# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# 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_2

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H F9 N2'
_chemical_formula_sum            'C9 H F9 N2'
_chemical_formula_weight         308.12
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_Int_Tables_number      145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   12.4390(7)
_cell_length_b                   12.4390(7)
_cell_length_c                   5.5990(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     750.26(17)
_cell_formula_units_Z            3
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6729
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      36.97
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_number            7456
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             912
_reflns_number_gt                900
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0732P)²+2.6562P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         912
_refine_ls_number_parameters     124
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.097

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.4338(6) 1.0576(6) 0.1064(12) 0.0203(14) Uani 1 1 d . . .
C3A C 0.3310(6) 1.0268(6) 0.2645(12) 0.0191(13) Uani 1 1 d . . .
C4 C 0.2111(7) 0.9269(7) 0.2972(13) 0.0225(14) Uani 1 1 d . . .
C5 C 0.1404(7) 0.9300(7) 0.4834(14) 0.0249(14) Uani 1 1 d . . .
C6 C 0.1882(7) 1.0346(7) 0.6375(13) 0.0249(15) Uani 1 1 d . . .
C7 C 0.3040(7) 1.1347(7) 0.6052(13) 0.0231(15) Uani 1 1 d . . .
C7A C 0.3741(7) 1.1303(7) 0.4151(13) 0.0235(15) Uani 1 1 d . . .
C8 C 0.4477(7) 0.9800(7) -0.0795(13) 0.0258(15) Uani 1 1 d . . .
C9 C 0.4818(7) 0.8861(7) 0.0219(14) 0.0289(16) Uani 1 1 d . . .
N1 N 0.4920(5) 1.2130(5) 0.3440(12) 0.0239(13) Uani 1 1 d D . .
H1 H 0.547(6) 1.287(3) 0.380(16) 0.029 Uiso 1 1 d D . .
N2 N 0.5276(5) 1.1691(6) 0.1576(10) 0.023 Uani 1 1 d . . .
F4 F 0.1627(4) 0.8266(4) 0.1551(8) 0.03 Uani 1 1 d . . .
F5 F 0.0274(4) 0.8361(4) 0.5257(9) 0.033 Uani 1 1 d . . .
F6 F 0.1162(4) 1.0301(5) 0.8173(8) 0.035 Uani 1 1 d . . .
F7 F 0.3502(4) 1.2309(4) 0.7566(8) 0.034 Uani 1 1 d . . .
F8 F 0.3419(4) 0.9145(4) -0.2037(8) 0.031 Uani 1 1 d . . .
F9 F 0.5382(4) 1.0530(5) -0.2339(9) 0.036 Uani 1 1 d . . .
F10 F 0.3974(5) 0.8130(5) 0.1789(9) 0.043 Uani 1 1 d . . .
F11 F 0.4852(5) 0.8153(5) -0.1508(10) 0.045 Uani 1 1 d . . .
F12 F 0.5910(5) 0.9445(6) 0.1267(10) 0.047 Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 N2 1.322(9) . ?
C3 C3A 1.441(9) . ?
C3 C8 1.487(10) . ?
C3A C4 1.396(10) . ?
C3A C7A 1.402(10) . ?
C4 F4 1.342(8) . ?
C4 C5 1.377(11) . ?
C5 F5 1.325(9) . ?
C5 C6 1.421(11) . ?
C6 F6 1.330(9) . ?
C6 C7 1.365(11) . ?
C7 F7 1.340(9) . ?
C7 C7A 1.394(10) . ?
C7A N1 1.363(9) . ?
C8 F8 1.344(9) . ?
C8 F9 1.348(9) . ?
C8 C9 1.537(10) . ?
C9 F12 1.315(10) . ?
C9 F10 1.322(9) . ?
C9 F11 1.323(10) . ?
N1 N2 1.351(9) . ?
N1 H1 0.848(11) . ?

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 C3 C3A 110.2(6) . . ?
N2 C3 C8 120.3(6) . . ?
C3A C3 C8 129.3(6) . . ?
C4 C3A C7A 119.2(6) . . ?
C4 C3A C3 136.7(6) . . ?
C7A C3A C3 104.1(6) . . ?
F4 C4 C5 118.6(6) . . ?
F4 C4 C3A 122.2(6) . . ?
C5 C4 C3A 119.1(6) . . ?
F5 C5 C4 121.4(7) . . ?
F5 C5 C6 118.2(6) . . ?
C4 C5 C6 120.3(7) . . ?
F6 C6 C7 121.4(7) . . ?
F6 C6 C5 117.2(7) . . ?
C7 C6 C5 121.5(6) . . ?
F7 C7 C6 121.1(6) . . ?
F7 C7 C7A 121.4(7) . . ?
C6 C7 C7A 117.5(6) . . ?
N1 C7A C7 130.7(7) . . ?
N1 C7A C3A 106.9(6) . . ?
C7 C7A C3A 122.3(6) . . ?
F8 C8 F9 108.1(6) . . ?
F8 C8 C3 111.0(6) . . ?
F9 C8 C3 109.9(6) . . ?
F8 C8 C9 106.8(6) . . ?
F9 C8 C9 107.1(6) . . ?
C3 C8 C9 113.6(6) . . ?
F12 C9 F10 109.2(7) . . ?
F12 C9 F11 109.1(7) . . ?
F10 C9 F11 107.9(6) . . ?
F12 C9 C8 110.3(6) . . ?
F10 C9 C8 110.0(6) . . ?
F11 C9 C8 110.4(6) . . ?
N2 N1 C7A 111.5(6) . . ?
N2 N1 H1 112(6) . . ?
C7A N1 H1 137(6) . . ?
C3 N2 N1 107.2(6) . . ?
_database_code_depnum_ccdc_archive 'CCDC 982666'
#######################################################################
#
#                 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_3

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H F11 N2'
_chemical_formula_sum            'C10 H F11 N2'
_chemical_formula_weight         358.13
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.1335(3)
_cell_length_b                   9.1624(5)
_cell_length_c                   24.8250(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1167.65(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      32.36
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_number            26389
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         33.04
_diffrn_reflns_theta_full        33.04
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_reflns_number_total             2432
_reflns_number_gt                2121
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0553P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.1879(3) 0.61736(19) 0.09062(6) 0.0190(3) Uani 1 1 d . . .
C3A C 0.0397(3) 0.48733(18) 0.09405(6) 0.0178(3) Uani 1 1 d . . .
C4 C 0.0207(4) 0.36625(19) 0.12846(6) 0.0226(3) Uani 1 1 d . . .
C5 C -0.1633(4) 0.2626(2) 0.11816(7) 0.0273(4) Uani 1 1 d . . .
C6 C -0.3345(4) 0.2755(2) 0.07424(8) 0.0271(4) Uani 1 1 d . . .
C7 C -0.3189(4) 0.3912(2) 0.03969(7) 0.0240(3) Uani 1 1 d . . .
C7A C -0.1282(3) 0.49606(19) 0.04940(6) 0.0193(3) Uani 1 1 d . . .
C8 C 0.3791(4) 0.6804(2) 0.12956(6) 0.0211(3) Uani 1 1 d . . .
C9 C 0.2408(4) 0.7638(2) 0.17568(7) 0.0224(3) Uani 1 1 d . . .
C10 C 0.4131(4) 0.8200(2) 0.22198(7) 0.0287(4) Uani 1 1 d . . .
N1 N -0.0701(3) 0.62094(17) 0.02298(6) 0.0225(3) Uani 1 1 d . . .
H1 H -0.153(5) 0.660(3) -0.0025(9) 0.027 Uiso 1 1 d . . .
N2 N 0.1194(3) 0.69622(17) 0.04806(5) 0.0217(3) Uani 1 1 d . . .
F4 F 0.1801(3) 0.35088(14) 0.17024(5) 0.0340(3) Uani 1 1 d . . .
F5 F -0.1865(3) 0.14584(13) 0.14966(6) 0.0432(4) Uani 1 1 d . . .
F6 F -0.5129(3) 0.17152(15) 0.06662(6) 0.0431(4) Uani 1 1 d . . .
F7 F -0.4821(3) 0.40479(15) -0.00199(5) 0.0359(3) Uani 1 1 d . . .
F8 F 0.5410(2) 0.77454(14) 0.10416(4) 0.0329(3) Uani 1 1 d . . .
F9 F 0.5261(2) 0.57401(13) 0.15185(4) 0.0285(2) Uani 1 1 d . . .
F10 F 0.1192(3) 0.87931(16) 0.15384(6) 0.0414(3) Uani 1 1 d . . .
F11 F 0.0633(2) 0.67451(15) 0.19719(5) 0.0342(3) Uani 1 1 d . . .
F12 F 0.2675(3) 0.89501(17) 0.25614(5) 0.0457(4) Uani 1 1 d . . .
F13 F 0.5998(3) 0.90559(16) 0.20384(6) 0.0441(4) Uani 1 1 d . . .
F14 F 0.5208(4) 0.71035(16) 0.24818(5) 0.0443(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 N2 1.327(2) . ?
C3 C3A 1.416(2) . ?
C3 C8 1.494(2) . ?
C3A C4 1.404(2) . ?
C3A C7A 1.406(2) . ?
C4 F4 1.329(2) . ?
C4 C5 1.364(3) . ?
C5 F5 1.330(2) . ?
C5 C6 1.406(3) . ?
C6 F6 1.335(2) . ?
C6 C7 1.365(3) . ?
C7 F7 1.337(2) . ?
C7 C7A 1.393(2) . ?
C7A N1 1.352(2) . ?
C8 F9 1.351(2) . ?
C8 F8 1.354(2) . ?
C8 C9 1.549(2) . ?
C9 F11 1.336(2) . ?
C9 F10 1.343(2) . ?
C9 C10 1.539(3) . ?
C10 F13 1.318(2) . ?
C10 F14 1.318(3) . ?
C10 F12 1.323(2) . ?
N1 N2 1.345(2) . ?
N1 H1 0.84(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 C3 C3A 111.31(15) . . ?
N2 C3 C8 118.59(15) . . ?
C3A C3 C8 129.76(14) . . ?
C4 C3A C7A 118.82(16) . . ?
C4 C3A C3 137.63(16) . . ?
C7A C3A C3 103.54(14) . . ?
F4 C4 C5 119.95(15) . . ?
F4 C4 C3A 121.07(17) . . ?
C5 C4 C3A 118.98(16) . . ?
F5 C5 C4 120.79(18) . . ?
F5 C5 C6 117.90(18) . . ?
C4 C5 C6 121.31(16) . . ?
F6 C6 C7 120.33(18) . . ?
F6 C6 C5 118.59(17) . . ?
C7 C6 C5 121.08(17) . . ?
F7 C7 C6 121.46(18) . . ?
F7 C7 C7A 120.65(16) . . ?
C6 C7 C7A 117.89(16) . . ?
N1 C7A C7 130.91(16) . . ?
N1 C7A C3A 107.18(15) . . ?
C7 C7A C3A 121.86(15) . . ?
F9 C8 F8 107.89(15) . . ?
F9 C8 C3 110.66(14) . . ?
F8 C8 C3 110.40(13) . . ?
F9 C8 C9 108.01(13) . . ?
F8 C8 C9 108.15(15) . . ?
C3 C8 C9 111.61(15) . . ?
F11 C9 F10 109.09(17) . . ?
F11 C9 C10 107.34(14) . . ?
F10 C9 C10 107.77(15) . . ?
F11 C9 C8 107.81(15) . . ?
F10 C9 C8 107.66(14) . . ?
C10 C9 C8 117.00(16) . . ?
F13 C10 F14 108.5(2) . . ?
F13 C10 F12 108.69(17) . . ?
F14 C10 F12 108.46(17) . . ?
F13 C10 C9 111.22(15) . . ?
F14 C10 C9 110.78(16) . . ?
F12 C10 C9 109.15(18) . . ?
N2 N1 C7A 111.64(14) . . ?
N2 N1 H1 119.5(17) . . ?
C7A N1 H1 127.9(18) . . ?
C3 N2 N1 106.31(14) . . ?
_database_code_depnum_ccdc_archive 'CCDC 982667'
#######################################################################
#
#                 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_4

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H1 F13 N2'
_chemical_formula_sum            'C11 H1 F13 N2'
_chemical_formula_weight         408.13
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.3577(5)
_cell_length_b                   5.1436(2)
_cell_length_c                   27.2757(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.507(5)
_cell_angle_gamma                90
_cell_volume                     1294.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5655
_cell_measurement_theta_min      2.8697
_cell_measurement_theta_max      31.3748
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.094
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.8806
_exptl_absorpt_correction_T_max  0.9981

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 8.2632
_diffrn_orient_matrix_ub_11      -0.0123868
_diffrn_orient_matrix_ub_12      0.0394788
_diffrn_orient_matrix_ub_13      -0.0252707
_diffrn_orient_matrix_ub_21      -0.0012827
_diffrn_orient_matrix_ub_22      0.1318463
_diffrn_orient_matrix_ub_23      0.0075195
_diffrn_orient_matrix_ub_31      0.0758376
_diffrn_orient_matrix_ub_32      0.0087219
_diffrn_orient_matrix_ub_33      0.0004318
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_number            8638
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2457
_reflns_number_gt                2018
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0619P)²+0.8428P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.0821(2) 0.2947(4) 0.16790(7) 0.0216(4) Uani 1 1 d . . .
C3A C -0.0501(2) 0.4334(4) 0.16448(7) 0.0205(4) Uani 1 1 d . . .
C4 C -0.1849(2) 0.4407(4) 0.13345(8) 0.0266(5) Uani 1 1 d . . .
C5 C -0.2843(2) 0.6183(5) 0.14252(8) 0.0328(5) Uani 1 1 d . . .
C6 C -0.2550(2) 0.7929(5) 0.18211(9) 0.0333(5) Uani 1 1 d . . .
C7 C -0.1262(2) 0.7886(4) 0.21338(8) 0.0284(5) Uani 1 1 d . . .
C7A C -0.0246(2) 0.6056(4) 0.20464(7) 0.0223(4) Uani 1 1 d . . .
C8 C 0.1303(2) 0.1064(4) 0.13252(7) 0.0242(4) Uani 1 1 d . . .
C9 C 0.1846(2) 0.2474(4) 0.08917(7) 0.0221(4) Uani 1 1 d . . .
C10 C 0.2473(2) 0.0787(4) 0.05129(8) 0.0259(5) Uani 1 1 d . . .
C11 C 0.2856(2) 0.2231(4) 0.00615(8) 0.0331(5) Uani 1 1 d . . .
N1 N 0.11133(19) 0.5590(3) 0.22899(6) 0.0257(4) Uani 1 1 d D . .
H1 H 0.159(2) 0.657(4) 0.2534(7) 0.031 Uiso 1 1 d D . .
N2 N 0.17669(18) 0.3731(3) 0.20639(6) 0.0250(4) Uani 1 1 d . . .
F4 F -0.21672(14) 0.2761(3) 0.09580(5) 0.0390(4) Uani 1 1 d . . .
F5 F -0.41410(14) 0.6286(3) 0.11393(6) 0.0544(5) Uani 1 1 d . . .
F6 F -0.35696(16) 0.9645(3) 0.18874(6) 0.0517(4) Uani 1 1 d . . .
F7 F -0.09652(16) 0.9559(3) 0.25133(5) 0.0427(4) Uani 1 1 d . . .
F8 F 0.02159(15) -0.0531(2) 0.11343(5) 0.0359(3) Uani 1 1 d . . .
F9 F 0.23922(16) -0.0420(3) 0.15623(5) 0.0407(4) Uani 1 1 d . . .
F10 F 0.07222(14) 0.3821(2) 0.06483(5) 0.0330(3) Uani 1 1 d . . .
F11 F 0.28675(14) 0.4159(3) 0.10897(5) 0.0381(3) Uani 1 1 d . . .
F12 F 0.36664(18) -0.0366(4) 0.07408(6) 0.0583(5) Uani 1 1 d . . .
F13 F 0.15091(18) -0.1040(3) 0.03393(6) 0.0510(4) Uani 1 1 d . . .
F14 F 0.3733(2) 0.4150(4) 0.01938(7) 0.0760(7) Uani 1 1 d . . .
F15 F 0.16848(19) 0.3150(4) -0.02157(6) 0.0711(6) Uani 1 1 d . . .
F16 F 0.34715(18) 0.0640(3) -0.02139(5) 0.0501(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 N2 1.319(3) . ?
C3 C3A 1.418(3) . ?
C3 C8 1.489(3) . ?
C3A C7A 1.398(3) . ?
C3A C4 1.399(3) . ?
C4 F4 1.326(2) . ?
C4 C5 1.355(3) . ?
C5 F5 1.332(3) . ?
C5 C6 1.396(3) . ?
C6 F6 1.334(3) . ?
C6 C7 1.357(3) . ?
C7 F7 1.339(2) . ?
C7 C7A 1.386(3) . ?
C7A N1 1.355(3) . ?
C8 F8 1.343(2) . ?
C8 F9 1.350(2) . ?
C8 C9 1.543(3) . ?
C9 F11 1.337(2) . ?
C9 F10 1.340(2) . ?
C9 C10 1.538(3) . ?
C10 F12 1.325(2) . ?
C10 F13 1.334(3) . ?
C10 C11 1.530(3) . ?
C11 F14 1.296(3) . ?
C11 F16 1.307(3) . ?
C11 F15 1.313(3) . ?
N1 N2 1.339(2) . ?
N1 H1 0.891(10) . ?

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 C3 C3A 111.21(17) . . ?
N2 C3 C8 118.65(17) . . ?
C3A C3 C8 129.73(17) . . ?
C7A C3A C4 118.49(19) . . ?
C7A C3A C3 103.49(16) . . ?
C4 C3A C3 138.01(19) . . ?
F4 C4 C5 119.91(19) . . ?
F4 C4 C3A 121.06(19) . . ?
C5 C4 C3A 119.0(2) . . ?
F5 C5 C4 120.5(2) . . ?
F5 C5 C6 118.1(2) . . ?
C4 C5 C6 121.4(2) . . ?
F6 C6 C7 120.5(2) . . ?
F6 C6 C5 118.5(2) . . ?
C7 C6 C5 121.1(2) . . ?
F7 C7 C6 121.6(2) . . ?
F7 C7 C7A 120.57(19) . . ?
C6 C7 C7A 117.8(2) . . ?
N1 C7A C7 130.59(19) . . ?
N1 C7A C3A 107.26(17) . . ?
C7 C7A C3A 122.12(19) . . ?
F8 C8 F9 107.71(16) . . ?
F8 C8 C3 110.96(17) . . ?
F9 C8 C3 110.05(16) . . ?
F8 C8 C9 108.31(16) . . ?
F9 C8 C9 108.35(16) . . ?
C3 C8 C9 111.35(16) . . ?
F11 C9 F10 108.37(16) . . ?
F11 C9 C10 108.07(16) . . ?
F10 C9 C10 108.31(16) . . ?
F11 C9 C8 107.43(16) . . ?
F10 C9 C8 106.98(15) . . ?
C10 C9 C8 117.40(17) . . ?
F12 C10 F13 108.61(18) . . ?
F12 C10 C11 107.66(18) . . ?
F13 C10 C11 106.91(17) . . ?
F12 C10 C9 108.83(17) . . ?
F13 C10 C9 108.97(17) . . ?
C11 C10 C9 115.66(18) . . ?
F14 C11 F16 108.58(19) . . ?
F14 C11 F15 108.4(2) . . ?
F16 C11 F15 107.4(2) . . ?
F14 C11 C10 111.55(19) . . ?
F16 C11 C10 110.02(19) . . ?
F15 C11 C10 110.71(18) . . ?
N2 N1 C7A 111.33(16) . . ?
N2 N1 H1 122.7(16) . . ?
C7A N1 H1 125.1(16) . . ?
C3 N2 N1 106.69(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.891(10) 2.064(13) 2.915(2) 159(2) 2
_database_code_depnum_ccdc_archive 'CCDC 982668'
#######################################################################
#
#                 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_5

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H F17 N2'
_chemical_formula_sum            'C13 H F17 N2 '
_chemical_formula_weight         508.16
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   14.1749(9)
_cell_length_b                   6.3085(5)
_cell_length_c                   18.2579(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.598(8)
_cell_angle_gamma                90
_cell_volume                     1609.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3505
_cell_measurement_theta_min      3.3727
_cell_measurement_theta_max      29.1224
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  0.915

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 16.1978
_diffrn_orient_matrix_ub_11      -0.0255596
_diffrn_orient_matrix_ub_12      0.0692317
_diffrn_orient_matrix_ub_13      -0.0267968
_diffrn_orient_matrix_ub_21      0.001324
_diffrn_orient_matrix_ub_22      0.0800217
_diffrn_orient_matrix_ub_23      0.0275154
_diffrn_orient_matrix_ub_31      0.0438102
_diffrn_orient_matrix_ub_32      0.0379743
_diffrn_orient_matrix_ub_33      -0.008852
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_number            13951
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3287
_reflns_number_gt                1638
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0796P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3287
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.8661(2) 1.3045(5) 0.38356(18) 0.0301(8) Uani 1 1 d . . .
C3A C 0.9090(2) 1.1155(5) 0.36256(18) 0.0297(8) Uani 1 1 d . . .
C4 C 0.8859(2) 0.9486(6) 0.31206(18) 0.0334(8) Uani 1 1 d . . .
C5 C 0.9501(2) 0.7888(6) 0.3104(2) 0.0414(9) Uani 1 1 d . . .
C6 C 1.0388(2) 0.7899(6) 0.3575(2) 0.0383(9) Uani 1 1 d . . .
C7 C 1.0639(2) 0.9468(6) 0.40647(19) 0.0345(8) Uani 1 1 d . . .
C7A C 0.99921(19) 1.1121(5) 0.40877(18) 0.0290(8) Uani 1 1 d . . .
C8 C 0.7678(2) 1.3915(6) 0.3553(2) 0.0360(9) Uani 1 1 d . . .
C9 C 0.6893(2) 1.2799(5) 0.39052(19) 0.0312(8) Uani 1 1 d . . .
C10 C 0.5841(2) 1.3410(6) 0.3583(2) 0.0357(8) Uani 1 1 d . . .
C11 C 0.5071(2) 1.2323(6) 0.3959(2) 0.0366(9) Uani 1 1 d . . .
C12 C 0.4035(2) 1.3010(7) 0.3685(2) 0.0474(10) Uani 1 1 d . . .
C13 C 0.3261(2) 1.1885(7) 0.4026(2) 0.0502(11) Uani 1 1 d . . .
N1 N 1.00390(19) 1.2871(5) 0.45183(18) 0.0354(7) Uani 1 1 d . . .
N2 N 0.92263(17) 1.4050(4) 0.43702(16) 0.0355(7) Uani 1 1 d . . .
F4 F 0.80201(12) 0.9437(3) 0.26671(11) 0.0487(6) Uani 1 1 d . . .
F5 F 0.92940(15) 0.6277(4) 0.26245(12) 0.0596(7) Uani 1 1 d . . .
F6 F 1.09739(14) 0.6230(3) 0.35360(13) 0.0604(6) Uani 1 1 d . . .
F7 F 1.14733(12) 0.9459(3) 0.45450(11) 0.0480(6) Uani 1 1 d . . .
F8 F 0.76529(13) 1.5991(3) 0.37120(14) 0.0586(7) Uani 1 1 d . . .
F9 F 0.74811(12) 1.3698(4) 0.28121(11) 0.0529(6) Uani 1 1 d . . .
F10 F 0.70606(12) 1.3251(4) 0.46320(11) 0.0497(6) Uani 1 1 d . . .
F11 F 0.69881(12) 1.0705(3) 0.38283(12) 0.0472(6) Uani 1 1 d . . .
F12 F 0.57516(14) 1.5493(4) 0.36421(16) 0.0724(8) Uani 1 1 d . . .
F13 F 0.56764(13) 1.2893(5) 0.28668(12) 0.0775(9) Uani 1 1 d . . .
F14 F 0.52679(14) 1.2593(5) 0.46815(13) 0.0864(10) Uani 1 1 d . . .
F15 F 0.51100(16) 1.0244(4) 0.38445(18) 0.0885(9) Uani 1 1 d . . .
F16 F 0.39538(18) 1.5051(5) 0.3850(2) 0.1068(11) Uani 1 1 d . . .
F17 F 0.38353(14) 1.2843(6) 0.29604(14) 0.1030(12) Uani 1 1 d . . .
F18 F 0.34255(15) 1.1849(5) 0.47321(14) 0.0848(9) Uani 1 1 d . . .
F19 F 0.32229(19) 0.9848(5) 0.3826(2) 0.1108(11) Uani 1 1 d . . .
F20 F 0.24219(15) 1.2643(5) 0.37857(16) 0.0969(11) Uani 1 1 d . . .
H1 H 1.044(2) 1.335(5) 0.482(2) 0.039(11) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 N2 1.318(4) . ?
C3 C3A 1.421(5) . ?
C3 C8 1.506(4) . ?
C3A C4 1.402(5) . ?
C3A C7A 1.409(4) . ?
C4 F4 1.331(3) . ?
C4 C5 1.362(5) . ?
C5 F5 1.341(4) . ?
C5 C6 1.401(5) . ?
C6 C7 1.342(5) . ?
C6 F6 1.350(4) . ?
C7 F7 1.349(3) . ?
C7 C7A 1.394(4) . ?
C7A N1 1.351(4) . ?
C8 F8 1.343(4) . ?
C8 F9 1.343(4) . ?
C8 C9 1.545(4) . ?
C9 F11 1.338(4) . ?
C9 F10 1.339(4) . ?
C9 C10 1.557(4) . ?
C10 F12 1.326(4) . ?
C10 F13 1.330(4) . ?
C10 C11 1.543(5) . ?
C11 F14 1.314(4) . ?
C11 F15 1.331(4) . ?
C11 C12 1.534(5) . ?
C12 F17 1.309(4) . ?
C12 F16 1.332(5) . ?
C12 C13 1.525(5) . ?
C13 F18 1.271(4) . ?
C13 F20 1.289(4) . ?
C13 F19 1.335(5) . ?
N1 N2 1.360(3) . ?
N1 H1 0.79(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
N2 C3 C3A 111.6(3) . . ?
N2 C3 C8 119.5(3) . . ?
C3A C3 C8 128.9(3) . . ?
C4 C3A C7A 118.1(3) . . ?
C4 C3A C3 138.1(3) . . ?
C7A C3A C3 103.8(3) . . ?
F4 C4 C5 120.0(3) . . ?
F4 C4 C3A 120.9(3) . . ?
C5 C4 C3A 119.1(3) . . ?
F5 C5 C4 120.1(3) . . ?
F5 C5 C6 118.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
C7 C6 F6 120.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
F6 C6 C5 117.5(3) . . ?
C6 C7 F7 122.4(3) . . ?
C6 C7 C7A 118.0(3) . . ?
F7 C7 C7A 119.6(3) . . ?
N1 C7A C7 131.3(3) . . ?
N1 C7A C3A 106.7(3) . . ?
C7 C7A C3A 122.0(3) . . ?
F8 C8 F9 108.0(3) . . ?
F8 C8 C3 109.8(3) . . ?
F9 C8 C3 109.4(3) . . ?
F8 C8 C9 107.9(3) . . ?
F9 C8 C9 109.2(2) . . ?
C3 C8 C9 112.4(3) . . ?
F11 C9 F10 108.0(3) . . ?
F11 C9 C8 108.3(3) . . ?
F10 C9 C8 107.1(3) . . ?
F11 C9 C10 108.2(3) . . ?
F10 C9 C10 108.8(3) . . ?
C8 C9 C10 116.1(3) . . ?
F12 C10 F13 108.7(3) . . ?
F12 C10 C11 108.6(3) . . ?
F13 C10 C11 107.9(3) . . ?
F12 C10 C9 108.2(3) . . ?
F13 C10 C9 108.1(3) . . ?
C11 C10 C9 115.2(3) . . ?
F14 C11 F15 106.1(3) . . ?
F14 C11 C12 108.8(3) . . ?
F15 C11 C12 106.8(3) . . ?
F14 C11 C10 110.0(3) . . ?
F15 C11 C10 108.5(3) . . ?
C12 C11 C10 116.1(3) . . ?
F17 C12 F16 107.2(4) . . ?
F17 C12 C13 109.1(3) . . ?
F16 C12 C13 105.2(3) . . ?
F17 C12 C11 109.9(3) . . ?
F16 C12 C11 108.2(3) . . ?
C13 C12 C11 116.8(3) . . ?
F18 C13 F20 110.8(3) . . ?
F18 C13 F19 104.7(4) . . ?
F20 C13 F19 105.7(3) . . ?
F18 C13 C12 113.6(3) . . ?
F20 C13 C12 111.9(3) . . ?
F19 C13 C12 109.5(4) . . ?
C7A N1 N2 111.9(3) . . ?
C7A N1 H1 133(3) . . ?
N2 N1 H1 115(3) . . ?
C3 N2 N1 105.9(3) . . ?
_database_code_depnum_ccdc_archive 'CCDC 982669'
#######################################################################
#
#                 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_8

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C30 H B F33 N6 Tl), C H2 Cl2 '
_chemical_formula_sum            'C61 H4 B2 Cl2 F66 N12 Tl2'
_chemical_formula_weight         2660.04
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1 '
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7490(12)
_cell_length_b                   13.0300(11)
_cell_length_c                   14.4090(13)
_cell_angle_alpha                97.161(4)
_cell_angle_beta                 114.950(4)
_cell_angle_gamma                111.090(4)
_cell_volume                     1913.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8834
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      22.82
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    2.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1254
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.962

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_number            28371
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_reflns_number_total             7287
_reflns_number_gt                5562
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0656P)²+0.3029P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7287
_refine_ls_number_parameters     658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.038
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.887
_refine_diff_density_min         -1.458
_refine_diff_density_rms         0.23

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1963(12) 0.2735(9) 0.2368(9) 0.068(3) Uani 1 1 d . . .
C2 C 0.2890(9) 0.4032(7) 0.2756(7) 0.043(2) Uani 1 1 d . . .
C3 C 0.3543(8) 0.4402(6) 0.2100(6) 0.0366(19) Uani 1 1 d . . .
C4 C 0.4599(7) 0.5644(6) 0.2589(6) 0.0295(16) Uani 1 1 d . . .
C5 C 0.5935(7) 0.6111(6) 0.3381(6) 0.0285(16) Uani 1 1 d . . .
C6 C 0.6457(7) 0.7308(6) 0.3490(5) 0.0262(15) Uani 1 1 d . . .
C7 C 0.7793(7) 0.8060(7) 0.4212(6) 0.0355(18) Uani 1 1 d . . .
C8 C 0.8539(8) 0.7604(9) 0.4805(7) 0.048(2) Uani 1 1 d . . .
C9 C 0.8023(9) 0.6417(9) 0.4704(7) 0.051(2) Uani 1 1 d . . .
C10 C 0.6743(9) 0.5666(7) 0.4007(7) 0.042(2) Uani 1 1 d . . .
C11 C 0.0867(8) 0.5121(7) -0.2998(7) 0.044(2) Uani 1 1 d . . .
C12 C 0.2073(7) 0.5866(7) -0.1894(6) 0.0353(18) Uani 1 1 d . . .
C13 C 0.2265(7) 0.7079(6) -0.1368(6) 0.0329(18) Uani 1 1 d . . .
C14 C 0.3554(7) 0.7793(6) -0.0370(5) 0.0270(16) Uani 1 1 d . . .
C15 C 0.4765(7) 0.8502(6) -0.0271(5) 0.0255(15) Uani 1 1 d . . .
C16 C 0.5663(7) 0.8932(5) 0.0853(5) 0.0222(14) Uani 1 1 d . . .
C17 C 0.6980(7) 0.9673(6) 0.1261(6) 0.0272(16) Uani 1 1 d . . .
C18 C 0.7360(8) 0.9959(7) 0.0550(7) 0.0363(19) Uani 1 1 d . . .
C19 C 0.6474(8) 0.9536(7) -0.0573(7) 0.0363(19) Uani 1 1 d . . .
C20 C 0.5204(8) 0.8814(6) -0.0977(6) 0.0360(19) Uani 1 1 d . . .
C21 C -0.0687(8) 0.8126(8) 0.1613(9) 0.052(3) Uani 1 1 d . . .
C22 C 0.0741(7) 0.8634(6) 0.1901(6) 0.0337(18) Uani 1 1 d . . .
C23 C 0.1669(7) 0.8419(6) 0.2854(6) 0.0319(17) Uani 1 1 d . . .
C24 C 0.3054(7) 0.8968(6) 0.3094(5) 0.0250(15) Uani 1 1 d . . .
C25 C 0.4048(7) 1.0129(6) 0.3721(5) 0.0256(15) Uani 1 1 d . . .
C26 C 0.5112(6) 1.0154(5) 0.3617(5) 0.0211(14) Uani 1 1 d . . .
C27 C 0.6306(7) 1.1187(6) 0.4119(5) 0.0274(16) Uani 1 1 d . . .
C28 C 0.6391(8) 1.2138(6) 0.4705(5) 0.0335(19) Uani 1 1 d . . .
C29 C 0.5336(8) 1.2117(6) 0.4823(6) 0.0351(19) Uani 1 1 d . . .
C30 C 0.4176(8) 1.1134(7) 0.4341(6) 0.0335(18) Uani 1 1 d . . .
N1 N 0.4328(6) 0.6472(5) 0.2264(5) 0.0274(13) Uani 1 1 d . . .
N2 N 0.5449(5) 0.7496(5) 0.2798(4) 0.0235(13) Uani 1 1 d . . .
N3 N 0.3699(5) 0.7783(4) 0.0599(4) 0.0230(12) Uani 1 1 d . . .
N4 N 0.4977(5) 0.8476(5) 0.1353(4) 0.0217(12) Uani 1 1 d . . .
N5 N 0.3456(5) 0.8363(5) 0.2655(5) 0.0265(13) Uani 1 1 d . . .
N6 N 0.4735(5) 0.9067(5) 0.2964(4) 0.0237(12) Uani 1 1 d . . .
F1 F 0.1381(7) 0.2519(6) 0.2939(5) 0.098(3) Uani 1 1 d . . .
F2 F 0.1103(7) 0.2379(6) 0.1369(5) 0.112(3) Uani 1 1 d . . .
F3 F 0.2635(9) 0.2130(5) 0.2522(7) 0.116(3) Uani 1 1 d . . .
F4 F 0.3820(5) 0.4320(4) 0.3792(4) 0.0583(15) Uani 1 1 d . . .
F5 F 0.2239(6) 0.4634(5) 0.2751(5) 0.0618(14) Uani 1 1 d . . .
F6 F 0.4037(6) 0.3670(4) 0.1947(4) 0.0569(14) Uani 1 1 d . . .
F6B F 0.2589(5) 0.4248(4) 0.1105(3) 0.0467(13) Uani 1 1 d . . .
F7 F 0.8321(4) 0.9196(4) 0.4353(4) 0.0495(13) Uani 1 1 d . . .
F8 F 0.9801(5) 0.8290(5) 0.5511(5) 0.0717(17) Uani 1 1 d . . .
F9 F 0.8824(6) 0.6034(6) 0.5325(5) 0.0753(18) Uani 1 1 d . . .
F10 F 0.6264(6) 0.4533(4) 0.3922(4) 0.0596(15) Uani 1 1 d . . .
F11 F 0.0791(5) 0.4064(4) -0.3266(4) 0.0585(14) Uani 1 1 d . . .
F12 F -0.0164(5) 0.5021(5) -0.2966(4) 0.0628(15) Uani 1 1 d . . .
F13 F 0.0953(6) 0.5600(5) -0.3733(4) 0.0607(15) Uani 1 1 d . . .
F14 F 0.3137(4) 0.6030(4) -0.1999(4) 0.0442(11) Uani 1 1 d . . .
F15 F 0.2066(5) 0.5255(4) -0.1197(4) 0.0484(13) Uani 1 1 d . . .
F16 F 0.1295(4) 0.6868(4) -0.1114(3) 0.0428(11) Uani 1 1 d . . .
F16B F 0.2053(5) 0.7615(4) -0.2104(3) 0.0469(12) Uani 1 1 d . . .
F17 F 0.7865(4) 1.0101(4) 0.2312(3) 0.0385(11) Uani 1 1 d . . .
F18 F 0.8605(4) 1.0665(4) 0.0892(4) 0.0486(12) Uani 1 1 d . . .
F19 F 0.6921(5) 0.9848(5) -0.1247(4) 0.0566(14) Uani 1 1 d . . .
F20 F 0.4376(5) 0.8417(4) -0.2052(3) 0.0519(13) Uani 1 1 d . . .
F21 F -0.0802(6) 0.8563(8) 0.2401(6) 0.108(3) Uani 1 1 d . . .
F22 F -0.1370(5) 0.8351(5) 0.0766(5) 0.0717(18) Uani 1 1 d . . .
F23 F -0.1183(5) 0.6996(5) 0.1364(6) 0.089(2) Uani 1 1 d . . .
F24 F 0.1183(5) 0.9783(4) 0.2094(4) 0.0503(13) Uani 1 1 d . . .
F25 F 0.0748(5) 0.8181(4) 0.1003(4) 0.0492(12) Uani 1 1 d . . .
F26 F 0.1223(4) 0.7239(4) 0.2598(4) 0.0421(11) Uani 1 1 d . . .
F26B F 0.1592(5) 0.8782(5) 0.3721(4) 0.0545(13) Uani 1 1 d . . .
F27 F 0.7320(4) 1.1257(3) 0.4035(3) 0.0364(10) Uani 1 1 d . . .
F28 F 0.7481(5) 1.3145(4) 0.5200(4) 0.0478(12) Uani 1 1 d . . .
F29 F 0.5490(5) 1.3099(4) 0.5419(4) 0.0532(13) Uani 1 1 d . . .
F30 F 0.3193(5) 1.1134(4) 0.4451(4) 0.0481(12) Uani 1 1 d . . .
Tl1 Tl 0.19792(3) 0.63173(2) 0.10437(2) 0.03374(12) Uani 1 1 d . . .
B1 B 0.5503(8) 0.8665(7) 0.2574(6) 0.0270(18) Uani 1 1 d . . .
H1 H 0.6432 0.9278 0.2983 0.032 Uiso 1 1 calc R . .
Cl1 Cl -0.4344(3) 0.6244(3) 0.0590(3) 0.1009(12) Uani 1 1 d . . .
C101 C -0.467(3) 0.515(2) -0.028(2) 0.085(8) Uani 0.5 1 d P . -1
H10A H -0.3822 0.5179 -0.011 0.102 Uiso 0.5 1 calc PR . -1
H10B H -0.4997 0.5313 -0.0976 0.102 Uiso 0.5 1 calc PR . -1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.274(12) . ?
C1 F1 1.315(13) . ?
C1 F3 1.333(15) . ?
C1 C2 1.528(12) . ?
C2 F5 1.331(11) . ?
C2 F4 1.350(9) . ?
C2 C3 1.518(12) . ?
C3 F6 1.361(10) . ?
C3 F6B 1.362(9) . ?
C3 C4 1.509(10) . ?
C4 N1 1.327(9) . ?
C4 C5 1.419(11) . ?
C5 C10 1.410(11) . ?
C5 C6 1.415(10) . ?
C6 N2 1.382(9) . ?
C6 C7 1.412(10) . ?
C7 F7 1.334(9) . ?
C7 C8 1.355(11) . ?
C8 F8 1.334(10) . ?
C8 C9 1.405(13) . ?
C9 F9 1.342(9) . ?
C9 C10 1.361(13) . ?
C10 F10 1.345(9) . ?
C11 F12 1.295(11) . ?
C11 F13 1.317(10) . ?
C11 F11 1.340(10) . ?
C11 C12 1.522(11) . ?
C12 F15 1.358(8) . ?
C12 F14 1.372(9) . ?
C12 C13 1.549(11) . ?
C13 F16B 1.328(8) . ?
C13 F16 1.379(9) . ?
C13 C14 1.485(10) . ?
C14 N3 1.332(9) . ?
C14 C15 1.419(10) . ?
C15 C20 1.390(10) . ?
C15 C16 1.413(10) . ?
C16 N4 1.379(9) . ?
C16 C17 1.399(10) . ?
C17 F17 1.332(8) . ?
C17 C18 1.344(11) . ?
C18 F18 1.337(9) . ?
C18 C19 1.409(12) . ?
C19 C20 1.349(11) . ?
C19 F19 1.352(8) . ?
C20 F20 1.344(9) . ?
C21 F21 1.294(13) . ?
C21 F23 1.305(10) . ?
C21 F22 1.307(11) . ?
C21 C22 1.534(11) . ?
C22 F24 1.339(8) . ?
C22 F25 1.358(9) . ?
C22 C23 1.526(10) . ?
C23 F26B 1.336(9) . ?
C23 F26 1.369(8) . ?
C23 C24 1.505(10) . ?
C24 N5 1.312(9) . ?
C24 C25 1.423(10) . ?
C25 C30 1.403(10) . ?
C25 C26 1.416(10) . ?
C26 N6 1.385(8) . ?
C26 C27 1.417(9) . ?
C27 F27 1.320(8) . ?
C27 C28 1.351(10) . ?
C28 F28 1.334(8) . ?
C28 C29 1.416(12) . ?
C29 F29 1.347(8) . ?
C29 C30 1.363(11) . ?
C30 F30 1.329(9) . ?
N1 N2 1.363(8) . ?
N1 Tl1 2.671(6) . ?
N2 B1 1.580(10) . ?
N3 N4 1.362(7) . ?
N3 Tl1 2.709(5) . ?
N4 B1 1.543(9) . ?
N5 N6 1.382(8) . ?
N5 Tl1 2.683(6) . ?
N6 B1 1.520(11) . ?
B1 H1 1 . ?
Cl1 C101 1.57(2) . ?
Cl1 C101 1.66(2) 2_465 ?
C101 Cl1 1.66(2) 2_465 ?
C101 H10A 0.99 . ?
C101 H10B 0.99 . ?

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 F1 109.1(10) . . ?
F2 C1 F3 109.6(11) . . ?
F1 C1 F3 106.4(9) . . ?
F2 C1 C2 111.3(8) . . ?
F1 C1 C2 110.7(9) . . ?
F3 C1 C2 109.6(10) . . ?
F5 C2 F4 107.5(7) . . ?
F5 C2 C3 108.2(7) . . ?
F4 C2 C3 108.8(7) . . ?
F5 C2 C1 108.9(8) . . ?
F4 C2 C1 107.7(7) . . ?
C3 C2 C1 115.6(8) . . ?
F6 C3 F6B 106.9(6) . . ?
F6 C3 C4 109.6(7) . . ?
F6B C3 C4 109.5(6) . . ?
F6 C3 C2 109.1(6) . . ?
F6B C3 C2 106.8(7) . . ?
C4 C3 C2 114.6(7) . . ?
N1 C4 C5 110.8(6) . . ?
N1 C4 C3 119.9(7) . . ?
C5 C4 C3 129.4(7) . . ?
C10 C5 C6 120.2(7) . . ?
C10 C5 C4 135.6(7) . . ?
C6 C5 C4 104.2(6) . . ?
N2 C6 C7 132.3(6) . . ?
N2 C6 C5 107.4(6) . . ?
C7 C6 C5 120.3(6) . . ?
F7 C7 C8 119.7(7) . . ?
F7 C7 C6 122.3(6) . . ?
C8 C7 C6 117.9(8) . . ?
F8 C8 C7 119.8(8) . . ?
F8 C8 C9 118.3(7) . . ?
C7 C8 C9 121.9(8) . . ?
F9 C9 C10 120.0(9) . . ?
F9 C9 C8 118.3(8) . . ?
C10 C9 C8 121.7(7) . . ?
F10 C10 C9 120.9(7) . . ?
F10 C10 C5 121.1(8) . . ?
C9 C10 C5 118.0(8) . . ?
F12 C11 F13 110.1(7) . . ?
F12 C11 F11 109.5(7) . . ?
F13 C11 F11 108.6(7) . . ?
F12 C11 C12 109.9(7) . . ?
F13 C11 C12 109.7(7) . . ?
F11 C11 C12 109.1(7) . . ?
F15 C12 F14 107.6(6) . . ?
F15 C12 C11 108.2(6) . . ?
F14 C12 C11 107.4(7) . . ?
F15 C12 C13 108.0(6) . . ?
F14 C12 C13 107.6(6) . . ?
C11 C12 C13 117.7(7) . . ?
F16B C13 F16 107.3(6) . . ?
F16B C13 C14 112.2(6) . . ?
F16 C13 C14 109.5(6) . . ?
F16B C13 C12 108.9(6) . . ?
F16 C13 C12 105.7(6) . . ?
C14 C13 C12 113.0(6) . . ?
N3 C14 C15 110.5(6) . . ?
N3 C14 C13 120.6(6) . . ?
C15 C14 C13 128.8(6) . . ?
C20 C15 C16 119.4(7) . . ?
C20 C15 C14 136.1(7) . . ?
C16 C15 C14 104.5(6) . . ?
N4 C16 C17 132.1(6) . . ?
N4 C16 C15 107.1(6) . . ?
C17 C16 C15 120.8(6) . . ?
F17 C17 C18 119.0(6) . . ?
F17 C17 C16 123.1(6) . . ?
C18 C17 C16 117.9(7) . . ?
F18 C18 C17 120.6(7) . . ?
F18 C18 C19 117.5(7) . . ?
C17 C18 C19 121.9(7) . . ?
C20 C19 F19 120.2(7) . . ?
C20 C19 C18 120.8(7) . . ?
F19 C19 C18 119.0(7) . . ?
F20 C20 C19 119.8(7) . . ?
F20 C20 C15 120.9(7) . . ?
C19 C20 C15 119.3(7) . . ?
F21 C21 F23 110.3(9) . . ?
F21 C21 F22 107.6(8) . . ?
F23 C21 F22 107.3(8) . . ?
F21 C21 C22 111.5(8) . . ?
F23 C21 C22 109.5(8) . . ?
F22 C21 C22 110.6(8) . . ?
F24 C22 F25 107.8(6) . . ?
F24 C22 C23 109.0(6) . . ?
F25 C22 C23 108.3(6) . . ?
F24 C22 C21 107.1(7) . . ?
F25 C22 C21 106.8(7) . . ?
C23 C22 C21 117.5(7) . . ?
F26B C23 F26 107.3(6) . . ?
F26B C23 C24 111.2(6) . . ?
F26 C23 C24 108.5(6) . . ?
F26B C23 C22 108.6(6) . . ?
F26 C23 C22 107.1(6) . . ?
C24 C23 C22 113.9(6) . . ?
N5 C24 C25 111.5(6) . . ?
N5 C24 C23 119.6(6) . . ?
C25 C24 C23 128.8(7) . . ?
C30 C25 C26 119.9(7) . . ?
C30 C25 C24 136.7(7) . . ?
C26 C25 C24 103.4(6) . . ?
N6 C26 C25 108.6(6) . . ?
N6 C26 C27 130.4(6) . . ?
C25 C26 C27 120.9(6) . . ?
F27 C27 C28 119.4(6) . . ?
F27 C27 C26 123.1(6) . . ?
C28 C27 C26 117.5(7) . . ?
F28 C28 C27 121.1(7) . . ?
F28 C28 C29 116.9(7) . . ?
C27 C28 C29 122.0(7) . . ?
F29 C29 C30 119.8(8) . . ?
F29 C29 C28 118.7(7) . . ?
C30 C29 C28 121.5(7) . . ?
F30 C30 C29 120.6(7) . . ?
F30 C30 C25 121.1(7) . . ?
C29 C30 C25 118.3(7) . . ?
C4 N1 N2 108.1(6) . . ?
C4 N1 Tl1 127.5(5) . . ?
N2 N1 Tl1 123.7(4) . . ?
N1 N2 C6 109.4(5) . . ?
N1 N2 B1 122.1(5) . . ?
C6 N2 B1 128.4(6) . . ?
C14 N3 N4 107.8(5) . . ?
C14 N3 Tl1 127.7(4) . . ?
N4 N3 Tl1 123.2(4) . . ?
N3 N4 C16 110.0(5) . . ?
N3 N4 B1 122.1(5) . . ?
C16 N4 B1 128.0(6) . . ?
C24 N5 N6 108.6(6) . . ?
C24 N5 Tl1 127.1(5) . . ?
N6 N5 Tl1 122.6(4) . . ?
N5 N6 C26 107.9(6) . . ?
N5 N6 B1 123.1(6) . . ?
C26 N6 B1 129.0(6) . . ?
N1 Tl1 N5 71.48(18) . . ?
N1 Tl1 N3 70.72(16) . . ?
N5 Tl1 N3 71.10(17) . . ?
N6 B1 N4 111.4(6) . . ?
N6 B1 N2 110.4(6) . . ?
N4 B1 N2 109.3(6) . . ?
N6 B1 H1 108.6 . . ?
N4 B1 H1 108.6 . . ?
N2 B1 H1 108.6 . . ?
C101 Cl1 C101 50.8(15) . 2_465 ?
Cl1 C101 Cl1 129.2(15) . 2_465 ?
Cl1 C101 H10A 105 . . ?
Cl1 C101 H10A 105 2_465 . ?
Cl1 C101 H10B 105 . . ?
Cl1 C101 H10B 105 2_465 . ?
H10A C101 H10B 105.9 . . ?

#===END

_database_code_depnum_ccdc_archive 'CCDC 982670'
