Bis{[phthalocyaninato(2–)]arsenic(III)} octa­iodo­diarsenic(III)

Crystals of the novel title arsenic(III)–phthalocyanine complex, [As(C₃₂H₁₆N₈)]₂[As₂I₈] or [AsPc]₂[As₂I₈], where Pc is the phthalocyaninate(2−) macrocycle, have been obtained from the reaction of pure powdered arsenic with phthalonitrile under oxidizing conditions (iodine vapour) at 463 K. The crystals are formed by separate but inter­acting [AsPc]⁺ cations and centrosymmetric [As₂I₈]²⁻ anions. The As atom of the [AsPc]⁺ ion is bonded to the four isoindole N atoms of the Pc macrocycle and lies 0.762 (1) Å out of their plane. The anionic part of the complex consists of two [AsI₄]⁻ units joined together into a centrosymmetric [As₂I₈]²⁻ counter-ion. The arrangement of oppositely charged moieties, viz. [AsPc]⁺ and [As₂I₈]²⁻, in the crystal structure is determined mainly by their ionic attractions and by π–π inter­actions between the aromatic phthalocyaninate(2−) macrocycles.

S1. Comment

The present study is part of an investigation on the synthesis, characterization and stereochemistry of metallophthalocyaninate complexes obtained under oxidizing conditions under iodine vapour. In the partially oxidized iodine-doped metallophthalocyanines and metallodiphthalocyanines, the I atoms form linear chains of symmetrical I₃⁻ ions, which are usually disordered (Janczak, Kubiak & Jezierski, 1999; Janczak & Idemori, 2001a) or ordered in the crystal structure (Janczak, 2003); in metallophthalocyanines, the I atoms are directly linked to the central metal ion, yielding mono- or diiodometallophthalocyanines (Janczak & Kubiak, 1999a,b; Janczak & Idemori, 2001b). Alternatively, the I atoms can form a neutral I₂ molecule, which acts as a bridge for dimerization (Janczak, Kubiak & Hahn, 1999; Janczak, 2004) or for developing a polymeric supramolecular structure (Janczak, Razik & Kubiak, 1999; Janczak & Idemori, 2002a).

The metallophthalocyanines with group 15 metals are less well investigated. The title compound, (I), is an example of a phthalocyaninate (Pc) complex containing the same metal in both the cation and the anion, i.e. [AsPc]⁺ and [As₂I₈]²⁻. A search of the Cambridge Structural Database (Version 5.24; Allen, 2002) for phthalocyaninate structures containing the same metal in both parts of the complex gives only [(SbPc)₄(Sb₄I₁₆)] (Janczak & Idemori, 2002b), [(BiPc)₄(Bi₄I₁₆)] (Kubiak & Ejsmont, 1999), [(AsPc)₂(As₄I₁₄)] (Janczak & Kubiak, 2003) and [(SbPc)₂(Sb₄I₁₄)] (Perpétuo & Janczak, 2005), none of which contain the [M₂I₈]²⁻ ion. The present [AsPc]₂[As₂I₈] structure is therefore the first example of this type of phthalocyaninate system.

The crystal structure of (I) is built up of separate but interacting [AsPc]⁺ and [As₂I₈]²⁻ units (Fig. 1). The phthalocyaninate(2-) macrocycle of the [AsPc]⁺ moiety is saucer-shaped as a result of the interaction of the central As^III ion with the oppositely charged [As₂I₈]²⁻ counter-ion. The greatest deviations from the plane defined by the four isoindole N atoms of the phthalocyaninate macrocycle are observed for the outermost C atoms of the phenyl rings, ranging from 0.074 (1) to 0.346 (1) Å for the C2–C7 ring. The positively charged As^III atom of the [AsPc]⁺ cation, which is coordinated by the four isoindole N atoms, is significantly displaced from the N₄-isoindole plane [0.762 (1) Å] towards atoms I2, I3 and I4 of the [As₂I₈]²⁻ anion. The As2···I2ⁱ [symmetry code: (i) −x + 1/2, −y + 3/2, −z + 1], As2···I4 and As2···I3 distances of 3.5376 (9), 3.5655 (8) and 3.7941 (9) Å, respectively, are shorter than the sum of the van der Waals radii of As and I atoms (Shannon, 1976). The displacement of the As^III atom from the N₄-isoindole plane is comparable to that observed in phthalocyaninato(2-)arsenic(III) triiodide [0.757 (2) Å; Janczak & Idemori, 2002c] and in bis[phthalocyaninato(2-)arsenic(III)] tetradecaiodotetraarsenic(III) [0.743 (3) Å; Janczak & Kubiak, 2003]. In the Sb^III–phthalocyanine (Kubiak & Razik, 1998), Sb^III–phthalocyanine triiodide (Kubiak, Janczak & Razik, 1999) and two Sb^III–phthalocyanine Sb^III–iodine complexes (Janczak & Idemori, 2002b; Perpétuo & Janczak, 2005), the displacement of the central Sb atom from the N₄-isoindole plane is ~0.25 Å greater than that observed in the As^III–phthalocyaninate(2-) complexes. This difference is quite reasonable, because of the difference between the ionic radii of As^III and Sb^III (Shannon, 1976). The ionic attraction between the [AsPc]⁺ and [As₂I₈]²⁻ ions is clearly manifested in the As—N coordination, leading to the molecular symmetry of the As—N₄ core being close to C_s rather than C_4v, which corresponds to the conformation in solution. The displacement of the As^III atom from the N₄-isoindole plane is significantly greater in the unique example of a partially oxidized I-doped As^III–phthalocyaninate metal-free phthalocyanine complex [0.975 (2) Å; Janczak, Kubiak & Jezierski, 1999], as a result of the location of the As atom between the two phthalocyaninate rings.

The anionic part of (I) consists of two AsI₄⁻ moieties joined together by two bridging I atoms to form the centrosymmetic [As₂I₈]²⁻ anion. The As—I bond lengths fall into two groups, namely shorter As—I bonds, which join the terminal I atoms, and longer As—I bonds with the I-bridging atoms. Thus the [As₂I₈]²⁻ counter-ion can be viewed as two distorted square-pyramidal AsI₅ polyhedra linked together by one edge. The distortion of the AsI₅ units from ideal square-pyramidal geometry is probably due to the lone electron pair on the As^III atoms predicted by the valence-shell electron-pair repulsion model (Gillespie, 1963, 1992), as well as to the interaction with the oppositely charged [AsPc]⁺ counter-ion. Looking in more detail at the As—I bond lengths in the [As₂I₈]²⁻ ion, it is clear that the I atoms are linked to As with different strengths; atom I3 is linked more strongly than atom I1, and atom I1 more strongly than atom I4 (Table 1). These differences correlate with the strength of the interactions between the I atoms in the [As₂I₈]²⁻ anion and the oppositely charged As^III atom of the [AsPc]⁺ moiety. The strongest interaction between the [AsPc]⁺ and the [As₂I₈]²⁻ ions takes place between the As atom of the [AsPc]⁺ ion and the bridging I atom of the [As₂I₈]²⁻ ion [As2···I2ⁱ = 3.5376 (9) Å].

The ionic attraction between the [AsPc]⁺ and [As₂I₈]²⁻ ions seems to be significant in the crystal structure (Fig. 2). The basic packing unit includes two [AsPc]⁺ complexes related by an inversion centre and one centrosymmetric [As₂I₈]²⁻ counter-ion. The positively charged [AsPc]⁺ moieties are attached to the [As₂I₈]²⁻ anion on both sides, forming centrosymmetric [(AsPc)(As₂I₈)(AsPc)] aggregates with a distance of ~10.11 (1) Å between the N₄-isoindole planes. These aggregates form stacks that are propagated along the [101] direction. The distance of ~3.41 (1) Å between the N₄-isoindole planes of two neighbouring [AsPc]⁺ units within the stack indicates strong π–π interaction between Pc macrocycles (Pauling, 1960). The π–π intermolecular interaction is a common feature of phthalocyanine chemistry, and it leads phthalocyanine and its metal complexes to form supramolecular aggregates (Nevin et al., 1987; Terekhov et al., 1996; Isago et al., 1997, 1998).

Although the crystal of [(AsPc)₂(As₂I₈)] is built up from oppositely charged [AsPc]⁺ and As₂I₈]²⁻ ions, the compound does not possess the characteristic properties of ionic crystals. The solubility of this compound in most polar solvents, such as water, methanol, ethanol and acetone, is insignificant, and it is slightly soluble in pyridine, dimethyl sulfoxide, tetrahydrofuran, chloronaphthalene and other aromatic solvents. This is in agreement with the crystal structure, in which both hydrophilic parts of the complex are surrounded by the hydrophobic phenyl rings of the Pc macrocycle.

The electrical conductivity of (I) measured from a single-crystal along the stacking direction of the {[AsPc]⁺···[As₂I₈]²⁻···[AsPc]⁺} aggregates (along the [101] direction) as well as along the b axis (perpendicular to the stacks), exhibits non-metallic character (dσ/dT > 0). At room temperature the conductivity is ~4.4–5.1 × 10⁻⁶ Ω⁻¹ cm⁻¹ along [101] and ~5.8–6.5 × 10⁻⁷ Ω⁻¹ cm⁻¹ along the b axis.

S2. Experimental

The crystals of the title compound were obtained by the direct reaction of pure powdered arsenic with phthalonitrile (Kubiak & Janczak, 1993) under a stream of iodine vapour at 463 K. [Quantities of reagents?]

S3. Refinement

The greatest positive and negative residual electron densities are located at the positions (0.1871, 0.2648, 0.3078) and (0.1269, 0.6243, 0.3007), respectively.

Computing details

Data collection: KM-4 CCD Software (Kuma 2001); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990b); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the molecular structure of the (a) [AsPc]^+ and (b) [As2I8]^2− units with the labelling of the atoms. Displacement ellipsoids are shown at the 50% probability level and H atoms as spheres of arbitrary radii. [Symmetry code: (i) −x 1/2, −y + 3/2, −z + 1.]
	Fig. 2. The molecular stacking in the extended structure. The dashed lines represent the As···I interactions between the [AsPc]^+ and [As2I8]^2− units. The distances d1 and d2 are 3.41 and 10.11 Å.

Bis{[phthalocyaninato(2-)]arsenic(III)} octaiododiarsenic(III)

Crystal data

[As(C32H16N8)]2[As2I8]	F(000) = 4336
Mr = 2339.94	Dx = 2.246 Mg m^−3 Dm = 2.24 Mg m^−3 Dm measured by flotation in what?
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5312 reflections
a = 19.357 (3) Å	θ = 3.3–28.3°
b = 16.537 (2) Å	µ = 5.54 mm^−1
c = 21.783 (3) Å	T = 295 K
β = 97.09 (1)°	Parallelepiped, black–violet
V = 6919.6 (17) Å^3	0.42 × 0.24 × 0.24 mm
Z = 4

Data collection

Kuma KM-4 CCD area-detector diffractometer	8498 independent reflections
Radiation source: fine-focus sealed tube	5312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	θmax = 28.3°, θmin = 3.3°
ω scans	h = −25→25
Absorption correction: analytical face-indexed, SHELXTL (Sheldrick, 1990b)	k = −22→21
Tmin = 0.212, Tmax = 0.273	l = −28→28
37315 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0806P)^2] where P = (Fo^2 + 2Fc^2)/3
8498 reflections	(Δ/σ)max = 0.001
416 parameters	Δρmax = 1.72 e Å^−3
0 restraints	Δρmin = −1.07 e Å^−3

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
I1	0.41698 (2)	0.56124 (3)	0.47197 (3)	0.06785 (17)
I2	0.35105 (2)	0.78309 (3)	0.52327 (3)	0.06633 (19)
I3	0.29321 (2)	0.69707 (2)	0.350978 (19)	0.06351 (14)
I4	0.22161 (2)	0.49341 (2)	0.42133 (2)	0.06544 (14)
As1	0.29310 (3)	0.63305 (4)	0.45974 (3)	0.05431 (17)
As2	0.10542 (3)	0.62595 (4)	0.33005 (3)	0.06176 (19)
N1	0.0961 (3)	0.7380 (3)	0.2858 (2)	0.0662 (13)
N2	0.1806 (3)	0.7174 (3)	0.2098 (3)	0.0756 (15)
N3	0.1382 (3)	0.5898 (3)	0.2465 (2)	0.0698 (14)
N4	0.1285 (4)	0.4451 (4)	0.2523 (3)	0.100 (2)
N5	0.0565 (3)	0.5150 (4)	0.3213 (3)	0.0810 (17)
N6	−0.0228 (4)	0.5301 (4)	0.3990 (4)	0.102 (2)
N7	0.0141 (3)	0.6605 (3)	0.3588 (3)	0.0718 (15)
N8	0.0182 (3)	0.8074 (4)	0.3476 (3)	0.0729 (16)
C1	0.0643 (4)	0.8042 (4)	0.3088 (3)	0.0677 (16)
C2	0.0916 (4)	0.8770 (4)	0.2812 (3)	0.0732 (18)
C3	0.0769 (4)	0.9563 (5)	0.2882 (4)	0.094 (2)
H3	0.0472	0.9748	0.3156	0.113*
C4	0.1114 (5)	1.0093 (5)	0.2493 (4)	0.094 (3)
H4	0.1045	1.0648	0.2521	0.124*
C5	0.1517 (4)	0.9829 (5)	0.2108 (4)	0.082 (2)
H5	0.1689	1.0202	0.1846	0.098*
C6	0.1717 (5)	0.9010 (5)	0.2055 (3)	0.087 (2)
H6	0.2046	0.8836	0.1809	0.105*
C7	0.1367 (4)	0.8501 (4)	0.2411 (3)	0.0780 (19)
C8	0.1412 (3)	0.7595 (4)	0.2436 (3)	0.0649 (16)
C9	0.1776 (4)	0.6372 (5)	0.2129 (4)	0.086 (2)
C10	0.2162 (4)	0.5879 (4)	0.1734 (3)	0.081 (2)
C11	0.2627 (5)	0.6071 (5)	0.1313 (4)	0.107 (3)
H11	0.2742	0.6605	0.1238	0.140*
C12	0.2906 (5)	0.5451 (5)	0.1017 (4)	0.113 (3)
H12	0.3237	0.5561	0.0753	0.135*
C13	0.2706 (6)	0.4647 (6)	0.1101 (5)	0.102 (4)
H13	0.2900	0.4241	0.0882	0.159*
C14	0.2241 (5)	0.4438 (5)	0.1490 (4)	0.110 (3)
H14	0.2106	0.3903	0.1532	0.133*
C15	0.1962 (5)	0.5086 (5)	0.1837 (3)	0.092 (2)
C16	0.1509 (5)	0.5090 (5)	0.2297 (4)	0.087 (2)
C17	0.0859 (4)	0.4470 (5)	0.2930 (4)	0.086 (2)
C18	0.0578 (5)	0.3741 (5)	0.3231 (5)	0.103 (3)
C19	0.0721 (6)	0.2908 (6)	0.3131 (6)	0.114 (4)
H19	0.1010	0.2722	0.2851	0.161*
C20	0.0361 (7)	0.2393 (6)	0.3519 (6)	0.115 (5)
H20	0.0440	0.1839	0.3499	0.186*
C21	−0.0075 (5)	0.2643 (5)	0.3902 (4)	0.102 (3)
H21	−0.0296	0.2263	0.4125	0.123*
C22	−0.0211 (5)	0.3460 (5)	0.3981 (5)	0.108 (4)
H22	−0.0518	0.3641	0.4247	0.154*
C23	0.0145 (5)	0.3989 (5)	0.3634 (4)	0.098 (2)
C24	0.0127 (4)	0.4859 (5)	0.3626 (4)	0.097 (3)
C25	−0.0236 (4)	0.6133 (5)	0.3953 (4)	0.081 (2)
C26	−0.0670 (4)	0.6603 (5)	0.4276 (4)	0.081 (2)
C27	−0.1143 (4)	0.6411 (5)	0.4688 (4)	0.097 (2)
H27	−0.1220	0.5874	0.4788	0.116*
C28	−0.1499 (5)	0.7028 (5)	0.4949 (4)	0.115 (3)
H28	−0.1818	0.6894	0.5218	0.138*
C29	−0.1389 (5)	0.7869 (5)	0.4816 (4)	0.109 (3)
H29	−0.1616	0.8277	0.5005	0.131*
C30	−0.0908 (4)	0.8051 (5)	0.4374 (4)	0.095 (2)
H30	−0.0831	0.8585	0.4266	0.114*
C31	−0.0571 (4)	0.7441 (5)	0.4119 (4)	0.081 (2)
C32	−0.0064 (3)	0.7390 (5)	0.3692 (3)	0.0706 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0525 (2)	0.0664 (3)	0.0829 (4)	0.01422 (18)	0.0032 (2)	0.0104 (2)
I2	0.0466 (2)	0.0873 (4)	0.0905 (4)	0.0071 (2)	−0.0089 (2)	−0.0611 (3)
I3	0.0793 (3)	0.0473 (2)	0.0610 (3)	−0.00030 (17)	−0.0029 (2)	0.00127 (17)
I4	0.0666 (3)	0.0532 (2)	0.0743 (3)	−0.00597 (17)	0.0001 (2)	0.00410 (18)
As1	0.0494 (3)	0.0634 (4)	0.0481 (3)	0.0078 (2)	−0.0021 (2)	−0.0064 (3)
As2	0.0613 (4)	0.0520 (3)	0.0653 (4)	−0.0123 (3)	−0.0189 (3)	0.0073 (3)
N1	0.059 (3)	0.069 (3)	0.069 (3)	−0.010 (3)	0.001 (3)	0.010 (3)
N2	0.109 (5)	0.063 (3)	0.055 (3)	−0.004 (3)	0.009 (3)	0.003 (3)
N3	0.083 (4)	0.062 (3)	0.059 (3)	−0.009 (3)	−0.012 (3)	0.000 (3)
N4	0.138 (6)	0.099 (5)	0.059 (4)	−0.034 (5)	−0.007 (4)	−0.001 (4)
N5	0.072 (4)	0.072 (4)	0.094 (4)	−0.023 (3)	−0.007 (3)	0.002 (3)
N6	0.073 (4)	0.070 (4)	0.157 (7)	−0.021 (3)	−0.009 (4)	0.031 (4)
N7	0.050 (3)	0.072 (3)	0.088 (4)	−0.008 (2)	−0.013 (3)	0.022 (3)
N8	0.068 (4)	0.068 (4)	0.079 (4)	0.001 (3)	−0.007 (3)	0.008 (3)
C1	0.059 (4)	0.072 (4)	0.071 (4)	−0.006 (3)	0.004 (3)	−0.001 (3)
C2	0.077 (4)	0.070 (4)	0.073 (4)	−0.003 (3)	0.006 (4)	0.014 (3)
C3	0.084 (5)	0.081 (5)	0.116 (7)	0.007 (4)	0.006 (5)	−0.003 (5)
C4	0.106 (8)	0.086 (6)	0.089 (6)	−0.019 (5)	0.012 (6)	0.015 (5)
C5	0.105 (6)	0.070 (4)	0.076 (5)	−0.005 (4)	0.031 (4)	0.018 (4)
C6	0.118 (6)	0.067 (4)	0.078 (5)	−0.005 (4)	0.017 (4)	0.003 (4)
C7	0.078 (5)	0.074 (4)	0.076 (5)	−0.003 (4)	−0.012 (4)	0.010 (4)
C8	0.064 (4)	0.069 (4)	0.056 (3)	−0.009 (3)	0.001 (3)	0.010 (3)
C9	0.107 (6)	0.069 (4)	0.075 (5)	−0.001 (4)	−0.017 (4)	0.006 (4)
C10	0.125 (6)	0.058 (4)	0.055 (4)	0.011 (4)	−0.005 (4)	0.004 (3)
C11	0.136 (10)	0.115 (7)	0.070 (5)	0.044 (7)	0.015 (6)	0.019 (5)
C12	0.154 (9)	0.102 (7)	0.087 (6)	0.015 (6)	0.029 (6)	0.016 (5)
C13	0.133 (12)	0.093 (9)	0.085 (6)	0.026 (8)	0.029 (7)	−0.001 (6)
C14	0.148 (9)	0.100 (7)	0.083 (6)	0.025 (6)	0.011 (6)	0.001 (5)
C15	0.133 (7)	0.078 (5)	0.059 (4)	0.005 (5)	−0.013 (4)	−0.006 (4)
C16	0.118 (6)	0.073 (5)	0.066 (5)	0.001 (4)	0.001 (4)	0.001 (4)
C17	0.089 (5)	0.068 (4)	0.095 (6)	−0.024 (4)	−0.014 (4)	0.003 (4)
C18	0.099 (7)	0.095 (6)	0.107 (7)	−0.011 (5)	−0.023 (5)	−0.004 (5)
C19	0.116 (10)	0.107 (8)	0.120 (10)	−0.021 (7)	0.014 (8)	0.001 (7)
C20	0.111 (10)	0.092 (8)	0.137 (11)	−0.010 (8)	−0.001 (11)	−0.003 (8)
C21	0.080 (5)	0.064 (5)	0.163 (9)	−0.012 (4)	0.014 (6)	0.031 (5)
C22	0.115 (7)	0.089 (7)	0.114 (10)	−0.006 (6)	−0.010 (7)	0.017 (7)
C23	0.096 (6)	0.086 (6)	0.110 (7)	−0.014 (5)	0.006 (5)	0.007 (5)
C24	0.069 (5)	0.084 (6)	0.133 (8)	0.003 (4)	−0.003 (5)	0.019 (5)
C25	0.065 (4)	0.091 (5)	0.086 (5)	−0.015 (4)	0.004 (4)	0.013 (4)
C26	0.064 (4)	0.093 (5)	0.088 (5)	−0.014 (4)	0.018 (4)	0.008 (4)
C27	0.067 (5)	0.104 (6)	0.122 (7)	0.008 (4)	0.019 (5)	0.014 (5)
C28	0.096 (7)	0.109 (7)	0.137 (8)	−0.009 (6)	0.007 (6)	0.010 (6)
C29	0.105 (7)	0.112 (7)	0.109 (7)	0.004 (6)	0.006 (6)	0.001 (6)
C30	0.072 (5)	0.094 (6)	0.116 (7)	−0.002 (4)	−0.003 (5)	0.010 (5)
C31	0.059 (4)	0.096 (6)	0.086 (5)	0.000 (4)	0.002 (4)	0.015 (4)
C32	0.054 (3)	0.082 (5)	0.072 (4)	0.004 (3)	−0.008 (3)	0.018 (4)

Geometric parameters (Å, º)

I1—As1	2.6595 (7)	C9—C10	1.456 (9)
I2—As1	2.9910 (8)	C10—C15	1.394 (10)
I3—As1	2.5953 (8)	C10—C11	1.399 (8)
I4—As1	2.7680 (7)	C11—C12	1.358 (9)
As2—N7	2.028 (6)	C11—H11	0.9300
As2—N5	2.063 (6)	C12—C13	1.403 (11)
As2—N1	2.086 (5)	C12—H12	0.9300
As2—N3	2.088 (6)	C13—C14	1.353 (10)
N1—C1	1.380 (8)	C13—H13	0.9300
N1—C8	1.389 (7)	C14—C15	1.453 (9)
N2—C8	1.323 (7)	C14—H14	0.9300
N2—C9	1.328 (8)	C15—C16	1.412 (10)
N3—C9	1.369 (9)	C17—C18	1.504 (10)
N3—C16	1.414 (8)	C18—C23	1.351 (10)
N4—C16	1.265 (8)	C18—C19	1.427 (10)
N4—C17	1.284 (9)	C19—C20	1.440 (11)
N5—C24	1.395 (8)	C19—H19	0.9300
N5—C17	1.433 (8)	C20—C21	1.324 (9)
N6—C24	1.331 (9)	C20—H20	0.9300
N6—C25	1.379 (8)	C21—C22	1.392 (10)
N7—C25	1.385 (7)	C21—H21	0.9300
N7—C32	1.385 (7)	C22—C23	1.391 (11)
N8—C1	1.303 (7)	C22—H22	0.9300
N8—C32	1.335 (8)	C23—C24	1.439 (10)
C1—C2	1.473 (8)	C25—C26	1.395 (9)
C2—C3	1.354 (9)	C26—C27	1.396 (8)
C2—C7	1.383 (9)	C26—C31	1.447 (8)
C3—C4	1.439 (10)	C27—C28	1.391 (10)
C3—H3	0.9300	C27—H27	0.9300
C4—C5	1.291 (10)	C28—C29	1.441 (10)
C4—H4	0.9300	C28—H28	0.9300
C5—C6	1.416 (9)	C29—C30	1.450 (10)
C5—H5	0.9300	C29—H29	0.9300
C6—C7	1.377 (9)	C30—C31	1.358 (9)
C6—H6	0.9300	C30—H30	0.9300
C7—C8	1.501 (9)	C31—C32	1.434 (9)
I3—As1—I1	99.86 (3)	C11—C12—H12	119.3
I3—As1—I4	96.95 (2)	C13—C12—H12	119.3
I1—As1—I4	93.94 (2)	C14—C13—C12	122.7 (10)
I3—As1—I2	92.38 (2)	C14—C13—H13	118.7
I1—As1—I2	92.41 (2)	C12—C13—H13	118.7
I4—As1—I2	167.65 (3)	C13—C14—C15	117.1 (10)
N7—As2—N5	82.6 (2)	C13—C14—H14	121.5
N7—As2—N1	82.1 (2)	C15—C14—H14	121.5
N5—As2—N1	137.3 (2)	C10—C15—C16	108.6 (7)
N7—As2—N3	136.0 (2)	C10—C15—C14	118.8 (9)
N5—As2—N3	81.4 (2)	C16—C15—C14	132.6 (8)
N1—As2—N3	82.5 (2)	N4—C16—C15	123.0 (8)
C1—N1—C8	112.4 (5)	N4—C16—N3	127.6 (8)
C1—N1—As2	123.6 (4)	C15—C16—N3	109.3 (7)
C8—N1—As2	120.5 (4)	N4—C17—N5	129.7 (7)
C8—N2—C9	117.8 (7)	N4—C17—C18	125.3 (9)
C9—N3—C16	106.1 (7)	N5—C17—C18	104.9 (8)
C9—N3—As2	123.4 (5)	C23—C18—C19	122.6 (10)
C16—N3—As2	125.2 (5)	C23—C18—C17	109.1 (9)
C16—N4—C17	121.9 (8)	C19—C18—C17	128.3 (11)
C24—N5—C17	108.1 (7)	C18—C19—C20	111.4 (12)
C24—N5—As2	123.8 (6)	C18—C19—H19	124.3
C17—N5—As2	122.4 (5)	C20—C19—H19	124.3
C24—N6—C25	121.1 (8)	C21—C20—C19	125.3 (12)
C25—N7—C32	104.5 (6)	C21—C20—H20	117.4
C25—N7—As2	124.0 (5)	C19—C20—H20	117.4
C32—N7—As2	126.4 (4)	C20—C21—C22	121.7 (9)
C1—N8—C32	119.8 (6)	C20—C21—H21	119.2
N8—C1—N1	129.8 (6)	C22—C21—H21	119.2
N8—C1—C2	122.7 (6)	C21—C22—C23	115.5 (10)
N1—C1—C2	107.6 (6)	C21—C22—H22	122.3
C3—C2—C7	122.7 (7)	C23—C22—H22	122.3
C3—C2—C1	130.9 (7)	C18—C23—C22	123.5 (9)
C7—C2—C1	106.3 (6)	C18—C23—C24	108.1 (8)
C2—C3—C4	113.9 (9)	C22—C23—C24	128.5 (9)
C2—C3—H3	123.1	N6—C24—N5	126.5 (7)
C4—C3—H3	123.1	N6—C24—C23	123.7 (8)
C5—C4—C3	122.5 (9)	N5—C24—C23	109.7 (7)
C5—C4—H4	118.7	N6—C25—N7	126.4 (8)
C3—C4—H4	118.7	N6—C25—C26	121.9 (7)
C4—C5—C6	124.7 (7)	N7—C25—C26	111.6 (7)
C4—C5—H5	117.7	C25—C26—C27	132.9 (8)
C6—C5—H5	117.7	C25—C26—C31	108.0 (6)
C7—C6—C5	112.4 (8)	C27—C26—C31	119.1 (8)
C7—C6—H6	123.8	C28—C27—C26	119.6 (9)
C5—C6—H6	123.8	C28—C27—H27	120.2
C6—C7—C2	123.4 (7)	C26—C27—H27	120.2
C6—C7—C8	127.0 (8)	C27—C28—C29	122.1 (10)
C2—C7—C8	109.6 (6)	C27—C28—H28	118.9
N2—C8—N1	133.3 (6)	C29—C28—H28	118.9
N2—C8—C7	122.7 (6)	C28—C29—C30	117.2 (9)
N1—C8—C7	104.1 (6)	C28—C29—H29	121.4
N2—C9—N3	129.0 (8)	C30—C29—H29	121.4
N2—C9—C10	120.0 (8)	C31—C30—C29	119.8 (8)
N3—C9—C10	110.8 (7)	C31—C30—H30	120.1
C15—C10—C11	122.1 (8)	C29—C30—H30	120.1
C15—C10—C9	105.0 (7)	C30—C31—C32	135.3 (8)
C11—C10—C9	132.8 (8)	C30—C31—C26	122.1 (7)
C12—C11—C10	117.8 (10)	C32—C31—C26	102.6 (7)
C12—C11—H11	121.1	N8—C32—N7	127.8 (7)
C10—C11—H11	121.1	N8—C32—C31	118.8 (7)
C11—C12—C13	121.4 (10)	N7—C32—C31	113.2 (6)