data_2011164
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e300
_journal_page_last  e301
_publ_section_title
;
6-Dimethoxymethyl-1-methoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acid
;
loop_
_publ_author_name
  'Niwayama, Satomi'
  'Holt, Elizabeth M.'
_chemical_formula_moiety  'C12 H16 O6'
_chemical_formula_sum  'C12 H16 O6'
_chemical_formula_weight  256.25
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  7.537(4)
_cell_length_b  13.602(8)
_cell_length_c  12.779(5)
_cell_angle_alpha  90.00
_cell_angle_beta  94.57(2)
_cell_angle_gamma  90.00
_cell_volume  1305.9(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.303
_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
  C1  .7023(3)  .72696(17)  .15677(19)  .0400(6) Uani d . 1 . . C
  C2  .6771(3)  .66163(18)  .06139(18)  .0394(6) Uani d . 1 . . C
  C3  .5121(3)  .6704(2)  .0124(2)  .0485(6) Uani d . 1 . . C
  H3A  .4460  .6347  -.0535  .050 Uiso d R 1 . . H
  C4  .4010(3)  .7463(2)  .0634(2)  .0543(7) Uani d . 1 . . C
  H4A  .2921  .7181  .0837  .080 Uiso d R 1 . . H
  H4B  .3733  .8005  .0169  .080 Uiso d R 1 . . H
  C5  .5208(3)  .77995(18)  .1608(2)  .0483(7) Uani d . 1 . . C
  H5A  .5221  .8484  .1790  .080 Uiso d R 1 . . H
  C6  .5815(3)  .70636(17)  .24505(19)  .0421(6) Uani d . 1 . . C
  H6A  .6222  .7353  .3112  .080 Uiso d R 1 . . H
  C7  .8776(3)  .78091(17)  .1753(2)  .0472(6) Uani d . 1 . . C
  C8 1.0960(4)  .8403(3)  .3052(3)  .0757(10) Uani d . 1 . . C
  H8A 1.1178  .8439  .3802  .080 Uiso d R 1 . . H
  H8B 1.1906  .8045  .2765  .080 Uiso d R 1 . . H
  H8C 1.0905  .9056  .2765  .080 Uiso d R 1 . . H
  C9  .8167(3)  .59090(18)  .03472(18)  .0406(6) Uani d . 1 . . C
  C10  .4876(3)  .60834(18)  .25657(18)  .0413(6) Uani d . 1 . . C
  H10A  .4265  .5917  .1901  .080 Uiso d R 1 . . H
  C11  .7129(5)  .5464(3)  .3835(3)  .0862(12) Uani d . 1 . . C
  H11A  .7866  .4900  .3998  .080 Uiso d R 1 . . H
  H11B  .7868  .6029  .3750  .080 Uiso d R 1 . . H
  H11C  .6381  .5580  .4396  .080 Uiso d R 1 . . H
  C12  .2272(4)  .5514(3)  .3339(3)  .0688(9) Uani d . 1 . . C
  H12A  .1464  .5683  .3854  .080 Uiso d R 1 . . H
  H12B  .1629  .5462  .2662  .080 Uiso d R 1 . . H
  H12C  .2831  .4897  .3521  .080 Uiso d R 1 . . H
  O1  .9631(3)  .81238(18)  .10620(19)  .0708(7) Uani d . 1 . . O
  O2  .9284(3)  .79096(16)  .27818(17)  .0628(6) Uani d . 1 . . O
  O3  .9586(2)  .58392(15)  .08861(15)  .0550(6) Uani d . 1 . . O
  O4  .7758(2)  .53716(16)  -.05012(15)  .0590(6) Uani d . 1 . . O
  H4C  .8645  .4866  -.0518  .050 Uiso d R 1 . . H
  O5  .6047(3)  .52982(14)  .28781(16)  .0576(6) Uani d . 1 . . O
  O6  .3600(2)  .62621(14)  .32987(15)  .0529(5) 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  .0363(12)  .0356(11)  .0497(13)  .0031(9)  .0133(10)  -.0003(9)
  C2  .0377(12)  .0417(12)  .0402(12)  .0013(10)  .0123(9)  .0031(9)
  C3  .0431(13)  .0599(15)  .0435(13)  .0041(12)  .0087(10)  .0068(11)
  C4  .0413(13)  .0602(16)  .0626(16)  .0137(12)  .0127(11)  .0164(13)
  C5  .0400(13)  .0375(12)  .0700(17)  .0049(10)  .0206(11)  -.0011(11)
  C6  .0432(13)  .0387(12)  .0460(13)  -.0001(10)  .0138(10)  -.0081(10)
  C7  .0409(13)  .0350(12)  .0673(17)  .0024(10)  .0147(11)  -.0059(11)
  C8  .0465(16)  .079(2)  .101(3)  -.0055(16)  -.0009(16)  -.031(2)
  C9  .0398(12)  .0439(12)  .0392(11)  .0002(10)  .0104(9)  -.0045(9)
  C10  .0435(12)  .0428(13)  .0389(12)  -.0020(10)  .0113(9)  -.0023(9)
  C11  .062(2)  .096(3)  .098(3)  .014(2)  -.0106(19)  .025(2)
  C12  .0543(16)  .082(2)  .071(2)  -.0231(16)  .0148(14)  .0068(17)
  O1  .0568(13)  .0771(15)  .0816(15)  -.0193(11)  .0250(11)  .0044(12)
  O2  .0467(11)  .0706(14)  .0714(13)  -.0107(10)  .0059(9)  -.0171(11)
  O3  .0470(10)  .0614(12)  .0559(11)  .0141(9)  .0000(8)  -.0175(9)
  O4  .0450(10)  .0710(13)  .0606(12)  .0110(9)  .0023(8)  -.0241(10)
  O5  .0607(12)  .0435(10)  .0706(13)  .0059(9)  .0170(9)  .0057(9)
  O6  .0454(10)  .0592(11)  .0564(11)  -.0067(8)  .0194(8)  -.0044(9)
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 . 1.508(3) yes
  C1 C7 . 1.513(4) yes
  C1 C6 . 1.531(3) yes
  C1 C5 . 1.551(3) yes
  C2 C3 . 1.353(4) yes
  C2 C9 . 1.485(3) yes
  C3 C4 . 1.509(4) yes
  C3 H3A . 1.0613 no
  C4 C5 . 1.548(4) yes
  C4 H4A .  .9600 no
  C4 H4B .  .9599 no
  C5 C6 . 1.514(4) yes
  C5 H5A .  .9601 no
  C6 C10 . 1.522(3) yes
  C6 H6A .  .9600 no
  C7 O1 . 1.212(3) yes
  C7 O2 . 1.347(3) yes
  C8 O2 . 1.448(4) yes
  C8 H8A .  .9601 no
  C8 H8B .  .9600 no
  C8 H8C .  .9601 no
  C9 O3 . 1.228(3) yes
  C9 O4 . 1.323(3) yes
  C10 O6 . 1.416(3) yes
  C10 O5 . 1.422(3) yes
  C10 H10A .  .9600 no
  C11 O5 . 1.433(4) yes
  C11 H11A .  .9600 no
  C11 H11B .  .9600 no
  C11 H11C .  .9600 no
  C12 O6 . 1.431(3) yes
  C12 H12A .  .9600 no
  C12 H12B .  .9600 no
  C12 H12C .  .9600 no
  O4 H4C .  .9600 yes