data_abc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 O7' _chemical_formula_sum 'C20 H20 O7' _chemical_formula_weight 372.36 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 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.364(4) _cell_length_b 7.917(3) _cell_length_c 21.513(6) _cell_angle_alpha 90.00 _cell_angle_beta 127.540(18) _cell_angle_gamma 90.00 _cell_volume 1804.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1461 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 21.18 _exptl_crystal_description 'PLATE' _exptl_crystal_colour 'YELLOW' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type 'MULTI-SCAN' _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details 'SADABS,(BRUKER,2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 ? _diffrn_reflns_number 13682 _diffrn_reflns_av_R_equivalents 0.1291 _diffrn_reflns_av_sigmaI/netI 0.1102 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3173 _reflns_number_gt 2115 _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^)+(0.0552P)^2^+2.2007P] 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 CONSTR _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3173 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.2077 _refine_ls_wR_factor_gt 0.1863 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _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 O1 O 0.6747(2) 0.3340(4) 0.43226(15) 0.0283(7) Uani 1 1 d . . . O2 O 0.4358(3) 0.4588(4) 0.31251(18) 0.0474(10) Uani 1 1 d . . . H2 H 0.3639 0.4970 0.2840 0.071 Uiso 1 1 d R . . O3 O 0.2515(3) 0.4382(4) 0.33089(18) 0.0474(9) Uani 1 1 d . . . O4 O 0.7824(3) 0.1033(5) 0.3151(2) 0.0633(12) Uani 1 1 d . . . O5 O 1.0052(3) 0.2028(4) 0.39043(19) 0.0495(10) Uani 1 1 d . . . H5 H 0.9408 0.1537 0.3552 0.074 Uiso 1 1 d R . . O6 O 1.2104(3) 0.3274(4) 0.52046(19) 0.0449(9) Uani 1 1 d . . . H6A H 1.2629 0.3821 0.5598 0.067 Uiso 1 1 d R . . O7 O 1.2210(3) 0.3926(5) 0.64546(18) 0.0507(10) Uani 1 1 d . . . C1 C 0.7752(4) 0.2558(5) 0.5018(2) 0.0286(10) Uani 1 1 d . . . C2 C 0.7412(4) 0.2046(5) 0.5469(2) 0.0271(10) Uani 1 1 d . . . C3 C 0.6100(4) 0.2513(5) 0.5043(2) 0.0256(10) Uani 1 1 d . . . C4 C 0.5755(4) 0.3266(5) 0.4358(2) 0.0288(10) Uani 1 1 d . . . C5 C 0.5195(4) 0.2364(5) 0.5181(2) 0.0293(10) Uani 1 1 d . . . C6 C 0.3996(4) 0.2984(6) 0.4591(3) 0.0332(11) Uani 1 1 d . . . H6 H 0.3373 0.2900 0.4658 0.040 Uiso 1 1 calc R . . C7 C 0.3685(4) 0.3724(6) 0.3905(2) 0.0325(11) Uani 1 1 d . . . C8 C 0.1523(4) 0.4126(7) 0.3360(3) 0.0538(15) Uani 1 1 d . . . H8A H 0.1762 0.4564 0.3850 0.081 Uiso 1 1 calc R . . H8B H 0.1351 0.2939 0.3329 0.081 Uiso 1 1 calc R . . H8C H 0.0781 0.4701 0.2935 0.081 Uiso 1 1 calc R . . C9 C 0.4561(4) 0.3875(6) 0.3766(2) 0.0300(10) Uani 1 1 d . . . C10 C 0.8910(4) 0.2504(5) 0.5085(2) 0.0296(10) Uani 1 1 d . . . C11 C 0.8898(4) 0.1998(5) 0.4439(2) 0.0304(10) Uani 1 1 d . . . C12 C 0.7848(4) 0.1132(6) 0.3736(3) 0.0363(11) Uani 1 1 d . . . C13 C 0.6832(4) 0.0225(6) 0.3697(3) 0.0399(12) Uani 1 1 d . . . H13A H 0.6665 -0.0837 0.3435 0.060 Uiso 1 1 calc R . . H13B H 0.6079 0.0898 0.3412 0.060 Uiso 1 1 calc R . . H13C H 0.7099 0.0030 0.4218 0.060 Uiso 1 1 calc R . . C14 C 1.0000(4) 0.2343(5) 0.4499(3) 0.0325(11) Uani 1 1 d . . . C15 C 1.1080(4) 0.2981(6) 0.5185(3) 0.0329(11) Uani 1 1 d . . . C16 C 1.1085(4) 0.3326(6) 0.5818(3) 0.0334(11) Uani 1 1 d . . . C17 C 1.0008(4) 0.3113(6) 0.5765(3) 0.0345(11) Uani 1 1 d . . . H17 H 1.0022 0.3382 0.6191 0.041 Uiso 1 1 calc R . . C18 C 1.2354(5) 0.4272(9) 0.7156(3) 0.0685(18) Uani 1 1 d . . . H18A H 1.2178 0.3268 0.7324 0.103 Uiso 1 1 calc R . . H18B H 1.1777 0.5148 0.7058 0.103 Uiso 1 1 calc R . . H18C H 1.3203 0.4632 0.7558 0.103 Uiso 1 1 calc R . . C19 C 0.8228(4) 0.1132(7) 0.6231(3) 0.0448(13) Uani 1 1 d . . . H19A H 0.8980 0.0752 0.6311 0.067 Uiso 1 1 calc R . . H19B H 0.7778 0.0177 0.6224 0.067 Uiso 1 1 calc R . . H19C H 0.8450 0.1879 0.6649 0.067 Uiso 1 1 calc R . . C20 C 0.5483(5) 0.1609(6) 0.5915(3) 0.0433(13) Uani 1 1 d . . . H20A H 0.4772 0.1761 0.5917 0.065 Uiso 1 1 calc R . . H20B H 0.6208 0.2158 0.6365 0.065 Uiso 1 1 calc R . . H20C H 0.5653 0.0424 0.5933 0.065 Uiso 1 1 calc R . . 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 O1 0.0232(15) 0.0374(17) 0.0255(16) 0.0036(13) 0.0156(14) 0.0038(13) O2 0.039(2) 0.072(2) 0.0336(19) 0.0202(18) 0.0231(16) 0.0170(17) O3 0.0266(18) 0.074(2) 0.044(2) 0.0131(18) 0.0223(16) 0.0111(16) O4 0.054(2) 0.107(3) 0.040(2) -0.033(2) 0.0344(19) -0.036(2) O5 0.050(2) 0.068(2) 0.051(2) -0.0199(19) 0.0416(19) -0.0168(18) O6 0.0309(18) 0.058(2) 0.053(2) -0.0079(18) 0.0296(17) -0.0094(16) O7 0.0282(19) 0.075(3) 0.035(2) -0.0106(18) 0.0122(16) -0.0113(17) C1 0.021(2) 0.038(3) 0.022(2) 0.001(2) 0.010(2) 0.0044(19) C2 0.027(2) 0.031(2) 0.022(2) -0.0010(19) 0.014(2) 0.0007(18) C3 0.027(2) 0.029(2) 0.021(2) -0.0043(18) 0.0140(19) -0.0006(18) C4 0.025(2) 0.037(3) 0.030(2) -0.002(2) 0.020(2) 0.0011(19) C5 0.033(3) 0.031(2) 0.031(2) -0.005(2) 0.023(2) -0.0032(19) C6 0.028(2) 0.041(3) 0.040(3) -0.007(2) 0.026(2) -0.005(2) C7 0.025(2) 0.042(3) 0.029(3) 0.000(2) 0.016(2) 0.005(2) C8 0.029(3) 0.072(4) 0.061(4) -0.002(3) 0.027(3) 0.001(3) C9 0.029(2) 0.038(3) 0.026(2) 0.002(2) 0.018(2) 0.0034(19) C10 0.030(2) 0.032(2) 0.034(3) -0.001(2) 0.023(2) 0.003(2) C11 0.027(2) 0.031(2) 0.033(3) -0.002(2) 0.019(2) 0.0008(19) C12 0.036(3) 0.040(3) 0.037(3) -0.001(2) 0.024(2) -0.003(2) C13 0.036(3) 0.040(3) 0.041(3) -0.009(2) 0.022(2) -0.008(2) C14 0.038(3) 0.034(3) 0.035(3) -0.002(2) 0.027(2) 0.002(2) C15 0.028(2) 0.036(3) 0.040(3) 0.002(2) 0.023(2) 0.001(2) C16 0.026(2) 0.035(3) 0.032(3) -0.002(2) 0.014(2) 0.001(2) C17 0.028(2) 0.046(3) 0.025(2) -0.003(2) 0.014(2) 0.003(2) C18 0.053(4) 0.097(5) 0.033(3) -0.011(3) 0.014(3) -0.011(3) C19 0.038(3) 0.059(3) 0.038(3) 0.014(3) 0.024(2) 0.010(2) C20 0.050(3) 0.047(3) 0.047(3) 0.010(2) 0.037(3) 0.001(2) _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 O1 C4 1.376(5) . ? O1 C1 1.406(5) . ? O2 C9 1.355(5) . ? O2 H2 0.8201 . ? O3 C7 1.385(5) . ? O3 C8 1.409(5) . ? O4 C12 1.243(5) . ? O5 C14 1.346(5) . ? O5 H5 0.8201 . ? O6 C15 1.363(5) . ? O6 H6A 0.8200 . ? O7 C16 1.361(5) . ? O7 C18 1.426(6) . ? C1 C2 1.359(6) . ? C1 C10 1.465(6) . ? C2 C3 1.447(6) . ? C2 C19 1.491(6) . ? C3 C4 1.381(6) . ? C3 C5 1.414(6) . ? C4 C9 1.387(6) . ? C5 C6 1.393(6) . ? C5 C20 1.504(6) . ? C6 C7 1.396(6) . ? C6 H6 0.9300 . ? C7 C9 1.379(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C17 1.382(6) . ? C10 C11 1.438(6) . ? C11 C14 1.424(6) . ? C11 C12 1.463(6) . ? C12 C13 1.491(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.386(6) . ? C15 C16 1.384(6) . ? C16 C17 1.384(6) . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C4 O1 C1 104.5(3) . . ? C9 O2 H2 109.5 . . ? C7 O3 C8 117.3(4) . . ? C14 O5 H5 109.5 . . ? C15 O6 H6A 109.4 . . ? C16 O7 C18 119.1(4) . . ? C2 C1 O1 111.9(3) . . ? C2 C1 C10 135.5(4) . . ? O1 C1 C10 112.6(3) . . ? C1 C2 C3 105.9(4) . . ? C1 C2 C19 126.2(4) . . ? C3 C2 C19 127.8(4) . . ? C4 C3 C5 119.1(4) . . ? C4 C3 C2 105.9(3) . . ? C5 C3 C2 135.0(4) . . ? O1 C4 C3 111.8(3) . . ? O1 C4 C9 122.8(4) . . ? C3 C4 C9 125.4(4) . . ? C6 C5 C3 115.9(4) . . ? C6 C5 C20 120.8(4) . . ? C3 C5 C20 123.3(4) . . ? C7 C6 C5 123.1(4) . . ? C7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C9 C7 O3 113.3(4) . . ? C9 C7 C6 121.4(4) . . ? O3 C7 C6 125.3(4) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C7 125.9(4) . . ? O2 C9 C4 119.1(4) . . ? C7 C9 C4 115.0(4) . . ? C17 C10 C11 120.0(4) . . ? C17 C10 C1 118.1(4) . . ? C11 C10 C1 121.6(4) . . ? C14 C11 C10 117.2(4) . . ? C14 C11 C12 118.2(4) . . ? C10 C11 C12 124.6(4) . . ? O4 C12 C11 119.5(4) . . ? O4 C12 C13 116.9(4) . . ? C11 C12 C13 123.5(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 C15 117.2(4) . . ? O5 C14 C11 121.8(4) . . ? C15 C14 C11 121.0(4) . . ? O6 C15 C16 122.2(4) . . ? O6 C15 C14 118.0(4) . . ? C16 C15 C14 119.8(4) . . ? O7 C16 C15 113.5(4) . . ? O7 C16 C17 125.5(4) . . ? C15 C16 C17 120.9(4) . . ? C16 C17 C10 120.7(4) . . ? C16 C17 H17 119.7 . . ? C10 C17 H17 119.7 . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 C19 H19A 109.5 . . ? C2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C5 C20 H20A 109.5 . . ? C5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C2 -0.9(5) . . . . ? C4 O1 C1 C10 179.6(3) . . . . ? O1 C1 C2 C3 0.3(5) . . . . ? C10 C1 C2 C3 179.6(5) . . . . ? O1 C1 C2 C19 178.2(4) . . . . ? C10 C1 C2 C19 -2.5(8) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C19 C2 C3 C4 -177.4(4) . . . . ? C1 C2 C3 C5 -179.3(5) . . . . ? C19 C2 C3 C5 2.8(8) . . . . ? C1 O1 C4 C3 1.2(4) . . . . ? C1 O1 C4 C9 -178.4(4) . . . . ? C5 C3 C4 O1 178.8(4) . . . . ? C2 C3 C4 O1 -1.0(5) . . . . ? C5 C3 C4 C9 -1.7(6) . . . . ? C2 C3 C4 C9 178.5(4) . . . . ? C4 C3 C5 C6 1.0(6) . . . . ? C2 C3 C5 C6 -179.2(4) . . . . ? C4 C3 C5 C20 -178.3(4) . . . . ? C2 C3 C5 C20 1.5(7) . . . . ? C3 C5 C6 C7 -0.5(6) . . . . ? C20 C5 C6 C7 178.8(4) . . . . ? C8 O3 C7 C9 173.5(4) . . . . ? C8 O3 C7 C6 -7.1(7) . . . . ? C5 C6 C7 C9 0.5(7) . . . . ? C5 C6 C7 O3 -178.9(4) . . . . ? O3 C7 C9 O2 0.3(6) . . . . ? C6 C7 C9 O2 -179.2(4) . . . . ? O3 C7 C9 C4 178.5(4) . . . . ? C6 C7 C9 C4 -0.9(6) . . . . ? O1 C4 C9 O2 -0.5(6) . . . . ? C3 C4 C9 O2 180.0(4) . . . . ? O1 C4 C9 C7 -178.9(4) . . . . ? C3 C4 C9 C7 1.6(7) . . . . ? C2 C1 C10 C17 -51.3(7) . . . . ? O1 C1 C10 C17 128.0(4) . . . . ? C2 C1 C10 C11 134.9(5) . . . . ? O1 C1 C10 C11 -45.8(5) . . . . ? C17 C10 C11 C14 -7.3(6) . . . . ? C1 C10 C11 C14 166.3(4) . . . . ? C17 C10 C11 C12 171.5(4) . . . . ? C1 C10 C11 C12 -14.9(7) . . . . ? C14 C11 C12 O4 -14.8(7) . . . . ? C10 C11 C12 O4 166.4(5) . . . . ? C14 C11 C12 C13 160.2(4) . . . . ? C10 C11 C12 C13 -18.6(7) . . . . ? C10 C11 C14 O5 -175.3(4) . . . . ? C12 C11 C14 O5 5.8(6) . . . . ? C10 C11 C14 C15 6.4(6) . . . . ? C12 C11 C14 C15 -172.5(4) . . . . ? O5 C14 C15 O6 1.3(6) . . . . ? C11 C14 C15 O6 179.7(4) . . . . ? O5 C14 C15 C16 -179.8(4) . . . . ? C11 C14 C15 C16 -1.4(7) . . . . ? C18 O7 C16 C15 -177.7(5) . . . . ? C18 O7 C16 C17 4.6(7) . . . . ? O6 C15 C16 O7 -1.9(6) . . . . ? C14 C15 C16 O7 179.3(4) . . . . ? O6 C15 C16 C17 176.0(4) . . . . ? C14 C15 C16 C17 -2.9(7) . . . . ? O7 C16 C17 C10 179.5(4) . . . . ? C15 C16 C17 C10 1.9(7) . . . . ? C11 C10 C17 C16 3.4(7) . . . . ? C1 C10 C17 C16 -170.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.362 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.088