(2,6-Diisopropyl­phen­yl)(2-thienylmethyl­ene)amine

Imhof, W.

doi:10.1107/S1600536809006291

Volume 65
Part 3
Page o593
March 2009

Received 19 February 2009
Accepted 20 February 2009
Online 25 February 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R = 0.028
wR = 0.079
Data-to-parameter ratio = 5.9
Details

(2,6-Diisopropylphenyl)(2-thienylmethylene)amine

Wolfgang Imhof ^a ^*

^aInstitute of Inorganic and Analytical Chemistry, Friedrich Schiller University, August-Bebel-Strasse 2, 07743 Jena, Germany
Correspondence e-mail: wolfgang.imhof@uni-jena.de

The title compound, C₁₇H₂₁NS, was prepared by the condensation of thiophene-2-carbaldehyde with 2,6-diisopropylaniline. It crystallizes with two molecules in the asymmetric unit. The molecules are interconnected via a C-HN hydrogen bond. The dihedral angles between the thiophene and phenyl rings are 81.7 (7) and 85.5 (7)°.

Related literature

For the synthetic procedure, see: Drisko & McKennis (1952); Wang et al. (2007). For related structures, see: Kazak et al. (2000); Maleki et al. (2007). For the organometallic chemistry of related ligands, see: Imhof (1997a,b).

Experimental

Crystal data

C₁₇H₂₁NS
M_r = 271.42
Monoclinic, P 2₁
a = 10.0877 (9) Å
b = 14.275 (3) Å
c = 11.4503 (9) Å
= 109.651 (8)°
V = 1552.8 (4) Å³
Z = 4
Mo K radiation
= 0.20 mm^-1
T = 173 K
0.51 × 0.43 × 0.33 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.884, T_max = 0.939
2222 measured reflections
2096 independent reflections
2055 reflections with I > 2(I)
R_int = 0.023
_max = 23.0°
3 standard reflections frequency: 120 min intensity decay: 0.02%

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.079
S = 1.08
2096 reflections
353 parameters
1 restraint
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C20-H20N1	0.93	2.52	3.449 (8)	178

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: SET4 (de Boer et al., 1984); data reduction: MolEN (Enraf-Nonius, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2882 ).

Acknowledgements

The author thanks the Deutsche Forschungsgemeinschaft (SFB 436) for financial support.

References

Boer, J. L. de & Duisenberg, A. J. M. (1984). Acta Cryst. A40, C410.
Drisko, R. W. & McKennis, H. Jr (1952). J. Am. Chem. Soc. 74, 2626-2628.
Enraf-Nonius (1990). MolEN. Enraf-Nonius BV, Delft, The Netherlands.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Imhof, W. (1997a). J. Organomet. Chem. 533, 31-43.
Imhof, W. (1997b). J. Organomet. Chem. 541, 109-116.
Kazak, C., Aygün, M., Turgut, G., Odabasoglu, M., Özbey, S. & Büyükgüngör, O. (2000). Acta Cryst. C56, 1044-1045.
Malecki, J. G., Kruszynski, R. & Jarosz, G. (2007). Acta Cryst. E63, o3368-o3369.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1990). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wang, D., Cui, D., Miao, W., Li, S. & Huang, B. (2007). Dalton Trans. pp. 4576-4581.

organic compounds