Methyl 6-chloro­nicotinate

Xu, Y.; Yang, L.-L.; Yang, S.-Y.; Liu, J.

doi:10.1107/S1600536811053517

Volume 68
Part 1
Page o162
January 2012

Received 1 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.055
wR = 0.119
Data-to-parameter ratio = 15.1
Details

Methyl 6-chloronicotinate

Yong Xu,^a Ling-Ling Yang,^b Sheng-Yong Yang ^a and Jie Liu ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and ^bDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
Correspondence e-mail: liujie2011@scu.edu.cn

The molecule of the title compound, C₇H₆ClNO₂, is almost planar, with a dihedral angle of 3.34 (14)° between the COOMe group and the aromatic ring. In the crystal, the molecules are arranged into (1 $[\overline{1}]$ 2) layers by C-HN hydrogen bonds and there are [pi] - [pi] stacking interactions between the aromatic rings in adjacent layers [centroid-centroid distance 3.8721 (4) Å]

Related literature

For background to the synthesis of methyl 6-chloronicotinate, see: González et al. (2009); Rekha et al. (2009). For a related structure, see: Ma & Liu (2008).

Experimental

Crystal data

C₇H₆ClNO₂
M_r = 171.58
Triclinic, $[P \overline 1]$
a = 3.8721 (4) Å
b = 5.8068 (6) Å
c = 17.3721 (18) Å
= 95.563 (9)°
= 94.918 (8)°
= 104.657 (9)°
V = 373.64 (7) Å³
Z = 2
Mo K radiation
= 0.45 mm^-1
T = 293 K
0.30 × 0.30 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.037, T_max = 1.000
3068 measured reflections
1527 independent reflections
855 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.119
S = 0.99
1527 reflections
101 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1ⁱ	0.93	2.59	3.440 (4)	151
Symmetry code: (i) x-1, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2439 ).

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
González, M. A., Correa-Royero, J., Mesa, A. & Betancur-Galvis, L. (2009). Nat. Prod. Res. 23, 1485-1491.
Ma, Y. & Liu, Y.-L. (2008). Acta Cryst. E64, o1072.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Rekha, V. V., Ramani, M. V., Ratnamala, A., Rupakalpana, V., Subbaraju, G. V., Satyanarayana, C. & Rao, C. S. (2009). Org. Process Res. Dev. 13, 769-773.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds