[1,2-Bis(1H-benzimidazol-2-yl-κN ³)ethane]dichloridozinc(II)

Abstract

The title compound, [ZnCl₂(C₁₆H₁₄N₄)], crystallizes with two mol­ecules in the asymmetric unit. The Zn^II atoms show distorted tetrahedral coordination environments. Adjacent mol­ecules are linked by N—H⋯Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis of the ligand, see: van Albada et al. (1995 ▶). For the zinc dichloride adduct of a similar N-heterocycle, see: Zhou et al. (2010 ▶).

Experimental

Crystal data

• [ZnCl₂(C₁₆H₁₄N₄)]

• M _r = 398.58

• Monoclinic,

• a = 8.0868 (4) Å

• b = 13.8605 (8) Å

• c = 14.8504 (8) Å

• β = 92.664 (1)°

• V = 1662.7 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 1.80 mm⁻¹

• T = 293 K

• 0.48 × 0.34 × 0.30 mm

Data collection

• Bruker SMART diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.479, T _max = 0.614

• 8555 measured reflections

• 5820 independent reflections

• 4956 reflections with I > 2σ(I)

• R _int = 0.018

Refinement

• R[F ² > 2σ(F ²)] = 0.029

• wR(F ²) = 0.077

• S = 0.97

• 5820 reflections

• 415 parameters

• 1 restraint

• H-atom parameters constrained

• Δρ_max = 0.30 e Å⁻³

• Δρ_min = −0.30 e Å⁻³

• Absolute structure: Flack (1983 ▶), 2049 Friedel pairs

• Flack parameter: 0.1 (1)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl3	0.86	2.64	3.316 (3)	137
N3—H3⋯Cl4i	0.86	2.76	3.291 (3)	121
N6—H6⋯Cl1ii	0.86	2.39	3.225 (3)	164
N7—H7⋯Cl2iii	0.86	2.52	3.277 (3)	148

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Experimental

1,4-Bis(2-benzimidazolyl)ethanebutane was synthesized by using a literature method (van Albada et al., 1995). To a solution of zinc chloride hexahydrate (0.25 g, 1 mmol) in ethanol (3 ml) was added an aqueous solution (4 ml) of the ligand (0.24 g, 1 mmol). The reactants were sealed in a 15-ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 413 K for 3 days. The cool solution yielded single crystals in ca 30% yield.

Refinement

Hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.95–0.99 Å; N–H 0.88 Å U_iso(H) = 1.2U_eq(C, N)].

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of ZnCl2(C16H14N4) at the 50% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.

Crystal data

[ZnCl2(C16H14N4)]	F(000) = 808
Mr = 398.58	Dx = 1.592 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4769 reflections
a = 8.0868 (4) Å	θ = 2.5–27.1°
b = 13.8605 (8) Å	µ = 1.80 mm−1
c = 14.8504 (8) Å	T = 293 K
β = 92.664 (1)°	Block, colorless
V = 1662.7 (2) Å3	0.48 × 0.34 × 0.30 mm
Z = 4

Data collection

Bruker SMART diffractometer	5820 independent reflections
Radiation source: fine-focus sealed tube	4956 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.479, Tmax = 0.614	k = −17→13
8555 measured reflections	l = −18→15

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0406P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.002
5820 reflections	Δρmax = 0.30 e Å−3
415 parameters	Δρmin = −0.30 e Å−3
1 restraint	Absolute structure: Flack (1983), 2049 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.1 (1)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.24147 (5)	0.50006 (3)	0.64876 (2)	0.03664 (11)
Zn2	0.19950 (5)	0.65365 (3)	1.15403 (2)	0.03913 (11)
Cl1	−0.01667 (11)	0.50457 (12)	0.58667 (6)	0.0633 (3)
Cl2	0.43158 (10)	0.50750 (9)	0.54292 (5)	0.0475 (2)
Cl3	0.42290 (13)	0.60363 (9)	1.08123 (6)	0.0558 (3)
Cl4	−0.01188 (12)	0.67049 (9)	1.05101 (6)	0.0528 (3)
N1	0.2783 (4)	0.6025 (2)	0.74082 (19)	0.0409 (7)
N2	0.2933 (4)	0.6691 (3)	0.8750 (2)	0.0508 (8)
H2	0.2833	0.6764	0.9320	0.061*
N3	0.2869 (4)	0.2549 (2)	0.8128 (2)	0.0447 (8)
H3	0.2932	0.2255	0.8638	0.054*
N4	0.2675 (4)	0.3733 (2)	0.71535 (18)	0.0362 (7)
N5	0.1409 (4)	0.5614 (3)	1.25109 (18)	0.0425 (8)
N6	0.0915 (4)	0.4941 (3)	1.38061 (18)	0.0450 (7)
H6	0.0781	0.4883	1.4375	0.054*
N7	0.3232 (4)	0.8927 (3)	1.3116 (2)	0.0423 (8)
H7	0.3505	0.9194	1.3623	0.051*
N8	0.2503 (4)	0.7799 (2)	1.21321 (19)	0.0393 (7)
C1	0.3522 (5)	0.6924 (3)	0.7341 (2)	0.0412 (9)
C2	0.4079 (5)	0.7424 (3)	0.6600 (3)	0.0556 (11)
H2A	0.4011	0.7154	0.6026	0.067*
C3	0.4724 (6)	0.8320 (4)	0.6743 (3)	0.0649 (13)
H3A	0.5124	0.8660	0.6259	0.078*
C4	0.4803 (6)	0.8741 (4)	0.7593 (4)	0.0697 (13)
H4	0.5237	0.9359	0.7662	0.084*
C5	0.4259 (6)	0.8269 (4)	0.8327 (3)	0.0627 (12)
H5	0.4321	0.8550	0.8897	0.075*
C6	0.3612 (5)	0.7356 (3)	0.8188 (3)	0.0465 (10)
C7	0.2453 (4)	0.5917 (3)	0.8278 (2)	0.0393 (8)
C8	0.1625 (5)	0.5068 (3)	0.8669 (2)	0.0474 (9)
H8A	0.0683	0.4893	0.8275	0.057*
H8B	0.1204	0.5254	0.9245	0.057*
C9	0.2725 (5)	0.4180 (3)	0.8812 (2)	0.0467 (10)
H9A	0.3847	0.4394	0.8959	0.056*
H9B	0.2350	0.3824	0.9327	0.056*
C10	0.2755 (4)	0.3506 (3)	0.8020 (2)	0.0379 (8)
C11	0.2870 (5)	0.2110 (3)	0.7301 (3)	0.0419 (9)
C12	0.2914 (5)	0.1150 (3)	0.7039 (3)	0.0526 (11)
H12	0.2971	0.0652	0.7459	0.063*
C13	0.2871 (5)	0.0971 (3)	0.6128 (3)	0.0572 (12)
H13	0.2904	0.0336	0.5927	0.069*
C14	0.2778 (5)	0.1719 (3)	0.5497 (3)	0.0503 (11)
H14	0.2759	0.1569	0.4886	0.060*
C15	0.2714 (5)	0.2670 (3)	0.5756 (3)	0.0460 (10)
H15	0.2648	0.3165	0.5333	0.055*
C16	0.2752 (4)	0.2864 (3)	0.6687 (2)	0.0367 (8)
C17	0.1120 (5)	0.4632 (3)	1.2365 (3)	0.0449 (9)
C18	0.1112 (6)	0.4077 (4)	1.1586 (3)	0.0608 (12)
H18	0.1288	0.4354	1.1028	0.073*
C19	0.0837 (6)	0.3114 (4)	1.1666 (4)	0.0710 (14)
H19	0.0832	0.2729	1.1153	0.085*
C20	0.0565 (6)	0.2690 (4)	1.2494 (3)	0.0703 (14)
H20	0.0409	0.2026	1.2522	0.084*
C21	0.0520 (5)	0.3218 (4)	1.3262 (3)	0.0625 (12)
H21	0.0306	0.2933	1.3812	0.075*
C22	0.0806 (5)	0.4199 (3)	1.3191 (3)	0.0464 (10)
C23	0.1259 (4)	0.5765 (3)	1.3389 (2)	0.0383 (8)
C24	0.1397 (4)	0.6706 (3)	1.3870 (2)	0.0433 (9)
H24A	0.1299	0.6588	1.4509	0.052*
H24B	0.0469	0.7107	1.3669	0.052*
C25	0.3010 (5)	0.7277 (3)	1.3742 (2)	0.0432 (9)
H25A	0.3304	0.7617	1.4298	0.052*
H25B	0.3892	0.6824	1.3634	0.052*
C26	0.2912 (4)	0.7987 (3)	1.2992 (2)	0.0382 (8)
C27	0.3052 (4)	0.9398 (3)	1.2296 (3)	0.0420 (9)
C28	0.3225 (5)	1.0351 (3)	1.2046 (3)	0.0553 (11)
H28	0.3498	1.0827	1.2467	0.066*
C29	0.2976 (5)	1.0563 (3)	1.1143 (3)	0.0596 (12)
H29	0.3090	1.1197	1.0949	0.071*
C30	0.2561 (5)	0.9853 (4)	1.0518 (3)	0.0579 (12)
H30	0.2421	1.0023	0.9914	0.069*
C31	0.2346 (5)	0.8899 (3)	1.0759 (3)	0.0486 (10)
H31	0.2055	0.8429	1.0334	0.058*
C32	0.2591 (4)	0.8677 (3)	1.1681 (2)	0.0399 (9)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Zn1	0.0431 (2)	0.0407 (2)	0.02621 (18)	0.0000 (2)	0.00288 (14)	0.00228 (18)
Zn2	0.0505 (2)	0.0409 (3)	0.02615 (18)	0.0009 (2)	0.00373 (15)	−0.00242 (18)
Cl1	0.0401 (5)	0.1098 (10)	0.0401 (5)	0.0026 (6)	0.0018 (4)	0.0161 (6)
Cl2	0.0464 (5)	0.0616 (6)	0.0353 (4)	−0.0007 (5)	0.0111 (3)	0.0066 (5)
Cl3	0.0548 (6)	0.0724 (8)	0.0410 (5)	0.0098 (5)	0.0106 (4)	−0.0068 (5)
Cl4	0.0539 (5)	0.0680 (8)	0.0358 (4)	0.0051 (5)	−0.0055 (4)	−0.0060 (5)
N1	0.0497 (18)	0.0401 (19)	0.0331 (15)	0.0015 (15)	0.0033 (13)	0.0006 (14)
N2	0.072 (2)	0.045 (2)	0.0350 (15)	−0.0021 (18)	0.0042 (14)	−0.0078 (15)
N3	0.058 (2)	0.040 (2)	0.0361 (17)	−0.0006 (16)	0.0062 (14)	0.0112 (15)
N4	0.0413 (16)	0.0388 (19)	0.0288 (15)	−0.0049 (14)	0.0043 (12)	0.0018 (13)
N5	0.0490 (18)	0.049 (2)	0.0300 (15)	−0.0036 (16)	0.0049 (13)	0.0002 (14)
N6	0.0483 (16)	0.058 (2)	0.0292 (14)	−0.0059 (18)	0.0031 (12)	0.0082 (16)
N7	0.0390 (16)	0.049 (2)	0.0384 (17)	0.0026 (15)	0.0006 (13)	−0.0096 (15)
N8	0.0461 (17)	0.039 (2)	0.0321 (16)	−0.0003 (14)	−0.0001 (13)	−0.0041 (14)
C1	0.044 (2)	0.039 (2)	0.0410 (19)	0.0053 (17)	0.0052 (16)	0.0032 (17)
C2	0.067 (3)	0.048 (3)	0.052 (2)	0.000 (2)	0.009 (2)	0.007 (2)
C3	0.063 (3)	0.051 (3)	0.082 (3)	0.002 (2)	0.015 (2)	0.020 (3)
C4	0.060 (3)	0.047 (3)	0.102 (4)	−0.005 (2)	0.000 (3)	−0.002 (3)
C5	0.074 (3)	0.047 (3)	0.067 (3)	−0.005 (2)	0.002 (2)	−0.011 (2)
C6	0.051 (2)	0.043 (2)	0.045 (2)	0.0038 (19)	0.0014 (18)	−0.0025 (18)
C7	0.042 (2)	0.041 (2)	0.0351 (18)	0.0051 (17)	0.0059 (15)	−0.0006 (16)
C8	0.057 (2)	0.051 (2)	0.0359 (17)	0.000 (2)	0.0175 (15)	−0.007 (2)
C9	0.065 (3)	0.050 (3)	0.0254 (18)	−0.007 (2)	0.0020 (16)	0.0026 (18)
C10	0.0391 (19)	0.041 (2)	0.0342 (19)	−0.0046 (17)	0.0063 (14)	0.0036 (17)
C11	0.038 (2)	0.040 (2)	0.047 (2)	0.0009 (17)	0.0056 (16)	0.0019 (18)
C12	0.056 (2)	0.041 (3)	0.061 (3)	−0.002 (2)	0.011 (2)	0.001 (2)
C13	0.048 (2)	0.043 (3)	0.082 (3)	−0.002 (2)	0.010 (2)	−0.014 (2)
C14	0.044 (2)	0.055 (3)	0.052 (2)	0.001 (2)	0.0078 (17)	−0.017 (2)
C15	0.044 (2)	0.054 (3)	0.040 (2)	−0.0032 (19)	0.0024 (17)	−0.0066 (19)
C16	0.0302 (17)	0.042 (2)	0.0384 (19)	−0.0021 (16)	0.0029 (14)	−0.0009 (17)
C17	0.045 (2)	0.047 (2)	0.042 (2)	−0.0060 (18)	−0.0013 (16)	−0.0003 (17)
C18	0.074 (3)	0.062 (3)	0.046 (2)	−0.007 (3)	0.002 (2)	−0.006 (2)
C19	0.078 (3)	0.063 (4)	0.072 (3)	−0.016 (3)	0.005 (3)	−0.019 (3)
C20	0.067 (3)	0.052 (3)	0.091 (4)	−0.011 (2)	−0.002 (3)	−0.007 (3)
C21	0.056 (3)	0.062 (3)	0.069 (3)	−0.010 (2)	0.000 (2)	0.017 (3)
C22	0.039 (2)	0.054 (3)	0.046 (2)	−0.0055 (19)	−0.0032 (16)	0.000 (2)
C23	0.0337 (18)	0.051 (2)	0.0306 (18)	0.0035 (17)	0.0015 (14)	0.0039 (16)
C24	0.0468 (19)	0.057 (3)	0.0269 (16)	0.0026 (19)	0.0077 (14)	−0.0013 (17)
C25	0.045 (2)	0.053 (3)	0.0311 (18)	−0.0007 (18)	−0.0024 (15)	−0.0045 (18)
C26	0.0343 (18)	0.043 (2)	0.038 (2)	0.0007 (16)	0.0065 (15)	−0.0086 (17)
C27	0.035 (2)	0.043 (3)	0.048 (2)	0.0037 (17)	0.0050 (16)	−0.0049 (19)
C28	0.048 (2)	0.039 (3)	0.078 (3)	−0.0045 (19)	−0.004 (2)	−0.006 (2)
C29	0.054 (3)	0.039 (3)	0.085 (3)	0.001 (2)	0.008 (2)	0.014 (3)
C30	0.057 (2)	0.053 (3)	0.064 (3)	0.007 (2)	0.003 (2)	0.017 (2)
C31	0.050 (2)	0.051 (3)	0.044 (2)	−0.001 (2)	0.0029 (17)	0.0048 (19)
C32	0.0368 (19)	0.037 (2)	0.046 (2)	0.0034 (17)	0.0072 (16)	−0.0038 (18)

Geometric parameters (Å, °)

Zn1—N1	1.984 (3)	C8—H8B	0.9700
Zn1—N4	2.023 (3)	C9—C10	1.503 (5)
Zn1—Cl1	2.243 (1)	C9—H9A	0.9700
Zn1—Cl2	2.252 (1)	C9—H9B	0.9700
Zn2—N5	2.000 (3)	C11—C12	1.386 (6)
Zn2—N8	1.992 (3)	C11—C16	1.387 (5)
Zn2—Cl3	2.257 (1)	C12—C13	1.374 (6)
Zn2—Cl4	2.253 (1)	C12—H12	0.9300
N1—C7	1.339 (4)	C13—C14	1.397 (6)
N1—C1	1.388 (5)	C13—H13	0.9300
N2—C7	1.330 (5)	C14—C15	1.375 (6)
N2—C6	1.375 (5)	C14—H14	0.9300
N2—H2	0.8600	C15—C16	1.409 (5)
N3—C10	1.339 (5)	C15—H15	0.9300
N3—C11	1.370 (5)	C17—C18	1.390 (6)
N3—H3	0.8600	C17—C22	1.399 (6)
N4—C10	1.323 (4)	C18—C19	1.358 (7)
N4—C16	1.392 (5)	C18—H18	0.9300
N5—C23	1.332 (4)	C19—C20	1.390 (7)
N5—C17	1.397 (5)	C19—H19	0.9300
N6—C23	1.334 (5)	C20—C21	1.357 (7)
N6—C22	1.375 (5)	C20—H20	0.9300
N6—H6	0.8600	C21—C22	1.385 (6)
N7—C26	1.338 (5)	C21—H21	0.9300
N7—C27	1.384 (5)	C23—C24	1.489 (6)
N7—H7	0.8600	C24—C25	1.545 (5)
N8—C26	1.331 (4)	C24—H24A	0.9700
N8—C32	1.392 (5)	C24—H24B	0.9700
C1—C6	1.392 (5)	C25—C26	1.486 (6)
C1—C2	1.393 (5)	C25—H25A	0.9700
C2—C3	1.359 (7)	C25—H25B	0.9700
C2—H2A	0.9300	C27—C28	1.380 (6)
C3—C4	1.390 (7)	C27—C32	1.393 (5)
C3—H3A	0.9300	C28—C29	1.378 (6)
C4—C5	1.361 (7)	C28—H28	0.9300
C4—H4	0.9300	C29—C30	1.383 (7)
C5—C6	1.382 (6)	C29—H29	0.9300
C5—H5	0.9300	C30—C31	1.382 (6)
C7—C8	1.485 (6)	C30—H30	0.9300
C8—C9	1.527 (6)	C31—C32	1.408 (5)
C8—H8A	0.9700	C31—H31	0.9300
N1—Zn1—N4	106.03 (12)	N3—C11—C12	132.8 (4)
N1—Zn1—Cl1	111.74 (10)	N3—C11—C16	104.5 (3)
N4—Zn1—Cl1	107.38 (9)	C12—C11—C16	122.7 (4)
N1—Zn1—Cl2	111.27 (10)	C13—C12—C11	116.7 (4)
N4—Zn1—Cl2	108.80 (9)	C13—C12—H12	121.6
Cl1—Zn1—Cl2	111.37 (3)	C11—C12—H12	121.6
N8—Zn2—N5	107.11 (12)	C12—C13—C14	121.6 (4)
N8—Zn2—Cl4	110.05 (9)	C12—C13—H13	119.2
N5—Zn2—Cl4	110.98 (10)	C14—C13—H13	119.2
N8—Zn2—Cl3	109.15 (9)	C15—C14—C13	121.7 (4)
N5—Zn2—Cl3	111.76 (10)	C15—C14—H14	119.1
Cl4—Zn2—Cl3	107.79 (4)	C13—C14—H14	119.1
C7—N1—C1	106.0 (3)	C14—C15—C16	117.2 (4)
C7—N1—Zn1	123.7 (3)	C14—C15—H15	121.4
C1—N1—Zn1	130.1 (2)	C16—C15—H15	121.4
C7—N2—C6	109.6 (3)	C11—C16—N4	109.2 (3)
C7—N2—H2	125.2	C11—C16—C15	120.0 (4)
C6—N2—H2	125.2	N4—C16—C15	130.8 (4)
C10—N3—C11	109.7 (3)	C18—C17—N5	131.6 (4)
C10—N3—H3	125.2	C18—C17—C22	119.9 (4)
C11—N3—H3	125.2	N5—C17—C22	108.5 (4)
C10—N4—C16	106.1 (3)	C19—C18—C17	117.7 (5)
C10—N4—Zn1	132.9 (3)	C19—C18—H18	121.1
C16—N4—Zn1	121.0 (2)	C17—C18—H18	121.1
C23—N5—C17	106.4 (3)	C18—C19—C20	121.8 (5)
C23—N5—Zn2	129.9 (3)	C18—C19—H19	119.1
C17—N5—Zn2	123.7 (3)	C20—C19—H19	119.1
C23—N6—C22	109.9 (3)	C21—C20—C19	121.9 (5)
C23—N6—H6	125.1	C21—C20—H20	119.1
C22—N6—H6	125.1	C19—C20—H20	119.1
C26—N7—C27	109.1 (3)	C20—C21—C22	117.0 (5)
C26—N7—H7	125.5	C20—C21—H21	121.5
C27—N7—H7	125.5	C22—C21—H21	121.5
C26—N8—C32	105.9 (3)	N6—C22—C21	133.6 (4)
C26—N8—Zn2	129.3 (3)	N6—C22—C17	104.7 (4)
C32—N8—Zn2	124.7 (2)	C21—C22—C17	121.7 (4)
N1—C1—C6	109.0 (3)	N5—C23—N6	110.5 (4)
N1—C1—C2	131.2 (4)	N5—C23—C24	126.8 (4)
C6—C1—C2	119.7 (4)	N6—C23—C24	122.7 (3)
C3—C2—C1	117.8 (4)	C23—C24—C25	115.8 (3)
C3—C2—H2A	121.1	C23—C24—H24A	108.3
C1—C2—H2A	121.1	C25—C24—H24A	108.3
C2—C3—C4	121.8 (4)	C23—C24—H24B	108.3
C2—C3—H3A	119.1	C25—C24—H24B	108.3
C4—C3—H3A	119.1	H24A—C24—H24B	107.4
C5—C4—C3	121.6 (5)	C26—C25—C24	114.6 (3)
C5—C4—H4	119.2	C26—C25—H25A	108.6
C3—C4—H4	119.2	C24—C25—H25A	108.6
C4—C5—C6	117.0 (4)	C26—C25—H25B	108.6
C4—C5—H5	121.5	C24—C25—H25B	108.6
C6—C5—H5	121.5	H25A—C25—H25B	107.6
N2—C6—C5	133.0 (4)	N8—C26—N7	111.1 (4)
N2—C6—C1	104.8 (4)	N8—C26—C25	126.3 (4)
C5—C6—C1	122.2 (4)	N7—C26—C25	122.6 (3)
N2—C7—N1	110.6 (4)	C28—C27—N7	132.9 (4)
N2—C7—C8	123.9 (3)	C28—C27—C32	122.5 (4)
N1—C7—C8	125.4 (3)	N7—C27—C32	104.6 (4)
C7—C8—C9	115.0 (3)	C29—C28—C27	117.0 (4)
C7—C8—H8A	108.5	C29—C28—H28	121.5
C9—C8—H8A	108.5	C27—C28—H28	121.5
C7—C8—H8B	108.5	C28—C29—C30	121.3 (4)
C9—C8—H8B	108.5	C28—C29—H29	119.3
H8A—C8—H8B	107.5	C30—C29—H29	119.3
C10—C9—C8	115.0 (3)	C31—C30—C29	122.5 (4)
C10—C9—H9A	108.5	C31—C30—H30	118.8
C8—C9—H9A	108.5	C29—C30—H30	118.8
C10—C9—H9B	108.5	C30—C31—C32	116.6 (4)
C8—C9—H9B	108.5	C30—C31—H31	121.7
H9A—C9—H9B	107.5	C32—C31—H31	121.7
N4—C10—N3	110.6 (3)	N8—C32—C27	109.2 (3)
N4—C10—C9	127.7 (4)	N8—C32—C31	130.6 (4)
N3—C10—C9	121.7 (3)	C27—C32—C31	120.1 (4)
N4—Zn1—N1—C7	−28.8 (3)	C12—C13—C14—C15	−0.5 (6)
Cl1—Zn1—N1—C7	87.8 (3)	C13—C14—C15—C16	0.2 (6)
Cl2—Zn1—N1—C7	−147.0 (3)	N3—C11—C16—N4	−0.3 (4)
N4—Zn1—N1—C1	145.0 (3)	C12—C11—C16—N4	177.9 (4)
Cl1—Zn1—N1—C1	−98.3 (3)	N3—C11—C16—C15	−179.8 (3)
Cl2—Zn1—N1—C1	26.9 (3)	C12—C11—C16—C15	−1.6 (6)
N1—Zn1—N4—C10	12.5 (3)	C10—N4—C16—C11	0.4 (4)
Cl1—Zn1—N4—C10	−107.1 (3)	Zn1—N4—C16—C11	−177.9 (2)
Cl2—Zn1—N4—C10	132.2 (3)	C10—N4—C16—C15	179.8 (4)
N1—Zn1—N4—C16	−169.8 (3)	Zn1—N4—C16—C15	1.5 (5)
Cl1—Zn1—N4—C16	70.6 (3)	C14—C15—C16—C11	0.7 (5)
Cl2—Zn1—N4—C16	−50.0 (3)	C14—C15—C16—N4	−178.6 (3)
N8—Zn2—N5—C23	3.8 (4)	C23—N5—C17—C18	179.8 (4)
Cl4—Zn2—N5—C23	−116.4 (3)	Zn2—N5—C17—C18	−1.8 (6)
Cl3—Zn2—N5—C23	123.3 (3)	C23—N5—C17—C22	−0.6 (4)
N8—Zn2—N5—C17	−174.1 (3)	Zn2—N5—C17—C22	177.8 (2)
Cl4—Zn2—N5—C17	65.7 (3)	N5—C17—C18—C19	177.8 (5)
Cl3—Zn2—N5—C17	−54.6 (3)	C22—C17—C18—C19	−1.8 (7)
N5—Zn2—N8—C26	19.8 (3)	C17—C18—C19—C20	0.3 (8)
Cl4—Zn2—N8—C26	140.6 (3)	C18—C19—C20—C21	1.6 (8)
Cl3—Zn2—N8—C26	−101.3 (3)	C19—C20—C21—C22	−1.8 (7)
N5—Zn2—N8—C32	−164.5 (3)	C23—N6—C22—C21	178.4 (4)
Cl4—Zn2—N8—C32	−43.7 (3)	C23—N6—C22—C17	0.3 (4)
Cl3—Zn2—N8—C32	74.4 (3)	C20—C21—C22—N6	−177.4 (4)
C7—N1—C1—C6	−0.6 (4)	C20—C21—C22—C17	0.3 (6)
Zn1—N1—C1—C6	−175.3 (3)	C18—C17—C22—N6	179.8 (4)
C7—N1—C1—C2	−178.0 (4)	N5—C17—C22—N6	0.1 (4)
Zn1—N1—C1—C2	7.3 (6)	C18—C17—C22—C21	1.5 (6)
N1—C1—C2—C3	178.4 (4)	N5—C17—C22—C21	−178.2 (4)
C6—C1—C2—C3	1.2 (6)	C17—N5—C23—N6	0.8 (4)
C1—C2—C3—C4	−1.3 (7)	Zn2—N5—C23—N6	−177.4 (3)
C2—C3—C4—C5	1.0 (8)	C17—N5—C23—C24	−177.7 (4)
C3—C4—C5—C6	−0.5 (7)	Zn2—N5—C23—C24	4.1 (5)
C7—N2—C6—C5	178.6 (5)	C22—N6—C23—N5	−0.7 (4)
C7—N2—C6—C1	−0.5 (4)	C22—N6—C23—C24	177.9 (3)
C4—C5—C6—N2	−178.5 (5)	N5—C23—C24—C25	−54.7 (5)
C4—C5—C6—C1	0.4 (7)	N6—C23—C24—C25	127.0 (4)
N1—C1—C6—N2	0.7 (4)	C23—C24—C25—C26	92.8 (4)
C2—C1—C6—N2	178.4 (4)	C32—N8—C26—N7	0.8 (4)
N1—C1—C6—C5	−178.6 (4)	Zn2—N8—C26—N7	177.1 (2)
C2—C1—C6—C5	−0.8 (6)	C32—N8—C26—C25	−179.5 (3)
C6—N2—C7—N1	0.2 (5)	Zn2—N8—C26—C25	−3.2 (5)
C6—N2—C7—C8	−178.3 (4)	C27—N7—C26—N8	−0.8 (4)
C1—N1—C7—N2	0.2 (4)	C27—N7—C26—C25	179.5 (3)
Zn1—N1—C7—N2	175.4 (2)	C24—C25—C26—N8	−56.7 (5)
C1—N1—C7—C8	178.7 (4)	C24—C25—C26—N7	123.0 (4)
Zn1—N1—C7—C8	−6.2 (5)	C26—N7—C27—C28	179.8 (4)
N2—C7—C8—C9	−104.4 (4)	C26—N7—C27—C32	0.5 (4)
N1—C7—C8—C9	77.3 (5)	N7—C27—C28—C29	178.7 (4)
C7—C8—C9—C10	−88.8 (4)	C32—C27—C28—C29	−2.1 (6)
C16—N4—C10—N3	−0.3 (4)	C27—C28—C29—C30	0.4 (6)
Zn1—N4—C10—N3	177.6 (2)	C28—C29—C30—C31	1.0 (7)
C16—N4—C10—C9	179.9 (4)	C29—C30—C31—C32	−0.7 (6)
Zn1—N4—C10—C9	−2.2 (6)	C26—N8—C32—C27	−0.5 (4)
C11—N3—C10—N4	0.2 (4)	Zn2—N8—C32—C27	−177.0 (2)
C11—N3—C10—C9	180.0 (3)	C26—N8—C32—C31	177.4 (4)
C8—C9—C10—N4	35.1 (6)	Zn2—N8—C32—C31	0.9 (6)
C8—C9—C10—N3	−144.7 (4)	C28—C27—C32—N8	−179.4 (4)
C10—N3—C11—C12	−177.8 (4)	N7—C27—C32—N8	0.0 (4)
C10—N3—C11—C16	0.1 (4)	C28—C27—C32—C31	2.5 (6)
N3—C11—C12—C13	178.9 (4)	N7—C27—C32—C31	−178.1 (3)
C16—C11—C12—C13	1.3 (6)	C30—C31—C32—N8	−178.7 (4)
C11—C12—C13—C14	−0.3 (6)	C30—C31—C32—C27	−1.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl3	0.86	2.64	3.316 (3)	137
N3—H3···Cl4i	0.86	2.76	3.291 (3)	121
N6—H6···Cl1ii	0.86	2.39	3.225 (3)	164
N7—H7···Cl2iii	0.86	2.52	3.277 (3)	148

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