#------------------------------------------------------------------------------ #$Date: 2020-01-14 16:52:43 +0200 (Tue, 14 Jan 2020) $ #$Revision: 246814 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/70/1557038.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_1557038 loop_ _publ_author_name 'Eklund, Ann-Marie' 'Forsblom, Ingrid' 'Berg, Jan-Eric' 'Damberg, Charlotta' 'Wahlberg, Inger' _publ_section_title ; Tobacco Chemistry. 83. Four New Cyclized Cembranoids from Tobacco ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 1254 _journal_page_last 1262 _journal_paper_doi 10.3891/acta.chem.scand.52-1254 _journal_volume 52 _journal_year 1998 _chemical_formula_sum 'C20 H32 O4' _chemical_formula_weight 336.47 _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 9.3134(4) _cell_length_b 11.3699(14) _cell_length_c 17.7933(11) _cell_volume 1884.2(3) _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _exptl_absorpt_coefficient_mu 0.610 _exptl_crystal_density_diffrn 1.19 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_number_parameters 230 _refine_ls_number_reflns 1705 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_gt 0.054 _refine_ls_wR_factor_ref 0.057 _cod_data_source_file Acta-Chem-Scand-1998-52-1254-1.cif _cod_data_source_block 1 _cod_database_code 1557038 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uiso -0.1520(2) -0.2791(2) -0.03590(10) 1.000 0.0407(6) . . . . O2 O Uiso 0.0894(3) -0.2744(2) 0.10880(10) 1.000 0.0571(8) . . . . O3 O Uiso -0.3152(2) -0.4774(2) 0.18230(10) 1.000 0.0379(6) . . . . O4 O Uiso -0.4092(2) -0.3438(2) 0.09490(10) 1.000 0.0353(6) . . . . C1 C Uiso -0.4524(3) -0.5458(2) 0.0449(2) 1.000 0.0415(8) . . . . C2 C Uiso -0.3661(3) -0.4305(2) 0.03950(10) 1.000 0.0323(7) . . . . C3 C Uiso -0.1996(3) -0.4500(2) 0.0405(2) 1.000 0.0328(7) . . . . C4 C Uiso -0.1133(3) -0.4020(2) -0.0269(2) 1.000 0.0359(8) . . . . C5 C Uiso 0.0406(3) -0.4111(3) 0.0022(2) 1.000 0.0389(8) . . . . C6 C Uiso 0.0347(3) -0.3871(3) 0.0874(2) 1.000 0.0414(9) . . . . C7 C Uiso -0.1260(3) -0.3889(2) 0.1061(2) 1.000 0.0341(8) . . . . C8 C Uiso -0.1670(3) -0.4351(3) 0.1854(2) 1.000 0.0376(8) . . . . C9 C Uiso -0.1783(4) -0.3311(3) 0.2393(2) 1.000 0.0498(10) . . . . C10 C Uiso -0.3259(4) -0.2788(3) 0.2185(2) 1.000 0.0543(11) . . . . C11 C Uiso -0.4027(3) -0.3771(3) 0.1747(2) 1.000 0.0411(8) . . . . C12 C Uiso -0.5542(3) -0.4091(3) 0.1960(2) 1.000 0.0486(10) . . . . C13 C Uiso -0.6076(4) -0.5227(3) 0.1632(2) 1.000 0.0553(11) . . . . C14 C Uiso -0.6026(3) -0.5303(3) 0.0780(2) 1.000 0.0490(10) . . . . C15 C Uiso -0.4565(4) -0.6067(3) -0.0333(2) 1.000 0.0599(11) . . . . C16 C Uiso -0.5629(5) -0.5489(5) -0.0881(2) 1.000 0.0787(16) . . . . C17 C Uiso -0.4870(6) -0.7378(4) -0.0270(3) 1.000 0.096(2) . . . . C18 C Uiso -0.1345(4) -0.4644(3) -0.1014(2) 1.000 0.0520(10) . . . . C19 C Uiso -0.0792(4) -0.5390(3) 0.2137(2) 1.000 0.0499(10) . . . . C20 C Uiso -0.6373(5) -0.3386(5) 0.2373(3) 1.000 0.0780(16) . . . . 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O3 C11 106.5(2) . . . yes C2 O4 C11 118.0(2) . . . yes C2 C1 C14 113.8(2) . . . no C2 C1 C15 109.6(2) . . . no C14 C1 C15 112.0(3) . . . no C11 C12 C13 114.9(3) . . . no C11 C12 C20 122.5(3) . . . no C13 C12 C20 122.6(3) . . . no O4 C2 C1 113.0(2) . . . yes O4 C2 C3 111.2(2) . . . yes C1 C2 C3 113.3(2) . . . no C2 C3 C4 117.2(2) . . . no C2 C3 C7 113.0(2) . . . no C4 C3 C7 101.5(2) . . . no O1 C4 C3 107.3(2) . . . yes O1 C4 C5 109.6(2) . . . yes O1 C4 C18 108.8(3) . . . yes C3 C4 C5 101.6(3) . . . no C3 C4 C18 116.5(2) . . . no C5 C4 C18 112.8(3) . . . no C4 C5 C6 106.7(2) . . . no O2 C6 C5 114.1(3) . . . yes O2 C6 C7 107.6(2) . . . yes C5 C6 C7 104.2(2) . . . no C3 C7 C6 106.2(3) . . . no C3 C7 C8 115.6(2) . . . no C6 C7 C8 116.2(3) . . . no O3 C8 C7 108.0(2) . . . yes O3 C8 C9 102.3(2) . . . yes O3 C8 C19 105.3(3) . . . yes C7 C8 C9 109.0(3) . . . no C7 C8 C19 115.5(3) . . . no C9 C8 C19 115.5(3) . . . no C8 C9 C10 102.1(3) . . . no C9 C10 C11 104.8(3) . . . no O3 C11 O4 109.0(2) . . . yes O3 C11 C12 108.8(3) . . . yes O3 C11 C10 105.7(2) . . . yes O4 C11 C12 105.5(2) . . . yes O4 C11 C10 108.7(3) . . . yes C12 C11 C10 118.9(3) . . . no C12 C13 C14 115.3(3) . . . no C1 C14 C13 114.8(3) . . . no C1 C15 C16 113.1(3) . . . no C1 C15 C17 112.0(3) . . . no C16 C15 C17 110.2(4) . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.452(3) . . yes O2 C6 1.431(4) . . yes O3 C8 1.463(3) . . yes O3 C11 1.408(4) . . yes O4 C2 1.451(3) . . yes O4 C11 1.471(4) . . yes C1 C2 1.541(3) . . no C1 C14 1.528(4) . . no C1 C15 1.555(5) . . no C12 C11 1.506(4) . . no C12 C13 1.502(5) . . no C12 C20 1.335(6) . . no C2 C3 1.567(4) . . no C3 C4 1.543(5) . . no C3 C7 1.522(5) . . no C4 C5 1.528(4) . . no C4 C18 1.516(5) . . no C5 C6 1.541(5) . . no C6 C7 1.533(4) . . no C7 C8 1.553(5) . . no C8 C9 1.526(5) . . no C8 C19 1.522(5) . . no C9 C10 1.543(5) . . no C10 C11 1.539(5) . . no C13 C14 1.519(5) . . no C15 C16 1.538(6) . . no C15 C17 1.522(6) . . no 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O3 C11 C10 -33.1(3) . . . . no C11 O3 C8 C9 44.6(3) . . . . no C11 O3 C8 C19 165.7(3) . . . . no C11 O3 C8 C7 -70.4(3) . . . . no C8 O3 C11 C12 -161.9(3) . . . . no C8 O3 C11 O4 83.6(3) . . . . no C2 O4 C11 O3 17.1(3) . . . . no C2 O4 C11 C10 131.9(3) . . . . no C2 O4 C11 C12 -99.5(3) . . . . no C11 O4 C2 C1 57.1(3) . . . . no C11 O4 C2 C3 -71.7(3) . . . . no C15 C1 C2 C3 -79.3(3) . . . . no C15 C1 C2 O4 153.0(2) . . . . no C14 C1 C2 O4 26.8(3) . . . . no C2 C1 C15 C17 158.0(3) . . . . no C14 C1 C15 C16 50.6(4) . . . . no C14 C1 C15 C17 -74.7(4) . . . . no C2 C1 C15 C16 -76.7(4) . . . . no C15 C1 C14 C13 154.7(3) . . . . no C14 C1 C2 C3 154.5(3) . . . . no C2 C1 C14 C13 -80.3(3) . . . . no C13 C12 C11 O3 -45.4(4) . . . . no C20 C12 C11 O4 -105.0(4) . . . . no C20 C12 C11 C10 17.3(5) . . . . no C13 C12 C11 O4 71.4(3) . . . . no C20 C12 C13 C14 119.2(4) . . . . no C13 C12 C11 C10 -166.4(3) . . . . no C11 C12 C13 C14 -57.1(4) . . . . no C20 C12 C11 O3 138.3(4) . . . . no C1 C2 C3 C4 122.6(2) . . . . no C1 C2 C3 C7 -119.9(2) . . . . no O4 C2 C3 C7 8.8(3) . . . . no O4 C2 C3 C4 -108.7(2) . . . . no C2 C3 C4 O1 52.4(3) . . . . no C7 C3 C4 O1 -71.2(3) . . . . no C2 C3 C4 C5 167.4(2) . . . . no C2 C3 C4 C18 -69.7(3) . . . . no C7 C3 C4 C5 43.9(2) . . . . no C7 C3 C4 C18 166.8(2) . . . . no C2 C3 C7 C6 -164.7(2) . . . . no C2 C3 C7 C8 64.8(3) . . . . no C4 C3 C7 C6 -38.4(3) . . . . no C4 C3 C7 C8 -168.9(2) . . . . no C3 C4 C5 C6 -33.9(3) . . . . no C18 C4 C5 C6 -159.4(3) . . . . no O1 C4 C5 C6 79.3(3) . . . . no C4 C5 C6 C7 10.7(3) . . . . no C4 C5 C6 O2 -106.4(3) . . . . no O2 C6 C7 C3 138.9(2) . . . . no C5 C6 C7 C8 147.5(3) . . . . no O2 C6 C7 C8 -91.0(3) . . . . no C5 C6 C7 C3 17.4(3) . . . . no C3 C7 C8 C9 -141.2(3) . . . . no C3 C7 C8 C19 86.9(3) . . . . no C6 C7 C8 O3 -156.2(2) . . . . no C6 C7 C8 C9 93.3(3) . . . . no C6 C7 C8 C19 -38.6(4) . . . . no C3 C7 C8 O3 -30.7(3) . . . . no C19 C8 C9 C10 -150.3(3) . . . . no O3 C8 C9 C10 -36.5(3) . . . . no C7 C8 C9 C10 77.7(3) . . . . no C8 C9 C10 C11 17.3(3) . . . . no C9 C10 C11 C12 131.2(3) . . . . no C9 C10 C11 O3 8.7(3) . . . . no C9 C10 C11 O4 -108.2(3) . . . . no C12 C13 C14 C1 73.5(4) . . . . no