Dimethyl 3,5-diethyl-1H-pyrrole-2,4-dicarboxyl­ate

Lu, G.-F.; Lin, W.-S.; Zhu, W.-H.; Ou, Z.-P.

doi:10.1107/S1600536811028352

Volume 67
Part 8
Page o2097
August 2011

Received 29 June 2011
Accepted 15 July 2011
Online 23 July 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.118
Data-to-parameter ratio = 14.7
Details

Dimethyl 3,5-diethyl-1H-pyrrole-2,4-dicarboxylate

Gui-Fen Lu,^a Wen-Sheng Lin,^a Wei-Hua Zhu ^a and Zhong-Ping Ou ^a ^*

^aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
Correspondence e-mail: zpou2011@126.com

The title pyrrole derivative, C₁₂H₁₇NO₄, consists of a pyrrole ring with two diagonally attached methoxycarbonyl groups and two diagonally attached ethyl groups. The two carbonyl groups are approximately in the same plane as the pyrrole ring, making dihedral angles of 3.50 (19) and 6.70 (19)°. In the crystal, adjacent molecules are assembled into dimers in a head-to-head mode by pairs of intermolecular N-HO hydrogen bonds.

Related literature

For applications of polysubstituted pyrroles, see: Brockmann & Tour (1995); Guilard et al. (2001); Trofimov et al. (2004). For related structures, see: Takaya et al. (2001). For background to complexes of pyrrole derivatives, see: Fan et al. (2008); Ou et al. (2009); Paixão et al. (2003); Yamamoto et al. (1986).

Experimental

Crystal data

C₁₂H₁₇NO₄
M_r = 239.27
Monoclinic, P 2₁ /c
a = 4.4697 (7) Å
b = 14.616 (2) Å
c = 19.784 (3) Å
= 90.467 (2)°
V = 1292.4 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.982, T_max = 0.991
6296 measured reflections
2285 independent reflections
1977 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.118
S = 1.08
2285 reflections
155 parameters
1 restraint
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO4ⁱ	0.85	2.07	2.8773 (15)	160
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2335 ).

Acknowledgements

This work was supported by the Natural Science Foundation of China (No. 21001054) and the Natural Science Fund for Colleges and Universities in Jiangsu Province (No. 10KJB150003)

References

Brockmann, T. W. & Tour, J. M. (1995). J. Am. Chem. Soc. 117, 4437-4447.
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Fan, H., Peng, J. N., Hamann, M. T. & Hu, J. F. (2008). Chem. Rev. 108, 264-287.
Guilard, R., Gross, C. P., Bolze, F., Jerome, F., Ou, Z. P., Shao, J. G., Fischer, J., Weiss, R. & Kadish, K. M. (2001). Inorg. Chem. 40, 4845-4855.
Ou, Z. P., Zhu, W. H., Zhou, F., Zhao, X. F. & Ji, X. L. (2009). Fine Chem. 26, 609-612.
Paixão, J. A., Ramos Silva, M., Matos Beja, A., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. d'A. (2003). Acta Cryst. E59, o94-o96.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Takaya, H., Kojima, S. & Murahashi, S. I. (2001). Org. Lett. 3, 421-424.
Trofimov, B. A., Sobenina, L. N., Demenev, A. P. & Mikhaleva, A. (2004). Chem. Rev. 104, 2481-2506.
Yamamoto, N., Machida, K., Taga, T. & Ogoshi, H. (1986). Acta Cryst. C42, 1573-1576.

organic compounds