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Volume 69 
Part 1 
Page o90  
January 2013  

Received 6 December 2012
Accepted 9 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 13.0
Details
Open access

1-{(E)-[5-(2-Nitrophenyl)furan-2-yl]methylidene}-2,2-diphenylhydrazine

aFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico, and bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico
Correspondence e-mail: mfa@unam.mx

In the title compound, C23H17N3O3, the terminal benzene rings are oriented at dihedral angles of 3.67 (7), 76.02 (7) and 16.37 (7)° with respect to the central furan ring. In the crystal, molecules are connected via weak C-H...O hydrogen bonds, resulting in a three-dimensional supramolecular array.

Related literature

For applications of hydrazones, see: Robinson (1963[Robinson, B. (1963). Chem. Rev. 63, 373-382.]); Sztanke et al. (2007[Sztanke, K., Pasterhak, K., Rzymowska, J., Sztanke, M. & Kandefer-Szerszen, M. (2007). Eur. J. Med. Chem. 43, 404-419.]); Al-Macrosaur et al. (2007[Al-Macrosaur, L. Q., Dayam, R., Taheri, L., Witvrouw, M., Debyser, Z. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6472-6475.]); Kucukguzel et al. (2003[Kucukguzel, S. G., Mazi, A., Sahin, F., Ozturk, S. & Stables, J. (2003). Eur. J. Med. Chem. 38, 1005-1013.]); Roma et al. (2000[Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1035.]); Smalley et al. (2006[Smalley, T. L. Jr, Peat, A. J., Boucheron, J. A., Dickerson, S., Garrido, D., Preugschat, F., Schweiker, S. L., Thomson, S. A. & Wang, T. Y. (2006). Bioorg. Med. Chem. Lett. 16, 2091-2094.]); Gemma et al. (2006[Gemma, S., Kukreja, G., Fattorusso, C., Persico, M., Romano, M. P., Altarelli, M., Savini, L., Campiani, G., Fattorusso, E., Basilico, N., Taramelli, D., Yardley, V. & Butini, S. (2006). Bioorg. Med. Chem. Lett. 6, 5384-5388.]). 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
  • C23H17N3O3

  • Mr = 383.4

  • Monoclinic, C 2/c

  • a = 11.2439 (2) Å

  • b = 17.3325 (4) Å

  • c = 19.7575 (4) Å

  • [beta] = 105.778 (2)°

  • V = 3705.36 (13) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.76 mm-1

  • T = 130 K

  • 0.58 × 0.23 × 0.16 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.759, Tmax = 0.892

  • 12881 measured reflections

  • 3395 independent reflections

  • 3070 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.03

  • 3395 reflections

  • 262 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O2i 0.95 2.48 3.1294 (16) 126
C11-H11...O3ii 0.95 2.57 3.4336 (18) 151
C12-H12...O3iii 0.95 2.48 3.3786 (18) 158
Symmetry codes: (i) x+1, y, z; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5663 ).


Acknowledgements

We are grateful for financial support (project No. CAVB-NATG-12, VIEP-BUAP). MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

Al-Macrosaur, L. Q., Dayam, R., Taheri, L., Witvrouw, M., Debyser, Z. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6472-6475.  [PubMed]
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]
Gemma, S., Kukreja, G., Fattorusso, C., Persico, M., Romano, M. P., Altarelli, M., Savini, L., Campiani, G., Fattorusso, E., Basilico, N., Taramelli, D., Yardley, V. & Butini, S. (2006). Bioorg. Med. Chem. Lett. 6, 5384-5388.  [CrossRef]
Kucukguzel, S. G., Mazi, A., Sahin, F., Ozturk, S. & Stables, J. (2003). Eur. J. Med. Chem. 38, 1005-1013.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Robinson, B. (1963). Chem. Rev. 63, 373-382.  [CrossRef] [ISI]
Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1035.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smalley, T. L. Jr, Peat, A. J., Boucheron, J. A., Dickerson, S., Garrido, D., Preugschat, F., Schweiker, S. L., Thomson, S. A. & Wang, T. Y. (2006). Bioorg. Med. Chem. Lett. 16, 2091-2094.  [CrossRef] [PubMed] [ChemPort]
Sztanke, K., Pasterhak, K., Rzymowska, J., Sztanke, M. & Kandefer-Szerszen, M. (2007). Eur. J. Med. Chem. 43, 404-419.  [ISI] [CrossRef] [PubMed]


Acta Cryst (2013). E69, o90  [ doi:10.1107/S1600536812050246 ]

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