data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name B.R.Dhevalapally M.Kishor Y.V.Reddy C.Venkaiah _publ_contact_author_name 'B. Ramachary Dhevalapally' _publ_contact_author_email RAMSC@UOHYD.ERNET.IN data_dbr59 _database_code_depnum_ccdc_archive 'CCDC 713797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.10 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 12.482(9) _cell_length_b 13.018(10) _cell_length_c 8.140(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.639(12) _cell_angle_gamma 90.00 _cell_volume 1260.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4594 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.89 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 550 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _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 12642 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.06 _reflns_number_total 2481 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0621P)^2^+0.1499P] 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 2481 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _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 0.75777(12) 0.96508(12) 0.3107(2) 0.0416(4) Uani 1 1 d . . . C2 C 0.64907(13) 0.98252(12) 0.1916(2) 0.0412(4) Uani 1 1 d . . . C3 C 0.63293(14) 0.79953(12) 0.1598(2) 0.0473(4) Uani 1 1 d . . . C4 C 0.79172(13) 0.86481(13) 0.3418(2) 0.0467(4) Uani 1 1 d . . . C5 C 0.82661(13) 1.05564(12) 0.4027(2) 0.0452(4) Uani 1 1 d . . . H5A H 0.8079 1.1158 0.3293 0.054 Uiso 1 1 calc R . . H5B H 0.9058 1.0411 0.4234 0.054 Uiso 1 1 calc R . . C6 C 0.80564(12) 1.07846(11) 0.57329(19) 0.0409(4) Uani 1 1 d . . . C7 C 0.71461(15) 1.13832(12) 0.5783(2) 0.0511(4) Uani 1 1 d . . . H7 H 0.6684 1.1669 0.4768 0.061 Uiso 1 1 calc R . . C8 C 0.69141(17) 1.15626(15) 0.7313(3) 0.0620(5) Uani 1 1 d . . . H8 H 0.6303 1.1969 0.7322 0.074 Uiso 1 1 calc R . . C9 C 0.75892(17) 1.11393(15) 0.8827(2) 0.0631(5) Uani 1 1 d . . . H9 H 0.7436 1.1260 0.9859 0.076 Uiso 1 1 calc R . . C10 C 0.84869(18) 1.05392(15) 0.8802(2) 0.0656(5) Uani 1 1 d . . . H10 H 0.8938 1.0247 0.9819 0.079 Uiso 1 1 calc R . . C11 C 0.87258(15) 1.03666(14) 0.7273(2) 0.0564(5) Uani 1 1 d . . . H11 H 0.9343 0.9965 0.7276 0.068 Uiso 1 1 calc R . . C12 C 0.93483(18) 0.74354(16) 0.4867(3) 0.0798(7) Uani 1 1 d . . . H12A H 0.8836 0.7043 0.5289 0.120 Uiso 1 1 calc R . . H12B H 1.0078 0.7434 0.5711 0.120 Uiso 1 1 calc R . . H12C H 0.9399 0.7136 0.3815 0.120 Uiso 1 1 calc R . . C13 C 0.59885(16) 0.62069(14) 0.1230(3) 0.0694(6) Uani 1 1 d . . . H13A H 0.6729 0.6108 0.1131 0.104 Uiso 1 1 calc R . . H13B H 0.5473 0.5747 0.0459 0.104 Uiso 1 1 calc R . . H13C H 0.5998 0.6069 0.2393 0.104 Uiso 1 1 calc R . . N1 N 0.73100(11) 0.78045(10) 0.26959(18) 0.0505(4) Uani 1 1 d . . . N2 N 0.59054(11) 0.89446(10) 0.11715(18) 0.0474(4) Uani 1 1 d . . . H2 H 0.5249(19) 0.9025(16) 0.033(3) 0.079(6) Uiso 1 1 d . . . O1 O 0.60383(9) 1.06832(8) 0.15122(15) 0.0512(3) Uani 1 1 d . . . O2 O 0.56359(10) 0.72569(9) 0.07881(17) 0.0631(4) Uani 1 1 d . . . O3 O 0.89470(10) 0.84771(9) 0.45461(18) 0.0657(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 0.0367(8) 0.0470(9) 0.0398(9) -0.0054(7) 0.0097(7) -0.0016(7) C2 0.0381(8) 0.0430(9) 0.0403(9) -0.0052(7) 0.0087(7) 0.0004(7) C3 0.0425(9) 0.0445(9) 0.0522(10) -0.0086(8) 0.0101(8) -0.0019(7) C4 0.0364(8) 0.0526(10) 0.0469(10) -0.0060(8) 0.0063(7) 0.0024(7) C5 0.0367(8) 0.0489(9) 0.0461(9) -0.0019(7) 0.0068(7) -0.0047(7) C6 0.0383(8) 0.0368(8) 0.0420(9) -0.0032(7) 0.0040(7) -0.0089(7) C7 0.0549(10) 0.0455(9) 0.0472(10) 0.0009(7) 0.0071(8) 0.0039(8) C8 0.0633(12) 0.0623(12) 0.0608(12) -0.0085(9) 0.0195(10) 0.0085(9) C9 0.0763(13) 0.0645(12) 0.0497(11) -0.0079(9) 0.0210(10) -0.0102(11) C10 0.0749(13) 0.0679(13) 0.0434(11) 0.0045(9) 0.0022(9) 0.0008(10) C11 0.0489(10) 0.0608(11) 0.0502(11) -0.0012(8) 0.0010(8) 0.0062(8) C12 0.0595(12) 0.0648(13) 0.0960(17) 0.0041(12) -0.0049(11) 0.0195(10) C13 0.0661(13) 0.0430(10) 0.0937(16) -0.0110(10) 0.0163(11) -0.0017(9) N1 0.0430(8) 0.0465(8) 0.0561(9) -0.0063(6) 0.0064(7) 0.0033(6) N2 0.0385(8) 0.0452(8) 0.0498(9) -0.0069(6) 0.0004(6) 0.0013(6) O1 0.0456(6) 0.0450(7) 0.0532(7) -0.0040(5) 0.0005(5) 0.0021(5) O2 0.0511(7) 0.0431(7) 0.0814(9) -0.0121(6) -0.0004(6) -0.0032(5) O3 0.0438(7) 0.0575(8) 0.0782(9) -0.0049(6) -0.0078(6) 0.0090(6) _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 C2 1.2497(19) . ? N1 C3 1.302(2) . ? N1 C4 1.362(2) . ? O3 C4 1.353(2) . ? O3 C12 1.442(2) . ? N2 C3 1.348(2) . ? N2 C2 1.395(2) . ? C1 C4 1.372(2) . ? C1 C2 1.427(2) . ? C1 C5 1.516(2) . ? O2 C3 1.327(2) . ? O2 C13 1.448(2) . ? C6 C7 1.389(2) . ? C6 C11 1.390(2) . ? C6 C5 1.518(2) . ? C7 C8 1.381(3) . ? C11 C10 1.383(3) . ? C10 C9 1.371(3) . ? C8 C9 1.380(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 C3 N1 C4 115.26(14) . . ? C4 O3 C12 118.98(14) . . ? C3 N2 C2 121.90(15) . . ? C4 C1 C2 116.98(14) . . ? C4 C1 C5 123.46(15) . . ? C2 C1 C5 119.47(14) . . ? O1 C2 N2 118.99(14) . . ? O1 C2 C1 125.58(14) . . ? N2 C2 C1 115.43(14) . . ? C3 O2 C13 117.19(15) . . ? C7 C6 C11 117.83(16) . . ? C7 C6 C5 120.42(14) . . ? C11 C6 C5 121.68(16) . . ? O3 C4 N1 116.75(15) . . ? O3 C4 C1 117.31(14) . . ? N1 C4 C1 125.94(15) . . ? C1 C5 C6 112.02(13) . . ? C8 C7 C6 121.24(16) . . ? N1 C3 O2 122.59(15) . . ? N1 C3 N2 124.45(15) . . ? O2 C3 N2 112.96(15) . . ? C10 C11 C6 120.89(18) . . ? C9 C10 C11 120.39(18) . . ? C9 C8 C7 119.98(19) . . ? C10 C9 C8 119.66(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.192 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.042