#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008964.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2008964 loop_ _publ_author_name 'Bats, Jan W.' '\"Ohlinger, Stefan H.' 'Mulzer, Johann' _publ_section_title ;(+-)-(3'a\a,3'b\a,6'a\a,7'a\a)- and (+-)-(3'a\a,3'b\b,6'a\b,7'a\a)-2,3,3a,3b,4,5,6,6a,7,7a-decahydro-5,5-dimethylspiro[1,3-dioxane-2,5'-pentaleno[2,1-b]furan]-2'-one ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900111 _journal_paper_doi 10.1107/S0108270199098807 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C15 H22 O4' _chemical_formula_weight 266.33 _chemical_melting_point 358.0(10) _chemical_name_systematic ; (+-)-(3'a\a,3'b\a,6'a\a,7'a\a)-octahydro-5,5-dimethyl-spiro[1,3-dioxane- 2,5'(2'H)pentaleno[2,1-b]furan]-2'-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 88.370(11) _cell_angle_beta 86.483(7) _cell_angle_gamma 70.162(11) _cell_formula_units_Z 2 _cell_length_a 5.6779(10) _cell_length_b 6.3017(11) _cell_length_c 20.480(3) _cell_measurement_reflns_used 186 _cell_measurement_temperature 134(2) _cell_measurement_theta_max 23 _cell_measurement_theta_min 3 _cell_volume 688.0(2) _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_publication_material 'CIF in SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 134(2) _diffrn_measured_fraction_theta_full 0.846 _diffrn_measured_fraction_theta_max 0.846 _diffrn_measurement_device_type 'Siemens SMART' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 11957 _diffrn_reflns_theta_full 31.98 _diffrn_reflns_theta_max 30.6 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_time 540 _diffrn_standards_number 209 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_type 'numerical (Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.424 _refine_diff_density_min -0.217 _refine_ls_extinction_coef 0.019(7) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.557 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 4038 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.557 _refine_ls_R_factor_all 0.045 _refine_ls_R_factor_gt 0.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.125 _reflns_number_gt 3582 _reflns_number_total 4038 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0163.cif _cod_data_source_block I _cod_original_cell_volume 687.98(19) _cod_original_sg_symbol_H-M ' P -1' _cod_database_code 2008964 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O3 0.61349(11) 0.34963(10) 0.70213(3) 0.01822(15) Uani d . 1 . . O O4 0.73237(11) 0.65651(10) 0.66612(3) 0.01993(15) Uani d . 1 . . O O1 0.35795(11) 0.66046(11) 0.90795(3) 0.02242(16) Uani d . 1 . . O C12 0.93013(16) 0.29285(16) 0.61165(4) 0.01990(18) Uani d . 1 . . C C9 0.64785(14) 0.55149(14) 0.72087(4) 0.01522(17) Uani d . 1 . . C C10 0.39794(14) 0.71640(15) 0.74632(4) 0.01813(18) Uani d . 1 . . C C7 0.73411(14) 0.76408(14) 0.80838(4) 0.01686(17) Uani d . 1 . . C C11 0.83738(16) 0.19124(15) 0.67249(4) 0.01944(18) Uani d . 1 . . C C6 0.46926(14) 0.89541(14) 0.78180(4) 0.01763(18) Uani d . 1 . . C C8 0.81423(14) 0.52473(15) 0.77922(4) 0.01761(18) Uani d . 1 . . C O2 0.55222(16) 0.30200(13) 0.93613(3) 0.03348(19) Uani d . 1 . . O C13 0.95950(17) 0.51212(16) 0.63356(4) 0.02159(19) Uani d . 1 . . C C4 0.41960(15) 0.86867(15) 0.90052(4) 0.01952(18) Uani d . 1 . . C C3 0.70387(14) 0.78402(14) 0.88450(4) 0.01828(18) Uani d . 1 . . C C5 0.29863(15) 1.00315(15) 0.84195(4) 0.02048(19) Uani d . 1 . . C C1 0.56371(18) 0.48610(16) 0.92408(4) 0.0229(2) Uani d . 1 . . C C15 1.18409(19) 0.12882(19) 0.58659(5) 0.0295(2) Uani d . 1 . . C C2 0.78730(17) 0.56475(16) 0.92379(4) 0.02267(19) Uani d . 1 . . C C14 0.73848(19) 0.3416(2) 0.55886(5) 0.0298(2) Uani d . 1 . . C H10B 0.327(2) 0.627(2) 0.7773(6) 0.024(3) Uiso d . 1 . . H H13B 1.102(2) 0.4811(19) 0.6627(6) 0.023(3) Uiso d . 1 . . H H8B 0.772(2) 0.416(2) 0.8091(6) 0.026(3) Uiso d . 1 . . H H4 0.372(2) 0.952(2) 0.9436(6) 0.024(3) Uiso d . 1 . . H H7 0.855(2) 0.8359(18) 0.7906(5) 0.016(2) Uiso d . 1 . . H H6 0.479(2) 1.0136(19) 0.7501(6) 0.019(3) Uiso d . 1 . . H H3 0.779(2) 0.892(2) 0.8988(6) 0.029(3) Uiso d . 1 . . H H8A 0.997(2) 0.464(2) 0.7678(6) 0.028(3) Uiso d . 1 . . H H11B 0.977(2) 0.144(2) 0.7064(6) 0.032(3) Uiso d . 1 . . H H11A 0.788(2) 0.064(2) 0.6613(6) 0.020(3) Uiso d . 1 . . H H10A 0.285(2) 0.772(2) 0.7112(6) 0.029(3) Uiso d . 1 . . H H2B 0.814(2) 0.597(2) 0.9702(7) 0.033(3) Uiso d . 1 . . H H5B 0.123(2) 1.005(2) 0.8376(7) 0.031(3) Uiso d . 1 . . H H5A 0.294(2) 1.161(2) 0.8477(6) 0.029(3) Uiso d . 1 . . H H15A 1.242(3) 0.195(2) 0.5455(7) 0.039(3) Uiso d . 1 . . H H2A 0.941(2) 0.447(2) 0.9076(6) 0.034(3) Uiso d . 1 . . H H14C 0.576(3) 0.442(2) 0.5744(7) 0.040(4) Uiso d . 1 . . H H13A 0.990(2) 0.596(2) 0.5949(7) 0.031(3) Uiso d . 1 . . H H14B 0.711(3) 0.209(2) 0.5470(7) 0.037(3) Uiso d . 1 . . H H14A 0.797(3) 0.411(3) 0.5199(9) 0.061(5) Uiso d . 1 . . H H15C 1.318(3) 0.101(2) 0.6192(7) 0.041(4) Uiso d . 1 . . H H15B 1.159(3) -0.020(3) 0.5766(8) 0.056(4) Uiso d . 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 O3 0.0178(3) 0.0170(3) 0.0207(3) -0.0076(2) 0.0036(2) -0.0036(2) O4 0.0241(3) 0.0173(3) 0.0177(3) -0.0069(2) 0.0027(2) 0.0021(2) O1 0.0225(3) 0.0234(3) 0.0233(3) -0.0107(3) 0.0019(2) -0.0008(3) C12 0.0197(4) 0.0235(4) 0.0170(4) -0.0083(3) 0.0021(3) -0.0034(3) C9 0.0156(3) 0.0147(4) 0.0157(4) -0.0058(3) 0.0000(3) 0.0002(3) C10 0.0134(3) 0.0180(4) 0.0212(4) -0.0027(3) -0.0021(3) -0.0017(3) C7 0.0139(3) 0.0176(4) 0.0188(4) -0.0050(3) 0.0001(3) -0.0013(3) C11 0.0202(4) 0.0159(4) 0.0208(4) -0.0048(3) 0.0035(3) -0.0024(3) C6 0.0154(3) 0.0151(4) 0.0206(4) -0.0031(3) -0.0008(3) 0.0004(3) C8 0.0151(3) 0.0184(4) 0.0167(4) -0.0020(3) -0.0015(3) -0.0012(3) O2 0.0562(5) 0.0231(4) 0.0231(4) -0.0168(3) 0.0031(3) -0.0009(3) C13 0.0235(4) 0.0243(4) 0.0191(4) -0.0118(3) 0.0052(3) -0.0017(3) C4 0.0183(4) 0.0190(4) 0.0208(4) -0.0059(3) 0.0021(3) -0.0041(3) C3 0.0157(3) 0.0195(4) 0.0196(4) -0.0056(3) -0.0007(3) -0.0041(3) C5 0.0165(4) 0.0171(4) 0.0248(4) -0.0017(3) 0.0000(3) -0.0028(3) C1 0.0322(4) 0.0219(4) 0.0138(4) -0.0085(4) 0.0013(3) -0.0023(3) C15 0.0259(4) 0.0313(5) 0.0290(5) -0.0081(4) 0.0097(4) -0.0076(4) C2 0.0236(4) 0.0227(4) 0.0183(4) -0.0029(3) -0.0035(3) -0.0017(3) C14 0.0314(5) 0.0424(6) 0.0182(4) -0.0151(4) -0.0032(3) -0.0027(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 O3 C11 112.61(6) C9 O4 C13 113.39(6) C1 O1 C4 109.96(7) C15 C12 C13 109.98(7) C15 C12 C11 109.10(8) C13 C12 C11 106.31(7) C15 C12 C14 110.85(8) C13 C12 C14 110.36(8) C11 C12 C14 110.13(8) O3 C9 O4 110.89(6) O3 C9 C10 109.11(6) O4 C9 C10 107.13(7) O3 C9 C8 114.46(7) O4 C9 C8 111.82(6) C10 C9 C8 102.85(6) C9 C10 C6 104.00(6) C8 C7 C3 117.38(7) C8 C7 C6 105.77(6) C3 C7 C6 106.61(6) O3 C11 C12 111.14(7) C10 C6 C5 115.88(7) C10 C6 C7 104.73(7) C5 C6 C7 105.99(7) C9 C8 C7 104.33(6) O4 C13 C12 111.25(7) O1 C4 C5 110.62(7) O1 C4 C3 103.80(7) C5 C4 C3 106.89(7) C2 C3 C4 101.49(7) C2 C3 C7 116.96(7) C4 C3 C7 105.05(6) C4 C5 C6 106.18(7) O2 C1 O1 121.14(9) O2 C1 C2 129.18(9) O1 C1 C2 109.69(8) C1 C2 C3 103.31(7) 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 O3 C9 . 1.4174(10) ? O3 C11 . 1.4350(10) ? O4 C9 . 1.4258(10) ? O4 C13 . 1.4381(11) ? O1 C1 . 1.3553(11) ? O1 C4 . 1.4701(11) ? C12 C15 . 1.5293(13) ? C12 C13 . 1.5295(13) ? C12 C11 . 1.5307(13) ? C12 C14 . 1.5317(12) ? C9 C10 . 1.5180(11) ? C9 C8 . 1.5388(11) ? C10 C6 . 1.5353(12) ? C7 C8 . 1.5462(12) ? C7 C3 . 1.5618(12) ? C7 C6 . 1.5725(11) ? C6 C5 . 1.5400(12) ? O2 C1 . 1.2017(12) ? C4 C5 . 1.5089(13) ? C4 C3 . 1.5356(11) ? C3 C2 . 1.5233(13) ? C1 C2 . 1.5111(14) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C11 O3 C9 O4 57.48(8) C11 O3 C9 C10 175.25(6) C11 O3 C9 C8 -70.16(8) C13 O4 C9 O3 -56.47(9) C13 O4 C9 C10 -175.44(6) C13 O4 C9 C8 72.59(8) O3 C9 C10 C6 164.97(7) O4 C9 C10 C6 -74.92(8) C8 C9 C10 C6 43.06(8) C9 O3 C11 C12 -58.76(9) C15 C12 C11 O3 173.45(7) C13 C12 C11 O3 54.89(9) C14 C12 C11 O3 -64.67(10) C9 C10 C6 C5 -147.19(7) C9 C10 C6 C7 -30.83(8) C8 C7 C6 C10 6.99(9) C3 C7 C6 C10 -118.66(7) C8 C7 C6 C5 130.00(7) C3 C7 C6 C5 4.35(9) O3 C9 C8 C7 -156.50(6) O4 C9 C8 C7 76.34(8) C10 C9 C8 C7 -38.30(8) C3 C7 C8 C9 137.76(7) C6 C7 C8 C9 19.03(8) C9 O4 C13 C12 56.35(9) C15 C12 C13 O4 -171.56(7) C11 C12 C13 O4 -53.58(9) C14 C12 C13 O4 65.83(9) C1 O1 C4 C5 138.45(7) C1 O1 C4 C3 24.11(9) O1 C4 C3 C2 -33.34(8) C5 C4 C3 C2 -150.31(7) O1 C4 C3 C7 88.91(8) C5 C4 C3 C7 -28.06(9) C8 C7 C3 C2 7.45(10) C6 C7 C3 C2 125.73(8) C8 C7 C3 C4 -104.15(8) C6 C7 C3 C4 14.14(9) O1 C4 C5 C6 -81.12(8) C3 C4 C5 C6 31.25(9) C10 C6 C5 C4 94.00(9) C7 C6 C5 C4 -21.65(9) C4 O1 C1 O2 175.80(8) C4 O1 C1 C2 -4.11(9) O2 C1 C2 C3 162.41(9) O1 C1 C2 C3 -17.69(9) C4 C3 C2 C1 30.63(8) C7 C3 C2 C1 -82.98(8) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4421810