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The title compound, C16H11N2OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intramolecular N—H...O hydrogen bond occurs between the imino and carbonyl groups. In the crystal, the molecules are linked into inversion dimers by C—H...O interactions. Aromatic π–π stacking between the naphthalene ring systems lead to the formation of chains along [001]. A Hirshfeld surface analysis was undertaken to investigate and quantify the intermolecular interactions. In addition, energy frameworks were used to examine the cooperative effect of these intermolecular interactions across the crystal, showing dispersion energy to be the most influential factor in the crystal organization of the compound.

The title compound, C32H28F2N2O2, a highly functionalized tetrahydropyridine, was synthesized by a one-pot multi-component reaction of 4-fluoroaniline, ethyl acetoacetate and benzaldehyde at room temperature using sodium lauryl sulfate as a catalyst. The compound crystallizes with two molecules in the asymmetric unit. The tetrahydropyridine ring adopts a distorted boat conformation in both molecules and the dihedral angles between the planes of the fluoro-substituted rings are 77.1 (6) and 77.3 (6)°. The amino group and carbonyl O atom are involved in an intramolecular N—H...O hydrogen bond, thereby generating an S(6) ring motif. In the crystal, molecules are linked by C—H...F hydrogen bonds forming a three-dimensional network and C—H...π interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (47.9%), C...H/H...C (30.7%) and F...H/H...F (12.4%) contacts. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311+G(2d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was used to determine the energy gap and the Natural Bond Orbital (NBO) analysis was done to study donor–acceptor interconnections.

Creatinine, a biologically important compound, is used to analyze kidney function and kidney diseases in the human body. The salt form of creatinine is used in the formation of drug materials like anti‐HIV, antifungal, antiprotozoal, antiviral and antitumour compounds. Here we report the solid‐state structures of three new crystalline salts, namely, creatininium (2‐amino‐1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐3‐ium) bromide, C4H8N3O+·Br−, (I), creatininium 3‐aminobenzoate, C4H8N3O+·C7H6NO2−, (II), and creatininium 3,5‐dinitrobenzoate, C4H8N3O+·C7H3N2O6−, (III). These salts have been synthesized and characterized by single‐crystal X‐ray diffraction and Hirshfeld surface analysis. The structural chemistry of salts (I)–(III) and their crystal packing are discussed in detail. The primary interaction between the creatinine cation and the acid anion in the three salts is N—H...Br/O hydrogen bonds. In salt (I), the creatinine cation and bromide anion are connected through a pair of N—H...Br hydrogen bonds forming R42(8) and R42(12) ring motifs. In salts (II) and (III), the creatinine cation interacts with the corresponding anion via a pair of N—H...O hydrogen bonds. The crystal structure is further stabilized by C—H...O and O—H...O hydrogen bonds with the ring motifs R22(8), R21(7) and R21(6). Furthermore, the crystal structures are stabilized by π–π, C—H...π, C—O...π and N—O...π stacking interactions. The contributions made by each hydrogen bond in maintaining the crystal structure stability has been quantified by Hirshfeld surface analysis. [ABSTRACT FROM AUTHOR]

Two new crystalline solids, namely, 5‐aminotetrazole–3,5‐dihydroxybenzoic acid–water (1/4/6), CH3N5·4C7H6O4·6H2O (I), and 5‐aminotetrazolium 3,5‐dinitrosalicylate, CH4N5+·C7H3N2O7− (II), have been synthesized and characterized by single‐crystal X‐ray diffraction and Hirshfeld surface analysis. The crystal packing arrangements of I and II are governed by N—H...O and O—H...O hydrogen‐bonding interactions. In cocrystal I, adjacent acid molecules are linked through O—H...O hydrogen bonds, forming a dimer with an R22(8) motif. In salt II, the tetrazolium cation and acid anion are linked through N—H...O hydrogen bonds to also form a dimer with an R22(8) motif. Further N—H...O and O—H...O hydrogen bonds help to stabilize the crystal packing, along with aromatic π–π stacking interactions in I and carbonyl...π interactions in II. The Hirshfeld surface analysis and fingerprint plots reveal that O...H/H...O interactions contribute 34.4% of the total interactions in the crystal packing of cocrystal I and 36.7% in salt II. [ABSTRACT FROM AUTHOR]

In the title compound, C20H13NO2S2, the carbazole ring system forms a dihedral angle of 89.08 (1)° with the sulfonyl-substituted phenyl ring. Intramolecular C—H...O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S(6) rings. In the crystal, molecules are linked via pairs of C—H...O hydrogen bonds forming inversion dimers with an R22(12) graph-set motif. Analysis of the Hirshfeld surfaces and two-dimensional fingerprint plots was used to explore the distribution of weak intermolecular interactions in the crystal structure.

The title compound, C 16 H 11 N 2 OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intra-molecular N-H⋯O hydrogen bond occurs between the imino and carbonyl groups. In the crystal, the mol-ecules are linked into inversion dimers by C-H⋯O inter-actions. Aromatic π-π stacking between the naphthalene ring systems lead to the formation of chains along [001]. A Hirshfeld surface analysis was undertaken to investigate and qu-antify the inter-molecular inter-actions. In addition, energy frameworks were used to examine the cooperative effect of these inter-molecular inter-actions across the crystal, showing dispersion energy to be the most influential factor in the crystal organization of the compound., (© Akkache et al. 2024.)

In the title compound, C20H13NO2S2, the carbazole ring system forms a dihedral angle of 89.08 (1)° with the sulfonyl-substituted phenyl ring. Intramolecular C--H...O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S(6) rings. In the crystal, molecules are linked via pairs of C--H...O hydrogen bonds forming inversion dimers with an R2²(12) graph-set motif. Analysis of the Hirshfeld surfaces and two-dimensional fingerprint plots was used to explore the distribution of weak intermolecular interactions in the crystal structure. [ABSTRACT FROM AUTHOR]

In the title compound, C12H13Cl2NO2, the piperidine ring adopts a chair conformation. The dihedral angle between the mean plane of the piperidine ring and the benzene ring is 58.5 (3)°. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by C—H...O hydrogen bonds, forming undulating sheets parallel to the ab plane. The C atoms of the hydroxypiperidine ring are disordered over two sets of sites with refined occupancies of 0.545 (7) and 0.455 (7). The intermolecular interactions in the crystal structure were quantified using Hirshfeld surface analysis.

The title com-pound, C 32 H 28 F 2 N 2 O 2 , a highly functionalized tetra-hydro-pyridine, was synthesized by a one-pot multi-com-ponent reaction of 4-fluoro-aniline, ethyl aceto-acetate and benzaldehyde at room temperature using sodium lauryl sulfate as a catalyst. The com-pound crystallizes with two mol-ecules in the asymmetric unit. The tetra-hydro-pyridine ring adopts a distorted boat conformation in both mol-ecules and the dihedral angles between the planes of the fluoro-substituted rings are 77.1 (6) and 77.3 (6)°. The amino group and carbonyl O atom are involved in an intra-molecular N-H⋯O hydrogen bond, thereby generating an S (6) ring motif. In the crystal, mol-ecules are linked by C-H⋯F hydrogen bonds forming a three-dimensional network and C-H⋯π inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (47.9%), C⋯H/H⋯C (30.7%) and F⋯H/H⋯F (12.4%) contacts. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311+G(2d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was used to determine the energy gap and the Natural Bond Orbital (NBO) analysis was done to study donor-acceptor interconnections., (© Bansal et al. 2023.)

Hirshfeld surfaces and two-dimensional fingerprint plots are used to analyse the intermolecular interactions in two new phosphorothioic triamide structures, namely N, N′, N′′-tris(3,4-dimethylphenyl)phosphorothioic triamide acetonitrile hemisolvate, P(S)[NHC6H3-3,4-(CH3)2]3·0.5CH3CN or C24H30N3PS·0.5CH3CN, (I), and N, N′, N′′-tris(4-methylphenyl)phosphorothioic triamide-3-methylpiperidinium chloride (1/1), P(S)[NHC6H4(4-CH3)]3·[3-CH3-C5H9NH2]+·Cl− or C21H24N3PS·C6H14N+·Cl−, (II). The asymmetric unit of (I) consists of two independent phosphorothioic triamide molecules and one acetonitrile solvent molecule, whereas for (II), the asymmetric unit is composed of three components (molecule, cation and anion). In the structure of (I), the different components are organized into a six-molecule aggregate through N-H...S and N-H...N hydrogen bonds. The components of (II) are aggregated into a two-dimensional array through N-H...S and N-H...Cl hydrogen bonds. Moreover, interesting features of packing arise in this structure due to the presence of a double hydrogen-bond acceptor (the S atom of the phosphorothioic triamide molecule) and of a double hydrogen-bond donor (the N-H unit of the cation). For both (I) and (II), the full fingerprint plot of each component is asymmetric as a consequence of the presence of three fragments. These analyses reveal that H...H interactions [67.7 and 64.3% for the two symmetry-independent phosphorothioic triamide molecules of (I), 30.7% for the acetonitrile solvent of (I), 63.8% in the phosphorothioic triamide molecule of (II) and 62.9% in the 3-methylpiperidinium cation of (II)] outnumber the other contacts for all the components in both structures, except for the chloride anion of (II), which only receives the Cl...H contact. The phosphorothioic triamide molecules of both structures include unsaturated C atoms, thus presenting C...H/H...C interactions: 17.6 and 21% for the two symmetry-independent phosphorothioic triamide molecules in (I), and 22.7% for the phosphorothioic triamide molecule of (II). Furthermore, the N-H...S hydrogen bonds in both (I) and (II), and the N-H...Cl hydrogen bonds in (II), are the most prominent interactions, appearing as large red spots on the Hirshfeld surface maps. The N...H/H...N contacts in structure (I) are considerable, whereas for (II), they give a negligible contribution to the total interactions in the system. [ABSTRACT FROM AUTHOR]

In the title compound, C 20 H 13 NO 2 S 2 , the carbazole ring system forms a dihedral angle of 89.08 (1)° with the sulfonyl-substituted phenyl ring. Intra-molecular C-H⋯O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S (6) rings. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds forming inversion dimers with an R 2 2 (12) graph-set motif. Analysis of the Hirshfeld surfaces and two-dimensional fingerprint plots was used to explore the distribution of weak inter-molecular inter-actions in the crystal structure.