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In the title compound, C13H22O3, the asymmetric unit has two independent mol­ecules linked by a strong O-H...O hydrogen bond. The cyclo­hexane ring is trans fused to the cyclo­pentane ring bridged through an ethyl moiety. The hydroxyl groups act as donors as well as acceptors, resulting in an extensive two-dimensional hydrogen-bonded network in the (011) plane. Intermolecular O-H...O bonds between centrosymmetrically related mol­ecules form a four-membered supramolecular assembly, leading to infinite chains parallel to the [01\overline 1] direction, crosslinked in the [100] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102010843/sk1554sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010843/sk1554IIsup2.hkl
Contains datablock II

CCDC reference: 193424

Comment top

Khusimone, (I), a norsesquiterpene ketone containing a tricyclo[6.2.1.01,5]undecane skeleton, is one of the main olfactively important constituents of vetiver oil (Büchi et al., 1977). In connection with our studies directed towards the synthesis and characterization of bridged ring systems related to tricyclic sesquiterpenes (Das et al., 1996; Pati et al., 2000), the title tricyclic triol, (II), has been synthesized. This triol possesses the requisite structural features for a potential intermediate in a total synthesis of khusimone. The structure determination of (II) was undertaken in order to establish the relative stereochemistries of the five asymmetric centres (C1, C2, C5, C6 and C8), and to devise the subsequent sequence of reactions leading to the total synthesis of (I). \sch

Compound (II) consists of a cyclohexane ring trans fused to a cyclopentane ring bridged via an ethyl moiety. The asymmetric unit of (II) contains two crystallographically independent molecules, A and B (Fig. 1), with almost similar geometries. Equivalent bond distances and angles in the two molecules agree within experimental limits. In both molecules, the torsion angles (Table 1) about the C2A—C3A, C4A—C5A, C2B—C3B and C4B—C5B bonds indicate the equatorial orientations of the two hydroxyl groups at the C2 and C5 positions, while the axial orientation of the OH group at the ring junction C atom (C6A and C6B) is evident from the torsion angles about the C5A—C6A and C5B—C6B bonds.

The two methyl groups at C7A and C7B are in almost syn-periplanar and gauche orientations with respect to the C6A—O3A and C6B—O3B bonds [O3A—C6A—C7A—C12A -12.1 (3), O3B—C6B—C7B—C12B 14.5 (3), O3A—C6A—C7A—C13A -134.7 (3) and O3B—O6B—C7B—C13B 135.9 (2)°].

The C—C [1.515 (4)–1.596 (4) Å] and C—O [1.433 (3)–1.449 (3) Å] bond distances agree well with the corresponding values reported in the literature (Allen et al., 1987). The lengthening of the C3C—CC2O bond distances [C6A—C7A 1.596 (4) Å in molecule A and C6B—C7B 1.589 (4) Å in molecule B] compared with other C—C bond lengths (Table 1) is consistant with observations in related tricycloundecane structures (Pati et al., 2002).

The C1—C6 cyclohexane ring displays a chair conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.586 (3) Å, q2 = 0.051 (3) Å, q3 = -0.584 (3) Å and θ = 175.1 (3)° for molecule A, and Q = 0.579 (3) Å, q2 = 0.060 (3) Å, q3 = 0.576 (3) Å and θ = 5.9 (3)° for molecule B. The cyclopentane ring (C1/C6/C7/C8/C11) adopts an almost envelope conformation, with atom C11 deviating by 0.877 (4) Å in both molecules A and B from the least-squares plane through the remaining endocyclic atoms.

The dihedral angles between the planar parts of the fused cyclohexane and cyclopentane rings are 16.3 (2)° in molecule A and 18.2 (1)° in molecule B. The other five-membered ring (C1/C10/C8/C9/C11), with ring puckering parameters q2 = 0.606 (3) Å and ϕ = -43.4 (3)° (for molecule A) and q2 = 0.613 (3) Å and ϕ = 136.4 (3)° (for molecule B), also assumes a distorted envelope conformation, with atom C11 displaced from the ring plane by 0.884 (4) Å in molecule A and 0.887 (4) Å in molecule B. The molecule of (II) has five chiral centres (C1, C2, C5, C6 and C8) and, from the centrosymmetric space group, it follows that the crystal is a racemate.

Intramolecular O—H···O hydrogen bonds (Table 2) influence the conformation of the two independent molecules of (II), A and B. In addition, each hydroxyl group in the molecule acts as a potential donor as well as an acceptor in an extensive intermolecular hydrogen-bond network. The resulting hydrogen-bonded supramolecular structure is of considerable complexity. A similar supramolecular network, solely controlled by hydrogen bonds between hydroxyl groups, has been reported by Deák et al. (2001).

A simplified description of the supramolecular assembly in (II), in terms of tetramolecular motifs leading to parallel chains and the connections between such chains, can be visualized as follows. The two molecules in the asymmetric unit, A and B, are linked via a strong O1A—H1A···O1B(x, y, z) hydrogen bond (Table 2 and Fig. 1). The intermolecular O—H···O hydrogen bonds between the molecules in the asymmetric unit and their centrosymmetrically related counterparts, O2B-H2B1···O1A(1 - x, 1 - y, 1 - z), result in the formation of a four-membered A2B2 aggregate in the structure (Fig. 2). These supramolecular A2B2 units, connected through O2A-H2A1···O2B(x, y - 1, 1 + z) hydrogen bonds, give rise to infinite ABAB··· chains parallel to the [011] direction (Fig. 3). These chains are interlinked by O3A—H3A···O2A(2 - x, -y, 2 - z), O1B—H1B···O3B(2 - x, 1 - y, 1 - z) and O3B—H3B···O3A(2 - x, 1 - y, 1 - z) hydrogen bonds to complete the two-dimensional supramolecular network in the (011) plane.

Experimental top

A solution of (1RS,2RS,8RS)-2-hydroxy-7,7-dimethyltricyclo[6.2.1.01,6]undec-5-ene (0.31 g, 1.6 mmol) and OsO4 (0.41 g, 1.6 mmol) in pyridine (6 ml) was stored at room temperature for 5 d. A saturated aqueous solution of sodium hydrogen sulfite (20 ml) was then added to the reaction mixture, and stirring was continued at room temperature for 3 h. Water (20 ml) was added and the product was extracted with ether. The ether extract was washed with dilute HCl and then water, and then dried. The residue remaining upon evaporation of the solvent was crystallized from a mixture of ether and light petroleum (1:1) to furnish the title triol, (II) (0.3 g, 82%) (m.p. 451–453 K). Elemental analysis, calculated for C13H22O3, requires: C 68.99, H 9.80%; found: C 68.85, H 9.92%.

Refinement top

H atoms were placed geometrically and were treated as riding using the appropriate instructions in SHELXL97 (Sheldrick, 1997). The hydroxyl H atoms were constrained using the HFIX 147 instruction, with the O—H distances fixed at 0.82 Å and the C—O—H angles tetrahedral; for the idealized methyl groups, the HFIX 137 instruction was used, with C—H = 0.96–0.98 Å. Please check added constraints.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995) and WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. A view of the structure of (II), with displacement ellipsoids at the 50% probability level, showing the two independent molecules connected by O—H···O interactions. H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The four-membered supramolecular aggregates of (II) [symmetry code: (i) 1 - x, 1 - y, 1 - z]. H atoms bonded to C atoms have been omitted for the sake of clarity.
[Figure 3] Fig. 3. A packing diagram for (II) viewed down the c axis. Hydrogen bonds are indicated by dotted lines. Atoms marked with a dollar sign (add), hash (#) or asterisk (*) are at the symmetry positions (1 - x, 1 - y, 1 - z), (x, y - 1, 1 + z) and (2 - x, 1 - y, 1 - z), respectively. H atoms bonded to C atoms have been omitted for the sake of clarity.
(1SR,2RS,5RS,6SR,8RS)-7,7-dimethyltricyclo[6.2.1.01,6]undecane-2,5,6-triol top
Crystal data top
C13H22O3Z = 4
Mr = 226.31F(000) = 496
Triclinic, P1Dx = 1.241 Mg m3
Hall symbol: -P 1Melting point: 453K K
a = 9.812 (2) ÅMo Kα radiation, λ = 0.71070 Å
b = 11.141 (1) ÅCell parameters from 18 reflections
c = 11.443 (2) Åθ = 6.9–8.1°
α = 82.47 (1)°µ = 0.09 mm1
β = 77.56 (1)°T = 293 K
γ = 89.46 (1)°Block, colourless
V = 1210.8 (3) Å30.5 × 0.4 × 0.3 mm
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.015
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.8°
Graphite monochromatorh = 1111
ω/2θ scansk = 130
4499 measured reflectionsl = 1313
4259 independent reflections3 standard reflections every 150 reflections
2972 reflections with I > 2σ(I) intensity decay: 1.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters not refined
S = 1.10 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.9623P]
where P = (Fo2 + 2Fc2)/3
4259 reflections(Δ/σ)max = 0.014
299 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C13H22O3γ = 89.46 (1)°
Mr = 226.31V = 1210.8 (3) Å3
Triclinic, P1Z = 4
a = 9.812 (2) ÅMo Kα radiation
b = 11.141 (1) ŵ = 0.09 mm1
c = 11.443 (2) ÅT = 293 K
α = 82.47 (1)°0.5 × 0.4 × 0.3 mm
β = 77.56 (1)°
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.015
4499 measured reflections3 standard reflections every 150 reflections
4259 independent reflections intensity decay: 1.1%
2972 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.156H-atom parameters not refined
S = 1.10Δρmax = 0.24 e Å3
4259 reflectionsΔρmin = 0.21 e Å3
299 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.7141 (3)0.2593 (2)0.9184 (2)0.0303 (6)
C2A0.6901 (3)0.2018 (2)0.8106 (2)0.0336 (6)
H2A0.77960.19780.75350.040*
C3A0.6296 (3)0.0742 (3)0.8510 (3)0.0410 (7)
H3A10.62220.03700.78060.049*
H3A20.53630.07840.90020.049*
C4A0.7192 (3)0.0050 (2)0.9236 (3)0.0383 (7)
H4A10.67250.08280.95310.046*
H4A20.80780.01910.87090.046*
C5A0.7465 (3)0.0526 (2)1.0304 (2)0.0306 (6)
H5A0.65790.05961.08800.037*
C6A0.8121 (3)0.1796 (2)0.9847 (2)0.0281 (6)
C7A0.8437 (3)0.2627 (3)1.0796 (2)0.0383 (7)
C8A0.7786 (3)0.3848 (3)1.0373 (3)0.0409 (7)
H8A0.82280.45621.05610.049*
C9A0.6201 (3)0.3799 (3)1.0801 (3)0.0490 (8)
H9A10.57970.45781.06080.059*
H9A20.59260.35451.16640.059*
C10A0.5768 (3)0.2844 (3)1.0080 (3)0.0396 (7)
H10A0.50620.31570.96510.048*
H10B0.54080.21131.06100.048*
C11A0.7907 (3)0.3824 (2)0.9017 (2)0.0363 (7)
H11A0.88660.38080.85730.044*
H11B0.74170.44810.86510.044*
C12A1.0010 (3)0.2824 (3)1.0680 (3)0.0561 (9)
H12A1.04220.31900.98750.084*
H12B1.04350.20581.08430.084*
H12C1.01560.33451.12480.084*
C13A0.7803 (4)0.2134 (3)1.2117 (3)0.0587 (10)
H13A0.68360.19271.22000.088*
H13B0.78820.27421.26230.088*
H13C0.82940.14261.23550.088*
O1A0.59473 (19)0.2694 (2)0.74991 (18)0.0453 (5)
H1A0.63690.32550.70290.068*
O2A0.84002 (19)0.01982 (17)1.08956 (18)0.0385 (5)
H2A10.79730.07871.13160.058*
O3A0.93661 (17)0.16502 (17)0.89587 (15)0.0319 (4)
H3A0.98610.11470.92450.048*
C1B0.7940 (3)0.6323 (2)0.5335 (2)0.0300 (6)
C2B0.8156 (3)0.5029 (2)0.5043 (2)0.0330 (6)
H2B0.90740.49770.45090.040*
C3B0.7034 (3)0.4690 (2)0.4412 (3)0.0359 (6)
H3B10.61330.46720.49670.043*
H3B20.72050.38840.41860.043*
C4B0.6993 (3)0.5582 (3)0.3280 (3)0.0396 (7)
H4B10.78350.54990.26730.048*
H4B20.62030.53720.29560.048*
C5B0.6875 (3)0.6889 (2)0.3516 (2)0.0313 (6)
H5B0.59610.69920.40390.038*
C6B0.8003 (2)0.7213 (2)0.4158 (2)0.0280 (6)
C7B0.7980 (3)0.8496 (2)0.4626 (3)0.0362 (7)
C8B0.8150 (3)0.8138 (3)0.5955 (3)0.0426 (7)
H8B0.85960.87720.62690.051*
C9B0.6780 (3)0.7643 (3)0.6783 (3)0.0531 (9)
H9B10.60230.82000.67270.064*
H9B20.68670.74800.76170.064*
C10B0.6553 (3)0.6465 (3)0.6274 (3)0.0387 (7)
H10C0.57620.65300.58870.046*
H10D0.63930.57810.69090.046*
C11B0.8977 (3)0.6965 (3)0.5892 (2)0.0391 (7)
H11C0.90490.65650.66820.047*
H11D0.98960.70820.53650.047*
C12B0.9221 (3)0.9312 (3)0.3914 (3)0.0434 (7)
H12D1.00790.89420.40260.065*
H12E0.91551.00870.42010.065*
H12F0.92030.94170.30710.065*
C13B0.6646 (3)0.9206 (3)0.4549 (3)0.0571 (9)
H13D0.66350.99080.49560.086*
H13E0.58450.87000.49270.086*
H13F0.66250.94530.37180.086*
O1B0.8074 (2)0.41898 (19)0.61185 (18)0.0459 (6)
H1B0.88560.39470.61560.069*
O2B0.6974 (2)0.76823 (19)0.23988 (18)0.0438 (5)
H2B10.62200.76900.21990.066*
O3B0.93444 (17)0.70004 (17)0.33988 (16)0.0320 (4)
H3B0.94590.74660.27670.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0273 (13)0.0295 (14)0.0315 (14)0.0018 (11)0.0054 (11)0.0037 (11)
C2A0.0269 (14)0.0401 (16)0.0325 (14)0.0007 (12)0.0084 (11)0.0033 (12)
C3A0.0406 (16)0.0428 (17)0.0409 (17)0.0081 (13)0.0133 (13)0.0019 (13)
C4A0.0371 (16)0.0312 (15)0.0445 (17)0.0042 (12)0.0060 (13)0.0019 (13)
C5A0.0257 (13)0.0296 (14)0.0328 (14)0.0024 (11)0.0027 (11)0.0031 (11)
C6A0.0261 (13)0.0300 (14)0.0249 (13)0.0015 (11)0.0016 (10)0.0018 (11)
C7A0.0480 (17)0.0338 (15)0.0349 (15)0.0013 (13)0.0119 (13)0.0068 (12)
C8A0.0490 (18)0.0320 (16)0.0428 (17)0.0007 (13)0.0105 (14)0.0076 (13)
C9A0.055 (2)0.0422 (18)0.0481 (18)0.0172 (15)0.0045 (15)0.0102 (15)
C10A0.0314 (15)0.0378 (16)0.0446 (17)0.0053 (12)0.0009 (13)0.0004 (13)
C11A0.0376 (16)0.0318 (15)0.0367 (15)0.0021 (12)0.0067 (12)0.0037 (12)
C12A0.058 (2)0.056 (2)0.067 (2)0.0009 (17)0.0346 (18)0.0182 (18)
C13A0.097 (3)0.0470 (19)0.0328 (17)0.0111 (19)0.0162 (18)0.0059 (14)
O1A0.0314 (11)0.0587 (14)0.0440 (12)0.0064 (9)0.0166 (9)0.0144 (10)
O2A0.0324 (10)0.0347 (11)0.0427 (11)0.0016 (8)0.0055 (9)0.0120 (9)
O3A0.0251 (9)0.0370 (11)0.0300 (10)0.0044 (8)0.0032 (8)0.0045 (8)
C1B0.0242 (13)0.0374 (15)0.0271 (13)0.0014 (11)0.0049 (11)0.0000 (11)
C2B0.0262 (13)0.0340 (15)0.0342 (14)0.0005 (11)0.0033 (11)0.0067 (12)
C3B0.0363 (15)0.0290 (14)0.0426 (16)0.0040 (12)0.0084 (13)0.0047 (12)
C4B0.0429 (17)0.0405 (17)0.0394 (16)0.0067 (13)0.0183 (13)0.0040 (13)
C5B0.0286 (14)0.0351 (15)0.0296 (14)0.0008 (11)0.0094 (11)0.0030 (11)
C6B0.0220 (13)0.0332 (14)0.0275 (13)0.0007 (11)0.0035 (10)0.0023 (11)
C7B0.0359 (15)0.0307 (15)0.0418 (16)0.0041 (12)0.0072 (13)0.0058 (12)
C8B0.0457 (18)0.0488 (18)0.0337 (15)0.0103 (14)0.0038 (13)0.0145 (13)
C9B0.055 (2)0.059 (2)0.0406 (18)0.0038 (16)0.0060 (15)0.0172 (16)
C10B0.0327 (15)0.0457 (17)0.0336 (15)0.0046 (13)0.0003 (12)0.0023 (13)
C11B0.0366 (15)0.0540 (19)0.0258 (14)0.0103 (13)0.0080 (12)0.0011 (13)
C12B0.0503 (18)0.0342 (16)0.0468 (18)0.0105 (13)0.0133 (14)0.0040 (13)
C13B0.053 (2)0.0416 (19)0.079 (2)0.0132 (15)0.0128 (18)0.0182 (18)
O1B0.0318 (11)0.0540 (13)0.0431 (12)0.0025 (10)0.0043 (9)0.0194 (10)
O2B0.0408 (12)0.0500 (13)0.0408 (11)0.0068 (10)0.0198 (9)0.0126 (9)
O3B0.0263 (9)0.0381 (11)0.0277 (10)0.0012 (8)0.0020 (8)0.0033 (8)
Geometric parameters (Å, º) top
C1A—C2A1.524 (4)C1B—C2B1.524 (4)
C1A—C11A1.539 (4)C1B—C11B1.538 (4)
C1A—C6A1.552 (3)C1B—C6B1.555 (3)
C1A—C10A1.555 (4)C1B—C10B1.562 (4)
C2A—O1A1.434 (3)C2B—O1B1.433 (3)
C2A—C3A1.521 (4)C2B—C3B1.517 (4)
C2A—H2A0.9800C2B—H2B0.9800
C3A—C4A1.533 (4)C3B—C4B1.533 (4)
C3A—H3A10.9700C3B—H3B10.9700
C3A—H3A20.9700C3B—H3B20.9700
C4A—C5A1.525 (4)C4B—C5B1.515 (4)
C4A—H4A10.9700C4B—H4B10.9700
C4A—H4A20.9700C4B—H4B20.9700
C5A—O2A1.436 (3)C5B—O2B1.441 (3)
C5A—C6A1.539 (3)C5B—C6B1.523 (4)
C5A—H5A0.9800C5B—H5B0.9800
C6A—O3A1.434 (3)C6B—O3B1.449 (3)
C6A—C7A1.596 (4)C6B—C7B1.589 (4)
C7A—C12A1.536 (4)C7B—C13B1.535 (4)
C7A—C13A1.535 (4)C7B—C12B1.541 (4)
C7A—C8A1.561 (4)C7B—C8B1.565 (4)
C8A—C9A1.526 (4)C8B—C9B1.529 (4)
C8A—C11A1.535 (4)C8B—C11B1.534 (4)
C8A—H8A0.9800C8B—H8B0.9800
C9A—C10A1.543 (4)C9B—C10B1.541 (4)
C9A—H9A10.9700C9B—H9B10.9700
C9A—H9A20.9700C9B—H9B20.9700
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—H13A0.9600C13B—H13D0.9600
C13A—H13B0.9600C13B—H13E0.9600
C13A—H13C0.9600C13B—H13F0.9600
O1A—H1A0.8200O1B—H1B0.8200
O2A—H2A10.8200O2B—H2B10.8200
O3A—H3A0.8200O3B—H3B0.8200
C2A—C1A—C11A121.4 (2)C2B—C1B—C11B121.8 (2)
C2A—C1A—C6A110.0 (2)C2B—C1B—C6B110.2 (2)
C11A—C1A—C6A99.5 (2)C11B—C1B—C6B99.8 (2)
C2A—C1A—C10A113.5 (2)C2B—C1B—C10B112.7 (2)
C11A—C1A—C10A100.6 (2)C11B—C1B—C10B100.4 (2)
C6A—C1A—C10A110.6 (2)C6B—C1B—C10B110.9 (2)
O1A—C2A—C3A107.5 (2)O1B—C2B—C3B108.5 (2)
O1A—C2A—C1A112.0 (2)O1B—C2B—C1B111.2 (2)
C3A—C2A—C1A110.6 (2)C3B—C2B—C1B109.3 (2)
O1A—C2A—H2A108.9O1B—C2B—H2B109.3
C3A—C2A—H2A108.9C3B—C2B—H2B109.3
C1A—C2A—H2A108.9C1B—C2B—H2B109.3
C2A—C3A—C4A112.2 (2)C2B—C3B—C4B112.2 (2)
C2A—C3A—H3A1109.2C2B—C3B—H3B1109.2
C4A—C3A—H3A1109.2C4B—C3B—H3B1109.2
C2A—C3A—H3A2109.2C2B—C3B—H3B2109.2
C4A—C3A—H3A2109.2C4B—C3B—H3B2109.2
H3A1—C3A—H3A2107.9H3B1—C3B—H3B2107.9
C5A—C4A—C3A112.5 (2)C5B—C4B—C3B113.3 (2)
C5A—C4A—H4A1109.1C5B—C4B—H4B1108.9
C3A—C4A—H4A1109.1C3B—C4B—H4B1108.9
C5A—C4A—H4A2109.1C5B—C4B—H4B2108.9
C3A—C4A—H4A2109.1C3B—C4B—H4B2108.9
H4A1—C4A—H4A2107.8H4B1—C4B—H4B2107.7
O2A—C5A—C4A110.5 (2)O2B—C5B—C4B110.2 (2)
O2A—C5A—C6A109.2 (2)O2B—C5B—C6B110.5 (2)
C4A—C5A—C6A109.1 (2)C4B—C5B—C6B110.5 (2)
O2A—C5A—H5A109.3O2B—C5B—H5B108.5
C4A—C5A—H5A109.3C4B—C5B—H5B108.5
C6A—C5A—H5A109.3C6B—C5B—H5B108.5
O3A—C6A—C5A107.1 (2)O3B—C6B—C5B107.8 (2)
O3A—C6A—C1A106.38 (19)O3B—C6B—C1B104.52 (19)
C5A—C6A—C1A110.3 (2)C5B—C6B—C1B110.6 (2)
O3A—C6A—C7A110.3 (2)O3B—C6B—C7B111.3 (2)
C5A—C6A—C7A119.3 (2)C5B—C6B—C7B119.3 (2)
C1A—C6A—C7A102.8 (2)C1B—C6B—C7B102.3 (2)
C12A—C7A—C13A107.7 (3)C13B—C7B—C12B107.1 (2)
C12A—C7A—C8A109.1 (2)C13B—C7B—C8B112.7 (3)
C13A—C7A—C8A112.7 (2)C12B—C7B—C8B109.6 (2)
C12A—C7A—C6A112.0 (2)C13B—C7B—C6B113.8 (2)
C13A—C7A—C6A114.0 (2)C12B—C7B—C6B111.8 (2)
C8A—C7A—C6A101.2 (2)C8B—C7B—C6B101.9 (2)
C9A—C8A—C11A99.9 (2)C9B—C8B—C11B99.7 (2)
C9A—C8A—C7A110.9 (2)C9B—C8B—C7B111.5 (3)
C11A—C8A—C7A103.7 (2)C11B—C8B—C7B103.2 (2)
C9A—C8A—H8A113.7C9B—C8B—H8B113.7
C11A—C8A—H8A113.7C11B—C8B—H8B113.7
C7A—C8A—H8A113.7C7B—C8B—H8B113.7
C8A—C9A—C10A102.2 (2)C8B—C9B—C10B102.1 (2)
C8A—C9A—H9A1111.3C8B—C9B—H9B1111.4
C10A—C9A—H9A1111.3C10B—C9B—H9B1111.4
C8A—C9A—H9A2111.3C8B—C9B—H9B2111.4
C10A—C9A—H9A2111.3C10B—C9B—H9B2111.4
H9A1—C9A—H9A2109.2H9B1—C9B—H9B2109.2
C9A—C10A—C1A104.1 (2)C9B—C10B—C1B104.2 (2)
C9A—C10A—H10A110.9C9B—C10B—H10C110.9
C1A—C10A—H10A110.9C1B—C10B—H10C110.9
C9A—C10A—H10B110.9C9B—C10B—H10D110.9
C1A—C10A—H10B110.9C1B—C10B—H10D110.9
H10A—C10A—H10B108.9H10C—C10B—H10D108.9
C8A—C11A—C1A94.4 (2)C8B—C11B—C1B94.4 (2)
C8A—C11A—H11A112.8C8B—C11B—H11C112.8
C1A—C11A—H11A112.8C1B—C11B—H11C112.8
C8A—C11A—H11B112.8C8B—C11B—H11D112.8
C1A—C11A—H11B112.8C1B—C11B—H11D112.8
H11A—C11A—H11B110.3H11C—C11B—H11D110.3
C7A—C12A—H12A109.5C7B—C12B—H12D109.5
C7A—C12A—H12B109.5C7B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C7A—C12A—H12C109.5C7B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C7A—C13A—H13A109.5C7B—C13B—H13D109.5
C7A—C13A—H13B109.5C7B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C7A—C13A—H13C109.5C7B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C2A—O1A—H1A109.5C2B—O1B—H1B109.5
C5A—O2A—H2A1109.5C5B—O2B—H2B1109.5
C6A—O3A—H3A109.5C6B—O3B—H3B109.5
C11A—C1A—C2A—O1A67.4 (3)C10B—C1B—C2B—O1B54.3 (3)
C6A—C1A—C2A—O1A177.2 (2)C11B—C1B—C2B—C3B175.3 (2)
C10A—C1A—C2A—O1A52.6 (3)C6B—C1B—C2B—C3B59.1 (3)
C11A—C1A—C2A—C3A172.7 (2)C10B—C1B—C2B—C3B65.4 (3)
C6A—C1A—C2A—C3A57.3 (3)O1B—C2B—C3B—C4B177.1 (2)
C10A—C1A—C2A—C3A67.3 (3)C1B—C2B—C3B—C4B55.7 (3)
O1A—C2A—C3A—C4A176.8 (2)C2B—C3B—C4B—C5B53.1 (3)
C1A—C2A—C3A—C4A54.3 (3)C3B—C4B—C5B—O2B174.6 (2)
C2A—C3A—C4A—C5A53.9 (3)C3B—C4B—C5B—C6B52.2 (3)
C3A—C4A—C5A—O2A175.2 (2)O2B—C5B—C6B—O3B63.8 (3)
C3A—C4A—C5A—C6A55.2 (3)C4B—C5B—C6B—O3B58.4 (3)
O2A—C5A—C6A—O3A63.7 (3)O2B—C5B—C6B—C1B177.5 (2)
C4A—C5A—C6A—O3A57.2 (3)C4B—C5B—C6B—C1B55.2 (3)
O2A—C5A—C6A—C1A179.1 (2)O2B—C5B—C6B—C7B64.3 (3)
C4A—C5A—C6A—C1A58.2 (3)C4B—C5B—C6B—C7B173.4 (2)
O2A—C5A—C6A—C7A62.4 (3)C2B—C1B—C6B—O3B55.9 (2)
C4A—C5A—C6A—C7A176.8 (2)C11B—C1B—C6B—O3B73.4 (2)
C2A—C1A—C6A—O3A55.6 (3)C10B—C1B—C6B—O3B178.5 (2)
C11A—C1A—C6A—O3A72.9 (2)C2B—C1B—C6B—C5B59.8 (3)
C10A—C1A—C6A—O3A178.2 (2)C11B—C1B—C6B—C5B170.9 (2)
C2A—C1A—C6A—C5A60.1 (3)C10B—C1B—C6B—C5B65.7 (3)
C11A—C1A—C6A—C5A171.3 (2)C2B—C1B—C6B—C7B172.1 (2)
C10A—C1A—C6A—C5A66.0 (3)C11B—C1B—C6B—C7B42.8 (2)
C2A—C1A—C6A—C7A171.6 (2)C10B—C1B—C6B—C7B62.4 (3)
C11A—C1A—C6A—C7A43.0 (2)C5B—C6B—C7B—C13B9.4 (3)
C10A—C1A—C6A—C7A62.2 (3)C1B—C6B—C7B—C13B112.9 (3)
O3A—C6A—C7A—C12A12.1 (3)O3B—C6B—C7B—C12B14.5 (3)
C5A—C6A—C7A—C12A112.4 (3)O3B—C6B—C7B—C13B135.9 (2)
C1A—C6A—C7A—C12A125.2 (2)C5B—C6B—C7B—C12B112.0 (3)
O3A—C6A—C7A—C13A134.7 (3)C1B—C6B—C7B—C12B125.6 (2)
C5A—C6A—C7A—C13A10.2 (4)O3B—C6B—C7B—C8B102.4 (2)
C1A—C6A—C7A—C13A112.2 (3)C5B—C6B—C7B—C8B131.0 (2)
O3A—C6A—C7A—C8A104.1 (2)C1B—C6B—C7B—C8B8.7 (2)
C5A—C6A—C7A—C8A131.4 (2)C13B—C7B—C8B—C9B44.7 (3)
C1A—C6A—C7A—C8A9.0 (2)C12B—C7B—C8B—C9B163.8 (2)
C12A—C7A—C8A—C9A163.7 (3)C6B—C7B—C8B—C9B77.6 (3)
C13A—C7A—C8A—C9A44.1 (3)C13B—C7B—C8B—C11B150.9 (2)
C6A—C7A—C8A—C9A78.0 (3)C12B—C7B—C8B—C11B90.0 (3)
C12A—C7A—C8A—C11A89.9 (3)C6B—C7B—C8B—C11B28.6 (3)
C13A—C7A—C8A—C11A150.5 (3)C11B—C8B—C9B—C10B43.0 (3)
C6A—C7A—C8A—C11A28.3 (3)C7B—C8B—C9B—C10B65.5 (3)
C11A—C8A—C9A—C10A42.4 (3)C8B—C9B—C10B—C1B8.4 (3)
C7A—C8A—C9A—C10A66.5 (3)C2B—C1B—C10B—C9B160.0 (2)
C8A—C9A—C10A—C1A7.9 (3)C11B—C1B—C10B—C9B28.9 (3)
C2A—C1A—C10A—C9A160.5 (2)C6B—C1B—C10B—C9B75.9 (3)
C11A—C1A—C10A—C9A29.2 (3)C9B—C8B—C11B—C1B60.5 (2)
C6A—C1A—C10A—C9A75.3 (3)C7B—C8B—C11B—C1B54.4 (2)
C9A—C8A—C11A—C1A60.0 (2)C2B—C1B—C11B—C8B179.2 (2)
C7A—C8A—C11A—C1A54.5 (2)C6B—C1B—C11B—C8B59.5 (2)
C2A—C1A—C11A—C8A179.9 (2)C10B—C1B—C11B—C8B54.0 (2)
C6A—C1A—C11A—C8A59.3 (2)O1A—C2A—C5A—O2A175.0 (4)
C10A—C1A—C11A—C8A54.0 (2)O1A—C2A—C6A—O3A132.2 (3)
C11B—C1B—C2B—O1B65.0 (3)O1B—C2B—C5B—O2B175.0 (4)
C6B—C1B—C2B—O1B178.8 (2)O1B—C2B—C6B—O3B128.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1B0.821.992.754 (3)154
O3A—H3A···O2A0.822.452.826 (2)109
O3B—H3B···O2B0.822.572.861 (3)103
O2B—H2B1···O1Ai0.822.122.876 (3)154
O2A—H2A1···O2Bii0.822.092.908 (3)177
O3A—H3A···O2Aiii0.821.992.733 (2)151
O1B—H1B···O3Biv0.822.172.971 (3)166
O3B—H3B···O3Aiv0.822.172.940 (2)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z+1; (iii) x+2, y, z+2; (iv) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC13H22O3
Mr226.31
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.812 (2), 11.141 (1), 11.443 (2)
α, β, γ (°)82.47 (1), 77.56 (1), 89.46 (1)
V3)1210.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.5 × 0.4 × 0.3
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4499, 4259, 2972
Rint0.015
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.156, 1.10
No. of reflections4259
No. of parameters299
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.24, 0.21

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), MULTAN88 (Debaerdemaeker et al., 1988), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1995) and WinGX (Farrugia, 1999), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
C1A—C2A1.524 (4)C1B—C2B1.524 (4)
C2A—O1A1.434 (3)C2B—O1B1.433 (3)
C5A—O2A1.436 (3)C5B—O2B1.441 (3)
C6A—O3A1.434 (3)C6B—O3B1.449 (3)
C6A—C7A1.596 (4)C6B—C7B1.589 (4)
C7A—C8A1.561 (4)C7B—C8B1.565 (4)
C2A—C1A—C6A110.0 (2)C2B—C1B—C6B110.2 (2)
C11A—C1A—C6A99.5 (2)C11B—C1B—C6B99.8 (2)
C11A—C1A—C10A100.6 (2)C11B—C1B—C10B100.4 (2)
C1A—C6A—C7A102.8 (2)C1B—C6B—C7B102.3 (2)
C8A—C7A—C6A101.2 (2)C8B—C7B—C6B101.9 (2)
C6A—C1A—C2A—O1A177.2 (2)C6B—C1B—C2B—O1B178.8 (2)
O1A—C2A—C3A—C4A176.8 (2)O1B—C2B—C3B—C4B177.1 (2)
C3A—C4A—C5A—O2A175.2 (2)C3B—C4B—C5B—O2B174.6 (2)
O2A—C5A—C6A—O3A63.7 (3)O2B—C5B—C6B—O3B63.8 (3)
C4A—C5A—C6A—O3A57.2 (3)C4B—C5B—C6B—O3B58.4 (3)
O2A—C5A—C6A—C1A179.1 (2)O2B—C5B—C6B—C1B177.5 (2)
C2A—C1A—C6A—O3A55.6 (3)C2B—C1B—C6B—O3B55.9 (2)
C10A—C1A—C6A—O3A178.2 (2)C10B—C1B—C6B—O3B178.5 (2)
O3A—C6A—C7A—C12A12.1 (3)O3B—C6B—C7B—C12B14.5 (3)
O3A—C6A—C7A—C13A134.7 (3)O3B—C6B—C7B—C13B135.9 (2)
C1A—C6A—C7A—C8A9.0 (2)C1B—C6B—C7B—C8B8.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1B0.821.992.754 (3)154
O3A—H3A···O2A0.822.452.826 (2)109
O3B—H3B···O2B0.822.572.861 (3)103
O2B—H2B1···O1Ai0.822.122.876 (3)154
O2A—H2A1···O2Bii0.822.092.908 (3)177
O3A—H3A···O2Aiii0.821.992.733 (2)151
O1B—H1B···O3Biv0.822.172.971 (3)166
O3B—H3B···O3Aiv0.822.172.940 (2)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z+1; (iii) x+2, y, z+2; (iv) x+2, y+1, z+1.
 

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