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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 [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.127
Data-to-parameter ratio = 18.7
Details
Open access

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

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-H...N 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[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.]); Crestani et al. (2011[Crestani, M. G., Manbeck, G. F., Brennessel, W. W., McCormick, T. M. & Eisenberg, R. (2011). Inorg. Chem. 50, 7172-7188.]); Matsui et al. (2004[Matsui, S., Yoshida, Y., Takagi, Y., Spaniol, T. P. & Okuda, J. (2004). J. Organomet. Chem. 689, 1155-1164.]); Wang et al. (2007[Wang, Y., Fu, H., Peng, A., Zhao, Y., Ma, J. & Yao, J. (2007). Chem. Commun. pp. 1623-1625.]); Franceschi et al. (2001[Franceschi, F., Guillemont, G., Solari, E., Floriani, C., Re, N., Birkedal, H. & Pattison, P. (2001). Chem. Eur. J. 7, 1468-1478.]); Tahir et al. (2010[Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Tariq, R. H. (2010). Acta Cryst. E66, o2295.]); Munro et al. (2006[Munro, O. Q., Joubert, S. D. & Grimmer, C. D. (2006). Chem. Eur. J. 12, 7987-7999.]). For standard bond lengths, see: Allen et al. (1987[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.]). For graph-set description, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573. ]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2

  • Mr = 212.29

  • Monoclinic, P 21 /c

  • a = 13.6739 (10) Å

  • b = 7.3086 (6) Å

  • c = 13.3880 (11) Å

  • [beta] = 111.184 (4)°

  • V = 1247.54 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 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[Nonius (1998). COLLECT, Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[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.]); data reduction: DENZO; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: 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.   [CrossRef] [ChemPort] [ISI]
Crestani, M. G., Manbeck, G. F., Brennessel, W. W., McCormick, T. M. & Eisenberg, R. (2011). Inorg. Chem. 50, 7172-7188.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Franceschi, F., Guillemont, G., Solari, E., Floriani, C., Re, N., Birkedal, H. & Pattison, P. (2001). Chem. Eur. J. 7, 1468-1478.  [CSD] [CrossRef] [PubMed] [ChemPort]
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.  [CSD] [CrossRef] [ChemPort] [PubMed]
Matsui, S., Yoshida, Y., Takagi, Y., Spaniol, T. P. & Okuda, J. (2004). J. Organomet. Chem. 689, 1155-1164.  [CSD] [CrossRef] [ChemPort]
Munro, O. Q., Joubert, S. D. & Grimmer, C. D. (2006). Chem. Eur. J. 12, 7987-7999.  [CSD] [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [details]
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Tariq, R. H. (2010). Acta Cryst. E66, o2295.  [CSD] [CrossRef] [details]
Wang, Y., Fu, H., Peng, A., Zhao, Y., Ma, J. & Yao, J. (2007). Chem. Commun. pp. 1623-1625.  [CSD] [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o113  [ doi:10.1107/S160053681205057X ]

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