##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-10-17
_journal_date_accepted     2003-10-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     12
_journal_page_first     o1896
_journal_page_last     o1897
_journal_paper_category     EO
_publ_contact_author_name     'Dr Jonathan D Crane'
_publ_contact_author_address
;
 Department of Chemistry
 University of Hull
 Cottingham Road
 Kingston-upon-Hull
 HU6 7RX
 UK
;
_publ_contact_author_email     j.d.crane@hull.ac.uk
_publ_contact_author_fax     '+44 1482 466410'
_publ_contact_author_phone     '+44 1482 465457'
_publ_section_title
;
[3,5-Bis(trifluoromethyl)phenyl]{(E)-2-[(E)-3,5-
bis(trifluoromethyl)phenylimino]-1-methylpropylidene}amine
;
loop_
    _publ_author_name
    _publ_author_address
    'Helen L. Aberdeen'
;
Department of Chemistry
University of Hull
Cottingham Road
Kingston-upon-Hull HU6 7RX
England
;
    'Robert E. Allan'
;
BP Chemicals Ltd.
Hull Research & Technology Centre
Saltend
Kingston-upon-Hull HU12 8DS
England
;
    'Jonathan D. Crane'
;
Department of Chemistry
University of Hull
Cottingham Road
Kingston-upon-Hull HU6 7RX
England
;
data_I
_chemical_name_systematic
;
[3,5-Bis(trifluoromethyl)phenyl]{(E)-2-[(E)-3,5-
bis(trifluoromethyl)phenylimino]-1-methylpropylidene}amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H12 F12 N2'
_chemical_formula_sum     'C20 H12 F12 N2'
_chemical_formula_iupac     'C20 H12 F12 N2'
_chemical_formula_weight     508.32
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.1406(12)
_cell_length_b     8.2225(12)
_cell_length_c     8.7087(13)
_cell_angle_alpha     82.044(12)
_cell_angle_beta     71.590(11)
_cell_angle_gamma     68.264(11)
_cell_volume     513.62(13)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     8717
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     32.31
_cell_measurement_temperature     150(2)
_exptl_crystal_description     lath
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.643
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     254
_exptl_absorpt_coefficient_mu     0.174
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 The crystal was mounted under the perfluoro-polyether
 PFO-XR75 (Lancaster Synthesis).
 A total of 290 frames (1 minute exposure) were collected
 (phi/omega: 10/175-180, 55/25-165, 160/25-170,
 delta-omega = 1 deg.)
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS-II'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10945
_diffrn_reflns_av_R_equivalents     0.0357
_diffrn_reflns_av_sigmaI/netI     0.0339
_diffrn_reflns_theta_min     2.47
_diffrn_reflns_theta_max     32.31
_diffrn_reflns_theta_full     32.31
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     3638
_reflns_number_gt     2477
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0793
_refine_ls_R_factor_gt     0.0590
_refine_ls_wR_factor_gt     0.1824
_refine_ls_wR_factor_ref     0.1921
_refine_ls_goodness_of_fit_ref     1.147
_refine_ls_restrained_S_all     1.147
_refine_ls_number_reflns     3638
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.1038P)²+0.0549P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.619
_refine_diff_density_min     -0.448
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.065(17)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    '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'
    '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2001)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED (Stoe & Cie, 2001)'
_computing_structure_solution
                    'X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement
                         'WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    F1 0.8750(2) 0.7737(2) 0.0966(2) 0.0691(4) Uani d . 1 . . F
    F2 0.8530(2) 0.7511(3) 0.3476(2) 0.0840(6) Uani d . 1 . . F
    F3 1.00766(17) 0.5284(2) 0.1932(2) 0.0699(5) Uani d . 1 . . F
    F4 0.4303(3) 0.2896(2) 0.0917(3) 0.0693(6) Uani d P 0.887(2) A 1 F
    F5 0.4953(5) 0.1598(2) 0.2999(2) 0.0918(9) Uani d P 0.887(2) A 1 F
    F6 0.7091(3) 0.1735(3) 0.0907(4) 0.0996(10) Uani d P 0.887(2) A 1 F
    F7 0.641(3) 0.1373(17) 0.228(3) 0.0693(6) Uani d P 0.113(2) A 2 F
    F8 0.614(5) 0.249(2) 0.0361(17) 0.0918(9) Uani d P 0.113(2) A 2 F
    F9 0.377(2) 0.244(3) 0.239(3) 0.0996(10) Uani d P 0.113(2) A 2 F
    N1 0.18628(17) 0.80521(17) 0.48625(15) 0.0303(3) Uani d . 1 . . N
    C1 0.08685(19) 0.95044(18) 0.43766(17) 0.0267(3) Uani d . 1 . . C
    C2 0.1239(2) 1.0281(2) 0.2698(2) 0.0391(4) Uani d . 1 . . C
    H2C 0.2426 0.9531 0.2021 0.047 Uiso calc R 1 . . H
    H2B 0.1282 1.1450 0.2734 0.047 Uiso calc R 1 . . H
    H2A 0.0253 1.0370 0.2239 0.047 Uiso calc R 1 . . H
    C3 0.35389(19) 0.69984(18) 0.38339(17) 0.0272(3) Uani d . 1 . . C
    C4 0.5147(2) 0.73974(18) 0.34964(18) 0.0296(3) Uani d . 1 . . C
    H4 0.5094 0.8455 0.3866 0.036 Uiso calc R 1 . . H
    C5 0.6824(2) 0.6240(2) 0.26176(18) 0.0299(3) Uani d . 1 . . C
    C6 0.6941(2) 0.46924(19) 0.20517(17) 0.0298(3) Uani d . 1 . . C
    H6 0.8092 0.3907 0.1453 0.036 Uiso calc R 1 . . H
    C7 0.5334(2) 0.43248(19) 0.23842(18) 0.0294(3) Uani d . 1 A . C
    C8 0.3644(2) 0.54413(19) 0.32800(18) 0.0295(3) Uani d . 1 . . C
    H8 0.2566 0.5146 0.3514 0.035 Uiso calc R 1 . . H
    C9 0.8534(2) 0.6686(3) 0.2271(2) 0.0417(4) Uani d . 1 . . C
    C10 0.5418(3) 0.2648(2) 0.1809(2) 0.0386(4) Uani d . 1 . . C
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    F1 0.0545(8) 0.0723(9) 0.0774(10) -0.0373(7) -0.0046(7) 0.0178(7)
    F2 0.0597(9) 0.1383(16) 0.0763(10) -0.0627(10) 0.0009(7) -0.0421(10)
    F3 0.0281(6) 0.0583(8) 0.1160(13) -0.0096(5) -0.0165(7) -0.0042(8)
    F4 0.1058(14) 0.0449(8) 0.0876(12) -0.0263(8) -0.0693(11) 0.0009(7)
    F5 0.205(3) 0.0450(9) 0.0498(9) -0.0684(14) -0.0447(13) 0.0113(7)
    F6 0.0545(11) 0.0784(13) 0.155(3) -0.0102(9) 0.0036(12) -0.0842(16)
    F7 0.1058(14) 0.0449(8) 0.0876(12) -0.0263(8) -0.0693(11) 0.0009(7)
    F8 0.205(3) 0.0450(9) 0.0498(9) -0.0684(14) -0.0447(13) 0.0113(7)
    F9 0.0545(11) 0.0784(13) 0.155(3) -0.0102(9) 0.0036(12) -0.0842(16)
    N1 0.0252(6) 0.0275(6) 0.0303(6) -0.0022(4) -0.0053(4) -0.0024(4)
    C1 0.0229(6) 0.0248(6) 0.0299(6) -0.0055(5) -0.0066(5) -0.0032(5)
    C2 0.0319(8) 0.0354(8) 0.0321(7) 0.0013(6) -0.0022(6) 0.0021(6)
    C3 0.0252(6) 0.0241(6) 0.0266(6) -0.0031(5) -0.0067(5) -0.0001(5)
    C4 0.0293(7) 0.0246(6) 0.0319(7) -0.0064(5) -0.0079(5) -0.0017(5)
    C5 0.0253(6) 0.0306(6) 0.0304(6) -0.0078(5) -0.0066(5) 0.0016(5)
    C6 0.0249(6) 0.0282(6) 0.0286(6) -0.0025(5) -0.0046(5) -0.0026(5)
    C7 0.0302(7) 0.0257(6) 0.0292(6) -0.0050(5) -0.0092(5) -0.0024(5)
    C8 0.0264(6) 0.0278(6) 0.0322(7) -0.0065(5) -0.0085(5) -0.0019(5)
    C9 0.0290(8) 0.0429(9) 0.0498(10) -0.0129(7) -0.0048(7) -0.0043(7)
    C10 0.0427(9) 0.0310(7) 0.0409(8) -0.0074(6) -0.0142(7) -0.0078(6)
_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.
 Weighted least-squares planes through the starred atoms
 (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II-A),807).
 Plane  1
 Atom              d          s           d/s      (d/s)**2
 C1    *         0.0000     0.0016       0.000        0.000
 N1    *         0.0000     0.0015       0.000        0.000
 C2    *         0.0000     0.0020       0.000        0.000
 C3              0.0527     0.0016      32.357     1047.007
                                                ============
               Sum((d/s)**2) for starred atoms        0.000
 Plane  2
 Atom              d          s           d/s      (d/s)**2
 C3    *         0.0011     0.0014       0.796        0.634
 C4    *         0.0036     0.0015       2.397        5.748
 C5    *        -0.0033     0.0015      -2.174        4.725
 C6    *        -0.0021     0.0014      -1.427        2.037
 C7    *         0.0073     0.0015       4.852       23.542
 C8    *        -0.0067     0.0015      -4.460       19.887
 N1             -0.1344     0.0013    -105.129    11052.209
 C9             -0.0046     0.0020      -2.304        5.308
 C10            -0.0108     0.0018      -5.874       34.507
                                                ============
               Sum((d/s)**2) for starred atoms       56.573
 Chi-squared at 95% for  3 degrees of freedom:  7.81
 The group of atoms deviates significantly from planarity
 Plane  3
 Atom              d          s           d/s      (d/s)**2
 N1    *         0.0000     0.0013       0.000        0.000
 C4    *         0.0000     0.0015       0.000        0.000
 C8    *         0.0000     0.0015       0.000        0.000
 C3              0.0471     0.0014      32.873     1080.603
                                                ============
               Sum((d/s)**2) for starred atoms        0.000
 Dihedral angles formed by LSQ-planes
 Plane - plane            angle (s.u.)             angle (s.u.)
   1       2              77.25( 0.12)             102.75( 0.12)
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    F1 C9 . 1.336(2) ?
    F2 C9 . 1.324(3) ?
    F3 C9 . 1.335(2) ?
    F4 C10 . 1.316(2) ?
    F5 C10 . 1.307(3) ?
    F6 C10 . 1.329(2) ?
    F7 C10 . 1.176(13) ?
    F8 C10 . 1.214(16) ?
    F9 C10 . 1.345(16) ?
    N1 C1 . 1.2731(19) yes
    N1 C3 . 1.4079(18) yes
    C1 C2 . 1.497(2) yes
    C1 C1 2_576 1.505(3) yes
    C2 H2C . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2A . 0.9800 ?
    C3 C8 . 1.394(2) ?
    C3 C4 . 1.399(2) ?
    C4 C5 . 1.391(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.387(2) ?
    C5 C9 . 1.498(2) ?
    C6 C7 . 1.384(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.389(2) ?
    C7 C10 . 1.502(2) ?
    C8 H8 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C3 . . 121.92(13) yes
    N1 C1 C2 . . 126.47(13) yes
    N1 C1 C1 . 2_576 115.74(16) yes
    C2 C1 C1 . 2_576 117.77(15) yes
    C1 C2 H2C . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2C C2 H2B . . 109.5 ?
    C1 C2 H2A . . 109.5 ?
    H2C C2 H2A . . 109.5 ?
    H2B C2 H2A . . 109.5 ?
    C8 C3 C4 . . 119.29(13) ?
    C8 C3 N1 . . 119.56(13) yes
    C4 C3 N1 . . 120.81(13) yes
    C5 C4 C3 . . 119.74(13) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C6 C5 C4 . . 121.40(13) ?
    C6 C5 C9 . . 119.59(14) ?
    C4 C5 C9 . . 119.01(14) ?
    C7 C6 C5 . . 118.12(13) ?
    C7 C6 H6 . . 120.9 ?
    C5 C6 H6 . . 120.9 ?
    C6 C7 C8 . . 121.81(13) ?
    C6 C7 C10 . . 119.42(13) ?
    C8 C7 C10 . . 118.74(14) ?
    C7 C8 C3 . . 119.62(14) ?
    C7 C8 H8 . . 120.2 ?
    C3 C8 H8 . . 120.2 ?
    F2 C9 F3 . . 108.43(18) ?
    F2 C9 F1 . . 105.95(18) ?
    F3 C9 F1 . . 104.06(16) ?
    F2 C9 C5 . . 112.63(15) ?
    F3 C9 C5 . . 112.76(15) ?
    F1 C9 C5 . . 112.42(16) ?
    F7 C10 F8 . . 99.7(15) ?
    F7 C10 F5 . . 53.0(12) ?
    F8 C10 F5 . . 134.4(6) ?
    F7 C10 F4 . . 132.4(6) ?
    F8 C10 F4 . . 63.8(15) ?
    F5 C10 F4 . . 105.4(2) ?
    F7 C10 F6 . . 56.5(12) ?
    F8 C10 F6 . . 46.2(13) ?
    F5 C10 F6 . . 106.3(2) ?
    F4 C10 F6 . . 105.8(2) ?
    F7 C10 F9 . . 103.2(15) ?
    F8 C10 F9 . . 116.5(16) ?
    F5 C10 F9 . . 53.4(12) ?
    F4 C10 F9 . . 57.0(12) ?
    F6 C10 F9 . . 136.7(5) ?
    F7 C10 C7 . . 114.4(6) ?
    F8 C10 C7 . . 112.0(6) ?
    F5 C10 C7 . . 112.76(15) ?
    F4 C10 C7 . . 113.08(15) ?
    F6 C10 C7 . . 112.89(16) ?
    F9 C10 C7 . . 110.4(5) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 C1 C2 . . . . 2.5(2) yes
    C3 N1 C1 C1 . . . 2_576 -179.06(14) yes
    C1 N1 C3 C8 . . . . -107.89(17) yes
    C1 N1 C3 C4 . . . . 78.82(19) yes
    C8 C3 C4 C5 . . . . -0.1(2) ?
    N1 C3 C4 C5 . . . . 173.24(13) ?
    C3 C4 C5 C6 . . . . 0.5(2) ?
    C3 C4 C5 C9 . . . . -179.83(14) ?
    C4 C5 C6 C7 . . . . 0.0(2) ?
    C9 C5 C6 C7 . . . . -179.61(15) ?
    C5 C6 C7 C8 . . . . -1.1(2) ?
    C5 C6 C7 C10 . . . . -179.14(14) ?
    C6 C7 C8 C3 . . . . 1.5(2) ?
    C10 C7 C8 C3 . . . . 179.60(14) ?
    C4 C3 C8 C7 . . . . -0.9(2) ?
    N1 C3 C8 C7 . . . . -174.31(13) ?
    C6 C5 C9 F2 . . . . -144.78(18) ?
    C4 C5 C9 F2 . . . . 35.6(2) ?
    C6 C5 C9 F3 . . . . -21.7(2) ?
    C4 C5 C9 F3 . . . . 158.67(16) ?
    C6 C5 C9 F1 . . . . 95.61(19) ?
    C4 C5 C9 F1 . . . . -84.1(2) ?
    C6 C7 C10 F7 . . . . 57.6(14) ?
    C8 C7 C10 F7 . . . . -120.6(14) ?
    C6 C7 C10 F8 . . . . -54.9(16) ?
    C8 C7 C10 F8 . . . . 127.0(16) ?
    C6 C7 C10 F5 . . . . 115.8(2) ?
    C8 C7 C10 F5 . . . . -62.4(3) ?
    C6 C7 C10 F4 . . . . -124.7(2) ?
    C8 C7 C10 F4 . . . . 57.2(2) ?
    C6 C7 C10 F6 . . . . -4.7(3) ?
    C8 C7 C10 F6 . . . . 177.2(2) ?
    C6 C7 C10 F9 . . . . 173.5(14) ?
    C8 C7 C10 F9 . . . . -4.6(14) ?
