Dichlorido[2,2'-(oxydimethyl-ene)dipyridine]zinc(II).

In the title complex, [ZnCl(2)(C(12)H(12)N(2)O)], the Zn(II) atom is coordinated in a distorted trigonal-bipyramidal geometry by two Cl atoms, and one O atom and two N atoms from the 2,2'-(oxydimethyl-ene)dipyridine ligand. In the complex, the two pyridine rings make a dihedral angle of 15.44 (14)°. There is a weak inter-molecular π-π stacking inter-action between pyridine rings; the centroid-centroid distance is 3.8079 (17) Å.

Related literature

For the isotypic Cd and Cu analogs of the title compound, see: Li (2007 ▶) and Li (2008 ▶), respectively.

Experimental

Crystal data

[ZnCl2(C12H12N2O)]

M = 336.51

Monoclinic,

a = 8.0874 (12) Å

b = 12.5013 (18) Å

c = 15.6210 (16) Å

β = 121.180 (11)°

V = 1351.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.20 mm−1

T = 298 (2) K

0.40 × 0.32 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.466, T max = 0.751

5529 measured reflections

2388 independent reflections

2158 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.069

S = 1.05

2388 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808034600/is2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034600/is2347Isup2.hkl

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

[ZnCl2(C12H12N2O)]	F(000) = 680
Mr = 336.51	Dx = 1.654 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3915 reflections
a = 8.0874 (12) Å	θ = 2.9–28.1°
b = 12.5013 (18) Å	µ = 2.20 mm−1
c = 15.6210 (16) Å	T = 298 K
β = 121.180 (11)°	Block, colorless
V = 1351.2 (3) Å3	0.40 × 0.32 × 0.13 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2388 independent reflections
Radiation source: fine-focus sealed tube	2158 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.466, Tmax = 0.751	k = −14→8
5529 measured reflections	l = −17→18

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.2883P] where P = (Fo2 + 2Fc2)/3
2388 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.35 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
C1	0.4107 (3)	0.83139 (18)	−0.04103 (18)	0.0431 (5)
C2	0.2717 (3)	0.9110 (2)	−0.0806 (2)	0.0609 (7)
H2	0.2077	0.9271	−0.1485	0.073*
C3	0.4597 (4)	0.8595 (2)	0.1155 (2)	0.0560 (6)
H3	0.5236	0.8417	0.1831	0.067*
C4	0.3238 (4)	0.9395 (2)	0.0809 (3)	0.0687 (8)
H4	0.2964	0.9752	0.1243	0.082*
C5	0.2299 (4)	0.9658 (2)	−0.0178 (3)	0.0698 (8)
H5	0.1384	1.0203	−0.0425	0.084*
C6	0.4609 (3)	0.7685 (2)	−0.10595 (18)	0.0503 (6)
H6A	0.3458	0.7537	−0.1702	0.060*
H6B	0.5515	0.8079	−0.1171	0.060*
C7	0.6087 (3)	0.59950 (19)	−0.09923 (16)	0.0460 (5)
H7A	0.6875	0.6357	−0.1205	0.055*
H7B	0.4990	0.5673	−0.1575	0.055*
C8	0.7246 (3)	0.51540 (18)	−0.02358 (16)	0.0397 (5)
C9	0.7807 (3)	0.4226 (2)	−0.05024 (19)	0.0495 (6)
H9	0.7444	0.4107	−0.1165	0.059*
C10	0.8902 (4)	0.3486 (2)	0.0219 (2)	0.0537 (6)
H10	0.9305	0.2863	0.0054	0.064*
C11	0.9394 (3)	0.36760 (19)	0.1189 (2)	0.0508 (6)
H11	1.0125	0.3182	0.1690	0.061*
C12	0.8788 (3)	0.46096 (18)	0.14068 (18)	0.0456 (5)
H12	0.9123	0.4736	0.2064	0.055*
Cl1	0.71768 (8)	0.63978 (5)	0.25220 (4)	0.04925 (16)
Cl2	0.98849 (8)	0.77735 (5)	0.14453 (5)	0.05218 (16)
N1	0.5035 (3)	0.80611 (14)	0.05554 (14)	0.0426 (4)
N2	0.7730 (2)	0.53478 (14)	0.07069 (13)	0.0386 (4)
O1	0.5448 (3)	0.67253 (13)	−0.05431 (12)	0.0539 (4)
Zn1	0.71979 (3)	0.686250 (19)	0.111610 (17)	0.03705 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0374 (11)	0.0391 (12)	0.0482 (14)	−0.0003 (9)	0.0189 (10)	0.0079 (10)
C2	0.0492 (14)	0.0550 (15)	0.0680 (17)	0.0116 (12)	0.0229 (13)	0.0196 (14)
C3	0.0644 (15)	0.0483 (14)	0.0592 (16)	0.0069 (12)	0.0346 (13)	−0.0003 (12)
C4	0.0747 (18)	0.0504 (16)	0.094 (2)	0.0070 (14)	0.0533 (18)	−0.0080 (16)
C5	0.0595 (16)	0.0487 (15)	0.104 (2)	0.0156 (13)	0.0439 (17)	0.0120 (16)
C6	0.0497 (13)	0.0538 (14)	0.0417 (13)	0.0048 (11)	0.0196 (10)	0.0125 (11)
C7	0.0496 (12)	0.0524 (14)	0.0371 (12)	−0.0020 (11)	0.0232 (10)	−0.0055 (11)
C8	0.0393 (11)	0.0425 (12)	0.0393 (12)	−0.0079 (9)	0.0217 (9)	−0.0068 (10)
C9	0.0547 (13)	0.0495 (14)	0.0519 (14)	−0.0101 (11)	0.0329 (12)	−0.0153 (12)
C10	0.0568 (14)	0.0395 (12)	0.0784 (19)	−0.0017 (11)	0.0444 (14)	−0.0067 (13)
C11	0.0491 (13)	0.0425 (13)	0.0603 (16)	0.0047 (10)	0.0281 (12)	0.0069 (11)
C12	0.0471 (12)	0.0437 (13)	0.0430 (13)	0.0021 (10)	0.0213 (10)	0.0012 (10)
Cl1	0.0624 (3)	0.0501 (3)	0.0403 (3)	−0.0039 (3)	0.0301 (3)	0.0019 (3)
Cl2	0.0507 (3)	0.0541 (3)	0.0561 (4)	−0.0081 (3)	0.0307 (3)	−0.0034 (3)
N1	0.0420 (10)	0.0387 (10)	0.0445 (11)	0.0025 (8)	0.0206 (9)	0.0011 (8)
N2	0.0419 (9)	0.0362 (9)	0.0380 (10)	−0.0004 (7)	0.0208 (8)	−0.0025 (8)
O1	0.0673 (10)	0.0512 (10)	0.0332 (9)	0.0166 (8)	0.0190 (8)	0.0023 (7)
Zn1	0.04082 (16)	0.03641 (17)	0.03043 (17)	0.00126 (10)	0.01599 (12)	−0.00073 (10)

C1—N1	1.329 (3)	C7—H7B	0.9700
C1—C2	1.384 (3)	C8—N2	1.336 (3)
C1—C6	1.496 (3)	C8—C9	1.386 (3)
C2—C5	1.375 (4)	C9—C10	1.370 (4)
C2—H2	0.9300	C9—H9	0.9300
C3—N1	1.339 (3)	C10—C11	1.373 (4)
C3—C4	1.373 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.375 (3)
C4—C5	1.360 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—N2	1.346 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—O1	1.409 (3)	Cl1—Zn1	2.2803 (6)
C6—H6A	0.9700	Cl2—Zn1	2.2642 (7)
C6—H6B	0.9700	N1—Zn1	2.1178 (18)
C7—O1	1.403 (3)	N2—Zn1	2.1128 (18)
C7—C8	1.494 (3)	O1—Zn1	2.2252 (16)
C7—H7A	0.9700
N1—C1—C2	121.9 (2)	C10—C9—H9	120.3
N1—C1—C6	116.90 (19)	C8—C9—H9	120.3
C2—C1—C6	121.2 (2)	C9—C10—C11	119.0 (2)
C5—C2—C1	118.8 (3)	C9—C10—H10	120.5
C5—C2—H2	120.6	C11—C10—H10	120.5
C1—C2—H2	120.6	C10—C11—C12	118.9 (2)
N1—C3—C4	122.4 (3)	C10—C11—H11	120.5
N1—C3—H3	118.8	C12—C11—H11	120.5
C4—C3—H3	118.8	N2—C12—C11	122.6 (2)
C5—C4—C3	119.1 (3)	N2—C12—H12	118.7
C5—C4—H4	120.5	C11—C12—H12	118.7
C3—C4—H4	120.5	C1—N1—C3	118.5 (2)
C4—C5—C2	119.3 (2)	C1—N1—Zn1	119.86 (15)
C4—C5—H5	120.4	C3—N1—Zn1	121.64 (17)
C2—C5—H5	120.4	C8—N2—C12	118.13 (19)
O1—C6—C1	106.18 (18)	C8—N2—Zn1	120.46 (14)
O1—C6—H6A	110.5	C12—N2—Zn1	120.81 (15)
C1—C6—H6A	110.5	C7—O1—C6	117.43 (18)
O1—C6—H6B	110.5	C7—O1—Zn1	117.11 (13)
C1—C6—H6B	110.5	C6—O1—Zn1	115.38 (14)
H6A—C6—H6B	108.7	N2—Zn1—N1	139.71 (7)
O1—C7—C8	107.76 (17)	N2—Zn1—O1	71.63 (6)
O1—C7—H7A	110.2	N1—Zn1—O1	71.44 (7)
C8—C7—H7A	110.2	N2—Zn1—Cl2	101.41 (5)
O1—C7—H7B	110.2	N1—Zn1—Cl2	103.18 (5)
C8—C7—H7B	110.2	O1—Zn1—Cl2	105.09 (5)
H7A—C7—H7B	108.5	N2—Zn1—Cl1	99.63 (5)
N2—C8—C9	121.9 (2)	N1—Zn1—Cl1	99.33 (6)
N2—C8—C7	116.73 (19)	O1—Zn1—Cl1	141.69 (5)
C9—C8—C7	121.4 (2)	Cl2—Zn1—Cl1	113.22 (3)
C10—C9—C8	119.4 (2)
N1—C1—C2—C5	0.5 (4)	C8—C7—O1—Zn1	25.3 (2)
C6—C1—C2—C5	179.5 (2)	C1—C6—O1—C7	−178.79 (18)
N1—C3—C4—C5	0.0 (4)	C1—C6—O1—Zn1	−34.2 (2)
C3—C4—C5—C2	0.7 (4)	C8—N2—Zn1—N1	40.8 (2)
C1—C2—C5—C4	−0.9 (4)	C12—N2—Zn1—N1	−148.24 (15)
N1—C1—C6—O1	20.9 (3)	C8—N2—Zn1—O1	16.36 (15)
C2—C1—C6—O1	−158.1 (2)	C12—N2—Zn1—O1	−172.68 (17)
O1—C7—C8—N2	−11.5 (3)	C8—N2—Zn1—Cl2	−85.92 (15)
O1—C7—C8—C9	169.19 (19)	C12—N2—Zn1—Cl2	85.04 (16)
N2—C8—C9—C10	−0.5 (3)	C8—N2—Zn1—Cl1	157.83 (14)
C7—C8—C9—C10	178.7 (2)	C12—N2—Zn1—Cl1	−31.21 (16)
C8—C9—C10—C11	0.9 (3)	C1—N1—Zn1—N2	−40.5 (2)
C9—C10—C11—C12	−0.6 (3)	C3—N1—Zn1—N2	140.93 (17)
C10—C11—C12—N2	−0.1 (4)	C1—N1—Zn1—O1	−16.06 (16)
C2—C1—N1—C3	0.2 (3)	C3—N1—Zn1—O1	165.40 (19)
C6—C1—N1—C3	−178.8 (2)	C1—N1—Zn1—Cl2	85.67 (16)
C2—C1—N1—Zn1	−178.39 (17)	C3—N1—Zn1—Cl2	−92.87 (18)
C6—C1—N1—Zn1	2.6 (3)	C1—N1—Zn1—Cl1	−157.66 (16)
C4—C3—N1—C1	−0.5 (4)	C3—N1—Zn1—Cl1	23.80 (18)
C4—C3—N1—Zn1	178.1 (2)	C7—O1—Zn1—N2	−23.24 (15)
C9—C8—N2—C12	−0.2 (3)	C6—O1—Zn1—N2	−167.91 (17)
C7—C8—N2—C12	−179.44 (19)	C7—O1—Zn1—N1	173.15 (17)
C9—C8—N2—Zn1	171.03 (15)	C6—O1—Zn1—N1	28.48 (15)
C7—C8—N2—Zn1	−8.2 (2)	C7—O1—Zn1—Cl2	74.03 (16)
C11—C12—N2—C8	0.5 (3)	C6—O1—Zn1—Cl2	−70.65 (16)
C11—C12—N2—Zn1	−170.71 (17)	C7—O1—Zn1—Cl1	−105.42 (16)
C8—C7—O1—C6	169.28 (19)	C6—O1—Zn1—Cl1	109.91 (15)

Table 1

Selected bond lengths (Å)

Cl1—Zn1	2.2803 (6)
Cl2—Zn1	2.2642 (7)
N1—Zn1	2.1178 (18)
N2—Zn1	2.1128 (18)
O1—Zn1	2.2252 (16)