Aqua­{6,6′-dieth­oxy-2,2′-[ethane-1,2-diyl­bis(nitrilo­methanylyl­idene)]diphen­olato}zinc

Wang, C.-Y.; Wu, X.; Hu, J.-J.; Han, Z.-P.

doi:10.1107/S1600536811031497

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1220

doi:10.1107/S1600536811031497

Open

access

Aqua{6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}zinc

Chen-Yi Wang,^a ^* Xiang Wu,^a Juan-Juan Hu ^b and Zhi-Ping Han ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China, and ^bHuzhou No. 11 Middle School, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 3 August 2011; accepted 4 August 2011; online 11 August 2011)

The mononuclear zinc title complex, [Zn(C₂₀H₂₂N₂O₄)(H₂O)], was obtained by the reaction of 3-ethoxysalicylaldehyde, ethane-1,2-diamine, and zinc acetate in methanol. The Zn atom is five-coordinated by two phenolate O and two imine N atoms of the tetradentate Schiff base ligand and by one water O atom, forming a square-pyramidal geometry. In the crystal, pairs of molecules are linked via intermolecular O—H⋯O hydrogen bonds, forming dimers.

Related literature

For Schiff base complexes reported by our group, see: Wang (2009 ); Wang & Ye (2011 ). For similar zinc complexes, see: Meyer & Roesky (2007 ); Chu et al. (2008 ); Szlyk et al. (2005 ); Reglinski et al. (2002 ).

Experimental

Crystal data

[Zn(C₂₀H₂₂N₂O₄)(H₂O)]
M_r = 437.78
Monoclinic, P 2₁ /c
a = 13.545 (3) Å
b = 11.550 (2) Å
c = 14.327 (3) Å
β = 115.656 (3)°
V = 2020.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.762, T_max = 0.788
10161 measured reflections
3724 independent reflections
2607 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.085
S = 1.01
3724 reflections
261 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	1.9737 (19)
Zn1—O2	1.9990 (18)
Zn1—O5	2.040 (2)
Zn1—N2	2.075 (2)
Zn1—N1	2.080 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3ⁱ	0.85 (1)	2.41 (2)	3.128 (3)	143 (3)
O5—H5A⋯O1ⁱ	0.85 (1)	2.03 (2)	2.781 (3)	147 (3)
O5—H5B⋯O4ⁱ	0.84 (1)	2.42 (2)	3.104 (3)	139 (3)
O5—H5B⋯O2ⁱ	0.84 (1)	1.96 (2)	2.722 (2)	149 (3)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536811031497/hg5074sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031497/hg5074Isup2.hkl

checkCIF report

Comment top

As part of our investigations into Schiff base complexes (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear zinc(II) complex, Fig. 1. The Zn atom in the complex is five-coordinated by two phenolate O and two imine N atoms of the Schiff base ligand, and by one water O atom, forming a square pyramidal geometry. The Zn atom deviates from the least squares plane defined by the four basal donor atoms by 0.449 (2) Å. The Zn–O and Zn–N bond lengths (Table 1) are typical and are comparable with those observed in other similar zinc(II) complexes (Meyer & Roesky, 2007; Chu et al., 2008; Szlyk et al., 2005; Reglinski et al., 2002).

In the crystal structure, adjacent two molecules are linked via intermolecular O—H···O hydrogen bonds, to form a dimer (Table 1, Fig. 2).

Related literature top

For Schiff base complexes reported by our group, see: Wang (2009); Wang & Ye (2011). For similar zinc(II) complexes, see: Meyer & Roesky (2007); Chu et al. (2008); Szlyk et al. (2005); Reglinski et al. (2002).

Experimental top

3-Ethoxysalicylaldehyde (1.0 mmol, 0.166 g) and ethane-1,2-diamine (0.5 mmol, 0.030 g) were dissolved in MeOH (30 ml), to the mixture was added with stirring an aqueous solution (5 ml) of zinc acetate dihydrate (0.5 mmol, 0.110 g). The final mixture was stirred at room temperature for 10 min to give a clear colorless solution. After keeping the solution in air for a week, colorless block-shaped crystals were formed at the bottom of the vessel.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines. Hydrogen atoms not related to the hydrogen bonding are omitted.

Aqua{6,6'-diethoxy-2,2'-[ethane-1,2- diylbis(nitrilomethanylylidene)]diphenolato}zinc top

Crystal data top

[Zn(C₂₀H₂₂N₂O₄)(H₂O)]	F(000) = 912
M_r = 437.78	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1989 reflections
a = 13.545 (3) Å	θ = 2.3–24.9°
b = 11.550 (2) Å	µ = 1.25 mm⁻¹
c = 14.327 (3) Å	T = 298 K
β = 115.656 (3)°	Block, colorless
V = 2020.4 (7) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.762, T_max = 0.788	k = −9→13
10161 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.034P)² + 0.0614P] where P = (F_o² + 2F_c²)/3
3724 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.37 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Zn(C₂₀H₂₂N₂O₄)(H₂O)]	V = 2020.4 (7) Å³
M_r = 437.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.545 (3) Å	µ = 1.25 mm⁻¹
b = 11.550 (2) Å	T = 298 K
c = 14.327 (3) Å	0.23 × 0.20 × 0.20 mm
β = 115.656 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3724 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2607 reflections with I > 2σ(I)
T_min = 0.762, T_max = 0.788	R_int = 0.045
10161 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	3 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.37 e Å⁻³
3724 reflections	Δρ_min = −0.28 e Å⁻³
261 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	0.49151 (3)	0.37501 (3)	0.10550 (2)	0.03753 (13)
N1	0.3923 (2)	0.2318 (2)	0.08934 (18)	0.0452 (6)
N2	0.5943 (2)	0.2758 (2)	0.23068 (18)	0.0443 (6)
O1	0.35950 (15)	0.47362 (17)	0.05034 (14)	0.0437 (5)
O2	0.59290 (15)	0.50826 (15)	0.16851 (13)	0.0408 (5)
O3	0.22138 (17)	0.63806 (19)	−0.04018 (17)	0.0591 (6)
O4	0.70129 (17)	0.70006 (18)	0.19471 (16)	0.0554 (6)
O5	0.52911 (16)	0.34179 (17)	−0.01527 (15)	0.0418 (5)
C1	0.2173 (3)	0.3281 (3)	0.0021 (2)	0.0491 (8)
C2	0.2562 (2)	0.4425 (3)	0.0042 (2)	0.0401 (7)
C3	0.1772 (3)	0.5299 (3)	−0.0450 (2)	0.0507 (8)
C4	0.0662 (3)	0.5050 (4)	−0.0929 (3)	0.0706 (11)
H4	0.0157	0.5640	−0.1236	0.085*
C5	0.0303 (3)	0.3914 (4)	−0.0949 (3)	0.0858 (14)
H5	−0.0440	0.3742	−0.1287	0.103*
C6	0.1032 (3)	0.3068 (4)	−0.0480 (3)	0.0694 (11)
H6	0.0778	0.2319	−0.0485	0.083*
C7	0.2873 (3)	0.2305 (3)	0.0488 (2)	0.0492 (8)
H7	0.2537	0.1606	0.0496	0.059*
C8	0.4581 (3)	0.1297 (3)	0.1400 (2)	0.0559 (9)
H8A	0.4930	0.0987	0.0988	0.067*
H8B	0.4121	0.0699	0.1481	0.067*
C9	0.5436 (3)	0.1685 (3)	0.2447 (2)	0.0560 (9)
H9A	0.5097	0.1823	0.2911	0.067*
H9B	0.5989	0.1089	0.2748	0.067*
C10	0.6950 (3)	0.2982 (3)	0.2888 (2)	0.0508 (9)
H10	0.7354	0.2413	0.3357	0.061*
C11	0.7511 (2)	0.4034 (3)	0.2882 (2)	0.0463 (8)
C12	0.6982 (2)	0.5033 (3)	0.2313 (2)	0.0390 (7)
C13	0.7612 (2)	0.6054 (3)	0.2452 (2)	0.0477 (8)
C14	0.8727 (3)	0.6055 (3)	0.3066 (3)	0.0651 (10)
H14	0.9134	0.6722	0.3122	0.078*
C15	0.9243 (3)	0.5060 (4)	0.3601 (3)	0.0777 (12)
H15	0.9995	0.5065	0.4012	0.093*
C16	0.8658 (3)	0.4077 (4)	0.3528 (3)	0.0674 (11)
H16	0.9012	0.3425	0.3906	0.081*
C17	0.1503 (3)	0.7298 (3)	−0.0960 (3)	0.0694 (11)
H17A	0.0975	0.7450	−0.0685	0.083*
H17B	0.1107	0.7091	−0.1685	0.083*
C18	0.2193 (4)	0.8354 (3)	−0.0848 (3)	0.0903 (14)
H18A	0.2598	0.8538	−0.0128	0.135*
H18B	0.1728	0.8995	−0.1199	0.135*
H18C	0.2693	0.8205	−0.1147	0.135*
C19	0.7526 (3)	0.8113 (3)	0.2181 (3)	0.0670 (11)
H19A	0.8031	0.8193	0.1869	0.080*
H19B	0.7931	0.8209	0.2924	0.080*
C20	0.6637 (4)	0.8998 (3)	0.1749 (3)	0.0911 (14)
H20A	0.6247	0.8898	0.1013	0.137*
H20B	0.6952	0.9759	0.1897	0.137*
H20C	0.6140	0.8906	0.2060	0.137*
H5B	0.4751 (16)	0.367 (3)	−0.0680 (17)	0.080*
H5A	0.5844 (15)	0.379 (3)	−0.013 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0370 (2)	0.0343 (2)	0.0395 (2)	0.00106 (17)	0.01491 (15)	0.00468 (17)
N1	0.0494 (17)	0.0389 (15)	0.0484 (15)	0.0003 (13)	0.0222 (13)	0.0062 (13)
N2	0.0522 (17)	0.0392 (15)	0.0417 (14)	0.0046 (13)	0.0205 (13)	0.0086 (12)
O1	0.0320 (12)	0.0407 (12)	0.0528 (12)	−0.0006 (10)	0.0130 (10)	−0.0009 (10)
O2	0.0332 (11)	0.0366 (11)	0.0417 (11)	0.0014 (9)	0.0061 (9)	0.0019 (10)
O3	0.0442 (13)	0.0526 (15)	0.0689 (15)	0.0142 (12)	0.0137 (11)	0.0076 (13)
O4	0.0525 (14)	0.0398 (13)	0.0657 (14)	−0.0078 (12)	0.0180 (12)	−0.0060 (12)
O5	0.0433 (12)	0.0382 (12)	0.0430 (12)	0.0033 (10)	0.0177 (10)	0.0028 (10)
C1	0.043 (2)	0.057 (2)	0.0493 (19)	−0.0085 (18)	0.0224 (16)	−0.0040 (17)
C2	0.0330 (17)	0.052 (2)	0.0360 (16)	−0.0010 (16)	0.0156 (14)	−0.0049 (15)
C3	0.0376 (19)	0.061 (2)	0.0492 (18)	0.0028 (18)	0.0148 (15)	−0.0022 (18)
C4	0.037 (2)	0.087 (3)	0.076 (2)	0.011 (2)	0.0127 (18)	0.003 (2)
C5	0.037 (2)	0.104 (4)	0.099 (3)	−0.014 (3)	0.013 (2)	−0.008 (3)
C6	0.044 (2)	0.080 (3)	0.080 (3)	−0.015 (2)	0.024 (2)	−0.005 (2)
C7	0.054 (2)	0.044 (2)	0.0536 (19)	−0.0126 (18)	0.0268 (17)	−0.0030 (17)
C8	0.072 (2)	0.0368 (19)	0.067 (2)	−0.0026 (19)	0.038 (2)	0.0096 (18)
C9	0.076 (2)	0.0406 (19)	0.052 (2)	0.0062 (19)	0.0281 (19)	0.0165 (17)
C10	0.055 (2)	0.052 (2)	0.0407 (18)	0.0193 (18)	0.0168 (17)	0.0111 (16)
C11	0.0351 (17)	0.058 (2)	0.0403 (17)	0.0097 (16)	0.0109 (14)	0.0052 (16)
C12	0.0360 (18)	0.0469 (19)	0.0335 (15)	0.0027 (15)	0.0144 (14)	−0.0043 (14)
C13	0.0387 (18)	0.058 (2)	0.0406 (17)	−0.0026 (17)	0.0121 (15)	−0.0064 (16)
C14	0.043 (2)	0.085 (3)	0.059 (2)	−0.015 (2)	0.0145 (18)	−0.003 (2)
C15	0.030 (2)	0.115 (4)	0.068 (2)	0.003 (2)	0.0026 (18)	0.013 (3)
C16	0.039 (2)	0.085 (3)	0.064 (2)	0.011 (2)	0.0084 (18)	0.021 (2)
C17	0.067 (2)	0.075 (3)	0.064 (2)	0.033 (2)	0.027 (2)	0.018 (2)
C18	0.102 (3)	0.063 (3)	0.121 (4)	0.026 (3)	0.063 (3)	0.035 (3)
C19	0.082 (3)	0.053 (2)	0.072 (2)	−0.027 (2)	0.039 (2)	−0.014 (2)
C20	0.127 (4)	0.043 (2)	0.118 (3)	−0.006 (3)	0.067 (3)	−0.006 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.9737 (19)	C8—C9	1.513 (4)
Zn1—O2	1.9990 (18)	C8—H8A	0.9700
Zn1—O5	2.040 (2)	C8—H8B	0.9700
Zn1—N2	2.075 (2)	C9—H9A	0.9700
Zn1—N1	2.080 (2)	C9—H9B	0.9700
N1—C7	1.282 (4)	C10—C11	1.435 (4)
N1—C8	1.467 (4)	C10—H10	0.9300
N2—C10	1.279 (4)	C11—C12	1.416 (4)
N2—C9	1.473 (4)	C11—C16	1.424 (4)
O1—C2	1.312 (3)	C12—C13	1.418 (4)
O2—C12	1.317 (3)	C13—C14	1.381 (4)
O3—C3	1.374 (4)	C14—C15	1.391 (5)
O3—C17	1.423 (4)	C14—H14	0.9300
O4—C13	1.367 (3)	C15—C16	1.362 (5)
O4—C19	1.429 (3)	C15—H15	0.9300
O5—H5B	0.843 (10)	C16—H16	0.9300
O5—H5A	0.850 (10)	C17—C18	1.502 (5)
C1—C6	1.417 (4)	C17—H17A	0.9700
C1—C2	1.418 (4)	C17—H17B	0.9700
C1—C7	1.438 (4)	C18—H18A	0.9600
C2—C3	1.417 (4)	C18—H18B	0.9600
C3—C4	1.386 (4)	C18—H18C	0.9600
C4—C5	1.396 (5)	C19—C20	1.494 (5)
C4—H4	0.9300	C19—H19A	0.9700
C5—C6	1.343 (5)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600

O1—Zn1—O2	93.60 (8)	N2—C9—H9A	110.0
O1—Zn1—O5	106.53 (8)	C8—C9—H9A	110.0
O2—Zn1—O5	98.79 (8)	N2—C9—H9B	110.0
O1—Zn1—N2	144.82 (9)	C8—C9—H9B	110.0
O2—Zn1—N2	87.82 (9)	H9A—C9—H9B	108.4
O5—Zn1—N2	107.97 (9)	N2—C10—C11	125.8 (3)
O1—Zn1—N1	89.13 (9)	N2—C10—H10	117.1
O2—Zn1—N1	161.26 (8)	C11—C10—H10	117.1
O5—Zn1—N1	98.18 (9)	C12—C11—C16	118.9 (3)
N2—Zn1—N1	79.43 (10)	C12—C11—C10	123.8 (3)
C7—N1—C8	122.1 (3)	C16—C11—C10	117.2 (3)
C7—N1—Zn1	126.6 (2)	O2—C12—C11	123.9 (3)
C8—N1—Zn1	111.09 (19)	O2—C12—C13	117.9 (3)
C10—N2—C9	120.7 (3)	C11—C12—C13	118.2 (3)
C10—N2—Zn1	125.3 (2)	O4—C13—C14	124.8 (3)
C9—N2—Zn1	113.86 (19)	O4—C13—C12	114.1 (3)
C2—O1—Zn1	128.84 (19)	C14—C13—C12	121.1 (3)
C12—O2—Zn1	127.15 (18)	C13—C14—C15	120.0 (3)
C3—O3—C17	118.4 (3)	C13—C14—H14	120.0
C13—O4—C19	118.5 (2)	C15—C14—H14	120.0
Zn1—O5—H5B	105 (2)	C16—C15—C14	120.7 (3)
Zn1—O5—H5A	114 (2)	C16—C15—H15	119.7
H5B—O5—H5A	106 (2)	C14—C15—H15	119.7
C6—C1—C2	119.1 (3)	C15—C16—C11	120.9 (3)
C6—C1—C7	117.1 (3)	C15—C16—H16	119.5
C2—C1—C7	123.8 (3)	C11—C16—H16	119.5
O1—C2—C3	117.8 (3)	O3—C17—C18	107.8 (3)
O1—C2—C1	124.8 (3)	O3—C17—H17A	110.1
C3—C2—C1	117.4 (3)	C18—C17—H17A	110.1
O3—C3—C4	124.7 (3)	O3—C17—H17B	110.1
O3—C3—C2	113.8 (3)	C18—C17—H17B	110.1
C4—C3—C2	121.5 (3)	H17A—C17—H17B	108.4
C3—C4—C5	120.0 (4)	C17—C18—H18A	109.5
C3—C4—H4	120.0	C17—C18—H18B	109.5
C5—C4—H4	120.0	H18A—C18—H18B	109.5
C6—C5—C4	119.9 (3)	C17—C18—H18C	109.5
C6—C5—H5	120.0	H18A—C18—H18C	109.5
C4—C5—H5	120.0	H18B—C18—H18C	109.5
C5—C6—C1	122.1 (4)	O4—C19—C20	107.1 (3)
C5—C6—H6	118.9	O4—C19—H19A	110.3
C1—C6—H6	118.9	C20—C19—H19A	110.3
N1—C7—C1	125.5 (3)	O4—C19—H19B	110.3
N1—C7—H7	117.3	C20—C19—H19B	110.3
C1—C7—H7	117.3	H19A—C19—H19B	108.5
N1—C8—C9	107.0 (2)	C19—C20—H20A	109.5
N1—C8—H8A	110.3	C19—C20—H20B	109.5
C9—C8—H8A	110.3	H20A—C20—H20B	109.5
N1—C8—H8B	110.3	C19—C20—H20C	109.5
C9—C8—H8B	110.3	H20A—C20—H20C	109.5
H8A—C8—H8B	108.6	H20B—C20—H20C	109.5
N2—C9—C8	108.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱ	0.85 (1)	2.41 (2)	3.128 (3)	143 (3)
O5—H5A···O1ⁱ	0.85 (1)	2.03 (2)	2.781 (3)	147 (3)
O5—H5B···O4ⁱ	0.84 (1)	2.42 (2)	3.104 (3)	139 (3)
O5—H5B···O2ⁱ	0.84 (1)	1.96 (2)	2.722 (2)	149 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Zn(C₂₀H₂₂N₂O₄)(H₂O)]
M_r	437.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.545 (3), 11.550 (2), 14.327 (3)
β (°)	115.656 (3)
V (Å³)	2020.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.762, 0.788
No. of measured, independent and observed [I > 2σ(I)] reflections	10161, 3724, 2607
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.085, 1.01
No. of reflections	3724
No. of parameters	261
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	1.9737 (19)	Zn1—N2	2.075 (2)
Zn1—O2	1.9990 (18)	Zn1—N1	2.080 (2)
Zn1—O5	2.040 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱ	0.850 (10)	2.41 (2)	3.128 (3)	143 (3)
O5—H5A···O1ⁱ	0.850 (10)	2.03 (2)	2.781 (3)	147 (3)
O5—H5B···O4ⁱ	0.843 (10)	2.42 (2)	3.104 (3)	139 (3)
O5—H5B···O2ⁱ	0.843 (10)	1.964 (19)	2.722 (2)	149 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Natural Science Foundation of Zhejiang Province (No. Y407318) and the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chu, Z., Huang, W., Wang, L. & Gou, S. (2008). Polyhedron, 27, 1079–1092. Web of Science CSD CrossRef CAS Google Scholar
Meyer, N. & Roesky, P. W. (2007). Z. Anorg. Allg. Chem. 633, 2292–2295. CrossRef CAS Google Scholar
Reglinski, J., Morris, S. & Stevenson, D. E. (2002). Polyhedron, 21, 2175–2182. Web of Science CSD CrossRef CAS Google Scholar
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
Szlyk, E., Wojtczak, A., Surdykowski, A. & Gozdzikiewicz, M. (2005). Inorg. Chim. Acta, 358, 467–475. CAS Google Scholar
Wang, C.-Y. (2009). J. Coord. Chem. 62, 2860–2868. Web of Science CSD CrossRef CAS Google Scholar
Wang, C. Y. & Ye, J. Y. (2011). Russ. J. Coord. Chem. 37, 235–241. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1220

doi:10.1107/S1600536811031497

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Aqua­{6,6′-dieth­­oxy-2,2′-[ethane-1,2-diyl­bis­(nitrilo­methanylyl­­idene)]diphen­olato}zinc

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Aqua{6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}zinc