data_ic12698 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N3 O' _chemical_formula_weight 251.28 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.454(2) _cell_length_b 13.7918(12) _cell_length_c 6.6660(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.678(3) _cell_angle_gamma 90.00 _cell_volume 2495.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 225 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 14.19 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 6448 _diffrn_reflns_av_R_equivalents 0.1283 _diffrn_reflns_av_sigmaI/netI 0.1311 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2193 _reflns_number_gt 902 _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^)+(0.1314P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.034(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2193 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2360 _refine_ls_R_factor_gt 0.1095 _refine_ls_wR_factor_ref 0.2988 _refine_ls_wR_factor_gt 0.2136 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.19210(19) 0.6406(3) 0.0884(6) 0.0810(17) Uani 1 1 d . . . N1 N 0.1149(3) 0.6340(4) -0.2153(8) 0.083(2) Uani 1 1 d . . . H1 H 0.1310 0.6492 -0.0951 0.100 Uiso 1 1 calc R . . N2 N 0.2753(3) 0.6052(3) -0.2635(7) 0.0719(18) Uani 1 1 d . . . N3 N 0.2751(3) 0.6319(3) 0.0688(7) 0.0713(19) Uani 1 1 d . . . C1 C 0.0651(4) 0.6347(5) -0.2672(11) 0.091(3) Uani 1 1 d . . . H1A H 0.0418 0.6499 -0.1799 0.109 Uiso 1 1 calc R . . C2 C 0.0545(3) 0.6094(5) -0.4678(10) 0.082(2) Uani 1 1 d . . . H2 H 0.0225 0.6050 -0.5446 0.098 Uiso 1 1 calc R . . C3 C 0.0985(3) 0.5915(4) -0.5396(11) 0.076(2) Uani 1 1 d . . . H3 H 0.1021 0.5727 -0.6737 0.092 Uiso 1 1 calc R . . C4 C 0.1362(4) 0.6060(4) -0.3797(10) 0.073(2) Uani 1 1 d . . . C5 C 0.1872(4) 0.5989(4) -0.3825(10) 0.076(2) Uani 1 1 d . . . H5 H 0.1961 0.5848 -0.5118 0.091 Uiso 1 1 calc R . . C6 C 0.2265(3) 0.6090(4) -0.2287(10) 0.071(2) Uani 1 1 d . . . C7 C 0.2262(4) 0.6278(4) -0.0114(10) 0.078(2) Uani 1 1 d . . . C8 C 0.3028(3) 0.6183(4) -0.0886(10) 0.074(2) Uani 1 1 d . . . C9 C 0.3564(4) 0.6241(4) -0.0606(9) 0.072(2) Uani 1 1 d . . . C10 C 0.3796(3) 0.6792(4) -0.1940(9) 0.069(2) Uani 1 1 d . . . H10 H 0.3603 0.7146 -0.2997 0.083 Uiso 1 1 calc R . . C11 C 0.4303(3) 0.6830(5) -0.1740(9) 0.073(2) Uani 1 1 d . . . H11 H 0.4455 0.7209 -0.2661 0.088 Uiso 1 1 calc R . . C12 C 0.4594(3) 0.6321(4) -0.0211(10) 0.081(2) Uani 1 1 d . . . H12 H 0.4944 0.6346 -0.0062 0.097 Uiso 1 1 calc R . . C13 C 0.4357(4) 0.5775(5) 0.1089(10) 0.090(3) Uani 1 1 d . . . H13 H 0.4551 0.5423 0.2144 0.109 Uiso 1 1 calc R . . C14 C 0.3857(4) 0.5719(5) 0.0927(10) 0.086(3) Uani 1 1 d . . . H14 H 0.3709 0.5330 0.1845 0.103 Uiso 1 1 calc R . . C15 C 0.2928(3) 0.6498(4) 0.2829(8) 0.076(2) Uani 1 1 d . . . H15A H 0.2683 0.6877 0.3417 0.115 Uiso 1 1 calc R . . H15B H 0.3239 0.6860 0.2963 0.115 Uiso 1 1 calc R . . H15C H 0.2983 0.5878 0.3546 0.115 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 0.157(5) 0.054(3) 0.044(3) -0.012(2) 0.052(3) -0.042(3) N1 0.169(7) 0.043(3) 0.048(4) -0.007(3) 0.049(4) -0.025(4) N2 0.150(6) 0.047(3) 0.028(3) -0.011(2) 0.044(3) -0.029(3) N3 0.152(6) 0.042(3) 0.029(3) -0.012(2) 0.043(3) -0.038(4) C1 0.175(9) 0.051(4) 0.056(5) 0.004(4) 0.048(6) -0.003(6) C2 0.138(7) 0.057(5) 0.055(5) -0.001(4) 0.026(5) 0.008(4) C3 0.143(7) 0.042(4) 0.047(4) -0.004(3) 0.027(5) -0.019(4) C4 0.150(8) 0.038(4) 0.044(4) -0.008(3) 0.053(5) -0.034(4) C5 0.165(8) 0.039(4) 0.034(4) -0.010(3) 0.048(5) -0.037(4) C6 0.147(7) 0.040(4) 0.035(4) -0.009(3) 0.045(5) -0.033(4) C7 0.156(8) 0.045(4) 0.043(4) -0.009(3) 0.043(5) -0.046(5) C8 0.156(8) 0.038(4) 0.037(4) -0.006(3) 0.048(5) -0.035(4) C9 0.153(7) 0.039(4) 0.032(4) -0.011(3) 0.043(4) -0.024(4) C10 0.130(7) 0.039(4) 0.046(4) -0.005(3) 0.040(4) -0.017(4) C11 0.135(7) 0.047(4) 0.046(4) 0.002(3) 0.041(5) -0.009(4) C12 0.157(7) 0.046(4) 0.046(4) 0.000(3) 0.035(4) -0.005(4) C13 0.179(9) 0.050(4) 0.047(4) 0.002(3) 0.032(6) -0.012(6) C14 0.188(9) 0.041(4) 0.037(4) -0.005(3) 0.046(5) -0.026(5) C15 0.162(7) 0.046(4) 0.025(3) -0.012(3) 0.029(4) -0.033(4) _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 C7 1.240(8) . ? N1 C1 1.360(9) . ? N1 C4 1.373(8) . ? N2 C8 1.302(8) . ? N2 C6 1.393(9) . ? N3 C7 1.370(9) . ? N3 C8 1.398(8) . ? N3 C15 1.458(7) . ? C1 C2 1.370(9) . ? C2 C3 1.388(9) . ? C3 C4 1.384(9) . ? C4 C5 1.407(10) . ? C5 C6 1.379(9) . ? C6 C7 1.473(9) . ? C8 C9 1.459(10) . ? C9 C10 1.394(9) . ? C9 C14 1.400(10) . ? C10 C11 1.380(9) . ? C11 C12 1.387(9) . ? C12 C13 1.383(10) . ? C13 C14 1.362(10) . ? 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 C1 N1 C4 109.4(7) . . ? C8 N2 C6 106.7(6) . . ? C7 N3 C8 108.3(6) . . ? C7 N3 C15 123.6(5) . . ? C8 N3 C15 128.2(7) . . ? N1 C1 C2 107.7(8) . . ? C1 C2 C3 108.3(8) . . ? C4 C3 C2 107.4(7) . . ? N1 C4 C3 107.2(8) . . ? N1 C4 C5 125.1(8) . . ? C3 C4 C5 127.6(7) . . ? C6 C5 C4 130.7(6) . . ? C5 C6 N2 122.4(6) . . ? C5 C6 C7 128.9(8) . . ? N2 C6 C7 108.6(8) . . ? O1 C7 N3 124.0(6) . . ? O1 C7 C6 132.1(9) . . ? N3 C7 C6 103.9(7) . . ? N2 C8 N3 112.5(7) . . ? N2 C8 C9 124.0(6) . . ? N3 C8 C9 123.4(7) . . ? C10 C9 C14 118.6(8) . . ? C10 C9 C8 119.8(7) . . ? C14 C9 C8 121.5(7) . . ? C11 C10 C9 120.6(7) . . ? C10 C11 C12 120.8(7) . . ? C13 C12 C11 117.5(8) . . ? C14 C13 C12 123.1(8) . . ? C13 C14 C9 119.3(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.613 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.234