7-Bromo-4b-methyl-7,8-dihydro-4bH-9-thia-8a-aza­fluorene 9,9-dioxide

Gallucci, J.C.; Dura, R.D.; Paquette, L.A.

doi:10.1107/S1600536808017972

Volume 64
Part 7
Page o1303
July 2008

Received 13 March 2008
Accepted 12 June 2008
Online 19 June 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.044
wR = 0.115
Data-to-parameter ratio = 9.7
Details

7-Bromo-4b-methyl-7,8-dihydro-4bH-9-thia-8a-azafluorene 9,9-dioxide

Judith C. Gallucci,^a ^* Robert D. Dura ^a and Leo A. Paquette ^a

^aEvans Chemical Laboratories, Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA
Correspondence e-mail: gallucci.1@osu.edu

The title compound, C₁₂H₁₂BrNO₂S, was isolated after direct irradiation (h [nu] 350 nm, hexane) of a mixture of stereoisomeric sulfonamides containing a vicinal dibromide and a conjugated diene. This product is one of a group of substrates that has contributed to our understanding of the photoreactivity patterns of non-bridged sulfonamides. The crystal structure was determined from a non-merohedrally twinned data set, where the twin law corresponded to a 180° rotation about the a* axis. The minor twin component refined to a value of 0.176 (3). The conformation of the molecule is planar at one end, as the benzene ring and the adjacent fused five-membered ring are coplanar, and U-shaped at the other end, where the five-membered ring is fused to the heterocyclic six-membered ring containing an allyl bromide group.

Related literature

For related chemistry, see: Dura & Paquette (2006); Paquette et al. (2004, 2006). For related literature, see: Cooper et al. (2002).

Experimental

Crystal data

C₁₂H₁₂BrNO₂S
M_r = 314.2
Monoclinic, P 2₁ /c
a = 14.3970 (3) Å
b = 7.8912 (1) Å
c = 11.4652 (2) Å
= 103.009 (1)°
V = 1269.13 (4) Å³
Z = 4
Mo K radiation
= 3.39 mm^-1
T = 293 (2) K
0.38 × 0.27 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) T_min = 0.650, T_max = 0.873
18122 measured reflections
2835 independent reflections
2401 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.115
S = 1.49
1509 reflections
156 parameters
H-atom parameters constrained
_max = 0.62 e Å^-3
_min = -0.29 e Å^-3

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RT2018 ).

References

Cooper, R. I., Gould, R. O., Parsons, S. & Watkin, D. J. (2002). J. Appl. Cryst. 35, 168-174.
Dura, R. D. & Paquette, L. A. (2006). J. Org. Chem. 71, 2456-2459.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Paquette, L. A., Barton, W. R. S. & Gallucci, J. C. (2004). Org. Lett. 6, 1313-1315.
Paquette, L. A., Dura, R. D., Fosnaugh, N. & Stepanian, M. (2006). J. Org. Chem. 71, 8438-8445.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds