Metconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol, C17H22ClN3O, consisting of a cyclopentan-1-ol with 1,2,4-triazol-1-ylmethyl, gem-dimethyl and 4-chlorobenzyl groups attached at the 1-, 2- and 5-positions of the cyclopentanol ring. It has two stereocentres (cyclopentanol positions 1 and 5) leading to four stereoisomers, with the (1S,5R) form being the most bioactive. Despite its agricultural significance, detailed crystallographic data remain scarce. This study reports the crystal structure and Hirshfeld surface analysis of racemic cis-metconazole [(1S,5R)/(1R,5S)], determined in the monoclinic space group P21/c with two independent molecules in the asymmetric unit (Z′ = 2). Both exhibit similar conformations, with minor differences in the cyclopentanol ring puckering and the torsion angles between the three rings. The crystal packing consists of 21-screw-related hydrogen-bonded chains parallel to the b axis, with additional weak C—H...N and C—H...Cl contacts linking adjacent molecules. Hirshfeld surface analysis indicates that intermolecular interactions are dominated by contacts involving hydrogen (96.1 and 96.7% for the two molecules).

The crystal structure and a Hirshfeld-surface analysis of the chalcone derivative 1-(4-fluoro­phen­yl)-3,3-bis­(methyl­sulfan­yl)prop-2-en-1-one are presented.

A metabolite of the insecticide/acaricide etoxazole, designated R4 {systematic name N-[1-(4-tert-butyl-2-eth-oxy-phen-yl)-2-hy-droxy-eth-yl]-2,6-di-fluoro-benz-amide, C21H25F2NO3}, is presented. The mol-ecular structure has a central N-(2-hy-droxy-ethyl)formamide group flanked by 4-tert-butyl-2-eth-oxy-phenyl and 2,6-di-fluoro-phenyl-substituted rings. The overall conformation is defined by its torsional degrees of freedom [N-C-C-C = 56.09 (18) and 99.41 (18)°], which place the 4-tert-butyl-2-eth-oxy-phenyl and 2,6-di-fluoro-phenyl rings at a dihedral angle of 70.66 (5)°. In the crystal, mol-ecules are linked by a strong O-H-O hydrogen bond into chains that extend parallel to the a-axis. There are also weaker C-H-F and π-stacking [centroid-centroid distance = 4.266 (2) Å] inter-actions. A Hirshfeld surface analysis reveals that the inter-molecular contacts are dominated by inter-actions involving hydrogen, the most abundant being H⋯H (54.1%), H⋯O/O⋯H (13.0%), H⋯F/F⋯H (12.8%), and H⋯C/C⋯H (12.8%).

Etoxazole (C21H23F2NO2), systematic name 4-(4-tert-butyl-2-ethoxyphenyl)-2-(2,6-difluorophenyl)-4,5-dihydro-1,3-oxazole, is a fluorinated insecticide and acaricide that inhibits chitin biosynthesis, disrupting insect development by preventing proper exoskeleton formation. Widely used in agriculture since 1998, it is readily absorbed by plant tissues and translocates within leaves. Metabolic studies have identified several oxidative degradation products, while toxicological assessments have examined potential effects, including oxidative stress. This study presents a detailed crystallographic and Hirshfeld surface analysis of etoxazole. The molecule consists of a central dihydro-oxazole ring flanked by 2,6-difluorophenyl and 4-tert-butyl-2-ethoxyphenyl groups, each twisted relative to the oxazole core. The dihydro-oxazole ring is nearly planar, with the substituted phenyl rings forming dihedral angles of 44.20 (4)° and 47.87 (4)° with the mean plane of the dihydro-oxazole. The ethoxy group exhibits a dihedral angle of 15.04 (11)° to the tert-butylphenyl ring, while the tert-butyl group itself shows minor torsional disorder [major:minor occupancies are 0.760 (6):0.240 (6)]. The molecular packing is dominated by van der Waals-type interactions, though weak C—H...F and C—H...O interactions lead to pleated layers parallel to the ab plane, which further stack along the c-axis direction. A Hirshfeld surface analysis confirms the prevalence of van der Waals interactions in crystal stabilization.

The title compound, C11H11FOS2, is a fluorinated chalcone derivative with potential applications in medicinal chemistry and functional materials. The molecular structure includes a planar 4-fluorophenyl ring linked by a carbonyl group and an ethenyl spacer to an approximately planar bis(methylsulfanyl) moiety (r.m.s. deviations from planarity are 0.0106 and 0.0315 Å, respectively). These planar groups are twisted relative to each other, subtending a dihedral angle of 32.23 (4)°. The crystal packing lacks classical hydrogen bonds or aromatic π-stacking, but molecules are connected through weaker C—H...O and C—H...S contacts into layers parallel to the ab plane and tapes extending along the b-axis direction. The 4-fluorophenyl groups on adjacent tapes interdigitate. Hirshfeld surface analysis shows that the majority (>90%) of intermolecular contacts involve hydrogen atoms.

In the present study, disulfonamides piperazine derivatives were synthesized by Hinsberg reaction of various sulfonyl chlorides with 2-(piperazin-1-yl)ethanamine and evaluation their cell proliferation activity. All the synthesized compounds were characterized by 1H, 13C NMR, mass spectrometry and X-ray crystallographic techniques. X-ray diffraction studies revealed that the central piperazine ring and two terminal substituted sulfonyl phenyl rings joined by sulfonamide linkage are present in every structure. The cell proliferation activity of synthesized compounds was measured on human buccal mucosa oral fibroblast primary cell lines. Among the synthesized compounds, 4-nitro-N-(2-4-[(4-nitrophenyl)sulfonyl]piperazin-1-ylethyl)benzenesulfonamide, 4-(trifluoromethyl)-N-[2-(4-[4-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl)ethyl]benzenesulfonamide and 2-nitro-N-(2-4-[(2-nitrophenyl)sulfonyl]piperazin-1-ylethyl)benzenesulfonamide showed potential activity against tested cell lines.

This study presents the synthesis, crystal structure, and a Hirshfeld-surface analysis of the bioactive compound 5-methyl-1H-pyrazol-3-yl 4-nitrobenzenesulfonate(C10H9N3O5S), a pyrazole derivative with pharmacological potential. Pyrazoles are known for diverse bioactivities, and recent research emphasizes their role as a 'privileged structure' in drug design. Here, the asymmetric unit of the title compound contains two distinct molecules, A and B, exhibiting differences in conformation resulting from variation in key torsion angles. These distinctions influence the molecular orientation and intermolecular interactions, with strong N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds forming a centrosymmetric tetramer stabilized by pi-pi stacking. Hirshfeld surface analysis readily confirms differing intermolecular contacts for A and B, primarily involving hydrogen atoms and differences in their close contacts to nitrogen and oxygen. This study offers further insight into the molecular architecture and potential interactions of pyrazole-based drug candidates.

The etoxazole metabolite R13, systematic name 4-(4-tert-butyl-2-ethoxyphenyl)-2-(2,6-difluorophenyl)oxazole (C21H21F2NO2), results from the oxidation of etoxazole, a chitin synthesis inhibitor belonging to the oxazoline class, widely used as an insecticide/acaricide since 1998. The structure of R13 features a central oxazole ring with attached 2,6-difluorophenyl and 4-t-butyl-2-ethoxyphenyl moieties. The overall conformation gives dihedral angles between these rings and the oxazole of 24.91 (5)° (with difluorophenyl) and 15.30 (6)° (with t-butyl-ethoxyphenyl), indicating an overall deviation from planarity. Additionally, torsion angles of the ethoxy and t-butyl groups define the orientation of these substituents relative to their benzene ring. In the crystal packing, no significant hydrogen bonds are present, but a Hirshfeld surface analysis highlights weak intermolecular contacts leading to π–π-stacked dimers linked by weak C—H...N contacts. The packing analysis confirms that most intermolecular interactions involve hydrogen atoms.

The electrical and vibrational properties of Trimipraminium maleate (TPM) are reported experimentally and theoretically. Vibrational spectra were recorded, and theoretical wavenumbers were determined and assigned using potential energy distribution. The intra-molecular hydrogen bonding O-H center dot center dot center dot O interaction in maleate is reflected by Hirshfeld surfaces. A small energy gap explains a possible charge transfer via N-H center dot center dot center dot O intermolecular interaction. MD simulations studies were carried out for the TPM at varying temperatures 300, 310, 320, and 330K in three different solvents (water, DMSO, and methanol). Non-covalent interactions are implied from the QTAIM analysis.

The low-temperature crystal structures of four organic salts of the anti-spasmodic drug trihexyphenidyl are presented.

Syntheses and X-ray crystal structures of four 4-(4-meth-oxy-phen-yl)piperazin-1-ium (MeOPP) salts, with 2,2,2-tri-fluoro-acetate, C11H17N2O+·C2F3O2 - (I), 2,3,4,5,6-penta-fluoro-benzoate, C11H17N2O+·C7F5O2 -·H2O (II), 4-iodo-benzoate C11H17N2O+·C7H4IO2 -·H2O (III), and 4-methyl-benzoate, C11H17N2O+·C8H7O2 -·H2O (IV) anions are presented. The salts form directly from equimolar qu-anti-ties of N-(4-meth-oxy-phen-yl)piperazine and the corresponding organic acid in methanol and crystallize from 1:1 methanol/ethyl acetate. Salt I is anhydrous whereas II, III, and IV are all monohydrates. In all cases, the MeOPP cation conformation is determined by the torsion about the N-C bond between the piperazinium and 4-meth-oxy-benzene rings. Crystal packing in each structure is largely dictated by N-H⋯O and (in II, III, and IV) O-H⋯O hydrogen bonds, although each also features weak C-H⋯O-type hydrogen bonds. Salt II also has π-π-stacking inter-actions between cation and anion arene rings, and III exhibits I⋯I close contacts.

The synthesis and crystal structure of C3HF3N2OS, systematic name 5-(trifluoromethyl)-1,3,4-thiadiazol-2(3H)-one (5-TMD-2-one), a compound containing the pharmacologically important heterocycle 1,3,4-thiadiazole, is presented. The asymmetric unit comprises six independent molecules (Z′ = 6), all of which are planar. The r.m.s. deviations from each mean plane range from 0.0063 to 0.0381 Å, not including the CF3 fluorine atoms. Within the crystal, two of the molecules form hydrogen-bonded dimers that in turn combine with inversion-related copies to form tetrameric constructs. Similar tetramers, but lacking inversion symmetry, are formed by the remaining four molecules. The tetramers are linked into tape-like motifs by S...O and O...O close contacts. The environments of each symmetry-independent molecule were compared via a Hirshfeld surface analysis. The most abundant atom–atom contacts are between fluorine atoms, while the strongest result from N—H...O hydrogen bonds.

The syntheses and crystal structures are presented for four organic salts of the 4-(4-nitro-phen-yl)piperazinium cation, namely, 4-(4-nitro-phen-yl)piperazinium hydrogen succinate, C10H14N3O2+·C4H5O4- (I), 4-(4-nitro-phen-yl)piperazinium 4-amino-benzoate monohydrate, C10H14N3O2+·C7H6NO2-·H2O (II), 4-(4-nitro-phen-yl)piperazinium 2-(4-chloro-phen-yl)acetate, C10H14N3O2+·C8H6ClO2- (III) and 4-(4-nitro-phen-yl)piperazinium 2,3,4,5,6-penta-fluoro-benzoate, C10H14N3O2+·C7F5O2- (IV). The salts form from mixtures of N-(4-nitro-phen-yl)piperazine and the corresponding acid [succinic acid (I), 4-amino-benzoic acid (II), 2-(4-chloro-phen-yl)acetic acid (III) and 2,3,4,5,6-penta-fluoro-benzoic acid (IV)] in mixed solvents of methanol and ethyl acetate. Salts I, III, and IV are anhydrous, whereas II is a monohydrate. In each structure, the overall conformation of the cation is determined by the disposition of the exocyclic N-C bond of the piperazine ring (either axial or equatorial) and twists about the N-C bond between the piperazine ring and its attached 4-nitro-phenyl ring. The packing motifs in each structure are quite different, though all are dominated by strong N-H⋯O hydrogen bonds, which are augmented in I and II by O-H⋯O hydrogen bonds, and in III by a π-π stacking inter-action between inversion-related 4-nitro-phenyl groups.

The crystal structures and Hirshfeld surface analyses of three salts of 1-(4-nitrophenyl)piperazine with 2-chlorobenzoic acid, 2-bromobenzoic acid and 2-iodobenzoic acid are reported. The chlorobenzoate salt, C10H14N3O2 +·C7H4ClO2 −, contains whole-ion-disordered cations and anions, which were modeled with two equivalent conformations with occupancies of 0.745 (10)/0.255 (10) and 0.563 (13)/0.437 (13), respectively. The bromobenzoate and iodobenzoate derivatives are isomorphous and crystallize as hemihydrates, viz. C10H14N3O2 +·C7H4BrO2 −·0.5H2O and C10H14N3O2 +·C7H4IO2 −·0.5H2O, respectively [the water molecule is disordered over two locations with occupancies of 0.276 (3)/0.223 (3) for the iodobenzoate derivative]. In the extended structures, all three salts feature an R 4 4(12) loop of two anions and two cations linked by N—H...O hydrogen bonds.

A simple and efficient fluorescent probe ( E )-4-bromo-2-((((5-methylfuran-2-yl)methyl)imino)methyl)phenol (BFMP) for the detection of Zn 2+ ions was synthesized by the condensation of 5-methyl-furfurylamine and 5-bromosalicylaldehyde.

The synthesis and crystal structures of the mol-ecular salts of 4-(4-nitro-phen-yl)piperazine with tri-fluoro-acetate, namely, 4-(4-nitro-phen-yl)piperazin-1-ium tri-fluoro-acetate, C10H14N3O2 +·C2F3O2 - (I), and with tri-chloro-acetate, namely, 4-(4-nitro-phen-yl)piperazin-1-ium tri-chloro-acetate, C10H14N3O2 +·C2Cl3O2 -, (II), are reported and compared. A partial positional disorder of the anions was found. In both structures, the piperazine rings adopt a chair conformation, whereas the positions of the nitro-phenyl group on the piperazine ring differ from bis-ectional in (I) to equatorial in (II). In both structures, the supra-molecular assemblies are mono-periodic on the basis of the chain-of-rings motifs supported by aromatic π-π inter-actions. Hirshfeld surface analysis was used to explore the inter-molecular close contacts in both crystals. The most dominant contacts of the Hirshfeld surface of the cation-anion pairs of the asymmetric units are O⋯H/H⋯O, and those with a contribution of halogen atoms: F⋯H/H⋯F in (I) and Cl⋯H/H⋯Cl in (II), respectively.

The crystal structure of ethiprole {systematic name: 5-amino-1-[2,6-di-chloro-4-(tri-fluoro-meth-yl)phen-yl]-4-ethane-sulfinyl-1H-imidazole-3-carbo-nitrile}, C13H9Cl2F3N4OS, a phenyl-pyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: an N-bound 2,6-di-chloro-4-tri-fluoro-methyl-phenyl ring and C-bound amine, ethane-sulfinyl, and cyano groups. The sulfur atom of the ethane-sulfinyl group is trigonal-pyramidal and stereogenic. The structure exhibits whole-mol-ecule configurational disorder due to superposition of enanti-omers. The crystal packing is dominated by strong N-H⋯O and N-H⋯N hydrogen bonds, which form R 4 4(18) and R 2 2(12) ring motifs. Since the ethiprole mol-ecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid mol-ecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.

The synthesis and crystal structure of a monoclinic polymorph of 2-amino-5-chlorobenzophenone oxime, C13H11ClN2O, are presented. The molecular conformation results from twisting of the phenyl and 2-amino-5-chloro benzene rings attached to the oxime group, which subtend a dihedral angle of 80.53 (4)°. In the crystal, centrosymmetric dimers are formed as a result of pairs of strong O—H...N hydrogen bonds. A comparison is made to a previously known triclinic polymorph, including differences in atom–atom contacts obtained via a Hirshfeld-surface analysis.

The crystal structure and a Hirshfeld surface analysis of the substituted anilinium salt 4-(dimethylazaniumyl)-2-hydroxyanilinium dichloride monohydrate, C8H14N2O+·2Cl−·H2O, at low temperature (90 K) are presented. The organic cation is essentially planar: the r.m.s. deviation of its non-hydrogen atoms (aside from the two methyl groups) is 0.0045 Å. The methyl carbons are 1.3125 (12) Å and 1.1278 (12) Å either side of the mean plane. The crystal packing involves extensive hydrogen bonding of types O—H...Cl, N—H...Cl, N—H...OW, and OW—HW...Cl (where W = water), which arrange into chains of R24(12) motifs that combine to form corrugated layers parallel to (10\overline{1}). Atom–atom contacts for the cation primarily involve hydrogen, leading to the most abundant coverage percentages being 51.3% (H...H), 23.0% (H...Cl), 12.9% (H...O), and 9.7% (C...H).

The syntheses and crystal structures of four salts of amitriptynol (C20H25NO) with different carb-oxy-lic acids are described. The salts formed directly from solutions of amitriptyline (which first hydrolysed to amitriptynol) and the cor-responding acid in aceto-nitrile to form amitriptynolium [sys-tem-atic name: (3-{2-hy-droxy-tri-cy-clo[9.4.0.03,8]penta-deca-1(11),3,5,7,12,14-hexa-en-2-yl}pro-pyl)di-methyl-az-an-ium] 4-meth-oxy-benzoate monohydrate, C20H26NO+·C8H7O3 -·H2O, (I), ami-triptynolium 3,4-di-meth-oxy-benzoate trihydrate, C20H26NO+·C9H9O4 -·3H2O, (II), amitriptynolium 2-chloro-benzoate, C20H26NO+·C7H4ClO2 -, (III), and amitriptynolium thio-phene-2-carboxyl-ate monohydrate, C20H26NO+·C5H3O2S-·H2O, (IV). Compound (III) crystallizes with two cations, two anions and six water mol-ecules in the asymmetric unit. The different conformations of the amitriptynolium cations are determined by the torsion angles in the di-methyl-amino-propyl chains and the -CH2-CH2- bridge between the benzene rings in the tricyclic ring system, and are complicated by disorder of the bridging unit in II and III. The packing in all four salts is dominated by N-H⋯O and O-H⋯O hydrogen bonds. Hirshfeld surface analyses show that the amitriptynolium cations make similar inter-species contacts, despite the distinctly different packing in each salt.