[Journal logo]

Volume 69 
Part 12 
Page o1808  
December 2013  

Received 23 October 2013
Accepted 15 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 16.1
Details
Open access

2,5-Di­meth­oxy­benzo­nitrile

aFachbereich Chemie, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany,bDepartment of Chemical Engineering, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates, and cDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates
Correspondence e-mail: thies@uaeu.ac.ae

In the title mol­ecule, C9H9NO2, the non-H atoms are essentially coplanar with a maximum deviation of 0.027 (2) Å for the C atom of one of the methyl groups. In the crystal, the mol­ecules are arranged into centrosymmetric pairs via pairs of C-H...O and C-H...N inter­actions whereas [pi]-[pi] stacking inter­actions between the benzene rings [centroid-centroid distance 3.91001 (15) Å] organize them into polymeric strands propagating along the a-axis direction. There is a step of 0.644 (2) Å between the two planar parts of the centrosymmetric pair. In neighboring strands related by the n-glide operation, the aromatic rings are tilted by 29.08 (2)°.

Related literature

For the use of the title compound as a key reagent in the synthesis of pharmaceutically active heterocycles, see: Bergeron et al. (2006[Bergeron, R. J., Wiegand, J., McManis, J. S. & Bharti, N. (2006). J. Med. Chem. 49, 7032-7043.]); Delgado et al. (1987[Delgado, A., Mauleon, D., Rosell, G., Salas, M. L. & Najar, J. (1987). Anal. Quim. Ser. C, 83, 90-95.]). For another method of preparation of the title compound, see: Ushijima et al. (2012[Ushijima, S., Moriyama, K. & Togo, H. (2012). Tetrahedron, 68, 4588-4595.]). For the crystal structures of aromatic nitriles, see: Buschmann et al. (1995[Buschmann, W. E., Arif, A. M. & Miller, J. S. (1995). J. Chem. Soc. Chem. Commun. pp. 2343-2344.]); Zabinski et al. (2007[Zabinski, J., Wolska, I. & Maciejewska, D. (2007). J. Mol. Struct. 833, 74-81.]); Zanotti et al. (1980[Zanotti, G., Bardi, R. & Del Pra, A. (1980). Acta Cryst. B36, 168-171.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9NO2

  • Mr = 163.17

  • Monoclinic, P 21 /n

  • a = 3.91001 (15) Å

  • b = 11.3347 (4) Å

  • c = 17.8432 (6) Å

  • [beta] = 93.400 (3)°

  • V = 789.40 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.60 × 0.25 × 0.23 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.899, Tmax = 1.000

  • 3225 measured reflections

  • 1785 independent reflections

  • 1374 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.06

  • 1785 reflections

  • 111 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8B...O1i 0.98 2.65 3.428 (2) 136
C8-H8B...N1i 0.98 2.73 3.504 (2) 136
C9-H9B...N1ii 0.98 2.71 3.640 (2) 158
Symmetry codes: (i) -x+3, -y+2, -z+1; (ii) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2594 ).


References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bergeron, R. J., Wiegand, J., McManis, J. S. & Bharti, N. (2006). J. Med. Chem. 49, 7032-7043.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Buschmann, W. E., Arif, A. M. & Miller, J. S. (1995). J. Chem. Soc. Chem. Commun. pp. 2343-2344.  [CrossRef] [Web of Science]
Delgado, A., Mauleon, D., Rosell, G., Salas, M. L. & Najar, J. (1987). Anal. Quim. Ser. C, 83, 90-95.  [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ushijima, S., Moriyama, K. & Togo, H. (2012). Tetrahedron, 68, 4588-4595.  [Web of Science] [CrossRef] [ChemPort]
Zabinski, J., Wolska, I. & Maciejewska, D. (2007). J. Mol. Struct. 833, 74-81.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zanotti, G., Bardi, R. & Del Pra, A. (1980). Acta Cryst. B36, 168-171.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1808  [ doi:10.1107/S1600536813031309 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.