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Volume 69 
Part 5 
Page o705  
May 2013  

Received 15 February 2013
Accepted 4 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.074
wR = 0.242
Data-to-parameter ratio = 14.1
Details
Open access

1-[(E)-Anthracen-9-ylmethylidene]-2-(2,4-dinitrophenyl)hydrazine

aChemistry Department, University of Coimbra, P-3004-530 Coimbra, Portugal, and bCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal
Correspondence e-mail: xelo@teor.fis.uc.pt

In the title Schiff base, C21H14N4O4, the dihedral angle between the two nitro groups and the central benzene ring are 83.6 (5) and 2.6 (6)°. The anthracene ring system and the benzene ring make a dihedral angle of 0.7 (2)°. Intramolecular N-H...O and C-H...N hydrogen bonds occur. In the crystal, C-H...O hydrogen bonds link the molecules, forming chains along the b-axis direction.

Related literature

For general background to hydrazone derivatives, see: Kahwa et al. (1986[Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.]). For the structures of 2,4-dinitrophenylhydrazine and 9-anthraldehyde, see: Okabe et al. (1993[Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.]) and Trotter (1959[Trotter, J. (1959). Acta Cryst. 12, 922-928.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C21H14N4O4

  • Mr = 386.36

  • Orthorhombic, P 21 21 21

  • a = 5.6355 (4) Å

  • b = 8.1597 (5) Å

  • c = 36.794 (2) Å

  • V = 1691.95 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.08 × 0.02 × 0.01 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.764, Tmax = 0.999

  • 18174 measured reflections

  • 3708 independent reflections

  • 1466 reflections with I > 2[sigma](I)

  • Rint = 0.132

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.242

  • S = 0.88

  • 3708 reflections

  • 263 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H03...O4 0.86 1.99 2.617 (7) 129
C11-H11...O4i 0.93 2.47 3.251 (8) 142
C20-H20...N4 0.93 2.25 2.894 (8) 126
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Winsconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Winsconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX publication routines (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: BT6891 ).


Acknowledgements

This work was supported by the Fundo Europeu de Desenvolvimento Regional-QREN-Compete through projects SFRH/BD/61637/2009, PTDC/AAC-CLI/098308/2008, PTDC/AAC-CLI/118092/2010, PTDC/FIS/102284/2008 and PEst-C/FIS/UI0036/2011 - Fundação para a Ciência e Tecnologia (FCT).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Winsconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.  [CrossRef] [ChemPort] [ISI]
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.  [CrossRef] [details]
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Trotter, J. (1959). Acta Cryst. 12, 922-928.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o705  [ doi:10.1107/S1600536813009197 ]

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