#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/28/2202883.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202883
loop_
_publ_author_name
'Helen L. Aberdeen'
'Robert E. Allan'
'Jonathan D. Crane'
_publ_section_title
'[3,5-Bis(trifluoromethyl)phenyl]{(E)-2-[(E)-3,5-bis(trifluoromethyl)phenylimino]-1-methylpropylidene}amine'
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1896
_journal_page_last               o1897
_journal_paper_doi               10.1107/S160053680302508X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C20 H12 F12 N2'
_chemical_formula_moiety         'C20 H12 F12 N2'
_chemical_formula_sum            'C20 H12 F12 N2'
_chemical_formula_weight         508.32
_chemical_name_systematic
;
[3,5-Bis(trifluoromethyl)phenyl]{(E)-2-[(E)-3,5-
bis(trifluoromethyl)phenylimino]-1-methylpropylidene}amine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                82.044(12)
_cell_angle_beta                 71.590(11)
_cell_angle_gamma                68.264(11)
_cell_formula_units_Z            1
_cell_length_a                   8.1406(12)
_cell_length_b                   8.2225(12)
_cell_length_c                   8.7087(13)
_cell_measurement_reflns_used    8717
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.31
_cell_measurement_theta_min      2.47
_cell_volume                     513.62(14)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2001)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  WinGX
_computing_structure_refinement
'WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10945
_diffrn_reflns_theta_full        32.31
_diffrn_reflns_theta_max         32.31
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.448
_refine_ls_extinction_coef       0.065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0590
_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)+(0.1038P)²+0.0549P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.1921
_reflns_number_gt                2477
_reflns_number_total             3638
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn6003.cif
_cod_data_source_block           I
_cod_original_cell_volume        513.62(13)
_cod_database_code               2202883
_cod_database_fobs_code          2202883
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_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_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_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_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) ?
