Di-tert-butyl ketone hydrazone and di-tert-butyl ketone triphenyl­phosphoranyl­idene­hydrazone

Reaction of di-tert-butyl ketone with hydrazine hydrate gives di-tert-butyl ketone hydrazone, C₉H₂₀N₂, which is dimerized by double hydrogen bonding in the solid state. Further reaction of this compound with dibromo­triphenyl­phospho­rane gives di-tert-butyl ketone triphenyl­phosphoranyl­idene­hydrazone, C₂₇H₃₃N₂P, in the structure of which double chains parallel to the c axis are formed through weak C—H...π and π–π stacking inter­actions. The hydrazone group is nearly planar in both cases. In the second compound, one of the aromatic rings is nearly coplanar with the hydrazone moiety, indicating possible π-conjugation.

S1. Comment

To date, the highly sterically crowded alkene tetra-tert-butylethylene has not been synthesized, in spite of many attempts using various methods, such as the McMurry coupling reaction (Ephritikhine & Villiers, 2004), Barton's extrusion process (Barton et al., 1974) and reactions exploiting other possible pathways (Sulzbach et al., 1996). During our investigations into the McMurry reaction, we have particularly studied the carbonyl coupling of benzophenone and di-tert-butyl ketone with the MCl₄/M'(Hg) system (M/M' = U/Na, U/Li or Ti/Li) (Ephritikhine & Villiers, 2004). During this work, we have prepared di-tert-butyl ketone hydrazone, (I), and the new compound di-tert-butyl ketone (triphenylphosphorane)hydrazone, (II), by analogy with the synthesis reported for the two corresponding benzophenone derivatives (Barton et al., 1974; Bestmann & Fritzsche, 1961). The crystal structure of benzophenone (triphenylphosphorane)hydrazone, (III), has been reported previously (Bethell et al., 1992). Compound (II) could not be transformed into tetra-tert-butylethylene.

The asymmetric unit in (I) contains one hydrazone molecule. The C1═N2 and N1—N2 bond lengths (Table 1) are in agreement with the mean values reported for similar hydrazones in the Cambridge Structural Database (CSD, Version 5.27; Allen, 2002), which are 1.282 (11) and 1.38 (3) Å, respectively. The C1—C2 and C1—C6 bond lengths and the C2—C1—C6 angle are also in agreement with the mean values for similar di-^tBu-substituted sp²-hybridized C atoms reported in the CSD, which are 1.56 (5) Å and 123 (3)°. The value of the N2—C1—C6 angle is lower by about 11° than those of the other two angles around C1, which is likely due to the minimal crowding in the corresponding sector, atom N1 being on the same side as C2. The five atoms N1, N2, C1, C2 and C6 define a plane with an r.m.s. deviation of 0.005 Å. Centrosymmetric dimers are formed through double hydrogen bonding between the N—NH₂ groups of two neighbouring molecules, with the formation of a six-membered ring (Fig. 1 and Table 2).

The asymmetric unit in (II) contains two independent but nearly identical molecules, denoted A and B (molecule A is represented in Fig. 2). These two molecules fit to one another with an overall r.m.s. of 0.143 Å (the largest deviations, up to 0.29 Å, are those of atoms in the ^tBu groups and aromatic rings) (OFIT in SHELXTL; Bruker, 1999). The C1═N2 bond lengths [Table 3; mean value 1.2905 (15) Å], as well as the angles around C1, match those in (I), but the N1—N2 distances [mean value 1.4205 (5) Å] are slightly larger than those in compounds (I) and (III) [1.388 (4) Å] and are also larger than the mean value for N—N bond lengths in (triphenylphosphorane)hydrazone C═N—N═P(C₆H₅)₃ groups reported in the CSD [1.384 (19) Å]. This may be due to the crowding induced by the simultaneous presence of ^tBu groups and aromatic rings in (II). However, the mean P1═N1 bond length of 1.6017 (9) Å is slightly lower than the mean value of 1.616 (13) Å from the CSD and the value of 1.606 (3) Å in (III). These bond lengths indicate the presence of double bonds between C1 and N2 and between P1 and N1. However, their slight deviation from the values tabulated for single and double bonds has been considered as possible evidence of π-conjugation over the whole of the (triphenylphosphorane)hydrazone moiety (Bethell et al., 1992). This moiety adopts a trans geometry with respect to the central N1—N2 bond in (II), as is usual in such compounds (Bethell et al., 1992; Minutolo et al., 1999).

The group defined by the atoms P1, N1, N2, C1, C2 and C6 is close to planarity in both molecules of (II), with r.m.s. deviations of 0.010 and 0.024 Å and P1—N1—N2—C1 torsion angles of 179.55 (14) and 175.93 (14)° in molecules A and B, respectively. One of the aromatic rings in both molecules (atoms C10–C15) is nearly coplanar with the (triphenylphosphorane)hydrazone mean plane, with dihedral angles of 8.70 (12) and 2.78 (12)° in molecules A and B, respectively (but with, however, out-of-plane displacements as large as 0.4 Å). Such a geometry has previously been observed in a related (triphenylphosphorane)hydrazone compound, (2,4-cyclopentadien-1-ylidenehydrazono)triphenylphosphorane, (IV), and considered as indicative of the possibility of π-conjugation between the two fragments, which was supported by the corresponding P—C bond length being slightly smaller that those of the other two, by about 0.011 Å (Minutolo et al., 1999).

The P1—C10 bonds in (II) are also slightly shorter than P1—C16 and P1—C22, by about 0.01–0.02 Å, which confirms the previous observation. However, the C—N, N—N, P—N and P—C bonds in (II) are all longer, by 0.01–0.05 Å, than their counterparts in (IV) (the largest difference corresponds to N—N), which may partly be due to the data collection temperature difference of 98 K, but also to the presence in (IV) of a Cp ring instead of the two ^tBu groups in (II), with possible additional conjugation effects. The aromatic C—C bond lengths in (II) are in the usual range in all three rings.

The aromatic rings in (II) are involved in several weak intermolecular interactions. π–π stacking interactions are possibly present between the rings C10–C15 (centroid Cg1) and C16–C21 (centroid Cg2) of molecules related by a glide plane, for both A and B molecules [Cg1A···Cg2Aⁱ = 3.76 Å, dihedral angle 7.0°, centroid offset 1.65 Å and shortest interatomic contact 3.26 Å for A molecules; Cg1B···Cg2Bⁱ 3.64 Å, dihedral angle 6.5°, centroid offset 1.22 Å and shortest interatomic contact 3.36 Å for B molecules; symmetry code: (i) x, 3/2 − y, z − 1/2]. Although the shortest interatomic contacts are shorter than twice the out-of-plane van der Waals radius of C (1.7 Å; Reference?), these interactions are weak at best, due to the large offset values.

Three significant C—H···π interactions are also present. One of them links molecules A and B in the asymmetric unit [H13A···Cg1B = 2.74 Å and C13A—H13A···Cg1B = 153°] and the other two involve two sets of adjacent A or B molecules [H20A···Cg3Aⁱⁱ = 2.68 Å and C20A—H20A···Cg3Aⁱⁱ = 154°; H20B···Cg3Bⁱⁱ = 2.60 Å and C20B—H20B···Cg3Bⁱⁱ = 147°; Cg3 is the centroid of the C22–C27 ring; symmetry code: (ii) x, 3/2 − y, z + 1/2]. Molecule A thus acts as a hydrogen-bond donor to two neighbouring molecules and as an acceptor from one, whereas molecule B acts as a single donor and double acceptor. These interactions result in double chains of A and B molecules running along the c axis (Fig. 3).

S2. Experimental

Reaction of di-tert-butyl ketone with hydrazine hydrate in diethylene glycol gave compound (I) in 94% yield. [Please give brief details of quantities used] The ¹H NMR spectrum of (I) in CDCl₃ is identical to that previously described (Hartzler, 1971). Reaction of (I) with dibromotriphenylphosphorane gave compound (II) in 60% yield. [Please give brief details of quantities used] ¹H NMR (200 MHz, CDCl₃, δ, p.p.m.): 1.08 (s, 9H, ^tBu), 1.56 (s, 9H, ^tBu), 7.33–7.51 (m, 9H, ortho- and para-Ph₃P), 7.61–7.74 (m, 6H, meta-Ph₃P). Single crystals of both compounds were obtained by slow evaporation of pentane solutions.

S3. Refinement

The two H atoms bound to N1 in (I) were found in a difference Fourier map and they were refined with U_iso(H) = 1.2U_eq(N1). All other H atoms in both compounds were introduced at calculated positions as riding atoms, with C—H bond lengths of 0.93 (aromatic CH) or 0.96 Å (CH₃), and with U_iso(H) = 1.2U_eq(CH) or 1.5U_eq(CH₃).

Computing details

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. A view of (I), with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are related by the symmetry operator (−x, −y, −z).
	Fig. 2. A view of molecule A in (II). with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. A view of (II), showing the double chains along the c axis. C—H···π and π–π stacking interactions are represented as dashed and dotted lines, respectively. Displacement ellipsoids are drawn at the 30% probability level.

(I) Di-tert-butyl ketone hydrazone

Crystal data

C9H20N2	F(000) = 352
Mr = 156.27	Dx = 1.040 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23020 reflections
a = 11.5299 (8) Å	θ = 3.1–25.7°
b = 8.0975 (4) Å	µ = 0.06 mm^−1
c = 10.8937 (8) Å	T = 100 K
β = 101.111 (3)°	Irregular, colourless
V = 998.01 (11) Å^3	0.23 × 0.19 × 0.16 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	1717 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.7°, θmin = 3.1°
two ϕ and two ω scans with 2° steps	h = −14→13
23020 measured reflections	k = −9→0
1884 independent reflections	l = 0→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.3197P] where P = (Fo^2 + 2Fc^2)/3
1884 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. crystal-to-detector distance 30 mm

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 > 2σ(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
N1	0.12987 (9)	0.09362 (13)	0.01219 (9)	0.0245 (2)
H1	0.0533 (13)	0.1035 (17)	−0.0336 (13)	0.029*
H2	0.1610 (12)	0.1948 (19)	0.0312 (13)	0.029*
N2	0.12725 (8)	−0.01011 (11)	0.11434 (8)	0.0206 (2)
C1	0.20987 (9)	−0.01413 (13)	0.21226 (10)	0.0192 (2)
C2	0.32112 (9)	0.09921 (13)	0.23046 (10)	0.0218 (3)
C3	0.28322 (11)	0.27995 (14)	0.24534 (11)	0.0276 (3)
H3A	0.3505	0.3512	0.2504	0.041*
H3B	0.2516	0.2903	0.3203	0.041*
H3C	0.2239	0.3107	0.1745	0.041*
C4	0.41908 (11)	0.06408 (16)	0.34566 (11)	0.0306 (3)
H4A	0.4808	0.1447	0.3500	0.046*
H4B	0.4510	−0.0442	0.3384	0.046*
H4C	0.3864	0.0699	0.4202	0.046*
C5	0.38405 (10)	0.07964 (15)	0.11793 (11)	0.0282 (3)
H5A	0.4509	0.1525	0.1282	0.042*
H5B	0.3300	0.1067	0.0420	0.042*
H5C	0.4103	−0.0324	0.1138	0.042*
C6	0.18503 (9)	−0.14007 (14)	0.31124 (10)	0.0222 (3)
C7	0.28249 (11)	−0.27168 (15)	0.34220 (13)	0.0333 (3)
H7A	0.3503	−0.2246	0.3959	0.050*
H7B	0.3043	−0.3094	0.2663	0.050*
H7C	0.2537	−0.3631	0.3838	0.050*
C8	0.16816 (11)	−0.05157 (17)	0.43156 (11)	0.0321 (3)
H8A	0.1509	−0.1315	0.4906	0.048*
H8B	0.1038	0.0252	0.4122	0.048*
H8C	0.2392	0.0068	0.4670	0.048*
C9	0.06898 (10)	−0.23344 (15)	0.26280 (11)	0.0290 (3)
H9A	0.0751	−0.2920	0.1877	0.044*
H9B	0.0048	−0.1561	0.2453	0.044*
H9C	0.0547	−0.3105	0.3252	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0230 (5)	0.0280 (5)	0.0210 (5)	−0.0030 (4)	0.0009 (4)	0.0050 (4)
N2	0.0206 (5)	0.0218 (5)	0.0193 (5)	0.0009 (4)	0.0038 (4)	0.0014 (3)
C1	0.0184 (5)	0.0185 (5)	0.0206 (5)	0.0013 (4)	0.0031 (4)	−0.0008 (4)
C2	0.0201 (5)	0.0225 (6)	0.0221 (5)	−0.0017 (4)	0.0023 (4)	0.0002 (4)
C3	0.0291 (6)	0.0233 (6)	0.0290 (6)	−0.0031 (5)	0.0028 (5)	−0.0023 (5)
C4	0.0241 (6)	0.0339 (7)	0.0303 (6)	−0.0044 (5)	−0.0035 (5)	0.0023 (5)
C5	0.0207 (6)	0.0340 (6)	0.0303 (6)	−0.0037 (5)	0.0058 (5)	−0.0022 (5)
C6	0.0219 (5)	0.0219 (6)	0.0225 (6)	0.0007 (4)	0.0036 (4)	0.0030 (4)
C7	0.0304 (6)	0.0261 (6)	0.0435 (7)	0.0047 (5)	0.0074 (5)	0.0095 (5)
C8	0.0351 (7)	0.0381 (7)	0.0240 (6)	−0.0018 (5)	0.0083 (5)	0.0006 (5)
C9	0.0281 (6)	0.0306 (6)	0.0280 (6)	−0.0062 (5)	0.0047 (5)	0.0061 (5)

Geometric parameters (Å, º)

N1—N2	1.3992 (13)	C5—H5A	0.9600
N1—H1	0.930 (15)	C5—H5B	0.9600
N1—H2	0.903 (16)	C5—H5C	0.9600
C1—N2	1.2864 (14)	C6—C7	1.5382 (15)
C1—C2	1.5585 (14)	C6—C9	1.5389 (15)
C1—C6	1.5504 (15)	C6—C8	1.5387 (16)
C2—C3	1.5448 (16)	C7—H7A	0.9600
C2—C4	1.5444 (15)	C7—H7B	0.9600
C2—C5	1.5482 (15)	C7—H7C	0.9600
C3—H3A	0.9600	C8—H8A	0.9600
C3—H3B	0.9600	C8—H8B	0.9600
C3—H3C	0.9600	C8—H8C	0.9600
C4—H4A	0.9600	C9—H9A	0.9600
C4—H4B	0.9600	C9—H9B	0.9600
C4—H4C	0.9600	C9—H9C	0.9600
N2—N1—H1	108.4 (8)	C2—C5—H5C	109.5
N2—N1—H2	115.5 (9)	H5A—C5—H5C	109.5
H1—N1—H2	109.8 (12)	H5B—C5—H5C	109.5
N1—N2—C1	123.28 (9)	C7—C6—C9	106.56 (10)
N2—C1—C2	123.39 (9)	C7—C6—C8	110.05 (10)
N2—C1—C6	112.76 (9)	C9—C6—C8	106.06 (9)
C2—C1—C6	123.83 (9)	C7—C6—C1	112.53 (9)
C3—C2—C4	105.46 (9)	C9—C6—C1	110.46 (9)
C3—C2—C5	111.43 (9)	C8—C6—C1	110.90 (9)
C4—C2—C5	104.10 (9)	C6—C7—H7A	109.5
C3—C2—C1	109.19 (9)	C6—C7—H7B	109.5
C4—C2—C1	116.74 (9)	H7A—C7—H7B	109.5
C5—C2—C1	109.80 (9)	C6—C7—H7C	109.5
C2—C3—H3A	109.5	H7A—C7—H7C	109.5
C2—C3—H3B	109.5	H7B—C7—H7C	109.5
H3A—C3—H3B	109.5	C6—C8—H8A	109.5
C2—C3—H3C	109.5	C6—C8—H8B	109.5
H3A—C3—H3C	109.5	H8A—C8—H8B	109.5
H3B—C3—H3C	109.5	C6—C8—H8C	109.5
C2—C4—H4A	109.5	H8A—C8—H8C	109.5
C2—C4—H4B	109.5	H8B—C8—H8C	109.5
H4A—C4—H4B	109.5	C6—C9—H9A	109.5
C2—C4—H4C	109.5	C6—C9—H9B	109.5
H4A—C4—H4C	109.5	H9A—C9—H9B	109.5
H4B—C4—H4C	109.5	C6—C9—H9C	109.5
C2—C5—H5A	109.5	H9A—C9—H9C	109.5
C2—C5—H5B	109.5	H9B—C9—H9C	109.5
H5A—C5—H5B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.930 (15)	2.230 (15)	3.0937 (13)	154.1 (12)

Symmetry code: (i) −x, −y, −z.

(II) di-tert-butyl ketone triphenylphosphoranylidenehydrazone

Crystal data

C27H33N2P	F(000) = 1792
Mr = 416.52	Dx = 1.160 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 122758 reflections
a = 29.1768 (16) Å	θ = 2.9–25.7°
b = 11.6848 (7) Å	µ = 0.13 mm^−1
c = 14.3768 (6) Å	T = 100 K
β = 103.243 (3)°	Platelet, colourless
V = 4771.1 (4) Å^3	0.17 × 0.15 × 0.10 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	6960 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.7°, θmin = 2.9°
two ϕ and two ω scans with 2° steps	h = −35→34
122758 measured reflections	k = −14→0
9059 independent reflections	l = 0→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 1.2906P] where P = (Fo^2 + 2Fc^2)/3
9059 reflections	(Δ/σ)max = 0.001
553 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. crystal-to-detector distance 30 mm

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 > 2σ(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
P1A	0.126578 (16)	0.87567 (4)	0.35509 (3)	0.02327 (12)
N1A	0.14460 (5)	0.98479 (14)	0.42084 (11)	0.0266 (4)
N2A	0.11641 (5)	0.99813 (14)	0.48864 (10)	0.0263 (3)
C1A	0.12476 (6)	1.08194 (17)	0.54874 (12)	0.0259 (4)
C2A	0.16387 (7)	1.17240 (17)	0.55023 (13)	0.0287 (4)
C3A	0.15162 (8)	1.23777 (18)	0.45438 (14)	0.0365 (5)
H3A	0.1462	1.1841	0.4025	0.055*
H3B	0.1773	1.2873	0.4499	0.055*
H3C	0.1237	1.2826	0.4512	0.055*
C4A	0.21186 (7)	1.11266 (19)	0.56231 (16)	0.0363 (5)
H4A	0.2118	1.0664	0.5071	0.055*
H4B	0.2175	1.0651	0.6182	0.055*
H4C	0.2363	1.1693	0.5691	0.055*
C5A	0.17153 (8)	1.26305 (18)	0.63071 (14)	0.0353 (5)
H5A	0.1928	1.3207	0.6185	0.053*
H5B	0.1846	1.2269	0.6909	0.053*
H5C	0.1419	1.2977	0.6326	0.053*
C6A	0.09036 (7)	1.08489 (18)	0.61627 (13)	0.0304 (4)
C7A	0.05684 (8)	1.1888 (2)	0.59358 (15)	0.0399 (5)
H7A	0.0749	1.2582	0.6036	0.060*
H7B	0.0352	1.1878	0.6349	0.060*
H7C	0.0396	1.1849	0.5282	0.060*
C8A	0.05893 (7)	0.97765 (19)	0.60192 (14)	0.0349 (5)
H8A	0.0369	0.9823	0.6422	0.052*
H8B	0.0782	0.9107	0.6183	0.052*
H8C	0.0421	0.9730	0.5363	0.052*
C9A	0.11642 (8)	1.0856 (2)	0.72279 (14)	0.0387 (5)
H9A	0.1271	1.1618	0.7412	0.058*
H9B	0.1430	1.0349	0.7322	0.058*
H9C	0.0954	1.0607	0.7612	0.058*
C10A	0.16748 (6)	0.86014 (17)	0.27903 (12)	0.0244 (4)
C11A	0.19999 (6)	0.94665 (18)	0.27593 (13)	0.0270 (4)
H11A	0.2008	1.0118	0.3135	0.032*
C12A	0.23112 (7)	0.93504 (19)	0.21645 (13)	0.0313 (4)
H12A	0.2528	0.9927	0.2142	0.038*
C13A	0.23009 (7)	0.83822 (19)	0.16058 (13)	0.0326 (5)
H13A	0.2514	0.8308	0.1217	0.039*
C14A	0.19749 (7)	0.75200 (18)	0.16222 (13)	0.0309 (4)
H14A	0.1968	0.6871	0.1246	0.037*
C15A	0.16587 (7)	0.76371 (18)	0.22069 (13)	0.0285 (4)
H15A	0.1435	0.7071	0.2210	0.034*
C16A	0.12308 (6)	0.74199 (17)	0.41682 (12)	0.0250 (4)
C17A	0.15670 (7)	0.65539 (17)	0.42471 (13)	0.0282 (4)
H17A	0.1812	0.6626	0.3937	0.034*
C18A	0.15360 (7)	0.55865 (18)	0.47878 (14)	0.0326 (5)
H18A	0.1758	0.5006	0.4830	0.039*
C19A	0.11766 (7)	0.54793 (18)	0.52643 (14)	0.0334 (5)
H19A	0.1158	0.4830	0.5628	0.040*
C20A	0.08434 (7)	0.63420 (18)	0.51988 (13)	0.0323 (5)
H20A	0.0604	0.6275	0.5526	0.039*
C21A	0.08671 (7)	0.73002 (17)	0.46483 (13)	0.0280 (4)
H21A	0.0640	0.7869	0.4597	0.034*
C22A	0.06880 (6)	0.88968 (17)	0.27444 (12)	0.0252 (4)
C23A	0.05362 (7)	0.99840 (18)	0.24230 (13)	0.0298 (4)
H23A	0.0720	1.0619	0.2651	0.036*
C24A	0.01105 (7)	1.01247 (19)	0.17608 (14)	0.0349 (5)
H24A	0.0012	1.0853	0.1541	0.042*
C25A	−0.01659 (7)	0.9182 (2)	0.14286 (14)	0.0358 (5)
H25A	−0.0452	0.9281	0.0990	0.043*
C26A	−0.00201 (7)	0.8095 (2)	0.17439 (13)	0.0328 (5)
H26A	−0.0207	0.7464	0.1518	0.039*
C27A	0.04077 (7)	0.79520 (18)	0.24010 (13)	0.0280 (4)
H27A	0.0507	0.7222	0.2612	0.034*
P1B	0.378096 (16)	0.63657 (4)	0.23986 (3)	0.02313 (12)
N1B	0.35412 (6)	0.52716 (14)	0.27612 (11)	0.0278 (4)
N2B	0.38056 (5)	0.49398 (14)	0.36776 (10)	0.0268 (4)
C1B	0.36555 (7)	0.41133 (17)	0.41229 (13)	0.0271 (4)
C2B	0.31963 (8)	0.34335 (18)	0.37059 (14)	0.0344 (5)
C3B	0.32498 (9)	0.2847 (2)	0.27700 (15)	0.0422 (5)
H3D	0.3503	0.2304	0.2912	0.063*
H3E	0.3317	0.3415	0.2337	0.063*
H3F	0.2962	0.2460	0.2480	0.063*
C4B	0.30603 (9)	0.2474 (2)	0.43339 (17)	0.0494 (6)
H4D	0.2990	0.2804	0.4897	0.074*
H4E	0.3318	0.1947	0.4515	0.074*
H4F	0.2788	0.2074	0.3979	0.074*
C5B	0.27741 (7)	0.4265 (2)	0.35038 (16)	0.0416 (5)
H5D	0.2493	0.3855	0.3210	0.062*
H5E	0.2829	0.4860	0.3082	0.062*
H5F	0.2738	0.4597	0.4093	0.062*
C6B	0.39857 (7)	0.38686 (18)	0.51135 (13)	0.0319 (5)
C7B	0.42194 (10)	0.2684 (2)	0.51370 (18)	0.0564 (7)
H7D	0.4435	0.2576	0.5744	0.085*
H7E	0.4387	0.2638	0.4636	0.085*
H7F	0.3982	0.2100	0.5046	0.085*
C8B	0.37278 (8)	0.3972 (2)	0.59324 (14)	0.0421 (5)
H8D	0.3539	0.3302	0.5944	0.063*
H8E	0.3529	0.4637	0.5833	0.063*
H8F	0.3955	0.4041	0.6530	0.063*
C9B	0.43916 (7)	0.4743 (2)	0.53285 (14)	0.0385 (5)
H9D	0.4600	0.4562	0.5930	0.058*
H9E	0.4266	0.5497	0.5357	0.058*
H9F	0.4562	0.4714	0.4832	0.058*
C10B	0.33994 (6)	0.67597 (17)	0.12737 (12)	0.0244 (4)
C11B	0.29963 (6)	0.61255 (17)	0.08934 (13)	0.0272 (4)
H11B	0.2919	0.5497	0.1223	0.033*
C12B	0.27094 (7)	0.64374 (18)	0.00143 (13)	0.0295 (4)
H12B	0.2437	0.6022	−0.0238	0.035*
C13B	0.28284 (7)	0.73639 (17)	−0.04838 (13)	0.0277 (4)
H13B	0.2638	0.7562	−0.1073	0.033*
C14B	0.32301 (6)	0.79976 (17)	−0.01077 (13)	0.0265 (4)
H14B	0.3308	0.8623	−0.0441	0.032*
C15B	0.35146 (6)	0.76939 (17)	0.07655 (13)	0.0262 (4)
H15B	0.3785	0.8115	0.1016	0.031*
C16B	0.38592 (6)	0.76161 (16)	0.31634 (12)	0.0238 (4)
C17B	0.35309 (7)	0.85021 (17)	0.30093 (14)	0.0283 (4)
H17B	0.3285	0.8495	0.2468	0.034*
C18B	0.35692 (7)	0.93974 (18)	0.36592 (14)	0.0318 (4)
H18B	0.3348	0.9985	0.3555	0.038*
C19B	0.39361 (7)	0.94128 (18)	0.44607 (13)	0.0316 (4)
H19B	0.3961	1.0010	0.4897	0.038*
C20B	0.42681 (7)	0.85385 (17)	0.46162 (13)	0.0302 (4)
H20B	0.4517	0.8558	0.5152	0.036*
C21B	0.42292 (6)	0.76391 (17)	0.39751 (12)	0.0260 (4)
H21B	0.4450	0.7050	0.4085	0.031*
C22B	0.43638 (6)	0.61407 (17)	0.21741 (12)	0.0262 (4)
C23B	0.46780 (7)	0.70383 (19)	0.21720 (13)	0.0294 (4)
H23B	0.4595	0.7778	0.2308	0.035*
C24B	0.51144 (7)	0.6836 (2)	0.19675 (13)	0.0362 (5)
H24B	0.5326	0.7435	0.1980	0.043*
C25B	0.52328 (7)	0.5733 (2)	0.17451 (14)	0.0400 (5)
H25B	0.5524	0.5594	0.1607	0.048*
C26B	0.49195 (7)	0.4842 (2)	0.17275 (14)	0.0374 (5)
H26B	0.4998	0.4109	0.1565	0.045*
C27B	0.44870 (7)	0.50368 (18)	0.19527 (13)	0.0319 (4)
H27B	0.4280	0.4432	0.1956	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.0242 (2)	0.0232 (3)	0.0227 (2)	0.00044 (19)	0.00580 (19)	−0.00069 (19)
N1A	0.0292 (8)	0.0260 (9)	0.0258 (8)	−0.0013 (7)	0.0089 (7)	−0.0024 (6)
N2A	0.0279 (8)	0.0279 (9)	0.0238 (8)	0.0031 (7)	0.0073 (7)	−0.0006 (7)
C1A	0.0274 (10)	0.0262 (11)	0.0228 (9)	0.0055 (8)	0.0031 (8)	−0.0005 (7)
C2A	0.0310 (10)	0.0244 (11)	0.0302 (10)	0.0020 (8)	0.0059 (8)	−0.0020 (8)
C3A	0.0488 (13)	0.0254 (12)	0.0354 (11)	−0.0026 (10)	0.0102 (10)	0.0009 (9)
C4A	0.0304 (11)	0.0324 (12)	0.0447 (12)	−0.0018 (9)	0.0055 (9)	−0.0077 (9)
C5A	0.0405 (12)	0.0279 (12)	0.0350 (11)	0.0007 (9)	0.0035 (9)	−0.0060 (9)
C6A	0.0317 (10)	0.0335 (12)	0.0270 (10)	0.0046 (9)	0.0088 (8)	−0.0012 (8)
C7A	0.0397 (12)	0.0421 (14)	0.0411 (12)	0.0106 (10)	0.0160 (10)	0.0003 (10)
C8A	0.0342 (11)	0.0401 (13)	0.0332 (10)	0.0014 (9)	0.0137 (9)	0.0023 (9)
C9A	0.0433 (12)	0.0472 (14)	0.0263 (10)	0.0028 (11)	0.0095 (9)	−0.0005 (9)
C10A	0.0231 (9)	0.0267 (11)	0.0223 (9)	0.0040 (8)	0.0029 (7)	0.0010 (7)
C11A	0.0273 (10)	0.0297 (11)	0.0236 (9)	0.0018 (8)	0.0049 (8)	0.0004 (8)
C12A	0.0259 (10)	0.0401 (13)	0.0279 (10)	0.0005 (9)	0.0063 (8)	0.0043 (9)
C13A	0.0276 (10)	0.0442 (13)	0.0270 (10)	0.0080 (9)	0.0080 (8)	0.0024 (9)
C14A	0.0315 (10)	0.0348 (12)	0.0257 (9)	0.0075 (9)	0.0054 (8)	−0.0029 (8)
C15A	0.0278 (10)	0.0289 (11)	0.0278 (9)	0.0017 (8)	0.0043 (8)	−0.0011 (8)
C16A	0.0279 (10)	0.0248 (10)	0.0207 (8)	−0.0020 (8)	0.0022 (7)	−0.0018 (7)
C17A	0.0287 (10)	0.0268 (11)	0.0277 (9)	−0.0010 (8)	0.0035 (8)	−0.0029 (8)
C18A	0.0372 (11)	0.0241 (11)	0.0329 (10)	0.0020 (9)	0.0003 (9)	−0.0002 (8)
C19A	0.0422 (12)	0.0280 (12)	0.0277 (10)	−0.0057 (9)	0.0030 (9)	0.0026 (8)
C20A	0.0367 (11)	0.0331 (12)	0.0264 (10)	−0.0075 (9)	0.0062 (8)	−0.0018 (8)
C21A	0.0288 (10)	0.0302 (11)	0.0243 (9)	−0.0002 (8)	0.0047 (8)	−0.0016 (8)
C22A	0.0263 (9)	0.0287 (11)	0.0221 (9)	0.0025 (8)	0.0088 (7)	−0.0001 (7)
C23A	0.0311 (10)	0.0295 (11)	0.0302 (10)	0.0042 (9)	0.0096 (8)	−0.0013 (8)
C24A	0.0355 (11)	0.0369 (13)	0.0332 (10)	0.0132 (10)	0.0097 (9)	0.0047 (9)
C25A	0.0272 (10)	0.0501 (15)	0.0295 (10)	0.0061 (10)	0.0051 (8)	0.0026 (9)
C26A	0.0280 (10)	0.0412 (13)	0.0288 (10)	−0.0055 (9)	0.0058 (8)	−0.0004 (9)
C27A	0.0308 (10)	0.0291 (11)	0.0248 (9)	−0.0004 (8)	0.0077 (8)	0.0018 (8)
P1B	0.0238 (2)	0.0233 (3)	0.0222 (2)	−0.0006 (2)	0.00493 (18)	−0.00040 (18)
N1B	0.0315 (9)	0.0267 (9)	0.0238 (8)	−0.0012 (7)	0.0035 (7)	0.0018 (6)
N2B	0.0309 (8)	0.0265 (9)	0.0231 (8)	0.0027 (7)	0.0066 (7)	0.0010 (6)
C1B	0.0324 (10)	0.0236 (10)	0.0268 (9)	0.0010 (8)	0.0098 (8)	−0.0002 (8)
C2B	0.0414 (12)	0.0294 (12)	0.0326 (10)	−0.0079 (9)	0.0090 (9)	0.0006 (8)
C3B	0.0605 (15)	0.0312 (13)	0.0356 (11)	−0.0096 (11)	0.0122 (10)	−0.0055 (9)
C4B	0.0634 (16)	0.0429 (15)	0.0435 (13)	−0.0207 (12)	0.0152 (12)	0.0044 (11)
C5B	0.0354 (12)	0.0457 (14)	0.0426 (12)	−0.0116 (10)	0.0069 (10)	−0.0035 (10)
C6B	0.0400 (11)	0.0297 (12)	0.0259 (10)	0.0045 (9)	0.0075 (9)	0.0040 (8)
C7B	0.0692 (17)	0.0388 (15)	0.0550 (15)	0.0204 (13)	0.0013 (13)	0.0039 (12)
C8B	0.0488 (13)	0.0509 (15)	0.0266 (10)	−0.0051 (11)	0.0088 (10)	0.0053 (9)
C9B	0.0356 (11)	0.0469 (14)	0.0302 (10)	−0.0007 (10)	0.0017 (9)	0.0056 (9)
C10B	0.0248 (9)	0.0262 (11)	0.0229 (9)	0.0011 (8)	0.0069 (7)	−0.0012 (7)
C11B	0.0289 (10)	0.0259 (11)	0.0272 (9)	−0.0028 (8)	0.0070 (8)	0.0004 (8)
C12B	0.0271 (10)	0.0338 (12)	0.0265 (9)	−0.0025 (8)	0.0041 (8)	−0.0025 (8)
C13B	0.0295 (10)	0.0303 (11)	0.0232 (9)	0.0042 (8)	0.0055 (8)	0.0003 (8)
C14B	0.0287 (10)	0.0257 (11)	0.0269 (9)	0.0024 (8)	0.0103 (8)	0.0023 (8)
C15B	0.0230 (9)	0.0262 (11)	0.0296 (10)	−0.0020 (8)	0.0063 (8)	−0.0002 (8)
C16B	0.0257 (9)	0.0247 (10)	0.0227 (9)	−0.0027 (8)	0.0089 (7)	−0.0010 (7)
C17B	0.0277 (10)	0.0286 (11)	0.0285 (9)	−0.0010 (8)	0.0061 (8)	−0.0011 (8)
C18B	0.0361 (11)	0.0261 (11)	0.0350 (10)	0.0041 (9)	0.0121 (9)	0.0007 (8)
C19B	0.0437 (12)	0.0250 (11)	0.0286 (10)	−0.0066 (9)	0.0137 (9)	−0.0041 (8)
C20B	0.0353 (11)	0.0325 (12)	0.0228 (9)	−0.0080 (9)	0.0066 (8)	−0.0003 (8)
C21B	0.0273 (9)	0.0280 (11)	0.0242 (9)	−0.0016 (8)	0.0086 (8)	0.0016 (8)
C22B	0.0268 (10)	0.0311 (11)	0.0197 (8)	0.0037 (8)	0.0032 (7)	−0.0010 (8)
C23B	0.0280 (10)	0.0351 (12)	0.0252 (9)	−0.0006 (9)	0.0060 (8)	−0.0038 (8)
C24B	0.0252 (10)	0.0545 (15)	0.0287 (10)	−0.0025 (10)	0.0056 (8)	−0.0066 (9)
C25B	0.0292 (11)	0.0629 (16)	0.0270 (10)	0.0139 (11)	0.0048 (8)	−0.0007 (10)
C26B	0.0404 (12)	0.0413 (14)	0.0300 (10)	0.0179 (10)	0.0072 (9)	0.0026 (9)
C27B	0.0373 (11)	0.0320 (12)	0.0255 (9)	0.0072 (9)	0.0058 (8)	0.0031 (8)

Geometric parameters (Å, º)

P1A—N1A	1.6025 (16)	P1B—N1B	1.6008 (16)
P1A—C10A	1.8030 (18)	P1B—C10B	1.8006 (18)
P1A—C16A	1.811 (2)	P1B—C16B	1.8114 (19)
P1A—C22A	1.8214 (19)	P1B—C22B	1.8212 (19)
N1A—N2A	1.421 (2)	N1B—N2B	1.420 (2)
C1A—N2A	1.292 (2)	C1B—N2B	1.289 (2)
C1A—C2A	1.552 (3)	C1B—C2B	1.555 (3)
C1A—C6A	1.548 (3)	C1B—C6B	1.552 (3)
C2A—C4A	1.538 (3)	C2B—C5B	1.543 (3)
C2A—C3A	1.544 (3)	C2B—C4B	1.548 (3)
C2A—C5A	1.547 (3)	C2B—C3B	1.549 (3)
C3A—H3A	0.9600	C3B—H3D	0.9600
C3A—H3B	0.9600	C3B—H3E	0.9600
C3A—H3C	0.9600	C3B—H3F	0.9600
C4A—H4A	0.9600	C4B—H4D	0.9600
C4A—H4B	0.9600	C4B—H4E	0.9600
C4A—H4C	0.9600	C4B—H4F	0.9600
C5A—H5A	0.9600	C5B—H5D	0.9600
C5A—H5B	0.9600	C5B—H5E	0.9600
C5A—H5C	0.9600	C5B—H5F	0.9600
C6A—C8A	1.538 (3)	C6B—C7B	1.540 (3)
C6A—C9A	1.546 (3)	C6B—C8B	1.540 (3)
C6A—C7A	1.546 (3)	C6B—C9B	1.541 (3)
C7A—H7A	0.9600	C7B—H7D	0.9600
C7A—H7B	0.9600	C7B—H7E	0.9600
C7A—H7C	0.9600	C7B—H7F	0.9600
C8A—H8A	0.9600	C8B—H8D	0.9600
C8A—H8B	0.9600	C8B—H8E	0.9600
C8A—H8C	0.9600	C8B—H8F	0.9600
C9A—H9A	0.9600	C9B—H9D	0.9600
C9A—H9B	0.9600	C9B—H9E	0.9600
C9A—H9C	0.9600	C9B—H9F	0.9600
C10A—C11A	1.394 (3)	C10B—C11B	1.392 (3)
C10A—C15A	1.399 (3)	C10B—C15B	1.397 (3)
C11A—C12A	1.389 (3)	C11B—C12B	1.395 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.384 (3)	C12B—C13B	1.385 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.389 (3)	C13B—C14B	1.387 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.390 (3)	C14B—C15B	1.383 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.396 (3)	C16B—C17B	1.393 (3)
C16A—C21A	1.399 (3)	C16B—C21B	1.397 (3)
C17A—C18A	1.387 (3)	C17B—C18B	1.390 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.383 (3)	C18B—C19B	1.382 (3)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.389 (3)	C19B—C20B	1.390 (3)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.382 (3)	C20B—C21B	1.385 (3)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.389 (3)	C22B—C23B	1.393 (3)
C22A—C27A	1.395 (3)	C22B—C27B	1.395 (3)
C23A—C24A	1.391 (3)	C23B—C24B	1.391 (3)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.384 (3)	C24B—C25B	1.390 (3)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.382 (3)	C25B—C26B	1.382 (3)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—C27A	1.392 (3)	C26B—C27B	1.391 (3)
C26A—H26A	0.9300	C26B—H26B	0.9300
C27A—H27A	0.9300	C27B—H27B	0.9300
P1A—N1A—N2A	109.19 (12)	N1B—P1B—C10B	105.68 (9)
N1A—N2A—C1A	119.47 (16)	N1B—P1B—C16B	116.75 (8)
N2A—C1A—C2A	123.44 (17)	C10B—P1B—C16B	107.76 (9)
N2A—C1A—C6A	112.72 (17)	N1B—P1B—C22B	115.97 (9)
C2A—C1A—C6A	123.80 (16)	C10B—P1B—C22B	106.74 (8)
N1A—P1A—C10A	105.33 (8)	C16B—P1B—C22B	103.36 (9)
N1A—P1A—C16A	116.42 (8)	P1B—N1B—N2B	109.58 (12)
C10A—P1A—C16A	109.26 (9)	N1B—N2B—C1B	119.41 (16)
N1A—P1A—C22A	115.77 (9)	N2B—C1B—C2B	123.49 (17)
C10A—P1A—C22A	105.52 (8)	N2B—C1B—C6B	112.55 (17)
C16A—P1A—C22A	103.98 (9)	C2B—C1B—C6B	123.95 (16)
C4A—C2A—C3A	110.10 (16)	C5B—C2B—C4B	105.42 (18)
C4A—C2A—C5A	104.74 (16)	C5B—C2B—C3B	110.48 (18)
C3A—C2A—C5A	107.04 (17)	C4B—C2B—C3B	106.06 (18)
C4A—C2A—C1A	109.86 (16)	C5B—C2B—C1B	109.33 (17)
C3A—C2A—C1A	107.79 (16)	C4B—C2B—C1B	117.31 (17)
C5A—C2A—C1A	117.17 (16)	C3B—C2B—C1B	108.14 (16)
C2A—C3A—H3A	109.5	C2B—C3B—H3D	109.5
C2A—C3A—H3B	109.5	C2B—C3B—H3E	109.5
H3A—C3A—H3B	109.5	H3D—C3B—H3E	109.5
C2A—C3A—H3C	109.5	C2B—C3B—H3F	109.5
H3A—C3A—H3C	109.5	H3D—C3B—H3F	109.5
H3B—C3A—H3C	109.5	H3E—C3B—H3F	109.5
C2A—C4A—H4A	109.5	C2B—C4B—H4D	109.5
C2A—C4A—H4B	109.5	C2B—C4B—H4E	109.5
H4A—C4A—H4B	109.5	H4D—C4B—H4E	109.5
C2A—C4A—H4C	109.5	C2B—C4B—H4F	109.5
H4A—C4A—H4C	109.5	H4D—C4B—H4F	109.5
H4B—C4A—H4C	109.5	H4E—C4B—H4F	109.5
C2A—C5A—H5A	109.5	C2B—C5B—H5D	109.5
C2A—C5A—H5B	109.5	C2B—C5B—H5E	109.5
H5A—C5A—H5B	109.5	H5D—C5B—H5E	109.5
C2A—C5A—H5C	109.5	C2B—C5B—H5F	109.5
H5A—C5A—H5C	109.5	H5D—C5B—H5F	109.5
H5B—C5A—H5C	109.5	H5E—C5B—H5F	109.5
C8A—C6A—C9A	106.27 (17)	C7B—C6B—C8B	110.18 (19)
C8A—C6A—C7A	106.41 (17)	C7B—C6B—C9B	105.97 (19)
C9A—C6A—C7A	110.38 (17)	C8B—C6B—C9B	106.40 (17)
C8A—C6A—C1A	110.48 (16)	C7B—C6B—C1B	111.37 (17)
C9A—C6A—C1A	112.26 (16)	C8B—C6B—C1B	112.19 (17)
C7A—C6A—C1A	110.78 (16)	C9B—C6B—C1B	110.42 (16)
C6A—C7A—H7A	109.5	C6B—C7B—H7D	109.5
C6A—C7A—H7B	109.5	C6B—C7B—H7E	109.5
H7A—C7A—H7B	109.5	H7D—C7B—H7E	109.5
C6A—C7A—H7C	109.5	C6B—C7B—H7F	109.5
H7A—C7A—H7C	109.5	H7D—C7B—H7F	109.5
H7B—C7A—H7C	109.5	H7E—C7B—H7F	109.5
C6A—C8A—H8A	109.5	C6B—C8B—H8D	109.5
C6A—C8A—H8B	109.5	C6B—C8B—H8E	109.5
H8A—C8A—H8B	109.5	H8D—C8B—H8E	109.5
C6A—C8A—H8C	109.5	C6B—C8B—H8F	109.5
H8A—C8A—H8C	109.5	H8D—C8B—H8F	109.5
H8B—C8A—H8C	109.5	H8E—C8B—H8F	109.5
C6A—C9A—H9A	109.5	C6B—C9B—H9D	109.5
C6A—C9A—H9B	109.5	C6B—C9B—H9E	109.5
H9A—C9A—H9B	109.5	H9D—C9B—H9E	109.5
C6A—C9A—H9C	109.5	C6B—C9B—H9F	109.5
H9A—C9A—H9C	109.5	H9D—C9B—H9F	109.5
H9B—C9A—H9C	109.5	H9E—C9B—H9F	109.5
C11A—C10A—C15A	119.64 (17)	C11B—C10B—C15B	119.59 (17)
C11A—C10A—P1A	119.75 (15)	C11B—C10B—P1B	120.64 (14)
C15A—C10A—P1A	120.58 (15)	C15B—C10B—P1B	119.75 (14)
C12A—C11A—C10A	119.63 (19)	C10B—C11B—C12B	119.64 (18)
C12A—C11A—H11A	120.2	C10B—C11B—H11B	120.2
C10A—C11A—H11A	120.2	C12B—C11B—H11B	120.2
C13A—C12A—C11A	120.45 (19)	C13B—C12B—C11B	120.20 (18)
C13A—C12A—H12A	119.8	C13B—C12B—H12B	119.9
C11A—C12A—H12A	119.8	C11B—C12B—H12B	119.9
C12A—C13A—C14A	120.45 (18)	C12B—C13B—C14B	120.33 (17)
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.8
C14A—C13A—H13A	119.8	C14B—C13B—H13B	119.8
C15A—C14A—C13A	119.39 (19)	C15B—C14B—C13B	119.65 (18)
C15A—C14A—H14A	120.3	C15B—C14B—H14B	120.2
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.2
C14A—C15A—C10A	120.40 (19)	C14B—C15B—C10B	120.59 (18)
C14A—C15A—H15A	119.8	C14B—C15B—H15B	119.7
C10A—C15A—H15A	119.8	C10B—C15B—H15B	119.7
C17A—C16A—C21A	119.07 (18)	C17B—C16B—C21B	119.36 (17)
C17A—C16A—P1A	123.20 (14)	C17B—C16B—P1B	121.09 (14)
C21A—C16A—P1A	117.53 (15)	C21B—C16B—P1B	119.24 (15)
C18A—C17A—C16A	120.11 (18)	C18B—C17B—C16B	120.39 (18)
C18A—C17A—H17A	119.9	C18B—C17B—H17B	119.8
C16A—C17A—H17A	119.9	C16B—C17B—H17B	119.8
C19A—C18A—C17A	120.38 (19)	C19B—C18B—C17B	119.87 (19)
C19A—C18A—H18A	119.8	C19B—C18B—H18B	120.1
C17A—C18A—H18A	119.8	C17B—C18B—H18B	120.1
C18A—C19A—C20A	119.93 (19)	C18B—C19B—C20B	120.18 (18)
C18A—C19A—H19A	120.0	C18B—C19B—H19B	119.9
C20A—C19A—H19A	120.0	C20B—C19B—H19B	119.9
C21A—C20A—C19A	120.06 (19)	C21B—C20B—C19B	120.17 (18)
C21A—C20A—H20A	120.0	C21B—C20B—H20B	119.9
C19A—C20A—H20A	120.0	C19B—C20B—H20B	119.9
C20A—C21A—C16A	120.44 (19)	C20B—C21B—C16B	120.02 (18)
C20A—C21A—H21A	119.8	C20B—C21B—H21B	120.0
C16A—C21A—H21A	119.8	C16B—C21B—H21B	120.0
C23A—C22A—C27A	119.31 (18)	C23B—C22B—C27B	119.43 (18)
C23A—C22A—P1A	118.16 (15)	C23B—C22B—P1B	122.23 (15)
C27A—C22A—P1A	122.43 (15)	C27B—C22B—P1B	118.27 (15)
C22A—C23A—C24A	120.2 (2)	C24B—C23B—C22B	120.5 (2)
C22A—C23A—H23A	119.9	C24B—C23B—H23B	119.8
C24A—C23A—H23A	119.9	C22B—C23B—H23B	119.8
C25A—C24A—C23A	120.0 (2)	C25B—C24B—C23B	119.6 (2)
C25A—C24A—H24A	120.0	C25B—C24B—H24B	120.2
C23A—C24A—H24A	120.0	C23B—C24B—H24B	120.2
C26A—C25A—C24A	120.45 (19)	C26B—C25B—C24B	120.31 (19)
C26A—C25A—H25A	119.8	C26B—C25B—H25B	119.8
C24A—C25A—H25A	119.8	C24B—C25B—H25B	119.8
C25A—C26A—C27A	119.6 (2)	C25B—C26B—C27B	120.2 (2)
C25A—C26A—H26A	120.2	C25B—C26B—H26B	119.9
C27A—C26A—H26A	120.2	C27B—C26B—H26B	119.9
C26A—C27A—C22A	120.44 (19)	C26B—C27B—C22B	119.9 (2)
C26A—C27A—H27A	119.8	C26B—C27B—H27B	120.0
C22A—C27A—H27A	119.8	C22B—C27B—H27B	120.0