2-Methyl-N-[1-(1H-pyrrol-2-yl)ethyl­idene]aniline

Su, B.; Qin, W.-L.; Jiao, L.; Wang, J.-X.

doi:10.1107/S1600536812045849

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 (C-C) = 0.003 Å
R = 0.051
wR = 0.149
Data-to-parameter ratio = 14.4
Details

2-Methyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline

Bi-yun Su,^a ^* Wen-Long Qin,^b Long Jiao ^a and Jia-Xiang Wang ^a

^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-HN 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); Dawson et al. (2000); Kazushi & Hayato (2005). For pyrrole monoimine, see: He et al. (2009); Su et al. (2009a,b).

Experimental

Crystal data

C₁₃H₁₄N₂
M_r = 198.26
Triclinic, $[P \overline 1]$
a = 10.120 (2) Å
b = 10.400 (3) Å
c = 11.726 (3) Å
= 79.138 (4)°
= 67.021 (4)°
= 88.154 (4)°
V = 1114.7 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.973, T_max = 0.988
5729 measured reflections
3981 independent reflections
2530 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.149
S = 1.03
3981 reflections
276 parameters
2 restraints
H-atom parameters constrained
_max = 0.19 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N1-H1N2ⁱ	0.86	2.27	3.070 (3)	154
N3-H3N4ⁱⁱ	0.86	2.30	3.108 (2)	156
C1-H1ACg1ⁱⁱⁱ	0.93	2.70	3.488 (4)	143
C14-H14Cg2^iv	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); cell refinement: SAINT (Bruker,2008); data reduction: SAINT; 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: publCIF (Westrip, 2010).

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.
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.
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.
Kazushi, M. & Hayato, T. (2005). J. Organomet. Chem. 690, 4414-4423.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009a). Synth. Commun. 39, 4429-4440.
Su, B.-Y., Zhao, J.-S., Zhang, Q.-Z. & Qin, W.-L. (2009b). Polym. Int. 58, 1051-1057.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds