PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m746.
Published online 2009 June 6. doi:  10.1107/S1600536809020534
PMCID: PMC2969366

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

Abstract

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 [triangle]); Lin et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m746-scheme1.jpg

Experimental

Crystal data

  • [Ni3(C9H7N2O4)2(C5H5N)8]
  • M r = 1223.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m746-efi1.jpg
  • 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 [triangle]) T min = 0.614, T max = 0.663
  • 14103 measured reflections
  • 5138 independent reflections
  • 3047 reflections with I > 2σ(I)
  • R int = 0.146

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020534/cv2565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020534/cv2565Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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)].

Figures

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.
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.

Crystal data

[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

Bruker SMART CCD area-detector diffractometer5138 independent reflections
Radiation source: fine-focus sealed tube3047 reflections with I > 2σ(I)
graphiteRint = 0.146
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.614, Tmax = 0.663k = −16→21
14103 measured reflectionsl = −19→19

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)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 0.97w = 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

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
Ni10.00000.00001.00000.0357 (3)
Ni2−0.07930 (7)0.24578 (3)0.88362 (4)0.0416 (3)
N1−0.0186 (4)0.1420 (2)0.9063 (2)0.0332 (9)
N2−0.0473 (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)
N5−0.1604 (5)0.3551 (2)0.8698 (3)0.0525 (11)
N6−0.2903 (4)0.2099 (2)0.8443 (3)0.0506 (11)
O10.0447 (3)0.02165 (18)0.88104 (19)0.0391 (8)
O2−0.0350 (4)0.23782 (18)0.7661 (2)0.0441 (8)
O30.1899 (5)−0.0024 (2)0.7669 (3)0.0712 (14)
H30.1430−0.01220.80370.107*
O4−0.1147 (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)
C8−0.0932 (5)0.1671 (3)1.0307 (3)0.0398 (11)
C9−0.1235 (7)0.1487 (3)1.1180 (4)0.0637 (18)
H9A−0.13240.19331.14840.096*
H9B−0.05080.11991.14540.096*
H9C−0.20650.12131.11530.096*
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)
H130.4792−0.03731.15890.129*
C140.2941 (8)−0.0185 (4)1.0936 (5)0.090 (2)
H140.2607−0.06511.10250.108*
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*
C20−0.1519 (7)0.4020 (3)0.9337 (4)0.0663 (16)
H20−0.10070.38910.98310.080*
C21−0.2174 (9)0.4691 (4)0.9283 (5)0.091 (2)
H21−0.20800.50090.97330.109*
C22−0.2966 (9)0.4892 (4)0.8563 (5)0.088 (2)
H22−0.34220.53380.85270.106*
C23−0.3065 (8)0.4426 (4)0.7915 (5)0.088 (2)
H23−0.35950.45430.74230.105*
C24−0.2355 (7)0.3765 (3)0.7999 (4)0.0719 (17)
H24−0.24040.34540.75430.086*
C25−0.3903 (6)0.2194 (3)0.8929 (4)0.0618 (15)
H25−0.36650.23540.94700.074*
C26−0.5244 (7)0.2068 (4)0.8675 (5)0.0719 (18)
H26−0.58880.21230.90420.086*
C27−0.5625 (7)0.1861 (4)0.7873 (5)0.0825 (19)
H27−0.65350.17890.76830.099*
C28−0.4647 (7)0.1759 (4)0.7351 (5)0.086 (2)
H28−0.48760.16170.68030.103*
C29−0.3281 (7)0.1878 (4)0.7675 (4)0.0682 (16)
H29−0.26120.17970.73300.082*

Atomic displacement parameters (Å2)

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, °)

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—C1−1.3 (4)N4—Ni2—O2—C380.9 (4)
O4—Ni2—N1—C1178.3 (4)N6—Ni2—O2—C3−106.9 (4)
N5—Ni2—N1—C1148.8 (14)N1—Ni2—O4—C8−6.2 (3)
N4—Ni2—N1—C1−91.9 (4)O2—Ni2—O4—C8−3.8 (10)
N6—Ni2—N1—C189.2 (4)N5—Ni2—O4—C8170.5 (3)
O2—Ni2—N1—N2−172.0 (3)N4—Ni2—O4—C8−102.3 (3)
O4—Ni2—N1—N27.6 (3)N6—Ni2—O4—C885.6 (3)
N5—Ni2—N1—N2−21.9 (17)N2—N1—C1—O10.9 (6)
N4—Ni2—N1—N297.4 (3)Ni2—N1—C1—O1−169.9 (3)
N6—Ni2—N1—N2−81.5 (3)N2—N1—C1—C2−175.6 (4)
C1—N1—N2—C8180.0 (4)Ni2—N1—C1—C213.7 (7)
Ni2—N1—N2—C8−7.7 (5)Ni1—O1—C1—N1−2.7 (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—C8−0.1 (5)O1—C1—C2—C7−11.9 (7)
O1—Ni1—N2—C8179.9 (5)N1—C1—C2—C3−13.2 (7)
N2i—Ni1—N2—C8−18 (100)O1—C1—C2—C3170.2 (4)
N3i—Ni1—N2—C889.2 (5)Ni2—O2—C3—C4−159.8 (4)
N3—Ni1—N2—C8−90.8 (5)Ni2—O2—C3—C219.3 (7)
O1i—Ni1—N2—N1178.0 (3)C7—C2—C3—O2178.3 (5)
O1—Ni1—N2—N1−2.0 (3)C1—C2—C3—O2−3.8 (8)
N2i—Ni1—N2—N1160 (100)C7—C2—C3—C4−2.6 (7)
N3i—Ni1—N2—N1−92.7 (3)C1—C2—C3—C4175.3 (5)
N3—Ni1—N2—N187.3 (3)O2—C3—C4—C5−177.3 (5)
O1i—Ni1—N3—C10−118.7 (5)C2—C3—C4—C53.5 (8)
O1—Ni1—N3—C1061.3 (5)C3—C4—C5—C6−2.2 (9)
N2—Ni1—N3—C10−16.2 (5)C4—C5—C6—C7−0.1 (9)
N2i—Ni1—N3—C10163.8 (5)C5—C6—C7—O3−176.4 (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—C14−123.0 (5)C1—C2—C7—O3−0.4 (8)
N2—Ni1—N3—C14159.5 (5)C3—C2—C7—C60.5 (8)
N2i—Ni1—N3—C14−20.5 (5)C1—C2—C7—C6−177.6 (5)
N3i—Ni1—N3—C14−36 (100)Ni2—O4—C8—N24.1 (6)
N1—Ni2—N4—C15−63.4 (4)Ni2—O4—C8—C9−176.2 (4)
O2—Ni2—N4—C15−154.1 (4)N1—N2—C8—O42.2 (7)
O4—Ni2—N4—C1516.0 (4)Ni1—N2—C8—O4−179.7 (4)
N5—Ni2—N4—C15110.8 (4)N1—N2—C8—C9−177.5 (4)
N6—Ni2—N4—C15108.7 (12)Ni1—N2—C8—C90.6 (8)
N1—Ni2—N4—C19120.4 (4)C14—N3—C10—C11−2.3 (11)
O2—Ni2—N4—C1929.6 (4)Ni1—N3—C10—C11173.7 (7)
O4—Ni2—N4—C19−160.2 (4)N3—C10—C11—C125.3 (15)
N5—Ni2—N4—C19−65.4 (4)C10—C11—C12—C13−4.6 (14)
N6—Ni2—N4—C19−67.5 (14)C11—C12—C13—C141.7 (14)
N1—Ni2—N5—C2060.4 (17)C10—N3—C14—C13−0.8 (11)
O2—Ni2—N5—C20−149.7 (5)Ni1—N3—C14—C13−176.9 (7)
O4—Ni2—N5—C2031.3 (5)C12—C13—C14—N31.1 (14)
N4—Ni2—N5—C20−59.4 (5)C19—N4—C15—C16−1.4 (8)
N6—Ni2—N5—C20120.3 (5)Ni2—N4—C15—C16−177.7 (4)
N1—Ni2—N5—C24−111.6 (15)N4—C15—C16—C172.3 (9)
O2—Ni2—N5—C2438.3 (5)C15—C16—C17—C18−1.8 (9)
O4—Ni2—N5—C24−140.7 (5)C16—C17—C18—C190.6 (10)
N4—Ni2—N5—C24128.6 (5)C15—N4—C19—C180.0 (8)
N6—Ni2—N5—C24−51.7 (5)Ni2—N4—C19—C18176.5 (4)
N1—Ni2—N6—C29−84.5 (5)C17—C18—C19—N40.4 (9)
O2—Ni2—N6—C296.3 (5)C24—N5—C20—C210.2 (10)
O4—Ni2—N6—C29−163.8 (5)Ni2—N5—C20—C21−172.2 (5)
N5—Ni2—N6—C29101.3 (5)N5—C20—C21—C221.4 (12)
N4—Ni2—N6—C29103.4 (12)C20—C21—C22—C23−1.2 (13)
N1—Ni2—N6—C25105.2 (4)C21—C22—C23—C24−0.4 (13)
O2—Ni2—N6—C25−164.1 (4)C20—N5—C24—C23−1.9 (10)
O4—Ni2—N6—C2525.8 (4)Ni2—N5—C24—C23170.5 (5)
N5—Ni2—N6—C25−69.1 (4)C22—C23—C24—N52.0 (12)
N4—Ni2—N6—C25−67.0 (14)C29—N6—C25—C260.6 (9)
O1i—Ni1—O1—C1−157 (100)Ni2—N6—C25—C26171.4 (5)
N2—Ni1—O1—C12.4 (3)N6—C25—C26—C27−2.6 (11)
N2i—Ni1—O1—C1−177.6 (3)C25—C26—C27—C282.3 (11)
N3i—Ni1—O1—C192.3 (3)C26—C27—C28—C29−0.2 (12)
N3—Ni1—O1—C1−87.7 (3)C25—N6—C29—C281.6 (10)
N1—Ni2—O2—C3−15.3 (4)Ni2—N6—C29—C28−169.3 (6)
O4—Ni2—O2—C3−17.6 (10)C27—C28—C29—N6−1.8 (12)
N5—Ni2—O2—C3168.1 (4)

Symmetry codes: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C27—H27···Cgii0.932.523.428 (4)166

Symmetry codes: (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2565).

References

  • John, R. P., Lee, K. J. & Lah, M. S. (2004). Chem. Commun. pp. 2660–2661. [PubMed]
  • Lin, S., Liu, S. X. & Lin, B. Z. (2002). Inorg. Chim. Acta, 328, 69–73.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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