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Volume 68 
Part 12 
Page o3326  
December 2012  

Received 24 September 2012
Accepted 6 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.149
Data-to-parameter ratio = 14.4
Details
Open access

2-Methyl-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

There are two independent molecules in the asymmetric unit of the title compound, C13H14N2, in which the dihedral angles formed by the pyrrole and benzene rings are 83.63 (8) and 87.84 (8)°. In the crystal, molecules are linked via pairs of N-H...N hydrogen bonds, forming inversion dimers, which are further connected by C-H...[pi] interactions.

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.]); Kazushi & Hayato (2005[Kazushi, M. & Hayato, T. (2005). J. Organomet. Chem. 690, 4414-4423.]). For pyrrole monoimine, 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
  • C13H14N2

  • Mr = 198.26

  • Triclinic, [P \overline 1]

  • a = 10.120 (2) Å

  • b = 10.400 (3) Å

  • c = 11.726 (3) Å

  • [alpha] = 79.138 (4)°

  • [beta] = 67.021 (4)°

  • [gamma] = 88.154 (4)°

  • V = 1114.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.38 × 0.29 × 0.17 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 = 0.973, Tmax = 0.988

  • 5729 measured reflections

  • 3981 independent reflections

  • 2530 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.149

  • S = 1.03

  • 3981 reflections

  • 276 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7-C12 and C20-C25 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.27 3.070 (3) 154
N3-H3...N4ii 0.86 2.30 3.108 (2) 156
C1-H1A...Cg1iii 0.93 2.70 3.488 (4) 143
C14-H14...Cg2iv 0.93 2.75 3.531 (3) 142
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+1, -z+2; (iii) -x+1, -y, -z; (iv) -x, -y+1, -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: LX2269 ).


Acknowledgements

This work was supported by the Natural Science Basic Research Plan in Shaanxi Province (Nos. 2009JQ2006 and 2010JQ2003) 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]
Kazushi, M. & Hayato, T. (2005). J. Organomet. Chem. 690, 4414-4423.
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]


Acta Cryst (2012). E68, o3326  [ doi:10.1107/S1600536812045849 ]

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