N-(2,4,6-Trimethyl­phen­yl)succinamic acid

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

doi:10.1107/S1600536809029791

. 2009 Jul 31;65(Pt 8):o2056. doi: 10.1107/S1600536809029791

N-(2,4,6-Trimethylphenyl)succinamic acid

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

PMCID: PMC2977192 PMID: 21583718

Abstract

The amide bond in the title compound {systematic name: 3-[(2,4,6-trimethylphenyl)aminocarbonyl]propionic acid}, C₁₃H₁₇NO₃, has a trans conformation. In the crystal, two molecules form a centrosymmetric dimer connected by pairs of O—H⋯O hydrogen bonds. Intermolecular N—H⋯O hydrogen bonds link the dimers into a three dimensional network.

Related literature

For related structures, see: Gowda et al. (2009a ▶,b ▶,c ▶); Jagannathan et al. (1994 ▶). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C₁₃H₁₇NO₃
M _r = 235.28
Triclinic,
a = 4.7646 (4) Å
b = 10.859 (1) Å
c = 13.111 (2) Å
α = 70.217 (8)°
β = 86.158 (8)°
γ = 79.351 (8)°
V = 627.31 (12) Å³
Z = 2
Cu Kα radiation
μ = 0.72 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 = 0.692, T _max = 0.945
3109 measured reflections
2234 independent reflections
1918 reflections with I > 2σ(I)
R _int = 0.014
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.145
S = 1.05
2234 reflections
182 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 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/S1600536809029791/bt5016sup1.cif

e-65-o2056-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029791/bt5016Isup2.hkl

e-65-o2056-Isup2.hkl^{(109.8KB, 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	0.86 (2)	2.10 (2)	2.9368 (18)	163.6 (19)
O2—H2O⋯O3ⁱⁱ	0.88 (3)	1.80 (3)	2.679 (2)	172 (3)

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

Acknowledgments

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

supplementary crystallographic information

Comment

The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of ring and side chain substitutions on the structures of this class of compounds (Gowda et al., 2009a,b,c), the crystal structure of N-(2,4,6-trimethylphenyl)-succinamic acid (I) {systematic name: 3-[(2,4,6-trimethylphenyl)-aminocarbonyl]propionic acid} has been determined. The conformations of N—H and C=O bonds in the amide segment of the structure are trans to each other (Fig.1). But the conformations of the amide O atom and the carbonyl O atom of the acid segment are cis to each other Further, the conformations of the C(O)—C bonds in the N—CO—CH₂—CH₂—C(O)—OH segment have "trans" and "gauche" torsions with the adjacent C—H bonds.

The C=O and O—H bonds of the acid group are in syn position to each other, similar to that observed in the crystal structures of N-(2,6-dimethylphenyl)- succinamic acid (Gowda et al., 2009b) and N-(2-chlorophenyl)succinamic acid (Gowda et al., 2009a) but in contrast to the anti positions observed in the structure of N-(3,5-dichlorophenyl)succinamic acid(Gowda et al., 2009c)

The torsional angles of the groups, C1 - N1 - C7 - C8, N1 - C7 - C8 - C9, C7 - C8 - C9 - C10 and C8 - C9 - C10 - O2 in the side chain are 180.0 (2)°, -160.5 (2)°, 63.5 (2)° and -174.9 (2)°, respectively. The N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules in the structure into supramolecular chains (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 (0.025 mole) in toluene (25 cc) was treated dropwise with the solution of 2,4,6-trimethylaniline(0.025 mole) also in toluene (20 cc) with constant stirring. The resulting mixture was stirred for about one h and set aside for an additional hour at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 2,4,6-trimethylaniline. The resultant solid N-(2,4,6-trimethylphenyl)-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 spectra. The plate like colourless single crystals of the compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.