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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042183/cv2295sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042183/cv2295Isup2.hkl |
CCDC reference: 663669
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.
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).
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).
The title compound was prepared according to a standard procedure (Becker et al., 2001).
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).
![]() | Fig. 1. Three independent molecules in asymmetric unit of (I), with atom labels and displacement ellipsoids drawn at the 50% probability level. |
![]() | Fig. 2. The packing of (I), viewed along [0 1 0]. |
C6H10O3 | F(000) = 840 |
Mr = 130.14 | Dx = 1.307 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5000 reflections |
a = 16.0000 (16) Å | θ = 2.3–25.9° |
b = 6.3490 (4) Å | µ = 0.11 mm−1 |
c = 19.664 (2) Å | T = 200 K |
β = 96.812 (12)° | Rod, colourless |
V = 1983.4 (3) Å3 | 0.50 × 0.20 × 0.11 mm |
Z = 12 |
Stoe IPDS diffractometer | 3774 independent reflections |
Radiation source: fine-focus sealed tube | 2574 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
area detection scans | θmax = 25.9°, θmin = 2.3° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | h = −19→19 |
Tmin = 0.977, Tmax = 0.989 | k = −7→7 |
13242 measured reflections | l = −24→24 |
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)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.144 | Only H-atom displacement parameters refined |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3 |
3774 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C6H10O3 | V = 1983.4 (3) Å3 |
Mr = 130.14 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.0000 (16) Å | µ = 0.11 mm−1 |
b = 6.3490 (4) Å | T = 200 K |
c = 19.664 (2) Å | 0.50 × 0.20 × 0.11 mm |
β = 96.812 (12)° |
Stoe IPDS diffractometer | 3774 independent reflections |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | 2574 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.989 | Rint = 0.051 |
13242 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.144 | Only H-atom displacement parameters refined |
S = 0.95 | Δρmax = 0.61 e Å−3 |
3774 reflections | Δρmin = −0.29 e Å−3 |
245 parameters |
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 | ||
O12 | 0.19965 (8) | 0.6718 (2) | 0.10560 (7) | 0.0364 (3) | |
H12 | 0.2196 | 0.7943 | 0.1064 | 0.0748 (17)* | |
O111 | −0.01397 (10) | 0.8320 (4) | 0.06625 (10) | 0.0740 (7) | |
H111 | −0.0353 | 0.9189 | 0.0370 | 0.0748 (17)* | |
O112 | 0.10236 (10) | 0.9290 (3) | 0.02446 (9) | 0.0517 (5) | |
C11 | 0.06518 (12) | 0.8249 (4) | 0.06479 (10) | 0.0359 (5) | |
C12 | 0.11415 (11) | 0.6807 (3) | 0.11629 (10) | 0.0332 (4) | |
C13 | 0.08053 (14) | 0.4546 (4) | 0.11271 (12) | 0.0432 (5) | |
H131 | 0.0185 | 0.4533 | 0.1023 | 0.0748 (17)* | |
H132 | 0.1052 | 0.3731 | 0.0771 | 0.0748 (17)* | |
C14 | 0.1072 (2) | 0.3651 (5) | 0.18264 (16) | 0.0776 (9) | |
H141 | 0.1581 | 0.2768 | 0.1819 | 0.0748 (17)* | |
H142 | 0.0618 | 0.2766 | 0.1975 | 0.0748 (17)* | |
C15 | 0.1257 (2) | 0.5482 (5) | 0.23127 (13) | 0.0666 (8) | |
H151 | 0.0909 | 0.5387 | 0.2695 | 0.0748 (17)* | |
H152 | 0.1858 | 0.5481 | 0.2504 | 0.0748 (17)* | |
C16 | 0.10471 (16) | 0.7461 (4) | 0.19014 (11) | 0.0460 (6) | |
H161 | 0.1442 | 0.8613 | 0.2055 | 0.0748 (17)* | |
H162 | 0.0465 | 0.7930 | 0.1943 | 0.0748 (17)* | |
O22 | 0.28938 (8) | 0.0287 (2) | 0.10435 (7) | 0.0333 (3) | |
H22 | 0.2801 | 0.1239 | 0.0748 | 0.0748 (17)* | |
O211 | 0.51060 (9) | 0.0212 (3) | 0.09287 (7) | 0.0465 (4) | |
H211 | 0.5374 | 0.0122 | 0.0588 | 0.0748 (17)* | |
O212 | 0.40014 (9) | −0.0017 (2) | 0.01254 (7) | 0.0375 (4) | |
C21 | 0.42968 (12) | 0.0148 (3) | 0.07252 (10) | 0.0324 (4) | |
C22 | 0.37585 (12) | 0.0299 (4) | 0.13065 (10) | 0.0336 (5) | |
C23 | 0.39049 (14) | −0.1550 (5) | 0.18061 (11) | 0.0476 (6) | |
H231 | 0.3581 | −0.2802 | 0.1628 | 0.0748 (17)* | |
H232 | 0.4509 | −0.1924 | 0.1884 | 0.0748 (17)* | |
C24 | 0.36000 (19) | −0.0771 (6) | 0.24609 (13) | 0.0733 (10) | |
H241 | 0.3964 | −0.1317 | 0.2864 | 0.0748 (17)* | |
H242 | 0.3016 | −0.1247 | 0.2489 | 0.0748 (17)* | |
C25 | 0.36404 (18) | 0.1663 (6) | 0.24395 (12) | 0.0648 (8) | |
H251 | 0.3075 | 0.2276 | 0.2461 | 0.0748 (17)* | |
H252 | 0.4027 | 0.2204 | 0.2831 | 0.0748 (17)* | |
C26 | 0.39636 (15) | 0.2230 (4) | 0.17639 (11) | 0.0490 (6) | |
H261 | 0.4578 | 0.2496 | 0.1832 | 0.0748 (17)* | |
H262 | 0.3675 | 0.3499 | 0.1560 | 0.0748 (17)* | |
O32 | 0.25059 (8) | 0.1270 (2) | 0.52112 (6) | 0.0329 (3) | |
H32 | 0.2406 | 0.0209 | 0.5444 | 0.0748 (17)* | |
O311 | 0.42291 (9) | 0.0291 (3) | 0.42673 (7) | 0.0458 (4) | |
H311 | 0.4743 | 0.0110 | 0.4399 | 0.0748 (17)* | |
O312 | 0.41433 (9) | 0.0178 (3) | 0.53879 (7) | 0.0384 (4) | |
C31 | 0.38133 (12) | 0.0366 (3) | 0.47965 (9) | 0.0308 (4) | |
C32 | 0.28721 (12) | 0.0615 (3) | 0.46198 (9) | 0.0312 (4) | |
C33 | 0.26007 (14) | 0.2220 (4) | 0.40524 (11) | 0.0426 (5) | |
H331 | 0.2452 | 0.3581 | 0.4252 | 0.0748 (17)* | |
H332 | 0.3060 | 0.2460 | 0.3765 | 0.0748 (17)* | |
C34 | 0.18311 (15) | 0.1247 (5) | 0.36266 (12) | 0.0547 (7) | |
H341 | 0.1346 | 0.2222 | 0.3602 | 0.0748 (17)* | |
H342 | 0.1957 | 0.0947 | 0.3155 | 0.0748 (17)* | |
C35 | 0.16372 (14) | −0.0772 (4) | 0.39858 (12) | 0.0507 (6) | |
H351 | 0.1399 | −0.1846 | 0.3653 | 0.0748 (17)* | |
H352 | 0.1235 | −0.0516 | 0.4322 | 0.0748 (17)* | |
C36 | 0.24874 (12) | −0.1463 (4) | 0.43407 (11) | 0.0389 (5) | |
H361 | 0.2834 | −0.2118 | 0.4013 | 0.0748 (17)* | |
H362 | 0.2423 | −0.2470 | 0.4715 | 0.0748 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O12 | 0.0293 (7) | 0.0307 (8) | 0.0486 (8) | −0.0011 (6) | 0.0031 (6) | 0.0015 (6) |
O111 | 0.0356 (9) | 0.0997 (17) | 0.0874 (13) | 0.0133 (10) | 0.0095 (8) | 0.0552 (13) |
O112 | 0.0425 (9) | 0.0562 (12) | 0.0573 (10) | 0.0042 (7) | 0.0098 (7) | 0.0238 (8) |
C11 | 0.0309 (10) | 0.0389 (13) | 0.0388 (10) | 0.0004 (8) | 0.0073 (8) | 0.0037 (9) |
C12 | 0.0288 (10) | 0.0323 (12) | 0.0385 (10) | 0.0000 (8) | 0.0035 (7) | 0.0016 (8) |
C13 | 0.0361 (11) | 0.0382 (14) | 0.0557 (13) | −0.0067 (9) | 0.0068 (9) | 0.0002 (10) |
C14 | 0.117 (3) | 0.045 (2) | 0.0694 (18) | −0.0041 (17) | 0.0041 (17) | 0.0184 (14) |
C15 | 0.095 (2) | 0.0574 (19) | 0.0457 (14) | 0.0041 (15) | 0.0031 (14) | 0.0116 (12) |
C16 | 0.0596 (14) | 0.0399 (15) | 0.0392 (11) | 0.0095 (10) | 0.0088 (10) | −0.0002 (9) |
O22 | 0.0282 (7) | 0.0375 (9) | 0.0346 (7) | −0.0020 (6) | 0.0051 (5) | 0.0076 (6) |
O211 | 0.0289 (7) | 0.0804 (13) | 0.0303 (7) | −0.0023 (7) | 0.0040 (6) | −0.0044 (7) |
O212 | 0.0334 (7) | 0.0513 (10) | 0.0278 (7) | −0.0028 (6) | 0.0036 (5) | −0.0039 (6) |
C21 | 0.0308 (10) | 0.0356 (13) | 0.0308 (10) | −0.0026 (8) | 0.0035 (7) | −0.0010 (8) |
C22 | 0.0290 (9) | 0.0425 (13) | 0.0296 (10) | −0.0044 (8) | 0.0055 (7) | 0.0016 (8) |
C23 | 0.0362 (11) | 0.0629 (17) | 0.0433 (12) | 0.0046 (10) | 0.0024 (9) | 0.0192 (11) |
C24 | 0.0648 (18) | 0.115 (3) | 0.0420 (14) | 0.0050 (17) | 0.0132 (12) | 0.0246 (16) |
C25 | 0.0625 (16) | 0.100 (3) | 0.0338 (12) | −0.0154 (16) | 0.0128 (11) | −0.0114 (13) |
C26 | 0.0454 (12) | 0.0672 (18) | 0.0369 (11) | −0.0174 (11) | 0.0151 (9) | −0.0174 (11) |
O32 | 0.0333 (7) | 0.0326 (9) | 0.0342 (7) | 0.0020 (6) | 0.0097 (5) | −0.0040 (6) |
O311 | 0.0302 (7) | 0.0780 (13) | 0.0298 (7) | 0.0093 (7) | 0.0059 (6) | −0.0010 (7) |
O312 | 0.0327 (7) | 0.0554 (11) | 0.0269 (7) | 0.0057 (6) | 0.0023 (5) | 0.0020 (6) |
C31 | 0.0311 (10) | 0.0333 (12) | 0.0283 (9) | 0.0035 (8) | 0.0045 (7) | −0.0013 (8) |
C32 | 0.0309 (10) | 0.0351 (12) | 0.0281 (9) | 0.0046 (8) | 0.0056 (7) | −0.0024 (8) |
C33 | 0.0421 (12) | 0.0496 (15) | 0.0360 (10) | 0.0099 (10) | 0.0048 (8) | 0.0074 (10) |
C34 | 0.0391 (12) | 0.084 (2) | 0.0391 (12) | 0.0119 (12) | −0.0014 (9) | 0.0080 (12) |
C35 | 0.0365 (11) | 0.0659 (18) | 0.0474 (13) | 0.0004 (11) | −0.0045 (9) | −0.0123 (12) |
C36 | 0.0355 (11) | 0.0415 (14) | 0.0392 (11) | 0.0023 (9) | 0.0017 (8) | −0.0112 (9) |
O12—C12 | 1.410 (2) | C23—H232 | 0.9900 |
O12—H12 | 0.8400 | C24—C25 | 1.547 (5) |
O111—C11 | 1.271 (3) | C24—H241 | 0.9900 |
O111—H111 | 0.8400 | C24—H242 | 0.9900 |
O112—C11 | 1.238 (3) | C25—C26 | 1.525 (3) |
C11—C12 | 1.513 (3) | C25—H251 | 0.9900 |
C12—C13 | 1.532 (3) | C25—H252 | 0.9900 |
C12—C16 | 1.535 (3) | C26—H261 | 0.9900 |
C13—C14 | 1.503 (4) | C26—H262 | 0.9900 |
C13—H131 | 0.9900 | O32—C32 | 1.425 (2) |
C13—H132 | 0.9900 | O32—H32 | 0.8400 |
C14—C15 | 1.512 (4) | O311—C31 | 1.301 (2) |
C14—H141 | 0.9900 | O311—H311 | 0.8400 |
C14—H142 | 0.9900 | O312—C31 | 1.225 (2) |
C15—C16 | 1.510 (4) | C31—C32 | 1.513 (3) |
C15—H151 | 0.9900 | C32—C36 | 1.530 (3) |
C15—H152 | 0.9900 | C32—C33 | 1.535 (3) |
C16—H161 | 0.9900 | C33—C34 | 1.534 (3) |
C16—H162 | 0.9900 | C33—H331 | 0.9900 |
O22—C22 | 1.418 (2) | C33—H332 | 0.9900 |
O22—H22 | 0.8400 | C34—C35 | 1.513 (4) |
O211—C21 | 1.310 (2) | C34—H341 | 0.9900 |
O211—H211 | 0.8399 | C34—H342 | 0.9900 |
O212—C21 | 1.222 (2) | C35—C36 | 1.518 (3) |
C21—C22 | 1.514 (3) | C35—H351 | 0.9900 |
C22—C23 | 1.531 (3) | C35—H352 | 0.9900 |
C22—C26 | 1.533 (3) | C36—H361 | 0.9900 |
C23—C24 | 1.513 (4) | C36—H362 | 0.9900 |
C23—H231 | 0.9900 | ||
C12—O12—H12 | 109.5 | C23—C24—H241 | 110.4 |
C11—O111—H111 | 109.5 | C25—C24—H241 | 110.4 |
O112—C11—O111 | 123.5 (2) | C23—C24—H242 | 110.4 |
O112—C11—C12 | 120.12 (18) | C25—C24—H242 | 110.4 |
O111—C11—C12 | 116.39 (18) | H241—C24—H242 | 108.6 |
O12—C12—C11 | 111.05 (16) | C26—C25—C24 | 106.2 (2) |
O12—C12—C13 | 107.29 (17) | C26—C25—H251 | 110.5 |
C11—C12—C13 | 112.65 (17) | C24—C25—H251 | 110.5 |
O12—C12—C16 | 110.98 (17) | C26—C25—H252 | 110.5 |
C11—C12—C16 | 111.61 (17) | C24—C25—H252 | 110.5 |
C13—C12—C16 | 102.92 (18) | H251—C25—H252 | 108.7 |
C14—C13—C12 | 104.6 (2) | C25—C26—C22 | 104.6 (2) |
C14—C13—H131 | 110.8 | C25—C26—H261 | 110.8 |
C12—C13—H131 | 110.8 | C22—C26—H261 | 110.8 |
C14—C13—H132 | 110.8 | C25—C26—H262 | 110.8 |
C12—C13—H132 | 110.8 | C22—C26—H262 | 110.8 |
H131—C13—H132 | 108.9 | H261—C26—H262 | 108.9 |
C13—C14—C15 | 107.5 (2) | C32—O32—H32 | 109.5 |
C13—C14—H141 | 110.2 | C31—O311—H311 | 109.5 |
C15—C14—H141 | 110.2 | O312—C31—O311 | 123.52 (17) |
C13—C14—H142 | 110.2 | O312—C31—C32 | 122.24 (17) |
C15—C14—H142 | 110.2 | O311—C31—C32 | 114.19 (16) |
H141—C14—H142 | 108.5 | O32—C32—C31 | 109.73 (14) |
C16—C15—C14 | 106.7 (2) | O32—C32—C36 | 110.95 (16) |
C16—C15—H151 | 110.4 | C31—C32—C36 | 109.85 (16) |
C14—C15—H151 | 110.4 | O32—C32—C33 | 106.93 (16) |
C16—C15—H152 | 110.4 | C31—C32—C33 | 115.09 (17) |
C14—C15—H152 | 110.4 | C36—C32—C33 | 104.16 (16) |
H151—C15—H152 | 108.6 | C34—C33—C32 | 105.6 (2) |
C15—C16—C12 | 104.0 (2) | C34—C33—H331 | 110.6 |
C15—C16—H161 | 111.0 | C32—C33—H331 | 110.6 |
C12—C16—H161 | 111.0 | C34—C33—H332 | 110.6 |
C15—C16—H162 | 111.0 | C32—C33—H332 | 110.6 |
C12—C16—H162 | 111.0 | H331—C33—H332 | 108.8 |
H161—C16—H162 | 109.0 | C35—C34—C33 | 106.38 (18) |
C22—O22—H22 | 109.5 | C35—C34—H341 | 110.5 |
C21—O211—H211 | 109.5 | C33—C34—H341 | 110.5 |
O212—C21—O211 | 123.56 (18) | C35—C34—H342 | 110.5 |
O212—C21—C22 | 123.01 (17) | C33—C34—H342 | 110.5 |
O211—C21—C22 | 113.43 (16) | H341—C34—H342 | 108.6 |
O22—C22—C21 | 110.00 (15) | C34—C35—C36 | 103.73 (19) |
O22—C22—C23 | 107.33 (16) | C34—C35—H351 | 111.0 |
C21—C22—C23 | 112.24 (18) | C36—C35—H351 | 111.0 |
O22—C22—C26 | 110.50 (18) | C34—C35—H352 | 111.0 |
C21—C22—C26 | 113.11 (17) | C36—C35—H352 | 111.0 |
C23—C22—C26 | 103.35 (18) | H351—C35—H352 | 109.0 |
C24—C23—C22 | 104.8 (2) | C35—C36—C32 | 102.47 (18) |
C24—C23—H231 | 110.8 | C35—C36—H361 | 111.3 |
C22—C23—H231 | 110.8 | C32—C36—H361 | 111.3 |
C24—C23—H232 | 110.8 | C35—C36—H362 | 111.3 |
C22—C23—H232 | 110.8 | C32—C36—H362 | 111.3 |
H231—C23—H232 | 108.9 | H361—C36—H362 | 109.2 |
C23—C24—C25 | 106.5 (2) | ||
O112—C11—C12—O12 | −5.7 (3) | C26—C22—C23—C24 | 37.0 (2) |
O111—C11—C12—O12 | 174.7 (2) | C22—C23—C24—C25 | −23.2 (3) |
O112—C11—C12—C13 | −126.1 (2) | C23—C24—C25—C26 | 0.5 (3) |
O111—C11—C12—C13 | 54.3 (3) | C24—C25—C26—C22 | 22.4 (3) |
O112—C11—C12—C16 | 118.7 (2) | O22—C22—C26—C25 | 78.0 (2) |
O111—C11—C12—C16 | −60.9 (3) | C21—C22—C26—C25 | −158.19 (19) |
O12—C12—C13—C14 | 82.0 (2) | C23—C22—C26—C25 | −36.6 (2) |
C11—C12—C13—C14 | −155.5 (2) | O312—C31—C32—O32 | 18.8 (3) |
C16—C12—C13—C14 | −35.2 (2) | O311—C31—C32—O32 | −163.73 (18) |
C12—C13—C14—C15 | 20.0 (3) | O312—C31—C32—C36 | −103.4 (2) |
C13—C14—C15—C16 | 3.3 (4) | O311—C31—C32—C36 | 74.0 (2) |
C14—C15—C16—C12 | −25.2 (3) | O312—C31—C32—C33 | 139.4 (2) |
O12—C12—C16—C15 | −77.4 (3) | O311—C31—C32—C33 | −43.1 (3) |
C11—C12—C16—C15 | 158.2 (2) | O32—C32—C33—C34 | −96.4 (2) |
C13—C12—C16—C15 | 37.1 (2) | C31—C32—C33—C34 | 141.41 (18) |
O212—C21—C22—O22 | −1.8 (3) | C36—C32—C33—C34 | 21.1 (2) |
O211—C21—C22—O22 | 178.15 (17) | C32—C33—C34—C35 | 4.5 (2) |
O212—C21—C22—C23 | 117.6 (2) | C33—C34—C35—C36 | −28.5 (2) |
O211—C21—C22—C23 | −62.4 (2) | C34—C35—C36—C32 | 41.5 (2) |
O212—C21—C22—C26 | −125.9 (2) | O32—C32—C36—C35 | 76.1 (2) |
O211—C21—C22—C26 | 54.0 (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—C24 | 159.19 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O22i | 0.84 | 1.86 | 2.684 (2) | 165 |
O111—H111···O112ii | 0.84 | 1.80 | 2.624 (2) | 167 |
O22—H22···O32iii | 0.84 | 1.93 | 2.757 (2) | 169 |
O211—H211···O212iv | 0.84 | 1.82 | 2.6559 (19) | 177 |
O32—H32···O12v | 0.84 | 1.89 | 2.710 (2) | 166 |
O311—H311···O312vi | 0.84 | 1.79 | 2.629 (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. |
Experimental details
Crystal data | |
Chemical formula | C6H10O3 |
Mr | 130.14 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 16.0000 (16), 6.3490 (4), 19.664 (2) |
β (°) | 96.812 (12) |
V (Å3) | 1983.4 (3) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.20 × 0.11 |
Data collection | |
Diffractometer | Stoe IPDS |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1997) |
Tmin, Tmax | 0.977, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13242, 3774, 2574 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.613 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.144, 0.95 |
No. of reflections | 3774 |
No. of parameters | 245 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.61, −0.29 |
Computer programs: IPDS Software (Stoe & Cie, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O22i | 0.84 | 1.86 | 2.684 (2) | 165.0 |
O111—H111···O112ii | 0.84 | 1.80 | 2.624 (2) | 167.0 |
O22—H22···O32iii | 0.84 | 1.93 | 2.757 (2) | 168.8 |
O211—H211···O212iv | 0.84 | 1.82 | 2.6559 (19) | 176.8 |
O32—H32···O12v | 0.84 | 1.89 | 2.710 (2) | 165.9 |
O311—H311···O312vi | 0.84 | 1.79 | 2.629 (2) | 175.1 |
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. |
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).