A very short O—H···O hydrogen bond in the structure of clozapinium hydrogen bis­­(3,5-di­nitro­benzoate)

Funding: HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.In the title salt {systematic name: 4-[6-chloro-2,9-di­aza­tri­cyclo­[9.4.0.03,8]penta­deca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methyl­piperazin-1-ium 3,5-di­nitro­benzoate–3,5-di­nitro­benzic acid (1/1)}, C18H20ClN4+·C7H3N2O6−·C7H4N2O6, there is a very short, asymmetric, O—H···O hydrogen bond [O···O = 2.453 (3) Å] within the anion. The oxygen atoms of one of the nitro groups of the anion are disordered over two sets of sites having occupancies of 0.56 (3) and 0.44 (3). The fused tricyclic portion of the cation adopts a butterfly conformation, with a dihedral angle of 45.59 (6)° between the planes of the two aryl rings. In the crystal, a combination of O—H···O, N—H⋯O and C—H···O hydrogen bonds links the component species into a three-dimensional framework. Comparisons are made with the structures of some related compounds.Publisher PDFPeer reviewe

Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate

The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C21H24NO3+·C6H2N3O7- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H···(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H···O hydrogen bonds to form sheets. Comparisons are made with some related structures.Publisher PDFPeer reviewe

Crystal structure of ebastinium 3,5-dinitrobenzoate

BKS thanks the UGC for the award of a Rajiv Gandhi National Fellowship.Ebastine, 4-(benzhydryloxy)-1-[4-(4-tert-butylphenyl)-4-oxobutyl]piperidine, reacts with 3,5-dinitrobenzoic acid in methanol solution to give the title 1:1 salt, ebastinium 3,5-dinitrobenzoate, C32H40NO2+·C7H3N2O6-. In the cation, the disubstituted aryl ring exhibits orientational disorder over two sets of atomic sites having occupancies 0.706(4) and 0.294(6), with a dihedral angle of 41.2(5)° between the two orientations: the bulky Ph2CH—O– substituent occupies an axial site on the piperidine ring. The two ions in the selected asymmetric unit are linked by a nearly linear N—H···O hydrogen bond and this, in combination with two C—H···O hydrogen bonds, links the ions into complex sheets.Publisher PDFPeer reviewe

Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.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—Hπ(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.Publisher PDFPeer reviewe

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates : a robust R_2^2(8) supramolecular motif (even when disordered)

Acknowledgements MAES thanks the University of Mysore for provision of research facilities. Funding information HSY thanks UGC for the award of a UGC–BSR Faculty Fellowship for three years. BKS thanks the UGC for the award of a Rajeev Gandhi fellowship.Peer reviewedPublisher PD

Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents : a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene

HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.Co-crystallization of racemic 1-cyclo­hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenid­yl) with 3,5-di­nitro­benzoic acid gives a simple 1:1 salt, namely 1-(3-cyclo­hexyl-3-hy­droxy-3-phenyl­prop­yl)piperidin-1-ium 3,5-di­nitro­benzoate, C20H 32NO +·C 7H 3N 2O 6 −, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-aminium hydrogen bis­(3,5-di­nitro­benzoate), C18H 19ClNS +·[H(C 7H 3N 2O 6) 2] −, (II), the anion of which contains a very short O—H⋯O hydrogen bond, with dimensions O—H = 1.04 (3) Å, H⋯O = 1.41 (3) Å, O⋯O = 2.4197 (15) Å and O—H⋯O = 161 (3)°. In the cation of (I), the cyclo­hexyl and piperidyl rings both adopt chair conformations, whereas in the cation of (II), the central heterocyclic ring adopts a boat conformation, so that the dihedral angle between the two aryl rings is 41.56 (4)°. A combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions of (I) into a complex chain of rings, and these chains are linked into sheets by π– π stacking inter­actions between inversion-related pairs of anions. In compound (II), a different combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions into sheets. Comparisons are made with some related structures.Publisher PDFPeer reviewe

Two isostructural 3-(5-ar­yl­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-ones: disorder and supra­molecular assembly

Two new chalcones containing both pyrazole and thio­phene substituents have been prepared and structurally characterized. 3-(3-Methyl-5-phen­oxy-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-one, C23H18N2O2S (I), and 3-[3-methyl-5-(2-methyl­phen­oxy)-1-phenyl-1H-pyrazol-4-yl]-1-(thio­phen-2-yl)prop-2-en-1-one, C24H20N2O2S (II), are isomorphous as well as isostructural, and in each the thio­phene substituent is disordered over two sets of atomic sites having occupancies 0.844 (3) and 0.156 (3) in (I), and 0.883 (2) and 0.117 (2) in (II). In each structure, the mol­ecules are linked into sheets by a combination of C—H⋯N and C—H⋯O hydrogen bonds. Comparisons are made with some related compounds