2,6-Bis­[2,4-bis­(heptyl­oxy)­phenyl]­pyridine

Alcock, N.W.; Rourke, J.P.

doi:10.1107/S1600536805001248

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 2| February 2005| Pages o368-o369

https://doi.org/10.1107/S1600536805001248

2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine

Nathaniel W. Alcock ^a ^* and Jonathan P Rourke ^a

^aDepartment of Chemistry, University of Warwick, Coventry CV4 7AL, England
^*Correspondence e-mail: n.w.alcock@warwick.ac.uk

(Received 16 December 2004; accepted 13 January 2005; online 22 January 2005)

The title 2,6-disubstituted pyridine, C₄₁H₆₁NO₄, with a crystallographic twofold axis, has an arrangement of molecules well organized to undergo multiple cyclometallation reactions.

Comment

2,6-Disubstituted pyridines are ideally set up to undergo multiple cyclometallations, reactions of considerable interest to us (Cave et al., 1999 , 2000 ). In addition to their ability to undergo multiple cyclometallations, such compounds have also been shown to be activated by other reagents (Cave et al., 1998 ).

The title molecule, (I) (Fig. 1), has crystallographic twofold symmetry and the aliphatic chains are each in an extended form. Within the unit cell, the molecules are aligned in an antiparallel fashion (Figs. 2 and 3).

Figure 1
View of the title molecule, showing the atomic numbering. Displacement ellipsoids are drawn at the 50% probability level. Both disorder components are shown in all Figures.

Figure 2
Packing diagram of (I

), viewed down the a axis. H atoms have been omitted.

Figure 3
Packing diagram of (I

), viewed down the b axis. H atoms have been omitted.

Experimental

1-Chloro-2,4-bis(heptyloxy)benzene (15.0 g, 48.0 mmol) was added dropwise to a stirred solution of magnesium (1.22 g, 50.0 mmol) and methyl iodide (0.30 g, 2.11 mmol) in tetrahydrofuran (THF, 25 ml) under an inert atmosphere. The resulting Grignard reagent was transferred via a cannula to a stirred solution of 2,6-dichloropyridine (2.96 g, 20.0 mmol) and tetrakis(triphenylphosphine)palladium (0.45 g, 0.50 mmol) in THF (25 ml). The reaction mixture was then heated under reflux (24 h) under an inert atmosphere. Excess Grignard was destroyed with water (20 ml) and hydrochloric acid (5 ml, 2 M). The neutralized (aqueous NaOH) reaction mixture was extracted with diethyl ether (2 × 200 ml) and dried (saturated NaCl and magnesium sulfate). The solvent was removed under vacuum and the product crystallized out as white needle-like crystals (yield: 12.0 g, 19.0 mmol, 95%). ¹H NMR (CDCl₃, 250.13 MHz): δ 7.96 (2H, d, ³J = 8.5 Hz), 7.75 (2H, d, ³J = 7.3 Hz), 7.60 (1H, t, ³J = 7.3 Hz), 6.59 (2H, dd, ³J = 8.5, ⁴J = 2.1 Hz), 6.53 (2H, d, ⁴J = 2.1 Hz), 3.99 (8H, t, ³J = 6.7 Hz), 1.79 (8H, m), 1.48 (24H, m), 0.89 (12H, m). ¹³C NMR (CDCl₃, 250.13 MHz): δ 160.5, 157.7, 154.7, 134.8, 132.1, 131.5, 121.9, 105.6, 100.0, 68.2, 31.4, 25.7, 22.5. Elemental analysis found (expected): C 77.8 (77.9), H 9.6 (9.7), N 2.4% (2.2%).

Crystal data

C₄₁H₆₁NO₄
M_r = 631.91
Monoclinic, P2/n
a = 11.2502 (10) Å
b = 6.9682 (6) Å
c = 24.014 (2) Å
β = 93.963 (2)°
V = 1878.0 (3) Å³
Z = 2
D_x = 1.117 Mg m⁻³
Mo Kα radiation
Cell parameters from 2201 reflections
θ = 3–15°
μ = 0.07 mm⁻¹
T = 180 (2) K
Block, colourless
0.45 × 0.25 × 0.20 mm

Data collection

Bruker SMART diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.896, T_max = 0.989
8996 measured reflections
3318 independent reflections
1753 reflections with I > 2σ(I)
R_int = 0.045
θ_max = 25.0°
h = −13 → 13
k = −8 → 7
l = −18 → 28

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.168
S = 1.04
3318 reflections
229 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.078P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.043
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

H atoms were added at calculated positions (C—H = 0.95–0.99 Å) and refined using a riding model (including free rotation about C—C bonds for methyl groups), with U_iso(H) = 1.2 (or 1.5 for methyl H atoms) times U_eq(C). The terminal section of one of the heptane chains was found to be disordered between two positions [relative occupancies 0.43 (1):0.57 (1)]. This disorder is believed to be responsible for various anomalies in the displacement parameters of the atoms in this region of the molecule.

Data collection: SMART (Siemens, 1994 ); cell refinement: SAINT (Siemens, 1995 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805001248/tk6205sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805001248/tk6205Isup2.hkl

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine top

Crystal data top

C₄₁H₆₁NO₄	F(000) = 692
M_r = 631.91	D_x = 1.117 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 2201 reflections
a = 11.2502 (10) Å	θ = 3–15°
b = 6.9682 (6) Å	µ = 0.07 mm⁻¹
c = 24.014 (2) Å	T = 180 K
β = 93.963 (2)°	Block, colourless
V = 1878.0 (3) Å³	0.45 × 0.25 × 0.2 mm
Z = 2

Data collection top

Siemens SMART diffractometer	3318 independent reflections
Radiation source: fine-focus sealed tube	1753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→7
T_min = 0.896, T_max = 0.989	l = −18→28
8996 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.078P)²] where P = (F_o² + 2F_c²)/3
3318 reflections	(Δ/σ)_max = 0.043
229 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

Experimental. The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures with different φ angles for the crystal; each 10 s exposure covered 0.3° in ω. The crystal-to-detector distance was 5.0 cm. Coverage of the unique set is over 97% complete to at least 26° in θ. Crystal decay was found to be negligible by by repeating the initial frames at data collection and analyzing the duplicate reflections.

Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.27150 (17)	0.9445 (3)	0.49155 (7)	0.0557 (6)
O2	0.12875 (16)	0.3876 (2)	0.39451 (7)	0.0541 (6)
C01	0.2706 (2)	0.8380 (4)	0.44357 (10)	0.0443 (7)
C02	0.2012 (2)	0.6730 (4)	0.44313 (10)	0.0451 (7)
H02A	0.1582	0.6425	0.4746	0.054*
C03	0.1942 (2)	0.5526 (4)	0.39711 (10)	0.0422 (7)
C04	0.2560 (2)	0.5969 (3)	0.34979 (9)	0.0366 (6)
C05	0.3235 (2)	0.7629 (4)	0.35173 (10)	0.0413 (7)
H05A	0.3653	0.7958	0.3200	0.050*
C06	0.3333 (2)	0.8842 (4)	0.39782 (10)	0.0437 (7)
H06A	0.3818	0.9958	0.3979	0.052*
C07	0.2497 (2)	0.4772 (4)	0.29833 (10)	0.0372 (6)
N08	0.2500	0.5760 (4)	0.2500	0.0376 (7)
C009	0.2482 (2)	0.2775 (4)	0.29932 (11)	0.0435 (7)
H09A	0.2460	0.2110	0.3338	0.052*
C010	0.2500	0.1771 (5)	0.2500	0.0430 (9)
H01C	0.2500	0.0408	0.2500	0.052*
C11	0.3361 (2)	1.1221 (4)	0.49299 (10)	0.0492 (7)
H11A	0.3040	1.2079	0.4627	0.059*
H11B	0.4214	1.0980	0.4877	0.059*
C12	0.3225 (3)	1.2141 (4)	0.54911 (10)	0.0535 (8)
H12A	0.3514	1.1239	0.5789	0.064*
H12B	0.2371	1.2390	0.5535	0.064*
C13	0.3912 (2)	1.4015 (4)	0.55598 (11)	0.0490 (7)
H13A	0.4766	1.3763	0.5515	0.059*
H13B	0.3623	1.4913	0.5261	0.059*
C14	0.3784 (2)	1.4954 (4)	0.61216 (11)	0.0540 (8)
H14A	0.2927	1.5150	0.6172	0.065*
H14B	0.4102	1.4071	0.6419	0.065*
C15	0.4417 (3)	1.6856 (4)	0.61915 (12)	0.0585 (8)
H15A	0.4093	1.7744	0.5897	0.070*
H15B	0.5273	1.6663	0.6136	0.070*
C16	0.4301 (3)	1.7785 (5)	0.67574 (13)	0.0759 (10)
H16A	0.4709	1.9028	0.6769	0.114*
H16B	0.4663	1.6951	0.7051	0.114*
H16C	0.3456	1.7975	0.6817	0.114*
C21	0.0420 (3)	0.3509 (4)	0.43410 (13)	0.0642 (9)
H21A	−0.0202	0.4517	0.4321	0.077*
H21B	0.0800	0.3472	0.4725	0.077*
C22	−0.0114 (4)	0.1576 (5)	0.41802 (17)	0.0954 (14)
H22A	0.0528	0.0602	0.4208	0.114*
H22B	−0.0697	0.1228	0.4454	0.114*
C23	−0.0705 (4)	0.1487 (7)	0.3625 (2)	0.145 (2)
H23A	−0.0256	0.2193	0.3350	0.174*	0.554 (17)
H23B	−0.1530	0.1988	0.3618	0.174*	0.554 (17)
H23C	−0.0142	0.2079	0.3376	0.174*	0.446 (17)
H23D	−0.1383	0.2389	0.3635	0.174*	0.446 (17)
C24A	−0.0681 (14)	−0.0784 (13)	0.3520 (6)	0.112 (6)	0.554 (17)
H24A	0.0098	−0.1248	0.3684	0.134*	0.554 (17)
H24B	−0.1295	−0.1346	0.3747	0.134*	0.554 (17)
C25A	−0.083 (2)	−0.152 (2)	0.3054 (8)	0.181 (8)	0.554 (17)
H25A	−0.0297	−0.0728	0.2833	0.218*	0.554 (17)
H25B	−0.1643	−0.1095	0.2931	0.218*	0.554 (17)
C24B	−0.1284 (9)	−0.0165 (13)	0.3271 (5)	0.070 (4)	0.446 (17)
H24C	−0.1757	0.0331	0.2939	0.084*	0.446 (17)
H24D	−0.1801	−0.0969	0.3494	0.084*	0.446 (17)
C25B	−0.0166 (9)	−0.130 (2)	0.3104 (5)	0.066 (4)	0.446 (17)
H25C	0.0368	−0.1626	0.3435	0.079*	0.446 (17)
H25D	0.0287	−0.0562	0.2837	0.079*	0.446 (17)
C26	−0.0762 (4)	−0.3254 (7)	0.28082 (17)	0.1204 (16)
H26A	−0.1069	−0.3160	0.2417	0.181*	0.554 (17)
H26B	−0.1240	−0.4180	0.3003	0.181*	0.554 (17)
H26C	0.0070	−0.3682	0.2826	0.181*	0.554 (17)
H26D	−0.0117	−0.4042	0.2676	0.181*	0.446 (17)
H26E	−0.1300	−0.2868	0.2490	0.181*	0.446 (17)
H26F	−0.1206	−0.3997	0.3071	0.181*	0.446 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0802 (15)	0.0520 (13)	0.0360 (11)	−0.0067 (10)	0.0114 (10)	−0.0088 (9)
O2	0.0646 (13)	0.0517 (12)	0.0484 (12)	−0.0118 (10)	0.0215 (9)	−0.0057 (10)
C01	0.0566 (18)	0.0463 (17)	0.0298 (15)	0.0079 (14)	0.0023 (13)	−0.0010 (13)
C02	0.0545 (18)	0.0496 (18)	0.0325 (16)	0.0021 (14)	0.0121 (12)	0.0044 (13)
C03	0.0490 (17)	0.0400 (16)	0.0381 (16)	0.0025 (13)	0.0069 (12)	0.0017 (13)
C04	0.0443 (15)	0.0355 (15)	0.0300 (14)	0.0073 (12)	0.0027 (11)	0.0010 (12)
C05	0.0516 (17)	0.0407 (16)	0.0320 (15)	0.0033 (13)	0.0068 (12)	0.0039 (12)
C06	0.0567 (18)	0.0376 (15)	0.0367 (16)	0.0009 (13)	0.0034 (13)	0.0012 (13)
C07	0.0373 (15)	0.0392 (16)	0.0355 (15)	0.0032 (12)	0.0062 (12)	0.0023 (12)
N08	0.0451 (18)	0.0372 (18)	0.0307 (17)	0.000	0.0040 (13)	0.000
C009	0.0495 (17)	0.0416 (17)	0.0400 (16)	0.0034 (13)	0.0071 (12)	0.0048 (13)
C010	0.051 (2)	0.032 (2)	0.046 (2)	0.000	0.0066 (18)	0.000
C11	0.0569 (18)	0.0506 (18)	0.0400 (16)	0.0015 (14)	0.0017 (13)	−0.0064 (14)
C12	0.066 (2)	0.0540 (19)	0.0406 (17)	−0.0002 (15)	0.0045 (14)	−0.0038 (14)
C13	0.0570 (18)	0.0502 (18)	0.0398 (16)	0.0056 (14)	0.0023 (13)	−0.0041 (14)
C14	0.0570 (19)	0.0567 (19)	0.0489 (18)	−0.0020 (15)	0.0077 (14)	−0.0110 (15)
C15	0.063 (2)	0.0550 (19)	0.057 (2)	0.0009 (15)	−0.0013 (15)	−0.0082 (15)
C16	0.072 (2)	0.080 (2)	0.076 (2)	−0.0088 (18)	0.0062 (18)	−0.0286 (19)
C21	0.067 (2)	0.066 (2)	0.063 (2)	−0.0104 (16)	0.0337 (16)	−0.0064 (17)
C22	0.095 (3)	0.082 (3)	0.118 (3)	−0.030 (2)	0.063 (3)	−0.014 (3)
C23	0.106 (4)	0.144 (5)	0.185 (6)	−0.057 (3)	0.012 (4)	−0.065 (4)
C24A	0.114 (10)	0.104 (9)	0.121 (11)	−0.043 (7)	0.042 (8)	−0.054 (7)
C25A	0.22 (2)	0.102 (10)	0.23 (2)	−0.045 (14)	0.080 (17)	−0.060 (10)
C24B	0.044 (6)	0.068 (6)	0.094 (8)	0.012 (4)	−0.018 (4)	0.002 (5)
C25B	0.049 (6)	0.086 (8)	0.064 (6)	0.004 (5)	0.011 (4)	0.003 (5)
C26	0.141 (4)	0.122 (4)	0.099 (3)	0.044 (3)	0.018 (3)	−0.030 (3)

Geometric parameters (Å, º) top

O1—C01	1.370 (3)	C15—H15B	0.9900
O1—C11	1.434 (3)	C16—H16A	0.9800
O2—C03	1.364 (3)	C16—H16B	0.9800
O2—C21	1.432 (3)	C16—H16C	0.9800
C01—C06	1.384 (3)	C21—C22	1.514 (4)
C01—C02	1.390 (3)	C21—H21A	0.9900
C02—C03	1.385 (3)	C21—H21B	0.9900
C02—H02A	0.9500	C22—C23	1.450 (6)
C03—C04	1.407 (3)	C22—H22A	0.9900
C04—C05	1.382 (3)	C22—H22B	0.9900
C04—C07	1.489 (3)	C23—C24B	1.547 (8)
C05—C06	1.391 (3)	C23—C24A	1.603 (8)
C05—H05A	0.9500	C23—H23A	0.9900
C06—H06A	0.9500	C23—H23B	0.9900
C07—N08	1.350 (3)	C23—H23C	0.9900
C07—C009	1.392 (3)	C23—H23D	0.9899
N08—C07ⁱ	1.350 (3)	C24A—C25A	1.23 (2)
C009—C010	1.377 (3)	C24A—H24A	0.9900
C009—H09A	0.9500	C24A—H24B	0.9900
C010—C009ⁱ	1.377 (3)	C25A—C26	1.352 (16)
C010—H01C	0.9500	C25A—H25A	0.9900
C11—C12	1.509 (3)	C25A—H25B	0.9900
C11—H11A	0.9900	C24B—C25B	1.563 (18)
C11—H11B	0.9900	C24B—H24C	0.9900
C12—C13	1.520 (4)	C24B—H24D	0.9900
C12—H12A	0.9900	C25B—C26	1.654 (16)
C12—H12B	0.9900	C25B—H25C	0.9900
C13—C14	1.515 (3)	C25B—H25D	0.9900
C13—H13A	0.9900	C26—H26A	0.9800
C13—H13B	0.9900	C26—H26B	0.9800
C14—C15	1.508 (3)	C26—H26C	0.9800
C14—H14A	0.9900	C26—H26D	0.9800
C14—H14B	0.9900	C26—H26E	0.9799
C15—C16	1.519 (4)	C26—H26F	0.9800
C15—H15A	0.9900

C01—O1—C11	117.5 (2)	H16B—C16—H16C	109.5
C03—O2—C21	120.7 (2)	O2—C21—C22	105.5 (2)
O1—C01—C06	124.5 (2)	O2—C21—H21A	110.7
O1—C01—C02	115.2 (2)	C22—C21—H21A	110.7
C06—C01—C02	120.2 (2)	O2—C21—H21B	110.7
C03—C02—C01	120.5 (2)	C22—C21—H21B	110.7
C03—C02—H02A	119.7	H21A—C21—H21B	108.8
C01—C02—H02A	119.7	C23—C22—C21	114.9 (4)
O2—C03—C02	123.2 (2)	C23—C22—H22A	108.5
O2—C03—C04	116.3 (2)	C21—C22—H22A	108.5
C02—C03—C04	120.5 (2)	C23—C22—H22B	108.5
C05—C04—C03	117.2 (2)	C21—C22—H22B	108.5
C05—C04—C07	119.4 (2)	H22A—C22—H22B	107.5
C03—C04—C07	123.3 (2)	C22—C23—C24B	133.3 (6)
C04—C05—C06	123.3 (2)	C22—C23—C24A	100.1 (7)
C04—C05—H05A	118.4	C22—C23—H23A	111.8
C06—C05—H05A	118.4	C24B—C23—H23A	102.6
C01—C06—C05	118.3 (2)	C24A—C23—H23A	111.8
C01—C06—H06A	120.9	C22—C23—H23B	111.8
C05—C06—H06A	120.9	C24B—C23—H23B	83.9
N08—C07—C009	121.7 (2)	C24A—C23—H23B	111.7
N08—C07—C04	115.1 (2)	H23A—C23—H23B	109.5
C009—C07—C04	123.1 (2)	C22—C23—H23C	105.4
C07ⁱ—N08—C07	118.6 (3)	C24B—C23—H23C	104.0
C010—C009—C07	119.5 (3)	C24A—C23—H23C	107.3
C010—C009—H09A	120.3	H23B—C23—H23C	118.7
C07—C009—H09A	120.3	C22—C23—H23D	104.8
C009—C010—C009ⁱ	119.0 (3)	C24B—C23—H23D	100.9
C009—C010—H01C	120.5	C24A—C23—H23D	130.7
C009ⁱ—C010—H01C	120.5	H23C—C23—H23D	106.1
O1—C11—C12	107.8 (2)	C25A—C24A—C23	123.3 (15)
O1—C11—H11A	110.2	C25A—C24A—H24A	106.5
C12—C11—H11A	110.2	C23—C24A—H24A	106.5
O1—C11—H11B	110.2	C25A—C24A—H24B	106.5
C12—C11—H11B	110.2	C23—C24A—H24B	106.5
H11A—C11—H11B	108.5	H24A—C24A—H24B	106.5
C11—C12—C13	112.3 (2)	C24A—C25A—C26	139.6 (19)
C11—C12—H12A	109.1	C24A—C25A—H25A	102.2
C13—C12—H12A	109.1	C26—C25A—H25A	102.2
C11—C12—H12B	109.1	C24A—C25A—H25B	102.1
C13—C12—H12B	109.1	C26—C25A—H25B	102.2
H12A—C12—H12B	107.9	H25A—C25A—H25B	104.8
C14—C13—C12	112.9 (2)	C23—C24B—C25B	101.7 (9)
C14—C13—H13A	109.0	C23—C24B—H24C	111.4
C12—C13—H13A	109.0	C25B—C24B—H24C	111.4
C14—C13—H13B	109.0	C23—C24B—H24D	111.4
C12—C13—H13B	109.0	C25B—C24B—H24D	111.4
H13A—C13—H13B	107.8	C24B—C25B—C26	102.6 (7)
C15—C14—C13	113.9 (2)	C24B—C25B—H25D	111.3
C15—C14—H14A	108.8	C26—C25B—H25D	111.3
C13—C14—H14A	108.8	C25A—C26—H26A	109.5
C15—C14—H14B	108.8	C25B—C26—H26A	117.5
C13—C14—H14B	108.8	C25A—C26—H26B	109.5
H14A—C14—H14B	107.7	C25B—C26—H26B	123.8
C14—C15—C16	113.9 (2)	H26A—C26—H26B	109.5
C14—C15—H15A	108.8	C25A—C26—H26C	109.4
C16—C15—H15A	108.8	C25B—C26—H26C	82.7
C14—C15—H15B	108.8	H26A—C26—H26C	109.5
C16—C15—H15B	108.8	H26B—C26—H26C	109.5
H15A—C15—H15B	107.7	C25B—C26—H26D	108.2
C15—C16—H16A	109.5	C25B—C26—H26E	108.6
C15—C16—H16B	109.5	H26D—C26—H26E	109.5
H16A—C16—H16B	109.5	C25B—C26—H26F	111.6
C15—C16—H16C	109.5	H26D—C26—H26F	109.5
H16A—C16—H16C	109.5	H26E—C26—H26F	109.5

Symmetry code: (i) −x+1/2, y, −z+1/2.

Acknowledgements

The EPSRC and Siemens generously supported the purchase of the SMART diffractometer.

References

Cave, G. W. V., Alcock, N. W. & Rourke, J. P. (1999). Organometallics, 18, 1801–1803. Web of Science CSD CrossRef CAS Google Scholar
Cave, G. W. V., Fanizzi, F. P., Deeth, R. J., Errington, W. & Rourke, J. P. (2000). Organometallics, 19, 1355–1364. Web of Science CSD CrossRef CAS Google Scholar
Cave, G. W. V., Hallett, A. J., Errington, W. & Rourke, J. P. (1998). Angew. Chem. Int. Ed. 37, 3270–3272. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1994). SMART. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1995). SAINT. Version 4. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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