3,9-Di-2-furyl-2,4,8,10-tetra-oxa-spiro-[5.5]undecane.

The title compound, C(15)H(16)O(6), was prepared by reaction of 2,2-bis-(hydroxy-meth-yl)propane-1,3-diol with 2-furaldehyde in the presence of hydro-chloric acid at room temperature. The asymmetric unit contains two crystallographically independent mol-ecules. In these two mol-ecules, the dihedral angles between the five-membered rings are 56.4 (3) and 56.3 (3)°. The six-membered rings adopt chair conformations. Inter-molecular C-H⋯π inter-actions link the mol-ecules and may be effective in the stabilization of the crystal structure.

Related literature

For background on di-acetals of penta­erythritol, see: Jermy & Pandurangan (2005 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H16O6

M = 292.28

Orthorhombic,

a = 11.756 (3) Å

b = 5.5832 (13) Å

c = 42.728 (9) Å

V = 2804.5 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 273 (2) K

0.20 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

13819 measured reflections

3554 independent reflections

1793 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.125

S = 1.02

3554 reflections

380 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032996/at2637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032996/at2637Isup2.hkl

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

C15H16O6	F(000) = 1232
Mr = 292.28	Dx = 1.384 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2523 reflections
a = 11.756 (3) Å	θ = 1.9–28.8°
b = 5.5832 (13) Å	µ = 0.11 mm−1
c = 42.728 (9) Å	T = 273 K
V = 2804.5 (11) Å3	Bar, colourless
Z = 8	0.20 × 0.15 × 0.13 mm

Bruker SMART CCD area-detector diffractometer	1793 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
graphite	θmax = 28.8°, θmin = 1.9°
φ and ω scans	h = −15→15
13819 measured reflections	k = −7→6
3554 independent reflections	l = −28→57

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3554 reflections	Δρmax = 0.17 e Å−3
380 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (7)

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
O1A	−0.9377 (3)	−0.0310 (7)	−0.19447 (12)	0.0640 (12)
O2A	−0.7186 (2)	−0.2654 (6)	−0.14554 (7)	0.0511 (8)
O3A	−0.8254 (3)	0.0757 (7)	−0.13372 (8)	0.0497 (8)
O4A	−0.4986 (2)	−0.0918 (6)	−0.06685 (8)	0.0501 (8)
O5A	−0.6606 (2)	−0.3243 (5)	−0.06050 (7)	0.0485 (8)
O6A	−0.5577 (3)	−0.5078 (7)	−0.00488 (13)	0.0686 (14)
C1A	−1.0251 (4)	−0.1649 (13)	−0.20675 (12)	0.0699 (17)
H1	−1.0780	−0.1086	−0.2212	0.084*
C2A	−1.0235 (5)	−0.3856 (14)	−0.19522 (15)	0.0729 (17)
H2	−1.0737	−0.5093	−0.1999	0.087*
C3A	−0.9290 (4)	−0.3953 (12)	−0.17413 (12)	0.0610 (14)
H3A	−0.9060	−0.5269	−0.1624	0.073*
C4A	−0.8807 (4)	−0.1810 (9)	−0.17450 (11)	0.0493 (13)
C5A	−0.7824 (4)	−0.0747 (10)	−0.15763 (12)	0.0488 (12)
H3	−0.7358	0.0191	−0.1722	0.059*
C6A	−0.6229 (3)	−0.1810 (9)	−0.12730 (11)	0.0498 (12)
H4	−0.5708	−0.0946	−0.1408	0.060*
H5	−0.5825	−0.3170	−0.1186	0.060*
C7A	−0.7335 (4)	0.1789 (9)	−0.11575 (12)	0.0529 (13)
H6	−0.7644	0.2807	−0.0994	0.063*
H7	−0.6864	0.2770	−0.1293	0.063*
C8A	−0.6613 (4)	−0.0183 (8)	−0.10104 (15)	0.0406 (15)
C9A	−0.5593 (4)	0.0911 (10)	−0.08414 (13)	0.0564 (13)
H8	−0.5086	0.1644	−0.0993	0.068*
H9	−0.5852	0.2148	−0.0699	0.068*
C10A	−0.7312 (3)	−0.1575 (8)	−0.07684 (11)	0.0479 (12)
H10A	−0.7649	−0.0464	−0.0620	0.058*
H10B	−0.7923	−0.2426	−0.0873	0.058*
C11A	−0.5709 (4)	−0.2040 (8)	−0.04513 (11)	0.0466 (11)
H11A	−0.6017	−0.0853	−0.0305	0.056*
C12A	−0.5016 (3)	−0.3830 (8)	−0.02793 (10)	0.0429 (11)
C13A	−0.3940 (4)	−0.4551 (11)	−0.02931 (16)	0.0567 (16)
H13A	−0.3380	−0.3968	−0.0427	0.068*
C14A	−0.3807 (4)	−0.6389 (9)	−0.00639 (13)	0.0592 (14)
H14A	−0.3146	−0.7240	−0.0020	0.071*
C15A	−0.4803 (5)	−0.6641 (10)	0.00723 (13)	0.0683 (16)
H15A	−0.4958	−0.7740	0.0230	0.082*
O1C	−0.8218 (3)	0.0078 (6)	−0.44998 (13)	0.0703 (15)
O2C	−0.7613 (2)	−0.4102 (6)	−0.38836 (8)	0.0505 (8)
O3C	−0.9241 (2)	−0.1758 (5)	−0.39479 (7)	0.0472 (8)
O4C	−0.9819 (2)	−0.2334 (6)	−0.31003 (7)	0.0522 (8)
O5C	−1.0889 (3)	−0.5735 (6)	−0.32170 (8)	0.0488 (8)
O6C	−1.1999 (3)	−0.4592 (7)	−0.25972 (11)	0.0637 (12)
C1C	−0.7431 (5)	0.1642 (10)	−0.46269 (13)	0.0670 (15)
H10	−0.7580	0.2719	−0.4788	0.080*
C2C	−0.6432 (4)	0.1384 (9)	−0.44859 (13)	0.0594 (14)
H11	−0.5771	0.2238	−0.4529	0.071*
C3C	−0.6563 (4)	−0.0432 (10)	−0.42592 (15)	0.0525 (14)
H12	−0.6004	−0.1010	−0.4125	0.063*
C4C	−0.7649 (4)	−0.1166 (9)	−0.42743 (11)	0.0467 (12)
C5C	−0.8333 (3)	−0.2969 (8)	−0.40988 (12)	0.0486 (12)
H13	−0.8641	−0.4157	−0.4245	0.058*
C6C	−0.8220 (4)	−0.5912 (10)	−0.37114 (13)	0.0545 (13)
H14	−0.7716	−0.6637	−0.3559	0.065*
H15	−0.8473	−0.7156	−0.3854	0.065*
C7C	−0.9949 (3)	−0.3431 (8)	−0.37802 (11)	0.0492 (13)
H16	−1.0294	−0.4539	−0.3927	0.059*
H17	−1.0553	−0.2570	−0.3674	0.059*
C8C	−0.9258 (4)	−0.4814 (8)	−0.35426 (16)	0.0446 (16)
C9C	−0.8853 (3)	−0.3187 (9)	−0.32749 (11)	0.0486 (12)
H18	−0.8349	−0.4075	−0.3138	0.058*
H19	−0.8434	−0.1839	−0.3360	0.058*
C10C	−0.9987 (4)	−0.6797 (8)	−0.33978 (13)	0.0540 (13)
H10C	−1.0306	−0.7793	−0.3562	0.065*
H10D	−0.9520	−0.7800	−0.3264	0.065*
C11C	−1.0466 (4)	−0.4235 (10)	−0.29762 (12)	0.0445 (11)
H11B	−1.0004	−0.5173	−0.2830	0.053*
C12C	−1.1446 (4)	−0.3143 (9)	−0.28089 (11)	0.0502 (13)
C13C	−1.1951 (4)	−0.0968 (11)	−0.28203 (12)	0.0587 (14)
H13B	−1.1740	0.0319	−0.2946	0.070*
C14C	−1.2866 (4)	−0.1037 (14)	−0.26034 (13)	0.0701 (15)
H14C	−1.3370	0.0201	−0.2559	0.084*
C15C	−1.2864 (4)	−0.3213 (13)	−0.24756 (13)	0.0708 (17)
H15B	−1.3377	−0.3731	−0.2324	0.085*

	U11	U22	U33	U12	U13	U23
O1A	0.056 (2)	0.081 (3)	0.055 (3)	−0.0011 (19)	−0.010 (2)	0.012 (2)
O2A	0.0440 (17)	0.049 (2)	0.0598 (19)	0.0066 (15)	−0.0060 (16)	−0.0094 (16)
O3A	0.0468 (18)	0.047 (2)	0.055 (2)	0.0073 (16)	−0.0066 (17)	−0.002 (2)
O4A	0.0347 (16)	0.053 (2)	0.063 (2)	−0.0062 (14)	−0.0055 (16)	0.007 (2)
O5A	0.0325 (16)	0.052 (2)	0.0610 (18)	−0.0038 (13)	−0.0051 (15)	0.0122 (16)
O6A	0.045 (2)	0.091 (4)	0.070 (3)	0.0075 (18)	0.005 (2)	0.032 (2)
C1A	0.050 (3)	0.104 (6)	0.056 (4)	−0.002 (3)	−0.012 (3)	−0.006 (3)
C2A	0.059 (4)	0.077 (5)	0.083 (4)	−0.010 (3)	−0.010 (3)	−0.020 (4)
C3A	0.058 (3)	0.062 (4)	0.062 (3)	−0.007 (3)	−0.011 (3)	−0.004 (3)
C4A	0.043 (3)	0.058 (4)	0.047 (3)	0.002 (2)	−0.005 (2)	0.002 (2)
C5A	0.043 (3)	0.051 (3)	0.053 (3)	0.004 (2)	0.003 (2)	0.006 (3)
C6A	0.038 (3)	0.059 (3)	0.052 (3)	0.003 (2)	0.002 (2)	0.004 (2)
C7A	0.053 (3)	0.046 (3)	0.060 (3)	−0.003 (2)	−0.015 (3)	−0.002 (3)
C8A	0.032 (2)	0.040 (4)	0.050 (4)	0.0023 (18)	−0.004 (2)	−0.001 (2)
C9A	0.053 (3)	0.043 (3)	0.073 (4)	−0.006 (2)	−0.015 (3)	0.000 (3)
C10A	0.034 (2)	0.053 (3)	0.057 (3)	0.009 (2)	−0.007 (2)	0.005 (2)
C11A	0.042 (3)	0.052 (3)	0.046 (3)	0.000 (2)	−0.005 (2)	−0.001 (2)
C12A	0.036 (2)	0.053 (3)	0.040 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C13A	0.045 (3)	0.062 (4)	0.063 (4)	0.004 (2)	0.010 (3)	0.010 (3)
C14A	0.052 (3)	0.065 (4)	0.061 (4)	0.008 (2)	−0.014 (3)	0.002 (3)
C15A	0.058 (3)	0.081 (4)	0.066 (4)	−0.002 (3)	−0.007 (3)	0.025 (3)
O1C	0.0427 (19)	0.092 (4)	0.076 (3)	0.0014 (17)	−0.001 (2)	0.032 (2)
O2C	0.0375 (16)	0.052 (2)	0.062 (2)	0.0069 (15)	0.0041 (17)	0.008 (2)
O3C	0.0334 (16)	0.053 (2)	0.0553 (18)	0.0017 (14)	0.0044 (14)	0.0040 (16)
O4C	0.0429 (18)	0.051 (2)	0.062 (2)	−0.0053 (15)	0.0059 (16)	−0.0054 (17)
O5C	0.0437 (18)	0.0462 (19)	0.057 (2)	−0.0067 (16)	0.0043 (17)	−0.001 (2)
O6C	0.061 (2)	0.074 (3)	0.056 (3)	−0.0053 (18)	0.009 (2)	0.007 (2)
C1C	0.058 (3)	0.076 (4)	0.068 (3)	−0.001 (3)	0.012 (3)	0.032 (3)
C2C	0.052 (3)	0.062 (4)	0.064 (4)	−0.011 (2)	−0.001 (3)	0.004 (3)
C3C	0.041 (3)	0.065 (4)	0.051 (4)	−0.005 (2)	0.000 (3)	0.003 (3)
C4C	0.040 (3)	0.054 (3)	0.046 (3)	−0.001 (2)	0.001 (2)	0.002 (3)
C5C	0.037 (2)	0.051 (3)	0.058 (3)	0.003 (2)	0.004 (2)	−0.004 (2)
C6C	0.048 (3)	0.050 (3)	0.066 (3)	0.006 (2)	0.012 (3)	0.008 (3)
C7C	0.035 (2)	0.053 (3)	0.060 (3)	−0.003 (2)	−0.002 (2)	0.002 (2)
C8C	0.042 (3)	0.034 (3)	0.058 (4)	−0.0001 (18)	0.001 (3)	0.001 (2)
C9C	0.031 (2)	0.058 (3)	0.057 (3)	−0.002 (2)	0.004 (2)	−0.005 (2)
C10C	0.057 (3)	0.042 (3)	0.063 (3)	−0.004 (2)	0.012 (3)	0.000 (3)
C11C	0.044 (3)	0.048 (3)	0.042 (3)	0.002 (2)	−0.002 (2)	0.006 (3)
C12C	0.047 (3)	0.067 (4)	0.036 (3)	−0.005 (2)	−0.003 (2)	0.005 (2)
C13C	0.058 (3)	0.064 (4)	0.055 (3)	0.013 (3)	0.007 (3)	0.005 (3)
C14C	0.055 (3)	0.095 (5)	0.060 (4)	0.014 (3)	0.005 (3)	−0.011 (4)
C15C	0.048 (3)	0.106 (5)	0.059 (3)	−0.006 (3)	0.015 (3)	−0.011 (4)

O1A—C4A	1.370 (6)	O1C—C4C	1.363 (6)
O1A—C1A	1.374 (7)	O1C—C1C	1.383 (6)
O2A—C5A	1.401 (6)	O2C—C5C	1.401 (5)
O2A—C6A	1.448 (5)	O2C—C6C	1.439 (6)
O3A—C5A	1.416 (6)	O3C—C5C	1.418 (5)
O3A—C7A	1.445 (5)	O3C—C7C	1.442 (5)
O4A—C11A	1.405 (5)	O4C—C11C	1.410 (6)
O4A—C9A	1.448 (6)	O4C—C9C	1.439 (5)
O5A—C11A	1.412 (5)	O5C—C11C	1.417 (6)
O5A—C10A	1.430 (5)	O5C—C10C	1.440 (6)
O6A—C15A	1.363 (6)	O6C—C15C	1.377 (7)
O6A—C12A	1.375 (6)	O6C—C12C	1.377 (6)
C1A—C2A	1.327 (9)	C1C—C2C	1.327 (7)
C1A—H1	0.9300	C1C—H10	0.9300
C2A—C3A	1.431 (7)	C2C—C3C	1.411 (8)
C2A—H2	0.9300	C2C—H11	0.9300
C3A—C4A	1.324 (7)	C3C—C4C	1.343 (6)
C3A—H3A	0.9300	C3C—H12	0.9300
C4A—C5A	1.486 (6)	C4C—C5C	1.491 (6)
C5A—H3	0.9800	C5C—H13	0.9800
C6A—C8A	1.512 (8)	C6C—C8C	1.545 (7)
C6A—H4	0.9700	C6C—H14	0.9700
C6A—H5	0.9700	C6C—H15	0.9700
C7A—C8A	1.526 (7)	C7C—C8C	1.512 (7)
C7A—H6	0.9700	C7C—H16	0.9700
C7A—H7	0.9700	C7C—H17	0.9700
C8A—C9A	1.528 (7)	C8C—C10C	1.531 (7)
C8A—C10A	1.532 (7)	C8C—C9C	1.536 (8)
C9A—H8	0.9700	C9C—H18	0.9700
C9A—H9	0.9700	C9C—H19	0.9700
C10A—H10A	0.9700	C10C—H10C	0.9700
C10A—H10B	0.9700	C10C—H10D	0.9700
C11A—C12A	1.484 (6)	C11C—C12C	1.487 (7)
C11A—H11A	0.9800	C11C—H11B	0.9800
C12A—C13A	1.328 (6)	C12C—C13C	1.352 (7)
C13A—C14A	1.427 (8)	C13C—C14C	1.420 (7)
C13A—H13A	0.9300	C13C—H13B	0.9300
C14A—C15A	1.315 (6)	C14C—C15C	1.332 (8)
C14A—H14A	0.9300	C14C—H14C	0.9300
C15A—H15A	0.9300	C15C—H15B	0.9300
C4A—O1A—C1A	105.7 (5)	C4C—O1C—C1C	105.7 (4)
C5A—O2A—C6A	111.5 (4)	C5C—O2C—C6C	110.7 (3)
C5A—O3A—C7A	110.7 (3)	C5C—O3C—C7C	110.6 (3)
C11A—O4A—C9A	110.7 (3)	C11C—O4C—C9C	111.8 (4)
C11A—O5A—C10A	110.5 (3)	C11C—O5C—C10C	112.0 (3)
C15A—O6A—C12A	106.0 (4)	C15C—O6C—C12C	105.5 (5)
C2A—C1A—O1A	110.7 (5)	C2C—C1C—O1C	110.2 (5)
C2A—C1A—H1	124.7	C2C—C1C—H10	124.9
O1A—C1A—H1	124.7	O1C—C1C—H10	124.9
C1A—C2A—C3A	106.2 (6)	C1C—C2C—C3C	107.0 (4)
C1A—C2A—H2	126.9	C1C—C2C—H11	126.5
C3A—C2A—H2	126.9	C3C—C2C—H11	126.5
C4A—C3A—C2A	106.9 (6)	C4C—C3C—C2C	106.9 (5)
C4A—C3A—H3A	126.5	C4C—C3C—H12	126.6
C2A—C3A—H3A	126.5	C2C—C3C—H12	126.6
C3A—C4A—O1A	110.5 (4)	C3C—C4C—O1C	110.2 (5)
C3A—C4A—C5A	133.5 (5)	C3C—C4C—C5C	134.0 (5)
O1A—C4A—C5A	116.0 (5)	O1C—C4C—C5C	115.8 (4)
O2A—C5A—O3A	112.1 (4)	O2C—C5C—O3C	111.8 (4)
O2A—C5A—C4A	107.0 (4)	O2C—C5C—C4C	108.0 (4)
O3A—C5A—C4A	108.0 (3)	O3C—C5C—C4C	108.2 (4)
O2A—C5A—H3	109.9	O2C—C5C—H13	109.6
O3A—C5A—H3	109.9	O3C—C5C—H13	109.6
C4A—C5A—H3	109.9	C4C—C5C—H13	109.6
O2A—C6A—C8A	111.3 (3)	O2C—C6C—C8C	110.6 (4)
O2A—C6A—H4	109.4	O2C—C6C—H14	109.5
C8A—C6A—H4	109.4	C8C—C6C—H14	109.5
O2A—C6A—H5	109.4	O2C—C6C—H15	109.5
C8A—C6A—H5	109.4	C8C—C6C—H15	109.5
H4—C6A—H5	108.0	H14—C6C—H15	108.1
O3A—C7A—C8A	110.3 (4)	O3C—C7C—C8C	110.8 (3)
O3A—C7A—H6	109.6	O3C—C7C—H16	109.5
C8A—C7A—H6	109.6	C8C—C7C—H16	109.5
O3A—C7A—H7	109.6	O3C—C7C—H17	109.5
C8A—C7A—H7	109.6	C8C—C7C—H17	109.5
H6—C7A—H7	108.1	H16—C7C—H17	108.1
C6A—C8A—C9A	110.8 (4)	C7C—C8C—C10C	109.9 (4)
C6A—C8A—C7A	107.1 (5)	C7C—C8C—C9C	111.4 (4)
C9A—C8A—C7A	110.0 (4)	C10C—C8C—C9C	107.5 (5)
C6A—C8A—C10A	110.9 (4)	C7C—C8C—C6C	108.3 (5)
C9A—C8A—C10A	107.7 (5)	C10C—C8C—C6C	110.1 (4)
C7A—C8A—C10A	110.2 (4)	C9C—C8C—C6C	109.7 (4)
O4A—C9A—C8A	110.2 (4)	O4C—C9C—C8C	109.7 (3)
O4A—C9A—H8	109.6	O4C—C9C—H18	109.7
C8A—C9A—H8	109.6	C8C—C9C—H18	109.7
O4A—C9A—H9	109.6	O4C—C9C—H19	109.7
C8A—C9A—H9	109.6	C8C—C9C—H19	109.7
H8—C9A—H9	108.1	H18—C9C—H19	108.2
O5A—C10A—C8A	110.4 (3)	O5C—C10C—C8C	109.3 (4)
O5A—C10A—H10A	109.6	O5C—C10C—H10C	109.8
C8A—C10A—H10A	109.6	C8C—C10C—H10C	109.8
O5A—C10A—H10B	109.6	O5C—C10C—H10D	109.8
C8A—C10A—H10B	109.6	C8C—C10C—H10D	109.8
H10A—C10A—H10B	108.1	H10C—C10C—H10D	108.3
O4A—C11A—O5A	110.9 (4)	O4C—C11C—O5C	111.2 (4)
O4A—C11A—C12A	107.2 (3)	O4C—C11C—C12C	106.9 (4)
O5A—C11A—C12A	108.7 (4)	O5C—C11C—C12C	108.7 (4)
O4A—C11A—H11A	110.0	O4C—C11C—H11B	110.0
O5A—C11A—H11A	110.0	O5C—C11C—H11B	110.0
C12A—C11A—H11A	110.0	C12C—C11C—H11B	110.0
C13A—C12A—O6A	109.6 (5)	C13C—C12C—O6C	110.1 (5)
C13A—C12A—C11A	134.8 (5)	C13C—C12C—C11C	133.7 (5)
O6A—C12A—C11A	115.6 (4)	O6C—C12C—C11C	116.2 (5)
C12A—C13A—C14A	107.0 (5)	C12C—C13C—C14C	106.5 (6)
C12A—C13A—H13A	126.5	C12C—C13C—H13B	126.7
C14A—C13A—H13A	126.5	C14C—C13C—H13B	126.7
C15A—C14A—C13A	106.4 (5)	C15C—C14C—C13C	106.9 (6)
C15A—C14A—H14A	126.8	C15C—C14C—H14C	126.6
C13A—C14A—H14A	126.8	C13C—C14C—H14C	126.6
C14A—C15A—O6A	111.0 (5)	C14C—C15C—O6C	110.9 (5)
C14A—C15A—H15A	124.5	C14C—C15C—H15B	124.5
O6A—C15A—H15A	124.5	O6C—C15C—H15B	124.5

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1···Cg1	0.93	2.70	3.478 (6)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O6C/C12C–C15C ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1⋯Cg1	0.93	2.70	3.478 (6)	142