data_2064 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 N2 O5' _chemical_formula_weight 424.40 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7844(6) _cell_length_b 12.8542(5) _cell_length_c 11.9648(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.052(5) _cell_angle_gamma 90.00 _cell_volume 1964.95(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16750 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4282 _reflns_number_gt 2734 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0251P)^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_number_reflns 4282 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0657 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.66207(11) 0.04104(10) 0.77698(12) 0.0214(3) Uani 1 1 d . . . C2 C 0.56708(11) 0.09851(9) 0.80240(12) 0.0203(3) Uani 1 1 d . . . C3 C 0.52983(12) 0.10195(10) 0.91072(12) 0.0249(3) Uani 1 1 d . . . H3 H 0.5694 0.0709 0.9706 0.030 Uiso 1 1 calc R . . C4 C 0.43640(12) 0.14988(10) 0.93132(12) 0.0280(4) Uani 1 1 d . . . H4 H 0.4119 0.1530 1.0053 0.034 Uiso 1 1 calc R . . C5 C 0.37798(12) 0.19384(10) 0.84305(12) 0.0277(4) Uani 1 1 d . . . H5 H 0.3126 0.2254 0.8572 0.033 Uiso 1 1 calc R . . C6 C 0.41295(11) 0.19255(10) 0.73626(12) 0.0240(3) Uani 1 1 d . . . H6 H 0.3729 0.2232 0.6765 0.029 Uiso 1 1 calc R . . C7 C 0.50839(11) 0.14537(10) 0.71757(12) 0.0205(3) Uani 1 1 d . . . C8 C 0.63426(11) 0.10415(10) 0.58494(12) 0.0202(3) Uani 1 1 d . . . C9 C 0.68984(10) 0.04626(9) 0.66082(11) 0.0184(3) Uani 1 1 d . . . C10 C 0.65767(11) 0.12236(9) 0.46671(12) 0.0215(3) Uani 1 1 d . . . C11 C 0.58000(12) 0.10882(9) 0.38487(12) 0.0257(4) Uani 1 1 d . . . H11 H 0.5117 0.0886 0.4047 0.031 Uiso 1 1 calc R . . C12 C 0.60206(14) 0.12480(10) 0.27400(13) 0.0326(4) Uani 1 1 d . . . H12 H 0.5493 0.1129 0.2175 0.039 Uiso 1 1 calc R . . C13 C 0.69963(14) 0.15771(11) 0.24483(13) 0.0373(4) Uani 1 1 d . . . H13 H 0.7139 0.1695 0.1685 0.045 Uiso 1 1 calc R . . C14 C 0.77685(13) 0.17354(11) 0.32647(13) 0.0382(4) Uani 1 1 d . . . H14 H 0.8441 0.1970 0.3064 0.046 Uiso 1 1 calc R . . C15 C 0.75654(12) 0.15533(11) 0.43778(13) 0.0307(4) Uani 1 1 d . . . H15 H 0.8100 0.1653 0.4940 0.037 Uiso 1 1 calc R . . C16 C 0.76264(12) -0.08729(10) 0.53767(12) 0.0233(3) Uani 1 1 d . . . C17 C 0.86034(12) -0.13767(11) 0.49830(13) 0.0363(4) Uani 1 1 d . . . H17A H 0.8841 -0.1904 0.5526 0.054 Uiso 1 1 calc R . . H17B H 0.9150 -0.0849 0.4910 0.054 Uiso 1 1 calc R . . H17C H 0.8459 -0.1707 0.4255 0.054 Uiso 1 1 calc R . . C18 C 0.93422(11) 0.06564(10) 0.70503(12) 0.0222(3) Uani 1 1 d . . . C19 C 1.01099(10) 0.03093(10) 0.79206(11) 0.0201(3) Uani 1 1 d . . . C20 C 1.09808(11) 0.08092(10) 0.83594(12) 0.0260(4) Uani 1 1 d . . . H20 H 1.1181 0.1475 0.8096 0.031 Uiso 1 1 calc R . . C21 C 1.15552(11) 0.03070(11) 0.92006(12) 0.0277(4) Uani 1 1 d . . . H21 H 1.2156 0.0637 0.9528 0.033 Uiso 1 1 calc R . . C22 C 1.12685(11) -0.06688(10) 0.95727(12) 0.0258(4) Uani 1 1 d . . . H22 H 1.1671 -0.0993 1.0158 0.031 Uiso 1 1 calc R . . C23 C 1.04060(11) -0.11796(10) 0.91069(12) 0.0223(3) Uani 1 1 d . . . H23 H 1.0216 -0.1855 0.9349 0.027 Uiso 1 1 calc R . . C24 C 0.98356(11) -0.06718(9) 0.82816(12) 0.0199(3) Uani 1 1 d . . . C25 C 0.88893(11) -0.10120(10) 0.76390(11) 0.0202(3) Uani 1 1 d . . . N1 N 0.77529(9) -0.01425(8) 0.62295(9) 0.0200(3) Uani 1 1 d . . . N2 N 0.86572(8) -0.01805(8) 0.68974(9) 0.0206(3) Uani 1 1 d . . . O1 O 0.71292(8) -0.00825(7) 0.84835(8) 0.0315(3) Uani 1 1 d . . . O2 O 0.54323(7) 0.15049(7) 0.61058(8) 0.0230(2) Uani 1 1 d . . . O3 O 0.67697(8) -0.10433(7) 0.49646(8) 0.0300(3) Uani 1 1 d . . . O4 O 0.84140(8) -0.18185(7) 0.76498(8) 0.0268(2) Uani 1 1 d . . . O5 O 0.92668(8) 0.14726(7) 0.65592(8) 0.0312(3) 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 0.0191(8) 0.0208(7) 0.0241(8) -0.0005(6) -0.0009(7) -0.0023(6) C2 0.0175(8) 0.0204(7) 0.0231(8) -0.0018(6) 0.0021(7) -0.0022(6) C3 0.0252(9) 0.0288(8) 0.0205(8) -0.0008(6) -0.0003(7) -0.0014(7) C4 0.0276(9) 0.0323(8) 0.0246(9) -0.0057(7) 0.0073(8) -0.0005(7) C5 0.0187(9) 0.0292(8) 0.0355(10) -0.0064(7) 0.0053(8) 0.0010(7) C6 0.0188(8) 0.0247(7) 0.0283(9) -0.0019(6) -0.0006(7) 0.0010(6) C7 0.0190(8) 0.0213(7) 0.0214(8) -0.0026(6) 0.0036(7) -0.0022(6) C8 0.0151(8) 0.0217(7) 0.0241(8) -0.0019(6) 0.0026(7) -0.0007(6) C9 0.0146(8) 0.0191(7) 0.0216(8) -0.0012(6) 0.0001(6) 0.0000(6) C10 0.0222(8) 0.0206(7) 0.0219(8) 0.0024(6) 0.0040(7) 0.0054(6) C11 0.0280(9) 0.0232(7) 0.0260(9) 0.0026(6) 0.0015(7) 0.0023(7) C12 0.0454(11) 0.0283(8) 0.0239(9) 0.0008(7) -0.0012(8) 0.0094(8) C13 0.0496(12) 0.0388(9) 0.0245(10) 0.0093(7) 0.0145(9) 0.0189(9) C14 0.0313(10) 0.0444(9) 0.0401(11) 0.0142(8) 0.0160(9) 0.0090(8) C15 0.0251(9) 0.0350(8) 0.0321(10) 0.0085(7) 0.0040(8) 0.0050(7) C16 0.0268(9) 0.0221(7) 0.0213(8) 0.0025(6) 0.0032(7) 0.0008(6) C17 0.0364(11) 0.0383(9) 0.0346(10) -0.0060(7) 0.0082(8) 0.0095(8) C18 0.0186(8) 0.0215(7) 0.0268(8) -0.0011(6) 0.0059(7) 0.0006(6) C19 0.0174(8) 0.0208(7) 0.0225(8) -0.0012(6) 0.0050(7) 0.0007(6) C20 0.0226(9) 0.0251(7) 0.0306(9) 0.0009(7) 0.0034(7) -0.0035(7) C21 0.0198(8) 0.0336(8) 0.0296(9) -0.0043(7) -0.0016(7) -0.0033(7) C22 0.0237(9) 0.0292(8) 0.0244(9) -0.0023(6) -0.0010(7) 0.0067(7) C23 0.0217(8) 0.0209(7) 0.0244(8) -0.0027(6) 0.0031(7) 0.0025(6) C24 0.0164(8) 0.0199(7) 0.0235(8) -0.0036(6) 0.0034(7) 0.0022(6) C25 0.0183(8) 0.0195(7) 0.0232(8) -0.0014(6) 0.0048(7) 0.0034(6) N1 0.0152(6) 0.0229(6) 0.0219(7) -0.0018(5) -0.0005(5) 0.0014(5) N2 0.0148(7) 0.0198(6) 0.0269(7) 0.0022(5) -0.0022(6) -0.0001(5) O1 0.0297(6) 0.0412(6) 0.0236(6) 0.0047(5) -0.0013(5) 0.0108(5) O2 0.0193(6) 0.0285(5) 0.0213(6) 0.0014(4) 0.0017(5) 0.0044(4) O3 0.0283(7) 0.0313(5) 0.0300(6) -0.0054(5) -0.0040(5) -0.0033(5) O4 0.0259(6) 0.0186(5) 0.0356(6) -0.0001(4) -0.0020(5) -0.0034(4) O5 0.0290(6) 0.0246(5) 0.0397(7) 0.0092(5) -0.0018(5) -0.0039(5) _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 1.2302(15) . ? C1 C9 1.4483(19) . ? C1 C2 1.4627(18) . ? C2 C7 1.3789(18) . ? C2 C3 1.3973(19) . ? C3 C4 1.3741(19) . ? C4 C5 1.3913(19) . ? C5 C6 1.3688(19) . ? C6 C7 1.3879(18) . ? C7 O2 1.3720(16) . ? C8 O2 1.3522(15) . ? C8 C9 1.3553(18) . ? C8 C10 1.4751(19) . ? C9 N1 1.4279(16) . ? C10 C11 1.3804(18) . ? C10 C15 1.3887(19) . ? C11 C12 1.3813(19) . ? C12 C13 1.374(2) . ? C13 C14 1.379(2) . ? C14 C15 1.386(2) . ? C16 O3 1.2049(16) . ? C16 N1 1.3918(17) . ? C16 C17 1.4978(19) . ? C18 O5 1.2046(15) . ? C18 N2 1.3951(16) . ? C18 C19 1.4743(19) . ? C19 C20 1.3734(18) . ? C19 C24 1.3824(17) . ? C20 C21 1.3843(19) . ? C21 C22 1.3847(18) . ? C22 C23 1.3832(18) . ? C23 C24 1.3716(18) . ? C24 C25 1.4763(19) . ? C25 O4 1.2020(14) . ? C25 N2 1.4137(16) . ? N1 N2 1.3826(14) . ? 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 C9 123.25(13) . . ? O1 C1 C2 122.53(13) . . ? C9 C1 C2 114.21(12) . . ? C7 C2 C3 118.32(13) . . ? C7 C2 C1 120.10(13) . . ? C3 C2 C1 121.46(13) . . ? C4 C3 C2 120.52(13) . . ? C3 C4 C5 119.50(14) . . ? C6 C5 C4 121.28(14) . . ? C5 C6 C7 118.30(13) . . ? O2 C7 C2 121.43(12) . . ? O2 C7 C6 116.49(12) . . ? C2 C7 C6 122.05(13) . . ? O2 C8 C9 121.65(13) . . ? O2 C8 C10 110.70(11) . . ? C9 C8 C10 127.59(13) . . ? C8 C9 N1 118.38(12) . . ? C8 C9 C1 121.84(13) . . ? N1 C9 C1 119.73(11) . . ? C11 C10 C15 119.98(13) . . ? C11 C10 C8 119.66(13) . . ? C15 C10 C8 120.35(13) . . ? C10 C11 C12 119.75(15) . . ? C13 C12 C11 120.54(15) . . ? C12 C13 C14 119.93(15) . . ? C13 C14 C15 120.12(16) . . ? C14 C15 C10 119.64(15) . . ? O3 C16 N1 120.17(13) . . ? O3 C16 C17 123.28(13) . . ? N1 C16 C17 116.48(13) . . ? O5 C18 N2 124.67(13) . . ? O5 C18 C19 130.37(13) . . ? N2 C18 C19 104.95(11) . . ? C20 C19 C24 121.24(13) . . ? C20 C19 C18 129.68(12) . . ? C24 C19 C18 109.08(12) . . ? C19 C20 C21 117.48(12) . . ? C20 C21 C22 121.10(13) . . ? C23 C22 C21 121.12(13) . . ? C24 C23 C22 117.37(13) . . ? C23 C24 C19 121.66(13) . . ? C23 C24 C25 129.69(12) . . ? C19 C24 C25 108.65(12) . . ? O4 C25 N2 124.34(13) . . ? O4 C25 C24 130.92(12) . . ? N2 C25 C24 104.63(11) . . ? N2 N1 C16 118.21(11) . . ? N2 N1 C9 117.98(10) . . ? C16 N1 C9 122.01(11) . . ? N1 N2 C18 123.81(10) . . ? N1 N2 C25 122.81(11) . . ? C18 N2 C25 112.59(11) . . ? C8 O2 C7 120.08(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.183 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.039