(Z)-2-Amino-3-[(E)-benzyl­ideneamino]but-2-enedinitrile

G Varsha; V Arun; Manju Sebastian; P Leeju; Digna Varghese; K K M Yusuff

doi:10.1107/S1600536809010873

. 2009 Mar 28;65(Pt 4):o919. doi: 10.1107/S1600536809010873

(Z)-2-Amino-3-[(E)-benzylideneamino]but-2-enedinitrile

G Varsha ^a, V Arun ^a, Manju Sebastian ^a, P Leeju ^a, Digna Varghese ^a, K K M Yusuff ^a,^*

PMCID: PMC2968917 PMID: 21582621

Abstract

The asymmetric unit of the title compound, C₁₁H₈N₄, contains two independent molecules. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link molecules into ribbons extended in the [100] direction.

Related literature

For some properties of Schiff base ligands, see: Arun, Robinson et al. (2009 ▶); Arun, Sridevi et al. (2009 ▶). For related structures, see: MacLachlan et al. (1996 ▶); Mague & Eduok (2000 ▶); Varghese et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₈N₄
M _r = 196.21
Monoclinic,
a = 6.9569 (19) Å
b = 22.796 (6) Å
c = 13.516 (4) Å
β = 100.983 (5)°
V = 2104.2 (10) Å³
Z = 8
Mo Kα radiation radiation
μ = 0.08 mm⁻¹
T = 298 K
0.42 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.980, T _max = 0.984
12239 measured reflections
4173 independent reflections
3216 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.106
wR(F ²) = 0.214
S = 1.29
4173 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010873/cv2533sup1.cif

e-65-0o919-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010873/cv2533Isup2.hkl

e-65-0o919-Isup2.hkl^{(200.4KB, 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
N2—H2A⋯N3ⁱ	0.86	2.36	3.096 (4)	144
N2—H2B⋯N8ⁱⁱ	0.86	2.25	3.090 (5)	165
N6—H6A⋯N7ⁱⁱⁱ	0.86	2.51	3.228 (5)	142
N6—H6B⋯N4^iv	0.86	2.28	3.057 (4)	150

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

Acknowledgments

The X-ray data were collected on the diffractometer facilities at the University of Hyderabad provided by the Department of Science and Technology. MS thanks KSCSTE, Trivandrum, Kerala, for financial assistance. DV gratefully acknowledges financial support from the Council of Scientific and Industrial Research (CSIR), India.

supplementary crystallographic information

Comment

In continuation of our study of Schiff base ligands and their metal complexes (Arun, Robinson et al., 2009; Arun, Sridevi et al., 2009; Varghese et al., 2009), we present here the title compound, (I).

The asymmetric unit of (I) contains two independent molecules (Fig. 1). All bond lengths and angles in (I) are normal and correspond to those observed in the related compounds (MacLachlan et al., 1996; Mague & Eduok 2000). In both independent molecules, the benzene ring and diaminomaleonitrile moiety are anti with respect to azomethine C=N. In the crystal structure, intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into ribbons extended in direction [100].

Experimental

Benzaldehyde (Merck) and 2,3-diaminomaleonitrile (Aldrich) are of reagent grade and are used without further purification. A hot solution of 2,3-diaminomaleonitrile (1 mmol) in methanol (25 ml) was added slowly over a hot solution of benzaldehyde (1 mmol) in the same solvent (25 ml) and the solution was refluxed for three hours. The resulting yellow solution was cooled in ice and the precipitated imine was filtered off and washed with cold methanol and dried under vacuum. Yellow crystals of (1) suitable for X-ray analysis were obtained by slow evaporation of the Schiff base in absolute ethanol (yield 85%; m.p. 463 K).