data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 N5 O2' _chemical_formula_sum 'C19 H13 N5 O2' _chemical_formula_weight 343.34 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 'Tetragonal' _symmetry_space_group_name_H-M 'P-42(1)c ' _symmetry_space_group_name_Hall 'P-42n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 22.6533(16) _cell_length_b 22.6533(16) _cell_length_c 7.2430(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3716.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2078 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 23.04 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'TRIUMPH curved crystal monochromator' _diffrn_measurement_device_type 'PHOTON 100 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11161 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3266 _reflns_number_gt 1888 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0953P)^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 0.038(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(3) _refine_ls_number_reflns 3266 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1793 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.23162(19) 0.5904(2) 0.8186(7) 0.0611(12) Uani 1 1 d . . . C2 C 0.29389(17) 0.60572(16) 0.8824(6) 0.0523(11) Uani 1 1 d . . . H2 H 0.3167 0.6191 0.7752 0.063 Uiso 1 1 calc R . . C3 C 0.28418(16) 0.65827(16) 1.0104(6) 0.0513(10) Uani 1 1 d . . . H3 H 0.2852 0.6437 1.1377 0.062 Uiso 1 1 calc R . . C4 C 0.22140(18) 0.67846(18) 0.9695(7) 0.0584(12) Uani 1 1 d . . . C5 C 0.13053(19) 0.6350(2) 0.8338(8) 0.0763(15) Uani 1 1 d . . . H5A H 0.1201 0.5992 0.7710 0.114 Uiso 1 1 calc R . . H5B H 0.1222 0.6682 0.7555 0.114 Uiso 1 1 calc R . . H5C H 0.1080 0.6383 0.9455 0.114 Uiso 1 1 calc R . . C6 C 0.32567(18) 0.55493(16) 0.9692(7) 0.0546(11) Uani 1 1 d . . . C7 C 0.3256(2) 0.53489(19) 1.1524(7) 0.0674(13) Uani 1 1 d . . . H7 H 0.3054 0.5513 1.2516 0.081 Uiso 1 1 calc R . . C8 C 0.3618(2) 0.4856(2) 1.1556(9) 0.0767(14) Uani 1 1 d . . . H8 H 0.3694 0.4628 1.2598 0.092 Uiso 1 1 calc R . . C9 C 0.3843(2) 0.4752(2) 0.9886(10) 0.0775(16) Uani 1 1 d . . . H9 H 0.4103 0.4451 0.9570 0.093 Uiso 1 1 calc R . . C10 C 0.3732(3) 0.5205(2) 0.6724(8) 0.0854(16) Uani 1 1 d . . . H10A H 0.3998 0.4894 0.6382 0.128 Uiso 1 1 calc R . . H10B H 0.3906 0.5580 0.6425 0.128 Uiso 1 1 calc R . . H10C H 0.3367 0.5161 0.6062 0.128 Uiso 1 1 calc R . . C11 C 0.38114(17) 0.77476(17) 0.7970(6) 0.0515(11) Uani 1 1 d . . . C12 C 0.42286(18) 0.78536(18) 0.9336(6) 0.0531(11) Uani 1 1 d . . . C13 C 0.41745(18) 0.75708(17) 1.1036(7) 0.0563(11) Uani 1 1 d . . . H13 H 0.4441 0.7647 1.1983 0.068 Uiso 1 1 calc R . . C14 C 0.37170(16) 0.71736(16) 1.1292(6) 0.0502(10) Uani 1 1 d . . . C15 C 0.33052(15) 0.70588(16) 0.9921(7) 0.0503(10) Uani 1 1 d . . . C16 C 0.33550(18) 0.73627(17) 0.8249(6) 0.0543(11) Uani 1 1 d . . . H16 H 0.3077 0.7303 0.7323 0.065 Uiso 1 1 calc R . . C17 C 0.38634(19) 0.80484(19) 0.6216(8) 0.0619(12) Uani 1 1 d . . . C18 C 0.4721(2) 0.8234(2) 0.9026(8) 0.0725(14) Uani 1 1 d . . . C19 C 0.36944(19) 0.6874(2) 1.3034(7) 0.0579(11) Uani 1 1 d . . . N1 N 0.19431(14) 0.63409(15) 0.8790(5) 0.0570(9) Uani 1 1 d . . . N2 N 0.36166(16) 0.51773(15) 0.8709(6) 0.0644(11) Uani 1 1 d . . . N3 N 0.39059(19) 0.82721(19) 0.4804(8) 0.0851(13) Uani 1 1 d . . . N4 N 0.5122(2) 0.8526(2) 0.8721(8) 0.1137(18) Uani 1 1 d . . . N5 N 0.36784(18) 0.66181(19) 1.4422(6) 0.0761(12) Uani 1 1 d . . . O1 O 0.21803(15) 0.54819(13) 0.7284(5) 0.0762(10) Uani 1 1 d . . . O2 O 0.19922(12) 0.72485(14) 1.0159(5) 0.0726(9) 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 0.068(3) 0.050(3) 0.065(3) 0.015(2) -0.016(2) -0.004(2) C2 0.060(2) 0.043(2) 0.054(3) 0.002(2) -0.005(2) 0.0005(17) C3 0.056(2) 0.047(2) 0.051(3) -0.001(2) 0.000(2) 0.0002(17) C4 0.052(2) 0.053(3) 0.070(3) 0.011(2) 0.001(2) -0.007(2) C5 0.053(3) 0.097(3) 0.078(4) 0.022(3) -0.012(3) -0.012(2) C6 0.056(2) 0.046(2) 0.062(3) 0.004(2) -0.004(2) 0.0021(18) C7 0.086(3) 0.060(3) 0.056(3) 0.010(2) -0.007(3) 0.004(2) C8 0.084(3) 0.064(3) 0.083(4) 0.008(3) -0.007(3) 0.011(2) C9 0.075(3) 0.048(3) 0.110(5) 0.002(3) -0.013(3) 0.009(2) C10 0.118(4) 0.074(3) 0.064(4) -0.005(3) 0.022(3) -0.003(3) C11 0.051(2) 0.050(2) 0.053(3) 0.009(2) 0.002(2) 0.0011(18) C12 0.049(2) 0.058(2) 0.053(3) 0.001(2) 0.003(2) -0.0038(19) C13 0.050(2) 0.063(3) 0.056(3) -0.002(2) -0.004(2) -0.0027(19) C14 0.046(2) 0.054(2) 0.051(3) 0.004(2) -0.002(2) 0.0035(18) C15 0.044(2) 0.048(2) 0.059(3) 0.002(2) -0.001(2) 0.0009(17) C16 0.060(3) 0.056(2) 0.047(3) -0.001(2) -0.003(2) 0.004(2) C17 0.063(3) 0.053(2) 0.070(4) 0.006(3) 0.001(3) -0.0027(19) C18 0.055(3) 0.091(3) 0.072(4) 0.002(3) -0.005(3) -0.010(2) C19 0.057(3) 0.059(3) 0.058(3) -0.001(2) -0.001(2) -0.003(2) N1 0.0487(19) 0.062(2) 0.060(2) 0.009(2) -0.0081(18) -0.0027(17) N2 0.069(2) 0.049(2) 0.076(3) -0.002(2) -0.004(2) -0.0004(17) N3 0.094(3) 0.084(3) 0.077(3) 0.025(3) 0.007(3) 0.001(2) N4 0.076(3) 0.141(4) 0.124(4) 0.037(4) -0.001(3) -0.041(3) N5 0.083(3) 0.080(3) 0.065(3) 0.003(3) -0.004(2) 0.000(2) O1 0.100(2) 0.0556(19) 0.073(2) -0.0011(17) -0.023(2) -0.0106(17) O2 0.0613(18) 0.0639(19) 0.093(3) 0.0008(19) 0.0021(18) 0.0073(15) _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 1.198(5) . ? C1 N1 1.374(6) . ? C1 C2 1.525(6) . ? C2 C6 1.496(5) . ? C2 C3 1.525(5) . ? C2 H2 0.9800 . ? C3 C15 1.511(5) . ? C3 C4 1.523(6) . ? C3 H3 0.9800 . ? C4 O2 1.212(5) . ? C4 N1 1.348(5) . ? C5 N1 1.482(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N2 1.372(5) . ? C6 C7 1.402(7) . ? C7 C8 1.387(7) . ? C7 H7 0.9300 . ? C8 C9 1.333(8) . ? C8 H8 0.9300 . ? C9 N2 1.384(6) . ? C9 H9 0.9300 . ? C10 N2 1.462(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.367(5) . ? C11 C12 1.389(6) . ? C11 C17 1.446(7) . ? C12 C13 1.393(6) . ? C12 C18 1.426(6) . ? C13 C14 1.385(5) . ? C13 H13 0.9300 . ? C14 C15 1.387(6) . ? C14 C19 1.434(7) . ? C15 C16 1.398(6) . ? C16 H16 0.9300 . ? C17 N3 1.146(6) . ? C18 N4 1.145(6) . ? C19 N5 1.160(5) . ? 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 N1 126.2(4) . . ? O1 C1 C2 125.8(4) . . ? N1 C1 C2 107.9(4) . . ? C6 C2 C3 114.5(4) . . ? C6 C2 C1 113.4(3) . . ? C3 C2 C1 103.2(3) . . ? C6 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? C15 C3 C4 114.7(3) . . ? C15 C3 C2 113.8(3) . . ? C4 C3 C2 104.6(3) . . ? C15 C3 H3 107.8 . . ? C4 C3 H3 107.8 . . ? C2 C3 H3 107.8 . . ? O2 C4 N1 126.3(4) . . ? O2 C4 C3 126.4(4) . . ? N1 C4 C3 107.2(4) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 107.0(4) . . ? N2 C6 C2 122.7(4) . . ? C7 C6 C2 130.3(4) . . ? C8 C7 C6 106.0(5) . . ? C8 C7 H7 127.0 . . ? C6 C7 H7 127.0 . . ? C9 C8 C7 110.6(5) . . ? C9 C8 H8 124.7 . . ? C7 C8 H8 124.7 . . ? C8 C9 N2 107.2(4) . . ? C8 C9 H9 126.4 . . ? N2 C9 H9 126.4 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 121.3(4) . . ? C16 C11 C17 119.5(4) . . ? C12 C11 C17 119.3(4) . . ? C11 C12 C13 119.3(4) . . ? C11 C12 C18 121.6(4) . . ? C13 C12 C18 119.1(4) . . ? C14 C13 C12 118.9(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 122.0(4) . . ? C13 C14 C19 116.9(4) . . ? C15 C14 C19 121.1(4) . . ? C14 C15 C16 118.3(4) . . ? C14 C15 C3 122.6(4) . . ? C16 C15 C3 118.9(4) . . ? C11 C16 C15 120.2(4) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N3 C17 C11 178.1(5) . . ? N4 C18 C12 177.4(6) . . ? N5 C19 C14 178.4(5) . . ? C4 N1 C1 114.4(4) . . ? C4 N1 C5 122.7(4) . . ? C1 N1 C5 122.7(4) . . ? C6 N2 C9 109.1(4) . . ? C6 N2 C10 126.1(4) . . ? C9 N2 C10 124.7(4) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.001 12 0 ' ' 2 0.000 0.500 -0.048 200 11 ' ' 3 0.500 0.000 -0.009 200 11 ' ' 4 0.500 0.500 0.217 11 1 ' ' 5 0.000 0.000 0.303 10 1 ' ' 6 0.500 0.500 0.519 10 0 ' ' 7 0.000 0.000 0.696 9 1 ' ' 8 0.500 0.500 0.803 10 1 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.257 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.067