data_z2d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N O2' _chemical_formula_weight 201.22 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9990(4) _cell_length_b 11.1539(11) _cell_length_c 12.2250(10) _cell_angle_alpha 71.924(5) _cell_angle_beta 89.510(8) _cell_angle_gamma 81.010(5) _cell_volume 511.55(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method 'CCD' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2965 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1765 _reflns_number_gt 1410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL v.6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0641P)^2^+0.2572P] 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 1765 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1200 _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 C1 C 0.4858(6) 0.07321(19) 0.12754(18) 0.0323(5) Uani 1 1 d . . . H1A H 0.7292 0.0702 0.1156 0.048 Uiso 1 1 calc R . . H1B H 0.4302 -0.0133 0.1467 0.048 Uiso 1 1 calc R . . H1C H 0.4254 0.1078 0.1909 0.048 Uiso 1 1 calc R . . C2 C 0.3279(5) 0.27857(18) -0.00736(17) 0.0249(5) Uani 1 1 d . . . C3 C 0.1427(5) 0.35241(18) -0.11879(16) 0.0238(5) Uani 1 1 d . . . N1 N -0.1611(5) 0.22223(16) -0.21682(16) 0.0335(5) Uani 1 1 d . . . C5 C 0.1481(5) 0.47909(18) -0.16121(17) 0.0243(4) Uani 1 1 d . . . H5 H 0.2618 0.5126 -0.1122 0.029 Uiso 1 1 calc R . . C6 C 0.0098(5) 0.57340(18) -0.26915(17) 0.0242(4) Uani 1 1 d . . . C7 C -0.1471(5) 0.54636(19) -0.35919(17) 0.0272(5) Uani 1 1 d . . . H7 H -0.1752 0.4610 -0.3509 0.033 Uiso 1 1 calc R . . C8 C -0.2610(5) 0.64284(19) -0.45975(18) 0.0282(5) Uani 1 1 d . . . H8 H -0.3654 0.6224 -0.5197 0.034 Uiso 1 1 calc R . . C9 C -0.2264(5) 0.76950(18) -0.47530(17) 0.0254(5) Uani 1 1 d . . . C10 C -0.0700(5) 0.79631(18) -0.38604(18) 0.0269(5) Uani 1 1 d . . . H10 H -0.0434 0.8819 -0.3946 0.032 Uiso 1 1 calc R . . C11 C 0.0474(5) 0.70039(18) -0.28505(17) 0.0259(5) Uani 1 1 d . . . H11 H 0.1548 0.7211 -0.2258 0.031 Uiso 1 1 calc R . . C12 C -0.3525(5) 0.87286(19) -0.58534(18) 0.0305(5) Uani 1 1 d . . . H12A H -0.3951 0.9556 -0.5712 0.046 Uiso 1 1 calc R . . H12B H -0.5632 0.8554 -0.6131 0.046 Uiso 1 1 calc R . . H12C H -0.1814 0.8750 -0.6435 0.046 Uiso 1 1 calc R . . C4 C -0.0238(5) 0.28056(18) -0.17431(17) 0.0259(5) Uani 1 1 d . . . O1 O 0.2973(3) 0.15437(12) 0.02326(12) 0.0275(4) Uani 1 1 d . . . O2 O 0.4892(4) 0.32394(13) 0.04813(12) 0.0331(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 0.0399(12) 0.0234(10) 0.0296(11) -0.0028(8) -0.0026(9) -0.0045(9) C2 0.0261(10) 0.0227(10) 0.0259(11) -0.0078(8) 0.0038(8) -0.0039(8) C3 0.0257(10) 0.0227(10) 0.0247(11) -0.0095(8) 0.0038(8) -0.0050(8) N1 0.0387(11) 0.0270(9) 0.0360(11) -0.0111(8) -0.0012(8) -0.0064(8) C5 0.0261(10) 0.0242(10) 0.0247(10) -0.0106(8) 0.0035(8) -0.0046(7) C6 0.0234(10) 0.0232(10) 0.0264(11) -0.0084(8) 0.0025(8) -0.0033(8) C7 0.0315(11) 0.0246(10) 0.0289(11) -0.0122(8) 0.0010(9) -0.0065(8) C8 0.0303(11) 0.0298(11) 0.0264(11) -0.0118(8) -0.0020(8) -0.0047(8) C9 0.0233(10) 0.0270(10) 0.0258(11) -0.0086(8) 0.0019(8) -0.0027(8) C10 0.0303(11) 0.0196(9) 0.0311(11) -0.0083(8) 0.0002(9) -0.0040(8) C11 0.0283(10) 0.0247(10) 0.0265(11) -0.0104(8) 0.0003(8) -0.0053(8) C12 0.0335(11) 0.0278(11) 0.0282(11) -0.0079(9) -0.0017(9) -0.0007(8) C4 0.0283(11) 0.0216(10) 0.0270(11) -0.0066(8) 0.0030(8) -0.0040(8) O1 0.0341(8) 0.0198(7) 0.0270(8) -0.0039(6) -0.0018(6) -0.0061(6) O2 0.0456(9) 0.0254(7) 0.0296(8) -0.0080(6) -0.0063(7) -0.0104(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 C1 O1 1.449(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O2 1.206(2) . ? C2 O1 1.343(2) . ? C2 C3 1.488(3) . ? C3 C5 1.349(3) . ? C3 C4 1.435(3) . ? N1 C4 1.149(3) . ? C5 C6 1.457(3) . ? C5 H5 0.9500 . ? C6 C11 1.401(3) . ? C6 C7 1.405(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.394(3) . ? C9 C12 1.504(3) . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 124.03(18) . . ? O2 C2 C3 124.37(17) . . ? O1 C2 C3 111.59(16) . . ? C5 C3 C4 124.99(18) . . ? C5 C3 C2 118.80(17) . . ? C4 C3 C2 116.19(16) . . ? C3 C5 C6 131.20(19) . . ? C3 C5 H5 114.4 . . ? C6 C5 H5 114.4 . . ? C11 C6 C7 117.86(17) . . ? C11 C6 C5 116.85(18) . . ? C7 C6 C5 125.26(17) . . ? C8 C7 C6 120.59(18) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.60(19) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 117.80(18) . . ? C10 C9 C12 121.52(18) . . ? C8 C9 C12 120.68(18) . . ? C11 C10 C9 121.20(18) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 120.93(18) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C4 C3 178.6(2) . . ? C2 O1 C1 115.60(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 O2 C2 C3 C5 -1.1(3) . . . . ? O1 C2 C3 C5 179.77(16) . . . . ? O2 C2 C3 C4 177.59(19) . . . . ? O1 C2 C3 C4 -1.6(2) . . . . ? C4 C3 C5 C6 -2.5(3) . . . . ? C2 C3 C5 C6 176.06(18) . . . . ? C3 C5 C6 C11 177.33(19) . . . . ? C3 C5 C6 C7 -4.8(3) . . . . ? C11 C6 C7 C8 -0.3(3) . . . . ? C5 C6 C7 C8 -178.06(18) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C7 C8 C9 C12 -179.94(19) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C12 C9 C10 C11 -179.63(18) . . . . ? C9 C10 C11 C6 -0.5(3) . . . . ? C7 C6 C11 C10 0.7(3) . . . . ? C5 C6 C11 C10 178.67(18) . . . . ? C5 C3 C4 N1 -122(9) . . . . ? C2 C3 C4 N1 59(9) . . . . ? O2 C2 O1 C1 -2.6(3) . . . . ? C3 C2 O1 C1 176.56(16) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.215 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.055