# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Tomas Martin' 'Romen Carrillo' 'Matias Lopez-Rodriguez' 'Victor S. Martin' _publ_contact_author_name 'Tomas Martin' _publ_contact_author_address ; Qu mica Biol\'ogica y Biotecnolog a Instituto de Productos Naurales y Agrobiolog a-CSIC Avenida Francisco S\'anchez, 3 La Laguna Santa Cruz de Tenerife 38206 SPAIN ; _publ_contact_author_email TMARTIN@IPNA.CSIC.ES data_DIMER-4 _database_code_depnum_ccdc_archive 'CCDC 266195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O8' _chemical_formula_weight 344.35 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 0.0000 '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 0.0000 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.546(7) _cell_length_b 4.490(1) _cell_length_c 14.124(7) _cell_angle_alpha 90.00 _cell_angle_beta 125.50(13) _cell_angle_gamma 90.00 _cell_volume 854(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Enraf-Nonius KappaCCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1113 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.94 _reflns_number_total 1113 _reflns_number_gt 1020 _reflns_threshold_expression >4sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et atl, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material ? _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^)+(0.1060P)^2^+0.0205P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.30(4) _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(10) _refine_ls_number_reflns 1113 _refine_ls_number_parameters 110 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_restrained_S_all 1.260 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 1.06502(14) 0.3846(6) 0.76216(15) 0.0504(7) Uani 1 1 d . . . O2 O 0.87762(12) 0.4382(5) 0.81953(14) 0.0384(6) Uani 1 1 d . . . O3 O 0.75179(17) 0.1095(7) 0.72155(19) 0.0632(8) Uani 1 1 d . . . O4 O 0.83819(13) 0.5276(6) 0.97931(14) 0.0433(6) Uani 1 1 d . . . C1 C 1.02318(17) 0.4532(7) 0.8238(2) 0.0368(7) Uani 1 1 d . . . H1 H 1.0239 0.6698 0.8329 0.044 Uiso 1 1 calc R . . C2 C 0.91533(17) 0.3440(7) 0.75374(19) 0.0358(7) Uani 1 1 d . . . H2 H 0.9140 0.1261 0.7489 0.043 Uiso 1 1 calc R . . C3 C 0.8546(2) 0.4751(8) 0.6318(2) 0.0441(8) Uani 1 1 d . . . H3A H 0.8458 0.6872 0.6359 0.053 Uiso 1 1 calc R . . H3B H 0.7895 0.3830 0.5862 0.053 Uiso 1 1 calc R . . C4 C 0.9071(2) 0.4223(12) 0.5731(2) 0.0574(10) Uani 1 1 d . . . H4A H 0.9059 0.2116 0.5571 0.069 Uiso 1 1 calc R . . H4B H 0.8726 0.5286 0.4997 0.069 Uiso 1 1 calc R . . C5 C 1.0139(2) 0.5295(14) 0.6512(3) 0.0654(12) Uani 1 1 d . . . H5A H 1.0474 0.4871 0.6148 0.079 Uiso 1 1 calc R . . H5B H 1.0149 0.7432 0.6617 0.079 Uiso 1 1 calc R . . C6 C 0.79578(19) 0.2963(8) 0.7956(2) 0.0423(7) Uani 1 1 d . . . C7 C 0.76315(18) 0.4024(10) 0.8705(2) 0.0477(8) Uani 1 1 d . . . H7A H 0.7112 0.5499 0.8268 0.057 Uiso 1 1 calc R . . H7B H 0.7342 0.2349 0.8843 0.057 Uiso 1 1 calc R . . C8 C 0.91013(19) 0.3125(7) 1.0570(2) 0.0389(7) Uani 1 1 d . . . H8A H 0.9492 0.2495 1.0295 0.047 Uiso 1 1 calc R . . H8B H 0.8772 0.1390 1.0609 0.047 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 0.0314(10) 0.0873(19) 0.0320(10) 0.0111(12) 0.0180(8) 0.0092(12) O2 0.0274(9) 0.0519(12) 0.0326(9) -0.0092(9) 0.0155(7) -0.0033(9) O3 0.0449(12) 0.092(2) 0.0509(12) -0.0287(14) 0.0270(10) -0.0304(14) O4 0.0301(10) 0.0592(13) 0.0288(9) -0.0052(9) 0.0104(8) 0.0076(9) C1 0.0259(11) 0.0489(16) 0.0282(11) 0.0027(12) 0.0114(9) 0.0011(12) C2 0.0268(11) 0.0476(16) 0.0276(12) -0.0046(11) 0.0127(10) 0.0015(11) C3 0.0278(12) 0.062(2) 0.0283(11) 0.0006(13) 0.0079(10) 0.0023(12) C4 0.0433(15) 0.090(3) 0.0307(12) 0.0097(17) 0.0167(12) 0.013(2) C5 0.0398(15) 0.118(4) 0.0361(15) 0.022(2) 0.0205(13) 0.003(2) C6 0.0232(11) 0.0651(19) 0.0288(12) -0.0036(13) 0.0095(10) -0.0010(13) C7 0.0227(12) 0.080(2) 0.0298(12) -0.0070(15) 0.0090(10) 0.0011(15) C8 0.0284(12) 0.0499(16) 0.0313(12) -0.0014(12) 0.0133(10) 0.0015(12) _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 C1 1.425(6) . ? O1 C5 1.433(7) . ? O2 C6 1.350(6) . ? O2 C2 1.451(6) . ? O3 C6 1.201(5) . ? O4 C7 1.416(6) . ? O4 C8 1.427(5) . ? C1 C8 1.515(7) 2_757 ? C1 C2 1.534(7) . ? C1 H1 0.9800 . ? C2 C3 1.520(8) . ? C2 H2 0.9800 . ? C3 C4 1.529(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.518(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.517(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C1 1.515(7) 2_757 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C1 O1 C5 112.4(4) . . ? C6 O2 C2 116.4(3) . . ? C7 O4 C8 112.3(3) . . ? O1 C1 C8 106.9(4) . 2_757 ? O1 C1 C2 109.4(4) . . ? C8 C1 C2 114.0(3) 2_757 . ? O1 C1 H1 108.8 . . ? C8 C1 H1 108.8 2_757 . ? C2 C1 H1 108.8 . . ? O2 C2 C3 111.4(4) . . ? O2 C2 C1 105.4(4) . . ? C3 C2 C1 111.3(3) . . ? O2 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? C2 C3 C4 110.1(4) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.1(5) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O1 C5 C4 110.5(4) . . ? O1 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? O1 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? O3 C6 O2 124.1(3) . . ? O3 C6 C7 123.0(4) . . ? O2 C6 C7 112.9(3) . . ? O4 C7 C6 116.0(4) . . ? O4 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? O4 C7 H7B 108.3 . . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O4 C8 C1 108.4(3) . 2_757 ? O4 C8 H8A 110.0 . . ? C1 C8 H8A 110.0 2_757 . ? O4 C8 H8B 110.0 . . ? C1 C8 H8B 110.0 2_757 . ? H8A C8 H8B 108.4 . . ? 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 C5 O1 C1 C8 -174.4(3) . . . 2_757 ? C5 O1 C1 C2 61.6(4) . . . . ? C6 O2 C2 C3 78.2(4) . . . . ? C6 O2 C2 C1 -161.0(2) . . . . ? O1 C1 C2 O2 -176.8(2) . . . . ? C8 C1 C2 O2 63.5(4) 2_757 . . . ? O1 C1 C2 C3 -55.9(4) . . . . ? C8 C1 C2 C3 -175.5(3) 2_757 . . . ? O2 C2 C3 C4 169.2(3) . . . . ? C1 C2 C3 C4 51.8(4) . . . . ? C2 C3 C4 C5 -51.9(5) . . . . ? C1 O1 C5 C4 -63.0(5) . . . . ? C3 C4 C5 O1 56.7(6) . . . . ? C2 O2 C6 O3 -2.9(4) . . . . ? C2 O2 C6 C7 178.4(2) . . . . ? C8 O4 C7 C6 -67.4(4) . . . . ? O3 C6 C7 O4 156.2(3) . . . . ? O2 C6 C7 O4 -25.1(5) . . . . ? C7 O4 C8 C1 -170.7(2) . . . 2_757 ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.387 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.110 data_cis-TETRAMER(34) _database_code_depnum_ccdc_archive 'CCDC 266197' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H48 O16' _chemical_formula_weight 688.70 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.052(2) _cell_length_b 27.546(6) _cell_length_c 9.808(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.28(2) _cell_angle_gamma 90.00 _cell_volume 2211.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Enraf-Nonius KappaCCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4390 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4390 _reflns_number_gt 2579 _reflns_threshold_expression >4sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et atl., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L. Spek, 2003)' _computing_publication_material ? _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^)+(0.1830P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.15(2) _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(10) _refine_ls_number_reflns 4390 _refine_ls_number_parameters 434 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.2560 _refine_ls_wR_factor_gt 0.2360 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.5092(6) 0.36449(15) 0.1073(5) 0.0742(12) Uani 1 1 d . . . O2 O 0.4090(5) 0.39902(17) 0.3323(4) 0.0703(12) Uani 1 1 d . . . O3 O 0.4831(10) 0.4142(4) 0.5805(8) 0.175(5) Uani 1 1 d . . . O4 O 0.5129(9) 0.26615(19) 0.1869(11) 0.132(3) Uani 1 1 d . . . O21 O -0.0393(5) 0.43512(17) 0.6679(4) 0.0720(12) Uani 1 1 d . . . O22 O 0.0003(5) 0.33473(15) 0.7506(5) 0.0724(12) Uani 1 1 d . . . O23 O 0.1228(7) 0.2764(2) 0.9239(7) 0.118(2) Uani 1 1 d . . . O24 O 0.1596(8) 0.43254(18) 0.5212(7) 0.1015(18) Uani 1 1 d . . . O31 O -0.2303(5) 0.11953(14) 0.7584(4) 0.0630(11) Uani 1 1 d . . . O32 O 0.0276(5) 0.08240(16) 0.6831(4) 0.0655(11) Uani 1 1 d . . . O33 O 0.2988(6) 0.0686(3) 0.7609(6) 0.1049(19) Uani 1 1 d . . . O34 O -0.1325(7) 0.21522(16) 0.7768(8) 0.0970(17) Uani 1 1 d . . . O41 O 0.3505(5) 0.04664(15) 0.2349(5) 0.0674(11) Uani 1 1 d . . . O42 O 0.4683(5) 0.14463(15) 0.2785(5) 0.0675(12) Uani 1 1 d . . . O43 O 0.6776(9) 0.1949(3) 0.3820(8) 0.151(3) Uani 1 1 d . . . O44 O 0.2438(6) 0.04581(18) 0.4662(6) 0.0847(15) Uani 1 1 d . . . C1 C 0.5767(8) 0.3486(3) 0.2531(8) 0.0744(18) Uani 1 1 d . . . H1 H 0.6897 0.3387 0.2796 0.089 Uiso 1 1 calc R . . C2 C 0.5783(9) 0.3892(3) 0.3626(7) 0.081(2) Uani 1 1 d . . . H2 H 0.6398 0.3786 0.4673 0.097 Uiso 1 1 calc R . . C3 C 0.6543(10) 0.4370(3) 0.3328(8) 0.087(2) Uani 1 1 d . . . H3A H 0.6305 0.4641 0.3834 0.105 Uiso 1 1 calc R . . H3B H 0.7720 0.4336 0.3726 0.105 Uiso 1 1 calc R . . C4 C 0.5836(12) 0.4465(3) 0.1661(9) 0.098(2) Uani 1 1 d . . . H4A H 0.4694 0.4551 0.1310 0.118 Uiso 1 1 calc R . . H4B H 0.6396 0.4740 0.1479 0.118 Uiso 1 1 calc R . . C5 C 0.5966(9) 0.4047(3) 0.0775(8) 0.0820(19) Uani 1 1 d . . . H5A H 0.5480 0.4125 -0.0292 0.098 Uiso 1 1 calc R . . H5B H 0.7103 0.3961 0.1080 0.098 Uiso 1 1 calc R . . C6 C 0.3780(10) 0.4095(3) 0.4543(9) 0.084(2) Uani 1 1 d . . . C7 C 0.4820(11) 0.3044(3) 0.2645(11) 0.089(2) Uani 1 1 d . . . H7A H 0.5162 0.2956 0.3694 0.107 Uiso 1 1 calc R . . H7B H 0.3660 0.3115 0.2206 0.107 Uiso 1 1 calc R . . C8 C 0.4328(11) 0.2252(3) 0.1819(11) 0.101(3) Uani 1 1 d . . . H8A H 0.3907 0.2120 0.0807 0.122 Uiso 1 1 calc R . . H8B H 0.3403 0.2325 0.2038 0.122 Uiso 1 1 calc R . . C21 C 0.1125(8) 0.4103(2) 0.7319(7) 0.0634(15) Uani 1 1 d . . . H21 H 0.1959 0.4343 0.7888 0.076 Uiso 1 1 calc R . . C22 C 0.1181(7) 0.3714(2) 0.8418(6) 0.0578(14) Uani 1 1 d . . . H22 H 0.2278 0.3573 0.8903 0.069 Uiso 1 1 calc R . . C23 C 0.0658(10) 0.3905(3) 0.9607(7) 0.080(2) Uani 1 1 d . . . H23A H 0.0495 0.3635 1.0162 0.096 Uiso 1 1 calc R . . H23B H 0.1514 0.4110 1.0316 0.096 Uiso 1 1 calc R . . C24 C -0.0860(10) 0.4185(3) 0.8896(8) 0.090(2) Uani 1 1 d . . . H24A H -0.1087 0.4338 0.9677 0.108 Uiso 1 1 calc R . . H24B H -0.1753 0.3965 0.8344 0.108 Uiso 1 1 calc R . . C25 C -0.0790(11) 0.4596(3) 0.7764(9) 0.087(2) Uani 1 1 d . . . H25A H -0.1837 0.4759 0.7272 0.105 Uiso 1 1 calc R . . H25B H 0.0037 0.4836 0.8307 0.105 Uiso 1 1 calc R . . C26 C 0.0156(9) 0.2893(2) 0.8043(8) 0.0768(19) Uani 1 1 d . . . C27 C 0.1493(14) 0.3937(3) 0.6050(11) 0.104(3) Uani 1 1 d . . . H27A H 0.2519 0.3761 0.6450 0.125 Uiso 1 1 calc R . . H27B H 0.0641 0.3718 0.5408 0.125 Uiso 1 1 calc R . . C28 C 0.1923(14) 0.4154(4) 0.3945(12) 0.126(4) Uani 1 1 d . . . H28A H 0.1525 0.4388 0.3128 0.152 Uiso 1 1 calc R . . H28B H 0.1379 0.3847 0.3570 0.152 Uiso 1 1 calc R . . C31 C -0.0607(7) 0.1327(2) 0.8325(6) 0.0608(15) Uani 1 1 d . . . H31 H -0.0361 0.1420 0.9365 0.073 Uiso 1 1 calc R . . C32 C 0.0533(7) 0.0908(2) 0.8377(7) 0.0638(15) Uani 1 1 d . . . H32 H 0.1672 0.0999 0.8994 0.077 Uiso 1 1 calc R . . C33 C 0.0103(9) 0.0453(3) 0.9015(9) 0.092(2) Uani 1 1 d . . . H33A H 0.0698 0.0179 0.8877 0.111 Uiso 1 1 calc R . . H33B H 0.0444 0.0496 1.0089 0.111 Uiso 1 1 calc R . . C34 C -0.1697(10) 0.0343(3) 0.8271(9) 0.087(2) Uani 1 1 d . . . H34A H -0.1949 0.0076 0.8781 0.105 Uiso 1 1 calc R . . H34B H -0.2030 0.0254 0.7225 0.105 Uiso 1 1 calc R . . C35 C -0.2578(9) 0.0801(3) 0.8377(9) 0.086(2) Uani 1 1 d . . . H35A H -0.3741 0.0736 0.7968 0.104 Uiso 1 1 calc R . . H35B H -0.2207 0.0889 0.9429 0.104 Uiso 1 1 calc R . . C36 C 0.1640(8) 0.0700(2) 0.6619(8) 0.0660(16) Uani 1 1 d . . . C37 C -0.0378(8) 0.1763(3) 0.7536(8) 0.0712(17) Uani 1 1 d . . . H37A H 0.0768 0.1851 0.7948 0.085 Uiso 1 1 calc R . . H37B H -0.0757 0.1697 0.6468 0.085 Uiso 1 1 calc R . . C38 C -0.1241(11) 0.2603(3) 0.7004(11) 0.101(3) Uani 1 1 d . . . H38A H -0.2246 0.2785 0.6715 0.121 Uiso 1 1 calc R . . H38B H -0.1104 0.2527 0.6099 0.121 Uiso 1 1 calc R . . C41 C 0.4405(7) 0.0669(2) 0.3756(6) 0.0620(15) Uani 1 1 d . . . H41 H 0.5040 0.0411 0.4444 0.074 Uiso 1 1 calc R . . C42 C 0.5567(7) 0.1058(2) 0.3736(7) 0.0624(15) Uani 1 1 d . . . H42 H 0.6203 0.1180 0.4761 0.075 Uiso 1 1 calc R . . C43 C 0.6725(9) 0.0836(4) 0.3121(10) 0.101(3) Uani 1 1 d . . . H43A H 0.7474 0.0615 0.3863 0.122 Uiso 1 1 calc R . . H43B H 0.7366 0.1093 0.2958 0.122 Uiso 1 1 calc R . . C44 C 0.5754(10) 0.0555(3) 0.1593(9) 0.085(2) Uani 1 1 d . . . H44A H 0.5176 0.0784 0.0790 0.102 Uiso 1 1 calc R . . H44B H 0.6509 0.0373 0.1324 0.102 Uiso 1 1 calc R . . C45 C 0.4597(11) 0.0226(3) 0.1775(9) 0.092(2) Uani 1 1 d . . . H45A H 0.5197 -0.0031 0.2468 0.110 Uiso 1 1 calc R . . H45B H 0.3932 0.0076 0.0809 0.110 Uiso 1 1 calc R . . C46 C 0.5405(10) 0.1866(3) 0.2944(9) 0.089(2) Uani 1 1 d . . . C47 C 0.3139(8) 0.0865(2) 0.4300(8) 0.0742(18) Uani 1 1 d . . . H47A H 0.3672 0.1071 0.5179 0.089 Uiso 1 1 calc R . . H47B H 0.2305 0.1054 0.3511 0.089 Uiso 1 1 calc R . . C48 C 0.1123(9) 0.0568(3) 0.4974(8) 0.085(2) Uani 1 1 d . . . H48A H 0.0392 0.0291 0.4720 0.102 Uiso 1 1 calc R . . H48B H 0.0525 0.0838 0.4346 0.102 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 0.108(3) 0.052(2) 0.080(3) 0.007(2) 0.056(2) -0.006(2) O2 0.085(3) 0.083(3) 0.056(2) -0.006(2) 0.042(2) 0.003(2) O3 0.137(5) 0.317(14) 0.095(4) -0.105(6) 0.073(4) -0.080(7) O4 0.160(6) 0.052(3) 0.243(8) 0.010(4) 0.142(6) 0.010(3) O21 0.095(3) 0.074(3) 0.054(2) 0.008(2) 0.039(2) 0.009(2) O22 0.093(3) 0.049(2) 0.071(2) -0.005(2) 0.032(2) -0.010(2) O23 0.119(4) 0.072(3) 0.106(4) 0.013(3) -0.005(3) 0.020(3) O24 0.176(5) 0.059(3) 0.117(4) 0.005(3) 0.107(4) 0.016(3) O31 0.063(2) 0.059(2) 0.076(2) 0.012(2) 0.0386(19) 0.0035(19) O32 0.061(2) 0.082(3) 0.064(2) -0.003(2) 0.0365(18) 0.014(2) O33 0.055(3) 0.149(5) 0.101(3) 0.018(4) 0.024(3) 0.007(3) O34 0.121(4) 0.044(2) 0.150(5) 0.014(3) 0.081(4) 0.002(2) O41 0.080(3) 0.049(2) 0.080(3) -0.017(2) 0.041(2) -0.002(2) O42 0.059(2) 0.059(3) 0.073(2) 0.006(2) 0.0170(18) -0.0195(19) O43 0.137(6) 0.182(8) 0.116(5) 0.014(5) 0.036(4) -0.096(6) O44 0.099(3) 0.072(3) 0.122(4) 0.001(3) 0.085(3) 0.013(3) C1 0.068(4) 0.070(4) 0.087(5) 0.014(4) 0.034(3) 0.004(3) C2 0.085(5) 0.102(6) 0.052(3) 0.006(4) 0.026(3) -0.010(4) C3 0.102(5) 0.084(5) 0.074(4) -0.022(4) 0.035(4) -0.038(4) C4 0.137(7) 0.070(5) 0.083(5) 0.007(4) 0.044(5) -0.028(4) C5 0.088(4) 0.090(5) 0.072(4) -0.009(4) 0.039(3) -0.021(4) C6 0.103(5) 0.079(5) 0.089(5) 0.003(4) 0.058(4) -0.010(4) C7 0.114(6) 0.059(4) 0.124(6) 0.015(4) 0.079(5) 0.003(4) C8 0.123(6) 0.052(4) 0.130(7) 0.001(4) 0.055(5) 0.006(4) C21 0.084(4) 0.048(3) 0.069(3) 0.007(3) 0.042(3) 0.012(3) C22 0.055(3) 0.052(3) 0.068(3) -0.001(3) 0.029(3) -0.012(2) C23 0.117(6) 0.068(4) 0.047(3) -0.011(3) 0.026(3) -0.014(4) C24 0.112(6) 0.102(6) 0.066(4) -0.011(4) 0.047(4) 0.008(5) C25 0.121(6) 0.070(4) 0.089(5) 0.003(4) 0.062(4) 0.031(4) C26 0.107(5) 0.040(3) 0.072(4) -0.005(3) 0.028(4) 0.001(3) C27 0.166(8) 0.071(5) 0.125(6) 0.001(5) 0.110(6) 0.012(5) C28 0.167(9) 0.126(8) 0.137(8) 0.051(6) 0.114(7) 0.028(7) C31 0.067(3) 0.058(3) 0.057(3) -0.012(3) 0.027(3) -0.005(3) C32 0.062(3) 0.057(4) 0.065(3) 0.003(3) 0.020(3) 0.006(3) C33 0.087(5) 0.099(6) 0.090(5) 0.024(4) 0.037(4) 0.034(4) C34 0.110(6) 0.063(4) 0.084(4) 0.020(4) 0.037(4) -0.006(4) C35 0.081(4) 0.101(6) 0.090(4) 0.015(4) 0.049(4) 0.005(4) C36 0.077(4) 0.053(3) 0.093(4) 0.000(3) 0.060(4) -0.007(3) C37 0.075(4) 0.067(4) 0.090(4) 0.005(3) 0.054(4) -0.012(3) C38 0.132(7) 0.044(4) 0.124(6) 0.011(4) 0.053(5) -0.011(4) C41 0.071(4) 0.057(3) 0.059(3) 0.013(3) 0.029(3) 0.001(3) C42 0.060(3) 0.057(3) 0.063(3) 0.001(3) 0.019(3) 0.002(3) C43 0.072(4) 0.118(7) 0.126(6) 0.057(6) 0.054(4) 0.016(4) C44 0.100(5) 0.095(5) 0.082(5) 0.012(4) 0.061(4) 0.009(4) C45 0.120(6) 0.098(6) 0.091(5) -0.012(4) 0.077(5) -0.011(5) C46 0.093(5) 0.102(6) 0.077(4) 0.005(4) 0.041(4) -0.032(5) C47 0.072(4) 0.062(4) 0.097(5) 0.003(4) 0.044(3) -0.011(3) C48 0.073(4) 0.122(6) 0.080(4) -0.030(4) 0.051(3) 0.004(4) _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 C1 1.365(8) . ? O1 C5 1.461(8) . ? O2 C6 1.372(9) . ? O2 C2 1.456(9) . ? O3 C6 1.204(10) . ? O4 C8 1.330(10) . ? O4 C7 1.396(10) . ? O21 C21 1.419(7) . ? O21 C25 1.429(8) . ? O22 C26 1.342(8) . ? O22 C22 1.464(7) . ? O23 C26 1.213(8) . ? O24 C27 1.377(9) . ? O24 C28 1.472(11) . ? O31 C35 1.419(9) . ? O31 C31 1.437(7) . ? O32 C36 1.380(8) . ? O32 C32 1.451(7) . ? O33 C36 1.192(8) . ? O34 C37 1.451(9) . ? O34 C38 1.468(9) . ? O41 C41 1.385(7) . ? O41 C45 1.486(9) . ? O42 C46 1.306(9) . ? O42 C42 1.419(7) . ? O43 C46 1.191(10) . ? O44 C48 1.383(8) . ? O44 C47 1.406(8) . ? C1 C7 1.520(10) . ? C1 C2 1.547(11) . ? C1 H1 0.9800 . ? C2 C3 1.570(11) . ? C2 H2 0.9800 . ? C3 C4 1.503(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.477(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C28 1.534(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C46 1.542(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C21 C27 1.491(10) . ? C21 C22 1.506(8) . ? C21 H21 0.9800 . ? C22 C23 1.528(10) . ? C22 H22 0.9800 . ? C23 C24 1.466(11) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.607(11) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C38 1.475(11) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C31 C37 1.489(9) . ? C31 C32 1.536(8) . ? C31 H31 0.9800 . ? C32 C33 1.523(11) . ? C32 H32 0.9800 . ? C33 C34 1.504(12) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.518(11) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C48 1.519(10) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C41 C42 1.509(9) . ? C41 C47 1.554(10) . ? C41 H41 0.9800 . ? C42 C43 1.541(11) . ? C42 H42 0.9800 . ? C43 C44 1.580(13) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.453(11) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? 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 C1 O1 C5 114.5(5) . . ? C6 O2 C2 116.8(5) . . ? C8 O4 C7 115.3(7) . . ? C21 O21 C25 113.7(5) . . ? C26 O22 C22 118.5(5) . . ? C27 O24 C28 110.1(6) . . ? C35 O31 C31 108.4(5) . . ? C36 O32 C32 116.3(5) . . ? C37 O34 C38 112.5(6) . . ? C41 O41 C45 110.7(5) . . ? C46 O42 C42 118.4(5) . . ? C48 O44 C47 113.9(6) . . ? O1 C1 C7 108.7(6) . . ? O1 C1 C2 111.2(6) . . ? C7 C1 C2 111.5(6) . . ? O1 C1 H1 108.5 . . ? C7 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? O2 C2 C1 107.2(5) . . ? O2 C2 C3 108.2(6) . . ? C1 C2 C3 110.6(6) . . ? O2 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C4 C3 C2 109.4(5) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 113.6(7) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? O1 C5 C4 106.7(6) . . ? O1 C5 H5A 110.4 . . ? C4 C5 H5A 110.4 . . ? O1 C5 H5B 110.4 . . ? C4 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? O3 C6 O2 123.6(7) . . ? O3 C6 C28 129.6(8) . . ? O2 C6 C28 106.7(7) . . ? O4 C7 C1 108.3(6) . . ? O4 C7 H7A 110.0 . . ? C1 C7 H7A 110.0 . . ? O4 C7 H7B 110.0 . . ? C1 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? O4 C8 C46 112.9(8) . . ? O4 C8 H8A 109.0 . . ? C46 C8 H8A 109.0 . . ? O4 C8 H8B 109.0 . . ? C46 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O21 C21 C27 107.4(6) . . ? O21 C21 C22 112.9(5) . . ? C27 C21 C22 115.4(5) . . ? O21 C21 H21 106.9 . . ? C27 C21 H21 106.9 . . ? C22 C21 H21 106.9 . . ? O22 C22 C21 105.1(5) . . ? O22 C22 C23 108.8(5) . . ? C21 C22 C23 112.0(5) . . ? O22 C22 H22 110.3 . . ? C21 C22 H22 110.3 . . ? C23 C22 H22 110.3 . . ? C24 C23 C22 110.6(5) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 113.2(7) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? O21 C25 C24 106.1(6) . . ? O21 C25 H25A 110.5 . . ? C24 C25 H25A 110.5 . . ? O21 C25 H25B 110.5 . . ? C24 C25 H25B 110.5 . . ? H25A C25 H25B 108.7 . . ? O23 C26 O22 123.9(6) . . ? O23 C26 C38 127.2(6) . . ? O22 C26 C38 108.7(6) . . ? O24 C27 C21 110.9(6) . . ? O24 C27 H27A 109.5 . . ? C21 C27 H27A 109.5 . . ? O24 C27 H27B 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? O24 C28 C6 107.1(9) . . ? O24 C28 H28A 110.3 . . ? C6 C28 H28A 110.3 . . ? O24 C28 H28B 110.3 . . ? C6 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? O31 C31 C37 107.3(5) . . ? O31 C31 C32 112.6(5) . . ? C37 C31 C32 112.5(5) . . ? O31 C31 H31 108.1 . . ? C37 C31 H31 108.1 . . ? C32 C31 H31 108.1 . . ? O32 C32 C33 110.1(5) . . ? O32 C32 C31 106.2(4) . . ? C33 C32 C31 110.3(5) . . ? O32 C32 H32 110.0 . . ? C33 C32 H32 110.1 . . ? C31 C32 H32 110.0 . . ? C34 C33 C32 112.3(6) . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33B 109.1 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.9 . . ? C33 C34 C35 107.0(6) . . ? C33 C34 H34A 110.3 . . ? C35 C34 H34A 110.3 . . ? C33 C34 H34B 110.3 . . ? C35 C34 H34B 110.3 . . ? H34A C34 H34B 108.6 . . ? O31 C35 C34 112.2(5) . . ? O31 C35 H35A 109.2 . . ? C34 C35 H35A 109.2 . . ? O31 C35 H35B 109.2 . . ? C34 C35 H35B 109.2 . . ? H35A C35 H35B 107.9 . . ? O33 C36 O32 123.8(6) . . ? O33 C36 C48 127.0(6) . . ? O32 C36 C48 109.2(6) . . ? O34 C37 C31 107.0(5) . . ? O34 C37 H37A 110.3 . . ? C31 C37 H37A 110.3 . . ? O34 C37 H37B 110.3 . . ? C31 C37 H37B 110.3 . . ? H37A C37 H37B 108.6 . . ? O34 C38 C26 108.8(7) . . ? O34 C38 H38A 109.9 . . ? C26 C38 H38A 109.9 . . ? O34 C38 H38B 109.9 . . ? C26 C38 H38B 109.9 . . ? H38A C38 H38B 108.3 . . ? O41 C41 C42 113.0(5) . . ? O41 C41 C47 106.0(5) . . ? C42 C41 C47 112.2(5) . . ? O41 C41 H41 108.5 . . ? C42 C41 H41 108.5 . . ? C47 C41 H41 108.5 . . ? O42 C42 C41 110.1(4) . . ? O42 C42 C43 109.2(6) . . ? C41 C42 C43 108.5(6) . . ? O42 C42 H42 109.7 . . ? C41 C42 H42 109.7 . . ? C43 C42 H42 109.7 . . ? C42 C43 C44 111.7(6) . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43B 109.3 . . ? C44 C43 H43B 109.3 . . ? H43A C43 H43B 107.9 . . ? C45 C44 C43 109.1(6) . . ? C45 C44 H44A 109.9 . . ? C43 C44 H44A 109.9 . . ? C45 C44 H44B 109.9 . . ? C43 C44 H44B 109.9 . . ? H44A C44 H44B 108.3 . . ? C44 C45 O41 113.5(7) . . ? C44 C45 H45A 108.9 . . ? O41 C45 H45A 108.9 . . ? C44 C45 H45B 108.9 . . ? O41 C45 H45B 108.9 . . ? H45A C45 H45B 107.7 . . ? O43 C46 O42 124.7(8) . . ? O43 C46 C8 122.0(8) . . ? O42 C46 C8 113.2(7) . . ? O44 C47 C41 106.8(5) . . ? O44 C47 H47A 110.4 . . ? C41 C47 H47A 110.4 . . ? O44 C47 H47B 110.4 . . ? C41 C47 H47B 110.4 . . ? H47A C47 H47B 108.6 . . ? O44 C48 C36 112.5(6) . . ? O44 C48 H48A 109.1 . . ? C36 C48 H48A 109.1 . . ? O44 C48 H48B 109.1 . . ? C36 C48 H48B 109.1 . . ? H48A C48 H48B 107.8 . . ? 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 C5 O1 C1 C7 -175.4(6) . . . . ? C5 O1 C1 C2 61.5(7) . . . . ? C6 O2 C2 C1 142.8(6) . . . . ? C6 O2 C2 C3 -97.8(6) . . . . ? O1 C1 C2 O2 67.4(7) . . . . ? C7 C1 C2 O2 -54.0(7) . . . . ? O1 C1 C2 C3 -50.4(8) . . . . ? C7 C1 C2 C3 -171.8(6) . . . . ? O2 C2 C3 C4 -71.8(8) . . . . ? C1 C2 C3 C4 45.4(9) . . . . ? C2 C3 C4 C5 -52.5(10) . . . . ? C1 O1 C5 C4 -64.7(8) . . . . ? C3 C4 C5 O1 59.2(9) . . . . ? C2 O2 C6 O3 5.5(12) . . . . ? C2 O2 C6 C28 -176.9(7) . . . . ? C8 O4 C7 C1 -177.5(8) . . . . ? O1 C1 C7 O4 68.9(9) . . . . ? C2 C1 C7 O4 -168.2(7) . . . . ? C7 O4 C8 C46 -102.2(9) . . . . ? C25 O21 C21 C27 -170.9(6) . . . . ? C25 O21 C21 C22 60.8(7) . . . . ? C26 O22 C22 C21 158.0(6) . . . . ? C26 O22 C22 C23 -81.9(7) . . . . ? O21 C21 C22 O22 66.5(6) . . . . ? C27 C21 C22 O22 -57.5(8) . . . . ? O21 C21 C22 C23 -51.4(7) . . . . ? C27 C21 C22 C23 -175.5(7) . . . . ? O22 C22 C23 C24 -68.1(7) . . . . ? C21 C22 C23 C24 47.7(8) . . . . ? C22 C23 C24 C25 -51.2(8) . . . . ? C21 O21 C25 C24 -59.9(8) . . . . ? C23 C24 C25 O21 56.6(8) . . . . ? C22 O22 C26 O23 -0.8(11) . . . . ? C22 O22 C26 C38 174.9(6) . . . . ? C28 O24 C27 C21 -178.7(8) . . . . ? O21 C21 C27 O24 60.0(9) . . . . ? C22 C21 C27 O24 -173.1(7) . . . . ? C27 O24 C28 C6 -85.5(9) . . . . ? O3 C6 C28 O24 4.3(15) . . . . ? O2 C6 C28 O24 -173.1(6) . . . . ? C35 O31 C31 C37 -176.1(5) . . . . ? C35 O31 C31 C32 59.5(6) . . . . ? C36 O32 C32 C33 -97.3(6) . . . . ? C36 O32 C32 C31 143.2(5) . . . . ? O31 C31 C32 O32 67.8(6) . . . . ? C37 C31 C32 O32 -53.6(6) . . . . ? O31 C31 C32 C33 -51.5(7) . . . . ? C37 C31 C32 C33 -172.9(5) . . . . ? O32 C32 C33 C34 -68.0(7) . . . . ? C31 C32 C33 C34 49.0(8) . . . . ? C32 C33 C34 C35 -53.1(8) . . . . ? C31 O31 C35 C34 -66.2(7) . . . . ? C33 C34 C35 O31 62.7(8) . . . . ? C32 O32 C36 O33 -4.4(9) . . . . ? C32 O32 C36 C48 173.4(6) . . . . ? C38 O34 C37 C31 -178.4(6) . . . . ? O31 C31 C37 O34 64.3(6) . . . . ? C32 C31 C37 O34 -171.3(5) . . . . ? C37 O34 C38 C26 -89.8(8) . . . . ? O23 C26 C38 O34 10.5(13) . . . . ? O22 C26 C38 O34 -165.0(6) . . . . ? C45 O41 C41 C42 61.9(7) . . . . ? C45 O41 C41 C47 -174.8(5) . . . . ? C46 O42 C42 C41 161.3(6) . . . . ? C46 O42 C42 C43 -79.7(8) . . . . ? O41 C41 C42 O42 61.6(7) . . . . ? C47 C41 C42 O42 -58.3(7) . . . . ? O41 C41 C42 C43 -57.9(7) . . . . ? C47 C41 C42 C43 -177.7(5) . . . . ? O42 C42 C43 C44 -69.7(7) . . . . ? C41 C42 C43 C44 50.3(7) . . . . ? C42 C43 C44 C45 -49.7(9) . . . . ? C43 C44 C45 O41 53.2(9) . . . . ? C41 O41 C45 C44 -60.8(8) . . . . ? C42 O42 C46 O43 1.3(12) . . . . ? C42 O42 C46 C8 178.6(6) . . . . ? O4 C8 C46 O43 4.6(14) . . . . ? O4 C8 C46 O42 -172.8(7) . . . . ? C48 O44 C47 C41 -171.7(5) . . . . ? O41 C41 C47 O44 71.9(6) . . . . ? C42 C41 C47 O44 -164.3(5) . . . . ? C47 O44 C48 C36 -87.0(8) . . . . ? O33 C36 C48 O44 -4.7(12) . . . . ? O32 C36 C48 O44 177.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.299 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.071 data_trans-TETRAMER(35) _database_code_depnum_ccdc_archive 'CCDC 266198' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H48 O16' _chemical_formula_weight 688.70 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 0.0000 '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 0.0000 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.443(17) _cell_length_b 7.313(5) _cell_length_c 15.038(16) _cell_angle_alpha 90.00 _cell_angle_beta 122.19(5) _cell_angle_gamma 90.00 _cell_volume 1716(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colurless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Enraf-Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2090 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2090 _reflns_number_gt 1911 _reflns_threshold_expression >4sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et atl. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek 2003)' _computing_publication_material ? _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^)+(0.0441P)^2^+0.3777P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(2) _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(10) _refine_ls_number_reflns 2090 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.73088(12) -0.5998(3) 0.32812(14) 0.0557(5) Uani 1 1 d . . . O2 O 0.74021(9) -0.2816(2) 0.14906(12) 0.0421(4) Uani 1 1 d . . . O3 O 0.62965(11) -0.0860(3) 0.06726(17) 0.0680(6) Uani 1 1 d . . . O4 O 0.77091(9) -0.2257(3) 0.39084(12) 0.0501(5) Uani 1 1 d . . . O21 O 1.10745(9) 0.3033(2) 0.80816(13) 0.0447(4) Uani 1 1 d . . . O22 O 0.92643(9) 0.0249(2) 0.61795(11) 0.0430(4) Uani 1 1 d . . . O23 O 0.88796(12) 0.0652(4) 0.44978(13) 0.0663(6) Uani 1 1 d . . . O24 O 1.15900(9) -0.0747(2) 0.88625(11) 0.0439(4) Uani 1 1 d . . . C1 C 0.76681(14) -0.4792(4) 0.28734(17) 0.0408(5) Uani 1 1 d . . . H1 H 0.8029 -0.5507 0.2704 0.049 Uiso 1 1 calc R . . C2 C 0.69545(13) -0.3902(4) 0.18692(17) 0.0404(5) Uani 1 1 d . . . H2 H 0.6613 -0.3101 0.2029 0.049 Uiso 1 1 calc R . . C3 C 0.63818(18) -0.5317(4) 0.1060(2) 0.0562(7) Uani 1 1 d . . . H3A H 0.6696 -0.5949 0.0801 0.067 Uiso 1 1 calc R . . H3B H 0.5891 -0.4720 0.0471 0.067 Uiso 1 1 calc R . . C4 C 0.60788(18) -0.6689(4) 0.1559(2) 0.0629(8) Uani 1 1 d . . . H4A H 0.5687 -0.6095 0.1713 0.075 Uiso 1 1 calc R . . H4B H 0.5775 -0.7683 0.1072 0.075 Uiso 1 1 calc R . . C5 C 0.6833(2) -0.7436(4) 0.2557(2) 0.0630(8) Uani 1 1 d . . . H5A H 0.6633 -0.8283 0.2877 0.076 Uiso 1 1 calc R . . H5B H 0.7204 -0.8101 0.2394 0.076 Uiso 1 1 calc R . . C6 C 0.70087(14) -0.1321(4) 0.09329(17) 0.0420(5) Uani 1 1 d . . . C7 C 0.75401(14) -0.0255(4) 0.06241(18) 0.0474(6) Uani 1 1 d . . . H7A H 0.7286 -0.0395 -0.0127 0.057 Uiso 1 1 calc R . . H7B H 0.7507 0.1031 0.0758 0.057 Uiso 1 1 calc R . . C8 C 0.82265(13) -0.3449(4) 0.37242(18) 0.0450(6) Uani 1 1 d . . . H8A H 0.8624 -0.4101 0.4365 0.054 Uiso 1 1 calc R . . H8B H 0.8557 -0.2741 0.3516 0.054 Uiso 1 1 calc R . . C21 C 1.05300(12) 0.1466(3) 0.76717(16) 0.0349(5) Uani 1 1 d . . . H21 H 1.0261 0.1254 0.8076 0.042 Uiso 1 1 calc R . . C22 C 0.98331(12) 0.1827(3) 0.65226(16) 0.0366(5) Uani 1 1 d . . . H22 H 1.0089 0.1943 0.6098 0.044 Uiso 1 1 calc R . . C23 C 0.93277(13) 0.3534(4) 0.64184(19) 0.0462(6) Uani 1 1 d . . . H23A H 0.9004 0.3338 0.6750 0.055 Uiso 1 1 calc R . . H23B H 0.8926 0.3802 0.5681 0.055 Uiso 1 1 calc R . . C24 C 0.99371(15) 0.5131(4) 0.6938(2) 0.0542(7) Uani 1 1 d . . . H24A H 1.0198 0.5437 0.6543 0.065 Uiso 1 1 calc R . . H24B H 0.9621 0.6191 0.6938 0.065 Uiso 1 1 calc R . . C25 C 1.06247(16) 0.4656(4) 0.8051(2) 0.0554(7) Uani 1 1 d . . . H25A H 1.1026 0.5664 0.8360 0.066 Uiso 1 1 calc R . . H25B H 1.0367 0.4468 0.8463 0.066 Uiso 1 1 calc R . . C26 C 0.87923(13) -0.0100(4) 0.51425(16) 0.0415(6) Uani 1 1 d . . . C27 C 0.81351(14) -0.1539(4) 0.49315(19) 0.0505(7) Uani 1 1 d . . . H27A H 0.8416 -0.2532 0.5428 0.061 Uiso 1 1 calc R . . H27B H 0.7714 -0.1015 0.5056 0.061 Uiso 1 1 calc R . . C28 C 1.10823(14) -0.0152(3) 0.77973(17) 0.0419(6) Uani 1 1 d . . . H28A H 1.0719 -0.1151 0.7365 0.050 Uiso 1 1 calc R . . H28B H 1.1456 0.0175 0.7552 0.050 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 0.0738(11) 0.0580(12) 0.0518(10) -0.0031(9) 0.0445(9) -0.0112(10) O2 0.0376(7) 0.0528(10) 0.0371(8) 0.0045(8) 0.0207(6) 0.0013(7) O3 0.0463(10) 0.0750(15) 0.0777(14) 0.0158(12) 0.0296(9) 0.0163(10) O4 0.0330(7) 0.0719(12) 0.0350(8) -0.0186(9) 0.0110(6) -0.0019(8) O21 0.0314(7) 0.0421(9) 0.0418(9) -0.0040(7) 0.0069(7) -0.0025(7) O22 0.0382(8) 0.0559(11) 0.0280(7) -0.0047(7) 0.0130(6) -0.0147(8) O23 0.0706(11) 0.0912(16) 0.0349(9) -0.0050(10) 0.0267(8) -0.0239(12) O24 0.0415(8) 0.0533(10) 0.0329(8) 0.0082(8) 0.0172(6) 0.0065(8) C1 0.0444(11) 0.0466(14) 0.0398(11) -0.0009(11) 0.0280(10) -0.0002(11) C2 0.0381(10) 0.0533(14) 0.0340(11) -0.0055(10) 0.0219(9) -0.0029(10) C3 0.0540(14) 0.0679(18) 0.0455(14) -0.0145(13) 0.0258(11) -0.0132(14) C4 0.0632(16) 0.065(2) 0.0721(19) -0.0233(16) 0.0438(15) -0.0229(15) C5 0.0818(19) 0.0538(17) 0.0749(19) -0.0103(16) 0.0561(17) -0.0170(16) C6 0.0370(11) 0.0488(14) 0.0303(10) -0.0035(10) 0.0113(8) 0.0015(10) C7 0.0453(11) 0.0521(15) 0.0325(11) 0.0046(11) 0.0125(9) -0.0006(11) C8 0.0360(10) 0.0617(16) 0.0346(11) 0.0003(11) 0.0169(9) 0.0014(11) C21 0.0289(9) 0.0416(12) 0.0280(10) -0.0017(9) 0.0109(8) -0.0022(9) C22 0.0295(9) 0.0465(13) 0.0288(10) 0.0002(10) 0.0121(8) -0.0066(10) C23 0.0302(10) 0.0549(15) 0.0410(12) 0.0060(12) 0.0106(9) 0.0018(11) C24 0.0397(12) 0.0487(15) 0.0584(15) 0.0067(13) 0.0154(11) 0.0062(12) C25 0.0473(12) 0.0452(15) 0.0505(14) -0.0097(12) 0.0105(11) 0.0003(12) C26 0.0332(10) 0.0589(16) 0.0274(10) -0.0032(10) 0.0128(8) -0.0020(10) C27 0.0385(11) 0.0744(19) 0.0364(12) -0.0183(12) 0.0183(10) -0.0151(12) C28 0.0404(11) 0.0472(15) 0.0306(11) -0.0012(10) 0.0139(9) 0.0014(10) _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 C1 1.423(3) . ? O1 C5 1.430(4) . ? O2 C6 1.333(3) . ? O2 C2 1.462(3) . ? O3 C6 1.202(3) . ? O4 C27 1.404(3) . ? O4 C8 1.425(3) . ? O21 C21 1.429(3) . ? O21 C25 1.435(3) . ? O22 C26 1.345(3) . ? O22 C22 1.456(3) . ? O23 C26 1.198(3) . ? O24 C7 1.407(3) 2_756 ? O24 C28 1.426(3) . ? C1 C8 1.503(3) . ? C1 C2 1.523(3) . ? C1 H1 0.9800 . ? C2 C3 1.516(4) . ? C2 H2 0.9800 . ? C3 C4 1.526(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.503(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.506(4) . ? C7 O24 1.407(3) 2_756 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C21 C28 1.506(3) . ? C21 C22 1.530(3) . ? C21 H21 0.9800 . ? C22 C23 1.515(4) . ? C22 H22 0.9800 . ? C23 C24 1.518(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.506(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.506(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? 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 C1 O1 C5 111.4(2) . . ? C6 O2 C2 117.38(18) . . ? C27 O4 C8 113.58(18) . . ? C21 O21 C25 112.85(17) . . ? C26 O22 C22 117.40(18) . . ? C7 O24 C28 114.36(18) 2_756 . ? O1 C1 C8 107.7(2) . . ? O1 C1 C2 109.71(18) . . ? C8 C1 C2 113.8(2) . . ? O1 C1 H1 108.5 . . ? C8 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? O2 C2 C3 110.8(2) . . ? O2 C2 C1 104.45(17) . . ? C3 C2 C1 111.6(2) . . ? O2 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C2 C3 C4 109.6(2) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 110.0(2) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? O1 C5 C4 111.0(3) . . ? O1 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? O1 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? O3 C6 O2 124.7(2) . . ? O3 C6 C7 122.2(2) . . ? O2 C6 C7 113.14(19) . . ? O24 C7 C6 115.9(2) 2_756 . ? O24 C7 H7A 108.3 2_756 . ? C6 C7 H7A 108.3 . . ? O24 C7 H7B 108.3 2_756 . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O4 C8 C1 109.84(18) . . ? O4 C8 H8A 109.7 . . ? C1 C8 H8A 109.7 . . ? O4 C8 H8B 109.7 . . ? C1 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O21 C21 C28 107.64(17) . . ? O21 C21 C22 108.86(18) . . ? C28 C21 C22 112.47(19) . . ? O21 C21 H21 109.3 . . ? C28 C21 H21 109.3 . . ? C22 C21 H21 109.3 . . ? O22 C22 C23 109.20(17) . . ? O22 C22 C21 106.06(18) . . ? C23 C22 C21 111.06(19) . . ? O22 C22 H22 110.1 . . ? C23 C22 H22 110.1 . . ? C21 C22 H22 110.1 . . ? C22 C23 C24 109.57(18) . . ? C22 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? C22 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? C25 C24 C23 110.4(2) . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? O21 C25 C24 110.9(2) . . ? O21 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? O21 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? O23 C26 O22 124.6(2) . . ? O23 C26 C27 126.2(2) . . ? O22 C26 C27 109.15(19) . . ? O4 C27 C26 114.2(2) . . ? O4 C27 H27A 108.7 . . ? C26 C27 H27A 108.7 . . ? O4 C27 H27B 108.7 . . ? C26 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? O24 C28 C21 112.09(19) . . ? O24 C28 H28A 109.2 . . ? C21 C28 H28A 109.2 . . ? O24 C28 H28B 109.2 . . ? C21 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? 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 C5 O1 C1 C8 -174.3(2) . . . . ? C5 O1 C1 C2 61.4(3) . . . . ? C6 O2 C2 C3 88.5(3) . . . . ? C6 O2 C2 C1 -151.13(19) . . . . ? O1 C1 C2 O2 -175.98(18) . . . . ? C8 C1 C2 O2 63.4(2) . . . . ? O1 C1 C2 C3 -56.2(3) . . . . ? C8 C1 C2 C3 -176.85(19) . . . . ? O2 C2 C3 C4 167.6(2) . . . . ? C1 C2 C3 C4 51.7(3) . . . . ? C2 C3 C4 C5 -51.9(3) . . . . ? C1 O1 C5 C4 -63.3(3) . . . . ? C3 C4 C5 O1 57.7(3) . . . . ? C2 O2 C6 O3 -4.2(3) . . . . ? C2 O2 C6 C7 177.34(19) . . . . ? O3 C6 C7 O24 168.7(2) . . . 2_756 ? O2 C6 C7 O24 -12.8(3) . . . 2_756 ? C27 O4 C8 C1 153.4(2) . . . . ? O1 C1 C8 O4 -69.0(2) . . . . ? C2 C1 C8 O4 52.8(3) . . . . ? C25 O21 C21 C28 -177.2(2) . . . . ? C25 O21 C21 C22 60.6(2) . . . . ? C26 O22 C22 C23 83.3(2) . . . . ? C26 O22 C22 C21 -156.94(18) . . . . ? O21 C21 C22 O22 -175.59(16) . . . . ? C28 C21 C22 O22 65.2(2) . . . . ? O21 C21 C22 C23 -57.1(2) . . . . ? C28 C21 C22 C23 -176.27(19) . . . . ? O22 C22 C23 C24 170.72(19) . . . . ? C21 C22 C23 C24 54.1(3) . . . . ? C22 C23 C24 C25 -53.2(3) . . . . ? C21 O21 C25 C24 -61.2(3) . . . . ? C23 C24 C25 O21 56.1(3) . . . . ? C22 O22 C26 O23 9.4(4) . . . . ? C22 O22 C26 C27 -169.38(19) . . . . ? C8 O4 C27 C26 73.2(3) . . . . ? O23 C26 C27 O4 12.3(4) . . . . ? O22 C26 C27 O4 -168.9(2) . . . . ? C7 O24 C28 C21 -104.4(2) 2_756 . . . ? O21 C21 C28 O24 74.0(2) . . . . ? C22 C21 C28 O24 -166.11(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.167 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032 # Attachment 'Macrodiolide_3.cif' data_Macrodiolide_3_(revised) _database_code_depnum_ccdc_archive 'CCDC 776407' #TrackingRef 'Macrodiolide_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O8' _chemical_formula_weight 344.35 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.546(7) _cell_length_b 4.490(1) _cell_length_c 14.124(7) _cell_angle_alpha 90.00 _cell_angle_beta 125.50(3) _cell_angle_gamma 90.00 _cell_volume 854.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1113 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.94 _reflns_number_total 1113 _reflns_number_gt 1020 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1060P)^2^+0.0205P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.30(4) _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 -10(10) _refine_ls_number_reflns 1113 _refine_ls_number_parameters 110 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_restrained_S_all 1.260 _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 1.06502(14) 0.3846(6) 0.76216(15) 0.0504(7) Uani 1 1 d . . . O2 O 0.87762(12) 0.4382(5) 0.81953(14) 0.0384(6) Uani 1 1 d . . . O3 O 0.75179(17) 0.1095(7) 0.72155(19) 0.0632(8) Uani 1 1 d . . . O4 O 0.83819(13) 0.5276(6) 0.97931(14) 0.0433(6) Uani 1 1 d . . . C1 C 1.02318(17) 0.4532(7) 0.8238(2) 0.0368(7) Uani 1 1 d . . . H1 H 1.0239 0.6698 0.8329 0.044 Uiso 1 1 calc R . . C2 C 0.91533(17) 0.3440(7) 0.75374(19) 0.0358(7) Uani 1 1 d . . . H2 H 0.9140 0.1261 0.7489 0.043 Uiso 1 1 calc R . . C3 C 0.8546(2) 0.4751(8) 0.6318(2) 0.0441(8) Uani 1 1 d . . . H3A H 0.8458 0.6872 0.6359 0.053 Uiso 1 1 calc R . . H3B H 0.7895 0.3830 0.5862 0.053 Uiso 1 1 calc R . . C4 C 0.9071(2) 0.4223(12) 0.5731(2) 0.0574(10) Uani 1 1 d . . . H4A H 0.9059 0.2116 0.5571 0.069 Uiso 1 1 calc R . . H4B H 0.8726 0.5286 0.4997 0.069 Uiso 1 1 calc R . . C5 C 1.0139(2) 0.5295(14) 0.6512(3) 0.0654(12) Uani 1 1 d . . . H5A H 1.0474 0.4871 0.6148 0.079 Uiso 1 1 calc R . . H5B H 1.0149 0.7432 0.6617 0.079 Uiso 1 1 calc R . . C6 C 0.79578(19) 0.2963(8) 0.7956(2) 0.0423(7) Uani 1 1 d . . . C7 C 0.76315(18) 0.4024(10) 0.8705(2) 0.0477(8) Uani 1 1 d . . . H7A H 0.7112 0.5499 0.8268 0.057 Uiso 1 1 calc R . . H7B H 0.7342 0.2349 0.8843 0.057 Uiso 1 1 calc R . . C8 C 0.91013(19) 0.3125(7) 1.0570(2) 0.0389(7) Uani 1 1 d . . . H8A H 0.9492 0.2495 1.0295 0.047 Uiso 1 1 calc R . . H8B H 0.8772 0.1390 1.0609 0.047 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 0.0314(10) 0.0873(19) 0.0320(10) 0.0111(12) 0.0180(8) 0.0092(12) O2 0.0274(9) 0.0519(12) 0.0326(9) -0.0092(9) 0.0155(7) -0.0033(9) O3 0.0449(12) 0.092(2) 0.0509(12) -0.0287(14) 0.0270(10) -0.0304(14) O4 0.0301(10) 0.0592(13) 0.0288(9) -0.0052(9) 0.0104(8) 0.0076(9) C1 0.0259(11) 0.0489(16) 0.0282(11) 0.0027(12) 0.0114(9) 0.0011(12) C2 0.0268(11) 0.0476(16) 0.0276(12) -0.0046(11) 0.0127(10) 0.0015(11) C3 0.0278(12) 0.062(2) 0.0283(11) 0.0006(13) 0.0079(10) 0.0023(12) C4 0.0433(15) 0.090(3) 0.0307(12) 0.0097(17) 0.0167(12) 0.013(2) C5 0.0398(15) 0.118(4) 0.0361(15) 0.022(2) 0.0205(13) 0.003(2) C6 0.0232(11) 0.0651(19) 0.0288(12) -0.0036(13) 0.0095(10) -0.0010(13) C7 0.0227(12) 0.080(2) 0.0298(12) -0.0070(15) 0.0090(10) 0.0011(15) C8 0.0284(12) 0.0499(16) 0.0313(12) -0.0014(12) 0.0133(10) 0.0015(12) _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 C1 1.425(3) . ? O1 C5 1.433(4) . ? O2 C6 1.350(3) . ? O2 C2 1.451(3) . ? O3 C6 1.201(4) . ? O4 C7 1.416(3) . ? O4 C8 1.427(3) . ? C1 C8 1.515(4) 2_757 ? C1 C2 1.534(4) . ? C1 H1 0.9800 . ? C2 C3 1.520(4) . ? C2 H2 0.9800 . ? C3 C4 1.529(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.518(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.517(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C1 1.515(4) 2_757 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C1 O1 C5 112.4(2) . . ? C6 O2 C2 116.4(2) . . ? C7 O4 C8 112.3(2) . . ? O1 C1 C8 106.9(2) . 2_757 ? O1 C1 C2 109.4(2) . . ? C8 C1 C2 114.0(2) 2_757 . ? O1 C1 H1 108.8 . . ? C8 C1 H1 108.8 2_757 . ? C2 C1 H1 108.8 . . ? O2 C2 C3 111.4(2) . . ? O2 C2 C1 105.41(19) . . ? C3 C2 C1 111.3(2) . . ? O2 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? C2 C3 C4 110.1(2) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.1(3) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O1 C5 C4 110.5(3) . . ? O1 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? O1 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? O3 C6 O2 124.1(3) . . ? O3 C6 C7 123.0(3) . . ? O2 C6 C7 112.9(3) . . ? O4 C7 C6 116.0(2) . . ? O4 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? O4 C7 H7B 108.3 . . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O4 C8 C1 108.4(2) . 2_757 ? O4 C8 H8A 110.0 . . ? C1 C8 H8A 110.0 2_757 . ? O4 C8 H8B 110.0 . . ? C1 C8 H8B 110.0 2_757 . ? H8A C8 H8B 108.4 . . ? 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 C5 O1 C1 C8 -174.4(3) . . . 2_757 ? C5 O1 C1 C2 61.6(4) . . . . ? C6 O2 C2 C3 78.2(3) . . . . ? C6 O2 C2 C1 -161.0(2) . . . . ? O1 C1 C2 O2 -176.8(2) . . . . ? C8 C1 C2 O2 63.5(3) 2_757 . . . ? O1 C1 C2 C3 -55.9(3) . . . . ? C8 C1 C2 C3 -175.5(3) 2_757 . . . ? O2 C2 C3 C4 169.2(3) . . . . ? C1 C2 C3 C4 51.8(4) . . . . ? C2 C3 C4 C5 -51.9(5) . . . . ? C1 O1 C5 C4 -63.0(5) . . . . ? C3 C4 C5 O1 56.7(5) . . . . ? C2 O2 C6 O3 -2.9(4) . . . . ? C2 O2 C6 C7 178.4(2) . . . . ? C8 O4 C7 C6 -67.4(4) . . . . ? O3 C6 C7 O4 156.2(3) . . . . ? O2 C6 C7 O4 -25.1(5) . . . . ? C7 O4 C8 C1 -170.7(2) . . . 2_757 ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.387 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.110 # Attachment 'Macrotetraolide_2.cif' data_MACROTETRAOLIDE_2_(REVISED) _database_code_depnum_ccdc_archive 'CCDC 776408' #TrackingRef 'Macrotetraolide_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H48 O16' _chemical_formula_sum 'C32 H48 O16' _chemical_formula_weight 688.70 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.052(2) _cell_length_b 27.546(6) _cell_length_c 9.808(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.28(2) _cell_angle_gamma 90.00 _cell_volume 2211.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4388 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4388 _reflns_number_gt 2546 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et atl., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L. Spek, 2003)' _computing_publication_material ? _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^)+(0.1675P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.066(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4388 _refine_ls_number_parameters 434 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2218 _refine_ls_wR_factor_gt 0.2056 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5085(5) 0.36441(13) 0.1066(4) 0.0735(11) Uani 1 1 d . . . O2 O 0.4094(5) 0.39913(15) 0.3327(4) 0.0689(10) Uani 1 1 d . . . O3 O 0.4827(8) 0.4148(4) 0.5803(7) 0.170(4) Uani 1 1 d . . . O4 O 0.5142(8) 0.26618(17) 0.1889(10) 0.135(2) Uani 1 1 d . . . O21 O -0.0391(5) 0.43519(15) 0.6677(4) 0.0713(10) Uani 1 1 d . . . O22 O -0.0001(5) 0.33470(13) 0.7506(4) 0.0705(10) Uani 1 1 d . . . O23 O 0.1225(6) 0.27660(18) 0.9237(6) 0.1144(19) Uani 1 1 d . . . O24 O 0.1594(7) 0.43238(16) 0.5216(6) 0.1006(15) Uani 1 1 d . . . O31 O -0.2306(4) 0.11944(12) 0.7582(4) 0.0618(9) Uani 1 1 d . . . O32 O 0.0274(4) 0.08231(14) 0.6827(4) 0.0654(10) Uani 1 1 d . . . O33 O 0.2990(5) 0.0687(2) 0.7610(5) 0.1018(16) Uani 1 1 d . . . O34 O -0.1326(6) 0.21525(14) 0.7762(7) 0.0970(15) Uani 1 1 d . . . O41 O 0.3508(4) 0.04681(13) 0.2351(4) 0.0664(10) Uani 1 1 d . . . O42 O 0.4681(4) 0.14463(13) 0.2792(4) 0.0670(10) Uani 1 1 d . . . O43 O 0.6768(8) 0.1946(3) 0.3816(7) 0.150(3) Uani 1 1 d . . . O44 O 0.2448(5) 0.04582(15) 0.4672(5) 0.0822(12) Uani 1 1 d . . . C1 C 0.5766(7) 0.3485(2) 0.2538(7) 0.0726(15) Uani 1 1 d . . . H1 H 0.6896 0.3387 0.2801 0.087 Uiso 1 1 calc R . . C2 C 0.5788(8) 0.3889(3) 0.3624(6) 0.0796(18) Uani 1 1 d . . . H2 H 0.6405 0.3784 0.4671 0.096 Uiso 1 1 calc R . . C3 C 0.6535(8) 0.4370(3) 0.3328(7) 0.0858(18) Uani 1 1 d . . . H3A H 0.6280 0.4639 0.3828 0.103 Uiso 1 1 calc R . . H3B H 0.7714 0.4341 0.3736 0.103 Uiso 1 1 calc R . . C4 C 0.5848(10) 0.4466(3) 0.1671(8) 0.096(2) Uani 1 1 d . . . H4A H 0.4709 0.4557 0.1315 0.116 Uiso 1 1 calc R . . H4B H 0.6424 0.4738 0.1498 0.116 Uiso 1 1 calc R . . C5 C 0.5961(8) 0.4048(3) 0.0780(7) 0.0803(17) Uani 1 1 d . . . H5A H 0.5474 0.4128 -0.0285 0.096 Uiso 1 1 calc R . . H5B H 0.7095 0.3961 0.1079 0.096 Uiso 1 1 calc R . . C6 C 0.3786(9) 0.4095(2) 0.4551(8) 0.0832(18) Uani 1 1 d . . . C7 C 0.4827(9) 0.3043(2) 0.2644(9) 0.0882(19) Uani 1 1 d . . . H7A H 0.5160 0.2956 0.3693 0.106 Uiso 1 1 calc R . . H7B H 0.3665 0.3113 0.2197 0.106 Uiso 1 1 calc R . . C8 C 0.4329(10) 0.2247(2) 0.1828(10) 0.104(2) Uani 1 1 d . . . H8A H 0.3925 0.2113 0.0818 0.125 Uiso 1 1 calc R . . H8B H 0.3394 0.2318 0.2032 0.125 Uiso 1 1 calc R . . C21 C 0.1121(7) 0.41057(18) 0.7318(6) 0.0611(13) Uani 1 1 d . . . H21 H 0.1950 0.4347 0.7888 0.073 Uiso 1 1 calc R . . C22 C 0.1193(6) 0.37130(18) 0.8421(6) 0.0568(12) Uani 1 1 d . . . H22 H 0.2291 0.3572 0.8902 0.068 Uiso 1 1 calc R . . C23 C 0.0665(8) 0.3905(2) 0.9613(6) 0.0785(17) Uani 1 1 d . . . H23A H 0.0500 0.3634 1.0166 0.094 Uiso 1 1 calc R . . H23B H 0.1520 0.4109 1.0323 0.094 Uiso 1 1 calc R . . C24 C -0.0853(9) 0.4185(3) 0.8903(7) 0.090(2) Uani 1 1 d . . . H24A H -0.1076 0.4339 0.9686 0.108 Uiso 1 1 calc R . . H24B H -0.1747 0.3965 0.8357 0.108 Uiso 1 1 calc R . . C25 C -0.0799(9) 0.4594(2) 0.7768(8) 0.0854(18) Uani 1 1 d . . . H25A H -0.1853 0.4753 0.7274 0.102 Uiso 1 1 calc R . . H25B H 0.0018 0.4837 0.8308 0.102 Uiso 1 1 calc R . . C26 C 0.0147(8) 0.2893(2) 0.8046(7) 0.0753(16) Uani 1 1 d . . . C27 C 0.1501(11) 0.3941(2) 0.6056(9) 0.099(2) Uani 1 1 d . . . H27A H 0.2534 0.3767 0.6463 0.119 Uiso 1 1 calc R . . H27B H 0.0659 0.3718 0.5417 0.119 Uiso 1 1 calc R . . C28 C 0.1914(12) 0.4157(4) 0.3942(10) 0.123(3) Uani 1 1 d . . . H28A H 0.1522 0.4394 0.3133 0.148 Uiso 1 1 calc R . . H28B H 0.1365 0.3851 0.3557 0.148 Uiso 1 1 calc R . . C31 C -0.0615(6) 0.13292(19) 0.8318(6) 0.0592(13) Uani 1 1 d . . . H31 H -0.0370 0.1423 0.9356 0.071 Uiso 1 1 calc R . . C32 C 0.0531(6) 0.09083(19) 0.8378(6) 0.0644(14) Uani 1 1 d . . . H32 H 0.1671 0.0999 0.8996 0.077 Uiso 1 1 calc R . . C33 C 0.0097(8) 0.0449(3) 0.9013(8) 0.090(2) Uani 1 1 d . . . H33A H 0.0689 0.0175 0.8870 0.108 Uiso 1 1 calc R . . H33B H 0.0437 0.0489 1.0088 0.108 Uiso 1 1 calc R . . C34 C -0.1705(9) 0.0344(2) 0.8260(8) 0.089(2) Uani 1 1 d . . . H34A H -0.1967 0.0076 0.8760 0.106 Uiso 1 1 calc R . . H34B H -0.2035 0.0257 0.7211 0.106 Uiso 1 1 calc R . . C35 C -0.2587(8) 0.0803(3) 0.8372(8) 0.0843(17) Uani 1 1 d . . . H35A H -0.3751 0.0739 0.7964 0.101 Uiso 1 1 calc R . . H35B H -0.2214 0.0891 0.9425 0.101 Uiso 1 1 calc R . . C36 C 0.1640(7) 0.06986(19) 0.6623(7) 0.0650(14) Uani 1 1 d . . . C37 C -0.0374(7) 0.1762(2) 0.7531(7) 0.0708(15) Uani 1 1 d . . . H37A H 0.0773 0.1850 0.7948 0.085 Uiso 1 1 calc R . . H37B H -0.0749 0.1696 0.6464 0.085 Uiso 1 1 calc R . . C38 C -0.1257(10) 0.2602(2) 0.7002(10) 0.101(2) Uani 1 1 d . . . H38A H -0.2264 0.2783 0.6721 0.121 Uiso 1 1 calc R . . H38B H -0.1125 0.2529 0.6093 0.121 Uiso 1 1 calc R . . C41 C 0.4402(6) 0.06704(19) 0.3760(6) 0.0602(13) Uani 1 1 d . . . H41 H 0.5040 0.0412 0.4447 0.072 Uiso 1 1 calc R . . C42 C 0.5564(6) 0.10588(19) 0.3737(6) 0.0609(13) Uani 1 1 d . . . H42 H 0.6208 0.1179 0.4762 0.073 Uiso 1 1 calc R . . C43 C 0.6713(8) 0.0831(3) 0.3112(9) 0.100(2) Uani 1 1 d . . . H43A H 0.7452 0.0606 0.3849 0.121 Uiso 1 1 calc R . . H43B H 0.7365 0.1086 0.2953 0.121 Uiso 1 1 calc R . . C44 C 0.5744(9) 0.0558(3) 0.1598(8) 0.0846(19) Uani 1 1 d . . . H44A H 0.5162 0.0789 0.0803 0.102 Uiso 1 1 calc R . . H44B H 0.6493 0.0378 0.1318 0.102 Uiso 1 1 calc R . . C45 C 0.4585(9) 0.0225(3) 0.1782(8) 0.092(2) Uani 1 1 d . . . H45A H 0.5186 -0.0031 0.2478 0.111 Uiso 1 1 calc R . . H45B H 0.3919 0.0075 0.0818 0.111 Uiso 1 1 calc R . . C46 C 0.5393(8) 0.1869(3) 0.2952(8) 0.088(2) Uani 1 1 d . . . C47 C 0.3143(7) 0.0864(2) 0.4309(7) 0.0721(15) Uani 1 1 d . . . H47A H 0.3677 0.1070 0.5187 0.086 Uiso 1 1 calc R . . H47B H 0.2306 0.1053 0.3521 0.086 Uiso 1 1 calc R . . C48 C 0.1116(7) 0.0566(3) 0.4976(7) 0.084(2) Uani 1 1 d . . . H48A H 0.0393 0.0287 0.4726 0.101 Uiso 1 1 calc R . . H48B H 0.0513 0.0835 0.4345 0.101 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 0.104(3) 0.053(2) 0.078(2) 0.0059(18) 0.052(2) -0.006(2) O2 0.084(3) 0.081(3) 0.0543(19) -0.0043(18) 0.0406(17) 0.004(2) O3 0.136(4) 0.308(11) 0.091(4) -0.098(5) 0.071(3) -0.082(6) O4 0.161(5) 0.051(3) 0.255(8) 0.006(4) 0.148(5) 0.009(3) O21 0.096(3) 0.072(2) 0.0547(19) 0.0079(18) 0.0406(18) 0.008(2) O22 0.092(3) 0.048(2) 0.069(2) -0.0066(18) 0.0316(19) -0.0088(18) O23 0.120(4) 0.067(3) 0.106(3) 0.016(3) 0.000(3) 0.020(3) O24 0.177(5) 0.056(2) 0.116(3) 0.005(2) 0.108(3) 0.017(3) O31 0.065(2) 0.058(2) 0.072(2) 0.0128(17) 0.0382(17) 0.0049(16) O32 0.062(2) 0.081(3) 0.063(2) -0.0039(18) 0.0361(16) 0.0155(18) O33 0.057(2) 0.143(4) 0.099(3) 0.018(3) 0.027(2) 0.011(3) O34 0.123(3) 0.041(2) 0.152(4) 0.014(2) 0.083(3) 0.003(2) O41 0.079(2) 0.0465(19) 0.081(2) -0.0174(18) 0.0409(19) -0.0013(17) O42 0.0568(19) 0.059(2) 0.072(2) 0.0077(18) 0.0157(16) -0.0183(17) O43 0.142(5) 0.178(7) 0.112(4) 0.011(4) 0.036(4) -0.097(5) O44 0.099(3) 0.069(2) 0.119(3) 0.002(2) 0.085(3) 0.014(2) C1 0.068(3) 0.068(4) 0.085(4) 0.012(3) 0.036(3) 0.003(3) C2 0.084(4) 0.103(5) 0.050(3) 0.003(3) 0.027(3) -0.009(3) C3 0.095(4) 0.086(4) 0.071(3) -0.019(3) 0.031(3) -0.035(4) C4 0.132(6) 0.069(4) 0.084(4) 0.008(3) 0.043(4) -0.027(4) C5 0.080(4) 0.090(4) 0.074(3) -0.009(3) 0.036(3) -0.017(3) C6 0.100(5) 0.075(4) 0.094(5) 0.009(4) 0.060(4) -0.003(3) C7 0.113(5) 0.056(4) 0.125(5) 0.014(3) 0.079(4) -0.002(3) C8 0.121(6) 0.050(4) 0.140(6) 0.002(4) 0.055(5) 0.009(4) C21 0.078(3) 0.047(3) 0.067(3) 0.006(2) 0.040(3) 0.007(2) C22 0.055(3) 0.051(3) 0.066(3) 0.000(2) 0.028(2) -0.011(2) C23 0.115(5) 0.068(4) 0.047(3) -0.008(3) 0.028(3) -0.015(3) C24 0.111(5) 0.104(5) 0.064(3) -0.011(3) 0.045(3) 0.010(4) C25 0.117(5) 0.068(4) 0.084(4) 0.005(3) 0.056(4) 0.031(4) C26 0.104(4) 0.040(3) 0.070(4) -0.005(3) 0.026(3) -0.002(3) C27 0.160(7) 0.063(4) 0.125(6) -0.003(4) 0.110(5) 0.008(4) C28 0.170(8) 0.118(6) 0.135(7) 0.052(5) 0.117(6) 0.034(6) C31 0.066(3) 0.056(3) 0.057(3) -0.012(2) 0.028(2) -0.008(2) C32 0.062(3) 0.057(3) 0.065(3) 0.004(2) 0.018(2) 0.006(2) C33 0.084(4) 0.094(5) 0.090(4) 0.021(4) 0.036(3) 0.033(4) C34 0.112(5) 0.068(4) 0.082(4) 0.026(3) 0.037(4) -0.002(3) C35 0.079(4) 0.098(5) 0.090(4) 0.015(4) 0.049(3) 0.001(3) C36 0.074(4) 0.052(3) 0.092(4) 0.000(3) 0.058(3) -0.007(3) C37 0.076(3) 0.069(3) 0.085(4) 0.005(3) 0.051(3) -0.011(3) C38 0.132(6) 0.045(3) 0.126(6) 0.011(4) 0.056(5) -0.008(4) C41 0.069(3) 0.054(3) 0.058(3) 0.015(2) 0.028(2) 0.003(2) C42 0.057(3) 0.057(3) 0.061(3) 0.001(2) 0.019(2) -0.001(2) C43 0.065(3) 0.121(6) 0.124(6) 0.051(5) 0.048(4) 0.010(4) C44 0.102(5) 0.091(5) 0.088(4) 0.014(4) 0.067(4) 0.008(4) C45 0.118(5) 0.099(5) 0.093(4) -0.010(4) 0.077(4) -0.005(4) C46 0.083(4) 0.101(5) 0.078(4) 0.003(4) 0.034(3) -0.033(4) C47 0.072(3) 0.058(3) 0.096(4) 0.003(3) 0.045(3) -0.008(3) C48 0.071(3) 0.120(5) 0.080(4) -0.032(4) 0.051(3) -0.001(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 C1 1.377(7) . ? O1 C5 1.460(7) . ? O2 C6 1.373(8) . ? O2 C2 1.461(7) . ? O3 C6 1.196(8) . ? O4 C8 1.347(9) . ? O4 C7 1.382(9) . ? O21 C21 1.412(6) . ? O21 C25 1.436(7) . ? O22 C26 1.341(7) . ? O22 C22 1.470(6) . ? O23 C26 1.211(7) . ? O24 C27 1.364(8) . ? O24 C28 1.472(9) . ? O31 C35 1.413(7) . ? O31 C31 1.435(6) . ? O32 C36 1.378(7) . ? O32 C32 1.455(6) . ? O33 C36 1.192(7) . ? O34 C37 1.455(8) . ? O34 C38 1.460(8) . ? O41 C41 1.386(6) . ? O41 C45 1.475(7) . ? O42 C46 1.308(8) . ? O42 C42 1.416(6) . ? O43 C46 1.188(8) . ? O44 C48 1.392(7) . ? O44 C47 1.401(7) . ? C1 C7 1.515(9) . ? C1 C2 1.535(9) . ? C1 H1 0.9800 . ? C2 C3 1.571(10) . ? C2 H2 0.9800 . ? C3 C4 1.494(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.475(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C28 1.547(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C46 1.523(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C21 C27 1.490(8) . ? C21 C22 1.512(7) . ? C21 H21 0.9800 . ? C22 C23 1.533(8) . ? C22 H22 0.9800 . ? C23 C24 1.467(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.599(10) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C38 1.482(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C31 C37 1.486(8) . ? C31 C32 1.540(7) . ? C31 H31 0.9800 . ? C32 C33 1.535(9) . ? C32 H32 0.9800 . ? C33 C34 1.504(10) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.524(10) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C48 1.521(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C41 C42 1.507(7) . ? C41 C47 1.549(8) . ? C41 H41 0.9800 . ? C42 C43 1.547(10) . ? C42 H42 0.9800 . ? C43 C44 1.559(11) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.461(10) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? 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 C1 O1 C5 114.0(5) . . ? C6 O2 C2 116.9(5) . . ? C8 O4 C7 115.7(6) . . ? C21 O21 C25 113.6(4) . . ? C26 O22 C22 118.3(4) . . ? C27 O24 C28 110.9(5) . . ? C35 O31 C31 109.0(4) . . ? C36 O32 C32 116.0(4) . . ? C37 O34 C38 113.0(5) . . ? C41 O41 C45 111.2(4) . . ? C46 O42 C42 118.8(4) . . ? C48 O44 C47 114.0(5) . . ? O1 C1 C7 108.4(5) . . ? O1 C1 C2 111.3(5) . . ? C7 C1 C2 112.1(5) . . ? O1 C1 H1 108.3 . . ? C7 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? O2 C2 C1 107.5(5) . . ? O2 C2 C3 107.3(6) . . ? C1 C2 C3 111.3(5) . . ? O2 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C4 C3 C2 109.7(5) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 113.9(6) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? O1 C5 C4 107.5(5) . . ? O1 C5 H5A 110.2 . . ? C4 C5 H5A 110.2 . . ? O1 C5 H5B 110.2 . . ? C4 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? O3 C6 O2 123.9(6) . . ? O3 C6 C28 129.5(7) . . ? O2 C6 C28 106.4(6) . . ? O4 C7 C1 108.8(5) . . ? O4 C7 H7A 109.9 . . ? C1 C7 H7A 109.9 . . ? O4 C7 H7B 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O4 C8 C46 112.5(7) . . ? O4 C8 H8A 109.1 . . ? C46 C8 H8A 109.1 . . ? O4 C8 H8B 109.1 . . ? C46 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O21 C21 C27 107.5(5) . . ? O21 C21 C22 113.5(4) . . ? C27 C21 C22 114.9(5) . . ? O21 C21 H21 106.8 . . ? C27 C21 H21 106.8 . . ? C22 C21 H21 106.8 . . ? O22 C22 C21 104.9(4) . . ? O22 C22 C23 108.3(4) . . ? C21 C22 C23 111.5(4) . . ? O22 C22 H22 110.6 . . ? C21 C22 H22 110.6 . . ? C23 C22 H22 110.6 . . ? C24 C23 C22 110.7(4) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 113.6(6) . . ? C23 C24 H24A 108.8 . . ? C25 C24 H24A 108.8 . . ? C23 C24 H24B 108.8 . . ? C25 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? O21 C25 C24 106.6(5) . . ? O21 C25 H25A 110.4 . . ? C24 C25 H25A 110.4 . . ? O21 C25 H25B 110.4 . . ? C24 C25 H25B 110.4 . . ? H25A C25 H25B 108.6 . . ? O23 C26 O22 123.6(5) . . ? O23 C26 C38 127.6(5) . . ? O22 C26 C38 108.7(5) . . ? O24 C27 C21 111.2(5) . . ? O24 C27 H27A 109.4 . . ? C21 C27 H27A 109.4 . . ? O24 C27 H27B 109.4 . . ? C21 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? O24 C28 C6 106.7(7) . . ? O24 C28 H28A 110.4 . . ? C6 C28 H28A 110.4 . . ? O24 C28 H28B 110.4 . . ? C6 C28 H28B 110.4 . . ? H28A C28 H28B 108.6 . . ? O31 C31 C37 108.0(4) . . ? O31 C31 C32 112.4(4) . . ? C37 C31 C32 112.2(4) . . ? O31 C31 H31 108.0 . . ? C37 C31 H31 108.0 . . ? C32 C31 H31 108.0 . . ? O32 C32 C33 109.7(5) . . ? O32 C32 C31 106.1(4) . . ? C33 C32 C31 110.6(5) . . ? O32 C32 H32 110.2 . . ? C33 C32 H32 110.2 . . ? C31 C32 H32 110.2 . . ? C34 C33 C32 111.8(5) . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33B 109.3 . . ? C32 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? C33 C34 C35 107.2(6) . . ? C33 C34 H34A 110.3 . . ? C35 C34 H34A 110.3 . . ? C33 C34 H34B 110.3 . . ? C35 C34 H34B 110.3 . . ? H34A C34 H34B 108.5 . . ? O31 C35 C34 111.8(5) . . ? O31 C35 H35A 109.3 . . ? C34 C35 H35A 109.3 . . ? O31 C35 H35B 109.3 . . ? C34 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? O33 C36 O32 124.1(6) . . ? O33 C36 C48 127.1(5) . . ? O32 C36 C48 108.8(5) . . ? O34 C37 C31 106.5(4) . . ? O34 C37 H37A 110.4 . . ? C31 C37 H37A 110.4 . . ? O34 C37 H37B 110.4 . . ? C31 C37 H37B 110.4 . . ? H37A C37 H37B 108.6 . . ? O34 C38 C26 108.5(6) . . ? O34 C38 H38A 110.0 . . ? C26 C38 H38A 110.0 . . ? O34 C38 H38B 110.0 . . ? C26 C38 H38B 110.0 . . ? H38A C38 H38B 108.4 . . ? O41 C41 C42 112.6(4) . . ? O41 C41 C47 106.4(4) . . ? C42 C41 C47 112.5(4) . . ? O41 C41 H41 108.4 . . ? C42 C41 H41 108.4 . . ? C47 C41 H41 108.4 . . ? O42 C42 C41 110.0(4) . . ? O42 C42 C43 109.5(5) . . ? C41 C42 C43 108.0(5) . . ? O42 C42 H42 109.8 . . ? C41 C42 H42 109.8 . . ? C43 C42 H42 109.8 . . ? C42 C43 C44 111.9(5) . . ? C42 C43 H43A 109.2 . . ? C44 C43 H43A 109.2 . . ? C42 C43 H43B 109.2 . . ? C44 C43 H43B 109.2 . . ? H43A C43 H43B 107.9 . . ? C45 C44 C43 109.1(5) . . ? C45 C44 H44A 109.9 . . ? C43 C44 H44A 109.9 . . ? C45 C44 H44B 109.9 . . ? C43 C44 H44B 109.9 . . ? H44A C44 H44B 108.3 . . ? C44 C45 O41 112.8(6) . . ? C44 C45 H45A 109.0 . . ? O41 C45 H45A 109.0 . . ? C44 C45 H45B 109.0 . . ? O41 C45 H45B 109.0 . . ? H45A C45 H45B 107.8 . . ? O43 C46 O42 123.8(7) . . ? O43 C46 C8 122.7(7) . . ? O42 C46 C8 113.2(6) . . ? O44 C47 C41 106.9(4) . . ? O44 C47 H47A 110.3 . . ? C41 C47 H47A 110.3 . . ? O44 C47 H47B 110.3 . . ? C41 C47 H47B 110.3 . . ? H47A C47 H47B 108.6 . . ? O44 C48 C36 111.9(5) . . ? O44 C48 H48A 109.2 . . ? C36 C48 H48A 109.2 . . ? O44 C48 H48B 109.2 . . ? C36 C48 H48B 109.2 . . ? H48A C48 H48B 107.9 . . ? 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 C5 O1 C1 C7 -175.3(5) . . . . ? C5 O1 C1 C2 60.9(6) . . . . ? C6 O2 C2 C1 142.4(5) . . . . ? C6 O2 C2 C3 -97.8(5) . . . . ? O1 C1 C2 O2 67.4(6) . . . . ? C7 C1 C2 O2 -54.2(6) . . . . ? O1 C1 C2 C3 -49.9(7) . . . . ? C7 C1 C2 C3 -171.5(5) . . . . ? O2 C2 C3 C4 -72.8(7) . . . . ? C1 C2 C3 C4 44.5(8) . . . . ? C2 C3 C4 C5 -51.0(8) . . . . ? C1 O1 C5 C4 -64.1(7) . . . . ? C3 C4 C5 O1 58.5(8) . . . . ? C2 O2 C6 O3 6.9(11) . . . . ? C2 O2 C6 C28 -176.6(6) . . . . ? C8 O4 C7 C1 -177.1(7) . . . . ? O1 C1 C7 O4 69.2(8) . . . . ? C2 C1 C7 O4 -167.5(6) . . . . ? C7 O4 C8 C46 -102.2(8) . . . . ? C25 O21 C21 C27 -171.3(5) . . . . ? C25 O21 C21 C22 60.4(6) . . . . ? C26 O22 C22 C21 158.9(5) . . . . ? C26 O22 C22 C23 -81.9(6) . . . . ? O21 C21 C22 O22 65.6(5) . . . . ? C27 C21 C22 O22 -58.7(7) . . . . ? O21 C21 C22 C23 -51.5(6) . . . . ? C27 C21 C22 C23 -175.8(6) . . . . ? O22 C22 C23 C24 -67.8(6) . . . . ? C21 C22 C23 C24 47.2(7) . . . . ? C22 C23 C24 C25 -50.8(7) . . . . ? C21 O21 C25 C24 -59.2(7) . . . . ? C23 C24 C25 O21 55.9(7) . . . . ? C22 O22 C26 O23 -1.2(10) . . . . ? C22 O22 C26 C38 175.3(5) . . . . ? C28 O24 C27 C21 -178.1(7) . . . . ? O21 C21 C27 O24 59.5(8) . . . . ? C22 C21 C27 O24 -173.0(6) . . . . ? C27 O24 C28 C6 -84.8(8) . . . . ? O3 C6 C28 O24 2.6(12) . . . . ? O2 C6 C28 O24 -173.5(5) . . . . ? C35 O31 C31 C37 -176.2(5) . . . . ? C35 O31 C31 C32 59.5(5) . . . . ? C36 O32 C32 C33 -97.3(5) . . . . ? C36 O32 C32 C31 143.3(4) . . . . ? O31 C31 C32 O32 68.0(5) . . . . ? C37 C31 C32 O32 -53.9(5) . . . . ? O31 C31 C32 C33 -50.8(6) . . . . ? C37 C31 C32 C33 -172.7(5) . . . . ? O32 C32 C33 C34 -68.1(6) . . . . ? C31 C32 C33 C34 48.5(7) . . . . ? C32 C33 C34 C35 -53.1(7) . . . . ? C31 O31 C35 C34 -66.6(6) . . . . ? C33 C34 C35 O31 63.2(7) . . . . ? C32 O32 C36 O33 -4.6(8) . . . . ? C32 O32 C36 C48 173.4(5) . . . . ? C38 O34 C37 C31 -177.9(5) . . . . ? O31 C31 C37 O34 64.4(5) . . . . ? C32 C31 C37 O34 -171.2(4) . . . . ? C37 O34 C38 C26 -89.6(7) . . . . ? O23 C26 C38 O34 10.5(11) . . . . ? O22 C26 C38 O34 -165.8(5) . . . . ? C45 O41 C41 C42 62.3(6) . . . . ? C45 O41 C41 C47 -174.0(5) . . . . ? C46 O42 C42 C41 160.6(5) . . . . ? C46 O42 C42 C43 -80.8(7) . . . . ? O41 C41 C42 O42 62.0(6) . . . . ? C47 C41 C42 O42 -58.3(6) . . . . ? O41 C41 C42 C43 -57.5(6) . . . . ? C47 C41 C42 C43 -177.7(5) . . . . ? O42 C42 C43 C44 -69.0(6) . . . . ? C41 C42 C43 C44 50.8(7) . . . . ? C42 C43 C44 C45 -50.6(8) . . . . ? C43 C44 C45 O41 54.0(8) . . . . ? C41 O41 C45 C44 -61.3(7) . . . . ? C42 O42 C46 O43 2.6(11) . . . . ? C42 O42 C46 C8 177.8(6) . . . . ? O4 C8 C46 O43 2.6(12) . . . . ? O4 C8 C46 O42 -172.7(6) . . . . ? C48 O44 C47 C41 -171.0(5) . . . . ? O41 C41 C47 O44 72.0(5) . . . . ? C42 C41 C47 O44 -164.2(4) . . . . ? C47 O44 C48 C36 -87.0(7) . . . . ? O33 C36 C48 O44 -4.9(10) . . . . ? O32 C36 C48 O44 177.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.217 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049 ####################### SQUEEZE RESULTS ####################### # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.061 0.239 0.220 279 25 'solvent massively disordered ' 2 -0.051 0.739 0.669 279 25 'solvent massively disordered ' # Attachment 'Macrotetraolide_4.cif' data_MACROTETRAOLIDE_4_(revised) _database_code_depnum_ccdc_archive 'CCDC 776409' #TrackingRef 'Macrotetraolide_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H48 O16' _chemical_formula_sum 'C32 H48 O16' _chemical_formula_weight 688.70 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 '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 _symmetry_space_group_name_Hall C2y loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.443(7) _cell_length_b 7.313(5) _cell_length_c 15.038(6) _cell_angle_alpha 90.00 _cell_angle_beta 122.19(5) _cell_angle_gamma 90.00 _cell_volume 1716.5(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2090 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2090 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et atl., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A. L. Spek, 2003)' _computing_publication_material ? _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^)+(0.0441P)^2^+0.3777P] 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 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2090 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.73088(12) -0.5998(3) 0.32812(14) 0.0557(5) Uani 1 1 d . . . O2 O 0.74021(9) -0.2816(2) 0.14906(12) 0.0421(4) Uani 1 1 d . . . O3 O 0.62965(11) -0.0860(3) 0.06726(17) 0.0680(6) Uani 1 1 d . . . O4 O 0.77091(9) -0.2257(3) 0.39084(12) 0.0501(5) Uani 1 1 d . . . O21 O 1.10745(9) 0.3033(2) 0.80816(13) 0.0447(4) Uani 1 1 d . . . O22 O 0.92643(9) 0.0249(2) 0.61795(11) 0.0430(4) Uani 1 1 d . . . O23 O 0.88796(12) 0.0652(4) 0.44978(13) 0.0663(6) Uani 1 1 d . . . O24 O 1.15900(9) -0.0747(2) 0.88625(11) 0.0439(4) Uani 1 1 d . . . C1 C 0.76681(14) -0.4792(4) 0.28734(17) 0.0408(5) Uani 1 1 d . . . H1 H 0.8029 -0.5507 0.2704 0.049 Uiso 1 1 calc R . . C2 C 0.69545(13) -0.3902(4) 0.18692(17) 0.0404(5) Uani 1 1 d . . . H2 H 0.6613 -0.3101 0.2029 0.049 Uiso 1 1 calc R . . C3 C 0.63818(18) -0.5317(4) 0.1060(2) 0.0562(7) Uani 1 1 d . . . H3A H 0.6696 -0.5949 0.0801 0.067 Uiso 1 1 calc R . . H3B H 0.5891 -0.4720 0.0471 0.067 Uiso 1 1 calc R . . C4 C 0.60788(18) -0.6689(4) 0.1559(2) 0.0629(8) Uani 1 1 d . . . H4A H 0.5687 -0.6095 0.1713 0.075 Uiso 1 1 calc R . . H4B H 0.5775 -0.7683 0.1072 0.075 Uiso 1 1 calc R . . C5 C 0.6833(2) -0.7436(4) 0.2557(2) 0.0630(8) Uani 1 1 d . . . H5A H 0.6633 -0.8283 0.2877 0.076 Uiso 1 1 calc R . . H5B H 0.7204 -0.8101 0.2394 0.076 Uiso 1 1 calc R . . C6 C 0.70087(14) -0.1321(4) 0.09329(17) 0.0420(5) Uani 1 1 d . . . C7 C 0.75401(14) -0.0255(4) 0.06241(18) 0.0474(6) Uani 1 1 d . . . H7A H 0.7286 -0.0395 -0.0127 0.057 Uiso 1 1 calc R . . H7B H 0.7507 0.1031 0.0758 0.057 Uiso 1 1 calc R . . C8 C 0.82265(13) -0.3449(4) 0.37242(18) 0.0450(6) Uani 1 1 d . . . H8A H 0.8624 -0.4101 0.4365 0.054 Uiso 1 1 calc R . . H8B H 0.8557 -0.2741 0.3516 0.054 Uiso 1 1 calc R . . C21 C 1.05300(12) 0.1466(3) 0.76717(16) 0.0349(5) Uani 1 1 d . . . H21 H 1.0261 0.1254 0.8076 0.042 Uiso 1 1 calc R . . C22 C 0.98331(12) 0.1827(3) 0.65226(16) 0.0366(5) Uani 1 1 d . . . H22 H 1.0089 0.1943 0.6098 0.044 Uiso 1 1 calc R . . C23 C 0.93277(13) 0.3534(4) 0.64184(19) 0.0462(6) Uani 1 1 d . . . H23A H 0.9004 0.3338 0.6750 0.055 Uiso 1 1 calc R . . H23B H 0.8926 0.3802 0.5681 0.055 Uiso 1 1 calc R . . C24 C 0.99371(15) 0.5131(4) 0.6938(2) 0.0542(7) Uani 1 1 d . . . H24A H 1.0198 0.5437 0.6543 0.065 Uiso 1 1 calc R . . H24B H 0.9621 0.6191 0.6938 0.065 Uiso 1 1 calc R . . C25 C 1.06247(16) 0.4656(4) 0.8051(2) 0.0554(7) Uani 1 1 d . . . H25A H 1.1026 0.5664 0.8360 0.066 Uiso 1 1 calc R . . H25B H 1.0367 0.4468 0.8463 0.066 Uiso 1 1 calc R . . C26 C 0.87923(13) -0.0100(4) 0.51425(16) 0.0415(6) Uani 1 1 d . . . C27 C 0.81351(14) -0.1539(4) 0.49315(19) 0.0505(7) Uani 1 1 d . . . H27A H 0.8416 -0.2532 0.5428 0.061 Uiso 1 1 calc R . . H27B H 0.7714 -0.1015 0.5056 0.061 Uiso 1 1 calc R . . C28 C 1.10823(14) -0.0152(3) 0.77973(17) 0.0419(6) Uani 1 1 d . . . H28A H 1.0719 -0.1151 0.7365 0.050 Uiso 1 1 calc R . . H28B H 1.1456 0.0175 0.7552 0.050 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 0.0738(11) 0.0580(12) 0.0518(10) -0.0031(9) 0.0445(9) -0.0112(10) O2 0.0376(7) 0.0528(10) 0.0371(8) 0.0045(8) 0.0207(6) 0.0013(7) O3 0.0463(10) 0.0750(15) 0.0777(14) 0.0158(12) 0.0296(9) 0.0163(10) O4 0.0330(7) 0.0719(12) 0.0350(8) -0.0186(9) 0.0110(6) -0.0019(8) O21 0.0314(7) 0.0421(9) 0.0418(9) -0.0040(7) 0.0069(7) -0.0025(7) O22 0.0382(8) 0.0559(11) 0.0280(7) -0.0047(7) 0.0130(6) -0.0147(8) O23 0.0706(11) 0.0912(16) 0.0349(9) -0.0050(10) 0.0267(8) -0.0239(12) O24 0.0415(8) 0.0533(10) 0.0329(8) 0.0082(8) 0.0172(6) 0.0065(8) C1 0.0444(11) 0.0466(14) 0.0398(11) -0.0009(11) 0.0280(10) -0.0002(11) C2 0.0381(10) 0.0533(14) 0.0340(11) -0.0055(10) 0.0219(9) -0.0029(10) C3 0.0540(14) 0.0679(18) 0.0455(14) -0.0145(13) 0.0258(11) -0.0132(14) C4 0.0632(16) 0.065(2) 0.0721(19) -0.0233(16) 0.0438(15) -0.0229(15) C5 0.0818(19) 0.0538(17) 0.0749(19) -0.0103(16) 0.0561(17) -0.0170(16) C6 0.0370(11) 0.0488(14) 0.0303(10) -0.0035(10) 0.0113(8) 0.0015(10) C7 0.0453(11) 0.0520(15) 0.0325(11) 0.0046(11) 0.0125(9) -0.0006(11) C8 0.0360(10) 0.0617(16) 0.0346(11) 0.0003(11) 0.0169(9) 0.0014(11) C21 0.0289(9) 0.0416(12) 0.0280(10) -0.0017(9) 0.0109(8) -0.0022(9) C22 0.0295(9) 0.0465(13) 0.0288(10) 0.0002(10) 0.0121(8) -0.0066(10) C23 0.0302(10) 0.0549(15) 0.0410(12) 0.0060(12) 0.0106(9) 0.0018(11) C24 0.0397(12) 0.0487(15) 0.0584(15) 0.0067(13) 0.0154(11) 0.0062(12) C25 0.0473(12) 0.0452(15) 0.0505(14) -0.0097(12) 0.0105(11) 0.0003(12) C26 0.0332(10) 0.0589(16) 0.0274(10) -0.0032(10) 0.0128(8) -0.0020(10) C27 0.0385(11) 0.0744(19) 0.0364(12) -0.0183(12) 0.0183(10) -0.0151(12) C28 0.0404(11) 0.0472(15) 0.0306(11) -0.0012(10) 0.0139(9) 0.0014(10) _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 C1 1.423(4) . ? O1 C5 1.430(4) . ? O2 C6 1.333(3) . ? O2 C2 1.462(4) . ? O3 C6 1.202(5) . ? O4 C27 1.404(6) . ? O4 C8 1.425(4) . ? O21 C21 1.429(3) . ? O21 C25 1.435(4) . ? O22 C26 1.345(6) . ? O22 C22 1.456(4) . ? O23 C26 1.198(4) . ? O24 C7 1.407(6) 2_756 ? O24 C28 1.426(6) . ? C1 C8 1.503(4) . ? C1 C2 1.523(5) . ? C1 H1 0.9800 . ? C2 C3 1.516(4) . ? C2 H2 0.9800 . ? C3 C4 1.526(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.503(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.506(5) . ? C7 O24 1.407(6) 2_756 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C21 C28 1.506(4) . ? C21 C22 1.530(6) . ? C21 H21 0.9800 . ? C22 C23 1.515(4) . ? C22 H22 0.9800 . ? C23 C24 1.518(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.506(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.506(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? 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 C1 O1 C5 111.4(3) . . ? C6 O2 C2 117.4(3) . . ? C27 O4 C8 113.6(2) . . ? C21 O21 C25 112.9(3) . . ? C26 O22 C22 117.40(19) . . ? C7 O24 C28 114.36(19) 2_756 . ? O1 C1 C8 107.7(3) . . ? O1 C1 C2 109.7(3) . . ? C8 C1 C2 113.8(3) . . ? O1 C1 H1 108.5 . . ? C8 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? O2 C2 C3 110.8(3) . . ? O2 C2 C1 104.4(3) . . ? C3 C2 C1 111.6(3) . . ? O2 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C2 C3 C4 109.6(3) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 110.0(3) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? O1 C5 C4 111.0(3) . . ? O1 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? O1 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? O3 C6 O2 124.7(2) . . ? O3 C6 C7 122.2(3) . . ? O2 C6 C7 113.1(3) . . ? O24 C7 C6 115.9(3) 2_756 . ? O24 C7 H7A 108.3 2_756 . ? C6 C7 H7A 108.3 . . ? O24 C7 H7B 108.3 2_756 . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O4 C8 C1 109.8(3) . . ? O4 C8 H8A 109.7 . . ? C1 C8 H8A 109.7 . . ? O4 C8 H8B 109.7 . . ? C1 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O21 C21 C28 107.6(3) . . ? O21 C21 C22 108.9(2) . . ? C28 C21 C22 112.5(2) . . ? O21 C21 H21 109.3 . . ? C28 C21 H21 109.3 . . ? C22 C21 H21 109.3 . . ? O22 C22 C23 109.2(3) . . ? O22 C22 C21 106.1(2) . . ? C23 C22 C21 111.1(2) . . ? O22 C22 H22 110.1 . . ? C23 C22 H22 110.1 . . ? C21 C22 H22 110.1 . . ? C22 C23 C24 109.6(3) . . ? C22 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? C22 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? C25 C24 C23 110.4(2) . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? O21 C25 C24 110.9(3) . . ? O21 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? O21 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? O23 C26 O22 124.6(3) . . ? O23 C26 C27 126.2(2) . . ? O22 C26 C27 109.1(2) . . ? O4 C27 C26 114.2(2) . . ? O4 C27 H27A 108.7 . . ? C26 C27 H27A 108.7 . . ? O4 C27 H27B 108.7 . . ? C26 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? O24 C28 C21 112.1(2) . . ? O24 C28 H28A 109.2 . . ? C21 C28 H28A 109.2 . . ? O24 C28 H28B 109.2 . . ? C21 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? 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 C5 O1 C1 C8 -174.3(2) . . . . ? C5 O1 C1 C2 61.4(3) . . . . ? C6 O2 C2 C3 88.5(3) . . . . ? C6 O2 C2 C1 -151.1(2) . . . . ? O1 C1 C2 O2 -175.98(18) . . . . ? C8 C1 C2 O2 63.4(3) . . . . ? O1 C1 C2 C3 -56.2(3) . . . . ? C8 C1 C2 C3 -176.85(19) . . . . ? O2 C2 C3 C4 167.6(2) . . . . ? C1 C2 C3 C4 51.7(3) . . . . ? C2 C3 C4 C5 -51.9(3) . . . . ? C1 O1 C5 C4 -63.3(4) . . . . ? C3 C4 C5 O1 57.7(3) . . . . ? C2 O2 C6 O3 -4.2(3) . . . . ? C2 O2 C6 C7 177.34(19) . . . . ? O3 C6 C7 O24 168.7(2) . . . 2_756 ? O2 C6 C7 O24 -12.8(3) . . . 2_756 ? C27 O4 C8 C1 153.4(2) . . . . ? O1 C1 C8 O4 -69.0(3) . . . . ? C2 C1 C8 O4 52.8(3) . . . . ? C25 O21 C21 C28 -177.2(2) . . . . ? C25 O21 C21 C22 60.6(3) . . . . ? C26 O22 C22 C23 83.3(2) . . . . ? C26 O22 C22 C21 -156.9(2) . . . . ? O21 C21 C22 O22 -175.59(16) . . . . ? C28 C21 C22 O22 65.2(3) . . . . ? O21 C21 C22 C23 -57.1(3) . . . . ? C28 C21 C22 C23 -176.27(19) . . . . ? O22 C22 C23 C24 170.72(19) . . . . ? C21 C22 C23 C24 54.1(3) . . . . ? C22 C23 C24 C25 -53.2(3) . . . . ? C21 O21 C25 C24 -61.2(3) . . . . ? C23 C24 C25 O21 56.1(3) . . . . ? C22 O22 C26 O23 9.4(4) . . . . ? C22 O22 C26 C27 -169.38(19) . . . . ? C8 O4 C27 C26 73.2(4) . . . . ? O23 C26 C27 O4 12.3(4) . . . . ? O22 C26 C27 O4 -168.9(2) . . . . ? C7 O24 C28 C21 -104.4(3) 2_756 . . . ? O21 C21 C28 O24 74.0(2) . . . . ? C22 C21 C28 O24 -166.11(19) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.167 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032