rac-(3aR,6aR)-(E)-Methyl 2-(3a-methyl-perhydro-furo[3,2-b]furan-2-yl-idene)acetate.

The constitution and relative configuration at the stereogenic centres and stereochemistry of the C-C double bond formed during Pd(II)-catalysed domino reaction was established by X-ray analysis of the title compound, C(10)H(14)O(4). The asymmetric unit contains two mol-ecules.

Related literature

The title compound was prepared from 4-methyl­pent-4-en-1,3-diol (Breit & Zahn, 2001 ▶) by a modified procedure for carbonyl­ation of alkene-3-ol (Semmelhack & Epa, 1993 ▶).

Experimental

Crystal data

C10H14O4

M = 198.21

Monoclinic,

a = 12.159 (1) Å

b = 5.8100 (3) Å

c = 28.509 (1) Å

β = 101.51 (1)°

V = 1973.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.84 × 0.36 × 0.12 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010 ▶); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.941, T max = 0.988

59312 measured reflections

4033 independent reflections

3571 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.05

4025 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032101/bv2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032101/bv2142Isup2.hkl

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

C10H14O4	F(000) = 848
Mr = 198.21	Dx = 1.334 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 35551 reflections
a = 12.159 (1) Å	θ = 3.6–29.5°
b = 5.8100 (3) Å	µ = 0.10 mm−1
c = 28.509 (1) Å	T = 293 K
β = 101.51 (1)°	Block, colorless
V = 1973.5 (2) Å3	0.84 × 0.36 × 0.12 mm
Z = 8

Oxford Diffraction Gemini R CCD diffractometer	4033 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3571 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.4340 pixels mm-1	θmax = 26.4°, θmin = 3.6°
Rotation method data acquisition using ω and φ scans	h = −15→15
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −7→7
Tmin = 0.941, Tmax = 0.988	l = −35→35
59312 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0375P)2 + 1.2579P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4025 reflections	Δρmax = 0.32 e Å−3
254 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.62 (release 16-03-2010 CrysAlis171 .NET) (compiled Mar 16 2010,16:26:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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.independent reflections were 4033, 7 inconsistent equivalents, 4025 were used in the refinement

	x	y	z	Uiso*/Ueq
C2	0.35925 (10)	0.2368 (2)	0.34753 (4)	0.0173 (3)
C3	0.35197 (10)	0.4998 (2)	0.34359 (4)	0.0174 (3)
H3A	0.4074	0.5638	0.3265	0.021*
C4	0.36899 (10)	0.5847 (2)	0.39470 (4)	0.0195 (3)
H4B	0.3319	0.7311	0.3967	0.023*
H4A	0.4481	0.5997	0.4089	0.023*
C5	0.31418 (11)	0.3932 (2)	0.41825 (4)	0.0212 (3)
H5B	0.3475	0.3829	0.4521	0.025*
H5A	0.2344	0.4214	0.4149	0.025*
C7	0.18323 (10)	0.3541 (2)	0.30141 (4)	0.0177 (3)
C8	0.26323 (10)	0.1555 (2)	0.30792 (4)	0.0192 (3)
H8B	0.2897	0.1237	0.2786	0.023*
H8A	0.2282	0.0180	0.3175	0.023*
C9	0.47359 (10)	0.1376 (2)	0.34558 (5)	0.0212 (3)
H9C	0.4713	−0.0270	0.3484	0.025*
H9B	0.5286	0.1989	0.3715	0.025*
H9A	0.4933	0.1779	0.3157	0.025*
C10	0.07393 (10)	0.3673 (2)	0.28094 (4)	0.0197 (3)
H10A	0.0379	0.5089	0.2799	0.024*
C11	0.01014 (10)	0.1674 (2)	0.26033 (4)	0.0189 (3)
C14	−0.16945 (12)	0.0392 (3)	0.22261 (6)	0.0306 (3)
H14C	−0.2446	0.0946	0.2118	0.037*
H14B	−0.1693	−0.0791	0.2461	0.037*
H14A	−0.1416	−0.0225	0.1960	0.037*
C16	0.86595 (10)	0.9608 (2)	0.38508 (4)	0.0190 (3)
C17	0.96259 (11)	1.0068 (2)	0.42723 (4)	0.0200 (3)
H17A	0.9589	1.1601	0.4412	0.024*
C18	1.06680 (11)	0.9721 (2)	0.40691 (5)	0.0247 (3)
H18B	1.1303	0.9277	0.4316	0.030*
H18A	1.0857	1.1098	0.3910	0.030*
C19	1.03089 (11)	0.7781 (3)	0.37159 (5)	0.0255 (3)
H19B	1.0714	0.7855	0.3456	0.031*
H19A	1.0452	0.6299	0.3873	0.031*
C21	0.85362 (10)	0.7177 (2)	0.45081 (4)	0.0177 (3)
C22	0.78158 (10)	0.8268 (2)	0.40773 (4)	0.0206 (3)
H22B	0.7264	0.9290	0.4169	0.025*
H22A	0.7431	0.7111	0.3859	0.025*
C23	0.81782 (12)	1.1718 (2)	0.35705 (5)	0.0270 (3)
H23C	0.7581	1.1263	0.3314	0.032*
H23B	0.8756	1.2467	0.3442	0.032*
H23A	0.7893	1.2760	0.3779	0.032*
C24	0.83161 (10)	0.5412 (2)	0.47796 (4)	0.0190 (3)
H24A	0.8872	0.4903	0.5031	0.023*
C25	0.72309 (11)	0.4285 (2)	0.46889 (4)	0.0201 (3)
C28	0.61577 (12)	0.1322 (3)	0.49483 (5)	0.0279 (3)
H28C	0.6234	0.0062	0.5170	0.033*
H28B	0.5913	0.0751	0.4628	0.033*
H28A	0.5615	0.2395	0.5021	0.033*
O1	0.33343 (8)	0.18484 (15)	0.39400 (3)	0.0210 (2)
O6	0.23724 (7)	0.54910 (15)	0.31945 (3)	0.0197 (2)
O12	0.04472 (8)	−0.02687 (16)	0.25726 (3)	0.0231 (2)
O13	−0.09856 (7)	0.22621 (17)	0.24354 (3)	0.0248 (2)
O15	0.91270 (7)	0.81006 (17)	0.35392 (3)	0.0232 (2)
O20	0.95504 (7)	0.82156 (16)	0.46110 (3)	0.0205 (2)
O26	0.64051 (8)	0.48260 (19)	0.43955 (4)	0.0318 (3)
O27	0.72256 (7)	0.24603 (16)	0.49859 (3)	0.0239 (2)

	U11	U22	U33	U12	U13	U23
C2	0.0185 (6)	0.0160 (6)	0.0180 (6)	−0.0016 (5)	0.0051 (5)	−0.0007 (5)
C3	0.0155 (6)	0.0168 (6)	0.0198 (6)	−0.0014 (5)	0.0032 (4)	0.0003 (5)
C4	0.0191 (6)	0.0178 (6)	0.0204 (6)	0.0004 (5)	0.0012 (5)	−0.0026 (5)
C5	0.0257 (6)	0.0192 (6)	0.0193 (6)	0.0023 (5)	0.0059 (5)	−0.0015 (5)
C7	0.0227 (6)	0.0163 (6)	0.0147 (5)	−0.0028 (5)	0.0050 (5)	−0.0003 (5)
C8	0.0192 (6)	0.0168 (6)	0.0217 (6)	−0.0007 (5)	0.0041 (5)	−0.0019 (5)
C9	0.0190 (6)	0.0199 (6)	0.0246 (6)	0.0001 (5)	0.0044 (5)	−0.0008 (5)
C10	0.0214 (6)	0.0181 (6)	0.0189 (6)	0.0016 (5)	0.0024 (5)	−0.0004 (5)
C11	0.0195 (6)	0.0226 (6)	0.0150 (5)	−0.0006 (5)	0.0041 (5)	0.0002 (5)
C14	0.0212 (7)	0.0321 (8)	0.0356 (8)	−0.0056 (6)	−0.0011 (6)	−0.0088 (6)
C16	0.0199 (6)	0.0196 (6)	0.0176 (6)	0.0025 (5)	0.0041 (5)	−0.0012 (5)
C17	0.0246 (6)	0.0179 (6)	0.0168 (6)	−0.0026 (5)	0.0022 (5)	0.0013 (5)
C18	0.0198 (6)	0.0295 (7)	0.0242 (6)	−0.0041 (5)	0.0029 (5)	0.0051 (6)
C19	0.0200 (6)	0.0307 (7)	0.0265 (7)	0.0047 (5)	0.0062 (5)	0.0011 (6)
C21	0.0163 (6)	0.0210 (6)	0.0160 (6)	0.0008 (5)	0.0032 (4)	−0.0031 (5)
C22	0.0178 (6)	0.0242 (6)	0.0195 (6)	0.0029 (5)	0.0029 (5)	0.0025 (5)
C23	0.0314 (7)	0.0261 (7)	0.0234 (6)	0.0069 (6)	0.0052 (5)	0.0065 (6)
C24	0.0166 (6)	0.0231 (6)	0.0165 (6)	0.0007 (5)	0.0012 (4)	0.0012 (5)
C25	0.0206 (6)	0.0233 (6)	0.0171 (6)	−0.0001 (5)	0.0055 (5)	−0.0002 (5)
C28	0.0256 (7)	0.0306 (7)	0.0281 (7)	−0.0105 (6)	0.0070 (5)	0.0010 (6)
O1	0.0282 (5)	0.0169 (4)	0.0198 (4)	−0.0007 (4)	0.0090 (4)	0.0002 (3)
O6	0.0196 (4)	0.0157 (4)	0.0214 (4)	−0.0003 (3)	−0.0013 (3)	−0.0007 (3)
O12	0.0236 (5)	0.0209 (5)	0.0239 (5)	−0.0012 (4)	0.0029 (4)	−0.0036 (4)
O13	0.0181 (4)	0.0262 (5)	0.0274 (5)	−0.0016 (4)	−0.0014 (4)	−0.0060 (4)
O15	0.0203 (5)	0.0283 (5)	0.0209 (4)	0.0026 (4)	0.0038 (4)	−0.0062 (4)
O20	0.0195 (4)	0.0232 (5)	0.0175 (4)	−0.0042 (4)	0.0003 (3)	0.0037 (4)
O26	0.0184 (5)	0.0438 (6)	0.0305 (5)	−0.0051 (4)	−0.0022 (4)	0.0121 (5)
O27	0.0211 (5)	0.0237 (5)	0.0264 (5)	−0.0046 (4)	0.0033 (4)	0.0048 (4)

C2—O1	1.4529 (14)	C16—O15	1.4424 (15)
C2—C9	1.5164 (17)	C16—C23	1.5157 (18)
C2—C8	1.5283 (17)	C16—C17	1.5274 (17)
C2—C3	1.5333 (17)	C16—C22	1.5297 (17)
C3—O6	1.4555 (14)	C17—O20	1.4610 (15)
C3—C4	1.5131 (17)	C17—C18	1.5082 (18)
C3—H3A	0.9800	C17—H17A	0.9800
C4—C5	1.5203 (18)	C18—C19	1.517 (2)
C4—H4B	0.9700	C18—H18B	0.9700
C4—H4A	0.9700	C18—H18A	0.9700
C5—O1	1.4359 (15)	C19—O15	1.4369 (15)
C5—H5B	0.9700	C19—H19B	0.9700
C5—H5A	0.9700	C19—H19A	0.9700
C7—C10	1.3428 (18)	C21—C24	1.3433 (18)
C7—O6	1.3581 (15)	C21—O20	1.3516 (15)
C7—C8	1.4967 (17)	C21—C22	1.4994 (17)
C8—H8B	0.9700	C22—H22B	0.9700
C8—H8A	0.9700	C22—H22A	0.9700
C9—H9C	0.9600	C23—H23C	0.9600
C9—H9B	0.9600	C23—H23B	0.9600
C9—H9A	0.9600	C23—H23A	0.9600
C10—C11	1.4537 (17)	C24—C25	1.4494 (17)
C10—H10A	0.9300	C24—H24A	0.9300
C11—O12	1.2139 (16)	C25—O26	1.2131 (16)
C11—O13	1.3565 (15)	C25—O27	1.3576 (16)
C14—O13	1.4403 (16)	C28—O27	1.4420 (15)
C14—H14C	0.9600	C28—H28C	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
O1—C2—C9	108.71 (10)	O15—C16—C22	109.33 (10)
O1—C2—C8	109.72 (10)	C23—C16—C22	114.41 (11)
C9—C2—C8	115.22 (10)	C17—C16—C22	103.44 (10)
O1—C2—C3	104.73 (10)	O20—C17—C18	108.89 (10)
C9—C2—C3	114.60 (10)	O20—C17—C16	104.54 (10)
C8—C2—C3	103.27 (10)	C18—C17—C16	104.34 (10)
O6—C3—C4	108.98 (10)	O20—C17—H17A	112.8
O6—C3—C2	105.46 (9)	C18—C17—H17A	112.8
C4—C3—C2	105.03 (10)	C16—C17—H17A	112.8
O6—C3—H3A	112.3	C17—C18—C19	101.64 (10)
C4—C3—H3A	112.3	C17—C18—H18B	111.4
C2—C3—H3A	112.3	C19—C18—H18B	111.4
C3—C4—C5	101.48 (10)	C17—C18—H18A	111.4
C3—C4—H4B	111.5	C19—C18—H18A	111.4
C5—C4—H4B	111.5	H18B—C18—H18A	109.3
C3—C4—H4A	111.5	O15—C19—C18	105.78 (11)
C5—C4—H4A	111.5	O15—C19—H19B	110.6
H4B—C4—H4A	109.3	C18—C19—H19B	110.6
O1—C5—C4	106.05 (10)	O15—C19—H19A	110.6
O1—C5—H5B	110.5	C18—C19—H19A	110.6
C4—C5—H5B	110.5	H19B—C19—H19A	108.7
O1—C5—H5A	110.5	C24—C21—O20	119.59 (11)
C4—C5—H5A	110.5	C24—C21—C22	130.07 (11)
H5B—C5—H5A	108.7	O20—C21—C22	110.34 (11)
C10—C7—O6	118.61 (11)	C21—C22—C16	103.27 (10)
C10—C7—C8	131.31 (12)	C21—C22—H22B	111.1
O6—C7—C8	110.06 (10)	C16—C22—H22B	111.1
C7—C8—C2	103.59 (10)	C21—C22—H22A	111.1
C7—C8—H8B	111.0	C16—C22—H22A	111.1
C2—C8—H8B	111.0	H22B—C22—H22A	109.1
C7—C8—H8A	111.0	C16—C23—H23C	109.5
C2—C8—H8A	111.0	C16—C23—H23B	109.5
H8B—C8—H8A	109.0	H23C—C23—H23B	109.5
C2—C9—H9C	109.5	C16—C23—H23A	109.5
C2—C9—H9B	109.5	H23C—C23—H23A	109.5
H9C—C9—H9B	109.5	H23B—C23—H23A	109.5
C2—C9—H9A	109.5	C21—C24—C25	121.40 (11)
H9C—C9—H9A	109.5	C21—C24—H24A	119.3
H9B—C9—H9A	109.5	C25—C24—H24A	119.3
C7—C10—C11	122.15 (12)	O26—C25—O27	121.75 (12)
C7—C10—H10A	118.9	O26—C25—C24	127.21 (12)
C11—C10—H10A	118.9	O27—C25—C24	111.04 (11)
O12—C11—O13	122.40 (12)	O27—C28—H28C	109.5
O12—C11—C10	127.40 (12)	O27—C28—H28B	109.5
O13—C11—C10	110.20 (11)	H28C—C28—H28B	109.5
O13—C14—H14C	109.5	O27—C28—H28A	109.5
O13—C14—H14B	109.5	H28C—C28—H28A	109.5
H14C—C14—H14B	109.5	H28B—C28—H28A	109.5
O13—C14—H14A	109.5	C5—O1—C2	110.45 (9)
H14C—C14—H14A	109.5	C7—O6—C3	111.12 (9)
H14B—C14—H14A	109.5	C11—O13—C14	114.63 (11)
O15—C16—C23	108.93 (10)	C19—O15—C16	110.61 (9)
O15—C16—C17	104.78 (10)	C21—O20—C17	111.13 (9)
C23—C16—C17	115.38 (11)	C25—O27—C28	115.34 (10)
O1—C2—C3—O6	−92.66 (10)	O20—C21—C22—C16	16.47 (13)
C9—C2—C3—O6	148.3 (1)	O15—C16—C22—C21	85.89 (11)
C8—C2—C3—O6	22.21 (12)	C23—C16—C22—C21	−151.64 (11)
O1—C2—C3—C4	22.4 (1)	C17—C16—C22—C21	−25.31 (12)
C9—C2—C3—C4	−96.62 (12)	O20—C21—C24—C25	178.52 (11)
C8—C2—C3—C4	137.27 (10)	C22—C21—C24—C25	−2.3 (2)
O6—C3—C4—C5	79.11 (11)	C21—C24—C25—O26	−4.7 (2)
C2—C3—C4—C5	−33.49 (12)	C21—C24—C25—O27	175.91 (11)
C3—C4—C5—O1	33.07 (12)	C4—C5—O1—C2	−20.25 (13)
C10—C7—C8—C2	−161.49 (13)	C9—C2—O1—C5	121.59 (11)
O6—C7—C8—C2	19.87 (13)	C8—C2—O1—C5	−111.59 (11)
O1—C2—C8—C7	86.28 (11)	C3—C2—O1—C5	−1.33 (13)
C9—C2—C8—C7	−150.66 (10)	C10—C7—O6—C3	175.36 (11)
C3—C2—C8—C7	−24.94 (12)	C8—C7—O6—C3	−5.81 (13)
O6—C7—C10—C11	179.36 (11)	C4—C3—O6—C7	−123.13 (11)
C8—C7—C10—C11	0.8 (2)	C2—C3—O6—C7	−10.82 (13)
C7—C10—C11—O12	−2.6 (2)	O12—C11—O13—C14	0.98 (17)
C7—C10—C11—O13	177.98 (11)	C10—C11—O13—C14	−179.57 (11)
O15—C16—C17—O20	−88.79 (11)	C18—C19—O15—C16	−17.45 (14)
C23—C16—C17—O20	151.4 (1)	C23—C16—O15—C19	119.00 (12)
C22—C16—C17—O20	25.73 (12)	C17—C16—O15—C19	−4.99 (13)
O15—C16—C17—C18	25.5 (1)	C22—C16—O15—C19	−115.31 (11)
C23—C16—C17—C18	−94.26 (13)	C24—C21—O20—C17	179.38 (11)
C22—C16—C17—C18	140.03 (11)	C22—C21—O20—C17	0.07 (14)
O20—C17—C18—C19	76.14 (12)	C18—C17—O20—C21	−127.75 (11)
C16—C17—C18—C19	−35.04 (13)	C16—C17—O20—C21	−16.70 (13)
C17—C18—C19—O15	32.43 (13)	O26—C25—O27—C28	−3.84 (18)
C24—C21—C22—C16	−162.75 (13)	C24—C25—O27—C28	175.63 (11)