2,5-Bis(2-naphthylmethylsulfanyl)-1-thia- 3,4-diazacyclopenta-2,5-diene Fiona N.-F. How, a *‡ David J. Watkin, b Karen A. Crouse a and M. Ibrahim M. Tahir a a Department of Chemistry, Universiti Putra Malaysia, 43400 UPM, Selangor, Malaysia, and b Chemical Crystallography, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, England Correspondence e-mail: howfiona@gmail.com Received 11 May 2007; accepted 16 May 2007 Key indicators: single-crystal X-ray study; T = 150 K; mean (C–C) = 0.002 A ˚ ; R factor = 0.034; wR factor = 0.072; data-to-parameter ratio = 18.1. The title molecule, C 24 H 18 N 2 S 3 , consists of three essentially planar fragments viz. two methylnaphthalene groups and a five-membered thiadiazole ring. The dihedral angles between the two methylnaphthalene groups and the central 1-thia-3,4- diazacyclopenta-2,5-diene group are 78.9 (1) and 68.8 (1)  . In the crystal structure, - stacking interactions exist between pairs of symmetry-related naphthalene fragments with an interplanar separation of 3.35 A ˚ . All bond lengths and angles are comparable with previous reports except that both C—S bond lengths are slightly longer than normal. In addition, the C—S—C and S—C—C bond angles appear to be smaller than normal and this could be due to the steric hindrance of the methylnaphthalene fragments. Related literature Similar compounds have been discovered unintentionally by crystallization of dithiocarbazate compounds (Tarafder, Aza- hari et al., 2000; Tarafder, Saravanan et al., 2000). For related literature, see: Allen et al. (1987); Go ¨ rbitz (1999); Shanmuga Sundara Raj et al. (2000). Experimental Crystal data C 24 H 18 N 2 S 3 M r = 430.62 Monoclinic, P2 1 =a a = 8.2095 (1) A ˚ b = 12.9738 (2) A ˚ c = 18.8054 (3) A ˚  = 93.2975 (7)  V = 1999.62 (5) A ˚ 3 Z =4 Mo K radiation  = 0.39 mm 1 T = 150 K 0.62  0.60  0.45 mm Data collection Bruker-Nonius KappaCCD diffractometer Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) T min = 0.56, T max = 0.84 23179 measured reflections 4734 independent reflections 4734 reflections with I > 3(I) R int = 0.013 Refinement R[F 2 >2(F 2 )] = 0.034 wR(F 2 ) = 0.072 S = 0.98 4734 reflections 262 parameters H-atom parameters constrained Á max = 0.37 e A ˚ 3 Á min = 0.26 e A ˚ 3 Table 1 Selected geometric parameters (A ˚ ,  ). S6—C7 1.8360 (13) S18—C19 1.8339 (13) S6—C7—C8 106.47 (8) C1—S18—C19 99.93 (6) Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduc- tion: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al. , 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al. , 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS. FNHF gratefully acknowledges MOSTI, Malaysia for an attachment grant under an NSF scholarship and the Chemical Crystallography Laboratory, Oxford University for instru- mental facilities. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2391). 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, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Go ¨ rbitz, C. H. (1999). Acta Cryst. B55, 1090–1098. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Shanmuga Sundara Raj, S., Yamin, B. M., Yussof, Y. A., Tarafder, M. T. H., Fun, H.-K. & Grouse, K. A. (2000). Acta Cryst. C56, 1236–1237. Tarafder, M. T. H., Azahari, K., Crouse, K. A., Yamin, B. M., Sundara Raj, S. S., Ibrahim, A. R. & Fun, H.-K. (2000). Z. Kristallogr. New Cryst. Struct. 215, 487–488. Tarafder, M. T. H., Saravanan, N., Yamin, B. M., Sundara Raj, S. S., Ibrahim, A. R. & Fun, H.-K. (2000). Z. Kristallogr. New Cryst. Struct. 215, 485–486. Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. organic compounds Acta Cryst. (2007). E63, o2913 doi:10.1107/S1600536807024257 # 2007 International Union of Crystallography o2913 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 ‡ Current address: Chemical Crystallography, Chemistry Research Labora- tory, 12 Mansfield Road, Oxford OX1 3TA, England.