6,10,16,19-Tetra-oxatrispiro-[4.2.2.4.2.2]nona-deca-ne.

The asymmetric unit of the title compound, C(15)H(24)O(4), contains one half-mol-ecule; a twofold rotation axis passes through the central C atom. The non-planar six- and five-membered rings adopt chair and envelope conformations, respectively. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Jermy & Pandurangan (2005 ▶). For related literature, see: Sun et al. (2001 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H24O4

M = 268.34

Monoclinic,

a = 25.605 (5) Å

b = 5.5820 (11) Å

c = 10.337 (2) Å

β = 90.22 (3)°

V = 1477.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.982

1547 measured reflections

1457 independent reflections

864 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.173

S = 0.93

1457 reflections

87 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001785/hk2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001785/hk2414Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H24O4	F000 = 584
Mr = 268.34	Dx = 1.206 Mg m−3
Monoclinic, C2/c	Melting point: 401 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 25.605 (5) Å	Cell parameters from 25 reflections
b = 5.5820 (11) Å	θ = 10–13º
c = 10.337 (2) Å	µ = 0.09 mm−1
β = 90.22 (3)º	T = 294 (2) K
V = 1477.4 (5) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.6º
T = 294(2) K	h = −31→31
ω/2θ scans	k = 0→6
Absorption correction: ψ scan(North et al., 1968)	l = 0→12
Tmin = 0.965, Tmax = 0.982	3 standard reflections
1547 measured reflections	every 120 min
1457 independent reflections	intensity decay: none
864 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.06P)2 + 4.5P] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
1457 reflections	Δρmax = 0.26 e Å−3
87 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.43380 (7)	0.3857 (4)	0.41870 (16)	0.0381 (5)
O2	0.42692 (7)	0.0861 (3)	0.26166 (16)	0.0324 (5)
C1	0.30826 (17)	0.3438 (9)	0.3294 (5)	0.0889 (15)
H1A	0.2819	0.3125	0.2638	0.107*
H1B	0.2974	0.4816	0.3797	0.107*
C2	0.31481 (15)	0.1237 (9)	0.4179 (4)	0.0803 (13)
H2A	0.2973	0.1514	0.4996	0.096*
H2B	0.2993	−0.0159	0.3773	0.096*
C3	0.36848 (12)	0.0842 (7)	0.4393 (3)	0.0503 (9)
H3A	0.3768	−0.0835	0.4262	0.060*
H3B	0.3777	0.1271	0.5274	0.060*
C4	0.35773 (13)	0.3897 (7)	0.2697 (3)	0.0567 (10)
H4A	0.3662	0.5588	0.2750	0.068*
H4B	0.3567	0.3436	0.1792	0.068*
C5	0.39900 (11)	0.2397 (5)	0.3435 (3)	0.0336 (7)
C6	0.46853 (11)	0.5234 (5)	0.3396 (2)	0.0342 (7)
H6A	0.4922	0.6138	0.3945	0.041*
H6B	0.4484	0.6366	0.2884	0.041*
C7	0.5000	0.3637 (7)	0.2500	0.0278 (8)
C8	0.46173 (10)	0.2072 (5)	0.1738 (2)	0.0337 (7)
H8A	0.4417	0.3060	0.1145	0.040*
H8B	0.4809	0.0901	0.1235	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0461 (12)	0.0405 (12)	0.0275 (9)	0.0017 (10)	−0.0016 (8)	−0.0038 (9)
O2	0.0368 (10)	0.0236 (10)	0.0368 (10)	−0.0008 (9)	0.0005 (8)	−0.0038 (8)
C1	0.076 (3)	0.098 (4)	0.093 (3)	0.005 (3)	−0.001 (2)	0.016 (3)
C2	0.069 (3)	0.089 (3)	0.083 (3)	−0.005 (3)	0.006 (2)	0.009 (3)
C3	0.052 (2)	0.053 (2)	0.0460 (17)	−0.0121 (17)	0.0100 (15)	−0.0008 (16)
C4	0.057 (2)	0.052 (2)	0.061 (2)	0.0252 (18)	−0.0165 (17)	−0.0025 (17)
C5	0.0338 (14)	0.0256 (15)	0.0413 (15)	0.0057 (12)	−0.0035 (12)	−0.0032 (12)
C6	0.0469 (16)	0.0252 (15)	0.0306 (13)	−0.0021 (13)	−0.0012 (12)	−0.0044 (11)
C7	0.040 (2)	0.023 (2)	0.0204 (16)	0.000	−0.0036 (15)	0.000
C8	0.0393 (15)	0.0322 (16)	0.0296 (13)	−0.0017 (13)	−0.0019 (12)	−0.0004 (12)

O1—C5	1.434 (3)	C3—H3B	0.9700
O1—C6	1.434 (3)	C4—C5	1.547 (4)
O2—C5	1.402 (3)	C4—H4A	0.9700
O2—C8	1.443 (3)	C4—H4B	0.9700
C1—C4	1.434 (5)	C6—C7	1.519 (3)
C1—C2	1.540 (6)	C6—H6A	0.9700
C1—H1A	0.9700	C6—H6B	0.9700
C1—H1B	0.9700	C7—C6i	1.519 (3)
C2—C3	1.408 (5)	C7—C8	1.529 (3)
C2—H2A	0.9700	C7—C8i	1.529 (3)
C2—H2B	0.9700	C8—H8A	0.9700
C3—C5	1.533 (4)	C8—H8B	0.9700
C3—H3A	0.9700
C5—O1—C6	112.37 (19)	H4A—C4—H4B	108.6
C5—O2—C8	114.2 (2)	O2—C5—O1	110.9 (2)
C4—C1—C2	107.7 (4)	O2—C5—C3	107.8 (2)
C4—C1—H1A	110.2	O1—C5—C3	106.8 (2)
C2—C1—H1A	110.2	O2—C5—C4	112.5 (2)
C4—C1—H1B	110.2	O1—C5—C4	112.4 (2)
C2—C1—H1B	110.2	C3—C5—C4	106.0 (3)
H1A—C1—H1B	108.5	O1—C6—C7	111.4 (2)
C3—C2—C1	108.8 (4)	O1—C6—H6A	109.4
C3—C2—H2A	109.9	C7—C6—H6A	109.4
C1—C2—H2A	109.9	O1—C6—H6B	109.4
C3—C2—H2B	109.9	C7—C6—H6B	109.4
C1—C2—H2B	109.9	H6A—C6—H6B	108.0
H2A—C2—H2B	108.3	C6—C7—C6i	108.1 (3)
C2—C3—C5	108.0 (3)	C6—C7—C8	107.99 (15)
C2—C3—H3A	110.1	C6i—C7—C8	111.22 (14)
C5—C3—H3A	110.1	C6—C7—C8i	111.22 (14)
C2—C3—H3B	110.1	C6i—C7—C8i	107.99 (15)
C5—C3—H3B	110.1	C8—C7—C8i	110.3 (3)
H3A—C3—H3B	108.4	O2—C8—C7	109.86 (18)
C1—C4—C5	107.1 (3)	O2—C8—H8A	109.7
C1—C4—H4A	110.3	C7—C8—H8A	109.7
C5—C4—H4A	110.3	O2—C8—H8B	109.7
C1—C4—H4B	110.3	C7—C8—H8B	109.7
C5—C4—H4B	110.3	H8A—C8—H8B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O2ii	0.97	2.58	3.413 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O2i	0.97	2.58	3.413 (4)	143

Symmetry code: (i) .