metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages m619-m620

Bis[μ-N′-(adamantan-1-ylcarbon­yl)-2-oxidobenzohydrazidato(3−)]tetra­pyridine­trinickel(II) di­methyl­formamide monosolvate monohydrate

aNanning Prefecture Education College, Nanning, Guangxi 530001, People's Republic of China, and bKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
*Correspondence e-mail: xiaoaojianghunn@yahoo.com.cn

(Received 11 March 2012; accepted 28 March 2012; online 18 April 2012)

In the title trinuclear NiII compound, [Ni3(C18H19N2O3)2(C5H5N)4]·C3H7NO·H2O, three NiII cations are bridged by two N′-(adamantan-1-ylcarbon­yl)-2-oxidobenzohydrazidate trianions. The central NiII cation has a distorted octa­hedral N4O2 coordination environment where a reverse torsion occurs between the two bridging ligands, whereas the two NiII cations on the sides each adopt an N2O2 square-planar coordination. Weak intra­molecular C—H⋯O and C—H⋯N inter­actions help to stabilize the mol­ecular structure. In the crystal, the lattice water mol­ecule links with the NiII complex and dimethyl­formamide solvent mol­ecule via O—H⋯O hydrogen bonding.

Related literature

For the use of N-acyl­salicylhydrazide in the construction of polynuclear complexes and metallacrown structures, see: Liu et al. (2008[Liu, W. L., Lee, K., Park, M., Jonh, R. P., Moon, D., Zou, Y., Liu, X. F., Ri, H. C., Kim, G. H. & Lah, M. S. (2008). Inorg. Chem. 47, 8807-8812.]); Moon et al. (2006[Moon, D., Leek, K., John, R. P., Kim, G. H., Suh, B. J. & Lah, M. S. (2006). Inorg. Chem. 45, 7991-8004.]); Qin et al. (2011[Qin, S.-N., Zu, C., Chen, Z.-L., Huang, W.-Y., Qin, J.-K. & Liang, F.-P. (2011). Inorg. Chem. Commun. 11, 1036-1038.]); Wang et al. (2005[Wang, C.-X., Du, C.-X., Li, Y.-H. & Wu, Y.-J. (2005). Inorg. Chem. Commun. 8, 379-381.]). For applications of complexes with N-acyl­salicyl­hydrazide ligands, see: Alexiou et al. (2003[Alexiou, M., Tsivikas, I., Dendrinou-Samara, C., Pantazaki, A. A., Trikalitis, P., Lalioti, N., Kyriakidis, D. A. & Kessissoglou, D. P. (2003). J. Inorg. Biochem. 93, 256-264.]); Li et al. (1996[Li, S.-X., Hu, S.-Z. & Wu, W.-S. (1996). Chin. J. Struct. Chem. 15(2), 134-137.]); Zeng et al. (2007[Zeng, M.-H., Yao, M.-X., Liang, H., Zhang, W.-X. & Chen, X.-M. (2007). Angew. Chem. Int. Ed. 46, 1832-1835.]); Zhou et al. (2010[Zhou, Y.-L., Zeng, M.-H., Wei, L.-Q., Li, B.-W. & Kurmoo, M. (2010). Chem. Mater. 22, 4295-4303.]). For related structures, see: Lin et al. (2007[Lin, S., Yang, M.-X. & Liu, S.-X. (2007). Polyhedron, 26, 4793-4798.]); Meng et al. (2007[Meng, X.-G., Lou, W., Sun, X.-Z., Xiao, F.-P., Shen, J.-F., Zhong, Y., Cheng, G.-Z. & Ji, Z.-P. (2007). Inorg. Chem. Commun. 10, 1351-1353.]); Xiao & Jin (2008[Xiao, F.-P. & Jin, L.-F. (2008). Z. Anorg. Allg. Chem. 34, 397-402.]); Yang & Lin (2005[Yang, M.-X. & Lin, S. (2005). Acta Cryst. E61, m1095-m1096.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni3(C18H19N2O3)2(C5H5N)4]·C3H7NO·H2O

  • Mr = 1206.35

  • Triclinic, [P \overline 1]

  • a = 14.3496 (8) Å

  • b = 14.8499 (9) Å

  • c = 15.2256 (9) Å

  • α = 62.061 (1)°

  • β = 72.261 (1)°

  • γ = 85.202 (1)°

  • V = 2723.3 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.09 mm−1

  • T = 185 K

  • 0.27 × 0.22 × 0.15 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.757, Tmax = 0.853

  • 13829 measured reflections

  • 9496 independent reflections

  • 8034 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.04

  • 9496 reflections

  • 714 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.66 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O8—H8A⋯O7i 0.85 1.97 2.821 (5) 179
O8—H8B⋯O6ii 0.85 2.10 2.952 (4) 179
C2—H2A⋯O5 0.99 2.46 3.356 (4) 151
C3—H3B⋯O5 0.99 2.55 3.425 (3) 147
C24—H24A⋯N7 0.99 2.52 3.382 (4) 145
C31—H31B⋯O2 0.99 2.30 3.259 (4) 163
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2007[Bruker. (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker. (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Metal complexes of hydrazide and its ramification have been paid much attention to in recent years because of their prodigious applications in magnetism material, optical material, automatic recognition and assembly of molecules, catalysis and biochemistry, and so on (Alexiou et al., 2003; Li et al., 1996; Zeng et al., 2007; Zhou et al., 2010). N-acylsalicylhydrazide ligands, one of this type of ligand, which contain N, O coordination atoms, the great conjugated system and rich hydrogen-bonded donors and accepters, have been widely used to construct polynuclear complexes and coordination polymers with interesting structural motifs, such as the one-dimensional, the two-dimensional, the three-dimensional and the metallacrown(Liu et al., 2008; Moon et al., 2006; Qin et al., 2011; Wang et al., 2005). For nickel(II) complexes with N-acylsalicylhydrazide ligands, we can see that trinuclear complexes is more common from the former reports (Lin et al., 2007); Meng et al., 2007); Xiao & Jin, 2008); Yang & Lin, 2005) and most of them are unstable in air. We report here a new trinuclear nickel(II) complex, [Ni3(C18H19N2O3)2(py)4].DMF.H2O, which is stable at room temperature. Its molecular configuration was illustrated in Fig. 1.

In the molecular structure, the arrangement of three Ni2+ ions and the ligands which were coordinated to the central Ni2+ ion in axial positions are different from the reported trinuclear nickel(II) complexes containing N-acylsalicylhydrazide ligands (Yang & Lin, 2005; Xiao & Jin, 2008). In this complex, three Ni2+ ions are arranged in an arcuate shape. The central Ni2 atom adopts a distorted octahedral geometry and is coordinated by two hydrazide nitrogen atoms (N1, N4) and two salicyl carbonyl oxygen atoms (O2, O5) from two bridge deprotonated N-adamantanecarbonylsalicylichydrazide ligands (abbreviated as (ashz)3-) in the equatorial plane and by two nitrogen atoms (N7, N10) from twopyridine molecules in the axial positions. There is a reverse torsion to be occurred between the two planes of the bridge (ashz)3- ligands because of the steric hindrance effect caused by adamantly. This torsion led the bond angles of O5—Ni2—N10 and O2—Ni2—N10 to be pressed to 85.958 (3)° and 84.284 (3)° respectively from the ideal 90°. Two other Ni2+ ions on two side adopt square-planar coordination environments and are coordinated respectively by a phenolic oxygen atom, a adamantanecarbonyl oxygen atom, a hydrazide nitrogen atom and a pyridine nitrogen atom. By O(8)—H(8 A)···O(7) and O(8)—H(8B)···O(6) hydrogen bonds, two hydrogen atoms of water molecule are respectively connected to the phenolic oxygen atom(O6) and the oxygen atom(O7) of DMF to forming dimethylformamide solvate monohydrate.

Related literature top

For the use of N-acylsalicylhydrazide in the construction of polynuclear complexes and metallacrown structures, see: Liu et al. (2008); Moon et al. (2006); Qin et al. (2011); Wang et al. (2005). For applications of complexes with N-acylsalicylhydrazide ligands, see: Alexiou et al. (2003); Li et al. (1996); Zeng et al. (2007); Zhou et al. (2010). For related structures, see: Lin et al. (2007); Meng et al. (2007); Xiao & Jin (2008); Yang & Lin (2005).

Experimental top

Synthesis of ligand H3ashz

Adamantanecarbonyl chloride (6.0 g, 0.03 mol) which was dissolved in tetrahydrofuran(30.0 ml)was dropped slowly into a solution of salicylhydrazide (5.5 g, 0.036 mol) and triethylamine(2.0 ml) dissolved in 60.0 ml of tetrahydrofuran at 0°C. After dropped off, the mixture was slowly warmed up to the room temperature, stirred continually for 24 h and then filtered. The filtrate was recrystallizated by distilled water, and the yellow product was obtained(yield 8.31 g, 87.5%). IR(PE Spectrum One FT—IR Spectrometer, KBr tablet, cm-1): 3352(m), 3243(s), 2915(s), 2851(m), 1665(s), 1637(s), 1608(m), 1531(m), 1515(m), 1495(m), 1456(m). 1278(m), 1236(s), 749(m), 709(m). ESI-Ms: M—H¯ peak at m/z 313.01.

Synthesis of the complex

[Ni3(C18H19N2O3)2(py)4].DMF.H2O Ni(OAc)2.4H2O(0.15 mmol), H3ashz (0.10 mmol) and five drops of pyridine were mixed into the solution of DMF(2 ml) and acetonitrile (10 ml). Stirring for 10 min, the resulting solution was filtered and left to stand at room temperature. Red rhomboid crystals suitable for X-ray analysis were obtained (yield 52.1%) by slowly volatilizing the solvent over a period of two weeks. Carbon, hydrogen and nitrogen were determined by a Perkin-Elmer 2400II CHN element analysis instrument. Analysis, calculated for [Ni3(C18H19N2O3)2(py)4].DMF.H2O: C, 58.74%: H, 5.60%; N, 10.44%. found: C, 58.87%; H, 5.60%; N, 10.53%. IR(KBr tablet, cm-1): 3468(w), 3071(w), 2903(s), 2840(m), 1670(m), 1597(s), 1569(s), 1503(s), 1481(s), 1443(s), 1403(s), 1334(m), 1305(m), 1264(m), 753(s), 693(s).

Refinement top

H atoms were placed in geometrically calculated positions and refined as riding atoms, with O—H = 0.85 and C—H = 0.95–1.00 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,O) for the others.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. H atoms not involved in hydrogen bonds have been omitted for clarity. Symmetry codes: (i) -1+x, y, z; (ii) x, 1-y, -z; (iii) x, y, -1+z.
Bis[µ-N'-(adamantan-1-ylcarbonyl)-2- oxidobenzohydrazidato(3-)]tetrapyridinetrinickel(II) dimethylformamide monosolvate monohydrate top
Crystal data top
[Ni3(C18H19N2O3)2(C5H5N)4]·C3H7NO·H2OZ = 2
Mr = 1206.35F(000) = 1264
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 14.3496 (8) ÅCell parameters from 6088 reflections
b = 14.8499 (9) Åθ = 2.2–26.0°
c = 15.2256 (9) ŵ = 1.09 mm1
α = 62.061 (1)°T = 185 K
β = 72.261 (1)°Block, red
γ = 85.202 (1)°0.27 × 0.22 × 0.15 mm
V = 2723.3 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
9496 independent reflections
Radiation source: fine-focus sealed tube8034 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ϕ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1617
Tmin = 0.757, Tmax = 0.853k = 1717
13829 measured reflectionsl = 1518
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0519P)2 + 1.7341P]
where P = (Fo2 + 2Fc2)/3
9496 reflections(Δ/σ)max < 0.001
714 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Ni3(C18H19N2O3)2(C5H5N)4]·C3H7NO·H2Oγ = 85.202 (1)°
Mr = 1206.35V = 2723.3 (3) Å3
Triclinic, P1Z = 2
a = 14.3496 (8) ÅMo Kα radiation
b = 14.8499 (9) ŵ = 1.09 mm1
c = 15.2256 (9) ÅT = 185 K
α = 62.061 (1)°0.27 × 0.22 × 0.15 mm
β = 72.261 (1)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
9496 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
8034 reflections with I > 2σ(I)
Tmin = 0.757, Tmax = 0.853Rint = 0.016
13829 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.04Δρmax = 0.39 e Å3
9496 reflectionsΔρmin = 0.66 e Å3
714 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.29062 (18)0.3762 (2)0.3952 (2)0.0228 (6)
C20.35980 (19)0.4437 (2)0.2850 (2)0.0258 (6)
H2A0.37040.40780.24240.031*
H2B0.32940.50820.25070.031*
C30.3398 (2)0.2765 (2)0.4466 (2)0.0299 (6)
H3A0.29650.23220.51760.036*
H3B0.35010.23930.40530.036*
C40.4391 (2)0.3006 (3)0.4531 (2)0.0360 (7)
H40.47030.23540.48630.043*
C50.5064 (2)0.3679 (3)0.3430 (2)0.0364 (7)
H5A0.51750.33150.30080.044*
H5B0.57060.38310.34660.044*
C60.4585 (2)0.4677 (2)0.2919 (2)0.0320 (7)
H60.50260.51160.22010.038*
C70.4238 (2)0.3567 (3)0.5181 (3)0.0439 (8)
H7A0.48770.37160.52270.053*
H7B0.38110.31320.58970.053*
C80.3763 (2)0.4563 (3)0.4670 (3)0.0404 (8)
H80.36610.49300.50960.048*
C90.4435 (2)0.5240 (3)0.3569 (3)0.0403 (8)
H9A0.41350.58910.32400.048*
H9B0.50760.53980.36040.048*
C100.2769 (2)0.4329 (2)0.4610 (2)0.0313 (7)
H10A0.24570.49750.42910.038*
H10B0.23310.39010.53230.038*
C110.19072 (18)0.3516 (2)0.39238 (19)0.0216 (5)
C120.04791 (18)0.30740 (19)0.27002 (19)0.0213 (5)
C130.05672 (18)0.28752 (19)0.2881 (2)0.0223 (5)
C140.0812 (2)0.2582 (2)0.2221 (2)0.0279 (6)
H140.03010.25300.16810.033*
C150.1763 (2)0.2367 (2)0.2332 (2)0.0327 (7)
H150.19070.21550.18850.039*
C160.2518 (2)0.2463 (2)0.3109 (2)0.0345 (7)
H160.31810.23330.31820.041*
C170.23028 (19)0.2746 (2)0.3770 (2)0.0307 (6)
H170.28250.28140.42920.037*
C180.13288 (19)0.2938 (2)0.3693 (2)0.0243 (6)
C190.1626 (2)0.2900 (2)0.6377 (2)0.0325 (7)
H190.19030.25180.61500.039*
C200.2156 (2)0.2941 (2)0.7278 (2)0.0362 (7)
H200.27790.25780.76730.043*
C210.1772 (2)0.3516 (2)0.7602 (2)0.0364 (7)
H210.21310.35600.82160.044*
C220.0864 (2)0.4021 (2)0.7018 (2)0.0324 (7)
H220.05900.44330.72150.039*
C230.0353 (2)0.3926 (2)0.6140 (2)0.0279 (6)
H230.02870.42530.57570.033*
C240.2374 (2)0.4137 (2)0.0965 (2)0.0319 (6)
H24A0.22070.42270.03310.038*
H24B0.30190.45070.14300.038*
C250.1590 (2)0.4585 (2)0.1525 (2)0.0350 (7)
H250.15610.53290.17210.042*
C260.0597 (2)0.4028 (2)0.0788 (2)0.0360 (7)
H26A0.00830.43190.11350.043*
H26B0.04290.41170.01540.043*
C270.0641 (2)0.2892 (2)0.0488 (2)0.0336 (7)
H270.00120.25290.00090.040*
C280.0900 (2)0.2746 (3)0.1456 (2)0.0392 (7)
H28A0.03850.30090.18070.047*
H28B0.09370.20100.12570.047*
C290.1886 (2)0.3319 (3)0.2198 (2)0.0392 (8)
H290.20490.32300.28390.047*
C300.2681 (2)0.2875 (3)0.1657 (2)0.0345 (7)
H30A0.33250.32360.21360.041*
H30B0.27220.21430.14760.041*
C310.1426 (2)0.2434 (2)0.0066 (2)0.0289 (6)
H31A0.14500.16980.02600.035*
H31B0.12560.25020.07120.035*
C320.1844 (2)0.4455 (3)0.2508 (2)0.0413 (8)
H32A0.13410.47480.28690.050*
H32B0.24860.48200.29890.050*
C330.32242 (19)0.2535 (2)0.0119 (2)0.0247 (6)
C340.24377 (19)0.2993 (2)0.0659 (2)0.0243 (6)
C350.42577 (18)0.1992 (2)0.1817 (2)0.0222 (5)
C360.50165 (19)0.1339 (2)0.2230 (2)0.0264 (6)
C370.5680 (2)0.0860 (2)0.1709 (2)0.0331 (7)
C380.6336 (2)0.0212 (3)0.2204 (3)0.0467 (9)
H380.67720.01310.18710.056*
C390.6363 (2)0.0061 (3)0.3159 (3)0.0469 (9)
H390.68190.03720.34720.056*
C400.5723 (2)0.0543 (3)0.3662 (3)0.0407 (8)
H400.57380.04450.43200.049*
C410.5066 (2)0.1165 (2)0.3199 (2)0.0309 (6)
H410.46280.14900.35510.037*
C420.6283 (2)0.0585 (2)0.0914 (3)0.0362 (7)
H420.64470.02970.02810.043*
C430.6803 (2)0.0324 (3)0.1681 (3)0.0433 (8)
H430.73170.01240.15780.052*
C440.6563 (2)0.0725 (3)0.2593 (3)0.0464 (9)
H440.69070.05550.31300.056*
C450.5820 (2)0.1375 (3)0.2717 (3)0.0477 (9)
H450.56400.16620.33410.057*
C460.5337 (2)0.1605 (3)0.1918 (3)0.0407 (8)
H460.48220.20540.20090.049*
C470.37565 (19)0.4790 (2)0.0152 (2)0.0283 (6)
H470.42390.43100.01600.034*
C480.3986 (2)0.5787 (2)0.0627 (2)0.0339 (7)
H480.46160.59880.11310.041*
C490.3285 (2)0.6488 (2)0.0661 (2)0.0358 (7)
H490.34200.71780.11920.043*
C500.2380 (2)0.6164 (2)0.0096 (2)0.0330 (7)
H500.18800.66260.00910.040*
C510.2220 (2)0.5157 (2)0.0856 (2)0.0269 (6)
H510.16010.49420.13800.032*
C520.1332 (2)0.0861 (2)0.2905 (2)0.0290 (6)
H520.12200.11830.22430.035*
C530.2090 (2)0.0869 (2)0.4018 (2)0.0327 (7)
H530.25260.11940.41600.039*
C540.1647 (2)0.0083 (2)0.4786 (2)0.0398 (8)
H540.17750.03980.54390.048*
C550.0864 (2)0.0088 (2)0.3630 (2)0.0372 (7)
H550.04410.04080.34690.045*
C590.0459 (3)0.0942 (4)0.8286 (4)0.0659 (11)
H590.06090.16170.78730.079*
C600.0721 (4)0.0299 (4)0.8530 (5)0.115 (2)
H60A0.12050.02170.88270.172*
H60B0.10210.06070.80730.172*
H60C0.01580.07440.90930.172*
C610.1112 (3)0.1364 (4)0.6989 (3)0.0745 (13)
H61A0.08160.20090.66600.112*
H61B0.13130.10630.65150.112*
H61C0.16860.14940.71440.112*
N10.17739 (14)0.33462 (16)0.31992 (16)0.0207 (5)
N20.07407 (14)0.31891 (17)0.34132 (16)0.0209 (5)
N30.07305 (16)0.33827 (18)0.58081 (17)0.0264 (5)
N40.32325 (15)0.25005 (17)0.07580 (17)0.0224 (5)
N50.40790 (15)0.19873 (17)0.10142 (17)0.0238 (5)
N60.55583 (16)0.12256 (19)0.10201 (19)0.0311 (5)
N70.28944 (15)0.44640 (17)0.08939 (16)0.0217 (5)
N80.0404 (2)0.0667 (2)0.7946 (3)0.0532 (8)
C620.1021 (2)0.0562 (2)0.4588 (2)0.0390 (7)
H620.07010.12110.51050.047*
N100.19352 (16)0.13518 (17)0.30863 (17)0.0255 (5)
Ni10.00220 (2)0.32886 (3)0.45606 (3)0.02189 (10)
Ni20.24878 (2)0.29225 (3)0.19742 (2)0.01995 (9)
Ni30.48439 (2)0.15812 (3)0.00729 (3)0.02747 (10)
O10.11573 (13)0.34834 (15)0.46962 (14)0.0266 (4)
O20.11103 (12)0.31102 (14)0.18823 (13)0.0220 (4)
O30.11911 (13)0.31607 (15)0.43894 (14)0.0279 (4)
O40.39292 (14)0.21619 (16)0.06013 (15)0.0320 (5)
O50.37708 (12)0.24968 (14)0.22717 (14)0.0252 (4)
O60.57437 (14)0.09919 (18)0.07684 (17)0.0400 (5)
O70.1092 (2)0.0409 (3)0.9089 (3)0.0913 (11)
O80.2154 (3)0.8318 (3)0.0105 (3)0.1010 (12)
H8B0.27580.85220.01460.121*
H8A0.18390.87050.03450.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0212 (13)0.0271 (14)0.0230 (14)0.0013 (11)0.0071 (11)0.0137 (12)
C20.0239 (14)0.0304 (15)0.0240 (14)0.0002 (12)0.0054 (11)0.0141 (12)
C30.0283 (15)0.0338 (16)0.0276 (15)0.0035 (12)0.0102 (12)0.0134 (13)
C40.0278 (15)0.0461 (19)0.0400 (17)0.0085 (14)0.0185 (14)0.0206 (15)
C50.0231 (14)0.052 (2)0.0422 (18)0.0041 (14)0.0113 (13)0.0275 (16)
C60.0217 (14)0.0419 (18)0.0324 (16)0.0059 (13)0.0032 (12)0.0190 (14)
C70.0322 (17)0.070 (2)0.0373 (18)0.0011 (16)0.0166 (14)0.0273 (18)
C80.0330 (16)0.063 (2)0.0461 (19)0.0016 (15)0.0109 (14)0.0418 (18)
C90.0295 (16)0.050 (2)0.053 (2)0.0046 (14)0.0106 (15)0.0339 (17)
C100.0290 (15)0.0447 (18)0.0298 (15)0.0033 (13)0.0089 (12)0.0251 (14)
C110.0216 (13)0.0208 (13)0.0209 (13)0.0021 (11)0.0063 (11)0.0086 (11)
C120.0233 (13)0.0176 (13)0.0218 (13)0.0041 (10)0.0086 (11)0.0076 (11)
C130.0197 (13)0.0199 (13)0.0242 (14)0.0019 (10)0.0082 (11)0.0069 (11)
C140.0265 (14)0.0333 (16)0.0276 (15)0.0056 (12)0.0108 (12)0.0162 (13)
C150.0301 (15)0.0392 (17)0.0367 (17)0.0019 (13)0.0152 (13)0.0209 (14)
C160.0242 (15)0.0390 (18)0.0428 (18)0.0020 (13)0.0132 (13)0.0192 (15)
C170.0203 (14)0.0358 (17)0.0334 (16)0.0045 (12)0.0054 (12)0.0161 (13)
C180.0237 (13)0.0225 (14)0.0243 (14)0.0039 (11)0.0074 (11)0.0092 (11)
C190.0285 (15)0.0390 (17)0.0290 (15)0.0002 (13)0.0028 (12)0.0182 (14)
C200.0287 (15)0.0429 (18)0.0281 (16)0.0012 (14)0.0008 (12)0.0151 (14)
C210.0401 (17)0.0429 (18)0.0271 (16)0.0132 (15)0.0061 (13)0.0212 (14)
C220.0404 (17)0.0335 (16)0.0318 (16)0.0125 (14)0.0155 (14)0.0209 (14)
C230.0280 (14)0.0295 (15)0.0271 (15)0.0044 (12)0.0099 (12)0.0134 (13)
C240.0346 (16)0.0306 (16)0.0338 (16)0.0027 (13)0.0130 (13)0.0161 (13)
C250.0460 (18)0.0265 (16)0.0359 (17)0.0062 (14)0.0204 (14)0.0130 (13)
C260.0341 (16)0.0458 (19)0.0361 (17)0.0154 (14)0.0194 (14)0.0220 (15)
C270.0298 (15)0.0387 (17)0.0314 (16)0.0002 (13)0.0119 (13)0.0135 (14)
C280.0503 (19)0.0368 (18)0.0417 (18)0.0061 (15)0.0286 (16)0.0187 (15)
C290.0503 (19)0.049 (2)0.0259 (16)0.0110 (16)0.0180 (14)0.0207 (15)
C300.0394 (17)0.0446 (19)0.0255 (15)0.0098 (14)0.0113 (13)0.0212 (14)
C310.0304 (15)0.0310 (16)0.0247 (14)0.0017 (12)0.0098 (12)0.0116 (12)
C320.0472 (19)0.0436 (19)0.0267 (16)0.0047 (15)0.0159 (14)0.0088 (14)
C330.0221 (13)0.0252 (14)0.0263 (14)0.0023 (11)0.0045 (11)0.0135 (12)
C340.0270 (14)0.0288 (15)0.0219 (14)0.0051 (12)0.0085 (11)0.0153 (12)
C350.0189 (13)0.0202 (13)0.0252 (14)0.0000 (10)0.0044 (11)0.0098 (11)
C360.0196 (13)0.0234 (14)0.0349 (16)0.0023 (11)0.0085 (12)0.0126 (12)
C370.0264 (15)0.0354 (17)0.0438 (18)0.0089 (13)0.0142 (13)0.0225 (14)
C380.0337 (17)0.054 (2)0.064 (2)0.0227 (16)0.0216 (17)0.0357 (19)
C390.0396 (18)0.046 (2)0.060 (2)0.0202 (16)0.0303 (17)0.0215 (18)
C400.0344 (17)0.046 (2)0.0403 (18)0.0066 (15)0.0181 (14)0.0152 (15)
C410.0263 (14)0.0329 (16)0.0322 (16)0.0049 (12)0.0104 (12)0.0136 (13)
C420.0305 (16)0.0313 (17)0.0423 (18)0.0044 (13)0.0026 (13)0.0190 (14)
C430.0399 (18)0.0385 (19)0.051 (2)0.0077 (15)0.0027 (16)0.0281 (17)
C440.0412 (19)0.052 (2)0.052 (2)0.0002 (16)0.0056 (16)0.0393 (18)
C450.0409 (19)0.065 (2)0.045 (2)0.0048 (17)0.0049 (16)0.0367 (19)
C460.0296 (16)0.052 (2)0.0433 (19)0.0060 (15)0.0043 (14)0.0289 (17)
C470.0227 (14)0.0369 (17)0.0275 (15)0.0014 (12)0.0081 (12)0.0163 (13)
C480.0263 (15)0.0441 (18)0.0266 (15)0.0067 (13)0.0061 (12)0.0125 (14)
C490.0414 (17)0.0292 (16)0.0310 (16)0.0070 (14)0.0132 (14)0.0068 (13)
C500.0370 (16)0.0272 (16)0.0342 (16)0.0054 (13)0.0110 (13)0.0142 (13)
C510.0300 (15)0.0270 (15)0.0255 (14)0.0031 (12)0.0059 (12)0.0156 (12)
C520.0335 (15)0.0264 (15)0.0276 (15)0.0029 (12)0.0098 (12)0.0127 (12)
C530.0384 (16)0.0301 (16)0.0309 (16)0.0036 (13)0.0137 (13)0.0135 (13)
C540.056 (2)0.0329 (17)0.0248 (16)0.0079 (15)0.0145 (15)0.0082 (13)
C550.0380 (17)0.0290 (16)0.0439 (19)0.0007 (13)0.0125 (14)0.0158 (14)
C590.054 (2)0.069 (3)0.088 (3)0.014 (2)0.023 (2)0.048 (3)
C600.072 (3)0.061 (3)0.136 (5)0.023 (3)0.002 (3)0.006 (3)
C610.080 (3)0.068 (3)0.066 (3)0.001 (2)0.013 (2)0.029 (2)
N10.0151 (10)0.0241 (12)0.0219 (11)0.0009 (9)0.0050 (9)0.0102 (9)
N20.0158 (10)0.0261 (12)0.0202 (11)0.0003 (9)0.0043 (9)0.0109 (9)
N30.0254 (12)0.0298 (13)0.0240 (12)0.0032 (10)0.0053 (10)0.0141 (10)
N40.0203 (11)0.0229 (12)0.0253 (12)0.0070 (9)0.0084 (9)0.0121 (10)
N50.0178 (11)0.0253 (12)0.0294 (12)0.0069 (9)0.0073 (9)0.0144 (10)
N60.0250 (12)0.0323 (14)0.0361 (14)0.0027 (10)0.0028 (10)0.0200 (11)
N70.0230 (11)0.0241 (12)0.0195 (11)0.0016 (9)0.0064 (9)0.0111 (9)
N80.0508 (18)0.0444 (18)0.072 (2)0.0105 (15)0.0221 (16)0.0325 (17)
C620.0445 (18)0.0221 (15)0.0374 (18)0.0008 (13)0.0065 (14)0.0068 (13)
N100.0253 (12)0.0252 (12)0.0243 (12)0.0058 (10)0.0068 (10)0.0114 (10)
Ni10.01830 (17)0.0270 (2)0.02113 (18)0.00131 (14)0.00339 (14)0.01332 (15)
Ni20.01796 (17)0.02193 (18)0.02015 (18)0.00337 (13)0.00538 (13)0.01051 (14)
Ni30.02173 (18)0.0325 (2)0.0326 (2)0.00796 (15)0.00624 (15)0.02078 (17)
O10.0220 (9)0.0373 (11)0.0223 (10)0.0003 (8)0.0033 (8)0.0171 (9)
O20.0203 (9)0.0279 (10)0.0191 (9)0.0030 (8)0.0062 (7)0.0122 (8)
O30.0195 (9)0.0387 (12)0.0287 (10)0.0031 (8)0.0049 (8)0.0199 (9)
O40.0289 (10)0.0426 (12)0.0322 (11)0.0137 (9)0.0097 (9)0.0252 (10)
O50.0221 (9)0.0299 (10)0.0289 (10)0.0070 (8)0.0092 (8)0.0178 (9)
O60.0298 (11)0.0536 (14)0.0497 (14)0.0211 (10)0.0163 (10)0.0348 (12)
O70.0562 (19)0.088 (2)0.124 (3)0.0048 (18)0.004 (2)0.058 (2)
O80.092 (3)0.090 (3)0.104 (3)0.002 (2)0.002 (2)0.048 (2)
Geometric parameters (Å, º) top
C1—C111.526 (3)C32—H32B0.9900
C1—C31.542 (4)C33—O41.306 (3)
C1—C21.544 (4)C33—N41.315 (3)
C1—C101.548 (4)C33—C341.525 (4)
C2—C61.535 (4)C35—O51.278 (3)
C2—H2A0.9900C35—N51.326 (3)
C2—H2B0.9900C35—C361.480 (3)
C3—C41.540 (4)C36—C411.397 (4)
C3—H3A0.9900C36—C371.413 (4)
C3—H3B0.9900C37—O61.326 (4)
C4—C71.528 (4)C37—C381.409 (4)
C4—C51.531 (4)C38—C391.375 (5)
C4—H41.0000C38—H380.9500
C5—C61.532 (4)C39—C401.385 (5)
C5—H5A0.9900C39—H390.9500
C5—H5B0.9900C40—C411.374 (4)
C6—C91.529 (4)C40—H400.9500
C6—H61.0000C41—H410.9500
C7—C81.528 (5)C42—N61.343 (4)
C7—H7A0.9900C42—C431.384 (4)
C7—H7B0.9900C42—H420.9500
C8—C91.533 (5)C43—C441.373 (5)
C8—C101.535 (4)C43—H430.9500
C8—H81.0000C44—C451.374 (5)
C9—H9A0.9900C44—H440.9500
C9—H9B0.9900C45—C461.383 (4)
C10—H10A0.9900C45—H450.9500
C10—H10B0.9900C46—N61.342 (4)
C11—N11.310 (3)C46—H460.9500
C11—O11.314 (3)C47—N71.333 (3)
C12—O21.278 (3)C47—C481.381 (4)
C12—N21.335 (3)C47—H470.9500
C12—C131.471 (3)C48—C491.380 (4)
C13—C141.404 (4)C48—H480.9500
C13—C181.414 (4)C49—C501.385 (4)
C14—C151.369 (4)C49—H490.9500
C14—H140.9500C50—C511.379 (4)
C15—C161.394 (4)C50—H500.9500
C15—H150.9500C51—N71.346 (3)
C16—C171.375 (4)C51—H510.9500
C16—H160.9500C52—N101.341 (4)
C17—C181.408 (4)C52—C551.380 (4)
C17—H170.9500C52—H520.9500
C18—O31.320 (3)C53—N101.338 (4)
C19—N31.346 (4)C53—C541.384 (4)
C19—C201.378 (4)C53—H530.9500
C19—H190.9500C54—C621.370 (5)
C20—C211.382 (4)C54—H540.9500
C20—H200.9500C55—C621.374 (4)
C21—C221.373 (4)C55—H550.9500
C21—H210.9500C59—O71.217 (5)
C22—C231.380 (4)C59—N81.301 (5)
C22—H220.9500C59—H590.9500
C23—N31.350 (3)C60—N81.413 (5)
C23—H230.9500C60—H60A0.9800
C24—C251.537 (4)C60—H60B0.9800
C24—C341.540 (4)C60—H60C0.9800
C24—H24A0.9900C61—N81.445 (5)
C24—H24B0.9900C61—H61A0.9800
C25—C261.526 (4)C61—H61B0.9800
C25—C321.529 (4)C61—H61C0.9800
C25—H251.0000N1—N21.432 (3)
C26—C271.528 (4)N1—Ni22.180 (2)
C26—H26A0.9900N2—Ni11.822 (2)
C26—H26B0.9900N3—Ni11.926 (2)
C27—C281.520 (4)N4—N51.437 (3)
C27—C311.535 (4)N4—Ni22.176 (2)
C27—H271.0000N5—Ni31.834 (2)
C28—C291.526 (5)N6—Ni31.947 (2)
C28—H28A0.9900N7—Ni22.097 (2)
C28—H28B0.9900C62—H620.9500
C29—C321.525 (5)N10—Ni22.174 (2)
C29—C301.535 (4)Ni1—O31.8124 (18)
C29—H291.0000Ni1—O11.8277 (18)
C30—C341.542 (4)Ni2—O52.0099 (17)
C30—H30A0.9900Ni2—O22.0109 (17)
C30—H30B0.9900Ni3—O41.8226 (19)
C31—C341.543 (4)Ni3—O61.825 (2)
C31—H31A0.9900O8—H8B0.8500
C31—H31B0.9900O8—H8A0.8500
C32—H32A0.9900
C11—C1—C3110.0 (2)H32A—C32—H32B108.3
C11—C1—C2111.9 (2)O4—C33—N4120.3 (2)
C3—C1—C2108.5 (2)O4—C33—C34114.5 (2)
C11—C1—C10109.4 (2)N4—C33—C34125.3 (2)
C3—C1—C10108.2 (2)C33—C34—C24111.4 (2)
C2—C1—C10108.7 (2)C33—C34—C30109.7 (2)
C6—C2—C1110.0 (2)C24—C34—C30108.4 (2)
C6—C2—H2A109.7C33—C34—C31110.3 (2)
C1—C2—H2A109.7C24—C34—C31108.6 (2)
C6—C2—H2B109.7C30—C34—C31108.4 (2)
C1—C2—H2B109.7O5—C35—N5122.6 (2)
H2A—C2—H2B108.2O5—C35—C36119.3 (2)
C4—C3—C1110.3 (2)N5—C35—C36118.0 (2)
C4—C3—H3A109.6C41—C36—C37118.1 (2)
C1—C3—H3A109.6C41—C36—C35118.4 (2)
C4—C3—H3B109.6C37—C36—C35123.5 (2)
C1—C3—H3B109.6O6—C37—C38117.0 (3)
H3A—C3—H3B108.1O6—C37—C36124.5 (3)
C7—C4—C5109.4 (3)C38—C37—C36118.5 (3)
C7—C4—C3109.9 (2)C39—C38—C37121.7 (3)
C5—C4—C3109.4 (2)C39—C38—H38119.2
C7—C4—H4109.4C37—C38—H38119.2
C5—C4—H4109.4C38—C39—C40119.8 (3)
C3—C4—H4109.4C38—C39—H39120.1
C4—C5—C6109.4 (2)C40—C39—H39120.1
C4—C5—H5A109.8C41—C40—C39119.3 (3)
C6—C5—H5A109.8C41—C40—H40120.3
C4—C5—H5B109.8C39—C40—H40120.3
C6—C5—H5B109.8C40—C41—C36122.6 (3)
H5A—C5—H5B108.2C40—C41—H41118.7
C9—C6—C5109.2 (2)C36—C41—H41118.7
C9—C6—C2110.3 (2)N6—C42—C43123.3 (3)
C5—C6—C2109.5 (2)N6—C42—H42118.3
C9—C6—H6109.3C43—C42—H42118.3
C5—C6—H6109.3C44—C43—C42118.8 (3)
C2—C6—H6109.3C44—C43—H43120.6
C4—C7—C8109.1 (2)C42—C43—H43120.6
C4—C7—H7A109.9C43—C44—C45119.0 (3)
C8—C7—H7A109.9C43—C44—H44120.5
C4—C7—H7B109.9C45—C44—H44120.5
C8—C7—H7B109.9C44—C45—C46118.9 (3)
H7A—C7—H7B108.3C44—C45—H45120.6
C7—C8—C9109.7 (3)C46—C45—H45120.6
C7—C8—C10109.8 (3)N6—C46—C45123.3 (3)
C9—C8—C10109.6 (2)N6—C46—H46118.3
C7—C8—H8109.3C45—C46—H46118.3
C9—C8—H8109.3N7—C47—C48123.6 (3)
C10—C8—H8109.3N7—C47—H47118.2
C6—C9—C8109.1 (3)C48—C47—H47118.2
C6—C9—H9A109.9C49—C48—C47118.9 (3)
C8—C9—H9A109.9C49—C48—H48120.6
C6—C9—H9B109.9C47—C48—H48120.6
C8—C9—H9B109.9C48—C49—C50118.6 (3)
H9A—C9—H9B108.3C48—C49—H49120.7
C8—C10—C1110.3 (2)C50—C49—H49120.7
C8—C10—H10A109.6C51—C50—C49118.7 (3)
C1—C10—H10A109.6C51—C50—H50120.7
C8—C10—H10B109.6C49—C50—H50120.7
C1—C10—H10B109.6N7—C51—C50123.3 (3)
H10A—C10—H10B108.1N7—C51—H51118.3
N1—C11—O1120.6 (2)C50—C51—H51118.3
N1—C11—C1124.4 (2)N10—C52—C55123.3 (3)
O1—C11—C1115.0 (2)N10—C52—H52118.3
O2—C12—N2122.0 (2)C55—C52—H52118.3
O2—C12—C13119.4 (2)N10—C53—C54123.2 (3)
N2—C12—C13118.6 (2)N10—C53—H53118.4
C14—C13—C18118.7 (2)C54—C53—H53118.4
C14—C13—C12117.6 (2)C62—C54—C53118.9 (3)
C18—C13—C12123.7 (2)C62—C54—H54120.5
C15—C14—C13122.1 (3)C53—C54—H54120.5
C15—C14—H14118.9C62—C55—C52118.9 (3)
C13—C14—H14118.9C62—C55—H55120.6
C14—C15—C16119.2 (3)C52—C55—H55120.6
C14—C15—H15120.4O7—C59—N8125.6 (5)
C16—C15—H15120.4O7—C59—H59117.2
C17—C16—C15120.1 (3)N8—C59—H59117.2
C17—C16—H16120.0N8—C60—H60A109.5
C15—C16—H16120.0N8—C60—H60B109.5
C16—C17—C18121.7 (3)H60A—C60—H60B109.5
C16—C17—H17119.1N8—C60—H60C109.5
C18—C17—H17119.1H60A—C60—H60C109.5
O3—C18—C17117.5 (2)H60B—C60—H60C109.5
O3—C18—C13124.5 (2)N8—C61—H61A109.5
C17—C18—C13118.0 (2)N8—C61—H61B109.5
N3—C19—C20122.1 (3)H61A—C61—H61B109.5
N3—C19—H19118.9N8—C61—H61C109.5
C20—C19—H19118.9H61A—C61—H61C109.5
C19—C20—C21119.5 (3)H61B—C61—H61C109.5
C19—C20—H20120.2C11—N1—N2108.00 (19)
C21—C20—H20120.2C11—N1—Ni2144.34 (17)
C22—C21—C20118.7 (3)N2—N1—Ni2106.17 (14)
C22—C21—H21120.7C12—N2—N1115.3 (2)
C20—C21—H21120.7C12—N2—Ni1129.67 (17)
C21—C22—C23119.3 (3)N1—N2—Ni1114.78 (15)
C21—C22—H22120.3C19—N3—C23118.0 (2)
C23—C22—H22120.3C19—N3—Ni1120.22 (19)
N3—C23—C22122.3 (3)C23—N3—Ni1121.75 (19)
N3—C23—H23118.8C33—N4—N5107.8 (2)
C22—C23—H23118.8C33—N4—Ni2145.27 (17)
C25—C24—C34110.4 (2)N5—N4—Ni2106.93 (14)
C25—C24—H24A109.6C35—N5—N4115.3 (2)
C34—C24—H24A109.6C35—N5—Ni3129.29 (17)
C25—C24—H24B109.6N4—N5—Ni3114.77 (15)
C34—C24—H24B109.6C46—N6—C42116.7 (3)
H24A—C24—H24B108.1C46—N6—Ni3121.03 (19)
C26—C25—C32109.7 (3)C42—N6—Ni3122.3 (2)
C26—C25—C24108.9 (2)C47—N7—C51117.0 (2)
C32—C25—C24110.0 (2)C47—N7—Ni2123.50 (18)
C26—C25—H25109.4C51—N7—Ni2119.06 (18)
C32—C25—H25109.4C59—N8—C60121.8 (4)
C24—C25—H25109.4C59—N8—C61121.4 (4)
C25—C26—C27109.4 (2)C60—N8—C61116.7 (3)
C25—C26—H26A109.8C54—C62—C55118.9 (3)
C27—C26—H26A109.8C54—C62—H62120.6
C25—C26—H26B109.8C55—C62—H62120.6
C27—C26—H26B109.8C53—N10—C52116.8 (2)
H26A—C26—H26B108.2C53—N10—Ni2122.35 (19)
C28—C27—C26110.2 (2)C52—N10—Ni2120.49 (18)
C28—C27—C31108.6 (2)O3—Ni1—N296.43 (8)
C26—C27—C31110.0 (2)O3—Ni1—O1177.27 (9)
C28—C27—H27109.3N2—Ni1—O183.60 (8)
C26—C27—H27109.3O3—Ni1—N388.29 (9)
C31—C27—H27109.3N2—Ni1—N3175.20 (9)
C27—C28—C29109.4 (2)O1—Ni1—N391.73 (9)
C27—C28—H28A109.8O5—Ni2—O2170.13 (8)
C29—C28—H28A109.8O5—Ni2—N799.08 (8)
C27—C28—H28B109.8O2—Ni2—N790.67 (8)
C29—C28—H28B109.8O5—Ni2—N1085.96 (8)
H28A—C28—H28B108.2O2—Ni2—N1084.28 (8)
C28—C29—C32110.5 (3)N7—Ni2—N10174.94 (8)
C28—C29—C30109.0 (3)O5—Ni2—N478.18 (7)
C32—C29—C30109.6 (3)O2—Ni2—N4103.63 (7)
C28—C29—H29109.2N7—Ni2—N489.49 (8)
C32—C29—H29109.2N10—Ni2—N491.97 (8)
C30—C29—H29109.2O5—Ni2—N1100.54 (7)
C29—C30—C34110.1 (2)O2—Ni2—N177.70 (7)
C29—C30—H30A109.6N7—Ni2—N190.38 (8)
C34—C30—H30A109.6N10—Ni2—N188.28 (8)
C29—C30—H30B109.6N4—Ni2—N1178.67 (8)
C34—C30—H30B109.6O4—Ni3—O6179.06 (9)
H30A—C30—H30B108.2O4—Ni3—N583.07 (9)
C27—C31—C34110.0 (2)O6—Ni3—N596.18 (9)
C27—C31—H31A109.7O4—Ni3—N690.55 (9)
C34—C31—H31A109.7O6—Ni3—N690.20 (9)
C27—C31—H31B109.7N5—Ni3—N6173.61 (10)
C34—C31—H31B109.7C11—O1—Ni1112.84 (16)
H31A—C31—H31B108.2C12—O2—Ni2113.97 (15)
C29—C32—C25108.9 (2)C18—O3—Ni1126.21 (16)
C29—C32—H32A109.9C33—O4—Ni3114.06 (17)
C25—C32—H32A109.9C35—O5—Ni2114.09 (15)
C29—C32—H32B109.9C37—O6—Ni3125.48 (17)
C25—C32—H32B109.9H8B—O8—H8A108.4
C11—C1—C2—C6179.1 (2)O4—C33—N4—N51.7 (3)
C3—C1—C2—C659.3 (3)C34—C33—N4—N5178.5 (2)
C10—C1—C2—C658.1 (3)O4—C33—N4—Ni2177.3 (2)
C11—C1—C3—C4178.1 (2)C34—C33—N4—Ni22.5 (5)
C2—C1—C3—C459.1 (3)O5—C35—N5—N46.4 (4)
C10—C1—C3—C458.6 (3)C36—C35—N5—N4170.3 (2)
C1—C3—C4—C760.1 (3)O5—C35—N5—Ni3164.11 (19)
C1—C3—C4—C560.0 (3)C36—C35—N5—Ni319.2 (4)
C7—C4—C5—C660.5 (3)C33—N4—N5—C35172.6 (2)
C3—C4—C5—C660.0 (3)Ni2—N4—N5—C356.8 (3)
C4—C5—C6—C960.5 (3)C33—N4—N5—Ni30.7 (3)
C4—C5—C6—C260.4 (3)Ni2—N4—N5—Ni3178.72 (10)
C1—C2—C6—C959.7 (3)C45—C46—N6—C420.6 (5)
C1—C2—C6—C560.5 (3)C45—C46—N6—Ni3179.9 (3)
C5—C4—C7—C860.2 (3)C43—C42—N6—C461.0 (4)
C3—C4—C7—C859.9 (3)C43—C42—N6—Ni3179.8 (2)
C4—C7—C8—C960.4 (3)C48—C47—N7—C510.9 (4)
C4—C7—C8—C1060.1 (3)C48—C47—N7—Ni2172.9 (2)
C5—C6—C9—C860.3 (3)C50—C51—N7—C470.3 (4)
C2—C6—C9—C860.1 (3)C50—C51—N7—Ni2172.0 (2)
C7—C8—C9—C660.5 (3)O7—C59—N8—C603.6 (7)
C10—C8—C9—C660.1 (3)O7—C59—N8—C61178.9 (4)
C7—C8—C10—C160.3 (3)C53—C54—C62—C550.8 (5)
C9—C8—C10—C160.2 (3)C52—C55—C62—C540.9 (4)
C11—C1—C10—C8178.7 (2)C54—C53—N10—C521.3 (4)
C3—C1—C10—C858.9 (3)C54—C53—N10—Ni2171.8 (2)
C2—C1—C10—C858.7 (3)C55—C52—N10—C531.2 (4)
C3—C1—C11—N184.0 (3)C55—C52—N10—Ni2172.0 (2)
C2—C1—C11—N136.7 (3)C12—N2—Ni1—O30.8 (2)
C10—C1—C11—N1157.3 (2)N1—N2—Ni1—O3174.76 (17)
C3—C1—C11—O196.0 (3)C12—N2—Ni1—O1176.5 (2)
C2—C1—C11—O1143.3 (2)N1—N2—Ni1—O12.50 (17)
C10—C1—C11—O122.7 (3)C12—N2—Ni1—N3170.0 (11)
O2—C12—C13—C149.4 (4)N1—N2—Ni1—N316.0 (13)
N2—C12—C13—C14169.2 (2)C19—N3—Ni1—O330.2 (2)
O2—C12—C13—C18172.4 (2)C23—N3—Ni1—O3149.9 (2)
N2—C12—C13—C189.1 (4)C19—N3—Ni1—N2139.1 (11)
C18—C13—C14—C150.8 (4)C23—N3—Ni1—N240.8 (13)
C12—C13—C14—C15179.2 (3)C19—N3—Ni1—O1152.6 (2)
C13—C14—C15—C161.4 (5)C23—N3—Ni1—O127.3 (2)
C14—C15—C16—C171.6 (5)C47—N7—Ni2—O540.5 (2)
C15—C16—C17—C180.5 (5)C51—N7—Ni2—O5147.63 (19)
C16—C17—C18—O3177.1 (3)C47—N7—Ni2—O2141.0 (2)
C16—C17—C18—C132.7 (4)C51—N7—Ni2—O230.81 (19)
C14—C13—C18—O3176.9 (2)C47—N7—Ni2—N10144.3 (9)
C12—C13—C18—O31.3 (4)C51—N7—Ni2—N1027.6 (10)
C14—C13—C18—C172.8 (4)C47—N7—Ni2—N437.4 (2)
C12—C13—C18—C17178.9 (2)C51—N7—Ni2—N4134.43 (19)
N3—C19—C20—C211.6 (5)C47—N7—Ni2—N1141.3 (2)
C19—C20—C21—C220.8 (4)C51—N7—Ni2—N146.89 (19)
C20—C21—C22—C231.3 (4)C53—N10—Ni2—O547.3 (2)
C21—C22—C23—N32.7 (4)C52—N10—Ni2—O5139.8 (2)
C34—C24—C25—C2660.8 (3)C53—N10—Ni2—O2131.2 (2)
C34—C24—C25—C3259.5 (3)C52—N10—Ni2—O241.68 (19)
C32—C25—C26—C2760.0 (3)C53—N10—Ni2—N7128.0 (9)
C24—C25—C26—C2760.5 (3)C52—N10—Ni2—N744.9 (10)
C25—C26—C27—C2859.4 (3)C53—N10—Ni2—N4125.3 (2)
C25—C26—C27—C3160.4 (3)C52—N10—Ni2—N461.8 (2)
C26—C27—C28—C2958.6 (3)C53—N10—Ni2—N153.4 (2)
C31—C27—C28—C2962.0 (3)C52—N10—Ni2—N1119.5 (2)
C27—C28—C29—C3259.0 (3)C33—N4—Ni2—O5167.6 (3)
C27—C28—C29—C3061.6 (3)N5—N4—Ni2—O511.41 (15)
C28—C29—C30—C3460.1 (3)C33—N4—Ni2—O222.4 (3)
C32—C29—C30—C3461.0 (3)N5—N4—Ni2—O2158.64 (15)
C28—C27—C31—C3461.3 (3)C33—N4—Ni2—N768.2 (3)
C26—C27—C31—C3459.5 (3)N5—N4—Ni2—N7110.80 (16)
C28—C29—C32—C2559.6 (3)C33—N4—Ni2—N10107.0 (3)
C30—C29—C32—C2560.6 (3)N5—N4—Ni2—N1074.04 (16)
C26—C25—C32—C2959.9 (3)C33—N4—Ni2—N1152 (3)
C24—C25—C32—C2959.9 (3)N5—N4—Ni2—N127 (4)
O4—C33—C34—C24119.0 (3)C11—N1—Ni2—O510.3 (3)
N4—C33—C34—C2460.7 (3)N2—N1—Ni2—O5152.61 (14)
O4—C33—C34—C301.0 (3)C11—N1—Ni2—O2179.6 (3)
N4—C33—C34—C30179.3 (3)N2—N1—Ni2—O217.47 (14)
O4—C33—C34—C31120.3 (3)C11—N1—Ni2—N789.0 (3)
N4—C33—C34—C3159.9 (3)N2—N1—Ni2—N7108.08 (15)
C25—C24—C34—C33179.0 (2)C11—N1—Ni2—N1095.9 (3)
C25—C24—C34—C3058.3 (3)N2—N1—Ni2—N1067.05 (15)
C25—C24—C34—C3159.4 (3)C11—N1—Ni2—N45 (4)
C29—C30—C34—C33179.2 (2)N2—N1—Ni2—N4168 (4)
C29—C30—C34—C2459.0 (3)C35—N5—Ni3—O4170.3 (2)
C29—C30—C34—C3158.7 (3)N4—N5—Ni3—O40.24 (17)
C27—C31—C34—C33179.4 (2)C35—N5—Ni3—O610.3 (3)
C27—C31—C34—C2458.3 (3)N4—N5—Ni3—O6179.17 (18)
C27—C31—C34—C3059.3 (3)C35—N5—Ni3—N6166.5 (8)
O5—C35—C36—C4110.3 (4)N4—N5—Ni3—N64.0 (10)
N5—C35—C36—C41166.4 (3)C46—N6—Ni3—O411.1 (2)
O5—C35—C36—C37171.3 (3)C42—N6—Ni3—O4168.1 (2)
N5—C35—C36—C3711.9 (4)C46—N6—Ni3—O6169.5 (2)
C41—C36—C37—O6177.0 (3)C42—N6—Ni3—O611.3 (2)
C35—C36—C37—O64.7 (5)C46—N6—Ni3—N57.4 (10)
C41—C36—C37—C381.8 (4)C42—N6—Ni3—N5171.8 (8)
C35—C36—C37—C38176.6 (3)N1—C11—O1—Ni14.6 (3)
O6—C37—C38—C39176.9 (3)C1—C11—O1—Ni1175.37 (17)
C36—C37—C38—C391.9 (5)O3—Ni1—O1—C1187.1 (16)
C37—C38—C39—C401.0 (6)N2—Ni1—O1—C113.74 (18)
C38—C39—C40—C410.2 (5)N3—Ni1—O1—C11177.38 (18)
C39—C40—C41—C360.3 (5)N2—C12—O2—Ni217.6 (3)
C37—C36—C41—C400.7 (4)C13—C12—O2—Ni2160.86 (18)
C35—C36—C41—C40177.8 (3)O5—Ni2—O2—C1261.6 (5)
N6—C42—C43—C440.9 (5)N7—Ni2—O2—C12109.35 (18)
C42—C43—C44—C450.3 (5)N10—Ni2—O2—C1270.37 (18)
C43—C44—C45—C460.0 (5)N4—Ni2—O2—C12161.02 (17)
C44—C45—C46—N60.1 (5)N1—Ni2—O2—C1219.11 (17)
N7—C47—C48—C491.4 (4)C17—C18—O3—Ni1172.16 (19)
C47—C48—C49—C500.6 (4)C13—C18—O3—Ni17.6 (4)
C48—C49—C50—C510.5 (4)N2—Ni1—O3—C187.2 (2)
C49—C50—C51—N71.0 (4)O1—Ni1—O3—C1897.7 (16)
N10—C53—C54—C620.3 (5)N3—Ni1—O3—C18171.9 (2)
N10—C52—C55—C620.1 (4)N4—C33—O4—Ni32.1 (3)
O1—C11—N1—N22.5 (3)C34—C33—O4—Ni3178.19 (18)
C1—C11—N1—N2177.5 (2)O6—Ni3—O4—C3337 (6)
O1—C11—N1—Ni2160.2 (2)N5—Ni3—O4—C331.17 (19)
C1—C11—N1—Ni219.8 (5)N6—Ni3—O4—C33179.2 (2)
O2—C12—N2—N10.5 (3)N5—C35—O5—Ni217.5 (3)
C13—C12—N2—N1178.0 (2)C36—C35—O5—Ni2159.12 (19)
O2—C12—N2—Ni1173.44 (18)O2—Ni2—O5—C3586.3 (4)
C13—C12—N2—Ni18.0 (4)N7—Ni2—O5—C35102.88 (18)
C11—N1—N2—C12175.6 (2)N10—Ni2—O5—C3577.54 (18)
Ni2—N1—N2—C1214.7 (2)N4—Ni2—O5—C3515.33 (18)
C11—N1—N2—Ni10.8 (2)N1—Ni2—O5—C35165.03 (18)
Ni2—N1—N2—Ni1170.38 (10)C38—C37—O6—Ni3167.5 (2)
C20—C19—N3—C230.3 (4)C36—C37—O6—Ni313.8 (4)
C20—C19—N3—Ni1179.6 (2)O4—Ni3—O6—C3731 (6)
C22—C23—N3—C191.8 (4)N5—Ni3—O6—C376.7 (3)
C22—C23—N3—Ni1178.2 (2)N6—Ni3—O6—C37173.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8A···O7i0.851.972.821 (5)179
O8—H8B···O6ii0.852.102.952 (4)179
C2—H2A···O50.992.463.356 (4)151
C3—H3B···O50.992.553.425 (3)147
C24—H24A···N70.992.523.382 (4)145
C31—H31B···O20.992.303.259 (4)163
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Ni3(C18H19N2O3)2(C5H5N)4]·C3H7NO·H2O
Mr1206.35
Crystal system, space groupTriclinic, P1
Temperature (K)185
a, b, c (Å)14.3496 (8), 14.8499 (9), 15.2256 (9)
α, β, γ (°)62.061 (1), 72.261 (1), 85.202 (1)
V3)2723.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.27 × 0.22 × 0.15
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.757, 0.853
No. of measured, independent and
observed [I > 2σ(I)] reflections
13829, 9496, 8034
Rint0.016
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.100, 1.04
No. of reflections9496
No. of parameters714
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.66

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8A···O7i0.851.972.821 (5)179
O8—H8B···O6ii0.852.102.952 (4)179
C2—H2A···O50.992.463.356 (4)151
C3—H3B···O50.992.553.425 (3)147
C24—H24A···N70.992.523.382 (4)145
C31—H31B···O20.992.303.259 (4)163
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.
 

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 20971029) and the Guangxi Natural Science Foundation of China (No. 2010GXNSFD013018).

References

First citationAlexiou, M., Tsivikas, I., Dendrinou-Samara, C., Pantazaki, A. A., Trikalitis, P., Lalioti, N., Kyriakidis, D. A. & Kessissoglou, D. P. (2003). J. Inorg. Biochem. 93, 256–264.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationBruker. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker. (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, S.-X., Hu, S.-Z. & Wu, W.-S. (1996). Chin. J. Struct. Chem. 15(2), 134–137.  Google Scholar
First citationLin, S., Yang, M.-X. & Liu, S.-X. (2007). Polyhedron, 26, 4793–4798.  Web of Science CSD CrossRef CAS Google Scholar
First citationLiu, W. L., Lee, K., Park, M., Jonh, R. P., Moon, D., Zou, Y., Liu, X. F., Ri, H. C., Kim, G. H. & Lah, M. S. (2008). Inorg. Chem. 47, 8807–8812.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationMeng, X.-G., Lou, W., Sun, X.-Z., Xiao, F.-P., Shen, J.-F., Zhong, Y., Cheng, G.-Z. & Ji, Z.-P. (2007). Inorg. Chem. Commun. 10, 1351–1353.  Google Scholar
First citationMoon, D., Leek, K., John, R. P., Kim, G. H., Suh, B. J. & Lah, M. S. (2006). Inorg. Chem. 45, 7991–8004.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationQin, S.-N., Zu, C., Chen, Z.-L., Huang, W.-Y., Qin, J.-K. & Liang, F.-P. (2011). Inorg. Chem. Commun. 11, 1036–1038.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, C.-X., Du, C.-X., Li, Y.-H. & Wu, Y.-J. (2005). Inorg. Chem. Commun. 8, 379–381.  Web of Science CSD CrossRef CAS Google Scholar
First citationXiao, F.-P. & Jin, L.-F. (2008). Z. Anorg. Allg. Chem. 34, 397–402.  Web of Science CSD CrossRef Google Scholar
First citationYang, M.-X. & Lin, S. (2005). Acta Cryst. E61, m1095–m1096.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZeng, M.-H., Yao, M.-X., Liang, H., Zhang, W.-X. & Chen, X.-M. (2007). Angew. Chem. Int. Ed. 46, 1832–1835.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhou, Y.-L., Zeng, M.-H., Wei, L.-Q., Li, B.-W. & Kurmoo, M. (2010). Chem. Mater. 22, 4295–4303.  Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 5| May 2012| Pages m619-m620
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