4-(4-Cyano­benzoyl­meth­yl)benzonitrile

Wenxiang Wang; Hong Zhao

doi:10.1107/S1600536808015079

. 2008 May 24;64(Pt 6):o1148. doi: 10.1107/S1600536808015079

4-(4-Cyanobenzoylmethyl)benzonitrile

Wenxiang Wang ^a, Hong Zhao ^a,^*

PMCID: PMC2961399 PMID: 21202656

Abstract

In the title compound, C₁₆H₁₀N₂O, the dihedral angle formed by the benzene rings is 84.99 (7)°. The crystal structure is stabilized by intermolecular C—H⋯N and C—H⋯O hydrogen-bond interactions, forming chains running parallel to the b axis.

Related literature

For related literature, see: Arıcı et al. (2004 ▶); Radl et al. (2000 ▶); Bernstein et al. (1995 ▶); Zhao (2008 ▶).

Experimental

Crystal data

C₁₆H₁₀N₂O
M _r = 246.26
Triclinic,
a = 7.5217 (15) Å
b = 7.9759 (16) Å
c = 10.881 (2) Å
α = 96.78 (3)°
β = 93.34 (3)°
γ = 102.10 (3)°
V = 631.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.16 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.964, T _max = 0.988
6576 measured reflections
2898 independent reflections
1943 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.157
S = 1.04
2898 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks I, global. DOI: 10.1107/S1600536808015079/rz2215sup1.cif

e-64-o1148-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015079/rz2215Isup2.hkl

e-64-o1148-Isup2.hkl^{(142.2KB, 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
C3—H3⋯N1ⁱ	0.93	2.62	3.486 (3)	154
C12—H12⋯O1ⁱⁱ	0.93	2.42	3.268 (2)	152

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

Acknowledgments

This work was supported by a Start-up Grant from SEU to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Benzonitriles and their derivatives are important starting materials in the synthesis of some heterocyclic molecules (Radl et al., 2000; Arıcı et al., 2004). As part of our ongoing study on benzonitrile derivatives (Zhao, 2008), the crystal structure of one such derivatives is reported here.

The molecular structure of the title compound (Fig. 1) shows normal bond lengths and angles. The C≡N triple bond and C=O double bond lengths are 1.142 (2) and and 1.193 (2) Å, respectively. The benzene ring are oriented nearly perpendicular to each other, the dihedral angle they form being 84.99 (7)°. In the crystal structure, centrosymmetrically-related molecules are linked into dimeric units by intermolecular C—H···N hydrogen bonds (Table 1) forming ten-membered rings of graph-set R²₂(10) (Berstein et al., 1995). These dimers are further connected by intermolecular C—H···O hydrogen interactions to form chains running parallel to the b axis.

Experimental

To a solution of sodium cyanide (2 g) in water (18 ml) was added 4-formylbenzonitrile (2.62 g). The mixture was stirred for 15 min at room temperature, then a saturated sodium hydrosulfite solution (15 ml) was added dropwise. The resulting mixture was stirred at 293K until a yellow solid was obtained. The solid was filtered and recrystallized from a mixture of methanol (18 ml) and DMF (6 ml), to give crystals of the title compound suitable for X-ray diffraction analysis on slow evaporation of the solvents.