O—H...O, C—H...O and C—H...πareneIntermolecular Interactions in (2R/2S)-2-(1-oxo-1,3-dihydroisoindol-2-yl)-3-phenylpropanoic Acid

Brady, Fiona; Gallagher, John F.; Kenny, Peter T.M.

doi:10.1107/s0108270198005678

Cited by 4 publications

(6 citation statements)

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“…1 and selected dimensions are in Table 1. The bond lengths and angles in the heterocyclic ring are similar to those reported previously (Brady et al, 1998) and in agreement with expected values (Orpen et al, 1994). The angle between the five-and six-membered rings of the isoindole system is 0.95 (13) ° and the maximum deviation from oplanarity for an atom in either ring plane is 0.0179 (12) A for C3, with the carbonyl 03 atom 0.096 (3),~ from the CaN ring plane.…”

Section: Commentsupporting

confidence: 76%

“…This ring is almost perpendicular to both the carboxylic acid CCO2 plane, 83.12 (8) ° and the 3-phenyl ring plane, 87.15 (7) °. Stacking arises involving the 7r-Tr systems of inversion symmetry-related isoindo[e groups (RS pairs), with an interplanar distance of 3.43 A [3.35 A in the DL-phenylalanine derivative (2R/2S)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoic acid, (II), which has a similar molecular geometry (Brady et al, 1998)]. Examination of (I) with PLATON (Spek, 1998) revealed voids in the crystal lattice of volume 7 ,~3 (x4) which are too small to accommodate a solvent molecule.…”

Section: Commentmentioning

confidence: 99%

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C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

Gallagher¹,

Murphy²

1999

Acta Crystallogr C

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Section: Commentsupporting

confidence: 76%

Section: Commentmentioning

confidence: 99%

C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

Gallagher¹,

Murphy²

1999

Acta Crystallogr C

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“…10(a). Weak C6A-H6CÁ Á Á(Cg5) and C14A-H14BÁ Á Á(Cg2) viii [symmetry code: (viii) Àx, Ày + 1, Àz] interactions (Cg5 is the centroid of the C18A/C19A/C24A/C25A/C26A/C31A ring and Cg2 that of the C8A-C13A ring), with distances of 2.93 (Brady et al, 1998) and 2.75 Å (Selvanayagam et al, 2015), are observed ( Fig. 10b).…”

Section: Tablementioning

confidence: 99%

“…14a). In addition, a C14-H14Á Á ÁCg1 interaction is present [2.72 Å and 177 ;Brady et al, 1998; symmetry code: Àx + 1, Ày + 1, Àz + 1] (Fig. 14b).…”

Section: Figure 13mentioning

confidence: 99%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Darious

Muthiah

Perdih

2018

Acta Crystallogr C Struct Chem

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Nine salts of the antifolate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate monohydrate (TMPDCTPC, 1:1), CHNO·CHClOS, (I), trimethoprimium 3-bromothiophene-2-carboxylate monohydrate, (TMPBTPC, 1:1:1), CHNO·CHBrOS·HO, (II), trimethoprimium 3-chlorothiophene-2-carboxylate monohydrate (TMPCTPC, 1:1:1), CHNO·CHClOS·HO, (III), trimethoprimium 5-methylthiophene-2-carboxylate monohydrate (TMPMTPC, 1:1:1), CHNO·CHOS·HO, (IV), trimethoprimium anthracene-9-carboxylate sesquihydrate (TMPAC, 2:2:3), CHNO·CHO·1.5HO, (V), pyrimethaminium [or 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate (PMNDCTPC, 1:1), CHClN·CHClOS, (VI), pyrimethaminium 5-bromothiophene-2-carboxylate (PMNBTPC, 1:1), CHClN·CHBrOS, (VII), pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), CHClN·CHO·CHOH·HO, (VIII), and bis(pyrimethaminium) naphthalene-1,5-disulfonate (PMNNSA, 2:1), 2CHClN·CHOS, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)-(III) and (VI)-(IX), the 2-aminopyrimidinium cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds, generating the robust R(8) supramolecular heterosynthon. In salt (IV), instead of forming the R(8) heterosynthon, the carboxylate group bridges two pyrimidinium cations via N-H...O hydrogen bonds. In salt (V), one of the carboxylate O atoms bridges the N1-H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R(6) ring instead of the R(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxylate O atoms in forming an R(8) ring motif. In salts (II)-(IX), the pyrimidinium cation forms base pairs via a pair of N-H...N hydrogen bonds, generating a ring motif [R(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)-(IV) and (VI)-(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π-π stacking interactions [in (I), (V) and (VII)-(IX)], C-H...π interactions [in (IV)-(V) and (VII)-(IX)], C-Br...π interactions [in (II)] and C-Cl...π interactions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond interactions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

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“…The title compound, (I), synthesized from dl-tyrosine and orthophthalaldehyde (Allin et al, 1996), forms part of a study of phthalimidines incorporating an aromatic residue (Brady et al, 1998;Brady & Gallagher, 2000;Gallagher & Murphy, 1999).…”

Section: Commentmentioning

confidence: 99%

(2RS)-3-(4-Hydroxyphenyl)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)propanoic acid monohydrate

Gallagher

Brady

2007

Acta Cryst E

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water molecule O1W forming an R 3 3 (10) ring (Fig. 1, Table 2). The other water O2W is positioned between O1W and the isoindole O3A, providing a complex arrangement of hydrogen-bonded rings with motifs R 3 3 (10)R 3 3 (11)[R 4 4 (15)] (Bernstein et al., 1995). Dimers link through (aryl A/B)O4-H4Á Á ÁO3=C3 B/A hydrogen bonds, forming a one-dimensional chain of rings connected as graph set R 2 2 (22) (Fig. 2), that associate further through centres of symmetry forming a column along [101], comprising two chains of rings linked and oriented in opposite directions. Such R 2 2 (22) rings are also a key feature in the crystal structure of (II). In (I), the column can also be described as assembling from dimers into tetramers (Fig. 3) and association into columns through (aryl)O-HÁ Á ÁO C interactions (Fig. 4). Columns interlock viaarene stacking interactions about inversion centres, forming ruffled sheets [isoindole C 6 ring interplanar distance of 3.37 Å , substantially offset with Cg1Á Á ÁCg1 vii = 3.769 (2) Å , where Cg1 is the C4B-C9B ring centroid and symmetry code: (vii) Àx, Ày, Àz], in tandem with C-HÁ Á Á(arene) interactions (Fig. 5, Table 2) and C-HÁ Á ÁO interactions. The cumulative effect yields a complex hydrogenbond pattern as a three-dimensional network (Fig. 6). The hydrogen bonding network involving O1W and O2W is uncommon as O2W forms only one strong hydrogen bond (Figs. 1-3). Water O1W is an acceptor for the acidic O1B-H1B group [OÁ Á ÁO = 2.610 (3) Å , Table 2]. The O1W-H1 donor forms a bifurcated interaction with O3B iii /O2A [OÁ Á ÁO 2.982 (3)/3.149 (3) Å : symmetry operation iii, Table 2] and organic papers o2208 Gallagher and Brady C 17 H 15 NO 4 ÁH 2 O

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O—H...O, C—H...O and C—H...π_areneIntermolecular Interactions in (2R/2S)-2-(1-oxo-1,3-dihydroisoindol-2-yl)-3-phenylpropanoic Acid

Abstract: The title compound, CI7HIsNO3, forms a hydrogenbonded network in the solid state consisting of O-H-.

Cited by 4 publications

References 2 publications

C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

(2RS)-3-(4-Hydroxyphenyl)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)propanoic acid monohydrate

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O—H...O, C—H...O and C—H...πareneIntermolecular Interactions in (2R/2S)-2-(1-oxo-1,3-dihydroisoindol-2-yl)-3-phenylpropanoic Acid

Abstract: The title compound, CI7HIsNO3, forms a hydrogenbonded network in the solid state consisting of O-H-.

Cited by 4 publications

References 2 publications

C—H...πarene, Csp3—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

C—H...πarene, Csp3—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

(2RS)-3-(4-Hydroxyphenyl)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)propanoic acid monohydrate

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O—H...O, C—H...O and C—H...π_areneIntermolecular Interactions in (2R/2S)-2-(1-oxo-1,3-dihydroisoindol-2-yl)-3-phenylpropanoic Acid

C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative

C—H...π_arene, Csp³—H...O=C and O—H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: ameta-tyrosine derivative