Aqua{5,5′-dimethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)

Tang, C.

doi:10.1107/S1600536809039129

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1278

https://doi.org/10.1107/S1600536809039129

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Aqua{5,5′-dimethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)

Chunbao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@126.com

(Received 22 September 2009; accepted 26 September 2009; online 3 October 2009)

The title mononuclear nickel(II) complex, [Ni(C₁₈H₁₈N₂O₄)(H₂O)], possesses crystallographic mirror symmetry. The Ni atom is five-coordinated in a square-pyramidal geometry, with two imine N and two phenolate O atoms of the Schiff base ligand in the square plane, and the water O atom in the axial position. In the crystal, the molecules are linked via intermolecular O—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For related structures, see: Angulo et al. (2001 ); Dey et al. (2004 ); Edison et al. (2004 ); Ramadevi et al. (2005 ); Suh et al. (1996 ); Tang (2009 ).

Experimental

Crystal data

[Ni(C₁₈H₁₈N₂O₄)(H₂O)]
M_r = 403.07
Orthorhombic, P n m a
a = 8.7698 (3) Å
b = 27.0608 (9) Å
c = 7.4731 (2) Å
V = 1773.5 (1) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.823, T_max = 0.832
9937 measured reflections
1978 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.085
S = 1.04
1978 reflections
125 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.847 (10)	1.969 (17)	2.734 (2)	150 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{5\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: https://doi.org/10.1107/S1600536809039129/sj2661sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039129/sj2661Isup2.hkl

checkCIF report

Comment top

Nickel(II) complexes play an important role in both bioinorganic chemistry and coordination chemistry (Suh et al., 1996; Dey et al., 2004; Angulo et al., 2001; Ramadevi et al., 2005; Edison et al., 2004). Recently, the author has reported a nickel(II) complex with a related Schiff base ligand (Tang, 2009). As a continuation of this work, the title mononuclear nickel(II) complex, Fig. 1, is reported here.

The molecule of the title complex possesses crystallographic mirror symmetry. The Ni atom in the complex is five-coordinated by two imine N and two phenolate O atoms of the Schiff base ligand, and by one water O atom, forming a square-pyramidal geometry.

In the crystal structure, the molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming chains along the a axis, as shown in Fig. 2.

Related literature top

For related structures, see: Angulo et al. (2001); Dey et al. (2004); Edison et al. (2004); Ramadevi et al. (2005); Suh et al. (1996); Tang (2009).

Experimental top

4-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg), ethane-1,2-diamine (0.1 mmol, 6.0 mg) and nickel(II) nitrate hexahydrate (0.1 mmol, 29.1 mg) were mixed in a methanol solution (20 ml). The mixture was stirred at room temperature for 30 min to give a green solution. The solution was allowed to stand in air for 5 days, yielding green block-shaped crystals of the title complex.

Structure description top

In the crystal structure, the molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming chains along the a axis, as shown in Fig. 2.

For related structures, see: Angulo et al. (2001); Dey et al. (2004); Edison et al. (2004); Ramadevi et al. (2005); Suh et al. (1996); Tang (2009).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the title complex. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing of the title complex, viewed along the c axis. Intermolecular O—H···O hydrogen bonds are shown as dashed lines.

Aqua{5,5'-dimethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) top

Crystal data top

[Ni(C₁₈H₁₈N₂O₄)(H₂O)]	F(000) = 840
M_r = 403.07	D_x = 1.510 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4326 reflections
a = 8.7698 (3) Å	θ = 2.3–29.2°
b = 27.0608 (9) Å	µ = 1.13 mm⁻¹
c = 7.4731 (2) Å	T = 298 K
V = 1773.5 (1) Å³	Block, green
Z = 4	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area detector diffractometer	1978 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.823, T_max = 0.832	k = −34→32
9937 measured reflections	l = −9→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0327P)² + 1.6368P] where P = (F_o² + 2F_c²)/3
1978 reflections	(Δ/σ)_max = 0.001
125 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ni(C₁₈H₁₈N₂O₄)(H₂O)]	V = 1773.5 (1) Å³
M_r = 403.07	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 8.7698 (3) Å	µ = 1.13 mm⁻¹
b = 27.0608 (9) Å	T = 298 K
c = 7.4731 (2) Å	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area detector diffractometer	1978 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1762 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.832	R_int = 0.023
9937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
1978 reflections	Δρ_min = −0.46 e Å⁻³
125 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	0.04557 (4)	0.2500	1.04045 (5)	0.03460 (13)
N1	0.1893 (2)	0.29806 (9)	0.9426 (3)	0.0540 (5)
O1	−0.10331 (18)	0.30124 (6)	1.0871 (2)	0.0459 (4)
O2	−0.3611 (2)	0.45495 (6)	1.0277 (2)	0.0558 (5)
O3	0.1380 (3)	0.2500	1.3276 (3)	0.0467 (5)
C1	0.0251 (3)	0.36946 (9)	0.9443 (3)	0.0425 (5)
C2	−0.1014 (3)	0.34714 (8)	1.0324 (3)	0.0379 (5)
C3	−0.2323 (3)	0.37628 (8)	1.0615 (3)	0.0412 (5)
H3A	−0.3160	0.3625	1.1197	0.049*
C4	−0.2387 (3)	0.42474 (9)	1.0054 (3)	0.0440 (5)
C5	−0.1154 (3)	0.44666 (9)	0.9178 (3)	0.0535 (6)
H5	−0.1204	0.4793	0.8791	0.064*
C6	0.0129 (3)	0.41896 (9)	0.8904 (3)	0.0519 (6)
H6	0.0958	0.4336	0.8336	0.062*
C7	0.1637 (3)	0.34352 (10)	0.9075 (3)	0.0501 (6)
H7	0.2418	0.3613	0.8532	0.060*
C8	0.3344 (3)	0.27498 (13)	0.8944 (7)	0.1204 (18)
H8A	0.3633	0.2863	0.7760	0.144*
H8B	0.4119	0.2863	0.9774	0.144*
C9	−0.4961 (3)	0.43441 (10)	1.1044 (4)	0.0623 (7)
H9A	−0.5306	0.4073	1.0321	0.093*
H9B	−0.5740	0.4593	1.1096	0.093*
H9C	−0.4743	0.4228	1.2231	0.093*
H3	0.194 (3)	0.2744 (7)	1.355 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02532 (19)	0.0415 (2)	0.0369 (2)	0.000	0.00467 (15)	0.000
N1	0.0328 (10)	0.0682 (14)	0.0611 (13)	−0.0012 (9)	0.0092 (9)	0.0186 (11)
O1	0.0374 (8)	0.0394 (8)	0.0610 (10)	−0.0007 (7)	0.0115 (7)	0.0110 (7)
O2	0.0664 (11)	0.0380 (9)	0.0631 (11)	0.0067 (8)	0.0063 (9)	0.0083 (8)
O3	0.0341 (12)	0.0514 (14)	0.0545 (14)	0.000	−0.0101 (11)	0.000
C1	0.0450 (12)	0.0462 (12)	0.0363 (11)	−0.0125 (10)	0.0011 (9)	0.0016 (10)
C2	0.0390 (11)	0.0389 (11)	0.0360 (10)	−0.0064 (9)	−0.0016 (9)	0.0025 (9)
C3	0.0421 (12)	0.0373 (11)	0.0443 (12)	−0.0050 (9)	0.0034 (10)	0.0022 (9)
C4	0.0555 (14)	0.0387 (12)	0.0378 (11)	−0.0029 (10)	−0.0022 (10)	0.0006 (9)
C5	0.0708 (17)	0.0381 (12)	0.0518 (14)	−0.0100 (12)	0.0048 (13)	0.0077 (11)
C6	0.0578 (15)	0.0502 (14)	0.0478 (13)	−0.0181 (12)	0.0072 (12)	0.0067 (11)
C7	0.0397 (12)	0.0629 (16)	0.0478 (13)	−0.0120 (11)	0.0051 (10)	0.0133 (12)
C8	0.0448 (16)	0.104 (3)	0.212 (5)	0.0225 (16)	0.056 (2)	0.079 (3)
C9	0.0617 (16)	0.0539 (15)	0.0713 (18)	0.0134 (13)	0.0116 (15)	0.0120 (14)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.9363 (16)	C2—C3	1.410 (3)
Ni1—O1	1.9363 (16)	C3—C4	1.378 (3)
Ni1—N1ⁱ	1.953 (2)	C3—H3A	0.9300
Ni1—N1	1.953 (2)	C4—C5	1.396 (3)
Ni1—O3	2.294 (2)	C5—C6	1.367 (4)
N1—C7	1.278 (3)	C5—H5	0.9300
N1—C8	1.463 (3)	C6—H6	0.9300
O1—C2	1.308 (3)	C7—H7	0.9300
O2—C4	1.359 (3)	C8—C8ⁱ	1.352 (7)
O2—C9	1.428 (3)	C8—H8A	0.9700
O3—H3	0.847 (10)	C8—H8B	0.9700
C1—C6	1.403 (3)	C9—H9A	0.9600
C1—C2	1.424 (3)	C9—H9B	0.9600
C1—C7	1.430 (3)	C9—H9C	0.9600

O1ⁱ—Ni1—O1	91.47 (9)	O2—C4—C3	124.6 (2)
O1ⁱ—Ni1—N1ⁱ	91.48 (8)	O2—C4—C5	114.4 (2)
O1—Ni1—N1ⁱ	168.38 (9)	C3—C4—C5	121.0 (2)
O1ⁱ—Ni1—N1	168.38 (9)	C6—C5—C4	118.3 (2)
O1—Ni1—N1	91.48 (8)	C6—C5—H5	120.8
N1ⁱ—Ni1—N1	83.49 (13)	C4—C5—H5	120.8
O1ⁱ—Ni1—O3	94.00 (7)	C5—C6—C1	122.9 (2)
O1—Ni1—O3	94.00 (7)	C5—C6—H6	118.6
N1ⁱ—Ni1—O3	97.00 (8)	C1—C6—H6	118.6
N1—Ni1—O3	97.00 (8)	N1—C7—C1	125.6 (2)
C7—N1—C8	120.9 (2)	N1—C7—H7	117.2
C7—N1—Ni1	127.17 (17)	C1—C7—H7	117.2
C8—N1—Ni1	111.69 (19)	C8ⁱ—C8—N1	115.27 (16)
C2—O1—Ni1	127.95 (14)	C8ⁱ—C8—H8A	108.5
C4—O2—C9	118.01 (19)	N1—C8—H8A	108.5
Ni1—O3—H3	115 (2)	C8ⁱ—C8—H8B	108.5
C6—C1—C2	118.6 (2)	N1—C8—H8B	108.5
C6—C1—C7	118.6 (2)	H8A—C8—H8B	107.5
C2—C1—C7	122.8 (2)	O2—C9—H9A	109.5
O1—C2—C3	118.17 (19)	O2—C9—H9B	109.5
O1—C2—C1	123.9 (2)	H9A—C9—H9B	109.5
C3—C2—C1	117.9 (2)	O2—C9—H9C	109.5
C4—C3—C2	121.2 (2)	H9A—C9—H9C	109.5
C4—C3—H3A	119.4	H9B—C9—H9C	109.5
C2—C3—H3A	119.4

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱⁱ	0.85 (1)	1.97 (2)	2.734 (2)	150 (3)

Symmetry code: (ii) x+1/2, y, −z+5/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₈H₁₈N₂O₄)(H₂O)]
M_r	403.07
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	298
a, b, c (Å)	8.7698 (3), 27.0608 (9), 7.4731 (2)
V (Å³)	1773.5 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.18 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.823, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	9937, 1978, 1762
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.085, 1.04
No. of reflections	1978
No. of parameters	125
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.46

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.847 (10)	1.969 (17)	2.734 (2)	150 (3)

Symmetry code: (i) x+1/2, y, −z+5/2.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

Angulo, I. M., Bouwman, E., Lutz, M., Mul, W. P. & Spek, A. L. (2001). Inorg. Chem. 40, 2073–2082. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Dey, S. K., Mondal, N., El Fallah, M. S., Vicente, R., Escuer, A., Solans, X., Font-Bardia, M., Matsushita, T., Gramlich, V. & Mitra, S. (2004). Inorg. Chem. 43, 2427–2434. Web of Science CSD CrossRef PubMed CAS Google Scholar
Edison, S. E., Krause Bauer, J. A. & Baldwin, M. J. (2004). Acta Cryst. E60, m1930-m1932. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (1996). 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
Suh, M. P., Oh, K. Y., Lee, J. W. & Bae, Y. Y. (1996). J. Am. Chem. Soc. 118, 777–783. CSD CrossRef CAS Web of Science Google Scholar
Tang, C. (2009). Acta Cryst. E65, m317. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1278

https://doi.org/10.1107/S1600536809039129

Open

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

Aqua{5,5′-di­meth­oxy-2,2-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}nickel(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Aqua{5,5′-dimethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)