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Acta Cryst. (2008). E64, m1320    [ doi:10.1107/S1600536808030225 ]

Diiodidobis(1-methylimidazole-[kappa]N3)cadmium(II)

J. Zhao

Abstract top

In the title compound, [CdI2(C4H6N2)2], each Cd atom is coordinated by two N atoms from two 1-methylimidazole and two iodido ligands. The Cd atom has a distorted tetrahedral coordination. Intermolecular C-H...I hydrogen bonds link the monomeric units, generating a one-dimensional supramolecular chain along the a axis.

Comment top

In the title compound (I) (Fig. 1), each Cd atom is tetrahedrally surrounded showing a CdN2Cl2 coordination sphere. Each Mim(Mim = N-methylimidazole) acts as a monodentate-N(imidazole) donor ligand. The two imidazole rings are planar and make a dihedral angle of 69.46 (3)°. The Cd—N(imidazole) distance [Cd—N2, 2.238 (9); Cd—N4, 2.201 (10)°] is comparable with reported data (Chand, et al., 2003). The Cd—I bond distances are 2.7248 (13)Å and 2.7358 (13)Å. The angles extended in tetrahedral CdN2I2 geometry are I1—Cd—I2 119.20 (5)°, N4—Cd—N2, 112.2 (4)° and suggest a small distortion. All other angles are within the limits of distorted Td-geometry. Intermolecular C—H···I hydrogen bonds link the monomeric units to produce a one-dimensional supramolecular chain along the a-axis.

In the corresponding copper compound [Cd(HaaiMe)2Cl2] (Chand, et al., 2003), the CdII has a distorted tetrahedron coordination environment.

Related literature top

For a related structure, see: Chand et al. (2003).

Experimental top

N-Methylimidazole (32.8 mg, 0.4 mmol) in MeOH (10 ml) was added in dropwise to a stirred methanolic solution (10 ml) of CdI2 (366.2 mg, 0.1 mmol) at room temperature (298 K). The colorless solution was left undisturbed for 2 weeks. Colorless crystals were obtained. These were then washed with water and finally, dried in vacuo.

Refinement top

H atoms were positioned geometrically (C—H = 0.93Å or 0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 or 1.5 times Ueq(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: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing of (I), viewed down the b-axis.
Diiodidobis(1-methylimidazole-κN3)cadmium(II) top
Crystal data top
[CdI2(C4H6N2)2]F(000) = 1936
Mr = 530.43Dx = 2.386 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 13.5570 (9) Åθ = 10–14°
b = 14.5615 (14) ŵ = 5.64 mm−1
c = 14.9585 (19) ÅT = 298 K
V = 2953.0 (5) Å3Block, colorless
Z = 80.10 × 0.10 × 0.10 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2768 independent reflections
Radiation source: fine-focus sealed tube1811 reflections with I > 2σ(I)
graphiteRint = 0.013
Thin–slice ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = 0→16
Tmin = 0.574, Tmax = 0.579k = 0→17
2888 measured reflectionsl = 0→18
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)] = 0.063H-atom parameters constrained
wR(F2) = 0.178 w = 1/[σ2(Fo2) + (0.1P)2 + 1P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
2768 reflectionsΔρmax = 1.18 e Å−3
137 parametersΔρmin = −0.85 e Å−3
40 restraintsExtinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0017 (2)
Crystal data top
[CdI2(C4H6N2)2]V = 2953.0 (5) Å3
Mr = 530.43Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.5570 (9) ŵ = 5.64 mm−1
b = 14.5615 (14) ÅT = 298 K
c = 14.9585 (19) Å0.10 × 0.10 × 0.10 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2768 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1811 reflections with I > 2σ(I)
Tmin = 0.574, Tmax = 0.579Rint = 0.013
2888 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.178Δρmax = 1.18 e Å−3
S = 0.99Δρmin = −0.85 e Å−3
2768 reflectionsAbsolute structure: ?
137 parametersFlack parameter: ?
40 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
Cd1.20251 (6)0.53829 (6)1.04405 (6)0.0520 (3)
I11.21055 (7)0.59157 (7)0.86882 (6)0.0621 (3)
C11.5970 (10)0.6525 (10)1.0696 (12)0.080 (5)
H1A1.57980.70041.02840.120*
H1B1.64750.61461.04390.120*
H1C1.62080.67921.12420.120*
N11.5119 (6)0.5977 (7)1.0881 (7)0.052 (3)
I21.13534 (7)0.36699 (7)1.08491 (8)0.0707 (4)
N21.3612 (7)0.5502 (7)1.0836 (7)0.052 (3)
C21.5085 (12)0.5226 (11)1.1438 (10)0.070 (4)
H2A1.56020.49541.17500.084*
N30.9637 (7)0.6773 (6)1.1774 (6)0.047 (2)
C31.4143 (12)0.4979 (10)1.1428 (10)0.072 (4)
H3A1.38770.45121.17780.087*
N41.1068 (8)0.6296 (7)1.1229 (7)0.052 (2)
C41.4208 (9)0.6106 (9)1.0530 (9)0.054 (3)
H4A1.40400.65661.01260.065*
C50.8536 (8)0.6817 (10)1.2037 (9)0.061 (4)
H5A0.82040.62801.18190.092*
H5B0.82420.73551.17790.092*
H5C0.84790.68441.26760.092*
C61.0338 (10)0.7448 (10)1.1951 (9)0.066 (3)
H6A1.02300.80051.22380.080*
C71.1210 (11)0.7135 (11)1.1622 (11)0.078 (4)
H7A1.18100.74431.16580.093*
C81.0131 (9)0.6115 (9)1.1374 (8)0.054 (3)
H8A0.98410.55631.12060.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd0.0379 (5)0.0590 (5)0.0591 (6)0.0005 (4)0.0060 (4)0.0008 (5)
I10.0644 (6)0.0656 (6)0.0564 (5)−0.0062 (4)−0.0039 (4)0.0073 (4)
C10.046 (8)0.069 (9)0.125 (14)−0.023 (7)−0.017 (8)−0.024 (9)
N10.024 (5)0.064 (6)0.068 (7)−0.011 (4)0.009 (5)−0.022 (6)
I20.0632 (6)0.0605 (6)0.0883 (8)−0.0060 (4)0.0029 (5)0.0166 (5)
N20.037 (5)0.052 (6)0.067 (7)0.003 (5)−0.008 (5)−0.009 (5)
C20.068 (10)0.081 (11)0.062 (9)0.013 (8)−0.010 (8)−0.012 (8)
N30.041 (4)0.050 (5)0.049 (5)0.002 (4)0.001 (4)−0.001 (4)
C30.081 (11)0.064 (8)0.073 (10)0.027 (8)0.003 (8)0.016 (8)
N40.052 (5)0.056 (5)0.050 (5)0.000 (4)0.003 (4)0.002 (4)
C40.038 (6)0.065 (8)0.059 (8)−0.022 (6)0.010 (6)0.006 (6)
C50.040 (7)0.076 (9)0.068 (9)0.014 (6)−0.001 (6)0.009 (7)
C60.060 (6)0.056 (5)0.083 (8)−0.001 (5)−0.007 (6)−0.013 (5)
C70.069 (6)0.071 (6)0.094 (8)−0.022 (5)0.015 (6)−0.009 (6)
C80.052 (5)0.055 (5)0.054 (6)0.002 (4)0.007 (5)−0.010 (5)
Geometric parameters (Å, °) top
Cd—N42.201 (10)N3—C81.313 (14)
Cd—N22.238 (9)N3—C61.392 (16)
Cd—I22.7248 (13)N3—C51.544 (14)
Cd—I12.7358 (13)C3—H3A0.9300
C1—N11.429 (16)N4—C81.315 (16)
C1—H1A0.9600N4—C71.369 (18)
C1—H1B0.9600C4—H4A0.9300
C1—H1C0.9600C5—H5A0.9600
N1—C41.355 (16)C5—H5B0.9600
N1—C21.377 (19)C5—H5C0.9600
N2—C41.279 (15)C6—C71.360 (18)
N2—C31.372 (16)C6—H6A0.9300
C2—C31.33 (2)C7—H7A0.9300
C2—H2A0.9300C8—H8A0.9300
N4—Cd—N2112.2 (4)C2—C3—N2111.2 (14)
N4—Cd—I2103.7 (3)C2—C3—H3A124.4
N2—Cd—I2109.4 (3)N2—C3—H3A124.4
N4—Cd—I1111.4 (3)C8—N4—C7104.1 (11)
N2—Cd—I1101.1 (3)C8—N4—Cd122.5 (9)
I2—Cd—I1119.20 (5)C7—N4—Cd133.3 (9)
N1—C1—H1A109.5N2—C4—N1110.0 (12)
N1—C1—H1B109.5N2—C4—H4A125.0
H1A—C1—H1B109.5N1—C4—H4A125.0
N1—C1—H1C109.5N3—C5—H5A109.5
H1A—C1—H1C109.5N3—C5—H5B109.5
H1B—C1—H1C109.5H5A—C5—H5B109.5
C4—N1—C2108.3 (10)N3—C5—H5C109.5
C4—N1—C1125.7 (12)H5A—C5—H5C109.5
C2—N1—C1126.0 (12)H5B—C5—H5C109.5
C4—N2—C3106.3 (12)C7—C6—N3106.8 (12)
C4—N2—Cd124.4 (9)C7—C6—H6A126.6
C3—N2—Cd129.2 (10)N3—C6—H6A126.6
C3—C2—N1103.9 (13)C6—C7—N4109.3 (12)
C3—C2—H2A128.0C6—C7—H7A125.3
N1—C2—H2A128.0N4—C7—H7A125.3
C8—N3—C6104.7 (10)N3—C8—N4114.9 (12)
C8—N3—C5129.7 (10)N3—C8—H8A122.5
C6—N3—C5125.6 (10)N4—C8—H8A122.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···I1i0.963.033.9797169
Symmetry codes: (i) x−1/2, −y+3/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···I1i0.963.033.9797169
Symmetry codes: (i) x−1/2, −y+3/2, −z+2.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (Y2006B12).

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Chand, B. G., Ray, U. S., Mostafa, G. M., Lu, T., Falvello, L. R., Soler, T., Tomàs, M. & Sinha, C. (2003). Polyhedron, 22, 3161–3169.

Sheldrick, G. M. (2004). SADABS. University of Go''ttingen, Germany.

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