data_15sepd _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N2 O2' _chemical_formula_sum 'C11 H14 N2 O2' _chemical_formula_weight 206.24 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6419(5) _cell_length_b 9.2073(4) _cell_length_c 22.7567(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2229.77(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1589 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.1 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 16507 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.07 _reflns_number_total 1979 _reflns_number_gt 1589 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT PLUS' _computing_structure_solution 'SIR97(Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0511P)^2^+0.7672P] 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 1979 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 O2 O 0.36029(10) 0.27203(12) 0.10745(5) 0.0243(3) Uani 1 1 d . . . O1 O 0.38499(10) 0.23527(12) 0.20459(5) 0.0242(3) Uani 1 1 d . . . N2 N 0.54752(15) 0.00646(17) 0.23569(6) 0.0250(4) Uani 1 1 d . . . C5 C 0.49966(14) 0.09291(17) 0.13701(7) 0.0179(4) Uani 1 1 d . . . C6 C 0.41184(15) 0.20355(17) 0.15368(7) 0.0187(4) Uani 1 1 d . . . C1 C 0.55800(14) 0.00681(16) 0.17727(7) 0.0183(4) Uani 1 1 d . . . C3 C 0.66522(15) -0.02481(18) 0.08595(7) 0.0200(4) Uani 1 1 d . . . N1 N 0.52067(14) -0.34421(16) 0.13274(7) 0.0302(4) Uani 1 1 d . . . C2 C 0.64568(15) -0.10091(17) 0.14676(7) 0.0189(4) Uani 1 1 d . . . C9 C 0.76941(15) -0.13020(18) 0.17901(7) 0.0243(4) Uani 1 1 d . . . H9A H 0.7527 -0.1837 0.2144 0.036 Uiso 1 1 calc R . . H9B H 0.8089 -0.0396 0.1887 0.036 Uiso 1 1 calc R . . H9C H 0.8242 -0.1857 0.1541 0.036 Uiso 1 1 calc R . . C10 C 0.57556(15) -0.23835(18) 0.13889(7) 0.0210(4) Uani 1 1 d . . . C4 C 0.54084(15) 0.05597(19) 0.07547(7) 0.0204(4) Uani 1 1 d . . . C7 C 0.27164(16) 0.38539(18) 0.12136(8) 0.0294(4) Uani 1 1 d . . . H7A H 0.2081 0.3477 0.1471 0.044 Uiso 1 1 calc R . . H7B H 0.2332 0.4199 0.0858 0.044 Uiso 1 1 calc R . . H7C H 0.3146 0.4641 0.1404 0.044 Uiso 1 1 calc R . . C11 C 0.70827(16) -0.12039(19) 0.03686(7) 0.0248(4) Uani 1 1 d . . . C12 C 0.81875(19) -0.1085(2) 0.01146(9) 0.0361(5) Uani 1 1 d . . . H3 H 0.7288(15) 0.0508(18) 0.0938(6) 0.016(4) Uiso 1 1 d . . . H4A H 0.5540(14) 0.1417(18) 0.0516(7) 0.018(4) Uiso 1 1 d . . . H4 H 0.4787(16) -0.0080(17) 0.0549(7) 0.019(4) Uiso 1 1 d . . . H11 H 0.6490(17) -0.194(2) 0.0240(7) 0.029(5) Uiso 1 1 d . . . H12A H 0.880(2) -0.037(2) 0.0264(9) 0.043(6) Uiso 1 1 d . . . H12 H 0.8427(19) -0.170(2) -0.0208(9) 0.047(6) Uiso 1 1 d . . . H2A H 0.5788(16) -0.062(2) 0.2569(8) 0.028(5) Uiso 1 1 d . . . H2 H 0.499(2) 0.071(2) 0.2513(9) 0.038(6) 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 O2 0.0225(6) 0.0236(6) 0.0267(6) 0.0004(5) -0.0033(5) 0.0069(5) O1 0.0260(6) 0.0224(6) 0.0242(6) -0.0032(5) 0.0018(5) 0.0029(5) N2 0.0309(8) 0.0242(8) 0.0200(8) 0.0029(7) 0.0024(7) 0.0085(7) C5 0.0156(8) 0.0170(8) 0.0210(8) -0.0003(6) -0.0004(6) -0.0021(7) C6 0.0161(8) 0.0165(8) 0.0235(9) 0.0004(7) -0.0017(6) -0.0043(7) C1 0.0156(8) 0.0177(8) 0.0215(9) -0.0005(7) 0.0007(6) -0.0046(7) C3 0.0184(8) 0.0203(8) 0.0213(8) 0.0014(7) 0.0006(7) -0.0018(7) N1 0.0275(8) 0.0246(8) 0.0384(9) -0.0014(7) 0.0009(7) -0.0025(7) C2 0.0178(8) 0.0181(8) 0.0207(8) -0.0001(6) 0.0015(6) -0.0013(7) C9 0.0201(9) 0.0267(9) 0.0260(9) 0.0027(7) -0.0009(7) 0.0015(7) C10 0.0194(8) 0.0222(9) 0.0215(8) 0.0009(7) 0.0022(7) 0.0054(8) C4 0.0199(8) 0.0207(9) 0.0207(9) 0.0014(7) 0.0008(7) -0.0007(7) C7 0.0259(9) 0.0251(9) 0.0371(10) 0.0003(8) -0.0045(8) 0.0087(8) C11 0.0258(9) 0.0266(10) 0.0219(9) 0.0014(7) -0.0004(7) 0.0052(8) C12 0.0373(11) 0.0412(12) 0.0299(11) 0.0018(9) 0.0081(9) 0.0119(10) _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 O2 C6 1.3435(19) . ? O2 C7 1.4421(19) . ? O1 C6 1.2286(18) . ? N2 C1 1.334(2) . ? C5 C1 1.361(2) . ? C5 C6 1.434(2) . ? C5 C4 1.506(2) . ? C1 C2 1.529(2) . ? C3 C11 1.494(2) . ? C3 C4 1.537(2) . ? C3 C2 1.565(2) . ? N1 C10 1.145(2) . ? C2 C10 1.480(2) . ? C2 C9 1.531(2) . ? C11 C12 1.315(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 C6 O2 C7 115.78(13) . . ? C1 C5 C6 122.22(14) . . ? C1 C5 C4 111.19(14) . . ? C6 C5 C4 126.59(14) . . ? O1 C6 O2 122.13(14) . . ? O1 C6 C5 124.75(14) . . ? O2 C6 C5 113.12(14) . . ? N2 C1 C5 129.33(15) . . ? N2 C1 C2 120.15(14) . . ? C5 C1 C2 110.52(14) . . ? C11 C3 C4 115.66(14) . . ? C11 C3 C2 115.99(13) . . ? C4 C3 C2 103.85(12) . . ? C10 C2 C1 107.58(12) . . ? C10 C2 C9 109.93(13) . . ? C1 C2 C9 114.92(13) . . ? C10 C2 C3 110.05(13) . . ? C1 C2 C3 101.09(12) . . ? C9 C2 C3 112.85(13) . . ? N1 C10 C2 179.59(19) . . ? C5 C4 C3 102.45(13) . . ? C12 C11 C3 123.64(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.201 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.045