N-(4-Chloro­phen­yl)succinamic acid

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

doi:10.1107/S160053680902649X

. 2009 Jul 11;65(Pt 8):o1827. doi: 10.1107/S160053680902649X

N-(4-Chlorophenyl)succinamic acid

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

PMCID: PMC2977089 PMID: 21583529

Abstract

In the title compound, C₁₀H₁₀ClNO₃, the conformation of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and further, they are anti to the H atoms of their adjacent –CH₂ groups. The C=O and O—H bonds of the acid group are in the syn position relative to each other. In the crystal, molecules are packed into infinite chains through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For our study of the effect of ring and side-chain substitution on the solid-state geometry of anilides, see: Gowda et al. (2009a ▶,b ▶,c ▶). For the 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

C₁₀H₁₀ClNO₃
M _r = 227.64
Monoclinic,
a = 15.908 (1) Å
b = 4.8778 (4) Å
c = 14.286 (1) Å
β = 109.787 (6)°
V = 1043.09 (13) Å³
Z = 4
Cu Kα radiation
μ = 3.16 mm⁻¹
T = 299 K
0.55 × 0.43 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.265, T _max = 0.623
3006 measured reflections
1837 independent reflections
1643 reflections with I > 2σ(I)
R _int = 0.026
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.121
S = 1.04
1837 reflections
143 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 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/S160053680902649X/bv2121sup1.cif

e-65-o1827-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902649X/bv2121Isup2.hkl

e-65-o1827-Isup2.hkl^{(90.5KB, 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	0.819 (17)	2.117 (17)	2.931 (2)	173 (2)
O2—H2O⋯O3ⁱⁱ	0.85 (3)	1.85 (3)	2.693 (2)	179 (3)

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As a part of studying the effect of ring and side chain substitutions on the solid state geometry of anilides (Gowda et al., 2009a,b,c), we report herein the crystal structure of N-(4-chlorophenyl)succinamic acid (I). The conformations of N—H and C=O bonds in the amide segment are anti to each other and the conformation of the amide oxygen and the carbonyl oxygen of the acid segment are also anti to each other and further, they are anti to the H atoms of their adjacent –CH₂ groups (Fig. 1), similar to that observed in N-(4-chlorophenyl)succinamate (Gowda et al., 2009a) and N-(2-chlorophenyl)succinamic acid (Gowda et al., 2009b). The C=O and O—H bonds of the acid group are in syn position to each other. The N—H···O and O—H···O intermolecular hydrogen bonds pack the mpolecules 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 (2.5 g) in toluene (25 cc) was treated dropwise with the solution of 4-chloroaniline (2.5 g) also in toluene (20 cc) with constant stirring. The resulting mixture was stirred for about one hour 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 4-chloroaniline. The resultant solid N-(4-chlorophenyl)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 single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.