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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m20–m21.
Published online 2008 December 6. doi:  10.1107/S1600536808040476
PMCID: PMC2967869

cis-Bis{1-[(4-nitro­phen­yl)diazen­yl]-2-naphtholato}dipyridine­nickel(II)1

Abstract

In the title compound, [Ni(C16H10N3O3)2(C5H5N)2], the NiII cation is in a distorted octa­hedral NiN4O2 coordination by two independent bidentate 1-[(4-nitro­phen­yl)diazen­yl]-2-naph­thol­ate anions and two pyridine ligands. C—H(...)O inter­actions between aromatic rings and the O atoms of the nitro substituents build up a two-dimensional supra­molecular arrangement parallel to (100).

Related literature

For background on metal azo complexes, see: Carella et al. (2007 [triangle]); Kulikovska et al. (2007 [triangle]); Patnaik et al. (2007 [triangle]); Leng et al. (2001 [triangle]). For bond lengths, see: Abildgaard et al. (2006 [triangle]). For hydrogen bonds, see: Jeffrey & Saenger (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00m20-scheme1.jpg

Experimental

Crystal data

  • [Ni(C16H10N3O3)2(C5H5N)2]
  • M r = 801.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m20-efi5.jpg
  • a = 11.719 (2) Å
  • b = 18.885 (4) Å
  • c = 16.922 (3) Å
  • β = 93.04 (3)°
  • V = 3740.0 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 295 (2) K
  • 0.37 × 0.18 × 0.15 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.814, T max = 0.918
  • 64998 measured reflections
  • 6566 independent reflections
  • 4859 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.090
  • S = 1.05
  • 6566 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: PHICHI (Duisenberg et al., 2000 [triangle]); data reduction: EVALCCD (Duisenberg et al., 2003 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]) and WinGX (Farrugia, 1999 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040476/wm2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040476/wm2206Isup2.hkl

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

Acknowledgments

X-ray diffraction measurements were performed in the Laboratório de Difração de Raios X at the Universidade Federal Fluminense (LDRX-UFF), Niterói, Brazil. The authors thank Professor J. A. P. Bonapace for the initial reagents, CAPES, CNPq and FAPERJ for financial support, and the co-editor for his help in the improvement of the manuscript.

supplementary crystallographic information

Comment

Metal complexes with azo ligands show interesting chemical and physical properties and are of interest as new materials, for example in bioinorganic and coordination chemistry, as well as in biological systems which can lead to the development of new products with specific properties (Carella et al., 2007; Kulikovska et al., 2007; Patnaik et al., 2007; Leng et al., 2001). In this work the structure of the title molecule, [Ni(C16H10N3O3)2(C5H5N)2], (I) is reported.

Fig. 1 shows the molecular structure of compound (I). The NiII cation is octahedrally coordinated by four N and two O atoms with only slight distortion from the ideal coordination geometry. The two independent 1-[(4-nitrophenyl)diazenyl]-2-naphtholate ligands are bidentate and provide each one N atom from the azene moiety and one naphtolate O atom. The coordination is completed by the two pyridine N atoms. The Ni—N and Ni—O distances (Table 1) are in the typical ranges and like all other interatomic distances are in good agreement with literature data (Abildgaard et al., 2006).

The crystal packing is accomplished by two non-classical intermolecular C—H···O hydrogen bonds (Jeffrey & Saenger, 1991), forming a two-dimensional arrangement parallel to (100) (Fig. 2).

Experimental

To a mixture of 10.0 ml of MeOH and 10.0 ml of pyridine, 0.058 g (0.2 mmol) of 4-nitrophenylazo-2-naphthole was added with continuous stirring at room temperature. After stirring for 20 min, 0.025 g (0.1 mmol) of Ni(II) acetate were added. Stirring was maintained for 24 h. The solution was filtered off and red crystals of (I) with a block habit and up to 0.4 mm maximum size were obtained by slow evaporation of the mixture at room temperature. Melting point: 473 K; C, H, N analysis (%): calc., C, 62.94; H, 3.77; N, 13.98; found, C, 64.11; H, 3.91; N, 12.61.

Refinement

The H atoms of the naphthyl, pyridine and phenyl rings were fixed geometrically at a distance of 0.93 Å and were refined in the riding model approximation with Uiso(H) = 1.2×Ueq of the parent C atom.

Figures

Fig. 1.
ORTEP plot of the title molecule, (I). Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
View of the intermolecular H-bonding interactions and the formation of the two-dimensional arrangement. [Symmetry codes: (i) -x + 2, y - 1/2, -z - 1/2; (ii) -x + 1, y - 1/2, -z + 1/2.]

Crystal data

[Ni(C16H10N3O3)2(C5H5N)2]F(000) = 1656
Mr = 801.45Dx = 1.423 Mg m3
Monoclinic, P21/cMelting point: 473 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.719 (2) ÅCell parameters from 217 reflections
b = 18.885 (4) Åθ = 1.0–27.5°
c = 16.922 (3) ŵ = 0.58 mm1
β = 93.04 (3)°T = 295 K
V = 3740.0 (13) Å3Block, red
Z = 40.37 × 0.18 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer6566 independent reflections
Radiation source: fine-focus sealed tube4859 reflections with I > 2σ(I)
graphiteRint = 0.076
[var phi] and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −13→13
Tmin = 0.814, Tmax = 0.918k = −22→22
64998 measured reflectionsl = −20→20

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0357P)2 + 1.6025P] where P = (Fo2 + 2Fc2)/3
6566 reflections(Δ/σ)max < 0.001
514 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

Experimental. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)5.9841 (0.0107) x + 0.5948 (0.0176) y + 14.0605 (0.0119) z = 4.0378 (0.0057)* 0.0370 (0.0010) N1 * -0.0652 (0.0015) N2 * 0.0496 (0.0015) C1 * -0.0087 (0.0015) C2 * -0.0127 (0.0010) O1Rms deviation of fitted atoms = 0.0408- 0.4462 (0.0069) x + 8.8584 (0.0115) y + 14.9440 (0.0093) z = 1.2966 (0.0053)Angle to previous plane (with approximate e.s.d.) = 41.11 (0.07)* 0.0666 (0.0009) O1 * -0.0633 (0.0009) N1 * 0.0616 (0.0008) O4 * -0.0623 (0.0009) N8 * -0.0026 (0.0008) Ni1Rms deviation of fitted atoms = 0.05686.2807 (0.0104) x - 6.1779 (0.0201) y + 12.6704 (0.0108) z = 5.5919 (0.0111)Angle to previous plane (with approximate e.s.d.) = 59.14 (0.06)* -0.0118 (0.0011) O4 * 0.0423 (0.0016) C18 * -0.0623 (0.0015) C17 * 0.0507 (0.0015) N5 * -0.0189 (0.0010) N4Rms deviation of fitted atoms = 0.0418- 0.0859 (0.0070) x + 16.1355 (0.0106) y - 8.7731 (0.0106) z = 1.4081 (0.0053)Angle to previous plane (with approximate e.s.d.) = 46.54 (0.09)* 0.0058 (0.0009) O4 * 0.0056 (0.0010) N4 * 0.0063 (0.0009) O1 * 0.0060 (0.0009) N7 * -0.0236 (0.0008) Ni1Rms deviation of fitted atoms = 0.01186.5874 (0.0126) x + 14.2991 (0.0164) y - 6.1291 (0.0186) z = 6.0049 (0.0088)Angle to previous plane (with approximate e.s.d.) = 35.34 (0.09)* 0.0044 (0.0017) N7 * -0.0069 (0.0020) C33 * 0.0029 (0.0023) C34 * 0.0033 (0.0025) C35 * -0.0056 (0.0023) C36 * 0.0019 (0.0019) C37Rms deviation of fitted atoms = 0.00456.8092 (0.0117) x - 4.2913 (0.0191) y - 13.7284 (0.0134) z = 3.6963 (0.0099)Angle to previous plane (with approximate e.s.d.) = 65.50 (0.09)* 0.0087 (0.0016) N8 * -0.0004 (0.0019) C38 * -0.0074 (0.0021) C39 * 0.0071 (0.0020) C40 * 0.0011 (0.0019) C41 * -0.0092 (0.0018) C42Rms deviation of fitted atoms = 0.00677.6103 (0.0099) x - 1.0403 (0.0194) y + 12.2331 (0.0135) z = 7.5132 (0.0060)Angle to previous plane (with approximate e.s.d.) = 78.29 (0.07)* -0.0081 (0.0017) C27 * 0.0104 (0.0018) C28 * -0.0020 (0.0018) C29 * -0.0088 (0.0018) C30 * 0.0109 (0.0019) C31 * -0.0025 (0.0019) C32Rms deviation of fitted atoms = 0.00796.0882 (0.0095) x - 3.0287 (0.0105) y + 13.7154 (0.0112) z = 6.1985 (0.0098)Angle to previous plane (with approximate e.s.d.) = 10.66 (0.13)* 0.0072 (0.0020) C17 * -0.1226 (0.0020) C18 * 0.0188 (0.0022) C19 * 0.0637 (0.0024) C20 * 0.0353 (0.0026) C21 * -0.0368 (0.0028) C22 * -0.0666 (0.0033) C23 * -0.0092 (0.0031) C24 * 0.0452 (0.0026) C25 * 0.0652 (0.0024) C26Rms deviation of fitted atoms = 0.05746.0989 (0.0089) x - 1.3127 (0.0101) y + 13.9139 (0.0107) z = 3.6881 (0.0050)Angle to previous plane (with approximate e.s.d.) = 5.25 (0.11)* -0.0019 (0.0019) C1 * 0.0685 (0.0019) C2 * -0.0202 (0.0021) C3 * -0.0339 (0.0022) C4 * -0.0136 (0.0024) C5 * 0.0221 (0.0025) C6 * 0.0381 (0.0028) C7 * -0.0039 (0.0027) C8 * -0.0255 (0.0024) C9 * -0.0297 (0.0023) C10Rms deviation of fitted atoms = 0.03157.6507 (0.0101) x - 0.7993 (0.0215) y + 12.1938 (0.0139) z = 4.9408 (0.0114)Angle to previous plane (with approximate e.s.d.) = 9.47 (0.13)* 0.0100 (0.0017) C11 * -0.0050 (0.0019) C12 * -0.0055 (0.0021) C13 * 0.0110 (0.0019) C14 * -0.0058 (0.0018) C15 * -0.0048 (0.0018) C16Rms deviation of fitted atoms = 0.0075
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
Ni10.73654 (2)0.112500 (16)0.041889 (18)0.03358 (10)
N10.71063 (15)0.21142 (10)−0.02158 (11)0.0336 (4)
N20.63714 (16)0.25763 (10)0.00047 (11)0.0370 (5)
N31.0357 (2)0.33257 (17)−0.21680 (16)0.0701 (8)
N40.75644 (16)0.17270 (10)0.14908 (11)0.0379 (5)
N50.81962 (17)0.22968 (11)0.15104 (12)0.0401 (5)
N60.4055 (2)0.16963 (14)0.36697 (13)0.0531 (6)
N70.73012 (17)0.05551 (10)−0.06623 (12)0.0406 (5)
N80.74895 (17)0.01201 (10)0.09784 (12)0.0386 (5)
C10.54975 (19)0.23983 (13)0.04658 (13)0.0358 (5)
C20.51196 (19)0.16895 (14)0.06152 (14)0.0373 (6)
C30.4060 (2)0.16159 (16)0.10089 (15)0.0471 (6)
H30.37510.11660.10670.056*
C40.3506 (2)0.21795 (17)0.12949 (16)0.0543 (8)
H40.28440.21030.15610.065*
C50.3901 (2)0.28914 (16)0.12038 (15)0.0480 (7)
C60.3342 (3)0.3474 (2)0.15296 (18)0.0678 (9)
H60.26960.33980.18150.081*
C70.3728 (3)0.4148 (2)0.1435 (2)0.0803 (11)
H70.33560.45270.16620.096*
C80.4683 (3)0.42665 (18)0.0997 (2)0.0732 (10)
H80.49370.47270.09200.088*
C90.5259 (3)0.37042 (15)0.06765 (18)0.0577 (8)
H90.59040.37910.03940.069*
C100.4883 (2)0.30047 (14)0.07722 (14)0.0426 (6)
C110.78929 (19)0.24392 (12)−0.07322 (13)0.0340 (5)
C120.8024 (2)0.31680 (14)−0.07792 (16)0.0482 (7)
H120.75740.3463−0.04850.058*
C130.8815 (3)0.34579 (15)−0.12567 (17)0.0575 (8)
H130.89000.3947−0.12870.069*
C140.9481 (2)0.30173 (15)−0.16898 (15)0.0465 (7)
C150.9355 (2)0.22981 (14)−0.16720 (15)0.0451 (6)
H150.97980.2009−0.19780.054*
C160.8561 (2)0.20082 (13)−0.11915 (15)0.0415 (6)
H160.84700.1519−0.11740.050*
C170.9075 (2)0.23637 (13)0.10183 (14)0.0413 (6)
C180.9558 (2)0.17932 (14)0.05833 (15)0.0425 (6)
C191.0637 (2)0.19248 (16)0.02366 (17)0.0532 (7)
H191.10290.15480.00240.064*
C201.1091 (2)0.25816 (18)0.02127 (18)0.0605 (8)
H201.17710.2647−0.00370.073*
C211.0559 (2)0.31780 (17)0.05598 (17)0.0571 (8)
C221.0988 (3)0.3870 (2)0.0470 (2)0.0810 (11)
H221.16300.39410.01800.097*
C231.0472 (4)0.4438 (2)0.0802 (3)0.0974 (14)
H231.07560.48920.07340.117*
C240.9519 (4)0.43321 (19)0.1244 (3)0.0902 (12)
H240.91800.47170.14810.108*
C250.9069 (3)0.36590 (16)0.13346 (19)0.0663 (9)
H250.84240.35980.16240.080*
C260.9579 (2)0.30722 (15)0.09933 (16)0.0495 (7)
C270.6742 (2)0.17444 (13)0.20889 (13)0.0376 (6)
C280.6336 (2)0.23743 (13)0.24103 (15)0.0418 (6)
H280.66500.28050.22680.050*
C290.5478 (2)0.23611 (14)0.29330 (15)0.0449 (6)
H290.52020.27810.31380.054*
C300.5028 (2)0.17145 (14)0.31523 (14)0.0416 (6)
C310.5433 (2)0.10847 (14)0.28627 (14)0.0463 (6)
H310.51400.06540.30260.056*
C320.6281 (2)0.11035 (14)0.23263 (15)0.0466 (6)
H320.65470.06820.21200.056*
C330.6487 (2)0.06812 (15)−0.12249 (16)0.0511 (7)
H330.58970.0989−0.11150.061*
C340.6486 (3)0.03716 (19)−0.19646 (19)0.0736 (10)
H340.59130.0475−0.23490.088*
C350.7351 (3)−0.0094 (2)−0.2122 (2)0.0834 (12)
H350.7370−0.0310−0.26150.100*
C360.8178 (3)−0.02345 (18)−0.1546 (2)0.0731 (10)
H360.8763−0.0552−0.16390.088*
C370.8135 (2)0.00968 (14)−0.08311 (17)0.0519 (7)
H370.87070.0002−0.04430.062*
C380.8368 (2)−0.00533 (14)0.14751 (16)0.0485 (7)
H380.88930.02970.16270.058*
C390.8535 (3)−0.07288 (16)0.17741 (18)0.0595 (8)
H390.9154−0.08280.21230.071*
C400.7765 (3)−0.12535 (15)0.15457 (18)0.0580 (8)
H400.7864−0.17150.17290.070*
C410.6855 (2)−0.10789 (14)0.10441 (17)0.0512 (7)
H410.6321−0.14210.08840.061*
C420.6738 (2)−0.03930 (13)0.07789 (16)0.0444 (6)
H420.6107−0.02800.04460.053*
O10.56484 (13)0.11301 (9)0.04110 (10)0.0399 (4)
O21.0358 (3)0.39692 (16)−0.22459 (19)0.1256 (12)
O31.1043 (2)0.29343 (15)−0.24720 (15)0.0888 (8)
O40.90854 (14)0.11845 (9)0.04779 (10)0.0449 (4)
O50.3680 (2)0.11152 (12)0.38569 (14)0.0799 (7)
O60.36631 (19)0.22562 (12)0.38958 (14)0.0758 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.03349 (16)0.03100 (16)0.03668 (17)−0.00179 (13)0.00593 (12)−0.00190 (14)
N10.0334 (10)0.0355 (11)0.0326 (11)−0.0007 (9)0.0084 (8)−0.0021 (9)
N20.0360 (11)0.0394 (12)0.0358 (11)0.0018 (9)0.0035 (9)−0.0009 (9)
N30.0730 (18)0.082 (2)0.0574 (16)−0.0254 (16)0.0229 (14)0.0154 (15)
N40.0411 (11)0.0361 (11)0.0367 (11)−0.0049 (9)0.0021 (9)0.0001 (9)
N50.0453 (12)0.0389 (12)0.0354 (11)−0.0060 (10)−0.0040 (9)0.0009 (9)
N60.0605 (15)0.0575 (16)0.0422 (13)0.0017 (13)0.0103 (11)−0.0041 (12)
N70.0450 (12)0.0345 (11)0.0432 (12)−0.0056 (9)0.0103 (10)−0.0051 (10)
N80.0407 (11)0.0347 (11)0.0410 (12)0.0008 (9)0.0063 (9)−0.0002 (9)
C10.0346 (13)0.0434 (14)0.0299 (13)0.0023 (11)0.0045 (10)−0.0015 (11)
C20.0308 (12)0.0500 (15)0.0311 (13)0.0022 (11)0.0005 (10)−0.0028 (11)
C30.0313 (13)0.0617 (18)0.0488 (16)−0.0056 (12)0.0077 (11)0.0017 (14)
C40.0323 (14)0.089 (2)0.0428 (16)0.0034 (14)0.0072 (12)−0.0034 (15)
C50.0369 (14)0.0677 (19)0.0392 (15)0.0134 (13)0.0006 (11)−0.0089 (13)
C60.0507 (18)0.093 (3)0.060 (2)0.0191 (18)0.0077 (15)−0.0226 (19)
C70.074 (2)0.084 (3)0.083 (3)0.032 (2)0.004 (2)−0.036 (2)
C80.080 (2)0.057 (2)0.083 (2)0.0170 (17)0.0030 (19)−0.0207 (18)
C90.0619 (18)0.0523 (18)0.0594 (19)0.0119 (14)0.0090 (15)−0.0092 (14)
C100.0426 (14)0.0510 (16)0.0340 (14)0.0106 (12)−0.0011 (11)−0.0044 (12)
C110.0357 (13)0.0371 (13)0.0291 (12)−0.0040 (10)0.0005 (10)0.0022 (10)
C120.0582 (17)0.0404 (15)0.0473 (16)−0.0031 (12)0.0155 (13)−0.0014 (12)
C130.072 (2)0.0411 (16)0.0603 (19)−0.0136 (14)0.0173 (15)0.0090 (14)
C140.0456 (15)0.0587 (18)0.0358 (14)−0.0105 (13)0.0074 (12)0.0098 (13)
C150.0435 (15)0.0518 (17)0.0413 (15)0.0018 (12)0.0131 (12)0.0049 (12)
C160.0430 (14)0.0362 (14)0.0464 (15)−0.0019 (11)0.0128 (12)0.0032 (12)
C170.0412 (14)0.0465 (15)0.0353 (14)−0.0087 (12)−0.0053 (11)0.0041 (12)
C180.0353 (13)0.0508 (17)0.0409 (14)−0.0035 (12)−0.0032 (11)0.0084 (12)
C190.0363 (14)0.0658 (19)0.0575 (18)−0.0043 (13)0.0024 (13)0.0042 (15)
C200.0383 (15)0.087 (2)0.0555 (18)−0.0191 (16)−0.0039 (13)0.0154 (17)
C210.0522 (17)0.066 (2)0.0515 (17)−0.0233 (15)−0.0131 (14)0.0154 (15)
C220.074 (2)0.080 (3)0.087 (3)−0.040 (2)−0.0172 (19)0.027 (2)
C230.117 (4)0.056 (2)0.116 (4)−0.038 (2)−0.020 (3)0.020 (2)
C240.114 (3)0.050 (2)0.104 (3)−0.021 (2)−0.008 (3)−0.004 (2)
C250.081 (2)0.0481 (18)0.069 (2)−0.0153 (16)−0.0033 (17)−0.0007 (15)
C260.0538 (16)0.0490 (17)0.0442 (16)−0.0140 (13)−0.0131 (13)0.0053 (13)
C270.0435 (14)0.0403 (14)0.0287 (12)−0.0014 (11)−0.0010 (10)−0.0031 (11)
C280.0486 (15)0.0366 (14)0.0399 (15)−0.0065 (11)0.0010 (12)−0.0024 (11)
C290.0555 (16)0.0387 (15)0.0405 (15)0.0013 (12)0.0021 (12)−0.0106 (12)
C300.0461 (14)0.0480 (16)0.0310 (13)0.0009 (12)0.0032 (11)−0.0040 (12)
C310.0629 (17)0.0366 (14)0.0404 (14)−0.0010 (13)0.0132 (12)0.0038 (12)
C320.0624 (17)0.0366 (14)0.0420 (14)0.0016 (13)0.0129 (12)−0.0015 (12)
C330.0589 (17)0.0480 (17)0.0466 (16)−0.0088 (13)0.0054 (14)−0.0072 (13)
C340.080 (2)0.090 (3)0.0504 (19)−0.027 (2)−0.0005 (17)−0.0147 (18)
C350.099 (3)0.091 (3)0.064 (2)−0.031 (2)0.037 (2)−0.042 (2)
C360.072 (2)0.069 (2)0.082 (2)−0.0109 (18)0.037 (2)−0.032 (2)
C370.0527 (16)0.0437 (16)0.0614 (18)−0.0034 (13)0.0233 (14)−0.0109 (14)
C380.0496 (16)0.0451 (16)0.0505 (16)0.0002 (12)−0.0006 (13)−0.0016 (13)
C390.0621 (19)0.0571 (19)0.0584 (19)0.0098 (15)−0.0056 (15)0.0089 (15)
C400.074 (2)0.0377 (16)0.0638 (19)0.0050 (14)0.0153 (16)0.0099 (14)
C410.0599 (17)0.0389 (15)0.0557 (17)−0.0084 (13)0.0102 (14)0.0021 (13)
C420.0449 (15)0.0391 (15)0.0495 (16)−0.0038 (12)0.0060 (12)0.0010 (12)
O10.0348 (9)0.0402 (9)0.0453 (10)−0.0050 (8)0.0083 (7)−0.0032 (8)
O20.157 (3)0.083 (2)0.145 (3)−0.0318 (19)0.088 (2)0.0334 (19)
O30.0725 (16)0.114 (2)0.0840 (18)−0.0154 (15)0.0420 (14)0.0119 (16)
O40.0380 (9)0.0412 (10)0.0561 (11)−0.0026 (8)0.0067 (8)−0.0015 (9)
O50.0960 (17)0.0644 (15)0.0839 (16)−0.0114 (13)0.0483 (13)−0.0033 (13)
O60.0788 (15)0.0641 (14)0.0879 (17)0.0151 (12)0.0367 (13)−0.0108 (12)

Geometric parameters (Å, °)

Ni1—N12.168 (2)C16—H160.9300
Ni1—N42.143 (2)C17—C181.438 (4)
Ni1—N72.121 (2)C17—C261.464 (3)
Ni1—N82.122 (2)C18—O41.284 (3)
Ni1—O12.0116 (16)C18—C191.443 (3)
Ni1—O42.0161 (17)C19—C201.351 (4)
N1—N21.295 (3)C19—H190.9300
N1—C111.441 (3)C20—C211.429 (4)
N2—C11.362 (3)C20—H200.9300
N3—O21.222 (4)C21—C261.409 (4)
N3—O31.225 (4)C22—C231.366 (5)
N3—C141.462 (3)C22—C211.412 (4)
N4—N51.306 (3)C22—H220.9300
N4—C271.434 (3)C23—C241.390 (6)
N5—C171.364 (3)C23—H230.9300
N6—O51.230 (3)C24—C251.388 (4)
N6—C301.474 (3)C24—H240.9300
N7—C331.333 (3)C25—C261.398 (4)
N7—C371.348 (3)C25—H250.9300
N8—C381.335 (3)C27—C321.394 (3)
N8—C421.341 (3)C27—C281.402 (3)
C1—C21.437 (3)C28—C291.374 (3)
C1—C101.462 (3)C28—H280.9300
C2—O11.281 (3)C29—C301.389 (3)
C2—C31.447 (3)C29—H290.9300
C3—C41.350 (4)C30—C311.380 (3)
C3—H30.9300C31—C321.381 (3)
C4—C51.433 (4)C31—H310.9300
C4—H40.9300C32—H320.9300
C5—C61.409 (4)C33—C341.381 (4)
C5—C101.412 (4)C33—H330.9300
C6—C71.363 (5)C34—C351.379 (5)
C6—H60.9300C34—H340.9300
C7—H70.9300C35—C361.363 (5)
C8—C91.384 (4)C35—H350.9300
C8—C71.393 (5)C36—C371.365 (4)
C8—H80.9300C36—H360.9300
C9—C101.405 (4)C37—H370.9300
C9—H90.9300C38—C391.382 (4)
C11—C121.388 (3)C38—H380.9300
C11—C161.394 (3)C39—C401.381 (4)
C12—C131.375 (4)C39—H390.9300
C12—H120.9300C40—C411.368 (4)
C13—C141.378 (4)C40—H400.9300
C13—H130.9300C41—C421.375 (4)
C14—C151.367 (4)C41—H410.9300
C15—C161.382 (3)C42—H420.9300
C15—H150.9300O6—N61.222 (3)
N1—N2—C1122.0 (2)C8—C7—H7120.2
N2—C1—C2125.4 (2)C8—C9—C10120.9 (3)
N2—C1—C10114.1 (2)C8—C9—H9119.5
N2—N1—C11110.14 (18)C10—C9—H9119.5
N2—N1—Ni1121.05 (14)C9—C10—C5118.1 (2)
N4—Ni1—N188.18 (7)C9—C10—C1122.2 (2)
N4—N5—C17120.4 (2)C5—C10—C1119.7 (2)
N5—N4—C27111.37 (19)C12—C11—C16118.7 (2)
N5—N4—Ni1119.66 (15)C12—C11—N1122.3 (2)
N5—C17—C18125.0 (2)C16—C11—N1119.0 (2)
N5—C17—C26114.9 (2)C13—C12—C11120.6 (3)
N7—Ni1—N190.70 (8)C13—C12—H12119.7
N7—Ni1—N4175.45 (7)C11—C12—H12119.7
N7—Ni1—N885.96 (8)C12—C13—C14119.4 (3)
N7—C37—C36122.9 (3)C12—C13—H13120.3
N7—C37—H37118.5C14—C13—H13120.3
N7—C33—C34122.5 (3)C15—C14—C13121.6 (2)
N7—C33—H33118.7C15—C14—N3119.2 (3)
N8—C42—C41123.1 (3)C13—C14—N3119.2 (3)
N8—C42—H42118.5C14—C15—C16118.9 (2)
N8—C38—C39123.1 (3)C14—C15—H15120.5
N8—C38—H38118.5C16—C15—H15120.5
N8—Ni1—N1174.80 (8)C15—C16—C11120.8 (2)
N8—Ni1—N495.45 (8)C15—C16—H16119.6
O1—Ni1—N493.84 (7)C11—C16—H16119.6
O1—Ni1—O4175.75 (7)C18—C17—C26120.0 (2)
O1—Ni1—N790.40 (8)C17—C18—C19117.1 (2)
O1—Ni1—N892.99 (7)C20—C19—C18121.7 (3)
O1—Ni1—N183.04 (7)C20—C19—H19119.2
O1—C2—C1124.2 (2)C18—C19—H19119.2
O1—C2—C3119.0 (2)C19—C20—C21122.0 (3)
O2—N3—O3123.4 (3)C19—C20—H20119.0
O2—N3—C14117.4 (3)C21—C20—H20119.0
O3—N3—C14119.2 (3)C26—C21—C22119.5 (3)
O4—Ni1—N482.23 (8)C26—C21—C20119.2 (3)
O4—Ni1—N793.47 (8)C22—C21—C20121.3 (3)
O4—Ni1—N889.03 (7)C25—C26—C21118.7 (3)
O4—Ni1—N195.16 (7)C25—C26—C17122.0 (3)
O4—C18—C17124.3 (2)C21—C26—C17119.1 (3)
O4—C18—C19118.6 (2)C32—C27—C28118.7 (2)
O5—N6—C30118.2 (2)C32—C27—N4118.0 (2)
O6—N6—O5123.1 (2)C28—C27—N4123.2 (2)
O6—N6—C30118.8 (2)C29—C28—C27120.6 (2)
C11—N1—Ni1126.17 (14)C29—C28—H28119.7
C27—N4—Ni1124.23 (15)C27—C28—H28119.7
C9—C8—C7120.5 (3)C28—C29—C30119.3 (2)
C9—C8—H8119.7C28—C29—H29120.4
C7—C8—H8119.7C30—C29—H29120.4
C23—C22—C21120.9 (4)C31—C30—C29121.3 (2)
C23—C22—H22119.5C31—C30—N6118.8 (2)
C21—C22—H22119.5C29—C30—N6119.7 (2)
C22—C23—C24119.7 (3)C30—C31—C32119.0 (2)
C22—C23—H23120.2C30—C31—H31120.5
C24—C23—H23120.2C32—C31—H31120.5
C25—C24—C23120.8 (4)C31—C32—C27121.0 (2)
C25—C24—H24119.6C31—C32—H32119.5
C23—C24—H24119.6C27—C32—H32119.5
C24—C25—C26120.4 (3)C34—C33—H33118.7
C24—C25—H25119.8C35—C34—C33118.6 (3)
C26—C25—H25119.8C35—C34—H34120.7
C33—N7—C37117.6 (2)C33—C34—H34120.7
C33—N7—Ni1121.11 (17)C36—C35—C34119.2 (3)
C37—N7—Ni1121.06 (19)C36—C35—H35120.4
C38—N8—C42117.1 (2)C34—C35—H35120.4
C38—N8—Ni1122.17 (17)C35—C36—C37119.1 (3)
C42—N8—Ni1120.36 (17)C35—C36—H36120.5
C2—C1—C10120.4 (2)C37—C36—H36120.5
C1—C2—C3116.8 (2)C36—C37—H37118.5
C4—C3—C2122.0 (3)C39—C38—H38118.5
C4—C3—H3119.0C40—C39—C38118.8 (3)
C2—C3—H3119.0C40—C39—H39120.6
C3—C4—C5122.5 (2)C38—C39—H39120.6
C3—C4—H4118.7C41—C40—C39118.5 (3)
C5—C4—H4118.7C41—C40—H40120.8
C6—C5—C10119.5 (3)C39—C40—H40120.8
C6—C5—C4122.1 (3)C40—C41—C42119.4 (3)
C10—C5—C4118.3 (2)C40—C41—H41120.3
C7—C6—C5121.3 (3)C42—C41—H41120.3
C7—C6—H6119.3C41—C42—H42118.5
C5—C6—H6119.3C2—O1—Ni1120.00 (14)
C6—C7—C8119.5 (3)C18—O4—Ni1118.64 (15)
C6—C7—H7120.2
C21—C22—C23—C240.8 (6)O2—N3—C14—C13−9.6 (4)
C22—C23—C24—C25−1.6 (6)O3—N3—C14—C13170.8 (3)
C23—C24—C25—C261.1 (6)C13—C14—C15—C16−1.7 (4)
O1—Ni1—N1—N243.27 (17)N3—C14—C15—C16177.1 (2)
O4—Ni1—N1—N2−132.86 (17)C14—C15—C16—C110.1 (4)
N7—Ni1—N1—N2133.59 (17)C12—C11—C16—C151.4 (4)
N4—Ni1—N1—N2−50.82 (17)N1—C11—C16—C15−177.6 (2)
O1—Ni1—N1—C11−156.98 (18)N4—N5—C17—C18−14.8 (4)
O4—Ni1—N1—C1126.89 (18)N4—N5—C17—C26169.2 (2)
N7—Ni1—N1—C11−66.66 (18)N5—C17—C18—O414.6 (4)
N4—Ni1—N1—C11108.92 (18)C26—C17—C18—O4−169.7 (2)
C11—N1—N2—C1176.8 (2)N5—C17—C18—C19−166.3 (2)
Ni1—N1—N2—C1−20.5 (3)C26—C17—C18—C199.4 (3)
O1—Ni1—N4—N5−127.58 (17)O4—C18—C19—C20169.1 (3)
O4—Ni1—N4—N550.77 (17)C17—C18—C19—C20−10.0 (4)
N8—Ni1—N4—N5139.04 (17)C18—C19—C20—C212.9 (4)
N1—Ni1—N4—N5−44.68 (17)C23—C22—C21—C260.5 (5)
O1—Ni1—N4—C2725.88 (19)C23—C22—C21—C20179.8 (3)
O4—Ni1—N4—C27−155.77 (19)C19—C20—C21—C265.0 (4)
N8—Ni1—N4—C27−67.50 (19)C19—C20—C21—C22−174.3 (3)
N1—Ni1—N4—C27108.78 (18)C24—C25—C26—C210.3 (5)
C27—N4—N5—C17176.1 (2)C24—C25—C26—C17−174.7 (3)
Ni1—N4—N5—C17−27.2 (3)C22—C21—C26—C25−1.1 (4)
O1—Ni1—N7—C3336.6 (2)C20—C21—C26—C25179.6 (3)
O4—Ni1—N7—C33−141.64 (19)C22—C21—C26—C17174.0 (3)
N8—Ni1—N7—C33129.6 (2)C20—C21—C26—C17−5.3 (4)
N1—Ni1—N7—C33−46.4 (2)N5—C17—C26—C25−10.9 (4)
O1—Ni1—N7—C37−149.05 (19)C18—C17—C26—C25172.9 (3)
O4—Ni1—N7—C3732.70 (19)N5—C17—C26—C21174.1 (2)
N8—Ni1—N7—C37−56.08 (19)C18—C17—C26—C21−2.0 (4)
N1—Ni1—N7—C37127.91 (19)N5—N4—C27—C32−158.6 (2)
O1—Ni1—N8—C38−147.84 (19)Ni1—N4—C27—C3246.0 (3)
O4—Ni1—N8—C3828.4 (2)N5—N4—C27—C2825.2 (3)
N7—Ni1—N8—C38122.0 (2)Ni1—N4—C27—C28−130.2 (2)
N4—Ni1—N8—C38−53.7 (2)C32—C27—C28—C29−1.7 (4)
O1—Ni1—N8—C4239.14 (19)N4—C27—C28—C29174.5 (2)
O4—Ni1—N8—C42−144.60 (19)C27—C28—C29—C301.2 (4)
N7—Ni1—N8—C42−51.05 (19)C28—C29—C30—C310.7 (4)
N4—Ni1—N8—C42133.29 (18)C28—C29—C30—N6−175.9 (2)
N1—N2—C1—C2−14.7 (4)O6—N6—C30—C31−176.6 (2)
N1—N2—C1—C10169.5 (2)O5—N6—C30—C313.7 (4)
N2—C1—C2—O19.0 (4)O6—N6—C30—C290.0 (4)
C10—C1—C2—O1−175.5 (2)O5—N6—C30—C29−179.6 (3)
N2—C1—C2—C3−169.8 (2)C29—C30—C31—C32−1.9 (4)
C10—C1—C2—C35.7 (3)N6—C30—C31—C32174.7 (2)
O1—C2—C3—C4174.7 (2)C30—C31—C32—C271.3 (4)
C1—C2—C3—C4−6.4 (4)C28—C27—C32—C310.5 (4)
C2—C3—C4—C52.4 (4)N4—C27—C32—C31−175.9 (2)
C3—C4—C5—C6−177.6 (3)C37—N7—C33—C34−1.2 (4)
C3—C4—C5—C102.4 (4)Ni1—N7—C33—C34173.4 (2)
C10—C5—C6—C70.2 (4)N7—C33—C34—C351.0 (5)
C4—C5—C6—C7−179.9 (3)C33—C34—C35—C360.0 (5)
C5—C6—C7—C81.1 (5)C34—C35—C36—C37−0.8 (5)
C9—C8—C7—C6−1.7 (5)C33—N7—C37—C360.3 (4)
C7—C8—C9—C101.1 (5)Ni1—N7—C37—C36−174.2 (2)
C8—C9—C10—C50.1 (4)C35—C36—C37—N70.7 (5)
C8—C9—C10—C1−177.7 (3)C42—N8—C38—C391.0 (4)
C6—C5—C10—C9−0.8 (4)Ni1—N8—C38—C39−172.3 (2)
C4—C5—C10—C9179.3 (2)N8—C38—C39—C400.6 (4)
C6—C5—C10—C1177.1 (2)C38—C39—C40—C41−1.3 (4)
C4—C5—C10—C1−2.9 (4)C39—C40—C41—C420.5 (4)
N2—C1—C10—C9−7.5 (4)C38—N8—C42—C41−1.8 (4)
C2—C1—C10—C9176.5 (2)Ni1—N8—C42—C41171.5 (2)
N2—C1—C10—C5174.8 (2)C40—C41—C42—N81.1 (4)
C2—C1—C10—C5−1.2 (3)C1—C2—O1—Ni134.0 (3)
N2—N1—C11—C1217.2 (3)C3—C2—O1—Ni1−147.22 (18)
Ni1—N1—C11—C12−144.4 (2)N7—Ni1—O1—C2−138.84 (17)
N2—N1—C11—C16−163.9 (2)N8—Ni1—O1—C2135.18 (17)
Ni1—N1—C11—C1634.5 (3)N4—Ni1—O1—C239.51 (18)
C16—C11—C12—C13−1.4 (4)N1—Ni1—O1—C2−48.18 (17)
N1—C11—C12—C13177.5 (2)C17—C18—O4—Ni130.8 (3)
C11—C12—C13—C14−0.1 (4)C19—C18—O4—Ni1−148.24 (19)
C12—C13—C14—C151.7 (4)N7—Ni1—O4—C18128.08 (18)
C12—C13—C14—N3−177.1 (3)N8—Ni1—O4—C18−146.03 (18)
O2—N3—C14—C15171.5 (3)N4—Ni1—O4—C18−50.39 (18)
O3—N3—C14—C15−8.0 (4)N1—Ni1—O4—C1837.06 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C36—H36···O2i0.932.383.124 (5)137
C41—H41···O6ii0.932.533.205 (4)130

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

Footnotes

1Dedicated to the memory of Professor Jairo Bordinhão.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2206).

References

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