Crystal structures of four organic salts of trihexyphenidyl at 90†K.

The syntheses and crystal structure studies of four organic salts of trihexyphenidyl, viz., trihexyphenidylium [1-(3-cyclo-hexyl-3-hy-droxy-3-phenyl-prop-yl)piperidin-1-ium] 4-nitro-benzoate, C20H32NO+·C7H4NO4 - (I), trihexyphenidylium 4-hy-droxy-benzoate, C20H32NO+·C7H5O- (II), trihexyphenidylium 4-bromo-benzoate, C20H32NO+·C7H4BrO2 - (III), and trihexyphenidylium thio-phene-2-carboxyl-ate hemihydrate, 2C20H32NO+·2C5H3O2S-·H2O (IV), con-ducted at 90 K are described. Structures I, II, and III are solvent free with one cation-anion pair per asymmetric unit, while IV crystallizes as a hemihydrate, having two cation-anion pairs and one water of crystallization in its asymmetric unit. Structures I and III exhibit configurational disorder of the cation. Structure IV also exhibits disorder, but only of the thio-phene-2-carboxyl-ate anions. Structure II is a non-merohedric twin by a twofold rotation about [403]. The main supra-molecular motifs in I, II, and III are similar R 2 2(10) rings between cation-anion pairs, although their packing within the crystals is distinct. As a consequence of having two cation-anion pairs and a water mol-ecule in its asymmetric unit, the packing in IV is by far the most complex of the four structures, its hydrogen-bonding patterns being quite different from I, II, or III. In all the crystals studied, N-H⋯O, O-H⋯O, and C-H⋯O inter-actions are observed, plus C-H⋯Br close contacts for III.

The synthesis, crystal structure and spectroscopic analysis of (E)-3-(4-chloro-phen-yl)-1-(2,3-di-hydro-benzo[b][1,4]dioxin-6-yl)prop-2-en-1-one.

The synthesis, crystal structure and spectroscopic analysis of (E)-1-(2,3-di-hydro-benzo[b][1,4]dioxin-6-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one (C17H13ClO3), a substituted chalcone, are described. The overall geometry of the mol-ecule is largely planar (r.m.s. deviation = 0.1742 Å), but slightly kinked, leading to a dihedral angle between the planes of the benzene rings at either side of the mol-ecule of 8.31 (9)°. In the crystal, only weak inter-actions determine the packing motifs. These include C-H⋯O and C-H⋯Cl hydrogen bonds and π-π overlap of aromatic rings.

Crystal structure and Hirshfeld-surface analysis of a monoclinic polymorph of 2-amino-5-chloro-benzo-phenone oxime at 90†K.

The synthesis and crystal structure of a monoclinic polymorph of 2-amino-5-chloro-benzo-phenone oxime, C13H11ClN2O, are presented. The mol-ecular 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.

Synthesis and crystal structure studies of 5-(tri-fluoro-meth-yl)-1,3,4-thia-diazol-2(3H)-one at 180†K.

The synthesis and crystal structure of C3HF3N2OS, systematic name 5-(tri-fluoro-meth-yl)-1,3,4-thia-diazol-2(3H)-one (5-TMD-2-one), a compound containing the pharmacologically important heterocycle 1,3,4-thia-diazole, is presented. The asymmetric unit comprises six independent mol-ecules (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 mol-ecules form hydrogen-bonded dimers that in turn combine with inversion-related copies to form tetra-meric constructs. Similar tetra-mers, but lacking inversion symmetry, are formed by the remaining four mol-ecules. The tetra-mers are linked into tape-like motifs by S⋯O and O⋯O close contacts. The environments of each symmetry-independent mol-ecule 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.

Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro-phen-yl)-N-isopropyl-2-(methyl-sulfon-yl)acetamide.

The synthesis and crystal structure of the title compound, C12H16FNO3S, which is related to the herbicide flufenacet, are presented. The dihedral angle between the amide group and the fluorinated benzene ring is 87.30 (5)° and the N-C-C-S torsion angle defining the orientation of the methyl-sulfonyl substituent relative to the amide group is 106.91 (11)°. In the crystal, inversion-related mol-ecules form dimers as a result of pairwise C-H⋯O hydrogen bonds, which appear to be reinforced by short O⋯π contacts [O⋯Cg = 3.0643 (11) Å]. A Hirshfeld surface analysis was used to qu-antify the various types of inter-molecular contacts, which are dominated by H atoms.

Syntheses, crystal structures and Hirshfeld surface analyses of four mol-ecular salts of amitriptynol.

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.

Syntheses and crystal structures of four 4-(4-meth-oxy-phen-yl)piperazin-1-ium salts: tri-fluoro-acetate, 2,3,4,5,6-penta-fluoro-benzoate, 4-iodo-benzoate, and a polymorph with 4-methyl-benzoate.

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.

Syntheses and crystal structures of four 4-(4-nitro-phen-yl)piperazinium salts with hydrogen succinate, 4-amino-benzoate, 2-(4-chloro-phen-yl)acetate and 2,3,4,5,6-penta-fluoro-benzoate anions.

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.

Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS): a case study of whole-mol-ecule configurational disorder.

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.

3-(3-Nitro-phen-yl)-1-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one.

The structure of the title compound, C18H13NO4, shows that the whole mol-ecule is almost planar but with a dihedral angle between the two phenyl rings of 19.22 (5)°. The mol-ecules are linked by C-H⋯O inter-actions, forming sheets in the (21) plane.

Syntheses and crystal structures of benzyl N'-[(E)-2-hydroxybenzylidene]hydrazinecarboxylate and benzyl N'-[(E)-5-bromo-2-hydroxybenzylidene]hydrazinecarboxylate.

Benzyl N'-[(E)-2-hydroxybenzylidene]hydrazinecarboxylate, C15H14N2O3 (I) and benzyl N'-[(E)-5-bromo-2-hydroxybenzylidene]hydrazinecarboxylate (II), C15H13BrN2O3, have been synthesized by the reaction of either 2-hy-droxy-benzaldehyde or 5-bromo-2-hy-droxy-benzaldehyde with benzyl carbazate, respectively. Both the compounds crystallize in the monoclinic crystal system with space groups Pn (Z' = 1, I) and P21/c (Z' = 2, II). Mol-ecular conformations in each structure are similar, and both structures feature strong intra-molecular O-H⋯N hydrogen bonds, which form S(6) ring motifs. There are also strong N-H⋯O and weak C-H⋯O hydrogen bonds in both structures, but their modes of packing within their respective crystals are markedly different. Some comparisons are made with the structures of a few related compounds.