#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013375.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_2013375 loop_ _publ_author_name 'Sauer, Anne M.' 'Fronczek, Frank R.' 'Zhu, Betty C. R.' 'Crowe, William E.' 'Henderson, Gregg' 'Laine, Roger A.' _publ_section_title ; The sesquiterpenoid nootkatone and the absolute configuration of a dibromo derivative ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o254 _journal_page_last o256 _journal_paper_doi 10.1107/S010827010300684X _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C15 H22 O' _chemical_formula_moiety 'C15 H22 O' _chemical_formula_sum 'C15 H22 O' _chemical_formula_weight 218.33 _chemical_melting_point 310.0(10) _chemical_name_common nootkatone _chemical_name_systematic ? _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 96.09(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.903(2) _cell_length_b 9.495(4) _cell_length_c 11.630(6) _cell_measurement_reflns_used 1493 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.5 _cell_volume 648.2(5) _computing_cell_refinement 'DENZO and SCALEPACK' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)' _diffrn_measurement_method '\w scans with \k offsets' _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 0.023 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7526 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.7 _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'needle fragment' _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.16 _refine_diff_density_min -0.15 _refine_ls_extinction_coef 0.041(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1577 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.068 _refine_ls_R_factor_gt 0.041 _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^)+(0.0459P)^2^+0.0440P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.085 _refine_ls_wR_factor_ref 0.098 _reflns_number_gt 1202 _reflns_number_total 1577 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sq1013.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '309-311K' was changed to '310.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '309-311K' was changed to '310.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2013375 _cod_database_fobs_code 2013375 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -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 O1 0.9245(3) 0.4298(2) 0.40302(15) 0.0544(5) Uani d . 1 . . O C1 0.8374(4) 0.3090(3) 0.56883(19) 0.0324(5) Uani d . 1 . . C H1 0.9146 0.2268 0.5475 0.039 Uiso calc R 1 . . H C2 0.8218(4) 0.4282(3) 0.4894(2) 0.0379(6) Uani d . 1 . . C C3 0.6720(4) 0.5467(3) 0.5196(2) 0.0393(6) Uani d . 1 . . C H3A 0.5118 0.5248 0.4912 0.047 Uiso calc R 1 . . H H3B 0.7157 0.6337 0.4806 0.047 Uiso calc R 1 . . H C4 0.6917(4) 0.5713(2) 0.65075(19) 0.0317(6) Uani d . 1 . . C H4 0.8555 0.5923 0.6758 0.038 Uiso calc R 1 . . H C5 0.6313(3) 0.4369(3) 0.71613(18) 0.0274(5) Uani d . 1 . . C C6 0.7166(4) 0.4560(2) 0.84551(18) 0.0287(5) Uani d . 1 . . C H6A 0.8755 0.4908 0.8514 0.034 Uiso calc R 1 . . H H6B 0.6231 0.5299 0.8777 0.034 Uiso calc R 1 . . H C7 0.7101(4) 0.3238(2) 0.92099(19) 0.0280(5) Uani d . 1 . . C H7 0.5486 0.2903 0.9148 0.034 Uiso calc R 1 . . H C8 0.8507(4) 0.2093(3) 0.8705(2) 0.0343(6) Uani d . 1 . . C H8A 0.8446 0.1222 0.9169 0.041 Uiso calc R 1 . . H H8B 1.0117 0.2398 0.8744 0.041 Uiso calc R 1 . . H C9 0.7605(4) 0.1786(3) 0.7443(2) 0.0352(6) Uani d . 1 . . C H9A 0.8611 0.1087 0.7122 0.042 Uiso calc R 1 . . H H9B 0.6065 0.1367 0.7419 0.042 Uiso calc R 1 . . H C10 0.7490(3) 0.3088(2) 0.67038(18) 0.0283(5) Uani d . 1 . . C C11 0.7807(4) 0.3577(2) 1.04696(19) 0.0328(6) Uani d . 1 . . C C12 0.6291(4) 0.4579(3) 1.1030(2) 0.0431(7) Uani d . 1 . . C H12A 0.6755 0.4612 1.1864 0.065 Uiso calc R 1 . . H H12B 0.4709 0.4257 1.0892 0.065 Uiso calc R 1 . . H H12C 0.6421 0.5522 1.0700 0.065 Uiso calc R 1 . . H C13 0.9638(4) 0.3046(3) 1.1070(2) 0.0452(7) Uani d . 1 . . C H13A 0.9998 0.3298 1.1859 0.054 Uiso calc R 1 . . H H13B 1.0593 0.2412 1.0712 0.054 Uiso calc R 1 . . H C14 0.3711(4) 0.4100(3) 0.7018(2) 0.0397(6) Uani d . 1 . . C H14A 0.3148 0.4110 0.6194 0.060 Uiso calc R 1 . . H H14B 0.2944 0.4839 0.7420 0.060 Uiso calc R 1 . . H H14C 0.3394 0.3181 0.7349 0.060 Uiso calc R 1 . . H C15 0.5564(5) 0.7019(3) 0.6779(2) 0.0473(7) Uani d . 1 . . C H15A 0.6193 0.7846 0.6422 0.071 Uiso calc R 1 . . H H15B 0.5665 0.7152 0.7619 0.071 Uiso calc R 1 . . H H15C 0.3965 0.6897 0.6471 0.071 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 0.0656(12) 0.0614(13) 0.0393(10) -0.0189(11) 0.0202(9) -0.0027(10) C1 0.0315(11) 0.0327(12) 0.0330(12) -0.0024(10) 0.0037(10) -0.0046(11) C2 0.0368(12) 0.0485(16) 0.0287(11) -0.0164(12) 0.0044(10) -0.0046(12) C3 0.0409(13) 0.0428(15) 0.0327(13) -0.0061(12) -0.0042(11) 0.0093(11) C4 0.0324(11) 0.0326(14) 0.0290(12) -0.0024(10) -0.0018(10) 0.0046(10) C5 0.0242(10) 0.0287(11) 0.0289(11) -0.0007(9) 0.0020(9) 0.0016(10) C6 0.0312(11) 0.0260(12) 0.0287(11) 0.0003(9) 0.0025(9) 0.0006(10) C7 0.0284(11) 0.0259(12) 0.0298(11) -0.0007(9) 0.0031(9) 0.0002(10) C8 0.0432(13) 0.0256(12) 0.0347(13) 0.0026(10) 0.0064(11) 0.0022(10) C9 0.0459(14) 0.0257(13) 0.0349(13) 0.0003(11) 0.0086(11) -0.0030(10) C10 0.0233(10) 0.0300(12) 0.0312(12) -0.0035(9) 0.0004(9) -0.0002(10) C11 0.0402(14) 0.0270(12) 0.0319(12) -0.0009(10) 0.0076(11) 0.0019(10) C12 0.0556(16) 0.0426(16) 0.0324(13) 0.0069(13) 0.0110(11) -0.0009(12) C13 0.0531(15) 0.0436(15) 0.0371(13) 0.0117(13) -0.0038(12) 0.0007(13) C14 0.0264(11) 0.0484(17) 0.0443(14) -0.0025(11) 0.0031(10) -0.0025(12) C15 0.0597(17) 0.0369(14) 0.0429(15) 0.0118(13) -0.0052(13) 0.0048(13) 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 C10 C1 C2 123.7(2) C10 C1 H1 118.2 C2 C1 H1 118.2 O1 C2 C1 121.7(2) O1 C2 C3 122.5(2) C1 C2 C3 115.8(2) C2 C3 C4 111.27(18) C2 C3 H3A 109.4 C4 C3 H3A 109.4 C2 C3 H3B 109.4 C4 C3 H3B 109.4 H3A C3 H3B 108.0 C15 C4 C3 110.07(19) C15 C4 C5 114.6(2) C3 C4 C5 111.48(19) C15 C4 H4 106.8 C3 C4 H4 106.8 C5 C4 H4 106.8 C10 C5 C6 108.66(17) C10 C5 C4 110.44(16) C6 C5 C4 108.28(18) C10 C5 C14 108.32(19) C6 C5 C14 109.93(17) C4 C5 C14 111.17(19) C7 C6 C5 115.81(18) C7 C6 H6A 108.3 C5 C6 H6A 108.3 C7 C6 H6B 108.3 C5 C6 H6B 108.3 H6A C6 H6B 107.4 C11 C7 C8 114.82(17) C11 C7 C6 110.97(18) C8 C7 C6 108.41(18) C11 C7 H7 107.4 C8 C7 H7 107.4 C6 C7 H7 107.4 C7 C8 C9 110.89(18) C7 C8 H8A 109.5 C9 C8 H8A 109.5 C7 C8 H8B 109.5 C9 C8 H8B 109.5 H8A C8 H8B 108.1 C10 C9 C8 112.37(19) C10 C9 H9A 109.1 C8 C9 H9A 109.1 C10 C9 H9B 109.1 C8 C9 H9B 109.1 H9A C9 H9B 107.9 C1 C10 C9 120.4(2) C1 C10 C5 122.8(2) C9 C10 C5 116.82(19) C13 C11 C12 120.2(2) C13 C11 C7 123.7(2) C12 C11 C7 116.05(19) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C11 C13 H13A 120.0 C11 C13 H13B 120.0 H13A C13 H13B 120.0 C5 C14 H14A 109.5 C5 C14 H14B 109.5 H14A C14 H14B 109.5 C5 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C4 C15 H15A 109.5 C4 C15 H15B 109.5 H15A C15 H15B 109.5 C4 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 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 . 1.228(3) y C1 C10 . 1.341(3) y C1 C2 . 1.457(4) y C1 H1 . 0.9500 ? C2 C3 . 1.496(4) ? C3 C4 . 1.536(3) ? C3 H3A . 0.9900 ? C3 H3B . 0.9900 ? C4 C15 . 1.526(4) ? C4 C5 . 1.546(3) ? C4 H4 . 1.0000 ? C5 C10 . 1.524(3) ? C5 C6 . 1.546(3) ? C5 C14 . 1.549(3) ? C6 C7 . 1.535(3) ? C6 H6A . 0.9900 ? C6 H6B . 0.9900 ? C7 C11 . 1.515(3) ? C7 C8 . 1.523(3) ? C7 H7 . 1.0000 ? C8 C9 . 1.534(3) ? C8 H8A . 0.9900 ? C8 H8B . 0.9900 ? C9 C10 . 1.504(3) ? C9 H9A . 0.9900 ? C9 H9B . 0.9900 ? C11 C13 . 1.323(3) y C11 C12 . 1.501(3) y C12 H12A . 0.9800 ? C12 H12B . 0.9800 ? C12 H12C . 0.9800 ? C13 H13A . 0.9500 ? C13 H13B . 0.9500 ? C14 H14A . 0.9800 ? C14 H14B . 0.9800 ? C14 H14C . 0.9800 ? C15 H15A . 0.9800 ? C15 H15B . 0.9800 ? C15 H15C . 0.9800 ? 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 C10 C1 C2 O1 172.4(2) ? C10 C1 C2 C3 -8.1(3) y O1 C2 C3 C4 -142.6(2) ? C1 C2 C3 C4 37.9(3) y C2 C3 C4 C15 174.2(2) ? C2 C3 C4 C5 -57.5(3) y C15 C4 C5 C10 171.74(19) ? C3 C4 C5 C10 45.9(2) y C15 C4 C5 C6 -69.4(2) ? C3 C4 C5 C6 164.77(18) ? C15 C4 C5 C14 51.5(3) ? C3 C4 C5 C14 -74.4(2) ? C10 C5 C6 C7 -49.6(2) y C4 C5 C6 C7 -169.61(18) ? C14 C5 C6 C7 68.8(3) ? C5 C6 C7 C11 -175.80(18) ? C5 C6 C7 C8 57.2(2) y C11 C7 C8 C9 177.82(19) ? C6 C7 C8 C9 -57.5(2) y C7 C8 C9 C10 55.0(3) y C2 C1 C10 C9 176.45(19) ? C2 C1 C10 C5 -2.9(3) y C8 C9 C10 C1 130.8(2) ? C8 C9 C10 C5 -49.8(3) y C6 C5 C10 C1 -135.4(2) ? C4 C5 C10 C1 -16.7(3) y C14 C5 C10 C1 105.2(2) ? C6 C5 C10 C9 45.3(2) y C4 C5 C10 C9 163.92(18) ? C14 C5 C10 C9 -74.1(2) ? C8 C7 C11 C13 6.8(3) ? C6 C7 C11 C13 -116.5(3) ? C8 C7 C11 C12 -173.2(2) ? C6 C7 C11 C12 63.4(2) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 1064812