4-[2-(4-Fluoro­phen­yl)-1H-pyrrol-3-yl]pyridine

Abu Thaher, B.; Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S160053680900364X

Volume 65
Part 3
Page o457
March 2009

Received 23 January 2009
Accepted 29 January 2009
Online 4 February 2009

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.120
Data-to-parameter ratio = 13.3
Details

4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine

Bassam Abu Thaher,^a Pierre Koch,^b Dieter Schollmeyer ^c and Stefan Laufer ^b ^*

^aFaculty of Science, Chemistry Department, Islamic University of Gaza, Gaza Strip, Palestinian Territories,^bInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^cDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: stefan.laufer@uni-tuebingen.de

In the crystal structure of the title compound, C₁₅H₁₁FN₂, the pyrrole ring makes dihedral angles of 33.19 (9) and 36.33 (10)° with the pyridine and 4-fluorophenyl rings, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° with the 4-fluorophenyl ring. In the crystal structure, an N-HN hydrogen bond joins the molecules into chains.

Related literature

Many 1-(4-fluorophenyl)-2-(pyridin-4-yl)pyrrol derivatives have been prepared and their biological activities studied; see: de Laszlo et al. (1998); Revesz et al. (2000, 2002); Qian et al. (2006). For the synthesis of the title compound, see: Qian et al. (2006).

Experimental

Crystal data

C₁₅H₁₁FN₂
M_r = 238.26
Orthorhombic, P b c a
a = 9.2966 (7) Å
b = 8.1966 (5) Å
c = 30.5738 (19) Å
V = 2329.7 (3) Å³
Z = 8
Cu K radiation
= 0.76 mm^-1
T = 193 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
2175 measured reflections
2175 independent reflections
1744 reflections with I > 2(I)
3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.120
S = 1.03
2175 reflections
164 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N16ⁱ	0.93	1.97	2.8696 (19)	161
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2858 ).

Acknowledgements

The authors thank the Alexander von Humbolt Foundation (AvH) for funding.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Laszlo, S. E. de, Visco, D., Agarwal, L., Chang, L., Chin, J., Croft, G., Forsyth, A., Fletcher, D., Frantz, B., Hacker, C., Hanlon, W., Harper, C., Kostura, M., Li, B., Luell, S., MacCoss, M., Mantlo, N., O'Neill, E. A., Orevillo, C., Pang, M., Parsons, J., Rolando, A., Sahly, Y., Sidler, K., Widmer, W. R. & O'Keefe, S. J. (1998). Bioorg. Med. Chem. Lett. 8, 2689-2694.
Qian, X., Liang, G.-B., Feng, D., Fisher, M., Crumley, T., Rattray, S., Dulski, P. M., Gurnett, A., Leavitt, P. S., Liberator, P. A., Misura, A. S., Samaras, S., Tamas, T., Schmatz, D. M., Wyvratt, M. & Biftu, T. (2006). Bioorg. Med. Chem. Lett. 16, 2817-2821.
Revesz, L., Di Padova, F. E., Buhl, T., Feifel, R., Gram, H., Hiestand, P., Manning, U., Wolf, R. & Zimmerlin, A. G. (2002). Bioorg. Med. Chem. Lett. 12, 2109-2112.
Revesz, L., Di Padova, F. E., Buhl, T., Feifel, R., Gram, H., Hiestand, P., Manning, U. & Zimmerlin, A. G. (2000). Bioorg. Med. Chem. Lett. 10, 1261-1264.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds