2,8-Dimethyl­tricyclo­[5.3.1.13,9]dodecane-syn-2,syn-8-diol–propanoic acid (1/1)

Mizobe, Y.; Bishop, R.; Craig, D.C.; Scudder, M.L.

doi:10.1107/S1600536809016547

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1241

doi:10.1107/S1600536809016547

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2,8-Dimethyltricyclo[5.3.1.1^3,9]dodecane-syn-2,syn-8-diol–propanoic acid (1/1)

Yuji Mizobe,^a ‡ Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 24 April 2009; accepted 4 May 2009; online 14 May 2009)

The racemic title compound, C₁₄H₂₄O₂·C₃H₆O₂, crystallizes in the monoclinic space group P2₁/c as a 1:1 diol/carboxylic acid cocrystal, A–B. The lattice incorporates infinite chains of the alcohol–carboxylic acid–alcohol supramolecular synthon, (⋯O—H⋯O=C(R)—O—H⋯O—H⋯), in which the hydrogen-bonded molecules (A—B—A)_n surround a pseudo-threefold screw axis. The carboxylic acid group functions like an extended alcohol hydroxy group. Each diol, A, takes part in two such threefold screw arrangements, leading to a hydrogen-bonded layer structure, with adjacent layers containing diol molecules of opposite handedness. The central C atom of the propano bridge is disordered over two sites of occupancies 0.75 (1) and 0.25 (1). The methyl group of the propanoic acid molecule is disordered over two sites of occupancies 0.68 (1) and 0.32 (1).

Related literature

For related literature on the diol component of the title compound, see: Bishop (2009 ); Dance et al. (1986 ). Two members of this diol family have been found previously to form such 1:1 compounds with carboxylic acids, see: Alshahateet et al. (2004 ); Yue et al. (2006 ).

Experimental

Crystal data

C₁₄H₂₄O₂·C₃H₆O₂
M_r = 298.4
Monoclinic, P 2₁ /c
a = 7.390 (4) Å
b = 13.218 (5) Å
c = 18.469 (8) Å
β = 110.23 (2)°
V = 1693 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.10 mm (radius)

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3188 measured reflections
2942 independent reflections
1786 reflections with I > 2σ(I)
R_int = 0.014
1 standard reflections frequency: 30 min intensity decay: 29%

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.070
S = 1.32
2942 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O2Pⁱ	1.00	1.82	2.822 (3)	180
O2—H102⋯O1ⁱⁱ	1.00	1.75	2.746 (3)	180
O1P—H101P⋯O2	1.00	1.64	2.635 (3)	180
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: RAELS (Rae, 2000 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CrystalMaker (Palmer, 2005 ); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016547/hg2504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016547/hg2504Isup2.hkl

checkCIF report

Comment top

The diol component, A, of the title compound, A—B, is a member of the helical tubuland host family, a major characteristic of which is formation of lattice inclusion compounds in the chiral space group P3₁21 (or its enantiomorph P3₂21) (Bishop, 2009). A forms this structure when crystallized from non-protic solvents (Dance et al., 1986). Some, but by no means all, of this family of diols can also form hydrogen-bonded co-crystals when crystallized from protic solvents. Two members of this diol family have been found previously to form such 1:1 compounds with carboxylic acids (Alshahateet et al., 2004; Yue et al., 2006). These co-crystals utilize infinite chains of an alcohol–carboxylic acid–alcohol supramolecular sython, (···O—H···O═ C(R)—O—H···O—H···), in which the carboxylic acid group behaves as if it were an extended alcohol hydroxy group. The diol, A, in the title compound is now found to be the third helical tubuland diol to behave in this manner (Fig. 1). Its 1:1 co-crystals with propanoic acid, A—B, contain chains of hydrogen-bonded molecules (A—B—A-)_n surrounding pseudo-threefold screw axes resulting in formation of chiral layers as each diol, A, hydrogen bonds within two such threefold screw arrangements (Figs. 2 and 3). Adjacent layers contain diol molecules with the opposite handedness. The resultant lattice is essentially isostructural with the previous examples in P2₁/c found to use this novel supramolecular synthon.

Related literature top

For related literature on the diol component of the title compound, see: Bishop (2009); Dance et al. (1986). Two members of this diol family have been found previously to form such 1:1 compounds with carboxylic acids, see: Alshahateet et al. (2004); Yue et al. (2006).

Experimental top

Racemic 2,8-dimethyltricyclo[5.3.1.1^3,9]dodecane-syn-2,syn-8-diol was prepared as described (Dance et al., 1986) and the X-ray quality co-crystals obtained by slow concentration of a propanoic acid solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Softwar (Enraf–Nonius, 1989); data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997) and CrystalMaker (Palmer, 2005); software used to prepare material for publication: local programs.

Figures top

	Fig. 1. Molecular structure of the A and B components of the title compound, with ellipsoids drawn at the 30% probability level.
	Fig. 2. One layer of the structure showing the intermolecular hydrogen bonding linking A and B molecules in chains. C atoms of the propanoic acid are coloured pink.
	Fig. 3. The orthogonal view showing the pseudo 3₁ symmetric nature of the arrangement in two adjacent layers. C atoms of the propanoic acid are coloured pink.

2,8-Dimethyltricyclo[5.3.1.1^3,9]dodecane-syn-2,syn-8-diol– propanoic acid (1/1) top

Crystal data top

C₁₄H₂₄O₂·C₃H₆O₂	F(000) = 656.0
M_r = 298.4	D_x = 1.17 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.390 (4) Å	Cell parameters from 11 reflections
b = 13.218 (5) Å	θ = 11–12°
c = 18.469 (8) Å	µ = 0.08 mm⁻¹
β = 110.23 (2)°	T = 294 K
V = 1693 (1) Å³	Irregular, colourless
Z = 4	0.10 mm (radius)

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 25°
ω/2θ scans	h = 0→8
3188 measured reflections	k = 0→15
2942 independent reflections	l = −22→22
1786 reflections with I > 2σ(I)	1 standard reflections every 30 min
R_int = 0.014	intensity decay: 29%

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F) + 0.0004F²]
S = 1.32	(Δ/σ)_max = 0.003
2942 reflections	Δρ_max = 0.39 e Å⁻³
199 parameters	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₂₄O₂·C₃H₆O₂	V = 1693 (1) Å³
M_r = 298.4	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.390 (4) Å	µ = 0.08 mm⁻¹
b = 13.218 (5) Å	T = 294 K
c = 18.469 (8) Å	0.10 mm (radius)
β = 110.23 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.014
3188 measured reflections	1 standard reflections every 30 min
2942 independent reflections	intensity decay: 29%
1786 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.32	Δρ_max = 0.39 e Å⁻³
2942 reflections	Δρ_min = −0.41 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.7617 (2)	0.2866 (1)	0.2685 (1)	0.0659 (5)
O2	0.4331 (2)	0.66382 (11)	0.16336 (9)	0.0559 (5)
C1	0.4896 (3)	0.3428 (2)	0.1636 (1)	0.0495 (6)
C2	0.7107 (3)	0.3385 (2)	0.1951 (1)	0.0496 (6)
C3	0.8088 (3)	0.4441 (2)	0.2035 (1)	0.0513 (6)
C4	0.6996 (3)	0.5155 (2)	0.1356 (1)	0.0503 (6)
C5	0.4789 (3)	0.5105 (2)	0.1032 (1)	0.0475 (6)
C6	0.3662 (3)	0.5599 (2)	0.1493 (1)	0.0472 (6)
C7	0.3899 (3)	0.5039 (2)	0.2262 (1)	0.0528 (6)
C8	0.3898 (4)	0.3878 (2)	0.2161 (1)	0.0579 (7)
C9	0.4195 (3)	0.4001 (2)	0.0871 (1)	0.0536 (6)
C10	0.7824 (4)	0.2728 (2)	0.1425 (2)	0.0718 (8)
C11	0.1519 (4)	0.5658 (2)	0.1009 (2)	0.0656 (8)
C12	0.8701 (4)	0.4943 (2)	0.2831 (2)	0.0695 (8)
C13	0.7455 (5)	0.5768 (3)	0.2979 (2)	0.067 (1)	0.75
C13'	0.7388 (9)	0.4872 (7)	0.3304 (4)	0.067 (1)	0.25
C14	0.5481 (5)	0.5443 (2)	0.2994 (1)	0.0707 (8)
O1P	0.5377 (3)	0.7775 (1)	0.0674 (1)	0.0740 (6)
O2P	0.8391 (3)	0.7734 (2)	0.1482 (1)	0.0801 (6)
C1P	0.7228 (4)	0.7995 (2)	0.0878 (2)	0.0667 (7)
C2P	0.7710 (5)	0.8619 (3)	0.0287 (2)	0.096 (1)
C3P	0.9587 (9)	0.8359 (5)	0.0180 (3)	0.119 (2)	0.68
C3'P	0.6746 (18)	0.9630 (8)	0.0220 (6)	0.119 (2)	0.32
H101	0.9031	0.2819	0.2980	0.066
H102	0.3622	0.7085	0.1882	0.056
HC1	0.4427	0.2716	0.1523	0.049
HC3	0.9335	0.4301	0.1955	0.051
H1C4	0.7466	0.5001	0.0921	0.050
H2C4	0.7357	0.5865	0.1536	0.050
HC5	0.4377	0.5454	0.0520	0.047
HC7	0.2666	0.5181	0.2354	0.053
H1C8	0.2520	0.3657	0.1953	0.058
H2C8	0.4535	0.3580	0.2686	0.058
H1C9	0.2759	0.3951	0.0636	0.054
H2C9	0.4795	0.3706	0.0509	0.054
H1C10	0.7499	0.3061	0.0909	0.072
H2C10	0.9254	0.2643	0.1660	0.072
H3C10	0.7188	0.2050	0.1360	0.072
H1C11	0.0979	0.4958	0.0894	0.066
H2C11	0.0820	0.6035	0.1301	0.066
H3C11	0.1354	0.6018	0.0514	0.066
H1C12	1.0007	0.5242	0.2929	0.069	0.75
H2C12	0.8794	0.4394	0.3215	0.069	0.75
H1'C12	0.8886	0.5679	0.2752	0.069	0.25
H2'C12	0.9963	0.4635	0.3147	0.069	0.25
H1C13	0.7237	0.6289	0.2565	0.067	0.75
H2C13	0.8185	0.6079	0.3491	0.067	0.75
H1C13'	0.8114	0.5142	0.3831	0.067	0.25
H2C13'	0.7085	0.4141	0.3342	0.067	0.25
H1C14	0.5727	0.4897	0.3391	0.071	0.75
H2C14	0.4921	0.6047	0.3166	0.071	0.75
H1'C14	0.4920	0.5456	0.3415	0.071	0.25
H2'C14	0.5785	0.6150	0.2880	0.071	0.25
H101P	0.4980	0.7344	0.1038	0.074
H1C2P	0.7770	0.9345	0.0447	0.096	0.68
H2C2P	0.6649	0.8527	−0.0221	0.096	0.68
H1'C2P	0.7236	0.8267	−0.0224	0.096	0.32
H2'C2P	0.9138	0.8713	0.0452	0.096	0.32
H1C3P	0.9777	0.8811	−0.0222	0.119	0.68
H2C3P	1.0675	0.8456	0.0679	0.119	0.68
H3C3P	0.9554	0.7638	0.0011	0.119	0.68
H1C3P'	0.7056	1.0050	−0.0172	0.119	0.32
H2C3P'	0.5318	0.9533	0.0056	0.119	0.32
H3C3P'	0.7219	0.9979	0.0732	0.119	0.32

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.052 (1)	0.071 (1)	0.071 (1)	−0.0012 (9)	0.0151 (9)	0.0241 (9)
O2	0.060 (1)	0.046 (1)	0.068 (1)	−0.0018 (8)	0.0298 (8)	−0.0045 (8)
C1	0.049 (1)	0.041 (1)	0.059 (1)	−0.008 (1)	0.021 (1)	−0.002 (1)
C2	0.050 (1)	0.045 (1)	0.057 (1)	−0.001 (1)	0.022 (1)	0.003 (1)
C3	0.046 (1)	0.048 (1)	0.061 (2)	−0.002 (1)	0.020 (1)	0.000 (1)
C4	0.051 (1)	0.047 (1)	0.060 (2)	−0.002 (1)	0.028 (1)	0.000 (1)
C5	0.051 (1)	0.049 (1)	0.044 (1)	−0.003 (1)	0.019 (1)	0.001 (1)
C6	0.047 (1)	0.043 (1)	0.054 (1)	−0.003 (1)	0.020 (1)	−0.002 (1)
C7	0.053 (2)	0.058 (1)	0.056 (1)	0.003 (1)	0.030 (1)	0.005 (1)
C8	0.054 (2)	0.057 (2)	0.070 (2)	−0.002 (1)	0.031 (1)	0.007 (1)
C9	0.054 (2)	0.052 (1)	0.053 (2)	−0.003 (1)	0.016 (1)	−0.005 (1)
C10	0.067 (2)	0.058 (2)	0.099 (2)	0.005 (1)	0.039 (2)	−0.010 (2)
C11	0.047 (2)	0.070 (2)	0.074 (2)	0.002 (1)	0.014 (1)	0.004 (1)
C12	0.059 (2)	0.067 (2)	0.068 (2)	0.000 (1)	0.003 (1)	−0.008 (1)
C13	0.069 (2)	0.068 (2)	0.055 (2)	−0.005 (2)	0.008 (2)	−0.015 (2)
C13'	0.069 (2)	0.068 (2)	0.055 (2)	−0.005 (2)	0.008 (2)	−0.015 (2)
C14	0.087 (2)	0.077 (2)	0.049 (2)	0.002 (2)	0.025 (1)	−0.008 (1)
O1P	0.068 (1)	0.083 (1)	0.066 (1)	−0.010 (1)	0.0154 (9)	0.008 (1)
O2P	0.067 (1)	0.087 (1)	0.074 (1)	−0.013 (1)	0.008 (1)	0.011 (1)
C1P	0.073 (2)	0.058 (2)	0.067 (2)	−0.012 (2)	0.022 (2)	−0.002 (1)
C2P	0.105 (3)	0.099 (3)	0.084 (2)	−0.020 (2)	0.031 (2)	0.017 (2)
C3P	0.136 (5)	0.143 (5)	0.083 (3)	−0.002 (4)	0.046 (3)	0.024 (3)
C3'P	0.136 (5)	0.143 (5)	0.083 (3)	−0.002 (4)	0.046 (3)	0.024 (3)

Geometric parameters (Å, º) top

O1—C2	1.448 (3)	C11—H2C11	1.000
O1—H101	1.000	C11—H3C11	1.000
O2—C6	1.453 (3)	C12—C13	1.512 (4)
O2—H102	1.000	C12—C13'	1.516 (5)
C1—C2	1.535 (3)	C12—H1C12	1.000
C1—C8	1.527 (3)	C12—H2C12	1.000
C1—C9	1.527 (3)	C12—H1'C12	1.000
C1—HC1	1.000	C12—H2'C12	1.000
C2—C3	1.555 (3)	C13—C14	1.531 (4)
C2—C10	1.528 (3)	C13—H1C13	1.000
C3—C4	1.555 (3)	C13—H2C13	1.000
C3—C12	1.532 (3)	C13'—C14	1.525 (5)
C3—HC3	1.000	C13'—H1C13'	1.000
C4—C5	1.532 (3)	C13'—H2C13'	1.000
C4—H1C4	1.000	C14—H1C14	1.000
C4—H2C4	1.000	C14—H2C14	1.000
C5—C6	1.529 (3)	O1P—C1P	1.319 (3)
C5—C9	1.524 (3)	O1P—H101P	1.000
C5—HC5	1.000	O2P—C1P	1.199 (3)
C6—C7	1.556 (3)	C1P—C2P	1.506 (4)
C6—C11	1.528 (3)	C2P—C3P	1.507 (6)
C7—C8	1.547 (3)	C2P—C3'P	1.499 (8)
C7—C14	1.545 (4)	C2P—H1C2P	1.000
C7—HC7	1.000	C2P—H2C2P	1.000
C8—H1C8	1.000	C2P—H1'C2P	1.000
C8—H2C8	1.000	C2P—H2'C2P	1.000
C9—H1C9	1.000	C3P—H1C3P	1.000
C9—H2C9	1.000	C3P—H2C3P	1.000
C10—H1C10	1.000	C3P—H3C3P	1.000
C10—H2C10	1.000	C3'P—H1C3P'	1.000
C10—H3C10	1.000	C3'P—H2C3P'	1.000
C11—H1C11	1.000	C3'P—H3C3P'	1.000

C2—O1—H101	115.1	C6—C11—H1C11	109.5
C6—O2—H102	116.1	C6—C11—H2C11	109.5
C2—C1—C8	117.3 (2)	C6—C11—H3C11	109.5
C2—C1—C9	110.2 (2)	H1C11—C11—H2C11	109.5
C2—C1—HC1	106.9	H1C11—C11—H3C11	109.5
C8—C1—C9	108.1 (2)	H2C11—C11—H3C11	109.5
C8—C1—HC1	106.9	C3—C12—C13	119.4 (2)
C9—C1—HC1	106.9	C3—C12—C13'	119.4 (4)
O1—C2—C1	105.7 (2)	C3—C12—H1C12	106.9
O1—C2—C3	111.7 (2)	C3—C12—H2C12	106.9
O1—C2—C10	106.9 (2)	C3—C12—H1'C12	106.9
C1—C2—C3	113.8 (2)	C3—C12—H2'C12	106.9
C1—C2—C10	109.8 (2)	C13—C12—H1C12	106.9
C3—C2—C10	108.8 (2)	C13—C12—H2C12	106.9
C2—C3—C4	111.7 (2)	C13'—C12—H1'C12	106.9
C2—C3—C12	117.2 (2)	C13'—C12—H2'C12	106.9
C2—C3—HC3	103.9	H1C12—C12—H2C12	109.5
C4—C3—C12	114.2 (2)	H1'C12—C12—H2'C12	109.5
C4—C3—HC3	103.9	C12—C13—C14	116.4 (3)
C12—C3—HC3	103.9	C12—C13—H1C13	107.7
C3—C4—C5	118.3 (2)	C12—C13—H2C13	107.7
C3—C4—H1C4	107.2	C14—C13—H1C13	107.7
C3—C4—H2C4	107.2	C14—C13—H2C13	107.7
C5—C4—H1C4	107.2	H1C13—C13—H2C13	109.5
C5—C4—H2C4	107.2	C12—C13'—C14	116.5 (4)
H1C4—C4—H2C4	109.5	C12—C13'—H1C13'	107.7
C4—C5—C6	118.4 (2)	C12—C13'—H2C13'	107.7
C4—C5—C9	108.3 (2)	C14—C13'—H1C13'	107.7
C4—C5—HC5	106.5	C14—C13'—H2C13'	107.7
C6—C5—C9	110.0 (2)	H1C13'—C13'—H2C13'	109.5
C6—C5—HC5	106.5	C7—C14—C13	121.3 (2)
C9—C5—HC5	106.5	C7—C14—C13'	118.6 (4)
O2—C6—C5	106.6 (2)	C7—C14—H1C14	106.4
O2—C6—C7	111.3 (2)	C7—C14—H2C14	106.4
O2—C6—C11	106.0 (2)	C13—C14—H1C14	106.4
C5—C6—C7	113.3 (2)	C13—C14—H2C14	106.4
C5—C6—C11	110.5 (2)	H1C14—C14—H2C14	109.5
C7—C6—C11	109.0 (2)	C1P—O1P—H101P	116.7
C6—C7—C8	111.5 (2)	O1P—C1P—O2P	122.8 (3)
C6—C7—C14	116.5 (2)	O1P—C1P—C2P	113.2 (3)
C6—C7—HC7	104.2	O2P—C1P—C2P	124.0 (3)
C8—C7—C14	114.6 (2)	C1P—C2P—C3P	115.4 (3)
C8—C7—HC7	104.2	C1P—C2P—C3'P	108.8 (5)
C14—C7—HC7	104.2	C1P—C2P—H1C2P	108.0
C1—C8—C7	118.9 (2)	C1P—C2P—H2C2P	108.0
C1—C8—H1C8	107.1	C1P—C2P—H1'C2P	109.6
C1—C8—H2C8	107.1	C1P—C2P—H2'C2P	109.6
C7—C8—H1C8	107.1	H1C2P—C2P—H2C2P	109.5
C7—C8—H2C8	107.1	H1'C2P—C2P—H2'C2P	109.5
H1C8—C8—H2C8	109.5	C2P—C3P—H1C3P	109.5
C1—C9—C5	108.2 (2)	C2P—C3P—H2C3P	109.5
C1—C9—H1C9	109.8	C2P—C3P—H3C3P	109.5
C1—C9—H2C9	109.8	H1C3P—C3P—H2C3P	109.5
C5—C9—H1C9	109.8	H1C3P—C3P—H3C3P	109.5
C5—C9—H2C9	109.8	H2C3P—C3P—H3C3P	109.5
H1C9—C9—H2C9	109.5	C2P—C3'P—H1C3P'	109.5
C2—C10—H1C10	109.5	C2P—C3'P—H2C3P'	109.5
C2—C10—H2C10	109.5	C2P—C3'P—H3C3P'	109.5
C2—C10—H3C10	109.5	H1C3P'—C3'P—H2C3P'	109.5
H1C10—C10—H2C10	109.5	H1C3P'—C3'P—H3C3P'	109.5
H1C10—C10—H3C10	109.5	H2C3P'—C3'P—H3C3P'	109.5
H2C10—C10—H3C10	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2Pⁱ	1.00	1.82	2.822 (3)	180
O2—H102···O1ⁱⁱ	1.00	1.75	2.746 (3)	180
O1P—H101P···O2	1.00	1.64	2.635 (3)	180

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₄O₂·C₃H₆O₂
M_r	298.4
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.390 (4), 13.218 (5), 18.469 (8)
β (°)	110.23 (2)
V (Å³)	1693 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.10 (radius)

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3188, 2942, 1786
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.070, 1.32
No. of reflections	2942
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.41

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Softwar (Enraf–Nonius, 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEP-3 (Farrugia, 1997) and CrystalMaker (Palmer, 2005), local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2Pⁱ	1.00	1.82	2.822 (3)	180
O2—H102···O1ⁱⁱ	1.00	1.75	2.746 (3)	180
O1P—H101P···O2	1.00	1.64	2.635 (3)	180

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Footnotes

‡On leave from the Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

Acknowledgements

This research was supported by the Australian Research Council.

References

Alshahateet, S. F., Nakano, K., Bishop, R., Craig, D. C., Harris, K. D. M. & Scudder, M. L. (2004). CrystEngComm, 6, 5–10. Web of Science CSD CrossRef Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bishop, R. (2009). Acc. Chem. Res. 42, 67–78. Web of Science CrossRef PubMed CAS Google Scholar
Dance, I. G., Bishop, R., Hawkins, S. C., Lipari, T., Scudder, M. L. & Craig, D. C. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 1299–1307. CSD CrossRef Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Palmer, D. (2005). CrystalMaker. CrystalMaker Software Ltd, Yarnton, Oxfordshire, England. htttp://www.CrystalMaker.co.uk. Google Scholar
Rae, A. D. (2000). RAELS. Australian National University, Canberra. Google Scholar
Yue, W., Nakano, K., Bishop, R., Craig, D. C., Harris, K. D. M. & Scudder, M. L. (2006). CrystEngComm, 8, 250–256. Web of Science CSD CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,8-Di­methyl­tri­cyclo­[5.3.1.13,9]do­decane-syn-2,syn-8-diol–propanoic acid (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2,8-Dimethyltricyclo[5.3.1.1^3,9]dodecane-syn-2,syn-8-diol–propanoic acid (1/1)