1,1′,1′′-[(5RS,6RS)-6-Hydr­oxy-6-methyl-3,4,5,6-tetra­hydro-2H-pyran-3,3,5-tri­yl]triethanone

In the title compound, C₁₂H₁₈O₅, the ring has a chair conformation, with endocyclic torsion angle magnitudes in the range 47.7 (3)–66.7 (2)°. The OH group donates an inter­molecular hydrogen bond to a C=O group with an O...O distance of 2.791 (3) Å, forming chains.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.106
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.25
PLAT128_ALERT_4_C Non-standard setting of Space group Pc      ....    Pn

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               1796
           Count of symmetry unique reflns         1800
           Completeness (_total/calc)             99.78%
           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
PLAT792_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C2     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,1',1''-[(5R,6R)-6-Hydroxy-6-methyl-3,4,5,6-tetrahydro- 2H-pyran-3,3,5-triyl]triethanone

Crystal data

C12H18O5	F(000) = 260
Mr = 242.26	Dx = 1.311 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 1738 reflections
a = 7.598 (2) Å	θ = 2.5–30.0°
b = 8.813 (3) Å	µ = 0.10 mm^−1
c = 9.169 (2) Å	T = 120 K
β = 91.26 (2)°	Lath, colorless
V = 613.8 (3) Å^3	0.46 × 0.07 × 0.05 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	1588 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 30.0°, θmin = 3.2°
ω scans with κ offsets	h = −10→10
6461 measured reflections	k = −12→9
1796 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.2367P] where P = (Fo^2 + 2Fc^2)/3
1796 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.45 e Å^−3
2 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1656 (2)	0.2610 (2)	0.24547 (19)	0.0205 (4)
O2	0.3818 (2)	0.1034 (2)	0.14888 (19)	0.0211 (4)
H2	0.3066	0.0561	0.0981	0.032*
O3	0.6059 (3)	0.0523 (3)	0.5097 (3)	0.0368 (5)
O4	0.3071 (3)	0.5370 (3)	0.5145 (2)	0.0338 (5)
O5	0.3491 (3)	0.6508 (3)	0.0520 (2)	0.0379 (5)
C1	0.3040 (3)	0.1551 (3)	0.2779 (3)	0.0186 (5)
C2	0.4495 (3)	0.2361 (3)	0.3707 (2)	0.0163 (4)
H2A	0.3980	0.2597	0.4675	0.020*
C3	0.5066 (3)	0.3870 (3)	0.3041 (3)	0.0176 (5)
H3A	0.5786	0.3668	0.2176	0.021*
H3B	0.5807	0.4431	0.3761	0.021*
C4	0.3477 (3)	0.4854 (3)	0.2588 (3)	0.0178 (5)
C5	0.2215 (3)	0.3897 (3)	0.1647 (3)	0.0200 (5)
H5A	0.1180	0.4514	0.1348	0.024*
H5B	0.2814	0.3559	0.0756	0.024*
C6	0.2164 (3)	0.0275 (3)	0.3598 (3)	0.0267 (6)
H6A	0.1299	−0.0228	0.2954	0.040*
H6B	0.1571	0.0688	0.4449	0.040*
H6C	0.3057	−0.0462	0.3921	0.040*
C7	0.6035 (3)	0.1282 (3)	0.3987 (3)	0.0224 (5)
C8	0.7479 (4)	0.1169 (3)	0.2907 (3)	0.0279 (6)
H8A	0.8311	0.2007	0.3063	0.042*
H8B	0.6975	0.1228	0.1916	0.042*
H8C	0.8096	0.0200	0.3036	0.042*
C9	0.2494 (3)	0.5486 (3)	0.3917 (3)	0.0218 (5)
C10	0.0762 (4)	0.6266 (3)	0.3594 (3)	0.0298 (6)
H10A	−0.0185	0.5511	0.3565	0.045*
H10B	0.0813	0.6782	0.2649	0.045*
H10C	0.0533	0.7012	0.4360	0.045*
C11	0.4126 (3)	0.6231 (3)	0.1709 (3)	0.0214 (5)
C12	0.5579 (4)	0.7183 (3)	0.2368 (4)	0.0331 (6)
H12A	0.6715	0.6693	0.2201	0.050*
H12B	0.5405	0.7286	0.3419	0.050*
H12C	0.5566	0.8189	0.1914	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0143 (8)	0.0194 (9)	0.0276 (9)	0.0005 (7)	−0.0032 (7)	0.0027 (7)
O2	0.0183 (8)	0.0215 (9)	0.0234 (8)	−0.0019 (7)	−0.0040 (7)	−0.0068 (7)
O3	0.0276 (10)	0.0362 (12)	0.0462 (12)	0.0012 (9)	−0.0100 (9)	0.0207 (10)
O4	0.0340 (11)	0.0405 (12)	0.0267 (10)	0.0043 (10)	−0.0020 (8)	−0.0064 (9)
O5	0.0432 (13)	0.0379 (12)	0.0321 (10)	−0.0081 (10)	−0.0105 (9)	0.0165 (9)
C1	0.0142 (10)	0.0175 (12)	0.0239 (12)	−0.0006 (9)	−0.0019 (9)	0.0010 (9)
C2	0.0152 (11)	0.0155 (11)	0.0181 (11)	0.0003 (9)	−0.0032 (8)	0.0000 (9)
C3	0.0177 (10)	0.0150 (11)	0.0200 (11)	−0.0010 (9)	−0.0021 (9)	0.0019 (9)
C4	0.0172 (10)	0.0164 (11)	0.0198 (11)	0.0010 (9)	−0.0021 (8)	0.0001 (9)
C5	0.0173 (10)	0.0192 (12)	0.0232 (11)	0.0006 (10)	−0.0048 (9)	0.0023 (9)
C6	0.0193 (12)	0.0227 (13)	0.0381 (15)	−0.0044 (10)	0.0002 (10)	0.0054 (11)
C7	0.0194 (11)	0.0163 (11)	0.0311 (13)	−0.0029 (9)	−0.0089 (10)	−0.0007 (10)
C8	0.0175 (11)	0.0250 (13)	0.0410 (16)	0.0047 (10)	−0.0031 (11)	−0.0078 (12)
C9	0.0231 (12)	0.0182 (12)	0.0241 (12)	−0.0040 (10)	0.0032 (9)	−0.0003 (9)
C10	0.0234 (13)	0.0282 (14)	0.0379 (15)	0.0039 (11)	0.0046 (11)	0.0000 (12)
C11	0.0238 (12)	0.0165 (11)	0.0239 (12)	0.0014 (10)	0.0013 (9)	0.0023 (10)
C12	0.0338 (14)	0.0238 (14)	0.0415 (16)	−0.0044 (12)	−0.0026 (12)	0.0062 (13)

Geometric parameters (Å, º)

O1—C5	1.424 (3)	C5—H5A	0.9900
O1—C1	1.432 (3)	C5—H5B	0.9900
O2—C1	1.410 (3)	C6—H6A	0.9800
O2—H2	0.8400	C6—H6B	0.9800
O3—C7	1.217 (3)	C6—H6C	0.9800
O4—C9	1.204 (3)	C7—C8	1.498 (4)
O5—C11	1.207 (3)	C8—H8A	0.9800
C1—C6	1.515 (4)	C8—H8B	0.9800
C1—C2	1.554 (3)	C8—H8C	0.9800
C2—C7	1.525 (3)	C9—C10	1.508 (4)
C2—C3	1.530 (3)	C10—H10A	0.9800
C2—H2A	1.0000	C10—H10B	0.9800
C3—C4	1.536 (3)	C10—H10C	0.9800
C3—H3A	0.9900	C11—C12	1.503 (4)
C3—H3B	0.9900	C12—H12A	0.9800
C4—C5	1.529 (3)	C12—H12B	0.9800
C4—C11	1.543 (3)	C12—H12C	0.9800
C4—C9	1.547 (4)
C5—O1—C1	113.62 (18)	C1—C6—H6B	109.5
C1—O2—H2	109.5	H6A—C6—H6B	109.5
O2—C1—O1	110.82 (19)	C1—C6—H6C	109.5
O2—C1—C6	111.9 (2)	H6A—C6—H6C	109.5
O1—C1—C6	105.0 (2)	H6B—C6—H6C	109.5
O2—C1—C2	107.56 (19)	O3—C7—C8	121.2 (2)
O1—C1—C2	108.98 (19)	O3—C7—C2	118.8 (2)
C6—C1—C2	112.6 (2)	C8—C7—C2	120.0 (2)
C7—C2—C3	112.73 (19)	C7—C8—H8A	109.5
C7—C2—C1	109.87 (19)	C7—C8—H8B	109.5
C3—C2—C1	112.65 (18)	H8A—C8—H8B	109.5
C7—C2—H2A	107.1	C7—C8—H8C	109.5
C3—C2—H2A	107.1	H8A—C8—H8C	109.5
C1—C2—H2A	107.1	H8B—C8—H8C	109.5
C2—C3—C4	111.76 (19)	O4—C9—C10	121.4 (2)
C2—C3—H3A	109.3	O4—C9—C4	122.3 (2)
C4—C3—H3A	109.3	C10—C9—C4	116.4 (2)
C2—C3—H3B	109.3	C9—C10—H10A	109.5
C4—C3—H3B	109.3	C9—C10—H10B	109.5
H3A—C3—H3B	107.9	H10A—C10—H10B	109.5
C5—C4—C3	108.7 (2)	C9—C10—H10C	109.5
C5—C4—C11	110.1 (2)	H10A—C10—H10C	109.5
C3—C4—C11	109.1 (2)	H10B—C10—H10C	109.5
C5—C4—C9	109.6 (2)	O5—C11—C12	121.7 (2)
C3—C4—C9	112.36 (19)	O5—C11—C4	120.3 (2)
C11—C4—C9	107.1 (2)	C12—C11—C4	118.0 (2)
O1—C5—C4	109.7 (2)	C11—C12—H12A	109.5
O1—C5—H5A	109.7	C11—C12—H12B	109.5
C4—C5—H5A	109.7	H12A—C12—H12B	109.5
O1—C5—H5B	109.7	C11—C12—H12C	109.5
C4—C5—H5B	109.7	H12A—C12—H12C	109.5
H5A—C5—H5B	108.2	H12B—C12—H12C	109.5
C1—C6—H6A	109.5
C5—O1—C1—O2	−57.8 (3)	C9—C4—C5—O1	−63.9 (2)
C5—O1—C1—C6	−178.7 (2)	C3—C2—C7—O3	140.7 (2)
C5—O1—C1—C2	60.4 (2)	C1—C2—C7—O3	−92.7 (3)
O2—C1—C2—C7	−56.4 (2)	C3—C2—C7—C8	−39.3 (3)
O1—C1—C2—C7	−176.58 (19)	C1—C2—C7—C8	87.2 (3)
C6—C1—C2—C7	67.4 (3)	C5—C4—C9—O4	130.1 (3)
O2—C1—C2—C3	70.2 (2)	C3—C4—C9—O4	9.1 (3)
O1—C1—C2—C3	−50.0 (2)	C11—C4—C9—O4	−110.6 (3)
C6—C1—C2—C3	−166.0 (2)	C5—C4—C9—C10	−50.1 (3)
C7—C2—C3—C4	172.71 (19)	C3—C4—C9—C10	−171.0 (2)
C1—C2—C3—C4	47.7 (3)	C11—C4—C9—C10	69.2 (3)
C2—C3—C4—C5	−51.1 (3)	C5—C4—C11—O5	7.7 (3)
C2—C3—C4—C11	−171.08 (19)	C3—C4—C11—O5	126.8 (3)
C2—C3—C4—C9	70.4 (3)	C9—C4—C11—O5	−111.4 (3)
C1—O1—C5—C4	−66.7 (2)	C5—C4—C11—C12	−171.2 (2)
C3—C4—C5—O1	59.2 (2)	C3—C4—C11—C12	−52.0 (3)
C11—C4—C5—O1	178.63 (19)	C9—C4—C11—C12	69.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^i	0.84	1.96	2.791 (3)	170

Symmetry code: (i) x−1/2, −y, z−1/2.