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Volume 69 
Part 11 
Page o1614  
November 2013  

Received 30 September 2013
Accepted 1 October 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.128
Data-to-parameter ratio = 18.2
Details
Open access

N'-[(E)-Benzyl­idene]-2-(6-meth­oxy­naphthalen-2-yl)propano­hydrazide

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt,eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The title mol­ecule, C21H20N2O2, exists in the solid state in the `extended' form. The crystal packing consists of ribbons of mol­ecules extending parallel to c and associated via N-H...O and weak C-H...O hydrogen bonds. C-H...[pi] inter­actions are also present.

Related literature

For general clinical use of nonsteroidal anti-inflammatory drugs (NSAIDs) and Naproxen®, see: Merlet et al. (2013[Merlet, N., Busseuil, D., Rhéaume, E. & Tardif, J.-C. (2013). Anti-Inflammatory Anti-Allergy Agents Med. Chem. 12, 24-35.]); Khanna et al. (2006[Khanna, S., Madan, M., Vangoori, A., Banerjee, R., Thaimattam, R., Sadik, J., Basha, S. K., Ramesh, M., Casturi, S. R. & Pal, M. (2006). Bioorg. Med. Chem. 14, 4820-4833.]); Bhaduri et al. (1995[Bhaduri, J., Hota, D. & Acharya, S. B. (1995). Indian J. Exp. Biol. 33, 667-681.]); Dharmani et al. (2004[Dharmani, P., Kuchibhotla, V. K., Maurya, R., Srivatsava, S., Sharma, S. & Palit, G. (2004). J. Ethnopharmacol. 93, 197-206.]). For common side effects of NSAIDs, see: Neeraj et al. (2010[Neeraj, A., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Delivery Technol. 2, 12-17.]); Asif (2009[Asif, H. (2009). Acta Pol. Pharm. Drug Res. 66, 513-521.]); Parmeshwari et al. (2009[Parmeshwari, K. H., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20N2O2

  • Mr = 332.39

  • Orthorhombic, P 21 21 21

  • a = 10.3754 (17) Å

  • b = 32.519 (5) Å

  • c = 5.0615 (8) Å

  • V = 1707.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.15 × 0.11 × 0.11 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 = 0.73, Tmax = 0.99

  • 28152 measured reflections

  • 4230 independent reflections

  • 3882 reflections with I > 2[sigma](I)

  • Rint = 0.053

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

  • wR(F2) = 0.128

  • S = 1.10

  • 4230 reflections

  • 232 parameters

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4-C9 benzene and C16-C21 phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.94 (3) 1.98 (4) 2.892 (3) 163 (3)
C15-H15...O2i 0.95 2.49 3.261 (3) 138
C18-H18...O1ii 0.95 2.59 3.209 (4) 123
C1-H1C...Cg3iii 0.98 2.91 3.696 (3) 138
C12-H12...Cg2i 1.00 2.78 3.661 (3) 147
Symmetry codes: (i) x, y, z-1; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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.]); software used to prepare material for publication: WinGX (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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5356 ).


Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University and Erciyes University for supporting this study.

References

Asif, H. (2009). Acta Pol. Pharm. Drug Res. 66, 513-521.
Bhaduri, J., Hota, D. & Acharya, S. B. (1995). Indian J. Exp. Biol. 33, 667-681.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dharmani, P., Kuchibhotla, V. K., Maurya, R., Srivatsava, S., Sharma, S. & Palit, G. (2004). J. Ethnopharmacol. 93, 197-206.  [Web of Science] [CrossRef] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Khanna, S., Madan, M., Vangoori, A., Banerjee, R., Thaimattam, R., Sadik, J., Basha, S. K., Ramesh, M., Casturi, S. R. & Pal, M. (2006). Bioorg. Med. Chem. 14, 4820-4833.  [CrossRef] [PubMed] [ChemPort]
Merlet, N., Busseuil, D., Rhéaume, E. & Tardif, J.-C. (2013). Anti-Inflammatory Anti-Allergy Agents Med. Chem. 12, 24-35.  [CrossRef] [ChemPort]
Neeraj, A., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Delivery Technol. 2, 12-17.
Parmeshwari, K. H., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1614  [ doi:10.1107/S1600536813026986 ]

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