2-Formyl-6-meth­oxy­phenyl cinnamate

N Manikandan; S Murugavel; D Kannan; M Bakthadoss

doi:10.1107/S160053681202747X

. 2012 Jun 23;68(Pt 7):o2167. doi: 10.1107/S160053681202747X

2-Formyl-6-methoxyphenyl cinnamate

N Manikandan ^a, S Murugavel ^b,^*, D Kannan ^c, M Bakthadoss ^c,^‡

PMCID: PMC3393973 PMID: 22798838

Abstract

In the title compound, C₁₇H₁₄O₄, the C=C bond adopts an E conformation and the dihedral angle between the benzene rings is 73.9 (1)°. The crystal packing features C—H⋯O hydrogen bonds, which generate C(4) chains propagating along the b-axis direction. Weak aromatic π–π stacking interactions [centroid–centroid distance = 3.703 (1) Å] are also observed.

Related literature

For the biological properties of cinnamate derivatives, see: Sharma (2011 ▶). For related structures, see: Kaitner & Stilinović (2007 ▶); Anuradha et al. (2012 ▶).

Experimental

Crystal data

C₁₇H₁₄O₄
M _r = 282.28
Orthorhombic,
a = 10.7908 (7) Å
b = 10.4672 (5) Å
c = 25.8714 (17) Å
V = 2922.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.910, T _max = 0.941
14344 measured reflections
2665 independent reflections
1909 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.106
S = 1.01
2665 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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/S160053681202747X/hb6858sup1.cif

e-68-o2167-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202747X/hb6858Isup2.hkl

e-68-o2167-Isup2.hkl^{(128.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202747X/hb6858Isup3.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
C9—H9⋯O3ⁱ	0.93	2.50	3.415 (2)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Cinnamic acid and its derivatives including esters and carboxylic functional derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. They are used as cosmetic grades and as sunscreen agents to reduce skin damage by blocking UV—A, B (Sharma, 2011). As part of our studies in this area, the crystal structure determination of the title compound was carried out and the results are presented here.

The C9=C10 double bond of the title compound (I) exists in an E-configuration (Fig. 1). The dihedral angle between the two benzene rings is 73.9 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Kaitner et al., 2007, Anuradha et al., 2012).

The crystal packing features C—H···O hydrogen bonds. Atom C9 at x, y, z donates one proton to atom O3 at 3/2 - x, 1/2 + y, z, forming C(4) chains along the b axis (Fig. 2). The crystal packing (Fig. 3) also features π—π interactions with a Cg—Cg^iv seperation of 3.703 (1) Å.[Fig. 3; Cg is the centroid of the C1–C6 benzene ring, symmetry code as in Fig. 3].

Experimental

To a stirred solution of 2-hydroxy-3-methoxybenzaldehyde (1 mmol, 0.154 g) and potassium carbonate (1.5 mmol, 0.207 g) was stirred for 15 minutes in acetonitrile as solvent at room temperature. To this solution, (2E)-3-phenylprop-2-enoylchloride (1 mmol, 0.167 g) was added till the addition is complete. After the completion of the reaction as indicated by TLC, acetonitrile solvent was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product. The pure title compound was obtained as a colorless solid (0.250 g, 89% yield). Recrystallization was carried out using ethylacetate as solvent to yield colourless blocks.