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

Sun, H.; Xu, H.; Li, Y.-L.

doi:10.1107/S1600536810043588

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 (C-C) = 0.005 Å
R = 0.058
wR = 0.166
Data-to-parameter ratio = 13.9
Details

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

Hongshun Sun,^a ^* Hong Xu ^b and Yu-Long Li ^a

^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-HO, O-HN and C-HO hydrogen bonds, as well as intramolecular C-HO hydrogen bonds, which may be effective in stabilizing the crystal structure.

Related literature

For a related structure, see: Prasath et al. (2010).

Experimental

Crystal data

C₁₉H₁₆FNO
M_r = 293.33
Monoclinic, P 2₁ /c
a = 10.069 (2) Å
b = 24.683 (5) Å
c = 13.275 (3) Å
= 111.97 (3)°
V = 3059.7 (13) Å³
Z = 8
Mo K radiation
= 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 scan (North et al., 1968) T_min = 0.974, T_max = 0.983
5865 measured reflections
5536 independent reflections
3098 reflections with I > 2(I)
R_int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.166
S = 1.00
5536 reflections
398 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN2ⁱ	0.85	2.04	2.849 (3)	159
O2-H2BO1ⁱⁱ	0.82	2.10	2.909 (3)	170
C30-H30AO1ⁱ	0.93	2.57	3.307 (3)	136
C37-H37BO1ⁱ	0.97	2.59	3.372 (4)	138
C36-H36AO2	0.98	2.49	3.117 (4)	121
C17-H17AO1	0.98	2.55	3.168 (4)	121
C12-H12AO2ⁱⁱⁱ	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); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds