N,N′-Diphenyl­but-2-enediamide

B Thimme Gowda; Sabine Foro; K Shakuntala; Hartmut Fuess

doi:10.1107/S1600536810051330

. 2010 Dec 11;67(Pt 1):o117. doi: 10.1107/S1600536810051330

N,N′-Diphenylbut-2-enediamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, K Shakuntala ^a, Hartmut Fuess ^b

PMCID: PMC3050154 PMID: 21522628

Abstract

In the title compound, C₁₆H₁₄N₂O₂, the conformations of the N—H and C=O bonds in the C—NH—CO—CH =CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other. The two phenyl rings make an interplanar angle of 41.2 (1)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, intermolecular N—H⋯O hydrogen bonding links the molecules into infinite chains along the a axis.

Related literature

For related structures, see: Gowda, Foro et al. (2010 ▶); Gowda, Tokarčík et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M _r = 266.29
Orthorhombic,
a = 6.604 (1) Å
b = 13.358 (2) Å
c = 15.474 (2) Å
V = 1365.1 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 299 K
0.35 × 0.30 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3656 measured reflections
1422 independent reflections
1339 reflections with I > 2σ(I)
R _int = 0.117
3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.100
S = 1.06
1422 reflections
188 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 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/S1600536810051330/ng5082sup1.cif

e-67-0o117-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051330/ng5082Isup2.hkl

e-67-0o117-Isup2.hkl^{(70.2KB, 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⋯O2ⁱ	0.86 (2)	2.04 (2)	2.884 (3)	167 (2)
N2—H2N⋯O1	0.91 (2)	1.77 (2)	2.671 (3)	167 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

KS 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 moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of substitutions on the structures of this class of compounds (Gowda, Foro et al., 2010; Gowda, Tokarčík et al., 2010), the crystal structure of N,N-bis(phenyl)-maleamide has been determined (I) (Fig. 1).

In the structure, the conformations of N—H and C=O bonds in both the amide groups of the C—NH—CO—CH ═CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other, while one of them is syn to the adjacent C—H bond and the other is anti to its adjacent C—H bond. Further, C1—N1—C7—C8 and C11—N2—C10—C9 segments are nearly linear and so also the C1—N1—C7—O1 and C11—N2—C10—O2 segments. The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are 174.4 (3)° and -4.9 (4)°, respectively, while those of C12—C11—N2—C10 and C16—C11—N2—C10 are 40.4 (4)° and -143.9 (3)°.

The two phenyl rings in (I) make an interplanar angle of 41.2 (1)°. while the two benzene rings (C1 to C6 and C11 to C16) make the dihedral angles of 8.0 (1)° and 38.3 (1)°, respectively, with the central amide group (N1—C7—C8—C9—C10—N2).

The crystal structure (Fig. 2) exhibits both the intramolecular and intermolecular N–H···O hydrogen bonds (Table 1). The latter link the molecules into chains.

Experimental

A mixture of maleic acid (0.2 mol) and phosphorous oxy chloride (0.3 mol) were refluxed for 3 hrs on a water bath at 95° C. The aniline was added dropwise with stirring and continuing heating for about 30 min. It was later kept aside for 12 hrs for completion of the reaction. The reaction mixture was then added to ice. The precipitated product was washed with water, dilute HCl, dilute NaOH and again with water. The product was filtered, dried and recrystallized from DMF.

Prism like orange single crystals of the title compound used in X-ray diffraction studies were obtained by a slow evaporation of its DMF solution at room temperature.