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

In the title compound, C18H22O4, the cyclo-hexane and cyclo-hexa-none 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, mol-ecules 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.

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 = 302.36

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 1.03

1734 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814009040/is5345sup1.cif

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

CCDC reference: 998726

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H22O4	Dx = 1.314 Mg m−3
Mr = 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

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

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(Fo2) + (0.0446P)2 + 0.4409P] where P = (Fo2 + 2Fc2)/3
1734 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. IR (KBr) 3488, 2929, 2901, 2875, 1685, 1455, 1332, 1268, 1215, 1145, 1094, 1072, 1044, 1024, 948, 715 cm-1. 1NMR (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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .