N-Phenyl­succinamic acid

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

doi:10.1107/S160053681005364X

. 2011 Jan 8;67(Pt 2):o249. doi: 10.1107/S160053681005364X

N-Phenylsuccinamic acid

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

PMCID: PMC3051503 PMID: 21522943

Abstract

In the crystal structure of the title compound, C₁₀H₁₁NO₃, the conformations of N—H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent –CH₂ groups. The C=O and O—H bonds of the acid group are in syn positions with respect to each other. In the crystal, the molecules are packed into infinite chains along the a axis through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures of anilides, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For the packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C₁₀H₁₁NO₃
M _r = 193.20
Monoclinic,
a = 4.986 (1) Å
b = 25.108 (4) Å
c = 7.895 (2) Å
β = 103.18 (2)°
V = 962.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.44 × 0.14 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.958, T _max = 0.986
3269 measured reflections
1791 independent reflections
1033 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.135
S = 0.99
1791 reflections
133 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S160053681005364X/bq2265sup1.cif

e-67-0o249-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005364X/bq2265Isup2.hkl

e-67-0o249-Isup2.hkl^{(88.2KB, 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	0.85 (2)	2.22 (2)	3.041 (3)	161 (2)
O3—H3O⋯O2ⁱⁱ	0.88 (2)	1.80 (2)	2.671 (2)	177 (3)

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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

As a part of studying the effect of ring and side chain substitutions on the crystal structures of anilides (Gowda et al., 2009; 2010a,b), the crystal structure of N-(phenyl)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-(2-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) and N-(3-chlorophenyl)succinamic acid (V) (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), (IV) and (V).

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 aniline (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 aniline. The resultant solid N-(phenyl)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.

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