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cis-Verbenol (alternative name: 4,6,6-tri­methyl­bi­cyclo­[3.1.1]­hept-3-en-2-ol), C10H16O, forms an orthorhombic P212121 crystal that contains three mol­ecules per asymmetric unit. These three mol­ecules form hydrogen-bonded helices parallel to the shortest axis of the lattice. The O...O distances associated with the hydrogen bonds are 2.760 (3), 2.760 (3) and 2.766 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827019901570X/bk1491sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827019901570X/bk1491Isup2.hkl
Contains datablock I

CCDC reference: 144629

Comment top

Verbenol is a monoterpene alcohol with four known stereoisomers (Dictionary of Natural Products, 1994). Two enantiomers, (1R,2S,5R) and (1S,2R,5S), are oils and are diastereoisomers of the two solid enantiomeric structures, (1R,2R,5R) and (1S,2S,5S), of which the latter, (I), is studied here. Recent solid-state NMR studies have demonstrated that verbenol exhibits multiple resonances per carbon position in the molecular structure, suggesting polymorphism or multiple molecules per asymmetric unit (Harper & Grant, 1999). An X-ray analysis was performed on (I) to clarify these structural variations and to characterize the associated hydrogen-bonding features. \scheme

The arrangement of the three molecules of the asymmetric unit for (I) is shown in Fig. 1. The crystal of (I) consists of helical hydrogen-bonded chains lying parallel to the shortest axis. The three distinct molecules per asymmetric unit differ primarily in the conformations of the hydrogen-bonded region of verbenol, with C3—C4—O—H dihedral angles of 55, 69 and 74°. All other differences in heavy atom angles, both dihedral and geminal, and in bond lengths were modest between the three unique verbenol molecules, with respective variations of less than 2° and 0.013 Å. Four asymmetric units compose the unit cell arrangement shown in Fig. 2.

Monofunctional alcohols frequently form chains, rings and helices. Such arrangements often contain more than one molecule per asymmetric unit (Brock & Duncan, 1994). The present X-ray structure of verbenol corresponds to a previously described sterol monoalcohol structure (Brock et al., 1994) in the number of molecules per asymmetric unit, general hydrogen-bonding arrangement and space group. Similar hydrogen-bonded helices containing three molecules per asymmetric unit have also been observed in other monoalcohols (Singelenberg & van Eijck, 1987; Zavodnik & Bel'skii, 1987; Escobar & Wittke, 1984), although with different space groups. Solid state NMR analyses demonstrate that other preparations of solid verbenol powder samples contain a second minor polymorph with four molecules per asymmetric unit (Harper & Grant, 1999). A single-crystal of this second structure could not be isolated and hence has not been subjected to X-ray analysis.

Experimental top

Verbenol was obtained from Aldrich as a 50+% enantiomeric excess (1S,2S,5S/1R,2R,5R) mixture and used as received. Reported enantiomeric excess was determined by Aldrich using chiral stationary phase gas chromatography. A 0.6/0.4 (e.s.d. 0.1) 1S,2S,5S/1R,2R,5R enantiomeric ratio was determined in our lab by polarimetry on a sample dissolved in acetone. The enantiomeric content is a measure of the bulk material and a corresponding value for the individual crystal could not be determined with the methods used. A verbenol purity of 94% was found by gas chromatography on an achiral stationary phase. Crystals of (I) (m.p. 341.5–346.5 K) were prepared by slow evaporation of a solution in 100% methanol.

Refinement top

Hydroxy H atoms were located and refined isotropically. All other H atoms were refined as riding models on the appropriate C atoms using the SHELXL97 (Sheldrick, 1997) restraints and assigned isotropic displacement parameters of 1.5 for methyl H and 1.2 for all others.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1998) and ORTEP-3 for Windows (Farrugia 1997); software used to prepare material for publication: ORTEP-3 for Windows.

Figures top
[Figure 1] Fig. 1. Arrangement of the three (+)-1S,2S,5S-cis-verbenol molecules in the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii. Please check and confirm atom labels.
[Figure 2] Fig. 2. Arrangement of verbenol in the unit cell of (I) viewed along the a axis. Extension of the helical structure illustrates the propagation of the coil beyond a given asymmetric unit.
(I) top
Crystal data top
C10H16ODx = 1.089 Mg m3
Mr = 152.23Melting point: 341.5-346.5 K K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 7.0115 (1) ÅCell parameters from 252 reflections
b = 18.7691 (6) Åθ = 4.1–25.0°
c = 21.1681 (7) ŵ = 0.07 mm1
V = 2785.71 (13) Å3T = 200 K
Z = 12Prism, colorless
F(000) = 10080.20 × 0.14 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.042
ϕ + ω scanθmax = 24.8°, θmin = 4.1°
13724 measured reflectionsh = 87
2717 independent reflectionsk = 2222
2360 reflections with I > 2σ(I)l = 2424
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047Calculated w = 1/[σ2(Fo2) + (0.0812P)2 + 0.6806P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.24 e Å3
2717 reflectionsΔρmin = 0.23 e Å3
310 parameters
Crystal data top
C10H16OV = 2785.71 (13) Å3
Mr = 152.23Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 7.0115 (1) ŵ = 0.07 mm1
b = 18.7691 (6) ÅT = 200 K
c = 21.1681 (7) Å0.20 × 0.14 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
2360 reflections with I > 2σ(I)
13724 measured reflectionsRint = 0.042
2717 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.24 e Å3
2717 reflectionsΔρmin = 0.23 e Å3
310 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9297 (3)0.13325 (11)0.69441 (12)0.0461 (6)
HO10.841 (6)0.161 (2)0.6964 (19)0.062 (12)*
C11.0130 (4)0.04798 (15)0.61378 (14)0.0365 (7)
H11.06190.08890.58820.044*
C20.8642 (4)0.00134 (16)0.58270 (14)0.0391 (7)
C30.7918 (4)0.05117 (17)0.61743 (15)0.0406 (7)
H30.69780.08190.60010.049*
C40.8597 (4)0.06179 (15)0.68452 (15)0.0392 (7)
H40.74970.05350.71370.047*
C51.0155 (4)0.00809 (15)0.70005 (14)0.0373 (7)
H51.06870.01130.74380.045*
C61.1669 (4)0.00033 (15)0.64610 (14)0.0370 (7)
C70.9383 (5)0.06603 (16)0.68093 (15)0.0421 (7)
H7A0.7980.07080.68390.051*
H7B1.00410.10650.70150.051*
C80.8104 (6)0.0148 (2)0.51534 (16)0.0590 (10)
H8A0.88050.05630.49950.089*
H8B0.84250.02710.48980.089*
H8C0.6730.02390.51260.089*
C91.2399 (5)0.06494 (17)0.61060 (17)0.0447 (8)
H9A1.13160.09350.59590.067*
H9B1.31550.04930.57420.067*
H9C1.31970.09380.63870.067*
C101.3407 (5)0.04280 (19)0.66881 (18)0.0538 (9)
H10A1.2970.0850.69190.081*
H10B1.4190.01320.69670.081*
H10C1.41660.05770.63230.081*
O1'0.5930 (3)0.20817 (12)0.68225 (12)0.0439 (6)
HO1'0.530 (7)0.200 (2)0.707 (2)0.068 (16)*
C1'0.6466 (5)0.38039 (16)0.58602 (15)0.0467 (8)
H1'0.68710.42740.56840.056*
C2'0.4952 (5)0.38247 (17)0.63741 (15)0.0462 (8)
C3'0.4337 (5)0.32051 (17)0.65885 (15)0.0422 (7)
H3'0.33810.31890.69060.051*
C4'0.5152 (5)0.25252 (16)0.63289 (15)0.0398 (7)
H4'0.41070.22560.61130.048*
C5'0.6702 (5)0.26843 (15)0.58467 (14)0.0390 (7)
H5'0.73210.22580.56510.047*
C6'0.8094 (5)0.32900 (17)0.60630 (15)0.0427 (8)
C7'0.5842 (6)0.32335 (17)0.53745 (14)0.0478 (8)
H7'10.65150.32610.49640.057*
H7'20.44450.31940.53170.057*
C8'0.4249 (8)0.45320 (19)0.66133 (19)0.0738 (13)
H8'10.48910.49170.63840.111*
H8'20.45280.45730.70650.111*
H8'30.28690.45670.65460.111*
C9'0.8807 (5)0.33147 (19)0.67444 (16)0.0524 (9)
H9'10.98010.29540.68040.079*
H9'20.77440.32190.70330.079*
H9'30.93340.37880.68340.079*
C10'0.9832 (6)0.3339 (2)0.56249 (19)0.0629 (10)
H10D0.94080.33250.51840.094*
H10E1.06890.29370.57070.094*
H10F1.0510.37870.57040.094*
O1''0.2623 (3)0.18282 (14)0.74930 (11)0.0459 (6)
HO1''0.180 (7)0.167 (2)0.731 (2)0.059 (13)*
C1''0.3540 (5)0.20439 (17)0.92741 (15)0.0447 (8)
H1''0.40540.20240.97140.054*
C2''0.2085 (5)0.14812 (17)0.90990 (15)0.0415 (7)
C3''0.1318 (5)0.15230 (17)0.85232 (16)0.0423 (8)
H3''0.03920.11850.83910.051*
C4''0.1939 (4)0.21129 (16)0.80842 (15)0.0411 (7)
H4''0.08090.24220.79950.049*
C5''0.3461 (5)0.25668 (15)0.83877 (15)0.0405 (7)
H5''0.39410.29720.81250.049*
C6''0.5040 (4)0.21154 (17)0.87321 (15)0.0386 (7)
C7''0.2725 (5)0.27704 (18)0.90547 (17)0.0516 (9)
H7''10.33660.3190.92430.062*
H7''20.1320.28090.90870.062*
C8''0.1587 (6)0.0908 (2)0.95609 (18)0.0659 (11)
H8''10.23140.09780.99510.099*
H8''20.19010.04420.93790.099*
H8''30.02190.09280.96550.099*
C9''0.5812 (5)0.14423 (16)0.84258 (17)0.0422 (7)
H9''10.47470.11390.82930.063*
H9''20.66060.11840.8730.063*
H9''30.65820.1570.80560.063*
C10''0.6759 (5)0.2577 (2)0.8924 (2)0.0587 (10)
H10G0.63050.30170.91230.088*
H10H0.7510.26950.85480.088*
H10I0.75570.23130.92240.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0368 (12)0.0359 (11)0.0656 (15)0.0028 (10)0.0063 (11)0.0101 (11)
C10.0377 (16)0.0336 (14)0.0383 (16)0.0034 (13)0.0008 (13)0.0003 (13)
C20.0328 (15)0.0436 (16)0.0410 (16)0.0082 (14)0.0050 (13)0.0034 (14)
C30.0282 (14)0.0443 (17)0.0493 (18)0.0006 (13)0.0087 (13)0.0042 (15)
C40.0318 (15)0.0403 (15)0.0455 (17)0.0030 (13)0.0007 (14)0.0042 (14)
C50.0396 (16)0.0392 (15)0.0333 (15)0.0007 (13)0.0022 (13)0.0027 (12)
C60.0307 (14)0.0358 (15)0.0447 (17)0.0025 (13)0.0018 (13)0.0012 (13)
C70.0475 (18)0.0381 (16)0.0408 (17)0.0031 (14)0.0010 (16)0.0049 (14)
C80.059 (2)0.071 (2)0.047 (2)0.006 (2)0.0155 (17)0.0008 (18)
C90.0332 (16)0.0446 (17)0.056 (2)0.0061 (14)0.0004 (15)0.0046 (15)
C100.0433 (19)0.0534 (19)0.064 (2)0.0101 (17)0.0126 (17)0.0005 (17)
O1'0.0389 (12)0.0440 (12)0.0489 (14)0.0083 (10)0.0076 (11)0.0147 (11)
C1'0.062 (2)0.0352 (15)0.0431 (17)0.0099 (16)0.0064 (17)0.0067 (14)
C2'0.060 (2)0.0392 (16)0.0392 (17)0.0105 (16)0.0045 (16)0.0030 (14)
C3'0.0383 (17)0.0460 (18)0.0423 (16)0.0091 (15)0.0011 (14)0.0062 (14)
C4'0.0374 (16)0.0361 (15)0.0458 (17)0.0029 (14)0.0002 (14)0.0057 (13)
C5'0.0440 (17)0.0390 (16)0.0340 (15)0.0026 (14)0.0029 (14)0.0040 (13)
C6'0.0432 (18)0.0440 (17)0.0409 (17)0.0072 (15)0.0000 (14)0.0001 (14)
C7'0.058 (2)0.0517 (18)0.0338 (16)0.0019 (17)0.0062 (15)0.0019 (14)
C8'0.111 (4)0.049 (2)0.061 (2)0.026 (2)0.001 (3)0.0006 (18)
C9'0.048 (2)0.058 (2)0.051 (2)0.0095 (17)0.0081 (17)0.0034 (17)
C10'0.053 (2)0.076 (3)0.060 (2)0.014 (2)0.0110 (19)0.006 (2)
O1''0.0361 (12)0.0638 (15)0.0378 (12)0.0074 (11)0.0006 (10)0.0047 (11)
C1''0.0406 (17)0.0554 (18)0.0381 (16)0.0014 (15)0.0001 (15)0.0077 (15)
C2''0.0341 (16)0.0507 (18)0.0396 (17)0.0001 (14)0.0062 (14)0.0017 (14)
C3''0.0300 (16)0.0479 (18)0.0490 (19)0.0032 (14)0.0067 (15)0.0033 (15)
C4''0.0322 (15)0.0464 (16)0.0446 (17)0.0050 (13)0.0014 (13)0.0013 (14)
C5''0.0390 (16)0.0322 (14)0.0502 (18)0.0038 (13)0.0007 (15)0.0008 (13)
C6''0.0294 (15)0.0423 (16)0.0443 (17)0.0015 (13)0.0029 (13)0.0041 (14)
C7''0.0465 (19)0.0478 (18)0.060 (2)0.0071 (15)0.0025 (17)0.0163 (16)
C8''0.064 (3)0.077 (3)0.056 (2)0.008 (2)0.015 (2)0.0103 (19)
C9''0.0336 (16)0.0420 (16)0.0508 (18)0.0042 (13)0.0004 (15)0.0017 (14)
C10''0.0431 (19)0.060 (2)0.073 (3)0.0106 (18)0.0092 (18)0.0115 (19)
Geometric parameters (Å, º) top
O1—C41.444 (3)C5'—H5'1
O1—HO10.81 (4)C6'—C9'1.527 (5)
C1—C21.512 (4)C6'—C10'1.534 (5)
C1—C71.552 (4)C7'—H7'10.99
C1—C61.567 (4)C7'—H7'20.99
C1—H11C8'—H8'10.98
C2—C31.330 (4)C8'—H8'20.98
C2—C81.496 (4)C8'—H8'30.98
C3—C41.511 (4)C9'—H9'10.98
C3—H30.95C9'—H9'20.98
C4—C51.522 (4)C9'—H9'30.98
C4—H41C10'—H10D0.98
C5—C71.547 (4)C10'—H10E0.98
C5—C61.566 (4)C10'—H10F0.98
C5—H51O1''—C4''1.443 (4)
C6—C91.516 (4)O1''—HO1''0.75 (5)
C6—C101.540 (4)C1''—C2''1.515 (4)
C7—H7A0.99C1''—C7''1.550 (5)
C7—H7B0.99C1''—C6''1.562 (4)
C8—H8A0.98C1''—H1''1
C8—H8B0.98C2''—C3''1.334 (5)
C8—H8C0.98C2''—C8''1.496 (5)
C9—H9A0.98C3''—C4''1.509 (4)
C9—H9B0.98C3''—H3''0.95
C9—H9C0.98C4''—C5''1.509 (4)
C10—H10A0.98C4''—H4''1
C10—H10B0.98C5''—C7''1.551 (5)
C10—H10C0.98C5''—C6''1.573 (4)
O1'—C4'1.443 (4)C5''—H5''1
O1'—HO1'0.70 (4)C6''—C9''1.520 (4)
C1'—C2'1.521 (5)C6''—C10''1.539 (4)
C1'—C7'1.547 (4)C7''—H7''10.99
C1'—C6'1.555 (5)C7''—H7''20.99
C1'—H1'1C8''—H8''10.98
C2'—C3'1.321 (5)C8''—H8''20.98
C2'—C8'1.504 (5)C8''—H8''30.98
C3'—C4'1.503 (4)C9''—H9''10.98
C3'—H3'0.95C9''—H9''20.98
C4'—C5'1.521 (4)C9''—H9''30.98
C4'—H4'1C10''—H10G0.98
C5'—C7'1.557 (4)C10''—H10H0.98
C5'—C6'1.567 (4)C10''—H10I0.98
C4—O1—HO1110 (3)C9'—C6'—C5'120.1 (3)
C2—C1—C7107.0 (3)C10'—C6'—C5'111.2 (3)
C2—C1—C6109.3 (2)C1'—C6'—C5'85.0 (2)
C7—C1—C687.6 (2)C1'—C7'—C5'85.5 (2)
C2—C1—H1116.4C1'—C7'—H7'1114.4
C7—C1—H1116.4C5'—C7'—H7'1114.4
C6—C1—H1116.4C1'—C7'—H7'2114.4
C3—C2—C8123.7 (3)C5'—C7'—H7'2114.4
C3—C2—C1116.8 (3)H7'1—C7'—H7'2111.5
C8—C2—C1119.4 (3)C2'—C8'—H8'1109.5
C2—C3—C4119.8 (3)C2'—C8'—H8'2109.5
C2—C3—H3120.1H8'1—C8'—H8'2109.5
C4—C3—H3120.1C2'—C8'—H8'3109.5
O1—C4—C3111.5 (3)H8'1—C8'—H8'3109.5
O1—C4—C5109.9 (2)H8'2—C8'—H8'3109.5
C3—C4—C5110.0 (2)C6'—C9'—H9'1109.5
O1—C4—H4108.5C6'—C9'—H9'2109.5
C3—C4—H4108.5H9'1—C9'—H9'2109.5
C5—C4—H4108.5C6'—C9'—H9'3109.5
C4—C5—C7106.7 (2)H9'1—C9'—H9'3109.5
C4—C5—C6113.0 (2)H9'2—C9'—H9'3109.5
C7—C5—C687.9 (2)C6'—C10'—H10D109.5
C4—C5—H5115.3C6'—C10'—H10E109.5
C7—C5—H5115.3H10D—C10'—H10E109.5
C6—C5—H5115.3C6'—C10'—H10F109.5
C9—C6—C10108.0 (3)H10D—C10'—H10F109.5
C9—C6—C5121.1 (3)H10E—C10'—H10F109.5
C10—C6—C5111.0 (2)C4''—O1''—HO1''109 (3)
C9—C6—C1118.6 (3)C2''—C1''—C7''107.0 (3)
C10—C6—C1112.2 (2)C2''—C1''—C6''109.5 (2)
C5—C6—C184.6 (2)C7''—C1''—C6''87.3 (2)
C5—C7—C185.7 (2)C2''—C1''—H1''116.4
C5—C7—H7A114.4C7''—C1''—H1''116.4
C1—C7—H7A114.4C6''—C1''—H1''116.4
C5—C7—H7B114.4C3''—C2''—C8''123.1 (3)
C1—C7—H7B114.4C3''—C2''—C1''117.0 (3)
H7A—C7—H7B111.5C8''—C2''—C1''119.9 (3)
C2—C8—H8A109.5C2''—C3''—C4''119.3 (3)
C2—C8—H8B109.5C2''—C3''—H3''120.3
H8A—C8—H8B109.5C4''—C3''—H3''120.3
C2—C8—H8C109.5O1''—C4''—C5''110.1 (3)
H8A—C8—H8C109.5O1''—C4''—C3''111.0 (3)
H8B—C8—H8C109.5C5''—C4''—C3''110.8 (3)
C6—C9—H9A109.5O1''—C4''—H4''108.3
C6—C9—H9B109.5C5''—C4''—H4''108.3
H9A—C9—H9B109.5C3''—C4''—H4''108.3
C6—C9—H9C109.5C4''—C5''—C7''106.9 (3)
H9A—C9—H9C109.5C4''—C5''—C6''113.0 (2)
H9B—C9—H9C109.5C7''—C5''—C6''86.8 (2)
C6—C10—H10A109.5C4''—C5''—H5''115.5
C6—C10—H10B109.5C7''—C5''—H5''115.5
H10A—C10—H10B109.5C6''—C5''—H5''115.5
C6—C10—H10C109.5C9''—C6''—C10''107.6 (3)
H10A—C10—H10C109.5C9''—C6''—C1''118.8 (3)
H10B—C10—H10C109.5C10''—C6''—C1''112.4 (3)
C4'—O1'—HO1'115 (4)C9''—C6''—C5''120.0 (3)
C2'—C1'—C7'107.2 (3)C10''—C6''—C5''111.7 (3)
C2'—C1'—C6'109.3 (2)C1''—C6''—C5''85.0 (2)
C7'—C1'—C6'87.8 (2)C1''—C7''—C5''86.2 (2)
C2'—C1'—H1'116.3C1''—C7''—H7''1114.3
C7'—C1'—H1'116.3C5''—C7''—H7''1114.3
C6'—C1'—H1'116.3C1''—C7''—H7''2114.3
C3'—C2'—C8'123.7 (3)C5''—C7''—H7''2114.3
C3'—C2'—C1'116.8 (3)H7''1—C7''—H7''2111.4
C8'—C2'—C1'119.5 (3)C2''—C8''—H8''1109.5
C2'—C3'—C4'119.9 (3)C2''—C8''—H8''2109.5
C2'—C3'—H3'120.1H8''1—C8''—H8''2109.5
C4'—C3'—H3'120.1C2''—C8''—H8''3109.5
O1'—C4'—C3'111.7 (3)H8''1—C8''—H8''3109.5
O1'—C4'—C5'109.2 (3)H8''2—C8''—H8''3109.5
C3'—C4'—C5'110.5 (2)C6''—C9''—H9''1109.5
O1'—C4'—H4'108.4C6''—C9''—H9''2109.5
C3'—C4'—H4'108.4H9''1—C9''—H9''2109.5
C5'—C4'—H4'108.4C6''—C9''—H9''3109.5
C4'—C5'—C7'106.5 (3)H9''1—C9''—H9''3109.5
C4'—C5'—C6'113.0 (2)H9''2—C9''—H9''3109.5
C7'—C5'—C6'87.0 (2)C6''—C10''—H10G109.5
C4'—C5'—H5'115.6C6''—C10''—H10H109.5
C7'—C5'—H5'115.6H10G—C10''—H10H109.5
C6'—C5'—H5'115.6C6''—C10''—H10I109.5
C9'—C6'—C10'108.0 (3)H10G—C10''—H10I109.5
C9'—C6'—C1'118.8 (3)H10H—C10''—H10I109.5
C10'—C6'—C1'112.3 (3)
C7—C1—C2—C344.9 (3)C2'—C1'—C6'—C10'170.1 (3)
C6—C1—C2—C348.6 (3)C7'—C1'—C6'—C10'82.5 (3)
C7—C1—C2—C8136.8 (3)C2'—C1'—C6'—C5'79.1 (3)
C6—C1—C2—C8129.7 (3)C7'—C1'—C6'—C5'28.4 (2)
C8—C2—C3—C4178.1 (3)C4'—C5'—C6'—C9'42.1 (4)
C1—C2—C3—C40.1 (4)C7'—C5'—C6'—C9'148.8 (3)
C2—C3—C4—O1124.5 (3)C4'—C5'—C6'—C10'169.6 (3)
C2—C3—C4—C52.4 (4)C7'—C5'—C6'—C10'83.7 (3)
O1—C4—C5—C7173.5 (2)C4'—C5'—C6'—C1'78.5 (3)
C3—C4—C5—C750.5 (3)C7'—C5'—C6'—C1'28.2 (2)
O1—C4—C5—C678.6 (3)C2'—C1'—C7'—C5'81.0 (3)
C3—C4—C5—C644.4 (3)C6'—C1'—C7'—C5'28.6 (2)
C4—C5—C6—C940.9 (4)C4'—C5'—C7'—C1'84.8 (3)
C7—C5—C6—C9148.2 (3)C6'—C5'—C7'—C1'28.3 (2)
C4—C5—C6—C10168.9 (2)C7''—C1''—C2''—C3''44.7 (4)
C7—C5—C6—C1083.8 (3)C6''—C1''—C2''—C3''48.5 (4)
C4—C5—C6—C179.4 (3)C7''—C1''—C2''—C8''136.1 (3)
C7—C5—C6—C127.9 (2)C6''—C1''—C2''—C8''130.7 (3)
C2—C1—C6—C943.2 (3)C8''—C2''—C3''—C4''178.8 (3)
C7—C1—C6—C9150.4 (3)C1''—C2''—C3''—C4''0.4 (4)
C2—C1—C6—C10170.2 (3)C2''—C3''—C4''—O1''124.5 (3)
C7—C1—C6—C1082.7 (3)C2''—C3''—C4''—C5''1.9 (4)
C2—C1—C6—C579.4 (3)O1''—C4''—C5''—C7''172.8 (2)
C7—C1—C6—C527.8 (2)C3''—C4''—C5''—C7''49.6 (3)
C4—C5—C7—C185.3 (3)O1''—C4''—C5''—C6''79.0 (3)
C6—C5—C7—C128.1 (2)C3''—C4''—C5''—C6''44.2 (3)
C2—C1—C7—C581.3 (2)C2''—C1''—C6''—C9''42.9 (4)
C6—C1—C7—C528.1 (2)C7''—C1''—C6''—C9''150.0 (3)
C7'—C1'—C2'—C3'44.7 (4)C2''—C1''—C6''—C10''169.8 (3)
C6'—C1'—C2'—C3'49.1 (4)C7''—C1''—C6''—C10''83.2 (3)
C7'—C1'—C2'—C8'135.8 (3)C2''—C1''—C6''—C5''78.8 (3)
C6'—C1'—C2'—C8'130.4 (3)C7''—C1''—C6''—C5''28.3 (2)
C8'—C2'—C3'—C4'178.8 (3)C4''—C5''—C6''—C9''41.7 (4)
C1'—C2'—C3'—C4'0.7 (5)C7''—C5''—C6''—C9''148.8 (3)
C2'—C3'—C4'—O1'123.9 (3)C4''—C5''—C6''—C10''169.0 (3)
C2'—C3'—C4'—C5'2.1 (4)C7''—C5''—C6''—C10''83.9 (3)
O1'—C4'—C5'—C7'173.4 (2)C4''—C5''—C6''—C1''78.8 (3)
C3'—C4'—C5'—C7'50.2 (3)C7''—C5''—C6''—C1''28.3 (2)
O1'—C4'—C5'—C6'79.6 (3)C2''—C1''—C7''—C5''80.9 (3)
C3'—C4'—C5'—C6'43.7 (3)C6''—C1''—C7''—C5''28.7 (2)
C2'—C1'—C6'—C9'42.7 (4)C4''—C5''—C7''—C1''84.7 (3)
C7'—C1'—C6'—C9'150.2 (3)C6''—C5''—C7''—C1''28.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···O10.81 (4)1.97 (4)2.760 (3)162 (4)
O1—HO1···O10.70 (4)2.11 (5)2.760 (3)156 (5)
O1—HO1···O1i0.75 (5)2.02 (5)2.766 (3)170 (4)
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC10H16O
Mr152.23
Crystal system, space groupOrthorhombic, P212121
Temperature (K)200
a, b, c (Å)7.0115 (1), 18.7691 (6), 21.1681 (7)
V3)2785.71 (13)
Z12
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.20 × 0.14 × 0.13
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13724, 2717, 2360
Rint0.042
(sin θ/λ)max1)0.590
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.05
No. of reflections2717
No. of parameters310
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.23

Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SIR97 (Altomare et al., 1997), SHELXL97 (Sheldrick, 1997), WinGX (Farrugia, 1998) and ORTEP-3 for Windows (Farrugia 1997), ORTEP-3 for Windows.

Selected geometric parameters (Å, º) top
O1—C41.444 (3)O1''—C4''1.443 (4)
O1'—C4'1.443 (4)
O1—C4—C3111.5 (3)O1''—C4''—C3''111.0 (3)
O1'—C4'—C3'111.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···O1'0.81 (4)1.97 (4)2.760 (3)162 (4)
O1'—HO1'···O1''0.70 (4)2.11 (5)2.760 (3)156 (5)
O1''—HO1''···O1i0.75 (5)2.02 (5)2.766 (3)170 (4)
Symmetry code: (i) x1, y, z.
 

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