#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015253.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_2015253 loop_ _publ_author_name 'Zhang, Yi-Xun' 'Jackson, Shauntina H.' 'Rajab, Mohamed S.' 'Fronczek, Frank R.' 'Watkins, Steven F.' _publ_section_title ; Cinnamolid-3\b-ol hemihydrate and 3\b-hydroxycinnamolide acetate, two drimanolide-class sesquiterpene lactones from Warburgia ugandensis ; _journal_coeditor_code GZ3003 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o219 _journal_page_last o221 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C17 H24 O4' _chemical_formula_moiety 'C17 H24 O4' _chemical_formula_sum 'C17 H24 O4' _chemical_formula_weight 292.36 _chemical_name_common ; cinnamolide-3\b-ol-acetate ; _chemical_name_systematic ; 3\b-Acetoxy-7-drimen-12,11-olide ; _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 SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 101.22(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.802(3) _cell_length_b 7.918(4) _cell_length_c 14.302(8) _cell_measurement_reflns_used 2218 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.0 _cell_measurement_theta_min 2.5 _cell_volume 755.6(7) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor 1997)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction 'HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 120 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'Nonius KappaCCD area-detector (with Oxford Cryostream)' _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 0.057 _diffrn_reflns_av_sigmaI/netI 0.0883 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 8695 _diffrn_reflns_theta_full 30.0 _diffrn_reflns_theta_max 30.0 _diffrn_reflns_theta_min 2.9 _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.22 _refine_diff_density_min -0.20 _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2353 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.982 _refine_ls_R_factor_all 0.109 _refine_ls_R_factor_gt 0.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0473P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.090 _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1456 _reflns_number_total 2353 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gz3003.cif _[local]_cod_data_source_block II _[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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2015253 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _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 O O1 0.8176(3) 0.4883(3) 0.55905(12) 0.0373(5) Uani d . 1 O O2 0.9004(3) 0.7238(3) 0.64502(13) 0.0466(6) Uani d . 1 O O3 0.2946(2) 0.7821(3) 0.03214(12) 0.0303(5) Uani d . 1 O O4 -0.0282(3) 0.7133(3) 0.02549(13) 0.0421(6) Uani d . 1 C C1 0.5137(4) 0.5137(4) 0.24430(18) 0.0291(6) Uani d . 1 H H1A 0.5911 0.4071 0.2488 0.035 Uiso calc R 1 H H1B 0.3883 0.4910 0.2675 0.035 Uiso calc R 1 C C2 0.4608(4) 0.5684(4) 0.13965(18) 0.0281(6) Uani d . 1 H H2A 0.5848 0.5818 0.1138 0.034 Uiso calc R 1 H H2B 0.3767 0.4811 0.1017 0.034 Uiso calc R 1 C C3 0.3484(4) 0.7340(4) 0.13273(17) 0.0272(6) Uani d . 1 H H3 0.2227 0.7178 0.1581 0.033 Uiso calc R 1 C C4 0.4685(4) 0.8808(4) 0.18701(18) 0.0277(6) Uani d . 1 C C5 0.5321(4) 0.8218(4) 0.29222(18) 0.0273(6) Uani d . 1 H H5 0.4030 0.8075 0.3150 0.033 Uiso calc R 1 C C6 0.6462(4) 0.9594(4) 0.35766(18) 0.0314(7) Uani d . 1 H H6A 0.7580 1.0015 0.3290 0.038 Uiso calc R 1 H H6B 0.5544 1.0553 0.3609 0.038 Uiso calc R 1 C C7 0.7284(4) 0.8995(4) 0.45640(19) 0.0307(7) Uani d . 1 H H7 0.7873 0.9790 0.5033 0.037 Uiso calc R 1 C C8 0.7213(4) 0.7382(4) 0.48037(18) 0.0298(7) Uani d . 1 C C9 0.6281(4) 0.6011(4) 0.41395(19) 0.0307(7) Uani d . 1 H H9 0.4839 0.5919 0.4190 0.037 Uiso calc R 1 C C10 0.6365(4) 0.6465(4) 0.30899(18) 0.0265(6) Uani d . 1 C C11 0.7360(4) 0.4441(4) 0.45954(19) 0.0327(7) Uani d . 1 H H11A 0.6413 0.3483 0.4562 0.039 Uiso calc R 1 H H11B 0.8452 0.4117 0.4263 0.039 Uiso calc R 1 C C12 0.8213(4) 0.6600(4) 0.5705(2) 0.0337(7) Uani d . 1 C C13 0.3243(4) 1.0323(4) 0.1838(2) 0.0392(8) Uani d . 1 H H13A 0.2183 1.0040 0.2187 0.059 Uiso calc R 1 H H13B 0.2643 1.0581 0.1173 0.059 Uiso calc R 1 H H13C 0.3988 1.1309 0.2132 0.059 Uiso calc R 1 C C14 0.6407(4) 0.9339(4) 0.1383(2) 0.0362(7) Uani d . 1 H H14A 0.7388 0.9999 0.1830 0.054 Uiso calc R 1 H H14B 0.5877 1.0027 0.0821 0.054 Uiso calc R 1 H H14C 0.7057 0.8330 0.1187 0.054 Uiso calc R 1 C C15 0.8545(3) 0.6492(4) 0.29435(18) 0.0310(7) Uani d . 1 H H15A 0.9130 0.5362 0.3063 0.047 Uiso calc R 1 H H15B 0.9322 0.7300 0.3387 0.047 Uiso calc R 1 H H15C 0.8573 0.6829 0.2287 0.047 Uiso calc R 1 C C16 0.1016(4) 0.7681(4) -0.01206(18) 0.0278(6) Uani d . 1 C C17 0.0738(4) 0.8303(4) -0.11191(18) 0.0316(7) Uani d . 1 H H17A -0.0402 0.7720 -0.1512 0.047 Uiso calc R 1 H H17B 0.1953 0.8077 -0.1371 0.047 Uiso calc R 1 H H17C 0.0480 0.9521 -0.1132 0.047 Uiso calc R 1 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 0.0408(11) 0.0408(15) 0.0292(11) 0.0011(10) 0.0044(8) 0.0066(10) O2 0.0573(12) 0.0554(15) 0.0253(10) -0.0093(13) 0.0034(9) 0.0001(11) O3 0.0265(9) 0.0368(13) 0.0257(9) -0.0003(9) 0.0004(7) -0.0002(8) O4 0.0322(10) 0.0568(15) 0.0349(12) -0.0113(11) 0.0003(8) 0.0074(11) C1 0.0292(13) 0.0250(16) 0.0326(15) -0.0013(12) 0.0048(12) -0.0010(13) C2 0.0299(13) 0.0237(17) 0.0280(14) -0.0027(13) -0.0007(11) -0.0022(13) C3 0.0267(12) 0.0302(17) 0.0241(14) -0.0004(13) 0.0033(10) -0.0004(13) C4 0.0268(12) 0.0263(16) 0.0285(15) 0.0013(12) 0.0016(11) -0.0007(13) C5 0.0261(12) 0.0241(16) 0.0304(15) 0.0042(12) 0.0024(11) -0.0016(13) C6 0.0319(13) 0.0263(17) 0.0344(15) 0.0033(13) 0.0024(12) -0.0024(13) C7 0.0280(14) 0.0361(19) 0.0267(14) 0.0001(13) 0.0018(11) -0.0081(14) C8 0.0258(13) 0.0349(19) 0.0282(15) 0.0021(13) 0.0045(11) -0.0008(14) C9 0.0291(12) 0.0287(17) 0.0335(15) 0.0016(13) 0.0045(11) 0.0007(13) C10 0.0282(12) 0.0260(16) 0.0239(13) 0.0017(12) 0.0015(10) 0.0026(12) C11 0.0309(14) 0.0364(19) 0.0293(15) 0.0038(14) 0.0021(12) 0.0019(13) C12 0.0314(14) 0.043(2) 0.0285(15) -0.0039(14) 0.0095(12) -0.0001(14) C13 0.0440(15) 0.0298(18) 0.0390(17) 0.0096(14) -0.0038(13) -0.0043(14) C14 0.0384(14) 0.0350(19) 0.0325(14) -0.0072(13) 0.0000(12) 0.0020(13) C15 0.0294(12) 0.0306(17) 0.0325(14) 0.0012(13) 0.0045(11) -0.0027(14) C16 0.0271(13) 0.0242(16) 0.0299(14) 0.0004(12) 0.0003(11) -0.0063(12) C17 0.0316(13) 0.0296(17) 0.0300(15) -0.0028(13) -0.0034(11) 0.0010(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 C12 O1 C11 110.4(2) C16 O3 C3 118.3(2) C2 C1 C10 113.0(2) C2 C1 H1A 109.0 C10 C1 H1A 109.0 C2 C1 H1B 109.0 C10 C1 H1B 109.0 H1A C1 H1B 107.8 C3 C2 C1 109.2(2) C3 C2 H2A 109.8 C1 C2 H2A 109.8 C3 C2 H2B 109.8 C1 C2 H2B 109.8 H2A C2 H2B 108.3 O3 C3 C2 108.4(2) O3 C3 C4 107.8(2) C2 C3 C4 114.20(19) O3 C3 H3 108.8 C2 C3 H3 108.8 C4 C3 H3 108.8 C14 C4 C3 110.8(2) C13 C4 C14 108.1(2) C3 C4 C13 107.4(2) C14 C4 C5 115.4(2) C3 C4 C5 106.3(2) C13 C4 C5 108.6(2) C6 C5 C4 112.8(2) C6 C5 C10 112.05(19) C4 C5 C10 116.8(2) C6 C5 H5 104.6 C4 C5 H5 104.6 C10 C5 H5 104.6 C7 C6 C5 113.6(3) C7 C6 H6A 108.8 C5 C6 H6A 108.8 C7 C6 H6B 108.8 C5 C6 H6B 108.8 H6A C6 H6B 107.7 C8 C7 C6 121.7(3) C8 C7 H7 119.1 C6 C7 H7 119.1 C7 C8 C12 126.7(3) C7 C8 C9 124.4(3) C12 C8 C9 108.5(3) C8 C9 C11 102.2(2) C8 C9 C10 110.7(2) C11 C9 C10 119.8(2) C8 C9 H9 107.9 C11 C9 H9 107.9 C10 C9 H9 107.9 C1 C10 C15 110.7(2) C1 C10 C9 107.8(2) C15 C10 C9 110.6(2) C1 C10 C5 109.84(19) C15 C10 C5 113.0(2) C9 C10 C5 104.7(2) O1 C11 C9 106.3(2) O1 C11 H11A 110.5 C9 C11 H11A 110.5 O1 C11 H11B 110.5 C9 C11 H11B 110.5 H11A C11 H11B 108.7 O2 C12 O1 121.1(3) O2 C12 C8 130.3(3) O1 C12 C8 108.6(2) C4 C13 H13A 109.5 C4 C13 H13B 109.5 H13A C13 H13B 109.5 C4 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C4 C14 H14A 109.5 C4 C14 H14B 109.5 H14A C14 H14B 109.5 C4 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C10 C15 H15A 109.5 C10 C15 H15B 109.5 H15A C15 H15B 109.5 C10 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 O4 C16 O3 123.7(2) O4 C16 C17 125.6(2) O3 C16 C17 110.7(2) C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C12 1.369(4) ? O1 C11 1.466(3) ? O2 C12 1.207(3) y O3 C16 1.346(3) ? O3 C3 1.464(3) ? O4 C16 1.201(3) y C1 C2 1.532(3) ? C1 C10 1.536(4) ? C1 H1A 0.9900 ? C1 H1B 0.9900 ? C2 C3 1.511(4) ? C2 H2A 0.9900 ? C2 H2B 0.9900 ? C3 C4 1.540(4) ? C3 H3 1.0000 ? C4 C13 1.544(4) ? C4 C14 1.534(4) ? C4 C5 1.555(4) ? C5 C6 1.544(4) ? C5 C10 1.556(4) ? C5 H5 1.0000 ? C6 C7 1.492(4) ? C6 H6A 0.9900 ? C6 H6B 0.9900 ? C7 C8 1.326(4) y C7 H7 0.9500 ? C8 C12 1.472(4) ? C8 C9 1.499(4) ? C9 C11 1.525(4) ? C9 C10 1.555(4) ? C9 H9 1.0000 ? C10 C15 1.537(3) ? C11 H11A 0.9900 ? C11 H11B 0.9900 ? C13 H13A 0.9800 ? C13 H13B 0.9800 ? C13 H13C 0.9800 ? C14 H14A 0.9800 ? C14 H14B 0.9800 ? C14 H14C 0.9800 ? C15 H15A 0.9800 ? C15 H15B 0.9800 ? C15 H15C 0.9800 ? C16 C17 1.488(4) ? C17 H17A 0.9800 ? C17 H17B 0.9800 ? C17 H17C 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 C3 -56.9(3) y C16 O3 C3 C2 107.0(2) ? C16 O3 C3 C4 -128.9(2) ? C1 C2 C3 O3 -178.54(19) ? C1 C2 C3 C4 61.2(3) y O3 C3 C4 C13 66.7(3) ? C2 C3 C4 C13 -172.7(2) ? O3 C3 C4 C14 -51.1(3) ? C2 C3 C4 C14 69.5(3) ? O3 C3 C4 C5 -177.18(19) ? C2 C3 C4 C5 -56.6(3) y C14 C4 C5 C6 59.5(3) ? C3 C4 C5 C6 -177.2(2) ? C13 C4 C5 C6 -61.9(3) ? C14 C4 C5 C10 -72.3(3) ? C3 C4 C5 C10 50.9(3) y C13 C4 C5 C10 166.2(2) ? C4 C5 C6 C7 -173.6(2) ? C10 C5 C6 C7 -39.4(3) y C5 C6 C7 C8 7.1(4) y C6 C7 C8 C12 170.7(2) ? C6 C7 C8 C9 -1.6(4) y C7 C8 C9 C11 156.4(3) ? C12 C8 C9 C11 -17.1(3) y C7 C8 C9 C10 27.8(4) y C12 C8 C9 C10 -145.7(2) ? C2 C1 C10 C15 -74.8(3) ? C2 C1 C10 C9 164.1(2) ? C2 C1 C10 C5 50.6(3) y C8 C9 C10 C1 -172.3(2) ? C11 C9 C10 C1 69.3(3) ? C8 C9 C10 C15 66.6(3) ? C11 C9 C10 C15 -51.8(3) ? C8 C9 C10 C5 -55.4(3) y C11 C9 C10 C5 -173.8(2) ? C6 C5 C10 C1 178.4(2) ? C4 C5 C10 C1 -49.4(3) y C6 C5 C10 C15 -57.5(3) ? C4 C5 C10 C15 74.7(3) ? C6 C5 C10 C9 62.9(3) y C4 C5 C10 C9 -164.9(2) ? C12 O1 C11 C9 -17.0(3) y C8 C9 C11 O1 20.2(3) y C10 C9 C11 O1 142.9(2) ? C11 O1 C12 O2 -173.0(2) ? C11 O1 C12 C8 6.0(3) y C7 C8 C12 O2 13.2(5) ? C9 C8 C12 O2 -173.5(3) ? C7 C8 C12 O1 -165.6(3) ? C9 C8 C12 O1 7.6(3) y C3 O3 C16 O4 -2.5(4) ? C3 O3 C16 C17 177.2(2) ?