Dichloro(4,4'-dinonyl-2,2'-bipyridine-[kappa]²N,N')platinum(II)

The title compound, [PtCl₂(C₂₈H₄₄N₂)], is a new square-planar Pt^II complex con­taining a bi­pyridine moiety with two long alkyl-chain substituents. The complex forms a segregated packing structure made up of the alkyl-chain layers and paired coordination sites.

S1. Comment

The introduction of long alkyl chains to various chemical systems is an important strategy for the construction of self-assembled nanostructures. Some approaches to the construction and control of supramolecular systems based on Pt complexes have been reported recently (Neve et al., 1997; Wang et al., 2000; Kimizuka et al., 2000). We report here the crystal structure of the title novel Pt complex containing bipyridine with two long alkyl-chains, [PtCl₂(dnbpy)] (dnbpy is 4,4'-dinonyl-2,2'-bipyridine), (I). \sch

The molecular structure of the complex is shown in Fig. 1. The two alkyl chains are extended out of the coordination plane and are ordered almost parallel to the bc plane to make an alkyl-chain layer, as shown in Fig. 2. Between the alkyl-chain layers, square-planar coordination sites are paired, forming a face-to-face arrangement related to the inversion centre. As shown in Fig. 3, the coordination planes contact mainly via the π–π interactions of the bipyridine ligands, with an interplanar distance of 3.39 (3) Å. The Pt atoms are thus apart from each other, indicating no interaction [Pt···Pt 5.3688 (5) Å].

The stacking features of (I) are different from those for both forms of the parent complex, [PtCl₂(bpy)] (bpy is 2,2'-bipyridine), namely the red form containing the Pt···Pt linear chain (Connick et al., 1996; Osborn & Rodger, 1974) and the yellow form containing an infinite π–π stack (Herber et al., 1994). The arrangement for (I) is rather similar to those for [PtCl₂(bu₂bpy)] (bu₂bpy is 4,4'-di-tert-butyl-2,2'-bipyridine), which has bulky substituents (Achor & Catalano, 1997), and [PtCl₂(i-biq)] (i-biq is 3,3'-biisoquinoline), which has an extended π-system (Kato et al., 1996), although both of them form columnar stacks.

The segregated packing of the paired coordination sites and the alkyl-chain layers strongly reflects the amphiphilic nature of (I). A similar layer structure was also reported for the crystals of [Pt(L)Cl] {HL is 4'-[4-(dodecyloxy)phenyl]-6'-phenyl-2,2'-bipyridine}, although this dagger-shaped complex takes a different arrangement from (I), which has the out-of-plane alkyl-chains (Neve et al., 1997).

The crystal structure of (I) suggests that the complex is appropriate for self-assembled systems on two-dimensional surfaces.

S2. Experimental

The dnbpy ligand was purchased from Aldrich. An acidic aqueous solution (20 ml) of K₂[PtCl₄] (103 mg, 0.25 mmol) and dnbpy (102 mg, 0.25 mmol) was heated at 343 K for 24 h to deposit a yellow product, (I) (yield 158 mg, 94%). Recrystallization from N,N-dimethylformamide gave yellow plate crystals. Analysis calculated for C₂₈H₄₄Cl₂N₂Pt: C 49.85, H 6.57, N 4.15%; found: C 49.90, H 6.45, N 4.30%. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 0.88 (s, 3H, CH₃), 1.28 (br, 12H, CH₂), 1.74 (br, 12H, CH₂), 2.79 (t, 2H, CH₂), 7.25 (d, 1H, bpy), 7.84 (s, 1H, bpy), 9.35 (d, 1H, bpy).

S3. Refinement

In the course of the refinement, one of alkyl chains showed extraordinarily large displacement parameters for atoms C26 and C27. These atoms were thus assigned two disordered positions. After refinement of the restrained occupancies, the final occupancies were fixed to 0.64 for C26 and C27, and 0.36 for C26' and C27', so that these atoms have similar values of U_eq. H atoms were treated as riding atoms, with C—H distances in the range 0.93–0.99 Å. Is this added text OK?

Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku Corporation, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare, 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are plotted at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The disordered atoms C26' and C27' are drawn with open bonds.
	Fig. 2. The packing structure of (I) viewed down the b axis.
	Fig. 3. The face-to-face arrangement of the paired [PtCl2(dnbpy)] complexes in the structure of (I).

(I)

Crystal data

[PtCl2(C28H44N2)]	F(000) = 1352.00
Mr = 674.66	Dx = 1.567 Mg m^−3 Dm = 1.52 (1) Mg m^−3 Dm measured by flotation in hexane/CCl4 at 294 K
Monoclinic, P21/a	Mo Kα radiation, λ = 0.7107 Å
a = 16.663 (2) Å	Cell parameters from 8757 reflections
b = 10.6209 (5) Å	θ = 3.0–27.5°
c = 17.652 (2) Å	µ = 5.09 mm^−1
β = 113.725 (4)°	T = 173 K
V = 2860.0 (4) Å^3	Plate, yellow
Z = 4	0.64 × 0.47 × 0.11 mm

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer	5860 reflections with I > 2σ(I)
ω scans	Rint = 0.041
Absorption correction: numerical (NUMABS; Higashi, 1999)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.126, Tmax = 0.695	h = −20→21
22444 measured reflections	k = −13→13
6472 independent reflections	l = −16→22

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.022P)^2 + 9.2477P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max = −0.009
S = 1.15	Δρmax = 3.39 e Å^−3
6472 reflections	Δρmin = −0.95 e Å^−3
319 parameters

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt1	0.63473 (1)	0.16242 (2)	0.54671 (1)	0.02687 (6)
Cl1	0.77327 (8)	0.0788 (1)	0.61051 (8)	0.0391 (3)
Cl2	0.66905 (9)	0.3095 (1)	0.65009 (9)	0.0453 (3)
N1	0.5949 (3)	0.0391 (3)	0.4522 (2)	0.0273 (8)
N2	0.5098 (3)	0.2196 (4)	0.4871 (2)	0.0280 (8)
C1	0.6455 (3)	−0.0483 (4)	0.4376 (3)	0.031 (1)
C2	0.6125 (3)	−0.1288 (5)	0.3708 (3)	0.033 (1)
C3	0.5250 (3)	−0.1229 (4)	0.3168 (3)	0.0304 (10)
C4	0.4732 (3)	−0.0323 (4)	0.3326 (3)	0.0272 (9)
C5	0.5091 (3)	0.0477 (4)	0.3997 (3)	0.0254 (9)
C6	0.4602 (3)	0.1472 (4)	0.4205 (3)	0.0252 (9)
C7	0.3713 (3)	0.1660 (4)	0.3801 (3)	0.0267 (9)
C8	0.3295 (3)	0.2623 (4)	0.4030 (3)	0.0300 (10)
C9	0.3817 (4)	0.3391 (4)	0.4679 (3)	0.034 (1)
C10	0.4705 (3)	0.3149 (4)	0.5090 (3)	0.033 (1)
C11	0.4886 (4)	−0.2083 (5)	0.2427 (3)	0.036 (1)
C12	0.5151 (4)	−0.1648 (4)	0.1734 (3)	0.034 (1)
C13	0.4847 (4)	−0.2526 (5)	0.0995 (3)	0.037 (1)
C14	0.5121 (4)	−0.2111 (5)	0.0314 (3)	0.038 (1)
C15	0.4876 (4)	−0.3033 (5)	−0.0404 (3)	0.039 (1)
C16	0.5125 (3)	−0.2614 (5)	−0.1100 (3)	0.035 (1)
C17	0.4943 (3)	−0.3589 (5)	−0.1777 (3)	0.036 (1)
C18	0.5130 (3)	−0.3176 (5)	−0.2509 (3)	0.034 (1)
C19	0.5075 (4)	−0.4236 (5)	−0.3103 (4)	0.048 (1)
C20	0.2324 (3)	0.2829 (5)	0.3604 (3)	0.034 (1)
C21	0.2077 (3)	0.3848 (5)	0.2936 (3)	0.035 (1)
C22	0.2334 (4)	0.3513 (5)	0.2227 (4)	0.040 (1)
C23	0.2112 (4)	0.4515 (6)	0.1563 (4)	0.044 (1)
C24	0.2412 (4)	0.4181 (7)	0.0887 (4)	0.060 (2)
C25	0.2218 (5)	0.5118 (9)	0.0204 (4)	0.078 (2)
C26	0.2564 (8)	0.441 (1)	−0.0438 (8)	0.058 (3)	0.64
C26'	0.268 (1)	0.532 (2)	−0.033 (1)	0.059 (5)	0.36
C27	0.2402 (7)	0.514 (1)	−0.1178 (6)	0.057 (2)	0.64
C27'	0.243 (2)	0.424 (2)	−0.092 (1)	0.060 (6)	0.36
C28	0.2796 (5)	0.4465 (10)	−0.1670 (5)	0.083 (3)
H1	0.7055	−0.0529	0.4746	0.0315*
H2	0.6507	−0.1883	0.3625	0.0332*
H3	0.4125	−0.0263	0.2964	0.0272*
H4	0.3387	0.1113	0.3356	0.0267*
H5	0.3568	0.4081	0.4845	0.0340*
H6	0.5044	0.3671	0.5543	0.0326*
H7	0.5104	−0.2915	0.2581	0.0357*
H8	0.4267	−0.2089	0.2220	0.0357*
H9	0.4899	−0.0849	0.1548	0.0341*
H10	0.5770	−0.1594	0.1947	0.0341*
H11	0.5095	−0.3339	0.1178	0.0371*
H12	0.4231	−0.2581	0.0772	0.0371*
H13	0.4851	−0.1325	0.0113	0.0382*
H14	0.5743	−0.2008	0.0551	0.0382*
H15	0.5161	−0.3813	−0.0204	0.0386*
H16	0.4260	−0.3152	−0.0632	0.0386*
H17	0.4800	−0.1878	−0.1333	0.0351*
H18	0.5732	−0.2432	−0.0866	0.0351*
H19	0.5294	−0.4307	−0.1540	0.0361*
H20	0.4341	−0.3811	−0.1977	0.0361*
H21	0.4720	−0.2541	−0.2803	0.0338*
H22	0.5707	−0.2830	−0.2308	0.0338*
H23	0.4498	−0.4582	−0.3321	0.0484*
H24	0.5204	−0.3926	−0.3548	0.0484*
H25	0.5484	−0.4879	−0.2822	0.0484*
H26	0.2059	0.2053	0.3338	0.0345*
H27	0.2096	0.3047	0.3995	0.0345*
H28	0.1461	0.3978	0.2727	0.0348*
H29	0.2370	0.4602	0.3193	0.0348*
H30	0.2947	0.3374	0.2446	0.0404*
H31	0.2034	0.2765	0.1975	0.0404*
H32	0.1498	0.4631	0.1316	0.0443*
H33	0.2391	0.5281	0.1811	0.0443*
H34	0.3035	0.4063	0.1144	0.0598*
H35	0.2145	0.3407	0.0652	0.0598*
H36	0.1635	0.4944	−0.0154	0.0780*
H37	0.2521	0.5891	0.0383	0.0780*
H38	0.3196	0.4266	−0.0121	0.0580*	0.64
H38'	0.2503	0.6084	−0.0608	0.0593*	0.36
H39	0.218	0.353	−0.067	0.0598*	0.64
H39'	0.3289	0.5296	−0.0015	0.0593*	0.36
H40	0.1795	0.5249	−0.1510	0.0565*	0.64
H40'	0.2636	0.3468	−0.0647	0.0598*	0.36
H41	0.2668	0.5971	−0.1058	0.0565*	0.64
H41'	0.1780	0.4179	−0.1178	0.0598*	0.36
H42	0.2521	0.3668	−0.1829	0.0999*
H43	0.2718	0.4941	−0.2151	0.0999*
H44	0.3405	0.4349	−0.1348	0.0999*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.0261 (1)	0.02640 (9)	0.0294 (1)	−0.00419 (7)	0.01258 (7)	0.00191 (7)
Cl1	0.0278 (6)	0.0388 (6)	0.0462 (7)	−0.0042 (5)	0.0101 (5)	0.0033 (5)
Cl2	0.0397 (7)	0.0479 (7)	0.0448 (7)	−0.0095 (6)	0.0134 (6)	−0.0142 (6)
N1	0.031 (2)	0.025 (2)	0.030 (2)	−0.002 (1)	0.016 (2)	0.003 (1)
N2	0.032 (2)	0.028 (2)	0.026 (2)	−0.001 (2)	0.014 (2)	0.000 (2)
C1	0.028 (2)	0.029 (2)	0.042 (3)	0.002 (2)	0.019 (2)	0.005 (2)
C2	0.034 (3)	0.033 (2)	0.037 (3)	0.005 (2)	0.019 (2)	0.001 (2)
C3	0.043 (3)	0.023 (2)	0.032 (2)	−0.003 (2)	0.022 (2)	0.004 (2)
C4	0.028 (2)	0.030 (2)	0.027 (2)	−0.001 (2)	0.015 (2)	0.003 (2)
C5	0.028 (2)	0.026 (2)	0.027 (2)	−0.001 (2)	0.015 (2)	0.005 (2)
C6	0.027 (2)	0.026 (2)	0.026 (2)	0.000 (2)	0.015 (2)	0.006 (2)
C7	0.028 (2)	0.024 (2)	0.031 (2)	−0.003 (2)	0.014 (2)	0.000 (2)
C8	0.032 (2)	0.034 (2)	0.031 (2)	0.003 (2)	0.021 (2)	0.005 (2)
C9	0.041 (3)	0.032 (2)	0.037 (3)	0.005 (2)	0.024 (2)	−0.001 (2)
C10	0.038 (3)	0.031 (2)	0.035 (3)	−0.001 (2)	0.020 (2)	−0.004 (2)
C11	0.045 (3)	0.029 (2)	0.036 (3)	−0.004 (2)	0.020 (2)	−0.003 (2)
C12	0.043 (3)	0.032 (2)	0.033 (3)	−0.002 (2)	0.021 (2)	−0.001 (2)
C13	0.044 (3)	0.034 (2)	0.037 (3)	−0.007 (2)	0.020 (2)	−0.007 (2)
C14	0.047 (3)	0.034 (2)	0.040 (3)	−0.003 (2)	0.023 (2)	−0.003 (2)
C15	0.039 (3)	0.042 (3)	0.039 (3)	−0.004 (2)	0.020 (2)	−0.003 (2)
C16	0.036 (3)	0.038 (3)	0.035 (3)	0.000 (2)	0.017 (2)	−0.002 (2)
C17	0.037 (3)	0.041 (3)	0.036 (3)	−0.005 (2)	0.021 (2)	0.000 (2)
C18	0.032 (2)	0.039 (3)	0.034 (3)	0.002 (2)	0.017 (2)	0.003 (2)
C19	0.072 (4)	0.038 (3)	0.048 (3)	−0.005 (3)	0.036 (3)	−0.002 (2)
C20	0.032 (3)	0.037 (3)	0.040 (3)	0.002 (2)	0.021 (2)	0.003 (2)
C21	0.028 (2)	0.034 (2)	0.042 (3)	0.002 (2)	0.014 (2)	0.000 (2)
C22	0.032 (3)	0.046 (3)	0.044 (3)	0.009 (2)	0.017 (2)	0.005 (2)
C23	0.039 (3)	0.051 (3)	0.042 (3)	0.003 (2)	0.015 (2)	0.004 (2)
C24	0.054 (4)	0.083 (5)	0.048 (4)	0.020 (4)	0.027 (3)	0.007 (3)
C25	0.057 (4)	0.138 (8)	0.043 (4)	−0.001 (5)	0.025 (3)	0.021 (4)
C26	0.066 (7)	0.069 (8)	0.047 (7)	0.012 (6)	0.030 (6)	0.015 (6)
C26'	0.10 (2)	0.039 (9)	0.06 (1)	−0.003 (9)	0.05 (1)	0.007 (8)
C27	0.051 (6)	0.071 (7)	0.045 (6)	−0.001 (5)	0.018 (4)	0.005 (5)
C27'	0.09 (2)	0.05 (1)	0.04 (1)	−0.03 (1)	0.04 (1)	−0.005 (10)
C28	0.060 (5)	0.130 (8)	0.068 (5)	−0.016 (5)	0.035 (4)	−0.030 (5)

Geometric parameters (Å, º)

Pt1—Cl1	2.301 (1)	C17—C18	1.512 (9)
Pt1—Cl2	2.293 (2)	C17—H19	0.948
Pt1—N1	2.012 (4)	C17—H20	0.950
Pt1—N2	2.012 (4)	C18—C19	1.516 (8)
N1—C1	1.347 (7)	C18—H21	0.951
N1—C5	1.359 (5)	C18—H22	0.955
N2—C6	1.369 (5)	C19—H23	0.953
N2—C10	1.344 (7)	C19—H24	0.953
C1—C2	1.379 (7)	C19—H25	0.951
C1—H1	0.950	C20—C21	1.528 (7)
C2—C3	1.387 (6)	C20—H26	0.963
C2—H2	0.949	C20—H27	0.943
C3—C4	1.393 (7)	C21—C22	1.521 (9)
C3—C11	1.505 (7)	C21—H28	0.951
C4—C5	1.383 (6)	C21—H29	0.952
C4—H3	0.957	C22—C23	1.514 (8)
C5—C6	1.469 (7)	C22—H30	0.947
C6—C7	1.375 (6)	C22—H31	0.948
C7—C8	1.387 (7)	C23—C24	1.51 (1)
C7—H4	0.952	C23—H32	0.945
C8—C9	1.390 (6)	C23—H33	0.952
C8—C20	1.500 (7)	C24—C25	1.49 (1)
C9—C10	1.385 (7)	C24—H34	0.960
C9—H5	0.946	C24—H35	0.947
C10—H6	0.950	C25—C26	1.65 (2)
C11—C12	1.529 (9)	C25—C26'	1.46 (3)
C11—H7	0.952	C25—H36	0.939
C11—H8	0.946	C25—H37	0.950
C12—C13	1.515 (7)	C26—C27	1.45 (2)
C12—H9	0.946	C26—H38	0.985
C12—H10	0.947	C26—H39	1.114
C13—C14	1.515 (9)	C26'—C27'	1.48 (3)
C13—H11	0.956	C26'—H38'	0.931
C13—H12	0.942	C26'—H39'	0.945
C14—C15	1.521 (8)	C27—C28	1.47 (2)
C14—H13	0.946	C27—H40	0.950
C14—H14	0.955	C27—H41	0.968
C15—C16	1.513 (9)	C27'—C28	1.69 (3)
C15—H15	0.949	C27'—H40'	0.946
C15—H16	0.949	C27'—H41'	0.990
C16—C17	1.517 (8)	C28—H42	0.950
C16—H17	0.946	C28—H43	0.950
C16—H18	0.945	C28—H44	0.950
Pt1···C4^i	3.574 (6)	C1···C8^i	3.509 (7)
Cl1···C2^ii	3.587 (5)	C1···C21^iii	3.559 (8)
Cl1···C7^i	3.594 (5)	C1···C7^i	3.568 (8)
N1···C6^i	3.386 (7)	C2···C10^i	3.562 (8)
N1···C7^i	3.534 (6)	C2···C21^iii	3.582 (8)
N2···C5^i	3.557 (6)	C2···C9^i	3.589 (8)
Cl1—Pt1—Cl2	89.64 (5)	H19—C17—H20	109.6
Cl1—Pt1—N1	94.9 (1)	C17—C18—C19	113.6 (5)
Cl1—Pt1—N2	174.8 (1)	C17—C18—H21	108.8
Cl2—Pt1—N1	175.4 (1)	C17—C18—H22	108.5
Cl2—Pt1—N2	94.9 (1)	C19—C18—H21	108.6
N1—Pt1—N2	80.6 (2)	C19—C18—H22	108.3
Pt1—N1—C1	125.8 (3)	H21—C18—H22	108.9
Pt1—N1—C5	115.3 (3)	C18—C19—H23	109.7
C1—N1—C5	118.9 (4)	C18—C19—H24	110.0
Pt1—N2—C6	114.8 (3)	C18—C19—H25	109.9
Pt1—N2—C10	126.7 (3)	H23—C19—H24	109.0
C6—N2—C10	118.3 (4)	H23—C19—H25	109.1
N1—C1—C2	121.8 (4)	H24—C19—H25	109.1
N1—C1—H1	118.0	C8—C20—C21	113.1 (5)
C2—C1—H1	120.2	C8—C20—H26	108.1
C1—C2—C3	120.4 (5)	C8—C20—H27	109.8
C1—C2—H2	118.9	C21—C20—H26	107.6
C3—C2—H2	120.6	C21—C20—H27	109.2
C2—C3—C4	117.3 (4)	H26—C20—H27	109.0
C2—C3—C11	120.9 (5)	C20—C21—C22	113.1 (4)
C4—C3—C11	121.7 (4)	C20—C21—H28	108.4
C3—C4—C5	120.5 (4)	C20—C21—H29	107.5
C3—C4—H3	119.1	C22—C21—H28	109.4
C5—C4—H3	120.5	C22—C21—H29	109.2
N1—C5—C4	121.1 (4)	H28—C21—H29	109.2
N1—C5—C6	114.5 (4)	C21—C22—C23	114.2 (5)
C4—C5—C6	124.4 (4)	C21—C22—H30	108.3
N2—C6—C5	114.5 (4)	C21—C22—H31	108.2
N2—C6—C7	121.1 (4)	C23—C22—H30	108.3
C5—C6—C7	124.3 (4)	C23—C22—H31	107.9
C6—C7—C8	121.2 (4)	H30—C22—H31	109.9
C6—C7—H4	118.5	C22—C23—C24	113.0 (5)
C8—C7—H4	120.3	C22—C23—H32	109.4
C7—C8—C9	116.8 (4)	C22—C23—H33	108.9
C7—C8—C20	121.9 (4)	C24—C23—H32	107.9
C9—C8—C20	121.3 (5)	C24—C23—H33	108.0
C8—C9—C10	120.4 (5)	H32—C23—H33	109.8
C8—C9—H5	120.2	C23—C24—C25	116.6 (7)
C10—C9—H5	119.4	C23—C24—H34	107.2
N2—C10—C9	122.0 (4)	C23—C24—H35	107.7
N2—C10—H6	119.3	C25—C24—H34	108.0
C9—C10—H6	118.6	C25—C24—H35	108.3
C3—C11—C12	111.7 (4)	H34—C24—H35	108.8
C3—C11—H7	109.7	C24—C25—C26	103.1 (8)
C3—C11—H8	109.6	C24—C25—C26'	128 (1)
C12—C11—H7	108.0	C24—C25—H36	104.0
C12—C11—H8	108.3	C24—C25—H37	113.2
H7—C11—H8	109.6	C26—C25—H36	90.0
C11—C12—C13	113.5 (4)	C26—C25—H37	109.8
C11—C12—H9	108.6	C26'—C25—H36	105.1
C11—C12—H10	108.7	C26'—C25—H37	75.0
C13—C12—H9	107.8	H36—C25—H37	131.4
C13—C12—H10	108.2	C25—C26—C27	112 (1)
H9—C12—H10	110.1	C25—C26—H38	105.6
C12—C13—C14	113.7 (4)	C25—C26—H39	109.3
C12—C13—H11	108.4	C27—C26—H38	111.2
C12—C13—H12	109.2	C27—C26—H39	104.4
C14—C13—H11	107.6	H38—C26—H39	114.1
C14—C13—H12	108.2	C25—C26'—C27'	105 (1)
H11—C13—H12	109.6	C25—C26'—H38'	109.3
C13—C14—C15	114.1 (5)	C25—C26'—H39'	109.3
C13—C14—H13	107.7	C27'—C26'—H38'	111.9
C13—C14—H14	107.8	C27'—C26'—H39'	109.3
C15—C14—H13	109.2	H38'—C26'—H39'	111.6
C15—C14—H14	108.7	C26—C27—C28	107 (1)
H13—C14—H14	109.4	C26—C27—H40	112.6
C14—C15—C16	114.7 (5)	C26—C27—H41	113.0
C14—C15—H15	109.1	C28—C27—H40	108.1
C14—C15—H16	108.8	C28—C27—H41	107.4
C16—C15—H15	107.3	H40—C27—H41	108.0
C16—C15—H16	107.3	C26'—C27'—C28	110 (1)
H15—C15—H16	109.6	C26'—C27'—H40'	112.3
C15—C16—C17	113.9 (4)	C26'—C27'—H41'	109.1
C15—C16—H17	107.4	C28—C27'—H40'	109.9
C15—C16—H18	107.5	C28—C27'—H41'	108.4
C17—C16—H17	108.9	H40'—C27'—H41'	106.5
C17—C16—H18	108.9	C27—C28—H42	109.5
H17—C16—H18	110.2	C27—C28—H43	109.5
C16—C17—C18	115.5 (4)	C27—C28—H44	109.5
C16—C17—H19	108.0	H42—C28—H43	109.5
C16—C17—H20	108.1	H42—C28—H44	109.5
C18—C17—H19	107.9	H43—C28—H44	109.5
C18—C17—H20	107.7

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1; (iii) x+1/2, −y+1/2, z.