#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:26:04 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255996 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126853.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7126853
loop_
_publ_author_name
'Kosobokov, Mikhail D.'
'Zubkov, Mikhail O.'
'Levin, Vitalij V.'
'Kokorekin, Vladimir A.'
'Dilman, Alexander D.'
_publ_section_title
;
 Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene
 difunctionalization.
;
_journal_issue                   66
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9453
_journal_page_last               9456
_journal_paper_doi               10.1039/d0cc04617e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H12 F6 N2 O S'
_chemical_formula_sum            'C17 H12 F6 N2 O S'
_chemical_formula_weight         406.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-07 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1213(2)
_cell_length_b                   9.6599(3)
_cell_length_c                   24.5371(8)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.79
_cell_measurement_theta_min      2.68
_cell_volume                     1687.93(9)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            59793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.208
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.6843
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Crystalized from the racemic mixture.
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         6462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0325P)²+0.3413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5749
_reflns_number_total             6462
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04617e2.cif
_cod_data_source_block           KM11201
_cod_depositor_comments          'Adding full bibliography for 7126853.cif.'
_cod_database_code               7126853
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.966
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'
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 0.78489(6) 0.33738(4) 0.65109(2) 0.01829(8) Uani 1 1 d . . . . .
F1 F 0.99073(19) 0.05138(14) 0.52281(6) 0.0394(3) Uani 1 1 d . . . . .
F2 F 0.8468(2) 0.24072(15) 0.49781(5) 0.0337(3) Uani 1 1 d . . . . .
F3 F 0.63994(17) 0.54849(13) 0.73122(4) 0.0259(2) Uani 1 1 d . . . . .
F4 F 0.56602(18) 0.81632(13) 0.71031(5) 0.0293(3) Uani 1 1 d . . . . .
F5 F 0.7111(2) 0.76953(12) 0.53283(5) 0.0354(3) Uani 1 1 d . . . . .
F6 F 0.80906(17) 0.50312(12) 0.54565(4) 0.0241(2) Uani 1 1 d . . . . .
O1 O 0.29063(19) 0.39771(13) 0.61722(5) 0.0192(2) Uani 1 1 d . . . . .
N1 N 0.0096(3) 1.03757(18) 0.68455(7) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.6365(2) 0.79106(16) 0.62159(7) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.0593(3) 0.9284(2) 0.67291(8) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.1173(2) 0.79055(18) 0.65910(7) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.1293(2) 0.69068(19) 0.69977(7) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.098803 0.714283 0.736300 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1853(2) 0.55726(18) 0.68742(7) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.193278 0.489076 0.715229 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2301(2) 0.52392(17) 0.63354(7) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.2159(3) 0.62334(18) 0.59247(7) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.244514 0.599249 0.555863 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1606(2) 0.75625(19) 0.60488(7) 0.0200(3) Uani 1 1 d . . . . .
H7 H 0.151697 0.824193 0.577007 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3391(3) 0.29846(18) 0.65858(7) 0.0193(3) Uani 1 1 d . . . . .
H8A H 0.224256 0.257170 0.674482 0.023 Uiso 1 1 calc R U . . .
H8B H 0.411561 0.343480 0.688096 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4559(2) 0.18863(18) 0.63110(7) 0.0190(3) Uani 1 1 d . . . . .
H9A H 0.376957 0.139887 0.604002 0.023 Uiso 1 1 calc R U . . .
H9B H 0.495395 0.119956 0.658774 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6308(2) 0.24467(17) 0.60242(7) 0.0163(3) Uani 1 1 d . . . . .
H10 H 0.590683 0.310621 0.573238 0.020 Uiso 1 1 calc R U . . .
C11 C 0.7388(3) 0.12557(18) 0.57622(7) 0.0205(3) Uani 1 1 d . . . . .
H11A H 0.782592 0.062573 0.605397 0.025 Uiso 1 1 calc R U . . .
H11B H 0.651434 0.072627 0.552755 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9046(3) 0.1680(2) 0.54268(8) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.999(4) 0.224(3) 0.5619(10) 0.029(6) Uiso 1 1 d . . . . .
C13 C 0.7221(2) 0.51106(17) 0.63881(6) 0.0163(3) Uani 1 1 d . . . . .
C14 C 0.6616(2) 0.59678(18) 0.68051(7) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.6224(3) 0.73435(19) 0.66975(8) 0.0202(3) Uani 1 1 d . . . . .
C16 C 0.6941(3) 0.71104(19) 0.58183(7) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.7412(2) 0.57355(18) 0.58810(7) 0.0186(3) Uani 1 1 d . . . . .
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'
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
C13 S1 C10 101.52(8) . . ?
C5 O1 C8 117.90(13) . . ?
C15 N2 C16 116.76(16) . . ?
N1 C1 C2 178.5(2) . . ?
C3 C2 C7 120.16(16) . . ?
C3 C2 C1 119.48(16) . . ?
C7 C2 C1 120.37(16) . . ?
C4 C3 C2 120.47(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.20(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
O1 C5 C6 115.41(14) . . ?
O1 C5 C4 124.06(15) . . ?
C6 C5 C4 120.53(15) . . ?
C7 C6 C5 120.17(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.46(17) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O1 C8 C9 106.62(14) . . ?
O1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 C10 113.96(14) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 109.72(14) . . ?
C11 C10 S1 109.71(12) . . ?
C9 C10 S1 110.90(12) . . ?
C11 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
S1 C10 H10 108.8 . . ?
C12 C11 C10 115.02(15) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
F2 C12 F1 105.65(16) . . ?
F2 C12 C11 110.22(16) . . ?
F1 C12 C11 108.86(16) . . ?
F2 C12 H12 108.0(15) . . ?
F1 C12 H12 108.4(15) . . ?
C11 C12 H12 115.3(15) . . ?
C14 C13 C17 115.60(15) . . ?
C14 C13 S1 121.45(13) . . ?
C17 C13 S1 122.82(13) . . ?
F3 C14 C15 119.28(16) . . ?
F3 C14 C13 120.97(16) . . ?
C15 C14 C13 119.76(16) . . ?
N2 C15 F4 116.70(16) . . ?
N2 C15 C14 124.03(17) . . ?
F4 C15 C14 119.27(17) . . ?
N2 C16 F5 116.71(16) . . ?
N2 C16 C17 124.15(17) . . ?
F5 C16 C17 119.13(17) . . ?
F6 C17 C16 119.48(16) . . ?
F6 C17 C13 120.84(15) . . ?
C16 C17 C13 119.66(16) . . ?
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 C13 1.7622(17) . ?
S1 C10 1.8529(17) . ?
F1 C12 1.372(2) . ?
F2 C12 1.369(2) . ?
F3 C14 1.338(2) . ?
F4 C15 1.333(2) . ?
F5 C16 1.334(2) . ?
F6 C17 1.335(2) . ?
O1 C5 1.354(2) . ?
O1 C8 1.438(2) . ?
N1 C1 1.149(3) . ?
N2 C15 1.307(2) . ?
N2 C16 1.311(2) . ?
C1 C2 1.435(3) . ?
C2 C3 1.391(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.507(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.496(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.98(3) . ?
C13 C14 1.385(2) . ?
C13 C17 1.390(2) . ?
C14 C15 1.383(3) . ?
C16 C17 1.378(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
C7 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 C4 -179.84(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C8 O1 C5 C6 169.47(15) . . . . ?
C8 O1 C5 C4 -9.9(2) . . . . ?
C3 C4 C5 O1 178.37(16) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
O1 C5 C6 C7 -178.25(16) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C1 C2 C7 C6 -179.98(17) . . . . ?
C5 O1 C8 C9 -162.59(14) . . . . ?
O1 C8 C9 C10 56.64(19) . . . . ?
C8 C9 C10 C11 179.84(15) . . . . ?
C8 C9 C10 S1 58.48(17) . . . . ?
C13 S1 C10 C11 139.96(12) . . . . ?
C13 S1 C10 C9 -98.67(12) . . . . ?
C9 C10 C11 C12 174.98(15) . . . . ?
S1 C10 C11 C12 -62.95(18) . . . . ?
C10 C11 C12 F2 -66.0(2) . . . . ?
C10 C11 C12 F1 178.55(15) . . . . ?
C10 S1 C13 C14 124.76(15) . . . . ?
C10 S1 C13 C17 -59.51(16) . . . . ?
C17 C13 C14 F3 -179.33(15) . . . . ?
S1 C13 C14 F3 -3.3(2) . . . . ?
C17 C13 C14 C15 0.8(2) . . . . ?
S1 C13 C14 C15 176.86(14) . . . . ?
C16 N2 C15 F4 179.18(16) . . . . ?
C16 N2 C15 C14 -0.9(3) . . . . ?
F3 C14 C15 N2 -179.04(16) . . . . ?
C13 C14 C15 N2 0.8(3) . . . . ?
F3 C14 C15 F4 0.8(3) . . . . ?
C13 C14 C15 F4 -179.32(16) . . . . ?
C15 N2 C16 F5 -179.09(17) . . . . ?
C15 N2 C16 C17 -0.6(3) . . . . ?
N2 C16 C17 F6 -176.00(17) . . . . ?
F5 C16 C17 F6 2.4(3) . . . . ?
N2 C16 C17 C13 2.3(3) . . . . ?
F5 C16 C17 C13 -179.29(16) . . . . ?
C14 C13 C17 F6 176.01(15) . . . . ?
S1 C13 C17 F6 0.1(2) . . . . ?
C14 C13 C17 C16 -2.2(2) . . . . ?
S1 C13 C17 C16 -178.19(14) . . . . ?
