Aqua-{6,6'-dieth-oxy-2,2'-[ethane-1,2-diyl-bis(nitrilo-methanylyl-idene)]diphen-olato}zinc.

The mononuclear zinc title complex, [Zn(C(20)H(22)N(2)O(4))(H(2)O)], was obtained by the reaction of 3-eth-oxy-salicyl-aldehyde, 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 mol-ecules are linked via inter-molecular 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 = 437.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.085

S = 1.01

3724 reflections

261 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031497/hg5074sup1.cif

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

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

[Zn(C20H22N2O4)(H2O)]	F(000) = 912
Mr = 437.78	Dx = 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

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

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(Fo2) + (0.034P)2 + 0.0614P] where P = (Fo2 + 2Fc2)/3
3724 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.37 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

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
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*

	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)

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)

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)

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) .