Bis{(E)-2-eth­oxy-6-[2-(ethyl­ammonio)ethyl­iminometh­yl]phenolato}nickel(II) bis(perchlorate)

Zhu, X.-W.; Yang, X.-Z.

doi:10.1107/S1600536808023684

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1096-m1097

doi:10.1107/S1600536808023684

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Bis{(E)-2-ethoxy-6-[2-(ethylammonio)ethyliminomethyl]phenolato}nickel(II) bis(perchlorate)

Xue-Wen Zhu ^a ^* and Xu-Zhao Yang ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: xuewen_zhu@126.com

(Received 25 July 2008; accepted 27 July 2008; online 31 July 2008)

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C₁₃H₂₀N₂O₂)₂](ClO₄)₂, the Ni^II atom is four-coordinated by the imine N and phenolate O atoms of the zwitterionic forms of two Schiff base ligands in a square-planar coordination geometry. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the a axis.

Related literature

For background to the chemistry of the Schiff base complexes, see: Ali et al. (2008 ); Biswas et al. (2008 ); Carlsson et al. (2002 , 2004 ); Chen et al. (2008 ); Darensbourg & Frantz (2007 ); Habibi et al. (2007 ); Kawamoto et al. (2008 ); Tomat et al. (2007 ); Wu et al. (2008 ); Yuan et al. (2007 ). For related structures, see: Ma et al. (2008 ); Skovsgaard et al. (2005 ); Zhao (2007 ).

Experimental

Crystal data

[Ni(C₁₃H₂₀N₂O₂)₂](ClO₄)₂
M_r = 730.23
Monoclinic, P 2₁ /n
a = 8.386 (3) Å
b = 8.566 (3) Å
c = 21.862 (6) Å
β = 99.068 (4)°
V = 1550.8 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.826, T_max = 0.846
12509 measured reflections
3363 independent reflections
2770 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.04
3363 reflections
207 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.836 (2)
Ni1—N1	1.910 (2)

O1ⁱ—Ni1—O1	180
O1ⁱ—Ni1—N1	87.67 (7)
O1—Ni1—N1	92.33 (7)
N1ⁱ—Ni1—N1	180
Symmetry code: (i) -x+2, -y+1, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2ⁱ	0.90	2.34	3.013 (3)	131
N2—H2B⋯O1ⁱ	0.90	1.97	2.764 (2)	146
N2—H2A⋯O3	0.90	2.56	3.242 (3)	132
N2—H2A⋯O3ⁱⁱ	0.90	2.13	2.916 (3)	145
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023684/sj2526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023684/sj2526Isup2.hkl

checkCIF report

Comment top

Schiff bases have widely been used as versatile ligands in coordination chemistry (Biswas et al., 2008; Wu et al., 2008; Kawamoto et al., 2008; Ali et al., 2008; Habibi et al., 2007), and their metal complexes are of great interest in many fields (Chen et al., 2008; Yuan et al., 2007; Tomat et al., 2007; Darensbourg & Frantz, 2007). Nickel(II) is present in the active sites of urease (Carlsson et al., 2002, 2004). In this paper, a new nickel(II) complex, (I), Fig. 1, with the Schiff base ligand (E)-2-ethoxy-6-((3-(methylamino)propylimino)methyl)phenol has been synthesized and structurally characterized.

Complex (I) consists of a centrosymmetric mononuclear nickel(II) complex cation and two perchlorate anions. The Ni^II atom in the cation, lies on an inversion centre, with the asymmetric unit made up from one half of the Ni(II) complex and one perchlorate anion. The Ni(II) atom is four-coordinated by two imine N and two phenolate O atoms from two zwitterionic Schiff base ligands in a square-planar coordination geometry. The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in similar nickel(II) Schiff base complexes (Zhao, 2007; Skovsgaard et al., 2005; Ma et al., 2008).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 2), forming chains running along the a axis (Fig. 2).

Related literature top

For background to the chemistry of the Schiff base complexes, see: Ali et al. (2008); Biswas et al. (2008); Carlsson et al. (2002, 2004); Chen et al. (2008); Darensbourg & Frantz (2007); Habibi et al. (2007); Kawamoto et al. (2008); Tomat et al. (2007); Wu et al. (2008); Yuan et al. (2007). For related structures, see: Ma et al. (2008); Skovsgaard et al. (2005); Zhao (2007).

Experimental top

The Schiff base compound was prepared by the condensation of equimolar amounts of 3-ethoxysalicylaldehyde with N-ethylethane-1,2-diamine in a methanol solution. The complex was prepared by the following method. To a methanol solution (5 ml) of Ni(ClO₄)₂.6H₂O (36.6 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (23.6 mg, 0.1 mmol) with stirring. The mixture was stirred for 30 min at room temperature and filtered. Upon keeping the filtrate in air for a few days, red block-shaped crystals formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 30% probability level. Unlabelled atoms are at the symmetry positions 2 - x, 1 - y, - z.
	Fig. 2. The crystal packing of (I), viewed along the c axis.

Bis{(E)-2-Ethoxy-6-[2-(ethylammonio)ethyliminomethyl]phenolato}nickel(II) bis(perchlorate) top

Crystal data top

[Ni(C₁₃H₂₀N₂O₂)₂](ClO₄)₂	F(000) = 764
M_r = 730.23	D_x = 1.564 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3252 reflections
a = 8.386 (3) Å	θ = 2.5–25.4°
b = 8.566 (3) Å	µ = 0.87 mm⁻¹
c = 21.862 (6) Å	T = 298 K
β = 99.068 (4)°	Block, red
V = 1550.8 (9) Å³	0.23 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2770 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.826, T_max = 0.846	k = −10→10
12509 measured reflections	l = −27→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0512P)² + 0.4599P] where P = (F_o² + 2F_c²)/3
3363 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(C₁₃H₂₀N₂O₂)₂](ClO₄)₂	V = 1550.8 (9) Å³
M_r = 730.23	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.386 (3) Å	µ = 0.87 mm⁻¹
b = 8.566 (3) Å	T = 298 K
c = 21.862 (6) Å	0.23 × 0.20 × 0.20 mm
β = 99.068 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3363 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2770 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.846	R_int = 0.041
12509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
3363 reflections	Δρ_min = −0.34 e Å⁻³
207 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	1.0000	0.5000	0.0000	0.02592 (13)
Cl1	0.39043 (7)	0.71469 (7)	0.09059 (3)	0.03882 (17)
O1	1.06353 (18)	0.41002 (18)	0.07614 (7)	0.0333 (4)
O2	1.1550 (2)	0.2125 (2)	0.16406 (8)	0.0451 (4)
O3	0.4539 (3)	0.6169 (2)	0.04665 (9)	0.0624 (6)
O4	0.5075 (2)	0.8315 (2)	0.11174 (9)	0.0547 (5)
O5	0.3594 (3)	0.6194 (2)	0.14062 (9)	0.0652 (6)
O6	0.2480 (3)	0.7874 (3)	0.06108 (13)	0.0790 (7)
N1	0.8973 (2)	0.6697 (2)	0.03503 (8)	0.0272 (4)
N2	0.6314 (2)	0.7051 (2)	−0.07021 (9)	0.0342 (4)
H2A	0.6031	0.6259	−0.0471	0.041*
H2B	0.7139	0.6718	−0.0886	0.041*
C1	0.8960 (3)	0.5512 (3)	0.13583 (10)	0.0307 (5)
C2	1.0022 (3)	0.4303 (3)	0.12705 (9)	0.0281 (5)
C3	1.0473 (3)	0.3232 (3)	0.17637 (10)	0.0322 (5)
C4	0.9828 (3)	0.3361 (3)	0.22998 (10)	0.0385 (6)
H4	1.0109	0.2640	0.2616	0.046*
C5	0.8759 (3)	0.4560 (3)	0.23756 (11)	0.0436 (6)
H5	0.8327	0.4634	0.2741	0.052*
C6	0.8344 (3)	0.5623 (3)	0.19183 (11)	0.0399 (6)
H6	0.7644	0.6433	0.1976	0.048*
C7	0.8602 (3)	0.6692 (3)	0.09004 (10)	0.0308 (5)
H7	0.8036	0.7555	0.1010	0.037*
C8	0.8632 (3)	0.8182 (2)	0.00079 (11)	0.0317 (5)
H8A	0.9308	0.8242	−0.0313	0.038*
H8B	0.8923	0.9044	0.0291	0.038*
C9	0.6887 (3)	0.8363 (3)	−0.02871 (11)	0.0333 (5)
H9A	0.6219	0.8436	0.0036	0.040*
H9B	0.6765	0.9328	−0.0522	0.040*
C10	0.4917 (3)	0.7422 (3)	−0.11922 (13)	0.0487 (7)
H10A	0.5245	0.8215	−0.1464	0.058*
H10B	0.4629	0.6493	−0.1439	0.058*
C11	0.3475 (3)	0.7982 (4)	−0.09446 (14)	0.0568 (8)
H11A	0.3152	0.7211	−0.0670	0.085*
H11B	0.2610	0.8158	−0.1281	0.085*
H11C	0.3728	0.8940	−0.0723	0.085*
C12	1.1937 (3)	0.0850 (3)	0.20663 (12)	0.0465 (6)
H12A	1.2110	0.1255	0.2486	0.056*
H12B	1.2937	0.0372	0.1992	0.056*
C13	1.0661 (5)	−0.0355 (4)	0.2011 (2)	0.0790 (11)
H13A	0.9690	0.0091	0.2116	0.119*
H13B	1.1007	−0.1201	0.2288	0.119*
H13C	1.0458	−0.0737	0.1593	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0286 (2)	0.0257 (2)	0.0236 (2)	0.00323 (15)	0.00463 (15)	0.00429 (15)
Cl1	0.0470 (4)	0.0310 (3)	0.0392 (3)	−0.0058 (2)	0.0091 (3)	−0.0041 (2)
O1	0.0407 (9)	0.0352 (9)	0.0255 (7)	0.0112 (7)	0.0096 (7)	0.0078 (6)
O2	0.0555 (11)	0.0445 (10)	0.0376 (9)	0.0190 (8)	0.0145 (8)	0.0175 (8)
O3	0.1038 (17)	0.0375 (10)	0.0533 (12)	−0.0086 (11)	0.0357 (11)	−0.0095 (9)
O4	0.0541 (12)	0.0456 (11)	0.0639 (13)	−0.0157 (9)	0.0075 (9)	−0.0132 (9)
O5	0.1053 (17)	0.0525 (12)	0.0438 (11)	−0.0208 (12)	0.0300 (11)	−0.0021 (9)
O6	0.0493 (13)	0.0656 (14)	0.116 (2)	−0.0016 (11)	−0.0058 (12)	0.0108 (14)
N1	0.0264 (9)	0.0250 (9)	0.0292 (9)	−0.0002 (7)	0.0015 (7)	0.0020 (7)
N2	0.0319 (10)	0.0294 (10)	0.0408 (11)	0.0026 (8)	0.0038 (8)	−0.0007 (8)
C1	0.0301 (11)	0.0345 (12)	0.0277 (11)	−0.0006 (9)	0.0048 (9)	−0.0003 (9)
C2	0.0290 (11)	0.0310 (11)	0.0244 (10)	−0.0028 (9)	0.0043 (9)	0.0013 (9)
C3	0.0323 (12)	0.0354 (12)	0.0284 (11)	−0.0017 (10)	0.0030 (9)	0.0047 (9)
C4	0.0413 (14)	0.0464 (14)	0.0271 (11)	−0.0036 (11)	0.0034 (10)	0.0079 (10)
C5	0.0465 (15)	0.0580 (16)	0.0288 (12)	0.0011 (13)	0.0132 (11)	0.0006 (11)
C6	0.0391 (13)	0.0466 (14)	0.0356 (13)	0.0061 (11)	0.0107 (10)	−0.0031 (11)
C7	0.0292 (11)	0.0299 (12)	0.0333 (12)	0.0024 (9)	0.0048 (9)	−0.0033 (9)
C8	0.0359 (12)	0.0224 (11)	0.0362 (12)	−0.0029 (9)	0.0033 (10)	0.0010 (9)
C9	0.0374 (13)	0.0232 (11)	0.0387 (12)	0.0043 (9)	0.0042 (10)	0.0019 (9)
C10	0.0474 (15)	0.0519 (16)	0.0429 (14)	−0.0002 (13)	−0.0052 (12)	0.0011 (12)
C11	0.0354 (14)	0.0620 (19)	0.068 (2)	−0.0005 (13)	−0.0059 (13)	0.0023 (15)
C12	0.0508 (16)	0.0441 (15)	0.0445 (14)	0.0123 (12)	0.0072 (12)	0.0191 (12)
C13	0.078 (2)	0.0510 (19)	0.107 (3)	−0.0058 (18)	0.011 (2)	0.010 (2)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.836 (2)	C4—H4	0.9300
Ni1—O1	1.836 (2)	C5—C6	1.357 (4)
Ni1—N1ⁱ	1.910 (2)	C5—H5	0.9300
Ni1—N1	1.910 (2)	C6—H6	0.9300
Cl1—O6	1.410 (2)	C7—H7	0.9300
Cl1—O5	1.421 (2)	C8—C9	1.512 (3)
Cl1—O4	1.4268 (18)	C8—H8A	0.9700
Cl1—O3	1.4384 (19)	C8—H8B	0.9700
O1—C2	1.309 (2)	C9—H9A	0.9700
O2—C3	1.365 (3)	C9—H9B	0.9700
O2—C12	1.439 (3)	C10—C11	1.481 (4)
N1—C7	1.289 (3)	C10—H10A	0.9700
N1—C8	1.481 (3)	C10—H10B	0.9700
N2—C9	1.476 (3)	C11—H11A	0.9600
N2—C10	1.492 (3)	C11—H11B	0.9600
N2—H2A	0.9000	C11—H11C	0.9600
N2—H2B	0.9000	C12—C13	1.478 (4)
C1—C2	1.399 (3)	C12—H12A	0.9700
C1—C6	1.405 (3)	C12—H12B	0.9700
C1—C7	1.421 (3)	C13—H13A	0.9600
C2—C3	1.421 (3)	C13—H13B	0.9600
C3—C4	1.370 (3)	C13—H13C	0.9600
C4—C5	1.390 (4)

O1ⁱ—Ni1—O1	180.0	C1—C6—H6	119.7
O1ⁱ—Ni1—N1ⁱ	92.33 (7)	N1—C7—C1	127.2 (2)
O1—Ni1—N1ⁱ	87.67 (7)	N1—C7—H7	116.4
O1ⁱ—Ni1—N1	87.67 (7)	C1—C7—H7	116.4
O1—Ni1—N1	92.33 (7)	N1—C8—C9	113.63 (18)
N1ⁱ—Ni1—N1	180.0	N1—C8—H8A	108.8
O6—Cl1—O5	111.19 (15)	C9—C8—H8A	108.8
O6—Cl1—O4	109.16 (13)	N1—C8—H8B	108.8
O5—Cl1—O4	110.69 (13)	C9—C8—H8B	108.8
O6—Cl1—O3	109.13 (15)	H8A—C8—H8B	107.7
O5—Cl1—O3	108.15 (12)	N2—C9—C8	112.54 (18)
O4—Cl1—O3	108.46 (13)	N2—C9—H9A	109.1
C2—O1—Ni1	128.20 (14)	C8—C9—H9A	109.1
C3—O2—C12	119.27 (19)	N2—C9—H9B	109.1
C7—N1—C8	114.76 (18)	C8—C9—H9B	109.1
C7—N1—Ni1	124.19 (15)	H9A—C9—H9B	107.8
C8—N1—Ni1	120.95 (14)	C11—C10—N2	113.6 (2)
C9—N2—C10	114.96 (19)	C11—C10—H10A	108.8
C9—N2—H2A	108.5	N2—C10—H10A	108.8
C10—N2—H2A	108.5	C11—C10—H10B	108.8
C9—N2—H2B	108.5	N2—C10—H10B	108.8
C10—N2—H2B	108.5	H10A—C10—H10B	107.7
H2A—N2—H2B	107.5	C10—C11—H11A	109.5
C2—C1—C6	119.9 (2)	C10—C11—H11B	109.5
C2—C1—C7	119.90 (19)	H11A—C11—H11B	109.5
C6—C1—C7	120.0 (2)	C10—C11—H11C	109.5
O1—C2—C1	123.96 (19)	H11A—C11—H11C	109.5
O1—C2—C3	117.8 (2)	H11B—C11—H11C	109.5
C1—C2—C3	118.25 (19)	O2—C12—C13	113.0 (2)
O2—C3—C4	126.0 (2)	O2—C12—H12A	109.0
O2—C3—C2	113.84 (19)	C13—C12—H12A	109.0
C4—C3—C2	120.2 (2)	O2—C12—H12B	109.0
C3—C4—C5	120.7 (2)	C13—C12—H12B	109.0
C3—C4—H4	119.7	H12A—C12—H12B	107.8
C5—C4—H4	119.7	C12—C13—H13A	109.5
C6—C5—C4	120.2 (2)	C12—C13—H13B	109.5
C6—C5—H5	119.9	H13A—C13—H13B	109.5
C4—C5—H5	119.9	C12—C13—H13C	109.5
C5—C6—C1	120.7 (2)	H13A—C13—H13C	109.5
C5—C6—H6	119.7	H13B—C13—H13C	109.5

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.90	2.34	3.013 (3)	131
N2—H2B···O1ⁱ	0.90	1.97	2.764 (2)	146
N2—H2A···O3	0.90	2.56	3.242 (3)	132
N2—H2A···O3ⁱⁱ	0.90	2.13	2.916 (3)	145

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₂₀N₂O₂)₂](ClO₄)₂
M_r	730.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.386 (3), 8.566 (3), 21.862 (6)
β (°)	99.068 (4)
V (Å³)	1550.8 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.826, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	12509, 3363, 2770
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.04
No. of reflections	3363
No. of parameters	207
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.34

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	1.836 (2)	Ni1—N1	1.910 (2)

O1ⁱ—Ni1—O1	180.0	O1—Ni1—N1	92.33 (7)
O1ⁱ—Ni1—N1	87.67 (7)	N1ⁱ—Ni1—N1	180.0

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.90	2.34	3.013 (3)	131
N2—H2B···O1ⁱ	0.90	1.97	2.764 (2)	146
N2—H2A···O3	0.90	2.56	3.242 (3)	132
N2—H2A···O3ⁱⁱ	0.90	2.13	2.916 (3)	145

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

References

Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Carlsson, H., Haukka, M., Bousseksou, A., Latour, J.-M. & Nordlander, E. (2004). Inorg. Chem. 43, 8252–8262. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 64| Part 8| August 2008| Pages m1096-m1097

doi:10.1107/S1600536808023684

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

Bis{(E)-2-eth­­oxy-6-[2-(ethyl­ammonio)ethyl­iminometh­yl]phenolato}nickel(II) bis­(perchlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis{(E)-2-ethoxy-6-[2-(ethylammonio)ethyliminomethyl]phenolato}nickel(II) bis(perchlorate)