#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200186.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_2200186
_publ_section_title
;
Cyclodec-2-ynyl
(1S,1'R)-(-)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
;
loop_
_publ_author_name
  'Zelder, Claudia'
  'Sch\"urmann, Markus'
  'Preut, Hans'
  'Krause, Norbert'
_chemical_formula_moiety  'C20 H28 O4'
_chemical_formula_sum  'C20 H28 O4'
_chemical_formula_iupac  'C20 H28 O4'
_chemical_formula_weight  332.42
_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, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  6.5640(3)
_cell_length_b  9.7316(5)
_cell_length_c  28.4686(14)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1818.52(15)
_cell_formula_units_Z  4
_cell_measurement_temperature  291.0(10)
_exptl_crystal_density_diffrn  1.214
_diffrn_ambient_temperature  291.0(10)
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  .8919(3)  .69183(19)  .90156(6)  .0553(6) Uani d . 1 . . O
  O2  .9064(3)  .9255(2)  .94932(6)  .0571(6) Uani d . 1 . . O
  O3  .5836(4)  .6372(2)  .93045(8)  .0819(8) Uani d . 1 . . O
  O4 1.0102(4) 1.1446(2)  .95491(9)  .0827(8) Uani d . 1 . . O
  C1  .7061(5)  .8631(3)  .94319(10)  .0470(8) Uani d . 1 . . C
  C3  .8734(6) 1.0658(3)  .94989(10)  .0555(8) Uani d . 1 . . C
  C4  .6468(4) 1.0881(3)  .94386(10)  .0489(8) Uani d . 1 . . C
  C5  .5580(5) 1.0389(3)  .99100(9)  .0638(10) Uani d . 1 . . C
  H5A  .6270 1.0820 1.0173  .077 Uiso calc R 1 . . H
  H5B  .4133 1.0585  .9930  .077 Uiso calc R 1 . . H
  C6  .5975(6)  .8831(3)  .99009(10)  .0681(10) Uani d . 1 . . C
  H6A  .6832  .8550 1.0161  .082 Uiso calc R 1 . . H
  H6B  .4709  .8318  .9912  .082 Uiso calc R 1 . . H
  C7  .6009(5)  .9658(3)  .91015(9)  .0498(8) Uani d . 1 . . C
  C8  .7212(6)  .7180(3)  .92567(10)  .0549(9) Uani d . 1 . . C
  C9  .7080(6)  .9766(3)  .86229(9)  .0720(10) Uani d . 1 . . C
  H9A  .8496  .9972  .8670  .108 Uiso calc R 1 . . H
  H9B  .6461 1.0485  .8441  .108 Uiso calc R 1 . . H
  H9C  .6953  .8909  .8458  .108 Uiso calc R 1 . . H
  C10  .3750(5)  .9368(4)  .90170(12)  .0853(11) Uani d . 1 . . C
  H10A  .3597  .8469  .8883  .128 Uiso calc R 1 . . H
  H10B  .3206 1.0042  .8805  .128 Uiso calc R 1 . . H
  H10C  .3030  .9410  .9310  .128 Uiso calc R 1 . . H
  C11  .5898(6) 1.2321(3)  .93084(11)  .0765(11) Uani d . 1 . . C
  H11A  .6429 1.2532  .9003  .115 Uiso calc R 1 . . H
  H11B  .6458 1.2948  .9534  .115 Uiso calc R 1 . . H
  H11C  .4441 1.2407  .9305  .115 Uiso calc R 1 . . H
  C1'  .6888(5)  .5408(3)  .80101(12)  .0573(9) Uani d . 1 . . C
  C2'  .7664(5)  .5567(3)  .83747(12)  .0554(9) Uani d . 1 . . C
  C3'  .8969(5)  .5565(3)  .87930(10)  .0551(8) Uani d . 1 . . C
  H3'  .8488  .4868  .9015  .066 Uiso calc R 1 . . H
  C4' 1.1170(5)  .5284(3)  .86658(10)  .0570(9) Uani d . 1 . . C
  H4'1 1.2032  .5573  .8924  .068 Uiso calc R 1 . . H
  H4'2 1.1529  .5834  .8394  .068 Uiso calc R 1 . . H
  C5' 1.1607(5)  .3772(3)  .85570(11)  .0710(10) Uani d . 1 . . C
  H5'1 1.1459  .3259  .8847  .085 Uiso calc R 1 . . H
  H5'2 1.3024  .3701  .8463  .085 Uiso calc R 1 . . H
  C6' 1.0314(6)  .3049(3)  .81791(11)  .0682(10) Uani d . 1 . . C
  H6'1 1.0715  .2091  .8167  .082 Uiso calc R 1 . . H
  H6'2  .8899  .3079  .8277  .082 Uiso calc R 1 . . H
  C7' 1.0461(5)  .3640(3)  .76858(11)  .0732(10) Uani d . 1 . . C
  H7'1 1.1792  .3415  .7560  .088 Uiso calc R 1 . . H
  H7'2 1.0378  .4633  .7708  .088 Uiso calc R 1 . . H
  C8'  .8845(6)  .3149(4)  .73377(11)  .0819(12) Uani d . 1 . . C
  H8'1  .9148  .3552  .7034  .098 Uiso calc R 1 . . H
  H8'2  .8981  .2161  .7305  .098 Uiso calc R 1 . . H
  C9'  .6627(6)  .3466(3)  .74556(11)  .0752(11) Uani d . 1 . . C
  H9'1  .5783  .3148  .7198  .090 Uiso calc R 1 . . H
  H9'2  .6251  .2941  .7732  .090 Uiso calc R 1 . . H
  C10'  .6137(6)  .4972(3)  .75466(10)  .0677(10) Uani d . 1 . . C
  H0'1  .6760  .5534  .7305  .081 Uiso calc R 1 . . H
  H0'2  .4674  .5108  .7532  .081 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  .0554(16)  .0531(14)  .0575(13)  .0024(12)  .0075(12)  -.0126(11)
  O2  .0459(14)  .0596(15)  .0658(13)  .0033(12)  -.0086(11)  -.0114(11)
  O3  .0750(18)  .0707(15)  .0999(18)  -.0231(15)  .0314(15)  -.0182(13)
  O4  .0612(17)  .0713(17)  .1154(19)  -.0206(14)  -.0018(14)  -.0278(14)
  C1  .044(2)  .050(2)  .0479(19)  -.0042(16)  .0048(16)  -.0057(16)
  C3  .062(3)  .050(2)  .0546(19)  .004(2)  .0041(18)  -.0129(17)
  C4  .049(2)  .049(2)  .0493(19)  .0094(17)  .0033(16)  -.0026(16)
  C5  .072(2)  .061(2)  .059(2)  .005(2)  .0183(18)  -.0115(17)
  C6  .086(3)  .068(2)  .0508(19)  .000(2)  .0192(19)  -.0038(16)
  C7  .041(2)  .062(2)  .0457(17)  -.0013(18)  -.0016(15)  -.0008(16)
  C8  .059(3)  .058(2)  .047(2)  -.003(2)  .005(2)  -.0050(17)
  C9  .089(3)  .078(2)  .0494(17)  -.005(2)  .0003(19)  .0038(17)
  C10  .055(3)  .103(3)  .098(3)  -.004(2)  -.012(2)  -.011(2)
  C11  .082(3)  .063(2)  .085(2)  .008(2)  -.004(2)  .0025(18)
  C1'  .054(2)  .052(2)  .067(2)  .0032(17)  -.0050(19)  -.0098(19)
  C2'  .053(2)  .050(2)  .063(2)  .0066(19)  .0006(19)  -.0138(18)
  C3'  .061(2)  .050(2)  .0544(18)  .0018(19)  .0028(18)  -.0090(16)
  C4'  .054(2)  .058(2)  .0585(19)  .0076(19)  -.0048(16)  -.0062(16)
  C5'  .062(3)  .079(2)  .072(2)  .019(2)  .000(2)  .005(2)
  C6'  .073(3)  .053(2)  .079(2)  .013(2)  .009(2)  -.0061(19)
  C7'  .067(3)  .082(2)  .070(2)  .002(2)  .020(2)  -.005(2)
  C8'  .083(3)  .090(3)  .073(2)  -.006(3)  .003(2)  -.028(2)
  C9'  .080(3)  .075(3)  .071(2)  -.015(2)  -.013(2)  -.0146(19)
  C10'  .070(3)  .065(2)  .068(2)  -.0047(19)  -.0167(19)  -.0018(17)
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 C8 . 1.338(4) ?
  O1 C3' . 1.462(3) ?
  O2 C3 . 1.383(3) ?
  O2 C1 . 1.459(3) ?
  O3 C8 . 1.205(4) ?
  O4 C3 . 1.189(3) ?
  C1 C8 . 1.501(4) ?
  C1 C6 . 1.526(4) ?
  C1 C7 . 1.536(4) ?
  C3 C4 . 1.512(4) ?
  C4 C11 . 1.497(4) ?
  C4 C5 . 1.540(4) ?
  C4 C7 . 1.558(4) ?
  C5 C6 . 1.539(4) ?
  C5 H5A .  .9700 ?
  C5 H5B .  .9700 ?
  C6 H6A .  .9700 ?
  C6 H6B .  .9700 ?
  C7 C10 . 1.529(4) ?
  C7 C9 . 1.537(4) ?
  C9 H9A .  .9600 ?
  C9 H9B .  .9600 ?
  C9 H9C .  .9600 ?
  C10 H10A .  .9600 ?
  C10 H10B .  .9600 ?
  C10 H10C .  .9600 ?
  C11 H11A .  .9600 ?
  C11 H11B .  .9600 ?
  C11 H11C .  .9600 ?
  C1' C2' . 1.167(4) yes
  C1' C10' . 1.471(4) yes
  C2' C3' . 1.467(4) yes
  C3' C4' . 1.514(4) ?
  C3' H3' .  .9800 ?
  C4' C5' . 1.531(4) ?
  C4' H4'1 .  .9700 ?
  C4' H4'2 .  .9700 ?
  C5' C6' . 1.540(4) ?
  C5' H5'1 .  .9700 ?
  C5' H5'2 .  .9700 ?
  C6' C7' . 1.521(4) ?
  C6' H6'1 .  .9700 ?
  C6' H6'2 .  .9700 ?
  C7' C8' . 1.528(4) ?
  C7' H7'1 .  .9700 ?
  C7' H7'2 .  .9700 ?
  C8' C9' . 1.526(5) ?
  C8' H8'1 .  .9700 ?
  C8' H8'2 .  .9700 ?
  C9' C10' . 1.523(4) ?
  C9' H9'1 .  .9700 ?
  C9' H9'2 .  .9700 ?
  C10' H0'1 .  .9700 ?
  C10' H0'2 .  .9700 ?
_cod_database_code 2200186