Received 30 November 2009
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea,bDepartment of Molecular Biology, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and cDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
Correspondence e-mail: email@example.com
In the title compound, C24H14BrClOS, the S-bound 4-chlorophenyl ring is nearly perpendicular to the plane of the naphthofuran fragment [dihedral angle = 83.34 (3)°] and the phenyl ring in the 2-position is rotated out of the naphthofuran plane by a dihedral angle of 15.23 (5)°. The crystal structure is stabilized by aromatic - interactions between the furan and the central benzene rings of the neighbouring naphthofuran fragments, and between the outer benzene rings of the neighbouring naphthofuran fragments; the centroid-centroid distances within the stack are 3.879 (2) and 3.857 (2) Å. In addition, intermolecular C-Cl interactions [3.505 (2) Å] between the Cl atom and the 2-phenyl ring are present.
For the crystal structures of similar 7-bromo-2-phenylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2009a,b). For the biological activity of naphthofuran compounds, see: Hagiwara et al. (1999); Hranjec et al. (2003); Mahadevan & Vaidya (2003).
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: BG2314 ).
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). SADABS. APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o1812.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1956.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hagiwara, H., Sato, K., Suzuki, T. & Ando, M. (1999). Heterocycles, 51, 497-500.
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, 128-134.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.