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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 [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.119
Data-to-parameter ratio = 15.1
Details
Open access

Methyl 6-chloronicotinate

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-H...N 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[González, M. A., Correa-Royero, J., Mesa, A. & Betancur-Galvis, L. (2009). Nat. Prod. Res. 23, 1485-1491.]); Rekha et al. (2009[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.]). For a related structure, see: Ma & Liu (2008[Ma, Y. & Liu, Y.-L. (2008). Acta Cryst. E64, o1072.]).

[Scheme 1]

Experimental

Crystal data
  • C7H6ClNO2

  • Mr = 171.58

  • Triclinic, [P \overline 1]

  • a = 3.8721 (4) Å

  • b = 5.8068 (6) Å

  • c = 17.3721 (18) Å

  • [alpha] = 95.563 (9)°

  • [beta] = 94.918 (8)°

  • [gamma] = 104.657 (9)°

  • V = 373.64 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.037, Tmax = 1.000

  • 3068 measured reflections

  • 1527 independent reflections

  • 855 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.119

  • S = 0.99

  • 1527 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N1i 0.93 2.59 3.440 (4) 151
Symmetry code: (i) x-1, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[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.]); 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.  [ISI] [CrossRef] [ChemPort] [details]
González, M. A., Correa-Royero, J., Mesa, A. & Betancur-Galvis, L. (2009). Nat. Prod. Res. 23, 1485-1491.  [ISI] [PubMed]
Ma, Y. & Liu, Y.-L. (2008). Acta Cryst. E64, o1072.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o162  [ doi:10.1107/S1600536811053517 ]

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