{6,6′-Dieth­oxy-2,2′-[ethyl­enebis(nitrilo­methyl­idyne)]diphenolato}nickel(II) monohydrate

Xie, H.

doi:10.1107/S1600536808039822

metal-organic compounds

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Volume 64| Part 12| December 2008| Page m1638

doi:10.1107/S1600536808039822

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{6,6′-Diethoxy-2,2′-[ethylenebis(nitrilomethylidyne)]diphenolato}nickel(II) monohydrate

Hai Xie ^a ^*

^aCollege of Chemistry & Chemical Engineering, Shanxi Datong University, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: xhtgao@126.com

(Received 20 November 2008; accepted 25 November 2008; online 29 November 2008)

In the title compound, [Ni(C₂₀H₂₂N₂O₄)]·H₂O, the Ni^II ion and the water molecule are located on a twofold rotation axis. The Ni ion is coordinated by two N [Ni—N = 1.8462 (18) Å] and two O [Ni—O = 1.8645 (14) Å] atoms in a distorted square-planar geometry. The water molecule and the Ni complex molecule are paired via O—H⋯O hydrogen bonds.

Related literature

For details of the synthesis, see Mohanta et al. (2002 ). For a related crystal structure, see Yu (2006 ). For general background, see: Ghosh et al. (2006 ); Samanta et al. (2007 ); Singh et al. (2007 ); Yu et al. (2007 ).

Experimental

Crystal data

[Ni(C₂₀H₂₂N₂O₄)]·H₂O
M_r = 431.12
Orthorhombic, P b c n
a = 12.8401 (8) Å
b = 19.6133 (12) Å
c = 7.5853 (5) Å
V = 1910.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 273 (2) K
0.15 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.858, T_max = 0.893
8741 measured reflections
1676 independent reflections
1381 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.04
1676 reflections
129 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	2.10	2.8158 (15)	147

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039822/cv2487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039822/cv2487Isup2.hkl

checkCIF report

Comment top

Schiff-bases have played an important role in the development of coordination chemistry as they readily form stable complexes with most of the transition metals, in which some could exhibit interesting properties (Yu et al., 2007; Ghosh et al., 2006; Singh et al., 2007; Samanta et al., 2007). Herein we report a new Ni^II complex based on the tetradentate Schiff-base ligand N,N'-ethylenebis(3-ethoxysalicylaldimine).

The geometry and labeling scheme for the title compound are depicted in Figure 1. The coordination sphere for the Ni^II ion in the title complex is a slightly distorted square planar, in which the four positions are occupied by two N and two O atoms of the Schiff-base ligand. The mean deviation from the plane formed by the two N atoms, two O atoms and the Ni ion is only 0.025 Å. The bond lengths of Ni—N and Ni—O are 1.8462 (18) and 1.8645 (14) /A%, respectively, which are consistant with the corresponding distances in 6,6'-dimethoxy-2,2'-(ethane-1,2-diylbis(nitrilomethylidyne)diphenolato)- nickel(II) (Yu, 2006). The crystalline water molecule and Ni-complex are paired via O—H···.O hydrogen bonds (Table 1, Fig. 1).

Related literature top

For details of the synthesis, see Mohanta et al. (2002). For related crystal structure, see Yu (2006). For general background, see: Ghosh et al. (2006); Samanta et al. (2007); Singh et al. (2007); Yu et al. (2007).

Experimental top

The Schiff base ligand H₂L (H₂L= N,N'-ethylenebis(3-ethoxysalicylaldimine)) was prepared according to the reported method (Mohanta, et al., 2002). The synthesis of the title complex was carried out by reacting Ni(CH₃COO)₂.4H₂O, and H₂L with the molar ratio 1:1 in methanol. After the stirring process was continued for about 30 min at room temperature, the mixture was filtered and the filtrate was allowed to partial evaporate in air for sevral days to produce crystals suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound with the atom-labelling scheme [symmetry code: (A) -x + 1,y,-z + 1/2]. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines denote H-bonds. C-bound H-atoms omitted for clarity.

{6,6'-Diethoxy-2,2'-[ethylenebis(nitrilomethylidyne)]diphenolato}nickel(II) monohydrate top

Crystal data top

[Ni(C₂₀H₂₂N₂O₄)]·H₂O	F(000) = 904
M_r = 431.12	D_x = 1.499 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2n 2ab	Cell parameters from 2990 reflections
a = 12.8401 (8) Å	θ = 3.2–26.5°
b = 19.6133 (12) Å	µ = 1.05 mm⁻¹
c = 7.5853 (5) Å	T = 273 K
V = 1910.3 (2) Å³	Block, red-brown
Z = 4	0.15 × 0.13 × 0.11 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1676 independent reflections
Radiation source: fine-focus sealed tube	1381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→14
T_min = 0.858, T_max = 0.893	k = −16→23
8741 measured reflections	l = −8→8

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0307P)² + 0.9816P] where P = (F_o² + 2F_c²)/3
1676 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ni(C₂₀H₂₂N₂O₄)]·H₂O	V = 1910.3 (2) Å³
M_r = 431.12	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.8401 (8) Å	µ = 1.05 mm⁻¹
b = 19.6133 (12) Å	T = 273 K
c = 7.5853 (5) Å	0.15 × 0.13 × 0.11 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1676 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1381 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.893	R_int = 0.025
8741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
1676 reflections	Δρ_min = −0.41 e Å⁻³
129 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	0.023585 (17)	0.2500	0.03740 (14)
O1	0.41162 (10)	0.09308 (7)	0.17417 (19)	0.0406 (3)
O2	0.32670 (11)	0.20336 (7)	0.03750 (19)	0.0454 (4)
O3	0.5000	0.23474 (14)	0.2500	0.1240 (15)
H3A	0.4599	0.2100	0.1962	0.149*
N1	0.58936 (15)	−0.04538 (8)	0.3175 (2)	0.0457 (5)
C1	0.54450 (19)	−0.11475 (10)	0.3139 (3)	0.0565 (6)
H1A	0.5201	−0.1274	0.4305	0.068*
H1B	0.5969	−0.1474	0.2773	0.068*
C2	0.6841 (2)	−0.03851 (12)	0.3700 (3)	0.0546 (6)
H2	0.7227	−0.0782	0.3842	0.066*
C3	0.31834 (15)	0.08654 (10)	0.1050 (3)	0.0398 (5)
C4	0.26463 (18)	0.02419 (11)	0.0914 (3)	0.0495 (6)
C5	0.1623 (2)	0.02214 (15)	0.0224 (4)	0.0684 (8)
H5	0.1269	−0.0192	0.0171	0.082*
C6	0.1152 (2)	0.07964 (15)	−0.0361 (4)	0.0709 (8)
H6	0.0474	0.0777	−0.0789	0.085*
C7	0.16808 (17)	0.14183 (13)	−0.0323 (3)	0.0550 (6)
H7	0.1361	0.1811	−0.0748	0.066*
C8	0.26779 (16)	0.14498 (11)	0.0345 (3)	0.0427 (5)
C9	0.28968 (19)	0.26143 (11)	−0.0578 (3)	0.0535 (6)
H9A	0.2273	0.2793	−0.0024	0.064*
H9B	0.2727	0.2486	−0.1780	0.064*
C10	0.3732 (2)	0.31410 (12)	−0.0576 (4)	0.0677 (7)
H10A	0.3886	0.3270	0.0616	0.102*
H10B	0.3500	0.3534	−0.1223	0.102*
H10C	0.4347	0.2959	−0.1120	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0425 (2)	0.0303 (2)	0.0394 (2)	0.000	0.01083 (17)	0.000
O1	0.0376 (8)	0.0359 (7)	0.0481 (8)	−0.0025 (6)	0.0007 (7)	−0.0011 (6)
O2	0.0452 (8)	0.0416 (8)	0.0493 (9)	0.0033 (7)	−0.0080 (7)	0.0010 (7)
O3	0.132 (3)	0.0510 (17)	0.189 (4)	0.000	−0.113 (3)	0.000
N1	0.0557 (12)	0.0352 (9)	0.0464 (10)	0.0072 (9)	0.0186 (9)	0.0028 (8)
C1	0.0755 (17)	0.0324 (11)	0.0617 (16)	0.0066 (11)	0.0279 (12)	0.0043 (10)
C2	0.0599 (16)	0.0458 (14)	0.0581 (15)	0.0219 (12)	0.0157 (12)	0.0051 (11)
C3	0.0369 (11)	0.0475 (12)	0.0350 (11)	−0.0042 (9)	0.0075 (9)	−0.0053 (9)
C4	0.0469 (13)	0.0523 (13)	0.0492 (13)	−0.0144 (11)	0.0076 (11)	−0.0052 (11)
C5	0.0511 (15)	0.0715 (18)	0.082 (2)	−0.0239 (13)	0.0014 (14)	−0.0063 (15)
C6	0.0411 (14)	0.092 (2)	0.0792 (19)	−0.0118 (14)	−0.0080 (13)	−0.0123 (17)
C7	0.0427 (13)	0.0687 (16)	0.0538 (14)	0.0038 (12)	−0.0028 (11)	−0.0060 (12)
C8	0.0392 (12)	0.0522 (13)	0.0367 (11)	−0.0006 (10)	0.0034 (9)	−0.0073 (10)
C9	0.0616 (15)	0.0533 (14)	0.0455 (13)	0.0159 (12)	−0.0076 (11)	−0.0005 (11)
C10	0.0848 (19)	0.0510 (14)	0.0673 (17)	0.0039 (14)	−0.0112 (15)	0.0131 (13)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	1.8462 (18)	C3—C8	1.422 (3)
Ni1—N1	1.8462 (18)	C4—C5	1.415 (3)
Ni1—O1ⁱ	1.8645 (14)	C4—C2ⁱ	1.426 (3)
Ni1—O1	1.8645 (14)	C5—C6	1.354 (4)
O1—C3	1.314 (2)	C5—H5	0.9300
O2—C8	1.372 (2)	C6—C7	1.396 (3)
O2—C9	1.431 (2)	C6—H6	0.9300
O3—H3A	0.8168	C7—C8	1.378 (3)
N1—C2	1.287 (3)	C7—H7	0.9300
N1—C1	1.478 (3)	C9—C10	1.489 (3)
C1—C1ⁱ	1.498 (5)	C9—H9A	0.9700
C1—H1A	0.9700	C9—H9B	0.9700
C1—H1B	0.9700	C10—H10A	0.9600
C2—C4ⁱ	1.426 (3)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.408 (3)

N1ⁱ—Ni1—N1	85.77 (12)	C5—C4—C2ⁱ	118.7 (2)
N1ⁱ—Ni1—O1ⁱ	178.06 (7)	C6—C5—C4	120.8 (2)
N1—Ni1—O1ⁱ	94.12 (7)	C6—C5—H5	119.6
N1ⁱ—Ni1—O1	94.12 (7)	C4—C5—H5	119.6
N1—Ni1—O1	178.06 (7)	C5—C6—C7	120.2 (2)
O1ⁱ—Ni1—O1	86.06 (8)	C5—C6—H6	119.9
C3—O1—Ni1	127.35 (13)	C7—C6—H6	119.9
C8—O2—C9	118.21 (16)	C8—C7—C6	119.9 (2)
C2—N1—C1	118.07 (19)	C8—C7—H7	120.1
C2—N1—Ni1	126.62 (16)	C6—C7—H7	120.1
C1—N1—Ni1	115.29 (16)	O2—C8—C7	123.7 (2)
N1—C1—C1ⁱ	108.01 (14)	O2—C8—C3	114.51 (17)
N1—C1—H1A	110.1	C7—C8—C3	121.8 (2)
C1ⁱ—C1—H1A	110.1	O2—C9—C10	108.22 (18)
N1—C1—H1B	110.1	O2—C9—H9A	110.1
C1ⁱ—C1—H1B	110.1	C10—C9—H9A	110.1
H1A—C1—H1B	108.4	O2—C9—H9B	110.1
N1—C2—C4ⁱ	126.2 (2)	C10—C9—H9B	110.1
N1—C2—H2	116.9	H9A—C9—H9B	108.4
C4ⁱ—C2—H2	116.9	C9—C10—H10A	109.5
O1—C3—C4	124.1 (2)	C9—C10—H10B	109.5
O1—C3—C8	119.19 (18)	H10A—C10—H10B	109.5
C4—C3—C8	116.69 (19)	C9—C10—H10C	109.5
C3—C4—C5	120.4 (2)	H10A—C10—H10C	109.5
C3—C4—C2ⁱ	120.5 (2)	H10B—C10—H10C	109.5

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.82	2.38	3.056 (3)	140
O3—H3A···O2	0.82	2.10	2.8158 (15)	147

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₂₂N₂O₄)]·H₂O
M_r	431.12
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	273
a, b, c (Å)	12.8401 (8), 19.6133 (12), 7.5853 (5)
V (Å³)	1910.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.15 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.858, 0.893
No. of measured, independent and observed [I > 2σ(I)] reflections	8741, 1676, 1381
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.072, 1.04
No. of reflections	1676
No. of parameters	129
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.41

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	2.10	2.8158 (15)	147.0

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ghosh, R., Rahaman, S. H., Lin, C. N., Lu, T. H. & Ghosh, B. K. (2006). Polyhedron, 25, 3104–3112. Web of Science CSD CrossRef CAS Google Scholar
Mohanta, S., Lin, H. H., Lee, C. J. & Wei, H. H. (2002). Inorg. Chem. Commun. 5, 585–588. Web of Science CSD CrossRef CAS Google Scholar
Samanta, B., Chakraborty, J., Choudhury, C. R., Dey, S. K., Dey, D. K., Batten, S. R., Jensen, P., Yap, G. P. A. & Mitra, S. (2007). Struct. Chem. 18, 33–41. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, K., Barwa, M. S. & Tyagi, P. (2007). Eur. J. Med. Chem. 42, 394–402. Web of Science CrossRef PubMed CAS Google Scholar
Yu, Y.-Y. (2006). Acta Cryst. E62, m948–m949. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Fan, D. W. & Dong, W. K. (2007). Inorg. Chem. Commun. 10, 401–403. Web of Science CSD CrossRef CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1638

doi:10.1107/S1600536808039822

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

{6,6′-Dieth­­oxy-2,2′-[ethyl­enebis(nitrilo­methyl­­idyne)]diphenolato}nickel(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

{6,6′-Diethoxy-2,2′-[ethylenebis(nitrilomethylidyne)]diphenolato}nickel(II) monohydrate