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Acta Cryst. (2008). E64, o2130    [ doi:10.1107/S1600536808032996 ]

3,9-Di-2-furyl-2,4,8,10-tetraoxaspiro[5.5]undecane

J. Lin and F.-F. Jian

Abstract top

The title compound, C15H16O6, was prepared by reaction of 2,2-bis(hydroxymethyl)propane-1,3-diol with 2-furaldehyde in the presence of hydrochloric acid at room temperature. The asymmetric unit contains two crystallographically independent molecules. In these two molecules, the dihedral angles between the five-membered rings are 56.4 (3) and 56.3 (3)°. The six-membered rings adopt chair conformations. Intermolecular C-H...[pi] interactions link the molecules and may be effective in the stabilization of the crystal structure.

Comment top

The di-acetals of pentaerythritol are a series of useful organic compounds. They have been used as important intermediates in the synthesis of pesticides (Jermy & Pandurangan, 2005). we sythesis the title compound (I) and report its crystal structure here.

In the crystal structure of (I), the asymmetric unit contains two crystallographically independent molecules (Fig. 1). The dihedral angle formed by the ring (O1A/C1A–C4A) and the ring (O6A/C12A–C15A) is 56.4 (3)° and 56.3 (3)° for the ring (O1CA/C1C–C4C) and the ring (O6C/C12C–C15C). The six-membered rings of the two independent molecules of (I), (O2A/O3A/C5A–C8A), (O2C/O3C/C5C–C8C), (O4A/O5A/C8A–C11A) and (O4C/O5C/C8C–C11C) have chair conformations [the puckering parameters: QT = 0.564 (5) Å, φ = 170 (15)°, θ = 0.0 (5)°; QT = 0.563 (5) Å, φ = 244 (10)°, θ = 176.7 (5)°; QT = 0.574 (5) Å, φ = 292 (9)°, θ = 2.3 (5)° and QT = 0.573 (5) Å, φ = 309 (22)°, θ = 178.1 (5)°, respectively (Cremer & Pople, 1975)].

Intermolecular C···H···π link the molecules and may be effective in the stabilization of the crystal structure (Table 1).

Related literature top

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

Experimental top

The title compound (I) was prepared by the process as following: ethyl isonicotinate 1.51 g (0.01 mol) and hydrazine hydrate 0.32 g (0.01 mol) with ethanol at 377 K for 3 h, afford ivory-white compound A 1.32 g (yield 96%), then add 0.06 ml carbon disulfide and KOH 0.56 g(0.01 mol) with ethanol, stirred at room temperature for 5 h, afford yellow compound B 2.0 g (yield 85.6%). At last, add 0.32 g hydrazine hydrate to the compound B with water at 377 K for 12 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from DMF-HCl(3:1) at 334 K.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq of the parent atoms. In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
3,9-Di-2-furyl-2,4,8,10-tetraoxaspiro[5.5]undecane top
Crystal data top
C15H16O6F(000) = 1232
Mr = 292.28Dx = 1.384 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2523 reflections
a = 11.756 (3) Åθ = 1.9–28.8°
b = 5.5832 (13) ŵ = 0.11 mm−1
c = 42.728 (9) ÅT = 273 K
V = 2804.5 (11) Å3Bar, colourless
Z = 80.20 × 0.15 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1793 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
graphiteθmax = 28.8°, θmin = 1.9°
φ and ω scansh = −15→15
13819 measured reflectionsk = −7→6
3554 independent reflectionsl = −28→57
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-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 reflectionsΔρmax = 0.17 e Å−3
380 parametersΔρmin = −0.17 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (7)
Crystal data top
C15H16O6V = 2804.5 (11) Å3
Mr = 292.28Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 11.756 (3) ŵ = 0.11 mm−1
b = 5.5832 (13) ÅT = 273 K
c = 42.728 (9) Å0.20 × 0.15 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1793 reflections with I > 2σ(I)
13819 measured reflectionsRint = 0.069
3554 independent reflectionsθmax = 28.8°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.125Δρmax = 0.17 e Å−3
S = 1.02Δρmin = −0.17 e Å−3
3554 reflectionsAbsolute structure: ?
380 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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
xyzUiso*/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)
H1−1.0780−0.1086−0.22120.084*
C2A−1.0235 (5)−0.3856 (14)−0.19522 (15)0.0729 (17)
H2−1.0737−0.5093−0.19990.087*
C3A−0.9290 (4)−0.3953 (12)−0.17413 (12)0.0610 (14)
H3A−0.9060−0.5269−0.16240.073*
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)
H3−0.73580.0191−0.17220.059*
C6A−0.6229 (3)−0.1810 (9)−0.12730 (11)0.0498 (12)
H4−0.5708−0.0946−0.14080.060*
H5−0.5825−0.3170−0.11860.060*
C7A−0.7335 (4)0.1789 (9)−0.11575 (12)0.0529 (13)
H6−0.76440.2807−0.09940.063*
H7−0.68640.2770−0.12930.063*
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)
H8−0.50860.1644−0.09930.068*
H9−0.58520.2148−0.06990.068*
C10A−0.7312 (3)−0.1575 (8)−0.07684 (11)0.0479 (12)
H10A−0.7649−0.0464−0.06200.058*
H10B−0.7923−0.2426−0.08730.058*
C11A−0.5709 (4)−0.2040 (8)−0.04513 (11)0.0466 (11)
H11A−0.6017−0.0853−0.03050.056*
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−0.3380−0.3968−0.04270.068*
C14A−0.3807 (4)−0.6389 (9)−0.00639 (13)0.0592 (14)
H14A−0.3146−0.7240−0.00200.071*
C15A−0.4803 (5)−0.6641 (10)0.00723 (13)0.0683 (16)
H15A−0.4958−0.77400.02300.082*
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)
H10−0.75800.2719−0.47880.080*
C2C−0.6432 (4)0.1384 (9)−0.44859 (13)0.0594 (14)
H11−0.57710.2238−0.45290.071*
C3C−0.6563 (4)−0.0432 (10)−0.42592 (15)0.0525 (14)
H12−0.6004−0.1010−0.41250.063*
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)
H13−0.8641−0.4157−0.42450.058*
C6C−0.8220 (4)−0.5912 (10)−0.37114 (13)0.0545 (13)
H14−0.7716−0.6637−0.35590.065*
H15−0.8473−0.7156−0.38540.065*
C7C−0.9949 (3)−0.3431 (8)−0.37802 (11)0.0492 (13)
H16−1.0294−0.4539−0.39270.059*
H17−1.0553−0.2570−0.36740.059*
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)
H18−0.8349−0.4075−0.31380.058*
H19−0.8434−0.1839−0.33600.058*
C10C−0.9987 (4)−0.6797 (8)−0.33978 (13)0.0540 (13)
H10C−1.0306−0.7793−0.35620.065*
H10D−0.9520−0.7800−0.32640.065*
C11C−1.0466 (4)−0.4235 (10)−0.29762 (12)0.0445 (11)
H11B−1.0004−0.5173−0.28300.053*
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−1.17400.0319−0.29460.070*
C14C−1.2866 (4)−0.1037 (14)−0.26034 (13)0.0701 (15)
H14C−1.33700.0201−0.25590.084*
C15C−1.2864 (4)−0.3213 (13)−0.24756 (13)0.0708 (17)
H15B−1.3377−0.3731−0.23240.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.056 (2)0.081 (3)0.055 (3)−0.0011 (19)−0.010 (2)0.012 (2)
O2A0.0440 (17)0.049 (2)0.0598 (19)0.0066 (15)−0.0060 (16)−0.0094 (16)
O3A0.0468 (18)0.047 (2)0.055 (2)0.0073 (16)−0.0066 (17)−0.002 (2)
O4A0.0347 (16)0.053 (2)0.063 (2)−0.0062 (14)−0.0055 (16)0.007 (2)
O5A0.0325 (16)0.052 (2)0.0610 (18)−0.0038 (13)−0.0051 (15)0.0122 (16)
O6A0.045 (2)0.091 (4)0.070 (3)0.0075 (18)0.005 (2)0.032 (2)
C1A0.050 (3)0.104 (6)0.056 (4)−0.002 (3)−0.012 (3)−0.006 (3)
C2A0.059 (4)0.077 (5)0.083 (4)−0.010 (3)−0.010 (3)−0.020 (4)
C3A0.058 (3)0.062 (4)0.062 (3)−0.007 (3)−0.011 (3)−0.004 (3)
C4A0.043 (3)0.058 (4)0.047 (3)0.002 (2)−0.005 (2)0.002 (2)
C5A0.043 (3)0.051 (3)0.053 (3)0.004 (2)0.003 (2)0.006 (3)
C6A0.038 (3)0.059 (3)0.052 (3)0.003 (2)0.002 (2)0.004 (2)
C7A0.053 (3)0.046 (3)0.060 (3)−0.003 (2)−0.015 (3)−0.002 (3)
C8A0.032 (2)0.040 (4)0.050 (4)0.0023 (18)−0.004 (2)−0.001 (2)
C9A0.053 (3)0.043 (3)0.073 (4)−0.006 (2)−0.015 (3)0.000 (3)
C10A0.034 (2)0.053 (3)0.057 (3)0.009 (2)−0.007 (2)0.005 (2)
C11A0.042 (3)0.052 (3)0.046 (3)0.000 (2)−0.005 (2)−0.001 (2)
C12A0.036 (2)0.053 (3)0.040 (3)−0.002 (2)0.001 (2)0.000 (2)
C13A0.045 (3)0.062 (4)0.063 (4)0.004 (2)0.010 (3)0.010 (3)
C14A0.052 (3)0.065 (4)0.061 (4)0.008 (2)−0.014 (3)0.002 (3)
C15A0.058 (3)0.081 (4)0.066 (4)−0.002 (3)−0.007 (3)0.025 (3)
O1C0.0427 (19)0.092 (4)0.076 (3)0.0014 (17)−0.001 (2)0.032 (2)
O2C0.0375 (16)0.052 (2)0.062 (2)0.0069 (15)0.0041 (17)0.008 (2)
O3C0.0334 (16)0.053 (2)0.0553 (18)0.0017 (14)0.0044 (14)0.0040 (16)
O4C0.0429 (18)0.051 (2)0.062 (2)−0.0053 (15)0.0059 (16)−0.0054 (17)
O5C0.0437 (18)0.0462 (19)0.057 (2)−0.0067 (16)0.0043 (17)−0.001 (2)
O6C0.061 (2)0.074 (3)0.056 (3)−0.0053 (18)0.009 (2)0.007 (2)
C1C0.058 (3)0.076 (4)0.068 (3)−0.001 (3)0.012 (3)0.032 (3)
C2C0.052 (3)0.062 (4)0.064 (4)−0.011 (2)−0.001 (3)0.004 (3)
C3C0.041 (3)0.065 (4)0.051 (4)−0.005 (2)0.000 (3)0.003 (3)
C4C0.040 (3)0.054 (3)0.046 (3)−0.001 (2)0.001 (2)0.002 (3)
C5C0.037 (2)0.051 (3)0.058 (3)0.003 (2)0.004 (2)−0.004 (2)
C6C0.048 (3)0.050 (3)0.066 (3)0.006 (2)0.012 (3)0.008 (3)
C7C0.035 (2)0.053 (3)0.060 (3)−0.003 (2)−0.002 (2)0.002 (2)
C8C0.042 (3)0.034 (3)0.058 (4)−0.0001 (18)0.001 (3)0.001 (2)
C9C0.031 (2)0.058 (3)0.057 (3)−0.002 (2)0.004 (2)−0.005 (2)
C10C0.057 (3)0.042 (3)0.063 (3)−0.004 (2)0.012 (3)0.000 (3)
C11C0.044 (3)0.048 (3)0.042 (3)0.002 (2)−0.002 (2)0.006 (3)
C12C0.047 (3)0.067 (4)0.036 (3)−0.005 (2)−0.003 (2)0.005 (2)
C13C0.058 (3)0.064 (4)0.055 (3)0.013 (3)0.007 (3)0.005 (3)
C14C0.055 (3)0.095 (5)0.060 (4)0.014 (3)0.005 (3)−0.011 (4)
C15C0.048 (3)0.106 (5)0.059 (3)−0.006 (3)0.015 (3)−0.011 (4)
Geometric parameters (Å, °) top
O1A—C4A1.370 (6)O1C—C4C1.363 (6)
O1A—C1A1.374 (7)O1C—C1C1.383 (6)
O2A—C5A1.401 (6)O2C—C5C1.401 (5)
O2A—C6A1.448 (5)O2C—C6C1.439 (6)
O3A—C5A1.416 (6)O3C—C5C1.418 (5)
O3A—C7A1.445 (5)O3C—C7C1.442 (5)
O4A—C11A1.405 (5)O4C—C11C1.410 (6)
O4A—C9A1.448 (6)O4C—C9C1.439 (5)
O5A—C11A1.412 (5)O5C—C11C1.417 (6)
O5A—C10A1.430 (5)O5C—C10C1.440 (6)
O6A—C15A1.363 (6)O6C—C15C1.377 (7)
O6A—C12A1.375 (6)O6C—C12C1.377 (6)
C1A—C2A1.327 (9)C1C—C2C1.327 (7)
C1A—H10.9300C1C—H100.9300
C2A—C3A1.431 (7)C2C—C3C1.411 (8)
C2A—H20.9300C2C—H110.9300
C3A—C4A1.324 (7)C3C—C4C1.343 (6)
C3A—H3A0.9300C3C—H120.9300
C4A—C5A1.486 (6)C4C—C5C1.491 (6)
C5A—H30.9800C5C—H130.9800
C6A—C8A1.512 (8)C6C—C8C1.545 (7)
C6A—H40.9700C6C—H140.9700
C6A—H50.9700C6C—H150.9700
C7A—C8A1.526 (7)C7C—C8C1.512 (7)
C7A—H60.9700C7C—H160.9700
C7A—H70.9700C7C—H170.9700
C8A—C9A1.528 (7)C8C—C10C1.531 (7)
C8A—C10A1.532 (7)C8C—C9C1.536 (8)
C9A—H80.9700C9C—H180.9700
C9A—H90.9700C9C—H190.9700
C10A—H10A0.9700C10C—H10C0.9700
C10A—H10B0.9700C10C—H10D0.9700
C11A—C12A1.484 (6)C11C—C12C1.487 (7)
C11A—H11A0.9800C11C—H11B0.9800
C12A—C13A1.328 (6)C12C—C13C1.352 (7)
C13A—C14A1.427 (8)C13C—C14C1.420 (7)
C13A—H13A0.9300C13C—H13B0.9300
C14A—C15A1.315 (6)C14C—C15C1.332 (8)
C14A—H14A0.9300C14C—H14C0.9300
C15A—H15A0.9300C15C—H15B0.9300
C4A—O1A—C1A105.7 (5)C4C—O1C—C1C105.7 (4)
C5A—O2A—C6A111.5 (4)C5C—O2C—C6C110.7 (3)
C5A—O3A—C7A110.7 (3)C5C—O3C—C7C110.6 (3)
C11A—O4A—C9A110.7 (3)C11C—O4C—C9C111.8 (4)
C11A—O5A—C10A110.5 (3)C11C—O5C—C10C112.0 (3)
C15A—O6A—C12A106.0 (4)C15C—O6C—C12C105.5 (5)
C2A—C1A—O1A110.7 (5)C2C—C1C—O1C110.2 (5)
C2A—C1A—H1124.7C2C—C1C—H10124.9
O1A—C1A—H1124.7O1C—C1C—H10124.9
C1A—C2A—C3A106.2 (6)C1C—C2C—C3C107.0 (4)
C1A—C2A—H2126.9C1C—C2C—H11126.5
C3A—C2A—H2126.9C3C—C2C—H11126.5
C4A—C3A—C2A106.9 (6)C4C—C3C—C2C106.9 (5)
C4A—C3A—H3A126.5C4C—C3C—H12126.6
C2A—C3A—H3A126.5C2C—C3C—H12126.6
C3A—C4A—O1A110.5 (4)C3C—C4C—O1C110.2 (5)
C3A—C4A—C5A133.5 (5)C3C—C4C—C5C134.0 (5)
O1A—C4A—C5A116.0 (5)O1C—C4C—C5C115.8 (4)
O2A—C5A—O3A112.1 (4)O2C—C5C—O3C111.8 (4)
O2A—C5A—C4A107.0 (4)O2C—C5C—C4C108.0 (4)
O3A—C5A—C4A108.0 (3)O3C—C5C—C4C108.2 (4)
O2A—C5A—H3109.9O2C—C5C—H13109.6
O3A—C5A—H3109.9O3C—C5C—H13109.6
C4A—C5A—H3109.9C4C—C5C—H13109.6
O2A—C6A—C8A111.3 (3)O2C—C6C—C8C110.6 (4)
O2A—C6A—H4109.4O2C—C6C—H14109.5
C8A—C6A—H4109.4C8C—C6C—H14109.5
O2A—C6A—H5109.4O2C—C6C—H15109.5
C8A—C6A—H5109.4C8C—C6C—H15109.5
H4—C6A—H5108.0H14—C6C—H15108.1
O3A—C7A—C8A110.3 (4)O3C—C7C—C8C110.8 (3)
O3A—C7A—H6109.6O3C—C7C—H16109.5
C8A—C7A—H6109.6C8C—C7C—H16109.5
O3A—C7A—H7109.6O3C—C7C—H17109.5
C8A—C7A—H7109.6C8C—C7C—H17109.5
H6—C7A—H7108.1H16—C7C—H17108.1
C6A—C8A—C9A110.8 (4)C7C—C8C—C10C109.9 (4)
C6A—C8A—C7A107.1 (5)C7C—C8C—C9C111.4 (4)
C9A—C8A—C7A110.0 (4)C10C—C8C—C9C107.5 (5)
C6A—C8A—C10A110.9 (4)C7C—C8C—C6C108.3 (5)
C9A—C8A—C10A107.7 (5)C10C—C8C—C6C110.1 (4)
C7A—C8A—C10A110.2 (4)C9C—C8C—C6C109.7 (4)
O4A—C9A—C8A110.2 (4)O4C—C9C—C8C109.7 (3)
O4A—C9A—H8109.6O4C—C9C—H18109.7
C8A—C9A—H8109.6C8C—C9C—H18109.7
O4A—C9A—H9109.6O4C—C9C—H19109.7
C8A—C9A—H9109.6C8C—C9C—H19109.7
H8—C9A—H9108.1H18—C9C—H19108.2
O5A—C10A—C8A110.4 (3)O5C—C10C—C8C109.3 (4)
O5A—C10A—H10A109.6O5C—C10C—H10C109.8
C8A—C10A—H10A109.6C8C—C10C—H10C109.8
O5A—C10A—H10B109.6O5C—C10C—H10D109.8
C8A—C10A—H10B109.6C8C—C10C—H10D109.8
H10A—C10A—H10B108.1H10C—C10C—H10D108.3
O4A—C11A—O5A110.9 (4)O4C—C11C—O5C111.2 (4)
O4A—C11A—C12A107.2 (3)O4C—C11C—C12C106.9 (4)
O5A—C11A—C12A108.7 (4)O5C—C11C—C12C108.7 (4)
O4A—C11A—H11A110.0O4C—C11C—H11B110.0
O5A—C11A—H11A110.0O5C—C11C—H11B110.0
C12A—C11A—H11A110.0C12C—C11C—H11B110.0
C13A—C12A—O6A109.6 (5)C13C—C12C—O6C110.1 (5)
C13A—C12A—C11A134.8 (5)C13C—C12C—C11C133.7 (5)
O6A—C12A—C11A115.6 (4)O6C—C12C—C11C116.2 (5)
C12A—C13A—C14A107.0 (5)C12C—C13C—C14C106.5 (6)
C12A—C13A—H13A126.5C12C—C13C—H13B126.7
C14A—C13A—H13A126.5C14C—C13C—H13B126.7
C15A—C14A—C13A106.4 (5)C15C—C14C—C13C106.9 (6)
C15A—C14A—H14A126.8C15C—C14C—H14C126.6
C13A—C14A—H14A126.8C13C—C14C—H14C126.6
C14A—C15A—O6A111.0 (5)C14C—C15C—O6C110.9 (5)
C14A—C15A—H15A124.5C14C—C15C—H15B124.5
O6A—C15A—H15A124.5O6C—C15C—H15B124.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1A—H1···Cg10.932.703.478 (6)142
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1A—H1···Cg10.932.703.478 (6)142
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Jermy, B. R. & Pandurangan, A. (2005). Appl. Catal. A, 295, 185–192.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.