# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_adil
_database_code_depnum_ccdc_archive 'CCDC 1947115'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
loop_
_audit_author_email
alex@xrlab.ineos.ac.ru
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 F6 N S'
_chemical_formula_sum            'C13 H7 F6 N S'
_chemical_formula_weight         323.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5947(11)
_cell_length_b                   4.8799(6)
_cell_length_c                   13.6316(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.414(2)
_cell_angle_gamma                90
_cell_volume                     636.35(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3930
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.69
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0874 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.9035. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9856
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.776
_diffrn_reflns_theta_min         2.129
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4107
_reflns_number_total             4591
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.64176(5) 0.85452(10) 0.32506(3) 0.02137(10) Uani 1 1 d . . . . .
F1 F 0.89087(13) 0.5698(3) 0.24522(8) 0.0297(3) Uani 1 1 d . . . . .
F2 F 1.03565(13) 0.1462(3) 0.33060(10) 0.0370(3) Uani 1 1 d . . . . .
F3 F 0.78104(16) 0.1587(3) 0.59456(9) 0.0424(4) Uani 1 1 d . . . . .
F4 F 0.62020(14) 0.5776(3) 0.52142(9) 0.0357(3) Uani 1 1 d . . . . .
F5 F 0.59370(12) 0.4927(2) 0.18440(8) 0.0255(3) Uani 1 1 d . . . . .
F6 F 0.46468(12) 0.4465(2) 0.30627(9) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.90593(18) 0.1560(4) 0.46136(12) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.74673(19) 0.5877(4) 0.37872(12) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.85689(19) 0.4755(4) 0.33208(13) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.9314(2) 0.2594(4) 0.37609(15) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.8045(2) 0.2656(4) 0.50714(14) 0.0269(4) Uani 1 1 d . . . . .
C5 C 0.7221(2) 0.4793(4) 0.47040(13) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.52098(18) 0.6399(4) 0.24850(13) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.4085(2) 0.8142(4) 0.19526(13) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.4519 0.9607 0.1604 0.024 Uiso 1 1 calc R . . . .
H7B H 0.3512 0.8967 0.2429 0.024 Uiso 1 1 calc R . . . .
C8 C 0.31656(19) 0.6454(4) 0.12280(13) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.3343(2) 0.6585(5) 0.02226(14) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.4012 0.7750 -0.0008 0.029 Uiso 1 1 calc R . . . .
C10 C 0.2521(2) 0.4980(5) -0.04349(14) 0.0285(4) Uani 1 1 d . . . . .
H10 H 0.2643 0.5080 -0.1104 0.034 Uiso 1 1 calc R . . . .
C11 C 0.1525(2) 0.3236(5) -0.01045(14) 0.0272(4) Uani 1 1 d . . . . .
H11 H 0.0986 0.2149 -0.0547 0.033 Uiso 1 1 calc R . . . .
C12 C 0.1334(2) 0.3117(5) 0.08973(15) 0.0273(4) Uani 1 1 d . . . . .
H12 H 0.0661 0.1957 0.1124 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2144(2) 0.4721(4) 0.15562(14) 0.0225(4) Uani 1 1 d . . . . .
H13 H 0.2006 0.4642 0.2223 0.027 Uiso 1 1 calc R . . . .


_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 C1 1.7695(19) . ?
S1 C6 1.8284(18) . ?
F1 C2 1.334(2) . ?
F2 C3 1.336(2) . ?
F3 C4 1.336(2) . ?
F4 C5 1.332(2) . ?
F5 C6 1.364(2) . ?
F6 C6 1.367(2) . ?
N1 C3 1.307(3) . ?
N1 C4 1.310(3) . ?
C1 C2 1.387(3) . ?
C1 C5 1.394(3) . ?
C2 C3 1.385(3) . ?
C4 C5 1.379(3) . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(2) . ?
C8 C9 1.395(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 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
C1 S1 C6 97.47(9) . . ?
C3 N1 C4 117.57(18) . . ?
C2 C1 S1 122.04(14) . . ?
C2 C1 C5 116.67(17) . . ?
C5 C1 S1 121.29(15) . . ?
F1 C2 C1 121.16(16) . . ?
F1 C2 C3 119.59(18) . . ?
C3 C2 C1 119.25(18) . . ?
F2 C3 C2 119.60(18) . . ?
N1 C3 F2 116.82(18) . . ?
N1 C3 C2 123.6(2) . . ?
F3 C4 C5 119.2(2) . . ?
N1 C4 F3 116.6(2) . . ?
N1 C4 C5 124.17(18) . . ?
F4 C5 C1 120.90(18) . . ?
F4 C5 C4 120.38(17) . . ?
C4 C5 C1 118.71(19) . . ?
F5 C6 S1 109.54(12) . . ?
F5 C6 F6 104.47(15) . . ?
F5 C6 C7 111.70(14) . . ?
F6 C6 S1 109.14(11) . . ?
F6 C6 C7 111.40(15) . . ?
C7 C6 S1 110.41(12) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.37(15) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C9 C8 C7 120.42(17) . . ?
C13 C8 C7 120.57(16) . . ?
C13 C8 C9 119.01(17) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.11(19) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.66(18) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.45(19) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.21(19) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.55(17) . . ?
C12 C13 H13 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_854
_database_code_depnum_ccdc_archive 'CCDC 1947116'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
loop_
_audit_author_email
alex@xrlab.ineos.ac.ru
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 F4 N S, C19 H14 N'
_chemical_formula_sum            'C24 H14 F4 N2 S'
_chemical_formula_weight         438.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.6198(3)
_cell_length_b                   7.7249(3)
_cell_length_c                   29.3919(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.2010(10)
_cell_angle_gamma                90
_cell_volume                     1956.69(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7261
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.85
_cell_measurement_theta_min      2.364
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0599 before and 0.0455 after correction. The Ratio of minimum to maximum transmission is 0.8642. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            26990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.925
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4804
_reflns_number_total             6204
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.6686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1097
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C12A(H12A), C5A(H5A), C9A(H9A), C15A(H15A), C10A(H10A), C11A(H11A),
 C19A(H19A), C2A(H2A), C4A(H4A), C16A(H16A), C3A(H3A), C17A(H17A), C18A(H18A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F4 F 0.26572(9) 0.22688(12) 0.73441(3) 0.02933(19) Uani 1 1 d . . . . .
F1 F 0.56501(11) 0.34662(13) 0.60421(3) 0.0395(2) Uani 1 1 d . . . . .
F2 F 0.33722(13) 0.19699(13) 0.55407(3) 0.0415(2) Uani 1 1 d . . . . .
F3 F 0.05138(10) 0.09067(13) 0.67787(3) 0.0405(2) Uani 1 1 d . . . . .
N1A N 0.39293(13) 0.77427(14) 0.68908(4) 0.0230(2) Uani 1 1 d . . . . .
H1A H 0.4249 0.7923 0.7166 0.028 Uiso 1 1 calc R . . . .
N1 N 0.19327(15) 0.14519(16) 0.61591(4) 0.0296(3) Uani 1 1 d . . . . .
C8A C 0.19398(14) 0.67523(16) 0.63711(4) 0.0201(2) Uani 1 1 d . . . . .
C6A C 0.43513(14) 0.79566(16) 0.60884(4) 0.0211(2) Uani 1 1 d . . . . .
C7A C 0.28707(14) 0.72439(15) 0.60021(4) 0.0197(2) Uani 1 1 d . . . . .
C13A C 0.25164(15) 0.70064(16) 0.68239(4) 0.0213(2) Uani 1 1 d . . . . .
C14A C 0.22655(15) 0.70323(16) 0.55284(4) 0.0219(2) Uani 1 1 d . . . . .
C1A C 0.48636(14) 0.82094(17) 0.65478(5) 0.0230(2) Uani 1 1 d . . . . .
C5 C 0.29220(15) 0.22611(17) 0.68938(4) 0.0221(2) Uani 1 1 d . . . . .
C1 C 0.43028(14) 0.29649(16) 0.67294(4) 0.0213(2) Uani 1 1 d . . . . .
C12A C 0.16340(16) 0.64841(18) 0.72017(5) 0.0267(3) Uani 1 1 d . . . . .
H12A H 0.2014 0.6656 0.7497 0.032 Uiso 1 1 calc R . . . .
C5A C 0.53539(15) 0.85256(17) 0.57358(5) 0.0261(3) Uani 1 1 d . . . . .
H5A H 0.5046 0.8394 0.5433 0.031 Uiso 1 1 calc R . . . .
C2 C 0.43934(16) 0.28406(18) 0.62528(5) 0.0267(3) Uani 1 1 d . . . . .
C9A C 0.04470(15) 0.59738(18) 0.63140(5) 0.0256(3) Uani 1 1 d . . . . .
H9A H 0.0036 0.5806 0.6022 0.031 Uiso 1 1 calc R . . . .
C15A C 0.09615(16) 0.79686(18) 0.53848(5) 0.0271(3) Uani 1 1 d . . . . .
H15A H 0.0474 0.8710 0.5586 0.033 Uiso 1 1 calc R . . . .
C10A C -0.03863(16) 0.54716(19) 0.66804(5) 0.0292(3) Uani 1 1 d . . . . .
H10A H -0.1355 0.4961 0.6637 0.035 Uiso 1 1 calc R . . . .
C3 C 0.32258(19) 0.20912(18) 0.59960(4) 0.0294(3) Uani 1 1 d . . . . .
C11A C 0.02201(17) 0.57264(19) 0.71275(5) 0.0295(3) Uani 1 1 d . . . . .
H11A H -0.0356 0.5371 0.7375 0.035 Uiso 1 1 calc R . . . .
C19A C 0.29771(17) 0.59033(18) 0.52251(5) 0.0275(3) Uani 1 1 d . . . . .
H19A H 0.3842 0.5265 0.5319 0.033 Uiso 1 1 calc R . . . .
C4 C 0.18229(16) 0.15581(18) 0.66025(5) 0.0269(3) Uani 1 1 d . . . . .
C2A C 0.63293(16) 0.89714(19) 0.66486(5) 0.0301(3) Uani 1 1 d . . . . .
H2A H 0.6661 0.9126 0.6949 0.036 Uiso 1 1 calc R . . . .
C4A C 0.67571(16) 0.9259(2) 0.58407(6) 0.0321(3) Uani 1 1 d . . . . .
H4A H 0.7398 0.9621 0.5608 0.039 Uiso 1 1 calc R . . . .
C16A C 0.03880(19) 0.77967(19) 0.49416(5) 0.0338(3) Uani 1 1 d . . . . .
H16A H -0.0485 0.8417 0.4847 0.041 Uiso 1 1 calc R . . . .
C3A C 0.72439(17) 0.9473(2) 0.63000(6) 0.0362(3) Uani 1 1 d . . . . .
H3A H 0.8208 0.9965 0.6365 0.043 Uiso 1 1 calc R . . . .
C17A C 0.1119(2) 0.6700(2) 0.46407(5) 0.0376(4) Uani 1 1 d . . . . .
H17A H 0.0753 0.6612 0.4342 0.045 Uiso 1 1 calc R . . . .
C18A C 0.2388(2) 0.5737(2) 0.47831(5) 0.0357(3) Uani 1 1 d . . . . .
H18A H 0.2852 0.4974 0.4582 0.043 Uiso 1 1 calc R . . . .
S1 S 0.57080(4) 0.39116(5) 0.70657(2) 0.02727(9) 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
F4 C5 1.3477(14) . ?
F1 C2 1.3486(16) . ?
F2 C3 1.3501(16) . ?
F3 C4 1.3489(16) . ?
N1A H1A 0.8600 . ?
N1A C13A 1.3548(17) . ?
N1A C1A 1.3523(17) . ?
N1 C3 1.318(2) . ?
N1 C4 1.3112(19) . ?
C8A C7A 1.4147(17) . ?
C8A C13A 1.4244(18) . ?
C8A C9A 1.4271(18) . ?
C6A C7A 1.4081(17) . ?
C6A C1A 1.4253(18) . ?
C6A C5A 1.4324(18) . ?
C7A C14A 1.4854(17) . ?
C13A C12A 1.4175(18) . ?
C14A C15A 1.3946(19) . ?
C14A C19A 1.3981(18) . ?
C1A C2A 1.4194(19) . ?
C5 C1 1.4035(18) . ?
C5 C4 1.3753(18) . ?
C1 C2 1.4079(18) . ?
C1 S1 1.7114(13) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.365(2) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.365(2) . ?
C2 C3 1.373(2) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.3632(19) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.3898(19) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.418(2) . ?
C11A H11A 0.9300 . ?
C19A H19A 0.9300 . ?
C19A C18A 1.391(2) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.362(2) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.415(2) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.386(2) . ?
C3A H3A 0.9300 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.381(3) . ?
C18A H18A 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
C13A N1A H1A 118.3 . . ?
C1A N1A H1A 118.3 . . ?
C1A N1A C13A 123.46(11) . . ?
C4 N1 C3 114.65(12) . . ?
C7A C8A C13A 119.14(11) . . ?
C7A C8A C9A 123.19(12) . . ?
C13A C8A C9A 117.65(11) . . ?
C7A C6A C1A 119.08(11) . . ?
C7A C6A C5A 123.22(12) . . ?
C1A C6A C5A 117.63(12) . . ?
C8A C7A C14A 119.70(11) . . ?
C6A C7A C8A 119.56(11) . . ?
C6A C7A C14A 120.74(11) . . ?
N1A C13A C8A 119.24(11) . . ?
N1A C13A C12A 120.09(12) . . ?
C12A C13A C8A 120.67(12) . . ?
C15A C14A C7A 119.45(11) . . ?
C15A C14A C19A 119.48(13) . . ?
C19A C14A C7A 121.07(12) . . ?
N1A C1A C6A 119.48(12) . . ?
N1A C1A C2A 119.76(13) . . ?
C2A C1A C6A 120.75(12) . . ?
F4 C5 C1 119.91(11) . . ?
F4 C5 C4 118.98(12) . . ?
C4 C5 C1 121.11(12) . . ?
C5 C1 C2 112.41(12) . . ?
C5 C1 S1 124.18(10) . . ?
C2 C1 S1 123.40(10) . . ?
C13A C12A H12A 120.4 . . ?
C11A C12A C13A 119.27(13) . . ?
C11A C12A H12A 120.4 . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A C6A 120.61(14) . . ?
C4A C5A H5A 119.7 . . ?
F1 C2 C1 119.63(13) . . ?
F1 C2 C3 119.03(13) . . ?
C3 C2 C1 121.35(13) . . ?
C8A C9A H9A 119.5 . . ?
C10A C9A C8A 121.05(13) . . ?
C10A C9A H9A 119.5 . . ?
C14A C15A H15A 119.9 . . ?
C16A C15A C14A 120.19(14) . . ?
C16A C15A H15A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C9A C10A C11A 120.17(13) . . ?
C11A C10A H10A 119.9 . . ?
F2 C3 C2 119.43(14) . . ?
N1 C3 F2 115.57(13) . . ?
N1 C3 C2 125.00(13) . . ?
C12A C11A C10A 121.19(13) . . ?
C12A C11A H11A 119.4 . . ?
C10A C11A H11A 119.4 . . ?
C14A C19A H19A 120.1 . . ?
C18A C19A C14A 119.80(14) . . ?
C18A C19A H19A 120.1 . . ?
F3 C4 C5 118.62(12) . . ?
N1 C4 F3 115.90(12) . . ?
N1 C4 C5 125.48(13) . . ?
C1A C2A H2A 120.4 . . ?
C3A C2A C1A 119.18(14) . . ?
C3A C2A H2A 120.4 . . ?
C5A C4A H4A 119.8 . . ?
C5A C4A C3A 120.49(14) . . ?
C3A C4A H4A 119.8 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 119.93(15) . . ?
C17A C16A H16A 120.0 . . ?
C2A C3A C4A 121.33(13) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A C16A 120.27(14) . . ?
C18A C17A H17A 119.9 . . ?
C19A C18A H18A 119.8 . . ?
C17A C18A C19A 120.31(14) . . ?
C17A C18A H18A 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
