data_bd82 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 N O5' _symmetry_space_group_name_Hall P2ac2ab _chemical_formula_sum 'C16 H11 N O5' _chemical_formula_weight 297.26 _chemical_absolute_configuration ad 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 6.0151(12) _cell_length_b 10.963(2) _cell_length_c 20.032(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1321.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10958 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 26.37 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9920 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details 'Bruker SHELXTL' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker Kappa Apex2 CCD' _diffrn_measurement_method 'phi 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 10958 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1592 _reflns_number_gt 1282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _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^)+(0.0496P)^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 mixed _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_number_reflns 1592 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 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 0.5683(3) -0.25171(16) 0.03110(9) 0.0199(5) Uani 1 1 d . . . O2 O 0.8569(4) -0.62059(18) -0.02368(11) 0.0295(5) Uani 1 1 d . . . O3 O 0.5747(4) -0.52763(17) 0.13706(10) 0.0207(5) Uani 1 1 d . . . O4 O 0.1938(3) -0.26988(17) 0.14423(10) 0.0206(5) Uani 1 1 d . . . O5 O 0.0873(4) 0.03447(18) 0.20549(10) 0.0248(5) Uani 1 1 d . . . N1 N 0.7454(5) -0.4245(2) -0.00273(12) 0.0203(6) Uani 1 1 d . . . C1 C 0.5709(5) -0.3614(2) 0.02425(13) 0.0158(6) Uani 1 1 d . . . H1 H 0.852(7) -0.381(3) -0.0197(19) 0.043(11) Uiso 1 1 d . . . C2 C 0.7203(6) -0.5490(3) -0.00302(13) 0.0210(7) Uani 1 1 d . . . C3 C 0.3938(6) -0.4525(2) 0.04435(14) 0.0185(6) Uani 1 1 d . . . H3 H 0.254(6) -0.431(2) 0.0253(14) 0.014(7) Uiso 1 1 d . . . C4 C 0.4942(5) -0.5773(2) 0.02750(15) 0.0204(6) Uani 1 1 d . . . H4 H 0.411(6) -0.631(3) -0.0041(15) 0.026(9) Uiso 1 1 d . . . C5 C 0.3765(5) -0.4606(2) 0.12274(14) 0.0184(6) Uani 1 1 d . . . C6 C 0.5168(6) -0.6347(3) 0.09832(15) 0.0228(7) Uani 1 1 d . . . H6 H 0.631(6) -0.702(3) 0.1030(15) 0.027(9) Uiso 1 1 d . . . C7 C 0.1945(6) -0.5543(3) 0.13659(16) 0.0247(7) Uani 1 1 d . . . H7 H 0.051(7) -0.535(3) 0.1481(18) 0.040(11) Uiso 1 1 d . . . C8 C 0.2826(7) -0.6610(3) 0.12202(15) 0.0276(8) Uani 1 1 d . . . H8 H 0.220(6) -0.738(3) 0.1208(13) 0.018(8) Uiso 1 1 d . . . C9 C 0.3727(5) -0.3434(3) 0.15912(14) 0.0186(6) Uani 1 1 d . . . C10 C 0.5101(6) -0.2886(3) 0.20282(15) 0.0209(7) Uani 1 1 d . . . H10 H 0.634(7) -0.326(3) 0.2209(17) 0.034(10) Uiso 1 1 d . . . C11 C 0.4141(6) -0.1719(3) 0.21658(14) 0.0221(7) Uani 1 1 d . . . H11 H 0.472(5) -0.114(2) 0.2462(14) 0.010(7) Uiso 1 1 d . . . C12 C 0.2268(5) -0.1644(3) 0.18029(13) 0.0181(6) Uani 1 1 d . . . C13 C 0.0573(5) -0.0725(2) 0.17175(14) 0.0199(6) Uani 1 1 d . . . C14 C -0.1341(5) -0.0688(3) 0.13575(15) 0.0227(7) Uani 1 1 d . . . H14 H -0.179(6) -0.133(3) 0.1102(15) 0.025(9) Uiso 1 1 d . . . C15 C -0.2300(6) 0.0473(3) 0.14826(17) 0.0283(7) Uani 1 1 d . . . H15 H -0.352(7) 0.080(3) 0.1299(17) 0.029(10) Uiso 1 1 d . . . C16 C -0.0934(6) 0.1064(3) 0.19011(16) 0.0272(7) Uani 1 1 d . . . H16 H -0.098(6) 0.181(3) 0.2125(16) 0.026(9) 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 0.0183(12) 0.0171(10) 0.0244(11) 0.0016(8) -0.0032(9) 0.0006(8) O2 0.0273(13) 0.0242(11) 0.0370(13) -0.0076(10) 0.0087(11) 0.0032(10) O3 0.0221(12) 0.0204(10) 0.0194(10) 0.0016(8) -0.0015(9) 0.0039(9) O4 0.0210(12) 0.0195(10) 0.0212(10) -0.0048(8) 0.0003(9) 0.0018(9) O5 0.0231(13) 0.0233(11) 0.0281(12) -0.0059(9) 0.0009(10) 0.0013(10) N1 0.0181(15) 0.0202(12) 0.0226(13) 0.0000(10) 0.0039(12) -0.0013(12) C1 0.0132(15) 0.0211(14) 0.0132(13) 0.0007(11) -0.0033(12) 0.0000(12) C2 0.0240(18) 0.0216(14) 0.0175(15) -0.0010(11) 0.0004(13) -0.0012(14) C3 0.0171(16) 0.0203(14) 0.0181(14) -0.0020(11) -0.0022(13) 0.0000(13) C4 0.0196(16) 0.0205(14) 0.0211(15) -0.0025(12) 0.0017(13) -0.0049(13) C5 0.0174(17) 0.0199(14) 0.0180(14) 0.0010(11) 0.0012(12) 0.0021(13) C6 0.0268(18) 0.0185(15) 0.0231(16) 0.0024(12) 0.0030(14) -0.0008(14) C7 0.026(2) 0.0265(17) 0.0220(16) -0.0001(13) 0.0060(14) -0.0053(14) C8 0.038(2) 0.0219(15) 0.0227(16) 0.0013(12) 0.0080(15) -0.0077(15) C9 0.0164(16) 0.0190(14) 0.0203(15) 0.0012(10) 0.0014(12) -0.0006(12) C10 0.0199(17) 0.0252(15) 0.0176(15) -0.0013(12) 0.0009(14) -0.0017(14) C11 0.0243(18) 0.0258(15) 0.0162(15) -0.0059(12) 0.0006(14) -0.0054(14) C12 0.0192(17) 0.0209(13) 0.0143(14) -0.0022(11) 0.0036(12) -0.0038(13) C13 0.0205(17) 0.0221(15) 0.0173(14) -0.0015(11) 0.0052(12) -0.0024(13) C14 0.0220(18) 0.0218(16) 0.0242(16) -0.0015(13) 0.0023(14) -0.0027(14) C15 0.0253(19) 0.0281(17) 0.0316(18) 0.0044(14) 0.0026(15) 0.0007(16) C16 0.026(2) 0.0213(16) 0.0342(18) -0.0031(13) 0.0069(16) 0.0032(14) _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 1.211(3) . ? O2 C2 1.209(4) . ? O3 C5 1.429(4) . ? O3 C6 1.449(3) . ? O4 C12 1.378(3) . ? O4 C9 1.377(3) . ? O5 C13 1.366(3) . ? O5 C16 1.377(4) . ? N1 C1 1.368(4) . ? N1 C2 1.373(4) . ? N1 H1 0.87(4) . ? C1 C3 1.514(4) . ? C2 C4 1.523(4) . ? C3 C4 1.534(4) . ? C3 C5 1.576(4) . ? C3 H3 0.95(3) . ? C4 C6 1.558(4) . ? C4 H4 1.00(3) . ? C5 C9 1.478(4) . ? C5 C7 1.527(4) . ? C6 C8 1.514(5) . ? C6 H6 1.01(3) . ? C7 C8 1.316(5) . ? C7 H7 0.92(4) . ? C8 H8 0.93(3) . ? C9 C10 1.346(4) . ? C10 C11 1.431(4) . ? C10 H10 0.93(4) . ? C11 C12 1.343(5) . ? C11 H11 0.94(3) . ? C12 C13 1.444(4) . ? C13 C14 1.359(4) . ? C14 C15 1.420(4) . ? C14 H14 0.91(3) . ? C15 C16 1.341(5) . ? C15 H15 0.90(4) . ? C16 H16 0.94(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 C5 O3 C6 96.2(2) . . ? C12 O4 C9 105.4(2) . . ? C13 O5 C16 106.1(2) . . ? C1 N1 C2 114.8(3) . . ? C1 N1 H1 116(2) . . ? C2 N1 H1 129(2) . . ? O1 C1 N1 123.8(3) . . ? O1 C1 C3 128.0(3) . . ? N1 C1 C3 108.1(2) . . ? O2 C2 N1 124.9(3) . . ? O2 C2 C4 127.7(3) . . ? N1 C2 C4 107.4(3) . . ? C1 C3 C4 104.7(2) . . ? C1 C3 C5 110.4(2) . . ? C4 C3 C5 101.2(2) . . ? C1 C3 H3 110.4(17) . . ? C4 C3 H3 118.9(16) . . ? C5 C3 H3 110.8(18) . . ? C2 C4 C3 104.9(2) . . ? C2 C4 C6 111.7(3) . . ? C3 C4 C6 101.2(2) . . ? C2 C4 H4 108(2) . . ? C3 C4 H4 118.1(19) . . ? C6 C4 H4 112.4(17) . . ? O3 C5 C9 111.2(2) . . ? O3 C5 C7 102.4(2) . . ? C9 C5 C7 119.0(3) . . ? O3 C5 C3 100.0(2) . . ? C9 C5 C3 116.3(2) . . ? C7 C5 C3 105.5(2) . . ? O3 C6 C8 102.1(2) . . ? O3 C6 C4 100.5(2) . . ? C8 C6 C4 106.3(3) . . ? O3 C6 H6 112.0(18) . . ? C8 C6 H6 117.8(19) . . ? C4 C6 H6 115.9(18) . . ? C8 C7 C5 105.6(3) . . ? C8 C7 H7 130(2) . . ? C5 C7 H7 124(2) . . ? C7 C8 C6 105.9(3) . . ? C7 C8 H8 131(2) . . ? C6 C8 H8 123(2) . . ? C10 C9 O4 111.1(3) . . ? C10 C9 C5 134.4(3) . . ? O4 C9 C5 114.5(2) . . ? C9 C10 C11 106.1(3) . . ? C9 C10 H10 123(2) . . ? C11 C10 H10 131(2) . . ? C12 C11 C10 106.8(3) . . ? C12 C11 H11 127.8(18) . . ? C10 C11 H11 125.4(18) . . ? C11 C12 O4 110.7(3) . . ? C11 C12 C13 134.4(3) . . ? O4 C12 C13 114.9(2) . . ? C14 C13 O5 110.4(3) . . ? C14 C13 C12 133.0(3) . . ? O5 C13 C12 116.6(3) . . ? C13 C14 C15 106.1(3) . . ? C13 C14 H14 122(2) . . ? C15 C14 H14 132(2) . . ? C16 C15 C14 107.1(3) . . ? C16 C15 H15 125(2) . . ? C14 C15 H15 128(2) . . ? C15 C16 O5 110.3(3) . . ? C15 C16 H16 135(2) . . ? O5 C16 H16 115(2) . . ? 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 C2 N1 C1 O1 176.8(3) . . . . ? C2 N1 C1 C3 -1.8(3) . . . . ? C1 N1 C2 O2 -178.8(3) . . . . ? C1 N1 C2 C4 0.7(3) . . . . ? O1 C1 C3 C4 -176.5(3) . . . . ? N1 C1 C3 C4 2.0(3) . . . . ? O1 C1 C3 C5 -68.4(4) . . . . ? N1 C1 C3 C5 110.2(3) . . . . ? O2 C2 C4 C3 -179.9(3) . . . . ? N1 C2 C4 C3 0.6(3) . . . . ? O2 C2 C4 C6 71.3(4) . . . . ? N1 C2 C4 C6 -108.2(3) . . . . ? C1 C3 C4 C2 -1.5(3) . . . . ? C5 C3 C4 C2 -116.3(3) . . . . ? C1 C3 C4 C6 114.8(2) . . . . ? C5 C3 C4 C6 0.0(3) . . . . ? C6 O3 C5 C9 176.7(2) . . . . ? C6 O3 C5 C7 48.5(2) . . . . ? C6 O3 C5 C3 -59.9(2) . . . . ? C1 C3 C5 O3 -73.9(3) . . . . ? C4 C3 C5 O3 36.5(3) . . . . ? C1 C3 C5 C9 45.8(4) . . . . ? C4 C3 C5 C9 156.2(3) . . . . ? C1 C3 C5 C7 -180.0(2) . . . . ? C4 C3 C5 C7 -69.5(3) . . . . ? C5 O3 C6 C8 -49.0(2) . . . . ? C5 O3 C6 C4 60.4(2) . . . . ? C2 C4 C6 O3 75.3(3) . . . . ? C3 C4 C6 O3 -35.9(3) . . . . ? C2 C4 C6 C8 -178.6(2) . . . . ? C3 C4 C6 C8 70.2(3) . . . . ? O3 C5 C7 C8 -31.1(3) . . . . ? C9 C5 C7 C8 -154.1(3) . . . . ? C3 C5 C7 C8 73.2(3) . . . . ? C5 C7 C8 C6 -0.7(3) . . . . ? O3 C6 C8 C7 31.8(3) . . . . ? C4 C6 C8 C7 -73.1(3) . . . . ? C12 O4 C9 C10 0.8(3) . . . . ? C12 O4 C9 C5 -177.2(2) . . . . ? O3 C5 C9 C10 -1.6(4) . . . . ? C7 C5 C9 C10 117.0(4) . . . . ? C3 C5 C9 C10 -115.1(4) . . . . ? O3 C5 C9 O4 175.7(2) . . . . ? C7 C5 C9 O4 -65.7(3) . . . . ? C3 C5 C9 O4 62.2(3) . . . . ? O4 C9 C10 C11 -0.4(3) . . . . ? C5 C9 C10 C11 177.0(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 O4 0.6(3) . . . . ? C10 C11 C12 C13 -179.9(3) . . . . ? C9 O4 C12 C11 -0.9(3) . . . . ? C9 O4 C12 C13 179.6(2) . . . . ? C16 O5 C13 C14 0.5(3) . . . . ? C16 O5 C13 C12 -179.7(2) . . . . ? C11 C12 C13 C14 -178.1(3) . . . . ? O4 C12 C13 C14 1.3(5) . . . . ? C11 C12 C13 O5 2.1(5) . . . . ? O4 C12 C13 O5 -178.5(2) . . . . ? O5 C13 C14 C15 -0.5(3) . . . . ? C12 C13 C14 C15 179.7(3) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 O5 0.1(4) . . . . ? C13 O5 C16 C15 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.257 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.053