Download citation
Download citation
link to html
The orthorhombic form of 2-hydroxy­cyclo­pent-2-enone, C5H6O2, consists of chains of hydrogen-bonded mol­ecules aligned along a twofold screw axis. The monoclinic form contains two independent mol­ecules, which have different orientations of the hydroxyl proton, and which assemble into ribbons along a twofold screw axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009550/de1148sup1.cif
Contains datablocks global, 3sm1, 3sm2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009550/de11483sm1sup2.hkl
Contains datablock 3sm1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009550/de11483sm2sup3.hkl
Contains datablock 3sm2

CCDC references: 152622; 152623

Comment top

As part of a study of the Maillard chemistry of dehydroascorbic acid and its decomposition products (Fayle et al., 2000), we have reported the ability of the food-additive cyclotene (I) to act as a cross-linking reagent for model proteins (Fayle et al., 1999). Recently (Fayle et al., 1998), we reported the X-ray crystal structure of the crystalline hydrate of cyclotene, which exists as the hydroxyenone tautomer, (Ib). In a similar context, we are presently investigating the chemistry of the parent diketone (II), which NMR solution studies clearly show exists as the enol tautomer, (IIb). However, this compound displays chemistry that can be attributed to both the diketo tautomer, (IIa), and the enol tautomer, (IIb). During the course of this work, we managed to isolate two crystalline modifications of (II), which raised the intriguing possibility that these might be different stable tautomers of the same compound [a rare phenomenom sometimes called desmotropy (Guard & Steel, 1994; Desiraju, 1983)]. We now report the structures of these two crystalline forms. \sch

The molecular structure in the orthorhombic form is shown in Fig. 1. The successful location and refinement of the potentially tautomeric hydroxyl H atom, along with the bonding geometry (Table 1), unambiguously establish that, in this form, the title compound exists as the hydroxyenone tautomer, (IIb). The cyclopentenone ring is essentially planar [maximum deviation from the mean plane = 0.022 (2) Å for C4]. The bonding geometry is very similar to that in cyclotene, (Ib) (Fayle et al., 1998) and other crystallographically characterized cyclopentenones (Ley et al., 1993; Tsuboi et al., 1983). As shown in Fig. 2, the molecules connect into chains by means of intermolecular hydrogen bonds (Table 2).

The molecule in the monoclinic form exists as the same tautomer (IIb) and has two independent molecules in the asymmetric unit (Fig. 3), which differ in the orientation of the hydroxyl H atom. One molecule has the OH group in a s-cis conformation, as in the orthorhombic form, while the other molecule has an S-trans conformation of the OH group, as was found for cyclotene, (Ib) (Fayle et al., 1998). Apart from this difference, the two independent molecules have very similar geometries to one another (Table 3) and to the orthorhombic form. The two unique molecules are connected by a linear hydrogen bond (Table 4). These pairs of molecules further assemble into a puckered ribbon array (Fig. 4) by means of additional hydrogen bonds.

Experimental top

The title compound was prepared by a literature procedure (Acheson, 1956). Crystals of the orthorhombic form of (2) were obtained by low-temperature crystallization (195 K) from a mixture (5:1) of n-hexane and ethyl acetate. Vacuum distillation (351–359 K, 8 m mH g) of (II) furnished crystals of the monoclinic form.

Refinement top

Crystal decay was monitored by the measurement of duplicate reflections. The tautomeric hydroxyl hydrogen atoms were located by difference Fourier calculations and their positions refined. CH H atoms were placed in calculated positions. The absolute configuration of the orthorhombic form could not be determined, as judged by the Flack parameter [−0.4 (18)](Flack, 1983).

Computing details top

For both compounds, data collection: SMART (Siemens 1999); cell refinement: SAINT (Siemens 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Perspective view and atom labelling of the orthorhombic form of (IIb). Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as small circles of arbitrary radii.
[Figure 2] Fig. 2. Packing diagram showing the hydrogen-bonded chains of molecules in the orthorhombic form.
[Figure 3] Fig. 3. Perspective view and atom labelling of the two independent molecules in the monoclinic form of (IIb). Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as small circles of arbitrary radii.
[Figure 4] Fig. 4. Packing diagram showing the hydrogen-bonded ribbons in the monoclinic form.
(3sm1) 3-Hydroxycyclopent-2-enone top
Crystal data top
C5H6O2Dx = 1.363 Mg m3
Mr = 98.10Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1694 reflections
a = 5.370 (5) Åθ = 3.1–25.0°
b = 8.971 (8) ŵ = 0.11 mm1
c = 9.920 (9) ÅT = 163 K
V = 477.9 (8) Å3Plate, colourless
Z = 40.68 × 0.18 × 0.01 mm
F(000) = 208
Data collection top
Siemens SMART CCD
diffractometer
835 independent reflections
Radiation source: fine-focus sealed tube674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.19 pixels mm-1θmax = 25.0°, θmin = 3.1°
Exposures over 0.5° ϕ or ω rotation scansh = 63
Absorption correction: multi-scan
(SADABS; Siemens, 1999)
k = 1010
Tmin = 0.806, Tmax = 0.968l = 1111
5395 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0411P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
835 reflectionsΔρmax = 0.12 e Å3
67 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.4 (18)
Crystal data top
C5H6O2V = 477.9 (8) Å3
Mr = 98.10Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.370 (5) ŵ = 0.11 mm1
b = 8.971 (8) ÅT = 163 K
c = 9.920 (9) Å0.68 × 0.18 × 0.01 mm
Data collection top
Siemens SMART CCD
diffractometer
835 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1999)
674 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 0.968Rint = 0.033
5395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070Δρmax = 0.12 e Å3
S = 0.98Δρmin = 0.16 e Å3
835 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
67 parametersAbsolute structure parameter: 0.4 (18)
0 restraints
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
xyzUiso*/Ueq
O10.4244 (2)0.81562 (13)0.55387 (12)0.0402 (4)
C10.4856 (3)0.92964 (18)0.49219 (18)0.0328 (5)
O20.1665 (2)0.90991 (14)0.31264 (12)0.0390 (4)
H20.127 (4)0.834 (2)0.362 (2)0.047*
C20.3634 (3)0.98241 (19)0.36880 (18)0.0305 (4)
C30.4726 (3)1.10732 (19)0.32288 (19)0.0347 (5)
H30.41911.16070.24540.042*
C40.6891 (4)1.15175 (19)0.40908 (18)0.0376 (5)
H4A0.66711.25420.44420.045*
H4B0.84651.14710.35730.045*
C50.6902 (4)1.03691 (18)0.52556 (18)0.0369 (5)
H5A0.85260.98490.53050.044*
H5B0.65801.08650.61300.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0421 (9)0.0328 (7)0.0457 (8)0.0019 (6)0.0011 (6)0.0106 (6)
C10.0331 (12)0.0292 (9)0.0362 (10)0.0074 (8)0.0038 (9)0.0027 (9)
O20.0459 (9)0.0319 (7)0.0392 (7)0.0053 (7)0.0047 (7)0.0056 (6)
C20.0322 (11)0.0274 (9)0.0317 (9)0.0046 (8)0.0013 (8)0.0043 (8)
C30.0402 (12)0.0291 (10)0.0348 (10)0.0024 (9)0.0034 (9)0.0023 (8)
C40.0426 (13)0.0278 (9)0.0423 (11)0.0000 (10)0.0023 (9)0.0027 (7)
C50.0377 (12)0.0339 (9)0.0390 (11)0.0009 (9)0.0006 (10)0.0000 (8)
Geometric parameters (Å, º) top
O1—C11.236 (2)C3—H30.9500
C1—C21.467 (3)C4—C51.548 (3)
C1—C51.498 (3)C4—H4A0.9900
O2—C21.361 (2)C4—H4B0.9900
O2—H20.87 (2)C5—H5A0.9900
C2—C31.344 (3)C5—H5B0.9900
C3—C41.497 (3)
O1—C1—C2124.13 (17)C3—C4—H4A110.8
O1—C1—C5128.10 (17)C5—C4—H4A110.8
C2—C1—C5107.77 (15)C3—C4—H4B110.8
C2—O2—H2109.6 (13)C5—C4—H4B110.8
C3—C2—O2126.77 (19)H4A—C4—H4B108.9
C3—C2—C1110.90 (18)C1—C5—C4105.05 (15)
O2—C2—C1122.33 (16)C1—C5—H5A110.7
C2—C3—C4111.53 (17)C4—C5—H5A110.7
C2—C3—H3124.2C1—C5—H5B110.7
C4—C3—H3124.2C4—C5—H5B110.7
C3—C4—C5104.61 (15)H5A—C5—H5B108.8
O1—C1—C2—C3178.77 (17)C1—C2—C3—C41.6 (2)
C5—C1—C2—C30.93 (19)C2—C3—C4—C53.40 (19)
O1—C1—C2—O21.2 (3)O1—C1—C5—C4176.75 (17)
C5—C1—C2—O2179.14 (15)C2—C1—C5—C42.93 (18)
O2—C2—C3—C4178.30 (15)C3—C4—C5—C13.72 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.87 (2)1.92 (2)2.745 (2)159.5 (18)
Symmetry code: (i) x1/2, y+3/2, z+1.
(3sm2) 3-Hydroxycyclopent-2-enone top
Crystal data top
C5H6O2F(000) = 416
Mr = 98.10Dx = 1.371 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.100 (7) ÅCell parameters from 1577 reflections
b = 10.761 (8) Åθ = 2.7–25.0°
c = 10.124 (7) ŵ = 0.11 mm1
β = 106.491 (11)°T = 163 K
V = 950.6 (12) Å3Plate, colourless
Z = 80.45 × 0.18 × 0.03 mm
Data collection top
Siemens SMART CCD
diffractometer
1669 independent reflections
Radiation source: fine-focus sealed tube973 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
Detector resolution: 8.19 pixels mm-1θmax = 25.0°, θmin = 2.7°
Exposures over 0.5° ϕ or ω rotation scansh = 1010
Absorption correction: multi-scan
(SADABS; Siemens, 1999)
k = 812
Tmin = 0.838, Tmax = 0.968l = 1212
10377 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0639P)2]
where P = (Fo2 + 2Fc2)/3
1669 reflections(Δ/σ)max = 0.001
133 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C5H6O2V = 950.6 (12) Å3
Mr = 98.10Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.100 (7) ŵ = 0.11 mm1
b = 10.761 (8) ÅT = 163 K
c = 10.124 (7) Å0.45 × 0.18 × 0.03 mm
β = 106.491 (11)°
Data collection top
Siemens SMART CCD
diffractometer
1669 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1999)
973 reflections with I > 2σ(I)
Tmin = 0.838, Tmax = 0.968Rint = 0.059
10377 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.20 e Å3
1669 reflectionsΔρmin = 0.23 e Å3
133 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
xyzUiso*/Ueq
O10.01294 (19)0.97162 (14)0.31624 (18)0.0394 (5)
C10.0384 (3)0.8592 (2)0.3039 (2)0.0279 (6)
O20.30962 (19)0.88026 (14)0.18963 (17)0.0324 (5)
H20.400 (3)0.841 (2)0.165 (2)0.039*
C20.1883 (3)0.8033 (2)0.2408 (2)0.0248 (6)
C30.1780 (3)0.6789 (2)0.2446 (2)0.0288 (6)
H3A0.26200.62440.20870.035*
C40.0173 (3)0.6368 (2)0.3125 (3)0.0314 (6)
H4A0.02150.58510.24870.038*
H4B0.01270.58760.39620.038*
C50.0774 (3)0.7567 (2)0.3499 (2)0.0299 (6)
H5A0.12730.76130.45030.036*
H5B0.15710.76120.30090.036*
O1'0.07451 (18)1.24911 (14)0.38355 (16)0.0346 (5)
C1'0.2140 (3)1.2611 (2)0.4336 (2)0.0243 (5)
O2'0.2776 (2)1.03840 (14)0.44591 (19)0.0411 (5)
H2'0.173 (3)1.029 (2)0.399 (3)0.049*
C2'0.3226 (3)1.1582 (2)0.4693 (2)0.0285 (6)
C3'0.4651 (3)1.1992 (2)0.5248 (2)0.0315 (6)
H3'A0.55201.14660.55510.038*
C4'0.4717 (3)1.3385 (2)0.5337 (3)0.0320 (6)
H4'A0.54081.37250.48280.038*
H4'B0.50771.36630.63080.038*
C5'0.3046 (3)1.3794 (2)0.4666 (2)0.0288 (6)
H5'A0.26691.43110.53110.035*
H5'B0.29661.42780.38170.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0394 (11)0.0174 (11)0.0576 (12)0.0065 (8)0.0076 (9)0.0000 (8)
C10.0339 (16)0.0253 (15)0.0252 (14)0.0021 (11)0.0098 (12)0.0017 (10)
O20.0289 (10)0.0195 (10)0.0452 (11)0.0017 (8)0.0046 (9)0.0020 (8)
C20.0273 (14)0.0214 (14)0.0253 (14)0.0002 (11)0.0069 (11)0.0023 (10)
C30.0335 (15)0.0214 (15)0.0310 (14)0.0059 (11)0.0083 (12)0.0003 (11)
C40.0394 (16)0.0183 (14)0.0382 (15)0.0007 (11)0.0138 (13)0.0034 (11)
C50.0289 (14)0.0270 (14)0.0332 (13)0.0005 (11)0.0081 (11)0.0041 (11)
O1'0.0318 (11)0.0238 (10)0.0459 (11)0.0041 (8)0.0072 (8)0.0027 (8)
C1'0.0260 (14)0.0218 (14)0.0255 (13)0.0007 (11)0.0078 (11)0.0000 (11)
O2'0.0313 (11)0.0136 (10)0.0726 (14)0.0014 (8)0.0050 (10)0.0044 (8)
C2'0.0304 (15)0.0195 (14)0.0346 (15)0.0000 (11)0.0078 (12)0.0017 (10)
C3'0.0321 (16)0.0230 (14)0.0395 (16)0.0026 (11)0.0100 (12)0.0012 (11)
C4'0.0386 (16)0.0223 (14)0.0369 (15)0.0070 (11)0.0135 (13)0.0038 (11)
C5'0.0368 (15)0.0179 (13)0.0346 (15)0.0019 (11)0.0146 (12)0.0024 (10)
Geometric parameters (Å, º) top
O1—C11.231 (3)O1'—C1'1.232 (3)
C1—C21.461 (3)C1'—C2'1.460 (3)
C1—C51.505 (3)C1'—C5'1.502 (3)
O2—C21.360 (3)O2'—C2'1.353 (3)
O2—H20.89 (2)O2'—H2'0.94 (3)
C2—C31.341 (3)C2'—C3'1.333 (3)
C3—C41.499 (3)C3'—C4'1.502 (3)
C3—H3A0.9500C3'—H3'A0.9500
C4—C51.538 (3)C4'—C5'1.543 (3)
C4—H4A0.9900C4'—H4'A0.9900
C4—H4B0.9900C4'—H4'B0.9900
C5—H5A0.9900C5'—H5'A0.9900
C5—H5B0.9900C5'—H5'B0.9900
O1—C1—C2125.1 (2)O1'—C1'—C2'124.6 (2)
O1—C1—C5126.4 (2)O1'—C1'—C5'128.1 (2)
C2—C1—C5108.5 (2)C2'—C1'—C5'107.3 (2)
C2—O2—H2113.9 (15)C2'—O2'—H2'113.5 (15)
C3—C2—O2131.4 (2)C3'—C2'—O2'126.8 (2)
C3—C2—C1110.5 (2)C3'—C2'—C1'111.3 (2)
O2—C2—C1118.1 (2)O2'—C2'—C1'121.9 (2)
C2—C3—C4111.5 (2)C2'—C3'—C4'111.9 (2)
C2—C3—H3A124.3C2'—C3'—H3'A124.0
C4—C3—H3A124.3C4'—C3'—H3'A124.0
C3—C4—C5105.34 (18)C3'—C4'—C5'103.92 (18)
C3—C4—H4A110.7C3'—C4'—H4'A111.0
C5—C4—H4A110.7C5'—C4'—H4'A111.0
C3—C4—H4B110.7C3'—C4'—H4'B111.0
C5—C4—H4B110.7C5'—C4'—H4'B111.0
H4A—C4—H4B108.8H4'A—C4'—H4'B109.0
C1—C5—C4104.17 (19)C1'—C5'—C4'105.47 (18)
C1—C5—H5A110.9C1'—C5'—H5'A110.6
C4—C5—H5A110.9C4'—C5'—H5'A110.6
C1—C5—H5B110.9C1'—C5'—H5'B110.6
C4—C5—H5B110.9C4'—C5'—H5'B110.6
H5A—C5—H5B108.9H5'A—C5'—H5'B108.8
O1—C1—C2—C3179.4 (2)O1'—C1'—C2'—C3'178.4 (2)
C5—C1—C2—C30.8 (3)C5'—C1'—C2'—C3'2.7 (3)
O1—C1—C2—O21.0 (3)O1'—C1'—C2'—O2'1.9 (4)
C5—C1—C2—O2178.84 (19)C5'—C1'—C2'—O2'177.0 (2)
O2—C2—C3—C4179.9 (2)O2'—C2'—C3'—C4'179.5 (2)
C1—C2—C3—C40.3 (3)C1'—C2'—C3'—C4'0.2 (3)
C2—C3—C4—C51.3 (3)C2'—C3'—C4'—C5'2.4 (3)
O1—C1—C5—C4178.7 (2)O1'—C1'—C5'—C4'177.2 (2)
C2—C1—C5—C41.5 (2)C2'—C1'—C5'—C4'4.0 (2)
C3—C4—C5—C11.6 (2)C3'—C4'—C5'—C1'3.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.94 (3)1.77 (3)2.694 (3)165 (2)
O2—H2···O1i0.89 (2)1.82 (2)2.709 (3)175 (2)
Symmetry code: (i) x1/2, y1/2, z+1/2.

Experimental details

(3sm1)(3sm2)
Crystal data
Chemical formulaC5H6O2C5H6O2
Mr98.1098.10
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/n
Temperature (K)163163
a, b, c (Å)5.370 (5), 8.971 (8), 9.920 (9)9.100 (7), 10.761 (8), 10.124 (7)
α, β, γ (°)90, 90, 9090, 106.491 (11), 90
V3)477.9 (8)950.6 (12)
Z48
Radiation typeMo KαMo Kα
µ (mm1)0.110.11
Crystal size (mm)0.68 × 0.18 × 0.010.45 × 0.18 × 0.03
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Siemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Siemens, 1999)
Multi-scan
(SADABS; Siemens, 1999)
Tmin, Tmax0.806, 0.9680.838, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
5395, 835, 674 10377, 1669, 973
Rint0.0330.059
(sin θ/λ)max1)0.5940.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.070, 0.98 0.043, 0.115, 0.91
No. of reflections8351669
No. of parameters67133
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.160.20, 0.23
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter0.4 (18)?

Computer programs: SMART (Siemens 1999), SAINT (Siemens 1999), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97.

Selected geometric parameters (Å, º) for (3sm1) top
O1—C11.236 (2)O2—H20.87 (2)
C1—C21.467 (3)C2—C31.344 (3)
C1—C51.498 (3)C3—C41.497 (3)
O2—C21.361 (2)C4—C51.548 (3)
O1—C1—C2124.13 (17)C3—C2—C1110.90 (18)
O1—C1—C5128.10 (17)O2—C2—C1122.33 (16)
C2—C1—C5107.77 (15)C2—C3—C4111.53 (17)
C2—O2—H2109.6 (13)C3—C4—C5104.61 (15)
C3—C2—O2126.77 (19)C1—C5—C4105.05 (15)
Hydrogen-bond geometry (Å, º) for (3sm1) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.87 (2)1.92 (2)2.745 (2)159.5 (18)
Symmetry code: (i) x1/2, y+3/2, z+1.
Selected geometric parameters (Å, º) for (3sm2) top
O1—C11.231 (3)O1'—C1'1.232 (3)
C1—C21.461 (3)C1'—C2'1.460 (3)
C1—C51.505 (3)C1'—C5'1.502 (3)
O2—C21.360 (3)O2'—C2'1.353 (3)
O2—H20.89 (2)O2'—H2'0.94 (3)
C2—C31.341 (3)C2'—C3'1.333 (3)
C3—C41.499 (3)C3'—C4'1.502 (3)
C4—C51.538 (3)C4'—C5'1.543 (3)
O1—C1—C2125.1 (2)O1'—C1'—C2'124.6 (2)
O1—C1—C5126.4 (2)O1'—C1'—C5'128.1 (2)
C2—C1—C5108.5 (2)C2'—C1'—C5'107.3 (2)
C2—O2—H2113.9 (15)C2'—O2'—H2'113.5 (15)
C3—C2—O2131.4 (2)C3'—C2'—O2'126.8 (2)
C3—C2—C1110.5 (2)C3'—C2'—C1'111.3 (2)
O2—C2—C1118.1 (2)O2'—C2'—C1'121.9 (2)
C2—C3—C4111.5 (2)C2'—C3'—C4'111.9 (2)
C3—C4—C5105.34 (18)C3'—C4'—C5'103.92 (18)
C1—C5—C4104.17 (19)C1'—C5'—C4'105.47 (18)
Hydrogen-bond geometry (Å, º) for (3sm2) top
D—H···AD—HH···AD···AD—H···A
O2'—H2'···O10.94 (3)1.77 (3)2.694 (3)165 (2)
O2—H2···O1'i0.89 (2)1.82 (2)2.709 (3)175 (2)
Symmetry code: (i) x1/2, y1/2, z+1/2.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds