(3aR,6S,7aR)-7a-Bromo-2-methyl­sulfonyl-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­oxy­isoindole

Temel, E.; Demircan, A.; Arslan, H.; Büyükgüngör, O.

doi:10.1107/S1600536811015959

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1304-o1305

doi:10.1107/S1600536811015959

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(3aR,6S,7aR)-7a-Bromo-2-methylsulfonyl-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

Ersin Temel,^a Aydın Demircan,^b Hakan Arslan ^c,^d ^* and Orhan Büyükgüngör ^a

^aDepartment of Physics, Arts and Sciences Faculty, Ondokuz Mayıs University, Samsun, TR 55139, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Nigde University, Nigde, TR 51240, Turkey, ^cDepartment of Chemistry, Emory University, Atlanta, GA 30322, USA, and ^dDepartment of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 26 April 2011; accepted 27 April 2011; online 7 May 2011)

In the title compound, C₉H₁₂BrNO₃S, the two tetrahydrofuran 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 intermolecular C—H⋯O hydrogen bonds link the molecules into R²₂(8) and R²₂(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_r = 294.17
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.107
S = 1.10
2293 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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) -x+2, -y+2, -z+2; (ii) -x+2, -y+1, -z+2.

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 ).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811015959/hg5029Isup3.cml

checkCIF report

Comment top

Sulfonamides are one of the most important groups of compounds for the medical purposes (Kleemann et al., 1999). They have mostly been applied for the treatment of bacterial infection (Cremlyn, 1996). Sulfonamide is not only an early class of antibiotics, also, has showed different functionality such as a protease inhibitor amprenavir, the analgesic celecoxib, sildenafil for erectile dysfunction, and the antimigraine agent sumatriptan. The most sulfonamides have been synthesized from a reaction between a sulfonyl chloride and ammonia or primary or secondary amines or via related transformations (Anderson, 1979).

Several thermal intramolecular Diels Alder reaction of furans (IMDAF) cycloadditon were performed including a nitrogen linked side chain of furan and already reported by Demircan and his co-workers (Demircan and Parsons, 2002; Arslan et al., 2008). We would like to report here a newly synthesized sulfonamide, I.

In continuation of our interest, 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 (Greene, 1981; Choony et al., 1997). This facile, versatile and environmentally friendly reaction was accomplished in aqueous condition and stirred for two days at 372 K.

The molecular structure of the title compound, I, is shown in Fig. 1. A l l bond lengths show normal values (Allen et al., 1987). In addition, the C—Br bond distance, 1.953 (4) Å, is not significantly different from the value reported for C—Br single bond (1.961 (3) Å; Koşar et al., 2006). The six membered ring, C1—C6, is in a boat conformation with puckering parameter Q = 0.933 (5) Å, θ = 89.1 (3) °, ϕ = 119.1 (3) °. The tetrahydrofuran, O1/C3–C6, and bromo-attached tetrahydrofuran, O1/C3/C2/C1/C6, rings adopt envelope conformations, and the puckering parameter Q values are 0.517 (5) and 0.607 (4) ° Å, respectively (Cremer & Pople, 1975). The pyrrolidine ring, N1/C7/C6/C1/C8, adopts half chair conformation, and the puckering parameter Q = 0.368 (4) Å and ϕ = 304.8 (7) °, (Cremer & Pople, 1975).

Fig. 2 shows the packing of the molecules in the unit cell. The crystal packing of (I) is stabilized by intermolecular C9—H9A···O2 and C9—H9C···O1 interactions (Table 1). The methyl group in the reference molecule at (x, y, z) acts as double hydrogen bond donor, via H9A and H9C, to atoms O2 in the molecule at (-x + 2, -y + 2, -z + 2) and O1 in the molecule at (-x + 2, -y + 1, -z + 2), so forming successive R²₂(8) and R²₂(14) rings running parallel to the [010] direction (Bernstein et al., 1995).

Related literature top

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 pu ckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

N-(2-bromoprop-2-en-1-yl)-N-(2-furylmethyl)methanesulfonamide, II, (1 g, 3.4 mmol) was stirred in water (25 ml) at 372 K for two days (Fig. 3). The reaction was stirred and monitored by thin layer chromatography until no further cycloadditon observed. The mixture was poured into ethylacetate (25 ml) and aqueous phase was washed with excess of ethyl acetate (2 x 25 ml). Combined organic phases was dried on magnesium sulfate and filtered off. The solvent was then removed under reduced pressure. The residue was subjected to flash column chromatography to afford the title compound, (3aR,6S,7aR)-7a-bromo-2-(methylsulfonyl)-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole, I, with 0.74 g, 74% yield as light brown crystals.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of the title compound, showing the formation of R²₂(8) and R²₂(14) rings along [010]. Hydrogen bonds are indicated by dashed lines. (Symmetry codes as in Table 1)
	Fig. 3. Synthesis of the title compound.

(3aR,6S,7aR)-7a-Bromo-2-methylsulfonyl-1,2,3,6,7,7a- hexahydro-3a,6-epoxyisoindole top

Crystal data top

C₉H₁₂BrNO₃S	Z = 2
M_r = 294.17	F(000) = 296
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0452P)² + 0.3277P] where P = (F_o² + 2F_c²)/3
2293 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₉H₁₂BrNO₃S	γ = 97.812 (9)°
M_r = 294.17	V = 553.46 (10) Å³
Triclinic, P1	Z = 2
a = 5.9478 (7) Å	Mo Kα radiation
b = 9.5869 (10) Å	µ = 3.89 mm⁻¹
c = 10.7775 (11) Å	T = 296 K
α = 114.307 (8)°	0.38 × 0.23 × 0.08 mm
β = 90.481 (9)°

Data collection top

Stoe IPDS 2 diffractometer	2293 independent reflections
Absorption correction: integration (X-RED; Stoe & Cie, 2001)	1920 reflections with I > 2σ(I)
T_min = 0.223, T_max = 0.682	R_int = 0.082
8163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.10	Δρ_max = 0.86 e Å⁻³
2293 reflections	Δρ_min = −0.44 e Å⁻³
137 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+2; (ii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₉H₁₂BrNO₃S
M_r	294.17
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.9478 (7), 9.5869 (10), 10.7775 (11)
α, β, γ (°)	114.307 (8), 90.481 (9), 97.812 (9)
V (Å³)	553.46 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.89
Crystal size (mm)	0.38 × 0.23 × 0.08

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED; Stoe & Cie, 2001)
T_min, T_max	0.223, 0.682
No. of measured, independent and observed [I > 2σ(I)] reflections	8163, 2293, 1920
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.107, 1.10
No. of reflections	2293
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.44

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+2; (ii) −x+2, −y+1, −z+2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs 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 (TÜBİTAK) for the financial support of this work (PN: 107 T831).

References

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Volume 67| Part 6| June 2011| Pages o1304-o1305

doi:10.1107/S1600536811015959

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3aR,6S,7aR)-7a-Bromo-2-methyl­sulfonyl-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­­oxy­iso­indole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aR,6S,7aR)-7a-Bromo-2-methylsulfonyl-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole