data_2011328 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1173 _journal_page_last 1175 _publ_section_title ; (2R,3R,5R)-2-[(2R,3aS,6aR)-2,3,3a,4,5,6a-Hexahydrofuro[2,3-b]furan-2-yl]- 5-isopropenyl-2,3-dimethylcyclohexanone and (4aR,5S,7R)-5-isopropenyl-7,8,8-trimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalene -4a-carbonitrile ; loop_ _publ_author_name 'Ellis, Dianne D.' 'Spek, Anthony L.' _chemical_formula_moiety 'C17 H23 N O' _chemical_formula_sum 'C17 H23 N O' _chemical_formula_weight 257.36 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.3419(9) _cell_length_b 12.3902(10) _cell_length_c 14.4052(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1488.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.148 _diffrn_ambient_temperature 150(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 .0718(4) .2874(2) -.02667(17) .0422(8) Uani d . 1 . . O N1 -.0928(4) .6141(2) .1741(3) .0426(10) Uani d . 1 . . N C1 .2051(5) .3654(3) .0995(3) .0291(10) Uani d . 1 . . C H1 .3065 .3494 .0727 .035 Uiso calc R 1 . . H C2 .0615(5) .3249(3) .0515(2) .0278(9) Uani d . 1 . . C C3 -.0963(5) .3372(3) .0999(3) .0278(9) Uani d . 1 . . C H3A -.1658 .2748 .0848 .033 Uiso calc R 1 . . H H3B -.1502 .4035 .0775 .033 Uiso calc R 1 . . H C4 -.0739(5) .3439(3) .2040(2) .0245(9) Uani d . 1 . . C H4A -.0322 .2742 .2272 .029 Uiso calc R 1 . . H H4B -.1791 .3570 .2338 .029 Uiso calc R 1 . . H C5 .0430(4) .4350(3) .2313(2) .0225(9) Uani d . 1 . . C C6 .0728(4) .4289(3) .3377(2) .0274(9) Uani d . 1 . . C H6 .1159 .3549 .3494 .033 Uiso calc R 1 . . H C7 .2049(4) .5060(3) .3678(3) .0328(10) Uani d . 1 . . C H7A .2187 .5016 .4359 .039 Uiso calc R 1 . . H H7B .1736 .5809 .3520 .039 Uiso calc R 1 . . H C8 .3636(5) .4789(3) .3202(3) .0332(10) Uani d . 1 . . C H8 .4417 .5360 .3392 .040 Uiso calc R 1 . . H C9 .3499(4) .4849(3) .2131(3) .0262(9) Uani d . 1 . . C C10 .2034(4) .4232(3) .1781(3) .0235(9) Uani d . 1 . . C C11 .3324(5) .6045(3) .1839(3) .0399(11) Uani d . 1 . . C H11A .4317 .6434 .1981 .060 Uiso calc R 1 . . H H11B .2432 .6374 .2179 .060 Uiso calc R 1 . . H H11C .3113 .6086 .1170 .060 Uiso calc R 1 . . H C12 .5044(4) .4439(3) .1675(3) .0396(11) Uani d . 1 . . C H12A .5115 .3655 .1749 .059 Uiso calc R 1 . . H H12B .5971 .4781 .1972 .059 Uiso calc R 1 . . H H12C .5033 .4621 .1013 .059 Uiso calc R 1 . . H C13 .4303(5) .3714(3) .3559(3) .0483(12) Uani d . 1 . . C H13A .4245 .3699 .4238 .073 Uiso calc R 1 . . H H13B .5422 .3638 .3363 .073 Uiso calc R 1 . . H H13C .3669 .3118 .3304 .073 Uiso calc R 1 . . H C14 -.0777(5) .4374(4) .3966(3) .0425(11) Uani d . 1 . . C C15 -.1657(6) .5369(4) .4007(3) .0586(14) Uani d . 1 . . C H15A -.2609 .5273 .4397 .088 Uiso calc R 1 . . H H15B -.1987 .5579 .3380 .088 Uiso calc R 1 . . H H15C -.0976 .5935 .4273 .088 Uiso calc R 1 . . H C16 -.1212(6) .3492(4) .4495(3) .0579(14) Uani d . 1 . . C H16A -.2112 .3535 .4897 .070 Uiso calc R 1 . . H H16B -.0612 .2842 .4456 .070 Uiso calc R 1 . . H C17 -.0307(4) .5382(3) .2024(3) .0282(9) Uani d . 1 . . C 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 .0486(18) .0500(18) .0281(16) .0001(15) .0006(17) -.0145(14) N1 .034(2) .0274(18) .067(3) .0033(17) -.008(2) -.0054(19) C1 .027(2) .030(2) .030(2) .0013(19) .002(2) -.0022(18) C2 .039(2) .021(2) .023(2) .0038(19) .002(2) -.0001(16) C3 .029(2) .027(2) .027(2) .0020(19) -.004(2) -.0041(17) C4 .023(2) .0235(18) .027(2) -.0011(16) .002(2) -.0018(15) C5 .025(2) .0195(18) .0232(19) -.0019(16) .0015(18) -.0014(16) C6 .027(2) .033(2) .022(2) .0012(18) .001(2) -.0059(18) C7 .033(2) .036(2) .029(2) -.005(2) -.002(2) -.0086(18) C8 .029(2) .034(2) .036(2) -.0057(19) -.004(2) -.0072(19) C9 .019(2) .026(2) .033(2) .0001(16) .000(2) -.0027(17) C10 .024(2) .0182(19) .028(2) .0020(16) -.0033(19) .0037(17) C11 .036(2) .035(2) .049(3) -.008(2) -.003(2) .005(2) C12 .024(2) .046(2) .048(3) -.001(2) .002(2) -.008(2) C13 .035(2) .056(3) .054(3) .003(2) -.013(3) .013(2) C14 .036(3) .066(3) .025(2) -.013(2) -.001(2) -.017(2) C15 .048(3) .080(4) .048(3) .011(3) .009(3) -.025(3) C16 .058(3) .073(3) .043(3) -.015(3) .016(3) .003(3) C17 .024(2) .026(2) .034(2) .0033(18) -.001(2) -.0068(18) 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 C2 . 1.222(4) y N1 C17 . 1.148(4) y C1 C10 . 1.341(5) y C1 C2 . 1.471(5) ? C1 H1 . .9500 ? C2 C3 . 1.497(5) ? C3 C4 . 1.514(5) ? C3 H3A . .9900 ? C3 H3B . .9900 ? C4 C5 . 1.542(5) ? C4 H4A . .9900 ? C4 H4B . .9900 ? C5 C17 . 1.479(5) ? C5 C10 . 1.549(5) ? C5 C6 . 1.555(5) ? C6 C14 . 1.519(5) ? C6 C7 . 1.521(5) ? C6 H6 . 1.0000 ? C7 C8 . 1.528(5) ? C7 H7A . .9900 ? C7 H7B . .9900 ? C8 C13 . 1.532(5) ? C8 C9 . 1.548(6) ? C8 H8 . 1.0000 ? C9 C10 . 1.527(5) ? C9 C12 . 1.533(5) ? C9 C11 . 1.548(5) ? C11 H11A . .9800 ? C11 H11B . .9800 ? C11 H11C . .9800 ? C12 H12A . .9800 ? C12 H12B . .9800 ? C12 H12C . .9800 ? C13 H13A . .9800 ? C13 H13B . .9800 ? C13 H13C . .9800 ? C14 C16 . 1.381(6) y C14 C15 . 1.436(6) y C15 H15A . .9800 ? C15 H15B . .9800 ? C15 H15C . .9800 ? C16 H16A . .9500 ? C16 H16B . .9500 ?