3-(m-Tol­yloxy)phthalonitrile

Zhang, X.-F.; Jia, D.; Liu, Q.; Song, A.

doi:10.1107/S1600536807068225

Volume 64
Part 2
Page o401
February 2008

Received 1 December 2007
Accepted 22 December 2007
Online 9 January 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.110
Data-to-parameter ratio = 13.7
Details

3-(m-Tolyloxy)phthalonitrile

Xian-Fu Zhang,^a ^* Dandan Jia,^a Qiang Liu ^b and Aijun Song ^a

^aDepartment of Chemistry, Hebei Normal University of Science and Technology, Qinhuangdao, Hebei Province 066004, People's Republic of China, and ^bDepartment of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China
Correspondence e-mail: zhangxianfu@tsinghua.org.cn

In the molecule of the title compound, C₁₅H₁₀N₂O, the dihedral angle between the two benzene rings is 65.49 (9)°.

Related literature

For the synthesis of a related compound, see: Sharman & van Lier (2003). For the crystal structure of an isomer of the title compound see: Ocak Ískeleli (2007). For related literature, see: Atalay et al. (2003, 2004); Cave et al. (1986); Koysal et al. (2004); Leznoff & Lever (1989-1996); McKeown (1998); Ocak et al. (2003).

Experimental

Crystal data

C₁₅H₁₀N₂O
M_r = 234.25
Orthorhombic, P b c a
a = 25.514 (3) Å
b = 14.6064 (18) Å
c = 6.6109 (6) Å
V = 2463.7 (5) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 295 (2) K
0.6 × 0.5 × 0.3 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
3094 measured reflections
2254 independent reflections
1372 reflections with I > 2(I)
R_int = 0.041
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.109
S = 1.04
2254 reflections
165 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.23 e Å^-3

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2070 ).

Acknowledgements

The authors thank the HBUST for financial support.

References

Atalay, S., Agar, A., Akdemir, N. & Agar, E. (2003). Acta Cryst. E59, o1111-o1112.
Atalay, S., Çoruh, U., Akdemir, N. & Agar, E. (2004). Acta Cryst. E60, o303-o305.
Bruker. (1997). SHELXTL and XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cave, R. J., Siders, P. & Marcus, R. A. (1986). J. Phys. Chem. 90, 1436-1439.
Köysal, Y., Isik, S., Akdemir, N., Agar, E. & Kantar, C. (2004). Acta Cryst. E60, o930-o931.
Leznoff, C. C. & Lever, A. B. P. (1989-1996). Phthalocyanines: Properties and Applications , Vol. 1. pp. 1-20. Weinheim/New York: VCH Publishers Inc.
McKeown, N. B. (1998). Phthalocyanine Materials: Synthesis, Structure and Function. pp. 12-30. Cambridge University Press.
Ocak Ískeleli, N. (2007). Acta Cryst. E63, o997-o998.
Ocak, N., Agar, A., Akdemir, N., Agar, E., García-Granda, S. & Erdönmez, A. (2003). Acta Cryst. E59, o1000-o1001.
Sharman, W. M. & van Lier, J. E. (2003). The Porphyrin Handbook, Vol. 15, edited by K. M. Kadish, K. M. Smith & G. Guilard, pp. 1-60. New York: Academic Press.

organic compounds