5-Bromo-2,4,6-trimethyl-3-methyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808032467

Volume 64
Part 11
Page o2117
November 2008

Received 1 October 2008
Accepted 8 October 2008
Online 15 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
Disorder in main residue
R = 0.042
wR = 0.112
Data-to-parameter ratio = 13.8
Details

5-Bromo-2,4,6-trimethyl-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
Correspondence e-mail: uklee@pknu.ac.kr

In the title compound, C₁₂H₁₃BrO₂S, there are two symmetry-independent molecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The methylsulfinyl group in molecule B is disordered over two positions with site-occupancy factors fixed at 0.6 and 0.4. The crystal structure is stabilized by C-HO hydrogen bonds and intermolecular C-H [pi] interactions. In addition, the crystal structure exhibits C-Br [pi] interactions, with C-BrCg1 = 3.646 (8) Å where Cg1 is the centroid of the furan ring.

Related literature

For the crystal structures of similar 3-methylsulfinyl-1-benzofuran compounds, see: Choi et al. (2007a,b).

Experimental

Crystal data

C₁₂H₁₃BrO₂S
M_r = 301.19
Monoclinic, C c
a = 28.128 (4) Å
b = 11.013 (1) Å
c = 8.052 (1) Å
= 102.290 (2)°
V = 2437.1 (5) Å³
Z = 8
Mo K radiation
= 3.53 mm^-1
T = 298 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) T_min = 0.269, T_max = 0.345
7147 measured reflections
4360 independent reflections
3737 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.112
S = 1.09
4360 reflections
317 parameters
2 restraints
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.90 e Å^-3
Absolute structure: Flack (1983), 1736 Friedel pairs
Flack parameter: 0.70 (2)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
C12-H12AO2ⁱ	0.96	2.34	3.298 (9)	179
C12-H12CO4Bⁱⁱ	0.96	2.42	3.168 (12)	134
C24A-H24AO4Aⁱⁱⁱ	0.96	2.35	3.199 (13)	148
C9-H9ACg2ⁱⁱⁱ	0.96	3.30	3.943 (9)	124
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2545 ).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o521-o522.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o1823-o1824.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds