Tetrakis­[phthalocyaninato(2-)­antimony(III)] hexadecaiodotetraantimony(III)

Crystals of a new antimony(III) phthalocyanine complex with the formula [Sb(C₃₂H₁₆N₈)]₄(Sb₄I₁₆), or (SbPc)·[Sb₄I₁₆]^4-, where Pc is phthalocyaninate, have been obtained by the reaction of pure powdered antimony with phthalo­nitrile under a stream of iodine vapour. The crystals are built up from separate but interacting (SbPc)⁺ cations and centrosymmetric [Sb₄I₁₆]^4- anions. Each Sb atom of two independent (SbPc)⁺ units is bonded to the four iso­indole N atoms of the phthalocyaninate(2-) macrocycle and lies 1.0 Å out of the plane defined by four iso­indole N atoms. The anionic part of the complex consists of four SbI₆ distorted octahedra joined together into a centrosymmetric [Sb₄I₁₆]^4- anion. The arrangement of oppositely charged moieties in the crystal is mainly determined by ionic attraction and by a set of distinct donor-acceptor interactions between (SbPc)⁺ and [Sb₄I₁₆]^4- ions.

S1. Comment

This study is a part of our investigation on syntheses and characterization of iodine-doped metallophthalocyanines. Earlier, we reported that besides the well characterized iodine-doped metallophthalocyanines and diphthalocyanines, in which the iodine-doped atoms form chains of disordered symmetrical triiodide ions (Janczak et al., 1998; Janczak, Kubiak & Jezierski, 1999; Janczak, Kubiak, Svoboda et al., 2000; Janczak & Kubiak, 1999a; Janczak & Idemori, 2001a) and metallophthalocyanines in which the iodine atoms are directly joined to the central metal ion yielding mono- or diiodometallophthalocyanine complexes (Janczak & Kubiak, 1999b, 1999c; Janczak & Idemori, 2001b) as well as the iodine atoms can form a neutral I₂ molecule which is a bridge for dimerization of monoiodometallophthalocyanines (Janczak, Kubiak & Hahn, 1999) or for developing a polymeric supramolecular structure of diiodometallophthalocyanines (Janczak, Razik & Kubiak, 1999) are formed. Quite recently we reported that depending on the condition of the synthesis the iodine-doped atoms could form ordered but unsymmetrical triiodide ions (Janczak & Kubiak, 1999 d; Kubiak et al., 1999; Janczak & Idemori, 2001c). This antimony(III) phthalocyanine–antimony(III) iodine complex, [(SbPc)₄(Sb₄I₁₆)], is isostructural with the bismuth(III) analogue, [(BiPc)₄(Bi₄I₁₆)], (Kubiak & Ejsmont, 1999) and to our knowledge it is the second structurally characterized phthalocyaninato compound which contain the same metal in both ionic part of the complex, i.e. in (SbPc)⁺ as well as in [Sb₄I₁₆]^4-.

The crystal of the title compound is built up from separate but interacting units of (SbPc)⁺and (Sb₄I₁₆)^4- (Fig.1). The two crystallographically independent (SbPc)⁺ cation-units have essentially the same geometry. In both SbPc cation moieties each of the phthalocyaninato(2-) macrocycle shows saucer-shaped form, as a result of the interaction of the central antimony(III) ion with the oppositely charged (Sb₄I₁₆)^4- unit. The greatest deviation from the planes defined by four isoindole nitrogen atoms of the Pc macrocycles is observed for the outermost carbon atoms of the phenyl rings C26—C31 (0.157 (3) - 0.464 (3) Å) and C34—C39 [0.286 (3)–0.634 (3) Å] for Sb1Pc and Sb2Pc units, respectively. The positively charged Sb1 and Sb2 atoms are significantly displaced from the N₄-isoindole planes towards to the iodine atoms of the (Sb₄I₁₆)^4- counter ion. The displacements of Sb1 and Sb2 are almost equal, 0.999 (3) Å for Sb1 and 1.010 (3) Å for Sb2. This is quite reasonable because the ionic radius of antimony(III) [about 0.90 Å] is too large to be fitted inside the cavity of the phthalocyaninato(2-) macrocycle (Shannon, 1976), as well as due to the ionic attraction between the positively charged antimony(III) atoms with iodine atoms of (Sb₄I₁₆)^4-. The influence of the interaction is clearly manifested in the Sb—N_isoindole coordination leading to the molecular symmetry of the Sb—N core close to C_s and not to C_4v. A similar deviation of antimony(III) ion from the N₄-isoindole plane has been observed in other iodine-doped antimony(III) monophthalocyaninato complexes (Kubiak & Razik, 1998; Kubiak et al., 1999). However, in diphthalocyaninato(2-) antimony(III) complexes, in which the antimony(III) is sandwiched between two phthalocyaninato macrocycles, the displacement of the antimony(III) of about 1.45 Å is mainly determined by the Pc—Pc interaction of the SbPc₂ units, for instance in (n-Bu₄N)[Sb(III)Pc₂]^.2THF and (PNP)₂[Sb(III)Pc₂]Br^.2Et₂O, which are the two sandwich type antimony(III) diphthalocyaninato(2-) complexes, that have been recently structurally characterized (Hückstädt et al., 2001). For a comparison the deviation of the bismuth(III) cation from the N₄-isoindole plane in the isostructural bismuth(III) analogue complex is equal to 1.137 (7) Å (Kubiak & Ejsmont, 1999). The difference between the displacemnt of the antimony(III) and bismuth(III) cations from the N₄-planes of the Pc macrorings is consistent with the difference between their ionic radii (Shannon, 1976).

The anionic part of the complex consists of four SbI₆ deformed octahedra joined together into a centrosymmetric (Sb₄I₁₆)^4- counter ion. The Sb—I bond lengths fall into two groups: shorter Sb—I bonds with the terminal iodine and longer with the bridging iodine. However in the (Sb₄I₁₆)^4- anionic complex two different bridging iodine atoms exist. The I2 nd I3 atoms are bridging two antimony ions, while the I1 is a bridge for the three antimony ions. The distortion of the SbI₆ polyhedron from the O_h symmetry is likely due to the lone electron pair on the antimony ion. Looking in more details on the differences between the Sb—I bond lengths as well as on the coordination geometry arround the antimony Sb3 and Sb4 atoms (and symmetrically equivalents), it is clear that they have different coordination. The Sb3 atom joins five iodine atoms with relatively short Sb—I bonds, the sixth Sb—-I bond length is relatively long. In the coordination sphere of the second antimony, Sb4, three short Sb—I bonds and three relatively long Sb—I bonds are observed. Concluding, it could be said that the (Sb₄I₁₆)^4- counter ion is composed from two pair of symmetrically equivalent units: (SbI₅)^2- and SbI₃. The antimony Sb3 atom in (SbI₅)^2- ion have distorted square pyramidal coordination, four iodine atoms in plane (I1, I2, I3 and I4) and one apical I5 atom. The relatively long Sb3—I1ⁱ bond in trans position to the apical iodine atom indicates the stereochemical effect of the electron lone pair. In the coordination sphere of Sb4 atom it is not clear in which direction the electron lone pair points, since three relative long Sb—I bond lengths are very similar. However, the mutual orientation of both (SbI₅)^2- and SbI₃ units related by inversion center in the crystal leads to the formation of a [Sb₄I₁₆]^4- counter ion. A similar pattern of short and long M—I bond lengths is observed in the [Bi₄I₁₆]^4-ion of the bismuth(III) phthalocyaninato analogue complex, but no comment was made on this fact (Kubiak & Ejsmont, 1999).

In the unit cell (Fig. 2) there seems to be significant ionic attraction between the (SbPc)⁺ and (Sb₄I₁₆)^4- counter ion. Each (Sb₄I₁₆)^4- anion is surrounded by four (SbPc)⁺ units. The Sb1 and Sb2 atoms of the (SbPc)⁺ moieties interact with three iodine atoms of (Sb₄I₁₆)^4- (Sb1 with I4, I6 and I1, while Sb2 with I2, I4 and I5) since the Sb—I contacts are shorter than 4.35 Å from the antimony atoms, that value being the sum of the van der Waals radii of antimony and iodine (Pauling, 1960). The dihedral angle between mean planes through the Pc-macrocycle of (Sb1Pc)⁺ and (Sb2Pc)⁺ units is equal to 106.4°. The centrosymmetric [(SbPc)₄(Sb₄I₁₆)] aggregates in the crystal form π—π interacted stacks in back-to-back manner of the Pc-macrocycle. The back-to-back distance in the stack of two neighbouring [(SbPc)₄(Sb₄I₁₆)] molecules is shorter than 3.0 Å. This value indicates on the interaction and overlaping of the π-clouds of phthalocyaninato macrocycle. The π—π intermolecular interaction is a common feature in the field of phthalocyanine chemistry, since the phthalocyanine and its metal complexes tend to aggregate the molecules to each other due to the strong π—π interaction (Nevin et al., 1987; Terekhov et al., 1996; Isago et al., 1997, 1998).

Although the crystals of [(SbPc)₄(Sb₄I₁₆)] are built up from the opposite charged (SbPc)⁺ and (Sb₄I₁₆)^4- ions, the compound does not posses the characteristic properties of the ionic crystals. The solubility of this compound in the polar solvents as water, methanol, ethanol etc is insignificant and it is slightly soluble in pyridine, DMSO, THF and chloronaphthalene. As can be seen from the crystal structure architecture of [(SbPc)₄(Sb₄I₁₆)] both hydrophilic parts of this complex in the crystal are surrounded by a hydrophobic peripheral phenyl rings of the Pc macrocycle.

S2. Experimental

The crystals of [(SbPc)₄(Sb₄I₁₆)] were obtained by the direct reaction of the pure powdered arsenic with phthalonitrile (Kubiak & Janczak, 1993) under a stream of iodine vapours at 513 K.

The measurement has been performed on a KUMA KM-4 diffractometer equipped with a two-dimension area CCD detector. The ω-scan technique was used, the Δω = 0.75° for one image. The 960 images for six different runs covered about 95% of the Ewald sphere. The lattice parameters were calculated using 458 reflections obtained from 50 images for 10 runs with different orientations in reciprocal space and after data collection were refined on 10265 reflections.

Computing details

Data collection: KUMA KM-4 CCD software (Kuma Diffraction, 1999); cell refinement: KUMA KM-4 CCD software (Kuma Diffraction, 1999); data reduction: KUMA KM-4 CCD software (Kuma Diffraction, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. Molecular structure showing 50% probability displacement ellipsoids (a) two independent SbPc^+ units and (b) [Sb4I16]^4- counter ion [symmetry code: (i) 1 - x, 1 - y, -z]. H atoms are shown as spheres of an arbitrary radius.
	Fig. 2. Molecular packing in the unit cell showing the Sb···I interaction (dashed lines).

Tetrakis(phthalocyaninato(2-)antimony(III) hexadecaiodotetraantimony(III)

Crystal data

[(C32H16N8)Sb]4[Sb4I16]	F(000) = 2312
Mr = 5054.62	Dx = 2.421 Mg m^−3 Dm = 2.42 Mg m^−3 Dm measured by floatation
Triclinic, P1	Melting point: decomposition K
a = 15.963 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.051 (3) Å	Cell parameters from 10265 reflections
c = 16.552 (3) Å	θ = 3–27°
α = 88.59 (3)°	µ = 5.16 mm^−1
β = 62.54 (3)°	T = 293 K
γ = 69.16 (3)°	Parallelepiped, dark-violet
V = 3466.9 (11) Å^3	0.20 × 0.12 × 0.08 mm
Z = 1

Data collection

KUMA KM-4 with two dimensional area CCD detector diffractometer	14695 independent reflections
Radiation source: fine-focus sealed tube	10265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	θmax = 27.2°, θmin = 2.8°
ω–scan	h = −20→17
Absorption correction: analytical face-indexed, SHELXTL (Sheldrick, 1990)	k = −20→20
Tmin = 0.425, Tmax = 0.683	l = −21→21
29594 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.0131P] where P = (Fo^2 + 2Fc^2)/3
14695 reflections	(Δ/σ)max = 0.002
829 parameters	Δρmax = 1.21 e Å^−3
0 restraints	Δρmin = −1.17 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	0.44173 (3)	0.50667 (2)	−0.08872 (2)	0.04754 (9)
I2	0.32763 (3)	0.76097 (2)	0.09585 (3)	0.04782 (10)
I3	0.31639 (4)	0.39256 (3)	0.15588 (3)	0.07056 (13)
I4	0.21661 (3)	0.62902 (2)	0.33004 (2)	0.05142 (10)
I5	0.11982 (3)	0.65177 (3)	0.13332 (4)	0.07356 (14)
I6	0.46698 (3)	0.74273 (2)	0.26448 (3)	0.05999 (11)
I7	0.54873 (4)	0.87614 (3)	0.03333 (4)	0.07912 (15)
I8	0.75696 (4)	0.64200 (4)	0.05513 (5)	0.09866 (19)
Sb3	0.31258 (3)	0.57793 (2)	0.12772 (2)	0.03965 (9)
Sb4	0.56431 (3)	0.70030 (2)	0.06838 (3)	0.04799 (10)
Sb1	0.45956 (2)	0.52091 (2)	0.33145 (2)	0.03776 (9)
N1	0.6171 (3)	0.4845 (3)	0.3025 (3)	0.0460 (11)
N2	0.5977 (3)	0.6162 (3)	0.3904 (3)	0.0495 (11)
N3	0.4381 (3)	0.5932 (3)	0.4545 (3)	0.0424 (10)
N4	0.2614 (3)	0.6145 (3)	0.5614 (3)	0.0452 (11)
N5	0.3452 (3)	0.4804 (2)	0.4442 (3)	0.0377 (9)
N6	0.3667 (4)	0.3458 (3)	0.3611 (3)	0.0485 (11)
N7	0.5225 (3)	0.3741 (3)	0.2900 (3)	0.0462 (11)
N8	0.7015 (4)	0.3462 (3)	0.1901 (3)	0.0546 (12)
C1	0.6992 (4)	0.4179 (4)	0.2290 (4)	0.0550 (15)
C2	0.7880 (4)	0.4396 (5)	0.2012 (5)	0.0654 (17)
C3	0.8881 (6)	0.3976 (6)	0.1289 (6)	0.103 (3)
H3	0.9085	0.3443	0.0913	0.124*
C4	0.9538 (6)	0.4373 (8)	0.1159 (7)	0.126 (4)
H4	1.0203	0.4111	0.0670	0.151*
C5	0.9269 (6)	0.5162 (8)	0.1725 (8)	0.124 (4)
H5	0.9754	0.5406	0.1610	0.148*
C6	0.8279 (5)	0.5584 (6)	0.2459 (6)	0.091 (2)
H6	0.8089	0.6106	0.2842	0.109*
C7	0.7587 (4)	0.5191 (5)	0.2594 (4)	0.0647 (17)
C8	0.6509 (4)	0.5456 (4)	0.3222 (4)	0.0499 (14)
C9	0.4985 (4)	0.6376 (4)	0.4519 (4)	0.0434 (12)
C10	0.4409 (4)	0.7132 (4)	0.5260 (4)	0.0465 (13)
C11	0.4647 (5)	0.7810 (4)	0.5542 (4)	0.0534 (15)
H11	0.5303	0.7809	0.5235	0.064*
C12	0.3877 (5)	0.8458 (4)	0.6279 (4)	0.0597 (16)
H12	0.4006	0.8929	0.6447	0.072*
C13	0.2904 (5)	0.8443 (4)	0.6792 (4)	0.0589 (16)
H13	0.2411	0.8883	0.7309	0.071*
C14	0.2663 (5)	0.7775 (4)	0.6535 (4)	0.0526 (14)
H14	0.2014	0.7763	0.6873	0.063*
C15	0.3417 (4)	0.7131 (3)	0.5765 (4)	0.0429 (12)
C16	0.3421 (4)	0.6367 (3)	0.5300 (4)	0.0416 (12)
C17	0.2642 (4)	0.5418 (3)	0.5208 (4)	0.0396 (12)
C18	0.1776 (4)	0.5154 (3)	0.5557 (4)	0.0467 (13)
C19	0.0790 (4)	0.5542 (4)	0.6316 (5)	0.074 (2)
H19	0.0580	0.6061	0.6714	0.089*
C20	0.0151 (5)	0.5098 (5)	0.6432 (6)	0.095 (3)
H20	−0.0523	0.5348	0.6907	0.114*
C21	0.0461 (6)	0.4316 (5)	0.5884 (6)	0.096 (3)
H21	0.0003	0.4038	0.6012	0.116*
C22	0.1427 (5)	0.3926 (4)	0.5152 (5)	0.0713 (19)
H22	0.1631	0.3390	0.4781	0.086*
C23	0.2093 (4)	0.4359 (4)	0.4981 (4)	0.0507 (14)
C24	0.3141 (4)	0.4165 (3)	0.4286 (4)	0.0424 (12)
C25	0.4639 (4)	0.3252 (3)	0.2980 (4)	0.0474 (13)
C26	0.5251 (5)	0.2443 (3)	0.2302 (4)	0.0537 (15)
C27	0.5030 (5)	0.1736 (4)	0.2101 (4)	0.0666 (18)
H27	0.4372	0.1741	0.2421	0.080*
C28	0.5814 (8)	0.1034 (4)	0.1416 (5)	0.089 (3)
H28	0.5688	0.0552	0.1268	0.107*
C29	0.6805 (7)	0.1032 (5)	0.0933 (5)	0.086 (3)
H29	0.7327	0.0540	0.0480	0.103*
C30	0.7025 (5)	0.1730 (4)	0.1109 (4)	0.071 (2)
H30	0.7679	0.1732	0.0774	0.086*
C31	0.6232 (5)	0.2440 (3)	0.1809 (4)	0.0530 (15)
C32	0.6204 (5)	0.3269 (3)	0.2193 (4)	0.0480 (14)
Sb2	0.08550 (2)	0.84664 (2)	0.29813 (2)	0.03758 (9)
N9	0.0008 (3)	0.8539 (3)	0.4495 (3)	0.0418 (10)
N10	0.1174 (3)	0.8741 (3)	0.4958 (3)	0.0441 (10)
N11	0.1461 (3)	0.9241 (3)	0.3472 (3)	0.0408 (10)
N12	0.2069 (3)	1.0012 (3)	0.2163 (3)	0.0450 (11)
N13	0.0685 (3)	0.9636 (3)	0.2273 (3)	0.0423 (10)
N14	−0.0674 (3)	0.9640 (3)	0.1953 (3)	0.0478 (11)
N15	−0.0750 (3)	0.8892 (3)	0.3263 (3)	0.0414 (10)
N16	−0.1394 (3)	0.8176 (3)	0.4606 (3)	0.0460 (11)
C33	−0.0790 (4)	0.8250 (3)	0.4916 (4)	0.0396 (12)
C34	−0.0898 (4)	0.8028 (3)	0.5799 (4)	0.0402 (12)
C35	−0.1584 (4)	0.7731 (3)	0.6519 (4)	0.0494 (14)
H35	−0.2113	0.7648	0.6480	0.059*
C36	−0.1452 (5)	0.7567 (4)	0.7281 (4)	0.0620 (17)
H36	−0.1891	0.7362	0.7757	0.074*
C37	−0.0671 (5)	0.7703 (4)	0.7353 (4)	0.0609 (17)
H37	−0.0603	0.7583	0.7877	0.073*
C38	−0.0002 (4)	0.8008 (3)	0.6674 (4)	0.0484 (14)
H38	0.0508	0.8107	0.6733	0.058*
C39	−0.0117 (4)	0.8164 (3)	0.5886 (3)	0.0430 (13)
C40	0.0422 (4)	0.8497 (3)	0.5075 (4)	0.0452 (13)
C41	0.1645 (4)	0.9088 (3)	0.4209 (4)	0.0412 (12)
C42	0.2399 (4)	0.9433 (3)	0.4123 (4)	0.0531 (15)
C43	0.2854 (4)	0.9430 (4)	0.4660 (5)	0.0570 (15)
H43	0.2665	0.9194	0.5206	0.068*
C44	0.3603 (5)	0.9790 (4)	0.4366 (5)	0.0593 (16)
H44	0.3923	0.9795	0.4713	0.071*
C45	0.3866 (5)	1.0142 (4)	0.3546 (5)	0.0672 (18)
H45	0.4362	1.0386	0.3368	0.081*
C46	0.3441 (4)	1.0155 (4)	0.2980 (5)	0.0562 (16)
H46	0.3638	1.0388	0.2432	0.067*
C47	0.2680 (4)	0.9784 (3)	0.3306 (4)	0.0455 (13)
C48	0.2061 (4)	0.9688 (3)	0.2910 (4)	0.0441 (13)
C49	0.1404 (4)	1.0024 (3)	0.1902 (4)	0.0398 (12)
C50	0.1252 (4)	1.0540 (3)	0.1214 (4)	0.0430 (12)
C51	0.1741 (5)	1.1067 (4)	0.0671 (4)	0.0543 (15)
H51	0.2292	1.1121	0.0692	0.065*
C52	0.1386 (5)	1.1506 (4)	0.0103 (4)	0.0628 (17)
H52	0.1693	1.1873	−0.0258	0.075*
C53	0.0588 (5)	1.1414 (4)	0.0058 (4)	0.0648 (18)
H53	0.0373	1.1717	−0.0341	0.078*
C54	0.0091 (5)	1.0888 (4)	0.0584 (4)	0.0639 (17)
H54	−0.0456	1.0835	0.0553	0.077*
C55	0.0451 (4)	1.0439 (3)	0.1165 (3)	0.0429 (12)
C56	0.0095 (4)	0.9866 (3)	0.1822 (4)	0.0418 (12)
C57	−0.1058 (4)	0.9194 (3)	0.2626 (4)	0.0432 (13)
C58	−0.1910 (4)	0.8941 (3)	0.2782 (4)	0.0453 (13)
C59	−0.2489 (5)	0.9088 (4)	0.2340 (4)	0.0566 (15)
H59	−0.2374	0.9414	0.1855	0.068*
C60	−0.3245 (5)	0.8740 (5)	0.2633 (5)	0.0712 (19)
H60	−0.3638	0.8824	0.2340	0.085*
C61	−0.3412 (5)	0.8251 (5)	0.3385 (5)	0.074 (2)
H61	−0.3904	0.8004	0.3568	0.089*
C62	−0.2866 (5)	0.8139 (4)	0.3843 (4)	0.0635 (17)
H62	−0.2997	0.7837	0.4347	0.076*
C63	−0.2102 (4)	0.8488 (4)	0.3537 (4)	0.0460 (13)
C64	−0.1385 (4)	0.8496 (3)	0.3844 (4)	0.0423 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0546 (2)	0.04202 (18)	0.0429 (2)	−0.01792 (16)	−0.02194 (18)	0.01002 (15)
I2	0.0411 (2)	0.03921 (17)	0.0586 (2)	−0.01824 (15)	−0.01892 (18)	0.01487 (16)
I3	0.0798 (3)	0.0481 (2)	0.0678 (3)	−0.0346 (2)	−0.0166 (2)	0.0189 (2)
I4	0.0397 (2)	0.0562 (2)	0.0433 (2)	−0.00805 (16)	−0.01647 (17)	0.01290 (17)
I5	0.0574 (3)	0.0805 (3)	0.0984 (4)	−0.0294 (2)	−0.0476 (3)	0.0093 (3)
I6	0.0696 (3)	0.0444 (2)	0.0645 (3)	−0.01706 (19)	−0.0349 (2)	0.00688 (18)
I7	0.0756 (3)	0.0481 (2)	0.1133 (4)	−0.0355 (2)	−0.0377 (3)	0.0260 (2)
I8	0.0435 (3)	0.0903 (4)	0.1557 (6)	−0.0254 (2)	−0.0438 (3)	0.0210 (3)
Sb3	0.03525 (19)	0.03459 (16)	0.0422 (2)	−0.01349 (14)	−0.01344 (16)	0.00644 (14)
Sb4	0.0358 (2)	0.03883 (18)	0.0621 (2)	−0.01751 (15)	−0.01591 (18)	0.00777 (17)
Sb1	0.03278 (18)	0.03495 (16)	0.04061 (19)	−0.01089 (14)	−0.01567 (16)	0.00776 (14)
N1	0.031 (2)	0.056 (3)	0.036 (2)	−0.012 (2)	−0.008 (2)	0.003 (2)
N2	0.043 (3)	0.065 (3)	0.048 (3)	−0.028 (2)	−0.023 (2)	0.015 (2)
N3	0.036 (2)	0.045 (2)	0.046 (3)	−0.022 (2)	−0.014 (2)	0.008 (2)
N4	0.036 (2)	0.042 (2)	0.051 (3)	−0.0175 (19)	−0.015 (2)	0.002 (2)
N5	0.035 (2)	0.033 (2)	0.038 (2)	−0.0112 (17)	−0.013 (2)	0.0046 (18)
N6	0.056 (3)	0.039 (2)	0.047 (3)	−0.019 (2)	−0.023 (2)	0.009 (2)
N7	0.047 (3)	0.038 (2)	0.040 (3)	−0.008 (2)	−0.016 (2)	0.0007 (19)
N8	0.047 (3)	0.047 (3)	0.044 (3)	−0.006 (2)	−0.011 (2)	0.006 (2)
C1	0.036 (3)	0.066 (4)	0.050 (4)	−0.008 (3)	−0.019 (3)	0.022 (3)
C2	0.033 (3)	0.077 (4)	0.071 (4)	−0.016 (3)	−0.018 (3)	0.017 (4)
C3	0.050 (5)	0.107 (6)	0.108 (7)	−0.022 (4)	−0.009 (5)	0.001 (5)
C4	0.048 (5)	0.146 (9)	0.119 (8)	−0.033 (6)	0.009 (5)	−0.008 (7)
C5	0.052 (5)	0.151 (9)	0.161 (10)	−0.058 (6)	−0.033 (6)	0.034 (8)
C6	0.047 (4)	0.120 (6)	0.117 (7)	−0.047 (4)	−0.038 (5)	0.034 (5)
C7	0.039 (3)	0.088 (5)	0.063 (4)	−0.030 (3)	−0.018 (3)	0.031 (4)
C8	0.035 (3)	0.063 (4)	0.055 (4)	−0.020 (3)	−0.025 (3)	0.023 (3)
C9	0.035 (3)	0.052 (3)	0.047 (3)	−0.022 (2)	−0.019 (3)	0.012 (3)
C10	0.054 (4)	0.051 (3)	0.046 (3)	−0.027 (3)	−0.029 (3)	0.020 (3)
C11	0.076 (4)	0.063 (4)	0.057 (4)	−0.050 (3)	−0.044 (3)	0.034 (3)
C12	0.085 (5)	0.048 (3)	0.066 (4)	−0.033 (3)	−0.047 (4)	0.008 (3)
C13	0.080 (5)	0.050 (3)	0.053 (4)	−0.015 (3)	−0.044 (4)	0.004 (3)
C14	0.054 (4)	0.047 (3)	0.054 (4)	−0.013 (3)	−0.028 (3)	0.010 (3)
C15	0.049 (3)	0.033 (2)	0.054 (3)	−0.016 (2)	−0.030 (3)	0.011 (2)
C16	0.033 (3)	0.040 (3)	0.047 (3)	−0.015 (2)	−0.016 (3)	0.009 (2)
C17	0.031 (3)	0.036 (3)	0.045 (3)	−0.011 (2)	−0.014 (2)	0.008 (2)
C18	0.042 (3)	0.037 (3)	0.058 (3)	−0.021 (2)	−0.018 (3)	0.006 (2)
C19	0.038 (3)	0.057 (4)	0.097 (5)	−0.023 (3)	−0.005 (4)	−0.004 (4)
C20	0.047 (4)	0.064 (4)	0.130 (7)	−0.029 (3)	−0.001 (4)	−0.011 (4)
C21	0.071 (5)	0.087 (5)	0.141 (8)	−0.059 (5)	−0.039 (5)	0.016 (5)
C22	0.072 (5)	0.050 (3)	0.092 (5)	−0.043 (3)	−0.027 (4)	0.010 (3)
C23	0.048 (3)	0.046 (3)	0.057 (4)	−0.022 (3)	−0.022 (3)	0.005 (3)
C24	0.049 (3)	0.032 (2)	0.049 (3)	−0.017 (2)	−0.024 (3)	0.011 (2)
C25	0.052 (4)	0.042 (3)	0.048 (3)	−0.015 (3)	−0.027 (3)	0.016 (3)
C26	0.074 (4)	0.034 (3)	0.047 (3)	−0.011 (3)	−0.032 (3)	0.008 (2)
C27	0.083 (5)	0.051 (3)	0.054 (4)	−0.013 (3)	−0.033 (4)	0.001 (3)
C28	0.153 (8)	0.049 (4)	0.066 (5)	−0.031 (5)	−0.059 (6)	0.010 (4)
C29	0.121 (7)	0.050 (4)	0.056 (5)	−0.002 (4)	−0.041 (5)	−0.008 (3)
C30	0.081 (5)	0.056 (4)	0.037 (3)	0.007 (3)	−0.022 (3)	0.004 (3)
C31	0.068 (4)	0.038 (3)	0.038 (3)	−0.005 (3)	−0.026 (3)	0.012 (2)
C32	0.051 (4)	0.039 (3)	0.043 (3)	−0.004 (3)	−0.024 (3)	0.013 (2)
Sb2	0.03268 (18)	0.03033 (16)	0.0430 (2)	−0.01266 (13)	−0.01278 (16)	0.00555 (14)
N9	0.034 (2)	0.035 (2)	0.054 (3)	−0.0149 (18)	−0.018 (2)	0.0117 (19)
N10	0.038 (3)	0.041 (2)	0.049 (3)	−0.014 (2)	−0.019 (2)	0.006 (2)
N11	0.035 (2)	0.039 (2)	0.050 (3)	−0.0199 (19)	−0.018 (2)	0.014 (2)
N12	0.040 (3)	0.033 (2)	0.055 (3)	−0.0176 (19)	−0.015 (2)	0.007 (2)
N13	0.036 (2)	0.038 (2)	0.046 (3)	−0.0168 (19)	−0.013 (2)	0.0134 (19)
N14	0.040 (3)	0.045 (2)	0.055 (3)	−0.017 (2)	−0.021 (2)	0.009 (2)
N15	0.026 (2)	0.046 (2)	0.046 (3)	−0.0182 (19)	−0.010 (2)	0.011 (2)
N16	0.041 (3)	0.043 (2)	0.048 (3)	−0.020 (2)	−0.015 (2)	0.009 (2)
C33	0.036 (3)	0.031 (2)	0.043 (3)	−0.011 (2)	−0.014 (2)	0.005 (2)
C34	0.034 (3)	0.031 (2)	0.046 (3)	−0.010 (2)	−0.013 (2)	0.007 (2)
C35	0.049 (3)	0.037 (3)	0.051 (3)	−0.020 (2)	−0.013 (3)	0.003 (2)
C36	0.077 (5)	0.042 (3)	0.043 (4)	−0.023 (3)	−0.010 (3)	0.003 (3)
C37	0.083 (5)	0.039 (3)	0.040 (3)	−0.013 (3)	−0.021 (3)	0.002 (3)
C38	0.052 (3)	0.044 (3)	0.039 (3)	−0.014 (3)	−0.017 (3)	0.002 (2)
C39	0.042 (3)	0.038 (3)	0.036 (3)	−0.015 (2)	−0.010 (2)	−0.001 (2)
C40	0.033 (3)	0.048 (3)	0.048 (3)	−0.018 (2)	−0.014 (3)	0.006 (2)
C41	0.034 (3)	0.030 (2)	0.052 (3)	−0.010 (2)	−0.016 (3)	−0.002 (2)
C42	0.044 (3)	0.036 (3)	0.069 (4)	−0.009 (2)	−0.024 (3)	−0.004 (3)
C43	0.051 (4)	0.056 (3)	0.071 (4)	−0.021 (3)	−0.035 (3)	0.006 (3)
C44	0.055 (4)	0.064 (4)	0.077 (5)	−0.027 (3)	−0.043 (4)	0.014 (3)
C45	0.049 (4)	0.063 (4)	0.102 (6)	−0.027 (3)	−0.042 (4)	0.017 (4)
C46	0.046 (3)	0.046 (3)	0.086 (5)	−0.022 (3)	−0.037 (3)	0.016 (3)
C47	0.035 (3)	0.029 (2)	0.064 (4)	−0.008 (2)	−0.020 (3)	−0.002 (2)
C48	0.028 (3)	0.034 (3)	0.058 (4)	−0.008 (2)	−0.013 (3)	0.004 (2)
C49	0.031 (3)	0.031 (2)	0.050 (3)	−0.015 (2)	−0.011 (2)	0.009 (2)
C50	0.041 (3)	0.036 (3)	0.041 (3)	−0.014 (2)	−0.011 (3)	0.000 (2)
C51	0.071 (4)	0.044 (3)	0.043 (3)	−0.036 (3)	−0.013 (3)	0.010 (3)
C52	0.088 (5)	0.050 (3)	0.046 (4)	−0.041 (3)	−0.020 (4)	0.008 (3)
C53	0.092 (5)	0.054 (3)	0.046 (4)	−0.034 (4)	−0.028 (4)	0.019 (3)
C54	0.074 (4)	0.053 (3)	0.060 (4)	−0.023 (3)	−0.031 (4)	0.014 (3)
C55	0.041 (3)	0.033 (2)	0.039 (3)	−0.012 (2)	−0.009 (3)	0.006 (2)
C56	0.032 (3)	0.033 (2)	0.051 (3)	−0.010 (2)	−0.015 (3)	0.005 (2)
C57	0.032 (3)	0.040 (3)	0.054 (3)	−0.016 (2)	−0.016 (3)	0.012 (3)
C58	0.033 (3)	0.046 (3)	0.052 (3)	−0.016 (2)	−0.016 (3)	0.005 (3)
C59	0.056 (4)	0.070 (4)	0.048 (3)	−0.027 (3)	−0.028 (3)	0.015 (3)
C60	0.056 (4)	0.098 (5)	0.078 (5)	−0.043 (4)	−0.038 (4)	0.021 (4)
C61	0.077 (5)	0.108 (6)	0.086 (5)	−0.069 (4)	−0.054 (4)	0.042 (4)
C62	0.059 (4)	0.089 (5)	0.066 (4)	−0.052 (4)	−0.033 (4)	0.030 (4)
C63	0.034 (3)	0.061 (3)	0.046 (3)	−0.023 (3)	−0.019 (3)	0.016 (3)
C64	0.036 (3)	0.035 (3)	0.052 (3)	−0.015 (2)	−0.018 (3)	0.009 (2)

Geometric parameters (Å, º)

Sb3—I1	3.179 (1)	C28—H28	0.9300
Sb3—I2	3.046 (1)	C29—C30	1.361 (10)
Sb3—I3	2.984 (1)	C29—H29	0.9300
Sb3—I4	2.957 (1)	C30—C31	1.389 (8)
Sb3—I5	2.834 (1)	C30—H30	0.9300
Sb3—I1^i	3.400 (1)	C31—C32	1.467 (8)
Sb4—I6	2.849 (1)	Sb2—N11	2.185 (4)
Sb4—I7	2.814 (1)	Sb2—N13	2.189 (4)
Sb4—I8	2.779 (1)	Sb2—N9	2.212 (4)
Sb4—I2	3.354 (1)	Sb2—N15	2.217 (4)
Sb4—I1^i	3.362 (1)	Sb2—I2	3.5426 (9)
Sb4—I3^i	3.3705 (9)	Sb2—I4	3.548 (1)
Sb1—N1	2.181 (4)	Sb2—I5	3.918 (1)
Sb1—N7	2.189 (4)	N9—C33	1.383 (6)
Sb1—N3	2.191 (4)	N9—C40	1.383 (7)
Sb1—N5	2.209 (4)	N10—C40	1.322 (6)
Sb1—I4	3.653 (1)	N10—C41	1.347 (7)
Sb1—I6	3.729 (1)	N11—C41	1.378 (7)
Sb1—I1^i	3.546 (1)	N11—C48	1.390 (6)
N1—C8	1.383 (7)	N12—C49	1.313 (6)
N1—C1	1.391 (7)	N12—C48	1.326 (7)
N2—C8	1.331 (7)	N13—C49	1.386 (6)
N2—C9	1.344 (6)	N13—C56	1.404 (6)
N3—C9	1.375 (6)	N14—C56	1.323 (6)
N3—C16	1.384 (6)	N14—C57	1.332 (6)
N4—C16	1.325 (6)	N15—C57	1.367 (7)
N4—C17	1.338 (6)	N15—C64	1.374 (6)
N5—C24	1.363 (6)	N16—C33	1.321 (6)
N5—C17	1.376 (6)	N16—C64	1.347 (7)
N6—C24	1.328 (6)	C33—C34	1.441 (7)
N6—C25	1.328 (7)	C34—C39	1.407 (7)
N7—C32	1.379 (7)	C34—C35	1.410 (7)
N7—C25	1.381 (7)	C35—C36	1.377 (8)
N8—C32	1.306 (7)	C35—H35	0.9300
N8—C1	1.313 (7)	C36—C37	1.395 (9)
C1—C2	1.443 (8)	C36—H36	0.9300
C2—C3	1.396 (9)	C37—C38	1.372 (8)
C2—C7	1.413 (9)	C37—H37	0.9300
C3—C4	1.346 (11)	C38—C39	1.405 (7)
C3—H3	0.9300	C38—H38	0.9300
C4—C5	1.403 (12)	C39—C40	1.433 (7)
C4—H4	0.9300	C41—C42	1.445 (7)
C5—C6	1.393 (11)	C42—C43	1.383 (8)
C5—H5	0.9300	C42—C47	1.389 (8)
C6—C7	1.389 (9)	C43—C44	1.392 (8)
C6—H6	0.9300	C43—H43	0.9300
C7—C8	1.440 (8)	C44—C45	1.394 (9)
C9—C10	1.435 (7)	C44—H44	0.9300
C10—C15	1.409 (7)	C45—C46	1.384 (8)
C10—C11	1.424 (7)	C45—H45	0.9300
C11—C12	1.360 (8)	C46—C47	1.420 (7)
C11—H11	0.9300	C46—H46	0.9300
C12—C13	1.394 (8)	C47—C48	1.464 (7)
C12—H12	0.9300	C49—C50	1.452 (7)
C13—C14	1.396 (8)	C50—C55	1.381 (7)
C13—H13	0.9300	C50—C51	1.384 (7)
C14—C15	1.381 (7)	C51—C52	1.369 (8)
C14—H14	0.9300	C51—H51	0.9300
C15—C16	1.460 (7)	C52—C53	1.368 (9)
C17—C18	1.446 (7)	C52—H52	0.9300
C18—C23	1.396 (7)	C53—C54	1.379 (8)
C18—C19	1.400 (8)	C53—H53	0.9300
C19—C20	1.384 (8)	C54—C55	1.399 (8)
C19—H19	0.9300	C54—H54	0.9300
C20—C21	1.358 (10)	C55—C56	1.452 (7)
C20—H20	0.9300	C57—C58	1.464 (7)
C21—C22	1.365 (9)	C58—C59	1.380 (7)
C21—H21	0.9300	C58—C63	1.394 (7)
C22—C23	1.390 (7)	C59—C60	1.390 (8)
C22—H22	0.9300	C59—H59	0.9300
C23—C24	1.446 (7)	C60—C61	1.426 (9)
C25—C26	1.434 (7)	C60—H60	0.9300
C26—C31	1.390 (8)	C61—C62	1.363 (8)
C26—C27	1.392 (8)	C61—H61	0.9300
C27—C28	1.368 (9)	C62—C63	1.399 (7)
C27—H27	0.9300	C62—H62	0.9300
C28—C29	1.405 (11)	C63—C64	1.455 (7)
I1—Sb3—I3	88.53 (4)	C30—C29—C28	121.9 (7)
I1—Sb3—I2	90.36 (4)	C30—C29—H29	119.1
I1—Sb3—I5	95.39 (4)	C28—C29—H29	119.1
I1—Sb3—I4	172.56 (2)	C29—C30—C31	117.3 (7)
I1—Sb3—I1^i	77.15 (4)	C29—C30—H30	121.4
I2—Sb3—I1^i	88.77 (3)	C31—C30—H30	121.4
I2—Sb3—I3	175.08 (2)	C30—C31—C26	121.4 (6)
I2—Sb3—I4	91.79 (4)	C30—C31—C32	131.6 (7)
I2—Sb3—I5	87.81 (3)	C26—C31—C32	107.0 (5)
I3—Sb3—I4	88.73 (4)	N8—C32—N7	129.0 (5)
I3—Sb3—I5	97.06 (3)	N8—C32—C31	122.7 (5)
I4—Sb3—I5	91.81 (4)	N7—C32—C31	108.3 (5)
I6—Sb4—I7	96.70 (4)	N11—Sb2—N13	77.7 (2)
I6—Sb4—I8	91.32 (4)	N11—Sb2—N9	78.0 (2)
I6—Sb4—I1^i	89.12 (4)	N13—Sb2—N9	124.4 (2)
I6—Sb4—I2^i	113.17 (4)	N11—Sb2—N15	126.4 (2)
I6—Sb4—I3^i	168.44 (2)	N13—Sb2—N15	78.3 (2)
I7—Sb4—I8	96.66 (4)	N9—Sb2—N15	77.4 (2)
I7—Sb4—I3^i	94.86 (4)	C33—N9—C40	107.7 (4)
I8—Sb4—I1^i	92.25 (4)	C33—N9—Sb2	122.7 (3)
I8—Sb4—I3^i	87.32 (4)	C40—N9—Sb2	124.4 (3)
Sb3—I2—Sb4	96.53 (3)	C40—N10—C41	121.7 (5)
Sb3—I1—Sb4^i	94.08 (4)	C41—N11—C48	108.3 (4)
Sb3—I3—Sb4^i	97.61 (4)	C41—N11—Sb2	124.4 (3)
N1—Sb1—N7	78.7 (2)	C48—N11—Sb2	123.2 (4)
N1—Sb1—N3	78.0 (2)	C49—N12—C48	122.3 (5)
N7—Sb1—N3	126.6 (2)	C49—N13—C56	107.8 (4)
N1—Sb1—N5	125.0 (2)	C49—N13—Sb2	124.0 (3)
N7—Sb1—N5	77.3 (2)	C56—N13—Sb2	123.9 (3)
N3—Sb1—N5	78.0 (2)	C56—N14—C57	122.2 (5)
C8—N1—C1	109.1 (5)	C57—N15—C64	108.1 (4)
C8—N1—Sb1	122.8 (3)	C57—N15—Sb2	123.4 (3)
C1—N1—Sb1	121.9 (4)	C64—N15—Sb2	121.6 (3)
C8—N2—C9	122.3 (5)	C33—N16—C64	122.3 (4)
C9—N3—C16	107.6 (4)	N16—C33—N9	128.4 (5)
C9—N3—Sb1	123.6 (3)	N16—C33—C34	122.4 (5)
C16—N3—Sb1	121.8 (3)	N9—C33—C34	109.2 (5)
C16—N4—C17	122.1 (4)	C39—C34—C35	119.5 (5)
C24—N5—C17	107.7 (4)	C39—C34—C33	106.7 (5)
C24—N5—Sb1	122.6 (3)	C35—C34—C33	133.8 (5)
C17—N5—Sb1	121.5 (3)	C36—C35—C34	118.3 (6)
C24—N6—C25	122.8 (5)	C36—C35—H35	120.9
C32—N7—C25	108.0 (4)	C34—C35—H35	120.9
C32—N7—Sb1	122.5 (4)	C35—C36—C37	121.4 (6)
C25—N7—Sb1	123.9 (3)	C35—C36—H36	119.3
C32—N8—C1	121.9 (5)	C37—C36—H36	119.3
N8—C1—N1	129.1 (5)	C38—C37—C36	121.9 (6)
N8—C1—C2	123.6 (6)	C38—C37—H37	119.0
N1—C1—C2	107.3 (6)	C36—C37—H37	119.0
C3—C2—C7	120.7 (7)	C37—C38—C39	117.3 (6)
C3—C2—C1	130.8 (7)	C37—C38—H38	121.3
C7—C2—C1	108.5 (5)	C39—C38—H38	121.3
C4—C3—C2	117.3 (8)	C38—C39—C34	121.6 (5)
C4—C3—H3	121.3	C38—C39—C40	131.6 (5)
C2—C3—H3	121.3	C34—C39—C40	106.8 (5)
C3—C4—C5	123.2 (8)	N10—C40—N9	127.9 (5)
C3—C4—H4	118.4	N10—C40—C39	122.5 (5)
C5—C4—H4	118.4	N9—C40—C39	109.6 (4)
C6—C5—C4	120.4 (8)	N10—C41—N11	128.5 (5)
C6—C5—H5	119.8	N10—C41—C42	121.6 (5)
C4—C5—H5	119.8	N11—C41—C42	109.6 (5)
C7—C6—C5	117.1 (8)	C43—C42—C47	120.9 (6)
C7—C6—H6	121.4	C43—C42—C41	132.3 (6)
C5—C6—H6	121.4	C47—C42—C41	106.7 (5)
C6—C7—C2	121.2 (6)	C42—C43—C44	118.6 (6)
C6—C7—C8	132.9 (7)	C42—C43—H43	120.7
C2—C7—C8	105.7 (5)	C44—C43—H43	120.7
N2—C8—N1	127.9 (5)	C45—C44—C43	119.3 (6)
N2—C8—C7	122.6 (6)	C45—C44—H44	120.4
N1—C8—C7	109.4 (5)	C43—C44—H44	120.4
N2—C9—N3	126.8 (5)	C46—C45—C44	124.5 (6)
N2—C9—C10	122.6 (5)	C46—C45—H45	117.7
N3—C9—C10	110.5 (4)	C44—C45—H45	117.7
C15—C10—C11	119.8 (5)	C45—C46—C47	114.4 (6)
C15—C10—C9	106.4 (4)	C45—C46—H46	122.8
C11—C10—C9	133.8 (5)	C47—C46—H46	122.8
C12—C11—C10	117.5 (6)	C42—C47—C46	122.3 (6)
C12—C11—H11	121.3	C42—C47—C48	107.4 (5)
C10—C11—H11	121.3	C46—C47—C48	130.3 (6)
C11—C12—C13	122.6 (5)	N12—C48—N11	127.9 (5)
C11—C12—H12	118.7	N12—C48—C47	124.1 (5)
C13—C12—H12	118.7	N11—C48—C47	107.9 (5)
C12—C13—C14	120.6 (5)	N12—C49—N13	127.3 (5)
C12—C13—H13	119.7	N12—C49—C50	123.4 (4)
C14—C13—H13	119.7	N13—C49—C50	109.1 (5)
C15—C14—C13	118.0 (6)	C55—C50—C51	121.2 (5)
C15—C14—H14	121.0	C55—C50—C49	107.1 (4)
C13—C14—H14	121.0	C51—C50—C49	131.8 (5)
C14—C15—C10	121.5 (5)	C52—C51—C50	117.8 (6)
C14—C15—C16	132.2 (5)	C52—C51—H51	121.1
C10—C15—C16	106.4 (4)	C50—C51—H51	121.1
N4—C16—N3	128.3 (5)	C51—C52—C53	121.3 (6)
N4—C16—C15	122.6 (5)	C51—C52—H52	119.4
N3—C16—C15	109.1 (4)	C53—C52—H52	119.4
N4—C17—N5	128.0 (5)	C52—C53—C54	122.3 (6)
N4—C17—C18	122.6 (4)	C52—C53—H53	118.8
N5—C17—C18	109.4 (4)	C54—C53—H53	118.8
C23—C18—C19	121.8 (5)	C53—C54—C55	116.5 (6)
C23—C18—C17	106.6 (5)	C53—C54—H54	121.7
C19—C18—C17	131.6 (5)	C55—C54—H54	121.7
C20—C19—C18	115.2 (6)	C50—C55—C54	120.9 (5)
C20—C19—H19	122.4	C50—C55—C56	107.9 (5)
C18—C19—H19	122.4	C54—C55—C56	131.1 (5)
C21—C20—C19	123.1 (7)	N14—C56—N13	128.6 (5)
C21—C20—H20	118.5	N14—C56—C55	123.4 (5)
C19—C20—H20	118.5	N13—C56—C55	108.0 (4)
C20—C21—C22	121.9 (6)	N14—C57—N15	128.0 (5)
C20—C21—H21	119.0	N14—C57—C58	122.9 (5)
C22—C21—H21	119.0	N15—C57—C58	109.1 (4)
C21—C22—C23	117.6 (6)	C59—C58—C63	121.2 (5)
C21—C22—H22	121.2	C59—C58—C57	131.9 (5)
C23—C22—H22	121.2	C63—C58—C57	106.9 (5)
C22—C23—C18	120.3 (5)	C58—C59—C60	118.9 (6)
C22—C23—C24	133.5 (5)	C58—C59—H59	120.6
C18—C23—C24	106.2 (4)	C60—C59—H59	120.6
N6—C24—N5	128.2 (5)	C59—C60—C61	119.4 (6)
N6—C24—C23	121.7 (5)	C59—C60—H60	120.3
N5—C24—C23	110.1 (4)	C61—C60—H60	120.3
N6—C25—N7	126.4 (5)	C62—C61—C60	121.5 (6)
N6—C25—C26	123.6 (5)	C62—C61—H61	119.3
N7—C25—C26	109.9 (5)	C60—C61—H61	119.3
C31—C26—C27	120.8 (5)	C61—C62—C63	118.4 (6)
C31—C26—C25	106.8 (5)	C61—C62—H62	120.8
C27—C26—C25	132.4 (6)	C63—C62—H62	120.8
C28—C27—C26	117.7 (7)	C58—C63—C62	120.6 (5)
C28—C27—H27	121.2	C58—C63—C64	105.9 (5)
C26—C27—H27	121.2	C62—C63—C64	133.5 (5)
C27—C28—C29	120.9 (7)	N16—C64—N15	127.1 (5)
C27—C28—H28	119.5	N16—C64—C63	123.0 (5)
C29—C28—H28	119.5	N15—C64—C63	109.9 (5)

Symmetry code: (i) −x+1, −y+1, −z.