# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_1-pCF3
_database_code_depnum_ccdc_archive 'CCDC 1416199'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 S4'
_chemical_formula_sum            'C28 H12 F6 N4 S4'
_chemical_formula_weight         646.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   38.562(8)
_cell_length_b                   9.0853(19)
_cell_length_c                   7.0499(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.608(11)
_cell_angle_gamma                90
_cell_volume                     2467.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    2151
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.461
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            12561
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         25.500
_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             2287
_reflns_number_gt                1864
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+14.2219P] 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         2287
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 -0.03364(3) 0.35163(14) 0.0407(2) 0.0294(4) Uani 1 1 d . . . . .
N1 N 0.00521(10) 0.3019(4) -0.0070(6) 0.0263(10) Uani 1 1 d . . . . .
C1 C 0.00545(12) 0.1507(5) -0.0066(7) 0.0206(10) Uani 1 1 d . . . . .
C2 C -0.02854(11) 0.0888(5) 0.0381(7) 0.0215(11) Uani 1 1 d . . . . .
N2 N -0.05245(10) 0.1953(4) 0.0673(6) 0.0251(9) Uani 1 1 d . . . . .
C3 C 0.03490(12) 0.0647(5) -0.0457(7) 0.0204(10) Uani 1 1 d . . . . .
S2 S 0.07783(3) 0.31327(13) -0.06315(19) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.06845(12) 0.1268(5) -0.0914(7) 0.0209(10) Uani 1 1 d . . . . .
C5 C 0.09703(12) 0.0536(5) -0.1593(7) 0.0274(12) Uani 1 1 d . . . . .
H5 H 0.0973 -0.0492 -0.1843 0.033 Uiso 1 1 calc R U . . .
C6 C 0.12547(13) 0.1472(5) -0.1871(7) 0.0264(11) Uani 1 1 d . . . . .
H6 H 0.1468 0.1135 -0.2340 0.032 Uiso 1 1 calc R U . . .
C7 C 0.11971(12) 0.2916(5) -0.1405(7) 0.0229(11) Uani 1 1 d . . . . .
C8 C 0.14284(12) 0.4192(5) -0.1566(7) 0.0228(11) Uani 1 1 d . . . . .
C9 C 0.13061(13) 0.5631(5) -0.1354(7) 0.0265(11) Uani 1 1 d . . . . .
H9 H 0.1071 0.5783 -0.1061 0.032 Uiso 1 1 calc R U . . .
C10 C 0.15201(12) 0.6837(5) -0.1562(7) 0.0246(11) Uani 1 1 d . . . . .
H10 H 0.1431 0.7804 -0.1425 0.029 Uiso 1 1 calc R U . . .
C11 C 0.18660(13) 0.6630(5) -0.1972(7) 0.0261(11) Uani 1 1 d . . . . .
C12 C 0.19974(13) 0.5206(6) -0.2171(7) 0.0273(12) Uani 1 1 d . . . . .
H12 H 0.2233 0.5060 -0.2452 0.033 Uiso 1 1 calc R U . . .
C13 C 0.17798(12) 0.4012(6) -0.1953(7) 0.0260(11) Uani 1 1 d . . . . .
H13 H 0.1871 0.3045 -0.2068 0.031 Uiso 1 1 calc R U . . .
C14 C 0.20947(14) 0.7934(6) -0.2226(8) 0.0325(13) Uani 1 1 d . . . . .
F1 F 0.19436(10) 0.8958(4) -0.3333(7) 0.0853(16) Uani 1 1 d . . . . .
F2 F 0.21753(11) 0.8624(4) -0.0611(6) 0.0750(14) Uani 1 1 d . . . . .
F3 F 0.23937(9) 0.7621(4) -0.2994(6) 0.0623(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N2 1.610(4) . ?
S1 N1 1.615(4) . ?
N1 C1 1.373(6) . ?
C1 C3 1.416(6) . ?
C1 C2 1.473(6) . ?
C2 N2 1.359(6) . ?
C2 C3 1.418(6) 5 ?
C3 C2 1.418(6) 5 ?
C3 C4 1.461(6) . ?
S2 C7 1.739(5) . ?
S2 C4 1.742(5) . ?
C4 C5 1.391(7) . ?
C5 C6 1.409(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.470(6) . ?
C8 C9 1.400(7) . ?
C8 C13 1.404(7) . ?
C9 C10 1.384(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(7) . ?
C11 C14 1.493(7) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 F2 1.324(6) . ?
C14 F3 1.327(6) . ?
C14 F1 1.332(6) . ?

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
N2 S1 N1 101.8(2) . . ?
C1 N1 S1 106.6(3) . . ?
N1 C1 C3 123.8(4) . . ?
N1 C1 C2 112.1(4) . . ?
C3 C1 C2 124.1(4) . . ?
N2 C2 C3 125.1(4) . 5 ?
N2 C2 C1 112.2(4) . . ?
C3 C2 C1 122.7(4) 5 . ?
C2 N2 S1 107.3(3) . . ?
C1 C3 C2 113.2(4) . 5 ?
C1 C3 C4 123.8(4) . . ?
C2 C3 C4 123.0(4) 5 . ?
C7 S2 C4 92.6(2) . . ?
C5 C4 C3 127.9(4) . . ?
C5 C4 S2 109.9(3) . . ?
C3 C4 S2 122.1(3) . . ?
C4 C5 C6 113.1(4) . . ?
C4 C5 H5 123.4 . . ?
C6 C5 H5 123.4 . . ?
C7 C6 C5 114.1(4) . . ?
C7 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
C6 C7 C8 129.0(4) . . ?
C6 C7 S2 110.2(4) . . ?
C8 C7 S2 120.7(4) . . ?
C9 C8 C13 117.6(4) . . ?
C9 C8 C7 121.3(4) . . ?
C13 C8 C7 121.1(4) . . ?
C10 C9 C8 121.5(5) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.8(5) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 C14 119.7(5) . . ?
C12 C11 C14 120.2(4) . . ?
C13 C12 C11 119.3(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 121.7(5) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
F2 C14 F3 106.1(5) . . ?
F2 C14 F1 104.6(5) . . ?
F3 C14 F1 106.0(5) . . ?
F2 C14 C11 112.9(4) . . ?
F3 C14 C11 114.1(4) . . ?
F1 C14 C11 112.3(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 S1 N1 C1 0.6(4) . . . . ?
S1 N1 C1 C3 178.9(4) . . . . ?
S1 N1 C1 C2 -0.7(5) . . . . ?
N1 C1 C2 N2 0.4(6) . . . . ?
C3 C1 C2 N2 -179.2(4) . . . . ?
N1 C1 C2 C3 179.5(4) . . . 5 ?
C3 C1 C2 C3 -0.1(8) . . . 5 ?
C3 C2 N2 S1 -179.0(4) 5 . . . ?
C1 C2 N2 S1 0.0(5) . . . . ?
N1 S1 N2 C2 -0.4(4) . . . . ?
N1 C1 C3 C2 -179.5(4) . . . 5 ?
C2 C1 C3 C2 0.1(8) . . . 5 ?
N1 C1 C3 C4 -0.1(8) . . . . ?
C2 C1 C3 C4 179.5(5) . . . . ?
C1 C3 C4 C5 -169.4(5) . . . . ?
C2 C3 C4 C5 10.0(8) 5 . . . ?
C1 C3 C4 S2 11.2(7) . . . . ?
C2 C3 C4 S2 -169.5(4) 5 . . . ?
C7 S2 C4 C5 -0.3(4) . . . . ?
C7 S2 C4 C3 179.2(4) . . . . ?
C3 C4 C5 C6 -179.6(5) . . . . ?
S2 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C5 C6 C7 C8 -177.9(5) . . . . ?
C5 C6 C7 S2 -0.8(6) . . . . ?
C4 S2 C7 C6 0.7(4) . . . . ?
C4 S2 C7 C8 178.0(4) . . . . ?
C6 C7 C8 C9 168.1(5) . . . . ?
S2 C7 C8 C9 -8.7(7) . . . . ?
C6 C7 C8 C13 -11.4(8) . . . . ?
S2 C7 C8 C13 171.8(4) . . . . ?
C13 C8 C9 C10 1.5(7) . . . . ?
C7 C8 C9 C10 -178.0(5) . . . . ?
C8 C9 C10 C11 -0.7(8) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C9 C10 C11 C14 179.0(5) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C14 C11 C12 C13 -179.2(5) . . . . ?
C11 C12 C13 C8 1.0(8) . . . . ?
C9 C8 C13 C12 -1.7(7) . . . . ?
C7 C8 C13 C12 177.8(5) . . . . ?
C10 C11 C14 F2 72.1(6) . . . . ?
C12 C11 C14 F2 -108.7(6) . . . . ?
C10 C11 C14 F3 -166.6(5) . . . . ?
C12 C11 C14 F3 12.6(7) . . . . ?
C10 C11 C14 F1 -45.9(7) . . . . ?
C12 C11 C14 F1 133.2(5) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.084

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2-mCF3
_database_code_depnum_ccdc_archive 'CCDC 1416200'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 S4'
_chemical_formula_sum            'C28 H12 F6 N4 S4'
_chemical_formula_weight         646.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.0599(8)
_cell_length_b                   6.4683(13)
_cell_length_c                   20.014(3)
_cell_angle_alpha                93.915(15)
_cell_angle_beta                 97.142(13)
_cell_angle_gamma                102.709(14)
_cell_volume                     630.93(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      25.8
_cell_measurement_theta_max      29.8

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             326
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    4.134
_shelx_estimated_absorpt_T_min   0.232
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        -0.97
_diffrn_reflns_number            5134
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         67.989
_diffrn_reflns_theta_full        67.679
_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             2285
_reflns_number_gt                1877
_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       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'
_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)+(0.1029P)²+1.0937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2285
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1764
_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 0.8264(2) 0.12469(16) 0.06330(5) 0.0444(3) Uani 1 1 d . . . . .
S2 S 0.1497(2) 0.77357(16) 0.15098(5) 0.0424(3) Uani 1 1 d . . . . .
F1 F -0.4560(18) 0.5397(10) 0.4268(3) 0.201(4) Uani 1 1 d . . . . .
F2 F -0.1048(13) 0.6853(16) 0.4787(3) 0.202(4) Uani 1 1 d . . . . .
F3 F -0.4241(19) 0.8182(12) 0.4781(3) 0.211(4) Uani 1 1 d . . . . .
N1 N 0.6595(7) 0.2681(5) 0.10059(17) 0.0417(8) Uani 1 1 d . . . . .
N2 N 0.8017(7) 0.2002(5) -0.01129(17) 0.0411(8) Uani 1 1 d . . . . .
C1 C 0.5696(7) 0.3911(6) 0.05430(19) 0.0355(8) Uani 1 1 d . . . . .
C2 C 0.6518(8) 0.3511(6) -0.01105(19) 0.0357(8) Uani 1 1 d . . . . .
C3 C 0.4139(7) 0.5424(6) 0.06834(18) 0.0345(8) Uani 1 1 d . . . . .
C4 C 0.3312(8) 0.5811(6) 0.1339(2) 0.0387(8) Uani 1 1 d . . . . .
C5 C 0.3684(10) 0.4739(8) 0.1903(2) 0.0487(10) Uani 1 1 d . . . . .
H5 H 0.4610 0.3646 0.1918 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2536(10) 0.5452(7) 0.2451(2) 0.0494(11) Uani 1 1 d . . . . .
H6 H 0.2629 0.4875 0.2864 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1271(8) 0.7066(7) 0.2324(2) 0.0406(9) Uani 1 1 d . . . . .
C8 C -0.0185(9) 0.8155(7) 0.2777(2) 0.0426(9) Uani 1 1 d . . . . .
C9 C -0.0787(9) 0.7331(7) 0.3379(2) 0.0466(10) Uani 1 1 d . . . . .
H9 H -0.0205 0.6122 0.3499 0.056 Uiso 1 1 calc R U . . .
C10 C -0.2235(10) 0.8280(8) 0.3800(2) 0.0515(11) Uani 1 1 d . . . . .
C11 C -0.3090(11) 1.0101(8) 0.3640(2) 0.0573(12) Uani 1 1 d . . . . .
H11 H -0.4052 1.0747 0.3926 0.069 Uiso 1 1 calc R U . . .
C12 C -0.2481(12) 1.0930(8) 0.3047(3) 0.0607(13) Uani 1 1 d . . . . .
H12 H -0.3035 1.2155 0.2934 0.073 Uiso 1 1 calc R U . . .
C13 C -0.1065(10) 0.9982(7) 0.2618(2) 0.0532(11) Uani 1 1 d . . . . .
H13 H -0.0694 1.0566 0.2218 0.064 Uiso 1 1 calc R U . . .
C14 C -0.2980(13) 0.7259(10) 0.4416(3) 0.0668(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.593(3) . ?
S1 N2 1.601(3) . ?
S2 C7 1.725(4) . ?
S2 C4 1.741(4) . ?
F1 C14 1.283(8) . ?
F2 C14 1.239(7) . ?
F3 C14 1.233(7) . ?
N1 C1 1.361(5) . ?
N2 C2 1.362(5) . ?
C1 C3 1.419(5) . ?
C1 C2 1.445(5) . ?
C2 C3 1.419(5) 2_665 ?
C3 C2 1.419(5) 2_665 ?
C3 C4 1.448(5) . ?
C4 C5 1.380(6) . ?
C5 C6 1.400(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.473(6) . ?
C8 C9 1.391(6) . ?
C8 C13 1.394(6) . ?
C9 C10 1.381(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(7) . ?
C10 C14 1.488(7) . ?
C11 C12 1.377(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 N2 101.64(17) . . ?
C7 S2 C4 92.49(19) . . ?
C1 N1 S1 107.0(3) . . ?
C2 N2 S1 106.8(3) . . ?
N1 C1 C3 124.1(4) . . ?
N1 C1 C2 112.3(3) . . ?
C3 C1 C2 123.5(3) . . ?
N2 C2 C3 123.8(4) . 2_665 ?
N2 C2 C1 112.2(3) . . ?
C3 C2 C1 124.1(4) 2_665 . ?
C2 C3 C1 112.4(3) 2_665 . ?
C2 C3 C4 124.3(4) 2_665 . ?
C1 C3 C4 123.3(4) . . ?
C5 C4 C3 127.8(4) . . ?
C5 C4 S2 109.4(3) . . ?
C3 C4 S2 122.7(3) . . ?
C4 C5 C6 113.6(4) . . ?
C4 C5 H5 123.2 . . ?
C6 C5 H5 123.2 . . ?
C7 C6 C5 113.9(4) . . ?
C7 C6 H6 123.1 . . ?
C5 C6 H6 123.1 . . ?
C6 C7 C8 128.2(4) . . ?
C6 C7 S2 110.6(3) . . ?
C8 C7 S2 121.2(3) . . ?
C9 C8 C13 117.9(4) . . ?
C9 C8 C7 119.9(4) . . ?
C13 C8 C7 122.2(4) . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 C14 118.9(4) . . ?
C11 C10 C14 120.2(4) . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
F3 C14 F2 107.2(7) . . ?
F3 C14 F1 103.4(7) . . ?
F2 C14 F1 101.1(7) . . ?
F3 C14 C10 116.5(5) . . ?
F2 C14 C10 115.1(5) . . ?
F1 C14 C10 111.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 S1 N1 C1 -0.1(3) . . . . ?
N1 S1 N2 C2 -0.1(3) . . . . ?
S1 N1 C1 C3 -179.5(3) . . . . ?
S1 N1 C1 C2 0.2(4) . . . . ?
S1 N2 C2 C3 179.8(3) . . . 2_665 ?
S1 N2 C2 C1 0.2(4) . . . . ?
N1 C1 C2 N2 -0.3(5) . . . . ?
C3 C1 C2 N2 179.4(3) . . . . ?
N1 C1 C2 C3 -179.9(4) . . . 2_665 ?
C3 C1 C2 C3 -0.2(7) . . . 2_665 ?
N1 C1 C3 C2 179.8(4) . . . 2_665 ?
C2 C1 C3 C2 0.2(6) . . . 2_665 ?
N1 C1 C3 C4 -0.6(6) . . . . ?
C2 C1 C3 C4 179.7(4) . . . . ?
C2 C3 C4 C5 174.6(4) 2_665 . . . ?
C1 C3 C4 C5 -4.9(7) . . . . ?
C2 C3 C4 S2 -2.6(6) 2_665 . . . ?
C1 C3 C4 S2 177.8(3) . . . . ?
C7 S2 C4 C5 -0.1(3) . . . . ?
C7 S2 C4 C3 177.6(3) . . . . ?
C3 C4 C5 C6 -177.4(4) . . . . ?
S2 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 178.7(4) . . . . ?
C5 C6 C7 S2 -0.1(5) . . . . ?
C4 S2 C7 C6 0.1(4) . . . . ?
C4 S2 C7 C8 -178.7(4) . . . . ?
C6 C7 C8 C9 -10.8(7) . . . . ?
S2 C7 C8 C9 167.9(3) . . . . ?
C6 C7 C8 C13 170.9(5) . . . . ?
S2 C7 C8 C13 -10.4(6) . . . . ?
C13 C8 C9 C10 0.7(7) . . . . ?
C7 C8 C9 C10 -177.7(4) . . . . ?
C8 C9 C10 C11 -1.0(7) . . . . ?
C8 C9 C10 C14 176.2(5) . . . . ?
C9 C10 C11 C12 0.5(8) . . . . ?
C14 C10 C11 C12 -176.6(5) . . . . ?
C10 C11 C12 C13 0.3(8) . . . . ?
C11 C12 C13 C8 -0.6(8) . . . . ?
C9 C8 C13 C12 0.1(7) . . . . ?
C7 C8 C13 C12 178.4(5) . . . . ?
C9 C10 C14 F3 179.1(7) . . . . ?
C11 C10 C14 F3 -3.7(10) . . . . ?
C9 C10 C14 F2 52.4(9) . . . . ?
C11 C10 C14 F2 -130.4(7) . . . . ?
C9 C10 C14 F1 -62.2(8) . . . . ?
C11 C10 C14 F1 115.0(7) . . . . ?

_refine_diff_density_max         0.955
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_3-oCF3
_database_code_depnum_ccdc_archive 'CCDC 1416201'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 S4'
_chemical_formula_sum            'C28 H12 F6 N4 S4'
_chemical_formula_weight         646.66

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

_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'

loop_
_symmetry_equiv_pos_as_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                   4.859(4)
_cell_length_b                   22.931(18)
_cell_length_c                   22.781(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.026(12)
_cell_angle_gamma                90.00
_cell_volume                     2537(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5090
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      30.6

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28291
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4577
_reflns_number_gt                3509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0942P)²+3.8492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4577
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1942
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.1548(3) 0.83926(5) 0.74710(5) 0.0215(3) Uani 1 1 d . . .
N1 N 0.0178(8) 0.81147(17) 0.68865(18) 0.0204(9) Uani 1 1 d . . .
N2 N 0.3763(8) 0.88386(18) 0.72135(18) 0.0227(9) Uani 1 1 d . . .
C1 C 0.1418(10) 0.8374(2) 0.6424(2) 0.0202(11) Uani 1 1 d . . .
C2 C 0.0789(10) 0.8253(2) 0.5816(2) 0.0192(10) Uani 1 1 d . . .
C3 C 0.2404(10) 0.8580(2) 0.5432(2) 0.0188(10) Uani 1 1 d . . .
C4 C 0.4513(9) 0.9002(2) 0.5624(2) 0.0186(10) Uani 1 1 d . . .
C5 C 0.5147(9) 0.91202(19) 0.6225(2) 0.0167(10) Uani 1 1 d . . .
C6 C 0.3534(10) 0.8794(2) 0.6616(2) 0.0189(10) Uani 1 1 d . . .
S2 S 0.4378(3) 0.89817(5) 0.45745(5) 0.0229(3) Uani 1 1 d . . .
N3 N 0.5784(8) 0.92527(17) 0.51589(17) 0.0211(9) Uani 1 1 d . . .
N4 N 0.2150(9) 0.85434(17) 0.48327(17) 0.0216(9) Uani 1 1 d . . .
S3 S -0.1676(2) 0.76424(5) 0.48826(5) 0.0202(3) Uani 1 1 d . . .
C7 C -0.1252(10) 0.7820(2) 0.5624(2) 0.0178(10) Uani 1 1 d . . .
C8 C -0.2952(10) 0.7479(2) 0.5957(2) 0.0206(11) Uani 1 1 d . . .
H8 H -0.3058 0.7516 0.6371 0.025 Uiso 1 1 calc R . .
C9 C -0.4510(10) 0.7072(2) 0.5623(2) 0.0209(10) Uani 1 1 d . . .
H9 H -0.5774 0.6806 0.5787 0.025 Uiso 1 1 calc R . .
C10 C -0.3997(9) 0.7101(2) 0.5034(2) 0.0197(10) Uani 1 1 d . . .
C11 C -0.5177(10) 0.6742(2) 0.4544(2) 0.0198(10) Uani 1 1 d . . .
C12 C -0.4831(10) 0.6131(2) 0.4514(2) 0.0195(10) Uani 1 1 d . . .
C13 C -0.6077(10) 0.5811(2) 0.4060(2) 0.0238(11) Uani 1 1 d . . .
H13 H -0.5856 0.5399 0.4047 0.029 Uiso 1 1 calc R . .
C14 C -0.7653(11) 0.6094(2) 0.3623(2) 0.0248(11) Uani 1 1 d . . .
H14 H -0.8546 0.5874 0.3318 0.030 Uiso 1 1 calc R . .
C15 C -0.7917(11) 0.6695(2) 0.3631(2) 0.0282(12) Uani 1 1 d . . .
H15 H -0.8949 0.6888 0.3327 0.034 Uiso 1 1 calc R . .
C16 C -0.6680(10) 0.7013(2) 0.4082(2) 0.0217(11) Uani 1 1 d . . .
H16 H -0.6849 0.7426 0.4080 0.026 Uiso 1 1 calc R . .
C17 C -0.3057(10) 0.5819(2) 0.4965(2) 0.0216(11) Uani 1 1 d . . .
F1 F -0.0631(6) 0.60863(12) 0.50834(13) 0.0277(7) Uani 1 1 d . . .
F2 F -0.4274(6) 0.57554(12) 0.54854(12) 0.0253(7) Uani 1 1 d . . .
F3 F -0.2411(6) 0.52724(12) 0.47883(14) 0.0311(7) Uani 1 1 d . . .
S4 S 0.7540(2) 0.97594(5) 0.71579(5) 0.0206(3) Uani 1 1 d . . .
C18 C 0.7184(10) 0.9556(2) 0.6422(2) 0.0198(11) Uani 1 1 d . . .
C19 C 0.8992(10) 0.9878(2) 0.6095(2) 0.0222(11) Uani 1 1 d . . .
H19 H 0.9142 0.9831 0.5683 0.027 Uiso 1 1 calc R . .
C20 C 1.0585(10) 1.0281(2) 0.6425(2) 0.0218(11) Uani 1 1 d . . .
H20 H 1.1906 1.0532 0.6259 0.026 Uiso 1 1 calc R . .
C21 C 1.0027(10) 1.0274(2) 0.7011(2) 0.0191(10) Uani 1 1 d . . .
C22 C 1.1342(10) 1.0602(2) 0.7505(2) 0.0204(11) Uani 1 1 d . . .
C23 C 1.1706(10) 1.1212(2) 0.7505(2) 0.0222(11) Uani 1 1 d . . .
C24 C 1.3196(11) 1.1481(2) 0.7969(2) 0.0275(12) Uani 1 1 d . . .
H24 H 1.3476 1.1891 0.7962 0.033 Uiso 1 1 calc R . .
C25 C 1.4261(11) 1.1158(2) 0.8435(2) 0.0270(12) Uani 1 1 d . . .
H25 H 1.5322 1.1343 0.8739 0.032 Uiso 1 1 calc R . .
C26 C 1.3778(11) 1.0560(2) 0.8457(2) 0.0243(11) Uani 1 1 d . . .
H26 H 1.4433 1.0340 0.8787 0.029 Uiso 1 1 calc R . .
C27 C 1.2338(10) 1.0284(2) 0.7998(2) 0.0220(11) Uani 1 1 d . . .
H27 H 1.2020 0.9876 0.8016 0.026 Uiso 1 1 calc R . .
C28 C 1.0524(12) 1.1592(2) 0.7025(2) 0.0315(13) Uani 1 1 d . . .
F4 F 0.7958(6) 1.14360(13) 0.68444(14) 0.0351(8) Uani 1 1 d . . .
F5 F 1.2035(7) 1.16048(14) 0.65404(14) 0.0396(8) Uani 1 1 d . . .
F6 F 1.0302(8) 1.21513(13) 0.72013(15) 0.0497(10) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.600(4) . ?
S1 N2 1.610(4) . ?
N1 C1 1.368(6) . ?
N2 C6 1.365(6) . ?
C1 C2 1.436(7) . ?
C1 C6 1.464(7) . ?
C2 C3 1.411(7) . ?
C2 C7 1.459(7) . ?
C3 N4 1.369(6) . ?
C3 C4 1.464(7) . ?
C4 N3 1.372(6) . ?
C4 C5 1.418(6) . ?
C5 C6 1.421(7) . ?
C5 C18 1.465(7) . ?
S2 N3 1.601(4) . ?
S2 N4 1.604(4) . ?
S3 C10 1.720(5) . ?
S3 C7 1.742(5) . ?
C7 C8 1.384(7) . ?
C8 C9 1.408(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.486(7) . ?
C11 C16 1.405(7) . ?
C11 C12 1.413(7) . ?
C12 C13 1.390(7) . ?
C12 C17 1.500(7) . ?
C13 C14 1.395(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 F1 1.347(6) . ?
C17 F2 1.352(6) . ?
C17 F3 1.357(6) . ?
S4 C21 1.730(5) . ?
S4 C18 1.743(5) . ?
C18 C19 1.386(7) . ?
C19 C20 1.406(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.481(7) . ?
C22 C23 1.409(7) . ?
C22 C27 1.409(7) . ?
C23 C24 1.402(7) . ?
C23 C28 1.499(7) . ?
C24 C25 1.380(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 F4 1.348(6) . ?
C28 F5 1.348(7) . ?
C28 F6 1.349(6) . ?

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
N1 S1 N2 102.3(2) . . ?
C1 N1 S1 106.6(3) . . ?
C6 N2 S1 106.4(3) . . ?
N1 C1 C2 125.1(4) . . ?
N1 C1 C6 112.3(4) . . ?
C2 C1 C6 122.6(4) . . ?
C3 C2 C1 113.0(4) . . ?
C3 C2 C7 124.3(4) . . ?
C1 C2 C7 122.6(4) . . ?
N4 C3 C2 123.5(4) . . ?
N4 C3 C4 112.1(4) . . ?
C2 C3 C4 124.4(4) . . ?
N3 C4 C5 125.2(4) . . ?
N3 C4 C3 112.0(4) . . ?
C5 C4 C3 122.7(4) . . ?
C4 C5 C6 113.5(4) . . ?
C4 C5 C18 123.2(4) . . ?
C6 C5 C18 123.2(4) . . ?
N2 C6 C5 123.9(4) . . ?
N2 C6 C1 112.3(4) . . ?
C5 C6 C1 123.8(4) . . ?
N3 S2 N4 102.2(2) . . ?
C4 N3 S2 106.8(3) . . ?
C3 N4 S2 106.8(3) . . ?
C10 S3 C7 91.7(2) . . ?
C8 C7 C2 129.3(4) . . ?
C8 C7 S3 110.3(3) . . ?
C2 C7 S3 120.4(4) . . ?
C7 C8 C9 113.5(4) . . ?
C7 C8 H8 123.2 . . ?
C9 C8 H8 123.2 . . ?
C10 C9 C8 112.4(4) . . ?
C10 C9 H9 123.8 . . ?
C8 C9 H9 123.8 . . ?
C9 C10 C11 128.9(5) . . ?
C9 C10 S3 112.0(4) . . ?
C11 C10 S3 119.2(4) . . ?
C16 C11 C12 117.5(4) . . ?
C16 C11 C10 119.6(4) . . ?
C12 C11 C10 122.9(4) . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 C17 118.8(4) . . ?
C11 C12 C17 120.4(4) . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.7(5) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
F1 C17 F2 106.2(4) . . ?
F1 C17 F3 105.7(4) . . ?
F2 C17 F3 105.9(4) . . ?
F1 C17 C12 113.5(4) . . ?
F2 C17 C12 113.2(4) . . ?
F3 C17 C12 111.8(4) . . ?
C21 S4 C18 92.5(2) . . ?
C19 C18 C5 129.3(4) . . ?
C19 C18 S4 109.3(4) . . ?
C5 C18 S4 121.4(4) . . ?
C18 C19 C20 114.3(4) . . ?
C18 C19 H19 122.9 . . ?
C20 C19 H19 122.9 . . ?
C21 C20 C19 112.8(4) . . ?
C21 C20 H20 123.6 . . ?
C19 C20 H20 123.6 . . ?
C20 C21 C22 129.7(5) . . ?
C20 C21 S4 111.1(4) . . ?
C22 C21 S4 119.0(4) . . ?
C23 C22 C27 118.3(4) . . ?
C23 C22 C21 123.7(4) . . ?
C27 C22 C21 118.0(4) . . ?
C24 C23 C22 119.9(5) . . ?
C24 C23 C28 117.8(4) . . ?
C22 C23 C28 122.2(4) . . ?
C25 C24 C23 120.7(5) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.9(5) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.0(5) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 120.9(5) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
F4 C28 F5 106.3(4) . . ?
F4 C28 F6 105.1(5) . . ?
F5 C28 F6 106.0(4) . . ?
F4 C28 C23 113.2(4) . . ?
F5 C28 C23 113.9(5) . . ?
F6 C28 C23 111.7(4) . . ?

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
N2 S1 N1 C1 -0.8(4) . . . . ?
N1 S1 N2 C6 0.2(4) . . . . ?
S1 N1 C1 C2 -179.6(4) . . . . ?
S1 N1 C1 C6 1.0(5) . . . . ?
N1 C1 C2 C3 -179.4(4) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
N1 C1 C2 C7 -1.5(7) . . . . ?
C6 C1 C2 C7 177.8(4) . . . . ?
C1 C2 C3 N4 -179.3(4) . . . . ?
C7 C2 C3 N4 2.8(7) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C7 C2 C3 C4 -178.0(4) . . . . ?
N4 C3 C4 N3 -1.3(6) . . . . ?
C2 C3 C4 N3 179.4(4) . . . . ?
N4 C3 C4 C5 179.6(4) . . . . ?
C2 C3 C4 C5 0.4(7) . . . . ?
N3 C4 C5 C6 -179.2(4) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
N3 C4 C5 C18 3.3(7) . . . . ?
C3 C4 C5 C18 -177.8(4) . . . . ?
S1 N2 C6 C5 179.9(4) . . . . ?
S1 N2 C6 C1 0.4(5) . . . . ?
C4 C5 C6 N2 -179.4(4) . . . . ?
C18 C5 C6 N2 -1.9(7) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C18 C5 C6 C1 177.5(4) . . . . ?
N1 C1 C6 N2 -1.0(6) . . . . ?
C2 C1 C6 N2 179.7(4) . . . . ?
N1 C1 C6 C5 179.5(4) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C5 C4 N3 S2 179.8(4) . . . . ?
C3 C4 N3 S2 0.8(5) . . . . ?
N4 S2 N3 C4 -0.1(4) . . . . ?
C2 C3 N4 S2 -179.6(4) . . . . ?
C4 C3 N4 S2 1.1(5) . . . . ?
N3 S2 N4 C3 -0.6(4) . . . . ?
C3 C2 C7 C8 -179.6(5) . . . . ?
C1 C2 C7 C8 2.7(8) . . . . ?
C3 C2 C7 S3 4.2(6) . . . . ?
C1 C2 C7 S3 -173.6(4) . . . . ?
C10 S3 C7 C8 -2.1(4) . . . . ?
C10 S3 C7 C2 174.7(4) . . . . ?
C2 C7 C8 C9 -175.0(4) . . . . ?
S3 C7 C8 C9 1.6(5) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 178.8(5) . . . . ?
C8 C9 C10 S3 -1.7(5) . . . . ?
C7 S3 C10 C9 2.2(4) . . . . ?
C7 S3 C10 C11 -178.3(4) . . . . ?
C9 C10 C11 C16 119.7(6) . . . . ?
S3 C10 C11 C16 -59.7(6) . . . . ?
C9 C10 C11 C12 -61.1(7) . . . . ?
S3 C10 C11 C12 119.5(5) . . . . ?
C16 C11 C12 C13 -3.7(7) . . . . ?
C10 C11 C12 C13 177.1(5) . . . . ?
C16 C11 C12 C17 174.9(4) . . . . ?
C10 C11 C12 C17 -4.2(7) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
C17 C12 C13 C14 -177.6(5) . . . . ?
C12 C13 C14 C15 1.7(8) . . . . ?
C13 C14 C15 C16 -1.7(8) . . . . ?
C14 C15 C16 C11 -1.1(8) . . . . ?
C12 C11 C16 C15 3.7(7) . . . . ?
C10 C11 C16 C15 -177.1(5) . . . . ?
C13 C12 C17 F1 133.5(5) . . . . ?
C11 C12 C17 F1 -45.2(6) . . . . ?
C13 C12 C17 F2 -105.4(5) . . . . ?
C11 C12 C17 F2 76.0(6) . . . . ?
C13 C12 C17 F3 14.1(6) . . . . ?
C11 C12 C17 F3 -164.6(4) . . . . ?
C4 C5 C18 C19 -6.9(8) . . . . ?
C6 C5 C18 C19 175.9(5) . . . . ?
C4 C5 C18 S4 170.7(4) . . . . ?
C6 C5 C18 S4 -6.5(6) . . . . ?
C21 S4 C18 C19 0.9(4) . . . . ?
C21 S4 C18 C5 -177.1(4) . . . . ?
C5 C18 C19 C20 177.0(5) . . . . ?
S4 C18 C19 C20 -0.8(5) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C19 C20 C21 C22 176.3(5) . . . . ?
C19 C20 C21 S4 0.6(5) . . . . ?
C18 S4 C21 C20 -0.9(4) . . . . ?
C18 S4 C21 C22 -177.1(4) . . . . ?
C20 C21 C22 C23 51.7(8) . . . . ?
S4 C21 C22 C23 -132.9(5) . . . . ?
C20 C21 C22 C27 -126.9(6) . . . . ?
S4 C21 C22 C27 48.5(6) . . . . ?
C27 C22 C23 C24 4.4(7) . . . . ?
C21 C22 C23 C24 -174.2(5) . . . . ?
C27 C22 C23 C28 -175.0(5) . . . . ?
C21 C22 C23 C28 6.4(8) . . . . ?
C22 C23 C24 C25 -1.6(8) . . . . ?
C28 C23 C24 C25 177.9(5) . . . . ?
C23 C24 C25 C26 -2.2(8) . . . . ?
C24 C25 C26 C27 3.1(8) . . . . ?
C25 C26 C27 C22 -0.1(8) . . . . ?
C23 C22 C27 C26 -3.6(7) . . . . ?
C21 C22 C27 C26 175.1(5) . . . . ?
C24 C23 C28 F4 -138.7(5) . . . . ?
C22 C23 C28 F4 40.7(7) . . . . ?
C24 C23 C28 F5 99.7(6) . . . . ?
C22 C23 C28 F5 -80.8(6) . . . . ?
C24 C23 C28 F6 -20.3(7) . . . . ?
C22 C23 C28 F6 159.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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-pOCF3
_database_code_depnum_ccdc_archive 'CCDC 1416202'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
; # start Validation Reply Form
_vrf_PLAT340_4-pOCF3             
;
PROBLEM: Low Bond Precision on C-C Bonds .. 0.0132 Ang.
RESPONSE: The crystal presents too thin, resulting in poor diffraction data. 
These factors contribute to the increasing of uncertainty on the atom positions. 
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 O2 S4'
_chemical_formula_sum            'C28 H12 F6 N4 O2 S4'
_chemical_formula_weight         678.66

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

loop_
_symmetry_equiv_pos_as_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'
'-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                   40.73(7)
_cell_length_b                   9.045(15)
_cell_length_c                   7.129(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.19(3)
_cell_angle_gamma                90.00
_cell_volume                     2616(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2046
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12157
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2431
_reflns_number_gt                1642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1212P)²+66.6524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2431
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.1264
_refine_ls_wR_factor_ref         0.3288
_refine_ls_wR_factor_gt          0.2980
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03178(6) 0.6446(3) 0.0656(4) 0.0368(7) Uani 1 1 d . . .
N1 N 0.04975(19) 0.8013(9) 0.1064(11) 0.0283(18) Uani 1 1 d . . .
C1 C 0.0269(2) 0.9086(10) 0.0588(12) 0.024(2) Uani 1 1 d . . .
C2 C -0.0053(2) 0.8464(10) -0.0131(13) 0.027(2) Uani 1 1 d . . .
N2 N -0.00514(19) 0.6939(9) -0.0132(12) 0.0301(18) Uani 1 1 d . . .
C3 C 0.0334(2) 1.0635(11) 0.0735(12) 0.029(2) Uani 1 1 d . . .
S2 S 0.07477(6) 1.3140(3) 0.1261(4) 0.0310(7) Uani 1 1 d . . .
C4 C 0.0651(2) 1.1252(11) 0.1429(12) 0.026(2) Uani 1 1 d . . .
C5 C 0.0925(2) 1.0487(11) 0.2362(13) 0.031(2) Uani 1 1 d . . .
H5 H 0.0925 0.9457 0.2618 0.037 Uiso 1 1 calc R . .
C6 C 0.1195(2) 1.1419(11) 0.2863(14) 0.032(2) Uani 1 1 d . . .
H6 H 0.1395 1.1071 0.3495 0.039 Uiso 1 1 calc R . .
C7 C 0.1144(2) 1.2888(11) 0.2360(13) 0.028(2) Uani 1 1 d . . .
C8 C 0.1370(2) 1.4177(11) 0.2682(12) 0.030(2) Uani 1 1 d . . .
C9 C 0.1257(2) 1.5644(11) 0.2490(14) 0.032(2) Uani 1 1 d . . .
H9 H 0.1032 1.5816 0.2087 0.038 Uiso 1 1 calc R . .
C10 C 0.1465(2) 1.6863(12) 0.2869(14) 0.034(2) Uani 1 1 d . . .
H10 H 0.1385 1.7846 0.2722 0.041 Uiso 1 1 calc R . .
C11 C 0.1799(2) 1.6573(11) 0.3479(15) 0.033(2) Uani 1 1 d . . .
C12 C 0.1917(2) 1.5122(12) 0.3639(13) 0.033(2) Uani 1 1 d . . .
H12 H 0.2144 1.4943 0.4018 0.040 Uiso 1 1 calc R . .
C13 C 0.1705(2) 1.3950(11) 0.3244(14) 0.031(2) Uani 1 1 d . . .
H13 H 0.1787 1.2969 0.3356 0.037 Uiso 1 1 calc R . .
O1 O 0.20106(18) 1.7735(8) 0.4067(11) 0.0425(19) Uani 1 1 d . . .
F1 F 0.19014(18) 1.9191(9) 0.1515(11) 0.069(2) Uani 1 1 d . . .
F2 F 0.23309(16) 1.9613(7) 0.3550(10) 0.0537(19) Uani 1 1 d . . .
F3 F 0.23088(19) 1.7695(8) 0.1597(12) 0.067(2) Uani 1 1 d . . .
C14 C 0.2127(3) 1.8485(13) 0.2733(16) 0.044(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.610(8) . ?
S1 N2 1.619(8) . ?
N1 C1 1.365(12) . ?
C1 C3 1.427(14) . ?
C1 C2 1.477(13) . ?
C2 N2 1.379(12) . ?
C2 C3 1.438(13) 5_575 ?
C3 C2 1.438(13) 5_575 ?
C3 C4 1.454(13) . ?
S2 C7 1.745(9) . ?
S2 C4 1.758(10) . ?
C4 C5 1.424(12) . ?
C5 C6 1.404(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.489(13) . ?
C8 C13 1.401(13) . ?
C8 C9 1.407(14) . ?
C9 C10 1.401(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.414(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(14) . ?
C11 O1 1.399(11) . ?
C12 C13 1.382(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1 C14 1.293(14) . ?
F1 C14 1.365(13) . ?
F2 C14 1.407(12) . ?
F3 C14 1.349(14) . ?

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
N1 S1 N2 102.3(4) . . ?
C1 N1 S1 107.0(6) . . ?
N1 C1 C3 124.3(8) . . ?
N1 C1 C2 112.3(8) . . ?
C3 C1 C2 123.4(8) . . ?
N2 C2 C3 124.8(9) . 5_575 ?
N2 C2 C1 112.1(8) . . ?
C3 C2 C1 123.1(8) 5_575 . ?
C2 N2 S1 106.2(6) . . ?
C1 C3 C2 113.5(8) . 5_575 ?
C1 C3 C4 123.6(8) . . ?
C2 C3 C4 122.9(9) 5_575 . ?
C7 S2 C4 92.6(4) . . ?
C5 C4 C3 127.3(9) . . ?
C5 C4 S2 109.5(7) . . ?
C3 C4 S2 123.2(7) . . ?
C6 C5 C4 112.8(9) . . ?
C6 C5 H5 123.6 . . ?
C4 C5 H5 123.6 . . ?
C7 C6 C5 114.5(8) . . ?
C7 C6 H6 122.7 . . ?
C5 C6 H6 122.7 . . ?
C6 C7 C8 129.4(8) . . ?
C6 C7 S2 110.5(7) . . ?
C8 C7 S2 120.0(7) . . ?
C13 C8 C9 117.7(9) . . ?
C13 C8 C7 120.1(9) . . ?
C9 C8 C7 122.2(9) . . ?
C10 C9 C8 122.5(9) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 117.5(10) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C12 C11 O1 118.8(8) . . ?
C12 C11 C10 120.9(9) . . ?
O1 C11 C10 120.1(9) . . ?
C13 C12 C11 119.8(9) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 121.5(9) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C14 O1 C11 115.6(9) . . ?
O1 C14 F3 114.9(10) . . ?
O1 C14 F1 116.2(10) . . ?
F3 C14 F1 103.9(9) . . ?
O1 C14 F2 108.5(9) . . ?
F3 C14 F2 107.4(9) . . ?
F1 C14 F2 105.2(9) . . ?

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
N2 S1 N1 C1 0.0(7) . . . . ?
S1 N1 C1 C3 -179.6(7) . . . . ?
S1 N1 C1 C2 -0.5(9) . . . . ?
N1 C1 C2 N2 0.9(11) . . . . ?
C3 C1 C2 N2 180.0(8) . . . . ?
N1 C1 C2 C3 -179.7(8) . . . 5_575 ?
C3 C1 C2 C3 -0.5(16) . . . 5_575 ?
C3 C2 N2 S1 179.7(8) 5_575 . . . ?
C1 C2 N2 S1 -0.8(10) . . . . ?
N1 S1 N2 C2 0.5(7) . . . . ?
N1 C1 C3 C2 179.5(8) . . . 5_575 ?
C2 C1 C3 C2 0.5(14) . . . 5_575 ?
N1 C1 C3 C4 -0.5(15) . . . . ?
C2 C1 C3 C4 -179.5(8) . . . . ?
C1 C3 C4 C5 -11.9(15) . . . . ?
C2 C3 C4 C5 168.0(9) 5_575 . . . ?
C1 C3 C4 S2 169.6(7) . . . . ?
C2 C3 C4 S2 -10.4(13) 5_575 . . . ?
C7 S2 C4 C5 1.2(7) . . . . ?
C7 S2 C4 C3 179.9(8) . . . . ?
C3 C4 C5 C6 -179.5(9) . . . . ?
S2 C4 C5 C6 -0.9(11) . . . . ?
C4 C5 C6 C7 0.0(13) . . . . ?
C5 C6 C7 C8 179.1(9) . . . . ?
C5 C6 C7 S2 0.9(12) . . . . ?
C4 S2 C7 C6 -1.2(8) . . . . ?
C4 S2 C7 C8 -179.5(8) . . . . ?
C6 C7 C8 C13 13.6(15) . . . . ?
S2 C7 C8 C13 -168.4(7) . . . . ?
C6 C7 C8 C9 -164.6(10) . . . . ?
S2 C7 C8 C9 13.3(12) . . . . ?
C13 C8 C9 C10 -1.2(14) . . . . ?
C7 C8 C9 C10 177.1(9) . . . . ?
C8 C9 C10 C11 -0.5(15) . . . . ?
C9 C10 C11 C12 1.9(15) . . . . ?
C9 C10 C11 O1 -173.4(9) . . . . ?
O1 C11 C12 C13 173.6(9) . . . . ?
C10 C11 C12 C13 -1.7(15) . . . . ?
C11 C12 C13 C8 0.0(15) . . . . ?
C9 C8 C13 C12 1.4(14) . . . . ?
C7 C8 C13 C12 -176.9(9) . . . . ?
C12 C11 O1 C14 104.4(12) . . . . ?
C10 C11 O1 C14 -80.2(13) . . . . ?
C11 O1 C14 F3 -60.4(12) . . . . ?
C11 O1 C14 F1 61.1(13) . . . . ?
C11 O1 C14 F2 179.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.111
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.159
####################################################################### 
# 
# 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_5-mOCF
_database_code_depnum_ccdc_archive 'CCDC 1416203'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 O2 S4'
_chemical_formula_sum            'C28 H12 F6 N4 O2 S4'
_chemical_formula_weight         678.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   4.8806(19)
_cell_length_b                   6.618(3)
_cell_length_c                   20.996(10)
_cell_angle_alpha                96.69(3)
_cell_angle_beta                 94.33(4)
_cell_angle_gamma                103.15(3)
_cell_volume                     652.2(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      25.2
_cell_measurement_theta_max      29.6

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    4.093
_shelx_estimated_absorpt_T_min   0.234
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        -0.29
_diffrn_reflns_number            5328
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         67.886
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2361
_reflns_number_gt                1485
_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       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'
_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)+(0.1366P)²+0.6429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2361
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.1937
_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 0.3271(3) 0.6434(2) 0.56150(7) 0.0488(4) Uani 1 1 d . . . . .
S2 S 0.3408(3) 0.6840(2) 0.35432(7) 0.0478(4) Uani 1 1 d . . . . .
F1 F 0.9928(15) 0.8948(11) 0.0935(3) 0.128(2) Uani 1 1 d . . . . .
F2 F 0.6012(15) 0.8609(10) 0.0514(3) 0.129(2) Uani 1 1 d . . . . .
F3 F 0.8764(17) 0.7573(9) -0.0057(3) 0.132(3) Uani 1 1 d . . . . .
O1 O 0.7123(18) 0.5731(8) 0.0658(3) 0.108(2) Uani 1 1 d . . . . .
N1 N 0.2994(10) 0.6944(7) 0.4896(2) 0.0453(11) Uani 1 1 d . . . . .
N2 N 0.1636(10) 0.7966(7) 0.5974(2) 0.0470(11) Uani 1 1 d . . . . .
C1 C 0.1498(11) 0.8474(7) 0.4897(3) 0.0412(12) Uani 1 1 d . . . . .
C2 C 0.0716(11) 0.9083(7) 0.5527(2) 0.0397(11) Uani 1 1 d . . . . .
C3 C 0.0820(11) 0.9356(8) 0.4337(3) 0.0414(11) Uani 1 1 d . . . . .
C4 C 0.1598(12) 0.8788(8) 0.3707(3) 0.0428(12) Uani 1 1 d . . . . .
C5 C 0.1178(15) 0.9661(10) 0.3152(3) 0.0577(15) Uani 1 1 d . . . . .
H5 H 0.0252 1.0739 0.3134 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2273(14) 0.8779(10) 0.2619(3) 0.0554(15) Uani 1 1 d . . . . .
H6 H 0.2145 0.9216 0.2215 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3535(12) 0.7229(8) 0.2748(3) 0.0465(12) Uani 1 1 d . . . . .
C8 C 0.4966(13) 0.5973(8) 0.2311(3) 0.0486(13) Uani 1 1 d . . . . .
C9 C 0.5331(16) 0.6485(9) 0.1700(3) 0.0614(17) Uani 1 1 d . . . . .
H9 H 0.4642 0.7575 0.1560 0.074 Uiso 1 1 calc R U . . .
C10 C 0.6740(17) 0.5353(10) 0.1295(3) 0.0653(18) Uani 1 1 d . . . . .
C11 C 0.7699(17) 0.3704(10) 0.1470(3) 0.0692(19) Uani 1 1 d . . . . .
H11 H 0.8621 0.2955 0.1191 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7254(18) 0.3184(11) 0.2079(3) 0.072(2) Uani 1 1 d . . . . .
H12 H 0.7883 0.2058 0.2210 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5903(15) 0.4288(10) 0.2494(3) 0.0614(16) Uani 1 1 d . . . . .
H13 H 0.5620 0.3899 0.2900 0.074 Uiso 1 1 calc R U . . .
C14 C 0.805(2) 0.7585(12) 0.0509(4) 0.079(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N2 1.585(5) . ?
S1 N1 1.587(5) . ?
S2 C7 1.723(6) . ?
S2 C4 1.738(5) . ?
F1 C14 1.329(10) . ?
F2 C14 1.325(10) . ?
F3 C14 1.263(8) . ?
O1 C14 1.291(9) . ?
O1 C10 1.407(8) . ?
N1 C1 1.377(7) . ?
N2 C2 1.370(7) . ?
C1 C3 1.422(7) . ?
C1 C2 1.444(7) . ?
C2 C3 1.423(7) 2_576 ?
C3 C2 1.423(7) 2_576 ?
C3 C4 1.434(7) . ?
C4 C5 1.382(8) . ?
C5 C6 1.399(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.353(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(8) . ?
C8 C13 1.380(8) . ?
C8 C9 1.380(8) . ?
C9 C10 1.389(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(10) . ?
C11 C12 1.381(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 N1 102.1(2) . . ?
C7 S2 C4 92.6(3) . . ?
C14 O1 C10 122.8(6) . . ?
C1 N1 S1 106.5(4) . . ?
C2 N2 S1 107.5(4) . . ?
N1 C1 C3 123.5(5) . . ?
N1 C1 C2 112.5(5) . . ?
C3 C1 C2 124.1(5) . . ?
N2 C2 C3 124.7(5) . 2_576 ?
N2 C2 C1 111.3(5) . . ?
C3 C2 C1 124.0(5) 2_576 . ?
C1 C3 C2 111.9(5) . 2_576 ?
C1 C3 C4 125.0(5) . . ?
C2 C3 C4 123.1(5) 2_576 . ?
C5 C4 C3 128.3(5) . . ?
C5 C4 S2 108.9(4) . . ?
C3 C4 S2 122.7(4) . . ?
C4 C5 C6 113.9(5) . . ?
C4 C5 H5 123.0 . . ?
C6 C5 H5 123.0 . . ?
C7 C6 C5 113.6(5) . . ?
C7 C6 H6 123.2 . . ?
C5 C6 H6 123.2 . . ?
C6 C7 C8 128.9(5) . . ?
C6 C7 S2 110.8(4) . . ?
C8 C7 S2 120.2(4) . . ?
C13 C8 C9 118.9(6) . . ?
C13 C8 C7 122.2(5) . . ?
C9 C8 C7 118.9(5) . . ?
C8 C9 C10 119.2(6) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 122.5(6) . . ?
C11 C10 O1 114.6(6) . . ?
C9 C10 O1 122.8(6) . . ?
C10 C11 C12 117.4(6) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 121.6(6) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 120.3(6) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
F3 C14 O1 113.2(7) . . ?
F3 C14 F2 104.4(7) . . ?
O1 C14 F2 110.0(8) . . ?
F3 C14 F1 112.3(8) . . ?
O1 C14 F1 117.4(8) . . ?
F2 C14 F1 97.6(7) . . ?

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
N2 S1 N1 C1 0.4(4) . . . . ?
N1 S1 N2 C2 -0.7(4) . . . . ?
S1 N1 C1 C3 179.8(4) . . . . ?
S1 N1 C1 C2 0.1(5) . . . . ?
S1 N2 C2 C3 -179.3(4) . . . 2_576 ?
S1 N2 C2 C1 0.8(5) . . . . ?
N1 C1 C2 N2 -0.6(6) . . . . ?
C3 C1 C2 N2 179.7(5) . . . . ?
N1 C1 C2 C3 179.5(5) . . . 2_576 ?
C3 C1 C2 C3 -0.2(9) . . . 2_576 ?
N1 C1 C3 C2 -179.5(5) . . . 2_576 ?
C2 C1 C3 C2 0.2(8) . . . 2_576 ?
N1 C1 C3 C4 -0.3(8) . . . . ?
C2 C1 C3 C4 179.4(5) . . . . ?
C1 C3 C4 C5 -175.4(6) . . . . ?
C2 C3 C4 C5 3.7(9) 2_576 . . . ?
C1 C3 C4 S2 2.2(8) . . . . ?
C2 C3 C4 S2 -178.6(4) 2_576 . . . ?
C7 S2 C4 C5 -0.3(5) . . . . ?
C7 S2 C4 C3 -178.4(5) . . . . ?
C3 C4 C5 C6 178.1(6) . . . . ?
S2 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C5 C6 C7 C8 -178.7(6) . . . . ?
C5 C6 C7 S2 -0.4(7) . . . . ?
C4 S2 C7 C6 0.4(5) . . . . ?
C4 S2 C7 C8 178.9(5) . . . . ?
C6 C7 C8 C13 -173.1(7) . . . . ?
S2 C7 C8 C13 8.7(8) . . . . ?
C6 C7 C8 C9 5.9(10) . . . . ?
S2 C7 C8 C9 -172.4(5) . . . . ?
C13 C8 C9 C10 -2.8(10) . . . . ?
C7 C8 C9 C10 178.2(6) . . . . ?
C8 C9 C10 C11 2.3(12) . . . . ?
C8 C9 C10 O1 177.9(7) . . . . ?
C14 O1 C10 C11 -135.7(9) . . . . ?
C14 O1 C10 C9 48.3(13) . . . . ?
C9 C10 C11 C12 -0.7(12) . . . . ?
O1 C10 C11 C12 -176.7(7) . . . . ?
C10 C11 C12 C13 -0.2(12) . . . . ?
C11 C12 C13 C8 -0.4(12) . . . . ?
C9 C8 C13 C12 2.0(11) . . . . ?
C7 C8 C13 C12 -179.1(7) . . . . ?
C10 O1 C14 F3 167.1(8) . . . . ?
C10 O1 C14 F2 -76.5(11) . . . . ?
C10 O1 C14 F1 33.8(13) . . . . ?

_refine_diff_density_max         0.895
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_6-oOCF3
_database_code_depnum_ccdc_archive 'CCDC 1416204'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
# start Validation Reply Form

_vrf_PLAT340_6-oOCF3             
;

PROBLEM: Low Bond Precision on C-C Bonds .. 0.0110 Ang.

RESPONSE: The struture presents a disorder and poor diffraction data. 
These factors contribute to the increasing of uncertainty on the atom positions. 
;

# end Validation Reply Form
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H12 F6 N4 O2 S4'
_chemical_formula_sum            'C28 H12 F6 N4 O2 S4'
_chemical_formula_weight         678.66

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'
S S 0.1246 0.1234 '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'

_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                   10.999(2)
_cell_length_b                   7.0481(13)
_cell_length_c                   33.510(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.985(10)
_cell_angle_gamma                90
_cell_volume                     2578.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4107
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      30.3

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.451
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            17073
_diffrn_reflns_av_unetI/netI     0.1081
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4782
_reflns_number_gt                3250
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1050P)²+12.0749P] 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         4782
_refine_ls_number_parameters     426
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.2100
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.21740(17) 0.3495(3) 0.07712(6) 0.0203(5) Uani 1 1 d . . . . .
N1 N 0.1320(6) 0.5353(8) 0.07458(19) 0.0180(14) Uani 1 1 d . . . . .
C1 C 0.0625(7) 0.5310(11) 0.0376(2) 0.0183(17) Uani 1 1 d . . . . .
C2 C 0.0866(6) 0.3643(10) 0.0146(2) 0.0151(15) Uani 1 1 d . . . . .
N2 N 0.1754(6) 0.2490(9) 0.03410(19) 0.0199(14) Uani 1 1 d . . . . .
C3 C -0.0247(6) 0.6740(11) 0.0246(2) 0.0168(16) Uani 1 1 d . . . . .
S2 S 0.02019(17) 0.8729(3) 0.09726(6) 0.0191(5) Uani 1 1 d . . . . .
C4 C -0.0444(7) 0.8437(11) 0.0471(2) 0.0185(16) Uani 1 1 d . . . . .
C5 C -0.1153(7) 1.0022(11) 0.0351(2) 0.0176(16) Uani 1 1 d . . . . .
H5 H -0.1606 1.0140 0.0092 0.021 Uiso 1 1 calc R U . . .
C6 C -0.1134(7) 1.1437(11) 0.0650(2) 0.0187(16) Uani 1 1 d . . . . .
H6 H -0.1553 1.2612 0.0608 0.022 Uiso 1 1 calc R U . . .
C7 C -0.0442(6) 1.0949(11) 0.1014(2) 0.0184(17) Uani 1 1 d . . . . .
C8 C -0.0260(7) 1.2148(11) 0.1373(2) 0.0180(16) Uani 1 1 d . . . . .
C9 C 0.0364(7) 1.1599(11) 0.1742(2) 0.0235(18) Uani 1 1 d . . . . .
C10 C 0.0523(8) 1.2766(13) 0.2077(3) 0.030(2) Uani 1 1 d . . . . .
H10 H 0.0949 1.2312 0.2322 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0055(8) 1.4620(12) 0.2054(3) 0.030(2) Uani 1 1 d . . . . .
H11 H 0.0172 1.5451 0.2279 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0590(8) 1.5201(12) 0.1689(2) 0.0256(19) Uani 1 1 d . . . . .
H12 H -0.0925 1.6444 0.1665 0.031 Uiso 1 1 calc R U . . .
C13 C -0.0743(7) 1.3999(12) 0.1366(3) 0.0260(19) Uani 1 1 d . . . . .
H13 H -0.1200 1.4436 0.1125 0.031 Uiso 1 1 calc R U . . .
O1 O 0.0763(5) 0.9678(8) 0.17853(16) 0.0273(14) Uani 1 1 d . . . . .
C14 C 0.2015(8) 0.9384(14) 0.1837(3) 0.036(2) Uani 1 1 d . . . . .
F1 F 0.2578(5) 1.0282(9) 0.15699(17) 0.0463(15) Uani 1 1 d . . . . .
F2 F 0.2191(5) 0.7550(8) 0.1812(2) 0.0586(18) Uani 1 1 d . . . . .
F3 F 0.2550(5) 0.9989(9) 0.21984(16) 0.0476(15) Uani 1 1 d . . . . .
S3 S 0.65181(18) 0.1578(3) -0.07832(6) 0.0218(5) Uani 1 1 d . . . . .
N3 N 0.6458(6) 0.2541(9) -0.0349(2) 0.0209(15) Uani 1 1 d . . . . .
C15 C 0.5732(7) 0.1382(11) -0.0150(2) 0.0161(16) Uani 1 1 d . . . . .
C16 C 0.5293(7) -0.0284(11) -0.0384(2) 0.0182(17) Uani 1 1 d . . . . .
N4 N 0.5700(6) -0.0290(9) -0.07570(18) 0.0187(14) Uani 1 1 d . . . . .
C17 C 0.5427(6) 0.1738(11) 0.0245(2) 0.0177(16) Uani 1 1 d . . . . .
S4 S 0.56321(17) 0.3640(3) 0.09831(6) 0.0195(5) Uani 1 1 d . . . . .
C18 C 0.5824(7) 0.3411(11) 0.0474(2) 0.0171(16) Uani 1 1 d . . . . .
C19 C 0.6405(7) 0.5027(11) 0.0351(2) 0.0196(17) Uani 1 1 d . . . . .
H19 H 0.6607 0.5181 0.0085 0.024 Uiso 1 1 calc R U . . .
C20 C 0.6671(6) 0.6413(11) 0.0650(2) 0.0182(16) Uani 1 1 d . . . . .
H20 H 0.7053 0.7588 0.0604 0.022 Uiso 1 1 calc R U . . .
C21 C 0.6314(7) 0.5887(11) 0.1022(2) 0.0195(17) Uani 1 1 d . . . . .
C22 C 0.6455(7) 0.7013(11) 0.1385(2) 0.0192(17) Uani 1 1 d . . . . .
C23 C 0.6246(7) 0.6333(11) 0.1772(2) 0.0216(17) Uani 1 1 d . . . . .
C24 C 0.6436(7) 0.7450(13) 0.2113(3) 0.029(2) Uani 1 1 d . . . . .
H24 H 0.6280 0.6947 0.2365 0.034 Uiso 1 1 calc R U . . .
C25 C 0.6851(8) 0.9301(12) 0.2090(3) 0.029(2) Uani 1 1 d . . . . .
H25 H 0.6967 1.0072 0.2324 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7093(8) 1.0002(12) 0.1730(3) 0.031(2) Uani 1 1 d . . . . .
H26 H 0.7391 1.1261 0.1715 0.037 Uiso 1 1 calc R U . . .
C27 C 0.6908(7) 0.8897(11) 0.1380(3) 0.0231(18) Uani 1 1 d . . . . .
H27 H 0.7090 0.9423 0.1133 0.028 Uiso 1 1 calc R U . . .
O2 O 0.5917(5) 0.4416(8) 0.17976(17) 0.0296(14) Uani 1 1 d . . . . .
F4 F 0.4621(5) 0.2176(8) 0.18669(18) 0.0471(15) Uani 1 1 d . . . . .
C28A C 0.481(2) 0.400(4) 0.1902(5) 0.040(4) Uani 0.592(13) 1 d D U P A 1
F5A F 0.4629(14) 0.4418(19) 0.2282(4) 0.058(3) Uani 0.592(13) 1 d D U P A 1
F6A F 0.3918(9) 0.4896(15) 0.1665(4) 0.050(3) Uani 0.592(13) 1 d D U P A 1
C28B C 0.497(3) 0.390(5) 0.1986(5) 0.040(5) Uani 0.408(13) 1 d D U P A 2
F5B F 0.5311(18) 0.388(2) 0.2386(4) 0.050(4) Uani 0.408(13) 1 d D U P A 2
F6B F 0.4039(14) 0.513(2) 0.1923(7) 0.058(3) Uani 0.408(13) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.608(6) . ?
S1 N2 1.622(7) . ?
N1 C1 1.375(10) . ?
C1 C3 1.423(11) . ?
C1 C2 1.447(11) . ?
C2 N2 1.374(9) . ?
C2 C3 1.431(10) 3_565 ?
C3 C2 1.430(10) 3_565 ?
C3 C4 1.443(11) . ?
S2 C7 1.730(8) . ?
S2 C4 1.756(8) . ?
C4 C5 1.394(11) . ?
C5 C6 1.413(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.463(11) . ?
C8 C9 1.396(11) . ?
C8 C13 1.407(11) . ?
C9 C10 1.385(12) . ?
C9 O1 1.425(10) . ?
C10 C11 1.403(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(11) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1 C14 1.382(11) . ?
C14 F2 1.312(11) . ?
C14 F1 1.312(11) . ?
C14 F3 1.349(11) . ?
S3 N4 1.602(7) . ?
S3 N3 1.613(7) . ?
N3 C15 1.371(9) . ?
C15 C17 1.429(10) . ?
C15 C16 1.461(11) . ?
C16 N4 1.376(9) . ?
C16 C17 1.409(11) 3_655 ?
C17 C16 1.409(11) 3_655 ?
C17 C18 1.444(11) . ?
S4 C21 1.751(8) . ?
S4 C18 1.753(7) . ?
C18 C19 1.393(11) . ?
C19 C20 1.404(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.403(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.443(11) . ?
C22 C27 1.419(11) . ?
C22 C23 1.428(11) . ?
C23 C24 1.384(11) . ?
C23 O2 1.404(10) . ?
C24 C25 1.387(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.360(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.402(12) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
O2 C28B 1.33(4) . ?
O2 C28A 1.34(3) . ?
F4 C28A 1.31(3) . ?
F4 C28B 1.32(4) . ?
C28A F6A 1.341(14) . ?
C28A F5A 1.346(14) . ?
C28B F6B 1.341(14) . ?
C28B F5B 1.346(14) . ?

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
N1 S1 N2 102.0(3) . . ?
C1 N1 S1 106.7(5) . . ?
N1 C1 C3 122.7(7) . . ?
N1 C1 C2 112.4(7) . . ?
C3 C1 C2 124.9(7) . . ?
N2 C2 C3 123.8(7) . 3_565 ?
N2 C2 C1 113.1(6) . . ?
C3 C2 C1 123.1(7) 3_565 . ?
C2 N2 S1 105.9(5) . . ?
C1 C3 C2 112.0(7) . 3_565 ?
C1 C3 C4 124.5(7) . . ?
C2 C3 C4 123.4(7) 3_565 . ?
C7 S2 C4 93.5(4) . . ?
C5 C4 C3 128.9(7) . . ?
C5 C4 S2 109.3(6) . . ?
C3 C4 S2 121.8(6) . . ?
C4 C5 C6 113.6(7) . . ?
C4 C5 H5 123.2 . . ?
C6 C5 H5 123.2 . . ?
C7 C6 C5 113.9(7) . . ?
C7 C6 H6 123.0 . . ?
C5 C6 H6 123.0 . . ?
C6 C7 C8 125.4(7) . . ?
C6 C7 S2 109.7(6) . . ?
C8 C7 S2 124.9(6) . . ?
C9 C8 C13 114.5(7) . . ?
C9 C8 C7 124.9(7) . . ?
C13 C8 C7 120.6(7) . . ?
C10 C9 C8 123.6(7) . . ?
C10 C9 O1 118.4(7) . . ?
C8 C9 O1 117.7(7) . . ?
C9 C10 C11 120.0(8) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 117.6(8) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C13 C12 C11 120.7(8) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 123.5(8) . . ?
C12 C13 H13 118.2 . . ?
C8 C13 H13 118.2 . . ?
C14 O1 C9 116.4(7) . . ?
F2 C14 F1 110.2(8) . . ?
F2 C14 F3 108.5(8) . . ?
F1 C14 F3 105.6(8) . . ?
F2 C14 O1 107.0(8) . . ?
F1 C14 O1 112.8(8) . . ?
F3 C14 O1 112.7(8) . . ?
N4 S3 N3 102.2(3) . . ?
C15 N3 S3 106.1(5) . . ?
N3 C15 C17 124.2(7) . . ?
N3 C15 C16 113.1(6) . . ?
C17 C15 C16 122.7(7) . . ?
N4 C16 C17 123.8(7) . 3_655 ?
N4 C16 C15 111.5(6) . . ?
C17 C16 C15 124.7(7) 3_655 . ?
C16 N4 S3 107.1(5) . . ?
C16 C17 C15 112.6(7) 3_655 . ?
C16 C17 C18 124.3(7) 3_655 . ?
C15 C17 C18 123.1(7) . . ?
C21 S4 C18 93.2(4) . . ?
C19 C18 C17 129.2(7) . . ?
C19 C18 S4 109.0(6) . . ?
C17 C18 S4 121.8(6) . . ?
C18 C19 C20 114.9(7) . . ?
C18 C19 H19 122.5 . . ?
C20 C19 H19 122.5 . . ?
C21 C20 C19 113.2(7) . . ?
C21 C20 H20 123.4 . . ?
C19 C20 H20 123.4 . . ?
C20 C21 C22 126.2(7) . . ?
C20 C21 S4 109.6(6) . . ?
C22 C21 S4 124.2(6) . . ?
C27 C22 C23 114.9(7) . . ?
C27 C22 C21 120.4(7) . . ?
C23 C22 C21 124.6(7) . . ?
C24 C23 O2 120.7(7) . . ?
C24 C23 C22 122.4(8) . . ?
O2 C23 C22 116.7(7) . . ?
C23 C24 C25 120.4(8) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.5(8) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 121.1(8) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 121.7(8) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C28B O2 C23 120.8(14) . . ?
C28A O2 C23 118.3(12) . . ?
F4 C28A O2 109.2(9) . . ?
F4 C28A F6A 108(2) . . ?
O2 C28A F6A 111.5(19) . . ?
F4 C28A F5A 105(2) . . ?
O2 C28A F5A 116(2) . . ?
F6A C28A F5A 106.1(10) . . ?
F4 C28B O2 108.8(10) . . ?
F4 C28B F6B 111(3) . . ?
O2 C28B F6B 112(3) . . ?
F4 C28B F5B 109(3) . . ?
O2 C28B F5B 110(3) . . ?
F6B C28B F5B 106.1(10) . . ?

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
N2 S1 N1 C1 -0.8(5) . . . . ?
S1 N1 C1 C3 179.9(6) . . . . ?
S1 N1 C1 C2 1.4(7) . . . . ?
N1 C1 C2 N2 -1.5(9) . . . . ?
C3 C1 C2 N2 180.0(7) . . . . ?
N1 C1 C2 C3 179.1(7) . . . 3_565 ?
C3 C1 C2 C3 0.7(12) . . . 3_565 ?
C3 C2 N2 S1 -179.8(6) 3_565 . . . ?
C1 C2 N2 S1 0.9(7) . . . . ?
N1 S1 N2 C2 -0.1(5) . . . . ?
N1 C1 C3 C2 -178.9(7) . . . 3_565 ?
C2 C1 C3 C2 -0.6(11) . . . 3_565 ?
N1 C1 C3 C4 4.4(11) . . . . ?
C2 C1 C3 C4 -177.3(7) . . . . ?
C1 C3 C4 C5 171.0(7) . . . . ?
C2 C3 C4 C5 -5.3(12) 3_565 . . . ?
C1 C3 C4 S2 -11.0(10) . . . . ?
C2 C3 C4 S2 172.7(6) 3_565 . . . ?
C7 S2 C4 C5 -1.2(6) . . . . ?
C7 S2 C4 C3 -179.5(6) . . . . ?
C3 C4 C5 C6 -179.8(7) . . . . ?
S2 C4 C5 C6 2.0(8) . . . . ?
C4 C5 C6 C7 -2.0(10) . . . . ?
C5 C6 C7 C8 179.6(7) . . . . ?
C5 C6 C7 S2 1.1(8) . . . . ?
C4 S2 C7 C6 0.1(6) . . . . ?
C4 S2 C7 C8 -178.5(7) . . . . ?
C6 C7 C8 C9 175.5(7) . . . . ?
S2 C7 C8 C9 -6.2(11) . . . . ?
C6 C7 C8 C13 -3.5(11) . . . . ?
S2 C7 C8 C13 174.8(6) . . . . ?
C13 C8 C9 C10 -1.0(12) . . . . ?
C7 C8 C9 C10 180.0(8) . . . . ?
C13 C8 C9 O1 173.3(7) . . . . ?
C7 C8 C9 O1 -5.7(11) . . . . ?
C8 C9 C10 C11 -0.7(13) . . . . ?
O1 C9 C10 C11 -174.9(7) . . . . ?
C9 C10 C11 C12 1.5(13) . . . . ?
C10 C11 C12 C13 -0.6(13) . . . . ?
C11 C12 C13 C8 -1.2(13) . . . . ?
C9 C8 C13 C12 2.0(12) . . . . ?
C7 C8 C13 C12 -179.0(7) . . . . ?
C10 C9 O1 C14 -71.5(10) . . . . ?
C8 C9 O1 C14 113.9(8) . . . . ?
C9 O1 C14 F2 -171.0(7) . . . . ?
C9 O1 C14 F1 -49.7(10) . . . . ?
C9 O1 C14 F3 69.8(10) . . . . ?
N4 S3 N3 C15 -0.8(6) . . . . ?
S3 N3 C15 C17 -179.1(6) . . . . ?
S3 N3 C15 C16 1.0(8) . . . . ?
N3 C15 C16 N4 -0.9(9) . . . . ?
C17 C15 C16 N4 179.2(7) . . . . ?
N3 C15 C16 C17 177.4(7) . . . 3_655 ?
C17 C15 C16 C17 -2.4(13) . . . 3_655 ?
C17 C16 N4 S3 -178.1(6) 3_655 . . . ?
C15 C16 N4 S3 0.3(7) . . . . ?
N3 S3 N4 C16 0.3(6) . . . . ?
N3 C15 C17 C16 -177.7(7) . . . 3_655 ?
C16 C15 C17 C16 2.2(11) . . . 3_655 ?
N3 C15 C17 C18 2.2(12) . . . . ?
C16 C15 C17 C18 -177.9(7) . . . . ?
C16 C17 C18 C19 -171.5(7) 3_655 . . . ?
C15 C17 C18 C19 8.6(13) . . . . ?
C16 C17 C18 S4 9.6(11) 3_655 . . . ?
C15 C17 C18 S4 -170.3(6) . . . . ?
C21 S4 C18 C19 0.6(6) . . . . ?
C21 S4 C18 C17 179.6(6) . . . . ?
C17 C18 C19 C20 -180.0(7) . . . . ?
S4 C18 C19 C20 -1.0(8) . . . . ?
C18 C19 C20 C21 1.0(10) . . . . ?
C19 C20 C21 C22 -179.5(7) . . . . ?
C19 C20 C21 S4 -0.5(8) . . . . ?
C18 S4 C21 C20 0.0(6) . . . . ?
C18 S4 C21 C22 178.9(7) . . . . ?
C20 C21 C22 C27 5.1(12) . . . . ?
S4 C21 C22 C27 -173.7(6) . . . . ?
C20 C21 C22 C23 -170.5(7) . . . . ?
S4 C21 C22 C23 10.7(11) . . . . ?
C27 C22 C23 C24 1.9(11) . . . . ?
C21 C22 C23 C24 177.7(8) . . . . ?
C27 C22 C23 O2 -173.7(7) . . . . ?
C21 C22 C23 O2 2.0(11) . . . . ?
O2 C23 C24 C25 175.0(8) . . . . ?
C22 C23 C24 C25 -0.5(13) . . . . ?
C23 C24 C25 C26 -1.1(13) . . . . ?
C24 C25 C26 C27 1.1(14) . . . . ?
C25 C26 C27 C22 0.5(13) . . . . ?
C23 C22 C27 C26 -1.9(11) . . . . ?
C21 C22 C27 C26 -177.9(7) . . . . ?
C24 C23 O2 C28B 52.2(14) . . . . ?
C22 C23 O2 C28B -132.0(12) . . . . ?
C24 C23 O2 C28A 68.0(12) . . . . ?
C22 C23 O2 C28A -116.3(10) . . . . ?
C23 O2 C28A F4 173.2(8) . . . . ?
C23 O2 C28A F6A 53.6(18) . . . . ?
C23 O2 C28A F5A -68.3(18) . . . . ?
C23 O2 C28B F4 161.1(9) . . . . ?
C23 O2 C28B F6B 38(2) . . . . ?
C23 O2 C28B F5B -80(2) . . . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.128

