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

In the structure of the title compound, C₈H₉ClOS, the six-membered ring has a boat conformation and the S-containing five-membered ring has an envelope conformation. The mol­ecules are linked only by weak van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.127
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT320_ALERT_2_C Check Hybridisation of  C3     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Crystal data

C8H9ClOS	Z = 2
Mr = 188.66	F(000) = 196
Triclinic, P1	Dx = 1.507 Mg m^−3
a = 6.651 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.971 (3) Å	Cell parameters from 5795 reflections
c = 8.048 (3) Å	θ = 2.6–27.9°
α = 80.33 (3)°	µ = 0.64 mm^−1
β = 89.07 (3)°	T = 293 K
γ = 81.43 (3)°	Prism, colorless
V = 415.9 (3) Å^3	0.43 × 0.34 × 0.17 mm

Data collection

Stoe IPDS-2 diffractometer	1624 independent reflections
Radiation source: fine-focus sealed tube	1330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.769, Tmax = 0.896	l = −9→9
3731 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.0767P] where P = (Fo^2 + 2Fc^2)/3
1624 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.50 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	0.1559 (4)	0.1993 (3)	0.7146 (3)	0.0389 (5)
C2	0.0671 (5)	0.2975 (4)	0.8531 (4)	0.0535 (7)
C3	0.2251 (5)	0.4229 (4)	0.8537 (4)	0.0551 (7)
C4	0.4166 (5)	0.3190 (5)	0.9338 (4)	0.0617 (8)
C5	0.4960 (4)	0.2269 (4)	0.8226 (4)	0.0518 (7)
C6	0.3569 (3)	0.2748 (3)	0.6707 (3)	0.0386 (5)
C7	0.4288 (4)	0.2466 (4)	0.4992 (4)	0.0492 (6)
C8	0.0336 (4)	0.2329 (4)	0.5525 (4)	0.0461 (6)
O1	0.2791 (3)	0.4507 (2)	0.6782 (2)	0.0467 (5)
S1	0.21149 (13)	0.21040 (11)	0.38192 (9)	0.0601 (3)
Cl1	0.20835 (11)	−0.03010 (8)	0.78573 (9)	0.0523 (2)
H1	0.482 (6)	0.345 (5)	0.446 (5)	0.070 (10)*
H2	0.053 (6)	0.226 (5)	0.964 (6)	0.080 (12)*
H3	0.162 (6)	0.530 (5)	0.876 (5)	0.075 (11)*
H4	−0.058 (5)	0.143 (4)	0.552 (4)	0.050 (8)*
H5	0.536 (5)	0.148 (4)	0.510 (4)	0.056 (9)*
H6	−0.070 (6)	0.354 (4)	0.823 (4)	0.052 (8)*
H7	−0.038 (5)	0.347 (4)	0.532 (4)	0.047 (8)*
H8	0.617 (7)	0.144 (5)	0.838 (5)	0.078 (12)*
H10	0.460 (6)	0.314 (4)	1.060 (5)	0.065 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0338 (11)	0.0347 (11)	0.0471 (14)	−0.0095 (9)	0.0042 (9)	−0.0006 (10)
C2	0.0487 (16)	0.0581 (16)	0.0572 (18)	−0.0151 (13)	0.0139 (13)	−0.0146 (14)
C3	0.0606 (17)	0.0544 (17)	0.0565 (18)	−0.0145 (13)	0.0122 (14)	−0.0223 (14)
C4	0.0664 (19)	0.0711 (19)	0.0542 (18)	−0.0264 (15)	−0.0059 (15)	−0.0141 (15)
C5	0.0406 (14)	0.0589 (17)	0.0578 (17)	−0.0157 (12)	−0.0078 (12)	−0.0069 (13)
C6	0.0334 (11)	0.0361 (11)	0.0464 (14)	−0.0104 (9)	0.0047 (10)	−0.0033 (10)
C7	0.0480 (14)	0.0539 (15)	0.0499 (16)	−0.0191 (12)	0.0126 (12)	−0.0112 (13)
C8	0.0401 (13)	0.0472 (14)	0.0488 (15)	−0.0074 (11)	−0.0040 (10)	−0.0006 (11)
O1	0.0499 (10)	0.0361 (9)	0.0551 (12)	−0.0113 (7)	0.0075 (8)	−0.0072 (8)
S1	0.0642 (5)	0.0781 (6)	0.0397 (4)	−0.0195 (4)	−0.0008 (3)	−0.0067 (3)
Cl1	0.0603 (4)	0.0406 (4)	0.0541 (4)	−0.0169 (3)	−0.0030 (3)	0.0062 (3)

Geometric parameters (Å, º)

C1—C8	1.512 (4)	C4—H10	1.06 (4)
C1—C2	1.529 (4)	C5—C6	1.507 (4)
C1—C6	1.558 (3)	C5—H8	0.96 (4)
C1—Cl1	1.805 (2)	C6—O1	1.432 (3)
C2—C3	1.555 (4)	C6—C7	1.495 (4)
C2—H2	0.98 (4)	C7—S1	1.823 (3)
C2—H6	0.97 (4)	C7—H1	0.94 (4)
C3—O1	1.441 (4)	C7—H5	0.97 (3)
C3—C4	1.502 (5)	C8—S1	1.812 (3)
C3—H3	0.94 (4)	C8—H4	1.01 (3)
C4—C5	1.307 (5)	C8—H7	0.95 (3)
C8—C1—C2	115.8 (2)	C4—C5—H8	126 (3)
C8—C1—C6	106.2 (2)	C6—C5—H8	128 (3)
C2—C1—C6	102.5 (2)	O1—C6—C7	113.2 (2)
C8—C1—Cl1	108.65 (19)	O1—C6—C5	101.8 (2)
C2—C1—Cl1	112.67 (19)	C7—C6—C5	121.8 (2)
C6—C1—Cl1	110.64 (16)	O1—C6—C1	97.47 (18)
C1—C2—C3	99.9 (2)	C7—C6—C1	110.9 (2)
C1—C2—H2	115 (2)	C5—C6—C1	108.6 (2)
C3—C2—H2	113 (3)	C6—C7—S1	107.76 (19)
C1—C2—H6	110 (2)	C6—C7—H1	109 (2)
C3—C2—H6	114.0 (19)	S1—C7—H1	111 (2)
H2—C2—H6	104 (3)	C6—C7—H5	109 (2)
O1—C3—C4	101.8 (2)	S1—C7—H5	111 (2)
O1—C3—C2	100.8 (2)	H1—C7—H5	109 (3)
C4—C3—C2	107.3 (3)	C1—C8—S1	107.43 (18)
O1—C3—H3	106 (3)	C1—C8—H4	110.8 (18)
C4—C3—H3	127 (3)	S1—C8—H4	106.6 (18)
C2—C3—H3	111 (2)	C1—C8—H7	111 (2)
C5—C4—C3	105.7 (3)	S1—C8—H7	107.7 (18)
C5—C4—H10	129 (2)	H4—C8—H7	113 (3)
C3—C4—H10	124 (2)	C6—O1—C3	96.1 (2)
C4—C5—C6	106.3 (3)	C8—S1—C7	94.61 (13)
C8—C1—C2—C3	−110.7 (3)	C8—C1—C6—C5	−173.5 (2)
C6—C1—C2—C3	4.4 (3)	C2—C1—C6—C5	64.6 (3)
Cl1—C1—C2—C3	123.3 (2)	Cl1—C1—C6—C5	−55.7 (3)
C1—C2—C3—O1	33.1 (3)	O1—C6—C7—S1	−87.4 (2)
C1—C2—C3—C4	−73.0 (3)	C5—C6—C7—S1	150.7 (2)
O1—C3—C4—C5	−32.4 (3)	C1—C6—C7—S1	21.0 (3)
C2—C3—C4—C5	72.9 (3)	C2—C1—C8—S1	148.7 (2)
C3—C4—C5—C6	1.0 (3)	C6—C1—C8—S1	35.7 (2)
C4—C5—C6—O1	30.9 (3)	Cl1—C1—C8—S1	−83.32 (18)
C4—C5—C6—C7	158.1 (3)	C7—C6—O1—C3	178.9 (2)
C4—C5—C6—C1	−71.2 (3)	C5—C6—O1—C3	−48.7 (2)
C8—C1—C6—O1	81.3 (2)	C1—C6—O1—C3	62.2 (2)
C2—C1—C6—O1	−40.6 (2)	C4—C3—O1—C6	49.5 (2)
Cl1—C1—C6—O1	−160.94 (17)	C2—C3—O1—C6	−60.9 (2)
C8—C1—C6—C7	−37.1 (3)	C1—C8—S1—C7	−21.6 (2)
C2—C1—C6—C7	−159.0 (2)	C6—C7—S1—C8	0.3 (2)
Cl1—C1—C6—C7	80.6 (2)