Achiral (1R,2S,4r)-1,2,4-triphenylcyclopentane-1,2-diol and (1R,2S,4r)-4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol form one-dimensional chains via O—H⋯O hydrogen bonding in their crystals. The diols may serve as precatalyst activators for ring-opening polymerization of cyclic esters.
Keywords: cyclopentane-1,2-diol; crystal structure; hydrogen bonding; ring-opening polymerization; caprolactone
Abstract
Reductive cyclization of 1,3,5-triphenyl- and 3-(2-methoxyphenyl)-1,5-diphenylpentane-1,5-diones by zinc in acetic acid medium leads to the formation of 1,2,4-triphenylcyclopentane-1,2-diol [1,2,4-Ph3C5H5-1,2-(OH)2, C23H22O2, (I)] and 4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol [4-(2-MeOC6H4)-1,2-Ph2C5H5-1,2-(OH)2, C24H24O3, (II)]. Their single crystals have been obtained by crystallization from a THF/hexane solvent mixture. Diols (I) and (II) crystallize in orthorhombic (Pbca) and triclinic (P
) space groups, respectively, at 150 K. Their asymmetric units comprise one [in the case of (I)] and three [in the case of (II)] crystallographically independent molecules of the achiral (1R,2S,4r)-diol isomer. Each hydroxyl group is involved in one intramolecular and one intermolecular O—H⋯O hydrogen bond, forming one-dimensional chains. Compounds (I) and (II) have been used successfully as precatalyst activators for the ring-opening polymerization of ∊-caprolactone.
Chemical context
1,2,4-Triarylcyclopentane-1,2-diols are useful synthetic precursors for obtaining 1,2,4-triarylcyclopenta-1,3-dienes (Hirsch & Bailey, 1978 ▸; Yang et al., 2012 ▸; Zhang et al., 2013 ▸; Ye et al., 2016 ▸, 2017 ▸). The latter compounds are currently of interest because of their intrinsic luminescent properties due to aggregation-induced emission enhancement (Yang et al., 2012 ▸; Zhang, Ye et al., 2013 ▸; Ye et al., 2016 ▸, 2017 ▸). Certain 4-aryl-1,2-diphenylcyclopenta-1,3-dienes are promising candidates for the fabrication of OLED devices (Ye et al., 2017 ▸). However, most triarylcyclopentadienes are mainly used for the synthesis of the corresponding organometallic cyclopentadienyl complexes. Up to date, the number of known triphenylcyclopentadienyl complexes of d- (Davies et al., 2000 ▸; Deck et al., 2006 ▸; Thornberry et al., 2000 ▸, 2004 ▸; Wu et al., 2007 ▸; Xu et al., 2006 ▸, 2007 ▸; Zhang et al., 2000 ▸; Zhang et al., 2003 ▸) and f-block metals (Visseaux et al., 2008 ▸; Minyaev et al., 2016 ▸; Roitershtein et al., 2012 ▸, 2018 ▸) is rather limited, and they are still insufficiently studied. Various polyphenylcyclopentadienyl Tb complexes, including 1,2,4-triphenylcyclopentadienyl ones, display promising photophysical properties because of the presence of such a ligand, which serves as a π-type antenna for luminescence sensitization of lanthanides (Roitershtein et al., 2018 ▸). Organometallic derivatives of d- and f-block metals with various triphenylcyclopentadienyl ligands may also be used in the catalytic polymerization of olefins (Thornberry et al., 2004 ▸; Visseaux et al., 2008 ▸; Minyaev et al., 2016 ▸; Xu et al., 2006 ▸, 2007 ▸; Zhang et al., 2000 ▸; Zhang et al., 2003 ▸).
1,2-Diphenyl-4-arylcyclopentane-1,2-diols can be readily synthesized by the reductive cyclization of 1,5-diphenyl-3-arylpentane-1,5-diones with zinc in an acetic acid medium (Fig. 1 ▸; aryl = Ph, 2-MeOC6H4). The corresponding diones are formed by condensation of acetophenone with benzaldehyde/2-methoxybenzaldehyde under basic conditions (Hirsch & Bailey, 1978 ▸; Minyaev et al., 2015 ▸). The presence of only one isomer (see §2) has been detected by 1H NMR studies in the samples of all isolated crystalline diols from repeated syntheses. However, examination of the reaction mixtures has allowed us to suppose that another minor isomer of (I) may sometimes be present (up to 20%), but it does not crystallize under the conditions used here.
Figure 1.
Synthesis of 1,2,4-triphenylcyclopentane-1,2-diol (I) and 4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II).
It is known that complexes [Mg(BHT)(OR)(THF)n]2 (n = 0, 1; BHT = O-2,6-tBu2-4-MeC6H2 or the anion of butylated hydroxytoluene) are active in ring-opening polymerization (ROP) of cyclic esters (Nifant’ev et al., 2016 ▸, 2017 ▸), whereas Mg(BHT)2(THF)2 is catalytically inactive, but displays relatively high catalytic activity upon activation by a primary alcohol (see, for example, Chen et al., 2012 ▸). The ROP of ∊-caprolactone (∊-CL) to poly(∊-caprolactone) (PCL) can be carried out on the precatalyst Mg(BHT)2(THF)2 activated even by various bulky alcohols (Minyaev et al., 2018 ▸). We have tested the obtained diols (I) and (II) as activators of the Mg(BHT)2(THF)2 precatalyst for polymerization of ∊-CL (Fig. 2 ▸, Table 1 ▸). In all cases, the quantitative conversion of ∊-CL to PCL was observed by 1H NMR spectroscopy.
Figure 2.
Ring-opening polymerization of ∊-caprolactone using [Mg(BHT)2(THF)2] and either (I) or (II).
Table 1. Polymerization of ∊-CL.
Mn is the number-average molar mass; Đ is the polydispersity index defined as Đ=Mw/Mn, where Mw is the weight-average molar mass; Pn is the polymerization degree. Conditions: [∊-CL] = 2.5 M; THF; [∊-CL]/[diol]/[Mg(BHT)2] = 100:1:1 or 2; 300 K, 30 min.
| Entry | Diol | Equiv. of Mg(BHT)2 | Mn ×103a | Ða | Pna | Mn ×103b | Pnb |
|---|---|---|---|---|---|---|---|
| 1 | (I) | 1 | 11.4 | 1.42 | 97 | 12.0 | 102 |
| 2 | (I) | 2 | 9.0 | 1.84 | 77 | 7.6 | 65 |
| 3 | (II) | 1 | 12.4 | 1.39 | 106 | 12.6 | 107 |
| 4 | (II) | 2 | 8.9 | 1.85 | 76 | 7.2 | 62 |
Notes: (a) Found by size-exclusion chromatography (SEC) measurements. (b) Determined by 1H NMR studies. Mn and Pn were calculated based on the end-group analysis.
In the case of the ratio [diol]/[Mg(BHT)2] = 1:1 (entries 1 and 3, Table 1 ▸), the polymerization degree (the number of polymerized monomer units, Pn) found by 1H NMR spectroscopy and by size-exclusion chromatography (SEC) are very close to the calculated value (Pn calcd. = 100). However, when the ratio [diol]/[Mg(BHT)2] = 1:2, and two chains are growing at one diol, the Pn values (entries 2 and 4) are somewhat higher than expected (Pn calcd. = 50), which might be explained by a longer reaction time of the second [Mg(BHT)2(THF)2] molecule with the same initiator molecule with respect to the time of polymer-chain propagation. This is also supported by larger polydispersity index (Đ) values (compare entries 2 and 4 with entries 1 and 3), pointing to unequal growth of the two chains.
Therefore, catalytic tests have shown that systems based on [Mg(BHT)2(THF)2] and (I) or (II) are capable of catalysing ROP of ∊-CL, providing 100% monomer conversion. When using the diol/Mg(BHT)2 ratio equal to 1:1, the ROP can be carried out in a more controlled manner.
Structural commentary
Compounds (I) and (II) crystallize in the orthorhombic Pbca and triclinic P
space groups, respectively. The asymmetric units of (I) and (II) contain one and three diol molecules, respectively, exhibiting an achiral configuration (1R,2S,4r) with all three phenyl groups being on one side of the cyclopentane ring (Figs. 3 ▸ and 4 ▸). However, the envelope conformations of (I) and (II) differ, which might be caused by crystal-packing effects. Thus, atoms C1, C2, C3 and C5 in (I) lie nearly in one plane but atom C4 deviates by 0.6727 (19) Å from the plane (see Scheme and Fig. 3 ▸). All three crystallographically independent molecules in (II) (A, B and C; Fig. 4 ▸) have very similar envelope conformations (with the exception of the positions of the hydroxy H atoms), with atom C2 being out of the plane formed by atoms C1, C3, C4 and C5 by 0.644 (3), 0.666 (3) and 0.633 (3) Å in (II
A), (II
B) and (II
C), respectively (see Scheme and Fig. 4 ▸). A conformation which is very similar to those of molecules (II
A), (II
B) and (II
C) has been found earlier for (1R,2S)-1,2-diphenylcyclopentane-1,2-diol, having the Cambridge Structural Database (Version 5.40; Groom et al., 2016 ▸) refcode ZIWVEG (Choi et al., 1995 ▸). All C—C and C—O bond distances in (I) and (II) fall into regular ranges and can be found in the supporting information.
Figure 3.
The structure of (1R,2S,4r)-1,2,4-triphenylcyclopentane-1,2-diol, (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Only hydroxy H atoms are labelled for clarity. The intramolecular hydrogen bonding is not shown.
Figure 4.
The structure of the three crystallographically independent molecules (A, B, C) of (1R,2S,4r)-4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol, (II). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Only hydroxy H atoms are labelled for clarity. The intramolecular hydrogen bonding is not shown.
Diols (I) and (II) each form one intramolecular O—H⋯O hydrogen bond: O2—H2⋯O1 for (I), O2A—H2A⋯O1A for (II A), O1B—H1B⋯O2B for (II B) and O2C—H2C⋯O1C for (II C) (Figs. 5 ▸, 6 ▸). The corresponding O—H⋯O bond angles range from 117 (2)° in (II B) to 131.0 (19)° in (I) (Tables 2 ▸ and 3 ▸).
Figure 5.
The one-dimensional chains formed by hydrogen bonding between molecules of (1R,2S,4r)-1,2,4-triphenylcyclopentane-1,2-diol (I) parallel to the b axis. Displacement ellipsoids are drawn at the 50% probability level. Non-hydroxy H atoms are not shown.
Figure 6.
The one-dimensional chains of (1R,2S,4r)-4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol molecules (II) along the ab direction. Displacement ellipsoids are drawn at the 50% probability level. Non-hydroxy H atoms are not shown.
Table 2. Hydrogen-bond geometry (Å, °) for I .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯O2i | 0.87 (2) | 1.89 (2) | 2.7509 (13) | 173.2 (19) |
| O2—H2⋯O1 | 0.86 (2) | 1.80 (2) | 2.4510 (14) | 131.0 (19) |
Symmetry code: (i) 
.
Table 3. Hydrogen-bond geometry (Å, °) for (II) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1A—H1A⋯O2C ii | 0.85 (3) | 2.08 (3) | 2.8931 (19) | 160 (3) |
| O2A—H2A⋯O1A | 0.88 (3) | 2.04 (3) | 2.605 (2) | 121 (2) |
| O1B—H1B⋯O2B | 0.90 (3) | 2.05 (3) | 2.590 (2) | 117 (2) |
| O2B—H2B⋯O2A | 0.83 (2) | 1.98 (2) | 2.802 (2) | 170 (2) |
| O1C—H1C⋯O1B | 0.88 (3) | 1.96 (3) | 2.833 (2) | 171 (2) |
| O2C—H2C⋯O1C | 0.85 (3) | 2.00 (3) | 2.587 (2) | 125 (2) |
Symmetry code: (ii) 
.
Supramolecular features
Regardless of some structural differences, diols (I) and (II) form similar 1D chains in their crystals via intermolecular O—H⋯O hydrogen bonding [O1—H1⋯O2i for (I), symmetry code: (i) −x + 
, y − , z; and O2B—H2B⋯O2A, O1C—H1C⋯O1B, O1A—H1A⋯O2C
ii for (II), symmetry code: (ii) x − 1, y − 1, z]. The intermolecular O—H⋯O bond angles lie in the expected range of 160 (3) to 173.2 (19)°. The chains are oriented along the b-axis direction in (I) and approximately along the ab diagonal in (II). It might be also mentioned that for both the inter- and intramolecular hydrogen bonds, the O⋯O and consequently O—H⋯O distances are slightly elongated in (II) compared to (I), likely as a result of crystal-packing effects.
Synthesis and crystallization
General remarks
The starting compounds 1,3,5-triphenylpentane-1,5-dione and 3-(2-methoxyphenyl)-1,5-diphenylpentane-1,5-dione were obtained in high yields by the previously described procedure (Hirsch & Bailey, 1978 ▸) with certain minor modifications (Minyaev et al., 2015 ▸) to decrease formation of side products. They were recrystallized from hot ethanol or isopropanol followed by vacuum drying. The complex Mg(BHT)2(THF)2 was prepared as described earlier (Nifant’ev et al., 2017 ▸). All polymerization tests and the synthesis of Mg(BHT)2(THF)2 were performed under a purified argon atmosphere in a dry box in absolute solvent media. Tetrahydrofuran was pre-dried over NaOH and distilled from potassium/benzophenone ketyl. Hexane was distilled from an Na/K alloy. Toluene was distilled from sodium/benzophenone ketyl. ∊-Caprolactone (∊-CL) was distilled from CaH2 under reduced pressure of argon. CDCl3 (Cambridge Isotope Laboratories, Inc., D 99.8%) was used as purchased. The NMR spectra were recorded on Bruker AV400 and AV600 spectrometers at 300 K; chemical shifts are reported in ppm relative to the solvent residual peak. The SEC analysis of polymer samples was performed at 323 K using an Agilent PL-GPC 220 gel permeation chromatograph equipped with a PLgel column, with DMF as eluent (1 ml min−1) and poly(ethylene oxide) standards.
Synthesis and crystallization of (I)
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol, (I), was prepared as described previously (Hirsch & Bailey, 1978 ▸) in a yield of 78%, m.p. = 415–417K. 1H NMR (400 MHz, CDCl3): δ = 2.61 (2H, dd, –CH2–, 2 J HH = 13.9 Hz, 3 J HH = 8.8 Hz), 2.84 (2H, dd, –CH2–, 2 J HH = 13.9 Hz, 3 J HH = 10.1 Hz), 3.58 (2H, s, >CPh—OH), 4.11 (1H, quintet, >CPhH), 6.97–7.12 (10H, m), 7.15–7.36 (2H, m), 7.43 (3H, d, 3 J HH = 4.0 Hz).
A small portion of (I) was dissolved in a warm mixture of THF/hexane (1:10 v/v) to provide a saturated solution. Single crystals formed in two weeks.
Synthesis and crystallization of (II)
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol, (II), was prepared analogously to (I) but with some minor modifications. Zinc powder (20.00 g, 306 mmol) was added by small portions over 5 h to a vigorously stirred solution of 1,5-diphenyl-3-(2-methoxyphenyl)pentane-1,5-dione (27.43 g, 76.5 mmol) in 900 ml of glacial acetic acid at 363 K. The formed hot mixture was filtered. The resulting solution was cooled to room temperature and poured into 5000 ml of water. The formed yellowish precipitate was collected, washed with water (2 × 100 ml) and dried under vacuum. The solid was recrystallized from a hot mixture of petroleum ether (boiling temperature range of 343–373 K) and toluene (400 ml, 3:1 v/v). The white microcrystals were dried under dynamic vacuum. The yield was 17.42 g (48.3 mmol, 63.2%), (m.p. = 384–387 K. 1H NMR (600 MHz, CDCl3): δ = 2.56 (2H, dd, –CH2–, 2 J HH = 14.3 Hz, 3 J HH = 8.4 Hz), 2.81 (2H, dd, –CH2–, 2 J HH = 14.3 Hz, 3 J HH = 10.3 Hz), 3.46 (2H, s, >CPh—OH), 3.90 (3H, s, –OCH3), 4.27 [1H, quintet, –C(C6H4OMe)H], 6.96 (1H, d, 3 J HH = 8.1 Hz), 7.02–7.07 (7H, m), 7.09–7.13 (4H, m), 7.31 (1H, t), 7.45 (1H, d, 3 J HH = 7.3 Hz). 13C{1H} NMR (150.9 MHz, CDCl3): δ = 34.07, 44.21, 55.40, 85.58, 110.67, 120.52, 126.34, 126.47, 126.82, 127.34, 127.48, 132.17, 143.51, 158.26.
Single crystals of (II), suitable for X-ray diffraction analysis, were grown from a THF/hexane mixture (1:10 v/v) over two weeks.
Polymerization procedure
In a typical polymerization experiment, a solution of 0.1 mmol of a diol [33 mg of (I) or 36 mg of (II)] in 1 ml of THF was added to a stirred solution of Mg(BHT)2(THF)2 (0.1 mmol, 61 mg or 0.2 mmol, 121 mg) in 1 ml of THF. The resulting solution was stirred for 20 min. A solution of ∊-CL (1.14 g, 10 mmol) in 1 ml of THF was then added at once to the formed catalyst solution. The solution was stirred for 30 min and then a sample was taken to determine conversion of the monomer by 1H NMR spectroscopy. A 100% conversion was established in all cases based on the absence of a resonance signal at 4.22 ppm (∊-CL) and the presence of a signal at 4.05 ppm (PCL), both corresponding to the –CH2O(CO)– fragment. The remaining viscous solution was poured into methanol (50 ml) containing a drop of acetic acid. The resulting precipitate was separated by centrifugation, washed with methanol (3 × 25 ml) and hexane (2 × 10 ml) and dried under vacuum. Polymer samples were further studied by SEC and 1H NMR analysis. The degree of polymerization was determined by integration of a PCL terminal group signal at 3.63 ppm (–CH2—CH2—OH).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. The positions of all hydrogen atoms in (I) and the hydroxy H atoms in (II) were found from the difference maps. These H atoms were refined independently with individual isotropic displacement parameters. The other H atoms in (II) were positioned geometrically (C—H = 0.95 Å for aromatic, 0.98 Å for methyl, 0.99 Å for methylene and 1.00 Å for methine H atoms) and refined as riding atoms with relative isotropic displacement parameters U
iso(H)= 1.5U
eq(C) for methyl H atoms and 1.2U
eq(C) otherwise. A rotating group model was applied for methyl groups. For (II), reflections 10 and 221 were affected by the beam stop and were omitted from the refinement. The extinction correction in SHELXL was used for (II) (Sheldrick, 2015 ▸).
Table 4. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C23H22O2 | C24H24O3 |
| M r | 330.40 | 360.43 |
| Crystal system, space group | Orthorhombic, P b c a | Triclinic, P
|
| Temperature (K) | 150 | 150 |
| a, b, c (Å) | 16.9915 (6), 9.3183 (3), 22.0129 (7) | 11.4136 (6), 14.0145 (7), 19.0339 (10) |
| α, β, γ (°) | 90, 90, 90 | 92.3394 (18), 101.5461 (17), 105.0129 (19) |
| V (Å3) | 3485.3 (2) | 2867.3 (3) |
| Z | 8 | 6 |
| Radiation type | Mo Kα | Mo Kα |
| μ (mm−1) | 0.08 | 0.08 |
| Crystal size (mm) | 0.40 × 0.35 × 0.20 | 0.50 × 0.20 × 0.10 |
| Data collection | ||
| Diffractometer | Bruker SMART APEXII | Bruker SMART APEXII |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.869, 0.928 | 0.856, 0.928 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 39896, 4625, 4025 | 31335, 11202, 8043 |
| R int | 0.041 | 0.039 |
| (sin θ/λ)max (Å−1) | 0.682 | 0.617 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.055, 0.136, 1.11 | 0.051, 0.136, 1.04 |
| No. of reflections | 4625 | 11202 |
| No. of parameters | 314 | 758 |
| H-atom treatment | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.40, −0.23 | 0.36, −0.24 |
Supplementary Material
Crystal structure: contains datablock(s) I, II, New_Global_Publ_Block. DOI: 10.1107/S2056989019008673/fy2139sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019008673/fy2139Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989019008673/fy2139IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989019008673/fy2139Isup4.cml
Supporting information file. DOI: 10.1107/S2056989019008673/fy2139IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The equipment from the collective exploitation center ‘New petrochemical processes, polymer composites and adhesives’ of TIPS RAS was used. The X-ray diffraction studies were performed at the Centre of Shared Equipment of IGIC RAS.
supplementary crystallographic information
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Crystal data
| C23H22O2 | Dx = 1.259 Mg m−3 |
| Mr = 330.40 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pbca | Cell parameters from 9996 reflections |
| a = 16.9915 (6) Å | θ = 3.0–30.4° |
| b = 9.3183 (3) Å | µ = 0.08 mm−1 |
| c = 22.0129 (7) Å | T = 150 K |
| V = 3485.3 (2) Å3 | Prism, colourless |
| Z = 8 | 0.40 × 0.35 × 0.20 mm |
| F(000) = 1408 |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Data collection
| Bruker SMART APEXII diffractometer | 4625 independent reflections |
| Radiation source: fine-focus sealed tube | 4025 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.041 |
| ω scans | θmax = 29.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −22→23 |
| Tmin = 0.869, Tmax = 0.928 | k = −12→12 |
| 39896 measured reflections | l = −30→29 |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Refinement
| 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)] = 0.055 | Hydrogen site location: difference Fourier map |
| wR(F2) = 0.136 | All H-atom parameters refined |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.0649P)2 + 1.4502P] where P = (Fo2 + 2Fc2)/3 |
| 4625 reflections | (Δ/σ)max < 0.001 |
| 314 parameters | Δρmax = 0.40 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.24602 (5) | 0.55215 (10) | 0.18770 (4) | 0.0209 (2) | |
| H1 | 0.2241 (12) | 0.469 (2) | 0.1826 (9) | 0.037 (5)* | |
| O2 | 0.31200 (6) | 0.78090 (10) | 0.16702 (5) | 0.0211 (2) | |
| H2 | 0.2699 (13) | 0.731 (2) | 0.1629 (9) | 0.040 (5)* | |
| C1 | 0.32785 (7) | 0.53090 (13) | 0.20268 (6) | 0.0154 (2) | |
| C2 | 0.36409 (7) | 0.69000 (13) | 0.20090 (6) | 0.0156 (2) | |
| C3 | 0.36604 (8) | 0.73633 (14) | 0.26866 (6) | 0.0197 (3) | |
| H3A | 0.4214 (10) | 0.7274 (18) | 0.2843 (8) | 0.026 (4)* | |
| H3B | 0.3500 (10) | 0.8380 (19) | 0.2727 (7) | 0.023 (4)* | |
| C4 | 0.31240 (7) | 0.63121 (14) | 0.30256 (6) | 0.0182 (3) | |
| H4 | 0.2562 (10) | 0.6555 (17) | 0.2932 (7) | 0.019 (4)* | |
| C5 | 0.33277 (8) | 0.49036 (13) | 0.26981 (6) | 0.0185 (3) | |
| H5A | 0.2978 (10) | 0.4132 (19) | 0.2798 (8) | 0.026 (4)* | |
| H5B | 0.3860 (9) | 0.4584 (17) | 0.2823 (7) | 0.018 (4)* | |
| C6 | 0.36313 (7) | 0.42551 (13) | 0.15783 (6) | 0.0178 (3) | |
| C7 | 0.39703 (8) | 0.29720 (14) | 0.17635 (7) | 0.0233 (3) | |
| H7 | 0.3998 (10) | 0.2754 (19) | 0.2195 (9) | 0.030 (5)* | |
| C8 | 0.42672 (9) | 0.20104 (17) | 0.13381 (8) | 0.0327 (4) | |
| H8 | 0.4512 (13) | 0.112 (2) | 0.1483 (9) | 0.045 (6)* | |
| C9 | 0.42272 (10) | 0.23193 (19) | 0.07249 (8) | 0.0371 (4) | |
| H9 | 0.4433 (12) | 0.164 (2) | 0.0424 (10) | 0.049 (6)* | |
| C10 | 0.38891 (11) | 0.3595 (2) | 0.05359 (7) | 0.0386 (4) | |
| H10 | 0.3878 (13) | 0.384 (2) | 0.0106 (10) | 0.050 (6)* | |
| C11 | 0.35920 (9) | 0.45546 (17) | 0.09590 (7) | 0.0285 (3) | |
| H11 | 0.3358 (11) | 0.546 (2) | 0.0819 (8) | 0.034 (5)* | |
| C12 | 0.44573 (7) | 0.70012 (13) | 0.17266 (6) | 0.0163 (2) | |
| C13 | 0.50697 (8) | 0.61131 (14) | 0.19234 (6) | 0.0209 (3) | |
| H13 | 0.4978 (11) | 0.541 (2) | 0.2244 (8) | 0.032 (5)* | |
| C14 | 0.58129 (8) | 0.62098 (15) | 0.16632 (7) | 0.0249 (3) | |
| H14 | 0.6240 (11) | 0.556 (2) | 0.1803 (8) | 0.033 (5)* | |
| C15 | 0.59666 (8) | 0.72139 (16) | 0.12135 (7) | 0.0259 (3) | |
| H15 | 0.6492 (11) | 0.730 (2) | 0.1042 (8) | 0.030 (5)* | |
| C16 | 0.53730 (9) | 0.81218 (16) | 0.10270 (6) | 0.0266 (3) | |
| H16 | 0.5474 (11) | 0.887 (2) | 0.0723 (9) | 0.037 (5)* | |
| C17 | 0.46217 (8) | 0.80077 (15) | 0.12783 (6) | 0.0219 (3) | |
| H17 | 0.4216 (11) | 0.860 (2) | 0.1137 (8) | 0.034 (5)* | |
| C18 | 0.32029 (7) | 0.62406 (15) | 0.37101 (6) | 0.0209 (3) | |
| C19 | 0.36629 (9) | 0.71880 (17) | 0.40436 (7) | 0.0283 (3) | |
| H19 | 0.3956 (11) | 0.791 (2) | 0.3842 (8) | 0.028 (4)* | |
| C20 | 0.36941 (10) | 0.7090 (2) | 0.46775 (8) | 0.0374 (4) | |
| H20 | 0.4009 (13) | 0.777 (2) | 0.4892 (10) | 0.047 (6)* | |
| C21 | 0.32644 (10) | 0.6053 (2) | 0.49798 (7) | 0.0384 (4) | |
| H21 | 0.3280 (12) | 0.602 (2) | 0.5425 (10) | 0.044 (5)* | |
| C22 | 0.28124 (9) | 0.5092 (2) | 0.46516 (7) | 0.0333 (4) | |
| H22 | 0.2512 (12) | 0.437 (2) | 0.4862 (9) | 0.040 (5)* | |
| C23 | 0.27780 (8) | 0.51904 (17) | 0.40237 (6) | 0.0255 (3) | |
| H23 | 0.2437 (11) | 0.4513 (19) | 0.3798 (8) | 0.029 (4)* |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0128 (4) | 0.0168 (4) | 0.0331 (5) | −0.0001 (3) | −0.0051 (4) | −0.0042 (4) |
| O2 | 0.0159 (4) | 0.0154 (4) | 0.0319 (5) | 0.0033 (3) | −0.0044 (4) | 0.0023 (4) |
| C1 | 0.0123 (5) | 0.0119 (5) | 0.0220 (6) | −0.0001 (4) | −0.0030 (4) | −0.0014 (4) |
| C2 | 0.0147 (5) | 0.0121 (5) | 0.0202 (6) | 0.0009 (4) | −0.0023 (4) | −0.0011 (4) |
| C3 | 0.0210 (6) | 0.0169 (6) | 0.0211 (6) | −0.0026 (5) | −0.0004 (5) | −0.0044 (5) |
| C4 | 0.0155 (5) | 0.0187 (6) | 0.0205 (6) | 0.0014 (4) | 0.0001 (5) | −0.0021 (5) |
| C5 | 0.0196 (6) | 0.0151 (5) | 0.0207 (6) | −0.0005 (5) | −0.0005 (5) | −0.0006 (5) |
| C6 | 0.0139 (5) | 0.0164 (6) | 0.0232 (6) | −0.0017 (4) | −0.0018 (4) | −0.0052 (5) |
| C7 | 0.0215 (6) | 0.0177 (6) | 0.0307 (7) | 0.0018 (5) | −0.0010 (5) | −0.0026 (5) |
| C8 | 0.0287 (7) | 0.0225 (7) | 0.0470 (9) | 0.0059 (6) | −0.0001 (7) | −0.0099 (6) |
| C9 | 0.0317 (8) | 0.0394 (9) | 0.0402 (9) | 0.0042 (7) | 0.0004 (7) | −0.0231 (7) |
| C10 | 0.0436 (9) | 0.0476 (10) | 0.0245 (7) | 0.0074 (8) | −0.0038 (7) | −0.0133 (7) |
| C11 | 0.0334 (8) | 0.0286 (7) | 0.0236 (7) | 0.0053 (6) | −0.0064 (6) | −0.0052 (6) |
| C12 | 0.0158 (5) | 0.0136 (5) | 0.0194 (5) | −0.0012 (4) | −0.0023 (4) | −0.0032 (4) |
| C13 | 0.0174 (6) | 0.0165 (6) | 0.0288 (7) | −0.0004 (5) | −0.0020 (5) | 0.0025 (5) |
| C14 | 0.0167 (6) | 0.0195 (6) | 0.0385 (8) | 0.0017 (5) | −0.0018 (5) | −0.0015 (6) |
| C15 | 0.0192 (6) | 0.0267 (7) | 0.0317 (7) | −0.0038 (5) | 0.0050 (5) | −0.0056 (6) |
| C16 | 0.0283 (7) | 0.0292 (7) | 0.0224 (6) | −0.0044 (6) | 0.0028 (5) | 0.0032 (6) |
| C17 | 0.0210 (6) | 0.0216 (6) | 0.0230 (6) | 0.0005 (5) | −0.0024 (5) | 0.0019 (5) |
| C18 | 0.0166 (6) | 0.0252 (7) | 0.0209 (6) | 0.0059 (5) | 0.0013 (5) | −0.0032 (5) |
| C19 | 0.0264 (7) | 0.0326 (8) | 0.0260 (7) | −0.0002 (6) | −0.0008 (6) | −0.0065 (6) |
| C20 | 0.0332 (8) | 0.0514 (10) | 0.0275 (8) | 0.0014 (8) | −0.0042 (6) | −0.0121 (7) |
| C21 | 0.0321 (8) | 0.0627 (12) | 0.0202 (7) | 0.0069 (8) | −0.0008 (6) | −0.0020 (7) |
| C22 | 0.0274 (7) | 0.0458 (9) | 0.0267 (7) | 0.0042 (7) | 0.0053 (6) | 0.0054 (7) |
| C23 | 0.0204 (6) | 0.0311 (7) | 0.0250 (7) | 0.0025 (6) | 0.0020 (5) | −0.0006 (6) |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Geometric parameters (Å, º)
| O1—C1 | 1.4426 (14) | C10—C11 | 1.387 (2) |
| O1—H1 | 0.87 (2) | C10—H10 | 0.97 (2) |
| O2—C2 | 1.4343 (15) | C11—H11 | 0.98 (2) |
| O2—H2 | 0.86 (2) | C12—C17 | 1.3898 (18) |
| C1—C6 | 1.5162 (17) | C12—C13 | 1.3985 (17) |
| C1—C5 | 1.5274 (18) | C13—C14 | 1.3895 (19) |
| C1—C2 | 1.6058 (17) | C13—H13 | 0.978 (19) |
| C2—C12 | 1.5230 (17) | C14—C15 | 1.387 (2) |
| C2—C3 | 1.5531 (18) | C14—H14 | 0.995 (19) |
| C3—C4 | 1.5319 (18) | C15—C16 | 1.379 (2) |
| C3—H3A | 1.005 (17) | C15—H15 | 0.972 (19) |
| C3—H3B | 0.990 (17) | C16—C17 | 1.395 (2) |
| C4—C18 | 1.5142 (18) | C16—H16 | 0.980 (19) |
| C4—C5 | 1.5369 (17) | C17—H17 | 0.94 (2) |
| C4—H4 | 1.002 (16) | C18—C19 | 1.389 (2) |
| C5—H5A | 0.959 (17) | C18—C23 | 1.398 (2) |
| C5—H5B | 0.990 (16) | C19—C20 | 1.399 (2) |
| C6—C7 | 1.3883 (18) | C19—H19 | 0.950 (19) |
| C6—C11 | 1.3930 (19) | C20—C21 | 1.382 (3) |
| C7—C8 | 1.391 (2) | C20—H20 | 0.96 (2) |
| C7—H7 | 0.973 (19) | C21—C22 | 1.383 (3) |
| C8—C9 | 1.382 (3) | C21—H21 | 0.98 (2) |
| C8—H8 | 0.98 (2) | C22—C23 | 1.386 (2) |
| C9—C10 | 1.384 (3) | C22—H22 | 0.97 (2) |
| C9—H9 | 0.98 (2) | C23—H23 | 0.989 (18) |
| C1—O1—H1 | 108.6 (13) | C10—C9—H9 | 120.1 (13) |
| C2—O2—H2 | 104.6 (14) | C9—C10—C11 | 120.21 (16) |
| O1—C1—C6 | 108.72 (10) | C9—C10—H10 | 120.1 (13) |
| O1—C1—C5 | 107.93 (10) | C11—C10—H10 | 119.6 (13) |
| C6—C1—C5 | 116.62 (10) | C10—C11—C6 | 120.70 (15) |
| O1—C1—C2 | 103.73 (9) | C10—C11—H11 | 119.3 (11) |
| C6—C1—C2 | 115.50 (10) | C6—C11—H11 | 120.0 (11) |
| C5—C1—C2 | 103.36 (9) | C17—C12—C13 | 118.02 (12) |
| O2—C2—C12 | 108.25 (10) | C17—C12—C2 | 120.98 (11) |
| O2—C2—C3 | 110.39 (10) | C13—C12—C2 | 120.97 (11) |
| C12—C2—C3 | 110.82 (10) | C14—C13—C12 | 120.68 (13) |
| O2—C2—C1 | 108.74 (9) | C14—C13—H13 | 119.1 (11) |
| C12—C2—C1 | 114.61 (10) | C12—C13—H13 | 120.2 (11) |
| C3—C2—C1 | 103.96 (10) | C15—C14—C13 | 120.60 (13) |
| C4—C3—C2 | 106.10 (10) | C15—C14—H14 | 119.7 (11) |
| C4—C3—H3A | 109.7 (10) | C13—C14—H14 | 119.7 (11) |
| C2—C3—H3A | 109.0 (10) | C16—C15—C14 | 119.25 (13) |
| C4—C3—H3B | 113.8 (10) | C16—C15—H15 | 120.4 (11) |
| C2—C3—H3B | 110.3 (10) | C14—C15—H15 | 120.3 (11) |
| H3A—C3—H3B | 107.9 (14) | C15—C16—C17 | 120.29 (13) |
| C18—C4—C3 | 117.40 (11) | C15—C16—H16 | 120.7 (11) |
| C18—C4—C5 | 114.16 (11) | C17—C16—H16 | 119.0 (11) |
| C3—C4—C5 | 100.58 (10) | C12—C17—C16 | 121.12 (13) |
| C18—C4—H4 | 107.3 (9) | C12—C17—H17 | 119.1 (12) |
| C3—C4—H4 | 108.8 (9) | C16—C17—H17 | 119.7 (12) |
| C5—C4—H4 | 108.2 (9) | C19—C18—C23 | 118.32 (13) |
| C1—C5—C4 | 103.31 (10) | C19—C18—C4 | 123.22 (13) |
| C1—C5—H5A | 111.9 (10) | C23—C18—C4 | 118.45 (12) |
| C4—C5—H5A | 113.2 (10) | C18—C19—C20 | 120.45 (15) |
| C1—C5—H5B | 113.1 (9) | C18—C19—H19 | 120.0 (11) |
| C4—C5—H5B | 109.4 (9) | C20—C19—H19 | 119.5 (11) |
| H5A—C5—H5B | 106.1 (14) | C21—C20—C19 | 120.40 (16) |
| C7—C6—C11 | 118.68 (12) | C21—C20—H20 | 121.6 (13) |
| C7—C6—C1 | 122.04 (12) | C19—C20—H20 | 118.0 (13) |
| C11—C6—C1 | 119.24 (12) | C20—C21—C22 | 119.62 (15) |
| C6—C7—C8 | 120.50 (14) | C20—C21—H21 | 119.1 (12) |
| C6—C7—H7 | 119.1 (11) | C22—C21—H21 | 121.3 (12) |
| C8—C7—H7 | 120.4 (11) | C21—C22—C23 | 120.09 (16) |
| C9—C8—C7 | 120.38 (15) | C21—C22—H22 | 119.7 (12) |
| C9—C8—H8 | 120.9 (12) | C23—C22—H22 | 120.2 (12) |
| C7—C8—H8 | 118.7 (12) | C22—C23—C18 | 121.12 (14) |
| C8—C9—C10 | 119.54 (14) | C22—C23—H23 | 118.8 (10) |
| C8—C9—H9 | 120.4 (13) | C18—C23—H23 | 120.1 (10) |
| O1—C1—C2—O2 | −18.78 (12) | C9—C10—C11—C6 | 0.2 (3) |
| C6—C1—C2—O2 | 100.08 (12) | C7—C6—C11—C10 | −0.3 (2) |
| C5—C1—C2—O2 | −131.34 (10) | C1—C6—C11—C10 | −178.18 (14) |
| O1—C1—C2—C12 | −140.05 (10) | O2—C2—C12—C17 | 8.66 (16) |
| C6—C1—C2—C12 | −21.20 (15) | C3—C2—C12—C17 | −112.53 (13) |
| C5—C1—C2—C12 | 107.38 (11) | C1—C2—C12—C17 | 130.20 (12) |
| O1—C1—C2—C3 | 98.83 (11) | O2—C2—C12—C13 | −173.27 (11) |
| C6—C1—C2—C3 | −142.31 (11) | C3—C2—C12—C13 | 65.54 (15) |
| C5—C1—C2—C3 | −13.74 (12) | C1—C2—C12—C13 | −51.72 (16) |
| O2—C2—C3—C4 | 100.69 (12) | C17—C12—C13—C14 | −1.9 (2) |
| C12—C2—C3—C4 | −139.38 (10) | C2—C12—C13—C14 | 179.92 (12) |
| C1—C2—C3—C4 | −15.77 (12) | C12—C13—C14—C15 | 1.6 (2) |
| C2—C3—C4—C18 | 163.45 (10) | C13—C14—C15—C16 | 0.1 (2) |
| C2—C3—C4—C5 | 39.00 (12) | C14—C15—C16—C17 | −1.5 (2) |
| O1—C1—C5—C4 | −71.24 (12) | C13—C12—C17—C16 | 0.62 (19) |
| C6—C1—C5—C4 | 166.10 (10) | C2—C12—C17—C16 | 178.74 (12) |
| C2—C1—C5—C4 | 38.23 (11) | C15—C16—C17—C12 | 1.1 (2) |
| C18—C4—C5—C1 | −174.72 (10) | C3—C4—C18—C19 | 7.85 (19) |
| C3—C4—C5—C1 | −48.08 (12) | C5—C4—C18—C19 | 125.18 (14) |
| O1—C1—C6—C7 | −121.11 (13) | C3—C4—C18—C23 | −173.66 (12) |
| C5—C1—C6—C7 | 1.13 (17) | C5—C4—C18—C23 | −56.33 (16) |
| C2—C1—C6—C7 | 122.83 (13) | C23—C18—C19—C20 | −0.3 (2) |
| O1—C1—C6—C11 | 56.65 (15) | C4—C18—C19—C20 | 178.23 (14) |
| C5—C1—C6—C11 | 178.89 (12) | C18—C19—C20—C21 | −0.3 (3) |
| C2—C1—C6—C11 | −59.41 (16) | C19—C20—C21—C22 | 1.1 (3) |
| C11—C6—C7—C8 | 0.3 (2) | C20—C21—C22—C23 | −1.4 (3) |
| C1—C6—C7—C8 | 178.06 (13) | C21—C22—C23—C18 | 0.8 (2) |
| C6—C7—C8—C9 | −0.1 (2) | C19—C18—C23—C22 | 0.0 (2) |
| C7—C8—C9—C10 | 0.0 (3) | C4—C18—C23—C22 | −178.55 (13) |
| C8—C9—C10—C11 | −0.1 (3) |
(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol (I) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.87 (2) | 1.89 (2) | 2.7509 (13) | 173.2 (19) |
| O2—H2···O1 | 0.86 (2) | 1.80 (2) | 2.4510 (14) | 131.0 (19) |
Symmetry code: (i) −x+1/2, y−1/2, z.
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Crystal data
| C24H24O3 | Z = 6 |
| Mr = 360.43 | F(000) = 1152 |
| Triclinic, P1 | Dx = 1.252 Mg m−3 |
| a = 11.4136 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 14.0145 (7) Å | Cell parameters from 8113 reflections |
| c = 19.0339 (10) Å | θ = 2.4–29.8° |
| α = 92.3394 (18)° | µ = 0.08 mm−1 |
| β = 101.5461 (17)° | T = 150 K |
| γ = 105.0129 (19)° | Prism, colourless |
| V = 2867.3 (3) Å3 | 0.50 × 0.20 × 0.10 mm |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Data collection
| Bruker SMART APEXII diffractometer | 11202 independent reflections |
| Radiation source: fine-focus sealed tube | 8043 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.039 |
| ω scans | θmax = 26.0°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −14→14 |
| Tmin = 0.856, Tmax = 0.928 | k = −16→17 |
| 31335 measured reflections | l = −23→22 |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.7914P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 11202 reflections | Δρmax = 0.36 e Å−3 |
| 758 parameters | Δρmin = −0.24 e Å−3 |
| 0 restraints | Extinction correction: SHELXL2017 (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0066 (10) |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1A | 0.14728 (13) | 0.13460 (10) | 0.67974 (7) | 0.0287 (3) | |
| H1A | 0.102 (3) | 0.079 (2) | 0.6584 (15) | 0.072 (9)* | |
| O2A | 0.35980 (13) | 0.26985 (10) | 0.71380 (7) | 0.0295 (3) | |
| H2A | 0.301 (2) | 0.2451 (19) | 0.6748 (14) | 0.056 (8)* | |
| C1A | 0.22327 (18) | 0.12411 (13) | 0.74694 (10) | 0.0256 (4) | |
| C2A | 0.31467 (17) | 0.22962 (13) | 0.77471 (10) | 0.0238 (4) | |
| C3A | 0.42356 (18) | 0.20437 (14) | 0.82332 (10) | 0.0270 (4) | |
| H3AA | 0.402647 | 0.184037 | 0.869502 | 0.032* | |
| H3AB | 0.498165 | 0.262023 | 0.833524 | 0.032* | |
| C4A | 0.44566 (19) | 0.11847 (15) | 0.78056 (11) | 0.0326 (5) | |
| H4A | 0.495937 | 0.147876 | 0.745420 | 0.039* | |
| C5A | 0.31299 (19) | 0.06137 (15) | 0.73604 (12) | 0.0355 (5) | |
| H5AA | 0.314106 | 0.052394 | 0.684338 | 0.043* | |
| H5AB | 0.285661 | −0.004918 | 0.753057 | 0.043* | |
| C6A | 0.14252 (18) | 0.08553 (13) | 0.79971 (10) | 0.0278 (4) | |
| C7A | 0.1801 (2) | 0.03115 (15) | 0.85577 (12) | 0.0417 (6) | |
| H7A | 0.258336 | 0.017061 | 0.861285 | 0.050* | |
| C8A | 0.1053 (3) | −0.00218 (19) | 0.90302 (14) | 0.0575 (7) | |
| H8A | 0.132981 | −0.038195 | 0.941167 | 0.069* | |
| C9A | −0.0091 (3) | 0.01592 (19) | 0.89579 (14) | 0.0567 (7) | |
| H9A | −0.060895 | −0.008400 | 0.928134 | 0.068* | |
| C10A | −0.0481 (2) | 0.06996 (16) | 0.84087 (12) | 0.0433 (6) | |
| H10A | −0.127221 | 0.082528 | 0.835362 | 0.052* | |
| C11A | 0.02736 (19) | 0.10568 (14) | 0.79406 (11) | 0.0306 (5) | |
| H11A | 0.000747 | 0.144447 | 0.757541 | 0.037* | |
| C12A | 0.26047 (16) | 0.30269 (12) | 0.80976 (10) | 0.0222 (4) | |
| C13A | 0.20814 (18) | 0.36708 (14) | 0.76830 (11) | 0.0292 (4) | |
| H13A | 0.203599 | 0.362933 | 0.717838 | 0.035* | |
| C14A | 0.1626 (2) | 0.43709 (15) | 0.79939 (12) | 0.0358 (5) | |
| H14A | 0.126196 | 0.479605 | 0.770007 | 0.043* | |
| C15A | 0.1697 (2) | 0.44537 (15) | 0.87243 (12) | 0.0374 (5) | |
| H15A | 0.140423 | 0.494505 | 0.893829 | 0.045* | |
| C16A | 0.2199 (2) | 0.38141 (16) | 0.91441 (11) | 0.0369 (5) | |
| H16A | 0.224158 | 0.386125 | 0.964841 | 0.044* | |
| C17A | 0.26397 (19) | 0.31062 (14) | 0.88348 (10) | 0.0297 (4) | |
| H17A | 0.297182 | 0.266636 | 0.912960 | 0.036* | |
| C18A | 0.51525 (19) | 0.05483 (14) | 0.82424 (12) | 0.0343 (5) | |
| C19A | 0.5404 (2) | 0.06080 (17) | 0.89954 (12) | 0.0438 (6) | |
| H19A | 0.511702 | 0.106584 | 0.925091 | 0.053* | |
| C20A | 0.6054 (2) | 0.00245 (18) | 0.93782 (15) | 0.0520 (6) | |
| H20A | 0.619549 | 0.007599 | 0.988917 | 0.062* | |
| C21A | 0.6495 (2) | −0.06274 (17) | 0.90258 (15) | 0.0506 (7) | |
| H21A | 0.694726 | −0.102728 | 0.929014 | 0.061* | |
| C22A | 0.6279 (2) | −0.07035 (16) | 0.82751 (15) | 0.0451 (6) | |
| H22A | 0.659841 | −0.114413 | 0.802520 | 0.054* | |
| C23A | 0.5596 (2) | −0.01324 (15) | 0.78987 (13) | 0.0390 (5) | |
| O3A | 0.53096 (16) | −0.01728 (11) | 0.71594 (9) | 0.0487 (4) | |
| C24A | 0.5601 (3) | −0.09494 (19) | 0.67718 (15) | 0.0593 (7) | |
| H24A | 0.531866 | −0.092688 | 0.625301 | 0.089* | |
| H24B | 0.518130 | −0.159399 | 0.691013 | 0.089* | |
| H24C | 0.650153 | −0.085771 | 0.688765 | 0.089* | |
| O1B | 0.72932 (14) | 0.59540 (10) | 0.70807 (7) | 0.0325 (3) | |
| H1B | 0.667 (3) | 0.551 (2) | 0.6768 (16) | 0.075 (9)* | |
| O2B | 0.54682 (14) | 0.44673 (10) | 0.71982 (7) | 0.0300 (3) | |
| H2B | 0.496 (2) | 0.3930 (18) | 0.7227 (12) | 0.040 (7)* | |
| C1B | 0.68651 (18) | 0.59658 (13) | 0.77392 (10) | 0.0248 (4) | |
| C2B | 0.62450 (17) | 0.48732 (13) | 0.78901 (9) | 0.0239 (4) | |
| C3B | 0.54589 (17) | 0.50509 (14) | 0.84122 (10) | 0.0253 (4) | |
| H3BA | 0.598426 | 0.529602 | 0.889875 | 0.030* | |
| H3BB | 0.482352 | 0.443150 | 0.844548 | 0.030* | |
| C4B | 0.48449 (17) | 0.58350 (13) | 0.80977 (10) | 0.0264 (4) | |
| H4B | 0.407801 | 0.547362 | 0.773456 | 0.032* | |
| C5B | 0.57701 (18) | 0.64378 (14) | 0.76731 (10) | 0.0282 (4) | |
| H5BA | 0.535520 | 0.641122 | 0.716063 | 0.034* | |
| H5BB | 0.607415 | 0.714096 | 0.787718 | 0.034* | |
| C6B | 0.79924 (18) | 0.64960 (13) | 0.83207 (10) | 0.0279 (4) | |
| C7B | 0.7894 (2) | 0.70761 (14) | 0.89084 (11) | 0.0330 (5) | |
| H7B | 0.710772 | 0.716166 | 0.894287 | 0.040* | |
| C8B | 0.8941 (2) | 0.75301 (16) | 0.94442 (12) | 0.0463 (6) | |
| H8B | 0.886614 | 0.792497 | 0.984190 | 0.056* | |
| C9B | 1.0082 (2) | 0.74091 (17) | 0.94001 (15) | 0.0530 (7) | |
| H9B | 1.079536 | 0.772039 | 0.976589 | 0.064* | |
| C10B | 1.0188 (2) | 0.68325 (18) | 0.88210 (15) | 0.0515 (7) | |
| H10B | 1.097535 | 0.674489 | 0.879250 | 0.062* | |
| C11B | 0.91550 (19) | 0.63821 (16) | 0.82828 (13) | 0.0389 (5) | |
| H11B | 0.923985 | 0.599297 | 0.788524 | 0.047* | |
| C12B | 0.71105 (18) | 0.42414 (13) | 0.81557 (10) | 0.0255 (4) | |
| C13B | 0.77772 (19) | 0.43761 (15) | 0.88672 (11) | 0.0319 (5) | |
| H13B | 0.770028 | 0.488052 | 0.918968 | 0.038* | |
| C14B | 0.8550 (2) | 0.37885 (16) | 0.91130 (13) | 0.0419 (5) | |
| H14B | 0.900588 | 0.389782 | 0.959841 | 0.050* | |
| C15B | 0.8658 (2) | 0.30442 (17) | 0.86533 (13) | 0.0450 (6) | |
| H15B | 0.918043 | 0.263540 | 0.882187 | 0.054* | |
| C16B | 0.8005 (2) | 0.28981 (17) | 0.79511 (13) | 0.0436 (6) | |
| H16B | 0.807719 | 0.238573 | 0.763358 | 0.052* | |
| C17B | 0.7242 (2) | 0.34933 (15) | 0.77018 (11) | 0.0338 (5) | |
| H17B | 0.680232 | 0.338749 | 0.721309 | 0.041* | |
| C18B | 0.44390 (17) | 0.64346 (15) | 0.86390 (11) | 0.0317 (5) | |
| C19B | 0.4625 (2) | 0.63124 (17) | 0.93707 (12) | 0.0405 (5) | |
| H19B | 0.506993 | 0.585623 | 0.955254 | 0.049* | |
| C20B | 0.4182 (2) | 0.6835 (2) | 0.98427 (14) | 0.0542 (7) | |
| H20B | 0.430586 | 0.672705 | 1.033846 | 0.065* | |
| C21B | 0.3564 (2) | 0.7507 (2) | 0.95862 (15) | 0.0593 (8) | |
| H21B | 0.326291 | 0.787077 | 0.990813 | 0.071* | |
| C22B | 0.3371 (2) | 0.76666 (18) | 0.88654 (16) | 0.0520 (7) | |
| H22B | 0.295509 | 0.814533 | 0.869395 | 0.062* | |
| C23B | 0.37916 (19) | 0.71186 (15) | 0.83939 (12) | 0.0375 (5) | |
| O3B | 0.35836 (14) | 0.71818 (10) | 0.76626 (9) | 0.0427 (4) | |
| C24B | 0.2835 (2) | 0.78050 (18) | 0.73784 (17) | 0.0621 (8) | |
| H47D | 0.278101 | 0.780666 | 0.685806 | 0.093* | |
| H47E | 0.320979 | 0.848241 | 0.761150 | 0.093* | |
| H47F | 0.200007 | 0.755498 | 0.746985 | 0.093* | |
| O1C | 0.83623 (13) | 0.78847 (10) | 0.67276 (7) | 0.0293 (3) | |
| H1C | 0.810 (2) | 0.7296 (19) | 0.6878 (12) | 0.046 (7)* | |
| O2C | 1.00942 (13) | 0.92850 (10) | 0.64099 (8) | 0.0287 (3) | |
| H2C | 0.980 (2) | 0.9079 (18) | 0.6767 (14) | 0.051 (8)* | |
| C1C | 0.85364 (17) | 0.77202 (13) | 0.60124 (9) | 0.0224 (4) | |
| C2C | 0.91281 (17) | 0.87784 (13) | 0.57931 (9) | 0.0237 (4) | |
| C3C | 0.97825 (17) | 0.85444 (13) | 0.52145 (10) | 0.0241 (4) | |
| H3CA | 1.041397 | 0.914312 | 0.514056 | 0.029* | |
| H3CB | 0.917915 | 0.829337 | 0.475174 | 0.029* | |
| C4C | 1.04010 (17) | 0.77404 (13) | 0.55018 (10) | 0.0235 (4) | |
| H4C | 1.122322 | 0.809106 | 0.582118 | 0.028* | |
| C5C | 0.95607 (17) | 0.71870 (13) | 0.59948 (10) | 0.0246 (4) | |
| H5CA | 0.918233 | 0.648414 | 0.579981 | 0.029* | |
| H5CB | 1.006011 | 0.720663 | 0.648723 | 0.029* | |
| C6C | 0.72964 (17) | 0.71953 (12) | 0.55061 (9) | 0.0225 (4) | |
| C7C | 0.72397 (18) | 0.66404 (13) | 0.48685 (9) | 0.0246 (4) | |
| H7C | 0.798411 | 0.656154 | 0.475394 | 0.029* | |
| C8C | 0.61058 (19) | 0.62020 (15) | 0.43994 (11) | 0.0320 (5) | |
| H8C | 0.608086 | 0.582538 | 0.396759 | 0.038* | |
| C9C | 0.5012 (2) | 0.63106 (15) | 0.45574 (12) | 0.0372 (5) | |
| H9C | 0.423755 | 0.601828 | 0.423356 | 0.045* | |
| C10C | 0.50610 (19) | 0.68497 (16) | 0.51921 (12) | 0.0376 (5) | |
| H10C | 0.431508 | 0.692317 | 0.530778 | 0.045* | |
| C11C | 0.61908 (18) | 0.72833 (14) | 0.56603 (11) | 0.0301 (4) | |
| H11C | 0.620852 | 0.764836 | 0.609582 | 0.036* | |
| C12C | 0.82353 (17) | 0.94100 (13) | 0.55790 (10) | 0.0249 (4) | |
| C13C | 0.74574 (19) | 0.92723 (15) | 0.48961 (11) | 0.0304 (4) | |
| H13C | 0.746555 | 0.876044 | 0.455561 | 0.036* | |
| C14C | 0.6674 (2) | 0.98699 (16) | 0.47066 (12) | 0.0379 (5) | |
| H14C | 0.615020 | 0.976387 | 0.423859 | 0.045* | |
| C15C | 0.6646 (2) | 1.06201 (16) | 0.51930 (13) | 0.0417 (6) | |
| H15C | 0.611136 | 1.103224 | 0.506051 | 0.050* | |
| C16C | 0.7400 (2) | 1.07624 (16) | 0.58697 (14) | 0.0438 (6) | |
| H16C | 0.738493 | 1.127377 | 0.620812 | 0.053* | |
| C17C | 0.81854 (19) | 1.01628 (15) | 0.60615 (12) | 0.0350 (5) | |
| H17C | 0.869919 | 1.026903 | 0.653229 | 0.042* | |
| C18C | 1.06489 (17) | 0.70730 (13) | 0.49336 (10) | 0.0251 (4) | |
| C19C | 1.03585 (18) | 0.71550 (14) | 0.41988 (10) | 0.0285 (4) | |
| H19C | 0.994730 | 0.763803 | 0.403130 | 0.034* | |
| C20C | 1.06512 (19) | 0.65517 (16) | 0.37003 (11) | 0.0343 (5) | |
| H20C | 1.044696 | 0.662858 | 0.320080 | 0.041* | |
| C21C | 1.12357 (19) | 0.58454 (15) | 0.39328 (11) | 0.0348 (5) | |
| H21C | 1.142862 | 0.542847 | 0.359249 | 0.042* | |
| C22C | 1.15471 (18) | 0.57361 (14) | 0.46625 (11) | 0.0313 (5) | |
| H22C | 1.194781 | 0.524405 | 0.482294 | 0.038* | |
| C23C | 1.12666 (18) | 0.63544 (14) | 0.51566 (10) | 0.0271 (4) | |
| O3C | 1.15809 (14) | 0.63245 (10) | 0.58874 (7) | 0.0342 (3) | |
| C24C | 1.2122 (2) | 0.55618 (16) | 0.61470 (12) | 0.0391 (5) | |
| H24G | 1.229764 | 0.562486 | 0.667487 | 0.059* | |
| H24H | 1.289720 | 0.562436 | 0.598343 | 0.059* | |
| H24I | 1.154227 | 0.491171 | 0.596126 | 0.059* |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1A | 0.0318 (8) | 0.0254 (7) | 0.0242 (7) | 0.0063 (6) | −0.0022 (6) | −0.0010 (6) |
| O2A | 0.0326 (8) | 0.0310 (7) | 0.0230 (7) | 0.0055 (6) | 0.0067 (6) | 0.0013 (6) |
| C1A | 0.0277 (10) | 0.0206 (9) | 0.0257 (9) | 0.0081 (8) | −0.0019 (8) | −0.0014 (8) |
| C2A | 0.0257 (10) | 0.0220 (9) | 0.0220 (9) | 0.0039 (8) | 0.0047 (8) | 0.0014 (7) |
| C3A | 0.0255 (10) | 0.0258 (10) | 0.0287 (10) | 0.0075 (8) | 0.0038 (8) | −0.0003 (8) |
| C4A | 0.0314 (11) | 0.0308 (11) | 0.0361 (11) | 0.0103 (9) | 0.0067 (9) | −0.0002 (9) |
| C5A | 0.0357 (12) | 0.0299 (11) | 0.0388 (12) | 0.0137 (9) | −0.0007 (9) | −0.0065 (9) |
| C6A | 0.0324 (11) | 0.0156 (9) | 0.0294 (10) | 0.0023 (8) | −0.0014 (8) | 0.0017 (8) |
| C7A | 0.0379 (13) | 0.0329 (11) | 0.0466 (13) | 0.0018 (10) | −0.0010 (11) | 0.0178 (10) |
| C8A | 0.0536 (17) | 0.0531 (15) | 0.0540 (15) | −0.0015 (13) | 0.0012 (13) | 0.0286 (13) |
| C9A | 0.0576 (17) | 0.0534 (15) | 0.0511 (15) | −0.0071 (13) | 0.0204 (13) | 0.0177 (13) |
| C10A | 0.0410 (13) | 0.0377 (12) | 0.0474 (13) | 0.0014 (10) | 0.0132 (11) | 0.0037 (11) |
| C11A | 0.0356 (11) | 0.0205 (9) | 0.0323 (11) | 0.0033 (8) | 0.0048 (9) | 0.0026 (8) |
| C12A | 0.0193 (9) | 0.0178 (8) | 0.0265 (9) | 0.0006 (7) | 0.0041 (8) | 0.0001 (7) |
| C13A | 0.0306 (11) | 0.0288 (10) | 0.0276 (10) | 0.0085 (9) | 0.0042 (8) | 0.0028 (8) |
| C14A | 0.0361 (12) | 0.0292 (11) | 0.0445 (12) | 0.0145 (9) | 0.0060 (10) | 0.0081 (9) |
| C15A | 0.0372 (12) | 0.0299 (11) | 0.0491 (13) | 0.0132 (9) | 0.0145 (10) | −0.0028 (10) |
| C16A | 0.0453 (13) | 0.0397 (12) | 0.0285 (11) | 0.0114 (10) | 0.0159 (10) | −0.0008 (9) |
| C17A | 0.0343 (11) | 0.0275 (10) | 0.0291 (10) | 0.0102 (9) | 0.0086 (9) | 0.0055 (8) |
| C18A | 0.0247 (10) | 0.0250 (10) | 0.0527 (13) | 0.0058 (8) | 0.0084 (10) | 0.0046 (9) |
| C19A | 0.0422 (13) | 0.0419 (13) | 0.0437 (13) | 0.0168 (11) | −0.0042 (11) | −0.0029 (11) |
| C20A | 0.0526 (15) | 0.0415 (13) | 0.0604 (16) | 0.0182 (12) | 0.0019 (13) | 0.0038 (12) |
| C21A | 0.0363 (13) | 0.0368 (13) | 0.0756 (18) | 0.0156 (11) | −0.0034 (12) | 0.0113 (12) |
| C22A | 0.0370 (13) | 0.0309 (11) | 0.0714 (17) | 0.0156 (10) | 0.0123 (12) | 0.0049 (11) |
| C23A | 0.0310 (12) | 0.0296 (11) | 0.0590 (15) | 0.0071 (9) | 0.0165 (11) | 0.0087 (10) |
| O3A | 0.0668 (11) | 0.0407 (9) | 0.0534 (10) | 0.0282 (8) | 0.0288 (9) | 0.0082 (8) |
| C24A | 0.085 (2) | 0.0468 (15) | 0.0678 (17) | 0.0359 (14) | 0.0431 (16) | 0.0106 (13) |
| O1B | 0.0421 (9) | 0.0314 (8) | 0.0265 (7) | 0.0082 (7) | 0.0142 (7) | 0.0094 (6) |
| O2B | 0.0366 (8) | 0.0254 (7) | 0.0219 (7) | 0.0020 (7) | 0.0007 (6) | 0.0031 (6) |
| C1B | 0.0299 (10) | 0.0239 (9) | 0.0218 (9) | 0.0069 (8) | 0.0079 (8) | 0.0077 (8) |
| C2B | 0.0253 (10) | 0.0245 (9) | 0.0190 (9) | 0.0036 (8) | 0.0020 (8) | 0.0038 (7) |
| C3B | 0.0228 (10) | 0.0268 (9) | 0.0238 (9) | 0.0028 (8) | 0.0040 (8) | 0.0042 (8) |
| C4B | 0.0222 (10) | 0.0257 (10) | 0.0276 (10) | 0.0037 (8) | 0.0008 (8) | 0.0007 (8) |
| C5B | 0.0290 (11) | 0.0252 (10) | 0.0283 (10) | 0.0067 (8) | 0.0012 (8) | 0.0061 (8) |
| C6B | 0.0264 (10) | 0.0235 (9) | 0.0315 (10) | 0.0022 (8) | 0.0055 (8) | 0.0109 (8) |
| C7B | 0.0352 (12) | 0.0269 (10) | 0.0316 (11) | 0.0018 (9) | 0.0034 (9) | 0.0050 (9) |
| C8B | 0.0531 (16) | 0.0318 (12) | 0.0383 (12) | −0.0044 (11) | −0.0050 (11) | 0.0047 (10) |
| C9B | 0.0378 (14) | 0.0368 (13) | 0.0629 (17) | −0.0092 (11) | −0.0157 (12) | 0.0177 (12) |
| C10B | 0.0265 (12) | 0.0425 (13) | 0.0800 (19) | 0.0035 (10) | 0.0038 (12) | 0.0201 (14) |
| C11B | 0.0295 (12) | 0.0331 (11) | 0.0535 (14) | 0.0051 (9) | 0.0101 (10) | 0.0152 (10) |
| C12B | 0.0272 (10) | 0.0220 (9) | 0.0281 (10) | 0.0033 (8) | 0.0108 (8) | 0.0087 (8) |
| C13B | 0.0339 (11) | 0.0291 (10) | 0.0329 (11) | 0.0101 (9) | 0.0051 (9) | 0.0067 (9) |
| C14B | 0.0397 (13) | 0.0437 (13) | 0.0422 (13) | 0.0165 (11) | 0.0010 (10) | 0.0119 (11) |
| C15B | 0.0442 (14) | 0.0432 (13) | 0.0575 (15) | 0.0252 (11) | 0.0143 (12) | 0.0177 (11) |
| C16B | 0.0499 (14) | 0.0401 (13) | 0.0519 (14) | 0.0224 (11) | 0.0234 (12) | 0.0070 (11) |
| C17B | 0.0385 (12) | 0.0334 (11) | 0.0334 (11) | 0.0109 (9) | 0.0145 (9) | 0.0071 (9) |
| C18B | 0.0171 (9) | 0.0313 (10) | 0.0404 (11) | 0.0003 (8) | 0.0024 (8) | −0.0065 (9) |
| C19B | 0.0284 (11) | 0.0497 (13) | 0.0378 (12) | 0.0044 (10) | 0.0053 (9) | −0.0084 (10) |
| C20B | 0.0309 (13) | 0.0759 (18) | 0.0469 (14) | 0.0026 (13) | 0.0090 (11) | −0.0200 (13) |
| C21B | 0.0296 (13) | 0.0715 (18) | 0.0677 (18) | 0.0051 (13) | 0.0097 (12) | −0.0353 (15) |
| C22B | 0.0239 (12) | 0.0432 (13) | 0.084 (2) | 0.0084 (10) | 0.0054 (12) | −0.0188 (13) |
| C23B | 0.0214 (10) | 0.0333 (11) | 0.0500 (13) | 0.0019 (9) | 0.0000 (9) | −0.0080 (10) |
| O3B | 0.0346 (8) | 0.0324 (8) | 0.0584 (10) | 0.0164 (7) | −0.0051 (7) | 0.0023 (7) |
| C24B | 0.0457 (15) | 0.0407 (13) | 0.091 (2) | 0.0219 (12) | −0.0171 (14) | −0.0009 (14) |
| O1C | 0.0412 (8) | 0.0262 (7) | 0.0194 (6) | 0.0047 (6) | 0.0095 (6) | 0.0031 (6) |
| O2C | 0.0288 (8) | 0.0240 (7) | 0.0265 (7) | 0.0002 (6) | 0.0001 (6) | −0.0013 (6) |
| C1C | 0.0286 (10) | 0.0207 (9) | 0.0166 (8) | 0.0040 (8) | 0.0055 (7) | 0.0028 (7) |
| C2C | 0.0254 (10) | 0.0200 (9) | 0.0219 (9) | 0.0009 (7) | 0.0034 (8) | 0.0001 (7) |
| C3C | 0.0254 (10) | 0.0220 (9) | 0.0253 (9) | 0.0044 (8) | 0.0087 (8) | 0.0074 (8) |
| C4C | 0.0237 (10) | 0.0222 (9) | 0.0238 (9) | 0.0050 (8) | 0.0044 (8) | 0.0046 (7) |
| C5C | 0.0275 (10) | 0.0226 (9) | 0.0219 (9) | 0.0052 (8) | 0.0028 (8) | 0.0052 (7) |
| C6C | 0.0267 (10) | 0.0170 (8) | 0.0238 (9) | 0.0034 (7) | 0.0079 (8) | 0.0055 (7) |
| C7C | 0.0280 (10) | 0.0232 (9) | 0.0233 (9) | 0.0072 (8) | 0.0068 (8) | 0.0039 (8) |
| C8C | 0.0363 (12) | 0.0303 (10) | 0.0258 (10) | 0.0071 (9) | 0.0016 (9) | −0.0019 (8) |
| C9C | 0.0270 (11) | 0.0364 (11) | 0.0399 (12) | 0.0019 (9) | −0.0020 (9) | −0.0014 (10) |
| C10C | 0.0250 (11) | 0.0389 (12) | 0.0487 (13) | 0.0054 (9) | 0.0124 (10) | 0.0034 (10) |
| C11C | 0.0321 (11) | 0.0276 (10) | 0.0306 (10) | 0.0052 (9) | 0.0112 (9) | −0.0003 (8) |
| C12C | 0.0243 (10) | 0.0189 (9) | 0.0300 (10) | 0.0008 (7) | 0.0089 (8) | 0.0041 (8) |
| C13C | 0.0346 (11) | 0.0303 (10) | 0.0298 (10) | 0.0126 (9) | 0.0100 (9) | 0.0046 (8) |
| C14C | 0.0363 (12) | 0.0428 (12) | 0.0394 (12) | 0.0174 (10) | 0.0090 (10) | 0.0123 (10) |
| C15C | 0.0364 (12) | 0.0345 (12) | 0.0629 (15) | 0.0186 (10) | 0.0178 (12) | 0.0114 (11) |
| C16C | 0.0375 (13) | 0.0321 (11) | 0.0625 (16) | 0.0106 (10) | 0.0140 (12) | −0.0091 (11) |
| C17C | 0.0307 (11) | 0.0310 (11) | 0.0402 (12) | 0.0035 (9) | 0.0087 (9) | −0.0063 (9) |
| C18C | 0.0217 (10) | 0.0245 (9) | 0.0277 (10) | 0.0028 (8) | 0.0062 (8) | 0.0052 (8) |
| C19C | 0.0265 (10) | 0.0297 (10) | 0.0297 (10) | 0.0070 (8) | 0.0074 (8) | 0.0066 (8) |
| C20C | 0.0331 (11) | 0.0415 (12) | 0.0275 (10) | 0.0072 (10) | 0.0090 (9) | 0.0035 (9) |
| C21C | 0.0340 (12) | 0.0366 (11) | 0.0339 (11) | 0.0082 (9) | 0.0115 (9) | −0.0051 (9) |
| C22C | 0.0267 (10) | 0.0274 (10) | 0.0408 (12) | 0.0090 (8) | 0.0080 (9) | 0.0039 (9) |
| C23C | 0.0249 (10) | 0.0263 (10) | 0.0287 (10) | 0.0046 (8) | 0.0056 (8) | 0.0042 (8) |
| O3C | 0.0447 (9) | 0.0330 (8) | 0.0287 (7) | 0.0206 (7) | 0.0034 (6) | 0.0059 (6) |
| C24C | 0.0460 (13) | 0.0355 (12) | 0.0407 (12) | 0.0205 (10) | 0.0065 (10) | 0.0121 (10) |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Geometric parameters (Å, º)
| O1A—C1A | 1.431 (2) | C11B—H11B | 0.9500 |
| O1A—H1A | 0.85 (3) | C12B—C17B | 1.388 (3) |
| O2A—C2A | 1.439 (2) | C12B—C13B | 1.393 (3) |
| O2A—H2A | 0.88 (3) | C13B—C14B | 1.385 (3) |
| C1A—C6A | 1.519 (3) | C13B—H13B | 0.9500 |
| C1A—C5A | 1.550 (3) | C14B—C15B | 1.380 (3) |
| C1A—C2A | 1.572 (2) | C14B—H14B | 0.9500 |
| C2A—C12A | 1.521 (2) | C15B—C16B | 1.372 (3) |
| C2A—C3A | 1.523 (3) | C15B—H15B | 0.9500 |
| C3A—C4A | 1.528 (3) | C16B—C17B | 1.387 (3) |
| C3A—H3AA | 0.9900 | C16B—H16B | 0.9500 |
| C3A—H3AB | 0.9900 | C17B—H17B | 0.9500 |
| C4A—C18A | 1.510 (3) | C18B—C19B | 1.391 (3) |
| C4A—C5A | 1.567 (3) | C18B—C23B | 1.396 (3) |
| C4A—H4A | 1.0000 | C19B—C20B | 1.385 (3) |
| C5A—H5AA | 0.9900 | C19B—H19B | 0.9500 |
| C5A—H5AB | 0.9900 | C20B—C21B | 1.367 (4) |
| C6A—C7A | 1.399 (3) | C20B—H20B | 0.9500 |
| C6A—C11A | 1.399 (3) | C21B—C22B | 1.382 (4) |
| C7A—C8A | 1.376 (4) | C21B—H21B | 0.9500 |
| C7A—H7A | 0.9500 | C22B—C23B | 1.390 (3) |
| C8A—C9A | 1.375 (4) | C22B—H22B | 0.9500 |
| C8A—H8A | 0.9500 | C23B—O3B | 1.375 (3) |
| C9A—C10A | 1.385 (3) | O3B—C24B | 1.423 (3) |
| C9A—H9A | 0.9500 | C24B—H47D | 0.9800 |
| C10A—C11A | 1.381 (3) | C24B—H47E | 0.9800 |
| C10A—H10A | 0.9500 | C24B—H47F | 0.9800 |
| C11A—H11A | 0.9500 | O1C—C1C | 1.433 (2) |
| C12A—C13A | 1.394 (3) | O1C—H1C | 0.88 (3) |
| C12A—C17A | 1.395 (3) | O2C—C2C | 1.451 (2) |
| C13A—C14A | 1.387 (3) | O2C—H2C | 0.85 (3) |
| C13A—H13A | 0.9500 | C1C—C6C | 1.526 (2) |
| C14A—C15A | 1.375 (3) | C1C—C5C | 1.547 (3) |
| C14A—H14A | 0.9500 | C1C—C2C | 1.573 (2) |
| C15A—C16A | 1.383 (3) | C2C—C3C | 1.518 (3) |
| C15A—H15A | 0.9500 | C2C—C12C | 1.523 (3) |
| C16A—C17A | 1.383 (3) | C3C—C4C | 1.541 (2) |
| C16A—H16A | 0.9500 | C3C—H3CA | 0.9900 |
| C17A—H17A | 0.9500 | C3C—H3CB | 0.9900 |
| C18A—C23A | 1.388 (3) | C4C—C18C | 1.517 (3) |
| C18A—C19A | 1.399 (3) | C4C—C5C | 1.561 (3) |
| C19A—C20A | 1.377 (3) | C4C—H4C | 1.0000 |
| C19A—H19A | 0.9500 | C5C—H5CA | 0.9900 |
| C20A—C21A | 1.365 (3) | C5C—H5CB | 0.9900 |
| C20A—H20A | 0.9500 | C6C—C11C | 1.386 (3) |
| C21A—C22A | 1.395 (4) | C6C—C7C | 1.395 (3) |
| C21A—H21A | 0.9500 | C7C—C8C | 1.389 (3) |
| C22A—C23A | 1.381 (3) | C7C—H7C | 0.9500 |
| C22A—H22A | 0.9500 | C8C—C9C | 1.385 (3) |
| C23A—O3A | 1.375 (3) | C8C—H8C | 0.9500 |
| O3A—C24A | 1.435 (3) | C9C—C10C | 1.382 (3) |
| C24A—H24A | 0.9800 | C9C—H9C | 0.9500 |
| C24A—H24B | 0.9800 | C10C—C11C | 1.384 (3) |
| C24A—H24C | 0.9800 | C10C—H10C | 0.9500 |
| O1B—C1B | 1.434 (2) | C11C—H11C | 0.9500 |
| O1B—H1B | 0.90 (3) | C12C—C17C | 1.390 (3) |
| O2B—C2B | 1.433 (2) | C12C—C13C | 1.394 (3) |
| O2B—H2B | 0.83 (2) | C13C—C14C | 1.384 (3) |
| C1B—C6B | 1.517 (3) | C13C—H13C | 0.9500 |
| C1B—C5B | 1.545 (3) | C14C—C15C | 1.383 (3) |
| C1B—C2B | 1.576 (3) | C14C—H14C | 0.9500 |
| C2B—C12B | 1.518 (3) | C15C—C16C | 1.373 (3) |
| C2B—C3B | 1.519 (3) | C15C—H15C | 0.9500 |
| C3B—C4B | 1.530 (3) | C16C—C17C | 1.388 (3) |
| C3B—H3BA | 0.9900 | C16C—H16C | 0.9500 |
| C3B—H3BB | 0.9900 | C17C—H17C | 0.9500 |
| C4B—C18B | 1.518 (3) | C18C—C19C | 1.388 (3) |
| C4B—C5B | 1.555 (3) | C18C—C23C | 1.405 (3) |
| C4B—H4B | 1.0000 | C19C—C20C | 1.391 (3) |
| C5B—H5BA | 0.9900 | C19C—H19C | 0.9500 |
| C5B—H5BB | 0.9900 | C20C—C21C | 1.371 (3) |
| C6B—C11B | 1.392 (3) | C20C—H20C | 0.9500 |
| C6B—C7B | 1.396 (3) | C21C—C22C | 1.388 (3) |
| C7B—C8B | 1.392 (3) | C21C—H21C | 0.9500 |
| C7B—H7B | 0.9500 | C22C—C23C | 1.391 (3) |
| C8B—C9B | 1.374 (4) | C22C—H22C | 0.9500 |
| C8B—H8B | 0.9500 | C23C—O3C | 1.370 (2) |
| C9B—C10B | 1.383 (4) | O3C—C24C | 1.425 (2) |
| C9B—H9B | 0.9500 | C24C—H24G | 0.9800 |
| C10B—C11B | 1.384 (3) | C24C—H24H | 0.9800 |
| C10B—H10B | 0.9500 | C24C—H24I | 0.9800 |
| C1A—O1A—H1A | 112.0 (19) | C10B—C11B—C6B | 120.4 (2) |
| C2A—O2A—H2A | 107.8 (17) | C10B—C11B—H11B | 119.8 |
| O1A—C1A—C6A | 110.11 (15) | C6B—C11B—H11B | 119.8 |
| O1A—C1A—C5A | 111.34 (15) | C17B—C12B—C13B | 117.69 (18) |
| C6A—C1A—C5A | 113.96 (16) | C17B—C12B—C2B | 121.09 (17) |
| O1A—C1A—C2A | 106.48 (14) | C13B—C12B—C2B | 121.20 (17) |
| C6A—C1A—C2A | 111.94 (15) | C14B—C13B—C12B | 121.2 (2) |
| C5A—C1A—C2A | 102.56 (15) | C14B—C13B—H13B | 119.4 |
| O2A—C2A—C12A | 109.77 (14) | C12B—C13B—H13B | 119.4 |
| O2A—C2A—C3A | 106.20 (15) | C15B—C14B—C13B | 120.0 (2) |
| C12A—C2A—C3A | 115.04 (15) | C15B—C14B—H14B | 120.0 |
| O2A—C2A—C1A | 106.81 (14) | C13B—C14B—H14B | 120.0 |
| C12A—C2A—C1A | 115.93 (15) | C16B—C15B—C14B | 119.6 (2) |
| C3A—C2A—C1A | 102.28 (14) | C16B—C15B—H15B | 120.2 |
| C2A—C3A—C4A | 104.60 (15) | C14B—C15B—H15B | 120.2 |
| C2A—C3A—H3AA | 110.8 | C15B—C16B—C17B | 120.5 (2) |
| C4A—C3A—H3AA | 110.8 | C15B—C16B—H16B | 119.8 |
| C2A—C3A—H3AB | 110.8 | C17B—C16B—H16B | 119.8 |
| C4A—C3A—H3AB | 110.8 | C16B—C17B—C12B | 121.0 (2) |
| H3AA—C3A—H3AB | 108.9 | C16B—C17B—H17B | 119.5 |
| C18A—C4A—C3A | 115.73 (17) | C12B—C17B—H17B | 119.5 |
| C18A—C4A—C5A | 114.89 (17) | C19B—C18B—C23B | 117.2 (2) |
| C3A—C4A—C5A | 104.00 (16) | C19B—C18B—C4B | 123.68 (18) |
| C18A—C4A—H4A | 107.2 | C23B—C18B—C4B | 119.02 (19) |
| C3A—C4A—H4A | 107.2 | C20B—C19B—C18B | 122.1 (2) |
| C5A—C4A—H4A | 107.2 | C20B—C19B—H19B | 119.0 |
| C1A—C5A—C4A | 107.50 (15) | C18B—C19B—H19B | 119.0 |
| C1A—C5A—H5AA | 110.2 | C21B—C20B—C19B | 119.2 (3) |
| C4A—C5A—H5AA | 110.2 | C21B—C20B—H20B | 120.4 |
| C1A—C5A—H5AB | 110.2 | C19B—C20B—H20B | 120.4 |
| C4A—C5A—H5AB | 110.2 | C20B—C21B—C22B | 121.0 (2) |
| H5AA—C5A—H5AB | 108.5 | C20B—C21B—H21B | 119.5 |
| C7A—C6A—C11A | 117.7 (2) | C22B—C21B—H21B | 119.5 |
| C7A—C6A—C1A | 122.19 (19) | C21B—C22B—C23B | 119.3 (2) |
| C11A—C6A—C1A | 120.06 (16) | C21B—C22B—H22B | 120.4 |
| C8A—C7A—C6A | 120.8 (2) | C23B—C22B—H22B | 120.4 |
| C8A—C7A—H7A | 119.6 | O3B—C23B—C22B | 123.7 (2) |
| C6A—C7A—H7A | 119.6 | O3B—C23B—C18B | 115.09 (18) |
| C9A—C8A—C7A | 120.9 (2) | C22B—C23B—C18B | 121.2 (2) |
| C9A—C8A—H8A | 119.6 | C23B—O3B—C24B | 117.21 (19) |
| C7A—C8A—H8A | 119.6 | O3B—C24B—H47D | 109.5 |
| C8A—C9A—C10A | 119.3 (2) | O3B—C24B—H47E | 109.5 |
| C8A—C9A—H9A | 120.3 | H47D—C24B—H47E | 109.5 |
| C10A—C9A—H9A | 120.3 | O3B—C24B—H47F | 109.5 |
| C11A—C10A—C9A | 120.3 (2) | H47D—C24B—H47F | 109.5 |
| C11A—C10A—H10A | 119.8 | H47E—C24B—H47F | 109.5 |
| C9A—C10A—H10A | 119.8 | C1C—O1C—H1C | 106.9 (15) |
| C10A—C11A—C6A | 120.88 (19) | C2C—O2C—H2C | 103.6 (18) |
| C10A—C11A—H11A | 119.6 | O1C—C1C—C6C | 110.23 (15) |
| C6A—C11A—H11A | 119.6 | O1C—C1C—C5C | 112.18 (14) |
| C13A—C12A—C17A | 117.48 (17) | C6C—C1C—C5C | 113.42 (14) |
| C13A—C12A—C2A | 120.01 (16) | O1C—C1C—C2C | 105.54 (14) |
| C17A—C12A—C2A | 122.47 (16) | C6C—C1C—C2C | 112.39 (14) |
| C14A—C13A—C12A | 121.18 (18) | C5C—C1C—C2C | 102.62 (14) |
| C14A—C13A—H13A | 119.4 | O2C—C2C—C3C | 106.63 (15) |
| C12A—C13A—H13A | 119.4 | O2C—C2C—C12C | 109.57 (14) |
| C15A—C14A—C13A | 120.44 (19) | C3C—C2C—C12C | 115.35 (15) |
| C15A—C14A—H14A | 119.8 | O2C—C2C—C1C | 106.13 (14) |
| C13A—C14A—H14A | 119.8 | C3C—C2C—C1C | 102.59 (14) |
| C14A—C15A—C16A | 119.29 (19) | C12C—C2C—C1C | 115.77 (15) |
| C14A—C15A—H15A | 120.4 | C2C—C3C—C4C | 104.93 (14) |
| C16A—C15A—H15A | 120.4 | C2C—C3C—H3CA | 110.8 |
| C15A—C16A—C17A | 120.44 (19) | C4C—C3C—H3CA | 110.8 |
| C15A—C16A—H16A | 119.8 | C2C—C3C—H3CB | 110.8 |
| C17A—C16A—H16A | 119.8 | C4C—C3C—H3CB | 110.8 |
| C16A—C17A—C12A | 121.13 (18) | H3CA—C3C—H3CB | 108.8 |
| C16A—C17A—H17A | 119.4 | C18C—C4C—C3C | 115.56 (15) |
| C12A—C17A—H17A | 119.4 | C18C—C4C—C5C | 114.86 (15) |
| C23A—C18A—C19A | 116.3 (2) | C3C—C4C—C5C | 104.57 (14) |
| C23A—C18A—C4A | 120.1 (2) | C18C—C4C—H4C | 107.1 |
| C19A—C18A—C4A | 123.56 (19) | C3C—C4C—H4C | 107.1 |
| C20A—C19A—C18A | 122.1 (2) | C5C—C4C—H4C | 107.1 |
| C20A—C19A—H19A | 118.9 | C1C—C5C—C4C | 107.41 (14) |
| C18A—C19A—H19A | 118.9 | C1C—C5C—H5CA | 110.2 |
| C21A—C20A—C19A | 120.2 (3) | C4C—C5C—H5CA | 110.2 |
| C21A—C20A—H20A | 119.9 | C1C—C5C—H5CB | 110.2 |
| C19A—C20A—H20A | 119.9 | C4C—C5C—H5CB | 110.2 |
| C20A—C21A—C22A | 119.7 (2) | H5CA—C5C—H5CB | 108.5 |
| C20A—C21A—H21A | 120.2 | C11C—C6C—C7C | 118.08 (17) |
| C22A—C21A—H21A | 120.2 | C11C—C6C—C1C | 120.41 (16) |
| C23A—C22A—C21A | 119.4 (2) | C7C—C6C—C1C | 121.49 (17) |
| C23A—C22A—H22A | 120.3 | C8C—C7C—C6C | 120.68 (18) |
| C21A—C22A—H22A | 120.3 | C8C—C7C—H7C | 119.7 |
| O3A—C23A—C22A | 123.7 (2) | C6C—C7C—H7C | 119.7 |
| O3A—C23A—C18A | 114.08 (19) | C9C—C8C—C7C | 120.42 (19) |
| C22A—C23A—C18A | 122.3 (2) | C9C—C8C—H8C | 119.8 |
| C23A—O3A—C24A | 116.64 (18) | C7C—C8C—H8C | 119.8 |
| O3A—C24A—H24A | 109.5 | C10C—C9C—C8C | 119.14 (19) |
| O3A—C24A—H24B | 109.5 | C10C—C9C—H9C | 120.4 |
| H24A—C24A—H24B | 109.5 | C8C—C9C—H9C | 120.4 |
| O3A—C24A—H24C | 109.5 | C9C—C10C—C11C | 120.4 (2) |
| H24A—C24A—H24C | 109.5 | C9C—C10C—H10C | 119.8 |
| H24B—C24A—H24C | 109.5 | C11C—C10C—H10C | 119.8 |
| C1B—O1B—H1B | 104.6 (19) | C10C—C11C—C6C | 121.27 (19) |
| C2B—O2B—H2B | 110.9 (16) | C10C—C11C—H11C | 119.4 |
| O1B—C1B—C6B | 106.18 (15) | C6C—C11C—H11C | 119.4 |
| O1B—C1B—C5B | 111.73 (14) | C17C—C12C—C13C | 117.52 (18) |
| C6B—C1B—C5B | 113.99 (15) | C17C—C12C—C2C | 120.56 (17) |
| O1B—C1B—C2B | 110.01 (14) | C13C—C12C—C2C | 121.92 (16) |
| C6B—C1B—C2B | 113.17 (14) | C14C—C13C—C12C | 121.01 (19) |
| C5B—C1B—C2B | 101.86 (15) | C14C—C13C—H13C | 119.5 |
| O2B—C2B—C12B | 111.05 (15) | C12C—C13C—H13C | 119.5 |
| O2B—C2B—C3B | 110.25 (15) | C15C—C14C—C13C | 120.5 (2) |
| C12B—C2B—C3B | 114.29 (15) | C15C—C14C—H14C | 119.7 |
| O2B—C2B—C1B | 101.57 (14) | C13C—C14C—H14C | 119.7 |
| C12B—C2B—C1B | 117.05 (15) | C16C—C15C—C14C | 119.24 (19) |
| C3B—C2B—C1B | 101.58 (14) | C16C—C15C—H15C | 120.4 |
| C2B—C3B—C4B | 105.00 (15) | C14C—C15C—H15C | 120.4 |
| C2B—C3B—H3BA | 110.7 | C15C—C16C—C17C | 120.3 (2) |
| C4B—C3B—H3BA | 110.7 | C15C—C16C—H16C | 119.8 |
| C2B—C3B—H3BB | 110.7 | C17C—C16C—H16C | 119.8 |
| C4B—C3B—H3BB | 110.7 | C16C—C17C—C12C | 121.4 (2) |
| H3BA—C3B—H3BB | 108.8 | C16C—C17C—H17C | 119.3 |
| C18B—C4B—C3B | 114.93 (16) | C12C—C17C—H17C | 119.3 |
| C18B—C4B—C5B | 116.17 (16) | C19C—C18C—C23C | 116.97 (17) |
| C3B—C4B—C5B | 104.48 (15) | C19C—C18C—C4C | 124.14 (16) |
| C18B—C4B—H4B | 106.9 | C23C—C18C—C4C | 118.81 (16) |
| C3B—C4B—H4B | 106.9 | C18C—C19C—C20C | 122.01 (18) |
| C5B—C4B—H4B | 106.9 | C18C—C19C—H19C | 119.0 |
| C1B—C5B—C4B | 107.35 (14) | C20C—C19C—H19C | 119.0 |
| C1B—C5B—H5BA | 110.2 | C21C—C20C—C19C | 119.72 (19) |
| C4B—C5B—H5BA | 110.2 | C21C—C20C—H20C | 120.1 |
| C1B—C5B—H5BB | 110.2 | C19C—C20C—H20C | 120.1 |
| C4B—C5B—H5BB | 110.2 | C20C—C21C—C22C | 120.40 (19) |
| H5BA—C5B—H5BB | 108.5 | C20C—C21C—H21C | 119.8 |
| C11B—C6B—C7B | 118.68 (19) | C22C—C21C—H21C | 119.8 |
| C11B—C6B—C1B | 119.53 (18) | C21C—C22C—C23C | 119.33 (18) |
| C7B—C6B—C1B | 121.76 (18) | C21C—C22C—H22C | 120.3 |
| C8B—C7B—C6B | 120.4 (2) | C23C—C22C—H22C | 120.3 |
| C8B—C7B—H7B | 119.8 | O3C—C23C—C22C | 123.31 (17) |
| C6B—C7B—H7B | 119.8 | O3C—C23C—C18C | 115.13 (16) |
| C9B—C8B—C7B | 120.2 (2) | C22C—C23C—C18C | 121.55 (18) |
| C9B—C8B—H8B | 119.9 | C23C—O3C—C24C | 117.90 (15) |
| C7B—C8B—H8B | 119.9 | O3C—C24C—H24G | 109.5 |
| C8B—C9B—C10B | 119.8 (2) | O3C—C24C—H24H | 109.5 |
| C8B—C9B—H9B | 120.1 | H24G—C24C—H24H | 109.5 |
| C10B—C9B—H9B | 120.1 | O3C—C24C—H24I | 109.5 |
| C9B—C10B—C11B | 120.5 (2) | H24G—C24C—H24I | 109.5 |
| C9B—C10B—H10B | 119.7 | H24H—C24C—H24I | 109.5 |
| C11B—C10B—H10B | 119.7 | ||
| O1A—C1A—C2A—O2A | −43.86 (18) | C1B—C6B—C11B—C10B | −177.79 (18) |
| C6A—C1A—C2A—O2A | −164.24 (14) | O2B—C2B—C12B—C17B | 11.0 (2) |
| C5A—C1A—C2A—O2A | 73.19 (17) | C3B—C2B—C12B—C17B | 136.46 (19) |
| O1A—C1A—C2A—C12A | 78.81 (19) | C1B—C2B—C12B—C17B | −105.0 (2) |
| C6A—C1A—C2A—C12A | −41.6 (2) | O2B—C2B—C12B—C13B | −167.48 (17) |
| C5A—C1A—C2A—C12A | −164.14 (16) | C3B—C2B—C12B—C13B | −42.0 (2) |
| O1A—C1A—C2A—C3A | −155.21 (15) | C1B—C2B—C12B—C13B | 76.6 (2) |
| C6A—C1A—C2A—C3A | 84.41 (17) | C17B—C12B—C13B—C14B | 0.3 (3) |
| C5A—C1A—C2A—C3A | −38.16 (18) | C2B—C12B—C13B—C14B | 178.85 (19) |
| O2A—C2A—C3A—C4A | −67.63 (18) | C12B—C13B—C14B—C15B | −0.9 (3) |
| C12A—C2A—C3A—C4A | 170.73 (16) | C13B—C14B—C15B—C16B | 0.7 (4) |
| C1A—C2A—C3A—C4A | 44.18 (19) | C14B—C15B—C16B—C17B | 0.1 (4) |
| C2A—C3A—C4A—C18A | −158.98 (17) | C15B—C16B—C17B—C12B | −0.6 (3) |
| C2A—C3A—C4A—C5A | −32.0 (2) | C13B—C12B—C17B—C16B | 0.4 (3) |
| O1A—C1A—C5A—C4A | 132.32 (17) | C2B—C12B—C17B—C16B | −178.11 (19) |
| C6A—C1A—C5A—C4A | −102.40 (19) | C3B—C4B—C18B—C19B | 1.4 (3) |
| C2A—C1A—C5A—C4A | 18.8 (2) | C5B—C4B—C18B—C19B | −121.0 (2) |
| C18A—C4A—C5A—C1A | 134.97 (19) | C3B—C4B—C18B—C23B | −175.52 (17) |
| C3A—C4A—C5A—C1A | 7.5 (2) | C5B—C4B—C18B—C23B | 62.1 (2) |
| O1A—C1A—C6A—C7A | 153.34 (17) | C23B—C18B—C19B—C20B | 0.6 (3) |
| C5A—C1A—C6A—C7A | 27.4 (2) | C4B—C18B—C19B—C20B | −176.4 (2) |
| C2A—C1A—C6A—C7A | −88.4 (2) | C18B—C19B—C20B—C21B | −1.4 (4) |
| O1A—C1A—C6A—C11A | −27.9 (2) | C19B—C20B—C21B—C22B | 0.4 (4) |
| C5A—C1A—C6A—C11A | −153.85 (17) | C20B—C21B—C22B—C23B | 1.3 (4) |
| C2A—C1A—C6A—C11A | 90.3 (2) | C21B—C22B—C23B—O3B | 176.2 (2) |
| C11A—C6A—C7A—C8A | 0.8 (3) | C21B—C22B—C23B—C18B | −2.1 (3) |
| C1A—C6A—C7A—C8A | 179.5 (2) | C19B—C18B—C23B—O3B | −177.27 (18) |
| C6A—C7A—C8A—C9A | 0.9 (4) | C4B—C18B—C23B—O3B | −0.1 (3) |
| C7A—C8A—C9A—C10A | −1.1 (4) | C19B—C18B—C23B—C22B | 1.1 (3) |
| C8A—C9A—C10A—C11A | −0.3 (4) | C4B—C18B—C23B—C22B | 178.27 (19) |
| C9A—C10A—C11A—C6A | 2.0 (3) | C22B—C23B—O3B—C24B | −3.6 (3) |
| C7A—C6A—C11A—C10A | −2.2 (3) | C18B—C23B—O3B—C24B | 174.72 (19) |
| C1A—C6A—C11A—C10A | 179.01 (18) | O1C—C1C—C2C—O2C | 44.87 (18) |
| O2A—C2A—C12A—C13A | 29.2 (2) | C6C—C1C—C2C—O2C | 165.05 (14) |
| C3A—C2A—C12A—C13A | 148.90 (18) | C5C—C1C—C2C—O2C | −72.76 (16) |
| C1A—C2A—C12A—C13A | −91.9 (2) | O1C—C1C—C2C—C3C | 156.57 (14) |
| O2A—C2A—C12A—C17A | −148.79 (17) | C6C—C1C—C2C—C3C | −83.25 (17) |
| C3A—C2A—C12A—C17A | −29.1 (3) | C5C—C1C—C2C—C3C | 38.94 (16) |
| C1A—C2A—C12A—C17A | 90.1 (2) | O1C—C1C—C2C—C12C | −76.92 (18) |
| C17A—C12A—C13A—C14A | 0.7 (3) | C6C—C1C—C2C—C12C | 43.3 (2) |
| C2A—C12A—C13A—C14A | −177.40 (18) | C5C—C1C—C2C—C12C | 165.45 (15) |
| C12A—C13A—C14A—C15A | 0.9 (3) | O2C—C2C—C3C—C4C | 69.39 (17) |
| C13A—C14A—C15A—C16A | −1.7 (3) | C12C—C2C—C3C—C4C | −168.72 (15) |
| C14A—C15A—C16A—C17A | 0.8 (3) | C1C—C2C—C3C—C4C | −41.95 (17) |
| C15A—C16A—C17A—C12A | 0.8 (3) | C2C—C3C—C4C—C18C | 155.40 (15) |
| C13A—C12A—C17A—C16A | −1.6 (3) | C2C—C3C—C4C—C5C | 28.12 (18) |
| C2A—C12A—C17A—C16A | 176.49 (18) | O1C—C1C—C5C—C4C | −134.59 (15) |
| C3A—C4A—C18A—C23A | −168.32 (19) | C6C—C1C—C5C—C4C | 99.72 (17) |
| C5A—C4A—C18A—C23A | 70.4 (3) | C2C—C1C—C5C—C4C | −21.77 (17) |
| C3A—C4A—C18A—C19A | 10.8 (3) | C18C—C4C—C5C—C1C | −130.87 (16) |
| C5A—C4A—C18A—C19A | −110.5 (2) | C3C—C4C—C5C—C1C | −3.16 (18) |
| C23A—C18A—C19A—C20A | −0.1 (3) | O1C—C1C—C6C—C11C | 25.1 (2) |
| C4A—C18A—C19A—C20A | −179.2 (2) | C5C—C1C—C6C—C11C | 151.88 (17) |
| C18A—C19A—C20A—C21A | 1.1 (4) | C2C—C1C—C6C—C11C | −92.3 (2) |
| C19A—C20A—C21A—C22A | −0.3 (4) | O1C—C1C—C6C—C7C | −156.75 (16) |
| C20A—C21A—C22A—C23A | −1.4 (4) | C5C—C1C—C6C—C7C | −30.0 (2) |
| C21A—C22A—C23A—O3A | −178.4 (2) | C2C—C1C—C6C—C7C | 85.8 (2) |
| C21A—C22A—C23A—C18A | 2.5 (3) | C11C—C6C—C7C—C8C | 0.9 (3) |
| C19A—C18A—C23A—O3A | 179.10 (19) | C1C—C6C—C7C—C8C | −177.29 (16) |
| C4A—C18A—C23A—O3A | −1.7 (3) | C6C—C7C—C8C—C9C | 0.1 (3) |
| C19A—C18A—C23A—C22A | −1.7 (3) | C7C—C8C—C9C—C10C | −0.8 (3) |
| C4A—C18A—C23A—C22A | 177.4 (2) | C8C—C9C—C10C—C11C | 0.6 (3) |
| C22A—C23A—O3A—C24A | 8.7 (3) | C9C—C10C—C11C—C6C | 0.4 (3) |
| C18A—C23A—O3A—C24A | −172.2 (2) | C7C—C6C—C11C—C10C | −1.1 (3) |
| O1B—C1B—C2B—O2B | −46.09 (18) | C1C—C6C—C11C—C10C | 177.08 (18) |
| C6B—C1B—C2B—O2B | −164.67 (15) | O2C—C2C—C12C—C17C | −18.7 (2) |
| C5B—C1B—C2B—O2B | 72.53 (16) | C3C—C2C—C12C—C17C | −139.00 (18) |
| O1B—C1B—C2B—C12B | 75.0 (2) | C1C—C2C—C12C—C17C | 101.2 (2) |
| C6B—C1B—C2B—C12B | −43.6 (2) | O2C—C2C—C12C—C13C | 160.22 (17) |
| C5B—C1B—C2B—C12B | −166.40 (15) | C3C—C2C—C12C—C13C | 39.9 (2) |
| O1B—C1B—C2B—C3B | −159.84 (14) | C1C—C2C—C12C—C13C | −79.8 (2) |
| C6B—C1B—C2B—C3B | 81.58 (18) | C17C—C12C—C13C—C14C | 0.5 (3) |
| C5B—C1B—C2B—C3B | −41.22 (16) | C2C—C12C—C13C—C14C | −178.47 (19) |
| O2B—C2B—C3B—C4B | −63.58 (18) | C12C—C13C—C14C—C15C | 0.0 (3) |
| C12B—C2B—C3B—C4B | 170.51 (15) | C13C—C14C—C15C—C16C | −0.4 (3) |
| C1B—C2B—C3B—C4B | 43.51 (17) | C14C—C15C—C16C—C17C | 0.3 (3) |
| C2B—C3B—C4B—C18B | −156.71 (15) | C15C—C16C—C17C—C12C | 0.2 (3) |
| C2B—C3B—C4B—C5B | −28.22 (18) | C13C—C12C—C17C—C16C | −0.6 (3) |
| O1B—C1B—C5B—C4B | 141.76 (15) | C2C—C12C—C17C—C16C | 178.34 (19) |
| C6B—C1B—C5B—C4B | −97.88 (18) | C3C—C4C—C18C—C19C | 0.2 (3) |
| C2B—C1B—C5B—C4B | 24.37 (18) | C5C—C4C—C18C—C19C | 122.14 (19) |
| C18B—C4B—C5B—C1B | 129.23 (17) | C3C—C4C—C18C—C23C | 176.88 (17) |
| C3B—C4B—C5B—C1B | 1.50 (19) | C5C—C4C—C18C—C23C | −61.2 (2) |
| O1B—C1B—C6B—C11B | −34.6 (2) | C23C—C18C—C19C—C20C | 0.5 (3) |
| C5B—C1B—C6B—C11B | −158.06 (17) | C4C—C18C—C19C—C20C | 177.27 (18) |
| C2B—C1B—C6B—C11B | 86.1 (2) | C18C—C19C—C20C—C21C | 0.5 (3) |
| O1B—C1B—C6B—C7B | 147.27 (17) | C19C—C20C—C21C—C22C | −0.6 (3) |
| C5B—C1B—C6B—C7B | 23.8 (2) | C20C—C21C—C22C—C23C | −0.4 (3) |
| C2B—C1B—C6B—C7B | −92.0 (2) | C21C—C22C—C23C—O3C | −177.47 (19) |
| C11B—C6B—C7B—C8B | 0.0 (3) | C21C—C22C—C23C—C18C | 1.5 (3) |
| C1B—C6B—C7B—C8B | 178.12 (18) | C19C—C18C—C23C—O3C | 177.48 (17) |
| C6B—C7B—C8B—C9B | −0.1 (3) | C4C—C18C—C23C—O3C | 0.6 (3) |
| C7B—C8B—C9B—C10B | −0.1 (3) | C19C—C18C—C23C—C22C | −1.6 (3) |
| C8B—C9B—C10B—C11B | 0.5 (4) | C4C—C18C—C23C—C22C | −178.46 (17) |
| C9B—C10B—C11B—C6B | −0.6 (3) | C22C—C23C—O3C—C24C | −5.8 (3) |
| C7B—C6B—C11B—C10B | 0.4 (3) | C18C—C23C—O3C—C24C | 175.19 (18) |
(1R,2S,4r)-4-(2-Methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol (II) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1A—H1A···O2Ci | 0.85 (3) | 2.08 (3) | 2.8931 (19) | 160 (3) |
| O2A—H2A···O1A | 0.88 (3) | 2.04 (3) | 2.605 (2) | 121 (2) |
| O1B—H1B···O2B | 0.90 (3) | 2.05 (3) | 2.590 (2) | 117 (2) |
| O2B—H2B···O2A | 0.83 (2) | 1.98 (2) | 2.802 (2) | 170 (2) |
| O1C—H1C···O1B | 0.88 (3) | 1.96 (3) | 2.833 (2) | 171 (2) |
| O2C—H2C···O1C | 0.85 (3) | 2.00 (3) | 2.587 (2) | 125 (2) |
Symmetry code: (i) x−1, y−1, z.
Funding Statement
This work was funded by the State Program of TIPS RAS grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, II, New_Global_Publ_Block. DOI: 10.1107/S2056989019008673/fy2139sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019008673/fy2139Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989019008673/fy2139IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989019008673/fy2139Isup4.cml
Supporting information file. DOI: 10.1107/S2056989019008673/fy2139IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report