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
CCDC reference: 601093
Key indicators
- Single-crystal X-ray study
- T = 301 K
- Mean (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
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
C12H16O4 | Z = 1 |
Mr = 224.25 | F(000) = 120 |
Triclinic, P1 | Dx = 1.272 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.442 (3) Å | Cell parameters from 938 reflections |
b = 6.665 (3) Å | θ = 28.3–0.9° |
c = 7.757 (4) Å | µ = 0.10 mm−1 |
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 tube | 1278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 28.3°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −8→8 |
Tmin = 0.754, Tmax = 0.984 | k = −8→8 |
5226 measured reflections | l = −10→10 |
Refinement top
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)] = 0.042 | H 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 reflections | Δρmax = 0.20 e Å−3 |
82 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O2 | 0.33098 (13) | 0.81151 (13) | −0.11673 (10) | 0.0483 (3) | |
C1 | 0.59655 (19) | 0.72251 (16) | 0.07816 (15) | 0.0446 (3) | |
C2 | 0.55029 (19) | 0.77086 (17) | −0.11113 (15) | 0.0454 (3) | |
C3 | 0.7891 (2) | 0.71892 (17) | 0.11454 (15) | 0.0465 (3) | |
O1 | 0.68569 (16) | 0.7824 (2) | −0.24410 (12) | 0.0713 (3) | |
C4 | 0.8471 (2) | 0.69366 (19) | 0.29840 (16) | 0.0537 (3) | |
H4A | 0.9627 | 0.5508 | 0.3339 | 0.064* | |
H4B | 0.7154 | 0.6932 | 0.3866 | 0.064* | |
C5 | 0.2471 (2) | 0.8963 (2) | −0.29373 (16) | 0.0558 (3) | |
H5A | 0.1837 | 0.7937 | −0.3114 | 0.067* | |
H5B | 0.3698 | 0.9086 | −0.3893 | 0.067* | |
C6 | 0.9303 (2) | 0.8781 (2) | 0.30483 (17) | 0.0551 (3) | |
H6A | 0.9970 | 0.8329 | 0.4174 | 0.066* | |
H6B | 1.0477 | 0.8923 | 0.2047 | 0.066* | |
H99A | 0.473 (2) | 0.712 (2) | 0.167 (2) | 0.058 (4)* | |
H99B | 0.903 (2) | 0.736 (2) | 0.0155 (19) | 0.056 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0550 (5) | 0.0481 (4) | 0.0446 (4) | −0.0188 (3) | −0.0124 (3) | −0.0087 (3) |
C1 | 0.0498 (6) | 0.0361 (5) | 0.0437 (5) | −0.0097 (4) | −0.0075 (5) | −0.0080 (4) |
C2 | 0.0514 (6) | 0.0372 (5) | 0.0472 (6) | −0.0100 (4) | −0.0076 (5) | −0.0142 (4) |
C3 | 0.0499 (6) | 0.0390 (5) | 0.0454 (6) | −0.0070 (4) | −0.0080 (5) | −0.0108 (4) |
O1 | 0.0604 (6) | 0.1010 (8) | 0.0499 (5) | −0.0190 (5) | −0.0001 (4) | −0.0284 (5) |
C4 | 0.0597 (7) | 0.0478 (6) | 0.0483 (6) | −0.0105 (5) | −0.0186 (5) | −0.0051 (5) |
C5 | 0.0686 (8) | 0.0579 (7) | 0.0480 (6) | −0.0211 (6) | −0.0186 (5) | −0.0142 (5) |
C6 | 0.0546 (7) | 0.0628 (7) | 0.0495 (6) | −0.0173 (5) | −0.0195 (5) | −0.0094 (5) |
Geometric parameters (Å, º) top
O2—C2 | 1.3449 (15) | C4—C6 | 1.5281 (19) |
O2—C5 | 1.4528 (14) | C4—H4A | 0.9700 |
C1—C3 | 1.3201 (18) | C4—H4B | 0.9700 |
C1—C2 | 1.4742 (16) | C5—C6i | 1.5069 (19) |
C1—H99A | 0.942 (15) | C5—H5A | 0.9700 |
C2—O1 | 1.2027 (15) | C5—H5B | 0.9700 |
C3—C4 | 1.4952 (16) | C6—H6A | 0.9700 |
C3—H99B | 0.953 (15) | C6—H6B | 0.9700 |
| | | |
C2—O2—C5 | 118.29 (9) | C6—C4—H4B | 108.9 |
C3—C1—C2 | 121.28 (11) | H4A—C4—H4B | 107.7 |
C3—C1—H99A | 123.9 (9) | O2—C5—C6i | 109.82 (9) |
C2—C1—H99A | 114.5 (9) | O2—C5—H5A | 109.7 |
O1—C2—O2 | 123.96 (11) | C6i—C5—H5A | 109.7 |
O1—C2—C1 | 125.48 (12) | O2—C5—H5B | 109.7 |
O2—C2—C1 | 110.49 (10) | C6i—C5—H5B | 109.7 |
C1—C3—C4 | 126.20 (11) | H5A—C5—H5B | 108.2 |
C1—C3—H99B | 118.0 (8) | C5i—C6—C4 | 115.19 (11) |
C4—C3—H99B | 115.8 (8) | C5i—C6—H6A | 108.5 |
C3—C4—C6 | 113.36 (10) | C4—C6—H6A | 108.5 |
C3—C4—H4A | 108.9 | C5i—C6—H6B | 108.5 |
C6—C4—H4A | 108.9 | C4—C6—H6B | 108.5 |
C3—C4—H4B | 108.9 | H6A—C6—H6B | 107.5 |
| | | |
C5—O2—C2—O1 | −6.53 (16) | C2—C1—C3—C4 | 173.80 (9) |
C5—O2—C2—C1 | 170.56 (8) | C1—C3—C4—C6 | −126.34 (13) |
C3—C1—C2—O1 | 9.95 (18) | C2—O2—C5—C6i | −118.97 (11) |
C3—C1—C2—O2 | −167.09 (9) | C3—C4—C6—C5i | 71.46 (14) |
Symmetry code: (i) −x+1, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1ii | 0.97 | 2.67 | 3.544 (2) | 150 |
Symmetry code: (ii) −x+2, −y+1, −z. |