#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010477.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2010477
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1995
_journal_volume 51
_journal_page_first  291
_journal_page_last  293
_publ_section_title
;
Benzophenone O-4-(2,3,5,6-Tetrafluoro)pyridyloxime, Formed by
4-Substitution of Pentafluoropyridine by Benzophenone Oximate
;
loop_
_publ_author_name
  'Banks, R.E.'
  'Jondi, W.J.'
  'Pritchard, R.G.'
  'Tipping, A.E.'
_chemical_formula_moiety  ' C18 H10 F4 N2 O1 '
_chemical_formula_sum            'C18 H10 F4 N2 O'
_[local]_cod_chemical_formula_sum_orig 'C18 H10 F4 N2 O1'
_chemical_formula_structural  ' C18 H10 F4 N2 O1 '
_chemical_formula_weight  346.28
_chemical_melting_point  '325-327 K'
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  -x,-y,-z
_cell_length_a  5.603(2)
_cell_length_b  23.641(4)
_cell_length_c  12.643(2)
_cell_angle_alpha  73.420(10)
_cell_angle_beta  76.34(3)
_cell_angle_gamma  84.92(2)
_cell_volume  1559.0(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  286
_exptl_crystal_density_diffrn  1.475
_diffrn_ambient_temperature  296
_refine_ls_R_factor_obs  0.037
_refine_ls_wR_factor_obs  0.025
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
  F2 0.2899(3) 0.19669(8) 1.0084(2) 0.087(2)
  F3 0.2833(4) 0.25008(8) 0.7912(2) 0.104(2)
  F5 1.0279(4) 0.17466(9) 0.6702(2) 0.110(2)
  F6 1.0826(3) 0.12219(8) 0.8769(2) 0.088(2)
  O7 0.6769(4) 0.13532(9) 1.0662(2) 0.069(2)
  N4 0.6561(7) 0.21230(10)
  0.7301(3) 0.080(3)
  N8 0.8423(4) 0.08500(10)
  1.0892(2) 0.065(2)
  C1 0.6846(6) 0.15690(10)
  0.9535(3) 0.058(3)
  C2 0.4821(6) 0.19060(10)
  0.9259(3) 0.063(3)
  C3 0.4812(7) 0.2171(2) 0.8152(4) 0.074(3)
  C5 0.8440(7) 0.1800(2) 0.7567(3) 0.076(3)
  C6 0.8729(6) 0.15200(10)
  0.8639(3) 0.064(3)
  C9 0.8735(5) 0.07590(10)
  1.1898(3) 0.052(2)
  C10 0.7611(6) 0.11020(10)
  1.2716(2) 0.050(3)
  C11 0.5241(7) 0.1002(2) 1.3363(3) 0.073(3)
  C12 0.4335(8) 0.1307(2) 1.4161(3) 0.082(4)
  C13 0.5729(10) 0.1703(2) 1.4322(3) 0.078(4)
  C14 0.8056(9) 0.1802(2) 1.3688(3) 0.075(4)
  C15 0.9004(7) 0.1498(2) 1.2893(3) 0.060(3)
  C16 1.0497(6) 0.02690(10)
  1.2235(3) 0.056(3)
  C17 1.2468(7) 0.0140(2) 1.1452(3) 0.082(3)
  C18 1.4168(8) -0.0295(2) 1.1788(4) 0.090(4)
  C19 1.3894(8) -0.0601(2) 1.2897(4) 0.079(4)
  C20 1.1950(7) -0.0480(2) 1.3687(4) 0.079(3)
  C21 1.0264(7) -0.0039(2) 1.3351(3) 0.070(3)
  H11 0.430(5) 0.0730(10)
  1.320(2) 0.080(10)
  H12 0.276(6) 0.1210(10)
  1.462(3) 0.12(2)
  H13 0.512(5) 0.1910(10)
  1.489(3) 0.090(10)
  H14 0.912(5) 0.2070(10)
  1.378(2) 0.055(10)
  H15 1.061(5) 0.1570(10)
  1.245(2) 0.060(10)
  H17 1.267(5) 0.0360(10)
  1.069(3) 0.090(10)
  H18 1.565(6) -0.0360(10)
  1.121(3) 0.110(10)
  H19 1.505(5) -0.0880(10)
  1.313(2) 0.070(10)
  H20 1.165(5) -0.0720(10)
  1.451(3) 0.110(10)
  H21 0.891(5) 0.0040(10)
  1.390(2) 0.059(9)
  F32 0.3508(3) 0.42862(9) 0.4752(2) 0.094(2)
  F33 0.4843(4) 0.37205(9) 0.3132(2) 0.112(2)
  F35 1.1203(4) 0.28096(8) 0.4574(2) 0.097(2)
  F36 1.0195(3) 0.33188(7) 0.6262(2) 0.078(2)
  O37 0.5954(4) 0.40995(9) 0.6401(2) 0.068(2)
  N34 0.8009(7) 0.32670(10)
  0.3856(2) 0.076(3)
  N38 0.6031(4) 0.36876(10) 0.7495(2) 0.060(2)
  C31 0.6736(5) 0.38110(10)
  0.5591(3) 0.053(2)
  C32 0.5460(6) 0.3913(2) 0.4750(3) 0.063(3)
  C33 0.6156(8) 0.3632(2) 0.3932(3) 0.075(3)
  C35 0.9252(7) 0.31760(10)
  0.4643(3) 0.067(3)
  C36 0.8748(6) 0.34330(10)
  0.5523(3) 0.057(3)
  C39 0.4699(5) 0.38850(10)
  0.8291(2) 0.049(2)
  C40 0.3078(5) 0.44200(10)
  0.8157(2) 0.049(2)
  C41 0.1326(6) 0.4503(2) 0.7518(3) 0.065(3)
  C42 -0.0251(7) 0.4993(2) 0.7449(3) 0.079(3)
  C43 -0.0032(8) 0.5393(2) 0.8013(4) 0.085(4)
  C44 0.1699(8) 0.5323(2) 0.8634(4) 0.079(3)
  C45 0.3253(6) 0.4831(2) 0.8720(3) 0.060(3)
  C46 0.4798(5) 0.35100(10)
  0.9435(2) 0.049(2)
  C47 0.6893(7) 0.3173(2) 0.9641(3) 0.065(3)
  C48 0.6936(8) 0.2813(2) 1.0700(3) 0.076(3)
  C49 0.4898(9) 0.2776(2) 1.1563(3) 0.079(4)
  C50 0.2832(8) 0.3103(2) 1.1379(3) 0.072(3)
  C51 0.2778(6) 0.34720(10)
  1.0323(3) 0.060(3)
  H41 0.116(4) 0.4220(10)
  0.716(2) 0.049(9)
  H42 -0.142(5) 0.5000(10)
  0.697(2) 0.090(10)
  H43 -0.108(5) 0.5740(10)
  0.794(2) 0.090(10)
  H44 0.200(6) 0.560(2) 0.903(3) 0.110(10)
  H45 0.454(5) 0.4780(10)
  0.912(2) 0.059(10)
  H47 0.830(5) 0.3210(10)
  0.903(2) 0.064(10)
  H48 0.843(5) 0.2580(10)
  1.081(2) 0.100(10)
  H49 0.490(5) 0.2540(10)
  1.232(2) 0.090(10)
  H50 0.137(5) 0.3070(10)
  1.197(2) 0.080(10)
  H51 0.133(4) 0.3700(10)
  1.018(2) 0.053(9)
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
  F2 0.0750(10)
  0.094(2) 0.090(2) 0.0190(10)
  -0.0240(10)
  -0.0230(10)
  F3 0.099(2) 0.091(2) 0.123(2) 0.0120(10)
  -0.0670(10)
  0.0000(10)
  F5 0.115(2) 0.124(2) 0.0720(10)
  -0.0100(10)
  0.0020(10)
  -0.0140(10)
  F6 0.0700(10)
  0.096(2) 0.0880(10)
  0.0150(10)
  -0.0190(10)
  -0.0140(10)
  O7 0.083(2) 0.070(2) 0.058(2) 0.0220(10)
  -0.0320(10)
  -0.0160(10)
  N4 0.091(3) 0.076(2) 0.071(2) -0.010(2) -0.034(2) -0.001(2)
  N8 0.079(2) 0.056(2) 0.065(2) 0.0140(10)
  -0.031(2) -0.014(2)
  C1 0.066(2) 0.053(2) 0.061(2) 0.000(2) -0.031(2) -0.012(2)
  C2 0.063(3) 0.061(2) 0.065(3) 0.000(2) -0.022(2) -0.013(2)
  C3 0.073(3) 0.065(3) 0.089(3) -0.001(2) -0.046(3) -0.004(2)
  C5 0.081(3) 0.077(3) 0.065(3) -0.014(2) -0.011(2) -0.013(2)
  C6 0.062(3) 0.063(3) 0.067(3) 0.003(2) -0.022(2) -0.011(2)
  C9 0.056(2) 0.047(2) 0.054(2) -0.004(2) -0.019(2) -0.009(2)
  C10 0.051(2) 0.050(2) 0.047(2) 0.003(2) -0.019(2) -0.006(2)
  C11 0.061(3) 0.086(3) 0.074(3) -0.002(2) -0.020(2) -0.022(2)
  C12 0.061(3) 0.103(4) 0.069(3) 0.015(3) -0.012(3) -0.012(3)
  C13 0.099(4) 0.075(3) 0.056(3) 0.039(3) -0.026(3) -0.016(2)
  C14 0.094(4) 0.056(3) 0.083(3) 0.004(3) -0.033(3) -0.020(2)
  C15 0.061(3) 0.054(3) 0.065(3) 0.005(2) -0.015(2) -0.015(2)
  C16 0.065(2) 0.048(2) 0.055(2) 0.005(2) -0.020(2) -0.010(2)
  C17 0.097(3) 0.083(3) 0.058(3) 0.027(2) -0.015(2) -0.016(2)
  C18 0.093(3) 0.089(3) 0.078(3) 0.035(3) -0.012(3) -0.024(3)
  C19 0.089(3) 0.061(3) 0.089(3) 0.024(2) -0.036(3) -0.018(2)
  C20 0.089(3) 0.062(3) 0.074(3) 0.017(2) -0.021(2) -0.003(2)
  C21 0.070(3) 0.064(3) 0.064(3) 0.014(2) -0.013(2) -0.006(2)
  F32 0.0800(10)
  0.116(2) 0.0710(10)
  0.0220(10)
  -0.0210(10)
  -0.0050(10)
  F33 0.135(2) 0.139(2) 0.0710(10)
  -0.0340(10)
  -0.0420(10)
  -0.0190(10)
  F35 0.108(2) 0.079(2) 0.090(2) 0.0210(10)
  0.0110(10)
  -0.0320(10)
  F36 0.0730(10)
  0.0880(10)
  0.0730(10)
  0.0220(10)
  -0.0220(10)
  -0.0260(10)
  O37 0.095(2) 0.061(2) 0.0390(10)
  0.0240(10)
  -0.0080(10)
  -0.0150(10)
  N34 0.100(3) 0.072(2) 0.053(2) -0.013(2) -0.003(2) -0.021(2)
  N38 0.080(2) 0.056(2) 0.038(2) 0.0150(10)
  -0.0120(10)
  -0.0100(10)
  C31 0.062(2) 0.055(2) 0.038(2) 0.001(2) -0.005(2) -0.009(2)
  C32 0.065(2) 0.072(3) 0.044(2) 0.002(2) -0.004(2) -0.009(2)
  C33 0.087(3) 0.087(3) 0.047(2) -0.027(2) -0.017(2) -0.004(2)
  C35 0.074(3) 0.051(2) 0.066(3) 0.005(2) 0.006(2) -0.017(2)
  C36 0.059(2) 0.059(2) 0.050(2) 0.005(2) -0.006(2) -0.018(2)
  C39 0.054(2) 0.048(2) 0.044(2) 0.003(2) -0.008(2) -0.016(2)
  C40 0.053(2) 0.046(2) 0.042(2) 0.004(2) -0.004(2) -0.012(2)
  C41 0.066(3) 0.067(3) 0.062(2) 0.006(2) -0.014(2) -0.019(2)
  C42 0.065(3) 0.082(3) 0.075(3) 0.017(2) -0.015(2) -0.005(2)
  C43 0.078(3) 0.061(3) 0.086(3) 0.025(3) 0.007(2) -0.002(3)
  C44 0.087(3) 0.059(3) 0.081(3) 0.010(2) 0.002(2) -0.023(2)
  C45 0.063(2) 0.055(3) 0.060(2) 0.006(2) -0.007(2) -0.018(2)
  C46 0.059(2) 0.047(2) 0.042(2) 0.008(2) -0.015(2) -0.015(2)
  C47 0.064(3) 0.068(3) 0.059(3) 0.006(2) -0.016(2) -0.011(2)
  C48 0.080(3) 0.070(3) 0.076(3) 0.014(2) -0.033(3) -0.010(2)
  C49 0.111(4) 0.071(3) 0.054(3) 0.006(3) -0.034(3) -0.004(2)
  C50 0.092(3) 0.070(3) 0.044(2) 0.003(2) -0.005(2) -0.014(2)
  C51 0.070(3) 0.059(2) 0.048(2) 0.013(2) -0.009(2) -0.016(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  F2 C2 . . 1.340(3) ?
  F3 C3 . . 1.342(4) ?
  F5 C5 . . 1.341(4) ?
  F6 C6 . . 1.335(3) ?
  O7 N8 . . 1.446(3) yes
  O7 C1 . . 1.361(3) yes
  N4 C3 . . 1.297(4) ?
  N4 C5 . . 1.297(4) ?
  N8 C9 . . 1.278(3) yes
  C1 C2 . . 1.383(4) ?
  C1 C6 . . 1.378(4) ?
  C2 C3 . . 1.362(4) ?
  C5 C6 . . 1.369(4) ?
  C9 C10 . . 1.486(4) yes
  C9 C16 . . 1.487(4) yes
  C10 C11 . . 1.386(4) ?
  C10 C15 . . 1.367(4) ?
  C11 C12 . . 1.381(5) ?
  C12 C13 . . 1.356(5) ?
  C13 C14 . . 1.361(5) ?
  C14 C15 . . 1.379(5) ?
  C16 C17 . . 1.374(4) ?
  C16 C21 . . 1.372(4) ?
  C17 C18 . . 1.383(5) ?
  C18 C19 . . 1.361(5) ?
  C19 C20 . . 1.364(5) ?
  C20 C21 . . 1.385(4) ?
  F32 C32 . . 1.343(3) ?
  F33 C33 . . 1.347(4) ?
  F35 C35 . . 1.336(3) ?
  F36 C36 . . 1.334(3) ?
  O37 N38 . . 1.454(3) yes
  O37 C31 . . 1.356(3) yes
  N34 C33 . . 1.294(4) ?
  N34 C35 . . 1.304(4) ?
  N38 C39 . . 1.281(3) yes
  C31 C32 . . 1.372(4) ?
  C31 C36 . . 1.378(4) ?
  C32 C33 . . 1.349(4) ?
  C35 C36 . . 1.375(4) ?
  C39 C40 . . 1.483(4) yes
  C39 C46 . . 1.476(4) yes
  C40 C41 . . 1.380(4) ?
  C40 C45 . . 1.379(4) ?
  C41 C42 . . 1.389(5) ?
  C42 C43 . . 1.366(5) ?
  C43 C44 . . 1.357(5) ?
  C44 C45 . . 1.385(4) ?
  C46 C47 . . 1.394(4) ?
  C46 C51 . . 1.382(4) ?
  C47 C48 . . 1.371(4) ?
  C48 C49 . . 1.370(5) ?
  C49 C50 . . 1.363(5) ?
  C50 C51 . . 1.376(4) ?
  C11 H11 . . 0.96(3) ?
  C12 H12 . . 0.94(3) ?
  C13 H13 . . 0.95(3) ?
  C14 H14 . . 0.95(2) ?
  C15 H15 . . 0.94(2) ?
  C17 H17 . . 0.94(3) ?
  C18 H18 . . 1.00(3) ?
  C19 H19 . . 0.92(3) ?
  C20 H20 . . 1.01(3) ?
  C21 H21 . . 0.94(2) ?
  C41 H41 . . 0.92(2) ?
  C42 H42 . . 0.98(3) ?
  C43 H43 . . 0.95(3) ?
  C44 H44 . . 0.98(3) ?
  C45 H45 . . 0.95(2) ?
  C47 H47 . . 0.96(2) ?
  C48 H48 . . 0.97(3) ?
  C49 H49 . . 0.97(3) ?
  C50 H50 . . 0.96(3) ?
  C51 H51 . . 0.96(2) ?
_cod_database_code 2010477