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Volume 69 
Part 5 
Page o682  
May 2013  

Received 18 February 2013
Accepted 29 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.035
wR = 0.090
Data-to-parameter ratio = 6.4
Details
Open access

2-Methoxy-1-(2-methoxy-4-nitronaphthalen-1-yl)-6-nitronaphthalene

aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand,bSupramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand, and cDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand
Correspondence e-mail: , fscitwd@ku.ac.th

In the title compound, C22H16N2O6, the naphthalene ring systems form a dihedral angle of 65.2 (1)°. Two O atoms of one of the nitro groups are disordered over two sets of sites with occupancy factors of 0.586 (15) and 0.414 (15). Weak C-H...O intermolecular interactions are present, forming a ladder like structure along the a axis.

Related literature

For related structures, see: Thorup et al. (2006[Thorup, N., Deussen, H.-J., Bechgaard, K. & Bjørnholm, T. (2006). Acta Cryst. E62, o1342-o1343.],) ; Thoss et al. (2009[Thoss, M., Seidel, R. W. & Feigel, M. (2009). Acta Cryst. E65, o243.]); Ge & Li (2009[Ge, J.-Z. & Li, H. (2009). Acta Cryst. E65, o1179.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16N2O6

  • Mr = 404.37

  • Orthorhombic, P 21 21 21

  • a = 7.095 (16) Å

  • b = 15.14 (4) Å

  • c = 17.86 (5) Å

  • V = 1918 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.36 × 0.16 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 3043 measured reflections

  • 1881 independent reflections

  • 1440 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 1.01

  • 1881 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.10 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...O2i 0.93 2.59 3.361 (10) 140
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2099 ).


Acknowledgements

The authors thank the Thailand Research Fund (MRG 580182), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Education, Ministry of Education, Kasetsart University Research and Development Institute (5410127000) and the Department of Chemistry, Faculty of Science, Kasetsart University for financial support.

References

Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ge, J.-Z. & Li, H. (2009). Acta Cryst. E65, o1179.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Thorup, N., Deussen, H.-J., Bechgaard, K. & Bjørnholm, T. (2006). Acta Cryst. E62, o1342-o1343.  [CSD] [CrossRef] [ChemPort] [details]
Thoss, M., Seidel, R. W. & Feigel, M. (2009). Acta Cryst. E65, o243.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o682  [ doi:10.1107/S1600536813008660 ]

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