In the title compound, C(6)H(9)N(2) (+)·C(7)H(6)NO(2) (-), the H atom of the N-H group and an H atom of the 2-amino group from the cation are involved in inter-molecular N-H⋯O hydrogen bonds with the O atoms of the carboxyl-ate group of the anion, forming an R(2) (2)(8) ring motif. These ring motifs are, in turn, connected by further N-H⋯O hydrogen bonds, forming a two-dimensional network. The crystal structure is further stabilized by π⋯π stacking inter-actions involving the benzene and pyridinium rings with a centroid-centroid distance of 3.7594 (8) Å.
In the title compound, C(6)H(9)N(2) (+)·C(7)H(4)NO(4) (-), the nitro group of the 4-nitro-benzoate anion is twisted by 6.2 (2)° from the attached ring. In the crystal structure, the cations and anions are linked via strong N-H⋯O and weak C-H⋯O hydrogen bonds, forming a three-dimensional network.
The asymmetric unit of the title compound, C(5)H(7)N(2) (+)·C(2)F(3)O(2) (-), contains four independent 2-amino-pyridinium cations and four independent trifluoro-acetate anions. In the crystal structure, these ions are linked by N-H⋯O hydrogen bonds, forming four cation-anion pairs each containing an R(2) (2)(8) ring motif. The ion pairs are linked into two independent chains along [100] by N-H⋯O hydrogen bonds. In addition, C-H⋯O and C-H⋯F hydrogen bonds and π⋯π inter-actions [centoid-centroid separation = 3.6007 (17) Å] are observed.
In the title compound, C(5)H(6)BrN(2) (+)·C(4)H(5)O(4) (-), the pyridine N atom of the 2-amino-5-bromo-pyridine mol-ecule is protonated. The protonated N atom and the amino group are linked via N-H⋯O hydrogen bonds to the carboxyl-ate O atoms of the singly deprotonated succinate anion. The hydrogen succinate anions are linked via O-H⋯O hydrogen bonds. A weak inter-molecular C-H⋯O hydrogen bond is also observed.
In the title salt, C(5)H(6)BrN(2) (+)·C(7)H(6)NO(2) (-), the pyridine N atom of the 2-amino-5-bromo-pyridine mol-ecule is protonated. In the crystal, the protonated N atom and the 2-amino group are hydrogen-bonded to the carboxyl-ate O atoms via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. Two inversion-related 3-amino-benzoate anions are linked through N-H⋯O hydrogen-bonds, forming an R(2) (2)(14) ring motif. The crystal structure is further stabilized by π⋯π inter-actions involving the benzene and pyridinium rings with a centroid-centroid distance of 3.7743 (15) Å.
In the title adduct, C(5)H(5)BrN(2)·C(7)H(6)O(2), the carboxyl group of the benzoic acid mol-ecule is twisted away from the attached ring by 12.97 (11)°. The 2-amino-5-bromo-pyridine mol-ecules inter-act with the carboxylic group of neighbouring benzoic acid mol-ecules through N-H⋯O and O-H⋯N hydrogen bonds, forming cyclic R(2) (2)(8) hydrogen-bonded motifs and linking the mol-ecules into a two-dimensional network lying parallel to (100). The crystal structure is further stabilized by weak C-H⋯O hydrogen bonds.
In the title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(2) (-), the 2-amino-5-methyl-pyridinium cation is essentially planar, with a maximum deviation of 0.023 (2) Å. In the crystal, the cations and anions are linked via strong N-H⋯O hydrogen bonds, forming a two dimensional network parallel to (100). In addition, π⋯π inter-actions involving the pyridinium and pyridine rings, with centroid-centroid distances of 3.6383 (8) Å, are observed.
In the crystal structure of the title compound, C(5)H(9)N(3) (2+)·2NO(3) (-), the cations and anions are connected by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by π⋯π inter-actions between pyridinium rings [centroid-centroid distance = 3.775 (4) Å].
In the crystal structure of the title salt, C(5)H(6)BrN(2) (+)·C(6)H(4)NO(3) (-)·H(2)O, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ion pairs are further connected via O-H⋯O, N-H⋯O, N-H⋯Br and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The water mol-ecules self-assemble through O-H⋯O hydrogen bonds, forming one-dimensional supra-molecular chains along the a axis, with graph-set notation C(2) (2)(4).
In the title salt, C(6)H(9)N(2) (+)·C(8)H(5)O(4) (-), the hydrogen phthalate anion is essentially planar, with a maximum deviation of 0.011 (2) Å. In the crystal structure, the protonated N atom of the pyridine ring and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. In the hydrogen phthalate anion, there is a very strong, almost symmetric, intra-molecular O-H⋯O hydrogen bond, generating an S(7) motif [O⋯O = 2.382 (3) Å]. Furthermore, these two molecular motif rings are connected by a bifurcated N-H⋯(O,O) hydrogen-bonded motif R(1) (2)(4), forming a supra-molecular ribbon along the b axis. The crystal structure is further stabilized by π-π inter-actions between the cations and anions [centroid-centroid distance = 3.6999 (10) Å].
In the title salt, C(5)H(6)BrN(2) (+)·C(4)H(3)O(4) (-), the 2-amino-5-bromo-pyridinium cation and hydrogen maleate anion are planar, with maximum deviations from their mean planes of 0.016 (1) and 0.039 (1) Å, respectively. An intra-molecular O-H⋯O hydrogen bond generates an S(7) ring motif in the anion. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen-bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The motifs are linked into a two-dimensional network parallel to (011) by N-H⋯O and C-H⋯O hydrogen bonds.
In the title mol-ecular salt, C(6)H(9)N(2) (+)·C(3)H(3)O(4) (-), the cation is essentially planar, with a maximum deviation of 0.010 (3) Å. In the anion, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring and results in a folded conformation. In the crystal, the protonated NH group and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. Weak inter-molecular C-H⋯O inter-actions help to further stabilize the crystal structure.
The asymmetric unit of the title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(2) (-)·0.63H(2)O, contains two crystallographically independent 2-amino-5-methyl-pyridinium cations, a pair of picolinate anions and two water mol-ecules, one with an occupancy of 0.25. Both the 2-amino-5-methyl-pyridine mol-ecules are protonated at the pyridine N atoms. In the crystal structure, the cations, anions and water mol-ecules are linked via N-H⋯O, N-H⋯N and O-H⋯O hydrogen bonds, as well as by C-H⋯O contacts, forming a chain along the b axis. In addition, weak π-π inter-actions are observed between pyridinium rings, with centroid-centroid distances of 3.5306 (13) Å.
In the title mol-ecular salt, C(6)H(9)N(2) (+)·C(7)H(3)N(2)O(7) (-), the 2-amino-5-methyl-pyridinium cation is essentially planar, with a maximum deviation of 0.023 (1) Å. There is an intra-molecular O-H⋯O hydrogen bond in the 3,5-dinitro-salicylate anion, which generates an S(6) ring motif. In the crystal, the protonated N atom and the 2-amino group are hydrogen bonded to the carboxyl-ate O atoms via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. Weak inter-molecular C-H⋯O inter-actions help to further stabilize the crystal structure.
The asymmetric unit of the title compound, C(2)H(2)N(4)O(2), contains two crystallographically independent mol-ecules in which the triazole rings are essentially planar, with maximum deviations of 0.003 (1) Å in both molecules. The dihedral angle between the two 1H-1,2,4-triazole rings is 56.58 (5)°. In the crystal, mol-ecules are linked via inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a supra-molecular chain along the b axis.
The asymmetric unit of the title compound, C(5)H(5)ClN(2)·0.5C(4)H(4)O(4), comprises a neutral 2-amino-5-chloro-pyridine mol-ecule and one half of a fumaric acid mol-ecule which lies on an inversion center. The dihedral angle between the pyridine ring and the plane formed by the fumaric acid mol-ecule is 3.22 (8)°. The 2-amino-5-chloro-pyridine mol-ecule is planar, with a maximum deviation of 0.004 (1) Å for the pyridine N atom. In the crystal, the 2-amino-5-chloro-pyridine mol-ecules inter-act with the carboxyl groups of fumaric acid mol-ecules through N-H⋯O and O-H⋯N hydrogen bonds, forming centrosymmetric R(2) (2)(8) ring motifs and another N-H⋯O hydrogen bond links these motifs into a two-dimensional network parallel to (100).
The asymmetric unit of the title mol-ecular salt, C(6)H(9)N(2) (+)·C(7)H(5)O(3) (-), contains two cations and two anions. Both the salicylate anions contain an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. Both the 2-amino-4-methyl-pyridine mol-ecules are protonated at their pyridine N atoms. In the crystal, both cations form two N-H⋯O hydrogen bonds to their adjacent anions, forming ion pairs. Further N-H⋯O links generate sheets lying parallel to the ab plane. In addition, weak C-H⋯O bonds and aromatic π-π stacking inter-actions [centroid-centroid distances = 3.5691 (9) and 3.6215 (9) Å] are observed between the cations and anions.
In the title salt, C(5)H(6)ClN(2) (+)·C(5)H(7)O(4) (-), the 2-amino-5-chloro-pyridinium cation is essentially planar, with a maximum deviation of 0.010 (3) Å. In the crystal structure, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ion pairs are further connected via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming a layer parallel to the bc plane. In the layer, the hydrogen glutarate anions self-assemble via O-H⋯O hydrogen bonds, forming a supra-molecular chain along the c axis. Furthermore, the cations and anions are stacked down along the a axis, forming a three-dimensional network.
The title compound, C(7)H(10)N(2)O(2)S, is essentially planar [maximum deviation 0.018 (4) Å]. In the crystal, mol-ecules are linked into chains by C-H⋯N hydrogen bonds and the chains are arranged in layers parallel to the ab plane.
In the title compound, C(5)H(8)N(3) (+)·C(7)H(4)NO(4) (-)·C(7)H(5)NO(4), the non-H atoms of the 3,4-diamino-pyridinium cation are coplanar, with a maximum deviation of 0.022 (1) Å. The carboxyl-ate and nitro groups of the 4-nitro-benzoate anion are twisted out of the attached ring planes by dihedral angles of 15.89 (8) and 10.20 (8)°, respectively. In the 4-nitro-benzoic acid mol-ecule, the carboxyl and nitro groups form dihedral angles of 18.25 (8) and 6.55 (8)°, respectively, with the benzene ring. In the crystal, the constituent units form two-dimensional networks parallel to (001) by O-H⋯O, N--H⋯O and C-H⋯O hydrogen bonds. Weak π-π inter-actions involving inversion-related 4-nitro-benzoic acid mol-ecules [centroid-centroid distance = 3.7325 (8) Å] and inversion-related 4-nitro-benzoate mol-ecules [centroid-centroid distance = 3.7124 (8) Å] are also observed.