(±)-2-Oxocyclo-penta-neacetic acid: catemeric hydrogen bonding in a γ-keto acid.

The title racemate, C(7)H(10)O(3), aggregates in the solid as acid-to-ketone hydrogen-bonding catemers [O⋯O = 2.7050 (13) Å and O-H⋯O = 166.1 (17)°] having glide-related components. Four such heterochiral chains, paired centrosymmetrically about (, , ) in the cell, proceed through the cell in the 010 direction, with alignment with respect to the c axis of ++--.

Related literature

For background to catemers and hydrogen bonds, see: Barcon et al. (1998 ▶, 2002 ▶); Coté et al. (1996 ▶); DeVita Dufort et al. (2007 ▶); Efthimiopoulos et al. (2009 ▶); Harata et al. (1977 ▶); Lalancette & Thompson (2003 ▶); Lalancette et al. (2006 ▶); Malak et al. (2006 ▶); n class="Chemical">Newman et al. (2002 ▶); Steiner (1997 ▶); Stork et al. (1963 ▶).

Experimental

Crystal data

C7H10O3

M = 142.15

Orthorhombic,

a = 5.3232 (1) Å

b = 12.2981 (3) Å

c = 20.8148 (5) Å

V = 1362.65 (5) Å3

Z = 8

Cu Kα radiation

μ = 0.91 mm−1

T = 100 K

0.37 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.730, T max = 0.915

9810 measured reflections

1197 independent reflections

1147 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.04

1197 reflections

95 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2006 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010708/fl2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010708/fl2241Isup2.hkl

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

C7H10O3	Dx = 1.386 Mg m−3
Mr = 142.15	Melting point: 327 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7778 reflections
a = 5.3232 (1) Å	θ = 4.3–67.1°
b = 12.2981 (3) Å	µ = 0.91 mm−1
c = 20.8148 (5) Å	T = 100 K
V = 1362.65 (5) Å3	Needle, colourless
Z = 8	0.37 × 0.15 × 0.10 mm
F(000) = 608

Bruker SMART CCD APEXII area-detector diffractometer	1197 independent reflections
Radiation source: fine-focus sealed tube	1147 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 67.0°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −6→6
Tmin = 0.730, Tmax = 0.915	k = −14→14
9810 measured reflections	l = −24→24

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.8053P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1197 reflections	Δρmax = 0.26 e Å−3
95 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (4)

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.

	x	y	z	Uiso*/Ueq
O1	1.12228 (17)	0.12579 (7)	0.31120 (4)	0.0196 (3)
C1	0.7561 (2)	0.03606 (10)	0.35627 (6)	0.0156 (3)
H1	0.6138	0.0786	0.3375	0.019*
C2	0.9814 (2)	0.11135 (10)	0.35642 (6)	0.0156 (3)
O2	1.16880 (17)	−0.11081 (7)	0.37021 (4)	0.0205 (3)
O3	1.00596 (18)	−0.22599 (7)	0.29778 (4)	0.0193 (3)
H3	1.131 (4)	−0.2640 (14)	0.3061 (8)	0.029*
C3	0.9997 (2)	0.16595 (11)	0.42143 (6)	0.0209 (3)
H3A	1.0087	0.2460	0.4167	0.025*
H3B	1.1505	0.1407	0.4449	0.025*
C4	0.7603 (3)	0.13271 (11)	0.45681 (6)	0.0213 (3)
H4A	0.6238	0.1858	0.4492	0.026*
H4B	0.7905	0.1268	0.5036	0.026*
C5	0.6948 (2)	0.02124 (11)	0.42777 (6)	0.0192 (3)
H5A	0.7984	−0.0371	0.4470	0.023*
H5B	0.5150	0.0037	0.4341	0.023*
C6	0.7852 (2)	−0.06445 (10)	0.31485 (6)	0.0154 (3)
H6A	0.6307	−0.1088	0.3186	0.018*
H6B	0.8010	−0.0415	0.2694	0.018*
C7	1.0077 (2)	−0.13453 (10)	0.33180 (6)	0.0142 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0220 (5)	0.0169 (5)	0.0198 (5)	−0.0025 (4)	0.0027 (4)	0.0010 (3)
C1	0.0140 (6)	0.0151 (6)	0.0176 (6)	0.0018 (5)	−0.0010 (5)	0.0005 (5)
C2	0.0164 (6)	0.0123 (6)	0.0180 (6)	0.0026 (5)	−0.0013 (5)	0.0027 (5)
O2	0.0191 (5)	0.0196 (5)	0.0228 (5)	0.0020 (4)	−0.0054 (4)	−0.0024 (4)
O3	0.0194 (5)	0.0143 (5)	0.0241 (5)	0.0027 (4)	−0.0031 (4)	−0.0034 (3)
C3	0.0230 (7)	0.0206 (7)	0.0192 (7)	−0.0038 (5)	−0.0008 (5)	−0.0026 (5)
C4	0.0227 (7)	0.0220 (7)	0.0191 (7)	0.0001 (5)	0.0015 (5)	−0.0034 (5)
C5	0.0182 (6)	0.0200 (6)	0.0192 (6)	−0.0015 (5)	0.0036 (5)	−0.0013 (5)
C6	0.0148 (6)	0.0150 (6)	0.0163 (6)	−0.0014 (5)	−0.0011 (5)	0.0002 (5)
C7	0.0150 (6)	0.0134 (6)	0.0141 (6)	−0.0026 (5)	0.0028 (5)	0.0020 (4)

O1—C2	1.2165 (15)	C3—H3A	0.9900
C1—C2	1.5150 (17)	C3—H3B	0.9900
C1—C6	1.5150 (16)	C4—C5	1.5383 (18)
C1—C5	1.5345 (17)	C4—H4A	0.9900
C1—H1	1.0000	C4—H4B	0.9900
C2—C3	1.5138 (17)	C5—H5A	0.9900
O2—C7	1.2082 (15)	C5—H5B	0.9900
O3—C7	1.3292 (15)	C6—C7	1.5066 (17)
O3—H3	0.832 (19)	C6—H6A	0.9900
C3—C4	1.5276 (18)	C6—H6B	0.9900
C2—C1—C6	114.76 (10)	C3—C4—H4B	111.0
C2—C1—C5	103.82 (10)	C5—C4—H4B	111.0
C6—C1—C5	118.47 (10)	H4A—C4—H4B	109.0
C2—C1—H1	106.3	C1—C5—C4	103.12 (10)
C6—C1—H1	106.3	C1—C5—H5A	111.1
C5—C1—H1	106.3	C4—C5—H5A	111.1
O1—C2—C3	125.94 (11)	C1—C5—H5B	111.1
O1—C2—C1	125.14 (11)	C4—C5—H5B	111.1
C3—C2—C1	108.91 (10)	H5A—C5—H5B	109.1
C7—O3—H3	111.1 (12)	C7—C6—C1	114.45 (10)
C2—C3—C4	104.97 (10)	C7—C6—H6A	108.6
C2—C3—H3A	110.8	C1—C6—H6A	108.6
C4—C3—H3A	110.8	C7—C6—H6B	108.6
C2—C3—H3B	110.8	C1—C6—H6B	108.6
C4—C3—H3B	110.8	H6A—C6—H6B	107.6
H3A—C3—H3B	108.8	O2—C7—O3	124.18 (11)
C3—C4—C5	103.78 (10)	O2—C7—C6	125.09 (11)
C3—C4—H4A	111.0	O3—C7—C6	110.72 (10)
C5—C4—H4A	111.0
C6—C1—C2—O1	32.63 (17)	C2—C1—C5—C4	34.53 (12)
C5—C1—C2—O1	163.49 (12)	C6—C1—C5—C4	163.15 (11)
C6—C1—C2—C3	−147.97 (11)	C3—C4—C5—C1	−39.41 (12)
C5—C1—C2—C3	−17.11 (13)	C2—C1—C6—C7	57.31 (14)
O1—C2—C3—C4	172.13 (12)	C5—C1—C6—C7	−66.02 (14)
C1—C2—C3—C4	−7.26 (13)	C1—C6—C7—O2	−7.31 (18)
C2—C3—C4—C5	28.73 (13)	C1—C6—C7—O3	173.81 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.832 (19)	1.890 (19)	2.7050 (13)	166.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.832 (19)	1.890 (19)	2.7050 (13)	166.1 (17)

Symmetry code: (i) .