Bis[1-(2-hydroxy­ethyl)-4,10-diaza­pyrazolo[4,3-b]fluoren-5(1H)-one thio­semicarbazonato]zinc(II) dimethyl­formamide tris­olvate monohydrate

In the title Schiff base complex, [Zn(C₁₅H₁₂N₇OS)₂]·3C₃H₇NO·H₂O, each Zn^II atom is six-coordinated in a distorted octa­hedral environment by two ligands acting in a tridentate chelating mode through two N atoms and one S atom. The coordination mode of the ligand is nearly planar. There are three dimethyl­formamide mol­ecules and one water mol­ecule solvating the complex. The coordination behavior of the ligand is compared with that of related ligands in similar complexes.

S1. Comment

Owing to their photoelectromagnetic characteristics and physiologically important bactericidal and cancer-fighting activities, the hydrazone class of Schiff bases and their complexes have attracted much attention (Reiter et al., 1985; Kovala-Demertzi et al., 1999; Matthews et al., 2001). Among these, the thiosemicarbazide Schiff base and its complexes have been particularly widely studied, because they are not only organic colorants with excellent performance, showing antibacterial and antiviral activities, but also templates for studying biological activity (Singh et al., 1978). The title compound, [ZnL₂]·3DMF·H₂O, (I) {L is 3-(2-hydroxyethyl)-4,10-diazapyrazolo[3,4-b]fluoren-9(3H)-one thiosemicarbazone and DMF is dimethylformamide}, has been synthesized because the ligand L is not only a novel thiosemicarbazone Schiff base but also a member of an important class of pyrazole-containing ring structures. This type of ligand displays unusual characteristics, including cis–trans isomerism in complexes (Che & Wang, 2006; Che et al., 2006). Therefore, we aim to determine the single-crystal structures of examples of this class of compound, in order to understand their coordination mode and structural characteristics, as a guide for further studies. To our knowledge, this is the first report of the synthesis and crystal structure of a complex of this ligand.

The title complex, (I), in which the molecular structure unit is identical to the asymmetric unit, is composed of one ZnL₂ unit, one water molecule and three DMF molecules, with the solvent molecules not participating in coordination. Within the complex, each Zn^II ion is six-coordinated (Fig. 1) by four N and two S atoms from two ligands. The bond angles formed between atom Zn1 and coordination atoms N2, N4, S1, N9, N11 and S2 are in the range of 62.63 (8)–110.76 (9)°, while the bond lengths involving atom Zn1 and these coordination atoms are in the range 1.978 (3)–2.739 (1) Å. Thus, the central Zn coordination geometry is best described as a distorted octahedron (Table 1). Each ligand L, as a tridentate chelate, provides two N atoms and one S atom to coordinate to Zn^II, forming a six-membered ring and a four-membered ring. As demonstrated by the relevant literature (Mathew & Palenik, 1971; Restivo & Palenik, 1970; Gabe et al., 1969), this type of thiosemicarbazide Schiff base has a large conformational diversity, so that cis–trans isomerism is observed. The coordination mode of the present ligand L is very different from that of these reported examples. Using one of the independent L ligands as an example, atom N2 is in the cis (not trans) position with respect to N4 on the diazafluorenone ring, and it is N2 (not N3) that coordinates to the Zn^II atom. The cause may that the present Schiff base ligand L is synthesized directly from the carbonyl group in the aromatic ring, while most Schiff base ligands are synthesized from aldehyde groups and those carbonyl groups that are not in the aromatic ring (Mathew & Palenik, 1971; Restivo & Palenik, 1970; Gabe et al., 1969). There may exist cis–trans isomerism for this ligand as well, because this coordination mode is similar to that observed in bis(µ-11-thiosemicarbazonoindeno[1,2-b]quinoxaline-8-carboxyl- ato)bis[(dimethyl sulfoxide)zinc(II)] dimethyl sulfoxide trisolvate, (IIa) (Che et al., 2006), but different from that found in the indene[1,2-b]quinoxalin-11-alkone thiosemicarbazone–cobalt(II) Schiff base complex (Che & Wang, 2006), (IIb), in which N3 (not N2) coordinates to the metal atom. Although many examples of cis–trans isomerism in Schiff base ligands have been observed, the existence of complexes with both isomers of a given ligand are rarely reported. The reason for the cis–trans conversion is still unknown.

The C17—N10 bond length in (I) [1.324 (4) Å] indicates a double bond and the compound exists in the imide form. The C16—S1 bond length [1.667 (4) Å] is intermediate between 1.82 Å for a C—S single bond and 1.56 Å for a C═ S double bond. The C16—N8, C16—N9 and N9—N10 bonds [1.336 (5), 1.360 (4) and 1.348 (4) Å] are indicative of some double-bond character. Except for the hydroxyethyl group, all other non-H atoms (C1–C13, N1–N7 and S1) within L are in the same plane (the mean deviation of the atoms from the least-squares plane is 0.0180 Å), with the Zn^II ion located in the center, 0.181 (1) Å from the plane. The dihedral angle between the least-squares planes of the two ligands is 87.4 (2)°. Atom N5 at another potential coordinating position of the diazafluorenone ring does not participate in coordination, and so only a simple coordination compound forms rather than a coordination polymer. This is presumably due to steric hindrance. Thus, the complex is a simple structure rather than a dimeric structure and the metal center is six-coordinate rather than five-coordinate, which is diffrent from what was previously observed in bis(µ-11-thiosemicarbazonoindeno[1,2-b]quinoxaline-8-carboxyl- ato)bis[(dimethyl sulfoxide)zinc(II)] dimethyl sulfoxide trisolvate (Che et al., 2006).

The packing diagram of (I) (Fig. 2) shows that the intermolecular interactions are mainly mediated by hydrogen bonds between NH donors and N, O and S acceptors (Table 2), which lead to the formation of a three-dimensional supermolecular structure. There are also some hydrogen-bonding interactions between the disordered DMF molecules and the hydroxyethyl group, but these are difficult to evaluate with precision because of the disorder.

Related literature

For related literature, see: Che & Wang (2006b); Che et al. (2006a); Gabe et al. (1969); Kovala-Demertzi, Miller, Kourkoumelis, Hadjikakou & Demertzis (1999); Mathew & Palenik (1971); Matthews et al. (2001); Reiter et al. (1985); Restivo & Palenik (1970); Singh et al. (1978).

S2. Experimental

All reagents were purchased from Aldrich and used without further purification. The ligand L was synthesized according to a reported method (Che et al., 2006). Ligand L (0.760 g, 0.002 mol) was dissolved in DMF (20 ml) and then Zn(OAc)₂·6H₂O (0.237 g, 0.001 mol) was added. After heating at 373 K for 20 min, the mixture was allowed to cool and evaporate naturally. After a few days, red crystalline lumps formed (yield 0.51 g, ca 56.6% based on Zn). Analysis found: C 47.30, H 4.71, N 24.12, S 6.71%; C₃₉H₄₇N₁₇O₆S₂Zn requires: C 47.83, H 4.84, N 24.31, S 6.55%.

S3. Refinement

H atoms were generated geometrically and refined as riding atoms with C—H = 0.93 Å (CH), 0.96 Å (CH₃) and 0.97 Å (CH₂), N—H = 0.86 Å (NH₂), U_iso(H)= 1.2*U_eq(C) or U_eq(N) for CH and NH₂, U_iso(H)= 1.5*U_eq(C) for CH₃ and CH₂. One of three DMF solvent molecules is disordered over a major and minor orientation with refined occupancies 0.79 and 0.21. The O2 and C30 atoms in the hydroxyethyl group on one ligand are disordered with refined occupancies of 0.51 and 0.49. Standard DFIX and SIMU restraints were used for the dimensions of the disordered DMF and the hydroxyethyl group. The H atoms attached to the ligand hydroxyl groups and the water molecule were not located. All non-H atoms were refined anisotropically. The highest peak 0.652 e·A^-3 in the final difference map is located 0.98 Å from N3.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001) and local programs.

Figures

	Fig. 1. A view of complex (I), with the atomic labeling scheme. Displacement ellipsoids are shown at the 30% probability level. Solvent DMF molecules and water molecule have been omitted for clarity.
	Fig. 2. A view of the packing of complex (I) along the b axis. Hydrogen bonds are shown as dashed lines. Some solvent DMF molecules have been omitted for clarity.

Bis[3-(2-hydroxyethyl)-4,10-diazapyrazolo[3,4-b]fluoren-9(3H)-one thiosemicarbazonato]zinc(II) dimethylformamide trisolvate monohydrate

Crystal data

[Zn(C15H12N7OS)2]·3C3H7NO·H2O	F(000) = 2032
Mr = 979.43	Dx = 1.378 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 16.530 (5) Å	Cell parameters from 1864 reflections
b = 12.104 (5) Å	θ = 3.7–22.8°
c = 23.601 (5) Å	µ = 0.67 mm^−1
β = 95.191 (5)°	T = 293 K
V = 4703 (3) Å^3	Block, red
Z = 4	0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer	11219 independent reflections
Radiation source: fine-focus sealed tube	5488 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
phi and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→22
Tmin = 0.834, Tmax = 0.877	k = −14→15
28631 measured reflections	l = −27→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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0681P)^2 + 0.5414P] where P = (Fo^2 + 2Fc^2)/3
11219 reflections	(Δ/σ)max = 0.003
659 parameters	Δρmax = 0.65 e Å^−3
221 restraints	Δρmin = −0.46 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)
Zn1	0.28853 (2)	0.29336 (3)	0.566007 (18)	0.05546 (15)
S1	0.43175 (6)	0.40097 (8)	0.55393 (5)	0.0666 (3)
S2	0.26569 (7)	0.36666 (10)	0.66953 (4)	0.0799 (3)
O1	0.2400 (2)	−0.1279 (3)	0.32034 (14)	0.1113 (11)
O2	−0.0955 (5)	0.0229 (7)	0.4924 (4)	0.113 (3)	0.515 (11)
O2'	−0.0603 (6)	−0.0882 (8)	0.5548 (4)	0.125 (4)	0.485 (11)
N1	0.3310 (2)	0.2085 (3)	0.73387 (19)	0.0922 (12)
H1A	0.3556	0.1460	0.7380	0.111*
H1B	0.3198	0.2454	0.7633	0.111*
N2	0.32707 (19)	0.1911 (3)	0.62803 (16)	0.0839 (11)
N3	0.3628 (2)	0.1043 (3)	0.64264 (18)	0.0923 (13)
N4	0.32163 (17)	0.1572 (2)	0.50524 (14)	0.0596 (8)
N5	0.38312 (17)	−0.0289 (2)	0.44344 (13)	0.0548 (7)
N6	0.2904 (2)	0.1763 (3)	0.35280 (16)	0.0817 (10)
N7	0.3281 (2)	0.0760 (3)	0.36269 (14)	0.0690 (9)
N8	0.37734 (18)	0.5373 (3)	0.47002 (14)	0.0752 (9)
H8B	0.3383	0.5638	0.4475	0.090*
H8A	0.4260	0.5616	0.4686	0.090*
N9	0.28585 (17)	0.4190 (2)	0.51005 (13)	0.0574 (7)
N10	0.23015 (18)	0.4653 (2)	0.47206 (13)	0.0590 (8)
N11	0.15973 (16)	0.2753 (2)	0.54575 (12)	0.0524 (7)
N12	−0.01435 (18)	0.2659 (3)	0.51332 (14)	0.0671 (9)
N13	−0.00747 (19)	0.1312 (3)	0.58857 (15)	0.0716 (9)
N14	0.0505 (2)	0.0836 (3)	0.62609 (15)	0.0820 (10)
C1	0.3106 (3)	0.2480 (4)	0.68229 (19)	0.0806 (14)
C2	0.3781 (2)	0.0495 (3)	0.59043 (16)	0.0665 (11)
C3	0.4203 (2)	−0.0558 (3)	0.59608 (17)	0.0618 (10)
C4	0.4518 (3)	−0.1155 (4)	0.64344 (18)	0.0816 (13)
H4	0.4477	−0.0886	0.6800	0.098*
C5	0.4890 (3)	−0.2149 (4)	0.6352 (2)	0.0904 (14)
H5	0.5097	−0.2561	0.6664	0.108*
C6	0.4959 (3)	−0.2538 (4)	0.5814 (2)	0.0807 (12)
H6	0.5217	−0.3212	0.5769	0.097*
C7	0.4660 (2)	−0.1964 (3)	0.53383 (18)	0.0650 (10)
H7	0.4713	−0.2239	0.4976	0.078*
C8	0.4278 (2)	−0.0967 (3)	0.54132 (15)	0.0533 (9)
C9	0.3902 (2)	−0.0192 (3)	0.49981 (16)	0.0534 (9)
C10	0.3595 (2)	0.0715 (3)	0.53061 (17)	0.0576 (9)
C11	0.3449 (2)	0.0590 (3)	0.41903 (16)	0.0572 (9)
C12	0.3149 (2)	0.1508 (3)	0.44815 (19)	0.0607 (10)
C13	0.2821 (3)	0.2197 (3)	0.4029 (2)	0.0797 (12)
H13	0.2577	0.2877	0.4082	0.096*
C14	0.3460 (3)	0.0062 (3)	0.31593 (17)	0.0779 (12)
H14A	0.3842	−0.0505	0.3300	0.094*
H14B	0.3718	0.0502	0.2883	0.094*
C15	0.2711 (3)	−0.0486 (4)	0.28677 (19)	0.0957 (15)
H15A	0.2299	0.0072	0.2773	0.115*
H15B	0.2847	−0.0823	0.2516	0.115*
C16	0.3625 (2)	0.4583 (3)	0.50724 (17)	0.0595 (9)
C17	0.1557 (2)	0.4250 (3)	0.47190 (15)	0.0544 (9)
C18	0.0877 (2)	0.4686 (3)	0.43320 (16)	0.0584 (9)
C19	0.0871 (3)	0.5500 (3)	0.39254 (17)	0.0722 (11)
H19	0.1343	0.5873	0.3854	0.087*
C20	0.0134 (3)	0.5739 (4)	0.36274 (19)	0.0855 (13)
H20	0.0113	0.6280	0.3346	0.103*
C21	−0.0569 (3)	0.5204 (4)	0.3733 (2)	0.0895 (14)
H21	−0.1055	0.5397	0.3528	0.107*
C22	−0.0564 (2)	0.4386 (4)	0.41381 (19)	0.0792 (12)
H22	−0.1041	0.4022	0.4207	0.095*
C23	0.0163 (2)	0.4115 (3)	0.44403 (16)	0.0623 (10)
C24	0.0358 (2)	0.3332 (3)	0.48975 (16)	0.0586 (9)
C25	0.1225 (2)	0.3394 (3)	0.50576 (15)	0.0530 (8)
C26	0.0250 (2)	0.2053 (3)	0.55472 (17)	0.0615 (9)
C27	0.1092 (2)	0.2077 (3)	0.57149 (16)	0.0582 (9)
C28	0.1202 (2)	0.1308 (3)	0.61558 (18)	0.0714 (11)
H28	0.1701	0.1146	0.6352	0.086*
C29	−0.0922 (2)	0.0924 (4)	0.5863 (2)	0.0893 (14)
H29A	−0.1280	0.1528	0.5738	0.107*
H29B	−0.1043	0.0720	0.6244	0.107*
C30	−0.1098 (17)	−0.0045 (16)	0.5475 (8)	0.142 (10)	0.515 (11)
H30A	−0.0755	−0.0662	0.5604	0.170*	0.515 (11)
H30B	−0.1660	−0.0267	0.5485	0.170*	0.515 (11)
C30'	−0.1041 (10)	0.0017 (13)	0.5431 (7)	0.079 (6)	0.485 (11)
H30C	−0.1611	−0.0188	0.5394	0.095*	0.485 (11)
H30D	−0.0911	0.0303	0.5067	0.095*	0.485 (11)
O6W	0.2810 (2)	0.7268 (3)	0.41141 (16)	0.1246 (13)
O3	0.2369 (11)	0.821 (2)	0.5176 (7)	0.186 (6)	0.789 (17)
O3'	0.2336 (19)	0.826 (2)	0.5140 (10)	0.067 (8)	0.211 (17)
N15	0.2491 (11)	0.7490 (12)	0.6025 (7)	0.097 (4)	0.789 (17)
N15'	0.241 (4)	0.752 (4)	0.604 (2)	0.082 (10)	0.211 (17)
C31	0.2586 (5)	0.7465 (8)	0.5494 (4)	0.096 (3)	0.789 (17)
H31	0.2833	0.6850	0.5347	0.115*	0.789 (17)
C31'	0.219 (2)	0.872 (5)	0.564 (3)	0.166 (16)	0.211 (17)
H31'	0.2024	0.9428	0.5739	0.200*	0.211 (17)
C32	0.2079 (8)	0.8406 (11)	0.6274 (6)	0.155 (4)	0.789 (17)
H32A	0.1620	0.8133	0.6452	0.232*	0.789 (17)
H32B	0.1899	0.8924	0.5981	0.232*	0.789 (17)
H32C	0.2447	0.8766	0.6553	0.232*	0.789 (17)
C32'	0.285 (2)	0.653 (3)	0.603 (2)	0.119 (12)	0.211 (17)
H32D	0.2546	0.5947	0.6192	0.178*	0.211 (17)
H32E	0.3364	0.6610	0.6248	0.178*	0.211 (17)
H32F	0.2932	0.6344	0.5644	0.178*	0.211 (17)
C33	0.2773 (9)	0.6582 (12)	0.6390 (5)	0.145 (5)	0.789 (17)
H33A	0.3016	0.6029	0.6168	0.218*	0.789 (17)
H33B	0.2322	0.6267	0.6562	0.218*	0.789 (17)
H33C	0.3168	0.6848	0.6681	0.218*	0.789 (17)
C33'	0.231 (4)	0.785 (5)	0.659 (2)	0.179 (16)	0.211 (17)
H33D	0.2033	0.7279	0.6778	0.269*	0.211 (17)
H33E	0.1998	0.8516	0.6580	0.269*	0.211 (17)
H33F	0.2833	0.7977	0.6791	0.269*	0.211 (17)
O4	0.5316 (3)	0.5614 (4)	0.71619 (19)	0.1447 (16)
N16	0.5668 (2)	0.3888 (3)	0.69505 (16)	0.0867 (11)
C34	0.5405 (3)	0.2784 (4)	0.6781 (2)	0.1134 (18)
H34A	0.4825	0.2776	0.6701	0.170*
H34B	0.5559	0.2275	0.7084	0.170*
H34C	0.5656	0.2570	0.6447	0.170*
C35	0.6527 (4)	0.4112 (6)	0.7073 (3)	0.159 (3)
H35A	0.6677	0.4009	0.7472	0.238*
H35B	0.6638	0.4860	0.6970	0.238*
H35C	0.6834	0.3616	0.6859	0.238*
C36	0.5142 (3)	0.4681 (5)	0.6997 (2)	0.0985 (16)
H36	0.4597	0.4524	0.6898	0.118*
O5	−0.1045 (4)	0.2077 (6)	0.7441 (3)	0.183 (3)
N17	0.0247 (4)	0.2275 (6)	0.7772 (2)	0.142 (2)
C37	0.1040 (6)	0.1765 (9)	0.7771 (4)	0.218 (5)
H37A	0.0982	0.1037	0.7611	0.328*
H37B	0.1288	0.1716	0.8154	0.328*
H37C	0.1376	0.2203	0.7547	0.328*
C38	0.0197 (8)	0.3267 (9)	0.8067 (4)	0.274 (7)
H38A	−0.0324	0.3599	0.7968	0.412*
H38B	0.0617	0.3758	0.7966	0.412*
H38C	0.0263	0.3125	0.8468	0.412*
C39	−0.0349 (6)	0.1761 (8)	0.7495 (3)	0.157 (3)
H39	−0.0234	0.1094	0.7324	0.188*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0482 (2)	0.0487 (2)	0.0677 (3)	0.00276 (18)	−0.00461 (19)	0.0070 (2)
S1	0.0513 (5)	0.0683 (6)	0.0803 (7)	−0.0056 (5)	0.0065 (5)	0.0068 (5)
S2	0.0839 (7)	0.0961 (9)	0.0587 (6)	0.0006 (6)	0.0016 (6)	−0.0176 (6)
O1	0.143 (3)	0.101 (2)	0.089 (2)	−0.016 (2)	0.007 (2)	0.0266 (19)
O2	0.127 (6)	0.121 (6)	0.089 (6)	−0.023 (4)	0.007 (4)	−0.027 (5)
O2'	0.132 (8)	0.114 (8)	0.130 (7)	−0.023 (6)	0.011 (5)	−0.015 (5)
N1	0.107 (3)	0.057 (2)	0.112 (3)	0.019 (2)	0.011 (3)	−0.011 (2)
N2	0.0547 (19)	0.100 (3)	0.093 (3)	−0.0179 (19)	−0.0151 (18)	0.047 (2)
N3	0.062 (2)	0.072 (2)	0.137 (4)	−0.0155 (18)	−0.025 (2)	0.051 (2)
N4	0.0589 (18)	0.0546 (19)	0.068 (2)	−0.0095 (15)	0.0191 (16)	−0.0158 (16)
N5	0.0584 (18)	0.0449 (17)	0.063 (2)	−0.0006 (14)	0.0132 (15)	−0.0074 (14)
N6	0.096 (3)	0.065 (2)	0.082 (3)	0.0124 (19)	0.002 (2)	0.0014 (19)
N7	0.083 (2)	0.0533 (19)	0.072 (2)	0.0054 (17)	0.0118 (19)	−0.0053 (16)
N8	0.0486 (17)	0.084 (2)	0.092 (3)	−0.0047 (17)	0.0004 (17)	0.019 (2)
N9	0.0489 (17)	0.0507 (17)	0.072 (2)	0.0024 (14)	0.0021 (15)	0.0028 (15)
N10	0.0582 (19)	0.0532 (18)	0.065 (2)	0.0076 (15)	0.0028 (16)	−0.0031 (14)
N11	0.0469 (16)	0.0503 (17)	0.0596 (18)	−0.0031 (13)	0.0031 (14)	−0.0076 (14)
N12	0.0489 (18)	0.072 (2)	0.079 (2)	−0.0041 (16)	−0.0030 (17)	−0.0069 (18)
N13	0.0538 (19)	0.081 (2)	0.079 (2)	−0.0088 (17)	−0.0022 (17)	0.0008 (19)
N14	0.076 (2)	0.091 (3)	0.078 (2)	−0.016 (2)	0.005 (2)	0.012 (2)
C1	0.073 (3)	0.114 (4)	0.058 (3)	−0.033 (3)	0.019 (2)	−0.044 (3)
C2	0.067 (2)	0.082 (3)	0.054 (2)	−0.027 (2)	0.024 (2)	−0.036 (2)
C3	0.060 (2)	0.061 (2)	0.068 (3)	−0.0095 (19)	0.019 (2)	−0.013 (2)
C4	0.084 (3)	0.109 (4)	0.051 (2)	−0.020 (3)	0.000 (2)	−0.002 (2)
C5	0.090 (3)	0.097 (4)	0.082 (4)	0.008 (3)	0.000 (3)	0.011 (3)
C6	0.075 (3)	0.081 (3)	0.086 (3)	0.006 (2)	0.004 (3)	0.008 (3)
C7	0.068 (2)	0.057 (2)	0.071 (3)	−0.0008 (19)	0.011 (2)	−0.003 (2)
C8	0.053 (2)	0.051 (2)	0.057 (2)	−0.0100 (17)	0.0117 (17)	−0.0060 (17)
C9	0.050 (2)	0.046 (2)	0.066 (3)	−0.0098 (16)	0.0167 (18)	−0.0123 (18)
C10	0.049 (2)	0.042 (2)	0.083 (3)	−0.0053 (16)	0.0149 (19)	−0.0127 (19)
C11	0.058 (2)	0.058 (2)	0.056 (2)	−0.0013 (18)	0.0090 (18)	−0.0050 (18)
C12	0.054 (2)	0.043 (2)	0.085 (3)	−0.0006 (16)	0.010 (2)	−0.004 (2)
C13	0.086 (3)	0.058 (3)	0.095 (3)	0.011 (2)	0.012 (3)	−0.014 (2)
C14	0.108 (3)	0.064 (3)	0.064 (3)	0.007 (2)	0.022 (2)	0.001 (2)
C15	0.145 (5)	0.077 (3)	0.064 (3)	−0.022 (3)	0.005 (3)	0.005 (2)
C16	0.052 (2)	0.054 (2)	0.075 (3)	−0.0130 (17)	0.0182 (19)	−0.0096 (19)
C17	0.046 (2)	0.053 (2)	0.064 (2)	0.0022 (17)	0.0039 (17)	−0.0054 (18)
C18	0.051 (2)	0.059 (2)	0.064 (2)	0.0072 (18)	−0.0008 (18)	−0.0040 (19)
C19	0.070 (3)	0.072 (3)	0.074 (3)	0.006 (2)	0.003 (2)	0.006 (2)
C20	0.085 (3)	0.095 (3)	0.075 (3)	0.016 (3)	−0.003 (3)	0.011 (3)
C21	0.069 (3)	0.101 (4)	0.094 (4)	0.019 (3)	−0.022 (3)	0.004 (3)
C22	0.053 (2)	0.090 (3)	0.091 (3)	0.009 (2)	−0.012 (2)	0.000 (3)
C23	0.049 (2)	0.067 (2)	0.069 (3)	0.0064 (18)	−0.0037 (18)	−0.004 (2)
C24	0.0419 (19)	0.062 (2)	0.071 (3)	−0.0026 (17)	0.0000 (18)	−0.0069 (19)
C25	0.0461 (19)	0.055 (2)	0.057 (2)	0.0054 (17)	−0.0011 (17)	−0.0091 (18)
C26	0.050 (2)	0.064 (2)	0.071 (3)	−0.0088 (19)	0.0049 (19)	0.001 (2)
C27	0.056 (2)	0.055 (2)	0.063 (2)	0.0016 (18)	0.0022 (18)	−0.0063 (19)
C28	0.060 (2)	0.076 (3)	0.076 (3)	−0.009 (2)	−0.001 (2)	0.007 (2)
C29	0.060 (3)	0.110 (4)	0.100 (4)	−0.021 (3)	0.019 (2)	−0.003 (3)
C30	0.129 (18)	0.090 (16)	0.20 (2)	−0.002 (13)	−0.002 (15)	0.022 (15)
C30'	0.040 (7)	0.075 (12)	0.121 (14)	−0.025 (7)	0.000 (7)	0.010 (10)
O6W	0.149 (3)	0.107 (3)	0.118 (3)	0.025 (2)	0.014 (2)	0.030 (2)
O3	0.112 (10)	0.267 (16)	0.172 (12)	−0.044 (10)	−0.017 (9)	0.044 (13)
O3'	0.065 (16)	0.097 (16)	0.039 (12)	−0.001 (12)	0.013 (11)	0.042 (11)
N15	0.099 (7)	0.098 (7)	0.097 (7)	−0.019 (6)	0.019 (5)	−0.018 (6)
N15'	0.083 (17)	0.088 (17)	0.073 (17)	0.005 (14)	−0.006 (14)	0.063 (14)
C31	0.075 (4)	0.114 (6)	0.097 (7)	−0.007 (4)	0.002 (4)	0.017 (5)
C31'	0.10 (2)	0.22 (3)	0.18 (4)	−0.05 (2)	−0.01 (3)	−0.03 (3)
C32	0.167 (9)	0.139 (9)	0.164 (12)	0.019 (7)	0.051 (9)	−0.015 (8)
C32'	0.087 (17)	0.076 (18)	0.20 (3)	0.023 (14)	0.03 (2)	0.03 (2)
C33	0.165 (10)	0.139 (9)	0.126 (8)	−0.032 (7)	−0.024 (8)	0.072 (8)
C33'	0.18 (3)	0.19 (3)	0.17 (3)	0.00 (3)	0.05 (3)	0.02 (3)
O4	0.184 (4)	0.101 (3)	0.140 (3)	0.006 (3)	−0.035 (3)	−0.012 (3)
N16	0.085 (3)	0.088 (3)	0.084 (3)	0.003 (2)	−0.005 (2)	−0.011 (2)
C34	0.125 (5)	0.082 (4)	0.131 (5)	−0.005 (3)	−0.003 (4)	−0.005 (3)
C35	0.090 (4)	0.219 (8)	0.164 (6)	0.011 (5)	−0.001 (4)	−0.063 (6)
C36	0.112 (4)	0.087 (4)	0.091 (4)	0.001 (3)	−0.025 (3)	−0.014 (3)
O5	0.159 (5)	0.235 (7)	0.155 (5)	−0.062 (5)	0.006 (4)	−0.016 (4)
N17	0.140 (5)	0.181 (6)	0.103 (4)	−0.072 (5)	−0.004 (4)	0.011 (4)
C37	0.170 (9)	0.332 (14)	0.152 (8)	−0.048 (9)	0.007 (7)	0.037 (8)
C38	0.365 (17)	0.237 (11)	0.221 (11)	−0.119 (11)	0.024 (10)	−0.119 (9)
C39	0.155 (7)	0.208 (9)	0.107 (5)	−0.064 (8)	0.018 (6)	0.010 (5)

Geometric parameters (Å, º)

Zn1—N2	1.978 (3)	C19—C20	1.381 (5)
Zn1—N9	2.012 (3)	C19—H19	0.9300
Zn1—N11	2.151 (3)	C20—C21	1.373 (6)
Zn1—N4	2.284 (3)	C20—H20	0.9300
Zn1—S2	2.6581 (12)	C21—C22	1.375 (6)
Zn1—S1	2.7394 (12)	C21—H21	0.9300
S1—C16	1.667 (4)	C22—C23	1.380 (5)
S2—C1	1.632 (6)	C22—H22	0.9300
O1—C15	1.373 (5)	C23—C24	1.450 (5)
O2—C30	1.382 (17)	C24—C25	1.451 (5)
O2'—C30'	1.323 (16)	C26—C27	1.413 (5)
N1—C1	1.323 (6)	C27—C28	1.396 (5)
N1—H1A	0.8600	C28—H28	0.9300
N1—H1B	0.8600	C29—C30'	1.498 (13)
N2—N3	1.239 (4)	C29—C30	1.501 (16)
N2—C1	1.500 (5)	C29—H29A	0.9700
N3—C2	1.442 (5)	C29—H29B	0.9700
N4—C10	1.326 (4)	C30—H30A	0.9700
N4—C12	1.344 (5)	C30—H30B	0.9700
N5—C9	1.330 (4)	C30'—H30C	0.9700
N5—C11	1.340 (4)	C30'—H30D	0.9700
N6—C13	1.312 (5)	O3—C31	1.202 (17)
N6—N7	1.375 (4)	O3'—C31'	1.35 (8)
N7—C11	1.349 (5)	N15—C31	1.277 (18)
N7—C14	1.442 (5)	N15—C33	1.447 (17)
N8—C16	1.336 (5)	N15—C32	1.45 (2)
N8—H8NB	0.8600	N15'—C33'	1.38 (8)
N8—H8NA	0.8600	N15'—C32'	1.40 (7)
N9—N10	1.348 (4)	N15'—C31'	1.76 (7)
N9—C16	1.360 (4)	C31—H31	0.9300
N10—C17	1.324 (4)	C31'—H31'	0.9300
N11—C25	1.329 (4)	C32—H32A	0.9600
N11—C27	1.352 (4)	C32—H32B	0.9600
N12—C24	1.320 (5)	C32—H32C	0.9600
N12—C26	1.342 (5)	C32'—H32D	0.9600
N13—C26	1.345 (5)	C32'—H32E	0.9600
N13—N14	1.372 (4)	C32'—H32F	0.9600
N13—C29	1.474 (5)	C33—H33A	0.9600
N14—C28	1.329 (5)	C33—H33B	0.9600
C2—C10	1.442 (5)	C33—H33C	0.9600
C2—C3	1.453 (5)	C33'—H33D	0.9600
C3—C4	1.391 (6)	C33'—H33E	0.9600
C3—C8	1.400 (5)	C33'—H33F	0.9600
C4—C5	1.373 (6)	O4—C36	1.220 (5)
C4—H4	0.9300	N16—C36	1.307 (6)
C5—C6	1.369 (6)	N16—C35	1.447 (6)
C5—H5	0.9300	N16—C34	1.450 (6)
C6—C7	1.374 (6)	C34—H34A	0.9600
C6—H6	0.9300	C34—H34B	0.9600
C7—C8	1.380 (5)	C34—H34C	0.9600
C7—H7	0.9300	C35—H35A	0.9600
C8—C9	1.455 (5)	C35—H35B	0.9600
C9—C10	1.434 (5)	C35—H35C	0.9600
C11—C12	1.420 (5)	C36—H36	0.9300
C12—C13	1.423 (6)	O5—C39	1.208 (10)
C13—H13	0.9300	N17—C39	1.292 (9)
C14—C15	1.515 (6)	N17—C38	1.394 (11)
C14—H14A	0.9700	N17—C37	1.448 (10)
C14—H14B	0.9700	C37—H37A	0.9600
C15—H15A	0.9700	C37—H37B	0.9600
C15—H15B	0.9700	C37—H37C	0.9600
C17—C25	1.447 (5)	C38—H38A	0.9600
C17—C18	1.480 (5)	C38—H38B	0.9600
C18—C19	1.374 (5)	C38—H38C	0.9600
C18—C23	1.411 (5)	C39—H39	0.9300
N2—Zn1—N9	160.95 (12)	C21—C20—C19	122.0 (4)
N2—Zn1—N11	110.31 (12)	C21—C20—H20	119.0
N9—Zn1—N11	88.19 (11)	C19—C20—H20	119.0
N2—Zn1—N4	86.21 (16)	C20—C21—C22	121.0 (4)
N9—Zn1—N4	97.22 (12)	C20—C21—H21	119.5
N11—Zn1—N4	94.34 (10)	C22—C21—H21	119.5
N2—Zn1—S2	65.89 (13)	C21—C22—C23	118.7 (4)
N9—Zn1—S2	110.76 (9)	C21—C22—H22	120.7
N11—Zn1—S2	91.04 (8)	C23—C22—H22	120.7
N4—Zn1—S2	151.67 (9)	C22—C23—C18	119.6 (4)
N2—Zn1—S1	98.68 (9)	C22—C23—C24	131.6 (4)
N9—Zn1—S1	62.63 (8)	C18—C23—C24	108.8 (3)
N11—Zn1—S1	150.77 (8)	N12—C24—C23	127.7 (3)
N4—Zn1—S1	91.11 (8)	N12—C24—C25	124.4 (3)
S2—Zn1—S1	97.64 (4)	C23—C24—C25	107.9 (3)
C16—S1—Zn1	73.63 (13)	N11—C25—C17	129.5 (3)
C1—S2—Zn1	77.05 (16)	N11—C25—C24	122.6 (3)
C1—N1—H1A	120.0	C17—C25—C24	107.9 (3)
C1—N1—H1B	120.0	N12—C26—N13	127.2 (3)
H1A—N1—H1B	120.0	N12—C26—C27	126.4 (4)
N3—N2—C1	105.7 (4)	N13—C26—C27	106.4 (3)
N3—N2—Zn1	148.2 (4)	N11—C27—C28	134.0 (3)
C1—N2—Zn1	105.9 (3)	N11—C27—C26	121.3 (3)
N2—N3—C2	105.6 (4)	C28—C27—C26	104.7 (3)
C10—N4—C12	113.6 (3)	N14—C28—C27	111.7 (4)
C10—N4—Zn1	114.3 (2)	N14—C28—H28	124.1
C12—N4—Zn1	131.9 (3)	C27—C28—H28	124.1
C9—N5—C11	110.8 (3)	N13—C29—C30'	108.9 (7)
C13—N6—N7	106.5 (3)	N13—C29—C30	113.7 (11)
C11—N7—N6	110.6 (3)	C30'—C29—C30	6.2 (14)
C11—N7—C14	128.8 (3)	N13—C29—H29A	108.8
N6—N7—C14	120.6 (3)	C30'—C29—H29A	107.7
C16—N8—H8NB	120.0	C30—C29—H29A	108.8
C16—N8—H8NA	120.0	N13—C29—H29B	108.8
H8NB—N8—H8NA	120.0	C30'—C29—H29B	114.7
N10—N9—C16	113.9 (3)	C30—C29—H29B	108.8
N10—N9—Zn1	136.4 (2)	H29A—C29—H29B	107.7
C16—N9—Zn1	109.3 (2)	O2—C30—C29	110.3 (14)
C17—N10—N9	115.3 (3)	O2—C30—H30A	109.6
C25—N11—C27	114.0 (3)	C29—C30—H30A	109.6
C25—N11—Zn1	119.0 (2)	O2—C30—H30B	109.6
C27—N11—Zn1	126.9 (2)	C29—C30—H30B	109.6
C24—N12—C26	111.3 (3)	H30A—C30—H30B	108.1
C26—N13—N14	111.8 (3)	O2'—C30'—C29	115.2 (11)
C26—N13—C29	128.3 (4)	O2'—C30'—H30C	108.5
N14—N13—C29	119.7 (4)	C29—C30'—H30C	108.5
C28—N14—N13	105.4 (3)	O2'—C30'—H30D	108.5
N1—C1—N2	124.6 (5)	C29—C30'—H30D	108.5
N1—C1—S2	124.2 (3)	H30C—C30'—H30D	107.5
N2—C1—S2	111.2 (4)	C31—N15—C33	120.3 (15)
N3—C2—C10	135.5 (4)	C31—N15—C32	121.3 (14)
N3—C2—C3	116.4 (4)	C33—N15—C32	118.4 (15)
C10—C2—C3	108.1 (3)	C33'—N15'—C32'	112 (3)
C4—C3—C8	120.0 (4)	C33'—N15'—C31'	103 (5)
C4—C3—C2	132.1 (4)	C32'—N15'—C31'	142 (5)
C8—C3—C2	107.9 (3)	O3—C31—N15	122.5 (15)
C5—C4—C3	118.7 (4)	O3—C31—H31	118.8
C5—C4—H4	120.6	N15—C31—H31	118.8
C3—C4—H4	120.6	O3'—C31'—N15'	95 (4)
C6—C5—C4	120.7 (4)	O3'—C31'—H31'	132.7
C6—C5—H5	119.7	N15'—C31'—H31'	132.7
C4—C5—H5	119.7	N15'—C32'—H32D	109.5
C5—C6—C7	121.9 (4)	N15'—C32'—H32E	109.5
C5—C6—H6	119.0	H32D—C32'—H32E	109.5
C7—C6—H6	119.0	N15'—C32'—H32F	109.5
C6—C7—C8	118.2 (4)	H32D—C32'—H32F	109.5
C6—C7—H7	120.9	H32E—C32'—H32F	109.5
C8—C7—H7	120.9	N15'—C33'—H33D	109.5
C7—C8—C3	120.5 (4)	N15'—C33'—H33E	109.5
C7—C8—C9	130.6 (3)	H33D—C33'—H33E	109.5
C3—C8—C9	109.0 (3)	N15'—C33'—H33F	109.5
N5—C9—C10	124.9 (3)	H33D—C33'—H33F	109.5
N5—C9—C8	127.6 (3)	H33E—C33'—H33F	109.5
C10—C9—C8	107.6 (3)	C36—N16—C35	119.5 (5)
N4—C10—C9	122.9 (4)	C36—N16—C34	121.0 (4)
N4—C10—C2	129.5 (3)	C35—N16—C34	119.5 (5)
C9—C10—C2	107.5 (3)	N16—C34—H34A	109.5
N5—C11—N7	126.3 (3)	N16—C34—H34B	109.5
N5—C11—C12	125.8 (3)	H34A—C34—H34B	109.5
N7—C11—C12	107.9 (3)	N16—C34—H34C	109.5
N4—C12—C11	121.9 (3)	H34A—C34—H34C	109.5
N4—C12—C13	135.2 (4)	H34B—C34—H34C	109.5
C11—C12—C13	102.8 (4)	N16—C35—H35A	109.5
N6—C13—C12	112.2 (4)	N16—C35—H35B	109.5
N6—C13—H13	123.9	H35A—C35—H35B	109.5
C12—C13—H13	123.9	N16—C35—H35C	109.5
N7—C14—C15	112.8 (4)	H35A—C35—H35C	109.5
N7—C14—H14A	109.0	H35B—C35—H35C	109.5
C15—C14—H14A	109.0	O4—C36—N16	124.6 (5)
N7—C14—H14B	109.0	O4—C36—H36	117.7
C15—C14—H14B	109.0	N16—C36—H36	117.7
H14A—C14—H14B	107.8	C39—N17—C38	126.1 (10)
O1—C15—C14	112.1 (4)	C39—N17—C37	116.3 (9)
O1—C15—H15A	109.2	C38—N17—C37	117.6 (8)
C14—C15—H15A	109.2	N17—C37—H37A	109.5
O1—C15—H15B	109.2	N17—C37—H37B	109.5
C14—C15—H15B	109.2	H37A—C37—H37B	109.5
H15A—C15—H15B	107.9	N17—C37—H37C	109.5
N8—C16—N9	120.7 (3)	H37A—C37—H37C	109.5
N8—C16—S1	125.2 (3)	H37B—C37—H37C	109.5
N9—C16—S1	114.2 (3)	N17—C38—H38A	109.5
N10—C17—C25	131.4 (3)	N17—C38—H38B	109.5
N10—C17—C18	121.6 (3)	H38A—C38—H38B	109.5
C25—C17—C18	107.0 (3)	N17—C38—H38C	109.5
C19—C18—C23	121.6 (3)	H38A—C38—H38C	109.5
C19—C18—C17	130.1 (3)	H38B—C38—H38C	109.5
C23—C18—C17	108.3 (3)	O5—C39—N17	125.3 (11)
C18—C19—C20	117.2 (4)	O5—C39—H39	117.4
C18—C19—H19	121.4	N17—C39—H39	117.4
C20—C19—H19	121.4
N2—Zn1—S1—C16	−178.87 (18)	N3—C2—C10—C9	−178.1 (4)
N9—Zn1—S1—C16	−2.76 (16)	C3—C2—C10—C9	−0.2 (4)
N11—Zn1—S1—C16	−6.1 (2)	C9—N5—C11—N7	179.7 (3)
N4—Zn1—S1—C16	94.79 (16)	C9—N5—C11—C12	−0.4 (5)
S2—Zn1—S1—C16	−112.23 (14)	N6—N7—C11—N5	−178.3 (3)
N2—Zn1—S2—C1	1.10 (17)	C14—N7—C11—N5	0.3 (6)
N9—Zn1—S2—C1	−158.59 (17)	N6—N7—C11—C12	1.8 (4)
N11—Zn1—S2—C1	112.95 (16)	C14—N7—C11—C12	−179.7 (4)
N4—Zn1—S2—C1	11.8 (2)	C10—N4—C12—C11	1.0 (5)
S1—Zn1—S2—C1	−95.03 (15)	Zn1—N4—C12—C11	175.7 (2)
N9—Zn1—N2—N3	−90.6 (7)	C10—N4—C12—C13	−178.5 (4)
N11—Zn1—N2—N3	103.8 (5)	Zn1—N4—C12—C13	−3.8 (6)
N4—Zn1—N2—N3	10.6 (5)	N5—C11—C12—N4	−0.8 (6)
S2—Zn1—N2—N3	−174.5 (5)	N7—C11—C12—N4	179.1 (3)
S1—Zn1—N2—N3	−79.9 (5)	N5—C11—C12—C13	178.8 (4)
N9—Zn1—N2—C1	82.7 (5)	N7—C11—C12—C13	−1.2 (4)
N11—Zn1—N2—C1	−82.9 (2)	N7—N6—C13—C12	0.7 (5)
N4—Zn1—N2—C1	−176.1 (2)	N4—C12—C13—N6	179.9 (4)
S2—Zn1—N2—C1	−1.21 (19)	C11—C12—C13—N6	0.3 (5)
S1—Zn1—N2—C1	93.3 (2)	C11—N7—C14—C15	108.3 (5)
C1—N2—N3—C2	179.6 (3)	N6—N7—C14—C15	−73.3 (5)
Zn1—N2—N3—C2	−7.1 (6)	N7—C14—C15—O1	−70.0 (5)
N2—Zn1—N4—C10	−6.5 (2)	N10—N9—C16—N8	1.2 (5)
N9—Zn1—N4—C10	154.7 (2)	Zn1—N9—C16—N8	175.4 (3)
N11—Zn1—N4—C10	−116.6 (2)	N10—N9—C16—S1	−179.7 (2)
S2—Zn1—N4—C10	−16.3 (3)	Zn1—N9—C16—S1	−5.5 (3)
S1—Zn1—N4—C10	92.1 (2)	Zn1—S1—C16—N8	−177.0 (4)
N2—Zn1—N4—C12	178.8 (3)	Zn1—S1—C16—N9	4.0 (2)
N9—Zn1—N4—C12	−20.1 (3)	N9—N10—C17—C25	0.4 (5)
N11—Zn1—N4—C12	68.6 (3)	N9—N10—C17—C18	179.0 (3)
S2—Zn1—N4—C12	169.0 (2)	N10—C17—C18—C19	1.4 (6)
S1—Zn1—N4—C12	−82.6 (3)	C25—C17—C18—C19	−179.7 (4)
C13—N6—N7—C11	−1.6 (5)	N10—C17—C18—C23	−178.4 (3)
C13—N6—N7—C14	179.8 (4)	C25—C17—C18—C23	0.5 (4)
N2—Zn1—N9—N10	−172.4 (4)	C23—C18—C19—C20	0.2 (6)
N11—Zn1—N9—N10	−5.9 (3)	C17—C18—C19—C20	−179.6 (4)
N4—Zn1—N9—N10	88.3 (3)	C18—C19—C20—C21	0.8 (7)
S2—Zn1—N9—N10	−96.3 (3)	C19—C20—C21—C22	−1.1 (8)
S1—Zn1—N9—N10	175.8 (4)	C20—C21—C22—C23	0.4 (7)
N2—Zn1—N9—C16	15.3 (6)	C21—C22—C23—C18	0.6 (6)
N11—Zn1—N9—C16	−178.2 (2)	C21—C22—C23—C24	177.7 (4)
N4—Zn1—N9—C16	−84.1 (2)	C19—C18—C23—C22	−0.9 (6)
S2—Zn1—N9—C16	91.4 (2)	C17—C18—C23—C22	178.9 (3)
S1—Zn1—N9—C16	3.4 (2)	C19—C18—C23—C24	−178.7 (3)
C16—N9—N10—C17	176.9 (3)	C17—C18—C23—C24	1.2 (4)
Zn1—N9—N10—C17	4.8 (5)	C26—N12—C24—C23	−179.8 (4)
N2—Zn1—N11—C25	178.5 (3)	C26—N12—C24—C25	1.1 (5)
N9—Zn1—N11—C25	3.1 (3)	C22—C23—C24—N12	1.0 (7)
N4—Zn1—N11—C25	−94.0 (3)	C18—C23—C24—N12	178.4 (4)
S2—Zn1—N11—C25	113.9 (2)	C22—C23—C24—C25	−179.8 (4)
S1—Zn1—N11—C25	6.1 (3)	C18—C23—C24—C25	−2.4 (4)
N2—Zn1—N11—C27	1.9 (3)	C27—N11—C25—C17	176.3 (3)
N9—Zn1—N11—C27	−173.4 (3)	Zn1—N11—C25—C17	−0.7 (5)
N4—Zn1—N11—C27	89.5 (3)	C27—N11—C25—C24	−2.6 (5)
S2—Zn1—N11—C27	−62.7 (3)	Zn1—N11—C25—C24	−179.5 (2)
S1—Zn1—N11—C27	−170.4 (2)	N10—C17—C25—N11	−2.2 (6)
C26—N13—N14—C28	0.9 (5)	C18—C17—C25—N11	179.0 (3)
C29—N13—N14—C28	176.3 (4)	N10—C17—C25—C24	176.8 (4)
N3—N2—C1—N1	−0.5 (5)	C18—C17—C25—C24	−2.0 (4)
Zn1—N2—C1—N1	−176.8 (3)	N12—C24—C25—N11	1.1 (6)
N3—N2—C1—S2	178.3 (3)	C23—C24—C25—N11	−178.2 (3)
Zn1—N2—C1—S2	1.9 (3)	N12—C24—C25—C17	−178.0 (3)
Zn1—S2—C1—N1	177.3 (4)	C23—C24—C25—C17	2.7 (4)
Zn1—S2—C1—N2	−1.4 (2)	C24—N12—C26—N13	177.8 (4)
N2—N3—C2—C10	−2.3 (6)	C24—N12—C26—C27	−1.7 (5)
N2—N3—C2—C3	179.8 (3)	N14—N13—C26—N12	179.5 (4)
N3—C2—C3—C4	−1.8 (6)	C29—N13—C26—N12	4.7 (7)
C10—C2—C3—C4	179.8 (4)	N14—N13—C26—C27	−0.8 (4)
N3—C2—C3—C8	178.8 (3)	C29—N13—C26—C27	−175.7 (4)
C10—C2—C3—C8	0.4 (4)	C25—N11—C27—C28	−177.8 (4)
C8—C3—C4—C5	−0.8 (6)	Zn1—N11—C27—C28	−1.1 (6)
C2—C3—C4—C5	179.8 (4)	C25—N11—C27—C26	2.0 (5)
C3—C4—C5—C6	0.9 (7)	Zn1—N11—C27—C26	178.7 (3)
C4—C5—C6—C7	−0.4 (7)	N12—C26—C27—N11	0.2 (6)
C5—C6—C7—C8	−0.1 (6)	N13—C26—C27—N11	−179.5 (3)
C6—C7—C8—C3	0.2 (5)	N12—C26—C27—C28	−179.9 (4)
C6—C7—C8—C9	−179.5 (4)	N13—C26—C27—C28	0.4 (4)
C4—C3—C8—C7	0.3 (5)	N13—N14—C28—C27	−0.6 (5)
C2—C3—C8—C7	179.8 (3)	N11—C27—C28—N14	180.0 (4)
C4—C3—C8—C9	−180.0 (3)	C26—C27—C28—N14	0.1 (5)
C2—C3—C8—C9	−0.4 (4)	C26—N13—C29—C30'	83.7 (9)
C11—N5—C9—C10	1.4 (5)	N14—N13—C29—C30'	−90.8 (8)
C11—N5—C9—C8	−180.0 (3)	C26—N13—C29—C30	87.9 (11)
C7—C8—C9—N5	1.2 (6)	N14—N13—C29—C30	−86.6 (11)
C3—C8—C9—N5	−178.5 (3)	N13—C29—C30—O2	−60 (2)
C7—C8—C9—C10	−180.0 (3)	C30'—C29—C30—O2	−20 (14)
C3—C8—C9—C10	0.3 (4)	N13—C29—C30'—O2'	63.4 (14)
C12—N4—C10—C9	0.0 (5)	C30—C29—C30'—O2'	−78 (15)
Zn1—N4—C10—C9	−175.8 (2)	C33—N15—C31—O3	−179.3 (15)
C12—N4—C10—C2	179.9 (3)	C32—N15—C31—O3	3 (2)
Zn1—N4—C10—C2	4.2 (5)	C33'—N15'—C31'—O3'	178 (4)
N5—C9—C10—N4	−1.3 (5)	C32'—N15'—C31'—O3'	23 (7)
C8—C9—C10—N4	179.8 (3)	C35—N16—C36—O4	−3.1 (9)
N5—C9—C10—C2	178.8 (3)	C34—N16—C36—O4	176.5 (5)
C8—C9—C10—C2	−0.1 (4)	C38—N17—C39—O5	1.6 (14)
N3—C2—C10—N4	1.9 (7)	C37—N17—C39—O5	−178.3 (8)
C3—C2—C10—N4	179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8A···S1^i	0.86	2.50	3.340 (3)	166
N8—H8B···O6W	0.86	2.32	3.051 (5)	144
N1—H1B···N6^ii	0.86	2.40	3.258 (6)	172
N1—H1A···O4^iii	0.86	2.31	3.039 (6)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2.