supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2330-m2331    [ doi:10.1107/S1600536807039001 ]

A binuclear unsymmetrical compartmental NiII complex: [[mu]-11,24-dimethyl-16,19-dioxa-3,7,15,20-tetraazatricyclo[20.3.1.19,13]heptacosa-1(25),2,7,9,11,13(27),14,20,22(26),23-decaene-26,27-diolato]bis[diaquanickel(II)] bis(perchlorate) tetrahydrate

S. Anbu, M. Kandaswamy and B. Varghese

Abstract top

In the title compound, [Ni2(C23H24N4O4)(H2O)4](ClO4)2·4H2O, each NiII atom is coordinated by two bridging phenoxide O atoms, two azomethine N atoms and two water molecules in a slightly distorted octahedral geometry. The crystal packing is stabilized by intermolecular O-H...O hydrogen bonds mediated through the water molecules and perchlorate anions. The bis(aminooxy)ethane and diaminopropane groups are disordered across the centre of the molecule, and as a result the complex molecule and the crystal structure is centrosymmetric.

Comment top

Dinuclear metal complexes of diphenolic Schiff base macrocyclic ligands have attracted much attention as they have contributed significantly to the understanding of the relationship between chemical behaviour and structural properties (Hong et al., 2005). Complexes of ligands which contain two or more metal ions in close proximity are important as potential catalysts (Mckenzie & Robson, 1988), models of reaction centers for metalloenzymes (Tsou et al., 1982) and non-linear optical materials (Lacroix et al., 2001). Stability of the complexes depend upon the cavity size of the ligand and the radius of the metal ion. In continuation of our earlier studies (Krishnapriya & Kandaswamy, 2005) we report here the crystal structure of a dinuclear NiII complex with a ligand containing two compartments with different compartmental sizes, in which one of the compartments has 1,3-diamino propane and the another compartment has 1,2-bis(aminooxy)ethane.

The coordination geometry at each NiII ion is distorted octahedral (Fig. 1), in which the equatorial plane is formed by two bridging phenoxide O atoms and two azomethine N atoms while the axial coordination sites are occupied by two water molecules. The trans angles at the NiII centres are close to 180°, ranging from 170.78 (5) to 173.88 (4)°. All other angles subtended at the NiII centres are close to 90°, ranging from 81.64 (4) to 99.47 (5), which indicates a slightly distorted octahedral geometry of NiII atoms. The Ni—N and Ni—O bond lengths lie in the range 1.9984 (13)–2.0263 (13) Å and 2.0122 (10)–2.1604 (11) Å, respectively, and the bond lengths are comparable to those observed in a related structure (Black et al., 1998). The two benzene rings in the molecule are parallel to each other, within the limits of standard deviations.

The crystal packing is stabilized by intermolecular O—H···O hydrogen bonding involving the water molecules and perchlorate anions. The inversion disorder of bis-aminooxy ethane and diamino propane groups shows an apparent centrosymmetry in the crystal structure.

Related literature top

For synthesis, see: Dixon & Weiss (1984); Verani et al. (2000). For general background on dinuclear metal complexes, see: Hong et al. (2005); Krishnapriya & Kandaswamy (2005); Lacroix (2001); Mckenzie & Robson (1988); Tsou et al. (1982). For a related structure, see: Black et al. (1998).

Experimental top

To a vigorously stirred suspension of N,N'-propylene-bis(3-formyl-5-methyl-salicylaldimino)nickel(II) (Verani et al., 2000) (1.0 g, 2.36 mmol) in methanol (25 ml), a methanolic solution (10 ml) of Ni(ClO4)2·6H2O (0.86 g, 2.36 mmol) was added slowly and the mixture was stirred for 15 min to obtain a clear solution. Then a methanolic solution (5 ml) of 1,2-bis(aminooxy)ethane (Dixon & Weiss, 1984) (0.10 g, 2.36 mmol) was added dropwise to the above solution. The resulting solution was refluxed for 3 h. A pale green coloured solid was separated on evaporating the solution at 398 K and the compound was washed with ether and dried. Green crystals suitable for X-ray analysis were obtained after several days by slow evaporation of a acetonitrile solution (yield 69%).

Refinement top

Eventhough there is only one molecule in the unit cell and molecule does not possess center of symmetry, a near perfect inversion disorder makes it possible for structure to be solved in the centrosymmetric space group P1. Physically, it may be interpreted as, 50% of the unit cells are inversion of the other 50%. Hence, strictly speaking, the space group of the unit cell is P1. The structure could be solved and refined to the same R-factor in P1 space group with appropriate disorder on either side of the molecule. However, The shift/e.s.d. parameters were oscillating rather than converging. Therefore, it was decided to adopt the P1 space group for solving and refining the structure, with the bis-aminooxy ethane and diamino propane groups disordered across the inversion center. As electron densities of these groups may overlap at many places, the unrestrained refinement will lead to abnormal geometries. Therefore the following restraints on distances were applied to atoms of the disordered groups: N—O = 1.450 (1) Å, N—C = 1.470 (1) Å, C—C = 1.530 (1) Å and O—C = 1.470 (1) Å. Water H atoms were located in a difference map and refined isotropically, with O—H and H···H distance restraints of 0.85 (1) and 1.38 (1) Å, respectively. Further Ni···H distances were fixed at 2.6Å for H atoms of coordinated water molecules. All the hydrogen atoms except the ones at disordered sites were located in difference maps. They were relocated in idealized positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2–1.5 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The unit-cell contents of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Only one disorder component is shown. Symmetry code (i): −x, −y, −z
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. C-bound H atoms have been omitted for clarity. Both disorder components are shown.
[µ-11,24-dimethyl-16,19-dioxa-3,7,15,20- tetraazatricyclo[20.3.1.19,13]heptacosa- 1(25),2,7,9,11,13 (27),14,20,22 (26),23-decaene-26,27- diolato]bis[diaquanickel(II)] bis(perchlorate) tetrahydrate top
Crystal data top
[Ni2(C23H24N4O4)(H2O)4](ClO4)2·4H2OZ = 1
Mr = 880.91F000 = 456
Triclinic, P1Dx = 1.674 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.5227 (3) ÅCell parameters from 7997 reflections
b = 10.3081 (3) Åθ = 2.2–33.5º
c = 12.2764 (5) ŵ = 1.32 mm−1
α = 107.167 (2)ºT = 293 (2) K
β = 94.932 (2)ºBlock, green
γ = 103.092 (2)º0.30 × 0.20 × 0.20 mm
V = 873.89 (6) Å3
Data collection top
Bruker Kappa-APEXII area-detector
diffractometer		7176 independent reflections
Radiation source: fine-focus sealed tube5831 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 293(2) Kθmax = 37.3º
ω and φ scansθmin = 1.8º
Absorption correction: multi-scan
(Blessing, 1995)		h = −9→12
Tmin = 0.732, Tmax = 0.825k = −15→15
24651 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.113  w = 1/[σ2(Fo2) + (0.067P)2 + 0.1283P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
7176 reflectionsΔρmax = 0.59 e Å−3
295 parametersΔρmin = −0.36 e Å−3
25 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni2(C23H24N4O4)(H2O)4](ClO4)2·4H2Oγ = 103.092 (2)º
Mr = 880.91V = 873.89 (6) Å3
Triclinic, P1Z = 1
a = 7.5227 (3) ÅMo Kα
b = 10.3081 (3) ŵ = 1.32 mm−1
c = 12.2764 (5) ÅT = 293 (2) K
α = 107.167 (2)º0.30 × 0.20 × 0.20 mm
β = 94.932 (2)º
Data collection top
Bruker Kappa-APEXII area-detector
diffractometer		7176 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		5831 reflections with I > 2σ(I)
Tmin = 0.732, Tmax = 0.825Rint = 0.020
24651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03425 restraints
wR(F2) = 0.113H atoms treated by a mixture of
independent and constrained refinement
S = 1.04Δρmax = 0.59 e Å−3
7176 reflectionsΔρmin = −0.36 e Å−3
295 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*/UeqOcc. (<1)
C10.0971 (2)0.15878 (19)−0.23328 (13)0.0444 (3)
H10.12150.1875−0.29680.053*
C20.13711 (19)0.27002 (16)−0.12198 (13)0.0371 (3)
C30.2263 (2)0.40586 (18)−0.12170 (15)0.0428 (3)
H30.25840.4173−0.19040.051*
C40.26796 (19)0.52242 (17)−0.02416 (16)0.0433 (3)
C50.2108 (2)0.50310 (16)0.07479 (15)0.0414 (3)
H50.23140.58140.14060.050*
C60.12309 (18)0.37082 (15)0.08068 (12)0.0353 (3)
C70.08787 (16)0.24933 (14)−0.01828 (12)0.0322 (2)
C80.0622 (2)0.37031 (16)0.18958 (13)0.0412 (3)
H80.06270.45700.24140.049*
C90.3681 (3)0.66680 (19)−0.0250 (2)0.0554 (4)
H9C0.39630.6606−0.10090.083*
H9B0.48090.70170.02970.083*
H9A0.29080.7297−0.00440.083*
N1−0.00792 (18)−0.26233 (14)−0.22116 (10)0.0388 (2)
N20.03246 (19)0.02623 (15)−0.25431 (10)0.0415 (3)
O50.0838 (8)−0.2869 (9)−0.3212 (5)0.0556 (13)0.50
O60.0362 (10)−0.0402 (6)−0.3736 (5)0.0577 (14)0.50
C13−0.0346 (6)−0.2933 (5)−0.4219 (3)0.0556 (9)0.50
H13A−0.1384−0.3761−0.44120.067*0.50
H13B0.0337−0.3050−0.48610.067*0.50
C14−0.1078 (7)−0.1681 (5)−0.4099 (4)0.0531 (10)0.50
H14B−0.1774−0.1781−0.48350.064*0.50
H14A−0.1918−0.1638−0.35400.064*0.50
C10−0.0080 (15)−0.0655 (8)−0.3768 (6)0.0563 (18)0.50
H10B0.1043−0.0476−0.40950.068*0.50
H10A−0.0988−0.0351−0.41730.068*0.50
C11−0.0782 (7)−0.2234 (5)−0.4048 (4)0.0521 (10)0.50
H11C−0.0815−0.2676−0.48680.063*0.50
H11D−0.2044−0.2444−0.39010.063*0.50
C120.0324 (12)−0.2907 (11)−0.3390 (6)0.0520 (16)0.50
H12B0.0008−0.3916−0.37790.062*0.50
H12A0.1635−0.2531−0.33690.062*0.50
O10.29581 (15)−0.01748 (13)−0.08643 (10)0.0431 (2)
O20.00840 (13)0.12288 (10)−0.01495 (8)0.03364 (18)
O3−0.29405 (15)−0.11087 (13)−0.15299 (10)0.0420 (2)
O4−0.5126 (3)−0.3673 (2)−0.30007 (17)0.0826 (5)
O70.6566 (5)0.3989 (3)−0.4449 (3)0.1479 (12)
O80.5456 (5)0.1699 (4)−0.5264 (3)0.1534 (14)
O90.4749 (5)0.2772 (5)−0.3522 (3)0.1690 (15)
O100.7589 (4)0.2542 (3)−0.3600 (2)0.1299 (10)
O11−0.4866 (3)0.03465 (19)−0.25509 (14)0.0650 (4)
Cl10.60736 (8)0.27329 (6)−0.42118 (4)0.06240 (13)
Ni10.00424 (2)−0.064272 (18)−0.128772 (13)0.03218 (6)
H1A0.3359 (15)0.028 (2)−0.0145 (8)0.073 (8)*
H1B0.3590 (14)0.023 (2)−0.1257 (13)0.054 (6)*
H3B−0.3473 (15)−0.1940 (11)−0.191 (2)0.077 (8)*
H3A−0.3323 (15)−0.0541 (17)−0.180 (2)0.076 (8)*
H11A−0.518 (5)−0.030 (2)−0.3197 (15)0.110 (13)*
H11B−0.443 (4)0.1130 (16)−0.266 (2)0.099 (11)*
H4A−0.498 (6)−0.449 (2)−0.318 (3)0.150 (18)*
H4B−0.589 (4)−0.357 (3)−0.348 (2)0.101 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0518 (8)0.0572 (9)0.0346 (7)0.0199 (7)0.0128 (6)0.0246 (7)
C20.0355 (6)0.0454 (7)0.0374 (7)0.0126 (5)0.0087 (5)0.0214 (6)
C30.0399 (6)0.0514 (8)0.0477 (8)0.0141 (6)0.0125 (6)0.0289 (7)
C40.0343 (6)0.0448 (7)0.0575 (9)0.0094 (5)0.0066 (6)0.0273 (7)
C50.0395 (6)0.0382 (7)0.0465 (8)0.0091 (5)0.0033 (6)0.0156 (6)
C60.0337 (5)0.0369 (6)0.0374 (7)0.0100 (5)0.0048 (5)0.0148 (5)
C70.0280 (5)0.0388 (6)0.0345 (6)0.0112 (4)0.0062 (4)0.0166 (5)
C80.0490 (7)0.0376 (7)0.0364 (7)0.0133 (6)0.0086 (6)0.0092 (5)
C90.0479 (8)0.0468 (9)0.0750 (13)0.0043 (7)0.0080 (8)0.0318 (9)
N10.0432 (6)0.0421 (6)0.0316 (5)0.0131 (5)0.0116 (4)0.0099 (5)
N20.0469 (6)0.0548 (7)0.0274 (5)0.0161 (5)0.0096 (4)0.0175 (5)
O50.066 (3)0.066 (2)0.040 (2)0.022 (2)0.0271 (19)0.0164 (18)
O60.081 (4)0.055 (2)0.0329 (16)0.005 (2)0.0250 (17)0.0149 (14)
C130.069 (2)0.054 (2)0.0342 (18)0.0033 (18)0.0128 (15)0.0085 (16)
C140.054 (2)0.069 (3)0.0304 (16)0.009 (2)0.0015 (13)0.014 (2)
C100.074 (5)0.067 (4)0.030 (2)0.009 (3)0.013 (2)0.027 (2)
C110.070 (3)0.054 (3)0.0280 (16)0.014 (2)0.0050 (15)0.0098 (19)
C120.073 (5)0.047 (2)0.037 (3)0.017 (3)0.027 (3)0.0095 (19)
O10.0356 (4)0.0546 (6)0.0416 (6)0.0117 (4)0.0110 (4)0.0180 (5)
O20.0370 (4)0.0354 (4)0.0302 (4)0.0085 (3)0.0089 (3)0.0130 (4)
O30.0366 (5)0.0490 (6)0.0403 (6)0.0107 (4)0.0044 (4)0.0152 (5)
O40.0912 (13)0.0749 (12)0.0683 (11)0.0135 (10)−0.0104 (9)0.0165 (9)
O70.179 (3)0.0998 (18)0.171 (3)0.0049 (18)−0.002 (2)0.084 (2)
O80.171 (3)0.138 (2)0.0934 (18)0.050 (2)−0.0225 (18)−0.0410 (17)
O90.139 (3)0.268 (5)0.126 (2)0.066 (3)0.080 (2)0.076 (3)
O100.138 (2)0.145 (2)0.1073 (18)0.0674 (19)−0.0220 (16)0.0308 (17)
O110.0833 (10)0.0713 (10)0.0509 (8)0.0242 (8)0.0179 (7)0.0304 (8)
Cl10.0776 (3)0.0597 (3)0.0468 (2)0.0139 (2)0.0083 (2)0.0164 (2)
Ni10.03454 (9)0.03765 (10)0.02645 (9)0.00998 (6)0.00817 (6)0.01227 (7)
Geometric parameters (Å, °) top
C1—N21.280 (2)C13—H13A0.97
C1—C21.456 (2)C13—H13B0.97
C1—H10.93C14—H14B0.97
C2—C31.408 (2)C14—H14A0.97
C2—C71.4174 (18)C10—C111.515 (7)
C3—C41.375 (3)C10—H10B0.97
C3—H30.93C10—H10A0.97
C4—C51.376 (2)C11—C121.518 (8)
C4—C91.512 (2)C11—H11C0.97
C5—C61.400 (2)C11—H11D0.97
C5—H50.93C12—H12B0.97
C6—C71.418 (2)C12—H12A0.97
C6—C81.451 (2)O1—Ni12.1191 (11)
C7—O21.3193 (16)O1—H1A0.858 (9)
C8—N1i1.277 (2)O1—H1B0.838 (8)
C8—H80.93O2—Ni12.0122 (10)
C9—H9C0.96O2—Ni1i2.0297 (10)
C9—H9B0.96O3—Ni12.1604 (11)
C9—H9A0.96O3—H3B0.831 (9)
N1—C8i1.277 (2)O3—H3A0.846 (9)
N1—O51.445 (5)O4—H4A0.839 (10)
N1—C121.461 (7)O4—H4B0.831 (10)
N1—Ni11.9984 (13)O7—Cl11.386 (2)
N2—O61.427 (5)O8—Cl11.371 (2)
N2—C101.483 (7)O9—Cl11.362 (3)
N2—Ni12.0263 (13)O10—Cl11.394 (3)
O5—C131.437 (6)O11—H11A0.846 (10)
O6—C141.426 (6)O11—H11B0.856 (10)
C13—C141.488 (6)Ni1—O2i2.0297 (10)
N2—C1—C2127.86 (13)O6—C14—H14A109.2
N2—C1—H1116.1C13—C14—H14A109.2
C2—C1—H1116.1H14B—C14—H14A107.9
C3—C2—C7119.81 (14)N2—C10—C11119.2 (5)
C3—C2—C1115.97 (13)N2—C10—H10B107.5
C7—C2—C1124.19 (13)C11—C10—H10B107.5
C4—C3—C2122.83 (14)N2—C10—H10A107.5
C4—C3—H3118.6C11—C10—H10A107.5
C2—C3—H3118.6H10B—C10—H10A107.0
C3—C4—C5117.12 (14)C10—C11—C12116.2 (7)
C3—C4—C9121.99 (16)C10—C11—H11C108.2
C5—C4—C9120.87 (16)C12—C11—H11C108.2
C4—C5—C6122.87 (15)C10—C11—H11D108.2
C4—C5—H5118.6C12—C11—H11D108.2
C6—C5—H5118.6H11C—C11—H11D107.4
C5—C6—C7120.13 (13)N1—C12—C11109.9 (5)
C5—C6—C8115.70 (14)N1—C12—H12B109.7
C7—C6—C8124.03 (13)C11—C12—H12B109.7
O2—C7—C2121.32 (12)N1—C12—H12A109.7
O2—C7—C6121.57 (12)C11—C12—H12A109.7
C2—C7—C6117.08 (12)H12B—C12—H12A108.2
N1i—C8—C6126.29 (14)Ni1—O1—H1A112.7 (9)
N1i—C8—H8116.9Ni1—O1—H1B117.1 (9)
C6—C8—H8116.9H1A—O1—H1B108.8 (12)
C4—C9—H9C109.5C7—O2—Ni1127.60 (8)
C4—C9—H9B109.5C7—O2—Ni1i126.25 (9)
H9C—C9—H9B109.5Ni1—O2—Ni1i98.36 (4)
C4—C9—H9A109.5Ni1—O3—H3B113.9 (9)
H9C—C9—H9A109.5Ni1—O3—H3A111.3 (9)
H9B—C9—H9A109.5H3B—O3—H3A111.6 (13)
C8i—N1—O5114.5 (3)H4A—O4—H4B113.0 (17)
C8i—N1—C12115.8 (4)H11A—O11—H11B108.9 (16)
O5—N1—C1216.4 (5)O9—Cl1—O8112.2 (3)
C8i—N1—Ni1125.50 (10)O9—Cl1—O7110.1 (3)
O5—N1—Ni1118.8 (3)O8—Cl1—O7105.8 (2)
C12—N1—Ni1118.5 (4)O9—Cl1—O10106.5 (2)
C1—N2—O6106.9 (3)O8—Cl1—O10112.06 (19)
C1—N2—C10117.7 (3)O7—Cl1—O10110.2 (2)
O6—N2—C1014.2 (5)N1—Ni1—O2170.85 (4)
C1—N2—Ni1123.23 (11)N1—Ni1—N299.47 (5)
O6—N2—Ni1127.8 (3)O2—Ni1—N289.65 (5)
C10—N2—Ni1118.9 (3)N1—Ni1—O2i89.29 (5)
C13—O5—N1111.0 (4)O2—Ni1—O2i81.64 (4)
C14—O6—N2106.3 (4)N2—Ni1—O2i170.78 (5)
O5—C13—C14114.9 (4)N1—Ni1—O190.78 (5)
O5—C13—H13A108.5O2—Ni1—O189.95 (4)
C14—C13—H13A108.5N2—Ni1—O190.20 (5)
O5—C13—H13B108.5O2i—Ni1—O186.79 (4)
C14—C13—H13B108.5N1—Ni1—O391.14 (5)
H13A—C13—H13B107.5O2—Ni1—O387.24 (4)
O6—C14—C13112.1 (5)N2—Ni1—O395.21 (5)
O6—C14—H14B109.2O2i—Ni1—O387.43 (4)
C13—C14—H14B109.2O1—Ni1—O3173.88 (4)
N2—C1—C2—C3173.41 (16)Ni1—N1—C12—C11−49.5 (8)
N2—C1—C2—C7−8.3 (3)C10—C11—C12—N176.3 (8)
C7—C2—C3—C4−0.5 (2)C2—C7—O2—Ni118.74 (17)
C1—C2—C3—C4177.90 (14)C6—C7—O2—Ni1−163.04 (9)
C2—C3—C4—C5−3.0 (2)C2—C7—O2—Ni1i161.14 (9)
C2—C3—C4—C9178.42 (15)C6—C7—O2—Ni1i−20.64 (17)
C3—C4—C5—C63.5 (2)C8i—N1—Ni1—N2−165.19 (14)
C9—C4—C5—C6−177.85 (15)O5—N1—Ni1—N227.8 (3)
C4—C5—C6—C7−0.6 (2)C12—N1—Ni1—N29.1 (4)
C4—C5—C6—C8−176.51 (14)C8i—N1—Ni1—O2i17.70 (14)
C3—C2—C7—O2−178.27 (13)O5—N1—Ni1—O2i−149.3 (3)
C1—C2—C7—O23.5 (2)C12—N1—Ni1—O2i−168.0 (4)
C3—C2—C7—C63.43 (19)C8i—N1—Ni1—O1104.47 (14)
C1—C2—C7—C6−174.83 (13)O5—N1—Ni1—O1−62.5 (3)
C5—C6—C7—O2178.79 (12)C12—N1—Ni1—O1−81.2 (4)
C8—C6—C7—O2−5.7 (2)C8i—N1—Ni1—O3−69.72 (14)
C5—C6—C7—C2−2.92 (19)O5—N1—Ni1—O3123.3 (3)
C8—C6—C7—C2172.64 (13)C12—N1—Ni1—O3104.6 (4)
C5—C6—C8—N1i−167.56 (16)C7—O2—Ni1—N2−26.78 (11)
C7—C6—C8—N1i16.7 (2)Ni1i—O2—Ni1—N2−176.96 (5)
C2—C1—N2—O6−173.9 (4)C7—O2—Ni1—O2i150.18 (13)
C2—C1—N2—C10176.1 (5)Ni1i—O2—Ni1—O2i0.0
C2—C1—N2—Ni1−9.3 (2)C7—O2—Ni1—O163.42 (11)
C8i—N1—O5—C13105.4 (5)Ni1i—O2—Ni1—O1−86.76 (4)
C12—N1—O5—C137(2)C7—O2—Ni1—O3−122.01 (11)
Ni1—N1—O5—C13−86.3 (6)Ni1i—O2—Ni1—O387.81 (4)
C1—N2—O6—C14−152.8 (5)C1—N2—Ni1—N1−159.75 (13)
C10—N2—O6—C14−12 (3)O6—N2—Ni1—N11.5 (4)
Ni1—N2—O6—C1443.5 (7)C10—N2—Ni1—N114.8 (5)
N1—O5—C13—C1455.4 (7)C1—N2—Ni1—O221.03 (14)
N2—O6—C14—C13−104.3 (5)O6—N2—Ni1—O2−177.7 (4)
O5—C13—C14—O654.2 (6)C10—N2—Ni1—O2−164.4 (5)
C1—N2—C10—C11177.8 (6)C1—N2—Ni1—O1−68.92 (13)
O6—N2—C10—C11135 (4)O6—N2—Ni1—O192.3 (4)
Ni1—N2—C10—C113.0 (11)C10—N2—Ni1—O1105.6 (5)
N2—C10—C11—C12−50.5 (11)C1—N2—Ni1—O3108.22 (13)
C8i—N1—C12—C11125.4 (5)O6—N2—Ni1—O3−90.5 (4)
O5—N1—C12—C11−145 (3)C10—N2—Ni1—O3−77.2 (5)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O3i0.858 (9)2.06 (1)2.8475 (15)152 (1)
O1—H1B···O11ii0.838 (8)2.06 (1)2.8455 (19)155 (2)
O3—H3B···O40.831 (9)1.96 (1)2.766 (2)165 (2)
O3—H3A···O110.846 (9)1.95 (1)2.775 (2)164 (1)
O11—H11A···O8iii0.846 (10)1.97 (1)2.806 (3)170 (3)
O11—H11B···O9iv0.856 (10)2.40 (2)3.127 (5)143 (3)
O11—H11B···O10iv0.856 (10)2.46 (2)3.229 (4)150 (3)
O4—H4A···O7v0.839 (10)2.43 (3)3.137 (5)142 (4)
O4—H4B···O7iii0.831 (10)2.43 (2)3.120 (4)140 (3)
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) −x, −y, −z−1; (iv) x−1, y, z; (v) x−1, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O3i0.858 (9)2.06 (1)2.8475 (15)152 (1)
O1—H1B···O11ii0.838 (8)2.06 (1)2.8455 (19)155 (2)
O3—H3B···O40.831 (9)1.96 (1)2.766 (2)165 (2)
O3—H3A···O110.846 (9)1.95 (1)2.775 (2)164 (1)
O11—H11A···O8iii0.846 (10)1.97 (1)2.806 (3)170 (3)
O11—H11B···O9iv0.856 (10)2.40 (2)3.127 (5)143 (3)
O11—H11B···O10iv0.856 (10)2.46 (2)3.229 (4)150 (3)
O4—H4A···O7v0.839 (10)2.43 (3)3.137 (5)142 (4)
O4—H4B···O7iii0.831 (10)2.43 (2)3.120 (4)140 (3)
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) −x, −y, −z−1; (iv) x−1, y, z; (v) x−1, y−1, z.
Acknowledgements top

The authors acknowledge DST-FIST (Government of India) for providing financial assistance to the Department of Inorganic Chemistry.

references
References top

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.

Black, D., Blake, A. J., Dancey, K. P., Harrison, A., McPartlin, M., Parsons, S., Tasker, P. A., Whittaker, G. & Schroder, M. (1998). J. Chem. Soc. Dalton Trans. pp. 3953–3960.

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Bruker (2004). APEX2 and SAINT-Plus (Version 7.06a). Bruker AXS Inc., Madison, Wisconsin, USA.

Dixon, D. W. & Weiss, R. H. (1984). J. Org. Chem. 49, 4487–4494.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Hong, Z., Zheng, P., Zhi-quan, P., Bo, L., Xue-lei, H. & Yong-qiong, L. (2005). J. Coord. Chem. 58, 443–451.

Krishnapriya, K. R. & Kandaswamy, M. (2005). Polyhedron, 24, 113–120.

Lacroix, P. G. (2001). Eur. J. Inorg. Chem. pp. 339–348.

Mckenzie, C. J. & Robson, R. (1988). J. Chem. Soc. Chem. Commun. pp. 112–114.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Tsou, T.-T., Loots, M. & Halpern, J. (1982). J. Am. Chem. Soc. 104, 623–624.

Verani, C. N., Renschler, E., Weyhermiiller, T., Bill, E. & Chaudhuri, P. (2000). J. Chem. Soc. Dalton Trans. pp. 251–258.