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Acta Cryst. (2007). E63, o3939    [ doi:10.1107/S1600536807041852 ]

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

Z.-Q. Gong and Y.-L. Shen

Abstract top

In the title compound, C4H13NO, the pyrrole and benzene rings are almost coplanar, with a dihedral angle of 2.90 (1)° between them. In the crystal structure, molecules form centrosymmetric dimers through N-H...O hydrogen-bonding interactions. Neighbouring molecular pairs are held together by face-to-face [pi]-[pi] stacking interactions between adjacent pyrrole rings [perpendicular interplanar distance = 3.3948 (3) Å and centroid-to-centroid distance = 3.723 (2) Å], forming one-dimensional chains along the b axis.

Comment top

Chalcones have attracted considerable interest as a template in the development of biology. The anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000; Opletalova & Sedivy, 1999). The objective of this study therefore synthesize and elucidate the crystal structure of a new chalcone compound, (I), Fig. 1.

The pyrrole ring, benzene ring and the enone group of the molecule containing atoms O1, C5, C6 and C7, are almost co-planar with the maximum deviation 0.0702 Å for C7. The short H6···H9 (2.25 Å) contact causes the bond angles C7—C8—C9 [123.1 (2)°] C6—C7—C8 [127.7 (1)°] to deviate significantly from 120°.

In the crystal, molecules form inversion related dimers through N—H···O hydrogen bonds. Neighboring pairs are further linked by face-to-face π–π stacking interactions between adjacent pyrrole rings [perpendicular interplanar distance 3.3948 (3) Å and centroid-to-centroid distance 3.723 (2) Å], forming one-dimensional chains, Fig. 2.

Related literature top

For details of the biological properties of chalcones, see: Dimmock et al. (1999); Go et al. (2005); Opletalova (2000); Opletalova & Sedivy (1999). For related structures, see: Kumaran et al. (1996); Shanmuga Sundara Raj et al., (1997, 1998).

Experimental top

2-Acetylpyrrole (4.36 g, 40.0 mmol) was added to a solution of p-tolualdehyde (2.42 g, 20.0 mmol) in methanol (130 ml). Potassium hydroxide (2.24 g, 40 mmol) and ammonia (25%, 100 ml) were then added to the solution and refluxed for 36 h. The yellow precipitate that formed was removed by vacuum filtration, washed with water to neutral pH. The product was recrystallized from chloroform/ethanol (3:1) to yield 2.10 g (49%) of the title compound.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and N—H = 0.86 Å, Uiso = 1.2Ueq(C or N) for aromatic, ethylene and nitrogen; 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram showing the N—H····O hydrogen bonding and face-to-face π–π stacking interactions interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
3-(4-Methylphenyl)-1-(2-pyrrolyl)prop-2-en-1-one top
Crystal data top
C14H13NOF000 = 448
Mr = 211.25Dx = 1.217 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 1908 reflections
a = 8.6236 (11) Åθ = 2.4–26.2º
b = 5.6273 (7) ŵ = 0.08 mm−1
c = 23.958 (3) ÅT = 295 (2) K
β = 97.305 (2)ºPrism, yellow
V = 1153.2 (3) Å30.43 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer		2241 independent reflections
Radiation source: fine-focus sealed tube1757 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 295(2) Kθmax = 26.0º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.892, Tmax = 0.985k = −6→6
6514 measured reflectionsl = −29→29
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.145  w = 1/[σ2(Fo2) + (0.0733P)2 + 0.198P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2241 reflectionsΔρmax = 0.22 e Å−3
146 parametersΔρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H13NOV = 1153.2 (3) Å3
Mr = 211.25Z = 4
Monoclinic, P21/cMo Kα
a = 8.6236 (11) ŵ = 0.08 mm−1
b = 5.6273 (7) ÅT = 295 (2) K
c = 23.958 (3) Å0.43 × 0.22 × 0.18 mm
β = 97.305 (2)º
Data collection top
Bruker APEX area-detector
diffractometer		2241 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1757 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.985Rint = 0.022
6514 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051146 parameters
wR(F2) = 0.145H-atom parameters constrained
S = 1.05Δρmax = 0.22 e Å−3
2241 reflectionsΔρmin = −0.20 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41397 (15)0.4506 (2)0.42156 (5)0.0652 (4)
N10.65056 (16)0.2223 (3)0.49341 (6)0.0550 (4)
H10.62090.35070.50840.066*
C10.10198 (19)−0.0007 (3)0.15386 (7)0.0524 (4)
C20.2228 (2)−0.1227 (3)0.18472 (8)0.0610 (5)
H20.2580−0.26380.17050.073*
C30.2927 (2)−0.0405 (3)0.23608 (8)0.0628 (5)
H30.3739−0.12690.25580.075*
C40.24344 (18)0.1698 (3)0.25891 (7)0.0500 (4)
C50.1241 (2)0.2946 (3)0.22729 (7)0.0565 (5)
H50.09030.43780.24090.068*
C60.0545 (2)0.2104 (3)0.17596 (7)0.0587 (5)
H6−0.02570.29730.15590.070*
C70.0241 (2)−0.0992 (4)0.09886 (8)0.0699 (6)
H7A0.0887−0.06880.06980.105*
H7B−0.0757−0.02410.08930.105*
H7C0.0098−0.26740.10240.105*
C80.30938 (19)0.2592 (3)0.31416 (7)0.0532 (4)
H80.27680.40980.32370.064*
C90.40985 (19)0.1515 (3)0.35225 (7)0.0566 (5)
H90.44500.00040.34430.068*
C100.46818 (18)0.2609 (3)0.40658 (7)0.0521 (4)
C110.59111 (18)0.1372 (3)0.44173 (7)0.0495 (4)
C120.6710 (2)−0.0694 (3)0.43344 (8)0.0589 (5)
H120.6556−0.16640.40180.071*
C130.7789 (2)−0.1066 (4)0.48098 (8)0.0669 (5)
H130.8493−0.23200.48690.080*
C140.7621 (2)0.0753 (3)0.51726 (8)0.0627 (5)
H140.81860.09430.55270.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0716 (8)0.0628 (8)0.0578 (8)0.0086 (6)−0.0054 (6)−0.0152 (6)
N10.0557 (8)0.0583 (8)0.0494 (8)0.0015 (7)0.0008 (6)−0.0053 (7)
C10.0536 (9)0.0589 (10)0.0450 (9)−0.0076 (8)0.0074 (7)−0.0022 (8)
C20.0626 (10)0.0620 (11)0.0579 (11)0.0063 (9)0.0055 (8)−0.0173 (9)
C30.0562 (9)0.0701 (12)0.0590 (11)0.0146 (9)−0.0041 (8)−0.0137 (9)
C40.0478 (8)0.0540 (10)0.0478 (9)−0.0044 (7)0.0048 (7)−0.0057 (7)
C50.0698 (11)0.0469 (9)0.0520 (10)0.0039 (8)0.0050 (8)−0.0030 (8)
C60.0656 (10)0.0595 (10)0.0483 (10)0.0061 (8)−0.0025 (8)0.0035 (8)
C70.0754 (12)0.0805 (14)0.0513 (10)−0.0049 (10)−0.0013 (9)−0.0107 (9)
C80.0524 (9)0.0557 (10)0.0517 (10)−0.0034 (7)0.0072 (8)−0.0099 (8)
C90.0536 (9)0.0600 (10)0.0544 (10)0.0008 (8)−0.0001 (8)−0.0125 (8)
C100.0473 (8)0.0564 (10)0.0523 (10)−0.0052 (7)0.0055 (7)−0.0071 (8)
C110.0468 (8)0.0562 (10)0.0454 (9)−0.0066 (7)0.0044 (7)−0.0045 (7)
C120.0599 (10)0.0595 (11)0.0576 (10)−0.0013 (8)0.0093 (8)−0.0070 (9)
C130.0639 (11)0.0679 (12)0.0676 (12)0.0120 (9)0.0033 (9)0.0052 (10)
C140.0601 (10)0.0723 (12)0.0531 (10)0.0000 (9)−0.0025 (8)0.0044 (9)
Geometric parameters (Å, °) top
O1—C101.237 (2)C6—H60.9300
N1—C141.340 (2)C7—H7A0.9600
N1—C111.365 (2)C7—H7B0.9600
N1—H10.8600C7—H7C0.9600
C1—C21.382 (2)C8—C91.323 (2)
C1—C61.384 (2)C8—H80.9300
C1—C71.506 (2)C9—C101.470 (2)
C2—C31.379 (2)C9—H90.9300
C2—H20.9300C10—C111.446 (2)
C3—C41.393 (2)C11—C121.379 (2)
C3—H30.9300C12—C131.392 (2)
C4—C51.389 (2)C12—H120.9300
C4—C81.462 (2)C13—C141.362 (3)
C5—C61.381 (2)C13—H130.9300
C5—H50.9300C14—H140.9300
C14—N1—C11109.67 (15)C1—C7—H7C109.5
C14—N1—H1125.2H7A—C7—H7C109.5
C11—N1—H1125.2H7B—C7—H7C109.5
C2—C1—C6117.49 (15)C9—C8—C4127.73 (17)
C2—C1—C7120.48 (17)C9—C8—H8116.1
C6—C1—C7122.02 (16)C4—C8—H8116.1
C3—C2—C1121.66 (17)C8—C9—C10122.63 (17)
C3—C2—H2119.2C8—C9—H9118.7
C1—C2—H2119.2C10—C9—H9118.7
C2—C3—C4121.01 (16)O1—C10—C11121.51 (15)
C2—C3—H3119.5O1—C10—C9121.28 (15)
C4—C3—H3119.5C11—C10—C9117.21 (15)
C5—C4—C3117.21 (15)N1—C11—C12106.82 (14)
C5—C4—C8119.73 (15)N1—C11—C10121.50 (15)
C3—C4—C8123.05 (15)C12—C11—C10131.68 (15)
C6—C5—C4121.33 (16)C11—C12—C13107.66 (16)
C6—C5—H5119.3C11—C12—H12126.2
C4—C5—H5119.3C13—C12—H12126.2
C5—C6—C1121.27 (16)C14—C13—C12107.15 (17)
C5—C6—H6119.4C14—C13—H13126.4
C1—C6—H6119.4C12—C13—H13126.4
C1—C7—H7A109.5N1—C14—C13108.70 (16)
C1—C7—H7B109.5N1—C14—H14125.7
H7A—C7—H7B109.5C13—C14—H14125.7
C6—C1—C2—C31.0 (3)C8—C9—C10—O17.2 (3)
C7—C1—C2—C3−177.82 (18)C8—C9—C10—C11−172.94 (16)
C1—C2—C3—C40.1 (3)C14—N1—C11—C12−0.66 (19)
C2—C3—C4—C5−1.4 (3)C14—N1—C11—C10179.84 (15)
C2—C3—C4—C8177.45 (18)O1—C10—C11—N11.2 (3)
C3—C4—C5—C61.6 (3)C9—C10—C11—N1−178.62 (15)
C8—C4—C5—C6−177.28 (16)O1—C10—C11—C12−178.12 (17)
C4—C5—C6—C1−0.5 (3)C9—C10—C11—C122.0 (3)
C2—C1—C6—C5−0.8 (3)N1—C11—C12—C130.1 (2)
C7—C1—C6—C5178.01 (18)C10—C11—C12—C13179.52 (18)
C5—C4—C8—C9171.77 (17)C11—C12—C13—C140.5 (2)
C3—C4—C8—C9−7.0 (3)C11—N1—C14—C131.0 (2)
C4—C8—C9—C10179.85 (16)C12—C13—C14—N1−0.9 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.8525 (19)151
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.8525 (19)151
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

The authors thank Jiangxi Science and Technology Normal University for supporting this study.

references
References top

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Go, M. L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 481–499.

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Shanmuga Sundara Raj, S., Ponnuswamy, M. N., Shanmugam, G. & Nanjundan, S. (1998). Acta Cryst. C54, 541–542.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.