(2E)-3-(4-Chloro­phen­yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one

Mujahid Hussain Bukhari; Hamid Latif Siddiqui; M Nawaz Tahir; Muhammad Ashraf Chaudhary; Amjid Iqbal

doi:10.1107/S1600536808010362

. 2008 Apr 18;64(Pt 5):o867–o868. doi: 10.1107/S1600536808010362

(2E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one

Mujahid Hussain Bukhari ^a, Hamid Latif Siddiqui ^a, M Nawaz Tahir ^b,^*, Muhammad Ashraf Chaudhary ^c, Amjid Iqbal ^a

PMCID: PMC2961151 PMID: 21202354

Abstract

In the molecule of the title compound, C₁₃H₁₀ClNO, the benzene and pyrrole rings are oriented at a dihedral angle of 7.37 (12)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric R ₂ ²(10) dimers. There are C—H⋯π interactions between benzene and pyrrole rings and a benzene C—H group. A weak π–π interaction between the pyrrole rings [centroid–centroid distance 3.8515 (11) Å] further stabilizes the structure. There is also a π interaction between the pyrrole ring and the carbonyl group, with a carbon–centroid distance of 3.4825 (18) Å.

Related literature

For general background, see: Varga et al. (2003 ▶); Katritzky & Rees (1984 ▶); Wu et al. (2003 ▶); Nam et al. (2003 ▶); Sondhi et al. (2005 ▶); Miyazaki et al. (2005 ▶). For related literature, see: Powers et al. (1998 ▶); Hu et al. (2006 ▶); Wang et al. (2005 ▶); Zeng & Cen (2006 ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₀ClNO
M _r = 231.67
Monoclinic,
a = 13.0401 (7) Å
b = 5.6326 (3) Å
c = 15.6857 (8) Å
β = 94.979 (3)°
V = 1147.76 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 (2) K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.903, T _max = 0.935
13745 measured reflections
3081 independent reflections
2180 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.128
S = 1.02
3081 reflections
185 parameters
All H-atom parameters refined
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010362/hk2452sup1.cif

e-64-0o867-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010362/hk2452Isup2.hkl

e-64-0o867-Isup2.hkl^{(148.1KB, 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	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3⋯CgAⁱⁱ	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6⋯CgBⁱⁱⁱ	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . CgA and CgB are the centroids of the C1–C6 and N1/C10–C13 rings, respectively.

Acknowledgments

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer.

supplementary crystallographic information

Comment

Chalcones are 1,3-diaryl α,β-unsaturated compounds commonly used as starting materials for the synthesis of several biologically active compounds like pyrimidines and imidazoles (Varga et al., 2003). Most of the chalcones and their derivatives show biological activities such as antimicrobial (Katritzky & Rees, 1984), anti-AIDS (Wu et al., 2003), antimalarial (Nam et al., 2003), anti-inflammatory and analgesic (Sondhi et al., 2005) and antitumor (Miyazaki et al., 2005). While synthesizing different pyrimidine based compounds, we prepared the fine crystals of the title compound, (I), with known method (Powers et al., 1998). We report herein its crystal structure.

The crystal structures of 3-(4-chlorophenyl)-1-(3,4-dimethyl-2,5-dihydro-1H- pyrrol-1-yl)prop-2-enone, (II) (Hu et al., 2006), methyl-3-(1H-pyrrol-2-yl- carboxamido)propionate, (III) (Zeng & Cen, 2006) and 1,3-bis(4-chlorophenyl)- prop-2-en-1-one, (IV) (Wang et al., 2005) have been reported, previously. The title compound, (I), contains the moieties involved in these reported structures.

In the molecule of (I), (Fig. 1), the bond lengths N1-C10 [1.3711 (19) Å], N1-C13 [1.338 (3) Å] and C11-C12 [1.388 (3) Å] are reported as 1.457 (5), 1.461 (5) and 1.328 (6) Å in (II) and 1.369 (2), 1.349 (3) and 1.398 (3) Å in (III), respectively. Rings A (C1-C6) and B (N1/C10-C13) are, of course, planar and they are oriented at a dihedral angle of 7.37 (12)°. So, they are nearly coplanar. The planar central moiety (O1/C7-C9) is oriented with respect to rings A and B at dihedral angles of 8.92 (12)° and 1.94 (15)°, respectively.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric R₂²(10) dimers (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The C—H···π interactions (Table 1) and π—π interactions between B rings CgB···CgB^iv [symmetry code: (iv) -x, -y, 1 - z] further stabilize the structure, with a centroid-centroid distance of 3.8515 (11) Å. There is also a π interaction between the ring B at -x, -y, 1 - z and the carbonyl moiety, with C9-centroid distance of 3.4825 (18) Å.

Experimental

For the preparation of the title compound, a mixture of 4-chlorobenzaldehyde (1.4 g, 10 mmol) and 2-acetyl pyrrole (1.09 g, 10 mmol) was added to MeOH (20 ml) and stirred for 10 min at room temperature. Then, aqueous NaOH solution (10%, 4 ml) was added dropwise with continuous stirring at ambient temperature for 30 min. Light yellow precipitates appeared, to which cold water (40 ml) was added. Yellow colored powder was obtained from the filtrate, which was washed with cold MeOH, and then dried. The residue was recrystallized by dissolving in CHCl₃ (10 ml) and adding n-hexane dropwise. Fine yellow crystals were obtained (yield; 1.7 g, 73%, m.p. 420-422 K).