Twinned dichlorobis(2,6-dichloropyrazine-N⁴)zinc(II)

For crystals of the title compound, [ZnCl₂(C₄H₂Cl₂N₂)₂], metric considerations suggest a monoclinic unit cell. However, the symmetry of the diffraction pattern shows the crystals to be triclinic, with very similar lattice constants a and b, and α and β. All crystals ex­amined were twinned. The discrepancy between the reliability indices for merging in the monoclinic lattice metric symmetry and the triclinic crystal symmetry constitutes an indicator for the volume ratio between the components. The asymmetric unit contains three independent mol­ecules. At the molecular level, the compound shows a distorted tetrahedral coordination around one Zn atom.

S1. Comment

Our interest in intermolecular interactions recently induced us to synthesize and study the first one-dimensional chain polymers of the type [Zn(µ-Cl)₂py₂]_∞ (py is 3,5-dichloropyridine or 3,5-dibromopyridine), (II) (Hu & Englert, 2001). 2,6-Dichloropyrazine, the ligand involved in the present study, was expected to have similar steric requirements to the 3,5-dihalopyridines. Furthermore, coordination of a metal should only occur in the 4- and not in the 1-position. Despite these similarities between the dihalopyridine and dihalopyrazine ligands, reaction of zinc dichloride with the latter does not result in the formation of a chain polymer, but of the title tetrahedral mononuclear complex, (I), underlining the restricted range of existence for the above-mentioned type of coordination polymers. \sch

We studied five crystals of (I) by X-ray diffraction and obtained four data sets of comparable accuracy; the intensity data from a fifth sample proved to be less satisfactory in terms of internal consistency and will not be reported. All crystals were twinned. A metrically possible transformation to a monoclinic centred cell is incompatible with the symmetry of the diffraction pattern. The twinning can be classified as metric merohedry (Nespolo & Ferraris, 2000) with monoclinic lattice metric symmetry (LMS). Metric merohedry means that all reflections of the twin components will overlap. In other words, the reciprocal lattice of the twin mimics that of a single-crystal, and in the limiting case of a very small twin component twinning might be completely overlooked. In the present case, the twin law interchanges a and b according to the matrix (010, 100, 001). Internal agreement factors (R_int) for merging the intensity data under the LMS differ strongly between these independent data sets, and we wish to point out that this variation represents a warning sign for merohedral twinning. A synopsis of R_int, obtained under both the triclinic crystal symmetry and the monoclinic LMS, and the volume ratio between the twin components, is provided in Table 2. The discrepancy between R_int for merging in the LMS and the crystal symmetry may serve as an indicator for the volume ratio between the twin individuals. In the following discussion, in Table 1 and in the supplementary material, numerical values and their standard deviations refer to the data set with the smallest contribution of a second individual.

The asymmetric unit of (I) contains three independent molecules (Fig. 1). They are similar not only in terms of bond lengths and angles, but also with respect to the dihedral angles subtended by the planes through the pyrazine ligands [87.40 (18), 87.39 (18) and 89.64 (18)°]. A packing diagram is shown in Fig. 2. No particularly short intermolecular interactions occur; the shortest Cl···Cl distance is ca 3.39 Å.

Related literature

For related literature, see: Hu & Englert (2001); Nespolo & Ferraris (2000).

S2. Experimental

Colourless crystals of (I) were grown by slow evaporation from a solution of ZnCl₂ and 2,6-Cl₂-pyrazine (1:2) in ethanol under a flow of nitrogen.

S3. Refinement

All H atoms were introduced in idealized positions (C—H = 0.98 Å) and included as riding with U_iso(H) = 1.3U_eq(non-H).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT+ (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular view of (I) showing the three independent molecules. Displacement ellipsoids are at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing diagram for (I) along the c axis.

Dichlorobis(2,6-dichloropyrazine-N⁴)zinc(II)

Crystal data

[ZnCl2(C4H2Cl2N2)2]	Z = 6
Mr = 434.22	F(000) = 1272
Triclinic, P1	Dx = 1.903 Mg m^−3
a = 12.4478 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4880 (8) Å	Cell parameters from 31443 reflections
c = 15.6692 (9) Å	θ = 1.4–28.3°
α = 75.954 (1)°	µ = 2.67 mm^−1
β = 76.134 (1)°	T = 293 K
γ = 79.438 (1)°	Block, colourless
V = 2273.7 (2) Å^3	0.36 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	11257 independent reflections
Radiation source: fine-focus sealed tube	6480 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.398, Tmax = 0.587	k = −16→16
31443 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2) + (0.0309P)^2] where P = (Fo^2 + 2Fc^2)/3
11257 reflections	(Δ/σ)max = 0.001
515 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. The values of Tmin and Tmax are 0.718023 and 1.000000 from SADABS.

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
Zn1	0.69780 (3)	0.87835 (3)	0.24338 (3)	0.04852 (12)
Zn2	0.31282 (3)	0.15000 (3)	0.28837 (3)	0.04466 (11)
Zn3	0.99635 (3)	0.51099 (3)	0.21669 (3)	0.04580 (12)
Cl1	0.71674 (9)	0.76978 (9)	0.37249 (7)	0.0674 (3)
Cl2	0.80248 (8)	0.86944 (9)	0.11061 (7)	0.0664 (3)
Cl3	0.68225 (13)	1.33685 (10)	0.09425 (9)	0.0955 (4)
Cl4	0.53836 (12)	1.22161 (10)	0.43821 (8)	0.0930 (4)
Cl5	0.37496 (10)	0.89265 (11)	0.04109 (7)	0.0832 (4)
Cl6	0.25755 (9)	0.78485 (11)	0.38853 (7)	0.0770 (3)
Cl7	0.33155 (9)	0.04644 (8)	0.41871 (7)	0.0612 (3)
Cl8	0.42443 (8)	0.14275 (8)	0.15803 (6)	0.0568 (3)
Cl9	0.34596 (10)	0.60185 (9)	0.13283 (7)	0.0717 (3)
Cl10	0.18459 (11)	0.50373 (9)	0.47549 (7)	0.0810 (4)
Cl11	−0.02003 (11)	0.25743 (11)	0.08050 (8)	0.0898 (4)
Cl12	−0.13942 (9)	0.08871 (11)	0.41955 (7)	0.0756 (3)
Cl13	0.99787 (9)	0.39144 (8)	0.34470 (7)	0.0576 (3)
Cl14	1.10453 (9)	0.49922 (9)	0.08680 (7)	0.0657 (3)
Cl15	1.07935 (11)	0.95749 (9)	0.10210 (8)	0.0834 (4)
Cl16	0.97284 (10)	0.80013 (10)	0.44686 (7)	0.0798 (4)
Cl17	0.64420 (9)	0.67235 (10)	0.02764 (7)	0.0741 (3)
Cl18	0.53714 (9)	0.53455 (10)	0.37272 (8)	0.0798 (4)
N1	0.6746 (2)	1.0437 (2)	0.2562 (2)	0.0471 (8)
N2	0.6161 (3)	1.2652 (3)	0.2662 (2)	0.0625 (9)
N3	0.5395 (2)	0.8608 (2)	0.23055 (19)	0.0417 (7)
N4	0.3269 (3)	0.8406 (3)	0.2159 (2)	0.0531 (8)
N5	0.3029 (2)	0.3157 (2)	0.29860 (19)	0.0422 (7)
N6	0.2689 (3)	0.5382 (2)	0.3049 (2)	0.0520 (8)
N7	0.1527 (2)	0.1465 (2)	0.2706 (2)	0.0438 (7)
N8	−0.0667 (3)	0.1695 (3)	0.2509 (2)	0.0526 (8)
N9	1.0172 (2)	0.6626 (2)	0.24006 (19)	0.0427 (7)
N10	1.0256 (3)	0.8688 (3)	0.2731 (2)	0.0557 (8)
N11	0.8283 (2)	0.5395 (2)	0.20641 (19)	0.0448 (7)
N12	0.6051 (3)	0.5992 (3)	0.2001 (2)	0.0536 (8)
C1	0.6939 (3)	1.1248 (3)	0.1838 (3)	0.0548 (10)
H1	0.7303	1.1062	0.1255	0.071*
C2	0.6631 (3)	1.2341 (3)	0.1903 (3)	0.0569 (11)
C3	0.5997 (3)	1.1846 (3)	0.3372 (3)	0.0562 (10)
C4	0.6278 (3)	1.0733 (3)	0.3348 (3)	0.0529 (10)
H4	0.6138	1.0163	0.3901	0.069*
C5	0.5130 (3)	0.8786 (3)	0.1509 (2)	0.0441 (9)
H5	0.5688	0.8995	0.0960	0.057*
C6	0.4071 (3)	0.8679 (3)	0.1452 (2)	0.0484 (9)
C7	0.3567 (3)	0.8227 (3)	0.2940 (2)	0.0478 (9)
C8	0.4614 (3)	0.8325 (3)	0.3040 (2)	0.0472 (9)
H8	0.4782	0.8191	0.3640	0.061*
C9	0.3279 (3)	0.3931 (3)	0.2241 (2)	0.0474 (9)
H9	0.3575	0.3712	0.1660	0.062*
C10	0.3120 (3)	0.5036 (3)	0.2291 (2)	0.0462 (9)
C11	0.2457 (3)	0.4607 (3)	0.3762 (2)	0.0484 (9)
C12	0.2633 (3)	0.3481 (3)	0.3764 (2)	0.0449 (9)
H12	0.2469	0.2932	0.4326	0.058*
C13	0.1243 (3)	0.1909 (3)	0.1906 (3)	0.0530 (10)
H13	0.1815	0.2160	0.1379	0.069*
C14	0.0158 (3)	0.2011 (3)	0.1828 (3)	0.0540 (10)
C15	−0.0360 (3)	0.1263 (3)	0.3287 (2)	0.0464 (9)
C16	0.0727 (3)	0.1132 (3)	0.3398 (2)	0.0443 (9)
H16	0.0907	0.0792	0.3989	0.058*
C17	1.0447 (3)	0.7472 (3)	0.1734 (2)	0.0483 (9)
H17	1.0627	0.7373	0.1112	0.063*
C18	1.0480 (3)	0.8490 (3)	0.1909 (3)	0.0504 (10)
C19	1.0007 (3)	0.7828 (3)	0.3380 (3)	0.0505 (10)
C20	0.9948 (3)	0.6794 (3)	0.3242 (2)	0.0456 (9)
H20	0.9745	0.6186	0.3754	0.059*
C21	0.7970 (3)	0.5831 (3)	0.1287 (2)	0.0464 (9)
H21	0.8529	0.5945	0.0726	0.060*
C22	0.6851 (3)	0.6122 (3)	0.1277 (3)	0.0500 (10)
C23	0.6386 (3)	0.5530 (3)	0.2760 (3)	0.0512 (10)
C24	0.7491 (3)	0.5231 (3)	0.2812 (3)	0.0513 (10)
H24	0.7698	0.4898	0.3394	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0427 (3)	0.0440 (2)	0.0577 (3)	−0.00338 (19)	−0.0124 (2)	−0.0081 (2)
Zn2	0.0441 (3)	0.0397 (2)	0.0465 (3)	−0.00325 (19)	−0.0053 (2)	−0.0076 (2)
Zn3	0.0494 (3)	0.0440 (2)	0.0455 (3)	0.0009 (2)	−0.0132 (2)	−0.0141 (2)
Cl1	0.0674 (7)	0.0678 (7)	0.0636 (7)	−0.0012 (6)	−0.0266 (6)	0.0001 (6)
Cl2	0.0498 (6)	0.0742 (7)	0.0678 (7)	−0.0065 (5)	0.0024 (5)	−0.0160 (6)
Cl3	0.1446 (13)	0.0554 (7)	0.0773 (9)	−0.0239 (7)	−0.0212 (8)	0.0094 (6)
Cl4	0.1363 (12)	0.0781 (8)	0.0651 (8)	0.0123 (8)	−0.0284 (8)	−0.0282 (7)
Cl5	0.0848 (8)	0.1192 (10)	0.0502 (7)	−0.0306 (7)	−0.0270 (6)	−0.0008 (7)
Cl6	0.0692 (7)	0.1116 (9)	0.0542 (7)	−0.0437 (7)	0.0138 (5)	−0.0276 (7)
Cl7	0.0709 (7)	0.0541 (6)	0.0521 (6)	−0.0095 (5)	−0.0140 (5)	0.0033 (5)
Cl8	0.0536 (6)	0.0572 (6)	0.0504 (6)	0.0039 (5)	0.0003 (5)	−0.0131 (5)
Cl9	0.1060 (9)	0.0579 (6)	0.0510 (6)	−0.0336 (6)	−0.0150 (6)	0.0049 (5)
Cl10	0.1290 (11)	0.0618 (7)	0.0473 (7)	−0.0117 (7)	−0.0017 (7)	−0.0190 (5)
Cl11	0.1017 (10)	0.1114 (10)	0.0609 (8)	−0.0313 (8)	−0.0413 (7)	0.0105 (7)
Cl12	0.0508 (6)	0.1122 (9)	0.0586 (7)	−0.0246 (6)	0.0002 (5)	−0.0092 (6)
Cl13	0.0718 (7)	0.0451 (5)	0.0540 (6)	0.0029 (5)	−0.0216 (5)	−0.0061 (5)
Cl14	0.0668 (7)	0.0786 (7)	0.0540 (6)	−0.0065 (6)	−0.0019 (5)	−0.0307 (6)
Cl15	0.1020 (10)	0.0591 (7)	0.0849 (9)	−0.0280 (6)	−0.0241 (7)	0.0109 (6)
Cl16	0.0837 (8)	0.1051 (9)	0.0636 (7)	−0.0230 (7)	0.0006 (6)	−0.0494 (7)
Cl17	0.0694 (7)	0.0970 (9)	0.0537 (7)	0.0147 (6)	−0.0266 (5)	−0.0167 (6)
Cl18	0.0634 (7)	0.0951 (9)	0.0660 (8)	−0.0119 (6)	0.0049 (6)	−0.0054 (7)
N1	0.0476 (19)	0.0442 (18)	0.054 (2)	−0.0073 (14)	−0.0197 (16)	−0.0082 (16)
N2	0.081 (3)	0.046 (2)	0.065 (2)	−0.0041 (18)	−0.031 (2)	−0.0092 (19)
N3	0.0402 (17)	0.0398 (16)	0.0445 (19)	−0.0038 (13)	−0.0068 (14)	−0.0103 (14)
N4	0.046 (2)	0.058 (2)	0.057 (2)	−0.0107 (16)	−0.0085 (17)	−0.0149 (17)
N5	0.0417 (17)	0.0395 (17)	0.0426 (18)	−0.0069 (13)	−0.0061 (14)	−0.0046 (14)
N6	0.068 (2)	0.0454 (18)	0.045 (2)	−0.0092 (16)	−0.0144 (17)	−0.0107 (16)
N7	0.0473 (18)	0.0408 (17)	0.0426 (19)	−0.0084 (14)	−0.0070 (15)	−0.0073 (14)
N8	0.056 (2)	0.056 (2)	0.052 (2)	−0.0139 (16)	−0.0170 (17)	−0.0124 (17)
N9	0.0433 (18)	0.0394 (17)	0.0439 (19)	0.0005 (13)	−0.0102 (14)	−0.0086 (15)
N10	0.054 (2)	0.053 (2)	0.066 (2)	−0.0078 (16)	−0.0142 (18)	−0.0223 (19)
N11	0.0468 (19)	0.0438 (17)	0.0442 (19)	−0.0017 (14)	−0.0104 (15)	−0.0121 (15)
N12	0.051 (2)	0.056 (2)	0.055 (2)	−0.0016 (16)	−0.0161 (17)	−0.0136 (17)
C1	0.060 (3)	0.053 (3)	0.052 (3)	−0.012 (2)	−0.015 (2)	−0.005 (2)
C2	0.072 (3)	0.043 (2)	0.060 (3)	−0.013 (2)	−0.023 (2)	−0.003 (2)
C3	0.064 (3)	0.055 (3)	0.057 (3)	0.002 (2)	−0.029 (2)	−0.016 (2)
C4	0.058 (3)	0.052 (2)	0.054 (3)	−0.008 (2)	−0.023 (2)	−0.008 (2)
C5	0.045 (2)	0.041 (2)	0.042 (2)	−0.0063 (17)	−0.0037 (17)	−0.0059 (17)
C6	0.051 (2)	0.050 (2)	0.044 (2)	−0.0077 (18)	−0.0109 (19)	−0.0089 (18)
C7	0.044 (2)	0.053 (2)	0.046 (2)	−0.0144 (18)	0.0046 (18)	−0.0171 (19)
C8	0.053 (2)	0.046 (2)	0.042 (2)	−0.0069 (18)	−0.0060 (19)	−0.0118 (18)
C9	0.049 (2)	0.049 (2)	0.044 (2)	−0.0069 (18)	−0.0064 (18)	−0.0130 (19)
C10	0.052 (2)	0.045 (2)	0.040 (2)	−0.0131 (18)	−0.0094 (18)	0.0008 (18)
C11	0.059 (2)	0.048 (2)	0.041 (2)	−0.0084 (19)	−0.0122 (19)	−0.0108 (19)
C12	0.051 (2)	0.046 (2)	0.036 (2)	−0.0052 (18)	−0.0094 (17)	−0.0054 (17)
C13	0.057 (3)	0.055 (2)	0.046 (2)	−0.012 (2)	−0.005 (2)	−0.011 (2)
C14	0.062 (3)	0.056 (2)	0.049 (3)	−0.012 (2)	−0.018 (2)	−0.010 (2)
C15	0.042 (2)	0.052 (2)	0.046 (2)	−0.0118 (18)	−0.0048 (18)	−0.0138 (19)
C16	0.046 (2)	0.045 (2)	0.041 (2)	−0.0064 (17)	−0.0078 (18)	−0.0097 (17)
C17	0.051 (2)	0.050 (2)	0.044 (2)	−0.0004 (18)	−0.0131 (18)	−0.0096 (19)
C18	0.044 (2)	0.044 (2)	0.060 (3)	−0.0045 (17)	−0.0151 (19)	−0.003 (2)
C19	0.040 (2)	0.063 (3)	0.050 (2)	−0.0036 (19)	−0.0063 (18)	−0.022 (2)
C20	0.046 (2)	0.049 (2)	0.043 (2)	−0.0042 (17)	−0.0075 (17)	−0.0140 (18)
C21	0.054 (2)	0.047 (2)	0.040 (2)	−0.0015 (18)	−0.0120 (18)	−0.0143 (18)
C22	0.058 (3)	0.049 (2)	0.048 (2)	0.0042 (19)	−0.019 (2)	−0.0186 (19)
C23	0.052 (3)	0.046 (2)	0.053 (3)	−0.0095 (19)	−0.002 (2)	−0.0118 (19)
C24	0.058 (3)	0.054 (2)	0.042 (2)	−0.005 (2)	−0.014 (2)	−0.0079 (19)

Geometric parameters (Å, º)

Zn1—N1	2.084 (3)	N7—C16	1.325 (4)
Zn1—N3	2.084 (3)	N7—C13	1.344 (4)
Zn2—N5	2.094 (3)	N8—C15	1.324 (4)
Zn2—N7	2.086 (3)	N8—C14	1.329 (5)
Zn3—N9	2.085 (3)	N9—C17	1.323 (4)
Zn3—N11	2.095 (3)	N9—C20	1.340 (4)
Zn1—Cl1	2.1833 (11)	N10—C19	1.313 (5)
Zn1—Cl2	2.1905 (11)	N10—C18	1.325 (5)
Zn2—Cl7	2.1757 (10)	N11—C21	1.326 (4)
Zn2—Cl8	2.1894 (10)	N11—C24	1.339 (4)
Zn3—Cl13	2.1924 (10)	N12—C22	1.316 (5)
Zn3—Cl14	2.1764 (11)	N12—C23	1.318 (5)
Cl3—C2	1.723 (4)	C1—C2	1.370 (5)
Cl4—C3	1.718 (4)	C1—H1	0.9800
Cl5—C6	1.714 (4)	C3—C4	1.377 (5)
Cl6—C7	1.714 (4)	C4—H4	0.9800
Cl9—C10	1.716 (3)	C5—C6	1.375 (5)
Cl10—C11	1.725 (4)	C5—H5	0.9800
Cl11—C14	1.716 (4)	C7—C8	1.380 (5)
Cl12—C15	1.709 (4)	C8—H8	0.9800
Cl15—C18	1.715 (4)	C9—C10	1.376 (5)
Cl16—C19	1.716 (4)	C9—H9	0.9800
Cl17—C22	1.718 (4)	C11—C12	1.382 (5)
Cl18—C23	1.721 (4)	C12—H12	0.9800
N1—C1	1.331 (4)	C13—C14	1.366 (5)
N1—C4	1.338 (4)	C13—H13	0.9800
N2—C2	1.310 (5)	C15—C16	1.381 (5)
N2—C3	1.309 (5)	C16—H16	0.9800
N3—C5	1.324 (4)	C17—C18	1.373 (5)
N3—C8	1.337 (4)	C17—H17	0.9800
N4—C7	1.318 (4)	C19—C20	1.379 (5)
N4—C6	1.323 (4)	C20—H20	0.9800
N5—C12	1.330 (4)	C21—C22	1.377 (5)
N5—C9	1.335 (4)	C21—H21	0.9800
N6—C11	1.302 (4)	C23—C24	1.374 (5)
N6—C10	1.321 (4)	C24—H24	0.9800
N1—Zn1—N3	101.30 (11)	N4—C6—C5	123.8 (4)
N5—Zn2—N7	101.26 (11)	N4—C6—Cl5	117.4 (3)
N9—Zn3—N11	101.53 (11)	C5—C6—Cl5	118.9 (3)
Cl1—Zn1—Cl2	127.86 (5)	N4—C7—C8	124.3 (3)
Cl7—Zn2—Cl8	127.53 (4)	N4—C7—Cl6	117.1 (3)
Cl13—Zn3—Cl14	127.47 (4)	C8—C7—Cl6	118.6 (3)
N3—Zn1—Cl1	104.02 (8)	N3—C8—C7	118.9 (3)
N1—Zn1—Cl1	108.99 (9)	N3—C8—H8	120.5
N3—Zn1—Cl2	103.96 (8)	C7—C8—H8	120.5
N1—Zn1—Cl2	107.43 (9)	N5—C9—C10	119.7 (3)
N7—Zn2—Cl7	108.37 (9)	N5—C9—H9	120.1
N5—Zn2—Cl7	107.06 (8)	C10—C9—H9	120.1
N7—Zn2—Cl8	106.07 (9)	N6—C10—C9	122.8 (3)
N5—Zn2—Cl8	103.54 (8)	N6—C10—Cl9	118.0 (3)
N9—Zn3—Cl14	104.94 (9)	C9—C10—Cl9	119.2 (3)
N11—Zn3—Cl14	110.53 (9)	N6—C11—C12	124.3 (3)
N9—Zn3—Cl13	105.69 (8)	N6—C11—Cl10	116.8 (3)
N11—Zn3—Cl13	103.80 (9)	C12—C11—Cl10	118.9 (3)
C1—N1—C4	117.6 (3)	N5—C12—C11	118.7 (3)
C1—N1—Zn1	120.3 (3)	N5—C12—H12	120.7
C4—N1—Zn1	121.6 (3)	C11—C12—H12	120.7
C2—N2—C3	115.7 (3)	N7—C13—C14	120.0 (4)
C5—N3—C8	118.5 (3)	N7—C13—H13	120.0
C5—N3—Zn1	121.6 (2)	C14—C13—H13	120.0
C8—N3—Zn1	119.9 (2)	N8—C14—C13	123.8 (4)
C7—N4—C6	114.6 (3)	N8—C14—Cl11	116.4 (3)
C12—N5—C9	118.6 (3)	C13—C14—Cl11	119.8 (3)
C12—N5—Zn2	121.9 (2)	N8—C15—C16	123.6 (3)
C9—N5—Zn2	119.3 (2)	N8—C15—Cl12	116.8 (3)
C11—N6—C10	115.8 (3)	C16—C15—Cl12	119.5 (3)
C16—N7—C13	117.9 (3)	N7—C16—C15	120.0 (3)
C16—N7—Zn2	121.1 (2)	N7—C16—H16	120.0
C13—N7—Zn2	120.6 (2)	C15—C16—H16	120.0
C15—N8—C14	114.8 (3)	N9—C17—C18	120.4 (3)
C17—N9—C20	117.9 (3)	N9—C17—H17	119.8
C17—N9—Zn3	121.9 (2)	C18—C17—H17	119.8
C20—N9—Zn3	120.1 (2)	N10—C18—C17	123.4 (4)
C19—N10—C18	114.9 (3)	N10—C18—Cl15	117.9 (3)
C21—N11—C24	118.4 (3)	C17—C18—Cl15	118.7 (3)
C21—N11—Zn3	122.0 (2)	N10—C19—C20	124.1 (4)
C24—N11—Zn3	119.4 (2)	N10—C19—Cl16	118.2 (3)
C22—N12—C23	115.4 (3)	C20—C19—Cl16	117.8 (3)
N1—C1—C2	120.4 (4)	N9—C20—C19	119.4 (3)
N1—C1—H1	119.8	N9—C20—H20	120.3
C2—C1—H1	119.8	C19—C20—H20	120.3
N2—C2—C1	123.1 (4)	N11—C21—C22	119.3 (3)
N2—C2—Cl3	117.6 (3)	N11—C21—H21	120.4
C1—C2—Cl3	119.3 (3)	C22—C21—H21	120.4
N2—C3—C4	123.8 (4)	N12—C22—C21	123.9 (4)
N2—C3—Cl4	117.3 (3)	N12—C22—Cl17	116.6 (3)
C4—C3—Cl4	118.9 (3)	C21—C22—Cl17	119.5 (3)
N1—C4—C3	119.2 (4)	N12—C23—C24	123.2 (4)
N1—C4—H4	120.4	N12—C23—Cl18	117.2 (3)
C3—C4—H4	120.4	C24—C23—Cl18	119.6 (3)
N3—C5—C6	119.9 (3)	N11—C24—C23	119.7 (3)
N3—C5—H5	120.0	N11—C24—H24	120.1
C6—C5—H5	120.0	C23—C24—H24	120.1