data_p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3 O3' _chemical_formula_weight 271.27 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 13.632(2) _cell_length_b 6.6388(10) _cell_length_c 14.072(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.006(8) _cell_angle_gamma 90.00 _cell_volume 1268.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2652 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_T_max 0.9718 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7420 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2754 _reflns_number_gt 2181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1633P)^2^+0.7557P] 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 2754 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1643 _refine_ls_wR_factor_gt 0.1405 _refine_ls_goodness_of_fit_ref 0.665 _refine_ls_restrained_S_all 0.665 _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 0.68578(10) 0.0907(2) 0.10715(10) 0.0321(3) Uani 1 1 d . . . C2 C 0.75557(11) 0.1413(2) 0.19320(10) 0.0321(3) Uani 1 1 d . . . C3 C 0.81096(11) 0.3197(2) 0.18992(11) 0.0381(4) Uani 1 1 d . . . H3 H 0.8029 0.4068 0.1380 0.046 Uiso 1 1 calc R . . C4 C 0.87681(12) 0.3594(3) 0.26584(12) 0.0434(4) Uani 1 1 d . . . C5 C 0.9979(2) 0.4784(5) 0.36489(17) 0.0899(9) Uani 1 1 d . . . H5A H 1.0642 0.4483 0.3492 0.108 Uiso 1 1 calc R . . H5B H 1.0009 0.5934 0.4076 0.108 Uiso 1 1 calc R . . C6 C 0.88948(12) 0.2311(3) 0.34338(12) 0.0460(4) Uani 1 1 d . . . C7 C 0.83570(13) 0.0594(3) 0.34911(11) 0.0464(4) Uani 1 1 d . . . H7 H 0.8445 -0.0247 0.4020 0.056 Uiso 1 1 calc R . . C8 C 0.76625(12) 0.0138(2) 0.27198(10) 0.0382(4) Uani 1 1 d . . . C9 C 0.70496(17) -0.1743(3) 0.27733(13) 0.0544(5) Uani 1 1 d . . . H9A H 0.7451 -0.2905 0.2650 0.065 Uiso 1 1 calc R . . H9B H 0.6845 -0.1876 0.3414 0.065 Uiso 1 1 calc R . . C10 C 0.61547(16) -0.1730(3) 0.20752(13) 0.0552(5) Uani 1 1 d . . . H10A H 0.5872 -0.3072 0.2031 0.066 Uiso 1 1 calc R . . H10B H 0.5666 -0.0826 0.2300 0.066 Uiso 1 1 calc R . . C14 C 0.73066(12) 0.0563(3) 0.01237(10) 0.0395(4) Uani 1 1 d . . . H14 H 0.7914 0.1336 0.0085 0.047 Uiso 1 1 calc R . . C15 C 0.65029(13) 0.1176(3) -0.06581(11) 0.0450(4) Uani 1 1 d . . . H15A H 0.6792 0.1629 -0.1227 0.054 Uiso 1 1 calc R . . H15B H 0.6064 0.0057 -0.0825 0.054 Uiso 1 1 calc R . . C16 C 0.59574(15) 0.2882(3) -0.02143(13) 0.0527(5) Uani 1 1 d . . . H16A H 0.6259 0.4168 -0.0339 0.063 Uiso 1 1 calc R . . H16B H 0.5274 0.2914 -0.0471 0.063 Uiso 1 1 calc R . . C17 C 0.60320(11) 0.2452(2) 0.08360(12) 0.0405(4) Uani 1 1 d . . . N1 N 0.64017(11) -0.1086(2) 0.11364(10) 0.0436(4) Uani 1 1 d . . . N2 N 0.69582(14) -0.2453(2) 0.06679(11) 0.0569(5) Uani 1 1 d . . . N3 N 0.74846(14) -0.1620(3) 0.01013(11) 0.0561(4) Uani 1 1 d . . . O1 O 0.93725(11) 0.5244(3) 0.28041(10) 0.0680(5) Uani 1 1 d . . . O2 O 0.95832(11) 0.3104(3) 0.41018(10) 0.0682(5) Uani 1 1 d . . . O3 O 0.55365(11) 0.3151(2) 0.14185(11) 0.0656(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 0.0356(7) 0.0303(7) 0.0305(7) -0.0016(5) 0.0036(5) -0.0020(5) C2 0.0357(7) 0.0320(7) 0.0289(7) -0.0037(5) 0.0038(5) 0.0009(5) C3 0.0415(8) 0.0377(8) 0.0350(8) 0.0004(6) 0.0033(6) -0.0045(6) C4 0.0386(8) 0.0512(9) 0.0408(8) -0.0069(7) 0.0056(7) -0.0105(7) C5 0.0788(15) 0.133(2) 0.0546(13) 0.0007(14) -0.0119(11) -0.0565(17) C6 0.0394(8) 0.0662(11) 0.0316(7) -0.0071(7) -0.0012(6) -0.0028(8) C7 0.0567(10) 0.0519(10) 0.0300(7) 0.0023(7) -0.0001(7) 0.0039(8) C8 0.0507(9) 0.0339(8) 0.0302(7) -0.0017(6) 0.0050(6) 0.0010(6) C9 0.0878(14) 0.0380(9) 0.0370(9) 0.0053(7) 0.0027(9) -0.0122(9) C10 0.0750(12) 0.0458(10) 0.0454(10) 0.0043(7) 0.0079(9) -0.0245(9) C14 0.0410(8) 0.0474(9) 0.0301(7) -0.0024(6) 0.0034(6) 0.0026(7) C15 0.0516(9) 0.0485(9) 0.0337(8) 0.0021(7) -0.0036(7) -0.0042(7) C16 0.0578(10) 0.0474(10) 0.0495(10) 0.0026(8) -0.0135(8) 0.0075(8) C17 0.0357(7) 0.0362(8) 0.0493(9) -0.0042(7) 0.0018(6) 0.0001(6) N1 0.0595(8) 0.0338(7) 0.0370(7) -0.0021(5) 0.0013(6) -0.0096(6) N2 0.0918(12) 0.0383(8) 0.0385(8) -0.0089(6) -0.0072(8) 0.0070(8) N3 0.0782(11) 0.0537(10) 0.0357(8) -0.0092(7) 0.0007(7) 0.0209(8) O1 0.0652(9) 0.0813(11) 0.0555(8) -0.0031(7) -0.0055(7) -0.0404(8) O2 0.0567(8) 0.1026(13) 0.0426(7) -0.0050(7) -0.0105(6) -0.0244(8) O3 0.0580(8) 0.0680(10) 0.0733(10) -0.0031(7) 0.0202(7) 0.0202(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 N1 1.4680(19) . ? C1 C2 1.5111(19) . ? C1 C14 1.532(2) . ? C1 C17 1.538(2) . ? C2 C8 1.392(2) . ? C2 C3 1.407(2) . ? C3 C4 1.360(2) . ? C3 H3 0.9300 . ? C4 O1 1.375(2) . ? C4 C6 1.383(3) . ? C5 O2 1.415(3) . ? C5 O1 1.420(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.361(3) . ? C6 O2 1.374(2) . ? C7 C8 1.410(2) . ? C7 H7 0.9300 . ? C8 C9 1.508(2) . ? C9 C10 1.498(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N1 1.456(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C14 N3 1.470(2) . ? C14 C15 1.538(2) . ? C14 H14 0.9800 . ? C15 C16 1.519(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.500(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.200(2) . ? N1 N2 1.386(2) . ? N2 N3 1.248(2) . ? 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 N1 C1 C2 113.02(12) . . ? N1 C1 C14 97.06(11) . . ? C2 C1 C14 117.35(12) . . ? N1 C1 C17 107.98(12) . . ? C2 C1 C17 114.97(12) . . ? C14 C1 C17 104.63(12) . . ? C8 C2 C3 121.24(14) . . ? C8 C2 C1 121.17(13) . . ? C3 C2 C1 117.57(13) . . ? C4 C3 C2 117.16(15) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C3 C4 O1 128.11(17) . . ? C3 C4 C6 121.93(16) . . ? O1 C4 C6 109.94(15) . . ? O2 C5 O1 109.26(16) . . ? O2 C5 H5A 109.8 . . ? O1 C5 H5A 109.8 . . ? O2 C5 H5B 109.8 . . ? O1 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? C7 C6 O2 128.28(17) . . ? C7 C6 C4 122.11(15) . . ? O2 C6 C4 109.55(16) . . ? C6 C7 C8 117.60(16) . . ? C6 C7 H7 121.2 . . ? C8 C7 H7 121.2 . . ? C2 C8 C7 119.93(15) . . ? C2 C8 C9 121.56(14) . . ? C7 C8 C9 118.52(15) . . ? C10 C9 C8 112.68(14) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N1 C10 C9 110.92(16) . . ? N1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? N3 C14 C1 104.19(13) . . ? N3 C14 C15 110.75(14) . . ? C1 C14 C15 105.63(13) . . ? N3 C14 H14 111.9 . . ? C1 C14 H14 111.9 . . ? C15 C14 H14 111.9 . . ? C16 C15 C14 104.30(13) . . ? C16 C15 H15A 110.9 . . ? C14 C15 H15A 110.9 . . ? C16 C15 H15B 110.9 . . ? C14 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? C17 C16 C15 105.66(14) . . ? C17 C16 H16A 110.6 . . ? C15 C16 H16A 110.6 . . ? C17 C16 H16B 110.6 . . ? C15 C16 H16B 110.6 . . ? H16A C16 H16B 108.7 . . ? O3 C17 C16 127.28(16) . . ? O3 C17 C1 123.78(16) . . ? C16 C17 C1 108.94(13) . . ? N2 N1 C10 114.73(15) . . ? N2 N1 C1 107.97(13) . . ? C10 N1 C1 117.01(13) . . ? N3 N2 N1 112.48(15) . . ? N2 N3 C14 108.56(14) . . ? C4 O1 C5 104.52(17) . . ? C6 O2 C5 104.97(15) . . ? 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 N1 C1 C2 C8 -5.05(19) . . . . ? C14 C1 C2 C8 -116.77(16) . . . . ? C17 C1 C2 C8 119.55(15) . . . . ? N1 C1 C2 C3 173.55(13) . . . . ? C14 C1 C2 C3 61.83(18) . . . . ? C17 C1 C2 C3 -61.85(17) . . . . ? C8 C2 C3 C4 1.5(2) . . . . ? C1 C2 C3 C4 -177.09(14) . . . . ? C2 C3 C4 O1 -178.32(16) . . . . ? C2 C3 C4 C6 0.0(2) . . . . ? C3 C4 C6 C7 -1.2(3) . . . . ? O1 C4 C6 C7 177.45(16) . . . . ? C3 C4 C6 O2 -178.44(16) . . . . ? O1 C4 C6 O2 0.2(2) . . . . ? O2 C6 C7 C8 177.48(17) . . . . ? C4 C6 C7 C8 0.7(3) . . . . ? C3 C2 C8 C7 -1.9(2) . . . . ? C1 C2 C8 C7 176.63(14) . . . . ? C3 C2 C8 C9 178.11(15) . . . . ? C1 C2 C8 C9 -3.3(2) . . . . ? C6 C7 C8 C2 0.8(2) . . . . ? C6 C7 C8 C9 -179.26(16) . . . . ? C2 C8 C9 C10 -17.5(2) . . . . ? C7 C8 C9 C10 162.56(16) . . . . ? C8 C9 C10 N1 45.9(2) . . . . ? N1 C1 C14 N3 -28.50(15) . . . . ? C2 C1 C14 N3 92.01(16) . . . . ? C17 C1 C14 N3 -139.21(13) . . . . ? N1 C1 C14 C15 88.25(14) . . . . ? C2 C1 C14 C15 -151.23(13) . . . . ? C17 C1 C14 C15 -22.46(16) . . . . ? N3 C14 C15 C16 145.19(15) . . . . ? C1 C14 C15 C16 32.97(17) . . . . ? C14 C15 C16 C17 -30.42(18) . . . . ? C15 C16 C17 O3 -162.51(18) . . . . ? C15 C16 C17 C1 16.77(18) . . . . ? N1 C1 C17 O3 80.37(19) . . . . ? C2 C1 C17 O3 -46.8(2) . . . . ? C14 C1 C17 O3 -177.02(17) . . . . ? N1 C1 C17 C16 -98.94(15) . . . . ? C2 C1 C17 C16 133.86(14) . . . . ? C14 C1 C17 C16 3.67(17) . . . . ? C9 C10 N1 N2 70.05(19) . . . . ? C9 C10 N1 C1 -58.0(2) . . . . ? C2 C1 N1 N2 -94.83(14) . . . . ? C14 C1 N1 N2 28.93(14) . . . . ? C17 C1 N1 N2 136.85(13) . . . . ? C2 C1 N1 C10 36.4(2) . . . . ? C14 C1 N1 C10 160.15(16) . . . . ? C17 C1 N1 C10 -91.93(18) . . . . ? C10 N1 N2 N3 -152.11(15) . . . . ? C1 N1 N2 N3 -19.66(18) . . . . ? N1 N2 N3 C14 -1.0(2) . . . . ? C1 C14 N3 N2 20.01(19) . . . . ? C15 C14 N3 N2 -93.13(16) . . . . ? C3 C4 O1 C5 -173.7(2) . . . . ? C6 C4 O1 C5 7.8(2) . . . . ? O2 C5 O1 C4 -13.0(3) . . . . ? C7 C6 O2 C5 174.8(2) . . . . ? C4 C6 O2 C5 -8.1(2) . . . . ? O1 C5 O2 C6 13.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.258 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.036