# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_KM11201
_database_code_depnum_ccdc_archive 'CCDC 1988907'
loop_
_audit_author_name
_audit_author_address
' Minyaev Mikhail'
;Zelinsky Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-07-08 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         'C17 H12 F6 N2 O S'
_chemical_formula_sum            'C17 H12 F6 N2 O S'
_chemical_formula_weight         406.35

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.1213(2)
_cell_length_b                   9.6599(3)
_cell_length_c                   24.5371(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1687.93(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      32.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.264
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_T_max  0.6843
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            59793
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.684
_diffrn_reflns_theta_max         33.208
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6462
_reflns_number_gt                5749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

 Refined as a 2-component inversion 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)+(0.0325P)²+0.3413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Crystalized from the racemic mixture.
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6462
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.78489(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 . . . . .


_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 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_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_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) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049

