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Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2).

ABSTRACT: The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180?K. In the crystals of both compounds, the base molecules are in the lactam form and no acid–base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O—H?O and N—H?O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N—H?O hydrogen bonds, and the base dimers are further linked through another N—H?O hydrogen bond into a layer structure parallel to (01). The acid molecule and the base molecule are linked via an O—H?O hydrogen bond.

SUBMITTER: Gotoh K

PROVIDER: S-EPMC6281111 | biostudies-other | 2018 Dec

REPOSITORIES: biostudies-other

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Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine.

Project description:The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-di-chloro-3,6-dihy-droxy-1,4-benzo-quinone) with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine, namely, bis-(2-pyridone) chloranilic acid, 2C5H5NO·C6H2Cl2O4, (I), bis-(3-hy-droxy-pyridinium) chloranilate, 2C5H6NO+·C6Cl2O42-, (II), and bis-(4-hy-droxy-pyridinium) chloranilate, 2C5H6NO+·C6Cl2O42-, (III), have been determined at 120?K. In the crystal of (I), the base mol-ecule is in the lactam form and no acid-base inter-action involving H-atom transfer is observed. The acid mol-ecule lies on an inversion centre and the asymmetric unit consists of one half-mol-ecule of chloranilic acid and one 2-pyridone mol-ecule, which are linked via a short O-H?O hydrogen bond. 2-Pyridone mol-ecules form a head-to-head dimer via a pair of N-H?O hydrogen bonds, resulting in a tape structure along [201]. In the crystals of (II) and (III), acid-base inter-actions involving H-atom transfer are observed and the divalent cations lie on an inversion centre. The asymmetric unit of (II) consists of one half of a chloranilate anion and one 3-hy-droxy-pyridinium cation, while that of (III) comprises two independent halves of anions and two 4-hy-droxy-pyridinium cations. The primary inter-molecular inter-action in (II) is a bifurcated O-H?(O,O) hydrogen bond between the cation and the anion. The hydrogen-bonded units are further linked via N-H?O hydrogen bonds, forming a layer parallel to the bc plane. In (III), one anion is surrounded by four cations via O-H?O and C-H?O hydrogen bonds, while the other is surrounded by four cations via N-H?O and C-H?Cl hydrogen bonds. These inter-actions link the cations and the anions into a layer parallel to (301).

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