(5-n-Hexyl-2-hydroxymethyl-1,3-dioxan-2-yl)methanol.

In the title compound, C(12)H(24)O(4), the dioxane ring adopts a chair conformation; the n-hexyl chain, which occupies an equatorial position, has an extended zigzag conformation. In the crystal, mol-ecules are connected by O-H⋯O hydrogen-bonds into a zigzag chain running along the b axis, giving rise to a herringbone pattern.

Related literature

For a related structure, see: Luo et al. (2008 ▶).

Experimental

Crystal data

C12H24O4

M = 232.31

Monoclinic,

a = 13.6602 (10) Å

b = 5.9370 (5) Å

c = 16.4268 (12) Å

β = 97.737 (1)°

V = 1320.10 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

7438 measured reflections

2862 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.173

S = 1.06

2862 reflections

154 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041401/bt5377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041401/bt5377Isup2.hkl

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

C12H24O4	F(000) = 512
Mr = 232.31	Dx = 1.169 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2106 reflections
a = 13.6602 (10) Å	θ = 2.5–27.0°
b = 5.9370 (5) Å	µ = 0.09 mm−1
c = 16.4268 (12) Å	T = 173 K
β = 97.737 (1)°	Prism, colorless
V = 1320.10 (18) Å3	0.40 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	1755 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 27.1°, θmin = 1.8°
ω scans	h = −17→17
7438 measured reflections	k = −7→7
2862 independent reflections	l = −20→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0932P)2] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.21236 (8)	1.1104 (2)	0.46544 (7)	0.0274 (3)
O2	0.08583 (9)	1.3743 (2)	0.45699 (9)	0.0449 (4)
O3	0.25706 (13)	1.7500 (2)	0.65335 (8)	0.0449 (4)
H3	0.2562 (18)	1.699 (4)	0.7006 (8)	0.063 (8)*
O4	0.24968 (15)	1.1821 (2)	0.68721 (8)	0.0551 (5)
H4	0.257 (2)	1.051 (2)	0.6681 (16)	0.083 (9)*
C1	0.22572 (13)	1.4192 (3)	0.56451 (10)	0.0259 (4)
C2	0.29973 (15)	1.5895 (3)	0.60499 (12)	0.0358 (5)
H2A	0.3529	1.5084	0.6402	0.043*
H2B	0.3302	1.6693	0.5618	0.043*
C3	0.17790 (16)	1.2926 (3)	0.62952 (12)	0.0390 (5)
H3A	0.1398	1.3998	0.6590	0.047*
H3B	0.1313	1.1794	0.6024	0.047*
C4	0.14640 (15)	1.5360 (3)	0.50544 (12)	0.0387 (5)
H4A	0.1046	1.6292	0.5369	0.046*
H4B	0.1780	1.6370	0.4687	0.046*
C5	0.27918 (13)	1.2561 (3)	0.51385 (11)	0.0275 (4)
H5A	0.3173	1.3429	0.4774	0.033*
H5B	0.3264	1.1648	0.5512	0.033*
C6	0.14157 (13)	1.2334 (3)	0.41238 (11)	0.0321 (5)
H6	0.1756	1.3257	0.3737	0.039*
C7	0.07331 (14)	1.0673 (4)	0.36474 (12)	0.0391 (5)
H7A	0.0179	1.1508	0.3333	0.047*
H7B	0.0452	0.9678	0.4040	0.047*
C8	0.12197 (14)	0.9224 (3)	0.30569 (12)	0.0342 (5)
H8A	0.1780	0.8402	0.3368	0.041*
H8B	0.1489	1.0211	0.2655	0.041*
C9	0.05174 (14)	0.7536 (4)	0.25968 (13)	0.0393 (5)
H9A	0.0248	0.6562	0.3002	0.047*
H9B	−0.0043	0.8368	0.2290	0.047*
C10	0.09718 (14)	0.6053 (4)	0.20005 (11)	0.0355 (5)
H10A	0.1277	0.7026	0.1615	0.043*
H10B	0.1505	0.5148	0.2311	0.043*
C11	0.02531 (15)	0.4480 (4)	0.15108 (14)	0.0457 (6)
H11A	−0.0268	0.5389	0.1186	0.055*
H11B	−0.0069	0.3545	0.1897	0.055*
C12	0.07088 (17)	0.2939 (4)	0.09337 (13)	0.0473 (6)
H12A	0.1047	0.3843	0.0558	0.071*
H12B	0.0189	0.2039	0.0617	0.071*
H12C	0.1185	0.1936	0.1252	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0304 (7)	0.0258 (7)	0.0243 (6)	0.0012 (5)	−0.0030 (5)	−0.0047 (5)
O2	0.0375 (8)	0.0450 (9)	0.0482 (9)	0.0139 (7)	−0.0091 (7)	−0.0197 (7)
O3	0.0890 (12)	0.0223 (7)	0.0231 (7)	−0.0018 (7)	0.0063 (8)	−0.0032 (6)
O4	0.1172 (14)	0.0244 (8)	0.0241 (7)	−0.0002 (9)	0.0109 (8)	0.0009 (6)
C1	0.0359 (10)	0.0209 (9)	0.0211 (9)	−0.0008 (7)	0.0041 (7)	−0.0013 (7)
C2	0.0487 (12)	0.0298 (11)	0.0290 (10)	−0.0094 (9)	0.0054 (9)	−0.0058 (8)
C3	0.0559 (13)	0.0301 (11)	0.0349 (11)	−0.0091 (9)	0.0200 (10)	−0.0060 (8)
C4	0.0477 (12)	0.0305 (11)	0.0352 (11)	0.0093 (9)	−0.0046 (9)	−0.0078 (8)
C5	0.0278 (9)	0.0316 (10)	0.0221 (9)	−0.0014 (7)	−0.0002 (7)	−0.0045 (7)
C6	0.0344 (10)	0.0338 (11)	0.0259 (10)	0.0041 (8)	−0.0038 (8)	−0.0051 (8)
C7	0.0301 (10)	0.0468 (13)	0.0373 (11)	0.0054 (9)	−0.0064 (9)	−0.0119 (9)
C8	0.0335 (10)	0.0400 (12)	0.0269 (9)	−0.0021 (9)	−0.0034 (8)	−0.0051 (8)
C9	0.0288 (10)	0.0498 (13)	0.0364 (11)	0.0018 (9)	−0.0059 (9)	−0.0127 (9)
C10	0.0338 (10)	0.0437 (12)	0.0282 (10)	−0.0045 (9)	0.0014 (8)	−0.0039 (9)
C11	0.0353 (11)	0.0528 (14)	0.0464 (12)	−0.0015 (10)	−0.0035 (9)	−0.0196 (10)
C12	0.0541 (13)	0.0490 (14)	0.0388 (12)	−0.0057 (11)	0.0059 (11)	−0.0131 (10)

O1—C6	1.415 (2)	C6—C7	1.503 (3)
O1—C5	1.421 (2)	C6—H6	1.0000
O2—C6	1.403 (2)	C7—C8	1.516 (3)
O2—C4	1.436 (2)	C7—H7A	0.9900
O3—C2	1.415 (2)	C7—H7B	0.9900
O3—H3	0.84 (1)	C8—C9	1.517 (3)
O4—C3	1.428 (3)	C8—H8A	0.9900
O4—H4	0.85 (1)	C8—H8B	0.9900
C1—C2	1.519 (2)	C9—C10	1.511 (3)
C1—C4	1.521 (3)	C9—H9A	0.9900
C1—C3	1.523 (2)	C9—H9B	0.9900
C1—C5	1.525 (2)	C10—C11	1.507 (3)
C2—H2A	0.9900	C10—H10A	0.9900
C2—H2B	0.9900	C10—H10B	0.9900
C3—H3A	0.9900	C11—C12	1.510 (3)
C3—H3B	0.9900	C11—H11A	0.9900
C4—H4A	0.9900	C11—H11B	0.9900
C4—H4B	0.9900	C12—H12A	0.9800
C5—H5A	0.9900	C12—H12B	0.9800
C5—H5B	0.9900	C12—H12C	0.9800
C6—O1—C5	111.39 (13)	O1—C6—H6	109.7
C6—O2—C4	112.06 (13)	C7—C6—H6	109.7
C2—O3—H3	109.7 (18)	C6—C7—C8	114.28 (15)
C3—O4—H4	106.1 (19)	C6—C7—H7A	108.7
C2—C1—C4	110.53 (16)	C8—C7—H7A	108.7
C2—C1—C3	110.16 (14)	C6—C7—H7B	108.7
C4—C1—C3	109.65 (15)	C8—C7—H7B	108.7
C2—C1—C5	108.80 (14)	H7A—C7—H7B	107.6
C4—C1—C5	107.08 (14)	C7—C8—C9	113.05 (16)
C3—C1—C5	110.57 (15)	C7—C8—H8A	109.0
O3—C2—C1	113.19 (15)	C9—C8—H8A	109.0
O3—C2—H2A	108.9	C7—C8—H8B	109.0
C1—C2—H2A	108.9	C9—C8—H8B	109.0
O3—C2—H2B	108.9	H8A—C8—H8B	107.8
C1—C2—H2B	108.9	C10—C9—C8	114.86 (16)
H2A—C2—H2B	107.8	C10—C9—H9A	108.6
O4—C3—C1	111.78 (16)	C8—C9—H9A	108.6
O4—C3—H3A	109.3	C10—C9—H9B	108.6
C1—C3—H3A	109.3	C8—C9—H9B	108.6
O4—C3—H3B	109.3	H9A—C9—H9B	107.5
C1—C3—H3B	109.3	C11—C10—C9	114.35 (16)
H3A—C3—H3B	107.9	C11—C10—H10A	108.7
O2—C4—C1	110.89 (15)	C9—C10—H10A	108.7
O2—C4—H4A	109.5	C11—C10—H10B	108.7
C1—C4—H4A	109.5	C9—C10—H10B	108.7
O2—C4—H4B	109.5	H10A—C10—H10B	107.6
C1—C4—H4B	109.5	C10—C11—C12	114.61 (17)
H4A—C4—H4B	108.0	C10—C11—H11A	108.6
O1—C5—C1	111.91 (13)	C12—C11—H11A	108.6
O1—C5—H5A	109.2	C10—C11—H11B	108.6
C1—C5—H5A	109.2	C12—C11—H11B	108.6
O1—C5—H5B	109.2	H11A—C11—H11B	107.6
C1—C5—H5B	109.2	C11—C12—H12A	109.5
H5A—C5—H5B	107.9	C11—C12—H12B	109.5
O2—C6—O1	111.11 (14)	H12A—C12—H12B	109.5
O2—C6—C7	108.74 (14)	C11—C12—H12C	109.5
O1—C6—C7	107.86 (15)	H12A—C12—H12C	109.5
O2—C6—H6	109.7	H12B—C12—H12C	109.5
C4—C1—C2—O3	62.40 (19)	C4—C1—C5—O1	−52.67 (19)
C3—C1—C2—O3	−58.9 (2)	C3—C1—C5—O1	66.74 (19)
C5—C1—C2—O3	179.70 (15)	C4—O2—C6—O1	60.4 (2)
C2—C1—C3—O4	−57.4 (2)	C4—O2—C6—C7	179.00 (16)
C4—C1—C3—O4	−179.27 (15)	C5—O1—C6—O2	−60.02 (18)
C5—C1—C3—O4	62.89 (19)	C5—O1—C6—C7	−179.11 (14)
C6—O2—C4—C1	−57.7 (2)	O2—C6—C7—C8	173.00 (17)
C2—C1—C4—O2	170.43 (14)	O1—C6—C7—C8	−66.4 (2)
C3—C1—C4—O2	−67.93 (19)	C6—C7—C8—C9	178.94 (17)
C5—C1—C4—O2	52.08 (19)	C7—C8—C9—C10	180.00 (18)
C6—O1—C5—C1	57.40 (18)	C8—C9—C10—C11	−176.53 (18)
C2—C1—C5—O1	−172.15 (14)	C9—C10—C11—C12	−178.08 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4i	0.84 (1)	1.86 (1)	2.664 (2)	162 (3)
O4—H4···O3ii	0.85 (1)	1.81 (1)	2.630 (2)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.84 (1)	1.86 (1)	2.664 (2)	162 (3)
O4—H4⋯O3ii	0.85 (1)	1.81 (1)	2.630 (2)	164 (3)

Symmetry codes: (i) ; (ii) .