N-(3-Chloro-2-methyl­phen­yl)succinamic acid

B Thimme Gowda; Sabine Foro; U Chaithanya

doi:10.1107/S1600536812022763

. 2012 May 23;68(Pt 6):o1869. doi: 10.1107/S1600536812022763

N-(3-Chloro-2-methylphenyl)succinamic acid

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

PMCID: PMC3379433 PMID: 22719631

Abstract

In the title compound, C₁₁H₁₂ClNO₃, the dihedral angle between the benzene ring and the amide group is 44.9 (2)°. In the crystal, molecules form inversion dimers via pairs of O—H⋯O hydrogen bonds. These dimers are further linked into sheets parallel to (013) via N—H⋯O hydrogen bonds.

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 ▶), of N-chloroarylamides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983 ▶), Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₁H₁₂ClNO₃
M _r = 241.67
Triclinic,
a = 4.7672 (9) Å
b = 6.297 (1) Å
c = 19.135 (3) Å
α = 87.24 (1)°
β = 83.95 (1)°
γ = 88.28 (2)°
V = 570.37 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.881, T _max = 0.994
3270 measured reflections
2072 independent reflections
1578 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.127
S = 1.20
2072 reflections
152 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 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/S1600536812022763/bt5924sup1.cif

e-68-o1869-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022763/bt5924Isup2.hkl

e-68-o1869-Isup2.hkl^{(101.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022763/bt5924Isup3.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
O3—H3O⋯O2ⁱ	0.83 (2)	1.84 (2)	2.666 (3)	176 (5)
N1—H1N⋯O1ⁱⁱ	0.83 (2)	2.10 (2)	2.905 (3)	163 (3)

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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 theUGC–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-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-Chloro-2-methylphenyl)succinamic acid has been determined (Fig. 1). The conformation of the N—H bond in the amide segment is syn to the ortho–methyl and meta–Cl in the benzene ring, in contrast to the anti conformation observed between the N—H bond and the meta–Cl in N-(3-chloro-4-methylphenyl)- succinamic acid (I) (Chaithanya et al., 2012).

Further, the conformations of the amide oxygen and the carboxyl oxygen of the acid segments are anti to each other and both are anti to the H atoms on the adjacent –CH₂ groups.

The C═O and O—H bonds of the acid groups are in syn position to each other, similar to that observed in (I).

The dihedral angle between the phenyl ring and the amide group is 44.9 (2)°, compared to the values of 40.6 (2)° and 44.9 (3)° in the two independent molecules of (I).

In the crystal, the molecules form centrosymmetric dimers via O-H···O hydrogen bonds. These dimers are further linked into sheets parallel to (0 1 3) via intermolecular N–H···O hydrogen bonds. (Table 1, Fig.2).

Experimental

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of 3-chloro-2-methylaniline (0.01 mole) also in toluene (20 ml) 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 3-chloro-2-methyl-aniline. The resultant (the title compound) 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 spectrum.

Plate like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.