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Volume 69 
Part 11 
Pages o1660-o1661  
November 2013  

Received 30 September 2013
Accepted 2 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.090
Data-to-parameter ratio = 12.7
Details
Open access

N'-[(E)-4-Meth­oxy­benzyl­idene]-2-(5-meth­oxy-2-methyl-1H-indol-3-yl)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, 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 conformation adopted by the title compound, C20H21N3O3, in the crystal is `J'-shaped and 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, forming dimers with R22(8) motifs. Furthermore, these dimers connect to each other via C-H...O and N-H...O hydrogen bonds to form a three-dimensional network.

Related literature

For general medical applications of non-steriodal anti-inflammatory drugs (NSAIDs), see: Richy et al. (2004[Richy, F., Bruyere, O., Ethgen, O., Rabenda, V., Bouvenot, G., Audran, M., Herrero-Beaumont, G., Moore, A., Eliakim, R., Haim, M. & Reginster, J.-Y. (2004). Ann. Rheum. Dis. 63, 759-766.]). For the undesirable side effects of such drugs, see: Allison et al. (1992[Allison, M. C., Howatson, A. G., Torrance, C. J., Lee, F. D. & Russell, R. I. (1992). N. Engl. J. Med. 327, 749-754.]); McMahon (2001[McMahon, A. D. (2001). Am. J. Epidemiol. 154, 557-562.]); Rocha et al. (2001[Rocha, G. M., Michea, L. F., Peters, E. M., Kirby, M., Xu, Y., Ferguson, D. R. & Burg, M. B. (2001). Proc. Natl Acad. Sci. USA, 98, 5317-5322.]); Halen et al. (2009[Halen, P. K., Prashant, R., Murumkar, P. R., Giridhar, R. & Mange Ram Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.]). For a similar structure, see: Mague et al. (2013[Mague, J. T., Akkurt, M., Mohamed, S. K., El-Remaily, M. A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1614.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21N3O3

  • Mr = 351.40

  • Triclinic, [P \overline 1]

  • a = 7.1894 (2) Å

  • b = 10.4055 (3) Å

  • c = 12.4403 (4) Å

  • [alpha] = 107.983 (2)°

  • [beta] = 92.451 (2)°

  • [gamma] = 97.882 (2)°

  • V = 873.24 (5) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 100 K

  • 0.14 × 0.12 × 0.08 mm

Data collection
  • Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.85, Tmax = 0.94

  • 8928 measured reflections

  • 3121 independent reflections

  • 2579 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.090

  • S = 1.04

  • 3121 reflections

  • 246 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.88 (2) 2.04 (2) 2.9212 (17) 174.0 (18)
N2-H2...O2ii 0.920 (18) 1.988 (18) 2.9025 (16) 171.9 (15)
C4-H4...O3iii 0.95 2.50 3.410 (2) 161
C11-H11B...N3 0.99 2.36 2.8373 (19) 109
C20-H20A...O1iv 0.98 2.49 3.215 (2) 131
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y+2, -z+2; (iii) x+1, y-1, z; (iv) x-1, y, z.

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: SJ5357 ).


Acknowledgements

The authors are deeply grateful to Tulane University, Erciyes University and Manchester Metropolitan University for supporting this study.

References

Allison, M. C., Howatson, A. G., Torrance, C. J., Lee, F. D. & Russell, R. I. (1992). N. Engl. J. Med. 327, 749-754.  [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Halen, P. K., Prashant, R., Murumkar, P. R., Giridhar, R. & Mange Ram Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.  [CrossRef] [PubMed] [ChemPort]
Mague, J. T., Akkurt, M., Mohamed, S. K., El-Remaily, M. A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1614.  [CSD] [CrossRef] [IUCr Journals]
McMahon, A. D. (2001). Am. J. Epidemiol. 154, 557-562.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Richy, F., Bruyere, O., Ethgen, O., Rabenda, V., Bouvenot, G., Audran, M., Herrero-Beaumont, G., Moore, A., Eliakim, R., Haim, M. & Reginster, J.-Y. (2004). Ann. Rheum. Dis. 63, 759-766.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rocha, G. M., Michea, L. F., Peters, E. M., Kirby, M., Xu, Y., Ferguson, D. R. & Burg, M. B. (2001). Proc. Natl Acad. Sci. USA, 98, 5317-5322.  [CrossRef] [PubMed] [ChemPort]
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, o1660-o1661   [ doi:10.1107/S1600536813027050 ]

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