3,3′-Dibutanoyl-1,1′-(o-phenyl­ene)dithio­urea

Saeed, A.; Abbas, N.; Rafique, H.; Bolte, M.

doi:10.1107/S1600536810001789

Volume 66
Part 2
Page o441
February 2010

Received 11 December 2009
Accepted 14 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.095
Data-to-parameter ratio = 14.7
Details

3,3'-Dibutanoyl-1,1'-(o-phenylene)dithiourea

Aamer Saeed,^a ^* Naeem Abbas,^a Hummera Rafique ^a and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: aamersaeed@yahoo.com

The molecular conformation of the title compound, C₁₆H₂₂N₄O₂S₂, is stabilized by two intramolecular N-HO hydrogen bonds. The crystal packing shows N-HO and N-HS hydrogen bonds.

Related literature

For details of the biological activity of bisthioureas, see: Berkessel et al. (2006); Moloto et al. (2004). For their applications, see: Atia et al. (2005); Hu et al. (2009); Phetsuksiri et al. (2003). For the synthesis of the title compound, see: Succaw et al. (2005).

Experimental

Crystal data

C₁₆H₂₂N₄O₂S₂
M_r = 366.50
Monoclinic, P 2₁ /n
a = 8.8099 (5) Å
b = 16.4925 (7) Å
c = 12.3923 (8) Å
= 91.949 (5)°
V = 1799.53 (17) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 173 K
0.28 × 0.28 × 0.23 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) T_min = 0.918, T_max = 0.932
22483 measured reflections
3360 independent reflections
2890 reflections with I > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.095
S = 1.04
3360 reflections
229 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11O1	0.86 (2)	1.90 (2)	2.6336 (17)	142.6 (17)
N12-H12O2ⁱ	0.84 (2)	2.19 (2)	3.0309 (18)	175.3 (19)
N21-H21O2	0.83 (2)	1.98 (2)	2.6616 (18)	139.1 (18)
N22-H22S1ⁱⁱ	0.87 (2)	2.75 (2)	3.6147 (14)	172.0 (17)
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2318 ).

Acknowledgements

NA gratefully acknowledges a research scholarship from the HEC Islamabad under the HEC Indigenous PhD Scholarship 5000 Scheme

References

Atia, A. A. (2005). Hydrometallurgy, 80, 98-106.
Berkessel, A., Roland, K. & Neudorfl, J. M. (2006). Org. Lett. 8, 4195-4198.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Hu, C., He, Y., Chen, Z. & Huang, X. (2009). Tetrahedron Asymmetry, 20, 98-106.
Moloto, M. L. & Revaprasadu, N. (2004). J. Mater. Sci. 15, 313-316.
Phetsuksiri, B., Jackson, M., Scherman, H., McNeil, M., Besra, G. S., Baulard, A. R., Slayden, R. A., DeBarber, A. E., Barry, C. E., Baird, M. S., Crick, D. C. & Brennan, P. J. (2003). J. Biol. Chem. 278, 53123-53130.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Succaw, G. L., Weakley, T. J. R., Han, H. & Doxsee, K. M. (2005). Cryst. Growth Des. 5, 2288-2298.

organic compounds