2,6-Anhydro-1,3-di-O-benzyl-d-mannitol

Siqueira, E.C. de; Doboszewski, B.; McGarrah, J.; Nazarenko, A.Y.

doi:10.1107/S1600536811022306

Volume 67
Part 7
Pages o1653-o1654
July 2011

Received 5 June 2011
Accepted 8 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
R = 0.035
wR = 0.082
Data-to-parameter ratio = 7.4
Details

2,6-Anhydro-1,3-di-O-benzyl-D-mannitol

Edmilson Clarindo de Siqueira,^a Bogdan Doboszewski,^a James McGarrah ^b and Alexander Y. Nazarenko ^c ^*

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, 52171-900 Recife, PE, Brazil,^bDepartment of Chemistry, State University of New York, College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA, and ^cChemistry Department, State University of New York, College at Buffalo, 1300 Elmwood Avenue, Buffalo, NY 14222-1095, USA
Correspondence e-mail: nazareay@buffalostate.edu

In the title compound, C₂₀H₂₄O₅, the six-membered pyranose ring adopts a chair conformation. The dihedral angle between the planes of the phenyl groups of the benzyl substituents is 63.1°. Two types of intermolecular O-HO hydrogen bonds lead to the formation of infinite chains along the b axis. Only weak C-HO contacts exist between neighboring chains.

Related literature

For syntheses of this and similar compounds, see: Barker (1970); Doboszewski (1997, 2009); Doboszewski & de Siqueria (2010); Hartman (1970a,b). For related structures, see: Boeyens et al. (1983); Doboszewski & Nazarenko (2003); Guiry et al. (2008); Hong et al. (2005); Vidra et al. (1982). For conformations of six-membered rings, see: Schwarz (1973); Cremer & Pople (1975); Boeyens & Dobson (1987). For hydrogen bonding in carbohydrate chemistry, see Gilli & Gilli (2009); Desiraju & Steiner (1999); Jeffrey (1997), and references therein.

Experimental

Crystal data

C₂₀H₂₄O₅
M_r = 344.39
Monoclinic, P 2₁
a = 5.6584 (10) Å
b = 7.9610 (12) Å
c = 19.808 (4) Å
= 91.968 (6)°
V = 891.8 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 200 K
0.6 × 0.4 × 0.05 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) T_min = 0.91, T_max = 0.98
8624 measured reflections
1695 independent reflections
1458 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.082
S = 0.99
1695 reflections
228 parameters
1 restraint
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4O5ⁱ	0.84	1.95	2.789 (2)	175
O5-H5O2ⁱ	0.84	1.98	2.812 (2)	169
C6-H6BO5ⁱⁱ	0.99	2.54	3.461 (3)	155
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z.

Data collection: GIS (Bruker, 2010); cell refinement: APEX2 (Bruker, 2010) and SAINT (Bruker, 2009); data reduction: SAINT and XPREP in SHELXTL (Sheldrick, 2008a); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2379 ).

Acknowledgements

This study was supported by a grant for the X-ray diffractometer and by SUNY grant No. 1073053. AYN thanks Dr Bruce Noll (Bruker AXS) for useful advice in operating the X2S diffractometer, and Dr David Geiger (SUNY Geneseo) for help with the experiment.

References

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organic compounds