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 August 1; 66(Pt 8): m1025.
Published online 2010 July 31. doi:  10.1107/S1600536810029181
PMCID: PMC3007476

Aqua(dimethylformamide){tris[(1-methyl-1H-benzimidazol-2-yl)methyl]amine}nickel(II) dipicrate

Abstract

In the title complex, [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2, the NiII ion is coordinated in a slightly distorted octa­hedral coordination evironment by an NiN4O2 ligand set. The tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine ligand is in a tetra­dentate mode while a coordinated water molecule and a dimethyl­formamide ligand complete the coordination. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds link the cation and one of the pictrate anions into four-component centrosymmetric clusters.

Related literature

For the biological activity of compounds containing a benzimid­azole core, see: Horton et al. (2003 [triangle]). For related structures, see Wu et al. (2005 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1025-scheme1.jpg

Experimental

Crystal data

  • [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2
  • M r = 1055.57
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1025-efi1.jpg
  • a = 12.0768 (3) Å
  • b = 13.2619 (4) Å
  • c = 15.3544 (4) Å
  • α = 108.583 (1)°
  • β = 95.703 (1)°
  • γ = 99.506 (1)°
  • V = 2268.36 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.52 mm−1
  • T = 153 K
  • 0.25 × 0.22 × 0.11 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.882, T max = 0.945
  • 18738 measured reflections
  • 8420 independent reflections
  • 5743 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.159
  • S = 1.18
  • 8420 reflections
  • 667 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.01 e Å−3
  • Δρmin = −1.24 e Å−3

Data collection: APEX2 (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810029181/lh5085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029181/lh5085Isup2.hkl

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

Acknowledgments

We are grateful for financially support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the ‘Long Yuan Qing Nian’ of Gansu Province is also acknowledged

supplementary crystallographic information

Comment

We are interested in tris(2-benzimidazolyl)alkanes and their derivatives and we have previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005). The benzimidazole core is of a wide interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The asymmetric unit of the title compound consists of an [Ni(Mentb)(DMF)(H2O)] cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine and two picrate anions (Fig.1). The NiII ion is coordinated in a slightly- distorted octahedral coordination evironment by NiN4O2 ligand set. The Mentb ligand coordinates in a tetradentate mode while a coordinated water and a dimethylformamide ligand complete the coordination. In the crystal structure, intermolecular O-H···O hydrogen bonds link the cation and one of the pictrate anions into four component centrosymmetric clusters (Fig. 2).

Experimental

To a stirred solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Ni(C6H2N3O7)2 (0.0103 g, 0.2 mmol) in MeOH (5 ml). A pale green crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a pale green solution that was allowed to evaporate at room temperature. Green crystals suitable for X-ray diffraction studies were obtained after three weeks (Yield, 62%). Elemental analysis found: C, 47.79%; H, 3.82%; N, 18.58%; calcd. for C42 H40 N14 O16 Ni: C, 47.82%; H, 3.79%; N, 18.51%.

Refinement

H atoms bonded to C atoms were placed in calculated positions and included in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The water H atoms were located in a difference Fourier map and refined with the restraint O-H = 0.85 (2)Å.

Figures

Fig. 1.
The asymmetric unit of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
Fig. 2.
Part of the crystal structure of the title compound, showing hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonging are shown.

Crystal data

[Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2Z = 2
Mr = 1055.57F(000) = 1092
Triclinic, P1Dx = 1.545 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.0768 (3) ÅCell parameters from 8420 reflections
b = 13.2619 (4) Åθ = 2.4–28.2°
c = 15.3544 (4) ŵ = 0.52 mm1
α = 108.583 (1)°T = 153 K
β = 95.703 (1)°Block, green
γ = 99.506 (1)°0.25 × 0.22 × 0.11 mm
V = 2268.36 (11) Å3

Data collection

Bruker SMART APEXII diffractometer8420 independent reflections
Radiation source: fine-focus sealed tube5743 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.882, Tmax = 0.945k = −16→16
18738 measured reflectionsl = −17→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159w = 1/[σ2(Fo2) + (0.0452P)2 + 5.4011P] where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.001
8420 reflectionsΔρmax = 1.01 e Å3
667 parametersΔρmin = −1.24 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (5)

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
Ni0.46074 (4)0.67214 (4)0.72572 (4)0.02153 (16)
O10.3577 (2)0.7136 (2)0.63281 (19)0.0281 (7)
O20.5213 (3)0.5564 (3)0.6231 (2)0.0274 (7)
O30.6467 (3)0.6084 (3)0.5008 (2)0.0476 (10)
O40.5367 (3)0.6964 (4)0.3971 (3)0.0792 (14)
O50.5862 (5)0.8686 (5)0.4310 (4)0.108 (2)
O60.9546 (4)1.0643 (3)0.5816 (3)0.0661 (13)
O71.0726 (4)0.9877 (4)0.6429 (3)0.0731 (14)
O80.9680 (4)0.6105 (4)0.5949 (4)0.0919 (17)
O90.7967 (4)0.5556 (4)0.6107 (4)0.0843 (15)
O100.2350 (3)0.3427 (3)0.9903 (2)0.0412 (8)
O110.3778 (3)0.5213 (3)0.9850 (2)0.0486 (10)
O120.2960 (3)0.6577 (4)1.0118 (3)0.0670 (12)
O13−0.0696 (3)0.6005 (3)0.8309 (3)0.0503 (9)
O14−0.1952 (3)0.4559 (3)0.8155 (2)0.0456 (9)
O15−0.0703 (4)0.2009 (4)0.9669 (3)0.0758 (14)
O160.0677 (4)0.1511 (3)0.8988 (4)0.0825 (16)
N10.6052 (3)0.7868 (3)0.7367 (2)0.0237 (7)
N20.7876 (3)0.8539 (3)0.7984 (2)0.0234 (8)
N30.3619 (3)0.5380 (3)0.7390 (2)0.0237 (8)
N40.3585 (3)0.3892 (3)0.7762 (2)0.0248 (8)
N50.4158 (3)0.7756 (3)0.8396 (2)0.0237 (8)
N60.4450 (3)0.8522 (3)0.9935 (2)0.0251 (8)
N70.5741 (3)0.6426 (3)0.8305 (2)0.0206 (7)
N80.2926 (3)0.7234 (3)0.4929 (2)0.0321 (9)
N90.6035 (4)0.7845 (5)0.4381 (3)0.0539 (13)
N100.9804 (4)0.9860 (4)0.5993 (3)0.0495 (12)
N110.8678 (4)0.6177 (4)0.5921 (3)0.0481 (11)
N120.2919 (3)0.5600 (4)0.9830 (3)0.0397 (10)
N13−0.0966 (3)0.5105 (3)0.8384 (3)0.0349 (9)
N140.0128 (4)0.2193 (4)0.9307 (3)0.0484 (12)
C10.6383 (3)0.8840 (3)0.7211 (3)0.0231 (9)
C20.5753 (4)0.9402 (3)0.6782 (3)0.0281 (10)
H2B0.49720.91190.65200.034*
C30.6314 (4)1.0377 (4)0.6758 (3)0.0357 (11)
H3A0.59111.07810.64770.043*
C40.7468 (4)1.0795 (4)0.7138 (4)0.0380 (11)
H4A0.78261.14720.71030.046*
C50.8102 (4)1.0252 (4)0.7563 (3)0.0339 (11)
H5A0.88831.05350.78220.041*
C60.7524 (3)0.9264 (3)0.7589 (3)0.0255 (9)
C70.6969 (3)0.7732 (3)0.7840 (3)0.0232 (9)
C80.6925 (3)0.6766 (3)0.8150 (3)0.0250 (9)
H8A0.71360.61630.76670.030*
H8B0.74680.69560.87330.030*
C90.5451 (3)0.5244 (3)0.8168 (3)0.0262 (9)
H9A0.56230.51270.87680.031*
H9B0.59030.48440.77270.031*
C100.4205 (3)0.4843 (3)0.7788 (3)0.0248 (9)
C110.2494 (3)0.3800 (3)0.7303 (3)0.0230 (9)
C120.1523 (4)0.2984 (4)0.7074 (3)0.0305 (10)
H12A0.15150.23370.72180.037*
C130.0562 (4)0.3171 (4)0.6622 (3)0.0318 (10)
H13A−0.01270.26400.64530.038*
C140.0588 (4)0.4132 (4)0.6410 (3)0.0318 (10)
H14A−0.00840.42320.61000.038*
C150.1555 (3)0.4924 (3)0.6637 (3)0.0265 (9)
H15A0.15650.55720.64960.032*
C160.2530 (3)0.4742 (3)0.7088 (3)0.0232 (9)
C170.5556 (4)0.7092 (4)0.9249 (3)0.0279 (10)
H17A0.52760.66010.95850.033*
H17B0.62910.75600.96100.033*
C180.4724 (3)0.7786 (3)0.9191 (3)0.0221 (9)
C190.3643 (3)0.8988 (3)0.9595 (3)0.0263 (9)
C200.3085 (4)0.9796 (4)1.0048 (3)0.0350 (11)
H20A0.32101.01171.07070.042*
C210.2339 (4)1.0103 (4)0.9487 (3)0.0344 (11)
H21A0.19471.06580.97650.041*
C220.2151 (4)0.9617 (4)0.8520 (3)0.0360 (11)
H22A0.16270.98450.81580.043*
C230.2704 (3)0.8811 (4)0.8072 (3)0.0313 (10)
H23A0.25690.84820.74130.038*
C240.3464 (3)0.8508 (3)0.8632 (3)0.0233 (9)
C250.9037 (4)0.8644 (4)0.8443 (3)0.0360 (11)
H25A0.90670.80290.86610.054*
H25B0.92530.93260.89750.054*
H25C0.95670.86480.79990.054*
C260.3955 (4)0.3098 (4)0.8132 (3)0.0334 (10)
H26A0.47580.33580.84190.050*
H26B0.38630.24020.76250.050*
H26C0.34940.29990.86000.050*
C270.4860 (4)0.8732 (4)1.0919 (3)0.0327 (10)
H27A0.54290.82971.09710.049*
H27B0.42210.85341.12200.049*
H27C0.52050.95061.12260.049*
C280.3449 (3)0.6785 (3)0.5465 (3)0.0247 (9)
H28A0.37400.61610.51720.030*
C290.2483 (7)0.8196 (6)0.5310 (4)0.088 (3)
H29A0.26210.84270.59920.132*
H29B0.16620.80370.50870.132*
H29C0.28620.87780.51120.132*
C300.2785 (4)0.6789 (4)0.3916 (3)0.0319 (10)
H30A0.31090.61360.37300.048*
H30B0.31770.73330.36820.048*
H30C0.19730.65980.36560.048*
C310.7227 (4)0.6930 (4)0.5180 (3)0.0322 (10)
C320.7101 (4)0.7865 (4)0.4924 (3)0.0310 (10)
C330.7918 (4)0.8803 (4)0.5177 (3)0.0354 (11)
H33A0.77750.94060.50100.042*
C340.8956 (4)0.8854 (4)0.5681 (3)0.0311 (10)
C350.9189 (4)0.7981 (4)0.5902 (3)0.0323 (10)
H35A0.99200.80140.62160.039*
C360.8360 (4)0.7063 (4)0.5667 (3)0.0302 (10)
C370.1626 (4)0.3812 (4)0.9551 (3)0.0298 (10)
C380.1809 (3)0.4884 (4)0.9463 (3)0.0313 (10)
C390.0991 (4)0.5297 (4)0.9091 (3)0.0294 (10)
H39A0.11700.60030.90480.035*
C40−0.0101 (3)0.4675 (4)0.8779 (3)0.0275 (10)
C41−0.0389 (4)0.3658 (4)0.8866 (3)0.0326 (11)
H41A−0.11490.32500.86780.039*
C420.0447 (4)0.3260 (4)0.9229 (3)0.0291 (10)
H2D0.569 (4)0.575 (5)0.590 (4)0.07 (2)*
H2C0.479 (5)0.496 (3)0.590 (4)0.10 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni0.0232 (3)0.0219 (3)0.0210 (3)0.0076 (2)0.0037 (2)0.0080 (2)
O10.0310 (15)0.0346 (17)0.0204 (15)0.0126 (13)0.0020 (12)0.0098 (13)
O20.0276 (16)0.0270 (17)0.0267 (16)0.0038 (14)0.0095 (14)0.0075 (14)
O30.054 (2)0.044 (2)0.0298 (18)−0.0176 (18)0.0120 (16)0.0046 (16)
O40.042 (2)0.099 (4)0.079 (3)0.006 (3)−0.011 (2)0.017 (3)
O50.125 (5)0.082 (4)0.100 (4)0.054 (4)−0.051 (3)0.014 (3)
O60.102 (3)0.024 (2)0.072 (3)−0.002 (2)0.042 (3)0.0137 (19)
O70.061 (3)0.074 (3)0.059 (3)−0.031 (2)−0.011 (2)0.018 (2)
O80.082 (3)0.098 (4)0.131 (5)0.051 (3)0.016 (3)0.070 (4)
O90.105 (4)0.055 (3)0.112 (4)0.008 (3)0.020 (3)0.058 (3)
O100.0372 (18)0.059 (2)0.0392 (19)0.0253 (17)0.0060 (15)0.0247 (17)
O110.0251 (17)0.081 (3)0.045 (2)0.0168 (18)0.0085 (15)0.025 (2)
O120.043 (2)0.049 (3)0.102 (4)−0.0030 (19)0.006 (2)0.025 (2)
O130.051 (2)0.055 (2)0.059 (2)0.0289 (19)0.0080 (18)0.030 (2)
O140.0326 (18)0.056 (2)0.043 (2)0.0185 (17)−0.0091 (15)0.0090 (17)
O150.099 (4)0.049 (3)0.073 (3)−0.007 (3)0.019 (3)0.022 (2)
O160.064 (3)0.041 (2)0.135 (4)0.026 (2)−0.011 (3)0.019 (3)
N10.0284 (18)0.0211 (18)0.0252 (18)0.0109 (15)0.0071 (15)0.0093 (15)
N20.0169 (16)0.0262 (19)0.0242 (18)0.0012 (14)0.0002 (14)0.0071 (15)
N30.0206 (16)0.0245 (19)0.0245 (18)0.0066 (14)0.0024 (14)0.0058 (15)
N40.0297 (18)0.0213 (18)0.0274 (19)0.0073 (15)0.0054 (15)0.0125 (15)
N50.0228 (17)0.0254 (19)0.0249 (18)0.0103 (15)0.0053 (14)0.0080 (15)
N60.0285 (18)0.0266 (19)0.0189 (17)0.0102 (15)0.0052 (14)0.0033 (15)
N70.0196 (16)0.0240 (18)0.0198 (17)0.0060 (14)0.0024 (13)0.0091 (14)
N80.040 (2)0.033 (2)0.0263 (19)0.0138 (18)0.0021 (16)0.0118 (17)
N90.051 (3)0.071 (4)0.035 (2)0.027 (3)0.004 (2)0.006 (2)
N100.067 (3)0.030 (2)0.042 (3)−0.010 (2)0.019 (2)0.007 (2)
N110.065 (3)0.036 (3)0.051 (3)0.015 (2)0.011 (2)0.023 (2)
N120.032 (2)0.052 (3)0.041 (2)0.008 (2)0.0115 (18)0.022 (2)
N130.042 (2)0.043 (2)0.027 (2)0.025 (2)0.0044 (17)0.0135 (18)
N140.051 (3)0.035 (3)0.050 (3)0.011 (2)−0.013 (2)0.007 (2)
C10.022 (2)0.020 (2)0.026 (2)0.0019 (17)0.0052 (17)0.0065 (17)
C20.035 (2)0.027 (2)0.026 (2)0.0087 (19)0.0065 (19)0.0117 (19)
C30.045 (3)0.030 (3)0.037 (3)0.013 (2)0.008 (2)0.015 (2)
C40.040 (3)0.025 (2)0.051 (3)0.001 (2)0.010 (2)0.019 (2)
C50.032 (2)0.028 (2)0.039 (3)0.004 (2)0.006 (2)0.008 (2)
C60.029 (2)0.024 (2)0.023 (2)0.0092 (18)0.0070 (18)0.0060 (18)
C70.030 (2)0.024 (2)0.021 (2)0.0123 (18)0.0068 (17)0.0095 (17)
C80.022 (2)0.031 (2)0.025 (2)0.0084 (18)0.0023 (17)0.0122 (18)
C90.028 (2)0.026 (2)0.032 (2)0.0118 (18)0.0046 (18)0.0161 (19)
C100.028 (2)0.024 (2)0.025 (2)0.0130 (18)0.0053 (17)0.0083 (18)
C110.028 (2)0.024 (2)0.021 (2)0.0064 (17)0.0108 (17)0.0094 (17)
C120.032 (2)0.025 (2)0.038 (3)0.0050 (19)0.013 (2)0.013 (2)
C130.029 (2)0.029 (2)0.040 (3)0.0050 (19)0.011 (2)0.014 (2)
C140.024 (2)0.036 (3)0.035 (2)0.0061 (19)0.0025 (19)0.012 (2)
C150.027 (2)0.023 (2)0.033 (2)0.0069 (18)0.0065 (18)0.0112 (19)
C160.029 (2)0.021 (2)0.023 (2)0.0065 (17)0.0099 (17)0.0100 (17)
C170.033 (2)0.033 (2)0.020 (2)0.0121 (19)0.0049 (18)0.0085 (18)
C180.024 (2)0.025 (2)0.021 (2)0.0069 (17)0.0024 (16)0.0121 (17)
C190.028 (2)0.024 (2)0.029 (2)0.0096 (18)0.0071 (18)0.0091 (18)
C200.036 (2)0.039 (3)0.028 (2)0.015 (2)0.010 (2)0.004 (2)
C210.037 (2)0.037 (3)0.034 (3)0.026 (2)0.009 (2)0.009 (2)
C220.031 (2)0.042 (3)0.039 (3)0.019 (2)0.007 (2)0.014 (2)
C230.026 (2)0.036 (3)0.028 (2)0.0089 (19)0.0006 (18)0.005 (2)
C240.0205 (19)0.024 (2)0.024 (2)0.0066 (17)0.0040 (16)0.0046 (17)
C250.030 (2)0.042 (3)0.036 (3)0.010 (2)0.001 (2)0.014 (2)
C260.039 (3)0.029 (2)0.037 (3)0.010 (2)0.006 (2)0.017 (2)
C270.042 (3)0.035 (3)0.017 (2)0.010 (2)0.0013 (19)0.0035 (19)
C280.027 (2)0.023 (2)0.029 (2)0.0078 (18)0.0027 (18)0.0147 (18)
C290.139 (7)0.097 (6)0.041 (3)0.098 (5)−0.003 (4)0.010 (3)
C300.035 (2)0.042 (3)0.021 (2)0.004 (2)0.0017 (18)0.017 (2)
C310.036 (2)0.031 (3)0.027 (2)0.002 (2)0.017 (2)0.006 (2)
C320.032 (2)0.040 (3)0.024 (2)0.017 (2)0.0084 (18)0.010 (2)
C330.052 (3)0.033 (3)0.028 (2)0.014 (2)0.014 (2)0.015 (2)
C340.038 (2)0.021 (2)0.031 (2)−0.0034 (19)0.011 (2)0.0076 (19)
C350.032 (2)0.034 (3)0.030 (2)0.006 (2)0.0072 (19)0.009 (2)
C360.042 (3)0.026 (2)0.029 (2)0.012 (2)0.011 (2)0.0151 (19)
C370.033 (2)0.040 (3)0.022 (2)0.021 (2)0.0073 (18)0.011 (2)
C380.024 (2)0.045 (3)0.027 (2)0.012 (2)0.0035 (18)0.013 (2)
C390.036 (2)0.035 (3)0.024 (2)0.015 (2)0.0112 (19)0.0133 (19)
C400.030 (2)0.036 (3)0.023 (2)0.020 (2)0.0046 (18)0.0118 (19)
C410.035 (2)0.034 (3)0.025 (2)0.015 (2)0.0026 (19)0.001 (2)
C420.035 (2)0.029 (2)0.029 (2)0.017 (2)0.0036 (19)0.0129 (19)

Geometric parameters (Å, °)

Ni—N52.035 (3)C8—H8A0.9900
Ni—N32.052 (4)C8—H8B0.9900
Ni—O12.063 (3)C9—C101.500 (6)
Ni—N12.071 (3)C9—H9A0.9900
Ni—O22.106 (3)C9—H9B0.9900
Ni—N72.181 (3)C11—C161.384 (6)
O1—C281.240 (5)C11—C121.388 (6)
O2—H2D0.86 (2)C12—C131.391 (6)
O2—H2C0.85 (2)C12—H12A0.9500
O3—O30.000 (9)C13—C141.409 (6)
O3—C311.263 (5)C13—H13A0.9500
O4—N91.237 (6)C14—C151.366 (6)
O5—N91.204 (7)C14—H14A0.9500
O6—N101.232 (6)C15—C161.401 (6)
O7—N101.234 (6)C15—H15A0.9500
O8—N111.227 (6)C17—C181.485 (6)
O9—N111.209 (6)C17—H17A0.9900
O10—C371.244 (5)C17—H17B0.9900
O11—N121.233 (5)C19—C241.389 (6)
O12—N121.219 (6)C19—C201.394 (6)
O13—N131.230 (5)C20—C211.382 (6)
O14—N131.239 (5)C20—H20A0.9500
O15—N141.221 (6)C21—C221.395 (6)
O16—N141.216 (6)C21—H21A0.9500
N1—C71.333 (5)C22—C231.385 (6)
N1—C11.387 (5)C22—H22A0.9500
N2—C71.345 (5)C23—C241.390 (6)
N2—C61.388 (5)C23—H23A0.9500
N2—C251.470 (5)C25—H25A0.9800
N3—C101.318 (5)C25—H25B0.9800
N3—C161.387 (5)C25—H25C0.9800
N4—C101.343 (5)C26—H26A0.9800
N4—C111.399 (5)C26—H26B0.9800
N4—C261.455 (5)C26—H26C0.9800
N5—C181.324 (5)C27—H27A0.9800
N5—C241.390 (5)C27—H27B0.9800
N6—C181.355 (5)C27—H27C0.9800
N6—C191.381 (5)C28—H28A0.9500
N6—C271.465 (5)C29—H29A0.9800
N7—C91.490 (5)C29—H29B0.9800
N7—C81.493 (5)C29—H29C0.9800
N7—C171.498 (5)C30—H30A0.9800
N8—C281.329 (5)C30—H30B0.9800
N8—C291.438 (7)C30—H30C0.9800
N8—C301.457 (5)C31—O31.263 (5)
N9—C321.454 (6)C31—C321.441 (7)
N10—C341.450 (6)C31—C361.447 (6)
N11—C361.446 (6)C32—C331.372 (7)
N12—C381.450 (6)C33—C341.386 (7)
N13—C401.441 (5)C33—H33A0.9500
N14—C421.450 (6)C34—C351.369 (6)
C1—C61.388 (6)C35—C361.364 (6)
C1—C21.403 (6)C35—H35A0.9500
C2—C31.371 (6)C37—C421.446 (6)
C2—H2B0.9500C37—C381.454 (7)
C3—C41.403 (7)C38—C391.367 (6)
C3—H3A0.9500C39—C401.382 (6)
C4—C51.383 (7)C39—H39A0.9500
C4—H4A0.9500C40—C411.388 (7)
C5—C61.394 (6)C41—C421.363 (6)
C5—H5A0.9500C41—H41A0.9500
C7—C81.498 (6)
N5—Ni—N392.81 (14)C14—C13—H13A119.3
N5—Ni—O193.80 (12)C15—C14—C13121.8 (4)
N3—Ni—O1104.09 (12)C15—C14—H14A119.1
N5—Ni—N190.52 (13)C13—C14—H14A119.1
N3—Ni—N1158.76 (13)C14—C15—C16117.4 (4)
O1—Ni—N196.60 (13)C14—C15—H15A121.3
N5—Ni—O2170.87 (13)C16—C15—H15A121.3
N3—Ni—O284.00 (13)C11—C16—N3109.2 (4)
O1—Ni—O295.28 (12)C11—C16—C15120.5 (4)
N1—Ni—O289.44 (13)N3—C16—C15130.3 (4)
N5—Ni—N782.85 (13)C18—C17—N7112.0 (3)
N3—Ni—N779.47 (12)C18—C17—H17A109.2
O1—Ni—N7175.27 (12)N7—C17—H17A109.2
N1—Ni—N780.16 (13)C18—C17—H17B109.2
O2—Ni—N788.15 (12)N7—C17—H17B109.2
C28—O1—Ni128.2 (3)H17A—C17—H17B107.9
Ni—O2—H2D122 (4)N5—C18—N6111.8 (3)
Ni—O2—H2C121 (5)N5—C18—C17123.5 (4)
H2D—O2—H2C108 (6)N6—C18—C17124.7 (3)
O3—O3—C310(10)N6—C19—C24106.3 (3)
C7—N1—C1105.8 (3)N6—C19—C20131.3 (4)
C7—N1—Ni112.8 (3)C24—C19—C20122.3 (4)
C1—N1—Ni140.8 (3)C21—C20—C19116.4 (4)
C7—N2—C6106.9 (3)C21—C20—H20A121.8
C7—N2—C25127.8 (4)C19—C20—H20A121.8
C6—N2—C25125.3 (4)C20—C21—C22121.4 (4)
C10—N3—C16105.7 (4)C20—C21—H21A119.3
C10—N3—Ni113.2 (3)C22—C21—H21A119.3
C16—N3—Ni140.4 (3)C23—C22—C21122.1 (4)
C10—N4—C11106.6 (3)C23—C22—H22A119.0
C10—N4—C26127.6 (3)C21—C22—H22A119.0
C11—N4—C26125.8 (3)C22—C23—C24116.8 (4)
C18—N5—C24106.2 (3)C22—C23—H23A121.6
C18—N5—Ni113.2 (3)C24—C23—H23A121.6
C24—N5—Ni140.6 (3)C19—C24—C23121.0 (4)
C18—N6—C19107.2 (3)C19—C24—N5108.5 (3)
C18—N6—C27126.9 (4)C23—C24—N5130.5 (4)
C19—N6—C27125.8 (3)N2—C25—H25A109.5
C9—N7—C8111.9 (3)N2—C25—H25B109.5
C9—N7—C17110.7 (3)H25A—C25—H25B109.5
C8—N7—C17111.3 (3)N2—C25—H25C109.5
C9—N7—Ni107.7 (2)H25A—C25—H25C109.5
C8—N7—Ni106.6 (2)H25B—C25—H25C109.5
C17—N7—Ni108.4 (2)N4—C26—H26A109.5
C28—N8—C29122.1 (4)N4—C26—H26B109.5
C28—N8—C30121.8 (4)H26A—C26—H26B109.5
C29—N8—C30116.0 (4)N4—C26—H26C109.5
O5—N9—O4122.3 (5)H26A—C26—H26C109.5
O5—N9—C32118.3 (5)H26B—C26—H26C109.5
O4—N9—C32119.3 (5)N6—C27—H27A109.5
O6—N10—O7124.6 (5)N6—C27—H27B109.5
O6—N10—C34117.6 (5)H27A—C27—H27B109.5
O7—N10—C34117.7 (5)N6—C27—H27C109.5
O9—N11—O8122.9 (5)H27A—C27—H27C109.5
O9—N11—C36119.7 (5)H27B—C27—H27C109.5
O8—N11—C36117.4 (5)O1—C28—N8123.7 (4)
O12—N12—O11122.3 (4)O1—C28—H28A118.2
O12—N12—C38117.8 (4)N8—C28—H28A118.2
O11—N12—C38119.9 (4)N8—C29—H29A109.5
O13—N13—O14123.1 (4)N8—C29—H29B109.5
O13—N13—C40118.5 (4)H29A—C29—H29B109.5
O14—N13—C40118.4 (4)N8—C29—H29C109.5
O16—N14—O15122.8 (5)H29A—C29—H29C109.5
O16—N14—C42118.8 (5)H29B—C29—H29C109.5
O15—N14—C42118.4 (5)N8—C30—H30A109.5
N1—C1—C6108.8 (4)N8—C30—H30B109.5
N1—C1—C2130.5 (4)H30A—C30—H30B109.5
C6—C1—C2120.8 (4)N8—C30—H30C109.5
C3—C2—C1117.0 (4)H30A—C30—H30C109.5
C3—C2—H2B121.5H30B—C30—H30C109.5
C1—C2—H2B121.5O3—C31—O30.0 (4)
C2—C3—C4121.7 (4)O3—C31—C32125.8 (4)
C2—C3—H3A119.1O3—C31—C32125.8 (4)
C4—C3—H3A119.1O3—C31—C36122.6 (4)
C5—C4—C3122.0 (4)O3—C31—C36122.6 (4)
C5—C4—H4A119.0C32—C31—C36111.6 (4)
C3—C4—H4A119.0C33—C32—C31124.4 (4)
C4—C5—C6115.9 (4)C33—C32—N9116.6 (5)
C4—C5—H5A122.0C31—C32—N9119.0 (4)
C6—C5—H5A122.0C32—C33—C34118.7 (4)
N2—C6—C1106.2 (4)C32—C33—H33A120.7
N2—C6—C5131.1 (4)C34—C33—H33A120.7
C1—C6—C5122.6 (4)C35—C34—C33121.4 (4)
N1—C7—N2112.3 (4)C35—C34—N10119.4 (4)
N1—C7—C8120.9 (4)C33—C34—N10119.1 (4)
N2—C7—C8126.8 (3)C36—C35—C34119.2 (4)
N7—C8—C7108.1 (3)C36—C35—H35A120.4
N7—C8—H8A110.1C34—C35—H35A120.4
C7—C8—H8A110.1C35—C36—N11115.7 (4)
N7—C8—H8B110.1C35—C36—C31124.5 (4)
C7—C8—H8B110.1N11—C36—C31119.8 (4)
H8A—C8—H8B108.4O10—C37—C42123.3 (4)
N7—C9—C10107.8 (3)O10—C37—C38125.8 (4)
N7—C9—H9A110.1C42—C37—C38110.7 (4)
C10—C9—H9A110.1C39—C38—N12116.6 (4)
N7—C9—H9B110.1C39—C38—C37124.7 (4)
C10—C9—H9B110.1N12—C38—C37118.7 (4)
H9A—C9—H9B108.5C38—C39—C40119.2 (4)
N3—C10—N4112.9 (4)C38—C39—H39A120.4
N3—C10—C9122.2 (4)C40—C39—H39A120.4
N4—C10—C9124.8 (4)C39—C40—C41121.3 (4)
C16—C11—C12123.0 (4)C39—C40—N13119.4 (4)
C16—C11—N4105.7 (3)C41—C40—N13119.3 (4)
C12—C11—N4131.3 (4)C42—C41—C40118.3 (4)
C11—C12—C13115.9 (4)C42—C41—H41A120.8
C11—C12—H12A122.0C40—C41—H41A120.8
C13—C12—H12A122.0C41—C42—C37125.8 (4)
C12—C13—C14121.4 (4)C41—C42—N14117.4 (4)
C12—C13—H13A119.3C37—C42—N14116.9 (4)
N5—Ni—O1—C28179.5 (3)C12—C11—C16—C151.4 (6)
N3—Ni—O1—C28−86.7 (4)N4—C11—C16—C15−178.5 (4)
N1—Ni—O1—C2888.5 (4)C10—N3—C16—C11−1.1 (5)
O2—Ni—O1—C28−1.6 (4)Ni—N3—C16—C11167.7 (3)
N7—Ni—O1—C28134.9 (14)C10—N3—C16—C15178.6 (4)
N5—Ni—N1—C794.7 (3)Ni—N3—C16—C15−12.5 (7)
N3—Ni—N1—C7−4.4 (5)C14—C15—C16—C11−1.0 (6)
O1—Ni—N1—C7−171.4 (3)C14—C15—C16—N3179.2 (4)
O2—Ni—N1—C7−76.2 (3)C9—N7—C17—C18−121.2 (4)
N7—Ni—N1—C712.1 (3)C8—N7—C17—C18113.8 (4)
N5—Ni—N1—C1−74.3 (4)Ni—N7—C17—C18−3.2 (4)
N3—Ni—N1—C1−173.4 (4)C24—N5—C18—N6−0.6 (5)
O1—Ni—N1—C119.6 (4)Ni—N5—C18—N6176.9 (3)
O2—Ni—N1—C1114.8 (4)C24—N5—C18—C17179.4 (4)
N7—Ni—N1—C1−156.9 (5)Ni—N5—C18—C17−3.1 (5)
N5—Ni—N3—C10−100.0 (3)C19—N6—C18—N50.7 (5)
O1—Ni—N3—C10165.4 (3)C27—N6—C18—N5176.5 (4)
N1—Ni—N3—C10−1.3 (6)C19—N6—C18—C17−179.3 (4)
O2—Ni—N3—C1071.4 (3)C27—N6—C18—C17−3.6 (7)
N7—Ni—N3—C10−17.8 (3)N7—C17—C18—N54.4 (6)
N5—Ni—N3—C1691.7 (4)N7—C17—C18—N6−175.5 (4)
O1—Ni—N3—C16−2.9 (4)C18—N6—C19—C24−0.5 (5)
N1—Ni—N3—C16−169.6 (4)C27—N6—C19—C24−176.3 (4)
O2—Ni—N3—C16−96.9 (4)C18—N6—C19—C20−178.9 (5)
N7—Ni—N3—C16173.9 (4)C27—N6—C19—C205.2 (8)
N3—Ni—N5—C1879.7 (3)N6—C19—C20—C21177.9 (5)
O1—Ni—N5—C18−175.9 (3)C24—C19—C20—C21−0.3 (7)
N1—Ni—N5—C18−79.3 (3)C19—C20—C21—C220.8 (7)
O2—Ni—N5—C1810.5 (10)C20—C21—C22—C23−0.6 (8)
N7—Ni—N5—C180.7 (3)C21—C22—C23—C24−0.2 (7)
N3—Ni—N5—C24−104.1 (4)N6—C19—C24—C23−179.1 (4)
O1—Ni—N5—C240.2 (4)C20—C19—C24—C23−0.5 (7)
N1—Ni—N5—C2496.9 (4)N6—C19—C24—N50.1 (5)
O2—Ni—N5—C24−173.4 (7)C20—C19—C24—N5178.8 (4)
N7—Ni—N5—C24176.9 (4)C22—C23—C24—C190.7 (7)
N5—Ni—N7—C9121.3 (3)C22—C23—C24—N5−178.3 (4)
N3—Ni—N7—C927.1 (2)C18—N5—C24—C190.3 (5)
O1—Ni—N7—C9166.3 (14)Ni—N5—C24—C19−176.0 (3)
N1—Ni—N7—C9−146.9 (3)C18—N5—C24—C23179.4 (5)
O2—Ni—N7—C9−57.1 (3)Ni—N5—C24—C233.1 (8)
N5—Ni—N7—C8−118.4 (3)Ni—O1—C28—N8−167.6 (3)
N3—Ni—N7—C8147.3 (3)C29—N8—C28—O11.6 (8)
O1—Ni—N7—C8−73.5 (15)C30—N8—C28—O1−179.4 (4)
N1—Ni—N7—C8−26.6 (2)O3—O3—C31—C320.00 (4)
O2—Ni—N7—C863.1 (2)O3—O3—C31—C360.00 (17)
N5—Ni—N7—C171.5 (3)O3—C31—C32—C33175.3 (4)
N3—Ni—N7—C17−92.8 (3)O3—C31—C32—C33175.3 (4)
O1—Ni—N7—C1746.4 (16)C36—C31—C32—C33−5.2 (6)
N1—Ni—N7—C1793.2 (3)O3—C31—C32—N9−3.0 (7)
O2—Ni—N7—C17−177.0 (3)O3—C31—C32—N9−3.0 (7)
C7—N1—C1—C61.1 (4)C36—C31—C32—N9176.5 (4)
Ni—N1—C1—C6170.6 (3)O5—N9—C32—C33−11.2 (7)
C7—N1—C1—C2−177.1 (4)O4—N9—C32—C33165.0 (5)
Ni—N1—C1—C2−7.6 (8)O5—N9—C32—C31167.2 (5)
N1—C1—C2—C3177.8 (4)O4—N9—C32—C31−16.6 (7)
C6—C1—C2—C3−0.2 (6)C31—C32—C33—C342.7 (7)
C1—C2—C3—C40.4 (7)N9—C32—C33—C34−178.9 (4)
C2—C3—C4—C5−0.5 (8)C32—C33—C34—C352.1 (7)
C3—C4—C5—C60.2 (7)C32—C33—C34—N10−176.9 (4)
C7—N2—C6—C1−0.2 (4)O6—N10—C34—C35−176.9 (4)
C25—N2—C6—C1178.2 (4)O7—N10—C34—C352.0 (7)
C7—N2—C6—C5177.5 (4)O6—N10—C34—C332.1 (7)
C25—N2—C6—C5−4.1 (7)O7—N10—C34—C33−179.0 (4)
N1—C1—C6—N2−0.6 (5)C33—C34—C35—C36−3.8 (7)
C2—C1—C6—N2177.8 (4)N10—C34—C35—C36175.2 (4)
N1—C1—C6—C5−178.5 (4)C34—C35—C36—N11179.7 (4)
C2—C1—C6—C5−0.1 (6)C34—C35—C36—C310.7 (7)
C4—C5—C6—N2−177.2 (4)O9—N11—C36—C35149.3 (5)
C4—C5—C6—C10.1 (7)O8—N11—C36—C35−29.7 (7)
C1—N1—C7—N2−1.3 (5)O9—N11—C36—C31−31.7 (7)
Ni—N1—C7—N2−174.1 (3)O8—N11—C36—C31149.3 (5)
C1—N1—C7—C8178.9 (4)O3—C31—C36—C35−177.0 (4)
Ni—N1—C7—C86.1 (5)O3—C31—C36—C35−177.0 (4)
C6—N2—C7—N11.0 (5)C32—C31—C36—C353.5 (6)
C25—N2—C7—N1−177.4 (4)O3—C31—C36—N114.1 (7)
C6—N2—C7—C8−179.3 (4)O3—C31—C36—N114.1 (7)
C25—N2—C7—C82.4 (7)C32—C31—C36—N11−175.4 (4)
C9—N7—C8—C7152.8 (3)O12—N12—C38—C3927.7 (6)
C17—N7—C8—C7−82.8 (4)O11—N12—C38—C39−152.9 (4)
Ni—N7—C8—C735.2 (4)O12—N12—C38—C37−149.4 (5)
N1—C7—C8—N7−29.5 (5)O11—N12—C38—C3729.9 (6)
N2—C7—C8—N7150.7 (4)O10—C37—C38—C39−178.5 (4)
C8—N7—C9—C10−147.5 (3)C42—C37—C38—C39−2.4 (6)
C17—N7—C9—C1087.8 (4)O10—C37—C38—N12−1.6 (7)
Ni—N7—C9—C10−30.6 (4)C42—C37—C38—N12174.5 (4)
C16—N3—C10—N40.6 (5)N12—C38—C39—C40−176.3 (4)
Ni—N3—C10—N4−171.7 (3)C37—C38—C39—C400.7 (7)
C16—N3—C10—C9177.0 (4)C38—C39—C40—C412.3 (6)
Ni—N3—C10—C94.7 (5)C38—C39—C40—N13−179.8 (4)
C11—N4—C10—N30.2 (5)O13—N13—C40—C392.2 (6)
C26—N4—C10—N3−180.0 (4)O14—N13—C40—C39−176.2 (4)
C11—N4—C10—C9−176.2 (4)O13—N13—C40—C41−179.8 (4)
C26—N4—C10—C93.7 (7)O14—N13—C40—C411.8 (6)
N7—C9—C10—N319.0 (5)C39—C40—C41—C42−3.0 (6)
N7—C9—C10—N4−165.0 (4)N13—C40—C41—C42179.0 (4)
C10—N4—C11—C16−0.9 (4)C40—C41—C42—C371.0 (7)
C26—N4—C11—C16179.3 (4)C40—C41—C42—N14−179.6 (4)
C10—N4—C11—C12179.2 (4)O10—C37—C42—C41177.8 (4)
C26—N4—C11—C12−0.6 (7)C38—C37—C42—C411.6 (6)
C16—C11—C12—C13−1.0 (6)O10—C37—C42—N14−1.6 (7)
N4—C11—C12—C13178.9 (4)C38—C37—C42—N14−177.8 (4)
C11—C12—C13—C140.3 (7)O16—N14—C42—C41128.6 (5)
C12—C13—C14—C15−0.1 (7)O15—N14—C42—C41−49.3 (6)
C13—C14—C15—C160.4 (7)O16—N14—C42—C37−51.9 (6)
C12—C11—C16—N3−178.8 (4)O15—N14—C42—C37130.2 (5)
N4—C11—C16—N31.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2D···O30.86 (2)1.86 (2)2.708 (4)169 (6)
O2—H2C···O3i0.85 (2)1.95 (3)2.763 (4)160 (7)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5085).

References

  • Bruker (2000). APEX2 and SAINT Bruker AXS Inc., Madison,Wisconsin, USA
  • Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev.103, 893–930. [PubMed]
  • Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Wu, H. L., Huang, X. C., Yuan, J. K., Li, K., Ding, J., Yun, R. R., Dong, W. K. & Fan, X. Y. (2009). J. Coord. Chem.62, 3446–3453.
  • Wu, H. L., Ying, W., Pen, L., Gao, Y. C. & Yu, K. B. (2005). Synth. React. Inorg. Met.-Org. Chem.34, 553–558.

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