(1RS,4SR)-3-Dichloro-methyl-ene-1,4-dimethyl-2-oxabicyclo-[2.2.2]oct-5-ene.

X-ray crystallography was used to confirm the structure of the enantio-enriched title compound, C(10)H(12)Cl(2)O, a bicylic enol ether. A bridged boat-like structure is adopted and the dichloro-methyl-ene C atom is positioned significantly removed from the core bicyclic unit. In the crystal structure, mol-ecules pack to form sheets approximately perpendicular to the a and c axes.

Related literature

For related literature, see: Yamabe et al. (1996 ▶); Machiguchi et al. (1999 ▶); Khanjin et al. (1999 ▶); Ussing et al. (2006 ▶); Robertson & Fowler (2006 ▶).

Experimental

Crystal data

C10H12Cl2O

M = 219.11

Monoclinic,

a = 9.3365 (1) Å

b = 9.6327 (2) Å

c = 11.4259 (2) Å

β = 92.7347 (11)°

V = 1026.43 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 150 K

0.44 × 0.32 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.83, T max = 0.90

4320 measured reflections

2321 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.01

2321 reflections

118 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: Görbitz (1999 ▶) and DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017248/lh2637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017248/lh2637Isup2.hkl

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

C10H12Cl2O1	F000 = 456
Mr = 219.11	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15784 reflections
a = 9.3365 (1) Å	θ = 5–27º
b = 9.6327 (2) Å	µ = 0.59 mm−1
c = 11.4259 (2) Å	T = 150 K
β = 92.7347 (11)º	Prism, colourless
V = 1026.43 (3) Å3	0.44 × 0.32 × 0.18 mm
Z = 4

Nonius KappaCCD diffractometer	2094 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 150 K	θmax = 27.4º
ω scans	θmin = 5.1º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.83, Tmax = 0.90	k = −12→12
4320 measured reflections	l = −14→14
2321 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.093	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.05P)2 + 0.71P], where P = [max(Fo2,0) + 2Fc2]/3
S = 1.01	(Δ/σ)max = 0.001
2321 reflections	Δρmax = 0.36 e Å−3
118 parameters	Δρmin = −0.38 e Å−3
2 restraints	Extinction correction: None

	x	y	z	Uiso*/Ueq
C1	0.02322 (16)	0.72676 (17)	0.56170 (14)	0.0234
O2	0.12271 (11)	0.62312 (12)	0.61475 (10)	0.0217
C3	0.26458 (15)	0.64956 (16)	0.59821 (13)	0.0192
C4	0.28716 (17)	0.77747 (17)	0.52291 (14)	0.0230
C5	0.21390 (19)	0.89526 (18)	0.58719 (15)	0.0293
C6	0.07027 (19)	0.86685 (17)	0.60962 (15)	0.0274
C7	0.04601 (18)	0.72396 (18)	0.43089 (14)	0.0280
C8	0.19575 (18)	0.75082 (18)	0.40893 (14)	0.0267
C9	−0.12456 (17)	0.6806 (2)	0.59357 (17)	0.0326
C10	0.44060 (19)	0.8143 (2)	0.49372 (17)	0.0339
C11	0.35800 (16)	0.56064 (17)	0.64983 (14)	0.0215
Cl12	0.29697 (4)	0.42007 (4)	0.72783 (4)	0.0295
Cl13	0.54194 (4)	0.56859 (5)	0.64989 (4)	0.0320
H51	0.2631	0.9775	0.6123	0.0403*
H61	0.0073	0.9265	0.6509	0.0362*
H71	−0.0214	0.7925	0.3907	0.0397*
H72	0.0158	0.6344	0.3998	0.0386*
H81	0.1990	0.8293	0.3587	0.0379*
H82	0.2347	0.6712	0.3675	0.0381*
H91	−0.1917	0.7492	0.5652	0.0477*
H92	−0.1261	0.6724	0.6804	0.0498*
H93	−0.1529	0.5941	0.5590	0.0483*
H101	0.4319	0.8976	0.4440	0.0529*
H102	0.5032	0.8374	0.5608	0.0543*
H103	0.4864	0.7409	0.4472	0.0531*

	U11	U22	U33	U12	U13	U23
C1	0.0213 (7)	0.0229 (7)	0.0254 (8)	0.0045 (6)	−0.0044 (6)	−0.0009 (6)
O2	0.0175 (5)	0.0225 (6)	0.0251 (5)	0.0016 (4)	0.0005 (4)	0.0041 (4)
C3	0.0188 (7)	0.0205 (7)	0.0183 (7)	−0.0023 (5)	0.0005 (5)	−0.0019 (6)
C4	0.0257 (7)	0.0220 (7)	0.0209 (7)	−0.0043 (6)	−0.0022 (5)	0.0018 (6)
C5	0.0373 (8)	0.0221 (8)	0.0275 (8)	0.0009 (7)	−0.0073 (7)	−0.0031 (7)
C6	0.0339 (8)	0.0229 (8)	0.0251 (8)	0.0055 (7)	−0.0030 (6)	−0.0032 (6)
C7	0.0347 (8)	0.0264 (8)	0.0223 (8)	0.0014 (7)	−0.0067 (6)	−0.0013 (6)
C8	0.0352 (8)	0.0268 (8)	0.0178 (7)	−0.0025 (7)	−0.0026 (6)	0.0010 (6)
C9	0.0212 (8)	0.0328 (9)	0.0435 (10)	0.0028 (7)	−0.0005 (7)	−0.0031 (8)
C10	0.0309 (9)	0.0345 (10)	0.0360 (9)	−0.0126 (7)	−0.0013 (7)	0.0072 (8)
C11	0.0189 (7)	0.0234 (7)	0.0222 (7)	−0.0011 (6)	0.0001 (5)	0.0004 (6)
Cl12	0.0292 (2)	0.0261 (2)	0.0329 (2)	−0.00012 (15)	−0.00257 (16)	0.01006 (16)
Cl13	0.0183 (2)	0.0372 (3)	0.0401 (3)	0.00107 (15)	−0.00273 (16)	0.00256 (18)

C1—O2	1.4741 (18)	C7—C8	1.455 (2)
C1—C6	1.514 (2)	C7—H71	1.008
C1—C7	1.520 (2)	C7—H72	0.970
C1—C9	1.511 (2)	C8—H81	0.950
O2—C3	1.3707 (17)	C8—H82	0.980
C3—C4	1.523 (2)	C9—H91	0.957
C3—C11	1.339 (2)	C9—H92	0.996
C4—C5	1.531 (2)	C9—H93	0.954
C4—C8	1.544 (2)	C10—H101	0.985
C4—C10	1.528 (2)	C10—H102	0.968
C5—C6	1.404 (3)	C10—H103	0.993
C5—H51	0.953	C11—Cl12	1.7324 (16)
C6—H61	0.962	C11—Cl13	1.7190 (15)
O2—C1—C6	106.78 (12)	C1—C7—H72	108.9
O2—C1—C7	106.10 (12)	C8—C7—H72	111.1
C6—C1—C7	108.65 (14)	H71—C7—H72	104.6
O2—C1—C9	105.44 (13)	C4—C8—C7	112.39 (13)
C6—C1—C9	115.34 (14)	C4—C8—H81	110.2
C7—C1—C9	113.84 (14)	C7—C8—H81	107.7
C1—O2—C3	114.30 (12)	C4—C8—H82	109.5
O2—C3—C4	112.89 (12)	C7—C8—H82	109.0
O2—C3—C11	115.71 (13)	H81—C8—H82	107.9
C4—C3—C11	131.40 (14)	C1—C9—H91	107.8
C3—C4—C5	104.57 (13)	C1—C9—H92	108.7
C3—C4—C8	104.84 (12)	H91—C9—H92	110.5
C5—C4—C8	106.63 (13)	C1—C9—H93	113.3
C3—C4—C10	117.88 (14)	H91—C9—H93	107.4
C5—C4—C10	112.19 (14)	H92—C9—H93	109.1
C8—C4—C10	109.92 (13)	C4—C10—H101	105.3
C4—C5—C6	113.31 (14)	C4—C10—H102	114.7
C4—C5—H51	122.7	H101—C10—H102	107.4
C6—C5—H51	123.9	C4—C10—H103	112.5
C1—C6—C5	111.77 (14)	H101—C10—H103	107.3
C1—C6—H61	122.4	H102—C10—H103	109.2
C5—C6—H61	125.8	C3—C11—Cl12	120.21 (12)
C1—C7—C8	110.31 (13)	C3—C11—Cl13	126.97 (12)
C1—C7—H71	108.8	Cl12—C11—Cl13	112.82 (9)
C8—C7—H71	112.9