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Acta Cryst. (2007). E63, m2129    [ doi:10.1107/S1600536807033442 ]

Aqua(2,2'-bipyridine)(2-formyl-4,6-dinitrophenolato)nickel(II) perchlorate

F. Zhong, Q.-Y. Luo, D.-P. Duan, Q. Wang and S.-M. Ying

Abstract top

In the title complex, [Ni(C7H3N2O6)(C10H8N2)(H2O)]ClO4, the NiII ion adopts a distorted square-pyramidal coordination geometry, with the coordinated water molecule occupying the apical position. The NiII complex cation is linked to the ClO4- anion by O-H...O hydrogen bonding.

Comment top

Synthesis of transition metal complexes with aldehyde groups has been a subject of considerable importance (Huang & Gladysz, 1998). A series complexes of this type has been report (Li & Chen, 2006; Das et al., 1997; Wang et al., 2001). Recent years, research effort has been devoted to the study of substituted bis(salicylaldehydato)nickel(II) complexes because of their catalytic activity in the dimerization of propylene and in olefin oligomerization when used together with an aluminium co-catalyst and/or phosphine ligand (Wu & Lu, 2003). In order to study the structure of bis(salicylaldehydato)nickel(II) complexes, We reported here the synthesis and crystal structure of a new nickle(II) complex.

As shown in Fig. 1, the title compound contains one Ni(II) ion, one 2-formyl-4,6-dinitrophenolate (L) ligand, one 2,2'-bipyridine, one coordinated water molecules and one ClO4− anion. This compound exhibits a mononuclear structure. The Ni atom is five coordinated by two O atoms from the L ligand, two N atoms from the bidentate ligand (bipy) and one O atom from the coordinated water molecule, forming a slightly distorted square pyramidal geometry, with N1, N2, O10, O1 in the basal plane and O1W in the axial position. The bond lengths of Ni—O or Ni—N are similar to those reported for other Ni complexes (Das et al., 1997). The [Ni(2,2'-bipy)(L)(H2O)]+ cations and the ClO4− anions are interlinked into a supramolecular structure by the O···O hydrogen bond which exists between the oxygen atoms of the water molecule and the oxygen atoms of the perchlorate (Fig. 2).

Related literature top

For general background, see Huang & Gladysz (1988); Li & Chen (2006); Wang et al. (2001); Wu & Lu (2003). For a related structure, see Das et al. (1997).

Experimental top

An aqueous solution (10 ml) nickel perchloride (0.46 g, 1 mmol) was added dropwise inyo an ethanol-water solution of 2-hydroxy-3,5-dinitrobenzaldehyde (0.21 g, 1 mmol). Then an ethanol solution (3 ml) of 2,2'-bipy (0.16 g, 1 mmol) was mixed with the above solution. The mixture was stirred for 1 h at room temperature. The green crystal was separated by slow evaporation of the solvent at room temperature over a period of about two weeks.

Refinement top

Water H atoms ere located in a difference Fourier map and refined as riding in their as-found relative positions with Uiso(H) = 1.5Ueq(O). Aromatic H atoms were generated geometrically with C—H = 0.93 Å and refined in the riding-model approximation, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Projection of the title compound viewed down the c axis.
Aqua(2,2'-bipyridine)(2-formyl-4,6-dinitrophenolato)nickel(II) perchlorate top
Crystal data top
[Ni(C7H3N2O6)(C10H8N2)(H2O)]ClO4F(000) = 1104
Mr = 543.47Dx = 1.734 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3862 reflections
a = 7.4481 (3) Åθ = 2.0–25.5°
b = 24.1832 (9) ŵ = 1.13 mm−1
c = 11.6691 (4) ÅT = 293 K
β = 98.021 (2)°Block, green
V = 2081.26 (13) Å30.28 × 0.22 × 0.16 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer		3862 independent reflections
Radiation source: fine-focus sealed tube2976 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		h = −8→9
Tmin = 0.742, Tmax = 0.840k = −25→29
11140 measured reflectionsl = −13→14
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0899P)2 + 1.1617P]
where P = (Fo2 + 2Fc2)/3
3862 reflections(Δ/σ)max = 0.002
307 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
[Ni(C7H3N2O6)(C10H8N2)(H2O)]ClO4V = 2081.26 (13) Å3
Mr = 543.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.4481 (3) ŵ = 1.13 mm−1
b = 24.1832 (9) ÅT = 293 K
c = 11.6691 (4) Å0.28 × 0.22 × 0.16 mm
β = 98.021 (2)°
Data collection top
Bruker APEX area-detector
diffractometer		3862 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		2976 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 0.840Rint = 0.036
11140 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.161Δρmax = 0.53 e Å−3
S = 1.05Δρmin = −0.42 e Å−3
3862 reflectionsAbsolute structure: ?
307 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Ni10.38844 (6)0.12807 (2)0.36590 (4)0.0515 (2)
Cl10.72075 (18)0.29702 (6)0.25988 (10)0.0786 (4)
N10.5932 (4)0.10590 (14)0.2851 (3)0.0552 (8)
N20.3009 (5)0.16174 (13)0.2129 (3)0.0602 (8)
N30.6769 (5)0.02080 (16)0.6778 (3)0.0671 (9)
N40.2015 (7)0.05604 (18)0.9129 (4)0.0847 (12)
O10.4707 (4)0.08100 (12)0.4955 (2)0.0634 (7)
O20.7174 (5)−0.02028 (15)0.7391 (3)0.0905 (10)
O30.7727 (5)0.03745 (18)0.6097 (3)0.1009 (13)
O40.2983 (7)0.03533 (18)0.9933 (3)0.1120 (14)
O50.0433 (7)0.0705 (2)0.9158 (4)0.1288 (17)
O60.8095 (11)0.3113 (3)0.1710 (6)0.206 (3)
O70.7424 (13)0.3400 (3)0.3349 (6)0.223 (4)
O80.5391 (9)0.2903 (3)0.2204 (7)0.212 (4)
O90.7850 (8)0.2486 (3)0.3140 (7)0.181 (3)
O100.1627 (4)0.14491 (14)0.4282 (3)0.0718 (8)
O1W0.5206 (5)0.20274 (14)0.4487 (3)0.0907 (11)
H1W0.57040.20730.51670.136*
H2W0.59650.21810.40590.136*
C10.4103 (5)0.07758 (15)0.5925 (3)0.0510 (8)
C20.5053 (5)0.04762 (16)0.6876 (3)0.0548 (9)
C30.4404 (6)0.04219 (16)0.7917 (3)0.0601 (10)
H30.50720.02300.85240.072*
C40.2758 (6)0.06537 (16)0.8056 (3)0.0603 (10)
C50.1757 (6)0.09459 (16)0.7184 (4)0.0611 (10)
H50.06490.10990.72970.073*
C60.2406 (5)0.10143 (16)0.6121 (3)0.0541 (9)
C70.1301 (6)0.13249 (18)0.5261 (4)0.0667 (11)
H70.02030.14500.54570.080*
C80.7379 (6)0.07741 (19)0.3332 (4)0.0669 (11)
H80.74620.06700.41050.080*
C90.8763 (6)0.0629 (2)0.2709 (5)0.0772 (13)
H90.97650.04320.30550.093*
C100.8616 (7)0.0785 (2)0.1571 (5)0.0804 (14)
H100.95320.06930.11380.096*
C110.7148 (7)0.1070 (2)0.1069 (4)0.0756 (13)
H110.70390.11670.02910.091*
C120.5786 (6)0.12171 (16)0.1738 (4)0.0616 (11)
C130.4126 (6)0.15312 (17)0.1330 (3)0.0618 (10)
C140.3683 (8)0.1739 (2)0.0216 (4)0.0780 (13)
H140.44540.1680−0.03350.094*
C150.2122 (10)0.2028 (2)−0.0067 (4)0.0951 (18)
H150.18250.2171−0.08100.114*
C160.0993 (8)0.2109 (2)0.0742 (5)0.0856 (15)
H16−0.00890.23020.05560.103*
C170.1483 (6)0.18994 (18)0.1844 (4)0.0693 (11)
H170.07220.19570.24010.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0540 (3)0.0636 (3)0.0395 (3)0.0065 (2)0.0162 (2)0.0060 (2)
Cl10.0865 (8)0.0984 (9)0.0533 (6)−0.0131 (7)0.0182 (5)−0.0012 (6)
N10.061 (2)0.0607 (17)0.0473 (18)−0.0045 (16)0.0191 (15)−0.0026 (14)
N20.074 (2)0.0582 (19)0.0496 (18)−0.0063 (17)0.0124 (16)0.0028 (15)
N30.060 (2)0.082 (2)0.060 (2)0.0082 (18)0.0111 (17)0.0163 (18)
N40.115 (4)0.085 (3)0.059 (2)0.011 (3)0.031 (2)0.002 (2)
O10.0602 (16)0.0836 (19)0.0509 (15)0.0152 (14)0.0231 (13)0.0131 (14)
O20.084 (2)0.099 (2)0.091 (2)0.0278 (19)0.0200 (18)0.034 (2)
O30.068 (2)0.143 (3)0.099 (3)0.027 (2)0.036 (2)0.050 (2)
O40.164 (4)0.118 (3)0.059 (2)0.019 (3)0.032 (2)0.018 (2)
O50.138 (4)0.169 (4)0.095 (3)0.036 (3)0.073 (3)0.026 (3)
O60.253 (8)0.236 (7)0.159 (5)−0.084 (6)0.134 (6)−0.007 (5)
O70.321 (10)0.208 (7)0.140 (5)0.025 (7)0.034 (6)−0.081 (5)
O80.131 (5)0.253 (8)0.234 (8)−0.073 (5)−0.039 (5)0.082 (7)
O90.146 (5)0.164 (5)0.243 (7)0.041 (4)0.070 (5)0.066 (5)
O100.0678 (19)0.096 (2)0.0543 (17)0.0221 (16)0.0180 (14)0.0176 (15)
O1W0.129 (3)0.085 (2)0.0584 (19)−0.018 (2)0.0141 (19)−0.0086 (16)
C10.057 (2)0.054 (2)0.045 (2)−0.0015 (16)0.0182 (16)0.0034 (16)
C20.053 (2)0.059 (2)0.054 (2)0.0031 (17)0.0145 (17)0.0046 (17)
C30.074 (3)0.061 (2)0.046 (2)0.001 (2)0.0104 (18)0.0061 (17)
C40.081 (3)0.059 (2)0.045 (2)0.000 (2)0.025 (2)−0.0009 (17)
C50.066 (3)0.063 (2)0.060 (2)0.0050 (19)0.027 (2)−0.0043 (19)
C60.057 (2)0.063 (2)0.045 (2)0.0048 (18)0.0161 (16)0.0024 (16)
C70.062 (3)0.083 (3)0.060 (3)0.016 (2)0.025 (2)0.005 (2)
C80.065 (3)0.080 (3)0.059 (2)0.001 (2)0.021 (2)−0.002 (2)
C90.064 (3)0.086 (3)0.088 (3)0.002 (2)0.035 (2)−0.011 (3)
C100.076 (3)0.088 (3)0.087 (3)−0.009 (3)0.048 (3)−0.019 (3)
C110.093 (4)0.084 (3)0.058 (3)−0.018 (3)0.040 (3)−0.011 (2)
C120.077 (3)0.060 (2)0.051 (2)−0.017 (2)0.023 (2)−0.0082 (18)
C130.083 (3)0.055 (2)0.050 (2)−0.018 (2)0.018 (2)−0.0012 (18)
C140.113 (4)0.076 (3)0.048 (2)−0.012 (3)0.021 (2)0.009 (2)
C150.140 (5)0.090 (4)0.052 (3)−0.014 (4)0.002 (3)0.019 (3)
C160.096 (4)0.077 (3)0.080 (3)0.003 (3)−0.006 (3)0.022 (3)
C170.078 (3)0.069 (3)0.060 (3)0.004 (2)0.006 (2)0.007 (2)
Geometric parameters (Å, °) top
Ni1—O11.924 (3)C2—C31.375 (5)
Ni1—O101.965 (3)C3—C41.378 (6)
Ni1—N11.975 (3)C3—H30.9300
Ni1—N21.988 (3)C4—C51.371 (6)
Ni1—O1W2.213 (3)C5—C61.402 (5)
Cl1—O61.351 (5)C5—H50.9300
Cl1—O71.355 (6)C6—C71.421 (6)
Cl1—O91.384 (6)C7—H70.9300
Cl1—O81.377 (6)C8—C91.386 (6)
N1—C81.335 (5)C8—H80.9300
N1—C121.344 (5)C9—C101.370 (7)
N2—C171.328 (5)C9—H90.9300
N2—C131.349 (5)C10—C111.355 (8)
N3—O31.209 (5)C10—H100.9300
N3—O21.237 (5)C11—C121.410 (6)
N3—C21.452 (5)C11—H110.9300
N4—O41.209 (6)C12—C131.472 (7)
N4—O51.235 (6)C13—C141.390 (6)
N4—C41.455 (5)C14—C151.358 (8)
O1—C11.278 (4)C14—H140.9300
O10—C71.238 (5)C15—C161.364 (8)
O1W—H1W0.8354C15—H150.9300
O1W—H2W0.8863C16—C171.383 (7)
C1—C21.427 (5)C16—H160.9300
C1—C61.437 (5)C17—H170.9300
O1—Ni1—O1091.56 (11)C5—C4—C3121.5 (4)
O1—Ni1—N191.83 (12)C5—C4—N4119.1 (4)
O10—Ni1—N1171.87 (14)C3—C4—N4119.3 (4)
O1—Ni1—N2167.74 (13)C4—C5—C6119.9 (4)
O10—Ni1—N293.27 (13)C4—C5—H5120.0
N1—Ni1—N282.00 (14)C6—C5—H5120.0
O1—Ni1—O1W93.80 (13)C5—C6—C7116.8 (4)
O10—Ni1—O1W91.19 (14)C5—C6—C1120.9 (4)
N1—Ni1—O1W95.96 (14)C7—C6—C1122.4 (3)
N2—Ni1—O1W97.36 (13)O10—C7—C6127.7 (4)
O6—Cl1—O7105.8 (5)O10—C7—H7116.1
O6—Cl1—O9113.1 (5)C6—C7—H7116.1
O7—Cl1—O9110.6 (5)N1—C8—C9121.7 (4)
O6—Cl1—O8109.7 (5)N1—C8—H8119.1
O7—Cl1—O8109.3 (6)C9—C8—H8119.1
O9—Cl1—O8108.3 (4)C10—C9—C8118.3 (5)
C8—N1—C12120.3 (4)C10—C9—H9120.8
C8—N1—Ni1124.9 (3)C8—C9—H9120.8
C12—N1—Ni1114.8 (3)C11—C10—C9120.6 (4)
C17—N2—C13119.7 (4)C11—C10—H10119.7
C17—N2—Ni1126.7 (3)C9—C10—H10119.7
C13—N2—Ni1113.6 (3)C10—C11—C12119.3 (4)
O3—N3—O2122.0 (4)C10—C11—H11120.4
O3—N3—C2120.6 (4)C12—C11—H11120.4
O2—N3—C2117.4 (3)N1—C12—C11119.7 (4)
O4—N4—O5124.4 (5)N1—C12—C13114.2 (4)
O4—N4—C4118.3 (5)C11—C12—C13126.0 (4)
O5—N4—C4117.3 (5)N2—C13—C14120.1 (4)
C1—O1—Ni1128.5 (2)N2—C13—C12115.3 (4)
C7—O10—Ni1125.4 (3)C14—C13—C12124.6 (4)
Ni1—O1W—H1W129.3C15—C14—C13119.8 (5)
Ni1—O1W—H2W112.1C15—C14—H14120.1
H1W—O1W—H2W104.2C13—C14—H14120.1
O1—C1—C2121.6 (3)C16—C15—C14119.7 (5)
O1—C1—C6122.8 (3)C16—C15—H15120.1
C2—C1—C6115.6 (3)C14—C15—H15120.1
C3—C2—C1122.6 (4)C15—C16—C17118.9 (5)
C3—C2—N3116.6 (4)C15—C16—H16120.6
C1—C2—N3120.8 (3)C17—C16—H16120.6
C2—C3—C4119.5 (4)N2—C17—C16121.8 (5)
C2—C3—H3120.2N2—C17—H17119.1
C4—C3—H3120.2C16—C17—H17119.1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O6i0.842.393.149 (8)151
O1W—H1W···O8i0.842.423.159 (9)148
O1W—H2W···O90.892.022.906 (8)175
Symmetry codes: (i) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O6i0.842.393.149 (8)151
O1W—H1W···O8i0.842.423.159 (9)148
O1W—H2W···O90.892.022.906 (8)175
Symmetry codes: (i) x, −y+1/2, z+1/2.
Acknowledgements top

This work was supported by the Science and Technology Foundation of Jiangxi Provincial Department of Education, China [grant No. (2007)316].

references
References top

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