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Acta Cryst. (2007). E63, m2501-m2502    [ doi:10.1107/S1600536807043255 ]

Dichlorido{2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine-[kappa]3N,N',N''}cadmium(II) acetonitrile solvate

R.-Q. Fan, P. Wang, Y.-L. Yang and Z.-W. Lv

Abstract top

In the title compound, [Cd(C27H31N3)Cl2]·CH3CN, the coordination geometry around the five-coordinated CdII atom can be described as distorted trigonal-bipyramidal, formed by two Cl atoms, one pyridine N and two imine N atoms from the bis(iminoalkyl)pyridine ligand. The dihedral angles between the substituted phenyl rings and the plane formed by the three coordinated N atoms are 90.6 (1) and 86.0 (1)°. C-H...Cl hydrogen bonds link the molecules into a three-dimensional supramolecular network.

Comment top

Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential applications in the areas of sensor technologies and electro-luminescent devices (Tang & Vanslyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we have reported a series of cadmium complexes derived from bis(iminoalkyl)pyridine ligands (Fan et al., 2004). We report here the crystal structure of the title compound, a new cadmium complex with 2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine ligand.

As shown in Fig. 1, the asymmetric unit of the title compound contains one independent complex molecule and a solvated acetonitrile molecule. The central CdII atom is five-coordinated in a distorted trigonal-bipyramidal geometry, defined by two Cl atoms, one pyridine N and two imine N atoms from the bis(iminoalkyl)pyridine ligand. The Cd—N bond lengths [2.306 (3)–2.416 (3) Å] (Table 1) fall into the range of observed values in the similar cadmium complexes (Fan et al., 2004). The dihedral angles between the substituted phenyl rings and the plane formed by three coordinated N atoms are 90.6 (1)° and 86.0 (1)°, respectively.

In the crystal structure, weak intermolecular C—H···Cl hydrogen bonds (Table 2) play an important role to link the molecules into a three-dimensional supramolecular network (Fig.2).

Related literature top

For related literature, see: Fan et al. (2004); Tang & Vanslyke (1987); Wang (2001).

Experimental top

The title complex was synthesized according to the literature procedure (Fan et al., 2004). To a solution of 2,6-diacetylpyridine (2.4 g, 14.7 mmol) in absolute methanol (50 ml) was added 2,4,6-trimethylaniline (6.2 ml, 44.1 mmol). After the addition of several drops of formic acid, the reaction mixture was refluxed for 24 h and then allowed to cool down to room temperature. The crude product precipitated as yellow powder. Pure 2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine was obtained in 83% yield (4.8 g). A mixture of this ligand (0.30 g, 0.75 mmol) and CdCl2·2.5H2O (0.17 g, 0.75 mmol) in acetonitrile was stirred at room temperature for 12 h. Evaporation of the solvent gave the crude product as a yellowish powder. Yellowish needle crystals suitable for X-ray diffraction were obtained upon recrystallization from acetonitrile/dichloromethane (2:1 v/v) (yield 84%, 0.39 g).

Refinement top

H atoms were positioned geometrically and refined as riding, with C—H = 0.93Å (CH) and Uiso(H) = 1.2Ueq(C), and with C—H = 0.96Å (CH3) and Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound along the b axis. Hydrogen bonds are indicated by dashed lines.
Dichlorido{2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl] pyridine-κ3 N,N',N''}cadmium(II) acetonitrile solvate top
Crystal data top
[Cd(C27H31N3)Cl2]·C2H3NF000 = 1272
Mr = 621.90Dx = 1.372 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6108 reflections
a = 14.545 (3) Åθ = 1.7–26.1º
b = 15.074 (3) ŵ = 0.93 mm−1
c = 14.758 (3) ÅT = 295 (2) K
β = 111.516 (2)ºNeedle, yellow
V = 3010.3 (11) Å30.42 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5948 independent reflections
Radiation source: fine-focus sealed tube4046 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.086
T = 295(2) Kθmax = 26.1º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.697, Tmax = 0.851k = −16→18
16698 measured reflectionsl = −18→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.091  w = 1/[σ2(Fo2) + (0.0303P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.009
5948 reflectionsΔρmax = 0.69 e Å−3
334 parametersΔρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cd(C27H31N3)Cl2]·C2H3NV = 3010.3 (11) Å3
Mr = 621.90Z = 4
Monoclinic, P21/nMo Kα
a = 14.545 (3) ŵ = 0.93 mm−1
b = 15.074 (3) ÅT = 295 (2) K
c = 14.758 (3) Å0.42 × 0.20 × 0.18 mm
β = 111.516 (2)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5948 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4046 reflections with I > 2σ(I)
Tmin = 0.697, Tmax = 0.851Rint = 0.086
16698 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042334 parameters
wR(F2) = 0.091H-atom parameters constrained
S = 0.88Δρmax = 0.69 e Å−3
5948 reflectionsΔρmin = −0.39 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.749428 (18)0.180077 (17)0.306446 (18)0.04833 (11)
Cl10.57035 (7)0.16398 (7)0.23566 (9)0.0755 (3)
Cl20.84039 (7)0.04834 (7)0.29937 (8)0.0713 (3)
N10.76671 (19)0.18576 (18)0.4751 (2)0.0456 (7)
N20.81540 (19)0.31434 (18)0.3745 (2)0.0466 (7)
N30.7892 (2)0.2711 (2)0.1911 (2)0.0529 (7)
N40.6107 (4)0.4175 (3)0.5283 (5)0.1161 (18)
C10.7983 (2)0.2586 (2)0.5210 (2)0.0468 (9)
C20.8220 (2)0.3328 (2)0.4650 (3)0.0475 (9)
C30.8523 (3)0.4155 (3)0.5056 (3)0.0644 (11)
H30.85800.42780.56920.077*
C40.8738 (3)0.4796 (3)0.4492 (3)0.0695 (12)
H40.89110.53660.47360.083*
C50.8697 (3)0.4589 (2)0.3582 (3)0.0645 (11)
H50.88780.50060.32140.077*
C60.8381 (2)0.3750 (2)0.3204 (3)0.0508 (9)
C70.8266 (3)0.3479 (3)0.2199 (3)0.0547 (10)
C80.8127 (3)0.2753 (3)0.6248 (3)0.0652 (11)
H8A0.79820.22210.65290.098*
H8B0.76920.32190.62840.098*
H8C0.88000.29240.66010.098*
C90.8587 (3)0.4115 (3)0.1586 (3)0.0799 (13)
H9A0.85440.38290.09910.120*
H9B0.92580.42940.19370.120*
H9C0.81660.46270.14400.120*
C100.7476 (2)0.1111 (2)0.5263 (2)0.0453 (8)
C110.8242 (3)0.0495 (3)0.5670 (3)0.0547 (10)
C120.8031 (3)−0.0242 (3)0.6125 (3)0.0657 (11)
H120.8530−0.06550.64070.079*
C130.7121 (3)−0.0390 (3)0.6178 (3)0.0653 (11)
C140.6400 (3)0.0233 (3)0.5782 (3)0.0611 (10)
H140.57830.01460.58240.073*
C150.6555 (3)0.0993 (2)0.5317 (3)0.0525 (9)
C160.9252 (3)0.0656 (3)0.5663 (3)0.0762 (13)
H16A0.96590.01460.59200.114*
H16B0.95370.11650.60570.114*
H16C0.92080.07610.50070.114*
C170.6943 (4)−0.1210 (3)0.6687 (4)0.1025 (17)
H17A0.6443−0.10870.69490.154*
H17B0.7545−0.13740.72060.154*
H17C0.6730−0.16890.62280.154*
C180.5753 (3)0.1681 (3)0.4925 (3)0.0726 (12)
H18A0.59610.22250.52780.109*
H18B0.51600.14740.49980.109*
H18C0.56280.17810.42470.109*
C190.7759 (3)0.2367 (2)0.0965 (3)0.0545 (9)
C200.6847 (3)0.2440 (3)0.0224 (3)0.0680 (11)
C210.6716 (4)0.2024 (3)−0.0655 (3)0.0825 (14)
H210.61040.2065−0.11600.099*
C220.7456 (5)0.1553 (3)−0.0807 (4)0.0856 (15)
C230.8366 (4)0.1519 (3)−0.0054 (4)0.0835 (14)
H230.88800.1216−0.01500.100*
C240.8540 (3)0.1918 (3)0.0835 (3)0.0681 (11)
C250.6026 (3)0.2975 (3)0.0350 (3)0.0898 (15)
H25A0.58230.27000.08330.135*
H25B0.54750.3000−0.02580.135*
H25C0.62560.35650.05550.135*
C260.7284 (5)0.1099 (4)−0.1777 (4)0.132 (2)
H26A0.66750.0772−0.19760.198*
H26B0.78200.0701−0.17070.198*
H26C0.72470.1539−0.22600.198*
C270.9545 (3)0.1863 (3)0.1635 (4)0.0876 (15)
H27A0.99810.15250.14120.131*
H27B0.94880.15780.21940.131*
H27C0.98070.24490.18080.131*
C280.5801 (5)0.4177 (4)0.4466 (6)0.098 (2)
C290.5408 (5)0.4164 (5)0.3409 (5)0.156 (3)
H29A0.52940.35610.31850.234*
H29B0.58740.44340.31720.234*
H29C0.47970.44870.31710.234*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.05459 (18)0.04431 (16)0.04645 (17)0.00312 (13)0.01896 (13)−0.00318 (12)
Cl10.0547 (6)0.0804 (8)0.0827 (8)0.0069 (5)0.0148 (5)−0.0143 (6)
Cl20.0732 (7)0.0640 (7)0.0751 (8)0.0229 (5)0.0252 (6)−0.0017 (5)
N10.0445 (16)0.0469 (17)0.0471 (18)0.0001 (14)0.0189 (14)−0.0005 (14)
N20.0485 (17)0.0431 (16)0.0477 (19)−0.0003 (14)0.0169 (14)−0.0012 (14)
N30.0654 (19)0.053 (2)0.0445 (19)0.0105 (16)0.0254 (15)0.0009 (14)
N40.109 (4)0.097 (4)0.147 (5)−0.001 (3)0.052 (4)0.015 (4)
C10.043 (2)0.059 (2)0.038 (2)0.0008 (17)0.0146 (16)−0.0017 (17)
C20.046 (2)0.050 (2)0.044 (2)−0.0054 (16)0.0139 (17)−0.0056 (17)
C30.078 (3)0.061 (3)0.054 (3)−0.013 (2)0.025 (2)−0.014 (2)
C40.087 (3)0.050 (2)0.067 (3)−0.016 (2)0.023 (2)−0.011 (2)
C50.079 (3)0.046 (2)0.070 (3)−0.007 (2)0.028 (2)0.006 (2)
C60.055 (2)0.048 (2)0.052 (2)0.0065 (18)0.0226 (19)0.0077 (18)
C70.059 (2)0.052 (2)0.057 (3)0.0104 (19)0.026 (2)0.0110 (18)
C80.071 (3)0.078 (3)0.048 (2)−0.013 (2)0.023 (2)−0.008 (2)
C90.120 (4)0.062 (3)0.073 (3)−0.008 (3)0.053 (3)0.010 (2)
C100.050 (2)0.049 (2)0.038 (2)−0.0051 (17)0.0179 (17)−0.0026 (15)
C110.061 (2)0.063 (3)0.041 (2)0.005 (2)0.0196 (19)0.0036 (18)
C120.085 (3)0.062 (3)0.046 (3)0.014 (2)0.019 (2)0.0099 (19)
C130.086 (3)0.065 (3)0.048 (3)−0.011 (2)0.028 (2)0.002 (2)
C140.072 (3)0.067 (3)0.054 (3)−0.017 (2)0.034 (2)−0.008 (2)
C150.056 (2)0.052 (2)0.054 (2)−0.0070 (19)0.0249 (19)−0.0075 (18)
C160.063 (3)0.098 (4)0.067 (3)0.018 (2)0.024 (2)0.019 (2)
C170.134 (4)0.084 (4)0.095 (4)−0.012 (3)0.049 (3)0.033 (3)
C180.060 (3)0.073 (3)0.094 (4)0.001 (2)0.040 (2)−0.003 (2)
C190.072 (3)0.056 (2)0.043 (2)0.011 (2)0.031 (2)0.0057 (18)
C200.087 (3)0.064 (3)0.054 (3)0.013 (2)0.027 (2)0.006 (2)
C210.109 (4)0.082 (3)0.046 (3)0.004 (3)0.016 (3)0.008 (2)
C220.139 (5)0.069 (3)0.061 (3)0.011 (3)0.051 (3)−0.003 (2)
C230.123 (4)0.072 (3)0.079 (4)0.026 (3)0.065 (3)0.008 (3)
C240.094 (3)0.061 (3)0.062 (3)0.016 (2)0.044 (3)0.011 (2)
C250.094 (3)0.106 (4)0.065 (3)0.036 (3)0.024 (3)0.011 (3)
C260.222 (7)0.123 (5)0.065 (4)0.012 (4)0.069 (4)−0.024 (3)
C270.077 (3)0.102 (4)0.096 (4)0.025 (3)0.047 (3)0.019 (3)
C280.093 (4)0.072 (3)0.144 (6)0.005 (3)0.060 (5)0.023 (4)
C290.188 (7)0.158 (7)0.131 (7)−0.002 (5)0.069 (5)0.037 (5)
Geometric parameters (Å, °) top
Cd1—N22.306 (3)C14—C151.396 (5)
Cd1—N12.410 (3)C14—H140.9300
Cd1—Cl22.4097 (10)C15—C181.507 (5)
Cd1—N32.416 (3)C16—H16A0.9600
Cd1—Cl12.4369 (11)C16—H16B0.9600
N1—C11.284 (4)C16—H16C0.9600
N1—C101.438 (4)C17—H17A0.9600
N2—C61.332 (4)C17—H17B0.9600
N2—C21.332 (4)C17—H17C0.9600
N3—C71.284 (4)C18—H18A0.9600
N3—C191.434 (4)C18—H18B0.9600
N4—C281.123 (7)C18—H18C0.9600
C1—C81.490 (5)C19—C201.380 (5)
C1—C21.504 (5)C19—C241.395 (5)
C2—C31.385 (5)C20—C211.390 (6)
C3—C41.383 (5)C20—C251.507 (5)
C3—H30.9300C21—C221.374 (6)
C4—C51.358 (5)C21—H210.9300
C4—H40.9300C22—C231.383 (6)
C5—C61.391 (5)C22—C261.523 (6)
C5—H50.9300C23—C241.380 (6)
C6—C71.488 (5)C23—H230.9300
C7—C91.505 (5)C24—C271.507 (6)
C8—H8A0.9600C25—H25A0.9600
C8—H8B0.9600C25—H25B0.9600
C8—H8C0.9600C25—H25C0.9600
C9—H9A0.9600C26—H26A0.9600
C9—H9B0.9600C26—H26B0.9600
C9—H9C0.9600C26—H26C0.9600
C10—C151.382 (4)C27—H27A0.9600
C10—C111.405 (5)C27—H27B0.9600
C11—C121.389 (5)C27—H27C0.9600
C11—C161.493 (5)C28—C291.451 (8)
C12—C131.373 (5)C29—H29A0.9600
C12—H120.9300C29—H29B0.9600
C13—C141.369 (5)C29—H29C0.9600
C13—C171.517 (5)
N2—Cd1—N169.50 (10)C15—C14—H14118.8
N2—Cd1—Cl2126.50 (7)C10—C15—C14117.9 (4)
N1—Cd1—Cl2102.89 (7)C10—C15—C18121.2 (3)
N2—Cd1—N368.88 (10)C14—C15—C18120.8 (3)
N1—Cd1—N3138.28 (10)C11—C16—H16A109.5
Cl2—Cd1—N399.21 (7)C11—C16—H16B109.5
N2—Cd1—Cl1118.86 (7)H16A—C16—H16B109.5
N1—Cd1—Cl197.85 (7)C11—C16—H16C109.5
Cl2—Cd1—Cl1114.64 (4)H16A—C16—H16C109.5
N3—Cd1—Cl1104.43 (7)H16B—C16—H16C109.5
C1—N1—C10119.5 (3)C13—C17—H17A109.5
C1—N1—Cd1117.2 (2)C13—C17—H17B109.5
C10—N1—Cd1123.2 (2)H17A—C17—H17B109.5
C6—N2—C2121.0 (3)C13—C17—H17C109.5
C6—N2—Cd1119.8 (2)H17A—C17—H17C109.5
C2—N2—Cd1119.0 (2)H17B—C17—H17C109.5
C7—N3—C19122.6 (3)C15—C18—H18A109.5
C7—N3—Cd1117.4 (2)C15—C18—H18B109.5
C19—N3—Cd1120.0 (2)H18A—C18—H18B109.5
N1—C1—C8125.1 (3)C15—C18—H18C109.5
N1—C1—C2117.1 (3)H18A—C18—H18C109.5
C8—C1—C2117.8 (3)H18B—C18—H18C109.5
N2—C2—C3121.1 (3)C20—C19—C24121.7 (4)
N2—C2—C1116.7 (3)C20—C19—N3119.3 (3)
C3—C2—C1122.1 (3)C24—C19—N3118.9 (3)
C4—C3—C2118.3 (4)C19—C20—C21117.8 (4)
C4—C3—H3120.8C19—C20—C25121.3 (4)
C2—C3—H3120.8C21—C20—C25120.9 (4)
C5—C4—C3119.8 (4)C22—C21—C20122.5 (4)
C5—C4—H4120.1C22—C21—H21118.7
C3—C4—H4120.1C20—C21—H21118.7
C4—C5—C6119.5 (4)C21—C22—C23117.7 (4)
C4—C5—H5120.2C21—C22—C26121.1 (5)
C6—C5—H5120.2C23—C22—C26121.2 (5)
N2—C6—C5120.1 (4)C24—C23—C22122.3 (4)
N2—C6—C7116.6 (3)C24—C23—H23118.8
C5—C6—C7123.3 (3)C22—C23—H23118.8
N3—C7—C6117.2 (3)C23—C24—C19117.9 (4)
N3—C7—C9124.2 (4)C23—C24—C27120.5 (4)
C6—C7—C9118.6 (4)C19—C24—C27121.6 (4)
C1—C8—H8A109.5C20—C25—H25A109.5
C1—C8—H8B109.5C20—C25—H25B109.5
H8A—C8—H8B109.5H25A—C25—H25B109.5
C1—C8—H8C109.5C20—C25—H25C109.5
H8A—C8—H8C109.5H25A—C25—H25C109.5
H8B—C8—H8C109.5H25B—C25—H25C109.5
C7—C9—H9A109.5C22—C26—H26A109.5
C7—C9—H9B109.5C22—C26—H26B109.5
H9A—C9—H9B109.5H26A—C26—H26B109.5
C7—C9—H9C109.5C22—C26—H26C109.5
H9A—C9—H9C109.5H26A—C26—H26C109.5
H9B—C9—H9C109.5H26B—C26—H26C109.5
C15—C10—C11121.6 (3)C24—C27—H27A109.5
C15—C10—N1120.6 (3)C24—C27—H27B109.5
C11—C10—N1117.8 (3)H27A—C27—H27B109.5
C12—C11—C10117.1 (3)C24—C27—H27C109.5
C12—C11—C16121.7 (4)H27A—C27—H27C109.5
C10—C11—C16121.2 (3)H27B—C27—H27C109.5
C13—C12—C11123.0 (4)N4—C28—C29179.0 (7)
C13—C12—H12118.5C28—C29—H29A109.5
C11—C12—H12118.5C28—C29—H29B109.5
C14—C13—C12117.9 (4)H29A—C29—H29B109.5
C14—C13—C17121.9 (4)C28—C29—H29C109.5
C12—C13—C17120.2 (4)H29A—C29—H29C109.5
C13—C14—C15122.5 (4)H29B—C29—H29C109.5
C13—C14—H14118.8
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···Cl1i0.962.663.614 (4)172
C16—H16A···Cl2ii0.962.843.681 (4)146
C16—H16C···Cl20.962.803.680 (4)153
C29—H29B···Cl2iii0.962.813.721 (6)159
C5—H5···Cl1iii0.932.743.622 (4)158
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Cd1—N22.306 (3)Cd1—N32.416 (3)
Cd1—N12.410 (3)Cd1—Cl12.4369 (11)
Cd1—Cl22.4097 (10)
N2—Cd1—N169.50 (10)Cl2—Cd1—N399.21 (7)
N2—Cd1—Cl2126.50 (7)N2—Cd1—Cl1118.86 (7)
N1—Cd1—Cl2102.89 (7)N1—Cd1—Cl197.85 (7)
N2—Cd1—N368.88 (10)Cl2—Cd1—Cl1114.64 (4)
N1—Cd1—N3138.28 (10)N3—Cd1—Cl1104.43 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···Cl1i0.962.663.614 (4)172
C16—H16A···Cl2ii0.962.843.681 (4)146
C16—H16C···Cl20.962.803.680 (4)153
C29—H29B···Cl2iii0.962.813.721 (6)159
C5—H5···Cl1iii0.932.743.622 (4)158
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.
Acknowledgements top

This work was supported by the Development Program for Outstanding Young Teachers in Harbin Institute of Technology (HITQNJS.2006.029), the Science Innovation Special Foundation of Harbin City in China (2006RFQXG037), the Young Foundation of Heilongjiang Province in China (QC06C029), and the National Natural Science Foundation of China (20671025).

references
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