7-Bromo-1-(4-chloro­phenyl­sulfan­yl)-2-phenyl­naphtho[2,1-b]furan

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

doi:10.1107/S1600536809052945

Volume 66
Part 1
Page o173
January 2010

Received 30 November 2009
Accepted 9 December 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.026
wR = 0.068
Data-to-parameter ratio = 17.2
Details

7-Bromo-1-(4-chlorophenylsulfanyl)-2-phenylnaphtho[2,1-b]furan

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

^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: uklee@pknu.ac.kr

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 [pi] - [pi] 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 [pi] interactions [3.505 (2) Å] between the Cl atom and the 2-phenyl ring are present.

Related literature

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).

Experimental

Crystal data

C₂₄H₁₄BrClOS
M_r = 465.77
Triclinic, $[P \overline 1]$
a = 8.2479 (3) Å
b = 8.3136 (4) Å
c = 13.9805 (6) Å
= 93.530 (2)°
= 99.317 (2)°
= 90.342 (2)°
V = 944.07 (7) Å³
Z = 2
Mo K radiation
= 2.44 mm^-1
T = 173 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.560, T_max = 0.887
16830 measured reflections
4364 independent reflections
3912 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.068
S = 1.05
4364 reflections
253 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.33 e Å^-3

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 ).

References

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.

organic compounds