data_04359n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 04359 _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O2' _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 _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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 '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 5.9338(5) _cell_length_b 8.0456(7) _cell_length_c 24.269(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1158.61(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3137 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.17 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8355 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1571 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0343P)^2^+0.2066P] 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 riding _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_abs_structure_Flack 0(10) _refine_ls_number_reflns 1571 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.8753(3) 0.0150(2) 0.23477(6) 0.0514(4) Uani 1 1 d . . . O2 O 1.1494(2) -0.07682(19) 0.17880(8) 0.0572(5) Uani 1 1 d . . . N1 N 0.8310(3) 0.05027(19) 0.14542(6) 0.0350(4) Uani 1 1 d . . . C1 C 0.4015(6) -0.0485(5) -0.00593(12) 0.1041(13) Uani 1 1 d . . . H1A H 0.4231 -0.0729 -0.0451 0.156 Uiso 1 1 calc R . . H1B H 0.2502 -0.0030 -0.0002 0.156 Uiso 1 1 calc R . . H1C H 0.4187 -0.1510 0.0155 0.156 Uiso 1 1 calc R . . C2 C 0.5729(6) 0.0752(4) 0.01233(10) 0.0763(9) Uani 1 1 d . . . H2 H 0.5734 0.1800 -0.0057 0.092 Uiso 1 1 calc R . . C3 C 0.7225(5) 0.0517(3) 0.05105(9) 0.0543(6) Uani 1 1 d . . . C4 C 0.8691(4) 0.0222(2) 0.08932(9) 0.0453(5) Uani 1 1 d . . . H4 H 1.0114 -0.0212 0.0786 0.054 Uiso 1 1 calc R . . C5 C 0.9693(3) -0.0099(2) 0.18537(9) 0.0389(5) Uani 1 1 d . . . C6 C 0.6571(4) 0.0886(3) 0.22905(8) 0.0420(5) Uani 1 1 d . . . H6A H 0.6483 0.1932 0.2504 0.050 Uiso 1 1 calc R . . H6B H 0.5392 0.0117 0.2426 0.050 Uiso 1 1 calc R . . C7 C 0.6247(3) 0.1236(2) 0.16714(8) 0.0306(4) Uani 1 1 d . . . H7 H 0.4907 0.0615 0.1530 0.037 Uiso 1 1 calc R . . C8 C 0.6017(3) 0.3067(2) 0.15388(7) 0.0278(4) Uani 1 1 d . . . C9 C 0.4060(3) 0.3676(2) 0.13056(8) 0.0383(5) Uani 1 1 d . . . H9 H 0.2874 0.2935 0.1211 0.046 Uiso 1 1 calc R . . C10 C 0.3819(4) 0.5371(3) 0.12082(9) 0.0482(5) Uani 1 1 d . . . H10 H 0.2462 0.5786 0.1052 0.058 Uiso 1 1 calc R . . C11 C 0.5535(4) 0.6444(3) 0.13363(9) 0.0439(5) Uani 1 1 d . . . H11 H 0.5369 0.7600 0.1268 0.053 Uiso 1 1 calc R . . C12 C 0.7498(4) 0.5849(3) 0.15639(9) 0.0420(5) Uani 1 1 d . . . H12 H 0.8689 0.6594 0.1651 0.050 Uiso 1 1 calc R . . C13 C 0.7741(3) 0.4162(2) 0.16669(8) 0.0349(4) Uani 1 1 d . . . H13 H 0.9096 0.3756 0.1826 0.042 Uiso 1 1 calc R . . 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 0.0484(9) 0.0620(10) 0.0438(9) 0.0061(7) -0.0113(7) 0.0071(9) O2 0.0305(7) 0.0481(9) 0.0930(12) 0.0014(8) -0.0054(8) 0.0041(7) N1 0.0353(8) 0.0301(8) 0.0396(9) 0.0023(7) 0.0049(7) 0.0063(7) C1 0.081(2) 0.184(4) 0.0468(16) -0.023(2) -0.0003(16) 0.005(3) C2 0.097(2) 0.096(2) 0.0364(13) 0.0032(14) 0.0078(15) 0.015(2) C3 0.0741(17) 0.0531(13) 0.0355(12) -0.0022(10) 0.0152(12) 0.0076(13) C4 0.0507(13) 0.0392(10) 0.0458(12) -0.0021(9) 0.0163(11) 0.0038(11) C5 0.0306(9) 0.0279(9) 0.0580(14) 0.0047(9) -0.0054(9) -0.0053(8) C6 0.0458(11) 0.0410(11) 0.0391(11) 0.0080(9) 0.0040(9) 0.0027(10) C7 0.0278(9) 0.0284(9) 0.0356(10) -0.0021(7) 0.0009(8) -0.0019(8) C8 0.0279(9) 0.0283(9) 0.0273(9) -0.0024(7) 0.0035(7) 0.0000(7) C9 0.0318(10) 0.0371(10) 0.0461(12) -0.0037(9) -0.0063(9) 0.0003(9) C10 0.0462(12) 0.0439(12) 0.0544(13) 0.0044(10) -0.0086(11) 0.0133(11) C11 0.0574(14) 0.0278(9) 0.0466(12) 0.0036(9) 0.0091(11) 0.0060(10) C12 0.0443(12) 0.0317(10) 0.0501(12) -0.0056(9) 0.0062(10) -0.0085(9) C13 0.0302(9) 0.0341(10) 0.0404(11) -0.0029(8) -0.0014(8) -0.0010(8) _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 C5 1.337(3) . ? O1 C6 1.430(3) . ? O2 C5 1.207(2) . ? N1 C5 1.359(3) . ? N1 C4 1.398(3) . ? N1 C7 1.457(2) . ? C1 C2 1.491(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.306(4) . ? C2 H2 0.9500 . ? C3 C4 1.294(3) . ? C4 H4 0.9500 . ? C6 C7 1.541(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.514(2) . ? C7 H7 1.0000 . ? C8 C9 1.382(3) . ? C8 C13 1.385(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 C11 1.371(3) . ? C10 H10 0.9500 . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 O1 C6 110.64(15) . . ? C5 N1 C4 122.63(18) . . ? C5 N1 C7 113.16(16) . . ? C4 N1 C7 123.59(17) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 125.5(3) . . ? C3 C2 H2 117.2 . . ? C1 C2 H2 117.2 . . ? C4 C3 C2 177.7(3) . . ? C3 C4 N1 124.1(2) . . ? C3 C4 H4 118.0 . . ? N1 C4 H4 118.0 . . ? O2 C5 O1 123.7(2) . . ? O2 C5 N1 126.8(2) . . ? O1 C5 N1 109.53(17) . . ? O1 C6 C7 106.46(16) . . ? O1 C6 H6A 110.4 . . ? C7 C6 H6A 110.4 . . ? O1 C6 H6B 110.4 . . ? C7 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? N1 C7 C8 113.14(15) . . ? N1 C7 C6 100.01(15) . . ? C8 C7 C6 113.36(15) . . ? N1 C7 H7 110.0 . . ? C8 C7 H7 110.0 . . ? C6 C7 H7 110.0 . . ? C9 C8 C13 119.12(17) . . ? C9 C8 C7 120.54(17) . . ? C13 C8 C7 120.30(17) . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.12(18) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 120.03(19) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C8 C13 C12 120.35(19) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? 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 C1 C2 C3 C4 15(6) . . . . ? C2 C3 C4 N1 -103(6) . . . . ? C5 N1 C4 C3 167.3(2) . . . . ? C7 N1 C4 C3 -3.0(3) . . . . ? C6 O1 C5 O2 -176.84(18) . . . . ? C6 O1 C5 N1 2.9(2) . . . . ? C4 N1 C5 O2 8.6(3) . . . . ? C7 N1 C5 O2 179.88(18) . . . . ? C4 N1 C5 O1 -171.09(17) . . . . ? C7 N1 C5 O1 0.2(2) . . . . ? C5 O1 C6 C7 -4.6(2) . . . . ? C5 N1 C7 C8 118.11(17) . . . . ? C4 N1 C7 C8 -70.7(2) . . . . ? C5 N1 C7 C6 -2.78(19) . . . . ? C4 N1 C7 C6 168.38(17) . . . . ? O1 C6 C7 N1 4.22(19) . . . . ? O1 C6 C7 C8 -116.50(17) . . . . ? N1 C7 C8 C9 129.30(19) . . . . ? C6 C7 C8 C9 -117.7(2) . . . . ? N1 C7 C8 C13 -52.8(2) . . . . ? C6 C7 C8 C13 60.1(2) . . . . ? C13 C8 C9 C10 -0.8(3) . . . . ? C7 C8 C9 C10 177.03(19) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C9 C8 C13 C12 0.2(3) . . . . ? C7 C8 C13 C12 -177.64(18) . . . . ? C11 C12 C13 C8 0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.184 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.030