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Volume 66 
Part 11 
Page o2987  
November 2010  

Received 26 September 2010
Accepted 26 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.166
Data-to-parameter ratio = 13.9
Details
Open access

[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and bDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
Correspondence e-mail: njutshs@126.com

The title compound, C19H16FNO, crystallizes with two independent molecules in the asymmetric unit. In the two molecules, the dihedral angles between the benzene and quinoline rings are 72.6 (5) and 76.2 (5)°, between the cyclopropane and quinoline rings they are 65.2 (5) and 66.0 (5)°, and between the benzene and cyclopropane rings they are 25.9 (5) and 33.9 (5)°. There are intermolecular O-H...O, O-H...N and C-H...O hydrogen bonds, as well as intramolecular C-H...O hydrogen bonds, which may be effective in stabilizing the crystal structure.

Related literature

For a related structure, see: Prasath et al. (2010[Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16FNO

  • Mr = 293.33

  • Monoclinic, P 21 /c

  • a = 10.069 (2) Å

  • b = 24.683 (5) Å

  • c = 13.275 (3) Å

  • [beta] = 111.97 (3)°

  • V = 3059.7 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: empirical (using intensity measurements) via [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.974, Tmax = 0.983

  • 5865 measured reflections

  • 5536 independent reflections

  • 3098 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.166

  • S = 1.00

  • 5536 reflections

  • 398 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 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
O1-H1A...N2i 0.85 2.04 2.849 (3) 159
O2-H2B...O1ii 0.82 2.10 2.909 (3) 170
C30-H30A...O1i 0.93 2.57 3.307 (3) 136
C37-H37B...O1i 0.97 2.59 3.372 (4) 138
C36-H36A...O2 0.98 2.49 3.117 (4) 121
C17-H17A...O1 0.98 2.55 3.168 (4) 121
C12-H12A...O2iii 0.93 2.42 3.318 (5) 161
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, y, z; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2333 ).


Acknowledgements

The authors thank the Center for Testing and Analysis, Nanjing University, for support.

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o2987  [ doi:10.1107/S1600536810043588 ]

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