Bis(N-isopropyl-N-methyl-dithio-carbamato-κS,S')(1,10-phenanthroline-κN,N')zinc.

The Zn(II) atom in the title compound, [Zn(C(5)H(10)NS(2))(2)(C(12)H(8)N(2))], exists in a distorted cis-octa-hedral N(2)S(4) donor set defined by two chelating dithio-carbamate anions as well as a 1,10-phenanthroline ligand. Each of the ligands coordinates in a symmetric mode. The crystal packing is stabilized by weak C-H⋯S, C-H⋯π(ZnS(2)C) and π-π [ring centroid distance between centrosymmetrically related pyridyl rings = 3.5955 (13) Å] inter-actions.

Related literature

For the use of the parent zinc compound and nitro­gen adducts as precursors for ZnS nanoparticles, see: Motevalli et al. (1996 ▶); Malik et al. (1997 ▶). For background to supra­molecular polymers of zinc-triad dithio­carbamates and related structures, see: Benson et al. (2007 ▶); Jamaluddin et al. (2011 ▶). For a description of C—H⋯π(MS2C) inter­actions, see: Tiekink & Zukerman-Schpector (2011 ▶).

Experimental

Crystal data

[Zn(C5H10NS2)2(C12H8N2)]

M = 542.09

Monoclinic,

a = 11.8015 (3) Å

b = 16.6316 (4) Å

c = 13.7505 (3) Å

β = 101.738 (2)°

V = 2642.48 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 150 K

0.25 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.777, T max = 0.860

33394 measured reflections

6001 independent reflections

4814 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.093

S = 1.04

6001 reflections

286 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012499/hb5835sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012499/hb5835Isup2.hkl

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

[Zn(C5H10NS2)2(C12H8N2)]	F(000) = 1128
Mr = 542.09	Dx = 1.363 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11977 reflections
a = 11.8015 (3) Å	θ = 2–29°
b = 16.6316 (4) Å	µ = 1.26 mm−1
c = 13.7505 (3) Å	T = 150 K
β = 101.738 (2)°	Prism, pale-yellow
V = 2642.48 (11) Å3	0.25 × 0.20 × 0.12 mm
Z = 4

Oxford Diffraction Xcaliber Eos Gemini diffractometer	6001 independent reflections
Radiation source: fine-focus sealed tube	4814 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 16.1952 pixels mm-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
Tmin = 0.777, Tmax = 0.860	l = −17→17
33394 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0376P)2 + 1.5727P] where P = (Fo2 + 2Fc2)/3
6001 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.66 e Å−3
6 restraints	Δρmin = −0.50 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Zn	0.74542 (2)	0.617296 (16)	0.733396 (19)	0.02087 (9)
S1	0.88167 (5)	0.51904 (4)	0.82966 (4)	0.02410 (14)
S2	0.94125 (6)	0.63431 (4)	0.68609 (4)	0.02614 (15)
S3	0.74451 (5)	0.71890 (4)	0.86753 (4)	0.02513 (15)
S4	0.57158 (5)	0.59097 (4)	0.80817 (4)	0.02474 (14)
N1	1.08885 (19)	0.52534 (15)	0.78012 (17)	0.0349 (5)
N2	0.55956 (18)	0.70121 (13)	0.94727 (15)	0.0289 (5)
N3	0.68974 (16)	0.53855 (11)	0.60453 (13)	0.0188 (4)
N4	0.65988 (16)	0.69879 (11)	0.61528 (14)	0.0206 (4)
C1	0.9824 (2)	0.55502 (15)	0.76623 (17)	0.0239 (5)
C2	1.1701 (3)	0.5547 (2)	0.7204 (3)	0.0553 (9)
H2A	1.1340	0.5512	0.6497	0.083*
H2B	1.2404	0.5218	0.7338	0.083*
H2C	1.1901	0.6108	0.7377	0.083*
C3	1.1290 (3)	0.45930 (18)	0.8512 (2)	0.0450 (8)
H3	1.0679	0.4513	0.8911	0.054*
C4	1.1391 (4)	0.3815 (2)	0.7977 (4)	0.0847 (14)
H4A	1.0650	0.3692	0.7534	0.127*
H4B	1.1594	0.3380	0.8463	0.127*
H4C	1.1995	0.3865	0.7586	0.127*
C5	1.2390 (3)	0.4817 (2)	0.9235 (3)	0.0609 (10)
H5A	1.3038	0.4822	0.8888	0.091*
H5B	1.2543	0.4422	0.9774	0.091*
H5C	1.2302	0.5351	0.9510	0.091*
C6	0.6178 (2)	0.67345 (14)	0.88098 (16)	0.0214 (5)
C7	0.5997 (3)	0.77392 (18)	1.0047 (2)	0.0433 (7)
H7A	0.6762	0.7640	1.0463	0.065*
H7B	0.5450	0.7878	1.0470	0.065*
H7C	0.6046	0.8185	0.9591	0.065*
C8	0.4491 (2)	0.66584 (18)	0.9609 (2)	0.0331 (6)
H8	0.4375	0.6144	0.9225	0.040*
C9	0.3502 (3)	0.7211 (2)	0.9181 (3)	0.0684 (11)
H9A	0.3586	0.7718	0.9551	0.103*
H9B	0.2768	0.6956	0.9234	0.103*
H9C	0.3507	0.7317	0.8481	0.103*
C10	0.4521 (3)	0.6458 (2)	1.0693 (2)	0.0504 (8)
H10A	0.5227	0.6155	1.0964	0.076*
H10B	0.3843	0.6133	1.0743	0.076*
H10C	0.4513	0.6957	1.1071	0.076*
C11	0.7038 (2)	0.45954 (14)	0.60029 (17)	0.0229 (5)
H11	0.7385	0.4319	0.6593	0.027*
C12	0.6698 (2)	0.41511 (14)	0.51280 (17)	0.0231 (5)
H12	0.6806	0.3585	0.5130	0.028*
C13	0.6210 (2)	0.45394 (14)	0.42725 (17)	0.0216 (5)
H13	0.5981	0.4246	0.3672	0.026*
C14	0.60452 (19)	0.53794 (14)	0.42823 (16)	0.0196 (5)
C15	0.64063 (18)	0.57743 (13)	0.51983 (16)	0.0168 (4)
C16	0.62276 (19)	0.66277 (13)	0.52604 (16)	0.0176 (5)
C17	0.56638 (19)	0.70521 (14)	0.44123 (16)	0.0200 (5)
C18	0.5324 (2)	0.66342 (15)	0.34901 (17)	0.0254 (5)
H18	0.4959	0.6921	0.2914	0.031*
C19	0.5516 (2)	0.58322 (15)	0.34272 (16)	0.0245 (5)
H19	0.5295	0.5568	0.2805	0.029*
C20	0.5474 (2)	0.78788 (14)	0.45176 (18)	0.0243 (5)
H20	0.5083	0.8185	0.3968	0.029*
C21	0.5854 (2)	0.82358 (15)	0.54158 (19)	0.0270 (5)
H21	0.5734	0.8795	0.5497	0.032*
C22	0.6422 (2)	0.77763 (14)	0.62167 (18)	0.0258 (5)
H22	0.6694	0.8036	0.6835	0.031*

	U11	U22	U33	U12	U13	U23
Zn	0.02263 (16)	0.02294 (16)	0.01688 (14)	0.00262 (11)	0.00360 (10)	−0.00228 (11)
S1	0.0225 (3)	0.0270 (3)	0.0237 (3)	0.0021 (2)	0.0069 (2)	0.0075 (2)
S2	0.0278 (3)	0.0285 (3)	0.0229 (3)	−0.0016 (3)	0.0070 (2)	0.0066 (3)
S3	0.0233 (3)	0.0283 (3)	0.0248 (3)	−0.0056 (2)	0.0073 (2)	−0.0095 (3)
S4	0.0247 (3)	0.0272 (3)	0.0226 (3)	−0.0051 (2)	0.0054 (2)	−0.0087 (2)
N1	0.0247 (12)	0.0447 (14)	0.0387 (12)	0.0059 (10)	0.0144 (10)	0.0145 (11)
N2	0.0262 (12)	0.0332 (12)	0.0304 (11)	−0.0037 (9)	0.0131 (9)	−0.0135 (10)
N3	0.0195 (10)	0.0179 (10)	0.0192 (9)	0.0016 (8)	0.0045 (7)	−0.0008 (8)
N4	0.0206 (10)	0.0198 (10)	0.0213 (9)	0.0018 (8)	0.0039 (8)	−0.0047 (8)
C1	0.0251 (13)	0.0258 (13)	0.0217 (11)	−0.0010 (10)	0.0071 (9)	−0.0021 (10)
C2	0.0346 (18)	0.078 (3)	0.061 (2)	0.0119 (16)	0.0263 (15)	0.0265 (19)
C3	0.0325 (16)	0.0416 (18)	0.065 (2)	0.0149 (13)	0.0184 (14)	0.0241 (16)
C4	0.080 (3)	0.049 (2)	0.119 (4)	0.018 (2)	0.007 (3)	0.003 (2)
C5	0.041 (2)	0.078 (3)	0.061 (2)	0.0160 (18)	0.0045 (16)	0.027 (2)
C6	0.0208 (12)	0.0241 (13)	0.0191 (11)	−0.0006 (9)	0.0034 (9)	−0.0035 (9)
C7	0.0447 (11)	0.0438 (11)	0.0440 (10)	−0.0024 (8)	0.0150 (8)	−0.0098 (8)
C8	0.0276 (15)	0.0411 (16)	0.0346 (14)	−0.0039 (12)	0.0155 (11)	−0.0053 (12)
C9	0.036 (2)	0.089 (3)	0.084 (3)	0.0108 (19)	0.0224 (18)	0.031 (2)
C10	0.061 (2)	0.056 (2)	0.0398 (17)	−0.0082 (17)	0.0231 (15)	−0.0037 (15)
C11	0.0230 (13)	0.0221 (12)	0.0233 (11)	0.0035 (10)	0.0042 (9)	0.0040 (10)
C12	0.0241 (13)	0.0176 (12)	0.0282 (12)	0.0024 (9)	0.0070 (10)	−0.0021 (10)
C13	0.0216 (12)	0.0206 (12)	0.0236 (11)	−0.0012 (9)	0.0071 (9)	−0.0044 (10)
C14	0.0176 (12)	0.0210 (12)	0.0209 (11)	−0.0019 (9)	0.0053 (9)	−0.0024 (9)
C15	0.0141 (11)	0.0177 (11)	0.0191 (10)	0.0002 (9)	0.0048 (8)	0.0000 (9)
C16	0.0161 (11)	0.0167 (11)	0.0205 (11)	−0.0011 (9)	0.0049 (8)	−0.0014 (9)
C17	0.0170 (12)	0.0200 (12)	0.0222 (11)	0.0004 (9)	0.0022 (9)	0.0007 (9)
C18	0.0283 (14)	0.0245 (13)	0.0207 (11)	−0.0016 (10)	−0.0019 (10)	0.0023 (10)
C19	0.0281 (14)	0.0278 (14)	0.0164 (11)	−0.0034 (10)	0.0013 (9)	−0.0021 (10)
C20	0.0224 (13)	0.0212 (13)	0.0285 (12)	0.0014 (10)	0.0029 (10)	0.0043 (10)
C21	0.0286 (14)	0.0175 (12)	0.0364 (14)	0.0033 (10)	0.0104 (11)	−0.0019 (10)
C22	0.0296 (14)	0.0216 (13)	0.0262 (12)	0.0021 (10)	0.0058 (10)	−0.0060 (10)

Zn—S1	2.4782 (6)	C7—H7A	0.9800
Zn—S2	2.5408 (7)	C7—H7B	0.9800
Zn—S3	2.5031 (6)	C7—H7C	0.9800
Zn—S4	2.5132 (7)	C8—C9	1.508 (4)
Zn—N3	2.1939 (18)	C8—C10	1.521 (4)
Zn—N4	2.1970 (19)	C8—H8	1.0000
S1—C1	1.719 (2)	C9—H9A	0.9800
S2—C1	1.724 (2)	C9—H9B	0.9800
S3—C6	1.718 (2)	C9—H9C	0.9800
S4—C6	1.720 (2)	C10—H10A	0.9800
N1—C1	1.326 (3)	C10—H10B	0.9800
N1—C2	1.467 (3)	C10—H10C	0.9800
N1—C3	1.483 (3)	C11—C12	1.399 (3)
N2—C6	1.331 (3)	C11—H11	0.9500
N2—C7	1.469 (3)	C12—C13	1.363 (3)
N2—C8	1.476 (3)	C12—H12	0.9500
N3—C11	1.327 (3)	C13—C14	1.411 (3)
N3—C15	1.355 (3)	C13—H13	0.9500
N4—C22	1.334 (3)	C14—C15	1.407 (3)
N4—C16	1.356 (3)	C14—C19	1.429 (3)
C2—H2A	0.9800	C15—C16	1.440 (3)
C2—H2B	0.9800	C16—C17	1.409 (3)
C2—H2C	0.9800	C17—C20	1.405 (3)
C3—C4	1.506 (5)	C17—C18	1.430 (3)
C3—C5	1.512 (5)	C18—C19	1.359 (4)
C3—H3	1.0000	C18—H18	0.9500
C4—H4A	0.9800	C19—H19	0.9500
C4—H4B	0.9800	C20—C21	1.362 (3)
C4—H4C	0.9800	C20—H20	0.9500
C5—H5A	0.9800	C21—C22	1.395 (3)
C5—H5B	0.9800	C21—H21	0.9500
C5—H5C	0.9800	C22—H22	0.9500
N3—Zn—N4	75.76 (7)	N2—C7—H7A	109.5
N3—Zn—S1	95.33 (5)	N2—C7—H7B	109.5
N4—Zn—S1	162.22 (5)	H7A—C7—H7B	109.5
N3—Zn—S3	162.30 (5)	N2—C7—H7C	109.5
N4—Zn—S3	93.33 (5)	H7A—C7—H7C	109.5
S1—Zn—S3	98.69 (2)	H7B—C7—H7C	109.5
N3—Zn—S4	95.23 (5)	N2—C8—C9	110.0 (2)
N4—Zn—S4	96.85 (5)	N2—C8—C10	111.5 (2)
S1—Zn—S4	99.30 (2)	C9—C8—C10	112.2 (3)
S3—Zn—S4	71.94 (2)	N2—C8—H8	107.7
N3—Zn—S2	89.90 (5)	C9—C8—H8	107.7
N4—Zn—S2	92.70 (5)	C10—C8—H8	107.7
S1—Zn—S2	71.65 (2)	C8—C9—H9A	109.5
S3—Zn—S2	104.71 (2)	C8—C9—H9B	109.5
S4—Zn—S2	170.02 (2)	H9A—C9—H9B	109.5
C1—S1—Zn	86.57 (8)	C8—C9—H9C	109.5
C1—S2—Zn	84.50 (8)	H9A—C9—H9C	109.5
C6—S3—Zn	85.22 (8)	H9B—C9—H9C	109.5
C6—S4—Zn	84.85 (8)	C8—C10—H10A	109.5
C1—N1—C2	120.2 (2)	C8—C10—H10B	109.5
C1—N1—C3	122.5 (2)	H10A—C10—H10B	109.5
C2—N1—C3	117.3 (2)	C8—C10—H10C	109.5
C6—N2—C7	119.9 (2)	H10A—C10—H10C	109.5
C6—N2—C8	122.8 (2)	H10B—C10—H10C	109.5
C7—N2—C8	117.2 (2)	N3—C11—C12	123.0 (2)
C11—N3—C15	118.04 (19)	N3—C11—H11	118.5
C11—N3—Zn	127.37 (15)	C12—C11—H11	118.5
C15—N3—Zn	114.51 (14)	C13—C12—C11	119.3 (2)
C22—N4—C16	117.9 (2)	C13—C12—H12	120.4
C22—N4—Zn	127.77 (15)	C11—C12—H12	120.4
C16—N4—Zn	114.32 (15)	C12—C13—C14	119.7 (2)
N1—C1—S1	121.99 (19)	C12—C13—H13	120.1
N1—C1—S2	120.82 (19)	C14—C13—H13	120.1
S1—C1—S2	117.15 (14)	C15—C14—C13	117.0 (2)
N1—C2—H2A	109.5	C15—C14—C19	119.5 (2)
N1—C2—H2B	109.5	C13—C14—C19	123.5 (2)
H2A—C2—H2B	109.5	N3—C15—C14	123.0 (2)
N1—C2—H2C	109.5	N3—C15—C16	117.49 (19)
H2A—C2—H2C	109.5	C14—C15—C16	119.45 (19)
H2B—C2—H2C	109.5	N4—C16—C17	122.6 (2)
N1—C3—C4	111.2 (3)	N4—C16—C15	117.71 (19)
N1—C3—C5	111.6 (3)	C17—C16—C15	119.66 (19)
C4—C3—C5	112.9 (3)	C20—C17—C16	117.6 (2)
N1—C3—H3	106.9	C20—C17—C18	123.0 (2)
C4—C3—H3	106.9	C16—C17—C18	119.4 (2)
C5—C3—H3	106.9	C19—C18—C17	120.9 (2)
C3—C4—H4A	109.5	C19—C18—H18	119.6
C3—C4—H4B	109.5	C17—C18—H18	119.6
H4A—C4—H4B	109.5	C18—C19—C14	121.0 (2)
C3—C4—H4C	109.5	C18—C19—H19	119.5
H4A—C4—H4C	109.5	C14—C19—H19	119.5
H4B—C4—H4C	109.5	C21—C20—C17	119.3 (2)
C3—C5—H5A	109.5	C21—C20—H20	120.3
C3—C5—H5B	109.5	C17—C20—H20	120.3
H5A—C5—H5B	109.5	C20—C21—C22	119.6 (2)
C3—C5—H5C	109.5	C20—C21—H21	120.2
H5A—C5—H5C	109.5	C22—C21—H21	120.2
H5B—C5—H5C	109.5	N4—C22—C21	122.9 (2)
N2—C6—S4	121.87 (19)	N4—C22—H22	118.5
N2—C6—S3	120.21 (18)	C21—C22—H22	118.5
S4—C6—S3	117.92 (14)
N3—Zn—S1—C1	85.85 (10)	C2—N1—C3—C5	56.7 (4)
N4—Zn—S1—C1	27.03 (19)	C7—N2—C6—S4	−177.3 (2)
S3—Zn—S1—C1	−104.98 (8)	C8—N2—C6—S4	−2.4 (3)
S4—Zn—S1—C1	−177.95 (8)	C7—N2—C6—S3	3.8 (3)
S2—Zn—S1—C1	−2.27 (8)	C8—N2—C6—S3	178.72 (19)
N3—Zn—S2—C1	−93.38 (9)	Zn—S4—C6—N2	178.5 (2)
N4—Zn—S2—C1	−169.12 (9)	Zn—S4—C6—S3	−2.66 (13)
S1—Zn—S2—C1	2.27 (8)	Zn—S3—C6—N2	−178.4 (2)
S3—Zn—S2—C1	96.72 (8)	Zn—S3—C6—S4	2.67 (13)
S4—Zn—S2—C1	27.68 (16)	C6—N2—C8—C9	−106.7 (3)
N3—Zn—S3—C6	43.33 (19)	C7—N2—C8—C9	68.4 (3)
N4—Zn—S3—C6	94.43 (9)	C6—N2—C8—C10	128.3 (3)
S1—Zn—S3—C6	−98.71 (8)	C7—N2—C8—C10	−56.7 (3)
S4—Zn—S3—C6	−1.70 (8)	C15—N3—C11—C12	−0.3 (3)
S2—Zn—S3—C6	−171.90 (8)	Zn—N3—C11—C12	−176.88 (17)
N3—Zn—S4—C6	−165.83 (9)	N3—C11—C12—C13	0.7 (4)
N4—Zn—S4—C6	−89.58 (9)	C11—C12—C13—C14	−0.6 (3)
S1—Zn—S4—C6	97.88 (8)	C12—C13—C14—C15	0.1 (3)
S3—Zn—S4—C6	1.70 (8)	C12—C13—C14—C19	−178.4 (2)
S2—Zn—S4—C6	73.51 (16)	C11—N3—C15—C14	−0.2 (3)
N4—Zn—N3—C11	−179.2 (2)	Zn—N3—C15—C14	176.82 (17)
S1—Zn—N3—C11	16.4 (2)	C11—N3—C15—C16	178.2 (2)
S3—Zn—N3—C11	−125.9 (2)	Zn—N3—C15—C16	−4.8 (2)
S4—Zn—N3—C11	−83.45 (19)	C13—C14—C15—N3	0.3 (3)
S2—Zn—N3—C11	87.97 (19)	C19—C14—C15—N3	178.9 (2)
N4—Zn—N3—C15	4.09 (15)	C13—C14—C15—C16	−178.1 (2)
S1—Zn—N3—C15	−160.28 (15)	C19—C14—C15—C16	0.5 (3)
S3—Zn—N3—C15	57.4 (3)	C22—N4—C16—C17	−0.3 (3)
S4—Zn—N3—C15	99.85 (15)	Zn—N4—C16—C17	−179.72 (17)
S2—Zn—N3—C15	−88.72 (15)	C22—N4—C16—C15	−179.2 (2)
N3—Zn—N4—C22	177.8 (2)	Zn—N4—C16—C15	1.5 (3)
S1—Zn—N4—C22	−120.7 (2)	N3—C15—C16—N4	2.2 (3)
S3—Zn—N4—C22	11.9 (2)	C14—C15—C16—N4	−179.3 (2)
S4—Zn—N4—C22	84.1 (2)	N3—C15—C16—C17	−176.6 (2)
S2—Zn—N4—C22	−93.0 (2)	C14—C15—C16—C17	1.9 (3)
N3—Zn—N4—C16	−2.91 (15)	N4—C16—C17—C20	−0.9 (3)
S1—Zn—N4—C16	58.6 (3)	C15—C16—C17—C20	177.9 (2)
S3—Zn—N4—C16	−168.78 (15)	N4—C16—C17—C18	178.4 (2)
S4—Zn—N4—C16	−96.59 (15)	C15—C16—C17—C18	−2.8 (3)
S2—Zn—N4—C16	86.31 (15)	C20—C17—C18—C19	−179.3 (2)
C2—N1—C1—S1	176.6 (2)	C16—C17—C18—C19	1.4 (4)
C3—N1—C1—S1	−0.1 (4)	C17—C18—C19—C14	1.0 (4)
C2—N1—C1—S2	−5.7 (4)	C15—C14—C19—C18	−2.0 (4)
C3—N1—C1—S2	177.6 (2)	C13—C14—C19—C18	176.5 (2)
Zn—S1—C1—N1	−178.6 (2)	C16—C17—C20—C21	1.2 (3)
Zn—S1—C1—S2	3.58 (13)	C18—C17—C20—C21	−178.1 (2)
Zn—S2—C1—N1	178.6 (2)	C17—C20—C21—C22	−0.2 (4)
Zn—S2—C1—S1	−3.50 (12)	C16—N4—C22—C21	1.4 (4)
C1—N1—C3—C4	106.4 (3)	Zn—N4—C22—C21	−179.31 (18)
C2—N1—C3—C4	−70.4 (4)	C20—C21—C22—N4	−1.1 (4)
C1—N1—C3—C5	−126.5 (3)

Cg1 is the centroid of the Zn,S1,S2,C1 chelate ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7b···S2i	0.98	2.79	3.734 (3)	162
C13—H13···S4ii	0.95	2.82	3.634 (2)	145
C21—H21···S1iii	0.95	2.84	3.684 (3)	149
C20—H20···Cg1iv	0.95	2.74	3.687 (2)	173

Table 1

Selected bond lengths (Å)

Zn—S1	2.4782 (6)
Zn—S2	2.5408 (7)
Zn—S3	2.5031 (6)
Zn—S4	2.5132 (7)
Zn—N3	2.1939 (18)
Zn—N4	2.1970 (19)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the Zn,S1,S2,C1 chelate ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7b⋯S2i	0.98	2.79	3.734 (3)	162
C13—H13⋯S4ii	0.95	2.82	3.634 (2)	145
C21—H21⋯S1iii	0.95	2.84	3.684 (3)	149
C20—H20⋯Cg1iv	0.95	2.74	3.687 (2)	173

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