data_2200178 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o172 _journal_page_last o173 _publ_section_title ; Redetermination of 3,3,6,6-tetramethyl-4a-hydroxy-9-(ortho-methoxyphenyl)- 2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthene-1,8-dione at 173 K ; loop_ _publ_author_name 'Bolte, Michael' 'Degen, Alexander' 'R\"uhl, Stephan' _chemical_formula_moiety 'C24 H30 O5' _chemical_formula_sum 'C24 H30 O5' _chemical_formula_weight 398.48 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.845(4) _cell_length_b 7.2140(10) _cell_length_c 22.605(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.820(10) _cell_angle_gamma 90.00 _cell_volume 4300.1(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.231 _diffrn_ambient_temperature 173(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 .12122(4) .66923(16) .04378(6) .0188(2) Uani d . 1 . . C H1 .1138 .7884 .0159 .023 Uiso calc R 1 . . H C11 .17833(4) .65689(16) .10174(6) .0200(2) Uani d . 1 . . C C12 .20475(4) .51162(17) .10450(6) .0201(2) Uani d . 1 . . C O12 .18343(3) .35659(12) .06152(5) .02137(19) Uani d . 1 . . O C13 .26153(4) .50279(18) .15320(7) .0246(3) Uani d . 1 . . C H13A .2708 .4369 .1251 .030 Uiso calc R 1 . . H H13B .2749 .4301 .1995 .030 Uiso calc R 1 . . H C14 .28656(5) .69446(19) .17659(7) .0263(3) Uani d . 1 . . C C17 .27656(6) .7943(2) .10856(9) .0406(4) Uani d . 1 . . C H17A .2928 .9164 .1245 .061 Uiso calc R 1 . . H H17B .2399 .8095 .0686 .061 Uiso calc R 1 . . H H17C .2905 .7210 .0890 .061 Uiso calc R 1 . . H C18 .34396(5) .6714(2) .23959(9) .0366(3) Uani d . 1 . . C H18A .3602 .7936 .2548 .055 Uiso calc R 1 . . H H18B .3580 .5959 .2207 .055 Uiso calc R 1 . . H H18C .3503 .6100 .2835 .055 Uiso calc R 1 . . H C15 .26359(5) .80402(19) .20666(8) .0281(3) Uani d . 1 . . C H15A .2730 .7429 .2531 .034 Uiso calc R 1 . . H H15B .2782 .9304 .2207 .034 Uiso calc R 1 . . H C16 .20637(4) .81829(17) .14927(7) .0212(2) Uani d . 1 . . C O16 .18464(3) .96186(12) .14399(5) .0268(2) Uani d . 1 . . O C21 .10176(4) .51451(16) -.01524(6) .0193(2) Uani d . 1 . . C H21 .0649 .4953 -.0414 .023 Uiso calc R 1 . . H C22 .12931(4) .32929(16) .02023(6) .0187(2) Uani d . 1 . . C O22 .12165(3) .27385(12) .07151(5) .02163(19) Uani d . 1 . . O H22 .1380 .1760 .0934 .026 Uiso calc R 1 . . H C23 .11263(5) .17950(17) -.03909(7) .0216(2) Uani d . 1 . . C H23A .0783 .1374 -.0598 .026 Uiso calc R 1 . . H H23B .1358 .0723 -.0129 .026 Uiso calc R 1 . . H C24 .11117(5) .23308(18) -.10672(7) .0256(3) Uani d . 1 . . C C27 .16458(6) .2393(2) -.08351(9) .0346(3) Uani d . 1 . . C H27A .1850 .3319 -.0434 .052 Uiso calc R 1 . . H H27B .1623 .2727 -.1276 .052 Uiso calc R 1 . . H H27C .1806 .1172 -.0647 .052 Uiso calc R 1 . . H C28 .07951(6) .0878(2) -.16954(8) .0363(3) Uani d . 1 . . C H28A .0453 .0831 -.1847 .054 Uiso calc R 1 . . H H28B .0956 -.0340 -.1506 .054 Uiso calc R 1 . . H H28C .0774 .1216 -.2135 .054 Uiso calc R 1 . . H C25 .08516(5) .42429(19) -.13828(7) .0297(3) Uani d . 1 . . C H25A .0895 .4683 -.1754 .036 Uiso calc R 1 . . H H25B .0484 .4115 -.1651 .036 Uiso calc R 1 . . H C26 .10745(5) .56471(18) -.07526(7) .0243(3) Uani d . 1 . . C O26 .12935(4) .70318(14) -.07108(6) .0354(2) Uani d . 1 . . O C31 .09319(4) .67912(16) .07631(7) .0200(2) Uani d . 1 . . C C32 .04118(4) .72515(17) .02731(7) .0223(2) Uani d . 1 . . C O321 .02079(3) .75913(13) -.04656(5) .0274(2) Uani d . 1 . . O C321 -.03313(5) .7844(2) -.10058(8) .0314(3) Uani d . 1 . . C H32A -.0432 .7984 -.1515 .047 Uiso calc R 1 . . H H32B -.0428 .8958 -.0875 .047 Uiso calc R 1 . . H H32C -.0502 .6762 -.0996 .047 Uiso calc R 1 . . H C33 .01372(5) .73613(18) .05401(8) .0274(3) Uani d . 1 . . C H33 -.0215 .7629 .0201 .033 Uiso calc R 1 . . H C34 .03847(5) .7076(2) .13078(8) .0304(3) Uani d . 1 . . C H34 .0200 .7164 .1494 .036 Uiso calc R 1 . . H C35 .08967(5) .66640(19) .18022(8) .0290(3) Uani d . 1 . . C H35 .1065 .6485 .2327 .035 Uiso calc R 1 . . H C36 .11644(5) .65137(17) .15230(7) .0242(3) Uani d . 1 . . C H36 .1515 .6213 .1863 .029 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 C1 .0164(5) .0183(5) .0206(5) .0020(4) .0110(5) .0019(4) C11 .0173(5) .0219(6) .0210(5) .0005(4) .0122(5) .0015(4) C12 .0186(5) .0227(6) .0195(5) -.0002(4) .0121(5) .0007(4) O12 .0167(4) .0210(4) .0254(4) .0014(3) .0128(4) -.0011(3) C13 .0171(5) .0272(6) .0279(6) .0026(5) .0133(5) -.0009(5) C14 .0180(6) .0301(7) .0296(6) -.0024(5) .0143(5) -.0038(5) C17 .0353(8) .0478(9) .0471(9) -.0042(7) .0299(7) .0063(7) C18 .0181(6) .0434(8) .0398(8) -.0029(6) .0140(6) -.0114(6) C15 .0185(6) .0304(7) .0277(6) -.0010(5) .0108(5) -.0071(5) C16 .0203(6) .0230(6) .0212(5) .0003(5) .0134(5) .0009(5) O16 .0254(4) .0223(4) .0286(5) .0029(3) .0149(4) -.0006(4) C21 .0171(5) .0209(6) .0193(5) .0025(4) .0111(4) .0020(4) C22 .0171(5) .0201(5) .0200(5) .0006(4) .0122(5) .0014(4) O22 .0242(4) .0228(4) .0220(4) .0037(3) .0165(4) .0048(3) C23 .0230(6) .0203(6) .0224(6) -.0008(4) .0147(5) -.0002(5) C24 .0315(6) .0260(6) .0232(6) .0030(5) .0190(6) .0013(5) C27 .0402(8) .0406(8) .0383(8) .0061(6) .0319(7) .0037(6) C28 .0499(9) .0307(7) .0267(7) .0017(6) .0232(7) -.0021(6) C25 .0389(7) .0296(7) .0233(6) .0061(6) .0208(6) .0042(5) C26 .0272(6) .0233(6) .0245(6) .0084(5) .0171(5) .0076(5) O26 .0504(6) .0276(5) .0419(6) .0003(4) .0355(5) .0055(4) C31 .0186(5) .0175(5) .0251(6) .0000(4) .0142(5) -.0019(4) C32 .0196(6) .0204(6) .0245(6) -.0003(4) .0127(5) -.0020(4) O321 .0164(4) .0352(5) .0243(4) .0052(4) .0097(4) .0033(4) C321 .0167(6) .0320(7) .0302(7) .0036(5) .0072(5) .0012(5) C33 .0204(6) .0268(6) .0367(7) -.0003(5) .0187(6) -.0047(5) C34 .0331(7) .0310(7) .0401(7) -.0035(5) .0292(6) -.0068(6) C35 .0345(7) .0307(7) .0274(6) -.0024(5) .0220(6) -.0034(5) C36 .0218(6) .0249(6) .0245(6) .0005(5) .0138(5) -.0001(5) 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 C11 . 1.5118(15) ? C1 C31 . 1.5233(16) ? C1 C21 . 1.5356(16) ? C1 H1 . 1.0000 ? C11 C12 . 1.3533(17) ? C11 C16 . 1.4602(17) ? C12 O12 . 1.3551(14) ? C12 C13 . 1.5021(16) ? O12 C22 . 1.4567(13) ? C13 C14 . 1.5322(18) ? C13 H13A . .9900 ? C13 H13B . .9900 ? C14 C17 . 1.531(2) ? C14 C15 . 1.5342(18) ? C14 C18 . 1.5366(18) ? C17 H17A . .9800 ? C17 H17B . .9800 ? C17 H17C . .9800 ? C18 H18A . .9800 ? C18 H18B . .9800 ? C18 H18C . .9800 ? C15 C16 . 1.5145(16) ? C15 H15A . .9900 ? C15 H15B . .9900 ? C16 O16 . 1.2322(15) ? C21 C26 . 1.5284(16) ? C21 C22 . 1.5363(16) ? C21 H21 . 1.0000 ? C22 O22 . 1.3956(14) ? C22 C23 . 1.5281(16) ? O22 H22 . .8400 ? C23 C24 . 1.5474(17) ? C23 H23A . .9900 ? C23 H23B . .9900 ? C24 C28 . 1.5346(19) ? C24 C27 . 1.5347(19) ? C24 C25 . 1.5490(18) ? C27 H27A . .9800 ? C27 H27B . .9800 ? C27 H27C . .9800 ? C28 H28A . .9800 ? C28 H28B . .9800 ? C28 H28C . .9800 ? C25 C26 . 1.5091(19) ? C25 H25A . .9900 ? C25 H25B . .9900 ? C26 O26 . 1.2118(16) ? C31 C36 . 1.3840(17) ? C31 C32 . 1.4111(16) ? C32 O321 . 1.3712(15) ? C32 C33 . 1.3918(17) ? O321 C321 . 1.4356(15) ? C321 H32A . .9800 ? C321 H32B . .9800 ? C321 H32C . .9800 ? C33 C34 . 1.390(2) ? C33 H33 . .9500 ? C34 C35 . 1.382(2) ? C34 H34 . .9500 ? C35 C36 . 1.3957(18) ? C35 H35 . .9500 ? C36 H36 . .9500 ?