#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012316.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_2012316 loop_ _publ_author_name 'Kennedy, Alan R.' 'Kerr, William J.' 'McLaughlin, Mark' 'Pauson, Peter L.' _publ_section_title ; Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes \a- and \b-cedrene ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1316 _journal_page_last 1318 _journal_paper_doi 10.1107/S0108270101013336 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C16 H22 O3' _chemical_formula_sum 'C16 H22 O3' _chemical_formula_weight 262.34 _chemical_name_systematic ; (3\b,3a\b,7\b)-(+-)-6,6-ethylenedioxy-3,8,8-trimethyl-2,3,3a,4,5,6,7,8- octahydro-3a,7-methanoazulen-2-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 107.469(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.0402(13) _cell_length_b 31.423(4) _cell_length_c 7.7111(13) _cell_measurement_reflns_used 21 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 10.72 _cell_measurement_theta_min 7.06 _cell_volume 1396.1(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1992)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full .971 _diffrn_measured_fraction_theta_max .971 _diffrn_measurement_device_type 'Rigaku AFC-7S' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .061 _diffrn_reflns_av_sigmaI/netI .090 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2977 _diffrn_reflns_theta_full 25.99 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_min 2.59 _diffrn_standards_decay_% 3.01 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .085 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description tabular _exptl_crystal_F_000 568 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .15 _refine_diff_density_max .18 _refine_diff_density_min -.15 _refine_ls_extinction_coef .017(2) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2721 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all .126 _refine_ls_R_factor_gt .048 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .142 _reflns_number_gt 1522 _reflns_number_total 2721 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1172.cif _cod_data_source_block IIIa _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012316 _cod_database_fobs_code 2012316 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' 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_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 '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 _geom_angle_publ_flag C15 O2 C12 108.3(3) ? C16 O3 C12 108.8(2) ? O1 C1 C2 127.5(2) ? O1 C1 C5 124.0(2) ? C2 C1 C5 108.22(18) y C3 C2 C1 108.7(2) ? C3 C2 H2 126 ? C1 C2 H2 126 ? C2 C3 C4 113.09(18) ? C2 C3 C7 135.2(2) y C4 C3 C7 110.71(17) ? C3 C4 C9 101.24(17) ? C3 C4 C5 103.21(16) ? C9 C4 C5 122.85(18) y C3 C4 C10 110.70(18) ? C9 C4 C10 107.54(18) ? C5 C4 C10 110.52(16) ? C6 C5 C1 108.28(17) ? C6 C5 C4 114.56(18) y C1 C5 C4 102.83(16) ? C6 C5 H5 110 ? C1 C5 H5 110 ? C4 C5 H5 110 ? C5 C6 H6A 110 ? C5 C6 H6B 110 ? H6A C6 H6B 110 ? C5 C6 H6C 110 ? H6A C6 H6C 110 ? H6B C6 H6C 110 ? C3 C7 C14 114.4(2) ? C3 C7 C13 107.07(17) ? C14 C7 C13 106.8(2) ? C3 C7 C8 101.06(16) ? C14 C7 C8 117.81(19) ? C13 C7 C8 109.3(2) ? C12 C8 C9 107.34(19) ? C12 C8 C7 115.6(2) ? C9 C8 C7 102.85(17) ? C12 C8 H8 110 ? C9 C8 H8 110 ? C7 C8 H8 110 ? C4 C9 C8 100.46(18) ? C4 C9 H9A 112 ? C8 C9 H9A 112 ? C4 C9 H9B 112 ? C8 C9 H9B 112 ? H9A C9 H9B 109.4 ? C11 C10 C4 112.96(18) ? C11 C10 H10A 109 ? C4 C10 H10A 109 ? C11 C10 H10B 109 ? C4 C10 H10B 109 ? H10A C10 H10B 107.8 ? C12 C11 C10 113.0(2) ? C12 C11 H11A 109 ? C10 C11 H11A 109 ? C12 C11 H11B 109 ? C10 C11 H11B 109 ? H11A C11 H11B 108 ? O3 C12 O2 105.36(19) ? O3 C12 C11 108.7(2) ? O2 C12 C11 110.1(2) ? O3 C12 C8 109.7(2) ? O2 C12 C8 110.98(19) ? C11 C12 C8 111.72(18) ? C7 C13 H13A 110 ? C7 C13 H13B 110 ? H13A C13 H13B 110 ? C7 C13 H13C 110 ? H13A C13 H13C 110 ? H13B C13 H13C 110 ? C7 C14 H14A 110 ? C7 C14 H14B 110 ? H14A C14 H14B 110 ? C7 C14 H14C 110 ? H14A C14 H14C 110 ? H14B C14 H14C 110 ? O2 C15 C16 107.3(3) ? O2 C15 H15A 110 ? C16 C15 H15A 110 ? O2 C15 H15B 110 ? C16 C15 H15B 110 ? H15A C15 H15B 108.5 ? O3 C16 C15 103.8(3) ? O3 C16 H16A 111 ? C15 C16 H16A 111 ? O3 C16 H16B 111 ? C15 C16 H16B 111 ? H16A C16 H16B 109 ? 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 ? 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 _geom_torsion_publ_flag O1 C1 C2 C3 -179.2(2) ? C5 C1 C2 C3 6.5(2) y C1 C2 C3 C4 7.0(3) y C1 C2 C3 C7 -160.0(2) ? C2 C3 C4 C9 -145.19(19) ? C7 C3 C4 C9 25.0(2) y C2 C3 C4 C5 -17.3(2) y C7 C3 C4 C5 152.94(16) ? C2 C3 C4 C10 101.0(2) ? C7 C3 C4 C10 -88.8(2) ? O1 C1 C5 C6 -69.3(3) ? C2 C1 C5 C6 105.2(2) ? O1 C1 C5 C4 169.1(2) ? C2 C1 C5 C4 -16.5(2) y C3 C4 C5 C6 -98.0(2) ? C9 C4 C5 C6 14.9(3) ? C10 C4 C5 C6 143.6(2) ? C3 C4 C5 C1 19.22(19) y C9 C4 C5 C1 132.2(2) ? C10 C4 C5 C1 -99.2(2) ? C2 C3 C7 C14 -61.0(3) ? C4 C3 C7 C14 131.8(2) ? C2 C3 C7 C13 57.0(3) ? C4 C3 C7 C13 -110.2(2) ? C2 C3 C7 C8 171.3(2) ? C4 C3 C7 C8 4.2(2) y C3 C7 C8 C12 84.9(2) ? C14 C7 C8 C12 -40.5(3) ? C13 C7 C8 C12 -162.46(19) ? C3 C7 C8 C9 -31.8(2) y C14 C7 C8 C9 -157.1(2) ? C13 C7 C8 C9 80.9(2) ? C3 C4 C9 C8 -43.9(2) y C5 C4 C9 C8 -157.83(18) ? C10 C4 C9 C8 72.2(2) ? C12 C8 C9 C4 -74.5(2) ? C7 C8 C9 C4 47.9(2) y C3 C4 C10 C11 51.4(3) ? C9 C4 C10 C11 -58.3(3) ? C5 C4 C10 C11 165.16(19) ? C4 C10 C11 C12 42.2(3) ? C16 O3 C12 O2 24.0(3) ? C16 O3 C12 C11 141.9(3) ? C16 O3 C12 C8 -95.6(3) ? C15 O2 C12 O3 -11.8(3) ? C15 O2 C12 C11 -128.9(3) ? C15 O2 C12 C8 106.9(3) ? C10 C11 C12 O3 77.6(3) ? C10 C11 C12 O2 -167.5(2) ? C10 C11 C12 C8 -43.7(3) ? C9 C8 C12 O3 -59.0(2) ? C7 C8 C12 O3 -173.09(17) ? C9 C8 C12 O2 -175.06(19) ? C7 C8 C12 O2 70.9(2) ? C9 C8 C12 C11 61.7(3) ? C7 C8 C12 C11 -52.4(3) ? C12 O2 C15 C16 -3.5(4) ? C12 O3 C16 C15 -25.6(4) ? O2 C15 C16 O3 17.9(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11277018