Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dilip Dhavale' _publ_contact_author_address ; Department of Chemistry University of Pune Pune India 411 007 INDIA ; _publ_contact_author_email DDD@CHEM.UNIPUNE.ERNET.IN _publ_section_title ; Synthesis and Glycosidase Inhibitory Studies of Tetrahydroxy Perhydroaza-azulenes: Tandem Johnson-Claisen Rearrangement of D-Glucose Derived Allylic Alcohols ; loop_ _publ_author_name 'Dilip Dhavale' 'N. S. Karanjule' 'Shankkar D. Markad' 'Vedavati G. Puranik' 'Sushma G. Sabharwal' ; T.Sharma ; data_C20H25NO6 _database_code_depnum_ccdc_archive 'CCDC 600972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Derived Allylic Alcohols' _chemical_melting_point ? _chemical_formula_moiety 'C20 H25 N O6' _chemical_formula_sum 'C20 H25 N O6' _chemical_formula_weight 375.41 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' N N 0.0061 0.0033 '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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.5259(4) _cell_length_b 10.0212(7) _cell_length_c 34.600(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1916.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3458 _cell_measurement_theta_min 2.388 _cell_measurement_theta_max 24.875 _exptl_crystal_description colourless _exptl_crystal_colour needle _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9499 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ' CCD Area Detector' _diffrn_measurement_device ' Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9697 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3372 _reflns_number_gt 3021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL and PLATON' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.5758P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(19) _refine_ls_number_reflns 3372 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1473 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.1724(4) 0.6034(2) 0.84127(6) 0.0673(7) Uani 1 1 d . . . O2 O 1.1780(5) 0.3741(2) 0.84841(7) 0.0738(7) Uani 1 1 d . . . O3 O 0.8849(4) 0.4052(2) 0.89298(6) 0.0620(6) Uani 1 1 d . . . O4 O 1.0877(5) 0.7406(2) 0.91460(6) 0.0683(7) Uani 1 1 d . . . O5 O 0.7154(5) 0.8611(2) 0.85110(7) 0.0708(7) Uani 1 1 d . . . O6 O 0.4213(5) 0.9856(3) 0.82512(9) 0.0852(8) Uani 1 1 d . . . N N 0.7499(6) 0.9200(3) 0.78920(8) 0.0629(7) Uani 1 1 d . . . C1 C 1.2291(6) 0.4959(4) 0.86557(9) 0.0596(8) Uani 1 1 d . . . H1 H 1.3987 0.5000 0.8738 0.072 Uiso 1 1 calc R . . C2 C 1.0591(6) 0.5058(4) 0.90039(9) 0.0598(8) Uani 1 1 d . . . H2 H 1.1429 0.4933 0.9251 0.072 Uiso 1 1 calc R . . C3 C 0.9432(6) 0.6426(3) 0.89668(9) 0.0553(8) Uani 1 1 d . . . H3 H 0.7779 0.6430 0.9069 0.066 Uiso 1 1 calc R . . C4 C 0.9453(6) 0.6593(3) 0.85304(9) 0.0582(8) Uani 1 1 d . . . H4 H 0.8124 0.6079 0.8416 0.070 Uiso 1 1 calc R . . C5 C 0.9382(6) 0.8001(3) 0.83814(10) 0.0610(9) Uani 1 1 d . . . H5 H 1.0771 0.8503 0.8481 0.073 Uiso 1 1 calc R . . C6 C 0.9265(8) 0.8128(4) 0.79396(10) 0.0708(10) Uani 1 1 d . . . H6 H 1.0841 0.8418 0.7840 0.085 Uiso 1 1 calc R . . C7 C 0.8298(11) 0.7003(4) 0.76918(12) 0.1062(18) Uani 1 1 d . . . H7A H 0.9597 0.6602 0.7543 0.127 Uiso 1 1 calc R . . H7B H 0.7569 0.6320 0.7852 0.127 Uiso 1 1 calc R . . C8 C 0.6461(10) 0.7595(4) 0.74300(14) 0.0992(14) Uani 1 1 d . . . H8A H 0.6923 0.7455 0.7163 0.119 Uiso 1 1 calc R . . H8B H 0.4898 0.7179 0.7472 0.119 Uiso 1 1 calc R . . C9 C 0.6326(8) 0.9039(4) 0.75157(10) 0.0762(10) Uani 1 1 d . . . H9A H 0.7166 0.9551 0.7319 0.091 Uiso 1 1 calc R . . H9B H 0.4655 0.9333 0.7527 0.091 Uiso 1 1 calc R . . C10 C 0.6098(7) 0.9285(3) 0.82117(11) 0.0637(9) Uani 1 1 d . . . C11 C 0.9919(7) 0.3068(3) 0.86874(11) 0.0648(9) Uani 1 1 d . . . C12 C 1.1032(13) 0.1979(5) 0.89224(16) 0.135(2) Uani 1 1 d . . . H12A H 1.1977 0.2362 0.9127 0.202 Uiso 1 1 calc R . . H12B H 1.2055 0.1443 0.8760 0.202 Uiso 1 1 calc R . . H12C H 0.9778 0.1431 0.9031 0.202 Uiso 1 1 calc R . . C13 C 0.8036(9) 0.2610(5) 0.84088(16) 0.1191(19) Uani 1 1 d . . . H13A H 0.6755 0.2173 0.8547 0.179 Uiso 1 1 calc R . . H13B H 0.8745 0.1997 0.8228 0.179 Uiso 1 1 calc R . . H13C H 0.7396 0.3365 0.8272 0.179 Uiso 1 1 calc R . . C14 C 1.0084(7) 0.7792(4) 0.95049(11) 0.0743(11) Uani 1 1 d . . . H14A H 1.0181 0.7039 0.9681 0.089 Uiso 1 1 calc R . . H14B H 0.8403 0.8064 0.9488 0.089 Uiso 1 1 calc R . . C15 C 1.1563(6) 0.8922(3) 0.96616(9) 0.0581(8) Uani 1 1 d . . . C16 C 1.3603(7) 0.9389(4) 0.94779(11) 0.0697(10) Uani 1 1 d . . . H16 H 1.4111 0.9015 0.9246 0.084 Uiso 1 1 calc R . . C17 C 1.4892(9) 1.0434(4) 0.96469(15) 0.0923(14) Uani 1 1 d . . . H17 H 1.6294 1.0745 0.9528 0.111 Uiso 1 1 calc R . . C18 C 1.4122(11) 1.1012(4) 0.99868(14) 0.0911(15) Uani 1 1 d . . . H18 H 1.4979 1.1719 1.0095 0.109 Uiso 1 1 calc R . . C19 C 1.2141(10) 1.0549(4) 1.01589(13) 0.0872(14) Uani 1 1 d . . . H19 H 1.1629 1.0930 1.0390 0.105 Uiso 1 1 calc R . . C20 C 1.0840(8) 0.9517(4) 1.00015(11) 0.0735(11) Uani 1 1 d . . . H20 H 0.9452 0.9216 1.0126 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0753(16) 0.0725(15) 0.0542(12) -0.0021(12) 0.0145(11) 0.0004(13) O2 0.0778(16) 0.0712(15) 0.0724(15) -0.0203(13) 0.0204(13) -0.0080(14) O3 0.0665(14) 0.0577(13) 0.0619(13) -0.0116(11) 0.0125(11) -0.0064(12) O4 0.0747(16) 0.0782(16) 0.0521(12) -0.0241(11) 0.0080(12) -0.0268(14) O5 0.0831(17) 0.0682(14) 0.0611(14) -0.0087(12) 0.0123(13) 0.0030(14) O6 0.0814(19) 0.0610(15) 0.113(2) -0.0097(15) 0.0148(17) 0.0085(16) N 0.0700(18) 0.0554(16) 0.0633(16) 0.0032(13) 0.0054(15) -0.0110(15) C1 0.0510(18) 0.071(2) 0.0567(18) -0.0078(17) -0.0043(16) -0.0037(18) C2 0.070(2) 0.070(2) 0.0402(16) -0.0097(15) -0.0081(15) -0.0102(19) C3 0.0573(18) 0.0600(18) 0.0486(16) -0.0159(15) 0.0020(15) -0.0084(17) C4 0.063(2) 0.065(2) 0.0465(17) -0.0102(15) 0.0010(15) -0.0118(17) C5 0.0604(19) 0.066(2) 0.0568(19) -0.0089(15) 0.0010(16) -0.0146(18) C6 0.074(2) 0.084(3) 0.055(2) 0.0007(18) 0.0045(18) 0.000(2) C7 0.175(5) 0.083(3) 0.061(2) -0.019(2) -0.031(3) 0.035(3) C8 0.122(4) 0.085(3) 0.091(3) -0.016(2) -0.019(3) 0.008(3) C9 0.086(3) 0.077(2) 0.065(2) 0.0151(19) -0.006(2) 0.000(2) C10 0.076(3) 0.0384(16) 0.076(2) -0.0069(16) 0.006(2) -0.0121(19) C11 0.073(2) 0.0544(19) 0.067(2) -0.0105(16) 0.0178(18) -0.0041(18) C12 0.197(6) 0.096(3) 0.112(4) 0.030(3) 0.052(4) 0.062(4) C13 0.091(3) 0.120(4) 0.146(4) -0.081(4) 0.003(3) -0.022(3) C14 0.071(2) 0.083(2) 0.069(2) -0.031(2) 0.0027(19) -0.009(2) C15 0.063(2) 0.0526(18) 0.0591(18) -0.0105(15) -0.0157(16) 0.0055(17) C16 0.070(2) 0.067(2) 0.072(2) -0.0045(18) -0.015(2) -0.005(2) C17 0.091(3) 0.081(3) 0.105(3) 0.013(3) -0.024(3) -0.026(3) C18 0.123(4) 0.054(2) 0.096(3) -0.007(2) -0.055(3) -0.013(3) C19 0.121(4) 0.064(3) 0.076(3) -0.020(2) -0.043(3) 0.015(3) C20 0.076(2) 0.075(2) 0.070(2) -0.0188(18) -0.013(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.402(4) . ? O1 C4 1.433(4) . ? O2 C1 1.386(4) . ? O2 C11 1.416(4) . ? O3 C2 1.417(4) . ? O3 C11 1.423(4) . ? O4 C14 1.372(4) . ? O4 C3 1.410(4) . ? O5 C10 1.367(4) . ? O5 C5 1.446(4) . ? O6 C10 1.196(5) . ? N C10 1.353(5) . ? N C6 1.461(5) . ? N C9 1.463(4) . ? C1 C2 1.531(5) . ? C1 H1 0.9800 . ? C2 C3 1.519(5) . ? C2 H2 0.9800 . ? C3 C4 1.519(4) . ? C3 H3 0.9800 . ? C4 C5 1.503(5) . ? C4 H4 0.9800 . ? C5 C6 1.535(5) . ? C5 H5 0.9800 . ? C6 C7 1.514(6) . ? C6 H6 0.9800 . ? C7 C8 1.484(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.480(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.494(6) . ? C11 C13 1.491(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.498(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.376(5) . ? C15 C20 1.378(5) . ? C16 C17 1.395(5) . ? C16 H16 0.9300 . ? C17 C18 1.378(7) . ? C17 H17 0.9300 . ? C18 C19 1.330(7) . ? C18 H18 0.9300 . ? C19 C20 1.371(6) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 C4 109.0(2) . . ? C1 O2 C11 110.8(3) . . ? C2 O3 C11 108.5(2) . . ? C14 O4 C3 114.4(3) . . ? C10 O5 C5 109.7(3) . . ? C10 N C6 109.6(3) . . ? C10 N C9 118.7(3) . . ? C6 N C9 108.4(3) . . ? O2 C1 O1 112.0(2) . . ? O2 C1 C2 105.6(3) . . ? O1 C1 C2 106.6(3) . . ? O2 C1 H1 110.8 . . ? O1 C1 H1 110.8 . . ? C2 C1 H1 110.8 . . ? O3 C2 C3 109.9(3) . . ? O3 C2 C1 103.2(2) . . ? C3 C2 C1 104.5(3) . . ? O3 C2 H2 112.8 . . ? C3 C2 H2 112.8 . . ? C1 C2 H2 112.8 . . ? O4 C3 C2 110.7(3) . . ? O4 C3 C4 110.8(3) . . ? C2 C3 C4 100.4(2) . . ? O4 C3 H3 111.5 . . ? C2 C3 H3 111.5 . . ? C4 C3 H3 111.5 . . ? O1 C4 C5 107.0(3) . . ? O1 C4 C3 104.2(3) . . ? C5 C4 C3 116.4(3) . . ? O1 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? O5 C5 C4 108.2(3) . . ? O5 C5 C6 103.8(3) . . ? C4 C5 C6 114.9(3) . . ? O5 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? N C6 C7 104.3(3) . . ? N C6 C5 101.6(3) . . ? C7 C6 C5 121.1(3) . . ? N C6 H6 109.6 . . ? C7 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C8 C7 C6 106.8(4) . . ? C8 C7 H7A 110.4 . . ? C6 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? C6 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 107.6(4) . . ? C9 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? C9 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N C9 C8 105.3(3) . . ? N C9 H9A 110.7 . . ? C8 C9 H9A 110.7 . . ? N C9 H9B 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? O6 C10 N 128.4(4) . . ? O6 C10 O5 121.4(3) . . ? N C10 O5 110.1(3) . . ? O2 C11 O3 105.3(3) . . ? O2 C11 C12 108.6(4) . . ? O3 C11 C12 110.9(3) . . ? O2 C11 C13 109.4(3) . . ? O3 C11 C13 107.7(3) . . ? C12 C11 C13 114.5(4) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 C15 111.5(3) . . ? O4 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? O4 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C20 119.0(3) . . ? C16 C15 C14 122.5(3) . . ? C20 C15 C14 118.6(3) . . ? C15 C16 C17 118.7(4) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C18 C17 C16 121.0(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.3(4) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 121.1(4) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C20 C15 120.9(4) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 O2 C1 O1 -115.1(3) . . . . ? C11 O2 C1 C2 0.4(4) . . . . ? C4 O1 C1 O2 100.9(3) . . . . ? C4 O1 C1 C2 -14.1(3) . . . . ? C11 O3 C2 C3 136.1(3) . . . . ? C11 O3 C2 C1 25.1(3) . . . . ? O2 C1 C2 O3 -15.5(3) . . . . ? O1 C1 C2 O3 103.7(3) . . . . ? O2 C1 C2 C3 -130.5(3) . . . . ? O1 C1 C2 C3 -11.3(3) . . . . ? C14 O4 C3 C2 -101.3(4) . . . . ? C14 O4 C3 C4 148.3(3) . . . . ? O3 C2 C3 O4 162.7(2) . . . . ? C1 C2 C3 O4 -87.1(3) . . . . ? O3 C2 C3 C4 -80.2(3) . . . . ? C1 C2 C3 C4 30.0(3) . . . . ? C1 O1 C4 C5 157.9(2) . . . . ? C1 O1 C4 C3 34.1(3) . . . . ? O4 C3 C4 O1 78.1(3) . . . . ? C2 C3 C4 O1 -38.8(3) . . . . ? O4 C3 C4 C5 -39.4(4) . . . . ? C2 C3 C4 C5 -156.4(3) . . . . ? C10 O5 C5 C4 -134.7(3) . . . . ? C10 O5 C5 C6 -12.2(3) . . . . ? O1 C4 C5 O5 -177.4(2) . . . . ? C3 C4 C5 O5 -61.4(4) . . . . ? O1 C4 C5 C6 67.2(4) . . . . ? C3 C4 C5 C6 -176.8(3) . . . . ? C10 N C6 C7 104.2(4) . . . . ? C9 N C6 C7 -26.8(4) . . . . ? C10 N C6 C5 -22.4(4) . . . . ? C9 N C6 C5 -153.5(3) . . . . ? O5 C5 C6 N 20.2(3) . . . . ? C4 C5 C6 N 138.1(3) . . . . ? O5 C5 C6 C7 -94.6(4) . . . . ? C4 C5 C6 C7 23.3(6) . . . . ? N C6 C7 C8 16.0(5) . . . . ? C5 C6 C7 C8 129.4(4) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C10 N C9 C8 -98.6(4) . . . . ? C6 N C9 C8 27.3(4) . . . . ? C7 C8 C9 N -16.4(5) . . . . ? C6 N C10 O6 -164.8(3) . . . . ? C9 N C10 O6 -39.5(5) . . . . ? C6 N C10 O5 16.1(4) . . . . ? C9 N C10 O5 141.4(3) . . . . ? C5 O5 C10 O6 179.1(3) . . . . ? C5 O5 C10 N -1.7(4) . . . . ? C1 O2 C11 O3 14.9(4) . . . . ? C1 O2 C11 C12 -103.9(4) . . . . ? C1 O2 C11 C13 130.5(3) . . . . ? C2 O3 C11 O2 -25.5(4) . . . . ? C2 O3 C11 C12 91.9(4) . . . . ? C2 O3 C11 C13 -142.2(3) . . . . ? C3 O4 C14 C15 -174.6(3) . . . . ? O4 C14 C15 C16 -6.4(5) . . . . ? O4 C14 C15 C20 173.3(3) . . . . ? C20 C15 C16 C17 1.2(5) . . . . ? C14 C15 C16 C17 -179.1(4) . . . . ? C15 C16 C17 C18 -1.4(6) . . . . ? C16 C17 C18 C19 1.2(7) . . . . ? C17 C18 C19 C20 -0.8(6) . . . . ? C18 C19 C20 C15 0.6(6) . . . . ? C16 C15 C20 C19 -0.8(5) . . . . ? C14 C15 C20 C19 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.038