2-De-oxy-α-d-arabino-hexopyran-ose.

The title compound, C(6)H(12)O(5), is the α-pyran-ose form of the reducing aldose 2-de-oxy-d-arabino-hexose. The six-membered pyran-ose ring adopts a (4)C(1) conformation, with the anomeric hy-droxy group in axial and the other substituents in equatorial positions. In the crystal, each of the four hy-droxy groups acts as an inter-molecular hydrogen-bond donor function, resulting in a three-dimensional hydrogen-bonded network.

Related literature

For the crystal structure of 2-de­oxy-β-d-arabino-hexopyran­ose, see: Maluszynska et al. (1981 ▶) and for the crystal structures of α-d-glucose and α-d-mannose, see Brown et al. (1965 ▶) and Longchambon et al. (1976 ▶), respectively. For puckering parameters, see: Cremer & Pople (1975 ▶). Crystals of the title compound were obtained during the course of attemps to grow crystals of a phenyl­boronic acid ester of 2-de­oxy-d-arabino-hexose, see: Hess & Klüfers (2011 ▶).

Experimental

Crystal data

C6H12O5

M = 164.16

Orthorhombic,

a = 4.8538 (2) Å

b = 9.5323 (4) Å

c = 15.6718 (6) Å

V = 725.12 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 200 K

0.21 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

5622 measured reflections

1001 independent reflections

937 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.14

1001 reflections

104 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035264/kj2184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035264/kj2184Isup2.hkl

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

C6H12O5	F(000) = 352
Mr = 164.16	Dx = 1.504 (1) Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2672 reflections
a = 4.8538 (2) Å	θ = 3.1–27.5°
b = 9.5323 (4) Å	µ = 0.13 mm−1
c = 15.6718 (6) Å	T = 200 K
V = 725.12 (5) Å3	Rod, colourless
Z = 4	0.21 × 0.06 × 0.05 mm

Nonius KappaCCD diffractometer	937 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.030
MONTEL, graded multilayered X-ray optics	θmax = 27.5°, θmin = 3.4°
CCD; rotation images; thick slices scans	h = −6→6
5622 measured reflections	k = −12→12
1001 independent reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.298P] where P = (Fo2 + 2Fc2)/3
1001 reflections	(Δ/σ)max < 0.001
104 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	−0.0906 (4)	0.75609 (18)	0.88687 (10)	0.0296 (4)
H81	−0.1430	0.8030	0.9292	0.044*
O3	0.3063 (4)	0.45829 (17)	0.72256 (9)	0.0308 (4)
H83	0.2179	0.3892	0.7036	0.046*
O4	0.0700 (4)	0.28748 (16)	0.85187 (10)	0.0292 (4)
H84	0.1642	0.2202	0.8705	0.044*
O5	0.2069 (4)	0.61635 (15)	0.96649 (9)	0.0251 (4)
O6	−0.0846 (4)	0.42652 (18)	1.09339 (9)	0.0305 (4)
H86	−0.0049	0.4550	1.1377	0.046*
C1	0.1847 (6)	0.7158 (2)	0.89833 (14)	0.0259 (5)
H1	0.2957	0.8008	0.9132	0.031*
C2	0.2911 (5)	0.6559 (2)	0.81511 (13)	0.0248 (5)
H2A	0.2463	0.7213	0.7681	0.030*
H2B	0.4941	0.6473	0.8182	0.030*
C3	0.1683 (5)	0.5136 (2)	0.79562 (12)	0.0229 (5)
H3	−0.0325	0.5243	0.7828	0.027*
C4	0.2049 (5)	0.4156 (2)	0.87086 (12)	0.0219 (4)
H4	0.4055	0.3980	0.8806	0.026*
C5	0.0780 (5)	0.4826 (2)	0.95053 (12)	0.0219 (4)
H5	−0.1235	0.4975	0.9406	0.026*
C6	0.1161 (5)	0.3944 (2)	1.02968 (13)	0.0263 (5)
H6A	0.1017	0.2939	1.0143	0.032*
H6B	0.3026	0.4108	1.0532	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0353 (9)	0.0299 (8)	0.0238 (7)	0.0080 (8)	0.0022 (7)	0.0000 (7)
O3	0.0436 (10)	0.0274 (8)	0.0214 (7)	−0.0055 (8)	0.0082 (8)	−0.0041 (6)
O4	0.0396 (9)	0.0213 (7)	0.0269 (8)	−0.0068 (8)	−0.0051 (8)	−0.0013 (6)
O5	0.0372 (9)	0.0192 (7)	0.0189 (6)	−0.0015 (7)	−0.0060 (7)	−0.0002 (6)
O6	0.0379 (9)	0.0340 (9)	0.0195 (7)	−0.0042 (8)	0.0005 (7)	−0.0010 (6)
C1	0.0346 (12)	0.0215 (10)	0.0216 (9)	0.0010 (10)	−0.0013 (10)	0.0013 (8)
C2	0.0297 (11)	0.0221 (10)	0.0226 (9)	−0.0003 (10)	0.0013 (10)	0.0023 (8)
C3	0.0261 (11)	0.0256 (10)	0.0170 (8)	0.0004 (10)	0.0017 (8)	−0.0003 (8)
C4	0.0261 (10)	0.0186 (10)	0.0211 (9)	−0.0016 (9)	−0.0034 (9)	−0.0015 (7)
C5	0.0265 (10)	0.0206 (9)	0.0186 (9)	−0.0012 (9)	−0.0049 (9)	0.0003 (7)
C6	0.0357 (12)	0.0239 (10)	0.0192 (9)	0.0020 (10)	−0.0017 (9)	0.0010 (8)

O1—C1	1.402 (3)	C2—C3	1.512 (3)
O1—H81	0.8400	C2—H2A	0.9900
O3—C3	1.428 (2)	C2—H2B	0.9900
O3—H83	0.8400	C3—C4	1.515 (3)
O4—C4	1.418 (3)	C3—H3	1.0000
O4—H84	0.8400	C4—C5	1.532 (3)
O5—C1	1.433 (3)	C4—H4	1.0000
O5—C5	1.442 (3)	C5—C6	1.510 (3)
O6—C6	1.428 (3)	C5—H5	1.0000
O6—H86	0.8400	C6—H6A	0.9900
C1—C2	1.515 (3)	C6—H6B	0.9900
C1—H1	1.0000
?···?	?
C1—O1—H81	109.5	C2—C3—H3	109.5
C3—O3—H83	109.5	C4—C3—H3	109.5
C4—O4—H84	109.5	O4—C4—C3	108.28 (16)
C1—O5—C5	115.04 (15)	O4—C4—C5	110.16 (18)
C6—O6—H86	109.5	C3—C4—C5	109.27 (17)
O1—C1—O5	110.39 (19)	O4—C4—H4	109.7
O1—C1—C2	108.54 (19)	C3—C4—H4	109.7
O5—C1—C2	111.50 (18)	C5—C4—H4	109.7
O1—C1—H1	108.8	O5—C5—C6	107.26 (16)
O5—C1—H1	108.8	O5—C5—C4	109.60 (18)
C2—C1—H1	108.8	C6—C5—C4	112.82 (17)
C3—C2—C1	112.20 (18)	O5—C5—H5	109.0
C3—C2—H2A	109.2	C6—C5—H5	109.0
C1—C2—H2A	109.2	C4—C5—H5	109.0
C3—C2—H2B	109.2	O6—C6—C5	111.79 (18)
C1—C2—H2B	109.2	O6—C6—H6A	109.3
H2A—C2—H2B	107.9	C5—C6—H6A	109.3
O3—C3—C2	107.95 (17)	O6—C6—H6B	109.3
O3—C3—C4	109.96 (17)	C5—C6—H6B	109.3
C2—C3—C4	110.45 (16)	H6A—C6—H6B	107.9
O3—C3—H3	109.5
C5—O5—C1—O1	66.3 (2)	C2—C3—C4—C5	56.0 (2)
C5—O5—C1—C2	−54.4 (3)	C1—O5—C5—C6	−178.49 (18)
O1—C1—C2—C3	−71.6 (2)	C1—O5—C5—C4	58.7 (2)
O5—C1—C2—C3	50.2 (3)	O4—C4—C5—O5	−176.95 (16)
C1—C2—C3—O3	−172.65 (19)	C3—C4—C5—O5	−58.1 (2)
C1—C2—C3—C4	−52.4 (2)	O4—C4—C5—C6	63.6 (2)
O3—C3—C4—O4	−65.0 (2)	C3—C4—C5—C6	−177.56 (19)
C2—C3—C4—O4	175.95 (18)	O5—C5—C6—O6	81.9 (2)
O3—C3—C4—C5	174.99 (18)	C4—C5—C6—O6	−157.32 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H81···O5i	0.84	1.95	2.780 (2)	171.
O3—H83···O1ii	0.84	2.00	2.784 (2)	155.
O4—H84···O6iii	0.84	1.94	2.776 (3)	174.
O6—H86···O3iv	0.84	1.84	2.670 (2)	170.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H81⋯O5i	0.84	1.95	2.780 (2)	171
O3—H83⋯O1ii	0.84	2.00	2.784 (2)	155
O4—H84⋯O6iii	0.84	1.94	2.776 (3)	174
O6—H86⋯O3iv	0.84	1.84	2.670 (2)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .