Bis{2-hydroxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene]propanohydrazidato}zinc(II) dihydrate.

The title compound, [Zn(C(10)H(11)N(4)O(2))(2)]·2H(2)O, was prepared by the reaction between Zn(CH(3)COO)(2)·2H(2)O and 2-hydroxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene]propano-hydrazide (Hpop). The central Zn(II) atom has a distorted tetra-gonal-bipyramidal coordination geometry formed by two amide O atoms and four N atoms of two azomethine and two pyridine groups. In the crystal, complex mol-ecules form layers parallel to the crystallographic b direction. The layers are connected by O-H⋯N and O-H⋯O hydrogen bonds involving the solvent water mol-ecules.

Related literature

For zinc(II)-containing complexes with similiar ligands, see: Petrusenko et al. (1997 ▶); Comba et al. (2002 ▶); Kasuga et al. (2003 ▶). For the structural parameters of amide derivatives of 2-hydroxy­imino­propanoic acid, see: Onindo et al. (1995 ▶); Sliva et al. (1997a ▶,b ▶); Mokhir et al. (2002 ▶); Moroz et al. (2009a ▶,b ▶). For the preparation and characterization of 3d-metal complexes with 2-hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propanohydrazone, see: Moroz et al. (2008a ▶,b ▶).

Experimental

Crystal data

[Zn(C10H11N4O2)2]·2H2O

M = 539.86

Triclinic,

a = 8.3241 (3) Å

b = 10.6299 (4) Å

c = 13.9006 (5) Å

α = 94.184 (2)°

β = 101.389 (2)°

γ = 108.052 (2)°

V = 1134.48 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 100 K

0.28 × 0.07 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.743, T max = 0.977

21551 measured reflections

5171 independent reflections

4253 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.05

5171 reflections

320 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Bruker, 2004 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003351/jh2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003351/jh2129Isup2.hkl

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

[Zn(C10H11N4O2)2]·2H2O	Z = 2
Mr = 539.86	F(000) = 560
Triclinic, P1	Dx = 1.580 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3241 (3) Å	Cell parameters from 4952 reflections
b = 10.6299 (4) Å	θ = 1.0–27.5°
c = 13.9006 (5) Å	µ = 1.14 mm−1
α = 94.184 (2)°	T = 100 K
β = 101.389 (2)°	Needle, yellow
γ = 108.052 (2)°	0.28 × 0.07 × 0.02 mm
V = 1134.48 (7) Å3

Nonius KappaCCD diffractometer	5171 independent reflections
Radiation source: fine-focus sealed tube	4253 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.048
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ scans and ω scans with κ offset	h = −10→10
Absorption correction: multi-scan (SADABS; Version 2008/1; Sheldrick, 2008)	k = −13→13
Tmin = 0.743, Tmax = 0.977	l = −18→18
21551 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.8841P] where P = (Fo2 + 2Fc2)/3
5171 reflections	(Δ/σ)max < 0.001
320 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.39746 (3)	0.27581 (3)	0.304853 (19)	0.01820 (9)
O1	0.16169 (19)	0.20226 (15)	0.34643 (12)	0.0202 (3)
O2	−0.32670 (19)	−0.16202 (17)	0.32111 (13)	0.0239 (4)
H2O	−0.3576	−0.2526	0.3012	0.036*
O3	0.30726 (19)	0.37780 (16)	0.18911 (12)	0.0204 (3)
O4	0.4981 (2)	0.70910 (18)	0.00903 (13)	0.0290 (4)
H4O	0.6065	0.7601	0.0013	0.044*
O5	0.1803 (2)	0.1858 (2)	0.01793 (14)	0.0367 (4)
H5P	0.2119	0.2596	0.0646	0.055*
H5O	0.1264	0.1984	−0.0383	0.055*
O6	0.0879 (2)	0.29498 (19)	−0.16109 (14)	0.0351 (4)
H6O	0.0697	0.2177	−0.2017	0.053*
H6P	0.2077	0.3384	−0.1471	0.053*
N1	0.5988 (2)	0.2424 (2)	0.22445 (14)	0.0207 (4)
N2	0.3039 (2)	0.07661 (19)	0.24489 (14)	0.0175 (4)
N3	0.1450 (2)	0.00054 (19)	0.25994 (14)	0.0181 (4)
N4	−0.1642 (2)	−0.11100 (19)	0.29900 (15)	0.0205 (4)
N5	0.5549 (2)	0.2876 (2)	0.45404 (14)	0.0212 (4)
N6	0.5524 (2)	0.4762 (2)	0.34417 (14)	0.0190 (4)
N7	0.5460 (2)	0.55914 (19)	0.27198 (14)	0.0188 (4)
N8	0.5314 (3)	0.6441 (2)	0.09127 (15)	0.0230 (4)
C1	0.7541 (3)	0.3275 (3)	0.22043 (18)	0.0258 (5)
H1	0.7857	0.4185	0.2482	0.031*
C2	0.8707 (3)	0.2868 (3)	0.17679 (19)	0.0306 (6)
H2	0.9811	0.3486	0.1767	0.037*
C3	0.8235 (3)	0.1560 (3)	0.13393 (18)	0.0288 (6)
H3	0.9005	0.1263	0.1035	0.035*
C4	0.6620 (3)	0.0680 (3)	0.13569 (18)	0.0255 (5)
H4	0.6257	−0.0224	0.1055	0.031*
C5	0.5538 (3)	0.1148 (2)	0.18269 (16)	0.0203 (5)
C6	0.3825 (3)	0.0232 (2)	0.19170 (16)	0.0190 (5)
C7	0.3161 (3)	−0.1184 (3)	0.14258 (19)	0.0264 (5)
H7A	0.3898	−0.1670	0.1744	0.040*
H7B	0.3181	−0.1209	0.0722	0.040*
H7C	0.1966	−0.1606	0.1488	0.040*
C8	0.0873 (3)	0.0788 (2)	0.31405 (16)	0.0165 (4)
C9	−0.0868 (3)	0.0123 (2)	0.33642 (16)	0.0174 (4)
C10	−0.1580 (3)	0.0927 (2)	0.39855 (18)	0.0223 (5)
H10A	−0.2852	0.0583	0.3795	0.034*
H10B	−0.1168	0.1865	0.3883	0.034*
H10C	−0.1187	0.0860	0.4686	0.034*
C11	0.5453 (3)	0.1915 (3)	0.51063 (18)	0.0249 (5)
H11	0.4600	0.1061	0.4865	0.030*
C12	0.6559 (3)	0.2109 (3)	0.60431 (19)	0.0302 (6)
H12	0.6500	0.1389	0.6417	0.036*
C13	0.7726 (3)	0.3356 (3)	0.64108 (19)	0.0305 (6)
H13	0.8473	0.3514	0.7051	0.037*
C14	0.7817 (3)	0.4389 (3)	0.58458 (18)	0.0270 (5)
H14	0.8602	0.5265	0.6099	0.032*
C15	0.6724 (3)	0.4112 (2)	0.48927 (17)	0.0212 (5)
C16	0.6797 (3)	0.5119 (2)	0.42118 (16)	0.0194 (5)
C17	0.8289 (3)	0.6397 (2)	0.44150 (18)	0.0255 (5)
H17A	0.8476	0.6708	0.3786	0.038*
H17B	0.9338	0.6250	0.4774	0.038*
H17C	0.8032	0.7074	0.4818	0.038*
C18	0.4150 (3)	0.4947 (2)	0.19584 (17)	0.0183 (4)
C19	0.3910 (3)	0.5686 (2)	0.10840 (17)	0.0199 (5)
C20	0.2114 (3)	0.5440 (3)	0.04913 (19)	0.0290 (6)
H20A	0.2124	0.6132	0.0061	0.043*
H20B	0.1349	0.5468	0.0940	0.043*
H20C	0.1688	0.4560	0.0083	0.043*

	U11	U22	U33	U12	U13	U23
Zn1	0.01308 (13)	0.01868 (15)	0.01989 (15)	0.00111 (10)	0.00272 (10)	0.00585 (10)
O1	0.0168 (8)	0.0165 (8)	0.0252 (9)	0.0013 (6)	0.0066 (6)	0.0030 (7)
O2	0.0147 (8)	0.0208 (9)	0.0335 (10)	−0.0003 (7)	0.0097 (7)	0.0043 (7)
O3	0.0172 (8)	0.0173 (8)	0.0217 (8)	0.0009 (6)	0.0003 (6)	0.0054 (7)
O4	0.0324 (9)	0.0346 (10)	0.0252 (9)	0.0134 (8)	0.0100 (7)	0.0171 (8)
O5	0.0357 (10)	0.0396 (12)	0.0305 (10)	0.0057 (9)	0.0089 (8)	0.0057 (9)
O6	0.0248 (9)	0.0351 (11)	0.0401 (11)	0.0065 (8)	0.0062 (8)	−0.0079 (9)
N1	0.0138 (9)	0.0276 (11)	0.0197 (10)	0.0043 (8)	0.0034 (7)	0.0100 (8)
N2	0.0132 (8)	0.0207 (10)	0.0195 (10)	0.0047 (7)	0.0051 (7)	0.0083 (8)
N3	0.0134 (9)	0.0175 (10)	0.0224 (10)	0.0016 (7)	0.0067 (7)	0.0050 (8)
N4	0.0154 (9)	0.0199 (10)	0.0255 (10)	0.0022 (8)	0.0084 (8)	0.0050 (8)
N5	0.0182 (9)	0.0266 (11)	0.0214 (10)	0.0080 (8)	0.0076 (8)	0.0088 (8)
N6	0.0158 (9)	0.0230 (10)	0.0161 (9)	0.0039 (8)	0.0025 (7)	0.0038 (8)
N7	0.0169 (9)	0.0198 (10)	0.0183 (9)	0.0038 (8)	0.0035 (7)	0.0065 (8)
N8	0.0282 (11)	0.0239 (11)	0.0213 (10)	0.0116 (9)	0.0080 (8)	0.0113 (8)
C1	0.0178 (11)	0.0333 (14)	0.0240 (12)	0.0037 (10)	0.0042 (9)	0.0119 (11)
C2	0.0159 (11)	0.0499 (18)	0.0265 (13)	0.0069 (11)	0.0083 (10)	0.0175 (12)
C3	0.0204 (12)	0.0486 (17)	0.0238 (13)	0.0153 (12)	0.0098 (10)	0.0134 (12)
C4	0.0224 (12)	0.0377 (15)	0.0207 (12)	0.0136 (11)	0.0072 (10)	0.0092 (11)
C5	0.0171 (11)	0.0318 (14)	0.0146 (11)	0.0095 (10)	0.0044 (9)	0.0112 (10)
C6	0.0156 (10)	0.0267 (13)	0.0153 (11)	0.0068 (9)	0.0037 (8)	0.0071 (9)
C7	0.0252 (12)	0.0289 (14)	0.0269 (13)	0.0087 (10)	0.0110 (10)	0.0032 (11)
C8	0.0141 (10)	0.0185 (11)	0.0163 (11)	0.0044 (9)	0.0023 (8)	0.0070 (9)
C9	0.0132 (10)	0.0196 (12)	0.0189 (11)	0.0039 (9)	0.0040 (8)	0.0060 (9)
C10	0.0161 (11)	0.0220 (12)	0.0270 (12)	0.0026 (9)	0.0072 (9)	0.0019 (10)
C11	0.0239 (12)	0.0290 (14)	0.0259 (13)	0.0099 (10)	0.0104 (10)	0.0115 (10)
C12	0.0324 (14)	0.0428 (16)	0.0264 (13)	0.0204 (12)	0.0137 (11)	0.0198 (12)
C13	0.0254 (13)	0.0471 (17)	0.0229 (13)	0.0151 (12)	0.0068 (10)	0.0128 (12)
C14	0.0197 (11)	0.0385 (15)	0.0204 (12)	0.0073 (10)	0.0022 (9)	0.0057 (11)
C15	0.0149 (10)	0.0300 (13)	0.0189 (11)	0.0074 (9)	0.0052 (9)	0.0035 (10)
C16	0.0154 (10)	0.0240 (12)	0.0164 (11)	0.0041 (9)	0.0028 (8)	0.0015 (9)
C17	0.0200 (11)	0.0252 (13)	0.0238 (12)	0.0005 (10)	−0.0001 (9)	0.0016 (10)
C18	0.0136 (10)	0.0202 (12)	0.0218 (11)	0.0053 (9)	0.0054 (9)	0.0054 (9)
C19	0.0207 (11)	0.0176 (11)	0.0205 (11)	0.0058 (9)	0.0034 (9)	0.0029 (9)
C20	0.0241 (12)	0.0321 (15)	0.0277 (13)	0.0083 (11)	−0.0011 (10)	0.0096 (11)

Zn1—N2	2.061 (2)	C3—C4	1.385 (3)
Zn1—N6	2.085 (2)	C3—H3	0.9500
Zn1—O1	2.0880 (15)	C4—C5	1.396 (3)
Zn1—O3	2.1470 (15)	C4—H4	0.9500
Zn1—N5	2.1955 (19)	C5—C6	1.492 (3)
Zn1—N1	2.2877 (19)	C6—C7	1.491 (3)
O1—C8	1.268 (3)	C7—H7A	0.9800
O2—N4	1.397 (2)	C7—H7B	0.9800
O2—H2O	0.9213	C7—H7C	0.9800
O3—C18	1.272 (3)	C8—C9	1.508 (3)
O4—N8	1.404 (2)	C9—C10	1.495 (3)
O4—H4O	0.9287	C10—H10A	0.9800
O5—H5P	0.9140	C10—H10B	0.9800
O5—H5O	0.8626	C10—H10C	0.9800
O6—H6O	0.9154	C11—C12	1.398 (4)
O6—H6P	0.9335	C11—H11	0.9500
N1—C5	1.342 (3)	C12—C13	1.367 (4)
N1—C1	1.343 (3)	C12—H12	0.9500
N2—C6	1.287 (3)	C13—C14	1.388 (4)
N2—N3	1.385 (2)	C13—H13	0.9500
N3—C8	1.337 (3)	C14—C15	1.404 (3)
N4—C9	1.284 (3)	C14—H14	0.9500
N5—C11	1.327 (3)	C15—C16	1.475 (3)
N5—C15	1.357 (3)	C16—C17	1.492 (3)
N6—C16	1.287 (3)	C17—H17A	0.9800
N6—N7	1.387 (3)	C17—H17B	0.9800
N7—C18	1.325 (3)	C17—H17C	0.9800
N8—C19	1.274 (3)	C18—C19	1.508 (3)
C1—C2	1.398 (4)	C19—C20	1.491 (3)
C1—H1	0.9500	C20—H20A	0.9800
C2—C3	1.375 (4)	C20—H20B	0.9800
C2—H2	0.9500	C20—H20C	0.9800
N2—Zn1—N6	162.52 (7)	C6—C7—H7A	109.5
N2—Zn1—O1	76.10 (7)	C6—C7—H7B	109.5
N6—Zn1—O1	121.37 (7)	H7A—C7—H7B	109.5
N2—Zn1—O3	105.12 (7)	C6—C7—H7C	109.5
N6—Zn1—O3	74.17 (6)	H7A—C7—H7C	109.5
O1—Zn1—O3	96.43 (6)	H7B—C7—H7C	109.5
N2—Zn1—N5	106.20 (7)	O1—C8—N3	127.01 (19)
N6—Zn1—N5	75.07 (7)	O1—C8—C9	117.25 (19)
O1—Zn1—N5	93.88 (7)	N3—C8—C9	115.72 (19)
O3—Zn1—N5	148.54 (7)	N4—C9—C10	124.75 (19)
N2—Zn1—N1	73.97 (7)	N4—C9—C8	116.43 (19)
N6—Zn1—N1	88.55 (7)	C10—C9—C8	118.82 (19)
O1—Zn1—N1	150.07 (7)	C9—C10—H10A	109.5
O3—Zn1—N1	90.90 (6)	C9—C10—H10B	109.5
N5—Zn1—N1	94.81 (7)	H10A—C10—H10B	109.5
C8—O1—Zn1	111.22 (13)	C9—C10—H10C	109.5
N4—O2—H2O	103.0	H10A—C10—H10C	109.5
C18—O3—Zn1	110.35 (13)	H10B—C10—H10C	109.5
N8—O4—H4O	105.6	N5—C11—C12	122.6 (2)
H5P—O5—H5O	111.3	N5—C11—H11	118.7
H6O—O6—H6P	104.7	C12—C11—H11	118.7
C5—N1—C1	118.2 (2)	C13—C12—C11	118.7 (2)
C5—N1—Zn1	112.02 (14)	C13—C12—H12	120.7
C1—N1—Zn1	129.54 (18)	C11—C12—H12	120.7
C6—N2—N3	119.76 (19)	C12—C13—C14	119.8 (2)
C6—N2—Zn1	123.02 (15)	C12—C13—H13	120.1
N3—N2—Zn1	117.15 (14)	C14—C13—H13	120.1
C8—N3—N2	108.51 (18)	C13—C14—C15	118.6 (2)
C9—N4—O2	112.04 (18)	C13—C14—H14	120.7
C11—N5—C15	119.1 (2)	C15—C14—H14	120.7
C11—N5—Zn1	127.97 (17)	N5—C15—C14	121.1 (2)
C15—N5—Zn1	112.92 (14)	N5—C15—C16	116.1 (2)
C16—N6—N7	120.20 (19)	C14—C15—C16	122.7 (2)
C16—N6—Zn1	119.99 (16)	N6—C16—C15	114.0 (2)
N7—N6—Zn1	117.29 (14)	N6—C16—C17	125.2 (2)
C18—N7—N6	108.84 (18)	C15—C16—C17	120.8 (2)
C19—N8—O4	111.39 (19)	C16—C17—H17A	109.5
N1—C1—C2	122.3 (3)	C16—C17—H17B	109.5
N1—C1—H1	118.9	H17A—C17—H17B	109.5
C2—C1—H1	118.9	C16—C17—H17C	109.5
C3—C2—C1	119.1 (2)	H17A—C17—H17C	109.5
C3—C2—H2	120.5	H17B—C17—H17C	109.5
C1—C2—H2	120.5	O3—C18—N7	126.8 (2)
C2—C3—C4	119.1 (2)	O3—C18—C19	116.84 (19)
C2—C3—H3	120.4	N7—C18—C19	116.34 (19)
C4—C3—H3	120.4	N8—C19—C20	126.5 (2)
C3—C4—C5	118.7 (3)	N8—C19—C18	114.9 (2)
C3—C4—H4	120.6	C20—C19—C18	118.58 (19)
C5—C4—H4	120.6	C19—C20—H20A	109.5
N1—C5—C4	122.5 (2)	C19—C20—H20B	109.5
N1—C5—C6	116.25 (19)	H20A—C20—H20B	109.5
C4—C5—C6	121.2 (2)	C19—C20—H20C	109.5
N2—C6—C7	125.1 (2)	H20A—C20—H20C	109.5
N2—C6—C5	114.6 (2)	H20B—C20—H20C	109.5
C7—C6—C5	120.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N7i	0.92	1.89	2.801 (3)	170
O4—H4O···O5ii	0.93	1.77	2.675 (3)	164
O5—H5P···O3	0.91	1.93	2.811 (3)	161
O5—H5O···O6	0.86	2.08	2.889 (3)	157
O6—H6O···N4iii	0.92	2.12	2.934 (3)	148
O6—H6P···N8ii	0.93	2.10	2.971 (3)	154

Zn1—N2	2.061 (2)
Zn1—N6	2.085 (2)
Zn1—O1	2.0880 (15)
Zn1—O3	2.1470 (15)
Zn1—N5	2.1955 (19)
Zn1—N1	2.2877 (19)

N2—Zn1—O1	76.10 (7)
N6—Zn1—O3	74.17 (6)
N6—Zn1—N5	75.07 (7)
N2—Zn1—N1	73.97 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N7i	0.92	1.89	2.801 (3)	170
O4—H4O⋯O5ii	0.93	1.77	2.675 (3)	164
O5—H5P⋯O3	0.91	1.93	2.811 (3)	161
O5—H5O⋯O6	0.86	2.08	2.889 (3)	157
O6—H6O⋯N4iii	0.92	2.12	2.934 (3)	148
O6—H6P⋯N8ii	0.93	2.10	2.971 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) .