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

Volume 64
Part 5
Pages o867-o868
May 2008

Received 12 April 2008
Accepted 15 April 2008
Online 18 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.129
Data-to-parameter ratio = 16.7
Details

(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 and Amjid Iqbal ^a

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cDepartment of Chemistry, F.C. University, Lahore 54600, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

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-HO hydrogen bonds link the molecules into centrosymmetric R₂²(10) dimers. There are C-H [pi] interactions between benzene and pyrrole rings and a benzene C-H group. A weak [pi] - [pi] interaction between the pyrrole rings [centroid-centroid distance 3.8515 (11) Å] further stabilizes the structure. There is also a [pi] 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, P 2₁ /c
a = 13.0401 (7) Å
b = 5.6326 (3) Å
c = 15.6857 (8) Å
= 94.979 (3)°
V = 1147.76 (10) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.128
S = 1.02
3081 reflections
185 parameters
All H-atom parameters refined
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3-H3CgAⁱⁱ	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6-H6CgBⁱⁱⁱ	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . CgA and CgB are the centroids of the C1-C6 and N1/C10-C13 rings, respectively.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HK2452 ).

Acknowledgements

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

References

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organic compounds