7-Bromo-1-(4-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan

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

doi:10.1107/S160053681005436X

Volume 67
Part 2
Page o280
February 2011

Received 9 December 2010
Accepted 26 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.078
Data-to-parameter ratio = 16.8
Details

7-Bromo-1-(4-fluorophenylsulfonyl)-2-methylnaphtho[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

In the title compound, C₁₉H₁₂BrFO₃S, the 4-fluorophenyl ring makes a dihedral angle of 80.32 (5)° with the mean plane of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C-HO and C-H [pi] interactions. The crystal structure also exhibits aromatic [pi] - [pi] interactions between the central benzene rings of neighbouring molecules [centroid-centroid distance = 3.564 (3) Å].

Related literature

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984); Hranjec et al. (2003); Mahadevan & Vaidya (2003). For our previous structural studies of related 1-arylsulfonyl-7-bromo-2-methylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2008a,b).

Experimental

Crystal data

C₁₉H₁₂BrFO₃S
M_r = 419.26
Monoclinic, P 2₁ /n
a = 12.0415 (2) Å
b = 8.1579 (1) Å
c = 17.4578 (3) Å
= 105.325 (1)°
V = 1653.96 (5) Å³
Z = 4
Mo K radiation
= 2.64 mm^-1
T = 173 K
0.25 × 0.21 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.553, T_max = 0.744
14803 measured reflections
3803 independent reflections
3026 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.078
S = 1.02
3803 reflections
227 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14-C19 4-fluorophenyl ring.

D-HA	D-H	HA	DA	D-HA
C5-H5O2ⁱ	0.95	2.57	3.312 (3)	135
C18-H18O2ⁱⁱ	0.95	2.36	3.266 (3)	160
C19-H19O3ⁱ	0.95	2.57	3.113 (2)	117
C10-H10Cg1ⁱⁱⁱ	0.95	2.69	3.609 (2)	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: RK2255 ).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o944.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1158.
Einhorn, J., Demerseman, P., Royer, R., Cavier, R. & Gayral, P. (1984). Eur. J. Med. Chem. 19, 405-410.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hranjec, M., Grdisa, M., Pavelic, K., Boykin, D. W. & Karminski-Zamola, G. (2003). Farmaco, 58, 1319-1324.
Mahadevan, K. M. & Vaidya, V. P. (2003). Indian J. Pharm. Sci. 65, 128-34.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds