data_a_3-APH+.3-F-4-HBA-_1:1_(6) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Aminopyridinium 3-flouro-4-hydroxybenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C7H4O3F.C5H7N2 _chemical_formula_sum 'C12 H11 F N2 O3' _chemical_formula_weight 250.23 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0905(16) _cell_length_b 9.0847(12) _cell_length_c 12.0905(16) _cell_angle_alpha 90.00 _cell_angle_beta 118.30 _cell_angle_gamma 90.00 _cell_volume 1169.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2106 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 25.92 _exptl_crystal_description 'block' _exptl_crystal_colour brown _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 4916 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2032 _reflns_number_gt 1687 _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^)+(0.0712P)^2^+0.2033P] 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 2032 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.72696(10) 1.14847(14) 0.18086(11) 0.0515(4) Uani 1 1 d . . . C6 C 1.00253(16) 0.84607(19) 0.20564(16) 0.0439(4) Uani 1 1 d . . . C5 C 1.00241(15) 0.79943(18) 0.09659(16) 0.0423(4) Uani 1 1 d . . . C3 C 0.81509(17) 0.9442(2) -0.02316(16) 0.0476(4) Uani 1 1 d . . . O2 O 0.62589(12) 1.12372(16) -0.02504(12) 0.0634(4) Uani 1 1 d . . . C2 C 0.81663(14) 0.99255(18) 0.08658(15) 0.0399(4) Uani 1 1 d . . . O3 O 1.08924(13) 0.70827(15) 0.09380(13) 0.0561(4) Uani 1 1 d . . . F1 F 0.90414(12) 0.80335(16) -0.12280(10) 0.0822(5) Uani 1 1 d . . . C1 C 0.71740(15) 1.09489(18) 0.08075(16) 0.0435(4) Uani 1 1 d . . . C7 C 0.91090(16) 0.94167(19) 0.20004(16) 0.0437(4) Uani 1 1 d . . . C4 C 0.90587(17) 0.8498(2) -0.01632(15) 0.0475(4) Uani 1 1 d . . . N1 N 0.46142(14) 0.29438(16) -0.00117(14) 0.0487(4) Uani 1 1 d . . . C8 C 0.49109(17) 0.3538(2) 0.10985(18) 0.0481(4) Uani 1 1 d . . . C10 C 0.29259(17) 0.4718(2) 0.01974(18) 0.0518(5) Uani 1 1 d . . . C9 C 0.40810(16) 0.4451(2) 0.12574(16) 0.0481(4) Uani 1 1 d . . . C12 C 0.35057(18) 0.3180(2) -0.10278(19) 0.0541(5) Uani 1 1 d . . . N2 N 0.4416(2) 0.5076(3) 0.23889(18) 0.0770(6) Uani 1 1 d . . . C11 C 0.26504(17) 0.4081(2) -0.09305(18) 0.0544(5) Uani 1 1 d . . . H6 H 1.0747(12) 0.8112(14) 0.2932(13) 0.019(3) Uiso 1 1 d . . . H7 H 0.9113(16) 0.9711(18) 0.2714(17) 0.042(5) Uiso 1 1 d . . . H8 H 0.5695(18) 0.332(2) 0.1738(18) 0.054(5) Uiso 1 1 d . . . H2B H 0.386(2) 0.551(2) 0.251(2) 0.064(6) Uiso 1 1 d . . . H11 H 0.183(2) 0.428(2) -0.167(2) 0.064(6) Uiso 1 1 d . . . H12 H 0.3389(18) 0.271(2) -0.178(2) 0.057(5) Uiso 1 1 d . . . H3A H 1.146(2) 0.688(2) 0.171(2) 0.074(7) Uiso 1 1 d . . . H3 H 0.747(2) 0.977(2) -0.099(2) 0.074(6) Uiso 1 1 d . . . H10 H 0.2372(18) 0.534(2) 0.0292(17) 0.053(5) Uiso 1 1 d . . . H1 H 0.518(2) 0.232(2) -0.012(2) 0.074(6) Uiso 1 1 d . . . H2A H 0.508(2) 0.473(3) 0.305(2) 0.085(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 O1 0.0382(7) 0.0664(8) 0.0473(7) -0.0108(6) 0.0182(6) 0.0015(5) C6 0.0400(9) 0.0492(9) 0.0366(9) 0.0033(7) 0.0134(7) 0.0027(7) C5 0.0390(9) 0.0441(9) 0.0442(10) 0.0043(7) 0.0202(8) 0.0023(7) C3 0.0431(10) 0.0576(11) 0.0363(9) 0.0048(8) 0.0141(8) 0.0069(8) O2 0.0457(7) 0.0807(10) 0.0470(8) -0.0098(7) 0.0081(6) 0.0191(6) C2 0.0334(8) 0.0436(9) 0.0406(9) -0.0010(7) 0.0157(7) -0.0025(7) O3 0.0537(8) 0.0661(9) 0.0494(8) 0.0079(6) 0.0253(7) 0.0207(6) F1 0.0899(9) 0.1135(11) 0.0412(7) 0.0038(6) 0.0296(6) 0.0416(8) C1 0.0343(9) 0.0477(10) 0.0437(10) -0.0038(7) 0.0146(8) -0.0033(7) C7 0.0440(10) 0.0498(10) 0.0359(9) -0.0025(7) 0.0178(8) -0.0009(7) C4 0.0510(10) 0.0586(11) 0.0335(9) 0.0002(8) 0.0206(8) 0.0062(8) N1 0.0421(8) 0.0503(9) 0.0510(9) -0.0027(7) 0.0200(7) 0.0036(6) C8 0.0397(10) 0.0526(10) 0.0450(10) 0.0037(8) 0.0144(8) 0.0051(8) C10 0.0426(10) 0.0578(11) 0.0533(11) 0.0038(9) 0.0212(9) 0.0102(8) C9 0.0464(10) 0.0530(10) 0.0429(10) 0.0034(8) 0.0197(8) 0.0061(8) C12 0.0492(11) 0.0588(11) 0.0471(11) -0.0056(9) 0.0170(9) 0.0009(8) N2 0.0684(13) 0.1054(15) 0.0455(11) -0.0037(10) 0.0175(10) 0.0353(12) C11 0.0393(10) 0.0620(12) 0.0490(11) 0.0005(9) 0.0102(8) 0.0044(8) _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 C1 1.258(2) . ? C6 C7 1.384(2) . ? C6 C5 1.384(2) . ? C6 H6 1.052(13) . ? C5 O3 1.3500(19) . ? C5 C4 1.387(2) . ? C3 C4 1.364(3) . ? C3 C2 1.389(2) . ? C3 H3 0.95(2) . ? O2 C1 1.260(2) . ? C2 C7 1.383(2) . ? C2 C1 1.493(2) . ? O3 H3A 0.88(3) . ? F1 C4 1.346(2) . ? C7 H7 0.901(18) . ? N1 C8 1.329(2) . ? N1 C12 1.338(2) . ? N1 H1 0.95(2) . ? C8 C9 1.383(2) . ? C8 H8 0.918(19) . ? C10 C11 1.369(3) . ? C10 C9 1.398(3) . ? C10 H10 0.925(19) . ? C9 N2 1.354(3) . ? C12 C11 1.367(3) . ? C12 H12 0.95(2) . ? N2 H2B 0.85(2) . ? N2 H2A 0.88(3) . ? C11 H11 0.98(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 C7 C6 C5 120.42(15) . . ? C7 C6 H6 120.0(7) . . ? C5 C6 H6 119.5(7) . . ? O3 C5 C6 124.19(15) . . ? O3 C5 C4 118.64(15) . . ? C6 C5 C4 117.16(15) . . ? C4 C3 C2 119.66(16) . . ? C4 C3 H3 124.0(13) . . ? C2 C3 H3 116.3(13) . . ? C7 C2 C3 118.24(15) . . ? C7 C2 C1 121.40(15) . . ? C3 C2 C1 120.35(15) . . ? C5 O3 H3A 109.4(15) . . ? O1 C1 O2 122.16(15) . . ? O1 C1 C2 119.37(14) . . ? O2 C1 C2 118.47(15) . . ? C2 C7 C6 121.50(16) . . ? C2 C7 H7 118.6(11) . . ? C6 C7 H7 119.9(11) . . ? F1 C4 C3 119.49(15) . . ? F1 C4 C5 117.51(15) . . ? C3 C4 C5 123.00(16) . . ? C8 N1 C12 122.39(17) . . ? C8 N1 H1 121.2(13) . . ? C12 N1 H1 116.4(13) . . ? N1 C8 C9 121.17(17) . . ? N1 C8 H8 116.0(12) . . ? C9 C8 H8 122.8(12) . . ? C11 C10 C9 120.35(18) . . ? C11 C10 H10 122.3(12) . . ? C9 C10 H10 117.4(12) . . ? N2 C9 C8 120.18(17) . . ? N2 C9 C10 122.94(18) . . ? C8 C9 C10 116.85(17) . . ? N1 C12 C11 119.09(18) . . ? N1 C12 H12 115.7(12) . . ? C11 C12 H12 125.2(12) . . ? C9 N2 H2B 119.4(15) . . ? C9 N2 H2A 118.6(16) . . ? H2B N2 H2A 117(2) . . ? C12 C11 C10 120.14(17) . . ? C12 C11 H11 120.4(12) . . ? C10 C11 H11 119.5(12) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.203 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.057