Bis{(E)-2-eth-oxy-6-[2-(ethyl-ammonio)ethyl-iminometh-yl]phenolato}nickel(II) bis(perchlorate).

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C(13)H(20)N(2)O(2))(2)](ClO(4))(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, mol-ecules are linked through inter-molecular 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 = 730.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.04

3363 reflections

207 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.34 e Å−3

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.

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

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

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

[Ni(C13H20N2O2)2](ClO4)2	F000 = 764
Mr = 730.23	Dx = 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 = 2.5–25.4º
b = 8.566 (3) Å	µ = 0.87 mm−1
c = 21.862 (6) Å	T = 298 (2) K
β = 99.068 (4)º	Block, red
V = 1550.8 (9) Å3	0.23 × 0.20 × 0.20 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2770 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.826, Tmax = 0.846	k = −10→10
12509 measured reflections	l = −27→27

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.4599P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3363 reflections	Δρmax = 0.28 e Å−3
207 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .

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) ; (ii) .