data_2011912 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 444 _journal_page_last 445 _publ_section_title ; Two diastereomers of 9-(2,6-dichlorophenyl)-4a-hydroxy-3,3,6,6-tetramethyl- 1,2,3,4,4a,5,6,7,8,9a-decahydroxanthene-1,8-dione in the same crystal ; loop_ _publ_author_name 'Bolte, Michael' 'Degen, Alexander' 'R\"uhl, Stephan' _chemical_formula_moiety 'C23 H26 Cl2 O4' _chemical_formula_sum 'C23 H26 Cl2 O4' _chemical_formula_weight 437.34 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.936(3) _cell_length_b 12.969(4) _cell_length_c 16.204(5) _cell_angle_alpha 74.500(10) _cell_angle_beta 90.160(10) _cell_angle_gamma 65.500(10) _cell_volume 2180.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.332 _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 .4942(4) .3174(3) .7797(2) .0277(9) Uani d . 1 . . C H1 .4808 .3809 .8078 .033 Uiso calc R 1 . . H C11 .4188(4) .2546(4) .8236(3) .0304(9) Uani d . 1 . . C C12 .3335(4) .2406(4) .7800(3) .0302(9) Uani d . 1 . . C O12 .3118(3) .2712(3) .69313(18) .0326(7) Uani d . 1 . . O C13 .2492(4) .1880(4) .8212(3) .0380(10) Uani d . 1 . . C H13C .2860 .1026 .8256 .046 Uiso calc R 1 . . H H13D .1684 .2269 .7839 .046 Uiso calc R 1 . . H C14 .2275(4) .2027(4) .9113(3) .0378(10) Uani d . 1 . . C C17 .1642(5) .1252(5) .9563(3) .0537(14) Uani d . 1 . . C H17D .0831 .1519 .9234 .080 Uiso calc R 1 . . H H17E .1528 .1319 1.0148 .080 Uiso calc R 1 . . H H17F .2162 .0424 .9593 .080 Uiso calc R 1 . . H C18 .1457(5) .3325(5) .9046(4) .0589(15) Uani d . 1 . . C H18D .1863 .3817 .8754 .088 Uiso calc R 1 . . H H18E .1333 .3409 .9627 .088 Uiso calc R 1 . . H H18F .0651 .3583 .8714 .088 Uiso calc R 1 . . H C15 .3535(4) .1624(5) .9613(3) .0424(11) Uani d . 1 . . C H15C .3405 .1806 1.0170 .051 Uiso calc R 1 . . H H15D .3987 .0752 .9744 .051 Uiso calc R 1 . . H C16 .4337(4) .2168(4) .9164(3) .0343(10) Uani d . 1 . . C O16 .5134(3) .2267(3) .95794(19) .0442(8) Uani d . 1 . . O C21 .4349(4) .3842(3) .6848(3) .0271(9) Uani d . 1 . . C H21 .4999 .4001 .6522 .033 Uiso calc R 1 . . H C22 .3957(4) .3101(3) .6425(3) .0273(9) Uani d . 1 . . C O22 .5024(2) .2107(2) .64128(19) .0338(7) Uani d . 1 . . O H22 .4825 .1605 .6300 .041 Uiso calc R 1 . . H C23 .3227(4) .3780(3) .5535(3) .0282(9) Uani d . 1 . . C H23C .2878 .3287 .5360 .034 Uiso calc R 1 . . H H23D .3814 .3880 .5126 .034 Uiso calc R 1 . . H C24 .2152(4) .5017(4) .5433(3) .0317(10) Uani d . 1 . . C C27 .1046(4) .4933(4) .5866(3) .0451(12) Uani d . 1 . . C H27D .1310 .4518 .6484 .068 Uiso calc R 1 . . H H27E .0727 .4493 .5603 .068 Uiso calc R 1 . . H H27F .0391 .5732 .5790 .068 Uiso calc R 1 . . H C28 .1753(4) .5659(4) .4471(3) .0398(11) Uani d . 1 . . C H28D .2468 .5709 .4198 .060 Uiso calc R 1 . . H H28E .1100 .6460 .4392 .060 Uiso calc R 1 . . H H28F .1436 .5221 .4205 .060 Uiso calc R 1 . . H C25 .2648(4) .5711(4) .5839(3) .0378(11) Uani d . 1 . . C H25C .3255 .5894 .5487 .045 Uiso calc R 1 . . H H25D .1952 .6472 .5835 .045 Uiso calc R 1 . . H C26 .3257(4) .5035(4) .6747(3) .0328(10) Uani d . 1 . . C O26 .2924(3) .5399(3) .7358(2) .0480(9) Uani d . 1 . . O C31 .6331(4) .2494(3) .7869(2) .0277(9) Uani d . 1 . . C C32 .7058(4) .3126(4) .7741(3) .0314(9) Uani d . 1 . . C Cl2 .63358(10) .46609(9) .75792(8) .0422(3) Uani d . 1 . . Cl C33 .8314(4) .2639(4) .7732(3) .0389(11) Uani d . 1 . . C H33 .8744 .3125 .7628 .047 Uiso calc R 1 . . H C34 .8954(4) .1423(4) .7876(3) .0429(11) Uani d . 1 . . C H34 .9826 .1066 .7864 .052 Uiso calc R 1 . . H C35 .8303(4) .0745(4) .8037(3) .0381(11) Uani d . 1 . . C H35 .8732 -.0089 .8146 .046 Uiso calc R 1 . . H C36 .7035(4) .1263(4) .8042(3) .0341(10) Uani d . 1 . . C Cl6 .63513(11) .02788(9) .82867(8) .0406(3) Uani d . 1 . . Cl C1A .3396(4) .8963(3) .6989(2) .0267(9) Uani d . 1 . . C H1A .2986 .9691 .7180 .032 Uiso calc R 1 . . H C11A .4774(4) .8648(3) .7046(2) .0257(9) Uani d . 1 . . C C12A .5592(4) .7733(4) .7702(3) .0272(9) Uani d . 1 . . C O12A .5274(2) .7055(2) .83566(18) .0318(7) Uani d . 1 . . O C13A .6947(4) .7390(4) .7814(3) .0315(9) Uani d . 1 . . C H13A .7388 .6516 .8053 .038 Uiso calc R 1 . . H H13B .7124 .7737 .8245 .038 Uiso calc R 1 . . H C14A .7474(4) .7773(4) .6994(3) .0310(9) Uani d . 1 . . C C17A .8761(4) .7653(4) .7239(3) .0417(11) Uani d . 1 . . C H17A .9106 .7900 .6714 .063 Uiso calc R 1 . . H H17B .9301 .6824 .7553 .063 Uiso calc R 1 . . H H17C .8706 .8156 .7607 .063 Uiso calc R 1 . . H C18A .7580(4) .6982(4) .6421(3) .0409(11) Uani d . 1 . . C H18A .6756 .7045 .6263 .061 Uiso calc R 1 . . H H18B .8132 .6157 .6735 .061 Uiso calc R 1 . . H H18C .7921 .7237 .5896 .061 Uiso calc R 1 . . H C15A .6587(4) .9071(4) .6500(3) .0324(10) Uani d . 1 . . C H15A .6778 .9597 .6761 .039 Uiso calc R 1 . . H H15B .6774 .9232 .5897 .039 Uiso calc R 1 . . H C16A .5222(4) .9409(4) .6480(3) .0298(9) Uani d . 1 . . C O16A .4482(3) 1.0390(2) .59961(19) .0363(7) Uani d . 1 . . O C21A .3180(3) .7969(3) .7630(2) .0256(8) Uani d . 1 . . C H21A .3458 .7282 .7388 .031 Uiso calc R 1 . . H C22A .3979(4) .7555(4) .8492(3) .0300(9) Uani d . 1 . . C O22A .3734(3) .8548(2) .87668(18) .0320(7) Uani d . 1 . . O H22A .4107 .8334 .9266 .038 Uiso calc R 1 . . H C23A .3829(4) .6553(4) .9144(3) .0328(10) Uani d . 1 . . C H23A .4338 .6353 .9697 .039 Uiso calc R 1 . . H H23B .4155 .5844 .8936 .039 Uiso calc R 1 . . H C24A .2488(4) .6839(4) .9312(3) .0338(10) Uani d . 1 . . C C27A .2441(5) .5682(5) .9845(3) .0523(13) Uani d . 1 . . C H27A .1588 .5847 .9961 .078 Uiso calc R 1 . . H H27B .2987 .5362 1.0393 .078 Uiso calc R 1 . . H H27C .2719 .5101 .9520 .078 Uiso calc R 1 . . H C28A .1992(4) .7749(5) .9819(3) .0469(12) Uani d . 1 . . C H28A .1131 .7903 .9907 .070 Uiso calc R 1 . . H H28B .2023 .8489 .9492 .070 Uiso calc R 1 . . H H28C .2504 .7435 1.0380 .070 Uiso calc R 1 . . H C25A .1652(4) .7321(4) .8448(3) .0327(10) Uani d . 1 . . C H25A .1811 .6657 .8204 .039 Uiso calc R 1 . . H H25B .0774 .7636 .8556 .039 Uiso calc R 1 . . H C26A .1841(4) .8280(4) .7793(3) .0292(9) Uani d . 1 . . C O26A .0997(3) .9216(3) .7402(2) .0428(8) Uani d . 1 . . O C31A .2781(4) .9254(4) .6079(3) .0287(9) Uani d . 1 . . C C32A .1761(4) 1.0334(4) .5675(3) .0321(10) Uani d . 1 . . C Cl3A .12852(11) 1.14906(10) .61450(8) .0473(3) Uani d . 1 . . Cl C33A .1093(4) 1.0563(4) .4905(3) .0389(11) Uani d . 1 . . C H33A .0386 1.1298 .4673 .047 Uiso calc R 1 . . H C34A .1455(4) .9715(4) .4463(3) .0394(11) Uani d . 1 . . C H34A .0983 .9856 .3938 .047 Uiso calc R 1 . . H C35A .2503(4) .8670(4) .4796(3) .0362(10) Uani d . 1 . . C H35A .2791 .8102 .4486 .043 Uiso calc R 1 . . H C36A .3132(4) .8454(3) .5583(3) .0270(9) Uani d . 1 . . C Cl6A .44433(9) .71079(9) .59683(7) .0333(3) Uani d . 1 . . Cl 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 .040(2) .023(2) .025(2) -.0160(18) .0064(18) -.0102(17) C11 .036(2) .029(2) .032(2) -.0148(18) .0110(18) -.0159(19) C12 .037(2) .027(2) .032(2) -.0159(18) .0103(18) -.0144(18) O12 .0428(17) .0320(16) .0299(16) -.0214(14) .0054(13) -.0114(13) C13 .048(3) .041(3) .037(3) -.028(2) .009(2) -.016(2) C14 .039(2) .046(3) .035(3) -.021(2) .013(2) -.019(2) C17 .052(3) .076(4) .041(3) -.039(3) .013(2) -.013(3) C18 .049(3) .061(4) .075(4) -.023(3) .022(3) -.036(3) C15 .049(3) .052(3) .031(3) -.027(2) .011(2) -.011(2) C16 .034(2) .039(3) .032(2) -.016(2) .0043(19) -.013(2) O16 .052(2) .059(2) .0290(17) -.0311(18) .0027(15) -.0143(16) C21 .033(2) .022(2) .032(2) -.0145(17) .0085(17) -.0130(18) C22 .030(2) .025(2) .031(2) -.0123(17) .0084(17) -.0128(18) O22 .0394(16) .0199(15) .0400(18) -.0064(13) .0030(13) -.0162(13) C23 .034(2) .025(2) .029(2) -.0126(18) .0066(17) -.0118(18) C24 .033(2) .023(2) .040(3) -.0090(18) .0017(19) -.0140(19) C27 .034(2) .050(3) .049(3) -.012(2) .003(2) -.020(2) C28 .040(3) .031(2) .043(3) -.008(2) .000(2) -.013(2) C25 .039(2) .026(2) .047(3) -.0091(19) -.001(2) -.016(2) C26 .034(2) .026(2) .043(3) -.0129(18) .0043(19) -.019(2) O26 .052(2) .0377(19) .054(2) -.0080(15) .0041(16) -.0307(17) C31 .033(2) .026(2) .025(2) -.0115(17) .0041(17) -.0109(17) C32 .040(2) .029(2) .031(2) -.0175(19) .0063(19) -.0144(19) Cl2 .0454(7) .0272(6) .0587(8) -.0191(5) .0044(5) -.0142(5) C33 .046(3) .037(3) .036(3) -.020(2) .008(2) -.011(2) C34 .034(2) .044(3) .046(3) -.010(2) .007(2) -.018(2) C35 .041(3) .028(2) .041(3) -.009(2) .001(2) -.013(2) C36 .050(3) .026(2) .030(2) -.018(2) .003(2) -.0112(18) Cl6 .0541(7) .0259(6) .0451(7) -.0190(5) .0074(5) -.0124(5) C1A .036(2) .020(2) .024(2) -.0090(17) .0041(17) -.0103(17) C11A .033(2) .021(2) .027(2) -.0110(17) .0073(17) -.0137(17) C12A .031(2) .027(2) .031(2) -.0149(18) .0096(18) -.0170(18) O12A .0305(15) .0248(15) .0379(17) -.0103(12) .0059(13) -.0083(13) C13A .033(2) .025(2) .034(2) -.0100(18) .0004(18) -.0100(19) C14A .032(2) .028(2) .036(2) -.0141(18) .0078(18) -.0144(19) C17A .039(3) .038(3) .047(3) -.017(2) .005(2) -.012(2) C18A .039(2) .046(3) .049(3) -.019(2) .012(2) -.030(2) C15A .038(2) .029(2) .038(2) -.0190(19) .0067(19) -.0127(19) C16A .043(2) .024(2) .027(2) -.0167(19) .0012(18) -.0111(18) O16A .0408(17) .0244(16) .0419(18) -.0133(14) .0025(14) -.0086(14) C21A .031(2) .0201(19) .027(2) -.0100(17) .0022(17) -.0098(17) C22A .031(2) .027(2) .036(2) -.0121(18) .0099(18) -.0162(19) O22A .0412(17) .0285(16) .0297(16) -.0141(13) .0032(13) -.0155(13) C23A .036(2) .026(2) .033(2) -.0124(18) .0047(19) -.0057(19) C24A .038(2) .036(2) .032(2) -.019(2) .0061(19) -.013(2) C27A .052(3) .055(3) .052(3) -.033(3) .013(2) -.003(3) C28A .049(3) .065(3) .042(3) -.032(3) .015(2) -.030(3) C25A .036(2) .037(2) .032(2) -.019(2) .0111(18) -.015(2) C26A .030(2) .031(2) .030(2) -.0127(19) .0045(18) -.0161(19) O26A .0307(17) .0360(19) .049(2) -.0043(14) .0091(14) -.0090(16) C31A .031(2) .028(2) .029(2) -.0154(18) .0050(17) -.0081(18) C32A .028(2) .028(2) .037(3) -.0108(18) .0067(19) -.0078(19) Cl3A .0489(7) .0276(6) .0539(8) -.0037(5) .0053(6) -.0153(5) C33A .030(2) .040(3) .041(3) -.014(2) .003(2) -.005(2) C34A .041(3) .050(3) .029(2) -.027(2) -.001(2) -.003(2) C35A .044(3) .045(3) .032(2) -.028(2) .012(2) -.017(2) C36A .030(2) .024(2) .032(2) -.0145(17) .0034(17) -.0097(18) Cl6A .0358(6) .0302(5) .0390(6) -.0129(4) .0081(4) -.0201(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 C31 . 1.508(5) ? C1 C11 . 1.510(6) ? C1 C21 . 1.546(6) ? C1 H1 . 1.0000 ? C11 C12 . 1.337(6) ? C11 C16 . 1.437(6) ? C12 O12 . 1.349(5) y C12 C13 . 1.501(6) ? O12 C22 . 1.460(5) y C13 C14 . 1.532(6) ? C13 H13C . .9900 ? C13 H13D . .9900 ? C14 C15 . 1.519(6) ? C14 C18 . 1.529(7) ? C14 C17 . 1.533(7) ? C17 H17D . .9800 ? C17 H17E . .9800 ? C17 H17F . .9800 ? C18 H18D . .9800 ? C18 H18E . .9800 ? C18 H18F . .9800 ? C15 C16 . 1.494(6) ? C15 H15C . .9900 ? C15 H15D . .9900 ? C16 O16 . 1.232(5) y C21 C26 . 1.520(5) ? C21 C22 . 1.528(5) ? C21 H21 . 1.0000 ? C22 O22 . 1.392(4) y C22 C23 . 1.514(6) ? O22 H22 . .8400 ? C23 C24 . 1.548(5) ? C23 H23C . .9900 ? C23 H23D . .9900 ? C24 C28 . 1.524(6) ? C24 C27 . 1.527(6) ? C24 C25 . 1.534(6) ? C27 H27D . .9800 ? C27 H27E . .9800 ? C27 H27F . .9800 ? C28 H28D . .9800 ? C28 H28E . .9800 ? C28 H28F . .9800 ? C25 C26 . 1.496(6) ? C25 H25C . .9900 ? C25 H25D . .9900 ? C26 O26 . 1.207(5) y C31 C32 . 1.402(6) ? C31 C36 . 1.408(6) ? C32 C33 . 1.366(6) ? C32 Cl2 . 1.752(4) y C33 C34 . 1.388(6) ? C33 H33 . .9500 ? C34 C35 . 1.374(7) ? C34 H34 . .9500 ? C35 C36 . 1.379(6) ? C35 H35 . .9500 ? C36 Cl6 . 1.746(4) y C1A C11A . 1.517(5) ? C1A C31A . 1.523(5) ? C1A C21A . 1.539(5) ? C1A H1A . 1.0000 ? C11A C12A . 1.360(6) ? C11A C16A . 1.435(6) ? C12A O12A . 1.350(5) y C12A C13A . 1.485(6) ? O12A C22A . 1.451(5) y C13A C14A . 1.523(6) ? C13A H13A . .9900 ? C13A H13B . .9900 ? C14A C17A . 1.518(6) ? C14A C18A . 1.528(6) ? C14A C15A . 1.547(6) ? C17A H17A . .9800 ? C17A H17B . .9800 ? C17A H17C . .9800 ? C18A H18A . .9800 ? C18A H18B . .9800 ? C18A H18C . .9800 ? C15A C16A . 1.499(6) ? C15A H15A . .9900 ? C15A H15B . .9900 ? C16A O16A . 1.242(5) y C21A C22A . 1.522(6) ? C21A C26A . 1.521(5) ? C21A H21A . 1.0000 ? C22A O22A . 1.393(5) y C22A C23A . 1.516(6) ? O22A H22A . .8400 ? C23A C24A . 1.529(6) ? C23A H23A . .9900 ? C23A H23B . .9900 ? C24A C25A . 1.534(6) ? C24A C28A . 1.536(6) ? C24A C27A . 1.542(6) ? C27A H27A . .9800 ? C27A H27B . .9800 ? C27A H27C . .9800 ? C28A H28A . .9800 ? C28A H28B . .9800 ? C28A H28C . .9800 ? C25A C26A . 1.500(6) ? C25A H25A . .9900 ? C25A H25B . .9900 ? C26A O26A . 1.209(5) y C31A C32A . 1.402(6) ? C31A C36A . 1.409(5) ? C32A C33A . 1.371(6) ? C32A Cl3A . 1.750(4) y C33A C34A . 1.391(6) ? C33A H33A . .9500 ? C34A C35A . 1.376(6) ? C34A H34A . .9500 ? C35A C36A . 1.377(6) ? C35A H35A . .9500 ? C36A Cl6A . 1.742(4) y