2-(4-Chloro­anilino)pyridine

Fairuz, M.Z.A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536808026317

Volume 64
Part 9
Page o1800
September 2008

Received 13 August 2008
Accepted 14 August 2008
Online 20 August 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.073
wR = 0.201
Data-to-parameter ratio = 13.2
Details

2-(4-Chloroanilino)pyridine

M. Zainal Abidin Fairuz,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The two aromatic rings of each of the four independent molecules in the asymmetric unit of the title compound, C₁₁H₉ClN₂, are approximately coplanar; the four molecules are arranged into two amino-pyridyl N-HN hydrogen-bonded pairs. The structure has a 15% twin component related by a twofold rotation about [100].

Related literature

The title compound exhibits fluorescence; see: Abdullah (2005); Kawai et al. (2001); Mohd Salleh et al. (2007). For the use of PLATON in the preparation of the diffraction data, see: Spek (2003).

Experimental

Crystal data

C₁₁H₉ClN₂
M_r = 204.65
Triclinic, $[P \overline 1]$
a = 7.3926 (3) Å
b = 15.3577 (5) Å
c = 17.6093 (6) Å
= 73.723 (2)°
= 87.360 (3)°
= 87.128 (3)°
V = 1915.6 (1) Å³
Z = 8
Mo K radiation
= 0.35 mm^-1
T = 100 (2) K
0.26 × 0.16 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.913, T_max = 0.989
14371 measured reflections
6679 independent reflections
4259 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.073
wR(F²) = 0.201
S = 1.04
6679 reflections
506 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nN3	0.88	2.19	3.019 (5)	156
N4-H4nN1	0.88	2.17	3.010 (5)	160
N6-H6nN7	0.88	2.13	2.968 (5)	158
N8-H8nN5	0.88	2.25	3.096 (5)	161

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2115 ).

Acknowledgements

We thank Dr Sean Parkin of the University of Kentucky for discussion of the twinning problem, and we thank the University of Malaya for supporting this study (grant No. FS358/2008 A).

References

Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.
Mohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci. 11, 229-236.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds