3-[(3,4-Dichloro­phen­yl)amino­carbon­yl]propionic acid monohydrate

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

doi:10.1107/S1600536809024519

. 2009 Jul 1;65(Pt 8):o1722. doi: 10.1107/S1600536809024519

3-[(3,4-Dichlorophenyl)aminocarbonyl]propionic acid monohydrate

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

PMCID: PMC2977205 PMID: 21583439

Abstract

In the crystal structure of the title compound, C₁₀H₉Cl₂NO₃·H₂O, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to the H atoms of adjacent –CH₂ groups. In the crystal, the molecules are linked into a three-dimensional network through N—H⋯O and O—H⋯O intermolecular hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009a ▶,b ▶,c ▶). For hydrogen bonds involving carboxylic acids, see: Jagannathan et al. (1994 ▶); Leiserowitz (1976 ▶). For the modeling of water H atoms, see: Nardelli (1999 ▶).

Experimental

Crystal data

C₁₀H₉Cl₂NO₃·H₂O
M _r = 280.10
Monoclinic,
a = 9.5634 (9) Å
b = 7.4527 (7) Å
c = 17.292 (2) Å
β = 104.35 (2)°
V = 1194.0 (2) Å³
Z = 4
Cu Kα radiation
μ = 4.95 mm⁻¹
T = 299 K
0.55 × 0.50 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.098, T _max = 0.138
2508 measured reflections
2129 independent reflections
2052 reflections with I > 2σ(I)
R _int = 0.072
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.212
S = 1.08
2129 reflections
167 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.69 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/S1600536809024519/ci2838sup1.cif

e-65-o1722-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024519/ci2838Isup2.hkl

e-65-o1722-Isup2.hkl^{(104.7KB, 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
O2—H2O⋯O4ⁱ	0.88 (3)	1.79 (3)	2.672 (4)	177 (5)
N1—H1N⋯O3ⁱⁱ	0.84 (3)	2.11 (3)	2.941 (4)	168 (4)
O4—H41⋯O1ⁱⁱⁱ	0.82 (3)	2.11 (4)	2.894 (4)	162 (5)
O4—H42⋯O1^iv	0.84 (3)	2.09 (3)	2.881 (4)	156 (5)

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

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 structures of aromatic amides (Gowda et al., 2009a,b,c), the crystal structure of N-(3,4-dichlorophenyl)succinamic acid monohydrate (I), systematic name: 3-[(3,4-dichloro)-aminocarbonyl]propionic acid monohydrate has been determined. The conformation of the N—H bond is anti to both the 3-chloro substituent in the aromatic ring and the C═O bond in the amide segment of the structure. Further, the amide O atom and the carbonyl O atom of the acid segment are anti to each other and are also anti to H atoms attached to the adjacent C atoms (Fig.1). Further, C═O and O—H bonds of the acid group are syn to each other, contrary to the anti position observed in 3-[(3,5-dichloro)-aminocarbonyl]propionic acid (Gowda et al., 2009c). The observed anti position with the latter may be due to the hydrogen bond donated to the amide carbonyl group by the acid segment, which is prevented in the present structure due to the H-bonding effect of hydration. The N—H···O and O—H···O intermolecular hydrogen bonds link the molecules into a three-dimensional network (Table 1 and 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 (0.02 mol) in toluene (25 ml) was treated dropwise with the solution of 3,4-dichloroaniline (0.02 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 1 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 3,4-dichloroaniline. The resultant solid N-(3,4-dichlorophenyl)-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. Single crystals used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation at room temperature.