Bis(4-eth­oxy­phen­yl) sulfoxide

Meng, K.; Wu, C.; Cao, J.; Ma, P.; Liu, L.

doi:10.1107/S1600536811013213

Volume 67
Part 5
Page o1136
May 2011

Received 25 March 2011
Accepted 8 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.034
wR = 0.095
Data-to-parameter ratio = 18.1
Details

Bis(4-ethoxyphenyl) sulfoxide

Kang Meng,^a Cheng Wu,^a Jing Cao,^a Ping Ma ^a and Lihong Liu ^a ^*

^aPharmacy Department of the Second Artillery General Hospital, Beijing 100088, People's Republic of China
Correspondence e-mail: lihongliu2011@yahoo.cn

In the title compound, C₁₆H₁₈O₃S, the dihedral angle between the benzene rings is 82.7 (2)°. The O atom of the sulfoxide group is disordered over two orientations with refined occupancy factors of 0.563 (3):0.437 (3). In the crystal, molecules are linked by intermolecular C-HO hydrogen bonds, forming chains along the b axis.

Related literature

For background to Friedel-Crafts acylation, see: Edward & Sibelle (1963); DeHaan et al. (1979); Fillion & Fishlock (2005); Nishimoto et al. (2008). For the structures of related arylsulfoxides, see: Casarini et al. (2004); Noland & Kedrowski (2000).

Experimental

Crystal data

C₁₆H₁₈O₃S
M_r = 290.36
Triclinic, $[P \overline 1]$
a = 8.2052 (16) Å
b = 9.856 (2) Å
c = 10.196 (2) Å
= 64.71 (3)°
= 83.78 (3)°
= 82.88 (3)°
V = 738.4 (3) Å³
Z = 2
Mo K radiation
= 0.22 mm^-1
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007) T_min = 0.957, T_max = 0.974
6624 measured reflections
3450 independent reflections
2590 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.095
S = 1.06
3450 reflections
191 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	0.93	2.51	3.3013 (18)	143
Symmetry code: (i) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2577 ).

References

Casarini, D., Lunazzi, L., Mazzanti, A., Mercandelli, P. & Sironi, A. (2004). J. Org. Chem. 69, 3574-3577.
DeHaan, F. P., Covey, W. D., Delker, G. L., Baker, N. J., Feigon, J. F., Miller, K. D. & Stelter, E. D. (1979). J. Am. Chem. Soc. 101, 1336-1337.
Edward, J. W. R. & Sibelle, E. C. (1963). J. Org. Chem. 28, 674-676.
Fillion, E. & Fishlock, D. (2005). J. Am. Chem. Soc. 127, 13144-13145.
Nishimoto, Y., Babu, S. A., Yasuda, M. & Baba, A. (2008). J. Org. Chem. 73, 9465-9468.
Noland, W. E. & Kedrowski, B. L. (2000). Org. Lett. 2, 2109-2111.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds