#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/87/1518775.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1518775 loop_ _publ_author_name 'Gao, Chun' 'Han, Li' 'Zheng, Dan' 'Jin, Hongwei' 'Gai, Chunyan' 'Wang, Jianbin' 'Zhang, Hao' 'Zhang, Liangren' 'Fu, Hongzheng' _publ_section_title ; Dimeric Abietane Diterpenoids and Sesquiterpenoid Lactones from Teucrium viscidum. ; _journal_issue 4 _journal_name_full 'Journal of natural products' _journal_page_first 630 _journal_page_last 638 _journal_paper_doi 10.1021/np500746n _journal_volume 78 _journal_year 2015 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H28 O4' _chemical_formula_sum 'C20 H28 O4' _chemical_formula_weight 332.42 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.734(7) _cell_length_b 12.344(4) _cell_length_c 13.282(5) _cell_measurement_temperature 295(2) _cell_volume 1759.9(14) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_molecular_graphics ORTEPII(Johnson,1976)andPLUTON(Spek,1990) _computing_publication_material 'SHELXL97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'MicroMax 002+' _diffrn_measurement_method \f\k _diffrn_radiation_monochromator confocal _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 27220 _diffrn_reflns_theta_full 72.23 _diffrn_reflns_theta_max 72.23 _diffrn_reflns_theta_min 4.89 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.689 _exptl_absorpt_correction_T_max 0.7422 _exptl_absorpt_correction_T_min 0.6706 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.46 _refine_diff_density_max 0.230 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(15) _refine_ls_extinction_coef 0.0118(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 3406 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0319 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.0862 _reflns_number_gt 3331 _reflns_number_total 3406 _reflns_threshold_expression >2sigma(I) _cod_data_source_file np500746n_si_002.cif _cod_data_source_block 5643 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas Adding full bibliography for 1518774--1518775.cif. ; _cod_original_sg_symbol_H-M P212121 _cod_database_code 1518775 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 1.03759(11) 0.99302(8) 0.95403(7) 0.0456(3) Uani 1 1 d . H1 H 1.0578 1.0321 0.9068 0.068 Uiso 1 1 calc R O2 O 0.89839(9) 0.62234(8) 0.70382(8) 0.0470(2) Uani 1 1 d . O3 O 0.68663(11) 0.98005(7) 0.74831(9) 0.0511(3) Uani 1 1 d . H3 H 0.6366 1.0220 0.7227 0.077 Uiso 1 1 calc R O4 O 0.48137(11) 0.95478(8) 0.64778(7) 0.0471(3) Uani 1 1 d . H4 H 0.4744 0.9630 0.5868 0.071 Uiso 1 1 calc R C1 C 0.90009(12) 0.89327(10) 0.84251(9) 0.0349(3) Uani 1 1 d . H1A H 0.9269 0.9344 0.7842 0.042 Uiso 1 1 calc R H1B H 0.8319 0.9325 0.8736 0.042 Uiso 1 1 calc R C2 C 1.00751(12) 0.88686(10) 0.91695(9) 0.0350(3) Uani 1 1 d . H2 H 1.0806 0.8553 0.8839 0.042 Uiso 1 1 calc R C3 C 0.97105(13) 0.81808(11) 1.00688(9) 0.0385(3) Uani 1 1 d . H3A H 0.8999 0.8510 1.0399 0.046 Uiso 1 1 calc R H3B H 1.0395 0.8172 1.0546 0.046 Uiso 1 1 calc R C4 C 0.93823(13) 0.70102(11) 0.97836(10) 0.0384(3) Uani 1 1 d . C5 C 0.83208(11) 0.70468(10) 0.89869(9) 0.0314(3) Uani 1 1 d . H5 H 0.7591 0.7330 0.9344 0.038 Uiso 1 1 calc R C6 C 0.79283(13) 0.59180(10) 0.85967(10) 0.0389(3) Uani 1 1 d . H6A H 0.8560 0.5387 0.8768 0.047 Uiso 1 1 calc R H6B H 0.7150 0.5701 0.8909 0.047 Uiso 1 1 calc R C7 C 0.77706(12) 0.59715(10) 0.74631(10) 0.0386(3) Uani 1 1 d . H7 H 0.7474 0.5274 0.7206 0.046 Uiso 1 1 calc R C8 C 0.68815(13) 0.68527(10) 0.71790(10) 0.0359(3) Uani 1 1 d . C9 C 0.72849(11) 0.78717(9) 0.75105(9) 0.0312(2) Uani 1 1 d . C10 C 0.85226(11) 0.78253(10) 0.80728(9) 0.0310(3) Uani 1 1 d . C11 C 0.65552(13) 0.87582(10) 0.72336(9) 0.0349(3) Uani 1 1 d . C12 C 0.54723(13) 0.86098(10) 0.66705(9) 0.0347(3) Uani 1 1 d . C13 C 0.50557(13) 0.75904(11) 0.63619(9) 0.0370(3) Uani 1 1 d . C14 C 0.58035(13) 0.67086(11) 0.66259(10) 0.0389(3) Uani 1 1 d . H14 H 0.5573 0.6015 0.6427 0.047 Uiso 1 1 calc R C15 C 0.38463(14) 0.74868(12) 0.57755(11) 0.0457(3) Uani 1 1 d . H15 H 0.3843 0.8056 0.5261 0.055 Uiso 1 1 calc R C16 C 0.27206(16) 0.76757(19) 0.64557(17) 0.0712(5) Uani 1 1 d . H16A H 0.2666 0.7102 0.6941 0.107 Uiso 1 1 calc R H16B H 0.1976 0.7688 0.6055 0.107 Uiso 1 1 calc R H16C H 0.2812 0.8356 0.6798 0.107 Uiso 1 1 calc R C17 C 0.37130(17) 0.64039(14) 0.52341(13) 0.0569(4) Uani 1 1 d . H17A H 0.4438 0.6276 0.4828 0.085 Uiso 1 1 calc R H17B H 0.2987 0.6420 0.4812 0.085 Uiso 1 1 calc R H17C H 0.3630 0.5834 0.5721 0.085 Uiso 1 1 calc R C18 C 0.88594(17) 0.64419(14) 1.07220(12) 0.0551(4) Uani 1 1 d . H18A H 0.9482 0.6433 1.1241 0.083 Uiso 1 1 calc R H18B H 0.8632 0.5712 1.0554 0.083 Uiso 1 1 calc R H18C H 0.8138 0.6825 1.0957 0.083 Uiso 1 1 calc R C19 C 1.05683(15) 0.64023(13) 0.94624(14) 0.0535(4) Uani 1 1 d . H19A H 1.1000 0.6816 0.8960 0.080 Uiso 1 1 calc R H19B H 1.0345 0.5708 0.9190 0.080 Uiso 1 1 calc R H19C H 1.1099 0.6303 1.0037 0.080 Uiso 1 1 calc R C20 C 0.94163(13) 0.72906(11) 0.73159(10) 0.0398(3) Uani 1 1 d . H20A H 0.9478 0.7739 0.6718 0.048 Uiso 1 1 calc R H20B H 1.0240 0.7236 0.7612 0.048 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0671(7) 0.0332(5) 0.0365(4) 0.0009(4) -0.0046(4) -0.0188(4) O2 0.0481(5) 0.0390(5) 0.0540(5) -0.0148(4) 0.0046(4) 0.0074(4) O3 0.0694(7) 0.0245(4) 0.0595(6) -0.0053(4) -0.0230(5) 0.0056(4) O4 0.0629(6) 0.0355(5) 0.0429(5) -0.0009(4) -0.0106(5) 0.0180(4) C1 0.0445(7) 0.0269(5) 0.0332(6) 0.0028(4) -0.0011(5) -0.0058(5) C2 0.0388(6) 0.0290(6) 0.0373(6) -0.0024(5) -0.0009(5) -0.0078(5) C3 0.0461(8) 0.0337(6) 0.0357(6) 0.0034(5) -0.0061(5) -0.0070(5) C4 0.0433(7) 0.0314(6) 0.0405(6) 0.0068(5) -0.0085(5) -0.0052(5) C5 0.0318(6) 0.0273(6) 0.0351(6) 0.0024(5) 0.0006(4) -0.0017(4) C6 0.0404(7) 0.0269(6) 0.0496(7) 0.0033(5) -0.0075(5) -0.0034(5) C7 0.0404(7) 0.0255(6) 0.0499(7) -0.0069(5) -0.0066(5) 0.0035(5) C8 0.0427(7) 0.0280(6) 0.0372(6) -0.0033(5) -0.0051(5) 0.0032(5) C9 0.0366(6) 0.0258(5) 0.0311(5) -0.0010(4) -0.0009(4) 0.0009(4) C10 0.0361(6) 0.0258(6) 0.0313(5) 0.0000(4) 0.0008(4) -0.0013(4) C11 0.0463(7) 0.0265(6) 0.0318(5) -0.0025(5) -0.0020(5) 0.0038(5) C12 0.0424(7) 0.0299(6) 0.0320(5) 0.0001(4) -0.0017(5) 0.0075(5) C13 0.0417(7) 0.0355(6) 0.0337(6) 0.0004(5) -0.0046(5) 0.0014(5) C14 0.0462(8) 0.0279(6) 0.0426(6) -0.0036(5) -0.0077(5) 0.0008(5) C15 0.0479(8) 0.0431(7) 0.0461(7) 0.0066(6) -0.0124(6) -0.0001(6) C16 0.0474(10) 0.0834(14) 0.0827(13) -0.0040(11) -0.0036(8) 0.0062(9) C17 0.0664(10) 0.0531(9) 0.0511(8) 0.0011(7) -0.0213(7) -0.0099(8) C18 0.0668(10) 0.0510(9) 0.0476(8) 0.0202(7) -0.0148(7) -0.0169(8) C19 0.0458(8) 0.0368(7) 0.0778(10) 0.0025(7) -0.0169(7) 0.0035(6) C20 0.0408(7) 0.0404(7) 0.0381(6) -0.0048(5) 0.0049(5) -0.0006(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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 C2 O1 H1 109.5 C20 O2 C7 112.58(9) C11 O3 H3 109.5 C12 O4 H4 109.5 C2 C1 C10 113.94(10) C2 C1 H1A 108.8 C10 C1 H1A 108.8 C2 C1 H1B 108.8 C10 C1 H1B 108.8 H1A C1 H1B 107.7 O1 C2 C3 107.37(10) O1 C2 C1 110.22(11) C3 C2 C1 110.21(11) O1 C2 H2 109.7 C3 C2 H2 109.7 C1 C2 H2 109.7 C2 C3 C4 113.07(10) C2 C3 H3A 109.0 C4 C3 H3A 109.0 C2 C3 H3B 109.0 C4 C3 H3B 109.0 H3A C3 H3B 107.8 C3 C4 C18 108.27(12) C3 C4 C19 109.74(12) C18 C4 C19 107.73(13) C3 C4 C5 107.98(10) C18 C4 C5 107.31(11) C19 C4 C5 115.57(12) C6 C5 C4 113.68(10) C6 C5 C10 109.36(10) C4 C5 C10 116.40(10) C6 C5 H5 105.5 C4 C5 H5 105.5 C10 C5 H5 105.5 C7 C6 C5 108.91(10) C7 C6 H6A 109.9 C5 C6 H6A 109.9 C7 C6 H6B 109.9 C5 C6 H6B 109.9 H6A C6 H6B 108.3 O2 C7 C8 108.57(11) O2 C7 C6 107.15(11) C8 C7 C6 110.70(11) O2 C7 H7 110.1 C8 C7 H7 110.1 C6 C7 H7 110.1 C14 C8 C9 122.77(12) C14 C8 C7 125.08(12) C9 C8 C7 112.11(11) C11 C9 C8 116.61(11) C11 C9 C10 130.36(11) C8 C9 C10 112.91(10) C9 C10 C1 114.06(10) C9 C10 C20 103.85(10) C1 C10 C20 111.91(11) C9 C10 C5 106.42(10) C1 C10 C5 110.93(10) C20 C10 C5 109.28(10) O3 C11 C12 117.16(11) O3 C11 C9 122.42(12) C12 C11 C9 120.42(11) O4 C12 C11 114.59(12) O4 C12 C13 122.49(12) C11 C12 C13 122.87(11) C12 C13 C14 116.38(12) C12 C13 C15 119.99(12) C14 C13 C15 123.64(12) C8 C14 C13 120.94(12) C8 C14 H14 119.5 C13 C14 H14 119.5 C13 C15 C17 113.32(13) C13 C15 C16 111.10(13) C17 C15 C16 109.80(15) C13 C15 H15 107.5 C17 C15 H15 107.5 C16 C15 H15 107.5 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C15 C17 H17A 109.5 C15 C17 H17B 109.5 H17A C17 H17B 109.5 C15 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C4 C18 H18A 109.5 C4 C18 H18B 109.5 H18A C18 H18B 109.5 C4 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C4 C19 H19A 109.5 C4 C19 H19B 109.5 H19A C19 H19B 109.5 C4 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 O2 C20 C10 110.96(11) O2 C20 H20A 109.4 C10 C20 H20A 109.4 O2 C20 H20B 109.4 C10 C20 H20B 109.4 H20A C20 H20B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.4367(15) O1 H1 0.8200 O2 C20 1.4446(17) O2 C7 1.4530(19) O3 C11 1.3700(16) O3 H3 0.8200 O4 C12 1.3806(15) O4 H4 0.8200 C1 C2 1.5210(18) C1 C10 1.5335(17) C1 H1A 0.9700 C1 H1B 0.9700 C2 C3 1.5168(18) C2 H2 0.9800 C3 C4 1.5348(18) C3 H3A 0.9700 C3 H3B 0.9700 C4 C18 1.536(2) C4 C19 1.538(2) C4 C5 1.5556(18) C5 C6 1.5452(17) C5 C10 1.5636(16) C5 H5 0.9800 C6 C7 1.517(2) C6 H6A 0.9700 C6 H6B 0.9700 C7 C8 1.4955(18) C7 H7 0.9800 C8 C14 1.382(2) C8 C9 1.4012(17) C9 C11 1.3951(17) C9 C10 1.5252(18) C10 C20 1.5383(18) C11 C12 1.3943(19) C12 C13 1.3969(18) C13 C14 1.3972(18) C13 C15 1.519(2) C14 H14 0.9300 C15 C17 1.525(2) C15 C16 1.527(3) C15 H15 0.9800 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 H20A 0.9700 C20 H20B 0.9700 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 C10 C1 C2 O1 -173.89(10) C10 C1 C2 C3 -55.55(14) O1 C2 C3 C4 -179.09(11) C1 C2 C3 C4 60.83(15) C2 C3 C4 C18 -172.31(12) C2 C3 C4 C19 70.34(15) C2 C3 C4 C5 -56.43(15) C3 C4 C5 C6 177.71(11) C18 C4 C5 C6 -65.77(15) C19 C4 C5 C6 54.41(15) C3 C4 C5 C10 49.26(15) C18 C4 C5 C10 165.77(12) C19 C4 C5 C10 -74.04(15) C4 C5 C6 C7 -136.47(11) C10 C5 C6 C7 -4.50(14) C20 O2 C7 C8 53.87(14) C20 O2 C7 C6 -65.72(13) C5 C6 C7 O2 63.55(13) C5 C6 C7 C8 -54.67(15) O2 C7 C8 C14 120.06(14) C6 C7 C8 C14 -122.60(14) O2 C7 C8 C9 -57.88(14) C6 C7 C8 C9 59.47(15) C14 C8 C9 C11 -1.52(19) C7 C8 C9 C11 176.48(11) C14 C8 C9 C10 -177.92(12) C7 C8 C9 C10 0.08(15) C11 C9 C10 C1 3.00(17) C8 C9 C10 C1 178.77(10) C11 C9 C10 C20 -119.07(14) C8 C9 C10 C20 56.71(13) C11 C9 C10 C5 125.64(13) C8 C9 C10 C5 -58.58(13) C2 C1 C10 C9 167.64(10) C2 C1 C10 C20 -74.84(14) C2 C1 C10 C5 47.49(14) C6 C5 C10 C9 59.33(12) C4 C5 C10 C9 -170.15(10) C6 C5 C10 C1 -176.08(10) C4 C5 C10 C1 -45.55(14) C6 C5 C10 C20 -52.23(13) C4 C5 C10 C20 78.30(14) C8 C9 C11 O3 -178.00(13) C10 C9 C11 O3 -2.4(2) C8 C9 C11 C12 1.10(17) C10 C9 C11 C12 176.75(12) O3 C11 C12 O4 -3.05(17) C9 C11 C12 O4 177.81(11) O3 C11 C12 C13 179.59(12) C9 C11 C12 C13 0.44(19) O4 C12 C13 C14 -178.74(12) C11 C12 C13 C14 -1.58(19) O4 C12 C13 C15 1.06(19) C11 C12 C13 C15 178.22(12) C9 C8 C14 C13 0.4(2) C7 C8 C14 C13 -177.35(13) C12 C13 C14 C8 1.16(19) C15 C13 C14 C8 -178.63(13) C12 C13 C15 C17 162.94(13) C14 C13 C15 C17 -17.3(2) C12 C13 C15 C16 -72.89(18) C14 C13 C15 C16 106.90(17) C7 O2 C20 C10 5.49(15) C9 C10 C20 O2 -59.79(13) C1 C10 C20 O2 176.73(10) C5 C10 C20 O2 53.46(14)