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Volume 70 
Part 1 
Pages o35-o36  
January 2014  

Received 6 December 2013
Accepted 6 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 16.0
Details
Open access

2-Isopropyl-5-methyl­cyclo­hexyl 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 cP.P.S.F.T. Department, Central Food Technplogy Research institute, Mysore 570 005, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C20H25NO2, the cyclo­hexyl ring adopts a slightly disordered chair conformation. The dihedral angle between the mean planes of the quinoline ring and the carboxyl­ate group is 22.2 (6)°. In the crystal, weak C-H...N inter­actions make chains along [010].

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: Fazal et al. (2012[Fazal, E., Jasinski, J. P., Krauss, S. T., Sudha, B. S. & Yathirajan, H. S. (2012). Acta Cryst. E68, o3231-o3232.], 2013a[Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013a). Acta Cryst. E69, o1842-o1843.],b[Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013b). Acta Cryst. E69, o1841.],c[Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013c). Acta Cryst. E69, o1853-o1854.]); 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 puckering parameters, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C20H25NO2

  • Mr = 311.41

  • Orthorhombic, P 21 21 21

  • a = 9.31412 (17) Å

  • b = 11.9669 (2) Å

  • c = 15.4894 (3) Å

  • V = 1726.47 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.60 mm-1

  • T = 173 K

  • 0.38 × 0.32 × 0.24 mm

Data collection
  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]). Tmin = 0.921, Tmax = 1.000

  • 11010 measured reflections

  • 3389 independent reflections

  • 3281 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.04

  • 3389 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); 1372 Friedel pairs

  • Absolute structure parameter: -0.01 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...N1i 0.95 2.56 3.509 (2) 174
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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: TK5278 ).


Acknowledgements

EF thanks CFTRI, Mysore, and Yuvaraja's College, UOM, for providing research facilities, and is grateful to Mr J. R. Manjunatha, PPSFT, CFTRI, for recording 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, Oxfordshire, England.
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603.  [CSD] [CrossRef] [IUCr Journals]
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031-1035.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
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.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013a). Acta Cryst. E69, o1842-o1843.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013b). Acta Cryst. E69, o1841.  [CSD] [CrossRef] [IUCr Journals]
Fazal, E., Kaur, M., Sudha, B. S., Nagarajan, S. & Jasinski, J. P. (2013c). Acta Cryst. E69, o1853-o1854.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [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]
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.  [CrossRef] [ChemPort]
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.  [CrossRef]
Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595-3607.  [CrossRef] [PubMed] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Robert, A. & Meunier, B. (1998). Chem. Soc. Rev. 27, 273-279.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Solomon, V. R. & Lee, H. (2011). Curr. Med. Chem. 18, 1488-1508.  [Web of Science] [ChemPort] [PubMed]


Acta Cryst (2014). E70, o35-o36   [ doi:10.1107/S1600536813033060 ]

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