# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_10F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H26 F4 N8 O4'
_chemical_formula_weight         806.73

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1726(5)
_cell_length_b                   10.6903(6)
_cell_length_c                   10.7126(6)
_cell_angle_alpha                73.150(5)
_cell_angle_beta                 80.841(5)
_cell_angle_gamma                64.809(5)
_cell_volume                     908.96(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3041
_cell_measurement_theta_min      4.3124
_cell_measurement_theta_max      73.8856

_exptl_crystal_description       Shard
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_size_max          0.3486
_exptl_crystal_size_mid          0.2529
_exptl_crystal_size_min          0.1461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6278
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         74.05
_reflns_number_total             3546
_reflns_number_gt                3124
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0513P)²+0.2882P] 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         3546
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
F2 F 0.31529(11) 0.86313(11) 0.93639(9) 0.0434(3) Uani 1 1 d . . .
F1 F -0.10990(12) 0.99022(11) 1.25021(9) 0.0450(3) Uani 1 1 d . . .
N4 N 0.51824(17) 0.82369(16) 1.17856(15) 0.0417(3) Uani 1 1 d . . .
C23 C 0.11424(18) 0.91780(15) 1.10421(14) 0.0270(3) Uani 1 1 d . . .
C21 C 0.38854(19) 0.82776(16) 1.19039(15) 0.0310(3) Uani 1 1 d . . .
N3 N 0.13816(18) 0.74742(19) 1.44285(15) 0.0487(4) Uani 1 1 d . . .
C22 C 0.22813(18) 0.83990(16) 1.20886(14) 0.0290(3) Uani 1 1 d . . .
C25 C 0.15914(17) 0.93139(16) 0.97196(15) 0.0294(3) Uani 1 1 d . . .
C24 C -0.05129(18) 0.99040(16) 1.12579(14) 0.0296(3) Uani 1 1 d . . .
C20 C 0.17818(18) 0.78852(17) 1.33655(16) 0.0335(3) Uani 1 1 d . . .
O1 O 0.36918(15) 0.46800(12) 0.60205(11) 0.0386(3) Uani 1 1 d . . .
O2 O 0.14085(15) 0.44723(14) 0.62855(13) 0.0465(3) Uani 1 1 d . . .
N1 N 0.27889(16) 0.41842(14) 0.58226(13) 0.0328(3) Uani 1 1 d . . .
N2 N 0.11508(16) 0.19620(13) 0.23228(12) 0.0299(3) Uani 1 1 d . . .
C2 C 0.50070(18) 0.27894(17) 0.45353(15) 0.0314(3) Uani 1 1 d . . .
H2 H 0.5670 0.3179 0.4741 0.038 Uiso 1 1 calc R . .
C1 C 0.34139(18) 0.31829(15) 0.49833(14) 0.0284(3) Uani 1 1 d . . .
C14 C -0.11492(19) 0.36782(16) 0.11300(15) 0.0299(3) Uani 1 1 d . . .
C5 C 0.30177(18) 0.16852(15) 0.39237(14) 0.0294(3) Uani 1 1 d . . .
C6 C 0.23952(18) 0.26610(16) 0.46938(14) 0.0286(3) Uani 1 1 d . . .
H6 H 0.1304 0.2960 0.5011 0.034 Uiso 1 1 calc R . .
C12 C -0.3476(2) 0.54213(18) -0.00581(18) 0.0390(4) Uani 1 1 d . . .
H12 H -0.4550 0.6124 -0.0079 0.047 Uiso 1 1 calc R . .
C3 C 0.56062(19) 0.18104(18) 0.37774(16) 0.0352(3) Uani 1 1 d . . .
H3 H 0.6696 0.1520 0.3456 0.042 Uiso 1 1 calc R . .
C9 C -0.02597(19) 0.34454(16) -0.00549(15) 0.0305(3) Uani 1 1 d . . .
C15 C -0.03757(19) 0.28861(16) 0.23148(15) 0.0305(3) Uani 1 1 d . . .
H15 H -0.0955 0.3015 0.3118 0.037 Uiso 1 1 calc R . .
C10 C -0.1062(2) 0.41947(18) -0.12453(16) 0.0364(4) Uani 1 1 d . . .
H10 H -0.0506 0.4033 -0.2049 0.044 Uiso 1 1 calc R . .
C4 C 0.46247(19) 0.12513(17) 0.34841(16) 0.0343(3) Uani 1 1 d . . .
H4 H 0.5054 0.0566 0.2978 0.041 Uiso 1 1 calc R . .
C7 C 0.1932(2) 0.10991(17) 0.35917(16) 0.0339(3) Uani 1 1 d . . .
H7A H 0.2573 0.0099 0.3540 0.041 Uiso 1 1 calc R . .
H7B H 0.1088 0.1101 0.4294 0.041 Uiso 1 1 calc R . .
C13 C -0.2767(2) 0.46876(17) 0.11087(16) 0.0351(3) Uani 1 1 d . . .
H13 H -0.3354 0.4853 0.1901 0.042 Uiso 1 1 calc R . .
C35 C 0.2050(2) 0.17755(17) 0.11835(16) 0.0333(3) Uani 1 1 d . . .
H35 H 0.3155 0.1137 0.1220 0.040 Uiso 1 1 calc R . .
C11 C -0.2626(2) 0.51446(18) -0.12352(17) 0.0392(4) Uani 1 1 d . . .
H11 H -0.3157 0.5631 -0.2036 0.047 Uiso 1 1 calc R . .
C8 C 0.1379(2) 0.24916(17) 0.00105(16) 0.0337(3) Uani 1 1 d . . .
H8 H 0.2012 0.2352 -0.0770 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C25 1.3517(17) . ?
F1 C24 1.3553(17) . ?
N4 C21 1.159(2) . ?
C23 C25 1.394(2) . ?
C23 C24 1.397(2) . ?
C23 C22 1.460(2) . ?
C21 C22 1.407(2) . ?
N3 C20 1.157(2) . ?
C22 C20 1.401(2) . ?
C25 C24 1.376(2) 2_577 ?
C24 C25 1.376(2) 2_577 ?
O1 N1 1.2274(17) . ?
O2 N1 1.2250(17) . ?
N1 C1 1.4677(19) . ?
N2 C15 1.326(2) . ?
N2 C35 1.375(2) . ?
N2 C7 1.494(2) . ?
C2 C1 1.383(2) . ?
C2 C3 1.385(2) . ?
C1 C6 1.385(2) . ?
C14 C15 1.408(2) . ?
C14 C13 1.414(2) . ?
C14 C9 1.421(2) . ?
C5 C4 1.390(2) . ?
C5 C6 1.392(2) . ?
C5 C7 1.512(2) . ?
C12 C13 1.363(2) . ?
C12 C11 1.411(3) . ?
C3 C4 1.387(2) . ?
C9 C8 1.411(2) . ?
C9 C10 1.419(2) . ?
C10 C11 1.361(3) . ?
C35 C8 1.353(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 C23 C24 112.64(13) . . ?
C25 C23 C22 123.82(14) . . ?
C24 C23 C22 123.52(13) . . ?
N4 C21 C22 176.27(17) . . ?
C20 C22 C21 116.43(13) . . ?
C20 C22 C23 121.45(13) . . ?
C21 C22 C23 121.68(13) . . ?
F2 C25 C24 117.57(13) . 2_577 ?
F2 C25 C23 119.22(13) . . ?
C24 C25 C23 123.20(14) 2_577 . ?
F1 C24 C25 117.22(13) . 2_577 ?
F1 C24 C23 118.54(13) . . ?
C25 C24 C23 124.16(14) 2_577 . ?
N3 C20 C22 178.73(17) . . ?
O2 N1 O1 123.95(13) . . ?
O2 N1 C1 118.47(13) . . ?
O1 N1 C1 117.58(13) . . ?
C15 N2 C35 121.56(14) . . ?
C15 N2 C7 119.89(13) . . ?
C35 N2 C7 118.55(13) . . ?
C1 C2 C3 117.94(14) . . ?
C2 C1 C6 123.14(14) . . ?
C2 C1 N1 118.12(13) . . ?
C6 C1 N1 118.74(13) . . ?
C15 C14 C13 121.29(14) . . ?
C15 C14 C9 118.31(14) . . ?
C13 C14 C9 120.39(14) . . ?
C4 C5 C6 119.87(14) . . ?
C4 C5 C7 120.99(14) . . ?
C6 C5 C7 119.13(14) . . ?
C1 C6 C5 118.03(14) . . ?
C13 C12 C11 120.47(16) . . ?
C2 C3 C4 120.40(14) . . ?
C8 C9 C10 123.33(14) . . ?
C8 C9 C14 118.38(14) . . ?
C10 C9 C14 118.28(15) . . ?
N2 C15 C14 120.80(14) . . ?
C11 C10 C9 119.99(15) . . ?
C3 C4 C5 120.60(14) . . ?
N2 C7 C5 111.47(12) . . ?
C12 C13 C14 119.45(15) . . ?
C8 C35 N2 120.72(15) . . ?
C10 C11 C12 121.29(16) . . ?
C35 C8 C9 120.10(15) . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        74.05
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 985158'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_11F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 F4 N8 O4'
_chemical_formula_weight         660.59

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'
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   10.2589(2)
_cell_length_b                   12.2242(2)
_cell_length_c                   22.2473(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.290(2)
_cell_angle_gamma                90.00
_cell_volume                     2778.08(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2508
_cell_measurement_theta_min      3.9878
_cell_measurement_theta_max      73.6961

_exptl_crystal_description       Plate
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.3597
_exptl_crystal_size_mid          0.2354
_exptl_crystal_size_min          0.0381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4971
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         69.99
_reflns_number_total             2633
_reflns_number_gt                2305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0709P)²+1.7985P] 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         2633
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C14 C -0.00018(16) -0.17637(14) 0.18918(7) 0.0201(4) Uani 1 1 d . . .
H14A H 0.0224 -0.2548 0.1941 0.024 Uiso 1 1 calc R . .
H14B H -0.0068 -0.1587 0.1456 0.024 Uiso 1 1 calc R . .
C15 C 0.13081(16) -0.15346(15) 0.28533(7) 0.0203(4) Uani 1 1 d . . .
H15A H 0.1823 -0.1005 0.3115 0.024 Uiso 1 1 calc R . .
H15B H 0.1819 -0.2220 0.2841 0.024 Uiso 1 1 calc R . .
C16 C 0.05303(16) 0.00757(14) 0.22772(7) 0.0197(4) Uani 1 1 d . . .
H16A H 0.0155 0.0337 0.1877 0.024 Uiso 1 1 calc R . .
H16B H 0.1252 0.0573 0.2423 0.024 Uiso 1 1 calc R . .
C12 C 0.23178(16) -0.11011(15) 0.19172(8) 0.0228(4) Uani 1 1 d . . .
H12A H 0.2990 -0.0665 0.2159 0.027 Uiso 1 1 calc R . .
H12B H 0.2634 -0.1866 0.1909 0.027 Uiso 1 1 calc R . .
F2 F 0.02478(11) 0.28728(9) 0.03175(5) 0.0296(3) Uani 1 1 d . . .
F1 F 0.01520(11) 0.66223(9) 0.08244(5) 0.0297(3) Uani 1 1 d . . .
O2 O 0.13449(16) -0.01558(14) -0.09124(6) 0.0406(4) Uani 1 1 d . . .
O1 O 0.17768(14) 0.14821(12) -0.06002(6) 0.0346(4) Uani 1 1 d . . .
C3 C 0.02580(15) 0.47211(14) 0.06413(8) 0.0211(4) Uani 1 1 d . . .
N4 N 0.10450(13) -0.10723(12) 0.22247(6) 0.0182(3) Uani 1 1 d . . .
N1 N 0.14543(17) 0.58365(14) 0.20687(8) 0.0343(4) Uani 1 1 d . . .
C4 C 0.05369(17) 0.44541(15) 0.12785(8) 0.0237(4) Uani 1 1 d . . .
C7 C 0.18317(16) 0.00941(16) 0.01162(8) 0.0227(4) Uani 1 1 d . . .
C9 C 0.19792(18) -0.13961(16) 0.07996(8) 0.0258(4) Uani 1 1 d . . .
H9 H 0.1978 -0.2161 0.0875 0.031 Uiso 1 1 calc R . .
C10 C 0.20564(17) 0.08461(15) 0.05799(8) 0.0242(4) Uani 1 1 d . . .
H10 H 0.2094 0.1608 0.0499 0.029 Uiso 1 1 calc R . .
N3 N 0.16388(14) 0.05041(14) -0.05086(7) 0.0267(4) Uani 1 1 d . . .
C2 C 0.01106(16) 0.57891(15) 0.04237(8) 0.0219(4) Uani 1 1 d . . .
C1 C 0.01215(16) 0.39456(14) 0.01787(8) 0.0215(4) Uani 1 1 d . . .
C5 C 0.10262(18) 0.52448(16) 0.17055(8) 0.0267(4) Uani 1 1 d . . .
C13 C 0.21657(16) -0.06627(15) 0.12828(8) 0.0209(4) Uani 1 1 d . . .
C11 C 0.22252(17) 0.04512(16) 0.11677(8) 0.0240(4) Uani 1 1 d . . .
H11 H 0.2383 0.0949 0.1494 0.029 Uiso 1 1 calc R . .
N2 N 0.0289(2) 0.25392(16) 0.17237(9) 0.0423(5) Uani 1 1 d . . .
C8 C 0.17965(17) -0.10152(16) 0.02121(8) 0.0259(4) Uani 1 1 d . . .
H8 H 0.1650 -0.1509 -0.0117 0.031 Uiso 1 1 calc R . .
C6 C 0.03902(18) 0.33930(16) 0.15093(9) 0.0282(4) 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
C14 N4 1.507(2) . ?
C14 C15 1.528(2) 2 ?
C15 N4 1.509(2) . ?
C15 C14 1.528(2) 2 ?
C16 N4 1.508(2) . ?
C16 C16 1.538(3) 2 ?
C12 C13 1.504(2) . ?
C12 N4 1.529(2) . ?
F2 C1 1.351(2) . ?
F1 C2 1.352(2) . ?
O2 N3 1.224(2) . ?
O1 N3 1.223(2) . ?
C3 C2 1.396(3) . ?
C3 C1 1.397(3) . ?
C3 C4 1.457(2) . ?
N1 C5 1.142(3) . ?
C4 C6 1.408(3) . ?
C4 C5 1.414(3) . ?
C7 C8 1.374(3) . ?
C7 C10 1.385(3) . ?
C7 N3 1.474(2) . ?
C9 C8 1.384(3) . ?
C9 C13 1.399(3) . ?
C10 C11 1.390(3) . ?
C2 C1 1.378(3) 5_565 ?
C1 C2 1.378(3) 5_565 ?
C13 C11 1.388(3) . ?
N2 C6 1.156(3) . ?

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
N4 C14 C15 108.93(13) . 2 ?
N4 C15 C14 108.93(13) . 2 ?
N4 C16 C16 108.87(8) . 2 ?
C13 C12 N4 113.11(13) . . ?
C2 C3 C1 112.26(16) . . ?
C2 C3 C4 123.52(17) . . ?
C1 C3 C4 124.21(17) . . ?
C14 N4 C16 108.75(12) . . ?
C14 N4 C15 107.70(13) . . ?
C16 N4 C15 108.11(12) . . ?
C14 N4 C12 111.49(13) . . ?
C16 N4 C12 112.06(13) . . ?
C15 N4 C12 108.58(12) . . ?
C6 C4 C5 115.32(16) . . ?
C6 C4 C3 122.90(17) . . ?
C5 C4 C3 121.73(17) . . ?
C8 C7 C10 122.99(17) . . ?
C8 C7 N3 118.62(16) . . ?
C10 C7 N3 118.39(17) . . ?
C8 C9 C13 120.47(18) . . ?
C7 C10 C11 117.90(17) . . ?
O1 N3 O2 123.12(16) . . ?
O1 N3 C7 118.81(16) . . ?
O2 N3 C7 118.07(16) . . ?
F1 C2 C1 117.14(16) . 5_565 ?
F1 C2 C3 118.71(16) . . ?
C1 C2 C3 124.12(17) 5_565 . ?
F2 C1 C2 117.08(16) . 5_565 ?
F2 C1 C3 119.30(16) . . ?
C2 C1 C3 123.61(17) 5_565 . ?
N1 C5 C4 176.16(19) . . ?
C11 C13 C9 119.47(16) . . ?
C11 C13 C12 121.34(16) . . ?
C9 C13 C12 119.18(16) . . ?
C13 C11 C10 120.71(17) . . ?
C7 C8 C9 118.39(17) . . ?
N2 C6 C4 177.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 985159'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_12F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 F2 N4 O2'
_chemical_formula_weight         429.40

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1317(4)
_cell_length_b                   9.0430(5)
_cell_length_c                   15.1631(7)
_cell_angle_alpha                96.300(4)
_cell_angle_beta                 98.584(4)
_cell_angle_gamma                116.492(5)
_cell_volume                     966.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4456
_cell_measurement_theta_min      3.0052
_cell_measurement_theta_max      73.7130

_exptl_crystal_description       'large shard'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.6724
_exptl_crystal_size_mid          0.3612
_exptl_crystal_size_min          0.1971
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             442
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6526
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         73.88
_reflns_number_total             3770
_reflns_number_gt                3493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0430P)²+0.3568P] 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         3770
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
F1 F 0.77107(10) 0.61651(10) 0.40478(5) 0.02454(17) Uani 1 1 d . . .
F2 F 0.13062(10) 0.31386(9) 0.41978(5) 0.02425(17) Uani 1 1 d . . .
O1 O 1.59001(13) 0.87854(12) -0.13849(6) 0.0273(2) Uani 1 1 d . . .
O2 O 1.72453(14) 0.79503(15) -0.03620(7) 0.0359(3) Uani 1 1 d . . .
C24 C 0.44422(16) 0.46175(14) 0.39963(8) 0.0173(2) Uani 1 1 d . . .
N2 N 1.04857(14) 0.72623(13) 0.21063(7) 0.0197(2) Uani 1 1 d . . .
C23 C 0.62974(16) 0.55755(15) 0.44954(8) 0.0184(2) Uani 1 1 d . . .
C28 C 0.20254(17) 0.31272(15) 0.25336(8) 0.0200(2) Uani 1 1 d . . .
N1 N 1.59367(15) 0.81795(14) -0.07024(7) 0.0227(2) Uani 1 1 d . . .
C4 C 1.14305(17) 0.77069(15) -0.01591(8) 0.0204(2) Uani 1 1 d . . .
H4 H 1.0419 0.7915 -0.0392 0.024 Uiso 1 1 calc R . .
N3 N 0.62075(16) 0.54071(15) 0.19716(7) 0.0267(2) Uani 1 1 d . . .
C25 C 0.31771(16) 0.40633(15) 0.45681(8) 0.0180(2) Uani 1 1 d . . .
C12 C 1.24267(17) 0.88387(15) 0.49816(8) 0.0207(2) Uani 1 1 d . . .
C27 C 0.51926(17) 0.48875(15) 0.24520(8) 0.0204(2) Uani 1 1 d . . .
C1 C 1.43787(18) 0.70698(17) 0.05223(8) 0.0237(3) Uani 1 1 d . . .
H1 H 1.5384 0.6848 0.0747 0.028 Uiso 1 1 calc R . .
C6 C 1.43395(17) 0.77381(15) -0.02553(8) 0.0197(2) Uani 1 1 d . . .
C8 C 1.16859(19) 0.94084(16) 0.34217(9) 0.0243(3) Uani 1 1 d . . .
H8 H 1.2069 1.0546 0.3686 0.029 Uiso 1 1 calc R . .
C22 C 0.98267(17) 0.67201(16) 0.11057(8) 0.0222(3) Uani 1 1 d . . .
H22A H 0.9139 0.7320 0.0878 0.027 Uiso 1 1 calc R . .
H22B H 0.8939 0.5497 0.0952 0.027 Uiso 1 1 calc R . .
C5 C 1.28787(17) 0.80391(15) -0.06147(8) 0.0207(2) Uani 1 1 d . . .
H5 H 1.2866 0.8463 -0.1160 0.025 Uiso 1 1 calc R . .
C26 C 0.38943(17) 0.42287(15) 0.30064(8) 0.0191(2) Uani 1 1 d . . .
N4 N 0.04951(16) 0.22302(15) 0.21301(7) 0.0268(2) Uani 1 1 d . . .
C11 C 1.05268(17) 0.61503(16) 0.26214(8) 0.0218(3) Uani 1 1 d . . .
H11 H 1.0103 0.5013 0.2340 0.026 Uiso 1 1 calc R . .
C10 C 1.11736(17) 0.66428(16) 0.35468(8) 0.0215(3) Uani 1 1 d . . .
H10 H 1.1211 0.5846 0.3898 0.026 Uiso 1 1 calc R . .
C3 C 1.14455(17) 0.70726(15) 0.06362(8) 0.0194(2) Uani 1 1 d . . .
C2 C 1.29094(18) 0.67326(17) 0.09638(8) 0.0239(3) Uani 1 1 d . . .
H2 H 1.2902 0.6265 0.1495 0.029 Uiso 1 1 calc R . .
C9 C 1.17802(16) 0.83057(15) 0.39818(8) 0.0201(2) Uani 1 1 d . . .
C7 C 1.10476(18) 0.88710(16) 0.24956(9) 0.0238(3) Uani 1 1 d . . .
H7 H 1.1002 0.9641 0.2126 0.029 Uiso 1 1 calc R . .
C13 C 1.23241(19) 1.02051(16) 0.54455(9) 0.0248(3) Uani 1 1 d . . .
H13 H 1.1872 1.0832 0.5113 0.030 Uiso 1 1 calc R . .
C15 C 1.3533(2) 0.97552(18) 0.68798(9) 0.0285(3) Uani 1 1 d . . .
H15 H 1.3897 1.0060 0.7525 0.034 Uiso 1 1 calc R . .
C14 C 1.2876(2) 1.06570(17) 0.63872(9) 0.0278(3) Uani 1 1 d . . .
H14 H 1.2802 1.1591 0.6695 0.033 Uiso 1 1 calc R . .
C16 C 1.3656(2) 0.84070(19) 0.64278(10) 0.0333(3) Uani 1 1 d . . .
H16 H 1.4112 0.7786 0.6763 0.040 Uiso 1 1 calc R . .
C17 C 1.3117(2) 0.79591(18) 0.54863(9) 0.0294(3) Uani 1 1 d . . .
H17 H 1.3220 0.7039 0.5181 0.035 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.3533(13) . ?
F2 C25 1.3550(14) . ?
O1 N1 1.2256(14) . ?
O2 N1 1.2239(14) . ?
C24 C23 1.3958(17) . ?
C24 C25 1.4010(16) . ?
C24 C26 1.4561(16) . ?
N2 C7 1.3460(17) . ?
N2 C11 1.3479(16) . ?
N2 C22 1.4796(15) . ?
C23 C25 1.3777(17) 2_666 ?
C28 N4 1.1593(17) . ?
C28 C26 1.4083(17) . ?
N1 C6 1.4716(15) . ?
C4 C5 1.3883(17) . ?
C4 C3 1.3918(17) . ?
N3 C27 1.1581(17) . ?
C25 C23 1.3777(17) 2_666 ?
C12 C17 1.3918(18) . ?
C12 C13 1.3955(18) . ?
C12 C9 1.4774(17) . ?
C27 C26 1.4107(17) . ?
C1 C6 1.3851(17) . ?
C1 C2 1.3882(18) . ?
C6 C5 1.3820(17) . ?
C8 C7 1.3729(18) . ?
C8 C9 1.3987(17) . ?
C22 C3 1.5153(16) . ?
C11 C10 1.3702(17) . ?
C10 C9 1.4011(18) . ?
C3 C2 1.3936(17) . ?
C13 C14 1.3872(18) . ?
C15 C14 1.3826(19) . ?
C15 C16 1.383(2) . ?
C16 C17 1.3864(19) . ?

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
C23 C24 C25 111.44(10) . . ?
C23 C24 C26 124.25(11) . . ?
C25 C24 C26 124.31(11) . . ?
C7 N2 C11 120.43(11) . . ?
C7 N2 C22 119.53(10) . . ?
C11 N2 C22 120.04(10) . . ?
F1 C23 C25 116.32(10) . 2_666 ?
F1 C23 C24 119.22(10) . . ?
C25 C23 C24 124.43(11) 2_666 . ?
N4 C28 C26 178.76(13) . . ?
O2 N1 O1 123.60(11) . . ?
O2 N1 C6 118.15(10) . . ?
O1 N1 C6 118.24(10) . . ?
C5 C4 C3 120.66(11) . . ?
F2 C25 C23 116.43(10) . 2_666 ?
F2 C25 C24 119.43(10) . . ?
C23 C25 C24 124.13(11) 2_666 . ?
C17 C12 C13 118.34(12) . . ?
C17 C12 C9 120.47(11) . . ?
C13 C12 C9 121.17(11) . . ?
N3 C27 C26 177.68(13) . . ?
C6 C1 C2 118.20(11) . . ?
C5 C6 C1 122.51(11) . . ?
C5 C6 N1 118.85(11) . . ?
C1 C6 N1 118.63(11) . . ?
C7 C8 C9 120.98(12) . . ?
N2 C22 C3 111.96(10) . . ?
C6 C5 C4 118.40(11) . . ?
C28 C26 C27 115.18(10) . . ?
C28 C26 C24 122.02(11) . . ?
C27 C26 C24 122.79(11) . . ?
N2 C11 C10 120.72(11) . . ?
C11 C10 C9 120.87(11) . . ?
C4 C3 C2 119.43(11) . . ?
C4 C3 C22 118.70(11) . . ?
C2 C3 C22 121.85(11) . . ?
C1 C2 C3 120.75(11) . . ?
C8 C9 C10 116.41(11) . . ?
C8 C9 C12 122.21(11) . . ?
C10 C9 C12 121.35(11) . . ?
N2 C7 C8 120.58(11) . . ?
C14 C13 C12 120.60(12) . . ?
C14 C15 C16 119.62(12) . . ?
C15 C14 C13 120.36(12) . . ?
C15 C16 C17 120.15(13) . . ?
C16 C17 C12 120.93(12) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        73.88
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 985160'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_12TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N4 O2'
_chemical_formula_weight         393.42

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0055(5)
_cell_length_b                   8.5844(5)
_cell_length_c                   15.3367(8)
_cell_angle_alpha                74.027(5)
_cell_angle_beta                 88.077(5)
_cell_angle_gamma                67.144(6)
_cell_volume                     930.52(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2876
_cell_measurement_theta_min      5.7491
_cell_measurement_theta_max      73.6329

_exptl_crystal_description       'Small Rod'
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_size_max          0.2150
_exptl_crystal_size_mid          0.0507
_exptl_crystal_size_min          0.0186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6159
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.75
_diffrn_reflns_theta_max         73.80
_reflns_number_total             3649
_reflns_number_gt                3123
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0526P)²+0.1454P] 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         3649
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0957
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.34247(13) 0.51889(14) 0.21324(7) 0.0221(2) Uani 1 1 d . . .
O1 O 0.75036(13) 1.00062(13) -0.13323(7) 0.0305(2) Uani 1 1 d . . .
N1 N 0.81303(15) 0.87175(15) -0.06679(7) 0.0269(2) Uani 1 1 d . . .
C13 C 0.37756(16) 0.35661(16) 0.50308(9) 0.0225(2) Uani 1 1 d . . .
C7 C 0.32124(17) 0.57196(18) 0.11282(9) 0.0254(3) Uani 1 1 d . . .
H7A H 0.1965 0.6615 0.0921 0.031 Uiso 1 1 calc R . .
H7B H 0.3353 0.4680 0.0924 0.031 Uiso 1 1 calc R . .
C21 C 1.01883(15) -0.05953(15) 0.59769(8) 0.0214(2) Uani 1 1 d . . .
C19 C 0.93658(16) -0.12622(16) 0.54590(9) 0.0225(2) Uani 1 1 d . . .
H19 H 0.8923 -0.2131 0.5763 0.027 Uiso 1 1 calc R . .
N4 N 1.18056(16) 0.01346(16) 0.78819(8) 0.0313(3) Uani 1 1 d . . .
C20 C 1.08197(15) 0.06859(16) 0.54881(8) 0.0220(2) Uani 1 1 d . . .
H20 H 1.1387 0.1170 0.5813 0.026 Uiso 1 1 calc R . .
C5 C 0.39712(16) 0.78088(17) -0.01366(9) 0.0235(3) Uani 1 1 d . . .
H5 H 0.2754 0.8228 -0.0386 0.028 Uiso 1 1 calc R . .
C12 C 0.36695(15) 0.41383(16) 0.40254(9) 0.0219(2) Uani 1 1 d . . .
C23 C 0.96997(16) -0.24359(17) 0.74614(8) 0.0241(3) Uani 1 1 d . . .
O2 O 0.97165(15) 0.80751(18) -0.03561(8) 0.0483(3) Uani 1 1 d . . .
C3 C 0.75512(17) 0.65395(18) 0.05904(9) 0.0270(3) Uani 1 1 d . . .
H3 H 0.8776 0.6109 0.0831 0.032 Uiso 1 1 calc R . .
C2 C 0.51447(17) 0.85419(17) -0.05906(8) 0.0236(3) Uani 1 1 d . . .
H2 H 0.4745 0.9460 -0.1146 0.028 Uiso 1 1 calc R . .
C22 C 1.03686(16) -0.11924(17) 0.69725(9) 0.0233(3) Uani 1 1 d . . .
N3 N 0.91465(16) -0.34716(16) 0.78606(8) 0.0308(3) Uani 1 1 d . . .
C9 C 0.45580(17) 0.35423(17) 0.25940(9) 0.0254(3) Uani 1 1 d . . .
H9 H 0.5261 0.2747 0.2269 0.030 Uiso 1 1 calc R . .
C8 C 0.24034(17) 0.63220(17) 0.25832(9) 0.0261(3) Uani 1 1 d . . .
H8 H 0.1602 0.7476 0.2252 0.031 Uiso 1 1 calc R . .
C6 C 0.45619(16) 0.64684(16) 0.06793(8) 0.0222(2) Uani 1 1 d . . .
C10 C 0.25051(17) 0.58297(17) 0.35189(9) 0.0259(3) Uani 1 1 d . . .
H10 H 0.1774 0.6650 0.3826 0.031 Uiso 1 1 calc R . .
C11 C 0.47086(16) 0.30019(17) 0.35265(9) 0.0250(3) Uani 1 1 d . . .
H11 H 0.5528 0.1842 0.3839 0.030 Uiso 1 1 calc R . .
C4 C 0.63590(17) 0.58225(18) 0.10333(9) 0.0268(3) Uani 1 1 d . . .
H4 H 0.6773 0.4885 0.1581 0.032 Uiso 1 1 calc R . .
C1 C 0.69109(16) 0.78932(17) -0.02090(8) 0.0234(3) Uani 1 1 d . . .
C24 C 1.11479(16) -0.04756(17) 0.74778(8) 0.0239(3) Uani 1 1 d . . .
C18 C 0.39716(19) 0.24818(19) 0.69352(9) 0.0289(3) Uani 1 1 d . . .
H18 H 0.4043 0.2118 0.7581 0.035 Uiso 1 1 calc R . .
C14 C 0.24224(19) 0.45041(18) 0.55078(10) 0.0316(3) Uani 1 1 d . . .
H14 H 0.1420 0.5527 0.5182 0.038 Uiso 1 1 calc R . .
C15 C 0.52249(18) 0.20710(19) 0.55287(10) 0.0318(3) Uani 1 1 d . . .
H15 H 0.6161 0.1412 0.5219 0.038 Uiso 1 1 calc R . .
C17 C 0.5318(2) 0.1532(2) 0.64732(10) 0.0346(3) Uani 1 1 d . . .
H17 H 0.6312 0.0506 0.6803 0.042 Uiso 1 1 calc R . .
C16 C 0.2522(2) 0.3964(2) 0.64506(10) 0.0342(3) Uani 1 1 d . . .
H16 H 0.1588 0.4615 0.6765 0.041 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C8 1.3442(17) . ?
N2 C9 1.3485(17) . ?
N2 C7 1.4763(16) . ?
O1 N1 1.2234(15) . ?
N1 O2 1.2235(16) . ?
N1 C1 1.4715(16) . ?
C13 C15 1.3928(18) . ?
C13 C14 1.3965(18) . ?
C13 C12 1.4784(17) . ?
C7 C6 1.5167(17) . ?
C21 C19 1.4037(18) . ?
C21 C20 1.4070(18) . ?
C21 C22 1.4635(17) . ?
C19 C20 1.3923(18) 2_756 ?
N4 C24 1.1622(18) . ?
C20 C19 1.3923(18) 2_756 ?
C5 C2 1.3920(18) . ?
C5 C6 1.3921(18) . ?
C12 C10 1.3989(18) . ?
C12 C11 1.4024(17) . ?
C23 N3 1.1617(18) . ?
C23 C22 1.4018(18) . ?
C3 C1 1.3827(19) . ?
C3 C4 1.3906(18) . ?
C2 C1 1.3843(18) . ?
C22 C24 1.4004(18) . ?
C9 C11 1.3705(19) . ?
C8 C10 1.3756(19) . ?
C6 C4 1.3925(17) . ?
C18 C16 1.382(2) . ?
C18 C17 1.383(2) . ?
C14 C16 1.386(2) . ?
C15 C17 1.389(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C9 120.26(11) . . ?
C8 N2 C7 119.55(11) . . ?
C9 N2 C7 120.07(11) . . ?
O1 N1 O2 123.79(11) . . ?
O1 N1 C1 118.45(10) . . ?
O2 N1 C1 117.75(11) . . ?
C15 C13 C14 118.14(12) . . ?
C15 C13 C12 120.89(11) . . ?
C14 C13 C12 120.97(11) . . ?
N2 C7 C6 113.91(10) . . ?
C19 C21 C20 116.46(12) . . ?
C19 C21 C22 121.77(11) . . ?
C20 C21 C22 121.77(11) . . ?
C20 C19 C21 121.86(12) 2_756 . ?
C19 C20 C21 121.68(11) 2_756 . ?
C2 C5 C6 120.72(11) . . ?
C10 C12 C11 116.33(12) . . ?
C10 C12 C13 121.93(11) . . ?
C11 C12 C13 121.73(11) . . ?
N3 C23 C22 179.45(14) . . ?
C1 C3 C4 118.40(11) . . ?
C1 C2 C5 118.05(12) . . ?
C24 C22 C23 117.13(11) . . ?
C24 C22 C21 120.92(11) . . ?
C23 C22 C21 121.88(11) . . ?
N2 C9 C11 120.85(11) . . ?
N2 C8 C10 120.76(12) . . ?
C5 C6 C4 119.65(11) . . ?
C5 C6 C7 117.69(11) . . ?
C4 C6 C7 122.61(11) . . ?
C8 C10 C12 120.91(11) . . ?
C9 C11 C12 120.88(12) . . ?
C3 C4 C6 120.46(12) . . ?
C3 C1 C2 122.69(12) . . ?
C3 C1 N1 119.20(11) . . ?
C2 C1 N1 118.10(11) . . ?
N4 C24 C22 178.69(14) . . ?
C16 C18 C17 119.56(13) . . ?
C16 C14 C13 120.91(13) . . ?
C17 C15 C13 120.79(12) . . ?
C18 C17 C15 120.33(13) . . ?
C18 C16 C14 120.27(13) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        73.80
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 985161'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13F4TCNQ

# start Validation Reply Form
_vrf_PLAT353_shelxl              
;
PROBLEM: Long    N-H (N0.87,N1.01A) N3     -   H99    ...       1.24 Ang.  
RESPONSE: The proton in question is located between two chemically equivalent nitrogen atoms in proton sponge. It is normal for the proton to be located in such a site in its cation form.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H38 F4 N8'
_chemical_formula_weight         706.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0730 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6578(7)
_cell_length_b                   9.6463(6)
_cell_length_c                   11.6657(7)
_cell_angle_alpha                109.413(6)
_cell_angle_beta                 101.096(6)
_cell_angle_gamma                92.685(6)
_cell_volume                     895.22(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2008
_cell_measurement_theta_min      4.1163
_cell_measurement_theta_max      73.7029

_exptl_crystal_description       'Large Rod'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             370
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5246
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         64.99
_reflns_number_total             3033
_reflns_number_gt                2524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0708P)²+0.0332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3033
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1244
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C19 C 0.2499(2) 0.5812(2) 0.94556(18) 0.0349(4) Uani 1 1 d . . .
H19A H 0.3469 0.5914 0.9160 0.052 Uiso 1 1 calc R . .
H19B H 0.1908 0.4834 0.8971 0.052 Uiso 1 1 calc R . .
H19C H 0.2777 0.5919 1.0338 0.052 Uiso 1 1 calc R . .
C17 C 0.2192(3) 0.6422(2) 0.64342(17) 0.0382(5) Uani 1 1 d . . .
H17A H 0.2244 0.6747 0.5730 0.057 Uiso 1 1 calc R . .
H17B H 0.1776 0.5370 0.6122 0.057 Uiso 1 1 calc R . .
H17C H 0.3257 0.6567 0.6962 0.057 Uiso 1 1 calc R . .
C20 C 0.0001(2) 0.6847(2) 0.9703(2) 0.0408(5) Uani 1 1 d . . .
H20A H 0.0232 0.6979 1.0592 0.061 Uiso 1 1 calc R . .
H20B H -0.0588 0.5867 0.9221 0.061 Uiso 1 1 calc R . .
H20C H -0.0637 0.7612 0.9563 0.061 Uiso 1 1 calc R . .
C18 C -0.0519(2) 0.7102(2) 0.64274(19) 0.0424(5) Uani 1 1 d . . .
H18A H -0.1156 0.7772 0.6919 0.064 Uiso 1 1 calc R . .
H18B H -0.0986 0.6075 0.6200 0.064 Uiso 1 1 calc R . .
H18C H -0.0498 0.7324 0.5669 0.064 Uiso 1 1 calc R . .
H99 H 0.115(3) 0.693(3) 0.810(3) 0.059(7) Uiso 1 1 d . . .
F2 F 0.18572(12) 0.98439(11) 0.40789(10) 0.0374(3) Uani 1 1 d . . .
F1 F 0.65280(13) 0.75630(11) 0.45917(10) 0.0371(3) Uani 1 1 d . . .
C4 C 0.4100(2) 0.85555(19) 0.42505(14) 0.0265(4) Uani 1 1 d . . .
C5 C 0.5732(2) 0.87576(19) 0.47589(15) 0.0274(4) Uani 1 1 d . . .
C6 C 0.3425(2) 0.98811(19) 0.45406(15) 0.0283(4) Uani 1 1 d . . .
C3 C 0.3218(2) 0.71141(19) 0.34724(15) 0.0296(4) Uani 1 1 d . . .
C1 C 0.3975(2) 0.59737(19) 0.27780(16) 0.0335(4) Uani 1 1 d . . .
N1 N 0.4553(2) 0.50340(19) 0.21593(17) 0.0476(5) Uani 1 1 d . . .
C2 C 0.1576(2) 0.6784(2) 0.33284(16) 0.0332(4) Uani 1 1 d . . .
N2 N 0.0230(2) 0.6433(2) 0.31907(18) 0.0468(4) Uani 1 1 d . . .
N3 N 0.11276(18) 0.73042(17) 0.71774(13) 0.0310(4) Uani 1 1 d . . .
C16 C 0.2398(2) 0.93501(18) 0.91200(15) 0.0259(4) Uani 1 1 d . . .
N4 N 0.15066(17) 0.69721(16) 0.93008(13) 0.0280(3) Uani 1 1 d . . .
C11 C 0.3122(2) 1.08467(19) 0.97168(16) 0.0296(4) Uani 1 1 d . . .
C7 C 0.1788(2) 0.8861(2) 0.78070(16) 0.0293(4) Uani 1 1 d . . .
C14 C 0.2974(2) 0.9024(2) 1.11352(16) 0.0323(4) Uani 1 1 d . . .
H14 H 0.2923 0.8413 1.1623 0.039 Uiso 1 1 calc R . .
C10 C 0.3155(2) 1.1780(2) 0.90025(18) 0.0342(4) Uani 1 1 d . . .
H10 H 0.3641 1.2774 0.9401 0.041 Uiso 1 1 calc R . .
C15 C 0.2336(2) 0.84714(19) 0.98860(15) 0.0270(4) Uani 1 1 d . . .
C8 C 0.1825(2) 0.9803(2) 0.71537(17) 0.0351(4) Uani 1 1 d . . .
H8 H 0.1387 0.9454 0.6282 0.042 Uiso 1 1 calc R . .
C9 C 0.2507(3) 1.1283(2) 0.77615(19) 0.0392(5) Uani 1 1 d . . .
H9 H 0.2514 1.1934 0.7304 0.047 Uiso 1 1 calc R . .
C12 C 0.3761(2) 1.1381(2) 1.10129(17) 0.0332(4) Uani 1 1 d . . .
H12 H 0.4239 1.2378 1.1410 0.040 Uiso 1 1 calc R . .
C13 C 0.3707(2) 1.0493(2) 1.17074(16) 0.0360(4) Uani 1 1 d . . .
H13 H 0.4163 1.0866 1.2576 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C19 N4 1.479(2) . ?
C17 N3 1.489(2) . ?
C20 N4 1.481(3) . ?
C18 N3 1.488(2) . ?
F2 C6 1.355(2) . ?
F1 C5 1.348(2) . ?
C4 C6 1.396(2) . ?
C4 C5 1.401(3) . ?
C4 C3 1.461(2) . ?
C5 C6 1.375(3) 2_676 ?
C6 C5 1.375(3) 2_676 ?
C3 C1 1.405(3) . ?
C3 C2 1.408(3) . ?
C1 N1 1.157(3) . ?
C2 N2 1.163(3) . ?
N3 C7 1.465(2) . ?
C16 C7 1.426(2) . ?
C16 C15 1.428(2) . ?
C16 C11 1.428(2) . ?
N4 C15 1.460(2) . ?
C11 C12 1.411(3) . ?
C11 C10 1.419(3) . ?
C7 C8 1.370(3) . ?
C14 C15 1.364(2) . ?
C14 C13 1.407(3) . ?
C10 C9 1.357(3) . ?
C8 C9 1.405(3) . ?
C12 C13 1.366(3) . ?

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
C6 C4 C5 112.67(15) . . ?
C6 C4 C3 124.06(16) . . ?
C5 C4 C3 123.25(16) . . ?
F1 C5 C6 117.48(15) . 2_676 ?
F1 C5 C4 119.08(15) . . ?
C6 C5 C4 123.41(16) 2_676 . ?
F2 C6 C5 117.45(15) . 2_676 ?
F2 C6 C4 118.60(15) . . ?
C5 C6 C4 123.92(17) 2_676 . ?
C1 C3 C2 115.66(15) . . ?
C1 C3 C4 121.00(17) . . ?
C2 C3 C4 123.31(16) . . ?
N1 C1 C3 177.00(19) . . ?
N2 C2 C3 176.4(2) . . ?
C7 N3 C18 113.34(15) . . ?
C7 N3 C17 112.20(15) . . ?
C18 N3 C17 111.82(15) . . ?
C7 C16 C15 125.39(16) . . ?
C7 C16 C11 117.16(16) . . ?
C15 C16 C11 117.45(15) . . ?
C15 N4 C19 113.76(14) . . ?
C15 N4 C20 111.41(15) . . ?
C19 N4 C20 111.82(15) . . ?
C12 C11 C10 121.08(17) . . ?
C12 C11 C16 119.41(16) . . ?
C10 C11 C16 119.50(16) . . ?
C8 C7 C16 121.47(17) . . ?
C8 C7 N3 121.06(15) . . ?
C16 C7 N3 117.47(15) . . ?
C15 C14 C13 120.45(17) . . ?
C9 C10 C11 121.33(17) . . ?
C14 C15 C16 121.48(16) . . ?
C14 C15 N4 120.54(15) . . ?
C16 C15 N4 117.93(14) . . ?
C7 C8 C9 120.55(17) . . ?
C10 C9 C8 119.91(17) . . ?
C13 C12 C11 121.24(17) . . ?
C12 C13 C14 119.94(16) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        64.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 985162'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H56 F8 N16 O'
_chemical_formula_weight         1181.22

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.9040(10)
_cell_length_b                   13.3891(8)
_cell_length_c                   19.1890(12)
_cell_angle_alpha                76.376(5)
_cell_angle_beta                 75.564(6)
_cell_angle_gamma                65.911(6)
_cell_volume                     2897.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    3716
_cell_measurement_theta_min      3.6553
_cell_measurement_theta_max      72.2144

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_size_max          0.1725
_exptl_crystal_size_mid          0.1166
_exptl_crystal_size_min          0.0504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1228
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19887
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         67.50
_reflns_number_total             10408
_reflns_number_gt                4624
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0861P)²+0.0000P] 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         10408
_refine_ls_number_parameters     777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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
C60 C 0.9791(8) 0.1540(8) 0.5381(5) 0.160(4) Uani 1 1 d . . .
H60 H 0.9810 0.1499 0.4895 0.192 Uiso 1 1 calc R . .
O1 O 0.7186(6) 0.0887(5) 0.8168(3) 0.164(2) Uani 1 1 d . . .
H1 H 0.7403 0.0727 0.8566 0.247 Uiso 1 1 calc R . .
C99 C 0.6794(9) 0.0065(7) 0.8091(5) 0.213(5) Uani 1 1 d . . .
H99A H 0.7441 -0.0634 0.8057 0.320 Uiso 1 1 calc R . .
H99B H 0.6457 0.0296 0.7653 0.320 Uiso 1 1 calc R . .
H99C H 0.6220 -0.0023 0.8510 0.320 Uiso 1 1 calc R . .
F6 F 0.6818(2) 0.96888(19) 0.40004(11) 0.0733(7) Uani 1 1 d . . .
F5 F 0.6331(2) 0.79105(19) 0.45137(11) 0.0760(7) Uani 1 1 d . . .
F8 F 0.5596(2) 0.87000(19) 0.69043(11) 0.0790(7) Uani 1 1 d . . .
F7 F 0.6142(2) 1.0453(2) 0.63864(12) 0.0868(8) Uani 1 1 d . . .
C21 C 0.6550(3) 1.0142(3) 0.51683(19) 0.0555(9) Uani 1 1 d . . .
N9 N 0.7272(3) 0.4702(3) 0.36557(16) 0.0565(8) Uani 1 1 d . . .
C20 C 0.6184(3) 0.9837(3) 0.5898(2) 0.0588(10) Uani 1 1 d . . .
C18 C 0.6289(3) 0.8516(3) 0.50062(19) 0.0559(9) Uani 1 1 d . . .
C16 C 0.5944(3) 0.8206(3) 0.57372(19) 0.0553(9) Uani 1 1 d . . .
C19 C 0.6557(3) 0.9441(3) 0.47356(18) 0.0565(9) Uani 1 1 d . . .
N10 N 0.5822(3) 0.6044(3) 0.28385(18) 0.0651(9) Uani 1 1 d . . .
C17 C 0.5911(3) 0.8922(3) 0.61682(19) 0.0589(10) Uani 1 1 d . . .
N14 N 1.0737(3) 0.0495(3) 0.79127(17) 0.0633(9) Uani 1 1 d . . .
C23 C 0.6432(4) 1.2017(3) 0.5244(2) 0.0693(11) Uani 1 1 d . . .
C22 C 0.6859(3) 1.1112(3) 0.4875(2) 0.0580(10) Uani 1 1 d . . .
C15 C 0.5691(3) 0.7195(3) 0.60377(19) 0.0553(9) Uani 1 1 d . . .
N15 N 1.2243(3) -0.1236(3) 0.84840(16) 0.0594(8) Uani 1 1 d . . .
C14 C 0.6257(4) 0.6254(3) 0.5698(2) 0.0639(10) Uani 1 1 d . . .
C13 C 0.4896(3) 0.7111(3) 0.6660(2) 0.0607(10) Uani 1 1 d . . .
N5 N 0.4243(3) 0.6986(3) 0.7175(2) 0.0807(11) Uani 1 1 d . . .
C24 C 0.7589(4) 1.1226(3) 0.4208(2) 0.0610(10) Uani 1 1 d . . .
N6 N 0.6719(3) 0.5455(3) 0.5437(2) 0.0842(12) Uani 1 1 d . . .
N8 N 0.8184(4) 1.1372(3) 0.3671(2) 0.0850(12) Uani 1 1 d . . .
N7 N 0.6069(4) 1.2804(3) 0.5519(2) 0.0978(14) Uani 1 1 d . . .
C52 C 1.0677(4) 0.0576(3) 0.8684(2) 0.0675(11) Uani 1 1 d . . .
H52A H 0.9889 0.0719 0.8949 0.081 Uiso 1 1 calc R . .
H52B H 1.0891 0.1193 0.8702 0.081 Uiso 1 1 calc R . .
C32 C 0.5263(3) 0.5400(3) 0.3452(2) 0.0610(10) Uani 1 1 d . . .
H32A H 0.5073 0.4891 0.3259 0.073 Uiso 1 1 calc R . .
H32B H 0.4547 0.5908 0.3697 0.073 Uiso 1 1 calc R . .
C37 C 0.8099(3) 0.3889(3) 0.4155(2) 0.0634(10) Uani 1 1 d . . .
H37A H 0.7845 0.4120 0.4637 0.076 Uiso 1 1 calc R . .
H37B H 0.8064 0.3157 0.4209 0.076 Uiso 1 1 calc R . .
C50 C 1.0520(4) -0.0509(3) 0.7891(2) 0.0684(11) Uani 1 1 d . . .
H50A H 1.0482 -0.0532 0.7391 0.082 Uiso 1 1 calc R . .
H50B H 0.9782 -0.0485 0.8199 0.082 Uiso 1 1 calc R . .
C35 C 0.7569(4) 0.4351(3) 0.2927(2) 0.0649(10) Uani 1 1 d . . .
H35A H 0.7461 0.3653 0.2976 0.078 Uiso 1 1 calc R . .
H35B H 0.8381 0.4227 0.2726 0.078 Uiso 1 1 calc R . .
C36 C 0.6818(4) 0.5226(4) 0.2415(2) 0.0721(12) Uani 1 1 d . . .
H36A H 0.7273 0.5611 0.2057 0.086 Uiso 1 1 calc R . .
H36B H 0.6528 0.4877 0.2152 0.086 Uiso 1 1 calc R . .
C48 C 1.3084(4) -0.2308(3) 0.8830(2) 0.0687(11) Uani 1 1 d . . .
H48A H 1.2652 -0.2661 0.9233 0.082 Uiso 1 1 calc R . .
H48B H 1.3473 -0.2813 0.8468 0.082 Uiso 1 1 calc R . .
C53 C 1.2807(4) -0.0582(3) 0.7895(2) 0.0693(11) Uani 1 1 d . . .
H53A H 1.3354 -0.1060 0.7543 0.083 Uiso 1 1 calc R . .
H53B H 1.3237 -0.0302 0.8104 0.083 Uiso 1 1 calc R . .
C31 C 0.6073(3) 0.4750(3) 0.3991(2) 0.0653(11) Uani 1 1 d . . .
H31A H 0.5810 0.5104 0.4429 0.078 Uiso 1 1 calc R . .
H31B H 0.6073 0.3997 0.4134 0.078 Uiso 1 1 calc R . .
C54 C 1.1910(3) 0.0388(4) 0.7507(2) 0.0700(11) Uani 1 1 d . . .
H54A H 1.2034 0.1072 0.7479 0.084 Uiso 1 1 calc R . .
H54B H 1.1987 0.0265 0.7010 0.084 Uiso 1 1 calc R . .
C30 C 0.4955(4) 0.6861(4) 0.2355(3) 0.0848(14) Uani 1 1 d . . .
H30A H 0.5361 0.7222 0.1940 0.102 Uiso 1 1 calc R . .
H30B H 0.4380 0.7436 0.2635 0.102 Uiso 1 1 calc R . .
C55 C 0.9811(4) 0.1546(4) 0.7589(3) 0.0798(13) Uani 1 1 d . . .
H55A H 0.9053 0.1594 0.7876 0.096 Uiso 1 1 calc R . .
H55B H 0.9946 0.2195 0.7636 0.096 Uiso 1 1 calc R . .
N16 N 1.3976(4) -0.2139(4) 0.9111(2) 0.1027(14) Uani 1 1 d . . .
C49 C 1.1491(4) -0.1533(4) 0.8161(3) 0.0811(13) Uani 1 1 d . . .
H49A H 1.1165 -0.2021 0.8528 0.097 Uiso 1 1 calc R . .
H49B H 1.1954 -0.1937 0.7755 0.097 Uiso 1 1 calc R . .
C34 C 0.6299(4) 0.6661(4) 0.3153(3) 0.0792(13) Uani 1 1 d . . .
H34A H 0.5683 0.7126 0.3487 0.095 Uiso 1 1 calc R . .
H34B H 0.6594 0.7145 0.2761 0.095 Uiso 1 1 calc R . .
C51 C 1.1487(4) -0.0486(4) 0.9034(2) 0.0864(15) Uani 1 1 d . . .
H51A H 1.1040 -0.0865 0.9405 0.104 Uiso 1 1 calc R . .
H51B H 1.1970 -0.0322 0.9277 0.104 Uiso 1 1 calc R . .
C33 C 0.7261(4) 0.5857(3) 0.3559(2) 0.0713(12) Uani 1 1 d . . .
H33A H 0.8003 0.5880 0.3284 0.086 Uiso 1 1 calc R . .
H33B H 0.7144 0.6070 0.4036 0.086 Uiso 1 1 calc R . .
N12 N 0.9341(4) 0.3795(4) 0.3884(2) 0.1012(13) Uani 1 1 d . . .
C43 C 1.5045(4) -0.2259(5) 0.8671(3) 0.0938(15) Uani 1 1 d . . .
H43 H 1.5209 -0.2462 0.8207 0.113 Uiso 1 1 calc R . .
N11 N 0.4334(4) 0.6320(4) 0.2069(3) 0.1217(18) Uani 1 1 d . . .
C47 C 1.3758(5) -0.1891(4) 0.9815(3) 0.0873(14) Uani 1 1 d . . .
H47 H 1.3060 -0.1865 1.0126 0.105 Uiso 1 1 calc R . .
C46 C 1.4561(6) -0.1688(5) 1.0051(4) 0.1127(19) Uani 1 1 d . . .
H46 H 1.4408 -0.1491 1.0516 0.135 Uiso 1 1 calc R . .
C38 C 0.9733(5) 0.4500(4) 0.4095(3) 0.0924(16) Uani 1 1 d . . .
H38 H 0.9236 0.5028 0.4397 0.111 Uiso 1 1 calc R . .
N13 N 0.9790(5) 0.1586(4) 0.6791(3) 0.1195(16) Uani 1 1 d . . .
C57 C 1.0462(7) 0.2029(7) 0.5501(4) 0.144(3) Uani 1 1 d . . .
H57 H 1.0903 0.2338 0.5114 0.173 Uiso 1 1 calc R . .
C27 C 0.3154(7) 0.5338(7) 0.1617(5) 0.141(3) Uani 1 1 d . . .
H27 H 0.2763 0.4987 0.1469 0.170 Uiso 1 1 calc R . .
C42 C 1.0093(4) 0.2984(5) 0.3462(3) 0.0936(15) Uani 1 1 d . . .
H42 H 0.9839 0.2497 0.3335 0.112 Uiso 1 1 calc R . .
C56 C 1.0459(5) 0.2046(5) 0.6238(4) 0.122(2) Uani 1 1 d . . .
H56 H 1.0910 0.2369 0.6351 0.146 Uiso 1 1 calc R . .
C58 C 0.9109(7) 0.1112(7) 0.5897(5) 0.142(3) Uani 1 1 d . . .
H58 H 0.8654 0.0805 0.5772 0.171 Uiso 1 1 calc R . .
C25 C 0.4775(5) 0.5882(5) 0.1422(3) 0.1087(19) Uani 1 1 d . . .
H25 H 0.5468 0.5921 0.1135 0.130 Uiso 1 1 calc R . .
C40 C 1.1599(6) 0.3617(7) 0.3419(4) 0.131(3) Uani 1 1 d . . .
H40 H 1.2366 0.3566 0.3251 0.157 Uiso 1 1 calc R . .
C29 C 0.3276(4) 0.6290(4) 0.2490(4) 0.1075(19) Uani 1 1 d . . .
H29 H 0.2972 0.6593 0.2925 0.129 Uiso 1 1 calc R . .
C59 C 0.9088(5) 0.1133(5) 0.6620(4) 0.1128(19) Uani 1 1 d . . .
H59 H 0.8609 0.0847 0.6992 0.135 Uiso 1 1 calc R . .
C28 C 0.2704(6) 0.5808(6) 0.2246(5) 0.132(3) Uani 1 1 d . . .
H28 H 0.1990 0.5797 0.2514 0.159 Uiso 1 1 calc R . .
C39 C 1.0859(6) 0.4396(6) 0.3847(4) 0.122(2) Uani 1 1 d . . .
H39 H 1.1130 0.4871 0.3975 0.146 Uiso 1 1 calc R . .
C26 C 0.4170(7) 0.5385(6) 0.1207(4) 0.132(3) Uani 1 1 d . . .
H26 H 0.4464 0.5076 0.0774 0.159 Uiso 1 1 calc R . .
C44 C 1.5849(6) -0.2081(6) 0.8914(4) 0.124(2) Uani 1 1 d . . .
H44 H 1.6572 -0.2164 0.8619 0.149 Uiso 1 1 calc R . .
C41 C 1.1220(5) 0.2913(6) 0.3235(3) 0.121(2) Uani 1 1 d . . .
H41 H 1.1736 0.2370 0.2949 0.146 Uiso 1 1 calc R . .
C45 C 1.5603(6) -0.1779(6) 0.9595(5) 0.129(2) Uani 1 1 d . . .
H45 H 1.6154 -0.1632 0.9751 0.155 Uiso 1 1 calc R . .
F4 F 0.7279(2) 0.6358(2) 0.08357(13) 0.0954(9) Uani 1 1 d . . .
F3 F 0.7909(3) 0.4533(2) 0.03232(14) 0.1056(10) Uani 1 1 d . . .
F1 F 1.0291(3) 0.5776(2) -0.16704(16) 0.1179(12) Uani 1 1 d . . .
F2 F 0.9620(3) 0.7615(2) -0.11700(17) 0.1276(13) Uani 1 1 d . . .
C10 C 0.9497(3) 0.4022(3) -0.1014(2) 0.0611(10) Uani 1 1 d . . .
C8 C 0.9138(3) 0.5038(3) -0.0715(2) 0.0571(9) Uani 1 1 d . . .
C11 C 0.9177(4) 0.3138(4) -0.0634(2) 0.0708(12) Uani 1 1 d . . .
C4 C 0.8415(3) 0.7096(3) -0.0123(2) 0.0594(10) Uani 1 1 d . . .
C5 C 0.8048(4) 0.6229(3) 0.0204(2) 0.0633(10) Uani 1 1 d . . .
C7 C 0.9515(3) 0.5898(3) -0.1047(2) 0.0680(11) Uani 1 1 d . . .
C3 C 0.8042(3) 0.8125(3) 0.0165(2) 0.0650(11) Uani 1 1 d . . .
C9 C 0.8377(3) 0.5275(3) -0.0070(2) 0.0615(10) Uani 1 1 d . . .
C12 C 1.0186(4) 0.3837(3) -0.1691(2) 0.0698(11) Uani 1 1 d . . .
C6 C 0.9170(4) 0.6854(4) -0.0770(2) 0.0746(13) Uani 1 1 d . . .
C2 C 0.8244(4) 0.9043(4) -0.0270(2) 0.0698(11) Uani 1 1 d . . .
C1 C 0.7433(4) 0.8284(4) 0.0863(3) 0.0741(12) Uani 1 1 d . . .
N4 N 0.8392(4) 0.9826(3) -0.0621(2) 0.0880(12) Uani 1 1 d . . .
N3 N 0.6931(4) 0.8451(4) 0.1444(2) 0.0982(14) Uani 1 1 d . . .
N1 N 0.8935(4) 0.2388(3) -0.0343(2) 0.0965(14) Uani 1 1 d . . .
N2 N 1.0757(4) 0.3621(3) -0.2245(2) 0.0989(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
C60 C58 1.339(10) . ?
C60 C57 1.365(11) . ?
O1 C99 1.434(7) . ?
F6 C19 1.359(4) . ?
F5 C18 1.361(4) . ?
F8 C17 1.365(4) . ?
F7 C20 1.366(4) . ?
C21 C20 1.381(5) . ?
C21 C19 1.388(5) . ?
C21 C22 1.458(5) . ?
N9 C35 1.489(4) . ?
N9 C31 1.501(4) . ?
N9 C33 1.508(4) . ?
N9 C37 1.520(5) . ?
C20 C17 1.362(5) . ?
C18 C19 1.372(5) . ?
C18 C16 1.380(5) . ?
C16 C17 1.389(5) . ?
C16 C15 1.473(5) . ?
N10 C32 1.502(4) . ?
N10 C36 1.503(5) . ?
N10 C34 1.504(5) . ?
N10 C30 1.533(5) . ?
N14 C54 1.485(4) . ?
N14 C52 1.491(5) . ?
N14 C50 1.492(5) . ?
N14 C55 1.542(5) . ?
C23 N7 1.160(5) . ?
C23 C22 1.393(5) . ?
C22 C24 1.405(5) . ?
C15 C13 1.383(5) . ?
C15 C14 1.395(5) . ?
N15 C49 1.488(5) . ?
N15 C53 1.490(4) . ?
N15 C51 1.503(5) . ?
N15 C48 1.523(5) . ?
C14 N6 1.155(5) . ?
C13 N5 1.156(5) . ?
C24 N8 1.150(5) . ?
C52 C51 1.501(6) . ?
C32 C31 1.514(5) . ?
C37 N12 1.518(6) . ?
C50 C49 1.519(6) . ?
C35 C36 1.511(6) . ?
C48 N16 1.498(6) . ?
C53 C54 1.525(6) . ?
C30 N11 1.533(6) . ?
C55 N13 1.527(6) . ?
N16 C43 1.396(6) . ?
N16 C47 1.399(6) . ?
C34 C33 1.517(6) . ?
N12 C42 1.392(6) . ?
N12 C38 1.408(6) . ?
C43 C44 1.358(7) . ?
N11 C25 1.389(7) . ?
N11 C29 1.412(6) . ?
C47 C46 1.370(7) . ?
C46 C45 1.386(8) . ?
C38 C39 1.370(7) . ?
N13 C56 1.385(7) . ?
N13 C59 1.411(7) . ?
C57 C56 1.420(9) . ?
C27 C26 1.368(9) . ?
C27 C28 1.378(10) . ?
C42 C41 1.380(7) . ?
C58 C59 1.387(8) . ?
C25 C26 1.391(8) . ?
C40 C41 1.369(9) . ?
C40 C39 1.369(9) . ?
C29 C28 1.373(8) . ?
C44 C45 1.382(8) . ?
F4 C5 1.357(4) . ?
F3 C9 1.353(4) . ?
F1 C7 1.350(4) . ?
F2 C6 1.362(4) . ?
C10 C12 1.391(5) . ?
C10 C11 1.395(5) . ?
C10 C8 1.455(5) . ?
C8 C9 1.387(5) . ?
C8 C7 1.388(5) . ?
C11 N1 1.149(5) . ?
C4 C5 1.386(5) . ?
C4 C6 1.388(5) . ?
C4 C3 1.456(5) . ?
C5 C9 1.361(5) . ?
C7 C6 1.362(5) . ?
C3 C1 1.388(6) . ?
C3 C2 1.394(6) . ?
C12 N2 1.157(5) . ?
C2 N4 1.164(5) . ?
C1 N3 1.164(5) . ?

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
C58 C60 C57 125.5(10) . . ?
C20 C21 C19 112.4(3) . . ?
C20 C21 C22 124.4(3) . . ?
C19 C21 C22 123.2(3) . . ?
C35 N9 C31 108.5(3) . . ?
C35 N9 C33 108.9(3) . . ?
C31 N9 C33 107.4(3) . . ?
C35 N9 C37 111.3(3) . . ?
C31 N9 C37 108.9(3) . . ?
C33 N9 C37 111.9(3) . . ?
C17 C20 F7 117.4(3) . . ?
C17 C20 C21 124.0(3) . . ?
F7 C20 C21 118.6(3) . . ?
F5 C18 C19 117.0(3) . . ?
F5 C18 C16 119.6(3) . . ?
C19 C18 C16 123.4(3) . . ?
C18 C16 C17 112.8(3) . . ?
C18 C16 C15 124.0(3) . . ?
C17 C16 C15 123.1(3) . . ?
F6 C19 C18 117.5(3) . . ?
F6 C19 C21 118.8(3) . . ?
C18 C19 C21 123.7(3) . . ?
C32 N10 C36 107.7(3) . . ?
C32 N10 C34 108.7(3) . . ?
C36 N10 C34 107.8(3) . . ?
C32 N10 C30 111.0(3) . . ?
C36 N10 C30 111.6(3) . . ?
C34 N10 C30 109.8(3) . . ?
C20 C17 F8 117.8(3) . . ?
C20 C17 C16 123.6(3) . . ?
F8 C17 C16 118.6(3) . . ?
C54 N14 C52 108.6(3) . . ?
C54 N14 C50 109.1(3) . . ?
C52 N14 C50 109.2(3) . . ?
C54 N14 C55 111.2(3) . . ?
C52 N14 C55 108.4(3) . . ?
C50 N14 C55 110.3(3) . . ?
N7 C23 C22 176.7(5) . . ?
C23 C22 C24 114.3(3) . . ?
C23 C22 C21 121.6(3) . . ?
C24 C22 C21 124.1(3) . . ?
C13 C15 C14 116.0(3) . . ?
C13 C15 C16 123.3(3) . . ?
C14 C15 C16 120.8(3) . . ?
C49 N15 C53 107.9(3) . . ?
C49 N15 C51 108.1(3) . . ?
C53 N15 C51 107.1(3) . . ?
C49 N15 C48 107.5(3) . . ?
C53 N15 C48 114.0(3) . . ?
C51 N15 C48 112.1(3) . . ?
N6 C14 C15 177.9(4) . . ?
N5 C13 C15 176.4(4) . . ?
N8 C24 C22 176.3(4) . . ?
N14 C52 C51 109.4(3) . . ?
N10 C32 C31 109.8(3) . . ?
N12 C37 N9 113.8(3) . . ?
N14 C50 C49 109.0(3) . . ?
N9 C35 C36 110.5(3) . . ?
N10 C36 C35 109.9(3) . . ?
N16 C48 N15 113.2(3) . . ?
N15 C53 C54 110.6(3) . . ?
N9 C31 C32 110.0(3) . . ?
N14 C54 C53 109.6(3) . . ?
N10 C30 N11 113.6(4) . . ?
N13 C55 N14 114.1(4) . . ?
C43 N16 C47 119.8(5) . . ?
C43 N16 C48 119.3(4) . . ?
C47 N16 C48 120.8(4) . . ?
N15 C49 C50 111.3(3) . . ?
N10 C34 C33 110.5(3) . . ?
C52 C51 N15 111.6(3) . . ?
N9 C33 C34 109.6(3) . . ?
C42 N12 C38 120.7(5) . . ?
C42 N12 C37 120.1(4) . . ?
C38 N12 C37 119.2(4) . . ?
C44 C43 N16 119.8(6) . . ?
C25 N11 C29 120.7(6) . . ?
C25 N11 C30 122.1(5) . . ?
C29 N11 C30 117.2(6) . . ?
C46 C47 N16 120.0(5) . . ?
C47 C46 C45 118.9(6) . . ?
C39 C38 N12 118.1(6) . . ?
C56 N13 C59 120.0(6) . . ?
C56 N13 C55 121.0(6) . . ?
C59 N13 C55 119.0(5) . . ?
C60 C57 C56 116.6(8) . . ?
C26 C27 C28 119.9(8) . . ?
C41 C42 N12 118.5(6) . . ?
N13 C56 C57 119.8(7) . . ?
C60 C58 C59 118.5(8) . . ?
N11 C25 C26 118.6(6) . . ?
C41 C40 C39 119.8(6) . . ?
C28 C29 N11 118.3(7) . . ?
C58 C59 N13 119.5(7) . . ?
C29 C28 C27 121.4(7) . . ?
C40 C39 C38 121.6(7) . . ?
C27 C26 C25 121.1(8) . . ?
C43 C44 C45 119.9(6) . . ?
C40 C41 C42 121.2(7) . . ?
C44 C45 C46 121.3(6) . . ?
C12 C10 C11 114.2(4) . . ?
C12 C10 C8 123.8(3) . . ?
C11 C10 C8 122.1(3) . . ?
C9 C8 C7 111.5(3) . . ?
C9 C8 C10 124.7(3) . . ?
C7 C8 C10 123.8(3) . . ?
N1 C11 C10 177.5(5) . . ?
C5 C4 C6 110.5(4) . . ?
C5 C4 C3 124.7(4) . . ?
C6 C4 C3 124.7(3) . . ?
F4 C5 C9 117.7(3) . . ?
F4 C5 C4 117.3(3) . . ?
C9 C5 C4 124.9(4) . . ?
F1 C7 C6 117.6(3) . . ?
F1 C7 C8 118.5(3) . . ?
C6 C7 C8 123.8(4) . . ?
C1 C3 C2 115.6(4) . . ?
C1 C3 C4 123.7(4) . . ?
C2 C3 C4 120.7(4) . . ?
F3 C9 C5 116.3(3) . . ?
F3 C9 C8 119.6(3) . . ?
C5 C9 C8 124.1(3) . . ?
N2 C12 C10 175.9(5) . . ?
F2 C6 C7 116.0(4) . . ?
F2 C6 C4 118.8(4) . . ?
C7 C6 C4 125.1(4) . . ?
N4 C2 C3 178.3(5) . . ?
N3 C1 C3 177.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 985163'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 F4 N6'
_chemical_formula_weight         462.41

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   11.3750(3)
_cell_length_b                   7.1927(2)
_cell_length_c                   12.4527(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.830(2)
_cell_angle_gamma                90.00
_cell_volume                     1016.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3635
_cell_measurement_theta_min      3.8916
_cell_measurement_theta_max      75.5529

_exptl_crystal_description       'Flat Rod'
_exptl_crystal_colour            'Dark Green'
_exptl_crystal_size_max          0.3371
_exptl_crystal_size_mid          0.0612
_exptl_crystal_size_min          0.0274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5898
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0168
_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       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.10
_diffrn_reflns_theta_max         67.49
_reflns_number_total             1829
_reflns_number_gt                1694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0520P)²+0.3048P] 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         1829
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.11532(6) -0.01554(12) 0.69718(6) 0.0333(2) Uani 1 1 d . . .
F6 F -0.10718(6) -0.10878(12) 0.67655(6) 0.0337(2) Uani 1 1 d . . .
C1 C -0.44012(10) -0.03369(16) 0.98866(10) 0.0208(3) Uani 1 1 d . . .
N6 N -0.21755(9) -0.16214(14) 0.94806(8) 0.0227(2) Uani 1 1 d . . .
C4 C -0.23927(11) -0.10437(18) 1.04743(10) 0.0245(3) Uani 1 1 d . . .
H4 H -0.1780 -0.1077 1.1031 0.029 Uiso 1 1 calc R . .
C2 C 0.06110(11) -0.00832(17) 0.59721(10) 0.0229(3) Uani 1 1 d . . .
N9 N 0.38994(10) -0.01310(19) 0.67727(9) 0.0358(3) Uani 1 1 d . . .
N10 N 0.35699(10) 0.27692(17) 0.37942(9) 0.0301(3) Uani 1 1 d . . .
C3 C 0.12442(10) 0.05123(16) 0.51114(10) 0.0214(3) Uani 1 1 d . . .
C7 C 0.32424(11) 0.03881(18) 0.60864(10) 0.0255(3) Uani 1 1 d . . .
C5 C -0.09799(10) -0.22372(19) 0.92427(11) 0.0280(3) Uani 1 1 d . . .
H5A H -0.0576 -0.1228 0.8888 0.042 Uiso 1 1 calc R . .
H5B H -0.1039 -0.3323 0.8767 0.042 Uiso 1 1 calc R . .
H5C H -0.0533 -0.2569 0.9915 0.042 Uiso 1 1 calc R . .
C6 C -0.05588(11) -0.05750(17) 0.58627(10) 0.0234(3) Uani 1 1 d . . .
C8 C -0.34897(11) -0.04055(17) 1.06973(10) 0.0240(3) Uani 1 1 d . . .
H8 H -0.3629 -0.0009 1.1405 0.029 Uiso 1 1 calc R . .
C9 C -0.41427(11) -0.09371(17) 0.88609(10) 0.0234(3) Uani 1 1 d . . .
H9 H -0.4735 -0.0907 0.8286 0.028 Uiso 1 1 calc R . .
C10 C 0.30573(10) 0.19605(17) 0.44169(10) 0.0232(3) Uani 1 1 d . . .
C11 C -0.30342(11) -0.15695(17) 0.86825(10) 0.0241(3) Uani 1 1 d . . .
H11 H -0.2870 -0.1978 0.7983 0.029 Uiso 1 1 calc R . .
C12 C 0.24921(10) 0.09805(17) 0.52136(10) 0.0228(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
F1 C2 1.3529(14) . ?
F6 C6 1.3521(15) . ?
C1 C9 1.3981(18) . ?
C1 C8 1.3988(18) . ?
C1 C1 1.490(2) 3_457 ?
N6 C4 1.3438(17) . ?
N6 C11 1.3467(16) . ?
N6 C5 1.4790(15) . ?
C4 C8 1.3752(18) . ?
C2 C6 1.3747(18) . ?
C2 C3 1.3979(18) . ?
N9 C7 1.1589(18) . ?
N10 C10 1.1575(18) . ?
C3 C6 1.3982(17) 3_556 ?
C3 C12 1.4562(17) . ?
C7 C12 1.4026(18) . ?
C6 C3 1.3982(17) 3_556 ?
C9 C11 1.3724(18) . ?
C10 C12 1.4070(18) . ?

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
C9 C1 C8 117.22(11) . . ?
C9 C1 C1 121.61(14) . 3_457 ?
C8 C1 C1 121.17(14) . 3_457 ?
C4 N6 C11 120.14(10) . . ?
C4 N6 C5 120.34(10) . . ?
C11 N6 C5 119.46(10) . . ?
N6 C4 C8 120.95(12) . . ?
F1 C2 C6 117.39(11) . . ?
F1 C2 C3 119.39(11) . . ?
C6 C2 C3 123.21(11) . . ?
C2 C3 C6 112.89(11) . 3_556 ?
C2 C3 C12 123.58(11) . . ?
C6 C3 C12 123.52(11) 3_556 . ?
N9 C7 C12 176.73(13) . . ?
F6 C6 C2 117.16(11) . . ?
F6 C6 C3 118.91(11) . 3_556 ?
C2 C6 C3 123.89(12) . 3_556 ?
C4 C8 C1 120.32(12) . . ?
C11 C9 C1 120.12(11) . . ?
N10 C10 C12 176.75(13) . . ?
N6 C11 C9 121.24(12) . . ?
C7 C12 C10 114.56(11) . . ?
C7 C12 C3 122.45(11) . . ?
C10 C12 C3 122.88(11) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 985164'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H30 F4 N6'
_chemical_formula_weight         766.78

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2739(9)
_cell_length_b                   8.9106(11)
_cell_length_c                   14.8749(18)
_cell_angle_alpha                105.302(10)
_cell_angle_beta                 98.243(10)
_cell_angle_gamma                102.661(10)
_cell_volume                     886.34(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1270
_cell_measurement_theta_min      3.1505
_cell_measurement_theta_max      70.5942

_exptl_crystal_description       Shard
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.1511
_exptl_crystal_size_mid          0.0380
_exptl_crystal_size_min          0.0124
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.4(9)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5084
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0895
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         67.48
_reflns_number_total             3167
_reflns_number_gt                1867
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.1276P] 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         3167
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
F2 F 0.0593(3) 0.4742(3) 0.67845(14) 0.0430(6) Uani 1 1 d . . .
F1 F -0.2049(3) 0.6095(3) 0.62866(15) 0.0452(6) Uani 1 1 d . . .
C23 C -0.1043(5) 0.5589(5) 0.5623(3) 0.0365(8) Uani 1 1 d . . .
C20 C -0.3576(5) 0.6510(4) 0.3497(3) 0.0379(9) Uani 1 1 d . . .
C22 C -0.1474(5) 0.5765(4) 0.4722(2) 0.0357(8) Uani 1 1 d . . .
N3 N -0.4140(5) 0.6582(4) 0.2748(2) 0.0474(8) Uani 1 1 d . . .
N2 N -0.5058(5) 0.7724(4) 0.5515(2) 0.0475(9) Uani 1 1 d . . .
C19 C -0.4095(5) 0.7151(5) 0.5058(3) 0.0388(9) Uani 1 1 d . . .
C24 C 0.0334(5) 0.4856(5) 0.5881(3) 0.0381(9) Uani 1 1 d . . .
C21 C -0.2961(5) 0.6510(4) 0.4438(3) 0.0354(8) Uani 1 1 d . . .
N1 N 0.1542(4) 0.8727(4) 0.2863(2) 0.0377(7) Uani 1 1 d . . .
C16 C 0.0316(5) 0.9757(4) 0.4549(2) 0.0350(8) Uani 1 1 d . . .
C13 C 0.2227(5) 0.8177(4) 0.1962(3) 0.0377(9) Uani 1 1 d . . .
H13 H 0.2801 0.7274 0.2016 0.045 Uiso 1 1 calc R . .
C1 C 0.0528(6) 0.7470(5) 0.1104(3) 0.0390(9) Uani 1 1 d . . .
C5 C -0.1122(6) 0.7352(5) -0.0446(3) 0.0465(10) Uani 1 1 d . . .
H5 H -0.1199 0.7778 -0.0968 0.056 Uiso 1 1 calc R . .
C17 C 0.1844(5) 0.9019(5) 0.4498(3) 0.0393(9) Uani 1 1 d . . .
H17 H 0.2479 0.8858 0.5055 0.047 Uiso 1 1 calc R . .
C15 C -0.0528(5) 0.9975(4) 0.3708(3) 0.0378(9) Uani 1 1 d . . .
H15 H -0.1539 1.0492 0.3709 0.045 Uiso 1 1 calc R . .
C18 C 0.2419(5) 0.8535(5) 0.3665(3) 0.0385(9) Uani 1 1 d . . .
H18 H 0.3461 0.8053 0.3651 0.046 Uiso 1 1 calc R . .
C3 C -0.2418(6) 0.5420(5) 0.0297(3) 0.0475(10) Uani 1 1 d . . .
H3 H -0.3396 0.4509 0.0286 0.057 Uiso 1 1 calc R . .
C7 C 0.3834(6) 0.9502(5) 0.1867(3) 0.0406(9) Uani 1 1 d . . .
C12 C 0.5186(6) 0.9030(5) 0.1354(3) 0.0448(10) Uani 1 1 d . . .
H12 H 0.5123 0.7916 0.1112 0.054 Uiso 1 1 calc R . .
C14 C 0.0084(5) 0.9450(5) 0.2878(3) 0.0398(9) Uani 1 1 d . . .
H14 H -0.0520 0.9594 0.2309 0.048 Uiso 1 1 calc R . .
C8 C 0.3964(6) 1.1132(5) 0.2222(3) 0.0464(10) Uani 1 1 d . . .
H8 H 0.3059 1.1469 0.2575 0.056 Uiso 1 1 calc R . .
C10 C 0.6725(6) 1.1792(5) 0.1549(3) 0.0508(11) Uani 1 1 d . . .
H10 H 0.7708 1.2574 0.1436 0.061 Uiso 1 1 calc R . .
C6 C 0.0402(6) 0.8084(5) 0.0338(3) 0.0449(10) Uani 1 1 d . . .
H6 H 0.1362 0.9008 0.0351 0.054 Uiso 1 1 calc R . .
C2 C -0.0908(6) 0.6135(5) 0.1080(3) 0.0441(10) Uani 1 1 d . . .
H2 H -0.0851 0.5713 0.1604 0.053 Uiso 1 1 calc R . .
C11 C 0.6612(6) 1.0176(6) 0.1199(3) 0.0506(11) Uani 1 1 d . . .
H11 H 0.7524 0.9848 0.0847 0.061 Uiso 1 1 calc R . .
C9 C 0.5413(6) 1.2279(5) 0.2064(3) 0.0507(11) Uani 1 1 d . . .
H9 H 0.5498 1.3396 0.2310 0.061 Uiso 1 1 calc R . .
C4 C -0.2523(6) 0.6013(5) -0.0472(3) 0.0460(10) Uani 1 1 d . . .
H4 H -0.3553 0.5502 -0.1014 0.055 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C24 1.364(4) . ?
F1 C23 1.353(4) . ?
C23 C24 1.374(5) . ?
C23 C22 1.390(5) . ?
C20 N3 1.154(5) . ?
C20 C21 1.407(5) . ?
C22 C24 1.396(5) 2_566 ?
C22 C21 1.456(5) . ?
N2 C19 1.150(5) . ?
C19 C21 1.415(5) . ?
C24 C22 1.396(5) 2_566 ?
N1 C18 1.341(5) . ?
N1 C14 1.356(5) . ?
N1 C13 1.495(4) . ?
C16 C15 1.392(5) . ?
C16 C17 1.412(5) . ?
C16 C16 1.469(7) 2_576 ?
C13 C7 1.520(5) . ?
C13 C1 1.528(5) . ?
C1 C2 1.389(5) . ?
C1 C6 1.388(5) . ?
C5 C4 1.376(5) . ?
C5 C6 1.387(5) . ?
C17 C18 1.356(5) . ?
C15 C14 1.374(5) . ?
C3 C2 1.380(5) . ?
C3 C4 1.379(6) . ?
C7 C8 1.384(5) . ?
C7 C12 1.398(5) . ?
C12 C11 1.379(5) . ?
C8 C9 1.392(6) . ?
C10 C11 1.375(6) . ?
C10 C9 1.378(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
F1 C23 C24 116.5(3) . . ?
F1 C23 C22 120.2(3) . . ?
C24 C23 C22 123.3(3) . . ?
N3 C20 C21 175.7(4) . . ?
C23 C22 C24 112.7(3) . 2_566 ?
C23 C22 C21 123.5(3) . . ?
C24 C22 C21 123.8(3) 2_566 . ?
N2 C19 C21 175.1(4) . . ?
F2 C24 C23 117.3(3) . . ?
F2 C24 C22 118.7(3) . 2_566 ?
C23 C24 C22 124.0(3) . 2_566 ?
C20 C21 C19 112.5(3) . . ?
C20 C21 C22 123.8(3) . . ?
C19 C21 C22 123.3(3) . . ?
C18 N1 C14 120.1(3) . . ?
C18 N1 C13 119.2(3) . . ?
C14 N1 C13 120.6(3) . . ?
C15 C16 C17 116.3(3) . . ?
C15 C16 C16 123.4(4) . 2_576 ?
C17 C16 C16 120.3(4) . 2_576 ?
N1 C13 C7 111.3(3) . . ?
N1 C13 C1 110.6(3) . . ?
C7 C13 C1 114.5(3) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 C13 118.6(3) . . ?
C6 C1 C13 122.4(3) . . ?
C4 C5 C6 120.4(4) . . ?
C18 C17 C16 121.0(4) . . ?
C14 C15 C16 120.8(3) . . ?
N1 C18 C17 121.1(4) . . ?
C2 C3 C4 120.8(4) . . ?
C8 C7 C12 119.0(4) . . ?
C8 C7 C13 123.4(4) . . ?
C12 C7 C13 117.6(4) . . ?
C11 C12 C7 120.1(4) . . ?
N1 C14 C15 120.6(3) . . ?
C7 C8 C9 120.4(4) . . ?
C11 C10 C9 120.1(4) . . ?
C5 C6 C1 120.2(4) . . ?
C3 C2 C1 120.2(4) . . ?
C10 C11 C12 120.5(4) . . ?
C10 C9 C8 119.9(4) . . ?
C5 C4 C3 119.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        67.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 985165'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 F4 N8'
_chemical_formula_weight         604.66

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/m

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

_cell_length_a                   13.4546(11)
_cell_length_b                   11.4276(10)
_cell_length_c                   9.1962(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.490(8)
_cell_angle_gamma                90.00
_cell_volume                     1385.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    922
_cell_measurement_theta_min      4.9033
_cell_measurement_theta_max      73.2239

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.4151
_exptl_crystal_size_mid          0.0523
_exptl_crystal_size_min          0.0441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_temperature      130.00(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2516
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.91
_diffrn_reflns_theta_max         70.00
_reflns_number_total             1376
_reflns_number_gt                1136
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0778P)²+0.9355P] 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         1376
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C8 C 0.04900(15) 0.10155(18) 0.0402(2) 0.0388(5) Uani 1 1 d . . .
C9 C 0.1046(2) 0.0000 0.0834(3) 0.0344(6) Uani 1 2 d S . .
C10 C 0.2116(2) 0.0000 0.1589(3) 0.0367(7) Uani 1 2 d S . .
C11 C 0.26915(15) 0.10294(19) 0.1888(2) 0.0409(5) Uani 1 1 d . . .
N3 N 0.32128(14) 0.18429(18) 0.2153(2) 0.0559(6) Uani 1 1 d . . .
F1 F 0.09209(10) 0.20710(12) 0.07775(19) 0.0632(5) Uani 1 1 d . . .
C1 C 0.46111(19) 0.0000 0.8172(3) 0.0381(7) Uani 1 2 d S . .
H1A H 0.4983 0.0701 0.8621 0.046 Uiso 0.50 1 calc PR . .
H1B H 0.4983 -0.0701 0.8621 0.046 Uiso 0.50 1 calc PR . .
C2 C 0.3534(2) 0.0000 0.8513(3) 0.0390(7) Uani 1 2 d S . .
H2A H 0.3439 -0.0702 0.9101 0.047 Uiso 0.50 1 calc PR . .
H2B H 0.3439 0.0702 0.9101 0.047 Uiso 0.50 1 calc PR . .
C3 C 0.29319(14) 0.10622(17) 0.6190(2) 0.0370(5) Uani 1 1 d . . .
H3A H 0.2819 0.1780 0.6738 0.044 Uiso 1 1 calc R . .
H3B H 0.2448 0.1062 0.5226 0.044 Uiso 1 1 calc R . .
C4 C 0.40312(14) 0.10390(18) 0.5931(2) 0.0371(5) Uani 1 1 d . . .
H4A H 0.4019 0.1056 0.4851 0.045 Uiso 1 1 calc R . .
H4B H 0.4394 0.1746 0.6378 0.045 Uiso 1 1 calc R . .
C5 C 0.17255(18) 0.0000 0.7477(3) 0.0312(6) Uani 1 2 d S . .
H5A H 0.1671 -0.0699 0.8092 0.037 Uiso 0.50 1 calc PR . .
H5B H 0.1671 0.0699 0.8092 0.037 Uiso 0.50 1 calc PR . .
C6 C 0.08447(18) 0.0000 0.6175(3) 0.0311(6) Uani 1 2 d S . .
C7 C 0.04138(13) 0.10508(17) 0.5590(2) 0.0350(5) Uani 1 1 d . . .
H7 H 0.0688 0.1773 0.5999 0.042 Uiso 1 1 calc R . .
N1 N 0.27654(15) 0.0000 0.7071(2) 0.0278(5) Uani 1 2 d S . .
N2 N 0.45758(16) 0.0000 0.6575(2) 0.0339(6) Uani 1 2 d S . .


_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
C8 F1 1.353(2) . ?
C8 C8 1.377(4) 2 ?
C8 C9 1.395(2) . ?
C9 C8 1.395(2) 6 ?
C9 C10 1.468(4) . ?
C10 C11 1.405(3) . ?
C10 C11 1.405(3) 6 ?
C11 N3 1.161(3) . ?
C1 N2 1.460(3) . ?
C1 C2 1.543(4) . ?
C2 N1 1.510(3) . ?
C3 N1 1.501(2) . ?
C3 C4 1.545(3) . ?
C4 N2 1.458(2) . ?
C5 C6 1.508(3) . ?
C5 N1 1.518(3) . ?
C6 C7 1.394(2) 6 ?
C6 C7 1.394(2) . ?
C7 C7 1.391(4) 2_556 ?
N1 C3 1.501(2) 6 ?
N2 C4 1.458(2) 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
F1 C8 C8 116.93(10) . 2 ?
F1 C8 C9 119.37(17) . . ?
C8 C8 C9 123.70(12) 2 . ?
C8 C9 C8 112.6(2) 6 . ?
C8 C9 C10 123.68(12) 6 . ?
C8 C9 C10 123.68(12) . . ?
C11 C10 C11 113.7(2) . 6 ?
C11 C10 C9 122.87(12) . . ?
C11 C10 C9 122.87(12) 6 . ?
N3 C11 C10 176.4(2) . . ?
N2 C1 C2 111.2(2) . . ?
N1 C2 C1 109.2(2) . . ?
N1 C3 C4 108.66(16) . . ?
N2 C4 C3 111.75(16) . . ?
C6 C5 N1 115.0(2) . . ?
C7 C6 C7 119.0(2) 6 . ?
C7 C6 C5 120.48(12) 6 . ?
C7 C6 C5 120.48(12) . . ?
C7 C7 C6 120.51(12) 2_556 . ?
C3 N1 C3 108.0(2) . 6 ?
C3 N1 C2 108.93(13) . . ?
C3 N1 C2 108.93(13) 6 . ?
C3 N1 C5 112.12(12) . . ?
C3 N1 C5 112.12(12) 6 . ?
C2 N1 C5 106.72(19) . . ?
C4 N2 C4 109.1(2) 6 . ?
C4 N2 C1 108.78(14) 6 . ?
C4 N2 C1 108.78(14) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 985166'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36.50 H22 F4 N8 O4.50'
_chemical_formula_weight         720.62

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0153(4)
_cell_length_b                   10.5291(7)
_cell_length_c                   11.0731(7)
_cell_angle_alpha                73.207(5)
_cell_angle_beta                 69.339(5)
_cell_angle_gamma                74.309(5)
_cell_volume                     822.17(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2529
_cell_measurement_theta_min      4.3657
_cell_measurement_theta_max      73.8917

_exptl_crystal_description       'Large Plate'
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.7687
_exptl_crystal_size_mid          0.2905
_exptl_crystal_size_min          0.1000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             369
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5420
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.37
_diffrn_reflns_theta_max         74.06
_reflns_number_total             3211
_reflns_number_gt                2749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0770P)²+0.3478P] 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         3211
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C13 C 0.9530(2) 0.93747(17) -0.07083(16) 0.0236(4) Uani 1 1 d . . .
C14 C 0.9691(2) 0.95021(17) 0.13116(16) 0.0235(4) Uani 1 1 d . . .
C15 C 0.9164(2) 0.88076(17) 0.06442(16) 0.0217(3) Uani 1 1 d . . .
C16 C 0.8290(2) 0.76442(17) 0.12961(16) 0.0235(4) Uani 1 1 d . . .
C17 C 0.7552(2) 0.72630(17) 0.26718(17) 0.0254(4) Uani 1 1 d . . .
C18 C 0.8011(2) 0.68272(17) 0.06085(16) 0.0231(3) Uani 1 1 d . . .
C20 C 1.0000 1.0000 0.5000 0.098(3) Uiso 0.50 2 d SP . .
N3 N 0.7729(2) 0.61020(15) 0.01221(15) 0.0285(3) Uani 1 1 d . . .
N4 N 0.6898(2) 0.68885(17) 0.37936(15) 0.0331(4) Uani 1 1 d . . .
O3 O 0.1645(16) 0.9493(12) -0.4707(12) 0.104(3) Uiso 0.25 1 d P . .
F1 F 0.90614(15) 0.88201(11) -0.14757(10) 0.0322(3) Uani 1 1 d . . .
F2 F 0.94333(15) 0.90473(11) 0.26279(10) 0.0320(3) Uani 1 1 d . . .
C1 C -0.0534(3) 0.6585(3) -0.4308(2) 0.0464(6) Uani 1 1 d . . .
H1 H -0.1574 0.6684 -0.4576 0.056 Uiso 1 1 calc R . .
C2 C 0.1131(3) 0.6715(3) -0.5243(2) 0.0477(6) Uani 1 1 d . . .
H2 H 0.1243 0.6910 -0.6159 0.057 Uiso 1 1 calc R . .
C3 C -0.0673(3) 0.6309(2) -0.29847(19) 0.0351(4) Uani 1 1 d . . .
H3 H -0.1813 0.6232 -0.2334 0.042 Uiso 1 1 calc R . .
C4 C 0.0845(2) 0.61469(18) -0.26169(17) 0.0258(4) Uani 1 1 d . . .
H4 H 0.0761 0.5945 -0.1706 0.031 Uiso 1 1 calc R . .
C5 C 0.2617(3) 0.6562(2) -0.48369(18) 0.0333(4) Uani 1 1 d . . .
H5 H 0.3761 0.6661 -0.5474 0.040 Uiso 1 1 calc R . .
C6 C 0.4121(2) 0.59884(17) -0.31104(17) 0.0238(4) Uani 1 1 d . . .
H6A H 0.5207 0.5917 -0.3889 0.029 Uiso 1 1 calc R . .
H6B H 0.4175 0.5105 -0.2478 0.029 Uiso 1 1 calc R . .
C7 C 0.4183(2) 0.70517(17) -0.24682(17) 0.0232(4) Uani 1 1 d . . .
C8 C 0.3827(2) 0.67808(17) -0.11026(17) 0.0234(4) Uani 1 1 d . . .
H8 H 0.3457 0.5963 -0.0562 0.028 Uiso 1 1 calc R . .
C9 C 0.4707(3) 0.82657(18) -0.32359(18) 0.0294(4) Uani 1 1 d . . .
H9 H 0.4940 0.8454 -0.4167 0.035 Uiso 1 1 calc R . .
C10 C 0.4890(3) 0.92015(19) -0.2650(2) 0.0332(4) Uani 1 1 d . . .
H10 H 0.5245 1.0027 -0.3183 0.040 Uiso 1 1 calc R . .
C11 C 0.4027(2) 0.77400(17) -0.05551(17) 0.0245(4) Uani 1 1 d . . .
C12 C 0.4561(2) 0.89403(18) -0.12958(19) 0.0296(4) Uani 1 1 d . . .
H12 H 0.4698 0.9570 -0.0889 0.036 Uiso 1 1 calc R . .
N1 N 0.24621(19) 0.62718(14) -0.35408(14) 0.0229(3) Uani 1 1 d . . .
N2 N 0.3670(2) 0.74381(16) 0.08919(16) 0.0287(3) Uani 1 1 d . . .
O1 O 0.31835(19) 0.63704(15) 0.15380(13) 0.0369(3) Uani 1 1 d . . .
O2 O 0.38799(19) 0.82693(15) 0.13827(14) 0.0377(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
C13 F1 1.3546(18) . ?
C13 C14 1.373(2) 2_775 ?
C13 C15 1.398(2) . ?
C14 F2 1.3544(19) . ?
C14 C13 1.373(2) 2_775 ?
C14 C15 1.399(2) . ?
C15 C16 1.452(2) . ?
C16 C17 1.404(2) . ?
C16 C18 1.404(2) . ?
C17 N4 1.159(2) . ?
C18 N3 1.158(2) . ?
C20 O3 1.396(12) 1_656 ?
C20 O3 1.396(12) 2_675 ?
O3 C20 1.396(12) 1_454 ?
C1 C3 1.379(3) . ?
C1 C2 1.383(3) . ?
C2 C5 1.371(3) . ?
C3 C4 1.369(3) . ?
C4 N1 1.350(2) . ?
C5 N1 1.345(2) . ?
C6 N1 1.495(2) . ?
C6 C7 1.509(2) . ?
C7 C8 1.393(2) . ?
C7 C9 1.394(3) . ?
C8 C11 1.387(2) . ?
C9 C10 1.388(3) . ?
C10 C12 1.384(3) . ?
C11 C12 1.378(3) . ?
C11 N2 1.477(2) . ?
N2 O1 1.226(2) . ?
N2 O2 1.228(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C13 C14 117.30(15) . 2_775 ?
F1 C13 C15 119.20(15) . . ?
C14 C13 C15 123.48(16) 2_775 . ?
F2 C14 C13 117.40(15) . 2_775 ?
F2 C14 C15 118.82(15) . . ?
C13 C14 C15 123.78(16) 2_775 . ?
C13 C15 C14 112.74(15) . . ?
C13 C15 C16 123.78(15) . . ?
C14 C15 C16 123.46(15) . . ?
C17 C16 C18 113.06(15) . . ?
C17 C16 C15 123.58(15) . . ?
C18 C16 C15 123.28(15) . . ?
N4 C17 C16 175.64(18) . . ?
N3 C18 C16 175.45(18) . . ?
O3 C20 O3 180.000(2) 1_656 2_675 ?
C3 C1 C2 119.51(18) . . ?
C5 C2 C1 119.36(18) . . ?
C4 C3 C1 119.42(18) . . ?
N1 C4 C3 120.38(16) . . ?
N1 C5 C2 120.34(17) . . ?
N1 C6 C7 113.64(13) . . ?
C8 C7 C9 119.73(16) . . ?
C8 C7 C6 119.57(15) . . ?
C9 C7 C6 120.57(15) . . ?
C11 C8 C7 118.05(16) . . ?
C10 C9 C7 120.50(17) . . ?
C12 C10 C9 120.45(17) . . ?
C12 C11 C8 123.20(16) . . ?
C12 C11 N2 119.04(15) . . ?
C8 C11 N2 117.75(15) . . ?
C11 C12 C10 118.06(16) . . ?
C5 N1 C4 120.97(15) . . ?
C5 N1 C6 119.73(14) . . ?
C4 N1 C6 119.16(14) . . ?
O1 N2 O2 123.54(16) . . ?
O1 N2 C11 118.25(14) . . ?
O2 N2 C11 118.21(16) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        74.06
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 985167'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H20 F4 N10 O8'
_chemical_formula_weight         796.62

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2034(5)
_cell_length_b                   10.8428(10)
_cell_length_c                   10.9912(10)
_cell_angle_alpha                95.047(7)
_cell_angle_beta                 109.560(7)
_cell_angle_gamma                108.643(7)
_cell_volume                     851.81(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2063
_cell_measurement_theta_min      4.3718
_cell_measurement_theta_max      73.8925

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.1645
_exptl_crystal_size_mid          0.0966
_exptl_crystal_size_min          0.0676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             406
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5597
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.37
_diffrn_reflns_theta_max         67.50
_reflns_number_total             3054
_reflns_number_gt                2393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0499P)²+0.1477P] 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         3054
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
F1 F 0.33019(17) 0.91778(11) 0.23411(10) 0.0394(3) Uani 1 1 d . . .
F2 F 0.70292(17) 0.87545(12) 0.65060(11) 0.0421(3) Uani 1 1 d . . .
O1 O 1.2984(2) 0.99523(15) 0.96101(15) 0.0455(4) Uani 1 1 d . . .
N5 N 1.0619(2) 0.70997(17) 0.40560(15) 0.0330(4) Uani 1 1 d . . .
O4 O 1.0021(2) 0.79119(16) 0.35626(14) 0.0442(4) Uani 1 1 d . . .
O3 O 1.0441(2) 0.60401(15) 0.34224(13) 0.0418(4) Uani 1 1 d . . .
N3 N 1.6067(2) 0.62658(14) 0.85578(14) 0.0244(3) Uani 1 1 d . . .
C5 C 0.6363(2) 0.69582(18) 0.43968(17) 0.0266(4) Uani 1 1 d . . .
N2 N 0.4063(2) 0.67770(17) 0.11976(16) 0.0356(4) Uani 1 1 d . . .
C3 C 0.5184(2) 0.88421(18) 0.43509(17) 0.0254(4) Uani 1 1 d . . .
C15 C 1.2385(2) 0.65344(18) 0.60691(18) 0.0267(4) Uani 1 1 d . . .
H15 H 1.2343 0.5779 0.5533 0.032 Uiso 1 1 calc R . .
C16 C 1.2468(3) 0.87271(18) 0.75882(19) 0.0289(4) Uani 1 1 d . . .
C2 C 0.4169(2) 0.95578(18) 0.36720(17) 0.0274(4) Uani 1 1 d . . .
C1 C 0.6007(3) 0.93546(19) 0.57140(18) 0.0275(4) Uani 1 1 d . . .
N4 N 1.2431(2) 0.98609(16) 0.84151(17) 0.0362(4) Uani 1 1 d . . .
C9 C 1.8712(3) 0.6385(2) 0.80935(19) 0.0334(4) Uani 1 1 d . . .
H9 H 1.9251 0.6242 0.7478 0.040 Uiso 1 1 calc R . .
C14 C 1.3296(2) 0.79045(18) 0.82105(18) 0.0274(4) Uani 1 1 d . . .
H14 H 1.3892 0.8095 0.9147 0.033 Uiso 1 1 calc R . .
C6 C 0.4623(3) 0.72185(19) 0.23217(19) 0.0289(4) Uani 1 1 d . . .
C17 C 1.1596(2) 0.74013(19) 0.55032(18) 0.0273(4) Uani 1 1 d . . .
C12 C 1.4005(2) 0.58169(18) 0.81056(18) 0.0268(4) Uani 1 1 d . . .
H12A H 1.3651 0.5694 0.8877 0.032 Uiso 1 1 calc R . .
H12B H 1.3426 0.4942 0.7477 0.032 Uiso 1 1 calc R . .
N1 N 0.7140(2) 0.62929(16) 0.48816(15) 0.0319(4) Uani 1 1 d . . .
C11 C 1.7135(3) 0.6821(2) 0.98409(18) 0.0329(4) Uani 1 1 d . . .
H11 H 1.6576 0.6980 1.0438 0.039 Uiso 1 1 calc R . .
C4 C 0.5359(2) 0.76803(18) 0.37030(17) 0.0267(4) Uani 1 1 d . . .
C10 C 1.6828(3) 0.60691(19) 0.76763(18) 0.0283(4) Uani 1 1 d . . .
H10 H 1.6055 0.5712 0.6766 0.034 Uiso 1 1 calc R . .
C13 C 1.3242(2) 0.67914(18) 0.74402(17) 0.0252(4) Uani 1 1 d . . .
C18 C 1.1608(2) 0.85112(19) 0.62322(19) 0.0290(4) Uani 1 1 d . . .
H18 H 1.1056 0.9093 0.5823 0.035 Uiso 1 1 calc R . .
O2 O 1.1820(3) 1.06323(16) 0.78489(17) 0.0552(5) Uani 1 1 d . . .
C7 C 1.9824(3) 0.6914(2) 0.9422(2) 0.0380(5) Uani 1 1 d . . .
H7 H 2.1127 0.7109 0.9730 0.046 Uiso 1 1 calc R . .
C8 C 1.9025(3) 0.7157(2) 1.0293(2) 0.0404(5) Uani 1 1 d . . .
H8 H 1.9780 0.7554 1.1200 0.048 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.351(2) . ?
F2 C1 1.358(2) . ?
O1 N4 1.221(2) . ?
N5 O4 1.222(2) . ?
N5 O3 1.229(2) . ?
N5 C17 1.472(2) . ?
N3 C11 1.343(2) . ?
N3 C10 1.352(2) . ?
N3 C12 1.488(2) . ?
C5 N1 1.160(2) . ?
C5 C4 1.403(3) . ?
N2 C6 1.158(2) . ?
C3 C1 1.395(3) . ?
C3 C2 1.397(3) . ?
C3 C4 1.463(2) . ?
C15 C17 1.383(3) . ?
C15 C13 1.391(3) . ?
C16 C18 1.379(3) . ?
C16 C14 1.382(3) . ?
C16 N4 1.478(2) . ?
C2 C1 1.379(3) 2_676 ?
C1 C2 1.379(3) 2_676 ?
N4 O2 1.220(2) . ?
C9 C10 1.370(3) . ?
C9 C7 1.385(3) . ?
C14 C13 1.391(3) . ?
C6 C4 1.407(3) . ?
C17 C18 1.381(3) . ?
C12 C13 1.515(2) . ?
C11 C8 1.369(3) . ?
C7 C8 1.379(3) . ?

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
O4 N5 O3 124.17(17) . . ?
O4 N5 C17 117.94(17) . . ?
O3 N5 C17 117.89(16) . . ?
C11 N3 C10 121.19(16) . . ?
C11 N3 C12 119.47(15) . . ?
C10 N3 C12 119.30(15) . . ?
N1 C5 C4 174.88(18) . . ?
C1 C3 C2 112.56(16) . . ?
C1 C3 C4 123.77(17) . . ?
C2 C3 C4 123.67(16) . . ?
C17 C15 C13 118.60(17) . . ?
C18 C16 C14 123.16(17) . . ?
C18 C16 N4 118.30(17) . . ?
C14 C16 N4 118.49(17) . . ?
F1 C2 C1 117.34(16) . 2_676 ?
F1 C2 C3 119.11(16) . . ?
C1 C2 C3 123.56(17) 2_676 . ?
F2 C1 C2 116.86(16) . 2_676 ?
F2 C1 C3 119.25(16) . . ?
C2 C1 C3 123.89(17) 2_676 . ?
O2 N4 O1 124.51(17) . . ?
O2 N4 C16 117.40(17) . . ?
O1 N4 C16 118.09(16) . . ?
C10 C9 C7 119.34(18) . . ?
C16 C14 C13 118.79(17) . . ?
N2 C6 C4 175.7(2) . . ?
C18 C17 C15 123.27(17) . . ?
C18 C17 N5 118.04(17) . . ?
C15 C17 N5 118.64(17) . . ?
N3 C12 C13 112.92(15) . . ?
N3 C11 C8 120.36(18) . . ?
C5 C4 C6 113.28(16) . . ?
C5 C4 C3 123.19(16) . . ?
C6 C4 C3 123.45(16) . . ?
N3 C10 C9 120.07(17) . . ?
C15 C13 C14 119.93(17) . . ?
C15 C13 C12 120.32(16) . . ?
C14 C13 C12 119.62(16) . . ?
C16 C18 C17 116.25(17) . . ?
C8 C7 C9 119.47(19) . . ?
C11 C8 C7 119.46(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 985168'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 F4 N6'
_chemical_formula_weight         538.50

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   18.3535(5)
_cell_length_b                   18.1472(5)
_cell_length_c                   7.4618(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.507(2)
_cell_angle_gamma                90.00
_cell_volume                     2435.31(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      3.4570
_cell_measurement_theta_max      76.6272

_exptl_crystal_description       'Triangular Plate'
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.7533
_exptl_crystal_size_mid          0.1865
_exptl_crystal_size_min          0.0822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.943

_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6007
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         67.47
_reflns_number_total             2189
_reflns_number_gt                1979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0520P)²+1.3120P] 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         2189
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C22 C 0.47325(7) 0.07127(7) 1.47025(17) 0.0244(3) Uani 1 1 d . . .
H22 H 0.4553 0.1191 1.4499 0.029 Uiso 1 1 calc R . .
F2 F 0.12335(4) 0.06851(4) 0.93523(12) 0.0327(2) Uani 1 1 d . . .
F1 F 0.00509(4) 0.14779(4) 0.95811(12) 0.0359(2) Uani 1 1 d . . .
C2 C 0.12329(7) -0.16028(8) 0.89972(18) 0.0300(3) Uani 1 1 d . . .
C6 C 0.20221(8) -0.06277(7) 1.03504(19) 0.0281(3) Uani 1 1 d . . .
C4 C 0.00177(7) 0.07395(7) 0.98464(17) 0.0251(3) Uani 1 1 d . . .
C3 C 0.06468(7) -0.04411(7) 0.98500(16) 0.0236(3) Uani 1 1 d . . .
N1 N 0.26260(7) -0.04276(7) 1.08835(19) 0.0392(3) Uani 1 1 d . . .
C1 C 0.12970(7) -0.08879(7) 0.97119(18) 0.0262(3) Uani 1 1 d . . .
C5 C 0.06309(7) 0.03265(7) 0.97068(17) 0.0243(3) Uani 1 1 d . . .
N2 N 0.12037(8) -0.21990(7) 0.84220(18) 0.0414(3) Uani 1 1 d . . .
N3 N 0.36777(6) -0.15661(6) 1.47815(14) 0.0232(2) Uani 1 1 d . . .
C7 C 0.30922(7) -0.12063(7) 1.52040(18) 0.0273(3) Uani 1 1 d . . .
H7 H 0.2931 -0.0767 1.4616 0.033 Uiso 1 1 calc R . .
C15 C 0.45584(7) -0.05939(7) 1.42533(17) 0.0229(3) Uani 1 1 d . . .
C16 C 0.42933(7) 0.01252(7) 1.39664(17) 0.0243(3) Uani 1 1 d . . .
H16 H 0.3820 0.0210 1.3278 0.029 Uiso 1 1 calc R . .
C8 C 0.27326(8) -0.14876(8) 1.6503(2) 0.0321(3) Uani 1 1 d . . .
H8 H 0.2331 -0.1238 1.6803 0.039 Uiso 1 1 calc R . .
C11 C 0.39171(8) -0.22084(8) 1.55880(18) 0.0298(3) Uani 1 1 d . . .
H11 H 0.4317 -0.2451 1.5260 0.036 Uiso 1 1 calc R . .
C9 C 0.29742(8) -0.21439(8) 1.73584(19) 0.0344(3) Uani 1 1 d . . .
H9 H 0.2736 -0.2340 1.8240 0.041 Uiso 1 1 calc R . .
C10 C 0.35732(9) -0.25078(8) 1.6895(2) 0.0352(3) Uani 1 1 d . . .
H10 H 0.3741 -0.2950 1.7460 0.042 Uiso 1 1 calc R . .
C14 C 0.40790(7) -0.12307(7) 1.34276(17) 0.0260(3) Uani 1 1 d . . .
H14A H 0.3720 -0.1059 1.2375 0.031 Uiso 1 1 calc R . .
H14B H 0.4388 -0.1602 1.3012 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C22 C16 1.3825(18) . ?
C22 C15 1.3939(19) 5_658 ?
F2 C5 1.3541(14) . ?
F1 C4 1.3577(15) . ?
C2 N2 1.1612(19) . ?
C2 C1 1.3987(19) . ?
C6 N1 1.1586(19) . ?
C6 C1 1.4029(19) . ?
C4 C5 1.3734(19) . ?
C4 C3 1.3937(18) 5_557 ?
C3 C4 1.3936(18) 5_557 ?
C3 C5 1.3969(19) . ?
C3 C1 1.4633(18) . ?
N3 C11 1.3448(17) . ?
N3 C7 1.3474(17) . ?
N3 C14 1.4934(16) . ?
C7 C8 1.375(2) . ?
C15 C22 1.3939(19) 5_658 ?
C15 C16 1.3942(18) . ?
C15 C14 1.5076(18) . ?
C8 C9 1.382(2) . ?
C11 C10 1.375(2) . ?
C9 C10 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C22 C15 120.54(12) . 5_658 ?
N2 C2 C1 177.83(15) . . ?
N1 C6 C1 178.60(15) . . ?
F1 C4 C5 117.79(11) . . ?
F1 C4 C3 118.26(12) . 5_557 ?
C5 C4 C3 123.87(12) . 5_557 ?
C4 C3 C5 113.22(12) 5_557 . ?
C4 C3 C1 123.27(12) 5_557 . ?
C5 C3 C1 123.51(11) . . ?
C2 C1 C6 116.34(12) . . ?
C2 C1 C3 122.21(12) . . ?
C6 C1 C3 121.42(12) . . ?
F2 C5 C4 117.79(12) . . ?
F2 C5 C3 119.25(12) . . ?
C4 C5 C3 122.91(12) . . ?
C11 N3 C7 121.33(11) . . ?
C11 N3 C14 119.66(11) . . ?
C7 N3 C14 118.99(11) . . ?
N3 C7 C8 120.16(13) . . ?
C22 C15 C16 119.27(12) 5_658 . ?
C22 C15 C14 120.90(12) 5_658 . ?
C16 C15 C14 119.83(12) . . ?
C22 C16 C15 120.19(12) . . ?
C7 C8 C9 119.37(13) . . ?
N3 C11 C10 120.31(13) . . ?
C8 C9 C10 119.57(13) . . ?
C11 C10 C9 119.26(13) . . ?
N3 C14 C15 111.24(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 985169'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_7F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 F4 N6'
_chemical_formula_weight         566.56

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   5.0039(3)
_cell_length_b                   15.2708(8)
_cell_length_c                   16.7605(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.417(6)
_cell_angle_gamma                90.00
_cell_volume                     1275.01(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.01(10)
_cell_measurement_reflns_used    2085
_cell_measurement_theta_min      3.9247
_cell_measurement_theta_max      77.2355

_exptl_crystal_description       Shard
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.4162
_exptl_crystal_size_mid          0.1219
_exptl_crystal_size_min          0.0167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_min  0.37812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3778
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         67.49
_reflns_number_total             3778
_reflns_number_gt                3524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1580P)²+2.6167P] 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         3778
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2812
_refine_ls_wR_factor_gt          0.2791
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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
C1 C 0.5150(8) 0.5883(2) 0.5003(2) 0.0280(8) Uani 1 1 d . . .
C2 C 0.6676(8) 0.5394(2) 0.4531(2) 0.0262(8) Uani 1 1 d . . .
C3 C 0.6628(8) 0.4474(2) 0.4493(2) 0.0258(8) Uani 1 1 d . . .
C4 C 0.8293(8) 0.3958(2) 0.3998(2) 0.0265(8) Uani 1 1 d . . .
C5 C 0.8790(8) 0.3057(3) 0.4131(2) 0.0306(9) Uani 1 1 d . . .
C6 C 0.9614(8) 0.4320(2) 0.3367(2) 0.0302(9) Uani 1 1 d . . .
C7 C 0.4287(10) 0.1330(3) 0.2887(3) 0.0387(10) Uani 1 1 d . . .
H7A H 0.3624 0.0829 0.2561 0.058 Uiso 1 1 calc R . .
H7B H 0.2796 0.1596 0.3140 0.058 Uiso 1 1 calc R . .
H7C H 0.5663 0.1132 0.3303 0.058 Uiso 1 1 calc R . .
C8 C 0.5478(8) 0.1996(3) 0.2363(2) 0.0289(9) Uani 1 1 d . . .
C9 C 0.4730(8) 0.2878(3) 0.2393(2) 0.0271(8) Uani 1 1 d . . .
H9 H 0.3463 0.3062 0.2746 0.033 Uiso 1 1 calc R . .
C10 C 0.7322(9) 0.1762(2) 0.1839(2) 0.0297(9) Uani 1 1 d . . .
H10 H 0.7864 0.1168 0.1806 0.036 Uiso 1 1 calc R . .
C11 C 0.8380(8) 0.2382(2) 0.1365(2) 0.0270(8) Uani 1 1 d . . .
H11 H 0.9655 0.2215 0.1008 0.032 Uiso 1 1 calc R . .
C12 C 0.5828(7) 0.3472(2) 0.1911(2) 0.0242(8) Uani 1 1 d . . .
H12 H 0.5319 0.4070 0.1934 0.029 Uiso 1 1 calc R . .
C13 C 0.8870(8) 0.3883(2) 0.0907(2) 0.0260(8) Uani 1 1 d . . .
H13A H 0.9946 0.3577 0.0526 0.031 Uiso 1 1 calc R . .
H13B H 1.0106 0.4253 0.1258 0.031 Uiso 1 1 calc R . .
C14 C 0.6832(7) 0.4459(2) 0.0444(2) 0.0219(7) Uani 1 1 d . . .
C15 C 0.7144(8) 0.5361(2) 0.0468(2) 0.0235(8) Uani 1 1 d . . .
H15 H 0.8616 0.5611 0.0789 0.028 Uiso 1 1 calc R . .
C16 C 0.4666(7) 0.4099(2) -0.0030(2) 0.0236(8) Uani 1 1 d . . .
H16 H 0.4434 0.3481 -0.0052 0.028 Uiso 1 1 calc R . .
N1 N 1.0701(8) 0.4568(2) 0.2826(2) 0.0363(8) Uani 1 1 d . . .
N2 N 0.9266(8) 0.2321(2) 0.4221(2) 0.0361(8) Uani 1 1 d . . .
N3 N 0.7623(6) 0.32241(18) 0.14041(17) 0.0219(7) Uani 1 1 d . . .
F1 F 0.8348(5) 0.58370(14) 0.40835(14) 0.0326(6) Uani 1 1 d . . .
F2 F 0.5485(5) 0.67613(13) 0.49834(13) 0.0318(6) 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
C1 F2 1.353(4) . ?
C1 C2 1.371(6) . ?
C1 C3 1.394(6) 3_666 ?
C2 F1 1.356(4) . ?
C2 C3 1.406(5) . ?
C3 C1 1.394(6) 3_666 ?
C3 C4 1.460(5) . ?
C4 C6 1.411(6) . ?
C4 C5 1.413(5) . ?
C5 N2 1.156(5) . ?
C6 N1 1.164(5) . ?
C7 C8 1.503(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.380(6) . ?
C8 C9 1.400(6) . ?
C9 C12 1.363(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9500 . ?
C11 N3 1.344(5) . ?
C11 H11 0.9500 . ?
C12 N3 1.348(5) . ?
C12 H12 0.9500 . ?
C13 N3 1.481(4) . ?
C13 C14 1.506(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.386(5) . ?
C14 C16 1.395(5) . ?
C15 C16 1.384(5) 3_665 ?
C15 H15 0.9500 . ?
C16 C15 1.384(5) 3_665 ?
C16 H16 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
F2 C1 C2 116.7(3) . . ?
F2 C1 C3 119.3(3) . 3_666 ?
C2 C1 C3 124.0(3) . 3_666 ?
F1 C2 C1 117.0(3) . . ?
F1 C2 C3 118.8(3) . . ?
C1 C2 C3 124.2(4) . . ?
C1 C3 C2 111.8(3) 3_666 . ?
C1 C3 C4 124.4(3) 3_666 . ?
C2 C3 C4 123.8(3) . . ?
C6 C4 C5 114.3(3) . . ?
C6 C4 C3 123.2(3) . . ?
C5 C4 C3 122.4(3) . . ?
N2 C5 C4 177.5(5) . . ?
N1 C6 C4 175.9(4) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C9 117.9(3) . . ?
C10 C8 C7 121.6(4) . . ?
C9 C8 C7 120.5(4) . . ?
C12 C9 C8 119.7(4) . . ?
C12 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C8 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
N3 C11 C10 120.4(3) . . ?
N3 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N3 C12 C9 121.1(3) . . ?
N3 C12 H12 119.5 . . ?
C9 C12 H12 119.5 . . ?
N3 C13 C14 112.7(3) . . ?
N3 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C16 119.2(3) . . ?
C15 C14 C13 119.8(3) . . ?
C16 C14 C13 121.0(3) . . ?
C16 C15 C14 120.7(3) 3_665 . ?
C16 C15 H15 119.7 3_665 . ?
C14 C15 H15 119.7 . . ?
C15 C16 C14 120.1(3) 3_665 . ?
C15 C16 H16 120.0 3_665 . ?
C14 C16 H16 120.0 . . ?
C11 N3 C12 120.4(3) . . ?
C11 N3 C13 119.1(3) . . ?
C12 N3 C13 120.4(3) . . ?

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
F2 C1 C2 F1 -0.8(5) . . . . ?
C3 C1 C2 F1 -178.8(3) 3_666 . . . ?
F2 C1 C2 C3 178.5(3) . . . . ?
C3 C1 C2 C3 0.4(7) 3_666 . . . ?
F1 C2 C3 C1 178.9(3) . . . 3_666 ?
C1 C2 C3 C1 -0.4(6) . . . 3_666 ?
F1 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C1 C3 C4 C6 165.5(4) 3_666 . . . ?
C2 C3 C4 C6 -16.1(6) . . . . ?
C1 C3 C4 C5 -16.8(6) 3_666 . . . ?
C2 C3 C4 C5 161.6(4) . . . . ?
C6 C4 C5 N2 8(10) . . . . ?
C3 C4 C5 N2 -170(10) . . . . ?
C5 C4 C6 N1 27(6) . . . . ?
C3 C4 C6 N1 -155(6) . . . . ?
C10 C8 C9 C12 -0.1(5) . . . . ?
C7 C8 C9 C12 -179.8(4) . . . . ?
C9 C8 C10 C11 0.1(6) . . . . ?
C7 C8 C10 C11 179.9(4) . . . . ?
C8 C10 C11 N3 -0.3(6) . . . . ?
C8 C9 C12 N3 0.2(5) . . . . ?
N3 C13 C14 C15 130.3(3) . . . . ?
N3 C13 C14 C16 -51.5(4) . . . . ?
C16 C14 C15 C16 0.1(6) . . . 3_665 ?
C13 C14 C15 C16 178.3(3) . . . 3_665 ?
C15 C14 C16 C15 -0.1(6) . . . 3_665 ?
C13 C14 C16 C15 -178.2(3) . . . 3_665 ?
C10 C11 N3 C12 0.4(5) . . . . ?
C10 C11 N3 C13 177.9(3) . . . . ?
C9 C12 N3 C11 -0.3(5) . . . . ?
C9 C12 N3 C13 -177.8(3) . . . . ?
C14 C13 N3 C11 130.8(3) . . . . ?
C14 C13 N3 C12 -51.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 985170'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_8F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H22 F4 N6'
_chemical_formula_weight         638.62

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4139(5)
_cell_length_b                   10.4083(11)
_cell_length_c                   13.9398(17)
_cell_angle_alpha                104.240(10)
_cell_angle_beta                 98.724(9)
_cell_angle_gamma                104.128(9)
_cell_volume                     719.36(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2151
_cell_measurement_theta_min      3.3532
_cell_measurement_theta_max      73.6088

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_size_max          0.2621
_exptl_crystal_size_mid          0.2049
_exptl_crystal_size_min          0.0198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4560
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         69.97
_reflns_number_total             2720
_reflns_number_gt                2359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0676P)²+0.0510P] 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         2720
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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
C19 C 0.1061(3) 1.13445(15) 0.50013(11) 0.0243(3) Uani 1 1 d . . .
H19 H 0.1786 1.2274 0.5003 0.029 Uiso 1 1 calc R . .
C18 C 0.0498(3) 0.89161(15) 0.43216(11) 0.0244(3) Uani 1 1 d . . .
H18 H 0.0823 0.8171 0.3860 0.029 Uiso 1 1 calc R . .
F2 F 0.35232(16) 0.59242(9) 0.34148(6) 0.0267(2) Uani 1 1 d . . .
F1 F 0.17369(15) 0.65917(8) 0.50544(6) 0.0258(2) Uani 1 1 d . . .
N2 N 0.8316(3) 0.20237(15) 0.26478(11) 0.0384(4) Uani 1 1 d . . .
N1 N 0.7808(3) 0.59147(14) 0.20824(10) 0.0313(3) Uani 1 1 d . . .
C6 C 0.7783(3) 0.30516(15) 0.29027(11) 0.0264(3) Uani 1 1 d . . .
C2 C 0.4308(3) 0.54434(14) 0.41910(10) 0.0211(3) Uani 1 1 d . . .
C3 C 0.5997(2) 0.46196(13) 0.40848(10) 0.0200(3) Uani 1 1 d . . .
C1 C 0.3382(2) 0.58008(13) 0.50557(10) 0.0207(3) Uani 1 1 d . . .
C5 C 0.7456(3) 0.51697(14) 0.25788(10) 0.0231(3) Uani 1 1 d . . .
C4 C 0.7049(3) 0.42691(14) 0.31819(11) 0.0222(3) Uani 1 1 d . . .
N3 N 0.2763(2) 0.95747(12) 0.26467(9) 0.0230(3) Uani 1 1 d . . .
C9 C 0.1599(3) 0.75838(14) 0.07843(11) 0.0251(3) Uani 1 1 d . . .
C15 C 0.0855(3) 0.95552(14) 0.19229(11) 0.0227(3) Uani 1 1 d . . .
H15 H -0.0074 1.0221 0.2054 0.027 Uiso 1 1 calc R . .
C17 C 0.1581(3) 1.02775(15) 0.43244(10) 0.0225(3) Uani 1 1 d . . .
C14 C 0.0182(3) 0.85694(14) 0.09660(11) 0.0231(3) Uani 1 1 d . . .
C16 C 0.3397(3) 1.06518(16) 0.36408(11) 0.0276(3) Uani 1 1 d . . .
H16A H 0.3288 1.1539 0.3524 0.033 Uiso 1 1 calc R . .
H16B H 0.5218 1.0791 0.3991 0.033 Uiso 1 1 calc R . .
C8 C 0.3587(3) 0.76401(16) 0.15851(12) 0.0285(3) Uani 1 1 d . . .
H8 H 0.4547 0.6984 0.1488 0.034 Uiso 1 1 calc R . .
C10 C 0.0930(3) 0.65933(16) -0.01889(13) 0.0334(4) Uani 1 1 d . . .
H10 H 0.1861 0.5930 -0.0332 0.040 Uiso 1 1 calc R . .
C12 C -0.2456(3) 0.75718(18) -0.07342(12) 0.0373(4) Uani 1 1 d . . .
H12 H -0.3832 0.7549 -0.1256 0.045 Uiso 1 1 calc R . .
C7 C 0.4146(3) 0.86263(16) 0.24970(12) 0.0277(3) Uani 1 1 d . . .
H7 H 0.5498 0.8659 0.3032 0.033 Uiso 1 1 calc R . .
C13 C -0.1851(3) 0.85545(17) 0.01928(12) 0.0307(3) Uani 1 1 d . . .
H13 H -0.2789 0.9218 0.0314 0.037 Uiso 1 1 calc R . .
C11 C -0.1049(3) 0.65967(18) -0.09169(12) 0.0389(4) Uani 1 1 d . . .
H11 H -0.1493 0.5925 -0.1564 0.047 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C19 C17 1.386(2) . ?
C19 C18 1.390(2) 2_576 ?
C18 C19 1.390(2) 2_576 ?
C18 C17 1.394(2) . ?
F2 C2 1.3537(16) . ?
F1 C1 1.3526(15) . ?
N2 C6 1.162(2) . ?
N1 C5 1.1611(19) . ?
C6 C4 1.4019(19) . ?
C2 C1 1.377(2) . ?
C2 C3 1.3978(18) . ?
C3 C1 1.396(2) 2_666 ?
C3 C4 1.4610(19) . ?
C1 C3 1.396(2) 2_666 ?
C5 C4 1.406(2) . ?
N3 C15 1.3225(19) . ?
N3 C7 1.3730(18) . ?
N3 C16 1.4828(18) . ?
C9 C8 1.407(2) . ?
C9 C10 1.419(2) . ?
C9 C14 1.4217(19) . ?
C15 C14 1.401(2) . ?
C17 C16 1.518(2) . ?
C14 C13 1.413(2) . ?
C8 C7 1.360(2) . ?
C10 C11 1.361(3) . ?
C12 C13 1.372(2) . ?
C12 C11 1.409(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 C19 C18 121.38(14) . 2_576 ?
C19 C18 C17 119.61(13) 2_576 . ?
N2 C6 C4 177.80(17) . . ?
F2 C2 C1 117.44(12) . . ?
F2 C2 C3 119.35(12) . . ?
C1 C2 C3 123.20(13) . . ?
C1 C3 C2 112.65(12) 2_666 . ?
C1 C3 C4 123.77(12) 2_666 . ?
C2 C3 C4 123.56(12) . . ?
F1 C1 C2 117.19(12) . . ?
F1 C1 C3 118.66(12) . 2_666 ?
C2 C1 C3 124.14(12) . 2_666 ?
N1 C5 C4 179.59(15) . . ?
C6 C4 C5 117.31(12) . . ?
C6 C4 C3 121.57(13) . . ?
C5 C4 C3 121.08(12) . . ?
C15 N3 C7 121.63(12) . . ?
C15 N3 C16 118.51(12) . . ?
C7 N3 C16 119.86(12) . . ?
C8 C9 C10 123.52(14) . . ?
C8 C9 C14 117.97(13) . . ?
C10 C9 C14 118.51(14) . . ?
N3 C15 C14 121.09(13) . . ?
C19 C17 C18 119.01(13) . . ?
C19 C17 C16 118.19(13) . . ?
C18 C17 C16 122.76(13) . . ?
C15 C14 C13 120.97(13) . . ?
C15 C14 C9 118.58(13) . . ?
C13 C14 C9 120.45(14) . . ?
N3 C16 C17 112.87(12) . . ?
C7 C8 C9 120.50(13) . . ?
C11 C10 C9 119.78(15) . . ?
C13 C12 C11 120.36(15) . . ?
C8 C7 N3 120.22(13) . . ?
C12 C13 C14 119.28(15) . . ?
C10 C11 C12 121.62(15) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        69.97
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 985171'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_9F4TCNQ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 F4 N6'
_chemical_formula_weight         564.54

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   6.5110(3)
_cell_length_b                   16.6335(6)
_cell_length_c                   11.4633(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.157(3)
_cell_angle_gamma                90.00
_cell_volume                     1238.22(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2551
_cell_measurement_theta_min      3.8604
_cell_measurement_theta_max      73.5774

_exptl_crystal_description       Plate
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.6705
_exptl_crystal_size_mid          0.2764
_exptl_crystal_size_min          0.0653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_min  0.76103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4660
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.69
_diffrn_reflns_theta_max         72.49
_reflns_number_total             2356
_reflns_number_gt                2075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0873P)²+0.2243P] 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         2356
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C14 C 0.1242(2) 0.78517(9) 0.11978(14) 0.0342(4) Uani 1 1 d . . .
H10A H 0.0087 0.7567 0.1514 0.051 Uiso 1 1 calc R . .
H10B H 0.2533 0.7686 0.1623 0.051 Uiso 1 1 calc R . .
H10C H 0.1292 0.7721 0.0367 0.051 Uiso 1 1 calc R . .
F1 F 0.17835(13) 0.14037(5) 0.44671(7) 0.0291(2) Uani 1 1 d . . .
F2 F 0.35676(13) 0.00698(5) 0.39456(8) 0.0297(2) Uani 1 1 d . . .
C1 C -0.3760(2) 0.15350(8) 0.62342(12) 0.0267(3) Uani 1 1 d . . .
N2 N -0.5174(2) 0.16016(8) 0.67799(12) 0.0321(3) Uani 1 1 d . . .
C5 C 0.0846(2) 0.07154(8) 0.47544(12) 0.0242(3) Uani 1 1 d . . .
C6 C 0.1789(2) 0.00077(8) 0.44767(12) 0.0250(3) Uani 1 1 d . . .
C2 C -0.1333(2) 0.22699(9) 0.52529(13) 0.0286(3) Uani 1 1 d . . .
N1 N -0.0921(2) 0.29239(8) 0.50094(13) 0.0401(4) Uani 1 1 d . . .
C4 C -0.1003(2) 0.07546(8) 0.52939(12) 0.0240(3) Uani 1 1 d . . .
C3 C -0.2000(2) 0.15055(8) 0.55887(12) 0.0259(3) Uani 1 1 d . . .
N3 N 0.09622(18) 0.87269(7) 0.13325(10) 0.0271(3) Uani 1 1 d . . .
C11 C 0.0543(2) 1.03766(9) 0.15436(11) 0.0250(3) Uani 1 1 d . . .
C16 C -0.0980(2) 0.98410(9) 0.19228(12) 0.0240(3) Uani 1 1 d . . .
C13 C 0.2469(2) 0.92270(9) 0.09617(13) 0.0288(3) Uani 1 1 d . . .
H13 H 0.3643 0.9005 0.0635 0.035 Uiso 1 1 calc R . .
C15 C -0.0688(2) 0.90133(9) 0.17967(12) 0.0260(3) Uani 1 1 d . . .
H15 H -0.1693 0.8651 0.2049 0.031 Uiso 1 1 calc R . .
C7 C -0.2760(2) 1.01441(9) 0.24069(12) 0.0274(3) Uani 1 1 d . . .
H7 H -0.3768 0.9786 0.2667 0.033 Uiso 1 1 calc R . .
C9 C -0.1508(2) 1.14903(9) 0.21231(13) 0.0317(3) Uani 1 1 d . . .
H9 H -0.1708 1.2054 0.2191 0.038 Uiso 1 1 calc R . .
C12 C 0.2281(2) 1.00347(9) 0.10614(12) 0.0279(3) Uani 1 1 d . . .
H12 H 0.3329 1.0375 0.0805 0.033 Uiso 1 1 calc R . .
C8 C -0.3019(2) 1.09560(9) 0.24971(13) 0.0309(3) Uani 1 1 d . . .
H8 H -0.4220 1.1163 0.2813 0.037 Uiso 1 1 calc R . .
C10 C 0.0235(2) 1.12085(9) 0.16660(13) 0.0298(3) Uani 1 1 d . . .
H10 H 0.1242 1.1576 0.1430 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C14 N3 1.4766(18) . ?
F1 C5 1.3496(16) . ?
F2 C6 1.3505(16) . ?
C1 N2 1.155(2) . ?
C1 C3 1.409(2) . ?
C5 C6 1.3756(19) . ?
C5 C4 1.394(2) . ?
C6 C4 1.3995(19) 3_556 ?
C2 N1 1.159(2) . ?
C2 C3 1.4063(19) . ?
C4 C6 1.3995(19) 3_556 ?
C4 C3 1.4583(19) . ?
N3 C15 1.3219(19) . ?
N3 C13 1.3766(19) . ?
C11 C10 1.407(2) . ?
C11 C12 1.415(2) . ?
C11 C16 1.4238(19) . ?
C16 C15 1.399(2) . ?
C16 C7 1.414(2) . ?
C13 C12 1.355(2) . ?
C7 C8 1.366(2) . ?
C9 C10 1.367(2) . ?
C9 C8 1.415(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C3 176.28(15) . . ?
F1 C5 C6 116.87(13) . . ?
F1 C5 C4 119.27(12) . . ?
C6 C5 C4 123.86(13) . . ?
F2 C6 C5 116.79(12) . . ?
F2 C6 C4 119.41(12) . 3_556 ?
C5 C6 C4 123.80(14) . 3_556 ?
N1 C2 C3 174.69(15) . . ?
C5 C4 C6 112.34(12) . 3_556 ?
C5 C4 C3 123.76(12) . . ?
C6 C4 C3 123.89(14) 3_556 . ?
C2 C3 C1 113.02(12) . . ?
C2 C3 C4 124.03(13) . . ?
C1 C3 C4 122.94(13) . . ?
C15 N3 C13 121.64(13) . . ?
C15 N3 C14 120.50(12) . . ?
C13 N3 C14 117.87(12) . . ?
C10 C11 C12 123.94(13) . . ?
C10 C11 C16 118.53(13) . . ?
C12 C11 C16 117.53(13) . . ?
C15 C16 C7 120.85(13) . . ?
C15 C16 C11 118.79(13) . . ?
C7 C16 C11 120.36(14) . . ?
C12 C13 N3 120.19(14) . . ?
N3 C15 C16 121.12(13) . . ?
C8 C7 C16 119.42(14) . . ?
C10 C9 C8 121.03(14) . . ?
C13 C12 C11 120.74(13) . . ?
C7 C8 C9 120.39(14) . . ?
C9 C10 C11 120.25(13) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        72.49
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 985172'
