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Volume 69 
Part 10 
Page o1571  
October 2013  

Received 16 September 2013
Accepted 17 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.123
Data-to-parameter ratio = 16.5
Details
Open access

2-[(E)-(Morpholin-4-ylimino)methyl]-6-(morpholin-4-ylmethyl)phenol

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The title compound, C16H23N3O3, contains two morpholine rings, each of which adopts a chair conformation. The molecular conformation is stabilized by an intramolecular O-H...N hydrogen bond, leading to a S(6) ring. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C-H...O and C-H...[pi] interactions.

Related literature

For background to Schiff bases and their applications, see: Dhar & Taploo (1982[Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.]); Nelson et al. (2004[Nelson, T. D., Rosen, J. D., Brands, K. M. J., Craig, B., Huffman, M. A. & McNamara, J. M. (2004). Tetrahedron Lett. 45, 8917-8920.]); Silva et al. (2011[Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B. & de Fatima, A. (2011). J. Adv. Res. 2, 1-8.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H23N3O3

  • Mr = 305.37

  • Monoclinic, P 21 /c

  • a = 9.0074 (6) Å

  • b = 15.7781 (14) Å

  • c = 11.3083 (7) Å

  • [beta] = 99.052 (5)°

  • V = 1587.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.51 × 0.32 × 0.09 mm

Data collection
  • STOE IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.961, Tmax = 0.990

  • 23637 measured reflections

  • 3289 independent reflections

  • 1955 reflections with I > 2[sigma](I)

  • Rint = 0.089

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

  • wR(F2) = 0.123

  • S = 1.03

  • 3289 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C6-C11 benzene ring.

D-H...A D-H H...A D...A D-H...A
O2-H2...N2 0.82 1.91 2.636 (2) 146
C13-H13A...O3i 0.97 2.55 3.416 (3) 149
C4-H4A...Cg3i 0.97 2.87 3.646 (3) 138
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: TK5257 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nelson, T. D., Rosen, J. D., Brands, K. M. J., Craig, B., Huffman, M. A. & McNamara, J. M. (2004). Tetrahedron Lett. 45, 8917-8920.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B. & de Fatima, A. (2011). J. Adv. Res. 2, 1-8.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o1571  [ doi:10.1107/S160053681302566X ]

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