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

Blaurock, S.; Fischer, A.; Gottfriedsen, J.; Spoida, M.; Edelmann, F.T.

doi:10.1107/S160053680802775X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1881

doi:10.1107/S160053680802775X

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

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

^aChemisches Institut, Otto-von-Guericke-Universität Magdeburg, Universitätsplatz 2, D-39106 Magdeburg, Germany
^*Correspondence e-mail: frank.edelmann@ovgu.de

(Received 9 July 2008; accepted 29 August 2008; online 6 September 2008)

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 ).

Experimental

Crystal data

C₉H₁₆O₂
M_r = 156.22
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 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

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)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

For related literature, see: Etter (1991); Brock & Duncan (1994); Fendrick et al. (1988).

Experimental top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule of the title compound in the crystal. Displacement ellipsoids represent 50% probability levels. H-Atom radii are arbitrary.
	Fig. 2. The hydrogen-bond network.

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

Crystal data top

C₉H₁₆O₂	F(000) = 688
M_r = 156.22	D_x = 1.142 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 5784 reflections
a = 13.006 (3) Å	θ = 2.5–30.0°
b = 10.5279 (16) Å	µ = 0.08 mm⁻¹
c = 13.892 (2) Å	T = 133 K
β = 107.257 (10)°	Plate, colourless
V = 1816.6 (6) Å³	0.45 × 0.28 × 0.07 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 30.5°, θ_min = 1.6°
Detector resolution: 8.192 pixels mm^-1	h = −18→18
ω–scans	k = −14→15
20936 measured reflections	l = −19→19
5532 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0812P)²] where P = (F_o² + 2F_c²)/3
5532 reflections	(Δ/σ)_max = 0.002
223 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₉H₁₆O₂	V = 1816.6 (6) Å³
M_r = 156.22	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.006 (3) Å	µ = 0.08 mm⁻¹
b = 10.5279 (16) Å	T = 133 K
c = 13.892 (2) Å	0.45 × 0.28 × 0.07 mm
β = 107.257 (10)°

Data collection top

Bruker SMART CCD diffractometer	3876 reflections with I > 2σ(I)
20936 measured reflections	R_int = 0.048
5532 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.41 e Å⁻³
5532 reflections	Δρ_min = −0.23 e Å⁻³
223 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.

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	U_iso*/U_eq
O1	0.16035 (7)	0.34338 (9)	0.59028 (7)	0.0255 (2)
O2	0.16763 (8)	0.21564 (10)	0.28457 (7)	0.0330 (3)
H02	0.2279 (16)	0.2415 (16)	0.3207 (14)	0.048 (5)*
H01	0.1585 (14)	0.3212 (17)	0.6560 (15)	0.055 (5)*
C1	0.08579 (10)	0.28972 (13)	0.41367 (9)	0.0260 (3)
H1A	0.0100	0.3172	0.3852	0.031*
H1B	0.1335	0.3623	0.4115	0.031*
C2	0.10655 (9)	0.24265 (12)	0.52290 (8)	0.0210 (2)
C3	0.17851 (9)	0.12814 (12)	0.52756 (9)	0.0217 (2)
C4	0.17849 (10)	0.09054 (12)	0.43564 (10)	0.0242 (3)
C5	0.11007 (10)	0.17648 (13)	0.35382 (9)	0.0260 (3)
C6	0.00335 (10)	0.20778 (14)	0.54767 (10)	0.0290 (3)
H6C	0.0216	0.1724	0.6159	0.035*
H6B	−0.0368	0.1446	0.4992	0.035*
H6A	−0.0410	0.2840	0.5438	0.035*
C7	0.23648 (11)	0.06809 (14)	0.62666 (10)	0.0312 (3)
H7C	0.2703	−0.0112	0.6148	0.037*
H7B	0.1851	0.0499	0.6641	0.037*
H7A	0.2920	0.1263	0.6659	0.037*
C8	0.23380 (13)	−0.02192 (15)	0.40823 (12)	0.0397 (4)
H8C	0.2779	−0.0635	0.4698	0.048*
H8B	0.2800	0.0058	0.3678	0.048*
H8A	0.1799	−0.0819	0.3691	0.048*
C9	0.00891 (12)	0.11076 (17)	0.28879 (11)	0.0403 (4)
H9C	−0.0333	0.1707	0.2385	0.048*
H9B	−0.0343	0.0814	0.3315	0.048*
H9A	0.0293	0.0379	0.2545	0.048*
O1'	0.34071 (7)	0.44079 (8)	0.55499 (7)	0.0229 (2)
H01'	0.2803 (14)	0.4165 (17)	0.5720 (13)	0.042 (5)*
O2'	0.63799 (7)	0.68485 (9)	0.61022 (7)	0.0229 (2)
H02'	0.6360 (15)	0.6373 (17)	0.5589 (15)	0.053 (5)*
C1'	0.48169 (9)	0.58556 (11)	0.64713 (8)	0.0188 (2)
H1'1	0.5235	0.5089	0.6413	0.023*
H1'2	0.4843	0.5963	0.7186	0.023*
C2'	0.36462 (9)	0.57287 (11)	0.58020 (9)	0.0183 (2)
C3'	0.36529 (9)	0.64743 (11)	0.48658 (9)	0.0195 (2)
C4'	0.45363 (9)	0.71901 (11)	0.50268 (8)	0.0190 (2)
C5'	0.52810 (9)	0.70382 (11)	0.60928 (8)	0.0182 (2)
C6'	0.28221 (10)	0.62512 (13)	0.62934 (10)	0.0258 (3)
H6'C	0.2096	0.6166	0.5823	0.031*
H6'B	0.2974	0.7149	0.6461	0.031*
H6'A	0.2869	0.5772	0.6910	0.031*
C7'	0.27255 (10)	0.63672 (14)	0.39236 (10)	0.0279 (3)
H7'C	0.2824	0.6968	0.3420	0.033*
H7'B	0.2054	0.6563	0.4076	0.033*
H7'A	0.2691	0.5501	0.3658	0.033*
C8'	0.48398 (11)	0.80742 (12)	0.43083 (10)	0.0269 (3)
H8'C	0.4254	0.8108	0.3674	0.032*
H8'B	0.5497	0.7766	0.4178	0.032*
H8'A	0.4966	0.8926	0.4604	0.032*
C9'	0.52987 (11)	0.82140 (12)	0.67418 (10)	0.0251 (3)
H9'C	0.5805	0.8079	0.7414	0.030*
H9'B	0.4576	0.8364	0.6801	0.030*
H9'A	0.5526	0.8953	0.6427	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0289 (5)	0.0282 (5)	0.0219 (4)	−0.0072 (4)	0.0112 (4)	−0.0031 (4)
O2	0.0267 (5)	0.0570 (7)	0.0158 (4)	−0.0163 (5)	0.0073 (4)	−0.0031 (4)
C1	0.0231 (6)	0.0341 (7)	0.0202 (6)	0.0010 (5)	0.0056 (5)	0.0049 (5)
C2	0.0199 (6)	0.0263 (6)	0.0171 (5)	−0.0033 (5)	0.0058 (4)	0.0005 (4)
C3	0.0188 (6)	0.0260 (6)	0.0205 (6)	−0.0037 (5)	0.0061 (5)	0.0017 (5)
C4	0.0226 (6)	0.0274 (6)	0.0243 (6)	−0.0055 (5)	0.0095 (5)	−0.0036 (5)
C5	0.0208 (6)	0.0402 (7)	0.0173 (6)	−0.0091 (5)	0.0061 (5)	−0.0010 (5)
C6	0.0216 (6)	0.0397 (8)	0.0278 (7)	−0.0046 (5)	0.0106 (5)	−0.0011 (5)
C7	0.0316 (7)	0.0343 (7)	0.0265 (7)	0.0029 (6)	0.0067 (6)	0.0063 (6)
C8	0.0442 (9)	0.0363 (8)	0.0449 (9)	0.0000 (7)	0.0229 (7)	−0.0084 (7)
C9	0.0297 (7)	0.0629 (11)	0.0264 (7)	−0.0213 (7)	0.0055 (6)	−0.0049 (7)
O1'	0.0221 (4)	0.0214 (4)	0.0278 (5)	−0.0045 (3)	0.0114 (4)	−0.0053 (3)
O2'	0.0167 (4)	0.0300 (5)	0.0219 (4)	−0.0034 (3)	0.0057 (3)	−0.0059 (4)
C1'	0.0199 (5)	0.0204 (5)	0.0160 (5)	−0.0008 (4)	0.0053 (4)	0.0006 (4)
C2'	0.0185 (5)	0.0182 (5)	0.0193 (5)	−0.0014 (4)	0.0074 (4)	−0.0025 (4)
C3'	0.0204 (5)	0.0211 (6)	0.0166 (5)	0.0036 (4)	0.0049 (4)	−0.0002 (4)
C4'	0.0227 (6)	0.0192 (5)	0.0161 (5)	0.0025 (4)	0.0071 (4)	0.0009 (4)
C5'	0.0171 (5)	0.0206 (6)	0.0175 (5)	−0.0010 (4)	0.0062 (4)	−0.0009 (4)
C6'	0.0249 (6)	0.0274 (6)	0.0288 (6)	−0.0009 (5)	0.0138 (5)	−0.0038 (5)
C7'	0.0250 (6)	0.0323 (7)	0.0215 (6)	0.0025 (5)	−0.0006 (5)	0.0001 (5)
C8'	0.0320 (7)	0.0270 (6)	0.0241 (6)	0.0014 (5)	0.0119 (5)	0.0067 (5)
C9'	0.0301 (6)	0.0237 (6)	0.0230 (6)	−0.0028 (5)	0.0101 (5)	−0.0054 (5)

Geometric parameters (Å, º) top

O1—C2	1.4498 (14)	O1'—C2'	1.4451 (14)
O1—H01	0.95 (2)	O1'—H01'	0.921 (18)
O2—C5	1.4434 (15)	O2'—C5'	1.4394 (14)
O2—H02	0.841 (19)	O2'—H02'	0.86 (2)
C1—C5	1.5388 (19)	C1'—C2'	1.5365 (16)
C1—C2	1.5421 (17)	C1'—C5'	1.5425 (16)
C1—H1A	0.9900	C1'—H1'1	0.9900
C1—H1B	0.9900	C1'—H1'2	0.9900
C2—C3	1.5157 (18)	C2'—C3'	1.5214 (16)
C2—C6	1.5259 (17)	C2'—C6'	1.5334 (17)
C3—C4	1.3369 (17)	C3'—C4'	1.3362 (17)
C3—C7	1.4992 (17)	C3'—C7'	1.4981 (17)
C4—C8	1.492 (2)	C4'—C8'	1.5007 (17)
C4—C5	1.5174 (19)	C4'—C5'	1.5184 (16)
C5—C9	1.5233 (18)	C5'—C9'	1.5275 (16)
C6—H6C	0.9800	C6'—H6'C	0.9800
C6—H6B	0.9800	C6'—H6'B	0.9800
C6—H6A	0.9800	C6'—H6'A	0.9800
C7—H7C	0.9800	C7'—H7'C	0.9800
C7—H7B	0.9800	C7'—H7'B	0.9800
C7—H7A	0.9800	C7'—H7'A	0.9800
C8—H8C	0.9800	C8'—H8'C	0.9800
C8—H8B	0.9800	C8'—H8'B	0.9800
C8—H8A	0.9800	C8'—H8'A	0.9800
C9—H9C	0.9800	C9'—H9'C	0.9800
C9—H9B	0.9800	C9'—H9'B	0.9800
C9—H9A	0.9800	C9'—H9'A	0.9800

C2—O1—H01	107.2 (11)	C2'—O1'—H01'	110.1 (11)
C5—O2—H02	105.7 (13)	C5'—O2'—H02'	106.6 (13)
C5—C1—C2	106.18 (10)	C2'—C1'—C5'	106.36 (9)
C5—C1—H1A	110.5	C2'—C1'—H1'1	110.5
C2—C1—H1A	110.5	C5'—C1'—H1'1	110.5
C5—C1—H1B	110.5	C2'—C1'—H1'2	110.5
C2—C1—H1B	110.5	C5'—C1'—H1'2	110.5
H1A—C1—H1B	108.7	H1'1—C1'—H1'2	108.6
O1—C2—C3	112.37 (10)	O1'—C2'—C3'	110.16 (9)
O1—C2—C6	108.58 (10)	O1'—C2'—C6'	108.94 (10)
C3—C2—C6	111.86 (10)	C3'—C2'—C6'	112.18 (10)
O1—C2—C1	108.08 (10)	O1'—C2'—C1'	109.49 (9)
C3—C2—C1	102.90 (10)	C3'—C2'—C1'	102.50 (9)
C6—C2—C1	112.97 (10)	C6'—C2'—C1'	113.42 (10)
C4—C3—C7	127.58 (12)	C4'—C3'—C7'	128.18 (11)
C4—C3—C2	111.69 (11)	C4'—C3'—C2'	111.76 (10)
C7—C3—C2	120.70 (11)	C7'—C3'—C2'	120.05 (11)
C3—C4—C8	127.96 (13)	C3'—C4'—C8'	128.40 (11)
C3—C4—C5	111.89 (11)	C3'—C4'—C5'	111.83 (10)
C8—C4—C5	120.13 (12)	C8'—C4'—C5'	119.76 (10)
O2—C5—C4	111.39 (11)	O2'—C5'—C4'	111.58 (9)
O2—C5—C9	105.18 (10)	O2'—C5'—C9'	105.43 (9)
C4—C5—C9	112.63 (12)	C4'—C5'—C9'	112.58 (10)
O2—C5—C1	111.66 (11)	O2'—C5'—C1'	111.89 (9)
C4—C5—C1	103.06 (10)	C4'—C5'—C1'	102.51 (9)
C9—C5—C1	113.13 (12)	C9'—C5'—C1'	113.06 (10)
C2—C6—H6C	109.5	C2'—C6'—H6'C	109.5
C2—C6—H6B	109.5	C2'—C6'—H6'B	109.5
H6C—C6—H6B	109.5	H6'C—C6'—H6'B	109.5
C2—C6—H6A	109.5	C2'—C6'—H6'A	109.5
H6C—C6—H6A	109.5	H6'C—C6'—H6'A	109.5
H6B—C6—H6A	109.5	H6'B—C6'—H6'A	109.5
C3—C7—H7C	109.5	C3'—C7'—H7'C	109.5
C3—C7—H7B	109.5	C3'—C7'—H7'B	109.5
H7C—C7—H7B	109.5	H7'C—C7'—H7'B	109.5
C3—C7—H7A	109.5	C3'—C7'—H7'A	109.5
H7C—C7—H7A	109.5	H7'C—C7'—H7'A	109.5
H7B—C7—H7A	109.5	H7'B—C7'—H7'A	109.5
C4—C8—H8C	109.5	C4'—C8'—H8'C	109.5
C4—C8—H8B	109.5	C4'—C8'—H8'B	109.5
H8C—C8—H8B	109.5	H8'C—C8'—H8'B	109.5
C4—C8—H8A	109.5	C4'—C8'—H8'A	109.5
H8C—C8—H8A	109.5	H8'C—C8'—H8'A	109.5
H8B—C8—H8A	109.5	H8'B—C8'—H8'A	109.5
C5—C9—H9C	109.5	C5'—C9'—H9'C	109.5
C5—C9—H9B	109.5	C5'—C9'—H9'B	109.5
H9C—C9—H9B	109.5	H9'C—C9'—H9'B	109.5
C5—C9—H9A	109.5	C5'—C9'—H9'A	109.5
H9C—C9—H9A	109.5	H9'C—C9'—H9'A	109.5
H9B—C9—H9A	109.5	H9'B—C9'—H9'A	109.5

C5—C1—C2—O1	139.28 (10)	C5'—C1'—C2'—O1'	138.54 (9)
C5—C1—C2—C3	20.24 (12)	C5'—C1'—C2'—C3'	21.61 (11)
C5—C1—C2—C6	−100.55 (12)	C5'—C1'—C2'—C6'	−99.55 (11)
O1—C2—C3—C4	−130.31 (11)	O1'—C2'—C3'—C4'	−130.65 (11)
C6—C2—C3—C4	107.25 (12)	C6'—C2'—C3'—C4'	107.81 (12)
C1—C2—C3—C4	−14.31 (13)	C1'—C2'—C3'—C4'	−14.19 (13)
O1—C2—C3—C7	51.62 (15)	O1'—C2'—C3'—C7'	50.55 (14)
C6—C2—C3—C7	−70.82 (14)	C6'—C2'—C3'—C7'	−70.99 (14)
C1—C2—C3—C7	167.63 (11)	C1'—C2'—C3'—C7'	167.00 (10)
C7—C3—C4—C8	1.6 (2)	C7'—C3'—C4'—C8'	−0.3 (2)
C2—C3—C4—C8	−176.35 (12)	C2'—C3'—C4'—C8'	−178.94 (11)
C7—C3—C4—C5	−179.83 (12)	C7'—C3'—C4'—C5'	179.35 (11)
C2—C3—C4—C5	2.27 (15)	C2'—C3'—C4'—C5'	0.67 (14)
C3—C4—C5—O2	130.67 (12)	C3'—C4'—C5'—O2'	133.00 (10)
C8—C4—C5—O2	−50.59 (16)	C8'—C4'—C5'—O2'	−47.36 (14)
C3—C4—C5—C9	−111.43 (13)	C3'—C4'—C5'—C9'	−108.69 (12)
C8—C4—C5—C9	67.31 (16)	C8'—C4'—C5'—C9'	70.96 (14)
C3—C4—C5—C1	10.82 (14)	C3'—C4'—C5'—C1'	13.10 (13)
C8—C4—C5—C1	−170.44 (12)	C8'—C4'—C5'—C1'	−167.25 (10)
C2—C1—C5—O2	−138.72 (10)	C2'—C1'—C5'—O2'	−140.96 (9)
C2—C1—C5—C4	−19.06 (12)	C2'—C1'—C5'—C4'	−21.28 (11)
C2—C1—C5—C9	102.85 (12)	C2'—C1'—C5'—C9'	100.18 (11)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₆O₂
M_r	156.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	133
a, b, c (Å)	13.006 (3), 10.5279 (16), 13.892 (2)
β (°)	107.257 (10)
V (Å³)	1816.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.28 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20936, 5532, 3876
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.142, 1.03
No. of reflections	5532
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP5 in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Brock, C. P. & Duncan, L. L. (1994). Chem. Mater. 6, 1307–1312. CrossRef CAS Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Etter, M. C. (1991). J. Phys. Chem. 95, 4601–4610. CrossRef CAS Web of Science Google Scholar
Fendrick, C. M., Schertz, L. D., Day, V. W. & Marks, T. J. (1988). Organometallics, 7, 1828–1838. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar