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Acta Cryst. (2007). E63, o3932    [ doi:10.1107/S1600536807042183 ]

1-Hydroxycyclopentane-1-carboxylic acid

R. Betz and P. Klüfers

Abstract top

The title compound, C6H10O3, crystallizes with three independent molecules in the asymmetric unit. In all three molecules, which have similar envelope conformations, the cyclopentane ring is arranged skew to the carboxyl group. Intermolecular O-H...O hydrogen bonds link the molecules into two-dimensional layers parallel to the ab plane.

Comment top

The title compound, C6H10O3, was prepared as chelating molecule bearing the conformationally flexible cyclopentane group. It was obtained upon acidic hydrolysis of the cyanohydrin of cyclopentanone. The cyclopentane ring adopts a skew orientation to the planar carboxyl group. Hydrophobic and hydrophilic sheets alternate along [001] (Figure 2). Each individual hydrophilic sheet is composed of the typical bidentately linked carboxylic-acid dimers. The dimer packing is supported by three symmetrically independent, laterally running, cooperative, linearly infinite hydrogen-bond systems which are exclusively formed by hydroxyl-OH vectors.

The molecular structure (Fig. 1) shows a carboxy- and a hydroxy-group attached to the cyclopentane ring.

The molecular packing (Fig. 2) shows O—H···O intermolecular hydrogen bonds (Table 2).

Related literature top

The title compound was prepared according to a standard procedure (Becker et al., 2001).

Experimental top

The title compound was prepared according to standard procedures (Becker et al., 2001) upon acidic hydrolysis of the cyanohydrin of cyclopentanone. Crystals suitable for X-ray analysis were directly obtained from the crystallized reaction product.

Refinement top

All H atoms were located in a difference map and refined as riding on their parent atoms, with C—H = 0.99 Å and O—H = 0.84 Å. One common isotropic displacement parameter for all H atoms was refined to Uiso(H) = 0.0748 (17).

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: IPDS Software (Stoe & Cie, 1996); data reduction: IPDS Software (Stoe & Cie, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Three independent molecules in asymmetric unit of (I), with atom labels and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of (I), viewed along [0 1 0].
1-Hydroxycyclopentane-1-carboxylic acid top
Crystal data top
C6H10O3F000 = 840
Mr = 130.14Dx = 1.307 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5000 reflections
a = 16.0000 (16) Åθ = 2.3–25.9º
b = 6.3490 (4) ŵ = 0.11 mm−1
c = 19.664 (2) ÅT = 200 (2) K
β = 96.812 (12)ºRod, colourless
V = 1983.4 (3) Å30.50 × 0.20 × 0.11 mm
Z = 12
Data collection top
Stoe IPDS
diffractometer		3774 independent reflections
Radiation source: fine-focus sealed tube2574 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 200(2) Kθmax = 25.9º
area detection scansθmin = 2.3º
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)		h = −19→19
Tmin = 0.977, Tmax = 0.989k = −7→7
13242 measured reflectionsl = −24→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Only H-atom displacement parameters refined
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0525P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3774 reflectionsΔρmax = 0.61 e Å−3
245 parametersΔρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C6H10O3V = 1983.4 (3) Å3
Mr = 130.14Z = 12
Monoclinic, P21/cMo Kα
a = 16.0000 (16) ŵ = 0.11 mm−1
b = 6.3490 (4) ÅT = 200 (2) K
c = 19.664 (2) Å0.50 × 0.20 × 0.11 mm
β = 96.812 (12)º
Data collection top
Stoe IPDS
diffractometer		3774 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)		2574 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.989Rint = 0.051
13242 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050245 parameters
wR(F2) = 0.144Only H-atom displacement parameters refined
S = 0.95Δρmax = 0.61 e Å−3
3774 reflectionsΔρmin = −0.29 e Å−3
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 > 2sigma(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
xyzUiso*/Ueq
O120.19965 (8)0.6718 (2)0.10560 (7)0.0364 (3)
H120.21960.79430.10640.0748 (17)*
O111−0.01397 (10)0.8320 (4)0.06625 (10)0.0740 (7)
H111−0.03530.91890.03700.0748 (17)*
O1120.10236 (10)0.9290 (3)0.02446 (9)0.0517 (5)
C110.06518 (12)0.8249 (4)0.06479 (10)0.0359 (5)
C120.11415 (11)0.6807 (3)0.11629 (10)0.0332 (4)
C130.08053 (14)0.4546 (4)0.11271 (12)0.0432 (5)
H1310.01850.45330.10230.0748 (17)*
H1320.10520.37310.07710.0748 (17)*
C140.1072 (2)0.3651 (5)0.18264 (16)0.0776 (9)
H1410.15810.27680.18190.0748 (17)*
H1420.06180.27660.19750.0748 (17)*
C150.1257 (2)0.5482 (5)0.23127 (13)0.0666 (8)
H1510.09090.53870.26950.0748 (17)*
H1520.18580.54810.25040.0748 (17)*
C160.10471 (16)0.7461 (4)0.19014 (11)0.0460 (6)
H1610.14420.86130.20550.0748 (17)*
H1620.04650.79300.19430.0748 (17)*
O220.28938 (8)0.0287 (2)0.10435 (7)0.0333 (3)
H220.28010.12390.07480.0748 (17)*
O2110.51060 (9)0.0212 (3)0.09287 (7)0.0465 (4)
H2110.53740.01220.05880.0748 (17)*
O2120.40014 (9)−0.0017 (2)0.01254 (7)0.0375 (4)
C210.42968 (12)0.0148 (3)0.07252 (10)0.0324 (4)
C220.37585 (12)0.0299 (4)0.13065 (10)0.0336 (5)
C230.39049 (14)−0.1550 (5)0.18061 (11)0.0476 (6)
H2310.3581−0.28020.16280.0748 (17)*
H2320.4509−0.19240.18840.0748 (17)*
C240.36000 (19)−0.0771 (6)0.24609 (13)0.0733 (10)
H2410.3964−0.13170.28640.0748 (17)*
H2420.3016−0.12470.24890.0748 (17)*
C250.36404 (18)0.1663 (6)0.24395 (12)0.0648 (8)
H2510.30750.22760.24610.0748 (17)*
H2520.40270.22040.28310.0748 (17)*
C260.39636 (15)0.2230 (4)0.17639 (11)0.0490 (6)
H2610.45780.24960.18320.0748 (17)*
H2620.36750.34990.15600.0748 (17)*
O320.25059 (8)0.1270 (2)0.52112 (6)0.0329 (3)
H320.24060.02090.54440.0748 (17)*
O3110.42291 (9)0.0291 (3)0.42673 (7)0.0458 (4)
H3110.47430.01100.43990.0748 (17)*
O3120.41433 (9)0.0178 (3)0.53879 (7)0.0384 (4)
C310.38133 (12)0.0366 (3)0.47965 (9)0.0308 (4)
C320.28721 (12)0.0615 (3)0.46198 (9)0.0312 (4)
C330.26007 (14)0.2220 (4)0.40524 (11)0.0426 (5)
H3310.24520.35810.42520.0748 (17)*
H3320.30600.24600.37650.0748 (17)*
C340.18311 (15)0.1247 (5)0.36266 (12)0.0547 (7)
H3410.13460.22220.36020.0748 (17)*
H3420.19570.09470.31550.0748 (17)*
C350.16372 (14)−0.0772 (4)0.39858 (12)0.0507 (6)
H3510.1399−0.18460.36530.0748 (17)*
H3520.1235−0.05160.43220.0748 (17)*
C360.24874 (12)−0.1463 (4)0.43407 (11)0.0389 (5)
H3610.2834−0.21180.40130.0748 (17)*
H3620.2423−0.24700.47150.0748 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O120.0293 (7)0.0307 (8)0.0486 (8)−0.0011 (6)0.0031 (6)0.0015 (6)
O1110.0356 (9)0.0997 (17)0.0874 (13)0.0133 (10)0.0095 (8)0.0552 (13)
O1120.0425 (9)0.0562 (12)0.0573 (10)0.0042 (7)0.0098 (7)0.0238 (8)
C110.0309 (10)0.0389 (13)0.0388 (10)0.0004 (8)0.0073 (8)0.0037 (9)
C120.0288 (10)0.0323 (12)0.0385 (10)0.0000 (8)0.0035 (7)0.0016 (8)
C130.0361 (11)0.0382 (14)0.0557 (13)−0.0067 (9)0.0068 (9)0.0002 (10)
C140.117 (3)0.045 (2)0.0694 (18)−0.0041 (17)0.0041 (17)0.0184 (14)
C150.095 (2)0.0574 (19)0.0457 (14)0.0041 (15)0.0031 (14)0.0116 (12)
C160.0596 (14)0.0399 (15)0.0392 (11)0.0095 (10)0.0088 (10)−0.0002 (9)
O220.0282 (7)0.0375 (9)0.0346 (7)−0.0020 (6)0.0051 (5)0.0076 (6)
O2110.0289 (7)0.0804 (13)0.0303 (7)−0.0023 (7)0.0040 (6)−0.0044 (7)
O2120.0334 (7)0.0513 (10)0.0278 (7)−0.0028 (6)0.0036 (5)−0.0039 (6)
C210.0308 (10)0.0356 (13)0.0308 (10)−0.0026 (8)0.0035 (7)−0.0010 (8)
C220.0290 (9)0.0425 (13)0.0296 (10)−0.0044 (8)0.0055 (7)0.0016 (8)
C230.0362 (11)0.0629 (17)0.0433 (12)0.0046 (10)0.0024 (9)0.0192 (11)
C240.0648 (18)0.115 (3)0.0420 (14)0.0050 (17)0.0132 (12)0.0246 (16)
C250.0625 (16)0.100 (3)0.0338 (12)−0.0154 (16)0.0128 (11)−0.0114 (13)
C260.0454 (12)0.0672 (18)0.0369 (11)−0.0174 (11)0.0151 (9)−0.0174 (11)
O320.0333 (7)0.0326 (9)0.0342 (7)0.0020 (6)0.0097 (5)−0.0040 (6)
O3110.0302 (7)0.0780 (13)0.0298 (7)0.0093 (7)0.0059 (6)−0.0010 (7)
O3120.0327 (7)0.0554 (11)0.0269 (7)0.0057 (6)0.0023 (5)0.0020 (6)
C310.0311 (10)0.0333 (12)0.0283 (9)0.0035 (8)0.0045 (7)−0.0013 (8)
C320.0309 (10)0.0351 (12)0.0281 (9)0.0046 (8)0.0056 (7)−0.0024 (8)
C330.0421 (12)0.0496 (15)0.0360 (10)0.0099 (10)0.0048 (8)0.0074 (10)
C340.0391 (12)0.084 (2)0.0391 (12)0.0119 (12)−0.0014 (9)0.0080 (12)
C350.0365 (11)0.0659 (18)0.0474 (13)0.0004 (11)−0.0045 (9)−0.0123 (12)
C360.0355 (11)0.0415 (14)0.0392 (11)0.0023 (9)0.0017 (8)−0.0112 (9)
Geometric parameters (Å, °) top
O12—C121.410 (2)C23—H2320.9900
O12—H120.8400C24—C251.547 (5)
O111—C111.271 (3)C24—H2410.9900
O111—H1110.8400C24—H2420.9900
O112—C111.238 (3)C25—C261.525 (3)
C11—C121.513 (3)C25—H2510.9900
C12—C131.532 (3)C25—H2520.9900
C12—C161.535 (3)C26—H2610.9900
C13—C141.503 (4)C26—H2620.9900
C13—H1310.9900O32—C321.425 (2)
C13—H1320.9900O32—H320.8400
C14—C151.512 (4)O311—C311.301 (2)
C14—H1410.9900O311—H3110.8400
C14—H1420.9900O312—C311.225 (2)
C15—C161.510 (4)C31—C321.513 (3)
C15—H1510.9900C32—C361.530 (3)
C15—H1520.9900C32—C331.535 (3)
C16—H1610.9900C33—C341.534 (3)
C16—H1620.9900C33—H3310.9900
O22—C221.418 (2)C33—H3320.9900
O22—H220.8400C34—C351.513 (4)
O211—C211.310 (2)C34—H3410.9900
O211—H2110.8399C34—H3420.9900
O212—C211.222 (2)C35—C361.518 (3)
C21—C221.514 (3)C35—H3510.9900
C22—C231.531 (3)C35—H3520.9900
C22—C261.533 (3)C36—H3610.9900
C23—C241.513 (4)C36—H3620.9900
C23—H2310.9900
C12—O12—H12109.5C23—C24—H241110.4
C11—O111—H111109.5C25—C24—H241110.4
O112—C11—O111123.5 (2)C23—C24—H242110.4
O112—C11—C12120.12 (18)C25—C24—H242110.4
O111—C11—C12116.39 (18)H241—C24—H242108.6
O12—C12—C11111.05 (16)C26—C25—C24106.2 (2)
O12—C12—C13107.29 (17)C26—C25—H251110.5
C11—C12—C13112.65 (17)C24—C25—H251110.5
O12—C12—C16110.98 (17)C26—C25—H252110.5
C11—C12—C16111.61 (17)C24—C25—H252110.5
C13—C12—C16102.92 (18)H251—C25—H252108.7
C14—C13—C12104.6 (2)C25—C26—C22104.6 (2)
C14—C13—H131110.8C25—C26—H261110.8
C12—C13—H131110.8C22—C26—H261110.8
C14—C13—H132110.8C25—C26—H262110.8
C12—C13—H132110.8C22—C26—H262110.8
H131—C13—H132108.9H261—C26—H262108.9
C13—C14—C15107.5 (2)C32—O32—H32109.5
C13—C14—H141110.2C31—O311—H311109.5
C15—C14—H141110.2O312—C31—O311123.52 (17)
C13—C14—H142110.2O312—C31—C32122.24 (17)
C15—C14—H142110.2O311—C31—C32114.19 (16)
H141—C14—H142108.5O32—C32—C31109.73 (14)
C16—C15—C14106.7 (2)O32—C32—C36110.95 (16)
C16—C15—H151110.4C31—C32—C36109.85 (16)
C14—C15—H151110.4O32—C32—C33106.93 (16)
C16—C15—H152110.4C31—C32—C33115.09 (17)
C14—C15—H152110.4C36—C32—C33104.16 (16)
H151—C15—H152108.6C34—C33—C32105.6 (2)
C15—C16—C12104.0 (2)C34—C33—H331110.6
C15—C16—H161111.0C32—C33—H331110.6
C12—C16—H161111.0C34—C33—H332110.6
C15—C16—H162111.0C32—C33—H332110.6
C12—C16—H162111.0H331—C33—H332108.8
H161—C16—H162109.0C35—C34—C33106.38 (18)
C22—O22—H22109.5C35—C34—H341110.5
C21—O211—H211109.5C33—C34—H341110.5
O212—C21—O211123.56 (18)C35—C34—H342110.5
O212—C21—C22123.01 (17)C33—C34—H342110.5
O211—C21—C22113.43 (16)H341—C34—H342108.6
O22—C22—C21110.00 (15)C34—C35—C36103.73 (19)
O22—C22—C23107.33 (16)C34—C35—H351111.0
C21—C22—C23112.24 (18)C36—C35—H351111.0
O22—C22—C26110.50 (18)C34—C35—H352111.0
C21—C22—C26113.11 (17)C36—C35—H352111.0
C23—C22—C26103.35 (18)H351—C35—H352109.0
C24—C23—C22104.8 (2)C35—C36—C32102.47 (18)
C24—C23—H231110.8C35—C36—H361111.3
C22—C23—H231110.8C32—C36—H361111.3
C24—C23—H232110.8C35—C36—H362111.3
C22—C23—H232110.8C32—C36—H362111.3
H231—C23—H232108.9H361—C36—H362109.2
C23—C24—C25106.5 (2)
O112—C11—C12—O12−5.7 (3)C26—C22—C23—C2437.0 (2)
O111—C11—C12—O12174.7 (2)C22—C23—C24—C25−23.2 (3)
O112—C11—C12—C13−126.1 (2)C23—C24—C25—C260.5 (3)
O111—C11—C12—C1354.3 (3)C24—C25—C26—C2222.4 (3)
O112—C11—C12—C16118.7 (2)O22—C22—C26—C2578.0 (2)
O111—C11—C12—C16−60.9 (3)C21—C22—C26—C25−158.19 (19)
O12—C12—C13—C1482.0 (2)C23—C22—C26—C25−36.6 (2)
C11—C12—C13—C14−155.5 (2)O312—C31—C32—O3218.8 (3)
C16—C12—C13—C14−35.2 (2)O311—C31—C32—O32−163.73 (18)
C12—C13—C14—C1520.0 (3)O312—C31—C32—C36−103.4 (2)
C13—C14—C15—C163.3 (4)O311—C31—C32—C3674.0 (2)
C14—C15—C16—C12−25.2 (3)O312—C31—C32—C33139.4 (2)
O12—C12—C16—C15−77.4 (3)O311—C31—C32—C33−43.1 (3)
C11—C12—C16—C15158.2 (2)O32—C32—C33—C34−96.4 (2)
C13—C12—C16—C1537.1 (2)C31—C32—C33—C34141.41 (18)
O212—C21—C22—O22−1.8 (3)C36—C32—C33—C3421.1 (2)
O211—C21—C22—O22178.15 (17)C32—C33—C34—C354.5 (2)
O212—C21—C22—C23117.6 (2)C33—C34—C35—C36−28.5 (2)
O211—C21—C22—C23−62.4 (2)C34—C35—C36—C3241.5 (2)
O212—C21—C22—C26−125.9 (2)O32—C32—C36—C3576.1 (2)
O211—C21—C22—C2654.0 (3)C31—C32—C36—C35−162.41 (17)
O22—C22—C23—C24−79.8 (2)C33—C32—C36—C35−38.6 (2)
C21—C22—C23—C24159.19 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O22i0.841.862.684 (2)165
O111—H111···O112ii0.841.802.624 (2)167
O22—H22···O32iii0.841.932.757 (2)169
O211—H211···O212iv0.841.822.6559 (19)177
O32—H32···O12v0.841.892.710 (2)166
O311—H311···O312vi0.841.792.629 (2)175
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y, −z; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O22i0.841.862.684 (2)165
O111—H111···O112ii0.841.802.624 (2)167
O22—H22···O32iii0.841.932.757 (2)169
O211—H211···O212iv0.841.822.6559 (19)177
O32—H32···O12v0.841.892.710 (2)166
O311—H311···O312vi0.841.792.629 (2)175
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y, −z; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y, −z+1.
Acknowledgements top

The authors thank Dr Peter Mayer and Sandra Albrecht for professional support.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

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