The title homoleptic Schiff base complexes, [M(C14H9Cl2N2O)2], for M = CoII, (I), and CuII, (II), present distinct coordination geometries despite the Schiff base dianion coordinating via the phenolato-O and imine-N atoms in each case. For (I), the coordination geometry is based on a trigonal bipyramid whereas for (II), a square-planar geometry is found (Cu site symmetry overline{1}). In the crystal of (I), discernible supra­molecular layers in the ac plane are sustained by chloro­benzene-C—H⋯O(coordinated), chloro­benzene-C—H⋯π(fused-benzene ring) as well as π(fused-benzene, chloro­benzene)–π(chloro­benzene) inter­actions [inter-centroid separations = 3.6460 (17) and 3.6580 (16) Å, respectively]. The layers inter-digitate along the b-axis direction and are linked by di­chloro­benzene-C—H⋯π(fused-benzene ring) and π–π inter­actions between fused-benzene rings and between chloro­benzene rings [inter-centroid separations = 3.6916 (16) and 3.7968 (19) Å, respectively] . Flat, supra­molecular layers are also found in the crystal of (II), being stabilized by π–π inter­actions formed between fused-benzene rings and between chloro­benzene rings [inter-centroid separations = 3.8889 (15) and 3.8889 (15) Å, respectively]; these stack parallel to [10overline{1}] without directional inter­actions between them. The analysis of the respective calculated Hirshfeld surfaces indicate diminished roles for H⋯H contacts [26.2% (I) and 30.5% (II)] owing to significant contributions by Cl⋯H/H⋯Cl contacts [25.8% (I) and 24.9% (II)]. Minor contributions by Cl⋯Cl [2.2%] and Cu⋯Cl [1.9%] contacts are indicated in the crystals of (I) and (II), respectively. The inter­action energies largely arise from dispersion terms; the aforementioned Cu⋯Cl contact in (II) gives rise to the most stabilizing inter­action in the crystal of (II).

The title compound [systematic name: (1R*, 8S)-2-acetamidoocta­hydro­pyrrol­izin-4-ium chloride–N-[(1R, 8S)-hexa­hydro-1H-pyrrolizin-2-yl)acetamide (1/1)], 2(C9H16N2O)·HCl or C9H17N2O+·Cl−·C9H16N2O, arose as an unexpected product when 1-exo-acetamido­pyrrolizidine (AcAP; C9H16N2O) was dissolved in CHCl3. Within the AcAP pyrrolizidine group, the unsubstituted five-membered ring is disordered over two orientations in a 0.897 (5):0.103 (5) ratio. Two AcAP mol­ecules related by a crystallographic twofold axis link to H+ and Cl− ions lying on the rotation axis, thereby forming N—H⋯N and N—H⋯Cl⋯H—N hydrogen bonds. The first of these has an unusually short N⋯N separation of 2.616 (2) Å: refinement of different models against the present data set could not distinguish between a symmetrical hydrogen bond (H atom lying on the twofold axis and equidistant from the N atoms) or static or dynamic disorder models (i.e. N—H⋯N + N⋯H—N). Computational studies suggest that the disorder model is slightly more stable, but the energy difference is very small.

In 2,2,5-trimethyl-1,3-dioxane-5-carb­oxy­lic acid, C8H14O4, the carboxyl group occupies an equatorial position on the 1,3-dioxane ring. In the crystal, O—H⋯O hydrogen bonds form chains of mol­ecules, which are linked into a three-dimensional network by C—H⋯O hydrogen bonds. The asymmetric unit of 2,2,5-trimethyl-1,3-dioxane-5-carb­oxy­lic anhydride, C16H26O7, consists of two independent mol­ecules, which are linked by C—H⋯O hydrogen bonds. In the crystal, these units are connected into corrugated layers two mol­ecules thick and parallel to the ab plane by additional C—H⋯O hydrogen bonds.

The solvated title salt, [Ir(C9H7N2)2(C8H6N2)]PF6·CH2Cl2, was obtained from the reaction between 1,8-naphthyridine (NAP) and an orthometalated iridium(III) precursor containing a 1-phenyl­pyrazole (ppz) ligand. The asymmetric unit comprises one [Ir(ppz)2(NAP)]+ cation, one PF6− counter-ion and one CH2Cl2 solvent mol­ecule. The central IrIII atom of the [Ir(ppz)2(NAP)]+ cation is distorted-octa­hedrally coordinated by four N atoms and two C atoms, whereby two N atoms stem from the NAP ligand while the ppz ligands ligate through one N and one C atom each. In the crystal, the [Ir(ppz)2(NAP)]+ cations and PF6− counter-ions are connected with each other through weak inter­molecular C—H⋯F hydrogen bonds. Together with an additional C—H⋯F inter­action involving the solvent mol­ecule, a three-dimensional network structure is formed.

The mol­ecule of the title compound, C28H22N4O9, exhibits crystallographically imposed twofold rotational symmetry, with a dihedral angle of 66.0 (2)° between the planes of the two central benzene rings bounded to the central oxygen atom. The dihedral angle between the planes of the central benzene ring and the terminal phenol ring is 4.9 (2)°. Each half of the mol­ecule exhibits an imine E configuration. An intra­molecular O—H⋯N hydrogen bond is present. In the crystal, the mol­ecules are linked into layers parallel to the ab plane via C—H⋯O hydrogen bonds. The crystal studied was refined as a two-component pseudomerohedral twin.

The crystal and mol­ecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide mol­ecule has a (+)-anti­periplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 Å). The benzoic acid mol­ecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)°]. The formation of hy­droxy-O—H⋯N(pyrid­yl) hydrogen bonds between the benzoic acid mol­ecules and the pyridyl residues of the di­amide leads to a three-mol­ecule aggregate. Centrosymmetrically related aggregates assemble into a six-mol­ecule aggregate via amide-N—H⋯O(amide) hydrogen bonds through a 10-membered {⋯HNC2O}2 synthon. These are linked into a supra­molecular tape via amide-N—H⋯O(carbon­yl) hydrogen bonds and 22-membered {⋯HOCO⋯NC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methyl­ene-C—H⋯O(amide) and pyridyl-C—H⋯O(carbon­yl). These inter­actions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces.

The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thio­semicarbazide yielded the title compound, C11H17N3OS [common name: (R)- and (S)-camphor thio­semicarbazone], which maintains the chirality of the methyl­ated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c. There are two mol­ecules in general positions in the asymmetric unit, one of them being the (1R)-camphor thio­semicarbazone isomer and the second the (1S)- isomer. In the crystal, the mol­ecular units are linked by C—H⋯S, N—H⋯O and N—H⋯S inter­actions, building a tape-like structure parallel to the (overline{1}01) plane, generating R21(7) and R22(8) graph-set motifs for the H⋯S inter­actions. The Hirshfeld surface analysis indicates that the major contributions for crystal cohesion are from H⋯H (55.00%), H⋯S (22.00%), H⋯N (8.90%) and H⋯O (8.40%) inter­actions.

In the title compound, C18H15ClN2O·H2O, a benzohydrazide derivative, the dihedral angle between the mean plane of the di­hydro­naphthalene ring system and the phenyl ring is 17.1 (2)°. In the crystal, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the benzohydrazide and water mol­ecules, forming a layer parallel to the bc plane. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (45.7%) and H⋯C/C⋯H (20.2%) contacts.

The reaction of N-phenyl-1-(pyridin-2-yl)methanimine with copper chloride dihydrate produced the title neutral complex, [CuCl2(C12H10N2)(H2O)]·H2O. The CuII ion is five-coordinated in a distorted square-pyramidal geometry, in which the two N atoms of the bidentate Schiff base, as well as one chloro and a water mol­ecule, form the irregular base of the pyramidal structure. Meanwhile, the apical chloride ligand inter­acts through a strong hydrogen bond with a water mol­ecule of crystallization. In the crystal, mol­ecules are arranged in pairs, forming a stacking of symmetrical cyclic dimers that inter­act in turn through strong hydrogen bonds between the chloride ligands and both the coordinated and the crystallization water mol­ecules. The mol­ecular and electronic structures of the complex were also studied in detail using EPR (continuous and pulsed), FT–IR and Raman spectroscopy, as well as magnetization measurements. Likewise, Hirshfeld surface analysis was used to investigate the inter­molecular inter­actions in the crystal packing.

Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethyl­ene glycol in daylight afforded [3,4-bis­(phenyl­ethyn­yl)cyclo­butane-1,2-di­yl)bis­(pyridin-2-yl­methanone], C32H22N2O2 (3), while (E)-5-(4-methyl­phen­yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C17H13NO (2), remained photoinert. This is the first experimental evidence that pentenynones can be photoreactive when fixed in nearly coplanar parallel positions. During the photoreaction, the bond lengths and angles along the pentenyne chain changed significantly, while the disposition of the pyridyl ring towards the keto group was almost unchanged. The cyclo­butane ring adopts an rctt conformation.

The structure of the title quinoline carboxamide derivative, C26H25N3O, is described. The quinoline moiety is not planar as a result of a slight puckering of the pyridine ring. The secondary amine has a slightly pyramidal geometry, certainly not planar. Both intra- and inter­molecular hydrogen bonds are present. Hirshfeld surface analysis and lattice energies were used to investigate the inter­molecular inter­actions.

The title hydrazine carbodi­thio­ate, C13H18N2OS2, is constructed about a central and almost planar C2N2S2 chromophore (r.m.s. deviation = 0.0263 Å); the terminal meth­oxy­benzene group is close to coplanar with this plane [dihedral angle = 3.92 (11)°]. The n-butyl group has an extended all-trans conformation [torsion angles S—Cm—Cm—Cm = −173.2 (3)° and Cm—Cm—Cm—Cme = 180.0 (4)°; m = methyl­ene and me = meth­yl]. The most prominent feature of the mol­ecular packing is the formation of centrosymmetric eight-membered {⋯HNCS}2 synthons, as a result of thio­amide-N—H⋯S(thio­amide) hydrogen bonds; these are linked via meth­oxy-C–H⋯π(meth­oxy­benzene) inter­actions to form a linear supra­molecular chain propagating along the a-axis direction. An analysis of the calculated Hirshfeld surfaces and two-dimensional fingerprint plots point to the significance of H⋯H (58.4%), S⋯H/H⋯S (17.1%), C⋯H/H⋯C (8.2%) and O⋯H/H⋯O (4.9%) contacts in the packing. The energies of the most significant inter­actions, i.e. the N—H⋯S and C—H⋯π inter­actions have their most significant contributions from electrostatic and dispersive components, respectively. The energies of two other identified close contacts at close to van der Waals distances, i.e. a thione–sulfur and meth­oxy­benzene–hydrogen contact (occurring within the chains along the a axis) and between methyl­ene-H atoms (occurring between chains to consolidate the three-dimensional architecture), are largely dispersive in nature.

A copper(II) dimer with the deprotonated anion of 2-bromo­nicotinic acid (2-BrnicH), namely, tetrakis(μ-2-bromonicotinato-κ2O:O')bis[aquacopper(­II)](Cu—Cu), [Cu2(H2O)2(C6H3BrNO2)4] or [Cu2(H2O)2(2-Brnic)4], (1), was prepared by the reaction of copper(II) chloride dihydrate and 2-bromo­nicotinic acid in water. The copper(II) ion in 1 has a distorted square-pyramidal coordination environment, achieved by four carboxyl­ate O atoms in the basal plane and the water mol­ecule in the apical position. The pair of symmetry-related copper(II) ions are connected into a centrosymmetric paddle-wheel dinuclear cluster [Cu⋯Cu = 2.6470 (11) Å] via four O,O'-bridging 2-bromo­nicotinate ligands in the syn-syn coordination mode. In the extended structure of 1, the cluster mol­ecules are assembled into an infinite two-dimensional hydrogen-bonded network lying parallel to the (001) plane via strong O—H⋯O and O—H⋯N hydrogen bonds, leading to the formation of various hydrogen-bond ring motifs: dimeric R22(8) and R22(16) loops and a tetra­meric R44(16) loop. The Hirshfeld surface analysis was also performed in order to better illustrate the nature and abundance of the inter­molecular contacts in the structure of 1.

The title compound, C15H17NO2S, was synthesized via a substitution reaction between 4-methyl­benzyl­amine and p-toluene­sulfonyl chloride. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules, forming ribbons running along the b-axis direction. One of the aromatic rings hosts two inter­molecular C—H⋯π inter­actions that link these hydrogen-bonded ribbons into a three-dimensional network.

The structure of (μ-1κN:2(η2),κ2N,N'-(2-{[2,6-bis(propan-2-yl)phen­yl]aza­nid­yl}eth­yl)[2-(1H-inden-1-yl)eth­yl]aza­nido)(1,4,7,10,13,16-hexa­oxa­cyclo­octa­dec­ane-1κ6O)lithiumtin, [LiSn(C8H16O4)(C25H31N2)], at 100 K has monoclinic (P21/n) symmetry. Analysis of the coordination of the Sn to the indenyl ring shows that the Sn inter­acts in an η2 fashion. A database survey showed that whilst this coordination mode is unusual for Ge and Pb compounds, Sn displays a wider range of coordination modes to cyclo­penta­dienyl ligands and their derivatives.

The asymmetric unit of the title 1:2 co-crystal, C14H14N4O2·2C7H5ClO2, comprises two half mol­ecules of oxalamide (4LH2), as each is disposed about a centre of inversion, and two mol­ecules of 4-chloro­benzoic acid (CBA), each in general positions. Each 4LH2 mol­ecule has a (+)anti­periplanar conformation with the pyridin-4-yl residues lying to either side of the central, planar C2N2O2 chromophore with the dihedral angles between the respective central core and the pyridyl rings being 68.65 (3) and 86.25 (3)°, respectively, representing the major difference between the independent 4LH2 mol­ecules. The anti conformation of the carbonyl groups enables the formation of intra­molecular amide-N—H⋯O(amide) hydrogen bonds, each completing an S(5) loop. The two independent CBA mol­ecules are similar and exhibit C6/CO2 dihedral angles of 8.06 (10) and 17.24 (8)°, indicating twisted conformations. In the crystal, two independent, three-mol­ecule aggregates are formed via carb­oxy­lic acid-O—H⋯N(pyrid­yl) hydrogen bonding. These are connected into a supra­molecular tape propagating parallel to [100] through amide-N—H⋯O(amide) hydrogen bonding between the independent aggregates and ten-membered {⋯HNC2O}2 synthons. The tapes assemble into a three-dimensional architecture through pyridyl- and methyl­ene-C—H⋯O(carbon­yl) and CBA-C—H⋯O(amide) inter­actions. As revealed by a more detailed analysis of the mol­ecular packing by calculating the Hirshfeld surfaces and computational chemistry, are the presence of attractive and dispersive Cl⋯C=O inter­actions which provide inter­action energies approximately one-quarter of those provided by the amide-N—H⋯O(amide) hydrogen bonding sustaining the supra­molecular tape.

A peptide biphenyl hybrid compound {systematic name: dimethyl 2,2'-[((2S,2'S)-2,2'-{[(2S,2'S)-1,1'-([1,1'-biphen­yl]-2,2'-dicarbon­yl)bis­(pyrrolidine-1,2-diyl-2-carbon­yl)]bis­(aza­nedi­yl)}bis­(3-phenyl­propano­yl))bis­(aza­nedi­yl)](2S,2'S)-dipropionate hemihydrate}, C50H56N6O10·0.5H2O, was prepared by coupling of [1,1'-biphen­yl]-2,2'-dicarbonyl dichloride, tri­ethyl­amine and the tripeptide Pro–Phe–Ala in CH2Cl2 at 273 K under an N2 atmosphere. In the crystal, the asymmetric unit contains the peptide biphenyl hybrid accompanied by one-half of a water mol­ecule. A C atom of one of the proline rings is disordered between two positions in a 0.746 (11):0.254 (11) ratio. An important structural aspect of peptide compounds is their capacity to self-associate mediated by inter­molecular and intra­molecular hydrogen bonding. This characteristic can be useful in understanding the inter­actions between peptides and biomacromolecular targets, as well as to explain peptide properties.

The unit cell of the title compound, [Zn(C17H18N3O4)2]·CH4O·C2H6O, contains two complex mol­ecules related by an inversion centre, plus one methanol and one ethanol solvent molecule per complex molecule. In each complex, two deprotonated pyridine aroylhydrazone ligands {3,4,5-trimeth­oxy-N'-[1-(pyridin-2-yl)ethyl­idene]benzohydrazide} coordinate to the ZnII ion through the N atoms of the pyridine group and the ketamine, and, additionally, through the O atom of the enolate group. In the crystal, dimers are formed by π–π inter­actions between the planar ligand moieties, which are further connected by C⋯O and C⋯C inter­actions. The inter­molecular inter­actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H⋯H (44.8%), H⋯C/C⋯H (22.2%), H⋯O/O⋯H (18.7%) and C⋯C (3.9%) inter­actions.

The crystal structure of the title compound, [Ni(C13H11N2O2)(H2O)4]Br3·2H2O, contains an octa­hedral NiII atom coordinated to the enol form of 1,3-di­pyridyl­propane-1,3-dione (dppo) and four water mol­ecules. Both pyridyl rings on the ligand are protonated, forming pyridinium rings and creating an overall ligand charge of +1. The protonated nitro­gen-containing rings are involved in hydrogen-bonding inter­actions with neighoring bromide anions. There are many additional hydrogen-bonding inter­actions involving coordinated water mol­ecules on the NiII atom, bromide anions and hydration water mol­ecules.

Two new mononuclear metal complexes involving the bidentate Schiff base ligand 2,4,6-trimethyl-N-[(pyridin-2-yl)methyl­idene]aniline (C15H16N2 or PM-TMA), [Mn(NCS)2(PM-TMA)2] (I) and [Ni(NCS)2(PM-TMA)2] (II), were synthesized and their structures determined by single-crystal X-ray diffraction. Although the title compounds crystallize in different crystal systems [triclinic for (I) and monoclinic for (II)], both asymmetric units consist of one-half of the complex mol­ecule, i.e. one metal(II) cation, one PM-TMA ligand, and one N-bound thio­cyanate anion. In both complexes, the metal(II) cation is located on a centre of inversion and adopts a distorted octa­hedral coordination environment defined by four N atoms from two symmetry-related PM-TMA ligands in the equatorial plane and two N atoms from two symmetry-related NCS− anions in a trans axial arrangement. The tri­methyl­benzene and pyridine rings of the PM-TMA ligand are oriented at dihedral angles of 74.18 (7) and 77.70 (12)° for (I) and (II), respectively. The subtle change in size of the central metal cations leads to a different crystal packing arrangement for (I) and (II) that is dominated by weak C—H⋯S, C—H⋯π, and π–π inter­actions. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to qu­antify these inter­molecular contacts, and indicate that the most significant contacts in packing are H⋯H [48.1% for (I) and 54.9% for (II)], followed by H⋯C/C⋯H [24.1% for (I) and 15.7% for (II)], and H⋯S/S⋯H [21.1% for (I) and 21.1% for (II)].

The title compound, {[Ba7(C3H5O2)14]·0.946C3H6O2·4H2O}n, is represented by a metal–organic framework structure that is held together by Ba—O—Ba bonds, as well as by O—H⋯O hydrogen bonds of moderate strength. The structure comprises of four independent Ba2+ cations (one of which is situated on a twofold rotation axis), seven independent propionate and two independent water mol­ecules. The bond-valence sums of all the cations indicate a slight overbonding. There is also an occupationally, as well as a positionally disordered propionic acid mol­ecule present in the structure. Its occupation is slightly lower than the full occupation while the disordered mol­ecules occupy two positions related by a rotation about a twofold rotation axis. In addition, the methyl group in the symmetry-independent propionic acid mol­ecule is also disordered, and occupies two positions. Each propionic acid mol­ecule coordinates to just one cation from a pair of symmetry-equivalent Ba2+ sites and is simultaneously bonded by an O—H⋯Opropionate hydrogen bond. This means that on a microscopic scale, the coordination number of the corresponding Ba2+ site is either 9 or 10. The methyl as well as hy­droxy hydrogen atoms of the disordered propionic acid mol­ecule were not determined.

The title compound, C24H27Cl2NOS, contains 1,4-benzo­thia­zine and 2,4-di­chloro­phenyl­methyl­idene units in which the di­hydro­thia­zine ring adopts a screw-boat conformation. In the crystal, inter­molecular C—HBnz⋯OThz (Bnz = benzene and Thz = thia­zine) hydrogen bonds form chains of mol­ecules extending along the a-axis direction, which are connected to their inversion-related counterparts by C—HBnz⋯ClDchlphy (Dchlphy = 2,4-di­chloro­phen­yl) hydrogen bonds and C—HDchlphy⋯π (ring) inter­actions. These double chains are further linked by C—HDchlphy⋯OThz hydrogen bonds, forming stepped layers approximately parallel to (012). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.7%), C⋯H/H⋯C (23.7%), Cl⋯H/H⋯Cl (18.9%), O⋯H/H⋯O (5.0%) and S⋯H/H⋯S (4.8%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, C—HDchlphy⋯OThz, C—HBnz⋯OThz and C—HBnz⋯ClDchlphy hydrogen-bond energies are 134.3, 71.2 and 34.4 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. The two carbon atoms at the end of the nonyl chain are disordered in a 0.562 (4)/0.438 (4) ratio.

In the crystal structure of the title compound, [Fe(NCS)2(C12H9NO)2(CH4O)2], the FeII cations are octa­hedrally coordinated by two N atoms of 4-benzoyl­pyridine ligands, two N atoms of two terminal iso­thio­cyanate anions and two methanol mol­ecules into discrete complexes that are located on centres of inversion. These complexes are linked via inter­molecular O—H⋯O hydrogen bonds between the methanol O—H H atoms and the carbonyl O atoms of the 4-benzoyl­pyridine ligands, forming layers parallel to (101). Powder X-ray diffraction proved that a pure sample was obtained but that this compound is unstable and transforms into an unknown crystalline phase within several weeks. However, the solvent mol­ecules can be removed by heating in a thermobalance, which for the aged sample as well as the title compound leads to the formation of a compound with the composition Fe(NCS)2(4-benzoyl­pyridine)2, which exhibits a powder pattern that is similar to that of Mn(NCS)2(4-benzoyl­pyridine)2.

The pyran­opyran amide (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetra­hydro­pyrano[3,2-b]pyran-2-carboxamide, C9H9NO4, 3, was prepared by a chemoselective hydration of the corresponding nitrile, 2, using a heterogeneous catalytic method based on copper(II) supported on mol­ecular sieves, in the presence of acetaldoxime. Compound 3 belongs to a new class of pyran­opyrans that possess anti­bacterial and phytotoxic activity. Crystallographic analysis of 3 shows a bent structure for the cis-fused bicyclic pyran­opyran, similar to nitrile 2. Evidence of an intra­molecular hydrogen bond involving the amide group and ring oxygen was not observed; however, two separate inter­molecular hydrogen-bonding inter­actions were observed between the amide hydrogen atoms and adjacent carbonyl oxygen atoms along the b- and a-axis directions. The latter inter­action may also be supported by an inter­molecular C—H⋯O hydrogen bond. The lattice is filled out by close-packed layers of this hydrogen-bonded network along the c-axis direction, related from one to the next by a 21 screw axis.

The crystal structure of title salt, C14H36N44+·2ClO4−·2Cl−, has been determined using synchrotron radiation at 220 K. The structure determination reveals that protonation has occurred at all four amine N atoms. The asymmetric unit contains one half-cation (completed by crystallographic inversion symmetry), one perchlorate anion and one chloride anion. A distortion of the perchlorate anion is due to its involvement in hydrogen-bonding inter­actions with the cations. The crystal structure is consolidated by inter­molecular hydrogen bonds involving the 1,4,8,11-tetra­methyl-1,4,8,11-tetra­azonia­cyclo­tetra­decane N—H and C—H groups as donor groups, and the O atoms of the perchlorate and chloride anion as acceptor groups, giving rise to a three-dimensional network.

A new organic–inorganic hybrid salt [L]2[MnCl4] (I) where L+ is the 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium cation, is built of discrete organic cations and tetra­chlorido­manganate(II) anions. The L+ cation was formed in situ in the oxidative cyclo­condensation of 2-pyridine­carbaldehyde and CH3NH2·HCl in methanol. The structure was refined as a two-component twin using PLATON (Spek, 2020) to de-twin the data. The twin law (−1 0 0 0 − 1 0 0.5 0 1) was applied in the refinement where the twin component fraction refined to 0.155 (1). The compound crystallizes in the space group P21/c with two crystallographically non-equivalent cations in the asymmetric unit, which possess similar structural conformations. The fused pyridinium and imidazolium rings of the cations are virtually coplanar [dihedral angles are 0.89 (18) and 0.78 (17)°]; the pendant pyridyl rings are twisted by 36.83 (14) and 36.14 (13)° with respect to the planes of the remaining atoms of the cations. The tetra­hedral MnCl42– anion is slightly distorted with the Mn—Cl distances falling in the range 2.3469 (10)–2.3941 (9) Å. The distortion value of 0.044 relative to the ideal tetra­hedron was obtained by continuous shape measurement (CShM) analysis. In the crystal, the cations and anions form separate stacks propagating along the a-axis direction. The organic cations display weak π–π stacking. The anions, which are stacked identically one above the other, demonstrate loose packing; the minimum Mn⋯Mn separation in the cation stack is approximately 7.49 Å. The investigation of the fluorescent properties of a powdered sample of (I) showed no emission. X-band EPR data for (I) at 293 and 77 K revealed broad fine structure signals, indicating moderate zero-field splitting.

The title compound, C20H36O2·CH3OH [systematic name: (3S)-4-[(S)-3-hy­droxy-3-methyl­pent-4-en-1-yl]-3,4a,8,8-tetra­methyl­deca­hydro­naphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z' = 2. The sclareol mol­ecule comprises two trans-fused cyclo­hexane rings, each having an equatorially oriented hydroxyl group, and a 3-methyl­pent-1-en-3-ol side chain. In the crystal, Os—H⋯Os, Os—H⋯Om, Om—H⋯Os and Om—H⋯Om (s = sclareol, m = methanol) hydrogen bonds connect neighboring mol­ecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC50 = 66.4 ± 1.0 µM ml−1) against standard miltefosine (IC50 = 25.8 ± 0.2 µM ml−1).

In the title mol­ecule, C12H13N3O2S, the benzo­thia­zine moiety is slightly non-planar, with the imidazolidine portion twisted only a few degrees out of the mean plane of the former. In the crystal, a layer structure parallel to the bc plane is formed by a combination of O—HHydethy⋯NThz hydrogen bonds and weak C—HImdz⋯OImdz and C—HBnz⋯OImdz (Hydethy = hy­droxy­ethyl, Thz = thia­zole, Imdz = imidazolidine and Bnz = benzene) inter­actions, together with C—HImdz⋯π(ring) and head-to-tail slipped π-stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) Å] inter­actions between thia­zole rings. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (47.0%), H⋯O/O⋯H (16.9%), H⋯C/C⋯H (8.0%) and H⋯S/S⋯H (7.6%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, C—H⋯N and C—H⋯O hydrogen-bond energies are 68.5 (for O—HHydethy⋯NThz), 60.1 (for C—HBnz⋯OImdz) and 41.8 kJ mol−1 (for C—HImdz⋯OImdz). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state.

Chalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di­hydro­pyrazole-1-carbo­thio­amides using a cyclo­condensation reaction with thio­semicarbazide. The chalcones 1-(4-chloro­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol­ecules are linked into sheets by two independent C—H⋯π(arene) inter­actions, both involving the same aryl ring with one C—H donor approaching each face. In each of the products (RS)-3-(4-chloro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth­oxy­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn­yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol­ecules are linked into chains of edge-fused rings by a combination of N—H⋯S and C—H⋯S hydrogen bonds. The mol­ecules of (VI) are linked into sheets by a combination of N—H⋯S, N—H⋯N and C—H⋯π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.

The crystal structures of tris­[9,9-dihexyl-2-(5-meth­oxy­pyridin-2-yl-κN)-9H-fluoren-3-yl-κC3]iridium pentane monosolvate, [Ir(C31H38NO)3]·C5H12, (I), di-μ2-chlorido-bis­{bis­[2-(5-fluoro­pyridin-2-yl)-9,9-dihexyl-9H-fluoren-3-yl]iridium} pentane 0.3-solvate, [Ir2(C30H35FN)4Cl2]·0.3C5H12, (II), di-μ2-cyanato-bis­{bis­[9,9-dihexyl-2-(5-meth­oxy­pyridin-2-yl)-9H-fluoren-1-yl]iridium} pentane monosolvate, [Ir2(C31H38NO)4(NCO)2(NCO)2]·C5H12, (III), and {μ-N,N'-bis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]oxamidato}bis(bis{2-[4-(2,4,6-trimethylphenyl)pyridin-2-yl]phenyl-κ2C1,N'}iridium)–chloro­benzene–pentane (1/2.3/0.4), [Ir2(C20H19N)4(C18H6F12N2O2)]·2.3C6H5Cl·0.4C5H12, (IV), synthesized in the quest for organic light-emitting devices, were determined. The bis-μ2-chloro and bis-μ2-cyanato complexes have ΔΔ and ΛΛ configurations of the distorted octa­hedral Ir centres in racemic crystals, whereas the oxamido complex has a centrosymmetric (meso) structure with the ΔΛ configuration. The bridging oxamido moiety has a nearly planar anti geometry. All structures show substantial disorder of both host mol­ecules and solvents of crystallization.

The title pyrazine dicarboxamide ligand, N2,N3-bis­(quinolin-8-yl)pyrazine-2,3-dicarboxamide (H2L1), C24H16N6O2, has a twisted conformation with the outer quinoline groups being inclined to the central pyrazine ring by 9.00 (6) and 78.67 (5)°, and by 79.94 (4)° to each other. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming layers parallel to the (10overline{1}) plane, which are in turn linked by offset π–π inter­actions [inter­centroid distances 3.4779 (9) and 3.6526 (8) Å], forming a supra­molecular three-dimensional structure. Reaction of the ligand H2L1 with Cu(ClO4)2 in aceto­nitrile leads to the formation of the binuclear complex, [μ-(3-{hy­droxy[(quinolin-8-yl)imino]­meth­yl}pyrazin-2-yl)[(quinolin-8-yl)imino]­methano­lato]bis­[diaceto­nitrile­copper(II)] tris­(per­chlor­ate) aceto­nitrile disolvate, [Cu2(C24H15N6O2)(CH3CN)4](ClO4)3·2CH3CN or [Cu2(HL1−)(CH3CN)4](ClO4)3·2CH3CN (I). In the cation of complex I, the ligand coordinates to the copper(II) atoms in a bis-tridentate fashion. A resonance-assisted O—H⋯O hydrogen bond is present in the ligand; the position of this H atom was located in a difference-Fourier map. Both copper(II) atoms are fivefold coordinate, being ligated by three N atoms of the ligand and by the N atoms of two aceto­nitrile mol­ecules. The first copper atom has a perfect square-pyramidal geometry while the second copper atom has a distorted shape. In the crystal, the cation and perchlorate anions are linked by a number of C—H⋯O hydrogen bonds, forming a supra­molecular three-dimensional structure.

The title compound, C13H16ClNO, contains a methyl­piperidine ring in the stable chair conformation. The mean plane of the twisted piperidine ring subtends a dihedral angle of 39.89 (7)° with that of the benzene ring. In the crystal, weak C—H⋯O inter­actions link the mol­ecules along the a-axis direction to form infinite mol­ecular chains. H⋯H inter­atomic inter­actions, C—H⋯O inter­molecular inter­actions and weak dispersive forces stabilize mol­ecular packing and form a supra­molecular network, as established by Hirshfeld surface analysis.

In the title compound, [Cu(C16H8Br3N2O)2]·C2H6OS, the CuII atom is tetra­coordinated in a square-planar coordination, being surrounded by two N atoms and two O atoms from two N,O-bidentate (E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-olate ligands. The two N atoms and two O atoms around the metal center are trans to each other, with an O—Cu—O bond angle of 177.90 (16)° and a N—Cu—N bond angle of 177.8 (2)°. The average distances between the CuII atom and the coordinated O and N atoms are 1.892 (4) and 1.976 (4) Å, respectively. In the crystal, complexes are linked by C—H⋯O hydrogen bonds and by π–π inter­actions involving adjacent naphthalene ring systems [centroid–centroid distance = 3.679 (4) Å]. The disordered DMSO mol­ecules inter­act weakly with the complex mol­ecules, being positioned in the voids left by the packing arrangement of the square-planar complexes. The DMSO solvent mol­ecule is disordered over two positions with occupancies of 0.70 and 0.30.

The central thia­zolidine ring of the title salt, C16H16N3S+·Br−, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N—H⋯Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (46.4%), C⋯H/H⋯C (18.6%) and H⋯Br/Br⋯H (17.5%) inter­actions.

In the title compound, C22H27NO, the piperidine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperidine ring and the phenyl rings are 89.78 (7) and 48.30 (8)°. In the crystal, mol­ecules are linked into chains along the b-axis direction by C—H⋯O hydrogen bonds. The DFT/B3LYP/6–311 G(d,p) method was used to determine the HOMO–LUMO energy levels. The mol­ecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the inter­molecular inter­actions in the mol­ecule.

The mol­ecular structure of the title compound, C11H15NO2S, features a sulfonamide group with S=O bond lengths of 1.4357 (16) and 1.4349 (16) Å, an S—N bond length of 1.625 (2) Å, and an S—C bond length of 1.770 (2) Å. When viewing the mol­ecule down the S—N bond, both N—C bonds of the pyrrolidine ring are oriented gauche to the S—C bond with torsion angles of −65.6 (2)° and 76.2 (2)°. The crystal structure features both intra- and inter­molecular C—H⋯O hydrogen bonds, as well as inter­molecular C—H⋯π and π–π inter­actions, leading to the formation of sheets parallel to the ac plane.

In the crystal of the title Schiff base compound, C13H9ClN2O2, [CNBA; systematic name: (E)-N-(4-chloro­phen­yl)-1-(4-nitro­phen­yl)methanimine], the CNBA mol­ecule shows whole-mol­ecule disorder (occupancy ratio 0.65:0.35), with the disorder components related by a twofold rotation about the shorter axis of the mol­ecule. The aromatic rings are inclined to each other by 39.3 (5)° in the major component and by 35.7 (9)° in the minor component. In the crystal, C—H⋯O hydrogen bonds predominate in linking the major components, while weak C—H⋯Cl inter­actions predominate in linking the minor components. The result is the formation of corrugated layers lying parallel to the ac plane. The crystal packing was analysed using Hirshfeld surface analysis and compared with related structures.

Two polymorphs of the title compound, C19H16N2O3, were obtained from ethano­lic (polymorph I) and methano­lic solutions (polymorph II), respectively. Both polymorphs crystallize in the monoclinic system with four formula units per cell and a complete mol­ecule in the asymmetric unit. The main difference between the mol­ecules of (I) and (II) is the reversed position of the hy­droxy group of the carb­oxy­lic function. All other conformational features are found to be similar in the two mol­ecules. The different orientation of the OH group results in different hydrogen-bonding schemes in the crystal structures of (I) and (II). Whereas in (I) inter­molecular O—H⋯O hydrogen bonds with the pyridazinone carbonyl O atom as acceptor generate chains with a C(7) motif extending parallel to the b-axis direction, in the crystal of (II) pairs of inversion-related O—H⋯O hydrogen bonds with an R22(8) ring motif between two carb­oxy­lic functions are found. The inter­molecular inter­actions in both crystal structures were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

In the title compound, C18H18ClN3O2S, the dihedral angle between the fused pyrazole and pyridine rings is 3.81 (9)°. The benzene ring forms dihedral angles of 35.08 (10) and 36.26 (9)° with the pyrazole and pyridine rings, respectively. In the crystal, weak C—H⋯O hydrogen bonds connect mol­ecules along [100].

The title compound, [Mn(S4)(C8H20N4)], was accidentally obtained by the hydro­thermal reaction of Mn(ClO4)2·6H2O, cyclen (cyclen = 1,4,7,10-tetra­aza­cyclo­dodeca­ne) and Na3SbS4·9H2O in water at 413 K, indicating that polysulfide anions might represent inter­mediates in the synthesis of thio­metallate compounds using Na3SbS4·9H2O as a reactant. X-ray powder diffraction proves that the sample is slightly contaminated with NaSb(OH)6 and an unknown crystalline phase. The crystal investigated was twinned with a twofold rotation axis as the twin element, and therefore a twin refinement using data in HKLF-5 format was performed. The asymmetric unit of the title compound consists of one MnII cation, one [S4]2− anion and one cyclen ligand in general positions. The MnII cation is sixfold coordinated by two cis-S atoms of the [S4]2− anions, as well as four N atoms of the cyclen ligand within an irregular coordination. The complexes are linked via pairs of N—H⋯S hydrogen bonds into chains, which are further linked into layers by additional N—H⋯S hydrogen bonding. These layers are connected into a three-dimensional network by inter­molecular N—H⋯S and C—H⋯S hydrogen bonding. It is noted that only one similar complex with MnII is reported in the literature.

In the title compound, C10H8N8·2H2O or H2bmtz·2H2O [bmtz = 3,6-bis­(2'-pyrimid­yl)-1,2,4,5-tetra­zine], the asymmetric unit consists of one-half mol­ecule of H2bmtz and one water mol­ecule, the whole H2bmtz mol­ecule being generated by a crystallographic twofold rotation axis passing through the middle point of the 1,4-di­hydro-1,2,4,5-tetra­zine moiety. In the crystal, N—H⋯O, N—H⋯N, O—H⋯O hydrogen bonds and aromatic π–π stacking inter­actions link the components into a three-dimensional supra­molecular network. Hirshfeld surface analysis was used to further investigate the inter­molecular inter­actions in the crystal structure.

In the title hydrated complex, [Co(C15H10ClN3)2]Cl2·4H2O, the complete dication is generated by overline{4} symmetry. The CoN6 moiety shows distortion from regular octa­hedral geometry with the trans bond angles of two N—Co—N units being 160.62 (9)°. In the crystal, O—H⋯Cl and C—H⋯O inter­actions link the components into (001) sheets. The title compound exhibits blue-light emission, as indicated by photoluminescence data, and a HOMO–LUMO energy separation of 2.23 eV was obtained from its diffuse reflectance spectrum.

In the title compound, C9H10ClNOS, the amide functional group –C(=O)NH– adopts a trans conformation with the four atoms nearly coplanar. This conformation promotes the formation of a C(4) hydrogen-bonded chain propagating along the [010] direction. The central part of the mol­ecule, including the six-membered ring, the S and N atoms, is fairly planar (r.m.s. deviation of 0.014). The terminal methyl group and the C(=O)CH2 group are slightly deviating out-of-plane while the terminal Cl atom is almost in-plane. Hirshfeld surface analysis of the title compound suggests that the most significant contacts in the crystal are H⋯H, H⋯Cl/Cl⋯H, H⋯C/C⋯H, H⋯O/O⋯H and H⋯S/S⋯H. π–π inter­actions between inversion-related mol­ecules also contribute to the crystal packing. DFT calculations have been performed to optimize the structure of the title compound using the CAM-B3LYP functional and the 6–311 G(d,p) basis set. The theoretical absorption spectrum of the title compound was calculated using the TD–DFT method. The analysis of frontier orbitals revealed that the π–π* electronic transition was the major contributor to the absorption peak in the electronic spectrum.

A one-dimensional nickel(II) coordination polymer with the mixed ligands 6-fluoro­nicotinate (6-Fnic) and 4,4'-bi­pyridine (4,4'-bpy), namely, catena-poly[[di­aqua­bis­(6-fluoro­pyridine-3-carboxyl­ato-κO)nickel(II)]-μ-4,4'-bi­pyri­dine-κ2N:N'] trihydrate], {[Ni(6-Fnic)2(4,4'-bpy)(H2O)2]·3H2O}n, (1), was prepared by the reaction of nickel(II) sulfate hepta­hydrate, 6-fluoro­nicotinic acid (C6H4FNO2) and 4,4'-bi­pyridine (C10H8N2) in a mixture of water and ethanol. The nickel(II) ion in 1 is octa­hedrally coordinated by the O atoms of two water mol­ecules, two O atoms from O-monodentate 6-fluoro­nicotinate ligands and two N atoms from bridging 4,4'-bi­pyridine ligands, forming a trans isomer. The bridging 4,4'-bi­pyridine ligands connect symmetry-related nickel(II) ions into infinite one-dimensional polymeric chains running in the [1overline{1}0] direction. In the extended structure of 1, the polymeric chains and lattice water mol­ecules are connected into a three-dimensional hydrogen-bonded network via strong O—H⋯O and O—H⋯N hydrogen bonds, leading to the formation of distinct hydrogen-bond ring motifs: octa­meric R88(24) and hexa­meric R86(16) loops.

The title compound, C11H9N3OS, (I), crystallizes in the monoclinic space group P21/n. The mol­ecular conformation is nearly planar and features an intra­molecular chalcogen bond between the thio­phene S and the imine N atoms. Within the crystal, the strongest inter­actions between mol­ecules are the N—H⋯O hydrogen bonds, which organize them into inversion dimers. The dimers are linked through short C—H⋯N contacts and are stacked into layers propagating in the (001) plane. The crystal structure features π–π stacking between the pyridine aromatic ring and the azomethine double bond. The calculated energies of pairwise inter­molecular inter­actions within the stacks are considerably larger than those found for the inter­actions between the layers.

The crystal structure of title compound, (C14H36N4)[CrO3Cl]2Cl2, has been determined by synchrotron radiation X-ray crystallography at 220 K. The macrocyclic cation lies across a crystallographic inversion center and hence the asymmetric unit contains one half of the organic cation, one chloro­chromate anion and one chloride anion. Both the Cl− anion and chloro­chromate Cl atom are involved in hydrogen bonding. In the crystal, hydrogen bonds involving the 1,4,8,11-tetra­methyl-1,4,8,11-tetra­azonia­cyclo­tetra­decane (TMC) N—H groups and C—H groups as donor groups and three O atoms of the chloro­chromate and the chloride anion as acceptor groups link the components, giving rise to a three-dimensional network.

The title compound, a major animal feed supplement, abbreviated as HMTBA and alternatively called dl-me­thio­nine hy­droxy analogue, C5H10O3S, (I), was isolated in pure anhydrous monomeric form. The melting point is 302.5 K and the compound crystallizes in the monoclinic space group P21/c, with two conformationally non-equivalent mol­ecules [(IA) and (IB)] in the asymmetric unit. The crystal structure is formed by alternating polar and non-polar layers running along the bc plane and features an extensive hydrogen-bonding network within the polar layers. The Hirshfeld surface analysis revealed a significant contribution of non-polar H⋯H and H⋯S inter­actions to the packing forces for both mol­ecules.

Two salts were prepared by methyl­ation of the respective imidazoline-2-thione at the sulfur atom, using Meerwein's salt (tri­methyl­oxonium tetra­fluorido­borate) in CH2Cl2. 1,3-Dimeth­oxy-2-(methyl­sulfan­yl)imidazolium tetra­fluorido­borate (1), C6H11N2O2S+·BF4−, displays a syn conformation of its two meth­oxy groups relative to each other whereas the two benz­yloxy groups present in 1,3-dibenz­yloxy-2-(methyl­sulfan­yl)imidazolium tetra­fluorido­borate (2), C18H19N2O2S+·BF4−, adopt an anti conformation. In the mol­ecules of 1 and 2, the methyl­sulfanyl group is rotated out of the plane of the respective heterocyclic ring. In both crystal structures, inter­molecular inter­actions are dominated by C—H⋯F—B contacts, leading to three-dimensional networks. The tetra­fluorido­borate counter-ion of 2 is disordered over three orientations (occupancy ratio 0.42:0.34:0.24), which are related by rotation about one of the B—F bonds.

The asymmetric unit of the title compound, C5H7N2O+·C4H4NO4S−, contains one cation and one anion. The 6-methyl-2,2,4-trioxo-2H,4H-1,2,3-oxa­thia­zin-3-ide anion adopts an envelope conformation with the S atom as the flap. In the crystal, the anions and cations are held together by N—H⋯O, N—H⋯N, O—H⋯O and C—H⋯O hydrogen bonds, thus forming a three-dimensional structure. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal packing is dominated by O⋯H/H⋯O (43.1%) and H⋯H (24.2%) contacts.

4-[(Morpholin-4-yl)carbothioyl]benzoic acid, C12H13NO3S, a novel phen­yl(morpholino)methane­thione derivative, crystallizes in the monoclinic space group P21/n. The morpholine ring adopts a chair conformation and the carb­oxy­lic acid group is bent out slightly from the benzene ring mean plane. The mol­ecular geometry of the carb­oxy­lic group is characterized by similar C—O bond lengths [1.266 (2) and 1.268 (2) Å] as the carboxyl­ate H atom is disordered over two positions. This mol­ecular arrangement leads to the formation of dimers through strong and centrosymmetric low barrier O—H⋯O hydrogen bonds between the carb­oxy­lic groups. In addition to these inter­molecular inter­actions, the crystal packing consists of two different mol­ecular sheets with an angle between their mean planes of 64.4 (2)°. The cohesion between the different layers is ensured by C—H⋯S and C—H⋯O inter­actions.