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Volume 69 
Part 12 
Page o1841  
December 2013  

Received 24 November 2013
Accepted 24 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 13.8
Details
Open access

4-Chloro­phenyl quinoline-2-carboxyl­ate

aDepartment of Chemistry, Yuvaraja's College, Mysore 570 005, India,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,cP.P.S.F.T. Department, Central Food Technplogy Research institute, Mysore 570 005, India, and dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C16H10ClNO2, the dihedral angle between the quinoline ring system and the benzene ring is 14.7 (5)°. The carboxyl­ate group is twisted from the mean planes of the quinoline ring system and the benzene ring by 17.7 (5) and 32.1 (4)°, respectively. In the crystal, inversion dimers are formed with the molecules linked by pairs of weak C-H...O inter­actions arising from an activated aromatic C atom adjacent to the C-Cl bond, generating R22(14) loops.

Related literature

For related structures, see: Fazal et al. (2012[Fazal, E., Jasinski, J. P., Krauss, S. T., Sudha, B. S. & Yathirajan, H. S. (2012). Acta Cryst. E68, o3231-o3232.]); Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603.]); Jing & Qin (2008[Jing, L.-H. & Qin, D.-B. (2008). Z. Kristallogr. 223, 35-36.]); Jasinski et al. (2010[Jasinski, J. P., Butcher, R. J., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). J. Mol. Struct. 980, 172-181.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10ClNO2

  • Mr = 283.70

  • Monoclinic, P 21 /n

  • a = 6.38693 (18) Å

  • b = 16.8893 (5) Å

  • c = 12.2649 (4) Å

  • [beta] = 103.527 (3)°

  • V = 1286.33 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.63 mm-1

  • T = 173 K

  • 0.34 × 0.18 × 0.12 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.611, Tmax = 1.000

  • 7778 measured reflections

  • 2502 independent reflections

  • 2168 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.05

  • 2502 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...O1i 0.93 2.42 3.250 (2) 148
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (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.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7166 ).


Acknowledgements

EF thanks the CFTRI, Mysore and Yuvaraja's College, UOM, for providing research facilities. EF is grateful to Mr J. R. Manjunatha, PPSFT, CFTRI for the NMR spectra. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603.  [CSD] [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fazal, E., Jasinski, J. P., Krauss, S. T., Sudha, B. S. & Yathirajan, H. S. (2012). Acta Cryst. E68, o3231-o3232.  [CrossRef] [ChemPort] [IUCr Journals]
Jasinski, J. P., Butcher, R. J., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). J. Mol. Struct. 980, 172-181.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Jing, L.-H. & Qin, D.-B. (2008). Z. Kristallogr. 223, 35-36.  [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1841  [ doi:10.1107/S1600536813032054 ]

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