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Volume 69 
Part 7 
Page o1039  
July 2013  

Received 21 May 2013
Accepted 24 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.079
Data-to-parameter ratio = 13.7
Details
Open access

(E)-1-(2,4-Dinitrobenzylidene)-2,2-diphenylhydrazine

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

In the crystal of the title compound, C19H14N4O4, the asymmetric unit consists of two discrete molecules. The C=N bonds in both molecules show an E conformation. The dihedral angles between the C atoms of the 2,4-dinitrobenzene rings and the C=N-N planes are 13.52 (9) and 13.82 (9)° for the two molecules. In the crystal, C-H...O hydrogen bonds, mainly between the phenyl ring and the nitro group along the b axis.

Related literature

For the synthesis and related structures, see: Vicini et al. (2002[Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.]); Rollas et al. (2002[Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.]); Mendoza et al. (2012[Mendoza, A., Meléndrez-Luevano, R., Cabrera-Vivas, B. M., Acoltzi-X, C. & Flores-Alamo, M. (2012). Acta Cryst. E68, o3238.]). For applications of hydrazones, see: Angell et al. (2006[Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. (2006). Coord. Chem. Rev. 250, 1829-1841.]); Clulow et al. (2008[Clulow, A. J., Selby, J. D., Cushion, M. G., Schwarz, A. D. & Mountford, P. (2008). Inorg. Chem. 47, 12049-12062.]); Motherwell & Ramsay (2007[Motherwell, W. D. S. & Ramsay, J. (2007). Acta Cryst. E63, o4043.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N4O4

  • Mr = 362.34

  • Triclinic, [P \overline 1]

  • a = 7.0288 (6) Å

  • b = 13.5001 (7) Å

  • c = 17.9271 (11) Å

  • [alpha] = 91.878 (5)°

  • [beta] = 93.431 (6)°

  • [gamma] = 91.548 (6)°

  • V = 1696.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.59 × 0.38 × 0.12 mm

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

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.955, Tmax = 0.988

  • 13303 measured reflections

  • 6694 independent reflections

  • 3465 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.079

  • S = 1.01

  • 6694 reflections

  • 487 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11A-H11A...O2Ai 0.93 2.59 3.306 (2) 134
C11B-H11B...O2Bi 0.93 2.72 3.370 (2) 128
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: BT6909 ).


Acknowledgements

The authors are grateful for financial support (project No. CAVB-NAT13-G). MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. (2006). Coord. Chem. Rev. 250, 1829-1841.  [Web of Science] [CrossRef] [ChemPort]
Clulow, A. J., Selby, J. D., Cushion, M. G., Schwarz, A. D. & Mountford, P. (2008). Inorg. Chem. 47, 12049-12062.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mendoza, A., Meléndrez-Luevano, R., Cabrera-Vivas, B. M., Acoltzi-X, C. & Flores-Alamo, M. (2012). Acta Cryst. E68, o3238.  [CSD] [CrossRef] [IUCr Journals]
Motherwell, W. D. S. & Ramsay, J. (2007). Acta Cryst. E63, o4043.  [CSD] [CrossRef] [IUCr Journals]
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1039  [ doi:10.1107/S1600536813014360 ]

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