data_sa851 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N3 O5' _chemical_formula_sum 'C16 H17 N3 O5' _chemical_formula_weight 331.33 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3908(14) _cell_length_b 9.8594(15) _cell_length_c 10.8783(17) _cell_angle_alpha 65.913(8) _cell_angle_beta 75.686(11) _cell_angle_gamma 75.628(11) _cell_volume 785.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 315 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9549 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10503 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3581 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0427P)^2^+0.3475P] 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 3581 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 0.63378(16) 0.79458(16) 0.76588(12) 0.0381(3) Uani 1 1 d . . . O2 O 0.21480(17) 0.60469(15) 0.44891(13) 0.0402(3) Uani 1 1 d . . . O3 O 0.31768(16) 0.72064(14) 0.22925(12) 0.0339(3) Uani 1 1 d . . . O4 O 1.02090(17) 0.70705(16) -0.17352(13) 0.0440(4) Uani 1 1 d . . . O5 O 0.93951(18) 0.94766(16) -0.23845(13) 0.0419(3) Uani 1 1 d . . . N1 N 0.56271(17) 0.80064(16) 0.57318(13) 0.0265(3) Uani 1 1 d . . . N2 N 0.63390(17) 0.82930(16) 0.43209(13) 0.0248(3) Uani 1 1 d . . . N3 N 0.93857(18) 0.81947(18) -0.15244(15) 0.0331(3) Uani 1 1 d . . . C1 C 0.56235(19) 0.74337(18) 0.38099(16) 0.0234(3) Uani 1 1 d . . . H1A H 0.5807 0.6342 0.4407 0.028 Uiso 1 1 calc R . . C2 C 0.3723(2) 0.80313(18) 0.38840(16) 0.0259(3) Uani 1 1 d . . . H2A H 0.3537 0.9065 0.3171 0.031 Uiso 1 1 calc R . . C3 C 0.2986(2) 0.8103(2) 0.52698(17) 0.0297(4) Uani 1 1 d . . . H3A H 0.1813 0.8172 0.5554 0.036 Uiso 1 1 calc R . . C4 C 0.3914(2) 0.8072(2) 0.61078(17) 0.0295(4) Uani 1 1 d . . . H4A H 0.3396 0.8096 0.6982 0.035 Uiso 1 1 calc R . . C5 C 0.6714(2) 0.79777(19) 0.64893(17) 0.0289(4) Uani 1 1 d . . . C6 C 0.8410(2) 0.8000(2) 0.56003(18) 0.0305(4) Uani 1 1 d . . . H6A H 0.9255 0.7194 0.6091 0.037 Uiso 1 1 calc R . . H6B H 0.8770 0.8985 0.5305 0.037 Uiso 1 1 calc R . . C7 C 0.8155(2) 0.7731(2) 0.43823(17) 0.0287(4) Uani 1 1 d . . . H7A H 0.8847 0.8301 0.3532 0.034 Uiso 1 1 calc R . . H7B H 0.8442 0.6647 0.4526 0.034 Uiso 1 1 calc R . . C8 C 0.2907(2) 0.69912(18) 0.36130(17) 0.0275(4) Uani 1 1 d . . . C9 C 0.2619(3) 0.6149(2) 0.1939(2) 0.0466(5) Uani 1 1 d . . . H9A H 0.1396 0.6200 0.2220 0.056 Uiso 1 1 calc R . . H9B H 0.3163 0.5108 0.2416 0.056 Uiso 1 1 calc R . . C10 C 0.3069(4) 0.6554(3) 0.0435(2) 0.0618(7) Uani 1 1 d . . . H10A H 0.2799 0.5797 0.0186 0.093 Uiso 1 1 calc R . . H10B H 0.4266 0.6589 0.0156 0.093 Uiso 1 1 calc R . . H10C H 0.2438 0.7544 -0.0028 0.093 Uiso 1 1 calc R . . C11 C 0.6544(2) 0.76297(18) 0.23837(16) 0.0247(3) Uani 1 1 d . . . C12 C 0.7442(2) 0.63830(19) 0.20835(17) 0.0292(4) Uani 1 1 d . . . H12A H 0.7428 0.5402 0.2768 0.035 Uiso 1 1 calc R . . C13 C 0.8359(2) 0.6558(2) 0.07920(17) 0.0310(4) Uani 1 1 d . . . H13A H 0.8971 0.5709 0.0581 0.037 Uiso 1 1 calc R . . C14 C 0.8357(2) 0.79987(19) -0.01768(16) 0.0278(4) Uani 1 1 d . . . C15 C 0.7457(2) 0.92575(19) 0.00772(17) 0.0304(4) Uani 1 1 d . . . H15A H 0.7460 1.0233 -0.0617 0.036 Uiso 1 1 calc R . . C16 C 0.6546(2) 0.90663(19) 0.13719(17) 0.0293(4) Uani 1 1 d . . . H16A H 0.5920 0.9919 0.1570 0.035 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 0.0396(7) 0.0524(8) 0.0279(7) -0.0191(6) -0.0047(5) -0.0105(6) O2 0.0469(8) 0.0398(7) 0.0344(7) -0.0086(6) -0.0029(6) -0.0211(6) O3 0.0452(8) 0.0337(7) 0.0283(6) -0.0102(5) -0.0095(5) -0.0150(6) O4 0.0436(8) 0.0515(9) 0.0300(7) -0.0198(6) -0.0012(6) 0.0072(6) O5 0.0480(8) 0.0463(8) 0.0263(7) -0.0090(6) 0.0026(6) -0.0157(6) N1 0.0249(7) 0.0335(7) 0.0223(7) -0.0121(6) -0.0015(5) -0.0061(6) N2 0.0242(7) 0.0307(7) 0.0212(7) -0.0114(6) -0.0001(5) -0.0078(6) N3 0.0298(8) 0.0442(9) 0.0253(7) -0.0138(7) -0.0035(6) -0.0055(7) C1 0.0247(8) 0.0238(8) 0.0216(7) -0.0085(6) -0.0028(6) -0.0047(6) C2 0.0257(8) 0.0259(8) 0.0254(8) -0.0081(6) -0.0048(6) -0.0046(6) C3 0.0234(8) 0.0355(9) 0.0306(9) -0.0149(7) 0.0000(7) -0.0054(7) C4 0.0265(8) 0.0359(9) 0.0274(8) -0.0147(7) 0.0006(7) -0.0072(7) C5 0.0314(9) 0.0304(9) 0.0269(8) -0.0111(7) -0.0064(7) -0.0056(7) C6 0.0270(9) 0.0369(9) 0.0306(9) -0.0137(7) -0.0059(7) -0.0074(7) C7 0.0234(8) 0.0357(9) 0.0290(9) -0.0137(7) -0.0019(6) -0.0075(7) C8 0.0275(8) 0.0261(8) 0.0273(8) -0.0065(7) -0.0076(7) -0.0044(7) C9 0.0626(14) 0.0454(12) 0.0445(12) -0.0179(9) -0.0136(10) -0.0237(10) C10 0.0804(18) 0.0734(17) 0.0527(14) -0.0367(13) -0.0076(13) -0.0296(14) C11 0.0253(8) 0.0272(8) 0.0231(8) -0.0099(6) -0.0041(6) -0.0059(6) C12 0.0339(9) 0.0250(8) 0.0265(8) -0.0083(7) -0.0039(7) -0.0041(7) C13 0.0330(9) 0.0306(9) 0.0289(9) -0.0143(7) -0.0032(7) -0.0005(7) C14 0.0270(8) 0.0363(9) 0.0205(8) -0.0116(7) -0.0015(6) -0.0063(7) C15 0.0365(9) 0.0288(9) 0.0225(8) -0.0062(7) -0.0036(7) -0.0067(7) C16 0.0348(9) 0.0256(8) 0.0257(8) -0.0099(7) -0.0023(7) -0.0040(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 O1 C5 1.222(2) . ? O2 C8 1.205(2) . ? O3 C8 1.332(2) . ? O3 C9 1.454(2) . ? O4 N3 1.228(2) . ? O5 N3 1.228(2) . ? N1 C5 1.360(2) . ? N1 C4 1.387(2) . ? N1 N2 1.4383(18) . ? N2 C1 1.480(2) . ? N2 C7 1.495(2) . ? N3 C14 1.469(2) . ? C1 C11 1.509(2) . ? C1 C2 1.551(2) . ? C1 H1A 1.0000 . ? C2 C3 1.505(2) . ? C2 C8 1.517(2) . ? C2 H2A 1.0000 . ? C3 C4 1.325(2) . ? C3 H3A 0.9500 . ? C4 H4A 0.9500 . ? C5 C6 1.510(2) . ? C6 C7 1.525(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 C10 1.488(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.390(2) . ? C11 C16 1.395(2) . ? C12 C13 1.389(2) . ? C12 H12A 0.9500 . ? C13 C14 1.381(2) . ? C13 H13A 0.9500 . ? C14 C15 1.378(2) . ? C15 C16 1.388(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? 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 C8 O3 C9 116.53(14) . . ? C5 N1 C4 126.95(14) . . ? C5 N1 N2 113.49(13) . . ? C4 N1 N2 118.35(13) . . ? N1 N2 C1 109.20(12) . . ? N1 N2 C7 102.42(12) . . ? C1 N2 C7 112.26(13) . . ? O4 N3 O5 123.01(15) . . ? O4 N3 C14 118.47(15) . . ? O5 N3 C14 118.51(15) . . ? N2 C1 C11 107.21(12) . . ? N2 C1 C2 107.94(13) . . ? C11 C1 C2 113.83(13) . . ? N2 C1 H1A 109.3 . . ? C11 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? C3 C2 C8 110.46(14) . . ? C3 C2 C1 109.75(13) . . ? C8 C2 C1 109.03(13) . . ? C3 C2 H2A 109.2 . . ? C8 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C4 C3 C2 122.41(15) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C3 C4 N1 121.17(15) . . ? C3 C4 H4A 119.4 . . ? N1 C4 H4A 119.4 . . ? O1 C5 N1 125.03(16) . . ? O1 C5 C6 128.40(16) . . ? N1 C5 C6 106.57(14) . . ? C5 C6 C7 103.92(14) . . ? C5 C6 H6A 111.0 . . ? C7 C6 H6A 111.0 . . ? C5 C6 H6B 111.0 . . ? C7 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? N2 C7 C6 103.93(13) . . ? N2 C7 H7A 111.0 . . ? C6 C7 H7A 111.0 . . ? N2 C7 H7B 111.0 . . ? C6 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? O2 C8 O3 123.63(16) . . ? O2 C8 C2 124.24(16) . . ? O3 C8 C2 112.09(14) . . ? O3 C9 C10 108.25(17) . . ? O3 C9 H9A 110.0 . . ? C10 C9 H9A 110.0 . . ? O3 C9 H9B 110.0 . . ? C10 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.61(15) . . ? C12 C11 C1 120.12(14) . . ? C16 C11 C1 120.23(14) . . ? C13 C12 C11 120.57(15) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C14 C13 C12 118.24(16) . . ? C14 C13 H13A 120.9 . . ? C12 C13 H13A 120.9 . . ? C15 C14 C13 122.76(15) . . ? C15 C14 N3 118.82(15) . . ? C13 C14 N3 118.42(15) . . ? C14 C15 C16 118.39(15) . . ? C14 C15 H15A 120.8 . . ? C16 C15 H15A 120.8 . . ? C15 C16 C11 120.42(15) . . ? C15 C16 H16A 119.8 . . ? C11 C16 H16A 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C1 145.19(14) . . . . ? C4 N1 N2 C1 -46.48(18) . . . . ? C5 N1 N2 C7 26.02(17) . . . . ? C4 N1 N2 C7 -165.65(14) . . . . ? N1 N2 C1 C11 -173.76(12) . . . . ? C7 N2 C1 C11 -60.90(16) . . . . ? N1 N2 C1 C2 63.22(15) . . . . ? C7 N2 C1 C2 176.08(12) . . . . ? N2 C1 C2 C3 -48.73(17) . . . . ? C11 C1 C2 C3 -167.62(13) . . . . ? N2 C1 C2 C8 -169.84(12) . . . . ? C11 C1 C2 C8 71.28(17) . . . . ? C8 C2 C3 C4 137.72(17) . . . . ? C1 C2 C3 C4 17.5(2) . . . . ? C2 C3 C4 N1 1.5(3) . . . . ? C5 N1 C4 C3 179.63(17) . . . . ? N2 N1 C4 C3 13.0(2) . . . . ? C4 N1 C5 O1 3.1(3) . . . . ? N2 N1 C5 O1 170.23(16) . . . . ? C4 N1 C5 C6 -176.67(16) . . . . ? N2 N1 C5 C6 -9.53(19) . . . . ? O1 C5 C6 C7 169.44(18) . . . . ? N1 C5 C6 C7 -10.82(18) . . . . ? N1 N2 C7 C6 -30.65(16) . . . . ? C1 N2 C7 C6 -147.65(13) . . . . ? C5 C6 C7 N2 25.82(17) . . . . ? C9 O3 C8 O2 -4.9(3) . . . . ? C9 O3 C8 C2 172.97(15) . . . . ? C3 C2 C8 O2 -19.3(2) . . . . ? C1 C2 C8 O2 101.33(19) . . . . ? C3 C2 C8 O3 162.86(14) . . . . ? C1 C2 C8 O3 -76.47(17) . . . . ? C8 O3 C9 C10 -178.58(18) . . . . ? N2 C1 C11 C12 119.11(16) . . . . ? C2 C1 C11 C12 -121.60(17) . . . . ? N2 C1 C11 C16 -58.65(19) . . . . ? C2 C1 C11 C16 60.6(2) . . . . ? C16 C11 C12 C13 0.9(3) . . . . ? C1 C11 C12 C13 -176.85(15) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -1.5(3) . . . . ? C12 C13 C14 N3 177.26(15) . . . . ? O4 N3 C14 C15 178.63(16) . . . . ? O5 N3 C14 C15 -0.7(2) . . . . ? O4 N3 C14 C13 -0.2(2) . . . . ? O5 N3 C14 C13 -179.48(16) . . . . ? C13 C14 C15 C16 1.5(3) . . . . ? N3 C14 C15 C16 -177.26(15) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? C1 C11 C16 C15 176.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.249 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.043