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Volume 68 
Part 11 
Page o3116  
November 2012  

Received 22 September 2012
Accepted 5 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.110
Data-to-parameter ratio = 13.0
Details
Open access

Bis(2,4-dinitrophenyl)sulfane

aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India, and bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India
Correspondence e-mail: kalaivbalaj@yahoo.co.in

In the title compound, C12H6N4O8S, the dinitrophenyl rings subtend an angle of 78.46 (13) °. In the crystal, molecules are linked by weak C-H...O hydrogen bonds leading to the formation of a two-dimensional network lying parallel to the bc plane.

Related literature

For applications of bis(2,4-dinitrophenyl)sulfane, see: Nakadate et al. (1964[Nakadate, M., Matsuyama, C. & Kimura, M. (1964). Chem. Pharm. Bull. 12, 1138-1143.]); Alekhina et al. (1978[Alekhina, N. N., Gitis, S. S., Ivanov, A. V. & Kaminskii, A. Y. (1978). Zh. Org. Khim. 14, 2584-2587.]); Parihar et al. (1971[Parihar, D. B., Prakash, O., Bajaj, I., Tripathi, R. P. & Verma, K. K. (1971). J. Chromatogr. 59, 457-460.]); Evans & Kinnard (1983[Evans, T. L. & Kinnard, R. D. (1983). J. Org. Chem. 48, 2496-2499.]); Andricopulo et al. (2006[Andricopulo, A. D., Akoacheve, M. B., Krogh, R., Nickel, C., McLeish, M. J., Kenyon, G. L., Arscott, L. D., Williams, C. H., Daviond-Charvet, E. & Becker, K. (2006). Bioorg. Med. Chem. Lett. 16, 2283-2292.]). For related syntheses, see: Pesin et al. (1963[Pesin, V. G., Khaletskii, A. M. & Vitenberg, I. G. (1963). Zh. Obshch. Khim. 33, 388-391.]); Joshi & Mathur (1963[Joshi, S. S. & Mathur, T. C. (1963). J. Indian Chem. Soc. 40, 939-940.]); Obata et al. (1966[Obata, Y., Ishikawa, Y. & Nishino, C. (1966). Agric. Biol. Chem. 30, 164-168.]); Stepanov et al. (1974[Stepanov, B. I., Rodionov, V. Ya. & Chivisova, T. A. (1974). Zh. Org. Khim. 10, 79-83.]); Davydov & Beletskaya (2003[Davydov, D. V. & Beletskaya, I. P. (2003). Russ. J. Chem B. 52, 278-279.]). For our previous work to synthesize new substituted barbiturates, see: Manickkam & Kalaivani (2011[Manickkam, V. & Kalaivani, D. (2011). Acta Cryst. E67, o3475.]); Rajamani & Kalaivani (2012[Rajamani, K. & Kalaivani, D. (2012). Acta Cryst. E68, o2395.]).

[Scheme 1]

Experimental

Crystal data
  • C12H6N4O8S

  • Mr = 366.27

  • Monoclinic, P 21 /c

  • a = 9.9428 (12) Å

  • b = 7.3693 (9) Å

  • c = 19.743 (2) Å

  • [beta] = 95.525 (8)°

  • V = 1439.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 296 K

  • 0.15 × 0.06 × 0.03 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.991

  • 15342 measured reflections

  • 2949 independent reflections

  • 1651 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.110

  • S = 0.99

  • 2949 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O8i 0.93 2.54 3.080 (3) 117
C6-H6...O7ii 0.93 2.49 3.364 (3) 156
C11-H11...O2iii 0.93 2.57 3.489 (3) 168
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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 (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: WinGX (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: SU2502 ).


References

Alekhina, N. N., Gitis, S. S., Ivanov, A. V. & Kaminskii, A. Y. (1978). Zh. Org. Khim. 14, 2584-2587.  [ChemPort]
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Andricopulo, A. D., Akoacheve, M. B., Krogh, R., Nickel, C., McLeish, M. J., Kenyon, G. L., Arscott, L. D., Williams, C. H., Daviond-Charvet, E. & Becker, K. (2006). Bioorg. Med. Chem. Lett. 16, 2283-2292.  [CrossRef] [PubMed] [ChemPort]
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Davydov, D. V. & Beletskaya, I. P. (2003). Russ. J. Chem B. 52, 278-279.  [CrossRef] [ChemPort]
Evans, T. L. & Kinnard, R. D. (1983). J. Org. Chem. 48, 2496-2499.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Joshi, S. S. & Mathur, T. C. (1963). J. Indian Chem. Soc. 40, 939-940.  [ChemPort]
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]
Manickkam, V. & Kalaivani, D. (2011). Acta Cryst. E67, o3475.  [CSD] [CrossRef] [details]
Nakadate, M., Matsuyama, C. & Kimura, M. (1964). Chem. Pharm. Bull. 12, 1138-1143.  [CrossRef] [PubMed] [ChemPort]
Obata, Y., Ishikawa, Y. & Nishino, C. (1966). Agric. Biol. Chem. 30, 164-168.  [CrossRef] [ChemPort]
Parihar, D. B., Prakash, O., Bajaj, I., Tripathi, R. P. & Verma, K. K. (1971). J. Chromatogr. 59, 457-460.  [ChemPort]
Pesin, V. G., Khaletskii, A. M. & Vitenberg, I. G. (1963). Zh. Obshch. Khim. 33, 388-391.  [ChemPort]
Rajamani, K. & Kalaivani, D. (2012). Acta Cryst. E68, o2395.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stepanov, B. I., Rodionov, V. Ya. & Chivisova, T. A. (1974). Zh. Org. Khim. 10, 79-83.  [ChemPort]


Acta Cryst (2012). E68, o3116  [ doi:10.1107/S1600536812041803 ]

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