#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 15 _journal_issue 2 _journal_year 2024 _journal_page_first 143 _journal_page_last 148 #============================================================================= data_gbbb61 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c] pyrazole-5-carbonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N4 O' _chemical_formula_sum 'C14 H12 N4 O' _chemical_formula_weight 252.28 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 Triclinic _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4788(7) _cell_length_b 8.8433(7) _cell_length_c 10.7377(9) _cell_angle_alpha 103.456(7) _cell_angle_beta 99.207(8) _cell_angle_gamma 92.451(8) _cell_volume 588.55(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1276 _cell_measurement_theta_min 3.8140 _cell_measurement_theta_max 28.6140 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.94352 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Crys Alis RED' _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1049 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3695 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2073 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction,2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction,2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction,2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 2012)' _computing_publication_material 'PLATON (Spek,2009)' _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^)+(0.0465P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2073 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 N1 N 0.2854(3) 0.32352(19) 1.09301(16) 0.0360(5) Uani 1 1 d . . . N2 N 0.1315(3) 0.2434(2) 1.13065(18) 0.0368(5) Uani 1 1 d . . . C3 C -0.0503(3) 0.2116(2) 1.0436(2) 0.0318(5) Uani 1 1 d . . . C3A C -0.0154(3) 0.2747(2) 0.94204(19) 0.0292(5) Uani 1 1 d . . . C4 C -0.1512(3) 0.2811(2) 0.81664(19) 0.0292(5) Uani 1 1 d . . . H4 H -0.2742 0.3367 0.8363 0.035 Uiso 1 1 calc R . . C5 C -0.0199(3) 0.3762(2) 0.75115(19) 0.0308(5) Uani 1 1 d . . . C6 C 0.1836(4) 0.4309(2) 0.79366(19) 0.0319(5) Uani 1 1 d . . . O7 O 0.2992(2) 0.41403(16) 0.90823(13) 0.0385(4) Uani 1 1 d . . . C7A C 0.1900(3) 0.3386(2) 0.9789(2) 0.0300(5) Uani 1 1 d . . . C8 C -0.2253(3) 0.1189(2) 0.73034(19) 0.0285(5) Uani 1 1 d . . . C9 C -0.4317(4) 0.0602(2) 0.7152(2) 0.0393(6) Uani 1 1 d . . . H9 H -0.5261 0.1213 0.7564 0.047 Uiso 1 1 calc R . . C10 C -0.4997(4) -0.0885(3) 0.6394(2) 0.0474(7) Uani 1 1 d . . . H10 H -0.6387 -0.1265 0.6304 0.057 Uiso 1 1 calc R . . C11 C -0.3620(4) -0.1800(2) 0.5774(2) 0.0435(6) Uani 1 1 d . . . H11 H -0.4075 -0.2797 0.5265 0.052 Uiso 1 1 calc R . . C12 C -0.1571(4) -0.1231(2) 0.5911(2) 0.0427(6) Uani 1 1 d . . . H12 H -0.0632 -0.1844 0.5496 0.051 Uiso 1 1 calc R . . C13 C -0.0897(4) 0.0256(2) 0.6668(2) 0.0358(6) Uani 1 1 d . . . H13 H 0.0493 0.0634 0.6749 0.043 Uiso 1 1 calc R . . C14 C -0.2370(4) 0.1247(2) 1.0662(2) 0.0427(6) Uani 1 1 d . . . H14A H -0.2563 0.0221 1.0091 0.064 Uiso 1 1 calc R . . H14B H -0.3592 0.1794 1.0493 0.064 Uiso 1 1 calc R . . H14C H -0.2160 0.1165 1.1549 0.064 Uiso 1 1 calc R . . C15 C -0.1210(4) 0.4109(2) 0.6354(2) 0.0338(6) Uani 1 1 d . . . N16 N -0.2052(3) 0.4368(2) 0.54097(19) 0.0493(6) Uani 1 1 d . . . N17 N 0.3069(3) 0.5064(2) 0.7337(2) 0.0430(6) Uani 1 1 d . . . H171 H 0.428(4) 0.557(3) 0.776(2) 0.067(9) Uiso 1 1 d . . . H172 H 0.261(4) 0.521(2) 0.652(2) 0.054(7) Uiso 1 1 d . . . H2 H 0.160(4) 0.219(3) 1.210(2) 0.067(8) 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 N1 0.0292(12) 0.0458(10) 0.0334(11) 0.0145(8) 0.0007(8) -0.0013(9) N2 0.0374(13) 0.0420(10) 0.0321(11) 0.0146(9) 0.0023(9) -0.0008(9) C3 0.0314(14) 0.0314(11) 0.0314(12) 0.0060(9) 0.0047(10) 0.0020(10) C3A 0.0282(13) 0.0285(10) 0.0297(12) 0.0073(9) 0.0016(9) 0.0018(9) C4 0.0248(13) 0.0307(11) 0.0315(12) 0.0086(9) 0.0018(9) 0.0001(9) C5 0.0296(14) 0.0300(11) 0.0306(12) 0.0090(9) -0.0018(10) -0.0035(10) C6 0.0370(15) 0.0314(11) 0.0257(12) 0.0083(9) -0.0006(10) 0.0001(10) O7 0.0275(10) 0.0536(9) 0.0348(9) 0.0186(7) -0.0022(7) -0.0075(7) C7A 0.0275(14) 0.0328(11) 0.0292(12) 0.0099(9) 0.0012(9) -0.0022(10) C8 0.0262(13) 0.0305(11) 0.0280(11) 0.0100(9) -0.0005(9) -0.0015(10) C9 0.0276(14) 0.0413(12) 0.0450(14) 0.0043(10) 0.0040(11) 0.0005(10) C10 0.0330(16) 0.0507(14) 0.0519(15) 0.0086(12) -0.0015(12) -0.0130(12) C11 0.0505(18) 0.0367(12) 0.0365(13) 0.0056(10) -0.0043(12) -0.0094(12) C12 0.0479(18) 0.0379(12) 0.0412(14) 0.0059(10) 0.0097(12) 0.0043(12) C13 0.0279(14) 0.0395(12) 0.0388(13) 0.0095(10) 0.0041(10) -0.0022(10) C14 0.0382(16) 0.0477(13) 0.0448(14) 0.0162(11) 0.0096(11) -0.0025(11) C15 0.0307(14) 0.0322(11) 0.0368(13) 0.0104(10) 0.0001(10) -0.0053(10) N16 0.0428(14) 0.0610(13) 0.0449(13) 0.0265(10) -0.0070(10) -0.0069(10) N17 0.0361(14) 0.0571(13) 0.0355(12) 0.0200(10) -0.0026(10) -0.0151(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 N1 C7A 1.320(3) . ? N1 N2 1.364(2) . ? N2 C3 1.355(3) . ? N2 H2 0.92(2) . ? C3 C3A 1.380(3) . ? C3 C14 1.488(3) . ? C3A C7A 1.382(3) . ? C3A C4 1.500(3) . ? C4 C8 1.526(3) . ? C4 C5 1.526(3) . ? C4 H4 0.9800 . ? C5 C6 1.354(3) . ? C5 C15 1.415(3) . ? C6 N17 1.348(3) . ? C6 O7 1.377(2) . ? O7 C7A 1.374(2) . ? C8 C13 1.382(3) . ? C8 C9 1.384(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9300 . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.372(3) . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N16 1.149(3) . ? N17 H171 0.89(3) . ? N17 H172 0.92(2) . ? 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 C7A N1 N2 101.42(17) . . ? C3 N2 N1 113.87(18) . . ? C3 N2 H2 127.8(16) . . ? N1 N2 H2 118.3(15) . . ? N2 C3 C3A 105.66(18) . . ? N2 C3 C14 122.21(19) . . ? C3A C3 C14 132.1(2) . . ? C3 C3A C7A 103.87(18) . . ? C3 C3A C4 132.80(19) . . ? C7A C3A C4 123.33(18) . . ? C3A C4 C8 112.18(15) . . ? C3A C4 C5 106.05(16) . . ? C8 C4 C5 112.05(16) . . ? C3A C4 H4 108.8 . . ? C8 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C6 C5 C15 116.96(18) . . ? C6 C5 C4 126.15(18) . . ? C15 C5 C4 116.88(18) . . ? N17 C6 C5 127.4(2) . . ? N17 C6 O7 108.99(19) . . ? C5 C6 O7 123.62(18) . . ? C7A O7 C6 114.57(17) . . ? N1 C7A O7 118.77(18) . . ? N1 C7A C3A 115.17(18) . . ? O7 C7A C3A 126.05(19) . . ? C13 C8 C9 118.09(19) . . ? C13 C8 C4 121.55(19) . . ? C9 C8 C4 120.3(2) . . ? C8 C9 C10 120.9(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 121.2(2) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C3 C14 H14A 109.5 . . ? C3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N16 C15 C5 178.9(2) . . ? C6 N17 H171 120.9(16) . . ? C6 N17 H172 121.9(14) . . ? H171 N17 H172 116(2) . . ? 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 C7A N1 N2 C3 -0.3(2) . . . . ? N1 N2 C3 C3A -0.1(2) . . . . ? N1 N2 C3 C14 179.74(18) . . . . ? N2 C3 C3A C7A 0.5(2) . . . . ? C14 C3 C3A C7A -179.4(2) . . . . ? N2 C3 C3A C4 -179.6(2) . . . . ? C14 C3 C3A C4 0.5(4) . . . . ? C3 C3A C4 C8 -60.4(3) . . . . ? C7A C3A C4 C8 119.5(2) . . . . ? C3 C3A C4 C5 177.0(2) . . . . ? C7A C3A C4 C5 -3.1(3) . . . . ? C3A C4 C5 C6 5.2(3) . . . . ? C8 C4 C5 C6 -117.6(2) . . . . ? C3A C4 C5 C15 -174.55(18) . . . . ? C8 C4 C5 C15 62.7(2) . . . . ? C15 C5 C6 N17 -4.9(3) . . . . ? C4 C5 C6 N17 175.4(2) . . . . ? C15 C5 C6 O7 176.31(18) . . . . ? C4 C5 C6 O7 -3.4(3) . . . . ? N17 C6 O7 C7A 179.87(17) . . . . ? C5 C6 O7 C7A -1.1(3) . . . . ? N2 N1 C7A O7 -179.32(17) . . . . ? N2 N1 C7A C3A 0.6(2) . . . . ? C6 O7 C7A N1 -176.90(18) . . . . ? C6 O7 C7A C3A 3.2(3) . . . . ? C3 C3A C7A N1 -0.7(2) . . . . ? C4 C3A C7A N1 179.32(18) . . . . ? C3 C3A C7A O7 179.20(19) . . . . ? C4 C3A C7A O7 -0.7(3) . . . . ? C3A C4 C8 C13 -72.2(2) . . . . ? C5 C4 C8 C13 47.0(3) . . . . ? C3A C4 C8 C9 106.9(2) . . . . ? C5 C4 C8 C9 -134.0(2) . . . . ? C13 C8 C9 C10 0.6(3) . . . . ? C4 C8 C9 C10 -178.52(18) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C9 C8 C13 C12 -0.7(3) . . . . ? C4 C8 C13 C12 178.39(18) . . . . ? C11 C12 C13 C8 0.5(3) . . . . ? C6 C5 C15 N16 152(14) . . . . ? C4 C5 C15 N16 -28(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.209 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.041