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

Praveen, A.S.; Jasinski, J.P.; Keeley, A.C.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536812047113

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 (C-C) = 0.003 Å
R = 0.052
wR = 0.158
Data-to-parameter ratio = 14.7
Details

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

A. S. Praveen,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b H. S. Yathirajan ^a and B. Narayana ^c

^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-HO 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); El-Masry et al. (2000); Hodnett & Dunn (1970); Pandey et al. (1999); Singh & Dash (1988). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002). For related structures, see: Akkurt et al. (2011); Lv et al. (2009a,b); Yu & Lv (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₈N₂O₂
M_r = 282.33
Triclinic, $[P \overline 1]$
a = 6.4961 (8) Å
b = 9.8047 (10) Å
c = 12.7464 (13) Å
= 112.130 (9)°
= 95.507 (10)°
= 96.601 (9)°
V = 738.45 (14) Å³
Z = 2
Cu K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.735, T_max = 1.000
4418 measured reflections
2840 independent reflections
2032 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.158
S = 1.04
2840 reflections
193 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3-C8 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.04	2.902 (2)	178
C15-H15Cgⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.
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.
Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009a). Acta Cryst. E65, o1990.
Lv, L.-P., Yu, T.-M., Yu, W.-B., Li, W.-W. & Hu, X.-C. (2009b). Acta Cryst. E65, o1989.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Yu, T.-M. & Lv, L.-P. (2010). Acta Cryst. E66, o2666.

organic compounds