2-[(4-Formyl­phen­yl)(hy­droxy)meth­yl]acrylonitrile

C M Sai Prasanna; K Sethusankar; R Rajesh; R Raghunathan

doi:10.1107/S160053681102976X

. 2011 Jul 30;67(Pt 8):o2176. doi: 10.1107/S160053681102976X

2-[(4-Formylphenyl)(hydroxy)methyl]acrylonitrile

C M Sai Prasanna ^a, K Sethusankar ^b,^*, R Rajesh ^c, R Raghunathan ^c

PMCID: PMC3213610 PMID: 22091187

Abstract

In the title compound, C₁₁H₉NO₂, the mean planes formed by the phenyl and acryl group are almost orthogonal to each other, with a dihedral angle of 88.61 (7)°. The carbonitrile side chain is almost linear, the C—C—N angle being 179.54 (16)°. In the crystal, molecules are linked by intermolecular O—H⋯O interactions into infinite chains running parallel to the b axis.

Related literature

For uses of acrylonitrile derivatives, see: Ohsumi et al. (1998 ▶). For related structures, see: Cobo et al. (2005 ▶); Nizam Mohideen et al. (2007 ▶).

Experimental

Crystal data

C₁₁H₉NO₂
M _r = 187.19
Monoclinic,
a = 7.6089 (5) Å
b = 6.0895 (3) Å
c = 20.5135 (14) Å
β = 93.615 (2)°
V = 948.59 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
12108 measured reflections
2778 independent reflections
2109 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.137
S = 1.04
2778 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102976X/pv2428sup1.cif

e-67-o2176-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102976X/pv2428Isup2.hkl

e-67-o2176-Isup2.hkl^{(133.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102976X/pv2428Isup3.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
O2—H2⋯O1ⁱ	0.82	1.99	2.8107 (15)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

CMS and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.

supplementary crystallographic information

Comment

Acrylonitrile derivatives have been shown to possess antitubercular and antitumour activities (Ohsumi et al., 1998).

In the title compound (Fig. 1), the mean planes formed by the phenyl ring C2—C7 and acryl group (N1/C8—C11) are almost orthogonal to each other with a dihedral angle 88.61 (7)°. The bond length C9—C11 [1.4338 (18) Å] is significantly shorter than the expected value for a C—C single bond because of conjugation effects (Nizam Mohideen et al., 2007). The mean plane of C2—C1—O1 is slightly twisted out of the mean plane of phenyl ring C2—C7 with a dihedral angle 2.62 (9)°. The carbonitrile side chain (C9—C11—N1) is almost linear, with the angle around central carbon atom being 179.54 (16)°. The title compound exhibits structural similarities with closely related structures (Cobo et al.2005, Nizam Mohideen et al.2007).

In the title compound, the crystal packing is stabilized by O2—H2···O1 intermolecular interactions which link the molecules into infinite chains running parallel to the b-axis (Tab. 1 & Fig. 2).

Experimental

To a reaction mixture of terephthalaldehyde (1 mmol) and acrylonitrile (2 mmol) was added a catalytic quantity of 1,4-diazabicyclo[2.2.2]octane (10–15 mol %). The reaction mixture was left standing at room temperature in a stoppered sample flask. The progress of the reaction was monitored by Thin Layer Chromatography (TLC) over a period of several days. After 6 days the TLC revealed the presence of a product. The reaction mixture was dissolved in ethyl acetate and washed with aqueous HCl solution (0.25 M) and water followed by brine solution. The organic layer was separated and dried over sodium sulfate, filtering and evaporation of the organic solvent under reduced pressure. The product was seperated by flash column chromatography using hexane and ethyl acetate (4:1) as an eluent to give colorless solid. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for XRD studies.