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The article presents a scientific report on the structure of the compounds 4-aminopyridinium 4-aminobenzoate dihydrate and 4-aminopyridinium nicotinate. It examines the hydrogen-bonding patterns of 4-aminopyridine with other substances, including carboxylic acids and the two 4-aminopyridinium compounds. The report mentions that the nicotinate compound yielded colorless crystals that are suitable for X-ray diffraction after two weeks.

The article presents information on the structure of the third form of vitamin B1, C12H18N4OS2+∙2Cl-&3x2219;H2O. Thiamine is a coenzyme in a number of important metabolic processes, such as the decarboxylation of α-keto acids and the transfer of aldehyde or acyl groups. In the study, the H atoms were located in a difference map, leading to a better understanding of the hydrogen-bonding pattern in vitamin B1. In the third form of vitamin B1 the planes of the pyrimidine and thiazolium rings are at a dihedral angle of 79 (15)°.

In the title compound, 2C7H7NO2·C6H5NO2, the 4-amino­benzoic acid and the nicotinic acid mol­ecules are approximately planar. The crystal structure is stabilized by an extensive network of N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds. [ABSTRACT FROM AUTHOR]

The title compound, C7H7NO3S, is a simple new pyridylthio- N-oxide of pharmacological inter­est. There are two independent mol­ecules in the asymmetric unit. Strong O—H⋯O hydrogen-bond inter­actions link the mol­ecules in ribbons lying in the (101) plane. [ABSTRACT FROM AUTHOR]

In the title compound, [Ag(NO3)(C15H18N6)], the AgI atom is four-coordinated by the three N atoms of the 2-aminopyridine ligands and by an O atom of the nitro group. The structure is stabilized by an extensive network of N—H—O and N—H—N hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound, C6H6NO2+·NO3−·H2O, the nicotinium cation is essentially planar. N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into layers parallel to the (10 ) plane. [ABSTRACT FROM AUTHOR]

In the crystal structure of the title compound, (C5H7N2)2[CoCl4], the CoII ion is coordinated by four chloride ions. The Co atom lies on a crystallographic twofold rotation axis. The structure is stabilized by an extensive network of N—H⋯Cl hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the structure of the title compound, 2C5H7N2+·SO42−, the S atom of the sulfate anion lies on a twofold axis. The structure is stabilized by an extensive network of N—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound, C5H7N2+·C7H4NO4−, the asymmetric unit consists of an aminopyridinium cation and a p-nitro­benzoate anion, with proton transfer occurring to the aromatic N atom of the 2-amino­pyridine molecule. In the crystal structure, the two ions are inter­connected by N—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound, [Mn(H2O)6](C7H6NO3S)2, the pyridylsulfanyl N-oxide acetate anions have no direct coordination to the MnII atom. The MnII atom is octa­hedrally coordinated by six water mol­ecules and is located on an inversion centre. The cations and anions are linked by O—H⋯O hydrogen bonds into a three-dimensional network. [ABSTRACT FROM AUTHOR]

In the title hydrate, C13H11N3O·H2O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methyl-ene group, forming a dihedral angle of 81.87 (15)°. In the crystal, mol-ecules are linked into chains along [001] by O-H⋯O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C-H⋯O, C-H⋯π and π-π [centroid-centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] inter-actions.

In the title compound, C(6)H(5)N(3)O·C(13)H(11)N(3)O, the benzo-triazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) mol-ecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hy-droxy-benzotriazole (B) mol-ecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C-H⋯O and C-H⋯π inter-actions are present. The A and B molecules are linked by an O-H⋯N hydrogen bond.

In the title compound, C(13)H(11)N(3)O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027 (16) Å] and the benzene ring is 10.28 (9)°. The C-C-O-N bond adopts an anti conformation [torsion angle = -177.11 (16)°]. In the crystal, the mol-ecules inter-act via weak C-H⋯π inter-actions and aromatic π-π stacking [centroid-to-centroid distance = 3.731 (12) Å].

In the title compound, [K(2)PtCl(4)(C(12)H(24)O(6))(2)], the Pt(II) ion is located on an inversion centre and is coordinated by four Cl atoms, forming a square-planar geometry. The K(I) ion is coordinated by six O atoms of the crown ether and two bridging Cl atoms. The K(I) ion is displaced by 0.756 (2) Å from the mean plane of the six O atoms of the crown ether. The mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming an infinite two-dimensional network parallel to the (10) plane. Intra- and inter-molecular C-H⋯Cl hydrogen bonds are also observed.

In the structure of the title compound, [KPt(C(6)H(4)N(3)O)Cl(2)(C(6)H(5)N(3)O)(C(12)H(24)O(6))], the Pt(II) atom is in a distorted square-planar geometry. The crystal structure is consolidated by O-H⋯O hydrogen bonds. The measured crystal was a non-merohedral twin with four components.

In the title compound, C(16)H(17)N(3)O, the benzotriazole ring forms a dihedral angle of 77.25 (6)° with the phenyl ring. The benzotriazole ring is essentially planar with a maximum deviation of 0.012 (19) Å. Weak inter-molecular C-H⋯O hydrogen bonds form R(2) (2)(10) motifs. The crystal packing is consolidated by π-π inter-actions with centroid-centroid distances of 3.5994 (12) Å together with very weak C-H⋯π inter-actions.

There are two monomeric units in the asymmetric unit of the polymeric title compound, [Na(C(5)H(4)NOS)(C(10)H(8)N(2)O(2)S(2))(H(2)O)](n). The Na(I) ions are six coordinated by four O atoms, one S atom and one water mol-ecule, forming a slightly distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond stabilizes the conformation of the mol-ecule. The crystal packing is consolidated by inter-molecular O-H⋯O, O-H⋯N and O-H⋯S hydrogen bonds, π-π inter-actions [with centroid-centroid distances of 3.587 (2) Å] together with weak C-H⋯π inter-actions. The mol-ecules are linked into polymeric chains along the b-axis direction.

The asymmetric unit of the title compound, C(11)H(12)N(2)O(4), contains 12 crystallographically independent mol-ecules, labelled A to L. The nitro and carboxyl groups are twisted slightly out of the plane of the attached benzene ring in all independent mol-ecules except mol-ecules G and D. The nitro group is coplanar with the benzene ring in mol-ecule G and the carboxyl group is coplanar with the benzene ring in mol-ecule D. The orientation of the butyl group with respect to the rest of the mol-ecule is different in some of the independent mol-ecules, with the C-C-C-C torsion angles varying from 104.2 (5) to 126.6 (7)°. In each independent mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the 12 independent mol-ecules exist as six pairs of O-H⋯O hydrogen-bonded R(2) (2)(8) dimers. In addition, C-H⋯O hydrogen bonds are observed.

The title compound, C(14)H(18)N(2)O(3), crystallizes with two independent mol-ecules in the asymmetric unit, having closely comparable geometries. Both mol-ecules are essentially planar [maximum deviations from the mean plane of 0.069 (1) and 0.068 (1) Å for the two mol-ecules] and contain an intra-molecular N-H⋯O hydrogen bond which generates a ring with graph-set motif S(6). In the crystal, the mol-ecules are linked into chains along the c axis by inter-molecular C-H⋯O hydrogen bonds, and inter-molecular C-H⋯π inter-actions are also present.

In the title mol-ecule, C(20)H(16)N(2)O(2), the benzimidazole mean plane forms dihedral angles of 56.55 (3) and 81.65 (4)° with the two benzene rings. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into layers parallel to the (101) plane. The crystal packing also exhibits weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

In the title mol-ecule, C(24)H(22)O(8), the mean planes of the two coumarin units are inclined to each other at a dihedral angle of 79.93 (3)°. The attached meth-oxy groups form torsion angles of 7.65 (19) and 78.36 (14)° with respect to one coumarin unit, and angles of 9.01 (16) and 99.08 (11)° with respect to the other coumarin unit. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect pairs of mol-ecules to form dimers, generating R(2) (2)(16) and R(2) (2)(18) rings; the dimers are linked by further weak inter-molecular C-H⋯O hydrogen bonds, forming extended chains. Additional stabil-ization is provided by weak C-H⋯π inter-actions.

In the title compound, C(21)H(23)BrN(4)S, the 4-bromo-benzyl-idene group is disordered over two orientations with occupancies of 0.504 (5) and 0.496 (5). One of the methyl groups of the isobutyl unit is disordered over two sites with occupancies of 0.751 (19) and 0.249 (19). The benzene rings of the isobutylphenyl and bromo-phenyl (major disorder component) groups form dihedral angles of 71.63 (11) and 21.8 (3)°, respectively, with the triazole ring. In the crystal, centrosymmetrically related mol-ecules exist as centrosymmetric N-H⋯S hydrogen-bonded dimers.

In the title compound, C(11)H(15)N(3)O(3), one of the methyl groups attached to the benzamide unit is slightly twisted with a C-N-C-C torsion angle of 4.04 (13)°. The crystal packing is stabilized by weak intermolecular C-H⋯O hydrogen bonds together with a weak C-H⋯π inter-action.

The asymmetric unit of the title compound, C(21)H(23)ClN(4)S, contains nine crystallographically independent mol-ecules, labelled A to I. The orientation of the 2-[4-(2-methyl-prop-yl)phen-yl]ethyl unit with respect to the rest of the mol-ecule is significantly different in mol-ecules E, F, H and I compared to the other independent mol-ecules. The isobutyl group of mol-ecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chloro-phenyl and methyl-propyl-phenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in mol-ecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent mol-ecule, a C-H⋯S hydrogen bond is observed. The crystal packing is stabilized by N-H⋯S and C-H⋯S hydrogen bonds, and by C-H⋯π inter-actions involving the methyl-propyl-phenyl ring.

In the title compound, C(11)H(14)N(2)O(4), all non-H atoms lie in a mirror plane except for one of the methyl groups which deviates from the mirror plane by 0.919 (3) Å and is twisted by a torsion angle of 62.9 (2)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal packing, the mol-ecules are linked together by O-H⋯O hydrogen bonds, forming dimers with graph-set motif R(2) (2)(8) which propagate along the a-axis direction. C-H⋯O contacts link adjacent dimers with a graph-set motif C(2) (2)(7), forming chains along b, and further consolidate the structure into a three-dimensional network. The crystal packing is further strengthened by short inter-molecular O⋯O=C [2.655 (4) Å] contacts.

In the title compound, C(22)H(21)ClO(4), the cyclo-hex-3-ene unit adopts an envelope conformation in both independent mol-ecules comprising the asymmetric unit. The two benzene rings are inclined to each other at a dihedral angle of 82.03 (5)° [86.37 (5)°]. In the crystal, the molecules interact via C-H⋯O, C-H⋯Cl and C-H⋯π interactions.

In the title compound, C(22)H(26)N(4)OS, the benzene rings of the (2-methyl-prop-yl)phenyl and 4-methoxy-phenyl units form dihedral angles of 66.85 (3) and 25.96 (3)°, respectively, with the triazole ring. The dihedral angle between the two benzene rings is 87.42 (2)°. The -CH(CH(3)) linkage is disordered over two orientations with occupancies of 0.907 (3) and 0.093 (3). An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. Inter-molecular N-H⋯S hydrogen bonds and C-H⋯π inter-actions are observed.

The asymmetric unit of the title compound, C(11)H(14)N(2)O(4), comprises four crystallographically independent mol-ecules (A, B, C and D) with similar geometries. In each mol-ecule, the butyl-amino side chain is in an extended conformation, and the carboxyl and butyl-amino groups are almost coplanar with the attached benzene ring; the nitro group is slightly twisted away from the benzene ring. In the asymmetric unit, the benzene rings of mol-ecules A, B and C are stacked parallel to one another, with a centroid-centroid distance of 3.6197 (11) or 3.6569 (11) Å, indicating π-π inter-actions. An intra-molecular N-H⋯O hydrogen bond is observed in each independent mol-ecule. In addition to the π-π inter-actions, the crystal packing is consolidated by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal studied was a non-merohedral twin. The minor twin component refined to a value of 0.290 (1).

In the title compound, (C(5)H(7)N(2))(2)[CoCl(4)], the cobalt(II) ion is coordinated by four chloride ions in a slightly distorted tetra-hedral geometry. The crystal packing is stabilized by inter-molecular N-H⋯Cl hydrogen bonding, forming a three-dimensional network. The crystal was a non-merohedral twin emulating tetra-gonal symmetry, but being in fact ortho-rhom-bic.

The asymmetric unit of the title compound, C(20)H(18)F(2)N(2)O(2)S, contains four independent mol-ecules, two of which are paired into a dimer by way of two N-H⋯S hydrogen bonds. The other two independent mol-ecules are paired into two centrosymmetric dimers via pairs of inter-molecular N-H⋯S hydrogen bonds. In one mol-ecule, the carboxyl-ate O atoms, methyl-ene and methyl groups attached to the benzene ring are disordered between two positions in a 0.908 (3):0.092 (3) ratio. In two of the independent mol-ecules, the F and H atoms of the diflourophenyl ring are flip-flop disordered (i.e. by 180° about the C-C bond axis linking the ring to the rest of the molecule) in a 3:2 ratio. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

In the title compound, C(10)H(18)O(5)·H(2)O, the fucopyran-oside ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds together with intra-molecular O⋯O [2.2936 (8) Å] and inter-molecular O⋯O [2.7140 (8)-2.829 (3) Å] short contacts. The mol-ecules are linked together to form an infinite chain along the a axis. This structure has been solved previously but with no R-values [Spiers (1931). Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem.78, 101].

In the centrosymmetric title compound, [Ni(C(8)H(8)NO(3)S)(2)(H(2)O)(4)], the Ni(II) ion, which lies on an inversion centre, is six coordinated by four water mol-ecules and two propionate O atoms from two 2-pyridylsulfanylpropionate N-oxide ligands, forming a slightly distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is consolidated by inter-molecular O-H⋯O and C-H⋯O hydrogen bonding.

In the title compound, C(20)H(16)S(2), the pyrene ring is planar [maximum deviation 0.0144 (15) Å] and the dithiane ring adopts a chair conformation. The crystal packing is stabilized by C-H⋯π inter-actions. An intra-molecular C-H⋯S hydrogen bond generates an S(5) ring motif.

In the title compound, C(17)H(19)N(3)O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4)° with the mean plane of the benzene ring. The crystal packing is stabilized by π-π stacking inter-actions, with a centroid-centroid distance of 3.8077 (12) Å, together with weak C-H⋯π inter-actions. Mol-ecules are stacked along the a axis.

The complete molecule of the title compound, C(24)H(24)N(6)O(2), is generated by a crystallographic inversion centre. The benzotriazole rings form dihedral angles of 2.10 (7)° with the central aromatic ring. The crystal packing is consolidated by π-π inter-actions, with centroid-centroid distances of 3.6234 (10) Å, together with weak C-H⋯π inter-actions.

The mol-ecule of the title compound, C(11)H(7)ClO(3), is planar, with a maximum deviation of 0.0383 (10) Å from the naphthoquinone plane. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds. Short intra-molecular Cl⋯O [2.8234 (8) Å] and O⋯O [2.5530 (11) Å], and inter-molecular Cl⋯Cl [3.2777 (3) Å] contacts further stabilize the crystal structure.

In the title compound, 2C(3)H(5)N(2)S(+)·C(4)H(4)O(4) (2-)·C(4)H(6)O(4), the thia-zolium ring is almost planar, with the maximum deviation from planarity being 0.0056 (8) Å for the C atom carrying the amine substituent. The N atom of the 2-amino-thia-zole mol-ecule is protonated. Both the anion and the acid lie across inversion centres. The crystal packing is consolidated by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. Mol-ecules are stacked down the b axis.

In the title salt, C(5)H(7)N(2) (+)·C(4)H(5)O(4) (-), the asymmetric unit comprises an amino-pyridinium cation and a hydrogen succinate anion as protonation of the aromatic N atom of the 4-amino-pyridine mol-ecule has occurred. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds that lead to a two-dimensional array. Short C-H⋯O contacts are also present.

In the title compound, 2C(5)H(7)N(2) (+)·2C(2)HO(4) (-)·H(2)O, the asymmetric unit consists of an amino-pyridinium cation, an oxalic actetate anion and a half-molecule of water, which lies on a two-fold rotation axis. The crystal packing is consolidated by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. The mol-ecules are linked into an infinite one dimensional chain along [010].

In the title compound, C(14)H(21)N(3)OS, inter-molecular N-H⋯O inter-actions generate ten-membered rings with R(2) (2)(10) ring motifs, whereas N-H⋯S inter-actions generate eight, 14- and 16-membered rings with R(2) (2)(8), R(4) (4)(14) and R(4) (4)(16) ring motifs, respectively. There are weak intra-molecular N-H⋯π inter-actions which might influence the conformation of the mol-ecule. The compound has a stereogenic center but the space group is centrosymmetic so the mol-ecule exists as a racemate.

In the title binuclear copper(II) complex, [Cu(2)(C(7)H(3)ClNO(4))(4)(H(2)O)(2)], each of the two independent Cu(II) center is five-coordinated by four O atoms of the carboxyl-ate groups in the basal plane and one O atom of a water mol-ecule in the apical position, in a distorted square-pyramidal geometry. The Cu-Cu distance is 2.6458 (4) Å. In the crystal structure, the dinuclear units are linked into a three-dimensional network by O-H⋯O, C-H⋯O and C-H⋯Cl hydrogen bonds. One of the Cl atoms is disordered over two positions with occupancies of 0.650 (2) and 0.350 (2).

In the crystal structure of the title compound, 4C(21)H(22)N(2)O(2)S(2)·0.5C(3)H(6)O·11.5H(2)O, there are four crystallographically independent mol-ecules (A, B, C, D) with similar geometries, 11 water mol-ecules and a solvent acetone mol-ecule which is disordered with a water mol-ecule with occupancy factors of 0.5:0.5. The dihedral angles formed by the mesitylene ring with the two pyridyl rings are 82.07 (3) and 78.39 (3)° in mol-ecule A, 86.20 (3) and 82.29 (3)° in mol-ecule B, 81.05 (3) and 76.0 (4)° in mol-ecule C, 86.0 (3) and 80.9 (3)° in moleule D. The two pyridyl rings form dihedral angles of 41.17 (4), 64.01 (3), 81.9 (3) and 82.25 (3)° in mol-ecules A, B, C and D, respectively. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds and possible weak C-H⋯π inter-actions. Some short intra-molecular S⋯O contacts are apparent [2.684 (4)-2.702 (4) Å].

In the title compound, C(17)H(14)ClN(5)OS, the dihedral angles formed by the two benzene rings with the triazole ring are 66.88 (3) and 19.16 (3)°, and the benzene rings are inclined to each other with a dihedral angle of 78.40 (3)°. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the (100) planes, and centrosymmetric π-π stacking inter-actions [centroid-centroid distance = 3.7717 (5) Å] are formed between benzene rings in neighbouring layers.

The asymmetric unit of the title compound, C(21)H(25)ClN(2)O, contains four crystallographically independent mol-ecules, which differ mainly in the orientation of the isobutyl groups. The benzene rings are almost orthogonal to each other, forming dihedral angles of 87.40 (6), 88.69 (6), 84.88 (6) and 85.12 (6)° in the four mol-ecules. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, together with C-H⋯π inter-actions.

In the racemic (S,S/R,R) title compound, C(19)H(21)BrO(4), the two benzene rings are almost coplanar to each other, forming a dihedral angle of 3.58 (10)°. The crystal packing is strengthened by inter-molecular Br-O [2.9800 (16) Å] short contacts, which link the molecules into infinite one-dimensional chains along [001].

The asymmetric unit of the title compound, C(22)H(22)O(4), consists of two independent mol-ecules (A and B) which differ significantly in the orientations of ethyl carboxyl-ate groups. The phenyl ring in mol-ecule B is disordered over two orientations with occupancies of 0.55 (2) and 0.45 (2). The cyclo-hexenone ring of both mol-ecules adopts an envelope conformation. The dihedral angle between the two aromatic rings is 81.12 (7)° in mol-ecule A and 70.8 (3)° in mol-ecule B [57.5 (4)° in the minor disorder component]. The crystal structure is stabilized by weak intermolecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

In the title compound, C(21)H(26)N(2)O, the dihedral angle between the two aromatic rings is 85.90 (19)°. The propenone-hydrazide unit forms dihedral angles of 21.62 (8) and 72.83 (9)°, respectively, with the terminal and central aromatic rings. The 2-methyl-propyl group is disordered over two sites, with occupancies of 0.533 (13) and 0.467 (13). In crystal structure, mol-ecules are linked into centrosymmetric dimers by paired N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π inter-actions are observed.

The chemical name in the title and the scheme of the paper by Fun, Jebas, Patil, Karthikeyan & Dharmaprakash [Acta Cryst. (2008), E64, o1559] are corrected.[This corrects the article DOI: 10.1107/S1600536808022289.].

In the title compound, C(22)H(26)N(4)S, the dihedral angles formed by the triazole ring with the two benzene rings are 87.51 (3) and 20.98 (3)°. The benzene rings are inclined at 71.88 (2)°. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. The crystal packing is strengthened by inter-molecular N-H⋯S hydrogen bonding and π-π stacking inter-actions between the triazole and benzene rings, with a centroid-centroid distance of 3.6618 (5) Å, together with N⋯N [2.1299 (9)-2.2121 (9) Å] short contacts and C-H⋯π inter-actions. In the crystal packing, mol-ecules are stacked along the a axis.

In the title compound, C(21)H(16)ClN(3)O(2), the dihedral angles formed by the pyrazole ring with the pyridyl, phenyl-ene and phenyl rings are 6.80 (5), 9.23 (5) and 74.96 (5)°, respectively. The phenyl and phenyl-ene rings are inclined at 80.14 (2)°. Intra-molecular O-H⋯O and C-H⋯N hydrogen bonds generate S(6) ring motifs. The crystal packing is strengthened by short inter-molecular O-H⋯N, C-H⋯O hydrogen bonds and π-π stacking inter-actions with centroid-centroid distances of 3.6247 (5)-3.7205 (5) Å, together with inter-molecular short O⋯N contacts [2.7682 (11) Å]. Mol-ecules are linked into infinite chains along [100].