Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005762/bt6248sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005762/bt6248Isup2.hkl |
CCDC reference: 209964
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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.
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.
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.
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).
Fig. 1. View of (I) (50% probability displacement ellipsoids), with specific H atoms retained to show relative configuration. |
C14H22O6 | Dx = 1.343 Mg m−3 |
Mr = 286.32 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 15124 reflections |
a = 9.3133 (3) Å | θ = 2.9–27.5° |
b = 15.4441 (4) Å | µ = 0.10 mm−1 |
c = 9.8424 (3) Å | T = 120 K |
V = 1415.69 (7) Å3 | Plate, colourless |
Z = 4 | 0.26 × 0.22 × 0.1 mm |
F(000) = 616 |
Bruker-Nonius KappaCCD diffractometer | 1717 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1555 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ϕ andω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −10→12 |
Tmin = 0.973, Tmax = 0.990 | k = −19→20 |
14735 measured reflections | l = −12→12 |
Refinement on F2 | H-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) = 0.075 | Δρmax = 0.17 e Å−3 |
S = 1.08 | Δρmin = −0.17 e Å−3 |
1717 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
186 parameters | Extinction coefficient: 0.009 (2) |
1 restraint |
C14H22O6 | V = 1415.69 (7) Å3 |
Mr = 286.32 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 9.3133 (3) Å | µ = 0.10 mm−1 |
b = 15.4441 (4) Å | T = 120 K |
c = 9.8424 (3) Å | 0.26 × 0.22 × 0.1 mm |
Bruker-Nonius KappaCCD diffractometer | 1717 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 1555 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.990 | Rint = 0.061 |
14735 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 1 restraint |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.17 e Å−3 |
1717 reflections | Δρmin = −0.17 e Å−3 |
186 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.37380 (15) | −0.06606 (9) | 0.24155 (16) | 0.0188 (3) | |
C2 | 0.50287 (17) | −0.09643 (10) | 0.31964 (17) | 0.0229 (3) | |
H2A | 0.5879 | −0.1011 | 0.2597 | 0.027* | |
H2B | 0.4847 | −0.1534 | 0.3623 | 0.027* | |
C3 | 0.52451 (16) | −0.02669 (9) | 0.42679 (16) | 0.0208 (3) | |
H3A | 0.6277 | −0.018 | 0.4465 | 0.025* | |
H3B | 0.4739 | −0.0416 | 0.5121 | 0.025* | |
C4 | 0.45854 (16) | 0.05412 (9) | 0.35985 (15) | 0.0182 (3) | |
C5 | 0.56890 (17) | 0.10534 (10) | 0.27875 (17) | 0.0236 (3) | |
H5A | 0.6219 | 0.066 | 0.2189 | 0.035* | |
H5B | 0.636 | 0.1337 | 0.3412 | 0.035* | |
H5C | 0.5198 | 0.1493 | 0.224 | 0.035* | |
C6 | 0.37830 (15) | 0.11338 (9) | 0.45706 (16) | 0.0174 (3) | |
H6 | 0.4504 | 0.1436 | 0.5156 | 0.021* | |
C7 | 0.28343 (15) | 0.18203 (10) | 0.38981 (16) | 0.0208 (3) | |
H7A | 0.337 | 0.2366 | 0.3747 | 0.025* | |
H7B | 0.2446 | 0.1612 | 0.3021 | 0.025* | |
C8 | 0.16444 (17) | 0.19414 (9) | 0.49444 (17) | 0.0224 (3) | |
H8A | 0.0753 | 0.2155 | 0.4512 | 0.027* | |
H8B | 0.194 | 0.2352 | 0.5664 | 0.027* | |
C9 | 0.14376 (16) | 0.10315 (9) | 0.55174 (16) | 0.0188 (3) | |
C10 | 0.09630 (18) | 0.10143 (11) | 0.69963 (17) | 0.0266 (4) | |
H10A | 0.1054 | 0.0424 | 0.7352 | 0.04* | |
H10B | −0.004 | 0.1201 | 0.706 | 0.04* | |
H10C | 0.157 | 0.1406 | 0.7529 | 0.04* | |
C11 | 0.03997 (16) | 0.05050 (9) | 0.46021 (15) | 0.0192 (3) | |
H11 | 0.0846 | 0.0448 | 0.3682 | 0.023* | |
C12 | 0.01326 (16) | −0.03991 (10) | 0.51586 (16) | 0.0209 (3) | |
C13 | 0.10388 (18) | −0.18003 (9) | 0.5515 (2) | 0.0309 (4) | |
H13A | 0.0128 | −0.2052 | 0.5179 | 0.037* | |
H13B | 0.1003 | −0.1779 | 0.652 | 0.037* | |
C14 | 0.22797 (18) | −0.23337 (10) | 0.50574 (19) | 0.0321 (4) | |
H14A | 0.2327 | −0.2329 | 0.4063 | 0.048* | |
H14B | 0.2159 | −0.293 | 0.5378 | 0.048* | |
H14C | 0.317 | −0.2093 | 0.5431 | 0.048* | |
O1 | 0.29969 (11) | −0.10705 (7) | 0.16442 (12) | 0.0260 (3) | |
O2 | 0.35204 (11) | 0.01858 (6) | 0.26424 (11) | 0.0196 (2) | |
O3 | 0.28451 (10) | 0.06383 (6) | 0.54379 (11) | 0.0188 (2) | |
O4 | −0.09369 (11) | 0.09359 (7) | 0.44542 (13) | 0.0249 (3) | |
H4 | −0.146 | 0.0826 | 0.5128 | 0.037* | |
O5 | −0.09641 (13) | −0.06047 (7) | 0.57232 (14) | 0.0331 (3) | |
O6 | 0.12410 (11) | −0.09335 (6) | 0.49619 (12) | 0.0234 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0168 (7) | 0.0206 (7) | 0.0190 (8) | 0.0010 (5) | 0.0031 (6) | 0.0007 (6) |
C2 | 0.0196 (8) | 0.0243 (7) | 0.0246 (8) | 0.0029 (6) | 0.0001 (6) | −0.0006 (6) |
C3 | 0.0185 (7) | 0.0244 (7) | 0.0195 (8) | 0.0038 (6) | −0.0014 (6) | −0.0008 (6) |
C4 | 0.0154 (7) | 0.0221 (7) | 0.0172 (7) | −0.0009 (5) | −0.0027 (6) | −0.0011 (6) |
C5 | 0.0212 (8) | 0.0274 (8) | 0.0224 (8) | −0.0022 (6) | 0.0022 (6) | −0.0012 (7) |
C6 | 0.0145 (7) | 0.0199 (7) | 0.0176 (7) | −0.0032 (5) | 0.0001 (6) | −0.0009 (6) |
C7 | 0.0183 (7) | 0.0188 (7) | 0.0254 (7) | −0.0016 (6) | 0.0005 (6) | 0.0031 (6) |
C8 | 0.0201 (7) | 0.0169 (6) | 0.0302 (8) | 0.0003 (6) | 0.0005 (6) | −0.0015 (7) |
C9 | 0.0151 (7) | 0.0196 (6) | 0.0218 (8) | 0.0019 (5) | 0.0006 (6) | −0.0006 (6) |
C10 | 0.0191 (8) | 0.0355 (9) | 0.0250 (9) | −0.0017 (6) | 0.0024 (6) | −0.0068 (7) |
C11 | 0.0154 (7) | 0.0204 (7) | 0.0216 (8) | 0.0008 (6) | −0.0009 (6) | −0.0001 (6) |
C12 | 0.0177 (7) | 0.0212 (7) | 0.0236 (8) | −0.0010 (5) | −0.0013 (6) | −0.0022 (6) |
C13 | 0.0264 (8) | 0.0185 (7) | 0.0479 (11) | −0.0009 (6) | 0.0046 (8) | 0.0064 (8) |
C14 | 0.0264 (8) | 0.0224 (7) | 0.0476 (11) | 0.0025 (6) | −0.0009 (8) | −0.0007 (8) |
O1 | 0.0218 (6) | 0.0250 (5) | 0.0312 (6) | −0.0004 (4) | −0.0049 (5) | −0.0074 (5) |
O2 | 0.0193 (5) | 0.0195 (5) | 0.0198 (5) | −0.0002 (4) | −0.0048 (4) | −0.0021 (4) |
O3 | 0.0139 (5) | 0.0208 (5) | 0.0216 (5) | −0.0006 (4) | 0.0018 (4) | 0.0034 (4) |
O4 | 0.0169 (5) | 0.0276 (5) | 0.0301 (6) | 0.0034 (4) | −0.0019 (5) | 0.0042 (5) |
O5 | 0.0226 (6) | 0.0236 (5) | 0.0531 (8) | −0.0018 (5) | 0.0127 (6) | 0.0023 (6) |
O6 | 0.0188 (5) | 0.0179 (5) | 0.0335 (6) | 0.0000 (4) | 0.0036 (5) | 0.0014 (5) |
C1—O1 | 1.2056 (19) | C8—H8A | 0.99 |
C1—O2 | 1.3416 (17) | C8—H8B | 0.99 |
C1—C2 | 1.502 (2) | C9—O3 | 1.4468 (17) |
C2—C3 | 1.521 (2) | C9—C10 | 1.521 (2) |
C2—H2A | 0.99 | C9—C11 | 1.551 (2) |
C2—H2B | 0.99 | C10—H10A | 0.98 |
C3—C4 | 1.539 (2) | C10—H10B | 0.98 |
C3—H3A | 0.99 | C10—H10C | 0.98 |
C3—H3B | 0.99 | C11—O4 | 1.4190 (17) |
C4—O2 | 1.4733 (17) | C11—C12 | 1.520 (2) |
C4—C6 | 1.520 (2) | C11—H11 | 1 |
C4—C5 | 1.523 (2) | C12—O5 | 1.2053 (19) |
C5—H5A | 0.98 | C12—O6 | 1.3358 (18) |
C5—H5B | 0.98 | C13—O6 | 1.4573 (17) |
C5—H5C | 0.98 | C13—C14 | 1.489 (2) |
C6—O3 | 1.4412 (17) | C13—H13A | 0.99 |
C6—C7 | 1.531 (2) | C13—H13B | 0.99 |
C6—H6 | 1 | C14—H14A | 0.98 |
C7—C8 | 1.524 (2) | C14—H14B | 0.98 |
C7—H7A | 0.99 | C14—H14C | 0.98 |
C7—H7B | 0.99 | O4—H4 | 0.84 |
C8—C9 | 1.526 (2) | ||
O1—C1—O2 | 122.00 (14) | C9—C8—H8A | 111.1 |
O1—C1—C2 | 128.06 (14) | C7—C8—H8B | 111.1 |
O2—C1—C2 | 109.88 (13) | C9—C8—H8B | 111.1 |
C1—C2—C3 | 103.87 (12) | H8A—C8—H8B | 109.1 |
C1—C2—H2A | 111 | O3—C9—C10 | 107.92 (12) |
C3—C2—H2A | 111 | O3—C9—C8 | 104.60 (11) |
C1—C2—H2B | 111 | C10—C9—C8 | 113.97 (13) |
C3—C2—H2B | 111 | O3—C9—C11 | 108.25 (11) |
H2A—C2—H2B | 109 | C10—C9—C11 | 111.43 (12) |
C2—C3—C4 | 102.98 (12) | C8—C9—C11 | 110.28 (13) |
C2—C3—H3A | 111.2 | C9—C10—H10A | 109.5 |
C4—C3—H3A | 111.2 | C9—C10—H10B | 109.5 |
C2—C3—H3B | 111.2 | H10A—C10—H10B | 109.5 |
C4—C3—H3B | 111.2 | C9—C10—H10C | 109.5 |
H3A—C3—H3B | 109.1 | H10A—C10—H10C | 109.5 |
O2—C4—C6 | 107.18 (11) | H10B—C10—H10C | 109.5 |
O2—C4—C5 | 108.24 (12) | O4—C11—C12 | 108.91 (12) |
C6—C4—C5 | 110.42 (12) | O4—C11—C9 | 111.12 (11) |
O2—C4—C3 | 103.89 (11) | C12—C11—C9 | 111.97 (12) |
C6—C4—C3 | 114.52 (12) | O4—C11—H11 | 108.2 |
C5—C4—C3 | 112.09 (12) | C12—C11—H11 | 108.2 |
C4—C5—H5A | 109.5 | C9—C11—H11 | 108.2 |
C4—C5—H5B | 109.5 | O5—C12—O6 | 123.98 (14) |
H5A—C5—H5B | 109.5 | O5—C12—C11 | 123.14 (13) |
C4—C5—H5C | 109.5 | O6—C12—C11 | 112.88 (12) |
H5A—C5—H5C | 109.5 | O6—C13—C14 | 107.15 (13) |
H5B—C5—H5C | 109.5 | O6—C13—H13A | 110.3 |
O3—C6—C4 | 110.55 (11) | C14—C13—H13A | 110.3 |
O3—C6—C7 | 105.91 (11) | O6—C13—H13B | 110.3 |
C4—C6—C7 | 115.37 (13) | C14—C13—H13B | 110.3 |
O3—C6—H6 | 108.3 | H13A—C13—H13B | 108.5 |
C4—C6—H6 | 108.3 | C13—C14—H14A | 109.5 |
C7—C6—H6 | 108.3 | C13—C14—H14B | 109.5 |
C8—C7—C6 | 102.26 (12) | H14A—C14—H14B | 109.5 |
C8—C7—H7A | 111.3 | C13—C14—H14C | 109.5 |
C6—C7—H7A | 111.3 | H14A—C14—H14C | 109.5 |
C8—C7—H7B | 111.3 | H14B—C14—H14C | 109.5 |
C6—C7—H7B | 111.3 | C1—O2—C4 | 111.57 (11) |
H7A—C7—H7B | 109.2 | C6—O3—C9 | 110.99 (10) |
C7—C8—C9 | 103.20 (12) | C11—O4—H4 | 109.5 |
C7—C8—H8A | 111.1 | C12—O6—C13 | 114.43 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.84 | 2.10 | 2.8931 (16) | 157 |
Symmetry code: (i) −x, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H22O6 |
Mr | 286.32 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 120 |
a, b, c (Å) | 9.3133 (3), 15.4441 (4), 9.8424 (3) |
V (Å3) | 1415.69 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.22 × 0.1 |
Data collection | |
Diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.973, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14735, 1717, 1555 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.075, 1.08 |
No. of reflections | 1717 |
No. of parameters | 186 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.84 | 2.10 | 2.8931 (16) | 157 |
Symmetry code: (i) −x, −y, z+1/2. |
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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.