{2,2'-[Pyridine-3,4-diylbis(nitrilo-methyl-idyne)]diphenolato}zinc(II).

The title compound, [Zn(C(19)H(13)N(3)O(2))], has been synthesized by the reaction of Zn(ClO(4))(2)·6H(2)O and the tetra-dentate Schiff base ligand 2,2'-[pyridine-3,4-diylbis(nitrilo-methyl-idyne)]diphenol (L). The coordination geometry of the Zn(II) ion is slightly distorted square-planar, formed by two N atoms and two O atoms from the L ligand.

Related literature

For properties of transition metals complexes with Schiff base ligands, see: Aurangzeb et al. (1994 ▶); Hulme et al. (1997 ▶); Li et al. (2008 ▶); Fei & Fang (2008 ▶); Zhang & Janiak (2001 ▶). For related structures, see: Li & Zhang (2004 ▶); Chen (2005 ▶).

Experimental

Crystal data

[Zn(C19H13N3O2)]

M = 380.69

Orthorhombic,

a = 5.3563 (8) Å

b = 16.603 (2) Å

c = 17.311 (3) Å

V = 1539.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.61 mm−1

T = 293 K

0.25 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.689, T max = 0.760

7573 measured reflections

2720 independent reflections

2519 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.00

2720 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1105 Friedel pairs

Flack parameter: 0.090 (18)

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 (Sheldrick, 1998 ▶); software used to prepare material for publication: XP.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038616/hg2565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038616/hg2565Isup2.hkl

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

[Zn(C19H13N3O2)]	F(000) = 776
Mr = 380.69	Dx = 1.643 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4002 reflections
a = 5.3563 (8) Å	θ = 2.5–26.4°
b = 16.603 (2) Å	µ = 1.61 mm−1
c = 17.311 (3) Å	T = 293 K
V = 1539.5 (4) Å3	Block, colourless
Z = 4	0.25 × 0.21 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2519 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −6→6
Tmin = 0.689, Tmax = 0.760	k = −15→19
7573 measured reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.084P)2 + 0.0681P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2720 reflections	Δρmax = 0.46 e Å−3
227 parameters	Δρmin = −0.25 e Å−3
0 restraints	Absolute structure: Flack (1983), 1105 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.090 (18)

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 > 2sigma(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	0.85000 (8)	0.22279 (3)	0.81022 (2)	0.04025 (17)
O1	0.5747 (5)	0.18278 (15)	0.76293 (15)	0.0423 (6)
O2	0.8521 (6)	0.12568 (16)	0.86177 (15)	0.0439 (6)
N1	1.4213 (8)	0.4650 (2)	0.8360 (2)	0.0592 (10)
N2	1.1291 (6)	0.26236 (16)	0.85990 (15)	0.0331 (6)
N3	0.8496 (6)	0.31937 (17)	0.75595 (15)	0.0339 (6)
C1	1.3829 (8)	0.3878 (2)	0.8649 (2)	0.0455 (9)
H1	1.4879	0.3673	0.9029	0.055*
C2	1.1895 (7)	0.3421 (2)	0.83702 (19)	0.0349 (8)
C3	1.0329 (8)	0.3735 (2)	0.7803 (2)	0.0376 (8)
C4	1.0658 (9)	0.4516 (2)	0.7538 (2)	0.0474 (10)
H4	0.9551	0.4738	0.7184	0.057*
C5	1.2653 (10)	0.4959 (3)	0.7810 (3)	0.0515 (11)
H5	1.2939	0.5473	0.7617	0.062*
C6	0.5160 (7)	0.2875 (2)	0.66888 (19)	0.0390 (8)
C7	0.4547 (7)	0.2126 (2)	0.70379 (19)	0.0374 (8)
C8	0.2526 (8)	0.1694 (3)	0.6747 (2)	0.0485 (10)
H8	0.2042	0.1212	0.6976	0.058*
C9	0.1245 (9)	0.1989 (3)	0.6112 (2)	0.0531 (11)
H9	−0.0076	0.1689	0.5914	0.064*
C10	0.1841 (8)	0.2700 (3)	0.5766 (2)	0.0529 (11)
H10	0.0936	0.2880	0.5341	0.064*
C11	0.3765 (9)	0.3141 (3)	0.6046 (2)	0.0512 (10)
H11	0.4173	0.3627	0.5811	0.061*
C12	0.7065 (7)	0.3362 (2)	0.6972 (2)	0.0385 (8)
H12	0.7342	0.3849	0.6721	0.046*
C13	1.2240 (7)	0.1422 (2)	0.9337 (2)	0.0374 (8)
C14	1.0142 (8)	0.0984 (2)	0.9087 (2)	0.0383 (8)
C15	0.9911 (8)	0.0187 (2)	0.9372 (2)	0.0451 (9)
H15	0.8543	−0.0119	0.9220	0.054*
C16	1.1607 (9)	−0.0145 (3)	0.9858 (2)	0.0492 (10)
H16	1.1398	−0.0671	1.0029	0.059*
C17	1.3639 (9)	0.0297 (3)	1.0097 (2)	0.0518 (10)
H17	1.4790	0.0073	1.0438	0.062*
C18	1.3951 (8)	0.1056 (2)	0.9835 (2)	0.0453 (10)
H18	1.5350	0.1346	0.9992	0.054*
C19	1.2673 (7)	0.2216 (3)	0.9071 (2)	0.0385 (8)
H19	1.4100	0.2471	0.9255	0.046*

	U11	U22	U33	U12	U13	U23
Zn1	0.0432 (3)	0.0352 (2)	0.0423 (3)	0.00271 (19)	−0.0008 (2)	−0.00027 (18)
O1	0.0449 (16)	0.0337 (13)	0.0484 (14)	0.0016 (12)	−0.0065 (12)	0.0014 (11)
O2	0.0449 (15)	0.0393 (13)	0.0475 (14)	−0.0069 (14)	−0.0108 (14)	0.0101 (12)
N1	0.064 (3)	0.055 (2)	0.058 (2)	−0.0059 (19)	0.0026 (18)	−0.0003 (18)
N2	0.0392 (16)	0.0273 (14)	0.0327 (13)	0.0004 (13)	0.0021 (13)	−0.0018 (12)
N3	0.0388 (17)	0.0285 (14)	0.0344 (14)	0.0033 (14)	0.0027 (15)	−0.0011 (11)
C1	0.053 (2)	0.042 (2)	0.0421 (19)	−0.0040 (18)	0.0015 (18)	0.0017 (17)
C2	0.038 (2)	0.0353 (18)	0.0318 (16)	0.0032 (15)	0.0064 (14)	−0.0035 (14)
C3	0.044 (2)	0.0340 (19)	0.0344 (17)	−0.0007 (17)	0.0039 (16)	−0.0040 (14)
C4	0.063 (3)	0.033 (2)	0.046 (2)	0.0008 (18)	−0.002 (2)	0.0048 (17)
C5	0.068 (3)	0.037 (2)	0.050 (2)	−0.0088 (19)	−0.002 (2)	0.0078 (18)
C6	0.042 (2)	0.042 (2)	0.0327 (16)	0.0114 (17)	0.0012 (15)	−0.0041 (15)
C7	0.0357 (17)	0.040 (2)	0.0366 (18)	0.0141 (16)	−0.0035 (15)	−0.0083 (16)
C8	0.046 (2)	0.043 (2)	0.056 (2)	0.0089 (18)	−0.0022 (19)	−0.008 (2)
C9	0.041 (2)	0.062 (3)	0.056 (2)	0.010 (2)	−0.011 (2)	−0.023 (2)
C10	0.047 (2)	0.067 (3)	0.044 (2)	0.014 (2)	−0.0108 (18)	−0.009 (2)
C11	0.054 (3)	0.057 (2)	0.043 (2)	0.011 (2)	0.001 (2)	0.0016 (18)
C12	0.049 (2)	0.0336 (18)	0.0334 (17)	0.0095 (15)	0.0007 (16)	−0.0012 (15)
C13	0.040 (2)	0.038 (2)	0.0343 (17)	0.0016 (16)	0.0017 (16)	0.0028 (15)
C14	0.045 (2)	0.0354 (19)	0.0344 (17)	0.0032 (16)	0.0055 (17)	0.0012 (15)
C15	0.055 (2)	0.0344 (18)	0.046 (2)	−0.0066 (18)	−0.003 (2)	0.0022 (17)
C16	0.060 (3)	0.038 (2)	0.049 (2)	0.011 (2)	0.006 (2)	0.0115 (17)
C17	0.052 (3)	0.053 (2)	0.051 (2)	0.010 (2)	−0.007 (2)	0.0112 (19)
C18	0.046 (3)	0.047 (2)	0.043 (2)	0.0036 (18)	−0.0051 (18)	0.0025 (17)
C19	0.0367 (18)	0.0397 (19)	0.0392 (17)	−0.0019 (17)	−0.0026 (14)	−0.0055 (18)

Zn1—O1	1.813 (3)	C7—C8	1.393 (6)
Zn1—O2	1.843 (2)	C8—C9	1.385 (6)
Zn1—N2	1.846 (3)	C8—H8	0.9300
Zn1—N3	1.858 (3)	C9—C10	1.361 (7)
O1—C7	1.306 (4)	C9—H9	0.9300
O2—C14	1.273 (5)	C10—C11	1.354 (7)
N1—C5	1.367 (6)	C10—H10	0.9300
N1—C1	1.391 (6)	C11—H11	0.9300
N2—C19	1.294 (5)	C12—H12	0.9300
N2—C2	1.419 (5)	C13—C18	1.397 (5)
N3—C12	1.304 (4)	C13—C14	1.406 (6)
N3—C3	1.396 (5)	C13—C19	1.416 (6)
C1—C2	1.372 (6)	C14—C15	1.417 (5)
C1—H1	0.9300	C15—C16	1.355 (6)
C2—C3	1.393 (5)	C15—H15	0.9300
C3—C4	1.387 (5)	C16—C17	1.376 (6)
C4—C5	1.380 (7)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.351 (6)
C5—H5	0.9300	C17—H17	0.9300
C6—C12	1.391 (6)	C18—H18	0.9300
C6—C11	1.412 (5)	C19—H19	0.9300
C6—C7	1.421 (6)
O1—Zn1—O2	84.43 (12)	C9—C8—C7	119.4 (4)
O1—Zn1—N2	178.96 (12)	C9—C8—H8	120.3
O2—Zn1—N2	94.64 (12)	C7—C8—H8	120.3
O1—Zn1—N3	94.99 (13)	C10—C9—C8	122.6 (4)
O2—Zn1—N3	178.58 (12)	C10—C9—H9	118.7
N2—Zn1—N3	85.95 (13)	C8—C9—H9	118.7
C7—O1—Zn1	128.0 (3)	C11—C10—C9	119.3 (4)
C14—O2—Zn1	128.6 (2)	C11—C10—H10	120.3
C5—N1—C1	120.4 (4)	C9—C10—H10	120.3
C19—N2—C2	122.3 (3)	C10—C11—C6	121.0 (4)
C19—N2—Zn1	124.9 (3)	C10—C11—H11	119.5
C2—N2—Zn1	112.7 (2)	C6—C11—H11	119.5
C12—N3—C3	120.7 (3)	N3—C12—C6	125.6 (3)
C12—N3—Zn1	125.4 (3)	N3—C12—H12	117.2
C3—N3—Zn1	113.7 (2)	C6—C12—H12	117.2
C2—C1—N1	119.7 (4)	C18—C13—C14	119.4 (3)
C2—C1—H1	120.2	C18—C13—C19	119.8 (4)
N1—C1—H1	120.2	C14—C13—C19	120.8 (3)
C1—C2—C3	119.7 (4)	O2—C14—C13	123.9 (3)
C1—C2—N2	126.2 (4)	O2—C14—C15	119.7 (4)
C3—C2—N2	114.1 (3)	C13—C14—C15	116.4 (3)
C4—C3—C2	120.4 (4)	C16—C15—C14	122.5 (4)
C4—C3—N3	126.3 (4)	C16—C15—H15	118.7
C2—C3—N3	113.3 (3)	C14—C15—H15	118.7
C5—C4—C3	118.9 (4)	C15—C16—C17	120.0 (4)
C5—C4—H4	120.5	C15—C16—H16	120.0
C3—C4—H4	120.5	C17—C16—H16	120.0
N1—C5—C4	120.8 (4)	C18—C17—C16	119.6 (4)
N1—C5—H5	119.6	C18—C17—H17	120.2
C4—C5—H5	119.6	C16—C17—H17	120.2
C12—C6—C11	119.0 (4)	C17—C18—C13	122.1 (4)
C12—C6—C7	121.9 (3)	C17—C18—H18	119.0
C11—C6—C7	119.2 (4)	C13—C18—H18	119.0
O1—C7—C8	118.1 (4)	N2—C19—C13	126.8 (4)
O1—C7—C6	123.5 (3)	N2—C19—H19	116.6
C8—C7—C6	118.4 (3)	C13—C19—H19	116.6