3-Hydroxy­adamantane-1-acetic acid

Geng, X.-H.; Kong, L.-C.; Feng, Y.-L.

doi:10.1107/S1600536808020515

organic compounds

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Volume 64| Part 9| September 2008| Page o1716

doi:10.1107/S1600536808020515

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3-Hydroxyadamantane-1-acetic acid

Xiao-Hong Geng,^a Li-Chun Kong ^a and Yun-Long Feng ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky37@zjnu.cn

(Received 28 May 2008; accepted 3 July 2008; online 6 August 2008)

The crystal structure of the title adamantane derivative, C₁₂H₁₈O₃, has been determined by X-ray diffraction. The structure is stabilized by intermolecular O—H⋯O hydrogen bonds, forming a chain.

Related literature

For related literature, see: Lu & Yang (1996 ); Tukada & Mochizuki (2005 ); Zhao et al. (2003 ).

Experimental

Crystal data

C₁₂H₁₈O₃
M_r = 210.26
Triclinic, $[P \overline 1]$
a = 6.5120 (9) Å
b = 7.9485 (11) Å
c = 11.5469 (15) Å
α = 106.919 (10)°
β = 94.838 (10)°
γ = 104.443 (7)°
V = 545.73 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.30 × 0.13 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.98, T_max = 0.99
8786 measured reflections
2488 independent reflections
1574 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.03
2488 reflections
142 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.815 (15)	1.995 (16)	2.7959 (18)	168 (2)
O2—H2⋯O1ⁱⁱ	0.850 (16)	1.811 (16)	2.649 (2)	168 (2)
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020515/at2572sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020515/at2572Isup2.hkl

checkCIF report

Comment top

Adamantane and its derivatives have an extensive application in the field of medicine. For instance, adamantaneamine has an obvious effect on controlling the exuviating the influenza A virus and it can alleviate the Parkinson symptom (Lu et al., 1996). A large number of compounds containing amantadine have been synthesized (Tukada & Mochizuki, 2005; Zhao et al., 2003). Here we report the synthesis and crystal structure of the title compound (I), illustrated in Fig. 1.

The title compound (I) is an adamantane derivative. Single-crystal X-ray diffraction analyses demonstrate that hydrogen bonding produces an extensive polymeric network since the hydroxyl group substituents are simultaneously hydrogen bonded to the OH of the carboxyl group on an adjacent molecule and the carbonyl group of a different neighbor forming a 12-membered ring as shown in Fig. 2. A 16-membered ring is formed by intermolecular hydrogen bonding between the carbonyl O and hydroxyl H atoms of two molecules. The alternating 12- and 16-membered rings make the compound to form a one-dimensional network.

Related literature top

For related literature, see: Lu & Yang (1996); Tukada & Mochizuki (2005); Zhao et al. (2003).

Experimental top

The 3-hydroxy-1-adamantaneacetic was obtained from Zhejiang Key Laboratory for Reactive Chemistry on Solid Surface. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of distilled water.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. A packing diagram for the title compound. The O—H···O interactions are depicted by dashed lines.

3-Hydroxyadamantane-1-acetic acid top

Crystal data top

C₁₂H₁₈O₃	Z = 2
M_r = 210.26	F(000) = 228
Triclinic, P1	D_x = 1.280 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5120 (9) Å	Cell parameters from 1598 reflections
b = 7.9485 (11) Å	θ = 1.9–27.5°
c = 11.5469 (15) Å	µ = 0.09 mm⁻¹
α = 106.919 (10)°	T = 296 K
β = 94.838 (10)°	Block, colourless
γ = 104.443 (7)°	0.30 × 0.13 × 0.10 mm
V = 545.73 (13) Å³

Data collection top

Bruker APEXII area-detector diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.98, T_max = 0.99	k = −10→10
8786 measured reflections	l = −15→15

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.052P)² + 0.1083P] where P = (F_o² + 2F_c²)/3
2488 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₂H₁₈O₃	γ = 104.443 (7)°
M_r = 210.26	V = 545.73 (13) Å³
Triclinic, P1	Z = 2
a = 6.5120 (9) Å	Mo Kα radiation
b = 7.9485 (11) Å	µ = 0.09 mm⁻¹
c = 11.5469 (15) Å	T = 296 K
α = 106.919 (10)°	0.30 × 0.13 × 0.10 mm
β = 94.838 (10)°

Data collection top

Bruker APEXII area-detector diffractometer	2488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1574 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.99	R_int = 0.033
8786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
2488 reflections	Δρ_min = −0.17 e Å⁻³
142 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.0947 (2)	0.76522 (17)	0.09607 (12)	0.0581 (4)
H1	0.024 (3)	0.690 (3)	0.1232 (19)	0.070*
O2	0.5777 (2)	1.30404 (19)	0.01092 (13)	0.0620 (4)
H2	0.694 (3)	1.295 (3)	−0.015 (2)	0.074*
O3	0.7982 (2)	1.51594 (19)	0.17220 (13)	0.0647 (4)
C4	−0.0106 (3)	0.9805 (3)	0.26199 (16)	0.0462 (4)
H4B	−0.0679	0.8858	0.2976	0.055*
H4A	−0.1258	0.9836	0.2043	0.055*
C9	0.3516 (3)	0.9321 (2)	0.28586 (16)	0.0444 (4)
H9B	0.4665	0.9027	0.2431	0.053*
H9A	0.2979	0.8377	0.3223	0.053*
C3	0.1714 (3)	0.9376 (2)	0.19572 (15)	0.0392 (4)
C2	0.2580 (3)	1.0849 (2)	0.13783 (15)	0.0387 (4)
H2B	0.1441	1.0871	0.0790	0.046*
H2A	0.3724	1.0562	0.0943	0.046*
C8	0.5237 (3)	1.2664 (2)	0.32771 (15)	0.0413 (4)
H8B	0.5804	1.3850	0.3913	0.050*
H8A	0.6399	1.2391	0.2854	0.050*
C7	0.4377 (3)	1.1188 (2)	0.38625 (16)	0.0441 (4)
H7A	0.5541	1.1154	0.4444	0.053*
C6	0.2554 (3)	1.1612 (3)	0.45363 (16)	0.0494 (5)
H6B	0.2012	1.0676	0.4906	0.059*
H6A	0.3086	1.2787	0.5185	0.059*
C5	0.0756 (3)	1.1668 (2)	0.36319 (16)	0.0458 (5)
H5A	−0.0411	1.1949	0.4065	0.055*
C10	0.1616 (3)	1.3152 (2)	0.30564 (17)	0.0464 (5)
H10B	0.2146	1.4338	0.3694	0.056*
H10A	0.0462	1.3203	0.2491	0.056*
C1	0.3444 (3)	1.2738 (2)	0.23674 (14)	0.0352 (4)
C11	0.4224 (3)	1.4276 (2)	0.18016 (16)	0.0457 (5)
H11A	0.3065	1.4201	0.1186	0.055*
H11B	0.4522	1.5452	0.2441	0.055*
C12	0.6181 (3)	1.4222 (2)	0.12218 (16)	0.0436 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0652 (10)	0.0397 (7)	0.0542 (8)	−0.0080 (6)	0.0268 (7)	0.0076 (6)
O2	0.0614 (10)	0.0572 (9)	0.0552 (9)	0.0018 (7)	0.0240 (7)	0.0091 (7)
O3	0.0584 (10)	0.0567 (9)	0.0637 (9)	−0.0088 (7)	0.0151 (7)	0.0171 (7)
C4	0.0361 (10)	0.0536 (11)	0.0504 (11)	0.0072 (8)	0.0157 (8)	0.0217 (9)
C9	0.0466 (11)	0.0412 (10)	0.0567 (11)	0.0145 (8)	0.0201 (9)	0.0279 (8)
C3	0.0391 (10)	0.0350 (9)	0.0390 (9)	0.0028 (7)	0.0129 (7)	0.0099 (7)
C2	0.0364 (10)	0.0412 (9)	0.0369 (9)	0.0050 (7)	0.0088 (7)	0.0147 (7)
C8	0.0393 (10)	0.0392 (9)	0.0429 (9)	0.0043 (8)	0.0046 (8)	0.0162 (8)
C7	0.0427 (11)	0.0492 (10)	0.0432 (10)	0.0095 (8)	0.0026 (8)	0.0237 (8)
C6	0.0646 (13)	0.0448 (10)	0.0387 (10)	0.0092 (9)	0.0153 (9)	0.0171 (8)
C5	0.0464 (11)	0.0484 (10)	0.0510 (11)	0.0180 (9)	0.0251 (9)	0.0202 (9)
C10	0.0498 (11)	0.0471 (10)	0.0519 (11)	0.0210 (9)	0.0181 (9)	0.0218 (9)
C1	0.0360 (9)	0.0351 (9)	0.0392 (9)	0.0098 (7)	0.0110 (7)	0.0179 (7)
C11	0.0564 (12)	0.0384 (10)	0.0507 (10)	0.0156 (9)	0.0175 (9)	0.0228 (8)
C12	0.0575 (13)	0.0317 (9)	0.0449 (10)	0.0066 (9)	0.0153 (9)	0.0208 (8)

Geometric parameters (Å, º) top

O1—C3	1.447 (2)	C8—C7	1.532 (2)
O1—H1	0.815 (15)	C8—H8B	0.9700
O2—C12	1.311 (2)	C8—H8A	0.9700
O2—H2	0.850 (16)	C7—C6	1.527 (3)
O3—C12	1.210 (2)	C7—H7A	0.9800
C4—C3	1.519 (2)	C6—C5	1.520 (3)
C4—C5	1.530 (2)	C6—H6B	0.9700
C4—H4B	0.9700	C6—H6A	0.9700
C4—H4A	0.9700	C5—C10	1.529 (2)
C9—C3	1.519 (2)	C5—H5A	0.9800
C9—C7	1.528 (2)	C10—C1	1.536 (2)
C9—H9B	0.9700	C10—H10B	0.9700
C9—H9A	0.9700	C10—H10A	0.9700
C3—C2	1.525 (2)	C1—C11	1.546 (2)
C2—C1	1.532 (2)	C11—C12	1.493 (2)
C2—H2B	0.9700	C11—H11A	0.9700
C2—H2A	0.9700	C11—H11B	0.9700
C8—C1	1.528 (2)

C3—O1—H1	107.3 (15)	C9—C7—H7A	109.5
C12—O2—H2	110.6 (16)	C8—C7—H7A	109.5
C3—C4—C5	109.05 (14)	C5—C6—C7	109.37 (13)
C3—C4—H4B	109.9	C5—C6—H6B	109.8
C5—C4—H4B	109.9	C7—C6—H6B	109.8
C3—C4—H4A	109.9	C5—C6—H6A	109.8
C5—C4—H4A	109.9	C7—C6—H6A	109.8
H4B—C4—H4A	108.3	H6B—C6—H6A	108.2
C3—C9—C7	109.47 (13)	C6—C5—C10	109.57 (15)
C3—C9—H9B	109.8	C6—C5—C4	109.75 (14)
C7—C9—H9B	109.8	C10—C5—C4	109.33 (14)
C3—C9—H9A	109.8	C6—C5—H5A	109.4
C7—C9—H9A	109.8	C10—C5—H5A	109.4
H9B—C9—H9A	108.2	C4—C5—H5A	109.4
O1—C3—C9	110.50 (14)	C5—C10—C1	110.38 (13)
O1—C3—C4	110.82 (13)	C5—C10—H10B	109.6
C9—C3—C4	109.93 (14)	C1—C10—H10B	109.6
O1—C3—C2	106.48 (13)	C5—C10—H10A	109.6
C9—C3—C2	109.35 (13)	C1—C10—H10A	109.6
C4—C3—C2	109.69 (14)	H10B—C10—H10A	108.1
C3—C2—C1	110.46 (12)	C8—C1—C2	108.35 (13)
C3—C2—H2B	109.6	C8—C1—C10	108.54 (13)
C1—C2—H2B	109.6	C2—C1—C10	108.65 (14)
C3—C2—H2A	109.6	C8—C1—C11	111.84 (14)
C1—C2—H2A	109.6	C2—C1—C11	111.65 (13)
H2B—C2—H2A	108.1	C10—C1—C11	107.71 (13)
C1—C8—C7	110.32 (13)	C12—C11—C1	115.10 (13)
C1—C8—H8B	109.6	C12—C11—H11A	108.5
C7—C8—H8B	109.6	C1—C11—H11A	108.5
C1—C8—H8A	109.6	C12—C11—H11B	108.5
C7—C8—H8A	109.6	C1—C11—H11B	108.5
H8B—C8—H8A	108.1	H11A—C11—H11B	107.5
C6—C7—C9	108.98 (14)	O3—C12—O2	122.43 (17)
C6—C7—C8	109.93 (14)	O3—C12—C11	123.93 (17)
C9—C7—C8	109.30 (13)	O2—C12—C11	113.63 (17)
C6—C7—H7A	109.5

C7—C9—C3—O1	176.98 (12)	C3—C4—C5—C10	60.50 (18)
C7—C9—C3—C4	−60.38 (17)	C6—C5—C10—C1	60.28 (19)
C7—C9—C3—C2	60.09 (17)	C4—C5—C10—C1	−60.04 (19)
C5—C4—C3—O1	−177.88 (13)	C7—C8—C1—C2	−59.16 (17)
C5—C4—C3—C9	59.68 (17)	C7—C8—C1—C10	58.66 (17)
C5—C4—C3—C2	−60.59 (18)	C7—C8—C1—C11	177.35 (14)
O1—C3—C2—C1	−179.80 (13)	C3—C2—C1—C8	59.39 (17)
C9—C3—C2—C1	−60.39 (17)	C3—C2—C1—C10	−58.36 (17)
C4—C3—C2—C1	60.23 (18)	C3—C2—C1—C11	−177.01 (14)
C3—C9—C7—C6	60.25 (16)	C5—C10—C1—C8	−59.19 (18)
C3—C9—C7—C8	−59.91 (18)	C5—C10—C1—C2	58.44 (18)
C1—C8—C7—C6	−59.55 (18)	C5—C10—C1—C11	179.54 (14)
C1—C8—C7—C9	60.02 (18)	C8—C1—C11—C12	53.8 (2)
C9—C7—C6—C5	−60.32 (17)	C2—C1—C11—C12	−67.8 (2)
C8—C7—C6—C5	59.45 (18)	C10—C1—C11—C12	172.94 (15)
C7—C6—C5—C10	−59.72 (18)	C1—C11—C12—O3	−98.6 (2)
C7—C6—C5—C4	60.34 (18)	C1—C11—C12—O2	80.82 (19)
C3—C4—C5—C6	−59.71 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82 (2)	2.00 (2)	2.7959 (18)	168 (2)
O2—H2···O1ⁱⁱ	0.85 (2)	1.81 (2)	2.649 (2)	168 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₈O₃
M_r	210.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5120 (9), 7.9485 (11), 11.5469 (15)
α, β, γ (°)	106.919 (10), 94.838 (10), 104.443 (7)
V (Å³)	545.73 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.98, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	8786, 2488, 1574
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.03
No. of reflections	2488
No. of parameters	142
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.815 (15)	1.995 (16)	2.7959 (18)	168 (2)
O2—H2···O1ⁱⁱ	0.850 (16)	1.811 (16)	2.649 (2)	168 (2)

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

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, F. X. & Yang, Y. (1996). Handbook of Clinic Practical Drugs. Nanjing: Jiangsu Science and Technology Press. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tukada, H. & Mochizuki, K. (2005). J. Mol. Struct. 655, 473–478. Web of Science CSD CrossRef Google Scholar
Zhao, G. L., Feng, Y. L., Hu, X. C. & Kong, L. C. (2003). Chin. J. Appl. Chem. 20, 802–808. Google Scholar

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ISSN: 2056-9890

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doi:10.1107/S1600536808020515

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