2-[(1R*,4R*)-1,4-Dihy-droxy-cyclo-hex-yl]acetic acid.

The title compound, C(8)H(14)O(4), is an isolation product of the aerial parts of Senecio desfontanei. The acetic acid group is oriented at a dihedral angle of 48.03 (9)° with respect to the basal plane of the cyclo-hexane-1,4-diol chair. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring with an envelope conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, resulting in R(3) (3)(20) ring motifs and C(2) O-H⋯O-H⋯O-H⋯ chains. Overall, a three-dimensional polymeric network arises. A C-H⋯O contact is also present.

Related literature

For related structures, see: Jasinski et al. (2009 ▶); Vasudev et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H14O4

M = 174.19

Triclinic,

a = 5.7301 (4) Å

b = 6.3493 (3) Å

c = 6.4964 (4) Å

α = 92.863 (2)°

β = 97.223 (1)°

γ = 108.258 (2)°

V = 221.67 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.28 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.935, T max = 0.965

3664 measured reflections

1092 independent reflections

932 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.091

S = 1.07

1092 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010397/hb5819sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010397/hb5819Isup2.hkl

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

C8H14O4	Z = 1
Mr = 174.19	F(000) = 94
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7301 (4) Å	Cell parameters from 933 reflections
b = 6.3493 (3) Å	θ = 3.2–28.4°
c = 6.4964 (4) Å	µ = 0.10 mm−1
α = 92.863 (2)°	T = 296 K
β = 97.223 (1)°	Needle, colorless
γ = 108.258 (2)°	0.28 × 0.12 × 0.10 mm
V = 221.67 (2) Å3

Bruker Kappa APEXII CCD diffractometer	1092 independent reflections
Radiation source: fine-focus sealed tube	932 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 3.2°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.935, Tmax = 0.965	l = −8→8
3664 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.0008P] where P = (Fo2 + 2Fc2)/3
1092 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	−0.1847 (3)	0.0914 (3)	−0.1705 (3)	0.0440 (5)
O2	0.1853 (4)	0.0521 (4)	−0.1685 (4)	0.0773 (9)
O3	0.6317 (3)	0.6910 (3)	0.6378 (3)	0.0431 (5)
O4	0.5902 (3)	0.4332 (3)	−0.0313 (2)	0.0359 (5)
C1	0.0589 (4)	0.1643 (4)	−0.1287 (3)	0.0417 (7)
C2	0.1589 (4)	0.4007 (4)	−0.0290 (4)	0.0401 (7)
C3	0.4158 (4)	0.4631 (3)	0.1003 (3)	0.0304 (6)
C4	0.4181 (4)	0.3231 (3)	0.2851 (3)	0.0382 (7)
C5	0.6749 (5)	0.3888 (4)	0.4164 (4)	0.0414 (7)
C6	0.7759 (4)	0.6356 (4)	0.4899 (3)	0.0391 (7)
C7	0.7640 (4)	0.7782 (4)	0.3096 (4)	0.0379 (7)
C8	0.5067 (4)	0.7087 (3)	0.1812 (3)	0.0341 (7)
H1	−0.238 (5)	−0.036 (5)	−0.231 (5)	0.0528*
H2A	0.04354	0.42391	0.05989	0.0481*
H2B	0.16539	0.50069	−0.13778	0.0481*
H3	0.627 (5)	0.610 (5)	0.740 (5)	0.0517*
H4	0.556 (5)	0.301 (5)	−0.077 (4)	0.0430*
H4A	0.29895	0.34223	0.37184	0.0458*
H4B	0.36752	0.16699	0.23368	0.0458*
H5A	0.66520	0.30369	0.53680	0.0497*
H5B	0.78917	0.35099	0.33472	0.0497*
H6	0.94896	0.67271	0.55625	0.0469*
H7A	0.80965	0.93295	0.36434	0.0455*
H7B	0.88352	0.76609	0.22023	0.0455*
H8A	0.51074	0.79800	0.06399	0.0409*
H8B	0.39057	0.73763	0.26622	0.0409*

	U11	U22	U33	U12	U13	U23
O1	0.0402 (9)	0.0388 (9)	0.0490 (10)	0.0100 (7)	0.0025 (7)	−0.0051 (7)
O2	0.0475 (11)	0.0688 (13)	0.1084 (19)	0.0249 (10)	−0.0090 (11)	−0.0466 (13)
O3	0.0573 (10)	0.0406 (9)	0.0293 (8)	0.0122 (7)	0.0094 (7)	0.0006 (7)
O4	0.0380 (8)	0.0414 (9)	0.0320 (8)	0.0167 (7)	0.0106 (6)	0.0001 (7)
C1	0.0380 (12)	0.0476 (12)	0.0379 (12)	0.0158 (10)	−0.0004 (9)	−0.0073 (10)
C2	0.0357 (11)	0.0408 (12)	0.0448 (13)	0.0158 (9)	0.0042 (10)	−0.0056 (10)
C3	0.0343 (10)	0.0324 (10)	0.0265 (10)	0.0126 (8)	0.0087 (8)	0.0002 (8)
C4	0.0492 (12)	0.0295 (10)	0.0346 (12)	0.0093 (9)	0.0103 (10)	0.0032 (9)
C5	0.0574 (14)	0.0424 (12)	0.0315 (12)	0.0253 (11)	0.0073 (10)	0.0079 (9)
C6	0.0381 (11)	0.0468 (13)	0.0322 (12)	0.0151 (10)	0.0025 (9)	0.0006 (9)
C7	0.0422 (12)	0.0336 (10)	0.0352 (12)	0.0069 (9)	0.0097 (9)	0.0024 (9)
C8	0.0412 (12)	0.0311 (10)	0.0322 (12)	0.0138 (9)	0.0076 (9)	0.0045 (9)

O1—C1	1.313 (3)	C6—C7	1.524 (3)
O2—C1	1.205 (3)	C7—C8	1.520 (3)
O3—C6	1.441 (3)	C2—H2A	0.9700
O4—C3	1.443 (3)	C2—H2B	0.9700
O1—H1	0.83 (3)	C4—H4A	0.9700
O3—H3	0.86 (3)	C4—H4B	0.9700
O4—H4	0.83 (3)	C5—H5A	0.9700
C1—C2	1.507 (3)	C5—H5B	0.9700
C2—C3	1.523 (3)	C6—H6	0.9800
C3—C8	1.523 (3)	C7—H7A	0.9700
C3—C4	1.530 (3)	C7—H7B	0.9700
C4—C5	1.527 (4)	C8—H8A	0.9700
C5—C6	1.519 (3)	C8—H8B	0.9700
C1—O1—H1	112 (2)	H2A—C2—H2B	108.00
C6—O3—H3	111 (2)	C3—C4—H4A	109.00
C3—O4—H4	112 (2)	C3—C4—H4B	109.00
O1—C1—O2	122.7 (2)	C5—C4—H4A	109.00
O1—C1—C2	112.7 (2)	C5—C4—H4B	109.00
O2—C1—C2	124.7 (2)	H4A—C4—H4B	108.00
C1—C2—C3	114.80 (19)	C4—C5—H5A	109.00
O4—C3—C8	106.40 (17)	C4—C5—H5B	109.00
O4—C3—C4	109.61 (17)	C6—C5—H5A	109.00
C4—C3—C8	109.02 (15)	C6—C5—H5B	109.00
C2—C3—C4	112.02 (18)	H5A—C5—H5B	108.00
C2—C3—C8	110.55 (18)	O3—C6—H6	109.00
O4—C3—C2	109.09 (17)	C5—C6—H6	109.00
C3—C4—C5	111.86 (18)	C7—C6—H6	109.00
C4—C5—C6	112.5 (2)	C6—C7—H7A	109.00
O3—C6—C7	107.08 (19)	C6—C7—H7B	109.00
O3—C6—C5	110.6 (2)	C8—C7—H7A	109.00
C5—C6—C7	111.52 (18)	C8—C7—H7B	109.00
C6—C7—C8	112.19 (19)	H7A—C7—H7B	108.00
C3—C8—C7	112.17 (18)	C3—C8—H8A	109.00
C1—C2—H2A	109.00	C3—C8—H8B	109.00
C1—C2—H2B	109.00	C7—C8—H8A	109.00
C3—C2—H2A	109.00	C7—C8—H8B	109.00
C3—C2—H2B	109.00	H8A—C8—H8B	108.00
O1—C1—C2—C3	156.30 (19)	C2—C3—C8—C7	−179.47 (19)
O2—C1—C2—C3	−24.2 (3)	C4—C3—C8—C7	57.0 (2)
C1—C2—C3—O4	59.4 (2)	C3—C4—C5—C6	54.8 (3)
C1—C2—C3—C4	−62.1 (2)	C4—C5—C6—O3	67.6 (2)
C1—C2—C3—C8	176.07 (18)	C4—C5—C6—C7	−51.4 (3)
O4—C3—C4—C5	59.7 (2)	O3—C6—C7—C8	−69.5 (2)
C2—C3—C4—C5	−179.04 (19)	C5—C6—C7—C8	51.6 (3)
C8—C3—C4—C5	−56.4 (2)	C6—C7—C8—C3	−55.6 (2)
O4—C3—C8—C7	−61.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.83 (3)	1.78 (3)	2.608 (3)	177 (3)
O3—H3···O4ii	0.86 (3)	1.90 (3)	2.756 (2)	175 (3)
O4—H4···O1iii	0.83 (3)	2.39 (3)	3.007 (3)	131 (3)
O4—H4···O2	0.83 (3)	2.20 (3)	2.789 (3)	128 (3)
C5—H5A···O1iv	0.97	2.60	3.511 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.83 (3)	1.78 (3)	2.608 (3)	177 (3)
O3—H3⋯O4ii	0.86 (3)	1.90 (3)	2.756 (2)	175 (3)
O4—H4⋯O1iii	0.83 (3)	2.39 (3)	3.007 (3)	131 (3)
O4—H4⋯O2	0.83 (3)	2.20 (3)	2.789 (3)	128 (3)
C5—H5A⋯O1iv	0.97	2.60	3.511 (3)	157

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