1-Hydroxy­cyclo­pentane-1-carboxylic acid

Betz, R.; Klüfers, P.

doi:10.1107/S1600536807042183

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1-Hydroxycyclopentane-1-carboxylic acid

R. Betz and P. Klüfers

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042183/cv2295sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042183/cv2295Isup2.hkl Contains datablock I

CCDC reference: 663669

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R factor = 0.050
wR factor = 0.144
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.614
            Test value =      0.600

Author Response: nearest atom: C24, splitting not indicated

DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.

Author Response: nearest atom: C24, splitting not indicated

PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.61 e/A   
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C24    -   C25     ..       5.18 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14

Author Response: conformationally flexible atom at the end of cyclopentane-ring

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24

Author Response: conformationally flexible atom at the end of cyclopentane-ring

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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).

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

	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].

1-Hydroxycyclopentane-1-carboxylic acid top

Crystal data top

C₆H₁₀O₃	F(000) = 840
M_r = 130.14	D_x = 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

Data collection top

Stoe IPDS diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	2574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
area detection scans	θ_max = 25.9°, θ_min = 2.3°
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	h = −19→19
T_min = 0.977, T_max = 0.989	k = −7→7
13242 measured reflections	l = −24→24

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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F²) = 0.144	Only H-atom displacement parameters refined
S = 0.95	w = 1/[σ²(F_o²) + (0.0525P)²] where P = (F_o² + 2F_c²)/3
3774 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₆H₁₀O₃	V = 1983.4 (3) Å³
M_r = 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)°

Data collection top

Stoe IPDS diffractometer	3774 independent reflections
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	2574 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.051
13242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.144	Only H-atom displacement parameters refined
S = 0.95	Δρ_max = 0.61 e Å⁻³
3774 reflections	Δρ_min = −0.29 e Å⁻³
245 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O212^iv	0.84	1.82	2.6559 (19)	177
O32—H32···O12^v	0.84	1.89	2.710 (2)	166
O311—H311···O312^vi	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
M_r	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)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	13242, 3774, 2574
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···O212^iv	0.84	1.82	2.6559 (19)	176.8
O32—H32···O12^v	0.84	1.89	2.710 (2)	165.9
O311—H311···O312^vi	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.

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