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A new complex of Zn(II), with 5-chloro-2-methylbenzoxazole ligand (L), has been synthesized by the reaction of zinc dichloride with the ligand (L= C8H6ClNO) in ethanol solution: dichloridobis(5-chloro-2-methyl-1,3-benzoxazole)-zinc(II), C16H12Cl4N2O2Zn. The synthesized complex has been fully characterized by elemental analysis, molar conductivity, FT‑IR, UV‑Vis, and single-crystal X-ray diffraction (XRD). The XRD analysis reveals that the complex has a 1:2 metal-to-ligand ratio. The zinc(II) complex has a distorted tetrahedral geometry with two coordinated nitrogen atoms from the ligand. Density Functional Theory (DFT) calculations were performed at the B3LYP level of theory using the LANL2DZ basis set for metal complex and the 6-31G(d) basis set for non-metal elements to determine the optimum geometry structure of the complex, and the calculated HOMO and LUMO orbital energies were presented. A natural bond orbital (NBO) analysis was carried out on the molecules to analyze the atomic charge distribution before and after the complexation of the ligand. The Hirshfeld surface mapped over dnorm, shape index, and curvature exhibited strong H...Cl/Cl...H and H...H intermolecular interactions as the principal contributors to crystal packing.

Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3-[2-({[(3-bromophenyl)formamido]methanethioyl}amino)phenyl]thiourea (10) and 3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea (12) gave a percentage viability of 17.9±5.6% and 11.2±0.9% against Trypanosoma brucei. Single crystal X-ray diffraction analysis of 1-benzoyl-3-(5-methyl-2-{[(phenylformamido)methanethioyl]amino}phenyl)thiourea (1), 3-benzoyl-1-(2-{[(phenylformamido)methanethioyl]amino}ethyl)thiourea (11), 3-benzoyl-1-{[(phenylformamido)methanethioyl]amino}thiourea (12) and 3-benzoyl-1-(4-{[(phenylformamido)methanethioyl]amino}butyl)thiourea (14) have been presented. 1-(3-Bromobenzoyl)-3-[2-({[(3-bromophenyl)formamido]methanethioyl}amino)phenyl]thiourea (10) gave a percentage inhibition of 97.03±0.37% against HIV-1 protease enzyme at a concentration of 100 µM.

The conformation of the title compound, C34H26F2O6, is cone-shaped, partially determined by intramolecular C—H...O short contacts. The benzene rings at the top of the cone are inclined to one another by 73.10 (7)°, while the benzene rings at the bottom of the cone are inclined to one another by 35.49 (8)°. In the crystal, molecules are linked by C—H...O and C—H...F hydrogen bonds, forming a three-dimensional supramolecular structure. There are also C—H...π contacts present within the framework structure.

A reaction of an acid chloride with a diamine yielded a diamide. m-Toluic acid was chlorinated to m-toluoyl chloride and subsequently reacted with 4-methyl-o-phenylenediamine in pyridine to obtain 3-methyl-N-[2-(3-methylbenzamido)phenylbenzamide (I). 2-(3-Methylphenyl)-1H-benzimidazole (II) has been obtained upon reacting o-phenylenediamine with m-toluic acid in polyphosphoric acid and toluene. The compounds have been characterized by IR, NMR, microanalyses and GC−MS. The crystal structures of the compounds have been discussed. DFT calculations of the frontier orbitals of the precursor compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity in the formation of the diamides and benzimidazoles. The synthesis of the amide from a diamine was seen to be favoured in the presence of a good leaving group attached to the carbonyl as in the case of acid chloride. However, the synthesis of benzimidazoles was found to be favoured in the presence of an excess of a protonating agent and high temperature

In an attempt to synthesize a 2-substituted benzimidazole from the reaction of o-phenylenediamine and isophthalic acid in the presence of acetone and ethanol under microwave irradiation, a salt of the isophthalate ion and 2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepin-5-ium ion was obtained. The condensation of two moles of acetone with the amine groups resulted in the formation of the benzodiazepine which crystallized as an iminium cation forming a salt with the isophthalate anion. The formation of benzodiazepine was also confirmed by performing the reaction of o-phenylenediamine with excess acetone in ethanol under conventional heating conditions. The compounds were characterized by NMR, FTIR, HRMS and microanalysis as well as X-ray crystallography. The reaction mechanism leading to the formation of benzodiazepine is also discussed.

The six-coordinate complex [Re(mps)Cl2(PPh3)] (1) (H3mps = N-(2-amino-3-methylphenyl) salicylideneimine) was prepared by the reaction of [NH4][ReO4] with H3mps in the presence of triphenylphosphine and hydrochloric acid in glacial acetic acid. Crystallization from acetonitrile gave the product 1.CH3CN. The compound was characterized by spectroscopy and X-ray crystallography. The results show that the tridentate mps ligand coordinates via the doubly deprotonated 2-amino nitrogen (which is present in 1 as an imide), the neutral imino nitrogen and the phenolate oxygen. The imide and phenolate oxygen are trans to each other in a distorted octahedral geometry around the rhenium(V) centre, with the two chlorides in cis positions.

In the title compound, C19H13ClO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.16 (3)°. In the crystal, C—H...O contacts connect the molecules into undulating sheets parallel to the bc plane.

In the title compound, C15H12Cl2O3, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C—H...O contact. In the crystal, C—H...O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.

In the title compound, C19H16F3NO6, a quinoline derivative featuring an annealated furan substituent, the mean planes of the carboxy substituents are at an angle of 74.3 (2)°. In the crystal, C—H...O contacts result in undulating chains along [110]. C—H...F contacts also occur. The shortest centroid–centroid distance between rings is 3.3376 (7) Å, involving two furan rings of neighbouring molecules.

In the title compound, C21H23N3O4S·H2O, the methylsulfanyl group is disordered over two sets of sites with site-occupancy factors of 0.631 (11) and 0.369 (11). The dihydropyridine ring adopts an E4 conformation. In the crystal, classical O—H...N, O—H...O and N—H...O hydrogen bonds, as well as C—H...O and C—H...S contacts, connect the molecules into a three-dimensional network.

The asymmetric unit of the title compound, C30H22N2O6, comprises a half-molecule of the cyclobutane derivative. The least-squares planes defined by the respective C atoms of the aromatic substituents intersect at angles of 76.81 (7) and 89.22 (8)° with the least-squares plane defined by the C atoms of the cyclobutane ring. In the crystal, C—H...O contacts connect the molecules into a three-dimensional network. The shortest centroid–centroid distance between the two different aromatic rings is 3.9601 (8) Å.

The title compound, C24H18BrF3N4O4, is a 1,2,3-triazole derivative featuring, among others, a quinoline-derived substituent. In the crystal, C—H...O, C—H...N and C—H...F contacts connect the molecules into a three-dimensional network. The shortest centroid–centroid distance between two aromatic systems is 3.896 (2) Å and is found between the two different six-membered rings of the quinoline scaffold in neighbouring molecules.

In the title compound, C23H27N3O4, the dihydropyridine ring adopts a 1,4B conformation. Intramolecular C—H...O contacts occur. In the crystal, N—H...O and N—H...N hydrogen bonds and C—H...N contacts connect the molecules into strands along the a-axis direction.

In the title pyrimidine derivative, C12H16N2OS, the tetrahydropyrimidine ring adopts an envelope conformation with the C atom of the methylene –CH2– group as the flap. In the crystal, N—H...O and N—H...S hydrogen bonds connect molecules into undulating sheets perpendicular to the a axis.

The asymmetric unit of the title compound, C13H10F3NO3, contains two independent molecules with similar conformations. In the crystal, N—H...O hydrogen bonds link alternating independent molecules into chains in [-110]. In the chain, the quinoline planes of the independent molecules are almost perpendicular to each other, forming a dihedral angle of 89.8 (1)°. π–π interactions between the aromatic rings of quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers, the shortest centroid–centroid distances are 3.495 (1) and 3.603 (1) Å] link the hydrogen-bonded chains into layers parallel to (110). Weak C—H...F and C—H...O interactions further consolidate the crystal packing.

In the title compound, C14H19N3O2, the heterocycle adopts a 1C4 conformation with the N atom being one of the flap atoms. In the crystal, classical N—H...O hydrogen bonds and C—H...O contacts connect the molecules into a three-dimensional network.

In the title compound, C28H19BrF2O2, the C=C double bond is E-configured. In the crystal, C—H...O and C—H...F contacts connect molecules into planes perpendicular to the c axis. The shortest centroid–centroid distance between two aromatic systems is 3.6745 (12) Å between one of the para-fluorophenyl rings and its symmetry-generated equivalent.

In the title compound, C14H10BrClO2, a twofold halogenated derivative of phenylated phenyloxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17)°. In the crystal, C—H...O contacts connect the molecules into chains along the b-axis direction.

In the title molecule, C16H8Cl2FNO, the benzene rings form a dihedral angle of 78.69 (8)°. The F atom is disordered over two positions in a 0.530 (3):0.470 (3) ratio. The crystal packing exhibits π–π interactions between dichloro-substituted rings [centroid–centroid distance = 3.6671 (10) Å] and weak intermolecular C—H...F contacts.

The title compound, C28H19ClF2O2, is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C—H...Cl and C—H...O contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å.

In the title compound, C15H9Cl2FO, the F atom shows positional disorder over two positions, with site-occupancy factors of 0.747 (4) and 0.253 (4). The dihedral angle between the rings is 86.37 (10)°. In the crystal, C—H...O contacts connect the molecules into chains along the c axis. The shortest inter-centroid distance between two aromatic systems is 3.6686 (12) Å and is apparent between the halogenated rings.

The title compound [systematic name: 4-diphenylmethyl-1-(3-phenylprop-2-en-1-yl)-piperazin-1-ium 2-carboxy-4,6-dinitrophenolate], C26H29N2+·C7H3N2O7−, is the dinitrosalicylate salt of a tertiary amine. Deprotonation of the carboxylic acid group occurred on the phenolic hydroxy group. The diazacyclohexane ring adopts a chair conformation. Intramolecular O—H...O and intermolecular C—H...O and N—H...O hydrogen bonds are observed. The N—H...O hydrogen bonds are bifurcated at the H atom and connect the cinnarizinium and 3,5-dinitrosalicylate ions together. Intermolecular C—H...O hydrogen bonds connect the components into layers perpendicular to the crystallographic a axis.

In the title methylbenzoate compound, C16H16O3, the molecule is essentially planar (r.m.s. of all fitted non-H atoms = 0.0370 Å); the dihedral angle between the phenyl rings is 2.30 (7)°. Apart from a C—H...π interaction, no marked intermolecular contacts are obvious.

In the title compound, C16H13FO4, the aromatic rings enclose an angle of 73.68 (6)°. In the crystal, C—H...O and C—H...F contacts connect the molecules into a three-dimensional network. The shortest intercentroid distance between two aromatic π-systems is 3.6679 (7) Å and is apparent between the fluorinated phenyl groups.

The title compound, C15H16F3NO4, is an N-substituted derivative of ortho-trifluoromethylaniline featuring a twofold Michael system. The least-squares planes defined by the atoms of the phenyl ring and the atoms of the Michael system enclose an angle of 15.52 (5)°. Apart from classical intramolecular N—H...O and N—H...F hydrogen bonds, intermolecular C—H...O contacts are observed, the latter connecting the molecules into chains along [110]. The shortest intercentroid distance between two aromatic systems is 3.6875 (9) Å.

In the title compound, C15H8Cl2F2O, the C=C double bond is in the E configuration. In the cyrstal, C—H...O hydrogen bonds connect the molecules into chains along the c axis. A π–π interaction of 3.628 (1) Å is also observed between two polyhalogenated benzene rings. The dichlorosubstituted ring exhibits partial disorder over two sets of sites, with site-occupancy factors of 0.573 (3) and 0.427 (3).

The title compound, C32H18F4N4S2, is a disulfide symmetrically substituted with two diaza-meta-terphenyl groups. In the crystal, the molecule adopts a twisted conformation with a C—S—S—C torsion angle of −91.82 (7)°. One of the 4,6-(4-fluorophenyl)pyrimidine groups is virtually planar, with dihedral angles between the pyrimidine and benzene groups of 4.00 (8) and 5.44 (8)°, wheares the other is non-planar with analogues dihedral angles of 18.69 (8) and 26.60 (8)°. The planar 4,6-(4-fluorophenyl)pyrimidine groups are involved in π–π stacking interactions via their 4-fluorophenyl groups [centroid–centroid distances of 3.8556 (11) and 3.9284 (11) Å] that assemble the molecules into columns extended along the a axis. In addition, the structure is stabilized by C—F...π [F...centroid = 3.4017 (16) Å], C—H...F and C—H...π interactions.

In the title molecular salt, C15H14ClN2OS+·C6H2N3O7−, protonation occurred on the double-bonded N atom. One of the nitro groups shows slight disorder over two orientations, with an occupancy ratio of 0.91:0.09. In the crystal, classical N—H...O hydrogen bonds, as well as C—H...O contacts connect the components into a three-dimensional network. The seven-membered ring adopts a boat-like conformation. The least-squares plane defined by its non-H atoms encloses an angle of 38.99 (6)° with the benzene ring bonded to it.

In the title compound, C20H16N2OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å). The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2)°. In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O—H...N hydrogen bonds. C—H...O contacts and N—H...π(arene) interactions also occur.

The title compound, C28H20F2O2, is a polysubstituted terphenyl derivative bearing a Michael system. The C=C double bond is E configured. In the crystal, C—H...O and C—H...F contacts connect the molecules, forming undulating sheets that lie perpendicular to the crystallographic a axis. The shortest π–π interaction [centroid–centroid distance = 3.7163 (7) Å] involves the para-fluorophenyl ring in the para position to the Michael system, and its symmetry-generated equivalent.

There are two molecules in the asymmetric unit of the title compound, C16H18O, a tertiary alcohol featuring a 2-benzylphenyl substituent. Co-operative O—H...O hydrogen bonds connect the molecules into tetramers.

In the title compound, C28H19F2NO4, a polysubstituted terphenyl derivative bearing a Michael system, the C=C double bond has an E configuration. Two C—H...F contacts connect molecules into inversion dimers. In addition, a C–H...π as well as a C–F...π contact can be identified. The shortest centroid–centroid distance between two aromatic rings is 3.9535 (8) Å, between one of the para-fluorobenzene rings and its symmetry-generated equivalent.

The title compound, C29H22F2O3, is a meta-terphenyl derivative featuring a Michael-system-derived substituent with an E-configured C=C function. In the crystal, C—H...O and C—H...F contacts connect the molecules into planes parallel to (101). The shortest centroid–centroid distance between two aromatic systems is 3.7169 (7) Å and is apparent between the terminal benzene ring of the Michael-system-derived substituent and its symmetry-generated equivalent.

In the title compound, C28H19F3O2, the C=C double bond has an E configuration. In the crystal, C—H...F contacts link the molecules into chains along [111]. The shortest centroid–centroid distance between two π systems is 3.8087 (8) Å and is apparent between the para-fluorophenyl group attached to the Michael system and its symmetry-generated equivalent.

The title compound (systematic name: 4-{3-[2-azatricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl]propyl}-1-(2-hydroxyethyl)piperazine-1,4-diium dichloride), C23H31N3O+·2Cl−, is the dihydrochloride of a piperazine derivative bearing a bulky 3-(5H-dibenz[b,f]azepin-5-yl)propyl substituent. Protonation took place on both N atoms of the piperazine unit. The diazacyclohexane ring adopts a chair conformation. N—H...Cl, O—H...Cl and C—H...Cl hydrogen bonding as well as C—H...O contacts connect the components into a three-dimensional network in the crystal. Two C—H...π contacts are also observed.

The title compound, C10H12ClNO2, is a halogenated derivative of a secondary amide bearing an aromatic substituent. The C(=O)—N(H)—Car—Car torsion angle of −33.70 (18)° rules out the presence of resonance spanning the amide as well as the aromatic system. In the crystal, classical N—H...O hydrogen bonds, as well as C–H...O contacts connect the molecules into chains propagating along the a axis.

The title compound, C9H12NO2+·Cl−, is the hydrochloride of an N-substituted glycine derivative. The non-H atoms of the alkyl part of the molecule lie nearly in a plane (r.m.s. deviation of all fitted non-H atoms = 0.0142 Å). In the crystal structure, O—H...Cl, N—H...Cl and C—H...O hydrogen bonds involving both O atoms as well as C—H...Cl contacts connect the components of the title compound into a three-dimensional network.

The title compound (also known as 9-hydroxyrisperidone), C23H27FN4O3, is a heterocyclic compound with manifold pharmacological properties. The hydroxy group shows disorder over two positions, with site-occupancy factors of 0.856 (2) and 0.144 (2). The piperidine ring adopts a chair conformation, while the annulated ring bearing the hydroxy group is present in a half-chair conformation. Classical O—H...O hydrogen bonds as well as C—H...N contacts connect the molecules into undulating sheets lying perpendicular to the crystallographic b axis. The shortest centroid–centroid distance between two centers of gravity is 3.5867 (8) Å and is apparent between the benzoxazole moiety and the six-membered ring bearing the keto substituent.

The title compound, C30H28N6O2, is a symmetric diimine derived from ortho-dibenzaldehyde. Both C=N bonds are (E)-configured. The terminal N-bonded phenyl groups adopt staggered conformations relative to their respective parent heterocycles, the relevant least-squares planes intersect at angles of 32.35 (11) and 38.59 (10)°. In the crystal, C—H...O contacts connect the molecules into chains along the b axis and give rise to a C11(14)C11(14) and a R22(12) pattern on different levels of graph-set analysis. The shortest intercentroid distance between two centroids was found at 4.2074 (11) Å between the two five-membered heterocycles.

The title compound {systematic name: 4-[bis(4-fluorophenyl)methyl]piperazin-1-ium 2,4,6-trinitrophenolate}, C17H19F2N2+·C6H2N3O7−, is the picrate salt of a piperazine-supported amine bearing a benzhydryl substituent on one of its N atoms. During co-crystallisation, protonation took place on the N atom of the secondary amine functionality. The non-aromatic six-membered heterocycle adopts a chair conformation. In the crystal, N—H...O hydrogen bonds as well as C—H...O contacts connect the components into a three-dimensional network.

The asymmetric unit of the title salt, C17H19F2N2+.C15H13O2−, derived from a 1,4-diazacyclohexane derivative and a carboxylic acid, contains two formula units. The cation is protonated at the secondary amine functionality. The six-membered heterocycles adopt chair conformations. The fluorophenyl rings in the two cations make dihedral angles of 77.21 (19) and 78.8 (2)° while the aromatic rings in the anions enclose angles of 69.5 (2) and 69.9 (2)°. In the crystal, classical N—H...O hydrogen bonds as well as C—H...F and C—H...O contacts connect the entities into layers parallel to ac.

The molecule of the title pyridine derivative, C5H6N2O, shows approximate Cs symmetry. Intracyclic angles cover the range 118.34 (10)–123.11 (10)°. In the crystal, O—H...N, N—H...O and N—H...N hydrogen bonds connect the molecules into double layers perpendicular to the a axis. The shortest centroid–centroid distance between two π-systems is 3.8887 (7) Å.

The title compound, C12H14N5O2+·Br−, is the hydrobromide salt of a Schiff base in which protonation has taken place at the pyridine N atom. This organic cation is essentially planar (r.m.s. of all fitted non-H atoms = 0.0448 Å). In the crystal, N—H...Br hydrogen bonds as well as C—H...O and C–H...Br interactions connect the molecules, forming a three-dimensional network.

The title compound, C13H12N4O3, is an imidazole derivative featuring an annealed purine ring system. The benzimidazole-inspired moiety is essentially planar (r.m.s. of all fitted non-H atoms = 0.0205 Å). An intramolecular O—H...N hydrogen bond occurs. In the crystal, intermolecular N—H...O and C—H...O hydrogen bonds are observed, which connect the molecules into chains along [110]. The shortest centroid–centroid distance between two aromatic systems is 3.7771 (11) Å.

The title compound, C12H14N5O2+·Cl−·H2O, is the monohydrate of the hydrochloride of an oxopurine-derived Schiff base in which protonation took place at the pyridine N atom. The organic cation is essentially planar (r.m.s. of all fitted non-H atoms = 0.0373 Å). In the crystal, N—H...O and N—H...Cl hydrogen bonds as well as C—H...O and C—H...Cl contacts connect the different entities into a three-dimensional network. The shortest centroid–centroid distance between two pyrimidine rings is 3.6364 (9) Å.

In the title compound, C12H13N5O2, a Schiff-base-derived chelate ligand, the non-aromatic heterocycle and its substituents essentially occupy one common plane (r.m.s. of fitted non-H atoms = 0.0503 Å). The N=C bond is E-configured. Intracyclic angles in the pyridine moiety cover the range 117.6 (2)–124.1 (2)°. Intra- and intermolecular N—H...N and N—H...O hydrogen bonds are observed in the crystal structure, as are intra- and intermolecular C—H...O contacts which, in total, connect the molecules into a three-dimensional network. The shortest ring-centroid-to-ring-centroid distance of 3.5831 (14) Å is between the two different types of six-membered rings.

The cation of the title compound, C6H8NO2+·Cl−, is essentially planar (r.m.s. deviation = 0.0104 Å). Intermolecular O—H...Cl and N—H...Cl hydrogen bonds, as well as C—H...O contacts, connect the molecules in the crystal structure. A short C...C distance of only 3.3930 (19) Å between C atoms of neighbouring rings is indicative of π-stacking. The corresponding centroid–centroid distance between the two aromatic systems is 4.2370 (7) Å due to the small overlap of the adjacent rings.

The title compound, C15H14N4O2S, is a derivative of thioureadihydrazide. In contrast to the previously reported polymorph (orthorhombic, space group Pbca, Z = 8), the current study revealed monoclinic symmetry (space group P21/n, Z = 4). The molecule shows non-crystallographic C2 as well as approximate Cs symmetry. Intramolecular bifurcated O—H...(N,S) hydrogen bonds, are present. In the crystal, intermolecular N—H...S hydrogen bonds and C—H...π contacts connect the molecules into undulating chains along the b axis. The shortest centroid–centroid distance between two aromatic systems is 4.5285 (12) Å.

The title compound, C22H28N2, which is a double imine derived from ethane-1,2-diamine and mesityl aldehyde, has crystallographic inversion symmetry, with both C=N bonds E configured. The dihedral angle between the mesityl ring system and the imide functional group is 23.89 (17)°.

The molecule of the title pyridine derivative, C5H7N3, shows approximately non-crystallographic Cs symmetry. Intracyclic angles cover the range 117.50 (14)–123.03 (15)°. In the crystal, N—H...N hydrogen bonds connect molecules into a three-dimensional network. The closest intercentroid distance between two π-systems occurs with the c-axis repeat at 3.9064 (12) Å.