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Volume 69 
Part 5 
Pages o808-o809  
May 2013  

Received 7 April 2013
Accepted 23 April 2013
Online 30 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.141
Data-to-parameter ratio = 24.3
Details
Open access

1,2-Bis(2,4-dinitrophenyl)disulfane

aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
Correspondence e-mail: kalaivbalaj@yahoo.co.in

In the title molecule, C12H6N4O8S2, the dihedral angle between the benzene rings is 77.00 (8)°. The mean planes of the nitro groups are twisted slightly from the benzene rings, forming dihedral angles in the range 2.3 (2)-8.6 (3)°. The S-S bond length is 2.0458 (7) Å. Each S atom is essentially coplanar with the benzene ring to which it is attached, with deviations from the ring planes of 0.0163 (5) and 0.0538 (5) Å. In the crystal, molecules are linked through weak C-H...O hydrogen bonds, forming a two-dimensional network parallel to (001).

Related literature

For synthetic applications of disulfides, see: Khavasch et al. (1950[Khavasch, N., Gleason, G. J. & Buess, C. M. (1950). J. Am. Chem. Soc. 72, 1796-1798.]); Mitin & Zaperalova (1974[Mitin, Yu. V. & Zaperalova, N. P. (1974). Zh. Obshch. Khim. 44, 2074-2075.]); Stepanov et al. (1974[Stepanov, B. I., Rodionov, V. Ya. & Chibisova, T. A. (1974). Zh. Org. Khim. 10, 79-83.], 1977[Stepanov, B. I., Rodionov, V. Ya., Chibisova, T. A., Yogodina, L. A. & Stankevich, A. D. (1977). Zh. Org. Khim. 13, 370-374.]); Cochran et al. (1996[Cochran, J. C., Friedman, S. R. & Frazier, J. P. (1996). J. Org. Chem. 61, 1533-1536.]). For the natural occurrence of disulfides, see: Ramadas & Srinivasan (1995[Ramadas, K. & Srinivasan, N. (1995). Synth. Commun. 25, 227-234.]). For the preparation procedures for disulfides, see: Khavasch & Cameron (1951[Khavasch, N. & Cameron, J. L. (1951). J. Am. Chem. Soc. 73, 3864-3867.]); Traynelis & Rieck (1973[Traynelis, V. J. & Rieck, J. N. (1973). J. Org. Chem. 38, 4339-4341.]); Bilozor & Boldyrev (1984[Bilozor, T. K. & Boldyrev, B. G. (1984). Zh. Org. Khim. 20, 889-890.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Glidewell et al. (2000[Glidewell, C., Low, J. N. & Wardell, J. L. (2000). Acta Cryst. B56, 893-905.]); Song & Fan (2009[Song, M. & Fan, C. (2009). Acta Cryst. E65, o2835.]); Xiao et al. (2010[Xiao, Q., Liu, R., Li, Y.-H., Chen, H.-B. & Zhu, H.-J. (2010). Acta Cryst. E66, o606.]); Buvaneswari et al. (2012[Buvaneswari, M., Kalaivani, D. & Nethaji, M. (2012). Acta Cryst. E68, o3116.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H6N4O8S2

  • Mr = 398.33

  • Monoclinic, P 21 /c

  • a = 11.3776 (6) Å

  • b = 11.9579 (5) Å

  • c = 11.0459 (6) Å

  • [beta] = 90.943 (2)°

  • V = 1502.62 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.804, Tmax = 0.922

  • 22589 measured reflections

  • 5706 independent reflections

  • 3983 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.141

  • S = 1.02

  • 5706 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.54 3.341 (3) 144
C8-H8...O3ii 0.93 2.60 3.403 (2) 144
C12-H12...O6iii 0.93 2.42 3.139 (2) 134
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y-1, z; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5606 ).


Acknowledgements

The authors thank the IIT Madras for the data collection and the University Grants Commission, New Delhi, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bilozor, T. K. & Boldyrev, B. G. (1984). Zh. Org. Khim. 20, 889-890.  [ChemPort]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Buvaneswari, M., Kalaivani, D. & Nethaji, M. (2012). Acta Cryst. E68, o3116.  [CrossRef] [details]
Cochran, J. C., Friedman, S. R. & Frazier, J. P. (1996). J. Org. Chem. 61, 1533-1536.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Glidewell, C., Low, J. N. & Wardell, J. L. (2000). Acta Cryst. B56, 893-905.  [CSD] [CrossRef] [details]
Khavasch, N. & Cameron, J. L. (1951). J. Am. Chem. Soc. 73, 3864-3867.
Khavasch, N., Gleason, G. J. & Buess, C. M. (1950). J. Am. Chem. Soc. 72, 1796-1798.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Mitin, Yu. V. & Zaperalova, N. P. (1974). Zh. Obshch. Khim. 44, 2074-2075.  [ChemPort]
Ramadas, K. & Srinivasan, N. (1995). Synth. Commun. 25, 227-234.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Song, M. & Fan, C. (2009). Acta Cryst. E65, o2835.  [CrossRef] [details]
Stepanov, B. I., Rodionov, V. Ya. & Chibisova, T. A. (1974). Zh. Org. Khim. 10, 79-83.  [ChemPort]
Stepanov, B. I., Rodionov, V. Ya., Chibisova, T. A., Yogodina, L. A. & Stankevich, A. D. (1977). Zh. Org. Khim. 13, 370-374.  [ChemPort]
Traynelis, V. J. & Rieck, J. N. (1973). J. Org. Chem. 38, 4339-4341.  [CrossRef] [ChemPort]
Xiao, Q., Liu, R., Li, Y.-H., Chen, H.-B. & Zhu, H.-J. (2010). Acta Cryst. E66, o606.  [CrossRef] [details]


Acta Cryst (2013). E69, o808-o809   [ doi:10.1107/S1600536813011082 ]

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