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Acta Cryst. (2006). C62, o178-o181
https://doi.org/10.1107/S0108270106005063
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C[triple bond]C—H systems as hydrogen-bond donors and acceptors: trans-1,2-diethynylcyclo­hexane-1,2-diol and trans-1,4-diprop-2-ynylcyclo­hexane-1,4-diol monohydrate

U. Hamann, J. Kämpen, P. Bubenitschek, H. Hopf and P. G. Jones
The title 1,2-diol derivative, C10H12O2, crystallizes with two independent but closely similar mol­ecules in the asymmetric unit. Only two of the four OH groups are involved in classical hydrogen bonding; the mol­ecules thereby associate to form chains parallel to the short c axis. The other two OH groups are involved in O—H...(C[triple bond]C) systems. Additionally, three of the four C[triple bond]C—H groups act as donors in C—H...O inter­actions. The 1,4-diol derivative crystallizes with two independent half-mol­ecules of the diol (each associated with an inversion centre) and one water mol­ecule in the asymmetric unit, C12H16O2·H2O. Both OH groups and one water H atom act as classical hydrogen-bond donors, leading to layers parallel to the ac plane. The second water H atom is involved in a three-centre contact to two C[triple bond]C bonds. One acetyl­enic H atom makes a very short `weak' hydrogen bond to a hydr­oxy O atom, and the other is part of a three-centre system in which the acceptors are a hydroxy O atom and a C[triple bond]C bond.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106005063/ln3003sup1.cif
Contains datablocks II, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005063/ln3003IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005063/ln3003IVsup3.hkl
Contains datablock IV

CCDC references: 605682; 605683

Comment top

The title compounds, (II) and (IV), respectively, are related trans-cyclohexane-1,2-diols that we have used as synthetic intermediates. Compound (II) is a long-known (Ried & Schmidt, 1957) bis-propargylic diol that we used in our studies (Eshdat et al., 2002) of novel cross-conjugated enynes. Similarly, compound (IV) is a known (Cognacq et al., 1967) compound that we used in our studies of semicyclic olefins and allenes (Hopf et al., 2002). The structures of both compounds were confirmed by X-ray crystal structure determination and proved to display a variety of secondary contacts, not only the expected classical hydrogen bonds but also interactions involving the C≡C—H moieties.

Compound (II) crystallizes with two independent molecules in the asymmetric unit, which are closely similar (a least-squares fit of all non-H atoms gives an r.m.s. deviation of 0.044 Å). The hydroxy groups occupy equatorial and the propargyl groups the axial positions of the cyclohexyl rings (Fig. 1). Primes indicate atoms of the second molecule, which is inverted with respect to the first in the coordinates chosen for the asymmetric unit [to give a hydrogen bond (see below) between both independent molecules without transformation]. The one major difference lies in the configuration of the OH groups, whereby C1'—C2'—O2'—H02' is a trans-periplanar group [the O—H bond is parallel to the C1'—C2' ring bond, torsion angle -177 (2)°] and all other analogous groups are gauche; the corresponding torsion angles (all involving the ring bonds C1—C2 or C1'—C2') involving atoms H01, H01' and H02 are 72 (2), -77 (2) and 76 (2)°, respectively. The molecular dimensions may be regarded as normal. The rings display the usual chair form [absolute torsion angles 54.4 (2)–57.8 (2)°].

The molecular packing of (II) is puzzling at first sight. The molecules associate via two classical hydrogen bonds (Table 2) involving O2—H02 and O2'—H02' as donors, to form chains of graph set C22(7) (Etter, 1990) parallel to the short c axis (Fig. 2; neighbouring chains define layers parallel to the ac plane). However, O1—H01 and O1'—H01' do not take part in such interactions. Closer inspection shows that these OH groups form `weak' intermolecular hydrogen bonds (Desiraju & Steiner, 1999) to the alkyne triple bonds, with both interactions being within the asymmetric unit: O1—H01···midpoint(C9'≡C10'), H···acceptor 2.60 Å and angle 162°; O1'—H01'···midpoint(C9≡C10), H···acceptor 2.71 Å and angle 111°. The latter interaction is admittedly a borderline case in view of its narrow angle.

Acetylenic H atoms represent a fairly acidic form of CH group and can also act as hydrogen-bond donors (Desiraju & Steiner, 1999); as a concrete example, we have drawn attention to C≡C—H···Cl—Au interactions (Bardají et al., 2002). In the current structure, three of the four C≡C—H groups act in this way (Table 2) to connect the classical hydrogen-bonded layers in the third dimension parallel to the long b axis (Fig. 3).

All four O atoms are thus topologically different as regards their hydrogen-bonding behaviour, which may be summarized as follows (D = donor, A = acceptor, C = classical, W = `weak'): O1 WD,WA; O2 CD,CA,WA; O3 CA,WD; O4 CD,WA. One might speculate that the `extra' interaction for atom O2 is connected with its different C—C—O—H torsion angle (see above).

Compound (IV) also crystallizes with two symmetry-independent molecules, which, however, display inversion symmetry [molecule 1 about (1, 1/2, 1) and molecule 2 about (1/2, 1/2, 1/2)] (Fig. 4). A least-squares fit of the ring atoms of the asymmetric unit gives an r.m.s. deviation of 0.07 Å. As in (II), the OH groups of the two molecules are oriented differently; in molecule 2, the C2'—C1'—O1'—H01' torsion angle is 42 (1)° and the OH group is very approximately parallel to the propargyl group (see Fig. 4, bottom left), whereas in molecule 1 the corresponding angle is 171 (1)° and the corresponding groups point in widely disparate directions. The asymmetric unit also contains a molecule of water, which was presumably absorbed from the atmosphere during the slow crystallization of the oily product. In contrast with (II), the hydroxy groups are axial and the propynyl groups equatorial.

The contribution of classical hydrogen bonds to the packing of (IV) is shown in Fig. 5. Both independent OH groups and one water H atom, H03, act as hydrogen-bond donors (Table 4; for a discussion of atom H04, see below) and the overall effect is to form a layer structure parallel to the ac plane. The two independent rings thus formed are both of graph set R66(22).

The second water H atom, H04, appears at first sight to make no significant contacts at all. However, it projects away from the layer shown in Fig. 5 and makes contacts of 3.03 and 3.04 Å (angles at H04: 114 and 157°, respectively) to the midpoints of the triple bonds C5≡C6 and C5'≡C6' in the neighbouring layer at (x, 1 + y, z) (Fig. 6a). For a three-centre contact, these very long distances may still indicate a significant interaction.

The acetylenic H atom, H6, of (IV) makes a short (2.37 Å) `weak' hydrogen bond with atom O1' in the neighbouring layer at (x, -1 + y, z). The corresponding contact from atom H6' to atom O1 is, however, very long and bent (Table 4); again, the explanation may be sought in a three-centre interaction, the other branch of which is a C—H···π interaction to the midpoint of C5≡C6 (2.74 Å and 166°). The operator is (-1 + x, y, z) for both branches, so that the system forms part of the layer structure, but this is not easy to recognize in Fig. 5; it is depicted for clarity in Fig. 6(b).

Experimental top

The diol (II) was prepared from 1,2-cyclohexanedione (1) by reaction with sodium acetylide, as described by Ried & Schmidt (1957). The spectroscopic data (Hamann, 1992) were consistent with literature values. Single crystals were obtained from benzene–petroleum ether (Ratio?). Diol (IV) was prepared from 1,4-cyclohexanedione (3) and propargyl bromide, as described by Cognacq et al. (1967). It formed an oil that crystallized slowly. Analytical and spectroscopic data agree with those of the original reference.

Refinement top

Methylene H atoms were included in calculated positions and refined using a riding model, with fixed C—H bond lengths of 0.99 Å and with Uiso(H) = 1.2Ueq(C). Other H atoms were located in difference syntheses and refined freely, but with C—H (acetylenic) and O—H bond distances each restrained to be equal within a notional s.u. of 0.02 Å.

Structure description top

The title compounds, (II) and (IV), respectively, are related trans-cyclohexane-1,2-diols that we have used as synthetic intermediates. Compound (II) is a long-known (Ried & Schmidt, 1957) bis-propargylic diol that we used in our studies (Eshdat et al., 2002) of novel cross-conjugated enynes. Similarly, compound (IV) is a known (Cognacq et al., 1967) compound that we used in our studies of semicyclic olefins and allenes (Hopf et al., 2002). The structures of both compounds were confirmed by X-ray crystal structure determination and proved to display a variety of secondary contacts, not only the expected classical hydrogen bonds but also interactions involving the C≡C—H moieties.

Compound (II) crystallizes with two independent molecules in the asymmetric unit, which are closely similar (a least-squares fit of all non-H atoms gives an r.m.s. deviation of 0.044 Å). The hydroxy groups occupy equatorial and the propargyl groups the axial positions of the cyclohexyl rings (Fig. 1). Primes indicate atoms of the second molecule, which is inverted with respect to the first in the coordinates chosen for the asymmetric unit [to give a hydrogen bond (see below) between both independent molecules without transformation]. The one major difference lies in the configuration of the OH groups, whereby C1'—C2'—O2'—H02' is a trans-periplanar group [the O—H bond is parallel to the C1'—C2' ring bond, torsion angle -177 (2)°] and all other analogous groups are gauche; the corresponding torsion angles (all involving the ring bonds C1—C2 or C1'—C2') involving atoms H01, H01' and H02 are 72 (2), -77 (2) and 76 (2)°, respectively. The molecular dimensions may be regarded as normal. The rings display the usual chair form [absolute torsion angles 54.4 (2)–57.8 (2)°].

The molecular packing of (II) is puzzling at first sight. The molecules associate via two classical hydrogen bonds (Table 2) involving O2—H02 and O2'—H02' as donors, to form chains of graph set C22(7) (Etter, 1990) parallel to the short c axis (Fig. 2; neighbouring chains define layers parallel to the ac plane). However, O1—H01 and O1'—H01' do not take part in such interactions. Closer inspection shows that these OH groups form `weak' intermolecular hydrogen bonds (Desiraju & Steiner, 1999) to the alkyne triple bonds, with both interactions being within the asymmetric unit: O1—H01···midpoint(C9'≡C10'), H···acceptor 2.60 Å and angle 162°; O1'—H01'···midpoint(C9≡C10), H···acceptor 2.71 Å and angle 111°. The latter interaction is admittedly a borderline case in view of its narrow angle.

Acetylenic H atoms represent a fairly acidic form of CH group and can also act as hydrogen-bond donors (Desiraju & Steiner, 1999); as a concrete example, we have drawn attention to C≡C—H···Cl—Au interactions (Bardají et al., 2002). In the current structure, three of the four C≡C—H groups act in this way (Table 2) to connect the classical hydrogen-bonded layers in the third dimension parallel to the long b axis (Fig. 3).

All four O atoms are thus topologically different as regards their hydrogen-bonding behaviour, which may be summarized as follows (D = donor, A = acceptor, C = classical, W = `weak'): O1 WD,WA; O2 CD,CA,WA; O3 CA,WD; O4 CD,WA. One might speculate that the `extra' interaction for atom O2 is connected with its different C—C—O—H torsion angle (see above).

Compound (IV) also crystallizes with two symmetry-independent molecules, which, however, display inversion symmetry [molecule 1 about (1, 1/2, 1) and molecule 2 about (1/2, 1/2, 1/2)] (Fig. 4). A least-squares fit of the ring atoms of the asymmetric unit gives an r.m.s. deviation of 0.07 Å. As in (II), the OH groups of the two molecules are oriented differently; in molecule 2, the C2'—C1'—O1'—H01' torsion angle is 42 (1)° and the OH group is very approximately parallel to the propargyl group (see Fig. 4, bottom left), whereas in molecule 1 the corresponding angle is 171 (1)° and the corresponding groups point in widely disparate directions. The asymmetric unit also contains a molecule of water, which was presumably absorbed from the atmosphere during the slow crystallization of the oily product. In contrast with (II), the hydroxy groups are axial and the propynyl groups equatorial.

The contribution of classical hydrogen bonds to the packing of (IV) is shown in Fig. 5. Both independent OH groups and one water H atom, H03, act as hydrogen-bond donors (Table 4; for a discussion of atom H04, see below) and the overall effect is to form a layer structure parallel to the ac plane. The two independent rings thus formed are both of graph set R66(22).

The second water H atom, H04, appears at first sight to make no significant contacts at all. However, it projects away from the layer shown in Fig. 5 and makes contacts of 3.03 and 3.04 Å (angles at H04: 114 and 157°, respectively) to the midpoints of the triple bonds C5≡C6 and C5'≡C6' in the neighbouring layer at (x, 1 + y, z) (Fig. 6a). For a three-centre contact, these very long distances may still indicate a significant interaction.

The acetylenic H atom, H6, of (IV) makes a short (2.37 Å) `weak' hydrogen bond with atom O1' in the neighbouring layer at (x, -1 + y, z). The corresponding contact from atom H6' to atom O1 is, however, very long and bent (Table 4); again, the explanation may be sought in a three-centre interaction, the other branch of which is a C—H···π interaction to the midpoint of C5≡C6 (2.74 Å and 166°). The operator is (-1 + x, y, z) for both branches, so that the system forms part of the layer structure, but this is not easy to recognize in Fig. 5; it is depicted for clarity in Fig. 6(b).

Computing details top

For both compounds, data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The two independent molecules of compound (II) in the crystal. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Heavy dashed lines indicate classical hydrogen bonds within the asymmetric unit, and thin dashed lines indicate `weak' O—H···(C≡C) interactions (see text).
[Figure 2] Fig. 2. A packing diagram for compound (II), viewed parallel to the b axis, showing the classical hydrogen bonds forming chains of molecules parallel to the c axis in the region b ≈ 1/8. Bonds of the second independent molecule are drawn thinner. H atoms other than those of hydroxy groups have been omitted.
[Figure 3] Fig. 3. A packing diagram for compound (II), viewed parallel to the a axis, showing the 'weak' hydrogen bonds (dashed lines) between the molecular chains. Bonds of the second independent molecule are drawn thinner.
[Figure 4] Fig. 4. The structure of compound (IV) in the crystal. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Only the asymmetric unit is numbered. Heavy dashed lines represent classical hydrogen bonds within the asymmetric unit.
[Figure 5] Fig. 5. A packing diagram of compound (IV). Classical hydrogen bonds are indicated by thin dashed lines. Bonds of the second independent molecule are drawn thinner. H atoms other than those of hydroxy groups and water have been omitted.
[Figure 6] Fig. 6. The packing of compound (II) [(IV?)]. (a) The environment of the water atom H04. (b) The environment of the acetylenic atom H6'. For details see text. [Symmetry codes: (#) x, 1 + y, z; (*) -1 + x, y, z.]
(II) trans-1,2-Diethynylcyclohexane-1,2-diol top
Crystal data top
C10H12O2F(000) = 704
Mr = 164.20Dx = 1.235 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.563 (3) ÅCell parameters from 46 reflections
b = 23.839 (6) Åθ = 8.5–11.5°
c = 7.025 (2) ŵ = 0.09 mm−1
β = 93.46 (2)°T = 153 K
V = 1765.8 (8) Å3Prism, colourless
Z = 80.45 × 0.40 × 0.40 mm
Data collection top
Stoe STADI-4
diffractometer		Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.0°
Graphite monochromatorh = −12→11
ω/θ scansk = −28→9
4400 measured reflectionsl = −8→8
3131 independent reflections3 standard reflections every 60 min
2380 reflections with I > 2σ(I) intensity decay: none
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)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0332P)2 + 0.7551P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3131 reflectionsΔρmax = 0.18 e Å−3
250 parametersΔρmin = −0.18 e Å−3
12 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0080 (10)
Crystal data top
C10H12O2V = 1765.8 (8) Å3
Mr = 164.20Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.563 (3) ŵ = 0.09 mm−1
b = 23.839 (6) ÅT = 153 K
c = 7.025 (2) Å0.45 × 0.40 × 0.40 mm
β = 93.46 (2)°
Data collection top
Stoe STADI-4
diffractometer		Rint = 0.028
4400 measured reflections3 standard reflections every 60 min
3131 independent reflections intensity decay: none
2380 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.04512 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.18 e Å−3
3131 reflectionsΔρmin = −0.18 e Å−3
250 parameters
Special details top

Experimental. 1,1-Diphenyl-2,2-bis(trimethylsilylethynyl)ethene

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
C10.83692 (18)0.62268 (8)0.3713 (3)0.0236 (4)
C20.74653 (17)0.60275 (7)0.5244 (3)0.0204 (4)
C30.81572 (19)0.60515 (8)0.7221 (3)0.0266 (4)
H3A0.83840.64450.75300.032*
H3B0.75830.59160.81860.032*
C40.93575 (19)0.56940 (9)0.7314 (3)0.0324 (5)
H4A0.98030.57350.85870.039*
H4B0.91250.52940.71360.039*
C51.02384 (19)0.58691 (9)0.5787 (3)0.0347 (5)
H5A1.09740.56110.58100.042*
H5B1.05610.62520.60660.042*
C60.95592 (18)0.58596 (9)0.3813 (3)0.0293 (5)
H6A0.93190.54690.34800.035*
H6B1.01450.59940.28640.035*
C70.86975 (18)0.68239 (8)0.4052 (3)0.0267 (4)
C80.8953 (2)0.73001 (10)0.4312 (3)0.0384 (5)
H80.916 (3)0.7683 (8)0.458 (4)0.063 (8)*
C90.70117 (17)0.54546 (8)0.4804 (3)0.0229 (4)
C100.6578 (2)0.50046 (9)0.4479 (3)0.0318 (5)
H100.622 (2)0.4647 (9)0.419 (4)0.064 (8)*
O10.77933 (14)0.61563 (6)0.18327 (18)0.0299 (4)
H010.724 (2)0.6401 (9)0.171 (4)0.049 (8)*
O20.63907 (12)0.63975 (6)0.52862 (19)0.0239 (3)
H020.593 (2)0.6317 (11)0.433 (3)0.058 (8)*
C1'0.37595 (17)0.61074 (8)0.1025 (3)0.0226 (4)
C2'0.43125 (17)0.64112 (8)−0.0689 (3)0.0238 (4)
C3'0.32330 (19)0.66407 (8)−0.2016 (3)0.0299 (5)
H3'10.35970.6856−0.30560.036*
H3'20.27470.6323−0.25990.036*
C4'0.2336 (2)0.70171 (9)−0.0983 (3)0.0359 (5)
H4'10.27930.7360−0.05390.043*
H4'20.16240.7132−0.18790.043*
C5'0.1817 (2)0.67186 (9)0.0713 (3)0.0342 (5)
H5'10.12700.64030.02560.041*
H5'20.12900.69820.14130.041*
C6'0.28866 (19)0.64962 (8)0.2053 (3)0.0286 (5)
H6'10.33840.68150.26030.034*
H6'20.25220.62910.31160.034*
C7'0.30831 (19)0.55942 (8)0.0360 (3)0.0258 (4)
C8'0.2575 (2)0.51775 (9)−0.0130 (3)0.0342 (5)
H8'0.221 (2)0.4837 (8)−0.056 (3)0.045 (7)*
C9'0.51511 (19)0.68756 (8)0.0020 (3)0.0285 (5)
C10'0.5809 (2)0.72564 (9)0.0496 (3)0.0375 (5)
H10'0.627 (2)0.7584 (9)0.084 (4)0.069 (9)*
O1'0.47707 (13)0.59540 (6)0.2389 (2)0.0308 (4)
H01'0.513 (2)0.5674 (9)0.197 (4)0.059 (9)*
O2'0.50258 (14)0.60008 (6)−0.1628 (2)0.0314 (4)
H02'0.535 (2)0.6170 (10)−0.251 (3)0.060 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (10)0.0260 (10)0.0209 (9)−0.0010 (8)0.0010 (8)−0.0004 (8)
C20.0177 (9)0.0215 (9)0.0217 (9)0.0019 (8)−0.0001 (7)−0.0014 (8)
C30.0281 (11)0.0319 (11)0.0195 (9)−0.0012 (9)−0.0023 (8)−0.0003 (8)
C40.0267 (11)0.0371 (12)0.0322 (11)0.0016 (9)−0.0081 (9)0.0028 (9)
C50.0209 (11)0.0371 (12)0.0453 (13)0.0040 (9)−0.0033 (9)0.0026 (10)
C60.0231 (11)0.0321 (11)0.0333 (11)0.0004 (9)0.0066 (9)−0.0008 (9)
C70.0234 (10)0.0290 (11)0.0278 (10)−0.0013 (9)0.0018 (8)0.0033 (9)
C80.0396 (13)0.0291 (13)0.0461 (13)−0.0084 (10)−0.0003 (10)0.0014 (10)
C90.0187 (9)0.0273 (11)0.0228 (9)0.0024 (8)0.0010 (8)0.0013 (8)
C100.0268 (11)0.0263 (11)0.0427 (13)−0.0023 (9)0.0057 (10)−0.0024 (10)
O10.0325 (8)0.0375 (9)0.0195 (7)0.0018 (7)0.0004 (6)−0.0016 (6)
O20.0185 (7)0.0281 (7)0.0250 (7)0.0044 (6)−0.0006 (6)−0.0021 (6)
C1'0.0205 (9)0.0252 (10)0.0216 (9)−0.0035 (8)−0.0040 (7)0.0014 (8)
C2'0.0197 (9)0.0253 (10)0.0265 (10)−0.0021 (8)0.0013 (8)−0.0009 (8)
C3'0.0315 (12)0.0308 (11)0.0268 (11)−0.0044 (9)−0.0018 (9)0.0069 (9)
C4'0.0303 (12)0.0306 (11)0.0459 (13)0.0030 (9)−0.0058 (10)0.0079 (10)
C5'0.0247 (11)0.0347 (12)0.0433 (12)0.0041 (9)0.0022 (9)−0.0037 (10)
C6'0.0276 (11)0.0318 (11)0.0269 (10)−0.0037 (9)0.0051 (8)−0.0036 (9)
C7'0.0276 (11)0.0271 (11)0.0227 (10)−0.0029 (9)0.0005 (8)0.0042 (8)
C8'0.0432 (13)0.0308 (12)0.0284 (11)−0.0130 (11)0.0003 (10)0.0024 (9)
C9'0.0233 (10)0.0300 (11)0.0323 (11)−0.0028 (9)0.0028 (9)0.0022 (9)
C10'0.0322 (12)0.0319 (12)0.0484 (14)−0.0089 (10)0.0022 (10)−0.0015 (10)
O1'0.0284 (8)0.0325 (9)0.0301 (8)−0.0013 (7)−0.0106 (6)0.0028 (7)
O2'0.0316 (8)0.0297 (8)0.0343 (8)0.0003 (6)0.0127 (7)−0.0025 (7)
Geometric parameters (Å, º) top
C1—O11.430 (2)C1'—O1'1.438 (2)
C1—C71.481 (3)C1'—C7'1.478 (3)
C1—C61.530 (3)C1'—C6'1.520 (3)
C1—C21.555 (3)C1'—C2'1.549 (3)
C2—O21.439 (2)C2'—O2'1.422 (2)
C2—C91.474 (3)C2'—C9'1.485 (3)
C2—C31.531 (3)C2'—C3'1.530 (3)
C3—C41.526 (3)C3'—C4'1.521 (3)
C3—H3A0.9900C3'—H3'10.9900
C3—H3B0.9900C3'—H3'20.9900
C4—C51.520 (3)C4'—C5'1.519 (3)
C4—H4A0.9900C4'—H4'10.9900
C4—H4B0.9900C4'—H4'20.9900
C5—C61.523 (3)C5'—C6'1.522 (3)
C5—H5A0.9900C5'—H5'10.9900
C5—H5B0.9900C5'—H5'20.9900
C6—H6A0.9900C6'—H6'10.9900
C6—H6B0.9900C6'—H6'20.9900
C7—C81.178 (3)C7'—C8'1.171 (3)
C8—H80.954 (18)C8'—H8'0.940 (17)
C9—C101.183 (3)C9'—C10'1.179 (3)
C10—H100.950 (18)C10'—H10'0.944 (18)
O1—H010.829 (18)O1'—H01'0.832 (19)
O2—H020.828 (19)O2'—H02'0.832 (19)
O1—C1—C7110.12 (15)O1'—C1'—C7'108.99 (15)
O1—C1—C6106.12 (15)O1'—C1'—C6'106.61 (15)
C7—C1—C6111.03 (16)C7'—C1'—C6'111.05 (16)
O1—C1—C2110.98 (15)O1'—C1'—C2'109.68 (15)
C7—C1—C2109.26 (15)C7'—C1'—C2'109.82 (15)
C6—C1—C2109.30 (15)C6'—C1'—C2'110.61 (15)
O2—C2—C9108.99 (15)O2'—C2'—C9'110.29 (15)
O2—C2—C3106.99 (14)O2'—C2'—C3'111.08 (16)
C9—C2—C3110.86 (15)C9'—C2'—C3'110.21 (16)
O2—C2—C1110.19 (14)O2'—C2'—C1'105.92 (15)
C9—C2—C1110.08 (15)C9'—C2'—C1'109.46 (16)
C3—C2—C1109.67 (15)C3'—C2'—C1'109.79 (15)
C4—C3—C2111.60 (16)C4'—C3'—C2'112.54 (16)
C4—C3—H3A109.3C4'—C3'—H3'1109.1
C2—C3—H3A109.3C2'—C3'—H3'1109.1
C4—C3—H3B109.3C4'—C3'—H3'2109.1
C2—C3—H3B109.3C2'—C3'—H3'2109.1
H3A—C3—H3B108.0H3'1—C3'—H3'2107.8
C5—C4—C3111.02 (17)C5'—C4'—C3'111.27 (17)
C5—C4—H4A109.4C5'—C4'—H4'1109.4
C3—C4—H4A109.4C3'—C4'—H4'1109.4
C5—C4—H4B109.4C5'—C4'—H4'2109.4
C3—C4—H4B109.4C3'—C4'—H4'2109.4
H4A—C4—H4B108.0H4'1—C4'—H4'2108.0
C4—C5—C6111.33 (17)C4'—C5'—C6'111.02 (17)
C4—C5—H5A109.4C4'—C5'—H5'1109.4
C6—C5—H5A109.4C6'—C5'—H5'1109.4
C4—C5—H5B109.4C4'—C5'—H5'2109.4
C6—C5—H5B109.4C6'—C5'—H5'2109.4
H5A—C5—H5B108.0H5'1—C5'—H5'2108.0
C5—C6—C1111.96 (16)C1'—C6'—C5'111.56 (16)
C5—C6—H6A109.2C1'—C6'—H6'1109.3
C1—C6—H6A109.2C5'—C6'—H6'1109.3
C5—C6—H6B109.2C1'—C6'—H6'2109.3
C1—C6—H6B109.2C5'—C6'—H6'2109.3
H6A—C6—H6B107.9H6'1—C6'—H6'2108.0
C8—C7—C1179.5 (2)C8'—C7'—C1'177.8 (2)
C7—C8—H8177.6 (16)C7'—C8'—H8'176.3 (15)
C10—C9—C2176.1 (2)C10'—C9'—C2'176.7 (2)
C9—C10—H10178.7 (17)C9'—C10'—H10'174.6 (17)
C1—O1—H01105.7 (18)C1'—O1'—H01'107.8 (19)
C2—O2—H02105.5 (18)C2'—O2'—H02'105.4 (19)
O1—C1—C2—O2−68.27 (19)O1'—C1'—C2'—O2'67.18 (18)
C7—C1—C2—O253.3 (2)C7'—C1'—C2'—O2'−52.58 (19)
C6—C1—C2—O2175.02 (14)C6'—C1'—C2'—O2'−175.51 (15)
O1—C1—C2—C952.0 (2)O1'—C1'—C2'—C9'−51.7 (2)
C7—C1—C2—C9173.59 (15)C7'—C1'—C2'—C9'−171.47 (16)
C6—C1—C2—C9−64.7 (2)C6'—C1'—C2'—C9'65.6 (2)
O1—C1—C2—C3174.20 (15)O1'—C1'—C2'—C3'−172.81 (15)
C7—C1—C2—C3−64.18 (19)C7'—C1'—C2'—C3'67.4 (2)
C6—C1—C2—C357.49 (19)C6'—C1'—C2'—C3'−55.5 (2)
O2—C2—C3—C4−177.28 (15)O2'—C2'—C3'—C4'171.72 (16)
C9—C2—C3—C464.0 (2)C9'—C2'—C3'—C4'−65.7 (2)
C1—C2—C3—C4−57.8 (2)C1'—C2'—C3'—C4'54.9 (2)
C2—C3—C4—C556.2 (2)C2'—C3'—C4'—C5'−55.0 (2)
C3—C4—C5—C6−54.4 (2)C3'—C4'—C5'—C6'54.8 (2)
C4—C5—C6—C156.0 (2)O1'—C1'—C6'—C5'176.34 (15)
O1—C1—C6—C5−176.97 (16)C7'—C1'—C6'—C5'−65.1 (2)
C7—C1—C6—C563.4 (2)C2'—C1'—C6'—C5'57.2 (2)
C2—C1—C6—C5−57.2 (2)C4'—C5'—C6'—C1'−56.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H02···O1′0.83 (2)1.98 (2)2.787 (2)166 (3)
O2′—H02′···O2i0.83 (2)2.02 (2)2.837 (2)165 (3)
C10—H10···O2′ii0.95 (2)2.66 (2)3.495 (3)147 (2)
C8′—H8′···O1ii0.94 (2)2.53 (2)3.411 (3)156 (2)
C10′—H10′···O2iii0.94 (2)2.46 (2)3.272 (3)144 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) x, −y+3/2, z−1/2.
(IV) trans-1,4-diprop-2-ynylcyclohexane-1,4-diol hydrate top
Crystal data top
C12H18O3Z = 2
Mr = 210.26F(000) = 228
Triclinic, P1Dx = 1.222 Mg m−3
a = 6.6112 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2474 (19) ÅCell parameters from 56 reflections
c = 12.577 (3) Åθ = 10–11.5°
α = 93.384 (16)°µ = 0.09 mm−1
β = 102.410 (16)°T = 153 K
γ = 102.309 (16)°Prism, yellow
V = 571.5 (3) Å30.70 × 0.60 × 0.25 mm
Data collection top
Stoe STADI-4
diffractometer		Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.2°
Graphite monochromatorh = −7→7
ω/θ scansk = −8→8
2374 measured reflectionsl = −13→14
2022 independent reflections3 standard reflections every 60 min
1849 reflections with I > 2σ(I) intensity decay: none
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2046P]
where P = (Fo2 + 2Fc2)/3
2022 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.20 e Å−3
7 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C12H18O3γ = 102.309 (16)°
Mr = 210.26V = 571.5 (3) Å3
Triclinic, P1Z = 2
a = 6.6112 (18) ÅMo Kα radiation
b = 7.2474 (19) ŵ = 0.09 mm−1
c = 12.577 (3) ÅT = 153 K
α = 93.384 (16)°0.70 × 0.60 × 0.25 mm
β = 102.410 (16)°
Data collection top
Stoe STADI-4
diffractometer		Rint = 0.021
2374 measured reflections3 standard reflections every 60 min
2022 independent reflections intensity decay: none
1849 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0347 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.20 e Å−3
2022 reflectionsΔρmin = −0.20 e Å−3
160 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
O10.84693 (14)0.39717 (13)0.82084 (7)0.0223 (2)
H010.730 (3)0.414 (3)0.7798 (14)0.047 (5)*
C10.81482 (19)0.36043 (17)0.92784 (10)0.0196 (3)
C21.01113 (19)0.30015 (17)0.98931 (10)0.0216 (3)
H2A1.03310.19090.94570.026*
H2B0.98640.25781.05980.026*
C30.78829 (19)0.53954 (17)0.98833 (10)0.0212 (3)
H3A0.66810.58320.94400.025*
H3B0.75280.50871.05880.025*
C40.6122 (2)0.20182 (18)0.91501 (11)0.0243 (3)
H4A0.58990.17650.98860.029*
H4B0.48840.24660.87540.029*
C50.6205 (2)0.02421 (19)0.85603 (11)0.0249 (3)
C60.6284 (2)−0.1173 (2)0.80689 (12)0.0296 (3)
H60.633 (3)−0.230 (2)0.7677 (14)0.046 (5)*
O1'0.49797 (14)0.45806 (12)0.67637 (7)0.0216 (2)
H01'0.383 (3)0.477 (3)0.6934 (15)0.049 (5)*
C1'0.44261 (19)0.34810 (17)0.57046 (10)0.0193 (3)
C2'0.27312 (19)0.41941 (18)0.49225 (10)0.0206 (3)
H2'10.14680.41080.52370.025*
H2'20.22870.33660.42190.025*
C3'0.64711 (19)0.37550 (18)0.52919 (10)0.0206 (3)
H3'10.75880.33890.58420.025*
H3'20.62070.29060.46060.025*
C4'0.3643 (2)0.13701 (18)0.58442 (11)0.0238 (3)
H4'10.31500.06280.51120.029*
H4'20.48500.09050.62600.029*
C5'0.1907 (2)0.10345 (18)0.64148 (11)0.0265 (3)
C6'0.0553 (2)0.0849 (2)0.69061 (13)0.0354 (4)
H6'−0.049 (3)0.073 (3)0.7311 (15)0.053 (5)*
O30.17155 (17)0.58949 (16)0.73225 (10)0.0375 (3)
H030.070 (3)0.536 (3)0.7641 (17)0.071 (7)*
H040.179 (4)0.711 (2)0.739 (2)0.097 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0185 (5)0.0289 (5)0.0189 (5)0.0044 (4)0.0042 (4)0.0032 (4)
C10.0181 (6)0.0219 (6)0.0185 (6)0.0035 (5)0.0044 (5)0.0027 (5)
C20.0223 (6)0.0198 (6)0.0223 (6)0.0059 (5)0.0039 (5)0.0011 (5)
C30.0184 (6)0.0243 (7)0.0218 (6)0.0077 (5)0.0043 (5)0.0024 (5)
C40.0211 (7)0.0247 (7)0.0262 (7)0.0020 (5)0.0071 (5)0.0019 (5)
C50.0197 (6)0.0257 (7)0.0261 (7)−0.0007 (5)0.0037 (5)0.0063 (6)
C60.0292 (7)0.0230 (7)0.0338 (8)0.0009 (6)0.0066 (6)0.0027 (6)
O1'0.0201 (5)0.0253 (5)0.0193 (5)0.0062 (4)0.0044 (4)−0.0005 (4)
C1'0.0198 (6)0.0198 (6)0.0185 (6)0.0054 (5)0.0042 (5)0.0007 (5)
C2'0.0168 (6)0.0239 (6)0.0211 (6)0.0049 (5)0.0042 (5)0.0013 (5)
C3'0.0186 (6)0.0233 (6)0.0216 (6)0.0085 (5)0.0044 (5)0.0036 (5)
C4'0.0246 (7)0.0220 (7)0.0264 (7)0.0071 (5)0.0077 (5)0.0036 (5)
C5'0.0282 (7)0.0215 (7)0.0283 (7)0.0036 (5)0.0053 (6)0.0033 (5)
C6'0.0321 (8)0.0365 (8)0.0381 (8)0.0028 (6)0.0141 (7)0.0054 (7)
O30.0317 (6)0.0352 (6)0.0502 (7)0.0050 (5)0.0224 (5)0.0035 (5)
Geometric parameters (Å, º) top
O1—C11.4381 (15)O1'—H01'0.867 (15)
O1—H010.871 (15)C1'—C2'1.5242 (17)
C1—C21.5242 (17)C1'—C3'1.5284 (17)
C1—C31.5273 (17)C1'—C4'1.5403 (18)
C1—C41.5396 (17)C2'—C3'ii1.5279 (18)
C2—C3i1.5270 (18)C2'—H2'10.9900
C2—H2A0.9900C2'—H2'20.9900
C2—H2B0.9900C3'—H3'10.9900
C3—H3A0.9900C3'—H3'20.9900
C3—H3B0.9900C4'—C5'1.4654 (19)
C4—C51.4646 (19)C4'—H4'10.9900
C4—H4A0.9900C4'—H4'20.9900
C4—H4B0.9900C5'—C6'1.182 (2)
C5—C61.182 (2)C6'—H6'0.932 (16)
C6—H60.939 (16)O3—H030.884 (16)
O1'—C1'1.4437 (15)O3—H040.872 (17)
C1—O1—H01109.5 (12)O1'—C1'—C2'110.06 (10)
O1—C1—C2107.03 (10)O1'—C1'—C3'106.34 (10)
O1—C1—C3110.20 (10)C2'—C1'—C3'110.48 (10)
C2—C1—C3110.23 (10)O1'—C1'—C4'108.92 (10)
O1—C1—C4108.81 (10)C2'—C1'—C4'111.30 (10)
C2—C1—C4111.28 (10)C3'—C1'—C4'109.61 (10)
C3—C1—C4109.25 (10)C1'—C2'—C3'ii112.21 (10)
C1—C2—C3i112.44 (10)C1'—C2'—H2'1109.2
C1—C2—H2A109.1C3'ii—C2'—H2'1109.2
C3i—C2—H2A109.1C1'—C2'—H2'2109.2
C1—C2—H2B109.1C3'ii—C2'—H2'2109.2
C3i—C2—H2B109.1H2'1—C2'—H2'2107.9
H2A—C2—H2B107.8C2'ii—C3'—C1'112.22 (10)
C2i—C3—C1112.33 (10)C2'ii—C3'—H3'1109.2
C2i—C3—H3A109.1C1'—C3'—H3'1109.2
C1—C3—H3A109.1C2'ii—C3'—H3'2109.2
C2i—C3—H3B109.1C1'—C3'—H3'2109.2
C1—C3—H3B109.1H3'1—C3'—H3'2107.9
H3A—C3—H3B107.9C5'—C4'—C1'113.00 (11)
C5—C4—C1113.46 (11)C5'—C4'—H4'1109.0
C5—C4—H4A108.9C1'—C4'—H4'1109.0
C1—C4—H4A108.9C5'—C4'—H4'2109.0
C5—C4—H4B108.9C1'—C4'—H4'2109.0
C1—C4—H4B108.9H4'1—C4'—H4'2107.8
H4A—C4—H4B107.7C6'—C5'—C4'176.68 (15)
C6—C5—C4178.75 (14)C5'—C6'—H6'178.2 (12)
C5—C6—H6179.4 (11)H03—O3—H04107 (2)
C1'—O1'—H01'109.5 (12)
O1—C1—C2—C3i66.02 (13)O1'—C1'—C2'—C3'ii63.20 (13)
C3—C1—C2—C3i−53.83 (14)C3'—C1'—C2'—C3'ii−53.94 (14)
C4—C1—C2—C3i−175.21 (10)C4'—C1'—C2'—C3'ii−175.95 (10)
O1—C1—C3—C2i−64.15 (13)O1'—C1'—C3'—C2'ii−65.47 (13)
C2—C1—C3—C2i53.77 (15)C2'—C1'—C3'—C2'ii53.94 (15)
C4—C1—C3—C2i176.35 (10)C4'—C1'—C3'—C2'ii176.94 (10)
O1—C1—C4—C558.64 (14)O1'—C1'—C4'—C5'54.05 (14)
C2—C1—C4—C5−59.06 (14)C2'—C1'—C4'—C5'−67.47 (14)
C3—C1—C4—C5179.00 (11)C3'—C1'—C4'—C5'170.01 (11)
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O1′0.87 (2)1.88 (2)2.7470 (14)172 (2)
O1′—H01′···O30.87 (2)1.90 (2)2.7399 (15)164 (2)
O3—H03···O1iii0.88 (2)1.90 (2)2.7795 (15)174 (2)
C6—H6···O1′iv0.94 (2)2.37 (2)3.2516 (19)156 (2)
C6′—H6′···O1iii0.93 (2)2.83 (2)3.4004 (19)121 (1)
Symmetry codes: (iii) x−1, y, z; (iv) x, y−1, z.

Experimental details

(II)(IV)
Crystal data
Chemical formulaC10H12O2C12H18O3
Mr164.20210.26
Crystal system, space groupMonoclinic, P21/cTriclinic, P1
Temperature (K)153153
a, b, c (Å)10.563 (3), 23.839 (6), 7.025 (2)6.6112 (18), 7.2474 (19), 12.577 (3)
α, β, γ (°)90, 93.46 (2), 9093.384 (16), 102.410 (16), 102.309 (16)
V (Å3)1765.8 (8)571.5 (3)
Z82
Radiation typeMo KαMo Kα
µ (mm−1)0.090.09
Crystal size (mm)0.45 × 0.40 × 0.400.70 × 0.60 × 0.25
Data collection
DiffractometerStoe STADI-4Stoe STADI-4
Absorption correction––
No. of measured, independent and
observed [I > 2σ(I)] reflections		4400, 3131, 2380 2374, 2022, 1849
Rint0.0280.021
(sin θ/λ)max (Å−1)0.5960.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.103, 1.08 0.034, 0.084, 1.05
No. of reflections31312022
No. of parameters250160
No. of restraints127
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 Å−3)0.18, −0.180.20, −0.20

Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4 (Stoe & Cie, 1992), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) for (II) top
C1—O11.430 (2)C1'—O1'1.438 (2)
C2—O21.439 (2)C2'—O2'1.422 (2)
C7—C81.178 (3)C7'—C8'1.171 (3)
C9—C101.183 (3)C9'—C10'1.179 (3)
C8—C7—C1179.5 (2)C8'—C7'—C1'177.8 (2)
C10—C9—C2176.1 (2)C10'—C9'—C2'176.7 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O2—H02···O1'0.828 (19)1.976 (19)2.787 (2)166 (3)
O2'—H02'···O2i0.832 (19)2.02 (2)2.837 (2)165 (3)
C10—H10···O2'ii0.950 (18)2.66 (2)3.495 (3)147 (2)
C8'—H8'···O1ii0.940 (17)2.529 (19)3.411 (3)156 (2)
C10'—H10'···O2iii0.944 (18)2.46 (2)3.272 (3)144 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) x, −y+3/2, z−1/2.
Selected geometric parameters (Å, º) for (IV) top
O1—C11.4381 (15)O1'—C1'1.4437 (15)
C5—C61.182 (2)C5'—C6'1.182 (2)
C6—C5—C4178.75 (14)C6'—C5'—C4'176.68 (15)
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O1'0.871 (15)1.882 (15)2.7470 (14)172.2 (17)
O1'—H01'···O30.867 (15)1.895 (15)2.7399 (15)164.4 (17)
O3—H03···O1i0.884 (16)1.899 (16)2.7795 (15)174 (2)
C6—H6···O1'ii0.939 (16)2.370 (17)3.2516 (19)156.3 (15)
C6'—H6'···O1i0.932 (16)2.825 (18)3.4004 (19)121.0 (14)
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z.
 

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