Dibromo[5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato-κ⁴N]platinum(IV) chloroform acetonitrile solvate

In the title compound, [PtBr₂(C₄₈H₃₆N₄O₄)]·0.896CHCl₃·0.569CH₃CN, the centrosymmetric metal complex is octahedral, with the porphyrin ring essentially planar and the Br atoms occupying axial positions. The two independent methoxy­phenyl substituents are tilted at angles of 89.0 and 67.0° with respect to the porphyrin plane. The Pt—N distances are 2.035 (4) and 2.036 (4) Å and the Pt—Br distance is 2.4666 (6) Å. Chloro­form and aceto­nitrile solvent mol­ecules, exhibiting substantial disorder, occupy positions between the porphyrin mol­ecules. This is the first crystal and molecular structure of a Pt^IV–porphyrin complex to be reported.

S1. Comment

Metalloporphyrin reactivity is found to be dependent upon the central metal, the substituents on the porphyrin ring and the axially coordinated ligands (Dolphin, 1978). Platinum porphyrins have been investigated as oxygen-sensing probes (Gouin & Gouterman, 2000), phosphorescent probes in bioanalytical applications (Papkovsky et al., 2000), photosensitizers (Kunkely & Vogler, 1997), potential antitumour agents (Brunner et al., 1997) and molecular conductors (Hiroyuki et al., 2000). Most of the recent studies have focused on Pt^II porphyrins, with relatively few studies pertaining to Pt^IV porphyrin systems. Here, we report the first crystal structure of a Pt^IV porphyrin compound, the title compound, (I). \sch

Complex (I) (Fig. 1) crystallizes in the centrosymmetric space group P2/n, with the Pt atom located at a centre of inversion. The structure of the molecule is typical of many porphyrin complexes. The porphyrin moiety is essentially planar, while the bond lengths and angles within the macrocycle are unremarkable. The p-methoxyphenyl groups are rotated 89 and 67° degrees from the porphyrin mean plane, due to steric hindrance with the meso-H atoms of the macrocycle. Strict coplanarity of the Pt atom and the four pyrrole N atoms is imposed by the inversion centre. The Pt—N bond lengths (Table 1) are longer than those found in Pt^II analogues. For example, the Pt^II—N distances in tetraphenylporphinatoplatinum(II), (Hazell, 1984) and the analogous 2,3,7,8,12,13,17,18-octaethylporphinatoplatinum(II) (Milgrom et al., 1988), are found to be 2.008 and 2.012 (3) Å, respectively. The Pt^II—N_porphyrin bonds are considered to be shorter then typical Pt^II—N complex bonds, due to extensive metal d(π)-porphyrin π* overlap (Milgrom et al., 1988). The longer Pt^IV—N bonds observed in (I) are attributed to a decrease in metal d(π)-porphyrin π* bonding upon oxidation of Pt^II to Pt^IV, as evident in the electronic spectrum of the compound (Mink et al., 1997; Mink et al., 2000).

The molecules of (I) pack with the porphyrinato moieties forming face-centred parallel layers along the ac face of the unit cell. Within each layer, the porphyrinato moieties at the corners of the unit cell lie parallel to each other, each making angles of 29.6 and 19.5° to the b and c edges, respectively (measured in the ac and bc planes). The moiety at the centre of the face makes the same angles to the b and c edges but in the opposite direction. The overall effect is to produce a layer with a herring-bone pattern when viewed from the side (Fig. 2).

Solvent molecules are packed between the porphyrin layers. A chloroform molecule is found on a twofold axis, while another solvent site is shared between chloroform and acetonitrile molecules. The solvent molecules appear to be within van der Waals contact distances to the porphyrins, suggesting that it is the solvent that holds the crystal together. This is borne out by the rapid deterioration of the crystals when they are removed from the solvent and allowed to desolvate; the crystals become very brittle and crumble easily.

S2. Experimental

Compound (I) was synthesized by direct oxidation of the Pt^II analogue with bromine, according to methods reported previously by Mink et al. (2000).

S3. Refinement

H atoms were treated as riding, with C—H distances in the range 0.93–0.98 Å. Is this added text correct?

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996; data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii and the solvent molecules have been omitted for clarity.
	Fig. 2. A view of (I) down the (001) face, showing the herring-bone packing arrangement of the porphyrin molecules. H atoms and solvent molecules have been omitted for clarity.

Dibromo[5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato-κ⁴N]platinum(IV) chloroform/acetonitrile solvate

Crystal data

[Pt(C48H36N4O4)Br2]·(CHCl3)0.896·(C2H3N)0.569	F(000) = 1322
Mr = 1348.32	Dx = 1.728 Mg m^−3
Monoclinic, P2/n	Melting point: 305 K
Hall symbol: -P 2yac	Mo Kα radiation, λ = 0.71073 Å
a = 14.8727 (7) Å	Cell parameters from 6264 reflections
b = 9.4421 (5) Å	θ = 9.5–28.3°
c = 18.5973 (9) Å	µ = 4.60 mm^−1
β = 99.348 (1)°	T = 294 K
V = 2576.9 (2) Å^3	Elongated prism, purple
Z = 2	0.30 × 0.15 × 0.10 mm

Data collection

Siemens SMART P3/512 CCD area-detector diffractometer	5931 independent reflections
Radiation source: fine-focus sealed tube	4440 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −19→19
Tmin = 0.517, Tmax = 0.629	k = −11→12
25609 measured reflections	l = −23→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.82	(Δ/σ)max = 0.033
5931 reflections	Δρmax = 0.61 e Å^−3
371 parameters	Δρmin = −0.80 e Å^−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (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	Occ. (<1)
Pt1	0.0000	0.0000	0.0000	0.02325 (11)
Br1	0.09115 (4)	−0.20927 (6)	0.04548 (3)	0.03804 (16)
N1	−0.1013 (3)	−0.0710 (5)	0.0524 (2)	0.0256 (9)
C1	−0.1714 (3)	−0.1601 (6)	0.0245 (3)	0.0282 (11)
N2	0.0555 (3)	0.1091 (5)	0.0908 (2)	0.0269 (9)
C2	−0.2245 (4)	−0.1895 (6)	0.0801 (3)	0.0330 (12)
H2A	−0.2763	−0.2461	0.0753	0.040*
C3	−0.1864 (4)	−0.1209 (7)	0.1407 (3)	0.0380 (14)
H3A	−0.2071	−0.1216	0.1853	0.046*
C4	−0.1081 (4)	−0.0465 (6)	0.1244 (3)	0.0294 (12)
C5	−0.0499 (4)	0.0345 (6)	0.1735 (3)	0.0319 (13)
C6	0.0253 (4)	0.1077 (6)	0.1571 (3)	0.0279 (11)
C7	0.0854 (4)	0.1935 (6)	0.2076 (3)	0.0319 (12)
H7A	0.0803	0.2110	0.2560	0.038*
C8	0.1504 (4)	0.2439 (6)	0.1720 (3)	0.0325 (12)
H8A	0.1983	0.3029	0.1914	0.039*
C9	0.1329 (4)	0.1911 (5)	0.0990 (3)	0.0269 (11)
C10	0.1873 (3)	0.2163 (6)	0.0455 (3)	0.0256 (10)
C11	−0.0683 (4)	0.0427 (6)	0.2505 (3)	0.0305 (12)
C12	−0.0311 (4)	−0.0588 (7)	0.3021 (3)	0.0387 (14)
H12A	0.0057	−0.1305	0.2886	0.046*
C13	−0.0488 (4)	−0.0530 (7)	0.3723 (3)	0.0383 (14)
H13A	−0.0233	−0.1203	0.4061	0.046*
C14	−0.1040 (4)	0.0518 (6)	0.3933 (3)	0.0318 (12)
C15	−0.1417 (4)	0.1515 (6)	0.3428 (3)	0.0392 (14)
H15A	−0.1792	0.2224	0.3561	0.047*
C16	−0.1233 (4)	0.1448 (6)	0.2725 (3)	0.0355 (13)
H16A	−0.1492	0.2120	0.2389	0.043*
C17	0.2682 (3)	0.3129 (5)	0.0651 (3)	0.0259 (11)
C18	0.2547 (4)	0.4561 (6)	0.0795 (3)	0.0302 (12)
H18A	0.1959	0.4909	0.0775	0.036*
C19	0.3284 (4)	0.5461 (6)	0.0967 (3)	0.0371 (13)
H19A	0.3188	0.6411	0.1062	0.044*
C20	0.4156 (4)	0.4962 (6)	0.0999 (4)	0.0392 (14)
C21	0.4305 (4)	0.3540 (7)	0.0856 (3)	0.0416 (14)
H21A	0.4895	0.3201	0.0872	0.050*
C22	0.3565 (4)	0.2629 (6)	0.0690 (3)	0.0337 (12)
H22A	0.3664	0.1676	0.0604	0.040*
O23	−0.1162 (3)	0.0486 (5)	0.4645 (2)	0.0441 (10)
C23	−0.1799 (6)	0.1470 (8)	0.4857 (3)	0.063 (2)
H23A	−0.1827	0.1350	0.5365	0.094*
H23B	−0.2390	0.1303	0.4576	0.094*
H23C	−0.1607	0.2417	0.4772	0.094*
O24	0.4836 (3)	0.5944 (5)	0.1161 (3)	0.0650 (15)
C24	0.5749 (5)	0.5470 (9)	0.1230 (6)	0.082 (3)
H24A	0.6154	0.6260	0.1342	0.123*
H24B	0.5848	0.5046	0.0780	0.123*
H24C	0.5864	0.4784	0.1615	0.123*
C100	0.2039 (6)	−0.1401 (7)	0.2274 (5)	0.043 (3)	0.465 (4)
H10A	0.1462	−0.1109	0.1979	0.051*	0.465 (4)
Cl11	0.2034 (4)	−0.3257 (5)	0.2327 (3)	0.095 (2)	0.465 (4)
Cl12	0.2060 (9)	−0.0718 (16)	0.3155 (5)	0.142 (6)	0.465 (4)
Cl13	0.2922 (4)	−0.0735 (6)	0.18561 (19)	0.0377 (13)	0.465 (4)
C200	0.0741 (4)	−0.5661 (10)	−0.1522 (4)	0.058 (6)	0.431 (5)
H20A	0.0823	−0.6594	−0.1291	0.070*	0.431 (5)
Cl14	−0.0259 (4)	−0.5668 (6)	−0.2180 (2)	0.0769 (19)	0.431 (5)
Cl15	0.0617 (4)	−0.4373 (6)	−0.0858 (2)	0.0714 (19)	0.431 (5)
Cl16	0.1691 (5)	−0.5271 (6)	−0.1949 (3)	0.083 (2)	0.431 (5)
N300	0.2056 (10)	−0.4336 (16)	−0.1420 (10)	0.098 (5)	0.569 (5)
C400	0.1390 (12)	−0.4671 (16)	−0.1295 (11)	0.078 (6)	0.569 (5)
C300	0.0550 (11)	−0.5115 (16)	−0.1149 (17)	0.104 (9)	0.569 (5)
H30A	0.0306	−0.5821	−0.1498	0.156*	0.569 (5)
H30B	0.0142	−0.4321	−0.1181	0.156*	0.569 (5)
H30C	0.0621	−0.5509	−0.0668	0.156*	0.569 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.02404 (16)	0.03014 (17)	0.01495 (14)	−0.00686 (12)	0.00131 (10)	0.00219 (11)
Br1	0.0384 (3)	0.0381 (3)	0.0350 (3)	−0.0007 (3)	−0.0019 (2)	0.0091 (3)
N1	0.025 (2)	0.035 (2)	0.018 (2)	−0.0059 (19)	0.0062 (17)	0.0041 (18)
C1	0.029 (3)	0.034 (3)	0.021 (2)	−0.007 (2)	0.000 (2)	0.005 (2)
N2	0.025 (2)	0.039 (3)	0.0164 (19)	−0.0073 (19)	0.0036 (17)	0.0015 (18)
C2	0.030 (3)	0.046 (3)	0.024 (3)	−0.008 (2)	0.008 (2)	0.002 (2)
C3	0.038 (3)	0.055 (4)	0.023 (3)	−0.018 (3)	0.011 (2)	0.000 (3)
C4	0.034 (3)	0.034 (3)	0.019 (2)	−0.009 (2)	0.002 (2)	0.000 (2)
C5	0.032 (3)	0.044 (3)	0.019 (2)	−0.007 (2)	0.000 (2)	0.001 (2)
C6	0.033 (3)	0.031 (3)	0.020 (2)	−0.005 (2)	0.004 (2)	0.000 (2)
C7	0.035 (3)	0.044 (3)	0.016 (2)	−0.009 (2)	0.001 (2)	−0.001 (2)
C8	0.035 (3)	0.037 (3)	0.023 (3)	−0.009 (2)	−0.003 (2)	0.000 (2)
C9	0.035 (3)	0.026 (3)	0.018 (2)	−0.004 (2)	0.000 (2)	0.001 (2)
C10	0.025 (3)	0.030 (3)	0.020 (2)	−0.002 (2)	0.001 (2)	0.001 (2)
C11	0.031 (3)	0.044 (3)	0.016 (2)	−0.010 (2)	0.004 (2)	−0.002 (2)
C12	0.040 (3)	0.051 (3)	0.027 (3)	0.009 (3)	0.011 (3)	0.005 (3)
C13	0.037 (3)	0.050 (3)	0.027 (3)	0.005 (3)	0.006 (3)	0.010 (3)
C14	0.042 (3)	0.039 (3)	0.014 (2)	−0.013 (3)	0.005 (2)	−0.004 (2)
C15	0.055 (4)	0.036 (3)	0.028 (3)	0.000 (3)	0.011 (3)	−0.003 (2)
C16	0.048 (3)	0.034 (3)	0.025 (3)	−0.004 (3)	0.008 (2)	0.003 (2)
C17	0.025 (3)	0.031 (3)	0.022 (2)	−0.009 (2)	0.004 (2)	0.001 (2)
C18	0.029 (3)	0.029 (3)	0.033 (3)	0.001 (2)	0.006 (2)	0.003 (2)
C19	0.039 (3)	0.028 (3)	0.045 (3)	−0.004 (2)	0.009 (3)	0.001 (3)
C20	0.032 (3)	0.035 (3)	0.050 (4)	−0.012 (3)	0.003 (3)	−0.002 (3)
C21	0.024 (3)	0.042 (3)	0.057 (4)	−0.004 (3)	0.000 (3)	−0.006 (3)
C22	0.036 (3)	0.023 (3)	0.041 (3)	−0.003 (2)	0.002 (3)	−0.003 (2)
O23	0.060 (3)	0.052 (2)	0.022 (2)	−0.004 (2)	0.0124 (19)	−0.0013 (19)
C23	0.104 (6)	0.057 (4)	0.034 (3)	0.013 (4)	0.036 (4)	−0.003 (3)
O24	0.043 (3)	0.041 (3)	0.110 (4)	−0.023 (2)	0.010 (3)	−0.014 (3)
C24	0.040 (4)	0.066 (5)	0.140 (9)	−0.024 (4)	0.012 (5)	−0.019 (6)
C100	0.066 (9)	0.044 (7)	0.019 (6)	−0.003 (6)	0.011 (6)	0.004 (5)
Cl11	0.181 (7)	0.055 (3)	0.056 (3)	−0.012 (3)	0.039 (3)	0.001 (2)
Cl12	0.134 (12)	0.160 (12)	0.136 (10)	0.009 (9)	0.035 (8)	0.043 (9)
Cl13	0.049 (3)	0.054 (3)	0.0142 (17)	−0.021 (3)	0.0168 (19)	−0.0031 (19)
C200	0.096 (15)	0.026 (9)	0.054 (10)	0.043 (9)	0.015 (10)	−0.001 (7)
Cl14	0.115 (5)	0.068 (3)	0.040 (2)	0.015 (3)	−0.009 (2)	−0.017 (2)
Cl15	0.111 (5)	0.051 (3)	0.045 (2)	0.031 (3)	−0.008 (2)	−0.007 (2)
Cl16	0.111 (5)	0.059 (3)	0.083 (4)	0.020 (3)	0.031 (4)	0.025 (3)
N300	0.074 (10)	0.061 (9)	0.155 (16)	0.001 (8)	0.009 (10)	0.039 (10)
C400	0.064 (10)	0.051 (9)	0.111 (15)	−0.026 (8)	−0.006 (10)	0.036 (9)
C300	0.056 (10)	0.038 (10)	0.22 (3)	0.022 (8)	0.031 (14)	0.027 (13)

Geometric parameters (Å, º)

Pt1—N2^i	2.035 (4)	C15—C16	1.379 (8)
Pt1—N2	2.035 (4)	C15—H15A	0.9300
Pt1—N1^i	2.036 (4)	C16—H16A	0.9300
Pt1—N1	2.036 (4)	C17—C22	1.385 (7)
Pt1—Br1	2.4668 (6)	C17—C18	1.400 (7)
Pt1—Br1^i	2.4668 (6)	C18—C19	1.383 (8)
N1—C1	1.374 (6)	C18—H18A	0.9300
N1—C4	1.378 (6)	C19—C20	1.372 (9)
C1—C10^i	1.390 (7)	C19—H19A	0.9300
C1—C2	1.428 (7)	C20—O24	1.369 (7)
N2—C9	1.376 (6)	C20—C21	1.394 (8)
N2—C6	1.379 (6)	C21—C22	1.391 (8)
C2—C3	1.342 (7)	C21—H21A	0.9300
C2—H2A	0.9300	C22—H22A	0.9300
C3—C4	1.435 (7)	O23—C23	1.427 (8)
C3—H3A	0.9300	C23—H23A	0.9600
C4—C5	1.383 (8)	C23—H23B	0.9600
C5—C6	1.390 (7)	C23—H23C	0.9600
C5—C11	1.503 (7)	O24—C24	1.415 (9)
C6—C7	1.437 (7)	C24—H24A	0.9600
C7—C8	1.344 (7)	C24—H24B	0.9600
C7—H7A	0.9300	C24—H24C	0.9600
C8—C9	1.429 (7)	C100—Cl13	1.748 (5)
C8—H8A	0.9300	C100—Cl12	1.755 (5)
C9—C10	1.399 (7)	C100—Cl11	1.755 (5)
C10—C1^i	1.390 (7)	C100—H10A	0.9800
C10—C17	1.508 (7)	C200—Cl14	1.765 (5)
C11—C16	1.370 (8)	C200—Cl15	1.765 (5)
C11—C12	1.404 (8)	C200—Cl16	1.768 (5)
C12—C13	1.375 (8)	C200—H20A	0.9800
C12—H12A	0.9300	N300—C400	1.10 (2)
C13—C14	1.382 (9)	C400—C300	1.39 (2)
C13—H13A	0.9300	C300—H30A	0.9600
C14—O23	1.365 (6)	C300—H30B	0.9600
C14—C15	1.384 (8)	C300—H30C	0.9600
N2^i—Pt1—N2	180.00 (14)	C12—C13—C14	120.7 (6)
N2^i—Pt1—N1^i	90.07 (16)	C12—C13—H13A	119.6
N2—Pt1—N1^i	89.93 (16)	C14—C13—H13A	119.6
N2^i—Pt1—N1	89.93 (16)	O23—C14—C13	115.9 (5)
N2—Pt1—N1	90.07 (16)	O23—C14—C15	124.8 (6)
N1^i—Pt1—N1	180.0 (3)	C13—C14—C15	119.3 (5)
N2^i—Pt1—Br1	90.30 (13)	C16—C15—C14	119.4 (6)
N2—Pt1—Br1	89.70 (13)	C16—C15—H15A	120.3
N1^i—Pt1—Br1	91.13 (12)	C14—C15—H15A	120.3
N1—Pt1—Br1	88.87 (12)	C11—C16—C15	122.4 (6)
N2^i—Pt1—Br1^i	89.70 (13)	C11—C16—H16A	118.8
N2—Pt1—Br1^i	90.30 (13)	C15—C16—H16A	118.8
N1^i—Pt1—Br1^i	88.87 (12)	C22—C17—C18	118.9 (5)
N1—Pt1—Br1^i	91.13 (12)	C22—C17—C10	121.3 (5)
Br1—Pt1—Br1^i	180.00 (4)	C18—C17—C10	119.8 (5)
C1—N1—C4	107.4 (4)	C19—C18—C17	120.3 (5)
C1—N1—Pt1	126.6 (3)	C19—C18—H18A	119.8
C4—N1—Pt1	125.9 (3)	C17—C18—H18A	119.8
N1—C1—C10^i	126.2 (5)	C20—C19—C18	120.5 (6)
N1—C1—C2	108.7 (4)	C20—C19—H19A	119.8
C10^i—C1—C2	125.1 (5)	C18—C19—H19A	119.8
C9—N2—C6	107.2 (4)	O24—C20—C19	115.9 (5)
C9—N2—Pt1	126.6 (3)	O24—C20—C21	124.1 (6)
C6—N2—Pt1	126.1 (3)	C19—C20—C21	120.0 (5)
C3—C2—C1	107.9 (5)	C22—C21—C20	119.6 (6)
C3—C2—H2A	126.1	C22—C21—H21A	120.2
C1—C2—H2A	126.1	C20—C21—H21A	120.2
C2—C3—C4	107.7 (5)	C17—C22—C21	120.6 (5)
C2—C3—H3A	126.1	C17—C22—H22A	119.7
C4—C3—H3A	126.1	C21—C22—H22A	119.7
N1—C4—C5	126.7 (5)	C14—O23—C23	116.9 (5)
N1—C4—C3	108.3 (5)	O23—C23—H23A	109.5
C5—C4—C3	125.0 (5)	O23—C23—H23B	109.5
C4—C5—C6	124.7 (5)	H23A—C23—H23B	109.5
C4—C5—C11	117.8 (5)	O23—C23—H23C	109.5
C6—C5—C11	117.5 (5)	H23A—C23—H23C	109.5
N2—C6—C5	126.3 (5)	H23B—C23—H23C	109.5
N2—C6—C7	108.7 (4)	C20—O24—C24	118.0 (5)
C5—C6—C7	125.1 (5)	O24—C24—H24A	109.5
C8—C7—C6	107.4 (5)	O24—C24—H24B	109.5
C8—C7—H7A	126.3	H24A—C24—H24B	109.5
C6—C7—H7A	126.3	O24—C24—H24C	109.5
C7—C8—C9	108.1 (5)	H24A—C24—H24C	109.5
C7—C8—H8A	126.0	H24B—C24—H24C	109.5
C9—C8—H8A	126.0	Cl13—C100—Cl12	112.4 (5)
N2—C9—C10	125.9 (4)	Cl13—C100—Cl11	113.2 (5)
N2—C9—C8	108.7 (4)	Cl12—C100—Cl11	108.3 (7)
C10—C9—C8	125.4 (5)	Cl13—C100—H10A	107.5
C1^i—C10—C9	124.8 (5)	Cl12—C100—H10A	107.5
C1^i—C10—C17	117.7 (4)	Cl11—C100—H10A	107.5
C9—C10—C17	117.5 (4)	Cl14—C200—Cl15	108.4 (4)
C16—C11—C12	117.6 (5)	Cl14—C200—Cl16	109.6 (5)
C16—C11—C5	122.1 (5)	Cl15—C200—Cl16	110.6 (5)
C12—C11—C5	120.2 (5)	Cl14—C200—H20A	109.4
C13—C12—C11	120.5 (6)	Cl15—C200—H20A	109.4
C13—C12—H12A	119.8	Cl16—C200—H20A	109.4
C11—C12—H12A	119.8	N300—C400—C300	179 (3)

Symmetry code: (i) −x, −y, −z.