2,4,6-Tris(1-oxo-2-pyridylsulfanylmeth­yl)mesitylene methanol solvate

Ravindran Durai Nayagam, B.; Jebas, S.R.; Ravi Samuelraj, C.; Schollmeyer, D.

doi:10.1107/S1600536808013081

Volume 64
Part 6
Pages o1036-o1037
June 2008

Received 1 May 2008
Accepted 3 May 2008
Online 10 May 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.151
Data-to-parameter ratio = 15.1
Details

2,4,6-Tris(1-oxo-2-pyridylsulfanylmethyl)mesitylene methanol solvate

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b C. Ravi Samuelraj ^a and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamil Nadu, India,^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

In the title compound, C₂₇H₂₇N₃O₃S₃·CH₄O, the dihedral angles formed by the mesitylene ring with the three oxopyridyl rings are 89.6 (1), 75.5 (1) and 80.69 (1)°, indicating that all three are nearly perpendicular to the mesitylene ring. Intramolecular C-HS hydrogen bonds generate S(6) ring motifs. The crystal structure is stabilized by intramolecular C-HS and intermolecular C-HO hydrogen bonds and weak C-H [pi] interactions.

Related literature

For related literature on the biological activity of N-oxides see: Lobana et al., (1989); Symons & West (1985); Katsuyuki et al. (1991); Bovin et al. (1992); Leonard et al.(1955). For related literature on N-oxides, see: Jebas et al. (2005); Ravindran et al. (2008). For bond-length data, see: Allen et al. (1987); Jebas et al. (2005); Ravindran et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₇H₂₇N₃O₃S₃·CH₄O
M_r = 569.74
Monoclinic, P 2₁ /c
a = 11.9644 (17) Å
b = 14.9129 (8) Å
c = 15.467 (2) Å
= 91.733 (7)°
V = 2758.4 (6) Å³
Z = 4
Cu K radiation
= 2.78 mm^-1
T = 298 (2) K
0.52 × 0.42 × 0.06 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.296, T_max = 0.842
5226 measured reflections
5226 independent reflections
4156 reflections with I > 2(I)
3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.150
S = 1.08
5226 reflections
347 parameters
12 restraints
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1L-H1LO27	0.82	2.41	2.804 (7)	110
C16-H16AO36ⁱ	0.96	2.47	3.348 (4)	152
C16-H16BS20	0.96	2.68	3.420 (3)	135
C18-H18BS29	0.96	2.79	3.515 (3)	133
C25-H25O7ⁱⁱ	0.93	2.44	3.147 (5)	133
C28-H28AO7ⁱ	0.97	2.48	3.397 (3)	157
C31-H31O27ⁱⁱⁱ	0.93	2.35	3.107 (4)	139
C2-H2Cg1^iv	0.93	2.91	3.774 (3)	154
C4-H4Cg1^v	0.93	2.67	3.377 (3)	134
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) -x+1, -y+1, -z; (v) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1 is the centroid of the C10-C15 ring.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (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: AT2565 ).

Acknowledgements

BRDN thanks the University Grants Commission, India, for a Teacher Fellowship.

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-S19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chim. Fr. 129, 145-150.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Jebas, S. R., Balasubramanian, T., Ravidurai, B. & Kumaresan, S. (2005). Acta Cryst. E61, o2677-o2678.
Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099-5100.
Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261-264.
Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394-401.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Ravindran Durai Nayagam, B., Jebas, S. R., Grace, S. & Schollmeyer, D. (2008). Acta Cryst. E64, o409.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Symons, M. C. R. & West, D.-X. (1985). J. Chem. Soc. Dalton Trans. pp. 379-381.

organic compounds