Racemic (1,4-dioxan-2-yl)diphenyl­methanol

Hsiao, T.; Buchanan, R.M.; Mashuta, M.S.

doi:10.1107/S0108270111008419

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 67| Part 4| April 2011| Pages o129-o130

doi:10.1107/S0108270111008419

Racemic (1,4-dioxan-2-yl)diphenylmethanol

Tomi Hsiao,^a Robert M. Buchanan ^a and Mark S. Mashuta ^a ^*

^aDepartment of Chemistry, University of Louisville, Louisville, KY 40292, USA
^*Correspondence e-mail: msmashuta.xray@louisville.edu

(Received 11 February 2011; accepted 5 March 2011; online 11 March 2011)

The title compound, C₁₇H₁₈O₃, prepared by microwave irradiation of benzophenone and dioxane, crystallizes in a racemic mixture that forms one-dimensional chains via strong hydrogen bonding of the hydroxy group to the adjacent symmetry-generated 1,4-dioxan-2-yl group; the O—H⋯O distance is 1.99 (3) Å and the O—H⋯O angle is 160 (2)°.

Comment

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 was isolated as a racemic mixture upon crystallization. (I) has been prepared previously by UV irradiation of benzophenone in dioxane, and characterized by ¹H and ¹³C NMR and mass spectrometry (Bakar Bin Baba et al., 1985 ; Droste et al., 1969 ). 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 = 0.14 (7) obtained from PLATON were used to assign the absolute configuration (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 (Table 1). 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, with dimensions as listed in Table 2.

Figure 1
A view of the S enantiomer of (I)

, showing 50% probability displacement ellipsoids.

Figure 2
A packing diagram for (I)

, showing the intermolecular hydrogen-bonding interactions between atoms H30A and O2ⁱ of adjacent S and R enantiomers. [Symmetry code: (i) x, −y + 1, z − $[{1\over 2}]$ .]

Experimental

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 alternative 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 amber-colored oil was determined to be a mixture of (I) and several unknown by-products. It 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 (Bakar Bin Baba et al., 1985)]. The ¹H NMR (CDCl₃) spectrum corresponds to that reported in the literature. MALDI–TOF MS: [M + H]⁺ 271 m/z.

Crystal data

C₁₇H₁₈O₃
M_r = 270.31
Monoclinic, C c
a = 12.9108 (8) Å
b = 10.5408 (5) Å
c = 10.3022 (7) Å
β = 94.016 (6)°
V = 1398.59 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.37 × 0.11 × 0.04 mm

Data collection

Oxford GEMINI CCD area-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Version 1.171.34.36. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.915, T_max = 0.988
4014 measured reflections
2064 independent reflections
1805 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.070
S = 1.04
2064 reflections
251 parameters
All H-atom parameters refined
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Hooft et al. (2008), with 723 Friedel pairs
Flack parameter: −0.2 (2)

Table 1
Selected geometric parameters (Å, °)

C1—O3	1.418 (2)
C1—C12	1.530 (3)
C1—C6	1.539 (3)
C1—C2	1.546 (3)
C2—O1	1.417 (2)
C2—C3	1.500 (3)

O3—C1—C12	106.56 (16)
O3—C1—C6	111.66 (17)
C12—C1—C6	107.32 (16)
O3—C1—C2	108.80 (17)
C12—C1—C2	111.38 (18)
C6—C1—C2	111.05 (16)
O1—C2—C3	110.31 (17)
O1—C2—C1	107.07 (17)
C3—C2—C1	114.93 (18)
O1—C2—H2	106.8 (12)
C3—C2—H2	107.4 (12)
C1—C2—H2	110.1 (11)

Table 2
Hydrogen-bond geometry (Å, °)

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) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Version 1.171.33.34d. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Version 1.171.34.36. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); data reduction: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Version 1.171.34.36. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S0108270111008419/ov3002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270111008419/ov3002Isup2.hkl

Comment top

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].

Related literature top

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).

Experimental top

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.

Computing details top

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).

Figures top

	Fig. 1. A view of the S enantiomer of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. A packing diagram for (I), showing the intermolecular hydrogen-bonding interactions between atoms H30A and O2ⁱ of adjacent S and R enantiomers. [Symmetry code: (i) x, -y + 1, z - 1/2.]

(1,4-Dioxan-2-yl)diphenylmethanol top

Crystal data top

C₁₇H₁₈O₃	F(000) = 576
M_r = 270.31	D_x = 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

Data collection top

Oxford GEMINI CCD area-detector diffractometer	2064 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1805 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 10.2836 pixels mm^-1	θ_max = 72.6°, θ_min = 5.4°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.915, T_max = 0.988	l = −9→12
4014 measured reflections

Refinement top

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(F_o²) + (0.0319P)² + 0.393P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2064 reflections	Δρ_max = 0.18 e Å⁻³
251 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₈O₃	V = 1398.59 (14) Å³
M_r = 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)°

Data collection top

Oxford GEMINI CCD area-detector diffractometer	2064 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1805 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.988	R_int = 0.015
4014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	All H-atom parameters refined
wR(F²) = 0.070	Δρ_max = 0.18 e Å⁻³
S = 1.04	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.915, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	4014, 2064, 1805
R_int	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
Δρ_max, Δρ_min (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).

Selected geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

MSM thanks the Department of Energy (grant No. DEFG02-08CH11538), and the Kentucky Research Challenge Trust Fund for upgrade of our X-ray facilities. RMB thanks the Kentucky Science and Engineering Foundation (grant No. KSEF-275-RDE-003) for financial support of this research.

References

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ISSN: 2053-2296

Volume 67| Part 4| April 2011| Pages o129-o130

doi:10.1107/S0108270111008419

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Racemic (1,4-dioxan-2-yl)di­phenyl­methanol

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Racemic (1,4-dioxan-2-yl)diphenylmethanol