Bis(2,4-dinitro­phen­yl)sulfane

Buvaneswari, M.; Kalaivani, D.; Nethaji, M.

doi:10.1107/S1600536812041803

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 (C-C) = 0.004 Å
R = 0.046
wR = 0.110
Data-to-parameter ratio = 13.0
Details

Bis(2,4-dinitrophenyl)sulfane

M Buvaneswari,^a D Kalaivani ^a ^* and M Nethaji ^b

^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-HO 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); Alekhina et al. (1978); Parihar et al. (1971); Evans & Kinnard (1983); Andricopulo et al. (2006). For related syntheses, see: Pesin et al. (1963); Joshi & Mathur (1963); Obata et al. (1966); Stepanov et al. (1974); Davydov & Beletskaya (2003). For our previous work to synthesize new substituted barbiturates, see: Manickkam & Kalaivani (2011); Rajamani & Kalaivani (2012).

Experimental

Crystal data

C₁₂H₆N₄O₈S
M_r = 366.27
Monoclinic, P 2₁ /c
a = 9.9428 (12) Å
b = 7.3693 (9) Å
c = 19.743 (2) Å
= 95.525 (8)°
V = 1439.9 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.958, T_max = 0.991
15342 measured reflections
2949 independent reflections
1651 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.110
S = 0.99
2949 reflections
226 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O8ⁱ	0.93	2.54	3.080 (3)	117
C6-H6O7ⁱⁱ	0.93	2.49	3.364 (3)	156
C11-H11O2ⁱⁱⁱ	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); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
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.
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.
Evans, T. L. & Kinnard, R. D. (1983). J. Org. Chem. 48, 2496-2499.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Joshi, S. S. & Mathur, T. C. (1963). J. Indian Chem. Soc. 40, 939-940.
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.
Manickkam, V. & Kalaivani, D. (2011). Acta Cryst. E67, o3475.
Nakadate, M., Matsuyama, C. & Kimura, M. (1964). Chem. Pharm. Bull. 12, 1138-1143.
Obata, Y., Ishikawa, Y. & Nishino, C. (1966). Agric. Biol. Chem. 30, 164-168.
Parihar, D. B., Prakash, O., Bajaj, I., Tripathi, R. P. & Verma, K. K. (1971). J. Chromatogr. 59, 457-460.
Pesin, V. G., Khaletskii, A. M. & Vitenberg, I. G. (1963). Zh. Obshch. Khim. 33, 388-391.
Rajamani, K. & Kalaivani, D. (2012). Acta Cryst. E68, o2395.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stepanov, B. I., Rodionov, V. Ya. & Chivisova, T. A. (1974). Zh. Org. Khim. 10, 79-83.

organic compounds