# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2027276'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 F4 N2 O S'
_chemical_formula_sum            'C12 H8 F4 N2 O S'
_chemical_formula_weight         304.26

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'
S S 0.1246 0.1234 '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'

_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                   5.7581(3)
_cell_length_b                   13.2226(6)
_cell_length_c                   16.3778(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.070(3)
_cell_angle_gamma                90
_cell_volume                     1245.17(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3277
_cell_measurement_theta_min      0.497
_cell_measurement_theta_max      30.508

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.306
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9840
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         26.249
_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             2501
_reflns_number_gt                1487
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0091P)²+1.5902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2501
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.63401(17) 0.13099(7) 0.42893(6) 0.0483(3) Uani 1 1 d . . . . .
F1 F 1.0826(4) 0.21748(17) 0.62422(13) 0.0657(7) Uani 1 1 d . . . . .
F2 F 1.0430(4) 0.38593(18) 0.71370(15) 0.0799(8) Uani 1 1 d . . . . .
F3 F 0.3677(5) 0.4707(2) 0.58074(16) 0.0876(8) Uani 1 1 d . . . . .
F4 F 0.3668(4) 0.30492(18) 0.48849(14) 0.0726(7) Uani 1 1 d . . . . .
O1 O 0.3942(4) 0.1011(2) 0.42133(17) 0.0666(8) Uani 1 1 d . . . . .
N1 N 0.7046(6) 0.4282(3) 0.6485(2) 0.0624(9) Uani 1 1 d . . . . .
N2 N 0.7522(5) 0.1593(2) 0.51238(17) 0.0509(8) Uani 1 1 d . . . . .
C1 C 0.8963(6) 0.2777(3) 0.6114(2) 0.0473(9) Uani 1 1 d . . . . .
C2 C 0.8768(7) 0.3638(3) 0.6557(2) 0.0569(10) Uani 1 1 d . . . . .
C3 C 0.5453(7) 0.4049(3) 0.5913(3) 0.0588(11) Uani 1 1 d . . . . .
C4 C 0.5447(6) 0.3204(3) 0.5437(2) 0.0511(10) Uani 1 1 d . . . . .
C5 C 0.7251(6) 0.2507(3) 0.5520(2) 0.0451(9) Uani 1 1 d . . . . .
C6 C 0.8052(7) 0.0292(3) 0.3995(2) 0.0599(11) Uani 1 1 d . . . . .
H6A H 0.789393 -0.026947 0.437912 0.090 Uiso 1 1 calc R U . . .
H6B H 0.968393 0.050292 0.399929 0.090 Uiso 1 1 calc R U . . .
H6C H 0.753558 0.007295 0.344364 0.090 Uiso 1 1 calc R U . . .
C7 C 0.6785(6) 0.2287(3) 0.3576(2) 0.0414(8) Uani 1 1 d . . . . .
C8 C 0.8848(6) 0.2836(3) 0.3631(2) 0.0469(9) Uani 1 1 d . . . . .
H8 H 1.004050 0.267301 0.403316 0.056 Uiso 1 1 calc R U . . .
C9 C 0.9128(7) 0.3620(3) 0.3093(2) 0.0553(10) Uani 1 1 d . . . . .
H9 H 1.052724 0.400205 0.312263 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7403(7) 0.3853(3) 0.2514(2) 0.0575(10) Uani 1 1 d . . . . .
H10 H 0.760372 0.440047 0.214838 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5398(7) 0.3301(3) 0.2461(2) 0.0613(11) Uani 1 1 d . . . . .
H11 H 0.422028 0.346419 0.205368 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5058(6) 0.2508(3) 0.2990(2) 0.0513(10) Uani 1 1 d . . . . .
H12 H 0.366260 0.212343 0.295090 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 1.436(3) . ?
S1 N2 1.540(3) . ?
S1 C6 1.751(4) . ?
S1 C7 1.770(4) . ?
F1 C1 1.343(4) . ?
F2 C2 1.343(4) . ?
F3 C3 1.347(4) . ?
F4 C4 1.345(4) . ?
N1 C2 1.308(5) . ?
N1 C3 1.311(5) . ?
N2 C5 1.385(4) . ?
C1 C2 1.358(5) . ?
C1 C5 1.394(5) . ?
C3 C4 1.362(5) . ?
C4 C5 1.389(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.375(4) . ?
C7 C8 1.391(5) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 H12 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 N2 121.41(18) . . ?
O1 S1 C6 108.50(18) . . ?
N2 S1 C6 101.65(17) . . ?
O1 S1 C7 108.45(16) . . ?
N2 S1 C7 109.63(16) . . ?
C6 S1 C7 106.05(18) . . ?
C2 N1 C3 114.2(4) . . ?
C5 N2 S1 124.9(3) . . ?
F1 C1 C2 120.1(3) . . ?
F1 C1 C5 119.1(3) . . ?
C2 C1 C5 120.8(4) . . ?
N1 C2 F2 115.5(4) . . ?
N1 C2 C1 125.5(4) . . ?
F2 C2 C1 118.9(4) . . ?
N1 C3 F3 115.9(4) . . ?
N1 C3 C4 125.6(4) . . ?
F3 C3 C4 118.5(4) . . ?
F4 C4 C3 119.2(4) . . ?
F4 C4 C5 120.2(3) . . ?
C3 C4 C5 120.6(3) . . ?
N2 C5 C4 129.4(3) . . ?
N2 C5 C1 117.2(3) . . ?
C4 C5 C1 113.3(3) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 121.2(3) . . ?
C12 C7 S1 119.4(3) . . ?
C8 C7 S1 119.4(3) . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 118.5(4) . . ?
C7 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_(R)-3a
_database_code_depnum_ccdc_archive 'CCDC 2027277'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        (R)-3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 F4 N2 O S'
_chemical_formula_sum            'C12 H8 F4 N2 O S'
_chemical_formula_weight         304.26

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'
S S 0.1246 0.1234 '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'

_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                   5.5411(2)
_cell_length_b                   25.4002(14)
_cell_length_c                   8.8415(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.752(3)
_cell_angle_gamma                90
_cell_volume                     1243.82(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2643
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.306
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6243
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6671
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             3949
_reflns_number_gt                3120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.747
_reflns_Friedel_fraction_full    0.747

_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0066P)²+2.8239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3949
_refine_ls_number_parameters     363
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.020
_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
S1 S 0.7114(3) 0.61305(9) 0.4558(2) 0.0266(5) Uani 1 1 d . . . . .
F1 F 0.2930(10) 0.6562(2) 0.8004(6) 0.0500(16) Uani 1 1 d . . . . .
F2 F 0.2678(10) 0.6059(3) 1.0681(6) 0.0566(17) Uani 1 1 d . . . . .
F3 F 0.9497(10) 0.5145(3) 0.9856(7) 0.0554(17) Uani 1 1 d . . . . .
F4 F 1.0060(9) 0.5586(2) 0.7164(6) 0.0488(15) Uani 1 1 d . . . . .
O1 O 0.9492(10) 0.5959(3) 0.4154(7) 0.0410(18) Uani 1 1 d . . . . .
N1 N 0.6629(13) 0.6383(3) 0.6099(8) 0.0334(17) Uani 1 1 d . . . . .
N2 N 0.6081(15) 0.5606(3) 1.0268(9) 0.040(2) Uani 1 1 d . . . . .
C1 C 0.6482(14) 0.6098(4) 0.7423(9) 0.0257(15) Uani 1 1 d . . . . .
C2 C 0.4606(16) 0.6204(4) 0.8417(10) 0.035(2) Uani 1 1 d . . . . .
C3 C 0.4510(17) 0.5954(4) 0.9755(11) 0.037(2) Uani 1 1 d . . . . .
C4 C 0.7868(17) 0.5493(4) 0.9369(11) 0.035(2) Uani 1 1 d . . . . .
C5 C 0.8150(16) 0.5730(4) 0.7970(10) 0.032(2) Uani 1 1 d . . . . .
C6 C 0.6243(14) 0.6646(4) 0.3298(10) 0.028(2) Uani 1 1 d . . . . .
C7 C 0.7768(16) 0.6749(4) 0.2128(11) 0.036(2) Uani 1 1 d . . . . .
H7 H 0.917536 0.654201 0.199665 0.043 Uiso 1 1 calc R U . . .
C8 C 0.720(2) 0.7161(5) 0.1148(13) 0.052(3) Uani 1 1 d . . . . .
H8 H 0.821566 0.723832 0.033184 0.063 Uiso 1 1 calc R U . . .
C9 C 0.517(2) 0.7455(5) 0.1358(14) 0.054(3) Uani 1 1 d . . . . .
H9 H 0.480400 0.774332 0.070651 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3610(17) 0.7330(4) 0.2542(12) 0.041(3) Uani 1 1 d . . . . .
H10 H 0.217188 0.752770 0.265745 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4149(15) 0.6928(4) 0.3525(11) 0.035(2) Uani 1 1 d . . . . .
H11 H 0.312307 0.684552 0.433336 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5087(14) 0.5600(3) 0.4220(10) 0.028(2) Uani 1 1 d . . . . .
H12A H 0.524531 0.547359 0.318063 0.042 Uiso 1 1 calc R U . . .
H12B H 0.342851 0.572063 0.436125 0.042 Uiso 1 1 calc R U . . .
H12C H 0.546661 0.531390 0.493029 0.042 Uiso 1 1 calc R U . . .
S2 S -0.0636(4) 0.42806(9) 0.4463(3) 0.0289(5) Uani 1 1 d . . . . .
F5 F 0.4811(9) 0.4742(2) 0.7603(6) 0.0471(15) Uani 1 1 d . . . . .
F6 F 0.5669(10) 0.4279(3) 1.0308(7) 0.0580(16) Uani 1 1 d . . . . .
F7 F -0.0945(12) 0.3255(3) 0.9779(7) 0.0648(19) Uani 1 1 d . . . . .
F8 F -0.2173(9) 0.3667(2) 0.7095(6) 0.0466(15) Uani 1 1 d . . . . .
O2 O -0.3202(10) 0.4378(3) 0.4469(7) 0.0380(16) Uani 1 1 d . . . . .
N3 N 0.1060(13) 0.4454(3) 0.5791(9) 0.0358(19) Uani 1 1 d . . . . .
N4 N 0.2364(15) 0.3761(3) 1.0046(9) 0.043(2) Uani 1 1 d . . . . .
C13 C 0.1292(15) 0.4221(4) 0.7186(9) 0.029(2) Uani 1 1 d . . . . .
C14 C 0.3288(15) 0.4363(4) 0.8095(10) 0.034(2) Uani 1 1 d . . . . .
C15 C 0.3722(17) 0.4136(4) 0.9473(11) 0.040(3) Uani 1 1 d . . . . .
C16 C 0.0478(18) 0.3633(4) 0.9215(13) 0.042(3) Uani 1 1 d . . . . .
C17 C -0.0140(16) 0.3832(4) 0.7827(11) 0.034(2) Uani 1 1 d . . . . .
C18 C -0.0180(14) 0.3607(3) 0.4047(10) 0.028(2) Uani 1 1 d . . . . .
C19 C -0.2055(15) 0.3341(4) 0.3280(10) 0.031(2) Uani 1 1 d . . . . .
H19 H -0.349057 0.352015 0.296931 0.038 Uiso 1 1 calc R U . . .
C20 C -0.1776(17) 0.2812(4) 0.2985(11) 0.038(2) Uani 1 1 d . . . . .
H20 H -0.301806 0.262727 0.244449 0.046 Uiso 1 1 calc R U . . .
C21 C 0.0265(18) 0.2550(4) 0.3458(11) 0.038(2) Uani 1 1 d . . . . .
H21 H 0.041657 0.218349 0.327215 0.046 Uiso 1 1 calc R U . . .
C22 C 0.2138(17) 0.2824(4) 0.4220(12) 0.044(3) Uani 1 1 d . . . . .
H22 H 0.356734 0.264398 0.454089 0.053 Uiso 1 1 calc R U . . .
C23 C 0.1891(15) 0.3356(4) 0.4502(11) 0.034(2) Uani 1 1 d . . . . .
H23 H 0.315460 0.354540 0.500789 0.041 Uiso 1 1 calc R U . . .
C24 C 0.0629(17) 0.4624(4) 0.2953(11) 0.036(2) Uani 1 1 d . . . . .
H24A H -0.019538 0.452097 0.200232 0.054 Uiso 1 1 calc R U . . .
H24B H 0.234965 0.453822 0.290669 0.054 Uiso 1 1 calc R U . . .
H24C H 0.043783 0.500322 0.310967 0.054 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 1.444(6) . ?
S1 N1 1.537(8) . ?
S1 C12 1.773(8) . ?
S1 C6 1.777(9) . ?
F1 C2 1.341(10) . ?
F2 C3 1.350(11) . ?
F3 C4 1.327(10) . ?
F4 C5 1.345(10) . ?
N1 C1 1.381(11) . ?
N2 C3 1.312(12) . ?
N2 C4 1.320(12) . ?
C1 C5 1.391(12) . ?
C1 C2 1.407(12) . ?
C2 C3 1.346(13) . ?
C4 C5 1.388(13) . ?
C6 C7 1.380(12) . ?
C6 C11 1.383(12) . ?
C7 C8 1.390(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.368(13) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S2 O2 1.443(6) . ?
S2 N3 1.545(8) . ?
S2 C24 1.758(9) . ?
S2 C18 1.769(9) . ?
F5 C14 1.360(11) . ?
F6 C15 1.338(10) . ?
F7 C16 1.348(11) . ?
F8 C17 1.348(10) . ?
N3 C13 1.371(11) . ?
N4 C16 1.300(13) . ?
N4 C15 1.325(13) . ?
C13 C14 1.394(11) . ?
C13 C17 1.399(13) . ?
C14 C15 1.362(13) . ?
C16 C17 1.361(14) . ?
C18 C23 1.363(12) . ?
C18 C19 1.398(12) . ?
C19 C20 1.377(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.367(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.404(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(14) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 N1 122.1(4) . . ?
O1 S1 C12 107.9(4) . . ?
N1 S1 C12 109.9(4) . . ?
O1 S1 C6 107.5(4) . . ?
N1 S1 C6 101.3(4) . . ?
C12 S1 C6 107.2(4) . . ?
C1 N1 S1 123.3(7) . . ?
C3 N2 C4 116.1(9) . . ?
N1 C1 C5 126.2(8) . . ?
N1 C1 C2 119.5(8) . . ?
C5 C1 C2 114.0(8) . . ?
F1 C2 C3 120.9(8) . . ?
F1 C2 C1 118.6(8) . . ?
C3 C2 C1 120.5(9) . . ?
N2 C3 C2 125.4(9) . . ?
N2 C3 F2 115.3(9) . . ?
C2 C3 F2 119.3(9) . . ?
N2 C4 F3 117.7(9) . . ?
N2 C4 C5 123.3(9) . . ?
F3 C4 C5 119.0(9) . . ?
F4 C5 C4 117.7(8) . . ?
F4 C5 C1 121.6(8) . . ?
C4 C5 C1 120.6(9) . . ?
C7 C6 C11 123.2(9) . . ?
C7 C6 S1 116.6(7) . . ?
C11 C6 S1 120.2(7) . . ?
C6 C7 C8 118.4(10) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 119.9(11) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.1(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.8(9) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 117.5(9) . . ?
C10 C11 H11 121.2 . . ?
C6 C11 H11 121.2 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S2 N3 121.6(4) . . ?
O2 S2 C24 109.5(4) . . ?
N3 S2 C24 100.8(4) . . ?
O2 S2 C18 108.3(4) . . ?
N3 S2 C18 110.3(4) . . ?
C24 S2 C18 105.0(4) . . ?
C13 N3 S2 126.8(6) . . ?
C16 N4 C15 114.8(9) . . ?
N3 C13 C14 117.3(8) . . ?
N3 C13 C17 129.1(8) . . ?
C14 C13 C17 113.5(8) . . ?
F5 C14 C15 119.4(8) . . ?
F5 C14 C13 119.2(8) . . ?
C15 C14 C13 121.4(9) . . ?
N4 C15 F6 116.2(9) . . ?
N4 C15 C14 124.0(9) . . ?
F6 C15 C14 119.8(9) . . ?
N4 C16 F7 116.0(10) . . ?
N4 C16 C17 126.3(9) . . ?
F7 C16 C17 117.6(9) . . ?
F8 C17 C16 120.1(9) . . ?
F8 C17 C13 120.1(9) . . ?
C16 C17 C13 119.8(8) . . ?
C23 C18 C19 121.5(9) . . ?
C23 C18 S2 121.0(7) . . ?
C19 C18 S2 117.4(6) . . ?
C20 C19 C18 118.5(8) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C19 120.9(9) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.9(9) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.7(9) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C18 C23 C22 119.5(9) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 2027280'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3e
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Cl F4 N2 O S'
_chemical_formula_sum            'C12 H7 Cl F4 N2 O S'
_chemical_formula_weight         338.71

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'
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'
F F 0.0171 0.0103 '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                   5.47560(10)
_cell_length_b                   12.9051(5)
_cell_length_c                   18.9309(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.519(2)
_cell_angle_gamma                90
_cell_volume                     1335.20(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.488
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6381
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8050
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_max         28.849
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3451
_reflns_number_gt                2728
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0324P)²+0.8132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
S1 S 0.64153(8) 0.13108(4) 0.44126(2) 0.02142(12) Uani 1 1 d . . . . .
Cl1 Cl 0.73131(10) 0.44129(4) 0.19130(3) 0.03658(15) Uani 1 1 d . . . . .
F1 F 1.1051(2) 0.21841(10) 0.61651(7) 0.0401(3) Uani 1 1 d . . . . .
F2 F 1.0359(3) 0.38124(12) 0.70073(9) 0.0635(5) Uani 1 1 d . . . . .
F3 F 0.3497(3) 0.47700(12) 0.57314(9) 0.0560(4) Uani 1 1 d . . . . .
F4 F 0.3767(2) 0.31667(11) 0.48554(7) 0.0424(3) Uani 1 1 d . . . . .
O1 O 0.3859(2) 0.10257(11) 0.44181(7) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.7871(3) 0.16807(13) 0.50907(8) 0.0253(3) Uani 1 1 d . . . . .
N2 N 0.6934(4) 0.42960(16) 0.63772(11) 0.0446(5) Uani 1 1 d . . . . .
C1 C 0.7406(3) 0.25626(15) 0.54696(10) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.9087(4) 0.27950(16) 0.60372(11) 0.0300(4) Uani 1 1 d . . . . .
C3 C 0.8743(5) 0.36316(19) 0.64598(12) 0.0408(6) Uani 1 1 d . . . . .
C4 C 0.5366(4) 0.40986(18) 0.58381(13) 0.0375(5) Uani 1 1 d . . . . .
C5 C 0.5505(4) 0.32753(17) 0.53830(11) 0.0303(4) Uani 1 1 d . . . . .
C6 C 0.6709(3) 0.22035(15) 0.37108(10) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.4887(4) 0.22226(17) 0.31666(10) 0.0283(4) Uani 1 1 d . . . . .
H7 H 0.351814 0.177188 0.317609 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5094(4) 0.29057(18) 0.26116(11) 0.0313(5) Uani 1 1 d . . . . .
H8 H 0.387397 0.292744 0.223281 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7097(4) 0.35567(15) 0.26142(10) 0.0256(4) Uani 1 1 d . . . . .
C10 C 0.8926(4) 0.35402(16) 0.31507(11) 0.0279(4) Uani 1 1 d . . . . .
H10 H 1.029410 0.399121 0.313848 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8726(3) 0.28519(16) 0.37078(10) 0.0265(4) Uani 1 1 d . . . . .
H11 H 0.995895 0.282565 0.408299 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8128(3) 0.02304(15) 0.41762(10) 0.0264(4) Uani 1 1 d . . . . .
H12A H 0.796565 -0.032138 0.452586 0.040 Uiso 1 1 calc R U . . .
H12B H 0.985333 0.042638 0.416214 0.040 Uiso 1 1 calc R U . . .
H12C H 0.752162 -0.001745 0.370850 0.040 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 1.4479(14) . ?
S1 N1 1.5445(16) . ?
S1 C12 1.754(2) . ?
S1 C6 1.7733(19) . ?
Cl1 C9 1.737(2) . ?
F1 C2 1.343(2) . ?
F2 C3 1.341(3) . ?
F3 C4 1.346(3) . ?
F4 C5 1.344(2) . ?
N1 C1 1.377(2) . ?
N2 C3 1.312(3) . ?
N2 C4 1.318(3) . ?
C1 C5 1.391(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.364(3) . ?
C4 C5 1.373(3) . ?
C6 C11 1.386(3) . ?
C6 C7 1.389(2) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 121.48(9) . . ?
O1 S1 C12 109.40(9) . . ?
N1 S1 C12 101.60(9) . . ?
O1 S1 C6 107.61(8) . . ?
N1 S1 C6 110.86(9) . . ?
C12 S1 C6 104.53(9) . . ?
C1 N1 S1 125.87(14) . . ?
C3 N2 C4 114.7(2) . . ?
N1 C1 C5 130.22(18) . . ?
N1 C1 C2 116.22(17) . . ?
C5 C1 C2 113.56(19) . . ?
F1 C2 C3 119.79(19) . . ?
F1 C2 C1 119.52(18) . . ?
C3 C2 C1 120.7(2) . . ?
N2 C3 F2 115.8(2) . . ?
N2 C3 C2 125.3(2) . . ?
F2 C3 C2 118.9(2) . . ?
N2 C4 F3 116.4(2) . . ?
N2 C4 C5 125.2(2) . . ?
F3 C4 C5 118.3(2) . . ?
F4 C5 C4 118.88(19) . . ?
F4 C5 C1 120.61(19) . . ?
C4 C5 C1 120.5(2) . . ?
C11 C6 C7 121.48(18) . . ?
C11 C6 S1 120.28(14) . . ?
C7 C6 S1 118.24(15) . . ?
C8 C7 C6 119.12(18) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 119.17(18) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 122.18(18) . . ?
C8 C9 Cl1 118.40(15) . . ?
C10 C9 Cl1 119.42(15) . . ?
C9 C10 C11 118.73(18) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C6 C11 C10 119.30(18) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 2027281'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3f
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Br F4 N2 O S'
_chemical_formula_sum            'C12 H7 Br F4 N2 O S'
_chemical_formula_weight         383.17

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'
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'
F F 0.0171 0.0103 '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                   16.8483(8)
_cell_length_b                   12.6532(5)
_cell_length_c                   13.1573(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.596(2)
_cell_angle_gamma                90
_cell_volume                     2642.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4464
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.316
_shelx_estimated_absorpt_T_min   0.366
_shelx_estimated_absorpt_T_max   0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5842
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13631
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.058
_diffrn_reflns_theta_max         28.865
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6790
_reflns_number_gt                3779
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0403P)²+2.8193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6790
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Br1 Br 0.57164(4) 0.53994(4) 0.64387(4) 0.04448(17) Uani 1 1 d . . . . .
S1 S 0.48718(8) 0.70727(9) 0.78639(10) 0.0320(3) Uani 1 1 d . . . . .
F1 F 0.32686(18) 0.5087(2) 0.5504(2) 0.0450(7) Uani 1 1 d . . . . .
F2 F 0.23864(19) 0.5671(3) 0.3480(2) 0.0602(9) Uani 1 1 d . . . . .
F3 F 0.3284(2) 0.9037(3) 0.4118(3) 0.0712(11) Uani 1 1 d . . . . .
F4 F 0.4160(2) 0.8629(2) 0.6158(3) 0.0592(9) Uani 1 1 d . . . . .
O1 O 0.4674(2) 0.7964(3) 0.8424(3) 0.0439(9) Uani 1 1 d . . . . .
N1 N 0.4168(2) 0.6475(3) 0.6992(3) 0.0314(9) Uani 1 1 d . . . . .
N2 N 0.2836(3) 0.7342(4) 0.3792(4) 0.0512(13) Uani 1 1 d . . . . .
C1 C 0.3770(3) 0.6829(4) 0.5959(4) 0.0316(11) Uani 1 1 d . . . . .
C2 C 0.3295(3) 0.6089(4) 0.5203(4) 0.0344(11) Uani 1 1 d . . . . .
C3 C 0.2852(3) 0.6392(5) 0.4169(4) 0.0431(13) Uani 1 1 d . . . . .
C5 C 0.3749(3) 0.7838(4) 0.5539(4) 0.0387(12) Uani 1 1 d . . . . .
C4 C 0.3284(4) 0.8044(5) 0.4472(5) 0.0488(15) Uani 1 1 d . . . . .
C6 C 0.5693(3) 0.7470(4) 0.7375(4) 0.0300(10) Uani 1 1 d . . . . .
C7 C 0.6050(3) 0.6825(3) 0.6779(4) 0.0307(11) Uani 1 1 d . . . . .
C8 C 0.6678(3) 0.7215(4) 0.6428(4) 0.0385(12) Uani 1 1 d . . . . .
H8 H 0.691444 0.677517 0.601853 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6969(3) 0.8238(4) 0.6667(4) 0.0425(13) Uani 1 1 d . . . . .
H9 H 0.740948 0.849514 0.643495 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6611(3) 0.8891(4) 0.7249(4) 0.0377(12) Uani 1 1 d . . . . .
H10 H 0.679832 0.960021 0.740020 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5984(3) 0.8504(3) 0.7605(4) 0.0335(11) Uani 1 1 d . . . . .
H11 H 0.574814 0.894709 0.801216 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5310(3) 0.6078(4) 0.8819(4) 0.0392(12) Uani 1 1 d . . . . .
H12A H 0.572641 0.639076 0.945898 0.059 Uiso 1 1 calc R U . . .
H12B H 0.558586 0.554937 0.850647 0.059 Uiso 1 1 calc R U . . .
H12C H 0.486376 0.573938 0.902530 0.059 Uiso 1 1 calc R U . . .
Br2 Br 0.09980(4) 0.29745(4) 0.37229(4) 0.04302(16) Uani 1 1 d . . . . .
S2 S -0.04103(8) 0.46663(9) 0.19603(9) 0.0311(3) Uani 1 1 d . . . . .
F5 F 0.12653(19) 0.2654(2) 0.1218(2) 0.0445(7) Uani 1 1 d . . . . .
F6 F 0.26571(19) 0.3259(3) 0.0795(2) 0.0563(9) Uani 1 1 d . . . . .
F7 F 0.2045(2) 0.6711(3) 0.0930(3) 0.0625(9) Uani 1 1 d . . . . .
F8 F 0.06140(18) 0.6286(2) 0.1302(2) 0.0455(7) Uani 1 1 d . . . . .
O2 O -0.0934(2) 0.5560(3) 0.1493(3) 0.0400(8) Uani 1 1 d . . . . .
N3 N 0.0112(2) 0.4081(3) 0.1380(3) 0.0302(9) Uani 1 1 d . . . . .
N4 N 0.2360(3) 0.4968(4) 0.0877(3) 0.0449(11) Uani 1 1 d . . . . .
C13 C 0.0855(3) 0.4446(4) 0.1267(3) 0.0305(11) Uani 1 1 d . . . . .
C14 C 0.1426(3) 0.3677(4) 0.1144(3) 0.0344(11) Uani 1 1 d . . . . .
C15 C 0.2140(3) 0.3998(5) 0.0946(4) 0.0399(13) Uani 1 1 d . . . . .
C16 C 0.1837(4) 0.5698(5) 0.1008(4) 0.0425(13) Uani 1 1 d . . . . .
C17 C 0.1100(3) 0.5482(4) 0.1198(3) 0.0339(11) Uani 1 1 d . . . . .
C18 C 0.0242(3) 0.5059(4) 0.3288(3) 0.0296(10) Uani 1 1 d . . . . .
C19 C 0.0838(3) 0.4413(4) 0.4006(4) 0.0321(11) Uani 1 1 d . . . . .
C20 C 0.1342(3) 0.4811(4) 0.4987(4) 0.0372(12) Uani 1 1 d . . . . .
H20 H 0.174688 0.437048 0.548172 0.045 Uiso 1 1 calc R U . . .
C21 C 0.1254(3) 0.5846(4) 0.5244(4) 0.0402(13) Uani 1 1 d . . . . .
H21 H 0.161577 0.612734 0.590714 0.048 Uiso 1 1 calc R U . . .
C22 C 0.0652(3) 0.6478(4) 0.4555(4) 0.0407(13) Uani 1 1 d . . . . .
H22 H 0.058445 0.718515 0.475433 0.049 Uiso 1 1 calc R U . . .
C23 C 0.0145(3) 0.6095(4) 0.3577(4) 0.0372(12) Uani 1 1 d . . . . .
H23 H -0.027038 0.653605 0.309928 0.045 Uiso 1 1 calc R U . . .
C24 C -0.1081(3) 0.3663(4) 0.2114(4) 0.0410(12) Uani 1 1 d . . . . .
H24A H -0.149143 0.396450 0.241272 0.062 Uiso 1 1 calc R U . . .
H24B H -0.074714 0.312149 0.260599 0.062 Uiso 1 1 calc R U . . .
H24C H -0.137770 0.334409 0.141056 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
Br1 C7 1.897(4) . ?
S1 O1 1.445(3) . ?
S1 N1 1.543(4) . ?
S1 C12 1.757(5) . ?
S1 C6 1.783(5) . ?
F1 C2 1.334(5) . ?
F2 C3 1.339(6) . ?
F3 C4 1.340(6) . ?
F4 C5 1.329(6) . ?
N1 C1 1.374(6) . ?
N2 C3 1.297(7) . ?
N2 C4 1.307(7) . ?
C1 C5 1.387(7) . ?
C1 C2 1.404(7) . ?
C2 C3 1.368(7) . ?
C5 C4 1.383(8) . ?
C6 C11 1.394(6) . ?
C6 C7 1.400(6) . ?
C7 C8 1.380(7) . ?
C8 C9 1.383(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Br2 C19 1.896(5) . ?
S2 O2 1.439(3) . ?
S2 N3 1.535(4) . ?
S2 C24 1.755(5) . ?
S2 C18 1.795(5) . ?
F5 C14 1.333(5) . ?
F6 C15 1.337(6) . ?
F7 C16 1.342(6) . ?
F8 C17 1.341(5) . ?
N3 C13 1.389(6) . ?
N4 C15 1.295(7) . ?
N4 C16 1.327(7) . ?
C13 C17 1.387(6) . ?
C13 C14 1.415(7) . ?
C14 C15 1.375(7) . ?
C16 C17 1.373(7) . ?
C18 C23 1.389(7) . ?
C18 C19 1.389(6) . ?
C19 C20 1.380(6) . ?
C20 C21 1.373(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 N1 120.7(2) . . ?
O1 S1 C12 107.9(2) . . ?
N1 S1 C12 102.4(2) . . ?
O1 S1 C6 107.7(2) . . ?
N1 S1 C6 111.4(2) . . ?
C12 S1 C6 105.6(2) . . ?
C1 N1 S1 125.1(3) . . ?
C3 N2 C4 115.7(5) . . ?
N1 C1 C5 129.3(5) . . ?
N1 C1 C2 117.2(4) . . ?
C5 C1 C2 113.5(4) . . ?
F1 C2 C3 120.0(5) . . ?
F1 C2 C1 119.4(4) . . ?
C3 C2 C1 120.6(5) . . ?
N2 C3 F2 116.1(5) . . ?
N2 C3 C2 125.1(5) . . ?
F2 C3 C2 118.9(5) . . ?
F4 C5 C4 118.8(5) . . ?
F4 C5 C1 120.7(5) . . ?
C4 C5 C1 120.5(5) . . ?
N2 C4 F3 117.8(5) . . ?
N2 C4 C5 124.6(5) . . ?
F3 C4 C5 117.6(6) . . ?
C11 C6 C7 118.9(4) . . ?
C11 C6 S1 116.4(4) . . ?
C7 C6 S1 124.7(3) . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 Br1 117.5(3) . . ?
C6 C7 Br1 122.5(3) . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S2 N3 122.6(2) . . ?
O2 S2 C24 107.0(2) . . ?
N3 S2 C24 101.9(2) . . ?
O2 S2 C18 106.6(2) . . ?
N3 S2 C18 110.6(2) . . ?
C24 S2 C18 107.2(2) . . ?
C13 N3 S2 125.5(3) . . ?
C15 N4 C16 115.6(5) . . ?
C17 C13 N3 128.4(4) . . ?
C17 C13 C14 114.4(4) . . ?
N3 C13 C14 117.1(4) . . ?
F5 C14 C15 120.8(5) . . ?
F5 C14 C13 119.8(4) . . ?
C15 C14 C13 119.4(5) . . ?
N4 C15 F6 115.9(5) . . ?
N4 C15 C14 125.6(5) . . ?
F6 C15 C14 118.5(5) . . ?
N4 C16 F7 116.9(5) . . ?
N4 C16 C17 124.5(5) . . ?
F7 C16 C17 118.6(5) . . ?
F8 C17 C16 119.2(5) . . ?
F8 C17 C13 120.3(4) . . ?
C16 C17 C13 120.5(5) . . ?
C23 C18 C19 119.6(4) . . ?
C23 C18 S2 116.0(4) . . ?
C19 C18 S2 124.4(4) . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 Br2 116.8(4) . . ?
C18 C19 Br2 123.3(4) . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.3(5) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 119.8(5) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.897
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.107



####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 2027282'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3g
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Br F4 N2 O S'
_chemical_formula_sum            'C12 H7 Br F4 N2 O S'
_chemical_formula_weight         383.17

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'
S S 0.1246 0.1234 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9637(4)
_cell_length_b                   8.0951(3)
_cell_length_c                   11.7482(5)
_cell_angle_alpha                71.8680(10)
_cell_angle_beta                 75.506(2)
_cell_angle_gamma                71.1250(10)
_cell_volume                     671.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1714
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.262
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6354
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.741
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3442
_reflns_number_gt                2382
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0264P)²+0.5946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.68546(6) -0.36297(5) 0.46423(4) 0.04938(16) Uani 1 1 d . . . . .
S1 S 0.80116(11) 0.24101(10) 0.10680(7) 0.02552(19) Uani 1 1 d . . . . .
F1 F 0.6310(3) 0.7760(3) 0.12816(19) 0.0391(5) Uani 1 1 d . . . . .
F2 F 0.3015(3) 0.9385(3) 0.22988(19) 0.0456(6) Uani 1 1 d . . . . .
F3 F 0.0878(3) 0.4710(3) 0.2627(2) 0.0560(7) Uani 1 1 d . . . . .
F4 F 0.4076(3) 0.2804(3) 0.1730(2) 0.0424(5) Uani 1 1 d . . . . .
O1 O 0.7532(3) 0.1428(3) 0.0422(2) 0.0323(6) Uani 1 1 d . . . . .
N1 N 0.7133(4) 0.4445(3) 0.0955(2) 0.0260(6) Uani 1 1 d . . . . .
N2 N 0.1945(4) 0.7043(4) 0.2485(3) 0.0372(7) Uani 1 1 d . . . . .
C1 C 0.5389(4) 0.5169(4) 0.1478(3) 0.0260(7) Uani 1 1 d . . . . .
C2 C 0.5007(5) 0.6906(4) 0.1639(3) 0.0276(7) Uani 1 1 d . . . . .
C3 C 0.3320(5) 0.7730(4) 0.2135(3) 0.0299(8) Uani 1 1 d . . . . .
C4 C 0.2275(5) 0.5442(5) 0.2315(3) 0.0355(9) Uani 1 1 d . . . . .
C5 C 0.3911(5) 0.4457(4) 0.1843(3) 0.0305(8) Uani 1 1 d . . . . .
C6 C 0.7835(4) 0.1230(4) 0.2629(3) 0.0246(7) Uani 1 1 d . . . . .
C7 C 0.7490(4) -0.0443(4) 0.2957(3) 0.0277(7) Uani 1 1 d . . . . .
H7 H 0.736287 -0.095417 0.236683 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7337(5) -0.1339(4) 0.4175(3) 0.0313(8) Uani 1 1 d . . . . .
C9 C 0.7513(5) -0.0617(5) 0.5040(3) 0.0378(9) Uani 1 1 d . . . . .
H9 H 0.739166 -0.125481 0.587249 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7872(5) 0.1063(5) 0.4682(3) 0.0403(9) Uani 1 1 d . . . . .
H10 H 0.801157 0.156340 0.527311 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8026(5) 0.2005(5) 0.3477(3) 0.0322(8) Uani 1 1 d . . . . .
H11 H 0.825800 0.315565 0.323130 0.039 Uiso 1 1 calc R U . . .
C12 C 1.0301(5) 0.2350(5) 0.0564(3) 0.0350(9) Uani 1 1 d . . . . .
H12A H 1.100277 0.111537 0.053902 0.053 Uiso 1 1 calc R U . . .
H12B H 1.072482 0.274616 0.112299 0.053 Uiso 1 1 calc R U . . .
H12C H 1.045088 0.315455 -0.025130 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
Br1 C8 1.900(3) . ?
S1 O1 1.439(2) . ?
S1 N1 1.545(3) . ?
S1 C12 1.760(3) . ?
S1 C6 1.779(3) . ?
F1 C2 1.340(4) . ?
F2 C3 1.348(4) . ?
F3 C4 1.345(4) . ?
F4 C5 1.347(4) . ?
N1 C1 1.385(4) . ?
N2 C4 1.305(5) . ?
N2 C3 1.305(5) . ?
C1 C5 1.391(5) . ?
C1 C2 1.402(4) . ?
C2 C3 1.364(5) . ?
C4 C5 1.372(5) . ?
C6 C7 1.386(4) . ?
C6 C11 1.390(5) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(5) . ?
C9 C10 1.394(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 121.93(16) . . ?
O1 S1 C12 108.49(16) . . ?
N1 S1 C12 101.75(15) . . ?
O1 S1 C6 108.24(14) . . ?
N1 S1 C6 109.43(15) . . ?
C12 S1 C6 105.79(17) . . ?
C1 N1 S1 124.5(2) . . ?
C4 N2 C3 114.8(3) . . ?
N1 C1 C5 129.8(3) . . ?
N1 C1 C2 116.4(3) . . ?
C5 C1 C2 113.7(3) . . ?
F1 C2 C3 120.3(3) . . ?
F1 C2 C1 119.3(3) . . ?
C3 C2 C1 120.4(3) . . ?
N2 C3 F2 116.0(3) . . ?
N2 C3 C2 125.4(3) . . ?
F2 C3 C2 118.6(3) . . ?
N2 C4 F3 116.7(3) . . ?
N2 C4 C5 125.6(3) . . ?
F3 C4 C5 117.7(3) . . ?
F4 C5 C4 119.7(3) . . ?
F4 C5 C1 120.2(3) . . ?
C4 C5 C1 120.1(3) . . ?
C7 C6 C11 122.3(3) . . ?
C7 C6 S1 118.0(2) . . ?
C11 C6 S1 119.7(2) . . ?
C8 C7 C6 117.5(3) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C9 C8 C7 122.0(3) . . ?
C9 C8 Br1 119.9(2) . . ?
C7 C8 Br1 118.1(3) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 118.4(3) . . ?
C10 C11 H11 120.8 . . ?
C6 C11 H11 120.8 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.093



####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 2027283'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3h
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Br F4 N2 O S'
_chemical_formula_sum            'C12 H7 Br F4 N2 O S'
_chemical_formula_weight         383.17

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'
S S 0.1246 0.1234 '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'
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                   5.4702(2)
_cell_length_b                   12.9345(8)
_cell_length_c                   19.6180(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.486(3)
_cell_angle_gamma                90
_cell_volume                     1381.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3325
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.999

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    3.171
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5905
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8941
_diffrn_reflns_av_unetI/netI     0.1204
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         31.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4413
_reflns_number_gt                2348
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0294P)²+2.2364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Br1 Br 0.24859(9) 0.06350(4) 0.80923(2) 0.03903(16) Uani 1 1 d . . . . .
S1 S 0.36103(18) 0.36915(9) 0.55780(5) 0.0231(2) Uani 1 1 d . . . . .
F1 F -0.1261(5) 0.2793(2) 0.38895(15) 0.0439(7) Uani 1 1 d . . . . .
F2 F -0.0701(7) 0.1161(3) 0.30865(18) 0.0723(11) Uani 1 1 d . . . . .
F3 F 0.6369(6) 0.0223(2) 0.43061(18) 0.0599(9) Uani 1 1 d . . . . .
F4 F 0.6206(5) 0.1832(2) 0.51473(15) 0.0460(8) Uani 1 1 d . . . . .
O1 O 0.6176(5) 0.3961(2) 0.55919(15) 0.0291(7) Uani 1 1 d . . . . .
N1 N 0.2117(6) 0.3322(3) 0.49179(18) 0.0287(8) Uani 1 1 d . . . . .
N2 N 0.2836(9) 0.0689(4) 0.3693(2) 0.0502(12) Uani 1 1 d . . . . .
C1 C 0.2482(8) 0.2428(4) 0.4560(2) 0.0292(10) Uani 1 1 d . . . . .
C2 C 0.0723(8) 0.2178(4) 0.4013(2) 0.0337(11) Uani 1 1 d . . . . .
C3 C 0.1000(10) 0.1347(4) 0.3608(3) 0.0447(13) Uani 1 1 d . . . . .
C4 C 0.4468(10) 0.0885(4) 0.4203(3) 0.0410(12) Uani 1 1 d . . . . .
C5 C 0.4406(8) 0.1720(4) 0.4646(2) 0.0331(11) Uani 1 1 d . . . . .
C6 C 0.3299(7) 0.2814(3) 0.62576(19) 0.0222(9) Uani 1 1 d . . . . .
C7 C 0.5099(8) 0.2801(4) 0.6806(2) 0.0335(11) Uani 1 1 d . . . . .
H7 H 0.649201 0.324057 0.680788 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4849(9) 0.2147(4) 0.7348(2) 0.0367(11) Uani 1 1 d . . . . .
H8 H 0.607101 0.212806 0.772636 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2803(8) 0.1517(3) 0.7338(2) 0.0272(10) Uani 1 1 d . . . . .
C10 C 0.0998(8) 0.1524(4) 0.6791(2) 0.0304(10) Uani 1 1 d . . . . .
H10 H -0.039244 0.108298 0.678913 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1264(8) 0.2185(4) 0.6250(2) 0.0311(10) Uani 1 1 d . . . . .
H11 H 0.004186 0.220590 0.587260 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1944(8) 0.4784(3) 0.5779(2) 0.0273(9) Uani 1 1 d . . . . .
H12A H 0.262260 0.505936 0.622273 0.041 Uiso 1 1 calc R U . . .
H12B H 0.022012 0.459409 0.580277 0.041 Uiso 1 1 calc R U . . .
H12C H 0.205573 0.531101 0.542458 0.041 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
Br1 C9 1.890(4) . ?
S1 O1 1.444(3) . ?
S1 N1 1.540(4) . ?
S1 C12 1.747(4) . ?
S1 C6 1.771(4) . ?
F1 C2 1.349(5) . ?
F2 C3 1.338(6) . ?
F3 C4 1.347(6) . ?
F4 C5 1.331(5) . ?
N1 C1 1.378(6) . ?
N2 C4 1.300(7) . ?
N2 C3 1.315(7) . ?
C1 C5 1.393(6) . ?
C1 C2 1.408(6) . ?
C2 C3 1.354(7) . ?
C4 C5 1.390(7) . ?
C6 C11 1.378(6) . ?
C6 C7 1.388(6) . ?
C7 C8 1.376(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 121.84(19) . . ?
O1 S1 C12 109.1(2) . . ?
N1 S1 C12 101.2(2) . . ?
O1 S1 C6 107.66(18) . . ?
N1 S1 C6 110.7(2) . . ?
C12 S1 C6 105.0(2) . . ?
C1 N1 S1 126.8(3) . . ?
C4 N2 C3 115.5(5) . . ?
N1 C1 C5 129.3(4) . . ?
N1 C1 C2 117.4(4) . . ?
C5 C1 C2 113.3(4) . . ?
F1 C2 C3 119.7(4) . . ?
F1 C2 C1 118.8(4) . . ?
C3 C2 C1 121.5(5) . . ?
N2 C3 F2 116.6(5) . . ?
N2 C3 C2 124.5(5) . . ?
F2 C3 C2 118.9(5) . . ?
N2 C4 F3 117.1(5) . . ?
N2 C4 C5 125.2(5) . . ?
F3 C4 C5 117.7(5) . . ?
F4 C5 C4 119.1(4) . . ?
F4 C5 C1 121.0(4) . . ?
C4 C5 C1 119.9(5) . . ?
C11 C6 C7 120.9(4) . . ?
C11 C6 S1 120.4(3) . . ?
C7 C6 S1 118.6(3) . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 Br1 118.6(3) . . ?
C10 C9 Br1 119.8(3) . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C6 C11 C10 120.2(4) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.640
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.123



####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2027278'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 F5 N2 O S'
_chemical_formula_sum            'C12 H7 F5 N2 O S'
_chemical_formula_weight         322.26

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'
S S 0.1246 0.1234 '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'

_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                   5.4639(2)
_cell_length_b                   12.9237(8)
_cell_length_c                   17.7393(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.726(3)
_cell_angle_gamma                90
_cell_volume                     1252.54(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2879
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7441
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2520
_reflns_number_gt                1966
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0123P)²+2.2811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2520
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.36194(13) 0.86972(6) 0.56443(4) 0.0225(2) Uani 1 1 d . . . . .
F1 F -0.0898(3) 0.78748(16) 0.38015(11) 0.0369(5) Uani 1 1 d . . . . .
F2 F -0.0283(4) 0.62045(17) 0.29259(11) 0.0485(6) Uani 1 1 d . . . . .
F3 F 0.6467(4) 0.52117(17) 0.42308(12) 0.0464(6) Uani 1 1 d . . . . .
F4 F 0.6264(3) 0.68413(16) 0.51439(11) 0.0373(5) Uani 1 1 d . . . . .
F5 F 0.2591(4) 0.55542(17) 0.79847(11) 0.0471(6) Uani 1 1 d . . . . .
O1 O 0.6185(4) 0.89688(18) 0.56243(12) 0.0313(5) Uani 1 1 d . . . . .
N1 N 0.2234(4) 0.8357(2) 0.49196(14) 0.0256(6) Uani 1 1 d . . . . .
N2 N 0.3092(5) 0.5698(2) 0.35758(15) 0.0355(7) Uani 1 1 d . . . . .
C1 C 0.2663(5) 0.7469(2) 0.45228(16) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.1006(6) 0.7235(3) 0.39350(17) 0.0266(7) Uani 1 1 d . . . . .
C3 C 0.1332(6) 0.6380(3) 0.34942(18) 0.0320(8) Uani 1 1 d . . . . .
C4 C 0.4647(6) 0.5902(3) 0.41275(19) 0.0322(8) Uani 1 1 d . . . . .
C5 C 0.4531(5) 0.6736(3) 0.46048(17) 0.0259(7) Uani 1 1 d . . . . .
C6 C 0.3227(5) 0.7762(2) 0.63662(16) 0.0212(6) Uani 1 1 d . . . . .
C7 C 0.5025(5) 0.7688(3) 0.69219(17) 0.0282(7) Uani 1 1 d . . . . .
H7 H 0.638801 0.814431 0.692509 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4794(6) 0.6935(3) 0.74727(18) 0.0328(8) Uani 1 1 d . . . . .
H8 H 0.599961 0.686121 0.785938 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2780(6) 0.6298(3) 0.74470(17) 0.0305(7) Uani 1 1 d . . . . .
C10 C 0.0955(6) 0.6377(3) 0.69064(18) 0.0295(7) Uani 1 1 d . . . . .
H10 H -0.042617 0.593096 0.691278 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1192(5) 0.7123(3) 0.63562(17) 0.0257(7) Uani 1 1 d . . . . .
H11 H -0.002810 0.719687 0.597382 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1909(6) 0.9772(2) 0.59276(18) 0.0291(7) Uani 1 1 d . . . . .
H12A H 0.254566 1.002650 0.641216 0.044 Uiso 1 1 calc R U . . .
H12B H 0.019075 0.957113 0.598134 0.044 Uiso 1 1 calc R U . . .
H12C H 0.203452 1.031946 0.554789 0.044 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 1.446(2) . ?
S1 N1 1.547(3) . ?
S1 C12 1.751(3) . ?
S1 C6 1.776(3) . ?
F1 C2 1.348(4) . ?
F2 C3 1.350(4) . ?
F3 C4 1.347(4) . ?
F4 C5 1.344(3) . ?
F5 C9 1.359(4) . ?
N1 C1 1.368(4) . ?
N2 C3 1.311(4) . ?
N2 C4 1.314(4) . ?
C1 C5 1.399(4) . ?
C1 C2 1.405(4) . ?
C2 C3 1.366(5) . ?
C4 C5 1.373(5) . ?
C6 C11 1.385(4) . ?
C6 C7 1.386(4) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 120.85(13) . . ?
O1 S1 C12 109.60(15) . . ?
N1 S1 C12 101.91(15) . . ?
O1 S1 C6 108.00(13) . . ?
N1 S1 C6 110.10(14) . . ?
C12 S1 C6 105.26(15) . . ?
C1 N1 S1 125.5(2) . . ?
C3 N2 C4 114.4(3) . . ?
N1 C1 C5 130.1(3) . . ?
N1 C1 C2 116.7(3) . . ?
C5 C1 C2 113.2(3) . . ?
F1 C2 C3 120.1(3) . . ?
F1 C2 C1 119.1(3) . . ?
C3 C2 C1 120.8(3) . . ?
N2 C3 F2 116.2(3) . . ?
N2 C3 C2 125.5(3) . . ?
F2 C3 C2 118.3(3) . . ?
N2 C4 F3 116.0(3) . . ?
N2 C4 C5 125.6(3) . . ?
F3 C4 C5 118.4(3) . . ?
F4 C5 C4 118.7(3) . . ?
F4 C5 C1 120.8(3) . . ?
C4 C5 C1 120.5(3) . . ?
C11 C6 C7 122.0(3) . . ?
C11 C6 S1 120.1(2) . . ?
C7 C6 S1 118.0(2) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 118.5(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
F5 C9 C8 117.9(3) . . ?
F5 C9 C10 118.7(3) . . ?
C8 C9 C10 123.4(3) . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C10 C11 C6 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2027279'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3c
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Cl F4 N2 O S'
_chemical_formula_sum            'C12 H7 Cl F4 N2 O S'
_chemical_formula_weight         338.71

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                   16.7926(8)
_cell_length_b                   12.4383(5)
_cell_length_c                   13.0356(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.400(5)
_cell_angle_gamma                90
_cell_volume                     2568.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4685
_cell_measurement_theta_min      2.0920
_cell_measurement_theta_max      28.6560

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.508
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9917
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4623
_reflns_number_gt                3925
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0244P)²+4.6690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4623
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
S1 S -0.04109(4) 0.54235(6) 0.19686(6) 0.01896(17) Uani 1 1 d . . . . .
Cl1 Cl 0.10040(5) 0.70477(6) 0.36475(6) 0.02711(19) Uani 1 1 d . . . . .
F1 F 0.12422(11) 0.74397(14) 0.11478(15) 0.0285(4) Uani 1 1 d . . . . .
F2 F 0.26503(11) 0.68195(17) 0.07535(15) 0.0352(5) Uani 1 1 d . . . . .
F3 F 0.20304(12) 0.33026(16) 0.09104(17) 0.0404(5) Uani 1 1 d . . . . .
F4 F 0.05886(11) 0.37448(14) 0.12745(14) 0.0289(4) Uani 1 1 d . . . . .
O1 O -0.09426(12) 0.45050(17) 0.15226(17) 0.0249(5) Uani 1 1 d . . . . .
N1 N 0.00922(14) 0.5997(2) 0.13389(19) 0.0199(5) Uani 1 1 d . . . . .
N2 N 0.23480(15) 0.5064(3) 0.0846(2) 0.0299(7) Uani 1 1 d . . . . .
C1 C 0.08373(17) 0.5619(2) 0.1224(2) 0.0191(6) Uani 1 1 d . . . . .
C2 C 0.14053(18) 0.6384(3) 0.1090(2) 0.0217(7) Uani 1 1 d . . . . .
C3 C 0.21229(18) 0.6070(3) 0.0900(2) 0.0269(7) Uani 1 1 d . . . . .
C4 C 0.1823(2) 0.4345(3) 0.0980(2) 0.0286(8) Uani 1 1 d . . . . .
C5 C 0.10832(18) 0.4563(2) 0.1165(2) 0.0215(7) Uani 1 1 d . . . . .
C6 C 0.02679(17) 0.5047(2) 0.3295(2) 0.0190(6) Uani 1 1 d . . . . .
C7 C 0.08813(18) 0.5723(2) 0.3979(2) 0.0214(6) Uani 1 1 d . . . . .
C8 C 0.14109(18) 0.5344(2) 0.4964(2) 0.0219(7) Uani 1 1 d . . . . .
H8 H 0.182739 0.580251 0.543138 0.026 Uiso 1 1 calc R U . . .
C9 C 0.13335(19) 0.4291(3) 0.5270(2) 0.0265(7) Uani 1 1 d . . . . .
H9 H 0.170899 0.402529 0.593934 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0714(2) 0.3624(3) 0.4609(3) 0.0276(7) Uani 1 1 d . . . . .
H10 H 0.065684 0.290896 0.483129 0.033 Uiso 1 1 calc R U . . .
C11 C 0.01807(18) 0.4002(2) 0.3627(2) 0.0229(7) Uani 1 1 d . . . . .
H11 H -0.024801 0.354807 0.317504 0.028 Uiso 1 1 calc R U . . .
C12 C -0.10605(19) 0.6465(3) 0.2142(3) 0.0259(7) Uani 1 1 d . . . . .
H12A H -0.136650 0.678617 0.143365 0.039 Uiso 1 1 calc R U . . .
H12B H -0.071212 0.701532 0.262313 0.039 Uiso 1 1 calc R U . . .
H12C H -0.146543 0.617537 0.246511 0.039 Uiso 1 1 calc R U . . .
S2 S 0.48609(4) 0.29682(6) 0.78420(6) 0.02321(18) Uani 1 1 d . . . . .
Cl2 Cl 0.57229(5) 0.45448(7) 0.64449(7) 0.0337(2) Uani 1 1 d . . . . .
F5 F 0.41217(12) 0.13970(16) 0.61293(18) 0.0459(6) Uani 1 1 d . . . . .
F6 F 0.32432(14) 0.10001(19) 0.40532(19) 0.0550(6) Uani 1 1 d . . . . .
F7 F 0.24280(12) 0.4452(2) 0.34080(15) 0.0452(6) Uani 1 1 d . . . . .
F8 F 0.33136(11) 0.50347(15) 0.54534(15) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.46523(13) 0.20612(18) 0.83959(19) 0.0323(5) Uani 1 1 d . . . . .
N3 N 0.41665(15) 0.3595(2) 0.6969(2) 0.0234(6) Uani 1 1 d . . . . .
N4 N 0.28336(17) 0.2732(3) 0.3724(2) 0.0384(8) Uani 1 1 d . . . . .
C13 C 0.37697(17) 0.3246(3) 0.5918(2) 0.0234(7) Uani 1 1 d . . . . .
C14 C 0.37331(19) 0.2209(3) 0.5500(3) 0.0311(8) Uani 1 1 d . . . . .
C15 C 0.3263(2) 0.2021(3) 0.4417(3) 0.0378(9) Uani 1 1 d . . . . .
C16 C 0.28735(19) 0.3700(3) 0.4114(3) 0.0322(8) Uani 1 1 d . . . . .
C17 C 0.33226(18) 0.4002(3) 0.5152(2) 0.0257(7) Uani 1 1 d . . . . .
C18 C 0.56873(17) 0.2562(2) 0.7343(2) 0.0210(7) Uani 1 1 d . . . . .
C19 C 0.60450(18) 0.3225(3) 0.6755(3) 0.0248(7) Uani 1 1 d . . . . .
C20 C 0.66947(19) 0.2833(3) 0.6421(3) 0.0267(7) Uani 1 1 d . . . . .
H20 H 0.694485 0.328214 0.602298 0.032 Uiso 1 1 calc R U . . .
C21 C 0.69781(19) 0.1784(3) 0.6670(3) 0.0279(7) Uani 1 1 d . . . . .
H21 H 0.742574 0.151999 0.644682 0.034 Uiso 1 1 calc R U . . .
C22 C 0.66142(19) 0.1124(3) 0.7238(2) 0.0257(7) Uani 1 1 d . . . . .
H22 H 0.680527 0.040432 0.739439 0.031 Uiso 1 1 calc R U . . .
C23 C 0.59711(18) 0.1506(3) 0.7581(2) 0.0231(7) Uani 1 1 d . . . . .
H23 H 0.572340 0.105184 0.797796 0.028 Uiso 1 1 calc R U . . .
C24 C 0.53119(19) 0.3975(3) 0.8808(3) 0.0291(7) Uani 1 1 d . . . . .
H24A H 0.486998 0.431680 0.903110 0.044 Uiso 1 1 calc R U . . .
H24B H 0.558251 0.451528 0.848645 0.044 Uiso 1 1 calc R U . . .
H24C H 0.573464 0.365269 0.944349 0.044 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 1.448(2) . ?
S1 N1 1.536(2) . ?
S1 C12 1.756(3) . ?
S1 C6 1.789(3) . ?
Cl1 C7 1.733(3) . ?
F1 C2 1.348(4) . ?
F2 C3 1.343(4) . ?
F3 C4 1.354(4) . ?
F4 C5 1.350(3) . ?
N1 C1 1.391(4) . ?
N2 C4 1.307(4) . ?
N2 C3 1.315(4) . ?
C1 C5 1.387(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.365(4) . ?
C4 C5 1.369(4) . ?
C6 C11 1.393(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.379(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S2 O2 1.444(2) . ?
S2 N3 1.543(3) . ?
S2 C24 1.758(3) . ?
S2 C18 1.790(3) . ?
Cl2 C19 1.734(3) . ?
F5 C14 1.328(4) . ?
F6 C15 1.352(4) . ?
F7 C16 1.350(4) . ?
F8 C17 1.345(4) . ?
N3 C13 1.379(4) . ?
N4 C15 1.298(5) . ?
N4 C16 1.300(5) . ?
C13 C14 1.394(5) . ?
C13 C17 1.396(4) . ?
C14 C15 1.389(5) . ?
C16 C17 1.365(4) . ?
C18 C19 1.391(4) . ?
C18 C23 1.396(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.390(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 N1 121.85(13) . . ?
O1 S1 C12 107.90(14) . . ?
N1 S1 C12 101.61(14) . . ?
O1 S1 C6 106.96(13) . . ?
N1 S1 C6 110.58(13) . . ?
C12 S1 C6 107.01(14) . . ?
C1 N1 S1 125.1(2) . . ?
C4 N2 C3 115.1(3) . . ?
C5 C1 N1 128.4(3) . . ?
C5 C1 C2 114.2(3) . . ?
N1 C1 C2 117.3(3) . . ?
F1 C2 C3 119.8(3) . . ?
F1 C2 C1 119.7(3) . . ?
C3 C2 C1 120.5(3) . . ?
N2 C3 F2 116.0(3) . . ?
N2 C3 C2 124.7(3) . . ?
F2 C3 C2 119.3(3) . . ?
N2 C4 F3 116.5(3) . . ?
N2 C4 C5 125.4(3) . . ?
F3 C4 C5 118.0(3) . . ?
F4 C5 C4 119.7(3) . . ?
F4 C5 C1 120.2(3) . . ?
C4 C5 C1 120.1(3) . . ?
C11 C6 C7 119.6(3) . . ?
C11 C6 S1 116.5(2) . . ?
C7 C6 S1 123.9(2) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 Cl1 117.6(2) . . ?
C6 C7 Cl1 122.4(2) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S2 N3 120.95(14) . . ?
O2 S2 C24 108.46(15) . . ?
N3 S2 C24 102.04(15) . . ?
O2 S2 C18 107.88(14) . . ?
N3 S2 C18 111.21(14) . . ?
C24 S2 C18 105.04(15) . . ?
C13 N3 S2 124.8(2) . . ?
C15 N4 C16 114.5(3) . . ?
N3 C13 C14 128.6(3) . . ?
N3 C13 C17 117.8(3) . . ?
C14 C13 C17 113.6(3) . . ?
F5 C14 C15 119.8(3) . . ?
F5 C14 C13 120.9(3) . . ?
C15 C14 C13 119.3(3) . . ?
N4 C15 F6 116.9(3) . . ?
N4 C15 C14 126.0(3) . . ?
F6 C15 C14 117.0(4) . . ?
N4 C16 F7 115.5(3) . . ?
N4 C16 C17 125.6(3) . . ?
F7 C16 C17 118.9(3) . . ?
F8 C17 C16 119.8(3) . . ?
F8 C17 C13 119.3(3) . . ?
C16 C17 C13 120.8(3) . . ?
C19 C18 C23 120.1(3) . . ?
C19 C18 S2 124.2(2) . . ?
C23 C18 S2 115.7(2) . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 Cl2 118.4(2) . . ?
C18 C19 Cl2 122.1(2) . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_3i
_database_code_depnum_ccdc_archive 'CCDC 2027284'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3i
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 F4 I N2 O S'
_chemical_formula_sum            'C12 H7 F4 I N2 O S'
_chemical_formula_weight         430.16

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.2874(4)
_cell_length_b                   9.4153(8)
_cell_length_c                   14.7672(13)
_cell_angle_alpha                80.054(2)
_cell_angle_beta                 85.332(3)
_cell_angle_gamma                79.389(2)
_cell_volume                     710.78(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1436
_cell_measurement_theta_min      2.2260
_cell_measurement_theta_max      24.9740

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.443
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4486
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_full        25.199
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2543
_reflns_number_gt                1746
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2543
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
I1 I 0.43592(13) 0.81659(7) 0.43084(4) 0.0612(3) Uani 1 1 d . . . . .
S1 S 0.1831(3) 0.52011(17) 0.85992(12) 0.0230(4) Uani 1 1 d . . . . .
F1 F 0.0108(7) 0.3128(4) 0.7609(3) 0.0410(11) Uani 1 1 d . . . . .
F2 F 0.0638(8) 0.0421(5) 0.7229(3) 0.0456(12) Uani 1 1 d . . . . .
F3 F 0.7308(7) 0.1430(4) 0.9471(3) 0.0362(10) Uani 1 1 d . . . . .
F4 F 0.7558(8) -0.1174(4) 0.8952(3) 0.0459(12) Uani 1 1 d . . . . .
O1 O -0.0926(8) 0.5312(5) 0.8745(3) 0.0287(11) Uani 1 1 d . . . . .
N1 N 0.3638(10) 0.3737(6) 0.8885(4) 0.0263(13) Uani 1 1 d . . . . .
N2 N 0.4146(12) -0.0388(7) 0.8076(5) 0.0370(16) Uani 1 1 d . . . . .
C1 C 0.3662(12) 0.2434(7) 0.8576(5) 0.0234(15) Uani 1 1 d . . . . .
C2 C 0.1985(13) 0.2109(8) 0.7979(5) 0.0317(18) Uani 1 1 d . . . . .
C3 C 0.2331(14) 0.0696(9) 0.7789(5) 0.0333(18) Uani 1 1 d . . . . .
C4 C 0.5703(14) -0.0075(8) 0.8634(5) 0.0321(18) Uani 1 1 d . . . . .
C5 C 0.5582(13) 0.1254(8) 0.8900(5) 0.0288(17) Uani 1 1 d . . . . .
C6 C 0.2921(11) 0.6352(7) 0.9226(5) 0.0210(15) Uani 1 1 d . . . . .
H6A H 0.197623 0.735133 0.906493 0.032 Uiso 1 1 calc R U . . .
H6B H 0.476553 0.634153 0.908123 0.032 Uiso 1 1 calc R U . . .
H6C H 0.263488 0.601140 0.988585 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2489(12) 0.5946(7) 0.7424(5) 0.0257(16) Uani 1 1 d . . . . .
C8 C 0.4822(13) 0.5453(8) 0.6981(5) 0.0349(18) Uani 1 1 d . . . . .
H8 H 0.604815 0.469703 0.729091 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5333(13) 0.6074(8) 0.6089(5) 0.0355(19) Uani 1 1 d . . . . .
H9 H 0.691386 0.574749 0.577303 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3530(15) 0.7176(8) 0.5657(5) 0.0360(19) Uani 1 1 d . . . . .
C11 C 0.1202(15) 0.7652(8) 0.6095(6) 0.040(2) Uani 1 1 d . . . . .
H11 H -0.000785 0.841671 0.578422 0.048 Uiso 1 1 calc R U . . .
C12 C 0.0633(14) 0.7025(8) 0.6979(5) 0.0324(18) Uani 1 1 d . . . . .
H12 H -0.098905 0.731897 0.727996 0.039 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 C10 2.097(7) . ?
S1 O1 1.443(5) . ?
S1 N1 1.540(6) . ?
S1 C6 1.740(7) . ?
S1 C7 1.787(7) . ?
F1 C2 1.327(8) . ?
F2 C3 1.353(8) . ?
F3 C5 1.342(8) . ?
F4 C4 1.336(8) . ?
N1 C1 1.379(9) . ?
N2 C3 1.304(10) . ?
N2 C4 1.314(10) . ?
C1 C5 1.405(10) . ?
C1 C2 1.406(10) . ?
C2 C3 1.383(11) . ?
C4 C5 1.364(10) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.389(9) . ?
C7 C12 1.391(10) . ?
C8 C9 1.372(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(10) . ?
C11 C12 1.370(11) . ?
C11 H11 0.9500 . ?
C12 H12 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 N1 120.7(3) . . ?
O1 S1 C6 109.8(3) . . ?
N1 S1 C6 102.0(3) . . ?
O1 S1 C7 107.7(3) . . ?
N1 S1 C7 111.1(3) . . ?
C6 S1 C7 104.3(3) . . ?
C1 N1 S1 126.9(5) . . ?
C3 N2 C4 114.3(6) . . ?
N1 C1 C5 116.8(6) . . ?
N1 C1 C2 128.6(7) . . ?
C5 C1 C2 114.6(6) . . ?
F1 C2 C3 120.6(7) . . ?
F1 C2 C1 121.0(7) . . ?
C3 C2 C1 118.4(7) . . ?
N2 C3 F2 116.7(7) . . ?
N2 C3 C2 126.8(7) . . ?
F2 C3 C2 116.5(7) . . ?
N2 C4 F4 115.6(6) . . ?
N2 C4 C5 125.7(7) . . ?
F4 C4 C5 118.7(7) . . ?
F3 C5 C4 119.7(7) . . ?
F3 C5 C1 120.1(6) . . ?
C4 C5 C1 120.1(7) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 121.6(7) . . ?
C8 C7 S1 119.9(5) . . ?
C12 C7 S1 118.5(5) . . ?
C9 C8 C7 119.1(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.3(7) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 121.5(7) . . ?
C9 C10 I1 119.3(5) . . ?
C11 C10 I1 119.2(6) . . ?
C12 C11 C10 120.1(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 118.3(7) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?

_refine_diff_density_max         1.375
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.140



####################################################################### 
# 
# 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_3o
_database_code_depnum_ccdc_archive 'CCDC 2027291'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3o
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 F4 N3 O S'
_chemical_formula_sum            'C11 H7 F4 N3 O S'
_chemical_formula_weight         305.26

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                   5.7613(2)
_cell_length_b                   12.7432(3)
_cell_length_c                   15.8339(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.519(2)
_cell_angle_gamma                90
_cell_volume                     1158.87(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1649
_cell_measurement_theta_min      3.1860
_cell_measurement_theta_max      27.7020

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3644
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         25.747
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2172
_reflns_number_gt                1853
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0363P)²+0.4765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2172
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
S1 S 0.38050(8) 0.37473(4) 0.57733(3) 0.01530(16) Uani 1 1 d . . . . .
F1 F -0.0821(2) 0.27858(9) 0.37627(7) 0.0219(3) Uani 1 1 d . . . . .
F2 F -0.0399(2) 0.10449(10) 0.28306(8) 0.0255(3) Uani 1 1 d . . . . .
F3 F 0.6544(2) 0.02394(10) 0.42023(8) 0.0293(3) Uani 1 1 d . . . . .
F4 F 0.6529(2) 0.19545(10) 0.51660(7) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.6264(2) 0.40063(12) 0.58776(9) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.2591(3) 0.34372(13) 0.49049(10) 0.0177(4) Uani 1 1 d . . . . .
N2 N 0.3085(3) 0.06412(14) 0.35093(11) 0.0207(4) Uani 1 1 d . . . . .
N3 N 0.4788(3) 0.16071(14) 0.76192(11) 0.0202(4) Uani 1 1 d . . . . .
C1 C 0.2859(4) 0.24880(16) 0.45046(12) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.1090(4) 0.21823(16) 0.38957(13) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.1307(4) 0.12955(17) 0.34272(13) 0.0192(5) Uani 1 1 d . . . . .
C4 C 0.4727(4) 0.09020(17) 0.40930(13) 0.0193(5) Uani 1 1 d . . . . .
C5 C 0.4722(4) 0.17768(17) 0.45934(13) 0.0176(5) Uani 1 1 d . . . . .
C6 C 0.2164(4) 0.48407(16) 0.60374(13) 0.0204(5) Uani 1 1 d . . . . .
H6A H 0.276806 0.511163 0.659095 0.031 Uiso 1 1 calc R U . . .
H6B H 0.053219 0.463434 0.606185 0.031 Uiso 1 1 calc R U . . .
H6C H 0.227483 0.538736 0.560714 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3272(3) 0.27425(16) 0.65077(12) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.5040(4) 0.24148(16) 0.70922(13) 0.0175(4) Uani 1 1 d . . . . .
H8 H 0.648547 0.277656 0.712037 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2710(4) 0.11306(17) 0.75713(13) 0.0197(5) Uani 1 1 d . . . . .
H9 H 0.250256 0.055649 0.794067 0.024 Uiso 1 1 calc R U . . .
C10 C 0.0842(4) 0.14238(17) 0.70156(13) 0.0190(5) Uani 1 1 d . . . . .
H10 H -0.060436 0.106549 0.701450 0.023 Uiso 1 1 calc R U . . .
C11 C 0.1118(3) 0.22428(16) 0.64656(13) 0.0170(4) Uani 1 1 d . . . . .
H11 H -0.011714 0.245926 0.607136 0.020 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 1.4514(14) . ?
S1 N1 1.5442(17) . ?
S1 C6 1.753(2) . ?
S1 C7 1.773(2) . ?
F1 C2 1.346(2) . ?
F2 C3 1.347(2) . ?
F3 C4 1.345(2) . ?
F4 C5 1.345(2) . ?
N1 C1 1.380(3) . ?
N2 C4 1.312(3) . ?
N2 C3 1.319(3) . ?
N3 C9 1.339(3) . ?
N3 C8 1.340(3) . ?
C1 C2 1.402(3) . ?
C1 C5 1.403(3) . ?
C2 C3 1.363(3) . ?
C4 C5 1.368(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.385(3) . ?
C7 C11 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 H11 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 N1 121.94(9) . . ?
O1 S1 C6 109.40(10) . . ?
N1 S1 C6 101.59(10) . . ?
O1 S1 C7 107.91(9) . . ?
N1 S1 C7 108.03(10) . . ?
C6 S1 C7 107.04(10) . . ?
C1 N1 S1 125.04(15) . . ?
C4 N2 C3 114.86(18) . . ?
C9 N3 C8 116.94(19) . . ?
N1 C1 C2 117.24(18) . . ?
N1 C1 C5 129.23(19) . . ?
C2 C1 C5 113.48(19) . . ?
F1 C2 C3 119.85(19) . . ?
F1 C2 C1 119.36(18) . . ?
C3 C2 C1 120.77(19) . . ?
N2 C3 F2 115.94(18) . . ?
N2 C3 C2 125.1(2) . . ?
F2 C3 C2 119.01(19) . . ?
N2 C4 F3 116.24(19) . . ?
N2 C4 C5 125.5(2) . . ?
F3 C4 C5 118.30(19) . . ?
F4 C5 C4 119.41(18) . . ?
F4 C5 C1 120.27(18) . . ?
C4 C5 C1 120.31(19) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C11 119.99(19) . . ?
C8 C7 S1 119.98(16) . . ?
C11 C7 S1 119.93(16) . . ?
N3 C8 C7 122.52(19) . . ?
N3 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
N3 C9 C10 124.0(2) . . ?
N3 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C11 C10 C9 118.88(19) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C7 117.64(19) . . ?
C10 C11 H11 121.2 . . ?
C7 C11 H11 121.2 . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 2027285'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3j
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F4 N2 O2 S'
_chemical_formula_sum            'C13 H10 F4 N2 O2 S'
_chemical_formula_weight         334.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.0962(8)
_cell_length_b                   8.3321(4)
_cell_length_c                   13.6279(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.839(6)
_cell_angle_gamma                90
_cell_volume                     1363.74(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3577
_cell_measurement_theta_min      2.4040
_cell_measurement_theta_max      29.2710

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8887
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2749
_reflns_number_gt                2208
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0363P)²+0.7061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2749
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
S1 S 0.18332(4) 0.08789(6) 0.46854(4) 0.02137(14) Uani 1 1 d . . . . .
F1 F 0.38179(10) 0.32495(14) 0.29595(8) 0.0289(3) Uani 1 1 d . . . . .
F2 F 0.57967(10) 0.45811(14) 0.35889(9) 0.0335(3) Uani 1 1 d . . . . .
F3 F 0.59389(10) 0.21710(17) 0.65693(9) 0.0401(3) Uani 1 1 d . . . . .
F4 F 0.40074(10) 0.06214(14) 0.60572(9) 0.0328(3) Uani 1 1 d . . . . .
O1 O 0.17607(12) -0.05363(16) 0.52930(10) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.16360(12) 0.42211(16) 0.40386(10) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.28297(13) 0.11076(19) 0.40908(12) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.58801(13) 0.3355(2) 0.50747(13) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.38114(16) 0.1839(2) 0.44733(14) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.43267(16) 0.2886(2) 0.38626(14) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.53296(16) 0.3568(2) 0.41932(15) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.54034(17) 0.2390(3) 0.56581(15) 0.0275(5) Uani 1 1 d . . . . .
C5 C 0.44064(17) 0.1618(2) 0.54039(14) 0.0245(4) Uani 1 1 d . . . . .
C6 C 0.16693(15) 0.2578(2) 0.54331(13) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.15909(15) 0.4124(2) 0.50251(14) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.14767(15) 0.5431(2) 0.56401(15) 0.0226(4) Uani 1 1 d . . . . .
H8 H 0.140519 0.648458 0.537426 0.027 Uiso 1 1 calc R U . . .
C9 C 0.14684(15) 0.5180(2) 0.66457(14) 0.0238(4) Uani 1 1 d . . . . .
H9 H 0.139135 0.607408 0.706449 0.029 Uiso 1 1 calc R U . . .
C10 C 0.15698(16) 0.3654(2) 0.70544(14) 0.0239(4) Uani 1 1 d . . . . .
H10 H 0.157711 0.350903 0.774658 0.029 Uiso 1 1 calc R U . . .
C11 C 0.16600(15) 0.2348(2) 0.64447(14) 0.0202(4) Uani 1 1 d . . . . .
H11 H 0.171557 0.129555 0.671441 0.024 Uiso 1 1 calc R U . . .
C12 C 0.15471(18) 0.5770(2) 0.35761(16) 0.0301(5) Uani 1 1 d . . . . .
H12A H 0.081434 0.623082 0.364245 0.045 Uiso 1 1 calc R U . . .
H12B H 0.163671 0.565945 0.287398 0.045 Uiso 1 1 calc R U . . .
H12C H 0.212943 0.647727 0.389581 0.045 Uiso 1 1 calc R U . . .
C13 C 0.06923(17) 0.0862(3) 0.37590(15) 0.0290(5) Uani 1 1 d . . . . .
H13A H 0.076133 -0.004791 0.331438 0.044 Uiso 1 1 calc R U . . .
H13B H 0.067739 0.186483 0.338241 0.044 Uiso 1 1 calc R U . . .
H13C H 0.000134 0.075795 0.406330 0.044 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 1.4494(14) . ?
S1 N1 1.5422(15) . ?
S1 C13 1.756(2) . ?
S1 C6 1.7694(18) . ?
F1 C2 1.343(2) . ?
F2 C3 1.349(2) . ?
F3 C4 1.343(2) . ?
F4 C5 1.348(2) . ?
O2 C7 1.354(2) . ?
O2 C12 1.435(2) . ?
N1 C1 1.381(3) . ?
N2 C4 1.312(3) . ?
N2 C3 1.314(3) . ?
C1 C5 1.394(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.367(3) . ?
C4 C5 1.374(3) . ?
C6 C11 1.393(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N1 120.32(9) . . ?
O1 S1 C13 107.95(10) . . ?
N1 S1 C13 102.70(9) . . ?
O1 S1 C6 107.67(8) . . ?
N1 S1 C6 110.60(9) . . ?
C13 S1 C6 106.75(10) . . ?
C7 O2 C12 118.69(15) . . ?
C1 N1 S1 123.18(13) . . ?
C4 N2 C3 115.18(18) . . ?
N1 C1 C5 127.80(18) . . ?
N1 C1 C2 118.28(18) . . ?
C5 C1 C2 113.85(18) . . ?
F1 C2 C3 120.01(17) . . ?
F1 C2 C1 119.77(17) . . ?
C3 C2 C1 120.20(18) . . ?
N2 C3 F2 116.04(18) . . ?
N2 C3 C2 125.33(18) . . ?
F2 C3 C2 118.60(18) . . ?
N2 C4 F3 116.44(19) . . ?
N2 C4 C5 124.75(19) . . ?
F3 C4 C5 118.81(18) . . ?
F4 C5 C4 119.61(18) . . ?
F4 C5 C1 119.70(18) . . ?
C4 C5 C1 120.68(18) . . ?
C11 C6 C7 120.73(17) . . ?
C11 C6 S1 118.31(14) . . ?
C7 C6 S1 120.92(14) . . ?
O2 C7 C8 124.75(17) . . ?
O2 C7 C6 116.09(16) . . ?
C8 C7 C6 119.16(17) . . ?
C9 C8 C7 119.35(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 121.59(18) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C11 C10 C9 119.33(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C6 119.81(18) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_3l
_database_code_depnum_ccdc_archive 'CCDC 2027288'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3l
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F4 N2 O S'
_chemical_formula_sum            'C13 H10 F4 N2 O S'
_chemical_formula_weight         318.29

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'

_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                   5.5302(2)
_cell_length_b                   13.7424(9)
_cell_length_c                   18.1828(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.431(3)
_cell_angle_gamma                90
_cell_volume                     1381.43(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3138
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.131

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6292
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7694
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.241
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2768
_reflns_number_gt                1617
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0345P)²+1.5609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
S1 S 0.36122(16) 0.63097(8) 0.55489(5) 0.0389(3) Uani 1 1 d . . . . .
F1 F -0.0837(5) 0.7006(2) 0.37200(14) 0.0677(8) Uani 1 1 d . . . . .
F2 F -0.0279(6) 0.8553(3) 0.28468(16) 0.1007(12) Uani 1 1 d . . . . .
F3 F 0.6379(6) 0.9533(3) 0.4110(2) 0.1083(13) Uani 1 1 d . . . . .
F4 F 0.6261(5) 0.8016(2) 0.50137(15) 0.0745(9) Uani 1 1 d . . . . .
O1 O 0.6117(4) 0.6010(2) 0.55553(15) 0.0507(8) Uani 1 1 d . . . . .
N1 N 0.2301(6) 0.6595(3) 0.48229(17) 0.0435(9) Uani 1 1 d . . . . .
N2 N 0.3024(9) 0.9054(4) 0.3478(2) 0.0767(13) Uani 1 1 d . . . . .
C1 C 0.2687(7) 0.7424(3) 0.4426(2) 0.0437(10) Uani 1 1 d . . . . .
C2 C 0.1034(8) 0.7615(4) 0.3840(2) 0.0512(11) Uani 1 1 d . . . . .
C3 C 0.1315(10) 0.8407(4) 0.3406(3) 0.0647(14) Uani 1 1 d . . . . .
C4 C 0.4578(10) 0.8890(4) 0.4022(3) 0.0701(15) Uani 1 1 d . . . . .
C5 C 0.4533(8) 0.8110(4) 0.4488(2) 0.0554(13) Uani 1 1 d . . . . .
C6 C 0.1842(7) 0.5337(3) 0.5844(2) 0.0473(11) Uani 1 1 d . . . . .
H6A H 0.199057 0.479150 0.550066 0.071 Uiso 1 1 calc R U . . .
H6B H 0.014581 0.554159 0.585899 0.071 Uiso 1 1 calc R U . . .
H6C H 0.239588 0.513356 0.633597 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3291(6) 0.7225(3) 0.6218(2) 0.0358(9) Uani 1 1 d . . . . .
C8 C 0.5073(7) 0.7324(3) 0.6760(2) 0.0440(10) Uani 1 1 d . . . . .
H8 H 0.642474 0.689772 0.677650 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4859(8) 0.8049(4) 0.7276(2) 0.0514(12) Uani 1 1 d . . . . .
H9 H 0.607435 0.811446 0.765136 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2921(7) 0.8686(3) 0.7262(2) 0.0428(10) Uani 1 1 d . . . . .
C11 C 0.1149(7) 0.8566(3) 0.6716(2) 0.0472(11) Uani 1 1 d . . . . .
H11 H -0.020765 0.899028 0.670260 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1312(7) 0.7847(3) 0.6195(2) 0.0463(11) Uani 1 1 d . . . . .
H12 H 0.008602 0.777580 0.582399 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2773(9) 0.9507(4) 0.7813(3) 0.0639(14) Uani 1 1 d . . . . .
H13A H 0.333119 0.927618 0.829776 0.096 Uiso 1 1 calc R U . . .
H13B H 0.109440 0.972986 0.783971 0.096 Uiso 1 1 calc R U . . .
H13C H 0.379829 1.004722 0.765720 0.096 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 1.445(3) . ?
S1 N1 1.541(3) . ?
S1 C6 1.749(4) . ?
S1 C7 1.762(4) . ?
F1 C2 1.344(5) . ?
F2 C3 1.345(5) . ?
F3 C4 1.339(6) . ?
F4 C5 1.341(5) . ?
N1 C1 1.368(5) . ?
N2 C3 1.302(6) . ?
N2 C4 1.312(6) . ?
C1 C5 1.392(6) . ?
C1 C2 1.412(5) . ?
C2 C3 1.354(7) . ?
C4 C5 1.367(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.383(5) . ?
C7 C12 1.388(5) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(5) . ?
C10 C13 1.511(6) . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N1 120.65(18) . . ?
O1 S1 C6 108.90(19) . . ?
N1 S1 C6 101.63(19) . . ?
O1 S1 C7 108.11(17) . . ?
N1 S1 C7 110.91(19) . . ?
C6 S1 C7 105.51(19) . . ?
C1 N1 S1 126.0(3) . . ?
C3 N2 C4 114.7(5) . . ?
N1 C1 C5 130.2(4) . . ?
N1 C1 C2 116.5(4) . . ?
C5 C1 C2 113.2(4) . . ?
F1 C2 C3 120.4(4) . . ?
F1 C2 C1 119.2(4) . . ?
C3 C2 C1 120.5(4) . . ?
N2 C3 F2 115.8(5) . . ?
N2 C3 C2 125.7(5) . . ?
F2 C3 C2 118.5(5) . . ?
N2 C4 F3 116.6(5) . . ?
N2 C4 C5 125.4(5) . . ?
F3 C4 C5 117.9(5) . . ?
F4 C5 C4 119.6(4) . . ?
F4 C5 C1 120.0(4) . . ?
C4 C5 C1 120.4(4) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 120.5(4) . . ?
C8 C7 S1 118.7(3) . . ?
C12 C7 S1 120.8(3) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.7(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 118.1(4) . . ?
C9 C10 C13 121.0(4) . . ?
C11 C10 C13 120.9(4) . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_3j_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2027286'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3j
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F4 N2 O2 S'
_chemical_formula_sum            'C13 H10 F4 N2 O2 S'
_chemical_formula_weight         334.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.2106(9)
_cell_length_b                   8.3555(6)
_cell_length_c                   13.7645(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.208(4)
_cell_angle_gamma                90
_cell_volume                     1396.10(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2708
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6164
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7566
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.119
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2794
_reflns_number_gt                1385
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0428P)²+1.0539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2794
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
S1 S 0.18382(11) 0.91062(13) 0.46858(8) 0.0507(4) Uani 1 1 d . . . . .
F1 F 0.3860(3) 0.6795(3) 0.29877(17) 0.0656(9) Uani 1 1 d . . . . .
F2 F 0.5809(3) 0.5480(3) 0.3606(2) 0.0782(10) Uani 1 1 d . . . . .
F3 F 0.5873(3) 0.7845(4) 0.6558(2) 0.0938(11) Uani 1 1 d . . . . .
F4 F 0.3964(3) 0.9360(3) 0.60469(19) 0.0733(9) Uani 1 1 d . . . . .
O1 O 0.1749(3) 1.0505(3) 0.5287(2) 0.0648(11) Uani 1 1 d . . . . .
O2 O 0.1648(3) 0.5779(3) 0.4049(2) 0.0582(10) Uani 1 1 d . . . . .
N1 N 0.2840(3) 0.8878(4) 0.4102(2) 0.0515(11) Uani 1 1 d . . . . .
N2 N 0.5848(4) 0.6681(5) 0.5078(3) 0.0648(12) Uani 1 1 d . . . . .
C1 C 0.3804(4) 0.8163(5) 0.4493(3) 0.0453(12) Uani 1 1 d . . . . .
C2 C 0.4343(5) 0.7141(5) 0.3891(3) 0.0490(13) Uani 1 1 d . . . . .
C3 C 0.5338(5) 0.6482(6) 0.4211(4) 0.0545(14) Uani 1 1 d . . . . .
C4 C 0.5360(5) 0.7619(7) 0.5660(4) 0.0619(15) Uani 1 1 d . . . . .
C5 C 0.4375(5) 0.8373(6) 0.5408(3) 0.0551(14) Uani 1 1 d . . . . .
C6 C 0.0722(5) 0.9121(6) 0.3760(3) 0.0680(16) Uani 1 1 d . . . . .
H6A H 0.003093 0.922522 0.405603 0.102 Uiso 1 1 calc R U . . .
H6B H 0.071534 0.812020 0.338854 0.102 Uiso 1 1 calc R U . . .
H6C H 0.079960 1.002746 0.332040 0.102 Uiso 1 1 calc R U . . .
C7 C 0.1658(4) 0.7415(5) 0.5420(3) 0.0393(11) Uani 1 1 d . . . . .
C8 C 0.1633(4) 0.7636(5) 0.6414(3) 0.0473(12) Uani 1 1 d . . . . .
H8 H 0.167878 0.868617 0.667940 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1544(4) 0.6341(6) 0.7019(3) 0.0544(14) Uani 1 1 d . . . . .
H9 H 0.154091 0.648832 0.770348 0.065 Uiso 1 1 calc R U . . .
C10 C 0.1459(4) 0.4827(6) 0.6617(4) 0.0572(14) Uani 1 1 d . . . . .
H10 H 0.137831 0.393449 0.703120 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1487(4) 0.4577(5) 0.5631(3) 0.0511(13) Uani 1 1 d . . . . .
H11 H 0.143364 0.352309 0.537092 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1593(4) 0.5871(5) 0.5024(3) 0.0413(11) Uani 1 1 d . . . . .
C13 C 0.1578(5) 0.4241(6) 0.3589(4) 0.0689(16) Uani 1 1 d . . . . .
H13A H 0.216703 0.355033 0.389210 0.103 Uiso 1 1 calc R U . . .
H13B H 0.165593 0.436181 0.289126 0.103 Uiso 1 1 calc R U . . .
H13C H 0.086130 0.375720 0.366706 0.103 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 1.443(3) . ?
S1 N1 1.547(4) . ?
S1 C6 1.762(5) . ?
S1 C7 1.765(4) . ?
F1 C2 1.349(5) . ?
F2 C3 1.353(5) . ?
F3 C4 1.338(5) . ?
F4 C5 1.342(5) . ?
O2 C12 1.354(5) . ?
O2 C13 1.431(5) . ?
N1 C1 1.376(6) . ?
N2 C3 1.296(6) . ?
N2 C4 1.309(6) . ?
C1 C5 1.383(7) . ?
C1 C2 1.403(6) . ?
C2 C3 1.363(7) . ?
C4 C5 1.369(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.384(5) . ?
C7 C12 1.399(6) . ?
C8 C9 1.377(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(5) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N1 120.7(2) . . ?
O1 S1 C6 108.0(2) . . ?
N1 S1 C6 102.6(2) . . ?
O1 S1 C7 107.36(19) . . ?
N1 S1 C7 110.7(2) . . ?
C6 S1 C7 106.6(2) . . ?
C12 O2 C13 118.9(3) . . ?
C1 N1 S1 122.8(3) . . ?
C3 N2 C4 115.8(5) . . ?
N1 C1 C5 128.8(4) . . ?
N1 C1 C2 118.0(4) . . ?
C5 C1 C2 113.1(5) . . ?
F1 C2 C3 119.8(4) . . ?
F1 C2 C1 119.2(5) . . ?
C3 C2 C1 120.9(4) . . ?
N2 C3 F2 116.9(5) . . ?
N2 C3 C2 124.6(5) . . ?
F2 C3 C2 118.4(5) . . ?
N2 C4 F3 116.8(6) . . ?
N2 C4 C5 124.5(5) . . ?
F3 C4 C5 118.7(5) . . ?
F4 C5 C4 119.8(5) . . ?
F4 C5 C1 119.2(5) . . ?
C4 C5 C1 121.0(4) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 120.1(4) . . ?
C8 C7 S1 118.4(3) . . ?
C12 C7 S1 121.4(3) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O2 C12 C11 125.0(4) . . ?
O2 C12 C7 115.6(3) . . ?
C11 C12 C7 119.4(4) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_3n
_database_code_depnum_ccdc_archive 'CCDC 2027290'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3n
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 F4 N3 O S'
_chemical_formula_sum            'C11 H7 F4 N3 O S'
_chemical_formula_weight         305.26

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.0531(5)
_cell_length_b                   8.2642(3)
_cell_length_c                   14.0691(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.556(4)
_cell_angle_gamma                90
_cell_volume                     1158.72(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4011
_cell_measurement_theta_min      2.6570
_cell_measurement_theta_max      29.0910

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7025
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2089
_reflns_number_gt                1793
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0415P)²+0.7462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2089
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.70561(5) 0.58865(6) 0.49916(3) 0.01829(16) Uani 1 1 d . . . . .
F1 F 0.59029(12) 0.38872(13) 0.75173(8) 0.0244(3) Uani 1 1 d . . . . .
F2 F 0.53476(13) 0.55907(15) 0.90461(8) 0.0285(3) Uani 1 1 d . . . . .
F3 F 0.57912(13) 1.03494(14) 0.75502(8) 0.0286(3) Uani 1 1 d . . . . .
F4 F 0.65139(13) 0.89139(14) 0.60043(8) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.63226(15) 0.69682(16) 0.43069(9) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.64976(17) 0.5359(2) 0.59121(11) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.55731(17) 0.7974(2) 0.83029(11) 0.0220(4) Uani 1 1 d . . . . .
N3 N 0.78631(18) 0.4088(2) 0.36682(11) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.62256(19) 0.6301(2) 0.66654(13) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.59050(19) 0.5516(2) 0.74849(14) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.5616(2) 0.6383(3) 0.82575(13) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.5855(2) 0.8724(2) 0.75376(14) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.6201(2) 0.7990(2) 0.67335(13) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.7239(2) 0.3954(2) 0.44453(13) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.8009(2) 0.2715(3) 0.31908(14) 0.0269(5) Uani 1 1 d . . . . .
H7 H 0.845961 0.275677 0.263885 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7535(2) 0.1235(3) 0.34607(14) 0.0249(5) Uani 1 1 d . . . . .
H8 H 0.765513 0.028952 0.309756 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6885(2) 0.1152(2) 0.42653(14) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.654186 0.014991 0.445825 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6740(2) 0.2548(2) 0.47876(14) 0.0212(4) Uani 1 1 d . . . . .
H10 H 0.631783 0.253576 0.535331 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8725(2) 0.6594(3) 0.52374(14) 0.0234(5) Uani 1 1 d . . . . .
H11A H 0.911823 0.667266 0.463750 0.035 Uiso 1 1 calc R U . . .
H11B H 0.925292 0.583777 0.567204 0.035 Uiso 1 1 calc R U . . .
H11C H 0.872994 0.766307 0.553897 0.035 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 1.4436(14) . ?
S1 N1 1.5406(16) . ?
S1 C11 1.768(2) . ?
S1 C6 1.7920(19) . ?
F1 C2 1.346(2) . ?
F2 C3 1.346(2) . ?
F3 C4 1.345(2) . ?
F4 C5 1.349(2) . ?
N1 C1 1.371(2) . ?
N2 C4 1.305(3) . ?
N2 C3 1.318(3) . ?
N3 C6 1.335(2) . ?
N3 C7 1.337(3) . ?
C1 C2 1.397(3) . ?
C1 C5 1.400(3) . ?
C2 C3 1.365(3) . ?
C4 C5 1.368(3) . ?
C6 C10 1.377(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 N1 121.70(9) . . ?
O1 S1 C11 108.31(10) . . ?
N1 S1 C11 111.75(9) . . ?
O1 S1 C6 109.74(8) . . ?
N1 S1 C6 100.24(9) . . ?
C11 S1 C6 103.33(10) . . ?
C1 N1 S1 128.39(15) . . ?
C4 N2 C3 114.95(17) . . ?
C6 N3 C7 115.80(17) . . ?
N1 C1 C2 117.74(18) . . ?
N1 C1 C5 128.76(18) . . ?
C2 C1 C5 113.49(17) . . ?
F1 C2 C3 119.76(17) . . ?
F1 C2 C1 119.58(17) . . ?
C3 C2 C1 120.65(19) . . ?
N2 C3 F2 115.73(17) . . ?
N2 C3 C2 125.06(18) . . ?
F2 C3 C2 119.21(18) . . ?
N2 C4 F3 116.58(17) . . ?
N2 C4 C5 125.32(19) . . ?
F3 C4 C5 118.10(17) . . ?
F4 C5 C4 119.24(17) . . ?
F4 C5 C1 120.29(17) . . ?
C4 C5 C1 120.47(18) . . ?
N3 C6 C10 126.04(18) . . ?
N3 C6 S1 111.28(14) . . ?
C10 C6 S1 122.64(15) . . ?
N3 C7 C8 123.26(19) . . ?
N3 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C9 C8 C7 119.09(19) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.14(19) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C6 C10 C9 116.66(18) . . ?
C6 C10 H10 121.7 . . ?
C9 C10 H10 121.7 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_3m
_database_code_depnum_ccdc_archive 'CCDC 2027289'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3m
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 F4 N3 O3 S'
_chemical_formula_sum            'C12 H7 F4 N3 O3 S'
_chemical_formula_weight         349.27

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'
S S 0.1246 0.1234 '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'

_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                   7.8496(4)
_cell_length_b                   11.5105(5)
_cell_length_c                   14.9480(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.919(2)
_cell_angle_gamma                90
_cell_volume                     1326.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2894
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8081
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         28.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3445
_reflns_number_gt                1941
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0428P)²+1.1804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3445
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.83784(11) 0.87377(7) 0.56411(6) 0.0245(2) Uani 1 1 d . . . . .
F1 F 1.2322(3) 0.67792(18) 0.48341(15) 0.0441(6) Uani 1 1 d . . . . .
F2 F 1.1765(3) 0.50443(19) 0.36120(15) 0.0559(7) Uani 1 1 d . . . . .
F3 F 0.5984(3) 0.5145(2) 0.34788(16) 0.0578(7) Uani 1 1 d . . . . .
F4 F 0.6235(3) 0.68666(18) 0.46854(15) 0.0444(6) Uani 1 1 d . . . . .
O1 O 0.7394(3) 0.9365(2) 0.48772(15) 0.0313(6) Uani 1 1 d . . . . .
O2 O 0.1950(3) 0.7401(2) 0.77654(18) 0.0387(6) Uani 1 1 d . . . . .
O3 O 0.3896(3) 0.6190(2) 0.84430(17) 0.0424(7) Uani 1 1 d . . . . .
N1 N 0.9699(4) 0.7813(2) 0.54647(19) 0.0279(7) Uani 1 1 d . . . . .
N2 N 0.8874(5) 0.5086(3) 0.3540(2) 0.0442(9) Uani 1 1 d . . . . .
N3 N 0.3404(4) 0.6961(2) 0.7891(2) 0.0307(7) Uani 1 1 d . . . . .
C1 C 0.9310(5) 0.6932(3) 0.4827(2) 0.0279(8) Uani 1 1 d . . . . .
C2 C 1.0696(5) 0.6412(3) 0.4515(2) 0.0327(8) Uani 1 1 d . . . . .
C3 C 1.0407(6) 0.5524(3) 0.3898(2) 0.0370(9) Uani 1 1 d . . . . .
C4 C 0.7574(6) 0.5565(3) 0.3829(2) 0.0404(10) Uani 1 1 d . . . . .
C5 C 0.7691(5) 0.6456(3) 0.4451(2) 0.0329(8) Uani 1 1 d . . . . .
C6 C 0.6898(4) 0.8198(3) 0.6315(2) 0.0223(7) Uani 1 1 d . . . . .
C7 C 0.5180(4) 0.8528(3) 0.6089(2) 0.0275(7) Uani 1 1 d . . . . .
H7 H 0.479455 0.902824 0.558641 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4031(4) 0.8115(3) 0.6610(2) 0.0297(8) Uani 1 1 d . . . . .
H8 H 0.284087 0.832722 0.647210 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4643(4) 0.7393(3) 0.7331(2) 0.0240(7) Uani 1 1 d . . . . .
C10 C 0.6342(4) 0.7036(3) 0.7557(2) 0.0264(7) Uani 1 1 d . . . . .
H10 H 0.670795 0.652264 0.805359 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7513(4) 0.7447(3) 0.7038(2) 0.0245(7) Uani 1 1 d . . . . .
H11 H 0.869842 0.722280 0.717258 0.029 Uiso 1 1 calc R U . . .
C12 C 0.9697(4) 0.9690(3) 0.6376(2) 0.0278(8) Uani 1 1 d . . . . .
H12A H 1.055713 1.003767 0.605970 0.042 Uiso 1 1 calc R U . . .
H12B H 1.029231 0.926312 0.691188 0.042 Uiso 1 1 calc R U . . .
H12C H 0.898045 1.030469 0.656844 0.042 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 1.445(2) . ?
S1 N1 1.543(3) . ?
S1 C12 1.746(3) . ?
S1 C6 1.788(3) . ?
F1 C2 1.343(4) . ?
F2 C3 1.340(4) . ?
F3 C4 1.348(4) . ?
F4 C5 1.343(4) . ?
O2 N3 1.230(4) . ?
O3 N3 1.224(4) . ?
N1 C1 1.386(4) . ?
N2 C4 1.304(5) . ?
N2 C3 1.320(5) . ?
N3 C9 1.484(4) . ?
C1 C2 1.397(5) . ?
C1 C5 1.400(5) . ?
C2 C3 1.367(5) . ?
C4 C5 1.376(5) . ?
C6 C7 1.380(4) . ?
C6 C11 1.396(4) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(5) . ?
C10 C11 1.392(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 119.07(15) . . ?
O1 S1 C12 110.34(15) . . ?
N1 S1 C12 101.74(16) . . ?
O1 S1 C6 108.16(15) . . ?
N1 S1 C6 112.71(15) . . ?
C12 S1 C6 103.57(15) . . ?
C1 N1 S1 123.7(2) . . ?
C4 N2 C3 114.5(3) . . ?
O3 N3 O2 124.5(3) . . ?
O3 N3 C9 117.8(3) . . ?
O2 N3 C9 117.7(3) . . ?
N1 C1 C2 117.3(3) . . ?
N1 C1 C5 128.9(3) . . ?
C2 C1 C5 113.8(3) . . ?
F1 C2 C3 120.0(3) . . ?
F1 C2 C1 119.7(3) . . ?
C3 C2 C1 120.3(4) . . ?
N2 C3 F2 115.6(3) . . ?
N2 C3 C2 125.5(4) . . ?
F2 C3 C2 118.9(4) . . ?
N2 C4 F3 116.4(4) . . ?
N2 C4 C5 125.7(4) . . ?
F3 C4 C5 117.9(4) . . ?
F4 C5 C4 119.2(4) . . ?
F4 C5 C1 120.7(3) . . ?
C4 C5 C1 120.1(4) . . ?
C7 C6 C11 122.5(3) . . ?
C7 C6 S1 118.4(2) . . ?
C11 C6 S1 119.0(2) . . ?
C6 C7 C8 118.6(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 123.5(3) . . ?
C8 C9 N3 118.4(3) . . ?
C10 C9 N3 118.0(3) . . ?
C9 C10 C11 118.2(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C6 118.3(3) . . ?
C10 C11 H11 120.9 . . ?
C6 C11 H11 120.9 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.081



####################################################################### 
# 
# 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_3k
_database_code_depnum_ccdc_archive 'CCDC 2027287'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3k
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F4 N2 O2 S'
_chemical_formula_sum            'C13 H10 F4 N2 O2 S'
_chemical_formula_weight         334.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.3261(7)
_cell_length_b                   5.2819(2)
_cell_length_c                   19.7479(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.245(4)
_cell_angle_gamma                90
_cell_volume                     1363.31(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1321
_cell_measurement_theta_min      3.2250
_cell_measurement_theta_max      27.6290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4062
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         25.750
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2563
_reflns_number_gt                2117
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0336P)²+0.7714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2563
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
S1 S 0.48300(4) 0.35504(11) 0.39380(3) 0.01722(16) Uani 1 1 d . . . . .
F1 F 0.63150(11) 0.6013(3) 0.32245(7) 0.0311(4) Uani 1 1 d . . . . .
F2 F 0.81488(12) 0.5957(3) 0.28815(8) 0.0423(4) Uani 1 1 d . . . . .
F3 F 0.91617(11) -0.0885(3) 0.41950(8) 0.0439(4) Uani 1 1 d . . . . .
F4 F 0.73594(11) -0.1207(3) 0.45995(7) 0.0320(4) Uani 1 1 d . . . . .
O1 O 0.47454(12) 0.6251(3) 0.40399(8) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.33017(14) 0.1853(4) 0.09761(8) 0.0364(5) Uani 1 1 d . . . . .
N1 N 0.58464(14) 0.2139(4) 0.41945(9) 0.0189(4) Uani 1 1 d . . . . .
N2 N 0.86627(15) 0.2545(4) 0.35401(11) 0.0302(5) Uani 1 1 d . . . . .
C1 C 0.67326(17) 0.2403(4) 0.39438(10) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.69906(18) 0.4217(4) 0.34939(11) 0.0211(5) Uani 1 1 d . . . . .
C3 C 0.79357(19) 0.4189(5) 0.33202(12) 0.0269(6) Uani 1 1 d . . . . .
C4 C 0.84305(19) 0.0821(5) 0.39609(13) 0.0282(6) Uani 1 1 d . . . . .
C5 C 0.75117(18) 0.0657(5) 0.41700(11) 0.0227(5) Uani 1 1 d . . . . .
C6 C 0.40052(17) 0.1978(5) 0.43877(11) 0.0208(5) Uani 1 1 d . . . . .
H6A H 0.425821 0.216626 0.488546 0.031 Uiso 1 1 calc R U . . .
H6B H 0.397743 0.017735 0.426610 0.031 Uiso 1 1 calc R U . . .
H6C H 0.331832 0.271138 0.426329 0.031 Uiso 1 1 calc R U . . .
C7 C 0.43583(16) 0.2917(4) 0.30546(10) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.47166(17) 0.0853(4) 0.27437(11) 0.0197(5) Uani 1 1 d . . . . .
H8 H 0.519336 -0.027508 0.300863 0.024 Uiso 1 1 calc R U . . .
C9 C 0.43768(17) 0.0434(5) 0.20421(11) 0.0219(5) Uani 1 1 d . . . . .
H9 H 0.462221 -0.097360 0.182262 0.026 Uiso 1 1 calc R U . . .
C10 C 0.36778(18) 0.2085(5) 0.16668(11) 0.0240(5) Uani 1 1 d . . . . .
C11 C 0.33005(18) 0.4122(5) 0.19881(12) 0.0261(6) Uani 1 1 d . . . . .
H11 H 0.280114 0.520866 0.172831 0.031 Uiso 1 1 calc R U . . .
C12 C 0.36475(17) 0.4566(5) 0.26799(12) 0.0224(5) Uani 1 1 d . . . . .
H12 H 0.340500 0.597980 0.289854 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3767(2) -0.0001(6) 0.06087(12) 0.0387(7) Uani 1 1 d . . . . .
H13A H 0.450349 0.032799 0.067450 0.058 Uiso 1 1 calc R U . . .
H13B H 0.346226 0.009044 0.011586 0.058 Uiso 1 1 calc R U . . .
H13C H 0.365432 -0.169201 0.078399 0.058 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 1.4479(17) . ?
S1 N1 1.5426(19) . ?
S1 C6 1.751(2) . ?
S1 C7 1.767(2) . ?
F1 C2 1.344(3) . ?
F2 C3 1.341(3) . ?
F3 C4 1.341(3) . ?
F4 C5 1.340(3) . ?
O2 C10 1.364(3) . ?
O2 C13 1.430(3) . ?
N1 C1 1.374(3) . ?
N2 C4 1.310(3) . ?
N2 C3 1.311(3) . ?
C1 C2 1.394(3) . ?
C1 C5 1.395(3) . ?
C2 C3 1.368(3) . ?
C4 C5 1.369(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.381(3) . ?
C7 C12 1.389(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C11 C12 1.374(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N1 121.18(11) . . ?
O1 S1 C6 108.85(11) . . ?
N1 S1 C6 101.66(11) . . ?
O1 S1 C7 107.53(10) . . ?
N1 S1 C7 110.68(10) . . ?
C6 S1 C7 105.86(10) . . ?
C10 O2 C13 117.2(2) . . ?
C1 N1 S1 126.45(16) . . ?
C4 N2 C3 114.8(2) . . ?
N1 C1 C2 129.5(2) . . ?
N1 C1 C5 117.1(2) . . ?
C2 C1 C5 113.4(2) . . ?
F1 C2 C3 119.1(2) . . ?
F1 C2 C1 120.5(2) . . ?
C3 C2 C1 120.4(2) . . ?
N2 C3 F2 116.1(2) . . ?
N2 C3 C2 125.5(2) . . ?
F2 C3 C2 118.4(2) . . ?
N2 C4 F3 116.1(2) . . ?
N2 C4 C5 124.8(2) . . ?
F3 C4 C5 119.1(2) . . ?
F4 C5 C4 119.5(2) . . ?
F4 C5 C1 119.5(2) . . ?
C4 C5 C1 121.0(2) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 121.1(2) . . ?
C8 C7 S1 120.06(17) . . ?
C12 C7 S1 118.78(17) . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O2 C10 C9 123.9(2) . . ?
O2 C10 C11 115.5(2) . . ?
C9 C10 C11 120.6(2) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_3r
_database_code_depnum_ccdc_archive 'CCDC 2027293'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3r
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 F4 N2 O S2'
_chemical_formula_sum            'C10 H6 F4 N2 O S2'
_chemical_formula_weight         310.29

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'
S S 0.1246 0.1234 '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'

_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                   11.1807(6)
_cell_length_b                   8.2524(5)
_cell_length_c                   13.2410(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.781(3)
_cell_angle_gamma                90
_cell_volume                     1181.29(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2493
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.495
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8328
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         25.195
_diffrn_reflns_theta_full        25.195
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2129
_reflns_number_gt                1133
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0215P)²+2.7369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2129
_refine_ls_number_parameters     186
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.054
_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
S2A S 0.7589(3) 0.9722(5) 0.5130(4) 0.0517(12) Uani 0.608(6) 1 d D . P A 1
C7A C 0.8437(5) 0.7998(6) 0.5409(4) 0.0317(15) Uani 0.608(6) 1 d D . P A 1
C8A C 0.9537(14) 0.825(2) 0.6098(14) 0.0453(18) Uani 0.608(6) 1 d D . P A 1
H8A H 1.011402 0.739237 0.631655 0.054 Uiso 0.608(6) 1 calc R U P A 1
C9A C 0.979(3) 0.9865(17) 0.6487(19) 0.046(3) Uani 0.608(6) 1 d D . P A 1
H9A H 1.050210 1.025491 0.698635 0.056 Uiso 0.608(6) 1 calc R U P A 1
C10A C 0.878(2) 1.070(2) 0.5971(16) 0.046(3) Uani 0.608(6) 1 d D . P A 1
H10A H 0.873133 1.183612 0.607761 0.055 Uiso 0.608(6) 1 calc R U P A 1
S2B S 0.9863(5) 0.7998(8) 0.6275(6) 0.0453(18) Uani 0.392(6) 1 d D . P A 2
C7B C 0.8437(5) 0.7998(6) 0.5409(4) 0.0317(15) Uani 0.392(6) 1 d D . P A 2
C8B C 0.792(2) 0.951(2) 0.522(2) 0.0517(12) Uani 0.392(6) 1 d D . P A 2
H8B H 0.712197 0.965979 0.475926 0.062 Uiso 0.392(6) 1 calc R U P A 2
C9B C 0.862(3) 1.088(4) 0.575(3) 0.046(3) Uani 0.392(6) 1 d D . P A 2
H9B H 0.842585 1.200440 0.572055 0.055 Uiso 0.392(6) 1 calc R U P A 2
C10B C 0.965(4) 1.008(2) 0.631(3) 0.046(3) Uani 0.392(6) 1 d D . P A 2
H10B H 1.029021 1.070632 0.674330 0.056 Uiso 0.392(6) 1 calc R U P A 2
S1 S 0.78740(13) 0.61528(18) 0.48596(12) 0.0343(4) Uani 1 1 d D . . . .
F1 F 0.4376(3) 0.8058(5) 0.3642(3) 0.0609(12) Uani 1 1 d . . . . .
F2 F 0.2395(3) 0.6474(6) 0.2507(3) 0.0758(14) Uani 1 1 d . . . . .
F3 F 0.4310(4) 0.1638(5) 0.3195(3) 0.0692(13) Uani 1 1 d . . . . .
F4 F 0.6443(3) 0.3011(4) 0.4247(3) 0.0579(11) Uani 1 1 d . . . . .
O1 O 0.8459(4) 0.4873(5) 0.5558(3) 0.0449(12) Uani 1 1 d . . . . .
N1 N 0.6477(4) 0.6509(6) 0.4603(4) 0.0371(13) Uani 1 1 d . . . . .
N2 N 0.3358(5) 0.4045(9) 0.2834(4) 0.0560(17) Uani 1 1 d . . . . .
C1 C 0.5513(5) 0.5610(8) 0.3995(4) 0.0331(15) Uani 1 1 d . . . . .
C2 C 0.4427(6) 0.6444(9) 0.3543(5) 0.0413(17) Uani 1 1 d . . . . .
C3 C 0.3413(6) 0.5628(10) 0.2982(5) 0.0461(18) Uani 1 1 d . . . . .
C4 C 0.4357(7) 0.3245(9) 0.3282(5) 0.0465(18) Uani 1 1 d . . . . .
C5 C 0.5444(6) 0.3946(8) 0.3840(5) 0.0428(17) Uani 1 1 d . . . . .
C6 C 0.8356(5) 0.5946(8) 0.3696(5) 0.0438(17) Uani 1 1 d . . . . .
H6A H 0.925833 0.583995 0.386676 0.066 Uiso 1 1 calc R U . . .
H6B H 0.810282 0.690520 0.325739 0.066 Uiso 1 1 calc R U . . .
H6C H 0.797423 0.497864 0.331913 0.066 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
S2A C7A 1.697(6) . ?
S2A C10A 1.706(12) . ?
C7A C8A 1.347(14) . ?
C7A S1 1.735(5) . ?
C8A C9A 1.433(16) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.354(13) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
S2B C7B 1.709(7) . ?
S2B C10B 1.738(17) . ?
C7B C8B 1.375(17) . ?
C7B S1 1.735(5) . ?
C8B C9B 1.451(19) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.366(17) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
S1 O1 1.446(4) . ?
S1 N1 1.540(5) . ?
S1 C6 1.765(6) . ?
F1 C2 1.342(7) . ?
F2 C3 1.347(7) . ?
F3 C4 1.331(7) . ?
F4 C5 1.352(7) . ?
N1 C1 1.385(7) . ?
N2 C4 1.303(8) . ?
N2 C3 1.320(8) . ?
C1 C5 1.387(8) . ?
C1 C2 1.391(8) . ?
C2 C3 1.364(9) . ?
C4 C5 1.379(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C7A S2A C10A 87.5(8) . . ?
C8A C7A S2A 112.4(9) . . ?
C8A C7A S1 126.1(9) . . ?
S2A C7A S1 121.4(3) . . ?
C7A C8A C9A 116.7(16) . . ?
C7A C8A H8A 121.6 . . ?
C9A C8A H8A 121.6 . . ?
C10A C9A C8A 103(2) . . ?
C10A C9A H9A 128.4 . . ?
C8A C9A H9A 128.4 . . ?
C9A C10A S2A 120.0(18) . . ?
C9A C10A H10A 120.0 . . ?
S2A C10A H10A 120.0 . . ?
C7B S2B C10B 84.6(14) . . ?
C8B C7B S2B 113.6(13) . . ?
C8B C7B S1 129.1(13) . . ?
S2B C7B S1 117.3(4) . . ?
C7B C8B C9B 118(3) . . ?
C7B C8B H8B 121.0 . . ?
C9B C8B H8B 121.0 . . ?
C10B C9B C8B 99(3) . . ?
C10B C9B H9B 130.4 . . ?
C8B C9B H9B 130.4 . . ?
C9B C10B S2B 125(3) . . ?
C9B C10B H10B 117.7 . . ?
S2B C10B H10B 117.7 . . ?
O1 S1 N1 123.3(3) . . ?
O1 S1 C7B 108.4(3) . . ?
N1 S1 C7B 99.5(3) . . ?
O1 S1 C7A 108.4(3) . . ?
N1 S1 C7A 99.5(3) . . ?
O1 S1 C6 107.4(3) . . ?
N1 S1 C6 110.1(3) . . ?
C7B S1 C6 106.9(3) . . ?
C7A S1 C6 106.9(3) . . ?
C1 N1 S1 128.4(4) . . ?
C4 N2 C3 115.6(6) . . ?
N1 C1 C5 128.5(5) . . ?
N1 C1 C2 116.7(6) . . ?
C5 C1 C2 114.6(6) . . ?
F1 C2 C3 119.6(6) . . ?
F1 C2 C1 120.2(6) . . ?
C3 C2 C1 120.2(7) . . ?
N2 C3 F2 116.2(6) . . ?
N2 C3 C2 124.8(6) . . ?
F2 C3 C2 119.0(7) . . ?
N2 C4 F3 117.1(6) . . ?
N2 C4 C5 124.6(7) . . ?
F3 C4 C5 118.3(7) . . ?
F4 C5 C4 120.0(6) . . ?
F4 C5 C1 119.8(5) . . ?
C4 C5 C1 120.2(6) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_3v
_database_code_depnum_ccdc_archive 'CCDC 2027295'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3v
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 F4 N2 O S'
_chemical_formula_sum            'C18 H12 F4 N2 O S'
_chemical_formula_weight         380.36

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   17.4257(16)
_cell_length_b                   16.0239(14)
_cell_length_c                   5.7231(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1598.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2185
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6245
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9247
_diffrn_reflns_av_unetI/netI     0.1272
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         25.191
_diffrn_reflns_theta_full        25.191
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2842
_reflns_number_gt                1762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.976

_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0166P)²+1.0686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
S1 S 0.75395(13) 0.64269(11) 0.4014(3) 0.0284(5) Uani 1 1 d . . . . .
F1 F 0.6137(3) 0.5812(3) 0.1463(7) 0.0465(13) Uani 1 1 d . . . . .
F2 F 0.4640(3) 0.5464(3) 0.1724(9) 0.0545(15) Uani 1 1 d . . . . .
F3 F 0.4379(3) 0.6872(3) 0.8495(7) 0.0490(14) Uani 1 1 d . . . . .
F4 F 0.5875(3) 0.7304(3) 0.8548(7) 0.0431(13) Uani 1 1 d . . . . .
O1 O 0.7715(3) 0.6513(3) 0.1548(7) 0.0355(14) Uani 1 1 d . . . . .
N1 N 0.6843(4) 0.6864(4) 0.5094(10) 0.0304(17) Uani 1 1 d . . . . .
N2 N 0.4495(4) 0.6170(4) 0.5109(12) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.6097(5) 0.6587(5) 0.5006(13) 0.028(2) Uani 1 1 d . . . . .
C2 C 0.5729(5) 0.6113(5) 0.3264(10) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.4963(5) 0.5926(5) 0.3431(12) 0.037(2) Uani 1 1 d . . . . .
C4 C 0.4842(5) 0.6620(5) 0.6724(14) 0.037(2) Uani 1 1 d . . . . .
C5 C 0.5592(5) 0.6840(4) 0.6780(14) 0.031(2) Uani 1 1 d . . . . .
C6 C 0.8291(5) 0.6892(5) 0.5708(11) 0.033(2) Uani 1 1 d . . . . .
H6A H 0.828844 0.750237 0.543723 0.039 Uiso 1 1 calc R U . . .
H6B H 0.818466 0.679619 0.738547 0.039 Uiso 1 1 calc R U . . .
C7 C 0.9079(5) 0.6555(5) 0.5140(13) 0.0272(19) Uani 1 1 d . . . . .
C8 C 0.9437(5) 0.6033(5) 0.6720(13) 0.0321(19) Uani 1 1 d . . . . .
H8 H 0.917866 0.586426 0.810355 0.039 Uiso 1 1 calc R U . . .
C9 C 1.0180(5) 0.5755(5) 0.6269(14) 0.038(2) Uani 1 1 d . . . . .
H9 H 1.043016 0.539813 0.735232 0.046 Uiso 1 1 calc R U . . .
C10 C 1.0553(5) 0.5998(5) 0.4247(14) 0.043(2) Uani 1 1 d . . . . .
H10 H 1.106284 0.581339 0.395768 0.052 Uiso 1 1 calc R U . . .
C11 C 1.0189(5) 0.6507(5) 0.2648(14) 0.040(2) Uani 1 1 d . . . . .
H11 H 1.044473 0.666714 0.125227 0.048 Uiso 1 1 calc R U . . .
C12 C 0.9457(5) 0.6781(5) 0.3077(12) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.920511 0.712575 0.196681 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7550(5) 0.5352(4) 0.4690(10) 0.0251(19) Uani 1 1 d . . . . .
C14 C 0.7253(5) 0.5064(5) 0.6800(12) 0.036(2) Uani 1 1 d . . . . .
H14 H 0.705295 0.544677 0.791313 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7250(5) 0.4225(5) 0.7255(13) 0.041(2) Uani 1 1 d . . . . .
H15 H 0.703703 0.402289 0.867491 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7556(5) 0.3671(5) 0.5661(13) 0.039(2) Uani 1 1 d . . . . .
H16 H 0.756787 0.309112 0.600266 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7843(5) 0.3961(5) 0.3578(13) 0.038(2) Uani 1 1 d . . . . .
H17 H 0.803905 0.357643 0.246380 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7851(4) 0.4797(5) 0.3087(12) 0.031(2) Uani 1 1 d . . . . .
H18 H 0.806106 0.499395 0.165783 0.038 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 1.451(5) . ?
S1 N1 1.531(7) . ?
S1 C13 1.765(6) . ?
S1 C6 1.792(8) . ?
F1 C2 1.342(8) . ?
F2 C3 1.350(8) . ?
F3 C4 1.358(9) . ?
F4 C5 1.349(8) . ?
N1 C1 1.374(10) . ?
N2 C4 1.318(10) . ?
N2 C3 1.319(9) . ?
C1 C5 1.403(11) . ?
C1 C2 1.408(10) . ?
C2 C3 1.371(11) . ?
C4 C5 1.354(10) . ?
C6 C7 1.511(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.381(10) . ?
C7 C12 1.399(10) . ?
C8 C9 1.392(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.381(9) . ?
C13 C14 1.393(9) . ?
C14 C15 1.371(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.369(10) . ?
C17 H17 0.9500 . ?
C18 H18 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 N1 121.1(3) . . ?
O1 S1 C13 107.7(3) . . ?
N1 S1 C13 111.5(4) . . ?
O1 S1 C6 109.5(3) . . ?
N1 S1 C6 99.8(3) . . ?
C13 S1 C6 106.2(4) . . ?
C1 N1 S1 125.9(6) . . ?
C4 N2 C3 112.9(8) . . ?
N1 C1 C5 118.2(7) . . ?
N1 C1 C2 129.1(7) . . ?
C5 C1 C2 112.5(7) . . ?
F1 C2 C3 119.4(7) . . ?
F1 C2 C1 119.8(8) . . ?
C3 C2 C1 120.8(7) . . ?
N2 C3 F2 115.6(8) . . ?
N2 C3 C2 126.0(7) . . ?
F2 C3 C2 118.4(7) . . ?
N2 C4 C5 127.0(8) . . ?
N2 C4 F3 114.4(8) . . ?
C5 C4 F3 118.6(7) . . ?
F4 C5 C4 120.9(7) . . ?
F4 C5 C1 118.2(8) . . ?
C4 C5 C1 120.8(8) . . ?
C7 C6 S1 113.5(5) . . ?
C7 C6 H6A 108.9 . . ?
S1 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
S1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C12 119.7(8) . . ?
C8 C7 C6 119.1(7) . . ?
C12 C7 C6 121.2(7) . . ?
C7 C8 C9 119.5(7) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.2(7) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.2(8) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.9(8) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 120.4(8) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 120.3(6) . . ?
C18 C13 S1 119.1(5) . . ?
C14 C13 S1 120.6(5) . . ?
C15 C14 C13 119.4(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.3(7) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.8(7) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.4(7) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_3p
_database_code_depnum_ccdc_archive 'CCDC 2027292'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3p
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 F4 N3 O S'
_chemical_formula_sum            'C11 H7 F4 N3 O S'
_chemical_formula_weight         305.26

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

_cell_length_a                   8.5581(3)
_cell_length_b                   11.2534(5)
_cell_length_c                   25.1484(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2421.99(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1525
_cell_measurement_theta_min      2.8650
_cell_measurement_theta_max      28.8190

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5470
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.879
_diffrn_reflns_theta_max         26.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2553
_reflns_number_gt                1996
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0386P)²+0.7134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2553
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.75338(7) 0.62763(4) 0.60709(2) 0.01738(16) Uani 1 1 d . . . . .
F1 F 0.53086(16) 0.79145(10) 0.65343(5) 0.0271(3) Uani 1 1 d . . . . .
F2 F 0.41414(16) 0.89737(10) 0.73989(5) 0.0285(3) Uani 1 1 d . . . . .
F3 F 0.69605(18) 0.66692(12) 0.85109(5) 0.0313(3) Uani 1 1 d . . . . .
F4 F 0.83597(15) 0.55311(10) 0.76980(5) 0.0216(3) Uani 1 1 d . . . . .
O1 O 0.78562(19) 0.74348(12) 0.58445(6) 0.0252(4) Uani 1 1 d . . . . .
N1 N 0.7704(2) 0.60444(14) 0.66730(7) 0.0180(4) Uani 1 1 d . . . . .
N2 N 0.5564(2) 0.78324(15) 0.79574(7) 0.0219(4) Uani 1 1 d . . . . .
N3 N 0.2747(2) 0.50791(17) 0.54707(7) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.6928(3) 0.66696(17) 0.70674(8) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.5826(3) 0.75756(17) 0.70193(8) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.5212(3) 0.81134(17) 0.74649(9) 0.0202(5) Uani 1 1 d . . . . .
C4 C 0.6591(3) 0.69706(18) 0.80074(8) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.7298(3) 0.63810(16) 0.75957(9) 0.0168(5) Uani 1 1 d . . . . .
C6 C 0.8810(3) 0.52273(18) 0.57930(8) 0.0223(5) Uani 1 1 d . . . . .
H6A H 0.876302 0.527754 0.540425 0.033 Uiso 1 1 calc R U . . .
H6B H 0.850110 0.442823 0.590681 0.033 Uiso 1 1 calc R U . . .
H6C H 0.987862 0.538985 0.591248 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5652(3) 0.58143(17) 0.58414(8) 0.0160(4) Uani 1 1 d . . . . .
C8 C 0.4951(3) 0.48187(17) 0.60569(8) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.544136 0.437696 0.633215 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3498(3) 0.44863(19) 0.58560(9) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.301116 0.379973 0.600046 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3453(3) 0.60461(19) 0.52752(8) 0.0240(5) Uani 1 1 d . . . . .
H10 H 0.293173 0.648004 0.500396 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4897(3) 0.64522(18) 0.54449(8) 0.0219(5) Uani 1 1 d . . . . .
H11 H 0.535599 0.714413 0.529501 0.026 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 1.4491(15) . ?
S1 N1 1.5434(17) . ?
S1 C6 1.754(2) . ?
S1 C7 1.788(2) . ?
F1 C2 1.353(2) . ?
F2 C3 1.343(2) . ?
F3 C4 1.348(2) . ?
F4 C5 1.344(2) . ?
N1 C1 1.386(3) . ?
N2 C3 1.313(3) . ?
N2 C4 1.315(3) . ?
N3 C10 1.338(3) . ?
N3 C9 1.340(3) . ?
C1 C2 1.394(3) . ?
C1 C5 1.404(3) . ?
C2 C3 1.378(3) . ?
C4 C5 1.370(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.382(3) . ?
C7 C11 1.388(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 H11 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 N1 121.31(9) . . ?
O1 S1 C6 109.29(10) . . ?
N1 S1 C6 102.61(10) . . ?
O1 S1 C7 107.84(9) . . ?
N1 S1 C7 110.66(10) . . ?
C6 S1 C7 103.67(10) . . ?
C1 N1 S1 124.82(15) . . ?
C3 N2 C4 114.91(18) . . ?
C10 N3 C9 117.0(2) . . ?
N1 C1 C2 129.31(19) . . ?
N1 C1 C5 116.85(18) . . ?
C2 C1 C5 113.83(18) . . ?
F1 C2 C3 119.00(19) . . ?
F1 C2 C1 120.39(18) . . ?
C3 C2 C1 120.58(19) . . ?
N2 C3 F2 116.52(19) . . ?
N2 C3 C2 125.0(2) . . ?
F2 C3 C2 118.5(2) . . ?
N2 C4 F3 115.59(18) . . ?
N2 C4 C5 125.5(2) . . ?
F3 C4 C5 119.0(2) . . ?
F4 C5 C4 119.90(19) . . ?
F4 C5 C1 119.89(18) . . ?
C4 C5 C1 120.21(19) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C11 119.9(2) . . ?
C8 C7 S1 120.03(16) . . ?
C11 C7 S1 120.05(16) . . ?
C7 C8 C9 117.6(2) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
N3 C9 C8 123.8(2) . . ?
N3 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
N3 C10 C11 123.9(2) . . ?
N3 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C10 C11 C7 117.8(2) . . ?
C10 C11 H11 121.1 . . ?
C7 C11 H11 121.1 . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_3u
_database_code_depnum_ccdc_archive 'CCDC 2027294'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_3k                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5666  
RESPONSE: The crystals supplied were 
weakly diffracting, even with prolonged 
exposure times, which made it difficult 
to observe the high angle reflections. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3u
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 F4 N2 O S'
_chemical_formula_sum            'C17 H10 F4 N2 O S'
_chemical_formula_weight         366.33

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'
S S 0.1246 0.1234 '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'

_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                   14.0056(7)
_cell_length_b                   9.7724(6)
_cell_length_c                   11.3208(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.263(4)
_cell_angle_gamma                90
_cell_volume                     1542.93(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3492
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9996
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         23.749
_diffrn_reflns_theta_full        23.749
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2348
_reflns_number_gt                1438
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0434P)²+4.9177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2348
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
S1 S 0.69164(11) 0.35973(17) 0.60866(13) 0.0304(4) Uani 1 1 d . . . . .
F1 F 0.8790(2) 0.4987(4) 0.6228(3) 0.0423(10) Uani 1 1 d . . . . .
F2 F 0.9967(3) 0.6742(4) 0.5284(3) 0.0519(11) Uani 1 1 d . . . . .
F3 F 0.7844(3) 0.7555(4) 0.2112(3) 0.0570(12) Uani 1 1 d . . . . .
F4 F 0.6540(2) 0.5869(4) 0.2927(3) 0.0454(10) Uani 1 1 d . . . . .
O1 O 0.7033(3) 0.4192(4) 0.7264(3) 0.0369(11) Uani 1 1 d . . . . .
N1 N 0.6873(3) 0.4510(5) 0.4974(4) 0.0347(13) Uani 1 1 d . . . . .
N2 N 0.8916(4) 0.7156(6) 0.3701(5) 0.0428(14) Uani 1 1 d . . . . .
C1 C 0.7597(4) 0.5339(6) 0.4626(5) 0.0311(15) Uani 1 1 d . . . . .
C2 C 0.8493(4) 0.5605(7) 0.5184(5) 0.0318(16) Uani 1 1 d . . . . .
C3 C 0.9104(4) 0.6485(7) 0.4701(6) 0.0384(16) Uani 1 1 d . . . . .
C4 C 0.8062(5) 0.6906(7) 0.3151(5) 0.0403(17) Uani 1 1 d . . . . .
C5 C 0.7398(4) 0.6062(6) 0.3557(5) 0.0334(16) Uani 1 1 d . . . . .
C6 C 0.5796(4) 0.2749(6) 0.5880(5) 0.0303(15) Uani 1 1 d . . . . .
C7 C 0.5146(5) 0.2999(8) 0.4909(6) 0.0457(19) Uani 1 1 d . . . . .
H7 H 0.527537 0.365476 0.432506 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4304(5) 0.2260(8) 0.4820(6) 0.050(2) Uani 1 1 d . . . . .
H8 H 0.384347 0.241916 0.416529 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4113(5) 0.1292(8) 0.5661(7) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.353509 0.077708 0.557280 0.065 Uiso 1 1 calc R U . . .
C10 C 0.4770(5) 0.1083(8) 0.6627(7) 0.060(2) Uani 1 1 d . . . . .
H10 H 0.463228 0.044279 0.721905 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5613(5) 0.1784(7) 0.6742(6) 0.0482(19) Uani 1 1 d . . . . .
H11 H 0.607017 0.161936 0.739948 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7765(4) 0.2269(6) 0.6009(5) 0.0295(15) Uani 1 1 d . . . . .
C13 C 0.8403(4) 0.1969(7) 0.6992(5) 0.0380(17) Uani 1 1 d . . . . .
H13 H 0.840132 0.249231 0.769914 0.046 Uiso 1 1 calc R U . . .
C14 C 0.9042(5) 0.0888(7) 0.6920(6) 0.0436(18) Uani 1 1 d . . . . .
H14 H 0.948461 0.066848 0.757908 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9029(5) 0.0137(8) 0.5885(6) 0.0458(18) Uani 1 1 d . . . . .
H15 H 0.946120 -0.060714 0.583939 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8402(5) 0.0451(7) 0.4923(6) 0.0443(18) Uani 1 1 d . . . . .
H16 H 0.840573 -0.007090 0.421546 0.053 Uiso 1 1 calc R U . . .
C17 C 0.7771(4) 0.1514(7) 0.4975(5) 0.0375(16) Uani 1 1 d . . . . .
H17 H 0.733851 0.173212 0.430485 0.045 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 1.450(4) . ?
S1 N1 1.540(5) . ?
S1 C12 1.768(6) . ?
S1 C6 1.772(6) . ?
F1 C2 1.358(6) . ?
F2 C3 1.347(7) . ?
F3 C4 1.346(7) . ?
F4 C5 1.352(6) . ?
N1 C1 1.383(7) . ?
N2 C3 1.314(8) . ?
N2 C4 1.320(8) . ?
C1 C2 1.377(8) . ?
C1 C5 1.406(8) . ?
C2 C3 1.363(8) . ?
C4 C5 1.355(9) . ?
C6 C7 1.383(8) . ?
C6 C11 1.398(8) . ?
C7 C8 1.378(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.361(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.384(8) . ?
C12 C13 1.393(8) . ?
C13 C14 1.392(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.369(9) . ?
C16 H16 0.9500 . ?
C17 H17 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 N1 120.8(3) . . ?
O1 S1 C12 108.7(3) . . ?
N1 S1 C12 111.1(3) . . ?
O1 S1 C6 109.5(3) . . ?
N1 S1 C6 101.2(3) . . ?
C12 S1 C6 104.0(3) . . ?
C1 N1 S1 126.7(4) . . ?
C3 N2 C4 114.5(6) . . ?
C2 C1 N1 129.8(5) . . ?
C2 C1 C5 113.6(6) . . ?
N1 C1 C5 116.5(5) . . ?
F1 C2 C3 118.4(5) . . ?
F1 C2 C1 120.6(6) . . ?
C3 C2 C1 121.0(6) . . ?
N2 C3 F2 115.4(6) . . ?
N2 C3 C2 125.2(6) . . ?
F2 C3 C2 119.3(6) . . ?
N2 C4 F3 116.6(6) . . ?
N2 C4 C5 125.0(6) . . ?
F3 C4 C5 118.4(6) . . ?
F4 C5 C4 120.6(5) . . ?
F4 C5 C1 118.7(5) . . ?
C4 C5 C1 120.7(6) . . ?
C7 C6 C11 121.7(6) . . ?
C7 C6 S1 122.2(5) . . ?
C11 C6 S1 116.1(5) . . ?
C8 C7 C6 117.5(7) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C9 121.7(7) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 119.2(7) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.8(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 119.0(7) . . ?
C10 C11 H11 120.5 . . ?
C6 C11 H11 120.5 . . ?
C17 C12 C13 120.7(6) . . ?
C17 C12 S1 119.3(5) . . ?
C13 C12 S1 120.0(5) . . ?
C14 C13 C12 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 119.7(6) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.8(7) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.4(7) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 119.6(6) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_3w
_database_code_depnum_ccdc_archive 'CCDC 2027296'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3w
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F4 N2 O S'
_chemical_formula_sum            'C13 H10 F4 N2 O S'
_chemical_formula_weight         318.29

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'
S S 0.1246 0.1234 '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'

_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                   5.5360(3)
_cell_length_b                   14.1989(11)
_cell_length_c                   17.2077(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.051(4)
_cell_angle_gamma                90
_cell_volume                     1352.39(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3416
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.131

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9865
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         29.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3621
_reflns_number_gt                1986
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0011P)²+3.2059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3621
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1621
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 0.38145(16) 0.65169(8) 0.54669(6) 0.0250(2) Uani 1 1 d . . . . .
F1 F -0.0862(4) 0.7346(2) 0.36540(15) 0.0419(7) Uani 1 1 d . . . . .
F2 F -0.0606(5) 0.8980(2) 0.28731(16) 0.0591(9) Uani 1 1 d . . . . .
F3 F 0.6168(5) 0.9860(2) 0.41799(17) 0.0545(8) Uani 1 1 d . . . . .
F4 F 0.6330(4) 0.8254(2) 0.49927(15) 0.0421(7) Uani 1 1 d . . . . .
O1 O 0.6363(4) 0.6292(2) 0.54972(16) 0.0322(7) Uani 1 1 d . . . . .
N1 N 0.2545(6) 0.6822(3) 0.46970(19) 0.0285(8) Uani 1 1 d . . . . .
N2 N 0.2790(7) 0.9420(3) 0.3522(2) 0.0405(10) Uani 1 1 d . . . . .
C1 C 0.2757(7) 0.7701(3) 0.4365(2) 0.0283(9) Uani 1 1 d . . . . .
C2 C 0.0963(7) 0.7942(3) 0.3804(2) 0.0309(10) Uani 1 1 d . . . . .
C3 C 0.1106(8) 0.8785(4) 0.3419(2) 0.0366(11) Uani 1 1 d . . . . .
C4 C 0.4446(8) 0.9209(4) 0.4055(3) 0.0363(11) Uani 1 1 d . . . . .
C5 C 0.4516(7) 0.8387(3) 0.4469(2) 0.0322(10) Uani 1 1 d . . . . .
C6 C 0.3214(6) 0.7340(3) 0.6214(2) 0.0225(8) Uani 1 1 d . . . . .
C7 C 0.4874(7) 0.7433(3) 0.6821(2) 0.0304(10) Uani 1 1 d . . . . .
H7 H 0.629045 0.705488 0.684178 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4426(8) 0.8087(4) 0.7396(3) 0.0382(11) Uani 1 1 d . . . . .
H8 H 0.554401 0.816349 0.781703 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2355(8) 0.8629(3) 0.7360(3) 0.0363(11) Uani 1 1 d . . . . .
H9 H 0.206958 0.908378 0.775301 0.044 Uiso 1 1 calc R U . . .
C10 C 0.0689(7) 0.8515(3) 0.6757(3) 0.0333(10) Uani 1 1 d . . . . .
H10 H -0.073454 0.888849 0.673716 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1104(7) 0.7855(3) 0.6182(2) 0.0273(9) Uani 1 1 d . . . . .
H11 H -0.004482 0.775895 0.577234 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2125(7) 0.5491(3) 0.5693(2) 0.0303(10) Uani 1 1 d . . . . .
H12A H 0.043518 0.567358 0.579643 0.036 Uiso 1 1 calc R U . . .
H12B H 0.210599 0.506363 0.523803 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3156(8) 0.4973(3) 0.6391(3) 0.0415(12) Uani 1 1 d . . . . .
H13A H 0.481282 0.477426 0.628525 0.062 Uiso 1 1 calc R U . . .
H13B H 0.216206 0.441772 0.649622 0.062 Uiso 1 1 calc R U . . .
H13C H 0.316027 0.539082 0.684430 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 1.446(3) . ?
S1 N1 1.550(3) . ?
S1 C6 1.773(4) . ?
S1 C12 1.778(4) . ?
F1 C2 1.340(5) . ?
F2 C3 1.350(5) . ?
F3 C4 1.342(5) . ?
F4 C5 1.350(4) . ?
N1 C1 1.379(5) . ?
N2 C3 1.307(6) . ?
N2 C4 1.319(6) . ?
C1 C5 1.386(6) . ?
C1 C2 1.414(6) . ?
C2 C3 1.371(6) . ?
C4 C5 1.368(6) . ?
C6 C11 1.378(5) . ?
C6 C7 1.385(5) . ?
C7 C8 1.384(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.512(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N1 121.26(18) . . ?
O1 S1 C6 108.35(17) . . ?
N1 S1 C6 110.34(19) . . ?
O1 S1 C12 109.17(18) . . ?
N1 S1 C12 100.56(19) . . ?
C6 S1 C12 105.98(19) . . ?
C1 N1 S1 124.5(3) . . ?
C3 N2 C4 115.0(4) . . ?
N1 C1 C5 130.4(4) . . ?
N1 C1 C2 116.0(4) . . ?
C5 C1 C2 113.6(4) . . ?
F1 C2 C3 120.5(4) . . ?
F1 C2 C1 119.8(4) . . ?
C3 C2 C1 119.7(4) . . ?
N2 C3 F2 116.3(4) . . ?
N2 C3 C2 125.7(4) . . ?
F2 C3 C2 118.0(4) . . ?
N2 C4 F3 115.9(4) . . ?
N2 C4 C5 124.7(4) . . ?
F3 C4 C5 119.4(4) . . ?
F4 C5 C4 118.7(4) . . ?
F4 C5 C1 120.0(4) . . ?
C4 C5 C1 121.3(4) . . ?
C11 C6 C7 122.0(4) . . ?
C11 C6 S1 119.4(3) . . ?
C7 C6 S1 118.6(3) . . ?
C8 C7 C6 118.6(4) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C6 C11 C10 118.8(4) . . ?
C6 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 S1 112.3(3) . . ?
C13 C12 H12A 109.1 . . ?
S1 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
S1 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.092



####################################################################### 
# 
# 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_3s
_database_code_depnum_ccdc_archive 'CCDC 2027298'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3s
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 F4 N2 O S'
_chemical_formula_sum            'C7 H6 F4 N2 O S'
_chemical_formula_weight         242.20

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'
S S 0.1246 0.1234 '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'

_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                   9.2463(4)
_cell_length_b                   10.7616(6)
_cell_length_c                   9.3227(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.151(2)
_cell_angle_gamma                90
_cell_volume                     891.04(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1794
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5203
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         29.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2403
_reflns_number_gt                1995
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0311P)²+0.8490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2403
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.73371(5) 0.41925(4) 0.38727(5) 0.02042(13) Uani 1 1 d . . . . .
F1 F 0.45021(14) 0.54904(12) 0.22963(17) 0.0367(3) Uani 1 1 d . . . . .
F2 F 0.15099(15) 0.53712(13) 0.11842(18) 0.0428(4) Uani 1 1 d . . . . .
F3 F 0.12320(14) 0.17470(12) 0.35195(16) 0.0342(3) Uani 1 1 d . . . . .
F4 F 0.42086(14) 0.16918(11) 0.47788(15) 0.0300(3) Uani 1 1 d . . . . .
O1 O 0.75667(16) 0.55104(13) 0.41284(17) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.60584(18) 0.35062(16) 0.4321(2) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.13638(19) 0.35496(17) 0.2334(2) 0.0270(4) Uani 1 1 d . . . . .
C1 C 0.4539(2) 0.35769(18) 0.3596(2) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.3760(2) 0.45156(18) 0.2649(2) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.2219(2) 0.4447(2) 0.2077(2) 0.0268(4) Uani 1 1 d . . . . .
C4 C 0.2088(2) 0.26683(19) 0.3221(2) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.3609(2) 0.26312(18) 0.3861(2) 0.0211(4) Uani 1 1 d . . . . .
C6 C 0.8926(2) 0.3405(2) 0.4955(3) 0.0295(5) Uani 1 1 d . . . . .
H6A H 0.983120 0.373592 0.474046 0.044 Uiso 1 1 calc R U . . .
H6B H 0.883284 0.251692 0.471414 0.044 Uiso 1 1 calc R U . . .
H6C H 0.900322 0.352145 0.601644 0.044 Uiso 1 1 calc R U . . .
C7 C 0.7306(2) 0.3877(2) 0.2006(2) 0.0302(5) Uani 1 1 d . . . . .
H7A H 0.656056 0.441301 0.133321 0.045 Uiso 1 1 calc R U . . .
H7B H 0.703596 0.300424 0.177591 0.045 Uiso 1 1 calc R U . . .
H7C H 0.830326 0.403832 0.187208 0.045 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 1.4440(15) . ?
S1 N1 1.5468(17) . ?
S1 C6 1.752(2) . ?
S1 C7 1.766(2) . ?
F1 C2 1.343(2) . ?
F2 C3 1.344(2) . ?
F3 C4 1.345(2) . ?
F4 C5 1.341(2) . ?
N1 C1 1.381(2) . ?
N2 C3 1.312(3) . ?
N2 C4 1.313(3) . ?
C1 C5 1.398(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.377(3) . ?
C4 C5 1.367(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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 N1 120.85(9) . . ?
O1 S1 C6 108.59(10) . . ?
N1 S1 C6 101.25(10) . . ?
O1 S1 C7 108.24(10) . . ?
N1 S1 C7 111.72(10) . . ?
C6 S1 C7 104.83(11) . . ?
C1 N1 S1 126.27(15) . . ?
C3 N2 C4 114.79(18) . . ?
N1 C1 C5 117.77(17) . . ?
N1 C1 C2 128.49(18) . . ?
C5 C1 C2 113.68(18) . . ?
F1 C2 C3 119.40(18) . . ?
F1 C2 C1 120.57(18) . . ?
C3 C2 C1 120.03(18) . . ?
N2 C3 F2 116.26(18) . . ?
N2 C3 C2 125.44(19) . . ?
F2 C3 C2 118.30(19) . . ?
N2 C4 F3 115.88(17) . . ?
N2 C4 C5 125.33(19) . . ?
F3 C4 C5 118.78(18) . . ?
F4 C5 C4 119.56(17) . . ?
F4 C5 C1 119.70(17) . . ?
C4 C5 C1 120.72(18) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.069



####################################################################### 
# 
# 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_3y
_database_code_depnum_ccdc_archive 'CCDC 2027297'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3y
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F4 N2 O S'
_chemical_formula_sum            'C14 H10 F4 N2 O S'
_chemical_formula_weight         330.30

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'
S S 0.1246 0.1234 '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'

_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                   5.6040(2)
_cell_length_b                   14.6697(10)
_cell_length_c                   17.1224(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.862(3)
_cell_angle_gamma                90
_cell_volume                     1402.55(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3079
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.131

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6442
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_full        25.193
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2525
_reflns_number_gt                1437
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0516P)²+1.6050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.6430(2) 0.66270(9) 0.43148(8) 0.0233(4) Uani 1 1 d . . . . .
F1 F 1.1079(5) 0.7374(2) 0.62553(19) 0.0441(10) Uani 1 1 d . . . . .
F2 F 1.0778(6) 0.8912(3) 0.7088(2) 0.0568(11) Uani 1 1 d . . . . .
F3 F 0.3836(6) 0.9718(2) 0.5751(2) 0.0579(11) Uani 1 1 d . . . . .
F4 F 0.3793(5) 0.8225(2) 0.48516(19) 0.0480(10) Uani 1 1 d . . . . .
O1 O 0.3927(5) 0.6375(2) 0.4230(2) 0.0287(9) Uani 1 1 d . . . . .
N1 N 0.7694(7) 0.6886(3) 0.5124(3) 0.0276(11) Uani 1 1 d . . . . .
N2 N 0.7314(8) 0.9312(4) 0.6428(3) 0.0395(13) Uani 1 1 d . . . . .
C1 C 0.7413(8) 0.7703(4) 0.5500(3) 0.0250(13) Uani 1 1 d . . . . .
C2 C 0.9189(9) 0.7937(4) 0.6099(3) 0.0287(13) Uani 1 1 d . . . . .
C3 C 0.9029(10) 0.8715(4) 0.6523(3) 0.0356(15) Uani 1 1 d . . . . .
C4 C 0.5637(10) 0.9114(4) 0.5870(4) 0.0362(15) Uani 1 1 d . . . . .
C5 C 0.5607(9) 0.8347(4) 0.5400(3) 0.0302(14) Uani 1 1 d . . . . .
C6 C 0.6915(8) 0.7479(4) 0.3611(3) 0.0232(13) Uani 1 1 d . . . . .
C7 C 0.9000(9) 0.7980(4) 0.3686(3) 0.0313(14) Uani 1 1 d . . . . .
H7 H 1.015392 0.788401 0.411716 0.038 Uiso 1 1 calc R U . . .
C8 C 0.9380(9) 0.8621(4) 0.3127(4) 0.0359(15) Uani 1 1 d . . . . .
H8 H 1.078598 0.898533 0.318061 0.043 Uiso 1 1 calc R U . . .
C9 C 0.7738(9) 0.8742(4) 0.2485(4) 0.0375(16) Uani 1 1 d . . . . .
H9 H 0.803044 0.917807 0.209358 0.045 Uiso 1 1 calc R U . . .
C10 C 0.5683(10) 0.8228(4) 0.2417(4) 0.0393(16) Uani 1 1 d . . . . .
H10 H 0.455403 0.831469 0.197743 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5226(9) 0.7590(4) 0.2972(3) 0.0291(14) Uani 1 1 d . . . . .
H11 H 0.380304 0.723542 0.292238 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8142(9) 0.5709(4) 0.4049(3) 0.0261(13) Uani 1 1 d . . . . .
H12 H 0.992165 0.578407 0.411565 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7177(11) 0.4760(4) 0.4153(3) 0.0357(15) Uani 1 1 d . . . . .
H13A H 0.834348 0.426685 0.428913 0.043 Uiso 1 1 calc R U . . .
H13B H 0.563142 0.469952 0.438837 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7142(10) 0.5164(4) 0.3360(3) 0.0310(14) Uani 1 1 d . . . . .
H14A H 0.557225 0.535147 0.310051 0.037 Uiso 1 1 calc R U . . .
H14B H 0.828265 0.491906 0.300133 0.037 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 1.446(3) . ?
S1 N1 1.549(4) . ?
S1 C12 1.737(5) . ?
S1 C6 1.772(5) . ?
F1 C2 1.351(6) . ?
F2 C3 1.349(6) . ?
F3 C4 1.346(6) . ?
F4 C5 1.336(6) . ?
N1 C1 1.375(7) . ?
N2 C3 1.301(7) . ?
N2 C4 1.315(7) . ?
C1 C5 1.385(7) . ?
C1 C2 1.410(7) . ?
C2 C3 1.359(8) . ?
C4 C5 1.382(8) . ?
C6 C7 1.378(7) . ?
C6 C11 1.394(7) . ?
C7 C8 1.371(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.495(7) . ?
C12 C13 1.509(7) . ?
C12 H12 1.0000 . ?
C13 C14 1.480(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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 N1 121.2(2) . . ?
O1 S1 C12 109.2(2) . . ?
N1 S1 C12 101.7(2) . . ?
O1 S1 C6 108.4(2) . . ?
N1 S1 C6 110.5(2) . . ?
C12 S1 C6 104.4(2) . . ?
C1 N1 S1 124.8(4) . . ?
C3 N2 C4 114.6(5) . . ?
N1 C1 C5 130.4(5) . . ?
N1 C1 C2 116.8(5) . . ?
C5 C1 C2 112.8(5) . . ?
F1 C2 C3 119.6(5) . . ?
F1 C2 C1 119.2(5) . . ?
C3 C2 C1 121.2(5) . . ?
N2 C3 F2 115.4(5) . . ?
N2 C3 C2 125.5(5) . . ?
F2 C3 C2 119.1(5) . . ?
N2 C4 F3 116.4(5) . . ?
N2 C4 C5 125.2(5) . . ?
F3 C4 C5 118.4(5) . . ?
F4 C5 C4 119.3(5) . . ?
F4 C5 C1 120.0(5) . . ?
C4 C5 C1 120.7(5) . . ?
C7 C6 C11 121.6(5) . . ?
C7 C6 S1 119.4(4) . . ?
C11 C6 S1 118.9(4) . . ?
C8 C7 C6 118.8(5) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 120.7(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 118.0(5) . . ?
C10 C11 H11 121.0 . . ?
C6 C11 H11 121.0 . . ?
C14 C12 C13 59.0(3) . . ?
C14 C12 S1 116.3(4) . . ?
C13 C12 S1 118.2(4) . . ?
C14 C12 H12 116.9 . . ?
C13 C12 H12 116.9 . . ?
S1 C12 H12 116.9 . . ?
C14 C13 C12 60.0(4) . . ?
C14 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C14 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C13 C14 C12 60.9(4) . . ?
C13 C14 H14A 117.7 . . ?
C12 C14 H14A 117.7 . . ?
C13 C14 H14B 117.7 . . ?
C12 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_3q
_database_code_depnum_ccdc_archive 'CCDC 2027300'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3q
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 F4 N3 O2 S'
_chemical_formula_sum            'C11 H7 F4 N3 O2 S'
_chemical_formula_weight         321.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.3052(4)
_cell_length_b                   7.6862(4)
_cell_length_c                   11.7607(7)
_cell_angle_alpha                103.097(4)
_cell_angle_beta                 91.929(4)
_cell_angle_gamma                106.247(5)
_cell_volume                     614.16(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3386
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.323
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5280
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2477
_reflns_number_gt                1748
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0241P)²+0.7302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
S1 S 0.41589(12) 0.58228(12) -0.23509(7) 0.0366(2) Uani 1 1 d . . . . .
F1 F 0.1622(3) 0.4853(3) -0.57503(17) 0.0560(6) Uani 1 1 d . . . . .
F2 F 0.0364(4) 0.1497(4) -0.7286(2) 0.0741(8) Uani 1 1 d . . . . .
F3 F 0.2873(4) -0.1251(3) -0.4882(2) 0.0775(8) Uani 1 1 d . . . . .
F4 F 0.4241(3) 0.1930(3) -0.32501(19) 0.0616(7) Uani 1 1 d . . . . .
O1 O 0.5930(3) 0.5657(4) -0.1872(2) 0.0506(7) Uani 1 1 d . . . . .
O2 O -0.2056(4) 0.1273(4) -0.0359(2) 0.0607(8) Uani 1 1 d . . . . .
N1 N 0.3600(4) 0.5352(4) -0.3682(2) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.1635(5) 0.0121(5) -0.6089(3) 0.0558(9) Uani 1 1 d . . . . .
N3 N -0.0667(4) 0.2323(4) -0.0780(2) 0.0405(7) Uani 1 1 d . . . . .
C1 C 0.2988(5) 0.3579(5) -0.4408(3) 0.0349(7) Uani 1 1 d . . . . .
C2 C 0.1965(5) 0.3362(5) -0.5483(3) 0.0398(8) Uani 1 1 d . . . . .
C3 C 0.1354(5) 0.1657(6) -0.6257(3) 0.0478(9) Uani 1 1 d . . . . .
C4 C 0.2573(6) 0.0297(5) -0.5087(4) 0.0519(10) Uani 1 1 d . . . . .
C5 C 0.3269(5) 0.1933(5) -0.4241(3) 0.0420(8) Uani 1 1 d . . . . .
C6 C 0.4166(5) 0.8165(5) -0.1924(3) 0.0480(9) Uani 1 1 d . . . . .
H6A H 0.436941 0.859388 -0.106664 0.072 Uiso 1 1 calc R U . . .
H6B H 0.293231 0.827238 -0.220337 0.072 Uiso 1 1 calc R U . . .
H6C H 0.519958 0.893683 -0.226530 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2270(5) 0.4526(4) -0.1692(3) 0.0335(7) Uani 1 1 d . . . . .
C8 C 0.0389(5) 0.4480(5) -0.1937(3) 0.0400(8) Uani 1 1 d . . . . .
H8 H 0.009913 0.521638 -0.242596 0.048 Uiso 1 1 calc R U . . .
C9 C -0.1047(5) 0.3384(5) -0.1479(3) 0.0422(8) Uani 1 1 d . . . . .
H9 H -0.233355 0.336365 -0.165140 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1161(5) 0.2351(5) -0.0532(3) 0.0434(9) Uani 1 1 d . . . . .
H10 H 0.142012 0.159943 -0.004491 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2646(5) 0.3443(5) -0.0971(3) 0.0414(8) Uani 1 1 d . . . . .
H11 H 0.392644 0.345942 -0.078240 0.050 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 1.444(2) . ?
S1 N1 1.538(3) . ?
S1 C6 1.754(4) . ?
S1 C7 1.775(3) . ?
F1 C2 1.339(4) . ?
F2 C3 1.351(4) . ?
F3 C4 1.339(4) . ?
F4 C5 1.345(4) . ?
O2 N3 1.297(4) . ?
N1 C1 1.376(4) . ?
N2 C4 1.303(5) . ?
N2 C3 1.310(5) . ?
N3 C10 1.350(4) . ?
N3 C9 1.354(4) . ?
C1 C5 1.391(5) . ?
C1 C2 1.399(4) . ?
C2 C3 1.360(5) . ?
C4 C5 1.368(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.383(4) . ?
C7 C11 1.385(4) . ?
C8 C9 1.359(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.369(5) . ?
C10 H10 0.9500 . ?
C11 H11 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 N1 121.81(16) . . ?
O1 S1 C6 109.12(17) . . ?
N1 S1 C6 101.68(16) . . ?
O1 S1 C7 107.46(14) . . ?
N1 S1 C7 109.11(15) . . ?
C6 S1 C7 106.73(17) . . ?
C1 N1 S1 125.3(2) . . ?
C4 N2 C3 115.3(3) . . ?
O2 N3 C10 120.2(3) . . ?
O2 N3 C9 120.1(3) . . ?
C10 N3 C9 119.7(3) . . ?
N1 C1 C5 129.2(3) . . ?
N1 C1 C2 116.9(3) . . ?
C5 C1 C2 113.9(3) . . ?
F1 C2 C3 120.4(3) . . ?
F1 C2 C1 119.4(3) . . ?
C3 C2 C1 120.2(3) . . ?
N2 C3 F2 116.2(3) . . ?
N2 C3 C2 125.2(3) . . ?
F2 C3 C2 118.6(3) . . ?
N2 C4 F3 116.9(4) . . ?
N2 C4 C5 124.9(4) . . ?
F3 C4 C5 118.2(4) . . ?
F4 C5 C4 119.0(3) . . ?
F4 C5 C1 120.5(3) . . ?
C4 C5 C1 120.4(3) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C11 118.5(3) . . ?
C8 C7 S1 121.3(2) . . ?
C11 C7 S1 120.1(2) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
N3 C9 C8 120.9(3) . . ?
N3 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N3 C10 C11 121.2(3) . . ?
N3 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C7 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C7 C11 H11 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
O1 S1 N1 C1 73.5(3) . . . . ?
C6 S1 N1 C1 -165.1(3) . . . . ?
C7 S1 N1 C1 -52.6(3) . . . . ?
S1 N1 C1 C5 -21.7(5) . . . . ?
S1 N1 C1 C2 159.6(3) . . . . ?
N1 C1 C2 F1 -0.4(5) . . . . ?
C5 C1 C2 F1 -179.3(3) . . . . ?
N1 C1 C2 C3 178.5(3) . . . . ?
C5 C1 C2 C3 -0.4(5) . . . . ?
C4 N2 C3 F2 -179.2(3) . . . . ?
C4 N2 C3 C2 0.4(6) . . . . ?
F1 C2 C3 N2 179.1(3) . . . . ?
C1 C2 C3 N2 0.2(6) . . . . ?
F1 C2 C3 F2 -1.3(5) . . . . ?
C1 C2 C3 F2 179.8(3) . . . . ?
C3 N2 C4 F3 179.5(3) . . . . ?
C3 N2 C4 C5 -0.7(6) . . . . ?
N2 C4 C5 F4 -179.0(4) . . . . ?
F3 C4 C5 F4 0.8(5) . . . . ?
N2 C4 C5 C1 0.6(6) . . . . ?
F3 C4 C5 C1 -179.7(3) . . . . ?
N1 C1 C5 F4 0.9(6) . . . . ?
C2 C1 C5 F4 179.6(3) . . . . ?
N1 C1 C5 C4 -178.6(3) . . . . ?
C2 C1 C5 C4 0.1(5) . . . . ?
O1 S1 C7 C8 177.2(3) . . . . ?
N1 S1 C7 C8 -48.9(3) . . . . ?
C6 S1 C7 C8 60.3(3) . . . . ?
O1 S1 C7 C11 -6.6(3) . . . . ?
N1 S1 C7 C11 127.3(3) . . . . ?
C6 S1 C7 C11 -123.6(3) . . . . ?
C11 C7 C8 C9 -0.3(5) . . . . ?
S1 C7 C8 C9 175.9(3) . . . . ?
O2 N3 C9 C8 -179.4(3) . . . . ?
C10 N3 C9 C8 0.1(5) . . . . ?
C7 C8 C9 N3 -0.1(5) . . . . ?
O2 N3 C10 C11 179.8(3) . . . . ?
C9 N3 C10 C11 0.3(5) . . . . ?
N3 C10 C11 C7 -0.7(5) . . . . ?
C8 C7 C11 C10 0.7(5) . . . . ?
S1 C7 C11 C10 -175.6(3) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2027299'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H6 F12 N4 O S'
_chemical_formula_sum            'C22 H6 F12 N4 O S'
_chemical_formula_weight         602.37

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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   40.6740(18)
_cell_length_b                   32.9096(15)
_cell_length_c                   6.3175(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8456.4(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4101
_cell_measurement_theta_min      2.0070
_cell_measurement_theta_max      26.7670

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_F_000             4768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12983
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3737
_reflns_number_gt                3091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.946

_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0013P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     361
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S1 S 0.64718(3) 0.42024(3) 0.42538(18) 0.0167(3) Uani 1 1 d . . . . .
F1 F 0.57920(5) 0.43568(7) 0.2006(4) 0.0265(6) Uani 1 1 d . . . . .
F2 F 0.51574(6) 0.45103(7) 0.3042(5) 0.0358(7) Uani 1 1 d . . . . .
F3 F 0.52557(6) 0.38828(8) 0.9373(4) 0.0346(7) Uani 1 1 d . . . . .
F4 F 0.58970(6) 0.37044(7) 0.8667(4) 0.0288(6) Uani 1 1 d . . . . .
F5 F 0.65854(5) 0.35096(7) 0.1261(4) 0.0242(6) Uani 1 1 d . . . . .
F6 F 0.66932(6) 0.27227(7) 0.0633(4) 0.0305(7) Uani 1 1 d . . . . .
F7 F 0.71506(6) 0.25559(7) 0.7099(4) 0.0319(7) Uani 1 1 d . . . . .
F8 F 0.70887(5) 0.33546(7) 0.8000(4) 0.0225(6) Uani 1 1 d . . . . .
F9 F 0.71591(5) 0.44778(7) 0.8043(4) 0.0246(6) Uani 1 1 d . . . . .
F10 F 0.77383(6) 0.48349(7) 0.7044(4) 0.0314(7) Uani 1 1 d . . . . .
F11 F 0.77584(6) 0.42410(7) 0.0583(4) 0.0315(7) Uani 1 1 d . . . . .
F12 F 0.71834(6) 0.38677(7) 0.1238(4) 0.0237(6) Uani 1 1 d . . . . .
O1 O 0.65325(6) 0.43189(8) 0.2077(5) 0.0218(7) Uani 1 1 d . . . . .
N1 N 0.61997(8) 0.39083(9) 0.4948(6) 0.0186(8) Uani 1 1 d . . . . .
N2 N 0.52079(8) 0.41961(10) 0.6201(7) 0.0259(10) Uani 1 1 d . . . . .
N3 N 0.69240(8) 0.26416(10) 0.3863(6) 0.0219(9) Uani 1 1 d . . . . .
N4 N 0.77455(8) 0.45388(10) 0.3821(6) 0.0224(9) Uani 1 1 d . . . . .
C1 C 0.58730(10) 0.40221(11) 0.5293(7) 0.0180(10) Uani 1 1 d . . . . .
C2 C 0.56717(10) 0.42296(12) 0.3892(7) 0.0207(11) Uani 1 1 d . . . . .
C3 C 0.53487(11) 0.43080(12) 0.4413(8) 0.0247(11) Uani 1 1 d . . . . .
C4 C 0.53987(11) 0.40009(13) 0.7533(7) 0.0237(11) Uani 1 1 d . . . . .
C5 C 0.57220(10) 0.39068(12) 0.7175(7) 0.0217(11) Uani 1 1 d . . . . .
C6 C 0.68302(9) 0.39277(11) 0.5257(7) 0.0152(10) Uani 1 1 d . . . . .
H6 H 0.681417 0.393836 0.683591 0.018 Uiso 1 1 calc R U . . .
C7 C 0.68386(9) 0.34760(12) 0.4671(7) 0.0158(10) Uani 1 1 d . . . . .
C8 C 0.67384(10) 0.32984(12) 0.2806(7) 0.0192(10) Uani 1 1 d . . . . .
C9 C 0.67905(10) 0.28855(13) 0.2483(8) 0.0248(11) Uani 1 1 d . . . . .
C10 C 0.70164(10) 0.28047(12) 0.5654(8) 0.0214(11) Uani 1 1 d . . . . .
C11 C 0.69802(10) 0.32124(12) 0.6137(7) 0.0183(10) Uani 1 1 d . . . . .
C12 C 0.71436(9) 0.41532(12) 0.4680(7) 0.0153(10) Uani 1 1 d . . . . .
C13 C 0.72952(10) 0.44117(12) 0.6123(7) 0.0182(10) Uani 1 1 d . . . . .
C14 C 0.75909(10) 0.45909(12) 0.5604(8) 0.0210(10) Uani 1 1 d . . . . .
C15 C 0.76018(10) 0.43009(13) 0.2421(7) 0.0212(11) Uani 1 1 d . . . . .
C16 C 0.73051(10) 0.41076(12) 0.2767(7) 0.0183(10) Uani 1 1 d . . . . .
C17 C 0.64577(9) 0.46551(11) 0.5779(7) 0.0149(10) Uani 1 1 d . . . . .
C18 C 0.65506(9) 0.50176(12) 0.4799(7) 0.0198(10) Uani 1 1 d . . . . .
H18 H 0.663397 0.501889 0.339459 0.024 Uiso 1 1 calc R U . . .
C19 C 0.65176(10) 0.53764(13) 0.5940(8) 0.0246(11) Uani 1 1 d . . . . .
H19 H 0.657692 0.562805 0.530935 0.030 Uiso 1 1 calc R U . . .
C20 C 0.63976(10) 0.53680(13) 0.8007(8) 0.0261(11) Uani 1 1 d . . . . .
H20 H 0.637453 0.561485 0.877283 0.031 Uiso 1 1 calc R U . . .
C21 C 0.63115(9) 0.50032(12) 0.8960(7) 0.0217(10) Uani 1 1 d . . . . .
H21 H 0.623285 0.500053 1.037554 0.026 Uiso 1 1 calc R U . . .
C22 C 0.63405(9) 0.46416(11) 0.7836(7) 0.0170(10) Uani 1 1 d . . . . .
H22 H 0.628114 0.439008 0.846783 0.020 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 1.449(3) . ?
S1 N1 1.534(3) . ?
S1 C17 1.775(4) . ?
S1 C6 1.828(4) . ?
F1 C2 1.354(5) . ?
F2 C3 1.341(5) . ?
F3 C4 1.357(5) . ?
F4 C5 1.356(5) . ?
F5 C8 1.350(4) . ?
F6 C9 1.345(5) . ?
F7 C10 1.342(5) . ?
F8 C11 1.342(4) . ?
F9 C13 1.351(5) . ?
F10 C14 1.353(5) . ?
F11 C15 1.339(5) . ?
F12 C16 1.342(5) . ?
N1 C1 1.398(5) . ?
N2 C4 1.313(6) . ?
N2 C3 1.319(6) . ?
N3 C9 1.304(5) . ?
N3 C10 1.308(6) . ?
N4 C14 1.301(6) . ?
N4 C15 1.318(5) . ?
C1 C2 1.386(6) . ?
C1 C5 1.391(6) . ?
C2 C3 1.378(6) . ?
C4 C5 1.370(6) . ?
C6 C12 1.519(5) . ?
C6 C7 1.532(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.377(6) . ?
C7 C11 1.393(6) . ?
C8 C9 1.390(5) . ?
C10 C11 1.384(5) . ?
C12 C16 1.384(6) . ?
C12 C13 1.391(5) . ?
C13 C14 1.379(6) . ?
C15 C16 1.382(6) . ?
C17 C22 1.385(6) . ?
C17 C18 1.396(5) . ?
C18 C19 1.390(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 H22 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 N1 124.14(19) . . ?
O1 S1 C17 107.38(19) . . ?
N1 S1 C17 110.54(19) . . ?
O1 S1 C6 108.91(18) . . ?
N1 S1 C6 99.45(18) . . ?
C17 S1 C6 104.62(18) . . ?
C1 N1 S1 124.2(3) . . ?
C4 N2 C3 115.4(4) . . ?
C9 N3 C10 116.5(4) . . ?
C14 N4 C15 116.4(4) . . ?
C2 C1 C5 114.8(4) . . ?
C2 C1 N1 126.5(4) . . ?
C5 C1 N1 118.7(4) . . ?
F1 C2 C3 119.8(4) . . ?
F1 C2 C1 120.0(4) . . ?
C3 C2 C1 120.2(4) . . ?
N2 C3 F2 116.1(4) . . ?
N2 C3 C2 124.5(4) . . ?
F2 C3 C2 119.4(4) . . ?
N2 C4 F3 115.9(4) . . ?
N2 C4 C5 124.9(4) . . ?
F3 C4 C5 119.2(4) . . ?
F4 C5 C4 120.0(4) . . ?
F4 C5 C1 119.8(4) . . ?
C4 C5 C1 120.2(4) . . ?
C12 C6 C7 113.4(3) . . ?
C12 C6 S1 110.1(3) . . ?
C7 C6 S1 114.4(3) . . ?
C12 C6 H6 106.1 . . ?
C7 C6 H6 106.1 . . ?
S1 C6 H6 106.1 . . ?
C8 C7 C11 115.3(4) . . ?
C8 C7 C6 127.7(4) . . ?
C11 C7 C6 116.9(4) . . ?
F5 C8 C7 122.5(3) . . ?
F5 C8 C9 117.8(4) . . ?
C7 C8 C9 119.7(4) . . ?
N3 C9 F6 117.3(4) . . ?
N3 C9 C8 124.5(4) . . ?
F6 C9 C8 118.2(4) . . ?
N3 C10 F7 117.1(4) . . ?
N3 C10 C11 123.9(4) . . ?
F7 C10 C11 119.0(4) . . ?
F8 C11 C10 119.8(4) . . ?
F8 C11 C7 120.1(3) . . ?
C10 C11 C7 120.1(4) . . ?
C16 C12 C13 115.3(4) . . ?
C16 C12 C6 123.7(4) . . ?
C13 C12 C6 120.9(4) . . ?
F9 C13 C14 120.1(4) . . ?
F9 C13 C12 120.3(4) . . ?
C14 C13 C12 119.5(4) . . ?
N4 C14 F10 116.5(4) . . ?
N4 C14 C13 124.8(4) . . ?
F10 C14 C13 118.7(4) . . ?
N4 C15 F11 117.3(4) . . ?
N4 C15 C16 123.7(4) . . ?
F11 C15 C16 119.0(4) . . ?
F12 C16 C15 118.6(4) . . ?
F12 C16 C12 121.2(4) . . ?
C15 C16 C12 120.2(4) . . ?
C22 C17 C18 122.5(4) . . ?
C22 C17 S1 119.6(3) . . ?
C18 C17 S1 117.9(3) . . ?
C19 C18 C17 118.0(4) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 118.7(4) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_3t
_database_code_depnum_ccdc_archive 'CCDC 2027322'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_3q                  
;
PROBLEM: The value of Rint is greater than 0.12     Rint given   0.147
RESPONSE: The crystals supplied were weakly diffracting, even with 
prolonged exposure times.
;
_vrf_PLAT020_3q                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.147 Report
RESPONSE: The crystals supplied were weakly diffracting, even with 
prolonged exposure times.
;
_vrf_PLAT082_3q                  
;
PROBLEM: High R1 Value ..................................       0.11 Report
RESPONSE: The crystals supplied were weakly diffracting, even with 
prolonged exposure times.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3t
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 F4 N2 O S'
_chemical_formula_sum            'C12 H14 F4 N2 O S'
_chemical_formula_weight         310.31

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                   14.4786(9)
_cell_length_b                   20.0540(14)
_cell_length_c                   9.5173(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.638(3)
_cell_angle_gamma                90
_cell_volume                     2633.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5869
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.131

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14128
_diffrn_reflns_av_unetI/netI     0.2361
_diffrn_reflns_av_R_equivalents  0.1469
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_full        25.194
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4745
_reflns_number_gt                2114
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0554P)²+4.5327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4745
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2383
_refine_ls_R_factor_gt           0.1132
_refine_ls_wR_factor_ref         0.2166
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.07575(15) 0.82505(12) 0.54188(19) 0.0327(6) Uani 1 1 d . . . . .
F1 F 0.0089(3) 0.9392(2) 0.1549(4) 0.0426(13) Uani 1 1 d . . . . .
F2 F 0.1113(3) 0.9428(3) -0.0380(4) 0.0526(15) Uani 1 1 d . . . . .
F3 F 0.3318(3) 0.7977(3) 0.2330(5) 0.0515(15) Uani 1 1 d . . . . .
F4 F 0.2459(3) 0.7903(3) 0.4414(5) 0.0508(14) Uani 1 1 d . . . . .
O1 O 0.0831(4) 0.7532(3) 0.5378(5) 0.0443(16) Uani 1 1 d . . . . .
N1 N 0.0629(5) 0.8663(4) 0.4000(6) 0.041(2) Uani 1 1 d . . . . .
N2 N 0.2224(5) 0.8701(4) 0.0974(7) 0.0352(18) Uani 1 1 d . . . . .
C1 C 0.1218(6) 0.8640(4) 0.3091(7) 0.0249(19) Uani 1 1 d . . . . .
C2 C 0.0901(5) 0.9031(4) 0.1796(8) 0.028(2) Uani 1 1 d . . . . .
C3 C 0.1429(6) 0.9042(4) 0.0829(7) 0.029(2) Uani 1 1 d . . . . .
C4 C 0.2519(6) 0.8334(4) 0.2168(8) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.2064(6) 0.8300(4) 0.3232(8) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.1732(6) 0.8551(4) 0.6880(8) 0.044(3) Uani 1 1 d . . . . .
H6A H 0.173172 0.833105 0.779872 0.066 Uiso 1 1 calc R U . . .
H6B H 0.166325 0.903400 0.697745 0.066 Uiso 1 1 calc R U . . .
H6C H 0.234319 0.845695 0.667661 0.066 Uiso 1 1 calc R U . . .
C7 C -0.0323(6) 0.8473(4) 0.5851(8) 0.032(2) Uani 1 1 d . . . . .
H7 H -0.087745 0.830809 0.501532 0.039 Uiso 1 1 calc R U . . .
C8 C -0.0378(6) 0.8102(4) 0.7221(8) 0.045(3) Uani 1 1 d . . . . .
H8A H 0.016363 0.824378 0.808393 0.054 Uiso 1 1 calc R U . . .
H8B H -0.031632 0.761682 0.708221 0.054 Uiso 1 1 calc R U . . .
C9 C -0.1349(7) 0.8250(5) 0.7503(10) 0.058(3) Uani 1 1 d . . . . .
H9A H -0.188694 0.806480 0.668682 0.070 Uiso 1 1 calc R U . . .
H9B H -0.136154 0.803068 0.842927 0.070 Uiso 1 1 calc R U . . .
C10 C -0.1489(6) 0.8995(5) 0.7617(9) 0.054(3) Uani 1 1 d . . . . .
H10A H -0.212643 0.908177 0.776514 0.065 Uiso 1 1 calc R U . . .
H10B H -0.097956 0.917396 0.847853 0.065 Uiso 1 1 calc R U . . .
C11 C -0.1441(6) 0.9342(5) 0.6235(8) 0.045(3) Uani 1 1 d . . . . .
H11A H -0.153106 0.982732 0.633325 0.054 Uiso 1 1 calc R U . . .
H11B H -0.197528 0.917975 0.538481 0.054 Uiso 1 1 calc R U . . .
C12 C -0.0464(6) 0.9219(4) 0.5936(8) 0.036(2) Uani 1 1 d . . . . .
H12A H -0.046768 0.943225 0.499655 0.043 Uiso 1 1 calc R U . . .
H12B H 0.007244 0.941295 0.673952 0.043 Uiso 1 1 calc R U . . .
S2 S 0.51205(14) 0.67545(12) 0.36917(19) 0.0293(6) Uani 1 1 d . . . . .
F5 F 0.6081(3) 0.6722(3) 0.1368(4) 0.0453(13) Uani 1 1 d . . . . .
F6 F 0.6164(4) 0.6224(3) -0.1160(5) 0.0582(16) Uani 1 1 d . . . . .
F7 F 0.3374(4) 0.5075(3) -0.1915(5) 0.0619(16) Uani 1 1 d . . . . .
F8 F 0.3164(3) 0.5505(3) 0.0629(4) 0.0478(14) Uani 1 1 d . . . . .
O2 O 0.5407(4) 0.7418(3) 0.3414(5) 0.0395(15) Uani 1 1 d . . . . .
N3 N 0.4420(4) 0.6341(3) 0.2432(6) 0.0286(17) Uani 1 1 d . . . . .
N4 N 0.4753(6) 0.5663(4) -0.1571(7) 0.047(2) Uani 1 1 d . . . . .
C13 C 0.4602(6) 0.6146(4) 0.1160(7) 0.030(2) Uani 1 1 d . . . . .
C14 C 0.5366(6) 0.6326(4) 0.0615(8) 0.032(2) Uani 1 1 d . . . . .
C15 C 0.5403(6) 0.6054(5) -0.0725(8) 0.032(2) Uani 1 1 d . . . . .
C16 C 0.4042(7) 0.5490(5) -0.1075(8) 0.040(2) Uani 1 1 d . . . . .
C17 C 0.3920(6) 0.5716(4) 0.0214(8) 0.031(2) Uani 1 1 d . . . . .
C18 C 0.4461(5) 0.6792(4) 0.4975(7) 0.036(2) Uani 1 1 d . . . . .
H18A H 0.483971 0.703527 0.585460 0.054 Uiso 1 1 calc R U . . .
H18B H 0.433261 0.633924 0.525210 0.054 Uiso 1 1 calc R U . . .
H18C H 0.384586 0.702398 0.453001 0.054 Uiso 1 1 calc R U . . .
C19 C 0.6196(5) 0.6283(4) 0.4562(7) 0.029(2) Uani 1 1 d . . . . .
H19 H 0.651982 0.620241 0.378721 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6908(6) 0.6683(5) 0.5768(8) 0.045(2) Uani 1 1 d . . . . .
H20A H 0.662146 0.678095 0.656709 0.054 Uiso 1 1 calc R U . . .
H20B H 0.705288 0.711104 0.536322 0.054 Uiso 1 1 calc R U . . .
C21 C 0.7849(7) 0.6276(5) 0.6386(10) 0.056(3) Uani 1 1 d . . . . .
H21A H 0.817431 0.622971 0.561390 0.068 Uiso 1 1 calc R U . . .
H21B H 0.829332 0.651934 0.722731 0.068 Uiso 1 1 calc R U . . .
C22 C 0.7648(7) 0.5591(5) 0.6891(8) 0.054(3) Uani 1 1 d . . . . .
H22A H 0.826245 0.533669 0.722140 0.065 Uiso 1 1 calc R U . . .
H22B H 0.739656 0.563789 0.774411 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6932(7) 0.5211(5) 0.5699(9) 0.052(3) Uani 1 1 d . . . . .
H23A H 0.679497 0.477875 0.609548 0.062 Uiso 1 1 calc R U . . .
H23B H 0.721481 0.511818 0.489288 0.062 Uiso 1 1 calc R U . . .
C24 C 0.5982(6) 0.5599(4) 0.5079(8) 0.039(2) Uani 1 1 d . . . . .
H24A H 0.554170 0.535128 0.424269 0.047 Uiso 1 1 calc R U . . .
H24B H 0.565750 0.564940 0.585105 0.047 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 1.446(6) . ?
S1 N1 1.546(6) . ?
S1 C6 1.760(8) . ?
S1 C7 1.791(8) . ?
F1 C2 1.339(8) . ?
F2 C3 1.346(8) . ?
F3 C4 1.329(8) . ?
F4 C5 1.355(8) . ?
N1 C1 1.388(8) . ?
N2 C3 1.310(9) . ?
N2 C4 1.312(9) . ?
C1 C5 1.372(10) . ?
C1 C2 1.415(10) . ?
C2 C3 1.364(9) . ?
C4 C5 1.366(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.514(10) . ?
C7 C8 1.524(10) . ?
C7 H7 1.0000 . ?
C8 C9 1.538(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.508(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.545(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
S2 O2 1.442(6) . ?
S2 N3 1.554(6) . ?
S2 C18 1.765(6) . ?
S2 C19 1.795(8) . ?
F5 C14 1.328(9) . ?
F6 C15 1.334(8) . ?
F7 C16 1.340(9) . ?
F8 C17 1.341(8) . ?
N3 C13 1.372(8) . ?
N4 C15 1.300(10) . ?
N4 C16 1.302(10) . ?
C13 C14 1.403(10) . ?
C13 C17 1.411(10) . ?
C14 C15 1.403(10) . ?
C16 C17 1.368(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.518(10) . ?
C19 C24 1.520(10) . ?
C19 H19 1.0000 . ?
C20 C21 1.543(12) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.513(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.493(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.535(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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 N1 120.0(3) . . ?
O1 S1 C6 108.4(4) . . ?
N1 S1 C6 111.2(4) . . ?
O1 S1 C7 109.3(4) . . ?
N1 S1 C7 100.6(4) . . ?
C6 S1 C7 106.2(4) . . ?
C1 N1 S1 126.3(6) . . ?
C3 N2 C4 115.5(6) . . ?
C5 C1 N1 130.9(7) . . ?
C5 C1 C2 113.9(6) . . ?
N1 C1 C2 115.2(7) . . ?
F1 C2 C3 121.0(7) . . ?
F1 C2 C1 119.3(6) . . ?
C3 C2 C1 119.7(7) . . ?
N2 C3 F2 116.8(6) . . ?
N2 C3 C2 125.1(7) . . ?
F2 C3 C2 118.1(8) . . ?
N2 C4 F3 116.4(6) . . ?
N2 C4 C5 124.5(8) . . ?
F3 C4 C5 119.1(7) . . ?
F4 C5 C4 117.8(7) . . ?
F4 C5 C1 120.8(6) . . ?
C4 C5 C1 121.3(7) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 113.2(6) . . ?
C12 C7 S1 113.6(5) . . ?
C8 C7 S1 110.5(6) . . ?
C12 C7 H7 106.3 . . ?
C8 C7 H7 106.3 . . ?
S1 C7 H7 106.3 . . ?
C7 C8 C9 110.1(7) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 110.6(7) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 110.5(7) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.9(7) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C7 C12 C11 108.3(7) . . ?
C7 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C7 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O2 S2 N3 120.5(3) . . ?
O2 S2 C18 109.4(4) . . ?
N3 S2 C18 101.2(3) . . ?
O2 S2 C19 108.3(4) . . ?
N3 S2 C19 110.3(4) . . ?
C18 S2 C19 106.2(3) . . ?
C13 N3 S2 125.3(5) . . ?
C15 N4 C16 116.1(7) . . ?
N3 C13 C14 129.5(8) . . ?
N3 C13 C17 116.9(7) . . ?
C14 C13 C17 113.5(7) . . ?
F5 C14 C15 119.0(7) . . ?
F5 C14 C13 121.8(7) . . ?
C15 C14 C13 119.2(8) . . ?
N4 C15 F6 118.3(7) . . ?
N4 C15 C14 125.2(7) . . ?
F6 C15 C14 116.5(8) . . ?
N4 C16 F7 117.1(7) . . ?
N4 C16 C17 124.5(9) . . ?
F7 C16 C17 118.4(8) . . ?
F8 C17 C16 119.9(8) . . ?
F8 C17 C13 118.8(6) . . ?
C16 C17 C13 121.3(8) . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 112.9(6) . . ?
C20 C19 S2 111.5(6) . . ?
C24 C19 S2 113.0(5) . . ?
C20 C19 H19 106.3 . . ?
C24 C19 H19 106.3 . . ?
S2 C19 H19 106.3 . . ?
C19 C20 C21 109.2(7) . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C20 111.6(8) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 112.2(7) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C24 111.6(7) . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C19 C24 C23 109.6(7) . . ?
C19 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C19 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.095



