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The molecular structure of the title compound, C14H22O6, has four chiral centres, for which only the relative configuration has been unequivocally determined. The molecules form a supramolecular array of infinite one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005762/bt6248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005762/bt6248Isup2.hkl
Contains datablock I

CCDC reference: 209964

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.075
  • Data-to-parameter ratio = 9.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 1717 Count of symmetry unique reflns 1720 Completeness (_total/calc) 99.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title structure, (I) (Fig. 1), was synthesized as part of a study on the KMnO4-mediated oxidative cyclization of 1,5,9-trienes (Brown et al., 2002). The structure is composed of two substituted furan moieties connected to each other at the 2- and 5-positions, and exhibits bond lengths and angles consistent with expected values (Orpen et al., 1992) derived from structures in the Cambridge Stuructural Database (Allen, 2002).

The molecular structure of (I) contains two furan rings which, from puckering analysis (Cremer & Pople, 1975), adopt an envelope (about C3) and twisted (about C7—C8) conformations. The molecule contains four chiral centres which, for the given absolute configuration, are C4 = R, C6 = R, C9 = S and C11 = S.

The crystal structure is a one-dimensional chain arising from a hydrogen-bonded O4—H4···O1i interaction [symmetry code: (i) −x, −y, z + 0.5], with a donor–acceptor separation of 2.8931 (16) Å.

Experimental top

Ethyl (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienoate was oxidized with KMnO4 followed by Pb(OAc)4 to afford the title compound, (I), as a colourless oil which solidified on standing (Brown et al., 2002). Recrystallization from ethyl acetate/hexane gave colourless plates suitable for X-ray structure determination.

Refinement top

Compound (I) crystallized in the chiral space group Pna21; however, due to the small anomalous differences of the substituent elements, the Flack (1983) parameter refined to a meaningless value and hence only the relative stereochemistry has been determined. H atoms are included in constrained positions, with torsion angles allowed to freely refine in the case of methyl and alcohol moieties.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002).

Figures top
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids), with specific H atoms retained to show relative configuration.
(I) top
Crystal data top
C14H22O6Dx = 1.343 Mg m3
Mr = 286.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 15124 reflections
a = 9.3133 (3) Åθ = 2.9–27.5°
b = 15.4441 (4) ŵ = 0.10 mm1
c = 9.8424 (3) ÅT = 120 K
V = 1415.69 (7) Å3Plate, colourless
Z = 40.26 × 0.22 × 0.1 mm
F(000) = 616
Data collection top
Bruker-Nonius KappaCCD
diffractometer
1717 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1555 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
ϕ andω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1012
Tmin = 0.973, Tmax = 0.990k = 1920
14735 measured reflectionsl = 1212
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0417P)2 + 0.1548P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.030(Δ/σ)max = 0.005
wR(F2) = 0.075Δρmax = 0.17 e Å3
S = 1.08Δρmin = 0.17 e Å3
1717 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
186 parametersExtinction coefficient: 0.009 (2)
1 restraint
Crystal data top
C14H22O6V = 1415.69 (7) Å3
Mr = 286.32Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 9.3133 (3) ŵ = 0.10 mm1
b = 15.4441 (4) ÅT = 120 K
c = 9.8424 (3) Å0.26 × 0.22 × 0.1 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
1717 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
1555 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.990Rint = 0.061
14735 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.075H-atom parameters constrained
S = 1.08Δρmax = 0.17 e Å3
1717 reflectionsΔρmin = 0.17 e Å3
186 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.37380 (15)0.06606 (9)0.24155 (16)0.0188 (3)
C20.50287 (17)0.09643 (10)0.31964 (17)0.0229 (3)
H2A0.58790.10110.25970.027*
H2B0.48470.15340.36230.027*
C30.52451 (16)0.02669 (9)0.42679 (16)0.0208 (3)
H3A0.62770.0180.44650.025*
H3B0.47390.04160.51210.025*
C40.45854 (16)0.05412 (9)0.35985 (15)0.0182 (3)
C50.56890 (17)0.10534 (10)0.27875 (17)0.0236 (3)
H5A0.62190.0660.21890.035*
H5B0.6360.13370.34120.035*
H5C0.51980.14930.2240.035*
C60.37830 (15)0.11338 (9)0.45706 (16)0.0174 (3)
H60.45040.14360.51560.021*
C70.28343 (15)0.18203 (10)0.38981 (16)0.0208 (3)
H7A0.3370.23660.37470.025*
H7B0.24460.16120.30210.025*
C80.16444 (17)0.19414 (9)0.49444 (17)0.0224 (3)
H8A0.07530.21550.45120.027*
H8B0.1940.23520.56640.027*
C90.14376 (16)0.10315 (9)0.55174 (16)0.0188 (3)
C100.09630 (18)0.10143 (11)0.69963 (17)0.0266 (4)
H10A0.10540.04240.73520.04*
H10B0.0040.12010.7060.04*
H10C0.1570.14060.75290.04*
C110.03997 (16)0.05050 (9)0.46021 (15)0.0192 (3)
H110.08460.04480.36820.023*
C120.01326 (16)0.03991 (10)0.51586 (16)0.0209 (3)
C130.10388 (18)0.18003 (9)0.5515 (2)0.0309 (4)
H13A0.01280.20520.51790.037*
H13B0.10030.17790.6520.037*
C140.22797 (18)0.23337 (10)0.50574 (19)0.0321 (4)
H14A0.23270.23290.40630.048*
H14B0.21590.2930.53780.048*
H14C0.3170.20930.54310.048*
O10.29969 (11)0.10705 (7)0.16442 (12)0.0260 (3)
O20.35204 (11)0.01858 (6)0.26424 (11)0.0196 (2)
O30.28451 (10)0.06383 (6)0.54379 (11)0.0188 (2)
O40.09369 (11)0.09359 (7)0.44542 (13)0.0249 (3)
H40.1460.08260.51280.037*
O50.09641 (13)0.06047 (7)0.57232 (14)0.0331 (3)
O60.12410 (11)0.09335 (6)0.49619 (12)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0168 (7)0.0206 (7)0.0190 (8)0.0010 (5)0.0031 (6)0.0007 (6)
C20.0196 (8)0.0243 (7)0.0246 (8)0.0029 (6)0.0001 (6)0.0006 (6)
C30.0185 (7)0.0244 (7)0.0195 (8)0.0038 (6)0.0014 (6)0.0008 (6)
C40.0154 (7)0.0221 (7)0.0172 (7)0.0009 (5)0.0027 (6)0.0011 (6)
C50.0212 (8)0.0274 (8)0.0224 (8)0.0022 (6)0.0022 (6)0.0012 (7)
C60.0145 (7)0.0199 (7)0.0176 (7)0.0032 (5)0.0001 (6)0.0009 (6)
C70.0183 (7)0.0188 (7)0.0254 (7)0.0016 (6)0.0005 (6)0.0031 (6)
C80.0201 (7)0.0169 (6)0.0302 (8)0.0003 (6)0.0005 (6)0.0015 (7)
C90.0151 (7)0.0196 (6)0.0218 (8)0.0019 (5)0.0006 (6)0.0006 (6)
C100.0191 (8)0.0355 (9)0.0250 (9)0.0017 (6)0.0024 (6)0.0068 (7)
C110.0154 (7)0.0204 (7)0.0216 (8)0.0008 (6)0.0009 (6)0.0001 (6)
C120.0177 (7)0.0212 (7)0.0236 (8)0.0010 (5)0.0013 (6)0.0022 (6)
C130.0264 (8)0.0185 (7)0.0479 (11)0.0009 (6)0.0046 (8)0.0064 (8)
C140.0264 (8)0.0224 (7)0.0476 (11)0.0025 (6)0.0009 (8)0.0007 (8)
O10.0218 (6)0.0250 (5)0.0312 (6)0.0004 (4)0.0049 (5)0.0074 (5)
O20.0193 (5)0.0195 (5)0.0198 (5)0.0002 (4)0.0048 (4)0.0021 (4)
O30.0139 (5)0.0208 (5)0.0216 (5)0.0006 (4)0.0018 (4)0.0034 (4)
O40.0169 (5)0.0276 (5)0.0301 (6)0.0034 (4)0.0019 (5)0.0042 (5)
O50.0226 (6)0.0236 (5)0.0531 (8)0.0018 (5)0.0127 (6)0.0023 (6)
O60.0188 (5)0.0179 (5)0.0335 (6)0.0000 (4)0.0036 (5)0.0014 (5)
Geometric parameters (Å, º) top
C1—O11.2056 (19)C8—H8A0.99
C1—O21.3416 (17)C8—H8B0.99
C1—C21.502 (2)C9—O31.4468 (17)
C2—C31.521 (2)C9—C101.521 (2)
C2—H2A0.99C9—C111.551 (2)
C2—H2B0.99C10—H10A0.98
C3—C41.539 (2)C10—H10B0.98
C3—H3A0.99C10—H10C0.98
C3—H3B0.99C11—O41.4190 (17)
C4—O21.4733 (17)C11—C121.520 (2)
C4—C61.520 (2)C11—H111
C4—C51.523 (2)C12—O51.2053 (19)
C5—H5A0.98C12—O61.3358 (18)
C5—H5B0.98C13—O61.4573 (17)
C5—H5C0.98C13—C141.489 (2)
C6—O31.4412 (17)C13—H13A0.99
C6—C71.531 (2)C13—H13B0.99
C6—H61C14—H14A0.98
C7—C81.524 (2)C14—H14B0.98
C7—H7A0.99C14—H14C0.98
C7—H7B0.99O4—H40.84
C8—C91.526 (2)
O1—C1—O2122.00 (14)C9—C8—H8A111.1
O1—C1—C2128.06 (14)C7—C8—H8B111.1
O2—C1—C2109.88 (13)C9—C8—H8B111.1
C1—C2—C3103.87 (12)H8A—C8—H8B109.1
C1—C2—H2A111O3—C9—C10107.92 (12)
C3—C2—H2A111O3—C9—C8104.60 (11)
C1—C2—H2B111C10—C9—C8113.97 (13)
C3—C2—H2B111O3—C9—C11108.25 (11)
H2A—C2—H2B109C10—C9—C11111.43 (12)
C2—C3—C4102.98 (12)C8—C9—C11110.28 (13)
C2—C3—H3A111.2C9—C10—H10A109.5
C4—C3—H3A111.2C9—C10—H10B109.5
C2—C3—H3B111.2H10A—C10—H10B109.5
C4—C3—H3B111.2C9—C10—H10C109.5
H3A—C3—H3B109.1H10A—C10—H10C109.5
O2—C4—C6107.18 (11)H10B—C10—H10C109.5
O2—C4—C5108.24 (12)O4—C11—C12108.91 (12)
C6—C4—C5110.42 (12)O4—C11—C9111.12 (11)
O2—C4—C3103.89 (11)C12—C11—C9111.97 (12)
C6—C4—C3114.52 (12)O4—C11—H11108.2
C5—C4—C3112.09 (12)C12—C11—H11108.2
C4—C5—H5A109.5C9—C11—H11108.2
C4—C5—H5B109.5O5—C12—O6123.98 (14)
H5A—C5—H5B109.5O5—C12—C11123.14 (13)
C4—C5—H5C109.5O6—C12—C11112.88 (12)
H5A—C5—H5C109.5O6—C13—C14107.15 (13)
H5B—C5—H5C109.5O6—C13—H13A110.3
O3—C6—C4110.55 (11)C14—C13—H13A110.3
O3—C6—C7105.91 (11)O6—C13—H13B110.3
C4—C6—C7115.37 (13)C14—C13—H13B110.3
O3—C6—H6108.3H13A—C13—H13B108.5
C4—C6—H6108.3C13—C14—H14A109.5
C7—C6—H6108.3C13—C14—H14B109.5
C8—C7—C6102.26 (12)H14A—C14—H14B109.5
C8—C7—H7A111.3C13—C14—H14C109.5
C6—C7—H7A111.3H14A—C14—H14C109.5
C8—C7—H7B111.3H14B—C14—H14C109.5
C6—C7—H7B111.3C1—O2—C4111.57 (11)
H7A—C7—H7B109.2C6—O3—C9110.99 (10)
C7—C8—C9103.20 (12)C11—O4—H4109.5
C7—C8—H8A111.1C12—O6—C13114.43 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.842.102.8931 (16)157
Symmetry code: (i) x, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H22O6
Mr286.32
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)120
a, b, c (Å)9.3133 (3), 15.4441 (4), 9.8424 (3)
V3)1415.69 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.26 × 0.22 × 0.1
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.973, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
14735, 1717, 1555
Rint0.061
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.075, 1.08
No. of reflections1717
No. of parameters186
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.17

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.842.102.8931 (16)157
Symmetry code: (i) x, y, z+1/2.
 

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