(3aR,6S,7aR)-7a-Bromo-2-[(4-methyl­phen­yl)sulfon­yl]-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­oxy­isoindole

Koşar, B.; Demircan, A.; Arslan, H.; Büyükgüngör, O.

doi:10.1107/S1600536811010750

Volume 67
Part 4
Pages o994-o995
April 2011

Received 5 March 2011
Accepted 22 March 2011
Online 31 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.048
wR = 0.126
Data-to-parameter ratio = 16.6
Details

(3aR,6S,7aR)-7a-Bromo-2-[(4-methylphenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

Basak Kosar,^a ^* Aydin Demircan,^b Hakan Arslan ^c and Orhan Büyükgüngör ^d

^aDepartment of Science Education, Faculty of Education, Sinop University, 57100-Sinop, Turkey,^bDepartment of Chemistry, Faculty of Arts and Sciences, Nigde University, 51240-Nigde, Turkey,^cDepartment of Chemistry, Faculty of Arts and Science, Mersin University, 33343-Mersin, Turkey, and ^dDepartment of Physics, Arts and Sciences Faculty, Ondokuz Mayis University, 55139-Samsun, Turkey
Correspondence e-mail: bkosar@sinop.edu.tr

In the title compound, C₁₅H₁₆BrNO₃S, the boat form of the six-membered ring is almost symmetrical with respect to the epoxy bridge. The two five-membered rings generated by the epoxy bridge of the six-membered ring adopt envelope conformations, whereas the N-containing five-membered ring adopts a twisted conformation. In the crystal, molecules are linked by C-HO hydrogen bonds.

Related literature

For general background to intramolecular Diels-Alder reactions and heteroaromatic Diels-Alder reactions, see: Dell (1998); Kappe et al. (1997); Arai et al. (2010); Lohse & Hsung (2009). For related structures, see: Kosar et al. (2006, 2007a,b). For the synthesis of the title compound and related compounds, see: Carlini et al. (1997); Hart et al. (1997); Shing et al. (1996); Karaarslan et al. (2007); Pontén & Magnusson (1997); Demircan et al. (2006); Arslan & Demircan (2008); Demircan & Parsons (1998). For puckering analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₅H₁₆BrNO₃S
M_r = 370.26
Monoclinic, P 2₁ /c
a = 16.5136 (6) Å
b = 6.2186 (3) Å
c = 16.3487 (7) Å
= 113.802 (3)°
V = 1536.07 (12) Å³
Z = 4
Mo K radiation
= 2.82 mm^-1
T = 296 K
0.58 × 0.44 × 0.31 mm

Data collection

STOE IPDS 2 CCD diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.310, T_max = 0.495
7305 measured reflections
3163 independent reflections
2353 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.126
S = 1.07
3163 reflections
190 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6AO1ⁱ	0.97	2.50	3.382 (6)	151
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2, publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2354 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the diffractometer (purchased under grant F.279 of University Research Fund) and also the Scientific & Technological Research Council of Turkey (TÜBITAK) for financial support of this work (PN: 107 T831).

References

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organic compounds