# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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
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#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_(1)emimtdi
_audit_creation_date             2013-02-09
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_systematic        
'1-Ethyl-3-methylimidazolium 4,5-dicyano-2-(trifluoromethyl)imidazole'
_chemical_name_common            EMImTDI
_chemical_formula_moiety         'C6 F3 N4, C6 H11 N2'
_chemical_formula_sum            'C12 H11 F3 N6'
_chemical_formula_weight         296.27
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'

_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.0(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a                   8.63283(15)
_cell_length_b                   8.86281(12)
_cell_length_c                   10.25772(13)
_cell_angle_alpha                87.4723(11)
_cell_angle_beta                 78.8034(13)
_cell_angle_gamma                66.0794(15)
_cell_volume                     703.24(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    52242
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.7618
_cell_measurement_theta_min      3.6105
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0055
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            111869
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         3.62
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9790
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -66.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  150.0000  160.5894 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   10.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -57.0000 -120.0000 126

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00  -16.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  148.0000  -56.8500 152

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   56.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   38.0000  -60.0000 204

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   50.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   38.0000 -180.0000 164

#__ type_ start__ end____ width___ exp.time_
  6 omega  -99.00    6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -77.0000 -180.0000 210

#__ type_ start__ end____ width___ exp.time_
  7 omega  -99.00   14.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -77.0000   30.0000 226

#__ type_ start__ end____ width___ exp.time_
  8 omega  -61.00   43.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -19.0000   30.0000 208

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   62.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -99.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega  -96.00    7.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -38.0000  -30.0000 206

#__ type_ start__ end____ width___ exp.time_
 11 omega  -46.00   56.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071   38.0000 -180.0000 204

#__ type_ start__ end____ width___ exp.time_
 12 omega  -96.00    7.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -38.0000 -180.0000 206

#__ type_ start__ end____ width___ exp.time_
 13 omega -109.00  -32.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  179.0000  -30.0000 154

#__ type_ start__ end____ width___ exp.time_
 14 omega -101.00   26.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -19.0000   60.0000 254

#__ type_ start__ end____ width___ exp.time_
 15 omega   56.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  179.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
 16 omega   53.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196 -179.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 17 omega  -94.00   10.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  -57.0000   30.0000 208

#__ type_ start__ end____ width___ exp.time_
 18 omega  -79.00    1.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071  128.0000  -19.3753 160

#__ type_ start__ end____ width___ exp.time_
 19 omega   -4.00   62.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -99.0000 -180.0000 132

#__ type_ start__ end____ width___ exp.time_
 20 omega   56.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  179.0000    0.0000 108

#__ type_ start__ end____ width___ exp.time_
 21 omega   -6.00   96.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196   38.0000  -30.0000 204

#__ type_ start__ end____ width___ exp.time_
 22 omega   -9.00   94.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196   57.0000   60.0000 206

#__ type_ start__ end____ width___ exp.time_
 23 omega   -4.00   62.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196  -99.0000 -150.0000 132

#__ type_ start__ end____ width___ exp.time_
 24 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -150.0000 358

#__ type_ start__ end____ width___ exp.time_
 25 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -120.0000 358

#__ type_ start__ end____ width___ exp.time_
 26 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000  -90.0000 358

#__ type_ start__ end____ width___ exp.time_
 27 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000  -60.0000 358

#__ type_ start__ end____ width___ exp.time_
 28 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000  -30.0000 358

#__ type_ start__ end____ width___ exp.time_
 29 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000    0.0000 358

#__ type_ start__ end____ width___ exp.time_
 30 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000 -180.0000 358

#__ type_ start__ end____ width___ exp.time_
 31 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000 -180.0000 358

#__ type_ start__ end____ width___ exp.time_
 32 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000 -150.0000 358

#__ type_ start__ end____ width___ exp.time_
 33 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000   90.0000 358

#__ type_ start__ end____ width___ exp.time_
 34 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000  150.0000 358

#__ type_ start__ end____ width___ exp.time_
 35 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000  120.0000 358

#__ type_ start__ end____ width___ exp.time_
 36 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000   60.0000 358

#__ type_ start__ end____ width___ exp.time_
 37 omega  -69.00  110.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1196    0.0000   30.0000 358

#__ type_ start__ end____ width___ exp.time_
 38 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000  -90.0000 358

#__ type_ start__ end____ width___ exp.time_
 39 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000  -60.0000 358

#__ type_ start__ end____ width___ exp.time_
 40 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000  -30.0000 358

#__ type_ start__ end____ width___ exp.time_
 41 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000    0.0000 358

#__ type_ start__ end____ width___ exp.time_
 42 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000   30.0000 358

#__ type_ start__ end____ width___ exp.time_
 43 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000   60.0000 358

#__ type_ start__ end____ width___ exp.time_
 44 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000 -120.0000 358

#__ type_ start__ end____ width___ exp.time_
 45 omega -109.00  -38.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000  120.0000 142

#__ type_ start__ end____ width___ exp.time_
 46 omega -109.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8071    0.0000   90.0000 358
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0453512000
_diffrn_orient_matrix_UB_12      -0.0852772000
_diffrn_orient_matrix_UB_13      0.0097559000
_diffrn_orient_matrix_UB_21      -0.0765647000
_diffrn_orient_matrix_UB_22      -0.0125246000
_diffrn_orient_matrix_UB_23      0.0022396000
_diffrn_orient_matrix_UB_31      0.0217456000
_diffrn_orient_matrix_UB_32      -0.0157343000
_diffrn_orient_matrix_UB_33      -0.0698284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3740
_reflns_number_total             3902
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0562P)²+0.3044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1090
_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. 

_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, H10 of C10, H11 of C11, {H8a,H8b} of C8
 At 1.5 times of:
  {H12a,H12b,H12c} of C12, {H7a,H7b,H7c} of C7
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C12(H12a,H12b,H12c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.00807(8) 0.37302(8) 0.10442(7) 0.02864(16) Uani 1 1 d . . .
F2 F 0.85451(9) 0.23824(8) 0.17311(10) 0.0406(2) Uani 1 1 d . . .
F3 F 0.96211(10) 0.32512(11) 0.31156(7) 0.0443(2) Uani 1 1 d . . .
N1 N 0.65639(11) 0.59571(10) 0.34911(8) 0.01852(17) Uani 1 1 d . . .
N2 N 0.65065(10) 0.59185(10) 0.12641(8) 0.01673(16) Uani 1 1 d . . .
N3 N 0.28515(14) 0.92599(13) 0.06099(11) 0.0319(2) Uani 1 1 d . . .
N4 N 0.29757(15) 0.93283(13) 0.51025(11) 0.0357(2) Uani 1 1 d . . .
N5 N 0.95824(11) 0.28565(10) 0.76541(8) 0.01785(17) Uani 1 1 d . . .
N6 N 0.73288(10) 0.50029(10) 0.73531(8) 0.01619(16) Uani 1 1 d . . .
C1 C 0.88791(12) 0.36488(12) 0.20573(9) 0.01874(18) Uani 1 1 d . . .
C2 C 0.72929(12) 0.52254(11) 0.22795(9) 0.01588(17) Uani 1 1 d . . .
C3 C 0.51160(12) 0.72543(11) 0.18812(9) 0.01640(17) Uani 1 1 d . . .
C4 C 0.51493(12) 0.72750(11) 0.32390(9) 0.01785(18) Uani 1 1 d . . .
C5 C 0.39462(14) 0.84144(13) 0.42698(10) 0.0242(2) Uani 1 1 d . . .
C6 C 0.38668(13) 0.83742(12) 0.11770(10) 0.02120(19) Uani 1 1 d . . .
C7 C 0.60445(17) 0.80397(15) 0.7444(2) 0.0454(4) Uani 1 1 d . . .
H7A H 0.6681 0.8031 0.6541 0.068 Uiso 1 1 calc R . .
H7B H 0.6726 0.8087 0.8090 0.068 Uiso 1 1 calc R . .
H7C H 0.4940 0.9008 0.7587 0.068 Uiso 1 1 calc R . .
C8 C 0.57174(12) 0.65015(12) 0.76196(11) 0.02127(19) Uani 1 1 d . . .
H8A H 0.5105 0.6499 0.8541 0.026 Uiso 1 1 calc R . .
H8B H 0.4962 0.6496 0.7008 0.026 Uiso 1 1 calc R . .
C9 C 0.81844(12) 0.41219(11) 0.82682(9) 0.01678(18) Uani 1 1 d . . .
H9 H 0.7855 0.4355 0.9201 0.020 Uiso 1 1 calc R . .
C10 C 0.81968(14) 0.42911(13) 0.61128(9) 0.0220(2) Uani 1 1 d . . .
H10 H 0.7871 0.4671 0.5286 0.026 Uiso 1 1 calc R . .
C11 C 0.96128(14) 0.29367(13) 0.63012(10) 0.0229(2) Uani 1 1 d . . .
H11 H 1.0462 0.2188 0.5629 0.028 Uiso 1 1 calc R . .
C12 C 1.08760(14) 0.15780(12) 0.82997(11) 0.0237(2) Uani 1 1 d . . .
H12A H 1.1569 0.0637 0.7673 0.035 Uiso 1 1 calc R . .
H12B H 1.0290 0.1212 0.9084 0.035 Uiso 1 1 calc R . .
H12C H 1.1631 0.2034 0.8572 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 C1 1.3404(11) . ?
F2 C1 1.3372(12) . ?
F3 C1 1.3289(11) . ?
N1 C2 1.3408(12) . ?
N1 C4 1.3645(12) . ?
N2 C2 1.3427(11) . ?
N2 C3 1.3645(12) . ?
N3 C6 1.1500(14) . ?
N4 C5 1.1490(15) . ?
N5 C9 1.3343(12) . ?
N5 C11 1.3821(12) . ?
N5 C12 1.4713(12) . ?
N6 C8 1.4697(12) . ?
N6 C9 1.3316(11) . ?
N6 C10 1.3767(12) . ?
C1 C2 1.4949(13) . ?
C3 C4 1.3997(12) . ?
C3 C6 1.4287(13) . ?
C4 C5 1.4261(13) . ?
C7 C8 1.4971(16) . ?
C10 C11 1.3615(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 101.95(8) . . ?
C2 N2 C3 101.98(8) . . ?
C9 N5 C11 108.57(8) . . ?
C9 N5 C12 126.09(8) . . ?
C11 N5 C12 125.34(8) . . ?
C9 N6 C8 125.57(8) . . ?
C9 N6 C10 109.18(8) . . ?
C10 N6 C8 125.24(8) . . ?
F1 C1 C2 111.98(8) . . ?
F2 C1 F1 105.26(8) . . ?
F2 C1 C2 111.90(8) . . ?
F3 C1 F1 106.62(8) . . ?
F3 C1 F2 108.15(9) . . ?
F3 C1 C2 112.51(8) . . ?
N1 C2 N2 117.70(8) . . ?
N1 C2 C1 121.90(8) . . ?
N2 C2 C1 120.34(8) . . ?
N2 C3 C4 109.13(8) . . ?
N2 C3 C6 122.15(8) . . ?
C4 C3 C6 128.71(9) . . ?
N1 C4 C3 109.25(8) . . ?
N1 C4 C5 121.85(9) . . ?
C3 C4 C5 128.90(9) . . ?
N4 C5 C4 179.78(14) . . ?
N3 C6 C3 179.05(11) . . ?
N6 C8 C7 111.92(9) . . ?
N6 C9 N5 108.46(8) . . ?
C11 C10 N6 106.69(8) . . ?
C10 C11 N5 107.10(8) . . ?

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
C9 H9 N2 0.95 2.40 3.3031(12) 159.2 1_556
C10 H10 F3 0.95 2.49 3.1108(12) 122.6 .
C10 H10 N1 0.95 2.35 3.2915(13) 169.0 .
C11 H11 N4 0.95 2.57 3.4058(14) 146.2 1_645

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
F1 C1 C2 N1 -131.44(10) . . . . ?
F1 C1 C2 N2 51.48(12) . . . . ?
F2 C1 C2 N1 110.66(11) . . . . ?
F2 C1 C2 N2 -66.43(12) . . . . ?
F3 C1 C2 N1 -11.35(14) . . . . ?
F3 C1 C2 N2 171.56(9) . . . . ?
N2 C3 C4 N1 0.24(11) . . . . ?
N2 C3 C4 C5 -178.64(10) . . . . ?
N6 C10 C11 N5 -0.31(12) . . . . ?
C2 N1 C4 C3 -0.04(10) . . . . ?
C2 N1 C4 C5 178.93(9) . . . . ?
C2 N2 C3 C4 -0.32(10) . . . . ?
C2 N2 C3 C6 -179.20(9) . . . . ?
C3 N2 C2 N1 0.33(11) . . . . ?
C3 N2 C2 C1 177.53(8) . . . . ?
C4 N1 C2 N2 -0.19(11) . . . . ?
C4 N1 C2 C1 -177.34(9) . . . . ?
C6 C3 C4 N1 179.02(9) . . . . ?
C6 C3 C4 C5 0.15(18) . . . . ?
C8 N6 C9 N5 -179.87(8) . . . . ?
C8 N6 C10 C11 -179.97(9) . . . . ?
C9 N5 C11 C10 0.25(12) . . . . ?
C9 N6 C8 C7 97.04(13) . . . . ?
C9 N6 C10 C11 0.26(12) . . . . ?
C10 N6 C8 C7 -82.69(14) . . . . ?
C10 N6 C9 N5 -0.10(11) . . . . ?
C11 N5 C9 N6 -0.09(11) . . . . ?
C12 N5 C9 N6 -179.73(9) . . . . ?
C12 N5 C11 C10 179.89(9) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 940806'
#######################################################################
#
#                 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)pmimlitdi
_audit_creation_date             2012-05-27
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_systematic        ?
_chemical_name_common            PMImLiTDI
_chemical_formula_moiety         'C12 F6 Li N8, C7 H13 N2'
_chemical_formula_sum            'C19 H13 F6 Li N10'
_chemical_formula_weight         502.33
_chemical_melting_point          ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.0
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.28368(13)
_cell_length_b                   11.45842(18)
_cell_length_c                   12.57923(20)
_cell_angle_alpha                74.9663(14)
_cell_angle_beta                 77.5238(13)
_cell_angle_gamma                78.6965(13)
_cell_volume                     1113.43(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    35212
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.5607
_cell_measurement_theta_min      3.6919
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            60286
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         3.69
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega   15.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  -38.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega   62.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   38.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   11.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   59.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   12.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega    8.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   38.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   -2.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372 -125.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega   12.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega    9.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 14 omega  -70.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  -71.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -71.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  -70.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -76.0000  -51.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega  -70.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -79.0000  153.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega -150.00 -123.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -73.0000   83.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega  -69.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  -68.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  -70.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -75.0000  -27.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega -115.00  -90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  130.0000 -179.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  -72.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -69.0000 -148.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega  -69.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -113.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega  -69.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  -70.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -72.0000  -89.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  -70.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -73.0000   83.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega  -69.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  -71.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   28.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 32 omega   59.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  120.0000 111

#__ type_ start__ end____ width___ exp.time_
 33 omega   59.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 34 omega   18.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 35 omega   60.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  119.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 37 omega   59.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 38 omega   61.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
 39 omega  130.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 40 omega   88.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 41 omega   60.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 42 omega   65.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -88.0000  -80.0000 39

#__ type_ start__ end____ width___ exp.time_
 43 omega   60.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   40.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
 45 omega  132.00  159.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 46 omega   60.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
 47 omega    8.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -88.0000  -80.0000 27

#__ type_ start__ end____ width___ exp.time_
 48 omega   89.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -15.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 49 omega   32.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 50 omega   94.00  128.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 51 omega  151.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 52 omega   11.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega   36.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -15.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 54 omega   10.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -15.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 55 omega  130.00  161.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  130.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 56 omega   92.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 57 omega  113.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 58 omega  114.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 59 omega   70.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -92.0000 -148.0000 50

#__ type_ start__ end____ width___ exp.time_
 60 omega   59.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 61 omega  100.00  154.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
 62 omega   30.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 63 omega   77.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 64 omega   60.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 65 omega   59.00  136.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
 66 omega   21.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
 67 omega   54.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 68 omega   22.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000 -120.0000 99

#__ type_ start__ end____ width___ exp.time_
 69 omega   97.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 70 omega   60.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 71 omega  133.00  160.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 72 omega   81.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 73 omega  146.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 74 omega   92.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 75 omega   21.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 76 omega   58.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 77 omega   21.00   48.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 78 omega   60.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 79 omega   66.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 80 omega   49.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 81 omega   75.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 82 omega  130.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 83 omega   61.00  135.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 84 omega -115.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -57.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
 85 omega  -98.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 86 omega -120.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 87 omega  -75.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372   77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 88 omega  -75.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372   77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 89 omega  -48.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000 -150.0000 178

#__ type_ start__ end____ width___ exp.time_
 90 omega  -48.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000 -180.0000 178

#__ type_ start__ end____ width___ exp.time_
 91 omega   11.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 92 omega    7.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 93 omega  -35.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  -38.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
 94 omega   64.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  140.0000   64.0000 51

#__ type_ start__ end____ width___ exp.time_
 95 omega   15.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   38.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
 96 omega  -38.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  -77.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
 97 omega -156.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -113.0000 113

#__ type_ start__ end____ width___ exp.time_
 98 omega -153.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -71.0000   69.0000 108

#__ type_ start__ end____ width___ exp.time_
 99 omega -152.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -68.0000  146.0000 107

#__ type_ start__ end____ width___ exp.time_
100 omega -153.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -71.0000  -55.0000 108

#__ type_ start__ end____ width___ exp.time_
101 omega -155.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -75.0000  -27.0000 111

#__ type_ start__ end____ width___ exp.time_
102 omega -155.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -76.0000  -12.0000 111

#__ type_ start__ end____ width___ exp.time_
103 omega -156.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
104 omega -153.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -71.0000   37.0000 108

#__ type_ start__ end____ width___ exp.time_
105 omega -153.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -70.0000   91.0000 108

#__ type_ start__ end____ width___ exp.time_
106 omega -153.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -69.0000 -178.0000 108

#__ type_ start__ end____ width___ exp.time_
107 omega   18.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
108 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
109 omega   15.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
110 omega   18.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
111 omega   14.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
112 omega   62.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
113 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
114 omega   65.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
115 omega   18.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
116 omega   62.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
117 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
118 omega   62.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000 -150.0000 108

#__ type_ start__ end____ width___ exp.time_
119 omega   65.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
120 omega   70.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  130.0000   71.0000 97

#__ type_ start__ end____ width___ exp.time_
121 omega    8.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -92.0000 -148.0000 124

#__ type_ start__ end____ width___ exp.time_
122 omega   18.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
123 omega   14.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
124 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
125 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
126 omega   62.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
127 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
128 omega   14.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
129 omega   65.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
130 omega   18.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
131 omega   59.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
132 omega   15.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  120.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0024727000
_diffrn_orient_matrix_UB_12      -0.1047309000
_diffrn_orient_matrix_UB_13      0.1053308000
_diffrn_orient_matrix_UB_21      -0.0508885000
_diffrn_orient_matrix_UB_22      0.0939069000
_diffrn_orient_matrix_UB_23      0.0739656000
_diffrn_orient_matrix_UB_31      -0.1857465000
_diffrn_orient_matrix_UB_32      -0.0054544000
_diffrn_orient_matrix_UB_33      0.0044315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3779
_reflns_number_total             3923
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.4509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0711
_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.

 Comments on remaining CHECKCIF errors:
 Hirshfield test violations for atoms C2-C5, C8-C11 and N7 are caused by
 out-of-plane bending vibrations of cyano groups.

;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.40736(9) 0.89843(6) 0.18475(6) 0.02429(16) Uani 1 1 d . . .
F2 F 0.66713(9) 0.89327(6) 0.10942(6) 0.02599(17) Uani 1 1 d . . .
F3 F 0.48989(10) 0.87050(6) 0.01697(6) 0.03043(18) Uani 1 1 d . . .
F4 F 0.65509(8) -0.06232(6) 0.63472(6) 0.02724(17) Uani 1 1 d . . .
F5 F 0.48903(9) -0.19193(6) 0.65276(6) 0.02606(17) Uani 1 1 d . . .
F6 F 0.49314(9) -0.11681(6) 0.79112(6) 0.02623(17) Uani 1 1 d . . .
N1 N 0.52839(11) 0.65946(8) 0.27473(8) 0.0166(2) Uani 1 1 d . . .
N2 N 0.62374(12) 0.63134(9) 0.09668(8) 0.0189(2) Uani 1 1 d . . .
N3 N 0.75780(15) 0.32354(10) 0.10121(9) 0.0307(3) Uani 1 1 d . . .
N4 N 0.58242(12) 0.36817(9) 0.45872(8) 0.0184(2) Uani 1 1 d . . .
N5 N 0.39573(12) 0.13081(9) 0.61261(8) 0.0165(2) Uani 1 1 d . . .
N6 N 0.21646(12) -0.00759(9) 0.64164(8) 0.0189(2) Uani 1 1 d . . .
N7 N -0.17611(12) 0.16254(9) 0.59196(8) 0.0211(2) Uani 1 1 d . . .
N8 N 0.17522(13) 0.42562(10) 0.52498(10) 0.0262(2) Uani 1 1 d . . .
N9 N 0.11943(12) 0.41002(10) 0.23050(8) 0.0226(2) Uani 1 1 d . . .
N10 N 0.08625(12) 0.23771(9) 0.20479(8) 0.0217(2) Uani 1 1 d . . .
C1 C 0.55822(14) 0.70795(10) 0.16430(9) 0.0174(2) Uani 1 1 d . . .
C2 C 0.63774(14) 0.52122(10) 0.17043(10) 0.0175(2) Uani 1 1 d . . .
C3 C 0.58038(13) 0.53773(10) 0.27888(9) 0.0160(2) Uani 1 1 d . . .
C4 C 0.70365(15) 0.41064(11) 0.13326(10) 0.0211(3) Uani 1 1 d . . .
C5 C 0.57879(13) 0.44547(10) 0.37993(9) 0.0163(2) Uani 1 1 d . . .
C6 C 0.52988(15) 0.84265(11) 0.11841(9) 0.0196(2) Uani 1 1 d . . .
C7 C 0.36886(14) 0.01358(10) 0.64221(9) 0.0166(2) Uani 1 1 d . . .
C8 C 0.13564(14) 0.10741(11) 0.60774(9) 0.0178(2) Uani 1 1 d . . .
C9 C 0.24409(14) 0.19159(10) 0.58999(9) 0.0170(2) Uani 1 1 d . . .
C10 C -0.03691(15) 0.13471(10) 0.59769(9) 0.0192(2) Uani 1 1 d . . .
C11 C 0.20836(14) 0.32135(11) 0.55378(10) 0.0193(2) Uani 1 1 d . . .
C12 C 0.50124(15) -0.08936(10) 0.68008(10) 0.0190(2) Uani 1 1 d . . .
C13 C 0.16604(15) 0.33353(11) 0.16199(10) 0.0230(3) Uani 1 1 d . . .
H13 H 0.2436 0.3457 0.0938 0.028 Uiso 1 1 calc R . .
C14 C -0.01543(15) 0.25266(11) 0.30415(10) 0.0218(3) Uani 1 1 d . . .
H14 H -0.0866 0.1977 0.3521 0.026 Uiso 1 1 calc R . .
C15 C 0.00537(15) 0.36046(12) 0.32044(10) 0.0223(3) Uani 1 1 d . . .
H15 H -0.0483 0.3955 0.3821 0.027 Uiso 1 1 calc R . .
C16 C 0.10044(17) 0.13407(12) 0.15358(11) 0.0280(3) Uani 1 1 d . . .
H16A H 0.1535 0.0600 0.1998 0.042 Uiso 1 1 calc R . .
H16B H 0.1685 0.1505 0.0787 0.042 Uiso 1 1 calc R . .
H16C H -0.0112 0.1224 0.1479 0.042 Uiso 1 1 calc R . .
C17 C 0.16924(16) 0.53147(12) 0.20979(11) 0.0265(3) Uani 1 1 d . . .
H17A H 0.2726 0.5362 0.1530 0.032 Uiso 1 1 calc R . .
H17B H 0.1941 0.5429 0.2796 0.032 Uiso 1 1 calc R . .
C18 C 0.03351(16) 0.63319(12) 0.16934(11) 0.0254(3) Uani 1 1 d . . .
H18A H -0.0694 0.6298 0.2266 0.030 Uiso 1 1 calc R . .
H18B H 0.0073 0.6215 0.1000 0.030 Uiso 1 1 calc R . .
C19 C 0.08938(18) 0.75752(12) 0.14676(11) 0.0300(3) Uani 1 1 d . . .
H19A H 0.1241 0.7663 0.2136 0.045 Uiso 1 1 calc R . .
H19B H -0.0036 0.8220 0.1279 0.045 Uiso 1 1 calc R . .
H19C H 0.1836 0.7643 0.0842 0.045 Uiso 1 1 calc R . .
Li1 Li 0.5766(2) 0.23544(17) 0.60327(16) 0.0186(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
F1 C6 1.3384(14) . ?
F2 C6 1.3457(14) . ?
F3 C6 1.3303(14) . ?
F4 C12 1.3397(14) . ?
F5 C12 1.3345(14) . ?
F6 C12 1.3396(14) . ?
N1 C1 1.3434(15) . ?
N1 C3 1.3676(15) . ?
N1 Li1 2.129(2) 2_666 ?
N2 C1 1.3378(15) . ?
N2 C2 1.3595(15) . ?
N3 C4 1.1467(16) . ?
N4 C5 1.1466(15) . ?
N4 Li1 2.044(2) . ?
N5 C7 1.3471(15) . ?
N5 C9 1.3611(15) . ?
N5 Li1 2.062(2) . ?
N6 C7 1.3332(15) . ?
N6 C8 1.3610(15) . ?
N7 C10 1.1473(16) . ?
N7 Li1 2.044(2) 1_455 ?
N8 C11 1.1506(16) . ?
N9 C13 1.3325(16) . ?
N9 C15 1.3822(16) . ?
N9 C17 1.4714(16) . ?
N10 C13 1.3253(17) . ?
N10 C14 1.3786(15) . ?
N10 C16 1.4658(16) . ?
C1 C6 1.4916(16) . ?
C2 C3 1.3932(16) . ?
C2 C4 1.4310(16) . ?
C3 C5 1.4264(16) . ?
C7 C12 1.4993(16) . ?
C8 C9 1.3888(16) . ?
C8 C10 1.4280(16) . ?
C9 C11 1.4284(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3518(18) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5190(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5219(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Li1 N1 2.129(2) 2_666 ?
Li1 N7 2.044(2) 1_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 101.87(9) . . ?
C1 N1 Li1 123.62(9) . 2_666 ?
C3 N1 Li1 134.50(9) . 2_666 ?
C1 N2 C2 102.12(9) . . ?
C5 N4 Li1 176.77(11) . . ?
C7 N5 C9 102.04(9) . . ?
C7 N5 Li1 140.77(9) . . ?
C9 N5 Li1 117.01(9) . . ?
C7 N6 C8 101.96(9) . . ?
C10 N7 Li1 167.96(11) . 1_455 ?
C13 N9 C15 108.44(10) . . ?
C13 N9 C17 125.97(10) . . ?
C15 N9 C17 125.39(10) . . ?
C13 N10 C14 108.91(10) . . ?
C13 N10 C16 125.61(10) . . ?
C14 N10 C16 125.46(10) . . ?
N1 C1 C6 121.63(10) . . ?
N2 C1 N1 117.50(10) . . ?
N2 C1 C6 120.75(10) . . ?
N2 C2 C3 109.48(10) . . ?
N2 C2 C4 121.29(10) . . ?
C3 C2 C4 129.24(11) . . ?
N1 C3 C2 109.02(10) . . ?
N1 C3 C5 124.09(10) . . ?
C2 C3 C5 126.86(10) . . ?
N3 C4 C2 178.49(13) . . ?
N4 C5 C3 177.11(12) . . ?
F1 C6 F2 106.58(9) . . ?
F1 C6 C1 111.42(9) . . ?
F2 C6 C1 111.72(9) . . ?
F3 C6 F1 108.06(9) . . ?
F3 C6 F2 106.90(9) . . ?
F3 C6 C1 111.88(10) . . ?
N5 C7 C12 121.85(10) . . ?
N6 C7 N5 117.35(10) . . ?
N6 C7 C12 120.73(10) . . ?
N6 C8 C9 109.69(10) . . ?
N6 C8 C10 123.93(10) . . ?
C9 C8 C10 126.32(11) . . ?
N5 C9 C8 108.96(10) . . ?
N5 C9 C11 123.75(10) . . ?
C8 C9 C11 127.29(10) . . ?
N7 C10 C8 176.03(12) . . ?
N8 C11 C9 178.20(12) . . ?
F4 C12 C7 111.65(9) . . ?
F5 C12 F4 107.33(9) . . ?
F5 C12 F6 106.42(9) . . ?
F5 C12 C7 112.03(10) . . ?
F6 C12 F4 106.54(9) . . ?
F6 C12 C7 112.50(9) . . ?
N9 C13 H13 125.7 . . ?
N10 C13 N9 108.64(10) . . ?
N10 C13 H13 125.7 . . ?
N10 C14 H14 126.5 . . ?
C15 C14 N10 106.95(11) . . ?
C15 C14 H14 126.5 . . ?
N9 C15 H15 126.5 . . ?
C14 C15 N9 107.05(11) . . ?
C14 C15 H15 126.5 . . ?
N10 C16 H16A 109.5 . . ?
N10 C16 H16B 109.5 . . ?
N10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N9 C17 H17A 109.2 . . ?
N9 C17 H17B 109.2 . . ?
N9 C17 C18 111.90(10) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 C19 110.79(11) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 Li1 N1 101.31(9) . 2_666 ?
N4 Li1 N5 108.89(9) . . ?
N5 Li1 N1 104.08(9) . 2_666 ?
N7 Li1 N1 118.13(10) 1_655 2_666 ?
N7 Li1 N4 100.75(9) 1_655 . ?
N7 Li1 N5 121.52(10) 1_655 . ?

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
C13 H13 N2 0.95 2.38 3.3059(15) 164.5 2_665
C16 H16A F1 0.98 2.52 3.3315(15) 139.6 1_545

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
N1 C1 C6 F1 -29.54(15) . . . . ?
N1 C1 C6 F2 89.55(13) . . . . ?
N1 C1 C6 F3 -150.64(10) . . . . ?
N2 C1 C6 F1 154.36(10) . . . . ?
N2 C1 C6 F2 -86.55(13) . . . . ?
N2 C1 C6 F3 33.26(15) . . . . ?
N2 C2 C3 N1 0.27(13) . . . . ?
N2 C2 C3 C5 -178.01(10) . . . . ?
N5 C7 C12 F4 -28.33(15) . . . . ?
N5 C7 C12 F5 -148.75(10) . . . . ?
N5 C7 C12 F6 91.41(13) . . . . ?
N6 C7 C12 F4 154.84(10) . . . . ?
N6 C7 C12 F5 34.42(15) . . . . ?
N6 C7 C12 F6 -85.42(13) . . . . ?
N6 C8 C9 N5 -0.06(13) . . . . ?
N6 C8 C9 C11 179.82(11) . . . . ?
N9 C17 C18 C19 -179.06(10) . . . . ?
N10 C14 C15 N9 0.12(13) . . . . ?
C1 N1 C3 C2 -0.12(12) . . . . ?
C1 N1 C3 C5 178.21(10) . . . . ?
C1 N2 C2 C3 -0.28(12) . . . . ?
C1 N2 C2 C4 179.88(11) . . . . ?
C2 N2 C1 N1 0.23(13) . . . . ?
C2 N2 C1 C6 176.49(10) . . . . ?
C3 N1 C1 N2 -0.07(13) . . . . ?
C3 N1 C1 C6 -176.30(10) . . . . ?
C4 C2 C3 N1 -179.91(11) . . . . ?
C4 C2 C3 C5 1.8(2) . . . . ?
C7 N5 C9 C8 0.22(12) . . . . ?
C7 N5 C9 C11 -179.67(11) . . . . ?
C7 N5 Li1 N1 -113.37(14) . . . 2_666 ?
C7 N5 Li1 N4 139.20(13) . . . . ?
C7 N5 Li1 N7 23.0(2) . . . 1_655 ?
C7 N6 C8 C9 -0.13(12) . . . . ?
C7 N6 C8 C10 -177.53(11) . . . . ?
C8 N6 C7 N5 0.30(13) . . . . ?
C8 N6 C7 C12 177.27(10) . . . . ?
C9 N5 C7 N6 -0.34(13) . . . . ?
C9 N5 C7 C12 -177.27(10) . . . . ?
C9 N5 Li1 N1 60.71(12) . . . 2_666 ?
C9 N5 Li1 N4 -46.73(13) . . . . ?
C9 N5 Li1 N7 -162.90(10) . . . 1_655 ?
C10 C8 C9 N5 177.26(11) . . . . ?
C10 C8 C9 C11 -2.85(19) . . . . ?
C13 N9 C15 C14 -0.08(13) . . . . ?
C13 N9 C17 C18 100.24(14) . . . . ?
C13 N10 C14 C15 -0.12(14) . . . . ?
C14 N10 C13 N9 0.07(14) . . . . ?
C15 N9 C13 N10 0.01(13) . . . . ?
C15 N9 C17 C18 -74.15(15) . . . . ?
C16 N10 C13 N9 178.66(11) . . . . ?
C16 N10 C14 C15 -178.71(11) . . . . ?
C17 N9 C13 N10 -175.18(11) . . . . ?
C17 N9 C15 C14 175.14(11) . . . . ?
Li1 N1 C1 N2 -179.59(10) 2_666 . . . ?
Li1 N1 C1 C6 4.18(16) 2_666 . . . ?
Li1 N1 C3 C2 179.32(10) 2_666 . . . ?
Li1 N1 C3 C5 -2.35(18) 2_666 . . . ?
Li1 N5 C7 N6 174.26(12) . . . . ?
Li1 N5 C7 C12 -2.7(2) . . . . ?
Li1 N5 C9 C8 -175.95(9) . . . . ?
Li1 N5 C9 C11 4.16(15) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 940807'
#######################################################################
#
#                 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)bmimlitdi
_audit_creation_date             2012-05-27
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_systematic        ?
_chemical_name_common            BMImLiTDI
_chemical_formula_moiety         'C12 F6 Li N8, C8 H15 N2'
_chemical_formula_sum            'C20 H15 F6 Li N10'
_chemical_properties_physical    moisture-sensitive
_chemical_formula_weight         516.36
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.42410(11)
_cell_length_b                   11.66815(17)
_cell_length_c                   12.85431(18)
_cell_angle_alpha                73.0547(13)
_cell_angle_beta                 74.4505(12)
_cell_angle_gamma                76.7560(12)
_cell_volume                     1148.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    55881
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      66.5857
_cell_measurement_theta_min      3.6787
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            80701
_diffrn_reflns_theta_full        66.70
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         3.68
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -22.0000  -89.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00  -94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   13.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega    8.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   79.0000 -148.0000 75

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   13.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega  -31.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  -57.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
 12 omega   92.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   79.0000 -148.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega  -68.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -79.0000  113.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -79.0000  148.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega  -70.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -79.0000    1.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega  -70.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -75.0000 -166.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  -70.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega  -70.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  -69.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -79.0000   87.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  -70.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -78.0000   55.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega  -70.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -73.0000    8.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega  -70.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega  -72.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -74.0000 -140.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega  116.00  142.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   64.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 30 omega   89.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 31 omega   61.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
 32 omega   16.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
 33 omega   64.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 34 omega   36.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 35 omega   19.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 36 omega   59.00  138.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
 37 omega  106.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 38 omega  115.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 39 omega   60.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 40 omega  139.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   63.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000 -146.0000 69

#__ type_ start__ end____ width___ exp.time_
 42 omega   59.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 43 omega   25.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  102.0000 85

#__ type_ start__ end____ width___ exp.time_
 44 omega   87.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 45 omega   63.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   61.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega  131.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 48 omega   19.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000 -146.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega   65.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 50 omega   60.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -120.0000 110

#__ type_ start__ end____ width___ exp.time_
 51 omega  126.00  161.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   79.0000  -87.0000 35

#__ type_ start__ end____ width___ exp.time_
 52 omega   60.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   79.0000  -87.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   69.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega  118.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 55 omega   93.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 56 omega   69.00  126.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
 57 omega   60.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 58 omega   60.00  146.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
 59 omega   65.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 60 omega  124.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 61 omega   18.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 62 omega   95.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 63 omega   32.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 64 omega   61.00  145.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 65 omega   17.00   60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 66 omega   60.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 67 omega  117.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 68 omega   45.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
 69 omega   21.00   47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 70 omega -120.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  -77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
 71 omega  -98.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
 72 omega  -98.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
 73 omega  -98.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 74 omega  -98.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372  125.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 75 omega  -87.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.0372   19.0000  120.0000 127

#__ type_ start__ end____ width___ exp.time_
 76 omega  -35.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372  -38.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 77 omega   15.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   38.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 78 omega    7.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 79 omega   15.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   38.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 80 omega   11.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372   57.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
 81 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
 82 omega -151.00  -48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -56.0000  -85.0000 103

#__ type_ start__ end____ width___ exp.time_
 83 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  128.0000 113

#__ type_ start__ end____ width___ exp.time_
 84 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
 85 omega -154.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -73.0000    8.0000 110

#__ type_ start__ end____ width___ exp.time_
 86 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 87 omega -153.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -70.0000  -87.0000 108

#__ type_ start__ end____ width___ exp.time_
 88 omega -154.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -73.0000  156.0000 110

#__ type_ start__ end____ width___ exp.time_
 89 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 90 omega -152.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -68.0000   20.0000 107

#__ type_ start__ end____ width___ exp.time_
 91 omega -152.00  -46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -67.0000 -117.0000 106

#__ type_ start__ end____ width___ exp.time_
 92 omega -153.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -71.0000  -28.0000 108

#__ type_ start__ end____ width___ exp.time_
 93 omega -155.00  -44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -75.0000 -166.0000 111

#__ type_ start__ end____ width___ exp.time_
 94 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 95 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 96 omega   65.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 97 omega   62.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  120.0000 108

#__ type_ start__ end____ width___ exp.time_
 98 omega   18.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 99 omega   14.00  126.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
100 omega   65.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
101 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
102 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
103 omega   62.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
104 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
105 omega   73.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
106 omega   62.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -90.0000 105

#__ type_ start__ end____ width___ exp.time_
107 omega   62.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
108 omega    8.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
109 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
110 omega    8.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  132.0000 124

#__ type_ start__ end____ width___ exp.time_
111 omega    9.00  154.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -15.0000  120.0000 145

#__ type_ start__ end____ width___ exp.time_
112 omega    8.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
113 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
114 omega   62.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000 -180.0000 108

#__ type_ start__ end____ width___ exp.time_
115 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
116 omega   65.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
117 omega   15.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
118 omega   18.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
119 omega   31.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 145

#__ type_ start__ end____ width___ exp.time_
120 omega   31.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000   30.0000 145

#__ type_ start__ end____ width___ exp.time_
121 omega   73.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
122 omega   18.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
123 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
124 omega    8.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
125 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000 -150.0000 178

#__ type_ start__ end____ width___ exp.time_
126 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000 -120.0000 178

#__ type_ start__ end____ width___ exp.time_
127 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000  -90.0000 178

#__ type_ start__ end____ width___ exp.time_
128 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000  -60.0000 178

#__ type_ start__ end____ width___ exp.time_
129 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000 -180.0000 178

#__ type_ start__ end____ width___ exp.time_
130 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000    0.0000 178

#__ type_ start__ end____ width___ exp.time_
131 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000   30.0000 178

#__ type_ start__ end____ width___ exp.time_
132 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000   60.0000 178

#__ type_ start__ end____ width___ exp.time_
133 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000   90.0000 178

#__ type_ start__ end____ width___ exp.time_
134 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000  120.0000 178

#__ type_ start__ end____ width___ exp.time_
135 omega  -48.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.0372    0.0000  -30.0000 178

#__ type_ start__ end____ width___ exp.time_
136 omega -156.00  -43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  -77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
137 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -120.0000 112
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0862850000
_diffrn_orient_matrix_UB_12      0.0804229000
_diffrn_orient_matrix_UB_13      -0.0942409000
_diffrn_orient_matrix_UB_21      0.1562253000
_diffrn_orient_matrix_UB_22      0.0608464000
_diffrn_orient_matrix_UB_23      -0.0551985000
_diffrn_orient_matrix_UB_31      0.0719376000
_diffrn_orient_matrix_UB_32      -0.0969835000
_diffrn_orient_matrix_UB_33      -0.0673669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3981
_reflns_number_total             4047
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0285P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0721
_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. 

 Comments on remaining CHECKCIF errors:
 Hirshfield test violations for atoms C2-C5, C8-C11 and N4 are caused by
 out-of-plane bending vibrations of cyano groups.
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.42315(9) 0.89973(7) 0.18574(6) 0.02575(18) Uani 1 1 d . . .
F2 F 0.68087(9) 0.90079(7) 0.10196(6) 0.02746(19) Uani 1 1 d . . .
F3 F 0.50854(11) 0.87223(7) 0.01907(6) 0.02884(19) Uani 1 1 d . . .
F4 F 0.64896(10) -0.05836(7) 0.63479(7) 0.0330(2) Uani 1 1 d . . .
F5 F 0.48819(10) -0.18469(7) 0.65073(7) 0.0304(2) Uani 1 1 d . . .
F6 F 0.47905(10) -0.11600(7) 0.78996(6) 0.0302(2) Uani 1 1 d . . .
N1 N 0.54819(13) 0.66286(9) 0.27512(8) 0.0184(2) Uani 1 1 d . . .
N2 N 0.65447(14) 0.63753(10) 0.09800(9) 0.0216(2) Uani 1 1 d . . .
N3 N 0.77871(18) 0.32851(11) 0.10742(10) 0.0350(3) Uani 1 1 d . . .
N4 N 0.58428(13) 0.36848(9) 0.45798(9) 0.0206(2) Uani 1 1 d . . .
N5 N 0.38941(13) 0.13512(9) 0.61377(8) 0.0188(2) Uani 1 1 d . . .
N6 N 0.21376(13) 0.00016(10) 0.64178(9) 0.0210(2) Uani 1 1 d . . .
N7 N -0.17683(14) 0.16840(10) 0.59712(9) 0.0226(2) Uani 1 1 d . . .
N8 N 0.17258(14) 0.43108(10) 0.52894(10) 0.0266(3) Uani 1 1 d . . .
N9 N 0.13556(14) 0.38767(10) 0.24351(9) 0.0236(2) Uani 1 1 d . . .
N10 N 0.08862(14) 0.22548(10) 0.21704(9) 0.0216(2) Uani 1 1 d . . .
C1 C 0.58467(15) 0.71241(11) 0.16497(10) 0.0192(3) Uani 1 1 d . . .
C2 C 0.66474(16) 0.52710(11) 0.17197(10) 0.0203(3) Uani 1 1 d . . .
C3 C 0.60076(15) 0.54198(11) 0.27969(10) 0.0185(3) Uani 1 1 d . . .
C4 C 0.72888(18) 0.41650(13) 0.13656(11) 0.0252(3) Uani 1 1 d . . .
C5 C 0.58937(15) 0.44784(11) 0.38034(10) 0.0184(3) Uani 1 1 d . . .
C6 C 0.54936(16) 0.84641(12) 0.11784(10) 0.0210(3) Uani 1 1 d . . .
C7 C 0.36394(16) 0.01919(11) 0.64220(10) 0.0192(3) Uani 1 1 d . . .
C8 C 0.13306(16) 0.11551(12) 0.60927(10) 0.0197(3) Uani 1 1 d . . .
C9 C 0.23926(16) 0.19774(11) 0.59203(10) 0.0189(3) Uani 1 1 d . . .
C10 C -0.03833(17) 0.14283(11) 0.60126(10) 0.0204(3) Uani 1 1 d . . .
C11 C 0.20441(15) 0.32717(12) 0.55685(11) 0.0205(3) Uani 1 1 d . . .
C12 C 0.49497(16) -0.08500(12) 0.67916(11) 0.0218(3) Uani 1 1 d . . .
C13 C 0.17804(16) 0.31470(12) 0.17481(11) 0.0236(3) Uani 1 1 d . . .
H13 H 0.2591 0.3248 0.1067 0.028 Uiso 1 1 calc R . .
C14 C -0.01608(16) 0.24208(12) 0.31589(11) 0.0226(3) Uani 1 1 d . . .
H14 H -0.0940 0.1916 0.3633 0.027 Uiso 1 1 calc R . .
C15 C 0.01298(16) 0.34375(12) 0.33272(11) 0.0233(3) Uani 1 1 d . . .
H15 H -0.0406 0.3784 0.3942 0.028 Uiso 1 1 calc R . .
C16 C 0.10007(18) 0.12542(12) 0.16678(11) 0.0269(3) Uani 1 1 d . . .
H16A H 0.1590 0.1457 0.0886 0.040 Uiso 1 1 calc R . .
H16B H -0.0125 0.1122 0.1711 0.040 Uiso 1 1 calc R . .
H16C H 0.1614 0.0513 0.2070 0.040 Uiso 1 1 calc R . .
C17 C 0.20345(18) 0.49933(13) 0.22447(12) 0.0290(3) Uani 1 1 d . . .
H17A H 0.3137 0.4943 0.1722 0.035 Uiso 1 1 calc R . .
H17B H 0.2207 0.5051 0.2959 0.035 Uiso 1 1 calc R . .
C18 C 0.09033(17) 0.61359(12) 0.17728(11) 0.0244(3) Uani 1 1 d . . .
H18A H -0.0155 0.6248 0.2327 0.029 Uiso 1 1 calc R . .
H18B H 0.0636 0.6057 0.1095 0.029 Uiso 1 1 calc R . .
C19 C 0.17767(18) 0.72301(12) 0.14874(12) 0.0262(3) Uani 1 1 d . . .
H19A H 0.2065 0.7284 0.2168 0.031 Uiso 1 1 calc R . .
H19B H 0.2833 0.7104 0.0935 0.031 Uiso 1 1 calc R . .
C20 C 0.07344(19) 0.84240(13) 0.10214(12) 0.0305(3) Uani 1 1 d . . .
H20A H 0.0422 0.8374 0.0356 0.046 Uiso 1 1 calc R . .
H20B H 0.1386 0.9082 0.0823 0.046 Uiso 1 1 calc R . .
H20C H -0.0277 0.8586 0.1584 0.046 Uiso 1 1 calc R . .
Li1 Li 0.5702(3) 0.23517(19) 0.60449(18) 0.0211(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
F1 C6 1.3398(15) . ?
F2 C6 1.3405(15) . ?
F3 C6 1.3359(15) . ?
F4 C12 1.3378(15) . ?
F5 C12 1.3339(15) . ?
F6 C12 1.3404(15) . ?
N1 C1 1.3434(16) . ?
N1 C3 1.3670(16) . ?
N1 Li1 2.123(2) 2_666 ?
N2 C1 1.3348(17) . ?
N2 C2 1.3604(17) . ?
N3 C4 1.1459(19) . ?
N4 C5 1.1454(17) . ?
N4 Li1 2.058(2) . ?
N5 C7 1.3461(16) . ?
N5 C9 1.3635(16) . ?
N5 Li1 2.081(2) . ?
N6 C7 1.3353(17) . ?
N6 C8 1.3614(17) . ?
N7 C10 1.1479(17) . ?
N7 Li1 2.081(2) 1_455 ?
N8 C11 1.1487(17) . ?
N9 C13 1.3274(18) . ?
N9 C15 1.3817(17) . ?
N9 C17 1.4714(17) . ?
N10 C13 1.3253(18) . ?
N10 C14 1.3764(17) . ?
N10 C16 1.4643(17) . ?
C1 C6 1.4938(17) . ?
C2 C3 1.3911(18) . ?
C2 C4 1.4337(19) . ?
C3 C5 1.4293(17) . ?
C7 C12 1.5006(18) . ?
C8 C9 1.3904(18) . ?
C8 C10 1.4305(18) . ?
C9 C11 1.4288(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3510(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5198(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5227(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Li1 N1 2.123(2) 2_666 ?
Li1 N7 2.081(2) 1_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 101.76(10) . . ?
C1 N1 Li1 123.70(10) . 2_666 ?
C3 N1 Li1 134.49(10) . 2_666 ?
C1 N2 C2 102.02(10) . . ?
C5 N4 Li1 175.76(12) . . ?
C7 N5 C9 102.04(10) . . ?
C7 N5 Li1 140.16(10) . . ?
C9 N5 Li1 117.66(10) . . ?
C7 N6 C8 101.92(10) . . ?
C10 N7 Li1 170.59(12) . 1_455 ?
C13 N9 C15 108.60(11) . . ?
C13 N9 C17 125.23(12) . . ?
C15 N9 C17 126.13(12) . . ?
C13 N10 C14 108.86(11) . . ?
C13 N10 C16 125.47(11) . . ?
C14 N10 C16 125.67(11) . . ?
N1 C1 C6 121.77(11) . . ?
N2 C1 N1 117.66(11) . . ?
N2 C1 C6 120.57(11) . . ?
N2 C2 C3 109.50(11) . . ?
N2 C2 C4 121.95(11) . . ?
C3 C2 C4 128.53(12) . . ?
N1 C3 C2 109.06(11) . . ?
N1 C3 C5 124.40(11) . . ?
C2 C3 C5 126.54(12) . . ?
N3 C4 C2 179.14(15) . . ?
N4 C5 C3 176.69(13) . . ?
F1 C6 F2 106.70(10) . . ?
F1 C6 C1 111.33(10) . . ?
F2 C6 C1 112.65(10) . . ?
F3 C6 F1 107.88(10) . . ?
F3 C6 F2 106.72(10) . . ?
F3 C6 C1 111.28(10) . . ?
N5 C7 C12 121.75(11) . . ?
N6 C7 N5 117.42(11) . . ?
N6 C7 C12 120.74(11) . . ?
N6 C8 C9 109.71(11) . . ?
N6 C8 C10 122.98(11) . . ?
C9 C8 C10 127.23(12) . . ?
N5 C9 C8 108.90(11) . . ?
N5 C9 C11 123.33(11) . . ?
C8 C9 C11 127.77(12) . . ?
N7 C10 C8 177.19(14) . . ?
N8 C11 C9 178.42(13) . . ?
F4 C12 F6 106.55(10) . . ?
F4 C12 C7 111.69(10) . . ?
F5 C12 F4 107.45(11) . . ?
F5 C12 F6 106.40(10) . . ?
F5 C12 C7 112.07(11) . . ?
F6 C12 C7 112.32(11) . . ?
N9 C13 H13 125.7 . . ?
N10 C13 N9 108.65(11) . . ?
N10 C13 H13 125.7 . . ?
N10 C14 H14 126.5 . . ?
C15 C14 N10 107.00(12) . . ?
C15 C14 H14 126.5 . . ?
N9 C15 H15 126.6 . . ?
C14 C15 N9 106.89(12) . . ?
C14 C15 H15 126.6 . . ?
N10 C16 H16A 109.5 . . ?
N10 C16 H16B 109.5 . . ?
N10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N9 C17 H17A 109.0 . . ?
N9 C17 H17B 109.0 . . ?
N9 C17 C18 113.03(11) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C17 C18 C19 109.58(11) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.63(12) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 Li1 N1 101.94(10) . 2_666 ?
N4 Li1 N5 108.06(10) . . ?
N4 Li1 N7 99.90(10) . 1_655 ?
N5 Li1 N1 102.85(10) . 2_666 ?
N7 Li1 N1 115.68(11) 1_655 2_666 ?
N7 Li1 N5 125.79(11) 1_655 . ?

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
C13 H13 N2 0.95 2.47 3.3417(17) 152.8 2_665
C16 H16C F1 0.98 2.50 3.3316(16) 142.9 1_545

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
N1 C1 C6 F1 -26.21(16) . . . . ?
N1 C1 C6 F2 93.61(14) . . . . ?
N1 C1 C6 F3 -146.59(12) . . . . ?
N2 C1 C6 F1 153.89(11) . . . . ?
N2 C1 C6 F2 -86.29(14) . . . . ?
N2 C1 C6 F3 33.51(16) . . . . ?
N2 C2 C3 N1 0.25(14) . . . . ?
N2 C2 C3 C5 179.94(12) . . . . ?
N5 C7 C12 F4 -27.95(16) . . . . ?
N5 C7 C12 F5 -148.58(11) . . . . ?
N5 C7 C12 F6 91.70(14) . . . . ?
N6 C7 C12 F4 155.48(11) . . . . ?
N6 C7 C12 F5 34.85(16) . . . . ?
N6 C7 C12 F6 -84.88(14) . . . . ?
N6 C8 C9 N5 -0.12(14) . . . . ?
N6 C8 C9 C11 179.56(12) . . . . ?
N9 C17 C18 C19 -174.06(11) . . . . ?
N10 C14 C15 N9 -0.03(14) . . . . ?
C1 N1 C3 C2 -0.19(13) . . . . ?
C1 N1 C3 C5 -179.88(12) . . . . ?
C1 N2 C2 C3 -0.20(14) . . . . ?
C1 N2 C2 C4 178.07(12) . . . . ?
C2 N2 C1 N1 0.08(15) . . . . ?
C2 N2 C1 C6 179.99(11) . . . . ?
C3 N1 C1 N2 0.07(15) . . . . ?
C3 N1 C1 C6 -179.84(11) . . . . ?
C4 C2 C3 N1 -177.87(13) . . . . ?
C4 C2 C3 C5 1.8(2) . . . . ?
C7 N5 C9 C8 0.26(13) . . . . ?
C7 N5 C9 C11 -179.43(12) . . . . ?
C7 N5 Li1 N1 -115.25(15) . . . 2_666 ?
C7 N5 Li1 N4 137.45(14) . . . . ?
C7 N5 Li1 N7 20.2(2) . . . 1_655 ?
C7 N6 C8 C9 -0.08(13) . . . . ?
C7 N6 C8 C10 -177.04(12) . . . . ?
C8 N6 C7 N5 0.28(14) . . . . ?
C8 N6 C7 C12 177.00(11) . . . . ?
C9 N5 C7 N6 -0.35(14) . . . . ?
C9 N5 C7 C12 -177.04(11) . . . . ?
C9 N5 Li1 N1 59.51(13) . . . 2_666 ?
C9 N5 Li1 N4 -47.80(14) . . . . ?
C10 C8 C9 N5 176.68(12) . . . . ?
C10 C8 C9 C11 -3.6(2) . . . . ?
C13 N9 C15 C14 0.35(15) . . . . ?
C13 N9 C17 C18 98.16(16) . . . . ?
C13 N10 C14 C15 -0.29(15) . . . . ?
C14 N10 C13 N9 0.51(15) . . . . ?
C15 N9 C13 N10 -0.53(15) . . . . ?
C15 N9 C17 C18 -79.03(16) . . . . ?
C16 N10 C13 N9 -179.27(11) . . . . ?
C16 N10 C14 C15 179.49(12) . . . . ?
C17 N9 C13 N10 -178.14(12) . . . . ?
C17 N9 C15 C14 177.93(12) . . . . ?
C17 C18 C19 C20 -179.26(12) . . . . ?
Li1 N1 C1 N2 -177.91(11) 2_666 . . . ?
Li1 N1 C1 C6 2.19(18) 2_666 . . . ?
Li1 N1 C3 C2 177.45(12) 2_666 . . . ?
Li1 N1 C3 C5 -2.2(2) 2_666 . . . ?
Li1 N5 C7 N6 174.90(13) . . . . ?
Li1 N5 C7 C12 -1.8(2) . . . . ?
Li1 N5 C9 C8 -176.30(10) . . . . ?
Li1 N5 C9 C11 4.00(17) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 940808'
