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

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

doi:10.1107/S1600536812040858

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.156
Data-to-parameter ratio = 16.4
Details

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

Bi-Yun Su,^a ^* Wen-Long Qin ^b 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

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-HN 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); Dawson et al. (2000); Wu et al. (2003). For the pyrrole diimine unit, see: Matsuo et al. (2001) and for the pyrrole monoimine unit, see: He et al. (2009); Su et al. (2009a,b).

Experimental

Crystal data

C₁₄H₁₆N₂
M_r = 212.29
Monoclinic, P 2₁ /n
a = 12.5894 (17) Å
b = 7.3109 (10) Å
c = 14.8425 (19) Å
= 113.118 (2)°
V = 1256.4 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.976, T_max = 0.990
6463 measured reflections
2441 independent reflections
1885 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.156
S = 0.96
2441 reflections
149 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1N2ⁱ	0.86	2.34	3.1354 (18)	155
C1-H1ACg1ⁱ	0.93	2.65	3.4298 (16)	142
Symmetry code: (i) -x, -y+2, -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: 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.
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.
Matsuo, Y., Mashima, K. & Tani, K. (2001). Organometallics, 20, 3510-3518.
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.
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.

organic compounds