Chlorido[2-meth-oxy-6-(2-pyridyl-methyl-imino-meth-yl)phenolato]zinc(II).

In the title mol-ecule, [Zn(C(14)H(13)N(2)O(2))Cl], the Zn(II) ion is coordinated by one O and two N atoms from the Schiff base ligand, and a chloride anion in a distorted square-planar geometry. In the crystal structure, π-π inter-actions link the approximately planar (mean deviation 0.0569 Å) mol-ecules into stacks parallel to the a axis.

Related literature

For properties of transition metal complexes with Schiff base ligands, see: Ghosh et al. (2006 ▶); Singh et al. (2007 ▶); Ward (2007 ▶). For details of the synthesis of the ligand, see Kannappan et al. (2005 ▶). For related structures, see: Li & Zhang (2004 ▶); Chen (2005 ▶); You (2005 ▶).

Experimental

Crystal data

[Zn(C14H13N2O2)Cl]

M = 342.08

Monoclinic,

a = 7.1013 (5) Å

b = 18.2673 (14) Å

c = 10.3241 (8) Å

β = 104.789 (1)°

V = 1294.89 (17) Å3

Z = 4

Mo Kα radiation

μ = 2.10 mm−1

T = 293 K

0.31 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.562, T max = 0.643

6845 measured reflections

2538 independent reflections

2263 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.082

S = 1.06

2538 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 e Å−3

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/S1600536809037015/cv2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037015/cv2598Isup2.hkl

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

[Zn(C14H13N2O2)Cl]	F(000) = 696
Mr = 342.08	Dx = 1.755 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1013 (5) Å	Cell parameters from 3850 reflections
b = 18.2673 (14) Å	θ = 3.0–26.0°
c = 10.3241 (8) Å	µ = 2.10 mm−1
β = 104.789 (1)°	T = 293 K
V = 1294.89 (17) Å3	Block, colourless
Z = 4	0.31 × 0.25 × 0.23 mm

Bruker APEXII CCD area-detector diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	2263 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.562, Tmax = 0.643	k = −18→22
6845 measured reflections	l = −12→10

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.6563P] where P = (Fo2 + 2Fc2)/3
2538 reflections	(Δ/σ)max = 0.006
182 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.31 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	0.33329 (4)	0.484815 (14)	0.11005 (3)	0.02880 (12)
Cl1	0.45273 (10)	0.40303 (3)	0.27143 (6)	0.04062 (17)
O1	0.2046 (2)	0.40698 (8)	−0.00080 (16)	0.0324 (4)
O2	0.0568 (3)	0.28355 (9)	−0.10946 (17)	0.0389 (4)
N1	0.4516 (3)	0.57415 (10)	0.21313 (18)	0.0272 (4)
N2	0.2579 (3)	0.55672 (10)	−0.03049 (19)	0.0276 (4)
C1	0.0718 (3)	0.47592 (12)	−0.2000 (2)	0.0282 (5)
C2	0.1050 (3)	0.41075 (12)	−0.1239 (2)	0.0265 (5)
C3	0.0236 (3)	0.34459 (12)	−0.1884 (2)	0.0295 (5)
C4	−0.0793 (3)	0.34472 (14)	−0.3194 (2)	0.0334 (5)
H4	−0.1296	0.3011	−0.3605	0.040*
C5	−0.1094 (3)	0.40998 (15)	−0.3922 (2)	0.0356 (5)
H5	−0.1803	0.4094	−0.4814	0.043*
C6	−0.0367 (3)	0.47439 (13)	−0.3345 (2)	0.0325 (5)
H6	−0.0588	0.5175	−0.3840	0.039*
C7	0.1495 (3)	0.54479 (13)	−0.1478 (2)	0.0303 (5)
H7	0.1183	0.5850	−0.2046	0.036*
C8	−0.0093 (4)	0.21497 (13)	−0.1699 (3)	0.0433 (6)
H8A	−0.1460	0.2180	−0.2128	0.065*
H8B	0.0128	0.1776	−0.1024	0.065*
H8C	0.0608	0.2032	−0.2353	0.065*
C9	0.4324 (3)	0.63695 (12)	0.1444 (2)	0.0281 (5)
C10	0.5065 (3)	0.70331 (13)	0.2015 (3)	0.0340 (5)
H10	0.4936	0.7456	0.1499	0.041*
C11	0.5983 (4)	0.70499 (14)	0.3345 (3)	0.0388 (6)
H11	0.6496	0.7484	0.3760	0.047*
C12	0.6133 (4)	0.64061 (15)	0.4060 (3)	0.0393 (6)
H12	0.6722	0.6406	0.4974	0.047*
C13	0.5419 (3)	0.57673 (14)	0.3432 (2)	0.0338 (5)
H13	0.5569	0.5337	0.3929	0.041*
C14	0.3226 (4)	0.63242 (12)	0.0026 (2)	0.0325 (5)
H14A	0.2104	0.6646	−0.0133	0.039*
H14B	0.4045	0.6481	−0.0543	0.039*

	U11	U22	U33	U12	U13	U23
Zn1	0.03695 (18)	0.02365 (17)	0.02486 (17)	0.00029 (10)	0.00615 (12)	0.00196 (10)
Cl1	0.0635 (4)	0.0280 (3)	0.0268 (3)	0.0019 (3)	0.0049 (3)	0.0074 (2)
O1	0.0444 (9)	0.0229 (8)	0.0246 (8)	−0.0019 (7)	−0.0010 (7)	0.0024 (6)
O2	0.0494 (10)	0.0228 (8)	0.0374 (9)	−0.0037 (7)	−0.0017 (8)	−0.0012 (7)
N1	0.0300 (9)	0.0251 (9)	0.0270 (9)	0.0010 (7)	0.0082 (8)	0.0000 (8)
N2	0.0343 (10)	0.0211 (9)	0.0271 (9)	0.0011 (8)	0.0073 (8)	0.0032 (7)
C1	0.0271 (11)	0.0309 (12)	0.0257 (11)	0.0035 (9)	0.0051 (9)	0.0031 (9)
C2	0.0238 (10)	0.0285 (11)	0.0263 (11)	0.0013 (9)	0.0051 (8)	−0.0008 (9)
C3	0.0291 (11)	0.0269 (11)	0.0322 (12)	0.0013 (9)	0.0076 (9)	−0.0007 (9)
C4	0.0316 (12)	0.0368 (13)	0.0306 (12)	−0.0017 (10)	0.0057 (10)	−0.0078 (10)
C5	0.0311 (12)	0.0480 (15)	0.0250 (12)	0.0023 (11)	0.0022 (9)	−0.0006 (10)
C6	0.0336 (12)	0.0365 (13)	0.0256 (11)	0.0040 (10)	0.0043 (10)	0.0052 (10)
C7	0.0356 (12)	0.0272 (12)	0.0273 (11)	0.0044 (9)	0.0069 (9)	0.0067 (10)
C8	0.0450 (15)	0.0260 (12)	0.0523 (16)	−0.0036 (10)	0.0002 (12)	−0.0053 (11)
C9	0.0294 (11)	0.0247 (11)	0.0322 (12)	0.0003 (9)	0.0119 (9)	−0.0015 (9)
C10	0.0365 (12)	0.0254 (11)	0.0415 (13)	−0.0019 (10)	0.0128 (10)	−0.0028 (10)
C11	0.0344 (12)	0.0363 (13)	0.0463 (14)	−0.0088 (11)	0.0116 (11)	−0.0129 (12)
C12	0.0348 (12)	0.0480 (15)	0.0338 (13)	−0.0062 (11)	0.0062 (10)	−0.0084 (11)
C13	0.0354 (12)	0.0358 (12)	0.0286 (12)	−0.0022 (10)	0.0052 (10)	0.0017 (10)
C14	0.0490 (14)	0.0183 (10)	0.0304 (12)	0.0009 (9)	0.0106 (10)	0.0022 (9)

Zn1—O1	1.9059 (16)	C5—C6	1.360 (4)
Zn1—N2	1.9288 (18)	C5—H5	0.9300
Zn1—N1	2.0112 (19)	C6—H6	0.9300
Zn1—Cl1	2.2373 (6)	C7—H7	0.9300
O1—C2	1.289 (3)	C8—H8A	0.9600
O2—C3	1.366 (3)	C8—H8B	0.9600
O2—C8	1.425 (3)	C8—H8C	0.9600
N1—C13	1.333 (3)	C9—C10	1.391 (3)
N1—C9	1.337 (3)	C9—C14	1.475 (3)
N2—C7	1.277 (3)	C10—C11	1.362 (4)
N2—C14	1.470 (3)	C10—H10	0.9300
C1—C6	1.406 (3)	C11—C12	1.378 (4)
C1—C2	1.412 (3)	C11—H11	0.9300
C1—C7	1.423 (3)	C12—C13	1.368 (4)
C2—C3	1.429 (3)	C12—H12	0.9300
C3—C4	1.363 (3)	C13—H13	0.9300
C4—C5	1.396 (4)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
Cg1···Cg2i	3.566 (4)	Cg1···Cg2ii	3.767 (7)
O1—Zn1—N2	93.32 (7)	C1—C6—H6	120.0
O1—Zn1—N1	174.02 (7)	N2—C7—C1	126.3 (2)
N2—Zn1—N1	81.01 (8)	N2—C7—H7	116.9
O1—Zn1—Cl1	88.94 (5)	C1—C7—H7	116.9
N2—Zn1—Cl1	173.99 (6)	O2—C8—H8A	109.5
N1—Zn1—Cl1	96.89 (6)	O2—C8—H8B	109.5
C2—O1—Zn1	127.63 (14)	H8A—C8—H8B	109.5
C3—O2—C8	117.96 (19)	O2—C8—H8C	109.5
C13—N1—C9	117.5 (2)	H8A—C8—H8C	109.5
C13—N1—Zn1	126.18 (16)	H8B—C8—H8C	109.5
C9—N1—Zn1	116.30 (15)	N1—C9—C10	123.1 (2)
C7—N2—C14	117.25 (19)	N1—C9—C14	115.78 (19)
C7—N2—Zn1	125.56 (16)	C10—C9—C14	121.1 (2)
C14—N2—Zn1	117.11 (14)	C11—C10—C9	118.6 (2)
C6—C1—C2	120.3 (2)	C11—C10—H10	120.7
C6—C1—C7	117.0 (2)	C9—C10—H10	120.7
C2—C1—C7	122.7 (2)	C10—C11—C12	118.2 (2)
O1—C2—C1	124.4 (2)	C10—C11—H11	120.9
O1—C2—C3	118.0 (2)	C12—C11—H11	120.9
C1—C2—C3	117.6 (2)	C13—C12—C11	120.4 (2)
C4—C3—O2	124.1 (2)	C13—C12—H12	119.8
C4—C3—C2	120.8 (2)	C11—C12—H12	119.8
O2—C3—C2	115.12 (19)	N1—C13—C12	122.2 (2)
C3—C4—C5	120.4 (2)	N1—C13—H13	118.9
C3—C4—H4	119.8	C12—C13—H13	118.9
C5—C4—H4	119.8	N2—C14—C9	109.77 (18)
C6—C5—C4	120.9 (2)	N2—C14—H14A	109.7
C6—C5—H5	119.5	C9—C14—H14A	109.7
C4—C5—H5	119.5	N2—C14—H14B	109.7
C5—C6—C1	120.1 (2)	C9—C14—H14B	109.7
C5—C6—H6	120.0	H14A—C14—H14B	108.2

Zn1—O1	1.9059 (16)
Zn1—N2	1.9288 (18)
Zn1—N1	2.0112 (19)
Zn1—Cl1	2.2373 (6)

Cg1⋯Cg2i	3.566 (4)
Cg1⋯Cg2ii	3.767 (7)

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are centroids of atoms C1–C6 and N1/C9–C13, respectively.