N,N′-Bis(3-chloro­phen­yl)succinamide

B S Saraswathi; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811010440

. 2011 Mar 26;67(Pt 4):o966. doi: 10.1107/S1600536811010440

N,N′-Bis(3-chlorophenyl)succinamide

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

PMCID: PMC3099800 PMID: 21754229

Abstract

The complete molecule of the title compound, C₁₆H₁₄Cl₂N₂O₂, is generated by crystallographic inversion symmetry. The dihedral angle between the benzene ring and the NH—C(O)—C fragment is 32.8 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds into [100] chains.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶) and of N-(substitutedphenyl)-p-substituted-benzenesulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C₁₆H₁₄Cl₂N₂O₂
M _r = 337.19
Monoclinic,
a = 8.3412 (8) Å
b = 9.6501 (9) Å
c = 9.5485 (9) Å
β = 91.319 (9)°
V = 768.39 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.847, T _max = 0.919
2574 measured reflections
1535 independent reflections
1253 reflections with I > 2σ(I)
R _int = 0.009

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.07
1535 reflections
103 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 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 datablocks I, global. DOI: 10.1107/S1600536811010440/ds2100sup1.cif

e-67-0o966-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010440/ds2100Isup2.hkl

e-67-0o966-Isup2.hkl^{(75.7KB, 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
N1—H1N⋯O1ⁱ	0.81 (2)	2.10 (2)	2.8946 (19)	166 (2)

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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 a part of studying the substituent effects on the structures of this class of compounds(Gowda et al., 2000, 2005, 2007; Saraswathi et al., 2011), in the present work, the structure of N,N-bis(3-chlorophenyl)-succinamide (I) has been determined (Fig.1). The conformations of N—H and C=O bonds in the C—NH—C(O)—C segments are anti to each other and the amide O atoms are anti to the H atoms attached to the adjacent C atoms. Further, conformations of the N—H bonds in the amide fragments are anti to the meta-chloro groups in the adjacent benzene rings, similar to the anti conformations observed with respect to the ortho-methyl groups in N,N-bis(2-methylphenyl)- succinamide (II) (Saraswathi et al., 2011). The dihedral angle between the benzene ring and the NH—C(O)—CH₂ segment in the two halves of the molecule is 32.8 (1)°, compared to the value of 62.1 (2)° in (II).

Further, C1—N1—C7—C8 and C1a—N1a—C7a—C8a segments in (I) are nearly linear and so also the C1—N1—C7—O1 and C1a—N1a—C7a—O1a segments, similar to those observed in (II). The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are -35.0 (3)° and 147.5 (2)°, in contrast to the values of -64.0 (4)° and 117.6 (3)° in (II).

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

Experimental

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise 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 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-chloroaniline 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,N-bis(3-chlorophenyl)- succinamide was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from a mixture of acetone and chloroform. The purity of the compound was checked by elemental analysis, and characterized by its infrared and NMR spectra.

Rod like colorless single crystals used in the X-ray diffraction studies were were grown in a mixture of acetone and chloroform at room temperature.