(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methyl­sulfan­yl)butanoic acid

Abdul Rauf Raza; M Nawaz Tahir; Aisha Saddiqa; Muhammad Danish; M Saeed Iqbal

doi:10.1107/S1600536809028992

. 2009 Jul 25;65(Pt 8):o2002. doi: 10.1107/S1600536809028992

(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methylsulfanyl)butanoic acid

Abdul Rauf Raza ^a, M Nawaz Tahir ^b,^*, Aisha Saddiqa ^a, Muhammad Danish ^a, M Saeed Iqbal ^c

PMCID: PMC2977145 PMID: 21583673

Abstract

The title compound, C₁₃H₁₃NO₄S, the 1,3-dioxoisoindolin-2-yl unit is planar (r.m.s. deviation 0.0192 Å) and is oriented at a dihedral angle of 79.14 (18)° to the carboxylate group. An intramolecular C—H⋯O hydrogen bond leads to the formation of a planar (r.m.s. deviation 0.0419 Å)R(5) ring motif. In the crystal, molecules are connected through O—H⋯O and C—H⋯O hydrogen bonds with R ₂ ²(9) ring motifs into chains extending along the b axis.

Related literature

For the biological activity of isocoumarin and 3,4-dihydroisocoumarin, see: Hill (1986 ▶); Canedo et al. (1997 ▶); Whyte et al. (1996 ▶). For related structures, see: Barooah et al. (2007 ▶); Feeder & Jones (1994 ▶); Rajagopal et al. (2003 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₃NO₄S
M _r = 279.30
Orthorhombic,
a = 6.7923 (6) Å
b = 9.9581 (8) Å
c = 20.0970 (17) Å
V = 1359.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.20 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.969, T _max = 0.985
7865 measured reflections
1864 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 1.06
1864 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028992/pb2001sup1.cif

e-65-o2002-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028992/pb2001Isup2.hkl

e-65-o2002-Isup2.hkl^{(89.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.77 (3)	1.96 (3)	2.673 (3)	154 (3)
C3—H3⋯O2ⁱⁱ	0.9300	2.4200	3.328 (4)	165.00
C9—H9⋯O4	0.96 (3)	2.48 (3)	2.905 (3)	106.4 (18)
C11—H11B⋯O1ⁱⁱⁱ	0.9700	2.5400	3.443 (3)	156.00

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for technical support, respectively.

supplementary crystallographic information

Comment

Isocoumarin and 3,4-dihydroisocoumarin have shown an impressive array of biological activities such as anti-tumor (Hill et al., 1986), anti-leucemic (Canedo et al., 1997) and anti-microbial (Whyte et al., 1996). The titled compound (I, Fig. 1) is an intermediate towards the synthesis of chiral isocoumarin. The biological activity of the title compound and synthesis of its complexes are in progress.

The crystal structures of 2-Phthalimidoethanoic acid monohydrate (Feeder & Jones, 1994), N-Phthaloylglycine (Barooah et al., 2007) and DL-Methioninium trichloroacetate (Rajagopal et al., 2003) have been published which contain the moieties of the title compound.

In the title compound the aromatic ring and heterocyclic ring along with O-atoms of carbonyl groups A (C1—C8/N1/O3/O4), the linear chain B (C9—C11/S1/C12) and the carboxylate group C (O1/C13/O2) are planar. There exists an intramolecular H-bond of type C—H···O completing a planar S(5) ring motif (Bernstein et al., 1995). The value of dihedral angle between A/B, A/C and B/C is 80.04 (7)°, 79.14 (18)° and 20.54 (30)°, respectively. Due to the intermolecular H-bonding (Table 1), the molecules are connected in one dimensional polymeric chains through ring motifs R₂²(9) extending along the b-axis.

Experimental

The methionine (2.0 g, 13.4 mmol) and phthalic anhydride (2.13 g, 14.38 mmol) were added to a flask with constant stirring at 423 K for 2 h. The reaction mixture was brought to room temperature and the crystalline phthallic anhydride on the walls of the flask were removed. The solid crude product was purified by crystallization from ethanol/water (7:3) that afforded colorless prisms of the title compound (I).

Yield 81%.