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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 [sigma](C-C) = 0.002 Å
R = 0.028
wR = 0.074
Data-to-parameter ratio = 12.7
Details
Open access

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

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-H...N 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[Thakur, A. S., Jha, A. K., Verma, P., Deshmukh, R., Devangan, D. & Chandy, A. (2010). Int. J. Compr. Pharm. 1, 1-4.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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
  • C20H20N2O2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.696, Tmax = 0.898

  • 12678 measured reflections

  • 2776 independent reflections

  • 2696 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1273 Friedel pairs

  • Flack parameter: -0.05 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1i 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[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.


Acta Cryst (2013). E69, o45  [ doi:10.1107/S1600536812049343 ]

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