#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/62/2006225.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_2006225 loop_ _publ_author_name 'Damas, Ana M.' 'Kijjoa, Anake' 'Pinto, Madalena' _publ_section_title ; Two Dolabrane-type Diterpenoids ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 755 _journal_page_last 757 _journal_paper_doi 10.1107/S0108270196015752 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C19 H31 Cl O4' _chemical_formula_sum 'C19 H31 Cl O4' _chemical_formula_weight 358.89 _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' _audit_creation_method SHELXL _cell_angle_alpha 90 _cell_angle_beta 96.56(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.2570(10) _cell_length_b 15.137(3) _cell_length_c 9.819(2) _cell_measurement_reflns_used 1404 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.1 _cell_measurement_theta_min 4.8 _cell_volume 923.9(3) _computing_cell_refinement 'Stoe IPDS software package' _computing_data_collection 'Stoe IPDS software package' _computing_data_reduction 'Stoe IPDS software package' _computing_molecular_graphics ; ORTEP (Zsolnai & Pritzkow, 1995) and XPMA (Zsolnai, 1996) ; _computing_publication_material 'SHELXL93 and ORTEP' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Stoe IPDS' _diffrn_measurement_method 'image plate' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoKa _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10929 _diffrn_reflns_theta_max 28.13 _diffrn_reflns_theta_min 5.39 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 4 _diffrn_standards_number 100 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.140 _refine_diff_density_min -0.196 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.04(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.057 _refine_ls_goodness_of_fit_obs 1.048 _refine_ls_hydrogen_treatment 'H atoms refined isotropically' _refine_ls_matrix_type full _refine_ls_number_parameters 341 _refine_ls_number_reflns 4083 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.048 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_obs .0316 _refine_ls_shift/esd_max -0.117 _refine_ls_shift/esd_mean 0.008 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.1319P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0801 _refine_ls_wR_factor_obs .0775 _reflns_number_observed 3934 _reflns_number_total '4086 (91% of theoretical)' _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1184.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.1319P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.1319P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2006225 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -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 Cl1 .0770(3) .0389(2) .0673(3) -.0066(2) .0161(2) .0139(2) O1 .0570(8) .0500(7) .0579(7) -.0029(6) .0136(6) -.0162(6) O2 .0470(7) .0613(7) .0480(6) -.0147(6) .0073(5) -.0149(6) O3 .0421(7) .0637(7) .0616(7) .0116(6) -.0098(5) -.0089(7) O4 .0447(6) .0428(6) .0308(5) .0014(5) .0075(4) .0036(4) C1 .0401(9) .0330(7) .0428(7) .0031(6) -.0021(6) .0001(6) C2 .0456(9) .0299(6) .0389(7) -.0012(5) .0033(6) .0036(6) C4 .0396(8) .0466(8) .0320(6) -.0015(6) .0014(5) .0044(5) C5 .0361(8) .0388(7) .0323(6) .0010(5) .0044(5) .0060(5) C6 .0456(9) .0490(8) .0329(6) .0081(7) .0120(5) .0032(6) C7 .0585(11) .0379(7) .0307(6) .0081(7) .0089(6) -.0024(5) C8 .0362(8) .0324(6) .0308(6) .0033(5) .0058(5) .0005(5) C9 .0316(7) .0310(6) .0300(6) -.0002(5) .0041(5) -.0007(4) C10 .0300(7) .0331(6) .0349(6) -.0006(5) .0009(5) .0024(5) C11 .0448(8) .0308(6) .0307(6) .0029(5) .0042(5) -.0016(5) C12 .0444(9) .0357(7) .0282(6) .0029(6) .0062(5) .0006(5) C13 .0346(7) .0320(6) .0309(6) .0005(5) .0038(5) .0025(5) C14 .0462(9) .0311(6) .0314(6) .0016(6) .0050(5) .0001(5) C15 .0367(8) .0348(7) .0313(6) -.0017(5) .0032(5) .0015(5) C16 .0524(10) .0340(7) .0413(7) -.0008(6) .0104(7) .0025(6) C17 .0376(8) .0437(8) .0450(8) -.0033(6) .0026(6) .0073(6) C18 .0552(12) .0684(12) .0447(9) -.0041(9) -.0045(8) -.0093(8) C19 .0459(10) .0545(11) .0494(8) -.0021(7) .0101(7) .0175(7) C20 .0343(8) .0429(7) .0392(7) -.0021(6) .0057(5) .0014(6) 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Cl1 .28105(9) .21824(3) .96692(5) .06047(14) Uani d . 1 . Cl O1 .3509(2) -.42931(9) 1.19301(13) .0544(3) Uani d . 1 . O O2 .0655(2) -.39485(9) 1.29708(13) .0519(3) Uani d . 1 . O O3 .6915(2) -.27905(11) 1.62122(13) .0570(3) Uani d . 1 . O O4 .2355(2) .02294(7) .88894(10) .0392(2) Uani d . 1 . O C1 .3999(3) -.33548(9) 1.3910(2) .0392(3) Uani d . 1 . C C2 .2729(3) -.39013(9) 1.28249(15) .0383(3) Uani d . 1 . C C4 .5711(3) -.21994(11) 1.64498(14) .0396(3) Uani d . 1 . C C5 .3328(2) -.22394(10) 1.58552(14) .0357(3) Uani d . 1 . C C6 .2047(3) -.13912(12) 1.6081(2) .0419(3) Uani d . 1 . C C7 .2484(3) -.06157(10) 1.51655(14) .0421(3) Uani d . 1 . C C8 .2097(3) -.08845(9) 1.36606(14) .0330(3) Uani d . 1 . C C9 .3484(2) -.16918(9) 1.33438(13) .0308(3) Uani d . 1 . C C10 .2963(2) -.24720(9) 1.42947(14) .0329(3) Uani d . 1 . C C11 .2751(3) -.19358(9) 1.18390(13) .0354(3) Uani d . 1 . C C12 .2963(3) -.11746(9) 1.08282(14) .0359(3) Uani d . 1 . C C13 .1801(2) -.03188(9) 1.11700(13) .0325(3) Uani d . 1 . C C14 .2363(3) -.01001(9) 1.27076(14) .0362(3) Uani d . 1 . C C15 .2646(3) .04419(9) 1.03214(14) .0343(3) Uani d . 1 . C C16 .1551(3) .13195(10) 1.0539(2) .0422(3) Uani d . 1 . C C17 -.0624(3) -.04238(11) 1.0813(2) .0422(3) Uani d . 1 . C C18 .6514(4) -.1472(2) 1.7415(2) .0569(5) Uani d . 1 . C C19 .2408(3) -.29784(13) 1.6717(2) .0496(4) Uani d . 1 . C C20 .5885(2) -.14665(11) 1.3517(2) .0387(3) Uani d . 1 . C H1A .425(4) -.3732(16) 1.473(2) .062(6) Uiso d . 1 . H H1B .540(4) -.3269(13) 1.3625(19) .043(5) Uiso d . 1 . H H2 .003(4) -.4281(17) 1.235(3) .069(7) Uiso d . 1 . H H4 .336(5) .0458(19) .854(3) .072(8) Uiso d . 1 . H H6A .043(4) -.1565(13) 1.587(2) .049(5) Uiso d . 1 . H H6B .224(4) -.1213(14) 1.707(2) .056(6) Uiso d . 1 . H H7A .143(4) -.0110(15) 1.533(2) .055(5) Uiso d . 1 . H H7B .393(4) -.0384(14) 1.5383(19) .044(5) Uiso d . 1 . H H8 .065(3) -.1091(12) 1.3510(18) .038(4) Uiso d . 1 . H H10 .140(4) -.2556(13) 1.410(2) .048(5) Uiso d . 1 . H H11A .361(3) -.2401(13) 1.1569(19) .038(4) Uiso d . 1 . H H11B .112(3) -.2121(12) 1.1775(17) .036(4) Uiso d . 1 . H H12A .453(3) -.1057(12) 1.0749(17) .035(4) Uiso d . 1 . H H12B .244(4) -.1411(16) .994(2) .057(6) Uiso d . 1 . H H14A .384(4) .0117(15) 1.285(2) .050(5) Uiso d . 1 . H H14B .140(3) .0406(14) 1.295(2) .048(5) Uiso d . 1 . H H15 .418(3) .0504(12) 1.0595(17) .034(4) Uiso d . 1 . H H16A -.004(4) .1323(13) 1.009(2) .045(5) Uiso d . 1 . H H16B .179(5) .1472(16) 1.156(3) .068(7) Uiso d . 1 . H H17A -.119(3) -.0987(13) 1.1262(18) .037(4) Uiso d . 1 . H H17B -.090(4) -.0448(17) .985(3) .068(7) Uiso d . 1 . H H17C -.138(5) .0058(18) 1.121(3) .072(7) Uiso d . 1 . H H18A .632(5) -.084(2) 1.705(3) .083(8) Uiso d . 1 . H H18B .549(5) -.145(2) 1.810(3) .084(8) Uiso d . 1 . H H18C .811(5) -.160(2) 1.773(3) .086(8) Uiso d . 1 . H H19A .099(5) -.3064(16) 1.641(3) .063(7) Uiso d . 1 . H H19B .318(5) -.354(2) 1.673(3) .081(8) Uiso d . 1 . H H19C .238(4) -.2796(19) 1.769(2) .066(6) Uiso d . 1 . H H20A .620(4) -.0974(17) 1.286(2) .066(6) Uiso d . 1 . H H20B .639(4) -.1239(16) 1.436(3) .064(6) Uiso d . 1 . H H20C .679(4) -.1987(18) 1.335(2) .070(7) Uiso d . 1 . H 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' Cl Cl 0.1484 0.1585 '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 C2 O2 H2 109.3(18) ? C15 O4 H4 107.0(19) ? C2 C1 C10 116.43(13) no C2 C1 H1A 106.5(14) ? C10 C1 H1A 109.3(14) ? C2 C1 H1B 107.1(12) ? C10 C1 H1B 112.1(12) ? H1A C1 H1B 104.6(18) ? O1 C2 O2 122.30(15) no O1 C2 C1 124.2(2) no O2 C2 C1 113.48(14) no O3 C4 C18 119.6(2) no O3 C4 C5 119.69(14) no C18 C4 C5 120.54(15) no C4 C5 C6 114.17(13) no C4 C5 C19 103.02(12) no C6 C5 C19 106.87(13) no C4 C5 C10 114.06(12) no C6 C5 C10 107.93(11) no C19 C5 C10 110.49(13) no C7 C6 C5 115.21(12) no C7 C6 H6A 108.2(11) ? C5 C6 H6A 105.6(11) ? C7 C6 H6B 110.9(12) ? C5 C6 H6B 110.8(13) ? H6A C6 H6B 105.4(17) ? C6 C7 C8 110.30(13) no C6 C7 H7A 108.7(12) ? C8 C7 H7A 108.2(12) ? C6 C7 H7B 111.9(12) ? C8 C7 H7B 110.5(11) ? H7A C7 H7B 106.9(18) ? C7 C8 C14 111.63(12) no C7 C8 C9 111.97(11) no C14 C8 C9 112.70(11) no C7 C8 H8 106.2(10) ? C14 C8 H8 109.1(11) ? C9 C8 H8 104.7(11) ? C20 C9 C11 109.88(12) no C20 C9 C8 111.51(12) no C11 C9 C8 105.63(11) no C20 C9 C10 111.78(12) no C11 C9 C10 109.40(11) no C8 C9 C10 108.43(11) no C1 C10 C9 112.60(12) no C1 C10 C5 114.47(11) no C9 C10 C5 113.46(11) no C1 C10 H10 105.9(11) ? C9 C10 H10 104.5(12) ? C5 C10 H10 104.8(11) ? C12 C11 C9 113.67(11) no C12 C11 H11A 106.6(11) ? C9 C11 H11A 109.5(11) ? C12 C11 H11B 108.4(10) ? C9 C11 H11B 107.5(9) ? H11A C11 H11B 111.3(15) ? C11 C12 C13 114.34(11) no C11 C12 H12A 109.8(10) ? C13 C12 H12A 110.9(10) ? C11 C12 H12B 105.0(14) ? C13 C12 H12B 112.8(14) ? H12A C12 H12B 103.3(17) ? C17 C13 C12 110.11(12) no C17 C13 C14 110.83(12) no C12 C13 C14 109.41(11) no C17 C13 C15 110.18(12) no C12 C13 C15 108.02(11) no C14 C13 C15 108.21(11) no C8 C14 C13 113.69(11) no C8 C14 H14A 109.8(12) ? C13 C14 H14A 108.7(12) ? C8 C14 H14B 109.5(12) ? C13 C14 H14B 108.1(11) ? H14A C14 H14B 106.9(17) ? O4 C15 C16 108.95(12) no O4 C15 C13 110.36(11) no C16 C15 C13 112.78(12) no O4 C15 H15 107.7(10) ? C16 C15 H15 108.9(11) ? C13 C15 H15 108.0(11) ? C15 C16 Cl1 109.91(11) no C15 C16 H16A 111.7(11) ? Cl1 C16 H16A 104.3(11) ? C15 C16 H16B 108.4(15) ? Cl1 C16 H16B 106.2(14) ? H16A C16 H16B 115.9(19) ? C13 C17 H17A 111.3(10) ? C13 C17 H17B 107.5(15) ? H17A C17 H17B 111.1(19) ? C13 C17 H17C 110.2(16) ? H17A C17 H17C 103.9(18) ? H17B C17 H17C 113.(2) ? C4 C18 H18A 116.6(16) ? C4 C18 H18B 105.2(18) ? H18A C18 H18B 98.(2) ? C4 C18 H18C 107.3(16) ? H18A C18 H18C 110.(2) ? H18B C18 H18C 120.(2) ? C5 C19 H19A 109.1(15) ? C5 C19 H19B 114.9(17) ? H19A C19 H19B 110.(2) ? C5 C19 H19C 111.7(16) ? H19A C19 H19C 104.(2) ? H19B C19 H19C 107.(2) ? C9 C20 H20A 110.3(14) ? C9 C20 H20B 114.6(15) ? H20A C20 H20B 103.(2) ? C9 C20 H20C 111.8(15) ? H20A C20 H20C 109.(2) ? H20B C20 H20C 108.(2) ? 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 Cl1 C16 . 1.791(2) yes O1 C2 . 1.208(2) yes O2 C2 . 1.324(2) yes O2 H2 . .85(3) ? O3 C4 . 1.209(2) yes O4 C15 . 1.434(2) yes O4 H4 . .82(3) ? C1 C2 . 1.503(2) yes C1 C10 . 1.551(2) yes C1 H1A . .99(2) ? C1 H1B . .96(2) ? C4 C18 . 1.502(2) yes C4 C5 . 1.539(2) yes C5 C6 . 1.543(2) yes C5 C19 . 1.553(2) yes C5 C10 . 1.563(2) yes C6 C7 . 1.522(2) yes C6 H6A . 1.04(2) ? C6 H6B . 1.00(2) ? C7 C8 . 1.525(2) yes C7 H7A . 1.03(2) ? C7 H7B . .97(2) ? C8 C14 . 1.533(2) yes C8 C9 . 1.551(2) yes C8 H8 . .95(2) ? C9 C20 . 1.531(2) yes C9 C11 . 1.541(2) yes C9 C10 . 1.563(2) yes C10 H10 . .98(2) ? C11 C12 . 1.536(2) yes C11 H11A . .94(2) ? C11 H11B . 1.05(2) ? C12 C13 . 1.541(2) yes C12 H12A . 1.01(2) ? C12 H12B . .96(2) ? C13 C17 . 1.526(2) yes C13 C14 . 1.546(2) yes C13 C15 . 1.549(2) yes C14 H14A . .98(2) ? C14 H14B . 1.02(2) ? C15 C16 . 1.521(2) yes C15 H15 . .97(2) ? C16 H16A . 1.04(2) ? C16 H16B . 1.02(3) ? C17 H17A . 1.04(2) ? C17 H17B . .94(2) ? C17 H17C . .98(3) ? C18 H18A . 1.02(3) ? C18 H18B . .98(3) ? C18 H18C . 1.03(3) ? C19 H19A . .92(3) ? C19 H19B . .97(3) ? C19 H19C . 1.00(2) ? C20 H20A . 1.02(3) ? C20 H20B . .92(2) ? C20 H20C . .99(3) ? 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 139.7(2) ? C10 C1 C2 O2 -43.1(2) ? O3 C4 C5 C6 -172.52(14) ? C18 C4 C5 C6 12.5(2) ? O3 C4 C5 C19 72.0(2) ? C18 C4 C5 C19 -102.9(2) ? O3 C4 C5 C10 -47.8(2) ? C18 C4 C5 C10 137.3(2) ? C4 C5 C6 C7 75.1(2) ? C19 C5 C6 C7 -171.68(15) ? C5 C6 C7 C8 55.4(2) no C6 C7 C8 C9 -56.7(2) no C7 C8 C9 C10 57.3(2) no C8 C9 C10 C5 -56.73(15) no C9 C10 C5 C6 53.6(2) no C10 C5 C6 C7 -52.8(2) no C6 C7 C8 C14 175.85(13) ? C7 C8 C9 C20 -66.1(2) ? C14 C8 C9 C20 60.70(15) ? C7 C8 C9 C11 174.53(13) ? C8 C9 C11 C12 57.2(2) no C9 C11 C12 C13 -54.9(2) no C11 C12 C13 C14 47.5(2) no C12 C13 C14 C8 -49.1(2) no C13 C14 C8 C9 57.8(2) no C14 C8 C9 C11 -58.63(15) no C14 C8 C9 C10 -175.81(12) ? C2 C1 C10 C9 -86.6(2) ? C2 C1 C10 C5 141.87(14) ? C20 C9 C10 C1 -65.5(2) ? C11 C9 C10 C1 56.5(2) ? C8 C9 C10 C1 171.22(11) ? C20 C9 C10 C5 66.6(2) ? C11 C9 C10 C5 -171.46(11) ? C4 C5 C10 C1 56.7(2) ? C6 C5 C10 C1 -175.31(13) ? C19 C5 C10 C1 -58.8(2) ? C4 C5 C10 C9 -74.5(2) ? C19 C5 C10 C9 170.06(13) ? C20 C9 C11 C12 -63.2(2) ? C10 C9 C11 C12 173.70(12) ? C11 C12 C13 C17 -74.5(2) ? C11 C12 C13 C15 165.11(12) ? C7 C8 C14 C13 -175.13(13) ? C17 C13 C14 C8 72.5(2) ? C15 C13 C14 C8 -166.61(13) ? C17 C13 C15 O4 -64.4(2) ? C12 C13 C15 O4 55.9(2) ? C14 C13 C15 O4 174.28(12) ? C17 C13 C15 C16 57.7(2) ? C12 C13 C15 C16 178.03(12) ? C14 C13 C15 C16 -63.6(2) ? O4 C15 C16 Cl1 -63.20(15) ? C13 C15 C16 Cl1 173.89(10) ?