Iodo­(phthalocyaninato)­chromium(III)

A new chromium(III)-phthalocyanine complex with the formula [Cr(C₃₂H₁₆N₈)I], or CrPcI where Pc is phthalocyanate(2-), has been obtained by the reaction of pure Cr powder with phthalo­nitrile under a stream of iodine vapour. The five-coordinate Cr atom is bonded to the four iso­indole N atoms of the phthalocyaninate(2-) ligand and to one apical iodine ligand, and has a square-pyramidal coordination geometry. The Cr^III cation is significantly displaced [0.456 (2) Å] from the N₄-iso­indole plane towards the I atom. The Cr-I bond is tilted 2.51 (4)° to the N₄-iso­indole plane.

S1. Comment

This study is a part of our investigation on the synthesis and characterization of metallophthalocyanines obtained under a stream of iodine vapour. Earlier, we reported that in these conditions, usually the crystals of iodine-doped metallophthalocyaninato complexes, in which the iodine-doped atoms form chains of the disordered symmetrical triiodide ions (Janczak et al., 1998, 2000; Janczak, Kubiak & Jezierski et al., 1999a; Janczak & Kubiak, 1999a; Janczak & Idemori, 2001) or ordered but unsymmetrical triiodide ions (Janczak & Kubiak, 1999b; Kubiak et al., 1999) are formed. The iodine atoms can also be directly joined to the central metal ion yielding mono- or diiodometallophthalocyanine complexes (Janczak & Kubiak, 1999c,d) as well as can form a neutral molecule of I₂ which is a bridge for dimerization or for developing a polymeric structure of mono- and diiodometallophtalocyanine complexes (Janczak, Razik & Kubiak et al., 1999). \sch

The crystal of the title compound, (I), is built up from discrete molecules (Fig. 1). The central chromium cation is five-coordinated by four isoindole nitrogen atoms of phthalocyaninato(2-) macrocyclic ligand and one apical iodine atom in a square pyramidal geometry. The chromium cation is significantly displaced [0.456 (2) Å] from the plane defined by four isoindole nitrogen atoms towards the iodine atom. For a comparison, the displacement of the central metal ion in other iodo(phthalocyaninato(2-)metal(III) complexes is equal to 0.258 (2) Å in FePcI (Janczak, Razik & Kubiak et al., 1999), 0.322 (2) Å in VPcI (Ejsmont & Kubiak, 1998), 0.738 (3) Å in InPcI (Janczak & Kubiak, 1999c) and 0.959 (3) Å in TlPcI (Schweiger et al., 1998). In this series of M^IIIPcI complexes the displacement of the metal ion from the N₄-isoindole plane correlate with the M—N_iso distances. However, the effective ionic radius for Cr³⁺ and Fe³⁺ are not different significantly (Shannon, 1976), but the displacement of the Cr atom from the N₄-isoindole plane is significantly greater than the corresponding displacement in FePcI complex, since according to the calculation by Whangbo & Stewart (1983) the 3 d electrons of chromium are more localized at higher in energy than the ring π electrons whereas Fe levels are much closer. This will result in better overlaps of the orbitals and more covalency Fe—N_iso than Cr—N_iso. In both InPcI and TlPcI complexes the displacement of the central metal cation is significantly greater in relation to Cr, Fe and V analogues, since both In³⁺, Tl³⁺ are closed-shell (d¹⁰) ions, and the displacement of In³⁺ and Tl³⁺ from the N₄-isoindole plane correlate well with the effective ionic radius, In³⁺ sim 0.71 Å and Tl³⁺ sim 0.82 Å (Shannon, 1976).

The Cr—I bond length [2.5769 (7) Å] is the shortest M—I bond in this class of M^IIIPcI complexes. The equivalent M—I bond length is equal to 2.628 (1), 2.665 (1), 2.672 (1) and 2,674 (1) in the VPcI, FePcI, InPcI and TlPcI, respectively. The Cr—N_iso bond lengths are slightly longer than those found in the dichloro derivate (Moubaraki et al., 1990), since in CrPcCl₂ the chromium cation lies closely in the centre of one oxidized phthalocyaninato(1-) ring and the chloride atoms are axially joined to the Cr on both sides of the phthalocyaninato(1-) ring.

The bonding interaction of the central chromium cation with apically joined iodine atom leads to the deformation of the phthalocyaninato(2-) macroring in the saucer-shaped form. The greatest deviation from the N₄-isoindole plane is observed for the outermost carbon atoms of the phenyl rings C18—C23 and C26—C31, as a result of the face-to-face orientation and overlapping of the neighbouring CrPcI molecules, which are slightly joined by I···H intermolecular donor-acceptor interaction. This gives pairs of face-to-face but stepped CrPcI molecules in the crystal (Fig.2), and is also the reason for the 2.51 (4)° tilt of the Cr—I bond with respect to the normal to the N₄-isoindole plane. Thus the CrPcI molecule is close to C_s symmetry and not to C_4v, which is expected in the solution. In the face-to-face pairs of CrPcI molecules there are two equivalent I···H intermolecular hydrogen bonds. Both I···H3ⁱ and Iⁱ···H3 distances are equal to 3.109 Å and I···H3ⁱ—C3ⁱ angle [(i) = -x, -y, -z] is equal to 164°. The isoindole moieties of the phthalocyaninato(2-) macroring are almost planar. The dihedral angles between the N₄-isoindole plane and the planes of four isoindole moieties are 4.2 (1), 2.8 (1), 4.1 (1) and 6.6 (1)°, for the N1C1,C8, N3C9,C16, N5C17,C24 and N7C25,C32, respectively.

Although there is no imposed crystallographic symmetry on the phthalocyaninato(2-) macroring, the bond distances and angles for the chemically equivalent bonds do not differ significantly and compare well with the equivalent bond lengths and angles of the other metallophthalocyanines structures.

Related literature

For related literature, see: Ejsmont & Kubiak (1998); Janczak & Idemori (2001); Janczak & Kubiak (1999a, 1999b, 1999c, 1999d); Janczak et al. (1998, 2000); Janczak, Kubiak & Jezierski (1999); Janczak, Razik & Kubiak (1999); Kubiak & Janczak (1993); Moubaraki et al. (1990); Schweiger et al. (1998); Shannon (1976); Whangbo & Stewart (1983).

S2. Experimental

The crystals of CrPcI were obtained by the direct reaction of the pure powdered chromium with 1,2-dicyanobenzene (Kubiak & Janczak, 1993) under a stream of iodine vapours at about 495 K. At this temperature the liquid 1,2-dicyanobenzene undergoes catalytic tetramerization with simultaneous transfer of two electrons from Cr metal to the forming of Pc ring, the third electron from Cr is transfered to the iodine atom to form a I^- ion.

Computing details

Data collection: KUMA KM-4 CCD software (Kuma, 2000); cell refinement: KUMA KM-4 CCD software; data reduction: KUMA KM-4 CCD software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure showing 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Molecular packing in the unit cell showing the pseudo-dimers of the CrPcI molecules.

(I)

Crystal data

[CrI(C32H16N8)]	F(000) = 1364
Mr = 691.43	Dx = 1.746 Mg m^−3 Dm = 1.74 Mg m^−3 Dm measured by flotation
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.173 (3) Å	Cell parameters from 458 reflections
b = 10.424 (2) Å	θ = 5–25°
c = 19.435 (4) Å	µ = 1.65 mm^−1
β = 99.76 (3)°	T = 293 K
V = 2630.1 (10) Å^3	Parallelepiped, black-violet
Z = 4	0.16 × 0.12 × 0.10 mm

Data collection

KUMA KM-4 with area CCD detector diffractometer	6441 independent reflections
Radiation source: fine-focus sealed tube	3350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	θmax = 28.5°, θmin = 3.5°
ω–scan	h = −13→17
Absorption correction: analytical face-indexed (SHELXTL; Sheldrick, 1990)	k = −13→13
Tmin = 0.778, Tmax = 0.852	l = −25→25
22036 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0088P)^2] where P = (Fo^2 + 2Fc^2)/3
6441 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. 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 97% 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.

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
I	0.242322 (17)	0.21882 (2)	0.128705 (12)	0.05706 (8)
Cr	0.31742 (4)	0.04779 (4)	0.05580 (3)	0.04495 (15)
N1	0.22425 (18)	0.0610 (2)	−0.03695 (12)	0.0403 (6)
N2	0.3069 (2)	0.2378 (2)	−0.08731 (12)	0.0395 (6)
N3	0.41992 (19)	0.1538 (2)	0.01498 (13)	0.0399 (6)
N4	0.57460 (18)	0.1239 (2)	0.10113 (14)	0.0416 (6)
N5	0.43908 (18)	−0.0243 (2)	0.12028 (12)	0.0392 (6)
N6	0.3552 (2)	−0.2007 (2)	0.17109 (13)	0.0452 (7)
N7	0.2412 (2)	−0.1149 (2)	0.07079 (13)	0.0427 (7)
N8	0.09697 (18)	−0.1039 (2)	−0.02391 (14)	0.0427 (6)
C1	0.1326 (2)	−0.0043 (3)	−0.05579 (17)	0.0409 (8)
C2	0.0767 (3)	0.0510 (3)	−0.11968 (18)	0.0421 (8)
C3	−0.0178 (3)	0.0228 (3)	−0.16044 (19)	0.0510 (9)
H3	−0.0581	−0.0445	−0.1489	0.061*
C4	−0.0499 (3)	0.0971 (4)	−0.21802 (19)	0.0558 (9)
H4	−0.1129	0.0799	−0.2461	0.067*
C5	0.0095 (3)	0.1970 (4)	−0.23508 (18)	0.0594 (10)
H5	−0.0151	0.2457	−0.2745	0.071*
C6	0.1036 (3)	0.2279 (3)	−0.19640 (18)	0.0533 (9)
H6	0.1430	0.2954	−0.2088	0.064*
C7	0.1366 (2)	0.1534 (3)	−0.13800 (17)	0.0426 (8)
C8	0.2297 (3)	0.1570 (3)	−0.08552 (16)	0.0401 (8)
C9	0.3948 (2)	0.2331 (3)	−0.04200 (17)	0.0382 (8)
C10	0.4820 (2)	0.3184 (3)	−0.04798 (17)	0.0408 (8)
C11	0.4945 (3)	0.4153 (3)	−0.09425 (17)	0.0482 (9)
H11	0.4425	0.4359	−0.1312	0.058*
C12	0.5870 (3)	0.4805 (3)	−0.08348 (19)	0.0539 (9)
H12	0.5974	0.5470	−0.1134	0.065*
C13	0.6652 (3)	0.4482 (3)	−0.0285 (2)	0.0571 (10)
H13	0.7263	0.4947	−0.0223	0.068*
C14	0.6544 (2)	0.3490 (3)	0.01720 (17)	0.0478 (9)
H14	0.7076	0.3268	0.0531	0.057*
C15	0.5603 (2)	0.2834 (3)	0.00717 (16)	0.0415 (8)
C16	0.5211 (2)	0.1808 (3)	0.04607 (18)	0.0411 (8)
C17	0.5366 (3)	0.0288 (3)	0.13446 (17)	0.0433 (8)
C18	0.5957 (3)	−0.0365 (3)	0.19499 (17)	0.0444 (8)
C19	0.6964 (3)	−0.0220 (3)	0.23204 (19)	0.0547 (9)
H19	0.7404	0.0406	0.2198	0.066*
C20	0.7274 (3)	−0.1041 (4)	0.28712 (19)	0.0667 (10)
H20	0.7934	−0.0961	0.3128	0.080*
C21	0.6623 (3)	−0.1988 (4)	0.30524 (19)	0.0667 (10)
H21	0.6865	−0.2529	0.3424	0.080*
C22	0.5646 (3)	−0.2148 (3)	0.27044 (18)	0.0564 (9)
H22	0.5216	−0.2781	0.2831	0.068*
C23	0.5322 (3)	−0.1323 (3)	0.21519 (17)	0.0444 (8)
C24	0.4338 (3)	−0.1219 (3)	0.16765 (17)	0.0417 (8)
C25	0.2688 (3)	−0.1981 (3)	0.12615 (18)	0.0449 (8)
C26	0.1877 (3)	−0.2953 (3)	0.12443 (18)	0.0463 (8)
C27	0.1790 (3)	−0.3995 (3)	0.16736 (18)	0.0552 (9)
H27	0.2296	−0.4181	0.2056	0.066*
C28	0.0922 (3)	−0.4740 (3)	0.1508 (2)	0.0641 (11)
H28	0.0845	−0.5453	0.1782	0.077*
C29	0.0162 (3)	−0.4459 (3)	0.0948 (2)	0.0687 (12)
H29	−0.0420	−0.4979	0.0859	0.082*
C30	0.0243 (3)	−0.3413 (3)	0.05101 (18)	0.0572 (10)
H30	−0.0266	−0.3225	0.0131	0.069*
C31	0.1130 (3)	−0.2670 (3)	0.06740 (17)	0.0439 (8)
C32	0.1479 (3)	−0.1539 (3)	0.03389 (18)	0.0411 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.05315 (14)	0.05075 (13)	0.06958 (16)	−0.00677 (14)	0.01698 (11)	−0.01334 (14)
Cr	0.0431 (3)	0.0424 (3)	0.0497 (3)	−0.0010 (3)	0.0089 (3)	−0.0016 (3)
N1	0.0400 (16)	0.0396 (16)	0.0416 (17)	−0.0073 (13)	0.0075 (14)	−0.0036 (13)
N2	0.0400 (16)	0.0420 (17)	0.0373 (15)	−0.0084 (13)	0.0094 (14)	−0.0006 (13)
N3	0.0362 (17)	0.0444 (16)	0.0397 (17)	−0.0033 (13)	0.0083 (14)	−0.0024 (13)
N4	0.0394 (17)	0.0442 (17)	0.0411 (17)	0.0028 (14)	0.0065 (14)	−0.0044 (14)
N5	0.0368 (17)	0.0388 (16)	0.0412 (16)	−0.0010 (13)	0.0045 (14)	−0.0007 (14)
N6	0.0540 (19)	0.0354 (16)	0.0487 (18)	−0.0013 (16)	0.0159 (16)	−0.0015 (14)
N7	0.0506 (18)	0.0360 (15)	0.0425 (18)	0.0015 (14)	0.0109 (15)	−0.0026 (14)
N8	0.0406 (17)	0.0470 (17)	0.0429 (18)	−0.0058 (14)	0.0139 (15)	−0.0070 (15)
C1	0.038 (2)	0.047 (2)	0.039 (2)	−0.0008 (18)	0.0127 (18)	−0.0123 (18)
C2	0.036 (2)	0.043 (2)	0.048 (2)	−0.0009 (17)	0.0108 (19)	−0.0124 (18)
C3	0.040 (2)	0.054 (2)	0.059 (2)	−0.0031 (18)	0.010 (2)	−0.008 (2)
C4	0.043 (2)	0.071 (3)	0.051 (2)	−0.005 (2)	−0.0021 (19)	−0.009 (2)
C5	0.053 (2)	0.070 (3)	0.053 (2)	0.004 (2)	0.003 (2)	0.002 (2)
C6	0.047 (2)	0.053 (2)	0.061 (2)	−0.008 (2)	0.013 (2)	0.004 (2)
C7	0.039 (2)	0.047 (2)	0.041 (2)	0.0003 (17)	0.0043 (18)	−0.0012 (18)
C8	0.046 (2)	0.039 (2)	0.037 (2)	0.0023 (17)	0.0123 (18)	−0.0021 (16)
C9	0.0302 (19)	0.042 (2)	0.043 (2)	−0.0047 (17)	0.0090 (17)	−0.0091 (17)
C10	0.047 (2)	0.035 (2)	0.043 (2)	−0.0041 (16)	0.0133 (19)	−0.0121 (16)
C11	0.050 (2)	0.050 (2)	0.046 (2)	−0.0033 (19)	0.0111 (18)	−0.0033 (18)
C12	0.056 (3)	0.048 (2)	0.061 (3)	−0.014 (2)	0.019 (2)	−0.005 (2)
C13	0.045 (2)	0.054 (2)	0.077 (3)	−0.0092 (19)	0.024 (2)	−0.022 (2)
C14	0.035 (2)	0.055 (2)	0.055 (2)	−0.0098 (17)	0.0148 (18)	−0.0139 (19)
C15	0.047 (2)	0.0398 (18)	0.043 (2)	−0.0004 (19)	0.0222 (18)	−0.0114 (18)
C16	0.035 (2)	0.043 (2)	0.047 (2)	0.0001 (16)	0.0136 (18)	−0.0073 (17)
C17	0.042 (2)	0.044 (2)	0.044 (2)	0.0085 (18)	0.0090 (19)	−0.0051 (18)
C18	0.040 (2)	0.046 (2)	0.046 (2)	0.0084 (18)	0.0051 (19)	−0.0160 (18)
C19	0.051 (3)	0.051 (2)	0.060 (3)	0.0006 (19)	0.006 (2)	−0.012 (2)
C20	0.059 (3)	0.080 (3)	0.053 (3)	0.019 (2)	−0.012 (2)	−0.007 (2)
C21	0.077 (3)	0.051 (2)	0.066 (3)	0.011 (2)	−0.008 (2)	0.004 (2)
C22	0.064 (3)	0.043 (2)	0.059 (2)	0.006 (2)	0.003 (2)	−0.001 (2)
C23	0.052 (2)	0.033 (2)	0.047 (2)	0.0143 (18)	0.006 (2)	−0.0030 (17)
C24	0.052 (2)	0.035 (2)	0.040 (2)	0.0066 (18)	0.0120 (19)	−0.0075 (17)
C25	0.046 (2)	0.045 (2)	0.044 (2)	0.0017 (18)	0.0100 (19)	−0.008 (2)
C26	0.054 (2)	0.037 (2)	0.055 (2)	−0.0092 (19)	0.030 (2)	−0.0090 (19)
C27	0.067 (3)	0.045 (2)	0.057 (2)	0.001 (2)	0.023 (2)	0.0040 (19)
C28	0.091 (3)	0.040 (2)	0.069 (3)	−0.011 (2)	0.038 (3)	0.001 (2)
C29	0.076 (3)	0.043 (2)	0.097 (3)	−0.017 (2)	0.043 (3)	−0.002 (2)
C30	0.056 (2)	0.053 (2)	0.067 (3)	−0.008 (2)	0.022 (2)	0.000 (2)
C31	0.043 (2)	0.043 (2)	0.049 (2)	0.0000 (18)	0.0166 (19)	−0.0047 (19)
C32	0.041 (2)	0.040 (2)	0.043 (2)	−0.0021 (17)	0.0096 (19)	−0.0063 (18)

Geometric parameters (Å, º)

I—Cr	2.5769 (7)	C6—C7	1.383 (4)
Cr—N5	2.006 (2)	C7—C8	1.457 (4)
Cr—N1	2.006 (3)	C9—C10	1.474 (4)
Cr—N3	2.009 (2)	C10—C11	1.381 (4)
Cr—N7	2.016 (2)	C10—C15	1.404 (4)
N1—C1	1.380 (3)	C11—C12	1.380 (4)
N1—C8	1.386 (3)	C12—C13	1.394 (4)
N2—C8	1.326 (3)	C13—C14	1.386 (4)
N2—C9	1.331 (3)	C14—C15	1.400 (4)
N3—C9	1.377 (3)	C15—C16	1.455 (4)
N3—C16	1.395 (4)	C17—C18	1.464 (4)
N4—C16	1.318 (4)	C18—C23	1.401 (4)
N4—C17	1.328 (4)	C18—C19	1.406 (4)
N5—C24	1.382 (4)	C19—C20	1.377 (4)
N5—C17	1.383 (3)	C20—C21	1.391 (4)
N6—C25	1.312 (4)	C21—C22	1.359 (4)
N6—C24	1.332 (4)	C22—C23	1.386 (4)
N7—C32	1.376 (4)	C23—C24	1.462 (4)
N7—C25	1.382 (4)	C25—C26	1.468 (4)
N8—C32	1.315 (4)	C26—C31	1.384 (4)
N8—C1	1.334 (4)	C26—C27	1.386 (4)
C1—C2	1.451 (4)	C27—C28	1.374 (4)
C2—C3	1.389 (4)	C28—C29	1.381 (5)
C2—C7	1.409 (4)	C29—C30	1.398 (4)
C3—C4	1.368 (4)	C30—C31	1.393 (4)
C4—C5	1.376 (4)	C31—C32	1.458 (4)
C5—C6	1.374 (4)
N5—Cr—N1	152.81 (9)	C11—C10—C15	122.3 (3)
N5—Cr—N3	86.19 (11)	C11—C10—C9	132.3 (3)
N1—Cr—N3	87.55 (10)	C15—C10—C9	105.4 (3)
N5—Cr—N7	87.66 (11)	C12—C11—C10	117.4 (3)
N1—Cr—N7	86.78 (10)	C11—C12—C13	121.1 (3)
N3—Cr—N7	154.66 (9)	C14—C13—C12	121.9 (3)
N5—Cr—I	104.84 (7)	C13—C14—C15	117.3 (3)
N1—Cr—I	102.31 (7)	C14—C15—C10	119.9 (3)
N3—Cr—I	100.54 (7)	C14—C15—C16	132.1 (3)
N7—Cr—I	104.80 (7)	C10—C15—C16	108.0 (3)
C1—N1—C8	108.7 (3)	N4—C16—N3	126.9 (3)
C1—N1—Cr	125.4 (2)	N4—C16—C15	124.4 (3)
C8—N1—Cr	124.5 (2)	N3—C16—C15	108.7 (3)
C8—N2—C9	122.9 (3)	N4—C17—N5	128.0 (3)
C9—N3—C16	108.0 (2)	N4—C17—C18	123.1 (3)
C9—N3—Cr	124.2 (2)	N5—C17—C18	108.9 (3)
C16—N3—Cr	126.6 (2)	C23—C18—C19	119.3 (3)
C16—N4—C17	122.5 (3)	C23—C18—C17	107.2 (3)
C24—N5—C17	108.2 (3)	C19—C18—C17	133.5 (3)
C24—N5—Cr	124.6 (2)	C20—C19—C18	117.4 (4)
C17—N5—Cr	126.2 (2)	C19—C20—C21	121.6 (4)
C25—N6—C24	123.2 (3)	C22—C21—C20	122.2 (4)
C32—N7—C25	108.3 (3)	C21—C22—C23	116.8 (4)
C32—N7—Cr	126.6 (2)	C22—C23—C18	122.6 (3)
C25—N7—Cr	124.7 (2)	C22—C23—C24	131.3 (3)
C32—N8—C1	122.5 (3)	C18—C23—C24	106.1 (3)
N8—C1—N1	128.4 (3)	N6—C24—N5	127.9 (3)
N8—C1—C2	122.6 (3)	N6—C24—C23	122.4 (3)
N1—C1—C2	109.0 (3)	N5—C24—C23	109.6 (3)
C3—C2—C7	120.1 (3)	N6—C25—N7	128.0 (3)
C3—C2—C1	132.8 (3)	N6—C25—C26	123.1 (3)
C7—C2—C1	107.0 (3)	N7—C25—C26	108.7 (3)
C4—C3—C2	118.0 (3)	C31—C26—C27	121.9 (3)
C3—C4—C5	121.1 (3)	C31—C26—C25	106.7 (3)
C6—C5—C4	122.8 (3)	C27—C26—C25	131.4 (4)
C5—C6—C7	116.5 (3)	C28—C27—C26	116.9 (3)
C6—C7—C2	121.4 (3)	C27—C28—C29	121.9 (4)
C6—C7—C8	132.1 (3)	C28—C29—C30	121.7 (4)
C2—C7—C8	106.5 (3)	C31—C30—C29	116.3 (4)
N2—C8—N1	127.3 (3)	C26—C31—C30	121.3 (3)
N2—C8—C7	123.8 (3)	C26—C31—C32	107.1 (3)
N1—C8—C7	108.9 (3)	C30—C31—C32	131.5 (3)
N2—C9—N3	128.2 (3)	N8—C32—N7	127.5 (3)
N2—C9—C10	121.9 (3)	N8—C32—C31	123.3 (3)
N3—C9—C10	109.9 (3)	N7—C32—C31	109.1 (3)