PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1467.
Published online 2010 October 30. doi:  10.1107/S1600536810042625
PMCID: PMC3008996

μ-Cyanido-1:2κ2 N:C-tricyanido-2κ3 C-(rac-5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-1κ4 N,N′,N′′,N′′′)dinickel(II) N,N-di­methyl­formamide monosolvate hemi­hydrate

Abstract

The two NiII atoms in the title complex, [Ni2(CN)4(C16H36N4)]·C3H7NO·0.5H2O, are bridged by a cyanide ion. The macrocycle folds around one NiII atom, which is five-coordinated in an NiN5 square-pyramidal geometry. The other NiII atom is surrounded by the cyanide ions in an NiN4 square-planar geometry. The dimethyl­formamide solvent mol­ecule is disordered over two positions in a 0.62 (1):0.38 (1) ratio and the water mol­ecule is disordered about a center of inversion. The dinuclear mol­ecule and solvent mol­ecules are linked by N—H(...)O, N–H(...)N and O—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For two related structures, see: Jiang et al. (2005 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1467-scheme1.jpg

Experimental

Crystal data

  • [Ni2(CN)4(C16H36N4)]·C3H7NO·0.5H2O
  • M r = 588.09
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1467-efi1.jpg
  • a = 10.0122 (5) Å
  • b = 10.2109 (5) Å
  • c = 28.3246 (15) Å
  • β = 91.468 (1)°
  • V = 2894.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.33 mm−1
  • T = 173 K
  • 0.40 × 0.35 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.617, T max = 0.825
  • 14236 measured reflections
  • 6181 independent reflections
  • 4435 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.121
  • S = 1.03
  • 6181 reflections
  • 393 parameters
  • 76 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042625/bt5382sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042625/bt5382Isup2.hkl

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

Acknowledgments

We thank the Scientific Research Fund of Hunan Provincial Education Department (10 C0730) and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have previously reported the adducts of 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with nickel salts. The macrocycle in these adducts chelate to the metal atom in a tetradentate manner. With the counterion as a tetracyanidonickellate(II) dianion, a tetranuclear compound was isolated in which the two dianions each bridges two macrocycle-coordinated nickel atoms (Jiang et al., 2005). Another study reported a macrocycle-nickel–tetracyanidonickellate compound, which exists as a chain (Jiang et al., 2007). In dinuclear [Ni2(C16H36N4)].DMF.0.5H2O (Scheme I, Fig. 1) the two metal atoms are linked by only one cyanide bridge. The dinuclear molecule, DMF molecule and lattice water molecules are linked by N–H···O, N–H···N and O–H···O hydrogen bonds into a linear chain motif.

Experimental

A DMF solution (20 ml) of dipotassium tetracyanonickellate dihydrate (0.139 g, 0.5 mmol) was layered with an acetonitrile solution (20 ml) of [Ni(rac-L)](ClO4)2 (0.272 g, 0.5 mmol) (rac-L = 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane) in a glass tube. After about aone month, blue prismatic crystals formed along the walls.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

The amino H atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.86±0.01 Å and Uiso(H) = 1.5Ueq(N).

The water molecule is disordered about a center-of-inversion, and is assigned half occupany. Two H atoms were placed on the O atom, with one of them in a chemically sensible position on the basis of hydrogen bonding and Uiso(H) = 1.5Ueq(O).

The DMF molecule is disordered over two positions in a 62 (1):38 (1) ratio. The carbon–oxygen distances were restrained to 1.25±0.01 Å, the carboncarbonyl–nitrogen distances to 1.35±0.01 Å and the carbon–carbonmethyl distances to 1.45±0.01 Å. The molecule was restrained to lie on a plane. The anisotropic displacement parameters of the disordered atoms were restrained to be nearly isotropic.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius. The disorder is not shown.

Crystal data

[Ni2(CN)4(C16H36N4)]·C3H7NO·0.5H2OF(000) = 1252
Mr = 588.09Dx = 1.349 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5065 reflections
a = 10.0122 (5) Åθ = 2.5–26.8°
b = 10.2109 (5) ŵ = 1.33 mm1
c = 28.3246 (15) ÅT = 173 K
β = 91.468 (1)°Prim, blue
V = 2894.8 (3) Å30.40 × 0.35 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer6181 independent reflections
Radiation source: fine-focus sealed tube4435 reflections with I > 2σ(I)
graphiteRint = 0.035
[var phi] and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→11
Tmin = 0.617, Tmax = 0.825k = −13→12
14236 measured reflectionsl = −30→36

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0666P)2 + 0.7079P] where P = (Fo2 + 2Fc2)/3
6181 reflections(Δ/σ)max = 0.001
393 parametersΔρmax = 0.55 e Å3
76 restraintsΔρmin = −0.39 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Ni10.40876 (4)0.41556 (4)0.163713 (13)0.02095 (12)
Ni20.41778 (4)0.28354 (4)0.332984 (14)0.02452 (13)
O1W0.5942 (8)−0.0422 (7)0.4816 (2)0.076 (2)0.50
H110.54900.02000.47020.115*0.50
H120.5602−0.06570.50710.115*0.50
N10.2327 (3)0.3662 (3)0.12200 (10)0.0284 (6)
H10.177 (3)0.429 (3)0.1287 (12)0.034*
N20.4790 (3)0.4921 (3)0.09926 (10)0.0282 (6)
H20.532 (3)0.433 (3)0.0872 (11)0.034*
N30.6097 (3)0.4408 (3)0.19194 (9)0.0261 (6)
H30.599 (3)0.435 (3)0.2224 (4)0.031*
N40.4697 (3)0.2182 (3)0.15349 (11)0.0285 (6)
H40.491 (4)0.213 (4)0.1236 (5)0.034*
N50.3642 (3)0.3681 (3)0.23283 (10)0.0310 (6)
N60.1889 (3)0.0938 (3)0.32576 (10)0.0289 (6)
N70.4806 (4)0.1648 (5)0.42804 (14)0.0729 (13)
N80.6614 (4)0.4584 (4)0.33648 (15)0.0586 (10)
C10.2720 (4)0.3856 (4)0.07273 (12)0.0358 (8)
H1A0.19110.39510.05220.043*
H1B0.32210.30800.06190.043*
C20.3578 (3)0.5057 (4)0.06859 (12)0.0335 (8)
H2A0.38390.51740.03540.040*
H2B0.30670.58400.07810.040*
C30.5572 (4)0.6160 (4)0.10311 (13)0.0360 (8)
H3A0.50260.68220.12010.043*
C40.5928 (5)0.6725 (5)0.05472 (15)0.0663 (15)
H4A0.51060.69100.03640.100*
H4B0.64680.60890.03770.100*
H4C0.64370.75380.05920.100*
C50.6883 (4)0.5960 (4)0.13084 (12)0.0341 (8)
H5A0.74220.67650.12730.041*
H5B0.73730.52420.11540.041*
C60.6846 (3)0.5644 (3)0.18365 (12)0.0288 (7)
C70.6187 (4)0.6735 (3)0.21114 (13)0.0370 (8)
H7A0.52500.68170.20070.056*
H7B0.66530.75620.20550.056*
H7C0.62340.65300.24490.056*
C80.8294 (4)0.5519 (4)0.20212 (14)0.0418 (9)
H8A0.83020.51660.23430.063*
H8B0.87180.63840.20230.063*
H8C0.87850.49280.18160.063*
C90.6805 (3)0.3219 (3)0.17783 (14)0.0347 (8)
H9A0.76280.31160.19760.042*
H9B0.70680.32980.14450.042*
C100.5924 (4)0.2031 (3)0.18337 (14)0.0366 (9)
H10A0.64130.12340.17390.044*
H10B0.56820.19330.21690.044*
C110.3705 (4)0.1138 (3)0.16224 (14)0.0356 (8)
H11A0.33660.12570.19490.043*
C120.4307 (4)−0.0238 (4)0.15890 (18)0.0563 (12)
H12A0.5060−0.03190.18150.084*
H12B0.4622−0.03850.12680.084*
H12C0.3625−0.08910.16620.084*
C130.2526 (4)0.1236 (3)0.12764 (13)0.0359 (8)
H13A0.19850.04310.13110.043*
H13B0.28840.12240.09540.043*
C140.1569 (3)0.2413 (3)0.13060 (13)0.0322 (8)
C150.0965 (4)0.2505 (4)0.17929 (14)0.0407 (9)
H15A0.03480.32490.18010.061*
H15B0.16790.26290.20320.061*
H15C0.04790.16950.18600.061*
C160.0434 (4)0.2243 (4)0.09397 (15)0.0504 (11)
H16A−0.00980.30480.09220.076*
H16B−0.01370.15110.10320.076*
H16C0.08090.20600.06300.076*
C170.3803 (3)0.3420 (3)0.27219 (12)0.0266 (7)
C180.2738 (3)0.1684 (3)0.32772 (11)0.0253 (7)
C190.4574 (4)0.2135 (4)0.39238 (14)0.0441 (10)
C200.5677 (4)0.3942 (4)0.33603 (13)0.0354 (8)
O10.5992 (7)0.2131 (7)0.0620 (3)0.064 (2)0.620 (6)
N90.7506 (6)0.0709 (6)0.0306 (2)0.063 (2)0.620 (6)
C210.6732 (6)0.1167 (7)0.0637 (2)0.058 (2)0.620 (6)
H210.67460.06930.09260.070*0.620 (6)
C220.7521 (12)0.1403 (11)−0.0141 (3)0.100 (4)0.620 (6)
H22A0.67440.1984−0.01660.150*0.620 (6)
H22B0.74890.0770−0.04010.150*0.620 (6)
H22C0.83410.1923−0.01570.150*0.620 (6)
C230.8352 (7)−0.0424 (7)0.0360 (3)0.064 (2)0.620 (6)
H23A0.8188−0.08430.06640.095*0.620 (6)
H23B0.9290−0.01560.03480.095*0.620 (6)
H23C0.8152−0.10460.01040.095*0.620 (6)
O1'0.5863 (12)0.2654 (13)0.0530 (4)0.063 (4)0.380 (6)
N9'0.7086 (10)0.1118 (10)0.0163 (2)0.053 (3)0.380 (6)
C21'0.6906 (10)0.2298 (11)0.0351 (3)0.044 (3)0.380 (6)
H21B0.76280.29020.03460.053*0.380 (6)
C22'0.6064 (16)0.0150 (16)0.0151 (7)0.120 (7)0.380 (6)
H22D0.51890.05780.01260.180*0.380 (6)
H22E0.6118−0.03710.04420.180*0.380 (6)
H22F0.6182−0.0423−0.01220.180*0.380 (6)
C23'0.8349 (13)0.0747 (18)−0.0046 (5)0.095 (6)0.380 (6)
H23D0.90480.13660.00550.142*0.380 (6)
H23E0.82500.0763−0.03910.142*0.380 (6)
H23F0.8598−0.01380.00580.142*0.380 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0237 (2)0.0160 (2)0.0233 (2)0.00309 (15)0.00128 (15)0.00060 (16)
Ni20.0249 (2)0.0212 (2)0.0276 (2)−0.00409 (16)0.00209 (17)0.00290 (17)
O1W0.118 (6)0.062 (4)0.048 (4)0.007 (4)−0.008 (4)0.012 (3)
N10.0267 (15)0.0263 (15)0.0323 (15)0.0035 (11)−0.0017 (12)−0.0028 (12)
N20.0302 (16)0.0263 (15)0.0281 (15)0.0010 (12)0.0012 (12)0.0024 (12)
N30.0300 (15)0.0219 (14)0.0262 (14)0.0001 (11)−0.0007 (12)0.0023 (12)
N40.0296 (15)0.0164 (14)0.0395 (16)0.0021 (11)0.0032 (13)0.0003 (12)
N50.0344 (16)0.0250 (15)0.0338 (17)−0.0053 (12)0.0064 (13)0.0025 (13)
N60.0306 (16)0.0225 (15)0.0336 (16)−0.0002 (12)0.0029 (12)0.0012 (12)
N70.054 (3)0.112 (4)0.053 (2)−0.006 (2)−0.0085 (19)0.040 (3)
N80.041 (2)0.044 (2)0.091 (3)−0.0159 (17)0.0035 (19)0.000 (2)
C10.040 (2)0.040 (2)0.0273 (18)−0.0005 (16)−0.0068 (15)−0.0015 (16)
C20.038 (2)0.040 (2)0.0219 (17)0.0006 (16)−0.0022 (15)0.0066 (15)
C30.042 (2)0.031 (2)0.0351 (19)−0.0068 (16)0.0025 (16)0.0113 (16)
C40.074 (3)0.078 (4)0.046 (3)−0.032 (3)−0.007 (2)0.031 (3)
C50.036 (2)0.0317 (19)0.0353 (19)−0.0061 (15)0.0055 (15)0.0002 (16)
C60.0314 (19)0.0251 (18)0.0297 (18)−0.0053 (14)−0.0007 (14)0.0002 (14)
C70.041 (2)0.0260 (18)0.044 (2)−0.0066 (16)0.0026 (17)−0.0060 (16)
C80.036 (2)0.041 (2)0.048 (2)−0.0102 (17)−0.0057 (17)−0.0059 (18)
C90.0248 (18)0.0279 (19)0.051 (2)0.0058 (14)−0.0082 (16)−0.0004 (16)
C100.038 (2)0.0198 (18)0.052 (2)0.0080 (14)−0.0071 (17)0.0012 (16)
C110.035 (2)0.0197 (17)0.052 (2)0.0012 (14)0.0032 (17)−0.0002 (16)
C120.050 (3)0.0140 (19)0.105 (4)0.0030 (17)0.004 (2)0.003 (2)
C130.035 (2)0.0240 (18)0.049 (2)−0.0072 (15)0.0056 (17)−0.0084 (16)
C140.0290 (19)0.0250 (18)0.042 (2)−0.0057 (14)0.0011 (15)−0.0026 (15)
C150.0267 (19)0.042 (2)0.054 (2)−0.0040 (16)0.0095 (17)−0.0040 (18)
C160.037 (2)0.054 (3)0.060 (3)−0.0094 (19)−0.0093 (19)−0.009 (2)
C170.0288 (18)0.0190 (16)0.0322 (19)−0.0051 (13)0.0041 (14)0.0025 (14)
C180.0289 (18)0.0194 (16)0.0277 (17)−0.0032 (14)0.0011 (14)0.0053 (13)
C190.031 (2)0.060 (3)0.042 (2)−0.0073 (18)−0.0011 (17)0.015 (2)
C200.034 (2)0.0273 (19)0.045 (2)−0.0002 (15)0.0024 (16)0.0038 (16)
O10.060 (4)0.084 (6)0.049 (4)0.033 (4)0.013 (3)−0.003 (4)
N90.060 (5)0.079 (5)0.050 (4)0.013 (4)0.011 (3)−0.003 (4)
C210.057 (4)0.080 (5)0.038 (4)0.008 (4)0.008 (3)−0.007 (4)
C220.123 (7)0.097 (7)0.080 (6)0.030 (6)0.010 (6)0.015 (5)
C230.054 (4)0.074 (5)0.064 (5)−0.004 (4)0.023 (4)−0.015 (4)
O1'0.068 (6)0.065 (7)0.057 (6)0.032 (5)0.002 (5)−0.017 (5)
N9'0.052 (6)0.053 (6)0.056 (7)0.000 (5)0.018 (5)−0.023 (5)
C21'0.047 (6)0.047 (6)0.037 (5)0.005 (5)−0.002 (4)−0.004 (5)
C22'0.113 (10)0.091 (9)0.156 (11)−0.002 (8)0.022 (8)−0.014 (8)
C23'0.084 (8)0.105 (9)0.095 (9)0.017 (7)0.008 (7)−0.036 (8)

Geometric parameters (Å, °)

Ni1—N52.076 (3)C8—H8A0.9800
Ni1—N6i2.091 (3)C8—H8B0.9800
Ni1—N22.122 (3)C8—H8C0.9800
Ni1—N42.127 (3)C9—C101.510 (5)
Ni1—N12.156 (3)C9—H9A0.9900
Ni1—N32.161 (3)C9—H9B0.9900
Ni2—C171.852 (3)C10—H10A0.9900
Ni2—C191.861 (4)C10—H10B0.9900
Ni2—C181.863 (3)C11—C131.519 (5)
Ni2—C201.879 (4)C11—C121.533 (5)
O1W—H110.84C11—H11A1.0000
O1W—H120.84C12—H12A0.9800
N1—C11.473 (4)C12—H12B0.9800
N1—C141.507 (4)C12—H12C0.9800
N1—H10.88 (3)C13—C141.540 (5)
N2—C21.481 (4)C13—H13A0.9900
N2—C31.490 (4)C13—H13B0.9900
N2—H20.88 (3)C14—C151.523 (5)
N3—C91.467 (4)C14—C161.529 (5)
N3—C61.489 (4)C15—H15A0.9800
N3—H30.87 (3)C15—H15B0.9800
N4—C101.482 (4)C15—H15C0.9800
N4—C111.483 (4)C16—H16A0.9800
N4—H40.88 (3)C16—H16B0.9800
N5—C171.154 (4)C16—H16C0.9800
N6—C181.142 (4)O1—C211.233 (7)
N6—Ni1ii2.091 (3)N9—C211.318 (7)
N7—C191.144 (5)N9—C231.440 (7)
N8—C201.144 (5)N9—C221.450 (8)
C1—C21.504 (5)C21—H210.9500
C1—H1A0.9900C22—H22A0.9800
C1—H1B0.9900C22—H22B0.9800
C2—H2A0.9900C22—H22C0.9800
C2—H2B0.9900C23—H23A0.9800
C3—C51.526 (5)C23—H23B0.9800
C3—C41.537 (5)C23—H23C0.9800
C3—H3A1.0000O1'—C21'1.228 (9)
C4—H4A0.9800N9'—C21'1.331 (14)
C4—H4B0.9800N9'—C22'1.422 (9)
C4—H4C0.9800N9'—C23'1.461 (9)
C5—C61.532 (5)C21'—H21B0.9500
C5—H5A0.9900C22'—H22D0.9800
C5—H5B0.9900C22'—H22E0.9800
C6—C71.519 (5)C22'—H22F0.9800
C6—C81.534 (5)C23'—H23D0.9800
C7—H7A0.9800C23'—H23E0.9800
C7—H7B0.9800C23'—H23F0.9800
C7—H7C0.9800
N5—Ni1—N6i87.47 (11)H7A—C7—H7B109.5
N5—Ni1—N2168.80 (11)C6—C7—H7C109.5
N6i—Ni1—N288.20 (11)H7A—C7—H7C109.5
N5—Ni1—N488.68 (11)H7B—C7—H7C109.5
N6i—Ni1—N4168.73 (11)C6—C8—H8A109.5
N2—Ni1—N497.42 (11)C6—C8—H8B109.5
N5—Ni1—N1105.64 (11)H8A—C8—H8B109.5
N6i—Ni1—N184.45 (11)C6—C8—H8C109.5
N2—Ni1—N184.20 (11)H8A—C8—H8C109.5
N4—Ni1—N186.41 (11)H8B—C8—H8C109.5
N5—Ni1—N384.24 (11)N3—C9—C10110.4 (3)
N6i—Ni1—N3106.11 (11)N3—C9—H9A109.6
N2—Ni1—N387.05 (11)C10—C9—H9A109.6
N4—Ni1—N384.01 (11)N3—C9—H9B109.6
N1—Ni1—N3166.08 (10)C10—C9—H9B109.6
C17—Ni2—C19176.11 (17)H9A—C9—H9B108.1
C17—Ni2—C1889.49 (14)N4—C10—C9109.5 (3)
C19—Ni2—C1888.66 (15)N4—C10—H10A109.8
C17—Ni2—C2089.51 (15)C9—C10—H10A109.8
C19—Ni2—C2092.17 (16)N4—C10—H10B109.8
C18—Ni2—C20177.02 (15)C9—C10—H10B109.8
H11—O1W—H12108.8H10A—C10—H10B108.2
C1—N1—C14114.5 (3)N4—C11—C13111.0 (3)
C1—N1—Ni1104.7 (2)N4—C11—C12112.5 (3)
C14—N1—Ni1121.1 (2)C13—C11—C12108.7 (3)
C1—N1—H1107 (2)N4—C11—H11A108.2
C14—N1—H1105 (2)C13—C11—H11A108.2
Ni1—N1—H1103 (2)C12—C11—H11A108.2
C2—N2—C3112.6 (3)C11—C12—H12A109.5
C2—N2—Ni1104.8 (2)C11—C12—H12B109.5
C3—N2—Ni1115.8 (2)H12A—C12—H12B109.5
C2—N2—H2109 (2)C11—C12—H12C109.5
C3—N2—H2107 (2)H12A—C12—H12C109.5
Ni1—N2—H2107 (2)H12B—C12—H12C109.5
C9—N3—C6114.2 (3)C11—C13—C14119.4 (3)
C9—N3—Ni1104.6 (2)C11—C13—H13A107.5
C6—N3—Ni1120.7 (2)C14—C13—H13A107.5
C9—N3—H3106 (2)C11—C13—H13B107.5
C6—N3—H3107 (2)C14—C13—H13B107.5
Ni1—N3—H3103 (2)H13A—C13—H13B107.0
C10—N4—C11112.3 (3)N1—C14—C15107.9 (3)
C10—N4—Ni1104.9 (2)N1—C14—C16110.8 (3)
C11—N4—Ni1117.6 (2)C15—C14—C16108.4 (3)
C10—N4—H4109 (2)N1—C14—C13109.6 (3)
C11—N4—H4107 (2)C15—C14—C13111.1 (3)
Ni1—N4—H4105 (2)C16—C14—C13109.1 (3)
C17—N5—Ni1159.5 (3)C14—C15—H15A109.5
C18—N6—Ni1ii157.5 (3)C14—C15—H15B109.5
N1—C1—C2110.5 (3)H15A—C15—H15B109.5
N1—C1—H1A109.5C14—C15—H15C109.5
C2—C1—H1A109.5H15A—C15—H15C109.5
N1—C1—H1B109.5H15B—C15—H15C109.5
C2—C1—H1B109.5C14—C16—H16A109.5
H1A—C1—H1B108.1C14—C16—H16B109.5
N2—C2—C1109.8 (3)H16A—C16—H16B109.5
N2—C2—H2A109.7C14—C16—H16C109.5
C1—C2—H2A109.7H16A—C16—H16C109.5
N2—C2—H2B109.7H16B—C16—H16C109.5
C1—C2—H2B109.7N5—C17—Ni2173.3 (3)
H2A—C2—H2B108.2N6—C18—Ni2176.8 (3)
N2—C3—C5111.6 (3)N7—C19—Ni2176.8 (4)
N2—C3—C4112.8 (3)N8—C20—Ni2177.1 (4)
C5—C3—C4107.0 (3)C21—N9—C23124.4 (7)
N2—C3—H3A108.5C21—N9—C22117.8 (7)
C5—C3—H3A108.5C23—N9—C22117.8 (7)
C4—C3—H3A108.5O1—C21—N9128.3 (7)
C3—C4—H4A109.5O1—C21—H21115.8
C3—C4—H4B109.5N9—C21—H21115.8
H4A—C4—H4B109.5C21'—N9'—C22'122.3 (11)
C3—C4—H4C109.5C21'—N9'—C23'121.6 (11)
H4A—C4—H4C109.5C22'—N9'—C23'116.1 (13)
H4B—C4—H4C109.5O1'—C21'—N9'123.9 (12)
C3—C5—C6119.3 (3)O1'—C21'—H21B118.0
C3—C5—H5A107.5N9'—C21'—H21B118.0
C6—C5—H5A107.5N9'—C22'—H22D109.5
C3—C5—H5B107.5N9'—C22'—H22E109.5
C6—C5—H5B107.5H22D—C22'—H22E109.5
H5A—C5—H5B107.0N9'—C22'—H22F109.5
N3—C6—C7108.3 (3)H22D—C22'—H22F109.5
N3—C6—C5110.9 (3)H22E—C22'—H22F109.5
C7—C6—C5111.6 (3)N9'—C23'—H23D109.5
N3—C6—C8110.6 (3)N9'—C23'—H23E109.5
C7—C6—C8107.8 (3)H23D—C23'—H23E109.5
C5—C6—C8107.7 (3)N9'—C23'—H23F109.5
C6—C7—H7A109.5H23D—C23'—H23F109.5
C6—C7—H7B109.5H23E—C23'—H23F109.5
N5—Ni1—N1—C1−173.4 (2)C14—N1—C1—C2−174.7 (3)
N6i—Ni1—N1—C1100.8 (2)Ni1—N1—C1—C2−39.7 (3)
N2—Ni1—N1—C112.0 (2)C3—N2—C2—C1−170.5 (3)
N4—Ni1—N1—C1−85.8 (2)Ni1—N2—C2—C1−43.8 (3)
N3—Ni1—N1—C1−39.3 (5)N1—C1—C2—N259.1 (4)
N5—Ni1—N1—C14−42.2 (3)C2—N2—C3—C5−174.4 (3)
N6i—Ni1—N1—C14−128.0 (2)Ni1—N2—C3—C565.1 (3)
N2—Ni1—N1—C14143.3 (2)C2—N2—C3—C4−53.9 (4)
N4—Ni1—N1—C1445.4 (2)Ni1—N2—C3—C4−174.4 (3)
N3—Ni1—N1—C1492.0 (5)N2—C3—C5—C6−67.3 (4)
N5—Ni1—N2—C2−134.8 (5)C4—C3—C5—C6168.9 (3)
N6i—Ni1—N2—C2−67.6 (2)C9—N3—C6—C7−165.2 (3)
N4—Ni1—N2—C2102.6 (2)Ni1—N3—C6—C768.8 (3)
N1—Ni1—N2—C217.0 (2)C9—N3—C6—C572.1 (4)
N3—Ni1—N2—C2−173.8 (2)Ni1—N3—C6—C5−53.9 (3)
N5—Ni1—N2—C3−10.2 (7)C9—N3—C6—C8−47.3 (4)
N6i—Ni1—N2—C357.1 (2)Ni1—N3—C6—C8−173.4 (2)
N4—Ni1—N2—C3−132.7 (2)C3—C5—C6—N359.8 (4)
N1—Ni1—N2—C3141.7 (2)C3—C5—C6—C7−61.0 (4)
N3—Ni1—N2—C3−49.1 (2)C3—C5—C6—C8−179.1 (3)
N5—Ni1—N3—C9102.4 (2)C6—N3—C9—C10−174.9 (3)
N6i—Ni1—N3—C9−171.9 (2)Ni1—N3—C9—C10−40.9 (3)
N2—Ni1—N3—C9−84.7 (2)C11—N4—C10—C9−172.1 (3)
N4—Ni1—N3—C913.1 (2)Ni1—N4—C10—C9−43.3 (3)
N1—Ni1—N3—C9−33.6 (5)N3—C9—C10—N459.6 (4)
N5—Ni1—N3—C6−127.3 (2)C10—N4—C11—C13−174.0 (3)
N6i—Ni1—N3—C6−41.6 (2)Ni1—N4—C11—C1364.1 (3)
N2—Ni1—N3—C645.6 (2)C10—N4—C11—C12−52.0 (4)
N4—Ni1—N3—C6143.4 (2)Ni1—N4—C11—C12−173.8 (3)
N1—Ni1—N3—C696.7 (5)N4—C11—C13—C14−67.8 (4)
N5—Ni1—N4—C10−68.0 (2)C12—C11—C13—C14168.0 (3)
N6i—Ni1—N4—C10−138.0 (5)C1—N1—C14—C15−167.1 (3)
N2—Ni1—N4—C10102.6 (2)Ni1—N1—C14—C1566.0 (3)
N1—Ni1—N4—C10−173.8 (2)C1—N1—C14—C16−48.6 (4)
N3—Ni1—N4—C1016.3 (2)Ni1—N1—C14—C16−175.5 (2)
N5—Ni1—N4—C1157.5 (3)C1—N1—C14—C1371.8 (4)
N6i—Ni1—N4—C11−12.5 (7)Ni1—N1—C14—C13−55.1 (3)
N2—Ni1—N4—C11−131.9 (3)C11—C13—C14—N161.6 (4)
N1—Ni1—N4—C11−48.2 (3)C11—C13—C14—C15−57.6 (4)
N3—Ni1—N4—C11141.9 (3)C11—C13—C14—C16−177.0 (3)
N6i—Ni1—N5—C17−117.1 (8)C23—N9—C21—O1179.4 (4)
N2—Ni1—N5—C17−49.8 (11)C22—N9—C21—O10.2 (4)
N4—Ni1—N5—C1773.5 (8)C22'—N9'—C21'—O1'0.4 (4)
N1—Ni1—N5—C17159.3 (8)C23'—N9'—C21'—O1'180.0 (3)
N3—Ni1—N5—C17−10.7 (8)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H11···N70.842.012.825 (8)163
N1—H1···N6i0.88 (3)2.49 (3)2.854 (4)105 (3)
N2—H2···O10.88 (3)2.46 (2)3.278 (7)156 (3)
N2—H2···O1'0.88 (3)2.05 (2)2.88 (1)158 (3)
N3—H3···N50.87 (3)2.48 (3)2.843 (4)106 (3)
N4—H4···O10.88 (3)2.08 (2)2.927 (8)162 (3)
N4—H4···O1'0.88 (3)2.30 (2)3.14 (1)160 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5382).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2003). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jiang, L., Feng, X.-L., Su, C.-Y., Chen, X.-M. & Lu, T.-B. (2007). Inorg. Chem.46, 2637–2644. [PubMed]
  • Jiang, L., Lu, T.-B. & Feng, X.-L. (2005). Inorg. Chem.44, 7056–7062. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography