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Volume 69 
Part 9 
Page o1493  
September 2013  

Received 16 August 2013
Accepted 23 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.126
Data-to-parameter ratio = 18.7
Details
Open access

2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N'-[(1E,2E)-3-phenylprop-2-en-1-ylidene]acetohydrazide

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq,fDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada E-18071, Spain, and gDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C21H21N3O2, adopts a J-shaped conformation which appears to be at least partially directed by a weak intramolecular C-H...N hydrogen bond. In the crystal, molecules are linked by N-H...O hydrogen bonds into R22(8) and R22(14) cyclic dimers, which form a chain running parallel to the b axis.

Related literature

For general background to side-effect toxicity of non-steroidal anti-inflammatory drugs (NSAIDs), see: Agrawal et al. (2010[Agrawal, N., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Tech. 2, 12-17.]); Champion et al. (1997[Champion, G. D., Feng, P. H., Azuma, T., Caughey, D. E., Chan, K. H., Kashiwazaki, S., Liu, H.-C., Nasution, A. R., Hobunaga, M., Prichanond, S., Torralba, T. P., Udom, V. & Yoo, M. C. (1997). Drugs, 53, 61-69.]); Allan & Fletcher (1990[Allan, H. P. & Fletcher, M. (1990). Drugs, 40, 1-11.]). For reduction of GI toxicity attributed to NSAIDs, see: Halen et al. (2009[Halen, P. K., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.]); Schoen & Vender (1989[Schoen, R. T. & Vender, R. J. (1989). Am. J. Med. 86, 449-458.]); Mitchell & Warner (1999[Mitchell, J. A. & Warner, T. D. (1999). Br. J. Pharmacol. 128, 1121-1132.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21N3O2

  • Mr = 347.41

  • Triclinic, [P \overline 1]

  • a = 8.2786 (9) Å

  • b = 10.1194 (11) Å

  • c = 11.7739 (13) Å

  • [alpha] = 93.001 (2)°

  • [beta] = 108.993 (2)°

  • [gamma] = 105.578 (2)°

  • V = 887.76 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.26 × 0.13 × 0.08 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.78, Tmax = 0.99

  • 16303 measured reflections

  • 4574 independent reflections

  • 3675 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.126

  • S = 1.08

  • 4574 reflections

  • 245 parameters

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.891 (18) 2.093 (18) 2.9841 (14) 178.1 (9)
N2-H2...O2ii 0.903 (16) 2.012 (16) 2.9055 (13) 170.0 (14)
C7-H7...N3 0.95 2.54 3.3609 (15) 145
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2100 ).


Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

References

Agrawal, N., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Tech. 2, 12-17.
Allan, H. P. & Fletcher, M. (1990). Drugs, 40, 1-11.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Champion, G. D., Feng, P. H., Azuma, T., Caughey, D. E., Chan, K. H., Kashiwazaki, S., Liu, H.-C., Nasution, A. R., Hobunaga, M., Prichanond, S., Torralba, T. P., Udom, V. & Yoo, M. C. (1997). Drugs, 53, 61-69.  [CrossRef]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Halen, P. K., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.  [CrossRef] [PubMed] [ChemPort]
Mitchell, J. A. & Warner, T. D. (1999). Br. J. Pharmacol. 128, 1121-1132.  [CrossRef] [PubMed] [ChemPort]
Schoen, R. T. & Vender, R. J. (1989). Am. J. Med. 86, 449-458.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1493  [ doi:10.1107/S1600536813023805 ]

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