#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2009017.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_2009017
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1707
_journal_page_last  1710
_publ_section_title
;
Four N-(2-hydroxybenzylidene)aniline derivatives
;
loop_
_publ_author_name
  'Burgess, John'
  'Fawcett, John'
  'Russell, David R.'
  'Gilani, Syeda R.'
  'Palma, Vitor'
_chemical_formula_sum  'C13 H9 Cl2 N O'
_chemical_formula_weight  266.11
_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  27.419(7)
_cell_length_b  6.901(2)
_cell_length_c  6.1370(10)
_cell_angle_alpha  90.00
_cell_angle_beta  95.57(2)
_cell_angle_gamma  90.00
_cell_volume  1155.8(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  190(2)
_exptl_crystal_density_diffrn  1.529
_diffrn_ambient_temperature  190(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1  .45816(2)  -.07373(11)  .16871(12)  .0408(3) Uani d . 1 . Cl
  Cl2  .03806(2)  .04226(11)  -.27013(12)  .0458(3) Uani d . 1 . Cl
  O1  .28194(7)  .0709(3)  .6119(3)  .0324(5) Uani d . 1 . O
  H1A  .2582(11)  .042(4)  .523(5)  .047(10) Uiso d . 1 . H
  N1  .23046(7)  -.0255(3)  .2505(3)  .0226(5) Uani d . 1 . N
  C1  .36056(8)  -.0704(3)  .1896(4)  .0227(6) Uani d . 1 . C
  H1  .35737(8)  -.1192(3)  .0424(4)  .027 Uiso d R 1 . H
  C2  .40545(8)  -.0350(3)  .2995(4)  .0251(6) Uani d . 1 . C
  C3  .40968(9)  .0380(4)  .5116(4)  .0275(6) Uani d . 1 . C
  H3  .44151(9)  .0571(4)  .5885(4)  .033 Uiso d R 1 . H
  C4  .36804(9)  .0722(3)  .6131(4)  .0256(6) Uani d . 1 . C
  H4  .37114(9)  .1292(3)  .7564(4)  .031 Uiso d R 1 . H
  C5  .32198(9)  .0362(3)  .5055(4)  .0230(6) Uani d . 1 . C
  C6  .31779(8)  -.0343(3)  .2887(4)  .0213(5) Uani d . 1 . C
  C7  .27048(9)  -.0555(3)  .1643(4)  .0228(6) Uani d . 1 . C
  H7  .26982(9)  -.0866(3)  .0116(4)  .027 Uiso d R 1 . H
  C8  .18521(8)  -.0175(3)  .1177(4)  .0210(6) Uani d . 1 . C
  C9  .18145(9)  .0625(3)  -.0907(4)  .0238(6) Uani d . 1 . C
  H9  .21022(9)  .1077(3)  -.1525(4)  .029 Uiso d R 1 . H
  C10  .13617(9)  .0805(3)  -.2094(4)  .0256(6) Uani d . 1 . C
  H10  .13393(9)  .1330(3)  -.3549(4)  .031 Uiso d R 1 . H
  C11  .09481(9)  .0182(4)  -.1185(4)  .0260(6) Uani d . 1 . C
  C12  .09772(9)  -.0609(3)  .0888(4)  .0278(6) Uani d . 1 . C
  H12  .06852(9)  -.1015(3)  .1505(4)  .033 Uiso d R 1 . H
  C13  .14299(9)  -.0773(3)  .2067(4)  .0245(6) Uani d . 1 . C
  H13  .14519(9)  -.1322(3)  .3510(4)  .029 Uiso d 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
  Cl1  .0208(4)  .0567(5)  .0462(5)  -.0005(3)  .0100(3)  -.0046(3)
  Cl2  .0248(4)  .0612(5)  .0489(5)  .0036(3)  -.0090(3)  .0001(4)
  O1  .0259(10)  .0473(12)  .0247(10)  .0001(8)  .0061(8)  -.0066(9)
  N1  .0210(12)  .0244(11)  .0225(11)  -.0006(8)  .0030(9)  .0010(9)
  C1  .0280(14)  .0206(13)  .0197(12)  .0009(10)  .0038(11)  .0009(10)
  C2  .0196(13)  .0256(13)  .0305(14)  .0011(10)  .0047(10)  .0031(12)
  C3  .0226(14)  .0280(13)  .0305(15)  -.0014(10)  -.0048(11)  .0025(12)
  C4  .0290(14)  .0251(14)  .0219(13)  -.0020(10)  -.0020(11)  -.0021(11)
  C5  .0252(14)  .0213(12)  .0233(13)  .0017(10)  .0061(11)  .0015(11)
  C6  .0221(13)  .0202(12)  .0217(13)  -.0001(10)  .0030(10)  .0011(11)
  C7  .0254(14)  .0225(13)  .0210(13)  .0017(10)  .0041(11)  .0014(10)
  C8  .0212(13)  .0179(12)  .0241(13)  .0004(10)  .0039(10)  -.0025(11)
  C9  .0217(13)  .0243(13)  .0264(13)  -.0013(10)  .0071(10)  -.0019(11)
  C10  .0298(15)  .0265(14)  .0204(13)  .0018(10)  .0019(11)  -.0005(10)
  C11  .0213(14)  .0249(13)  .0312(14)  .0031(10)  -.0010(11)  -.0041(12)
  C12  .0212(14)  .0277(14)  .036(2)  -.0012(10)  .0082(11)  -.0005(12)
  C13  .0265(14)  .0249(13)  .0229(13)  -.0001(10)  .0063(11)  -.0012(10)
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
  Cl1 C2 . 1.741(2) ?
  Cl2 C11 . 1.742(2) ?
  O1 C5 . 1.352(3) ?
  N1 C7 . 1.281(3) ?
  N1 C8 . 1.418(3) ?
  C1 C2 . 1.367(3) ?
  C1 C6 . 1.395(3) ?
  C2 C3 . 1.390(4) ?
  C3 C4 . 1.373(4) ?
  C4 C5 . 1.390(3) ?
  C5 C6 . 1.411(3) ?
  C6 C7 . 1.447(3) ?
  C8 C13 . 1.390(3) ?
  C8 C9 . 1.388(3) ?
  C9 C10 . 1.383(3) ?
  C10 C11 . 1.380(4) ?
  C11 C12 . 1.380(4) ?
  C12 C13 . 1.379(3) ?