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The title compound, C12H16O4, has an unconventional weak hydrogen-bonding pattern. A network of weak inter­molecular hydrogen bonds between an alkane group and the carbonyl groups stabilizes the mol­ecular packing. The asymmetric unit contains one half-mol­ecule and the complete mol­ecule is generated by an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005745/ac6231sup1.cif
Contains datablocks global, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005745/ac62314sup2.hkl
Contains datablock 4

CCDC reference: 601093

Key indicators

  • Single-crystal X-ray study
  • T = 301 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.123
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.754 0.984 Tmin(prime) and Tmax expected: 0.952 0.984 RR(prime) = 0.792 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79 PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. O1 .. 2.67 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

(E,E)-1,8-Dioxacyclotetradeca-3,10-diene-2,9-dione top
Crystal data top
C12H16O4Z = 1
Mr = 224.25F(000) = 120
Triclinic, P1Dx = 1.272 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.442 (3) ÅCell parameters from 938 reflections
b = 6.665 (3) Åθ = 28.3–0.9°
c = 7.757 (4) ŵ = 0.10 mm1
α = 72.037 (7)°T = 301 K
β = 77.661 (8)°Column, colorless
γ = 68.409 (7)°0.51 × 0.41 × 0.17 mm
V = 292.7 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1440 independent reflections
Radiation source: fine-focus sealed tube1278 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 88
Tmin = 0.754, Tmax = 0.984k = 88
5226 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0712P)2 + 0.031P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1440 reflectionsΔρmax = 0.20 e Å3
82 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.17 (3)
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.

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 (Å2) top
xyzUiso*/Ueq
O20.33098 (13)0.81151 (13)0.11673 (10)0.0483 (3)
C10.59655 (19)0.72251 (16)0.07816 (15)0.0446 (3)
C20.55029 (19)0.77086 (17)0.11113 (15)0.0454 (3)
C30.7891 (2)0.71892 (17)0.11454 (15)0.0465 (3)
O10.68569 (16)0.7824 (2)0.24410 (12)0.0713 (3)
C40.8471 (2)0.69366 (19)0.29840 (16)0.0537 (3)
H4A0.96270.55080.33390.064*
H4B0.71540.69320.38660.064*
C50.2471 (2)0.8963 (2)0.29373 (16)0.0558 (3)
H5A0.18370.79370.31140.067*
H5B0.36980.90860.38930.067*
C60.9303 (2)0.8781 (2)0.30483 (17)0.0551 (3)
H6A0.99700.83290.41740.066*
H6B1.04770.89230.20470.066*
H99A0.473 (2)0.712 (2)0.167 (2)0.058 (4)*
H99B0.903 (2)0.736 (2)0.0155 (19)0.056 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0550 (5)0.0481 (4)0.0446 (4)0.0188 (3)0.0124 (3)0.0087 (3)
C10.0498 (6)0.0361 (5)0.0437 (5)0.0097 (4)0.0075 (5)0.0080 (4)
C20.0514 (6)0.0372 (5)0.0472 (6)0.0100 (4)0.0076 (5)0.0142 (4)
C30.0499 (6)0.0390 (5)0.0454 (6)0.0070 (4)0.0080 (5)0.0108 (4)
O10.0604 (6)0.1010 (8)0.0499 (5)0.0190 (5)0.0001 (4)0.0284 (5)
C40.0597 (7)0.0478 (6)0.0483 (6)0.0105 (5)0.0186 (5)0.0051 (5)
C50.0686 (8)0.0579 (7)0.0480 (6)0.0211 (6)0.0186 (5)0.0142 (5)
C60.0546 (7)0.0628 (7)0.0495 (6)0.0173 (5)0.0195 (5)0.0094 (5)
Geometric parameters (Å, º) top
O2—C21.3449 (15)C4—C61.5281 (19)
O2—C51.4528 (14)C4—H4A0.9700
C1—C31.3201 (18)C4—H4B0.9700
C1—C21.4742 (16)C5—C6i1.5069 (19)
C1—H99A0.942 (15)C5—H5A0.9700
C2—O11.2027 (15)C5—H5B0.9700
C3—C41.4952 (16)C6—H6A0.9700
C3—H99B0.953 (15)C6—H6B0.9700
C2—O2—C5118.29 (9)C6—C4—H4B108.9
C3—C1—C2121.28 (11)H4A—C4—H4B107.7
C3—C1—H99A123.9 (9)O2—C5—C6i109.82 (9)
C2—C1—H99A114.5 (9)O2—C5—H5A109.7
O1—C2—O2123.96 (11)C6i—C5—H5A109.7
O1—C2—C1125.48 (12)O2—C5—H5B109.7
O2—C2—C1110.49 (10)C6i—C5—H5B109.7
C1—C3—C4126.20 (11)H5A—C5—H5B108.2
C1—C3—H99B118.0 (8)C5i—C6—C4115.19 (11)
C4—C3—H99B115.8 (8)C5i—C6—H6A108.5
C3—C4—C6113.36 (10)C4—C6—H6A108.5
C3—C4—H4A108.9C5i—C6—H6B108.5
C6—C4—H4A108.9C4—C6—H6B108.5
C3—C4—H4B108.9H6A—C6—H6B107.5
C5—O2—C2—O16.53 (16)C2—C1—C3—C4173.80 (9)
C5—O2—C2—C1170.56 (8)C1—C3—C4—C6126.34 (13)
C3—C1—C2—O19.95 (18)C2—O2—C5—C6i118.97 (11)
C3—C1—C2—O2167.09 (9)C3—C4—C6—C5i71.46 (14)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1ii0.972.673.544 (2)150
Symmetry code: (ii) x+2, y+1, z.
 

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