#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202235.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_2202235
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o889
_journal_page_last  o890
_publ_section_title
;
1(5),6(7)-Diepoxy-4-guaiol hemihydrate
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  'Xiang-Quan Ma'
  'Cheng-Zhu Liao'
  'Jing-Yu Su'
  'Long-Mei Zeng'
_chemical_name_common  'Singuaiol'
_chemical_formula_moiety  'C15 H24 O3, 0.5H2 O'
_chemical_formula_sum  'C15 H25 O3.5'
_chemical_formula_iupac  'C15 H24 O3, 0.5H2 O'
_chemical_formula_weight  261.35
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  10.3492(13)
_cell_length_b  9.9790(13)
_cell_length_c  14.6493(18)
_cell_angle_alpha  90.00
_cell_angle_beta  96.382(2)
_cell_angle_gamma  90.00
_cell_volume  1503.5(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.155
_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
  O1A 0.70920(18) 0.0826(2) 0.19439(13) 0.0557(5) Uani d . 1 . . O
  H1A 0.7783 0.0466 0.2201 0.080 Uiso d R 1 . . H
  O2A 0.48219(16) -0.0122(2) 0.35926(13) 0.0491(4) Uani d . 1 . . O
  O3A 0.38221(16) -0.1801(2) 0.20371(13) 0.0510(5) Uani d . 1 . . O
  C1A 0.7130(3) 0.0245(4) 0.4115(2) 0.0656(9) Uani d . 1 . . C
  H1AA 0.7037 0.0429 0.4748 0.080 Uiso d R 1 . . H
  H1AB 0.7986 -0.0103 0.4074 0.080 Uiso d R 1 . . H
  C2A 0.6903(3) 0.1507(4) 0.3541(2) 0.0664(9) Uani d . 1 . . C
  H2AA 0.7716 0.1928 0.3459 0.080 Uiso d R 1 . . H
  H2AB 0.6381 0.2132 0.3838 0.080 Uiso d R 1 . . H
  C3A 0.6211(3) 0.1082(3) 0.2614(2) 0.0503(6) Uani d . 1 . . C
  C4A 0.5562(2) -0.0254(3) 0.28154(17) 0.0416(5) Uani d . 1 . . C
  C5A 0.6115(2) -0.0740(3) 0.37257(17) 0.0473(6) Uani d . 1 . . C
  C6A 0.6167(3) -0.2147(4) 0.40948(19) 0.0562(7) Uani d . 1 . . C
  H6AA 0.7040 -0.2468 0.4086 0.080 Uiso d R 1 . . H
  C7A 0.5271(3) -0.3137(4) 0.3563(3) 0.0660(9) Uani d . 1 . . C
  H7AA 0.4399 -0.2799 0.3533 0.080 Uiso d R 1 . . H
  H7AB 0.5298 -0.3964 0.3899 0.080 Uiso d R 1 . . H
  C8A 0.5579(3) -0.3431(3) 0.2587(2) 0.0623(8) Uani d . 1 . . C
  H8AA 0.6094 -0.4191 0.2452 0.080 Uiso d R 1 . . H
  H8AB 0.4806 -0.3967 0.2487 0.080 Uiso d R 1 . . H
  C9A 0.5015(2) -0.2475(3) 0.1838(2) 0.0484(6) Uani d . 1 . . C
  C10A 0.4992(2) -0.1029(3) 0.19948(18) 0.0442(5) Uani d . 1 . . C
  H10A 0.4977 -0.0526 0.1435 0.080 Uiso d R 1 . . H
  C11A 0.5257(3) 0.2133(4) 0.2200(3) 0.0709(10) Uani d . 1 . . C
  H11A 0.5717 0.2942 0.2090 0.080 Uiso d R 1 . . H
  H11B 0.4824 0.1805 0.1630 0.080 Uiso d R 1 . . H
  H11C 0.4625 0.2314 0.2617 0.080 Uiso d R 1 . . H
  C12A 0.5886(4) -0.2103(6) 0.5107(3) 0.0930(14) Uani d . 1 . . C
  H12A 0.6462 -0.1472 0.5436 0.080 Uiso d R 1 . . H
  H12B 0.5002 -0.1829 0.5136 0.080 Uiso d R 1 . . H
  H12C 0.6019 -0.2975 0.5378 0.080 Uiso d R 1 . . H
  C13A 0.5004(3) -0.2928(4) 0.0849(2) 0.0616(8) Uani d . 1 . . C
  H13A 0.4615 -0.2215 0.0474 0.080 Uiso d R 1 . . H
  C14A 0.6379(4) -0.3082(7) 0.0607(3) 0.1008(17) Uani d . 1 . . C
  H14A 0.6354 -0.3369 -0.0021 0.080 Uiso d R 1 . . H
  H14B 0.6823 -0.2238 0.0683 0.080 Uiso d R 1 . . H
  H14C 0.6832 -0.3738 0.1002 0.080 Uiso d R 1 . . H
  C15A 0.4162(4) -0.4159(5) 0.0621(3) 0.0881(12) Uani d . 1 . . C
  H15A 0.4189 -0.4404 -0.0011 0.080 Uiso d R 1 . . H
  H15B 0.4483 -0.4888 0.1010 0.080 Uiso d R 1 . . H
  H15C 0.3282 -0.3963 0.0724 0.080 Uiso d R 1 . . H
  O1B 1.15198(18) -0.1477(3) 0.08521(13) 0.0591(6) Uani d . 1 . . O
  O2B 0.95868(17) -0.0122(2) 0.25933(13) 0.0513(5) Uani d . 1 . . O
  H1B 1.2215 -0.1428 0.1216 0.080 Uiso d R 1 . . H
  O3B 0.89470(19) -0.2958(3) 0.27388(16) 0.0626(6) Uani d . 1 . . O
  C1B 1.1761(3) 0.0758(3) 0.2399(2) 0.0550(7) Uani d . 1 . . C
  H1BA 1.1690 0.1608 0.2696 0.080 Uiso d R 1 . . H
  H1BB 1.2662 0.0513 0.2435 0.080 Uiso d R 1 . . H
  C2B 1.1160(3) 0.0812(4) 0.1387(2) 0.0645(8) Uani d . 1 . . C
  H2BA 1.1808 0.1031 0.0990 0.080 Uiso d R 1 . . H
  H2BB 1.0488 0.1478 0.1313 0.080 Uiso d R 1 . . H
  C3B 1.0592(3) -0.0579(3) 0.11682(18) 0.0514(7) Uani d . 1 . . C
  C4B 1.0271(2) -0.1108(3) 0.21055(16) 0.0408(5) Uani d . 1 . . C
  C5B 1.0991(2) -0.0305(3) 0.28343(17) 0.0417(5) Uani d . 1 . . C
  C6B 1.1434(3) -0.0689(3) 0.38171(18) 0.0506(6) Uani d . 1 . . C
  H6BA 1.2354 -0.0847 0.3858 0.080 Uiso d R 1 . . H
  C7B 1.0820(3) -0.1945(4) 0.41605(18) 0.0554(7) Uani d . 1 . . C
  H7BA 0.9895 -0.1817 0.4105 0.080 Uiso d R 1 . . H
  H7BB 1.1112 -0.2052 0.4801 0.080 Uiso d R 1 . . H
  C8B 1.1106(3) -0.3220(3) 0.3663(2) 0.0590(7) Uani d . 1 . . C
  H8BA 1.1811 -0.3796 0.3891 0.080 Uiso d R 1 . . H
  H8BB 1.0534 -0.3702 0.4018 0.080 Uiso d R 1 . . H
  C9B 1.0226(3) -0.3559(3) 0.27959(19) 0.0499(6) Uani d . 1 . . C
  C10B 0.9826(2) -0.2537(3) 0.21096(19) 0.0483(6) Uani d . 1 . . C
  H10B 0.9616 -0.2898 0.1504 0.080 Uiso d R 1 . . H
  C11B 0.9447(3) -0.0539(4) 0.0422(2) 0.0696(10) Uani d . 1 . . C
  H11D 0.9730 -0.0197 -0.0135 0.080 Uiso d R 1 . . H
  H11E 0.9105 -0.1426 0.0317 0.080 Uiso d R 1 . . H
  H11F 0.8783 0.0035 0.0614 0.080 Uiso d R 1 . . H
  C12B 1.1224(4) 0.0499(4) 0.4450(3) 0.0790(11) Uani d . 1 . . C
  H12D 1.1619 0.1287 0.4228 0.080 Uiso d R 1 . . H
  H12E 1.0308 0.0648 0.4456 0.080 Uiso d R 1 . . H
  H12F 1.1611 0.0304 0.5062 0.080 Uiso d R 1 . . H
  C13B 1.0234(4) -0.4995(3) 0.2462(2) 0.0664(8) Uani d . 1 . . C
  H13B 0.9660 -0.5034 0.1901 0.080 Uiso d R 1 . . H
  C14B 1.1578(4) -0.5380(4) 0.2229(3) 0.0838(12) Uani d . 1 . . C
  H14D 1.1569 -0.6291 0.2017 0.080 Uiso d R 1 . . H
  H14E 1.1818 -0.4798 0.1754 0.080 Uiso d R 1 . . H
  H14F 1.2195 -0.5290 0.2765 0.080 Uiso d R 1 . . H
  C15B 0.9711(5) -0.5981(5) 0.3111(3) 0.0942(14) Uani d . 1 . . C
  H15D 0.9739 -0.6872 0.2866 0.080 Uiso d R 1 . . H
  H15E 1.0236 -0.5940 0.3693 0.080 Uiso d R 1 . . H
  H15F 0.8829 -0.5754 0.3191 0.080 Uiso d R 1 . . H
  O1W 1.2145(5) -0.1662(5) -0.1012(3) 0.160(2) Uani d . 1 . . O
  H1WA 1.1963 -0.1621 -0.0454 0.150 Uiso d R 1 . . H
  H1WB 1.2364 -0.2389 -0.1271 0.150 Uiso d 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
  O1A 0.0437(9) 0.0702(13) 0.0550(10) 0.0048(9) 0.0140(8) 0.0112(10)
  O2A 0.0383(9) 0.0605(11) 0.0501(10) 0.0000(8) 0.0115(7) -0.0045(9)
  O3A 0.0337(8) 0.0604(11) 0.0579(10) 0.0013(8) 0.0004(7) -0.0085(9)
  C1A 0.0515(16) 0.093(3) 0.0517(16) -0.0161(16) 0.0049(12) -0.0124(16)
  C2A 0.0583(17) 0.070(2) 0.073(2) -0.0209(16) 0.0199(15) -0.0186(18)
  C3A 0.0420(13) 0.0496(15) 0.0612(16) -0.0007(11) 0.0140(11) -0.0005(13)
  C4A 0.0332(11) 0.0480(14) 0.0444(12) 0.0025(11) 0.0072(9) 0.0008(11)
  C5A 0.0353(11) 0.0663(17) 0.0408(12) -0.0012(12) 0.0070(9) -0.0006(12)
  C6A 0.0468(14) 0.073(2) 0.0490(15) 0.0065(13) 0.0066(11) 0.0159(14)
  C7A 0.0531(16) 0.065(2) 0.079(2) -0.0044(15) 0.0046(14) 0.0285(17)
  C8A 0.0612(18) 0.0455(15) 0.078(2) 0.0058(14) -0.0026(15) -0.0025(15)
  C9A 0.0338(11) 0.0524(15) 0.0586(16) 0.0005(11) 0.0026(11) -0.0063(13)
  C10A 0.0385(12) 0.0499(14) 0.0437(12) 0.0029(11) 0.0033(9) 0.0035(11)
  C11A 0.0545(17) 0.0518(18) 0.109(3) 0.0077(14) 0.0217(18) 0.0119(18)
  C12A 0.105(3) 0.120(4) 0.0568(19) 0.004(3) 0.0212(19) 0.028(2)
  C13A 0.0489(15) 0.072(2) 0.0635(17) -0.0039(14) 0.0070(13) -0.0188(15)
  C14A 0.061(2) 0.154(5) 0.090(3) -0.005(3) 0.0208(19) -0.039(3)
  C15A 0.098(3) 0.089(3) 0.078(2) -0.022(2) 0.011(2) -0.031(2)
  O1B 0.0438(10) 0.0900(17) 0.0441(9) 0.0126(10) 0.0070(8) -0.0081(10)
  O2B 0.0364(9) 0.0658(12) 0.0524(10) 0.0129(9) 0.0076(7) -0.0024(9)
  O3B 0.0392(9) 0.0775(14) 0.0719(13) -0.0096(10) 0.0095(9) 0.0069(11)
  C1B 0.0545(15) 0.0459(15) 0.0658(17) -0.0024(13) 0.0127(13) 0.0017(13)
  C2B 0.0695(19) 0.0629(19) 0.0629(18) 0.0045(16) 0.0146(15) 0.0203(16)
  C3B 0.0464(13) 0.0659(17) 0.0425(13) 0.0117(13) 0.0079(10) 0.0075(12)
  C4B 0.0325(10) 0.0499(13) 0.0401(12) 0.0075(10) 0.0044(9) 0.0018(11)
  C5B 0.0339(11) 0.0461(14) 0.0456(12) 0.0047(10) 0.0069(9) -0.0011(11)
  C6B 0.0426(13) 0.0656(18) 0.0425(13) -0.0053(12) -0.0007(10) -0.0041(12)
  C7B 0.0602(16) 0.0686(19) 0.0367(12) -0.0045(14) 0.0014(11) 0.0020(12)
  C8B 0.0580(16) 0.0597(18) 0.0564(16) 0.0034(14) -0.0059(13) 0.0096(14)
  C9B 0.0467(13) 0.0543(15) 0.0497(14) -0.0084(12) 0.0101(11) 0.0017(12)
  C10B 0.0405(12) 0.0605(16) 0.0427(13) -0.0075(12) -0.0006(10) -0.0019(12)
  C11B 0.0580(17) 0.102(3) 0.0470(15) 0.0172(18) 0.0000(12) 0.0169(17)
  C12B 0.099(3) 0.079(2) 0.0585(19) -0.023(2) 0.0093(18) -0.0213(18)
  C13B 0.083(2) 0.0536(17) 0.0640(18) -0.0177(16) 0.0155(16) -0.0003(15)
  C14B 0.106(3) 0.054(2) 0.097(3) -0.0022(19) 0.039(2) -0.0026(19)
  C15B 0.120(4) 0.066(2) 0.103(3) -0.031(2) 0.045(3) 0.000(2)
  O1W 0.268(6) 0.134(4) 0.085(2) 0.082(4) 0.052(3) 0.008(2)
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
  O1A C3A . 1.435(3) ?
  O1A H1A . 0.8500 ?
  O2A C4A . 1.447(3) ?
  O2A C5A . 1.467(3) ?
  O3A C10A . 1.442(3) ?
  O3A C9A . 1.463(3) ?
  C1A C5A . 1.503(4) ?
  C1A C2A . 1.518(6) ?
  C1A H1AA . 0.9601 ?
  C1A H1AB . 0.9600 ?
  C2A C3A . 1.524(5) ?
  C2A H2AA . 0.9598 ?
  C2A H2AB . 0.9601 ?
  C3A C11A . 1.520(4) ?
  C3A C4A . 1.536(4) ?
  C4A C5A . 1.473(4) ?
  C4A C10A . 1.495(4) ?
  C5A C6A . 1.504(5) ?
  C6A C7A . 1.511(5) ?
  C6A C12A . 1.543(4) ?
  C6A H6AA . 0.9600 ?
  C7A C8A . 1.527(5) ?
  C7A H7AA . 0.9600 ?
  C7A H7AB . 0.9600 ?
  C8A C9A . 1.520(4) ?
  C8A H8AA . 0.9600 ?
  C8A H8AB . 0.9599 ?
  C9A C10A . 1.462(4) ?
  C9A C13A . 1.517(4) ?
  C10A H10A . 0.9600 ?
  C11A H11A . 0.9601 ?
  C11A H11B . 0.9603 ?
  C11A H11C . 0.9597 ?
  C12A H12A . 0.9600 ?
  C12A H12B . 0.9600 ?
  C12A H12C . 0.9600 ?
  C13A C14A . 1.513(5) ?
  C13A C15A . 1.522(5) ?
  C13A H13A . 0.9600 ?
  C14A H14A . 0.9601 ?
  C14A H14B . 0.9600 ?
  C14A H14C . 0.9600 ?
  C15A H15A . 0.9601 ?
  C15A H15B . 0.9601 ?
  C15A H15C . 0.9600 ?
  O1B C3B . 1.428(3) ?
  O1B H1B . 0.8481 ?
  O2B C4B . 1.447(3) ?
  O2B C5B . 1.468(3) ?
  O3B C10B . 1.429(3) ?
  O3B C9B . 1.448(4) ?
  C1B C5B . 1.510(4) ?
  C1B C2B . 1.543(5) ?
  C1B H1BA . 0.9600 ?
  C1B H1BB . 0.9597 ?
  C2B C3B . 1.528(5) ?
  C2B H2BA . 0.9601 ?
  C2B H2BB . 0.9601 ?
  C3B C11B . 1.520(4) ?
  C3B C4B . 1.541(4) ?
  C4B C5B . 1.469(4) ?
  C4B C10B . 1.499(4) ?
  C5B C6B . 1.511(4) ?
  C6B C7B . 1.516(4) ?
  C6B C12B . 1.536(5) ?
  C6B H6BA . 0.9600 ?
  C7B C8B . 1.512(5) ?
  C7B H7BA . 0.9600 ?
  C7B H7BB . 0.9599 ?
  C8B C9B . 1.516(4) ?
  C8B H8BA . 0.9600 ?
  C8B H8BB . 0.9600 ?
  C9B C10B . 1.460(4) ?
  C9B C13B . 1.514(5) ?
  C10B H10B . 0.9600 ?
  C11B H11D . 0.9601 ?
  C11B H11E . 0.9600 ?
  C11B H11F . 0.9600 ?
  C12B H12D . 0.9600 ?
  C12B H12E . 0.9602 ?
  C12B H12F . 0.9600 ?
  C13B C15B . 1.510(5) ?
  C13B C14B . 1.518(5) ?
  C13B H13B . 0.9599 ?
  C14B H14D . 0.9600 ?
  C14B H14E . 0.9601 ?
  C14B H14F . 0.9601 ?
  C15B H15D . 0.9601 ?
  C15B H15E . 0.9599 ?
  C15B H15F . 0.9600 ?
  O1W H1WA . 0.8600 ?
  O1W H1WB . 0.8606 ?
_cod_database_code 2202235