(2-tert-Butyl-5-hy­droxy­methyl-1,3-dioxan-5-yl)methanol

Vargas, B.; Olivas, A.; Aguirre, G.; Madrigal, D.

doi:10.1107/S160053681202541X

Volume 68
Part 7
Page o2049
July 2012

Received 26 May 2012
Accepted 4 June 2012
Online 13 June 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.054
wR = 0.193
Data-to-parameter ratio = 25.9
Details

(2-tert-Butyl-5-hydroxymethyl-1,3-dioxan-5-yl)methanol

Berenice Vargas,^a Amelia Olivas,^b Gerardo Aguirre ^a and Domingo Madrigal ^a ^*

^aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico, and ^bCentro de Ciencias de la Materia Condensada, Universidad Nacional Autónoma de, México. Km. 107 Carretera Tijuana-Ensenada, Ensenada, BC, CP 22800, Mexico
Correspondence e-mail: madrigal@tectijuana.mx

In the title compound, C₁₀H₂₀O₄, 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, molecules are connected by O-HO hydrogen-bonds into zigzag chains of R⁴₄(8) and R²₂(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_r = 204.26
Triclinic, $[P \overline 1]$
a = 5.8337 (10) Å
b = 6.1408 (9) Å
c = 17.941 (3) Å
= 81.468 (12)°
= 87.335 (14)°
= 62.606 (13)°
V = 564.16 (15) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.013
3 standard reflections every 97 reflections intensity decay: 5.8%

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.193
S = 1.42
3283 reflections
127 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO4ⁱ	0.82	1.94	2.7346 (14)	162
O4-H4AO3ⁱⁱ	0.82	1.91	2.6878 (15)	159
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y, z.

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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2419 ).

Acknowledgements

Support for this work from the Dirección General de Educación Superior Tecnológica (DGEST) Grant 2574.09P, is gratefully acknowledged.

References

Anderson, J. E. (1967). J. Chem. Soc. B pp. 712-716.
Bailey, W. F., Connon, H., Eliel, E. L. & Wiberg, K. B. (1978). J. Am. Chem. Soc. 100, 2202-2209.
Juaristi, E., Gordillo, B., Martinez, R. & Toscano, R. A. (1989). J. Org. Chem. 54, 5963-5967.
Juaristi, E., Martinez, R., Mendez, R., Toscano, R. A., Soriano-Garcia, M., Eliel, E. L., Petsom, A. & Glass, R. S. (1987). J. Org. Chem. 52, 3806-3811.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). XSCANS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Vázquez-Hernández, M., Rosquete-Pina, G. A. & Juaristi, E. (2004). J. Org. Chem. 69, 9063-9072.
Zhang, M., Yuan, X.-Y. & Ng, S. W. (2010). Acta Cryst. E66, o2917.

organic compounds