A diaryl-terminated hexa-1,5-diyne-3,4-dione

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.

S1. Comment

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 C1≡C2 (and C5≡C6) 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 π–π stacking interactions.

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2U_eq(C). Please check added text.

Computing details

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

	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.
	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

Crystal data

C30H34O2	Z = 2
Mr = 426.57	F(000) = 460
Triclinic, P1	Dx = 1.145 Mg m^−3
Hall symbol: -P 1	Melting point: 437 K
a = 9.3933 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4531 (14) Å	Cell parameters from 11904 reflections
c = 11.9823 (13) Å	θ = 1.8–25.6°
α = 93.289 (9)°	µ = 0.07 mm^−1
β = 105.303 (9)°	T = 213 K
γ = 93.674 (10)°	Block, yellow
V = 1237.1 (3) Å^3	0.58 × 0.32 × 0.31 mm

Data collection

Stoe IPDS 2 diffractometer	4296 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3130 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.055
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
rotation scans	h = −11→11
Absorption correction: integration X-RED (Stoe, 2004)	k = −13→13
Tmin = 0.974, Tmax = 0.991	l = −13→14
15963 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0663P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
4296 reflections	Δρmax = 0.18 e Å^−3
300 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.01527 (16)	0.29304 (13)	0.97660 (14)	0.0385 (4)
C2	0.92104 (17)	0.35511 (13)	0.93211 (15)	0.0417 (4)
C3	0.79814 (16)	0.42133 (13)	0.88130 (14)	0.0395 (4)
C4	0.82169 (16)	0.50726 (13)	0.79288 (14)	0.0381 (4)
C5	0.69143 (16)	0.56197 (13)	0.73571 (15)	0.0408 (4)
C6	0.57402 (16)	0.59718 (12)	0.68861 (14)	0.0380 (4)
C7	1.12465 (15)	0.21929 (12)	1.03434 (13)	0.0341 (3)
C8	1.26782 (16)	0.22913 (12)	1.01846 (13)	0.0342 (3)
C9	1.37194 (15)	0.15815 (12)	1.07939 (13)	0.0337 (3)
H9	1.4682	0.1644	1.0697	0.040*
C10	1.33885 (15)	0.07865 (12)	1.15380 (13)	0.0324 (3)
C11	1.19492 (15)	0.07044 (13)	1.16644 (13)	0.0363 (3)
H11	1.1707	0.0166	1.2162	0.044*
C12	1.08671 (15)	0.13850 (13)	1.10840 (13)	0.0363 (3)
C13	1.30931 (17)	0.31482 (14)	0.93975 (15)	0.0440 (4)
H13A	1.3261	0.3932	0.9785	0.053*
H13B	1.2296	0.3132	0.8690	0.053*
H13C	1.3990	0.2934	0.9209	0.053*
C14	1.45266 (15)	−0.00149 (12)	1.21979 (13)	0.0349 (3)
C15	1.60622 (16)	0.02569 (14)	1.20256 (16)	0.0463 (4)
H15A	1.6401	0.1069	1.2289	0.056*
H15B	1.6016	0.0128	1.1209	0.056*
H15C	1.6747	−0.0253	1.2469	0.056*
C16	1.39901 (17)	−0.12889 (13)	1.17445 (15)	0.0415 (4)
H16A	1.3888	−0.1380	1.0917	0.050*
H16B	1.3039	−0.1486	1.1891	0.050*
H16C	1.4704	−0.1807	1.2139	0.050*
C17	1.46431 (18)	0.01323 (14)	1.34964 (14)	0.0452 (4)
H17A	1.3680	−0.0062	1.3622	0.054*
H17B	1.4979	0.0939	1.3786	0.054*
H17C	1.5345	−0.0387	1.3905	0.054*
C18	0.93255 (17)	0.12525 (16)	1.12358 (16)	0.0476 (4)
H18A	0.8639	0.0932	1.0512	0.057*
H18B	0.9041	0.2014	1.1455	0.057*
H18C	0.9303	0.0727	1.1839	0.057*
C19	0.43427 (15)	0.63724 (11)	0.63012 (14)	0.0347 (3)
C20	0.31617 (15)	0.63061 (12)	0.68204 (13)	0.0349 (3)
C21	0.18203 (15)	0.66959 (12)	0.62232 (13)	0.0341 (3)
H21	0.1023	0.6649	0.6560	0.041*
C22	0.16117 (14)	0.71543 (11)	0.51427 (13)	0.0315 (3)
C23	0.27989 (15)	0.71885 (12)	0.46446 (14)	0.0341 (3)
H23	0.2672	0.7479	0.3910	0.041*
C24	0.41663 (15)	0.68043 (12)	0.52039 (14)	0.0355 (3)
C25	0.33359 (17)	0.58291 (14)	0.79879 (15)	0.0460 (4)
H25A	0.3879	0.6417	0.8591	0.055*
H25B	0.3875	0.5131	0.8026	0.055*
H25C	0.2366	0.5631	0.8100	0.055*
C26	0.00963 (15)	0.75651 (12)	0.45258 (13)	0.0343 (3)
C27	−0.09986 (16)	0.64772 (14)	0.41172 (15)	0.0440 (4)
H27C	−0.1957	0.6716	0.3706	0.053*
H27B	−0.1094	0.6068	0.4784	0.053*
H27A	−0.0637	0.5959	0.3603	0.053*
C28	−0.04462 (17)	0.83650 (14)	0.53718 (15)	0.0431 (4)
H28A	0.0300	0.9007	0.5697	0.052*
H28B	−0.0623	0.7917	0.5992	0.052*
H28C	−0.1359	0.8677	0.4961	0.052*
C29	0.01637 (17)	0.82469 (15)	0.34774 (15)	0.0452 (4)
H29A	0.0442	0.7738	0.2908	0.054*
H29B	0.0892	0.8915	0.3725	0.054*
H29C	−0.0800	0.8520	0.3135	0.054*
C30	0.54216 (16)	0.68559 (14)	0.46463 (16)	0.0437 (4)
H30A	0.5831	0.6099	0.4659	0.052*
H30B	0.6185	0.7450	0.5070	0.052*
H30C	0.5061	0.7052	0.3849	0.052*
O1	0.68026 (12)	0.41040 (10)	0.90492 (11)	0.0527 (3)
O2	0.94217 (11)	0.52403 (10)	0.77459 (11)	0.0493 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0407 (8)	0.0387 (8)	0.0337 (9)	0.0092 (6)	0.0046 (6)	0.0010 (6)
C2	0.0416 (8)	0.0408 (8)	0.0409 (10)	0.0111 (7)	0.0059 (7)	0.0034 (7)
C3	0.0363 (8)	0.0385 (8)	0.0417 (10)	0.0094 (6)	0.0059 (7)	0.0017 (7)
C4	0.0350 (8)	0.0395 (8)	0.0377 (9)	0.0099 (6)	0.0054 (6)	−0.0001 (7)
C5	0.0374 (8)	0.0398 (8)	0.0439 (10)	0.0088 (6)	0.0067 (7)	0.0061 (7)
C6	0.0368 (8)	0.0317 (7)	0.0434 (10)	0.0045 (6)	0.0061 (7)	0.0051 (6)
C7	0.0369 (8)	0.0344 (7)	0.0291 (8)	0.0100 (6)	0.0038 (6)	0.0016 (6)
C8	0.0392 (8)	0.0319 (7)	0.0307 (9)	0.0060 (6)	0.0071 (6)	0.0032 (6)
C9	0.0326 (7)	0.0341 (7)	0.0346 (9)	0.0059 (6)	0.0087 (6)	0.0042 (6)
C10	0.0352 (7)	0.0317 (7)	0.0294 (8)	0.0055 (6)	0.0062 (6)	0.0027 (6)
C11	0.0379 (8)	0.0403 (8)	0.0324 (9)	0.0067 (6)	0.0100 (6)	0.0099 (6)
C12	0.0358 (7)	0.0411 (8)	0.0316 (9)	0.0080 (6)	0.0078 (6)	0.0013 (6)
C13	0.0461 (9)	0.0431 (8)	0.0442 (10)	0.0095 (7)	0.0111 (7)	0.0146 (7)
C14	0.0361 (7)	0.0342 (7)	0.0330 (9)	0.0077 (6)	0.0047 (6)	0.0073 (6)
C15	0.0366 (8)	0.0469 (9)	0.0538 (11)	0.0123 (7)	0.0053 (7)	0.0125 (8)
C16	0.0456 (9)	0.0367 (8)	0.0406 (10)	0.0105 (6)	0.0062 (7)	0.0061 (7)
C17	0.0517 (9)	0.0440 (9)	0.0357 (10)	0.0126 (7)	0.0021 (7)	0.0064 (7)
C18	0.0379 (8)	0.0639 (10)	0.0440 (11)	0.0125 (7)	0.0132 (7)	0.0095 (8)
C19	0.0316 (7)	0.0275 (7)	0.0423 (10)	0.0049 (5)	0.0038 (6)	0.0063 (6)
C20	0.0355 (7)	0.0283 (7)	0.0379 (9)	0.0011 (5)	0.0042 (6)	0.0063 (6)
C21	0.0322 (7)	0.0316 (7)	0.0388 (9)	0.0024 (6)	0.0097 (6)	0.0052 (6)
C22	0.0302 (7)	0.0267 (7)	0.0355 (9)	0.0038 (5)	0.0049 (6)	0.0031 (6)
C23	0.0331 (7)	0.0324 (7)	0.0374 (9)	0.0061 (5)	0.0083 (6)	0.0082 (6)
C24	0.0321 (7)	0.0288 (7)	0.0451 (10)	0.0050 (5)	0.0082 (6)	0.0058 (6)
C25	0.0428 (8)	0.0478 (9)	0.0441 (10)	0.0022 (7)	0.0039 (7)	0.0163 (7)
C26	0.0299 (7)	0.0362 (7)	0.0362 (9)	0.0089 (6)	0.0061 (6)	0.0045 (6)
C27	0.0313 (7)	0.0472 (9)	0.0507 (11)	0.0058 (6)	0.0066 (7)	−0.0017 (7)
C28	0.0414 (8)	0.0432 (8)	0.0454 (10)	0.0149 (6)	0.0104 (7)	0.0035 (7)
C29	0.0386 (8)	0.0543 (9)	0.0434 (10)	0.0170 (7)	0.0072 (7)	0.0134 (8)
C30	0.0350 (8)	0.0454 (9)	0.0539 (11)	0.0107 (6)	0.0141 (7)	0.0116 (7)
O1	0.0446 (7)	0.0519 (7)	0.0672 (9)	0.0154 (5)	0.0197 (6)	0.0176 (6)
O2	0.0372 (6)	0.0623 (7)	0.0520 (8)	0.0146 (5)	0.0139 (5)	0.0126 (6)

Geometric parameters (Å, º)

C1—C2	1.203 (2)	C17—H17C	0.97
C1—C7	1.4321 (19)	C18—H18A	0.97
C2—C3	1.440 (2)	C18—H18B	0.97
C3—O1	1.2139 (18)	C18—H18C	0.97
C3—C4	1.535 (2)	C19—C24	1.404 (2)
C4—O2	1.2139 (18)	C19—C20	1.408 (2)
C4—C5	1.437 (2)	C20—C21	1.390 (2)
C5—C6	1.205 (2)	C20—C25	1.504 (2)
C6—C19	1.4330 (19)	C21—C22	1.395 (2)
C7—C8	1.406 (2)	C21—H21	0.94
C7—C12	1.410 (2)	C22—C23	1.396 (2)
C8—C9	1.3941 (19)	C22—C26	1.5376 (18)
C8—C13	1.502 (2)	C23—C24	1.3945 (19)
C9—C10	1.387 (2)	C23—H23	0.94
C9—H9	0.94	C24—C30	1.501 (2)
C10—C11	1.397 (2)	C25—H25A	0.97
C10—C14	1.5406 (18)	C25—H25B	0.97
C11—C12	1.384 (2)	C25—H25C	0.97
C11—H11	0.94	C26—C29	1.530 (2)
C12—C18	1.506 (2)	C26—C27	1.533 (2)
C13—H13A	0.97	C26—C28	1.534 (2)
C13—H13B	0.97	C27—H27C	0.97
C13—H13C	0.97	C27—H27B	0.97
C14—C15	1.526 (2)	C27—H27A	0.97
C14—C17	1.529 (2)	C28—H28A	0.97
C14—C16	1.532 (2)	C28—H28B	0.97
C15—H15A	0.97	C28—H28C	0.97
C15—H15B	0.97	C29—H29A	0.97
C15—H15C	0.97	C29—H29B	0.97
C16—H16A	0.97	C29—H29C	0.97
C16—H16B	0.97	C30—H30A	0.97
C16—H16C	0.97	C30—H30B	0.97
C17—H17A	0.97	C30—H30C	0.97
C17—H17B	0.97
C2—C1—C7	177.24 (17)	C12—C18—H18B	109.5
C1—C2—C3	174.50 (17)	H18A—C18—H18B	109.5
O1—C3—C2	122.82 (15)	C12—C18—H18C	109.5
O1—C3—C4	120.52 (13)	H18A—C18—H18C	109.5
C2—C3—C4	116.65 (13)	H18B—C18—H18C	109.5
O2—C4—C5	124.80 (15)	C24—C19—C20	121.01 (12)
O2—C4—C3	120.69 (13)	C24—C19—C6	119.18 (13)
C5—C4—C3	114.51 (13)	C20—C19—C6	119.80 (14)
C6—C5—C4	173.22 (16)	C21—C20—C19	118.13 (14)
C5—C6—C19	178.60 (18)	C21—C20—C25	120.55 (14)
C8—C7—C12	120.92 (12)	C19—C20—C25	121.32 (13)
C8—C7—C1	120.21 (13)	C20—C21—C22	122.53 (13)
C12—C7—C1	118.86 (13)	C20—C21—H21	118.7
C9—C8—C7	118.14 (13)	C22—C21—H21	118.7
C9—C8—C13	120.52 (13)	C21—C22—C23	117.80 (12)
C7—C8—C13	121.34 (12)	C21—C22—C26	119.89 (12)
C10—C9—C8	122.45 (13)	C23—C22—C26	122.29 (13)
C10—C9—H9	118.8	C24—C23—C22	122.01 (14)
C8—C9—H9	118.8	C24—C23—H23	119.0
C9—C10—C11	117.78 (12)	C22—C23—H23	119.0
C9—C10—C14	122.69 (12)	C23—C24—C19	118.50 (13)
C11—C10—C14	119.52 (12)	C23—C24—C30	120.69 (14)
C12—C11—C10	122.49 (13)	C19—C24—C30	120.81 (13)
C12—C11—H11	118.8	C20—C25—H25A	109.5
C10—C11—H11	118.8	C20—C25—H25B	109.5
C11—C12—C7	118.21 (13)	H25A—C25—H25B	109.5
C11—C12—C18	120.53 (14)	C20—C25—H25C	109.5
C7—C12—C18	121.27 (13)	H25A—C25—H25C	109.5
C8—C13—H13A	109.5	H25B—C25—H25C	109.5
C8—C13—H13B	109.5	C29—C26—C27	109.10 (13)
H13A—C13—H13B	109.5	C29—C26—C28	108.23 (12)
C8—C13—H13C	109.5	C27—C26—C28	109.55 (12)
H13A—C13—H13C	109.5	C29—C26—C22	112.03 (12)
H13B—C13—H13C	109.5	C27—C26—C22	108.11 (11)
C15—C14—C17	108.51 (13)	C28—C26—C22	109.80 (12)
C15—C14—C16	108.77 (13)	C26—C27—H27C	109.5
C17—C14—C16	109.25 (13)	C26—C27—H27B	109.5
C15—C14—C10	112.22 (12)	H27C—C27—H27B	109.5
C17—C14—C10	109.84 (12)	C26—C27—H27A	109.5
C16—C14—C10	108.20 (12)	H27C—C27—H27A	109.5
C14—C15—H15A	109.5	H27B—C27—H27A	109.5
C14—C15—H15B	109.5	C26—C28—H28A	109.5
H15A—C15—H15B	109.5	C26—C28—H28B	109.5
C14—C15—H15C	109.5	H28A—C28—H28B	109.5
H15A—C15—H15C	109.5	C26—C28—H28C	109.5
H15B—C15—H15C	109.5	H28A—C28—H28C	109.5
C14—C16—H16A	109.5	H28B—C28—H28C	109.5
C14—C16—H16B	109.5	C26—C29—H29A	109.5
H16A—C16—H16B	109.5	C26—C29—H29B	109.5
C14—C16—H16C	109.5	H29A—C29—H29B	109.5
H16A—C16—H16C	109.5	C26—C29—H29C	109.5
H16B—C16—H16C	109.5	H29A—C29—H29C	109.5
C14—C17—H17A	109.5	H29B—C29—H29C	109.5
C14—C17—H17B	109.5	C24—C30—H30A	109.5
H17A—C17—H17B	109.5	C24—C30—H30B	109.5
C14—C17—H17C	109.5	H30A—C30—H30B	109.5
H17A—C17—H17C	109.5	C24—C30—H30C	109.5
H17B—C17—H17C	109.5	H30A—C30—H30C	109.5
C12—C18—H18A	109.5	H30B—C30—H30C	109.5
O1—C3—C4—O2	175.22 (15)	C9—C10—C14—C16	−114.48 (15)
C2—C3—C4—O2	−5.5 (2)	C11—C10—C14—C16	64.13 (18)
O1—C3—C4—C5	−5.5 (2)	C24—C19—C20—C21	−0.9 (2)
C2—C3—C4—C5	173.76 (14)	C6—C19—C20—C21	−179.58 (13)
C12—C7—C8—C9	−1.0 (2)	C24—C19—C20—C25	179.14 (14)
C1—C7—C8—C9	177.96 (14)	C6—C19—C20—C25	0.5 (2)
C12—C7—C8—C13	179.96 (15)	C19—C20—C21—C22	−0.5 (2)
C1—C7—C8—C13	−1.1 (2)	C25—C20—C21—C22	179.44 (14)
C7—C8—C9—C10	0.3 (2)	C20—C21—C22—C23	1.6 (2)
C13—C8—C9—C10	179.38 (14)	C20—C21—C22—C26	179.73 (13)
C8—C9—C10—C11	0.3 (2)	C21—C22—C23—C24	−1.3 (2)
C8—C9—C10—C14	178.94 (14)	C26—C22—C23—C24	−179.38 (13)
C9—C10—C11—C12	−0.3 (2)	C22—C23—C24—C19	−0.1 (2)
C14—C10—C11—C12	−179.02 (14)	C22—C23—C24—C30	−179.83 (14)
C10—C11—C12—C7	−0.3 (2)	C20—C19—C24—C23	1.2 (2)
C10—C11—C12—C18	179.14 (14)	C6—C19—C24—C23	179.86 (13)
C8—C7—C12—C11	1.0 (2)	C20—C19—C24—C30	−179.05 (13)
C1—C7—C12—C11	−177.99 (14)	C6—C19—C24—C30	−0.4 (2)
C8—C7—C12—C18	−178.45 (14)	C21—C22—C26—C29	169.16 (13)
C1—C7—C12—C18	2.6 (2)	C23—C22—C26—C29	−12.79 (19)
C9—C10—C14—C15	5.5 (2)	C21—C22—C26—C27	−70.59 (17)
C11—C10—C14—C15	−175.86 (14)	C23—C22—C26—C27	107.46 (15)
C9—C10—C14—C17	126.34 (15)	C21—C22—C26—C28	48.87 (17)
C11—C10—C14—C17	−55.05 (18)	C23—C22—C26—C28	−133.07 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1^i	0.97	2.59	3.545 (2)	168
C27—H27A···O2^ii	0.97	2.59	3.558 (2)	173

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.