Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111008419/ov3002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111008419/ov3002Isup2.hkl |
CCDC reference: 824042
For related literature, see: Bakar Bin Baba, Gold & Hibbert (1985); Beccalli et al. (2007); Burr & Strong (1959); Derk et al. (2008); Desiraju (1995); Droste et al. (1969); Hartwig (2008); Hooft et al. (2008); Ohkura et al. (2004); Spek (2009); Yu et al. (2009).
The synthesis of (I) and 1,1,2,2-tetraphenylethane-1,2-diol from dioxane and benzophenone has been described in the literature (Droste et al., 1969). Irradition of a dioxane solution containing benzophenone for 20 h with a mercury arc lamp (340 nm) and a nickel sulfate aqueous filter produces (I) and 1,1,2,2-tetraphenylethane-1,2-diol as the major products. We have prepared (I) by an alternate method using microwave irradiation by the following procedure. Benzophenone (0.55 mmol) was placed in a 125 ml Erlenmeyer flask containing Zn dust (1.02 mmol), ammonium formate (3.96 mmol) and dioxane (5 ml). The reactants were irradiated in a domestic microwave oven (70% power, 1.05 kW) with a heat sink for three periods of 5 min, yielding an amber-colored solution. Excess dioxane was added, the Zn dust was removed by filtration and the filtrate was concentrated by rotoevaporation. Removal of the solvent yielded an amber-colored oil and white crystals. The white solid was the major product. It was easily removed by filtration with a cold methanol wash and was determined to be 1,1,2,2-tetraphenylethane-1,2-diol (m.p. 443–444 K). The remaining amber-colored oil was determined to be a mixture of (I) and several unknown by-products. The oil was purified by chromatography using a 5:2:1 solution of ethyl acetate–toluene–methanol on silica gel. Compound (I) was crystallized by slow diffusion of toluene, yielding colorless crystals [m.p. 387 K (literature value? 388 K)]. The 1H NMR (CDCl3) spectrum corresponds to that reported in the literature. MALDI–TOF MS: [M+H]+ 271 m/z.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C17H18O3 | F(000) = 576 |
Mr = 270.31 | Dx = 1.289 Mg m−3 |
Monoclinic, Cc | Melting point: 387 K |
Hall symbol: C -2yc | Cu Kα radiation, λ = 1.5418 Å |
a = 12.9108 (8) Å | Cell parameters from 2419 reflections |
b = 10.5408 (5) Å | θ = 4.3–72.5° |
c = 10.3022 (7) Å | µ = 0.70 mm−1 |
β = 94.016 (6)° | T = 100 K |
V = 1398.59 (14) Å3 | Needle, colourless |
Z = 4 | 0.37 × 0.11 × 0.04 mm |
Oxford GEMINI CCD area-detector diffractometer | 2064 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 10.2836 pixels mm-1 | θmax = 72.6°, θmin = 5.4° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −12→12 |
Tmin = 0.915, Tmax = 0.988 | l = −9→12 |
4014 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | All H-atom parameters refined |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0319P)2 + 0.393P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2064 reflections | Δρmax = 0.18 e Å−3 |
251 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Absolute structure: Hooft et al. (2008), with 723 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (2) |
C17H18O3 | V = 1398.59 (14) Å3 |
Mr = 270.31 | Z = 4 |
Monoclinic, Cc | Cu Kα radiation |
a = 12.9108 (8) Å | µ = 0.70 mm−1 |
b = 10.5408 (5) Å | T = 100 K |
c = 10.3022 (7) Å | 0.37 × 0.11 × 0.04 mm |
β = 94.016 (6)° |
Oxford GEMINI CCD area-detector diffractometer | 2064 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 1805 reflections with I > 2σ(I) |
Tmin = 0.915, Tmax = 0.988 | Rint = 0.015 |
4014 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | All H-atom parameters refined |
wR(F2) = 0.070 | Δρmax = 0.18 e Å−3 |
S = 1.04 | Δρmin = −0.14 e Å−3 |
2064 reflections | Absolute structure: Hooft et al. (2008), with 723 Friedel pairs |
251 parameters | Absolute structure parameter: −0.2 (2) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
C1 | 0.23251 (16) | 0.34864 (19) | 0.5551 (2) | 0.0331 (5) | |
C2 | 0.19656 (17) | 0.4739 (2) | 0.6158 (2) | 0.0352 (5) | |
C3 | 0.10390 (18) | 0.4619 (2) | 0.6951 (3) | 0.0411 (6) | |
C4 | 0.05609 (19) | 0.6716 (2) | 0.6418 (2) | 0.0458 (6) | |
C5 | 0.14556 (19) | 0.6817 (2) | 0.5585 (2) | 0.0425 (6) | |
C6 | 0.32704 (16) | 0.37083 (18) | 0.47492 (19) | 0.0330 (5) | |
C7 | 0.3398 (2) | 0.2943 (2) | 0.3677 (2) | 0.0470 (6) | |
C8 | 0.4247 (2) | 0.3069 (3) | 0.2967 (3) | 0.0606 (8) | |
C9 | 0.4989 (2) | 0.3948 (3) | 0.3284 (3) | 0.0620 (8) | |
H9 | 0.563 (3) | 0.412 (3) | 0.294 (3) | 0.074* | |
C10 | 0.4885 (2) | 0.4736 (3) | 0.4339 (3) | 0.0558 (7) | |
C11 | 0.40233 (18) | 0.4602 (2) | 0.5077 (2) | 0.0412 (5) | |
C12 | 0.26435 (16) | 0.25065 (19) | 0.6600 (2) | 0.0344 (5) | |
C13 | 0.24572 (19) | 0.1232 (2) | 0.6353 (3) | 0.0437 (6) | |
C16 | 0.3528 (2) | 0.1919 (3) | 0.8644 (3) | 0.0533 (7) | |
O1 | 0.17561 (11) | 0.56064 (12) | 0.51221 (14) | 0.0385 (4) | |
O2 | 0.07728 (12) | 0.58393 (16) | 0.74518 (16) | 0.0511 (4) | |
O3 | 0.14795 (12) | 0.29540 (15) | 0.47828 (17) | 0.0456 (4) | |
C17 | 0.31819 (19) | 0.2836 (2) | 0.7755 (2) | 0.0452 (6) | |
C14 | 0.2808 (2) | 0.0320 (2) | 0.7246 (3) | 0.0571 (8) | |
C15 | 0.3340 (2) | 0.0663 (2) | 0.8392 (3) | 0.0551 (7) | |
H15 | 0.364 (2) | 0.010 (3) | 0.899 (3) | 0.066* | |
H2 | 0.2586 (17) | 0.514 (2) | 0.678 (2) | 0.036 (6)* | |
H3A | 0.1217 (18) | 0.412 (2) | 0.772 (2) | 0.048 (7)* | |
H3B | 0.0436 (19) | 0.431 (2) | 0.645 (3) | 0.053 (8)* | |
H4A | −0.003 (2) | 0.643 (2) | 0.592 (3) | 0.055 (7)* | |
H4B | 0.0393 (18) | 0.758 (3) | 0.684 (2) | 0.052 (7)* | |
H5A | 0.212 (2) | 0.721 (2) | 0.615 (3) | 0.063 (8)* | |
H5B | 0.1348 (18) | 0.741 (2) | 0.484 (3) | 0.051 (7)* | |
H7 | 0.291 (2) | 0.221 (3) | 0.348 (3) | 0.066 (8)* | |
H8 | 0.433 (3) | 0.251 (4) | 0.222 (4) | 0.094 (11)* | |
H10 | 0.529 (2) | 0.535 (2) | 0.460 (2) | 0.044 (7)* | |
H11 | 0.3979 (19) | 0.509 (2) | 0.584 (3) | 0.054 (7)* | |
H13 | 0.213 (2) | 0.103 (3) | 0.561 (3) | 0.057 (9)* | |
H14 | 0.265 (2) | −0.055 (3) | 0.709 (3) | 0.078 (10)* | |
H16 | 0.390 (2) | 0.216 (3) | 0.936 (3) | 0.057 (8)* | |
H17 | 0.329 (2) | 0.364 (2) | 0.796 (2) | 0.052 (7)* | |
H30A | 0.1324 (19) | 0.348 (2) | 0.417 (3) | 0.049 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0370 (11) | 0.0264 (10) | 0.0342 (12) | 0.0021 (8) | −0.0102 (9) | 0.0010 (9) |
C2 | 0.0382 (11) | 0.0285 (10) | 0.0384 (13) | 0.0062 (9) | −0.0011 (10) | 0.0038 (9) |
C3 | 0.0401 (13) | 0.0417 (13) | 0.0407 (14) | −0.0001 (10) | −0.0040 (11) | 0.0033 (11) |
C4 | 0.0455 (14) | 0.0489 (14) | 0.0419 (15) | 0.0204 (11) | −0.0051 (11) | −0.0012 (12) |
C5 | 0.0565 (15) | 0.0319 (11) | 0.0382 (14) | 0.0156 (10) | −0.0024 (12) | 0.0016 (10) |
C6 | 0.0442 (12) | 0.0268 (9) | 0.0271 (11) | 0.0107 (8) | −0.0050 (9) | 0.0036 (8) |
C7 | 0.0675 (16) | 0.0359 (11) | 0.0372 (14) | 0.0151 (11) | 0.0002 (12) | −0.0029 (11) |
C8 | 0.082 (2) | 0.0605 (16) | 0.0396 (16) | 0.0302 (16) | 0.0051 (15) | 0.0000 (14) |
C9 | 0.0584 (16) | 0.086 (2) | 0.0437 (17) | 0.0376 (16) | 0.0174 (13) | 0.0275 (16) |
C10 | 0.0425 (14) | 0.0622 (17) | 0.0620 (19) | 0.0020 (12) | −0.0024 (13) | 0.0162 (15) |
C11 | 0.0415 (12) | 0.0431 (12) | 0.0386 (14) | 0.0038 (10) | −0.0006 (11) | −0.0019 (12) |
C12 | 0.0388 (11) | 0.0291 (10) | 0.0353 (12) | 0.0026 (8) | 0.0019 (9) | 0.0028 (9) |
C13 | 0.0500 (13) | 0.0301 (10) | 0.0498 (16) | −0.0049 (10) | −0.0057 (12) | 0.0062 (11) |
C16 | 0.0667 (16) | 0.0538 (14) | 0.0378 (15) | 0.0118 (13) | −0.0083 (13) | 0.0016 (12) |
O1 | 0.0506 (9) | 0.0300 (7) | 0.0342 (8) | 0.0103 (6) | −0.0014 (7) | 0.0033 (7) |
O2 | 0.0542 (10) | 0.0538 (10) | 0.0453 (10) | 0.0203 (8) | 0.0036 (8) | 0.0019 (8) |
O3 | 0.0512 (9) | 0.0343 (8) | 0.0482 (10) | −0.0073 (7) | −0.0185 (8) | 0.0039 (8) |
C17 | 0.0591 (15) | 0.0334 (11) | 0.0413 (14) | 0.0077 (10) | −0.0094 (11) | −0.0014 (11) |
C14 | 0.0677 (16) | 0.0326 (12) | 0.070 (2) | −0.0022 (11) | −0.0039 (15) | 0.0161 (12) |
C15 | 0.0660 (17) | 0.0466 (14) | 0.0523 (17) | 0.0117 (12) | 0.0027 (13) | 0.0214 (13) |
C1—O3 | 1.418 (2) | C7—H7 | 1.01 (3) |
C1—C12 | 1.530 (3) | C8—C9 | 1.356 (5) |
C1—C6 | 1.539 (3) | C8—H8 | 0.98 (4) |
C1—C2 | 1.546 (3) | C9—C10 | 1.381 (4) |
C2—O1 | 1.417 (2) | C9—H9 | 0.94 (3) |
C2—C3 | 1.500 (3) | C10—C11 | 1.398 (4) |
C2—H2 | 1.07 (2) | C10—H10 | 0.86 (2) |
C3—O2 | 1.437 (3) | C11—H11 | 0.94 (3) |
C3—H3A | 0.96 (3) | C12—C17 | 1.380 (3) |
C3—H3B | 0.96 (3) | C12—C13 | 1.386 (3) |
C4—O2 | 1.422 (3) | C13—C14 | 1.385 (4) |
C4—C5 | 1.490 (3) | C13—H13 | 0.87 (3) |
C4—H4A | 0.94 (3) | C16—C15 | 1.368 (4) |
C4—H4B | 1.04 (3) | C16—C17 | 1.385 (3) |
C5—O1 | 1.426 (2) | C16—H16 | 0.89 (3) |
C5—H5A | 1.08 (3) | O3—H30A | 0.85 (3) |
C5—H5B | 0.99 (3) | C17—H17 | 0.88 (2) |
C6—C11 | 1.379 (3) | C14—C15 | 1.372 (4) |
C6—C7 | 1.388 (3) | C14—H14 | 0.96 (3) |
C7—C8 | 1.366 (4) | C15—H15 | 0.92 (3) |
O3—C1—C12 | 106.56 (16) | C6—C7—H7 | 119.9 (16) |
O3—C1—C6 | 111.66 (17) | C9—C8—C7 | 121.2 (3) |
C12—C1—C6 | 107.32 (16) | C9—C8—H8 | 119 (2) |
O3—C1—C2 | 108.80 (17) | C7—C8—H8 | 120 (2) |
C12—C1—C2 | 111.38 (18) | C8—C9—C10 | 119.7 (3) |
C6—C1—C2 | 111.05 (16) | C8—C9—H9 | 131.9 (18) |
O1—C2—C3 | 110.31 (17) | C10—C9—H9 | 108.3 (19) |
O1—C2—C1 | 107.07 (17) | C9—C10—C11 | 119.4 (3) |
C3—C2—C1 | 114.93 (18) | C9—C10—H10 | 127.4 (18) |
O1—C2—H2 | 106.8 (12) | C11—C10—H10 | 113.1 (18) |
C3—C2—H2 | 107.4 (12) | C6—C11—C10 | 120.7 (2) |
C1—C2—H2 | 110.1 (11) | C6—C11—H11 | 119.6 (15) |
O2—C3—C2 | 109.88 (18) | C10—C11—H11 | 119.6 (16) |
O2—C3—H3A | 104.1 (14) | C17—C12—C13 | 118.2 (2) |
C2—C3—H3A | 109.8 (14) | C17—C12—C1 | 122.22 (18) |
O2—C3—H3B | 107.1 (15) | C13—C12—C1 | 119.4 (2) |
C2—C3—H3B | 112.3 (16) | C14—C13—C12 | 120.5 (2) |
H3A—C3—H3B | 113 (2) | C14—C13—H13 | 122.2 (18) |
O2—C4—C5 | 111.21 (18) | C12—C13—H13 | 117.3 (18) |
O2—C4—H4A | 107.9 (16) | C15—C16—C17 | 120.3 (3) |
C5—C4—H4A | 109.8 (16) | C15—C16—H16 | 121.1 (18) |
O2—C4—H4B | 106.8 (14) | C17—C16—H16 | 118.5 (19) |
C5—C4—H4B | 111.9 (14) | C2—O1—C5 | 111.58 (16) |
H4A—C4—H4B | 109 (2) | C4—O2—C3 | 110.54 (19) |
O1—C5—C4 | 111.60 (19) | C1—O3—H30A | 106.5 (16) |
O1—C5—H5A | 107.4 (14) | C12—C17—C16 | 121.0 (2) |
C4—C5—H5A | 109.7 (15) | C12—C17—H17 | 121.0 (17) |
O1—C5—H5B | 109.4 (15) | C16—C17—H17 | 118.0 (17) |
C4—C5—H5B | 114.8 (14) | C15—C14—C13 | 120.6 (2) |
H5A—C5—H5B | 103.5 (19) | C15—C14—H14 | 119.3 (18) |
C11—C6—C7 | 118.1 (2) | C13—C14—H14 | 120.0 (18) |
C11—C6—C1 | 122.98 (19) | C16—C15—C14 | 119.4 (3) |
C7—C6—C1 | 118.8 (2) | C16—C15—H15 | 116.0 (17) |
C8—C7—C6 | 120.9 (3) | C14—C15—H15 | 124.4 (17) |
C8—C7—H7 | 118.8 (15) | ||
O3—C1—C2—O1 | −66.7 (2) | C1—C6—C11—C10 | 177.8 (2) |
C12—C1—C2—O1 | 176.16 (16) | C9—C10—C11—C6 | −1.1 (4) |
C6—C1—C2—O1 | 56.6 (2) | O3—C1—C12—C17 | −157.7 (2) |
O3—C1—C2—C3 | 56.2 (2) | C6—C1—C12—C17 | 82.6 (2) |
C12—C1—C2—C3 | −61.0 (2) | C2—C1—C12—C17 | −39.2 (3) |
C6—C1—C2—C3 | 179.50 (18) | O3—C1—C12—C13 | 27.2 (3) |
O1—C2—C3—O2 | −58.3 (2) | C6—C1—C12—C13 | −92.5 (2) |
C1—C2—C3—O2 | −179.48 (18) | C2—C1—C12—C13 | 145.7 (2) |
O2—C4—C5—O1 | 54.2 (3) | C17—C12—C13—C14 | −0.2 (4) |
O3—C1—C6—C11 | 155.27 (19) | C1—C12—C13—C14 | 175.1 (2) |
C12—C1—C6—C11 | −88.3 (2) | C3—C2—O1—C5 | 56.6 (2) |
C2—C1—C6—C11 | 33.6 (3) | C1—C2—O1—C5 | −177.70 (17) |
O3—C1—C6—C7 | −27.5 (2) | C4—C5—O1—C2 | −54.6 (2) |
C12—C1—C6—C7 | 89.0 (2) | C5—C4—O2—C3 | −56.3 (3) |
C2—C1—C6—C7 | −149.1 (2) | C2—C3—O2—C4 | 58.3 (2) |
C11—C6—C7—C8 | 0.1 (3) | C13—C12—C17—C16 | 0.0 (4) |
C1—C6—C7—C8 | −177.3 (2) | C1—C12—C17—C16 | −175.1 (2) |
C6—C7—C8—C9 | −0.2 (4) | C15—C16—C17—C12 | 0.0 (4) |
C7—C8—C9—C10 | −0.3 (4) | C12—C13—C14—C15 | 0.3 (4) |
C8—C9—C10—C11 | 1.0 (4) | C17—C16—C15—C14 | 0.2 (4) |
C7—C6—C11—C10 | 0.5 (3) | C13—C14—C15—C16 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H30A···O2i | 0.86 (3) | 1.99 (3) | 2.813 (2) | 160 (2) |
Symmetry code: (i) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H18O3 |
Mr | 270.31 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 100 |
a, b, c (Å) | 12.9108 (8), 10.5408 (5), 10.3022 (7) |
β (°) | 94.016 (6) |
V (Å3) | 1398.59 (14) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.37 × 0.11 × 0.04 |
Data collection | |
Diffractometer | Oxford GEMINI CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.915, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4014, 2064, 1805 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.070, 1.04 |
No. of reflections | 2064 |
No. of parameters | 251 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.18, −0.14 |
Absolute structure | Hooft et al. (2008), with 723 Friedel pairs |
Absolute structure parameter | −0.2 (2) |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C1—O3 | 1.418 (2) | C1—C2 | 1.546 (3) |
C1—C12 | 1.530 (3) | C2—O1 | 1.417 (2) |
C1—C6 | 1.539 (3) | C2—C3 | 1.500 (3) |
O3—C1—C12 | 106.56 (16) | O1—C2—C3 | 110.31 (17) |
O3—C1—C6 | 111.66 (17) | O1—C2—C1 | 107.07 (17) |
C12—C1—C6 | 107.32 (16) | C3—C2—C1 | 114.93 (18) |
O3—C1—C2 | 108.80 (17) | O1—C2—H2 | 106.8 (12) |
C12—C1—C2 | 111.38 (18) | C3—C2—H2 | 107.4 (12) |
C6—C1—C2 | 111.05 (16) | C1—C2—H2 | 110.1 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H30A···O2i | 0.86 (3) | 1.99 (3) | 2.813 (2) | 160 (2) |
Symmetry code: (i) x, −y+1, z−1/2. |
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The formation of C—C bonds is an important synthetic step in organic synthesis, and there are several well known methods that efficiently promote this bond-formation process. One frequently used method involves the coupling of carbon radicals generated during photolysis (Ohkura et al., 2004; Derk et al., 2008), radiolysis (Burr & Strong, 1959), oxidation reactions (Beccalli et al., 2007; Yu et al., 2009) and organometallic catalysed reactions (Hartwig, 2008). The known title compound, (I), was synthesized using microwave irradiation to promote C—C bond coupling between dioxane and benzophenone, and isolated as a racemic mixture upon crystallization. The synthesis of (I) has been reported previously (Bakar Bin Baba et al., 1985; Droste et al., 1969) by UV irradiation of benzophenone in dioxane, and characterized by 1H and 13C NMR and mass spectrometry. However, to date, no crystal structure of (I) has been reported.
The C—C bond coupling between the 2-position C atom of dioxane and the carbonyl C atom of benzophenone results in the formation of a stereocenter at atom C2. Compound (I) crystallizes with one molecule in the asymmetric unit in the noncentrosymmetric space group Cc, which was confirmed using the program PLATON (routines ADDSYM and NEWSYM; Spek, 2009). Two enantiomeric forms are present and the structure of the S form is shown in Fig. 1. The Hooft analysis parameters P2(true) = 1.000, P3(true) = 1.000, P3(false) = 0.000 and Hooft y = 0.139 (069) obtained from PLATON were used to assign the absolute structure (Hooft et al., 2008).
The C—C and C—O bond distances and associated bond angles around atoms C1 [average = 109.04 (17)°] and C2 [average = 109.48 (14)°] are consistent with sp3 hybridization. The C—C and C—O distances, and respective angles, for the phenyl and dioxanyl groups are normal. The phenyl rings adopt a twisted arrangement, minimizing ring-to-ring and H···H atom interactions, while the dioxanyl group adopts a distorted-chair conformation.
Compound (I) displays intermolecular O—H···O' hydrogen bonding between dioxanyl and hydroxy groups (Desiraju, 1995). A view of the interlinked one-dimensional hydrogen-bonded chain of molecules of (I), projected along the crystallographic c axis, is shown in Fig. 2, illustrating the strong hydrogen-bonding interaction. The O3···O2i distance is 2.812 (2) Å and the O3—H30A···O2i angle is 160 (2)° between symmetry-related molecules [symmetry code: (i) x, -y + 1, z - 1/2].