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Volume 68 
Part 12 
Page o3435  
December 2012  

Received 12 November 2012
Accepted 15 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.158
Data-to-parameter ratio = 14.7
Details
Open access

(E)-N'-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title molecule, C17H18N2O2, the benzene rings form a dihedral angle of 83.0 (7)°. In the crystal, N-H...O hydrogen bonds, in an R22(8) graph-set motif, link molecules into centrocymmetric dimers, and weak C-H...[pi] interactions further link these dimers into columns in [100].

Related literature

For the biological activity of Schiff bases, see: Desai et al. (2001[Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.]); El-Masry et al. (2000[El-Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.]); Hodnett & Dunn (1970[Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768-770.]); Pandey et al. (1999[Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Il Farmaco, 54, 624-628.]); Singh & Dash (1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001[Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002[Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.]). For related structures, see: Akkurt et al. (2011[Akkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184-o185.]); Lv et al. (2009a[Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009a). Acta Cryst. E65, o1990.],b[Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009b). Acta Cryst. E65, o1989.]); Yu & Lv (2010[Yu, T.-M. & Lv, L.-P. (2010). Acta Cryst. E66, o2666.]). 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. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N2O2

  • Mr = 282.33

  • Triclinic, [P \overline 1]

  • a = 6.4961 (8) Å

  • b = 9.8047 (10) Å

  • c = 12.7464 (13) Å

  • [alpha] = 112.130 (9)°

  • [beta] = 95.507 (10)°

  • [gamma] = 96.601 (9)°

  • V = 738.45 (14) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.68 mm-1

  • T = 173 K

  • 0.34 × 0.14 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.735, Tmax = 1.000

  • 4418 measured reflections

  • 2840 independent reflections

  • 2032 reflections with I > 2[sigma](I)

  • Rint = 0.034

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

  • wR(F2) = 0.158

  • S = 1.04

  • 2840 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3-C8 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.04 2.902 (2) 178
C15-H15...Cgii 0.93 2.63 3.557 (2) 173
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5364 ).


Acknowledgements

ASP thanks UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Akkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184-o185.  [CrossRef] [details]
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.
Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.  [ChemPort]
Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.  [CrossRef] [ChemPort]
El-Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768-770.  [CrossRef] [ChemPort] [PubMed] [ISI]
Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009a). Acta Cryst. E65, o1990.  [CSD] [CrossRef] [details]
Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009b). Acta Cryst. E65, o1989.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Il Farmaco, 54, 624-628.  [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yu, T.-M. & Lv, L.-P. (2010). Acta Cryst. E66, o2666.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3435  [ doi:10.1107/S1600536812047113 ]

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