data_2011460
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e481
_journal_page_last  e482
_publ_section_title
;
(E)-N-Benzylidene-3-chloro-4-fluoroaniline
;
loop_
_publ_author_name
  'Arjuna Gowda, K. V.'
  'Kokila, M. K.'
  'Puttaraja'
  'Kulkarni, M. V.'
  'Shivaprakash, N. C.'
_chemical_name_common  'organofluorine derivative'
_chemical_formula_moiety  'C13 H9 Cl F N'
_chemical_formula_sum  'C13 H9 Cl F N'
_chemical_formula_structural  'C13 H9 Cl F N'
_chemical_formula_weight  233.66
_chemical_melting_point  (39+273)
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  5.7874(7)
_cell_length_b  7.5327(7)
_cell_length_c  25.3418(19)
_cell_angle_alpha  90.00
_cell_angle_beta  94.227(8)
_cell_angle_gamma  90.00
_cell_volume  1101.76(19)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.409
_exptl_crystal_density_meas  1.408
_diffrn_ambient_temperature  293(2)
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
  Cl  .23690(9)  .33499(8)  .007812(18)  .0752(2) Uani d . 1 . . Cl
  F  -.2126(2)  .16109(18)  -.01121(4)  .0768(4) Uani d . 1 . . F
  N  .0970(2)  .1474(2)  .20009(6)  .0526(4) Uani d . 1 . . N
  C1  .0272(3)  .1607(2)  .14549(6)  .0469(4) Uani d . 1 . . C
  C2  .1567(3)  .2408(2)  .10776(6)  .0508(4) Uani d . 1 . . C
  H2  .2980  .2940  .1180  .061 Uiso calc R 1 . . H
  C3  .0741(3)  .2409(2)  .05517(6)  .0522(4) Uani d . 1 . . C
  C4  -.1356(3)  .1627(2)  .04033(7)  .0556(5) Uani d . 1 . . C
  C5  -.2655(3)  .0829(3)  .07672(8)  .0594(5) Uani d . 1 . . C
  H5  -.4065  .0299  .0662  .071 Uiso calc R 1 . . H
  C6  -.1834(3)  .0825(2)  .12925(7)  .0531(4) Uani d . 1 . . C
  H6  -.2707  .0289  .1542  .064 Uiso calc R 1 . . H
  C7  .2863(3)  .2076(2)  .21913(7)  .0526(4) Uani d . 1 . . C
  H7  .3813  .2671  .1969  .063 Uiso calc R 1 . . H
  C1'  .3642(3)  .1879(2)  .27521(6)  .0464(4) Uani d . 1 . . C
  C2'  .2266(3)  .1038(2)  .31055(7)  .0530(4) Uani d . 1 . . C
  H2'  .0824  .0589  .2987  .064 Uiso calc R 1 . . H
  C3'  .3038(3)  .0869(3)  .36310(7)  .0603(5) Uani d . 1 . . C
  H3'  .2115  .0304  .3865  .072 Uiso calc R 1 . . H
  C4'  .5174(3)  .1535(2)  .38112(7)  .0578(5) Uani d . 1 . . C
  H4'  .5676  .1435  .4167  .069 Uiso calc R 1 . . H
  C5'  .6561(3)  .2345(3)  .34642(7)  .0590(5) Uani d . 1 . . C
  H5'  .8006  .2784  .3585  .071 Uiso calc R 1 . . H
  C6'  .5807(3)  .2506(3)  .29361(7)  .0564(4) Uani d . 1 . . C
  H6'  .6759  .3038  .2702  .068 Uiso calc R 1 . . H
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
  Cl  .0817(4)  .1006(5)  .0448(3)  .0019(3)  .0146(2)  .0118(2)
  F  .0834(8)  .1009(10)  .0433(6)  .0094(6)  -.0146(5)  -.0051(5)
  N  .0523(8)  .0650(9)  .0402(7)  -.0025(6)  .0026(6)  .0031(6)
  C1  .0507(9)  .0504(8)  .0396(8)  .0052(7)  .0023(7)  .0007(6)
  C2  .0494(9)  .0596(10)  .0431(8)  .0005(7)  .0020(7)  -.0010(7)
  C3  .0595(10)  .0588(10)  .0386(8)  .0101(8)  .0060(7)  .0012(7)
  C4  .0630(10)  .0615(10)  .0409(9)  .0133(8)  -.0067(7)  -.0048(7)
  C5  .0525(9)  .0659(11)  .0580(10)  .0001(8)  -.0087(8)  -.0030(9)
  C6  .0494(9)  .0591(10)  .0507(9)  .0001(7)  .0029(7)  .0028(8)
  C7  .0549(9)  .0621(10)  .0411(9)  -.0023(8)  .0056(7)  .0042(7)
  C1'  .0486(8)  .0508(9)  .0398(8)  .0019(6)  .0034(6)  -.0011(6)
  C2'  .0511(9)  .0648(10)  .0431(9)  -.0090(7)  .0039(7)  -.0024(7)
  C3'  .0686(11)  .0714(11)  .0416(9)  -.0126(9)  .0089(8)  .0019(8)
  C4'  .0694(11)  .0634(11)  .0393(8)  .0037(8)  -.0053(8)  -.0035(7)
  C5'  .0505(9)  .0670(11)  .0580(10)  -.0023(8)  -.0064(8)  -.0045(9)
  C6'  .0517(9)  .0655(11)  .0522(10)  -.0073(8)  .0053(7)  .0043(8)
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
  Cl C3 . 1.7310(18) ?
  F C4 . 1.349(2) ?
  N C7 . 1.249(2) ?
  N C1 . 1.416(2) ?
  C1 C6 . 1.388(2) ?
  C1 C2 . 1.395(2) ?
  C2 C3 . 1.382(2) ?
  C3 C4 . 1.377(3) ?
  C4 C5 . 1.370(3) ?
  C5 C6 . 1.380(2) ?
  C7 C1' . 1.466(2) ?
  C1' C6' . 1.387(2) ?
  C1' C2' . 1.394(2) ?
  C2' C3' . 1.379(2) ?
  C3' C4' . 1.380(3) ?
  C4' C5' . 1.376(3) ?
  C5' C6' . 1.382(2) ?