4-(4-Cyano­benzoyl­meth­yl)benzonitrile

Wang, W.; Zhao, H.

doi:10.1107/S1600536808015079

Volume 64
Part 6
Page o1148
June 2008

Received 1 May 2008
Accepted 19 May 2008
Online 24 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.060
wR = 0.157
Data-to-parameter ratio = 16.8
Details

4-(4-Cyanobenzoylmethyl)benzonitrile

Wenxiang Wang ^a and Hong Zhao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: zhaohong@seu.edu.cn

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-HN and C-HO hydrogen-bond interactions, forming chains running parallel to the b axis.

Related literature

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

Experimental

Crystal data

C₁₆H₁₀N₂O
M_r = 246.26
Triclinic, $[P \overline 1]$
a = 7.5217 (15) Å
b = 7.9759 (16) Å
c = 10.881 (2) Å
= 96.78 (3)°
= 93.34 (3)°
= 102.10 (3)°
V = 631.5 (2) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.157
S = 1.04
2898 reflections
173 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1ⁱ	0.93	2.62	3.486 (3)	154
C12-H12O1ⁱⁱ	0.93	2.42	3.268 (2)	152
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2215 ).

Acknowledgements

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

References

Arici, C., Ülkü, D., Kirilmis, C., Koca, M. & Ahmedzade, M. (2004). Acta Cryst. E60, o1211-o1212.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Radl, S., Hezky, P., Konvicka, P. & Krejgi, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhao, Y.-Y. (2008). Acta Cryst. E64, o761.

organic compounds