N-(4-Chloro-3-nitro­phen­yl)succinamic acid

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812008720

. 2012 Mar 3;68(Pt 4):o951. doi: 10.1107/S1600536812008720

N-(4-Chloro-3-nitrophenyl)succinamic acid

U Chaithanya ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3343932 PMID: 22590013

Abstract

In the title compound, C₁₀H₉ClN₂O₅, the nitro group is significantly twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 27.4 (6)°]. In the crystal, molecules are linked into centrosymmetric dimers via pairs of O—H⋯O hydrogen bonds. These dimers are further linked by N—H⋯O hydrogen bonds into double chains running along the a axis.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000 ▶); Chaithanya et al. (2012 ▶), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶), on N-chloroarylamides, see: Gowda et al. (2003 ▶); Jyothi & Gowda (2004 ▶) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₀H₉ClN₂O₅
M _r = 272.64
Monoclinic,
a = 4.8089 (8) Å
b = 10.278 (1) Å
c = 23.062 (3) Å
β = 90.69 (2)°
V = 1139.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.44 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.861, T _max = 0.966
4342 measured reflections
2305 independent reflections
1601 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.169
S = 1.05
2305 reflections
169 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.41 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 datablock(s) I, global. DOI: 10.1107/S1600536812008720/bt5832sup1.cif

e-68-0o951-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008720/bt5832Isup2.hkl

e-68-0o951-Isup2.hkl^{(113.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008720/bt5832Isup3.cml

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)	2.28 (3)	3.006 (3)	144 (3)
O3—H3O⋯O2ⁱⁱ	0.83 (2)	1.84 (2)	2.667 (3)	176 (4)

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

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under UGC–BSR one-time grant to faculty.

supplementary crystallographic information

Comment

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Chaithanya et al., 2012), N-(aryl)-methanesulfonamides (Gowda et al., 2007); N-chloroarylsulfonamides (Gowda et al., 2003; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(4-Chloro-3-nitrophenyl)succinamic acid has been determined (Fig. 1). The conformations of the N—H and the C=O bonds in the amide segment are anti to each other. But the N—H bond is syn to the meta–nitro group. The conformations of the amide C═O and the carboxyl C═O of the acid segment are anti to each other and both are anti to the H atoms on the adjacent –CH₂ groups. Furthermore, the C═O and O—H bonds of the acid group are in syn position to each other, in contrast to the anti positions observed in N-(4-Chloro-3-nitro- phenyl)maleamic acid (I) (Chaithanya et al., 2012).

The dihedral angle between the phenyl ring and the amide group in the title compound is 31.8 (2)°, compared to the value of 11.5 (3)° in (I).

In the structure, the O—H···O and N—H···O intermolecular hydrogen bonds link the molecules into double chains running along the a axis (Table 1, Fig. 2).

Experimental

Succinic anhydride (0.025 mol) in toluene (25 ml) was treated dropwise with 4-chloro-3-nitroaniline (0.025 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 30 min and set aside for an additional 30 min at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 4-chloro-3-nitroaniline. The resultant solid N-(4-Chloro-3-nitrophenyl)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 and characterized by its infrared spectra.

Rod like colorless single crystals of the title compound used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation of the solvent (0.5 g in about 30 ml of ethanol) at room temperature.