#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202588.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_2202588
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1670
_journal_page_last  o1671
_publ_section_title
;
7-Chloromethylbenzo[b]naphtho[1,2-d]pyran-6-one
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Hoong-Kun Fun'
  'Hua-You Hu'
  'Jian-Hua Xu'
  'Xue-Mei Li'
  'Shu-Sheng Zhang'
_chemical_formula_moiety  'C18 H11 Cl O2'
_chemical_formula_sum  'C18 H11 Cl O2'
_chemical_formula_iupac  'C18 H11 Cl O2'
_chemical_formula_weight  294.72
_symmetry_cell_setting  monoclinic
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  9.9771(5)
_cell_length_b  16.1368(8)
_cell_length_c  8.2899(4)
_cell_angle_alpha  90.00
_cell_angle_beta  98.1290(10)
_cell_angle_gamma  90.00
_cell_volume  1321.25(11)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.482
_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
  Cl1 0.57400(5) 0.04931(3) 0.69791(6) 0.0606(2) Uani d . 1 . . Cl
  O1 1.06207(12) -0.02294(8) 0.68746(15) 0.0491(3) Uani d . 1 . . O
  O2 0.91060(16) 0.07091(9) 0.7126(2) 0.0739(5) Uani d . 1 . . O
  C1 1.12861(17) -0.09531(10) 0.7363(2) 0.0415(4) Uani d . 1 . . C
  C2 1.25689(19) -0.10377(13) 0.6925(2) 0.0521(5) Uani d . 1 . . C
  C3 1.3334(2) -0.17165(13) 0.7473(2) 0.0547(5) Uani d . 1 . . C
  C4 1.28303(18) -0.22966(12) 0.8453(2) 0.0502(4) Uani d . 1 . . C
  C5 1.15440(17) -0.22109(11) 0.8863(2) 0.0426(4) Uani d . 1 . . C
  C6 1.07073(16) -0.15433(10) 0.82790(18) 0.0361(4) Uani d . 1 . . C
  C7 0.93398(15) -0.13882(9) 0.86682(17) 0.0336(3) Uani d . 1 . . C
  C8 0.88200(16) -0.05866(9) 0.84402(19) 0.0363(4) Uani d . 1 . . C
  C9 0.94942(17) 0.00196(10) 0.7489(2) 0.0446(4) Uani d . 1 . . C
  C10 0.85193(15) -0.20265(10) 0.92574(18) 0.0346(3) Uani d . 1 . . C
  C11 0.87364(17) -0.28889(10) 0.9083(2) 0.0401(4) Uani d . 1 . . C
  C12 0.78871(19) -0.34572(11) 0.9626(2) 0.0464(4) Uani d . 1 . . C
  C13 0.67945(19) -0.32074(12) 1.0397(2) 0.0496(4) Uani d . 1 . . C
  C14 0.65283(18) -0.23876(12) 1.0537(2) 0.0464(4) Uani d . 1 . . C
  C15 0.73459(16) -0.17806(10) 0.99271(18) 0.0381(4) Uani d . 1 . . C
  C16 0.69621(17) -0.09338(11) 0.9865(2) 0.0427(4) Uani d . 1 . . C
  C17 0.75984(16) -0.03556(10) 0.90550(19) 0.0387(4) Uani d . 1 . . C
  C18 0.6941(2) 0.04808(11) 0.8831(2) 0.0474(4) Uani d . 1 . . C
  H2 1.289(2) -0.0601(13) 0.627(3) 0.060(6) Uiso d . 1 . . H
  H3 1.419(3) -0.1773(14) 0.716(3) 0.071(7) Uiso d . 1 . . H
  H4 1.336(2) -0.2761(14) 0.887(3) 0.058(6) Uiso d . 1 . . H
  H5 1.1245(19) -0.2597(12) 0.960(2) 0.047(5) Uiso d . 1 . . H
  H11 0.943(2) -0.3080(12) 0.851(2) 0.048(5) Uiso d . 1 . . H
  H12 0.802(2) -0.4021(13) 0.944(2) 0.054(5) Uiso d . 1 . . H
  H13 0.624(2) -0.3615(13) 1.080(2) 0.057(6) Uiso d . 1 . . H
  H14 0.577(2) -0.2189(13) 1.099(3) 0.057(6) Uiso d . 1 . . H
  H16 0.622(2) -0.0759(12) 1.037(2) 0.053(5) Uiso d . 1 . . H
  H18B 0.758(2) 0.0941(13) 0.869(2) 0.055(5) Uiso d . 1 . . H
  H18A 0.633(2) 0.0568(13) 0.978(3) 0.068(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
  Cl1 0.0518(3) 0.0569(3) 0.0683(3) 0.0071(2) -0.0085(2) 0.0093(2)
  O1 0.0470(7) 0.0465(7) 0.0557(7) 0.0012(5) 0.0141(6) 0.0126(5)
  O2 0.0686(10) 0.0438(8) 0.1143(13) 0.0092(7) 0.0298(9) 0.0281(8)
  C1 0.0411(9) 0.0423(9) 0.0408(8) -0.0002(7) 0.0044(7) -0.0012(7)
  C2 0.0485(10) 0.0598(12) 0.0513(10) -0.0041(9) 0.0182(8) -0.0012(9)
  C3 0.0398(10) 0.0665(12) 0.0606(11) 0.0030(9) 0.0168(9) -0.0127(9)
  C4 0.0412(9) 0.0491(10) 0.0595(11) 0.0080(8) 0.0047(8) -0.0088(8)
  C5 0.0387(9) 0.0408(9) 0.0476(10) 0.0022(7) 0.0035(7) -0.0013(7)
  C6 0.0351(8) 0.0370(8) 0.0357(8) -0.0013(6) 0.0031(6) -0.0035(6)
  C7 0.0340(8) 0.0343(8) 0.0312(7) 0.0010(6) -0.0003(6) -0.0022(6)
  C8 0.0358(8) 0.0349(8) 0.0364(8) 0.0005(6) -0.0008(6) -0.0022(6)
  C9 0.0404(9) 0.0382(9) 0.0543(10) -0.0004(7) 0.0037(7) 0.0057(7)
  C10 0.0332(8) 0.0369(8) 0.0324(7) 0.0009(6) -0.0001(6) 0.0008(6)
  C11 0.0395(9) 0.0372(9) 0.0421(9) 0.0023(7) 0.0012(7) 0.0005(7)
  C12 0.0499(10) 0.0378(9) 0.0488(10) -0.0031(7) -0.0018(8) 0.0029(7)
  C13 0.0462(10) 0.0521(10) 0.0488(10) -0.0111(8) 0.0012(8) 0.0099(8)
  C14 0.0383(9) 0.0570(11) 0.0444(9) -0.0009(8) 0.0069(7) 0.0058(8)
  C15 0.0354(8) 0.0441(9) 0.0341(8) 0.0003(6) 0.0020(6) 0.0004(6)
  C16 0.0361(9) 0.0509(10) 0.0418(9) 0.0070(7) 0.0078(7) -0.0039(7)
  C17 0.0376(9) 0.0383(8) 0.0388(8) 0.0036(6) 0.0005(6) -0.0055(6)
  C18 0.0481(10) 0.0406(10) 0.0524(10) 0.0083(8) 0.0028(8) -0.0069(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
  Cl1 C18 . 1.8090(19) ?
  O1 C9 . 1.358(2) yes
  O1 C1 . 1.376(2) yes
  O2 C9 . 1.202(2) ?
  C1 C2 . 1.386(2) ?
  C1 C6 . 1.393(2) ?
  C2 C3 . 1.375(3) ?
  C2 H2 . 0.97(2) ?
  C3 C4 . 1.380(3) ?
  C3 H3 . 0.93(2) ?
  C4 C5 . 1.380(2) ?
  C4 H4 . 0.95(2) ?
  C5 C6 . 1.406(2) ?
  C5 H5 . 0.95(2) ?
  C6 C7 . 1.467(2) yes
  C7 C8 . 1.397(2) ?
  C7 C10 . 1.443(2) ?
  C8 C17 . 1.435(2) ?
  C8 C9 . 1.477(2) yes
  C10 C15 . 1.421(2) ?
  C10 C11 . 1.419(2) ?
  C11 C12 . 1.368(3) ?
  C11 H11 . 0.95(2) ?
  C12 C13 . 1.398(3) ?
  C12 H12 . 0.94(2) ?
  C13 C14 . 1.358(3) ?
  C13 H13 . 0.95(2) ?
  C14 C15 . 1.413(2) ?
  C14 H14 . 0.94(2) ?
  C15 C16 . 1.418(2) ?
  C16 C17 . 1.358(2) ?
  C16 H16 . 0.95(2) ?
  C17 C18 . 1.501(2) yes
  C18 H18B . 1.00(2) ?
  C18 H18A . 1.07(2) ?