(3aR,6S,7aR)-7a-Bromo-2-methyl-sulfonyl-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-isoindole.

In the title compound, C(9)H(12)BrNO(3)S, the two tetra-hydro-furan rings adopt envelope conformations, the pyrrolidine ring adopts a half-chair conformation and the six-membered ring is in a boat conformation. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into R(2) (2)(8) and R(2) (2)(14) rings along the b-axis direction.

Related literature

For a related structure, see: Koşar et al. (2006 ▶). For uses of sulfonamides in medicine, in particular the treatment of bacterial infection, see: Kleemann et al. (1999 ▶); Cremlyn (1996 ▶). For the synthesis of sulfonamides, see: Anderson (1979 ▶). For thermal intra­molecular Diels–Alder reaction of furans (IMDAF), see: Demircan & Parsons (2002 ▶); Arslan et al. (2008 ▶). A mesyl group in the structure is normally chosen as a protective group for nitro­gen, but at the same time accelerates the cyclo­addition process for IMDAF, see: Greene (1981 ▶); Choony et al. (1997 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H12BrNO3S

M = 294.17

Triclinic,

a = 5.9478 (7) Å

b = 9.5869 (10) Å

c = 10.7775 (11) Å

α = 114.307 (8)°

β = 90.481 (9)°

γ = 97.812 (9)°

V = 553.46 (10) Å3

Z = 2

Mo Kα radiation

μ = 3.89 mm−1

T = 296 K

0.38 × 0.23 × 0.08 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2001 ▶) T min = 0.223, T max = 0.682

8163 measured reflections

2293 independent reflections

1920 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.107

S = 1.10

2293 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.44 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015959/hg5029sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015959/hg5029Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015959/hg5029Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H12BrNO3S	Z = 2
Mr = 294.17	F(000) = 296
Triclinic, P1	Dx = 1.765 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9478 (7) Å	Cell parameters from 8163 reflections
b = 9.5869 (10) Å	θ = 2.1–27.5°
c = 10.7775 (11) Å	µ = 3.89 mm−1
α = 114.307 (8)°	T = 296 K
β = 90.481 (9)°	Block, light-brown
γ = 97.812 (9)°	0.38 × 0.23 × 0.08 mm
V = 553.46 (10) Å3

Stoe IPDS 2 diffractometer	2293 independent reflections
Radiation source: fine-focus sealed tube	1920 reflections with I > 2σ(I)
graphite	Rint = 0.082
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.1°
rotation method scans	h = −7→7
Absorption correction: integration (X-RED; Stoe & Cie, 2001)	k = −12→12
Tmin = 0.223, Tmax = 0.682	l = −13→13
8163 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.3277P] where P = (Fo2 + 2Fc2)/3
2293 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.7380 (6)	0.3068 (4)	0.6385 (4)	0.0348 (8)
C2	0.8248 (7)	0.1507 (5)	0.5964 (4)	0.0438 (9)
H2A	0.9770	0.1543	0.5651	0.053*
H2B	0.7234	0.0668	0.5264	0.053*
C3	0.8218 (9)	0.1363 (5)	0.7338 (5)	0.0553 (11)
H3	0.9189	0.0654	0.7421	0.066*
C4	0.5780 (9)	0.1066 (6)	0.7645 (5)	0.0577 (12)
H4	0.4995	0.0132	0.7588	0.069*
C5	0.4970 (8)	0.2380 (6)	0.8007 (4)	0.0502 (10)
H5	0.3516	0.2569	0.8268	0.060*
C6	0.6907 (6)	0.3509 (4)	0.7910 (4)	0.0369 (8)
C7	0.7123 (7)	0.5249 (5)	0.8604 (4)	0.0441 (9)
H7A	0.5645	0.5578	0.8801	0.053*
H7B	0.8083	0.5663	0.9446	0.053*
C8	0.9051 (7)	0.4468 (4)	0.6497 (4)	0.0429 (9)
H8A	1.0585	0.4388	0.6744	0.051*
H8B	0.9039	0.4590	0.5647	0.051*
O2	0.7873 (6)	0.8440 (4)	0.8963 (4)	0.0738 (11)
Br1	0.46555 (8)	0.29243 (5)	0.52887 (5)	0.05052 (17)
N1	0.8186 (6)	0.5743 (4)	0.7581 (3)	0.0443 (8)
O1	0.8850 (5)	0.2972 (3)	0.8292 (3)	0.0484 (7)
C9	1.2003 (8)	0.7824 (6)	0.8803 (5)	0.0592 (12)
H9A	1.2643	0.8899	0.9136	0.089*
H9B	1.2967	0.7208	0.8158	0.089*
H9C	1.1881	0.7529	0.9552	0.089*
O3	0.9632 (6)	0.7717 (4)	0.6764 (4)	0.0633 (9)
S1	0.92989 (17)	0.75291 (11)	0.80041 (11)	0.0423 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0378 (18)	0.034 (2)	0.0349 (19)	0.0078 (15)	0.0081 (15)	0.0151 (15)
C2	0.044 (2)	0.030 (2)	0.053 (2)	0.0081 (16)	0.0068 (18)	0.0124 (17)
C3	0.075 (3)	0.036 (2)	0.059 (3)	0.012 (2)	−0.007 (2)	0.022 (2)
C4	0.083 (3)	0.044 (3)	0.047 (2)	−0.008 (2)	0.002 (2)	0.024 (2)
C5	0.055 (2)	0.055 (3)	0.039 (2)	−0.003 (2)	0.0134 (19)	0.021 (2)
C6	0.0406 (19)	0.038 (2)	0.0328 (19)	0.0069 (15)	0.0043 (15)	0.0146 (16)
C7	0.052 (2)	0.036 (2)	0.041 (2)	0.0093 (17)	0.0121 (17)	0.0124 (17)
C8	0.052 (2)	0.031 (2)	0.043 (2)	0.0058 (17)	0.0165 (18)	0.0135 (17)
O2	0.066 (2)	0.0383 (19)	0.098 (3)	0.0125 (16)	0.012 (2)	0.0082 (18)
Br1	0.0549 (3)	0.0520 (3)	0.0448 (2)	0.01178 (18)	−0.00663 (17)	0.01939 (19)
N1	0.057 (2)	0.0296 (18)	0.0427 (19)	0.0044 (14)	0.0115 (15)	0.0122 (14)
O1	0.0595 (18)	0.0385 (16)	0.0455 (16)	0.0081 (13)	−0.0092 (13)	0.0159 (13)
C9	0.051 (2)	0.067 (3)	0.058 (3)	0.002 (2)	−0.011 (2)	0.027 (3)
O3	0.082 (2)	0.053 (2)	0.067 (2)	−0.0026 (16)	−0.0173 (18)	0.0413 (18)
S1	0.0465 (6)	0.0280 (5)	0.0509 (6)	0.0065 (4)	−0.0034 (4)	0.0148 (4)

C1—C8	1.519 (5)	C6—C7	1.507 (6)
C1—C2	1.538 (5)	C7—N1	1.482 (5)
C1—C6	1.558 (5)	C7—H7A	0.9700
C1—Br1	1.953 (4)	C7—H7B	0.9700
C2—C3	1.542 (6)	C8—N1	1.460 (5)
C2—H2A	0.9700	C8—H8A	0.9700
C2—H2B	0.9700	C8—H8B	0.9700
C3—O1	1.452 (5)	O2—S1	1.422 (4)
C3—C4	1.505 (7)	N1—S1	1.619 (3)
C3—H3	0.9800	C9—S1	1.749 (5)
C4—C5	1.317 (7)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—C6	1.506 (6)	C9—H9C	0.9600
C5—H5	0.9300	O3—S1	1.432 (3)
C6—O1	1.448 (5)
C8—C1—C2	118.5 (3)	C7—C6—C1	107.2 (3)
C8—C1—C6	101.3 (3)	N1—C7—C6	103.0 (3)
C2—C1—C6	102.7 (3)	N1—C7—H7A	111.2
C8—C1—Br1	108.7 (3)	C6—C7—H7A	111.2
C2—C1—Br1	112.9 (3)	N1—C7—H7B	111.2
C6—C1—Br1	112.0 (2)	C6—C7—H7B	111.2
C1—C2—C3	100.0 (3)	H7A—C7—H7B	109.1
C1—C2—H2A	111.8	N1—C8—C1	102.6 (3)
C3—C2—H2A	111.8	N1—C8—H8A	111.2
C1—C2—H2B	111.8	C1—C8—H8A	111.2
C3—C2—H2B	111.8	N1—C8—H8B	111.2
H2A—C2—H2B	109.5	C1—C8—H8B	111.2
O1—C3—C4	100.7 (4)	H8A—C8—H8B	109.2
O1—C3—C2	101.0 (3)	C8—N1—C7	111.4 (3)
C4—C3—C2	108.5 (4)	C8—N1—S1	121.6 (3)
O1—C3—H3	115.0	C7—N1—S1	120.8 (3)
C4—C3—H3	115.0	C6—O1—C3	95.6 (3)
C2—C3—H3	115.0	S1—C9—H9A	109.5
C5—C4—C3	107.0 (4)	S1—C9—H9B	109.5
C5—C4—H4	126.5	H9A—C9—H9B	109.5
C3—C4—H4	126.5	S1—C9—H9C	109.5
C4—C5—C6	105.1 (4)	H9A—C9—H9C	109.5
C4—C5—H5	127.4	H9B—C9—H9C	109.5
C6—C5—H5	127.4	O2—S1—O3	119.5 (2)
O1—C6—C5	101.4 (3)	O2—S1—N1	105.8 (2)
O1—C6—C7	111.1 (3)	O3—S1—N1	107.14 (19)
C5—C6—C7	125.8 (4)	O2—S1—C9	109.3 (3)
O1—C6—C1	97.9 (3)	O3—S1—C9	106.7 (2)
C5—C6—C1	109.8 (3)	N1—S1—C9	107.9 (2)
C8—C1—C2—C3	108.2 (4)	C5—C6—C7—N1	−143.5 (4)
C6—C1—C2—C3	−2.3 (4)	C1—C6—C7—N1	−12.1 (4)
Br1—C1—C2—C3	−123.1 (3)	C2—C1—C8—N1	−148.4 (4)
C1—C2—C3—O1	−35.0 (4)	C6—C1—C8—N1	−37.1 (4)
C1—C2—C3—C4	70.3 (4)	Br1—C1—C8—N1	80.9 (3)
O1—C3—C4—C5	31.9 (5)	C1—C8—N1—C7	32.5 (4)
C2—C3—C4—C5	−73.6 (5)	C1—C8—N1—S1	−175.0 (3)
C3—C4—C5—C6	0.7 (5)	C6—C7—N1—C8	−12.6 (5)
C4—C5—C6—O1	−33.4 (4)	C6—C7—N1—S1	−165.3 (3)
C4—C5—C6—C7	−160.2 (4)	C5—C6—O1—C3	51.1 (4)
C4—C5—C6—C1	69.4 (4)	C7—C6—O1—C3	−173.0 (3)
C8—C1—C6—O1	−84.1 (3)	C1—C6—O1—C3	−61.0 (3)
C2—C1—C6—O1	38.8 (3)	C4—C3—O1—C6	−50.1 (4)
Br1—C1—C6—O1	160.2 (2)	C2—C3—O1—C6	61.4 (4)
C8—C1—C6—C5	170.7 (3)	C8—N1—S1—O2	173.3 (4)
C2—C1—C6—C5	−66.4 (4)	C7—N1—S1—O2	−36.8 (4)
Br1—C1—C6—C5	55.0 (4)	C8—N1—S1—O3	44.7 (4)
C8—C1—C6—C7	31.0 (4)	C7—N1—S1—O3	−165.3 (3)
C2—C1—C6—C7	153.9 (3)	C8—N1—S1—C9	−69.8 (4)
Br1—C1—C6—C7	−84.7 (3)	C7—N1—S1—C9	80.1 (4)
O1—C6—C7—N1	93.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.96	2.59	3.385 (7)	140
C9—H9C···O1ii	0.96	2.59	3.540 (6)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.96	2.59	3.385 (7)	140
C9—H9C⋯O1ii	0.96	2.59	3.540 (6)	172

Symmetry codes: (i) ; (ii) .