#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2300059.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_2300059
_journal_name_full  'Journal of Applied Crystallography'
_journal_year  2004
_journal_volume  37
_journal_page_first  288
_journal_page_last  294
_chemical_formula_sum  'C14 H11 Cl2 N O2'
_chemical_formula_weight  296.14
_symmetry_cell_setting  Monoclinic
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  20.2906(4)
_cell_length_b  6.99520(10)
_cell_length_c  20.1137(4)
_cell_angle_alpha  90.00
_cell_angle_beta  109.6630(10)
_cell_angle_gamma  90.00
_cell_volume  2688.40(8)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.463
_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
  C1 0.22591(8) 0.3689(2) 0.33540(9) 0.0390(4) Uani d . 1 . . C
  C2 0.23892(10) 0.4480(2) 0.27761(10) 0.0461(4) Uani d . 1 . . C
  C3 0.18921(11) 0.4454(3) 0.21117(10) 0.0522(5) Uani d . 1 . . C
  C4 0.12472(11) 0.3628(3) 0.20170(10) 0.0508(5) Uani d . 1 . . C
  C5 0.11032(10) 0.2842(3) 0.25842(9) 0.0442(4) Uani d . 1 . . C
  C6 0.16006(8) 0.2874(2) 0.32571(8) 0.0369(4) Uani d . 1 . . C
  C7 0.09028(8) 0.0932(2) 0.38114(8) 0.0380(4) Uani d . 1 . . C
  C8 0.08254(9) -0.0869(3) 0.34864(9) 0.0437(4) Uani d . 1 . . C
  C9 0.02680(11) -0.2069(3) 0.34521(11) 0.0548(5) Uani d . 1 . . C
  C10 -0.02120(12) -0.1530(3) 0.37617(11) 0.0586(5) Uani d . 1 . . C
  C11 -0.01392(10) 0.0186(3) 0.41116(10) 0.0521(5) Uani d . 1 . . C
  C12 0.04097(9) 0.1392(2) 0.41314(9) 0.0416(4) Uani d . 1 . . C
  C13 0.28201(10) 0.3714(3) 0.40770(11) 0.0505(5) Uani d . 1 . . C
  C14 0.27049(9) 0.5347(3) 0.45099(9) 0.0469(4) Uani d . 1 . . C
  N1 0.14675(8) 0.2131(2) 0.38561(8) 0.0439(4) Uani d . 1 . . N
  O1 0.22098(8) 0.5375(2) 0.47297(7) 0.0607(4) Uani d . 1 . . O
  O2 0.31588(8) 0.6732(2) 0.46169(9) 0.0640(4) Uani d . 1 . . O
  Cl1 0.04921(3) 0.35561(7) 0.45803(3) 0.0600(2) Uani d . 1 . . Cl
  Cl2 0.14508(3) -0.16736(7) 0.31430(3) 0.0620(2) Uani d . 1 . . Cl
  H1 0.3026(16) 0.775(5) 0.4823(17) 0.099(10) Uiso d . 1 . . H
  H1N 0.1553(11) 0.281(3) 0.4167(11) 0.050(6) Uiso d . 1 . . H
  H2 0.2816(12) 0.503(3) 0.2848(10) 0.054(5) Uiso d . 1 . . H
  H3 0.1970(11) 0.498(3) 0.1708(12) 0.062(6) Uiso d . 1 . . H
  H4 0.0887(12) 0.364(3) 0.1572(13) 0.064(6) Uiso d . 1 . . H
  H5 0.0673(12) 0.230(3) 0.2518(11) 0.056(5) Uiso d . 1 . . H
  H9 0.0251(12) -0.328(4) 0.3222(12) 0.068(6) Uiso d . 1 . . H
  H10 -0.0606(14) -0.232(4) 0.3711(12) 0.074(7) Uiso d . 1 . . H
  H11 -0.0457(12) 0.054(3) 0.4328(11) 0.056(5) Uiso d . 1 . . H
  H13A 0.2803(11) 0.253(4) 0.4329(11) 0.060(6) Uiso d . 1 . . H
  H13B 0.3251(13) 0.381(3) 0.4015(11) 0.061(6) Uiso d . 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
  C1 0.0373(8) 0.0317(8) 0.0505(9) -0.0001(6) 0.0183(7) -0.0081(7)
  C2 0.0484(10) 0.0341(9) 0.0657(12) -0.0077(8) 0.0324(9) -0.0083(8)
  C3 0.0719(13) 0.0389(10) 0.0552(11) -0.0066(9) 0.0338(10) -0.0002(8)
  C4 0.0614(12) 0.0425(10) 0.0454(10) -0.0035(8) 0.0139(9) 0.0030(8)
  C5 0.0405(9) 0.0415(9) 0.0487(9) -0.0063(7) 0.0127(7) 0.0003(7)
  C6 0.0385(8) 0.0303(8) 0.0457(9) -0.0018(6) 0.0189(7) -0.0032(6)
  C7 0.0400(8) 0.0380(9) 0.0367(8) -0.0010(7) 0.0138(7) 0.0043(7)
  C8 0.0500(9) 0.0390(9) 0.0467(9) 0.0023(8) 0.0225(8) 0.0043(7)
  C9 0.0697(12) 0.0396(10) 0.0581(11) -0.0115(9) 0.0255(10) 0.0006(9)
  C10 0.0585(12) 0.0571(12) 0.0646(12) -0.0163(10) 0.0265(10) 0.0075(9)
  C11 0.0480(10) 0.0624(12) 0.0536(10) -0.0003(9) 0.0272(9) 0.0118(9)
  C12 0.0457(9) 0.0413(9) 0.0387(8) 0.0048(7) 0.0155(7) 0.0058(7)
  C13 0.0366(9) 0.0493(11) 0.0627(12) -0.0029(8) 0.0129(8) -0.0078(9)
  C14 0.0423(9) 0.0500(11) 0.0422(9) -0.0101(8) 0.0059(7) -0.0054(8)
  N1 0.0456(8) 0.0468(9) 0.0415(8) -0.0110(7) 0.0177(6) -0.0065(7)
  O1 0.0655(8) 0.0605(9) 0.0640(8) -0.0227(7) 0.0321(7) -0.0213(7)
  O2 0.0580(8) 0.0611(9) 0.0770(10) -0.0227(7) 0.0280(7) -0.0236(7)
  Cl1 0.0714(4) 0.0545(3) 0.0610(3) 0.0040(2) 0.0314(3) -0.0103(2)
  Cl2 0.0725(4) 0.0480(3) 0.0793(4) 0.0092(2) 0.0437(3) -0.0030(2)
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
  C1 C2 . 1.391(3) ?
  C1 C6 . 1.404(2) ?
  C1 C13 . 1.515(3) ?
  C2 C3 . 1.377(3) ?
  C3 C4 . 1.384(3) ?
  C4 C5 . 1.383(3) ?
  C5 C6 . 1.390(2) ?
  C6 N1 . 1.419(2) ?
  C7 N1 . 1.398(2) ?
  C7 C12 . 1.397(2) ?
  C7 C8 . 1.404(2) ?
  C8 C9 . 1.391(3) ?
  C8 Cl2 . 1.7301(18) ?
  C9 C10 . 1.374(3) ?
  C10 C11 . 1.374(3) ?
  C11 C12 . 1.387(3) ?
  C12 Cl1 . 1.7414(18) ?
  C13 C14 . 1.501(3) ?
  C14 O1 . 1.226(2) ?
  C14 O2 . 1.304(2) ?