3-Phenyl-1-(pyrrol-2-yl)prop-2-en-1-one

Zhen-Qi Gong; Gou-Sheng Liu; Hong-Ying Xia

doi:10.1107/S1600536807063489

. 2007 Dec 6;64(Pt 1):o151. doi: 10.1107/S1600536807063489

3-Phenyl-1-(pyrrol-2-yl)prop-2-en-1-one

Zhen-Qi Gong ^a,^*, Gou-Sheng Liu ^a, Hong-Ying Xia ^a

PMCID: PMC2915219 PMID: 21200716

Abstract

The title molecule, C₁₃H₁₁NO, is almost flat, the angle between the pyrrole and the phenyl rings being 10.9 (1)°. The atoms of the central C₃O unit are coplanar, with a mean deviation from the plane of 0.001 (1) Å. The angles between this plane and the pyrrole and phenyl rings are 3.3 (1) and 8.0 (1)°, respectively. The molecules form centrosymmetric dimers through a pair of N—H⋯O hydrogen bonds with an R ² ₂(10) motif.

Related literature

For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Lin et al. (2002 ▶); Lunardi et al. (2003 ▶); Opletalova (2000 ▶). For other related literature, see: Gong & Shen (2007 ▶); Kumaran et al. (1996 ▶); Shanmuga Sundara Raj et al. (1997 ▶, 1998 ▶). For a description of hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C₁₃H₁₁NO
M _r = 197.23
Monoclinic,
a = 19.848 (4) Å
b = 5.6435 (12) Å
c = 19.325 (4) Å
β = 101.535 (4)°
V = 2120.9 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.34 × 0.13 × 0.11 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.974, T _max = 0.991
5274 measured reflections
2069 independent reflections
1164 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.137
S = 1.00
2069 reflections
136 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, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2002 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063489/fb2072sup1.cif

e-64-0o151-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063489/fb2072Isup2.hkl

e-64-0o151-Isup2.hkl^{(101.9KB, 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
N1—H1⋯O1ⁱ	0.86	2.02	2.817 (2)	155
C7—H7⋯O1	0.93	2.51	2.835 (3)	101

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Jiangxi Science and Technology Normal University for the support of this study.

supplementary crystallographic information

Comment

Chalcone derivatives possess wide variety of pharmaceutical properties, such as anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory ones (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000). Some of the substituted chalcones are also reported to possess antileishmanial (Chen et al., 1999), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003) activities. As a part of our ongoing efforts in the chalcone compounds (Gong & Shen, 2007), the title compound is reported here for the first time.

In the title compound, C₁₃H₁₁NO, the bond lengths and angles are usual. The –NH groups are involved as donors to form centrosymmetric dimers with a motif R²₂(10) through N—H···O hydrogen bonds (Etter et al., 1990) - (Fig. 2). There is a pyrrole-H···π-phenyl-ring interaction as indicate the geometric parameters C2—H2···Centroid(phenyl) (1 - x, y, 3/2 - z) where the distance H···centroid and C2···centroid equal to 2.90 and 3.666 (3) Å, respectively, and the angle C2—H2···Centroid(phenyl) equals to 141° (Spek, 2003).

Experimental

2-Acetylpyrrole (2.18 g, 20.0 mmol) was added to a solution of benzaldehyde (1.06 g, 10.0 mmol) in methanol (65 ml). Then potassium hydroxide (1.12 g, 20 mmol) and ammonia (25%, 50 ml) were added to the solution and refluxed for 12 h. The resulting solution was cooled and the solvent was evaporated under vacuum to give an orange precipitate which was separated by filtration, washed with iced ethanol (95%) and water to pH = 7. Recrystallization from dichloromethane gave light yellow prism-like crystals with average size of about 1.50x0.35x0.25 mm. Yield: 0.89 g (45%).