(E)-2,4,6-Trimethyl-N-[(1H-pyrrol-2-yl)methyl­idene]aniline

Imhof, W.

doi:10.1107/S160053681205057X

Volume 69
Part 1
Page o113
January 2013

Received 27 November 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.127
Data-to-parameter ratio = 18.7
Details

(E)-2,4,6-Trimethyl-N-[(1H-pyrrol-2-yl)methylidene]aniline

Wolfgang Imhof ^a ^*

^aUniversity Koblenz-Landau, Institute for Integrated Natural Sciences, Universitätsstrasse 1, 56070 Koblenz, Germany
Correspondence e-mail: Imhof@uni-koblenz.de

The title compound, C₁₄H₁₆N₂, is a pyrrole-2-carbaldimine ligand that shows an E conformation at the imine double bond. The dihedral angle between the rings is 78.3 (1)°. In the crystal, pairs of molecules form centrosymmetric dimers [graph-set descriptor is presumably R²₂(10)] via N-HN hydrogen bonds between the pyrrole N-H group and the imine N atom of a neighbouring molecule.

Related literature

For structure analyses of other pyrrole-2-carbaldimines in which the substituents at the imine N atoms do not include functional groups that are capable of forming additional hydrogen bonds, see: Gomes et al. (2010); Crestani et al. (2011); Matsui et al. (2004); Wang et al. (2007); Franceschi et al. (2001); Tahir et al. (2010); Munro et al. (2006). For standard bond lengths, see: Allen et al. (1987). For graph-set description, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₆N₂
M_r = 212.29
Monoclinic, P 2₁ /c
a = 13.6739 (10) Å
b = 7.3086 (6) Å
c = 13.3880 (11) Å
= 111.184 (4)°
V = 1247.54 (17) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 183 K
0.6 × 0.4 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer
4714 measured reflections
2849 independent reflections
1346 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.127
S = 0.87
2849 reflections
152 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.94 (2)	2.05 (2)	2.909 (2)	150.7 (17)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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: BT6872 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Crestani, M. G., Manbeck, G. F., Brennessel, W. W., McCormick, T. M. & Eisenberg, R. (2011). Inorg. Chem. 50, 7172-7188.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Franceschi, F., Guillemont, G., Solari, E., Floriani, C., Re, N., Birkedal, H. & Pattison, P. (2001). Chem. Eur. J. 7, 1468-1478.
Gomes, C. S. B., Suresh, D., Gomes, P. T., Veiros, L. F., Duarte, M. T., Nunes, T. G. & Oliveira, M. C. (2010). Dalton Trans. 39, 736-748.
Matsui, S., Yoshida, Y., Takagi, Y., Spaniol, T. P. & Okuda, J. (2004). J. Organomet. Chem. 689, 1155-1164.
Munro, O. Q., Joubert, S. D. & Grimmer, C. D. (2006). Chem. Eur. J. 12, 7987-7999.
Nonius (1998). COLLECT, Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Tariq, R. H. (2010). Acta Cryst. E66, o2295.
Wang, Y., Fu, H., Peng, A., Zhao, Y., Ma, J. & Yao, J. (2007). Chem. Commun. pp. 1623-1625.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds