#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011511.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_2011511 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1356 _journal_page_last 1358 _publ_section_title ; 4-Ethynyl-4-hydroxycyclohexan-1-one and 4-ethynyl-4-hydroxy-2,3,5,6-tetramethylcyclohexa-2,5-dien-1-one ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Bilton, Clair' 'Howard, Judith A. K.' 'Madhavi, N. N. Laxmi' 'Desiraju, Gautam R.' 'Allen, Frank H.' _chemical_formula_sum 'C12 H14 O2' _chemical_formula_weight 190.23 _symmetry_cell_setting 'monoclinic' 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 9.020(2) _cell_length_b 14.010(3) _cell_length_c 16.612(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.56(3) _cell_angle_gamma 90.00 _cell_volume 2095.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _exptl_crystal_density_diffrn 1.206 _diffrn_ambient_temperature 150 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 .4469(3) .18776(17) .29582(14) .0412(6) Uani d . 1 . . C H1 .447(3) .214(2) .3473(19) .077(9) Uiso d . 1 . . H C2 .4521(2) .15847(14) .22992(12) .0315(5) Uani d . 1 . . C C3 .4614(2) .12292(12) .14593(11) .0245(4) Uani d . 1 . . C O1 .45510(16) .20655(9) .09553(9) .0315(3) Uani d . 1 . . O H1A .470(3) .190(2) .0491(18) .062(9) Uiso d . 1 . . H C4 .3264(2) .06088(14) .12465(11) .0275(4) Uani d . 1 . . C C5 .1791(3) .10929(19) .13290(16) .0393(5) Uani d . 1 . . C H5A .115(3) .096(2) .0844(18) .067(9) Uiso d . 1 . . H H5B .126(3) .085(2) .180(2) .083(10) Uiso d . 1 . . H H5C .190(3) .179(2) .1393(17) .066(8) Uiso d . 1 . . H C6 .3409(2) -.02932(14) .09933(11) .0277(4) Uani d . 1 . . C C7 .2113(3) -.09396(18) .07707(16) .0472(6) Uani d . 1 . . C H7A .2235 -.1531 .1059 .094(11) Uiso calc R 1 . . H H7B .2069 -.1062 .0201 .103(12) Uiso calc R 1 . . H H7C .1209 -.0637 .0910 .114(13) Uiso calc R 1 . . H C8 .4884(2) -.07056(13) .09038(11) .0264(4) Uani d . 1 . . C O2 .50047(17) -.15168(9) .06234(8) .0347(4) Uani d . 1 . . O C9 .6232(2) -.01494(13) .11358(11) .0267(4) Uani d . 1 . . C C10 .7680(3) -.06559(19) .10501(17) .0414(6) Uani d . 1 . . C H10A .780(4) -.083(2) .050(2) .087(10) Uiso d . 1 . . H H10B .845(4) -.034(2) .1294(19) .080(10) Uiso d . 1 . . H H10C .765(4) -.130(3) .128(2) .097(12) Uiso d . 1 . . H C11 .6119(2) .07511(13) .13995(11) .0267(4) Uani d . 1 . . C C12 .7428(2) .13775(16) .16262(15) .0417(6) Uani d . 1 . . C H12A .7087 .1972 .1835 .101(12) Uiso calc R 1 . . H H12B .7973 .1497 .1158 .143(17) Uiso calc R 1 . . H H12C .8061 .1065 .2031 .136(16) Uiso calc R 1 . . H C21 -.0034(2) .27725(15) .27480(13) .0341(5) Uani d . 1 . . C H21 -.007(3) .2317(17) .3176(15) .049(7) Uiso d . 1 . . H C22 -.0059(2) .33843(13) .22580(11) .0262(4) Uani d . 1 . . C C23 -.0118(2) .41234(12) .16210(11) .0233(4) Uani d . 1 . . C O21 .00239(16) .50329(9) .20260(8) .0297(3) Uani d . 1 . . O H21A .013(3) .544(2) .1624(17) .063(8) Uiso d . 1 . . H C24 -.1634(2) .40601(13) .11764(11) .0249(4) Uani d . 1 . . C C25 -.2928(3) .42295(18) .16894(15) .0359(5) Uani d . 1 . . C H25A -.347(3) .478(2) .1522(19) .077(9) Uiso d . 1 . . H H25B -.364(4) .367(2) .160(2) .091(11) Uiso d . 1 . . H H25C -.263(3) .428(2) .222(2) .072(9) Uiso d . 1 . . H C26 -.1790(2) .38688(12) .03851(11) .0254(4) Uani d . 1 . . C C27 -.3273(2) .37967(17) -.00778(14) .0387(5) Uani d . 1 . . C H27A -.3825 .4374 -.0009 .134(16) Uiso calc R 1 . . H H27B -.3816 .3266 .0120 .17(2) Uiso calc R 1 . . H H27C -.3126 .3705 -.0640 .157(18) Uiso calc R 1 . . H C28 -.0462(2) .37392(12) -.00783(11) .0250(4) Uani d . 1 . . C O22 -.06202(17) .36239(9) -.08191(8) .0338(4) Uani d . 1 . . O C29 .1033(2) .37620(12) .03273(11) .0252(4) Uani d . 1 . . C C30 .2294(3) .35622(17) -.02003(14) .0350(5) Uani d . 1 . . C H30A .229(3) .291(2) -.0441(19) .087(10) Uiso d . 1 . . H H30B .322(4) .359(2) .008(2) .076(10) Uiso d . 1 . . H H30C .225(3) .395(2) -.0673(18) .065(8) Uiso d . 1 . . H C31 .1215(2) .39679(12) .11152(11) .0236(4) Uani d . 1 . . C C32 .2695(2) .40597(16) .15749(13) .0338(5) Uani d . 1 . . C H32A .3022 .4711 .1560 .122(14) Uiso calc R 1 . . H H32B .3405 .3657 .1334 .138(16) Uiso calc R 1 . . H H32C .2602 .3870 .2125 .150(17) 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 .0584(15) .0385(13) .0272(11) -.0011(11) .0055(11) -.0050(9) C2 .0390(12) .0254(10) .0301(11) .0007(9) .0033(9) .0004(8) C3 .0316(10) .0197(9) .0224(9) .0021(8) .0024(8) .0010(7) O1 .0456(9) .0230(7) .0262(8) .0056(6) .0050(7) .0029(6) C4 .0291(10) .0324(10) .0213(9) .0004(8) .0038(8) .0014(8) C5 .0288(12) .0474(15) .0424(14) .0064(10) .0074(10) -.0049(11) C6 .0310(10) .0301(10) .0223(9) -.0051(8) .0038(8) .0013(8) C7 .0486(14) .0454(14) .0484(15) -.0196(12) .0100(12) -.0075(12) C8 .0415(11) .0212(9) .0166(8) .0003(8) .0035(8) .0045(7) O2 .0567(9) .0217(7) .0263(7) .0019(6) .0064(7) -.0008(6) C9 .0314(10) .0282(10) .0203(9) .0060(8) .0003(8) .0034(7) C10 .0382(13) .0413(14) .0439(14) .0159(11) -.0052(11) -.0045(11) C11 .0303(10) .0265(10) .0229(9) .0017(8) -.0011(8) .0021(7) C12 .0330(12) .0379(13) .0533(15) -.0053(10) -.0034(11) -.0078(11) C21 .0465(13) .0291(11) .0265(10) -.0066(9) .0007(9) .0036(9) C22 .0301(10) .0273(10) .0212(9) -.0018(8) .0015(8) -.0027(8) C23 .0295(10) .0203(9) .0202(9) -.0010(7) .0029(8) -.0017(7) O21 .0433(8) .0217(7) .0247(7) -.0025(6) .0061(6) -.0038(6) C24 .0267(10) .0213(9) .0270(10) .0018(7) .0045(8) .0022(7) C25 .0324(12) .0406(13) .0357(12) .0024(10) .0096(10) .0012(10) C26 .0289(10) .0194(9) .0277(10) -.0020(7) -.0013(8) .0007(7) C27 .0346(12) .0428(13) .0376(13) -.0048(10) -.0056(10) .0015(10) C28 .0397(11) .0128(8) .0227(9) -.0003(7) .0037(8) -.0005(7) O22 .0515(9) .0278(7) .0222(7) -.0012(6) .0020(6) -.0036(6) C29 .0331(10) .0166(9) .0265(10) .0034(7) .0072(8) .0014(7) C30 .0386(13) .0350(12) .0328(12) .0093(10) .0140(10) .0011(10) C31 .0282(10) .0171(9) .0255(9) .0007(7) .0027(8) .0033(7) C32 .0280(11) .0363(12) .0369(12) .0008(9) .0001(9) .0014(9) 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 C2 . 1.173(3) yes C1 H1 . .93(3) yes C2 C3 . 1.489(3) no C3 O1 . 1.439(2) no C3 C4 . 1.520(3) no C3 C11 . 1.523(3) no O1 H1A . .82(3) yes C4 C6 . 1.341(3) no C4 C5 . 1.505(3) yes C5 H5A . .98(3) no C5 H5B . 1.00(3) no C5 H5C . .99(3) no C6 C8 . 1.467(3) no C6 C7 . 1.507(3) no C7 H7A . .9600 no C7 H7B . .9600 no C7 H7C . .9600 no C8 O2 . 1.236(2) yes C8 C9 . 1.475(3) no C9 C11 . 1.341(3) no C9 C10 . 1.501(3) no C10 H10A . .96(4) no C10 H10B . .90(3) no C10 H10C . .98(4) no C11 C12 . 1.500(3) no C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no C21 C22 . 1.181(3) yes C21 H21 . .96(3) yes C22 C23 . 1.479(3) no C23 O21 . 1.443(2) no C23 C24 . 1.516(3) no C23 C31 . 1.524(3) no O21 H21A . .89(3) yes C24 C26 . 1.340(3) no C24 C25 . 1.507(3) yes C25 H25A . .95(3) no C25 H25B . 1.02(4) no C25 H25C . .91(3) no C26 C28 . 1.475(3) no C26 C27 . 1.504(3) no C27 H27A . .9600 no C27 H27B . .9600 no C27 H27C . .9600 no C28 O22 . 1.241(2) yes C28 C29 . 1.470(3) no C29 C31 . 1.340(3) no C29 C30 . 1.504(3) no C30 H30A . 1.00(3) no C30 H30B . .93(3) no C30 H30C . .96(3) no C31 C32 . 1.502(3) no C32 H32A . .9600 no C32 H32B . .9600 no C32 H32C . .9600 no