Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Peter Junk' _publ_contact_author_address ; School of Chemistry Monash University Box 23 Clayton Victoria 3800 AUSTRALIA ; _publ_contact_author_email PETER.JUNK@SCI.MONASH.EDU.AU _publ_section_title ; Synthesis and Structural Characterisation of Lithium and Sodium 2,6-Dibenzylphenolate Complexes ; loop_ _publ_author_name 'Peter Junk' 'Marcus L. Cole' 'Kathryn M. Proctor' 'Janet Scott' 'Christopher R. Strauss' # Attachment 'Combined KP Li Na CIF updated (28.03)1.txt' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 299151' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 396 _chemical_formula_moiety 'C48 H54 Li2 O4' _chemical_formula_sum 'C48 H54 Li2 O4' _chemical_formula_weight 708.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4436(19) _cell_length_b 10.290(2) _cell_length_c 11.684(2) _cell_angle_alpha 77.75(3) _cell_angle_beta 89.93(3) _cell_angle_gamma 68.08(3) _cell_volume 1025.5(4) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9792 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13933 _diffrn_reflns_av_R_equivalents 0.2431 _diffrn_reflns_av_sigmaI/netI 0.2899 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.80 _reflns_number_total 4652 _reflns_number_gt 1435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.1638P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4652 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2780 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.2971 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 0.776 _refine_ls_restrained_S_all 0.776 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4967(3) 1.1173(3) -0.0841(2) 0.0401(8) Uani 1 1 d . . . O2 O 0.6434(4) 1.1086(3) 0.1723(3) 0.0436(9) Uani 1 1 d . . . C1 C 0.4552(5) 1.2390(5) -0.1674(4) 0.0369(12) Uani 1 1 d . . . C2 C 0.3067(5) 1.3471(5) -0.1745(4) 0.0359(11) Uani 1 1 d . . . C3 C 0.2657(5) 1.4703(5) -0.2640(4) 0.0421(12) Uani 1 1 d . . . H3 H 0.1661 1.5428 -0.2691 0.051 Uiso 1 1 calc R . . C4 C 0.3655(5) 1.4908(5) -0.3461(4) 0.0419(12) Uani 1 1 d . . . H4 H 0.3347 1.5763 -0.4065 0.050 Uiso 1 1 calc R . . C5 C 0.5115(5) 1.3849(5) -0.3393(4) 0.0393(12) Uani 1 1 d . . . H5 H 0.5803 1.3984 -0.3956 0.047 Uiso 1 1 calc R . . C6 C 0.5579(5) 1.2594(5) -0.2512(4) 0.0359(11) Uani 1 1 d . . . C7 C 0.1985(5) 1.3249(5) -0.0855(4) 0.0428(12) Uani 1 1 d . . . H7A H 0.1951 1.2290 -0.0811 0.051 Uiso 1 1 calc R . . H7B H 0.0945 1.3976 -0.1136 0.051 Uiso 1 1 calc R . . C8 C 0.2377(5) 1.3346(5) 0.0370(4) 0.0370(12) Uani 1 1 d . . . C9 C 0.2024(5) 1.2552(5) 0.1357(4) 0.0448(13) Uani 1 1 d . . . H9 H 0.1571 1.1893 0.1266 0.054 Uiso 1 1 calc R . . C10 C 0.2318(6) 1.2696(6) 0.2474(5) 0.0529(14) Uani 1 1 d . . . H10 H 0.2049 1.2152 0.3138 0.064 Uiso 1 1 calc R . . C11 C 0.3001(6) 1.3629(6) 0.2626(5) 0.0563(15) Uani 1 1 d . . . H11 H 0.3208 1.3725 0.3392 0.068 Uiso 1 1 calc R . . C12 C 0.3380(6) 1.4416(6) 0.1660(5) 0.0563(15) Uani 1 1 d . . . H12 H 0.3849 1.5062 0.1757 0.068 Uiso 1 1 calc R . . C13 C 0.3078(6) 1.4270(5) 0.0540(4) 0.0488(14) Uani 1 1 d . . . H13 H 0.3356 1.4812 -0.0122 0.059 Uiso 1 1 calc R . . C14 C 0.7158(5) 1.1423(5) -0.2422(4) 0.0420(12) Uani 1 1 d . . . H14A H 0.7603 1.1139 -0.1597 0.050 Uiso 1 1 calc R . . H14B H 0.7050 1.0571 -0.2615 0.050 Uiso 1 1 calc R . . C15 C 0.8264(5) 1.1832(5) -0.3210(4) 0.0357(11) Uani 1 1 d . . . C16 C 0.8505(5) 1.1488(5) -0.4296(4) 0.0404(12) Uani 1 1 d . . . H16 H 0.8024 1.0915 -0.4535 0.049 Uiso 1 1 calc R . . C17 C 0.9444(5) 1.1973(5) -0.5043(4) 0.0463(13) Uani 1 1 d . . . H17 H 0.9595 1.1728 -0.5786 0.056 Uiso 1 1 calc R . . C18 C 1.0145(5) 1.2793(5) -0.4719(4) 0.0456(13) Uani 1 1 d . . . H18 H 1.0759 1.3142 -0.5244 0.055 Uiso 1 1 calc R . . C19 C 0.9966(5) 1.3118(5) -0.3626(4) 0.0469(13) Uani 1 1 d . . . H19 H 1.0483 1.3662 -0.3384 0.056 Uiso 1 1 calc R . . C20 C 0.9020(5) 1.2642(5) -0.2884(4) 0.0425(12) Uani 1 1 d . . . H20 H 0.8889 1.2875 -0.2137 0.051 Uiso 1 1 calc R . . C21 C 0.6874(6) 1.0696(5) 0.2960(4) 0.0484(14) Uani 1 1 d . . . H21A H 0.6551 1.1569 0.3282 0.058 Uiso 1 1 calc R . . H21B H 0.8002 1.0204 0.3105 0.058 Uiso 1 1 calc R . . C22 C 0.6119(5) 0.9710(5) 0.3550(4) 0.0504(14) Uani 1 1 d . . . H22A H 0.5005 1.0196 0.3387 0.076 Uiso 1 1 calc R . . H22B H 0.6385 0.9458 0.4401 0.076 Uiso 1 1 calc R . . H22C H 0.6475 0.8833 0.3248 0.076 Uiso 1 1 calc R . . C23 C 0.7040(6) 1.2089(6) 0.1084(5) 0.0527(14) Uani 1 1 d . . . H23A H 0.6912 1.2846 0.1521 0.063 Uiso 1 1 calc R . . H23B H 0.6444 1.2559 0.0311 0.063 Uiso 1 1 calc R . . C24 C 0.8688(6) 1.1398(7) 0.0898(5) 0.083(2) Uani 1 1 d . . . H24A H 0.9302 1.1050 0.1657 0.124 Uiso 1 1 calc R . . H24B H 0.9010 1.2103 0.0382 0.124 Uiso 1 1 calc R . . H24C H 0.8839 1.0587 0.0534 0.124 Uiso 1 1 calc R . . Li1 Li 0.5094(9) 1.0608(9) 0.0782(7) 0.045(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.048(2) 0.0332(18) 0.0336(18) 0.0027(15) -0.0029(15) -0.0144(16) O2 0.049(2) 0.041(2) 0.039(2) -0.0003(16) 0.0011(16) -0.0198(17) C1 0.044(3) 0.028(3) 0.032(3) 0.003(2) -0.002(2) -0.011(2) C2 0.034(3) 0.031(3) 0.036(3) 0.002(2) -0.002(2) -0.011(2) C3 0.038(3) 0.038(3) 0.041(3) 0.000(2) 0.001(2) -0.008(2) C4 0.046(3) 0.032(3) 0.038(3) 0.005(2) -0.001(2) -0.010(3) C5 0.036(3) 0.030(3) 0.040(3) 0.003(2) 0.001(2) -0.004(2) C6 0.032(3) 0.033(3) 0.036(3) -0.001(2) 0.001(2) -0.008(2) C7 0.036(3) 0.044(3) 0.043(3) -0.003(2) 0.004(2) -0.013(2) C8 0.038(3) 0.031(3) 0.036(3) -0.007(2) 0.004(2) -0.007(2) C9 0.049(3) 0.037(3) 0.041(3) -0.003(2) 0.010(2) -0.012(3) C10 0.056(3) 0.049(3) 0.040(3) -0.004(3) 0.016(3) -0.008(3) C11 0.064(4) 0.047(3) 0.043(3) -0.012(3) 0.006(3) -0.004(3) C12 0.064(4) 0.054(4) 0.052(4) -0.018(3) 0.004(3) -0.020(3) C13 0.059(3) 0.043(3) 0.043(3) -0.008(3) 0.010(3) -0.018(3) C14 0.038(3) 0.033(3) 0.046(3) -0.002(2) 0.002(2) -0.008(2) C15 0.039(3) 0.026(3) 0.032(3) -0.003(2) 0.000(2) -0.003(2) C16 0.042(3) 0.028(3) 0.043(3) -0.006(2) -0.002(2) -0.007(2) C17 0.044(3) 0.043(3) 0.036(3) -0.003(2) 0.005(2) -0.001(3) C18 0.039(3) 0.040(3) 0.047(3) -0.002(3) 0.007(2) -0.008(3) C19 0.041(3) 0.048(3) 0.049(3) -0.007(3) 0.003(2) -0.017(3) C20 0.043(3) 0.039(3) 0.041(3) -0.013(2) 0.004(2) -0.009(3) C21 0.059(3) 0.046(3) 0.033(3) -0.001(2) -0.009(2) -0.017(3) C22 0.047(3) 0.054(3) 0.044(3) -0.005(3) 0.002(2) -0.015(3) C23 0.050(3) 0.055(3) 0.054(3) 0.002(3) -0.002(3) -0.028(3) C24 0.038(4) 0.106(5) 0.081(5) 0.019(4) 0.000(3) -0.024(4) Li1 0.048(5) 0.045(5) 0.040(5) -0.002(4) 0.005(4) -0.018(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 1.337(5) . ? O1 Li1 1.851(8) . ? O1 Li1 1.842(9) 2_675 ? O2 C21 1.434(5) . ? O2 C23 1.436(5) . ? O2 Li1 1.935(9) . ? C1 C6 1.417(6) . ? C1 C2 1.416(6) . ? C2 C3 1.387(6) . ? C2 C7 1.500(6) . ? C3 C4 1.383(6) . ? C4 C5 1.392(6) . ? C5 C6 1.390(6) . ? C6 C14 1.514(6) . ? C7 C8 1.511(6) . ? C8 C9 1.382(6) . ? C8 C13 1.390(6) . ? C9 C10 1.385(7) . ? C10 C11 1.379(7) . ? C11 C12 1.373(7) . ? C12 C13 1.391(7) . ? C14 C15 1.509(6) . ? C15 C16 1.385(6) . ? C15 C20 1.389(6) . ? C16 C17 1.393(6) . ? C17 C18 1.359(7) . ? C18 C19 1.382(7) . ? C19 C20 1.391(6) . ? C21 C22 1.502(6) . ? C23 C24 1.488(7) . ? Li1 O1 1.842(9) 2_675 ? Li1 Li1 2.465(17) 2_675 ? 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 Li1 138.6(4) . . ? C1 O1 Li1 133.7(4) . 2_675 ? Li1 O1 Li1 83.7(4) . 2_675 ? C21 O2 C23 112.8(4) . . ? C21 O2 Li1 132.2(3) . . ? C23 O2 Li1 114.8(3) . . ? O1 C1 C6 120.3(4) . . ? O1 C1 C2 120.3(4) . . ? C6 C1 C2 119.4(4) . . ? C3 C2 C1 118.9(4) . . ? C3 C2 C7 122.0(4) . . ? C1 C2 C7 119.2(4) . . ? C4 C3 C2 122.0(4) . . ? C3 C4 C5 119.3(4) . . ? C4 C5 C6 120.9(4) . . ? C5 C6 C1 119.6(4) . . ? C5 C6 C14 121.9(4) . . ? C1 C6 C14 118.5(4) . . ? C2 C7 C8 115.3(4) . . ? C9 C8 C13 117.6(4) . . ? C9 C8 C7 121.6(4) . . ? C13 C8 C7 120.8(4) . . ? C10 C9 C8 121.4(5) . . ? C11 C10 C9 120.2(5) . . ? C10 C11 C12 119.4(5) . . ? C11 C12 C13 120.1(5) . . ? C12 C13 C8 121.2(5) . . ? C15 C14 C6 114.9(4) . . ? C16 C15 C20 117.6(4) . . ? C16 C15 C14 122.1(4) . . ? C20 C15 C14 120.2(4) . . ? C15 C16 C17 120.8(5) . . ? C18 C17 C16 120.6(5) . . ? C17 C18 C19 120.0(5) . . ? C18 C19 C20 119.3(5) . . ? C19 C20 C15 121.6(5) . . ? O2 C21 C22 108.6(4) . . ? O2 C23 C24 112.9(4) . . ? O1 Li1 O1 96.3(4) . 2_675 ? O1 Li1 O2 119.5(4) . . ? O1 Li1 O2 128.0(4) 2_675 . ? O1 Li1 Li1 48.0(3) . 2_675 ? O1 Li1 Li1 48.3(3) 2_675 2_675 ? O2 Li1 Li1 146.1(6) . 2_675 ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.190 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.052 _chemical_compound_source Et2O #===END data_COMPOUND_2 _database_code_depnum_ccdc_archive 'CCDC 299152' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 385 _chemical_formula_moiety 'C48 H54 Li2 O6' _chemical_formula_sum 'C48 H54 Li2 O6' _chemical_formula_weight 740.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5653(2) _cell_length_b 13.4617(2) _cell_length_c 14.4056(3) _cell_angle_alpha 91.8320(10) _cell_angle_beta 112.2690(10) _cell_angle_gamma 92.0970(10) _cell_volume 2071.57(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9703 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24711 _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 28.00 _reflns_number_total 9853 _reflns_number_gt 6962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0971P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9853 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.90908(9) 0.62660(6) 0.22577(7) 0.0236(2) Uani 1 1 d . . . O2 O 0.80482(9) 0.81162(7) 0.21118(7) 0.0237(2) Uani 1 1 d . . . O3 O 0.94794(10) 0.71106(7) 0.44231(7) 0.0280(2) Uani 1 1 d . . . O4 O 1.07624(10) 0.86611(7) 0.39926(7) 0.0280(2) Uani 1 1 d . . . O5 O 0.60393(9) 0.70253(7) 0.01721(7) 0.0272(2) Uani 1 1 d . . . O6 O 0.81857(9) 0.66438(7) -0.00361(7) 0.0267(2) Uani 1 1 d . . . C1 C 0.95726(14) 0.53848(9) 0.23648(10) 0.0223(3) Uani 1 1 d . . . C2 C 1.08802(14) 0.52814(10) 0.28645(10) 0.0248(3) Uani 1 1 d . . . C3 C 1.13716(16) 0.43416(11) 0.29752(11) 0.0314(3) Uani 1 1 d . . . H3 H 1.2245 0.4286 0.3324 0.038 Uiso 1 1 calc R . . C4 C 1.06108(17) 0.34871(11) 0.25864(12) 0.0361(4) Uani 1 1 d . . . H4 H 1.0956 0.2851 0.2658 0.043 Uiso 1 1 calc R . . C5 C 0.93382(17) 0.35805(10) 0.20923(12) 0.0342(4) Uani 1 1 d . . . H5 H 0.8814 0.2999 0.1813 0.041 Uiso 1 1 calc R . . C6 C 0.88013(15) 0.44993(10) 0.19908(10) 0.0268(3) Uani 1 1 d . . . C7 C 1.17470(14) 0.61998(10) 0.32255(10) 0.0262(3) Uani 1 1 d . . . H7A H 1.2559 0.6016 0.3727 0.031 Uiso 1 1 calc R . . H7B H 1.1383 0.6680 0.3559 0.031 Uiso 1 1 calc R . . C8 C 1.19617(12) 0.66878(10) 0.23690(10) 0.0230(3) Uani 1 1 d . . . C9 C 1.15275(13) 0.76162(10) 0.20504(11) 0.0267(3) Uani 1 1 d . . . H9 H 1.1098 0.7971 0.2391 0.032 Uiso 1 1 calc R . . C10 C 1.17098(14) 0.80338(11) 0.12443(12) 0.0293(3) Uani 1 1 d . . . H10 H 1.1410 0.8671 0.1040 0.035 Uiso 1 1 calc R . . C11 C 1.23241(15) 0.75254(11) 0.07401(12) 0.0324(3) Uani 1 1 d . . . H11 H 1.2441 0.7806 0.0183 0.039 Uiso 1 1 calc R . . C12 C 1.27713(16) 0.65996(11) 0.10520(13) 0.0359(4) Uani 1 1 d . . . H12 H 1.3203 0.6248 0.0711 0.043 Uiso 1 1 calc R . . C13 C 1.25908(14) 0.61874(10) 0.18559(12) 0.0290(3) Uani 1 1 d . . . H13 H 1.2900 0.5553 0.2062 0.035 Uiso 1 1 calc R . . C14 C 0.73944(15) 0.45590(11) 0.15381(11) 0.0311(3) Uani 1 1 d . . . H14A H 0.7180 0.5147 0.1122 0.037 Uiso 1 1 calc R . . H14B H 0.7020 0.3959 0.1094 0.037 Uiso 1 1 calc R . . C15 C 0.68429(13) 0.46360(10) 0.23356(11) 0.0274(3) Uani 1 1 d . . . C16 C 0.61528(16) 0.54332(11) 0.24184(13) 0.0368(4) Uani 1 1 d . . . H16 H 0.5999 0.5942 0.1950 0.044 Uiso 1 1 calc R . . C17 C 0.56857(17) 0.54996(13) 0.31707(15) 0.0446(4) Uani 1 1 d . . . H17 H 0.5221 0.6053 0.3217 0.054 Uiso 1 1 calc R . . C18 C 0.58936(17) 0.47618(13) 0.38555(15) 0.0439(4) Uani 1 1 d . . . H18 H 0.5574 0.4807 0.4372 0.053 Uiso 1 1 calc R . . C19 C 0.65700(16) 0.39598(13) 0.37808(13) 0.0400(4) Uani 1 1 d . . . H19 H 0.6711 0.3449 0.4245 0.048 Uiso 1 1 calc R . . C20 C 0.70409(15) 0.38978(11) 0.30349(12) 0.0323(3) Uani 1 1 d . . . H20 H 0.7509 0.3344 0.2994 0.039 Uiso 1 1 calc R . . C21 C 0.77081(12) 0.89827(9) 0.23516(10) 0.0199(3) Uani 1 1 d . . . C22 C 0.69976(12) 0.90335(9) 0.29721(10) 0.0212(3) Uani 1 1 d . . . C23 C 0.66816(12) 0.99541(10) 0.32476(10) 0.0222(3) Uani 1 1 d . . . H23 H 0.6223 0.9984 0.3672 0.027 Uiso 1 1 calc R . . C24 C 0.70266(13) 1.08315(10) 0.29104(11) 0.0263(3) Uani 1 1 d . . . H24 H 0.6799 1.1455 0.3098 0.032 Uiso 1 1 calc R . . C25 C 0.77015(13) 1.07851(10) 0.23021(10) 0.0257(3) Uani 1 1 d . . . H25 H 0.7938 1.1385 0.2075 0.031 Uiso 1 1 calc R . . C26 C 0.80474(12) 0.98805(10) 0.20098(10) 0.0218(3) Uani 1 1 d . . . C27 C 0.65660(15) 0.80583(10) 0.32661(11) 0.0281(3) Uani 1 1 d . . . H27A H 0.5926 0.7724 0.2656 0.034 Uiso 1 1 calc R . . H27B H 0.7287 0.7628 0.3498 0.034 Uiso 1 1 calc R . . C28 C 0.60281(14) 0.81190(10) 0.40668(11) 0.0246(3) Uani 1 1 d . . . C29 C 0.67695(15) 0.79634(12) 0.50601(12) 0.0325(3) Uani 1 1 d . . . H29 H 0.7626 0.7833 0.5234 0.039 Uiso 1 1 calc R . . C30 C 0.62796(18) 0.79955(13) 0.58006(13) 0.0425(4) Uani 1 1 d . . . H30 H 0.6800 0.7887 0.6476 0.051 Uiso 1 1 calc R . . C31 C 0.50381(18) 0.81851(12) 0.55587(14) 0.0418(4) Uani 1 1 d . . . H31 H 0.4704 0.8218 0.6068 0.050 Uiso 1 1 calc R . . C32 C 0.42842(17) 0.83271(13) 0.45738(15) 0.0427(4) Uani 1 1 d . . . H32 H 0.3425 0.8448 0.4402 0.051 Uiso 1 1 calc R . . C33 C 0.47757(15) 0.82946(12) 0.38319(13) 0.0339(4) Uani 1 1 d . . . H33 H 0.4249 0.8393 0.3156 0.041 Uiso 1 1 calc R . . C34 C 0.87779(13) 0.98431(10) 0.13397(10) 0.0250(3) Uani 1 1 d . . . H34A H 0.9348 0.9289 0.1537 0.030 Uiso 1 1 calc R . . H34B H 0.9303 1.0468 0.1460 0.030 Uiso 1 1 calc R . . C35 C 0.79934(13) 0.97069(9) 0.02208(10) 0.0228(3) Uani 1 1 d . . . C36 C 0.84859(14) 0.92605(10) -0.04252(11) 0.0276(3) Uani 1 1 d . . . H36 H 0.9292 0.8999 -0.0158 0.033 Uiso 1 1 calc R . . C37 C 0.78093(15) 0.91928(11) -0.14590(11) 0.0319(3) Uani 1 1 d . . . H37 H 0.8159 0.8893 -0.1892 0.038 Uiso 1 1 calc R . . C38 C 0.66274(15) 0.95617(11) -0.18568(11) 0.0328(4) Uani 1 1 d . . . H38 H 0.6170 0.9523 -0.2562 0.039 Uiso 1 1 calc R . . C39 C 0.61181(14) 0.99850(11) -0.12252(11) 0.0300(3) Uani 1 1 d . . . H39 H 0.5302 1.0228 -0.1496 0.036 Uiso 1 1 calc R . . C40 C 0.67926(13) 1.00589(10) -0.01911(11) 0.0250(3) Uani 1 1 d . . . H40 H 0.6432 1.0352 0.0237 0.030 Uiso 1 1 calc R . . C41 C 0.94534(17) 0.60967(11) 0.46944(12) 0.0352(4) Uani 1 1 d . . . H41A H 1.0271 0.5823 0.4823 0.053 Uiso 1 1 calc R . . H41B H 0.8807 0.5705 0.4144 0.053 Uiso 1 1 calc R . . H41C H 0.9265 0.6069 0.5302 0.053 Uiso 1 1 calc R . . C42 C 1.03614(15) 0.77308(10) 0.52153(11) 0.0287(3) Uani 1 1 d . . . H42A H 1.1204 0.7464 0.5425 0.034 Uiso 1 1 calc R . . H42B H 1.0116 0.7761 0.5803 0.034 Uiso 1 1 calc R . . C43 C 1.03689(14) 0.87464(10) 0.48219(10) 0.0268(3) Uani 1 1 d . . . H43A H 0.9521 0.9006 0.4599 0.032 Uiso 1 1 calc R . . H43B H 1.0952 0.9210 0.5355 0.032 Uiso 1 1 calc R . . C44 C 1.11188(15) 0.96135(10) 0.37478(12) 0.0325(3) Uani 1 1 d . . . H44A H 1.0394 1.0029 0.3533 0.049 Uiso 1 1 calc R . . H44B H 1.1424 0.9531 0.3203 0.049 Uiso 1 1 calc R . . H44C H 1.1784 0.9934 0.4340 0.049 Uiso 1 1 calc R . . C45 C 0.52279(14) 0.77277(11) 0.03217(12) 0.0323(3) Uani 1 1 d . . . H45A H 0.5578 0.8404 0.0330 0.048 Uiso 1 1 calc R . . H45B H 0.5144 0.7622 0.0964 0.048 Uiso 1 1 calc R . . H45C H 0.4404 0.7641 -0.0226 0.048 Uiso 1 1 calc R . . C46 C 0.61054(14) 0.71151(11) -0.07953(11) 0.0285(3) Uani 1 1 d . . . H46A H 0.6372 0.7805 -0.0871 0.034 Uiso 1 1 calc R . . H46B H 0.5276 0.6949 -0.1332 0.034 Uiso 1 1 calc R . . C47 C 0.70417(14) 0.64026(11) -0.08653(11) 0.0295(3) Uani 1 1 d . . . H47A H 0.6746 0.5709 -0.0838 0.035 Uiso 1 1 calc R . . H47B H 0.7162 0.6469 -0.1506 0.035 Uiso 1 1 calc R . . C48 C 0.91564(14) 0.60113(11) -0.00352(11) 0.0299(3) Uani 1 1 d . . . H48A H 0.8909 0.5319 0.0023 0.045 Uiso 1 1 calc R . . H48B H 0.9931 0.6211 0.0535 0.045 Uiso 1 1 calc R . . H48C H 0.9293 0.6072 -0.0663 0.045 Uiso 1 1 calc R . . Li1 Li 0.9315(2) 0.74323(17) 0.30592(18) 0.0271(5) Uani 1 1 d . . . Li2 Li 0.7919(2) 0.70277(17) 0.12301(18) 0.0270(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0280(5) 0.0198(4) 0.0223(5) 0.0011(4) 0.0084(4) 0.0041(4) O2 0.0271(5) 0.0226(5) 0.0213(5) 0.0009(4) 0.0086(4) 0.0068(4) O3 0.0368(6) 0.0217(5) 0.0206(5) 0.0007(4) 0.0056(4) 0.0011(4) O4 0.0339(6) 0.0240(5) 0.0249(5) -0.0020(4) 0.0102(5) 0.0019(4) O5 0.0270(5) 0.0294(5) 0.0253(5) 0.0025(4) 0.0097(4) 0.0045(4) O6 0.0243(5) 0.0291(5) 0.0230(5) -0.0029(4) 0.0048(4) 0.0058(4) C1 0.0318(8) 0.0204(6) 0.0169(6) 0.0025(5) 0.0114(6) 0.0043(5) C2 0.0335(8) 0.0256(7) 0.0192(7) 0.0036(5) 0.0138(6) 0.0073(6) C3 0.0400(9) 0.0325(8) 0.0288(8) 0.0098(6) 0.0192(7) 0.0139(7) C4 0.0565(11) 0.0223(7) 0.0407(9) 0.0090(6) 0.0295(9) 0.0124(7) C5 0.0562(11) 0.0192(7) 0.0337(8) 0.0004(6) 0.0248(8) -0.0016(6) C6 0.0390(9) 0.0234(7) 0.0204(7) 0.0017(5) 0.0141(6) -0.0005(6) C7 0.0255(7) 0.0313(7) 0.0196(7) -0.0006(5) 0.0058(6) 0.0068(6) C8 0.0184(7) 0.0253(7) 0.0227(7) -0.0047(5) 0.0054(6) -0.0009(5) C9 0.0233(7) 0.0257(7) 0.0313(8) -0.0028(6) 0.0110(6) 0.0016(5) C10 0.0245(8) 0.0265(7) 0.0349(8) 0.0033(6) 0.0090(7) -0.0008(6) C11 0.0345(9) 0.0320(8) 0.0340(8) 0.0000(6) 0.0178(7) -0.0069(6) C12 0.0431(10) 0.0302(8) 0.0455(10) -0.0045(7) 0.0300(8) -0.0009(7) C13 0.0300(8) 0.0244(7) 0.0362(8) -0.0019(6) 0.0168(7) 0.0016(6) C14 0.0381(9) 0.0263(7) 0.0225(7) 0.0009(5) 0.0052(7) -0.0087(6) C15 0.0237(7) 0.0259(7) 0.0258(7) 0.0021(5) 0.0024(6) -0.0068(5) C16 0.0370(9) 0.0282(8) 0.0429(10) 0.0073(6) 0.0126(8) -0.0013(6) C17 0.0394(10) 0.0362(9) 0.0606(12) 0.0013(8) 0.0217(9) 0.0023(7) C18 0.0376(10) 0.0505(10) 0.0485(11) 0.0024(8) 0.0223(8) -0.0022(8) C19 0.0383(10) 0.0437(9) 0.0404(10) 0.0129(7) 0.0170(8) 0.0017(7) C20 0.0317(8) 0.0308(8) 0.0322(8) 0.0068(6) 0.0092(7) 0.0017(6) C21 0.0177(6) 0.0210(6) 0.0162(6) -0.0003(5) 0.0012(5) 0.0031(5) C22 0.0189(7) 0.0233(6) 0.0172(6) 0.0004(5) 0.0021(5) 0.0019(5) C23 0.0174(7) 0.0267(7) 0.0192(7) -0.0018(5) 0.0033(5) 0.0022(5) C24 0.0245(7) 0.0212(6) 0.0284(8) -0.0038(5) 0.0049(6) 0.0026(5) C25 0.0257(7) 0.0209(6) 0.0246(7) 0.0025(5) 0.0032(6) -0.0023(5) C26 0.0159(6) 0.0263(7) 0.0188(7) 0.0013(5) 0.0016(5) 0.0011(5) C27 0.0337(8) 0.0262(7) 0.0263(8) -0.0010(5) 0.0138(7) -0.0005(6) C28 0.0267(7) 0.0218(6) 0.0262(7) -0.0004(5) 0.0113(6) -0.0007(5) C29 0.0256(8) 0.0427(9) 0.0276(8) 0.0000(6) 0.0083(6) 0.0043(6) C30 0.0471(11) 0.0543(10) 0.0260(8) -0.0038(7) 0.0143(8) -0.0008(8) C31 0.0502(11) 0.0427(9) 0.0459(10) -0.0077(7) 0.0350(9) -0.0062(8) C32 0.0306(9) 0.0448(10) 0.0591(12) -0.0018(8) 0.0246(9) 0.0016(7) C33 0.0251(8) 0.0388(8) 0.0358(9) 0.0041(6) 0.0091(7) 0.0026(6) C34 0.0205(7) 0.0294(7) 0.0228(7) 0.0033(5) 0.0057(6) -0.0004(5) C35 0.0223(7) 0.0211(6) 0.0230(7) 0.0041(5) 0.0064(6) -0.0022(5) C36 0.0227(7) 0.0281(7) 0.0302(8) 0.0008(6) 0.0082(6) -0.0004(6) C37 0.0351(9) 0.0344(8) 0.0259(8) -0.0039(6) 0.0120(7) -0.0027(6) C38 0.0365(9) 0.0334(8) 0.0215(7) 0.0010(6) 0.0034(7) -0.0022(6) C39 0.0266(8) 0.0292(7) 0.0270(8) 0.0033(6) 0.0018(6) 0.0023(6) C40 0.0250(7) 0.0243(6) 0.0233(7) 0.0026(5) 0.0065(6) 0.0010(5) C41 0.0512(10) 0.0242(7) 0.0308(8) 0.0048(6) 0.0162(8) -0.0014(7) C42 0.0335(8) 0.0285(7) 0.0188(7) -0.0013(5) 0.0041(6) 0.0027(6) C43 0.0295(8) 0.0248(7) 0.0219(7) -0.0049(5) 0.0054(6) 0.0025(6) C44 0.0358(9) 0.0264(7) 0.0296(8) -0.0008(6) 0.0067(7) -0.0019(6) C45 0.0244(8) 0.0359(8) 0.0364(9) 0.0001(6) 0.0113(7) 0.0051(6) C46 0.0253(8) 0.0336(8) 0.0224(7) 0.0023(6) 0.0042(6) 0.0025(6) C47 0.0273(8) 0.0351(8) 0.0212(7) -0.0045(6) 0.0040(6) 0.0007(6) C48 0.0274(8) 0.0360(8) 0.0280(8) -0.0005(6) 0.0123(6) 0.0081(6) Li1 0.0295(13) 0.0250(11) 0.0258(12) 0.0002(9) 0.0091(10) 0.0041(9) Li2 0.0265(13) 0.0289(12) 0.0225(12) -0.0008(9) 0.0059(10) 0.0024(9) _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 1.3177(15) . ? O1 Li1 1.869(2) . ? O1 Li2 1.938(2) . ? O2 C21 1.3211(15) . ? O2 Li2 1.872(2) . ? O2 Li1 1.876(2) . ? O3 C42 1.4263(17) . ? O3 C41 1.4342(16) . ? O3 Li1 1.965(3) . ? O4 C44 1.4277(18) . ? O4 C43 1.4335(17) . ? O4 Li1 2.301(3) . ? O5 C45 1.4235(16) . ? O5 C46 1.4329(17) . ? O5 Li2 2.130(3) . ? O6 C47 1.4244(17) . ? O6 C48 1.4332(16) . ? O6 Li2 2.017(3) . ? C1 C6 1.423(2) . ? C1 C2 1.422(2) . ? C2 C3 1.3949(18) . ? C2 C7 1.509(2) . ? C3 C4 1.386(2) . ? C4 C5 1.383(2) . ? C5 C6 1.3913(19) . ? C6 C14 1.513(2) . ? C7 C8 1.513(2) . ? C8 C9 1.3902(19) . ? C8 C13 1.3932(19) . ? C9 C10 1.388(2) . ? C10 C11 1.377(2) . ? C11 C12 1.389(2) . ? C12 C13 1.381(2) . ? C14 C15 1.513(2) . ? C15 C16 1.389(2) . ? C15 C20 1.400(2) . ? C16 C17 1.384(3) . ? C17 C18 1.385(3) . ? C18 C19 1.381(2) . ? C19 C20 1.378(2) . ? C21 C26 1.4167(19) . ? C21 C22 1.427(2) . ? C22 C23 1.3923(17) . ? C22 C27 1.5166(19) . ? C23 C24 1.393(2) . ? C24 C25 1.378(2) . ? C25 C26 1.3966(18) . ? C26 C34 1.505(2) . ? C27 C28 1.505(2) . ? C28 C33 1.388(2) . ? C28 C29 1.389(2) . ? C29 C30 1.385(2) . ? C30 C31 1.379(3) . ? C31 C32 1.379(3) . ? C32 C33 1.388(2) . ? C34 C35 1.5217(19) . ? C35 C36 1.394(2) . ? C35 C40 1.3953(19) . ? C36 C37 1.393(2) . ? C37 C38 1.385(2) . ? C38 C39 1.377(2) . ? C39 C40 1.393(2) . ? C42 C43 1.498(2) . ? C46 C47 1.502(2) . ? Li1 Li2 2.543(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 Li1 136.40(11) . . ? C1 O1 Li2 139.73(11) . . ? Li1 O1 Li2 83.79(10) . . ? C21 O2 Li2 153.35(11) . . ? C21 O2 Li1 121.18(11) . . ? Li2 O2 Li1 85.44(11) . . ? C42 O3 C41 112.14(11) . . ? C42 O3 Li1 115.50(12) . . ? C41 O3 Li1 120.91(11) . . ? C44 O4 C43 111.11(10) . . ? C44 O4 Li1 132.28(10) . . ? C43 O4 Li1 98.04(10) . . ? C45 O5 C46 110.57(11) . . ? C45 O5 Li2 118.90(11) . . ? C46 O5 Li2 106.54(11) . . ? C47 O6 C48 111.92(10) . . ? C47 O6 Li2 112.60(11) . . ? C48 O6 Li2 122.21(11) . . ? O1 C1 C6 121.19(13) . . ? O1 C1 C2 121.35(12) . . ? C6 C1 C2 117.45(12) . . ? C3 C2 C1 120.50(14) . . ? C3 C2 C7 119.88(13) . . ? C1 C2 C7 119.53(11) . . ? C4 C3 C2 121.34(15) . . ? C5 C4 C3 118.58(13) . . ? C4 C5 C6 122.09(15) . . ? C5 C6 C1 119.97(14) . . ? C5 C6 C14 120.35(14) . . ? C1 C6 C14 119.59(12) . . ? C2 C7 C8 111.64(11) . . ? C9 C8 C13 117.97(14) . . ? C9 C8 C7 122.52(12) . . ? C13 C8 C7 119.50(12) . . ? C10 C9 C8 121.22(13) . . ? C11 C10 C9 120.06(13) . . ? C10 C11 C12 119.50(15) . . ? C13 C12 C11 120.27(14) . . ? C12 C13 C8 120.97(13) . . ? C15 C14 C6 111.93(12) . . ? C16 C15 C20 117.68(15) . . ? C16 C15 C14 122.26(13) . . ? C20 C15 C14 120.05(13) . . ? C17 C16 C15 121.17(15) . . ? C18 C17 C16 120.23(16) . . ? C19 C18 C17 119.44(17) . . ? C20 C19 C18 120.26(16) . . ? C19 C20 C15 121.23(15) . . ? O2 C21 C26 121.08(12) . . ? O2 C21 C22 120.43(12) . . ? C26 C21 C22 118.49(11) . . ? C23 C22 C21 119.87(12) . . ? C23 C22 C27 122.60(13) . . ? C21 C22 C27 117.48(11) . . ? C24 C23 C22 121.04(13) . . ? C25 C24 C23 119.28(12) . . ? C24 C25 C26 121.84(13) . . ? C25 C26 C21 119.47(13) . . ? C25 C26 C34 121.13(13) . . ? C21 C26 C34 119.40(11) . . ? C28 C27 C22 116.79(11) . . ? C33 C28 C29 118.22(14) . . ? C33 C28 C27 121.29(13) . . ? C29 C28 C27 120.44(13) . . ? C30 C29 C28 121.04(15) . . ? C31 C30 C29 120.10(16) . . ? C30 C31 C32 119.62(16) . . ? C31 C32 C33 120.24(16) . . ? C32 C33 C28 120.76(15) . . ? C26 C34 C35 115.29(12) . . ? C36 C35 C40 118.33(13) . . ? C36 C35 C34 120.26(12) . . ? C40 C35 C34 121.35(12) . . ? C35 C36 C37 120.78(14) . . ? C38 C37 C36 120.12(14) . . ? C39 C38 C37 119.71(14) . . ? C38 C39 C40 120.43(14) . . ? C35 C40 C39 120.61(14) . . ? O3 C42 C43 107.23(11) . . ? O4 C43 C42 107.71(11) . . ? O5 C46 C47 107.23(11) . . ? O6 C47 C46 107.20(11) . . ? O1 Li1 O2 96.13(12) . . ? O1 Li1 O3 110.27(12) . . ? O2 Li1 O3 128.11(14) . . ? O1 Li1 O4 143.99(14) . . ? O2 Li1 O4 104.59(11) . . ? O3 Li1 O4 79.42(9) . . ? O1 Li1 Li2 49.27(8) . . ? O2 Li1 Li2 47.21(8) . . ? O3 Li1 Li2 140.94(14) . . ? O4 Li1 Li2 138.15(13) . . ? O2 Li2 O1 93.96(11) . . ? O2 Li2 O6 142.15(15) . . ? O1 Li2 O6 104.62(11) . . ? O2 Li2 O5 103.70(11) . . ? O1 Li2 O5 143.70(14) . . ? O6 Li2 O5 80.35(9) . . ? O2 Li2 Li1 47.36(8) . . ? O1 Li2 Li1 46.94(8) . . ? O6 Li2 Li1 135.90(13) . . ? O5 Li2 Li1 143.50(13) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.319 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.053 _chemical_compound_source DME #===END data_COMPOUND_3 _database_code_depnum_ccdc_archive 'CCDC 299153' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point '> 633' _chemical_formula_moiety 'C44 H42 Li2 O6' _chemical_formula_sum 'C44 H42 Li2 O6' _chemical_formula_weight 680.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.015(3) _cell_length_b 11.345(2) _cell_length_c 15.006(2) _cell_angle_alpha 90.582(8) _cell_angle_beta 105.252(9) _cell_angle_gamma 95.986(11) _cell_volume 1797.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'cubic ' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27121 _diffrn_reflns_av_R_equivalents 0.1266 _diffrn_reflns_av_sigmaI/netI 0.1344 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.73 _reflns_number_total 8400 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.1241P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8400 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1473 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1855 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 0.797 _refine_ls_restrained_S_all 0.797 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.68863(15) 0.26774(15) 0.17914(10) 0.0239(4) Uani 1 1 d . . . O2 O 0.45363(17) 0.21769(19) 0.25963(12) 0.0377(5) Uani 1 1 d . . . O3 O 0.96828(16) 0.25536(17) 0.28291(11) 0.0287(4) Uani 1 1 d . . . O4 O 0.73384(15) 0.22600(15) 0.36653(10) 0.0222(4) Uani 1 1 d . . . O5 O 0.59961(16) 0.00176(15) 0.21806(10) 0.0269(4) Uani 1 1 d . . . O6 O 0.83456(16) 0.49540(15) 0.30862(11) 0.0263(4) Uani 1 1 d . . . C1 C 0.6617(2) 0.2815(2) 0.08918(15) 0.0193(5) Uani 1 1 d . . . C2 C 0.5465(2) 0.3242(2) 0.04141(16) 0.0226(5) Uani 1 1 d . . . C3 C 0.5216(2) 0.3405(2) -0.05270(17) 0.0281(6) Uani 1 1 d . . . H3 H 0.4462 0.3726 -0.0837 0.034 Uiso 1 1 calc R . . C4 C 0.6042(3) 0.3111(2) -0.10259(17) 0.0311(6) Uani 1 1 d . . . H4 H 0.5851 0.3220 -0.1673 0.037 Uiso 1 1 calc R . . C5 C 0.7150(2) 0.2657(2) -0.05715(16) 0.0271(6) Uani 1 1 d . . . H5 H 0.7709 0.2440 -0.0916 0.033 Uiso 1 1 calc R . . C6 C 0.7461(2) 0.2512(2) 0.03798(15) 0.0215(5) Uani 1 1 d . . . C7 C 0.4520(2) 0.3514(2) 0.09420(17) 0.0273(6) Uani 1 1 d . . . H7A H 0.4054 0.4168 0.0643 0.033 Uiso 1 1 calc R . . H7B H 0.4989 0.3794 0.1579 0.033 Uiso 1 1 calc R . . C8 C 0.3570(2) 0.2462(2) 0.09922(16) 0.0236(5) Uani 1 1 d . . . C9 C 0.3556(2) 0.1876(2) 0.17999(17) 0.0273(6) Uani 1 1 d . . . C10 C 0.2663(3) 0.0934(3) 0.18311(19) 0.0348(7) Uani 1 1 d . . . H10 H 0.2679 0.0559 0.2397 0.042 Uiso 1 1 calc R . . C11 C 0.1749(3) 0.0546(3) 0.10345(19) 0.0363(7) Uani 1 1 d . . . H11 H 0.1133 -0.0101 0.1047 0.044 Uiso 1 1 calc R . . C12 C 0.1733(3) 0.1099(3) 0.02212(18) 0.0344(7) Uani 1 1 d . . . H12 H 0.1104 0.0835 -0.0329 0.041 Uiso 1 1 calc R . . C13 C 0.2635(2) 0.2041(2) 0.02030(18) 0.0299(6) Uani 1 1 d . . . H13 H 0.2613 0.2410 -0.0365 0.036 Uiso 1 1 calc R . . C14 C 0.4282(3) 0.2815(4) 0.3320(2) 0.0553(10) Uani 1 1 d . . . H14A H 0.4136 0.3624 0.3131 0.083 Uiso 1 1 calc R . . H14B H 0.5006 0.2843 0.3867 0.083 Uiso 1 1 calc R . . H14C H 0.3526 0.2423 0.3467 0.083 Uiso 1 1 calc R . . C15 C 0.8681(2) 0.2037(2) 0.08828(16) 0.0233(5) Uani 1 1 d . . . H15A H 0.8937 0.1517 0.0446 0.028 Uiso 1 1 calc R . . H15B H 0.8517 0.1540 0.1386 0.028 Uiso 1 1 calc R . . C16 C 0.9778(2) 0.2978(2) 0.12949(16) 0.0209(5) Uani 1 1 d . . . C17 C 1.0291(2) 0.3179(2) 0.22440(16) 0.0227(5) Uani 1 1 d . . . C18 C 1.1315(2) 0.4020(2) 0.26016(17) 0.0285(6) Uani 1 1 d . . . H18 H 1.1649 0.4138 0.3252 0.034 Uiso 1 1 calc R . . C19 C 1.1850(2) 0.4691(2) 0.20069(18) 0.0309(6) Uani 1 1 d . . . H19 H 1.2556 0.5266 0.2248 0.037 Uiso 1 1 calc R . . C20 C 1.1354(2) 0.4521(2) 0.10619(18) 0.0290(6) Uani 1 1 d . . . H20 H 1.1710 0.4984 0.0651 0.035 Uiso 1 1 calc R . . C21 C 1.0337(2) 0.3674(2) 0.07192(17) 0.0262(6) Uani 1 1 d . . . H21 H 1.0008 0.3562 0.0069 0.031 Uiso 1 1 calc R . . C22 C 1.0451(3) 0.2046(3) 0.36172(19) 0.0409(7) Uani 1 1 d . . . H22A H 1.1036 0.1570 0.3422 0.061 Uiso 1 1 calc R . . H22B H 0.9910 0.1540 0.3916 0.061 Uiso 1 1 calc R . . H22C H 1.0936 0.2681 0.4055 0.061 Uiso 1 1 calc R . . C23 C 0.7378(2) 0.2096(2) 0.45423(15) 0.0201(5) Uani 1 1 d . . . C24 C 0.6888(2) 0.1005(2) 0.48262(16) 0.0226(5) Uani 1 1 d . . . C25 C 0.6909(2) 0.0871(2) 0.57490(16) 0.0269(6) Uani 1 1 d . . . H25 H 0.6567 0.0139 0.5934 0.032 Uiso 1 1 calc R . . C26 C 0.7420(2) 0.1784(2) 0.64088(17) 0.0291(6) Uani 1 1 d . . . H26 H 0.7417 0.1685 0.7036 0.035 Uiso 1 1 calc R . . C27 C 0.7934(2) 0.2843(2) 0.61322(16) 0.0269(6) Uani 1 1 d . . . H27 H 0.8300 0.3464 0.6582 0.032 Uiso 1 1 calc R . . C28 C 0.7926(2) 0.3019(2) 0.52151(15) 0.0219(5) Uani 1 1 d . . . C29 C 0.6346(2) 0.0002(2) 0.41153(16) 0.0250(6) Uani 1 1 d . . . H29A H 0.5625 0.0261 0.3641 0.030 Uiso 1 1 calc R . . H29B H 0.6017 -0.0681 0.4421 0.030 Uiso 1 1 calc R . . C30 C 0.7303(2) -0.0398(2) 0.36420(16) 0.0225(5) Uani 1 1 d . . . C31 C 0.7106(2) -0.0411(2) 0.26823(16) 0.0244(6) Uani 1 1 d . . . C32 C 0.7986(3) -0.0798(2) 0.22635(18) 0.0292(6) Uani 1 1 d . . . H32 H 0.7831 -0.0812 0.1610 0.035 Uiso 1 1 calc R . . C33 C 0.9098(3) -0.1166(2) 0.28151(19) 0.0346(7) Uani 1 1 d . . . H33 H 0.9710 -0.1419 0.2535 0.041 Uiso 1 1 calc R . . C34 C 0.9320(3) -0.1165(3) 0.37660(19) 0.0347(7) Uani 1 1 d . . . H34 H 1.0074 -0.1426 0.4140 0.042 Uiso 1 1 calc R . . C35 C 0.8422(2) -0.0778(2) 0.41625(17) 0.0296(6) Uani 1 1 d . . . H35 H 0.8579 -0.0771 0.4816 0.035 Uiso 1 1 calc R . . C36 C 0.5640(3) -0.0167(2) 0.11881(16) 0.0304(6) Uani 1 1 d . . . H36A H 0.6251 0.0306 0.0928 0.046 Uiso 1 1 calc R . . H36B H 0.4794 0.0076 0.0931 0.046 Uiso 1 1 calc R . . H36C H 0.5634 -0.1009 0.1032 0.046 Uiso 1 1 calc R . . C37 C 0.8503(2) 0.4163(2) 0.49196(16) 0.0241(6) Uani 1 1 d . . . H37A H 0.9037 0.3970 0.4512 0.029 Uiso 1 1 calc R . . H37B H 0.9066 0.4599 0.5475 0.029 Uiso 1 1 calc R . . C38 C 0.7556(2) 0.4978(2) 0.44140(15) 0.0225(5) Uani 1 1 d . . . C39 C 0.7516(2) 0.5392(2) 0.35328(16) 0.0232(5) Uani 1 1 d . . . C40 C 0.6681(3) 0.6185(2) 0.31288(17) 0.0285(6) Uani 1 1 d . . . H40 H 0.6670 0.6459 0.2531 0.034 Uiso 1 1 calc R . . C41 C 0.5859(3) 0.6580(2) 0.35946(17) 0.0297(6) Uani 1 1 d . . . H41 H 0.5299 0.7137 0.3320 0.036 Uiso 1 1 calc R . . C42 C 0.5848(2) 0.6169(2) 0.44532(17) 0.0295(6) Uani 1 1 d . . . H42 H 0.5274 0.6425 0.4769 0.035 Uiso 1 1 calc R . . C43 C 0.6696(2) 0.5372(2) 0.48483(16) 0.0270(6) Uani 1 1 d . . . H43 H 0.6685 0.5086 0.5439 0.032 Uiso 1 1 calc R . . C44 C 0.8426(3) 0.5487(2) 0.22378(18) 0.0339(7) Uani 1 1 d . . . H44A H 0.7623 0.5292 0.1766 0.051 Uiso 1 1 calc R . . H44B H 0.9111 0.5184 0.2030 0.051 Uiso 1 1 calc R . . H44C H 0.8600 0.6350 0.2338 0.051 Uiso 1 1 calc R . . Li1 Li 0.6160(4) 0.1754(4) 0.2564(3) 0.0265(9) Uani 1 1 d . . . Li2 Li 0.8087(4) 0.3137(4) 0.2882(3) 0.0275(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0243(9) 0.0281(10) 0.0183(8) 0.0003(7) 0.0041(7) 0.0031(8) O2 0.0244(10) 0.0617(15) 0.0254(9) -0.0087(9) 0.0037(7) 0.0056(9) O3 0.0235(9) 0.0405(12) 0.0221(9) 0.0092(8) 0.0054(7) 0.0044(8) O4 0.0237(9) 0.0234(10) 0.0184(8) 0.0012(7) 0.0054(7) -0.0018(7) O5 0.0302(10) 0.0265(10) 0.0211(9) -0.0015(7) 0.0015(7) 0.0036(8) O6 0.0330(10) 0.0230(10) 0.0258(9) 0.0019(7) 0.0119(7) 0.0055(8) C1 0.0236(13) 0.0136(12) 0.0182(12) 0.0007(9) 0.0034(9) -0.0040(10) C2 0.0232(13) 0.0127(13) 0.0280(13) -0.0011(10) 0.0020(10) -0.0035(10) C3 0.0270(14) 0.0221(14) 0.0290(14) 0.0082(11) -0.0016(11) -0.0028(11) C4 0.0330(15) 0.0326(16) 0.0208(13) 0.0052(11) -0.0002(11) -0.0091(13) C5 0.0321(15) 0.0259(15) 0.0215(12) -0.0021(10) 0.0095(10) -0.0103(12) C6 0.0231(13) 0.0159(13) 0.0236(12) 0.0005(9) 0.0055(10) -0.0038(10) C7 0.0214(13) 0.0202(14) 0.0358(14) -0.0034(11) -0.0002(10) 0.0033(11) C8 0.0206(13) 0.0199(14) 0.0300(13) -0.0044(10) 0.0048(10) 0.0065(10) C9 0.0192(13) 0.0342(16) 0.0284(13) -0.0068(11) 0.0054(10) 0.0059(11) C10 0.0281(15) 0.0376(17) 0.0413(16) 0.0012(13) 0.0143(12) 0.0017(13) C11 0.0297(15) 0.0334(17) 0.0477(17) -0.0090(13) 0.0168(13) -0.0038(13) C12 0.0268(15) 0.0376(18) 0.0358(15) -0.0140(13) 0.0057(12) -0.0016(13) C13 0.0267(14) 0.0320(16) 0.0294(14) -0.0054(11) 0.0040(11) 0.0048(12) C14 0.0316(17) 0.082(3) 0.0491(19) -0.0348(18) 0.0033(14) 0.0152(17) C15 0.0276(14) 0.0192(13) 0.0255(13) -0.0015(10) 0.0118(10) 0.0020(10) C16 0.0213(13) 0.0173(13) 0.0255(12) 0.0000(10) 0.0077(10) 0.0046(10) C17 0.0184(12) 0.0249(14) 0.0279(13) 0.0025(10) 0.0097(10) 0.0067(10) C18 0.0234(14) 0.0298(16) 0.0312(14) -0.0056(11) 0.0056(11) 0.0030(12) C19 0.0224(14) 0.0227(15) 0.0460(16) -0.0044(12) 0.0081(12) -0.0013(11) C20 0.0276(14) 0.0229(14) 0.0400(15) 0.0062(11) 0.0145(12) 0.0037(11) C21 0.0265(14) 0.0264(15) 0.0266(13) 0.0013(10) 0.0077(10) 0.0049(11) C22 0.0325(16) 0.0457(19) 0.0418(16) 0.0190(14) 0.0041(13) 0.0057(14) C23 0.0174(12) 0.0263(14) 0.0178(12) 0.0031(9) 0.0063(9) 0.0035(10) C24 0.0210(13) 0.0235(14) 0.0242(12) 0.0031(10) 0.0072(10) 0.0029(10) C25 0.0304(14) 0.0273(15) 0.0262(13) 0.0046(11) 0.0132(11) 0.0022(12) C26 0.0357(15) 0.0331(16) 0.0214(13) 0.0036(11) 0.0118(11) 0.0057(12) C27 0.0304(14) 0.0283(15) 0.0212(13) -0.0034(10) 0.0056(10) 0.0036(12) C28 0.0182(12) 0.0250(14) 0.0220(12) -0.0011(10) 0.0044(9) 0.0027(10) C29 0.0230(13) 0.0229(14) 0.0282(13) 0.0008(10) 0.0075(10) -0.0037(11) C30 0.0265(14) 0.0135(13) 0.0265(13) 0.0001(9) 0.0070(10) -0.0021(10) C31 0.0275(14) 0.0149(13) 0.0286(13) -0.0001(10) 0.0045(10) -0.0002(11) C32 0.0343(15) 0.0223(15) 0.0307(14) -0.0050(11) 0.0101(11) -0.0013(12) C33 0.0346(16) 0.0265(16) 0.0466(17) -0.0050(12) 0.0178(13) 0.0039(13) C34 0.0298(15) 0.0296(16) 0.0426(16) -0.0012(12) 0.0047(12) 0.0068(12) C35 0.0335(15) 0.0258(15) 0.0268(13) 0.0018(11) 0.0036(11) 0.0028(12) C36 0.0400(16) 0.0244(15) 0.0239(13) -0.0050(11) 0.0047(11) 0.0003(12) C37 0.0211(13) 0.0268(14) 0.0221(12) -0.0020(10) 0.0027(10) -0.0001(11) C38 0.0240(13) 0.0204(14) 0.0204(12) -0.0047(10) 0.0034(10) -0.0026(10) C39 0.0246(13) 0.0188(13) 0.0255(13) -0.0039(10) 0.0073(10) -0.0020(11) C40 0.0358(15) 0.0246(15) 0.0247(13) -0.0004(10) 0.0066(11) 0.0053(12) C41 0.0303(15) 0.0268(15) 0.0301(14) -0.0037(11) 0.0033(11) 0.0075(12) C42 0.0267(14) 0.0324(16) 0.0289(14) -0.0082(11) 0.0064(11) 0.0036(12) C43 0.0293(14) 0.0282(15) 0.0209(12) -0.0058(10) 0.0045(10) -0.0023(12) C44 0.0498(18) 0.0263(16) 0.0340(15) 0.0105(12) 0.0222(13) 0.0122(13) Li1 0.025(2) 0.029(2) 0.026(2) -0.0009(18) 0.0073(17) 0.0023(19) Li2 0.027(2) 0.032(3) 0.024(2) 0.0011(17) 0.0083(17) -0.0002(19) _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 1.318(3) . ? O1 Li1 1.850(4) . ? O1 Li2 1.844(4) . ? O2 C9 1.395(3) . ? O2 C14 1.403(3) . ? O2 Li1 1.911(5) . ? O3 C17 1.395(3) . ? O3 C22 1.427(3) . ? O3 Li2 1.962(5) . ? O4 C23 1.321(3) . ? O4 Li2 1.847(4) . ? O4 Li1 1.855(4) . ? O5 C31 1.394(3) . ? O5 C36 1.444(3) . ? O5 Li1 2.023(5) . ? O6 C39 1.393(3) . ? O6 C44 1.435(3) . ? O6 Li2 2.060(5) . ? C1 C6 1.418(3) . ? C1 C2 1.420(3) . ? C2 C3 1.384(3) . ? C2 C7 1.517(3) . ? C3 C4 1.384(4) . ? C4 C5 1.386(4) . ? C5 C6 1.393(3) . ? C6 C15 1.514(3) . ? C7 C8 1.520(4) . ? C8 C13 1.391(3) . ? C8 C9 1.391(4) . ? C9 C10 1.385(4) . ? C10 C11 1.378(4) . ? C11 C12 1.375(4) . ? C12 C13 1.387(4) . ? C15 C16 1.519(3) . ? C16 C21 1.393(3) . ? C16 C17 1.394(3) . ? C17 C18 1.385(3) . ? C18 C19 1.385(4) . ? C19 C20 1.383(4) . ? C20 C21 1.379(4) . ? C23 C24 1.413(3) . ? C23 C28 1.417(3) . ? C24 C25 1.389(3) . ? C24 C29 1.512(3) . ? C25 C26 1.391(4) . ? C26 C27 1.388(4) . ? C27 C28 1.391(3) . ? C28 C37 1.507(3) . ? C29 C30 1.520(3) . ? C30 C35 1.388(4) . ? C30 C31 1.398(3) . ? C31 C32 1.390(4) . ? C31 Li1 2.756(5) . ? C32 C33 1.392(4) . ? C33 C34 1.383(4) . ? C34 C35 1.385(4) . ? C37 C38 1.523(3) . ? C38 C43 1.389(3) . ? C38 C39 1.399(3) . ? C39 C40 1.384(4) . ? C40 C41 1.386(4) . ? C41 C42 1.377(4) . ? C42 C43 1.392(4) . ? Li1 Li2 2.440(6) . ? 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 Li1 134.86(19) . . ? C1 O1 Li2 142.4(2) . . ? Li1 O1 Li2 82.68(19) . . ? C9 O2 C14 118.6(2) . . ? C9 O2 Li1 115.73(18) . . ? C14 O2 Li1 125.5(2) . . ? C17 O3 C22 117.81(19) . . ? C17 O3 Li2 113.91(19) . . ? C22 O3 Li2 120.4(2) . . ? C23 O4 Li2 143.90(19) . . ? C23 O4 Li1 133.08(19) . . ? Li2 O4 Li1 82.44(19) . . ? C31 O5 C36 117.86(19) . . ? C31 O5 Li1 106.02(18) . . ? C36 O5 Li1 112.04(18) . . ? C39 O6 C44 116.77(19) . . ? C39 O6 Li2 113.80(18) . . ? C44 O6 Li2 108.93(18) . . ? O1 C1 C6 120.5(2) . . ? O1 C1 C2 120.8(2) . . ? C6 C1 C2 118.7(2) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 C7 120.8(2) . . ? C1 C2 C7 119.5(2) . . ? C4 C3 C2 121.5(2) . . ? C3 C4 C5 119.3(2) . . ? C4 C5 C6 121.3(2) . . ? C5 C6 C1 119.4(2) . . ? C5 C6 C15 121.6(2) . . ? C1 C6 C15 119.0(2) . . ? C2 C7 C8 113.9(2) . . ? C13 C8 C9 116.2(2) . . ? C13 C8 C7 120.1(2) . . ? C9 C8 C7 123.8(2) . . ? C10 C9 C8 122.6(2) . . ? C10 C9 O2 118.0(2) . . ? C8 C9 O2 119.2(2) . . ? C9 C10 C11 119.4(3) . . ? C12 C11 C10 119.7(3) . . ? C11 C12 C13 120.1(2) . . ? C12 C13 C8 122.0(3) . . ? C6 C15 C16 114.9(2) . . ? C21 C16 C17 116.8(2) . . ? C21 C16 C15 120.2(2) . . ? C17 C16 C15 123.0(2) . . ? C18 C17 O3 120.6(2) . . ? C18 C17 C16 121.8(2) . . ? O3 C17 C16 117.5(2) . . ? C17 C18 C19 119.7(2) . . ? C20 C19 C18 119.8(2) . . ? C19 C20 C21 119.6(2) . . ? C20 C21 C16 122.2(2) . . ? O4 C23 C24 121.0(2) . . ? O4 C23 C28 119.9(2) . . ? C24 C23 C28 119.0(2) . . ? C25 C24 C23 119.7(2) . . ? C25 C24 C29 121.1(2) . . ? C23 C24 C29 119.2(2) . . ? C26 C25 C24 121.5(2) . . ? C27 C26 C25 118.7(2) . . ? C26 C27 C28 121.8(2) . . ? C27 C28 C23 119.3(2) . . ? C27 C28 C37 121.7(2) . . ? C23 C28 C37 119.0(2) . . ? C24 C29 C30 113.4(2) . . ? C35 C30 C31 117.3(2) . . ? C35 C30 C29 120.2(2) . . ? C31 C30 C29 122.5(2) . . ? C32 C31 O5 122.5(2) . . ? C32 C31 C30 121.5(2) . . ? O5 C31 C30 116.0(2) . . ? C32 C31 Li1 128.5(2) . . ? O5 C31 Li1 44.88(13) . . ? C30 C31 Li1 91.97(17) . . ? C31 C32 C33 119.1(2) . . ? C34 C33 C32 120.7(3) . . ? C33 C34 C35 118.8(3) . . ? C34 C35 C30 122.6(2) . . ? C28 C37 C38 115.0(2) . . ? C43 C38 C39 116.9(2) . . ? C43 C38 C37 119.3(2) . . ? C39 C38 C37 123.7(2) . . ? C40 C39 O6 122.3(2) . . ? C40 C39 C38 121.2(2) . . ? O6 C39 C38 116.6(2) . . ? C41 C40 C39 120.1(2) . . ? C42 C41 C40 120.4(2) . . ? C41 C42 C43 118.6(2) . . ? C38 C43 C42 122.7(2) . . ? O1 Li1 O4 97.2(2) . . ? O1 Li1 O2 113.0(2) . . ? O4 Li1 O2 109.3(2) . . ? O1 Li1 O5 110.4(2) . . ? O4 Li1 O5 117.4(2) . . ? O2 Li1 O5 109.2(2) . . ? O1 Li1 Li2 48.56(14) . . ? O4 Li1 Li2 48.64(14) . . ? O2 Li1 Li2 124.5(2) . . ? O5 Li1 Li2 126.3(2) . . ? O1 Li1 C31 108.33(19) . . ? O4 Li1 C31 89.63(17) . . ? O2 Li1 C31 131.2(2) . . ? O5 Li1 C31 29.10(9) . . ? Li2 Li1 C31 102.06(18) . . ? O1 Li2 O4 97.6(2) . . ? O1 Li2 O3 108.1(2) . . ? O4 Li2 O3 111.2(2) . . ? O1 Li2 O6 111.4(2) . . ? O4 Li2 O6 117.6(2) . . ? O3 Li2 O6 109.9(2) . . ? O1 Li2 Li1 48.76(14) . . ? O4 Li2 Li1 48.92(14) . . ? O3 Li2 Li1 119.3(2) . . ? O6 Li2 Li1 130.5(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.277 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.057 _chemical_compound_source Et2O #===END data_COMPOUND_4 _database_code_depnum_ccdc_archive 'CCDC 299154' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 355 _chemical_formula_moiety 'C52 H62 Li2 O10' _chemical_formula_sum 'C52 H62 Li2 O10' _chemical_formula_weight 860.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6584(13) _cell_length_b 10.738(2) _cell_length_c 12.246(2) _cell_angle_alpha 97.659(9) _cell_angle_beta 112.495(9) _cell_angle_gamma 94.353(13) _cell_volume 1151.7(4) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9834 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16328 _diffrn_reflns_av_R_equivalents 0.2389 _diffrn_reflns_av_sigmaI/netI 0.2203 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 27.94 _reflns_number_total 5327 _reflns_number_gt 1988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0986P)^2^+0.3450P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5327 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2644 _refine_ls_R_factor_gt 0.0965 _refine_ls_wR_factor_ref 0.2690 _refine_ls_wR_factor_gt 0.1970 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1223(3) 0.0958(3) 0.0554(3) 0.0284(8) Uani 1 1 d . . . O2 O -0.0080(4) 0.4556(3) -0.1551(3) 0.0477(10) Uani 1 1 d . . . O3 O 0.4904(4) 0.3111(3) 0.4987(3) 0.0520(10) Uani 1 1 d . . . O4 O -0.2720(4) 0.1705(3) -0.0547(3) 0.0400(9) Uani 1 1 d . . . O5 O -0.1419(4) 0.1059(3) 0.1653(3) 0.0420(9) Uani 1 1 d . . . C1 C 0.2381(5) 0.1868(4) 0.0828(4) 0.0253(10) Uani 1 1 d . . . C2 C 0.2425(5) 0.2618(4) -0.0037(4) 0.0275(11) Uani 1 1 d . . . C3 C 0.3603(5) 0.3580(4) 0.0274(4) 0.0280(11) Uani 1 1 d . . . H3 H 0.3628 0.4075 -0.0308 0.034 Uiso 1 1 calc R . . C4 C 0.4754(5) 0.3845(4) 0.1412(4) 0.0277(11) Uani 1 1 d . . . H4 H 0.5547 0.4526 0.1616 0.033 Uiso 1 1 calc R . . C5 C 0.4732(5) 0.3104(4) 0.2247(4) 0.0286(11) Uani 1 1 d . . . H5 H 0.5524 0.3278 0.3026 0.034 Uiso 1 1 calc R . . C6 C 0.3572(5) 0.2103(4) 0.1975(4) 0.0262(10) Uani 1 1 d . . . C7 C 0.1135(6) 0.2304(4) -0.1265(4) 0.0328(12) Uani 1 1 d . . . H7A H 0.1071 0.1398 -0.1593 0.039 Uiso 1 1 calc R . . H7B H 0.0178 0.2418 -0.1169 0.039 Uiso 1 1 calc R . . C8 C 0.1258(6) 0.3077(5) -0.2161(4) 0.0377(12) Uani 1 1 d . . . C9 C 0.0662(6) 0.4213(5) -0.2304(4) 0.0361(12) Uani 1 1 d . . . C10 C 0.0783(6) 0.4929(5) -0.3115(4) 0.0419(13) Uani 1 1 d . . . H10 H 0.0367 0.5703 -0.3182 0.050 Uiso 1 1 calc R . . C11 C 0.1543(7) 0.4498(6) -0.3856(5) 0.0545(17) Uani 1 1 d . . . H11 H 0.1644 0.4975 -0.4427 0.065 Uiso 1 1 calc R . . C12 C 0.2123(7) 0.3377(6) -0.3724(5) 0.0579(17) Uani 1 1 d . . . H12 H 0.2627 0.3072 -0.4217 0.070 Uiso 1 1 calc R . . C13 C 0.1994(6) 0.2689(5) -0.2902(5) 0.0492(15) Uani 1 1 d . . . H13 H 0.2420 0.1920 -0.2831 0.059 Uiso 1 1 calc R . . C14 C -0.0701(7) 0.5720(5) -0.1616(6) 0.0604(17) Uani 1 1 d . . . H14A H 0.0118 0.6430 -0.1359 0.091 Uiso 1 1 calc R . . H14B H -0.1251 0.5808 -0.1089 0.091 Uiso 1 1 calc R . . H14C H -0.1397 0.5721 -0.2445 0.091 Uiso 1 1 calc R . . C15 C 0.3516(5) 0.1318(4) 0.2904(4) 0.0348(12) Uani 1 1 d . . . H15A H 0.2874 0.1690 0.3292 0.042 Uiso 1 1 calc R . . H15B H 0.3012 0.0452 0.2482 0.042 Uiso 1 1 calc R . . C16 C 0.5022(6) 0.1210(4) 0.3878(4) 0.0317(11) Uani 1 1 d . . . C17 C 0.5725(6) 0.2163(5) 0.4921(4) 0.0355(12) Uani 1 1 d . . . C18 C 0.7127(6) 0.2087(5) 0.5770(5) 0.0467(14) Uani 1 1 d . . . H18 H 0.7595 0.2738 0.6455 0.056 Uiso 1 1 calc R . . C19 C 0.7856(7) 0.1057(5) 0.5625(5) 0.0497(15) Uani 1 1 d . . . H19 H 0.8833 0.1022 0.6212 0.060 Uiso 1 1 calc R . . C20 C 0.7224(7) 0.0099(5) 0.4674(5) 0.0495(15) Uani 1 1 d . . . H20 H 0.7726 -0.0616 0.4606 0.059 Uiso 1 1 calc R . . C21 C 0.5790(6) 0.0191(5) 0.3781(5) 0.0417(13) Uani 1 1 d . . . H21 H 0.5344 -0.0464 0.3097 0.050 Uiso 1 1 calc R . . C22 C 0.5582(8) 0.4106(6) 0.6015(5) 0.074(2) Uani 1 1 d . . . H22A H 0.5814 0.3745 0.6749 0.111 Uiso 1 1 calc R . . H22B H 0.4879 0.4725 0.5984 0.111 Uiso 1 1 calc R . . H22C H 0.6518 0.4528 0.6015 0.111 Uiso 1 1 calc R . . C23 C -0.2928(7) 0.2976(5) -0.0717(6) 0.0566(16) Uani 1 1 d . . . H23A H -0.3955 0.2987 -0.1305 0.085 Uiso 1 1 calc R . . H23B H -0.2192 0.3314 -0.1013 0.085 Uiso 1 1 calc R . . H23C H -0.2779 0.3500 0.0048 0.085 Uiso 1 1 calc R . . C24 C -0.3639(6) 0.1196(5) 0.0022(5) 0.0423(13) Uani 1 1 d . . . H24A H -0.3881 0.0265 -0.0243 0.051 Uiso 1 1 calc R . . H24B H -0.4602 0.1559 -0.0229 0.051 Uiso 1 1 calc R . . C25 C -0.2849(6) 0.1491(5) 0.1356(5) 0.0434(13) Uani 1 1 d . . . H25A H -0.2718 0.2416 0.1644 0.052 Uiso 1 1 calc R . . H25B H -0.3443 0.1054 0.1732 0.052 Uiso 1 1 calc R . . C26 C -0.0562(6) 0.1238(5) 0.2903(5) 0.0459(14) Uani 1 1 d . . . H26A H -0.0450 0.2134 0.3252 0.069 Uiso 1 1 calc R . . H26B H 0.0440 0.0985 0.3054 0.069 Uiso 1 1 calc R . . H26C H -0.1081 0.0718 0.3270 0.069 Uiso 1 1 calc R . . Li1 Li -0.0831(9) 0.0756(7) 0.0229(7) 0.0354(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0257(17) 0.0221(16) 0.0356(17) 0.0037(13) 0.0119(14) -0.0035(14) O2 0.058(3) 0.031(2) 0.059(2) 0.0018(17) 0.031(2) 0.0072(17) O3 0.065(3) 0.045(2) 0.043(2) -0.0048(17) 0.024(2) 0.003(2) O4 0.037(2) 0.0353(19) 0.053(2) 0.0077(16) 0.0234(17) 0.0052(16) O5 0.039(2) 0.048(2) 0.048(2) 0.0124(17) 0.0238(18) 0.0133(17) C1 0.028(3) 0.016(2) 0.031(2) 0.0001(18) 0.014(2) 0.0010(19) C2 0.028(3) 0.025(2) 0.028(2) 0.0012(19) 0.010(2) -0.001(2) C3 0.031(3) 0.020(2) 0.033(3) 0.0036(19) 0.014(2) 0.001(2) C4 0.028(3) 0.026(2) 0.029(2) 0.0013(19) 0.013(2) -0.002(2) C5 0.029(3) 0.024(2) 0.029(2) 0.0010(19) 0.010(2) 0.004(2) C6 0.028(3) 0.022(2) 0.029(2) -0.0003(19) 0.014(2) 0.000(2) C7 0.038(3) 0.025(2) 0.029(2) 0.005(2) 0.006(2) 0.005(2) C8 0.039(3) 0.035(3) 0.031(3) 0.001(2) 0.007(2) -0.002(2) C9 0.032(3) 0.033(3) 0.034(3) 0.002(2) 0.005(2) 0.000(2) C10 0.048(3) 0.038(3) 0.034(3) 0.010(2) 0.011(3) -0.002(2) C11 0.062(4) 0.062(4) 0.030(3) 0.016(3) 0.009(3) -0.014(3) C12 0.083(5) 0.047(4) 0.046(3) -0.002(3) 0.033(3) 0.001(3) C13 0.049(4) 0.052(4) 0.041(3) -0.001(3) 0.016(3) 0.003(3) C14 0.058(4) 0.030(3) 0.089(5) -0.001(3) 0.027(3) 0.010(3) C15 0.036(3) 0.033(3) 0.034(3) 0.006(2) 0.013(2) -0.002(2) C16 0.042(3) 0.034(3) 0.024(2) 0.012(2) 0.017(2) 0.002(2) C17 0.044(3) 0.034(3) 0.030(3) 0.007(2) 0.016(2) 0.003(2) C18 0.052(4) 0.045(3) 0.033(3) 0.008(2) 0.008(3) -0.006(3) C19 0.053(4) 0.047(3) 0.044(3) 0.011(3) 0.014(3) 0.002(3) C20 0.060(4) 0.053(3) 0.044(3) 0.021(3) 0.024(3) 0.011(3) C21 0.047(3) 0.040(3) 0.041(3) 0.014(2) 0.020(3) 0.001(3) C22 0.103(6) 0.057(4) 0.049(4) -0.019(3) 0.026(4) 0.006(4) C23 0.060(4) 0.047(3) 0.076(4) 0.033(3) 0.033(3) 0.021(3) C24 0.034(3) 0.039(3) 0.062(3) 0.006(3) 0.029(3) 0.001(2) C25 0.041(3) 0.043(3) 0.056(3) 0.007(3) 0.030(3) 0.009(3) C26 0.046(3) 0.042(3) 0.049(3) 0.008(3) 0.019(3) 0.006(3) Li1 0.030(5) 0.028(4) 0.041(5) 0.004(3) 0.009(4) -0.004(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 1.334(5) . ? O1 Li1 1.857(9) . ? O1 Li1 1.897(8) 2 ? O2 C9 1.399(6) . ? O2 C14 1.426(6) . ? O3 C17 1.350(6) . ? O3 C22 1.435(6) . ? O4 C23 1.425(6) . ? O4 C24 1.439(6) . ? O4 Li1 2.117(9) . ? O5 C26 1.411(6) . ? O5 C25 1.419(6) . ? O5 Li1 2.026(9) . ? C1 C6 1.409(6) . ? C1 C2 1.424(6) . ? C2 C3 1.375(6) . ? C2 C7 1.515(6) . ? C3 C4 1.386(6) . ? C4 C5 1.382(6) . ? C5 C6 1.398(6) . ? C6 C15 1.518(6) . ? C7 C8 1.495(7) . ? C8 C13 1.393(8) . ? C8 C9 1.391(7) . ? C9 C10 1.367(7) . ? C10 C11 1.423(8) . ? C11 C12 1.369(8) . ? C12 C13 1.362(8) . ? C15 C16 1.512(6) . ? C16 C21 1.385(7) . ? C16 C17 1.422(6) . ? C17 C18 1.373(7) . ? C18 C19 1.382(7) . ? C19 C20 1.352(7) . ? C20 C21 1.420(7) . ? C24 C25 1.491(7) . ? C24 Li1 2.709(10) . ? Li1 O1 1.897(8) 2 ? Li1 Li1 2.525(17) 2 ? 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 Li1 140.6(4) . . ? C1 O1 Li1 132.0(4) . 2 ? Li1 O1 Li1 84.5(4) . 2 ? C9 O2 C14 118.2(4) . . ? C17 O3 C22 116.4(5) . . ? C23 O4 C24 112.6(4) . . ? C23 O4 Li1 135.2(4) . . ? C24 O4 Li1 97.4(4) . . ? C26 O5 C25 113.0(4) . . ? C26 O5 Li1 132.1(4) . . ? C25 O5 Li1 112.6(4) . . ? O1 C1 C6 120.6(4) . . ? O1 C1 C2 120.2(4) . . ? C6 C1 C2 119.2(4) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 C7 123.5(4) . . ? C1 C2 C7 117.0(4) . . ? C2 C3 C4 121.7(4) . . ? C5 C4 C3 119.0(4) . . ? C4 C5 C6 121.7(4) . . ? C5 C6 C1 118.9(4) . . ? C5 C6 C15 121.8(4) . . ? C1 C6 C15 119.3(4) . . ? C8 C7 C2 115.3(4) . . ? C13 C8 C9 116.3(5) . . ? C13 C8 C7 121.0(5) . . ? C9 C8 C7 122.8(5) . . ? C10 C9 C8 123.0(5) . . ? C10 C9 O2 122.9(5) . . ? C8 C9 O2 114.2(4) . . ? C9 C10 C11 119.0(5) . . ? C12 C11 C10 118.3(5) . . ? C13 C12 C11 121.3(6) . . ? C12 C13 C8 122.2(6) . . ? C16 C15 C6 116.1(4) . . ? C21 C16 C17 117.1(5) . . ? C21 C16 C15 121.4(4) . . ? C17 C16 C15 121.5(4) . . ? O3 C17 C18 124.5(5) . . ? O3 C17 C16 114.5(4) . . ? C18 C17 C16 121.0(5) . . ? C17 C18 C19 119.7(5) . . ? C20 C19 C18 122.2(5) . . ? C19 C20 C21 118.2(6) . . ? C16 C21 C20 121.8(5) . . ? O4 C24 C25 111.4(4) . . ? O4 C24 Li1 50.8(3) . . ? C25 C24 Li1 81.2(3) . . ? O5 C25 C24 106.8(4) . . ? O1 Li1 O1 95.5(4) . 2 ? O1 Li1 O5 117.0(4) . . ? O1 Li1 O5 114.8(4) 2 . ? O1 Li1 O4 138.2(4) . . ? O1 Li1 O4 110.6(4) 2 . ? O5 Li1 O4 81.8(3) . . ? O1 Li1 Li1 48.4(3) . 2 ? O1 Li1 Li1 47.1(3) 2 2 ? O5 Li1 Li1 130.4(5) . 2 ? O4 Li1 Li1 144.3(5) . 2 ? O1 Li1 C24 163.2(4) . . ? O1 Li1 C24 101.2(3) 2 . ? O5 Li1 C24 57.0(3) . . ? O4 Li1 C24 31.78(18) . . ? Li1 Li1 C24 148.3(5) 2 . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.434 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.078 _chemical_compound_source DME #===END data_COMPOUND_5 _database_code_depnum_ccdc_archive 'CCDC 299155' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 594 _chemical_formula_moiety 'C48 H54 Na2 O4' _chemical_formula_sum 'C48 H54 Na2 O4' _chemical_formula_weight 740.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9157(5) _cell_length_b 25.073(2) _cell_length_c 10.1182(9) _cell_angle_alpha 90.00 _cell_angle_beta 111.526(4) _cell_angle_gamma 90.00 _cell_volume 2104.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26204 _diffrn_reflns_av_R_equivalents 0.2829 _diffrn_reflns_av_sigmaI/netI 0.3145 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.76 _reflns_number_total 4777 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0869P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4777 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3120 _refine_ls_R_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.2245 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _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 Na1 Na -0.00397(19) -0.04381(6) 1.10944(19) 0.0324(5) Uani 1 1 d . . . O1 O -0.0013(3) 0.04493(11) 1.1060(3) 0.0307(8) Uani 1 1 d . . . O2 O -0.1859(4) -0.10161(11) 1.1465(3) 0.0379(9) Uani 1 1 d . . . C1 C 0.0394(5) 0.08347(16) 1.2033(5) 0.0260(11) Uani 1 1 d . . . C2 C 0.1948(5) 0.08511(16) 1.3124(5) 0.0239(11) Uani 1 1 d . . . C3 C 0.2338(5) 0.12519(17) 1.4127(5) 0.0324(12) Uani 1 1 d . . . H3 H 0.3379 0.1255 1.4856 0.039 Uiso 1 1 calc R . . C4 C 0.1246(6) 0.16498(17) 1.4096(5) 0.0322(12) Uani 1 1 d . . . H4 H 0.1535 0.1925 1.4789 0.039 Uiso 1 1 calc R . . C5 C -0.0271(6) 0.16392(16) 1.3039(5) 0.0300(12) Uani 1 1 d . . . H5 H -0.1021 0.1912 1.3016 0.036 Uiso 1 1 calc R . . C6 C -0.0733(5) 0.12407(16) 1.2007(4) 0.0260(11) Uani 1 1 d . . . C7 C 0.3146(5) 0.04225(16) 1.3135(5) 0.0311(12) Uani 1 1 d . . . H7A H 0.4226 0.0529 1.3807 0.037 Uiso 1 1 calc R . . H7B H 0.3201 0.0402 1.2176 0.037 Uiso 1 1 calc R . . C8 C 0.2759(5) -0.01291(16) 1.3547(5) 0.0273(11) Uani 1 1 d . . . C9 C 0.3278(5) -0.05847(18) 1.3024(5) 0.0343(12) Uani 1 1 d . . . H9 H 0.3823 -0.0545 1.2380 0.041 Uiso 1 1 calc R . . C10 C 0.3006(5) -0.10891(18) 1.3435(5) 0.0357(13) Uani 1 1 d . . . H10 H 0.3385 -0.1393 1.3089 0.043 Uiso 1 1 calc R . . C11 C 0.2190(5) -0.11545(18) 1.4339(5) 0.0355(12) Uani 1 1 d . . . H11 H 0.2006 -0.1503 1.4617 0.043 Uiso 1 1 calc R . . C12 C 0.1634(5) -0.07141(17) 1.4847(5) 0.0373(13) Uani 1 1 d . . . H12 H 0.1055 -0.0759 1.5462 0.045 Uiso 1 1 calc R . . C13 C 0.1929(5) -0.02060(17) 1.4451(5) 0.0312(12) Uani 1 1 d . . . H13 H 0.1553 0.0095 1.4809 0.037 Uiso 1 1 calc R . . C14 C -0.2371(5) 0.12253(17) 1.0828(5) 0.0365(13) Uani 1 1 d . . . H14A H -0.2236 0.1284 0.9911 0.044 Uiso 1 1 calc R . . H14B H -0.2839 0.0866 1.0800 0.044 Uiso 1 1 calc R . . C15 C -0.3531(5) 0.16316(16) 1.0981(5) 0.0267(11) Uani 1 1 d . . . C16 C -0.3670(5) 0.21308(17) 1.0384(5) 0.0334(12) Uani 1 1 d . . . H16 H -0.3073 0.2213 0.9802 0.040 Uiso 1 1 calc R . . C17 C -0.4648(6) 0.25121(18) 1.0609(6) 0.0432(14) Uani 1 1 d . . . H17 H -0.4727 0.2853 1.0177 0.052 Uiso 1 1 calc R . . C18 C -0.5521(6) 0.2406(2) 1.1457(6) 0.0490(15) Uani 1 1 d . . . H18 H -0.6171 0.2674 1.1643 0.059 Uiso 1 1 calc R . . C19 C -0.5430(6) 0.1903(2) 1.2030(5) 0.0508(15) Uani 1 1 d . . . H19 H -0.6049 0.1821 1.2594 0.061 Uiso 1 1 calc R . . C20 C -0.4461(6) 0.15183(19) 1.1800(5) 0.0397(13) Uani 1 1 d . . . H20 H -0.4419 0.1173 1.2198 0.048 Uiso 1 1 calc R . . C21 C -0.1746(6) -0.15831(18) 1.1568(6) 0.0446(14) Uani 1 1 d . . . H21A H -0.2827 -0.1744 1.1103 0.054 Uiso 1 1 calc R . . H21B H -0.1321 -0.1692 1.2579 0.054 Uiso 1 1 calc R . . C22 C -0.0629(6) -0.17735(18) 1.0848(6) 0.0511(15) Uani 1 1 d . . . H22A H -0.1051 -0.1661 0.9851 0.077 Uiso 1 1 calc R . . H22B H -0.0556 -0.2164 1.0897 0.077 Uiso 1 1 calc R . . H22C H 0.0445 -0.1620 1.1328 0.077 Uiso 1 1 calc R . . C23 C -0.2975(6) -0.0807(2) 1.2049(6) 0.0482(15) Uani 1 1 d . . . H23A H -0.2590 -0.0881 1.3082 0.058 Uiso 1 1 calc R . . H23B H -0.4043 -0.0977 1.1590 0.058 Uiso 1 1 calc R . . C24 C -0.3110(6) -0.0216(2) 1.1793(6) 0.0575(17) Uani 1 1 d . . . H24A H -0.2055 -0.0050 1.2272 0.086 Uiso 1 1 calc R . . H24B H -0.3889 -0.0067 1.2169 0.086 Uiso 1 1 calc R . . H24C H -0.3476 -0.0147 1.0770 0.086 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 Na1 0.0305(11) 0.0272(10) 0.0385(12) -0.0011(9) 0.0116(9) -0.0010(8) O1 0.0294(18) 0.0268(17) 0.033(2) -0.0054(15) 0.0072(15) -0.0018(14) O2 0.040(2) 0.0279(19) 0.048(2) 0.0029(16) 0.0183(18) -0.0041(15) C1 0.028(3) 0.023(2) 0.027(3) 0.003(2) 0.010(3) -0.004(2) C2 0.018(3) 0.025(2) 0.027(3) 0.001(2) 0.006(2) -0.003(2) C3 0.027(3) 0.033(3) 0.029(3) 0.003(2) 0.001(2) -0.004(2) C4 0.031(3) 0.028(3) 0.028(3) 0.001(2) 0.000(3) 0.007(2) C5 0.036(3) 0.024(2) 0.029(3) -0.003(2) 0.011(3) 0.004(2) C6 0.024(3) 0.027(3) 0.024(3) 0.001(2) 0.006(2) 0.004(2) C7 0.021(3) 0.031(3) 0.042(3) 0.004(2) 0.012(2) 0.001(2) C8 0.020(3) 0.025(3) 0.030(3) 0.003(2) 0.001(2) 0.005(2) C9 0.023(3) 0.038(3) 0.039(3) 0.004(2) 0.007(2) 0.003(2) C10 0.031(3) 0.027(3) 0.042(3) -0.002(2) 0.005(3) 0.007(2) C11 0.038(3) 0.030(3) 0.035(3) 0.005(2) 0.008(3) -0.003(2) C12 0.041(3) 0.028(3) 0.043(3) 0.005(2) 0.015(3) 0.002(2) C13 0.030(3) 0.028(3) 0.038(3) 0.002(2) 0.016(3) 0.005(2) C14 0.028(3) 0.034(3) 0.035(3) -0.005(2) -0.002(3) 0.009(2) C15 0.022(3) 0.021(2) 0.033(3) -0.001(2) 0.006(2) 0.004(2) C16 0.032(3) 0.026(3) 0.039(3) 0.005(2) 0.009(3) 0.004(2) C17 0.047(4) 0.030(3) 0.043(4) 0.003(2) 0.005(3) 0.004(3) C18 0.041(4) 0.055(4) 0.039(4) -0.012(3) 0.001(3) 0.024(3) C19 0.031(3) 0.080(4) 0.039(4) 0.003(3) 0.009(3) 0.003(3) C20 0.031(3) 0.041(3) 0.037(4) 0.004(2) 0.001(3) 0.001(2) C21 0.049(3) 0.033(3) 0.050(4) 0.008(3) 0.016(3) -0.007(3) C22 0.042(3) 0.035(3) 0.074(4) -0.005(3) 0.019(3) -0.009(3) C23 0.039(3) 0.056(4) 0.060(4) -0.010(3) 0.031(3) -0.008(3) C24 0.050(4) 0.053(4) 0.083(5) -0.005(3) 0.041(4) 0.000(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 Na1 O1 2.198(3) 3_557 ? Na1 O1 2.226(3) . ? Na1 O2 2.306(3) . ? Na1 C9 2.908(4) . ? Na1 C8 2.906(5) . ? Na1 Na1 3.139(3) 3_557 ? O1 C1 1.331(5) . ? O1 Na1 2.198(3) 3_557 ? O2 C21 1.426(5) . ? O2 C23 1.430(5) . ? C1 C6 1.424(5) . ? C1 C2 1.420(6) . ? C2 C3 1.379(6) . ? C2 C7 1.512(5) . ? C3 C4 1.386(6) . ? C4 C5 1.383(6) . ? C5 C6 1.394(5) . ? C6 C14 1.509(6) . ? C7 C8 1.520(5) . ? C8 C13 1.385(6) . ? C8 C9 1.407(6) . ? C9 C10 1.380(6) . ? C10 C11 1.371(6) . ? C11 C12 1.384(6) . ? C12 C13 1.389(6) . ? C14 C15 1.499(5) . ? C15 C16 1.375(5) . ? C15 C20 1.399(6) . ? C16 C17 1.368(6) . ? C17 C18 1.380(7) . ? C18 C19 1.378(7) . ? C19 C20 1.371(6) . ? C21 C22 1.511(6) . ? C23 C24 1.500(6) . ? 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 O1 Na1 O1 89.60(12) 3_557 . ? O1 Na1 O2 115.19(13) 3_557 . ? O1 Na1 O2 130.01(13) . . ? O1 Na1 C9 106.11(13) 3_557 . ? O1 Na1 C9 97.04(13) . . ? O2 Na1 C9 114.48(13) . . ? O1 Na1 C8 121.77(13) 3_557 . ? O1 Na1 C8 74.68(12) . . ? O2 Na1 C8 117.61(13) . . ? C9 Na1 C8 28.01(11) . . ? O1 Na1 Na1 45.16(8) 3_557 3_557 ? O1 Na1 Na1 44.45(9) . 3_557 ? O2 Na1 Na1 138.93(12) . 3_557 ? C9 Na1 Na1 106.34(12) . 3_557 ? C8 Na1 Na1 100.45(11) . 3_557 ? C1 O1 Na1 130.0(3) . 3_557 ? C1 O1 Na1 135.7(3) . . ? Na1 O1 Na1 90.40(12) 3_557 . ? C21 O2 C23 112.1(3) . . ? C21 O2 Na1 127.1(3) . . ? C23 O2 Na1 118.3(3) . . ? O1 C1 C6 120.4(4) . . ? O1 C1 C2 121.3(4) . . ? C6 C1 C2 118.3(4) . . ? C3 C2 C1 120.2(4) . . ? C3 C2 C7 121.7(4) . . ? C1 C2 C7 118.0(4) . . ? C2 C3 C4 121.5(4) . . ? C3 C4 C5 118.9(4) . . ? C4 C5 C6 121.9(4) . . ? C5 C6 C1 119.1(4) . . ? C5 C6 C14 123.0(4) . . ? C1 C6 C14 117.9(4) . . ? C2 C7 C8 114.7(3) . . ? C13 C8 C9 117.7(4) . . ? C13 C8 C7 122.5(4) . . ? C9 C8 C7 119.7(4) . . ? C13 C8 Na1 91.6(3) . . ? C9 C8 Na1 76.1(2) . . ? C7 C8 Na1 102.6(3) . . ? C10 C9 C8 120.8(4) . . ? C10 C9 Na1 94.0(3) . . ? C8 C9 Na1 75.9(2) . . ? C11 C10 C9 120.4(4) . . ? C10 C11 C12 120.1(4) . . ? C11 C12 C13 119.6(5) . . ? C8 C13 C12 121.4(4) . . ? C15 C14 C6 113.9(4) . . ? C16 C15 C20 117.8(4) . . ? C16 C15 C14 121.8(4) . . ? C20 C15 C14 120.3(4) . . ? C17 C16 C15 121.6(5) . . ? C16 C17 C18 120.5(5) . . ? C17 C18 C19 118.6(5) . . ? C20 C19 C18 121.0(5) . . ? C19 C20 C15 120.4(5) . . ? O2 C21 C22 108.7(4) . . ? O2 C23 C24 108.3(4) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.76 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.364 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.067 _chemical_compound_source Et2O #===END data_COMPOUND_6 _database_code_depnum_ccdc_archive 'CCDC 299156' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 566 _chemical_formula_moiety 'C48 H54 Na2 O6' _chemical_formula_sum 'C48 H54 Na2 O6' _chemical_formula_weight 772.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2892(4) _cell_length_b 10.1342(5) _cell_length_c 23.5197(13) _cell_angle_alpha 81.467(2) _cell_angle_beta 87.774(2) _cell_angle_gamma 72.651(2) _cell_volume 2089.96(18) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9904 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22270 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 28.18 _reflns_number_total 9528 _reflns_number_gt 6243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.1471P)^2^+0.6017P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9528 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.2245 _refine_ls_wR_factor_gt 0.1905 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 Na1 Na 0.93203(11) 0.89974(9) 0.04574(4) 0.0277(2) Uani 1 1 d . . . Na2 Na 0.96864(12) 0.40613(10) 0.45408(4) 0.0320(3) Uani 1 1 d . . . O1 O 1.0105(2) 0.90023(17) -0.04699(7) 0.0288(4) Uani 1 1 d . . . O2 O 0.6976(2) 0.86982(19) 0.02659(8) 0.0345(4) Uani 1 1 d . . . O3 O 0.7725(2) 0.89885(19) 0.13375(8) 0.0354(4) Uani 1 1 d . . . O4 O 0.9818(2) 0.38835(17) 0.55133(7) 0.0327(4) Uani 1 1 d . . . O5 O 0.7770(2) 0.29238(19) 0.44688(8) 0.0370(5) Uani 1 1 d . . . O6 O 0.8741(2) 0.44400(19) 0.35522(8) 0.0372(5) Uani 1 1 d . . . C1 C 1.0714(3) 0.8124(2) -0.08306(10) 0.0266(5) Uani 1 1 d . . . C2 C 1.2144(3) 0.7113(3) -0.07077(11) 0.0283(5) Uani 1 1 d . . . C3 C 1.2821(3) 0.6228(3) -0.11032(12) 0.0329(6) Uani 1 1 d . . . H3 H 1.3780 0.5566 -0.1016 0.039 Uiso 1 1 calc R . . C4 C 1.2127(3) 0.6289(3) -0.16229(11) 0.0331(6) Uani 1 1 d . . . H4 H 1.2611 0.5691 -0.1893 0.040 Uiso 1 1 calc R . . C5 C 1.0714(3) 0.7239(2) -0.17400(11) 0.0300(6) Uani 1 1 d . . . H5 H 1.0226 0.7276 -0.2092 0.036 Uiso 1 1 calc R . . C6 C 0.9990(3) 0.8144(2) -0.13542(10) 0.0271(5) Uani 1 1 d . . . C7 C 1.2920(3) 0.7060(3) -0.01473(11) 0.0321(6) Uani 1 1 d . . . H7A H 1.3087 0.7978 -0.0140 0.039 Uiso 1 1 calc R . . H7B H 1.3923 0.6354 -0.0140 0.039 Uiso 1 1 calc R . . C8 C 1.2079(3) 0.6714(2) 0.03947(11) 0.0288(5) Uani 1 1 d . . . C9 C 1.2295(3) 0.7183(3) 0.08995(12) 0.0333(6) Uani 1 1 d . . . H9 H 1.2985 0.7708 0.0908 0.040 Uiso 1 1 calc R . . C10 C 1.1503(3) 0.6889(3) 0.13960(12) 0.0365(6) Uani 1 1 d . . . H10 H 1.1661 0.7214 0.1740 0.044 Uiso 1 1 calc R . . C11 C 1.0490(3) 0.6129(3) 0.13906(12) 0.0358(6) Uani 1 1 d . . . H11 H 0.9955 0.5932 0.1729 0.043 Uiso 1 1 calc R . . C12 C 1.0262(3) 0.5656(3) 0.08865(12) 0.0339(6) Uani 1 1 d . . . H12 H 0.9567 0.5135 0.0879 0.041 Uiso 1 1 calc R . . C13 C 1.1052(3) 0.5947(2) 0.03937(11) 0.0307(6) Uani 1 1 d . . . H13 H 1.0893 0.5618 0.0050 0.037 Uiso 1 1 calc R . . C14 C 0.8463(3) 0.9206(3) -0.15032(11) 0.0317(6) Uani 1 1 d . . . H14A H 0.7975 0.9501 -0.1142 0.038 Uiso 1 1 calc R . . H14B H 0.8628 1.0040 -0.1741 0.038 Uiso 1 1 calc R . . C15 C 0.7387(3) 0.8704(2) -0.18223(10) 0.0263(5) Uani 1 1 d . . . C16 C 0.6624(3) 0.9503(3) -0.23088(11) 0.0298(6) Uani 1 1 d . . . H16 H 0.6801 1.0368 -0.2453 0.036 Uiso 1 1 calc R . . C17 C 0.5594(3) 0.9055(3) -0.25925(12) 0.0369(6) Uani 1 1 d . . . H17 H 0.5088 0.9606 -0.2930 0.044 Uiso 1 1 calc R . . C18 C 0.5318(3) 0.7811(3) -0.23802(13) 0.0395(7) Uani 1 1 d . . . H18 H 0.4605 0.7513 -0.2567 0.047 Uiso 1 1 calc R . . C19 C 0.6073(3) 0.7003(3) -0.18987(12) 0.0367(6) Uani 1 1 d . . . H19 H 0.5894 0.6138 -0.1757 0.044 Uiso 1 1 calc R . . C20 C 0.7092(3) 0.7442(3) -0.16209(12) 0.0327(6) Uani 1 1 d . . . H20 H 0.7602 0.6877 -0.1287 0.039 Uiso 1 1 calc R . . C21 C 0.6989(4) 0.7689(3) -0.01027(13) 0.0427(7) Uani 1 1 d . . . H21A H 0.7164 0.6767 0.0128 0.064 Uiso 1 1 calc R . . H21B H 0.7796 0.7660 -0.0386 0.064 Uiso 1 1 calc R . . H21C H 0.6016 0.7951 -0.0302 0.064 Uiso 1 1 calc R . . C22 C 0.5925(3) 0.8709(3) 0.07212(12) 0.0375(6) Uani 1 1 d . . . H22A H 0.6047 0.7744 0.0913 0.045 Uiso 1 1 calc R . . H22B H 0.4883 0.9106 0.0568 0.045 Uiso 1 1 calc R . . C23 C 0.6208(3) 0.9580(3) 0.11423(12) 0.0384(7) Uani 1 1 d . . . H23A H 0.6047 1.0555 0.0955 0.046 Uiso 1 1 calc R . . H23B H 0.5508 0.9585 0.1471 0.046 Uiso 1 1 calc R . . C24 C 0.8010(4) 0.9515(3) 0.18392(12) 0.0435(7) Uani 1 1 d . . . H24A H 0.7740 1.0536 0.1762 0.065 Uiso 1 1 calc R . . H24B H 0.9082 0.9132 0.1941 0.065 Uiso 1 1 calc R . . H24C H 0.7403 0.9236 0.2159 0.065 Uiso 1 1 calc R . . C25 C 1.0099(3) 0.2812(2) 0.59217(10) 0.0277(5) Uani 1 1 d . . . C26 C 1.1513(3) 0.1755(3) 0.59662(11) 0.0304(6) Uani 1 1 d . . . C27 C 1.1778(3) 0.0616(3) 0.63978(11) 0.0320(6) Uani 1 1 d . . . H27 H 1.2723 -0.0089 0.6414 0.038 Uiso 1 1 calc R . . C28 C 1.0683(3) 0.0483(3) 0.68104(11) 0.0326(6) Uani 1 1 d . . . H28 H 1.0877 -0.0299 0.7105 0.039 Uiso 1 1 calc R . . C29 C 0.9308(3) 0.1521(2) 0.67789(11) 0.0302(6) Uani 1 1 d . . . H29 H 0.8561 0.1447 0.7059 0.036 Uiso 1 1 calc R . . C30 C 0.8995(3) 0.2664(2) 0.63489(10) 0.0285(5) Uani 1 1 d . . . C31 C 1.2728(3) 0.1916(3) 0.55335(12) 0.0346(6) Uani 1 1 d . . . H31A H 1.3697 0.1229 0.5670 0.042 Uiso 1 1 calc R . . H31B H 1.2843 0.2859 0.5524 0.042 Uiso 1 1 calc R . . C32 C 1.2438(3) 0.1721(3) 0.49241(11) 0.0309(6) Uani 1 1 d . . . C33 C 1.3022(3) 0.2400(3) 0.44573(12) 0.0355(6) Uani 1 1 d . . . H33 H 1.3561 0.3029 0.4520 0.043 Uiso 1 1 calc R . . C34 C 1.2833(4) 0.2176(3) 0.39044(12) 0.0394(7) Uani 1 1 d . . . H34 H 1.3252 0.2644 0.3591 0.047 Uiso 1 1 calc R . . C35 C 1.2036(3) 0.1275(3) 0.38011(12) 0.0371(6) Uani 1 1 d . . . H35 H 1.1919 0.1114 0.3420 0.045 Uiso 1 1 calc R . . C36 C 1.1415(3) 0.0613(3) 0.42595(12) 0.0379(6) Uani 1 1 d . . . H36 H 1.0844 0.0012 0.4193 0.046 Uiso 1 1 calc R . . C37 C 1.1624(3) 0.0825(3) 0.48181(12) 0.0353(6) Uani 1 1 d . . . H37 H 1.1208 0.0355 0.5131 0.042 Uiso 1 1 calc R . . C38 C 0.7524(3) 0.3845(3) 0.63199(12) 0.0333(6) Uani 1 1 d . . . H38A H 0.7748 0.4704 0.6389 0.040 Uiso 1 1 calc R . . H38B H 0.7107 0.4018 0.5926 0.040 Uiso 1 1 calc R . . C39 C 0.6329(3) 0.3593(2) 0.67402(11) 0.0300(6) Uani 1 1 d . . . C40 C 0.6264(3) 0.3971(3) 0.72886(12) 0.0327(6) Uani 1 1 d . . . H40 H 0.6967 0.4408 0.7395 0.039 Uiso 1 1 calc R . . C41 C 0.5190(3) 0.3721(3) 0.76832(12) 0.0354(6) Uani 1 1 d . . . H41 H 0.5173 0.3971 0.8058 0.042 Uiso 1 1 calc R . . C42 C 0.4143(3) 0.3106(3) 0.75293(12) 0.0353(6) Uani 1 1 d . . . H42 H 0.3407 0.2934 0.7798 0.042 Uiso 1 1 calc R . . C43 C 0.4169(3) 0.2742(3) 0.69840(13) 0.0365(6) Uani 1 1 d . . . H43 H 0.3439 0.2338 0.6875 0.044 Uiso 1 1 calc R . . C44 C 0.5266(3) 0.2969(3) 0.65973(12) 0.0351(6) Uani 1 1 d . . . H44 H 0.5295 0.2695 0.6227 0.042 Uiso 1 1 calc R . . C45 C 0.6836(4) 0.2749(3) 0.49500(14) 0.0476(8) Uani 1 1 d . . . H45A H 0.6086 0.3645 0.4989 0.071 Uiso 1 1 calc R . . H45B H 0.7457 0.2416 0.5299 0.071 Uiso 1 1 calc R . . H45C H 0.6319 0.2064 0.4893 0.071 Uiso 1 1 calc R . . C46 C 0.6916(4) 0.3348(3) 0.39480(13) 0.0408(7) Uani 1 1 d . . . H46A H 0.6147 0.4261 0.3962 0.049 Uiso 1 1 calc R . . H46B H 0.6392 0.2654 0.3897 0.049 Uiso 1 1 calc R . . C47 C 0.7966(4) 0.3465(3) 0.34566(13) 0.0424(7) Uani 1 1 d . . . H47A H 0.8701 0.2541 0.3429 0.051 Uiso 1 1 calc R . . H47B H 0.7389 0.3791 0.3091 0.051 Uiso 1 1 calc R . . C48 C 0.9560(4) 0.4793(3) 0.30593(12) 0.0411(7) Uani 1 1 d . . . H48A H 1.0374 0.3966 0.2985 0.062 Uiso 1 1 calc R . . H48B H 0.9991 0.5529 0.3127 0.062 Uiso 1 1 calc R . . H48C H 0.8880 0.5128 0.2726 0.062 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 Na1 0.0293(6) 0.0297(5) 0.0274(5) -0.0126(4) 0.0101(4) -0.0110(4) Na2 0.0402(6) 0.0319(5) 0.0274(5) -0.0074(4) 0.0045(4) -0.0147(4) O1 0.0338(10) 0.0272(8) 0.0290(9) -0.0153(7) 0.0112(8) -0.0106(7) O2 0.0313(11) 0.0448(10) 0.0330(10) -0.0148(8) 0.0095(8) -0.0166(8) O3 0.0316(11) 0.0440(10) 0.0317(10) -0.0180(8) 0.0098(8) -0.0081(8) O4 0.0444(12) 0.0302(9) 0.0260(9) -0.0055(7) 0.0066(8) -0.0150(8) O5 0.0406(12) 0.0374(10) 0.0343(10) -0.0065(8) 0.0004(9) -0.0129(9) O6 0.0463(12) 0.0365(10) 0.0325(10) -0.0088(8) 0.0015(9) -0.0162(9) C1 0.0316(14) 0.0264(11) 0.0279(12) -0.0113(10) 0.0118(10) -0.0155(10) C2 0.0268(14) 0.0299(12) 0.0305(13) -0.0084(10) 0.0075(10) -0.0109(10) C3 0.0264(14) 0.0313(13) 0.0396(15) -0.0093(11) 0.0128(11) -0.0062(11) C4 0.0369(16) 0.0337(13) 0.0322(14) -0.0187(11) 0.0147(12) -0.0108(11) C5 0.0364(15) 0.0312(12) 0.0266(13) -0.0119(10) 0.0093(11) -0.0135(11) C6 0.0300(14) 0.0265(11) 0.0277(12) -0.0103(10) 0.0101(10) -0.0111(10) C7 0.0263(14) 0.0380(13) 0.0350(14) -0.0100(11) 0.0070(11) -0.0125(11) C8 0.0283(14) 0.0280(12) 0.0288(13) -0.0049(10) 0.0015(11) -0.0060(10) C9 0.0330(15) 0.0318(13) 0.0372(15) -0.0073(11) -0.0007(12) -0.0114(11) C10 0.0460(18) 0.0337(13) 0.0289(14) -0.0079(11) 0.0009(12) -0.0088(12) C11 0.0431(17) 0.0302(13) 0.0306(14) -0.0023(11) 0.0070(12) -0.0072(12) C12 0.0373(16) 0.0283(12) 0.0374(15) -0.0037(11) 0.0047(12) -0.0126(11) C13 0.0368(15) 0.0252(12) 0.0314(13) -0.0067(10) 0.0047(11) -0.0108(11) C14 0.0380(16) 0.0255(12) 0.0325(14) -0.0110(10) 0.0025(12) -0.0075(11) C15 0.0256(13) 0.0268(11) 0.0262(12) -0.0138(10) 0.0111(10) -0.0040(10) C16 0.0298(14) 0.0302(12) 0.0284(13) -0.0095(10) 0.0124(11) -0.0063(10) C17 0.0324(16) 0.0433(15) 0.0324(15) -0.0118(12) 0.0026(12) -0.0043(12) C18 0.0300(16) 0.0445(15) 0.0482(17) -0.0234(14) 0.0071(13) -0.0103(12) C19 0.0395(17) 0.0310(13) 0.0443(16) -0.0144(12) 0.0123(13) -0.0147(12) C20 0.0368(16) 0.0284(12) 0.0314(14) -0.0085(10) 0.0063(11) -0.0058(11) C21 0.0423(18) 0.0521(17) 0.0414(16) -0.0221(14) 0.0058(14) -0.0186(14) C22 0.0289(15) 0.0472(15) 0.0377(15) -0.0067(12) 0.0111(12) -0.0142(12) C23 0.0349(16) 0.0397(14) 0.0376(15) -0.0128(12) 0.0156(13) -0.0049(12) C24 0.0499(19) 0.0565(18) 0.0345(15) -0.0227(13) 0.0171(14) -0.0257(15) C25 0.0369(15) 0.0287(12) 0.0221(12) -0.0085(10) 0.0036(11) -0.0148(11) C26 0.0337(15) 0.0356(13) 0.0269(13) -0.0133(10) 0.0029(11) -0.0141(11) C27 0.0321(15) 0.0343(13) 0.0316(14) -0.0159(11) 0.0023(11) -0.0079(11) C28 0.0440(17) 0.0270(12) 0.0279(13) -0.0080(10) 0.0039(12) -0.0108(11) C29 0.0393(16) 0.0302(12) 0.0248(12) -0.0103(10) 0.0082(11) -0.0140(11) C30 0.0358(15) 0.0277(12) 0.0253(12) -0.0093(10) 0.0056(11) -0.0124(11) C31 0.0335(15) 0.0426(14) 0.0329(14) -0.0123(12) 0.0049(12) -0.0164(12) C32 0.0286(14) 0.0337(13) 0.0312(14) -0.0117(11) 0.0066(11) -0.0076(11) C33 0.0374(16) 0.0356(13) 0.0393(15) -0.0146(12) 0.0104(12) -0.0164(12) C34 0.0480(18) 0.0389(14) 0.0316(15) -0.0072(12) 0.0116(13) -0.0138(13) C35 0.0411(17) 0.0405(15) 0.0293(14) -0.0134(12) 0.0073(12) -0.0081(12) C36 0.0429(17) 0.0423(15) 0.0361(15) -0.0173(12) 0.0069(13) -0.0190(13) C37 0.0400(17) 0.0401(14) 0.0310(14) -0.0124(11) 0.0101(12) -0.0172(12) C38 0.0388(16) 0.0277(12) 0.0323(14) -0.0054(10) 0.0076(12) -0.0086(11) C39 0.0347(15) 0.0220(11) 0.0302(13) -0.0051(10) 0.0032(11) -0.0035(10) C40 0.0325(15) 0.0330(13) 0.0358(14) -0.0146(11) 0.0057(11) -0.0105(11) C41 0.0340(16) 0.0355(13) 0.0350(14) -0.0136(11) 0.0066(12) -0.0046(11) C42 0.0310(15) 0.0307(13) 0.0409(16) -0.0078(11) 0.0074(12) -0.0038(11) C43 0.0325(16) 0.0303(13) 0.0482(17) -0.0087(12) -0.0018(13) -0.0099(11) C44 0.0412(17) 0.0299(13) 0.0347(15) -0.0106(11) 0.0008(12) -0.0086(11) C45 0.050(2) 0.0491(17) 0.0435(18) -0.0080(14) 0.0073(15) -0.0140(15) C46 0.0403(17) 0.0416(15) 0.0425(17) -0.0056(13) -0.0045(13) -0.0148(13) C47 0.053(2) 0.0425(15) 0.0366(16) -0.0098(13) -0.0065(14) -0.0192(14) C48 0.0433(18) 0.0462(16) 0.0337(15) -0.0066(13) 0.0019(13) -0.0131(13) _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 Na1 O1 2.2493(18) 2_775 ? Na1 O1 2.2723(19) . ? Na1 O2 2.355(2) . ? Na1 O3 2.499(2) . ? Na1 C8 2.912(3) . ? Na1 C9 2.953(3) . ? Na1 C13 3.053(3) . ? Na1 Na1 3.2212(18) 2_775 ? Na2 O4 2.2481(18) 2_766 ? Na2 O4 2.273(2) . ? Na2 O5 2.415(2) . ? Na2 O6 2.453(2) . ? Na2 C32 2.983(3) . ? Na2 C33 3.068(3) . ? Na2 Na2 3.2563(19) 2_766 ? O1 C1 1.311(3) . ? O1 Na1 2.2493(18) 2_775 ? O2 C22 1.419(3) . ? O2 C21 1.433(3) . ? O3 C23 1.421(4) . ? O3 C24 1.429(3) . ? O4 C25 1.308(3) . ? O4 Na2 2.2481(18) 2_766 ? O5 C45 1.422(4) . ? O5 C46 1.425(3) . ? O6 C48 1.422(3) . ? O6 C47 1.431(3) . ? C1 C6 1.421(4) . ? C1 C2 1.424(4) . ? C2 C3 1.390(4) . ? C2 C7 1.513(4) . ? C3 C4 1.389(4) . ? C4 C5 1.386(4) . ? C5 C6 1.396(3) . ? C6 C14 1.520(4) . ? C7 C8 1.520(3) . ? C8 C9 1.385(4) . ? C8 C13 1.399(4) . ? C9 C10 1.398(4) . ? C10 C11 1.383(4) . ? C11 C12 1.389(4) . ? C12 C13 1.390(4) . ? C14 C15 1.514(4) . ? C15 C16 1.383(4) . ? C15 C20 1.398(3) . ? C16 C17 1.402(4) . ? C17 C18 1.378(4) . ? C18 C19 1.375(4) . ? C19 C20 1.381(4) . ? C22 C23 1.499(4) . ? C25 C26 1.422(4) . ? C25 C30 1.432(3) . ? C26 C27 1.388(4) . ? C26 C31 1.519(4) . ? C27 C28 1.400(4) . ? C28 C29 1.388(4) . ? C29 C30 1.387(3) . ? C30 C38 1.520(4) . ? C31 C32 1.521(4) . ? C32 C33 1.388(4) . ? C32 C37 1.395(4) . ? C33 C34 1.379(4) . ? C34 C35 1.387(4) . ? C35 C36 1.383(4) . ? C36 C37 1.393(4) . ? C38 C39 1.511(4) . ? C39 C44 1.396(4) . ? C39 C40 1.393(4) . ? C40 C41 1.390(4) . ? C41 C42 1.386(4) . ? C42 C43 1.384(4) . ? C43 C44 1.388(4) . ? C46 C47 1.497(4) . ? 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 O1 Na1 O1 89.14(6) 2_775 . ? O1 Na1 O2 128.58(8) 2_775 . ? O1 Na1 O2 94.36(7) . . ? O1 Na1 O3 100.06(7) 2_775 . ? O1 Na1 O3 162.32(8) . . ? O2 Na1 O3 68.09(7) . . ? O1 Na1 C8 109.63(8) 2_775 . ? O1 Na1 C8 70.52(7) . . ? O2 Na1 C8 119.85(7) . . ? O3 Na1 C8 119.32(7) . . ? O1 Na1 C9 94.44(7) 2_775 . ? O1 Na1 C9 92.28(8) . . ? O2 Na1 C9 136.48(7) . . ? O3 Na1 C9 101.92(8) . . ? C8 Na1 C9 27.31(7) . . ? O1 Na1 C13 136.63(8) 2_775 . ? O1 Na1 C13 76.04(7) . . ? O2 Na1 C13 93.50(7) . . ? O3 Na1 C13 106.10(7) . . ? C8 Na1 C13 27.00(7) . . ? C9 Na1 C13 46.94(7) . . ? O1 Na1 Na1 44.86(5) 2_775 2_775 ? O1 Na1 Na1 44.28(4) . 2_775 ? O2 Na1 Na1 119.27(7) . 2_775 ? O3 Na1 Na1 142.57(6) . 2_775 ? C8 Na1 Na1 89.96(6) . 2_775 ? C9 Na1 Na1 94.71(7) . 2_775 ? C13 Na1 Na1 109.72(6) . 2_775 ? O4 Na2 O4 87.84(7) 2_766 . ? O4 Na2 O5 145.74(9) 2_766 . ? O4 Na2 O5 99.33(7) . . ? O4 Na2 O6 95.88(7) 2_766 . ? O4 Na2 O6 162.96(9) . . ? O5 Na2 O6 68.54(7) . . ? O4 Na2 C32 109.97(8) 2_766 . ? O4 Na2 C32 73.01(8) . . ? O5 Na2 C32 104.15(7) . . ? O6 Na2 C32 120.63(8) . . ? O4 Na2 C33 93.42(8) 2_766 . ? O4 Na2 C33 92.35(8) . . ? O5 Na2 C33 119.45(8) . . ? O6 Na2 C33 103.98(8) . . ? C32 Na2 C33 26.47(7) . . ? O4 Na2 Na2 44.22(5) 2_766 2_766 ? O4 Na2 Na2 43.62(5) . 2_766 ? O5 Na2 Na2 133.14(7) . 2_766 ? O6 Na2 Na2 137.56(7) . 2_766 ? C32 Na2 Na2 91.83(7) . 2_766 ? C33 Na2 Na2 94.00(7) . 2_766 ? C1 O1 Na1 122.94(14) . 2_775 ? C1 O1 Na1 139.96(15) . . ? Na1 O1 Na1 90.86(6) 2_775 . ? C22 O2 C21 112.7(2) . . ? C22 O2 Na1 118.56(16) . . ? C21 O2 Na1 116.73(17) . . ? C23 O3 C24 112.4(2) . . ? C23 O3 Na1 105.83(15) . . ? C24 O3 Na1 122.61(16) . . ? C25 O4 Na2 130.72(15) . 2_766 ? C25 O4 Na2 132.39(15) . . ? Na2 O4 Na2 92.16(7) 2_766 . ? C45 O5 C46 111.2(2) . . ? C45 O5 Na2 119.48(17) . . ? C46 O5 Na2 115.05(15) . . ? C48 O6 C47 111.9(2) . . ? C48 O6 Na2 123.78(17) . . ? C47 O6 Na2 112.68(16) . . ? O1 C1 C6 121.9(2) . . ? O1 C1 C2 120.4(2) . . ? C6 C1 C2 117.7(2) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 C7 121.2(2) . . ? C1 C2 C7 118.4(2) . . ? C4 C3 C2 121.5(3) . . ? C3 C4 C5 118.7(2) . . ? C4 C5 C6 121.7(2) . . ? C5 C6 C1 120.0(2) . . ? C5 C6 C14 120.5(2) . . ? C1 C6 C14 119.5(2) . . ? C2 C7 C8 115.5(2) . . ? C9 C8 C13 118.6(2) . . ? C9 C8 C7 120.2(2) . . ? C13 C8 C7 121.2(2) . . ? C9 C8 Na1 78.01(16) . . ? C13 C8 Na1 82.15(16) . . ? C7 C8 Na1 108.51(16) . . ? C8 C9 C10 120.4(2) . . ? C8 C9 Na1 74.68(16) . . ? C10 C9 Na1 84.70(17) . . ? C11 C10 C9 120.6(3) . . ? C10 C11 C12 119.5(2) . . ? C13 C12 C11 119.8(2) . . ? C12 C13 C8 121.1(2) . . ? C12 C13 Na1 85.16(15) . . ? C8 C13 Na1 70.85(14) . . ? C15 C14 C6 115.5(2) . . ? C16 C15 C20 117.9(2) . . ? C16 C15 C14 121.1(2) . . ? C20 C15 C14 120.9(2) . . ? C15 C16 C17 120.9(2) . . ? C18 C17 C16 119.7(3) . . ? C19 C18 C17 120.0(3) . . ? C18 C19 C20 120.2(2) . . ? C19 C20 C15 121.2(3) . . ? O2 C22 C23 108.4(2) . . ? O3 C23 C22 107.8(2) . . ? O4 C25 C26 121.7(2) . . ? O4 C25 C30 121.2(2) . . ? C26 C25 C30 117.1(2) . . ? C27 C26 C25 120.7(2) . . ? C27 C26 C31 121.0(2) . . ? C25 C26 C31 118.2(2) . . ? C26 C27 C28 121.4(3) . . ? C29 C28 C27 118.5(2) . . ? C28 C29 C30 121.7(2) . . ? C29 C30 C25 120.5(2) . . ? C29 C30 C38 122.7(2) . . ? C25 C30 C38 116.7(2) . . ? C26 C31 C32 115.2(2) . . ? C33 C32 C37 118.1(2) . . ? C33 C32 C31 120.5(2) . . ? C37 C32 C31 121.3(2) . . ? C33 C32 Na2 80.18(17) . . ? C37 C32 Na2 86.61(17) . . ? C31 C32 Na2 104.64(17) . . ? C34 C33 C32 121.1(2) . . ? C34 C33 Na2 92.00(19) . . ? C32 C33 Na2 73.36(16) . . ? C33 C34 C35 120.6(2) . . ? C36 C35 C34 119.2(3) . . ? C37 C36 C35 120.1(3) . . ? C36 C37 C32 120.8(2) . . ? C39 C38 C30 115.2(2) . . ? C44 C39 C40 117.8(2) . . ? C44 C39 C38 121.6(2) . . ? C40 C39 C38 120.6(2) . . ? C41 C40 C39 121.2(3) . . ? C42 C41 C40 119.9(3) . . ? C41 C42 C43 120.0(3) . . ? C42 C43 C44 119.6(3) . . ? C43 C44 C39 121.5(3) . . ? O5 C46 C47 108.7(2) . . ? O6 C47 C46 108.6(2) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.504 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.078 _chemical_compound_source DME #===END data_COMPOUND_7 _database_code_depnum_ccdc_archive 'CCDC 299157' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 396 _chemical_formula_moiety 'C52 H58 Na2 O8' _chemical_formula_sum 'C52 H58 Na2 O8' _chemical_formula_weight 856.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5356(19) _cell_length_b 10.974(2) _cell_length_c 21.326(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.24(3) _cell_angle_gamma 90.00 _cell_volume 2231.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cubic _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12461 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.1250 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.71 _reflns_number_total 5151 _reflns_number_gt 2862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0774P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5151 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1406 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 Na1 Na 0.11274(9) 0.40446(8) 0.47151(4) 0.0215(2) Uani 1 1 d . . . O1 O 0.11058(15) 0.60065(14) 0.49568(7) 0.0204(4) Uani 1 1 d . . . O2 O 0.34481(15) 0.45810(15) 0.41018(7) 0.0233(4) Uani 1 1 d . . . O3 O 0.11146(17) 0.60559(15) 0.69789(7) 0.0287(4) Uani 1 1 d . . . O4 O 0.21613(18) 0.28684(15) 0.55011(7) 0.0305(4) Uani 1 1 d . . . C1 C 0.1923(2) 0.6925(2) 0.48224(10) 0.0158(5) Uani 1 1 d . . . C2 C 0.2303(2) 0.7225(2) 0.41980(10) 0.0181(5) Uani 1 1 d . . . C3 C 0.3183(2) 0.8210(2) 0.40863(11) 0.0226(6) Uani 1 1 d . . . H3 H 0.3428 0.8399 0.3666 0.027 Uiso 1 1 calc R . . C4 C 0.3711(2) 0.8923(2) 0.45646(11) 0.0260(6) Uani 1 1 d . . . H4 H 0.4307 0.9595 0.4477 0.031 Uiso 1 1 calc R . . C5 C 0.3353(2) 0.8635(2) 0.51772(11) 0.0215(5) Uani 1 1 d . . . H5 H 0.3711 0.9119 0.5511 0.026 Uiso 1 1 calc R . . C6 C 0.2488(2) 0.7663(2) 0.53130(10) 0.0179(5) Uani 1 1 d . . . C7 C 0.1758(2) 0.6464(2) 0.36549(10) 0.0201(5) Uani 1 1 d . . . H7A H 0.1160 0.5803 0.3822 0.024 Uiso 1 1 calc R . . H7B H 0.1165 0.6984 0.3382 0.024 Uiso 1 1 calc R . . C8 C 0.2912(2) 0.5908(2) 0.32645(10) 0.0188(5) Uani 1 1 d . . . C9 C 0.3766(2) 0.4981(2) 0.35041(10) 0.0193(5) Uani 1 1 d . . . C10 C 0.4855(2) 0.4494(2) 0.31523(11) 0.0247(6) Uani 1 1 d . . . H10 H 0.5433 0.3869 0.3322 0.030 Uiso 1 1 calc R . . C11 C 0.5092(3) 0.4932(2) 0.25472(11) 0.0268(6) Uani 1 1 d . . . H11 H 0.5830 0.4599 0.2303 0.032 Uiso 1 1 calc R . . C12 C 0.4269(2) 0.5835(2) 0.23051(11) 0.0266(6) Uani 1 1 d . . . H12 H 0.4439 0.6134 0.1894 0.032 Uiso 1 1 calc R . . C13 C 0.3184(2) 0.6318(2) 0.26590(10) 0.0221(6) Uani 1 1 d . . . H13 H 0.2613 0.6941 0.2484 0.027 Uiso 1 1 calc R . . C14 C 0.4452(2) 0.3791(2) 0.43969(11) 0.0282(6) Uani 1 1 d . . . H14A H 0.4528 0.3034 0.4156 0.042 Uiso 1 1 calc R . . H14B H 0.4146 0.3605 0.4824 0.042 Uiso 1 1 calc R . . H14C H 0.5368 0.4196 0.4412 0.042 Uiso 1 1 calc R . . C15 C 0.2174(2) 0.7307(2) 0.59806(10) 0.0218(5) Uani 1 1 d . . . H15A H 0.2807 0.7773 0.6261 0.026 Uiso 1 1 calc R . . H15B H 0.2403 0.6433 0.6033 0.026 Uiso 1 1 calc R . . C16 C 0.0681(2) 0.7508(2) 0.61960(10) 0.0190(5) Uani 1 1 d . . . C17 C 0.0170(2) 0.6839(2) 0.67086(10) 0.0210(5) Uani 1 1 d . . . C18 C -0.1198(2) 0.6988(2) 0.69128(11) 0.0248(6) Uani 1 1 d . . . H18 H -0.1540 0.6519 0.7254 0.030 Uiso 1 1 calc R . . C19 C -0.2062(3) 0.7824(2) 0.66160(11) 0.0287(6) Uani 1 1 d . . . H19 H -0.2998 0.7927 0.6757 0.034 Uiso 1 1 calc R . . C20 C -0.1581(3) 0.8511(2) 0.61164(12) 0.0293(6) Uani 1 1 d . . . H20 H -0.2174 0.9089 0.5916 0.035 Uiso 1 1 calc R . . C21 C -0.0205(2) 0.8337(2) 0.59129(11) 0.0224(6) Uani 1 1 d . . . H21 H 0.0131 0.8803 0.5570 0.027 Uiso 1 1 calc R . . C22 C 0.0665(3) 0.5369(2) 0.75120(12) 0.0342(7) Uani 1 1 d . . . H22A H 0.0429 0.5927 0.7854 0.051 Uiso 1 1 calc R . . H22B H 0.1422 0.4824 0.7647 0.051 Uiso 1 1 calc R . . H22C H -0.0163 0.4886 0.7399 0.051 Uiso 1 1 calc R . . C23 C 0.1724(3) 0.1667(2) 0.56778(12) 0.0343(7) Uani 1 1 d . . . H23A H 0.1972 0.1071 0.5348 0.041 Uiso 1 1 calc R . . H23B H 0.0696 0.1643 0.5742 0.041 Uiso 1 1 calc R . . C24 C 0.2487(3) 0.1377(2) 0.62814(11) 0.0362(7) Uani 1 1 d . . . H24A H 0.1922 0.0837 0.6553 0.043 Uiso 1 1 calc R . . H24B H 0.3404 0.0987 0.6199 0.043 Uiso 1 1 calc R . . C25 C 0.2672(3) 0.2619(3) 0.65738(12) 0.0434(8) Uani 1 1 d . . . H25A H 0.1822 0.2869 0.6806 0.052 Uiso 1 1 calc R . . H25B H 0.3489 0.2635 0.6862 0.052 Uiso 1 1 calc R . . C26 C 0.2909(3) 0.3416(3) 0.60163(12) 0.0450(8) Uani 1 1 d . . . H26A H 0.2551 0.4248 0.6097 0.054 Uiso 1 1 calc R . . H26B H 0.3922 0.3469 0.5921 0.054 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 Na1 0.0194(5) 0.0207(5) 0.0244(5) 0.0000(4) 0.0032(4) -0.0012(4) O1 0.0201(8) 0.0183(8) 0.0230(9) 0.0001(7) 0.0065(7) -0.0058(7) O2 0.0224(9) 0.0283(10) 0.0192(9) 0.0051(7) 0.0037(7) 0.0060(8) O3 0.0289(9) 0.0316(10) 0.0256(9) 0.0085(8) 0.0040(8) 0.0044(8) O4 0.0386(10) 0.0265(10) 0.0263(9) 0.0060(8) -0.0058(8) -0.0043(8) C1 0.0114(11) 0.0143(12) 0.0216(12) 0.0005(10) 0.0029(9) 0.0032(10) C2 0.0153(11) 0.0156(12) 0.0233(12) 0.0002(10) 0.0012(10) 0.0041(10) C3 0.0231(13) 0.0204(13) 0.0244(13) 0.0052(11) 0.0080(11) 0.0010(11) C4 0.0233(13) 0.0183(13) 0.0364(15) 0.0014(12) 0.0069(12) -0.0061(11) C5 0.0173(12) 0.0172(12) 0.0301(14) -0.0066(11) -0.0007(11) 0.0004(10) C6 0.0140(11) 0.0202(12) 0.0195(12) -0.0022(11) 0.0010(10) 0.0029(10) C7 0.0190(12) 0.0226(13) 0.0187(12) 0.0000(11) 0.0007(10) 0.0034(11) C8 0.0158(11) 0.0207(12) 0.0200(12) -0.0025(11) -0.0001(10) -0.0011(10) C9 0.0188(12) 0.0227(13) 0.0164(12) 0.0002(11) 0.0018(10) -0.0026(11) C10 0.0223(13) 0.0282(14) 0.0236(13) -0.0024(11) 0.0005(11) 0.0073(11) C11 0.0229(13) 0.0365(15) 0.0210(13) -0.0075(12) 0.0037(11) 0.0046(12) C12 0.0263(13) 0.0355(15) 0.0179(12) -0.0004(12) 0.0009(11) -0.0047(12) C13 0.0213(12) 0.0248(13) 0.0203(13) 0.0021(11) -0.0011(10) -0.0002(11) C14 0.0234(13) 0.0353(15) 0.0258(13) 0.0092(12) 0.0009(11) 0.0094(12) C15 0.0159(12) 0.0262(13) 0.0232(13) -0.0033(11) 0.0012(10) 0.0007(11) C16 0.0194(12) 0.0213(13) 0.0164(12) -0.0072(10) 0.0009(10) 0.0014(11) C17 0.0231(13) 0.0202(13) 0.0197(12) -0.0033(11) 0.0006(11) -0.0007(11) C18 0.0261(14) 0.0273(14) 0.0210(12) -0.0055(12) 0.0056(11) -0.0040(12) C19 0.0224(13) 0.0333(15) 0.0305(14) -0.0131(13) 0.0044(11) 0.0037(12) C20 0.0265(14) 0.0314(15) 0.0301(14) -0.0048(13) -0.0034(12) 0.0088(12) C21 0.0238(13) 0.0227(13) 0.0208(12) -0.0023(11) -0.0007(10) 0.0017(11) C22 0.0400(16) 0.0342(16) 0.0284(14) 0.0101(13) 0.0025(12) -0.0024(13) C23 0.0435(16) 0.0250(15) 0.0342(15) 0.0033(13) -0.0043(13) 0.0002(13) C24 0.0516(18) 0.0315(16) 0.0257(14) 0.0073(13) 0.0036(13) 0.0050(14) C25 0.062(2) 0.0404(18) 0.0277(15) 0.0005(14) -0.0015(15) -0.0003(16) C26 0.069(2) 0.0350(17) 0.0315(16) 0.0005(14) -0.0055(15) -0.0117(16) _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 Na1 O1 2.2139(18) . ? Na1 O1 2.2450(18) 3_566 ? Na1 O4 2.3312(18) . ? Na1 O2 2.6415(19) . ? Na1 C21 3.064(3) 3_566 ? Na1 C16 3.102(2) 3_566 ? Na1 Na1 3.2432(18) 3_566 ? O1 C1 1.307(3) . ? O1 Na1 2.2450(18) 3_566 ? O2 C9 1.383(3) . ? O2 C14 1.435(3) . ? O3 C17 1.371(3) . ? O3 C22 1.431(3) . ? O4 C23 1.434(3) . ? O4 C26 1.439(3) . ? C1 C2 1.420(3) . ? C1 C6 1.427(3) . ? C2 C3 1.390(3) . ? C2 C7 1.517(3) . ? C3 C4 1.379(3) . ? C4 C5 1.388(3) . ? C5 C6 1.380(3) . ? C6 C15 1.507(3) . ? C7 C8 1.511(3) . ? C8 C13 1.392(3) . ? C8 C9 1.399(3) . ? C9 C10 1.390(3) . ? C10 C11 1.396(3) . ? C11 C12 1.364(3) . ? C12 C13 1.388(3) . ? C15 C16 1.514(3) . ? C16 C21 1.379(3) . ? C16 C17 1.405(3) . ? C16 Na1 3.102(2) 3_566 ? C17 C18 1.386(3) . ? C18 C19 1.385(3) . ? C19 C20 1.385(4) . ? C20 C21 1.397(3) . ? C21 Na1 3.064(2) 3_566 ? C23 C24 1.510(3) . ? C24 C25 1.509(4) . ? C25 C26 1.494(4) . ? 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 O1 Na1 O1 86.67(6) . 3_566 ? O1 Na1 O4 112.05(7) . . ? O1 Na1 O4 99.26(7) 3_566 . ? O1 Na1 O2 84.68(6) . . ? O1 Na1 O2 163.25(6) 3_566 . ? O4 Na1 O2 97.28(6) . . ? O1 Na1 C21 158.17(7) . 3_566 ? O1 Na1 C21 81.02(6) 3_566 3_566 ? O4 Na1 C21 87.81(7) . 3_566 ? O2 Na1 C21 102.32(6) . 3_566 ? O1 Na1 C16 132.39(7) . 3_566 ? O1 Na1 C16 69.88(6) 3_566 3_566 ? O4 Na1 C16 112.25(7) . 3_566 ? O2 Na1 C16 106.07(6) . 3_566 ? C21 Na1 C16 25.83(6) 3_566 3_566 ? O1 Na1 Na1 43.71(4) . 3_566 ? O1 Na1 Na1 42.96(4) 3_566 3_566 ? O4 Na1 Na1 111.57(6) . 3_566 ? O2 Na1 Na1 126.83(6) . 3_566 ? C21 Na1 Na1 121.71(6) 3_566 3_566 ? C16 Na1 Na1 102.84(6) 3_566 3_566 ? C1 O1 Na1 133.89(13) . . ? C1 O1 Na1 130.89(13) . 3_566 ? Na1 O1 Na1 93.33(6) . 3_566 ? C9 O2 C14 116.56(17) . . ? C9 O2 Na1 135.60(13) . . ? C14 O2 Na1 101.96(12) . . ? C17 O3 C22 117.78(19) . . ? C23 O4 C26 109.10(18) . . ? C23 O4 Na1 125.13(14) . . ? C26 O4 Na1 121.64(15) . . ? O1 C1 C2 122.6(2) . . ? O1 C1 C6 120.0(2) . . ? C2 C1 C6 117.3(2) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 C7 120.1(2) . . ? C1 C2 C7 120.0(2) . . ? C4 C3 C2 122.2(2) . . ? C3 C4 C5 118.5(2) . . ? C6 C5 C4 121.5(2) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 C15 121.3(2) . . ? C1 C6 C15 118.0(2) . . ? C8 C7 C2 113.25(18) . . ? C13 C8 C9 117.6(2) . . ? C13 C8 C7 121.3(2) . . ? C9 C8 C7 121.1(2) . . ? O2 C9 C10 122.9(2) . . ? O2 C9 C8 116.0(2) . . ? C10 C9 C8 121.2(2) . . ? C9 C10 C11 119.4(2) . . ? C12 C11 C10 120.3(2) . . ? C11 C12 C13 120.0(2) . . ? C12 C13 C8 121.6(2) . . ? C6 C15 C16 116.06(19) . . ? C21 C16 C17 118.1(2) . . ? C21 C16 C15 122.6(2) . . ? C17 C16 C15 119.3(2) . . ? C21 C16 Na1 75.55(13) . 3_566 ? C17 C16 Na1 90.40(13) . 3_566 ? C15 C16 Na1 104.54(13) . 3_566 ? O3 C17 C18 124.0(2) . . ? O3 C17 C16 115.2(2) . . ? C18 C17 C16 120.8(2) . . ? C19 C18 C17 119.6(2) . . ? C18 C19 C20 120.9(2) . . ? C19 C20 C21 118.6(2) . . ? C16 C21 C20 121.9(2) . . ? C16 C21 Na1 78.62(14) . 3_566 ? C20 C21 Na1 89.09(15) . 3_566 ? O4 C23 C24 106.1(2) . . ? C25 C24 C23 102.5(2) . . ? C26 C25 C24 102.6(2) . . ? O4 C26 C25 106.7(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.71 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.257 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.064 _chemical_compound_source 'Et2O and THF' #===END data_compound_8 _database_code_depnum_ccdc_archive 'CCDC 299158' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 387 _chemical_formula_moiety 'C52 H62 Na2 O10' _chemical_formula_sum 'C52 H62 Na2 O10' _chemical_formula_weight 893.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4333(2) _cell_length_b 11.0954(3) _cell_length_c 20.7892(5) _cell_angle_alpha 89.254(2) _cell_angle_beta 80.838(2) _cell_angle_gamma 83.6230(10) _cell_volume 2361.16(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21328 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.87 _reflns_number_total 9822 _reflns_number_gt 7271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0902P)^2^+1.8517P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9822 _refine_ls_number_parameters 585 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Na1 Na 0.38032(9) 0.59528(8) 0.01842(6) 0.0353(3) Uani 1 1 d . . . Na2 Na -0.58394(9) 0.90199(9) 0.52299(6) 0.0395(3) Uani 1 1 d . . . O1 O 0.40470(14) 0.39783(13) 0.00213(8) 0.0247(3) Uani 1 1 d . . . O2 O 0.54791(17) 0.52962(15) -0.20665(9) 0.0337(4) Uani 1 1 d . . . O3 O 0.41049(15) 0.06868(14) 0.13940(8) 0.0284(4) Uani 1 1 d . . . O4 O 0.32730(15) 0.79980(14) 0.04687(9) 0.0298(4) Uani 1 1 d . . . O5 O 0.17435(17) 0.61701(17) 0.08979(12) 0.0476(5) Uani 1 1 d . . . O6 O -0.36388(14) 0.90593(14) 0.50253(8) 0.0237(3) Uani 1 1 d . . . O7 O -0.42130(16) 1.21145(15) 0.65380(9) 0.0325(4) Uani 1 1 d . . . O8 O -0.20032(17) 0.54962(17) 0.32193(9) 0.0356(4) Uani 1 1 d . . . O9 O -0.79768(18) 0.84914(18) 0.54177(11) 0.0471(5) Uani 1 1 d . . . O10 O -0.57485(19) 0.68240(17) 0.52084(11) 0.0454(5) Uani 1 1 d . . . C1 C 0.32743(19) 0.32255(18) -0.01452(11) 0.0211(5) Uani 1 1 d . . . C2 C 0.3163(2) 0.30601(19) -0.08088(12) 0.0235(5) Uani 1 1 d . . . C3 C 0.2349(2) 0.22430(19) -0.09788(12) 0.0245(5) Uani 1 1 d . . . H3 H 0.2287 0.2136 -0.1425 0.029 Uiso 1 1 calc R . . C4 C 0.1628(2) 0.1583(2) -0.05088(12) 0.0252(5) Uani 1 1 d . . . H4 H 0.1079 0.1026 -0.0631 0.030 Uiso 1 1 calc R . . C5 C 0.1720(2) 0.17492(19) 0.01429(12) 0.0224(5) Uani 1 1 d . . . H5 H 0.1221 0.1304 0.0466 0.027 Uiso 1 1 calc R . . C6 C 0.2526(2) 0.25527(18) 0.03341(11) 0.0210(5) Uani 1 1 d . . . C7 C 0.3964(2) 0.3762(2) -0.13195(12) 0.0273(5) Uani 1 1 d . . . H7A H 0.3915 0.3427 -0.1753 0.033 Uiso 1 1 calc R . . H7B H 0.4888 0.3625 -0.1254 0.033 Uiso 1 1 calc R . . C8 C 0.3563(2) 0.5124(2) -0.13270(11) 0.0244(5) Uani 1 1 d . . . C9 C 0.4351(2) 0.5871(2) -0.17229(12) 0.0266(5) Uani 1 1 d . . . C10 C 0.3972(3) 0.7108(2) -0.17650(13) 0.0317(5) Uani 1 1 d . . . H10 H 0.4513 0.7608 -0.2035 0.038 Uiso 1 1 calc R . . C11 C 0.2793(3) 0.7608(2) -0.14076(13) 0.0346(6) Uani 1 1 d . . . H11 H 0.2525 0.8450 -0.1440 0.041 Uiso 1 1 calc R . . C12 C 0.2013(2) 0.6893(2) -0.10089(13) 0.0320(6) Uani 1 1 d . . . H12 H 0.1214 0.7238 -0.0763 0.038 Uiso 1 1 calc R . . C13 C 0.2408(2) 0.5654(2) -0.09694(12) 0.0260(5) Uani 1 1 d . . . H13 H 0.1872 0.5162 -0.0691 0.031 Uiso 1 1 calc R . . C14 C 0.6268(3) 0.6010(3) -0.25109(14) 0.0397(6) Uani 1 1 d . . . H14A H 0.5757 0.6367 -0.2837 0.060 Uiso 1 1 calc R . . H14B H 0.7033 0.5495 -0.2730 0.060 Uiso 1 1 calc R . . H14C H 0.6556 0.6659 -0.2271 0.060 Uiso 1 1 calc R . . C15 C 0.2671(2) 0.2759(2) 0.10369(11) 0.0241(5) Uani 1 1 d . . . H15A H 0.3614 0.2726 0.1064 0.029 Uiso 1 1 calc R . . H15B H 0.2264 0.3586 0.1169 0.029 Uiso 1 1 calc R . . C16 C 0.2077(2) 0.1867(2) 0.15170(11) 0.0238(5) Uani 1 1 d . . . C17 C 0.2827(2) 0.0811(2) 0.16850(11) 0.0229(5) Uani 1 1 d . . . C18 C 0.2270(2) -0.0028(2) 0.21149(12) 0.0277(5) Uani 1 1 d . . . H18 H 0.2790 -0.0731 0.2229 0.033 Uiso 1 1 calc R . . C19 C 0.0959(3) 0.0165(2) 0.23756(13) 0.0347(6) Uani 1 1 d . . . H19 H 0.0577 -0.0415 0.2664 0.042 Uiso 1 1 calc R . . C20 C 0.0200(2) 0.1197(3) 0.22191(13) 0.0383(6) Uani 1 1 d . . . H20 H -0.0701 0.1329 0.2398 0.046 Uiso 1 1 calc R . . C21 C 0.0773(2) 0.2040(2) 0.17965(13) 0.0319(5) Uani 1 1 d . . . H21 H 0.0253 0.2756 0.1697 0.038 Uiso 1 1 calc R . . C22 C 0.4921(3) -0.0356(2) 0.15485(14) 0.0370(6) Uani 1 1 d . . . H22A H 0.4949 -0.0366 0.2018 0.055 Uiso 1 1 calc R . . H22B H 0.5806 -0.0331 0.1308 0.055 Uiso 1 1 calc R . . H22C H 0.4571 -0.1088 0.1426 0.055 Uiso 1 1 calc R . . C23 C 0.3834(2) 0.8886(2) 0.00416(14) 0.0337(6) Uani 1 1 d . . . H23A H 0.3350 0.9017 -0.0325 0.051 Uiso 1 1 calc R . . H23B H 0.4749 0.8601 -0.0123 0.051 Uiso 1 1 calc R . . H23C H 0.3788 0.9650 0.0280 0.051 Uiso 1 1 calc R . . C24 C 0.1911(2) 0.8303(2) 0.06876(12) 0.0275(5) Uani 1 1 d . . . H24A H 0.1421 0.8304 0.0317 0.033 Uiso 1 1 calc R . . H24B H 0.1748 0.9119 0.0891 0.033 Uiso 1 1 calc R . . C25 C 0.1485(3) 0.7366(2) 0.11749(14) 0.0351(6) Uani 1 1 d . . . H25A H 0.1952 0.7403 0.1552 0.042 Uiso 1 1 calc R . . H25B H 0.0538 0.7544 0.1335 0.042 Uiso 1 1 calc R . . C26 C 0.0639(2) 0.5680(2) 0.07554(14) 0.0362(6) Uani 1 1 d . . . H26A H 0.0019 0.5612 0.1158 0.054 Uiso 1 1 calc R . . H26B H 0.0901 0.4875 0.0559 0.054 Uiso 1 1 calc R . . H26C H 0.0223 0.6211 0.0450 0.054 Uiso 1 1 calc R . . C27 C -0.29017(19) 0.82862(19) 0.53290(11) 0.0210(4) Uani 1 1 d . . . C28 C -0.2642(2) 0.8558(2) 0.59629(11) 0.0226(5) Uani 1 1 d . . . C29 C -0.1968(2) 0.7700(2) 0.63097(12) 0.0264(5) Uani 1 1 d . . . H29 H -0.1834 0.7893 0.6736 0.032 Uiso 1 1 calc R . . C30 C -0.1480(2) 0.6558(2) 0.60474(12) 0.0296(5) Uani 1 1 d . . . H30 H -0.1049 0.5964 0.6296 0.035 Uiso 1 1 calc R . . C31 C -0.1643(2) 0.6314(2) 0.54133(12) 0.0271(5) Uani 1 1 d . . . H31 H -0.1278 0.5554 0.5222 0.032 Uiso 1 1 calc R . . C32 C -0.2323(2) 0.7144(2) 0.50491(11) 0.0232(5) Uani 1 1 d . . . C33 C -0.3088(2) 0.9812(2) 0.62310(12) 0.0243(5) Uani 1 1 d . . . H33A H -0.2890 1.0401 0.5877 0.029 Uiso 1 1 calc R . . H33B H -0.2565 0.9965 0.6573 0.029 Uiso 1 1 calc R . . C34 C -0.4520(2) 1.0061(2) 0.65171(11) 0.0236(5) Uani 1 1 d . . . C35 C -0.5065(2) 1.1254(2) 0.66749(11) 0.0253(5) Uani 1 1 d . . . C36 C -0.6365(2) 1.1510(2) 0.69586(12) 0.0290(5) Uani 1 1 d . . . H36 H -0.6716 1.2321 0.7070 0.035 Uiso 1 1 calc R . . C37 C -0.7148(2) 1.0570(2) 0.70785(13) 0.0338(6) Uani 1 1 d . . . H37 H -0.8040 1.0740 0.7267 0.041 Uiso 1 1 calc R . . C38 C -0.6633(2) 0.9393(2) 0.69247(14) 0.0362(6) Uani 1 1 d . . . H38 H -0.7168 0.8752 0.7008 0.043 Uiso 1 1 calc R . . C39 C -0.5321(2) 0.9144(2) 0.66463(12) 0.0289(5) Uani 1 1 d . . . H39 H -0.4972 0.8329 0.6544 0.035 Uiso 1 1 calc R . . C40 C -0.4691(3) 1.3343(2) 0.67043(14) 0.0355(6) Uani 1 1 d . . . H40A H -0.5442 1.3595 0.6485 0.053 Uiso 1 1 calc R . . H40B H -0.3999 1.3864 0.6565 0.053 Uiso 1 1 calc R . . H40C H -0.4960 1.3415 0.7177 0.053 Uiso 1 1 calc R . . C41 C -0.2442(2) 0.6856(2) 0.43557(12) 0.0266(5) Uani 1 1 d . . . H41A H -0.3081 0.7478 0.4204 0.032 Uiso 1 1 calc R . . H41B H -0.2790 0.6063 0.4346 0.032 Uiso 1 1 calc R . . C42 C -0.1165(2) 0.6807(2) 0.38859(12) 0.0253(5) Uani 1 1 d . . . C43 C -0.0978(2) 0.6128(2) 0.33072(12) 0.0279(5) Uani 1 1 d . . . C44 C 0.0176(3) 0.6106(3) 0.28657(13) 0.0360(6) Uani 1 1 d . . . H44 H 0.0289 0.5643 0.2476 0.043 Uiso 1 1 calc R . . C45 C 0.1160(3) 0.6765(3) 0.29968(14) 0.0394(6) Uani 1 1 d . . . H45 H 0.1941 0.6763 0.2691 0.047 Uiso 1 1 calc R . . C46 C 0.1015(3) 0.7419(2) 0.35641(14) 0.0375(6) Uani 1 1 d . . . H46 H 0.1699 0.7853 0.3658 0.045 Uiso 1 1 calc R . . C47 C -0.0145(2) 0.7437(2) 0.40005(13) 0.0315(5) Uani 1 1 d . . . H47 H -0.0244 0.7898 0.4391 0.038 Uiso 1 1 calc R . . C48 C -0.1807(3) 0.4693(3) 0.26722(17) 0.0577(9) Uani 1 1 d . . . H48A H -0.1694 0.5164 0.2269 0.087 Uiso 1 1 calc R . . H48B H -0.2567 0.4243 0.2687 0.087 Uiso 1 1 calc R . . H48C H -0.1024 0.4123 0.2686 0.087 Uiso 1 1 calc R . . C49 C -0.9050(3) 0.9243(4) 0.5755(2) 0.0704(11) Uani 1 1 d . . . H49A H -0.9835 0.9145 0.5567 0.106 Uiso 1 1 calc R . . H49B H -0.8869 1.0091 0.5717 0.106 Uiso 1 1 calc R . . H49C H -0.9188 0.9014 0.6216 0.106 Uiso 1 1 calc R . . C50 C -0.8114(3) 0.7227(3) 0.54645(16) 0.0463(7) Uani 1 1 d . . . H50A H -0.8937 0.7059 0.5321 0.056 Uiso 1 1 calc R . . H50B H -0.8130 0.6952 0.5920 0.056 Uiso 1 1 calc R . . C51 C -0.6963(3) 0.6582(3) 0.50320(18) 0.0515(8) Uani 1 1 d . . . H51A H -0.7023 0.5698 0.5056 0.062 Uiso 1 1 calc R . . H51B H -0.6989 0.6838 0.4576 0.062 Uiso 1 1 calc R . . C52 C -0.5380(3) 0.6113(3) 0.57365(16) 0.0426(7) Uani 1 1 d . . . H52A H -0.6002 0.6331 0.6133 0.064 Uiso 1 1 calc R . . H52B H -0.4503 0.6266 0.5802 0.064 Uiso 1 1 calc R . . H52C H -0.5381 0.5252 0.5638 0.064 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 Na1 0.0202(4) 0.0216(5) 0.0619(7) -0.0076(4) 0.0005(4) -0.0016(4) Na2 0.0254(5) 0.0264(5) 0.0681(8) 0.0172(5) -0.0101(5) -0.0072(4) O1 0.0211(7) 0.0191(7) 0.0334(9) 0.0003(6) -0.0017(6) -0.0037(6) O2 0.0359(9) 0.0303(9) 0.0320(10) 0.0011(7) 0.0078(8) -0.0095(7) O3 0.0248(8) 0.0255(8) 0.0320(10) 0.0045(7) -0.0008(7) 0.0046(6) O4 0.0240(8) 0.0214(8) 0.0418(11) 0.0025(7) -0.0003(7) -0.0006(6) O5 0.0267(9) 0.0289(9) 0.0829(16) -0.0115(10) 0.0065(9) -0.0049(7) O6 0.0226(7) 0.0241(8) 0.0246(9) 0.0019(6) -0.0049(6) -0.0016(6) O7 0.0276(8) 0.0269(9) 0.0408(11) -0.0026(7) 0.0025(7) -0.0051(7) O8 0.0321(9) 0.0422(10) 0.0323(10) -0.0137(8) -0.0053(7) -0.0016(8) O9 0.0306(10) 0.0390(11) 0.0686(15) 0.0001(10) 0.0063(9) -0.0108(8) O10 0.0416(11) 0.0332(10) 0.0626(14) 0.0066(9) -0.0106(10) -0.0068(8) C1 0.0149(9) 0.0160(10) 0.0304(13) -0.0015(8) -0.0007(8) 0.0032(7) C2 0.0199(10) 0.0178(10) 0.0300(13) -0.0007(9) 0.0012(9) 0.0032(8) C3 0.0241(11) 0.0211(11) 0.0268(13) -0.0023(9) -0.0030(9) 0.0027(8) C4 0.0188(10) 0.0194(10) 0.0376(14) -0.0017(9) -0.0052(9) -0.0018(8) C5 0.0177(9) 0.0164(10) 0.0314(13) 0.0029(9) -0.0011(9) 0.0005(8) C6 0.0177(9) 0.0162(10) 0.0277(13) -0.0003(8) -0.0032(8) 0.0036(8) C7 0.0272(11) 0.0239(11) 0.0281(13) -0.0010(9) 0.0034(10) -0.0018(9) C8 0.0267(11) 0.0243(11) 0.0230(12) 0.0011(9) -0.0045(9) -0.0047(9) C9 0.0289(11) 0.0269(12) 0.0250(13) 0.0000(9) -0.0043(9) -0.0070(9) C10 0.0427(14) 0.0248(12) 0.0298(14) 0.0049(10) -0.0084(11) -0.0106(10) C11 0.0465(15) 0.0220(12) 0.0370(15) 0.0024(10) -0.0157(12) 0.0011(10) C12 0.0314(12) 0.0291(12) 0.0352(15) -0.0038(10) -0.0106(10) 0.0050(10) C13 0.0256(11) 0.0267(11) 0.0259(13) 0.0025(9) -0.0056(9) -0.0019(9) C14 0.0437(15) 0.0397(15) 0.0350(16) 0.0017(12) 0.0056(12) -0.0181(12) C15 0.0235(10) 0.0207(10) 0.0276(13) 0.0010(9) -0.0043(9) 0.0000(8) C16 0.0233(10) 0.0243(11) 0.0235(12) -0.0018(9) -0.0044(9) -0.0003(8) C17 0.0245(10) 0.0231(11) 0.0204(12) -0.0031(9) -0.0017(9) -0.0016(8) C18 0.0358(12) 0.0247(11) 0.0240(13) 0.0010(9) -0.0075(10) -0.0054(9) C19 0.0402(14) 0.0424(15) 0.0238(13) 0.0059(11) -0.0039(11) -0.0161(11) C20 0.0235(12) 0.0591(18) 0.0312(15) 0.0018(12) 0.0012(10) -0.0077(11) C21 0.0242(11) 0.0373(13) 0.0321(14) 0.0016(11) -0.0032(10) 0.0039(10) C22 0.0334(13) 0.0353(14) 0.0383(16) 0.0045(11) -0.0048(11) 0.0120(11) C23 0.0335(13) 0.0254(12) 0.0397(15) 0.0016(11) 0.0022(11) -0.0038(10) C24 0.0244(11) 0.0264(11) 0.0299(13) -0.0058(10) -0.0021(9) 0.0018(9) C25 0.0332(13) 0.0293(13) 0.0395(16) -0.0033(11) 0.0047(11) -0.0039(10) C26 0.0251(12) 0.0328(13) 0.0484(17) -0.0023(12) -0.0004(11) -0.0006(10) C27 0.0149(9) 0.0235(11) 0.0242(12) 0.0050(9) -0.0007(8) -0.0048(8) C28 0.0173(9) 0.0274(11) 0.0227(12) 0.0005(9) -0.0002(8) -0.0051(8) C29 0.0203(10) 0.0368(13) 0.0215(12) 0.0044(9) -0.0009(9) -0.0052(9) C30 0.0238(11) 0.0333(13) 0.0306(14) 0.0095(10) -0.0037(10) -0.0005(9) C31 0.0218(10) 0.0234(11) 0.0349(14) 0.0017(10) -0.0020(9) -0.0013(8) C32 0.0165(9) 0.0266(11) 0.0260(12) 0.0006(9) -0.0014(8) -0.0037(8) C33 0.0222(10) 0.0275(11) 0.0229(12) -0.0003(9) -0.0004(9) -0.0055(9) C34 0.0213(10) 0.0321(12) 0.0173(11) 0.0005(9) -0.0029(8) -0.0035(9) C35 0.0268(11) 0.0300(12) 0.0194(12) 0.0013(9) -0.0033(9) -0.0054(9) C36 0.0265(11) 0.0326(12) 0.0261(13) 0.0013(10) -0.0024(9) 0.0023(9) C37 0.0217(11) 0.0410(14) 0.0362(15) 0.0049(11) 0.0016(10) -0.0024(10) C38 0.0264(12) 0.0384(14) 0.0431(16) 0.0066(12) 0.0019(11) -0.0117(10) C39 0.0292(12) 0.0286(12) 0.0284(13) 0.0025(10) -0.0015(10) -0.0061(9) C40 0.0345(13) 0.0268(12) 0.0444(16) -0.0049(11) -0.0030(11) -0.0043(10) C41 0.0215(10) 0.0286(12) 0.0295(13) -0.0053(10) -0.0027(9) -0.0029(9) C42 0.0250(11) 0.0244(11) 0.0260(13) 0.0032(9) -0.0048(9) 0.0002(9) C43 0.0257(11) 0.0289(12) 0.0281(13) 0.0009(10) -0.0054(9) 0.0023(9) C44 0.0342(13) 0.0451(15) 0.0263(14) 0.0008(11) -0.0039(10) 0.0050(11) C45 0.0295(13) 0.0523(17) 0.0330(16) 0.0139(12) 0.0019(11) -0.0015(12) C46 0.0315(13) 0.0387(14) 0.0438(17) 0.0116(12) -0.0057(11) -0.0119(11) C47 0.0315(12) 0.0292(12) 0.0332(14) 0.0008(10) -0.0035(10) -0.0038(10) C48 0.0523(18) 0.075(2) 0.048(2) -0.0323(17) -0.0079(15) -0.0099(16) C49 0.0327(16) 0.082(3) 0.091(3) -0.022(2) 0.0031(17) 0.0019(16) C50 0.0419(15) 0.0492(17) 0.0538(19) 0.0140(14) -0.0113(14) -0.0273(13) C51 0.0537(18) 0.0364(15) 0.069(2) -0.0014(15) -0.0200(16) -0.0094(13) C52 0.0407(15) 0.0333(14) 0.0557(19) 0.0088(13) -0.0117(13) -0.0075(11) _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 Na1 O1 2.2016(17) . ? Na1 O1 2.2252(17) 2_665 ? Na1 O4 2.3361(18) . ? Na1 O5 2.399(2) . ? Na1 C13 3.037(3) . ? Na1 Na1 3.0909(18) 2_665 ? Na2 O6 2.2192(18) 2_476 ? Na2 O6 2.2727(18) . ? Na2 O9 2.340(2) . ? Na2 O10 2.428(2) . ? Na2 Na2 2.9951(19) 2_476 ? Na2 C39 3.085(3) . ? Na2 C51 3.122(3) . ? O1 C1 1.309(3) . ? O1 Na1 2.2252(17) 2_665 ? O2 C9 1.371(3) . ? O2 C14 1.429(3) . ? O3 C17 1.367(3) . ? O3 C22 1.423(3) . ? O4 C24 1.426(3) . ? O4 C23 1.429(3) . ? O5 C26 1.401(3) . ? O5 C25 1.434(3) . ? O6 C27 1.311(3) . ? O6 Na2 2.2192(18) 2_476 ? O7 C35 1.372(3) . ? O7 C40 1.426(3) . ? O8 C43 1.378(3) . ? O8 C48 1.429(3) . ? O9 C49 1.414(4) . ? O9 C50 1.427(4) . ? O10 C52 1.421(4) . ? O10 C51 1.427(4) . ? C1 C2 1.419(3) . ? C1 C6 1.422(3) . ? C2 C3 1.394(3) . ? C2 C7 1.508(3) . ? C3 C4 1.388(3) . ? C4 C5 1.389(3) . ? C5 C6 1.393(3) . ? C6 C15 1.516(3) . ? C7 C8 1.523(3) . ? C8 C13 1.386(3) . ? C8 C9 1.399(3) . ? C9 C10 1.391(3) . ? C10 C11 1.394(4) . ? C11 C12 1.375(4) . ? C12 C13 1.396(3) . ? C15 C16 1.508(3) . ? C16 C21 1.385(3) . ? C16 C17 1.407(3) . ? C17 C18 1.391(3) . ? C18 C19 1.383(4) . ? C19 C20 1.383(4) . ? C20 C21 1.393(4) . ? C24 C25 1.495(4) . ? C27 C28 1.430(3) . ? C27 C32 1.430(3) . ? C28 C29 1.384(3) . ? C28 C33 1.501(3) . ? C29 C30 1.396(3) . ? C30 C31 1.390(4) . ? C31 C32 1.390(3) . ? C32 C41 1.508(3) . ? C33 C34 1.514(3) . ? C34 C39 1.384(3) . ? C34 C35 1.403(3) . ? C35 C36 1.390(3) . ? C36 C37 1.391(4) . ? C37 C38 1.377(4) . ? C38 C39 1.397(3) . ? C41 C42 1.517(3) . ? C42 C47 1.388(3) . ? C42 C43 1.404(3) . ? C43 C44 1.391(4) . ? C44 C45 1.387(4) . ? C45 C46 1.372(4) . ? C46 C47 1.391(4) . ? C50 C51 1.498(5) . ? 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 O1 Na1 O1 91.43(6) . 2_665 ? O1 Na1 O4 171.52(8) . . ? O1 Na1 O4 95.77(6) 2_665 . ? O1 Na1 O5 99.98(7) . . ? O1 Na1 O5 152.08(9) 2_665 . ? O4 Na1 O5 71.60(6) . . ? O1 Na1 C13 76.47(7) . . ? O1 Na1 C13 117.49(7) 2_665 . ? O4 Na1 C13 103.97(7) . . ? O5 Na1 C13 90.06(8) . . ? O1 Na1 Na1 46.03(5) . 2_665 ? O1 Na1 Na1 45.40(4) 2_665 2_665 ? O4 Na1 Na1 140.97(7) . 2_665 ? O5 Na1 Na1 139.42(8) . 2_665 ? C13 Na1 Na1 99.53(6) . 2_665 ? O6 Na2 O6 96.37(6) 2_476 . ? O6 Na2 O9 96.25(7) 2_476 . ? O6 Na2 O9 166.65(8) . . ? O6 Na2 O10 159.24(8) 2_476 . ? O6 Na2 O10 95.20(7) . . ? O9 Na2 O10 71.46(7) . . ? O6 Na2 Na2 48.95(5) 2_476 2_476 ? O6 Na2 Na2 47.42(5) . 2_476 ? O9 Na2 Na2 144.99(8) . 2_476 ? O10 Na2 Na2 139.60(8) . 2_476 ? O6 Na2 C39 104.08(7) 2_476 . ? O6 Na2 C39 81.19(7) . . ? O9 Na2 C39 99.89(8) . . ? O10 Na2 C39 94.69(8) . . ? Na2 Na2 C39 93.67(7) 2_476 . ? O6 Na2 C51 134.78(8) 2_476 . ? O6 Na2 C51 118.51(8) . . ? O9 Na2 C51 48.42(8) . . ? O10 Na2 C51 26.20(8) . . ? Na2 Na2 C51 152.13(10) 2_476 . ? C39 Na2 C51 108.70(9) . . ? C1 O1 Na1 132.78(13) . . ? C1 O1 Na1 133.47(13) . 2_665 ? Na1 O1 Na1 88.57(6) . 2_665 ? C9 O2 C14 117.4(2) . . ? C17 O3 C22 117.93(19) . . ? C24 O4 C23 112.83(18) . . ? C24 O4 Na1 112.72(13) . . ? C23 O4 Na1 118.43(14) . . ? C26 O5 C25 114.61(19) . . ? C26 O5 Na1 122.83(17) . . ? C25 O5 Na1 110.34(14) . . ? C27 O6 Na2 147.12(14) . 2_476 ? C27 O6 Na2 118.64(13) . . ? Na2 O6 Na2 83.63(6) 2_476 . ? C35 O7 C40 117.81(18) . . ? C43 O8 C48 117.3(2) . . ? C49 O9 C50 114.2(3) . . ? C49 O9 Na2 123.5(2) . . ? C50 O9 Na2 116.41(17) . . ? C52 O10 C51 113.9(2) . . ? C52 O10 Na2 120.98(17) . . ? C51 O10 Na2 105.12(16) . . ? O1 C1 C2 120.8(2) . . ? O1 C1 C6 120.9(2) . . ? C2 C1 C6 118.3(2) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 C7 121.3(2) . . ? C1 C2 C7 118.5(2) . . ? C4 C3 C2 121.3(2) . . ? C3 C4 C5 119.0(2) . . ? C4 C5 C6 121.6(2) . . ? C5 C6 C1 119.7(2) . . ? C5 C6 C15 123.7(2) . . ? C1 C6 C15 116.58(19) . . ? C2 C7 C8 115.70(18) . . ? C13 C8 C9 118.1(2) . . ? C13 C8 C7 122.0(2) . . ? C9 C8 C7 119.8(2) . . ? O2 C9 C10 123.5(2) . . ? O2 C9 C8 115.5(2) . . ? C10 C9 C8 120.9(2) . . ? C9 C10 C11 119.4(2) . . ? C12 C11 C10 120.6(2) . . ? C11 C12 C13 119.3(2) . . ? C8 C13 C12 121.6(2) . . ? C8 C13 Na1 90.10(14) . . ? C12 C13 Na1 93.62(15) . . ? C16 C15 C6 115.08(19) . . ? C21 C16 C17 117.6(2) . . ? C21 C16 C15 121.5(2) . . ? C17 C16 C15 120.87(19) . . ? O3 C17 C18 124.0(2) . . ? O3 C17 C16 115.1(2) . . ? C18 C17 C16 120.9(2) . . ? C19 C18 C17 119.9(2) . . ? C18 C19 C20 120.4(2) . . ? C19 C20 C21 119.2(2) . . ? C16 C21 C20 122.0(2) . . ? O4 C24 C25 107.02(19) . . ? O5 C25 C24 111.5(2) . . ? O6 C27 C28 120.72(19) . . ? O6 C27 C32 122.3(2) . . ? C28 C27 C32 116.9(2) . . ? C29 C28 C27 120.8(2) . . ? C29 C28 C33 121.2(2) . . ? C27 C28 C33 118.0(2) . . ? C28 C29 C30 121.6(2) . . ? C31 C30 C29 118.2(2) . . ? C30 C31 C32 122.2(2) . . ? C31 C32 C27 120.0(2) . . ? C31 C32 C41 120.4(2) . . ? C27 C32 C41 119.6(2) . . ? C28 C33 C34 116.14(18) . . ? C39 C34 C35 118.0(2) . . ? C39 C34 C33 122.3(2) . . ? C35 C34 C33 119.7(2) . . ? O7 C35 C36 124.0(2) . . ? O7 C35 C34 114.80(19) . . ? C36 C35 C34 121.2(2) . . ? C35 C36 C37 119.5(2) . . ? C38 C37 C36 120.2(2) . . ? C37 C38 C39 119.9(2) . . ? C34 C39 C38 121.3(2) . . ? C34 C39 Na2 93.78(15) . . ? C38 C39 Na2 95.56(17) . . ? C32 C41 C42 114.07(19) . . ? C47 C42 C43 117.2(2) . . ? C47 C42 C41 122.1(2) . . ? C43 C42 C41 120.7(2) . . ? O8 C43 C44 123.7(2) . . ? O8 C43 C42 115.3(2) . . ? C44 C43 C42 121.0(2) . . ? C45 C44 C43 119.8(2) . . ? C46 C45 C44 120.5(2) . . ? C45 C46 C47 119.2(2) . . ? C42 C47 C46 122.3(2) . . ? O9 C50 C51 106.9(2) . . ? O10 C51 C50 112.5(3) . . ? O10 C51 Na2 48.68(12) . . ? C50 C51 Na2 80.74(16) . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.988 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.060 _chemical_compound_source DME #===END data_COMPOUND_9 _database_code_depnum_ccdc_archive 'CCDC 299159' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C68 H84 Na4 O12' _chemical_formula_sum 'C68 H84 Na4 O12' _chemical_formula_weight 1185.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_int_tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 20.2800(5) _cell_length_b 15.0904(3) _cell_length_c 21.4779(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6573.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'trapezoidal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34697 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.1001 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.29 _reflns_number_total 8106 _reflns_number_gt 3912 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0906P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8106 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _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 Na1 Na 0.05686(3) 0.85371(5) 0.30642(3) 0.0258(2) Uani 1 1 d . . . Na2 Na 0.05211(3) 0.70402(5) 0.18999(3) 0.0261(2) Uani 1 1 d . . . O1 O 0.06308(6) 0.70216(8) 0.29902(6) 0.0267(3) Uani 1 1 d . . . O2 O 0.05792(6) 0.85629(8) 0.19686(6) 0.0274(3) Uani 1 1 d . . . O3 O 0.13827(6) 0.96065(9) 0.33307(6) 0.0335(4) Uani 1 1 d . . . O4 O 0.05561(6) 0.88798(9) 0.42045(6) 0.0323(3) Uani 1 1 d . . . O5 O 0.13564(6) 0.60054(9) 0.16431(6) 0.0336(4) Uani 1 1 d . . . O6 O 0.04770(6) 0.65324(9) 0.07348(6) 0.0327(4) Uani 1 1 d . . . C1 C 0.09157(9) 0.63573(12) 0.32856(9) 0.0251(5) Uani 1 1 d . . . C2 C 0.15154(9) 0.64693(12) 0.36174(9) 0.0259(5) Uani 1 1 d . . . C3 C 0.17774(10) 0.57597(13) 0.39478(10) 0.0326(5) Uani 1 1 d . . . H3 H 0.2171 0.5845 0.4180 0.039 Uiso 1 1 calc R . . C4 C 0.14827(10) 0.49314(14) 0.39487(10) 0.0378(5) Uani 1 1 d . . . H4 H 0.1667 0.4459 0.4184 0.045 Uiso 1 1 calc R . . C5 C 0.09191(11) 0.48034(14) 0.36047(11) 0.0395(6) Uani 1 1 d . . . H5 H 0.0721 0.4233 0.3590 0.047 Uiso 1 1 calc R . . C6 C 0.06364(10) 0.55002(13) 0.32785(10) 0.0329(5) Uani 1 1 d . . . H6 H 0.0246 0.5398 0.3045 0.039 Uiso 1 1 calc R . . C7 C 0.18526(9) 0.73659(13) 0.35929(11) 0.0350(5) Uani 1 1 d . . . H7A H 0.1783 0.7624 0.3174 0.042 Uiso 1 1 calc R . . H7B H 0.1637 0.7763 0.3898 0.042 Uiso 1 1 calc R . . C8 C 0.25849(10) 0.73523(13) 0.37256(10) 0.0339(5) Uani 1 1 d . . . C9 C 0.30282(11) 0.70824(14) 0.32708(11) 0.0409(6) Uani 1 1 d . . . H9 H 0.2868 0.6930 0.2869 0.049 Uiso 1 1 calc R . . C10 C 0.36988(11) 0.70300(15) 0.33907(12) 0.0469(6) Uani 1 1 d . . . H10 H 0.3993 0.6843 0.3072 0.056 Uiso 1 1 calc R . . C11 C 0.39408(12) 0.72496(15) 0.39722(12) 0.0470(6) Uani 1 1 d . . . H11 H 0.4399 0.7206 0.4058 0.056 Uiso 1 1 calc R . . C12 C 0.35151(12) 0.75288(15) 0.44200(12) 0.0455(6) Uani 1 1 d . . . H12 H 0.3678 0.7683 0.4820 0.055 Uiso 1 1 calc R . . C13 C 0.28422(11) 0.75915(14) 0.42983(11) 0.0405(6) Uani 1 1 d . . . H13 H 0.2554 0.7802 0.4614 0.049 Uiso 1 1 calc R . . C14 C 0.08456(9) 0.92646(13) 0.16994(9) 0.0268(5) Uani 1 1 d . . . C15 C 0.14517(9) 0.92033(13) 0.13797(9) 0.0303(5) Uani 1 1 d . . . C16 C 0.17043(10) 0.99548(14) 0.10778(10) 0.0366(5) Uani 1 1 d . . . H16 H 0.2104 0.9904 0.0850 0.044 Uiso 1 1 calc R . . C17 C 0.13892(11) 1.07657(15) 0.11023(11) 0.0427(6) Uani 1 1 d . . . H17 H 0.1570 1.1266 0.0895 0.051 Uiso 1 1 calc R . . C18 C 0.08100(11) 1.08364(14) 0.14318(11) 0.0409(6) Uani 1 1 d . . . H18 H 0.0593 1.1393 0.1459 0.049 Uiso 1 1 calc R . . C19 C 0.05413(10) 1.01063(13) 0.17238(9) 0.0334(5) Uani 1 1 d . . . H19 H 0.0140 1.0171 0.1948 0.040 Uiso 1 1 calc R . . C20 C 0.17931(10) 0.83191(14) 0.13791(11) 0.0421(6) Uani 1 1 d . . . H20A H 0.1598 0.7952 0.1045 0.051 Uiso 1 1 calc R . . H20B H 0.1698 0.8021 0.1780 0.051 Uiso 1 1 calc R . . C21 C 0.25355(10) 0.83368(14) 0.12874(10) 0.0358(5) Uani 1 1 d . . . C22 C 0.29577(11) 0.83577(15) 0.17906(11) 0.0437(6) Uani 1 1 d . . . H22 H 0.2781 0.8361 0.2200 0.052 Uiso 1 1 calc R . . C23 C 0.36320(12) 0.83739(17) 0.17103(12) 0.0530(7) Uani 1 1 d . . . H23 H 0.3914 0.8393 0.2063 0.064 Uiso 1 1 calc R . . C24 C 0.38979(12) 0.83624(15) 0.11216(13) 0.0523(7) Uani 1 1 d . . . H24 H 0.4363 0.8362 0.1066 0.063 Uiso 1 1 calc R . . C25 C 0.34875(12) 0.83507(16) 0.06154(12) 0.0514(7) Uani 1 1 d . . . H25 H 0.3667 0.8347 0.0207 0.062 Uiso 1 1 calc R . . C26 C 0.28106(11) 0.83451(15) 0.06983(11) 0.0442(6) Uani 1 1 d . . . H26 H 0.2530 0.8347 0.0344 0.053 Uiso 1 1 calc R . . C27 C 0.19704(10) 0.96823(15) 0.29720(10) 0.0425(6) Uani 1 1 d . . . H27A H 0.2164 1.0271 0.3035 0.064 Uiso 1 1 calc R . . H27B H 0.1866 0.9601 0.2530 0.064 Uiso 1 1 calc R . . H27C H 0.2286 0.9228 0.3104 0.064 Uiso 1 1 calc R . . C28 C 0.15123(10) 0.97394(14) 0.39752(10) 0.0339(5) Uani 1 1 d . . . H28A H 0.1726 1.0322 0.4039 0.041 Uiso 1 1 calc R . . H28B H 0.1814 0.9273 0.4130 0.041 Uiso 1 1 calc R . . C29 C 0.08758(10) 0.97048(13) 0.43227(9) 0.0332(5) Uani 1 1 d . . . H29A H 0.0960 0.9769 0.4774 0.040 Uiso 1 1 calc R . . H29B H 0.0588 1.0199 0.4189 0.040 Uiso 1 1 calc R . . C30 C -0.00310(10) 0.88074(15) 0.45703(10) 0.0383(5) Uani 1 1 d . . . H30A H 0.0087 0.8761 0.5012 0.057 Uiso 1 1 calc R . . H30B H -0.0277 0.8278 0.4444 0.057 Uiso 1 1 calc R . . H30C H -0.0305 0.9334 0.4506 0.057 Uiso 1 1 calc R . . C31 C 0.19443(10) 0.59318(16) 0.20019(10) 0.0432(6) Uani 1 1 d . . . H31A H 0.2112 0.5324 0.1977 0.065 Uiso 1 1 calc R . . H31B H 0.1849 0.6079 0.2437 0.065 Uiso 1 1 calc R . . H31C H 0.2277 0.6342 0.1839 0.065 Uiso 1 1 calc R . . C32 C 0.14716(9) 0.57954(14) 0.10092(10) 0.0349(5) Uani 1 1 d . . . H32A H 0.1716 0.5229 0.0978 0.042 Uiso 1 1 calc R . . H32B H 0.1741 0.6266 0.0813 0.042 Uiso 1 1 calc R . . C33 C 0.08255(10) 0.57174(14) 0.06800(10) 0.0352(5) Uani 1 1 d . . . H33A H 0.0900 0.5578 0.0235 0.042 Uiso 1 1 calc R . . H33B H 0.0563 0.5232 0.0866 0.042 Uiso 1 1 calc R . . C34 C -0.01111(10) 0.65118(16) 0.03661(10) 0.0415(6) Uani 1 1 d . . . H34A H 0.0007 0.6499 -0.0076 0.062 Uiso 1 1 calc R . . H34B H -0.0376 0.7041 0.0453 0.062 Uiso 1 1 calc R . . H34C H -0.0367 0.5981 0.0469 0.062 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 Na1 0.0216(4) 0.0275(4) 0.0282(4) -0.0022(3) 0.0013(3) -0.0026(3) Na2 0.0223(4) 0.0284(4) 0.0276(4) -0.0020(3) 0.0026(3) 0.0032(3) O1 0.0257(7) 0.0273(7) 0.0271(8) 0.0027(6) -0.0018(6) 0.0020(6) O2 0.0226(7) 0.0300(7) 0.0295(8) 0.0047(6) 0.0037(6) -0.0027(6) O3 0.0282(8) 0.0433(9) 0.0289(8) -0.0051(7) 0.0013(6) -0.0082(6) O4 0.0317(8) 0.0359(8) 0.0294(8) -0.0061(6) 0.0060(6) -0.0035(6) O5 0.0272(8) 0.0469(9) 0.0268(8) -0.0065(7) -0.0018(6) 0.0120(7) O6 0.0268(7) 0.0379(8) 0.0335(8) -0.0006(7) -0.0071(6) 0.0021(6) C1 0.0268(11) 0.0262(11) 0.0221(10) -0.0004(9) 0.0064(9) 0.0016(9) C2 0.0236(10) 0.0272(11) 0.0269(11) 0.0008(9) 0.0051(9) 0.0036(9) C3 0.0280(11) 0.0365(12) 0.0331(12) 0.0064(10) 0.0036(10) 0.0069(10) C4 0.0356(12) 0.0317(12) 0.0462(14) 0.0134(11) 0.0106(11) 0.0121(10) C5 0.0413(13) 0.0262(12) 0.0510(15) 0.0028(11) 0.0093(12) -0.0028(10) C6 0.0307(12) 0.0304(12) 0.0376(13) -0.0014(10) 0.0028(10) -0.0001(10) C7 0.0309(12) 0.0297(12) 0.0443(14) 0.0005(10) -0.0061(10) 0.0028(10) C8 0.0323(12) 0.0275(11) 0.0419(14) 0.0057(10) -0.0050(11) -0.0010(10) C9 0.0380(13) 0.0449(14) 0.0398(14) 0.0088(11) -0.0042(11) -0.0014(11) C10 0.0326(14) 0.0522(15) 0.0559(17) 0.0090(13) 0.0064(12) -0.0018(11) C11 0.0359(13) 0.0404(14) 0.0646(18) 0.0131(13) -0.0133(13) -0.0068(11) C12 0.0470(15) 0.0416(14) 0.0479(15) 0.0053(12) -0.0171(13) -0.0044(12) C13 0.0433(14) 0.0349(13) 0.0432(14) 0.0008(11) -0.0043(11) -0.0005(11) C14 0.0257(11) 0.0313(12) 0.0234(11) 0.0007(9) -0.0050(9) -0.0058(9) C15 0.0245(11) 0.0348(12) 0.0316(12) 0.0024(10) 0.0005(9) -0.0031(10) C16 0.0257(11) 0.0473(14) 0.0368(13) 0.0073(11) 0.0000(10) -0.0099(11) C17 0.0394(13) 0.0374(13) 0.0512(15) 0.0161(11) -0.0114(12) -0.0108(11) C18 0.0375(13) 0.0324(12) 0.0528(15) 0.0044(11) -0.0102(12) 0.0002(11) C19 0.0311(12) 0.0335(12) 0.0356(12) -0.0006(10) -0.0006(10) -0.0028(10) C20 0.0326(12) 0.0374(13) 0.0563(16) 0.0028(12) 0.0126(11) -0.0061(11) C21 0.0307(12) 0.0331(12) 0.0436(14) 0.0018(10) 0.0099(11) -0.0017(10) C22 0.0447(14) 0.0481(14) 0.0383(14) 0.0076(11) 0.0047(12) 0.0080(12) C23 0.0375(14) 0.0623(17) 0.0591(18) 0.0098(14) -0.0068(13) 0.0059(13) C24 0.0318(13) 0.0485(15) 0.077(2) 0.0126(14) 0.0131(14) 0.0044(11) C25 0.0463(15) 0.0586(16) 0.0491(16) 0.0011(13) 0.0222(13) 0.0045(13) C26 0.0399(14) 0.0520(15) 0.0406(14) -0.0083(12) 0.0085(11) -0.0012(11) C27 0.0345(13) 0.0552(15) 0.0379(14) -0.0061(11) 0.0069(11) -0.0166(11) C28 0.0336(12) 0.0350(12) 0.0331(12) -0.0079(10) -0.0071(10) -0.0040(10) C29 0.0346(12) 0.0345(12) 0.0305(12) -0.0080(9) 0.0002(10) -0.0021(10) C30 0.0376(13) 0.0474(13) 0.0298(12) -0.0004(10) 0.0076(10) -0.0014(11) C31 0.0318(12) 0.0618(16) 0.0361(13) -0.0074(12) -0.0046(11) 0.0152(12) C32 0.0308(12) 0.0413(13) 0.0328(12) -0.0061(10) 0.0036(10) 0.0072(10) C33 0.0311(12) 0.0418(13) 0.0326(12) -0.0108(10) 0.0022(10) 0.0035(10) C34 0.0315(12) 0.0556(15) 0.0373(13) 0.0074(11) -0.0102(10) -0.0041(11) _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 Na1 O1 2.2959(14) . ? Na1 O2 2.3291(14) 4 ? Na1 O2 2.3535(14) . ? Na1 O3 2.3785(15) . ? Na1 O4 2.5032(15) . ? Na1 C14 3.113(2) 4 ? Na1 Na2 3.1611(10) 4 ? Na1 Na1 3.3456(14) 4 ? Na2 O2 2.3057(14) . ? Na2 O1 2.3483(14) 4 ? Na2 O1 2.3523(14) . ? Na2 O5 2.3689(14) . ? Na2 O6 2.6188(15) . ? Na2 C1 3.116(2) 4 ? Na2 Na1 3.1611(10) 4 ? Na2 Na2 3.3334(14) 4 ? O1 C1 1.319(2) . ? O1 Na2 2.3483(14) 4 ? O2 C14 1.322(2) . ? O2 Na1 2.3291(14) 4 ? O3 C28 1.423(2) . ? O3 C27 1.424(2) . ? O4 C29 1.426(2) . ? O4 C30 1.431(2) . ? O5 C32 1.417(2) . ? O5 C31 1.424(2) . ? O6 C33 1.423(2) . ? O6 C34 1.432(2) . ? C1 C6 1.412(3) . ? C1 C2 1.420(3) . ? C1 Na2 3.116(2) 4 ? C2 C3 1.390(3) . ? C2 C7 1.517(3) . ? C3 C4 1.386(3) . ? C4 C5 1.375(3) . ? C5 C6 1.387(3) . ? C7 C8 1.512(3) . ? C8 C13 1.384(3) . ? C8 C9 1.389(3) . ? C9 C10 1.387(3) . ? C10 C11 1.382(3) . ? C11 C12 1.359(3) . ? C12 C13 1.393(3) . ? C14 C15 1.411(3) . ? C14 C19 1.413(3) . ? C14 Na1 3.113(2) 4 ? C15 C16 1.403(3) . ? C15 C20 1.503(3) . ? C16 C17 1.381(3) . ? C17 C18 1.375(3) . ? C18 C19 1.380(3) . ? C20 C21 1.519(3) . ? C21 C26 1.383(3) . ? C21 C22 1.379(3) . ? C22 C23 1.379(3) . ? C23 C24 1.375(3) . ? C24 C25 1.369(3) . ? C25 C26 1.384(3) . ? C28 C29 1.492(3) . ? C32 C33 1.493(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Na1 O2 93.99(5) . 4 ? O1 Na1 O2 86.95(5) . . ? O2 Na1 O2 88.77(5) 4 . ? O1 Na1 O3 130.87(5) . . ? O2 Na1 O3 133.60(5) 4 . ? O2 Na1 O3 102.88(5) . . ? O1 Na1 O4 105.91(5) . . ? O2 Na1 O4 90.92(5) 4 . ? O2 Na1 O4 167.12(5) . . ? O3 Na1 O4 68.37(5) . . ? O1 Na1 C14 114.41(5) . 4 ? O2 Na1 C14 22.80(5) 4 4 ? O2 Na1 C14 99.53(5) . 4 ? O3 Na1 C14 111.16(5) . 4 ? O4 Na1 C14 76.01(5) . 4 ? O1 Na1 Na2 47.80(4) . 4 ? O2 Na1 Na2 46.69(3) 4 4 ? O2 Na1 Na2 92.44(4) . 4 ? O3 Na1 Na2 164.63(5) . 4 ? O4 Na1 Na2 96.71(4) . 4 ? C14 Na1 Na2 66.66(4) 4 4 ? O1 Na1 Na1 89.30(4) . 4 ? O2 Na1 Na1 44.69(3) 4 4 ? O2 Na1 Na1 44.11(3) . 4 ? O3 Na1 Na1 130.75(4) . 4 ? O4 Na1 Na1 134.57(5) . 4 ? C14 Na1 Na1 58.87(4) 4 4 ? Na2 Na1 Na1 62.34(2) 4 4 ? O2 Na2 O1 93.23(5) . 4 ? O2 Na2 O1 86.75(5) . . ? O1 Na2 O1 89.65(5) 4 . ? O2 Na2 O5 129.44(5) . . ? O1 Na2 O5 136.63(5) 4 . ? O1 Na2 O5 98.99(5) . . ? O2 Na2 O6 110.76(5) . . ? O1 Na2 O6 93.36(5) 4 . ? O1 Na2 O6 161.99(5) . . ? O5 Na2 O6 66.99(5) . . ? O2 Na2 C1 112.67(5) . 4 ? O1 Na2 C1 22.88(4) 4 4 ? O1 Na2 C1 102.23(5) . 4 ? O5 Na2 C1 114.89(5) . 4 ? O6 Na2 C1 75.47(5) . 4 ? O2 Na2 Na1 47.31(3) . 4 ? O1 Na2 Na1 46.41(3) 4 4 ? O1 Na2 Na1 92.89(4) . 4 ? O5 Na2 Na1 167.58(5) . 4 ? O6 Na2 Na1 102.03(4) . 4 ? C1 Na2 Na1 65.52(4) 4 4 ? O2 Na2 Na2 89.02(4) . 4 ? O1 Na2 Na2 44.88(3) 4 4 ? O1 Na2 Na2 44.79(3) . 4 ? O5 Na2 Na2 129.31(4) . 4 ? O6 Na2 Na2 135.83(4) . 4 ? C1 Na2 Na2 60.39(4) 4 4 ? Na1 Na2 Na2 62.48(2) 4 4 ? C1 O1 Na1 138.37(12) . . ? C1 O1 Na2 113.34(11) . 4 ? Na1 O1 Na2 85.78(5) . 4 ? C1 O1 Na2 121.95(11) . . ? Na1 O1 Na2 92.97(5) . . ? Na2 O1 Na2 90.33(5) 4 . ? C14 O2 Na2 142.30(12) . . ? C14 O2 Na1 114.12(11) . 4 ? Na2 O2 Na1 86.01(5) . 4 ? C14 O2 Na1 117.02(11) . . ? Na2 O2 Na1 92.69(5) . . ? Na1 O2 Na1 91.20(5) 4 . ? C28 O3 C27 111.12(15) . . ? C28 O3 Na1 117.25(11) . . ? C27 O3 Na1 120.36(11) . . ? C29 O4 C30 110.31(15) . . ? C29 O4 Na1 110.48(11) . . ? C30 O4 Na1 122.00(12) . . ? C32 O5 C31 111.37(15) . . ? C32 O5 Na2 119.27(11) . . ? C31 O5 Na2 121.61(12) . . ? C33 O6 C34 110.43(15) . . ? C33 O6 Na2 108.35(11) . . ? C34 O6 Na2 124.28(12) . . ? O1 C1 C6 121.01(17) . . ? O1 C1 C2 121.74(17) . . ? C6 C1 C2 117.25(18) . . ? O1 C1 Na2 43.78(8) . 4 ? C6 C1 Na2 85.79(12) . 4 ? C2 C1 Na2 145.68(13) . 4 ? C3 C2 C1 119.48(18) . . ? C3 C2 C7 122.17(18) . . ? C1 C2 C7 118.35(17) . . ? C4 C3 C2 122.05(19) . . ? C5 C4 C3 118.99(19) . . ? C4 C5 C6 120.57(19) . . ? C5 C6 C1 121.54(19) . . ? C8 C7 C2 115.09(16) . . ? C13 C8 C9 117.2(2) . . ? C13 C8 C7 122.3(2) . . ? C9 C8 C7 120.5(2) . . ? C10 C9 C8 121.4(2) . . ? C9 C10 C11 120.2(2) . . ? C12 C11 C10 119.2(2) . . ? C11 C12 C13 120.7(2) . . ? C8 C13 C12 121.2(2) . . ? O2 C14 C15 121.09(17) . . ? O2 C14 C19 121.69(18) . . ? C15 C14 C19 117.21(18) . . ? O2 C14 Na1 43.07(8) . 4 ? C15 C14 Na1 149.20(14) . 4 ? C19 C14 Na1 84.76(12) . 4 ? C16 C15 C14 119.34(18) . . ? C16 C15 C20 123.28(18) . . ? C14 C15 C20 117.38(17) . . ? C17 C16 C15 121.96(19) . . ? C18 C17 C16 118.9(2) . . ? C17 C18 C19 120.6(2) . . ? C18 C19 C14 121.9(2) . . ? C15 C20 C21 116.18(17) . . ? C26 C21 C22 117.8(2) . . ? C26 C21 C20 121.3(2) . . ? C22 C21 C20 121.0(2) . . ? C23 C22 C21 121.2(2) . . ? C24 C23 C22 120.3(2) . . ? C25 C24 C23 119.5(2) . . ? C24 C25 C26 120.1(2) . . ? C21 C26 C25 121.2(2) . . ? O3 C28 C29 108.77(16) . . ? O4 C29 C28 109.56(15) . . ? O5 C32 C33 109.13(16) . . ? O6 C33 C32 109.18(16) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.229 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.048 _chemical_compound_source DME #===END data_COMPPOUND_HOdbpOMe _database_code_depnum_ccdc_archive 'CCDC 299160' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 396 _chemical_formula_moiety 'C22 H22 O3' _chemical_formula_sum 'C22 H22 O3' _chemical_formula_weight 334.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.7898(2) _cell_length_b 10.4137(3) _cell_length_c 24.7155(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1747.56(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13157 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 28.09 _reflns_number_total 4184 _reflns_number_gt 3257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0420P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(9) _refine_ls_number_reflns 4184 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.08699(15) 0.54638(10) 0.88363(4) 0.0224(2) Uani 1 1 d . . . O2 O 0.29747(16) 0.74175(10) 0.83735(4) 0.0285(3) Uani 1 1 d . . . O3 O -0.50302(16) 0.29114(10) 0.83830(4) 0.0289(3) Uani 1 1 d . . . C1 C -0.0932(2) 0.58259(13) 0.90362(6) 0.0179(3) Uani 1 1 d . . . C2 C -0.1372(2) 0.70965(13) 0.91774(5) 0.0191(3) Uani 1 1 d . . . C3 C -0.3235(2) 0.73530(14) 0.93938(6) 0.0210(3) Uani 1 1 d . . . C4 C -0.4610(2) 0.63826(14) 0.94640(6) 0.0214(3) Uani 1 1 d . . . C5 C -0.4140(2) 0.51294(14) 0.93218(6) 0.0199(3) Uani 1 1 d . . . C6 C -0.2291(2) 0.48313(12) 0.91077(6) 0.0173(3) Uani 1 1 d . . . C7 C 0.0115(2) 0.81809(14) 0.91175(6) 0.0206(3) Uani 1 1 d . . . C8 C 0.0271(2) 0.87551(13) 0.85552(6) 0.0207(3) Uani 1 1 d . . . C9 C 0.1753(2) 0.83850(14) 0.81920(6) 0.0235(3) Uani 1 1 d . . . C10 C 0.1942(3) 0.89622(15) 0.76880(7) 0.0292(4) Uani 1 1 d . . . C11 C 0.0639(3) 0.99295(17) 0.75426(7) 0.0347(4) Uani 1 1 d . . . C12 C -0.0831(3) 1.03141(16) 0.78922(7) 0.0327(4) Uani 1 1 d . . . C13 C -0.1015(3) 0.97256(14) 0.83947(7) 0.0268(4) Uani 1 1 d . . . C14 C 0.4751(2) 0.71526(19) 0.80813(7) 0.0299(4) Uani 1 1 d . . . C15 C -0.1672(2) 0.34706(13) 0.89628(6) 0.0200(3) Uani 1 1 d . . . C16 C -0.3085(2) 0.24397(12) 0.91402(6) 0.0205(3) Uani 1 1 d . . . C17 C -0.4808(2) 0.21912(13) 0.88457(6) 0.0226(3) Uani 1 1 d . . . C18 C -0.6141(2) 0.12661(15) 0.90199(7) 0.0296(4) Uani 1 1 d . . . C19 C -0.5758(3) 0.05819(15) 0.94893(7) 0.0314(4) Uani 1 1 d . . . C20 C -0.4057(3) 0.08021(14) 0.97846(7) 0.0286(4) Uani 1 1 d . . . C21 C -0.2739(2) 0.17295(13) 0.96085(6) 0.0236(3) Uani 1 1 d . . . C22 C -0.6954(3) 0.2969(2) 0.81527(8) 0.0378(4) Uani 1 1 d . . . H1 H 0.153(3) 0.613(2) 0.8747(8) 0.050(6) Uiso 1 1 d . . . H3 H -0.357(2) 0.8278(15) 0.9494(6) 0.022(4) Uiso 1 1 d . . . H4 H -0.592(2) 0.6592(13) 0.9611(6) 0.021(4) Uiso 1 1 d . . . H5 H -0.514(2) 0.4431(15) 0.9377(6) 0.025(4) Uiso 1 1 d . . . H7A H 0.150(3) 0.7878(14) 0.9228(6) 0.022(4) Uiso 1 1 d . . . H7B H -0.033(2) 0.8850(14) 0.9367(6) 0.020(4) Uiso 1 1 d . . . H10 H 0.303(3) 0.8721(16) 0.7454(7) 0.034(5) Uiso 1 1 d . . . H11 H 0.077(3) 1.0354(17) 0.7198(8) 0.042(5) Uiso 1 1 d . . . H12 H -0.174(3) 1.1036(16) 0.7800(7) 0.034(5) Uiso 1 1 d . . . H13 H -0.206(3) 1.0011(15) 0.8662(7) 0.030(4) Uiso 1 1 d . . . H14A H 0.545(3) 0.6420(18) 0.8280(7) 0.043(5) Uiso 1 1 d . . . H14B H 0.563(3) 0.7950(19) 0.8072(8) 0.047(5) Uiso 1 1 d . . . H14C H 0.449(3) 0.6829(16) 0.7709(8) 0.039(5) Uiso 1 1 d . . . H15A H -0.037(2) 0.3322(14) 0.9129(6) 0.024(4) Uiso 1 1 d . . . H15B H -0.143(2) 0.3412(15) 0.8575(7) 0.027(4) Uiso 1 1 d . . . H18 H -0.731(2) 0.1111(14) 0.8809(6) 0.025(4) Uiso 1 1 d . . . H19 H -0.671(3) -0.0075(17) 0.9618(7) 0.042(5) Uiso 1 1 d . . . H20 H -0.381(2) 0.0304(15) 1.0117(7) 0.029(4) Uiso 1 1 d . . . H21 H -0.149(2) 0.1940(14) 0.9813(6) 0.024(4) Uiso 1 1 d . . . H22A H -0.689(3) 0.3586(19) 0.7832(8) 0.046(5) Uiso 1 1 d . . . H22B H -0.795(3) 0.3283(17) 0.8430(7) 0.041(5) Uiso 1 1 d . . . H22C H -0.735(3) 0.2099(18) 0.8031(7) 0.036(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0175(5) 0.0208(5) 0.0290(6) -0.0012(5) 0.0057(5) -0.0018(4) O2 0.0240(6) 0.0301(6) 0.0314(6) 0.0093(5) 0.0079(5) 0.0033(5) O3 0.0208(6) 0.0367(6) 0.0292(6) 0.0010(5) -0.0029(5) -0.0020(5) C1 0.0169(7) 0.0215(7) 0.0154(7) 0.0015(6) -0.0001(6) 0.0022(6) C2 0.0224(8) 0.0195(7) 0.0155(7) -0.0003(6) -0.0018(6) -0.0018(6) C3 0.0243(8) 0.0194(7) 0.0191(7) -0.0026(6) -0.0014(7) 0.0034(6) C4 0.0187(8) 0.0259(8) 0.0195(8) -0.0007(7) 0.0015(7) 0.0064(6) C5 0.0191(7) 0.0225(7) 0.0181(7) 0.0038(6) 0.0016(6) -0.0009(7) C6 0.0180(7) 0.0175(6) 0.0164(7) 0.0011(6) -0.0028(6) 0.0003(6) C7 0.0214(8) 0.0188(7) 0.0215(8) -0.0029(7) -0.0005(7) -0.0019(6) C8 0.0237(8) 0.0172(7) 0.0213(8) -0.0009(6) -0.0048(7) -0.0052(6) C9 0.0262(8) 0.0202(7) 0.0240(8) 0.0022(6) -0.0038(7) -0.0055(7) C10 0.0337(10) 0.0288(8) 0.0250(8) 0.0011(7) -0.0004(8) -0.0070(8) C11 0.0437(11) 0.0338(9) 0.0266(9) 0.0083(8) -0.0114(8) -0.0076(9) C12 0.0365(10) 0.0239(8) 0.0378(10) 0.0049(8) -0.0130(9) -0.0011(8) C13 0.0287(8) 0.0189(7) 0.0329(9) -0.0004(7) -0.0048(8) -0.0017(7) C14 0.0213(9) 0.0426(10) 0.0258(9) -0.0011(9) 0.0040(7) -0.0015(9) C15 0.0177(8) 0.0207(7) 0.0216(8) -0.0001(6) 0.0017(7) -0.0004(6) C16 0.0210(8) 0.0161(7) 0.0244(8) -0.0042(6) 0.0051(7) 0.0000(6) C17 0.0219(8) 0.0207(7) 0.0252(8) -0.0045(7) 0.0028(7) 0.0022(7) C18 0.0235(8) 0.0248(8) 0.0404(10) -0.0101(8) 0.0051(8) -0.0057(7) C19 0.0338(10) 0.0175(7) 0.0430(10) -0.0044(8) 0.0148(9) -0.0065(7) C20 0.0381(10) 0.0171(7) 0.0306(9) -0.0004(7) 0.0114(8) 0.0008(7) C21 0.0274(9) 0.0169(7) 0.0264(8) -0.0036(7) 0.0051(7) 0.0025(7) C22 0.0224(9) 0.0598(13) 0.0313(9) -0.0047(10) -0.0011(8) 0.0064(9) _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 1.3724(17) . ? O2 C9 1.3798(18) . ? O2 C14 1.433(2) . ? O3 C17 1.3759(17) . ? O3 C22 1.426(2) . ? C1 C6 1.3983(19) . ? C1 C2 1.401(2) . ? C2 C3 1.399(2) . ? C2 C7 1.522(2) . ? C3 C4 1.387(2) . ? C4 C5 1.389(2) . ? C5 C6 1.397(2) . ? C6 C15 1.5207(19) . ? C7 C8 1.517(2) . ? C8 C13 1.393(2) . ? C8 C9 1.403(2) . ? C9 C10 1.389(2) . ? C10 C11 1.388(2) . ? C11 C12 1.380(3) . ? C12 C13 1.390(2) . ? C15 C16 1.505(2) . ? C16 C21 1.393(2) . ? C16 C17 1.402(2) . ? C17 C18 1.390(2) . ? C18 C19 1.386(3) . ? C19 C20 1.385(2) . ? C20 C21 1.387(2) . ? 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 C9 O2 C14 118.86(12) . . ? C17 O3 C22 117.08(13) . . ? O1 C1 C6 115.48(12) . . ? O1 C1 C2 122.63(13) . . ? C6 C1 C2 121.85(12) . . ? C3 C2 C1 117.92(13) . . ? C3 C2 C7 119.68(13) . . ? C1 C2 C7 122.39(13) . . ? C4 C3 C2 121.16(14) . . ? C3 C4 C5 119.90(14) . . ? C4 C5 C6 120.73(14) . . ? C5 C6 C1 118.43(12) . . ? C5 C6 C15 122.98(12) . . ? C1 C6 C15 118.56(12) . . ? C8 C7 C2 115.35(12) . . ? C13 C8 C9 117.82(14) . . ? C13 C8 C7 120.21(14) . . ? C9 C8 C7 121.89(13) . . ? O2 C9 C10 123.51(15) . . ? O2 C9 C8 115.08(13) . . ? C10 C9 C8 121.42(15) . . ? C11 C10 C9 119.17(17) . . ? C12 C11 C10 120.65(16) . . ? C11 C12 C13 119.75(16) . . ? C12 C13 C8 121.19(16) . . ? C16 C15 C6 114.83(12) . . ? C21 C16 C17 118.29(13) . . ? C21 C16 C15 120.89(14) . . ? C17 C16 C15 120.81(13) . . ? O3 C17 C18 124.31(14) . . ? O3 C17 C16 115.00(12) . . ? C18 C17 C16 120.68(15) . . ? C19 C18 C17 119.56(16) . . ? C20 C19 C18 120.82(15) . . ? C19 C20 C21 119.18(16) . . ? C20 C21 C16 121.46(16) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.09 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.191 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.044 _chemical_compound_source acetone #===END