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The structure of bis­(4-tert-butyl-2,6-dimethyl­phenyl)hexa-1,5-diyne-3,4-dione, C30H34O2, has been determined, revealing an extended s-trans conformation of the dione and the two ynone moieties, which are shielded by the flanking methyl substituents. The structural parameters and the packing arrangement suggest little electronic delocalization between the two ynone moieties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105006426/fg1824sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105006426/fg1824Isup2.hkl
Contains datablock I

CCDC reference: 269051

Comment top

The title compound is a newly synthesized member of the diacetylenic 1,2-diones, a class of compounds first introduced in 1996 (Faust & Weber, 1996; Faust et al., 1997). The two typifying interconnected ynone moieties of this molecular structure give rise to a rich chemistry that we have explored to form, inter alia, metal-chelating diazabutadienes (Faust, Göbelt & Weber, 1999; Faust, Göbelt et al., 1999), alkyne-substituted N-heterocyclic carbenes (Faust & Göbelt, 2000) and acetylenic phthalocyanines (Faust, 2001). Despite these successful developments, two questions remain about the electronic aspects of these compounds. Firstly, the kinetic stability of dialkynyl diones appears to rely largely on the size of the terminal alkyne substituents. Whereas bulky triisoproylsilyl groups lend excellent stability to the hexadiynedione core, smaller terminal substituents, such as alkyls or the trimethylsilyl group, are insufficient to protect the reactive ynone system from nucleophilic attack (Faust et al., 1997). Similarly, aryl termini shield the reactive core of the molecule most effectively when, as in the case discussed here, they possess sizeable 2,6-substituents flanking the alkyne subunit. The second question concerns the effective conjugation path of the hexa-1,5-diyne-3,4-dione framework. We have speculated that, similar to the related 2,3-dialkynyldiazabutadienes (Faust et al., 1999 Which?), a valid description of dialkynyl diones is that of two interconnected but largely electronically independent bis(ynone) units, rather than that of a species fully delocalized along the hexadiynedione core. The present solid-state study is the first on this class of compounds and was undertaken to shed some light on these matters.

The title compound, (I), with the atomic numbering, is shown in Fig. 1. The molecule crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Inspection of Fig. 1 reveals an extended conformation of the molecule with a formal s-trans geometry [torsion angle O2—C4—C3—O1 175.2 (2) °] around the 1,2-dione subunit. The maximum deviation of the atoms from a plane through C2/C3/C4/C5/O1/O2 is only 0.062 (1) Å For which atom?. The phenyl ring system around C7 is almost perfectly coplanar with the dione unit, as the plane through C1/C2/C3/C7/C8/C12/O1 forms an angle of only 4.2 (1)° with that of the dione substructure. On the other hand, the phenyl ring system around C19 (i.e. a plane through C4/C5/C6/C19/C20/C24) is twisted by about 20.3 (1)° from the plane of the dione moiety.

In terms of π electronic delocalization, it appears that, in the crystal, the electronic interaction between one phenyl group and the ynone portion of the molecule is maximized, whereas that of the other is slightly diminished. The distance between the two carbonyl atoms C3—C4 is 1.535 (2) Å (Table 1), suggesting a rather long Csp2—Csp2 single bond through which little electron density is transmitted. While most other structural parameters within this part of the molecule are within the normal range (Allen et al., 1987), the C—C—C angles around the carbonyl C atoms [i.e. C2—C3—C4 116.7 (1)° and C3—C4—C5 114.5 (1)°] are significantly compressed.

The methyl groups on the 2,6-positions on the aryl rings protrude into the space segment above and below the C1C2 (and C5C6) triple bonds, a structural feature that helps to explain the increased stability of this system towards nucleophilic attack, particularly in solution, where there is free rotation around the C7—C1 (and C6—C19) single bonds. There are no close intramolecular contacts between the methyl H atoms and the carbonyl O atoms.

An inspection of the packing arrangement (Fig. 2) of compound (I) in the crystal reveals that the tert-butyl groups of one molecule reside in the space above the dione subunits of adjacent molecules. In conjunction with the findings above, this might indicate that the planarity of the dione substructure is dictated by the space requirements of the bulky alkyl group, rather than by intramolecular electronic interactions such as π delocalization. The crystal packing forces are enhanced by very weak intermolecular hydrogen bonds between methyl H atoms and the carbonyl O atoms. The relevant distances are depicted as dashed lines in Fig. 2, with details given in Table 2. In this way, chains of centrosymmetric rings develop along [101]. The alkyl substitution of the aryl rings prevents intermolecular ππ stacking interactions.

Experimental top

Compound (I) was synthesized from 4-tert-butyl-2,6-dimethylphenylacetylene and oxalyl chloride following the procedure outlined in Faust et al. (1997) [m.p. 437 K (decomposition)]. Spectroscopic analysis: IR (Medium?, ν, cm-1): 2953, 2176, 1664, 1107; 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 7.05 (4H, s, CH), 2.47 (12H, s, CH3), 1.28 (18H, s, CH3); 13C NMR (125.7 MHz, CDCl3, δ, p.p.m.): 173.31, 155.28, 143.79, 124.46, 116.32, 93.74, 80.99, 34.93, 30.98, 21.24; APCI-MS: 427 (33) [M+H]+; 399 (70) [M—CO+H]+; 213 (100) [M/2]+. Single crystals of (I) suitable for X-ray diffraction studies were obtained by slow evaporation from acetonitrile.

Refinement top

H atoms were placed in geometric positions and treated as riding, with C—H distances in the range 0.94–0.97 Å and with Uiso(H) = 1.2Ueq(C). Please check added text.

Structure description top

The title compound is a newly synthesized member of the diacetylenic 1,2-diones, a class of compounds first introduced in 1996 (Faust & Weber, 1996; Faust et al., 1997). The two typifying interconnected ynone moieties of this molecular structure give rise to a rich chemistry that we have explored to form, inter alia, metal-chelating diazabutadienes (Faust, Göbelt & Weber, 1999; Faust, Göbelt et al., 1999), alkyne-substituted N-heterocyclic carbenes (Faust & Göbelt, 2000) and acetylenic phthalocyanines (Faust, 2001). Despite these successful developments, two questions remain about the electronic aspects of these compounds. Firstly, the kinetic stability of dialkynyl diones appears to rely largely on the size of the terminal alkyne substituents. Whereas bulky triisoproylsilyl groups lend excellent stability to the hexadiynedione core, smaller terminal substituents, such as alkyls or the trimethylsilyl group, are insufficient to protect the reactive ynone system from nucleophilic attack (Faust et al., 1997). Similarly, aryl termini shield the reactive core of the molecule most effectively when, as in the case discussed here, they possess sizeable 2,6-substituents flanking the alkyne subunit. The second question concerns the effective conjugation path of the hexa-1,5-diyne-3,4-dione framework. We have speculated that, similar to the related 2,3-dialkynyldiazabutadienes (Faust et al., 1999 Which?), a valid description of dialkynyl diones is that of two interconnected but largely electronically independent bis(ynone) units, rather than that of a species fully delocalized along the hexadiynedione core. The present solid-state study is the first on this class of compounds and was undertaken to shed some light on these matters.

The title compound, (I), with the atomic numbering, is shown in Fig. 1. The molecule crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Inspection of Fig. 1 reveals an extended conformation of the molecule with a formal s-trans geometry [torsion angle O2—C4—C3—O1 175.2 (2) °] around the 1,2-dione subunit. The maximum deviation of the atoms from a plane through C2/C3/C4/C5/O1/O2 is only 0.062 (1) Å For which atom?. The phenyl ring system around C7 is almost perfectly coplanar with the dione unit, as the plane through C1/C2/C3/C7/C8/C12/O1 forms an angle of only 4.2 (1)° with that of the dione substructure. On the other hand, the phenyl ring system around C19 (i.e. a plane through C4/C5/C6/C19/C20/C24) is twisted by about 20.3 (1)° from the plane of the dione moiety.

In terms of π electronic delocalization, it appears that, in the crystal, the electronic interaction between one phenyl group and the ynone portion of the molecule is maximized, whereas that of the other is slightly diminished. The distance between the two carbonyl atoms C3—C4 is 1.535 (2) Å (Table 1), suggesting a rather long Csp2—Csp2 single bond through which little electron density is transmitted. While most other structural parameters within this part of the molecule are within the normal range (Allen et al., 1987), the C—C—C angles around the carbonyl C atoms [i.e. C2—C3—C4 116.7 (1)° and C3—C4—C5 114.5 (1)°] are significantly compressed.

The methyl groups on the 2,6-positions on the aryl rings protrude into the space segment above and below the C1C2 (and C5C6) triple bonds, a structural feature that helps to explain the increased stability of this system towards nucleophilic attack, particularly in solution, where there is free rotation around the C7—C1 (and C6—C19) single bonds. There are no close intramolecular contacts between the methyl H atoms and the carbonyl O atoms.

An inspection of the packing arrangement (Fig. 2) of compound (I) in the crystal reveals that the tert-butyl groups of one molecule reside in the space above the dione subunits of adjacent molecules. In conjunction with the findings above, this might indicate that the planarity of the dione substructure is dictated by the space requirements of the bulky alkyl group, rather than by intramolecular electronic interactions such as π delocalization. The crystal packing forces are enhanced by very weak intermolecular hydrogen bonds between methyl H atoms and the carbonyl O atoms. The relevant distances are depicted as dashed lines in Fig. 2, with details given in Table 2. In this way, chains of centrosymmetric rings develop along [101]. The alkyl substitution of the aryl rings prevents intermolecular ππ stacking interactions.

Computing details top

Data collection: X-AREA (Stoe, 2004); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: Please provide missing details.

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The packing of (I), revealing the closest distances between the O atoms and the methyl groups of neighbouring molecules (broken lines); see Table 2 for details.
bis(4-tert-butyl-2,6-dimethylphenyl)hexa-1,5-diyne-3,4-dione top
Crystal data top
C30H34O2Z = 2
Mr = 426.57F(000) = 460
Triclinic, P1Dx = 1.145 Mg m3
Hall symbol: -P 1Melting point: 437 K
a = 9.3933 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4531 (14) ÅCell parameters from 11904 reflections
c = 11.9823 (13) Åθ = 1.8–25.6°
α = 93.289 (9)°µ = 0.07 mm1
β = 105.303 (9)°T = 213 K
γ = 93.674 (10)°Block, yellow
V = 1237.1 (3) Å30.58 × 0.32 × 0.31 mm
Data collection top
Stoe IPDS 2
diffractometer
4296 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3130 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.055
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 1.8°
rotation scansh = 1111
Absorption correction: integration
X-RED (Stoe, 2004)
k = 1313
Tmin = 0.974, Tmax = 0.991l = 1314
15963 measured reflections
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0663P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4296 reflectionsΔρmax = 0.18 e Å3
300 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (4)
Crystal data top
C30H34O2γ = 93.674 (10)°
Mr = 426.57V = 1237.1 (3) Å3
Triclinic, P1Z = 2
a = 9.3933 (11) ÅMo Kα radiation
b = 11.4531 (14) ŵ = 0.07 mm1
c = 11.9823 (13) ÅT = 213 K
α = 93.289 (9)°0.58 × 0.32 × 0.31 mm
β = 105.303 (9)°
Data collection top
Stoe IPDS 2
diffractometer
4296 independent reflections
Absorption correction: integration
X-RED (Stoe, 2004)
3130 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.991Rint = 0.055
15963 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.00Δρmax = 0.18 e Å3
4296 reflectionsΔρmin = 0.20 e Å3
300 parameters
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
C11.01527 (16)0.29304 (13)0.97660 (14)0.0385 (4)
C20.92104 (17)0.35511 (13)0.93211 (15)0.0417 (4)
C30.79814 (16)0.42133 (13)0.88130 (14)0.0395 (4)
C40.82169 (16)0.50726 (13)0.79288 (14)0.0381 (4)
C50.69143 (16)0.56197 (13)0.73571 (15)0.0408 (4)
C60.57402 (16)0.59718 (12)0.68861 (14)0.0380 (4)
C71.12465 (15)0.21929 (12)1.03434 (13)0.0341 (3)
C81.26782 (16)0.22913 (12)1.01846 (13)0.0342 (3)
C91.37194 (15)0.15815 (12)1.07939 (13)0.0337 (3)
H91.46820.16441.06970.040*
C101.33885 (15)0.07865 (12)1.15380 (13)0.0324 (3)
C111.19492 (15)0.07044 (13)1.16644 (13)0.0363 (3)
H111.17070.01661.21620.044*
C121.08671 (15)0.13850 (13)1.10840 (13)0.0363 (3)
C131.30931 (17)0.31482 (14)0.93975 (15)0.0440 (4)
H13A1.32610.39320.97850.053*
H13B1.22960.31320.86900.053*
H13C1.39900.29340.92090.053*
C141.45266 (15)0.00149 (12)1.21979 (13)0.0349 (3)
C151.60622 (16)0.02569 (14)1.20256 (16)0.0463 (4)
H15A1.64010.10691.22890.056*
H15B1.60160.01281.12090.056*
H15C1.67470.02531.24690.056*
C161.39901 (17)0.12889 (13)1.17445 (15)0.0415 (4)
H16A1.38880.13801.09170.050*
H16B1.30390.14861.18910.050*
H16C1.47040.18071.21390.050*
C171.46431 (18)0.01323 (14)1.34964 (14)0.0452 (4)
H17A1.36800.00621.36220.054*
H17B1.49790.09391.37860.054*
H17C1.53450.03871.39050.054*
C180.93255 (17)0.12525 (16)1.12358 (16)0.0476 (4)
H18A0.86390.09321.05120.057*
H18B0.90410.20141.14550.057*
H18C0.93030.07271.18390.057*
C190.43427 (15)0.63724 (11)0.63012 (14)0.0347 (3)
C200.31617 (15)0.63061 (12)0.68204 (13)0.0349 (3)
C210.18203 (15)0.66959 (12)0.62232 (13)0.0341 (3)
H210.10230.66490.65600.041*
C220.16117 (14)0.71543 (11)0.51427 (13)0.0315 (3)
C230.27989 (15)0.71885 (12)0.46446 (14)0.0341 (3)
H230.26720.74790.39100.041*
C240.41663 (15)0.68043 (12)0.52039 (14)0.0355 (3)
C250.33359 (17)0.58291 (14)0.79879 (15)0.0460 (4)
H25A0.38790.64170.85910.055*
H25B0.38750.51310.80260.055*
H25C0.23660.56310.81000.055*
C260.00963 (15)0.75651 (12)0.45258 (13)0.0343 (3)
C270.09986 (16)0.64772 (14)0.41172 (15)0.0440 (4)
H27C0.19570.67160.37060.053*
H27B0.10940.60680.47840.053*
H27A0.06370.59590.36030.053*
C280.04462 (17)0.83650 (14)0.53718 (15)0.0431 (4)
H28A0.03000.90070.56970.052*
H28B0.06230.79170.59920.052*
H28C0.13590.86770.49610.052*
C290.01637 (17)0.82469 (15)0.34774 (15)0.0452 (4)
H29A0.04420.77380.29080.054*
H29B0.08920.89150.37250.054*
H29C0.08000.85200.31350.054*
C300.54216 (16)0.68559 (14)0.46463 (16)0.0437 (4)
H30A0.58310.60990.46590.052*
H30B0.61850.74500.50700.052*
H30C0.50610.70520.38490.052*
O10.68026 (12)0.41040 (10)0.90492 (11)0.0527 (3)
O20.94217 (11)0.52403 (10)0.77459 (11)0.0493 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0407 (8)0.0387 (8)0.0337 (9)0.0092 (6)0.0046 (6)0.0010 (6)
C20.0416 (8)0.0408 (8)0.0409 (10)0.0111 (7)0.0059 (7)0.0034 (7)
C30.0363 (8)0.0385 (8)0.0417 (10)0.0094 (6)0.0059 (7)0.0017 (7)
C40.0350 (8)0.0395 (8)0.0377 (9)0.0099 (6)0.0054 (6)0.0001 (7)
C50.0374 (8)0.0398 (8)0.0439 (10)0.0088 (6)0.0067 (7)0.0061 (7)
C60.0368 (8)0.0317 (7)0.0434 (10)0.0045 (6)0.0061 (7)0.0051 (6)
C70.0369 (8)0.0344 (7)0.0291 (8)0.0100 (6)0.0038 (6)0.0016 (6)
C80.0392 (8)0.0319 (7)0.0307 (9)0.0060 (6)0.0071 (6)0.0032 (6)
C90.0326 (7)0.0341 (7)0.0346 (9)0.0059 (6)0.0087 (6)0.0042 (6)
C100.0352 (7)0.0317 (7)0.0294 (8)0.0055 (6)0.0062 (6)0.0027 (6)
C110.0379 (8)0.0403 (8)0.0324 (9)0.0067 (6)0.0100 (6)0.0099 (6)
C120.0358 (7)0.0411 (8)0.0316 (9)0.0080 (6)0.0078 (6)0.0013 (6)
C130.0461 (9)0.0431 (8)0.0442 (10)0.0095 (7)0.0111 (7)0.0146 (7)
C140.0361 (7)0.0342 (7)0.0330 (9)0.0077 (6)0.0047 (6)0.0073 (6)
C150.0366 (8)0.0469 (9)0.0538 (11)0.0123 (7)0.0053 (7)0.0125 (8)
C160.0456 (9)0.0367 (8)0.0406 (10)0.0105 (6)0.0062 (7)0.0061 (7)
C170.0517 (9)0.0440 (9)0.0357 (10)0.0126 (7)0.0021 (7)0.0064 (7)
C180.0379 (8)0.0639 (10)0.0440 (11)0.0125 (7)0.0132 (7)0.0095 (8)
C190.0316 (7)0.0275 (7)0.0423 (10)0.0049 (5)0.0038 (6)0.0063 (6)
C200.0355 (7)0.0283 (7)0.0379 (9)0.0011 (5)0.0042 (6)0.0063 (6)
C210.0322 (7)0.0316 (7)0.0388 (9)0.0024 (6)0.0097 (6)0.0052 (6)
C220.0302 (7)0.0267 (7)0.0355 (9)0.0038 (5)0.0049 (6)0.0031 (6)
C230.0331 (7)0.0324 (7)0.0374 (9)0.0061 (5)0.0083 (6)0.0082 (6)
C240.0321 (7)0.0288 (7)0.0451 (10)0.0050 (5)0.0082 (6)0.0058 (6)
C250.0428 (8)0.0478 (9)0.0441 (10)0.0022 (7)0.0039 (7)0.0163 (7)
C260.0299 (7)0.0362 (7)0.0362 (9)0.0089 (6)0.0061 (6)0.0045 (6)
C270.0313 (7)0.0472 (9)0.0507 (11)0.0058 (6)0.0066 (7)0.0017 (7)
C280.0414 (8)0.0432 (8)0.0454 (10)0.0149 (6)0.0104 (7)0.0035 (7)
C290.0386 (8)0.0543 (9)0.0434 (10)0.0170 (7)0.0072 (7)0.0134 (8)
C300.0350 (8)0.0454 (9)0.0539 (11)0.0107 (6)0.0141 (7)0.0116 (7)
O10.0446 (7)0.0519 (7)0.0672 (9)0.0154 (5)0.0197 (6)0.0176 (6)
O20.0372 (6)0.0623 (7)0.0520 (8)0.0146 (5)0.0139 (5)0.0126 (6)
Geometric parameters (Å, º) top
C1—C21.203 (2)C17—H17C0.97
C1—C71.4321 (19)C18—H18A0.97
C2—C31.440 (2)C18—H18B0.97
C3—O11.2139 (18)C18—H18C0.97
C3—C41.535 (2)C19—C241.404 (2)
C4—O21.2139 (18)C19—C201.408 (2)
C4—C51.437 (2)C20—C211.390 (2)
C5—C61.205 (2)C20—C251.504 (2)
C6—C191.4330 (19)C21—C221.395 (2)
C7—C81.406 (2)C21—H210.94
C7—C121.410 (2)C22—C231.396 (2)
C8—C91.3941 (19)C22—C261.5376 (18)
C8—C131.502 (2)C23—C241.3945 (19)
C9—C101.387 (2)C23—H230.94
C9—H90.94C24—C301.501 (2)
C10—C111.397 (2)C25—H25A0.97
C10—C141.5406 (18)C25—H25B0.97
C11—C121.384 (2)C25—H25C0.97
C11—H110.94C26—C291.530 (2)
C12—C181.506 (2)C26—C271.533 (2)
C13—H13A0.97C26—C281.534 (2)
C13—H13B0.97C27—H27C0.97
C13—H13C0.97C27—H27B0.97
C14—C151.526 (2)C27—H27A0.97
C14—C171.529 (2)C28—H28A0.97
C14—C161.532 (2)C28—H28B0.97
C15—H15A0.97C28—H28C0.97
C15—H15B0.97C29—H29A0.97
C15—H15C0.97C29—H29B0.97
C16—H16A0.97C29—H29C0.97
C16—H16B0.97C30—H30A0.97
C16—H16C0.97C30—H30B0.97
C17—H17A0.97C30—H30C0.97
C17—H17B0.97
C2—C1—C7177.24 (17)C12—C18—H18B109.5
C1—C2—C3174.50 (17)H18A—C18—H18B109.5
O1—C3—C2122.82 (15)C12—C18—H18C109.5
O1—C3—C4120.52 (13)H18A—C18—H18C109.5
C2—C3—C4116.65 (13)H18B—C18—H18C109.5
O2—C4—C5124.80 (15)C24—C19—C20121.01 (12)
O2—C4—C3120.69 (13)C24—C19—C6119.18 (13)
C5—C4—C3114.51 (13)C20—C19—C6119.80 (14)
C6—C5—C4173.22 (16)C21—C20—C19118.13 (14)
C5—C6—C19178.60 (18)C21—C20—C25120.55 (14)
C8—C7—C12120.92 (12)C19—C20—C25121.32 (13)
C8—C7—C1120.21 (13)C20—C21—C22122.53 (13)
C12—C7—C1118.86 (13)C20—C21—H21118.7
C9—C8—C7118.14 (13)C22—C21—H21118.7
C9—C8—C13120.52 (13)C21—C22—C23117.80 (12)
C7—C8—C13121.34 (12)C21—C22—C26119.89 (12)
C10—C9—C8122.45 (13)C23—C22—C26122.29 (13)
C10—C9—H9118.8C24—C23—C22122.01 (14)
C8—C9—H9118.8C24—C23—H23119.0
C9—C10—C11117.78 (12)C22—C23—H23119.0
C9—C10—C14122.69 (12)C23—C24—C19118.50 (13)
C11—C10—C14119.52 (12)C23—C24—C30120.69 (14)
C12—C11—C10122.49 (13)C19—C24—C30120.81 (13)
C12—C11—H11118.8C20—C25—H25A109.5
C10—C11—H11118.8C20—C25—H25B109.5
C11—C12—C7118.21 (13)H25A—C25—H25B109.5
C11—C12—C18120.53 (14)C20—C25—H25C109.5
C7—C12—C18121.27 (13)H25A—C25—H25C109.5
C8—C13—H13A109.5H25B—C25—H25C109.5
C8—C13—H13B109.5C29—C26—C27109.10 (13)
H13A—C13—H13B109.5C29—C26—C28108.23 (12)
C8—C13—H13C109.5C27—C26—C28109.55 (12)
H13A—C13—H13C109.5C29—C26—C22112.03 (12)
H13B—C13—H13C109.5C27—C26—C22108.11 (11)
C15—C14—C17108.51 (13)C28—C26—C22109.80 (12)
C15—C14—C16108.77 (13)C26—C27—H27C109.5
C17—C14—C16109.25 (13)C26—C27—H27B109.5
C15—C14—C10112.22 (12)H27C—C27—H27B109.5
C17—C14—C10109.84 (12)C26—C27—H27A109.5
C16—C14—C10108.20 (12)H27C—C27—H27A109.5
C14—C15—H15A109.5H27B—C27—H27A109.5
C14—C15—H15B109.5C26—C28—H28A109.5
H15A—C15—H15B109.5C26—C28—H28B109.5
C14—C15—H15C109.5H28A—C28—H28B109.5
H15A—C15—H15C109.5C26—C28—H28C109.5
H15B—C15—H15C109.5H28A—C28—H28C109.5
C14—C16—H16A109.5H28B—C28—H28C109.5
C14—C16—H16B109.5C26—C29—H29A109.5
H16A—C16—H16B109.5C26—C29—H29B109.5
C14—C16—H16C109.5H29A—C29—H29B109.5
H16A—C16—H16C109.5C26—C29—H29C109.5
H16B—C16—H16C109.5H29A—C29—H29C109.5
C14—C17—H17A109.5H29B—C29—H29C109.5
C14—C17—H17B109.5C24—C30—H30A109.5
H17A—C17—H17B109.5C24—C30—H30B109.5
C14—C17—H17C109.5H30A—C30—H30B109.5
H17A—C17—H17C109.5C24—C30—H30C109.5
H17B—C17—H17C109.5H30A—C30—H30C109.5
C12—C18—H18A109.5H30B—C30—H30C109.5
O1—C3—C4—O2175.22 (15)C9—C10—C14—C16114.48 (15)
C2—C3—C4—O25.5 (2)C11—C10—C14—C1664.13 (18)
O1—C3—C4—C55.5 (2)C24—C19—C20—C210.9 (2)
C2—C3—C4—C5173.76 (14)C6—C19—C20—C21179.58 (13)
C12—C7—C8—C91.0 (2)C24—C19—C20—C25179.14 (14)
C1—C7—C8—C9177.96 (14)C6—C19—C20—C250.5 (2)
C12—C7—C8—C13179.96 (15)C19—C20—C21—C220.5 (2)
C1—C7—C8—C131.1 (2)C25—C20—C21—C22179.44 (14)
C7—C8—C9—C100.3 (2)C20—C21—C22—C231.6 (2)
C13—C8—C9—C10179.38 (14)C20—C21—C22—C26179.73 (13)
C8—C9—C10—C110.3 (2)C21—C22—C23—C241.3 (2)
C8—C9—C10—C14178.94 (14)C26—C22—C23—C24179.38 (13)
C9—C10—C11—C120.3 (2)C22—C23—C24—C190.1 (2)
C14—C10—C11—C12179.02 (14)C22—C23—C24—C30179.83 (14)
C10—C11—C12—C70.3 (2)C20—C19—C24—C231.2 (2)
C10—C11—C12—C18179.14 (14)C6—C19—C24—C23179.86 (13)
C8—C7—C12—C111.0 (2)C20—C19—C24—C30179.05 (13)
C1—C7—C12—C11177.99 (14)C6—C19—C24—C300.4 (2)
C8—C7—C12—C18178.45 (14)C21—C22—C26—C29169.16 (13)
C1—C7—C12—C182.6 (2)C23—C22—C26—C2912.79 (19)
C9—C10—C14—C155.5 (2)C21—C22—C26—C2770.59 (17)
C11—C10—C14—C15175.86 (14)C23—C22—C26—C27107.46 (15)
C9—C10—C14—C17126.34 (15)C21—C22—C26—C2848.87 (17)
C11—C10—C14—C1755.05 (18)C23—C22—C26—C28133.07 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.972.593.545 (2)168
C27—H27A···O2ii0.972.593.558 (2)173
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC30H34O2
Mr426.57
Crystal system, space groupTriclinic, P1
Temperature (K)213
a, b, c (Å)9.3933 (11), 11.4531 (14), 11.9823 (13)
α, β, γ (°)93.289 (9), 105.303 (9), 93.674 (10)
V3)1237.1 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.58 × 0.32 × 0.31
Data collection
DiffractometerStoe IPDS 2
Absorption correctionIntegration
X-RED (Stoe, 2004)
Tmin, Tmax0.974, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
15963, 4296, 3130
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.107, 1.00
No. of reflections4296
No. of parameters300
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.20

Computer programs: X-AREA (Stoe, 2004), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), Please provide missing details.

Selected geometric parameters (Å, º) top
C1—C21.203 (2)C4—C51.437 (2)
C1—C71.4321 (19)C5—C61.205 (2)
C2—C31.440 (2)C6—C191.4330 (19)
C3—O11.2139 (18)C8—C131.502 (2)
C3—C41.535 (2)C11—C121.384 (2)
C4—O21.2139 (18)
C1—C2—C3174.50 (17)C5—C4—C3114.51 (13)
C2—C3—C4116.65 (13)C6—C5—C4173.22 (16)
O1—C3—C4—O2175.22 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.972.593.545 (2)168
C27—H27A···O2ii0.972.593.558 (2)173
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+1, z+1.
 

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