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Volume 69 
Part 11 
Page o1607  
November 2013  

Received 20 September 2013
Accepted 30 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.147
Data-to-parameter ratio = 11.3
Details
Open access

Dimethyl 4,4'-(diazenedi­yl)dibenzoate at 100 K

aFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland
Correspondence e-mail: eismont@uni.opole.pl

In the asymmetric part of the unit cell of the title compound, C16H14N2O4, there are two chemically equivalent but crystallographic independent half mol­ecules. The geometric centre of each complete mol­ecule lies on a crystallographic inversion centre. Both mol­ecules are almost planar [mean deviations of atoms in the two molecules are 0.032 (2) and 0.044 (2) Å] and their geometries are similar. In the crystal, mol­ecules are arranged in columns along the a axis. There are no inter­molecular donor-acceptor distances shorter than 3.4 Å.

Related literature

For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Allmann (1997[Allmann, R. (1997). The Chemistry of the Hydrazo, Azo and Azoxy groups, Vol. 2, edited by S. Patai, pp. 23-52. New York: John Wiley & Sons.]); Scott et al., (2002[Scott, J., Asami, M. & Tanaka, K. (2002). New J. Chem. 26, 1822-1826.]); Maniam et al. (2008[Maniam, S., Cieslinski, M. M., Lincoln, S. F., Onagi, H., Steel, P. J., Willis, A. C. & Easton, C. J. (2008). Org. Lett. 10, 1885-1888.]); Zeitouny et al., (2009[Zeitouny, J., Aurisicchio, C., Bonifazi, D., De Zorzi, R., Geremia, S., Bonini, M., Palma, C.-A., Samori, P., Listorti, A., Belbakra, A. & Armaroli, N. (2009). J. Mater. Chem. 19, 4715-4724.]). For a related structure, see: Yu & Liu (2009[Yu, Q.-D. & Liu, Y.-Y. (2009). Acta Cryst. E65, o2326.]); Niu et al. (2011[Niu, Y., Huang, J., Zhao, C., Gao, P. & Yu, Y. (2011). Acta Cryst. E67, o2671.]). For related literature, see: Onto et al. (1998[Onto, K., Hatakeyama, T., Takeo, M., Uchiito, S., Tokuda, M. & Suginome, H. (1998). Tetrahedron, 54, 8403-8410.]). For the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O4

  • Mr = 298.29

  • Triclinic, [P \overline 1]

  • a = 3.8146 (8) Å

  • b = 11.2571 (18) Å

  • c = 16.904 (3) Å

  • [alpha] = 72.456 (16)°

  • [beta] = 85.030 (18)°

  • [gamma] = 84.468 (16)°

  • V = 687.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.35 × 0.17 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • 4264 measured reflections

  • 2405 independent reflections

  • 1652 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.147

  • S = 1.05

  • 2405 reflections

  • 213 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2074 ).


References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Allmann, R. (1997). The Chemistry of the Hydrazo, Azo and Azoxy groups, Vol. 2, edited by S. Patai, pp. 23-52. New York: John Wiley & Sons.
Maniam, S., Cieslinski, M. M., Lincoln, S. F., Onagi, H., Steel, P. J., Willis, A. C. & Easton, C. J. (2008). Org. Lett. 10, 1885-1888.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Niu, Y., Huang, J., Zhao, C., Gao, P. & Yu, Y. (2011). Acta Cryst. E67, o2671.  [CSD] [CrossRef] [IUCr Journals]
Onto, K., Hatakeyama, T., Takeo, M., Uchiito, S., Tokuda, M. & Suginome, H. (1998). Tetrahedron, 54, 8403-8410.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Scott, J., Asami, M. & Tanaka, K. (2002). New J. Chem. 26, 1822-1826.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yu, Q.-D. & Liu, Y.-Y. (2009). Acta Cryst. E65, o2326.  [CSD] [CrossRef] [IUCr Journals]
Zeitouny, J., Aurisicchio, C., Bonifazi, D., De Zorzi, R., Geremia, S., Bonini, M., Palma, C.-A., Samori, P., Listorti, A., Belbakra, A. & Armaroli, N. (2009). J. Mater. Chem. 19, 4715-4724.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1607  [ doi:10.1107/S1600536813026846 ]

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