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

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Bis[μ2-N′-acetyl-2-hy­droxy-6-oxido­benzohydrazidato(3−)]octa­pyridine­trinickel(II)

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: lidacheng62@lcu.edu.cn

(Received 19 May 2009; accepted 29 May 2009; online 6 June 2009)

The title trinuclear complex, [Ni3(C9H7N2O4)2(C5H5N)8], possesses a crystallographically imposed center of symmetry occupied by one NiII ion. Each of the three NiII ions is coordinated by two O and four N atoms, respectively, in a distorted octa­hedral geometry. In the crystal, weak inter­molecular C—H⋯π inter­actions link the mol­ecules into ribbons propagating in the [100] direction.

Related literature

For applications of N-acetyl­salicylhydrazide complexes, see: John et al. (2004[John, R. P., Lee, K. J. & Lah, M. S. (2004). Chem. Commun. pp. 2660-2661.]); Lin et al. (2002[Lin, S., Liu, S. X. & Lin, B. Z. (2002). Inorg. Chim. Acta, 328, 69-73.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni3(C9H7N2O4)2(C5H5N)8]

  • Mr = 1223.26

  • Monoclinic, P 21 /n

  • a = 9.9349 (18) Å

  • b = 18.230 (3) Å

  • c = 16.262 (2) Å

  • β = 96.663 (2)°

  • V = 2925.3 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.02 mm−1

  • T = 298 K

  • 0.53 × 0.45 × 0.44 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.614, Tmax = 0.663

  • 14103 measured reflections

  • 5138 independent reflections

  • 3047 reflections with I > 2σ(I)

  • Rint = 0.146

Refinement
  • R[F2 > 2σ(F2)] = 0.075

  • wR(F2) = 0.210

  • S = 0.97

  • 5138 reflections

  • 368 parameters

  • 1098 restraints

  • H-atom parameters constrained

  • Δρmax = 1.32 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C27—H27⋯Cgi 0.93 2.52 3.428 (4) 166
Symmetry code: (i) x+1, y, z. Cg is the centroid of the C2–C7 ring.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In recent years, a large number of N-acetylsalicylhydrazide complexes have been prepared and studied due to their potential applications in chemically modified (Lin et al., 2002) and anion-selective separation agents (John et al., 2004). However, structures of nickel(II) complexes with N-acetyl-6-hydroxysalicylhydrzaide were not reported. So we have synthesized the title compound, which has been characterized by X-ray diffraction and elemental analysis.

The title complex (Fig. 1) contains three nickel(II) centers having distorted octahedral coordination environment, two ligand molecules and eight pyridine molecules. The triple-deprotonated N-acetyl-6-hydroxysalicylhydrzaide ligands bridge metal ions via hydrazide N—N group forming trinuclear nickel complex. In the crystal, the complex molecules are linked into ribbons via intermolecular C—H···π weak interactions (Table 1, Fig. 2).

Related literature top

For applications of N-acetylsalicylhydrazide complexes, see: John et al. (2004); Lin et al. (2002).

Experimental top

A solution of Ni(OAc)2.4H2O (0.4 mmol, 0.0996 g) in dimethylformamide (10 ml) was add to N-acetyl-(6-hydroxysalicylhydrzaide) (0.2 mmol, 0.042 g) in pyridine (10 ml). A reddish solution was obtained after refluxing for 3 h. After the solution had been stanging for two weeks, red block crystals suitable for X-ray diffraction appear.(m.p. >400 K). Elemental analysis calculated for C58H54N12O8Ni3: C 56.95, H 4.45, N 13.74%; found: C 56.92, H 4.44, N 13.76%.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms with C—H 0.93 (pyridine, benzene) or 0.97 (methylene) Å [Uiso(H) = 1.2Ueq(C)], and O—H 0.82 Å (hydroxyl) [Uiso(H) = 1.5Ueq(O)].

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing 40% probability displacement ellipsoids and the atomic numbering [symmetry code: (A) -x, -y, 2-z]. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A portion of the crystal packing showing one-dimensional ribbons. Intermolecular C—H···π interactions are shown as dashed lines. Most of H atoms are omitted.
Bis[µ2-N'-acetyl-2-hydroxy-6- oxidobenzohydrazidato(3-)]octapyridinetrinickel(II) top
Crystal data top
[Ni3(C9H7N2O4)2(C5H5N)8]F(000) = 1268
Mr = 1223.26Dx = 1.389 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.9349 (18) ÅCell parameters from 4241 reflections
b = 18.230 (3) Åθ = 2.2–26.2°
c = 16.262 (2) ŵ = 1.02 mm1
β = 96.663 (2)°T = 298 K
V = 2925.3 (8) Å3Block, red
Z = 20.53 × 0.45 × 0.44 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5138 independent reflections
Radiation source: fine-focus sealed tube3047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.146
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.614, Tmax = 0.663k = 1621
14103 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0999P)2]
where P = (Fo2 + 2Fc2)/3
5138 reflections(Δ/σ)max < 0.001
368 parametersΔρmax = 1.32 e Å3
1098 restraintsΔρmin = 0.58 e Å3
Crystal data top
[Ni3(C9H7N2O4)2(C5H5N)8]V = 2925.3 (8) Å3
Mr = 1223.26Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.9349 (18) ŵ = 1.02 mm1
b = 18.230 (3) ÅT = 298 K
c = 16.262 (2) Å0.53 × 0.45 × 0.44 mm
β = 96.663 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5138 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3047 reflections with I > 2σ(I)
Tmin = 0.614, Tmax = 0.663Rint = 0.146
14103 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0751098 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 0.97Δρmax = 1.32 e Å3
5138 reflectionsΔρmin = 0.58 e Å3
368 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.00000.00001.00000.0357 (3)
Ni20.07930 (7)0.24578 (3)0.88362 (4)0.0416 (3)
N10.0186 (4)0.1420 (2)0.9063 (2)0.0332 (9)
N20.0473 (4)0.11377 (19)0.9860 (2)0.0338 (9)
N30.2129 (4)0.0283 (2)1.0484 (3)0.0434 (10)
N40.1185 (5)0.2968 (2)0.9214 (3)0.0502 (11)
N50.1604 (5)0.3551 (2)0.8698 (3)0.0525 (11)
N60.2903 (4)0.2099 (2)0.8443 (3)0.0506 (11)
O10.0447 (3)0.02165 (18)0.88104 (19)0.0391 (8)
O20.0350 (4)0.23782 (18)0.7661 (2)0.0441 (8)
O30.1899 (5)0.0024 (2)0.7669 (3)0.0712 (14)
H30.14300.01220.80370.107*
O40.1147 (3)0.23505 (17)1.0063 (2)0.0395 (8)
C10.0280 (5)0.0917 (3)0.8579 (3)0.0338 (11)
C20.0716 (5)0.1143 (3)0.7758 (3)0.0398 (11)
C30.0407 (5)0.1859 (3)0.7368 (3)0.0411 (11)
C40.0967 (5)0.2028 (3)0.6618 (3)0.0473 (13)
H40.08200.24900.63810.057*
C50.1731 (6)0.1513 (3)0.6234 (3)0.0544 (15)
H50.20570.16310.57370.065*
C60.2008 (6)0.0828 (3)0.6585 (3)0.0566 (15)
H60.25150.04900.63230.068*
C70.1524 (6)0.0643 (3)0.7334 (3)0.0472 (13)
C80.0932 (5)0.1671 (3)1.0307 (3)0.0398 (11)
C90.1235 (7)0.1487 (3)1.1180 (4)0.0637 (18)
H9A0.13240.19331.14840.096*
H9B0.05080.11991.14540.096*
H9C0.20650.12131.11530.096*
C100.2673 (8)0.0927 (4)1.0400 (5)0.0862 (19)
H100.21640.12691.00740.103*
C110.3967 (9)0.1145 (4)1.0763 (6)0.107 (3)
H110.42510.16271.07100.129*
C120.4777 (7)0.0663 (4)1.1179 (5)0.088 (2)
H120.56580.07861.13900.105*
C130.4269 (8)0.0020 (5)1.1287 (6)0.107 (3)
H130.47920.03731.15890.129*
C140.2941 (8)0.0185 (4)1.0936 (5)0.090 (2)
H140.26070.06511.10250.108*
C150.1824 (6)0.2935 (3)0.9993 (4)0.0557 (14)
H150.14140.26681.03820.067*
C160.3044 (7)0.3272 (3)1.0250 (4)0.0666 (16)
H160.34600.32191.07890.080*
C170.3628 (7)0.3692 (4)0.9674 (5)0.0728 (18)
H170.44380.39380.98290.087*
C180.3011 (7)0.3746 (3)0.8871 (5)0.0688 (17)
H180.33980.40230.84800.083*
C190.1795 (7)0.3376 (3)0.8662 (4)0.0604 (15)
H190.13790.34090.81200.073*
C200.1519 (7)0.4020 (3)0.9337 (4)0.0663 (16)
H200.10070.38910.98310.080*
C210.2174 (9)0.4691 (4)0.9283 (5)0.091 (2)
H210.20800.50090.97330.109*
C220.2966 (9)0.4892 (4)0.8563 (5)0.088 (2)
H220.34220.53380.85270.106*
C230.3065 (8)0.4426 (4)0.7915 (5)0.088 (2)
H230.35950.45430.74230.105*
C240.2355 (7)0.3765 (3)0.7999 (4)0.0719 (17)
H240.24040.34540.75430.086*
C250.3903 (6)0.2194 (3)0.8929 (4)0.0618 (15)
H250.36650.23540.94700.074*
C260.5244 (7)0.2068 (4)0.8675 (5)0.0719 (18)
H260.58880.21230.90420.086*
C270.5625 (7)0.1861 (4)0.7873 (5)0.0825 (19)
H270.65350.17890.76830.099*
C280.4647 (7)0.1759 (4)0.7351 (5)0.086 (2)
H280.48760.16170.68030.103*
C290.3281 (7)0.1878 (4)0.7675 (4)0.0682 (16)
H290.26120.17970.73300.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0354 (5)0.0393 (5)0.0350 (5)0.0006 (4)0.0142 (4)0.0001 (4)
Ni20.0364 (4)0.0471 (4)0.0422 (4)0.0048 (3)0.0081 (3)0.0048 (3)
N10.026 (2)0.0410 (19)0.033 (2)0.0001 (16)0.0076 (17)0.0064 (17)
N20.035 (2)0.0358 (19)0.032 (2)0.0048 (17)0.0112 (17)0.0031 (16)
N30.039 (2)0.047 (2)0.046 (2)0.004 (2)0.012 (2)0.0028 (19)
N40.048 (3)0.048 (2)0.055 (3)0.002 (2)0.008 (2)0.005 (2)
N50.055 (3)0.050 (2)0.053 (3)0.015 (2)0.009 (2)0.010 (2)
N60.036 (2)0.058 (2)0.058 (3)0.001 (2)0.009 (2)0.003 (2)
O10.040 (2)0.0467 (18)0.0337 (18)0.0003 (16)0.0150 (16)0.0000 (14)
O20.0369 (19)0.0571 (19)0.0390 (19)0.0092 (16)0.0071 (16)0.0088 (15)
O30.101 (4)0.057 (2)0.066 (3)0.011 (2)0.052 (3)0.003 (2)
O40.0376 (19)0.0430 (17)0.040 (2)0.0016 (15)0.0137 (16)0.0014 (15)
C10.025 (2)0.043 (2)0.035 (2)0.0048 (19)0.008 (2)0.001 (2)
C20.036 (3)0.050 (3)0.036 (3)0.007 (2)0.011 (2)0.005 (2)
C30.032 (3)0.053 (3)0.040 (3)0.006 (2)0.009 (2)0.005 (2)
C40.043 (3)0.058 (3)0.041 (3)0.000 (3)0.006 (3)0.009 (2)
C50.049 (3)0.073 (3)0.044 (3)0.007 (3)0.016 (3)0.011 (3)
C60.061 (4)0.063 (3)0.050 (3)0.003 (3)0.026 (3)0.004 (3)
C70.056 (3)0.044 (3)0.046 (3)0.010 (2)0.018 (3)0.001 (2)
C80.034 (3)0.046 (3)0.040 (3)0.004 (2)0.009 (2)0.000 (2)
C90.085 (5)0.053 (3)0.061 (4)0.013 (3)0.040 (4)0.009 (3)
C100.065 (4)0.075 (4)0.110 (4)0.018 (3)0.025 (4)0.030 (3)
C110.079 (5)0.086 (5)0.145 (6)0.032 (4)0.038 (5)0.029 (4)
C120.053 (4)0.085 (4)0.120 (6)0.017 (4)0.014 (4)0.018 (4)
C130.070 (5)0.095 (5)0.147 (7)0.007 (4)0.027 (5)0.022 (4)
C140.071 (4)0.066 (4)0.125 (5)0.008 (4)0.022 (4)0.009 (4)
C150.050 (3)0.060 (3)0.057 (3)0.003 (3)0.005 (3)0.001 (3)
C160.057 (4)0.074 (4)0.067 (4)0.003 (3)0.001 (3)0.002 (3)
C170.055 (4)0.071 (4)0.093 (5)0.005 (3)0.010 (4)0.010 (3)
C180.058 (4)0.057 (3)0.092 (5)0.007 (3)0.016 (4)0.011 (3)
C190.058 (3)0.056 (3)0.069 (4)0.001 (3)0.011 (3)0.010 (3)
C200.075 (4)0.066 (3)0.060 (3)0.013 (3)0.018 (3)0.005 (3)
C210.114 (5)0.082 (4)0.076 (5)0.032 (4)0.006 (4)0.004 (4)
C220.101 (5)0.072 (4)0.093 (5)0.036 (4)0.014 (4)0.013 (4)
C230.096 (5)0.090 (5)0.074 (4)0.032 (4)0.007 (4)0.025 (4)
C240.080 (4)0.066 (3)0.068 (4)0.006 (3)0.003 (3)0.002 (3)
C250.046 (3)0.073 (3)0.068 (4)0.006 (3)0.012 (3)0.007 (3)
C260.043 (3)0.089 (4)0.086 (5)0.003 (3)0.013 (3)0.007 (4)
C270.047 (4)0.099 (5)0.101 (5)0.001 (4)0.004 (4)0.002 (4)
C280.055 (4)0.122 (5)0.078 (5)0.013 (4)0.003 (4)0.002 (4)
C290.050 (3)0.095 (4)0.060 (3)0.007 (3)0.006 (3)0.006 (3)
Geometric parameters (Å, º) top
Ni1—O1i2.072 (3)C9—H9A0.9600
Ni1—O12.072 (3)C9—H9B0.9600
Ni1—N22.133 (4)C9—H9C0.9600
Ni1—N2i2.133 (4)C10—C111.408 (10)
Ni1—N3i2.230 (4)C10—H100.9300
Ni1—N32.230 (4)C11—C121.323 (10)
Ni2—N12.007 (4)C11—H110.9300
Ni2—O22.016 (3)C12—C131.363 (10)
Ni2—O42.074 (3)C12—H120.9300
Ni2—N52.152 (4)C13—C141.407 (10)
Ni2—N42.196 (5)C13—H130.9300
Ni2—N62.218 (5)C14—H140.9300
N1—C11.326 (6)C15—C161.379 (8)
N1—N21.453 (5)C15—H150.9300
N2—C81.326 (6)C16—C171.388 (8)
N3—C101.305 (7)C16—H160.9300
N3—C141.335 (8)C17—C181.380 (9)
N4—C151.351 (7)C17—H170.9300
N4—C191.362 (7)C18—C191.391 (9)
N5—C201.342 (7)C18—H180.9300
N5—C241.343 (8)C19—H190.9300
N6—C291.324 (7)C20—C211.383 (9)
N6—C251.351 (6)C20—H200.9300
O1—C11.336 (6)C21—C221.382 (10)
O2—C31.331 (6)C21—H210.9300
O3—C71.367 (6)C22—C231.348 (10)
O3—H30.8200C22—H220.9300
O4—C81.310 (6)C23—C241.396 (9)
C1—C21.509 (6)C23—H230.9300
C2—C71.442 (7)C24—H240.9300
C2—C31.467 (7)C25—C261.368 (9)
C3—C41.432 (7)C25—H250.9300
C4—C51.399 (7)C26—C271.369 (9)
C4—H40.9300C26—H260.9300
C5—C61.387 (8)C27—C281.375 (9)
C5—H50.9300C27—H270.9300
C6—C71.401 (7)C28—C291.414 (9)
C6—H60.9300C28—H280.9300
C8—C91.523 (7)C29—H290.9300
O1i—Ni1—O1180.000 (1)O3—C7—C2120.9 (4)
O1i—Ni1—N2102.49 (13)C6—C7—C2122.0 (5)
O1—Ni1—N277.51 (13)O4—C8—N2125.6 (4)
O1i—Ni1—N2i77.51 (13)O4—C8—C9116.6 (4)
O1—Ni1—N2i102.49 (13)N2—C8—C9117.8 (4)
N2—Ni1—N2i180.000 (1)C8—C9—H9A109.5
O1i—Ni1—N3i89.33 (14)C8—C9—H9B109.5
O1—Ni1—N3i90.67 (14)H9A—C9—H9B109.5
N2—Ni1—N3i89.97 (15)C8—C9—H9C109.5
N2i—Ni1—N3i90.03 (16)H9A—C9—H9C109.5
O1i—Ni1—N390.67 (14)H9B—C9—H9C109.5
O1—Ni1—N389.33 (14)N3—C10—C11125.4 (7)
N2—Ni1—N390.03 (16)N3—C10—H10117.3
N2i—Ni1—N389.97 (15)C11—C10—H10117.3
N3i—Ni1—N3180.0C12—C11—C10119.9 (7)
N1—Ni2—O290.71 (14)C12—C11—H11120.1
N1—Ni2—O479.35 (14)C10—C11—H11120.1
O2—Ni2—O4170.05 (13)C11—C12—C13117.4 (7)
N1—Ni2—N5173.36 (15)C11—C12—H12121.3
O2—Ni2—N595.04 (15)C13—C12—H12121.3
O4—Ni2—N594.86 (15)C12—C13—C14119.1 (8)
N1—Ni2—N496.18 (16)C12—C13—H13120.5
O2—Ni2—N490.50 (16)C14—C13—H13120.5
O4—Ni2—N490.97 (15)N3—C14—C13124.4 (7)
N5—Ni2—N487.10 (18)N3—C14—H14117.8
N1—Ni2—N691.67 (16)C13—C14—H14117.8
O2—Ni2—N690.48 (16)N4—C15—C16124.5 (6)
O4—Ni2—N689.41 (15)N4—C15—H15117.8
N5—Ni2—N684.98 (18)C16—C15—H15117.8
N4—Ni2—N6172.08 (16)C15—C16—C17117.6 (7)
C1—N1—N2113.7 (4)C15—C16—H16121.2
C1—N1—Ni2131.4 (3)C17—C16—H16121.2
N2—N1—Ni2114.3 (3)C18—C17—C16120.2 (7)
C8—N2—N1110.1 (4)C18—C17—H17119.9
C8—N2—Ni1137.8 (3)C16—C17—H17119.9
N1—N2—Ni1112.1 (2)C17—C18—C19118.4 (6)
C10—N3—C14113.6 (6)C17—C18—H18120.8
C10—N3—Ni1124.0 (4)C19—C18—H18120.8
C14—N3—Ni1122.3 (4)N4—C19—C18123.0 (6)
C15—N4—C19116.4 (5)N4—C19—H19118.5
C15—N4—Ni2123.5 (4)C18—C19—H19118.5
C19—N4—Ni2120.0 (4)N5—C20—C21121.8 (6)
C20—N5—C24116.8 (5)N5—C20—H20119.1
C20—N5—Ni2121.3 (4)C21—C20—H20119.1
C24—N5—Ni2121.5 (4)C22—C21—C20120.4 (7)
C29—N6—C25116.4 (5)C22—C21—H21119.8
C29—N6—Ni2121.1 (4)C20—C21—H21119.8
C25—N6—Ni2121.9 (4)C23—C22—C21118.6 (7)
C1—O1—Ni1114.3 (3)C23—C22—H22120.7
C3—O2—Ni2125.8 (3)C21—C22—H22120.7
C7—O3—H3109.5C22—C23—C24118.5 (7)
C8—O4—Ni2109.9 (3)C22—C23—H23120.8
N1—C1—O1122.3 (4)C24—C23—H23120.8
N1—C1—C2119.5 (4)N5—C24—C23123.9 (6)
O1—C1—C2118.1 (4)N5—C24—H24118.0
C7—C2—C3117.1 (4)C23—C24—H24118.0
C7—C2—C1118.9 (4)N6—C25—C26123.9 (6)
C3—C2—C1123.9 (4)N6—C25—H25118.1
O2—C3—C4116.3 (4)C26—C25—H25118.1
O2—C3—C2125.2 (4)C25—C26—C27119.1 (7)
C4—C3—C2118.5 (4)C25—C26—H26120.4
C5—C4—C3121.3 (5)C27—C26—H26120.4
C5—C4—H4119.3C26—C27—C28119.2 (7)
C3—C4—H4119.3C26—C27—H27120.4
C6—C5—C4120.8 (5)C28—C27—H27120.4
C6—C5—H5119.6C27—C28—C29117.8 (7)
C4—C5—H5119.6C27—C28—H28121.1
C5—C6—C7120.1 (5)C29—C28—H28121.1
C5—C6—H6119.9N6—C29—C28123.5 (6)
C7—C6—H6119.9N6—C29—H29118.2
O3—C7—C6117.1 (5)C28—C29—H29118.2
O2—Ni2—N1—C11.3 (4)N4—Ni2—O2—C380.9 (4)
O4—Ni2—N1—C1178.3 (4)N6—Ni2—O2—C3106.9 (4)
N5—Ni2—N1—C1148.8 (14)N1—Ni2—O4—C86.2 (3)
N4—Ni2—N1—C191.9 (4)O2—Ni2—O4—C83.8 (10)
N6—Ni2—N1—C189.2 (4)N5—Ni2—O4—C8170.5 (3)
O2—Ni2—N1—N2172.0 (3)N4—Ni2—O4—C8102.3 (3)
O4—Ni2—N1—N27.6 (3)N6—Ni2—O4—C885.6 (3)
N5—Ni2—N1—N221.9 (17)N2—N1—C1—O10.9 (6)
N4—Ni2—N1—N297.4 (3)Ni2—N1—C1—O1169.9 (3)
N6—Ni2—N1—N281.5 (3)N2—N1—C1—C2175.6 (4)
C1—N1—N2—C8180.0 (4)Ni2—N1—C1—C213.7 (7)
Ni2—N1—N2—C87.7 (5)Ni1—O1—C1—N12.7 (6)
C1—N1—N2—Ni11.3 (5)Ni1—O1—C1—C2173.8 (3)
Ni2—N1—N2—Ni1173.68 (17)N1—C1—C2—C7164.7 (5)
O1i—Ni1—N2—C80.1 (5)O1—C1—C2—C711.9 (7)
O1—Ni1—N2—C8179.9 (5)N1—C1—C2—C313.2 (7)
N2i—Ni1—N2—C818 (100)O1—C1—C2—C3170.2 (4)
N3i—Ni1—N2—C889.2 (5)Ni2—O2—C3—C4159.8 (4)
N3—Ni1—N2—C890.8 (5)Ni2—O2—C3—C219.3 (7)
O1i—Ni1—N2—N1178.0 (3)C7—C2—C3—O2178.3 (5)
O1—Ni1—N2—N12.0 (3)C1—C2—C3—O23.8 (8)
N2i—Ni1—N2—N1160 (100)C7—C2—C3—C42.6 (7)
N3i—Ni1—N2—N192.7 (3)C1—C2—C3—C4175.3 (5)
N3—Ni1—N2—N187.3 (3)O2—C3—C4—C5177.3 (5)
O1i—Ni1—N3—C10118.7 (5)C2—C3—C4—C53.5 (8)
O1—Ni1—N3—C1061.3 (5)C3—C4—C5—C62.2 (9)
N2—Ni1—N3—C1016.2 (5)C4—C5—C6—C70.1 (9)
N2i—Ni1—N3—C10163.8 (5)C5—C6—C7—O3176.4 (6)
N3i—Ni1—N3—C10148 (100)C5—C6—C7—C20.9 (9)
O1i—Ni1—N3—C1457.0 (5)C3—C2—C7—O3177.7 (5)
O1—Ni1—N3—C14123.0 (5)C1—C2—C7—O30.4 (8)
N2—Ni1—N3—C14159.5 (5)C3—C2—C7—C60.5 (8)
N2i—Ni1—N3—C1420.5 (5)C1—C2—C7—C6177.6 (5)
N3i—Ni1—N3—C1436 (100)Ni2—O4—C8—N24.1 (6)
N1—Ni2—N4—C1563.4 (4)Ni2—O4—C8—C9176.2 (4)
O2—Ni2—N4—C15154.1 (4)N1—N2—C8—O42.2 (7)
O4—Ni2—N4—C1516.0 (4)Ni1—N2—C8—O4179.7 (4)
N5—Ni2—N4—C15110.8 (4)N1—N2—C8—C9177.5 (4)
N6—Ni2—N4—C15108.7 (12)Ni1—N2—C8—C90.6 (8)
N1—Ni2—N4—C19120.4 (4)C14—N3—C10—C112.3 (11)
O2—Ni2—N4—C1929.6 (4)Ni1—N3—C10—C11173.7 (7)
O4—Ni2—N4—C19160.2 (4)N3—C10—C11—C125.3 (15)
N5—Ni2—N4—C1965.4 (4)C10—C11—C12—C134.6 (14)
N6—Ni2—N4—C1967.5 (14)C11—C12—C13—C141.7 (14)
N1—Ni2—N5—C2060.4 (17)C10—N3—C14—C130.8 (11)
O2—Ni2—N5—C20149.7 (5)Ni1—N3—C14—C13176.9 (7)
O4—Ni2—N5—C2031.3 (5)C12—C13—C14—N31.1 (14)
N4—Ni2—N5—C2059.4 (5)C19—N4—C15—C161.4 (8)
N6—Ni2—N5—C20120.3 (5)Ni2—N4—C15—C16177.7 (4)
N1—Ni2—N5—C24111.6 (15)N4—C15—C16—C172.3 (9)
O2—Ni2—N5—C2438.3 (5)C15—C16—C17—C181.8 (9)
O4—Ni2—N5—C24140.7 (5)C16—C17—C18—C190.6 (10)
N4—Ni2—N5—C24128.6 (5)C15—N4—C19—C180.0 (8)
N6—Ni2—N5—C2451.7 (5)Ni2—N4—C19—C18176.5 (4)
N1—Ni2—N6—C2984.5 (5)C17—C18—C19—N40.4 (9)
O2—Ni2—N6—C296.3 (5)C24—N5—C20—C210.2 (10)
O4—Ni2—N6—C29163.8 (5)Ni2—N5—C20—C21172.2 (5)
N5—Ni2—N6—C29101.3 (5)N5—C20—C21—C221.4 (12)
N4—Ni2—N6—C29103.4 (12)C20—C21—C22—C231.2 (13)
N1—Ni2—N6—C25105.2 (4)C21—C22—C23—C240.4 (13)
O2—Ni2—N6—C25164.1 (4)C20—N5—C24—C231.9 (10)
O4—Ni2—N6—C2525.8 (4)Ni2—N5—C24—C23170.5 (5)
N5—Ni2—N6—C2569.1 (4)C22—C23—C24—N52.0 (12)
N4—Ni2—N6—C2567.0 (14)C29—N6—C25—C260.6 (9)
O1i—Ni1—O1—C1157 (100)Ni2—N6—C25—C26171.4 (5)
N2—Ni1—O1—C12.4 (3)N6—C25—C26—C272.6 (11)
N2i—Ni1—O1—C1177.6 (3)C25—C26—C27—C282.3 (11)
N3i—Ni1—O1—C192.3 (3)C26—C27—C28—C290.2 (12)
N3—Ni1—O1—C187.7 (3)C25—N6—C29—C281.6 (10)
N1—Ni2—O2—C315.3 (4)Ni2—N6—C29—C28169.3 (6)
O4—Ni2—O2—C317.6 (10)C27—C28—C29—N61.8 (12)
N5—Ni2—O2—C3168.1 (4)
Symmetry code: (i) x, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···Cgii0.932.523.428 (4)166
Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Ni3(C9H7N2O4)2(C5H5N)8]
Mr1223.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.9349 (18), 18.230 (3), 16.262 (2)
β (°) 96.663 (2)
V3)2925.3 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.02
Crystal size (mm)0.53 × 0.45 × 0.44
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.614, 0.663
No. of measured, independent and
observed [I > 2σ(I)] reflections
14103, 5138, 3047
Rint0.146
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.210, 0.97
No. of reflections5138
No. of parameters368
No. of restraints1098
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.32, 0.58

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···Cgi0.932.523.428 (4)165.97
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

We acknowledge financial support from the National Natural Science Foundation of China (grant No. 20671048).

References

First citationJohn, R. P., Lee, K. J. & Lah, M. S. (2004). Chem. Commun. pp. 2660–2661.  Web of Science CSD CrossRef Google Scholar
First citationLin, S., Liu, S. X. & Lin, B. Z. (2002). Inorg. Chim. Acta, 328, 69–73.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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