data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N3 O5, C H4 O' _chemical_formula_sum 'C24 H29 N3 O6' _chemical_formula_weight 455.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 23.002(2) _cell_length_b 7.7747(8) _cell_length_c 25.097(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4488.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 645 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 68.22 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.806 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7082 _exptl_absorpt_correction_T_max 0.7941 _exptl_absorpt_process_details 'NUMABS by T.Higashi Jun 3, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19556 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 68.24 _reflns_number_total 4084 _reflns_number_gt 3515 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_cell_refinement 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_data_reduction 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0365P)^2^+3.0959P] 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 4084 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 -0.02776(6) 0.3153(2) 0.15074(6) 0.0437(4) Uani 1 1 d . . . O2 O 0.05935(5) 0.21931(18) 0.12638(5) 0.0326(3) Uani 1 1 d . . . O3 O 0.21623(5) 0.66225(17) 0.26540(5) 0.0314(3) Uani 1 1 d . . . O4 O 0.13554(5) 0.79003(16) 0.23352(5) 0.0281(3) Uani 1 1 d . . . O5 O 0.01018(6) 0.2496(2) 0.41346(5) 0.0419(4) Uani 1 1 d . . . O6 O 0.06514(7) 0.6173(2) 0.00814(6) 0.0524(4) Uani 1 1 d . . . H6 H 0.0373 0.6502 0.0273 0.063 Uiso 1 1 d R . . N1 N 0.11103(6) 0.22846(18) 0.30866(6) 0.0231(3) Uani 1 1 d . . . N2 N 0.05765(6) 0.27815(19) 0.33381(6) 0.0241(3) Uani 1 1 d . . . N3 N 0.25021(9) 0.6844(3) 0.54528(7) 0.0500(5) Uani 1 1 d . . . C1 C 0.01041(7) 0.3410(2) 0.30468(7) 0.0262(4) Uani 1 1 d . . . H1A H -0.0240 0.3596 0.3247 0.031 Uiso 1 1 calc R . . C2 C 0.00641(7) 0.3787(2) 0.25313(7) 0.0266(4) Uani 1 1 d . . . H2A H -0.0306 0.4198 0.2421 0.032 Uiso 1 1 calc R . . C3 C 0.05022(7) 0.3667(2) 0.21035(7) 0.0238(4) Uani 1 1 d . . . C4 C 0.10536(7) 0.4266(2) 0.21458(7) 0.0223(4) Uani 1 1 d . . . C5 C 0.12361(7) 0.5111(2) 0.26662(7) 0.0214(4) Uani 1 1 d . . . H5A H 0.0881 0.5574 0.2845 0.026 Uiso 1 1 calc R . . C6 C 0.15181(7) 0.3778(2) 0.30385(7) 0.0220(4) Uani 1 1 d . . . H6A H 0.1874 0.3345 0.2853 0.026 Uiso 1 1 calc R . . C7 C 0.02355(7) 0.2995(2) 0.16000(7) 0.0265(4) Uani 1 1 d . . . C8 C 0.03371(9) 0.1688(3) 0.07539(8) 0.0379(5) Uani 1 1 d . . . H8A H 0.0160 0.2700 0.0578 0.045 Uiso 1 1 calc R . . H8B H 0.0029 0.0817 0.0812 0.045 Uiso 1 1 calc R . . C9 C 0.08047(11) 0.0961(3) 0.04124(9) 0.0518(6) Uani 1 1 d . . . H9A H 0.0650 0.0728 0.0056 0.078 Uiso 1 1 calc R . . H9B H 0.0948 -0.0111 0.0570 0.078 Uiso 1 1 calc R . . H9C H 0.1125 0.1789 0.0386 0.078 Uiso 1 1 calc R . . C10 C 0.15335(7) 0.4108(2) 0.17419(7) 0.0283(4) Uani 1 1 d . . . H10A H 0.1406 0.3361 0.1450 0.042 Uiso 1 1 calc R . . H10B H 0.1878 0.3611 0.1912 0.042 Uiso 1 1 calc R . . H10C H 0.1629 0.5250 0.1601 0.042 Uiso 1 1 calc R . . C11 C 0.16478(7) 0.6602(2) 0.25573(7) 0.0225(4) Uani 1 1 d . . . C12 C 0.16840(8) 0.9415(2) 0.21641(8) 0.0316(4) Uani 1 1 d . . . H12A H 0.2038 0.9536 0.2385 0.038 Uiso 1 1 calc R . . H12B H 0.1444 1.0460 0.2212 0.038 Uiso 1 1 calc R . . C13 C 0.18516(9) 0.9235(3) 0.15904(8) 0.0402(5) Uani 1 1 d . . . H13A H 0.2045 1.0290 0.1471 0.060 Uiso 1 1 calc R . . H13B H 0.1502 0.9039 0.1375 0.060 Uiso 1 1 calc R . . H13C H 0.2117 0.8259 0.1550 0.060 Uiso 1 1 calc R . . C14 C 0.17168(7) 0.4517(2) 0.35675(7) 0.0221(4) Uani 1 1 d . . . C15 C 0.22627(7) 0.4056(2) 0.37648(7) 0.0243(4) Uani 1 1 d . . . H15A H 0.2508 0.3332 0.3559 0.029 Uiso 1 1 calc R . . C16 C 0.24516(8) 0.4635(2) 0.42541(7) 0.0268(4) Uani 1 1 d . . . H16A H 0.2826 0.4320 0.4381 0.032 Uiso 1 1 calc R . . C17 C 0.20930(8) 0.5683(2) 0.45622(7) 0.0274(4) Uani 1 1 d . . . C18 C 0.15462(8) 0.6168(2) 0.43706(7) 0.0274(4) Uani 1 1 d . . . H18A H 0.1299 0.6878 0.4580 0.033 Uiso 1 1 calc R . . C19 C 0.13672(7) 0.5604(2) 0.38732(7) 0.0255(4) Uani 1 1 d . . . H19A H 0.1001 0.5962 0.3738 0.031 Uiso 1 1 calc R . . C20 C 0.23085(8) 0.6318(3) 0.50661(8) 0.0338(4) Uani 1 1 d . . . C21 C 0.13328(8) 0.0897(2) 0.34417(7) 0.0269(4) Uani 1 1 d . . . H21A H 0.1762 0.0941 0.3462 0.032 Uiso 1 1 calc R . . H21B H 0.1216 -0.0246 0.3304 0.032 Uiso 1 1 calc R . . C22 C 0.10657(8) 0.1212(3) 0.39902(7) 0.0314(4) Uani 1 1 d . . . H22A H 0.0968 0.0116 0.4169 0.038 Uiso 1 1 calc R . . H22B H 0.1331 0.1883 0.4221 0.038 Uiso 1 1 calc R . . C23 C 0.05272(8) 0.2222(3) 0.38562(7) 0.0300(4) Uani 1 1 d . . . C24 C 0.10793(10) 0.5799(3) 0.04593(10) 0.0542(6) Uani 1 1 d . . . H24A H 0.1262 0.6871 0.0579 0.081 Uiso 1 1 calc R . . H24B H 0.1375 0.5052 0.0299 0.081 Uiso 1 1 calc R . . H24C H 0.0902 0.5213 0.0764 0.081 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 0.0249(7) 0.0603(10) 0.0461(9) -0.0182(7) -0.0115(6) 0.0058(7) O2 0.0278(7) 0.0437(8) 0.0264(7) -0.0082(6) -0.0037(5) -0.0004(6) O3 0.0202(6) 0.0336(7) 0.0404(8) 0.0042(6) -0.0040(5) -0.0038(5) O4 0.0240(6) 0.0249(7) 0.0353(7) 0.0052(5) -0.0010(5) -0.0019(5) O5 0.0362(8) 0.0542(10) 0.0353(8) 0.0095(7) 0.0126(6) 0.0030(7) O6 0.0498(9) 0.0742(12) 0.0332(8) -0.0020(8) 0.0059(7) 0.0135(9) N1 0.0183(7) 0.0232(7) 0.0279(8) 0.0019(6) 0.0017(6) 0.0005(6) N2 0.0192(7) 0.0276(8) 0.0256(8) 0.0022(6) 0.0034(6) -0.0020(6) N3 0.0567(11) 0.0604(13) 0.0329(10) -0.0070(9) -0.0074(9) -0.0019(10) C1 0.0162(8) 0.0317(10) 0.0308(10) 0.0007(8) 0.0019(7) -0.0010(7) C2 0.0176(8) 0.0301(10) 0.0319(10) -0.0007(8) -0.0016(7) -0.0002(7) C3 0.0212(8) 0.0248(9) 0.0254(9) 0.0007(7) -0.0024(7) 0.0006(7) C4 0.0223(8) 0.0215(8) 0.0231(9) 0.0008(7) -0.0002(7) 0.0006(7) C5 0.0174(8) 0.0236(9) 0.0233(9) 0.0000(7) 0.0006(6) -0.0009(7) C6 0.0179(8) 0.0237(9) 0.0244(9) 0.0003(7) 0.0009(7) -0.0014(7) C7 0.0248(9) 0.0255(9) 0.0293(10) 0.0012(8) -0.0023(7) -0.0017(7) C8 0.0398(11) 0.0468(13) 0.0270(11) -0.0089(9) -0.0075(8) -0.0046(10) C9 0.0570(14) 0.0621(16) 0.0363(13) -0.0154(11) -0.0022(11) 0.0036(12) C10 0.0235(9) 0.0344(10) 0.0270(10) -0.0026(8) 0.0021(7) -0.0048(8) C11 0.0228(9) 0.0240(9) 0.0207(9) -0.0022(7) 0.0011(7) -0.0006(7) C12 0.0336(10) 0.0227(9) 0.0386(11) 0.0052(8) 0.0026(8) -0.0033(8) C13 0.0425(12) 0.0393(12) 0.0388(12) 0.0062(9) 0.0037(9) -0.0026(10) C14 0.0218(8) 0.0218(8) 0.0229(9) 0.0028(7) 0.0008(7) -0.0037(7) C15 0.0224(8) 0.0236(9) 0.0268(9) 0.0016(7) 0.0011(7) -0.0007(7) C16 0.0248(9) 0.0277(10) 0.0280(10) 0.0043(8) -0.0031(7) -0.0019(7) C17 0.0319(9) 0.0280(9) 0.0223(9) 0.0034(7) -0.0026(7) -0.0044(8) C18 0.0290(9) 0.0264(9) 0.0268(9) -0.0005(8) 0.0052(7) -0.0004(7) C19 0.0229(8) 0.0262(9) 0.0273(10) 0.0021(7) 0.0000(7) -0.0003(7) C20 0.0380(11) 0.0352(11) 0.0284(10) 0.0006(9) -0.0014(8) -0.0010(9) C21 0.0260(9) 0.0230(9) 0.0316(10) 0.0037(8) -0.0020(7) 0.0000(7) C22 0.0328(10) 0.0316(10) 0.0298(10) 0.0061(8) -0.0024(8) -0.0016(8) C23 0.0293(9) 0.0319(10) 0.0287(10) 0.0020(8) 0.0038(8) -0.0038(8) C24 0.0474(13) 0.0530(15) 0.0622(16) 0.0107(12) -0.0029(12) 0.0015(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.209(2) . ? O2 C7 1.334(2) . ? O2 C8 1.463(2) . ? O3 C11 1.208(2) . ? O4 C11 1.335(2) . ? O4 C12 1.464(2) . ? O5 C23 1.221(2) . ? O6 C24 1.397(3) . ? O6 H6 0.8400 . ? N1 N2 1.4336(19) . ? N1 C21 1.490(2) . ? N1 C6 1.498(2) . ? N2 C23 1.376(2) . ? N2 C1 1.398(2) . ? N3 C20 1.143(2) . ? C1 C2 1.330(3) . ? C1 H1A 0.9500 . ? C2 C3 1.475(2) . ? C2 H2A 0.9500 . ? C3 C4 1.355(2) . ? C3 C7 1.499(2) . ? C4 C10 1.504(2) . ? C4 C5 1.521(2) . ? C5 C11 1.522(2) . ? C5 C6 1.538(2) . ? C5 H5A 1.0000 . ? C6 C14 1.517(2) . ? C6 H6A 1.0000 . ? C8 C9 1.487(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 C13 1.497(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.396(2) . ? C14 C15 1.396(2) . ? C15 C16 1.378(2) . ? C15 H15A 0.9500 . ? C16 C17 1.394(3) . ? C16 H16A 0.9500 . ? C17 C18 1.398(3) . ? C17 C20 1.445(3) . ? C18 C19 1.386(2) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C21 C22 1.527(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.505(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C7 O2 C8 115.48(14) . . ? C11 O4 C12 118.07(13) . . ? C24 O6 H6 102.2 . . ? N2 N1 C21 103.07(12) . . ? N2 N1 C6 111.28(13) . . ? C21 N1 C6 113.24(13) . . ? C23 N2 C1 122.74(14) . . ? C23 N2 N1 113.68(14) . . ? C1 N2 N1 121.98(14) . . ? C2 C1 N2 129.77(16) . . ? C2 C1 H1A 115.1 . . ? N2 C1 H1A 115.1 . . ? C1 C2 C3 130.31(16) . . ? C1 C2 H2A 114.8 . . ? C3 C2 H2A 114.8 . . ? C4 C3 C2 124.11(16) . . ? C4 C3 C7 124.67(16) . . ? C2 C3 C7 110.84(14) . . ? C3 C4 C10 127.34(16) . . ? C3 C4 C5 118.28(15) . . ? C10 C4 C5 114.28(14) . . ? C4 C5 C11 110.28(13) . . ? C4 C5 C6 110.31(14) . . ? C11 C5 C6 111.08(13) . . ? C4 C5 H5A 108.4 . . ? C11 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? N1 C6 C14 114.30(13) . . ? N1 C6 C5 107.88(13) . . ? C14 C6 C5 113.82(14) . . ? N1 C6 H6A 106.8 . . ? C14 C6 H6A 106.8 . . ? C5 C6 H6A 106.8 . . ? O1 C7 O2 121.90(17) . . ? O1 C7 C3 121.76(17) . . ? O2 C7 C3 116.34(14) . . ? O2 C8 C9 108.34(16) . . ? O2 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? O2 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 124.59(16) . . ? O3 C11 C5 125.69(16) . . ? O4 C11 C5 109.72(13) . . ? O4 C12 C13 109.89(16) . . ? O4 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? O4 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.57(16) . . ? C19 C14 C6 122.44(15) . . ? C15 C14 C6 118.96(15) . . ? C16 C15 C14 121.05(17) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C15 C16 C17 119.91(17) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C17 C18 119.94(16) . . ? C16 C17 C20 118.83(17) . . ? C18 C17 C20 121.17(17) . . ? C19 C18 C17 119.47(17) . . ? C19 C18 H18A 120.3 . . ? C17 C18 H18A 120.3 . . ? C18 C19 C14 121.02(16) . . ? C18 C19 H19A 119.5 . . ? C14 C19 H19A 119.5 . . ? N3 C20 C17 176.8(2) . . ? N1 C21 C22 106.53(14) . . ? N1 C21 H21A 110.4 . . ? C22 C21 H21A 110.4 . . ? N1 C21 H21B 110.4 . . ? C22 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? C23 C22 C21 102.33(14) . . ? C23 C22 H22A 111.3 . . ? C21 C22 H22A 111.3 . . ? C23 C22 H22B 111.3 . . ? C21 C22 H22B 111.3 . . ? H22A C22 H22B 109.2 . . ? O5 C23 N2 123.49(17) . . ? O5 C23 C22 128.52(17) . . ? N2 C23 C22 107.95(15) . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 N1 N2 C23 16.22(18) . . . . ? C6 N1 N2 C23 -105.45(16) . . . . ? C21 N1 N2 C1 -149.67(16) . . . . ? C6 N1 N2 C1 88.66(18) . . . . ? C23 N2 C1 C2 -170.46(19) . . . . ? N1 N2 C1 C2 -5.8(3) . . . . ? N2 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -47.3(3) . . . . ? C1 C2 C3 C7 139.5(2) . . . . ? C2 C3 C4 C10 176.36(17) . . . . ? C7 C3 C4 C10 -11.4(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C7 C3 C4 C5 172.46(16) . . . . ? C3 C4 C5 C11 -143.70(16) . . . . ? C10 C4 C5 C11 39.6(2) . . . . ? C3 C4 C5 C6 93.23(18) . . . . ? C10 C4 C5 C6 -83.44(17) . . . . ? N2 N1 C6 C14 63.52(17) . . . . ? C21 N1 C6 C14 -52.02(18) . . . . ? N2 N1 C6 C5 -64.16(16) . . . . ? C21 N1 C6 C5 -179.70(13) . . . . ? C4 C5 C6 N1 -52.36(17) . . . . ? C11 C5 C6 N1 -174.96(13) . . . . ? C4 C5 C6 C14 179.68(13) . . . . ? C11 C5 C6 C14 57.08(18) . . . . ? C8 O2 C7 O1 6.3(3) . . . . ? C8 O2 C7 C3 -174.58(16) . . . . ? C4 C3 C7 O1 -148.2(2) . . . . ? C2 C3 C7 O1 25.0(2) . . . . ? C4 C3 C7 O2 32.7(3) . . . . ? C2 C3 C7 O2 -154.12(16) . . . . ? C7 O2 C8 C9 174.96(18) . . . . ? C12 O4 C11 O3 4.2(3) . . . . ? C12 O4 C11 C5 -175.65(14) . . . . ? C4 C5 C11 O3 -108.86(19) . . . . ? C6 C5 C11 O3 13.8(2) . . . . ? C4 C5 C11 O4 70.96(17) . . . . ? C6 C5 C11 O4 -166.42(13) . . . . ? C11 O4 C12 C13 92.86(19) . . . . ? N1 C6 C14 C19 -78.3(2) . . . . ? C5 C6 C14 C19 46.3(2) . . . . ? N1 C6 C14 C15 99.84(17) . . . . ? C5 C6 C14 C15 -135.58(16) . . . . ? C19 C14 C15 C16 1.0(3) . . . . ? C6 C14 C15 C16 -177.18(16) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C15 C16 C17 C20 -178.03(17) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C20 C17 C18 C19 176.67(17) . . . . ? C17 C18 C19 C14 2.0(3) . . . . ? C15 C14 C19 C18 -2.3(3) . . . . ? C6 C14 C19 C18 175.79(16) . . . . ? C16 C17 C20 N3 49(4) . . . . ? C18 C17 C20 N3 -128(4) . . . . ? N2 N1 C21 C22 -24.60(17) . . . . ? C6 N1 C21 C22 95.73(16) . . . . ? N1 C21 C22 C23 24.06(18) . . . . ? C1 N2 C23 O5 -13.2(3) . . . . ? N1 N2 C23 O5 -179.01(17) . . . . ? C1 N2 C23 C22 164.87(16) . . . . ? N1 N2 C23 C22 -0.9(2) . . . . ? C21 C22 C23 O5 163.6(2) . . . . ? C21 C22 C23 N2 -14.40(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O5 0.84 2.00 2.816(2) 163.5 3 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.189 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.044