1,2,3,4-Tetra­methyl­cyclo­pent-2-ene-1,4-diol

Steffen Blaurock; Axel Fischer; Jochen Gottfriedsen; Marlies Spoida; Frank T Edelmann

doi:10.1107/S160053680802775X

. 2008 Sep 6;64(Pt 10):o1881. doi: 10.1107/S160053680802775X

1,2,3,4-Tetramethylcyclopent-2-ene-1,4-diol

Steffen Blaurock ^a, Axel Fischer ^a, Jochen Gottfriedsen ^a, Marlies Spoida ^a, Frank T Edelmann ^a,^*

PMCID: PMC2959352 PMID: 21201094

Abstract

The title compound, C₉H₁₆O₂, crystallizes with two molecules in the asymmetric unit. The structure displays intermolecular O—H⋯O hydrogen bonding.

Related literature

For related literature, see: Etter (1991 ▶); Brock & Duncan (1994 ▶); Fendrick et al. (1988 ▶). graphic file with name e-64-o1881-scheme1.jpg

Experimental

Crystal data

C₉H₁₆O₂
M _r = 156.22
Monoclinic,
a = 13.006 (3) Å
b = 10.5279 (16) Å
c = 13.892 (2) Å
β = 107.257 (10)°
V = 1816.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 133 (2) K
0.45 × 0.28 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
20936 measured reflections
5532 independent reflections
3876 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.142
S = 1.03
5532 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP5 in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802775X/bt2745sup1.cif

e-64-o1881-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802775X/bt2745Isup2.hkl

e-64-o1881-Isup2.hkl^{(270.9KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H01⋯O2ⁱ	0.95 (2)	1.80 (2)	2.7438 (13)	174.7 (17)
O1′—H01′⋯O1	0.921 (18)	1.824 (18)	2.7345 (13)	169.3 (16)
O2—H02⋯O2′ⁱⁱ	0.841 (19)	1.89 (2)	2.7263 (13)	173.0 (18)
O2′—H02′⋯O1′ⁱⁱ	0.86 (2)	1.89 (2)	2.7333 (13)	166.1 (18)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Financial support by the Otto-von-Guericke-Universität Magdeburg is gratefully acknowledged.

supplementary crystallographic information

Comment

In the solid state, alcohols generally form hydrogen-bonded networks resulting in a variety of ring, chain, or helix structures (Brock & Duncan, 1994). The hitherto unknown title compound, 1,2,3,4-tetramethylcyclopen-2-ene-1,4-diol, was obtained in minor quantities (less than 5% isolated yield) in the form of colorless crystals during a preparation of 1,2,3,4-tetramethylcyclopentadiene according to the literature (Fendrick et al., 1988). The structure of the title compound is shown in Figure 1. Dimensions are available in the archived CIF. Especially notable is the hydrogen-bond network in the crystal structure. As depicted in Figure 2, four molecules of 1,2,3,4-tetramethylcyclopen-2-ene-1,4-diol are connected via hydrogen-bonds to give cyclic tetramers. Further hydrogen-bonding between adjacent tetrameric units results in an extended hydrogen-bond network.

Experimental

Crystals of the title compound were obtained as a minor by-product during the synthesis of 1,2,3,4-tetramethylcyclopentadiene according to the literature preparatio (Fendrick et al., 1988).