Tetra-O-4-methyl­phenyl­sulfonyl­penta­erythritol

Li, S.-X.; Zhu, L.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S1600536808020643

Volume 64
Part 8
Pages o1474-o1475
August 2008

Received 30 June 2008
Accepted 4 July 2008
Online 12 July 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.120
Data-to-parameter ratio = 22.6
Details

Tetra-O-4-methylphenylsulfonylpentaerythritol

Shu-Xian Li,^a,^b Lin Zhu,^b Hoong-Kun Fun ^c ^* and Suchada Chantrapromma ^d ⁺

^aDepartment of Chemistry, Handan College, Handan, Hebei 056005, People's Republic of China,^bDepartment of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China,^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title molecule (systematic name: methanetetrayltetramethylene tetra-p-toluenesulfonate), C₃₃H₃₆O₁₂S₄, the central C atom and the S atoms exhibit distorted tetrahedral configurations. The aromatic rings in opposite arms are nearly parallel to each other, with a dihedral angle of 10.26 (8) or 3.45 (9)°. The molecules are linked into a two-dimensional network parallel to the bc plane by weak C-HO hydrogen bonds, [pi] - [pi] [centroid-centroid distance = 3.5806 (12) Å] and S-O [pi] [Ocentroid = 3.1455 (15) Å and S-Ocentroid = 122.41 (7)°] intermolecular interactions. Intramolecular C-HO hydrogen bonds are also present.

Related literature

For bond-length data, see: Allen et al. (1987). For a related structure, see: Li et al. (2008). For general background and applications of pentaerythritol derivatives, see: Constable et al. (1998); Fundueanu et al. (1998); Jiang et al. (2002); Kim et al. (2000); Luo & Chen (2001); Mischiati et al. (2001); Oike et al. (2001).

Experimental

Crystal data

C₃₃H₃₆O₁₂S₄
M_r = 752.86
Monoclinic, P 2₁ /c
a = 13.2983 (2) Å
b = 18.0368 (2) Å
c = 15.4181 (2) Å
= 110.653 (1)°
V = 3460.50 (8) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 100.0 (1) K
0.47 × 0.41 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.857, T_max = 0.949
45048 measured reflections
10090 independent reflections
7927 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.119
S = 1.04
10090 reflections
446 parameters
H-atom parameters constrained
_max = 0.66 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2CO4	0.97	2.48	2.849 (2)	102
C3-H3BO6	0.97	2.47	2.905 (2)	107
C3-H3BO7	0.97	2.55	2.876 (2)	100
C3-H3CO9ⁱ	0.97	2.46	3.433 (2)	175
C4-H4AO4	0.97	2.55	2.879 (2)	100
C5-H5BO12	0.97	2.44	2.888 (2)	107
C5-H5CO7	0.97	2.49	2.8396 (19)	101
C7-H7AO2	0.93	2.58	2.937 (2)	103
C8-H8BO11ⁱⁱ	0.93	2.52	3.140 (2)	124
C10-H10AO6ⁱ	0.93	2.41	3.257 (2)	151
C18-H18AO6	0.93	2.59	2.932 (2)	103
C22-H22AO12ⁱⁱⁱ	0.93	2.52	3.154 (2)	126
C25-H25AO8	0.93	2.56	2.924 (2)	104
C28-H28AO12	0.93	2.54	2.905 (2)	104
C29-H29AO8^iv	0.93	2.42	3.334 (2)	165
C31-H31AO12ⁱⁱⁱ	0.93	2.53	3.209 (2)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2625 ).

Acknowledgements

The authors gratefully acknowledge the financial assistance of Beijing Normal University. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Constable, E. C., Housecroft, C. E., Cattalini, M. & Phillips, D. (1998). New J. Chem. pp. 193-200.
Fundueanu, G., Esposito, E., Mihai, D., Carpov, A., Desbrieres, J., Rinaudo, M. & Nastruzzi, C. (1998). Int. J. Pharm. 170, 11-21.
Jiang, H., Lee, S. J. & Lin, W. (2002). Org. Lett. 4, 2149-2152.
Kim, J., Leong, A. J., Lindoy, L. F., Kim, J., Nachbaur, J., Nezhadali, A., Rounaghi, G. & Wei, G. (2000). J. Chem. Soc. Dalton Trans. pp. 3453-3459.
Li, S.-X., Li, H.-M., Lu, Z.-L., Fun, H.-K. & Chantrapromma, S. (2008). Acta Cryst. E64, o1472-o1473.
Luo, F. T. & Chen, C. H. (2001). Heterocycles, 55, 1663-1678.
Mischiati, C., Jeang, K.-T., Feriotto, G., Breda, L., Borgatti, M., Bianchi, N. & Gambari, R. (2001). Antisense Nucleic Acid Drug Dev. 11, 209-217.
Oike, H., Hamada, M., Eguchi, S., Danda, Y. & Tezuka, Y. (2001). Macromolecules, 34, 2776-2782.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds