#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006946.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_2006946 loop_ _publ_author_name 'Kakuda, H.' 'Helal, A. M.' 'Nakamura, N.' 'Hattori, M.' _publ_section_title ; 8\a-Hydroxy-11\a,13-dihydrozaluzanin C ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 113 _journal_page_last 114 _journal_volume 54 _journal_year 1998 _chemical_formula_iupac 'C15 H20 O4 ' _chemical_formula_moiety 'C15 H20 O4 ' _chemical_formula_sum 'C15 H20 O4' _chemical_formula_weight 264.32 _chemical_melting_point 442 _chemical_name_common ' 8\a-Hydroxy-11\a,13-dihydrozaluzanin C' _chemical_name_systematic ; Decahydro-4,8-dihydroxy-3-methyl-6,9- bis(methylene)-azuleno[4,5-b]furan-2(3H)-one ; _space_group_IT_number 145 _symmetry_cell_setting trigonal _symmetry_space_group_name_Hall 'P 32' _symmetry_space_group_name_H-M 'P 32' _audit_creation_method SHELXL _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 9.221(4) _cell_length_b 9.221(4) _cell_length_c 14.006(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 12.0 _cell_measurement_theta_min 10.2 _cell_volume 1031.3(8) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics ' ORTEPII (Johnson, 1976), CHARON (Lauher, 1989)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1780 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.55 _diffrn_standards_decay_% 0.68 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 426.00 _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.310 _exptl_crystal_size_min 0.170 _refine_diff_density_max 0.156 _refine_diff_density_min -0.161 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.920 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 172 _refine_ls_number_reflns 1636 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.919 _refine_ls_restrained_S_obs 0.925 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max -0.011 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ;w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1466 _refine_ls_wR_factor_ref 0.1211 _reflns_number_gt 1150 _reflns_number_total 1636 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1327.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 32 ' _[local]_cod_cif_authors_sg_Hall 'P 32 ' _[local]_cod_chemical_formula_sum_orig 'C15 H20 O4 ' _cod_original_cell_volume 1031.4(9) _cod_database_code 2006946 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -y, +x-y, 2/3+z' ' -x+y, -x, 1/3+z' loop_ _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_occupancy O3 1.2639(5) 0.6758(5) 0.1951(2) 0.0642(10) Uani d 1.00 O6 0.7788(3) 0.5767(4) 0.2761(2) 0.0449(7) Uani d 1.00 O8 0.4406(3) 0.6381(4) 0.0495(2) 0.0439(7) Uani d 1.00 O12 0.5726(5) 0.4177(6) 0.3770(2) 0.0778(13) Uani d 1.00 C1 1.0087(5) 0.7947(5) 0.0520(3) 0.0389(9) Uani d 1.00 C2 1.1192(6) 0.7159(6) 0.0575(3) 0.0485(11) Uani d 1.00 C3 1.2186(5) 0.7854(6) 0.1486(3) 0.0470(10) Uani d 1.00 C4 1.1068(5) 0.8195(5) 0.2134(3) 0.0390(9) Uani d 1.00 C5 0.9530(5) 0.7908(5) 0.1581(3) 0.0346(8) Uani d 1.00 C6 0.7928(4) 0.6239(5) 0.1759(3) 0.0311(7) Uani d 1.00 C7 0.6309(5) 0.6272(5) 0.1570(3) 0.0333(8) Uani d 1.00 C8 0.5838(5) 0.6166(5) 0.0518(2) 0.0344(8) Uani d 1.00 C9 0.7250(5) 0.7522(6) -0.0087(3) 0.0429(9) Uani d 1.00 C10 0.8709(6) 0.7215(6) -0.0218(3) 0.0453(10) Uani d 1.00 C11 0.5045(5) 0.4902(5) 0.2235(3) 0.0372(8) Uani d 1.00 C12 0.6154(5) 0.4881(6) 0.3017(3) 0.0446(9) Uani d 1.00 C13 0.4016(6) 0.3150(5) 0.1818(4) 0.0549(12) Uani d 1.00 C14 0.8744(8) 0.6362(9) -0.0947(4) 0.072(2) Uani d 1.00 C15 1.1461(5) 0.8793(6) 0.3001(4) 0.0508(11) Uani d 1.00 H1 1.0713 0.8912 0.0362 0.0431 Uiso d 1.00 H2a 1.0590 0.6026 0.0622 0.0494 Uiso d 1.00 H2b 1.1861 0.7216 0.0025 0.0494 Uiso d 1.00 H3 1.3297 0.8839 0.1285 0.0532 Uiso d 1.00 H5 0.9348 0.8893 0.1760 0.0355 Uiso d 1.00 H6 0.7947 0.5374 0.1417 0.0329 Uiso d 1.00 H7 0.6539 0.7330 0.1785 0.0342 Uiso d 1.00 H8 0.5525 0.5056 0.0288 0.0355 Uiso d 1.00 H9a 0.7698 0.8712 0.0215 0.0443 Uiso d 1.00 H9b 0.6945 0.7628 -0.0695 0.0443 Uiso d 1.00 H11 0.4260 0.5098 0.2557 0.0393 Uiso d 1.00 H13a 0.3282 0.2273 0.2316 0.0570 Uiso d 1.00 H13b 0.4750 0.2884 0.1514 0.0570 Uiso d 1.00 H13c 0.3244 0.3240 0.1395 0.0570 Uiso d 1.00 H14a 0.9462 0.6053 -0.1043 0.0735 Uiso d 1.00 H14b 0.7846 0.5726 -0.1434 0.0735 Uiso d 1.00 H15a 1.0735 0.9046 0.3434 0.0532 Uiso d 1.00 H15b 1.2483 0.8922 0.3311 0.0532 Uiso d 1.00 H30 1.2997 0.6331 0.1473 0.0646 Uiso d 1.00 H80 0.4085 0.6212 -0.0106 0.0443 Uiso d 1.00 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 O3 0.078(2) 0.110(3) 0.044(2) 0.076(2) 0.021(2) 0.024(2) O6 0.041(2) 0.055(2) 0.0327(14) 0.0195(14) 0.0000(12) 0.0124(13) O8 0.043(2) 0.067(2) 0.0329(14) 0.0361(14) -0.0068(12) -0.0058(13) O12 0.054(2) 0.109(3) 0.040(2) 0.018(2) 0.005(2) 0.030(2) C1 0.041(2) 0.041(2) 0.038(2) 0.022(2) 0.011(2) 0.016(2) C2 0.056(3) 0.071(3) 0.040(2) 0.047(2) 0.020(2) 0.017(2) C3 0.038(2) 0.059(3) 0.049(2) 0.027(2) 0.011(2) 0.016(2) C4 0.036(2) 0.036(2) 0.045(2) 0.017(2) 0.004(2) 0.006(2) C5 0.036(2) 0.037(2) 0.036(2) 0.022(2) 0.001(2) 0.002(2) C6 0.035(2) 0.034(2) 0.026(2) 0.019(2) 0.0031(14) 0.0035(14) C7 0.038(2) 0.038(2) 0.027(2) 0.022(2) 0.003(2) 0.0021(15) C8 0.039(2) 0.040(2) 0.031(2) 0.025(2) -0.001(2) -0.003(2) C9 0.047(2) 0.056(2) 0.031(2) 0.030(2) 0.002(2) 0.012(2) C10 0.046(2) 0.057(3) 0.037(2) 0.028(2) 0.011(2) 0.014(2) C11 0.035(2) 0.045(2) 0.031(2) 0.019(2) 0.005(2) 0.000(2) C12 0.041(2) 0.049(2) 0.039(2) 0.019(2) 0.006(2) 0.010(2) C13 0.054(3) 0.040(2) 0.053(3) 0.011(2) 0.002(2) -0.002(2) C14 0.076(4) 0.111(5) 0.048(3) 0.060(4) 0.007(3) -0.013(3) C15 0.041(2) 0.054(3) 0.062(3) 0.028(2) -0.006(2) -0.008(2) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.0106 0.0060 ;International Tables for Crystallography (1992, 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 2 0 -1 2 0 1 2 -1 1 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 C6 O6 C12 109.9(3) no C2 C1 C5 103.3(3) yes C2 C1 C10 115.9(4) yes C5 C1 C10 116.5(3) yes C1 C2 C3 104.5(4) no O3 C3 C2 114.5(4) yes O3 C3 C4 110.0(3) yes C2 C3 C4 105.1(3) yes C3 C4 C5 109.3(4) no C3 C4 C15 124.6(4) no C5 C4 C15 125.8(4) no C1 C5 C4 102.3(3) yes C1 C5 C6 108.6(3) yes C4 C5 C6 116.1(3) yes O6 C6 C5 110.8(3) yes O6 C6 C7 103.4(3) yes C5 C6 C7 114.4(3) yes C6 C7 C8 114.5(3) yes C6 C7 C11 103.1(3) yes C8 C7 C11 117.3(3) yes O8 C8 C7 105.4(3) yes O8 C8 C9 109.9(3) yes C7 C8 C9 112.5(3) yes C8 C9 C10 112.6(3) no C1 C10 C9 117.3(4) no C1 C10 C14 122.6(4) no C9 C10 C14 120.0(4) no C7 C11 C12 102.2(3) yes C7 C11 C13 117.1(3) yes C12 C11 C13 109.4(4) yes O6 C12 O12 121.7(4) no O6 C12 C11 110.9(3) no O12 C12 C11 127.3(4) no C3 O3 H30 105.4 no C8 O8 H80 104.4 no C2 C1 H1 105.0 no C5 C1 H1 109.2 no C10 C1 H1 106.4 no C1 C2 H2a 112.6 no C1 C2 H2b 119.5 no C3 C2 H2a 108.6 no C3 C2 H2b 114.3 no H2a C2 H2b 97.2 no O3 C3 H3 103.8 no C2 C3 H3 105.8 no C4 C3 H3 117.9 no C1 C5 H5 113.9 no C4 C5 H5 105.7 no C6 C5 H5 110.2 no O6 C6 H6 105.9 no C5 C6 H6 110.7 no C7 C6 H6 111.2 no C6 C7 H7 104.5 no C8 C7 H7 106.6 no C11 C7 H7 110.2 no O8 C8 H8 109.3 no C7 C8 H8 108.3 no C9 C8 H8 111.2 no C8 C9 H9a 111.2 no C8 C9 H9b 114.8 no C10 C9 H9a 108.8 no C10 C9 H9b 104.7 no H9a C9 H9b 104.2 no C7 C11 H11 118.3 no C12 C11 H11 104.2 no C13 C11 H11 104.8 no C11 C13 H13a 113.1 no C11 C13 H13b 107.8 no C11 C13 H13c 103.8 no H13a C13 H13b 112.6 no H13a C13 H13c 105.2 no H13b C13 H13c 114.1 no C10 C14 H14a 125.8 no C10 C14 H14b 128.6 no H14a C14 H14b 104.5 no C4 C15 H15a 125.3 no C4 C15 H15b 120.3 no H15a C15 H15b 114.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O3 C3 1.429(5) no O6 C6 1.457(4) no O6 C12 1.355(5) no O8 C8 1.430(4) no O12 C12 1.197(5) no C1 C2 1.520(6) yes C1 C5 1.566(5) yes C1 C10 1.510(7) yes C2 C3 1.513(7) yes C3 C4 1.519(6) no C4 C5 1.518(6) no C4 C15 1.308(6) no C5 C6 1.529(5) no C6 C7 1.531(5) no C7 C8 1.525(5) no C7 C11 1.533(5) no C8 C9 1.532(5) no C9 C10 1.519(6) yes C10 C14 1.299(7) no C11 C12 1.506(6) no C11 C13 1.523(6) no O3 H30 0.917 no O8 H80 0.880 no C1 H1 0.813 no C2 H2a 0.908 no C2 H2b 0.972 no C3 H3 1.011 no C5 H5 1.034 no C6 H6 0.938 no C7 H7 0.939 no C8 H8 0.969 no C9 H9a 1.049 no C9 H9b 0.917 no C11 H11 0.944 no C13 H13a 1.025 no C13 H13b 0.930 no C13 H13c 0.962 no C14 H14a 0.852 no C14 H14b 1.005 no C15 H15a 1.013 no C15 H15b 0.989 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O3 O8 2.739(5) 1_555 1_655 O8 O3 2.790(5) 1_555 2_654 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H30 O8 1_555 1_555 1_655 0.917 1.873 2.739(5) 156.5 yes O8 H80 O3 1_555 1_555 2_654 0.880 1.912 2.790(5) 175.3 yes 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 O3 C3 C2 C1 149.6(3) no O3 C3 C4 C5 -130.3(4) no O3 C3 C4 C15 55.6(6) no O6 C6 C5 C1 152.7(3) no O6 C6 C5 C4 38.1(5) no O6 C6 C7 C8 -160.8(3) no O6 C6 C7 C11 -32.3(4) yes O6 C12 C11 C7 -12.4(5) yes O6 C12 C11 C13 112.3(4) no O8 C8 C7 C6 -174.5(3) no O8 C8 C7 C11 64.5(4) no O8 C8 C9 C10 -171.2(3) no O12 C12 O6 C6 170.2(5) no O12 C12 C11 C7 168.9(5) no O12 C12 C11 C13 -66.4(6) no C1 C2 C3 C4 28.8(4) yes C1 C5 C4 C3 -17.3(4) yes C1 C5 C4 C15 156.7(4) no C1 C5 C6 C7 -91.0(4) yes C1 C10 C9 C8 -89.4(5) yes C2 C1 C5 C4 34.6(4) yes C2 C1 C5 C6 -88.7(4) no C2 C1 C10 C9 159.9(4) no C2 C1 C10 C14 -20.7(7) no C2 C3 C4 C5 -6.6(4) yes C2 C3 C4 C15 179.3(4) no C3 C2 C1 C5 -39.7(4) yes C3 C2 C1 C10 -168.4(3) no C3 C4 C5 C6 100.7(4) no C4 C5 C1 C10 162.9(3) no C4 C5 C6 C7 154.4(3) no C5 C1 C10 C9 38.0(5) yes C5 C1 C10 C14 -142.5(5) no C5 C6 O6 C12 148.9(3) no C5 C6 C7 C8 78.6(4) yes C5 C6 C7 C11 -152.8(3) no C6 O6 C12 C11 -8.6(5) yes C6 C5 C1 C10 39.6(4) yes C6 C5 C4 C15 -85.3(5) no C6 C7 C8 C9 -54.7(4) yes C6 C7 C11 C12 26.9(4) yes C6 C7 C11 C13 -92.5(4) no C7 C6 O6 C12 25.9(4) yes C7 C8 C9 C10 71.6(4) yes C8 C7 C11 C12 153.7(3) no C8 C7 C11 C13 34.3(5) no C8 C9 C10 C14 91.1(6) no C9 C8 C7 C11 -175.7(3) no