Diethyl 2-[(1-methyl-1H-pyrrol-2-yl)methyl­ene­amino]-5-(2-thienylmethyl­ene­amino)thio­phene-3,4-dicarboxyl­ate

Dufresne, S.; Skene, W.G.

doi:10.1107/S160053680800799X

Volume 64
Part 5
Page o782
May 2008

Received 5 March 2008
Accepted 25 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.115
Data-to-parameter ratio = 10.3
Details

Diethyl 2-[(1-methyl-1H-pyrrol-2-yl)methyleneamino]-5-(2-thienylmethyleneamino)thiophene-3,4-dicarboxylate

Stéphane Dufresne ^a and W. G. Skene ^a ^*

^aDepartment of Chemistry, University of Montreal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7
Correspondence e-mail: w.skene@umontreal.ca

Both imine bonds of the title compound, C₂₁H₂₁N₃O₄S₂, were found to be in the E configuration. The terminal pyrrole and thiophene rings are twisted by 2.5 (3) and 2.3 (2)°, respectively, from the mean plane of the central thiophene to which they are attached. The structure is disordered by exchange of the terminal heterocyclic rings; the site occupancy factors are ca 0.8 and 0.2. The crystal packing involves some [pi] - [pi] stacking [3.449 (4) Å between pyrrole and terminal thiophene rings].

Related literature

For general background, see: Dufresne et al. (2007). For a similar compound, see: Dufresne et al. (2006).

Experimental

Crystal data

C₂₁H₂₁N₃O₄S₂
M_r = 443.53
Monoclinic, C 2/c
a = 30.7355 (14) Å
b = 6.9617 (4) Å
c = 19.5163 (9) Å
= 92.732 (2)°
V = 4171.2 (4) Å³
Z = 8
Cu K radiation
= 2.60 mm^-1
T = 150 (2) K
0.14 × 0.09 × 0.05 mm

Data collection

Bruker SMART 6K diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.712, T_max = 0.881
24275 measured reflections
4076 independent reflections
3330 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.115
S = 1.03
4076 reflections
394 parameters
544 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.38 e Å^-3

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: UdMX (Marris, 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2192 ).

Acknowledgements

The authors acknowledge financial support from the Natural Sciences and Engineering Research Council Canada, the Centre for Self-Assembled Chemical Structures, and Canada Foundation for Innovation. SD thanks the Université de Montréal for a graduate scholarship.

References

Bruker (2003). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dufresne, S., Bourgeaux, M. & Skene, W. G. (2006). Acta Cryst. E62, o5602-o5604.
Dufresne, S., Bourgeaux, M. & Skene, W. G. (2007). J. Mater. Chem. 17, 1166-1177.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Marris, T. (2004). UdMX. Université de Montréal, Montréal, Québec, Canada.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds