7-[(Morpholin-4-yl)(phen­yl)meth­yl]quinolin-8-ol

Novina, J.J.; Vasuki, G.; Muthukumar, C.; Sabastiyan, A.; Crochet, A.; Fromm, K.M.

doi:10.1107/S1600536812049343

Volume 69
Part 1
Page o45
January 2013

Received 19 November 2012
Accepted 30 November 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.074
Data-to-parameter ratio = 12.7
Details

7-[(Morpholin-4-yl)(phenyl)methyl]quinolin-8-ol

J. Josephine Novina,^a G. Vasuki,^b ^* C. Muthukumar,^c A. Sabastiyan,^c A. Crochet ^d and K. M. Fromm ^e

^aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India,^bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India,^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli-19, India,^dFribourg Center for Nanomaterials, FriMat, University of Fribourg, Switzerland, and ^eDepartment of Chemistry, University of Fribourg, Switzerland
Correspondence e-mail: vasuki.arasi@yahoo.com

In the title compound, C₂₀H₂₀N₂O₂, the quinoline ring system makes dihedral angles of 81.05 (4) and 61.16 (5)° with the mean planes of the benzene and morpholine rings, respectively; the mean planes of the latter two rings make a dihedral angle of 83.59 (4)°. In the crystal, pairs of O-HN hydrogen bonds link neighbouring molecules related by a twofold rotation axis, generating R₂²(10) motifs.

Related literature

For the biological activity of quinoline derivatives, see: Thakur et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₀H₂₀N₂O₂
M_r = 320.38
Orthorhombic, A b a 2
a = 13.1537 (6) Å
b = 31.0875 (13) Å
c = 8.3175 (3) Å
V = 3401.2 (2) Å³
Z = 8
Cu K radiation
= 0.65 mm^-1
T = 200 K
0.60 × 0.32 × 0.17 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-SHAPE: Stoe & Cie, 2002) T_min = 0.696, T_max = 0.898
12678 measured reflections
2776 independent reflections
2696 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.074
S = 1.06
2776 reflections
218 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3
Absolute structure: Flack (1983), 1273 Friedel pairs
Flack parameter: -0.05 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN1ⁱ	0.85 (2)	2.01 (2)	2.7668 (14)	148 (18)
Symmetry code: (i) -x, -y+1, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2537 ).

Acknowledgements

The authors thank the Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Switzerland, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Thakur, A. S., Jha, A. K., Verma, P., Deshmukh, R., Devangan, D. & Chandy, A. (2010). Int. J. Compr. Pharm. 1, 1-4.

organic compounds