data_2012316 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1316 _journal_page_last 1318 _publ_section_title ; Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes \a- and \b-cedrene ; loop_ _publ_author_name 'Kennedy, Alan R.' 'Kerr, William J.' 'McLaughlin, Mark' 'Pauson, Peter L.' _chemical_formula_moiety 'C16 H22 O3' _chemical_formula_sum 'C16 H22 O3' _chemical_formula_weight 262.34 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0402(13) _cell_length_b 31.423(4) _cell_length_c 7.7111(13) _cell_angle_alpha 90 _cell_angle_beta 107.469(15) _cell_angle_gamma 90 _cell_volume 1396.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _exptl_crystal_density_diffrn 1.248 _diffrn_ambient_temperature 295(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 .4059(3) -.01602(5) .7178(2) .0581(5) Uani d . 1 . . O O2 .2944(4) .21646(5) .7625(3) .0761(6) Uani d . 1 . . O O3 .1227(4) .19061(6) .9653(3) .0815(7) Uani d . 1 . . O C1 .3382(4) .02062(7) .7164(3) .0398(5) Uani d . 1 . . C C2 .3508(4) .05474(7) .5890(3) .0413(5) Uani d . 1 . . C H2 .4117 .0521 .4921 .050 Uiso calc R 1 . . H C3 .2608(3) .08994(6) .6353(3) .0334(5) Uani d . 1 . . C C4 .2031(4) .08565(6) .8116(3) .0338(5) Uani d . 1 . . C C5 .2010(4) .03721(6) .8395(3) .0373(5) Uani d . 1 . . C H5 .2807 .0300 .9665 .045 Uiso calc R 1 . . H C6 -.0401(4) .01703(7) .7789(4) .0539(7) Uani d . 1 . . C H6A -.1156 .0241 .6540 .081 Uiso calc R 1 . . H H6B -.1303 .0276 .8530 .081 Uiso calc R 1 . . H H6C -.0258 -.0133 .7917 .081 Uiso calc R 1 . . H C7 .1624(4) .13113(7) .5391(3) .0422(6) Uani d . 1 . . C C8 .0592(4) .15198(7) .6824(3) .0452(6) Uani d . 1 . . C H8 -.0763 .1694 .6212 .054 Uiso calc R 1 . . H C9 -.0155(4) .11313(7) .7733(3) .0466(6) Uani d . 1 . . C H9A -.0491 .1209 .8844 .056 Uiso calc R 1 . . H H9B -.1493 .0990 .6918 .056 Uiso calc R 1 . . H C10 .3924(4) .10675(7) .9690(3) .0453(6) Uani d . 1 . . C H10A .3417 .1068 1.0771 .054 Uiso calc R 1 . . H H10B .5332 .0899 .9952 .054 Uiso calc R 1 . . H C11 .4463(5) .15231(7) .9267(3) .0556(7) Uani d . 1 . . C H11A .5296 .1664 1.0392 .067 Uiso calc R 1 . . H H11B .5470 .1517 .8497 .067 Uiso calc R 1 . . H C12 .2313(5) .17780(7) .8331(3) .0541(7) Uani d . 1 . . C C13 -.0380(5) .11880(8) .3683(3) .0651(8) Uani d . 1 . . C H13A .0226 .1025 .2874 .098 Uiso calc R 1 . . H H13B -.1107 .1441 .3077 .098 Uiso calc R 1 . . H H13C -.1502 .1021 .4037 .098 Uiso calc R 1 . . H C14 .3359(5) .15733(8) .4728(4) .0634(8) Uani d . 1 . . C H14A .4644 .1655 .5750 .095 Uiso calc R 1 . . H H14B .2605 .1824 .4114 .095 Uiso calc R 1 . . H H14C .3913 .1405 .3904 .095 Uiso calc R 1 . . H C15 .1855(8) .25013(10) .8219(6) .1173(16) Uani d . 1 . . C H15A .0919 .2664 .7188 .141 Uiso calc R 1 . . H H15B .3003 .2690 .8995 .141 Uiso calc R 1 . . H C16 .0364(8) .23152(10) .9246(6) .1047(13) Uani d . 1 . . C H16A .0494 .2476 1.0346 .126 Uiso calc R 1 . . H H16B -.1249 .2309 .8509 .126 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 .0723(12) .0379(9) .0643(12) .0130(8) .0209(10) .0006(8) O2 .1065(16) .0297(9) .0880(14) -.0054(10) .0232(12) -.0001(9) O3 .1281(19) .0504(11) .0743(13) .0276(12) .0430(13) -.0070(10) C1 .0383(12) .0361(12) .0404(12) .0000(10) .0048(10) -.0029(9) C2 .0458(13) .0441(13) .0378(12) -.0002(10) .0183(11) -.0026(10) C3 .0332(11) .0343(11) .0314(11) -.0045(9) .0077(9) -.0011(8) C4 .0365(12) .0321(11) .0322(11) -.0005(9) .0092(9) -.0002(9) C5 .0403(13) .0347(11) .0336(11) -.0018(9) .0063(10) .0030(9) C6 .0526(16) .0475(14) .0625(16) -.0104(12) .0189(13) .0029(12) C7 .0503(14) .0355(12) .0387(12) -.0018(10) .0104(10) .0037(9) C8 .0410(13) .0379(12) .0535(14) .0111(10) .0090(11) .0061(10) C9 .0421(13) .0473(13) .0530(14) .0069(11) .0179(11) .0037(11) C10 .0527(14) .0402(12) .0371(12) .0031(10) .0047(11) -.0053(9) C11 .0612(17) .0396(13) .0524(14) -.0023(12) -.0034(12) -.0089(11) C12 .0733(18) .0336(12) .0555(16) .0061(12) .0195(14) -.0032(11) C13 .076(2) .0574(16) .0448(14) .0011(14) -.0082(14) .0067(12) C14 .080(2) .0524(15) .0622(17) -.0088(14) .0287(15) .0100(13) C15 .181(5) .0385(18) .131(4) .018(2) .046(3) .001(2) C16 .144(4) .058(2) .110(3) .041(2) .035(3) -.0116(19) 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 . 1.221(2) y O2 C15 . 1.394(4) ? O2 C12 . 1.429(3) ? O3 C16 . 1.387(3) ? O3 C12 . 1.426(3) ? C1 C2 . 1.471(3) y C1 C5 . 1.527(3) y C2 C3 . 1.328(3) y C2 H2 . .930 ? C3 C4 . 1.508(3) y C3 C7 . 1.521(3) y C4 C9 . 1.531(3) ? C4 C5 . 1.538(3) ? C4 C10 . 1.545(3) ? C5 C6 . 1.527(3) ? C5 H5 . .980 ? C6 H6A . .960 ? C6 H6B . .960 ? C6 H6C . .960 ? C7 C14 . 1.536(3) ? C7 C13 . 1.547(3) ? C7 C8 . 1.566(3) ? C8 C12 . 1.538(3) ? C8 C9 . 1.541(3) ? C8 H8 . .980 ? C9 H9A . .970 ? C9 H9B . .970 ? C10 C11 . 1.525(3) ? C10 H10A . .970 ? C10 H10B . .970 ? C11 C12 . 1.512(3) ? C11 H11A . .970 ? C11 H11B . .970 ? C13 H13A . .960 ? C13 H13B . .960 ? C13 H13C . .960 ? C14 H14A . .960 ? C14 H14B . .960 ? C14 H14C . .960 ? C15 C16 . 1.486(6) ? C15 H15A . .970 ? C15 H15B . .970 ? C16 H16A . .970 ? C16 H16B . .970 ?