(2-tert-Butyl-5-hy-droxy-methyl-1,3-dioxan-5-yl)methanol.

In the title compound, C(10)H(20)O(4), the dioxane ring adopts a chair conformation. The tert-butyl group occupies an equatorial position, and is staggered with respect to the O atoms of the dioxane ring. In the crystal, mol-ecules are connected by O-H⋯O hydrogen-bonds into zigzag chains of R(4) (4)(8) and R(2) (2)(12) ring motifs that run parallel to the a axis.

Related literature

For background information on the synthesis and properties of 1,3-dioxanes, see: Anderson (1967 ▶); Bailey et al. (1978 ▶); Juaristi et al. (1987 ▶, 1989 ▶); Vázquez-Hernández et al. (2004 ▶). For the crystal structure of a similar compound, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C10H20O4

M = 204.26

Triclinic,

a = 5.8337 (10) Å

b = 6.1408 (9) Å

c = 17.941 (3) Å

α = 81.468 (12)°

β = 87.335 (14)°

γ = 62.606 (13)°

V = 564.16 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.73 × 0.63 × 0.20 mm

Data collection

Siemens P4 diffractometer

Absorption correction: empirical (using intensity measurements) (XEMP in SHELXTL; Sheldrick, 2008 ▶) T min = 0.335, T max = 0.466

3581 measured reflections

3283 independent reflections

2593 reflections with I > 2σ(I)

R int = 0.013

3 standard reflections every 97 reflections intensity decay: 5.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.193

S = 1.42

3283 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202541X/pk2419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202541X/pk2419Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202541X/pk2419Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H20O4	Z = 2
Mr = 204.26	F(000) = 224
Triclinic, P1	Dx = 1.202 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8337 (10) Å	Cell parameters from 52 reflections
b = 6.1408 (9) Å	θ = 5.6–12.5°
c = 17.941 (3) Å	µ = 0.09 mm−1
α = 81.468 (12)°	T = 298 K
β = 87.335 (14)°	Prismatic, colorless
γ = 62.606 (13)°	0.73 × 0.63 × 0.20 mm
V = 564.16 (15) Å3

Siemens P4 diffractometer	2593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 30.0°, θmin = 2.3°
2θ/ω scans	h = 0→8
Absorption correction: empirical (using intensity measurements) (XEMP in SHELXTL; Sheldrick, 2008)	k = −7→8
Tmin = 0.335, Tmax = 0.466	l = −25→25
3581 measured reflections	3 standard reflections every 97 reflections
3283 independent reflections	intensity decay: 5.8%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.42	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3283 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.19141 (17)	0.04289 (16)	0.28059 (4)	0.0416 (2)
O2	−0.01630 (17)	−0.14442 (16)	0.22771 (4)	0.0413 (2)
O3	−0.31024 (19)	0.4084 (2)	0.08767 (6)	0.0652 (4)
H3A	−0.2724	0.4774	0.0500	0.098*
O4	0.2736 (2)	0.3620 (2)	0.05181 (5)	0.0572 (3)
H4A	0.4138	0.3393	0.0675	0.086*
C1	0.1581 (2)	−0.1720 (2)	0.28510 (6)	0.0374 (3)
H1A	0.3254	−0.3144	0.2793	0.045*
C2	0.2949 (2)	0.0938 (2)	0.21038 (6)	0.0422 (3)
H2A	0.4652	−0.0414	0.2051	0.051*
H2B	0.3125	0.2437	0.2095	0.051*
C3	0.1194 (2)	0.12605 (19)	0.14454 (6)	0.0336 (2)
C4	0.0755 (3)	−0.1038 (2)	0.15426 (6)	0.0439 (3)
H4B	−0.0495	−0.0829	0.1165	0.053*
H4C	0.2363	−0.2477	0.1466	0.053*
C5	0.0515 (2)	−0.2160 (2)	0.36206 (6)	0.0417 (3)
C6	−0.2078 (3)	0.0058 (3)	0.37302 (8)	0.0546 (3)
H6A	−0.3292	0.0278	0.3347	0.082*
H6B	−0.1852	0.1523	0.3694	0.082*
H6C	−0.2717	−0.0234	0.4218	0.082*
C7	0.2463 (3)	−0.2507 (3)	0.42305 (8)	0.0663 (4)
H7A	0.2672	−0.1033	0.4196	0.099*
H7B	0.4096	−0.3887	0.4158	0.099*
H7C	0.1839	−0.2816	0.4719	0.099*
C8	0.0168 (4)	−0.4500 (3)	0.36665 (10)	0.0688 (5)
H8A	−0.1058	−0.4263	0.3285	0.103*
H8B	−0.0452	−0.4824	0.4154	0.103*
H8C	0.1796	−0.5881	0.3589	0.103*
C10	0.2505 (3)	0.1391 (3)	0.06975 (7)	0.0467 (3)
H10A	0.4212	−0.0014	0.0720	0.056*
H10B	0.1517	0.1273	0.0299	0.056*
C9	−0.1367 (2)	0.3603 (2)	0.14803 (7)	0.0433 (3)
H9A	−0.2177	0.3427	0.1954	0.052*
H9B	−0.1020	0.5009	0.1468	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0540 (5)	0.0534 (5)	0.0310 (4)	−0.0366 (4)	−0.0015 (3)	−0.0038 (3)
O2	0.0566 (5)	0.0497 (5)	0.0326 (4)	−0.0369 (4)	0.0046 (3)	−0.0080 (3)
O3	0.0482 (5)	0.0904 (8)	0.0554 (6)	−0.0377 (5)	−0.0154 (4)	0.0201 (5)
O4	0.0621 (6)	0.0766 (7)	0.0491 (5)	−0.0501 (5)	−0.0003 (4)	0.0073 (4)
C1	0.0408 (5)	0.0386 (5)	0.0343 (5)	−0.0200 (4)	0.0022 (4)	−0.0036 (4)
C2	0.0432 (6)	0.0585 (7)	0.0354 (5)	−0.0339 (5)	−0.0020 (4)	0.0003 (5)
C3	0.0378 (5)	0.0412 (5)	0.0294 (5)	−0.0245 (4)	0.0032 (4)	−0.0053 (4)
C4	0.0638 (7)	0.0475 (6)	0.0339 (5)	−0.0357 (6)	0.0066 (5)	−0.0119 (4)
C5	0.0498 (6)	0.0455 (6)	0.0339 (5)	−0.0264 (5)	0.0042 (4)	−0.0027 (4)
C6	0.0543 (7)	0.0636 (8)	0.0489 (7)	−0.0281 (6)	0.0139 (6)	−0.0168 (6)
C7	0.0694 (9)	0.0933 (12)	0.0373 (6)	−0.0425 (9)	−0.0085 (6)	0.0083 (7)
C8	0.1062 (13)	0.0573 (8)	0.0570 (8)	−0.0518 (9)	0.0223 (8)	−0.0066 (6)
C10	0.0540 (7)	0.0600 (7)	0.0355 (5)	−0.0345 (6)	0.0090 (5)	−0.0076 (5)
C9	0.0411 (6)	0.0465 (6)	0.0426 (6)	−0.0218 (5)	0.0004 (5)	−0.0012 (4)

O1—C1	1.4100 (13)	C4—H4C	0.9700
O1—C2	1.4266 (13)	C5—C6	1.529 (2)
O2—C1	1.4181 (14)	C5—C8	1.5307 (19)
O2—C4	1.4301 (13)	C5—C7	1.5356 (19)
O3—C9	1.4204 (15)	C6—H6A	0.9600
O3—H3A	0.8200	C6—H6B	0.9600
O4—C10	1.4248 (16)	C6—H6C	0.9600
O4—H4A	0.8200	C7—H7A	0.9600
C1—C5	1.5267 (15)	C7—H7B	0.9600
C1—H1A	0.9800	C7—H7C	0.9600
C2—C3	1.5297 (15)	C8—H8A	0.9600
C2—H2A	0.9700	C8—H8B	0.9600
C2—H2B	0.9700	C8—H8C	0.9600
C3—C10	1.5235 (15)	C10—H10A	0.9700
C3—C9	1.5314 (16)	C10—H10B	0.9700
C3—C4	1.5309 (15)	C9—H9A	0.9700
C4—H4B	0.9700	C9—H9B	0.9700
C1—O1—C2	112.27 (8)	C6—C5—C7	109.52 (12)
C1—O2—C4	111.54 (9)	C8—C5—C7	110.10 (12)
C9—O3—H3A	109.5	C5—C6—H6A	109.5
C10—O4—H4A	109.5	C5—C6—H6B	109.5
O1—C1—O2	110.58 (8)	H6A—C6—H6B	109.5
O1—C1—C5	109.07 (9)	C5—C6—H6C	109.5
O2—C1—C5	109.32 (9)	H6A—C6—H6C	109.5
O1—C1—H1A	109.3	H6B—C6—H6C	109.5
O2—C1—H1A	109.3	C5—C7—H7A	109.5
C5—C1—H1A	109.3	C5—C7—H7B	109.5
O1—C2—C3	110.78 (8)	H7A—C7—H7B	109.5
O1—C2—H2A	109.5	C5—C7—H7C	109.5
C3—C2—H2A	109.5	H7A—C7—H7C	109.5
O1—C2—H2B	109.5	H7B—C7—H7C	109.5
C3—C2—H2B	109.5	C5—C8—H8A	109.5
H2A—C2—H2B	108.1	C5—C8—H8B	109.5
C10—C3—C2	110.54 (9)	H8A—C8—H8B	109.5
C10—C3—C9	111.37 (9)	C5—C8—H8C	109.5
C2—C3—C9	108.81 (9)	H8A—C8—H8C	109.5
C10—C3—C4	108.60 (9)	H8B—C8—H8C	109.5
C2—C3—C4	106.80 (9)	O4—C10—C3	112.63 (10)
C9—C3—C4	110.62 (9)	O4—C10—H10A	109.1
O2—C4—C3	111.25 (9)	C3—C10—H10A	109.1
O2—C4—H4B	109.4	O4—C10—H10B	109.1
C3—C4—H4B	109.4	C3—C10—H10B	109.1
O2—C4—H4C	109.4	H10A—C10—H10B	107.8
C3—C4—H4C	109.4	O3—C9—C3	112.71 (10)
H4B—C4—H4C	108.0	O3—C9—H9A	109.0
C1—C5—C6	110.31 (10)	C3—C9—H9A	109.0
C1—C5—C8	108.76 (10)	O3—C9—H9B	109.0
C6—C5—C8	109.86 (12)	C3—C9—H9B	109.0
C1—C5—C7	108.27 (10)	H9A—C9—H9B	107.8
C2—O1—C1—O2	−60.72 (11)	O1—C1—C5—C6	59.66 (13)
C2—O1—C1—C5	179.03 (9)	O2—C1—C5—C6	−61.36 (12)
C4—O2—C1—O1	60.20 (11)	O1—C1—C5—C8	−179.79 (11)
C4—O2—C1—C5	−179.71 (8)	O2—C1—C5—C8	59.20 (14)
C1—O1—C2—C3	58.43 (12)	O1—C1—C5—C7	−60.16 (13)
O1—C2—C3—C10	−170.96 (9)	O2—C1—C5—C7	178.82 (10)
O1—C2—C3—C9	66.45 (12)	C2—C3—C10—O4	−69.64 (13)
O1—C2—C3—C4	−52.99 (12)	C9—C3—C10—O4	51.45 (13)
C1—O2—C4—C3	−58.05 (13)	C4—C3—C10—O4	173.51 (10)
C10—C3—C4—O2	172.44 (9)	C10—C3—C9—O3	56.51 (12)
C2—C3—C4—O2	53.21 (13)	C2—C3—C9—O3	178.60 (9)
C9—C3—C4—O2	−65.05 (12)	C4—C3—C9—O3	−64.38 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4i	0.82	1.94	2.7346 (14)	162
O4—H4A···O3ii	0.82	1.91	2.6878 (15)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4i	0.82	1.94	2.7346 (14)	162
O4—H4A⋯O3ii	0.82	1.91	2.6878 (15)	159

Symmetry codes: (i) ; (ii) .