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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m646–m647.
Published online 2008 April 10. doi:  10.1107/S1600536808009562
PMCID: PMC2961174

Bis{2-meth­oxy-6-[3-(methyl­amino)propyl­imino­meth­yl]phenolato}nickel(II) bis­(perchlorate)

Abstract

The asymmetric unit of the title compound, [Ni(C12H18N2O2)2](ClO4)2, consists of one-half of a centrosymmetric mononuclear Schiff base nickel(II) complex cation and one perchlorate anion. The NiII ion, lying on the inversion center, is coordinated by two N atoms and two O atoms from two Schiff base ligands, forming a square-planar geometry. The crystal packing is stabilized by N—H(...)O hydrogen bonds.

Related literature

For related structures, see: Arıcı et al. (2005 [triangle]); Bian et al. (2004 [triangle]); Chen et al. (2008 [triangle]); Holm (1960 [triangle]); Ma, Gu et al. (2006 [triangle]); Ma, Lv et al. (2006 [triangle]); Ma, Wu et al. (2006 [triangle]); Ma et al. (2005 [triangle]); Skovsgaard et al. (2005 [triangle]); Zhao (2007 [triangle]); Zhu et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m646-scheme1.jpg

Experimental

Crystal data

  • [Ni(C12H18N2O2)2](ClO4)2
  • M r = 702.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m646-efi1.jpg
  • a = 13.557 (5) Å
  • b = 13.302 (5) Å
  • c = 17.371 (7) Å
  • V = 3133 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.85 mm−1
  • T = 298 (2) K
  • 0.33 × 0.28 × 0.27 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.766, T max = 0.802
  • 16728 measured reflections
  • 3276 independent reflections
  • 2125 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.188
  • S = 1.04
  • 3276 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.97 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009562/ci2578sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009562/ci2578Isup2.hkl

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

Acknowledgments

The author acknowledges the Zhoukou Vocational and Technical College for a research grant.

supplementary crystallographic information

Comment

Nickel(II) complexes with Schiff base ligands have been of great interest in coordination chemistry related to molecular structures and catalytical applications (Chen et al., 2008; Holm, 1960; Arıcı et al., 2005). Metal complexes derived from Schiff bases have been widely studied (Ma, Lv et al., 2006; Ma, Gu et al., 2006; Ma, Wu et al., 2006; Ma et al., 2005). However, the complexes derived from the Schiff base ligand 2-methoxy-6-[(3-methylaminopropylimino)methyl]phenol have never been reported. The author reports herein the title mononuclear nickel(II) complex.

The title compound consists of a centrosymmetric nickel(II) complex cation and two perchlorate anions (Fig. 1). The NiII ion, lying on the inversion center, is coordinated by two nitrogen atoms and two oxygen atoms from two Schiff base ligands, giving a square planar geometry. All the bond lengths and angles (Table 1) involving the NiII atom are within normal ranges, and comparable to values observed in other Schiff base nickel(II) complexes (Zhu et al., 2004; Zhao, 2007; Bian et al., 2004; Skovsgaard et al., 2005). The N1—C8—C9—C10 and C9—C10—N2—C11 torsion angles are 55.0 (3) and 2.7 (3)°, respectively. The crystal packing is stabilized by N—H···O hydrogen bonds (Table 2).

Experimental

N-Methylpropane-1,3-diamine (0.5 mmol, 44.0 mg) and 3-methoxysalicylaldehyde (0.5 mmol, 76.0 mg) were dissolved in methanol (30 ml). The mixture was stirred for 1 h to obtain a clear yellow solution. To the solution was added with stirring a methanol solution (20 ml) of nickel(II) perchlorate (0.5 mmol, 192.0 mg). After keeping the resulting solution in air for a few days, red block-shaped crystals were formed.

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C-H = 0.93–0.97 Å, N-H = 0.90 Å, and with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Unlabelled atoms are related to labelled atoms by the symmetry operation (1 - x, 1 - y, 1 - z).

Crystal data

[Ni(C12H18N2O2)2](ClO4)2F000 = 1464
Mr = 702.18Dx = 1.489 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3048 reflections
a = 13.557 (5) Åθ = 2.3–25.3º
b = 13.302 (5) ŵ = 0.86 mm1
c = 17.371 (7) ÅT = 298 (2) K
V = 3133 (2) Å3Block, red
Z = 40.33 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer3276 independent reflections
Radiation source: fine-focus sealed tube2125 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 298(2) Kθmax = 26.6º
ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −8→17
Tmin = 0.766, Tmax = 0.802k = −16→15
16728 measured reflectionsl = −19→21

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055  w = 1/[σ2(Fo2) + (0.0892P)2 + 4.466P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.188(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.97 e Å3
3276 reflectionsΔρmin = −0.55 e Å3
199 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (6)
Secondary atom site location: difference Fourier map

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
Ni10.50000.50000.50000.0412 (3)
Cl10.39978 (9)0.29292 (9)0.63654 (7)0.0623 (4)
O10.5954 (2)0.5558 (2)0.56985 (16)0.0550 (8)
O20.6861 (3)0.7085 (3)0.6382 (2)0.0792 (11)
O30.4646 (5)0.3472 (5)0.5938 (4)0.178 (3)
O40.4518 (5)0.2905 (5)0.7084 (4)0.169 (3)
O50.3852 (5)0.1987 (5)0.6207 (7)0.260 (6)
O60.3118 (3)0.3474 (4)0.6470 (3)0.1112 (15)
N10.6046 (3)0.4103 (3)0.45407 (18)0.0497 (8)
N20.4565 (3)0.4199 (3)0.2818 (2)0.0604 (10)
H2A0.43510.42110.33080.072*
H2B0.43630.36150.26080.072*
C10.7430 (4)0.5058 (3)0.5061 (2)0.0549 (11)
C20.6908 (3)0.5687 (3)0.5551 (2)0.0495 (10)
C30.7427 (4)0.6482 (4)0.5911 (2)0.0586 (11)
C40.8418 (4)0.6607 (4)0.5796 (3)0.0715 (14)
H40.87470.71320.60400.086*
C50.8935 (4)0.5960 (5)0.5320 (4)0.0797 (16)
H50.96110.60440.52510.096*
C60.8456 (4)0.5204 (4)0.4957 (3)0.0715 (15)
H60.88060.47740.46340.086*
C70.6969 (3)0.4249 (3)0.4641 (2)0.0563 (11)
H70.73910.37800.44180.068*
C80.5803 (4)0.3206 (3)0.4076 (3)0.0633 (12)
H8A0.51020.30740.41180.076*
H8B0.61500.26300.42860.076*
C90.6073 (4)0.3317 (4)0.3228 (3)0.0731 (15)
H9A0.67860.33480.31870.088*
H9B0.58580.27160.29590.088*
C100.5648 (4)0.4214 (4)0.2820 (3)0.0713 (14)
H10A0.58740.48230.30720.086*
H10B0.58860.42260.22940.086*
C110.4092 (6)0.5042 (4)0.2391 (4)0.099 (2)
H11A0.43230.56710.25940.149*
H11B0.33890.50020.24500.149*
H11C0.42600.49970.18560.149*
C120.7201 (6)0.8047 (4)0.6537 (4)0.113 (2)
H12A0.77550.80100.68800.169*
H12B0.66840.84330.67710.169*
H12C0.74000.83630.60650.169*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0409 (4)0.0501 (4)0.0326 (4)−0.0002 (3)0.0013 (3)−0.0056 (3)
Cl10.0584 (7)0.0553 (6)0.0733 (8)−0.0012 (5)0.0005 (6)0.0103 (5)
O10.0486 (17)0.073 (2)0.0437 (15)−0.0064 (14)0.0031 (13)−0.0133 (14)
O20.082 (3)0.078 (2)0.078 (2)−0.0215 (19)0.0081 (19)−0.0288 (19)
O30.144 (5)0.192 (6)0.197 (6)0.044 (4)0.085 (5)0.123 (5)
O40.184 (6)0.177 (6)0.146 (5)0.022 (5)−0.090 (5)0.013 (4)
O50.145 (6)0.115 (5)0.519 (17)0.000 (4)−0.079 (7)−0.150 (8)
O60.081 (3)0.119 (4)0.133 (4)0.035 (3)0.008 (3)0.024 (3)
N10.057 (2)0.0515 (19)0.0406 (18)0.0053 (16)−0.0010 (15)−0.0024 (14)
N20.078 (3)0.061 (2)0.0424 (19)−0.008 (2)0.0029 (18)−0.0111 (17)
C10.047 (2)0.069 (3)0.049 (2)0.009 (2)−0.0043 (19)0.009 (2)
C20.046 (2)0.063 (3)0.039 (2)0.0010 (19)−0.0043 (17)0.0042 (18)
C30.062 (3)0.067 (3)0.046 (2)−0.009 (2)−0.004 (2)0.000 (2)
C40.059 (3)0.083 (4)0.072 (3)−0.016 (3)−0.012 (3)0.008 (3)
C50.044 (3)0.100 (4)0.095 (4)−0.006 (3)−0.007 (3)0.010 (4)
C60.047 (3)0.094 (4)0.073 (3)0.012 (3)0.002 (2)0.005 (3)
C70.054 (3)0.066 (3)0.049 (2)0.015 (2)0.000 (2)0.001 (2)
C80.073 (3)0.049 (2)0.069 (3)0.008 (2)−0.004 (2)−0.006 (2)
C90.071 (3)0.083 (4)0.065 (3)0.005 (3)0.004 (2)−0.034 (3)
C100.082 (4)0.082 (4)0.049 (3)−0.019 (3)0.016 (2)−0.019 (2)
C110.140 (6)0.083 (4)0.075 (4)0.011 (4)−0.027 (4)0.002 (3)
C120.159 (7)0.066 (4)0.114 (5)−0.024 (4)0.037 (5)0.007 (4)

Geometric parameters (Å, °)

Ni1—O1i1.922 (3)C3—C41.369 (7)
Ni1—O11.922 (3)C4—C51.385 (8)
Ni1—N12.018 (3)C4—H40.93
Ni1—N1i2.018 (3)C5—C61.353 (8)
Cl1—O51.298 (6)C5—H50.93
Cl1—O31.358 (5)C6—H60.93
Cl1—O61.408 (4)C7—H70.93
Cl1—O41.434 (5)C8—C91.525 (7)
O1—C21.329 (5)C8—H8A0.97
O2—C31.378 (6)C8—H8B0.97
O2—C121.386 (6)C9—C101.502 (8)
N1—C71.278 (5)C9—H9A0.97
N1—C81.477 (5)C9—H9B0.97
N2—C101.469 (7)C10—H10A0.97
N2—C111.489 (6)C10—H10B0.97
N2—H2A0.90C11—H11A0.96
N2—H2B0.90C11—H11B0.96
C1—C21.389 (6)C11—H11C0.96
C1—C61.416 (7)C12—H12A0.96
C1—C71.443 (6)C12—H12B0.96
C2—C31.416 (6)C12—H12C0.96
O1i—Ni1—O1180C4—C5—H5120.1
O1i—Ni1—N189.70 (13)C5—C6—C1120.9 (5)
O1—Ni1—N190.30 (14)C5—C6—H6119.5
O1i—Ni1—N1i90.30 (14)C1—C6—H6119.5
O1—Ni1—N1i89.70 (13)N1—C7—C1127.3 (4)
N1—Ni1—N1i180N1—C7—H7116.3
O5—Cl1—O3119.7 (6)C1—C7—H7116.3
O5—Cl1—O6113.3 (4)N1—C8—C9113.3 (4)
O3—Cl1—O6110.2 (3)N1—C8—H8A108.9
O5—Cl1—O4103.7 (6)C9—C8—H8A108.9
O3—Cl1—O499.8 (5)N1—C8—H8B108.9
O6—Cl1—O4108.4 (4)C9—C8—H8B108.9
C2—O1—Ni1125.7 (2)H8A—C8—H8B107.7
C3—O2—C12117.8 (4)C10—C9—C8116.1 (4)
C7—N1—C8114.5 (4)C10—C9—H9A108.3
C7—N1—Ni1123.0 (3)C8—C9—H9A108.3
C8—N1—Ni1122.5 (3)C10—C9—H9B108.3
C10—N2—C11114.9 (5)C8—C9—H9B108.3
C10—N2—H2A108.5H9A—C9—H9B107.4
C11—N2—H2A108.5N2—C10—C9111.9 (4)
C10—N2—H2B108.5N2—C10—H10A109.2
C11—N2—H2B108.5C9—C10—H10A109.2
H2A—N2—H2B107.5N2—C10—H10B109.2
C2—C1—C6119.8 (4)C9—C10—H10B109.2
C2—C1—C7122.6 (4)H10A—C10—H10B107.9
C6—C1—C7117.6 (4)N2—C11—H11A109.5
O1—C2—C1122.4 (4)N2—C11—H11B109.5
O1—C2—C3119.7 (4)H11A—C11—H11B109.5
C1—C2—C3117.9 (4)N2—C11—H11C109.5
C4—C3—O2124.2 (4)H11A—C11—H11C109.5
C4—C3—C2120.9 (5)H11B—C11—H11C109.5
O2—C3—C2114.8 (4)O2—C12—H12A109.5
C3—C4—C5120.6 (5)O2—C12—H12B109.5
C3—C4—H4119.7H12A—C12—H12B109.5
C5—C4—H4119.7O2—C12—H12C109.5
C6—C5—C4119.8 (5)H12A—C12—H12C109.5
C6—C5—H5120.1H12B—C12—H12C109.5

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.901.802.691 (4)170
N2—H2A···O2i0.902.442.929 (5)114
N2—H2B···O4ii0.902.233.075 (8)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2578).

References

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