4-Oxocyclo­hexa­neacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enanti­omer in an achiral ∊-keto acid

Barcon, A.; Brunskill, A.P.J.; Lalancette, R.A.; Thompson, H.W.

doi:10.1107/S1600536810036652

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2576-o2577

doi:10.1107/S1600536810036652

Open

access

4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enantiomer in an achiral ∊-keto acid

Alan Barcon,^a Andrew P. J. Brunskill,^a Roger A. Lalancette ^a ^* and Hugh W. Thompson ^a

^aCarl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102, USA
^*Correspondence e-mail: rogerlal@andromeda.rutgers.edu

(Received 8 September 2010; accepted 13 September 2010; online 18 September 2010)

The asymmetric unit of the title compound, C₈H₁₂O₃, consists of a single conformational enantiomer, which aggregates in the catemeric acid-to-ketone hydrogen-bonding mode [O⋯O = 2.682 (4) Å and O—H⋯O = 172 (6)°]. Four hydrogen-bonding chains of translationally related molecules pass through the cell orthogonal to the 4₃ screw axis along c, alternating in the 110 and the $[\overline{1}]$ 10 direction, with alignment with respect to this axis of + + − −. Successive chains are rotated by 90° around the c axis. One C—H⋯O=C close contact, involving the carboxyl group, exists.

Related literature

For a discussion of highly ordered carboxyl bond distances and angles, see: Borthwick (1980 ). For close contact information, see: Steiner (1997 ). For related structures, see: Abell et al. (1991 ); Chen et al. (2000 ); Desiraju (1989 ); Halfpenny (1990 ); Jacques et al. (1981 ); Kawai et al. (1985 ); McGuire et al. (1995 ). For background information regarding the crystallization of a single chiral conformer from a racemic solution, see: Kondepudi et al. (1990 ). For anti-isoketopinic acid, see: Lalancette et al. (1997 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₈H₁₂O₃
M_r = 156.18
Tetragonal, P 4₃
a = 6.8531 (12) Å
c = 17.372 (3) Å
V = 815.9 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 100 K
0.28 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.806, T_max = 0.882
6963 measured reflections
1310 independent reflections
1274 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.18
1310 reflections
105 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 559 Friedel pairs
Flack parameter: 0.0 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.75 (6)	1.94 (6)	2.682 (4)	172 (6)
C7—H7A⋯O2ⁱⁱ	0.99	2.51	3.439 (5)	156
Symmetry codes: (i) x-1, y-1, z; (ii) $[y, -x+1, z+{\script{1\over 4}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2005 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036652/sj5037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036652/sj5037Isup2.hkl

checkCIF report

Comment top

The similar carbonyl basicities of carboxylic acids and ketones allow the two to compete as hydrogen-bond acceptors. Hence, simple keto acids display three known solid-state H-bonding modes beyond those seen in functionally unelaborated acids. The commonest, acid-to-ketone catemerization, constitutes a sizable minority of cases. The title compound aggregates as a catemer and crystallizes with only a single chiral conformer present.

Fig. 1 offers a view of the asymmetric unit. The expected staggering of substituents at C1 and C7 minimizes interactions with the axial H atoms at C2 and C6 by rotating the carboxyl away from the central O1—C4—C1—C7 plane, thus producing a chiral conformation. The C2—C1—C7—C8 torsion angle is -66.9 (4)° and the C1—C7—C8—O2 torsion angle is -9.9 (6)°.

The averaging of C—O bond lengths and C—C—O angles by disorder, common in carboxyl dimers, is not observed in catemers whose geometry cannot support the underlying averaging mechanisms involved. Here, these lengths and angles are typical of those for highly ordered dimeric carboxyls and catemers (Borthwick, 1980).

Fig. 2 shows the packing of the cell, with extracellular molecules to illustrate the H-bonding aggregation as translational carboxyl-to-ketone catemers around the 4₃ screw axis coinciding with the c cell edge [O···O = 2.682 (4) Å, O—H···O = 172 (6)°]. Successive molecules in a given H-bonding chain advance alternately along the 110 and the -110 directions, with alignment with respect to the c axis of + + - -. Successive chains around the c axis are rotated by 90°. The structure therefore is comprised of stacked sheets in four orientations, each layer consisting of parallel H-bonding chains laid side-by-side. The arrangement is nearly identical with that we have previously reported for anti-isoketopinic acid (Lalancette et al., 1997).

We characterize the geometry of H bonding to carbonyls using a combination of H···O=C angle and H···O=C—C torsion angle. These describe the approach of the acid H atom to the receptor O in terms of its deviation from, respectively, C=O axiality (ideal = 120°) and coplanarity with the carbonyl (ideal = 0°). Here, these two angles are 128.6 (16) and -1.2 (19)°.

Within the 2.6 Å range we survey for non-bonded C—H···O packing interactions (Steiner, 1997), only one close contact was found (see Table 2).

Although crystallization in space group P4₃ is itself quite unusual (ca 0.12% of compounds in the Cambridge database), an equally unusual aspect of the packing is the presence of only a single chiral conformer. Preferential crystallization of one chiral conformer from solutions of an inherently achiral molecule is very rare but far from unknown (Jacques et al., 1981; Desiraju, 1989). Among keto acids, five cases are known of this phenomenon: [Cambridge Structural Database (CSD, Version 5.28, update of Nov., 2006; Allen, 2002) refcodes CUHCUD (Kawai et al., 1985), JISVAI (Abell et al., 1991), KICRIX (Halfpenny, 1990) & ZEMJIK (McGuire et al., 1995)], plus the case of mesitylglyoxylic acid (Chen et al., 2000). The particular antipode crystallizing from such a solution may depend merely on which one chances to crystallize first, and it has been shown in a similar case that stirring seeds the solution and may largely or entirely prevent the enantiomeric species from crystallizing (Kondepudi et al., 1990). In the present instance, the Flack parameter allows us to assign a specific hand to (I), so the antipode actually illustrated is the correct one. Also, the octant rule predicts that the conformer should have (-) rotation.

Related literature top

For a discussion of highly ordered carboxyl bond distances and angles, see: Borthwick (1980). For close contact information, see: Steiner (1997). For related structures, see: Abell et al. (1991); Chen et al. (2000); Desiraju (1989); Halfpenny (1990); Jacques et al. (1981); Kawai et al. (1985); McGuire et al. (1995). For background information regarding the crystallization of a single chiral conformer from a racemic solution, see: Kondepudi et al. (1990). For anti-isoketopinic acid, see: Lalancette et al. (1997). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The solid-state (KBr) infrared spectrum of (I) has C=O stretching absorptions at 1726 and 1685 cm^-1, consistent with known shifts produced when H-bonding is removed from carboxyl C=O and added to a ketone, respectively. In CHCl₃ solution, these bands coalesce to a single absorption at 1707 cm^-1, with a typical carboxyl-dilution shoulder around 1755 cm^-1.

The title compound was prepared by Jones oxidation of the product obtained by catalytic hydrogenation of p-hydroxyphenylacetic acid over a Rh/C catalyst. The crystal used was obtained from Et₂O/cyclohexane (60:40 v/v) by evaporation, mp 345 K.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. A view of the asymmetric unit with its numbering. Displacement ellipsoids are set at the 40% probability level.

Fig. 2. A packing diagram, with extracellular molecules, showing the four catemers created by acid-to-ketone H bonds proceeding along chains of translationally related molecules, advancing alternately along the 110 and the -110 directions. These chains have alignment with respect to the c axis of + + - -. All non-carboxyl H atoms have been removed for clarity. Displacement ellipsoids are set at the 30% probability level.

4-Oxocyclohexaneacetic acid top

Crystal data top

C₈H₁₂O₃	D_x = 1.271 Mg m⁻³
M_r = 156.18	Melting point: 345 K
Tetragonal, P4₃	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 4cw	Cell parameters from 6759 reflections
a = 6.8531 (12) Å	θ = 5.1–70.5°
c = 17.372 (3) Å	µ = 0.80 mm⁻¹
V = 815.9 (3) Å³	T = 100 K
Z = 4	Block, colourless
F(000) = 336	0.28 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1310 independent reflections
Radiation source: fine-focus sealed tube	1274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 70.8°, θ_min = 6.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −7→7
T_min = 0.806, T_max = 0.882	k = −8→7
6963 measured reflections	l = −20→18

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0369P)² + 0.671P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 1.18	Δρ_max = 0.17 e Å⁻³
1310 reflections	Δρ_min = −0.20 e Å⁻³
105 parameters	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0023 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 559 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (4)

Crystal data top

C₈H₁₂O₃	Z = 4
M_r = 156.18	Cu Kα radiation
Tetragonal, P4₃	µ = 0.80 mm⁻¹
a = 6.8531 (12) Å	T = 100 K
c = 17.372 (3) Å	0.28 × 0.20 × 0.16 mm
V = 815.9 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1310 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	1274 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.882	R_int = 0.029
6963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.113	Δρ_max = 0.17 e Å⁻³
S = 1.18	Δρ_min = −0.20 e Å⁻³
1310 reflections	Absolute structure: Flack (1983), 559 Friedel pairs
105 parameters	Absolute structure parameter: 0.0 (4)
1 restraint

Special details top

Experimental. crystal mounted on a Cryoloop using Paratone-N

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	0.9958 (3)	1.2372 (3)	0.08526 (13)	0.0341 (5)
O2	0.2472 (4)	0.6544 (3)	0.03744 (14)	0.0460 (6)
O3	0.1245 (4)	0.5683 (4)	0.15016 (13)	0.0421 (6)
H3	0.083 (6)	0.482 (6)	0.130 (2)	0.036 (11)*
C1	0.4571 (4)	0.9768 (4)	0.10334 (18)	0.0275 (6)
H1	0.3956	1.0155	0.0534	0.033*
C2	0.6441 (4)	0.8617 (4)	0.08592 (17)	0.0289 (7)
H2A	0.7056	0.8208	0.1349	0.035*
H2B	0.6105	0.7426	0.0565	0.035*
C3	0.7890 (4)	0.9841 (4)	0.03955 (19)	0.0299 (6)
H3A	0.9128	0.9109	0.0342	0.036*
H3B	0.7358	1.0064	−0.0127	0.036*
C4	0.8297 (4)	1.1764 (4)	0.07670 (18)	0.0294 (7)
C5	0.6532 (5)	1.2912 (4)	0.10375 (19)	0.0340 (7)
H5A	0.5867	1.3494	0.0587	0.041*
H5B	0.6967	1.3990	0.1376	0.041*
C6	0.5086 (4)	1.1616 (4)	0.14778 (18)	0.0309 (7)
H6A	0.5662	1.1249	0.1980	0.037*
H6B	0.3879	1.2365	0.1580	0.037*
C7	0.3105 (4)	0.8534 (4)	0.14873 (17)	0.0284 (6)
H7A	0.3757	0.8031	0.1956	0.034*
H7B	0.2019	0.9386	0.1656	0.034*
C8	0.2272 (4)	0.6841 (4)	0.10499 (17)	0.0285 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0344 (12)	0.0356 (12)	0.0322 (12)	−0.0107 (9)	−0.0004 (9)	0.0009 (9)
O2	0.0644 (16)	0.0488 (14)	0.0248 (12)	−0.0289 (12)	0.0023 (12)	−0.0052 (10)
O3	0.0544 (15)	0.0413 (14)	0.0305 (12)	−0.0195 (12)	0.0077 (11)	−0.0039 (11)
C1	0.0327 (15)	0.0281 (15)	0.0217 (14)	−0.0034 (12)	−0.0037 (12)	0.0028 (12)
C2	0.0366 (16)	0.0244 (15)	0.0258 (16)	−0.0003 (12)	−0.0009 (13)	−0.0002 (12)
C3	0.0321 (16)	0.0318 (15)	0.0257 (15)	0.0002 (12)	−0.0033 (13)	0.0002 (13)
C4	0.0353 (16)	0.0308 (15)	0.0222 (14)	−0.0054 (13)	−0.0014 (13)	0.0070 (12)
C5	0.0407 (18)	0.0254 (16)	0.0358 (18)	−0.0041 (13)	−0.0004 (14)	−0.0018 (13)
C6	0.0282 (15)	0.0294 (16)	0.0352 (17)	0.0007 (11)	−0.0004 (13)	−0.0025 (14)
C7	0.0311 (15)	0.0299 (15)	0.0244 (15)	−0.0004 (11)	−0.0004 (12)	0.0015 (12)
C8	0.0270 (15)	0.0351 (16)	0.0234 (16)	0.0001 (12)	−0.0016 (12)	0.0002 (12)

Geometric parameters (Å, º) top

O1—C4	1.222 (4)	C3—H3A	0.9900
O2—C8	1.199 (4)	C3—H3B	0.9900
O3—C8	1.319 (4)	C4—C5	1.518 (4)
O3—H3	0.74 (4)	C5—C6	1.535 (4)
C1—C6	1.524 (4)	C5—H5A	0.9900
C1—C7	1.532 (4)	C5—H5B	0.9900
C1—C2	1.535 (4)	C6—H6A	0.9900
C1—H1	1.0000	C6—H6B	0.9900
C2—C3	1.529 (4)	C7—C8	1.500 (4)
C2—H2A	0.9900	C7—H7A	0.9900
C2—H2B	0.9900	C7—H7B	0.9900
C3—C4	1.494 (4)

C8—O3—H3	114 (3)	C4—C5—C6	111.6 (2)
C6—C1—C7	110.5 (2)	C4—C5—H5A	109.3
C6—C1—C2	109.5 (2)	C6—C5—H5A	109.3
C7—C1—C2	111.4 (2)	C4—C5—H5B	109.3
C6—C1—H1	108.5	C6—C5—H5B	109.3
C7—C1—H1	108.5	H5A—C5—H5B	108.0
C2—C1—H1	108.5	C1—C6—C5	112.2 (2)
C3—C2—C1	111.4 (2)	C1—C6—H6A	109.2
C3—C2—H2A	109.4	C5—C6—H6A	109.2
C1—C2—H2A	109.4	C1—C6—H6B	109.2
C3—C2—H2B	109.4	C5—C6—H6B	109.2
C1—C2—H2B	109.4	H6A—C6—H6B	107.9
H2A—C2—H2B	108.0	C8—C7—C1	114.6 (2)
C4—C3—C2	112.2 (3)	C8—C7—H7A	108.6
C4—C3—H3A	109.2	C1—C7—H7A	108.6
C2—C3—H3A	109.2	C8—C7—H7B	108.6
C4—C3—H3B	109.2	C1—C7—H7B	108.6
C2—C3—H3B	109.2	H7A—C7—H7B	107.6
H3A—C3—H3B	107.9	O2—C8—O3	122.8 (3)
O1—C4—C3	121.8 (3)	O2—C8—C7	125.7 (3)
O1—C4—C5	121.9 (3)	O3—C8—C7	111.5 (3)
C3—C4—C5	116.3 (3)

C6—C1—C2—C3	−58.4 (3)	C7—C1—C6—C5	−179.2 (2)
C7—C1—C2—C3	179.1 (2)	C2—C1—C6—C5	57.8 (3)
C1—C2—C3—C4	52.9 (3)	C4—C5—C6—C1	−51.0 (3)
C2—C3—C4—O1	132.3 (3)	C6—C1—C7—C8	171.1 (2)
C2—C3—C4—C5	−47.3 (4)	C2—C1—C7—C8	−67.0 (3)
O1—C4—C5—C6	−133.5 (3)	C1—C7—C8—O2	−9.6 (4)
C3—C4—C5—C6	46.0 (4)	C1—C7—C8—O3	171.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.75 (6)	1.94 (6)	2.682 (4)	172 (6)
C7—H7A···O2ⁱⁱ	0.99	2.51	3.439 (5)	156

Symmetry codes: (i) x−1, y−1, z; (ii) y, −x+1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₈H₁₂O₃
M_r	156.18
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	100
a, c (Å)	6.8531 (12), 17.372 (3)
V (Å³)	815.9 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.28 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.806, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	6963, 1310, 1274
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.18
No. of reflections	1310
No. of parameters	105
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20
Absolute structure	Flack (1983), 559 Friedel pairs
Absolute structure parameter	0.0 (4)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.75 (6)	1.94 (6)	2.682 (4)	172 (6)
C7—H7A···O2ⁱⁱ	0.99	2.51	3.439 (5)	156

Symmetry codes: (i) x−1, y−1, z; (ii) y, −x+1, z+1/4.

Acknowledgements

The authors acknowledge support by NSF-CRIF grant No. 0443538. This paper is dedicated to the memory of HWT: he was a wonderful mentor, teacher and friend at Rutgers University-Newark for 44 years; he will surely be missed.

References

Abell, A. D., Trent, J. O. & Morris, K. B. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1077–1083. CSD CrossRef Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Borthwick, P. W. (1980). Acta Cryst. B36, 628–632. CrossRef CAS IUCr Journals Web of Science Google Scholar
Bruker (2005). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, C.-D., Brunskill, A. P. J., Hall, S. S., Lalancette, R. A. & Thompson, H. W. (2000). Acta Cryst. C56, 1148–1151. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Desiraju, G. R. (1989). Crystal Engineering: the Design of Organic Solids, pp. 240–244. New York : Elsevier. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Halfpenny, J. (1990). Acta Cryst. C46, 2487–2489. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Jacques, J., Collet, A. & Wilen, S. H. (1981). Enantiomers, Racemates, and Resolution, pp. 14–15. New York: Wiley–Interscience. Google Scholar
Kawai, K.-I., Ito, H., Nagase, H., Yamaguchi, R. & Nakajima, S. (1985). Acta Cryst. C41, 415–417. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kondepudi, D. K., Kaufman, R. J. & Singh, N. (1990). Science, 250, 975–977. CrossRef PubMed CAS Web of Science Google Scholar
Lalancette, R. A., Coté, M. L. & Thompson, H. W. (1997). Acta Cryst. C53, 370–372. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
McGuire, J. N., Wilson, S. R. & Rinehart, K. L. (1995). J. Antibiot. 48, 516–519. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steiner, T. (1997). Chem. Commun. pp. 727–734. CrossRef Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2576-o2577

doi:10.1107/S1600536810036652

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-Oxo­cyclo­hexa­ne­acetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enanti­omer in an achiral ∊-keto acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enantiomer in an achiral ∊-keto acid