N-(4-Methyl­phen­yl)succinamic acid

B S Saraswathi; Sabine Foro; B Thimme Gowda; Hartmut Fuess

doi:10.1107/S1600536810053298

. 2010 Dec 24;67(Pt 1):o227. doi: 10.1107/S1600536810053298

N-(4-Methylphenyl)succinamic acid

B S Saraswathi ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*, Hartmut Fuess ^b

PMCID: PMC3050143 PMID: 21522726

Abstract

In the title compound, C₁₁H₁₃NO₃, the conformations of the N—H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide and carbonyl O atoms of the acid segment are also anti to the adjacent –CH₂ groups. The C=O and O—H bonds of the acid group are syn to each other. In the crystal, molecules are packed into infinite chains along the b axis through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitution on the solid state geometry of anilides, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C₁₁H₁₃NO₃
M _r = 207.22
Triclinic,
a = 4.960 (1) Å
b = 8.090 (2) Å
c = 13.893 (2) Å
α = 83.52 (2)°
β = 80.08 (2)°
γ = 78.15 (1)°
V = 535.70 (19) Å³
Z = 2
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 299 K
0.55 × 0.25 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.674, T _max = 0.940
2515 measured reflections
1888 independent reflections
1533 reflections with I > 2σ(I)
R _int = 0.024
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.194
S = 1.06
1888 reflections
143 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053298/ds2081sup1.cif

e-67-0o227-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053298/ds2081Isup2.hkl

e-67-0o227-Isup2.hkl^{(92.9KB, 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
N1—H1N⋯O1ⁱ	0.84 (2)	2.15 (2)	2.979 (2)	175 (3)
O3—H3O⋯O2ⁱⁱ	0.84 (2)	1.84 (2)	2.681 (3)	171 (4)

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

Acknowledgments

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

In the present work, as a part of studying the effect of ring and side chain substitutions on the solid state geometry of anilides (Gowda et al., 2009, 2010a, b), the crystal structure of N-(4-methylphenyl)- succinamic acid (I) has been determined. The conformations of N—H and C=O bonds in the amide segment are anti to each other. The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are also anti to each other, similar to that observed in N-(4-Chlorophenyl)succinamic acid (II) (Gowda et al., 2009) and N-(2-methylphenyl)-succinamic acid (III)(Gowda et al., 2010b). but contrary to the syn conformation observed in N-(3-methylphenyl)-succinamic acid (IV) (Gowda et al., 2010a).

Further, the conformation of both the C=O bonds are anti to the H atoms of their adjacent –CH₂ groups (Fig. 1) and the C=O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (II), (III) and (IV).

The N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules into infinite chains in the structure (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Experimental

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of p-toluidine (0.01 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one h and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted p-toluidine. The resultant solid N-(4-methylphenyl)- succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The plate like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.