Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate

Wu, W.-N.; Wang, Y.; Wang, Q.-F.

doi:10.1107/S160053680902323X

Volume 65
Part 7
Page o1661
July 2009

Received 14 May 2009
Accepted 17 June 2009
Online 20 June 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.060
wR = 0.212
Data-to-parameter ratio = 18.7
Details

Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate

Wei-Na Wu,^a Yuan Wang ^a ^* and Qiu-Fen Wang ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
Correspondence e-mail: wangyuan08@hpu.edu.cn

The molecule of the title compound, C₁₀H₁₃NO₃, is approximately planar (maximum deviation 0.1424 Å). In the crystal, molecules are linked into inversion dimers by pairs of N-HO hydrogen bonds, and the dimeric units are linked by non-classical C-HO hydrogen bonds, forming a layered structure.

Related literature

For a related structure, see: Kang et al. (2008). For our studies of bis(pyrrol-2-yl-methyleneamine) ligands, see: Wang et al. (2008, 2009). For the synthesis, see: Wang et al. (2008).

Experimental

Crystal data

C₁₀H₁₃NO₃
M_r = 195.21
Triclinic, $[P \overline 1]$
a = 7.2223 (12) Å
b = 7.4347 (12) Å
c = 10.0488 (17) Å
= 78.412 (2)°
= 84.191 (2)°
= 79.051 (2)°
V = 517.84 (15) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.30 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.980, T_max = 0.986
6232 measured reflections
2416 independent reflections
1692 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.212
S = 1.07
2416 reflections
129 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.86	2.07	2.919 (2)	169
C5-H5AO1ⁱⁱ	0.93	2.54	3.347 (3)	145
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2066 ).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kang, S.-S., Li, H.-L., Zeng, H.-S. & Wang, H.-B. (2008). Acta Cryst. E64, o1125.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y., Wu, W.-N. & Yang, Z.-Y. (2009). X-ray Struct. Anal. Online, 25, 33-34.
Wang, Y., Yang, Z.-Y. & Chen, Z.-N. (2008). Bioorg. Med. Chem. Lett., 18, 298-303.

organic compounds