3-(4-Methoxy­phen­yl)-1-(2-pyrrol­yl)prop-2-en-1-one

Dong-Qing Li

doi:10.1107/S160053680802864X

. 2008 Sep 13;64(Pt 10):o1920. doi: 10.1107/S160053680802864X

3-(4-Methoxyphenyl)-1-(2-pyrrolyl)prop-2-en-1-one

Dong-Qing Li ^a,^*

PMCID: PMC2959486 PMID: 21201128

Abstract

The title molecule, C₁₄H₁₃NO₂, is almost flat with a dihedral angle of 8.0 (1)° between the pyrrole and benzene rings. The central C₃O ketone unit has an s-cis conformation and is also coplanar with a torsion angle of −0.6 (3) °. An intramolecular C—H⋯O hydrogen bond generates an S(5) ring motif. In addition, the methoxy group is coplanar with the attached benzene ring. In the crystal structure, neighboring molecules are paired through N—H⋯O hydrogen bonds into centrosymmetric dimers with an R ² ₂(10) motif.

Related literature

For the pharmaceutical and biological properties of chalcones, see: Lin et al. (2002 ▶); Modzelewska et al. (2006 ▶); Opletalova (2000 ▶); Opletalova & Sedivy (1999 ▶); Sogawa et al. (1994 ▶). For chalcones as non-linear optical materials, see: Agrinskaya et al. (1999 ▶); Indira et al. (2002 ▶). For related structures, see: Bukhari et al. (2008 ▶); Fun et al. (2008 ▶); Gong, et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₂
M _r = 227.25
Monoclinic,
a = 5.0815 (7) Å
b = 17.172 (3) Å
c = 13.973 (2) Å
β = 97.878 (3)°
V = 1207.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.988
5842 measured reflections
2369 independent reflections
1809 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.124
S = 1.05
2369 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802864X/cs2091sup1.cif

e-64-o1920-sup1.cif^{(15.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802864X/cs2091Isup2.hkl

e-64-o1920-Isup2.hkl^{(116.4KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.93	2.52	2.838 (2)	100
N1—H1⋯O1ⁱ	0.86	2.03	2.8314 (17)	155

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Yulin Normal University for supporting this study.

supplementary crystallographic information

Comment

Chalcone derivatives have recently attracted extensive interest due to possessing a wide variety of pharmaceutical (Lin et al., 2002; Modzelewska et al., 2006; Sogawa et al., 1994) and biological properties (Opletalova, 2000; Opletalova & Sedivy, 1999). Some substituted chalcones also exhibit the potential applications as non-linear optical materials (Agrinskaya et al., 1999; Indira et al., 2002). Considering the importance of these types of compounds, a new chalcone compound was synthesized and its crystal structure is reported here.

The molecular structure of the title molecule (Fig. 1) is almost planar as indicated by a dihedral angle of 8.0 (1) ° between the pyrrole and benzene rings. The central O1/C5/C6/C7 ketone motif exhibits an s-cis conformation as usual in other related chalcone derivatives (Bukhari et al., 2008; Fun et al., 2008; Gong, et al., 2008;) and also coplanar with a torsion angle of -0.6 (3) °, meanwhile, O1 atom acts as an acceptor and is involved in an intramolecular C—H···O hydrogen bond (Table 1) to generate an S(5) ring motif. In the crystal packing, the compound can be stabilized by intermolecular N—H···O hydrogen bonds with –NH groups as donors to form centrosymmetric dimers with an R²₂(10) motif as shown in Fig. 2.

Experimental

The title compound was synthesized by the condensation of 2-acetylpyrrole (1.09 g, 10.0 mmol) and 4-methoxybenzaldehyde (1.06 g, 5.0 mmol) in methanol (30 ml) and ammonia (25%, 25 ml) in the presence of sodium hydroxide (0.56 g, 10 mmol). After refluxed at 358 K for 8 h, the contents of the flask were cooled to give a yellow crude precipitate which was separated by filtration, washed with water and iced ethanol. Recrystallization from ethanol afforded yellow prism-like crystals. Yield: 0.85 g (74.8%).