Two isomorphous Zn^II/Co^II complexes with tri-tert-butoxy­silanethiol and histamine, and (4-hydroxy­methyl-1H-imidazole-κN)bis­(tri-tert-butoxy­silanethiol­ato-κ²O,S)zinc(II)

The complexes [2-(1H-imidazol-4-yl-κN³)ethyl­amine-κN]bis­(tri-tert-butoxy­silanethiol­ato-κS)cobalt(II), [Co(C₁₂H₂₇O₃SSi)₂(C₅H₉N₃)], and [2-(1H-imidazol-4-yl-κN³)ethyl­amine-κN]bis­(tri-tert-butoxy­silanethiol­ato-κS)zinc(II), [Zn(C₁₂H₂₇O₃SSi)₂(C₅H₉N₃)], are isomorphous. The central Zn^II/Co^II ions are surrounded by two S atoms from the tri-tert-butoxy­silanethiol­ate ligand and by two N atoms from the chelating histamine ligand in a distorted tetra­hedral geometry, with two intra­molecular N—H...O hydrogen-bonding inter­actions between the histamine NH₂ groups and tert-but­oxy O atoms. Mol­ecules of the complexes are joined into dimers via two inter­molecular bifurcated N—H...(S,O) hydrogen bonds. The Zn^II atom in [(1H-imidazol-4-yl-κN³)methanol]bis(tri-tert-butoxy­silanethiol­ato-κ²O,S)zinc(II), [Zn(C₁₂H₂₇O₃SSi)₂(C₄H₆N₂O)], is five-coordinated by two O and two S atoms from the O,S-chelating silanethiol­ate ligand and by one N atom from (1H-imidazol-4-yl)methanol; the hydr­oxy group forms an intra­molecular hydrogen bond with sulfur. Mol­ecules of this complex pack as zigzag chains linked by N—H...O hydrogen bonds. These structures provide reference details for cysteine- and histidine-ligated metal centers in proteins.

S1. Comment

Structural and spectroscopic studies on heteroleptic, transition metal tri-tert-butoxysilanethiolates have been undertaken to provide a source of reference data for cysteine-ligated metal centers in proteins (Becker, Zalewska et al., 2001; Becker et al., 2002; Dołęga et al., 2004, 2007, 2008; Kropidłowska et al., 2007). Unfortunately, ¹¹³Cd NMR and UV–vis solution studies revealed low stability of these complexes; in solution N-containing ligands are discarded and homoleptic metal thiolates restored (Becker, Zalewska et al., 2001; Dołęga et al., 2007; Dołęga & Walewski, 2007). We have not noticed any correlation between ligand–metal bond lengths in solids and the stability of the obtained complexes in solution. Even complexes with short metal–nitrogen bonds in the solid state, such as imidazole derivatives, tend to dissociate (Dołęga et al., 2007). Since our aim is to obtain solution UV–vis and NMR spectroscopic parameters correlated with well defined metal coordination, we decided to use N-containing ligands with additional chelating OH and NH₂ groups in order to stabilize the resulting species in solution (Barszcz, 2005). Histamine, (I), and 4(5)-hydroxymethylimidazole, (II), have been applied as potentially chelating ligands. The crystal structures of one Co^II and two Zn^II complexes have been determined.

The molecular structure of [2-(1H-imidazol-4-yl-κN³)ethylamine- κ²N]bis(tri-tert-butoxysilanethiolato-κS)cobalt(II), (III), is presented in Fig. 1. The zinc analogue, (IV), is isomorphic; geometrical parameters are compared in Table 4. As in some previously described complexes (eg. Wojtczak et al., 1990; Garnuszek et al., 2002), histamine acts as a bidentate ligand, forming a six-membered ring including the metal ion, the latter displaying a distorted tetrahedral geometry in (III0 and (IV). Complexation of the amine N atom with the metal ion is stabilized by hydrogen bonds with O atoms from the tri-tert-butoxysilanethiolate ligands. These additional intramolecular interactions influence the regularity of the crystal packing of molecular tri-tert-butoxysilanethiolates; bulky, alkoxy substituents of tri-tert-butoxysilanethiol often exhibit static disorder in crystals (Kloskowska et al., 2006). Sometimes it is not possible to find an appropriate model for the disordered groups – such results then remain unpublished. If intramolecular hydrogen bonds are formed between ligands and adjacent tert-butoxy groups, the possibility of rotation and disorder is significantly diminished (Becker, Dołęga et al., 2001, Dołęga et al., 2006, 2008). In (III) and (IV), the methyl groups at C21 exhibit disorder and so were refined over two positions. The refinement of (IV) was stable without additional constraints; in (III), atom pairs based on C23 and C24 were refined with isotropic displacement parameters.

Compounds (III) and (IV) are the first structurally characterized complexes of histamine with Zn^II and Co^II. The geometrical parameters of Zn^II-bonded histamine are comparable to those of other N¹,N³-chelating histidine ligands in complexes with zinc(II) (Harding & Cole, 1963; Dalosto et al., 2001). The bond lengths found in (III) are in the range typical for neutral, tetrahedral Co^II complexes with imidazole-based and tri-tert-butoxysilanethiolate ligands (Becker, Zalewska et al., 2001; Dołęga et al., 2008). The Co—N bond lengths in a known complex of Co^III with histamine are certainly shorter than those in (III), but the chelating angles are close to those in (III) (Wojtczak et al., 1990). Our results confirm the structural similarity of tetrahedral Zn^II and Co^II complexes with the same ligands (Horrocks et al., 1982; Dołęga et al., 2008).

Centrosymmetrically related molecules of (III) and (IV) form hydrogen-bonded dimers (Table 1), which are shown in Fig. 2. The planes of the imidazole rings are parallel, but there are no stacking interactions because of the inter-ring distance.

2-Hydroxymethylimidazole does not act as a bidentate chelating ligand in [2-(1H-imidazol-4-yl-κN³)methanol]bis(tri-tert-butoxysilanethiolato-κ²O,S)zinc(II), (V), but rather is bonded to zinc only via an N atom of the imidazole ring (Fig. 3). Ignoring the assymetric conformation of the imidazole ring, (V) would exhibit an approximate twofold symmetry. The position of ligating atoms in (V) may be approximated to a distorted trigonal bipyramid, which is a coordination geometry often observed in mixed-ligand zinc tri-tert-butoxysilanethiolates (Becker et al., 1996; Dołęga et al., 2004). Atoms O1 and O4 occupy the apical positions of the bipyramid and the O1—Zn1—O4 angle is close to 180°. The deviations from the least-squares equatorial plane are -0.0152 (3) for Zn1, 0.0055 (5) for S1, 0.0052 (5) for S2 and 0.0045 (18) Å for N1, with O1 and O4 distances of -2.3833 (16) and 2.3894 (16) Å, respectively. The methyl groups bound to C21 exhibit disorder, and it was necessary to refine them over two positions.

Complex (V) possesses a typically large (> 120°) S—Zn—S angle, as is always found in five-coordinated zinc–tri-tert-butoxysilanethiolates with ZnNO₂S₂ kernels (Becker et al., 1996; Dołęga et al., 2004, 2005). This angle becomes much smaller when the Zn coordination geometry approaches tetrahedral in complexes with ZnN₂S₂ or ZnNOS₂ coordination cores; indeed, it is this angle that shows the most pronounced difference among the greometric parameters of the title compounds (Becker, Dołęga et al., 2001; Dołęga et al., 2004, 2008; this work, Table 4).

We do not think that an additional, weak intramolecular O—H···S interaction between 2-hydroxymethylimidazole and tri-tert-butoxysilanethiolate observed here (Table 3) would enhance stability of (V) in solution. It is evident that the side chain must be extended to achieve chelation in the studied systems. The molecules in (V) pack in one-dimensional zigzag chains linked by N—H···O hydrogen bonds that are approximately parallel to the b axis (Fig. 4).

Related literature

For related literature, see: Barszcz (2005); Becker et al. (1996, 2002); Becker, Dołęga, Konitz, Swinder & Wojnowski (2001); Becker, Zalewska, Konitz & Wojnowski (2001); Dalosto et al., 2001; Dołęga & Walewski (2007); Dołęga et al. (2004, 2005, 2006, 2008); Dołęga, Baranowska, Gajda, Kaźmierski & Potrzebowski (2007); Garnuszek et al. (2002); Harding & Cole (1963); Hassanein & Hewaidy (1970); Horrocks et al. (1982); Kloskowska et al. (2006); Kropidłowska et al. (2007); Piękoś & Wojnowski (1962); Wojtczak et al., (1990).

S2. Experimental

Commercial histamine dihydrochloride (98%+, Alfa Aesar) and 4(5)-hydroxymethylimidazole (97%, Aldrich) were used. The synthesis of tri-tert-butoxysilanethiol was as described by Piękoś & Wojnowski (1962) and the synthesis of zinc acetyloacetonate was as described by Hassanein & Hewaidy (1970).

For the preparation of (III), triethylamine (2 mmol, 0.28 ml) was added to a Co^II chloride hexahydrate (0.5 mmol, 0.12 g) solution in 50 ml of water. Histamine dihydrochloride (2 mmol, 0.37 g) and neat tri-tert-butoxysilanethiol (1 mmol, 1.37 ml) were added to the resulting suspension. The reaction flask was closed with a rubber septum and the suspension was shaken vigorously for 20 min. A blue hydrophobic precipitate was collected, washed with water and dried in air. The dry solid was dissolved in methanol, the solution was filtered and the filtrate was left at 273–278 K. After a weekend, dark-blue crystals were collected [m.p. slow decomposition 403–423 K, black product melts at 456–458 K; yield 78% (crude product)].

Compound (IV) was synthesized in the same manner as (III). Zn^II chloride hexahydrate (0.5 mmol, 0.12 g) was used instead of Co^II chloride hexahydrate, and the resulting white, hydrophobic precipitate was recrystallized from methanol–acetonitrile mixture (80% v/v methanol) [m.p. 471–475 K with decomposition; yield 99% (crude product)].

For the preparation of (V), zinc acetyloacetonate (1 mmol, 0.27 g) and tri-tert-butoxysilanethiol (6 mmol, 0.9 ml) were suspended in 5 ml of methanol and warmed till dissolution. 4(5)-Hydroxyimidazole (1 mmol, 0.098 g) in 1 ml of methanol was added to the reaction mixture. Crystallization occurred immediately. Crystals were collected and recrystallized from a toluene/methanol mixture (50% v/v) (yield 87% of crude product).

S3. Refinement

The ^tBu groups attached to atom O6 are disordered over two orientations. In (III), the disordered atoms were set as isotropic. The site occupancies of the disordered groups are 0.641 (9) and 0.359 (9) in (III), 0.612 (17) and 0.388 (17) in (IV), and 0.65 (3) and 0.35 (3) in (V). H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.98 Å, N—H = 0.88–0.92 Å, O—H = 0.84 Å and U_iso(H) = 1.2U_eq(C,O,N), 1.3U_eq(C,N) [all methylene C and NH₂ in (IV)] or 1.5U_eq(C) (all methyl C).

There were missing reflections reported by PLATON in (III) and (IV). An inspection of the structure factors has revealed that the missing reflections are located either below Θ_min or above Θ = 19°. The calculated values of intensity for the missing reflections above Θ = 19° [13 for (III) and 19 for (IV)] indicate that their intensity is low or very low. Since the overall completeness of both measurements is above 99%, we assume that the missing reflections do not have a significant influence on the refinement results.

The most discrepant low-angle reflections (outliers) removed from the refinements were 100 for (III); 111 for (IV); and 111, 200, 110 and 112 for (V).

Computing details

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006). Program(s) used to solve structure: SHELXS86 (Sheldrick, 2008) for (III); SHELXS97 (Sheldrick, 2008) for (IV), (V). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of the molecule of (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All ^tBu H atoms have been omitted for clarity. Only the major conformation for the disordered methyl groups on C21 is shown. Hydrogen bonds are indicated with dashed lines.
	Fig. 2. The packing of (III). Displacement ellipsoids are drawn at the 30% probability level. All ^tBu H atoms have been omitted. Only the major conformations for the disordered methyl groups on C21 are shown. Hydrogen bonds are indicated with dashed lines. [Symmetry codes: (i) x + 1, y, z; (ii) -x + 1, -y + 1, -z + 1.] Don't match table
	Fig. 3. A view of the molecule of (V), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All ^tBu H atoms have been omitted for clarity. Only the major conformations for the disordered methyl groups on C21 are shown. Hydrogen bonds are indicated with dashed lines.
	Fig. 4. A view of the one-dimensional chains of molecules of (V) linked by hydrogen bonds. Displacement ellipsoids are drawn at the 30% probability level. All ^tBu groups have been omitted for clarity. Only the major conformation for the disordered methyl groups on C21 is shown. Hydrogen bonds are indicated with dashed lines. [Symmetry codes: (i) -x, y + 1/2, -z + 1/2.]

(III) [2-(1H-imidazol-4-yl-κN³)ethylamine-κ²N]bis(tri- tert-butoxysilanethiolato-κS)cobalt(II)

Crystal data

[Co(C12H27O3SSi)2(C5H9N3)]	Z = 2
Mr = 729.05	F(000) = 786
Triclinic, P1	Dx = 1.217 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2498 (4) Å	Cell parameters from 12335 reflections
b = 14.3000 (9) Å	θ = 2.3–32.5°
c = 16.0164 (11) Å	µ = 0.64 mm^−1
α = 95.190 (5)°	T = 120 K
β = 96.805 (4)°	Prism, blue
γ = 107.336 (4)°	0.16 × 0.10 × 0.06 mm
V = 1990.3 (2) Å^3

Data collection

Oxford Diffraction KM-4 CCD diffractometer	7381 independent reflections
Graphite monochromator	6248 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	Rint = 0.026
ω scans, 0.75 deg width	θmax = 25.5°, θmin = 2.4°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid [(1995). Acta Cryst. A51, 887-897]	h = −11→11
Tmin = 0.842, Tmax = 0.93	k = −16→17
13851 measured reflections	l = −19→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.0814P] where P = (Fo^2 + 2Fc^2)/3
7381 reflections	(Δ/σ)max = 0.001
407 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.3788 (2)	0.15877 (14)	0.11437 (12)	0.0265 (4)
C2	0.4409 (2)	0.25794 (16)	0.08301 (13)	0.0314 (5)
H2A	0.5461	0.2672	0.0724	0.047*
H2B	0.4401	0.3109	0.1261	0.047*
H2C	0.3765	0.2597	0.0303	0.047*
C3	0.4768 (2)	0.15259 (15)	0.19555 (13)	0.0326 (5)
H3A	0.4355	0.0876	0.2138	0.049*
H3B	0.4759	0.2042	0.24	0.049*
H3C	0.5822	0.162	0.1852	0.049*
C4	0.3713 (3)	0.07452 (18)	0.04676 (15)	0.0457 (6)
H4A	0.3308	0.0112	0.068	0.068*
H4B	0.4743	0.0814	0.0334	0.068*
H4C	0.3039	0.0768	−0.0046	0.068*
C5	−0.0738 (2)	0.07958 (13)	0.24616 (11)	0.0219 (4)
C6	−0.1115 (2)	0.13698 (14)	0.32097 (12)	0.0292 (4)
H6A	−0.0203	0.1918	0.3466	0.044*
H6B	−0.1442	0.0929	0.3633	0.044*
H6C	−0.1942	0.1631	0.3012	0.044*
C7	0.0538 (2)	0.03738 (15)	0.27501 (14)	0.0323 (5)
H7A	0.0785	0.0026	0.2258	0.048*
H7B	0.02	−0.0089	0.3155	0.048*
H7C	0.1449	0.0913	0.3023	0.048*
C8	−0.2145 (2)	−0.00252 (14)	0.20242 (13)	0.0309 (4)
H8A	−0.2922	0.026	0.1792	0.046*
H8B	−0.2557	−0.0463	0.2435	0.046*
H8C	−0.1868	−0.0404	0.1563	0.046*
C9	0.0014 (2)	0.26009 (14)	0.01681 (11)	0.0238 (4)
C10	0.0164 (2)	0.16796 (15)	−0.03108 (12)	0.0308 (5)
H10A	0.1233	0.1791	−0.0391	0.046*
H10B	−0.0489	0.1527	−0.0865	0.046*
H10C	−0.0156	0.1124	0.0014	0.046*
C11	0.0587 (3)	0.34908 (16)	−0.02986 (13)	0.0377 (5)
H11A	0.0498	0.4081	0.0026	0.057*
H11B	−0.0032	0.3373	−0.0861	0.057*
H11C	0.1662	0.359	−0.036	0.057*
C12	−0.1652 (2)	0.24452 (17)	0.02788 (13)	0.0339 (5)
H12A	−0.1746	0.3054	0.0568	0.051*
H12B	−0.1985	0.1906	0.0619	0.051*
H12C	−0.2296	0.2276	−0.0279	0.051*
C13	0.4944 (2)	0.63086 (14)	0.18349 (11)	0.0245 (4)
C14	0.3985 (3)	0.57563 (17)	0.09988 (13)	0.0365 (5)
H14A	0.3376	0.5094	0.1087	0.055*
H14B	0.4663	0.5702	0.0583	0.055*
H14C	0.33	0.6118	0.0788	0.055*
C15	0.5884 (2)	0.57052 (16)	0.22226 (13)	0.0323 (5)
H15A	0.6488	0.6066	0.2763	0.048*
H15B	0.6574	0.559	0.1834	0.048*
H15C	0.5197	0.507	0.2321	0.048*
C16	0.5967 (3)	0.73176 (15)	0.17099 (13)	0.0350 (5)
H16A	0.5336	0.7695	0.1463	0.053*
H16B	0.6686	0.7237	0.1327	0.053*
H16C	0.6541	0.7672	0.2259	0.053*
C17	0.6714 (2)	0.78619 (14)	0.45211 (12)	0.0268 (4)
C18	0.7561 (2)	0.71228 (17)	0.47151 (14)	0.0369 (5)
H18A	0.6824	0.6494	0.479	0.055*
H18B	0.83	0.7383	0.5237	0.055*
H18C	0.8104	0.7016	0.4244	0.055*
C19	0.7845 (3)	0.88428 (16)	0.44070 (14)	0.0432 (6)
H19A	0.8384	0.8743	0.3932	0.065*
H19B	0.8589	0.9102	0.4927	0.065*
H19C	0.7292	0.9315	0.4289	0.065*
C20	0.5800 (2)	0.80003 (17)	0.52218 (12)	0.0337 (5)
H20A	0.5258	0.8474	0.5087	0.051*
H20B	0.6496	0.8252	0.576	0.051*
H20C	0.5055	0.7365	0.5272	0.051*
C21	0.2262 (2)	0.79912 (14)	0.33877 (14)	0.0330 (5)
C22	0.0731 (3)	0.76010 (17)	0.28161 (16)	0.0557 (8)
H22A	0.0831	0.7208	0.2305	0.084*
H22B	0.0394	0.8156	0.2655	0.084*
H22C	−0.0026	0.7186	0.3118	0.084*
C23	0.1935 (5)	0.8467 (3)	0.4253 (2)	0.0251 (9)*	0.641 (9)
H23A	0.113	0.7977	0.447	0.038*	0.641 (9)
H23B	0.16	0.9041	0.4152	0.038*	0.641 (9)
H23C	0.2873	0.8676	0.4669	0.038*	0.641 (9)
C24	0.3594 (5)	0.8744 (3)	0.3101 (3)	0.0362 (12)*	0.641 (9)
H24A	0.4471	0.8959	0.3559	0.054*	0.641 (9)
H24B	0.3284	0.9316	0.296	0.054*	0.641 (9)
H24C	0.3883	0.8442	0.2599	0.054*	0.641 (9)
C23A	0.2342 (10)	0.8645 (6)	0.4088 (5)	0.039 (2)*	0.359 (9)
H23D	0.1781	0.8289	0.4505	0.059*	0.359 (9)
H23E	0.1884	0.9148	0.3918	0.059*	0.359 (9)
H23F	0.3416	0.8964	0.4339	0.059*	0.359 (9)
C24A	0.3136 (9)	0.8484 (6)	0.2677 (6)	0.043 (2)*	0.359 (9)
H24D	0.2825	0.906	0.2552	0.064*	0.359 (9)
H24E	0.2887	0.8005	0.2162	0.064*	0.359 (9)
H24F	0.4243	0.8693	0.2872	0.064*	0.359 (9)
C25	−0.0407 (2)	0.39194 (14)	0.45256 (12)	0.0268 (4)
H25	0.0356	0.3934	0.4984	0.032*
C26	−0.2614 (2)	0.38520 (15)	0.38122 (13)	0.0326 (5)
H26	−0.3658	0.3818	0.3675	0.039*
C27	−0.1579 (2)	0.39160 (13)	0.32665 (12)	0.0238 (4)
C28	−0.1789 (2)	0.39131 (14)	0.23306 (12)	0.0271 (4)
H28A	−0.2852	0.3902	0.2136	0.035*
H28B	−0.1658	0.33	0.2059	0.035*
C29	−0.0685 (2)	0.47959 (14)	0.20329 (13)	0.0264 (4)
H29A	−0.105	0.4835	0.1435	0.034*
H29B	−0.066	0.5411	0.2379	0.034*
N1	−0.01775 (17)	0.39683 (10)	0.37253 (9)	0.0211 (3)
N2	−0.18577 (19)	0.38466 (13)	0.45961 (11)	0.0332 (4)
H2	−0.2259	0.3803	0.5068	0.04*
N3	0.08812 (17)	0.47106 (11)	0.21059 (9)	0.0213 (3)
H3D	0.1542	0.5317	0.2047	0.026*
H3E	0.0903	0.4273	0.1653	0.026*
O1	0.22245 (14)	0.14213 (9)	0.12977 (8)	0.0222 (3)
O2	−0.03000 (14)	0.14633 (9)	0.18415 (8)	0.0220 (3)
O3	0.09578 (14)	0.28665 (9)	0.09992 (7)	0.0200 (3)
O4	0.38474 (14)	0.64547 (9)	0.23786 (7)	0.0202 (3)
O5	0.57292 (15)	0.75172 (9)	0.37099 (8)	0.0255 (3)
O6	0.26689 (16)	0.71306 (10)	0.36144 (9)	0.0311 (3)
Si1	0.13711 (5)	0.21651 (3)	0.16951 (3)	0.01754 (12)
S1	0.27562 (5)	0.30659 (3)	0.27643 (3)	0.02047 (11)
S2	0.37744 (5)	0.54534 (3)	0.40429 (3)	0.01957 (11)
Si2	0.40510 (6)	0.66934 (3)	0.34178 (3)	0.01830 (12)
Co1	0.17535 (3)	0.426332 (16)	0.320022 (14)	0.01759 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0191 (9)	0.0297 (10)	0.0308 (10)	0.0106 (8)	0.0040 (8)	−0.0062 (8)
C2	0.0212 (10)	0.0430 (12)	0.0301 (11)	0.0097 (9)	0.0062 (8)	0.0027 (9)
C3	0.0262 (10)	0.0325 (11)	0.0411 (12)	0.0154 (9)	0.0004 (9)	0.0007 (9)
C4	0.0324 (12)	0.0532 (15)	0.0498 (14)	0.0203 (11)	0.0047 (10)	−0.0232 (11)
C5	0.0234 (9)	0.0183 (9)	0.0232 (9)	0.0042 (8)	0.0039 (7)	0.0055 (7)
C6	0.0368 (12)	0.0245 (10)	0.0256 (10)	0.0063 (9)	0.0093 (9)	0.0044 (8)
C7	0.0315 (11)	0.0288 (11)	0.0392 (12)	0.0118 (9)	0.0029 (9)	0.0123 (9)
C8	0.0309 (11)	0.0220 (10)	0.0347 (11)	0.0017 (9)	0.0035 (9)	0.0019 (8)
C9	0.0250 (10)	0.0285 (10)	0.0163 (9)	0.0070 (8)	0.0009 (7)	0.0025 (7)
C10	0.0305 (11)	0.0332 (11)	0.0253 (10)	0.0096 (9)	−0.0024 (8)	−0.0041 (8)
C11	0.0503 (14)	0.0360 (12)	0.0210 (10)	0.0060 (11)	0.0009 (9)	0.0051 (9)
C12	0.0262 (11)	0.0510 (13)	0.0264 (10)	0.0169 (10)	0.0007 (8)	0.0029 (9)
C13	0.0258 (10)	0.0256 (10)	0.0211 (9)	0.0048 (8)	0.0102 (8)	0.0009 (7)
C14	0.0386 (12)	0.0415 (13)	0.0245 (10)	0.0060 (10)	0.0090 (9)	−0.0050 (9)
C15	0.0309 (11)	0.0381 (12)	0.0334 (11)	0.0156 (10)	0.0153 (9)	0.0030 (9)
C16	0.0401 (12)	0.0307 (11)	0.0312 (11)	0.0014 (10)	0.0182 (9)	0.0043 (9)
C17	0.0259 (10)	0.0253 (10)	0.0230 (10)	−0.0003 (8)	0.0024 (8)	0.0017 (8)
C18	0.0285 (11)	0.0399 (12)	0.0387 (12)	0.0093 (10)	0.0001 (9)	−0.0018 (9)
C19	0.0430 (13)	0.0342 (12)	0.0351 (12)	−0.0104 (10)	−0.0016 (10)	0.0019 (9)
C20	0.0330 (11)	0.0431 (13)	0.0221 (10)	0.0105 (10)	0.0002 (9)	−0.0011 (9)
C21	0.0353 (12)	0.0205 (10)	0.0516 (13)	0.0170 (9)	0.0146 (10)	0.0085 (9)
C22	0.088 (2)	0.0343 (13)	0.0420 (14)	0.0301 (14)	−0.0215 (14)	−0.0029 (10)
C25	0.0312 (11)	0.0222 (10)	0.0261 (10)	0.0052 (8)	0.0112 (8)	−0.0007 (8)
C26	0.0216 (10)	0.0316 (11)	0.0414 (12)	0.0039 (9)	0.0107 (9)	−0.0041 (9)
C27	0.0205 (9)	0.0160 (9)	0.0335 (10)	0.0029 (7)	0.0076 (8)	0.0008 (7)
C28	0.0199 (9)	0.0258 (10)	0.0337 (11)	0.0047 (8)	0.0030 (8)	0.0040 (8)
C29	0.0213 (10)	0.0247 (10)	0.0341 (11)	0.0079 (8)	0.0036 (8)	0.0070 (8)
N1	0.0246 (8)	0.0155 (7)	0.0239 (8)	0.0056 (6)	0.0090 (6)	0.0011 (6)
N2	0.0296 (9)	0.0336 (10)	0.0320 (9)	0.0004 (8)	0.0190 (8)	−0.0039 (7)
N3	0.0195 (8)	0.0199 (8)	0.0252 (8)	0.0059 (6)	0.0056 (6)	0.0039 (6)
O1	0.0176 (6)	0.0237 (7)	0.0246 (7)	0.0070 (5)	0.0035 (5)	−0.0031 (5)
O2	0.0192 (6)	0.0237 (7)	0.0238 (6)	0.0068 (5)	0.0036 (5)	0.0068 (5)
O3	0.0217 (6)	0.0216 (6)	0.0161 (6)	0.0063 (5)	0.0019 (5)	0.0022 (5)
O4	0.0197 (6)	0.0221 (6)	0.0195 (6)	0.0068 (5)	0.0052 (5)	0.0032 (5)
O5	0.0286 (7)	0.0229 (7)	0.0191 (6)	−0.0010 (6)	0.0044 (5)	0.0023 (5)
O6	0.0360 (8)	0.0247 (7)	0.0430 (8)	0.0171 (6)	0.0210 (7)	0.0117 (6)
Si1	0.0172 (2)	0.0182 (2)	0.0177 (2)	0.0066 (2)	0.00305 (19)	0.00090 (18)
S1	0.0211 (2)	0.0213 (2)	0.0194 (2)	0.00957 (18)	0.00054 (17)	−0.00205 (17)
S2	0.0218 (2)	0.0182 (2)	0.0187 (2)	0.00543 (18)	0.00431 (17)	0.00317 (17)
Si2	0.0204 (3)	0.0164 (2)	0.0189 (2)	0.0057 (2)	0.00666 (19)	0.00200 (18)
Co1	0.01831 (14)	0.01689 (14)	0.01882 (14)	0.00631 (10)	0.00581 (10)	0.00205 (9)

Geometric parameters (Å, º)

C1—O1	1.449 (2)	C18—H18C	0.98
C1—C2	1.518 (3)	C19—H19A	0.98
C1—C3	1.519 (3)	C19—H19B	0.98
C1—C4	1.525 (3)	C19—H19C	0.98
C2—H2A	0.98	C20—H20A	0.98
C2—H2B	0.98	C20—H20B	0.98
C2—H2C	0.98	C20—H20C	0.98
C3—H3A	0.98	C21—C23A	1.373 (8)
C3—H3B	0.98	C21—O6	1.453 (2)
C3—H3C	0.98	C21—C22	1.512 (3)
C4—H4A	0.98	C21—C24	1.523 (4)
C4—H4B	0.98	C21—C23	1.589 (4)
C4—H4C	0.98	C21—C24A	1.572 (7)
C5—O2	1.449 (2)	C22—H22A	0.98
C5—C8	1.512 (3)	C22—H22B	0.98
C5—C7	1.522 (3)	C22—H22C	0.98
C5—C6	1.524 (3)	C23—H23A	0.98
C6—H6A	0.98	C23—H23B	0.98
C6—H6B	0.98	C23—H23C	0.98
C6—H6C	0.98	C24—H24A	0.98
C7—H7A	0.98	C24—H24B	0.98
C7—H7B	0.98	C24—H24C	0.98
C7—H7C	0.98	C23A—H23D	0.98
C8—H8A	0.98	C23A—H23E	0.98
C8—H8B	0.98	C23A—H23F	0.98
C8—H8C	0.98	C24A—H24D	0.98
C9—O3	1.454 (2)	C24A—H24E	0.98
C9—C10	1.515 (3)	C24A—H24F	0.98
C9—C12	1.524 (3)	C25—N1	1.328 (2)
C9—C11	1.524 (3)	C25—N2	1.334 (3)
C10—H10A	0.98	C25—H25	0.95
C10—H10B	0.98	C26—C27	1.360 (3)
C10—H10C	0.98	C26—N2	1.365 (3)
C11—H11A	0.98	C26—H26	0.95
C11—H11B	0.98	C27—N1	1.390 (2)
C11—H11C	0.98	C27—C28	1.488 (3)
C12—H12A	0.98	C28—C29	1.523 (3)
C12—H12B	0.98	C28—H28A	0.99
C12—H12C	0.98	C28—H28B	0.99
C13—O4	1.461 (2)	C29—N3	1.481 (2)
C13—C15	1.517 (3)	C29—H29A	0.99
C13—C16	1.517 (3)	C29—H29B	0.99
C13—C14	1.521 (3)	N1—Co1	2.0116 (15)
C14—H14A	0.98	N2—H2	0.88
C14—H14B	0.98	N3—Co1	2.0754 (15)
C14—H14C	0.98	N3—H3D	0.92
C15—H15A	0.98	N3—H3E	0.92
C15—H15B	0.98	O1—Si1	1.6298 (13)
C15—H15C	0.98	O2—Si1	1.6295 (13)
C16—H16A	0.98	O3—Si1	1.6506 (12)
C16—H16B	0.98	O4—Si2	1.6453 (12)
C16—H16C	0.98	O5—Si2	1.6293 (13)
C17—O5	1.448 (2)	O6—Si2	1.6310 (14)
C17—C20	1.516 (3)	Si1—S1	2.0810 (7)
C17—C19	1.521 (3)	S1—Co1	2.2724 (5)
C17—C18	1.524 (3)	S2—Si2	2.0794 (6)
C18—H18A	0.98	S2—Co1	2.3028 (5)
C18—H18B	0.98
O1—C1—C2	110.90 (15)	C17—C19—H19A	109.5
O1—C1—C3	109.00 (16)	C17—C19—H19B	109.5
C2—C1—C3	111.12 (16)	H19A—C19—H19B	109.5
O1—C1—C4	105.32 (15)	C17—C19—H19C	109.5
C2—C1—C4	110.62 (18)	H19A—C19—H19C	109.5
C3—C1—C4	109.70 (17)	H19B—C19—H19C	109.5
C1—C2—H2A	109.5	C17—C20—H20A	109.5
C1—C2—H2B	109.5	C17—C20—H20B	109.5
H2A—C2—H2B	109.5	H20A—C20—H20B	109.5
C1—C2—H2C	109.5	C17—C20—H20C	109.5
H2A—C2—H2C	109.5	H20A—C20—H20C	109.5
H2B—C2—H2C	109.5	H20B—C20—H20C	109.5
C1—C3—H3A	109.5	C23A—C21—O6	112.2 (4)
C1—C3—H3B	109.5	C23A—C21—C22	116.1 (4)
H3A—C3—H3B	109.5	O6—C21—C22	106.32 (17)
C1—C3—H3C	109.5	C23A—C21—C24	90.4 (4)
H3A—C3—H3C	109.5	O6—C21—C24	111.66 (19)
H3B—C3—H3C	109.5	C22—C21—C24	119.8 (3)
C1—C4—H4A	109.5	O6—C21—C23	103.83 (19)
C1—C4—H4B	109.5	C22—C21—C23	105.8 (2)
H4A—C4—H4B	109.5	C24—C21—C23	108.2 (2)
C1—C4—H4C	109.5	C23A—C21—C24A	113.8 (5)
H4A—C4—H4C	109.5	O6—C21—C24A	113.0 (3)
H4B—C4—H4C	109.5	C22—C21—C24A	94.0 (4)
O2—C5—C8	106.03 (14)	C23—C21—C24A	130.9 (3)
O2—C5—C7	111.20 (15)	C21—C22—H22A	109.5
C8—C5—C7	110.13 (16)	C21—C22—H22B	109.5
O2—C5—C6	107.83 (14)	H22A—C22—H22B	109.5
C8—C5—C6	110.78 (16)	C21—C22—H22C	109.5
C7—C5—C6	110.74 (16)	H22A—C22—H22C	109.5
C5—C6—H6A	109.5	H22B—C22—H22C	109.5
C5—C6—H6B	109.5	C21—C23—H23A	109.5
H6A—C6—H6B	109.5	C21—C23—H23B	109.5
C5—C6—H6C	109.5	C21—C23—H23C	109.5
H6A—C6—H6C	109.5	C21—C24—H24A	109.5
H6B—C6—H6C	109.5	C21—C24—H24B	109.5
C5—C7—H7A	109.5	C21—C24—H24C	109.5
C5—C7—H7B	109.5	C21—C23A—H23D	109.5
H7A—C7—H7B	109.5	C21—C23A—H23E	109.5
C5—C7—H7C	109.5	H23D—C23A—H23E	109.5
H7A—C7—H7C	109.5	C21—C23A—H23F	109.5
H7B—C7—H7C	109.5	H23D—C23A—H23F	109.5
C5—C8—H8A	109.5	H23E—C23A—H23F	109.5
C5—C8—H8B	109.5	C21—C24A—H24D	109.5
H8A—C8—H8B	109.5	C21—C24A—H24E	109.5
C5—C8—H8C	109.5	H24D—C24A—H24E	109.5
H8A—C8—H8C	109.5	C21—C24A—H24F	109.5
H8B—C8—H8C	109.5	H24D—C24A—H24F	109.5
O3—C9—C10	112.16 (15)	H24E—C24A—H24F	109.5
O3—C9—C12	108.85 (15)	N1—C25—N2	110.52 (18)
C10—C9—C12	110.00 (17)	N1—C25—H25	124.7
O3—C9—C11	105.01 (15)	N2—C25—H25	124.7
C10—C9—C11	110.67 (16)	C27—C26—N2	106.45 (18)
C12—C9—C11	110.04 (17)	C27—C26—H26	126.8
C9—C10—H10A	109.5	N2—C26—H26	126.8
C9—C10—H10B	109.5	C26—C27—N1	108.50 (17)
H10A—C10—H10B	109.5	C26—C27—C28	129.68 (18)
C9—C10—H10C	109.5	N1—C27—C28	121.81 (16)
H10A—C10—H10C	109.5	C27—C28—C29	114.13 (16)
H10B—C10—H10C	109.5	C27—C28—H28A	108.7
C9—C11—H11A	109.5	C29—C28—H28A	108.7
C9—C11—H11B	109.5	C27—C28—H28B	108.7
H11A—C11—H11B	109.5	C29—C28—H28B	108.7
C9—C11—H11C	109.5	H28A—C28—H28B	107.6
H11A—C11—H11C	109.5	N3—C29—C28	111.08 (15)
H11B—C11—H11C	109.5	N3—C29—H29A	109.4
C9—C12—H12A	109.5	C28—C29—H29A	109.4
C9—C12—H12B	109.5	N3—C29—H29B	109.4
H12A—C12—H12B	109.5	C28—C29—H29B	109.4
C9—C12—H12C	109.5	H29A—C29—H29B	108
H12A—C12—H12C	109.5	C25—N1—C27	106.07 (16)
H12B—C12—H12C	109.5	C25—N1—Co1	131.45 (14)
O4—C13—C15	111.03 (14)	C27—N1—Co1	121.89 (12)
O4—C13—C16	108.08 (15)	C25—N2—C26	108.44 (16)
C15—C13—C16	110.94 (17)	C25—N2—H2	125.8
O4—C13—C14	105.59 (15)	C26—N2—H2	125.8
C15—C13—C14	110.32 (17)	C29—N3—Co1	118.59 (11)
C16—C13—C14	110.74 (16)	C29—N3—H3D	107.7
C13—C14—H14A	109.5	Co1—N3—H3D	107.7
C13—C14—H14B	109.5	C29—N3—H3E	107.7
H14A—C14—H14B	109.5	Co1—N3—H3E	107.7
C13—C14—H14C	109.5	H3D—N3—H3E	107.1
H14A—C14—H14C	109.5	C1—O1—Si1	131.67 (11)
H14B—C14—H14C	109.5	C5—O2—Si1	131.36 (11)
C13—C15—H15A	109.5	C9—O3—Si1	130.58 (11)
C13—C15—H15B	109.5	C13—O4—Si2	129.95 (11)
H15A—C15—H15B	109.5	C17—O5—Si2	132.89 (11)
C13—C15—H15C	109.5	C21—O6—Si2	133.08 (12)
H15A—C15—H15C	109.5	O1—Si1—O2	105.95 (7)
H15B—C15—H15C	109.5	O1—Si1—O3	111.60 (7)
C13—C16—H16A	109.5	O2—Si1—O3	103.88 (6)
C13—C16—H16B	109.5	O1—Si1—S1	110.19 (5)
H16A—C16—H16B	109.5	O2—Si1—S1	116.05 (5)
C13—C16—H16C	109.5	O3—Si1—S1	109.06 (5)
H16A—C16—H16C	109.5	Si1—S1—Co1	110.43 (2)
H16B—C16—H16C	109.5	Si2—S2—Co1	103.84 (2)
O5—C17—C20	111.17 (16)	O5—Si2—O6	111.83 (7)
O5—C17—C19	105.13 (15)	O5—Si2—O4	106.04 (6)
C20—C17—C19	110.77 (18)	O6—Si2—O4	105.85 (7)
O5—C17—C18	109.16 (16)	O5—Si2—S2	112.73 (5)
C20—C17—C18	110.44 (17)	O6—Si2—S2	106.07 (5)
C19—C17—C18	110.05 (18)	O4—Si2—S2	114.20 (5)
C17—C18—H18A	109.5	N1—Co1—N3	96.46 (6)
C17—C18—H18B	109.5	N1—Co1—S1	122.45 (4)
H18A—C18—H18B	109.5	N3—Co1—S1	106.17 (4)
C17—C18—H18C	109.5	N1—Co1—S2	112.32 (4)
H18A—C18—H18C	109.5	N3—Co1—S2	115.05 (4)
H18B—C18—H18C	109.5	S1—Co1—S2	104.567 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2^i	0.88	2.49	3.2365 (16)	143
N2—H2···O6^i	0.88	2.60	3.367 (2)	146
N3—H3D···O4	0.92	2.23	3.0626 (19)	150
N3—H3E···O3	0.92	2.2	3.0654 (19)	157

Symmetry code: (i) −x, −y+1, −z+1.

(IV) [2-(1H-imidazol-4-yl-κN³)ethylamine-κ²N]bis(tri- tert-butoxysilanethiolato-κS)zinc(II)

Crystal data

[Zn(C12H27O3SSi)2(C5H9N3)]	Z = 2
Mr = 735.49	F(000) = 792
Triclinic, P1	Dx = 1.227 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2535 (3) Å	Cell parameters from 14894 reflections
b = 14.3163 (5) Å	θ = 2.1–32.3°
c = 15.9899 (6) Å	µ = 0.82 mm^−1
α = 95.086 (3)°	T = 120 K
β = 96.805 (3)°	Prism, colourless
γ = 107.337 (3)°	0.21 × 0.15 × 0.09 mm
V = 1990.55 (12) Å^3

Data collection

Oxford Diffraction KM-4 CCD diffractometer	7386 independent reflections
Graphite monochromator	6730 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	Rint = 0.021
ω scans, 0.75 deg width	θmax = 25.5°, θmin = 2.4°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid [(1995). Acta Cryst. A51, 887-897].	h = −10→11
Tmin = 0.79, Tmax = 0.857	k = −17→17
13696 measured reflections	l = −19→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.3294P] where P = (Fo^2 + 2Fc^2)/3
7386 reflections	(Δ/σ)max = 0.001
427 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.37862 (18)	0.15906 (13)	0.11451 (11)	0.0262 (4)
C2	0.4761 (2)	0.15242 (14)	0.19562 (12)	0.0324 (4)
H2A	0.4779	0.2051	0.2397	0.049*
H2B	0.5807	0.1597	0.1848	0.049*
H2C	0.4327	0.0882	0.2148	0.049*
C3	0.44174 (19)	0.25839 (14)	0.08313 (12)	0.0319 (4)
H3A	0.3773	0.2607	0.0306	0.048*
H3B	0.5466	0.2671	0.0722	0.048*
H3C	0.4419	0.3113	0.1264	0.048*
C4	0.3701 (2)	0.07517 (17)	0.04610 (14)	0.0461 (5)
H4A	0.3276	0.0117	0.0667	0.069*
H4B	0.4731	0.0812	0.0331	0.069*
H4C	0.304	0.0788	−0.0054	0.069*
C5	0.00302 (19)	0.26218 (12)	0.01727 (10)	0.0233 (3)
C6	0.0175 (2)	0.16974 (13)	−0.03073 (11)	0.0303 (4)
H6A	0.1245	0.1805	−0.0384	0.045*
H6B	−0.0472	0.155	−0.0864	0.045*
H6C	−0.0154	0.1142	0.0017	0.045*
C7	0.0615 (2)	0.35093 (14)	−0.02938 (11)	0.0369 (4)
H7A	0.0545	0.4102	0.0034	0.055*
H7B	−0.0008	0.3399	−0.0855	0.055*
H7C	0.1685	0.3598	−0.0361	0.055*
C8	−0.1633 (2)	0.24701 (16)	0.02817 (12)	0.0343 (4)
H8A	−0.1967	0.1936	0.0627	0.051*
H8B	−0.2276	0.2296	−0.0277	0.051*
H8C	−0.1727	0.308	0.0565	0.051*
C9	−0.07397 (18)	0.08058 (11)	0.24590 (10)	0.0216 (3)
C10	−0.2151 (2)	−0.00135 (13)	0.20138 (12)	0.0312 (4)
H10A	−0.293	0.0273	0.1789	0.047*
H10B	−0.2559	−0.046	0.242	0.047*
H10C	−0.1873	−0.0382	0.1546	0.047*
C11	0.0530 (2)	0.03816 (14)	0.27478 (13)	0.0332 (4)
H11A	0.0786	0.0042	0.2254	0.05*
H11B	0.0185	−0.0088	0.3148	0.05*
H11C	0.1438	0.0917	0.3027	0.05*
C12	−0.1123 (2)	0.13729 (12)	0.32074 (11)	0.0291 (4)
H12A	−0.022	0.1928	0.346	0.044*
H12B	−0.1434	0.0933	0.3634	0.044*
H12C	−0.1964	0.1623	0.301	0.044*
C13	0.49693 (19)	0.63110 (12)	0.18555 (10)	0.0239 (3)
C14	0.4033 (2)	0.57499 (15)	0.10159 (11)	0.0363 (4)
H14A	0.3424	0.5089	0.1107	0.055*
H14B	0.4723	0.5693	0.0608	0.055*
H14C	0.3348	0.6106	0.0792	0.055*
C15	0.5912 (2)	0.57143 (14)	0.22552 (12)	0.0326 (4)
H15A	0.6503	0.6078	0.2798	0.049*
H15B	0.6613	0.5602	0.1873	0.049*
H15C	0.5227	0.5078	0.2353	0.049*
C16	0.5993 (2)	0.73228 (13)	0.17283 (12)	0.0356 (4)
H16A	0.5363	0.7692	0.1466	0.053*
H16B	0.6731	0.7244	0.1358	0.053*
H16C	0.6544	0.7685	0.228	0.053*
C17	0.66838 (19)	0.79047 (12)	0.45315 (10)	0.0265 (4)
C18	0.7554 (2)	0.71781 (15)	0.47269 (13)	0.0373 (4)
H18A	0.6829	0.6546	0.4804	0.056*
H18B	0.8292	0.7443	0.5248	0.056*
H18C	0.8099	0.7078	0.4255	0.056*
C19	0.7801 (3)	0.88895 (15)	0.44128 (13)	0.0445 (5)
H19A	0.8347	0.8793	0.394	0.067*
H19B	0.8539	0.9156	0.4934	0.067*
H19C	0.7235	0.9353	0.4288	0.067*
C20	0.5768 (2)	0.80362 (15)	0.52365 (11)	0.0333 (4)
H20A	0.5244	0.8521	0.5111	0.05*
H20B	0.6461	0.8269	0.5777	0.05*
H20C	0.5009	0.7403	0.5276	0.05*
C21	0.2219 (2)	0.79809 (13)	0.33632 (13)	0.0342 (4)
C22	0.0666 (3)	0.75888 (16)	0.28195 (15)	0.0565 (7)
H22A	0.0741	0.7207	0.2296	0.085*
H22B	0.0305	0.8142	0.2677	0.085*
H22C	−0.0059	0.7163	0.3132	0.085*
C23	0.3540 (9)	0.8728 (4)	0.3074 (6)	0.0454 (17)	0.612 (17)
H23A	0.442	0.894	0.353	0.068*	0.612 (17)
H23B	0.3231	0.9301	0.2935	0.068*	0.612 (17)
H23C	0.3822	0.8427	0.2569	0.068*	0.612 (17)
C24	0.1935 (11)	0.8492 (9)	0.4232 (7)	0.0343 (14)	0.612 (17)
H24A	0.1159	0.8012	0.4477	0.051*	0.612 (17)
H24B	0.1578	0.9054	0.4119	0.051*	0.612 (17)
H24C	0.2895	0.8722	0.4633	0.051*	0.612 (17)
C23A	0.3059 (11)	0.8431 (9)	0.2585 (12)	0.053 (3)	0.388 (17)
H23D	0.4172	0.8648	0.2758	0.079*	0.388 (17)
H23E	0.2732	0.8994	0.2437	0.079*	0.388 (17)
H23F	0.2779	0.7922	0.209	0.079*	0.388 (17)
C24A	0.233 (2)	0.8623 (14)	0.4069 (11)	0.056 (4)	0.388 (17)
H24D	0.1766	0.8265	0.4486	0.084*	0.388 (17)
H24E	0.1883	0.9137	0.3911	0.084*	0.388 (17)
H24F	0.3405	0.8928	0.4316	0.084*	0.388 (17)
C25	−0.0325 (2)	0.39171 (12)	0.45325 (11)	0.0266 (4)
H25	0.0452	0.3946	0.4988	0.032*
C26	−0.2556 (2)	0.38211 (13)	0.38281 (12)	0.0333 (4)
H26	−0.3605	0.3777	0.3696	0.04*
C27	−0.15301 (18)	0.38960 (11)	0.32763 (11)	0.0239 (3)
C28	−0.17608 (18)	0.38940 (12)	0.23392 (11)	0.0268 (4)
H28A	−0.2832	0.3868	0.2149	0.035*
H28B	−0.1611	0.3289	0.2064	0.035*
C29	−0.06848 (18)	0.47907 (12)	0.20409 (11)	0.0259 (4)
H29A	−0.1066	0.4833	0.1445	0.034*
H29B	−0.0673	0.5398	0.2394	0.034*
N1	−0.01195 (15)	0.39653 (9)	0.37287 (8)	0.0203 (3)
N2	−0.17823 (17)	0.38222 (11)	0.46097 (10)	0.0339 (4)
H2	−0.2176	0.3769	0.5085	0.041*
N3	0.08939 (15)	0.47270 (10)	0.21009 (8)	0.0205 (3)
H3D	0.1532	0.5337	0.2035	0.027*
H3E	0.0916	0.4293	0.1646	0.027*
O1	0.22235 (12)	0.14306 (8)	0.12960 (7)	0.0221 (2)
O2	0.09709 (12)	0.28836 (8)	0.10056 (7)	0.0195 (2)
O3	−0.02970 (12)	0.14760 (8)	0.18413 (7)	0.0213 (2)
O4	0.38640 (12)	0.64553 (8)	0.23892 (7)	0.0195 (2)
O5	0.57009 (13)	0.75507 (8)	0.37208 (7)	0.0256 (3)
O6	0.26328 (14)	0.71277 (9)	0.35991 (8)	0.0316 (3)
Si1	0.13785 (5)	0.21774 (3)	0.17001 (3)	0.01689 (10)
Si2	0.40432 (5)	0.67100 (3)	0.34264 (3)	0.01777 (10)
S1	0.27735 (4)	0.30608 (3)	0.27709 (2)	0.01976 (9)
S2	0.37927 (4)	0.54869 (3)	0.40704 (2)	0.01889 (9)
Zn1	0.183032 (19)	0.429801 (12)	0.319338 (10)	0.01723 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0193 (8)	0.0309 (9)	0.0294 (9)	0.0124 (7)	0.0037 (7)	−0.0066 (7)
C2	0.0269 (9)	0.0333 (9)	0.0397 (10)	0.0168 (8)	0.0001 (8)	−0.0006 (8)
C3	0.0200 (8)	0.0454 (11)	0.0318 (9)	0.0109 (8)	0.0075 (7)	0.0049 (8)
C4	0.0347 (11)	0.0530 (13)	0.0500 (12)	0.0218 (10)	0.0043 (9)	−0.0228 (10)
C5	0.0249 (8)	0.0278 (8)	0.0165 (7)	0.0080 (7)	0.0009 (6)	0.0033 (6)
C6	0.0301 (9)	0.0327 (9)	0.0251 (9)	0.0096 (7)	−0.0015 (7)	−0.0037 (7)
C7	0.0506 (12)	0.0337 (10)	0.0217 (9)	0.0062 (9)	0.0021 (8)	0.0068 (8)
C8	0.0258 (9)	0.0512 (11)	0.0281 (9)	0.0168 (8)	0.0004 (7)	0.0051 (8)
C9	0.0221 (8)	0.0177 (7)	0.0250 (8)	0.0046 (6)	0.0043 (6)	0.0072 (6)
C10	0.0299 (9)	0.0231 (8)	0.0349 (10)	0.0018 (7)	0.0017 (8)	0.0014 (7)
C11	0.0319 (10)	0.0292 (9)	0.0417 (11)	0.0120 (8)	0.0038 (8)	0.0154 (8)
C12	0.0388 (10)	0.0221 (8)	0.0255 (9)	0.0057 (7)	0.0101 (7)	0.0052 (7)
C13	0.0254 (8)	0.0258 (8)	0.0199 (8)	0.0048 (7)	0.0108 (6)	0.0017 (6)
C14	0.0378 (10)	0.0410 (11)	0.0243 (9)	0.0046 (8)	0.0087 (8)	−0.0054 (8)
C15	0.0287 (9)	0.0395 (10)	0.0367 (10)	0.0174 (8)	0.0153 (8)	0.0048 (8)
C16	0.0423 (11)	0.0301 (9)	0.0310 (10)	0.0006 (8)	0.0198 (8)	0.0049 (8)
C17	0.0267 (8)	0.0251 (8)	0.0216 (8)	−0.0003 (7)	0.0026 (7)	0.0011 (7)
C18	0.0273 (9)	0.0400 (11)	0.0403 (11)	0.0080 (8)	−0.0005 (8)	−0.0016 (9)
C19	0.0483 (12)	0.0331 (10)	0.0332 (10)	−0.0124 (9)	0.0000 (9)	0.0020 (8)
C20	0.0328 (10)	0.0427 (11)	0.0223 (8)	0.0111 (8)	0.0014 (7)	−0.0004 (8)
C21	0.0367 (10)	0.0212 (8)	0.0541 (12)	0.0181 (8)	0.0163 (9)	0.0099 (8)
C22	0.0881 (19)	0.0347 (11)	0.0428 (12)	0.0279 (12)	−0.0223 (12)	−0.0023 (10)
C23	0.060 (3)	0.035 (2)	0.061 (4)	0.029 (2)	0.031 (3)	0.029 (3)
C24	0.037 (3)	0.034 (2)	0.036 (3)	0.020 (2)	0.004 (2)	−0.0056 (19)
C23A	0.042 (4)	0.047 (4)	0.086 (9)	0.024 (3)	0.021 (5)	0.045 (5)
C24A	0.073 (10)	0.044 (7)	0.054 (9)	0.045 (7)	−0.028 (6)	−0.018 (5)
C25	0.0305 (9)	0.0207 (8)	0.0280 (9)	0.0046 (7)	0.0124 (7)	0.0007 (7)
C26	0.0224 (9)	0.0313 (9)	0.0433 (11)	0.0031 (7)	0.0135 (8)	−0.0036 (8)
C27	0.0202 (8)	0.0158 (7)	0.0345 (9)	0.0030 (6)	0.0077 (7)	0.0013 (7)
C28	0.0187 (8)	0.0252 (8)	0.0347 (9)	0.0043 (7)	0.0032 (7)	0.0049 (7)
C29	0.0206 (8)	0.0246 (8)	0.0346 (9)	0.0087 (7)	0.0039 (7)	0.0098 (7)
N1	0.0223 (7)	0.0149 (6)	0.0243 (7)	0.0048 (5)	0.0097 (5)	0.0019 (5)
N2	0.0314 (8)	0.0336 (8)	0.0328 (8)	0.0004 (7)	0.0207 (7)	−0.0038 (7)
N3	0.0197 (7)	0.0189 (6)	0.0234 (7)	0.0057 (5)	0.0043 (5)	0.0049 (5)
O1	0.0182 (5)	0.0224 (5)	0.0252 (6)	0.0076 (4)	0.0032 (4)	−0.0033 (5)
O2	0.0210 (5)	0.0212 (5)	0.0168 (5)	0.0072 (4)	0.0025 (4)	0.0028 (4)
O3	0.0192 (5)	0.0222 (6)	0.0236 (6)	0.0061 (4)	0.0041 (4)	0.0082 (5)
O4	0.0202 (5)	0.0200 (5)	0.0190 (5)	0.0060 (4)	0.0057 (4)	0.0040 (4)
O5	0.0297 (6)	0.0216 (6)	0.0193 (6)	−0.0019 (5)	0.0047 (5)	0.0027 (5)
O6	0.0359 (7)	0.0229 (6)	0.0481 (8)	0.0179 (5)	0.0245 (6)	0.0141 (5)
Si1	0.0165 (2)	0.0173 (2)	0.0179 (2)	0.00677 (16)	0.00326 (16)	0.00172 (16)
Si2	0.0204 (2)	0.0152 (2)	0.0190 (2)	0.00560 (17)	0.00774 (16)	0.00249 (16)
S1	0.0209 (2)	0.02000 (19)	0.01943 (19)	0.00990 (15)	0.00085 (15)	−0.00110 (15)
S2	0.02169 (19)	0.01690 (18)	0.01846 (19)	0.00549 (15)	0.00487 (15)	0.00369 (14)
Zn1	0.01840 (11)	0.01617 (10)	0.01894 (11)	0.00653 (7)	0.00625 (7)	0.00335 (7)

Geometric parameters (Å, º)

C1—O1	1.4480 (19)	C18—H18C	0.98
C1—C2	1.517 (2)	C19—H19A	0.98
C1—C3	1.522 (3)	C19—H19B	0.98
C1—C4	1.528 (2)	C19—H19C	0.98
C2—H2A	0.98	C20—H20A	0.98
C2—H2B	0.98	C20—H20B	0.98
C2—H2C	0.98	C20—H20C	0.98
C3—H3A	0.98	C21—C24A	1.365 (18)
C3—H3B	0.98	C21—O6	1.451 (2)
C3—H3C	0.98	C21—C22	1.508 (3)
C4—H4A	0.98	C21—C23	1.515 (5)
C4—H4B	0.98	C21—C24	1.598 (10)
C4—H4C	0.98	C21—C23A	1.625 (11)
C5—O2	1.4541 (18)	C22—H22A	0.98
C5—C6	1.519 (2)	C22—H22B	0.98
C5—C8	1.522 (2)	C22—H22C	0.98
C5—C7	1.522 (2)	C23—H23A	0.98
C6—H6A	0.98	C23—H23B	0.98
C6—H6B	0.98	C23—H23C	0.98
C6—H6C	0.98	C24—H24A	0.98
C7—H7A	0.98	C24—H24B	0.98
C7—H7B	0.98	C24—H24C	0.98
C7—H7C	0.98	C23A—H23D	0.98
C8—H8A	0.98	C23A—H23E	0.98
C8—H8B	0.98	C23A—H23F	0.98
C8—H8C	0.98	C24A—H24D	0.98
C9—O3	1.4469 (18)	C24A—H24E	0.98
C9—C10	1.519 (2)	C24A—H24F	0.98
C9—C11	1.520 (2)	C25—N1	1.326 (2)
C9—C12	1.522 (2)	C25—N2	1.336 (2)
C10—H10A	0.98	C25—H25	0.95
C10—H10B	0.98	C26—C27	1.359 (2)
C10—H10C	0.98	C26—N2	1.364 (3)
C11—H11A	0.98	C26—H26	0.95
C11—H11B	0.98	C27—N1	1.387 (2)
C11—H11C	0.98	C27—C28	1.488 (2)
C12—H12A	0.98	C28—C29	1.525 (2)
C12—H12B	0.98	C28—H28A	0.99
C12—H12C	0.98	C28—H28B	0.99
C13—O4	1.4555 (18)	C29—N3	1.483 (2)
C13—C15	1.519 (2)	C29—H29A	0.99
C13—C16	1.522 (2)	C29—H29B	0.99
C13—C14	1.522 (2)	N1—Zn1	2.0350 (13)
C14—H14A	0.98	N2—H2	0.88
C14—H14B	0.98	N3—Zn1	2.0804 (13)
C14—H14C	0.98	N3—H3D	0.92
C15—H15A	0.98	N3—H3E	0.92
C15—H15B	0.98	O1—Si1	1.6333 (11)
C15—H15C	0.98	O2—Si1	1.6507 (11)
C16—H16A	0.98	O3—Si1	1.6305 (11)
C16—H16B	0.98	O4—Si2	1.6441 (11)
C16—H16C	0.98	O5—Si2	1.6282 (12)
C17—O5	1.447 (2)	O6—Si2	1.6304 (12)
C17—C20	1.519 (2)	Si1—S1	2.0776 (6)
C17—C19	1.522 (2)	Si2—S2	2.0771 (6)
C17—C18	1.525 (3)	S1—Zn1	2.2813 (4)
C18—H18A	0.98	S2—Zn1	2.3005 (4)
C18—H18B	0.98
O1—C1—C2	109.26 (14)	C17—C19—H19A	109.5
O1—C1—C3	110.79 (13)	C17—C19—H19B	109.5
C2—C1—C3	111.04 (14)	H19A—C19—H19B	109.5
O1—C1—C4	105.16 (14)	C17—C19—H19C	109.5
C2—C1—C4	110.12 (15)	H19A—C19—H19C	109.5
C3—C1—C4	110.30 (16)	H19B—C19—H19C	109.5
C1—C2—H2A	109.5	C17—C20—H20A	109.5
C1—C2—H2B	109.5	C17—C20—H20B	109.5
H2A—C2—H2B	109.5	H20A—C20—H20B	109.5
C1—C2—H2C	109.5	C17—C20—H20C	109.5
H2A—C2—H2C	109.5	H20A—C20—H20C	109.5
H2B—C2—H2C	109.5	H20B—C20—H20C	109.5
C1—C3—H3A	109.5	C24A—C21—O6	110.5 (8)
C1—C3—H3B	109.5	C24A—C21—C22	115.9 (8)
H3A—C3—H3B	109.5	O6—C21—C22	106.55 (15)
C1—C3—H3C	109.5	C24A—C21—C23	90.3 (8)
H3A—C3—H3C	109.5	O6—C21—C23	111.6 (2)
H3B—C3—H3C	109.5	C22—C21—C23	121.3 (4)
C1—C4—H4A	109.5	O6—C21—C24	104.3 (5)
C1—C4—H4B	109.5	C22—C21—C24	105.3 (4)
H4A—C4—H4B	109.5	C23—C21—C24	106.3 (5)
C1—C4—H4C	109.5	C24A—C21—C23A	117.4 (7)
H4A—C4—H4C	109.5	O6—C21—C23A	112.0 (3)
H4B—C4—H4C	109.5	C22—C21—C23A	93.2 (6)
O2—C5—C6	112.16 (13)	C24—C21—C23A	132.2 (6)
O2—C5—C8	108.87 (13)	C21—C22—H22A	109.5
C6—C5—C8	109.92 (14)	C21—C22—H22B	109.5
O2—C5—C7	104.91 (13)	H22A—C22—H22B	109.5
C6—C5—C7	110.59 (14)	C21—C22—H22C	109.5
C8—C5—C7	110.27 (15)	H22A—C22—H22C	109.5
C5—C6—H6A	109.5	H22B—C22—H22C	109.5
C5—C6—H6B	109.5	C21—C23—H23A	109.5
H6A—C6—H6B	109.5	C21—C23—H23B	109.5
C5—C6—H6C	109.5	C21—C23—H23C	109.5
H6A—C6—H6C	109.5	C21—C24—H24A	109.5
H6B—C6—H6C	109.5	C21—C24—H24B	109.5
C5—C7—H7A	109.5	C21—C24—H24C	109.5
C5—C7—H7B	109.5	C21—C23A—H23D	109.5
H7A—C7—H7B	109.5	C21—C23A—H23E	109.5
C5—C7—H7C	109.5	H23D—C23A—H23E	109.5
H7A—C7—H7C	109.5	C21—C23A—H23F	109.5
H7B—C7—H7C	109.5	H23D—C23A—H23F	109.5
C5—C8—H8A	109.5	H23E—C23A—H23F	109.5
C5—C8—H8B	109.5	C21—C24A—H24D	109.5
H8A—C8—H8B	109.5	C21—C24A—H24E	109.5
C5—C8—H8C	109.5	H24D—C24A—H24E	109.5
H8A—C8—H8C	109.5	C21—C24A—H24F	109.5
H8B—C8—H8C	109.5	H24D—C24A—H24F	109.5
O3—C9—C10	105.88 (13)	H24E—C24A—H24F	109.5
O3—C9—C11	111.24 (13)	N1—C25—N2	110.26 (16)
C10—C9—C11	110.17 (14)	N1—C25—H25	124.9
O3—C9—C12	107.89 (12)	N2—C25—H25	124.9
C10—C9—C12	110.72 (14)	C27—C26—N2	106.40 (16)
C11—C9—C12	110.82 (15)	C27—C26—H26	126.8
C9—C10—H10A	109.5	N2—C26—H26	126.8
C9—C10—H10B	109.5	C26—C27—N1	108.50 (16)
H10A—C10—H10B	109.5	C26—C27—C28	129.54 (16)
C9—C10—H10C	109.5	N1—C27—C28	121.95 (14)
H10A—C10—H10C	109.5	C27—C28—C29	113.81 (14)
H10B—C10—H10C	109.5	C27—C28—H28A	108.8
C9—C11—H11A	109.5	C29—C28—H28A	108.8
C9—C11—H11B	109.5	C27—C28—H28B	108.8
H11A—C11—H11B	109.5	C29—C28—H28B	108.8
C9—C11—H11C	109.5	H28A—C28—H28B	107.7
H11A—C11—H11C	109.5	N3—C29—C28	111.16 (13)
H11B—C11—H11C	109.5	N3—C29—H29A	109.4
C9—C12—H12A	109.5	C28—C29—H29A	109.4
C9—C12—H12B	109.5	N3—C29—H29B	109.4
H12A—C12—H12B	109.5	C28—C29—H29B	109.4
C9—C12—H12C	109.5	H29A—C29—H29B	108
H12A—C12—H12C	109.5	C25—N1—C27	106.35 (14)
H12B—C12—H12C	109.5	C25—N1—Zn1	130.86 (12)
O4—C13—C15	111.07 (13)	C27—N1—Zn1	122.09 (11)
O4—C13—C16	108.04 (13)	C25—N2—C26	108.48 (14)
C15—C13—C16	110.90 (15)	C25—N2—H2	125.8
O4—C13—C14	105.89 (13)	C26—N2—H2	125.8
C15—C13—C14	110.01 (15)	C29—N3—Zn1	118.82 (10)
C16—C13—C14	110.81 (15)	C29—N3—H3D	107.6
C13—C14—H14A	109.5	Zn1—N3—H3D	107.6
C13—C14—H14B	109.5	C29—N3—H3E	107.6
H14A—C14—H14B	109.5	Zn1—N3—H3E	107.6
C13—C14—H14C	109.5	H3D—N3—H3E	107
H14A—C14—H14C	109.5	C1—O1—Si1	131.67 (10)
H14B—C14—H14C	109.5	C5—O2—Si1	130.44 (10)
C13—C15—H15A	109.5	C9—O3—Si1	131.24 (10)
C13—C15—H15B	109.5	C13—O4—Si2	130.32 (10)
H15A—C15—H15B	109.5	C17—O5—Si2	133.16 (10)
C13—C15—H15C	109.5	C21—O6—Si2	132.98 (11)
H15A—C15—H15C	109.5	O3—Si1—O1	105.69 (6)
H15B—C15—H15C	109.5	O3—Si1—O2	103.76 (6)
C13—C16—H16A	109.5	O1—Si1—O2	111.48 (6)
C13—C16—H16B	109.5	O3—Si1—S1	116.42 (5)
H16A—C16—H16B	109.5	O1—Si1—S1	109.95 (4)
C13—C16—H16C	109.5	O2—Si1—S1	109.40 (4)
H16A—C16—H16C	109.5	O5—Si2—O6	111.88 (7)
H16B—C16—H16C	109.5	O5—Si2—O4	106.16 (6)
O5—C17—C20	111.33 (14)	O6—Si2—O4	105.71 (6)
O5—C17—C19	105.23 (14)	O5—Si2—S2	112.71 (5)
C20—C17—C19	110.80 (16)	O6—Si2—S2	106.20 (5)
O5—C17—C18	109.01 (14)	O4—Si2—S2	114.06 (4)
C20—C17—C18	110.48 (15)	Si1—S1—Zn1	110.33 (2)
C19—C17—C18	109.86 (16)	Si2—S2—Zn1	102.24 (2)
C17—C18—H18A	109.5	N1—Zn1—N3	95.74 (5)
C17—C18—H18B	109.5	N1—Zn1—S1	119.20 (4)
H18A—C18—H18B	109.5	N3—Zn1—S1	107.25 (4)
C17—C18—H18C	109.5	N1—Zn1—S2	110.88 (4)
H18A—C18—H18C	109.5	N3—Zn1—S2	116.88 (4)
H18B—C18—H18C	109.5	S1—Zn1—S2	107.053 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2^i	0.88	2.52	3.2481 (14)	140
N2—H2···O6^i	0.88	2.57	3.355 (2)	148
N3—H3D···O4	0.92	2.24	3.0550 (17)	147
N3—H3E···O2	0.92	2.20	3.0592 (17)	156

Symmetry code: (i) −x, −y+1, −z+1.

(V) [2-(1H-imidazol-4-yl-κN³)methanol]bis(tri-tert- butoxysilanethiolato-κ²O,S)zinc(II)

Crystal data

[Zn(C12H27O3SSi)2(C4H6N2O)]	F(000) = 1552
Mr = 722.45	Dx = 1.225 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24929 reflections
a = 16.2546 (5) Å	θ = 2.2–32.4°
b = 9.2094 (2) Å	µ = 0.83 mm^−1
c = 26.1831 (7) Å	T = 120 K
β = 91.874 (2)°	Prism, colourless
V = 3917.39 (18) Å^3	0.39 × 0.2 × 0.04 mm
Z = 4

Data collection

Oxford Diffraction KM-4 CCD diffractometer	7283 independent reflections
Graphite monochromator	6253 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	Rint = 0.043
ω scans, 0.65 deg width	θmax = 25.5°, θmin = 2.3°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid [(1995). Acta Cryst. A51, 887-897]	h = −19→14
Tmin = 0.685, Tmax = 0.855	k = −10→11
25278 measured reflections	l = −31→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 2.7099P] where P = (Fo^2 + 2Fc^2)/3
7283 reflections	(Δ/σ)max = 0.001
429 parameters	Δρmax = 0.99 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.23346 (15)	0.3039 (3)	0.16915 (9)	0.0238 (5)
C2	0.14046 (16)	0.2951 (3)	0.16199 (12)	0.0377 (7)
H2A	0.1259	0.2103	0.141	0.057*
H2B	0.12	0.3834	0.1449	0.057*
H2C	0.1155	0.286	0.1954	0.057*
C3	0.27371 (17)	0.3146 (3)	0.11735 (10)	0.0289 (6)
H3A	0.3337	0.3184	0.1225	0.043*
H3B	0.2546	0.4028	0.0997	0.043*
H3C	0.2587	0.2294	0.0966	0.043*
C4	0.2586 (2)	0.4303 (3)	0.20298 (11)	0.0365 (7)
H4A	0.2331	0.4203	0.2362	0.055*
H4B	0.2405	0.5213	0.1868	0.055*
H4C	0.3187	0.4312	0.2079	0.055*
C5	0.31387 (15)	−0.1437 (3)	0.09502 (9)	0.0247 (5)
C6	0.23949 (17)	−0.2289 (3)	0.07445 (11)	0.0360 (6)
H6A	0.2134	−0.2789	0.1027	0.054*
H6B	0.2573	−0.3004	0.0494	0.054*
H6C	0.1999	−0.162	0.058	0.054*
C7	0.3549 (2)	−0.0601 (4)	0.05273 (11)	0.0408 (7)
H7A	0.3151	0.0071	0.0367	0.061*
H7B	0.3743	−0.1283	0.027	0.061*
H7C	0.4017	−0.0051	0.0672	0.061*
C8	0.37455 (16)	−0.2458 (3)	0.12210 (11)	0.0308 (6)
H8A	0.4223	−0.1903	0.135	0.046*
H8B	0.3926	−0.3198	0.098	0.046*
H8C	0.3478	−0.2929	0.1507	0.046*
C9	0.48478 (14)	0.1475 (3)	0.19331 (10)	0.0232 (5)
C10	0.4992 (2)	0.2909 (4)	0.16792 (14)	0.0540 (10)
H10A	0.5037	0.2763	0.131	0.081*
H10B	0.5504	0.3339	0.1819	0.081*
H10C	0.4531	0.3563	0.1743	0.081*
C11	0.4724 (2)	0.1677 (5)	0.24981 (12)	0.0578 (11)
H11A	0.4232	0.2269	0.2548	0.087*
H11B	0.5206	0.2165	0.2654	0.087*
H11C	0.4654	0.0726	0.2659	0.087*
C12	0.5552 (2)	0.0463 (4)	0.1851 (2)	0.0666 (12)
H12A	0.5444	−0.047	0.2015	0.1*
H12B	0.6059	0.0884	0.2001	0.1*
H12C	0.5616	0.0314	0.1484	0.1*
C13	0.17112 (16)	−0.1797 (3)	0.38238 (9)	0.0237 (5)
C14	0.07796 (17)	−0.1894 (3)	0.37548 (12)	0.0371 (7)
H14A	0.0523	−0.1125	0.3954	0.056*
H14B	0.0592	−0.2843	0.3874	0.056*
H14C	0.0624	−0.1776	0.3392	0.056*
C15	0.2130 (2)	−0.2910 (3)	0.34966 (12)	0.0385 (7)
H15A	0.1959	−0.2767	0.3138	0.058*
H15B	0.1974	−0.3888	0.3605	0.058*
H15C	0.2729	−0.2797	0.3535	0.058*
C16	0.19733 (19)	−0.1970 (3)	0.43842 (10)	0.0344 (6)
H16A	0.257	−0.1841	0.4423	0.052*
H16B	0.1824	−0.2942	0.4501	0.052*
H16C	0.1694	−0.1238	0.4588	0.052*
C17	0.35957 (15)	0.1461 (3)	0.44011 (10)	0.0267 (6)
C18	0.38183 (18)	0.3051 (3)	0.43204 (12)	0.0394 (7)
H18A	0.3644	0.3348	0.3974	0.059*
H18B	0.4415	0.3175	0.4365	0.059*
H18C	0.3539	0.3653	0.457	0.059*
C19	0.39767 (17)	0.0502 (4)	0.40023 (13)	0.0401 (7)
H19A	0.3795	−0.0503	0.4049	0.06*
H19B	0.4578	0.0549	0.404	0.06*
H19C	0.3803	0.0839	0.366	0.06*
C20	0.38595 (18)	0.0986 (4)	0.49390 (12)	0.0451 (8)
H20A	0.3585	0.1594	0.5189	0.068*
H20B	0.4457	0.109	0.4985	0.068*
H20C	0.3706	−0.0032	0.4989	0.068*
C21	0.08733 (16)	0.2399 (3)	0.45826 (10)	0.0276 (6)
C22	0.1249 (9)	0.2071 (16)	0.5090 (5)	0.039 (3)	0.65 (3)
H22A	0.1102	0.1082	0.519	0.058*	0.65 (3)
H22B	0.1047	0.2762	0.5341	0.058*	0.65 (3)
H22C	0.1849	0.2152	0.5076	0.058*	0.65 (3)
C23	0.1017 (9)	0.3944 (8)	0.4405 (4)	0.046 (2)	0.65 (3)
H23A	0.1605	0.4092	0.4353	0.069*	0.65 (3)
H23B	0.083	0.4625	0.4664	0.069*	0.65 (3)
H23C	0.0708	0.4113	0.4083	0.069*	0.65 (3)
C24	−0.0087 (7)	0.2140 (14)	0.4594 (5)	0.035 (2)	0.65 (3)
H24A	−0.0332	0.2299	0.4251	0.052*	0.65 (3)
H24B	−0.0329	0.2819	0.4835	0.052*	0.65 (3)
H24C	−0.0195	0.1141	0.4702	0.052*	0.65 (3)
C22A	0.117 (2)	0.156 (3)	0.5082 (10)	0.043 (5)	0.35 (3)
H22D	0.0976	0.056	0.5068	0.064*	0.35 (3)
H22E	0.0957	0.2048	0.5383	0.064*	0.35 (3)
H22F	0.1778	0.1568	0.5106	0.064*	0.35 (3)
C23A	0.1363 (14)	0.3883 (16)	0.4589 (11)	0.051 (5)	0.35 (3)
H23D	0.1944	0.3698	0.4677	0.076*	0.35 (3)
H23E	0.1133	0.4536	0.4843	0.076*	0.35 (3)
H23F	0.1317	0.4335	0.425	0.076*	0.35 (3)
C24A	0.0038 (14)	0.260 (3)	0.4559 (9)	0.042 (5)	0.35 (3)
H24D	−0.0107	0.3273	0.428	0.063*	0.35 (3)
H24E	−0.0141	0.3007	0.4883	0.063*	0.35 (3)
H24F	−0.0236	0.1667	0.4496	0.063*	0.35 (3)
C25	0.03948 (14)	0.0966 (3)	0.28075 (9)	0.0219 (5)
H25	0.0489	0.1558	0.3101	0.026*
C26	−0.02386 (15)	−0.0196 (3)	0.21849 (10)	0.0242 (5)
H26	−0.0658	−0.0569	0.196	0.029*
C27	0.05823 (14)	−0.0441 (3)	0.21601 (9)	0.0201 (5)
C28	0.10370 (14)	−0.1292 (3)	0.17747 (9)	0.0226 (5)
H28A	0.0638	−0.1661	0.1512	0.029*
H28B	0.1423	−0.0635	0.1602	0.029*
N1	0.09808 (12)	0.0310 (2)	0.25592 (7)	0.0194 (4)
N2	−0.03456 (12)	0.0697 (2)	0.25973 (8)	0.0239 (5)
H2	−0.0818	0.1031	0.2703	0.029*
O1	0.25909 (10)	0.17131 (17)	0.19624 (6)	0.0197 (3)
O2	0.28119 (10)	−0.03839 (18)	0.13005 (6)	0.0206 (4)
O3	0.41294 (10)	0.08376 (18)	0.16767 (6)	0.0216 (4)
O4	0.19715 (10)	−0.03761 (17)	0.36335 (6)	0.0213 (4)
O5	0.27078 (10)	0.13174 (19)	0.43794 (6)	0.0219 (4)
O6	0.11396 (10)	0.14540 (19)	0.41829 (6)	0.0242 (4)
O7	0.14903 (10)	−0.24901 (18)	0.19865 (7)	0.0242 (4)
H7	0.1954	−0.2202	0.2096	0.029*
Si1	0.32091 (4)	0.03626 (7)	0.18176 (2)	0.01611 (14)
Si2	0.20247 (4)	0.12294 (7)	0.39136 (2)	0.01828 (15)
S1	0.31089 (3)	−0.09740 (6)	0.24631 (2)	0.01777 (13)
S2	0.22374 (4)	0.26116 (6)	0.33014 (2)	0.02213 (15)
Zn1	0.218216 (16)	0.06420 (3)	0.277116 (10)	0.02073 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0302 (13)	0.0195 (12)	0.0217 (12)	0.0051 (10)	0.0024 (10)	0.0067 (10)
C2	0.0298 (14)	0.0428 (17)	0.0406 (16)	0.0090 (12)	0.0041 (12)	0.0212 (14)
C3	0.0355 (14)	0.0279 (14)	0.0234 (13)	0.0050 (11)	0.0043 (11)	0.0086 (11)
C4	0.0607 (19)	0.0231 (14)	0.0260 (14)	0.0051 (13)	0.0053 (13)	0.0044 (11)
C5	0.0296 (13)	0.0264 (13)	0.0185 (12)	−0.0014 (10)	0.0076 (10)	−0.0050 (10)
C6	0.0363 (15)	0.0451 (17)	0.0266 (14)	−0.0032 (13)	0.0000 (11)	−0.0148 (13)
C7	0.0514 (18)	0.0476 (18)	0.0244 (14)	−0.0036 (14)	0.0171 (13)	0.0003 (13)
C8	0.0320 (14)	0.0288 (14)	0.0317 (14)	0.0037 (11)	0.0031 (11)	−0.0108 (12)
C9	0.0198 (11)	0.0235 (12)	0.0261 (13)	−0.0057 (9)	0.0004 (10)	0.0019 (10)
C10	0.054 (2)	0.0476 (19)	0.058 (2)	−0.0290 (16)	−0.0263 (17)	0.0217 (17)
C11	0.0433 (18)	0.100 (3)	0.0301 (16)	−0.0392 (19)	−0.0011 (14)	−0.0116 (18)
C12	0.0311 (17)	0.053 (2)	0.114 (4)	0.0096 (15)	−0.017 (2)	−0.030 (2)
C13	0.0342 (13)	0.0164 (12)	0.0207 (12)	−0.0049 (10)	0.0025 (10)	0.0038 (10)
C14	0.0354 (15)	0.0287 (15)	0.0469 (18)	−0.0103 (12)	−0.0015 (13)	0.0077 (13)
C15	0.0612 (19)	0.0202 (13)	0.0351 (16)	−0.0031 (13)	0.0160 (14)	0.0018 (12)
C16	0.0510 (17)	0.0275 (14)	0.0244 (14)	−0.0057 (12)	−0.0014 (12)	0.0068 (11)
C17	0.0204 (12)	0.0384 (15)	0.0214 (12)	−0.0001 (10)	0.0016 (10)	−0.0072 (11)
C18	0.0353 (15)	0.0450 (18)	0.0380 (16)	−0.0132 (13)	0.0027 (12)	−0.0104 (14)
C19	0.0266 (14)	0.0499 (19)	0.0442 (17)	0.0008 (12)	0.0086 (12)	−0.0182 (15)
C20	0.0277 (15)	0.072 (2)	0.0355 (17)	0.0053 (15)	−0.0052 (12)	0.0035 (16)
C21	0.0315 (14)	0.0307 (14)	0.0213 (12)	0.0022 (11)	0.0099 (10)	−0.0030 (11)
C22	0.036 (3)	0.058 (7)	0.021 (3)	0.014 (5)	−0.002 (2)	−0.010 (5)
C23	0.050 (6)	0.032 (3)	0.058 (5)	0.000 (3)	0.029 (4)	−0.009 (3)
C24	0.016 (3)	0.056 (6)	0.032 (3)	0.003 (3)	0.010 (2)	0.015 (4)
C22A	0.063 (11)	0.050 (12)	0.016 (6)	0.017 (9)	0.013 (6)	−0.009 (8)
C23A	0.048 (9)	0.022 (5)	0.083 (13)	−0.002 (6)	0.025 (8)	−0.019 (7)
C24A	0.040 (8)	0.065 (13)	0.023 (6)	−0.014 (8)	0.015 (5)	−0.007 (7)
C25	0.0230 (12)	0.0205 (12)	0.0225 (12)	0.0017 (9)	0.0050 (10)	0.0001 (10)
C26	0.0224 (12)	0.0214 (12)	0.0287 (13)	−0.0008 (10)	−0.0010 (10)	−0.0013 (10)
C27	0.0212 (11)	0.0189 (11)	0.0201 (12)	−0.0018 (9)	0.0003 (9)	0.0034 (9)
C28	0.0207 (11)	0.0270 (13)	0.0200 (12)	−0.0024 (10)	0.0002 (9)	−0.0019 (10)
N1	0.0192 (10)	0.0205 (10)	0.0184 (10)	0.0006 (8)	0.0027 (8)	−0.0003 (8)
N2	0.0182 (10)	0.0228 (11)	0.0310 (12)	0.0025 (8)	0.0046 (8)	0.0001 (9)
O1	0.0257 (8)	0.0184 (8)	0.0151 (8)	0.0032 (7)	0.0027 (6)	0.0039 (7)
O2	0.0227 (8)	0.0234 (9)	0.0159 (8)	−0.0008 (7)	0.0008 (6)	−0.0020 (7)
O3	0.0217 (8)	0.0236 (9)	0.0198 (8)	−0.0054 (7)	0.0035 (7)	−0.0015 (7)
O4	0.0302 (9)	0.0168 (8)	0.0170 (8)	−0.0040 (7)	0.0027 (7)	0.0019 (7)
O5	0.0210 (8)	0.0286 (9)	0.0160 (8)	−0.0004 (7)	0.0020 (6)	−0.0018 (7)
O6	0.0244 (9)	0.0299 (9)	0.0186 (8)	−0.0004 (7)	0.0043 (7)	−0.0031 (7)
O7	0.0193 (8)	0.0206 (9)	0.0329 (10)	−0.0024 (7)	0.0038 (7)	−0.0041 (7)
Si1	0.0175 (3)	0.0168 (3)	0.0141 (3)	−0.0008 (2)	0.0017 (2)	0.0003 (2)
Si2	0.0229 (3)	0.0184 (3)	0.0137 (3)	−0.0013 (2)	0.0024 (2)	−0.0005 (2)
S1	0.0188 (3)	0.0174 (3)	0.0172 (3)	0.0016 (2)	0.0025 (2)	0.0029 (2)
S2	0.0337 (3)	0.0170 (3)	0.0159 (3)	−0.0026 (2)	0.0036 (2)	−0.0002 (2)
Zn1	0.01924 (16)	0.02318 (17)	0.01979 (16)	0.00064 (10)	0.00101 (11)	−0.00635 (11)

Geometric parameters (Å, º)

C1—O1	1.466 (3)	C18—H18C	0.98
C1—C4	1.511 (4)	C19—H19A	0.98
C1—C2	1.519 (4)	C19—H19B	0.98
C1—C3	1.528 (3)	C19—H19C	0.98
C2—H2A	0.98	C20—H20A	0.98
C2—H2B	0.98	C20—H20B	0.98
C2—H2C	0.98	C20—H20C	0.98
C3—H3A	0.98	C21—C24A	1.37 (2)
C3—H3B	0.98	C21—O6	1.439 (3)
C3—H3C	0.98	C21—C22	1.476 (14)
C4—H4A	0.98	C21—C23	1.517 (8)
C4—H4B	0.98	C21—C24	1.580 (11)
C4—H4C	0.98	C21—C23A	1.582 (15)
C5—O2	1.448 (3)	C21—C22A	1.58 (3)
C5—C7	1.521 (4)	C22—H22A	0.98
C5—C8	1.521 (4)	C22—H22B	0.98
C5—C6	1.524 (4)	C22—H22C	0.98
C6—H6A	0.98	C23—H23A	0.98
C6—H6B	0.98	C23—H23B	0.98
C6—H6C	0.98	C23—H23C	0.98
C7—H7A	0.98	C24—H24A	0.98
C7—H7B	0.98	C24—H24B	0.98
C7—H7C	0.98	C24—H24C	0.98
C8—H8A	0.98	C22A—H22D	0.98
C8—H8B	0.98	C22A—H22E	0.98
C8—H8C	0.98	C22A—H22F	0.98
C9—O3	1.452 (3)	C23A—H23D	0.98
C9—C12	1.497 (4)	C23A—H23E	0.98
C9—C10	1.501 (4)	C23A—H23F	0.98
C9—C11	1.511 (4)	C24A—H24D	0.98
C10—H10A	0.98	C24A—H24E	0.98
C10—H10B	0.98	C24A—H24F	0.98
C10—H10C	0.98	C25—N1	1.317 (3)
C11—H11A	0.98	C25—N2	1.330 (3)
C11—H11B	0.98	C25—H25	0.95
C11—H11C	0.98	C26—C27	1.357 (3)
C12—H12A	0.98	C26—N2	1.373 (3)
C12—H12B	0.98	C26—H26	0.95
C12—H12C	0.98	C27—N1	1.395 (3)
C13—O4	1.467 (3)	C27—C28	1.492 (3)
C13—C15	1.512 (4)	C28—O7	1.429 (3)
C13—C14	1.522 (4)	C28—H28A	0.99
C13—C16	1.523 (3)	C28—H28B	0.99
C14—H14A	0.98	N1—Zn1	2.0357 (19)
C14—H14B	0.98	N2—H2	0.88
C14—H14C	0.98	O1—Si1	1.6507 (17)
C15—H15A	0.98	O1—Zn1	2.4477 (15)
C15—H15B	0.98	O2—Si1	1.6326 (17)
C15—H15C	0.98	O3—Si1	1.6129 (16)
C16—H16A	0.98	O4—Si2	1.6514 (17)
C16—H16B	0.98	O4—Zn1	2.4789 (16)
C16—H16C	0.98	O5—Si2	1.6242 (17)
C17—O5	1.449 (3)	O6—Si2	1.6358 (17)
C17—C19	1.515 (4)	O7—H7	0.84
C17—C20	1.523 (4)	Si1—S1	2.1016 (8)
C17—C18	1.525 (4)	Si2—S2	2.0846 (9)
C18—H18A	0.98	S1—Zn1	2.2835 (6)
C18—H18B	0.98	S2—Zn1	2.2841 (6)
O1—C1—C4	106.90 (19)	C17—C19—H19C	109.5
O1—C1—C2	106.32 (19)	H19A—C19—H19C	109.5
C4—C1—C2	111.3 (2)	H19B—C19—H19C	109.5
O1—C1—C3	111.09 (19)	C17—C20—H20A	109.5
C4—C1—C3	110.8 (2)	C17—C20—H20B	109.5
C2—C1—C3	110.3 (2)	H20A—C20—H20B	109.5
C1—C2—H2A	109.5	C17—C20—H20C	109.5
C1—C2—H2B	109.5	H20A—C20—H20C	109.5
H2A—C2—H2B	109.5	H20B—C20—H20C	109.5
C1—C2—H2C	109.5	C24A—C21—O6	111.7 (10)
H2A—C2—H2C	109.5	C24A—C21—C22	116.7 (11)
H2B—C2—H2C	109.5	O6—C21—C22	113.9 (6)
C1—C3—H3A	109.5	C24A—C21—C23	91.2 (9)
C1—C3—H3B	109.5	O6—C21—C23	106.9 (3)
H3A—C3—H3B	109.5	C22—C21—C23	113.9 (5)
C1—C3—H3C	109.5	O6—C21—C24	104.0 (5)
H3A—C3—H3C	109.5	C22—C21—C24	109.5 (7)
H3B—C3—H3C	109.5	C23—C21—C24	108.0 (5)
C1—C4—H4A	109.5	C24A—C21—C23A	112.4 (10)
C1—C4—H4B	109.5	O6—C21—C23A	111.5 (6)
H4A—C4—H4B	109.5	C22—C21—C23A	88.5 (10)
C1—C4—H4C	109.5	C24—C21—C23A	128.9 (7)
H4A—C4—H4C	109.5	C24A—C21—C22A	112.5 (14)
H4B—C4—H4C	109.5	O6—C21—C22A	102.4 (9)
O2—C5—C7	107.5 (2)	C23—C21—C22A	131.5 (9)
O2—C5—C8	111.4 (2)	C24—C21—C22A	101.0 (12)
C7—C5—C8	111.1 (2)	C23A—C21—C22A	105.6 (11)
O2—C5—C6	105.39 (19)	C21—C22—H22A	109.5
C7—C5—C6	111.4 (2)	C21—C22—H22B	109.5
C8—C5—C6	110.0 (2)	C21—C22—H22C	109.5
C5—C6—H6A	109.5	C21—C23—H23A	109.5
C5—C6—H6B	109.5	C21—C23—H23B	109.5
H6A—C6—H6B	109.5	C21—C23—H23C	109.5
C5—C6—H6C	109.5	C21—C24—H24A	109.5
H6A—C6—H6C	109.5	C21—C24—H24B	109.5
H6B—C6—H6C	109.5	C21—C24—H24C	109.5
C5—C7—H7A	109.5	C21—C22A—H22D	109.5
C5—C7—H7B	109.5	C21—C22A—H22E	109.5
H7A—C7—H7B	109.5	H22D—C22A—H22E	109.5
C5—C7—H7C	109.5	C21—C22A—H22F	109.5
H7A—C7—H7C	109.5	H22D—C22A—H22F	109.5
H7B—C7—H7C	109.5	H22E—C22A—H22F	109.5
C5—C8—H8A	109.5	C21—C23A—H23D	109.5
C5—C8—H8B	109.5	C21—C23A—H23E	109.5
H8A—C8—H8B	109.5	H23D—C23A—H23E	109.5
C5—C8—H8C	109.5	C21—C23A—H23F	109.5
H8A—C8—H8C	109.5	H23D—C23A—H23F	109.5
H8B—C8—H8C	109.5	H23E—C23A—H23F	109.5
O3—C9—C12	106.8 (2)	C21—C24A—H24D	109.5
O3—C9—C10	106.6 (2)	C21—C24A—H24E	109.5
C12—C9—C10	110.6 (3)	H24D—C24A—H24E	109.5
O3—C9—C11	111.8 (2)	C21—C24A—H24F	109.5
C12—C9—C11	110.1 (3)	H24D—C24A—H24F	109.5
C10—C9—C11	110.7 (3)	H24E—C24A—H24F	109.5
C9—C10—H10A	109.5	N1—C25—N2	111.7 (2)
C9—C10—H10B	109.5	N1—C25—H25	124.2
H10A—C10—H10B	109.5	N2—C25—H25	124.2
C9—C10—H10C	109.5	C27—C26—N2	106.7 (2)
H10A—C10—H10C	109.5	C27—C26—H26	126.6
H10B—C10—H10C	109.5	N2—C26—H26	126.6
C9—C11—H11A	109.5	C26—C27—N1	108.4 (2)
C9—C11—H11B	109.5	C26—C27—C28	129.0 (2)
H11A—C11—H11B	109.5	N1—C27—C28	122.6 (2)
C9—C11—H11C	109.5	O7—C28—C27	113.79 (19)
H11A—C11—H11C	109.5	O7—C28—H28A	108.8
H11B—C11—H11C	109.5	C27—C28—H28A	108.8
C9—C12—H12A	109.5	O7—C28—H28B	108.8
C9—C12—H12B	109.5	C27—C28—H28B	108.8
H12A—C12—H12B	109.5	H28A—C28—H28B	107.7
C9—C12—H12C	109.5	C25—N1—C27	105.8 (2)
H12A—C12—H12C	109.5	C25—N1—Zn1	119.94 (17)
H12B—C12—H12C	109.5	C27—N1—Zn1	134.16 (16)
O4—C13—C15	105.78 (19)	C25—N2—C26	107.5 (2)
O4—C13—C14	108.0 (2)	C25—N2—H2	126.3
C15—C13—C14	111.0 (2)	C26—N2—H2	126.3
O4—C13—C16	110.2 (2)	C1—O1—Si1	133.01 (14)
C15—C13—C16	111.0 (2)	C1—O1—Zn1	132.33 (13)
C14—C13—C16	110.7 (2)	Si1—O1—Zn1	94.56 (7)
C13—C14—H14A	109.5	C5—O2—Si1	131.63 (15)
C13—C14—H14B	109.5	C9—O3—Si1	137.89 (15)
H14A—C14—H14B	109.5	C13—O4—Si2	131.22 (15)
C13—C14—H14C	109.5	C13—O4—Zn1	134.15 (14)
H14A—C14—H14C	109.5	Si2—O4—Zn1	93.38 (7)
H14B—C14—H14C	109.5	C17—O5—Si2	133.62 (15)
C13—C15—H15A	109.5	C21—O6—Si2	132.83 (16)
C13—C15—H15B	109.5	C28—O7—H7	109.5
H15A—C15—H15B	109.5	O3—Si1—O2	105.61 (9)
C13—C15—H15C	109.5	O3—Si1—O1	115.10 (9)
H15A—C15—H15C	109.5	O2—Si1—O1	106.30 (9)
H15B—C15—H15C	109.5	O3—Si1—S1	116.08 (7)
C13—C16—H16A	109.5	O2—Si1—S1	112.42 (7)
C13—C16—H16B	109.5	O1—Si1—S1	101.12 (6)
H16A—C16—H16B	109.5	O5—Si2—O6	105.03 (9)
C13—C16—H16C	109.5	O5—Si2—O4	113.75 (9)
H16A—C16—H16C	109.5	O6—Si2—O4	105.70 (9)
H16B—C16—H16C	109.5	O5—Si2—S2	114.86 (7)
O5—C17—C19	110.4 (2)	O6—Si2—S2	115.12 (7)
O5—C17—C20	105.1 (2)	O4—Si2—S2	102.29 (6)
C19—C17—C20	111.1 (3)	Si1—S1—Zn1	88.38 (3)
O5—C17—C18	108.8 (2)	Si2—S2—Zn1	88.75 (3)
C19—C17—C18	111.1 (2)	N1—Zn1—S1	116.34 (6)
C20—C17—C18	110.1 (2)	N1—Zn1—S2	107.66 (6)
C17—C18—H18A	109.5	S1—Zn1—S2	135.97 (2)
C17—C18—H18B	109.5	N1—Zn1—O1	96.30 (7)
H18A—C18—H18B	109.5	S1—Zn1—O1	75.89 (4)
C17—C18—H18C	109.5	S2—Zn1—O1	101.51 (4)
H18A—C18—H18C	109.5	N1—Zn1—O4	91.81 (7)
H18B—C18—H18C	109.5	S1—Zn1—O4	100.81 (4)
C17—C19—H19A	109.5	S2—Zn1—O4	75.56 (4)
C17—C19—H19B	109.5	O1—Zn1—O4	171.88 (5)
H19A—C19—H19B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7^i	0.88	1.94	2.751 (3)	152
O7—H7···S1	0.84	2.37	3.1959 (17)	168

Symmetry code: (i) −x, y+1/2, −z+1/2.