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

He, Y.-T.

doi:10.1107/S1600536808009562

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m646-m647

doi:10.1107/S1600536808009562

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

Yin-Ting He ^a ^*

^aZhoukou Vocational and Technical College, Zhoukou Henan 466600, People's Republic of China
^*Correspondence e-mail: yinting_he@163.com

(Received 7 April 2008; accepted 7 April 2008; online 10 April 2008)

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 Ni^II 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 ); Bian et al. (2004 ); Chen et al. (2008 ); Holm (1960 ); Ma, Gu et al. (2006 ); Ma, Lv et al. (2006 ); Ma, Wu et al. (2006 ); Ma et al. (2005 ); Skovsgaard et al. (2005 ); Zhao (2007 ); Zhu et al. (2004 ).

Experimental

Crystal data

[Ni(C₁₂H₁₈N₂O₂)₂](ClO₄)₂
M_r = 702.18
Orthorhombic, P b c a
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 ) 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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.188
S = 1.04
3276 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.922 (3)
Ni1—N1	2.018 (3)

O1ⁱ—Ni1—O1	180
O1—Ni1—N1	90.30 (14)
O1—Ni1—N1ⁱ	89.70 (13)
N1—Ni1—N1ⁱ	180
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.90	1.80	2.691 (4)	170
N2—H2A⋯O2ⁱ	0.90	2.44	2.929 (5)	114
N2—H2B⋯O4ⁱⁱ	0.90	2.23	3.075 (8)	157
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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: SHELXL97.

Supporting information

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

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

checkCIF report

Comment top

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 Ni^II 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 Ni^II 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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top

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).

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

Crystal data top

[Ni(C₁₂H₁₈N₂O₂)₂](ClO₄)₂	F(000) = 1464
M_r = 702.18	D_x = 1.489 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3048 reflections
a = 13.557 (5) Å	θ = 2.3–25.3°
b = 13.302 (5) Å	µ = 0.86 mm⁻¹
c = 17.371 (7) Å	T = 298 K
V = 3133 (2) Å³	Block, red
Z = 4	0.33 × 0.28 × 0.27 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3276 independent reflections
Radiation source: fine-focus sealed tube	2125 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 26.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→17
T_min = 0.766, T_max = 0.802	k = −16→15
16728 measured reflections	l = −19→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.0892P)² + 4.466P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3276 reflections	Δρ_max = 0.97 e Å⁻³
199 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (6)

Crystal data top

[Ni(C₁₂H₁₈N₂O₂)₂](ClO₄)₂	V = 3133 (2) Å³
M_r = 702.18	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.557 (5) Å	µ = 0.86 mm⁻¹
b = 13.302 (5) Å	T = 298 K
c = 17.371 (7) Å	0.33 × 0.28 × 0.27 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3276 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2125 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.802	R_int = 0.042
16728 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	Δρ_max = 0.97 e Å⁻³
3276 reflections	Δρ_min = −0.55 e Å⁻³
199 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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.0412 (3)
Cl1	0.39978 (9)	0.29292 (9)	0.63654 (7)	0.0623 (4)
O1	0.5954 (2)	0.5558 (2)	0.56985 (16)	0.0550 (8)
O2	0.6861 (3)	0.7085 (3)	0.6382 (2)	0.0792 (11)
O3	0.4646 (5)	0.3472 (5)	0.5938 (4)	0.178 (3)
O4	0.4518 (5)	0.2905 (5)	0.7084 (4)	0.169 (3)
O5	0.3852 (5)	0.1987 (5)	0.6207 (7)	0.260 (6)
O6	0.3118 (3)	0.3474 (4)	0.6470 (3)	0.1112 (15)
N1	0.6046 (3)	0.4103 (3)	0.45407 (18)	0.0497 (8)
N2	0.4565 (3)	0.4199 (3)	0.2818 (2)	0.0604 (10)
H2A	0.4351	0.4211	0.3308	0.072*
H2B	0.4363	0.3615	0.2608	0.072*
C1	0.7430 (4)	0.5058 (3)	0.5061 (2)	0.0549 (11)
C2	0.6908 (3)	0.5687 (3)	0.5551 (2)	0.0495 (10)
C3	0.7427 (4)	0.6482 (4)	0.5911 (2)	0.0586 (11)
C4	0.8418 (4)	0.6607 (4)	0.5796 (3)	0.0715 (14)
H4	0.8747	0.7132	0.6040	0.086*
C5	0.8935 (4)	0.5960 (5)	0.5320 (4)	0.0797 (16)
H5	0.9611	0.6044	0.5251	0.096*
C6	0.8456 (4)	0.5204 (4)	0.4957 (3)	0.0715 (15)
H6	0.8806	0.4774	0.4634	0.086*
C7	0.6969 (3)	0.4249 (3)	0.4641 (2)	0.0563 (11)
H7	0.7391	0.3780	0.4418	0.068*
C8	0.5803 (4)	0.3206 (3)	0.4076 (3)	0.0633 (12)
H8A	0.5102	0.3074	0.4118	0.076*
H8B	0.6150	0.2630	0.4286	0.076*
C9	0.6073 (4)	0.3317 (4)	0.3228 (3)	0.0731 (15)
H9A	0.6786	0.3348	0.3187	0.088*
H9B	0.5858	0.2716	0.2959	0.088*
C10	0.5648 (4)	0.4214 (4)	0.2820 (3)	0.0713 (14)
H10A	0.5874	0.4823	0.3072	0.086*
H10B	0.5886	0.4226	0.2294	0.086*
C11	0.4092 (6)	0.5042 (4)	0.2391 (4)	0.099 (2)
H11A	0.4323	0.5671	0.2594	0.149*
H11B	0.3389	0.5002	0.2450	0.149*
H11C	0.4260	0.4997	0.1856	0.149*
C12	0.7201 (6)	0.8047 (4)	0.6537 (4)	0.113 (2)
H12A	0.7755	0.8010	0.6880	0.169*
H12B	0.6684	0.8433	0.6771	0.169*
H12C	0.7400	0.8363	0.6065	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0409 (4)	0.0501 (4)	0.0326 (4)	−0.0002 (3)	0.0013 (3)	−0.0056 (3)
Cl1	0.0584 (7)	0.0553 (6)	0.0733 (8)	−0.0012 (5)	0.0005 (6)	0.0103 (5)
O1	0.0486 (17)	0.073 (2)	0.0437 (15)	−0.0064 (14)	0.0031 (13)	−0.0133 (14)
O2	0.082 (3)	0.078 (2)	0.078 (2)	−0.0215 (19)	0.0081 (19)	−0.0288 (19)
O3	0.144 (5)	0.192 (6)	0.197 (6)	0.044 (4)	0.085 (5)	0.123 (5)
O4	0.184 (6)	0.177 (6)	0.146 (5)	0.022 (5)	−0.090 (5)	0.013 (4)
O5	0.145 (6)	0.115 (5)	0.519 (17)	0.000 (4)	−0.079 (7)	−0.150 (8)
O6	0.081 (3)	0.119 (4)	0.133 (4)	0.035 (3)	0.008 (3)	0.024 (3)
N1	0.057 (2)	0.0515 (19)	0.0406 (18)	0.0053 (16)	−0.0010 (15)	−0.0024 (14)
N2	0.078 (3)	0.061 (2)	0.0424 (19)	−0.008 (2)	0.0029 (18)	−0.0111 (17)
C1	0.047 (2)	0.069 (3)	0.049 (2)	0.009 (2)	−0.0043 (19)	0.009 (2)
C2	0.046 (2)	0.063 (3)	0.039 (2)	0.0010 (19)	−0.0043 (17)	0.0042 (18)
C3	0.062 (3)	0.067 (3)	0.046 (2)	−0.009 (2)	−0.004 (2)	0.000 (2)
C4	0.059 (3)	0.083 (4)	0.072 (3)	−0.016 (3)	−0.012 (3)	0.008 (3)
C5	0.044 (3)	0.100 (4)	0.095 (4)	−0.006 (3)	−0.007 (3)	0.010 (4)
C6	0.047 (3)	0.094 (4)	0.073 (3)	0.012 (3)	0.002 (2)	0.005 (3)
C7	0.054 (3)	0.066 (3)	0.049 (2)	0.015 (2)	0.000 (2)	0.001 (2)
C8	0.073 (3)	0.049 (2)	0.069 (3)	0.008 (2)	−0.004 (2)	−0.006 (2)
C9	0.071 (3)	0.083 (4)	0.065 (3)	0.005 (3)	0.004 (2)	−0.034 (3)
C10	0.082 (4)	0.082 (4)	0.049 (3)	−0.019 (3)	0.016 (2)	−0.019 (2)
C11	0.140 (6)	0.083 (4)	0.075 (4)	0.011 (4)	−0.027 (4)	0.002 (3)
C12	0.159 (7)	0.066 (4)	0.114 (5)	−0.024 (4)	0.037 (5)	0.007 (4)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.922 (3)	C3—C4	1.369 (7)
Ni1—O1	1.922 (3)	C4—C5	1.385 (8)
Ni1—N1	2.018 (3)	C4—H4	0.93
Ni1—N1ⁱ	2.018 (3)	C5—C6	1.353 (8)
Cl1—O5	1.298 (6)	C5—H5	0.93
Cl1—O3	1.358 (5)	C6—H6	0.93
Cl1—O6	1.408 (4)	C7—H7	0.93
Cl1—O4	1.434 (5)	C8—C9	1.525 (7)
O1—C2	1.329 (5)	C8—H8A	0.97
O2—C3	1.378 (6)	C8—H8B	0.97
O2—C12	1.386 (6)	C9—C10	1.502 (8)
N1—C7	1.278 (5)	C9—H9A	0.97
N1—C8	1.477 (5)	C9—H9B	0.97
N2—C10	1.469 (7)	C10—H10A	0.97
N2—C11	1.489 (6)	C10—H10B	0.97
N2—H2A	0.90	C11—H11A	0.96
N2—H2B	0.90	C11—H11B	0.96
C1—C2	1.389 (6)	C11—H11C	0.96
C1—C6	1.416 (7)	C12—H12A	0.96
C1—C7	1.443 (6)	C12—H12B	0.96
C2—C3	1.416 (6)	C12—H12C	0.96

O1ⁱ—Ni1—O1	180	C4—C5—H5	120.1
O1ⁱ—Ni1—N1	89.70 (13)	C5—C6—C1	120.9 (5)
O1—Ni1—N1	90.30 (14)	C5—C6—H6	119.5
O1ⁱ—Ni1—N1ⁱ	90.30 (14)	C1—C6—H6	119.5
O1—Ni1—N1ⁱ	89.70 (13)	N1—C7—C1	127.3 (4)
N1—Ni1—N1ⁱ	180	N1—C7—H7	116.3
O5—Cl1—O3	119.7 (6)	C1—C7—H7	116.3
O5—Cl1—O6	113.3 (4)	N1—C8—C9	113.3 (4)
O3—Cl1—O6	110.2 (3)	N1—C8—H8A	108.9
O5—Cl1—O4	103.7 (6)	C9—C8—H8A	108.9
O3—Cl1—O4	99.8 (5)	N1—C8—H8B	108.9
O6—Cl1—O4	108.4 (4)	C9—C8—H8B	108.9
C2—O1—Ni1	125.7 (2)	H8A—C8—H8B	107.7
C3—O2—C12	117.8 (4)	C10—C9—C8	116.1 (4)
C7—N1—C8	114.5 (4)	C10—C9—H9A	108.3
C7—N1—Ni1	123.0 (3)	C8—C9—H9A	108.3
C8—N1—Ni1	122.5 (3)	C10—C9—H9B	108.3
C10—N2—C11	114.9 (5)	C8—C9—H9B	108.3
C10—N2—H2A	108.5	H9A—C9—H9B	107.4
C11—N2—H2A	108.5	N2—C10—C9	111.9 (4)
C10—N2—H2B	108.5	N2—C10—H10A	109.2
C11—N2—H2B	108.5	C9—C10—H10A	109.2
H2A—N2—H2B	107.5	N2—C10—H10B	109.2
C2—C1—C6	119.8 (4)	C9—C10—H10B	109.2
C2—C1—C7	122.6 (4)	H10A—C10—H10B	107.9
C6—C1—C7	117.6 (4)	N2—C11—H11A	109.5
O1—C2—C1	122.4 (4)	N2—C11—H11B	109.5
O1—C2—C3	119.7 (4)	H11A—C11—H11B	109.5
C1—C2—C3	117.9 (4)	N2—C11—H11C	109.5
C4—C3—O2	124.2 (4)	H11A—C11—H11C	109.5
C4—C3—C2	120.9 (5)	H11B—C11—H11C	109.5
O2—C3—C2	114.8 (4)	O2—C12—H12A	109.5
C3—C4—C5	120.6 (5)	O2—C12—H12B	109.5
C3—C4—H4	119.7	H12A—C12—H12B	109.5
C5—C4—H4	119.7	O2—C12—H12C	109.5
C6—C5—C4	119.8 (5)	H12A—C12—H12C	109.5
C6—C5—H5	120.1	H12B—C12—H12C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.90	1.80	2.691 (4)	170
N2—H2A···O2ⁱ	0.90	2.44	2.929 (5)	114
N2—H2B···O4ⁱⁱ	0.90	2.23	3.075 (8)	157

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₈N₂O₂)₂](ClO₄)₂
M_r	702.18
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.557 (5), 13.302 (5), 17.371 (7)
V (Å³)	3133 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.33 × 0.28 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.766, 0.802
No. of measured, independent and observed [I > 2σ(I)] reflections	16728, 3276, 2125
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.188, 1.04
No. of reflections	3276
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.55

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	1.922 (3)	Ni1—N1	2.018 (3)

O1ⁱ—Ni1—O1	180	O1—Ni1—N1ⁱ	89.70 (13)
O1—Ni1—N1	90.30 (14)	N1—Ni1—N1ⁱ	180

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.90	1.80	2.691 (4)	170
N2—H2A···O2ⁱ	0.90	2.44	2.929 (5)	114
N2—H2B···O4ⁱⁱ	0.90	2.23	3.075 (8)	157

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

Acknowledgements

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

References

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Volume 64| Part 5| May 2008| Pages m646-m647

doi:10.1107/S1600536808009562

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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