data_APH _audit_creation_date 2016-11-02 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H9 N3 O' _chemical_formula_sum 'C7 H9 N3 O' _chemical_formula_weight 151.17 _chemical_melting_point ? _chemical_oxdiff_formula 'C10 H9 O2 N2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.4473(11) _cell_length_b 13.907(3) _cell_length_c 10.057(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.69(2) _cell_angle_gamma 90.00 _cell_volume 743.3(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 995 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.4500 _cell_measurement_theta_min 5.6230 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description '' _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_unetI/netI 0.0505 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2415 _diffrn_reflns_theta_full 70.84 _diffrn_reflns_theta_max 70.84 _diffrn_reflns_theta_min 5.52 _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1640 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9929 _diffrn_measured_fraction_theta_max 0.9654 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 33.00 62.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -30.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega 63.00 123.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -30.0000 60 #__ type_ start__ end____ width___ exp.time_ 3 omega 64.00 122.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -90.0000 58 #__ type_ start__ end____ width___ exp.time_ 4 omega 71.00 119.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -150.0000 48 #__ type_ start__ end____ width___ exp.time_ 5 omega 37.00 62.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega -4.00 21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 49.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 90.0000 44 #__ type_ start__ end____ width___ exp.time_ 8 omega 114.00 150.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 12.0000 90.0000 36 #__ type_ start__ end____ width___ exp.time_ 9 omega 58.00 108.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 12.0000 90.0000 50 #__ type_ start__ end____ width___ exp.time_ 10 omega 51.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 30.0000 41 #__ type_ start__ end____ width___ exp.time_ 11 omega 44.00 100.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 30.0000 56 #__ type_ start__ end____ width___ exp.time_ 12 omega 36.00 61.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -37.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 13 omega 38.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -37.0000 -90.0000 38 #__ type_ start__ end____ width___ exp.time_ 14 omega 55.00 123.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 -150.0000 68 #__ type_ start__ end____ width___ exp.time_ 15 omega 39.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -120.0000 75 #__ type_ start__ end____ width___ exp.time_ 16 omega 39.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -37.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 17 omega 30.00 84.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -77.0000 -180.0000 54 #__ type_ start__ end____ width___ exp.time_ 18 omega -60.00 -26.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 -120.0000 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1156324000 _diffrn_orient_matrix_UB_12 -0.0182701000 _diffrn_orient_matrix_UB_13 -0.1519646000 _diffrn_orient_matrix_UB_21 0.2559469000 _diffrn_orient_matrix_UB_22 0.0213221000 _diffrn_orient_matrix_UB_23 -0.0349448000 _diffrn_orient_matrix_UB_31 0.0704174000 _diffrn_orient_matrix_UB_32 -0.1072421000 _diffrn_orient_matrix_UB_33 0.0186580000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1091 _reflns_number_total 1385 _reflns_odcompleteness_completeness 99.29 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.452 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.115 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 132 _refine_ls_number_reflns 1385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.1022 _refine_ls_restrained_S_all 1.191 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2795 _refine_ls_wR_factor_ref 0.3050 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.1621(5) 0.50237(16) 0.2883(2) 0.0665(9) Uani 1 1 d . . . N2 N 0.3173(5) 0.51365(18) 0.1022(3) 0.0522(8) Uani 1 1 d . . . C3 C -0.2321(5) 0.8108(2) 0.0804(3) 0.0468(8) Uani 1 1 d . . . N4 N 0.4695(5) 0.4314(2) 0.1337(3) 0.0549(8) Uani 1 1 d . . . C5 C 0.1735(5) 0.5470(2) 0.1843(2) 0.0445(8) Uani 1 1 d . . . C6 C 0.0355(5) 0.6372(2) 0.1434(3) 0.0431(8) Uani 1 1 d . . . N7 N -0.3507(6) 0.8967(2) 0.0534(3) 0.0653(9) Uani 1 1 d . . . C8 C 0.0808(5) 0.6976(2) 0.0409(3) 0.0499(8) Uani 1 1 d . . . C9 C -0.1478(5) 0.6652(2) 0.2129(3) 0.0475(8) Uani 1 1 d . . . C10 C -0.0485(5) 0.7826(2) 0.0098(3) 0.0520(9) Uani 1 1 d . . . C11 C -0.2792(5) 0.7495(2) 0.1817(3) 0.0503(8) Uani 1 1 d . . . H11 H -0.4018 0.7660 0.2290 0.060 Uiso 1 1 calc R . . H4A H 0.375(8) 0.379(3) 0.124(4) 0.083(13) Uiso 1 1 d . . . H9 H -0.178(5) 0.624(2) 0.286(3) 0.046(7) Uiso 1 1 d . . . H7A H -0.322(6) 0.934(2) -0.018(3) 0.052(9) Uiso 1 1 d . . . H10 H -0.025(6) 0.823(2) -0.064(3) 0.051(8) Uiso 1 1 d . . . H2 H 0.334(6) 0.550(2) 0.030(3) 0.048(8) Uiso 1 1 d . . . H8 H 0.202(7) 0.675(3) -0.018(4) 0.070(10) Uiso 1 1 d . . . H4B H 0.535(9) 0.433(3) 0.216(5) 0.090(14) Uiso 1 1 d . . . H7B H -0.446(8) 0.922(3) 0.103(4) 0.069(10) 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 O1 0.0786(16) 0.0583(16) 0.0696(15) 0.0166(10) 0.0316(12) 0.0143(11) N2 0.0527(13) 0.0511(16) 0.0551(13) 0.0119(11) 0.0165(10) 0.0189(11) C3 0.0404(14) 0.0472(17) 0.0493(13) -0.0046(11) 0.0024(10) 0.0079(11) N4 0.0551(14) 0.0490(17) 0.0596(15) 0.0085(12) 0.0106(11) 0.0155(12) C5 0.0392(13) 0.0449(16) 0.0496(14) 0.0001(11) 0.0099(10) -0.0009(10) C6 0.0354(12) 0.0423(16) 0.0498(14) -0.0038(11) 0.0052(10) 0.0021(10) N7 0.0722(17) 0.063(2) 0.0640(17) 0.0064(13) 0.0226(14) 0.0271(14) C8 0.0450(14) 0.0509(18) 0.0553(15) 0.0025(12) 0.0142(11) 0.0088(12) C9 0.0410(14) 0.0530(19) 0.0485(14) 0.0010(11) 0.0102(11) 0.0022(11) C10 0.0532(15) 0.0494(18) 0.0552(16) 0.0064(12) 0.0158(12) 0.0099(13) C11 0.0389(13) 0.059(2) 0.0527(14) -0.0061(12) 0.0100(11) 0.0068(11) _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 1.229(3) . ? N2 N4 1.408(3) . ? N2 C5 1.339(4) . ? C3 N7 1.357(4) . ? C3 C10 1.403(4) . ? C3 C11 1.395(4) . ? C5 C6 1.474(4) . ? C6 C8 1.393(4) . ? C6 C9 1.394(4) . ? C8 C10 1.377(4) . ? C9 C11 1.373(4) . ? 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 N2 N4 122.5(2) . . ? N7 C3 C10 120.4(3) . . ? N7 C3 C11 121.9(3) . . ? C11 C3 C10 117.7(3) . . ? O1 C5 N2 119.7(3) . . ? O1 C5 C6 123.3(2) . . ? N2 C5 C6 117.0(2) . . ? C8 C6 C5 123.9(2) . . ? C8 C6 C9 117.7(3) . . ? C9 C6 C5 118.4(2) . . ? C10 C8 C6 121.4(2) . . ? C11 C9 C6 121.3(3) . . ? C8 C10 C3 120.7(3) . . ? C9 C11 C3 121.2(2) . . ?