#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008416.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_2008416
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
L-Menthyl ester of highly estrogenic (-)-(Z)-bisdehydrodoisynolic acid
3-methyl ether
;
loop_
_publ_author_name
  'Robinson, Paul D.'
  'Hou, Yuqing'
  'Meyers, Cal Y.'
  'Adler, Stuart'
  'Banz, William J.'
  'Winters, Todd A.'
_chemical_formula_sum  'C29 H40 O3'
_chemical_formula_weight  436.61
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  10.9185(11)
_cell_length_b  28.281(4)
_cell_length_c  8.6380(7)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2667.3(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.087
_diffrn_ambient_temperature  296
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 0.1462(4) 0.55699(15) 0.4523(4) 0.1098(11) Uani d . 1 . . O
  O2 -0.0292(3) 0.19288(12) 0.2321(4) 0.1033(12) Uani d . 1 . . O
  O3 0.1448(3) 0.18495(12) 0.3667(3) 0.0810(9) Uani d . 1 . . O
  C1 0.0204(4) 0.4451(2) 0.3338(6) 0.0905(15) Uani d . 1 . . C
  C2 0.0421(5) 0.4920(2) 0.3498(6) 0.0926(15) Uani d . 1 . . C
  C3 0.1333(5) 0.5089(2) 0.4508(6) 0.0885(14) Uani d . 1 . . C
  C4 0.2002(4) 0.4777(2) 0.5355(6) 0.0866(14) Uani d . 1 . . C
  C5 0.1783(4) 0.4287(2) 0.5221(6) 0.0788(14) Uani d . 1 . . C
  C6 0.2472(4) 0.3948(2) 0.6071(6) 0.0831(14) Uani d . 1 . . C
  C7 0.2264(4) 0.3479(2) 0.5918(5) 0.0819(14) Uani d . 1 . . C
  C8 0.1363(4) 0.33015(17) 0.4892(5) 0.0717(12) Uani d . 1 . . C
  C9 0.0686(4) 0.36095(19) 0.4020(5) 0.0723(13) Uani d . 1 . . C
  C10 0.0886(4) 0.4106(2) 0.4192(5) 0.0751(13) Uani d . 1 . . C
  C11 -0.0201(4) 0.34396(18) 0.2801(5) 0.0934(15) Uani d . 1 . . C
  C12 -0.0355(4) 0.29037(18) 0.2691(5) 0.0897(15) Uani d . 1 . . C
  C13 0.0804(4) 0.26326(18) 0.3124(5) 0.0717(12) Uani d . 1 . . C
  C14 0.1159(4) 0.27725(15) 0.4786(4) 0.0722(13) Uani d . 1 . . C
  C15 0.0217(4) 0.25991(16) 0.6001(4) 0.0844(13) Uani d . 1 . . C
  C16 0.0721(5) 0.2567(2) 0.7641(5) 0.127(2) Uani d . 1 . . C
  C17 0.0562(5) 0.2103(2) 0.2980(5) 0.0790(14) Uani d . 1 . . C
  C18 0.1866(4) 0.27446(16) 0.1994(5) 0.0883(14) Uani d . 1 . . C
  C19 0.2482(5) 0.5762(2) 0.5321(7) 0.132(2) Uani d . 1 . . C
  C1' 0.0704(4) 0.06602(19) 0.5420(6) 0.0955(16) Uani d . 1 . . C
  C2' 0.0809(4) 0.11930(18) 0.5262(5) 0.0889(15) Uani d . 1 . . C
  C3' 0.1315(4) 0.13363(18) 0.3696(5) 0.0785(13) Uani d . 1 . . C
  C4' 0.2580(4) 0.11238(16) 0.3387(5) 0.0758(13) Uani d . 1 . . C
  C5' 0.2504(4) 0.05855(17) 0.3565(6) 0.0951(15) Uani d . 1 . . C
  C6' 0.1948(5) 0.04373(18) 0.5103(6) 0.1027(17) Uani d . 1 . . C
  C7' 0.0168(5) 0.0517(2) 0.6985(6) 0.135(2) Uani d . 1 . . C
  C8' 0.3113(4) 0.12841(18) 0.1830(5) 0.0888(15) Uani d . 1 . . C
  C9' 0.4418(4) 0.10941(19) 0.1623(6) 0.1107(18) Uani d . 1 . . C
  C10' 0.2320(4) 0.1154(2) 0.0435(5) 0.127(2) Uani d . 1 . . C
  H1 -0.0402 0.4351 0.2656 0.109 Uiso calc R 1 . . H
  H2 -0.0042 0.5135 0.2931 0.111 Uiso calc R 1 . . H
  H4 0.2606 0.4887 0.6024 0.104 Uiso calc R 1 . . H
  H7 0.2725 0.3267 0.6501 0.098 Uiso calc R 1 . . H
  H10a 0.2678 0.1283 -0.0489 0.190 Uiso calc R 1 . . H
  H10b 0.1512 0.1282 0.0571 0.190 Uiso calc R 1 . . H
  H10c 0.2271 0.0817 0.0346 0.190 Uiso calc R 1 . . H
  H11a 0.0070 0.3556 0.1802 0.112 Uiso calc R 1 . . H
  H11b -0.0996 0.3579 0.3009 0.112 Uiso calc R 1 . . H
  H12a -0.1015 0.2807 0.3372 0.108 Uiso calc R 1 . . H
  H12b -0.0587 0.2821 0.1641 0.108 Uiso calc R 1 . . H
  H14 0.1941 0.2618 0.5020 0.087 Uiso calc R 1 . . H
  H15a -0.0478 0.2813 0.5999 0.101 Uiso calc R 1 . . H
  H15b -0.0078 0.2289 0.5694 0.101 Uiso calc R 1 . . H
  H16a 0.1413 0.2358 0.7656 0.190 Uiso calc R 1 . . H
  H16b 0.0097 0.2448 0.8320 0.190 Uiso calc R 1 . . H
  H16c 0.0969 0.2876 0.7981 0.190 Uiso calc R 1 . . H
  H18a 0.2584 0.2573 0.2302 0.132 Uiso calc R 1 . . H
  H18b 0.2036 0.3078 0.2016 0.132 Uiso calc R 1 . . H
  H18c 0.1636 0.2653 0.0964 0.132 Uiso calc R 1 . . H
  H19a 0.2434 0.5679 0.6397 0.198 Uiso calc R 1 . . H
  H19b 0.2479 0.6100 0.5218 0.198 Uiso calc R 1 . . H
  H19c 0.3225 0.5638 0.4889 0.198 Uiso calc R 1 . . H
  H1' 0.0139 0.0549 0.4616 0.115 Uiso calc R 1 . . H
  H2'a 0.0007 0.1334 0.5402 0.107 Uiso calc R 1 . . H
  H2'b 0.1342 0.1313 0.6070 0.107 Uiso calc R 1 . . H
  H3' 0.0747 0.1237 0.2880 0.094 Uiso calc R 1 . . H
  H4' 0.3130 0.1240 0.4199 0.091 Uiso calc R 1 . . H
  H5'a 0.2012 0.0457 0.2730 0.114 Uiso calc R 1 . . H
  H5'b 0.3320 0.0453 0.3479 0.114 Uiso calc R 1 . . H
  H6 0.3078 0.4051 0.6747 0.100 Uiso calc R 1 . . H
  H6'a 0.2506 0.0524 0.5930 0.123 Uiso calc R 1 . . H
  H6'b 0.1862 0.0096 0.5116 0.123 Uiso calc R 1 . . H
  H7'a 0.0718 0.0611 0.7797 0.203 Uiso calc R 1 . . H
  H7'b 0.0057 0.0180 0.7014 0.203 Uiso calc R 1 . . H
  H7'c -0.0608 0.0670 0.7130 0.203 Uiso calc R 1 . . H
  H8' 0.3169 0.1630 0.1860 0.107 Uiso calc R 1 . . H
  H9'a 0.4389 0.0758 0.1462 0.166 Uiso calc R 1 . . H
  H9'b 0.4890 0.1162 0.2533 0.166 Uiso calc R 1 . . H
  H9'c 0.4791 0.1243 0.0742 0.166 Uiso calc R 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 0.108(3) 0.111(3) 0.110(3) -0.008(2) 0.011(3) 0.018(2)
  O2 0.075(2) 0.135(3) 0.099(3) -0.021(2) -0.019(2) 0.012(2)
  O3 0.0692(19) 0.098(3) 0.076(2) -0.0056(18) -0.0079(18) -0.0040(19)
  C1 0.070(3) 0.115(4) 0.087(4) 0.008(3) -0.001(3) 0.009(4)
  C2 0.078(4) 0.115(5) 0.085(4) 0.016(3) -0.003(3) 0.023(3)
  C3 0.070(3) 0.111(5) 0.084(4) 0.003(4) 0.015(3) 0.021(4)
  C4 0.066(3) 0.118(5) 0.076(4) -0.005(3) 0.003(3) 0.003(3)
  C5 0.048(3) 0.119(5) 0.069(3) 0.003(3) -0.002(3) 0.002(3)
  C6 0.047(2) 0.129(4) 0.073(3) 0.003(3) -0.016(3) -0.002(3)
  C7 0.063(3) 0.116(4) 0.066(3) 0.009(3) -0.012(3) 0.007(3)
  C8 0.054(2) 0.106(4) 0.055(3) 0.005(3) -0.006(3) 0.005(3)
  C9 0.052(2) 0.105(4) 0.059(3) 0.011(3) -0.008(3) 0.009(3)
  C10 0.055(3) 0.108(4) 0.062(3) 0.018(3) -0.001(3) 0.015(3)
  C11 0.077(3) 0.130(5) 0.074(3) 0.014(3) -0.019(3) 0.001(3)
  C12 0.074(3) 0.123(4) 0.072(3) 0.000(3) -0.013(3) 0.008(3)
  C13 0.055(3) 0.106(4) 0.054(3) 0.002(3) -0.002(2) 0.001(3)
  C14 0.056(3) 0.113(4) 0.047(3) 0.010(3) -0.008(2) 0.008(3)
  C15 0.081(3) 0.114(4) 0.059(3) 0.010(3) 0.005(3) 0.005(3)
  C16 0.138(5) 0.187(6) 0.055(3) 0.006(5) -0.005(3) 0.026(4)
  C17 0.064(3) 0.119(5) 0.054(3) 0.002(4) 0.004(3) 0.005(3)
  C18 0.083(3) 0.122(4) 0.060(3) -0.005(3) 0.004(3) 0.005(3)
  C19 0.122(5) 0.123(5) 0.150(6) -0.035(4) 0.007(5) 0.003(4)
  C1' 0.082(4) 0.120(4) 0.085(4) -0.022(3) 0.004(3) 0.010(3)
  C2' 0.070(3) 0.132(4) 0.065(3) -0.006(3) 0.010(3) -0.006(3)
  C3' 0.061(3) 0.112(4) 0.063(3) -0.012(3) 0.005(3) -0.009(3)
  C4' 0.060(3) 0.101(4) 0.066(3) -0.009(3) 0.005(3) -0.013(3)
  C5' 0.074(3) 0.108(4) 0.102(4) -0.007(3) 0.010(3) -0.012(3)
  C6' 0.091(4) 0.108(4) 0.109(4) -0.005(3) 0.006(4) 0.014(4)
  C7' 0.123(5) 0.177(6) 0.105(5) -0.014(4) 0.024(4) 0.035(4)
  C8' 0.073(3) 0.126(4) 0.066(3) -0.010(3) 0.007(3) -0.009(3)
  C9' 0.071(3) 0.169(5) 0.093(4) -0.010(4) 0.020(3) -0.007(4)
  C10' 0.098(4) 0.221(6) 0.061(3) -0.015(4) 0.003(3) -0.014(4)
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 C3 . 1.368(5) no
  O1 C19 . 1.419(6) no
  O2 C17 . 1.199(5) no
  O3 C17 . 1.343(5) no
  O3 C3' . 1.459(5) no
  C1 C2 . 1.354(6) no
  C1 C10 . 1.433(6) no
  C1' C2' . 1.517(6) no
  C1' C6' . 1.523(6) no
  C1' C7' . 1.528(6) no
  C2 C3 . 1.406(6) no
  C2' C3' . 1.517(5) no
  C3 C4 . 1.359(6) no
  C3' C4' . 1.530(6) no
  C4 C5 . 1.412(6) no
  C4' C5' . 1.533(6) no
  C4' C8' . 1.534(6) no
  C5 C10 . 1.418(6) no
  C5 C6 . 1.422(6) no
  C5' C6' . 1.519(6) no
  C6 C7 . 1.352(6) no
  C7 C8 . 1.415(5) no
  C8 C9 . 1.369(5) no
  C8 C14 . 1.515(5) no
  C8' C10' . 1.529(6) no
  C8' C9' . 1.533(5) no
  C9 C10 . 1.429(6) no
  C9 C11 . 1.509(5) no
  C11 C12 . 1.528(5) no
  C12 C13 . 1.526(5) no
  C13 C17 . 1.525(6) no
  C13 C14 . 1.539(5) no
  C13 C18 . 1.548(5) no
  C14 C15 . 1.549(5) no
  C15 C16 . 1.522(6) no
  C1 H1 . 0.9300 no
  C1' H1' . 0.9800 no
  C2' H2'a . 0.9700 no
  C2' H2'b . 0.9700 no
  C2 H2 . 0.9300 no
  C3' H3' . 0.9800 no
  C4 H4 . 0.9300 no
  C4' H4' . 0.9800 no
  C5' H5'a . 0.9700 no
  C5' H5'b . 0.9700 no
  C6 H6 . 0.9300 no
  C6' H6'a . 0.9700 no
  C6' H6'b . 0.9700 no
  C7' H7'a . 0.9600 no
  C7' H7'b . 0.9600 no
  C7' H7'c . 0.9600 no
  C7 H7 . 0.9300 no
  C9' H9'a . 0.9600 no
  C9' H9'b . 0.9600 no
  C9' H9'c . 0.9600 no
  C10' H10a . 0.9600 no
  C10' H10b . 0.9600 no
  C10' H10c . 0.9600 no
  C11 H11a . 0.9700 no
  C11 H11b . 0.9700 no
  C8' H8' . 0.9800 no
  C12 H12a . 0.9700 no
  C12 H12b . 0.9700 no
  C14 H14 . 0.9800 no
  C15 H15a . 0.9700 no
  C15 H15b . 0.9700 no
  C16 H16a . 0.9600 no
  C16 H16b . 0.9600 no
  C16 H16c . 0.9600 no
  C18 H18a . 0.9600 no
  C18 H18b . 0.9600 no
  C18 H18c . 0.9600 no
  C19 H19a . 0.9600 no
  C19 H19b . 0.9600 no
  C19 H19c . 0.9600 no
_cod_database_code 2008416