#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/61/2006162.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_2006162 loop_ _publ_author_name 'Manr\'iquez, V.' 'Labb\'e, C.' 'Castillo, M.' 'Wittke, O.' _publ_contact_author ; Prof. Oscar Wittke Departamento de F\'isica Facultad de Ciencias F\'isicas y Matem\'aticas Universidad de Chile Casilla 487-3 Santiago, Chile ; _publ_section_title ; 1\a,5\a-Dihydroxymanoyl Oxide, a Novel Diterpene from Satureja gilliesii ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 624 _journal_page_last 626 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C20 H34 O3' _chemical_formula_weight 322.5 _chemical_melting_point .143E-141 _chemical_name_systematic ; 1\a,5\a-Dihydroxymanoyl oxide ; _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' _cell_angle_alpha 90.0 _cell_angle_beta 92.24(2) _cell_angle_gamma 90.0 _cell_formula_units_Z 2 _cell_length_a 8.467(2) _cell_length_b 11.154(2) _cell_length_c 9.654(2) _cell_measurement_reflns_used 19 _cell_measurement_temperature 295 _cell_measurement_theta_max 15 _cell_measurement_theta_min 7.5 _cell_volume 911.0(3) _computing_cell_refinement 'P3/P4-PC Diffractometer Program' _computing_data_collection 'P3/P4-PC Diffractometer Program (Siemens, 1991)' _computing_data_reduction 'XDISK in SHELXTL/PC (Sheldrick, 1990)' _computing_molecular_graphics 'XP in SHELXTL/PC' _computing_publication_material 'XPUBL in SHELXTL/PC' _computing_structure_refinement 'XLS in SHELXTL/PC' _computing_structure_solution 'XS in SHELXTL/PC' _diffrn_ambient_temperature 295 _diffrn_measurement_device 'Siemens R3m/V difractometer' _diffrn_measurement_method 2\q/\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.01 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2352 _diffrn_reflns_reduction_process 2208 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 1.5 _diffrn_standards_decay_% none _diffrn_standards_interval_count 'every 48 reflections' _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type N/A _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.176 _exptl_crystal_description prism _exptl_crystal_F_000 356 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.19 _refine_diff_density_min -0.14 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.24 _refine_ls_hydrogen_treatment 'ref with fixed U=U(eq) of bonded atom' _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 309 _refine_ls_number_reflns 1745 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_shift/esd_max 0.010 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(F) + 0.0005F^2^]' _refine_ls_wR_factor_all 0.0441 _refine_ls_wR_factor_obs .0423 _reflns_number_observed 1745 _reflns_number_total 2352 _reflns_observed_criterion refl_observed_if_F>_4.0_sigma(F) _[local]_cod_data_source_file sx1001.cif _[local]_cod_data_source_block default _[local]_cod_cif_authors_sg_H-M 'P 21' _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: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 23 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2006162 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z 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 _atom_site_aniso_type_symbol O1 .0520(10) .058(2) .0600(10) -.0070(10) .0110(10) .0170(10) O O2 .0410(10) .0460(10) .0440(10) .0000(10) .0100(10) -.0070(10) O O3 .0390(10) .0330(10) .0410(10) .0020(10) .0000(10) .0010(10) O C1 .049(2) .0320(10) .047(2) -.0040(10) .0060(10) .0080(10) C C2 .058(2) .043(2) .053(2) .001(2) -.0010(10) .020(2) C C3 .055(2) .057(2) .044(2) .000(2) -.0040(10) .012(2) C C4 .043(2) .0430(10) .0440(10) -.0020(10) -.0040(10) .0030(10) C C5 .0320(10) .0300(10) .0370(10) -.0020(10) .0070(10) -.0010(10) C C6 .0390(10) .0290(10) .0470(10) -.0050(10) .0000(10) .0010(10) C C7 .046(2) .0250(10) .0460(10) -.0010(10) .0050(10) .0040(10) C C8 .0360(10) .0280(10) .0350(10) .0000(10) .0040(10) .0030(10) C C9 .0360(10) .0250(10) .0340(10) -.0040(10) .0060(10) -.0020(10) C C10 .0370(10) .0260(10) .0360(10) .0010(10) .0050(10) .0040(10) C C11 .058(2) .0290(10) .043(2) -.0080(10) .0000(10) -.0010(10) C C12 .049(2) .041(2) .051(2) -.0150(10) -.0050(10) -.0010(10) C C13 .0430(10) .0450(10) .0420(10) -.0020(10) -.0030(10) -.0010(10) C C14 .047(2) .064(2) .054(2) .000(2) -.0060(10) .002(2) C C15 .047(2) .069(2) .072(2) .011(2) .003(2) .012(2) C C16 .070(2) .052(2) .046(2) .002(2) -.005(2) -.0010(10) C C17 .048(2) .047(2) .0410(10) .0040(10) .0100(10) .0080(10) C C18 .063(2) .058(2) .053(2) -.007(2) -.009(2) -.008(2) C C19 .042(2) .060(2) .066(2) .002(2) -.0090(10) .003(2) C C20 .050(2) .0390(10) .045(2) .0120(10) .0070(10) -.0010(10) C loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol O1 .4744(3) .0205(3) .9846(3) .0570(10) Uani ? ? O O2 .5805(2) .2573(3) .9856(2) .0430(10) Uani ? ? O O3 .4081(2) .2869(3) .5773(2) .0380(10) Uani ? ? O C1 .6256(3) 0 .9273(3) .0430(10) Uani ? ? C C2 .7499(4) -.0227(4) 1.0427(3) .0520(10) Uani ? ? C C3 .7940(4) .0893(4) 1.1238(3) .0520(10) Uani ? ? C C4 .8490(3) .1941(4) 1.0355(3) .0430(10) Uani ? ? C C5 .7202(3) .2168(3) .9166(3) .0330(10) Uani ? ? C C6 .7616(3) .3188(3) .8186(3) .0390(10) Uani ? ? C C7 .6236(3) .3507(3) .7178(3) .0390(10) Uani ? ? C C8 .5599(3) .2441(3) .6335(2) .0330(10) Uani ? ? C C9 .5288(3) .1392(3) .7315(3) .0320(10) Uani ? ? C C10 .6722(3) .1026(3) .8290(3) .0330(10) Uani ? ? C C11 .4436(3) .0388(3) .6504(3) .0440(10) Uani ? ? C C12 .2852(3) .0885(4) .5979(3) .0470(10) Uani ? ? C C13 .2978(3) .2049(4) .5134(3) .0430(10) Uani ? ? C C14 .1406(4) .2677(4) .5118(3) .0550(10) Uani ? ? C C15 .1110(4) .3716(4) .5657(4) .0620(10) Uani ? ? C C16 .3367(5) .1795(4) .3616(3) .0560(10) Uani ? ? C C17 .6708(4) .2201(4) .5139(3) .0450(10) Uani ? ? C C18 .8633(5) .3041(4) 1.1309(4) .0580(10) Uani ? ? C C19 1.0151(4) .1692(5) .9835(4) .0560(10) Uani ? ? C C20 .8063(4) .0502(4) .7434(3) .0440(10) Uani ? ? C H1O1 .457(5) .077(4) 1.008(4) .057 Uiso calc O1 H H1O2 .542(4) .219(4) .999(4) .043 Uiso calc O2 H H1A .618(3) -.072(3) .870(3) .043 Uiso calc C1 H H2A .711(4) -.076(3) 1.110(3) .052 Uiso calc C2 H H2B .844(4) -.058(3) 1.003(3) .052 Uiso calc C2 H H3A .702(4) .111(3) 1.176(3) .052 Uiso calc C3 H H3B .876(4) .070(3) 1.193(3) .052 Uiso calc C3 H H6A .791(3) .389(3) .866(3) .039 Uiso calc C6 H H6B .851(3) .300(3) .769(3) .039 Uiso calc C6 H H7A .650(3) .418(3) .658(3) .039 Uiso calc C7 H H7B .537(4) .385(3) .766(3) .039 Uiso calc C7 H H9A .454(3) .170(3) .792(3) .032 Uiso calc C9 H H11A .419(3) -.029(3) .711(3) .044 Uiso calc C11 H H11B .506(3) .009(3) .575(3) .044 Uiso calc C11 H H12A .215(3) .107(3) .682(3) .047 Uiso calc C12 H H12B .226(4) .036(3) .545(3) .047 Uiso calc C12 H H14A .063(4) .225(3) .470(3) .055 Uiso calc C14 H H15A .191(4) .417(3) .603(4) .062 Uiso calc C15 H H15B .004(4) .404(3) .557(3) .062 Uiso calc C15 H H16A .246(4) .146(3) .319(3) .056 Uiso calc C16 H H16B .427(4) .133(3) .360(3) .056 Uiso calc C16 H H16C .365(4) .251(3) .317(3) .056 Uiso calc C16 H H17A .777(4) .231(3) .542(3) .045 Uiso calc C17 H H17B .662(3) .138(3) .470(3) .045 Uiso calc C17 H H17C .650(3) .273(3) .447(3) .045 Uiso calc C17 H H18A .892(4) .370(4) 1.081(4) .058 Uiso calc C18 H H18B .954(4) .283(3) 1.205(3) .058 Uiso calc C18 H H18C .768(4) .323(3) 1.170(3) .058 Uiso calc C18 H H19A 1.031(4) .094(4) .941(3) .056 Uiso calc C19 H H19B 1.049(4) .232(3) .920(3) .056 Uiso calc C19 H H19C 1.081(4) .171(3) 1.055(4) .056 Uiso calc C19 H H20A .880(3) -.006(3) .796(3) .044 Uiso calc C20 H H20B .764(3) .012(3) .669(3) .044 Uiso calc C20 H H20C .868(3) .118(3) .701(3) .044 Uiso calc C20 H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.432(4) yes O2 C5 . . 1.452(3) yes O3 C8 . . 1.456(3) yes O3 C13 . . 1.431(4) yes C1 C2 . . 1.524(4) yes C1 C10 . . 1.548(4) yes C2 C3 . . 1.514(6) yes C3 C4 . . 1.530(5) yes C4 C5 . . 1.573(4) yes C4 C18 . . 1.537(6) yes C4 C19 . . 1.537(5) yes C5 C6 . . 1.529(5) yes C5 C10 . . 1.573(5) yes C6 C7 . . 1.533(4) yes C7 C8 . . 1.527(5) yes C8 C9 . . 1.534(4) yes C8 C17 . . 1.539(4) yes C9 C10 . . 1.561(4) yes C9 C11 . . 1.531(5) yes C10 C20 . . 1.545(4) yes C11 C12 . . 1.520(4) yes C12 C13 . . 1.539(5) yes C13 C14 . . 1.504(5) yes C13 C16 . . 1.540(4) yes C14 C15 . . 1.298(6) yes loop_ _refine_ls_R_factor_obs .0380 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 0 0 4 2 -2 4 -2 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 C8 O3 C13 120.2(3) yes O1 C1 C2 110.3(2) yes O1 C1 C10 111.8(2) yes C2 C1 C10 112.7(2) yes C1 C2 C3 112.9(3) yes C2 C3 C4 114.7(3) yes C3 C4 C5 108.2(3) yes C3 C4 C18 107.2(3) yes C5 C4 C18 110.2(3) yes C3 C4 C19 110.3(3) yes C5 C4 C19 114.0(2) yes C18 C4 C19 106.8(3) yes O2 C5 C4 105.6(2) yes O2 C5 C6 105.2(3) yes C4 C5 C6 113.7(2) yes O2 C5 C10 107.5(2) yes C4 C5 C10 114.8(3) yes C6 C5 C10 109.3(2) yes C5 C6 C7 112.2(2) yes C6 C7 C8 113.7(3) yes O3 C8 C7 103.4(3) yes O3 C8 C9 108.1(2) yes C7 C8 C9 109.3(2) yes O3 C8 C17 109.5(2) yes C7 C8 C17 108.7(2) yes C9 C8 C17 117.0(3) yes C8 C9 C10 115.0(2) yes C8 C9 C11 109.3(2) yes C10 C9 C11 117.2(3) yes C1 C10 C5 109.6(2) yes C1 C10 C9 110.6(2) yes C5 C10 C9 106.9(3) yes C1 C10 C20 105.0(3) yes C5 C10 C20 114.4(2) yes C9 C10 C20 110.3(2) yes C9 C11 C12 107.2(3) yes C11 C12 C13 114.0(3) yes O3 C13 C12 111.6(2) yes O3 C13 C14 105.6(3) yes C12 C13 C14 108.6(3) yes O3 C13 C16 111.5(3) yes C12 C13 C16 111.8(3) yes C14 C13 C16 107.3(3) yes C13 C14 C15 126.6(3) yes