data_2012871
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o491
_journal_page_last  o493
_publ_section_title
;
(+-)-2,3,4,4a,5,6,7,8-Octahydro-2-oxonaphthalene-1-acetic acid:
hydrogen-bonding pattern of the monohydrate of an unsaturated bicyclic
\g-keto acid
;
loop_
_publ_author_name
  'Lalancette, Roger A.'
  'Brunskill, Andrew P. J.'
  'Thompson, Hugh W.'
_chemical_formula_moiety  'C12 H16 O3, H2 O'
_chemical_formula_sum  'C12 H18 O4'
_chemical_formula_iupac  'C12 H16 O3, H2 O'
_chemical_formula_weight  226.26
_chemical_melting_point  368
_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  15.153(6)
_cell_length_b  9.386(3)
_cell_length_c  17.122(6)
_cell_angle_alpha  90.00
_cell_angle_beta  93.629(14)
_cell_angle_gamma  90.00
_cell_volume  2430.2(15)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.237
_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 0.26215(15) 0.9816(2) 0.37815(13) 0.0713(7) Uani d . 1 . . O
  O2 0.03598(13) 0.9225(2) 0.29939(11) 0.0602(6) Uani d . 1 . . O
  O3 -0.00080(15) 1.0538(2) 0.40079(12) 0.0598(6) Uani d . 1 . . O
  O4 -0.10169(15) 1.2220(2) 0.30984(13) 0.0619(6) Uani d . 1 . . O
  O1' 0.76558(16) 1.1173(2) 0.87722(14) 0.0761(7) Uani d . 1 . . O
  O2' 0.53650(13) 1.0622(2) 0.79772(11) 0.0589(6) Uani d . 1 . . O
  O3' 0.49506(14) 1.1832(2) 0.90148(12) 0.0577(6) Uani d . 1 . . O
  O4' 0.39593(15) 1.3572(2) 0.81181(13) 0.0606(6) Uani d . 1 . . O
  C1 0.17217(17) 0.7789(3) 0.39256(14) 0.0405(7) Uani d . 1 . . C
  C2 0.25204(19) 0.8522(3) 0.36719(16) 0.0491(8) Uani d . 1 . . C
  C3 0.3156(2) 0.7674(3) 0.3217(2) 0.0658(9) Uani d . 1 . . C
  C4 0.32025(19) 0.6149(4) 0.3469(2) 0.0647(9) Uani d . 1 . . C
  C4A 0.22998(18) 0.5433(3) 0.34476(17) 0.0497(8) Uani d . 1 . . C
  C5 0.2357(2) 0.4001(3) 0.38760(19) 0.0671(9) Uani d . 1 . . C
  C6 0.1472(2) 0.3253(3) 0.3924(2) 0.0713(10) Uani d . 1 . . C
  C7 0.0815(2) 0.4229(3) 0.4297(2) 0.0695(10) Uani d . 1 . . C
  C8 0.07255(19) 0.5638(3) 0.38615(18) 0.0551(8) Uani d . 1 . . C
  C8A 0.15972(17) 0.6384(3) 0.37723(15) 0.0420(7) Uani d . 1 . . C
  C9 0.10520(18) 0.8751(3) 0.42767(15) 0.0470(7) Uani d . 1 . . C
  C10 0.04437(17) 0.9512(3) 0.36851(17) 0.0413(7) Uani d . 1 . . C
  C1' 0.67417(17) 0.9178(3) 0.89103(14) 0.0398(7) Uani d . 1 . . C
  C2' 0.75437(18) 0.9886(3) 0.86581(16) 0.0476(7) Uani d . 1 . . C
  C3' 0.81756(19) 0.9020(3) 0.82110(19) 0.0600(9) Uani d . 1 . . C
  C4' 0.82305(18) 0.7501(3) 0.85118(18) 0.0581(8) Uani d . 1 . . C
  C4'A 0.73266(18) 0.6793(3) 0.84857(17) 0.0494(8) Uani d . 1 . . C
  C5' 0.7370(2) 0.5382(3) 0.8940(2) 0.0738(10) Uani d . 1 . . C
  C6' 0.6485(3) 0.4644(4) 0.8966(2) 0.0901(13) Uani d . 1 . . C
  C7' 0.5815(3) 0.5629(4) 0.9315(2) 0.0825(12) Uani d . 1 . . C
  C8' 0.5736(2) 0.7027(3) 0.88656(19) 0.0628(9) Uani d . 1 . . C
  C8'A 0.66143(17) 0.7765(3) 0.87760(15) 0.0430(7) Uani d . 1 . . C
  C9' 0.60735(18) 1.0151(3) 0.92552(15) 0.0485(7) Uani d . 1 . . C
  C10' 0.54332(17) 1.0873(3) 0.86724(16) 0.0409(7) Uani d . 1 . . C
  H3 -0.029(2) 1.095(4) 0.3671(19) 0.080 Uiso d . 1 . . H
  H4A -0.141(2) 1.271(4) 0.3316(19) 0.080 Uiso d . 1 . . H
  H4B -0.083(2) 1.277(4) 0.2745(19) 0.080 Uiso d . 1 . . H
  H3' 0.459(2) 1.231(4) 0.8688(18) 0.080 Uiso d . 1 . . H
  H4'A 0.356(2) 1.412(4) 0.8335(19) 0.080 Uiso d . 1 . . H
  H4'B 0.416(2) 1.411(4) 0.7806(19) 0.080 Uiso d . 1 . . H
  H3A 0.2972 0.7719 0.2665 0.079 Uiso calc R 1 . . H
  H3B 0.3740 0.8096 0.3288 0.079 Uiso calc R 1 . . H
  H4C 0.3472 0.6099 0.3998 0.078 Uiso calc R 1 . . H
  H4D 0.3579 0.5632 0.3130 0.078 Uiso calc R 1 . . H
  H4AA 0.2120 0.5240 0.2898 0.060 Uiso calc R 1 . . H
  H5A 0.2752 0.3379 0.3610 0.081 Uiso calc R 1 . . H
  H5B 0.2613 0.4155 0.4403 0.081 Uiso calc R 1 . . H
  H6A 0.1551 0.2390 0.4233 0.086 Uiso calc R 1 . . H
  H6B 0.1242 0.2986 0.3403 0.086 Uiso calc R 1 . . H
  H7A 0.0243 0.3765 0.4290 0.083 Uiso calc R 1 . . H
  H7B 0.1012 0.4404 0.4838 0.083 Uiso calc R 1 . . H
  H8A 0.0443 0.5468 0.3346 0.066 Uiso calc R 1 . . H
  H8B 0.0343 0.6263 0.4140 0.066 Uiso calc R 1 . . H
  H9A 0.0697 0.8185 0.4613 0.056 Uiso calc R 1 . . H
  H9B 0.1365 0.9456 0.4602 0.056 Uiso calc R 1 . . H
  H3'A 0.8758 0.9452 0.8262 0.072 Uiso calc R 1 . . H
  H3'B 0.7980 0.9015 0.7660 0.072 Uiso calc R 1 . . H
  H4'C 0.8484 0.7502 0.9047 0.070 Uiso calc R 1 . . H
  H4'D 0.8619 0.6955 0.8196 0.070 Uiso calc R 1 . . H
  H4'E 0.7161 0.6567 0.7937 0.059 Uiso calc R 1 . . H
  H5'A 0.7779 0.4747 0.8700 0.089 Uiso calc R 1 . . H
  H5'B 0.7601 0.5566 0.9471 0.089 Uiso calc R 1 . . H
  H6'A 0.6551 0.3786 0.9280 0.108 Uiso calc R 1 . . H
  H6'B 0.6273 0.4370 0.8441 0.108 Uiso calc R 1 . . H
  H7'A 0.5242 0.5164 0.9299 0.099 Uiso calc R 1 . . H
  H7'B 0.5997 0.5821 0.9858 0.099 Uiso calc R 1 . . H
  H8'A 0.5459 0.6842 0.8350 0.075 Uiso calc R 1 . . H
  H8'B 0.5352 0.7664 0.9134 0.075 Uiso calc R 1 . . H
  H9'A 0.5737 0.9600 0.9612 0.058 Uiso calc R 1 . . H
  H9'B 0.6391 1.0881 0.9560 0.058 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 0.0737(16) 0.0518(14) 0.0901(17) -0.0175(12) 0.0172(13) -0.0058(13)
  O2 0.0639(14) 0.0685(15) 0.0480(13) 0.0183(12) 0.0016(10) -0.0083(11)
  O3 0.0682(15) 0.0556(14) 0.0561(14) 0.0205(12) 0.0093(11) -0.0036(11)
  O4 0.0658(15) 0.0541(15) 0.0670(15) 0.0148(12) 0.0144(11) 0.0120(11)
  O1' 0.0830(17) 0.0484(14) 0.0987(18) -0.0128(13) 0.0215(14) -0.0007(13)
  O2' 0.0598(13) 0.0687(14) 0.0479(13) 0.0208(11) 0.0018(10) -0.0040(11)
  O3' 0.0587(14) 0.0562(14) 0.0582(13) 0.0220(11) 0.0050(10) -0.0045(11)
  O4' 0.0624(15) 0.0547(15) 0.0659(15) 0.0148(12) 0.0143(11) 0.0099(11)
  C1 0.0386(16) 0.0455(17) 0.0375(14) 0.0031(14) 0.0019(12) 0.0028(13)
  C2 0.0409(17) 0.050(2) 0.0553(18) -0.0051(15) -0.0023(14) 0.0049(16)
  C3 0.0452(18) 0.068(2) 0.086(2) 0.0032(17) 0.0205(17) 0.014(2)
  C4 0.0444(18) 0.072(2) 0.078(2) 0.0119(17) 0.0126(16) 0.0056(19)
  C4A 0.0488(17) 0.0521(19) 0.0487(17) 0.0100(15) 0.0058(14) -0.0024(14)
  C5 0.076(2) 0.053(2) 0.073(2) 0.0191(19) 0.0089(18) 0.0006(18)
  C6 0.090(3) 0.047(2) 0.078(2) -0.006(2) 0.010(2) 0.0002(18)
  C7 0.075(2) 0.058(2) 0.078(2) -0.0167(19) 0.0191(19) 0.0005(19)
  C8 0.0447(17) 0.054(2) 0.067(2) -0.0030(15) 0.0066(15) -0.0002(16)
  C8A 0.0391(16) 0.0427(17) 0.0440(15) 0.0031(14) 0.0016(12) 0.0051(13)
  C9 0.0486(17) 0.0454(17) 0.0475(16) -0.0001(14) 0.0074(14) -0.0015(14)
  C10 0.0365(15) 0.0388(16) 0.0494(17) -0.0012(14) 0.0098(13) -0.0036(14)
  C1' 0.0382(15) 0.0421(17) 0.0390(15) 0.0072(13) 0.0010(12) 0.0045(13)
  C2' 0.0450(17) 0.0472(19) 0.0504(17) 0.0015(15) 0.0002(14) 0.0062(15)
  C3' 0.0387(17) 0.066(2) 0.077(2) -0.0031(16) 0.0132(15) 0.0034(19)
  C4' 0.0417(17) 0.063(2) 0.071(2) 0.0118(16) 0.0089(15) 0.0019(18)
  C4'A 0.0520(18) 0.0456(18) 0.0509(17) 0.0063(15) 0.0053(14) -0.0016(15)
  C5' 0.087(3) 0.047(2) 0.088(3) 0.0116(19) 0.008(2) 0.0102(18)
  C6' 0.119(3) 0.051(2) 0.103(3) -0.016(2) 0.028(3) 0.010(2)
  C7' 0.089(3) 0.083(3) 0.077(2) -0.039(2) 0.020(2) 0.004(2)
  C8' 0.0500(19) 0.071(2) 0.068(2) -0.0134(17) 0.0115(16) -0.0073(19)
  C8'A 0.0376(15) 0.0500(18) 0.0413(15) 0.0005(14) 0.0016(12) 0.0030(13)
  C9' 0.0495(17) 0.0520(18) 0.0444(16) 0.0070(15) 0.0053(14) -0.0026(15)
  C10' 0.0360(15) 0.0408(16) 0.0470(17) 0.0002(13) 0.0107(13) 0.0005(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 C2 . 1.237(3) ?
  O2 C10 . 1.213(3) Y
  O3 C10 . 1.322(3) Y
  O1' C2' . 1.234(3) ?
  O2' C10' . 1.211(3) Y
  O3' C10' . 1.320(3) Y
  C1 C8A . 1.355(4) ?
  C1 C2 . 1.481(4) ?
  C1 C9 . 1.511(4) ?
  C2 C3 . 1.503(4) ?
  C3 C4 . 1.495(4) ?
  C4 C4A . 1.522(4) ?
  C4A C8A . 1.521(4) ?
  C4A C5 . 1.532(4) ?
  C5 C6 . 1.520(4) ?
  C6 C7 . 1.522(4) ?
  C7 C8 . 1.520(4) ?
  C8 C8A . 1.511(4) ?
  C9 C10 . 1.506(4) ?
  C1' C8'A . 1.358(4) ?
  C1' C2' . 1.473(4) ?
  C1' C9' . 1.511(4) ?
  C2' C3' . 1.502(4) ?
  C3' C4' . 1.516(4) ?
  C4' C4'A . 1.520(4) ?
  C4'A C8'A . 1.521(4) ?
  C4'A C5' . 1.535(4) ?
  C5' C6' . 1.513(5) ?
  C6' C7' . 1.523(5) ?
  C7' C8' . 1.522(4) ?
  C8' C8'A . 1.517(4) ?
  C9' C10' . 1.508(4) ?
  O3 H3 . 0.80(3) ?
  O4 H4A . 0.86(3) ?
  O4 H4B . 0.86(3) ?
  O3' H3' . 0.89(3) ?
  O4' H4'A . 0.89(3) ?
  O4' H4'B . 0.81(3) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4C . 0.9700 ?
  C4 H4D . 0.9700 ?
  C4A H4AA . 0.9800 ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C3' H3'A . 0.9700 ?
  C3' H3'B . 0.9700 ?
  C4' H4'C . 0.9700 ?
  C4' H4'D . 0.9700 ?
  C4'A H4'E . 0.9800 ?
  C5' H5'A . 0.9700 ?
  C5' H5'B . 0.9700 ?
  C6' H6'A . 0.9700 ?
  C6' H6'B . 0.9700 ?
  C7' H7'A . 0.9700 ?
  C7' H7'B . 0.9700 ?
  C8' H8'A . 0.9700 ?
  C8' H8'B . 0.9700 ?
  C9' H9'A . 0.9700 ?
  C9' H9'B . 0.9700 ?