data_2009015
_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 H10 F N O'
_chemical_formula_weight  215.22
_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  12.8200(10)
_cell_length_b  5.7870(10)
_cell_length_c  14.817(2)
_cell_angle_alpha  90.00
_cell_angle_beta  107.93(2)
_cell_angle_gamma  90.00
_cell_volume  1045.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.367
_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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  F1  .46549(8)  .0288(2)  .33804(9)  .0785(5) Uani d . 1 . F
  N1  .03176(11)  -.0938(2)  .12897(10)  .0435(4) Uani d . 1 . N
  O1  -.10950(11)  -.3620(2)  .00906(10)  .0588(4) Uani d . 1 . O
  H1A  -.0424(19)  -.305(4)  .0494(17)  .100(8) Uiso d . 1 . H
  C5  -.18535(14)  -.1998(3)  .00963(12)  .0432(5) Uani d . 1 . C
  C4  -.29375(14)  -.2401(3)  -.04244(13)  .0513(5) Uani d . 1 . C
  H4  -.31305(14)  -.3774(3)  -.07610(13)  .062 Uiso calc R 1 . H
  C3  -.37282(15)  -.0782(4)  -.04453(13)  .0542(5) Uani d . 1 . C
  H3  -.44532(15)  -.1069(4)  -.07972(13)  .065 Uiso calc R 1 . H
  C2  -.34582(15)  .1276(4)  .00522(13)  .0534(5) Uani d . 1 . C
  H2  -.39965(15)  .2367(4)  .00354(13)  .064 Uiso calc R 1 . H
  C1  -.23855(14)  .1681(3)  .05697(12)  .0478(5) Uani d . 1 . C
  H1  -.22024(14)  .3063(3)  .09011(12)  .057 Uiso calc R 1 . H
  C6  -.15640(13)  .0069(3)  .06102(11)  .0401(4) Uani d . 1 . C
  C7  -.04485(14)  .0537(3)  .11751(12)  .0431(4) Uani d . 1 . C
  H7  -.02830(14)  .1972(3)  .14667(12)  .052 Uiso calc R 1 . H
  C8  .14141(13)  -.0511(3)  .18541(11)  .0396(4) Uani d . 1 . C
  C13  .21691(14)  -.2188(3)  .18315(12)  .0466(5) Uani d . 1 . C
  H13  .19387(14)  -.3507(3)  .14658(12)  .056 Uiso calc R 1 . H
  C12  .32642(15)  -.1939(4)  .23447(13)  .0540(5) Uani d . 1 . C
  H12  .37731(15)  -.3070(4)  .23282(13)  .065 Uiso calc R 1 . H
  C11  .35777(14)  .0014(3)  .28758(13)  .0502(5) Uani d . 1 . C
  C10  .2855(2)  .1705(3)  .29254(13)  .0523(5) Uani d . 1 . C
  H10  .3093(2)  .3008(3)  .32992(13)  .063 Uiso calc R 1 . H
  C9  .17666(15)  .1443(3)  .24117(12)  .0496(5) Uani d . 1 . C
  H9  .12639(15)  .2580(3)  .24374(12)  .059 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
  F1  .0433(7)  .0934(10)  .0856(9)  -.0078(7)  .0005(6)  -.0012(7)
  N1  .0424(8)  .0424(9)  .0451(8)  -.0019(7)  .0126(6)  -.0031(7)
  O1  .0497(8)  .0463(8)  .0765(9)  -.0005(7)  .0137(7)  -.0158(7)
  C5  .0437(10)  .0410(10)  .0468(10)  -.0010(8)  .0165(8)  .0016(8)
  C4  .0499(11)  .0510(11)  .0509(11)  -.0077(10)  .0125(9)  -.0035(9)
  C3  .0421(10)  .0673(14)  .0500(10)  -.0058(10)  .0096(8)  .0050(10)
  C2  .0486(11)  .0582(12)  .0552(11)  .0071(10)  .0188(9)  .0071(10)
  C1  .0511(11)  .0447(10)  .0483(10)  .0017(9)  .0163(9)  -.0002(9)
  C6  .0439(10)  .0393(9)  .0385(9)  -.0016(8)  .0146(8)  .0023(8)
  C7  .0489(11)  .0380(9)  .0428(9)  -.0033(9)  .0146(8)  -.0033(8)
  C8  .0416(10)  .0411(9)  .0374(9)  -.0029(8)  .0140(7)  .0007(8)
  C13  .0509(11)  .0416(10)  .0481(10)  -.0003(9)  .0163(9)  -.0032(8)
  C12  .0462(11)  .0573(12)  .0590(11)  .0089(10)  .0168(9)  .0022(10)
  C11  .0397(10)  .0612(12)  .0476(10)  -.0052(10)  .0100(8)  .0060(10)
  C10  .0536(11)  .0527(12)  .0469(10)  -.0093(10)  .0100(9)  -.0071(9)
  C9  .0481(11)  .0460(11)  .0536(11)  .0006(9)  .0143(9)  -.0075(9)
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 C11 . 1.362(2) ?
  N1 C7 . 1.273(2) ?
  N1 C8 . 1.419(2) ?
  O1 C5 . 1.353(2) ?
  C5 C4 . 1.386(2) ?
  C5 C6 . 1.405(2) ?
  C4 C3 . 1.374(3) ?
  C3 C2 . 1.387(3) ?
  C2 C1 . 1.373(2) ?
  C1 C6 . 1.394(2) ?
  C6 C7 . 1.443(2) ?
  C8 C13 . 1.378(2) ?
  C8 C9 . 1.392(2) ?
  C13 C12 . 1.383(2) ?
  C12 C11 . 1.365(3) ?
  C11 C10 . 1.365(3) ?
  C10 C9 . 1.376(2) ?