{6,6′-Dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}zinc(II) monohydrate

Shen, Y.-M.; Wang, W.

doi:10.1107/S1600536809010344

metal-organic compounds

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Volume 65| Part 4| April 2009| Page m444

doi:10.1107/S1600536809010344

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{6,6′-Diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}zinc(II) monohydrate

Yong-Miao Shen ^a and Wei Wang ^b ^*

^aDepartment of Chemistry, Shaoxing University, Shaoxing 312000, People's Republic of China, and ^bYancheng Institute of Technology, School of Chemical and Biological Engineering, Yancheng 224003, People's Republic of China
^*Correspondence e-mail: chemreagent@yahoo.cn

(Received 28 February 2009; accepted 20 March 2009; online 25 March 2009)

The molecule of the title compound, [Zn(C₂₀H₂₂N₂O₄)]·H₂O, deviates from planarity with a dihedral angle between the two benzene rings is 18.3 (1)°. The four-coordinate Zn^II ion has a distorted square-planar coordination and is N₂O₂-chelated by the Schiff base ligand. The Zn^II ion and solvent water molecule are located on a twofold rotation axis. The structure displays intermolecular O—H⋯O hydrogen bonding.

Related literature

For the chemical properties of Schiff bases, see: Lindoy et al. (1976 ). For N,N′-disalicylideneethylenediamine complexes, see: Correia et al. (2005 ); Cunningham et al. (2000 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Zn(C₂₀H₂₂N₂O₄)]·H₂O
M_r = 437.78
Orthorhombic, P b c n
a = 12.6512 (16) Å
b = 19.986 (3) Å
c = 7.8708 (10) Å
V = 1990.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 273 K
0.25 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.742, T_max = 0.813
9492 measured reflections
1855 independent reflections
1423 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.101
S = 1.04
1855 reflections
133 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 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—H3A⋯O1ⁱ	0.807 (10)	2.91 (5)	3.071 (4)	94 (3)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

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 in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010344/pk2159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010344/pk2159Isup2.hkl

checkCIF report

Comment top

The schiff bases have been extensively studied as effective ligands for metal ions and used in the mechanism of many biochemical processes (Lindoy et al., 1976). N,N-disalicylideneethylenediamine type schiff bases ligands present versatile steric, electronic and lipophilic properties (Correia et al. 2005; Cunningham et al. 2000). We report here the synthesis and crystal structure of the title compound. The molecular structure is shown in Fig.1. The values of the geometric parameters in the structure are normal (Allen et al., 1987). The interplanar angles beween the the two phenyl group is 18.3 (1)°. The four-coordinate Zn gives plane coordination.

Related literature top

For the chemical properties of Schiff bases, see: Lindoy et al. (1976). For the N,N'-disalicylideneethylenediamine complexes, see: Correia et al. (2005); Cunningham et al. (2000). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 6,6'-Diethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol (0.1 mmol) and zinc acetate (0.1 mmol) in absolute methanol (20 ml) was heated at 50 centidegree and stirred for 30 min, then filtered. The resulting clear orange solution was moved to a tube, some ethyl ether was added, and then after 14 days, block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained(yield: about 40%).

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 in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

{6,6'-Diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}zinc(II) monohydrate top

Crystal data top

[Zn(C₂₀H₂₂N₂O₄)]·H₂O	F(000) = 912
M_r = 437.78	D_x = 1.461 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2488 reflections
a = 12.6512 (16) Å	θ = 3.3–24.0°
b = 19.986 (3) Å	µ = 1.27 mm⁻¹
c = 7.8708 (10) Å	T = 273 K
V = 1990.1 (4) Å³	Needle, colourless
Z = 4	0.25 × 0.21 × 0.17 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1855 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→13
T_min = 0.742, T_max = 0.813	k = −24→23
9492 measured reflections	l = −9→9

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) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0592P)² + 0.4077P] where P = (F_o² + 2F_c²)/3
1855 reflections	(Δ/σ)_max = 0.034
133 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Zn(C₂₀H₂₂N₂O₄)]·H₂O	V = 1990.1 (4) Å³
M_r = 437.78	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.6512 (16) Å	µ = 1.27 mm⁻¹
b = 19.986 (3) Å	T = 273 K
c = 7.8708 (10) Å	0.25 × 0.21 × 0.17 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1855 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1423 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.813	R_int = 0.031
9492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
1855 reflections	Δρ_min = −0.46 e Å⁻³
133 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
Zn1	0.5000	0.475277 (19)	0.2500	0.04314 (18)
O1	0.40642 (12)	0.40659 (8)	0.1698 (2)	0.0441 (4)
O2	0.31927 (13)	0.29902 (8)	0.0342 (2)	0.0491 (4)
O3	0.5000	0.26838 (19)	0.2500	0.0940 (13)
N1	0.40920 (19)	0.54832 (10)	0.1725 (3)	0.0519 (6)
C1	0.2641 (2)	0.47896 (14)	0.0770 (3)	0.0530 (7)
C2	0.31464 (18)	0.41541 (12)	0.0957 (3)	0.0422 (6)
C3	0.26222 (19)	0.35776 (13)	0.0260 (3)	0.0468 (6)
C4	0.1632 (2)	0.36235 (17)	−0.0434 (4)	0.0619 (8)
H4	0.1294	0.3244	−0.0849	0.074*
C5	0.1133 (2)	0.4253 (2)	−0.0514 (4)	0.0800 (10)
H5	0.0453	0.4284	−0.0957	0.096*
C6	0.1628 (3)	0.48188 (19)	0.0045 (4)	0.0740 (10)
H6	0.1289	0.5230	−0.0055	0.089*
C7	0.3159 (2)	0.54153 (14)	0.1154 (4)	0.0588 (8)
H7	0.2774	0.5805	0.0967	0.071*
C8	0.2840 (2)	0.24216 (14)	−0.0638 (4)	0.0590 (8)
H8A	0.2683	0.2559	−0.1792	0.071*
H8B	0.2201	0.2238	−0.0142	0.071*
C9	0.3688 (3)	0.19045 (15)	−0.0647 (4)	0.0726 (9)
H9A	0.4320	0.2090	−0.1130	0.109*
H9B	0.3463	0.1528	−0.1312	0.109*
H9C	0.3827	0.1762	0.0496	0.109*
C10	0.4568 (3)	0.61556 (13)	0.1843 (4)	0.0651 (8)
H10A	0.4030	0.6479	0.2152	0.078*
H10B	0.4857	0.6283	0.0748	0.078*
H3A	0.487 (4)	0.2934 (18)	0.172 (4)	0.126 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0450 (3)	0.0357 (3)	0.0487 (3)	0.000	0.00991 (18)	0.000
O1	0.0357 (9)	0.0407 (9)	0.0558 (11)	0.0034 (7)	−0.0043 (8)	0.0012 (8)
O2	0.0455 (10)	0.0505 (10)	0.0513 (10)	−0.0085 (8)	−0.0114 (8)	0.0028 (8)
O3	0.096 (3)	0.054 (2)	0.132 (4)	0.000	−0.064 (3)	0.000
N1	0.0604 (15)	0.0394 (11)	0.0558 (14)	0.0128 (11)	0.0222 (12)	0.0062 (11)
C1	0.0456 (15)	0.0639 (18)	0.0496 (16)	0.0188 (12)	0.0072 (13)	0.0064 (13)
C2	0.0342 (12)	0.0563 (15)	0.0361 (13)	0.0052 (11)	0.0062 (10)	0.0073 (11)
C3	0.0378 (14)	0.0650 (17)	0.0376 (13)	0.0001 (12)	0.0031 (10)	0.0109 (12)
C4	0.0378 (15)	0.095 (2)	0.0526 (17)	−0.0027 (15)	−0.0049 (12)	0.0055 (16)
C5	0.0401 (17)	0.126 (3)	0.074 (2)	0.0183 (19)	−0.0085 (15)	0.012 (2)
C6	0.054 (2)	0.091 (2)	0.077 (2)	0.0321 (17)	−0.0010 (15)	0.011 (2)
C7	0.0645 (19)	0.0545 (17)	0.0575 (17)	0.0282 (15)	0.0164 (15)	0.0095 (14)
C8	0.0666 (18)	0.0623 (18)	0.0481 (15)	−0.0252 (15)	−0.0096 (14)	0.0051 (13)
C9	0.092 (2)	0.0575 (18)	0.068 (2)	−0.0142 (17)	−0.0122 (18)	−0.0091 (15)
C10	0.090 (2)	0.0338 (14)	0.071 (2)	0.0088 (13)	0.0375 (16)	0.0048 (13)

Geometric parameters (Å, º) top

Zn1—O1	1.9195 (16)	C4—C5	1.410 (5)
Zn1—O1ⁱ	1.9195 (16)	C4—H4	0.9300
Zn1—N1ⁱ	1.955 (2)	C5—C6	1.365 (5)
Zn1—N1	1.955 (2)	C5—H5	0.9300
O1—C2	1.311 (3)	C6—H6	0.9300
O2—C3	1.380 (3)	C7—H7	0.9300
O2—C8	1.444 (3)	C8—C9	1.489 (4)
O3—H3A	0.807 (10)	C8—H8A	0.9700
N1—C7	1.270 (4)	C8—H8B	0.9700
N1—C10	1.476 (3)	C9—H9A	0.9600
C1—C6	1.404 (4)	C9—H9B	0.9600
C1—C2	1.429 (3)	C9—H9C	0.9600
C1—C7	1.444 (4)	C10—C10ⁱ	1.505 (7)
C2—C3	1.438 (3)	C10—H10A	0.9700
C3—C4	1.369 (4)	C10—H10B	0.9700

O1—Zn1—O1ⁱ	88.69 (9)	C4—C5—H5	119.4
O1—Zn1—N1ⁱ	177.35 (8)	C5—C6—C1	121.0 (3)
O1ⁱ—Zn1—N1ⁱ	93.95 (9)	C5—C6—H6	119.5
O1—Zn1—N1	93.95 (9)	C1—C6—H6	119.5
O1ⁱ—Zn1—N1	177.35 (8)	N1—C7—C1	126.1 (2)
N1ⁱ—Zn1—N1	83.40 (15)	N1—C7—H7	117.0
C2—O1—Zn1	126.60 (15)	C1—C7—H7	117.0
C3—O2—C8	118.9 (2)	O2—C8—C9	109.0 (2)
C7—N1—C10	119.9 (2)	O2—C8—H8A	109.9
C7—N1—Zn1	125.21 (19)	C9—C8—H8A	109.9
C10—N1—Zn1	114.9 (2)	O2—C8—H8B	109.9
C6—C1—C2	119.1 (3)	C9—C8—H8B	109.9
C6—C1—C7	117.6 (3)	H8A—C8—H8B	108.3
C2—C1—C7	123.0 (3)	C8—C9—H9A	109.5
O1—C2—C1	124.1 (2)	C8—C9—H9B	109.5
O1—C2—C3	118.0 (2)	H9A—C9—H9B	109.5
C1—C2—C3	117.8 (2)	C8—C9—H9C	109.5
C4—C3—O2	123.6 (3)	H9A—C9—H9C	109.5
C4—C3—C2	121.3 (2)	H9B—C9—H9C	109.5
O2—C3—C2	115.0 (2)	N1—C10—C10ⁱ	109.85 (18)
C3—C4—C5	119.2 (3)	N1—C10—H10A	109.7
C3—C4—H4	120.4	C10ⁱ—C10—H10A	109.7
C5—C4—H4	120.4	N1—C10—H10B	109.7
C6—C5—C4	121.3 (3)	C10ⁱ—C10—H10B	109.7
C6—C5—H5	119.4	H10A—C10—H10B	108.2

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···O1ⁱ	0.81 (1)	2.91 (5)	3.071 (4)	94 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₂₀H₂₂N₂O₄)]·H₂O
M_r	437.78
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	273
a, b, c (Å)	12.6512 (16), 19.986 (3), 7.8708 (10)
V (Å³)	1990.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.25 × 0.21 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.742, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	9492, 1855, 1423
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.101, 1.04
No. of reflections	1855
No. of parameters	133
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)	0.24, −0.46

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.807 (10)	2.91 (5)	3.071 (4)	94 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation (Y4080395).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Correia, I., Pessoa, J. C., Duarte, M. T., da Piedade, M. F. M., Jackush, T., Kiss, T., Castro, M. M. C. A., Geraldes, C. F. G. C. & Avecilla F. (2005). Eur. J. Inorg. Chem. pp. 732–744. Web of Science CSD CrossRef Google Scholar
Cunningham, D., McArdle, P., Mitchell, M., Chonchubhair, N. N., Gara, M. O., Franceschi, F. & Floriani, C. (2000). Inorg. Chem. 39, 1639–1649. Web of Science CrossRef PubMed CAS Google Scholar
Lindoy, L. F., Lip, H. C., Power, L. F. & Rea, T. H. (1976). Inorg. Chem. 15, 1724–1727. CrossRef CAS Web of Science 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

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m444

doi:10.1107/S1600536809010344

Open

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

{6,6′-Dieth­­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}zinc(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{6,6′-Diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}zinc(II) monohydrate