6-Bromo-8-thia-1,4-epoxy­bicyclo­[4.3.0]non-2-ene

In the title compound, C₈H₉BrOS, the mol­ecules are linked only by weak van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.006 Å
• R factor = 0.039
• wR factor = 0.093
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

6-Bromo-8-Thio-1,4-Epoxybicyclo[4.3.0]non-2-ene

Crystal data

C8H9BrOS	Z = 2
Mr = 233.12	F(000) = 232
Triclinic, P1	Dx = 1.784 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6508 (10) Å	Cell parameters from 4150 reflections
b = 7.9576 (12) Å	θ = 2.5–28.0°
c = 8.4012 (12) Å	µ = 4.91 mm^−1
α = 81.030 (12)°	T = 296 K
β = 88.572 (12)°	Prism, colourless
γ = 81.179 (12)°	0.26 × 0.20 × 0.16 mm
V = 434.00 (11) Å^3

Data collection

STOE IPDS-II diffractometer	1704 independent reflections
Radiation source: fine-focus sealed tube	1436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
ω rotation method scans	h = −8→8
Absorption correction: integration X-RED (Stoe & Cie, 2002)	k = −9→9
Tmin = 0.371, Tmax = 0.631	l = −10→10
5151 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.022P] where P = (Fo^2 + 2Fc^2)/3
1704 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9614 (6)	0.2614 (5)	0.4466 (5)	0.0529 (9)
H1A	1.0560	0.3429	0.4469	0.063*
H1B	1.0377	0.1460	0.4634	0.063*
C2	0.8496 (5)	0.2944 (4)	0.2883 (5)	0.0434 (8)
C3	0.9471 (7)	0.1924 (5)	0.1584 (6)	0.0592 (11)
H3A	1.0809	0.1308	0.1904	0.071*
H3B	0.9568	0.2659	0.0558	0.071*
C4	0.7900 (8)	0.0676 (6)	0.1528 (6)	0.0626 (12)
H4	0.8423	−0.0386	0.1103	0.075*
C5	0.6025 (8)	0.1721 (7)	0.0691 (6)	0.0697 (12)
H5	0.5585	0.1693	−0.0346	0.084*
C6	0.5143 (7)	0.2677 (6)	0.1728 (6)	0.0593 (10)
H6	0.3955	0.3468	0.1576	0.071*
C7	0.6458 (5)	0.2226 (4)	0.3215 (5)	0.0437 (8)
C8	0.5621 (6)	0.2530 (5)	0.4841 (5)	0.0527 (9)
H8A	0.5022	0.1545	0.5355	0.063*
H8B	0.4579	0.3536	0.4731	0.063*
O1	0.7252 (4)	0.0438 (3)	0.3181 (4)	0.0529 (7)
S1	0.7737 (2)	0.28576 (17)	0.60491 (14)	0.0662 (3)
Br1	0.79531 (7)	0.54368 (5)	0.21367 (5)	0.05661 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.043 (2)	0.051 (2)	0.062 (3)	−0.0052 (17)	−0.0083 (17)	−0.0003 (18)
C2	0.0412 (19)	0.0381 (16)	0.050 (2)	−0.0086 (15)	0.0045 (15)	−0.0006 (14)
C3	0.060 (3)	0.056 (2)	0.062 (3)	−0.009 (2)	0.020 (2)	−0.0131 (19)
C4	0.082 (3)	0.051 (2)	0.060 (3)	−0.018 (2)	0.024 (2)	−0.0216 (19)
C5	0.080 (3)	0.079 (3)	0.058 (3)	−0.028 (3)	−0.008 (2)	−0.016 (2)
C6	0.051 (2)	0.061 (2)	0.066 (3)	−0.013 (2)	−0.0135 (19)	−0.004 (2)
C7	0.0388 (19)	0.0388 (17)	0.053 (2)	−0.0079 (15)	0.0041 (15)	−0.0033 (15)
C8	0.049 (2)	0.051 (2)	0.060 (3)	−0.0152 (18)	0.0136 (18)	−0.0085 (17)
O1	0.0587 (16)	0.0383 (13)	0.0615 (17)	−0.0095 (12)	0.0106 (13)	−0.0068 (11)
S1	0.0740 (8)	0.0793 (7)	0.0440 (6)	−0.0123 (6)	−0.0005 (5)	−0.0052 (5)
Br1	0.0706 (3)	0.0409 (2)	0.0568 (3)	−0.01534 (17)	0.00089 (18)	0.00409 (15)

Geometric parameters (Å, º)

C1—C2	1.508 (6)	C4—C5	1.512 (8)
C1—S1	1.813 (4)	C4—H4	0.9800
C1—H1A	0.9700	C5—C6	1.314 (7)
C1—H1B	0.9700	C5—H5	0.9300
C2—C3	1.533 (5)	C6—C7	1.508 (6)
C2—C7	1.552 (5)	C6—H6	0.9300
C2—Br1	1.965 (3)	C7—O1	1.444 (4)
C3—C4	1.554 (6)	C7—C8	1.502 (5)
C3—H3A	0.9700	C8—S1	1.829 (4)
C3—H3B	0.9700	C8—H8A	0.9700
C4—O1	1.436 (5)	C8—H8B	0.9700
C2—C1—S1	107.7 (3)	C5—C4—H4	115.1
C2—C1—H1A	110.2	C3—C4—H4	115.1
S1—C1—H1A	110.2	C6—C5—C4	105.9 (4)
C2—C1—H1B	110.2	C6—C5—H5	127.1
S1—C1—H1B	110.2	C4—C5—H5	127.1
H1A—C1—H1B	108.5	C5—C6—C7	105.7 (4)
C1—C2—C3	115.5 (3)	C5—C6—H6	127.1
C1—C2—C7	106.5 (3)	C7—C6—H6	127.1
C3—C2—C7	102.3 (3)	O1—C7—C8	112.3 (3)
C1—C2—Br1	109.1 (3)	O1—C7—C6	102.1 (3)
C3—C2—Br1	113.0 (3)	C8—C7—C6	121.4 (3)
C7—C2—Br1	109.9 (2)	O1—C7—C2	97.3 (3)
C2—C3—C4	100.0 (3)	C8—C7—C2	111.0 (3)
C2—C3—H3A	111.8	C6—C7—C2	109.9 (3)
C4—C3—H3A	111.8	C7—C8—S1	107.4 (3)
C2—C3—H3B	111.8	C7—C8—H8A	110.2
C4—C3—H3B	111.8	S1—C8—H8A	110.2
H3A—C3—H3B	109.5	C7—C8—H8B	110.2
O1—C4—C5	102.0 (4)	S1—C8—H8B	110.2
O1—C4—C3	100.9 (3)	H8A—C8—H8B	108.5
C5—C4—C3	107.1 (4)	C4—O1—C7	95.7 (3)
O1—C4—H4	115.1	C1—S1—C8	94.58 (18)
S1—C1—C2—C3	−148.0 (3)	C1—C2—C7—C8	36.9 (4)
S1—C1—C2—C7	−35.2 (3)	C3—C2—C7—C8	158.5 (3)
S1—C1—C2—Br1	83.5 (3)	Br1—C2—C7—C8	−81.2 (3)
C1—C2—C3—C4	110.1 (4)	C1—C2—C7—C6	173.9 (3)
C7—C2—C3—C4	−5.2 (4)	C3—C2—C7—C6	−64.5 (4)
Br1—C2—C3—C4	−123.3 (3)	Br1—C2—C7—C6	55.8 (4)
C2—C3—C4—O1	−33.0 (4)	O1—C7—C8—S1	86.5 (3)
C2—C3—C4—C5	73.3 (4)	C6—C7—C8—S1	−152.5 (3)
O1—C4—C5—C6	32.3 (5)	C2—C7—C8—S1	−21.2 (4)
C3—C4—C5—C6	−73.2 (5)	C5—C4—O1—C7	−49.4 (4)
C4—C5—C6—C7	−0.3 (5)	C3—C4—O1—C7	60.9 (4)
C5—C6—C7—O1	−31.6 (4)	C8—C7—O1—C4	−179.1 (3)
C5—C6—C7—C8	−157.4 (4)	C6—C7—O1—C4	49.4 (4)
C5—C6—C7—C2	70.8 (4)	C2—C7—O1—C4	−62.8 (3)
C1—C2—C7—O1	−80.4 (3)	C2—C1—S1—C8	20.9 (3)
C3—C2—C7—O1	41.3 (3)	C7—C8—S1—C1	0.3 (3)
Br1—C2—C7—O1	161.6 (2)