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Volume 68 
Part 11 
Page o3238  
November 2012  

Received 17 October 2012
Accepted 22 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 14.8
Details
Open access

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

aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico,bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and cFacultad de Química, Universidad Nacional Autónoma de México, 04510, México D.F., Mexico
Correspondence e-mail: angel.mendoza.m@gmail.com

The asymmetric unit of the title compound, C19H15N3O2, contains two molecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenylhydrazine groups are 86.09 (6) and 83.41 (5)° in the two molecules. The 4-nitrobenzene rings show torsion angles of 4.4 (2) and 10.9 (2)° from the two C=N-N planes. In the crystal, C-H...[pi] interactions and C-H...O hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.

Related literature

For applications of hydrazones, see: Angell et al. (2006[Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829-1841.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O2

  • Mr = 317.34

  • Triclinic, [P \overline 1]

  • a = 10.8648 (6) Å

  • b = 11.1477 (6) Å

  • c = 16.2075 (7) Å

  • [alpha] = 72.084 (4)°

  • [beta] = 89.037 (4)°

  • [gamma] = 62.084 (6)°

  • V = 1631.47 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.6 × 0.36 × 0.29 mm

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

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.963, Tmax = 0.98

  • 11850 measured reflections

  • 6432 independent reflections

  • 3566 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.100

  • S = 0.89

  • 6432 reflections

  • 434 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21-C26, C33-C38 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3...Cg1i 0.93 2.92 3.4080 (18) 114
C29-H29...Cg2ii 0.93 2.80 3.6875 (18) 161
C7-H7...Cg2 0.93 2.83 3.4223 (16) 123
C30-H30...Cg3iii 0.93 2.84 3.698 (2) 154
C6-H6...O2iv 0.93 2.60 3.342 (3) 138
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y+2, -z; (iv) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6850 ).


Acknowledgements

We are grateful for financial support (project No. CAVB-NAT11-I, VIEP-BUAP).

References

Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829-1841.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, 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] [details]
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3238  [ doi:10.1107/S1600536812043681 ]

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