7-Bromo-2-methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan

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

doi:10.1107/S160053680801177X

Volume 64
Part 5
Page o944
May 2008

Received 15 April 2008
Accepted 24 April 2008
Online 30 April 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.024
wR = 0.079
Data-to-parameter ratio = 14.1
Details

7-Bromo-2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan

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

The title compound, C₁₉H₁₃BrO₃S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic [pi] - [pi] stacking interactions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring molecules; the centroid-centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked molecules exhibit C-H [pi] , inter- and intramolecular C-HO interactions.

Related literature

For the crystal structures of similar 7-bromonaphtho[2,1-b]furan compounds, see: Choi et al. (2006, 2007).

Experimental

Crystal data

C₁₉H₁₃BrO₃S
M_r = 401.26
Triclinic, $[P \overline 1]$
a = 7.8583 (7) Å
b = 8.0025 (7) Å
c = 13.278 (1) Å
= 107.429 (1)°
= 93.678 (1)°
= 90.417 (2)°
V = 794.72 (12) Å³
Z = 2
Mo K radiation
= 2.73 mm^-1
T = 173 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.381, T_max = 0.571
6371 measured reflections
3084 independent reflections
2874 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.023
wR(F²) = 0.078
S = 1.17
3084 reflections
218 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7Cg1ⁱ	0.95	2.85	3.764 (3)	161
C4-H4O2	0.95	2.44	3.226 (3)	140
C16-H16O3ⁱⁱ	0.95	2.56	3.257 (3)	130
C19-H19AO3	0.98	2.28	2.926 (3)	122
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z. Cg1 is the centroid of the C13-C18 ring.

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: JH2063 ).

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. (2006). Acta Cryst. E62, o5876-o5877.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o4102.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds