In the first of the title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, C₁₃H₁₅NO₃, prepared from L-norvaline, a hydrogen-bonded network is formed in the solid state through O-H...O=C, C-H...O=C and C-H...πarene intermolecular interactions, with shortest O...O, C...O and C...centroid distances of 2.582 (13), 3.231 (11) and 3.466 (3) Å, respectively. In the L-valine derivative, (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, C₁₃H₁₅NO₃, O-H...O=C and Carene-H...O=C intermolecular interactions generate a cyclic R²₂(9) motif through cooperativity, with shortest O...O and C...O distances of 2.634 (3) and 3.529 (5) Å, respectively. Methylene C-H...O=Cindole interactions complete the hydrogen bonding, with C...O distances ranging from 3.283 (4) to 3.477 (4) Å

Brady, Fiona

Gallagher, John F.

English

John F. Gallagher

Fiona Brady

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O—H...O, C—H...O and C—H...π
                    arene

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OÐH  O, CÐH  O and CÐH  parene intermolecular interactionsin (2S)-2-(1-oxo-1H-2,3-dihydro-isoindol-2-yl)pentanoic acid and(2S)-3-methyl-2-(1-oxo-1H-2,3-di-hydroisoindol-2-yl)butanoic acidJohn F. Gallagher* and Fiona BradySchool of Chemical Sciences, Dublin City University, Dublin 9, IrelandCorrespondence e-mail: gallagherjfg@dcu.ieReceived 1 February 2000Accepted 7 March 2000In the ®rst of the title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, C13H15NO3, preparedfrom l-norvaline, a hydrogen-bonded network is formed inthe solid state through OÐH  O C, CÐH  O C and CÐH  arene intermolecular interactions, with shortest O  O,C  O and C  centroid distances of 2.582 (13), 3.231 (11) and3.466 (3) AÊ , respectively. In the l-valine derivative, (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid,C13H15NO3, OÐH  O C and CareneÐH  O C intermo-lecular interactions generate a cyclic R22(9) motif throughcooperativity, with shortest O  O and C  O distances of2.634 (3) and 3.529 (5) AÊ , respectively. Methylene CÐH  O Cindole interactions complete the hydrogen bonding,with C  O distances ranging from 3.283 (4) to 3.477 (4) AÊ .CommentPhthalimidines (isoindolin-1-ones) often display biologicalactivity as potential anti-in¯ammatory agents and anti-psychotics (Mukherjee et al., 2000), and most of the structu-rally determined systems are either N-substituted or have ahydroxy substituent at the 3-position (McNab et al., 1997;Kundu et al., 1999). Amino acids constitute a fundamentalbuilding block in biological compounds and valine derivativeshave 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, formpart of a systematic study of hydrogen-bonding interactions ina series of amino acid derivatives (Brady et al., 1998; Dalton etal., 1999; Gallagher & Murphy, 1999; Gallagher et al., 2000).Compound (I) crystallizes in space group P212121 with onemolecule in the asymmetric unit and a view of (I) with theatomic numbering scheme is given in Fig. 1, with selecteddimensions in Table 1. The bond lengths and angles in theheterocyclic 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 andminor orientations, respectively. The angle between the CO2planes is 31 (3) and the major CO2 orientation is at an angleof 67 (2) to the C4N ring plane [87.1 (16) for the minor site].The angle between the ®ve- and six-membered rings of theisoindole system is 1.37 (17) and the maximum deviationfrom planarity for an atom in either ring plane is 0.0084 (16) AÊfor C9 (C6 ring), with the carbonyl O3 atom 0.026 (3) AÊ fromthe C4N ring plane. The n-propyl chain adopts two confor-mations, 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 OÐH  O C, CÐH  O C and CareneÐH  arene inter-molecular interactions (Table 2 and Fig. 2). Conventional OÐH  O hydrogen bonding is not observed, either betweenpairs of carboxylic acid groups [graph set R22(8); Ferguson etal., 1995] or through interaction of the COOH group with aCÐH/C O pair from an isoindolin-1-one system [compound(III); graph set R22(9); Brady et al., 1998]. Carboxylic acid OÐH  O C hydrogen bonds are formed with the heterocyclicring C O group O1A/O1B  O3i = 2.582 (13)/2.640 (12) AÊ[symmetry code: (i) 1 ÿ x, y ÿ 12, 12 ÿ z], where B/A are themajor/minor carboxylate sites. A CareneÐH  O interactioninvolving the carboxylic acid C O moiety as C7ÐH7  O2Aii/O2Bii, with C  O = 3.231 (11)/3.49 (2) AÊ[symmetry code: (ii) 12 + x,12 ÿ y, 1 ÿ z], generates a chain ofCivareneÐH  O CÐOÐH  O Ciindole hydrogen bonds,Acta Cryst. (2000). C56, 619±622 # 2000 International Union of Crystallography  Printed in Great Britain ± all rights reserved 619organic compoundsActa Crystallographica Section CCrystal StructureCommunicationsISSN 0108-2701Figure 1A view of (I) with the atomic numbering scheme. Atom labels with thesuf®x A indicate one of the disordered conformations of the carboxylicacid and n-propyl groups. Displacement ellipsoids are drawn at the 30%probability level and H atoms are shown as small spheres of arbitraryradii.organic compounds620 Gallagher and Brady  Two isomers of C13H15NO3 Acta Cryst. (2000). C56, 619±622thus preventing the formation of a cyclic R22(9) system [Bradyet al., 1998; symmetry code: (iv) ÿ 12 x; 12ÿ y; 1ÿ z]. Furtherassociation of (I) through C8ÐH8  Cg1ii interactions[C8  Cg1ii = 3.466 (3) AÊ , where Cg1 is the C4±C9 ringcentroid] and C10methyleneÐH10A  O3iii interactions[C  Oiii = 3.335 (3) AÊ ], complete the hydrogen-bondingnetwork [symmetry code: (iii) 1 + x, y, z]. The orientation ofthe isoindole ring de®ned by C3ÐN1ÐC2ÐC1A isÿ95.3 (9), which is greater than the values of ÿ85.2 (2) in arelated 3-phenylpropanoic acid derivative, (III) (Brady et al.,1998), or ÿ86.6 (2) in a meta-tyrosine derivative, (IV)(Gallagher & Murphy, 1999), but smaller than the values ofÿ104.5 (3) and ÿ112.29 (14) in the chiral, (V), and racemicforms, (VI), of related threonine structures (Gallagher et al.,2000).Compound (II) crystallizes in space group P1, with twoindependent molecules, A and B, in the asymmetric unit,which differ slightly in conformation but retain the samecon®guration (S) at the chiral centre. A view of the asym-metric unit with the atomic numbering scheme is given inFig. 3 and selected dimensions are given in Table 3. Bondlengths and angles are in accord with anticipated values(Orpen et al., 1994). The r.m.s. deviation for the superpositionof the non-H atoms in both molecules is 0.39 AÊ (Spek, 1998).The angles between the ®ve- and six-membered rings of theisoindole system are 1.0 (2) (A) and 1.7 (2) (B), and themaximum deviation from planarity for an atom in eitherindole ring is 0.010 (3) AÊ for C7A, with the carbonyl O3 atom0.039 (5) (A) and 0.036 (5) AÊ (B) from the C4N ring plane. Theangles between the CCO2 group and the C4N ring planes are77.51 (11) and 79.28 (11) in molecules A and B, respectively.Torsion angle differences are evident from N1ÐC2ÐC11ÐC12 with values of ÿ43.6 (4) (A) and ÿ52.0 (3) (B) (Table 3).The orientations of the isoindole rings de®ned by C3ÐN1ÐC2ÐC1 are 57.3 (4) (A) and 60.7 (4) (B), and these values areopposite to those in structures (I)±(VI), presumably due tosteric hindrance of the isopropyl group in (II) compared withthe n-propyl group in (I).The hydrogen bonding in (II) is dominated by OÐH  O C, CÐH  O C and Csp3ÐH  O intermolecularinteractions (Table 4 and Fig. 4). Hydrogen-bonded rings withgraph set R22(9) are formed from the combination of acidO1A/BÐH1  O3B/A interactions with the heterocyclic ringC O group [2.642 (3) and 2.634 (3) AÊ , respectively] andarene C5B/AÐH5  O2A/B contacts with the carboxylic acidC O group [3.529 (5) and 3.714 (5) AÊ , respectively]. TheR22(9) motif is present in a related 3-phenylpropanoic acidsystem, (III) (Brady et al., 1998). This cooperativity generatesa hydrogen-bonded zigzag chain in the direction of the a and baxes. The hydrogen-bonded network is completed by C10ÐH10  O3 interactions in which all four methylene H atoms,H10A and H10B in A, and H10C and H10D in B, participate.The C5ÐH5  O2 distances are longer in (II) than those in(III), although the O  O distances are similar. This C  Odifference may be due to the weak intramolecular C13ÐH13  O2 contacts present in both molecules of (II).The hydrogen bonding in (I) and (II) is similar in terms ofhydrogen-bond numbers and associated distances per mol-ecule, with one OÐH  O, two CÐH  O and a CÐH  arene interaction in (I), comparable with the OÐH  Oand three CÐH  O interactions per molecule in (II). Theunit-cell volumes of 1265.3 AÊ 3 in (I) and 584.6 AÊ 3 in (II) showa difference of 24 AÊ 3 per molecule [316 AÊ 3 in (I) and 292 AÊ 3 in(II)], which can be accounted for by the carboxylic acid andn-propyl-group disorder in (I). The rotational disorder of thecarboxylic acid group is assisted by the looser interactionsinvolving the carboxylate O2 atom in (I). Examination of (II)and the major conformation of (I) with PLATON (Spek,Figure 2A view of the intermolecular interactions of (I) with the majorconformation only; symmetry codes are as given in Table 2.Figure 3A view of the two independent molecules in the asymmetric unit of (II)with the atomic numbering scheme. Displacement ellipsoids are drawn atthe 30% probability level and H atoms are shown as small spheres ofarbitrary radii.1998) showed that there were no solvent-accessible voids ineither crystal lattice. The hydrogen bonding in (II) can becompared with that of the two independent molecules whichdiffer slightly in conformation in N,N0-dicyclohexyl-N-(3-pyridylcarbonyl)urea (Gallagher et al., 1999). The overallcrystal structure of (II) may be facilitated through hydrogen-bonded oligomeric units crystallizing from solution to producethe primary [A  B  ]n hydrogen-bonded chain.ExperimentalThe title compounds, (I) and (II), were prepared by the overnightreaction of o-phthalaldehyde with l-norvaline and l-valine, respec-tively, in re¯uxing CH3CN under N2 (Allin et al., 1996). Filtration ofthe hot solution and subsequent slow cooling of the ®ltrate allowedthe isolation of large colourless crystals from CH3CN. Spectroscopicanalysis for (I), m.p. 467±468 K (uncorrected): IR (C O, cmÿ1): 1730,1649 (KBr); 1H NMR (400 MHz, , d6-DMSO): 0.89 (t, 3H, CH3), 1.29(br m, 2H, CH2), 1.90 (br m, 2H, CH2), 4.49 (q, 2H, CH2), 4.77 (m, 1H,CH), 7.48±7.51, 7.69±7.72 (m, 4H, C6H4). Spectroscopic analysis for(II), m.p. 436±438 K (uncorrected): IR (C O cmÿ1): 1734, 1647, 1634(KBr); 1H NMR (400 MHz, , d6-DMSO): 0.84 (d, 3H, CH3), 1.02 (d,3H, CH3), 2.29 (br m, 1H, CH), 4.53 (m, 2H, CH2), 4.63 (m, 1H, CH),7.30±7.37, 7.69±7.72 (m, 4H, C6H4).Compound (I)Crystal dataC13H15NO3Mr = 233.26Orthorhombic, P212121a = 5.9384 (4) AÊb = 12.3808 (9) AÊc = 17.2097 (14) AÊV = 1265.29 (16) AÊ 3Z = 4Dx = 1.224 Mg mÿ3Mo K radiationCell parameters from 25re¯ections = 9.49±19.63 = 0.087 mmÿ1T = 294 (1) KBlock, colourless0.48  0.20  0.18 mmData collectionEnraf±Nonius CAD-4 diffract-ometer!/2 scans4433 measured re¯ections1313 independent re¯ections1001 re¯ections with I > 2(I)Rint = 0.011max = 25h = 0! 7k = ÿ14! 14l = ÿ20! 203 standard re¯ectionsfrequency: 120 minintensity decay: <1%Re®nementRe®nement on F 2R[F 2 > 2(F 2)] = 0.029wR(F 2) = 0.076S = 1.0201313 re¯ections202 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.0451P)2+ 0.0395P]where P = (Fo2 + 2Fc2)/3(/)max < 0.001max = 0.09 e AÊÿ3min = ÿ0.10 e AÊ ÿ3Extinction correction: SHELXL97(Sheldrick, 1997)Extinction coef®cient: 0.047 (5)Compound (II)Crystal dataC13H15NO3Mr = 233.26Triclinic, P1a = 5.8767 (6) AÊb = 9.9036 (13) AÊc = 10.4818 (15) AÊ = 103.332 (13) = 99.759 (11) = 89.792 (11)V = 584.62 (13) AÊ 3Z = 2Dx = 1.325 Mg mÿ3Mo K radiationCell parameters from 25re¯ections = 9.48±19.91 = 0.094 mmÿ1T = 294 (1) KPlate, colourless0.45  0.35  0.14 mmActa Cryst. (2000). C56, 619±622 Gallagher and Brady  Two isomers of C13H15NO3 621organic compoundsFigure 4A view of the intermolecular interactions in (II); symmetry codes are asgiven in Table 4.Table 1Selected geometric parameters (AÊ , ) for (I).O3ÐC3 1.243 (3)N1ÐC3 1.343 (3)N1ÐC2 1.444 (3)N1ÐC10 1.461 (3)C2ÐC11 1.516 (4)C3ÐC4 1.467 (3)C9ÐC10 1.490 (3)C2ÐN1ÐC3 122.8 (2)C2ÐN1ÐC10 124.3 (2)C3ÐN1ÐC10 112.6 (2)N1ÐC2ÐC11 112.9 (2)O3ÐC3ÐN1 123.9 (2)O3ÐC3ÐC4 128.5 (2)N1ÐC3ÐC4 107.5 (2)C3ÐC4ÐC5 130.5 (2)C3ÐC4ÐC9 108.0 (2)C4ÐC9ÐC10 109.5 (2)C8ÐC9ÐC10 129.9 (2)C3ÐN1ÐC2ÐC1A ÿ95.3 (9) C3ÐN1ÐC2ÐC1B ÿ95.8 (11)Table 2Hydrogen-bonding geometry (AÊ , ) for (I).Cg is the centroid of the C4±C9 ring.DÐH  A DÐH H  A D  A DÐH  AO1AÐH1A  O3i 1.06 1.54 2.582 (13) 165O1BÐH1B  O3i 0.98 1.74 2.640 (12) 152C7ÐH7  O2Aii 0.93 2.49 3.231 (11) 136C7ÐH7  O2Bii 0.93 2.66 3.49 (2) 149C8ÐH8  Cg1ii 0.93 2.74 3.466 (3) 136C10ÐH10A  O3iii 0.97 2.49 3.335 (3) 146Symmetry codes: (i) 1ÿ x; yÿ 12; 12ÿ z; (ii) 12 x; 12ÿ y; 1ÿ z; (iii) 1 x; y; z.organic compounds622 Gallagher and Brady  Two isomers of C13H15NO3 Acta Cryst. (2000). C56, 619±622Data collectionEnraf±Nonius CAD-4 diffract-ometer!/2 scans5259 measured re¯ections2575 independent re¯ections2059 re¯ections with I > 2(I)Rint = 0.014max = 27h = ÿ7! 7k = ÿ12! 12l = ÿ13! 133 standard re¯ectionsfrequency: 120 minintensity decay: <1%Re®nementRe®nement on F 2R[F 2 > 2(F 2)] = 0.048wR(F 2) = 0.112S = 1.0162575 re¯ections310 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.0711P)2]where P = (Fo2 + 2Fc2)/3(/)max < 0.001max = 0.36 e AÊÿ3min = ÿ0.31 e AÊ ÿ3Extinction correction: SHELXL97(Sheldrick, 1997)Extinction coef®cient: 0.022 (8)For both compounds, all atoms bound to C were treated as riding,with the SHELXL97 (Sheldrick, 1997) defaults for CÐH distancesand with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) forthe remainder. For (I), the H-atom sites of OÐH were located fromdifference Fourier maps in the penultimate stages of re®nement andwere included at these positions in the calculations, with OÐHdistances of 1.07 and 0.98 AÊ , while for (II), the H atom bound to Owas located from a difference Fourier map and subsequently treatedas a rigid rotating group, with Uiso(H) = 1.5Ueq(O). The absolutestructures of (I) and (II) were not reliably determined by our X-rayanalysis, but they can be inferred from the known absolute con®g-urations of the l-norvaline and l-valine used in the synthesis of (I)and (II), respectively.For both compounds, data collection: CAD-4-PC Software (Enraf±Nonius, 1992); cell re®nement: CAD-4-PC Software; data reduction:NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure:SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:NRCVAX96 and SHELXL97; molecular graphics: ORTEPIII(Burnett & Johnson, 1996), ORTEX (McArdle, 1995) and PLATON(Spek, 1998); software used to prepare material for publication:NRCVAX96, SHELXL97 and PREP8 (Ferguson, 1998).JFG thanks the Research and Postgraduate Committee ofDublin City University for funding of research visits to theUniversity of Guelph (1995±1998), and Professor GeorgeFerguson for use of his diffractometer and computer system.Supplementary data for this paper are available from the IUCr electronicarchives (Reference: GD1085). Additional ®gures are also available.Services for accessing these data are described at the back of the journal.ReferencesAllin, S. M., Hodkinson, C. C. & Taj, N. (1996). Synlett, pp. 781±782.Brady, F., Gallagher, J. F. & Kenny, P. T. M. (1998). Acta Cryst. C54, 1523±1525.Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. OakRidge National Laboratory, Tennessee, USA.Dalton, J. P., Gallagher, J. F., Kenny, P. T. M. & O'Donohoe, M. (1999). ActaCryst. C55, 126±129.Enraf±Nonius (1992). CAD-4-PC Software. Version 1.1. Enraf±Nonius, Delft,The Netherlands.Ferguson, G. (1998). PREP8. University of Guelph, Canada.Ferguson, G., Gallagher, J. F. & McAlees, A. J. (1995). Acta Cryst. C51, 454±458.Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl.Cryst. 22, 384±387.Gallagher, J. F., Brady, F. & Murphy, C. (2000). Acta Cryst. C56, 365±368.Gallagher, J. F., Kenny, P. T. M. & Sheehy, M. J. (1999). Acta Cryst. C55, 1257±1260.Gallagher, J. F. & Murphy, C. (1999). Acta Cryst. C55, 2167±2169.Kundu, N. G., Khan, M. W., Guha, S. & Mukherjee, A. K. (1999). Acta Cryst.C55, 239±241.McArdle, P. (1995). J. Appl. Cryst. 28, 65.McNab, H., Parsons, S. & Shannon, D. A. (1997). Acta Cryst. C53, 1098±1099.Mukherjee, A. K., Guha, S., Khan, M. W., Kundu, N. G. & Helliwell, M. (2000).Acta Cryst. C56, 85±87.Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G. & Taylor,R. (1994). Structure Correlation, Vol. 2, edited by H.-B. BuÈ rgi & J. D. Dunitz.Weinheim: VCH.Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University ofGoÈ ttingen, Germany.Spek, A. L. (1998). PLATON. University of Utrecht, The Netherlands.Weigand, C., Feigel, M. & Landgrafe, C. (1998). J. Chem. Soc. Chem. Commun.pp. 679±680.Table 3Selected geometric parameters (AÊ , ) for (II).O1AÐC1A 1.317 (4)O2AÐC1A 1.194 (4)O3AÐC3A 1.229 (4)N1AÐC2A 1.460 (4)N1AÐC3A 1.344 (4)N1AÐC10A 1.456 (4)C1AÐC2A 1.540 (4)C2AÐC11A 1.535 (5)C3AÐC4A 1.472 (4)C9AÐC10A 1.497 (5)O1BÐC1B 1.311 (4)O2BÐC1B 1.202 (4)O3BÐC3B 1.235 (3)N1BÐC2B 1.456 (4)N1BÐC3B 1.348 (4)N1BÐC10B 1.463 (4)C1BÐC2B 1.530 (4)C2BÐC11B 1.537 (4)C3BÐC4B 1.465 (4)C9BÐC10B 1.489 (5)C2AÐN1AÐC3A 124.0 (3)C2AÐN1AÐC10A 122.3 (3)C3AÐN1AÐC10A 113.3 (3)O1AÐC1AÐO2A 124.2 (3)O1AÐC1AÐC2A 110.7 (3)O2AÐC1AÐC2A 125.1 (3)N1AÐC2AÐC1A 108.6 (2)O3AÐC3AÐN1A 124.4 (3)O3AÐC3AÐC4A 129.2 (3)N1AÐC10AÐC9A 102.0 (3)C2BÐN1BÐC3B 124.2 (2)C2BÐN1BÐC10B 122.7 (2)C3BÐN1BÐC10B 112.8 (2)O1BÐC1BÐO2B 123.1 (3)O1BÐC1BÐC2B 111.4 (3)O2BÐC1BÐC2B 125.5 (3)N1BÐC2BÐC1B 108.9 (2)O3BÐC3BÐN1B 123.9 (3)O3BÐC3BÐC4B 129.1 (3)N1BÐC10BÐC9B 102.5 (2)O1AÐC1AÐC2AÐC11A 172.8 (3)N1AÐC2AÐC11AÐC12A ÿ43.6 (4)C1AÐC2AÐC11AÐC13A 69.1 (4)C3AÐN1AÐC2AÐC1A 57.3 (4)O1BÐC1BÐC2BÐC11B 168.6 (3)N1BÐC2BÐC11BÐC12B ÿ52.0 (3)C1BÐC2BÐC11BÐC13B 59.2 (4)C3BÐN1BÐC2BÐC1B 60.7 (4)Table 4Hydrogen-bonding geometry (AÊ , ) for (II).DÐH  A DÐH H  A D  A DÐH  AO1AÐH1A  O3Bi 0.82 1.93 2.642 (3) 145C5AÐH5A  O2B 0.93 2.68 3.529 (5) 152C10AÐH10B  O3Aii 0.97 2.43 3.314 (4) 151C10AÐH10A  O3Biii 0.97 2.58 3.477 (4) 153O1BÐH1B  O3A 0.82 1.87 2.634 (3) 154C5BÐH5B  O2Aiv 0.93 2.86 3.714 (5) 153C10BÐH10C  O3Av 0.97 2.56 3.455 (4) 154C10BÐH10D  O3Bv 0.97 2.46 3.283 (4) 143Symmetry codes: (i) x; 1 y; z; (ii) xÿ 1; y; z; (iii) xÿ 1; 1 y; z; (iv) x; yÿ 1; z; (v)1 x; y; z.

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O-H...O, C-H...O and C-H...[pi]arene intermolecular 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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O-H...O, C-H...O and C-H...[pi]arene intermolecular 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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