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Acta Cryst. (2008). E64, m1468    [ doi:10.1107/S1600536808034600 ]

Dichlorido[2,2'-(oxydimethylene)dipyridine]zinc(II)

J. Li

Abstract top

In the title complex, [ZnCl2(C12H12N2O)], the ZnII 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'-(oxydimethylene)dipyridine ligand. In the complex, the two pyridine rings make a dihedral angle of 15.44 (14)°. There is a weak intermolecular [pi]-[pi] stacking interaction between pyridine rings; the centroid-centroid distance is 3.8079 (17) Å.

Comment top

2,2'-(oxydimethylene)dipyridine is an useful tridentate terminal ligand and the CdII complex with it as ligand has been published (Li, 2007). Herein the crystal structure of the title Zn complex, (I), with 2,2'-(oxydimethylene)dipyridine as ligand, is reported.

The molecular structure of (I) is shown in Fig. 1. In this mononuclear complex, atom Zn1 is in a distorted trigonal bipyramidal coordination environment (Table 1). In the crystal structure, there are a weak π-π stacking interaction between symmetry related pyridyl rings, with the relevant distances being Cg1···Cg1i = 3.8079 (17) Å and a perpendicular distance of 3.597 Å [symmetry code (i) 1-x, 2-y, -z; Cg1 is the centroid of the N1/C1—C5 ring]. The title compound is isostructural with the CdII complex (Li, 2007).

Related literature top

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

Experimental top

A methanol solution (5 ml) of 2,2'-(oxydimethylene)dipyridine (0.0345 g, 0.172 mmol) was added into 8 ml H2O solution containing ZnCl2 (0.0241 g, 0.177 mmol). The mixed solution was stirred for a few minutes. The colorless single crystals were obtained after the solution had been allowed to stand at room temperature for two weeks.

Refinement top

All H atom were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of complex (I), showing the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level
Dichlorido[2,2'-(oxydimethylene)dipyridine]zinc(II) top
Crystal data top
[ZnCl2(C12H12N2O)]F(000) = 680
Mr = 336.51Dx = 1.654 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3915 reflections
a = 8.0874 (12) Åθ = 2.9–28.1°
b = 12.5013 (18) ŵ = 2.20 mm−1
c = 15.6210 (16) ÅT = 298 K
β = 121.180 (11)°Block, colorless
V = 1351.2 (3) Å30.40 × 0.32 × 0.13 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2388 independent reflections
Radiation source: fine-focus sealed tube2158 reflections with I > 2σ(I)
graphiteRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→9
Tmin = 0.466, Tmax = 0.751k = −14→8
5529 measured reflectionsl = −17→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-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 parametersΔρmax = 0.51 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[ZnCl2(C12H12N2O)]V = 1351.2 (3) Å3
Mr = 336.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0874 (12) ŵ = 2.20 mm−1
b = 12.5013 (18) ÅT = 298 K
c = 15.6210 (16) Å0.40 × 0.32 × 0.13 mm
β = 121.180 (11)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2388 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2158 reflections with I > 2σ(I)
Tmin = 0.466, Tmax = 0.751Rint = 0.024
5529 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.51 e Å−3
S = 1.05Δρmin = −0.35 e Å−3
2388 reflectionsAbsolute structure: ?
163 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4107 (3)0.83139 (18)−0.04103 (18)0.0431 (5)
C20.2717 (3)0.9110 (2)−0.0806 (2)0.0609 (7)
H20.20770.9271−0.14850.073*
C30.4597 (4)0.8595 (2)0.1155 (2)0.0560 (6)
H30.52360.84170.18310.067*
C40.3238 (4)0.9395 (2)0.0809 (3)0.0687 (8)
H40.29640.97520.12430.082*
C50.2299 (4)0.9658 (2)−0.0178 (3)0.0698 (8)
H50.13841.0203−0.04250.084*
C60.4609 (3)0.7685 (2)−0.10595 (18)0.0503 (6)
H6A0.34580.7537−0.17020.060*
H6B0.55150.8079−0.11710.060*
C70.6087 (3)0.59950 (19)−0.09923 (16)0.0460 (5)
H7A0.68750.6357−0.12050.055*
H7B0.49900.5673−0.15750.055*
C80.7246 (3)0.51540 (18)−0.02358 (16)0.0397 (5)
C90.7807 (3)0.4226 (2)−0.05024 (19)0.0495 (6)
H90.74440.4107−0.11650.059*
C100.8902 (4)0.3486 (2)0.0219 (2)0.0537 (6)
H100.93050.28630.00540.064*
C110.9394 (3)0.36760 (19)0.1189 (2)0.0508 (6)
H111.01250.31820.16900.061*
C120.8788 (3)0.46096 (18)0.14068 (18)0.0456 (5)
H120.91230.47360.20640.055*
Cl10.71768 (8)0.63978 (5)0.25220 (4)0.04925 (16)
Cl20.98849 (8)0.77735 (5)0.14453 (5)0.05218 (16)
N10.5035 (3)0.80611 (14)0.05554 (14)0.0426 (4)
N20.7730 (2)0.53478 (14)0.07069 (13)0.0386 (4)
O10.5448 (3)0.67253 (13)−0.05431 (12)0.0539 (4)
Zn10.71979 (3)0.686250 (19)0.111610 (17)0.03705 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0374 (11)0.0391 (12)0.0482 (14)−0.0003 (9)0.0189 (10)0.0079 (10)
C20.0492 (14)0.0550 (15)0.0680 (17)0.0116 (12)0.0229 (13)0.0196 (14)
C30.0644 (15)0.0483 (14)0.0592 (16)0.0069 (12)0.0346 (13)−0.0003 (12)
C40.0747 (18)0.0504 (16)0.094 (2)0.0070 (14)0.0533 (18)−0.0080 (16)
C50.0595 (16)0.0487 (15)0.104 (2)0.0156 (13)0.0439 (17)0.0120 (16)
C60.0497 (13)0.0538 (14)0.0417 (13)0.0048 (11)0.0196 (10)0.0125 (11)
C70.0496 (12)0.0524 (14)0.0371 (12)−0.0020 (11)0.0232 (10)−0.0055 (11)
C80.0393 (11)0.0425 (12)0.0393 (12)−0.0079 (9)0.0217 (9)−0.0068 (10)
C90.0547 (13)0.0495 (14)0.0519 (14)−0.0101 (11)0.0329 (12)−0.0153 (12)
C100.0568 (14)0.0395 (12)0.0784 (19)−0.0017 (11)0.0444 (14)−0.0067 (13)
C110.0491 (13)0.0425 (13)0.0603 (16)0.0047 (10)0.0281 (12)0.0069 (11)
C120.0471 (12)0.0437 (13)0.0430 (13)0.0021 (10)0.0213 (10)0.0012 (10)
Cl10.0624 (3)0.0501 (3)0.0403 (3)−0.0039 (3)0.0301 (3)0.0019 (3)
Cl20.0507 (3)0.0541 (3)0.0561 (4)−0.0081 (3)0.0307 (3)−0.0034 (3)
N10.0420 (10)0.0387 (10)0.0445 (11)0.0025 (8)0.0206 (9)0.0011 (8)
N20.0419 (9)0.0362 (9)0.0380 (10)−0.0004 (7)0.0208 (8)−0.0025 (8)
O10.0673 (10)0.0512 (10)0.0332 (9)0.0166 (8)0.0190 (8)0.0023 (7)
Zn10.04082 (16)0.03641 (17)0.03043 (17)0.00126 (10)0.01599 (12)−0.00073 (10)
Geometric parameters (Å, °) top
C1—N11.329 (3)C7—H7B0.9700
C1—C21.384 (3)C8—N21.336 (3)
C1—C61.496 (3)C8—C91.386 (3)
C2—C51.375 (4)C9—C101.370 (4)
C2—H20.9300C9—H90.9300
C3—N11.339 (3)C10—C111.373 (4)
C3—C41.373 (4)C10—H100.9300
C3—H30.9300C11—C121.375 (3)
C4—C51.360 (4)C11—H110.9300
C4—H40.9300C12—N21.346 (3)
C5—H50.9300C12—H120.9300
C6—O11.409 (3)Cl1—Zn12.2803 (6)
C6—H6A0.9700Cl2—Zn12.2642 (7)
C6—H6B0.9700N1—Zn12.1178 (18)
C7—O11.403 (3)N2—Zn12.1128 (18)
C7—C81.494 (3)O1—Zn12.2252 (16)
C7—H7A0.9700
N1—C1—C2121.9 (2)C10—C9—H9120.3
N1—C1—C6116.90 (19)C8—C9—H9120.3
C2—C1—C6121.2 (2)C9—C10—C11119.0 (2)
C5—C2—C1118.8 (3)C9—C10—H10120.5
C5—C2—H2120.6C11—C10—H10120.5
C1—C2—H2120.6C10—C11—C12118.9 (2)
N1—C3—C4122.4 (3)C10—C11—H11120.5
N1—C3—H3118.8C12—C11—H11120.5
C4—C3—H3118.8N2—C12—C11122.6 (2)
C5—C4—C3119.1 (3)N2—C12—H12118.7
C5—C4—H4120.5C11—C12—H12118.7
C3—C4—H4120.5C1—N1—C3118.5 (2)
C4—C5—C2119.3 (2)C1—N1—Zn1119.86 (15)
C4—C5—H5120.4C3—N1—Zn1121.64 (17)
C2—C5—H5120.4C8—N2—C12118.13 (19)
O1—C6—C1106.18 (18)C8—N2—Zn1120.46 (14)
O1—C6—H6A110.5C12—N2—Zn1120.81 (15)
C1—C6—H6A110.5C7—O1—C6117.43 (18)
O1—C6—H6B110.5C7—O1—Zn1117.11 (13)
C1—C6—H6B110.5C6—O1—Zn1115.38 (14)
H6A—C6—H6B108.7N2—Zn1—N1139.71 (7)
O1—C7—C8107.76 (17)N2—Zn1—O171.63 (6)
O1—C7—H7A110.2N1—Zn1—O171.44 (7)
C8—C7—H7A110.2N2—Zn1—Cl2101.41 (5)
O1—C7—H7B110.2N1—Zn1—Cl2103.18 (5)
C8—C7—H7B110.2O1—Zn1—Cl2105.09 (5)
H7A—C7—H7B108.5N2—Zn1—Cl199.63 (5)
N2—C8—C9121.9 (2)N1—Zn1—Cl199.33 (6)
N2—C8—C7116.73 (19)O1—Zn1—Cl1141.69 (5)
C9—C8—C7121.4 (2)Cl2—Zn1—Cl1113.22 (3)
C10—C9—C8119.4 (2)
N1—C1—C2—C50.5 (4)C8—C7—O1—Zn125.3 (2)
C6—C1—C2—C5179.5 (2)C1—C6—O1—C7−178.79 (18)
N1—C3—C4—C50.0 (4)C1—C6—O1—Zn1−34.2 (2)
C3—C4—C5—C20.7 (4)C8—N2—Zn1—N140.8 (2)
C1—C2—C5—C4−0.9 (4)C12—N2—Zn1—N1−148.24 (15)
N1—C1—C6—O120.9 (3)C8—N2—Zn1—O116.36 (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—C9169.19 (19)C12—N2—Zn1—Cl285.04 (16)
N2—C8—C9—C10−0.5 (3)C8—N2—Zn1—Cl1157.83 (14)
C7—C8—C9—C10178.7 (2)C12—N2—Zn1—Cl1−31.21 (16)
C8—C9—C10—C110.9 (3)C1—N1—Zn1—N2−40.5 (2)
C9—C10—C11—C12−0.6 (3)C3—N1—Zn1—N2140.93 (17)
C10—C11—C12—N2−0.1 (4)C1—N1—Zn1—O1−16.06 (16)
C2—C1—N1—C30.2 (3)C3—N1—Zn1—O1165.40 (19)
C6—C1—N1—C3−178.8 (2)C1—N1—Zn1—Cl285.67 (16)
C2—C1—N1—Zn1−178.39 (17)C3—N1—Zn1—Cl2−92.87 (18)
C6—C1—N1—Zn12.6 (3)C1—N1—Zn1—Cl1−157.66 (16)
C4—C3—N1—C1−0.5 (4)C3—N1—Zn1—Cl123.80 (18)
C4—C3—N1—Zn1178.1 (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—N1173.15 (17)
C9—C8—N2—Zn1171.03 (15)C6—O1—Zn1—N128.48 (15)
C7—C8—N2—Zn1−8.2 (2)C7—O1—Zn1—Cl274.03 (16)
C11—C12—N2—C80.5 (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—C6169.28 (19)C6—O1—Zn1—Cl1109.91 (15)
Table 1
Selected geometric parameters (Å) top
Cl1—Zn12.2803 (6)N2—Zn12.1128 (18)
Cl2—Zn12.2642 (7)O1—Zn12.2252 (16)
N1—Zn12.1178 (18)
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Li, J. M. (2007). Acta Cryst. E63, m2241.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Li, J. M. (2008). Acta Cryst. E64, m1467.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.