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Volume 69 
Part 3 
Page o400  
March 2013  

Received 11 February 2013
Accepted 14 February 2013
Online 20 February 2013

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Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.080
Data-to-parameter ratio = 13.6
Details
Open access

(E)-2,4-Dimethyl-N'-(2-methylbenzylidene)benzohydrazide

Muhammad Taha,a Nor Hadiani Ismail,b Faridahanim Mohd Jaafar,b Khalid M. Khanc and Sammer Yousufc*

aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia,bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Malaysia, and cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title benzoylhydrazide derivative, C17H18N2O, the dihedral angle between the benzene rings is 88.45 (8)° and the azomethine double bond adopts an E conformation. In the crystal, molecules are linked by N-H...O and C-H...O hydrogen bonds, forming a chain along the b axis.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012[Musharraf, S. G., Bibi, A., Shahid, N., Najam-ul-Haq, M., Khan, M., Taha, M., Mughal, U. R. & Khan, K. M. (2012). Am. J. Anal. Chem. 3, 779-789.]); Khan et al. (2012[Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.]). For the crystal structures of related compounds, see: Taha et al. (2012a[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012a). Acta Cryst. E68, o2778.],b[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012b). Acta Cryst. E68, o2780.]); Naz et al. (2012[Naz, H., Taha, M., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2671.]).

[Scheme 1]

Experimental

Crystal data

  • C17H18N2O

  • Mr = 266.33

  • Orthorhombic, P c a 21

  • a = 26.1151 (10) Å

  • b = 4.9484 (2) Å

  • c = 11.3933 (4) Å

  • V = 1472.33 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 273 K

  • 0.56 × 0.55 × 0.23 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.983

  • 8023 measured reflections

  • 2577 independent reflections

  • 2483 reflections with I > 2[sigma](I)

  • Rint = 0.021
Refinement

  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.080

  • S = 1.04

  • 2577 reflections

  • 189 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.833 (15) 2.000 (15) 2.8150 (14) 166.1 (14)
C8-H8A...O1i 0.93 2.52 3.2696 (19) 138
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: IS5246 ).

Acknowledgements

The authors would like to acknowledge the Research Management Institute of UiTM for financial support under the Dana Kecemerlangan Grant Scheme [grant No. 600-RMI/DANA 5/3 RIF (143/2012)].

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.  [ChemPort] [PubMed]
Musharraf, S. G., Bibi, A., Shahid, N., Najam-ul-Haq, M., Khan, M., Taha, M., Mughal, U. R. & Khan, K. M. (2012). Am. J. Anal. Chem. 3, 779-789.  [CrossRef]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Naz, H., Taha, M., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2671.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012a). Acta Cryst. E68, o2778.  [CSD] [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012b). Acta Cryst. E68, o2780.  [CSD] [CrossRef] [details]

Acta Cryst (2013). E69, o400  [ doi:10.1107/S1600536813004388 ]

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