Bis(4,6-diamino­pyrimidin-2-yl) disulfide dimethyl sufoxide disolvate

Papastavrou, E.; Shakhatreh, S.; Akrivos, P.D.; Gdaniec, M.

doi:10.1107/S160053680802480X

Volume 64
Part 9
Page o1724
September 2008

Received 31 July 2008
Accepted 1 August 2008
Online 9 August 2008

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.030
wR = 0.078
Data-to-parameter ratio = 15.3
Details

Bis(4,6-diaminopyrimidin-2-yl) disulfide dimethyl sufoxide disolvate

Ephthymia Papastavrou,^a Saleh Shakhatreh,^b Pericles D. Akrivos ^a and Maria Gdaniec ^c ^*

^aDepartment of Chemistry, Aristotle University of Thessaloniki, 54006 Thessaloniki, Greece,^bAl Huson University College, Al Balqa' Applied University, Al-Huson, Jordan, and ^cFaculty of Chemistry, Adam Mickiewicz University, 60-780 Poznan, Poland
Correspondence e-mail: magdan@amu.edu.pl

The title compound, C₈H₁₀N₈S₂·2C₂H₆SO, was obtained unintentionally during an attempt to prepare a thiolate derivative of trimethyltin. The complete disulfide molecule is generated by twofold rotation symmetry and the C-S-S-C torsion angle around the S-S bond is -85.70 (10)°. The molecules are connected via N-HN hydrogen bonds into strongly corrugated layers parallel to (001), generating an R₂²(8) motif. The solvent molecule, which exhibits minor disorder of its S atom [site occupancies = 0.9591 (18) and 0.0409 (18)], is linked to this layer via a pair of N-HO interactions.

Related literature

For information on the preferred conformations of organic disulfides, see: Saczewski et al. (2006).

Experimental

Crystal data

C₈H₁₀N₈S₂·2C₂H₆OS
M_r = 438.62
Orthorhombic, P c c n
a = 11.2612 (4) Å
b = 11.9948 (5) Å
c = 15.0754 (6) Å
V = 2036.32 (14) Å³
Z = 4
Mo K radiation
= 0.49 mm^-1
T = 130 (2) K
0.40 × 0.10 × 0.10 mm

Data collection

Kuma KM-4-CCD geometry diffractometer
Absorption correction: none
17524 measured reflections
2240 independent reflections
1944 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.078
S = 1.04
2240 reflections
146 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7AO1ⁱ	0.78 (2)	2.20 (2)	2.959 (2)	165 (2)
N7-H7BN1ⁱⁱ	0.846 (19)	2.33 (2)	3.169 (2)	175.1 (16)
N8-H8AO1ⁱⁱⁱ	0.84 (2)	2.09 (2)	2.9109 (19)	164.4 (18)
N8-H8BN3^iv	0.81 (2)	2.33 (2)	3.088 (2)	156.8 (19)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2773 ).

References

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.
Saczewski, J., Frontera, A., Gdaniec, M., Brzozowski, Z., Saczewski, F., Tabin, P., Quinoñero, D. & Deyà, P. M. (2006). Chem. Phys. Lett. 422, 234-239.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1989). Stereochemical Workstation Operation Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds