Co-crystallization of 3,5-dinitrobenzoic acid with trihexyphenidyl [or 1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol], gives a 1:1 salt (I) but chlorprothixene [or (Z)-3-(2-chloro-9H-thioxanthen-9-yl)-N,N-dimethylpropan-1-amine], gives a 1:2 acid salt (II) containing a very short O—H⋯O hydrogen bond. Multiple hydrogen bonds link the ions in (I) into a complex chain of rings and those in (II) link the ions into a sheet.
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, C 32 H 40 NO 2 + ÁC 7 H 3 N 2 O 6 À . 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 Ph 2 CH-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-HÁ Á ÁO hydrogen bond and this, in combination with two C-HÁ Á ÁO hydrogen bonds, links the ions into complex sheets. Chemical contextEbastine, or 4-(benzhydryloxy)-1-[4-(4-tert-butylphenyl)-4-oxobutyl]piperidine, is a non-sedating second generation H 1 receptor antagonist, which is effective in the treatment of both allergic rhinitis, whether seasonal or perennial, and chronic idiopathic urticaria (Wiseman & Faulds, 1996;Van Cauwenberge et al., 2004). The structure of ebastine has been the subject of two recent reports (Cheng et al., 2005: Sharma et al., 2015. Herein, we report the molecular and supramolecular structure of the 1:1 salt ebastinium 3,5-dinitrobenzoate (I), formed in the reaction between ebastine and 3,5-dinitrobenzoic acid. Structural commentaryThe title compound (I), consists of an N-protonated ebastinium cation and a 3,5-dinitrobenzoate anion (Fig. 1), which ISSN 2056-9890 are linked within the selected asymmetric unit a by a fairly short and nearly linear N-HÁ Á ÁO hydrogen bond (Fig. 1, Table 1). The disubstituted aryl ring in the cation is disordered over two sets of atomic sites having occupancies 0.706 (4) for the major ring orientation, labelled C161-C166, and 0.294 (4) for the minor orientation, labeled C171-C176: the dihedral angle between these two ring planes is 41.2 (5) (Fig. 1). The piperidine ring adopts an almost perfect chair conformation, with a ring-puckering angle, calculated for the atom sequence (N1,C2,C3,C4,C5,C6) of = 0.0 (3), identical within experimental uncertainty to the idealized value for a perfect chair form of = 0.0 (Boeyens, 1978). However, although the non-H substituent at atom N1 in the ring occupies an equatorial site, as expected, the bulky Ph 2 CHO substituent at atom C4 unexpectedly occupies an axial site. This observation is the more surprising since in ebastine itself, both non-H substituents on the piperidine ring occupy equatorial sites (Cheng et al., 2005: Sharma et al., 2015. The 3,5-dinitrobenzoate anion in compound (I) is nearly planar: the dihedral angles between the aryl ring and the substituents at atoms C21, C23 and C25 are 1.4 (2), 4.2 (2) and 10.7 (2) , respectively: only the O atoms of the 5-nitro group are significantly displaced from the mean plane of the anion as a whole, 0.219 (2) Å for atom O25 and 0.187 (2) Å for atom O26: the r.m.s. deviation from the mean plane for the entire anion is only 0.082 Å . Supramolecular featuresIn addition to the ...
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.
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—H...π(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.
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.
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