[1,2-Bis(1H-benzimidazol-2-yl-κN³)ethane]dichloridozinc(II)

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.029
• wR factor = 0.077
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop           1
PLAT152_ALERT_1_B The Supplied and Calc. Volume s.u. Differ by ...         -5 Units

Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         20
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................      58.51 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C16 H14 Cl2 N4 Zn
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         21

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.08
           From the CIF: _reflns_number_total               5820
           Count of symmetry unique reflns         3812
           Completeness (_total/calc)            152.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2008
           Fraction of Friedel pairs measured     0.527
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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).

S1. 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.

S2. 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)].

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

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.

[1,2-Bis(1H-benzimidazol-2-yl-κN³)ethane]dichloridozinc(II)

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) Å^3	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 monochromator	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 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)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0406P)^2] where P = (Fo^2 + 2Fc^2)/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	Absolute structure 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)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

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, º)

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···Cl4^i	0.86	2.76	3.291 (3)	121
N6—H6···Cl1^ii	0.86	2.39	3.225 (3)	164
N7—H7···Cl2^iii	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.