Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_saka3_p212121 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O4' _chemical_formula_weight 395.45 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 P2(1)2(1)2(1) 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 11.32160(10) _cell_length_b 13.26990(10) _cell_length_c 13.7391(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2064.11(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 4644 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 26.59 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 15461 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 32.75 _reflns_number_total 7300 _reflns_number_gt 5281 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.0219P] 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(10) _refine_ls_number_reflns 7300 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 C1 C 0.38485(14) -0.03928(10) 0.06698(12) 0.0524(4) Uani 1 1 d . . . C2 C 0.50944(14) -0.07610(10) 0.05079(10) 0.0463(3) Uani 1 1 d . . . C3 C 0.60525(11) -0.05414(8) 0.13077(9) 0.0347(2) Uani 1 1 d . . . C4 C 0.55044(11) -0.02435(9) 0.22745(8) 0.0340(2) Uani 1 1 d . . . C5 C 0.62469(12) -0.00848(11) 0.30680(9) 0.0429(3) Uani 1 1 d . . . H5 H 0.7058 -0.0164 0.2991 0.052 Uiso 1 1 calc R . . C6 C 0.58034(16) 0.01885(12) 0.39669(10) 0.0550(4) Uani 1 1 d . . . H6 H 0.6309 0.0286 0.4492 0.066 Uiso 1 1 calc R . . C7 C 0.46042(17) 0.03150(11) 0.40753(11) 0.0587(4) Uani 1 1 d . . . H7 H 0.4299 0.0495 0.4679 0.070 Uiso 1 1 calc R . . C8 C 0.38554(14) 0.01792(11) 0.33049(12) 0.0537(4) Uani 1 1 d . . . H8 H 0.3048 0.0272 0.3391 0.064 Uiso 1 1 calc R . . C9 C 0.42875(11) -0.00961(9) 0.23916(10) 0.0403(3) Uani 1 1 d . . . C10 C 0.22371(14) 0.00234(18) 0.17530(18) 0.0820(6) Uani 1 1 d . . . H10A H 0.1819 -0.0049 0.1149 0.123 Uiso 1 1 calc R . . H10B H 0.2142 0.0698 0.1992 0.123 Uiso 1 1 calc R . . H10C H 0.1927 -0.0445 0.2220 0.123 Uiso 1 1 calc R . . C11 C 0.5477(2) -0.05504(14) -0.05416(11) 0.0690(5) Uani 1 1 d . . . H11A H 0.4922 -0.0851 -0.0983 0.103 Uiso 1 1 calc R . . H11B H 0.6247 -0.0833 -0.0651 0.103 Uiso 1 1 calc R . . H11C H 0.5504 0.0164 -0.0649 0.103 Uiso 1 1 calc R . . C12 C 0.70763(11) 0.01892(10) 0.11190(9) 0.0383(2) Uani 1 1 d . . . C13 C 0.77770(14) 0.18656(11) 0.07406(11) 0.0509(3) Uani 1 1 d . . . H13 H 0.8353 0.1624 0.0262 0.061 Uiso 1 1 calc R . . C14 C 0.71363(17) 0.28059(12) 0.03564(13) 0.0620(4) Uani 1 1 d . . . H14A H 0.7536 0.3417 0.0562 0.074 Uiso 1 1 calc R . . H14B H 0.7089 0.2797 -0.0348 0.074 Uiso 1 1 calc R . . C15 C 0.59203(16) 0.27321(12) 0.08081(15) 0.0640(4) Uani 1 1 d . . . H15A H 0.5924 0.2996 0.1467 0.077 Uiso 1 1 calc R . . H15B H 0.5346 0.3103 0.0426 0.077 Uiso 1 1 calc R . . C16 C 0.56434(14) 0.16242(11) 0.08059(13) 0.0543(4) Uani 1 1 d . . . H16A H 0.5165 0.1442 0.1365 0.065 Uiso 1 1 calc R . . H16B H 0.5228 0.1433 0.0217 0.065 Uiso 1 1 calc R . . C17 C 0.83742(15) 0.20889(13) 0.16960(13) 0.0565(4) Uani 1 1 d . . . C18 C 1.0125(2) 0.2770(2) 0.2361(2) 0.1052(9) Uani 1 1 d . . . H18A H 0.9608 0.3091 0.2820 0.158 Uiso 1 1 calc R . . H18B H 1.0724 0.3237 0.2160 0.158 Uiso 1 1 calc R . . H18C H 1.0489 0.2195 0.2661 0.158 Uiso 1 1 calc R . . C19 C 0.51703(15) -0.19010(10) 0.07949(12) 0.0524(4) Uani 1 1 d . . . H19A H 0.4563 -0.2111 0.1249 0.063 Uiso 1 1 calc R . . H19B H 0.5206 -0.2352 0.0240 0.063 Uiso 1 1 calc R . . C20 C 0.63897(12) -0.17095(9) 0.12802(10) 0.0421(3) Uani 1 1 d . . . C21 C 0.65377(12) -0.21739(10) 0.22413(11) 0.0454(3) Uani 1 1 d . . . C22 C 0.74308(17) -0.20640(12) 0.06463(12) 0.0608(4) Uani 1 1 d . . . H22A H 0.8160 -0.1840 0.0930 0.091 Uiso 1 1 calc R . . H22B H 0.7353 -0.1787 0.0004 0.091 Uiso 1 1 calc R . . H22C H 0.7429 -0.2786 0.0609 0.091 Uiso 1 1 calc R . . N1 N 0.34980(10) -0.01826(9) 0.15956(11) 0.0522(3) Uani 1 1 d . . . N2 N 0.68167(10) 0.11374(8) 0.08531(9) 0.0440(3) Uani 1 1 d . . . N3 N 0.66844(13) -0.25540(11) 0.29738(12) 0.0628(4) Uani 1 1 d . . . O1 O 0.31531(13) -0.03636(11) -0.00085(11) 0.0801(4) Uani 1 1 d . . . O2 O 0.81024(9) -0.00801(8) 0.12576(8) 0.0524(3) Uani 1 1 d . . . O3 O 0.79430(13) 0.20218(14) 0.24810(10) 0.0834(4) Uani 1 1 d . . . O4 O 0.94579(12) 0.24506(12) 0.15299(11) 0.0836(4) 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 C1 0.0539(8) 0.0354(6) 0.0680(10) -0.0021(6) -0.0263(7) 0.0007(5) C2 0.0616(8) 0.0358(6) 0.0416(7) -0.0057(5) -0.0139(6) 0.0021(6) C3 0.0382(6) 0.0311(5) 0.0348(5) -0.0016(4) -0.0004(5) 0.0026(4) C4 0.0357(5) 0.0316(5) 0.0348(5) -0.0001(4) 0.0005(4) -0.0015(4) C5 0.0445(6) 0.0446(7) 0.0397(6) -0.0019(5) -0.0038(5) -0.0053(5) C6 0.0793(11) 0.0502(8) 0.0356(7) -0.0019(6) -0.0027(7) -0.0096(7) C7 0.0852(12) 0.0464(8) 0.0445(8) -0.0004(6) 0.0250(8) 0.0020(7) C8 0.0531(8) 0.0422(7) 0.0659(9) 0.0058(6) 0.0229(7) 0.0036(6) C9 0.0385(6) 0.0307(5) 0.0517(7) 0.0019(5) 0.0035(5) -0.0011(4) C10 0.0352(8) 0.0843(13) 0.1264(18) -0.0031(13) -0.0085(9) 0.0004(8) C11 0.1075(15) 0.0604(9) 0.0390(8) -0.0063(6) -0.0129(9) 0.0074(10) C12 0.0415(6) 0.0381(6) 0.0352(6) -0.0029(4) 0.0074(5) 0.0015(5) C13 0.0530(8) 0.0446(7) 0.0553(8) 0.0011(6) 0.0174(7) -0.0080(6) C14 0.0802(11) 0.0446(8) 0.0611(9) 0.0119(7) 0.0055(9) -0.0092(7) C15 0.0658(10) 0.0396(7) 0.0865(12) 0.0066(7) -0.0074(9) 0.0021(6) C16 0.0511(8) 0.0373(6) 0.0744(10) 0.0036(6) 0.0053(8) 0.0047(6) C17 0.0506(8) 0.0505(8) 0.0685(10) 0.0053(7) 0.0063(7) -0.0078(6) C18 0.0644(13) 0.125(2) 0.126(2) 0.0076(18) -0.0252(14) -0.0219(14) C19 0.0631(9) 0.0337(6) 0.0604(8) -0.0078(6) -0.0166(7) 0.0008(5) C20 0.0475(7) 0.0318(5) 0.0471(7) -0.0009(5) 0.0007(6) 0.0049(5) C21 0.0405(7) 0.0382(6) 0.0574(8) 0.0046(6) -0.0002(6) 0.0040(5) C22 0.0735(11) 0.0431(7) 0.0659(10) -0.0031(7) 0.0184(9) 0.0145(7) N1 0.0342(5) 0.0455(6) 0.0769(9) 0.0002(6) -0.0111(5) -0.0013(5) N2 0.0434(6) 0.0364(5) 0.0521(6) 0.0013(5) 0.0097(5) -0.0008(4) N3 0.0628(8) 0.0565(8) 0.0690(9) 0.0179(7) -0.0036(7) 0.0041(6) O1 0.0798(8) 0.0691(8) 0.0915(10) -0.0077(7) -0.0522(8) 0.0058(6) O2 0.0395(5) 0.0532(5) 0.0647(6) 0.0032(5) 0.0070(5) 0.0043(4) O3 0.0778(9) 0.1113(12) 0.0610(8) -0.0053(7) 0.0058(7) -0.0306(8) O4 0.0491(6) 0.1046(11) 0.0970(11) 0.0145(8) -0.0010(7) -0.0208(7) _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 C1 O1 1.2206(18) . ? C1 N1 1.361(2) . ? C1 C2 1.509(2) . ? C2 C11 1.531(2) . ? C2 C19 1.5656(19) . ? C2 C3 1.5714(18) . ? C3 C4 1.5184(16) . ? C3 C12 1.5332(17) . ? C3 C20 1.5968(16) . ? C4 C5 1.3926(17) . ? C4 C9 1.4008(17) . ? C5 C6 1.382(2) . ? C5 H5 0.9300 . ? C6 C7 1.376(3) . ? C6 H6 0.9300 . ? C7 C8 1.368(3) . ? C7 H7 0.9300 . ? C8 C9 1.395(2) . ? C8 H8 0.9300 . ? C9 N1 1.4172(18) . ? C10 N1 1.470(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O2 1.2303(16) . ? C12 N2 1.3428(17) . ? C13 N2 1.4628(18) . ? C13 C17 1.506(2) . ? C13 C14 1.537(2) . ? C13 H13 0.9800 . ? C14 C15 1.513(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.503(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N2 1.4785(19) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.187(2) . ? C17 O4 1.337(2) . ? C18 O4 1.433(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.554(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.467(2) . ? C20 C22 1.539(2) . ? C21 N3 1.138(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C1 N1 121.25(15) . . ? O1 C1 C2 120.04(16) . . ? N1 C1 C2 118.46(12) . . ? C1 C2 C11 110.14(14) . . ? C1 C2 C19 109.09(13) . . ? C11 C2 C19 113.45(13) . . ? C1 C2 C3 118.82(11) . . ? C11 C2 C3 115.42(14) . . ? C19 C2 C3 88.00(9) . . ? C4 C3 C12 106.99(9) . . ? C4 C3 C2 112.20(10) . . ? C12 C3 C2 121.39(11) . . ? C4 C3 C20 111.78(10) . . ? C12 C3 C20 115.41(10) . . ? C2 C3 C20 88.19(9) . . ? C5 C4 C9 118.86(12) . . ? C5 C4 C3 118.52(11) . . ? C9 C4 C3 122.60(11) . . ? C6 C5 C4 121.34(14) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 119.17(14) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C6 120.77(14) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.86(14) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 118.99(13) . . ? C8 C9 N1 119.60(13) . . ? C4 C9 N1 121.36(12) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 N2 121.40(12) . . ? O2 C12 C3 120.27(11) . . ? N2 C12 C3 118.24(11) . . ? N2 C13 C17 111.81(12) . . ? N2 C13 C14 102.82(13) . . ? C17 C13 C14 110.58(14) . . ? N2 C13 H13 110.5 . . ? C17 C13 H13 110.5 . . ? C14 C13 H13 110.5 . . ? C15 C14 C13 103.65(12) . . ? C15 C14 H14A 111.0 . . ? C13 C14 H14A 111.0 . . ? C15 C14 H14B 111.0 . . ? C13 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? C16 C15 C14 104.60(14) . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15A 110.8 . . ? C16 C15 H15B 110.8 . . ? C14 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? N2 C16 C15 103.88(13) . . ? N2 C16 H16A 111.0 . . ? C15 C16 H16A 111.0 . . ? N2 C16 H16B 111.0 . . ? C15 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? O3 C17 O4 124.01(16) . . ? O3 C17 C13 126.33(15) . . ? O4 C17 C13 109.50(14) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C2 89.94(10) . . ? C20 C19 H19A 113.7 . . ? C2 C19 H19A 113.7 . . ? C20 C19 H19B 113.7 . . ? C2 C19 H19B 113.7 . . ? H19A C19 H19B 110.9 . . ? C21 C20 C22 107.07(12) . . ? C21 C20 C19 114.77(12) . . ? C22 C20 C19 112.80(13) . . ? C21 C20 C3 114.45(11) . . ? C22 C20 C3 119.55(12) . . ? C19 C20 C3 87.50(9) . . ? N3 C21 C20 177.57(15) . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C9 123.63(12) . . ? C1 N1 C10 117.32(14) . . ? C9 N1 C10 118.95(15) . . ? C12 N2 C13 119.02(12) . . ? C12 N2 C16 128.17(11) . . ? C13 N2 C16 111.99(11) . . ? C17 O4 C18 116.96(17) . . ? 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 O1 C1 C2 C11 28.48(19) . . . . ? N1 C1 C2 C11 -157.19(14) . . . . ? O1 C1 C2 C19 -96.65(17) . . . . ? N1 C1 C2 C19 77.69(15) . . . . ? O1 C1 C2 C3 164.82(14) . . . . ? N1 C1 C2 C3 -20.84(19) . . . . ? C1 C2 C3 C4 16.61(16) . . . . ? C11 C2 C3 C4 150.75(12) . . . . ? C19 C2 C3 C4 -94.14(12) . . . . ? C1 C2 C3 C12 -111.63(14) . . . . ? C11 C2 C3 C12 22.52(17) . . . . ? C19 C2 C3 C12 137.62(12) . . . . ? C1 C2 C3 C20 129.45(13) . . . . ? C11 C2 C3 C20 -96.41(13) . . . . ? C19 C2 C3 C20 18.70(11) . . . . ? C12 C3 C4 C5 -48.29(14) . . . . ? C2 C3 C4 C5 176.23(11) . . . . ? C20 C3 C4 C5 78.97(14) . . . . ? C12 C3 C4 C9 129.94(12) . . . . ? C2 C3 C4 C9 -5.55(16) . . . . ? C20 C3 C4 C9 -102.81(13) . . . . ? C9 C4 C5 C6 1.64(19) . . . . ? C3 C4 C5 C6 179.93(12) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C6 C7 C8 C9 0.4(2) . . . . ? C7 C8 C9 C4 0.7(2) . . . . ? C7 C8 C9 N1 -176.88(13) . . . . ? C5 C4 C9 C8 -1.65(18) . . . . ? C3 C4 C9 C8 -179.87(11) . . . . ? C5 C4 C9 N1 175.87(11) . . . . ? C3 C4 C9 N1 -2.35(18) . . . . ? C4 C3 C12 O2 102.50(13) . . . . ? C2 C3 C12 O2 -127.00(13) . . . . ? C20 C3 C12 O2 -22.58(17) . . . . ? C4 C3 C12 N2 -73.90(13) . . . . ? C2 C3 C12 N2 56.60(15) . . . . ? C20 C3 C12 N2 161.01(11) . . . . ? N2 C13 C14 C15 30.72(17) . . . . ? C17 C13 C14 C15 -88.79(16) . . . . ? C13 C14 C15 C16 -36.65(19) . . . . ? C14 C15 C16 N2 27.72(18) . . . . ? N2 C13 C17 O3 -26.2(3) . . . . ? C14 C13 C17 O3 87.8(2) . . . . ? N2 C13 C17 O4 158.30(14) . . . . ? C14 C13 C17 O4 -87.77(17) . . . . ? C1 C2 C19 C20 -139.11(12) . . . . ? C11 C2 C19 C20 97.71(15) . . . . ? C3 C2 C19 C20 -19.22(11) . . . . ? C2 C19 C20 C21 134.77(12) . . . . ? C2 C19 C20 C22 -102.23(13) . . . . ? C2 C19 C20 C3 18.91(11) . . . . ? C4 C3 C20 C21 -21.77(15) . . . . ? C12 C3 C20 C21 100.80(13) . . . . ? C2 C3 C20 C21 -135.01(12) . . . . ? C4 C3 C20 C22 -150.70(13) . . . . ? C12 C3 C20 C22 -28.13(18) . . . . ? C2 C3 C20 C22 96.06(14) . . . . ? C4 C3 C20 C19 94.39(12) . . . . ? C12 C3 C20 C19 -143.04(12) . . . . ? C2 C3 C20 C19 -18.85(11) . . . . ? C22 C20 C21 N3 -8(4) . . . . ? C19 C20 C21 N3 118(4) . . . . ? C3 C20 C21 N3 -143(4) . . . . ? O1 C1 N1 C9 -172.79(14) . . . . ? C2 C1 N1 C9 13.0(2) . . . . ? O1 C1 N1 C10 3.4(2) . . . . ? C2 C1 N1 C10 -170.84(15) . . . . ? C8 C9 N1 C1 176.29(13) . . . . ? C4 C9 N1 C1 -1.21(19) . . . . ? C8 C9 N1 C10 0.1(2) . . . . ? C4 C9 N1 C10 -177.36(15) . . . . ? O2 C12 N2 C13 -0.89(19) . . . . ? C3 C12 N2 C13 175.47(11) . . . . ? O2 C12 N2 C16 -169.64(14) . . . . ? C3 C12 N2 C16 6.7(2) . . . . ? C17 C13 N2 C12 -65.92(17) . . . . ? C14 C13 N2 C12 175.44(12) . . . . ? C17 C13 N2 C16 104.56(15) . . . . ? C14 C13 N2 C16 -14.08(16) . . . . ? C15 C16 N2 C12 161.09(14) . . . . ? C15 C16 N2 C13 -8.31(18) . . . . ? O3 C17 O4 C18 0.2(3) . . . . ? C13 C17 O4 C18 175.83(19) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.225 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037