#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012199.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_2012199 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1075 _journal_page_last 1078 _publ_section_title ; (-)-Dioxosantadienic acid: hydrogen-bonding patterns in a bicyclic sesquiterpenoid keto acid and its monohydrate ; _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 'Brunskill, Andrew P. J.' 'Lalancette, Roger A.' 'Thompson, Hugh W.' _chemical_name_common '(-)-dioxosantadienic acid' _chemical_formula_moiety 'C15 H18 O4' _chemical_formula_sum 'C15 H18 O4' _chemical_formula_weight 262.29 _chemical_melting_point 401 _symmetry_cell_setting 'Monoclinic' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6790(10) _cell_length_b 14.644(2) _cell_length_c 12.4610(10) _cell_angle_alpha 90 _cell_angle_beta 96.430(10) _cell_angle_gamma 90 _cell_volume 1392.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.251 _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 .7898(3) .17650(14) .54831(14) .0556(5) Uani d . 1 . . O O2 .6499(3) .50663(14) .37863(17) .0595(6) Uani d . 1 . . O O3 1.1114(3) .18792(17) .7325(2) .0743(7) Uani d . 1 . . O O4 1.0418(3) .04132(14) .7111(2) .0744(7) Uani d . 1 . . O C1 .7264(3) .23389(18) .60235(19) .0364(6) Uani d . 1 . . C C2 .7395(3) .22810(18) .72488(19) .0365(6) Uani d . 1 . . C C3 .5580(4) .2419(2) .7632(2) .0496(7) Uani d . 1 . . C C4 .4635(4) .3252(2) .7133(2) .0488(7) Uani d . 1 . . C C4A .4478(3) .32526(19) .5891(2) .0416(6) Uani d . 1 . . C C5 .3600(4) .4109(2) .5475(3) .0569(8) Uani d . 1 . . C C6 .4248(4) .4692(2) .4817(3) .0571(8) Uani d . 1 . . C C7 .5944(3) .45290(18) .4428(2) .0434(7) Uani d . 1 . . C C8 .6949(3) .37145(17) .4821(2) .0357(6) Uani d . 1 . . C C8A .6284(3) .31523(17) .55296(18) .0347(6) Uani d . 1 . . C C9 .8256(3) .13868(19) .7675(2) .0404(6) Uani d . 1 . . C C10 1.0060(4) .1279(2) .7333(2) .0483(7) Uani d . 1 . . C C11 .8439(4) .1329(2) .8909(2) .0611(8) Uani d . 1 . . C C12 .8687(4) .3588(2) .4404(2) .0530(7) Uani d . 1 . . C C13 .3371(4) .2434(2) .5421(3) .0591(8) Uani d . 1 . . C O1' .5317(3) .61527(15) .7730(2) .0705(7) Uani d . 1 . . O O2' .9029(3) .36362(14) 1.01065(18) .0609(6) Uani d . 1 . . O O3' .5089(3) .7646(2) .96756(18) .0878(9) Uani d . 1 . . O O4' .3300(3) .83035(15) .83896(16) .0555(5) Uani d . 1 . . O C1' .6819(3) .63031(19) .8086(2) .0428(6) Uani d . 1 . . C C2' .7574(3) .72503(19) .8259(2) .0386(6) Uani d . 1 . . C C3' .9197(3) .7333(2) .7649(2) .0434(6) Uani d . 1 . . C C4' 1.0505(3) .65698(18) .7949(2) .0433(7) Uani d . 1 . . C C4A' .9720(3) .56014(19) .7775(2) .0432(6) Uani d . 1 . . C C5' 1.1047(4) .4901(2) .8162(2) .0521(7) Uani d . 1 . . C C6' 1.0814(4) .4270(2) .8898(3) .0536(7) Uani d . 1 . . C C7' .9221(4) .42372(19) .9427(2) .0469(7) Uani d . 1 . . C C8' .7879(3) .49391(19) .9153(2) .0464(7) Uani d . 1 . . C C8A' .8109(3) .55516(19) .8370(2) .0418(6) Uani d . 1 . . C C9' .6167(3) .79821(18) .7985(2) .0414(6) Uani d . 1 . . C C10' .4820(4) .79310(19) .8773(2) .0461(7) Uani d . 1 . . C C11' .6913(4) .8960(2) .8029(3) .0616(9) Uani d . 1 . . C C12' .6320(4) .4947(2) .9785(3) .0706(10) Uani d . 1 . . C C13' .9183(4) .5435(2) .6550(2) .0639(9) Uani d . 1 . . C H4 1.1409 .0380 .6928 .095(14) Uiso calc R 1 . . H H2A .8144 .2784 .7541 .036(3) Uiso calc R 1 . . H H3A .4870 .1881 .7450 .050(3) Uiso calc R 1 . . H H3B .5714 .2482 .8412 .050(3) Uiso calc R 1 . . H H4A .5261 .3796 .7400 .050(3) Uiso calc R 1 . . H H4B .3470 .3277 .7362 .050(3) Uiso calc R 1 . . H H5A .2511 .4243 .5695 .060(4) Uiso calc R 1 . . H H6A .3616 .5214 .4598 .060(4) Uiso calc R 1 . . H H9A .7530 .0875 .7382 .036(3) Uiso calc R 1 . . H H11A .7297 .1334 .9153 .078(3) Uiso calc R 1 . . H H11B .9101 .1843 .9209 .078(3) Uiso calc R 1 . . H H11C .9034 .0774 .9139 .078(3) Uiso calc R 1 . . H H12A .8512 .3472 .3641 .078(3) Uiso calc R 1 . . H H12B .9287 .3080 .4765 .078(3) Uiso calc R 1 . . H H12C .9378 .4131 .4539 .078(3) Uiso calc R 1 . . H H13A .3914 .1874 .5684 .078(3) Uiso calc R 1 . . H H13B .3300 .2446 .4647 .078(3) Uiso calc R 1 . . H H13C .2214 .2473 .5640 .078(3) Uiso calc R 1 . . H H4' .2607 .8261 .8843 .13(2) Uiso calc R 1 . . H H2'A .7977 .7309 .9031 .036(3) Uiso calc R 1 . . H H3'A .8835 .7313 .6878 .050(3) Uiso calc R 1 . . H H3'B .9759 .7917 .7815 .050(3) Uiso calc R 1 . . H H4'A 1.0965 .6637 .8702 .050(3) Uiso calc R 1 . . H H4'B 1.1477 .6633 .7520 .050(3) Uiso calc R 1 . . H H5'A 1.2109 .4905 .7870 .060(4) Uiso calc R 1 . . H H6'A 1.1689 .3839 .9078 .060(4) Uiso calc R 1 . . H H9'A .5588 .7867 .7256 .036(3) Uiso calc R 1 . . H H11D .7670 .9035 .7472 .078(3) Uiso calc R 1 . . H H11E .7567 .9063 .8721 .078(3) Uiso calc R 1 . . H H11F .5967 .9391 .7922 .078(3) Uiso calc R 1 . . H H12D .5671 .4390 .9654 .078(3) Uiso calc R 1 . . H H12E .5582 .5457 .9562 .078(3) Uiso calc R 1 . . H H12F .6714 .4998 1.0541 .078(3) Uiso calc R 1 . . H H13D .8794 .4816 .6440 .078(3) Uiso calc R 1 . . H H13E 1.0172 .5543 .6160 .078(3) Uiso calc R 1 . . H H13F .8250 .5844 .6295 .078(3) 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 .0756(14) .0496(11) .0441(10) .0175(11) .0170(10) -.0033(10) O2 .0611(13) .0504(12) .0687(14) -.0048(11) .0140(11) .0161(11) O3 .0521(13) .0654(15) .1093(19) -.0083(12) .0258(13) -.0004(14) O4 .0680(15) .0514(14) .1101(18) .0126(12) .0373(14) .0023(13) C1 .0350(13) .0381(14) .0371(13) -.0021(12) .0085(11) -.0038(12) C2 .0404(13) .0338(13) .0359(13) .0017(12) .0071(11) -.0023(11) C3 .0509(16) .0618(19) .0381(14) .0046(15) .0138(13) .0023(14) C4 .0441(14) .0569(18) .0480(15) .0115(14) .0161(12) .0001(14) C4A .0345(13) .0445(15) .0467(15) .0003(13) .0083(11) .0040(13) C5 .0426(16) .067(2) .063(2) .0158(16) .0154(14) .0088(17) C6 .0551(18) .0481(18) .069(2) .0141(15) .0118(16) .0159(16) C7 .0460(15) .0407(16) .0431(15) -.0052(13) .0035(13) .0019(13) C8 .0360(13) .0361(14) .0351(14) -.0038(12) .0037(11) -.0036(11) C8A .0344(12) .0381(14) .0317(12) -.0013(12) .0042(11) -.0053(11) C9 .0421(14) .0377(14) .0424(14) .0007(13) .0087(11) .0023(12) C10 .0503(17) .0463(18) .0489(16) .0052(16) .0073(13) .0064(14) C11 .073(2) .064(2) .0481(16) .0116(18) .0119(15) .0129(15) C12 .0498(16) .0579(18) .0537(17) .0027(15) .0170(14) .0062(15) C13 .0437(16) .073(2) .0599(18) -.0155(17) .0012(14) .0043(17) O1' .0409(12) .0545(14) .1141(19) -.0060(10) -.0007(12) .0067(13) O2' .0563(12) .0522(13) .0760(15) .0043(10) .0163(11) .0176(11) O3' .0897(16) .121(2) .0585(15) .0478(16) .0336(13) .0365(14) O4' .0457(11) .0603(13) .0607(12) .0025(10) .0076(10) -.0045(11) C1' .0349(15) .0454(16) .0497(15) -.0049(13) .0118(12) .0017(13) C2' .0427(14) .0415(14) .0324(13) -.0025(12) .0071(11) .0010(11) C3' .0428(14) .0480(16) .0398(14) -.0081(14) .0063(12) .0034(13) C4' .0358(14) .0545(19) .0408(14) -.0068(13) .0101(11) .0002(13) C4A' .0424(14) .0461(16) .0423(15) -.0012(13) .0097(12) -.0062(13) C5' .0480(16) .0552(19) .0556(18) .0034(15) .0170(14) -.0057(15) C6' .0477(16) .0473(17) .0668(19) .0122(14) .0114(14) -.0011(16) C7' .0510(16) .0422(16) .0481(16) .0002(14) .0075(13) -.0026(14) C8' .0406(14) .0396(15) .0606(18) -.0053(13) .0128(13) -.0011(14) C8A' .0343(13) .0392(15) .0519(15) -.0057(12) .0049(12) -.0063(13) C9' .0478(15) .0398(15) .0368(13) .0013(13) .0055(12) .0053(12) C10' .0482(16) .0404(15) .0506(17) .0036(13) .0095(13) .0009(13) C11' .0593(19) .0450(17) .081(2) .0018(16) .0091(17) .0130(16) C12' .0597(19) .060(2) .097(3) .0141(18) .0331(18) .0298(19) C13' .078(2) .066(2) .0475(17) -.0016(18) .0066(16) -.0157(16) 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 C1 . 1.212(3) ? O2 C7 . 1.232(3) ? O3 C10 . 1.196(3) Y O4 C10 . 1.333(4) Y C1 C8A . 1.503(4) ? C1 C2 . 1.521(3) ? C2 C9 . 1.535(4) ? C2 C3 . 1.536(3) ? C3 C4 . 1.517(4) ? C4 C4A . 1.539(4) ? C4A C5 . 1.489(4) ? C4A C8A . 1.513(3) ? C4A C13 . 1.546(4) ? C5 C6 . 1.319(4) ? C6 C7 . 1.459(4) ? C7 C8 . 1.474(4) ? C8 C8A . 1.349(3) ? C8 C12 . 1.497(4) ? C9 C10 . 1.503(4) ? C9 C11 . 1.530(4) ? O1' C1' . 1.208(3) ? O2' C7' . 1.241(3) ? O3' C10' . 1.196(3) y O4' C10' . 1.328(3) y C1' C8A' . 1.496(4) ? C1' C2' . 1.510(4) ? C2' C9' . 1.533(4) ? C2' C3' . 1.535(3) ? C3' C4' . 1.520(4) ? C4' C4A' . 1.547(4) ? C4A' C5' . 1.488(4) ? C4A' C8A' . 1.514(4) ? C4A' C13' . 1.555(4) ? C5' C6' . 1.327(4) ? C6' C7' . 1.454(4) ? C7' C8' . 1.468(4) ? C8' C8A' . 1.351(4) ? C8' C12' . 1.505(4) ? C9' C10' . 1.506(4) ? C9' C11' . 1.541(4) ? O4 H4 . .8200 ? C2 H2A . .9800 ? C3 H3A . .9700 ? C3 H3B . .9700 ? C4 H4A . .9700 ? C4 H4B . .9700 ? C5 H5A . .9300 ? C6 H6A . .9300 ? C9 H9A . .9800 ? C11 H11A . .9600 ? C11 H11B . .9600 ? C11 H11C . .9600 ? C12 H12A . .9600 ? C12 H12B . .9600 ? C12 H12C . .9600 ? C13 H13A . .9600 ? C13 H13B . .9600 ? C13 H13C . .9600 ? O4' H4' . .8200 ? C2' H2'A . .9800 ? C3' H3'A . .9700 ? C3' H3'B . .9700 ? C4' H4'A . .9700 ? C4' H4'B . .9700 ? C5' H5'A . .9300 ? C6' H6'A . .9300 ? C9' H9'A . .9800 ? C11' H11D . .9600 ? C11' H11E . .9600 ? C11' H11F . .9600 ? C12' H12D . .9600 ? C12' H12E . .9600 ? C12' H12F . .9600 ? C13' H13D . .9600 ? C13' H13E . .9600 ? C13' H13F . .9600 ? _cod_database_code 2012199