Cyclo-hexane-1,2,3,4,5-pentol.

In the title compound, C(6)H(12)O(5), the cyclo-hexane ring adopts a chair conformation. The absolute configuration is not defined. However, the relative configuration can be assigned as 1R*,3R*,4S*,S*. In the crystal structure, mol-ecules are linked by strong inter-molecular O-H⋯O hydrogen bonds, producing a three-dimensional network.

Related literature

For details of the biological activity and applications of cyclohexane derivatives, see: Eddington et al. (2000 ▶); Padmavathi et al. (2000 ▶, 2001 ▶); Li & Strobel (2001 ▶). For puckering parameters and displacement asymmetric parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C6H12O5

M = 164.16

Monoclinic,

a = 6.4727 (5) Å

b = 8.4851 (6) Å

c = 6.8249 (5) Å

β = 110.796 (2)°

V = 350.41 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.977

5019 measured reflections

2418 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.06

2418 reflections

105 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 994 Friedel pairs

Flack parameter: 0.7 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014135/kp2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014135/kp2211Isup2.hkl

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

C6H12O5	F(000) = 176
Mr = 164.16	Dx = 1.556 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2418 reflections
a = 6.4727 (5) Å	θ = 3.2–33.3°
b = 8.4851 (6) Å	µ = 0.14 mm−1
c = 6.8249 (5) Å	T = 293 K
β = 110.796 (2)°	Block, colourless
V = 350.41 (5) Å3	0.21 × 0.19 × 0.17 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2418 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 33.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.972, Tmax = 0.977	k = −12→12
5019 measured reflections	l = −9→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0106P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2418 reflections	Δρmax = 0.39 e Å−3
105 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 994 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.7 (6)

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
C1	0.39464 (15)	0.00491 (11)	0.41069 (16)	0.01595 (17)
H1	0.4688	−0.0926	0.4757	0.019*
C2	0.15563 (14)	−0.03135 (11)	0.27557 (15)	0.01522 (17)
H2	0.0821	0.0694	0.2247	0.018*
C3	0.13572 (14)	−0.13189 (11)	0.08297 (15)	0.01626 (17)
H3	−0.0198	−0.1352	−0.0093	0.020*
C4	0.27248 (16)	−0.06837 (11)	−0.04069 (15)	0.01663 (17)
H4	0.2741	−0.1468	−0.1456	0.020*
C5	0.51009 (15)	−0.03378 (11)	0.10101 (16)	0.01768 (18)
H5A	0.5837	−0.1318	0.1590	0.021*
H5B	0.5889	0.0137	0.0188	0.021*
C6	0.51703 (15)	0.07685 (11)	0.27875 (16)	0.01628 (17)
H6	0.4414	0.1747	0.2168	0.020*
O1	0.73862 (11)	0.11569 (9)	0.40896 (14)	0.02328 (17)
H1A	0.8190	0.0392	0.4180	0.035*
O2	0.38759 (13)	0.11155 (10)	0.57023 (13)	0.02410 (17)
H2A	0.5140	0.1337	0.6464	0.036*
O3	0.04224 (12)	−0.10449 (9)	0.39647 (13)	0.02046 (16)
H3A	0.1094	−0.1839	0.4529	0.031*
O4	0.20891 (12)	−0.28909 (9)	0.14488 (13)	0.02034 (16)
H4A	0.1094	−0.3390	0.1642	0.031*
O5	0.16705 (13)	0.07199 (9)	−0.14612 (13)	0.02343 (17)
H5	0.2119	0.0922	−0.2416	0.035*

	U11	U22	U33	U12	U13	U23
C1	0.0173 (4)	0.0179 (4)	0.0146 (4)	−0.0003 (3)	0.0080 (3)	−0.0012 (3)
C2	0.0156 (3)	0.0175 (4)	0.0152 (4)	0.0008 (3)	0.0088 (3)	0.0005 (3)
C3	0.0166 (3)	0.0182 (4)	0.0147 (4)	0.0003 (3)	0.0065 (3)	−0.0001 (3)
C4	0.0192 (4)	0.0187 (4)	0.0136 (4)	0.0020 (3)	0.0078 (3)	0.0000 (3)
C5	0.0179 (4)	0.0215 (4)	0.0167 (4)	0.0012 (3)	0.0099 (3)	−0.0006 (3)
C6	0.0159 (3)	0.0180 (4)	0.0173 (4)	−0.0007 (3)	0.0088 (3)	−0.0006 (3)
O1	0.0168 (3)	0.0249 (3)	0.0288 (4)	−0.0031 (3)	0.0089 (3)	−0.0074 (3)
O2	0.0253 (3)	0.0310 (4)	0.0205 (4)	−0.0075 (3)	0.0136 (3)	−0.0112 (3)
O3	0.0215 (3)	0.0226 (3)	0.0233 (4)	0.0010 (3)	0.0155 (3)	0.0027 (3)
O4	0.0231 (3)	0.0162 (3)	0.0237 (4)	−0.0008 (2)	0.0107 (3)	0.0000 (3)
O5	0.0265 (3)	0.0278 (4)	0.0195 (4)	0.0093 (3)	0.0125 (3)	0.0094 (3)

C1—O2	1.4289 (13)	C4—H4	0.9800
C1—C6	1.5223 (14)	C5—C6	1.5218 (14)
C1—C2	1.5249 (12)	C5—H5A	0.9700
C1—H1	0.9800	C5—H5B	0.9700
C2—O3	1.4264 (12)	C6—O1	1.4319 (11)
C2—C3	1.5337 (14)	C6—H6	0.9800
C2—H2	0.9800	O1—H1A	0.8200
C3—O4	1.4282 (12)	O2—H2A	0.8200
C3—C4	1.5221 (14)	O3—H3A	0.8200
C3—H3	0.9800	O4—H4A	0.8200
C4—O5	1.4328 (12)	O5—H5	0.8200
C4—C5	1.5266 (13)
O2—C1—C6	111.16 (8)	O5—C4—H4	108.9
O2—C1—C2	106.77 (7)	C3—C4—H4	108.9
C6—C1—C2	110.64 (8)	C5—C4—H4	108.9
O2—C1—H1	109.4	C6—C5—C4	111.20 (8)
C6—C1—H1	109.4	C6—C5—H5A	109.4
C2—C1—H1	109.4	C4—C5—H5A	109.4
O3—C2—C1	110.97 (8)	C6—C5—H5B	109.4
O3—C2—C3	110.48 (7)	C4—C5—H5B	109.4
C1—C2—C3	112.89 (7)	H5A—C5—H5B	108.0
O3—C2—H2	107.4	O1—C6—C5	112.10 (8)
C1—C2—H2	107.4	O1—C6—C1	110.01 (8)
C3—C2—H2	107.4	C5—C6—C1	110.48 (8)
O4—C3—C4	107.32 (8)	O1—C6—H6	108.0
O4—C3—C2	110.35 (8)	C5—C6—H6	108.0
C4—C3—C2	112.94 (7)	C1—C6—H6	108.0
O4—C3—H3	108.7	C6—O1—H1A	109.5
C4—C3—H3	108.7	C1—O2—H2A	109.5
C2—C3—H3	108.7	C2—O3—H3A	109.5
O5—C4—C3	107.80 (8)	C3—O4—H4A	109.5
O5—C4—C5	110.57 (8)	C4—O5—H5	109.5
C3—C4—C5	111.73 (8)
O2—C1—C2—O3	−61.20 (10)	O4—C3—C4—C5	−72.15 (10)
C6—C1—C2—O3	177.71 (7)	C2—C3—C4—C5	49.69 (10)
O2—C1—C2—C3	174.15 (8)	O5—C4—C5—C6	65.25 (11)
C6—C1—C2—C3	53.07 (10)	C3—C4—C5—C6	−54.82 (11)
O3—C2—C3—O4	−54.15 (10)	C4—C5—C6—O1	−177.75 (8)
C1—C2—C3—O4	70.77 (10)	C4—C5—C6—C1	59.17 (10)
O3—C2—C3—C4	−174.27 (7)	O2—C1—C6—O1	59.39 (10)
C1—C2—C3—C4	−49.35 (10)	C2—C1—C6—O1	177.84 (8)
O4—C3—C4—O5	166.16 (7)	O2—C1—C6—C5	−176.32 (7)
C2—C3—C4—O5	−71.99 (10)	C2—C1—C6—C5	−57.87 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.82	1.94	2.7347 (11)	164
O2—H2A···O4ii	0.82	1.96	2.7761 (12)	170
O3—H3A···O1iii	0.82	2.02	2.8417 (11)	177
O4—H4A···O5iv	0.82	1.91	2.7067 (12)	165
O5—H5···O2v	0.82	2.00	2.8036 (12)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.82	1.94	2.7347 (11)	164
O2—H2A⋯O4ii	0.82	1.96	2.7761 (12)	170
O3—H3A⋯O1iii	0.82	2.02	2.8417 (11)	177
O4—H4A⋯O5iv	0.82	1.91	2.7067 (12)	165
O5—H5⋯O2v	0.82	2.00	2.8036 (12)	166

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