data_cu_qpg39_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 O6' _chemical_formula_sum 'C17 H18 O6' _chemical_formula_weight 318.31 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.10060(10) _cell_length_b 15.0443(2) _cell_length_c 16.0425(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1472.37(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9051 _cell_measurement_theta_min 5.52 _cell_measurement_theta_max 69.14 _exptl_crystal_description 'prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.914 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6333 _exptl_absorpt_correction_T_max 0.8383 _exptl_absorpt_process_details 'sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 9165 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.51 _diffrn_reflns_theta_max 69.53 _reflns_number_total 2682 _reflns_number_gt 2679 _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^)+(0.0381P)^2^+0.3873P] 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 0.0126(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(13) _refine_ls_number_reflns 2682 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 O11' O 0.37823(16) 0.27859(6) 0.62833(6) 0.0203(2) Uani 1 1 d . . . O4 O -0.43515(17) 0.61767(7) 0.37151(6) 0.0232(2) Uani 1 1 d . . . H4 H -0.4112 0.6582 0.3367 0.035 Uiso 1 1 calc R . . O1 O 0.25114(15) 0.57634(6) 0.58922(6) 0.0166(2) Uani 1 1 d . . . O1' O -0.11755(15) 0.39542(6) 0.61075(6) 0.0170(2) Uani 1 1 d . . . O9' O 0.09731(17) 0.77660(6) 0.75990(6) 0.0211(2) Uani 1 1 d . . . H9' H 0.1148 0.8061 0.8038 0.032 Uiso 1 1 calc R . . O10' O 0.34163(17) 0.36381(6) 0.51435(6) 0.0224(2) Uani 1 1 d . . . C11' C 0.3556(3) 0.19958(9) 0.57722(9) 0.0242(3) Uani 1 1 d . . . H11A H 0.2189 0.2030 0.5453 0.036 Uiso 1 1 calc R . . H11B H 0.3525 0.1469 0.6131 0.036 Uiso 1 1 calc R . . H11C H 0.4800 0.1955 0.5388 0.036 Uiso 1 1 calc R . . C10' C 0.3637(2) 0.35592(9) 0.58862(8) 0.0172(3) Uani 1 1 d . . . C3' C 0.3763(2) 0.43427(9) 0.64764(8) 0.0165(3) Uani 1 1 d . . . H3' H 0.5117 0.4680 0.6324 0.020 Uiso 1 1 calc R . . C2' C 0.1820(2) 0.49968(8) 0.63747(8) 0.0152(3) Uani 1 1 d . . . C1' C -0.0202(2) 0.46393(8) 0.59201(8) 0.0153(3) Uani 1 1 d . . . C2 C -0.0723(2) 0.52827(8) 0.52832(8) 0.0162(3) Uani 1 1 d . . . C3 C -0.2505(2) 0.53543(9) 0.47387(8) 0.0171(3) Uani 1 1 d . . . H3 H -0.3625 0.4916 0.4727 0.021 Uiso 1 1 calc R . . C4 C -0.2579(2) 0.60830(8) 0.42190(8) 0.0174(3) Uani 1 1 d . . . C5 C -0.0859(2) 0.67084(8) 0.42282(8) 0.0177(3) Uani 1 1 d . . . H5 H -0.0925 0.7198 0.3856 0.021 Uiso 1 1 calc R . . C6 C 0.0924(2) 0.66370(9) 0.47589(8) 0.0170(3) Uani 1 1 d . . . H6 H 0.2081 0.7059 0.4752 0.020 Uiso 1 1 calc R . . C1 C 0.0937(2) 0.59162(8) 0.53038(8) 0.0154(3) Uani 1 1 d . . . C4' C 0.3925(2) 0.41475(9) 0.74124(8) 0.0190(3) Uani 1 1 d . . . H4'1 H 0.2947 0.3651 0.7573 0.023 Uiso 1 1 calc R . . H4'2 H 0.5448 0.3998 0.7574 0.023 Uiso 1 1 calc R . . C5' C 0.3190(2) 0.50164(9) 0.78134(8) 0.0184(3) Uani 1 1 d . . . H5'1 H 0.4348 0.5476 0.7775 0.022 Uiso 1 1 calc R . . H5'2 H 0.2791 0.4928 0.8406 0.022 Uiso 1 1 calc R . . C6' C 0.1176(2) 0.52705(8) 0.72888(8) 0.0164(3) Uani 1 1 d . . . H6' H -0.0040 0.4866 0.7464 0.020 Uiso 1 1 calc R . . C7' C 0.0299(2) 0.62100(9) 0.73507(8) 0.0175(3) Uani 1 1 d . . . C9' C 0.1821(2) 0.68945(8) 0.77135(9) 0.0189(3) Uani 1 1 d . . . H9'1 H 0.2020 0.6779 0.8316 0.023 Uiso 1 1 calc R . . H9'2 H 0.3272 0.6848 0.7441 0.023 Uiso 1 1 calc R . . C8' C -0.1706(2) 0.64178(10) 0.70936(10) 0.0234(3) Uani 1 1 d . . . H8'1 H -0.2214 0.7013 0.7136 0.028 Uiso 1 1 calc R . . H8'2 H -0.2632 0.5971 0.6867 0.028 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 O11' 0.0253(5) 0.0144(4) 0.0212(5) -0.0021(4) -0.0011(4) 0.0023(4) O4 0.0231(5) 0.0236(5) 0.0228(5) 0.0062(4) -0.0057(4) -0.0022(4) O1 0.0164(4) 0.0153(4) 0.0180(5) 0.0024(4) -0.0014(4) -0.0025(4) O1' 0.0173(4) 0.0142(4) 0.0194(4) 0.0012(3) 0.0002(4) -0.0017(4) O9' 0.0292(5) 0.0144(4) 0.0197(5) -0.0016(4) -0.0010(4) 0.0009(4) O10' 0.0253(5) 0.0233(5) 0.0186(5) -0.0021(4) -0.0001(4) 0.0010(4) C11' 0.0299(7) 0.0170(6) 0.0256(7) -0.0052(6) -0.0010(6) 0.0011(6) C10' 0.0117(6) 0.0198(6) 0.0200(6) -0.0011(5) 0.0009(5) 0.0015(5) C3' 0.0143(6) 0.0156(6) 0.0196(6) 0.0010(5) -0.0015(5) 0.0006(5) C2' 0.0163(6) 0.0123(6) 0.0169(6) 0.0016(5) 0.0009(5) -0.0005(5) C1' 0.0150(6) 0.0151(6) 0.0158(6) -0.0032(5) 0.0032(5) 0.0021(5) C2 0.0177(6) 0.0144(6) 0.0164(6) -0.0015(5) 0.0032(5) 0.0005(5) C3 0.0170(6) 0.0173(6) 0.0170(6) -0.0021(5) 0.0015(5) -0.0023(5) C4 0.0191(6) 0.0184(6) 0.0146(6) -0.0017(5) -0.0002(5) 0.0032(5) C5 0.0237(7) 0.0145(6) 0.0150(6) -0.0001(5) 0.0019(5) 0.0024(5) C6 0.0186(6) 0.0144(6) 0.0180(6) -0.0006(5) 0.0021(5) -0.0025(5) C1 0.0151(6) 0.0161(6) 0.0149(6) -0.0033(5) 0.0003(5) 0.0014(5) C4' 0.0190(6) 0.0187(6) 0.0192(6) -0.0002(5) -0.0024(5) 0.0023(5) C5' 0.0205(6) 0.0174(6) 0.0173(6) -0.0010(5) -0.0013(5) 0.0000(5) C6' 0.0171(6) 0.0163(6) 0.0156(6) -0.0009(5) 0.0007(5) -0.0021(5) C7' 0.0198(6) 0.0177(6) 0.0148(6) -0.0008(5) 0.0023(5) 0.0001(5) C9' 0.0208(6) 0.0150(6) 0.0209(6) -0.0010(5) -0.0016(5) 0.0003(5) C8' 0.0210(7) 0.0193(6) 0.0298(7) -0.0049(6) 0.0005(6) -0.0005(6) _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 O11' C10' 1.3293(16) . ? O11' C11' 1.4506(16) . ? O4 C4 1.3572(16) . ? O4 H4 0.8400 . ? O1 C1 1.3662(16) . ? O1 C2' 1.4517(15) . ? O1' C1' 1.2269(16) . ? O9' C9' 1.4213(16) . ? O9' H9' 0.8400 . ? O10' C10' 1.2050(18) . ? C11' H11A 0.9800 . ? C11' H11B 0.9800 . ? C11' H11C 0.9800 . ? C10' C3' 1.5139(18) . ? C3' C4' 1.5334(18) . ? C3' C2' 1.5492(17) . ? C3' H3' 1.0000 . ? C2' C1' 1.5303(17) . ? C2' C6' 1.5729(17) . ? C1' C2 1.4430(18) . ? C2 C1 1.3910(18) . ? C2 C3 1.3984(19) . ? C3 C4 1.3780(19) . ? C3 H3 0.9500 . ? C4 C5 1.4096(19) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 C1 1.3930(18) . ? C6 H6 0.9500 . ? C4' C5' 1.5244(18) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' C6' 1.5373(18) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' C7' 1.5148(18) . ? C6' H6' 1.0000 . ? C7' C8' 1.328(2) . ? C7' C9' 1.5038(19) . ? C9' H9'1 0.9900 . ? C9' H9'2 0.9900 . ? C8' H8'1 0.9500 . ? C8' H8'2 0.9500 . ? 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 C10' O11' C11' 116.10(10) . . ? C4 O4 H4 109.5 . . ? C1 O1 C2' 107.31(10) . . ? C9' O9' H9' 109.5 . . ? O11' C11' H11A 109.5 . . ? O11' C11' H11B 109.5 . . ? H11A C11' H11B 109.5 . . ? O11' C11' H11C 109.5 . . ? H11A C11' H11C 109.5 . . ? H11B C11' H11C 109.5 . . ? O10' C10' O11' 124.59(12) . . ? O10' C10' C3' 123.18(12) . . ? O11' C10' C3' 112.23(11) . . ? C10' C3' C4' 117.81(11) . . ? C10' C3' C2' 112.96(11) . . ? C4' C3' C2' 105.92(10) . . ? C10' C3' H3' 106.5 . . ? C4' C3' H3' 106.5 . . ? C2' C3' H3' 106.5 . . ? O1 C2' C1' 105.04(10) . . ? O1 C2' C3' 109.77(10) . . ? C1' C2' C3' 116.34(10) . . ? O1 C2' C6' 111.20(10) . . ? C1' C2' C6' 109.59(10) . . ? C3' C2' C6' 105.01(10) . . ? O1' C1' C2 129.08(12) . . ? O1' C1' C2' 124.65(12) . . ? C2 C1' C2' 106.22(11) . . ? C1 C2 C3 121.86(12) . . ? C1 C2 C1' 106.40(12) . . ? C3 C2 C1' 131.70(12) . . ? C4 C3 C2 117.71(12) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? O4 C4 C3 117.99(12) . . ? O4 C4 C5 122.01(12) . . ? C3 C4 C5 120.00(12) . . ? C6 C5 C4 122.63(12) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C1 116.78(12) . . ? C5 C6 H6 121.6 . . ? C1 C6 H6 121.6 . . ? O1 C1 C2 114.40(11) . . ? O1 C1 C6 124.65(12) . . ? C2 C1 C6 120.95(12) . . ? C5' C4' C3' 103.30(10) . . ? C5' C4' H4'1 111.1 . . ? C3' C4' H4'1 111.1 . . ? C5' C4' H4'2 111.1 . . ? C3' C4' H4'2 111.1 . . ? H4'1 C4' H4'2 109.1 . . ? C4' C5' C6' 102.55(10) . . ? C4' C5' H5'1 111.3 . . ? C6' C5' H5'1 111.3 . . ? C4' C5' H5'2 111.3 . . ? C6' C5' H5'2 111.3 . . ? H5'1 C5' H5'2 109.2 . . ? C7' C6' C5' 118.59(11) . . ? C7' C6' C2' 113.18(10) . . ? C5' C6' C2' 104.25(10) . . ? C7' C6' H6' 106.7 . . ? C5' C6' H6' 106.7 . . ? C2' C6' H6' 106.7 . . ? C8' C7' C9' 121.85(13) . . ? C8' C7' C6' 121.66(12) . . ? C9' C7' C6' 116.49(11) . . ? O9' C9' C7' 110.92(11) . . ? O9' C9' H9'1 109.5 . . ? C7' C9' H9'1 109.5 . . ? O9' C9' H9'2 109.5 . . ? C7' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 108.0 . . ? C7' C8' H8'1 120.0 . . ? C7' C8' H8'2 120.0 . . ? H8'1 C8' H8'2 120.0 . . ? 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 C11' O11' C10' O10' -2.8(2) . . . . ? C11' O11' C10' C3' 176.72(11) . . . . ? O10' C10' C3' C4' 176.88(13) . . . . ? O11' C10' C3' C4' -2.66(16) . . . . ? O10' C10' C3' C2' 52.82(17) . . . . ? O11' C10' C3' C2' -126.73(12) . . . . ? C1 O1 C2' C1' 7.58(12) . . . . ? C1 O1 C2' C3' 133.37(10) . . . . ? C1 O1 C2' C6' -110.87(11) . . . . ? C10' C3' C2' O1 -101.18(12) . . . . ? C4' C3' C2' O1 128.46(11) . . . . ? C10' C3' C2' C1' 17.87(15) . . . . ? C4' C3' C2' C1' -112.49(12) . . . . ? C10' C3' C2' C6' 139.20(11) . . . . ? C4' C3' C2' C6' 8.84(13) . . . . ? O1 C2' C1' O1' 174.83(11) . . . . ? C3' C2' C1' O1' 53.24(16) . . . . ? C6' C2' C1' O1' -65.63(15) . . . . ? O1 C2' C1' C2 -7.73(12) . . . . ? C3' C2' C1' C2 -129.32(12) . . . . ? C6' C2' C1' C2 111.80(11) . . . . ? O1' C1' C2 C1 -177.73(13) . . . . ? C2' C1' C2 C1 4.99(13) . . . . ? O1' C1' C2 C3 4.6(2) . . . . ? C2' C1' C2 C3 -172.66(13) . . . . ? C1 C2 C3 C4 -0.40(18) . . . . ? C1' C2 C3 C4 176.94(13) . . . . ? C2 C3 C4 O4 -177.17(11) . . . . ? C2 C3 C4 C5 2.16(19) . . . . ? O4 C4 C5 C6 177.79(12) . . . . ? C3 C4 C5 C6 -1.5(2) . . . . ? C4 C5 C6 C1 -0.98(19) . . . . ? C2' O1 C1 C2 -4.92(14) . . . . ? C2' O1 C1 C6 174.91(12) . . . . ? C3 C2 C1 O1 177.70(11) . . . . ? C1' C2 C1 O1 -0.23(14) . . . . ? C3 C2 C1 C6 -2.14(19) . . . . ? C1' C2 C1 C6 179.93(11) . . . . ? C5 C6 C1 O1 -177.07(11) . . . . ? C5 C6 C1 C2 2.75(18) . . . . ? C10' C3' C4' C5' -160.12(11) . . . . ? C2' C3' C4' C5' -32.60(13) . . . . ? C3' C4' C5' C6' 43.82(12) . . . . ? C4' C5' C6' C7' -165.01(11) . . . . ? C4' C5' C6' C2' -38.07(12) . . . . ? O1 C2' C6' C7' 29.50(15) . . . . ? C1' C2' C6' C7' -86.18(13) . . . . ? C3' C2' C6' C7' 148.17(11) . . . . ? O1 C2' C6' C5' -100.73(11) . . . . ? C1' C2' C6' C5' 143.59(11) . . . . ? C3' C2' C6' C5' 17.93(12) . . . . ? C5' C6' C7' C8' -162.61(13) . . . . ? C2' C6' C7' C8' 74.82(16) . . . . ? C5' C6' C7' C9' 17.74(17) . . . . ? C2' C6' C7' C9' -104.82(13) . . . . ? C8' C7' C9' O9' -10.27(19) . . . . ? C6' C7' C9' O9' 169.37(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O9' 0.84 1.83 2.6485(13) 162.8 2_466 O9' H9' O1' 0.84 1.92 2.7417(12) 166.1 3_556 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 69.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.244 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.038