7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one

Li, J.; Ma, J.Q.; Mo, W.M.; Shen, Z.L.

doi:10.1107/S1600536814009040

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o665

doi:10.1107/S1600536814009040

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7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one

Jian Li,^a Jia Qi Ma,^a Wei Min Mo ^a and Zhen Lu Shen ^a ^*

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: szlzgd@sina.com

(Received 28 February 2014; accepted 22 April 2014; online 17 May 2014)

In the title compound, C₁₈H₂₂O₄, the cyclohexane and cyclohexanone rings adopt normal chair and half-chair conformations, respectively. The dioxolane ring is almost planar, with an r.m.s. deviation of 0.094 (3) Å. In the crystal, molecules are connected by O—H⋯O hydrogen bonds, forming 2₁ helical chains along the a-axis direction. The chains are further connected by C—H⋯O hydrogen bonds.

CCDC reference: 998726

Related literature

For related structures having condensed cyclohexanone rings, see: Li et al. (2002 ); Lopez-Alvarado et al. (2002 ). For a related structure with a cyclohexanone ring, see: Shallard-Brown et al. (2005 ). For the synthesis, see: Tomizawa et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₂O₄
M_r = 302.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1465 (3) Å
b = 10.0346 (4) Å
c = 16.6469 (6) Å
V = 1527.88 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.29 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.951, T_max = 0.962
12383 measured reflections
1734 independent reflections
1560 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.03
1734 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3ⁱ	0.86 (4)	2.03 (4)	2.857 (3)	163 (3)
C16—H16⋯O3ⁱⁱ	0.93	2.59	3.473 (4)	159
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 998726

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814009040/is5345sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009040/is5345Isup2.hkl

checkCIF report

Comment top

2-(Hydroxyphenylmethyl)-7,7-ethylenedioxybicyclo[3.3.1]nonan-3-one is a key intermediate of the known asymmetrical catalysis of adamantane derivatives that is used in kinetic resolution of secondary alcohols (Tomizawa et al., 2009). Recently. it was synthesized in our lab and the structure was determined.

In the compound (Fig. 1), the C1/C4 cyclohexyl ring adopts a normal chair conformation. The O1/O2 dioxolane ring is almost planar, with a maximum deviation 0.086 (4) Å at the O2 atom. Atoms C3, C7, C8, C9, C5 and O3 are arranged roughly on a plane, with the maximum deviation 0.171 (4) Å at C7 atom. Therefore, the C4/C8 cyclohexanone ring adopts a half-chair conformation, which is different from most known condensed cyclohexanone ring that is part of the complex structure (Lopez-Alvarado et al., 2002; Li et al., 2002), and from free cyclohexanone in solid state (Shallard-Brown et al., 2005).

In the crystal, molecules are linked by O4—H4···O3ⁱ hydrogen bonds (Fig. 2 and Table 1) to form chiral chains. In addition, C—H···O hydrogen bonds help the stability of the crystal. No π–π packing and C—H···π contacts are observed.

Related literature top

For related structures having condensed cyclohexanone rings, see: Li et al. (2002); Lopez-Alvarado et al. (2002). For a related structure with a cyclohexanone ring, see: Shallard-Brown et al. (2005). For the synthesis, see: Tomizawa et al. (2009).

Experimental top

2-(Hydroxyphenylmethyl)-7,7-ethylenedioxybicyclo[3.3.1]nonan-3-one was synthesized through a known procedure (Tomizawa et al., 2009) and obtained as a white solid in a yield of 61% and a purity of 96%. Single crystals were obtained by recrystalization from anhydrous ethanol. MS (ESI) 325.1 (M+Na+) m/z.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels, showing 40% probability displacement ellipsoids.
	Fig. 2. The packing diagram of the title compound viewed down along the a axis. O—H···O hydrogen bonds are shown by thin dashed lines.

7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one top

Crystal data top

C₁₈H₂₂O₄	D_x = 1.314 Mg m⁻³
M_r = 302.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1165 reflections
a = 9.1465 (3) Å	θ = 2.4–24.4°
b = 10.0346 (4) Å	µ = 0.09 mm⁻¹
c = 16.6469 (6) Å	T = 293 K
V = 1527.88 (10) Å³	Prism, colorless
Z = 4	0.35 × 0.30 × 0.29 mm
F(000) = 648

Data collection top

Bruker SMART CCD area detector diffractometer	1734 independent reflections
Radiation source: fine-focus sealed tube	1560 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.0°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.951, T_max = 0.962	k = −12→12
12383 measured reflections	l = −20→20

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0446P)² + 0.4409P] where P = (F_o² + 2F_c²)/3
1734 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₂₂O₄	V = 1527.88 (10) Å³
M_r = 302.36	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1465 (3) Å	µ = 0.09 mm⁻¹
b = 10.0346 (4) Å	T = 293 K
c = 16.6469 (6) Å	0.35 × 0.30 × 0.29 mm

Data collection top

Bruker SMART CCD area detector diffractometer	1734 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1560 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.962	R_int = 0.026
12383 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
1734 reflections	Δρ_min = −0.17 e Å⁻³
203 parameters

Special details top

Experimental. IR (KBr) 3488, 2929, 2901, 2875, 1685, 1455, 1332, 1268, 1215, 1145, 1094, 1072, 1044, 1024, 948, 715 cm^{-1. 1}NMR (CDCl3) 7.28–7.39 (m, 5H), 4.68–4.70(m, 1H), 3.92–3.95(m, 2H), 3.89 (d, J = 1.5 Hz, 1H), 3.80–3.87 (m, 2H), 2.59–2.63 (m, 2H), 2.51–2.55 (m, 2H), 1.96 (s, 1H), 1.80–1.83 (m, 3H), 1.64–1.67 (m, 1H), 1.52–1.57 (m, 2H) p.p.m.. ¹³CNMR (CDCl3) 213.2, 141.3, 128.6, 128.2, 127.1, 107.3, 74.6, 64.4, 63.4, 60.1, 45.1, 41.0, 40.1, 30.5, 29.2, 28.4 p.p.m..

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.6491 (3)	0.0825 (2)	0.69986 (12)	0.0753 (7)
O2	0.5859 (3)	−0.1011 (2)	0.62676 (11)	0.0652 (6)
O3	0.4901 (2)	−0.27188 (15)	0.47755 (10)	0.0465 (5)
O4	0.1336 (2)	−0.00830 (19)	0.44707 (11)	0.0497 (5)
C1	0.6058 (3)	0.0396 (3)	0.62152 (15)	0.0506 (7)
C2	0.7289 (3)	0.0663 (3)	0.56347 (16)	0.0496 (7)
H2A	0.8089	0.0059	0.5752	0.060*
H2B	0.7640	0.1565	0.5717	0.060*
C3	0.6849 (3)	0.0497 (3)	0.47526 (15)	0.0454 (6)
H3	0.7658	0.0822	0.4420	0.054*
C4	0.5513 (3)	0.1339 (3)	0.45651 (16)	0.0484 (6)
H4A	0.5262	0.1253	0.4001	0.058*
H4B	0.5720	0.2269	0.4675	0.058*
C5	0.4239 (3)	0.0869 (2)	0.50846 (16)	0.0428 (6)
H5	0.3392	0.1433	0.4965	0.051*
C6	0.4659 (3)	0.1088 (3)	0.59727 (17)	0.0550 (7)
H6A	0.4764	0.2037	0.6069	0.066*
H6B	0.3869	0.0767	0.6310	0.066*
C7	0.6542 (3)	−0.0947 (3)	0.45113 (15)	0.0431 (6)
H7A	0.6618	−0.1010	0.3931	0.052*
H7B	0.7305	−0.1503	0.4738	0.052*
C8	0.5093 (3)	−0.1518 (2)	0.47572 (13)	0.0351 (5)
C9	0.3807 (3)	−0.0595 (2)	0.49186 (13)	0.0340 (5)
H9	0.3354	−0.0919	0.5415	0.041*
C10	0.6360 (6)	−0.0235 (4)	0.75276 (19)	0.0986 (15)
H10A	0.5687	−0.0013	0.7958	0.118*
H10B	0.7303	−0.0448	0.7762	0.118*
C11	0.5806 (4)	−0.1374 (4)	0.70659 (17)	0.0695 (10)
H11A	0.6407	−0.2155	0.7160	0.083*
H11B	0.4809	−0.1578	0.7222	0.083*
C12	0.2635 (2)	−0.0783 (2)	0.42468 (14)	0.0361 (5)
H12	0.2395	−0.1734	0.4220	0.043*
C13	0.3099 (2)	−0.0343 (2)	0.34160 (13)	0.0351 (5)
C14	0.3927 (3)	−0.1185 (3)	0.29428 (14)	0.0445 (6)
H14	0.4169	−0.2028	0.3133	0.053*
C15	0.4402 (3)	−0.0792 (3)	0.21877 (16)	0.0559 (7)
H15	0.4965	−0.1369	0.1878	0.067*
C16	0.4044 (3)	0.0444 (3)	0.18965 (17)	0.0598 (8)
H16	0.4362	0.0709	0.1391	0.072*
C17	0.3212 (3)	0.1284 (3)	0.23589 (17)	0.0541 (7)
H17	0.2968	0.2123	0.2163	0.065*
C18	0.2731 (3)	0.0903 (3)	0.31126 (15)	0.0437 (6)
H18	0.2161	0.1481	0.3417	0.052*
H4	0.078 (4)	−0.061 (4)	0.474 (2)	0.085 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1027 (18)	0.0848 (16)	0.0384 (10)	−0.0320 (15)	−0.0114 (11)	−0.0115 (11)
O2	0.1016 (17)	0.0530 (12)	0.0411 (10)	−0.0264 (12)	−0.0194 (11)	0.0094 (9)
O3	0.0556 (11)	0.0299 (9)	0.0539 (10)	0.0049 (8)	−0.0135 (9)	−0.0010 (8)
O4	0.0375 (9)	0.0539 (12)	0.0576 (11)	0.0058 (9)	0.0073 (9)	0.0130 (9)
C1	0.0665 (18)	0.0489 (15)	0.0363 (12)	−0.0176 (14)	−0.0052 (12)	−0.0066 (11)
C2	0.0489 (15)	0.0500 (15)	0.0500 (14)	−0.0117 (13)	−0.0108 (12)	−0.0009 (12)
C3	0.0436 (13)	0.0515 (15)	0.0411 (12)	−0.0118 (12)	0.0011 (11)	0.0048 (12)
C4	0.0596 (15)	0.0357 (13)	0.0499 (14)	−0.0120 (12)	−0.0102 (12)	0.0089 (11)
C5	0.0437 (13)	0.0309 (12)	0.0538 (14)	0.0018 (11)	−0.0048 (11)	−0.0021 (11)
C6	0.0579 (17)	0.0506 (16)	0.0564 (16)	−0.0087 (14)	0.0072 (13)	−0.0189 (13)
C7	0.0390 (13)	0.0511 (15)	0.0391 (12)	0.0030 (12)	−0.0009 (10)	−0.0044 (11)
C8	0.0421 (12)	0.0352 (12)	0.0281 (10)	0.0014 (10)	−0.0074 (10)	0.0013 (9)
C9	0.0390 (12)	0.0311 (11)	0.0320 (10)	−0.0010 (10)	0.0005 (9)	0.0025 (9)
C10	0.128 (4)	0.126 (4)	0.0412 (16)	−0.041 (3)	−0.009 (2)	0.002 (2)
C11	0.082 (2)	0.079 (2)	0.0473 (16)	0.022 (2)	0.0053 (16)	0.0114 (16)
C12	0.0329 (12)	0.0333 (12)	0.0422 (12)	−0.0030 (10)	−0.0008 (10)	0.0050 (10)
C13	0.0329 (12)	0.0359 (12)	0.0365 (11)	−0.0049 (10)	−0.0065 (9)	0.0017 (10)
C14	0.0470 (14)	0.0447 (14)	0.0420 (12)	0.0035 (12)	−0.0029 (11)	−0.0007 (11)
C15	0.0582 (17)	0.0692 (19)	0.0403 (14)	0.0010 (16)	0.0036 (12)	−0.0045 (14)
C16	0.0600 (18)	0.080 (2)	0.0393 (13)	−0.0102 (17)	0.0024 (13)	0.0139 (15)
C17	0.0601 (17)	0.0504 (16)	0.0518 (15)	−0.0063 (14)	−0.0077 (13)	0.0182 (13)
C18	0.0473 (14)	0.0395 (13)	0.0445 (13)	−0.0006 (11)	−0.0043 (11)	0.0046 (11)

Geometric parameters (Å, º) top

O1—C10	1.386 (4)	C7—H7A	0.9700
O1—C1	1.429 (3)	C7—H7B	0.9700
O2—C11	1.379 (3)	C8—C9	1.521 (3)
O2—C1	1.425 (3)	C9—C12	1.561 (3)
O3—C8	1.218 (3)	C9—H9	0.9800
O4—C12	1.430 (3)	C10—C11	1.467 (5)
O4—H4	0.86 (4)	C10—H10A	0.9700
C1—C2	1.508 (4)	C10—H10B	0.9700
C1—C6	1.511 (4)	C11—H11A	0.9700
C2—C3	1.532 (4)	C11—H11B	0.9700
C2—H2A	0.9700	C12—C13	1.513 (3)
C2—H2B	0.9700	C12—H12	0.9800
C3—C4	1.518 (4)	C13—C14	1.381 (3)
C3—C7	1.529 (4)	C13—C18	1.390 (3)
C3—H3	0.9800	C14—C15	1.387 (4)
C4—C5	1.526 (4)	C14—H14	0.9300
C4—H4A	0.9700	C15—C16	1.371 (4)
C4—H4B	0.9700	C15—H15	0.9300
C5—C6	1.543 (4)	C16—C17	1.372 (4)
C5—C9	1.546 (3)	C16—H16	0.9300
C5—H5	0.9800	C17—C18	1.384 (4)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—H18	0.9300
C7—C8	1.500 (3)

C10—O1—C1	108.9 (2)	O3—C8—C7	120.8 (2)
C11—O2—C1	109.0 (2)	O3—C8—C9	119.1 (2)
C12—O4—H4	109 (2)	C7—C8—C9	119.91 (19)
O2—C1—O1	106.1 (2)	C8—C9—C5	114.35 (19)
O2—C1—C2	108.1 (2)	C8—C9—C12	109.31 (18)
O1—C1—C2	108.9 (2)	C5—C9—C12	114.77 (18)
O2—C1—C6	111.3 (2)	C8—C9—H9	105.9
O1—C1—C6	109.9 (2)	C5—C9—H9	105.9
C2—C1—C6	112.3 (2)	C12—C9—H9	105.9
C1—C2—C3	113.5 (2)	O1—C10—C11	107.1 (3)
C1—C2—H2A	108.9	O1—C10—H10A	110.3
C3—C2—H2A	108.9	C11—C10—H10A	110.3
C1—C2—H2B	108.9	O1—C10—H10B	110.3
C3—C2—H2B	108.9	C11—C10—H10B	110.3
H2A—C2—H2B	107.7	H10A—C10—H10B	108.5
C4—C3—C7	109.0 (2)	O2—C11—C10	106.7 (3)
C4—C3—C2	110.3 (2)	O2—C11—H11A	110.4
C7—C3—C2	113.8 (2)	C10—C11—H11A	110.4
C4—C3—H3	107.8	O2—C11—H11B	110.4
C7—C3—H3	107.8	C10—C11—H11B	110.4
C2—C3—H3	107.8	H11A—C11—H11B	108.6
C3—C4—C5	109.0 (2)	O4—C12—C13	109.15 (19)
C3—C4—H4A	109.9	O4—C12—C9	108.93 (19)
C5—C4—H4A	109.9	C13—C12—C9	115.27 (18)
C3—C4—H4B	109.9	O4—C12—H12	107.7
C5—C4—H4B	109.9	C13—C12—H12	107.7
H4A—C4—H4B	108.3	C9—C12—H12	107.7
C4—C5—C6	108.0 (2)	C14—C13—C18	118.4 (2)
C4—C5—C9	112.8 (2)	C14—C13—C12	119.8 (2)
C6—C5—C9	111.7 (2)	C18—C13—C12	121.8 (2)
C4—C5—H5	108.1	C13—C14—C15	121.0 (3)
C6—C5—H5	108.1	C13—C14—H14	119.5
C9—C5—H5	108.1	C15—C14—H14	119.5
C1—C6—C5	113.7 (2)	C16—C15—C14	120.1 (3)
C1—C6—H6A	108.8	C16—C15—H15	119.9
C5—C6—H6A	108.8	C14—C15—H15	119.9
C1—C6—H6B	108.8	C15—C16—C17	119.4 (3)
C5—C6—H6B	108.8	C15—C16—H16	120.3
H6A—C6—H6B	107.7	C17—C16—H16	120.3
C8—C7—C3	116.9 (2)	C16—C17—C18	121.0 (3)
C8—C7—H7A	108.1	C16—C17—H17	119.5
C3—C7—H7A	108.1	C18—C17—H17	119.5
C8—C7—H7B	108.1	C17—C18—C13	120.1 (3)
C3—C7—H7B	108.1	C17—C18—H18	119.9
H7A—C7—H7B	107.3	C13—C18—H18	119.9

C11—O2—C1—O1	14.4 (4)	O3—C8—C9—C12	−64.0 (3)
C11—O2—C1—C2	131.1 (3)	C7—C8—C9—C12	110.9 (2)
C11—O2—C1—C6	−105.2 (3)	C4—C5—C9—C8	37.9 (3)
C10—O1—C1—O2	−8.1 (4)	C6—C5—C9—C8	−83.9 (3)
C10—O1—C1—C2	−124.2 (3)	C4—C5—C9—C12	−89.6 (2)
C10—O1—C1—C6	112.4 (3)	C6—C5—C9—C12	148.6 (2)
O2—C1—C2—C3	76.3 (3)	C1—O1—C10—C11	−0.8 (5)
O1—C1—C2—C3	−168.8 (2)	C1—O2—C11—C10	−14.8 (4)
C6—C1—C2—C3	−46.9 (3)	O1—C10—C11—O2	9.6 (5)
C1—C2—C3—C4	53.7 (3)	C8—C9—C12—O4	170.56 (19)
C1—C2—C3—C7	−69.2 (3)	C5—C9—C12—O4	−59.4 (3)
C7—C3—C4—C5	64.1 (3)	C8—C9—C12—C13	−66.4 (2)
C2—C3—C4—C5	−61.5 (3)	C5—C9—C12—C13	63.6 (3)
C3—C4—C5—C6	62.2 (3)	O4—C12—C13—C14	−154.8 (2)
C3—C4—C5—C9	−61.7 (3)	C9—C12—C13—C14	82.3 (3)
O2—C1—C6—C5	−72.3 (3)	O4—C12—C13—C18	26.0 (3)
O1—C1—C6—C5	170.5 (2)	C9—C12—C13—C18	−96.9 (3)
C2—C1—C6—C5	49.1 (3)	C18—C13—C14—C15	1.1 (4)
C4—C5—C6—C1	−56.8 (3)	C12—C13—C14—C15	−178.2 (2)
C9—C5—C6—C1	67.8 (3)	C13—C14—C15—C16	−0.5 (4)
C4—C3—C7—C8	−45.7 (3)	C14—C15—C16—C17	0.0 (4)
C2—C3—C7—C8	77.9 (3)	C15—C16—C17—C18	0.0 (4)
C3—C7—C8—O3	−161.2 (2)	C16—C17—C18—C13	0.6 (4)
C3—C7—C8—C9	24.0 (3)	C14—C13—C18—C17	−1.1 (4)
O3—C8—C9—C5	165.8 (2)	C12—C13—C18—C17	178.1 (2)
C7—C8—C9—C5	−19.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.86 (4)	2.03 (4)	2.857 (3)	163 (3)
C16—H16···O3ⁱⁱ	0.93	2.59	3.473 (4)	159

Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.86 (4)	2.03 (4)	2.857 (3)	163 (3)
C16—H16···O3ⁱⁱ	0.93	2.59	3.473 (4)	159

Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NSFC 21206147, 21376224).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, W., LaCour, T. G. & Fuchs, P. L. (2002). J. Am. Chem. Soc. 124, 4548–4549. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lopez-Alvarado, P., Garcia-Granda, S., Alvarez-Rua, C. & Avendano, C. (2002). Eur. J. Org. Chem. pp. 1702–1707. Google Scholar
Shallard-Brown, H. A., Watkin, D. J. & Cowley, A. R. (2005). Acta Cryst. E61, o2424–o2425. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 70| Part 6| June 2014| Page o665

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

7,7-[Ethane-1,2-diylbis(­oxy)]-2-[hy­droxy(phenyl)methyl]bi­cyclo[3.3.1]nonan-3-one

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organic compounds

7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one