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Volume 68 
Part 11 
Pages o3231-o3232  
November 2012  

Received 19 October 2012
Accepted 23 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 14.5
Details
Open access

4-Methylphenyl quinoline-2-carboxylate

aDepartment of Chemistry, Yuvaraja's College, Mysore 570 005, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C17H13NO2, two molecules crystallize in the asymmetric unit. The dihedral angle between the mean planes of the quinoline and benzene rings are 78.3 (4) and 88.2 (3)°. The carboxylate group is twisted slightly from the quinoline ring by 7.1 (2) and 13.3 (4)°, respectively. In the crystal, weak C-H...O interactions are observed. Further stabilization is provided by weak [pi]-[pi] stacking interactions, with centroid-centroid distances of 3.564 (9)/3.689 (2) and 3.830 (1)/3.896 (5)Å, respectively.

Related literature

For heterocycles in natural products, see: Morimoto et al. (1991[Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.]); Michael (1997[Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.]). For heterocycles in fragrances and dyes, see: Padwa et al. (1999[Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595-3607.]). For heterocycles in biologically active compounds, see: Markees et al. (1970[Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.]); Campbell et al. (1988[Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031-1035.]). For quinoline alkaloids used as efficient drugs for the treatment of malaria, see: Robert & Meunier, (1998[Robert, A. & Meunier, B. (1998). Chem. Soc. Rev. 27, 273-279.]). For quinoline as a privileged scaffold in cancer drug discovery, see: Solomon & Lee (2011[Solomon, V. R. & Lee, H. (2011). Curr. Med. Chem. 18, 1488-1508.]). For related structures, see: Dobrzynska & Jerzykiewicz, (2004[Dobrzynska, D. & Jerzykiewicz, L. B. (2004). J. Chem. Crystallogr. 34, 51-55.]); 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.]). For bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13NO2

  • Mr = 263.28

  • Orthorhombic, P b c a

  • a = 11.5421 (2) Å

  • b = 17.3191 (3) Å

  • c = 26.6667 (5) Å

  • V = 5330.65 (16) Å3

  • Z = 16

  • Cu K[alpha] radiation

  • [mu] = 0.70 mm-1

  • T = 173 K

  • 0.22 × 0.14 × 0.12 mm

Data collection
  • Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.726, Tmax = 1.000

  • 34626 measured reflections

  • 5265 independent reflections

  • 4303 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.124

  • S = 1.02

  • 5265 reflections

  • 363 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15B-H15B...O2Ai 0.93 2.59 3.343 (2) 138
Symmetry code: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); 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: SHELXTL (Bruker, 2000[Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2377 ).


Acknowledgements

EF thanks Yuvaraja's college, UOM for providing the research facilities and also to Dr. S. Nagarajan, Senior Scientist at CFTRI for giving valuable suggestions. JPJ acknowledges the NSF-MRI program (grant No·CHE1039027) for funds to purchase the X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603.  [CSD] [CrossRef] [details]
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031-1035.  [CrossRef] [ChemPort] [PubMed] [ISI]
Dobrzynska, D. & Jerzykiewicz, L. B. (2004). J. Chem. Crystallogr. 34, 51-55.  [ISI] [CSD] [CrossRef] [ChemPort]
Jasinski, J. P., Butcher, R. J., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). J. Mol. Struct. 980, 172-181.  [ISI] [CSD] [CrossRef] [ChemPort]
Jing, L.-H. & Qin, D.-B. (2008). Z. Kristallogr. 223, 35-36.  [ChemPort]
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.  [CrossRef] [ChemPort] [PubMed] [ISI]
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.  [CrossRef] [ChemPort]
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.  [CrossRef]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595-3607.  [CrossRef] [PubMed] [ChemPort]
Robert, A. & Meunier, B. (1998). Chem. Soc. Rev. 27, 273-279.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Solomon, V. R. & Lee, H. (2011). Curr. Med. Chem. 18, 1488-1508.  [ISI] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3231-o3232   [ doi:10.1107/S1600536812044030 ]

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