{N,N′ Bis­[2 (methyl­sulfanyl)­phenyl]­pyridine 2,6 dicarboxamidato(2–)}­nickel(II)

(1)metal-organic papers Acta Crystallographica Section E. Structure Reports Online. {N,N0 -Bis[2-(methylsulfanyl)phenyl]pyridine2,6-dicarboxamidato(2±)}nickel(II). ISSN 1600-5368. Sheng-Gui Liu, Yi-Zhi Li,* Jing-Lin Zuo* and Xiao-Zeng You Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China. In the molecule of the title complex, [Ni(C21H17N3O2S2)], the Ni atom is coordinated by three N atoms and one S atom of the pyridine-2,6-dicarboxamide ligand. The geometry around the NiII atom is approximately square planar. The crystal structure is stabilized by weak ± and CÐH  O intermolecular interactions.. Received 2 July 2004 Accepted 13 July 2004 Online 24 July 2004. Correspondence e-mail: llyyjz@nju.edu.cn. Comment Key indicators Single-crystal X-ray study T = 293 K Ê Mean (C±C) = 0.005 A R factor = 0.052 wR factor = 0.132 Data-to-parameter ratio = 14.5 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.. # 2004 International Union of Crystallography Printed in Great Britain ± all rights reserved. Acta Cryst. (2004). E60, m1153±m1155. Nickel complexes with N,S-donor chelate ligands have received much attention in recent years. As well as being employed as models of metalloenzymes such as [NiFe]hydrogenases (Marganian et al., 1995), some of the complexes have been found to have pharmacological and catalytic properties (BruÈckner et al., 2000; Harrop et al., 2003). In order to develop further the coordination chemistry of nickel complexes with N,S-donor chelate ligands, we have synthesized a nickel complex based on the ligand N,N0 -bis[2(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamide, L2ÿ, which contains deprotonated carboxamide nitrogen and sulfur as donor atoms.. The title complex, (I), was obtained from reaction of L2ÿ and NiCl2 in DMF solution in high yield. The absence of (NH) (3170 cmÿ1) in the IR spectrum con®rms that the ligand is coordinated to the Ni atom in the deprotonated form. The C O stretching vibration for the complex is at 1635 cmÿ1, lower than that in the free ligand H2L (1676 cmÿ1). Such behavior is also observed in another deprotonated amide complex (Patra et al., 2000). Compared to the UV spectrum of the free ligand, there is a new absorption band at 342 nm for the complex, which is caused by a ligand-to-metal charge transfer transition. DOI: 10.1107/S1600536804017143. Liu, Li, Zuo and You. . [Ni(C21H17N3O2S2)]. m1153.

(2) metal-organic papers shorter than those reported for a C O bond [1.234 (6) and Ê ; Redmore et al., 1997]. Subtle changes within a 1.242 (6) A ligand framework may result in entirely different structures when coordinated to a metal center. An NiN6 compressed octahedral coordination for 2,6-bis(N-phenylcarbamoyl)pyridine has been reported (Patra & Mukherjee, 1999). The crystal packing of the title complex is shown in Fig. 2. Two adjacent molecules form a dimer in the head-to-head fashion by two weak interactions; one is an intermolecular ±  interaction between the pyridine ring and the C1±C6 Ê; benzene ring [the distance Cg1  Cg2i is 3.691 (16) A symmetry code: (i) ÿx, 2 ÿ y, ÿz; Cg1 is the center of the benzene ring and Cg2 is the center of the pyridine ring], and the other is an intermolecular weak interaction C15Ð H15  O1i (Table 2). In the dimer, the Ni1  Ni1i distance is Ê . In the crystal structure, these dimers form a 4.2943 (11) A two-dimensional layer through two further weak interactions (see Table 2). Figure 1. The molecular structure of (I), with anisotropic displacement ellipsoids drawn at the 30% probability level.. Figure 2. The packing of the complex. The dashed lines show weak ± and CÐ H  O interactions, as detailed in Table 2 and the main text.. The molecular structure of the title complex is shown in Fig. 1. It is a mononuclear complex. The geometry around the central Ni atom is approximately square planar (r.m.s. deviaÊ ). Three of the coordination sites are occupied tion = 0.022 A by N atoms from two amidate moieties and one pyridine ring; the fourth donor is an S atom. The C1±C6 benzene ring, the central pyridine ring and the two carboxamide groups are coplanar with the nickel coordination plane, which makes a dihedral angle of 75.74 (8) with the other benzene ring, C14± Ê ] is C19. The average NiÐNamide distance [1.8685 (2) A appreciably longer than that for NiÐNpy [py is pyridine; Ê ], because of the steric requirement of the rigid 1.821 (2) A ligand. This behavior has also been observed in an NiN3O square-planar complex (Kawamoto et al., 1998). The Ni1ÐS1 bond distance is shorter than that observed in another Ê ; BruÈckner et al., 2000]. complex [2.1988 (9) and 2.1740 (9) A The bond lengths for C7ÐO1 and C13ÐO2 are only slightly. m1154. Liu, Li, Zuo and You. . [Ni(C21H17N3O2S2)]. Experimental All the chemicals were of AR grade reagent. CH2Cl2 and DMF were dried over CaH2 and distilled before use. Pyridine-2,6-dicarboxylic acid (3.34 g, 20 mmol) was re¯uxed in 10 ml thionyl chloride for 8 h. Excess thionyl chloride was removed under vacuum. After cooling to room temperature, 2-(methylthio)aniline (5.56 g, 40 mmol) and triethylamine (3 ml) in CH2Cl2 (40 ml) were added to the solution of the residue in dry CH2Cl2 (30 ml). After the mixture had been stirred for 2 h at ambient temperature, the precipitated white solid was collected by ®ltration, washed with water and dried in vacuo. The product was recrystallized from ethanol to give the ligand H2L (yield: 7.40 g, 90.5%). Analysis calculated for C21H19N3O2S2: C 61.54, H 4.64, N 10.26%; found: C 61.62, H 4.63, N 10.29%. IR (KBr pellets, cmÿ1): 3450, 3170, 1676, 1655, 1585, 1533, 1458, 1257, 1073, 768. The ligand H2L (257 mg, 0.63 mmol) and NaH (30 mg, 1.25 mmol) in 10 ml N,N-dimethylformamide (DMF) were added to a solution of NiCl26H2O (74 mg, 0.315 mmol) in DMF (5 ml) with stirring. The resulting red solution was stirred for 15 min at room temperature. Exposure of the solution to the air for a week gave red single crystals suitable for structure determination (yield: 180 mg, 69.20%). Analysis calculated for C21H19N3NiO2S2: C 54.05, H 3.65, N 9.00%; found: C 54.13, H 3.63, N 9.04%. IR: (KBr pellets, cmÿ1): 3445, 1635, 1578, 1466, 1360, 750. UV (DMF): 342 nm. Crystal data Dx = 1.585 Mg mÿ3 Mo K radiation Cell parameters from 775 re¯ections  = 2.5±25.0  = 1.23 mmÿ1 T = 293 (2) K Prism, red 0.32  0.22  0.20 mm. [Ni(C21H17N3O2S2)] Mr = 466.21 Monoclinic, P21 =c Ê a = 11.430 (2) A Ê b = 11.406 (2) A Ê c = 15.087 (3) A

(3) = 96.765 (4) Ê3 V = 1953.2 (6) A Z=4. Data collection Bruker SMART APEX CCD areadetector diffractometer ' and ! scans Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin = 0.669, Tmax = 0.782 10243 measured re¯ections. 3834 independent re¯ections 3039 re¯ections with I > 2(I) Rint = 0.066 max = 26.0 h = ÿ8 ! 14 k = ÿ14 ! 13 l = ÿ18 ! 18. Acta Cryst. (2004). E60, m1153±m1155.

(4) metal-organic papers Re®nement w = 1/( 2(Fo2) + (0.07P)2 + 1.55P) where P = (Fo2 + 2Fc2)/3 (/)max < 0.001 Ê ÿ3 max = 0.87 e A Ê ÿ3 min = ÿ0.83 e A. Re®nement on F 2 R[F 2 > 2(F 2)] = 0.052 wR(F 2) = 0.132 S = 0.92 3834 re¯ections 264 parameters H-atom parameters constrained. Table 1. Ê ,  ). Selected geometric parameters (A Ni1ÐN2 Ni1ÐN1. 1.821 (3) 1.861 (3). Ni1ÐN3 Ni1ÐS1. 1.876 (3) 2.1535 (10). N2ÐNi1ÐN1 N2ÐNi1ÐN3 N1ÐNi1ÐN3. 83.88 (13) 83.42 (13) 167.19 (13). N2ÐNi1ÐS1 N1ÐNi1ÐS1 N3ÐNi1ÐS1. 173.58 (10) 89.88 (10) 102.85 (10). Table 2. Ê ,  ). Hydrogen-bonding geometry (A DÐH  A. DÐH. H  A. D  A. DÐH  A. C15ÐH15  O1i C11ÐH11  O2ii C18ÐH18  O2iii. 0.93 0.93 0.93. 2.36 2.77 2.32. 3.272 (6) 3.134 (5) 3.235 (5). 168 105 167. Symmetry codes: (i) ÿx; 2 ÿ y; ÿz; (ii) 1 ÿ x; 2 ÿ y; ÿz; (iii) 1 ÿ x; y ÿ 12; 12 ÿ z.. H atoms were positioned geometrically and constrained as riding Ê and Uiso(H) set to 1.2± atoms, with CÐH distances of 0.93±0.96 A 1.5Ueq of the parent atom.. Acta Cryst. (2004). E60, m1153±m1155. Data collection: SMART (Bruker, 2000); cell re®nement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to re®ne structure: SHELXTL; molecular graphics: SHELXTL and MERCURY (Version 1.2.1; Bruno et al., 2002); software used to prepare material for publication: SHELXTL.. This work was supported by The Major State Basic Research Development Program (G2000077500) and the National Natural Science Foundation of China (NSF20201006 and 90101028).. References BruÈckner, C., Retting, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100±6106. Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01), SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389±397. Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410±411. Kawamoto, T., Hamme, B. S., Ostrander, R., Rheingold, A. L. & Borovik, A. S. (1998). Inorg. Chem. 37, 3424±3427. Marganian, C. A., Vazir, H, Baidya, N., Olmstead, M. M. & Mascharak, P. K. (1995). J. Am. Chem. Soc. 117, 1584±1594. Patra, A. K. & Mukherjee, R. (1999). Inorg. Chem. 38, 1388±1393. Patra, A. K., Ray, M. & Mukherjee, R. (2000). Inorg. Chem. 39, 652±657. Redmore, S. M., Rickard, C. E. F., Webb, S. J. & Wright, L. J. (1997). Inorg. Chem. 36, 4743±4748.. Liu, Li, Zuo and You. . [Ni(C21H17N3O2S2)]. m1155.

(5) supporting information. supporting information Acta Cryst. (2004). E60, m1153–m1155. [https://doi.org/10.1107/S1600536804017143]. {N,N′-Bis[2-(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamidato(2–)}nickel(II) Sheng-Gui Liu, Yi-Zhi Li, Jing-Lin Zuo and Xiao-Zeng You [N,N′-Bis[2-(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamidato(2-)]nickel(II) Crystal data [Ni(C21H17N3O2S2)] Mr = 466.21 Monoclinic, P21/c Hall symbol: -P 2ybc a = 11.430 (2) Å b = 11.406 (2) Å c = 15.087 (3) Å β = 96.765 (4)° V = 1953.2 (6) Å3 Z=4. F(000) = 960 Dx = 1.585 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 775 reflections θ = 2.5–25.0° µ = 1.23 mm−1 T = 293 K Prism, red 0.32 × 0.22 × 0.2 mm. Data collection Bruker SMART APEX CCD area-detector diffractometer Radiation source: sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin = 0.669, Tmax = 0.782. 10243 measured reflections 3834 independent reflections 3039 reflections with I > 2σ(I) Rint = 0.066 θmax = 26.0°, θmin = 2.2° h = −8→14 k = −14→13 l = −18→18. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.052 wR(F2) = 0.132 S = 0.92 3834 reflections 264 parameters 0 restraints Primary atom site location: structure-invariant direct methods. Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/(σ2(Fo2) + (0.07P)2 + 1.55P) where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.87 e Å−3 Δρmin = −0.83 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.. Acta Cryst. (2004). E60, m1153–m1155. sup-1.

(6) supporting information 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.9201 (0.0134) x + 8.0106 (0.0134) y + 1.2127 (0.0248) z = 9.1849 (0.0082) * 0.0166 (0.0026) C14 * -0.0038 (0.0030) C15 * -0.0118 (0.0031) C16 * 0.0142 (0.0029) C17 * -0.0012 (0.0028) C18 * -0.0141 (0.0026) C19 Rms deviation of fitted atoms = 0.0118 - 5.8842 (0.0096) x + 8.8068 (0.0052) y + 6.4968 (0.0137) z = 7.0805 (0.0047) Angle to previous plane (with approximate e.s.d.) = 75.74 (0.08) * 0.0003 (0.0011) Ni1 * -0.0259 (0.0015) N1 * 0.0290 (0.0015) N2 * -0.0232 (0.0013) N3 * 0.0199 (0.0010) S1 Rms deviation of fitted atoms = 0.0221 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2). Ni1 N1 N2 N3 O1 O2 S1 S2 C1 C2 H2 C3 H3 C4 H4 C5 H5 C6 C7 C8 C9 H9 C10 H10 C11 H11 C12 C13 C14 C15 H15 C16. x. y. z. Uiso*/Ueq. 0.11727 (4) 0.0004 (3) 0.1857 (3) 0.2529 (3) −0.0412 (3) 0.4225 (2) 0.01872 (8) 0.42799 (11) −0.1000 (3) −0.1937 (4) −0.1935 −0.2864 (4) −0.3486 −0.2865 (4) −0.3503 −0.1944 (4) −0.1967 −0.0981 (3) 0.0188 (3) 0.1307 (3) 0.1812 (4) 0.1441 0.2878 (4) 0.3236 0.3425 (4) 0.4141 0.2877 (3) 0.3296 (3) 0.2836 (3) 0.2283 (4) 0.1706 0.2585 (4). 0.85609 (4) 0.8463 (2) 0.9577 (2) 0.8853 (3) 0.9124 (3) 0.9980 (2) 0.73777 (8) 0.69498 (11) 0.7145 (3) 0.6428 (4) 0.6042 0.6286 (4) 0.5792 0.6881 (4) 0.6795 0.7606 (4) 0.7997 0.7748 (3) 0.9089 (3) 0.9774 (3) 1.0539 (3) 1.0709 1.1040 (4) 1.1543 1.0811 (3) 1.1159 1.0050 (3) 0.9637 (3) 0.8375 (3) 0.8791 (4) 0.9366 0.8353 (4). 0.03563 (3) −0.06099 (19) −0.03580 (18) 0.11524 (19) −0.20783 (17) 0.12774 (17) 0.10977 (6) 0.12325 (7) 0.0249 (2) 0.0397 (3) 0.0940 −0.0257 (3) −0.0167 −0.1045 (3) −0.1482 −0.1211 (3) −0.1754 −0.0559 (2) −0.1355 (2) −0.1170 (2) −0.1727 (2) −0.2294 −0.1420 (3) −0.1791 −0.0575 (3) −0.0367 −0.0052 (2) 0.0877 (2) 0.2034 (2) 0.2732 (3) 0.2631 0.3586 (3). 0.03901 (17) 0.0404 (7) 0.0359 (6) 0.0414 (7) 0.0555 (7) 0.0563 (7) 0.0417 (2) 0.0619 (3) 0.0435 (9) 0.0592 (11) 0.071* 0.0679 (13) 0.082* 0.0658 (12) 0.079* 0.0545 (10) 0.065* 0.0424 (8) 0.0431 (9) 0.0411 (8) 0.0517 (10) 0.062* 0.0537 (10) 0.064* 0.0479 (9) 0.057* 0.0406 (8) 0.0429 (9) 0.0418 (9) 0.0534 (10) 0.064* 0.0584 (11). Acta Cryst. (2004). E60, m1153–m1155. sup-2.

(7) supporting information H16 C17 H17 C18 H18 C19 C20 H20A H20B H20C C21 H21A H21B H21C. 0.2206 0.3445 (4) 0.3668 0.3979 (4) 0.4548 0.3673 (3) 0.5131 (5) 0.5791 0.5410 0.4653 0.0950 (4) 0.0467 0.1678 0.1111. 0.8627 0.7513 (4) 0.7241 0.7070 (3) 0.6489 0.7488 (3) 0.5733 (5) 0.6004 0.5312 0.5224 0.5991 (4) 0.5390 0.6045 0.5800. 0.4058 0.3730 (3) 0.4307 0.3038 (3) 0.3145 0.2171 (2) 0.1658 (3) 0.2058 0.1173 0.1973 0.1111 (3) 0.1326 0.1498 0.0518. 0.070* 0.0542 (10) 0.065* 0.0492 (10) 0.059* 0.0414 (8) 0.0796 (15) 0.119* 0.119* 0.119* 0.0636 (12) 0.095* 0.095* 0.095*. Atomic displacement parameters (Å2). Ni1 N1 N2 N3 O1 O2 S1 S2 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21. U11. U22. U33. U12. U13. U23. 0.0459 (3) 0.0412 (17) 0.0427 (17) 0.0460 (18) 0.0620 (18) 0.0550 (17) 0.0457 (5) 0.0750 (8) 0.043 (2) 0.060 (3) 0.055 (3) 0.051 (3) 0.048 (2) 0.042 (2) 0.050 (2) 0.053 (2) 0.071 (3) 0.069 (3) 0.056 (2) 0.047 (2) 0.049 (2) 0.045 (2) 0.064 (3) 0.079 (3) 0.072 (3) 0.052 (2) 0.045 (2) 0.100 (4) 0.067 (3). 0.0394 (3) 0.0438 (17) 0.0354 (15) 0.0411 (16) 0.0656 (18) 0.0612 (18) 0.0422 (5) 0.0668 (7) 0.043 (2) 0.058 (3) 0.076 (3) 0.078 (3) 0.062 (3) 0.042 (2) 0.045 (2) 0.0378 (19) 0.049 (2) 0.048 (2) 0.042 (2) 0.0362 (18) 0.0387 (19) 0.044 (2) 0.051 (2) 0.059 (3) 0.054 (2) 0.048 (2) 0.045 (2) 0.074 (3) 0.053 (3). 0.0304 (3) 0.0344 (16) 0.0290 (14) 0.0342 (16) 0.0354 (14) 0.0487 (15) 0.0372 (5) 0.0452 (6) 0.045 (2) 0.061 (3) 0.074 (3) 0.066 (3) 0.050 (2) 0.0419 (19) 0.0336 (19) 0.0318 (17) 0.0339 (19) 0.045 (2) 0.046 (2) 0.0381 (18) 0.0395 (19) 0.0341 (18) 0.044 (2) 0.038 (2) 0.0338 (19) 0.045 (2) 0.0331 (18) 0.066 (3) 0.069 (3). 0.0006 (2) −0.0001 (14) 0.0026 (13) 0.0000 (14) 0.0029 (15) −0.0139 (15) −0.0018 (4) 0.0185 (6) −0.0007 (17) −0.009 (2) −0.021 (2) −0.011 (2) 0.000 (2) 0.0027 (17) 0.0099 (17) 0.0063 (17) 0.003 (2) −0.008 (2) −0.0046 (19) 0.0015 (17) 0.0009 (17) −0.0071 (17) 0.004 (2) 0.003 (2) −0.011 (2) 0.0008 (19) −0.0061 (17) 0.033 (3) 0.008 (2). −0.0012 (2) −0.0028 (13) 0.0016 (12) −0.0071 (13) −0.0089 (13) −0.0107 (14) 0.0044 (4) 0.0128 (6) 0.0041 (17) 0.012 (2) 0.011 (3) −0.001 (2) −0.0043 (19) 0.0003 (16) −0.0011 (17) 0.0035 (16) 0.0003 (19) 0.011 (2) 0.0067 (19) 0.0023 (16) −0.0008 (17) −0.0073 (16) 0.002 (2) 0.009 (2) −0.0059 (19) −0.0043 (18) −0.0024 (16) 0.014 (3) 0.001 (2). 0.00257 (18) 0.0005 (13) 0.0018 (12) 0.0071 (13) 0.0030 (13) 0.0020 (13) 0.0030 (4) 0.0093 (5) −0.0062 (16) −0.005 (2) −0.015 (3) −0.023 (3) −0.009 (2) −0.0097 (16) −0.0013 (16) 0.0001 (15) 0.0048 (17) 0.0068 (18) 0.0008 (17) −0.0036 (15) −0.0039 (16) 0.0025 (15) 0.0021 (18) −0.0007 (18) 0.0079 (18) 0.0076 (18) 0.0018 (16) 0.002 (3) 0.014 (2). Acta Cryst. (2004). E60, m1153–m1155. sup-3.

(8) supporting information Geometric parameters (Å, º) Ni1—N2 Ni1—N1 Ni1—N3 Ni1—S1 N1—C7 N1—C6 N2—C12 N2—C8 N3—C13 N3—C14 O1—C7 O2—C13 S1—C1 S1—C21 S2—C19 S2—C20 C1—C2 C1—C6 C2—C3 C2—H2 C3—C4 C3—H3 C4—C5 C4—H4 C5—C6 C5—H5. 1.821 (3) 1.861 (3) 1.876 (3) 2.1535 (10) 1.369 (5) 1.399 (5) 1.318 (5) 1.329 (4) 1.351 (5) 1.442 (4) 1.220 (4) 1.223 (4) 1.772 (4) 1.805 (4) 1.759 (4) 1.771 (5) 1.386 (6) 1.402 (5) 1.371 (6) 0.930 1.367 (7) 0.930 1.385 (6) 0.930 1.397 (5) 0.930. C7—C8 C8—C9 C9—C10 C9—H9 C10—C11 C10—H10 C11—C12 C11—H11 C12—C13 C14—C15 C14—C19 C15—C16 C15—H15 C16—C17 C16—H16 C17—C18 C17—H17 C18—C19 C18—H18 C20—H20A C20—H20B C20—H20C C21—H21A C21—H21B C21—H21C. 1.497 (5) 1.383 (5) 1.375 (6) 0.930 1.377 (5) 0.930 1.374 (5) 0.930 1.502 (5) 1.375 (6) 1.391 (5) 1.388 (6) 0.930 1.372 (6) 0.930 1.366 (6) 0.930 1.398 (5) 0.930 0.960 0.960 0.960 0.960 0.960 0.960. N2—Ni1—N1 N2—Ni1—N3 N1—Ni1—N3 N2—Ni1—S1 N1—Ni1—S1 N3—Ni1—S1 C7—N1—C6 C7—N1—Ni1 C6—N1—Ni1 C12—N2—C8 C12—N2—Ni1 C8—N2—Ni1 C13—N3—C14 C13—N3—Ni1 C14—N3—Ni1 C1—S1—C21 C1—S1—Ni1 C21—S1—Ni1 C19—S2—C20. 83.88 (13) 83.42 (13) 167.19 (13) 173.58 (10) 89.88 (10) 102.85 (10) 123.5 (3) 116.5 (3) 120.0 (2) 123.8 (3) 118.5 (2) 117.7 (3) 116.0 (3) 115.9 (2) 128.0 (2) 101.8 (2) 96.99 (13) 105.86 (16) 103.5 (2). C10—C9—H9 C8—C9—H9 C9—C10—C11 C9—C10—H10 C11—C10—H10 C12—C11—C10 C12—C11—H11 C10—C11—H11 N2—C12—C11 N2—C12—C13 C11—C12—C13 O2—C13—N3 O2—C13—C12 N3—C13—C12 C15—C14—C19 C15—C14—N3 C19—C14—N3 C14—C15—C16 C14—C15—H15. 120.9 120.9 121.4 (4) 119.3 119.3 117.6 (4) 121.2 121.2 120.1 (3) 111.8 (3) 128.1 (4) 128.0 (3) 121.6 (3) 110.3 (3) 120.5 (3) 119.5 (3) 120.1 (3) 120.1 (4) 120.0. Acta Cryst. (2004). E60, m1153–m1155. sup-4.

(9) supporting information C2—C1—C6 C2—C1—S1 C6—C1—S1 C3—C2—C1 C3—C2—H2 C1—C2—H2 C4—C3—C2 C4—C3—H3 C2—C3—H3 C3—C4—C5 C3—C4—H4 C5—C4—H4 C4—C5—C6 C4—C5—H5 C6—C5—H5 C5—C6—N1 C5—C6—C1 N1—C6—C1 O1—C7—N1 O1—C7—C8 N1—C7—C8 N2—C8—C9 N2—C8—C7 C9—C8—C7 C10—C9—C8. 121.4 (4) 120.8 (3) 117.7 (3) 120.0 (4) 120.0 120.0 119.2 (4) 120.4 120.4 122.1 (5) 119.0 119.0 119.6 (4) 120.2 120.2 126.9 (4) 117.7 (4) 115.4 (3) 128.8 (4) 121.8 (3) 109.3 (3) 118.7 (4) 112.6 (3) 128.7 (3) 118.3 (4). C16—C15—H15 C17—C16—C15 C17—C16—H16 C15—C16—H16 C18—C17—C16 C18—C17—H17 C16—C17—H17 C17—C18—C19 C17—C18—H18 C19—C18—H18 C14—C19—C18 C14—C19—S2 C18—C19—S2 S2—C20—H20A S2—C20—H20B H20A—C20—H20B S2—C20—H20C H20A—C20—H20C H20B—C20—H20C S1—C21—H21A S1—C21—H21B H21A—C21—H21B S1—C21—H21C H21A—C21—H21C H21B—C21—H21C. 120.0 119.6 (4) 120.2 120.2 120.9 (4) 119.6 119.6 120.3 (4) 119.8 119.8 118.6 (3) 117.6 (3) 123.8 (3) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5. Hydrogen-bond geometry (Å, º) D—H···A i. C15—H15···O1 C11—H11···O2ii C18—H18···O2iii. D—H. H···A. D···A. D—H···A. 0.93 0.93 0.93. 2.36 2.77 2.32. 3.272 (6) 3.134 (5) 3.235 (5). 168 105 167. Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, y−1/2, −z+1/2.. Acta Cryst. (2004). E60, m1153–m1155. sup-5.

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