#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013214.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_2013214
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o132
_journal_page_last  o134
_publ_section_title
;
Dimethyl 4a\b-methyl-6-methoxy-9-oxo-1,2,3,4,4a,9,10,10a\b-
octahydrophenanthrene-1,1-dicarboxylate: a supramolecular framework built
from C---H...O hydrogen bonds.
;
loop_
_publ_author_name
  'Swastik Mondal'
  'Monika Mukherjee'
  'Arnab Roy'
  'Debabrata Mukherjee'
_chemical_formula_moiety  'C20 H24 O6'
_chemical_formula_sum  'C20 H24 O6'
_chemical_formula_iupac  'C20 H24 O6'
_chemical_formula_weight  360.39
_chemical_melting_point  431
_symmetry_cell_setting  'orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  9.491(4)
_cell_length_b  13.541(5)
_cell_length_c  14.051(6)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1805.8(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.326
_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
  O1 0.7636(2) 0.93442(12) 0.62722(13) 0.0630(5) Uani d . 1 . . O
  O2 0.66719(17) 0.36410(11) 0.89782(11) 0.0527(4) Uani d . 1 . . O
  O3 0.87678(17) 0.36779(11) 0.82597(13) 0.0560(4) Uani d . 1 . . O
  O4 0.92799(17) 0.58559(13) 0.72734(13) 0.0629(5) Uani d . 1 . . O
  O5 0.89428(15) 0.57374(11) 0.88402(11) 0.0489(4) Uani d . 1 . . O
  O6 0.7192(2) 0.71233(12) 1.01841(11) 0.0663(5) Uani d . 1 . . O
  C1 0.7231(2) 0.49742(14) 0.78803(13) 0.0377(4) Uani d . 1 . . C
  C2 0.6967(3) 0.46354(15) 0.68437(15) 0.0505(5) Uani d . 1 . . C
  H2A 0.7832 0.4362 0.6587 0.061 Uiso calc . 1 . . H
  H2B 0.6264 0.4116 0.6844 0.061 Uiso calc . 1 . . H
  C3 0.6474(3) 0.54649(17) 0.62057(15) 0.0540(6) Uani d . 1 . . C
  H3A 0.6275 0.5207 0.5576 0.065 Uiso calc . 1 . . H
  H3B 0.7215 0.5955 0.6147 0.065 Uiso calc . 1 . . H
  C4 0.5164(2) 0.59446(15) 0.66056(15) 0.0488(5) Uani d . 1 . . C
  H4A 0.4408 0.5463 0.6609 0.059 Uiso calc . 1 . . H
  H4B 0.4884 0.6480 0.6188 0.059 Uiso calc . 1 . . H
  C4A 0.53461(18) 0.63541(14) 0.76175(14) 0.0381(4) Uani d . 1 . . C
  C4B 0.63235(19) 0.72474(13) 0.76823(13) 0.0364(4) Uani d . 1 . . C
  C5 0.6540(2) 0.78668(15) 0.69113(14) 0.0415(4) Uani d . 1 . . C
  H5 0.6131 0.7716 0.6328 0.050 Uiso calc . 1 . . H
  C6 0.7362(2) 0.87093(15) 0.69994(17) 0.0477(5) Uani d . 1 . . C
  C7 0.7970(3) 0.89506(16) 0.78679(19) 0.0546(5) Uani d . 1 . . C
  H7 0.8521 0.9516 0.7927 0.065 Uiso calc . 1 . . H
  C8 0.7752(2) 0.83510(16) 0.86315(16) 0.0514(5) Uani d . 1 . . C
  H8 0.8156 0.8513 0.9214 0.062 Uiso calc . 1 . . H
  C8A 0.6933(2) 0.74956(14) 0.85579(14) 0.0409(4) Uani d . 1 . . C
  C9 0.6768(2) 0.68642(15) 0.94085(14) 0.0458(5) Uani d . 1 . . C
  C10 0.6035(2) 0.58838(15) 0.92941(14) 0.0435(4) Uani d . 1 . . C
  H10A 0.5097 0.5937 0.9564 0.052 Uiso calc . 1 . . H
  H10B 0.6544 0.5393 0.9661 0.052 Uiso calc . 1 . . H
  C10A 0.5902(2) 0.55137(14) 0.82712(13) 0.0362(4) Uani d . 1 . . C
  C11 0.3881(2) 0.66906(18) 0.79588(19) 0.0541(5) Uani d . 1 . . C
  H11A 0.3971 0.7031 0.8555 0.081 Uiso calc R 1 . . H
  H11B 0.3284 0.6124 0.8039 0.081 Uiso calc R 1 . . H
  H11C 0.3474 0.7126 0.7495 0.081 Uiso calc R 1 . . H
  C12 0.7158(4) 0.9088(2) 0.53487(19) 0.0725(8) Uani d . 1 . . C
  H12A 0.7545 0.8460 0.5170 0.109 Uiso calc R 1 . . H
  H12B 0.7457 0.9582 0.4902 0.109 Uiso calc R 1 . . H
  H12C 0.6148 0.9049 0.5349 0.109 Uiso calc R 1 . . H
  C13 0.7491(2) 0.40323(14) 0.84554(14) 0.0402(4) Uani d . 1 . . C
  C14 0.9186(3) 0.27936(18) 0.8753(2) 0.0665(7) Uani d . 1 . . C
  H14A 0.9128 0.2901 0.9427 0.100 Uiso calc R 1 . . H
  H14B 1.0137 0.2629 0.8583 0.100 Uiso calc R 1 . . H
  H14C 0.8571 0.2261 0.8577 0.100 Uiso calc R 1 . . H
  C15 0.8599(2) 0.55814(14) 0.79327(16) 0.0424(5) Uani d . 1 . . C
  C16 1.0188(2) 0.63208(18) 0.9029(2) 0.0679(7) Uani d . 1 . . C
  H16A 1.0991 0.6011 0.8741 0.102 Uiso calc R 1 . . H
  H16B 1.0331 0.6368 0.9704 0.102 Uiso calc R 1 . . H
  H16C 1.0067 0.6970 0.8768 0.102 Uiso calc R 1 . . H
  H1 0.5111 0.5011 0.8268 0.050 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
  O1 0.0758(11) 0.0457(8) 0.0676(10) -0.0134(8) 0.0124(9) 0.0061(8)
  O2 0.0542(9) 0.0442(7) 0.0598(9) -0.0038(7) 0.0077(7) 0.0101(7)
  O3 0.0532(9) 0.0384(7) 0.0765(10) 0.0099(7) 0.0132(8) 0.0069(8)
  O4 0.0553(9) 0.0580(9) 0.0755(11) -0.0080(8) 0.0209(8) 0.0100(9)
  O5 0.0397(7) 0.0449(8) 0.0619(9) -0.0033(7) -0.0028(7) -0.0077(7)
  O6 0.0979(13) 0.0566(9) 0.0445(8) 0.0124(10) -0.0164(9) -0.0134(7)
  C1 0.0425(10) 0.0316(8) 0.0390(9) -0.0003(8) 0.0054(8) -0.0057(7)
  C2 0.0690(13) 0.0399(10) 0.0428(11) -0.0024(10) 0.0058(10) -0.0096(9)
  C3 0.0780(15) 0.0490(11) 0.0352(9) -0.0099(12) -0.0001(10) -0.0050(9)
  C4 0.0565(12) 0.0445(10) 0.0453(10) -0.0141(10) -0.0129(9) 0.0031(9)
  C4A 0.0343(9) 0.0378(9) 0.0421(9) -0.0026(8) -0.0018(7) 0.0037(8)
  C4B 0.0330(8) 0.0338(8) 0.0423(9) 0.0035(7) 0.0007(7) -0.0035(8)
  C5 0.0409(9) 0.0384(9) 0.0451(10) 0.0003(8) 0.0022(8) -0.0022(8)
  C6 0.0449(11) 0.0348(10) 0.0633(12) -0.0003(8) 0.0096(10) -0.0006(9)
  C7 0.0508(11) 0.0368(10) 0.0760(15) -0.0055(9) -0.0033(11) -0.0100(10)
  C8 0.0541(11) 0.0410(10) 0.0590(12) 0.0034(10) -0.0106(10) -0.0156(9)
  C8A 0.0416(9) 0.0354(9) 0.0456(10) 0.0071(8) -0.0017(8) -0.0088(8)
  C9 0.0541(11) 0.0454(10) 0.0380(9) 0.0150(9) -0.0018(9) -0.0099(9)
  C10 0.0479(10) 0.0449(10) 0.0376(9) 0.0097(9) 0.0063(8) -0.0007(9)
  C10A 0.0365(9) 0.0361(9) 0.0358(9) -0.0013(7) 0.0019(7) 0.0006(7)
  C11 0.0369(10) 0.0529(12) 0.0725(14) 0.0020(9) -0.0005(10) 0.0110(11)
  C12 0.0918(19) 0.0611(15) 0.0644(15) -0.0108(15) 0.0189(14) 0.0125(13)
  C13 0.0454(10) 0.0329(9) 0.0424(10) -0.0017(8) 0.0017(9) -0.0064(8)
  C14 0.0644(14) 0.0438(12) 0.0912(18) 0.0111(11) -0.0002(15) 0.0080(13)
  C15 0.0412(10) 0.0309(9) 0.0551(11) 0.0044(8) 0.0086(9) -0.0022(8)
  C16 0.0444(11) 0.0521(12) 0.107(2) -0.0047(11) -0.0150(13) -0.0121(14)
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
  O1 C6 . 1.361(3) n
  O1 C12 . 1.418(3) n
  O2 C13 . 1.194(2) y
  O3 C13 . 1.332(3) n
  O3 C14 . 1.439(3) n
  O4 C15 . 1.189(3) y
  O5 C15 . 1.333(3) n
  O5 C16 . 1.446(3) n
  O6 C9 . 1.213(3) y
  C1 C13 . 1.530(3) n
  C1 C15 . 1.538(3) n
  C1 C2 . 1.547(3) y
  C1 C10A . 1.558(3) y
  C2 C3 . 1.511(3) y
  C2 H2A . 0.9700 n
  C2 H2B . 0.9700 n
  C3 C4 . 1.511(4) y
  C3 H3A . 0.9700 n
  C3 H3B . 0.9700 n
  C4 C4A . 1.536(3) y
  C4 H4A . 0.9700 n
  C4 H4B . 0.9700 n
  C4A C4B . 1.527(3) y
  C4A C11 . 1.540(3) n
  C4A C10A . 1.555(3) y
  C4B C5 . 1.386(3) n
  C4B C8A . 1.401(3) n
  C5 C6 . 1.387(3) n
  C5 H5 . 0.9300 n
  C6 C7 . 1.389(3) n
  C7 C8 . 1.361(3) n
  C7 H7 . 0.9300 n
  C8 C8A . 1.399(3) n
  C8 H8 . 0.9300 n
  C8A C9 . 1.478(3) n
  C9 C10 . 1.508(3) y
  C10 C10A . 1.527(3) y
  C10 H10A . 0.9700 n
  C10 H10B . 0.9700 n
  C10A H1 . 1.0132 n
  C11 H11A . 0.9600 n
  C11 H11B . 0.9600 n
  C11 H11C . 0.9600 n
  C12 H12A . 0.9600 n
  C12 H12B . 0.9600 n
  C12 H12C . 0.9600 n
  C14 H14A . 0.9600 n
  C14 H14B . 0.9600 n
  C14 H14C . 0.9600 n
  C16 H16A . 0.9600 n
  C16 H16B . 0.9600 n
  C16 H16C . 0.9600 n