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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1521.
Published online 2010 November 6. doi:  10.1107/S1600536810044624
PMCID: PMC3011808

Bis(nitrato-κ2 O,O′)bis­[N-(triphenyl­meth­yl)pyridin-2-amine-κN 1]nickel(II)

Abstract

In the title compound, [Ni(NO3)2(C24H20N2)2], the NiII atom has a distorted pseudo-octa­hedral coordination geometry defined by two chelating nitrate groups and two pyridine N atoms of the monodentate N-(triphenyl­meth­yl)pyridin-2-amine ligands. Intra­molecular N—H(...)O hydrogen bonds help to establish the configuration.

Related literature

For the isostructural dichlorido-cobalt(II), -zinc(II) and -cadmium(II) complexes with bis­{2-[(triphenyl­meth­yl)amino]­pyrid­yl} ligands, see: Fang et al. (2006 [triangle]); Zhang et al. (2007 [triangle]) and Zhang (2008 [triangle]), respectively.

An external file that holds a picture, illustration, etc.
Object name is e-66-m1521-scheme1.jpg

Experimental

Crystal data

  • [Ni(NO3)2(C24H20N2)2]
  • M r = 855.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1521-efi1.jpg
  • a = 10.287 (2) Å
  • b = 23.462 (5) Å
  • c = 17.868 (4) Å
  • β = 105.266 (3)°
  • V = 4160.3 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.53 mm−1
  • T = 293 K
  • 0.53 × 0.52 × 0.47 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.733, T max = 0.791
  • 20535 measured reflections
  • 7279 independent reflections
  • 4928 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.114
  • S = 1.01
  • 7279 reflections
  • 550 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044624/si2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044624/si2301Isup2.hkl

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

supplementary crystallographic information

Comment

The first example of a distorted tetrahedral metalorganic title related complex, dichloridobis{2-[(triphenylmethyl)amino]pyridyl}cobalt(II), was reported by Fang et al. (2006). We continued the study by replacement of cobalt(II) with zinc(II) (Zhang et al., 2007) and cadmium(II) (Zhang, 2008) as the coordination centre. For the title complex we used two nitrato instead of chlorido ligands in order to study the geometric and packing differences for this structure type.

The molecular structure of (I) is shown in Fig.1. In the title compound, the Ni1 atom is distorted pseudo-tetrahedral coordinated by pyridyl atoms N3, N4 and two pairs of nitrato oxygen atoms O1/O2 and O4/O5 (Table 1). The O1—Ni1—O5 and O2—Ni1—O4 angles are observed: 94.26 (9)° and 91.56 (9)°. These two angles are less than the Cl—Co—Cl, Cl—Zn—Cl and Cl—Cd—Cl angles in the literature (121.18 (3)° for Cl-Cd–Cl). The large volume of the two 2-[N-(triphenylmethyl)imino]pyridyl ligands determine the crystal packing of the Ni(II) title complex and related dichlorido-Co(II) (Fang et al., 2006), dichlorido-Zn(II) (Zhang et al., 2007) and dichlorido-Cd(II) (Zhang, 2008) structures. The four compounds crystallize in the monoclinic space group P21/n and exhibit similar unit-cell parameters. Packing motifs of unit cell projections down the a axis are shown in Zhang et al. (2007) and Zhang (2008) for this structure type. Intramolecular N—H···O hydrogen bonds help to establish the conformation of the title complex (Table 2). Similar properties are observed with N—H···Cl hydrogen bonds in the dichlorido complexes.

Experimental

2-[N-(triphenylmethyl)imino]pyridyl ligand (0.03 g, 0.09 mmol) and Ni(NO3) 2(0.025 g, 0.14 mmol) were dissolved in 5 ml and 10 ml of ethanol respectively, then mixed. The mixed solution was stirred about 30 minutes and covered with hexane (10 ml). After two months, blue crystals were obtained.

Refinement

H atoms were positioned geometrically, with N—H=0.86 Å(for NH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
Molecular structure of (I), showing displacement ellipsids at the 30% probability level. H atoms have been omitted.

Crystal data

[Ni(NO3)2(C24H20N2)2]F(000) = 1784
Mr = 855.57Dx = 1.366 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.287 (2) ÅCell parameters from 3946 reflections
b = 23.462 (5) Åθ = 2.2–21.3°
c = 17.868 (4) ŵ = 0.53 mm1
β = 105.266 (3)°T = 293 K
V = 4160.3 (14) Å3Plate, blue
Z = 40.53 × 0.52 × 0.47 mm

Data collection

Bruker SMART APEXII CCD diffractometer7279 independent reflections
Radiation source: fine-focus sealed tube4928 reflections with I > 2σ(I)
graphiteRint = 0.041
CCD scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −11→12
Tmin = 0.733, Tmax = 0.791k = −27→27
20535 measured reflectionsl = −19→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0524P)2 + 0.5431P] where P = (Fo2 + 2Fc2)/3
7279 reflections(Δ/σ)max = 0.001
550 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.30 e Å3

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 (Å2)

xyzUiso*/Ueq
Ni10.68497 (3)0.181447 (15)0.17328 (2)0.04318 (13)
O10.7259 (2)0.21664 (10)0.07075 (13)0.0656 (6)
O20.83125 (19)0.24336 (8)0.18590 (12)0.0556 (5)
O30.8942 (3)0.27540 (12)0.08652 (16)0.0931 (9)
O40.8238 (2)0.11640 (10)0.16253 (14)0.0660 (6)
O50.6099 (2)0.10632 (8)0.12069 (11)0.0545 (5)
O60.7416 (3)0.03988 (11)0.09769 (16)0.0996 (9)
C10.4878 (3)0.27695 (11)0.18500 (15)0.0393 (6)
C20.3571 (3)0.29778 (12)0.17711 (17)0.0475 (7)
H2A0.34410.33160.20120.057*
C30.2494 (3)0.26823 (13)0.13411 (18)0.0530 (8)
H3A0.16260.28190.12890.064*
C40.2688 (3)0.21793 (13)0.09802 (18)0.0571 (8)
H4A0.19640.19790.06690.068*
C50.3968 (3)0.19888 (13)0.10973 (17)0.0526 (8)
H5A0.41020.16490.08600.063*
C60.6152 (3)0.13579 (11)0.32002 (16)0.0404 (6)
C70.6306 (3)0.13566 (13)0.39981 (16)0.0492 (7)
H7A0.56860.11670.42040.059*
C80.7370 (3)0.16348 (14)0.44772 (18)0.0570 (8)
H8A0.74760.16340.50100.068*
C90.8285 (3)0.19170 (14)0.41694 (19)0.0636 (9)
H9A0.90240.21030.44880.076*
C100.8075 (3)0.19145 (13)0.33879 (17)0.0541 (8)
H10A0.86920.21060.31810.065*
C110.6099 (3)0.35901 (11)0.26601 (16)0.0413 (7)
C120.3994 (3)0.07672 (11)0.28363 (15)0.0407 (7)
C130.5717 (3)0.41085 (12)0.21192 (17)0.0453 (7)
C140.5979 (3)0.46533 (13)0.2424 (2)0.0597 (8)
H14A0.63780.46990.29520.072*
C150.5654 (4)0.51291 (15)0.1954 (2)0.0732 (10)
H15A0.58290.54920.21670.088*
C160.5082 (4)0.50679 (18)0.1184 (3)0.0794 (11)
H16A0.48540.53890.08710.095*
C170.4839 (4)0.45370 (18)0.0866 (2)0.0762 (11)
H17A0.44520.44970.03370.091*
C180.5166 (3)0.40572 (14)0.13285 (19)0.0586 (8)
H18A0.50130.36970.11050.070*
C190.5259 (3)0.35298 (12)0.32558 (16)0.0413 (7)
N10.8190 (3)0.24611 (12)0.11230 (18)0.0611 (7)
N20.7279 (3)0.08570 (13)0.12585 (16)0.0633 (7)
N30.5067 (2)0.22612 (9)0.15372 (12)0.0408 (5)
N40.7028 (2)0.16517 (9)0.28896 (13)0.0411 (5)
N50.6013 (2)0.30583 (9)0.22205 (13)0.0428 (6)
H5B0.67650.29120.21930.051*
N60.5169 (2)0.10664 (9)0.26913 (13)0.0425 (6)
H6A0.52360.10540.22220.051*
C200.4470 (3)0.39598 (13)0.34225 (18)0.0525 (8)
H20A0.43660.42980.31420.063*
C210.3834 (3)0.38893 (16)0.4007 (2)0.0714 (10)
H21A0.33130.41840.41210.086*
C220.3957 (3)0.33925 (16)0.4420 (2)0.0686 (10)
H22A0.35250.33500.48130.082*
C230.4724 (3)0.29587 (15)0.42496 (18)0.0589 (8)
H23A0.48110.26190.45260.071*
C240.5366 (3)0.30271 (12)0.36678 (17)0.0484 (7)
H24A0.58790.27300.35520.058*
C250.7599 (3)0.36597 (12)0.31007 (17)0.0451 (7)
C260.8008 (3)0.37622 (16)0.3884 (2)0.0721 (10)
H26A0.73710.37810.41680.087*
C270.9352 (4)0.3837 (2)0.4253 (2)0.1057 (16)
H27A0.96140.39170.47810.127*
C281.0291 (4)0.3796 (2)0.3850 (3)0.1009 (15)
H28A1.12000.38280.41060.121*
C290.9910 (4)0.37064 (17)0.3065 (3)0.0862 (12)
H29A1.05560.36850.27870.103*
C300.8563 (3)0.36475 (13)0.2689 (2)0.0624 (9)
H30A0.83010.35990.21530.075*
C310.3252 (3)0.11809 (12)0.32560 (16)0.0422 (7)
C320.2881 (3)0.10467 (13)0.39223 (18)0.0539 (8)
H32A0.30920.06900.41490.065*
C330.2197 (3)0.14399 (15)0.4256 (2)0.0660 (9)
H33A0.19530.13440.47060.079*
C340.1878 (3)0.19659 (15)0.3933 (2)0.0644 (9)
H34A0.14160.22270.41600.077*
C350.2242 (3)0.21059 (14)0.3277 (2)0.0647 (9)
H35A0.20230.24620.30510.078*
C360.2935 (3)0.17186 (13)0.29476 (19)0.0554 (8)
H36A0.31960.18220.25060.066*
C370.3108 (3)0.06214 (11)0.20148 (16)0.0426 (7)
C380.1758 (3)0.07570 (13)0.17557 (18)0.0530 (8)
H38A0.13250.09300.20910.064*
C390.1050 (3)0.06387 (15)0.1007 (2)0.0650 (9)
H39A0.01380.07280.08420.078*
C400.1669 (4)0.03915 (14)0.0502 (2)0.0655 (9)
H40A0.11930.0328−0.00110.079*
C410.2990 (3)0.02375 (13)0.07534 (19)0.0612 (9)
H41A0.34140.00640.04130.073*
C420.3699 (3)0.03371 (12)0.15082 (17)0.0519 (8)
H42A0.45860.02120.16820.062*
C430.4392 (3)0.02037 (11)0.32687 (16)0.0423 (7)
C440.3388 (3)−0.01635 (13)0.33673 (17)0.0530 (8)
H44A0.2488−0.00650.31650.064*
C450.3707 (4)−0.06708 (14)0.3760 (2)0.0665 (9)
H45A0.3021−0.09060.38290.080*
C460.5015 (4)−0.08334 (15)0.4049 (2)0.0716 (10)
H46A0.5225−0.11730.43210.086*
C470.6017 (4)−0.04883 (15)0.3930 (2)0.0705 (10)
H47A0.6912−0.05990.41140.085*
C480.5707 (3)0.00223 (13)0.35413 (18)0.0562 (8)
H48A0.63990.02490.34610.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0444 (2)0.0463 (2)0.0411 (2)−0.00194 (17)0.01515 (17)−0.00311 (17)
O10.0695 (15)0.0810 (16)0.0498 (14)−0.0109 (13)0.0223 (12)−0.0027 (12)
O20.0553 (13)0.0595 (13)0.0568 (15)−0.0055 (10)0.0233 (11)−0.0067 (11)
O30.098 (2)0.099 (2)0.099 (2)−0.0251 (16)0.0539 (17)0.0166 (16)
O40.0573 (14)0.0686 (15)0.0732 (16)0.0058 (12)0.0190 (12)−0.0129 (13)
O50.0578 (14)0.0532 (13)0.0527 (13)−0.0010 (11)0.0152 (11)−0.0071 (10)
O60.128 (2)0.0669 (17)0.102 (2)0.0222 (16)0.0274 (17)−0.0336 (16)
C10.0405 (16)0.0413 (16)0.0351 (16)−0.0014 (13)0.0085 (13)0.0023 (13)
C20.0410 (18)0.0467 (17)0.0522 (19)0.0032 (14)0.0077 (14)0.0053 (14)
C30.0402 (18)0.059 (2)0.054 (2)0.0035 (15)0.0021 (14)0.0142 (16)
C40.049 (2)0.056 (2)0.054 (2)−0.0098 (16)−0.0073 (15)0.0042 (16)
C50.054 (2)0.0521 (19)0.0468 (19)−0.0041 (15)0.0043 (15)−0.0056 (15)
C60.0386 (16)0.0419 (16)0.0406 (17)0.0023 (13)0.0104 (13)−0.0033 (13)
C70.0486 (18)0.0594 (19)0.0399 (18)−0.0063 (15)0.0124 (14)−0.0010 (15)
C80.057 (2)0.073 (2)0.0378 (18)−0.0028 (17)0.0073 (15)−0.0057 (16)
C90.051 (2)0.086 (3)0.047 (2)−0.0190 (17)0.0004 (15)−0.0067 (17)
C100.0410 (17)0.071 (2)0.049 (2)−0.0131 (15)0.0099 (15)−0.0019 (16)
C110.0383 (16)0.0398 (16)0.0454 (17)−0.0019 (12)0.0101 (13)−0.0033 (13)
C120.0421 (16)0.0418 (16)0.0397 (16)−0.0035 (13)0.0132 (13)−0.0011 (13)
C130.0384 (16)0.0505 (18)0.0488 (19)0.0000 (13)0.0144 (14)0.0034 (15)
C140.070 (2)0.048 (2)0.061 (2)0.0015 (16)0.0172 (17)0.0029 (17)
C150.084 (3)0.050 (2)0.096 (3)0.0018 (18)0.043 (2)0.010 (2)
C160.085 (3)0.068 (3)0.095 (3)0.018 (2)0.042 (2)0.034 (2)
C170.080 (3)0.091 (3)0.057 (2)0.001 (2)0.0185 (19)0.027 (2)
C180.061 (2)0.060 (2)0.057 (2)−0.0063 (16)0.0188 (17)0.0061 (17)
C190.0325 (15)0.0474 (17)0.0432 (17)−0.0051 (13)0.0087 (12)−0.0058 (14)
N10.0648 (19)0.0613 (18)0.066 (2)−0.0014 (15)0.0325 (16)0.0043 (15)
N20.078 (2)0.0576 (19)0.0553 (18)0.0114 (17)0.0187 (16)−0.0052 (15)
N30.0425 (14)0.0441 (14)0.0345 (13)−0.0003 (11)0.0080 (11)−0.0007 (11)
N40.0339 (13)0.0483 (14)0.0403 (14)−0.0022 (10)0.0085 (11)−0.0015 (11)
N50.0343 (13)0.0444 (14)0.0501 (15)0.0017 (10)0.0116 (11)−0.0081 (11)
N60.0426 (13)0.0522 (14)0.0340 (13)−0.0088 (11)0.0125 (11)−0.0026 (11)
C200.0459 (18)0.0470 (18)0.069 (2)−0.0013 (14)0.0224 (16)−0.0036 (15)
C210.058 (2)0.066 (2)0.103 (3)−0.0010 (18)0.044 (2)−0.016 (2)
C220.062 (2)0.084 (3)0.072 (2)−0.017 (2)0.0383 (19)−0.011 (2)
C230.0515 (19)0.069 (2)0.056 (2)−0.0105 (17)0.0125 (16)0.0095 (17)
C240.0420 (17)0.0520 (19)0.0526 (19)0.0002 (14)0.0149 (14)0.0020 (15)
C250.0407 (16)0.0427 (17)0.0506 (19)−0.0059 (13)0.0098 (14)0.0013 (14)
C260.050 (2)0.108 (3)0.053 (2)−0.0233 (19)0.0054 (16)0.004 (2)
C270.065 (3)0.168 (5)0.070 (3)−0.044 (3)−0.007 (2)0.021 (3)
C280.042 (2)0.139 (4)0.107 (4)−0.023 (2)−0.005 (2)0.023 (3)
C290.048 (2)0.101 (3)0.115 (4)−0.017 (2)0.030 (2)−0.011 (3)
C300.0460 (19)0.069 (2)0.075 (2)−0.0109 (16)0.0199 (17)−0.0081 (18)
C310.0402 (16)0.0474 (17)0.0379 (16)−0.0058 (13)0.0084 (13)−0.0039 (14)
C320.0589 (19)0.0527 (19)0.053 (2)0.0003 (15)0.0193 (16)0.0007 (15)
C330.070 (2)0.077 (3)0.059 (2)−0.0062 (19)0.0326 (18)−0.0098 (19)
C340.058 (2)0.061 (2)0.080 (3)−0.0018 (17)0.0297 (19)−0.0191 (19)
C350.066 (2)0.050 (2)0.079 (3)0.0017 (17)0.0206 (19)−0.0037 (18)
C360.064 (2)0.051 (2)0.055 (2)−0.0001 (16)0.0232 (16)−0.0024 (15)
C370.0432 (17)0.0407 (16)0.0442 (17)−0.0090 (13)0.0122 (13)0.0029 (13)
C380.0500 (19)0.0558 (19)0.052 (2)−0.0069 (15)0.0112 (15)−0.0018 (15)
C390.048 (2)0.072 (2)0.065 (2)−0.0051 (17)−0.0020 (17)−0.0020 (19)
C400.073 (3)0.068 (2)0.047 (2)−0.0184 (19)0.0016 (18)−0.0012 (17)
C410.068 (2)0.061 (2)0.057 (2)−0.0164 (18)0.0189 (18)−0.0173 (17)
C420.0513 (19)0.0510 (19)0.052 (2)−0.0061 (15)0.0119 (15)−0.0088 (15)
C430.0446 (18)0.0426 (16)0.0407 (16)−0.0005 (13)0.0128 (13)0.0014 (13)
C440.0511 (19)0.0503 (19)0.057 (2)−0.0014 (15)0.0133 (15)0.0083 (16)
C450.081 (3)0.049 (2)0.073 (2)−0.0089 (18)0.026 (2)0.0060 (18)
C460.088 (3)0.051 (2)0.072 (3)0.010 (2)0.015 (2)0.0142 (18)
C470.067 (2)0.060 (2)0.081 (3)0.0165 (19)0.0123 (19)0.0123 (19)
C480.052 (2)0.055 (2)0.063 (2)−0.0017 (16)0.0175 (16)−0.0007 (16)

Geometric parameters (Å, °)

Ni1—O52.050 (2)N5—H5B0.8600
Ni1—O22.0607 (19)N6—H6A0.8600
Ni1—N32.061 (2)C20—C211.380 (4)
Ni1—N42.062 (2)C20—H20A0.9300
Ni1—O42.133 (2)C21—C221.368 (5)
Ni1—O12.150 (2)C21—H21A0.9300
O1—N11.254 (3)C22—C231.370 (4)
O2—N11.289 (3)C22—H22A0.9300
O3—N11.213 (3)C23—C241.380 (4)
O4—N21.258 (3)C23—H23A0.9300
O5—N21.287 (3)C24—H24A0.9300
O6—N21.211 (3)C25—C261.372 (4)
C1—N31.353 (3)C25—C301.382 (4)
C1—N51.361 (3)C26—C271.377 (5)
C1—C21.403 (3)C26—H26A0.9300
C2—C31.360 (4)C27—C281.353 (6)
C2—H2A0.9300C27—H27A0.9300
C3—C41.384 (4)C28—C291.369 (6)
C3—H3A0.9300C28—H28A0.9300
C4—C51.354 (4)C29—C301.379 (5)
C4—H4A0.9300C29—H29A0.9300
C5—N31.355 (3)C30—H30A0.9300
C5—H5A0.9300C31—C321.379 (4)
C6—N61.354 (3)C31—C361.381 (4)
C6—N41.363 (3)C32—C331.387 (4)
C6—C71.392 (4)C32—H32A0.9300
C7—C81.365 (4)C33—C341.365 (5)
C7—H7A0.9300C33—H33A0.9300
C8—C91.379 (4)C34—C351.362 (5)
C8—H8A0.9300C34—H34A0.9300
C9—C101.356 (4)C35—C361.379 (4)
C9—H9A0.9300C35—H35A0.9300
C10—N41.352 (3)C36—H36A0.9300
C10—H10A0.9300C37—C381.380 (4)
C11—N51.464 (3)C37—C421.387 (4)
C11—C131.539 (4)C38—C391.373 (4)
C11—C191.545 (4)C38—H38A0.9300
C11—C251.545 (4)C39—C401.363 (5)
C12—N61.478 (3)C39—H39A0.9300
C12—C431.532 (4)C40—C411.363 (4)
C12—C311.546 (4)C40—H40A0.9300
C12—C371.549 (4)C41—C421.374 (4)
C13—C181.382 (4)C41—H41A0.9300
C13—C141.388 (4)C42—H42A0.9300
C14—C151.384 (4)C43—C481.379 (4)
C14—H14A0.9300C43—C441.391 (4)
C15—C161.354 (5)C44—C451.377 (4)
C15—H15A0.9300C44—H44A0.9300
C16—C171.364 (5)C45—C461.362 (5)
C16—H16A0.9300C45—H45A0.9300
C17—C181.384 (4)C46—C471.370 (5)
C17—H17A0.9300C46—H46A0.9300
C18—H18A0.9300C47—C481.380 (4)
C19—C201.375 (4)C47—H47A0.9300
C19—C241.379 (4)C48—H48A0.9300
O5—Ni1—O2146.32 (8)C1—N5—C11127.5 (2)
O5—Ni1—N398.53 (9)C1—N5—H5B116.3
O2—Ni1—N3104.58 (8)C11—N5—H5B116.3
O5—Ni1—N4102.92 (8)C6—N6—C12128.5 (2)
O2—Ni1—N498.69 (9)C6—N6—H6A115.7
N3—Ni1—N496.00 (8)C12—N6—H6A115.7
O5—Ni1—O461.58 (8)C19—C20—C21120.0 (3)
O2—Ni1—O491.55 (9)C19—C20—H20A120.0
N3—Ni1—O4159.34 (9)C21—C20—H20A120.0
N4—Ni1—O494.17 (9)C22—C21—C20121.0 (3)
O5—Ni1—O194.26 (9)C22—C21—H21A119.5
O2—Ni1—O161.40 (8)C20—C21—H21A119.5
N3—Ni1—O191.46 (9)C21—C22—C23119.3 (3)
N4—Ni1—O1159.99 (9)C21—C22—H22A120.3
O4—Ni1—O184.95 (9)C23—C22—H22A120.3
N1—O1—Ni189.87 (18)C22—C23—C24119.9 (3)
N1—O2—Ni192.94 (17)C22—C23—H23A120.0
N2—O4—Ni190.24 (17)C24—C23—H23A120.0
N2—O5—Ni193.21 (17)C19—C24—C23120.9 (3)
N3—C1—N5116.2 (2)C19—C24—H24A119.5
N3—C1—C2120.3 (2)C23—C24—H24A119.5
N5—C1—C2123.5 (3)C26—C25—C30118.5 (3)
C3—C2—C1119.7 (3)C26—C25—C11122.4 (3)
C3—C2—H2A120.1C30—C25—C11119.1 (3)
C1—C2—H2A120.1C25—C26—C27120.7 (3)
C2—C3—C4120.2 (3)C25—C26—H26A119.7
C2—C3—H3A119.9C27—C26—H26A119.7
C4—C3—H3A119.9C28—C27—C26120.3 (4)
C5—C4—C3117.6 (3)C28—C27—H27A119.9
C5—C4—H4A121.2C26—C27—H27A119.9
C3—C4—H4A121.2C27—C28—C29120.3 (4)
C4—C5—N3124.3 (3)C27—C28—H28A119.9
C4—C5—H5A117.9C29—C28—H28A119.9
N3—C5—H5A117.9C28—C29—C30119.7 (4)
N6—C6—N4116.0 (2)C28—C29—H29A120.2
N6—C6—C7123.4 (2)C30—C29—H29A120.2
N4—C6—C7120.6 (3)C29—C30—C25120.5 (3)
C8—C7—C6119.8 (3)C29—C30—H30A119.7
C8—C7—H7A120.1C25—C30—H30A119.7
C6—C7—H7A120.1C32—C31—C36117.6 (3)
C7—C8—C9119.9 (3)C32—C31—C12124.0 (3)
C7—C8—H8A120.1C36—C31—C12118.3 (2)
C9—C8—H8A120.1C31—C32—C33120.4 (3)
C10—C9—C8117.9 (3)C31—C32—H32A119.8
C10—C9—H9A121.0C33—C32—H32A119.8
C8—C9—H9A121.0C34—C33—C32120.8 (3)
N4—C10—C9124.3 (3)C34—C33—H33A119.6
N4—C10—H10A117.8C32—C33—H33A119.6
C9—C10—H10A117.8C35—C34—C33119.5 (3)
N5—C11—C13111.5 (2)C35—C34—H34A120.3
N5—C11—C19109.0 (2)C33—C34—H34A120.3
C13—C11—C19114.1 (2)C34—C35—C36119.9 (3)
N5—C11—C25106.0 (2)C34—C35—H35A120.0
C13—C11—C25107.0 (2)C36—C35—H35A120.0
C19—C11—C25108.9 (2)C35—C36—C31121.7 (3)
N6—C12—C43112.1 (2)C35—C36—H36A119.1
N6—C12—C31108.5 (2)C31—C36—H36A119.1
C43—C12—C31113.4 (2)C38—C37—C42117.9 (3)
N6—C12—C37104.1 (2)C38—C37—C12123.8 (3)
C43—C12—C37107.5 (2)C42—C37—C12118.3 (3)
C31—C12—C37110.8 (2)C39—C38—C37120.6 (3)
C18—C13—C14117.8 (3)C39—C38—H38A119.7
C18—C13—C11122.8 (3)C37—C38—H38A119.7
C14—C13—C11119.4 (3)C40—C39—C38120.7 (3)
C15—C14—C13120.9 (3)C40—C39—H39A119.7
C15—C14—H14A119.6C38—C39—H39A119.7
C13—C14—H14A119.6C41—C40—C39119.6 (3)
C16—C15—C14120.2 (4)C41—C40—H40A120.2
C16—C15—H15A119.9C39—C40—H40A120.2
C14—C15—H15A119.9C40—C41—C42120.2 (3)
C15—C16—C17120.2 (4)C40—C41—H41A119.9
C15—C16—H16A119.9C42—C41—H41A119.9
C17—C16—H16A119.9C41—C42—C37120.8 (3)
C16—C17—C18120.4 (4)C41—C42—H42A119.6
C16—C17—H17A119.8C37—C42—H42A119.6
C18—C17—H17A119.8C48—C43—C44117.1 (3)
C13—C18—C17120.6 (3)C48—C43—C12123.5 (2)
C13—C18—H18A119.7C44—C43—C12119.3 (2)
C17—C18—H18A119.7C45—C44—C43120.9 (3)
C20—C19—C24118.7 (3)C45—C44—H44A119.5
C20—C19—C11123.5 (3)C43—C44—H44A119.5
C24—C19—C11117.7 (2)C46—C45—C44121.0 (3)
O3—N1—O1123.5 (3)C46—C45—H45A119.5
O3—N1—O2121.0 (3)C44—C45—H45A119.5
O1—N1—O2115.5 (2)C45—C46—C47118.9 (3)
O6—N2—O4124.3 (3)C45—C46—H46A120.5
O6—N2—O5121.0 (3)C47—C46—H46A120.5
O4—N2—O5114.7 (3)C46—C47—C48120.5 (3)
C1—N3—C5117.8 (2)C46—C47—H47A119.8
C1—N3—Ni1126.62 (18)C48—C47—H47A119.8
C5—N3—Ni1115.33 (19)C43—C48—C47121.4 (3)
C10—N4—C6117.4 (2)C43—C48—H48A119.3
C10—N4—Ni1114.90 (18)C47—C48—H48A119.3
C6—N4—Ni1127.43 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N5—H5B···O20.862.162.994 (3)165
N6—H6A···O50.862.223.048 (3)162

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2301).

References

  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fang, Y., Huang, C.-Y., Zhu, Z.-M., Yu, X.-L. & You, W.-S. (2006). Acta Cryst. E62, m3347–m3348.
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, G.-N. (2008). Acta Cryst. E64, m357. [PMC free article] [PubMed]
  • Zhang, G.-N., Fang, Y., Huang, C.-Y. & You, W.-S. (2007). Acta Cryst. E63, m2247.

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