2-(5-Benzyloxy-2,4-dichlorophenyl)perhydroisoindole-1,3-dione monohydrate

Wang, Neng-Xue; Luo, Yongping; Chen, Qiong; Yang, Guang‐Fu

doi:10.1107/s1600536805017770

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“…The structures reported here expand the structural database for compounds of this series, formed in the facile reaction of cis-CHDC anhydride with substituted anilines, among which there is a much larger incidence of cyclic imides compared to amide carboxylic acids [currently 8:3, among known examples, which, apart from our previously reported structures, include the imide from the reaction with 5-benzyloxy-2,4-dichloroaniline (Wang et al, 2005) and those from the reactions with 4-bromoaniline and 5-aminosalicylic acid (Smith & Wermuth, 2012b)]. However, there are no apparent structural features which might allow a definitive prediction of the preferred reaction product.…”

Section: Figurementioning

confidence: 87%

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

Smith

Wermuth

2012

Acta Crystallogr C

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The structures of the open-chain amide carboxylic acid rac-cis-2-[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic acid, C(15)H(19)NO(4), (I), and the cyclic imides rac-cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, C(15)H(17)NO(3), (II), chiral cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C(15)H(15)NO(4), (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid monohydrate, C(15)H(15)NO(4)·H(2)O, (IV), are reported. In the amide acid (I), the phenylcarbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) Å for the amide O atom] and the molecules form discrete centrosymmetric dimers through intermolecular cyclic carboxy-carboxy O-H···O hydrogen-bonding interactions [graph-set notation R(2)(2)(8)]. The cyclic imides (II)-(IV) are conformationally similar, with comparable benzene ring rotations about the imide N-C(ar) bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak intermolecular C-H···O(imide) hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong intermolecular carboxylic acid O-H···O hydrogen-bonding associations. With (III), these involve imide O-atom acceptors, giving one-dimensional zigzag chains [graph-set C(9)], while with the monohydrate (IV), the hydrogen bond involves the partially disordered water molecule which also bridges molecules through both imide and carboxy O-atom acceptors in a cyclic R(4)(4)(12) association, giving a two-dimensional sheet structure. The structures reported here expand the structural database for compounds of this series formed from the facile reaction of cis-cyclohexane-1,2-dicarboxylic anhydride with substituted anilines, in which there is a much larger incidence of cyclic imides compared to amide carboxylic acids.

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Section: Figurementioning

confidence: 87%

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

Smith

Wermuth

2012

Acta Crystallogr C

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2-(5-Benzyloxy-2,4-dichlorophenyl)perhydroisoindole-1,3-dione monohydrate

Abstract: The crystal structure of the title compound, C21H19Cl2NO3·H2O, shows that there are no intra‐ or intermolecular π—π stacking interactions. The structure is stabilized by O—H⋯O hydrogen bonds involving the carbonyl group and the solvent water molecule.

Cited by 1 publication

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Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

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2-(5-Benzyloxy-2,4-dichlorophenyl)perhydroisoindole-1,3-dione monohydrate

Abstract: The crystal structure of the title compound, C21H19Cl2NO3·H2O, shows that there are no intra‐ or inter­molecular π—π stacking inter­actions. The structure is stabilized by O—H⋯O hydrogen bonds involving the carbon­yl group and the solvent water mol­ecule.

Cited by 1 publication

References 1 publication

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction ofcis-cyclohexane-1,2-carboxylic anhydride witho- andp-anisidine andm- andp-aminobenzoic acids

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Abstract: The crystal structure of the title compound, C21H19Cl2NO3·H2O, shows that there are no intra‐ or intermolecular π—π stacking interactions. The structure is stabilized by O—H⋯O hydrogen bonds involving the carbonyl group and the solvent water molecule.