[Journal logo]

Volume 70 
Part 1 
Pages o62-o63  
January 2014  

Received 29 November 2013
Accepted 5 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.148
Data-to-parameter ratio = 20.7
Details
Open access

(E)-2-[(2,4,6-Tri­meth­oxy­benzyl­idene)amino]­phenol1

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

There are two independent mol­ecules in the asymmetric unit of the title compound, C16H17NO4, with similar conformations but some differences in their bond angles. Each mol­ecule adopts a trans configuration with respect to the methyl­idene C=N bond and is twisted with a dihedral angle between the two substituted benzene rings of 80.52 (7)° in one mol­ecule and 83.53 (7)° in the other. All meth­oxy groups are approximately coplanar with the attached benzene rings, with Cmeth­yl-O-C-C torsion angles ranging from -6.7 (2) to 5.07 (19)°. In the crystal, independent mol­ecules are linked together by O-H...N and O-H...O hydrogen bonds and a [pi]-[pi] inter­action [centroid-centroid distance of 3.6030 (9) Å], forming a dimer. The dimers are further linked by weak C-H...O inter­actions and another [pi]-[pi] inter­action [centroid-centroid distance of 3.9452 (9) Å] into layers lying parallel to the ab plane.

Related literature

For organic bond-length data, 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. S1-19.]). For related literature on 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 background to and application 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.]); Fujita et al. (2012[Fujita, Y., Islam, R., Sakai, K., Kaneda, H., Kudo, K., Tamura, D., Aomatsu, K., Nagai, T., Kimura, H., Matsumoto, K., de Velasco, M. A., Arao, T., Okawara, T. & Nishio, K. (2012). Invest. New Drugs, 30, 1878-1886.]); 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.]); Tamizh et al. (2012[Tamizh, M. M., Kesavan, D., Sivakumar, P. M., Mereiter, K., Deepa, M., Kirchner, K., Doble, M. & Karvembu, R. (2012). Chem. Biol. Drug Des. 79, 177-185.]). For related structures, see: Kaewmanee et al. (2013[Kaewmanee, N., Chantrapromma, S., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o903-o904.]); Sun et al. (2011[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17NO4

  • Mr = 287.31

  • Triclinic, [P \overline 1]

  • a = 7.3819 (6) Å

  • b = 11.7036 (9) Å

  • c = 16.4373 (13) Å

  • [alpha] = 89.469 (2)°

  • [beta] = 85.616 (2)°

  • [gamma] = 80.456 (2)°

  • V = 1396.34 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.49 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX2 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.985

  • 29313 measured reflections

  • 8129 independent reflections

  • 5872 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.148

  • S = 1.02

  • 8129 reflections

  • 393 parameters

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

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4A-H1O4...O3B 0.88 (2) 2.53 (2) 2.9924 (15) 114.0 (17)
O4A-H1O4...N1B 0.88 (2) 1.96 (2) 2.7897 (15) 158 (2)
O4B-H2O4...N1A 0.88 (2) 2.00 (2) 2.8013 (16) 151 (2)
O4B-H2O4...N1B 0.88 (2) 2.35 (2) 2.7891 (16) 111.1 (18)
C13B-H13B...O3Ai 0.95 2.59 3.4639 (19) 154
C15B-H15D...O4Aii 0.98 2.43 3.3847 (18) 164
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z.

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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5324 ).


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. S1-19.  [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
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]
Fujita, Y., Islam, R., Sakai, K., Kaneda, H., Kudo, K., Tamura, D., Aomatsu, K., Nagai, T., Kimura, H., Matsumoto, K., de Velasco, M. A., Arao, T., Okawara, T. & Nishio, K. (2012). Invest. New Drugs, 30, 1878-1886.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Kaewmanee, N., Chantrapromma, S., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o903-o904.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.  [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.  [CSD] [CrossRef] [IUCr Journals]
Tamizh, M. M., Kesavan, D., Sivakumar, P. M., Mereiter, K., Deepa, M., Kirchner, K., Doble, M. & Karvembu, R. (2012). Chem. Biol. Drug Des. 79, 177-185.  [CSD] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o62-o63   [ doi:10.1107/S1600536813032996 ]

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.