#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012686.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_2012686
_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
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
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
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  7.470(3)
_cell_length_b  11.287(4)
_cell_length_c  9.494(3)
_cell_angle_alpha  90
_cell_angle_beta  90.83(3)
_cell_angle_gamma  90
_cell_volume  800.4(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  178(2)
_exptl_crystal_density_diffrn  1.346
_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 0.5437(3) 0.0772(2) 0.2707(2) 0.0294(5) Uani d . 1 . . C
  H1A 0.6320 0.0196 0.3085 0.037 Uiso calc R 1 . . H
  H1B 0.5982 0.1176 0.1893 0.037 Uiso calc R 1 . . H
  C2 0.3700(3) 0.0077(2) 0.2183(3) 0.0313(5) Uani d . 1 . . C
  H2A 0.3289 0.0408 0.1268 0.037 Uiso calc R 1 . . H
  H2B 0.4008 -0.0767 0.2034 0.037 Uiso calc R 1 . . H
  C3 0.2194(3) 0.0161(2) 0.3235(2) 0.0276(5) Uani d . 1 . . C
  C4 0.0804(3) 0.1003(2) 0.3116(2) 0.0248(5) Uani d . 1 . . C
  C5 -0.0026(3) 0.1431(2) 0.4320(2) 0.0269(5) Uani d . 1 . . C
  H5 -0.0937 0.2014 0.4227 0.032 Uiso calc R 1 . . H
  C6 0.0455(3) 0.1018(2) 0.5664(2) 0.0281(5) Uani d . 1 . . C
  C7 0.1514(3) 0.0001(2) 0.5719(3) 0.0320(5) Uani d . 1 . . C
  H7 0.1649 -0.0416 0.6583 0.037 Uiso calc R 1 . . H
  C8 0.2376(3) -0.0412(2) 0.4527(3) 0.0316(5) Uani d . 1 . . C
  H8 0.3104 -0.1100 0.4597 0.036 Uiso calc R 1 . . H
  C9 0.0175(3) 0.1779(3) 0.6944(3) 0.0354(6) Uani d . 1 . . C
  H9A 0.0297 0.1282 0.7799 0.042 Uiso calc R 1 . . H
  H9B -0.1058 0.2101 0.6914 0.042 Uiso calc R 1 . . H
  C10 0.1551(3) 0.2845(2) 0.7049(2) 0.0329(5) Uani d . 1 . . C
  H10A 0.0917 0.3595 0.6835 0.040 Uiso calc R 1 . . H
  H10B 0.2027 0.2896 0.8026 0.040 Uiso calc R 1 . . H
  C11 0.3093(3) 0.2703(2) 0.6050(2) 0.0256(4) Uani d . 1 . . C
  C12 0.4446(3) 0.1881(2) 0.6329(2) 0.0278(5) Uani d . 1 . . C
  H12 0.4720 0.1665 0.7275 0.033 Uiso calc R 1 . . H
  C13 0.5397(3) 0.1373(2) 0.5234(2) 0.0264(5) Uani d . 1 . . C
  H13 0.6304 0.0807 0.5442 0.033 Uiso calc R 1 . . H
  C14 0.5039(3) 0.1681(2) 0.3833(2) 0.0252(4) Uani d . 1 . . C
  C15 0.4021(3) 0.2717(2) 0.3603(2) 0.0237(4) Uani d . 1 . . C
  C16 0.3042(3) 0.3201(2) 0.4709(2) 0.0240(4) Uani d . 1 . . C
  H16 0.2327 0.3884 0.4541 0.028 Uiso calc R 1 . . H
  C17 0.0250(3) 0.1511(2) 0.1720(2) 0.0274(5) Uani d . 1 . . C
  C18 -0.1126(4) 0.3139(3) 0.0560(3) 0.0404(6) Uani d . 1 . . C
  H18A -0.0271 0.3021 -0.0200 0.048 Uiso calc R 1 . . H
  H18B -0.1308 0.3990 0.0709 0.048 Uiso calc R 1 . . H
  H18C -0.2270 0.2767 0.0303 0.048 Uiso calc R 1 . . H
  C19 0.3844(3) 0.3235(2) 0.2166(2) 0.0274(5) Uani d . 1 . . C
  C20 0.3262(4) 0.4977(3) 0.0876(3) 0.0409(6) Uani d . 1 . . C
  H20A 0.4436 0.4984 0.0429 0.049 Uiso calc R 1 . . H
  H20B 0.2853 0.5793 0.1016 0.049 Uiso calc R 1 . . H
  H20C 0.2401 0.4555 0.0269 0.049 Uiso calc R 1 . . H
  O1 0.0330(3) 0.10000(18) 0.06044(18) 0.0417(5) Uani d . 1 . . O
  O2 -0.0430(2) 0.26074(16) 0.18452(17) 0.0336(4) Uani d . 1 . . O
  O3 0.4070(3) 0.2718(2) 0.10715(18) 0.0467(5) Uani d . 1 . . O
  O4 0.3401(2) 0.43852(16) 0.22215(18) 0.0338(4) 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 0.0252(11) 0.0285(12) 0.0347(12) 0.0014(9) 0.0050(9) -0.0049(10)
  C2 0.0299(12) 0.0287(12) 0.0354(13) 0.0047(10) 0.0009(9) -0.0076(10)
  C3 0.0256(11) 0.0234(11) 0.0338(12) -0.0057(9) -0.0027(9) -0.0046(9)
  C4 0.0225(10) 0.0225(10) 0.0294(11) -0.0036(9) -0.0026(8) -0.0021(9)
  C5 0.0193(10) 0.0297(12) 0.0317(11) -0.0032(9) 0.0000(8) 0.0027(10)
  C6 0.0208(10) 0.0325(12) 0.0312(11) -0.0073(9) 0.0035(8) 0.0044(10)
  C7 0.0294(11) 0.0316(12) 0.0349(12) -0.0076(10) -0.0021(9) 0.0108(11)
  C8 0.0263(11) 0.0231(11) 0.0452(14) -0.0021(10) -0.0028(10) 0.0026(11)
  C9 0.0307(11) 0.0470(15) 0.0287(11) -0.0028(12) 0.0068(9) 0.0052(11)
  C10 0.0361(12) 0.0360(13) 0.0267(11) 0.0024(11) 0.0032(9) -0.0030(10)
  C11 0.0256(10) 0.0229(10) 0.0284(11) -0.0032(9) -0.0002(8) -0.0025(9)
  C12 0.0267(11) 0.0299(12) 0.0268(11) -0.0043(10) -0.0040(9) 0.0026(9)
  C13 0.0209(10) 0.0244(11) 0.0338(11) 0.0003(9) -0.0016(8) 0.0015(9)
  C14 0.0193(9) 0.0243(10) 0.0322(11) -0.0033(9) 0.0020(8) 0.0001(10)
  C15 0.0217(9) 0.0218(10) 0.0276(10) -0.0041(9) -0.0009(8) 0.0000(9)
  C16 0.0233(10) 0.0204(10) 0.0283(11) -0.0026(9) -0.0013(8) -0.0022(9)
  C17 0.0243(10) 0.0294(12) 0.0285(11) -0.0039(10) -0.0009(8) -0.0030(10)
  C18 0.0531(16) 0.0387(14) 0.0292(12) 0.0080(13) 0.0000(11) 0.0054(11)
  C19 0.0279(11) 0.0266(11) 0.0276(11) -0.0021(10) 0.0023(8) 0.0015(10)
  C20 0.0519(15) 0.0379(14) 0.0327(13) 0.0005(13) -0.0043(11) 0.0105(12)
  O1 0.0512(11) 0.0421(11) 0.0313(9) 0.0071(9) -0.0109(8) -0.0123(8)
  O2 0.0442(10) 0.0291(9) 0.0274(8) 0.0055(8) -0.0007(7) 0.0008(7)
  O3 0.0744(13) 0.0374(10) 0.0283(9) 0.0073(11) 0.0043(8) -0.0014(9)
  O4 0.0463(10) 0.0264(9) 0.0286(9) 0.0034(8) -0.0016(7) 0.0049(7)
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 . 1.590(3) n
  C9 C10 . 1.584(4) n
  C1 C14 . 1.514(3) ?
  C1 H1A . 0.9900 ?
  C1 H1B . 0.9900 ?
  C2 C3 . 1.518(3) ?
  C2 H2A . 0.9900 ?
  C2 H2B . 0.9900 ?
  C3 C8 . 1.392(3) ?
  C3 C4 . 1.411(3) ?
  C4 C5 . 1.395(3) ?
  C4 C17 . 1.497(3) ?
  C5 C6 . 1.400(3) ?
  C5 H5 . 0.9500 ?
  C6 C7 . 1.395(4) ?
  C6 C9 . 1.505(4) ?
  C7 C8 . 1.390(4) ?
  C7 H7 . 0.9500 ?
  C8 H8 . 0.9500 ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C10 C11 . 1.511(3) ?
  C10 H10A . 0.9900 ?
  C10 H10B . 0.9900 ?
  C11 C16 . 1.391(3) ?
  C11 C12 . 1.395(3) ?
  C12 C13 . 1.391(3) ?
  C12 H12 . 0.9500 ?
  C13 C14 . 1.397(3) ?
  C13 H13 . 0.9500 ?
  C14 C15 . 1.410(3) ?
  C15 C16 . 1.400(3) ?
  C15 C19 . 1.488(3) ?
  C16 H16 . 0.9500 ?
  C17 O1 . 1.208(3) ?
  C17 O2 . 1.344(3) ?
  C18 O2 . 1.449(3) ?
  C18 H18A . 0.9800 ?
  C18 H18B . 0.9800 ?
  C18 H18C . 0.9800 ?
  C19 O3 . 1.206(3) ?
  C19 O4 . 1.341(3) ?
  C20 O4 . 1.444(3) ?
  C20 H20A . 0.9800 ?
  C20 H20B . 0.9800 ?
  C20 H20C . 0.9800 ?
_cod_database_code 2012686