Bis(μ-3,5-dimethyl-4H-1,2,4-triazol-4-amine-κN:N)bis-[bis-(thio-cyanato-κN)zinc]-bis-(3,5-dimethyl-4H-1,2,4-triazol-4-amine-κN)bis-(thio-cyanato-κN)zinc (1/2).

In the crystal structure of the title 1:2 adduct, [Zn(2)(NCS)(4)(C(4)H(8)N(4))(2)]·2[Zn(NCS)(2)(C(4)H(8)N(4))(2)] or (Ia)·2(Ib), each Zn(II) atom is coordinated in a distorted tetra-hedral geometry by four N atoms from two triazole rings of two 4-amino-3,5-dimethyl-1,2,4-triazole (admt) ligands and two NCS(-) ligands. In (Ia), double N(1):N(2)-bridging admt ligands connect two Zn(II) atoms, forming a dimer with a Zn(2)(admt)(2) six-membered metallacycle located on a crystallographic inversion center. In (Ib), the admt ligands exhibit monodentate N(1)-coordination modes. Weak N-H⋯N, N-H⋯S and C-H⋯S hydrogen bonds play an important role in the inter-molecular packing. The S and C atoms of two thiocyanato ligands are disordered over two sets of sites in ratios of 0.57 (3):0.43 (3) and 0.63 (3):0.37 (3), respectively.

Related literature

For background to transition metal complexes of 1,2,4-triazole derivatives, see: Haasnoot (2000 ▶); Liu et al. (1999 ▶, 2003 ▶); Zhao et al. (2002 ▶); Yi et al. (2004 ▶); Lavrenova et al. (1992 ▶); Zhang et al. (2007 ▶, 2011 ▶). For related structures, see: Lavrenova et al. (1992 ▶); Zhang et al. (2007 ▶, 2011 ▶).

Experimental

Crystal data

[Zn2(NCS)4(C4H8N4)2]·2[Zn(NCS)2(C4H8N4)2]

M = 1399.08

Triclinic,

a = 8.7665 (8) Å

b = 9.3100 (5) Å

c = 20.661 (3) Å

α = 92.560 (9)°

β = 95.926 (2)°

γ = 115.427 (6)°

V = 1507.3 (3) Å3

Z = 1

Mo Kα radiation

μ = 1.91 mm−1

T = 223 K

0.34 × 0.30 × 0.14 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.564, T max = 0.776

14831 measured reflections

5484 independent reflections

4550 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.090

S = 1.04

5484 reflections

387 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027887/zq2110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027887/zq2110Isup2.hkl

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

[Zn2(NCS)4(C4H8N4)2]·2[Zn(NCS)2(C4H8N4)2]	Z = 1
Mr = 1399.08	F(000) = 712
Triclinic, P1	Dx = 1.541 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 8.7665 (8) Å	Cell parameters from 5140 reflections
b = 9.3100 (5) Å	θ = 3.1–25.4°
c = 20.661 (3) Å	µ = 1.91 mm−1
α = 92.560 (9)°	T = 223 K
β = 95.926 (2)°	Block, colourless
γ = 115.427 (6)°	0.34 × 0.30 × 0.14 mm
V = 1507.3 (3) Å3

Rigaku Mercury CCD diffractometer	5484 independent reflections
Radiation source: fine-focus sealed tube	4550 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→11
Tmin = 0.564, Tmax = 0.776	l = −22→24
14831 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0309P)2 + 1.5778P] where P = (Fo2 + 2Fc2)/3
5484 reflections	(Δ/σ)max < 0.001
387 parameters	Δρmax = 0.55 e Å−3
30 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.41245 (5)	0.63167 (5)	0.031974 (19)	0.03212 (12)
Zn2	0.54622 (5)	0.17586 (5)	0.34171 (2)	0.03310 (12)
S1A	−0.0157 (7)	0.7863 (17)	0.0518 (4)	0.065 (2)	0.57 (3)
C5A	0.1191 (16)	0.7222 (15)	0.0350 (8)	0.0438 (11)	0.57 (3)
S1B	0.032 (2)	0.858 (2)	0.0278 (11)	0.087 (5)	0.43 (3)
C5B	0.143 (2)	0.7546 (19)	0.0296 (10)	0.0438 (11)	0.43 (3)
S3A	0.786 (2)	0.3793 (9)	0.5571 (3)	0.110 (3)	0.63 (3)
C15A	0.7285 (16)	0.3210 (15)	0.4808 (4)	0.0438 (11)	0.63 (3)
S3B	0.717 (2)	0.397 (2)	0.5555 (7)	0.111 (6)	0.37 (3)
C15B	0.690 (3)	0.329 (3)	0.4793 (7)	0.0438 (11)	0.37 (3)
S2	0.82933 (14)	0.97029 (14)	0.20364 (5)	0.0594 (3)
S4	0.80473 (14)	0.52143 (13)	0.18706 (6)	0.0549 (3)
N1	0.3658 (3)	0.4141 (3)	0.06001 (13)	0.0294 (6)
N2	0.4699 (3)	0.3396 (3)	0.04834 (13)	0.0318 (6)
N3	0.3122 (3)	0.2214 (3)	0.12156 (13)	0.0305 (6)
N4	0.2470 (4)	0.1121 (4)	0.16740 (15)	0.0408 (7)
N5	0.2201 (4)	0.6795 (4)	0.02509 (17)	0.0471 (8)
N6	0.5860 (4)	0.7776 (4)	0.10139 (16)	0.0439 (8)
N7	0.5476 (3)	−0.0370 (3)	0.33052 (14)	0.0323 (7)
N8	0.6787 (4)	−0.0591 (4)	0.36615 (14)	0.0384 (7)
N9	0.5265 (4)	−0.2668 (3)	0.29609 (14)	0.0329 (7)
N10	0.4718 (4)	−0.4100 (4)	0.25494 (17)	0.0421 (8)
N11	0.3205 (3)	0.1727 (3)	0.35209 (13)	0.0327 (7)
N12	0.2521 (4)	0.2503 (3)	0.31036 (13)	0.0343 (7)
N13	0.1194 (3)	0.1971 (3)	0.39608 (13)	0.0292 (6)
N14	0.0123 (4)	0.1907 (4)	0.44340 (15)	0.0401 (7)
N15	0.6844 (4)	0.2796 (4)	0.42611 (16)	0.0474 (8)
N16	0.6258 (4)	0.3019 (4)	0.27023 (16)	0.0446 (8)
C1	0.4354 (4)	0.2233 (4)	0.08645 (16)	0.0326 (8)
C2	0.2705 (4)	0.3398 (4)	0.10392 (15)	0.0286 (7)
C3	0.5138 (5)	0.1114 (4)	0.09104 (19)	0.0443 (9)
H3A	0.4279	0.0037	0.0764	0.066*
H3B	0.5608	0.1156	0.1361	0.066*
H3C	0.6041	0.1413	0.0637	0.066*
C4	0.1382 (5)	0.3744 (5)	0.12993 (18)	0.0405 (9)
H4C	0.1100	0.4433	0.1022	0.061*
H4D	0.1804	0.4274	0.1739	0.061*
H4E	0.0371	0.2752	0.1308	0.061*
C6	0.6884 (5)	0.8569 (4)	0.14333 (19)	0.0374 (8)
C7	0.6631 (5)	−0.1990 (4)	0.34402 (18)	0.0395 (9)
C8	0.4587 (4)	−0.1629 (4)	0.28850 (16)	0.0312 (8)
C9	0.7755 (6)	−0.2747 (6)	0.3658 (2)	0.0694 (14)
H9A	0.8615	−0.2061	0.4012	0.104*
H9B	0.8305	−0.2903	0.3295	0.104*
H9C	0.7079	−0.3773	0.3810	0.104*
C10	0.3097 (5)	−0.1893 (5)	0.2399 (2)	0.0510 (11)
H10C	0.2944	−0.0922	0.2395	0.077*
H10D	0.2083	−0.2753	0.2516	0.077*
H10E	0.3293	−0.2177	0.1968	0.077*
C11	0.1301 (4)	0.2624 (4)	0.33821 (16)	0.0286 (7)
C12	0.2390 (4)	0.1428 (4)	0.40368 (17)	0.0317 (8)
C13	0.0177 (5)	0.3329 (5)	0.31128 (17)	0.0406 (9)
H13A	0.0787	0.4160	0.2843	0.061*
H13B	−0.0168	0.3785	0.3469	0.061*
H13C	−0.0825	0.2505	0.2850	0.061*
C14	0.2714 (5)	0.0639 (5)	0.4602 (2)	0.0513 (11)
H14C	0.3331	0.0038	0.4482	0.077*
H14D	0.1638	−0.0082	0.4734	0.077*
H14E	0.3388	0.1440	0.4962	0.077*
C16	0.7019 (4)	0.3929 (4)	0.23544 (18)	0.0351 (8)
HW1	0.139 (3)	0.046 (4)	0.1524 (17)	0.042*
HW2	0.238 (5)	0.164 (4)	0.2027 (13)	0.042*
HW3	0.441 (5)	−0.481 (4)	0.2816 (15)	0.042*
HW4	0.558 (3)	−0.405 (4)	0.2359 (17)	0.042*
HW5	−0.091 (3)	0.127 (4)	0.4243 (17)	0.042*
HW6	0.036 (5)	0.290 (3)	0.4554 (18)	0.042*

	U11	U22	U33	U12	U13	U23
Zn1	0.0362 (2)	0.0312 (2)	0.0369 (2)	0.02067 (19)	0.01070 (18)	0.00640 (17)
Zn2	0.0314 (2)	0.0340 (2)	0.0403 (2)	0.01972 (19)	0.00779 (18)	0.00290 (18)
S1A	0.0510 (18)	0.081 (4)	0.077 (3)	0.047 (2)	−0.0059 (19)	−0.026 (3)
C5A	0.034 (3)	0.041 (2)	0.055 (2)	0.017 (2)	0.0000 (18)	−0.0045 (19)
S1B	0.078 (5)	0.085 (7)	0.111 (8)	0.067 (6)	−0.048 (6)	−0.056 (6)
C5B	0.034 (3)	0.041 (2)	0.055 (2)	0.017 (2)	0.0000 (18)	−0.0045 (19)
S3A	0.182 (8)	0.066 (2)	0.046 (2)	0.030 (4)	−0.021 (3)	−0.0143 (17)
C15A	0.034 (3)	0.041 (2)	0.055 (2)	0.017 (2)	0.0000 (18)	−0.0045 (19)
S3B	0.116 (7)	0.085 (7)	0.067 (5)	−0.018 (4)	0.038 (4)	−0.033 (4)
C15B	0.034 (3)	0.041 (2)	0.055 (2)	0.017 (2)	0.0000 (18)	−0.0045 (19)
S2	0.0541 (6)	0.0548 (7)	0.0472 (6)	0.0039 (5)	0.0093 (5)	−0.0087 (5)
S4	0.0566 (7)	0.0515 (6)	0.0570 (7)	0.0211 (5)	0.0149 (5)	0.0211 (5)
N1	0.0330 (15)	0.0278 (15)	0.0312 (15)	0.0160 (13)	0.0072 (12)	0.0035 (12)
N2	0.0374 (16)	0.0299 (15)	0.0337 (16)	0.0195 (13)	0.0074 (13)	0.0031 (13)
N3	0.0359 (16)	0.0276 (15)	0.0283 (15)	0.0133 (13)	0.0062 (13)	0.0065 (12)
N4	0.0488 (19)	0.0378 (18)	0.0341 (18)	0.0158 (16)	0.0101 (16)	0.0085 (14)
N5	0.0395 (18)	0.051 (2)	0.063 (2)	0.0297 (17)	0.0105 (16)	0.0110 (17)
N6	0.0486 (19)	0.0391 (18)	0.0459 (19)	0.0225 (16)	0.0027 (17)	−0.0032 (16)
N7	0.0350 (16)	0.0318 (16)	0.0379 (17)	0.0216 (14)	0.0051 (13)	0.0070 (13)
N8	0.0424 (17)	0.0438 (18)	0.0373 (17)	0.0281 (15)	0.0006 (14)	−0.0003 (14)
N9	0.0368 (16)	0.0293 (15)	0.0369 (16)	0.0184 (13)	0.0055 (14)	0.0043 (13)
N10	0.047 (2)	0.0292 (17)	0.054 (2)	0.0193 (16)	0.0073 (16)	0.0054 (15)
N11	0.0351 (16)	0.0395 (17)	0.0342 (16)	0.0253 (14)	0.0075 (13)	0.0078 (13)
N12	0.0366 (16)	0.0415 (17)	0.0335 (16)	0.0243 (14)	0.0082 (13)	0.0059 (13)
N13	0.0236 (14)	0.0370 (16)	0.0296 (15)	0.0140 (13)	0.0094 (12)	0.0067 (12)
N14	0.0337 (17)	0.052 (2)	0.0390 (18)	0.0202 (17)	0.0140 (14)	0.0058 (16)
N15	0.0370 (17)	0.054 (2)	0.052 (2)	0.0229 (16)	−0.0020 (16)	−0.0105 (17)
N16	0.0428 (18)	0.0456 (19)	0.053 (2)	0.0238 (16)	0.0151 (16)	0.0129 (17)
C1	0.040 (2)	0.0259 (17)	0.0331 (19)	0.0150 (16)	0.0073 (16)	0.0042 (15)
C2	0.0316 (18)	0.0267 (17)	0.0248 (17)	0.0108 (15)	0.0025 (14)	−0.0006 (14)
C3	0.064 (3)	0.038 (2)	0.044 (2)	0.032 (2)	0.017 (2)	0.0111 (17)
C4	0.042 (2)	0.046 (2)	0.041 (2)	0.0237 (18)	0.0148 (17)	0.0091 (17)
C6	0.043 (2)	0.0328 (19)	0.041 (2)	0.0175 (18)	0.0173 (19)	0.0079 (17)
C7	0.044 (2)	0.042 (2)	0.040 (2)	0.0264 (19)	0.0041 (18)	0.0049 (17)
C8	0.0326 (18)	0.0298 (18)	0.0367 (19)	0.0173 (16)	0.0095 (15)	0.0084 (16)
C9	0.075 (3)	0.070 (3)	0.079 (3)	0.056 (3)	−0.023 (3)	−0.012 (3)
C10	0.048 (2)	0.037 (2)	0.069 (3)	0.0246 (19)	−0.011 (2)	0.003 (2)
C11	0.0298 (17)	0.0305 (18)	0.0291 (18)	0.0173 (15)	0.0013 (14)	0.0021 (14)
C12	0.0267 (17)	0.0367 (19)	0.037 (2)	0.0172 (16)	0.0074 (15)	0.0097 (16)
C13	0.043 (2)	0.054 (2)	0.035 (2)	0.0311 (19)	0.0023 (17)	0.0040 (17)
C14	0.048 (2)	0.065 (3)	0.053 (3)	0.033 (2)	0.015 (2)	0.029 (2)
C16	0.0323 (19)	0.037 (2)	0.042 (2)	0.0225 (17)	0.0021 (17)	−0.0013 (17)

Zn1—N5	1.914 (3)	N10—HW4	0.868 (18)
Zn1—N6	1.954 (3)	N11—C12	1.318 (4)
Zn1—N2i	2.011 (3)	N11—N12	1.395 (4)
Zn1—N1	2.012 (3)	N12—C11	1.309 (4)
Zn2—N16	1.926 (3)	N13—C12	1.344 (4)
Zn2—N15	1.962 (3)	N13—C11	1.359 (4)
Zn2—N7	1.990 (3)	N13—N14	1.410 (4)
Zn2—N11	2.000 (3)	N14—HW5	0.879 (18)
S1A—C5A	1.595 (10)	N14—HW6	0.871 (18)
C5A—N5	1.147 (10)	N16—C16	1.161 (4)
S1B—C5B	1.629 (12)	C1—C3	1.475 (5)
C5B—N5	1.173 (12)	C2—C4	1.474 (5)
S3A—C15A	1.600 (9)	C3—H3A	0.9700
C15A—N15	1.147 (8)	C3—H3B	0.9700
S3B—C15B	1.626 (13)	C3—H3C	0.9700
C15B—N15	1.158 (12)	C4—H4C	0.9700
S2—C6	1.624 (4)	C4—H4D	0.9700
S4—C16	1.615 (4)	C4—H4E	0.9700
N1—C2	1.310 (4)	C7—C9	1.485 (5)
N1—N2	1.395 (4)	C8—C10	1.485 (5)
N2—C1	1.315 (4)	C9—H9A	0.9700
N2—Zn1i	2.011 (3)	C9—H9B	0.9700
N3—C2	1.355 (4)	C9—H9C	0.9700
N3—C1	1.357 (4)	C10—H10C	0.9700
N3—N4	1.399 (4)	C10—H10D	0.9700
N4—HW1	0.889 (18)	C10—H10E	0.9700
N4—HW2	0.882 (18)	C11—C13	1.478 (5)
N6—C6	1.147 (5)	C12—C14	1.474 (5)
N7—C8	1.312 (4)	C13—H13A	0.9700
N7—N8	1.395 (4)	C13—H13B	0.9700
N8—C7	1.305 (4)	C13—H13C	0.9700
N9—C8	1.342 (4)	C14—H14C	0.9700
N9—C7	1.365 (5)	C14—H14D	0.9700
N9—N10	1.413 (4)	C14—H14E	0.9700
N10—HW3	0.853 (18)
N5—Zn1—N6	109.04 (14)	N2—C1—C3	127.0 (3)
N5—Zn1—N2i	115.00 (13)	N3—C1—C3	124.7 (3)
N6—Zn1—N2i	105.22 (12)	N1—C2—N3	108.2 (3)
N5—Zn1—N1	114.77 (12)	N1—C2—C4	127.1 (3)
N6—Zn1—N1	103.49 (12)	N3—C2—C4	124.7 (3)
N2i—Zn1—N1	108.28 (11)	C1—C3—H3A	109.5
N16—Zn2—N15	112.81 (14)	C1—C3—H3B	109.5
N16—Zn2—N7	112.84 (13)	H3A—C3—H3B	109.5
N15—Zn2—N7	106.15 (13)	C1—C3—H3C	109.5
N16—Zn2—N11	105.92 (12)	H3A—C3—H3C	109.5
N15—Zn2—N11	103.13 (12)	H3B—C3—H3C	109.5
N7—Zn2—N11	115.73 (11)	C2—C4—H4C	109.5
N5—C5A—S1A	177.3 (14)	C2—C4—H4D	109.5
N5—C5B—S1B	174.2 (18)	H4C—C4—H4D	109.5
N15—C15A—S3A	178.8 (7)	C2—C4—H4E	109.5
N15—C15B—S3B	174.4 (13)	H4C—C4—H4E	109.5
C2—N1—N2	108.0 (3)	H4D—C4—H4E	109.5
C2—N1—Zn1	127.6 (2)	N6—C6—S2	178.4 (4)
N2—N1—Zn1	122.2 (2)	N8—C7—N9	109.4 (3)
C1—N2—N1	107.5 (3)	N8—C7—C9	126.4 (4)
C1—N2—Zn1i	127.7 (2)	N9—C7—C9	124.2 (3)
N1—N2—Zn1i	122.1 (2)	N7—C8—N9	108.1 (3)
C2—N3—C1	108.1 (3)	N7—C8—C10	127.2 (3)
C2—N3—N4	129.1 (3)	N9—C8—C10	124.7 (3)
C1—N3—N4	122.8 (3)	C7—C9—H9A	109.5
N3—N4—HW1	108 (2)	C7—C9—H9B	109.5
N3—N4—HW2	109 (2)	H9A—C9—H9B	109.5
HW1—N4—HW2	103 (3)	C7—C9—H9C	109.5
C5A—N5—Zn1	164.9 (8)	H9A—C9—H9C	109.5
C5B—N5—Zn1	158.6 (10)	H9B—C9—H9C	109.5
C6—N6—Zn1	176.7 (3)	C8—C10—H10C	109.5
C8—N7—N8	108.9 (3)	C8—C10—H10D	109.5
C8—N7—Zn2	132.1 (2)	H10C—C10—H10D	109.5
N8—N7—Zn2	118.4 (2)	C8—C10—H10E	109.5
C7—N8—N7	106.2 (3)	H10C—C10—H10E	109.5
C8—N9—C7	107.5 (3)	H10D—C10—H10E	109.5
C8—N9—N10	123.4 (3)	N12—C11—N13	109.4 (3)
C7—N9—N10	128.7 (3)	N12—C11—C13	126.1 (3)
N9—N10—HW3	103 (3)	N13—C11—C13	124.5 (3)
N9—N10—HW4	108 (3)	N11—C12—N13	108.0 (3)
HW3—N10—HW4	114 (4)	N11—C12—C14	126.6 (3)
C12—N11—N12	108.5 (3)	N13—C12—C14	125.3 (3)
C12—N11—Zn2	128.6 (2)	C11—C13—H13A	109.5
N12—N11—Zn2	120.5 (2)	C11—C13—H13B	109.5
C11—N12—N11	106.4 (3)	H13A—C13—H13B	109.5
C12—N13—C11	107.6 (3)	C11—C13—H13C	109.5
C12—N13—N14	123.5 (3)	H13A—C13—H13C	109.5
C11—N13—N14	128.8 (3)	H13B—C13—H13C	109.5
N13—N14—HW5	105 (2)	C12—C14—H14C	109.5
N13—N14—HW6	106 (3)	C12—C14—H14D	109.5
HW5—N14—HW6	118 (4)	H14C—C14—H14D	109.5
C15A—N15—Zn2	163.6 (7)	C12—C14—H14E	109.5
C15B—N15—Zn2	148.3 (11)	H14C—C14—H14E	109.5
C16—N16—Zn2	167.0 (3)	H14D—C14—H14E	109.5
N2—C1—N3	108.2 (3)	N16—C16—S4	178.7 (3)
N5—Zn1—N1—C2	−39.3 (3)	N2—N1—C2—N3	1.0 (3)
N6—Zn1—N1—C2	79.4 (3)	Zn1—N1—C2—N3	−162.3 (2)
N2i—Zn1—N1—C2	−169.3 (3)	N2—N1—C2—C4	−178.2 (3)
N5—Zn1—N1—N2	159.6 (2)	Zn1—N1—C2—C4	18.5 (5)
N6—Zn1—N1—N2	−81.7 (2)	C1—N3—C2—N1	−0.8 (3)
N2i—Zn1—N1—N2	29.6 (3)	N4—N3—C2—N1	179.0 (3)
C2—N1—N2—C1	−0.8 (3)	C1—N3—C2—C4	178.5 (3)
Zn1—N1—N2—C1	163.5 (2)	N4—N3—C2—C4	−1.8 (5)
C2—N1—N2—Zn1i	162.0 (2)	N7—N8—C7—N9	−0.4 (4)
Zn1—N1—N2—Zn1i	−33.6 (3)	N7—N8—C7—C9	178.8 (4)
N16—Zn2—N7—C8	−66.9 (3)	C8—N9—C7—N8	0.8 (4)
N15—Zn2—N7—C8	169.0 (3)	N10—N9—C7—N8	173.8 (3)
N11—Zn2—N7—C8	55.3 (3)	C8—N9—C7—C9	−178.4 (4)
N16—Zn2—N7—N8	102.7 (2)	N10—N9—C7—C9	−5.4 (6)
N15—Zn2—N7—N8	−21.4 (3)	N8—N7—C8—N9	0.7 (4)
N11—Zn2—N7—N8	−135.1 (2)	Zn2—N7—C8—N9	171.0 (2)
C8—N7—N8—C7	−0.1 (4)	N8—N7—C8—C10	−178.8 (3)
Zn2—N7—N8—C7	−172.0 (2)	Zn2—N7—C8—C10	−8.4 (6)
N16—Zn2—N11—C12	−159.0 (3)	C7—N9—C8—N7	−0.9 (4)
N15—Zn2—N11—C12	−40.3 (3)	N10—N9—C8—N7	−174.3 (3)
N7—Zn2—N11—C12	75.2 (3)	C7—N9—C8—C10	178.5 (4)
N16—Zn2—N11—N12	1.3 (3)	N10—N9—C8—C10	5.1 (5)
N15—Zn2—N11—N12	120.0 (2)	N11—N12—C11—N13	0.5 (4)
N7—Zn2—N11—N12	−124.6 (2)	N11—N12—C11—C13	−178.4 (3)
C12—N11—N12—C11	−0.7 (4)	C12—N13—C11—N12	−0.2 (4)
Zn2—N11—N12—C11	−164.5 (2)	N14—N13—C11—N12	176.7 (3)
N15—Zn2—N16—C16	17.4 (14)	C12—N13—C11—C13	178.8 (3)
N7—Zn2—N16—C16	−102.9 (13)	N14—N13—C11—C13	−4.3 (5)
N11—Zn2—N16—C16	129.5 (13)	N12—N11—C12—N13	0.6 (4)
N1—N2—C1—N3	0.3 (3)	Zn2—N11—C12—N13	162.8 (2)
Zn1i—N2—C1—N3	−161.3 (2)	N12—N11—C12—C14	−179.4 (4)
N1—N2—C1—C3	179.9 (3)	Zn2—N11—C12—C14	−17.2 (5)
Zn1i—N2—C1—C3	18.3 (5)	C11—N13—C12—N11	−0.3 (4)
C2—N3—C1—N2	0.2 (4)	N14—N13—C12—N11	−177.4 (3)
N4—N3—C1—N2	−179.5 (3)	C11—N13—C12—C14	179.7 (4)
C2—N3—C1—C3	−179.3 (3)	N14—N13—C12—C14	2.6 (5)
N4—N3—C1—C3	0.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—HW1···S2ii	0.89 (2)	2.83 (3)	3.495 (3)	133 (3)
N4—HW2···N12	0.88 (2)	2.31 (2)	3.157 (4)	162 (3)
N10—HW3···N12iii	0.85 (2)	2.47 (2)	3.251 (4)	152 (3)
N10—HW4···S4iii	0.87 (2)	2.80 (2)	3.641 (4)	163 (3)
N14—HW5···N8iv	0.88 (2)	2.20 (2)	3.061 (4)	167 (3)
N14—HW6···S3Av	0.87 (2)	2.83 (3)	3.617 (9)	151 (3)
N14—HW6···S3Bv	0.87 (2)	2.83 (3)	3.542 (18)	140 (3)
C13—H13B···S3Av	0.97	2.82	3.458 (7)	124.

Table 1

Selected bond lengths (Å)

Zn1—N5	1.914 (3)
Zn1—N6	1.954 (3)
Zn1—N2i	2.011 (3)
Zn1—N1	2.012 (3)
Zn2—N16	1.926 (3)
Zn2—N15	1.962 (3)
Zn2—N7	1.990 (3)
Zn2—N11	2.000 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—HW1⋯S2ii	0.89 (2)	2.83 (3)	3.495 (3)	133 (3)
N4—HW2⋯N12	0.88 (2)	2.31 (2)	3.157 (4)	162 (3)
N10—HW3⋯N12iii	0.85 (2)	2.47 (2)	3.251 (4)	152 (3)
N10—HW4⋯S4iii	0.87 (2)	2.80 (2)	3.641 (4)	163 (3)
N14—HW5⋯N8iv	0.88 (2)	2.20 (2)	3.061 (4)	167 (3)
N14—HW6⋯S3Av	0.87 (2)	2.83 (3)	3.617 (9)	151 (3)
N14—HW6⋯S3Bv	0.87 (2)	2.83 (3)	3.542 (18)	140 (3)
C13—H13B⋯S3Av	0.97	2.82	3.458 (7)	124

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) .