2-[2-(4-Meth­oxy­phen­yl)-2-oxoeth­yl]malononitrile

Mi Lian; Tianli Chen; Yanping Zhu

doi:10.1107/S1600536811026961

. 2011 Jul 13;67(Pt 8):o2007. doi: 10.1107/S1600536811026961

2-[2-(4-Methoxyphenyl)-2-oxoethyl]malononitrile

Mi Lian ^a,^*, Tianli Chen ^b, Yanping Zhu ^a

PMCID: PMC3213462 PMID: 22091041

Abstract

The title compound, C₁₂H₁₀N₂O₂, was obtained unintentionally during the synthesis of 2-amino-5-(4-methoxyphenyl)furan-3-carbonitrile. In the crystal, weak intermolecular C—H⋯N and C—H⋯π interactions link the molecules into columns propagating in [010].

Related literature

For the crystal structures of related compounds with a malononitrile fragment, see: Luo & Zhou (2006 ▶); Ohashi et al. (2008 ▶); Oliva et al. (2010 ▶).

Experimental

Crystal data

C₁₂H₁₀N₂O₂
M _r = 214.22
Monoclinic,
a = 11.9010 (13) Å
b = 6.4898 (7) Å
c = 14.4248 (16) Å
β = 100.141 (2)°
V = 1096.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
11044 measured reflections
2148 independent reflections
1693 reflections with I > 2σ(I)
R _int = 0.123

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.137
S = 1.07
2148 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026961/cv5094sup1.cif

e-67-o2007-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026961/cv5094Isup2.hkl

e-67-o2007-Isup2.hkl^{(105.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026961/cv5094Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯N1ⁱ	0.97	2.55	3.380 (2)	143
C10—H10⋯Cgⁱⁱ	0.98	2.56	3.411 (1)	145

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

Acknowledgments

The authors are grateful to the Central China Normal University for financial support and thank Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

The title compound (I) has been unintentionally obtained in the process of synthesis of 2-amino-5-(4-methoxyphenyl)furan-3-carbonitrile.

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those observed in related compounds (Luo & Zhou, 2006; Ohashi et al., 2008; Oliva et al., 2010). In the crystal structure, weak intermolecular C—H···N and C—H···π interactions (Table 1) link the molecules into columns propagated in [010].

Experimental

To a solution of K₂CO₃ (2.0 equiv) in MeOH,3-iodo-1-(4-methoxyphenyl)propan-1-one (1.0 equiv) and malononitrile (2.0 equiv) were separately added. The resulting mixture was then heated at reflux for several hours (TLC monitoring). After that, the solvent was removed under reduce pressure, and added 50 mL water to the residue, then extracted with EtOAc 3 times. The organic phase was washed with saturated saline solution. Then the organic phase was dried by anhydrous Na2SO4, and removed the EtOAc under reduce pressure. The final residue was purified by column chromatography on silica gel to afford the expected target compound as a white solid.