# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/186 data_COMPOUND6 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H20 O5' _chemical_formula_weight 316.34 _chemical_melting_point ? _chemical_compound_source ? 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x, -y+1/2, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z-1/2' '-x, y-1/2, -z' 'x-1/2, y, -z-1/2' _cell_length_a 21.055(13) _cell_length_b 14.453(8) _cell_length_c 5.099(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1551.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 4.1 _cell_measurement_theta_max 10.2 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method ? _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'SIEMENS R3m/V ' _diffrn_measurement_method THETA-2THETA _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1423 _diffrn_reflns_av_R_equivalents 0.0044 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1422 _reflns_number_observed 785 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER P4 SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL PC VERS. 5.03 (Sheldrick, 1994)' _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+0.0000P] 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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(25) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1422 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_obs 0.0586 _refine_ls_wR_factor_all 0.1570 _refine_ls_wR_factor_obs 0.1362 _refine_ls_goodness_of_fit_all 0.968 _refine_ls_goodness_of_fit_obs 1.166 _refine_ls_restrained_S_all 0.968 _refine_ls_restrained_S_obs 1.166 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O2 O 0.38590(10) 0.34711(15) 0.1694(4) 0.0540(7) Uani 1 d . . O3 O 0.29555(10) 0.3490(2) 0.5034(4) 0.0517(6) Uani 1 d . . O5 O 0.4647(2) 0.2500 -0.3879(8) 0.0551(12) Uani 0.75 d SP . H5A H 0.4375(2) 0.2500 -0.5532(8) 0.080 Uiso 0.75 d SPR . O5' O 0.1911(7) 0.2500 0.4348(31) 0.068(4) Uiso 0.25 d SP . C2 C 0.4254(2) 0.2500 -0.1664(8) 0.0461(11) Uani 1 d S . H2 H 0.3812(2) 0.2500 -0.2125(8) 0.050 Uiso 1 d SR . C3 C 0.43653(14) 0.3381(2) -0.0135(6) 0.0465(8) Uani 1 d . . H3A H 0.43692(14) 0.3902(2) -0.1303(6) 0.055 Uiso 1 d R . H3B H 0.47632(14) 0.3348(2) 0.0779(6) 0.055 Uiso 1 d R . C4 C 0.38291(14) 0.4251(2) 0.3199(6) 0.0417(7) Uani 1 d . . C5 C 0.42335(15) 0.4990(2) 0.3060(7) 0.0489(8) Uani 1 d . . H5 H 0.45681(15) 0.4992(2) 0.1781(7) 0.054 Uiso 1 d R . C6 C 0.41662(15) 0.5735(2) 0.4745(7) 0.0549(9) Uani 1 d . . H6 H 0.44525(15) 0.6251(2) 0.4635(7) 0.066 Uiso 1 d R . C7 C 0.3691(2) 0.5731(2) 0.6566(7) 0.0571(9) Uani 1 d . . H7 H 0.3647(2) 0.6245(2) 0.7747(7) 0.067 Uiso 1 d R . C8 C 0.32668(15) 0.4994(2) 0.6735(7) 0.0508(9) Uani 1 d . . H8 H 0.29299(15) 0.5003(2) 0.8003(7) 0.056 Uiso 1 d R . C9 C 0.33347(14) 0.4250(2) 0.5057(6) 0.0418(7) Uani 1 d . . C10 C 0.24988(15) 0.3389(2) 0.7092(7) 0.0527(9) Uani 1 d . . H10A H 0.27126(15) 0.3371(2) 0.8754(7) 0.060 Uiso 1 d R . H10B H 0.22086(15) 0.3902(2) 0.7063(7) 0.060 Uiso 1 d R . C11 C 0.2137(2) 0.2500 0.6674(11) 0.0549(13) Uani 1 d S . H11 H 0.1620(2) 0.2500 0.7517(11) 0.046 Uiso 1 d SR . 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 O2 0.0655(14) 0.0525(13) 0.0441(13) -0.0075(12) 0.0203(12) -0.0091(12) O3 0.0585(12) 0.0507(13) 0.0458(12) -0.0041(12) 0.0136(12) -0.0053(11) O5 0.074(3) 0.063(3) 0.028(2) 0.000 0.011(2) 0.000 C2 0.051(2) 0.058(3) 0.029(2) 0.000 0.006(2) 0.000 C3 0.053(2) 0.053(2) 0.034(2) 0.003(2) 0.007(2) -0.0034(15) C4 0.053(2) 0.042(2) 0.0308(15) 0.0007(15) -0.0031(15) 0.0013(14) C5 0.055(2) 0.054(2) 0.038(2) -0.001(2) 0.003(2) -0.004(2) C6 0.060(2) 0.049(2) 0.055(2) -0.002(2) -0.002(2) -0.007(2) C7 0.067(2) 0.053(2) 0.052(2) -0.012(2) -0.008(2) 0.004(2) C8 0.053(2) 0.056(2) 0.044(2) -0.009(2) 0.000(2) 0.008(2) C9 0.048(2) 0.042(2) 0.035(2) -0.001(2) -0.003(2) 0.0018(14) C10 0.050(2) 0.060(2) 0.049(2) -0.002(2) 0.014(2) 0.003(2) C11 0.046(3) 0.055(3) 0.064(3) 0.000 0.007(3) 0.000 _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 O2 C4 1.365(3) . ? O2 C3 1.423(3) . ? O3 C9 1.358(4) . ? O3 C10 1.431(4) . ? O5 C2 1.400(6) . ? O5' C11 1.28(2) . ? C2 C3 1.512(4) . ? C2 C3 1.512(4) 3 ? C4 C5 1.367(4) . ? C4 C9 1.408(4) . ? C5 C6 1.386(5) . ? C6 C7 1.366(5) . ? C7 C8 1.393(5) . ? C8 C9 1.381(4) . ? C10 C11 1.509(4) . ? C11 C10 1.509(4) 3 ? 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 O2 C3 118.6(2) . . ? C9 O3 C10 118.1(3) . . ? O5 C2 C3 108.9(2) . . ? O5 C2 C3 108.9(2) . 3 ? C3 C2 C3 114.8(4) . 3 ? O2 C3 C2 107.4(3) . . ? O2 C4 C5 125.9(3) . . ? O2 C4 C9 114.3(3) . . ? C5 C4 C9 119.8(3) . . ? C4 C5 C6 120.7(3) . . ? C7 C6 C5 119.6(3) . . ? C6 C7 C8 121.0(3) . . ? C9 C8 C7 119.4(3) . . ? O3 C9 C8 125.0(3) . . ? O3 C9 C4 115.5(3) . . ? C8 C9 C4 119.5(3) . . ? O3 C10 C11 108.8(3) . . ? O5' C11 C10 108.6(4) . . ? O5' C11 C10 108.6(4) . 3 ? C10 C11 C10 116.8(4) . 3 ? 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 O2 C3 C2 -175.6(3) . . . . ? O5 C2 C3 O2 165.8(3) . . . . ? C3 C2 C3 O2 -71.8(4) 3 . . . ? C3 O2 C4 C5 2.6(4) . . . . ? C3 O2 C4 C9 -176.3(3) . . . . ? O2 C4 C5 C6 -178.2(3) . . . . ? C9 C4 C5 C6 0.6(5) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C8 -0.8(5) . . . . ? C6 C7 C8 C9 0.9(5) . . . . ? C10 O3 C9 C8 -8.1(4) . . . . ? C10 O3 C9 C4 171.8(3) . . . . ? C7 C8 C9 O3 179.7(3) . . . . ? C7 C8 C9 C4 -0.2(5) . . . . ? O2 C4 C9 O3 -1.5(4) . . . . ? C5 C4 C9 O3 179.6(3) . . . . ? O2 C4 C9 C8 178.4(3) . . . . ? C5 C4 C9 C8 -0.5(4) . . . . ? C9 O3 C10 C11 -179.7(3) . . . . ? O3 C10 C11 O5' -53.5(7) . . . . ? O3 C10 C11 C10 69.6(5) . . . 3 ? _refine_diff_density_max 0.279 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.048 #===END data_COMPOUND7 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H22 O5' _chemical_formula_weight 330.37 _chemical_melting_point ? _chemical_compound_source ? 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.621(10) _cell_length_b 9.499(11) _cell_length_c 10.262(7) _cell_angle_alpha 90.00 _cell_angle_beta 115.39(6) _cell_angle_gamma 90.00 _cell_volume 847.3(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 4.9 _cell_measurement_theta_max 10.2 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method ? _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'BRUKER P4' _diffrn_measurement_method 'THETA 2THETA SCANS' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1270 _diffrn_reflns_av_R_equivalents 0.1552 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 22.54 _reflns_number_total 1190 _reflns_number_observed 821 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL PC VREC. 5.03 (Sheldrick, 1994)' _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0265(163) _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 2.58(530) _refine_ls_number_reflns 1190 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_obs 0.0843 _refine_ls_wR_factor_all 0.2268 _refine_ls_wR_factor_obs 0.2071 _refine_ls_goodness_of_fit_all 1.007 _refine_ls_goodness_of_fit_obs 1.156 _refine_ls_restrained_S_all 1.007 _refine_ls_restrained_S_obs 1.156 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.0707(8) -0.0655(11) 0.2210(8) 0.067(2) Uani 1 d . . C1 C -0.0158(14) -0.1776(15) 0.1295(13) 0.076(4) Uani 1 d . . H1A H -0.0523(14) -0.2403(15) 0.1815(13) 0.091 Uiso 1 d R . H1B H -0.1020(14) -0.1397(15) 0.0479(13) 0.091 Uiso 1 d R . C2 C 0.0891(16) -0.2529(17) 0.0764(15) 0.095(5) Uani 1 d . . H2A H 0.1839(16) -0.2735(17) 0.1588(15) 0.114 Uiso 1 d R . H2B H 0.0399(16) -0.3396(17) 0.0318(15) 0.114 Uiso 1 d R . C3 C 0.1268(13) -0.1679(14) -0.0300(12) 0.068(3) Uani 1 d . . H3A H 0.0335(13) -0.1307(14) -0.1043(12) 0.081 Uiso 1 d R . H3B H 0.1768(13) -0.2275(14) -0.0727(12) 0.081 Uiso 1 d R . O2 O 0.2231(8) -0.0573(11) 0.0444(7) 0.061(2) Uani 1 d . . C4 C 0.2839(11) 0.0266(15) -0.0276(10) 0.054(3) Uani 1 d . . C5 C 0.2622(13) 0.0027(16) -0.1690(10) 0.064(3) Uani 1 d . . H5 H 0.2007(13) -0.0755(16) -0.2226(10) 0.077 Uiso 1 d R . C6 C 0.3297(14) 0.0883(17) -0.2307(11) 0.067(3) Uani 1 d . . H6 H 0.3138(14) 0.0710(17) -0.3283(11) 0.081 Uiso 1 d R . C7 C 0.4208(13) 0.1978(17) -0.1566(11) 0.071(4) Uani 1 d . . H7 H 0.4681(13) 0.2567(17) -0.2023(11) 0.085 Uiso 1 d R . C8 C 0.4399(11) 0.2251(17) -0.0146(11) 0.062(3) Uani 1 d . . H8 H 0.5060(11) 0.3009(17) 0.0392(11) 0.074 Uiso 1 d R . C9 C 0.3682(10) 0.1389(14) 0.0473(10) 0.048(2) Uani 1 d . . O3 O 0.3795(7) 0.1562 0.1831(6) 0.057(2) Uani 1 d . . C10 C 0.4419(11) 0.2827(12) 0.2541(9) 0.047(2) Uani 1 d . . H10A H 0.5444(11) 0.2932(12) 0.2611(9) 0.057 Uiso 1 d R . H10B H 0.3794(11) 0.3605(12) 0.2008(9) 0.057 Uiso 1 d R . C11 C 0.4508(10) 0.2798(14) 0.4104(9) 0.047(2) Uani 1 d . . H11 H 0.4973(10) 0.1924(14) 0.4551(9) 0.056 Uiso 1 d R . C19 C 0.5456(12) 0.3978(14) 0.4928(10) 0.058(3) Uani 1 d . . H19A H 0.4977(12) 0.4858(14) 0.4518(10) 0.069 Uiso 1 d R . H19B H 0.6448(12) 0.3926(14) 0.4919(10) 0.069 Uiso 1 d R . O5 O 0.5626(9) 0.3920(12) 0.6353(7) 0.077(3) Uani 1 d . . H5A H 0.6159(9) 0.4938(12) 0.6739(7) 0.092 Uiso 1 d R . C12 C 0.2947(10) 0.2786(15) 0.4125(10) 0.054(3) Uani 1 d . . H12A H 0.2335(10) 0.3554(15) 0.3556(10) 0.064 Uiso 1 d R . H12B H 0.3088(10) 0.2890(15) 0.5104(10) 0.064 Uiso 1 d R . O4 O 0.2179(7) 0.1517(11) 0.3570(7) 0.058(2) Uani 1 d . . C13 C 0.0758(10) 0.1287(16) 0.3561(10) 0.055(3) Uani 1 d . . C14 C 0.0176(13) 0.2177(16) 0.4327(12) 0.066(3) Uani 1 d . . H14 H 0.0716(13) 0.2997(16) 0.4849(12) 0.079 Uiso 1 d R . C15 C -0.1287(12) 0.1782(18) 0.4250(13) 0.075(4) Uani 1 d . . H15 H -0.1724(12) 0.2317(18) 0.4777(13) 0.090 Uiso 1 d R . C16 C -0.2069(12) 0.0708(17) 0.3506(14) 0.070(3) Uani 1 d . . H16 H -0.3082(12) 0.0518(17) 0.3434(14) 0.084 Uiso 1 d R . C17 C -0.1463(12) -0.0137(16) 0.2763(12) 0.071(3) Uani 1 d . . H17 H -0.2022(12) -0.0945(16) 0.2230(12) 0.085 Uiso 1 d R . C18 C -0.0027(11) 0.0167(14) 0.2846(10) 0.050(3) Uani 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 O1 0.069(4) 0.065(5) 0.086(5) -0.016(4) 0.050(4) -0.019(4) C1 0.065(7) 0.073(9) 0.088(8) -0.010(7) 0.032(6) -0.035(7) C2 0.107(10) 0.071(9) 0.130(11) -0.043(9) 0.074(9) -0.052(8) C3 0.082(8) 0.062(7) 0.063(7) -0.016(6) 0.034(6) -0.014(7) O2 0.081(5) 0.058(5) 0.052(4) -0.012(4) 0.037(4) -0.019(4) C4 0.049(5) 0.068(8) 0.047(6) 0.002(6) 0.024(5) 0.007(6) C5 0.080(7) 0.078(8) 0.048(6) -0.002(6) 0.040(5) 0.021(7) C6 0.080(8) 0.085(8) 0.046(6) -0.002(7) 0.036(6) 0.023(7) C7 0.078(8) 0.105(11) 0.057(6) 0.025(7) 0.053(6) 0.027(8) C8 0.052(6) 0.083(8) 0.062(6) 0.012(6) 0.035(5) 0.006(6) C9 0.051(5) 0.054(6) 0.040(5) 0.008(5) 0.021(4) 0.007(5) O3 0.075(4) 0.074(5) 0.038(3) -0.016(4) 0.039(3) -0.029(4) C10 0.053(5) 0.051(6) 0.046(5) -0.007(5) 0.028(4) -0.011(5) C11 0.046(5) 0.065(7) 0.036(5) 0.008(5) 0.025(4) 0.005(5) C19 0.064(7) 0.075(8) 0.046(5) -0.015(6) 0.035(5) -0.017(6) O5 0.096(6) 0.103(7) 0.047(4) -0.019(4) 0.045(4) -0.042(5) C12 0.049(6) 0.074(8) 0.045(5) -0.009(6) 0.027(4) -0.010(6) O4 0.045(4) 0.080(5) 0.065(4) -0.022(4) 0.039(3) -0.022(4) C13 0.036(5) 0.085(9) 0.047(5) 0.002(6) 0.022(4) -0.001(6) C14 0.065(7) 0.073(8) 0.068(7) 0.002(6) 0.037(6) 0.002(6) C15 0.057(7) 0.104(11) 0.091(8) 0.020(9) 0.058(7) 0.022(8) C16 0.044(6) 0.070(8) 0.104(9) 0.004(8) 0.038(7) -0.004(7) C17 0.053(6) 0.086(9) 0.083(7) 0.010(7) 0.038(6) -0.002(7) C18 0.046(5) 0.057(7) 0.052(5) 0.002(6) 0.026(4) -0.015(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 O1 C18 1.389(12) . ? O1 C1 1.427(13) . ? C1 C2 1.52(2) . ? C2 C3 1.52(2) . ? C3 O2 1.392(12) . ? O2 C4 1.377(12) . ? C4 C9 1.360(14) . ? C4 C5 1.394(14) . ? C5 C6 1.35(2) . ? C6 C7 1.36(2) . ? C7 C8 1.412(15) . ? C8 C9 1.388(14) . ? C9 O3 1.360(11) . ? O3 C10 1.401(11) . ? C10 C11 1.569(11) . ? C11 C19 1.463(14) . ? C11 C12 1.511(12) . ? C19 O5 1.401(11) . ? C12 O4 1.401(12) . ? O4 C13 1.380(11) . ? C13 C18 1.329(14) . ? C13 C14 1.42(2) . ? C14 C15 1.42(2) . ? C15 C16 1.30(2) . ? C16 C17 1.40(2) . ? C17 C18 1.378(13) . ? 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 C18 O1 C1 117.2(8) . . ? O1 C1 C2 107.3(9) . . ? C1 C2 C3 114.0(12) . . ? O2 C3 C2 108.3(9) . . ? C4 O2 C3 118.6(8) . . ? C9 C4 O2 116.0(8) . . ? C9 C4 C5 120.2(10) . . ? O2 C4 C5 123.8(10) . . ? C6 C5 C4 120.1(11) . . ? C5 C6 C7 121.3(10) . . ? C6 C7 C8 119.0(11) . . ? C9 C8 C7 119.5(12) . . ? C4 C9 O3 116.1(8) . . ? C4 C9 C8 119.8(9) . . ? O3 C9 C8 124.1(10) . . ? C9 O3 C10 117.7(7) . . ? O3 C10 C11 109.9(7) . . ? C19 C11 C12 112.0(8) . . ? C19 C11 C10 108.9(8) . . ? C12 C11 C10 113.3(7) . . ? O5 C19 C11 109.8(8) . . ? O4 C12 C11 110.8(8) . . ? C13 O4 C12 119.2(8) . . ? C18 C13 O4 117.2(9) . . ? C18 C13 C14 121.0(9) . . ? O4 C13 C14 121.7(10) . . ? C13 C14 C15 115.2(12) . . ? C16 C15 C14 123.2(11) . . ? C15 C16 C17 120.0(10) . . ? C18 C17 C16 119.2(12) . . ? C13 C18 C17 121.3(11) . . ? C13 C18 O1 115.2(8) . . ? C17 C18 O1 123.5(10) . . ? 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 C18 O1 C1 C2 -178.8(10) . . . . ? O1 C1 C2 C3 -70.1(13) . . . . ? C1 C2 C3 O2 70.3(13) . . . . ? C2 C3 O2 C4 174.1(10) . . . . ? C3 O2 C4 C9 175.5(8) . . . . ? C3 O2 C4 C5 -3.9(14) . . . . ? C9 C4 C5 C6 2.4(14) . . . . ? O2 C4 C5 C6 -178.2(10) . . . . ? C4 C5 C6 C7 0.7(16) . . . . ? C5 C6 C7 C8 -2.4(16) . . . . ? C6 C7 C8 C9 1.1(15) . . . . ? O2 C4 C9 O3 -1.3(12) . . . . ? C5 C4 C9 O3 178.1(9) . . . . ? O2 C4 C9 C8 176.9(9) . . . . ? C5 C4 C9 C8 -3.7(13) . . . . ? C7 C8 C9 C4 1.9(15) . . . . ? C7 C8 C9 O3 179.9(9) . . . . ? C4 C9 O3 C10 -169.2(8) . . . . ? C8 C9 O3 C10 12.7(13) . . . . ? C9 O3 C10 C11 -177.9(8) . . . . ? O3 C10 C11 C19 167.9(8) . . . . ? O3 C10 C11 C12 -66.7(11) . . . . ? C12 C11 C19 O5 57.4(11) . . . . ? C10 C11 C19 O5 -176.4(8) . . . . ? C19 C11 C12 O4 -168.8(8) . . . . ? C10 C11 C12 O4 67.5(11) . . . . ? C11 C12 O4 C13 177.2(8) . . . . ? C12 O4 C13 C18 170.7(8) . . . . ? C12 O4 C13 C14 -11.6(14) . . . . ? C18 C13 C14 C15 -0.6(16) . . . . ? O4 C13 C14 C15 -178.2(10) . . . . ? C13 C14 C15 C16 -1.7(18) . . . . ? C14 C15 C16 C17 1.5(19) . . . . ? C15 C16 C17 C18 1.0(18) . . . . ? O4 C13 C18 C17 -179.2(9) . . . . ? C14 C13 C18 C17 3.1(15) . . . . ? O4 C13 C18 O1 1.1(12) . . . . ? C14 C13 C18 O1 -176.6(9) . . . . ? C16 C17 C18 C13 -3.3(16) . . . . ? C16 C17 C18 O1 176.4(11) . . . . ? C1 O1 C18 C13 -173.1(9) . . . . ? C1 O1 C18 C17 7.3(14) . . . . ? _refine_diff_density_max 0.289 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.080 #===END data_COMPOUND8 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H22 O5' _chemical_formula_weight 330.37 _chemical_melting_point ? _chemical_compound_source ? 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z' 'x, -y, z+1/2' '-x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' _cell_length_a 17.060(7) _cell_length_b 17.922(5) _cell_length_c 5.552(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1697.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 17.5 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method ? _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'BRUKER P4' _diffrn_measurement_method 'THETA 2-THETA' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1648 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.07 _reflns_number_total 870 _reflns_number_observed 501 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL PC VERS.5.03 (Sheldrick, 1994)' _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(13) _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 -2.83(354) _refine_ls_number_reflns 870 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_obs 0.0494 _refine_ls_wR_factor_all 0.1252 _refine_ls_wR_factor_obs 0.1097 _refine_ls_goodness_of_fit_all 0.916 _refine_ls_goodness_of_fit_obs 1.116 _refine_ls_restrained_S_all 0.916 _refine_ls_restrained_S_obs 1.116 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C2 C 0.0000 0.4005(3) 0.6975(14) 0.058(2) Uani 1 d S . H2A H 0.0000 0.4376(3) 0.8708(14) 0.065 Uiso 1 d SR . H2B H 0.0000 0.3390(3) 0.7518(14) 0.065 Uiso 1 d SR . C3 C 0.0746(2) 0.4135(2) 0.5556(13) 0.0541(11) Uani 1 d . . H3A H 0.1184(2) 0.4142(2) 0.6639(13) 0.065 Uiso 1 d R . H3B H 0.0716(2) 0.4602(2) 0.4715(13) 0.065 Uiso 1 d R . O2 O 0.0836(2) 0.35442(15) 0.3891 0.0627(10) Uani 1 d . . C4 C 0.1442(2) 0.3578(2) 0.2286(12) 0.0522(12) Uani 1 d . . C5 C 0.2028(3) 0.4096(3) 0.2322(13) 0.0625(13) Uani 1 d . . H5 H 0.2027(3) 0.4482(3) 0.3522(13) 0.073 Uiso 1 d R . C6 C 0.2633(3) 0.4065(3) 0.0616(14) 0.0739(15) Uani 1 d . . H6 H 0.3047(3) 0.4428(3) 0.0651(14) 0.087 Uiso 1 d R . C7 C 0.2632(3) 0.3508(3) -0.1125(14) 0.074(2) Uani 1 d . . H7 H 0.3046(3) 0.3484(3) -0.2293(14) 0.091 Uiso 1 d R . C8 C 0.2032(3) 0.2986(3) -0.1159(13) 0.0634(13) Uani 1 d . . H8 H 0.2030(3) 0.2600(3) -0.2355(13) 0.077 Uiso 1 d R . C9 C 0.1444(3) 0.3018(3) 0.0502(12) 0.0565(12) Uani 1 d . . O3 O 0.0814(2) 0.2545(2) 0.0609(10) 0.0662(10) Uani 1 d . . C10 C 0.0737(3) 0.1974(3) -0.1182(13) 0.0658(13) Uani 1 d . . H10A H 0.0687(3) 0.2197(3) -0.2747(13) 0.079 Uiso 1 d R . H10B H 0.1189(3) 0.1655(3) -0.1155(13) 0.079 Uiso 1 d R . C11 C 0.0000 0.1532(5) -0.0586(17) 0.067(2) Uani 1 d S . C19 C 0.0000 0.0815(4) -0.2087(23) 0.106(4) Uani 1 d S . H19A H 0.0000 0.0980(4) -0.3668(23) 0.120 Uiso 1 d SR . H19B H 0.0582 0.0684(4) -0.1886(23) 0.120 Uiso 0.50 d PR . O5 O 0.0000 0.1334(4) 0.1934(15) 0.110(2) Uani 1 d S . H5A H 0.0000 0.1924(4) 0.3136(15) 0.150 Uiso 1 d SR . 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 C2 0.057(4) 0.051(4) 0.065(5) -0.009(4) 0.000 0.000 C3 0.053(3) 0.045(2) 0.065(3) -0.009(3) -0.005(3) 0.002(2) O2 0.058(2) 0.060(2) 0.070(2) -0.023(2) 0.008(2) -0.004(2) C4 0.036(2) 0.060(3) 0.060(3) 0.000(3) 0.000(3) 0.002(2) C5 0.054(3) 0.055(3) 0.078(3) 0.002(3) -0.003(3) 0.008(2) C6 0.054(3) 0.078(3) 0.090(4) 0.025(4) 0.000(4) 0.003(3) C7 0.060(3) 0.093(4) 0.069(4) 0.022(4) 0.003(3) 0.019(3) C8 0.050(3) 0.073(3) 0.067(3) 0.003(3) 0.001(3) 0.012(3) C9 0.047(3) 0.069(3) 0.054(3) -0.005(3) -0.001(3) 0.014(2) O3 0.052(2) 0.073(2) 0.074(2) -0.022(2) 0.003(2) 0.001(2) C10 0.076(3) 0.070(3) 0.052(3) -0.019(3) -0.012(3) 0.019(3) C11 0.081(5) 0.070(5) 0.052(5) -0.006(4) 0.000 0.000 C19 0.133(8) 0.057(4) 0.127(10) -0.050(6) 0.000 0.000 O5 0.159(6) 0.105(5) 0.066(5) 0.024(4) 0.000 0.000 _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 C2 C3 1.514(6) 2 ? C2 C3 1.514(6) . ? C3 O2 1.414(5) . ? O2 C4 1.366(5) . ? C4 C5 1.364(6) . ? C4 C9 1.411(7) . ? C5 C6 1.402(7) . ? C6 C7 1.389(8) . ? C7 C8 1.387(6) . ? C8 C9 1.363(7) . ? C9 O3 1.370(5) . ? O3 C10 1.433(6) . ? C10 C11 1.523(6) . ? C11 O5 1.444(9) . ? C11 C10 1.523(6) 2 ? C11 C19 1.531(10) . ? 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 C3 C2 C3 114.3(6) 2 . ? O2 C3 C2 108.5(4) . . ? C4 O2 C3 118.4(3) . . ? C5 C4 O2 125.1(5) . . ? C5 C4 C9 119.5(5) . . ? O2 C4 C9 115.4(4) . . ? C4 C5 C6 120.2(5) . . ? C7 C6 C5 119.8(5) . . ? C8 C7 C6 119.6(6) . . ? C9 C8 C7 120.4(5) . . ? C8 C9 O3 125.5(5) . . ? C8 C9 C4 120.4(5) . . ? O3 C9 C4 114.1(4) . . ? C9 O3 C10 118.9(4) . . ? O3 C10 C11 107.2(5) . . ? O5 C11 C10 109.8(5) . 2 ? O5 C11 C10 109.8(5) . . ? C10 C11 C10 111.4(6) 2 . ? O5 C11 C19 108.8(8) . . ? C10 C11 C19 108.6(5) 2 . ? C10 C11 C19 108.6(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 C3 C2 C3 O2 -72.3(6) 2 . . . ? C2 C3 O2 C4 175.0(4) . . . . ? C3 O2 C4 C5 7.9(6) . . . . ? C3 O2 C4 C9 -172.9(4) . . . . ? O2 C4 C5 C6 178.3(5) . . . . ? C9 C4 C5 C6 -0.9(7) . . . . ? C4 C5 C6 C7 0.5(7) . . . . ? C5 C6 C7 C8 -0.1(8) . . . . ? C6 C7 C8 C9 0.0(8) . . . . ? C7 C8 C9 O3 178.4(4) . . . . ? C7 C8 C9 C4 -0.4(7) . . . . ? C5 C4 C9 C8 0.9(7) . . . . ? O2 C4 C9 C8 -178.4(4) . . . . ? C5 C4 C9 O3 -178.1(4) . . . . ? O2 C4 C9 O3 2.6(6) . . . . ? C8 C9 O3 C10 -1.6(7) . . . . ? C4 C9 O3 C10 177.3(4) . . . . ? C9 O3 C10 C11 179.0(4) . . . . ? O3 C10 C11 O5 -48.3(6) . . . . ? O3 C10 C11 C10 73.4(7) . . . 2 ? O3 C10 C11 C19 -167.1(6) . . . . ? _refine_diff_density_max 0.185 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.034 #===END data_COMPOUND9 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H20 O6' _chemical_formula_weight 332.34 _chemical_melting_point ? _chemical_compound_source ? 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.139(8) _cell_length_b 5.0640(10) _cell_length_c 20.155(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.30(2) _cell_angle_gamma 90.00 _cell_volume 3211.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 13.9 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method ? _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'BRUKER P4' _diffrn_measurement_method 'THETA 2THETA' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2893 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2824 _reflns_number_observed 1576 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL PC VERS. 5.03 (Sheldrick, 1994)' _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2824 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_obs 0.0492 _refine_ls_wR_factor_all 0.1168 _refine_ls_wR_factor_obs 0.1021 _refine_ls_goodness_of_fit_all 0.981 _refine_ls_goodness_of_fit_obs 1.185 _refine_ls_restrained_S_all 0.981 _refine_ls_restrained_S_obs 1.185 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.13050(6) -0.1562(4) 0.15499(9) 0.0579(6) Uani 1 d . . C1 C 0.09980(8) -0.3453(5) 0.15879(14) 0.0470(7) Uani 1 d . . H1A H 0.11196(8) -0.4654(5) 0.19665(14) 0.056 Uiso 1 d R . H1B H 0.07581(8) -0.2578(5) 0.16596(14) 0.056 Uiso 1 d R . C2 C 0.08606(9) -0.4943(5) 0.09028(14) 0.0463(7) Uani 1 d . . H2 H 0.11186(9) -0.5409(5) 0.08105(14) 0.056 Uiso 1 d R . O6 O 0.06112(6) -0.7135(4) 0.09804(11) 0.0632(6) Uani 1 d . . H6A H 0.08813(6) -0.8868(4) 0.11138(11) 0.095 Uiso 1 d R . C3 C 0.05986(8) -0.3385(5) 0.02741(14) 0.0455(7) Uani 1 d . . H3A H 0.03721(8) -0.2478(5) 0.03806(14) 0.055 Uiso 1 d R . H3B H 0.04819(8) -0.4551(5) -0.01145(14) 0.055 Uiso 1 d R . O2 O 0.08755(6) -0.1536(4) 0.01117(9) 0.0529(5) Uani 1 d . . C4 C 0.07254(8) -0.0007(5) -0.04774(13) 0.0410(6) Uani 1 d . . C5 C 0.03264(8) -0.0190(6) -0.09570(14) 0.0514(8) Uani 1 d . . H5 H 0.01282(8) -0.1485(6) -0.08999(14) 0.062 Uiso 1 d R . C6 C 0.02126(10) 0.1504(7) -0.1528(2) 0.0624(9) Uani 1 d . . H6 H -0.00659(10) 0.1375(7) -0.1864(2) 0.075 Uiso 1 d R . C7 C 0.04896(10) 0.3345(7) -0.16162(15) 0.0602(8) Uani 1 d . . H7 H 0.04064(10) 0.4505(7) -0.20127(15) 0.072 Uiso 1 d R . C8 C 0.08949(9) 0.3549(6) -0.11307(14) 0.0504(7) Uani 1 d . . H8 H 0.10901(9) 0.4861(6) -0.11886(14) 0.060 Uiso 1 d R . C9 C 0.10136(8) 0.1864(5) -0.05683(12) 0.0395(6) Uani 1 d . . O3 O 0.14028(5) 0.1867(4) -0.00616(8) 0.0475(5) Uani 1 d . . C10 C 0.16999(8) 0.3870(6) -0.00791(13) 0.0479(7) Uani 1 d . . H10A H 0.17489(8) 0.3855(6) -0.05238(13) 0.058 Uiso 1 d R . H10B H 0.15931(8) 0.5569(6) -0.00038(13) 0.058 Uiso 1 d R . C11 C 0.21105(8) 0.3284(6) 0.04957(14) 0.0475(7) Uani 1 d . . H11 H 0.23099(8) 0.4566(6) 0.04365(14) 0.057 Uiso 1 d R . O5 O 0.22442(6) 0.0651(4) 0.04159(10) 0.0650(6) Uani 1 d . . H5A H 0.20007(6) -0.0369(4) 0.05339(10) 0.078 Uiso 1 d R . C12 C 0.21073(8) 0.3737(6) 0.12370(13) 0.0495(7) Uani 1 d . . H12A H 0.19946(8) 0.5456(6) 0.12760(13) 0.059 Uiso 1 d R . H12B H 0.23909(8) 0.3603(6) 0.15559(13) 0.059 Uiso 1 d R . O4 O 0.18450(5) 0.1752(4) 0.13894(8) 0.0501(5) Uani 1 d . . C13 C 0.18085(8) 0.1689(5) 0.20460(13) 0.0405(6) Uani 1 d . . C14 C 0.20299(8) 0.3253(6) 0.25974(14) 0.0477(7) Uani 1 d . . H14 H 0.22330(8) 0.4510(6) 0.25393(14) 0.057 Uiso 1 d R . C15 C 0.19606(9) 0.3002(6) 0.32423(14) 0.0539(8) Uani 1 d . . H15 H 0.21184(9) 0.4077(6) 0.36291(14) 0.065 Uiso 1 d R . C16 C 0.16693(10) 0.1231(6) 0.33228(15) 0.0550(8) Uani 1 d . . H16 H 0.16225(10) 0.1065(6) 0.37676(15) 0.066 Uiso 1 d R . C17 C 0.14413(9) -0.0324(6) 0.27701(14) 0.0518(7) Uani 1 d . . H17 H 0.12338(9) -0.1548(6) 0.28283(14) 0.062 Uiso 1 d R . C18 C 0.15107(8) -0.0121(5) 0.21340(13) 0.0426(7) Uani 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 O1 0.0766(13) 0.0549(13) 0.0464(11) -0.0052(10) 0.0254(10) -0.0354(12) C1 0.050(2) 0.035(2) 0.062(2) -0.0021(14) 0.0270(14) -0.0049(14) C2 0.047(2) 0.035(2) 0.063(2) -0.0056(15) 0.0262(14) -0.0098(15) O6 0.0694(13) 0.0372(12) 0.0850(15) 0.0032(11) 0.0273(11) -0.0178(11) C3 0.0449(15) 0.038(2) 0.057(2) -0.0084(14) 0.0203(13) -0.0070(14) O2 0.0461(11) 0.0506(12) 0.0588(12) 0.0093(10) 0.0120(9) -0.0147(10) C4 0.043(2) 0.039(2) 0.042(2) -0.0014(14) 0.0146(13) 0.0033(14) C5 0.041(2) 0.058(2) 0.055(2) -0.013(2) 0.0147(14) -0.005(2) C6 0.052(2) 0.080(2) 0.049(2) -0.001(2) 0.0065(15) 0.010(2) C7 0.061(2) 0.071(2) 0.047(2) 0.006(2) 0.013(2) 0.010(2) C8 0.058(2) 0.052(2) 0.045(2) -0.0010(15) 0.0210(14) 0.002(2) C9 0.0416(15) 0.042(2) 0.0362(15) -0.0031(13) 0.0139(12) 0.0003(14) O3 0.0422(11) 0.0521(12) 0.0463(11) 0.0066(9) 0.0113(9) -0.0129(10) C10 0.050(2) 0.049(2) 0.049(2) 0.0037(14) 0.0223(14) -0.0106(15) C11 0.042(2) 0.049(2) 0.056(2) 0.003(2) 0.0216(13) -0.011(2) O5 0.0612(13) 0.0697(15) 0.0717(14) 0.0038(12) 0.0319(11) 0.0083(12) C12 0.046(2) 0.051(2) 0.054(2) 0.0015(14) 0.0197(14) -0.0153(15) O4 0.0570(12) 0.0563(12) 0.0394(11) -0.0045(9) 0.0188(9) -0.0258(10) C13 0.0404(14) 0.040(2) 0.0406(15) 0.0007(14) 0.0127(12) -0.0020(14) C14 0.043(2) 0.046(2) 0.053(2) -0.009(2) 0.0145(13) -0.0038(15) C15 0.059(2) 0.055(2) 0.047(2) -0.0130(15) 0.0142(15) 0.001(2) C16 0.072(2) 0.053(2) 0.044(2) -0.002(2) 0.024(2) 0.003(2) C17 0.068(2) 0.047(2) 0.047(2) 0.0009(15) 0.0275(15) -0.008(2) C18 0.051(2) 0.037(2) 0.039(2) -0.0006(13) 0.0136(13) -0.0041(14) _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 C18 1.371(3) . ? O1 C1 1.416(3) . ? C1 C2 1.513(3) . ? C2 O6 1.421(3) . ? C2 C3 1.514(4) . ? C3 O2 1.419(3) . ? O2 C4 1.373(3) . ? C4 C5 1.374(3) . ? C4 C9 1.398(3) . ? C5 C6 1.389(4) . ? C6 C7 1.359(4) . ? C7 C8 1.395(4) . ? C8 C9 1.374(4) . ? C9 O3 1.371(3) . ? O3 C10 1.422(3) . ? C10 C11 1.514(3) . ? C11 O5 1.430(3) . ? C11 C12 1.515(3) . ? C12 O4 1.424(3) . ? O4 C13 1.367(3) . ? C13 C14 1.374(3) . ? C13 C18 1.399(3) . ? C14 C15 1.395(4) . ? C15 C16 1.364(4) . ? C16 C17 1.379(4) . ? C17 C18 1.376(3) . ? 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 C18 O1 C1 119.0(2) . . ? O1 C1 C2 107.7(2) . . ? O6 C2 C1 107.9(2) . . ? O6 C2 C3 107.4(2) . . ? C1 C2 C3 115.7(2) . . ? O2 C3 C2 107.1(2) . . ? C4 O2 C3 119.1(2) . . ? O2 C4 C5 125.3(3) . . ? O2 C4 C9 114.7(2) . . ? C5 C4 C9 120.0(3) . . ? C4 C5 C6 119.5(3) . . ? C7 C6 C5 120.9(3) . . ? C6 C7 C8 120.0(3) . . ? C9 C8 C7 119.7(3) . . ? O3 C9 C8 124.9(2) . . ? O3 C9 C4 115.2(2) . . ? C8 C9 C4 119.9(2) . . ? C9 O3 C10 118.6(2) . . ? O3 C10 C11 107.7(2) . . ? O5 C11 C10 109.4(2) . . ? O5 C11 C12 110.5(2) . . ? C10 C11 C12 116.2(2) . . ? O4 C12 C11 107.4(2) . . ? C13 O4 C12 118.1(2) . . ? O4 C13 C14 125.6(2) . . ? O4 C13 C18 114.7(2) . . ? C14 C13 C18 119.6(2) . . ? C13 C14 C15 119.9(3) . . ? C16 C15 C14 120.0(3) . . ? C15 C16 C17 120.5(3) . . ? C18 C17 C16 120.0(3) . . ? O1 C18 C17 125.3(2) . . ? O1 C18 C13 114.9(2) . . ? C17 C18 C13 119.9(2) . . ? 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 C18 O1 C1 C2 -173.7(2) . . . . ? O1 C1 C2 O6 169.9(2) . . . . ? O1 C1 C2 C3 -69.8(3) . . . . ? O6 C2 C3 O2 -168.2(2) . . . . ? C1 C2 C3 O2 71.2(3) . . . . ? C2 C3 O2 C4 174.6(2) . . . . ? C3 O2 C4 C5 -3.4(4) . . . . ? C3 O2 C4 C9 176.2(2) . . . . ? O2 C4 C5 C6 179.2(3) . . . . ? C9 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 O3 179.6(2) . . . . ? C7 C8 C9 C4 -1.3(4) . . . . ? O2 C4 C9 O3 0.7(3) . . . . ? C5 C4 C9 O3 -179.7(2) . . . . ? O2 C4 C9 C8 -178.4(2) . . . . ? C5 C4 C9 C8 1.2(4) . . . . ? C8 C9 O3 C10 5.0(4) . . . . ? C4 C9 O3 C10 -174.1(2) . . . . ? C9 O3 C10 C11 -175.4(2) . . . . ? O3 C10 C11 O5 54.5(3) . . . . ? O3 C10 C11 C12 -71.5(3) . . . . ? O5 C11 C12 O4 -55.4(3) . . . . ? C10 C11 C12 O4 70.1(3) . . . . ? C11 C12 O4 C13 177.2(2) . . . . ? C12 O4 C13 C14 -5.5(4) . . . . ? C12 O4 C13 C18 173.3(2) . . . . ? O4 C13 C14 C15 179.6(3) . . . . ? C18 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? C1 O1 C18 C17 -0.8(4) . . . . ? C1 O1 C18 C13 179.9(2) . . . . ? C16 C17 C18 O1 179.8(3) . . . . ? C16 C17 C18 C13 -0.9(4) . . . . ? O4 C13 C18 O1 0.5(3) . . . . ? C14 C13 C18 O1 179.4(2) . . . . ? O4 C13 C18 C17 -178.9(2) . . . . ? C14 C13 C18 C17 0.0(4) . . . . ? _refine_diff_density_max 0.283 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.039 #===END data_COMPOUND10 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H22 O5' _chemical_formula_weight 330.37 _chemical_melting_point ? _chemical_compound_source ? 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 17.160(3) _cell_length_b 4.8770(10) _cell_length_c 21.453(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.640(10) _cell_angle_gamma 90.00 _cell_volume 1657.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 4.9 _cell_measurement_theta_max 16.5 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method ? _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'BRUKER P4' _diffrn_measurement_method 'THETA 2THETA' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2272 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.1281 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 22.56 _reflns_number_total 2187 _reflns_number_observed 1021 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXSTL-PLUS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXLTL PC VERS. 5.03 (Sheldrick, 1994)' _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.9795P] 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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0052(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2187 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1758 _refine_ls_R_factor_obs 0.0669 _refine_ls_wR_factor_all 0.1560 _refine_ls_wR_factor_obs 0.1127 _refine_ls_goodness_of_fit_all 1.025 _refine_ls_goodness_of_fit_obs 1.153 _refine_ls_restrained_S_all 1.025 _refine_ls_restrained_S_obs 1.153 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1277(2) 0.2054(8) -0.0605(2) 0.0450(12) Uani 1 d . . C1 C 0.1122(3) 0.0327(13) -0.0129(3) 0.041(2) Uani 1 d . . H1A H 0.0991(3) 0.1450(13) 0.0185(3) 0.049 Uiso 1 d R . H1B H 0.0656(3) -0.0874(13) -0.0358(3) 0.049 Uiso 1 d R . C2 C 0.1909(4) -0.1315(12) 0.0251(3) 0.044(2) Uani 1 d . . H2A H 0.1764(4) -0.2686(12) 0.0509(3) 0.053 Uiso 1 d R . H2B H 0.2080(4) -0.2190(12) -0.0077(3) 0.053 Uiso 1 d R . C3 C 0.2655(3) 0.0283(13) 0.0730(3) 0.044(2) Uani 1 d . . H3A H 0.3085(3) -0.0960(13) 0.1002(3) 0.053 Uiso 1 d R . H3B H 0.2474(3) 0.1405(13) 0.1017(3) 0.053 Uiso 1 d R . O2 O 0.2978(2) 0.1986(9) 0.0344(2) 0.0427(11) Uani 1 d . . C4 C 0.3644(4) 0.3656(13) 0.0692(3) 0.038(2) Uani 1 d . . C5 C 0.4079(4) 0.3653(13) 0.1390(3) 0.046(2) Uani 1 d . . H5 H 0.3914(4) 0.2415(13) 0.1665(3) 0.056 Uiso 1 d R . C6 C 0.4746(4) 0.5470(15) 0.1688(3) 0.052(2) Uani 1 d . . H6 H 0.5039(4) 0.5481(15) 0.2169(3) 0.063 Uiso 1 d R . C7 C 0.4993(4) 0.7214(15) 0.1300(3) 0.053(2) Uani 1 d . . H7 H 0.5464(4) 0.8419(15) 0.1510(3) 0.064 Uiso 1 d R . C8 C 0.4558(4) 0.7249(14) 0.0604(3) 0.048(2) Uani 1 d . . H8 H 0.4729(4) 0.8499(14) 0.0335(3) 0.058 Uiso 1 d R . C9 C 0.3887(3) 0.5481(13) 0.0295(3) 0.039(2) Uani 1 d . . O3 O 0.3416(2) 0.5349(9) -0.0384(2) 0.0514(13) Uani 1 d . . C10 C 0.3543(4) 0.7407(14) -0.0807(3) 0.050(2) Uani 1 d . . H10A H 0.3427(4) 0.9183(14) -0.0670(3) 0.060 Uiso 1 d R . H10B H 0.4112(4) 0.7363(14) -0.0786(3) 0.060 Uiso 1 d R . C11 C 0.2916(4) 0.6787(16) -0.1522(3) 0.052(2) Uani 1 d . . H11 H 0.2925(4) 0.4864(16) -0.1614(3) 0.063 Uiso 1 d R . O5 O 0.3163(3) 0.8533(11) -0.1948(2) 0.073(2) Uani 1 d . . C19 C 0.3003(5) 0.7228(23) -0.2587(3) 0.105(3) Uani 1 d G . H19A H 0.3212(36) 0.8436(110) -0.2841(31) 0.157 Uiso 1 calc G . H19B H 0.2409(8) 0.6946(135) -0.2828(30) 0.157 Uiso 1 calc G . H19C H 0.3292(36) 0.5500(66) -0.2525(38) 0.157 Uiso 1 calc G . C12 C 0.2001(4) 0.7544(14) -0.1633(3) 0.049(2) Uani 1 d . . H12A H 0.1666(4) 0.7753(14) -0.2106(3) 0.059 Uiso 1 d R . H12B H 0.1993(4) 0.9223(14) -0.1402(3) 0.059 Uiso 1 d R . O4 O 0.1682(2) 0.5351(9) -0.1360(2) 0.0484(12) Uani 1 d . . C13 C 0.0865(4) 0.5567(13) -0.1407(3) 0.038(2) Uani 1 d . . C14 C 0.0274(4) 0.7365(13) -0.1817(3) 0.047(2) Uani 1 d . . H14 H 0.0425(4) 0.8623(13) -0.2096(3) 0.056 Uiso 1 d R . C15 C -0.0550(4) 0.7383(15) -0.1835(3) 0.053(2) Uani 1 d . . H15 H -0.0965(4) 0.8606(15) -0.2133(3) 0.063 Uiso 1 d R . C16 C -0.0765(4) 0.5610(15) -0.1428(3) 0.054(2) Uani 1 d . . H16 H -0.1325(4) 0.5656(15) -0.1431(3) 0.065 Uiso 1 d R . C17 C -0.0173(4) 0.3782(14) -0.1008(3) 0.048(2) Uani 1 d . . H17 H -0.0332(4) 0.2526(14) -0.0733(3) 0.058 Uiso 1 d R . C18 C 0.0640(4) 0.3755(13) -0.0994(3) 0.036(2) Uani 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 O1 0.042(3) 0.046(3) 0.050(2) 0.015(2) 0.020(2) -0.002(2) C1 0.044(4) 0.039(4) 0.041(4) 0.000(3) 0.018(3) 0.001(3) C2 0.055(4) 0.038(4) 0.046(4) 0.007(3) 0.025(3) -0.007(4) C3 0.045(4) 0.049(4) 0.039(4) 0.007(4) 0.017(3) 0.003(4) O2 0.047(3) 0.046(3) 0.033(2) 0.008(2) 0.013(2) -0.010(2) C4 0.037(4) 0.033(4) 0.042(4) -0.002(3) 0.012(3) 0.004(3) C5 0.052(4) 0.048(4) 0.037(4) 0.006(4) 0.015(3) 0.002(4) C6 0.049(4) 0.062(5) 0.037(4) -0.006(4) 0.006(3) 0.001(4) C7 0.038(4) 0.057(5) 0.055(4) -0.010(4) 0.008(3) -0.005(4) C8 0.040(4) 0.051(5) 0.053(4) 0.004(4) 0.018(3) -0.009(4) C9 0.034(4) 0.039(4) 0.037(4) 0.002(3) 0.007(3) 0.001(3) O3 0.054(3) 0.061(3) 0.034(2) 0.005(2) 0.012(2) -0.016(3) C10 0.041(4) 0.063(5) 0.052(4) 0.005(4) 0.023(3) -0.010(4) C11 0.048(4) 0.080(6) 0.039(4) 0.014(4) 0.028(3) -0.021(4) O5 0.077(3) 0.095(4) 0.052(3) 0.004(3) 0.031(3) -0.026(3) C19 0.090(6) 0.194(11) 0.038(4) -0.008(6) 0.034(4) 0.011(7) C12 0.056(4) 0.056(5) 0.040(3) 0.005(4) 0.023(3) -0.010(4) O4 0.042(3) 0.054(3) 0.053(3) 0.018(2) 0.022(2) -0.001(2) C13 0.033(4) 0.042(4) 0.039(4) -0.004(4) 0.012(3) 0.000(4) C14 0.050(4) 0.044(4) 0.044(4) 0.004(4) 0.016(3) -0.002(4) C15 0.044(4) 0.060(5) 0.045(4) 0.002(4) 0.007(3) 0.013(4) C16 0.040(4) 0.060(5) 0.058(4) -0.005(4) 0.015(4) 0.003(4) C17 0.041(4) 0.048(5) 0.057(4) 0.001(4) 0.022(3) -0.003(4) C18 0.035(4) 0.040(4) 0.031(3) -0.006(3) 0.011(3) -0.007(3) _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 C18 1.369(6) . ? O1 C1 1.426(6) . ? C1 C2 1.510(7) . ? C2 C3 1.513(7) . ? C3 O2 1.427(6) . ? O2 C4 1.368(6) . ? C4 C5 1.391(7) . ? C4 C9 1.402(7) . ? C5 C6 1.393(8) . ? C6 C7 1.365(8) . ? C7 C8 1.389(7) . ? C8 C9 1.386(7) . ? C9 O3 1.370(6) . ? O3 C10 1.425(6) . ? C10 C11 1.527(7) . ? C11 O5 1.427(6) . ? C11 C12 1.540(7) . ? O5 C19 1.439(7) . ? C12 O4 1.426(6) . ? O4 C13 1.370(6) . ? C13 C14 1.373(7) . ? C13 C18 1.407(7) . ? C14 C15 1.400(7) . ? C15 C16 1.375(8) . ? C16 C17 1.390(8) . ? C17 C18 1.385(7) . ? 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 C18 O1 C1 118.0(4) . . ? O1 C1 C2 109.0(5) . . ? C1 C2 C3 116.1(5) . . ? O2 C3 C2 108.7(4) . . ? C4 O2 C3 117.4(4) . . ? O2 C4 C5 125.2(6) . . ? O2 C4 C9 115.3(5) . . ? C5 C4 C9 119.5(6) . . ? C4 C5 C6 119.9(6) . . ? C7 C6 C5 120.6(6) . . ? C6 C7 C8 119.9(6) . . ? C9 C8 C7 120.7(6) . . ? O3 C9 C8 125.5(6) . . ? O3 C9 C4 115.1(5) . . ? C8 C9 C4 119.4(5) . . ? C9 O3 C10 118.2(5) . . ? O3 C10 C11 106.2(5) . . ? O5 C11 C10 104.9(5) . . ? O5 C11 C12 107.1(5) . . ? C10 C11 C12 113.0(5) . . ? C11 O5 C19 110.6(6) . . ? O4 C12 C11 106.7(5) . . ? C13 O4 C12 117.1(5) . . ? O4 C13 C14 125.4(6) . . ? O4 C13 C18 115.2(5) . . ? C14 C13 C18 119.4(6) . . ? C13 C14 C15 120.7(6) . . ? C16 C15 C14 119.5(6) . . ? C15 C16 C17 120.5(6) . . ? C18 C17 C16 119.9(6) . . ? O1 C18 C17 125.5(6) . . ? O1 C18 C13 114.6(5) . . ? C17 C18 C13 119.9(6) . . ? 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 C18 O1 C1 C2 -178.8(4) . . . . ? O1 C1 C2 C3 69.1(6) . . . . ? C1 C2 C3 O2 -69.6(6) . . . . ? C2 C3 O2 C4 178.2(5) . . . . ? C3 O2 C4 C5 6.0(8) . . . . ? C3 O2 C4 C9 -174.0(5) . . . . ? O2 C4 C5 C6 -179.5(6) . . . . ? C9 C4 C5 C6 0.4(9) . . . . ? C4 C5 C6 C7 -1.6(9) . . . . ? C5 C6 C7 C8 2.2(10) . . . . ? C6 C7 C8 C9 -1.6(10) . . . . ? C7 C8 C9 O3 179.8(6) . . . . ? C7 C8 C9 C4 0.5(9) . . . . ? O2 C4 C9 O3 0.7(7) . . . . ? C5 C4 C9 O3 -179.3(5) . . . . ? O2 C4 C9 C8 -179.9(5) . . . . ? C5 C4 C9 C8 0.1(9) . . . . ? C8 C9 O3 C10 -8.6(8) . . . . ? C4 C9 O3 C10 170.8(5) . . . . ? C9 O3 C10 C11 -178.0(5) . . . . ? O3 C10 C11 O5 -169.4(5) . . . . ? O3 C10 C11 C12 74.3(7) . . . . ? C10 C11 O5 C19 146.7(6) . . . . ? C12 C11 O5 C19 -93.0(6) . . . . ? O5 C11 C12 O4 164.3(5) . . . . ? C10 C11 C12 O4 -80.7(6) . . . . ? C11 C12 O4 C13 -179.4(5) . . . . ? C12 O4 C13 C14 15.1(8) . . . . ? C12 O4 C13 C18 -164.9(5) . . . . ? O4 C13 C14 C15 178.9(6) . . . . ? C18 C13 C14 C15 -1.0(9) . . . . ? C13 C14 C15 C16 1.1(9) . . . . ? C14 C15 C16 C17 -0.9(10) . . . . ? C15 C16 C17 C18 0.5(9) . . . . ? C1 O1 C18 C17 -6.1(8) . . . . ? C1 O1 C18 C13 174.6(5) . . . . ? C16 C17 C18 O1 -179.8(5) . . . . ? C16 C17 C18 C13 -0.4(9) . . . . ? O4 C13 C18 O1 0.1(7) . . . . ? C14 C13 C18 O1 -179.9(5) . . . . ? O4 C13 C18 C17 -179.3(5) . . . . ? C14 C13 C18 C17 0.7(9) . . . . ? _refine_diff_density_max 0.320 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.050 #===END data_COMPOUND11 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H24 O5' _chemical_formula_weight 344.39 _chemical_melting_point ? _chemical_compound_source ? 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 20.295(6) _cell_length_b 8.139(3) _cell_length_c 11.205(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.19(2) _cell_angle_gamma 90.00 _cell_volume 1815.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 6.2 _cell_measurement_theta_max 10.2 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method ? _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'BRUKER P4' _diffrn_measurement_method 'THETA 2-THETA' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2526 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2345 _reflns_number_observed 1128 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'BRUKER SOFTWARE' _computing_cell_refinement SAME _computing_data_reduction SAME _computing_structure_solution 'SHELXTL PC VERS.5.03 (Sheldrick, 1994)' _computing_structure_refinement SAME _computing_molecular_graphics SAME _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.8891P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2343 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1595 _refine_ls_R_factor_obs 0.0676 _refine_ls_wR_factor_all 0.1747 _refine_ls_wR_factor_obs 0.1264 _refine_ls_goodness_of_fit_all 1.032 _refine_ls_goodness_of_fit_obs 1.163 _refine_ls_restrained_S_all 1.056 _refine_ls_restrained_S_obs 1.163 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2447(2) 0.6187(5) 0.3047(3) 0.0832(13) Uani 1 d . . O2 O 0.3852(3) 0.4926(6) 0.4800(5) 0.122(2) Uani 1 d . . O3 O 0.3067(2) 0.3114(5) 0.5790(3) 0.0810(12) Uani 1 d . . O4 O 0.1655(2) 0.4966(4) 0.4552(3) 0.0669(11) Uani 1 d . . O5 O 0.1376(2) 0.2067(5) 0.5771(3) 0.0831(12) Uani 1 d . . C1 C 0.2926(4) 0.7174(8) 0.2612(5) 0.092(2) Uani 1 d . . H1A H 0.2932(4) 0.8271(8) 0.2952(5) 0.110 Uiso 1 calc R . H1B H 0.2812(4) 0.7259(8) 0.1733(5) 0.110 Uiso 1 calc R . C2 C 0.3600(4) 0.6384(8) 0.2990(7) 0.104(2) Uani 1 d . . H2A H 0.3568(4) 0.5262(8) 0.2693(7) 0.125 Uiso 1 calc R . H2B H 0.3915(4) 0.6954(8) 0.2587(7) 0.125 Uiso 1 calc R . C3 C 0.3883(5) 0.6346(11) 0.4306(8) 0.158(4) Uani 1 d . . H3A H 0.4350(5) 0.6686(11) 0.4433(8) 0.189 Uiso 1 calc R . H3B H 0.3645(5) 0.7136(11) 0.4712(8) 0.189 Uiso 1 calc R . C4 C 0.4033(3) 0.4713(7) 0.6026(7) 0.082(2) Uani 1 d . . C5 C 0.4603(4) 0.5356(10) 0.6736(9) 0.125(3) Uani 1 d . . H5A H 0.4893(4) 0.5991(10) 0.6379(9) 0.150 Uiso 1 calc R . C6 C 0.4749(4) 0.5072(12) 0.7964(10) 0.130(3) Uani 1 d . . H6A H 0.5141(4) 0.5496(12) 0.8432(10) 0.156 Uiso 1 calc R . C7 C 0.4321(5) 0.4168(10) 0.8503(7) 0.111(3) Uani 1 d . . H7A H 0.4417(5) 0.4002(10) 0.9340(7) 0.134 Uiso 1 calc R . C8 C 0.3743(3) 0.3496(7) 0.7808(6) 0.087(2) Uani 1 d . . H8A H 0.3454(3) 0.2869(7) 0.8173(6) 0.104 Uiso 1 calc R . C9 C 0.3600(3) 0.3769(7) 0.6567(5) 0.068(2) Uani 1 d . . C10 C 0.2475(3) 0.2786(7) 0.6241(4) 0.065(2) Uani 1 d . . H10A H 0.2324(3) 0.3776(7) 0.6588(4) 0.078 Uiso 1 calc R . H10B H 0.2563(3) 0.1954(7) 0.6871(4) 0.078 Uiso 1 calc R . C11 C 0.1944(3) 0.2192(6) 0.5198(4) 0.0562(14) Uani 1 d . . C12 C 0.1831(3) 0.3391(6) 0.4147(4) 0.0637(15) Uani 1 d . . H12A H 0.2237(3) 0.3483(6) 0.3815(4) 0.076 Uiso 1 calc R . H12B H 0.1474(3) 0.2992(6) 0.3509(4) 0.076 Uiso 1 calc R . C13 C 0.1406(4) 0.6077(7) 0.3633(5) 0.068(2) Uani 1 d . . C14 C 0.0753(4) 0.6581(8) 0.3534(5) 0.086(2) Uani 1 d . . H14A H 0.0487(4) 0.6111(8) 0.4030(5) 0.104 Uiso 1 calc R . C15 C 0.0486(4) 0.7781(10) 0.2703(6) 0.105(2) Uani 1 d . . H15A H 0.0045(4) 0.8130(10) 0.2646(6) 0.125 Uiso 1 calc R . C16 C 0.0882(5) 0.8448(9) 0.1964(6) 0.102(2) Uani 1 d . . H16A H 0.0708(5) 0.9258(9) 0.1406(6) 0.122 Uiso 1 calc R . C17 C 0.1527(4) 0.7937(7) 0.2040(5) 0.085(2) Uani 1 d . . H17A H 0.1785(4) 0.8382(7) 0.1519(5) 0.101 Uiso 1 calc R . C18 C 0.1805(4) 0.6758(7) 0.2887(5) 0.072(2) Uani 1 d . . C19 C 0.2149(3) 0.0553(7) 0.4735(5) 0.081(2) Uani 1 d . . H19A H 0.1800(3) 0.0272(7) 0.4055(5) 0.121 Uiso 1 d R . H19B H 0.2200(3) -0.0351(7) 0.5369(5) 0.121 Uiso 1 d R . H19C H 0.2599(3) 0.0625(7) 0.4552(5) 0.121 Uiso 1 d R . C20 C 0.0798(4) 0.1343(11) 0.5114(7) 0.133(3) Uani 1 d G . H20A H 0.0448(23) 0.1175(79) 0.5568(51) 0.199 Uiso 1 calc G . H20B H 0.0618(31) 0.1908(71) 0.4370(33) 0.199 Uiso 1 calc G . H20C H 0.0976(33) 0.0300(41) 0.4931(55) 0.199 Uiso 1 calc G . 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 0.102(3) 0.067(3) 0.087(3) 0.017(2) 0.035(3) -0.013(3) O2 0.206(6) 0.086(4) 0.086(3) -0.010(3) 0.060(4) -0.051(4) O3 0.080(3) 0.110(3) 0.056(2) -0.011(2) 0.019(2) -0.030(2) O4 0.103(3) 0.057(2) 0.044(2) -0.002(2) 0.022(2) 0.002(2) O5 0.087(3) 0.097(3) 0.072(2) 0.007(2) 0.031(2) -0.016(3) C1 0.128(6) 0.077(5) 0.076(4) 0.012(4) 0.031(4) -0.028(5) C2 0.113(6) 0.082(5) 0.126(6) 0.000(5) 0.043(5) -0.020(5) C3 0.209(10) 0.098(7) 0.136(8) -0.005(6) -0.040(7) -0.008(7) C4 0.082(5) 0.067(4) 0.098(5) -0.024(4) 0.021(4) -0.013(4) C5 0.110(7) 0.121(7) 0.150(8) -0.053(7) 0.042(6) -0.040(5) C6 0.084(6) 0.144(9) 0.149(9) -0.057(8) -0.006(6) 0.001(6) C7 0.114(7) 0.113(7) 0.087(5) -0.018(5) -0.029(5) 0.034(5) C8 0.101(5) 0.075(5) 0.075(5) 0.000(4) -0.006(4) 0.004(4) C9 0.081(4) 0.053(4) 0.067(4) -0.007(3) 0.010(4) -0.002(3) C10 0.078(4) 0.068(4) 0.052(3) 0.000(3) 0.022(3) -0.006(3) C11 0.069(4) 0.055(4) 0.048(3) -0.002(3) 0.021(3) -0.014(3) C12 0.088(4) 0.054(3) 0.050(3) -0.009(3) 0.016(3) -0.002(3) C13 0.097(5) 0.063(4) 0.044(3) -0.004(3) 0.012(4) 0.003(4) C14 0.111(6) 0.093(5) 0.055(4) 0.001(4) 0.018(4) 0.007(5) C15 0.112(6) 0.134(7) 0.060(4) 0.004(5) 0.000(4) 0.032(5) C16 0.149(7) 0.092(6) 0.054(4) 0.000(4) -0.007(5) 0.023(6) C17 0.136(6) 0.064(4) 0.053(4) 0.010(3) 0.015(4) -0.005(4) C18 0.105(6) 0.053(4) 0.059(4) -0.003(3) 0.018(4) -0.006(4) C19 0.101(5) 0.064(4) 0.078(4) -0.016(3) 0.021(3) -0.006(3) C20 0.079(5) 0.198(9) 0.120(6) -0.008(6) 0.014(5) -0.036(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 O1 C18 1.362(6) . ? O1 C1 1.419(6) . ? O2 C3 1.289(8) . ? O2 C4 1.362(7) . ? O3 C9 1.358(6) . ? O3 C10 1.416(5) . ? O4 C13 1.390(6) . ? O4 C12 1.428(5) . ? O5 C20 1.389(7) . ? O5 C11 1.429(5) . ? C1 C2 1.496(8) . ? C2 C3 1.475(9) . ? C4 C5 1.374(8) . ? C4 C9 1.392(7) . ? C5 C6 1.369(10) . ? C6 C7 1.366(10) . ? C7 C8 1.388(9) . ? C8 C9 1.382(7) . ? C10 C11 1.507(6) . ? C11 C12 1.512(6) . ? C11 C19 1.519(7) . ? C13 C14 1.370(7) . ? C13 C18 1.388(7) . ? C14 C15 1.385(8) . ? C15 C16 1.373(9) . ? C16 C17 1.361(9) . ? C17 C18 1.390(7) . ? 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 C18 O1 C1 117.6(5) . . ? C3 O2 C4 121.4(6) . . ? C9 O3 C10 118.1(4) . . ? C13 O4 C12 115.3(4) . . ? C20 O5 C11 117.7(5) . . ? O1 C1 C2 108.0(5) . . ? C3 C2 C1 116.7(7) . . ? O2 C3 C2 114.0(7) . . ? O2 C4 C5 124.6(7) . . ? O2 C4 C9 116.0(6) . . ? C5 C4 C9 119.3(7) . . ? C6 C5 C4 120.8(8) . . ? C7 C6 C5 120.2(9) . . ? C6 C7 C8 120.3(8) . . ? C9 C8 C7 119.4(7) . . ? O3 C9 C8 124.5(6) . . ? O3 C9 C4 115.4(6) . . ? C8 C9 C4 120.0(6) . . ? O3 C10 C11 108.2(4) . . ? O5 C11 C10 101.1(4) . . ? O5 C11 C12 112.5(4) . . ? C10 C11 C12 112.0(4) . . ? O5 C11 C19 112.9(4) . . ? C10 C11 C19 110.2(4) . . ? C12 C11 C19 108.1(4) . . ? O4 C12 C11 110.0(4) . . ? C14 C13 C18 120.0(6) . . ? C14 C13 O4 117.5(6) . . ? C18 C13 O4 122.3(6) . . ? C13 C14 C15 120.8(7) . . ? C16 C15 C14 119.0(7) . . ? C17 C16 C15 120.7(7) . . ? C16 C17 C18 120.8(7) . . ? O1 C18 C13 116.1(6) . . ? O1 C18 C17 125.2(6) . . ? C13 C18 C17 118.7(7) . . ? 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 C18 O1 C1 C2 174.7(5) . . . . ? O1 C1 C2 C3 -66.9(8) . . . . ? C4 O2 C3 C2 -173.8(6) . . . . ? C1 C2 C3 O2 104.6(9) . . . . ? C3 O2 C4 C5 -45.2(11) . . . . ? C3 O2 C4 C9 135.0(8) . . . . ? O2 C4 C5 C6 -179.6(7) . . . . ? C9 C4 C5 C6 0.2(11) . . . . ? C4 C5 C6 C7 -1.3(13) . . . . ? C5 C6 C7 C8 1.6(13) . . . . ? C6 C7 C8 C9 -0.9(11) . . . . ? C10 O3 C9 C8 30.0(8) . . . . ? C10 O3 C9 C4 -152.8(5) . . . . ? C7 C8 C9 O3 176.9(6) . . . . ? C7 C8 C9 C4 -0.2(9) . . . . ? O2 C4 C9 O3 3.0(8) . . . . ? C5 C4 C9 O3 -176.9(6) . . . . ? O2 C4 C9 C8 -179.6(5) . . . . ? C5 C4 C9 C8 0.5(9) . . . . ? C9 O3 C10 C11 175.8(4) . . . . ? C20 O5 C11 C10 -172.1(6) . . . . ? C20 O5 C11 C12 68.3(7) . . . . ? C20 O5 C11 C19 -54.4(7) . . . . ? O3 C10 C11 O5 -175.0(4) . . . . ? O3 C10 C11 C12 -55.0(6) . . . . ? O3 C10 C11 C19 65.4(5) . . . . ? C13 O4 C12 C11 -167.4(5) . . . . ? O5 C11 C12 O4 56.2(5) . . . . ? C10 C11 C12 O4 -56.9(6) . . . . ? C19 C11 C12 O4 -178.4(4) . . . . ? C12 O4 C13 C14 115.4(5) . . . . ? C12 O4 C13 C18 -69.0(6) . . . . ? C18 C13 C14 C15 -0.7(9) . . . . ? O4 C13 C14 C15 175.0(5) . . . . ? C13 C14 C15 C16 0.9(10) . . . . ? C14 C15 C16 C17 0.3(10) . . . . ? C15 C16 C17 C18 -1.6(10) . . . . ? C1 O1 C18 C13 -160.1(5) . . . . ? C1 O1 C18 C17 20.5(8) . . . . ? C14 C13 C18 O1 180.0(5) . . . . ? O4 C13 C18 O1 4.5(7) . . . . ? C14 C13 C18 C17 -0.5(8) . . . . ? O4 C13 C18 C17 -176.0(5) . . . . ? C16 C17 C18 O1 -178.9(6) . . . . ? C16 C17 C18 C13 1.7(8) . . . . ? _refine_diff_density_max 0.164 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.036