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Volume 68 
Part 11 
Page o3088  
November 2012  

Received 21 September 2012
Accepted 27 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.156
Data-to-parameter ratio = 16.4
Details
Open access

2,5-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline

aCollege of Chemistry and Chemical Engineering, Xi'an ShiYou University, Xi'an, Shaanxi 710065, People's Republic of China, and bCollege of Petroleum Engineering, Xi'an ShiYou University, Xi'an, Shaanxi 710065, People's Republic of China
Correspondence e-mail: subiyun@xsyu.edu.cn

In the title compound, C14H16N2, the pyrrole and benzene rings form a dihedral angle of 72.37 (8)°. In the crystal, centrosymmetrically related molecules are assembled into dimers by by pairs of N-H...N hydrogen bonds, generating rings of R22(10) graph-set motif. C-H...[pi] interactions also occur.

Related literature

For general background to the iminopyrrole unit, see: Britovsek et al. (2003[Britovsek, G. J. P., Gibson, V. C., Hoarau, O. D., Spitzmesser, S. K., White, A. J. P. & Williams, D. J. (2003). Inorg. Chem. 42, 3454-3465.]); Dawson et al. (2000[Dawson, D. M., Walker, D. A., Thornton-Pett, M. & Bochmann, M. (2000). J. Chem. Soc. Dalton Trans. pp. 459-466.]); Wu et al. (2003[Wu, Z.-K., Chen, Q.-Q., Xiong, S.-X., Xin, B., Zhao, Z.-W., Jiang, L.-J. & Ma, J.-S. (2003). Angew. Chem. Int. Ed. 42, 3271-3274.]). For the pyrrole diimine unit, see: Matsuo et al. (2001[Matsuo, Y., Mashima, K. & Tani, K. (2001). Organometallics, 20, 3510-3518.]) and for the pyrrole monoimine unit, see: He et al. (2009[He, L.-P., Liu, J.-Y., Pan, L., Wu, J.-Q., Xu, B.-C. & Li, Y.-S. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 713-721.]); Su et al. (2009a[Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009a). Synth. Commun. 39, 4429-4440.],b[Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009b). Polym. Int. 58, 1051-1057.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2

  • Mr = 212.29

  • Monoclinic, P 21 /n

  • a = 12.5894 (17) Å

  • b = 7.3109 (10) Å

  • c = 14.8425 (19) Å

  • [beta] = 113.118 (2)°

  • V = 1256.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.37 × 0.28 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.990

  • 6463 measured reflections

  • 2441 independent reflections

  • 1885 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.156

  • S = 0.96

  • 2441 reflections

  • 149 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.34 3.1354 (18) 155
C1-H1A...Cg1i 0.93 2.65 3.4298 (16) 142
Symmetry code: (i) -x, -y+2, -z.

Data collection: APEX2 (Bruker,2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker,2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5010 ).


Acknowledgements

This work was supported by the Natural Science Basic Research Plan of Shaanxi Province (No. 2009JQ2006) and the Scientific Research Plan Project of Shaanxi Education Department (Nos. 12 J K0620 and 2010 J K784).

References

Britovsek, G. J. P., Gibson, V. C., Hoarau, O. D., Spitzmesser, S. K., White, A. J. P. & Williams, D. J. (2003). Inorg. Chem. 42, 3454-3465.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dawson, D. M., Walker, D. A., Thornton-Pett, M. & Bochmann, M. (2000). J. Chem. Soc. Dalton Trans. pp. 459-466.  [CSD] [CrossRef]
He, L.-P., Liu, J.-Y., Pan, L., Wu, J.-Q., Xu, B.-C. & Li, Y.-S. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 713-721.  [CrossRef] [ChemPort]
Matsuo, Y., Mashima, K. & Tani, K. (2001). Organometallics, 20, 3510-3518.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009a). Synth. Commun. 39, 4429-4440.  [ISI] [CrossRef] [ChemPort]
Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009b). Polym. Int. 58, 1051-1057.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wu, Z.-K., Chen, Q.-Q., Xiong, S.-X., Xin, B., Zhao, Z.-W., Jiang, L.-J. & Ma, J.-S. (2003). Angew. Chem. Int. Ed. 42, 3271-3274.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3088  [ doi:10.1107/S1600536812040858 ]

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