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The crystal structure of benzoylacetone (1-phenyl-1,3-butanedione, C10H10O2; P21/c, Z = 4) has been determined at 300, 160 (both Mo Kα X-ray diffraction, XRD), 20 (λ = 1.012 Å neutron diffraction, ND) and 8 K (Ag Kα XRD), to which should be added earlier structure determinations at 300 (Mo Kα XRD and ND, λ = 0.983 Å) and 143 K (Mo Kα XRD). Cell dimensions have been measured over the temperature range 8–­300 K; a first- or second-order phase change does not occur within this range. The atomic displacement parameters have been analyzed using the thermal motion analysis program THMA11. The most marked change in the molecular structure is in the disposition of the methyl group, which has a librational amplitude of ∼20° at 20 K and is rotationally disordered at 300 K. The lengths of the two C—O bonds in the cis-enol ring do not differ significantly, nor do those of the two C—C bonds, nor do these lengths change between 8 and 300 K. An ND difference synthesis (20 K) shows a single enol hydrogen trough (rather than two half H atoms), approximately centered between the O atoms; analogous results were obtained by XRD (8 K). It is inferred that the enol hydrogen is in a broad, flat-bottomed single-minimum potential well between the O atoms, with a libration amplitude of ∼0.30 Å at 8 K. These results suggest that at 8 K the cis-enol ring in benzoylacetone has quasi-aromatic character, in agreement with the results of high-level ab initio calculations made for benzoylacetone [Schiøtt et al. (1998). J. Am. Chem. Soc. 120, 12117–12124]. Application [in a related paper by Madsen et al. (1998). J. Am. Chem. Soc. 120, 10040–10045] of multipolar analysis and topological methods to the charge density obtained from the combined lowest temperature X-ray and neutron data provides evidence for an intramolecular hydrogen bond with partly electrostatic and partly covalent character, and large p-delocalization in the cis-enol ring. This is in good agreement with what is expected from the observed bond lengths. Analysis of the total available (through the Cambridge Structural Database, CSD) population of cis-enol ring geometries confirms earlier reports of correlation between the degree of bond localization in the pairs of C—C and C—O bonds, but does not show the dependence of bond localization on d(O...O) that was reported earlier for a more restricted sample. It is suggested that the only reliable method of determining whether the enol hydrogen is found in a single or double potential well is by low-temperature X-­ray or (preferably) neutron diffraction.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, xray, neutron

hkl

Structure factor file (CIF format)
Contains datablock benzoylacetone

hkl

Structure factor file (CIF format)
Contains datablock benzoylacetone

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Supplementary material

CCDC references: 136457; 136458

Computing details top

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(xray) top
Crystal data top
C10H10O2Dx = 1.350 Mg m3
Mr = 162.19Ag Kα radiation, λ = 0.5616 Å
Monoclinic, P21/CCell parameters from 91 reflections
a = 8.006 (3) Åθ = 13.6–22.8°
b = 5.482 (3) ŵ = 0.06 mm1
c = 19.444 (8) ÅT = 20 K
β = 110.46 (3)°Spherical, colourless
V = 799.5 (5) Å30.3 mm (radius)
Z = 4
Data collection top
Huber 512
diffractometer
Rint = 0.024
2θ/ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: gaussian
?
h = 912
Tmin = 0.972, Tmax = 0.973k = 88
10494 measured reflectionsl = 2926
2862 independent reflections3 standard reflections every 50 reflections
2013 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-atom parameters not refined
Least-squares matrix: fullCalculated w = 1/[σ2]
R[F2 > 2σ(F2)] = 0.026(Δ/σ)max = 0.06
wR(F2) = 0.0231Δρmax = 0.15 e Å3
2013 reflectionsΔρmin = 0.13 e Å3
307 parameters
Crystal data top
C10H10O2V = 799.5 (5) Å3
Mr = 162.19Z = 4
Monoclinic, P21/CAg Kα radiation, λ = 0.5616 Å
a = 8.006 (3) ŵ = 0.06 mm1
b = 5.482 (3) ÅT = 20 K
c = 19.444 (8) Å0.3 mm (radius)
β = 110.46 (3)°
Data collection top
Huber 512
diffractometer
2013 reflections with I > 2σ(I)
Absorption correction: gaussian
?
Rint = 0.024
Tmin = 0.972, Tmax = 0.9733 standard reflections every 50 reflections
10494 measured reflections intensity decay: none
2862 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters not refined
wR(F2) = 0.0231Δρmax = 0.15 e Å3
2013 reflectionsΔρmin = 0.13 e Å3
307 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(1)0.2432 (2)0.3076 (3)0.04171 (8)0.010
O(2)0.4922 (2)0.1317 (3)0.06367 (8)0.009
C(1)0.1234 (2)0.7008 (2)0.03634 (6)0.010
C(2)0.2507 (2)0.4985 (2)0.00234 (6)0.008
C(3)0.3740 (2)0.5199 (2)0.06969 (6)0.008
C(4)0.4924 (1)0.3281 (2)0.10055 (6)0.007
C(5)0.6223 (1)0.3358 (2)0.17655 (6)0.006
C(6)0.6232 (1)0.5266 (2)0.22471 (5)0.007
C(7)0.7462 (1)0.5262 (2)0.29599 (5)0.008
C(8)0.8693 (2)0.3368 (2)0.32015 (6)0.008
C(9)0.8688 (1)0.1466 (2)0.27246 (5)0.008
C(10)0.7455 (1)0.1444 (2)0.20119 (5)0.008
H(1A)0.10430.82110.00300.052
H(1B)0.00300.63010.06940.039
H(1C)0.17190.80550.07050.059
H(3)0.37820.68710.09920.021
H(6)0.52820.67380.20730.019
H(7)0.74530.67510.33280.020
H(8)0.96660.33720.37550.019
H(9)0.96580.00130.29060.020
H(10)0.74360.00340.16410.020
H(X1)0.37650.17680.00280.048
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.0114 (4)0.0086 (5)0.0065 (4)0.0007 (5)0.0003 (4)0.0005 (3)
O(2)0.0075 (5)0.0107 (5)0.0079 (5)0.0013 (5)0.0001 (4)0.0031 (5)
C(1)0.0090 (5)0.0101 (5)0.0099 (4)0.0016 (5)0.0014 (4)0.0019 (4)
C(2)0.0070 (5)0.0096 (5)0.0069 (5)0.0015 (5)0.0018 (4)0.0004 (5)
C(3)0.0085 (5)0.0075 (5)0.0072 (5)0.0024 (4)0.0009 (4)0.0013 (4)
C(4)0.0066 (5)0.0072 (5)0.0053 (4)0.0000 (4)0.0002 (4)0.0006 (4)
C(5)0.0066 (4)0.0055 (5)0.0059 (4)0.0010 (4)0.0008 (4)0.0001 (4)
C(6)0.0080 (4)0.0068 (4)0.0058 (4)0.0008 (3)0.0006 (3)0.0012 (3)
C(7)0.0084 (4)0.0083 (4)0.0069 (4)0.0008 (4)0.0013 (3)0.0013 (3)
C(8)0.0079 (5)0.0092 (5)0.0060 (4)0.0011 (4)0.0010 (4)0.0000 (4)
C(9)0.0083 (4)0.0064 (4)0.0071 (4)0.0020 (3)0.0007 (3)0.0005 (3)
C(10)0.0085 (4)0.0062 (4)0.0063 (4)0.0015 (4)0.0010 (3)0.0003 (3)
Geometric parameters (Å, º) top
O(1)—O(2)2.499 (2)C(4)—C(5)1.481 (1)
C(2)—O(1)1.286 (2)C(5)—C(6)1.402 (1)
C(4)—O(2)1.293 (2)C(5)—C(10)1.405 (1)
O(1)—H(X1)1.325C(6)—C(7)1.391 (1)
O(2)—H(X1)1.247C(7)—C(8)1.395 (2)
C(1)—C(2)1.495 (2)C(8)—C(9)1.395 (2)
C(1)—H(1A)1.060C(9)—C(10)1.392 (1)
C(1)—H(1B)1.064C(6)—H(6)1.079
C(1)—H(1C)1.050C(7)—H(7)1.087
C(2)—C(3)1.408 (2)C(8)—H(8)1.086
C(3)—C(4)1.402 (2)C(9)—H(9)1.092
C(3)—H(3)1.076C(10)—H(10)1.081
C(2)—O(1)—H(X1)101.1C(4)—C(5)—C(6)121.7 (1)
C(4)—O(2)—H(X1)102.6C(4)—C(5)—C(10)118.9 (1)
O(1)—H(X1)—O(2)152.7C(6)—C(5)—C(10)119.4 (2)
C(2)—C(1)—H(1A)113.0C(5)—C(6)—C(7)120.0 (1)
C(2)—C(1)—H(1B)110.7C(5)—C(6)—H(6)120.6
C(2)—C(1)—H(1C)109.8C(7)—C(6)—H(6)119.3
H(1A)—C(1)—H(1B)108.4C(6)—C(7)—C(8)120.5 (1)
H(1A)—C(1)—H(1C)107.2C(6)—C(7)—H(7)119.3
H(1B)—C(1)—H(1C)107.5C(8)—C(7)—H(7)120.2
O(1)—C(2)—C(1)117.3 (2)C(7)—C(8)—C(9)119.7 (2)
O(1)—C(2)—C(3)122.0 (2)C(7)—C(8)—H(8)120.7
C(1)—C(2)—C(3)120.7 (2)C(9)—C(8)—H(8)119.6
C(2)—C(3)—C(4)119.8 (2)C(8)—C(9)—C(10)120.3 (1)
C(2)—C(3)—H(3)118.8C(8)—C(9)—H(9)120.2 (1)
C(4)—C(3)—H(3)121.3C(10)—C(9)—H(9)119.5
O(2)—C(4)—C(3)121.2 (2)C(5)—C(10)—C(9)120.1 (1)
O(2)—C(4)—C(5)116.2 (2)C(5)—C(10)—H(10)119.2
C(3)—C(4)—C(5)122.7 (2)C(9)—C(10)—H(10)120.7
(neutron) top
Crystal data top
C10H10O2Dx = 1.350 Mg m3
Mr = 162.19Neutron radiation, λ = 1.012 Å
Monoclinic, P21/CCell parameters from 50 reflections
a = 8.027 (7) Åθ = 8.1–43.8°
b = 5.483 (2) ŵ = 0.20 mm1
c = 19.478 (13) ÅT = 20 K
β = 110.42 (5)°Prism, colourless
V = 803.4 (6) Å36.0 × 2.8 × 1.2 mm
Z = 4
Data collection top
Huber 512
diffractometer
Rint = 0.023
Berylium monochromatorθmax = 45.2°, θmin = 3.2°
2θ/ω scansh = 1110
Absorption correction: gaussian
?
k = 17
Tmin = 0.555, Tmax = 0.737l = 627
2722 measured reflections3 standard reflections every 60 reflections
1597 independent reflections intensity decay: none
1236 reflections with I > 2σ(I)
Refinement top
Refinement on F2Calculated w = 1/[σ2]
Least-squares matrix: full(Δ/σ)max = 0.01
R[F2 > 2σ(F2)] = 0.052Δρmax = 0.04 e Å3
wR(F2) = 0.0500Δρmin = 0.04 e Å3
1236 reflectionsExtinction correction: XD
219 parametersExtinction coefficient: 0.102 (4)
All H-atom parameters refined
Crystal data top
C10H10O2V = 803.4 (6) Å3
Mr = 162.19Z = 4
Monoclinic, P21/CNeutron radiation, λ = 1.012 Å
a = 8.027 (7) ŵ = 0.20 mm1
b = 5.483 (2) ÅT = 20 K
c = 19.478 (13) Å6.0 × 2.8 × 1.2 mm
β = 110.42 (5)°
Data collection top
Huber 512
diffractometer
1236 reflections with I > 2σ(I)
Absorption correction: gaussian
?
Rint = 0.023
Tmin = 0.555, Tmax = 0.7373 standard reflections every 60 reflections
2722 measured reflections intensity decay: none
1597 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052All H-atom parameters refined
wR(F2) = 0.0500Δρmax = 0.04 e Å3
1236 reflectionsΔρmin = 0.04 e Å3
219 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(1)0.2431 (4)0.3084 (5)0.0416 (1)0.013
O(2)0.4920 (4)0.1328 (5)0.0635 (2)0.013
C(1)0.1230 (3)0.7009 (4)0.0365 (1)0.013
C(2)0.2508 (3)0.4990 (4)0.0023 (1)0.010
C(3)0.3743 (3)0.5201 (4)0.0698 (1)0.010
C(4)0.4923 (3)0.3278 (4)0.1007 (1)0.009
C(5)0.6226 (3)0.3355 (4)0.1765 (1)0.009
C(6)0.6231 (3)0.5268 (4)0.2245 (1)0.010
C(7)0.7466 (3)0.5258 (4)0.2962 (1)0.011
C(8)0.8688 (3)0.3375 (4)0.3200 (1)0.010
C(9)0.8690 (3)0.1459 (4)0.2724 (1)0.011
C(10)0.7455 (3)0.1444 (4)0.2012 (1)0.010
H(1A)0.1043 (11)0.8211 (14)0.0030 (4)0.068
H(1B)0.0030 (9)0.6301 (12)0.0694 (4)0.052
H(1C)0.1719 (9)0.8054 (13)0.0705 (5)0.078
H(3)0.3782 (7)0.6871 (10)0.0992 (3)0.028
H(6)0.5282 (7)0.6738 (9)0.2073 (3)0.025
H(7)0.7453 (7)0.6751 (9)0.3328 (3)0.026
H(8)0.9666 (7)0.3372 (10)0.3755 (3)0.024
H(9)0.9658 (7)0.0013 (9)0.2906 (3)0.027
H(10)0.7436 (7)0.0034 (10)0.1641 (3)0.027
H(X1)0.3764 (19)0.177 (3)0.0027 (8)0.063
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.012 (1)0.013 (1)0.010 (1)0.002 (1)0.001 (1)0.002 (1)
O(2)0.015 (1)0.010 (1)0.011 (2)0.000 (1)0.002 (1)0.003 (1)
C(1)0.013 (1)0.009 (1)0.013 (1)0.001 (1)0.002 (1)0.001 (1)
C(2)0.011 (1)0.009 (1)0.009 (1)0.002 (1)0.002 (1)0.001 (1)
C(3)0.013 (1)0.008 (1)0.007 (1)0.003 (1)0.000 (1)0.001 (1)
C(4)0.011 (1)0.006 (1)0.009 (1)0.000 (1)0.001 (1)0.000 (1)
C(5)0.012 (1)0.006 (1)0.007 (1)0.000 (1)0.002 (1)0.000 (1)
C(6)0.012 (1)0.007 (1)0.010 (1)0.001 (1)0.001 (1)0.001 (1)
C(7)0.012 (1)0.010 (1)0.008 (1)0.003 (1)0.002 (1)0.001 (1)
C(8)0.010 (1)0.008 (1)0.008 (1)0.002 (1)0.000 (1)0.001 (1)
C(9)0.012 (1)0.009 (1)0.010 (1)0.002 (1)0.002 (1)0.000 (1)
C(10)0.012 (1)0.008 (1)0.009 (1)0.001 (1)0.001 (1)0.000 (1)
H(1A)0.091 (6)0.065 (5)0.030 (3)0.051 (5)0.001 (4)0.017 (4)
H(1B)0.030 (3)0.029 (4)0.077 (5)0.005 (3)0.015 (4)0.002 (4)
H(1C)0.061 (4)0.054 (4)0.117 (7)0.036 (4)0.060 (5)0.068 (5)
H(3)0.037 (3)0.016 (2)0.023 (3)0.006 (2)0.002 (3)0.006 (2)
H(6)0.029 (3)0.018 (2)0.023 (3)0.012 (2)0.003 (2)0.001 (2)
H(7)0.031 (3)0.019 (2)0.021 (3)0.003 (2)0.001 (2)0.008 (2)
H(8)0.027 (3)0.031 (3)0.008 (3)0.005 (2)0.006 (3)0.002 (2)
H(9)0.028 (3)0.023 (2)0.022 (3)0.013 (2)0.000 (2)0.008 (2)
H(10)0.030 (3)0.024 (3)0.019 (3)0.005 (2)0.000 (3)0.006 (2)
H(X1)0.066 (6)0.047 (4)0.077 (6)0.022 (4)0.053 (6)0.025 (4)
Geometric parameters (Å, º) top
O(1)—O(2)2.502 (4)C(4)—C(5)1.483 (4)
C(2)—O(1)1.286 (4)C(5)—C(6)1.406 (3)
C(4)—O(2)1.293 (4)C(5)—C(10)1.404 (3)
O(1)—H(X1)1.329 (11)C(6)—C(7)1.402 (4)
O(2)—H(X1)1.245 (11)C(7)—C(8)1.387 (4)
C(1)—C(2)1.499 (4)C(8)—C(9)1.404 (4)
C(1)—H(1A)1.064 (7)C(9)—C(10)1.394 (4)
C(1)—H(1B)1.062 (8)C(6)—H(6)1.079 (6)
C(1)—H(1C)1.051 (6)C(7)—H(7)1.090 (6)
C(2)—C(3)1.414 (4)C(8)—H(8)1.091 (7)
C(3)—C(4)1.405 (4)C(9)—H(9)1.090 (6)
C(3)—H(3)1.076 (6)C(10)—H(10)1.085 (6)
C(2)—O(1)—H(X1)101.2 (4)C(4)—C(5)—C(6)121.5 (2)
C(4)—O(2)—H(X1)103.2 (4)C(4)—C(5)—C(10)119.0 (2)
O(1)—H(X1)—O(2)152.3 (6)C(6)—C(5)—C(10)119.5 (3)
C(2)—C(1)—H(1A)112.6 (5)C(5)—C(6)—C(7)119.8 (3)
C(2)—C(1)—H(1B)110.8 (4)C(5)—C(6)—H(6)120.9 (4)
C(2)—C(1)—H(1C)109.8 (4)C(7)—C(6)—H(6)119.2 (4)
H(1A)—C(1)—H(1B)108.7 (7)C(6)—C(7)—C(8)120.4 (3)
H(1A)—C(1)—H(1C)107.2 (7)C(6)—C(7)—H(7)119.0 (4)
H(1B)—C(1)—H(1C)107.7 (7)C(8)—C(7)—H(7)120.6 (4)
O(1)—C(2)—C(1)117.0 (3)C(7)—C(8)—C(9)120.1 (3)
O(1)—C(2)—C(3)122.1 (3)C(7)—C(8)—H(8)120.7 (4)
C(1)—C(2)—C(3)120.9 (2)C(9)—C(8)—H(8)119.2 (4)
C(2)—C(3)—C(4)119.7 (2)C(8)—C(9)—C(10)119.9 (3)
C(2)—C(3)—H(3)118.7 (4)C(8)—C(9)—H(9)120.4 (4)
C(4)—C(3)—H(3)121.5 (4)C(10)—C(9)—H(9)119.7 (4)
O(2)—C(4)—C(3)120.9 (3)C(5)—C(10)—C(9)120.3 (2)
O(2)—C(4)—C(5)116.4 (3)C(5)—C(10)—H(10)119.1 (4)
C(3)—C(4)—C(5)122.6 (2)C(9)—C(10)—H(10)120.6 (4)

Experimental details

(xray)(neutron)
Crystal data
Chemical formulaC10H10O2C10H10O2
Mr162.19162.19
Crystal system, space groupMonoclinic, P21/CMonoclinic, P21/C
Temperature (K)2020
a, b, c (Å)8.006 (3), 5.482 (3), 19.444 (8)8.027 (7), 5.483 (2), 19.478 (13)
β (°) 110.46 (3) 110.42 (5)
V3)799.5 (5)803.4 (6)
Z44
Radiation typeAg Kα, λ = 0.5616 ÅNeutron, λ = 1.012 Å
µ (mm1)0.060.20
Crystal size (mm)0.3 (radius)6.0 × 2.8 × 1.2
Data collection
DiffractometerHuber 512
diffractometer
Huber 512
diffractometer
Absorption correctionGaussianGaussian
Tmin, Tmax0.972, 0.9730.555, 0.737
No. of measured, independent and
observed [I > 2σ(I)] reflections
10494, 2862, 2013 2722, 1597, 1236
Rint0.0240.023
(sin θ/λ)max1)0.7530.701
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.0231, ? 0.052, 0.0500, ?
No. of reflections20131236
No. of parameters307219
No. of restraints??
H-atom treatmentH-atom parameters not refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.15, 0.130.04, 0.04

Table 10. Benzoylacetone - molecular dimensions, bonds (Å) and angles (°)). top
(a) Interatomic distances determined in the 20 K ND and the 8.4K XRD studies. The small differences between ND and XRD X-H distances are due to the use of fixed ND parameters for hydrogens in the X-ray refinement; thus s.u.'s are omitted for XRD distances involving hydrogen. (b) Bond angles determined in the 20K ND and the 8.4K XRD studies. As the hydrogen parameters were not refined in the X-ray study, s.u.'s are omitted for anglews involving hydrogen.
O(1)—O(2)2.502 (4)2.499 (2)
C(2)—O(1)1.286 (4)1.286 (2)
C(4)—O(2)1.293 (4)1.293 (2)
O(1)—H(X1)1.329 (11)1.325
O(2)—H(X1)1.245 (11)1.247
C(1)—C(2)1.499 (4)1.495 (2)
C(1)—H(1A)1.064 (7)1.060
C(1)—H(1B)1.062 (8)1.064
C(1)—H(1C)1.051 (6)1.050
C(2)—C(3)1.414 (4)1.408 (2)
C(3)—C(4)1.405 (4)1.402 (2)
C(3)—H(3)1.076 (6)1.076
C(4)—C(5)1.483 (4)1.481 (1)
C(5)—C(6)1.406 (3)1.402 (1)
C(5)—C(10)1.404 (3)1.405 (1)
C(6)—C(7)1.402 (4)1.391 (1)
C(7)—C(8)1.387 (4)1.395 (2)
C(8)—C(9)1.404 (4)1.395 (2)
C(9)—C(10)1.394 (4)1.392 (1)
C(6)—H(6)1.079 (6)1.079
C(7)—H(7)1.090 (6)1.087
C(8)—H(8)1.091 (7)1.086
C(9)—H(9)1.090 (6)1.092
C(10)—H(10)1.085 (6)1.081
C(2)—O(1)—H(X1)101.2 (4)101.1
C(4)—O(2)—H(X1)103.2 (4)102.6
O(1)—H(X1)—O(2)152.3 (6)152.7
C(2)—C(1)—H(1A)112.6 (5)113.0
C(2)—C(1)—H(1B)110.8 (4)110.7
C(2)—C(1)—H(1C)109.8 (4)109.8
H(1A)—C(1)—H(1B)108.7 (7)108.4
H(1A)—C(1)—H(1C)107.2 (7)107.2
H(1B)—C(1)—H(1C)107.7 (7)107.5
O(1)—C(2)—C(1)117.0 (3)117.3 (2)
O(1)—C(2)—C(3)122.1 (3)122.0 (2)
C(1)—C(2)—C(3)120.9 (2)120.7 (2)
C(2)—C(3)—C(4)119.7 (2)119.8 (2)
C(2)—C(3)—H(3)118.7 (4)118.8
C(4)—C(3)—H(3)121.5 (4)121.3
O(2)—C(4)—C(3)120.9 (3)121.2 (2)
O(2)—C(4)—C(5)116.4 (3)116.2 (2)
C(3)—C(4)—C(5)122.6 (2)122.7 (2)
C(4)—C(5)—C(6)121.5 (2)121.7 (1)
C(4)—C(5)—C(10)119.0 (2)118.9 (1)
C(6)—C(5)—C(10)119.5 (3)119.4 (2)
C(5)—C(6)—C(7)119.8 (3)120.0 (1)
C(5)—C(6)—H(6)120.9 (4)120.6
C(7)—C(6)—H(6)119.2 (4)119.3
C(6)—C(7)—C(8)120.4 (3)120.5 (1)
C(6)—C(7)—H(7)119.0 (4)119.3
C(8)—C(7)—H(7)120.6 (4)120.2
C(7)—C(8)—C(9)120.1 (3)119.7 (2)
C(7)—C(8)—H(8)120.7 (4)120.7
C(9)—C(8)—H(8)119.2 (4)119.6
C(8)—C(9)—C(10)119.9 (3)120.3 (1)
C(8)—C(9)—H(9)120.4 (4)120.2 (1)
C(10)—C(9)—H(9)119.7 (4)119.5
C(5)—C(10)—C(9)120.3 (2)120.1 (1)
C(5)—C(10)—H(10)119.1 (4)119.2
C(9)—C(10)—H(10)120.6 (4)120.7
 
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