[Journal logo]

Volume 69 
Part 6 
Pages o903-o904  
June 2013  

Received 24 April 2013
Accepted 8 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.086
Data-to-parameter ratio = 14.2
Details
Open access

4-[(E)-(4-Ethoxybenzylidene)amino]phenol

aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and eDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: suchada.c@psu.ac.th

The molecule of the title compound, C15H15NO2, adopts a trans conformation with respect to the methylidene C=N bond and is twisted with a dihedral angle of 26.31 (5)° between the two substituted benzene rings. The ethoxy group is almost coplanar with the bound benzene ring with a C-O-C-C torsion angle of -179.08 (9)°. In the crystal, molecules are linked by O-H...N hydrogen bonds and weak C-H...O interactions into chains propagating in the [011] and [01-1] directions. C-H...[pi] interactions are also present.

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For background to and applications of aza-stilbene, see: Cheng et al. (2010[Cheng, L.-X., Tang, J.-J., Luo, H., Jin, X.-L., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. & Zhou, B. (2010). Bioorg. Med. Chem. Lett. 20, 2417-2420.]); da Silva et al. (2011[Silva, C. M. da, da Silva, D. L., Martins, C. V. B., de Resende, M. A., Dias, E. S., Magalhaes, T. F. F., Rodrigues, L. P., Sabino, A. A., Alves, R. B. & de Fatima, A. (2011). Chem. Biol. Drug Des. 78, 810-815.]); Kabir et al. (2008[Kabir, M. S., Engelbrecht, K., Polanowski, R., Krueger, S. M., Ignasiak, R., Rott, M., Schwan, W. R., Stemper, M. E., Reed, K. D., Sherman, D., Cook, J. M. & Monte, A. (2008). Bioorg. Med. Chem. Lett. 18, 5745-5749.]); Lu et al. (2012[Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.]); Pavan et al. (2011[Pavan, F. R., de Carvalho, G. S. G., da Silva, A. D. & Leite, C. Q. F. (2011). Sci. World J. 11, 1113-1119.]). For related structures, see: Sun et al. (2011[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.]); Wang (2009[Wang, C.-Y. (2009). Acta Cryst. E65, o741.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO2

  • Mr = 241.28

  • Orthorhombic, P n a 21

  • a = 18.6882 (11) Å

  • b = 10.7420 (6) Å

  • c = 6.3186 (4) Å

  • V = 1268.45 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.59 × 0.27 × 0.25 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.979

  • 16922 measured reflections

  • 2382 independent reflections

  • 2319 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.086

  • S = 1.10

  • 2382 reflections

  • 168 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
O2-H1O2...N1i 0.83 (2) 1.87 (2) 2.6971 (12) 172 (2)
C6-H6A...O2ii 0.95 2.51 3.3956 (14) 156
C9-H9A...O2iii 0.95 2.38 3.3229 (13) 171
C14-H14B...Cg1iv 0.99 2.90 3.7668 (12) 147
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+2, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: RZ5061 ).


Acknowledgements

NK thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors extend their appreciation to the Malaysian Government and Universiti Sains Malaysia for APEX DE2012 grant No. 1002/PFIZIK/910323, and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, L.-X., Tang, J.-J., Luo, H., Jin, X.-L., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. & Zhou, B. (2010). Bioorg. Med. Chem. Lett. 20, 2417-2420.  [CrossRef] [ChemPort] [PubMed]
Kabir, M. S., Engelbrecht, K., Polanowski, R., Krueger, S. M., Ignasiak, R., Rott, M., Schwan, W. R., Stemper, M. E., Reed, K. D., Sherman, D., Cook, J. M. & Monte, A. (2008). Bioorg. Med. Chem. Lett. 18, 5745-5749.  [CrossRef] [PubMed] [ChemPort]
Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.  [CrossRef] [ChemPort] [PubMed]
Pavan, F. R., de Carvalho, G. S. G., da Silva, A. D. & Leite, C. Q. F. (2011). Sci. World J. 11, 1113-1119.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Silva, C. M. da, da Silva, D. L., Martins, C. V. B., de Resende, M. A., Dias, E. S., Magalhaes, T. F. F., Rodrigues, L. P., Sabino, A. A., Alves, R. B. & de Fatima, A. (2011). Chem. Biol. Drug Des. 78, 810-815.  [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.  [CSD] [CrossRef] [details]
Wang, C.-Y. (2009). Acta Cryst. E65, o741.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o903-o904   [ doi:10.1107/S1600536813012580 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.