#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012685.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_2012685
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o301
_journal_page_last  o304
_publ_section_title
;
Three isomeric bis(methoxycarbonyl)[2.2]paracyclophanes
;
loop_
_publ_author_name
  'Jones, Peter G.'
  'Hillmer, J\"org'
  'Hopf, Henning'
_chemical_formula_moiety  'C20 H20 O4'
_chemical_formula_sum  'C20 H20 O4'
_chemical_formula_weight  324.36
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
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  8.096(4)
_cell_length_b  21.282(11)
_cell_length_c  9.281(5)
_cell_angle_alpha  90
_cell_angle_beta  95.28(4)
_cell_angle_gamma  90
_cell_volume  1592.3(14)
_cell_formula_units_Z  4
_cell_measurement_temperature  178(2)
_exptl_crystal_density_diffrn  1.353
_diffrn_ambient_temperature  178(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 0.0866(2) 0.62940(8) 0.40719(18) 0.0358(4) Uani d . 1 . . C
  H1A -0.0063 0.6368 0.3321 0.043 Uiso calc R 1 . . H
  H1B 0.1521 0.5934 0.3757 0.043 Uiso calc R 1 . . H
  C2 0.2011(2) 0.69008(8) 0.42176(18) 0.0349(4) Uani d . 1 . . C
  H2A 0.2983 0.6835 0.3663 0.042 Uiso calc R 1 . . H
  H2B 0.1381 0.7264 0.3787 0.042 Uiso calc R 1 . . H
  C3 0.2608(2) 0.70523(7) 0.57705(17) 0.0289(4) Uani d . 1 . . C
  C4 0.36897(19) 0.66654(7) 0.66698(17) 0.0261(3) Uani d . 1 . . C
  C5 0.36049(19) 0.66757(7) 0.81608(18) 0.0286(4) Uani d . 1 . . C
  H5 0.4335 0.6414 0.8755 0.034 Uiso calc R 1 . . H
  C6 0.2487(2) 0.70560(8) 0.88108(18) 0.0321(4) Uani d . 1 . . C
  C7 0.1717(2) 0.75331(8) 0.7957(2) 0.0343(4) Uani d . 1 . . C
  H7 0.1149 0.7862 0.8395 0.041 Uiso calc R 1 . . H
  C8 0.1786(2) 0.75250(7) 0.64735(19) 0.0333(4) Uani d . 1 . . C
  H8 0.1255 0.7853 0.5910 0.040 Uiso calc R 1 . . H
  C9 0.1892(2) 0.68582(9) 1.02364(19) 0.0395(4) Uani d . 1 . . C
  H9A 0.1627 0.7237 1.0789 0.047 Uiso calc R 1 . . H
  H9B 0.2793 0.6630 1.0808 0.047 Uiso calc R 1 . . H
  C10 0.0297(2) 0.64211(9) 1.00303(18) 0.0354(4) Uani d . 1 . . C
  H10A 0.0451 0.6059 1.0699 0.042 Uiso calc R 1 . . H
  H10B -0.0679 0.6661 1.0292 0.042 Uiso calc R 1 . . H
  C11 -0.00429(19) 0.61792(7) 0.84983(17) 0.0274(4) Uani d . 1 . . C
  C12 -0.10858(19) 0.65368(8) 0.75372(18) 0.0304(4) Uani d . 1 . . C
  H12 -0.1895 0.6800 0.7910 0.036 Uiso calc R 1 . . H
  C13 -0.09777(19) 0.65202(8) 0.60648(18) 0.0304(4) Uani d . 1 . . C
  H13 -0.1696 0.6774 0.5443 0.036 Uiso calc R 1 . . H
  C14 0.01797(19) 0.61324(7) 0.54809(17) 0.0284(4) Uani d . 1 . . C
  C15 0.09165(18) 0.56707(7) 0.63868(17) 0.0257(3) Uani d . 1 . . C
  H15 0.1494 0.5336 0.5979 0.031 Uiso calc R 1 . . H
  C16 0.08267(19) 0.56879(7) 0.78843(17) 0.0256(3) Uani d . 1 . . C
  C17 0.47406(19) 0.61790(7) 0.60409(18) 0.0277(4) Uani d . 1 . . C
  C18 0.6381(2) 0.52648(8) 0.6598(2) 0.0368(4) Uani d . 1 . . C
  H18A 0.5700 0.4905 0.6250 0.044 Uiso calc R 1 . . H
  H18B 0.7148 0.5134 0.7422 0.044 Uiso calc R 1 . . H
  H18C 0.7015 0.5418 0.5819 0.044 Uiso calc R 1 . . H
  C19 0.1892(2) 0.52461(7) 0.87962(18) 0.0306(4) Uani d . 1 . . C
  C20 0.3453(2) 0.43088(9) 0.8791(2) 0.0493(5) Uani d . 1 . . C
  H20A 0.4503 0.4530 0.9034 0.059 Uiso calc R 1 . . H
  H20B 0.3638 0.3952 0.8160 0.059 Uiso calc R 1 . . H
  H20C 0.3023 0.4157 0.9681 0.059 Uiso calc R 1 . . H
  O1 0.50458(16) 0.61564(6) 0.47945(13) 0.0393(3) Uani d . 1 . . O
  O2 0.53199(14) 0.57609(5) 0.70449(12) 0.0350(3) Uani d . 1 . . O
  O3 0.24102(18) 0.53320(7) 1.00414(14) 0.0504(4) Uani d . 1 . . O
  O4 0.22660(16) 0.47329(5) 0.80545(14) 0.0406(3) Uani d . 1 . . O
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 0.0401(10) 0.0392(10) 0.0270(9) -0.0010(8) -0.0022(7) 0.0005(7)
  C2 0.0357(9) 0.0376(9) 0.0315(9) 0.0017(7) 0.0039(7) 0.0090(7)
  C3 0.0284(8) 0.0248(8) 0.0339(9) -0.0050(6) 0.0050(7) 0.0049(7)
  C4 0.0231(8) 0.0238(8) 0.0313(8) -0.0065(6) 0.0018(6) -0.0003(6)
  C5 0.0250(8) 0.0276(8) 0.0324(9) -0.0062(6) -0.0026(6) -0.0025(7)
  C6 0.0301(9) 0.0334(9) 0.0322(9) -0.0079(7) 0.0005(7) -0.0103(7)
  C7 0.0310(9) 0.0256(8) 0.0467(10) -0.0046(7) 0.0053(7) -0.0102(7)
  C8 0.0313(9) 0.0218(8) 0.0465(10) -0.0019(7) 0.0029(7) 0.0024(7)
  C9 0.0402(10) 0.0466(11) 0.0317(9) -0.0045(8) 0.0025(7) -0.0113(8)
  C10 0.0376(9) 0.0386(10) 0.0314(9) -0.0003(8) 0.0107(7) -0.0033(7)
  C11 0.0239(8) 0.0273(8) 0.0316(8) -0.0041(6) 0.0052(6) 0.0000(6)
  C12 0.0226(8) 0.0260(8) 0.0429(10) -0.0006(6) 0.0046(7) -0.0023(7)
  C13 0.0246(8) 0.0275(8) 0.0375(9) -0.0008(6) -0.0054(7) 0.0031(7)
  C14 0.0264(8) 0.0287(8) 0.0289(8) -0.0061(6) -0.0035(6) -0.0021(6)
  C15 0.0217(7) 0.0230(8) 0.0317(8) -0.0035(6) -0.0007(6) -0.0029(6)
  C16 0.0217(7) 0.0237(8) 0.0312(8) -0.0036(6) 0.0015(6) 0.0011(6)
  C17 0.0232(8) 0.0268(8) 0.0328(9) -0.0062(6) 0.0010(6) 0.0006(7)
  C18 0.0330(9) 0.0285(9) 0.0477(11) 0.0052(7) -0.0019(8) -0.0035(7)
  C19 0.0272(8) 0.0284(9) 0.0360(9) -0.0039(7) 0.0023(7) 0.0055(7)
  C20 0.0418(11) 0.0307(10) 0.0735(14) 0.0082(8) -0.0043(10) 0.0127(9)
  O1 0.0445(7) 0.0407(7) 0.0336(7) 0.0055(6) 0.0082(5) -0.0013(5)
  O2 0.0326(6) 0.0331(6) 0.0392(7) 0.0059(5) 0.0035(5) 0.0030(5)
  O3 0.0589(9) 0.0533(9) 0.0366(8) 0.0130(7) -0.0084(6) 0.0059(6)
  O4 0.0413(7) 0.0259(6) 0.0526(8) 0.0068(5) -0.0071(6) 0.0020(5)
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 . 1.588(3) n
  C9 C10 . 1.588(3) n
  C1 C14 . 1.507(2) ?
  C1 H1A . 0.9900 ?
  C1 H1B . 0.9900 ?
  C2 C3 . 1.512(2) ?
  C2 H2A . 0.9900 ?
  C2 H2B . 0.9900 ?
  C3 C8 . 1.400(2) ?
  C3 C4 . 1.417(2) ?
  C4 C5 . 1.392(2) ?
  C4 C17 . 1.492(2) ?
  C5 C6 . 1.393(2) ?
  C5 H5 . 0.9500 ?
  C6 C7 . 1.399(3) ?
  C6 C9 . 1.509(3) ?
  C7 C8 . 1.383(3) ?
  C7 H7 . 0.9500 ?
  C8 H8 . 0.9500 ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C10 C11 . 1.513(2) ?
  C10 H10A . 0.9900 ?
  C10 H10B . 0.9900 ?
  C11 C12 . 1.396(2) ?
  C11 C16 . 1.410(2) ?
  C12 C13 . 1.378(2) ?
  C12 H12 . 0.9500 ?
  C13 C14 . 1.395(2) ?
  C13 H13 . 0.9500 ?
  C14 C15 . 1.391(2) ?
  C15 C16 . 1.399(2) ?
  C15 H15 . 0.9500 ?
  C16 C19 . 1.487(2) ?
  C17 O1 . 1.206(2) ?
  C17 O2 . 1.341(2) ?
  C18 O2 . 1.446(2) ?
  C18 H18A . 0.9800 ?
  C18 H18B . 0.9800 ?
  C18 H18C . 0.9800 ?
  C19 O3 . 1.206(2) ?
  C19 O4 . 1.341(2) ?
  C20 O4 . 1.444(2) ?
  C20 H20A . 0.9800 ?
  C20 H20B . 0.9800 ?
  C20 H20C . 0.9800 ?