data_20100706aj389 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 O8' _chemical_formula_weight 460.42 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2883(9) _cell_length_b 11.2794(11) _cell_length_c 11.6730(12) _cell_angle_alpha 62.3560(10) _cell_angle_beta 89.0080(10) _cell_angle_gamma 89.8930(10) _cell_volume 1083.15(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 3905 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 28.47 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 5138 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3721 _reflns_number_gt 3373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.2916P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3721 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.27133(15) 0.74856(13) 0.25280(12) 0.0261(3) Uani 1 1 d . . . C2 C 0.16720(17) 0.82331(15) 0.27770(14) 0.0342(3) Uani 1 1 d . . . C3 C 0.04667(18) 0.86754(16) 0.20150(15) 0.0385(4) Uani 1 1 d . . . C4 C 0.02988(17) 0.83819(15) 0.09934(14) 0.0374(4) Uani 1 1 d . . . C5 C 0.13411(17) 0.76762(15) 0.07230(14) 0.0364(3) Uani 1 1 d . . . C6 C 0.25529(16) 0.72144(14) 0.14937(13) 0.0316(3) Uani 1 1 d . . . C7 C 0.26096(15) 0.37570(14) 0.61461(13) 0.0286(3) Uani 1 1 d . . . C8 C 0.34046(14) 0.59672(13) 0.47566(12) 0.0257(3) Uani 1 1 d . . . C9 C 0.39868(15) 0.69315(13) 0.34102(13) 0.0262(3) Uani 1 1 d . . . C10 C 0.51465(15) 0.79007(13) 0.34503(14) 0.0291(3) Uani 1 1 d . . . C11 C 0.61951(15) 0.71059(13) 0.30385(13) 0.0281(3) Uani 1 1 d . . . C12 C 0.52318(18) 0.92605(15) 0.23034(16) 0.0391(4) Uani 1 1 d . . . C13 C 0.61564(18) 0.92328(15) 0.14599(16) 0.0415(4) Uani 1 1 d . . . C15 C 0.34270(16) 0.32245(15) 0.28181(14) 0.0328(3) Uani 1 1 d . . . C16 C 0.46641(17) 0.36661(15) 0.20648(14) 0.0363(3) Uani 1 1 d . . . C17 C 0.48741(17) 0.34002(15) 0.10253(14) 0.0363(3) Uani 1 1 d . . . C18 C 0.38297(17) 0.27234(15) 0.07284(14) 0.0366(3) Uani 1 1 d . . . C19 C 0.25837(16) 0.22658(14) 0.14914(13) 0.0320(3) Uani 1 1 d . . . C20 C 0.23865(15) 0.25049(13) 0.25469(12) 0.0264(3) Uani 1 1 d . . . C21 C 0.23461(15) -0.12545(14) 0.61326(13) 0.0287(3) Uani 1 1 d . . . C22 C 0.16043(14) 0.09636(13) 0.47688(12) 0.0264(3) Uani 1 1 d . . . C23 C 0.10783(15) 0.19440(13) 0.34297(13) 0.0265(3) Uani 1 1 d . . . C24 C -0.00828(15) 0.29028(13) 0.34946(14) 0.0288(3) Uani 1 1 d . . . C25 C -0.11180(15) 0.21254(13) 0.30625(13) 0.0283(3) Uani 1 1 d . . . C26 C -0.01280(18) 0.42770(15) 0.23733(16) 0.0383(4) Uani 1 1 d . . . C27 C -0.10248(18) 0.42757(15) 0.15219(16) 0.0408(4) Uani 1 1 d . . . H1 H 0.1816(18) 0.8429(17) 0.3502(17) 0.041(4) Uiso 1 1 d . . . H2 H -0.026(2) 0.9150(18) 0.2198(16) 0.043(5) Uiso 1 1 d . . . H3 H -0.055(2) 0.8667(18) 0.0490(17) 0.046(5) Uiso 1 1 d . . . H4 H 0.1254(19) 0.7510(18) 0.0013(18) 0.046(5) Uiso 1 1 d . . . H5 H 0.3268(19) 0.6709(18) 0.1323(16) 0.041(4) Uiso 1 1 d . . . H6 H 0.1903(18) 0.3235(17) 0.5967(16) 0.037(4) Uiso 1 1 d . . . H7 H 0.2136(17) 0.4229(16) 0.6576(15) 0.032(4) Uiso 1 1 d . . . H8 H 0.5238(17) 0.7869(16) 0.4292(16) 0.035(4) Uiso 1 1 d . . . H9 H 0.470(2) 1.000(2) 0.2213(18) 0.048(5) Uiso 1 1 d . . . H10 H 0.648(2) 0.992(2) 0.0621(19) 0.056(5) Uiso 1 1 d . . . H11 H 0.3282(18) 0.3410(17) 0.3537(17) 0.042(4) Uiso 1 1 d . . . H12 H 0.539(2) 0.4142(18) 0.2254(17) 0.044(5) Uiso 1 1 d . . . H13 H 0.5743(18) 0.3691(16) 0.0517(16) 0.035(4) Uiso 1 1 d . . . H14 H 0.3968(18) 0.2572(17) -0.0006(17) 0.042(4) Uiso 1 1 d . . . H15 H 0.1858(18) 0.1781(17) 0.1304(16) 0.036(4) Uiso 1 1 d . . . H16 H 0.2821(17) -0.0811(16) 0.6568(15) 0.034(4) Uiso 1 1 d . . . H17 H 0.3055(17) -0.1770(16) 0.5933(14) 0.028(4) Uiso 1 1 d . . . H18 H -0.0233(17) 0.2848(16) 0.4335(16) 0.033(4) Uiso 1 1 d . . . H19 H 0.040(2) 0.502(2) 0.2299(18) 0.050(5) Uiso 1 1 d . . . H20 H -0.1330(19) 0.4981(19) 0.0701(18) 0.046(5) Uiso 1 1 d . . . O1 O 0.32143(10) 0.47262(9) 0.49090(9) 0.0275(2) Uani 1 1 d . . . O2 O 0.30863(12) 0.63276(10) 0.55471(9) 0.0352(3) Uani 1 1 d . . . O3 O 0.50466(10) 0.63193(9) 0.29216(9) 0.0281(2) Uani 1 1 d . . . O4 O 0.68189(11) 0.80064(10) 0.18197(9) 0.0369(3) Uani 1 1 d . . . O5 O 0.17902(10) -0.02725(9) 0.49043(9) 0.0280(2) Uani 1 1 d . . . O6 O 0.18931(12) 0.13090(10) 0.55690(9) 0.0358(3) Uani 1 1 d . . . O7 O 0.00359(10) 0.13500(9) 0.29247(9) 0.0290(2) Uani 1 1 d . . . O8 O -0.16953(12) 0.30516(11) 0.18525(9) 0.0375(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0333(7) 0.0199(6) 0.0235(6) -0.0087(5) -0.0001(5) -0.0029(5) C2 0.0435(8) 0.0326(8) 0.0288(7) -0.0162(6) -0.0029(6) 0.0040(6) C3 0.0399(9) 0.0357(8) 0.0372(8) -0.0147(7) -0.0031(6) 0.0081(7) C4 0.0400(8) 0.0321(8) 0.0319(8) -0.0078(6) -0.0082(6) -0.0009(6) C5 0.0492(9) 0.0328(8) 0.0268(7) -0.0135(6) -0.0053(6) -0.0057(7) C6 0.0401(8) 0.0280(7) 0.0283(7) -0.0145(6) 0.0004(6) -0.0028(6) C7 0.0327(7) 0.0233(7) 0.0301(7) -0.0128(6) 0.0027(6) -0.0025(6) C8 0.0320(7) 0.0215(6) 0.0267(7) -0.0135(6) -0.0052(5) 0.0041(5) C9 0.0336(7) 0.0212(6) 0.0284(7) -0.0153(5) -0.0003(5) 0.0012(5) C10 0.0357(8) 0.0219(7) 0.0316(7) -0.0140(6) -0.0056(6) 0.0007(6) C11 0.0340(7) 0.0245(7) 0.0265(7) -0.0124(6) 0.0006(5) -0.0048(5) C12 0.0426(9) 0.0213(7) 0.0483(9) -0.0114(7) -0.0104(7) -0.0014(6) C13 0.0463(9) 0.0275(8) 0.0376(8) -0.0036(7) -0.0078(7) -0.0077(7) C15 0.0416(8) 0.0319(8) 0.0280(7) -0.0167(6) 0.0026(6) -0.0034(6) C16 0.0385(8) 0.0339(8) 0.0344(8) -0.0140(6) 0.0011(6) -0.0060(6) C17 0.0388(8) 0.0325(8) 0.0310(8) -0.0094(6) 0.0072(6) 0.0003(6) C18 0.0487(9) 0.0354(8) 0.0267(7) -0.0156(6) 0.0061(6) 0.0023(7) C19 0.0398(8) 0.0300(7) 0.0296(7) -0.0166(6) 0.0002(6) -0.0001(6) C20 0.0336(7) 0.0199(6) 0.0244(6) -0.0093(5) 0.0011(5) 0.0027(5) C21 0.0327(7) 0.0239(7) 0.0309(7) -0.0140(6) -0.0022(6) 0.0010(6) C22 0.0328(7) 0.0220(7) 0.0276(7) -0.0144(6) 0.0054(5) -0.0050(5) C23 0.0346(7) 0.0222(6) 0.0278(7) -0.0159(5) 0.0014(5) -0.0023(5) C24 0.0352(8) 0.0228(7) 0.0310(7) -0.0150(6) 0.0060(6) -0.0025(6) C25 0.0352(7) 0.0246(7) 0.0261(7) -0.0126(6) -0.0008(5) 0.0033(5) C26 0.0431(9) 0.0220(7) 0.0448(9) -0.0117(7) 0.0110(7) 0.0008(6) C27 0.0458(9) 0.0277(8) 0.0362(8) -0.0044(7) 0.0090(7) 0.0049(7) O1 0.0372(5) 0.0212(5) 0.0267(5) -0.0132(4) 0.0002(4) -0.0007(4) O2 0.0544(6) 0.0261(5) 0.0300(5) -0.0172(4) 0.0034(4) 0.0019(4) O3 0.0314(5) 0.0273(5) 0.0322(5) -0.0193(4) 0.0012(4) -0.0012(4) O4 0.0430(6) 0.0330(6) 0.0282(5) -0.0087(4) 0.0024(4) -0.0068(5) O5 0.0375(6) 0.0211(5) 0.0279(5) -0.0136(4) 0.0009(4) -0.0007(4) O6 0.0563(7) 0.0259(5) 0.0297(5) -0.0167(4) -0.0030(4) -0.0028(4) O7 0.0320(5) 0.0289(5) 0.0331(5) -0.0204(4) 0.0000(4) -0.0003(4) O8 0.0447(6) 0.0342(6) 0.0281(5) -0.0098(4) -0.0020(4) 0.0049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3866(19) . ? C1 C2 1.395(2) . ? C1 C9 1.5140(19) . ? C2 C3 1.383(2) . ? C2 H1 0.980(17) . ? C3 C4 1.389(2) . ? C3 H2 0.939(18) . ? C4 C5 1.375(2) . ? C4 H3 0.956(19) . ? C5 C6 1.395(2) . ? C5 H4 0.935(18) . ? C6 H5 0.951(18) . ? C7 O1 1.4510(16) . ? C7 C11 1.503(2) 2_666 ? C7 H6 0.970(17) . ? C7 H7 0.984(16) . ? C8 O2 1.2009(16) . ? C8 O1 1.3383(16) . ? C8 C9 1.5271(18) . ? C9 O3 1.4542(16) . ? C9 C10 1.5528(18) . ? C10 C12 1.498(2) . ? C10 C11 1.5374(19) . ? C10 H8 0.971(17) . ? C11 O4 1.4228(16) . ? C11 O3 1.4369(16) . ? C11 C7 1.503(2) 2_666 ? C12 C13 1.307(3) . ? C12 H9 0.93(2) . ? C13 O4 1.391(2) . ? C13 H10 0.97(2) . ? C15 C16 1.379(2) . ? C15 C20 1.395(2) . ? C15 H11 0.962(18) . ? C16 C17 1.389(2) . ? C16 H12 0.954(18) . ? C17 C18 1.380(2) . ? C17 H13 0.957(17) . ? C18 C19 1.392(2) . ? C18 H14 0.956(17) . ? C19 C20 1.3874(19) . ? C19 H15 0.959(17) . ? C20 C23 1.5143(19) . ? C21 O5 1.4488(17) . ? C21 C25 1.503(2) 2_556 ? C21 H16 0.974(16) . ? C21 H17 0.972(16) . ? C22 O6 1.2012(16) . ? C22 O5 1.3395(16) . ? C22 C23 1.5249(19) . ? C23 O7 1.4569(15) . ? C23 C24 1.5516(19) . ? C24 C26 1.495(2) . ? C24 C25 1.5421(19) . ? C24 H18 0.961(16) . ? C25 O8 1.4243(17) . ? C25 O7 1.4355(16) . ? C25 C21 1.503(2) 2_556 ? C26 C27 1.308(3) . ? C26 H19 0.93(2) . ? C27 O8 1.3942(19) . ? C27 H20 0.966(19) . ? 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_3 _geom_angle_publ_flag C6 C1 C2 119.71(13) . . ? C6 C1 C9 120.08(12) . . ? C2 C1 C9 120.18(12) . . ? C3 C2 C1 120.20(14) . . ? C3 C2 H1 121.4(10) . . ? C1 C2 H1 118.4(10) . . ? C2 C3 C4 119.87(15) . . ? C2 C3 H2 120.6(11) . . ? C4 C3 H2 119.5(11) . . ? C5 C4 C3 120.12(14) . . ? C5 C4 H3 120.7(11) . . ? C3 C4 H3 119.2(11) . . ? C4 C5 C6 120.41(14) . . ? C4 C5 H4 120.5(11) . . ? C6 C5 H4 119.1(11) . . ? C1 C6 C5 119.65(14) . . ? C1 C6 H5 119.5(10) . . ? C5 C6 H5 120.8(10) . . ? O1 C7 C11 108.64(11) . 2_666 ? O1 C7 H6 106.9(10) . . ? C11 C7 H6 111.5(10) 2_666 . ? O1 C7 H7 109.5(9) . . ? C11 C7 H7 110.4(9) 2_666 . ? H6 C7 H7 109.7(13) . . ? O2 C8 O1 124.99(12) . . ? O2 C8 C9 122.38(12) . . ? O1 C8 C9 112.50(10) . . ? O3 C9 C1 112.63(10) . . ? O3 C9 C8 112.86(10) . . ? C1 C9 C8 107.73(11) . . ? O3 C9 C10 90.88(10) . . ? C1 C9 C10 119.82(11) . . ? C8 C9 C10 112.27(11) . . ? C12 C10 C11 101.53(12) . . ? C12 C10 C9 116.35(12) . . ? C11 C10 C9 84.60(9) . . ? C12 C10 H8 116.2(10) . . ? C11 C10 H8 119.8(10) . . ? C9 C10 H8 114.0(10) . . ? O4 C11 O3 112.48(10) . . ? O4 C11 C7 107.00(11) . 2_666 ? O3 C11 C7 111.77(11) . 2_666 ? O4 C11 C10 107.98(11) . . ? O3 C11 C10 92.17(10) . . ? C7 C11 C10 124.86(12) 2_666 . ? C13 C12 C10 109.04(14) . . ? C13 C12 H9 126.0(11) . . ? C10 C12 H9 124.9(11) . . ? C12 C13 O4 115.33(14) . . ? C12 C13 H10 131.9(12) . . ? O4 C13 H10 112.8(12) . . ? C16 C15 C20 120.38(13) . . ? C16 C15 H11 119.9(10) . . ? C20 C15 H11 119.8(10) . . ? C15 C16 C17 119.93(14) . . ? C15 C16 H12 121.1(11) . . ? C17 C16 H12 119.0(11) . . ? C18 C17 C16 119.98(14) . . ? C18 C17 H13 120.3(9) . . ? C16 C17 H13 119.7(9) . . ? C17 C18 C19 120.33(14) . . ? C17 C18 H14 119.4(10) . . ? C19 C18 H14 120.3(10) . . ? C20 C19 C18 119.75(14) . . ? C20 C19 H15 119.1(10) . . ? C18 C19 H15 121.1(10) . . ? C19 C20 C15 119.59(13) . . ? C19 C20 C23 120.28(12) . . ? C15 C20 C23 120.09(11) . . ? O5 C21 C25 108.51(11) . 2_556 ? O5 C21 H16 110.3(10) . . ? C25 C21 H16 111.5(9) 2_556 . ? O5 C21 H17 106.3(9) . . ? C25 C21 H17 111.3(9) 2_556 . ? H16 C21 H17 108.9(13) . . ? O6 C22 O5 124.95(13) . . ? O6 C22 C23 122.30(12) . . ? O5 C22 C23 112.61(10) . . ? O7 C23 C20 112.48(10) . . ? O7 C23 C22 112.97(10) . . ? C20 C23 C22 107.83(11) . . ? O7 C23 C24 90.89(10) . . ? C20 C23 C24 120.07(11) . . ? C22 C23 C24 111.94(11) . . ? C26 C24 C25 101.74(12) . . ? C26 C24 C23 116.66(11) . . ? C25 C24 C23 84.59(9) . . ? C26 C24 H18 115.9(10) . . ? C25 C24 H18 118.4(9) . . ? C23 C24 H18 115.0(10) . . ? O8 C25 O7 112.66(10) . . ? O8 C25 C21 106.96(12) . 2_556 ? O7 C25 C21 111.81(11) . 2_556 ? O8 C25 C24 107.74(11) . . ? O7 C25 C24 92.09(10) . . ? C21 C25 C24 125.01(11) 2_556 . ? C27 C26 C24 109.00(14) . . ? C27 C26 H19 125.7(12) . . ? C24 C26 H19 125.3(12) . . ? C26 C27 O8 115.35(14) . . ? C26 C27 H20 131.6(11) . . ? O8 C27 H20 113.1(11) . . ? C8 O1 C7 116.09(10) . . ? C11 O3 C9 92.00(9) . . ? C13 O4 C11 106.02(11) . . ? C22 O5 C21 116.16(10) . . ? C25 O7 C23 92.08(9) . . ? C27 O8 C25 106.08(11) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.216 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.039