Bis(2-benzyl-1H-benz­imidazole-N³)dichorozinc(II)

In the title compound, [ZnCl₂(C₁₄H₁₂N₂)₂], the environment around the Zn atom is distorted tetrahedral formed by two Cl atoms and two tertiary N atoms of the 2-benzyl-1H-benz­imidazole ligands. N—H...Cl intermolecular hydrogen bonds link the mol­ecules into infinite chains in the [101] direction.

S1. Comment

Benzimidazole is an interesting heterocyclic ring because it is present in various naturally occurring drugs, such as omeprazole, astemizole and emedastine difumarate (Sakai et al., 1989). The efficacy of substituted benzimidazoles in the treatment of parasitic infections is well known (Brown et al., 1961; Preston, 1974; Sarkar et al., 1984). Benzimidazole-substituted moieties are established pharmacophores in parasitic chemotherapy. Bis(2-benzimidazoles) and some substituted bis(2-benzimidazolyl)alkanes have attracted much interest because of their wide-ranging antiviral activity (Tidwell, et al., 1993) and also because of the coordination chemistry of azoles acting as ligands in transition-metal compounds. Such compounds are increasingly being studied in the context of modelling biological systems (Pujar et al., 1988; Bouwman et al., 1990). Zinc is a relatively abundant element in biological organisms and plays an essential role in a large number of enzymatic reactions (Liljas et al., 1972). Zinc(II), being a d¹⁰ ion, provides few spectroscopic signatures for the monitoring of structure. The structure of the zinc binding site can only be elucidated by X-ray crystallography. \scheme I

In the title compound, (I), the molecule possesses near C₂ symmetry and the symmetry axis lies parallel to the b axis. The Zn atom is coordinated tetrahedrally by two Cl anions and two 2-benzyl-1H-benzimidazole ligands, i.e. ZnCl₂N₂. The ZnCl₂N₂ tetrahedron is slightly distorted, with angles ranging from 103.32 (7) to 116.67 (7) Å. The range of the tetrahedral angles are comparable with the corresponding values in the reported complex ZnCl₂(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)₂ [102.09 (9)–117.54 (4) Å; Salas et al., 1994] but the coordination around Zn in another complex, which also contains the ZnCl₂N₂ unit, namely ZnCl₂[purine]₂ (Laity & Taylor, 1995), is severely distorted compared with the title complex, with the angles ranging from 99.9 (1) to 113.7 (1) Å. \scheme

The average Zn—Cl distance of 2.261 (1) Å is longer than the average corresponding distances reported for related metal complexes with distorted ZnN₂Cl₂ tetrahedral environments, cf. 2.224 (1) Å in ZnCl₂(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)₂ (Salas et al., 1994), 2.212 (4) Å in ZnCl₂(2,9-dimethyl-1,10-phenanthroline) (Preston & Kennard, 1969), 2.226 (2) Å in ZnCl₂(purine)₂ (Laity & Taylor, 1995) and 2.209 (3) Å in ZnCl₂(4-vinylpyridine)₂ (Steffen & Palenik, 1977), but comparable to 2.255 (1) Å in ZnCl₂[1-(5,6-dimethyl-1H-benzimidazolyl)- 3-(1,3-benzimidazolyl)-2-thiapropane] (Matthews et al., 1998).

The average Zn—N bond distance of 2.042 (3) Å is comparable to the reported average values, e.g. 2.039 (3) Å in ZnCl₂(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)₂ (Salas et al., 1994), 2.05 (1) Å in ZnCl₂(1-methyltetrazole)₂ (Baenziger & Schultz, 1971), 2.059 (3) Å in ZnCl₂(1-methylcytosine)₂ (Beauchamp, 1984) and 2.027 (3) Å in ZnCl₂[1-(5,6-dimethyl-1H-benzimidazolyl)-3-benzimidazolyl-2-thiapropane] (Matthews et al., 1998), but longer than the average value of 2.007 (4) Å in Zn_0.99Cu_0.01Cl₂[1,2-dimethylimidazole]₂ (Bharadwaj et al., 1991).

The dihedral angles between the benzimidazole moieties (involving N1/N2 and N3/N4) and the phenyl rings (C9–C14 and C23–C28) are 83.0 (2) and 79.4 (2)°, respectively. The mean planes of the two benzimidazole moieties form a dihedral angle of 69.7 (1)°, while the dihedral angle between the phenyl rings is 1.2 (2)°.

In the crystal, the N atoms (N2 and N4) from both benzimidazole moieties are involved in N—H···Cl intermolecular hydrogen bonds with the Cl atoms (Table 2). These intermolecular hydrogen bonds link the molecules into infinite one-dimensional chains in the [101] direction.

S2. Experimental

Solid 2-benzyl-2-benzimidazole was dissolved in EtOH/H₂O. Zinc dichloride was then added at 343–353 K with stirring, refluxing for 4–5 h and then cooling. The red solution obtained was filtered and left for evaporation. After one day, the red solids were separated out and were recrystallized from EtOH/H₂O. Single crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature from the EtOH solvent.

S3. Refinement

After checking their presence in the difference map, the positions of all H atoms were calculated geometrically and allowed to ride on their attached atoms (N—H = 0.00 Å and C—H = 0.00–0.00 Å). The highest peak and deepest hole are located 0.91 and 0.82 Å, respectively, from the Zn atom. Examination of the structure with PLATON (Spek, 1990) showed that there were solvent accessible voids of 34 ų in the crystal lattice, but there was no evidence of diffuse solvent in those holes.

Computing details

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

Figures

Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Dichorobis(2-benzyl)benzimidazolo Zinc(II)

Crystal data

[ZnCl2(C14H12N2)2]	F(000) = 1136
Mr = 552.78	Dx = 1.438 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.8623 (2) Å	Cell parameters from 8192 reflections
b = 16.3674 (1) Å	θ = 1.9–28.3°
c = 14.1767 (2) Å	µ = 1.20 mm^−1
β = 111.943 (1)°	T = 293 K
V = 2553.08 (6) Å^3	Slab, red
Z = 4	0.28 × 0.24 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer	6226 independent reflections
Radiation source: fine-focus sealed tube	3898 reflections with I > 2σ(I)'
Graphite monochromator	Rint = 0.073
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.9°
ω scans	h = −7→15
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −21→21
Tmin = 0.731, Tmax = 0.796	l = −18→18
17665 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0592P)^2] where P = (Fo^2 + 2Fc^2)/3
6226 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −1.51 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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	0.17445 (3)	0.22953 (2)	0.46297 (2)	0.03183 (12)
Cl1	0.10770 (7)	0.15171 (5)	0.56294 (6)	0.0449 (2)
Cl2	0.24012 (7)	0.14669 (5)	0.36634 (6)	0.0447 (2)
N1	0.3046 (2)	0.30088 (14)	0.56451 (17)	0.0327 (5)
N2	0.4786 (2)	0.34242 (15)	0.68028 (17)	0.0376 (6)
H2A	0.5555	0.3494	0.7112	0.045*
N3	0.0493 (2)	0.30382 (14)	0.36063 (16)	0.0307 (5)
N4	−0.1210 (2)	0.35521 (15)	0.24906 (18)	0.0392 (6)
H4A	−0.1972	0.3657	0.2191	0.047*
C1	0.2795 (3)	0.34761 (17)	0.6377 (2)	0.0335 (6)
C2	0.1691 (3)	0.36735 (19)	0.6455 (2)	0.0450 (8)
H2B	0.0953	0.3501	0.5975	0.054*
C3	0.1756 (3)	0.4145 (2)	0.7298 (3)	0.0524 (9)
H3A	0.1039	0.4292	0.7376	0.063*
C4	0.2858 (3)	0.4402 (2)	0.8022 (3)	0.0511 (9)
H4B	0.2857	0.4716	0.8568	0.061*
C5	0.3954 (3)	0.42005 (19)	0.7948 (2)	0.0449 (8)
H5A	0.4692	0.4369	0.8433	0.054*
C6	0.3897 (3)	0.37346 (17)	0.7114 (2)	0.0352 (7)
C7	0.4253 (3)	0.29962 (18)	0.5939 (2)	0.0348 (7)
C8	0.4942 (3)	0.25770 (19)	0.5405 (2)	0.0404 (7)
H8A	0.4556	0.2055	0.5159	0.049*
H8B	0.5754	0.2466	0.5891	0.049*
C9	0.5048 (3)	0.30437 (19)	0.4510 (2)	0.0349 (6)
C10	0.5147 (3)	0.2618 (2)	0.3712 (2)	0.0432 (7)
H10A	0.5118	0.2050	0.3716	0.052*
C11	0.5289 (3)	0.3016 (2)	0.2899 (2)	0.0514 (9)
H11A	0.5363	0.2716	0.2368	0.062*
C12	0.5320 (4)	0.3845 (2)	0.2882 (3)	0.0602 (10)
H12A	0.5414	0.4116	0.2340	0.072*
C13	0.5211 (4)	0.4281 (2)	0.3672 (3)	0.0726 (13)
H13A	0.5230	0.4849	0.3661	0.087*
C14	0.5072 (4)	0.3878 (2)	0.4487 (3)	0.0564 (10)
H14A	0.4996	0.4178	0.5017	0.068*
C15	0.0777 (3)	0.34993 (16)	0.28891 (19)	0.0322 (6)
C16	0.1892 (3)	0.36436 (19)	0.2800 (2)	0.0423 (7)
H16A	0.2612	0.3420	0.3253	0.051*
C17	0.1868 (3)	0.4140 (2)	0.2000 (3)	0.0515 (9)
H17A	0.2593	0.4249	0.1914	0.062*
C18	0.0803 (3)	0.4479 (2)	0.1324 (2)	0.0515 (9)
H18A	0.0839	0.4817	0.0808	0.062*
C19	−0.0311 (3)	0.4331 (2)	0.1391 (2)	0.0481 (8)
H19A	−0.1027	0.4554	0.0932	0.058*
C20	−0.0301 (3)	0.38274 (17)	0.2191 (2)	0.0355 (7)
C21	−0.0705 (3)	0.30873 (18)	0.3338 (2)	0.0335 (6)
C22	−0.1438 (3)	0.27260 (19)	0.3884 (2)	0.0392 (7)
H22A	−0.1074	0.2210	0.4180	0.047*
H22B	−0.2247	0.2611	0.3394	0.047*
C23	−0.1545 (3)	0.32648 (19)	0.4719 (2)	0.0375 (7)
C24	−0.1701 (3)	0.2907 (2)	0.5537 (2)	0.0487 (8)
H24A	−0.1726	0.2341	0.5576	0.058*
C25	−0.1823 (3)	0.3379 (3)	0.6309 (3)	0.0624 (11)
H25A	−0.1921	0.3127	0.6861	0.075*
C26	−0.1800 (4)	0.4212 (3)	0.6260 (3)	0.0717 (12)
H26A	−0.1896	0.4529	0.6769	0.086*
C27	−0.1635 (4)	0.4574 (3)	0.5455 (3)	0.0737 (13)
H27A	−0.1610	0.5141	0.5422	0.088*
C28	−0.1502 (4)	0.4108 (2)	0.4681 (3)	0.0562 (10)
H28A	−0.1385	0.4364	0.4139	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0340 (2)	0.0373 (2)	0.02325 (16)	0.00336 (15)	0.00968 (13)	0.00198 (14)
Cl1	0.0455 (5)	0.0548 (5)	0.0348 (4)	−0.0050 (4)	0.0156 (3)	0.0096 (3)
Cl2	0.0441 (4)	0.0534 (5)	0.0370 (4)	0.0117 (4)	0.0156 (3)	−0.0055 (3)
N1	0.0333 (13)	0.0368 (13)	0.0274 (11)	−0.0001 (11)	0.0107 (10)	0.0030 (10)
N2	0.0328 (14)	0.0442 (15)	0.0308 (12)	−0.0071 (11)	0.0059 (11)	0.0059 (11)
N3	0.0322 (13)	0.0327 (12)	0.0274 (11)	0.0038 (10)	0.0115 (10)	−0.0028 (10)
N4	0.0353 (14)	0.0460 (15)	0.0315 (12)	0.0111 (12)	0.0070 (11)	−0.0011 (11)
C1	0.0393 (17)	0.0318 (16)	0.0283 (14)	0.0004 (13)	0.0113 (13)	0.0050 (12)
C2	0.0446 (19)	0.0457 (19)	0.0443 (18)	0.0033 (15)	0.0161 (16)	−0.0013 (15)
C3	0.060 (2)	0.047 (2)	0.057 (2)	0.0065 (17)	0.0307 (19)	−0.0037 (17)
C4	0.070 (3)	0.0408 (19)	0.0428 (18)	−0.0004 (18)	0.0219 (18)	−0.0054 (15)
C5	0.057 (2)	0.0387 (18)	0.0338 (16)	−0.0094 (16)	0.0108 (15)	0.0011 (14)
C6	0.0451 (17)	0.0320 (15)	0.0300 (14)	−0.0048 (13)	0.0158 (13)	0.0049 (12)
C7	0.0386 (17)	0.0348 (16)	0.0295 (14)	−0.0009 (13)	0.0108 (13)	0.0105 (12)
C8	0.0391 (17)	0.0455 (18)	0.0379 (16)	0.0067 (14)	0.0157 (14)	0.0094 (14)
C9	0.0315 (15)	0.0423 (17)	0.0338 (14)	−0.0009 (13)	0.0158 (13)	0.0042 (13)
C10	0.0422 (18)	0.0447 (18)	0.0461 (18)	−0.0009 (15)	0.0204 (15)	−0.0015 (15)
C11	0.050 (2)	0.071 (2)	0.0388 (17)	−0.0070 (18)	0.0226 (16)	−0.0099 (17)
C12	0.082 (3)	0.063 (2)	0.048 (2)	−0.008 (2)	0.039 (2)	0.0066 (19)
C13	0.128 (4)	0.042 (2)	0.074 (3)	−0.011 (2)	0.068 (3)	0.0020 (19)
C14	0.090 (3)	0.045 (2)	0.051 (2)	−0.007 (2)	0.046 (2)	−0.0031 (17)
C15	0.0393 (17)	0.0311 (15)	0.0244 (13)	0.0025 (12)	0.0098 (12)	−0.0021 (11)
C16	0.0424 (18)	0.0462 (19)	0.0371 (16)	−0.0024 (15)	0.0136 (15)	0.0003 (14)
C17	0.060 (2)	0.053 (2)	0.0476 (19)	−0.0079 (18)	0.0261 (18)	0.0019 (16)
C18	0.069 (2)	0.048 (2)	0.0374 (17)	−0.0019 (18)	0.0191 (17)	0.0089 (15)
C19	0.065 (2)	0.0432 (19)	0.0290 (15)	0.0116 (17)	0.0093 (15)	0.0058 (14)
C20	0.0425 (17)	0.0351 (16)	0.0263 (13)	0.0058 (14)	0.0098 (13)	−0.0048 (12)
C21	0.0366 (16)	0.0332 (15)	0.0263 (13)	0.0073 (13)	0.0068 (12)	−0.0050 (12)
C22	0.0346 (16)	0.0424 (18)	0.0412 (16)	0.0015 (14)	0.0150 (14)	−0.0043 (14)
C23	0.0336 (16)	0.0444 (18)	0.0359 (15)	0.0056 (14)	0.0145 (13)	−0.0059 (14)
C24	0.047 (2)	0.057 (2)	0.0433 (18)	0.0043 (16)	0.0190 (16)	0.0018 (15)
C25	0.057 (2)	0.098 (3)	0.0372 (18)	0.013 (2)	0.0228 (17)	0.001 (2)
C26	0.077 (3)	0.094 (3)	0.045 (2)	0.017 (3)	0.023 (2)	−0.023 (2)
C27	0.101 (4)	0.055 (2)	0.068 (3)	0.010 (2)	0.034 (3)	−0.018 (2)
C28	0.079 (3)	0.049 (2)	0.0465 (19)	0.0044 (19)	0.030 (2)	−0.0064 (17)

Geometric parameters (Å, º)

Zn1—N1	2.039 (2)	C9—C14	1.367 (4)
Zn1—N3	2.044 (2)	C9—C10	1.370 (4)
Zn1—Cl1	2.2575 (8)	C10—C11	1.389 (5)
Zn1—Cl2	2.2626 (8)	C11—C12	1.358 (5)
N1—C7	1.334 (4)	C12—C13	1.373 (5)
N1—C1	1.407 (4)	C13—C14	1.393 (5)
N2—C7	1.346 (4)	C15—C16	1.395 (4)
N2—C6	1.383 (4)	C15—C20	1.399 (4)
N3—C21	1.329 (4)	C16—C17	1.388 (4)
N3—C15	1.405 (3)	C17—C18	1.384 (5)
N4—C21	1.358 (4)	C18—C19	1.382 (5)
N4—C20	1.375 (4)	C19—C20	1.398 (4)
C1—C2	1.393 (4)	C21—C22	1.485 (4)
C1—C6	1.400 (4)	C22—C23	1.519 (4)
C2—C3	1.400 (4)	C23—C24	1.373 (4)
C3—C4	1.391 (5)	C23—C28	1.383 (4)
C4—C5	1.382 (5)	C24—C25	1.390 (5)
C5—C6	1.387 (4)	C25—C26	1.366 (6)
C7—C8	1.474 (4)	C26—C27	1.363 (5)
C8—C9	1.527 (4)	C27—C28	1.392 (5)
N1—Zn1—N3	108.54 (9)	C14—C9—C8	121.9 (3)
N1—Zn1—Cl1	103.32 (7)	C10—C9—C8	119.4 (3)
N3—Zn1—Cl1	116.67 (7)	C9—C10—C11	121.4 (3)
N1—Zn1—Cl2	115.44 (7)	C12—C11—C10	119.7 (3)
N3—Zn1—Cl2	104.47 (6)	C11—C12—C13	119.6 (3)
Cl1—Zn1—Cl2	108.84 (3)	C12—C13—C14	120.5 (3)
C7—N1—C1	106.0 (2)	C9—C14—C13	120.2 (3)
C7—N1—Zn1	130.8 (2)	C16—C15—C20	121.2 (3)
C1—N1—Zn1	121.27 (19)	C16—C15—N3	130.4 (3)
C7—N2—C6	109.1 (2)	C20—C15—N3	108.4 (2)
C21—N3—C15	106.3 (2)	C17—C16—C15	116.3 (3)
C21—N3—Zn1	130.9 (2)	C18—C17—C16	122.4 (3)
C15—N3—Zn1	121.73 (18)	C19—C18—C17	122.0 (3)
C21—N4—C20	108.6 (2)	C18—C19—C20	116.2 (3)
C2—C1—C6	120.9 (3)	N4—C20—C19	132.4 (3)
C2—C1—N1	130.4 (3)	N4—C20—C15	105.7 (2)
C6—C1—N1	108.6 (3)	C19—C20—C15	121.9 (3)
C1—C2—C3	116.2 (3)	N3—C21—N4	111.0 (3)
C4—C3—C2	122.2 (3)	N3—C21—C22	126.7 (3)
C5—C4—C3	121.5 (3)	N4—C21—C22	122.3 (3)
C4—C5—C6	116.6 (3)	C21—C22—C23	114.2 (2)
N2—C6—C5	132.4 (3)	C24—C23—C28	118.4 (3)
N2—C6—C1	105.1 (2)	C24—C23—C22	119.2 (3)
C5—C6—C1	122.5 (3)	C28—C23—C22	122.3 (3)
N1—C7—N2	111.1 (3)	C23—C24—C25	121.0 (4)
N1—C7—C8	125.7 (3)	C26—C25—C24	120.3 (4)
N2—C7—C8	123.2 (3)	C27—C26—C25	119.2 (3)
C7—C8—C9	115.3 (2)	C26—C27—C28	121.0 (4)
C14—C9—C10	118.7 (3)	C23—C28—C27	120.0 (3)
N3—Zn1—N1—C7	−127.2 (2)	C9—C10—C11—C12	−0.7 (5)
Cl1—Zn1—N1—C7	108.4 (2)	C10—C11—C12—C13	0.1 (6)
Cl2—Zn1—N1—C7	−10.3 (3)	C11—C12—C13—C14	0.2 (7)
N3—Zn1—N1—C1	71.1 (2)	C10—C9—C14—C13	−0.8 (6)
Cl1—Zn1—N1—C1	−53.4 (2)	C8—C9—C14—C13	177.8 (4)
Cl2—Zn1—N1—C1	−172.09 (18)	C12—C13—C14—C9	0.2 (7)
N1—Zn1—N3—C21	−124.5 (2)	C21—N3—C15—C16	−178.9 (3)
Cl1—Zn1—N3—C21	−8.3 (3)	Zn1—N3—C15—C16	−9.6 (4)
Cl2—Zn1—N3—C21	111.9 (2)	C21—N3—C15—C20	0.4 (3)
N1—Zn1—N3—C15	69.1 (2)	Zn1—N3—C15—C20	169.74 (18)
Cl1—Zn1—N3—C15	−174.72 (17)	C20—C15—C16—C17	1.3 (4)
Cl2—Zn1—N3—C15	−54.5 (2)	N3—C15—C16—C17	−179.4 (3)
C7—N1—C1—C2	−178.7 (3)	C15—C16—C17—C18	0.2 (5)
Zn1—N1—C1—C2	−13.0 (4)	C16—C17—C18—C19	−1.3 (5)
C7—N1—C1—C6	−0.3 (3)	C17—C18—C19—C20	0.8 (5)
Zn1—N1—C1—C6	165.41 (18)	C21—N4—C20—C19	−178.7 (3)
C6—C1—C2—C3	0.7 (4)	C21—N4—C20—C15	0.7 (3)
N1—C1—C2—C3	178.9 (3)	C18—C19—C20—N4	−180.0 (3)
C1—C2—C3—C4	−0.3 (5)	C18—C19—C20—C15	0.7 (4)
C2—C3—C4—C5	−0.2 (5)	C16—C15—C20—N4	178.7 (3)
C3—C4—C5—C6	0.3 (5)	N3—C15—C20—N4	−0.7 (3)
C7—N2—C6—C5	179.0 (3)	C16—C15—C20—C19	−1.8 (4)
C7—N2—C6—C1	−0.8 (3)	N3—C15—C20—C19	178.8 (3)
C4—C5—C6—N2	−179.7 (3)	C15—N3—C21—N4	0.0 (3)
C4—C5—C6—C1	0.0 (4)	Zn1—N3—C21—N4	−167.94 (18)
C2—C1—C6—N2	179.2 (3)	C15—N3—C21—C22	−177.5 (3)
N1—C1—C6—N2	0.7 (3)	Zn1—N3—C21—C22	14.5 (4)
C2—C1—C6—C5	−0.6 (4)	C20—N4—C21—N3	−0.5 (3)
N1—C1—C6—C5	−179.1 (3)	C20—N4—C21—C22	177.2 (2)
C1—N1—C7—N2	−0.2 (3)	N3—C21—C22—C23	86.8 (4)
Zn1—N1—C7—N2	−164.03 (18)	N4—C21—C22—C23	−90.6 (3)
C1—N1—C7—C8	180.0 (3)	C21—C22—C23—C24	−151.6 (3)
Zn1—N1—C7—C8	16.1 (4)	C21—C22—C23—C28	29.1 (4)
C6—N2—C7—N1	0.6 (3)	C28—C23—C24—C25	0.5 (5)
C6—N2—C7—C8	−179.5 (2)	C22—C23—C24—C25	−178.9 (3)
N1—C7—C8—C9	81.8 (4)	C23—C24—C25—C26	0.6 (6)
N2—C7—C8—C9	−98.0 (3)	C24—C25—C26—C27	−1.2 (6)
C7—C8—C9—C14	30.9 (5)	C25—C26—C27—C28	0.7 (7)
C7—C8—C9—C10	−150.5 (3)	C24—C23—C28—C27	−0.9 (6)
C14—C9—C10—C11	1.0 (5)	C22—C23—C28—C27	178.4 (3)
C8—C9—C10—C11	−177.7 (3)	C26—C27—C28—C23	0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2^i	0.86	2.46	3.240 (3)	152
N4—H4A···Cl1^ii	0.86	2.55	3.314 (3)	148
C8—H8A···Cl2	0.97	2.81	3.594 (3)	138

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.