#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008962.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_2008962
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
Dimethyl 2-(5,8-dichloro-10-oxotricyclo[7.3.2.0^2,7^]tetradeca-2(7),3,5,11-
tetraen-6-ylmethyl)malonate
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Meinhardt, Sven'
  'Sch\"urmann, Markus'
  'Preut, Hans'
  'Eilbracht, Peter'
_chemical_formula_sum  'C20 H20 Cl2 O5'
_chemical_formula_weight  411.26
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  8.0430(10)
_cell_length_b  13.288(2)
_cell_length_c  17.629(2)
_cell_angle_alpha  90.00
_cell_angle_beta  96.34(3)
_cell_angle_gamma  90.00
_cell_volume  1872.6(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  291.0(10)
_exptl_crystal_density_diffrn  1.459
_diffrn_ambient_temperature  291(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 0.11929(6) 0.03109(3) 0.09693(3) 0.04978(15) Uani d . 1 . . Cl
  Cl2 -0.16248(8) 0.29302(5) -0.15086(3) 0.06745(19) Uani d . 1 . . Cl
  O1 0.25331(16) 0.50285(9) -0.02365(7) 0.0435(3) Uani d . 1 . . O
  O2 0.2749(2) 0.37200(11) -0.10147(9) 0.0646(4) Uani d . 1 . . O
  O3 0.30135(18) 0.33035(13) 0.11415(9) 0.0623(4) Uani d . 1 . . O
  O4 0.08976(17) 0.43620(11) 0.12275(7) 0.0511(3) Uani d . 1 . . O
  O5 -0.0919(2) 0.28758(11) 0.24133(10) 0.0667(4) Uani d . 1 . . O
  C1 -0.0633(2) 0.12039(13) 0.19961(9) 0.0386(4) Uani d . 1 . . C
  H1 0.036(3) 0.1270(14) 0.2331(11) 0.042(5) Uiso d . 1 . . H
  C2 -0.1651(2) 0.21118(13) 0.22052(9) 0.0425(4) Uani d . 1 . . C
  C3 -0.3476(3) 0.20536(15) 0.21717(11) 0.0494(4) Uani d . 1 . . C
  H3 -0.395(3) 0.2549(19) 0.2485(14) 0.067(7) Uiso d . 1 . . H
  C4 -0.4432(2) 0.14356(15) 0.17283(11) 0.0472(4) Uani d . 1 . . C
  H4 -0.562(3) 0.1496(19) 0.1726(14) 0.071(7) Uiso d . 1 . . H
  C5 -0.3856(2) 0.06915(13) 0.11658(10) 0.0396(4) Uani d . 1 . . C
  H5 -0.485(3) 0.0370(14) 0.0940(11) 0.038(5) Uiso d . 1 . . H
  C6 -0.2740(3) -0.01562(13) 0.15266(12) 0.0464(4) Uani d . 1 . . C
  H6A -0.343(3) -0.0664(18) 0.1736(13) 0.061(6) Uiso d . 1 . . H
  H6B -0.225(3) -0.0472(15) 0.1116(12) 0.041(5) Uiso d . 1 . . H
  C7 -0.1427(3) 0.01928(14) 0.21517(11) 0.0476(4) Uani d . 1 . . C
  H7A -0.055(3) -0.0337(18) 0.2203(13) 0.061(6) Uiso d . 1 . . H
  H7B -0.188(3) 0.0256(16) 0.2632(14) 0.056(6) Uiso d . 1 . . H
  C8 -0.01237(19) 0.13653(11) 0.11905(9) 0.0316(3) Uani d . 1 . . C
  H8 0.063(2) 0.1913(13) 0.1234(10) 0.028(4) Uiso d . 1 . . H
  C9 -0.14563(18) 0.15624(11) 0.05302(8) 0.0290(3) Uani d . 1 . . C
  C10 -0.31266(19) 0.12573(11) 0.05269(9) 0.0318(3) Uani d . 1 . . C
  C11 -0.4270(2) 0.15030(14) -0.00959(10) 0.0402(4) Uani d . 1 . . C
  H11 -0.542(3) 0.1285(14) -0.0076(11) 0.043(5) Uiso d . 1 . . H
  C12 -0.3819(2) 0.20183(14) -0.07121(10) 0.0430(4) Uani d . 1 . . C
  H12 -0.464(3) 0.2182(15) -0.1125(13) 0.052(6) Uiso d . 1 . . H
  C13 -0.2171(2) 0.22965(13) -0.07091(9) 0.0388(4) Uani d . 1 . . C
  C14 -0.09543(19) 0.20944(11) -0.01009(9) 0.0312(3) Uani d . 1 . . C
  C15 0.0817(2) 0.24470(12) -0.01570(10) 0.0363(3) Uani d . 1 . . C
  H15B 0.102(2) 0.2346(14) -0.0677(12) 0.040(5) Uiso d . 1 . . H
  H15A 0.160(2) 0.2061(14) 0.0176(11) 0.039(5) Uiso d . 1 . . H
  C16 0.1064(2) 0.35728(12) 0.00369(9) 0.0334(3) Uani d . 1 . . C
  H16 0.003(2) 0.3910(14) -0.0053(11) 0.040(5) Uiso d . 1 . . H
  C17 0.2220(2) 0.40875(13) -0.04741(10) 0.0380(4) Uani d . 1 . . C
  C18 0.3487(3) 0.56516(18) -0.07000(14) 0.0551(5) Uani d . 1 . . C
  H18A 0.381(4) 0.621(2) -0.0397(17) 0.092(9) Uiso d . 1 . . H
  H18B 0.435(3) 0.5299(19) -0.0840(15) 0.065(7) Uiso d . 1 . . H
  H18C 0.276(3) 0.5796(18) -0.1203(15) 0.065(7) Uiso d . 1 . . H
  C19 0.1783(2) 0.37256(12) 0.08607(10) 0.0382(4) Uani d . 1 . . C
  C20 0.1534(4) 0.4559(2) 0.20169(13) 0.0674(7) Uani d . 1 . . C
  H20A 0.075(4) 0.500(2) 0.220(2) 0.102(11) Uiso d . 1 . . H
  H20B 0.254(4) 0.487(2) 0.2012(17) 0.083(9) Uiso d . 1 . . H
  H20C 0.161(3) 0.395(2) 0.2274(15) 0.072(8) 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 0.0429(3) 0.0460(3) 0.0592(3) 0.01623(18) 0.0000(2) -0.00451(19)
  Cl2 0.0721(4) 0.0882(4) 0.0413(3) -0.0142(3) 0.0028(2) 0.0227(2)
  O1 0.0419(7) 0.0427(6) 0.0474(7) -0.0091(5) 0.0115(5) -0.0003(5)
  O2 0.0828(11) 0.0553(8) 0.0634(9) -0.0154(8) 0.0421(8) -0.0103(7)
  O3 0.0503(8) 0.0740(10) 0.0589(9) 0.0086(7) -0.0109(7) 0.0043(7)
  O4 0.0536(8) 0.0578(8) 0.0419(7) -0.0015(6) 0.0053(6) -0.0134(6)
  O5 0.0693(10) 0.0540(9) 0.0778(11) -0.0114(7) 0.0134(8) -0.0278(8)
  C1 0.0414(9) 0.0405(9) 0.0318(8) -0.0014(7) -0.0059(7) 0.0010(6)
  C2 0.0538(10) 0.0430(9) 0.0312(8) -0.0034(8) 0.0068(7) -0.0056(6)
  C3 0.0550(11) 0.0506(11) 0.0456(10) 0.0027(9) 0.0189(8) -0.0046(8)
  C4 0.0399(9) 0.0554(11) 0.0486(10) -0.0002(8) 0.0145(8) 0.0060(8)
  C5 0.0360(8) 0.0410(9) 0.0416(8) -0.0109(7) 0.0034(7) 0.0029(7)
  C6 0.0538(11) 0.0338(9) 0.0514(10) -0.0082(8) 0.0049(9) 0.0058(8)
  C7 0.0566(11) 0.0415(10) 0.0435(10) 0.0001(8) 0.0005(8) 0.0105(7)
  C8 0.0288(7) 0.0297(7) 0.0355(8) 0.0017(6) -0.0007(6) -0.0034(6)
  C9 0.0285(7) 0.0271(7) 0.0308(7) 0.0011(5) 0.0012(5) -0.0042(5)
  C10 0.0308(7) 0.0312(7) 0.0331(7) -0.0020(6) 0.0021(6) -0.0027(6)
  C11 0.0303(8) 0.0459(9) 0.0429(9) -0.0039(7) -0.0032(7) -0.0024(7)
  C12 0.0396(9) 0.0496(10) 0.0368(8) -0.0002(7) -0.0091(7) 0.0006(7)
  C13 0.0457(9) 0.0389(8) 0.0317(8) -0.0028(7) 0.0034(7) 0.0020(6)
  C14 0.0317(7) 0.0296(7) 0.0326(7) -0.0001(6) 0.0047(6) -0.0052(6)
  C15 0.0338(8) 0.0359(8) 0.0411(9) -0.0008(6) 0.0121(7) -0.0027(7)
  C16 0.0271(7) 0.0361(8) 0.0376(8) -0.0001(6) 0.0067(6) -0.0009(6)
  C17 0.0327(8) 0.0410(8) 0.0412(8) -0.0019(7) 0.0079(7) 0.0019(7)
  C18 0.0566(13) 0.0505(12) 0.0608(13) -0.0151(10) 0.0184(11) 0.0045(10)
  C19 0.0338(8) 0.0379(8) 0.0428(9) -0.0079(6) 0.0041(7) 0.0019(7)
  C20 0.091(2) 0.0672(16) 0.0427(11) -0.0202(14) 0.0015(12) -0.0133(11)
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 C8 . 1.8242(15) ?
  Cl2 C13 . 1.7392(17) ?
  O1 C17 . 1.334(2) ?
  O1 C18 . 1.442(2) ?
  O2 C17 . 1.191(2) ?
  O3 C19 . 1.196(2) ?
  O4 C19 . 1.320(2) ?
  O4 C20 . 1.453(3) ?
  O5 C2 . 1.210(2) ?
  C1 C7 . 1.525(2) ?
  C1 C2 . 1.526(3) ?
  C1 C8 . 1.536(2) ?
  C1 H1 . 0.95(2) ?
  C2 C3 . 1.464(3) ?
  C3 C4 . 1.321(3) ?
  C3 H3 . 0.97(3) ?
  C4 C5 . 1.509(3) ?
  C4 H4 . 0.96(3) ?
  C5 C10 . 1.525(2) ?
  C5 C6 . 1.534(3) ?
  C5 H5 . 0.95(2) ?
  C6 C7 . 1.513(3) ?
  C6 H6A . 0.97(2) ?
  C6 H6B . 0.96(2) ?
  C7 H7A . 1.00(2) ?
  C7 H7B . 0.96(2) ?
  C8 C9 . 1.515(2) ?
  C8 H8 . 0.943(18) ?
  C9 C10 . 1.403(2) ?
  C9 C14 . 1.414(2) ?
  C10 C11 . 1.391(2) ?
  C11 C12 . 1.367(3) ?
  C11 H11 . 0.97(2) ?
  C12 C13 . 1.376(3) ?
  C12 H12 . 0.95(2) ?
  C13 C14 . 1.395(2) ?
  C14 C15 . 1.513(2) ?
  C15 C16 . 1.543(2) ?
  C15 H15B . 0.96(2) ?
  C15 H15A . 0.96(2) ?
  C16 C19 . 1.516(2) ?
  C16 C17 . 1.526(2) ?
  C16 H16 . 0.944(19) ?
  C18 H18A . 0.94(3) ?
  C18 H18B . 0.90(3) ?
  C18 H18C . 1.03(3) ?
  C20 H20A . 0.94(4) ?
  C20 H20B . 0.91(3) ?
  C20 H20C . 0.93(3) ?