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

Abdullah M Asiri; Abdulrahman O Al-Youbi; Khalid A Alamry; Hassan M Faidallah; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811031941

. 2011 Aug 11;67(Pt 9):o2315. doi: 10.1107/S1600536811031941

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, Edward R T Tiekink ^c,^*

PMCID: PMC3200670 PMID: 22058943

Abstract

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—H⋯O and C—H⋯N interactions are further connected by C—H⋯π(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,
a = 7.6145 (3) Å
b = 8.4964 (6) Å
c = 9.7023 (6) Å
α = 64.898 (7)°
β = 89.859 (4)°
γ = 71.517 (5)°
V = 532.69 (5) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.106
S = 1.04
2336 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031941/hb6354sup1.cif

e-67-o2315-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031941/hb6354Isup2.hkl

e-67-o2315-Isup2.hkl^{(114.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11a⋯O2ⁱ	0.98	2.31	3.241 (2)	158
C9—H9⋯N1ⁱⁱ	0.95	2.62	3.557 (2)	171
C11—H11b⋯Cg1ⁱⁱⁱ	0.98	2.69	3.5332 (17)	144

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound (I) was studied in connection with the known biological activity of 2(1H)pyridone compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011), and was prepared from the condensation of the N-methylpyrrole-2-carboxaldehyde with ethyl cyanoacetate during an attempt to prepare a 2(1H)pyridone derivative.

The molecular structure of (I), Fig. 1, is, to a first approximation, planar with the r.m.s. deviation for all 15 non-H atoms being 0.145 Å. The major deviations from the least-squares plane are 0.214 (2) and -0.337 (2) Å for the C9 and C11 atoms, respectively, reflecting a small twist between the ethene and pyrrole rings [the C11—N2—C7—C6 torsion angle = -8.26 (18) °]. The conformation about the ethene [C4═C7 = 1.3594 (18) Å] bond is E. The carbonyl-O and cyano-N atoms are syn to each other.

In the crystal packing, molecules are linked into chains via C—H···O interactions involving a N-bound methyl-H and carbonyl-O, Table 1. Chains are linked into a linear tape via C—H···N interactions involving a pyrrole-H and cyano-N, Fig. 2. The tapes are consolidated into the three-dimensional architecture by C—H···π interactions, Fig. 3, involving another N-bound methyl-H as the donor to the pyrrole ring.

Experimental

A mixture of the N-methylpyrrole-2-carboxaldehyde (1.0 g,1 0 mmol), 2-methylcyclohexanone (1.12 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, the formed precipitate was filtered, washed with water, dried and recrystallized from ethanol to form yellow blocks. M.pt. 420–421 K.