Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Asiri, A.M.; Al-Youbi, A.O.; Alamry, K.A.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811031941

Volume 67
Part 9
Page o2315
September 2011

Received 6 August 2011
Accepted 7 August 2011
Online 11 August 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.106
Data-to-parameter ratio = 16.9
Details

Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Abdullah M. Asiri,^a,^b ⁺ Abdulrahman O. Al-Youbi,^a Khalid A. Alamry,^a Hassan M. Faidallah,^a Seik Weng Ng ^c,^a and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia,^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The 15 non-H atoms of the title compound, C₁₁H₁₂N₂O₂, are approximately coplanar, the r.m.s. deviation being 0.145 Å. The major deviation from coplanarity is seen in a twist between the ethene (E configuration) and pyrrole rings [C-C-N-C torsion angle = -8.26 (18)°]. The carbonyl O and cyano N atoms are syn to each other. In the crystal, supramolecular linear tapes linked by C-HO and C-HN interactions are further connected by C-H [pi] (pyrrole) interactions.

Related literature

For background to the biological activity of 2(1H)pyridone compounds, see: Aly et al. (1991); Al-Saadi et al. (2005); Rostom et al. (2011).

Experimental

Crystal data

C₁₁H₁₂N₂O₂
M_r = 204.23
Triclinic, $[P \overline 1]$
a = 7.6145 (3) Å
b = 8.4964 (6) Å
c = 9.7023 (6) Å
= 64.898 (7)°
= 89.859 (4)°
= 71.517 (5)°
V = 532.69 (5) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.30 × 0.25 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.955, T_max = 1.000
4049 measured reflections
2336 independent reflections
1912 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.106
S = 1.04
2336 reflections
138 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2,C7-C10 ring.

D-HA	D-H	HA	DA	D-HA
C11-H11aO2ⁱ	0.98	2.31	3.241 (2)	158
C9-H9N1ⁱⁱ	0.95	2.62	3.557 (2)	171
C11-H11bCg1ⁱⁱⁱ	0.98	2.69	3.5332 (17)	144
Symmetry codes: (i) x-1, y+1, z; (ii) -x+1, -y+2, -z; (iii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6354 ).

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Saadi, S. M., Rostom, S. A. F. & Faid Allah, H. M. (2005). Alex. J. Pharm. Sci, 19, 15-21.
Aly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827-834.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Rostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. doi:10.1007/s00044-010-9469-0.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References