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The stereochemistry of the title compound, C15H26O3, has been established. The compound crystallizes with three molecules in the asymmetric unit and significant variations in the bond distances and angles are reported. Intermolecular hydrogen bonds are observed between the hydroxyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101457X/cf6073sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680101457X/cf6073Isup2.hkl
Contains datablock I

CCDC reference: 175354

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.090
  • Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
EXPT_002 Alert A _exptl_crystal_density_meas is missing, although a method has been given. Density measured experimentally (Mg m-3). The following tests will not be performed. DENSX_01 CELLV_02 Alert A The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 8 Calculated cell volume su = 26.91 Cell volume su given = 3.00
Amber Alert Alert Level B:
DENSM_01 Alert B _exptl_crystal_density_method is given but no value of _exptl_crystal_density_meas is reported. PLAT_707 Alert B D...A Calc 3.007(4), Rep 3.018(3), Dev. 2.75 Sigma O56 -O56 1.555 2.674
Yellow Alert Alert Level C:
CRYSC_01 Alert C The word below has not been recognised as a standard identifier. incolore CRYSC_01 Alert C No recognised colour has been given for crystal colour. PLAT_726 Alert C H...A Calc 2.05171, Rep 2.062(2), Dev. 0.01 Ang. H56 -O56 1.555 2.674 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.34 From the CIF: _reflns_number_total 3985 Count of symmetry unique reflns 4186 Completeness (_total/calc) 95.20% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
2 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

Ce travail fait suite à celui publié dans ce même volume (El Jamili et al., 2001) et concerne l'étude structurale des produits obtenus par oxydation du β-himachalène avec le permanganate de potassium. Ainsi, l'action d'un excès de permanganate de potassium KMnO4, finement broyé, sur le β-himachalène dans un mélange d'acétone–eau (9/1) à une température de 263 K conduit régiosélectivement avec un rendement de 30% au composé étudié. Malgré des études RMN à haute résolution mono et bidimensionnelle, nous n'avons pas pu déduire sa structure. Toutefois, une étude aux rayons X d'un monocristal de ce composé nous a permis, sur la base de la connaissance de la structure absolue du fragment himachalène (Joseph & Dev, 1968; Chiaroni et al., 1991), de lui attribuer la structure (1S,2S,3R,6S,7R)-3,6-époxyhimachalane-2,7-diol, (I) (Fig. 1).

Sa formation provient certainement du réarrangement de l'himachal-2,3,6,7 - tétraol. La maille hexagonale contient trois molécules indépendantes qui sont parfaitement superposables, aux erreurs expérimentales près (Fig. 2). Cependant, les distances et angles de liaison entre atomes de carbone montrent des variations importantes et significatives par rapport aux erreurs expérimentales (Table 1). Ainsi, la distance C—C varie entre 1.506 (4) e t 1.566 (3) Å, et l'angle C—C—C varie entre 100.8 (2) e t 121.5 (2)°. Il est intéressant de remarquer que les distances les plus courtes se retrouvent sur les trois molécules. Ainsi, la distance C3—C17 (ou C23—C37, ou C43—C57) est égale à 1.506 (4) Å dans les trois molécules indépendantes. De même, les deux distances C—C les plus longues C1—C6 et C1—C11 varient entre 1.558 (3) e t 1.561 (3) Å e t 1.559 (3) e t 1.566 (3) Å, respectivement, sur les trois molécules. On notera que ces deux distances les plus longues correspondent à l'angle C—C—C le plus ouvert: de 120.8 (2) à 121.5 (2)°. Le fragment C1—C7—C8—C10—C11, ou son équivalent dans les deux autres molécules, est plan et les atomes C6 et C9 sont situés de part et d'autre de ce plan: entre -0.742 (3) e t -0.749 (3) Å pour C6 et 0.796 (4) e t 0.809 (3) Å pour C9. Le pont oxo C3—O18—C6 divize le cycle à six chaînons en deux fragments plans: C6—C1—C2—C3 et C3—C4—C5—C6. Les angles dièdres entre ces trois plans sont remarquablement constants dans les trois molécules: (i) angle C3—O18—C6 et C3—C4—C5—C6: 124.1 (3)° [124.0 (3), 123.9 (3)°]; (ii) angle C3—O18—C6 et C6—C1—C2—C3: 57.7 (3)° [57.6 (2), 57.2 (3)°]; (iii) angle C3—C4—C5—C6 et C6—C1—C2—C3: 66.5 (2)° [66.5 (2), 66.8 (3)°]. Par ailleurs, l'atome O18 (ou 038, ou O58) est en interaction avec les deux fonctions OH: l'atome O18 est à 2.931 (3) Å de O16 [2.932 (3) e t 2.931 (3) Å pour les deux autre molécules] et à 2.800 (3) Å de O13 [2.775 (3) e t 2.798 (3) Å pour les deux autres molécules] mais l'angle O13—H13···O18 n'est pas favorable à une liaison hydrogène: 111.1 (4)° [114.7 (3) e t 124.7 (3)°]. Par contre, chaque molécule de ce composé établit deux liaisons hydrogène intermoléculaires: O13—H13····O16 et O16—H16····O16 (et leurs correspondants dans les deux autres molécules) dont les distances et les angles sont indiqués dans le Tableau 2.

Experimental top

Dans un réacteur contenant 2 g (9,8 mmol) du β-himachalène solubilisé dans une solution de 30 ml d'un mélange acétone–eau (9/1) e t maintenu sous agitation à une température de 263 K, on ajoute progressivement trois équivalents (29,4 mmol) de permanganate de potassium finement broyé. Après 16 h, la solution est filtrée sur célite puis extraite avec de l'éther. Après avoir évaporé une bonne partie de l'acétone, les phases éthérées sont lavées avec une solution aqueuse d'hydrogénocarbonate de sodium à 15% puis à l'eau, séchées sur sulfate de magnésium et concentrées sous pression réduite. Le résidu obtenu est chromatographié sur colonne de gel de silice avec comme éluant un mélange héxane/acétate d'éthyle (95/5). Rendement 30%; point de fusion 362 K. Les cristaux ont été obtenus par évaporation, à température ambiante, de solutions saturées dans l'héxane.

Refinement top

L'absence d'atomes présentant une diffusion anomale significative ne permet pas de déterminer la configuration absolue de ces molécules. Les réflexions ont donc été moyennées en appliquant la loi de Friedel avant affinement.

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: maXus (Mackay et al., 1999).

Figures top
[Figure 1] Fig. 1. Dessin ORTEPII (Johnson, 1976) du composé (I). Les ellipsoides de vibration des atomes ont une probabilité de 50%.
[Figure 2] Fig. 2. Les trois molécules de l'unité asymétrique. Seuls les atomes d'oxygène ont été numérotés.
(I) top
Crystal data top
C15H26O3Dx = 1.233 Mg m3
Mr = 254.37Mo Kα radiation, λ = 0.71073 Å
Trigonal, P32Cell parameters from 9812 reflections
a = 21.266 (9) Åθ = 2.9–26.3°
c = 7.873 (5) ŵ = 0.08 mm1
V = 3083.5 (3) Å3T = 298 K
Z = 9Prisme, incolore
F(000) = 12600.45 × 0.25 × 0.20 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.052
Radiation source: fine-focus sealed tubeθmax = 26.3°
ϕ scanh = 026
9812 measured reflectionsk = 260
3985 independent reflectionsl = 99
3740 reflections with I > 2σ(I)
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0342P)2 + 1.0542P]
where P = (Fo2 + 2Fc2)/3
3985 reflections(Δ/σ)max = 0.001
485 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C15H26O3Z = 9
Mr = 254.37Mo Kα radiation
Trigonal, P32µ = 0.08 mm1
a = 21.266 (9) ÅT = 298 K
c = 7.873 (5) Å0.45 × 0.25 × 0.20 mm
V = 3083.5 (3) Å3
Data collection top
KappaCCD
diffractometer
3740 reflections with I > 2σ(I)
9812 measured reflectionsRint = 0.052
3985 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.19 e Å3
3985 reflectionsΔρmin = 0.23 e Å3
485 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
xyzUiso*/Ueq
O130.22933 (11)0.49319 (11)0.8310 (2)0.0364 (4)
H130.22630.45430.78620.085 (15)*
O160.33063 (11)0.37593 (10)0.3954 (3)0.0372 (4)
H160.33680.34850.29380.15 (3)*
O180.18260 (10)0.47803 (10)0.5090 (3)0.0285 (4)
O330.17476 (11)0.56695 (11)0.0680 (3)0.0351 (4)
H330.21090.56170.11850.091 (16)*
O360.29161 (10)0.66273 (10)0.5070 (3)0.0339 (4)
H360.32240.67940.60970.065 (12)*
O380.18580 (9)0.51703 (10)0.3860 (3)0.0276 (4)
O530.03739 (11)0.88327 (11)1.1630 (3)0.0357 (4)
H530.00490.88581.09940.073 (14)*
O560.03498 (10)0.99160 (10)0.7245 (3)0.0347 (4)
H560.02431.00850.62170.093 (16)*
O580.02502 (9)0.84137 (10)0.8403 (2)0.0271 (4)
C10.27773 (13)0.50178 (13)0.4851 (4)0.0260 (5)
H10.30600.47040.57960.031*
C20.28211 (14)0.44970 (13)0.3421 (4)0.0292 (5)
H20.29810.46050.23480.035*
C30.20305 (15)0.46710 (14)0.3312 (4)0.0305 (5)
C40.15629 (16)0.54448 (16)0.2568 (4)0.0384 (6)
H4A0.10990.55220.21630.046*
H4B0.18130.55300.16440.046*
C50.14649 (15)0.59334 (15)0.4092 (4)0.0356 (6)
H5A0.16190.62810.38270.043*
H5B0.09650.61910.44760.043*
C60.19671 (13)0.53741 (13)0.5416 (4)0.0259 (5)
C70.18146 (14)0.55600 (14)0.7303 (4)0.0307 (6)
C80.19654 (17)0.61593 (16)0.7865 (4)0.0419 (7)
H8A0.16150.66070.73140.050*
H8B0.18800.62290.90780.050*
C90.27278 (19)0.60367 (19)0.7502 (5)0.0474 (8)
H9A0.30840.55440.78220.057*
H9B0.28090.63640.82070.057*
C100.28487 (19)0.61567 (17)0.5647 (5)0.0446 (7)
H10A0.23930.65410.51960.053*
H10B0.31930.63300.56150.053*
C110.31283 (15)0.54959 (14)0.4446 (4)0.0337 (6)
C120.10279 (16)0.57805 (17)0.7754 (4)0.0422 (7)
H12A0.09760.57880.89660.063*
H12B0.07050.62550.73030.063*
H12C0.09110.54360.72740.063*
C140.39532 (17)0.50003 (19)0.4697 (5)0.0486 (8)
H14A0.40500.48350.58530.073*
H14B0.41280.45900.39510.073*
H14C0.41960.52670.44430.073*
C150.3022 (2)0.57790 (19)0.2623 (5)0.0497 (8)
H15A0.32450.60730.24910.074*
H15B0.32410.53760.18500.074*
H15C0.25120.60660.23830.074*
C170.19022 (19)0.41009 (18)0.2516 (5)0.0464 (8)
H17A0.13980.42440.26150.070*
H17B0.20350.40490.13380.070*
H17C0.21910.36460.30880.070*
C210.16653 (12)0.61507 (13)0.4147 (3)0.0243 (5)
H210.19870.64340.32130.029*
C220.21724 (13)0.61640 (14)0.5574 (4)0.0269 (5)
H220.20700.63250.66520.032*
C230.19646 (14)0.53615 (14)0.5662 (4)0.0292 (5)
C240.11922 (16)0.49183 (16)0.6378 (4)0.0368 (6)
H24A0.11150.51730.73040.044*
H24B0.10960.44470.67770.044*
C250.07117 (15)0.48425 (15)0.4840 (4)0.0353 (6)
H25A0.04440.43450.44370.042*
H25B0.03740.50100.51030.042*
C260.12892 (13)0.53428 (13)0.3553 (3)0.0254 (5)
C270.11028 (14)0.52060 (14)0.1657 (4)0.0304 (6)
C280.05379 (15)0.54081 (17)0.1099 (4)0.0397 (7)
H28A0.04720.53340.01190.048*
H28B0.00800.50700.16300.048*
C290.06943 (17)0.61765 (18)0.1484 (4)0.0419 (7)
H29A0.03840.62810.07770.050*
H29B0.11940.65170.11820.050*
C300.05744 (16)0.62971 (18)0.3344 (4)0.0412 (7)
H30A0.01670.58510.37690.049*
H30B0.04330.66660.33790.049*
C310.12165 (14)0.65268 (15)0.4578 (4)0.0338 (6)
C320.08458 (17)0.44170 (16)0.1176 (4)0.0430 (7)
H32A0.07890.43620.00340.064*
H32B0.03890.41040.17160.064*
H32C0.11980.42900.15450.064*
C340.17431 (18)0.73452 (16)0.4401 (5)0.0452 (7)
H34A0.19100.74550.32480.068*
H34B0.21510.74870.51420.068*
H34C0.14990.76060.47030.068*
C350.09058 (18)0.6398 (2)0.6389 (4)0.0465 (7)
H35A0.12970.65820.71960.070*
H35B0.05920.58870.65710.070*
H35C0.06350.66450.65320.070*
C370.25143 (17)0.52008 (18)0.6451 (4)0.0436 (7)*
H37A0.23410.46890.63860.065*
H37B0.25860.53500.76200.065*
H37C0.29660.54610.58510.065*
C410.09751 (13)0.92800 (13)0.8167 (3)0.0247 (5)
H410.09790.95850.91050.030*
C420.05326 (14)0.93750 (14)0.6736 (4)0.0275 (5)
H420.08020.95080.56620.033*
C430.01377 (14)0.86128 (14)0.6633 (3)0.0296 (5)
C440.00960 (17)0.80838 (16)0.5911 (4)0.0381 (6)
H44A0.03210.76370.55200.046*
H44B0.04360.83030.49790.046*
C450.04582 (16)0.79455 (15)0.7443 (4)0.0343 (6)
H45A0.09490.80560.71800.041*
H45B0.01780.74480.78390.041*
C460.04536 (13)0.84831 (13)0.8742 (4)0.0255 (5)
C470.04673 (15)0.83166 (15)1.0630 (4)0.0315 (6)
C480.11947 (17)0.84032 (18)1.1192 (4)0.0427 (7)
H48A0.11700.83151.24060.051*
H48B0.12510.80261.06430.051*
C490.18710 (17)0.91239 (19)1.0841 (5)0.0468 (8)
H49A0.22600.91631.15560.056*
H49B0.17790.95111.11610.056*
C500.21254 (17)0.92371 (18)0.8994 (5)0.0442 (7)
H50A0.20280.87720.85450.053*
H50B0.26480.95560.89860.053*
C510.17899 (15)0.95560 (15)0.7759 (4)0.0341 (6)
C520.01518 (18)0.75499 (17)1.1076 (4)0.0434 (7)
H52A0.01950.74961.22880.065*
H52B0.00470.71951.06090.065*
H52C0.05990.74801.06100.065*
C540.21837 (17)1.03857 (17)0.7953 (5)0.0474 (8)
H54A0.26751.05900.75620.071*
H54B0.21841.05080.91270.071*
H54C0.19381.05770.72920.071*
C550.19445 (18)0.9406 (2)0.5934 (5)0.0475 (8)
H55A0.17630.96180.51370.071*
H55B0.17080.88910.57490.071*
H55C0.24590.96140.57800.071*
C570.08066 (18)0.85552 (19)0.5828 (4)0.0466 (7)
H57A0.12020.80650.59250.070*
H57B0.07130.86860.46500.070*
H57C0.09310.88780.63950.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O130.0380 (11)0.0358 (11)0.0274 (11)0.0126 (9)0.0052 (8)0.0017 (8)
O160.0362 (10)0.0238 (9)0.0433 (12)0.0088 (8)0.0032 (8)0.0028 (8)
O180.0309 (9)0.0301 (9)0.0269 (10)0.0171 (8)0.0004 (7)0.0029 (7)
O330.0349 (10)0.0394 (11)0.0254 (10)0.0144 (9)0.0031 (7)0.0046 (8)
O360.0227 (9)0.0343 (10)0.0393 (11)0.0101 (8)0.0032 (8)0.0045 (8)
O380.0308 (9)0.0299 (9)0.0252 (9)0.0174 (8)0.0001 (7)0.0003 (7)
O530.0469 (11)0.0407 (11)0.0263 (10)0.0271 (9)0.0032 (8)0.0036 (8)
O560.0405 (11)0.0332 (10)0.0398 (12)0.0254 (9)0.0017 (8)0.0055 (8)
O580.0262 (9)0.0300 (9)0.0260 (10)0.0148 (7)0.0004 (7)0.0011 (7)
C10.0261 (12)0.0231 (12)0.0280 (14)0.0117 (10)0.0019 (9)0.0016 (9)
C20.0343 (14)0.0223 (12)0.0284 (14)0.0121 (11)0.0041 (10)0.0009 (9)
C30.0368 (14)0.0331 (14)0.0232 (13)0.0186 (12)0.0005 (10)0.0047 (10)
C40.0372 (15)0.0398 (15)0.0310 (16)0.0139 (13)0.0102 (11)0.0051 (12)
C50.0311 (14)0.0285 (13)0.0378 (16)0.0077 (11)0.0082 (11)0.0033 (11)
C60.0254 (12)0.0225 (11)0.0273 (14)0.0101 (10)0.0031 (9)0.0004 (9)
C70.0297 (13)0.0263 (13)0.0285 (15)0.0082 (11)0.0015 (10)0.0034 (10)
C80.0446 (17)0.0356 (15)0.0407 (18)0.0165 (13)0.0017 (13)0.0139 (12)
C90.0515 (19)0.0464 (18)0.051 (2)0.0293 (16)0.0031 (14)0.0140 (14)
C100.0496 (18)0.0372 (16)0.057 (2)0.0294 (14)0.0028 (14)0.0031 (13)
C110.0338 (14)0.0313 (14)0.0409 (16)0.0199 (12)0.0021 (11)0.0047 (11)
C120.0308 (15)0.0434 (17)0.0417 (18)0.0106 (13)0.0053 (12)0.0079 (13)
C140.0344 (16)0.0515 (19)0.065 (2)0.0253 (15)0.0008 (14)0.0076 (16)
C150.063 (2)0.0484 (18)0.047 (2)0.0349 (17)0.0002 (15)0.0141 (14)
C170.0551 (19)0.0497 (18)0.0444 (19)0.0337 (16)0.0031 (14)0.0112 (14)
C210.0215 (11)0.0272 (12)0.0234 (13)0.0116 (10)0.0014 (9)0.0006 (9)
C220.0237 (12)0.0308 (13)0.0256 (13)0.0133 (10)0.0003 (9)0.0014 (9)
C230.0342 (14)0.0343 (14)0.0204 (13)0.0182 (12)0.0020 (10)0.0001 (10)
C240.0399 (15)0.0364 (14)0.0285 (15)0.0150 (12)0.0059 (11)0.0089 (11)
C250.0301 (14)0.0330 (14)0.0341 (15)0.0092 (11)0.0059 (11)0.0053 (11)
C260.0203 (11)0.0263 (12)0.0271 (13)0.0098 (10)0.0006 (9)0.0025 (9)
C270.0275 (13)0.0284 (13)0.0264 (14)0.0073 (11)0.0018 (10)0.0011 (10)
C280.0304 (14)0.0461 (16)0.0375 (17)0.0154 (13)0.0090 (11)0.0001 (12)
C290.0365 (15)0.0486 (18)0.0470 (19)0.0261 (14)0.0102 (13)0.0049 (13)
C300.0304 (14)0.0485 (17)0.0537 (19)0.0265 (13)0.0020 (13)0.0002 (14)
C310.0289 (13)0.0370 (14)0.0404 (16)0.0201 (12)0.0009 (11)0.0022 (11)
C320.0454 (17)0.0344 (15)0.0379 (17)0.0116 (13)0.0063 (13)0.0070 (12)
C340.0472 (18)0.0336 (15)0.060 (2)0.0245 (14)0.0016 (14)0.0054 (13)
C350.0451 (17)0.061 (2)0.0450 (19)0.0355 (16)0.0085 (14)0.0049 (15)
C410.0259 (12)0.0234 (12)0.0278 (14)0.0145 (10)0.0016 (9)0.0002 (9)
C420.0310 (13)0.0302 (13)0.0252 (14)0.0181 (11)0.0044 (10)0.0033 (10)
C430.0337 (14)0.0329 (14)0.0225 (14)0.0169 (11)0.0018 (10)0.0001 (10)
C440.0478 (17)0.0362 (15)0.0286 (15)0.0198 (13)0.0016 (12)0.0079 (11)
C450.0430 (16)0.0272 (13)0.0359 (16)0.0200 (12)0.0025 (12)0.0039 (11)
C460.0274 (12)0.0254 (12)0.0277 (14)0.0163 (10)0.0014 (9)0.0008 (9)
C470.0409 (15)0.0332 (14)0.0271 (15)0.0235 (12)0.0016 (11)0.0004 (10)
C480.0518 (18)0.0512 (18)0.0376 (18)0.0351 (15)0.0068 (13)0.0059 (13)
C490.0374 (16)0.0556 (19)0.054 (2)0.0285 (15)0.0159 (14)0.0022 (15)
C500.0337 (15)0.0484 (18)0.059 (2)0.0271 (14)0.0025 (13)0.0012 (14)
C510.0269 (13)0.0354 (14)0.0419 (16)0.0171 (11)0.0029 (11)0.0005 (11)
C520.0554 (19)0.0383 (16)0.0386 (17)0.0249 (15)0.0042 (13)0.0097 (12)
C540.0322 (15)0.0359 (16)0.069 (2)0.0134 (13)0.0044 (14)0.0035 (15)
C550.0419 (17)0.057 (2)0.050 (2)0.0301 (16)0.0168 (14)0.0032 (15)
C570.0416 (17)0.056 (2)0.0405 (18)0.0230 (15)0.0140 (13)0.0007 (14)
Geometric parameters (Å, º) top
O13—C71.446 (3)C21—C261.561 (3)
O16—C21.443 (3)C22—C231.536 (4)
O18—C31.450 (3)C23—C371.506 (4)
O18—C61.459 (3)C23—C241.535 (4)
O33—C271.446 (3)C24—C251.540 (4)
O36—C221.439 (3)C25—C261.537 (3)
O38—C261.449 (3)C26—C271.534 (4)
O38—C231.462 (3)C27—C281.529 (4)
O53—C471.443 (3)C27—C321.530 (4)
O56—C421.443 (3)C28—C291.526 (4)
O58—C431.441 (3)C29—C301.529 (5)
O58—C461.453 (3)C30—C311.543 (4)
C1—C21.549 (4)C31—C341.534 (4)
C1—C61.560 (3)C31—C351.538 (4)
C1—C111.566 (3)C41—C421.545 (3)
C2—C31.533 (4)C41—C461.558 (3)
C3—C171.506 (4)C41—C511.560 (3)
C3—C41.550 (4)C42—C431.535 (4)
C4—C51.532 (4)C43—C571.506 (4)
C5—C61.540 (3)C43—C441.548 (4)
C6—C71.529 (4)C44—C451.537 (4)
C7—C81.527 (4)C45—C461.538 (3)
C7—C121.536 (4)C46—C471.532 (4)
C8—C91.535 (5)C47—C481.529 (4)
C9—C101.527 (5)C47—C521.539 (4)
C10—C111.545 (4)C48—C491.513 (5)
C11—C151.529 (4)C49—C501.528 (5)
C11—C141.542 (4)C50—C511.548 (4)
C21—C221.548 (3)C51—C541.536 (4)
C21—C311.559 (3)C51—C551.543 (4)
C3—O18—C697.68 (17)C27—C26—C25118.0 (2)
C26—O38—C2397.16 (17)O38—C26—C21101.27 (18)
C43—O58—C4697.86 (18)C27—C26—C21116.2 (2)
C2—C1—C6102.21 (19)C25—C26—C21110.9 (2)
C2—C1—C11116.0 (2)O33—C27—C28105.4 (2)
C6—C1—C11120.8 (2)O33—C27—C32108.2 (2)
O16—C2—C3112.4 (2)C28—C27—C32109.7 (2)
O16—C2—C1108.7 (2)O33—C27—C26108.74 (19)
C3—C2—C1101.6 (2)C28—C27—C26113.0 (2)
O18—C3—C17111.7 (2)C32—C27—C26111.4 (2)
O18—C3—C2100.9 (2)C29—C28—C27117.5 (2)
C17—C3—C2116.6 (2)C28—C29—C30113.9 (3)
O18—C3—C4102.3 (2)C29—C30—C31117.4 (2)
C17—C3—C4114.8 (2)C34—C31—C35106.9 (3)
C2—C3—C4108.8 (2)C34—C31—C30109.3 (2)
C5—C4—C3102.8 (2)C35—C31—C30107.1 (2)
C4—C5—C6101.5 (2)C34—C31—C21106.0 (2)
O18—C6—C7106.61 (19)C35—C31—C21115.4 (2)
O18—C6—C5100.70 (19)C30—C31—C21111.9 (2)
C7—C6—C5118.8 (2)C42—C41—C46101.84 (19)
O18—C6—C1100.63 (18)C42—C41—C51115.8 (2)
C7—C6—C1116.2 (2)C46—C41—C51121.5 (2)
C5—C6—C1110.7 (2)O56—C42—C43112.2 (2)
O13—C7—C8105.5 (2)O56—C42—C41109.0 (2)
O13—C7—C6109.49 (19)C43—C42—C41101.83 (19)
C8—C7—C6113.0 (2)O58—C43—C57111.8 (2)
O13—C7—C12108.1 (2)O58—C43—C42100.94 (19)
C8—C7—C12109.2 (2)C57—C43—C42116.7 (2)
C6—C7—C12111.2 (2)O58—C43—C44102.0 (2)
C7—C8—C9116.7 (2)C57—C43—C44114.8 (2)
C10—C9—C8113.7 (3)C42—C43—C44108.7 (2)
C9—C10—C11117.0 (3)C45—C44—C43103.0 (2)
C15—C11—C14106.5 (3)C44—C45—C46100.9 (2)
C15—C11—C10107.6 (2)O58—C46—C47107.0 (2)
C14—C11—C10109.4 (3)O58—C46—C45101.02 (19)
C15—C11—C1115.0 (2)C47—C46—C45117.8 (2)
C14—C11—C1106.2 (2)O58—C46—C41101.19 (18)
C10—C11—C1112.0 (2)C47—C46—C41116.6 (2)
C22—C21—C31115.6 (2)C45—C46—C41110.5 (2)
C22—C21—C26101.93 (19)O53—C47—C48105.4 (2)
C31—C21—C26121.5 (2)O53—C47—C46109.1 (2)
O36—C22—C23112.3 (2)C48—C47—C46112.8 (2)
O36—C22—C21109.2 (2)O53—C47—C52108.1 (2)
C23—C22—C21101.62 (19)C48—C47—C52109.9 (2)
O38—C23—C37111.6 (2)C46—C47—C52111.2 (2)
O38—C23—C24102.5 (2)C49—C48—C47117.5 (2)
C37—C23—C24115.0 (2)C48—C49—C50114.6 (3)
O38—C23—C22100.62 (19)C49—C50—C51117.5 (2)
C37—C23—C22116.5 (2)C54—C51—C55106.3 (3)
C24—C23—C22108.9 (2)C54—C51—C50109.5 (3)
C23—C24—C25103.0 (2)C55—C51—C50107.5 (2)
C26—C25—C24100.8 (2)C54—C51—C41106.1 (2)
O38—C26—C27106.48 (19)C55—C51—C41115.2 (2)
O38—C26—C25101.17 (19)C50—C51—C41112.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O16i0.93 (1)2.33 (1)3.122 (3)143 (1)
O16—H16···O16ii0.96 (1)2.10 (1)3.032 (3)163 (1)
O33—H33···O36iii0.92 (1)2.37 (1)3.134 (4)140 (1)
O36—H36···O36iv0.99 (1)2.03 (1)3.008 (3)171 (1)
O53—H53···O56v0.88 (1)2.39 (1)3.106 (3)139 (1)
O56—H56···O56vi0.96 (1)2.06 (1)3.018 (3)175 (1)
Symmetry codes: (i) x+y1, x, z+1/3; (ii) y, xy+1, z1/3; (iii) y+1, xy+1, z1/3; (iv) x+y, x+1, z+1/3; (v) x+y1, x+1, z+1/3; (vi) y+1, xy+2, z1/3.

Experimental details

Crystal data
Chemical formulaC15H26O3
Mr254.37
Crystal system, space groupTrigonal, P32
Temperature (K)298
a, c (Å)21.266 (9), 7.873 (5)
V3)3083.5 (3)
Z9
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.25 × 0.20
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9812, 3985, 3740
Rint0.052
(sin θ/λ)max1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.090, 1.09
No. of reflections3985
No. of parameters485
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.23

Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), maXus (Mackay et al., 1999).

Selected geometric parameters (Å, º) top
C1—C61.560 (3)C23—C371.506 (4)
C1—C111.566 (3)C41—C461.558 (3)
C3—C171.506 (4)C41—C511.560 (3)
C21—C311.559 (3)C43—C571.506 (4)
C21—C261.561 (3)
C6—C1—C11120.8 (2)C46—C41—C51121.5 (2)
C31—C21—C26121.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O16i0.931 (2)2.325 (2)3.122 (3)143.4 (1)
O16—H16···O16ii0.959 (2)2.102 (2)3.032 (3)163.4 (1)
O33—H33···O36iii0.920 (1)2.370 (2)3.134 (4)140.4 (1)
O36—H36···O36iv0.988 (1)2.027 (2)3.008 (3)171.2 (1)
O53—H53···O56v0.876 (1)2.393 (2)3.106 (3)138.6 (1)
O56—H56···O56vi0.958 (1)2.062 (2)3.018 (3)175.2 (1)
Symmetry codes: (i) x+y1, x, z+1/3; (ii) y, xy+1, z1/3; (iii) y+1, xy+1, z1/3; (iv) x+y, x+1, z+1/3; (v) x+y1, x+1, z+1/3; (vi) y+1, xy+2, z1/3.
 

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