Reinvestigation of the crystal structure of<i>N</i>-(4-chlorobenzylidene)-2-hydroxyaniline: a three-dimensional structure containing O—H...N, O—H...O and C—H...π(arene) hydrogen bonds

Girisha, Marisiddaiah; Yathirajan, H. S.; Rathore, R. S.; Glidewell, Christopher

doi:10.1107/s205698901800244x

Cited by 3 publications

(3 citation statements)

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“…In (E)-N-(4-nitrobenzylidene)-2,3-dimethylaniline, (II) , and (E)-N-(4-nitrobenzylidene)-3,4-dimethoxyaniline, (III) (Akkurt et al, 2008), the dihedral angles between the two aryl rings are 24.52 (5) and 29.52 (8) , respectively. By contrast, in (E)-N-(4-nitrobenzylidene)-2-hydroxyaniline), (IV) (Madhuprasad et al, 2014), and (E)-N-(4-chlorobenzylidene)-2-hydroxyaniline, (V) (Girisha et al, 2018), the dihedral angles between the rings are 0.52 [the atomic coordinates retrieved from the CSD (Groom et al, 2016) carry no s.u.s] and 3.31 (9) respectively, reflecting the influence of the intramolecular O-HÁ Á ÁN hydrogen bonds in these two compounds.…”

Section: Structural Commentarymentioning

confidence: 93%

“…Schiff bases exhibit a very wide range of biological activities (da Silva et al, 2011) and are also of interest because of their photochromic and thermochromic properties (Hadjoudis & Mavridis, 2004;Minkin et al, 2011). In view of the general importance of Schiff bases, and in a continuation of our own structural study of compounds of this type (Girisha et al, 2017(Girisha et al, , 2018 we report here the molecular and supramoleuclar structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline (I) ( Fig. 1), where the ethyl group turns out to be disordered over two sets of atomic sites and where the molecules are linked into a three-dimensional supramolecular array.…”

Section: Chemical Contextmentioning

confidence: 99%

“…The structure of compound (III) (Akkurt et al, 2008) contains three short C-HÁ Á ÁO contacts, but two of these involve an H atom in a methyl group, while for the third the C-HÁ Á ÁO angle is only 131 , so that none of these contacts is likely to be structurally significant (Wood et al, 2009). The molecules of compound (IV) (Madhuprasad et al, 2014) are linked into centrosymmetric dimers by inversionrelated O-HÁ Á ÁO hydrogen bonds, while those of compound (V) are linked into a three-dimensional framework structure by a combination of C-HÁ Á ÁO and C-HÁ Á Á(arene) hydrogen bonds and an aromaticstacking interaction (Girisha et al, 2018).…”

Section: Database Surveymentioning

confidence: 99%

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The crystal structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline: three-dimensional supramolecular assembly mediated by C—H...O hydrogen bonds and nitro...π(arene) interactions

et al. 2018

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Section: Structural Commentarymentioning

confidence: 93%

Section: Chemical Contextmentioning

confidence: 99%

Section: Database Surveymentioning

confidence: 99%

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The crystal structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline: three-dimensional supramolecular assembly mediated by C—H...O hydrogen bonds and nitro...π(arene) interactions

et al. 2018

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Eight Schiff bases derived from various salicylaldehydes: phenol–imine and keto–amine forms, conformational disorder, and supramolecular assembly in one and two dimensions

Girisha

Sagar

Yathirajan

et al. 2018

Acta Crystallogr C Struct Chem

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Structures are reported for eight Schiff bases derived from various salicylaldehydes: five are newly synthesized and re-investigations are reported for three previously reported structures, leading, in each case, to some revision of previous conclusions. In (E)-N-(3,4-dimethylisoxazol-5-yl)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide, C18H17N3O4S, (I), and (E)-4-[(5-bromo-2-hydroxy-3-methoxybenzylidene)amino]-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide. C19H18BrN3O5S, (II), the isoxazole rings adopt different orientations relative to the rest of the molecules, despite the additional substituents in (II) being in the aryl ring remote from the isoxazole unit. The molecules of both (E)-4-bromo-2-[(2-hydroxyphenylimino)methyl]-6-methoxyphenol, C14H12BrNO3, (III), and (E)-4-bromo-2-methoxy-6-[(2-methoxyphenylimino)methyl]phenol, C15H14BrNO3, (IV), are both effectively planar; while (III) adopts the phenol–imine constitution, (IV) adopts the keto–amine constitution. (E)-2-Methoxy-6-[(2-methoxyphenylimino)methyl]phenol, C15H15NO3, (V), which was determined previously using powder X-ray data assuming the phenol–imine constitution, has now been refined from single-crystal X-ray data, confirming the phenol–imine constitution. In (E)-3-benzoyl-2-[(5-fluoro-2-hydroxybenzylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene, C22H18FNO2S, (VI), the fused carbocyclic ring exhibits conformational disorder; both disorder components, having populations of 0.705 (4) and 0.295 (4), adopt half-chair conformations. The isostructural (E)-3-benzoyl-2-[(2-hydroxybenzylidene)amino)]-4,5,6,7-tetrahydrobenzo[b]thiophene, C22H19NO2S, (VII), which was originally reported as having a fully ordered structure [Kaur et al. (2014). Acta Cryst. E70, o476–o477], has been rerefined using the original data set and found to exhibit the same type of disorder as found in (VI), with disordered populations having occupancies of 0.851 (3) and 0.149 (3). The triclinic polymorph of (E)-[(2-hydroxyphenylimino)methyl]phenol, C13H11NO2, (VIII), which crystallizes with Z′ = 2 in the space group P-1, has been described variously as occurring as the keto–amine tautomer [Maciejewska et al. (1999). J. Phys. Org. Chem. 12, 875–880] and as the phenol–imine tautomer [Tunç et al. (2009). J. Chem. Crystallogr. 39, 672–676]. Rerefinement of this structure using one of the original data sets shows that both of the independent molecules exist in the keto–amine form. In the structures of compounds (I), (VI), (VII) and (VIII), hydrogen bonds generate simple chains, while a chain of rings is formed in (V). Sheets are formed by hydrogen bonds in both (II) and (III), while in (IV), the sheet structure is built from aromatic π–π stacking interactions.

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Crystal structure and Hirshfeld surface analysis of (E)-N′-benzylidene-4-chlorobenzenesulfonohydrazide and of its (E)-4-chloro-N′-(ortho- and para-methylbenzylidene)benzenesulfonohydrazide derivatives

2018

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The crystal structures of (E)-N′-(benzylidene)-4-chlorobenzenesulfonohydrazide (I) and its ortho- and para-methyl-substituted benzylidene derivatives, (E)-N′-(2-methylbenzylidene)-4-chloro-benzenesulfonohydrazide (II) and (E)-N′-(4-methylbenzylidene)-4-chlorobenzenesulfonohydrazide (III), have been studied to investigate the effect of substitution on the structural and supramolecular features of these compounds.

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Reinvestigation of the crystal structure ofN-(4-chlorobenzylidene)-2-hydroxyaniline: a three-dimensional structure containing O—H...N, O—H...O and C—H...π(arene) hydrogen bonds

Cited by 3 publications

References 13 publications

The crystal structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline: three-dimensional supramolecular assembly mediated by C—H...O hydrogen bonds and nitro...π(arene) interactions

The crystal structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline: three-dimensional supramolecular assembly mediated by C—H...O hydrogen bonds and nitro...π(arene) interactions

Eight Schiff bases derived from various salicylaldehydes: phenol–imine and keto–amine forms, conformational disorder, and supramolecular assembly in one and two dimensions

Crystal structure and Hirshfeld surface analysis of (E)-N′-benzylidene-4-chlorobenzenesulfonohydrazide and of its (E)-4-chloro-N′-(ortho- and para-methylbenzylidene)benzenesulfonohydrazide derivatives

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