(3) Uani 1 1 d . . . . .
C16 C 0.8050(9) 0.643(3) 0.7648(9) 0.073(4) Uani 1 1 d . . . . .
H16A H 0.850689 0.672780 0.817602 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7229(10) 0.460(3) 0.7595(8) 0.071(3) Uani 1 1 d . . . . .
H17A H 0.711417 0.366630 0.807201 0.085 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 O4 1.424(8) . ?
S1 O3 1.451(7) . ?
S1 N2 1.621(8) . ?
S1 C12 1.769(11) . ?
F1A C10 1.368(13) . ?
F2A C10 1.360(12) . ?
F3A C10 1.245(12) . ?
F1B C10 1.275(16) . ?
F3B C10 1.351(15) . ?
F2B C10 1.365(15) . ?
F4A C11 1.356(14) . ?
F5A C11 1.348(13) . ?
F6A C11 1.288(13) . ?
F4B C11 1.296(17) . ?
F5B C11 1.368(17) . ?
F6B C11 1.346(17) . ?
F7 C15 1.369(13) . ?
O1 C7 1.449(12) . ?
O1 C9A 1.451(10) . ?
O2 C6 1.419(12) . ?
O2 C3A 1.421(11) . ?
N2 C1 1.466(12) . ?
N2 C3 1.488(12) . ?
C1 C9A 1.528(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3B C3A 1.518(13) . ?
C3B C6A 1.564(12) . ?
C3B C9A 1.568(12) . ?
C3B H3BA 0.9800 . ?
C3 C3A 1.506(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.541(13) . ?
C4 C5 1.308(14) . ?
C4 C10 1.481(16) . ?
C5 C11 1.465(16) . ?
C5 C6 1.547(16) . ?
C6A C6 1.544(15) . ?
C6A C7 1.546(15) . ?
C6A H6AA 0.9800 . ?
C6 H6A 0.9800 . ?
C7 C8 1.494(16) . ?
C7 H7A 0.9800 . ?
C8 C9 1.321(14) . ?
C8 H8A 0.9300 . ?
C9A C9 1.505(14) . ?
C9 H9A 0.9300 . ?
C12 C13 1.386(14) . ?
C12 C17 1.410(15) . ?
C13 C14 1.393(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.339(16) . ?
C14 H14A 0.9300 . ?
C15 C16 1.344(18) . ?
C16 C17 1.385(19) . ?
C16 H16A 0.9300 . ?
C17 H17A 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
O4 S1 O3 120.2(5) . . ?
O4 S1 N2 106.6(4) . . ?
O3 S1 N2 106.1(4) . . ?
O4 S1 C12 108.1(5) . . ?
O3 S1 C12 108.2(4) . . ?
N2 S1 C12 107.0(5) . . ?
C7 O1 C9A 95.9(7) . . ?
C6 O2 C3A 96.0(7) . . ?
C1 N2 C3 115.1(8) . . ?
C1 N2 S1 118.8(6) . . ?
C3 N2 S1 115.9(6) . . ?
N2 C1 C9A 109.3(7) . . ?
N2 C1 H1A 109.8 . . ?
C9A C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C9A C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C3A C3B C6A 102.2(7) . . ?
C3A C3B C9A 113.6(7) . . ?
C6A C3B C9A 100.8(7) . . ?
C3A C3B H3BA 113.1 . . ?
C6A C3B H3BA 113.1 . . ?
C9A C3B H3BA 113.1 . . ?
N2 C3 C3A 108.6(7) . . ?
N2 C3 H3A 110.0 . . ?
C3A C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C3A C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O2 C3A C3 111.4(7) . . ?
O2 C3A C3B 103.5(7) . . ?
C3 C3A C3B 113.5(7) . . ?
O2 C3A C4 100.0(7) . . ?
C3 C3A C4 120.1(8) . . ?
C3B C3A C4 106.3(7) . . ?
C5 C4 C10 129.7(9) . . ?
C5 C4 C3A 105.4(9) . . ?
C10 C4 C3A 124.4(9) . . ?
C4 C5 C11 131.4(11) . . ?
C4 C5 C6 104.7(8) . . ?
C11 C5 C6 123.3(10) . . ?
C6 C6A C7 116.8(9) . . ?
C6 C6A C3B 98.4(7) . . ?
C7 C6A C3B 101.1(7) . . ?
C6 C6A H6AA 113.0 . . ?
C7 C6A H6AA 113.0 . . ?
C3B C6A H6AA 113.0 . . ?
O2 C6 C6A 104.1(7) . . ?
O2 C6 C5 100.7(8) . . ?
C6A C6 C5 106.8(9) . . ?
O2 C6 H6A 114.6 . . ?
C6A C6 H6A 114.6 . . ?
C5 C6 H6A 114.6 . . ?
O1 C7 C8 100.9(8) . . ?
O1 C7 C6A 101.9(7) . . ?
C8 C7 C6A 105.9(9) . . ?
O1 C7 H7A 115.4 . . ?
C8 C7 H7A 115.4 . . ?
C6A C7 H7A 115.4 . . ?
C9 C8 C7 107.2(9) . . ?
C9 C8 H8A 126.4 . . ?
C7 C8 H8A 126.4 . . ?
O1 C9A C9 101.6(7) . . ?
O1 C9A C1 111.5(7) . . ?
C9 C9A C1 123.0(7) . . ?
O1 C9A C3B 101.5(6) . . ?
C9 C9A C3B 105.0(7) . . ?
C1 C9A C3B 111.7(8) . . ?
C8 C9 C9A 105.1(9) . . ?
C8 C9 H9A 127.5 . . ?
C9A C9 H9A 127.5 . . ?
F1B C10 F3B 108.4(15) . . ?
F3A C10 F2A 111.1(11) . . ?
F1B C10 F2B 104.7(14) . . ?
F3B C10 F2B 99.3(12) . . ?
F3A C10 F1A 106.8(12) . . ?
F2A C10 F1A 97.6(10) . . ?
F3A C10 C4 114.0(12) . . ?
F1B C10 C4 121.6(15) . . ?
F3B C10 C4 112.1(13) . . ?
F2A C10 C4 113.7(10) . . ?
F2B C10 C4 108.1(15) . . ?
F1A C10 C4 112.3(9) . . ?
F4B C11 F6B 105.7(17) . . ?
F6A C11 F5A 109.0(11) . . ?
F6A C11 F4A 106.4(12) . . ?
F5A C11 F4A 100.9(11) . . ?
F4B C11 F5B 103.7(16) . . ?
F6B C11 F5B 101.1(15) . . ?
F6A C11 C5 116.6(11) . . ?
F4B C11 C5 124(2) . . ?
F6B C11 C5 114.0(19) . . ?
F5A C11 C5 109.4(11) . . ?
F4A C11 C5 113.4(11) . . ?
F5B C11 C5 104.9(19) . . ?
C13 C12 C17 121.7(11) . . ?
C13 C12 S1 119.4(8) . . ?
C17 C12 S1 118.9(8) . . ?
C12 C13 C14 119.3(10) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 118.4(11) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C14 C15 C16 123.0(11) . . ?
C14 C15 F7 119.1(12) . . ?
C16 C15 F7 117.9(11) . . ?
C15 C16 C17 122.0(12) . . ?
C15 C16 H16A 119.0 . . ?
C17 C16 H16A 119.0 . . ?
C16 C17 C12 115.6(12) . . ?
C16 C17 H17A 122.2 . . ?
C12 C17 H17A 122.2 . . ?

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
O4 S1 N2 C1 -170.2(7) . . . . ?
O3 S1 N2 C1 -40.9(8) . . . . ?
C12 S1 N2 C1 74.4(8) . . . . ?
O4 S1 N2 C3 46.2(8) . . . . ?
O3 S1 N2 C3 175.4(7) . . . . ?
C12 S1 N2 C3 -69.3(8) . . . . ?
C3 N2 C1 C9A -61.1(10) . . . . ?
S1 N2 C1 C9A 155.0(7) . . . . ?
C1 N2 C3 C3A 61.2(10) . . . . ?
S1 N2 C3 C3A -153.8(7) . . . . ?
C6 O2 C3A C3 -178.3(8) . . . . ?
C6 O2 C3A C3B -55.9(8) . . . . ?
C6 O2 C3A C4 53.7(8) . . . . ?
N2 C3 C3A O2 64.4(10) . . . . ?
N2 C3 C3A C3B -51.9(10) . . . . ?
N2 C3 C3A C4 -179.3(9) . . . . ?
C6A C3B C3A O2 33.3(8) . . . . ?
C9A C3B C3A O2 -74.3(8) . . . . ?
C6A C3B C3A C3 154.2(8) . . . . ?
C9A C3B C3A C3 46.6(10) . . . . ?
C6A C3B C3A C4 -71.5(9) . . . . ?
C9A C3B C3A C4 -179.2(8) . . . . ?
O2 C3A C4 C5 -35.3(10) . . . . ?
C3 C3A C4 C5 -157.4(9) . . . . ?
C3B C3A C4 C5 72.0(11) . . . . ?
O2 C3A C4 C10 152.5(9) . . . . ?
C3 C3A C4 C10 30.5(14) . . . . ?
C3B C3A C4 C10 -100.1(10) . . . . ?
C10 C4 C5 C11 2(2) . . . . ?
C3A C4 C5 C11 -169.6(12) . . . . ?
C10 C4 C5 C6 173.5(11) . . . . ?
C3A C4 C5 C6 1.9(12) . . . . ?
C3A C3B C6A C6 1.5(9) . . . . ?
C9A C3B C6A C6 118.7(8) . . . . ?
C3A C3B C6A C7 -118.1(8) . . . . ?
C9A C3B C6A C7 -0.8(9) . . . . ?
C3A O2 C6 C6A 57.7(8) . . . . ?
C3A O2 C6 C5 -52.8(8) . . . . ?
C7 C6A C6 O2 70.9(10) . . . . ?
C3B C6A C6 O2 -36.1(9) . . . . ?
C7 C6A C6 C5 176.9(8) . . . . ?
C3B C6A C6 C5 70.0(9) . . . . ?
C4 C5 C6 O2 32.2(11) . . . . ?
C11 C5 C6 O2 -155.4(11) . . . . ?
C4 C5 C6 C6A -76.3(11) . . . . ?
C11 C5 C6 C6A 96.1(12) . . . . ?
C9A O1 C7 C8 49.8(8) . . . . ?
C9A O1 C7 C6A -59.2(9) . . . . ?
C6 C6A C7 O1 -68.9(10) . . . . ?
C3B C6A C7 O1 36.4(9) . . . . ?
C6 C6A C7 C8 -174.1(8) . . . . ?
C3B C6A C7 C8 -68.8(9) . . . . ?
O1 C7 C8 C9 -32.6(10) . . . . ?
C6A C7 C8 C9 73.3(10) . . . . ?
C7 O1 C9A C9 -49.9(8) . . . . ?
C7 O1 C9A C1 177.3(7) . . . . ?
C7 O1 C9A C3B 58.2(8) . . . . ?
N2 C1 C9A O1 -62.3(9) . . . . ?
N2 C1 C9A C9 176.7(8) . . . . ?
N2 C1 C9A C3B 50.5(10) . . . . ?
C3A C3B C9A O1 73.7(8) . . . . ?
C6A C3B C9A O1 -34.8(8) . . . . ?
C3A C3B C9A C9 179.2(7) . . . . ?
C6A C3B C9A C9 70.7(8) . . . . ?
C3A C3B C9A C1 -45.3(10) . . . . ?
C6A C3B C9A C1 -153.8(7) . . . . ?
C7 C8 C9 C9A 0.5(11) . . . . ?
O1 C9A C9 C8 31.8(9) . . . . ?
C1 C9A C9 C8 157.2(9) . . . . ?
C3B C9A C9 C8 -73.6(9) . . . . ?
C5 C4 C10 F3A 96.4(16) . . . . ?
C3A C4 C10 F3A -93.5(15) . . . . ?
C5 C4 C10 F1B -82(2) . . . . ?
C3A C4 C10 F1B 88.5(18) . . . . ?
C5 C4 C10 F3B 147.8(16) . . . . ?
C3A C4 C10 F3B -42.0(17) . . . . ?
C5 C4 C10 F2A -32.4(17) . . . . ?
C3A C4 C10 F2A 137.8(11) . . . . ?
C5 C4 C10 F2B 39.4(18) . . . . ?
C3A C4 C10 F2B -150.4(14) . . . . ?
C5 C4 C10 F1A -142.0(13) . . . . ?
C3A C4 C10 F1A 28.1(14) . . . . ?
C4 C5 C11 F6A -49(2) . . . . ?
C6 C5 C11 F6A 141.2(13) . . . . ?
C4 C5 C11 F4B 142(2) . . . . ?
C6 C5 C11 F4B -29(3) . . . . ?
C4 C5 C11 F6B 10(2) . . . . ?
C6 C5 C11 F6B -160(2) . . . . ?
C4 C5 C11 F5A -172.9(13) . . . . ?
C6 C5 C11 F5A 17.0(16) . . . . ?
C4 C5 C11 F4A 75.4(17) . . . . ?
C6 C5 C11 F4A -94.8(15) . . . . ?
C4 C5 C11 F5B -100(2) . . . . ?
C6 C5 C11 F5B 90(2) . . . . ?
O4 S1 C12 C13 156.6(8) . . . . ?
O3 S1 C12 C13 24.9(10) . . . . ?
N2 S1 C12 C13 -89.0(9) . . . . ?
O4 S1 C12 C17 -25.5(10) . . . . ?
O3 S1 C12 C17 -157.1(9) . . . . ?
N2 S1 C12 C17 89.0(9) . . . . ?
C17 C12 C13 C14 -1.2(16) . . . . ?
S1 C12 C13 C14 176.7(8) . . . . ?
C12 C13 C14 C15 -1.2(16) . . . . ?
C13 C14 C15 C16 3.4(18) . . . . ?
C13 C14 C15 F7 -178.5(9) . . . . ?
C14 C15 C16 C17 -3(2) . . . . ?
F7 C15 C16 C17 178.7(11) . . . . ?
C15 C16 C17 C12 0.6(19) . . . . ?
C13 C12 C17 C16 1.5(17) . . . . ?
S1 C12 C17 C16 -176.4(10) . . . . ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.099


# start Validation Reply Form
_vrf_PLAT340_7b                  
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01505 Ang.
RESPONSE: Small crystal.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_8b
_database_code_depnum_ccdc_archive 'CCDC 2023805'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-10-21 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Cl F6 N O4 S'
_chemical_formula_sum            'C20 H14 Cl F6 N O4 S'
_chemical_formula_weight         513.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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'
Cl Cl 0.1750 0.1987 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0227 0.0132 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0148 0.0078 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1473 0.1546 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.8242(18)
_cell_length_b                   5.1860(7)
_cell_length_c                   14.912(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.717(18)
_cell_angle_gamma                90
_cell_volume                     977.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79313
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2713
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.546
_diffrn_reflns_theta_max         26.013
_diffrn_reflns_theta_full        28.417
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.778
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.778
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.767
_reflns_number_total             2713
_reflns_number_gt                2624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.753

_reflns_special_details          
;
 _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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+11.1P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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_abs_structure_details 
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.22(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2713
_refine_ls_number_parameters     346
_refine_ls_number_restraints     408
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0910
_refine_ls_wR_factor_ref         0.2223
_refine_ls_wR_factor_gt          0.2213
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      0.993
_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
Cl1 Cl 0.0918(3) 0.9913(9) 0.7779(3) 0.0388(12) Uani 1 1 d . U . . .
S1 S 0.4595(3) 0.1907(8) 0.8250(3) 0.0237(9) Uani 1 1 d . U . . .
F1 F 0.7081(9) 0.945(2) 0.5243(7) 0.050(3) Uani 1 1 d . U . . .
F2 F 0.6092(11) 0.632(3) 0.4700(8) 0.073(4) Uani 1 1 d . U . . .
F3 F 0.5712(9) 0.862(3) 0.5814(9) 0.072(4) Uani 1 1 d . U . . .
F4 F 0.848(3) 0.599(9) 0.4695(19) 0.044(6) Uani 0.46(2) 1 d D U P A 1
F5 F 0.9709(16) 0.574(6) 0.5864(15) 0.044(5) Uani 0.46(2) 1 d D U P A 1
F6 F 0.9065(18) 0.230(5) 0.5240(15) 0.047(5) Uani 0.46(2) 1 d D U P A 1
F4A F 0.840(3) 0.566(8) 0.4662(15) 0.058(10) Uani 0.54(2) 1 d D U P A 2
F5A F 0.9312(16) 0.782(4) 0.5757(13) 0.046(5) Uani 0.54(2) 1 d D U P A 2
F6A F 0.9597(17) 0.381(5) 0.5602(15) 0.051(6) Uani 0.54(2) 1 d D U P A 2
O1 O 0.4429(9) 0.007(2) 0.7544(7) 0.029(3) Uani 1 1 d . U . . .
O2 O 0.4797(9) 0.104(2) 0.9173(7) 0.028(3) Uani 1 1 d . U . . .
C1 C 0.6153(12) 0.522(3) 0.8826(10) 0.024(3) Uani 1 1 d . U . . .
H1A H 0.6062 0.4515 0.9426 0.029 Uiso 1 1 calc R U . . .
H1B H 0.5835 0.6959 0.8759 0.029 Uiso 1 1 calc R U . . .
N2 N 0.5639(11) 0.351(3) 0.8091(8) 0.025(3) Uani 1 1 d . U . . .
C3 C 0.5661(11) 0.450(4) 0.7158(10) 0.025(4) Uani 1 1 d . U . . .
H3A H 0.5321 0.6220 0.7078 0.030 Uiso 1 1 calc R U . . .
H3B H 0.5275 0.3315 0.6699 0.030 Uiso 1 1 calc R U . . .
C3A C 0.6805(13) 0.469(4) 0.7043(10) 0.027(4) Uani 1 1 d . U . . .
C4 C 0.7094(14) 0.567(4) 0.6140(11) 0.040(5) Uani 1 1 d D U . . .
C5 C 0.801(2) 0.446(9) 0.608(2) 0.041(6) Uani 0.46(2) 1 d D U P A 1
C5A C 0.808(2) 0.476(7) 0.6141(18) 0.033(6) Uani 0.54(2) 1 d D U P A 2
C6 C 0.8278(14) 0.307(4) 0.6967(11) 0.031(4) Uani 1 1 d D U . . .
H6 H 0.8800 0.1645 0.6954 0.037 Uiso 1 1 calc R U . A 1
C6A C 0.8592(13) 0.496(4) 0.7778(11) 0.034(4) Uani 1 1 d . U . . .
H6A H 0.9125 0.6268 0.7663 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8824(14) 0.383(4) 0.8735(11) 0.032(4) Uani 1 1 d . U . . .
H7 H 0.9391 0.2486 0.8816 0.039 Uiso 1 1 calc R U . . .
C8 C 0.9045(13) 0.604(3) 0.9375(10) 0.028(4) Uani 1 1 d . U . . .
H8 H 0.9709 0.6604 0.9695 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8118(12) 0.700(4) 0.9396(10) 0.030(4) Uani 1 1 d . U . . .
H9 H 0.7966 0.8455 0.9739 0.036 Uiso 1 1 calc R U . . .
C9A C 0.7301(12) 0.534(3) 0.8757(10) 0.022(3) Uani 1 1 d . U . . .
C9B C 0.7518(13) 0.609(3) 0.7785(10) 0.025(3) Uani 1 1 d . U . . .
H9B H 0.7506 0.7995 0.7687 0.030 Uiso 1 1 calc R U . . .
O10 O 0.7269(8) 0.219(2) 0.7060(7) 0.027(2) Uani 1 1 d . U . . .
O11 O 0.7830(8) 0.291(2) 0.8874(7) 0.022(2) Uani 1 1 d . U . . .
C10 C 0.3498(13) 0.413(3) 0.8132(10) 0.023(4) Uani 1 1 d . U . . .
C11 C 0.2944(13) 0.440(3) 0.7271(11) 0.025(4) Uani 1 1 d . U . . .
H11 H 0.3103 0.3432 0.6771 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2102(13) 0.627(4) 0.7176(12) 0.034(4) Uani 1 1 d . U . . .
H12 H 0.1686 0.6566 0.6596 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1897(13) 0.761(3) 0.7905(12) 0.029(4) Uani 1 1 d . U . . .
C14 C 0.2520(14) 0.729(4) 0.8778(12) 0.033(4) Uani 1 1 d . U . . .
H14 H 0.2399 0.8312 0.9279 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3302(12) 0.546(3) 0.8878(9) 0.019(3) Uani 1 1 d . U . . .
H15 H 0.3704 0.5113 0.9462 0.023 Uiso 1 1 calc R U . . .
C16 C 0.6497(14) 0.746(4) 0.5478(12) 0.040(5) Uani 1 1 d . U . . .
C17 C 0.879(2) 0.468(8) 0.546(2) 0.043(5) Uani 0.46(2) 1 d D U P A 1
C17A C 0.883(2) 0.557(7) 0.5537(18) 0.042(5) Uani 0.54(2) 1 d D U P A 2


_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
Cl1 C13 1.721(17) . ?
S1 O1 1.410(11) . ?
S1 O2 1.429(11) . ?
S1 N2 1.628(15) . ?
S1 C10 1.805(16) . ?
F1 C16 1.36(2) . ?
F2 C16 1.33(2) . ?
F3 C16 1.34(2) . ?
F4 C17 1.32(3) . ?
F5 C17 1.35(4) . ?
F6 C17 1.34(4) . ?
F4A C17A 1.33(3) . ?
F5A C17A 1.34(3) . ?
F6A C17A 1.34(4) . ?
C1 N2 1.47(2) . ?
C1 C9A 1.49(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C3 1.488(19) . ?
C3 C3A 1.51(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O10 1.43(2) . ?
C3A C9B 1.50(2) . ?
C3A C4 1.54(2) . ?
C4 C5 1.35(3) . ?
C4 C5A 1.35(3) . ?
C4 C16 1.47(3) . ?
C5 C17 1.48(3) . ?
C5 C6 1.50(3) . ?
C5A C17A 1.48(3) . ?
C5A C6 1.50(3) . ?
C6 O10 1.40(2) . ?
C6 C6A 1.55(2) . ?
C6 H6 1.0000 . ?
C6A C9B 1.50(2) . ?
C6A C7 1.52(2) . ?
C6A H6A 1.0000 . ?
C7 O11 1.41(2) . ?
C7 C8 1.49(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.29(2) . ?
C8 H8 0.9500 . ?
C9 C9A 1.55(2) . ?
C9 H9 0.9500 . ?
C9A O11 1.428(19) . ?
C9A C9B 1.57(2) . ?
C9B H9B 1.0000 . ?
C10 C11 1.37(2) . ?
C10 C15 1.37(2) . ?
C11 C12 1.44(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.35(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.42(2) . ?
C14 C15 1.37(2) . ?
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
O1 S1 O2 119.1(7) . . ?
O1 S1 N2 105.2(6) . . ?
O2 S1 N2 106.4(7) . . ?
O1 S1 C10 110.0(7) . . ?
O2 S1 C10 107.9(7) . . ?
N2 S1 C10 107.8(7) . . ?
N2 C1 C9A 107.2(13) . . ?
N2 C1 H1A 110.3 . . ?
C9A C1 H1A 110.3 . . ?
N2 C1 H1B 110.3 . . ?
C9A C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C1 N2 C3 114.3(13) . . ?
C1 N2 S1 118.3(10) . . ?
C3 N2 S1 117.3(11) . . ?
N2 C3 C3A 107.5(12) . . ?
N2 C3 H3A 110.2 . . ?
C3A C3 H3A 110.2 . . ?
N2 C3 H3B 110.2 . . ?
C3A C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O10 C3A C9B 103.0(12) . . ?
O10 C3A C3 110.4(15) . . ?
C9B C3A C3 115.6(14) . . ?
O10 C3A C4 98.8(13) . . ?
C9B C3A C4 106.2(15) . . ?
C3 C3A C4 120.2(14) . . ?
C5 C4 C16 127.5(18) . . ?
C5A C4 C16 127.0(17) . . ?
C5 C4 C3A 104.3(17) . . ?
C5A C4 C3A 104.3(16) . . ?
C16 C4 C3A 128.2(16) . . ?
C4 C5 C17 134(2) . . ?
C4 C5 C6 103.8(18) . . ?
C17 C5 C6 121(2) . . ?
C4 C5A C17A 127(2) . . ?
C4 C5A C6 103.6(16) . . ?
C17A C5A C6 129(2) . . ?
O10 C6 C5 99.4(17) . . ?
O10 C6 C5A 103.9(17) . . ?
O10 C6 C6A 104.5(13) . . ?
C5 C6 C6A 112(2) . . ?
C5A C6 C6A 105(2) . . ?
O10 C6 H6 113.2 . . ?
C5 C6 H6 113.2 . . ?
C6A C6 H6 113.2 . . ?
C9B C6A C7 100.3(13) . . ?
C9B C6A C6 97.7(13) . . ?
C7 C6A C6 118.2(17) . . ?
C9B C6A H6A 112.9 . . ?
C7 C6A H6A 112.9 . . ?
C6 C6A H6A 112.9 . . ?
O11 C7 C8 104.2(13) . . ?
O11 C7 C6A 103.2(13) . . ?
C8 C7 C6A 107.1(15) . . ?
O11 C7 H7 113.8 . . ?
C8 C7 H7 113.8 . . ?
C6A C7 H7 113.8 . . ?
C9 C8 C7 103.7(15) . . ?
C9 C8 H8 128.2 . . ?
C7 C8 H8 128.2 . . ?
C8 C9 C9A 107.4(16) . . ?
C8 C9 H9 126.3 . . ?
C9A C9 H9 126.3 . . ?
O11 C9A C1 113.9(13) . . ?
O11 C9A C9 99.0(12) . . ?
C1 C9A C9 123.5(14) . . ?
O11 C9A C9B 100.1(12) . . ?
C1 C9A C9B 113.9(13) . . ?
C9 C9A C9B 102.9(12) . . ?
C3A C9B C6A 104.7(14) . . ?
C3A C9B C9A 112.4(13) . . ?
C6A C9B C9A 102.5(13) . . ?
C3A C9B H9B 112.2 . . ?
C6A C9B H9B 112.2 . . ?
C9A C9B H9B 112.2 . . ?
C6 O10 C3A 95.2(13) . . ?
C7 O11 C9A 96.1(12) . . ?
C11 C10 C15 125.1(15) . . ?
C11 C10 S1 115.6(12) . . ?
C15 C10 S1 119.3(12) . . ?
C10 C11 C12 115.1(15) . . ?
C10 C11 H11 122.4 . . ?
C12 C11 H11 122.4 . . ?
C13 C12 C11 120.7(16) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.5(16) . . ?
C12 C13 Cl1 120.4(14) . . ?
C14 C13 Cl1 117.9(13) . . ?
C15 C14 C13 118.0(16) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C10 C15 C14 119.4(15) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F2 C16 F3 108.6(15) . . ?
F2 C16 F1 105.4(14) . . ?
F3 C16 F1 103.8(17) . . ?
F2 C16 C4 112.7(19) . . ?
F3 C16 C4 111.8(15) . . ?
F1 C16 C4 114.0(15) . . ?
F4 C17 F6 109(3) . . ?
F4 C17 F5 107(3) . . ?
F6 C17 F5 104(2) . . ?
F4 C17 C5 116(3) . . ?
F6 C17 C5 108(3) . . ?
F5 C17 C5 113(3) . . ?
F4A C17A F6A 106(3) . . ?
F4A C17A F5A 108(3) . . ?
F6A C17A F5A 106(2) . . ?
F4A C17A C5A 114(3) . . ?
F6A C17A C5A 108(2) . . ?
F5A C17A C5A 115(2) . . ?

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
C9A C1 N2 C3 -64.3(16) . . . . ?
C9A C1 N2 S1 151.1(11) . . . . ?
O1 S1 N2 C1 -167.3(11) . . . . ?
O2 S1 N2 C1 -40.1(13) . . . . ?
C10 S1 N2 C1 75.4(13) . . . . ?
O1 S1 N2 C3 49.2(13) . . . . ?
O2 S1 N2 C3 176.4(11) . . . . ?
C10 S1 N2 C3 -68.2(13) . . . . ?
C1 N2 C3 C3A 62.6(18) . . . . ?
S1 N2 C3 C3A -152.5(12) . . . . ?
N2 C3 C3A O10 66.1(16) . . . . ?
N2 C3 C3A C9B -50(2) . . . . ?
N2 C3 C3A C4 -180.0(16) . . . . ?
O10 C3A C4 C5 -30(3) . . . . ?
C9B C3A C4 C5 76(3) . . . . ?
C3 C3A C4 C5 -150(3) . . . . ?
O10 C3A C4 C5A -39(2) . . . . ?
C9B C3A C4 C5A 67(3) . . . . ?
C3 C3A C4 C5A -159(2) . . . . ?
O10 C3A C4 C16 148.1(19) . . . . ?
C9B C3A C4 C16 -105(2) . . . . ?
C3 C3A C4 C16 28(3) . . . . ?
C5A C4 C5 C17 -80(9) . . . . ?
C16 C4 C5 C17 10(7) . . . . ?
C3A C4 C5 C17 -172(5) . . . . ?
C5A C4 C5 C6 86(8) . . . . ?
C16 C4 C5 C6 176(2) . . . . ?
C3A C4 C5 C6 -6(3) . . . . ?
C5 C4 C5A C17A 103(9) . . . . ?
C16 C4 C5A C17A 7(5) . . . . ?
C3A C4 C5A C17A -166(3) . . . . ?
C5 C4 C5A C6 -84(8) . . . . ?
C16 C4 C5A C6 179(2) . . . . ?
C3A C4 C5A C6 6(3) . . . . ?
C4 C5 C6 O10 41(3) . . . . ?
C17 C5 C6 O10 -151(4) . . . . ?
C4 C5 C6 C5A -85(8) . . . . ?
C17 C5 C6 C5A 83(8) . . . . ?
C4 C5 C6 C6A -69(3) . . . . ?
C17 C5 C6 C6A 99(4) . . . . ?
C4 C5A C6 O10 29(3) . . . . ?
C17A C5A C6 O10 -159(3) . . . . ?
C4 C5A C6 C5 84(7) . . . . ?
C17A C5A C6 C5 -104(9) . . . . ?
C4 C5A C6 C6A -80(3) . . . . ?
C17A C5A C6 C6A 92(4) . . . . ?
O10 C6 C6A C9B -36.5(17) . . . . ?
C5 C6 C6A C9B 70.3(18) . . . . ?
C5A C6 C6A C9B 72.5(17) . . . . ?
O10 C6 C6A C7 69.6(18) . . . . ?
C5 C6 C6A C7 176.4(16) . . . . ?
C5A C6 C6A C7 178.6(15) . . . . ?
C9B C6A C7 O11 37.1(17) . . . . ?
C6 C6A C7 O11 -67.5(18) . . . . ?
C9B C6A C7 C8 -72.5(16) . . . . ?
C6 C6A C7 C8 -177.1(14) . . . . ?
O11 C7 C8 C9 -33.2(17) . . . . ?
C6A C7 C8 C9 75.6(17) . . . . ?
C7 C8 C9 C9A 0.3(17) . . . . ?
N2 C1 C9A O11 -61.6(16) . . . . ?
N2 C1 C9A C9 178.4(13) . . . . ?
N2 C1 C9A C9B 52.4(18) . . . . ?
C8 C9 C9A O11 31.5(16) . . . . ?
C8 C9 C9A C1 158.2(15) . . . . ?
C8 C9 C9A C9B -71.2(16) . . . . ?
O10 C3A C9B C6A 32.5(16) . . . . ?
C3 C3A C9B C6A 153.1(16) . . . . ?
C4 C3A C9B C6A -70.9(17) . . . . ?
O10 C3A C9B C9A -77.9(15) . . . . ?
C3 C3A C9B C9A 43(2) . . . . ?
C4 C3A C9B C9A 178.7(13) . . . . ?
C7 C6A C9B C3A -118.9(15) . . . . ?
C6 C6A C9B C3A 1.7(16) . . . . ?
C7 C6A C9B C9A -1.4(17) . . . . ?
C6 C6A C9B C9A 119.2(14) . . . . ?
O11 C9A C9B C3A 78.3(15) . . . . ?
C1 C9A C9B C3A -44(2) . . . . ?
C9 C9A C9B C3A -179.9(14) . . . . ?
O11 C9A C9B C6A -33.6(15) . . . . ?
C1 C9A C9B C6A -155.6(15) . . . . ?
C9 C9A C9B C6A 68.2(15) . . . . ?
C5 C6 O10 C3A -59(2) . . . . ?
C5A C6 O10 C3A -53.0(19) . . . . ?
C6A C6 O10 C3A 56.8(15) . . . . ?
C9B C3A O10 C6 -54.5(14) . . . . ?
C3 C3A O10 C6 -178.5(12) . . . . ?
C4 C3A O10 C6 54.6(14) . . . . ?
C8 C7 O11 C9A 52.1(14) . . . . ?
C6A C7 O11 C9A -59.6(15) . . . . ?
C1 C9A O11 C7 178.3(13) . . . . ?
C9 C9A O11 C7 -48.7(13) . . . . ?
C9B C9A O11 C7 56.3(13) . . . . ?
O1 S1 C10 C11 -24.9(15) . . . . ?
O2 S1 C10 C11 -156.3(13) . . . . ?
N2 S1 C10 C11 89.3(14) . . . . ?
O1 S1 C10 C15 157.1(12) . . . . ?
O2 S1 C10 C15 25.7(15) . . . . ?
N2 S1 C10 C15 -88.7(14) . . . . ?
C15 C10 C11 C12 1(2) . . . . ?
S1 C10 C11 C12 -177.2(12) . . . . ?
C10 C11 C12 C13 0(2) . . . . ?
C11 C12 C13 C14 2(3) . . . . ?
C11 C12 C13 Cl1 177.8(13) . . . . ?
C12 C13 C14 C15 -4(3) . . . . ?
Cl1 C13 C14 C15 -179.8(13) . . . . ?
C11 C10 C15 C14 -3(3) . . . . ?
S1 C10 C15 C14 175.2(13) . . . . ?
C13 C14 C15 C10 4(2) . . . . ?
C5 C4 C16 F2 67(4) . . . . ?
C5A C4 C16 F2 77(3) . . . . ?
C3A C4 C16 F2 -111(2) . . . . ?
C5 C4 C16 F3 -170(3) . . . . ?
C5A C4 C16 F3 -160(3) . . . . ?
C3A C4 C16 F3 12(3) . . . . ?
C5 C4 C16 F1 -53(4) . . . . ?
C5A C4 C16 F1 -43(4) . . . . ?
C3A C4 C16 F1 128.8(19) . . . . ?
C4 C5 C17 F4 -15(7) . . . . ?
C6 C5 C17 F4 -179(4) . . . . ?
C4 C5 C17 F6 -137(5) . . . . ?
C6 C5 C17 F6 59(5) . . . . ?
C4 C5 C17 F5 109(5) . . . . ?
C6 C5 C17 F5 -55(5) . . . . ?
C4 C5A C17A F4A -48(5) . . . . ?
C6 C5A C17A F4A 142(4) . . . . ?
C4 C5A C17A F6A -165(4) . . . . ?
C6 C5A C17A F6A 24(5) . . . . ?
C4 C5A C17A F5A 77(4) . . . . ?
C6 C5A C17A F5A -93(4) . . . . ?

_refine_diff_density_max         0.761
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 2023807'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-10-21 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Br F6 N O4 S'
_chemical_formula_sum            'C20 H14 Br F6 N O4 S'
_chemical_formula_weight         558.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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 -0.8805 2.8944 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0227 0.0132 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0148 0.0078 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1473 0.1546 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.111(3)
_cell_length_b                   5.1760(10)
_cell_length_c                   14.827(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.291(10)
_cell_angle_gamma                90
_cell_volume                     993.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.965
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79313
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7742
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.553
_diffrn_reflns_theta_max         30.981
_diffrn_reflns_theta_full        28.417
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4498
_reflns_number_gt                4256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.989

_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  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)+6P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.041(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4498
_refine_ls_number_parameters     345
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_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
Br1 Br 0.90919(6) 1.01335(17) 0.22266(6) 0.0321(3) Uani 1 1 d . . . . .
S1 S 0.53817(13) 0.1950(4) 0.17673(12) 0.0212(4) Uani 1 1 d . . . . .
F1 F 0.2917(4) 0.9515(10) 0.4802(4) 0.0368(13) Uani 1 1 d . . . . .
F2 F 0.4253(4) 0.8761(15) 0.4201(4) 0.0574(19) Uani 1 1 d . . . . .
F3 F 0.3901(6) 0.6397(13) 0.5306(4) 0.063(2) Uani 1 1 d . . . . .
F4 F 0.1512(15) 0.601(5) 0.5316(10) 0.041(3) Uani 0.504(15) 1 d D U P A 1
F5 F 0.0338(8) 0.589(3) 0.4128(7) 0.047(3) Uani 0.504(15) 1 d D U P A 1
F6 F 0.0923(9) 0.236(3) 0.4762(8) 0.047(3) Uani 0.504(15) 1 d D U P A 1
F4A F 0.1666(15) 0.576(4) 0.5380(11) 0.038(3) Uani 0.496(15) 1 d D U P A 2
F5A F 0.0786(9) 0.804(2) 0.4305(8) 0.041(3) Uani 0.496(15) 1 d D U P A 2
F6A F 0.0450(9) 0.393(3) 0.4433(8) 0.045(3) Uani 0.496(15) 1 d D U P A 2
O1 O 0.5579(3) 0.0164(13) 0.2499(3) 0.0235(10) Uani 1 1 d . . . . .
O2 O 0.5201(4) 0.1052(11) 0.0843(4) 0.0260(12) Uani 1 1 d . . . . .
C1 C 0.3858(5) 0.525(2) 0.1169(4) 0.0242(14) Uani 1 1 d . . . . .
H1A H 0.3948 0.4502 0.0573 0.029 Uiso 1 1 calc R U . . .
H1B H 0.4171 0.6997 0.1219 0.029 Uiso 1 1 calc R U . . .
N2 N 0.4363(5) 0.3590(13) 0.1924(4) 0.0209(13) Uani 1 1 d . . . . .
C3 C 0.4336(5) 0.4580(15) 0.2854(5) 0.0216(16) Uani 1 1 d . . . . .
H3A H 0.4667 0.6302 0.2931 0.026 Uiso 1 1 calc R U . . .
H3B H 0.4715 0.3395 0.3315 0.026 Uiso 1 1 calc R U . . .
C3A C 0.3210(5) 0.4767(15) 0.2979(5) 0.0190(14) Uani 1 1 d . . . . .
C4 C 0.2906(6) 0.5789(16) 0.3877(5) 0.0252(17) Uani 1 1 d D . . . .
C5 C 0.1996(14) 0.469(6) 0.3909(15) 0.035(4) Uani 0.504(15) 1 d D U P A 1
C5A C 0.1948(15) 0.491(6) 0.3873(16) 0.035(4) Uani 0.496(15) 1 d D U P A 2
C6 C 0.1718(6) 0.3126(17) 0.3037(5) 0.0267(17) Uani 1 1 d D . . . .
H6 H 0.1202 0.1714 0.3061 0.040 Uiso 1 1 d R U . A .
C6A C 0.1438(5) 0.502(2) 0.2231(5) 0.0259(14) Uani 1 1 d . . . . .
H6A H 0.0911 0.6334 0.2340 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1213(6) 0.3823(17) 0.1267(5) 0.0243(16) Uani 1 1 d . . . . .
H7 H 0.0660 0.2472 0.1183 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1045(6) 0.6046(16) 0.0598(5) 0.0255(16) Uani 1 1 d . . . . .
H8 H 0.0404 0.6606 0.0262 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1975(6) 0.7064(16) 0.0575(5) 0.0240(15) Uani 1 1 d . . . . .
H9 H 0.2139 0.8495 0.0223 0.029 Uiso 1 1 calc R U . . .
C9A C 0.2717(5) 0.5422(17) 0.1238(4) 0.0208(14) Uani 1 1 d . . . . .
C9B C 0.2511(5) 0.6218(16) 0.2206(5) 0.0220(15) Uani 1 1 d . . . . .
H9B H 0.2522 0.8132 0.2298 0.026 Uiso 1 1 calc R U . . .
O10 O 0.2732(4) 0.2252(11) 0.2947(3) 0.0237(11) Uani 1 1 d . . . . .
O11 O 0.2225(4) 0.2945(10) 0.1124(4) 0.0212(11) Uani 1 1 d . . . . .
C10 C 0.6435(6) 0.4138(16) 0.1885(5) 0.0228(15) Uani 1 1 d . . . . .
C11 C 0.7023(6) 0.4487(16) 0.2745(5) 0.0264(18) Uani 1 1 d . . . . .
H11 H 0.6878 0.3506 0.3251 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7818(6) 0.6265(17) 0.2859(5) 0.0264(16) Uani 1 1 d . . . . .
H12 H 0.8226 0.6542 0.3441 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8003(6) 0.7641(16) 0.2094(6) 0.0237(16) Uani 1 1 d . . . . .
C14 C 0.7435(6) 0.7298(17) 0.1229(5) 0.0256(16) Uani 1 1 d . . . . .
H14 H 0.7587 0.8255 0.0720 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6627(5) 0.5490(18) 0.1131(5) 0.0246(16) Uani 1 1 d . . . . .
H15 H 0.6218 0.5201 0.0551 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3495(7) 0.761(2) 0.4541(5) 0.035(2) Uani 1 1 d . . . . .
C17 C 0.1207(12) 0.480(5) 0.4538(10) 0.040(3) Uani 0.504(15) 1 d D U P A 1
C17A C 0.1217(13) 0.574(4) 0.4509(12) 0.038(3) Uani 0.496(15) 1 d D U P A 2


_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
Br1 C13 1.911(8) . ?
S1 O1 1.416(6) . ?
S1 O2 1.430(5) . ?
S1 N2 1.631(6) . ?
S1 C10 1.772(8) . ?
F1 C16 1.339(10) . ?
F2 C16 1.328(11) . ?
F3 C16 1.329(10) . ?
F4 C17 1.316(18) . ?
F5 C17 1.33(2) . ?
F6 C17 1.37(3) . ?
F4A C17A 1.331(18) . ?
F5A C17A 1.33(2) . ?
F6A C17A 1.36(3) . ?
C1 N2 1.481(10) . ?
C1 C9A 1.518(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C3 1.476(9) . ?
C3 C3A 1.520(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O10 1.443(9) . ?
C3A C9B 1.542(10) . ?
C3A C4 1.544(9) . ?
C4 C5 1.330(16) . ?
C4 C5A 1.336(17) . ?
C4 C16 1.485(12) . ?
C5 C17 1.501(16) . ?
C5 C6 1.519(17) . ?
C5A C17A 1.511(16) . ?
C5A C6 1.535(17) . ?
C6 O10 1.431(9) . ?
C6 C6A 1.545(12) . ?
C6 H6 0.9999 . ?
C6A C9B 1.542(10) . ?
C6A C7 1.543(10) . ?
C6A H6A 1.0000 . ?
C7 O11 1.451(9) . ?
C7 C8 1.512(11) . ?
C7 H7 1.0000 . ?
C8 C9 1.334(11) . ?
C8 H8 0.9500 . ?
C9 C9A 1.526(10) . ?
C9 H9 0.9500 . ?
C9A O11 1.433(10) . ?
C9A C9B 1.558(9) . ?
C9B H9B 1.0000 . ?
C10 C15 1.376(11) . ?
C10 C11 1.391(11) . ?
C11 C12 1.380(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(11) . ?
C14 C15 1.403(11) . ?
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
O1 S1 O2 120.2(4) . . ?
O1 S1 N2 106.4(3) . . ?
O2 S1 N2 107.1(3) . . ?
O1 S1 C10 107.4(3) . . ?
O2 S1 C10 107.9(3) . . ?
N2 S1 C10 107.2(4) . . ?
N2 C1 C9A 107.9(6) . . ?
N2 C1 H1A 110.1 . . ?
C9A C1 H1A 110.1 . . ?
N2 C1 H1B 110.1 . . ?
C9A C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C3 N2 C1 115.4(6) . . ?
C3 N2 S1 117.3(5) . . ?
C1 N2 S1 118.1(5) . . ?
N2 C3 C3A 107.8(5) . . ?
N2 C3 H3A 110.1 . . ?
C3A C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C3A C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
O10 C3A C3 111.3(6) . . ?
O10 C3A C9B 102.2(5) . . ?
C3 C3A C9B 114.4(6) . . ?
O10 C3A C4 99.6(5) . . ?
C3 C3A C4 121.2(6) . . ?
C9B C3A C4 105.6(6) . . ?
C5 C4 C16 128.4(9) . . ?
C5A C4 C16 127.4(9) . . ?
C5 C4 C3A 104.0(8) . . ?
C5A C4 C3A 104.6(9) . . ?
C16 C4 C3A 127.6(7) . . ?
C4 C5 C17 135.8(14) . . ?
C4 C5 C6 106.9(10) . . ?
C17 C5 C6 117.1(12) . . ?
C4 C5A C17A 126.2(15) . . ?
C4 C5A C6 105.8(10) . . ?
C17A C5A C6 127.8(14) . . ?
O10 C6 C5 98.6(10) . . ?
O10 C6 C5A 101.6(10) . . ?
O10 C6 C6A 103.7(6) . . ?
C5 C6 C6A 108.3(15) . . ?
C5A C6 C6A 103.5(15) . . ?
O10 C6 H6 114.6 . . ?
C5 C6 H6 115.4 . . ?
C5A C6 H6 117.1 . . ?
C6A C6 H6 114.6 . . ?
C9B C6A C6 99.8(6) . . ?
C9B C6A C7 100.3(5) . . ?
C6 C6A C7 116.5(8) . . ?
C9B C6A H6A 112.9 . . ?
C6 C6A H6A 112.9 . . ?
C7 C6A H6A 112.9 . . ?
O11 C7 C8 100.5(6) . . ?
O11 C7 C6A 102.6(5) . . ?
C8 C7 C6A 106.7(7) . . ?
O11 C7 H7 115.1 . . ?
C8 C7 H7 115.1 . . ?
C6A C7 H7 115.1 . . ?
C9 C8 C7 106.3(7) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
C8 C9 C9A 104.7(7) . . ?
C8 C9 H9 127.6 . . ?
C9A C9 H9 127.6 . . ?
O11 C9A C1 111.7(7) . . ?
O11 C9A C9 101.2(5) . . ?
C1 C9A C9 121.4(6) . . ?
O11 C9A C9B 101.8(5) . . ?
C1 C9A C9B 113.4(5) . . ?
C9 C9A C9B 105.0(6) . . ?
C3A C9B C6A 102.8(6) . . ?
C3A C9B C9A 112.7(6) . . ?
C6A C9B C9A 102.1(6) . . ?
C3A C9B H9B 112.8 . . ?
C6A C9B H9B 112.8 . . ?
C9A C9B H9B 112.8 . . ?
C6 O10 C3A 96.7(6) . . ?
C9A O11 C7 96.2(5) . . ?
C15 C10 C11 122.1(7) . . ?
C15 C10 S1 119.2(6) . . ?
C11 C10 S1 118.7(6) . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 117.9(7) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 123.3(7) . . ?
C14 C13 Br1 117.6(6) . . ?
C12 C13 Br1 119.1(6) . . ?
C13 C14 C15 117.7(7) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C10 C15 C14 119.3(7) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F2 C16 F3 108.3(8) . . ?
F2 C16 F1 105.7(8) . . ?
F3 C16 F1 105.6(7) . . ?
F2 C16 C4 112.0(7) . . ?
F3 C16 C4 111.1(9) . . ?
F1 C16 C4 113.7(7) . . ?
F4 C17 F5 108.5(19) . . ?
F4 C17 F6 106.3(17) . . ?
F5 C17 F6 104.8(14) . . ?
F4 C17 C5 114.9(15) . . ?
F5 C17 C5 111.0(17) . . ?
F6 C17 C5 111(2) . . ?
F4A C17A F5A 108.6(18) . . ?
F4A C17A F6A 106.8(17) . . ?
F5A C17A F6A 108.3(14) . . ?
F4A C17A C5A 112.4(17) . . ?
F5A C17A C5A 113.7(19) . . ?
F6A C17A C5A 106.7(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C3 -63.2(9) . . . . ?
C9A C1 N2 S1 150.9(6) . . . . ?
O1 S1 N2 C3 46.3(6) . . . . ?
O2 S1 N2 C3 176.1(5) . . . . ?
C10 S1 N2 C3 -68.4(6) . . . . ?
O1 S1 N2 C1 -168.4(6) . . . . ?
O2 S1 N2 C1 -38.6(7) . . . . ?
C10 S1 N2 C1 77.0(6) . . . . ?
C1 N2 C3 C3A 62.2(8) . . . . ?
S1 N2 C3 C3A -151.6(5) . . . . ?
N2 C3 C3A O10 64.7(7) . . . . ?
N2 C3 C3A C9B -50.6(8) . . . . ?
N2 C3 C3A C4 -178.9(7) . . . . ?
O10 C3A C4 C5 -31.8(17) . . . . ?
C3 C3A C4 C5 -154.0(17) . . . . ?
C9B C3A C4 C5 73.9(18) . . . . ?
O10 C3A C4 C5A -37.8(18) . . . . ?
C3 C3A C4 C5A -160.0(18) . . . . ?
C9B C3A C4 C5A 67.9(18) . . . . ?
O10 C3A C4 C16 148.9(8) . . . . ?
C3 C3A C4 C16 26.7(12) . . . . ?
C9B C3A C4 C16 -105.4(9) . . . . ?
C5A C4 C5 C17 -81(10) . . . . ?
C16 C4 C5 C17 2(5) . . . . ?
C3A C4 C5 C17 -177(3) . . . . ?
C5A C4 C5 C6 94(12) . . . . ?
C16 C4 C5 C6 176.9(11) . . . . ?
C3A C4 C5 C6 -2(2) . . . . ?
C5 C4 C5A C17A 107(13) . . . . ?
C16 C4 C5A C17A 5(4) . . . . ?
C3A C4 C5A C17A -168(3) . . . . ?
C5 C4 C5A C6 -79(10) . . . . ?
C16 C4 C5A C6 179.3(10) . . . . ?
C3A C4 C5A C6 6(2) . . . . ?
C4 C5 C6 O10 36(2) . . . . ?
C17 C5 C6 O10 -148(2) . . . . ?
C4 C5 C6 C5A -91(11) . . . . ?
C17 C5 C6 C5A 85(10) . . . . ?
C4 C5 C6 C6A -71(2) . . . . ?
C17 C5 C6 C6A 104(2) . . . . ?
C4 C5A C6 O10 28(2) . . . . ?
C17A C5A C6 O10 -158(3) . . . . ?
C4 C5A C6 C5 82(10) . . . . ?
C17A C5A C6 C5 -104(12) . . . . ?
C4 C5A C6 C6A -79(2) . . . . ?
C17A C5A C6 C6A 95(3) . . . . ?
O10 C6 C6A C9B -35.4(8) . . . . ?
C5 C6 C6A C9B 68.6(9) . . . . ?
C5A C6 C6A C9B 70.3(9) . . . . ?
O10 C6 C6A C7 71.4(7) . . . . ?
C5 C6 C6A C7 175.4(8) . . . . ?
C5A C6 C6A C7 177.1(8) . . . . ?
C9B C6A C7 O11 36.0(8) . . . . ?
C6 C6A C7 O11 -70.5(7) . . . . ?
C9B C6A C7 C8 -69.2(8) . . . . ?
C6 C6A C7 C8 -175.7(6) . . . . ?
O11 C7 C8 C9 -32.8(8) . . . . ?
C6A C7 C8 C9 73.9(7) . . . . ?
C7 C8 C9 C9A 0.2(8) . . . . ?
N2 C1 C9A O11 -62.6(7) . . . . ?
N2 C1 C9A C9 178.2(7) . . . . ?
N2 C1 C9A C9B 51.6(10) . . . . ?
C8 C9 C9A O11 33.0(7) . . . . ?
C8 C9 C9A C1 157.3(8) . . . . ?
C8 C9 C9A C9B -72.5(8) . . . . ?
O10 C3A C9B C6A 32.8(7) . . . . ?
C3 C3A C9B C6A 153.2(6) . . . . ?
C4 C3A C9B C6A -70.9(7) . . . . ?
O10 C3A C9B C9A -76.4(7) . . . . ?
C3 C3A C9B C9A 44.0(9) . . . . ?
C4 C3A C9B C9A 179.9(6) . . . . ?
C6 C6A C9B C3A 1.2(8) . . . . ?
C7 C6A C9B C3A -118.3(7) . . . . ?
C6 C6A C9B C9A 118.1(7) . . . . ?
C7 C6A C9B C9A -1.3(8) . . . . ?
O11 C9A C9B C3A 75.6(7) . . . . ?
C1 C9A C9B C3A -44.5(10) . . . . ?
C9 C9A C9B C3A -179.2(6) . . . . ?
O11 C9A C9B C6A -34.0(7) . . . . ?
C1 C9A C9B C6A -154.1(8) . . . . ?
C9 C9A C9B C6A 71.1(8) . . . . ?
C5 C6 O10 C3A -54.6(14) . . . . ?
C5A C6 O10 C3A -50.4(14) . . . . ?
C6A C6 O10 C3A 56.8(7) . . . . ?
C3 C3A O10 C6 -177.4(6) . . . . ?
C9B C3A O10 C6 -54.8(6) . . . . ?
C4 C3A O10 C6 53.6(6) . . . . ?
C1 C9A O11 C7 177.7(5) . . . . ?
C9 C9A O11 C7 -51.7(6) . . . . ?
C9B C9A O11 C7 56.4(6) . . . . ?
C8 C7 O11 C9A 51.5(6) . . . . ?
C6A C7 O11 C9A -58.4(7) . . . . ?
O1 S1 C10 C15 158.1(6) . . . . ?
O2 S1 C10 C15 27.2(7) . . . . ?
N2 S1 C10 C15 -87.9(7) . . . . ?
O1 S1 C10 C11 -23.7(7) . . . . ?
O2 S1 C10 C11 -154.6(6) . . . . ?
N2 S1 C10 C11 90.3(7) . . . . ?
C15 C10 C11 C12 1.0(12) . . . . ?
S1 C10 C11 C12 -177.2(6) . . . . ?
C10 C11 C12 C13 -0.4(12) . . . . ?
C11 C12 C13 C14 -0.4(12) . . . . ?
C11 C12 C13 Br1 179.7(6) . . . . ?
C12 C13 C14 C15 0.8(12) . . . . ?
Br1 C13 C14 C15 -179.3(6) . . . . ?
C11 C10 C15 C14 -0.7(12) . . . . ?
S1 C10 C15 C14 177.5(6) . . . . ?
C13 C14 C15 C10 -0.2(12) . . . . ?
C5 C4 C16 F2 -166(2) . . . . ?
C5A C4 C16 F2 -159(2) . . . . ?
C3A C4 C16 F2 13.1(13) . . . . ?
C5 C4 C16 F3 73(2) . . . . ?
C5A C4 C16 F3 80(2) . . . . ?
C3A C4 C16 F3 -108.2(9) . . . . ?
C5 C4 C16 F1 -46(2) . . . . ?
C5A C4 C16 F1 -39(2) . . . . ?
C3A C4 C16 F1 132.9(8) . . . . ?
C4 C5 C17 F4 -11(5) . . . . ?
C6 C5 C17 F4 175(2) . . . . ?
C4 C5 C17 F5 113(4) . . . . ?
C6 C5 C17 F5 -61(3) . . . . ?
C4 C5 C17 F6 -131(4) . . . . ?
C6 C5 C17 F6 55(3) . . . . ?
C4 C5A C17A F4A -48(4) . . . . ?
C6 C5A C17A F4A 139(3) . . . . ?
C4 C5A C17A F5A 76(3) . . . . ?
C6 C5A C17A F5A -97(3) . . . . ?
C4 C5A C17A F6A -165(3) . . . . ?
C6 C5A C17A F6A 22(4) . . . . ?

_refine_diff_density_max         0.829
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.121

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_10a
_database_code_depnum_ccdc_archive 'CCDC 2023808'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-10-27 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         'C20 H14 F6 I N O4 S'
_chemical_formula_sum            'C20 H14 F6 I N O4 S'
_chemical_formula_weight         605.28

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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                   12.3934(3)
_cell_length_b                   16.1660(4)
_cell_length_c                   10.9810(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.052(1)
_cell_angle_gamma                90
_cell_volume                     2114.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      29.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.695
_shelx_estimated_absorpt_T_min   0.484
_shelx_estimated_absorpt_T_max   0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_T_max  0.550
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28570
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6152
_reflns_number_gt                4816
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.0402P)²+2.5633P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         6152
_refine_ls_number_parameters     318
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.043
_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
I1 I 0.68825(2) 0.90683(2) 0.61534(3) 0.07796(12) Uani 1 1 d . . . . .
S1 S 0.24513(6) 0.68869(4) 0.63924(7) 0.04590(16) Uani 1 1 d . . . . .
F1A F 0.3705(2) 0.5302(2) 0.3169(3) 0.0879(11) Uani 0.892(5) 1 d . . P A 1
F2A F 0.3177(3) 0.40978(17) 0.2480(3) 0.0759(9) Uani 0.892(5) 1 d . . P A 1
F3A F 0.2401(2) 0.5148(2) 0.1463(2) 0.0674(7) Uani 0.892(5) 1 d . . P A 1
F4A F 0.0853(3) 0.38399(15) 0.1060(2) 0.0742(9) Uani 0.892(5) 1 d . . P A 1
F5A F 0.1473(3) 0.29124(17) 0.2426(3) 0.0863(10) Uani 0.892(5) 1 d . . P A 1
F6A F -0.0247(3) 0.3270(2) 0.1975(3) 0.0993(13) Uani 0.892(5) 1 d . . P A 1
F1B F 0.3605(12) 0.4324(9) 0.2975(18) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
F2B F 0.2202(14) 0.4720(12) 0.1419(10) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
F3B F 0.3191(15) 0.5618(6) 0.2674(17) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
F4B F 0.1779(9) 0.3240(12) 0.2129(16) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
F5B F 0.0301(14) 0.2914(8) 0.2644(16) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
F6B F 0.0177(13) 0.3713(11) 0.1055(10) 0.054(3) Uiso 0.108(5) 1 d D . P A 2
O1 O 0.03909(15) 0.54745(11) 0.38209(17) 0.0419(4) Uani 1 1 d . . . . .
O2 O 0.16626(16) 0.45107(11) 0.53712(17) 0.0433(4) Uani 1 1 d . . . . .
O3 O 0.14763(19) 0.73941(15) 0.5995(2) 0.0632(6) Uani 1 1 d . . . . .
O4 O 0.2696(2) 0.64611(15) 0.7577(2) 0.0604(6) Uani 1 1 d . . . . .
N2 N 0.23578(19) 0.61909(14) 0.5307(2) 0.0433(5) Uani 1 1 d . . . . .
C1 C 0.3145(2) 0.54907(18) 0.5574(3) 0.0458(6) Uani 1 1 d . . . . .
H1A H 0.338678 0.538635 0.647846 0.055 Uiso 1 1 calc R U . . .
H1B H 0.380225 0.562157 0.529443 0.055 Uiso 1 1 calc R U . . .
C3B C 0.1955(2) 0.48689(15) 0.3426(2) 0.0357(5) Uani 1 1 d . . . . .
C3A C 0.1254(2) 0.57028(15) 0.3264(2) 0.0373(5) Uani 1 1 d . . . . .
C3 C 0.1902(2) 0.64288(16) 0.3967(3) 0.0449(6) Uani 1 1 d . . . . .
H3A H 0.250852 0.657427 0.360694 0.054 Uiso 1 1 calc R U . . .
H3B H 0.141119 0.690428 0.389784 0.054 Uiso 1 1 calc R U . . .
C4 C 0.0585(2) 0.57850(18) 0.1873(3) 0.0466(6) Uani 1 1 d . . . . .
H4 H 0.071254 0.615098 0.127477 0.056 Uiso 1 1 calc R U . . .
C5 C -0.0212(2) 0.5225(2) 0.1709(3) 0.0513(7) Uani 1 1 d . . . . .
H5 H -0.076165 0.510710 0.096135 0.062 Uiso 1 1 calc R U . . .
C6A C 0.1000(2) 0.42073(15) 0.3231(2) 0.0399(5) Uani 1 1 d . . . . .
C6 C -0.0054(2) 0.48078(18) 0.2985(3) 0.0461(6) Uani 1 1 d . . . . .
H6 H -0.073372 0.455491 0.311159 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1305(3) 0.38036(17) 0.4588(3) 0.0489(6) Uani 1 1 d . . . . .
H7 H 0.069844 0.348559 0.477814 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2414(3) 0.33446(19) 0.4816(3) 0.0603(8) Uani 1 1 d . . . . .
H8 H 0.251550 0.277460 0.481530 0.072 Uiso 1 1 calc R U . . .
C9A C 0.2577(2) 0.47335(16) 0.4891(2) 0.0395(5) Uani 1 1 d . . . . .
C9 C 0.3201(3) 0.39125(19) 0.5014(3) 0.0545(7) Uani 1 1 d . . . . .
H9 H 0.397181 0.383120 0.519090 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2783(2) 0.48506(19) 0.2621(3) 0.0492(6) Uani 1 1 d D . . . .
C11 C 0.0795(3) 0.35518(19) 0.2195(3) 0.0543(7) Uani 1 1 d D . . . .
C12 C 0.3626(2) 0.74974(16) 0.6381(2) 0.0422(5) Uani 1 1 d . . . . .
C13 C 0.3492(3) 0.81499(18) 0.5543(3) 0.0520(7) Uani 1 1 d . . . . .
H13 H 0.278377 0.828541 0.502700 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4428(3) 0.86026(19) 0.5479(3) 0.0560(7) Uani 1 1 d . . . . .
H14 H 0.435046 0.904453 0.491919 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5470(3) 0.83935(17) 0.6248(3) 0.0498(6) Uani 1 1 d . . . . .
C16 C 0.5613(3) 0.77364(19) 0.7085(3) 0.0550(7) Uani 1 1 d . . . . .
H16 H 0.632387 0.760024 0.759478 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4682(2) 0.72846(18) 0.7154(3) 0.0509(6) Uani 1 1 d . . . . .
H17 H 0.476232 0.684192 0.771246 0.061 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
I1 C15 2.089(3) . ?
S1 O3 1.425(2) . ?
S1 O4 1.428(2) . ?
S1 N2 1.620(2) . ?
S1 C12 1.762(3) . ?
F1A C10 1.349(4) . ?
F2A C10 1.336(4) . ?
F3A C10 1.319(4) . ?
F4A C11 1.350(4) . ?
F5A C11 1.312(4) . ?
F6A C11 1.328(4) . ?
F1B C10 1.303(9) . ?
F2B C10 1.334(9) . ?
F3B C10 1.335(8) . ?
F4B C11 1.340(9) . ?
F5B C11 1.360(8) . ?
F6B C11 1.300(8) . ?
O1 C3A 1.420(3) . ?
O1 C6 1.424(3) . ?
O2 C9A 1.422(3) . ?
O2 C7 1.425(3) . ?
N2 C1 1.470(4) . ?
N2 C3 1.474(3) . ?
C1 C9A 1.504(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3B C10 1.528(3) . ?
C3B C6A 1.566(3) . ?
C3B C3A 1.587(3) . ?
C3B C9A 1.595(3) . ?
C3A C3 1.508(4) . ?
C3A C4 1.529(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.315(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.518(4) . ?
C5 H5 0.9300 . ?
C6A C11 1.524(4) . ?
C6A C7 1.574(4) . ?
C6A C6 1.590(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.521(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.313(5) . ?
C8 H8 0.9300 . ?
C9A C9 1.523(4) . ?
C9 H9 0.9300 . ?
C12 C13 1.379(4) . ?
C12 C17 1.392(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
O3 S1 O4 120.30(15) . . ?
O3 S1 N2 106.99(13) . . ?
O4 S1 N2 106.82(13) . . ?
O3 S1 C12 107.92(14) . . ?
O4 S1 C12 108.01(13) . . ?
N2 S1 C12 105.95(12) . . ?
C3A O1 C6 97.07(18) . . ?
C9A O2 C7 97.24(19) . . ?
C1 N2 C3 116.7(2) . . ?
C1 N2 S1 118.67(17) . . ?
C3 N2 S1 118.89(18) . . ?
N2 C1 C9A 109.5(2) . . ?
N2 C1 H1A 109.8 . . ?
C9A C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C9A C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C10 C3B C6A 120.7(2) . . ?
C10 C3B C3A 112.7(2) . . ?
C6A C3B C3A 101.24(19) . . ?
C10 C3B C9A 111.5(2) . . ?
C6A C3B C9A 100.38(19) . . ?
C3A C3B C9A 109.04(19) . . ?
O1 C3A C3 109.9(2) . . ?
O1 C3A C4 100.8(2) . . ?
C3 C3A C4 120.5(2) . . ?
O1 C3A C3B 100.70(18) . . ?
C3 C3A C3B 114.0(2) . . ?
C4 C3A C3B 108.3(2) . . ?
N2 C3 C3A 108.1(2) . . ?
N2 C3 H3A 110.1 . . ?
C3A C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C3A C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C3A 104.9(2) . . ?
C5 C4 H4 127.6 . . ?
C3A C4 H4 127.6 . . ?
C4 C5 C6 106.2(2) . . ?
C4 C5 H5 126.9 . . ?
C6 C5 H5 126.9 . . ?
C11 C6A C3B 122.7(2) . . ?
C11 C6A C7 111.4(2) . . ?
C3B C6A C7 100.3(2) . . ?
C11 C6A C6 109.8(2) . . ?
C3B C6A C6 99.26(19) . . ?
C7 C6A C6 112.6(2) . . ?
O1 C6 C5 100.8(2) . . ?
O1 C6 C6A 101.48(19) . . ?
C5 C6 C6A 108.5(2) . . ?
O1 C6 H6 114.8 . . ?
C5 C6 H6 114.8 . . ?
C6A C6 H6 114.8 . . ?
O2 C7 C8 100.2(2) . . ?
O2 C7 C6A 101.1(2) . . ?
C8 C7 C6A 109.1(2) . . ?
O2 C7 H7 114.9 . . ?
C8 C7 H7 114.9 . . ?
C6A C7 H7 114.9 . . ?
C9 C8 C7 106.4(3) . . ?
C9 C8 H8 126.8 . . ?
C7 C8 H8 126.8 . . ?
O2 C9A C1 109.4(2) . . ?
O2 C9A C9 100.6(2) . . ?
C1 C9A C9 120.6(2) . . ?
O2 C9A C3B 101.33(19) . . ?
C1 C9A C3B 114.8(2) . . ?
C9 C9A C3B 107.5(2) . . ?
C8 C9 C9A 105.0(3) . . ?
C8 C9 H9 127.5 . . ?
C9A C9 H9 127.5 . . ?
F1B C10 F2B 110.8(9) . . ?
F1B C10 F3B 109.8(9) . . ?
F2B C10 F3B 106.5(9) . . ?
F3A C10 F2A 105.4(3) . . ?
F3A C10 F1A 105.5(3) . . ?
F2A C10 F1A 104.6(3) . . ?
F1B C10 C3B 115.8(9) . . ?
F3A C10 C3B 115.6(2) . . ?
F2B C10 C3B 108.1(9) . . ?
F3B C10 C3B 105.3(8) . . ?
F2A C10 C3B 114.2(2) . . ?
F1A C10 C3B 110.6(2) . . ?
F5A C11 F6A 107.7(3) . . ?
F6B C11 F4B 109.0(9) . . ?
F5A C11 F4A 104.8(3) . . ?
F6A C11 F4A 104.4(3) . . ?
F6B C11 F5B 107.3(9) . . ?
F4B C11 F5B 104.0(8) . . ?
F6B C11 C6A 120.8(8) . . ?
F5A C11 C6A 116.0(3) . . ?
F6A C11 C6A 109.1(3) . . ?
F4B C11 C6A 109.6(8) . . ?
F4A C11 C6A 114.1(2) . . ?
F5B C11 C6A 104.8(8) . . ?
C13 C12 C17 121.0(3) . . ?
C13 C12 S1 119.1(2) . . ?
C17 C12 S1 119.8(2) . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 I1 119.9(2) . . ?
C16 C15 I1 118.6(2) . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C12 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?

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
O3 S1 N2 C1 -169.0(2) . . . . ?
O4 S1 N2 C1 -38.9(2) . . . . ?
C12 S1 N2 C1 76.1(2) . . . . ?
O3 S1 N2 C3 38.5(2) . . . . ?
O4 S1 N2 C3 168.5(2) . . . . ?
C12 S1 N2 C3 -76.5(2) . . . . ?
C3 N2 C1 C9A -59.1(3) . . . . ?
S1 N2 C1 C9A 147.80(19) . . . . ?
C6 O1 C3A C3 179.7(2) . . . . ?
C6 O1 C3A C4 51.5(2) . . . . ?
C6 O1 C3A C3B -59.8(2) . . . . ?
C10 C3B C3A O1 165.7(2) . . . . ?
C6A C3B C3A O1 35.3(2) . . . . ?
C9A C3B C3A O1 -69.9(2) . . . . ?
C10 C3B C3A C3 -76.8(3) . . . . ?
C6A C3B C3A C3 152.9(2) . . . . ?
C9A C3B C3A C3 47.7(3) . . . . ?
C10 C3B C3A C4 60.4(3) . . . . ?
C6A C3B C3A C4 -69.9(2) . . . . ?
C9A C3B C3A C4 -175.2(2) . . . . ?
C1 N2 C3 C3A 61.3(3) . . . . ?
S1 N2 C3 C3A -145.6(2) . . . . ?
O1 C3A C3 N2 57.8(3) . . . . ?
C4 C3A C3 N2 174.2(2) . . . . ?
C3B C3A C3 N2 -54.4(3) . . . . ?
O1 C3A C4 C5 -33.2(3) . . . . ?
C3 C3A C4 C5 -154.2(3) . . . . ?
C3B C3A C4 C5 72.0(3) . . . . ?
C3A C4 C5 C6 0.9(3) . . . . ?
C10 C3B C6A C11 -3.9(4) . . . . ?
C3A C3B C6A C11 121.3(3) . . . . ?
C9A C3B C6A C11 -126.7(3) . . . . ?
C10 C3B C6A C7 120.1(2) . . . . ?
C3A C3B C6A C7 -114.7(2) . . . . ?
C9A C3B C6A C7 -2.7(2) . . . . ?
C10 C3B C6A C6 -124.7(2) . . . . ?
C3A C3B C6A C6 0.5(2) . . . . ?
C9A C3B C6A C6 112.5(2) . . . . ?
C3A O1 C6 C5 -50.8(2) . . . . ?
C3A O1 C6 C6A 60.8(2) . . . . ?
C4 C5 C6 O1 31.5(3) . . . . ?
C4 C5 C6 C6A -74.6(3) . . . . ?
C11 C6A C6 O1 -166.0(2) . . . . ?
C3B C6A C6 O1 -36.2(2) . . . . ?
C7 C6A C6 O1 69.2(3) . . . . ?
C11 C6A C6 C5 -60.4(3) . . . . ?
C3B C6A C6 C5 69.4(2) . . . . ?
C7 C6A C6 C5 174.8(2) . . . . ?
C9A O2 C7 C8 51.0(2) . . . . ?
C9A O2 C7 C6A -61.0(2) . . . . ?
C11 C6A C7 O2 169.4(2) . . . . ?
C3B C6A C7 O2 37.9(2) . . . . ?
C6 C6A C7 O2 -66.7(3) . . . . ?
C11 C6A C7 C8 64.4(3) . . . . ?
C3B C6A C7 C8 -67.0(3) . . . . ?
C6 C6A C7 C8 -171.7(2) . . . . ?
O2 C7 C8 C9 -31.7(3) . . . . ?
C6A C7 C8 C9 73.8(3) . . . . ?
C7 O2 C9A C1 -179.7(2) . . . . ?
C7 O2 C9A C9 -51.8(2) . . . . ?
C7 O2 C9A C3B 58.7(2) . . . . ?
N2 C1 C9A O2 -63.6(3) . . . . ?
N2 C1 C9A C9 -179.4(2) . . . . ?
N2 C1 C9A C3B 49.5(3) . . . . ?
C10 C3B C9A O2 -162.2(2) . . . . ?
C6A C3B C9A O2 -33.1(2) . . . . ?
C3A C3B C9A O2 72.7(2) . . . . ?
C10 C3B C9A C1 80.0(3) . . . . ?
C6A C3B C9A C1 -150.9(2) . . . . ?
C3A C3B C9A C1 -45.1(3) . . . . ?
C10 C3B C9A C9 -57.1(3) . . . . ?
C6A C3B C9A C9 71.9(2) . . . . ?
C3A C3B C9A C9 177.8(2) . . . . ?
C7 C8 C9 C9A -0.7(3) . . . . ?
O2 C9A C9 C8 33.2(3) . . . . ?
C1 C9A C9 C8 153.4(3) . . . . ?
C3B C9A C9 C8 -72.4(3) . . . . ?
C6A C3B C10 F1B -80.5(9) . . . . ?
C3A C3B C10 F1B 159.9(9) . . . . ?
C9A C3B C10 F1B 36.8(9) . . . . ?
C6A C3B C10 F3A 78.2(3) . . . . ?
C3A C3B C10 F3A -41.4(3) . . . . ?
C9A C3B C10 F3A -164.5(3) . . . . ?
C6A C3B C10 F2B 44.5(9) . . . . ?
C3A C3B C10 F2B -75.1(9) . . . . ?
C9A C3B C10 F2B 161.8(9) . . . . ?
C6A C3B C10 F3B 158.1(8) . . . . ?
C3A C3B C10 F3B 38.5(9) . . . . ?
C9A C3B C10 F3B -84.6(8) . . . . ?
C6A C3B C10 F2A -44.4(4) . . . . ?
C3A C3B C10 F2A -164.0(3) . . . . ?
C9A C3B C10 F2A 72.9(3) . . . . ?
C6A C3B C10 F1A -162.1(3) . . . . ?
C3A C3B C10 F1A 78.3(3) . . . . ?
C9A C3B C10 F1A -44.7(3) . . . . ?
C3B C6A C11 F6B -85.2(10) . . . . ?
C7 C6A C11 F6B 156.0(9) . . . . ?
C6 C6A C11 F6B 30.5(10) . . . . ?
C3B C6A C11 F5A 79.0(4) . . . . ?
C7 C6A C11 F5A -39.8(4) . . . . ?
C6 C6A C11 F5A -165.3(3) . . . . ?
C3B C6A C11 F6A -159.3(3) . . . . ?
C7 C6A C11 F6A 82.0(4) . . . . ?
C6 C6A C11 F6A -43.5(4) . . . . ?
C3B C6A C11 F4B 42.7(9) . . . . ?
C7 C6A C11 F4B -76.0(9) . . . . ?
C6 C6A C11 F4B 158.5(8) . . . . ?
C3B C6A C11 F4A -43.0(4) . . . . ?
C7 C6A C11 F4A -161.7(3) . . . . ?
C6 C6A C11 F4A 72.8(3) . . . . ?
C3B C6A C11 F5B 153.8(8) . . . . ?
C7 C6A C11 F5B 35.0(8) . . . . ?
C6 C6A C11 F5B -90.5(8) . . . . ?
O3 S1 C12 C13 -28.7(3) . . . . ?
O4 S1 C12 C13 -160.2(2) . . . . ?
N2 S1 C12 C13 85.6(2) . . . . ?
O3 S1 C12 C17 155.4(2) . . . . ?
O4 S1 C12 C17 23.9(3) . . . . ?
N2 S1 C12 C17 -90.3(2) . . . . ?
C17 C12 C13 C14 -0.4(4) . . . . ?
S1 C12 C13 C14 -176.3(2) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C13 C14 C15 I1 179.8(2) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
I1 C15 C16 C17 -179.9(2) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
C13 C12 C17 C16 0.3(5) . . . . ?
S1 C12 C17 C16 176.1(2) . . . . ?

_refine_diff_density_max         1.563
_refine_diff_density_min         -1.693
_refine_diff_density_rms         0.070


# start Validation Reply Form
_vrf_PLAT910_10a                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 17 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
