{2-Morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}bis-(thio-cyanato-κN)zinc(II).

The asymmetric unit of the title compound, [Zn(NCS)(2)(C(13)H(19)N(3)O)], contains two crystallographically independent mol-ecules. In each mol-ecule, the Zn(II) ion is five-coordinated by the N,N',N"-tridentate Schiff base and the N atoms of two thio-cyanate ligands in a distorted square-pyramidal geometry. The two mol-ecules differ mainly in the deviations from the ideal geometry, with τ values of 0.14 and 0.33. In the crystal, inter-molecular C-H⋯S hydrogen bonds are observed. An intra-molecular C-H⋯N hydrogen bond occurs in one of the independent mol-ecules.

Related literature

For the crystal structures of similar zinc complexes, see: Cai (2009 ▶); Chen et al. (2005 ▶). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Zn(NCS)2(C13H19N3O)]

M = 414.84

Triclinic,

a = 9.9203 (2) Å

b = 13.5659 (2) Å

c = 14.6957 (2) Å

α = 112.702 (1)°

β = 91.471 (1)°

γ = 94.356 (1)°

V = 1815.97 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.59 mm−1

T = 100 K

0.42 × 0.33 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.554, T max = 0.691

15347 measured reflections

7111 independent reflections

6171 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.02

7111 reflections

435 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053778/vm2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053778/vm2068Isup2.hkl

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

[Zn(NCS)2(C13H19N3O)]	Z = 4
Mr = 414.84	F(000) = 856
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9203 (2) Å	Cell parameters from 7261 reflections
b = 13.5659 (2) Å	θ = 2.5–30.5°
c = 14.6957 (2) Å	µ = 1.59 mm−1
α = 112.702 (1)°	T = 100 K
β = 91.471 (1)°	Block, yellow
γ = 94.356 (1)°	0.42 × 0.33 × 0.25 mm
V = 1815.97 (5) Å3

Bruker APEXII CCD diffractometer	7111 independent reflections
Radiation source: fine-focus sealed tube	6171 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.554, Tmax = 0.691	k = −16→16
15347 measured reflections	l = −17→18

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.8172P] where P = (Fo2 + 2Fc2)/3
7111 reflections	(Δ/σ)max = 0.001
435 parameters	Δρmax = 0.63 e Å−3
5 restraints	Δρmin = −0.27 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
Zn1	0.19481 (2)	0.410155 (19)	0.190924 (17)	0.01900 (7)
S1	0.18204 (6)	0.44706 (5)	0.52312 (4)	0.03297 (15)
S2	0.49821 (6)	0.67240 (5)	0.15470 (4)	0.02846 (13)
O1	0.49220 (16)	0.27533 (15)	0.32934 (13)	0.0348 (4)
N1	−0.00833 (17)	0.43646 (14)	0.15397 (12)	0.0199 (4)
N2	0.15687 (17)	0.30747 (14)	0.04303 (12)	0.0203 (4)
N3	0.37745 (17)	0.31359 (15)	0.16386 (13)	0.0220 (4)
N4	0.15900 (18)	0.42921 (16)	0.32803 (13)	0.0258 (4)
C1	−0.0848 (2)	0.50901 (18)	0.21249 (16)	0.0250 (5)
H1	−0.0550	0.5474	0.2799	0.030*
C2	−0.2065 (2)	0.53031 (19)	0.17825 (18)	0.0295 (5)
H2	−0.2585	0.5832	0.2213	0.035*
C3	−0.2508 (2)	0.47373 (19)	0.08096 (17)	0.0292 (5)
H3	−0.3335	0.4873	0.0559	0.035*
C4	−0.1727 (2)	0.39631 (19)	0.01981 (17)	0.0257 (5)
H4	−0.2022	0.3550	−0.0472	0.031*
C5	−0.0514 (2)	0.38077 (17)	0.05858 (15)	0.0203 (4)
C6	0.0427 (2)	0.30383 (17)	−0.00108 (15)	0.0207 (4)
C7	−0.0008 (2)	0.2307 (2)	−0.10502 (16)	0.0303 (5)
H7A	0.0643	0.1770	−0.1305	0.045*
H7B	−0.0046	0.2726	−0.1462	0.045*
H7C	−0.0906	0.1945	−0.1065	0.045*
C8	0.2657 (2)	0.24304 (18)	−0.00450 (16)	0.0251 (5)
H8A	0.2741	0.2412	−0.0721	0.030*
H8B	0.2468	0.1685	−0.0090	0.030*
C9	0.3955 (2)	0.29495 (19)	0.05839 (16)	0.0260 (5)
H9A	0.4692	0.2479	0.0337	0.031*
H9B	0.4218	0.3642	0.0529	0.031*
C10	0.3596 (2)	0.20758 (18)	0.17256 (17)	0.0258 (5)
H10A	0.4307	0.1628	0.1369	0.031*
H10B	0.2706	0.1705	0.1409	0.031*
C11	0.3674 (2)	0.2191 (2)	0.27917 (17)	0.0292 (5)
H11A	0.2912	0.2582	0.3134	0.035*
H11B	0.3584	0.1469	0.2815	0.035*
C12	0.5035 (2)	0.3799 (2)	0.32699 (18)	0.0331 (6)
H12A	0.5884	0.4205	0.3637	0.040*
H12B	0.4266	0.4192	0.3599	0.040*
C13	0.5035 (2)	0.3728 (2)	0.22158 (18)	0.0290 (5)
H13A	0.5125	0.4461	0.2219	0.035*
H13B	0.5823	0.3359	0.1896	0.035*
C14	0.1676 (2)	0.43803 (17)	0.41001 (16)	0.0214 (4)
C15	0.3793 (2)	0.59693 (16)	0.17611 (15)	0.0194 (4)
Zn2	0.30417 (2)	0.953591 (19)	0.691039 (17)	0.01820 (7)
S3	0.65029 (6)	1.07952 (5)	0.92910 (4)	0.03050 (14)
S4	0.05616 (6)	1.21315 (5)	0.63775 (4)	0.02613 (13)
O2	0.06613 (17)	0.85681 (14)	0.89498 (12)	0.0358 (4)
N5	0.29418 (19)	0.54316 (15)	0.19158 (14)	0.0279 (4)
N6	0.49783 (18)	0.98236 (14)	0.63008 (13)	0.0220 (4)
N7	0.31286 (18)	0.82075 (14)	0.56062 (12)	0.0213 (4)
N8	0.12340 (17)	0.84559 (14)	0.69974 (13)	0.0222 (4)
N9	0.40186 (18)	1.00133 (15)	0.82261 (13)	0.0241 (4)
N10	0.19805 (19)	1.06809 (15)	0.68484 (14)	0.0261 (4)
C16	0.5889 (2)	1.06648 (18)	0.67001 (16)	0.0268 (5)
H16	0.5638	1.1284	0.7224	0.032*
C17	0.7190 (2)	1.0676 (2)	0.63832 (17)	0.0301 (5)
H17	0.7814	1.1295	0.6675	0.036*
C18	0.7562 (2)	0.9774 (2)	0.56381 (17)	0.0333 (6)
H18	0.8453	0.9755	0.5415	0.040*
C19	0.6615 (2)	0.8887 (2)	0.52143 (17)	0.0304 (5)
H19	0.6847	0.8256	0.4695	0.036*
C20	0.5332 (2)	0.89417 (17)	0.55625 (15)	0.0215 (4)
C21	0.4233 (2)	0.80383 (18)	0.51743 (15)	0.0232 (5)
C22	0.4504 (3)	0.7028 (2)	0.43377 (17)	0.0346 (6)
H22A	0.3674	0.6537	0.4134	0.052*
H22B	0.5214	0.6686	0.4551	0.052*
H22C	0.4801	0.7197	0.3780	0.052*
C23	0.1933 (2)	0.74271 (18)	0.53134 (16)	0.0274 (5)
H23A	0.2126	0.6777	0.5428	0.033*
H23B	0.1678	0.7213	0.4603	0.033*
C24	0.0797 (2)	0.79550 (19)	0.59319 (16)	0.0279 (5)
H24A	0.0490	0.8511	0.5714	0.033*
H24B	0.0022	0.7411	0.5831	0.033*
C25	0.0097 (2)	0.9010 (2)	0.75502 (17)	0.0299 (5)
H25A	−0.0732	0.8505	0.7369	0.036*
H25B	−0.0076	0.9618	0.7362	0.036*
C26	0.0408 (3)	0.9423 (2)	0.86506 (18)	0.0344 (6)
H26A	0.1213	0.9954	0.8837	0.041*
H26B	−0.0366	0.9789	0.8999	0.041*
C27	0.1808 (2)	0.8079 (2)	0.84673 (17)	0.0297 (5)
H27A	0.2018	0.7504	0.8690	0.036*
H27B	0.2601	0.8621	0.8656	0.036*
C28	0.1563 (2)	0.76110 (18)	0.73578 (16)	0.0257 (5)
H28A	0.2382	0.7286	0.7048	0.031*
H28B	0.0805	0.7038	0.7163	0.031*
C29	0.5052 (2)	1.03434 (17)	0.86717 (15)	0.0221 (4)
C30	0.1385 (2)	1.12873 (17)	0.66588 (15)	0.0195 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.01919 (13)	0.02094 (13)	0.01724 (13)	−0.00064 (10)	−0.00103 (9)	0.00842 (10)
S1	0.0416 (3)	0.0372 (3)	0.0187 (3)	−0.0095 (3)	−0.0067 (2)	0.0122 (2)
S2	0.0309 (3)	0.0258 (3)	0.0314 (3)	0.0019 (2)	0.0092 (2)	0.0139 (2)
O1	0.0272 (9)	0.0481 (11)	0.0368 (10)	0.0044 (8)	−0.0064 (7)	0.0254 (9)
N1	0.0206 (9)	0.0204 (9)	0.0189 (9)	−0.0010 (7)	−0.0006 (7)	0.0085 (7)
N2	0.0224 (9)	0.0217 (9)	0.0178 (9)	0.0009 (7)	0.0016 (7)	0.0090 (7)
N3	0.0185 (9)	0.0266 (10)	0.0238 (9)	0.0001 (7)	−0.0003 (7)	0.0135 (8)
N4	0.0226 (9)	0.0338 (11)	0.0218 (10)	0.0031 (8)	0.0016 (8)	0.0115 (8)
C1	0.0268 (11)	0.0226 (11)	0.0227 (11)	0.0014 (9)	0.0001 (9)	0.0060 (9)
C2	0.0265 (12)	0.0270 (12)	0.0325 (13)	0.0050 (10)	0.0035 (10)	0.0085 (10)
C3	0.0220 (11)	0.0356 (13)	0.0326 (13)	0.0024 (10)	−0.0024 (10)	0.0166 (11)
C4	0.0235 (11)	0.0305 (12)	0.0233 (11)	−0.0014 (9)	−0.0034 (9)	0.0116 (10)
C5	0.0202 (10)	0.0220 (11)	0.0201 (11)	−0.0032 (8)	−0.0008 (8)	0.0107 (9)
C6	0.0233 (11)	0.0231 (11)	0.0176 (10)	−0.0007 (9)	0.0018 (8)	0.0104 (9)
C7	0.0302 (12)	0.0398 (14)	0.0171 (11)	0.0030 (11)	−0.0005 (9)	0.0070 (10)
C8	0.0259 (11)	0.0291 (12)	0.0205 (11)	0.0062 (9)	0.0045 (9)	0.0091 (9)
C9	0.0231 (11)	0.0328 (13)	0.0259 (12)	0.0058 (9)	0.0059 (9)	0.0146 (10)
C10	0.0236 (11)	0.0276 (12)	0.0301 (12)	0.0033 (9)	0.0014 (9)	0.0154 (10)
C11	0.0285 (12)	0.0334 (13)	0.0335 (13)	0.0038 (10)	0.0003 (10)	0.0216 (11)
C12	0.0208 (11)	0.0426 (15)	0.0356 (14)	−0.0012 (10)	−0.0070 (10)	0.0163 (12)
C13	0.0187 (11)	0.0347 (13)	0.0354 (13)	0.0004 (10)	−0.0016 (9)	0.0162 (11)
C14	0.0202 (10)	0.0221 (11)	0.0208 (9)	−0.0014 (8)	−0.0018 (8)	0.0080 (9)
C15	0.0252 (10)	0.0166 (10)	0.0155 (10)	0.0041 (8)	−0.0013 (8)	0.0050 (8)
Zn2	0.01948 (13)	0.01887 (13)	0.01650 (12)	0.00159 (9)	−0.00018 (9)	0.00725 (10)
S3	0.0260 (3)	0.0318 (3)	0.0302 (3)	−0.0036 (2)	−0.0090 (2)	0.0100 (3)
S4	0.0305 (3)	0.0271 (3)	0.0246 (3)	0.0090 (2)	0.0018 (2)	0.0131 (2)
O2	0.0370 (9)	0.0446 (11)	0.0289 (9)	−0.0068 (8)	0.0065 (7)	0.0194 (8)
N5	0.0326 (11)	0.0255 (10)	0.0265 (10)	−0.0047 (8)	−0.0059 (8)	0.0130 (8)
N6	0.0259 (9)	0.0223 (9)	0.0187 (9)	0.0026 (8)	0.0026 (7)	0.0089 (8)
N7	0.0276 (10)	0.0198 (9)	0.0170 (9)	0.0005 (7)	−0.0033 (7)	0.0086 (7)
N8	0.0202 (9)	0.0255 (10)	0.0210 (9)	−0.0024 (7)	−0.0029 (7)	0.0102 (8)
N9	0.0250 (10)	0.0276 (10)	0.0198 (9)	−0.0015 (8)	−0.0007 (8)	0.0101 (8)
N10	0.0296 (10)	0.0273 (10)	0.0250 (10)	0.0069 (8)	0.0042 (8)	0.0132 (8)
C16	0.0314 (12)	0.0253 (12)	0.0235 (11)	0.0001 (10)	0.0018 (9)	0.0098 (10)
C17	0.0308 (12)	0.0376 (14)	0.0230 (12)	−0.0053 (10)	0.0011 (10)	0.0146 (10)
C18	0.0272 (12)	0.0524 (16)	0.0244 (12)	0.0039 (11)	0.0069 (10)	0.0190 (12)
C19	0.0339 (13)	0.0380 (14)	0.0199 (11)	0.0090 (11)	0.0064 (10)	0.0106 (10)
C20	0.0279 (11)	0.0256 (11)	0.0136 (10)	0.0071 (9)	0.0021 (8)	0.0095 (9)
C21	0.0334 (12)	0.0245 (11)	0.0136 (10)	0.0073 (9)	−0.0017 (9)	0.0089 (9)
C22	0.0460 (15)	0.0313 (13)	0.0214 (12)	0.0067 (11)	0.0035 (11)	0.0040 (10)
C23	0.0358 (13)	0.0253 (12)	0.0185 (11)	−0.0049 (10)	−0.0071 (9)	0.0077 (9)
C24	0.0259 (11)	0.0317 (13)	0.0240 (12)	−0.0073 (10)	−0.0087 (9)	0.0112 (10)
C25	0.0222 (11)	0.0342 (13)	0.0351 (13)	−0.0021 (10)	0.0003 (10)	0.0166 (11)
C26	0.0303 (13)	0.0373 (14)	0.0337 (13)	−0.0030 (11)	0.0070 (10)	0.0123 (11)
C27	0.0306 (12)	0.0352 (13)	0.0261 (12)	−0.0081 (10)	−0.0031 (10)	0.0172 (10)
C28	0.0256 (11)	0.0265 (12)	0.0270 (12)	−0.0061 (9)	−0.0028 (9)	0.0144 (10)
C29	0.0244 (10)	0.0232 (11)	0.0186 (10)	0.0015 (8)	0.0009 (8)	0.0084 (9)
C30	0.0208 (10)	0.0203 (10)	0.0168 (10)	0.0005 (8)	0.0024 (8)	0.0067 (8)

Zn1—N4	1.9752 (18)	Zn2—N10	1.9702 (19)
Zn1—N5	1.9858 (19)	Zn2—N9	1.9847 (18)
Zn1—N2	2.0851 (17)	Zn2—N7	2.0724 (18)
Zn1—N1	2.1647 (17)	Zn2—N6	2.2113 (18)
Zn1—N3	2.2698 (18)	Zn2—N8	2.2662 (17)
S1—C14	1.621 (2)	S3—C29	1.626 (2)
S2—C15	1.620 (2)	S4—C30	1.625 (2)
O1—C11	1.426 (3)	O2—C27	1.424 (3)
O1—C12	1.428 (3)	O2—C26	1.426 (3)
N1—C1	1.333 (3)	N6—C16	1.328 (3)
N1—C5	1.349 (3)	N6—C20	1.346 (3)
N2—C6	1.278 (3)	N7—C21	1.272 (3)
N2—C8	1.459 (3)	N7—C23	1.464 (3)
N3—C13	1.481 (3)	N8—C25	1.484 (3)
N3—C9	1.489 (3)	N8—C24	1.483 (3)
N3—C10	1.490 (3)	N8—C28	1.489 (3)
N4—C14	1.164 (3)	N9—C29	1.162 (3)
C1—C2	1.389 (3)	N10—C30	1.160 (3)
C1—H1	0.9500	C16—C17	1.384 (3)
C2—C3	1.377 (3)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.374 (3)
C3—C4	1.393 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.392 (3)
C4—C5	1.383 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.380 (3)
C5—C6	1.488 (3)	C19—H19	0.9500
C6—C7	1.495 (3)	C20—C21	1.497 (3)
C7—H7A	0.9800	C21—C22	1.495 (3)
C7—H7B	0.9800	C22—H22A	0.9800
C7—H7C	0.9800	C22—H22B	0.9800
C8—C9	1.518 (3)	C22—H22C	0.9800
C8—H8A	0.9900	C23—C24	1.511 (3)
C8—H8B	0.9900	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	C24—H24A	0.9900
C10—C11	1.513 (3)	C24—H24B	0.9900
C10—H10A	0.9900	C25—C26	1.508 (3)
C10—H10B	0.9900	C25—H25A	0.9900
C11—H11A	0.9900	C25—H25B	0.9900
C11—H11B	0.9900	C26—H26A	0.9900
C12—C13	1.514 (3)	C26—H26B	0.9900
C12—H12A	0.9900	C27—C28	1.509 (3)
C12—H12B	0.9900	C27—H27A	0.9900
C13—H13A	0.9900	C27—H27B	0.9900
C13—H13B	0.9900	C28—H28A	0.9900
C15—N5	1.158 (3)	C28—H28B	0.9900
N4—Zn1—N5	109.20 (8)	N10—Zn2—N7	116.72 (7)
N4—Zn1—N2	144.10 (7)	N9—Zn2—N7	132.79 (7)
N5—Zn1—N2	106.50 (7)	N10—Zn2—N6	103.26 (7)
N4—Zn1—N1	94.84 (7)	N9—Zn2—N6	88.45 (7)
N5—Zn1—N1	99.47 (7)	N7—Zn2—N6	74.79 (7)
N2—Zn1—N1	75.52 (7)	N10—Zn2—N8	95.58 (7)
N4—Zn1—N3	101.50 (7)	N9—Zn2—N8	104.11 (7)
N5—Zn1—N3	95.61 (7)	N7—Zn2—N8	78.69 (7)
N2—Zn1—N3	78.47 (7)	N6—Zn2—N8	152.32 (7)
N1—Zn1—N3	152.73 (7)	C27—O2—C26	108.42 (17)
C11—O1—C12	108.95 (17)	C15—N5—Zn1	158.34 (19)
C1—N1—C5	118.96 (18)	C16—N6—C20	118.93 (19)
C1—N1—Zn1	126.23 (14)	C16—N6—Zn2	126.84 (15)
C5—N1—Zn1	114.37 (14)	C20—N6—Zn2	112.82 (14)
C6—N2—C8	123.61 (18)	C21—N7—C23	123.23 (19)
C6—N2—Zn1	119.77 (15)	C21—N7—Zn2	120.06 (15)
C8—N2—Zn1	116.62 (13)	C23—N7—Zn2	116.11 (14)
C13—N3—C9	107.76 (16)	C25—N8—C24	108.46 (17)
C13—N3—C10	108.19 (17)	C25—N8—C28	108.55 (17)
C9—N3—C10	108.54 (17)	C24—N8—C28	109.78 (17)
C13—N3—Zn1	114.89 (14)	C25—N8—Zn2	115.82 (13)
C9—N3—Zn1	99.80 (12)	C24—N8—Zn2	98.72 (13)
C10—N3—Zn1	116.86 (13)	C28—N8—Zn2	114.90 (13)
C14—N4—Zn1	165.19 (18)	C29—N9—Zn2	145.54 (17)
N1—C1—C2	122.2 (2)	C30—N10—Zn2	169.54 (18)
N1—C1—H1	118.9	N6—C16—C17	122.6 (2)
C2—C1—H1	118.9	N6—C16—H16	118.7
C3—C2—C1	119.0 (2)	C17—C16—H16	118.7
C3—C2—H2	120.5	C18—C17—C16	118.7 (2)
C1—C2—H2	120.5	C18—C17—H17	120.6
C2—C3—C4	119.1 (2)	C16—C17—H17	120.6
C2—C3—H3	120.5	C17—C18—C19	119.1 (2)
C4—C3—H3	120.5	C17—C18—H18	120.4
C5—C4—C3	118.7 (2)	C19—C18—H18	120.4
C5—C4—H4	120.7	C20—C19—C18	118.7 (2)
C3—C4—H4	120.7	C20—C19—H19	120.6
N1—C5—C4	122.0 (2)	C18—C19—H19	120.6
N1—C5—C6	114.78 (18)	N6—C20—C19	121.9 (2)
C4—C5—C6	123.18 (19)	N6—C20—C21	114.45 (18)
N2—C6—C5	115.26 (18)	C19—C20—C21	123.7 (2)
N2—C6—C7	125.6 (2)	N7—C21—C22	125.4 (2)
C5—C6—C7	119.15 (18)	N7—C21—C20	115.53 (19)
C6—C7—H7A	109.5	C22—C21—C20	119.0 (2)
C6—C7—H7B	109.5	C21—C22—H22A	109.5
H7A—C7—H7B	109.5	C21—C22—H22B	109.5
C6—C7—H7C	109.5	H22A—C22—H22B	109.5
H7A—C7—H7C	109.5	C21—C22—H22C	109.5
H7B—C7—H7C	109.5	H22A—C22—H22C	109.5
N2—C8—C9	107.21 (18)	H22B—C22—H22C	109.5
N2—C8—H8A	110.3	N7—C23—C24	107.55 (18)
C9—C8—H8A	110.3	N7—C23—H23A	110.2
N2—C8—H8B	110.3	C24—C23—H23A	110.2
C9—C8—H8B	110.3	N7—C23—H23B	110.2
H8A—C8—H8B	108.5	C24—C23—H23B	110.2
N3—C9—C8	110.92 (17)	H23A—C23—H23B	108.5
N3—C9—H9A	109.5	N8—C24—C23	111.46 (18)
C8—C9—H9A	109.5	N8—C24—H24A	109.3
N3—C9—H9B	109.5	C23—C24—H24A	109.3
C8—C9—H9B	109.5	N8—C24—H24B	109.3
H9A—C9—H9B	108.0	C23—C24—H24B	109.3
N3—C10—C11	111.94 (19)	H24A—C24—H24B	108.0
N3—C10—H10A	109.2	N8—C25—C26	111.31 (19)
C11—C10—H10A	109.2	N8—C25—H25A	109.4
N3—C10—H10B	109.2	C26—C25—H25A	109.4
C11—C10—H10B	109.2	N8—C25—H25B	109.4
H10A—C10—H10B	107.9	C26—C25—H25B	109.4
O1—C11—C10	111.59 (18)	H25A—C25—H25B	108.0
O1—C11—H11A	109.3	O2—C26—C25	111.0 (2)
C10—C11—H11A	109.3	O2—C26—H26A	109.4
O1—C11—H11B	109.3	C25—C26—H26A	109.4
C10—C11—H11B	109.3	O2—C26—H26B	109.4
H11A—C11—H11B	108.0	C25—C26—H26B	109.4
O1—C12—C13	110.8 (2)	H26A—C26—H26B	108.0
O1—C12—H12A	109.5	O2—C27—C28	111.75 (19)
C13—C12—H12A	109.5	O2—C27—H27A	109.3
O1—C12—H12B	109.5	C28—C27—H27A	109.3
C13—C12—H12B	109.5	O2—C27—H27B	109.3
H12A—C12—H12B	108.1	C28—C27—H27B	109.3
N3—C13—C12	111.49 (18)	H27A—C27—H27B	107.9
N3—C13—H13A	109.3	N8—C28—C27	110.69 (19)
C12—C13—H13A	109.3	N8—C28—H28A	109.5
N3—C13—H13B	109.3	C27—C28—H28A	109.5
C12—C13—H13B	109.3	N8—C28—H28B	109.5
H13A—C13—H13B	108.0	C27—C28—H28B	109.5
N4—C14—S1	178.3 (2)	H28A—C28—H28B	108.1
N5—C15—S2	179.9 (3)	N9—C29—S3	179.5 (2)
N10—Zn2—N9	109.96 (8)	N10—C30—S4	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···S1i	0.99	2.84	3.826 (2)	175
C16—H16···S2ii	0.95	2.74	3.670 (2)	168
C27—H27B···N9	0.99	2.55	3.421 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯S1i	0.99	2.84	3.826 (2)	175
C16—H16⋯S2ii	0.95	2.74	3.670 (2)	168
C27—H27B⋯N9	0.99	2.55	3.421 (3)	147

Symmetry codes: (i) ; (ii) .