Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine

Gallagher, John F.; Brady, Fiona; Murphy, Catríona

doi:10.1107/s010876819901561x

Cited by 3 publications

(4 citation statements)

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“…The thienyl system is oriented at an angle of 20.94 (12) to the C 5 H 4 ring and 5.95 (15) to the O1/O2/C1/C2 carboxylic acid plane. The angles involving the COOH group are normal (Gallagher et al, 2000). However, the angles centred at C2 are noteworthy.…”

Section: Crystal Structure Communicationsmentioning

confidence: 93%

Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Gallagher¹,

Hudson²,

Manning³

2001

Acta Crystallogr C

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The title compound, [Fe(C 5 H 5 )(C 10 H 7 O 2 S)], an important precursor en route to organometallic donor±%±acceptor systems, forms dimers in the solid state through cyclic intermolecular carboxylic acid OÐHÁ Á ÁO hydrogen bonds, graph set R CommentThe design of new redox-active compounds for application in materials science has engaged chemists in recent years. Ferrocene derivatives which are ef®cient redox systems have been studied extensively as charge-transfer complexes, in molecular recognition science, in peptide chemistry and as non-linear optical materials (Moore et al., 1993;Chesney et al., 1998;Glidewell et al., 1997;Kraatz et al., 1999;Hudson et al., 2001). An understanding of the interactions present in the crystal structure of a new material can provide valuable information on the hydrogen-bonding modes, thus facilitating an understanding of solid-state effects and the subsequent design and improvement of currently available systems. The structure of 2-(ferrocenyl)thiophene-3-carboxylic acid, (V), an important precursor en route to organometallic donor±%± acceptor systems, is reported herein.The synthesis of compound (V) is detailed in the Experimental section and the molecular structure is depicted, with the atomic numbering scheme, in Fig. 1; selected geometric dimensions are given in Table 1. Bond lengths are in accord with the anticipated values (Orpen et al., 1994). The unsubstituted cyclopentadienyl (Cp) ring is disordered over two sites, with occupancies of 0.691 (18) and 0.309 (18) for the major and minor orientations, respectively. Rotational disorder is often observed in the unsubstituted C 5 H 5 ring of ferrocene derivatives, e.g. 1-ferrocenyl-1-phenylethanol (Ferguson et al., 1993). The Fe1ÐC bond lengths for the substituted Cp ring of (V) are in the range 2.028 (2)± 2.050 (2) A Ê , which is similar to that observed for the major orientation of the unsubstituted Cp ring [2.039 (4)± 2.051 (7) A Ê ]. The Fe1Á Á ÁCg1 and Fe1Á Á ÁCg2 distances are 1.6435 (10) and 1.656 (3) A Ê , respectively, and the Acta Crystallographica Section C Crystal Structure CommunicationsISSN 0108-2701 Figure 1 An ORTEX (McArdle, 1995) view of (V) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The minor Cp-ring disorder form has been omitted for clarity.

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Section: Crystal Structure Communicationsmentioning

confidence: 93%

Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Gallagher¹,

Hudson²,

Manning³

2001

Acta Crystallogr C

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“…Structure-based drug design strategies to identify interactions between a potential inhibitor and target receptor require accurate inhibitor structures. We are currently studying structure±activity relationships and molecular-recognition processes in biologically important molecules such as the title compound N-3,5-dinitrobenzoyl-lleucine, (I), for applications in drug design (Gallagher & Murphy, 1999;Gallagher et al, , 2000.…”

Section: Commentmentioning

confidence: 99%

Intermolecular hydrogen bonding of the two independent molecules of N-3,5-dinitrobenzoyl-L-leucine

Gallagher¹,

Kenny²,

O'Donohoe³

2000

Acta Crystallogr C

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“…29 (14) in the chiral, (V), and racemic forms, (VI), of related threonine structures (Gallagher et al, 2000).…”

Section: Acta Cryst (2000) C56 619±622mentioning

confidence: 99%

“…Amino acids constitute a fundamental building block in biological compounds and valine derivatives have been utilized in the formation of chiral host lattices (Weigand et al, 1998). The title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, (I), and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, (II), derived from l-norvaline and l-valine, respectively, form part of a systematic study of hydrogen-bonding interactions in a series of amino acid derivatives (Brady et al, 1998;Dalton et al, 1999;Gallagher & Murphy, 1999;Gallagher et al, 2000).Compound (I) crystallizes in space group P2 1 2 1 2 1 with one molecule in the asymmetric unit and a view of (I) with the atomic numbering scheme is given in Fig. 1, with selected dimensions in Table 1.…”

mentioning

confidence: 99%

O—H...O, C—H...O and C—H...π_areneintermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid

Gallagher

Brady

2000

Acta Crystallogr C

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In the ®rst of the title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, C 13 H 15 NO 3 , prepared from l-norvaline, a hydrogen-bonded network is formed in the solid state through OÐHÁ Á ÁO C, CÐHÁ Á ÁO C and CÐ HÁ Á Á% arene intermolecular interactions, with shortest OÁ Á ÁO, CÁ Á ÁO and CÁ Á Ácentroid distances of 2.582 (13), 3.231 (11) and 3.466 (3) A Ê , respectively. In the l-valine derivative, (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, C 13 H 15 NO 3 , OÐHÁ Á ÁO C and C arene ÐHÁ Á ÁO C intermolecular interactions generate a cyclic R 2 2 (9) motif through cooperativity, with shortest OÁ Á ÁO and CÁ Á ÁO distances of 2.634 (3) and 3.529 (5) A Ê , respectively. Methylene CÐ HÁ Á ÁO C indole interactions complete the hydrogen bonding, with CÁ Á ÁO distances ranging from 3.283 (4) to 3.477 (4) A Ê . CommentPhthalimidines (isoindolin-1-ones) often display biological activity as potential anti-in¯ammatory agents and antipsychotics (Mukherjee et al., 2000), and most of the structurally determined systems are either N-substituted or have a hydroxy substituent at the 3-position (McNab et al., 1997;Kundu et al., 1999). Amino acids constitute a fundamental building block in biological compounds and valine derivatives have been utilized in the formation of chiral host lattices (Weigand et al., 1998). The title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, (I), and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, (II), derived from l-norvaline and l-valine, respectively, form part of a systematic study of hydrogen-bonding interactions in a series of amino acid derivatives (Brady et al., 1998;Dalton et al., 1999;Gallagher & Murphy, 1999;Gallagher et al., 2000).Compound (I) crystallizes in space group P2 1 2 1 2 1 with one molecule in the asymmetric unit and a view of (I) with the atomic numbering scheme is given in Fig. 1, with selected dimensions in Table 1. The bond lengths and angles in the heterocyclic ring are similar to those reported previously (McNab et al., 1997;Brady et al., 1998;Gallagher & Murphy, 1999) and are in agreement with expected values (Orpen et al., 1994). The carboxylic acid group exhibits rotational disorder, with site occupancies of 0.55 (4) and 0.45 (4) for the major and minor orientations, respectively. The angle between the CO 2 planes is 31 (3) and the major CO 2 orientation is at an angle of 67 (2) to the C 4 N ring plane [87.1 (16) for the minor site]. The angle between the ®ve-and six-membered rings of the isoindole system is 1.37 (17) and the maximum deviation from planarity for an atom in either ring plane is 0.0084 (16) A Ê for C9 (C 6 ring), with the carbonyl O3 atom 0.026 (3) A Ê from the C 4 N ring plane. The n-propyl chain adopts two conformations, with site occupancies of 0.519 (11) and 0.481 (11); details are given in the Experimental section.The hydrogen bonding in (I) is dominated by OÐ HÁ Á ÁO C, CÐHÁ Á ÁO C and C arene ÐHÁ Á Á% arene intermolecular interactions (Table 2 and Fig. 2). Convention...

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Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine

Cited by 3 publications

References 10 publications

Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Intermolecular hydrogen bonding of the two independent molecules of N-3,5-dinitrobenzoyl-L-leucine

O—H...O, C—H...O and C—H...π_areneintermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid

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Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine

Cited by 3 publications

References 10 publications

Intermolecular O—H...O and C—H...π(C5H5), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Intermolecular O—H...O and C—H...π(C5H5), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Intermolecular hydrogen bonding of the two independent molecules of N-3,5-dinitrobenzoyl-L-leucine

O—H...O, C—H...O and C—H...πareneintermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid

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Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

Intermolecular O—H...O and C—H...π(C₅H₅), and intramolecular C—H...O interactions in 2-(ferrocenyl)thiophene-3-carboxylic acid

O—H...O, C—H...O and C—H...π_areneintermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid