N-(3-Chloro­phen­yl)-N′-(3-methyl­phen­yl)succinamide

B S Saraswathi; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811028121

. 2011 Jul 23;67(Pt 8):o2077. doi: 10.1107/S1600536811028121

N-(3-Chlorophenyl)-N′-(3-methylphenyl)succinamide

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

PMCID: PMC3213520 PMID: 22091099

Abstract

The asymmetric unit of the title compound, C₁₇H₁₇ClN₂O₂, contains one half-molecule with a center of inversion at the mid-point of the central C—C bond. The amide N—H group is anti to the meta-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH—C(O)—CH₂ segment is 43.5 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the a axis. The methyl group and the Cl atom occupy the same position and were treated in a disorder model with site-occupation factors of 0.5 each.

Related literature

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2007 ▶); Saraswathi et al. (2011a ▶,b ▶) and on the structures of N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ▶). For similar structures, see: Pierrot et al. (1984 ▶). For restrained geometry, see: Nardelli (1999 ▶).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₂
M _r = 316.78
Triclinic,
a = 4.840 (1) Å
b = 5.560 (1) Å
c = 14.752 (3) Å
α = 93.47 (2)°
β = 91.39 (2)°
γ = 97.71 (2)°
V = 392.46 (13) Å³
Z = 1
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.44 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.897, T _max = 0.980
2451 measured reflections
1567 independent reflections
1249 reflections with I > 2σ(I)
R _int = 0.010

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.130
S = 0.99
1567 reflections
110 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 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/S1600536811028121/wm2508sup1.cif

e-67-o2077-sup1.cif^{(14.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028121/wm2508Isup2.hkl

e-67-o2077-Isup2.hkl^{(77.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028121/wm2508Isup3.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—H1⋯O1ⁱ	0.86	2.05	2.894 (2)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures of this class of compounds (Bhat & Gowda, 2000; Gowda et al., 2007; Jayalakshmi & Gowda, 2004; Saraswathi et al., 2011a,b), in the present work, the structure of N-(3-chlorophenyl),N-(3-methylphenyl)- succinamide, (I), has been determined (Fig.1). The asymmetric unit of (I) contains half a molecule with a center of inversion at the mid-point of the central C—C bond, similar to that observed in bis(2-chlorophenylaminocarbonylmethyl)disulfide, (II), (Pierrot et al., 1984), N,N-bis(3-chlorophenyl)-succinamide, (III), (Saraswathi et al., 2011a) and N,N-bis(3-methylphenyl)-succinamide dihydrate, (IV), (Saraswathi et al., 2011b).

The conformations of the amide O atoms are anti to the H atoms attached to the adjacent C atoms. Further, the conformations of the N—H bonds in the amide fragments are anti to the meta-chloro/methyl groups in the adjacent benzene rings, similar to the anti conformations observed with respect to the meta-chloro groups in (III) and meta-methyl groups in (IV).

Further, the C1—N1—C7—C8 and C1a—N1a—C7a—C8a segments in (I) are nearly planar and so also the C1—N1—C7—O1 and C1a—N1a—C7a—O1a segments, similar to those observed in (III) and (IV). The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are -43.2 (4)° and 138.6 (3)°, in contrast to the values of -35.0 (3)° and 147.5 (2)° in (III), and 5.4 (9)° and -173.6 (6)° in (IV).

The dihedral angle between the benzene ring and the NH—C(O)—CH₂ segment is 43.5 (1)°, compared to the values of 62.1 (2)° in (III) and 5.6 (4)° in (IV).

The packing of the molecules in the crystal is accomplished by N—H···O hydrogen bonds (Table 1) that lead is shown in Fig. 2.

Experimental

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated dropwise with 3-chloroaniline (0.01 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for 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 unreacted 3-chloroaniline. The resultant solid N-(3-chlorophenyl)-succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to a constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The N-(3-chlorophenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 3-methylaniline at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N-(3-chlorophenyl), N-(3-methylphenyl)-succinamide was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to a constant melting point from a mixture of acetone and toluene (3:1 v/v). The compound was characterized by its infrared and NMR spectra.

Prism-like colorless single crystals used in X-ray diffraction studies were grown in a mixture of acetone and toluene (3:1 v/v) at room temperature.