Diiodidobis(1-methyl­imidazole-κN3)cadmium(II)

Zhao, J.

doi:10.1107/S1600536808030225

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1320

doi:10.1107/S1600536808030225

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Diiodidobis(1-methylimidazole-κN³)cadmium(II)

Juan Zhao ^a ^*

^aCollege of Mechanical Engineering, Qingdao Technological University, Qingdao 266033, People's Republic of China
^*Correspondence e-mail: zhaojuanqd@163.com

(Received 13 September 2008; accepted 19 September 2008; online 24 September 2008)

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.

Related literature

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

Experimental

Crystal data

[CdI₂(C₄H₆N₂)₂]
M_r = 530.43
Orthorhombic, P b c a
a = 13.5570 (9) Å
b = 14.5615 (14) Å
c = 14.9585 (19) Å
V = 2953.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.64 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.574, T_max = 0.579
2888 measured reflections
2768 independent reflections
1811 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.178
S = 0.98
2768 reflections
137 parameters
40 restraints
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯I1ⁱ	0.96	3.03	3.9797	169
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030225/bq2097sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030225/bq2097Isup2.hkl

checkCIF report

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 Cd^II 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.

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

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	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
M_r = 530.43	D_x = 2.386 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 13.5570 (9) Å	θ = 10–14°
b = 14.5615 (14) Å	µ = 5.64 mm⁻¹
c = 14.9585 (19) Å	T = 298 K
V = 2953.0 (5) Å³	Block, colorless
Z = 8	0.10 × 0.10 × 0.10 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2768 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Thin–slice ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = 0→16
T_min = 0.574, T_max = 0.579	k = 0→17
2888 measured reflections	l = 0→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.1P)² + 1P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
2768 reflections	Δρ_max = 1.18 e Å⁻³
137 parameters	Δρ_min = −0.85 e Å⁻³
40 restraints	Extinction correction: SHELXTL (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (2)

Crystal data top

[CdI₂(C₄H₆N₂)₂]	V = 2953.0 (5) Å³
M_r = 530.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.5570 (9) Å	µ = 5.64 mm⁻¹
b = 14.5615 (14) Å	T = 298 K
c = 14.9585 (19) Å	0.10 × 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)
T_min = 0.574, T_max = 0.579	R_int = 0.013
2888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	40 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 0.99	Δρ_max = 1.18 e Å⁻³
2768 reflections	Δρ_min = −0.85 e Å⁻³
137 parameters

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

	x	y	z	U_iso*/U_eq
Cd	1.20251 (6)	0.53829 (6)	1.04405 (6)	0.0520 (3)
I1	1.21055 (7)	0.59157 (7)	0.86882 (6)	0.0621 (3)
C1	1.5970 (10)	0.6525 (10)	1.0696 (12)	0.080 (5)
H1A	1.5798	0.7004	1.0284	0.120*
H1B	1.6475	0.6146	1.0439	0.120*
H1C	1.6208	0.6792	1.1242	0.120*
N1	1.5119 (6)	0.5977 (7)	1.0881 (7)	0.052 (3)
I2	1.13534 (7)	0.36699 (7)	1.08491 (8)	0.0707 (4)
N2	1.3612 (7)	0.5502 (7)	1.0836 (7)	0.052 (3)
C2	1.5085 (12)	0.5226 (11)	1.1438 (10)	0.070 (4)
H2A	1.5602	0.4954	1.1750	0.084*
N3	0.9637 (7)	0.6773 (6)	1.1774 (6)	0.047 (2)
C3	1.4143 (12)	0.4979 (10)	1.1428 (10)	0.072 (4)
H3A	1.3877	0.4512	1.1778	0.087*
N4	1.1068 (8)	0.6296 (7)	1.1229 (7)	0.052 (2)
C4	1.4208 (9)	0.6106 (9)	1.0530 (9)	0.054 (3)
H4A	1.4040	0.6566	1.0126	0.065*
C5	0.8536 (8)	0.6817 (10)	1.2037 (9)	0.061 (4)
H5A	0.8204	0.6280	1.1819	0.092*
H5B	0.8242	0.7355	1.1779	0.092*
H5C	0.8479	0.6844	1.2676	0.092*
C6	1.0338 (10)	0.7448 (10)	1.1951 (9)	0.066 (3)
H6A	1.0230	0.8005	1.2238	0.080*
C7	1.1210 (11)	0.7135 (11)	1.1622 (11)	0.078 (4)
H7A	1.1810	0.7443	1.1658	0.093*
C8	1.0131 (9)	0.6115 (9)	1.1374 (8)	0.054 (3)
H8A	0.9841	0.5563	1.1206	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.0379 (5)	0.0590 (5)	0.0591 (6)	0.0005 (4)	0.0060 (4)	0.0008 (5)
I1	0.0644 (6)	0.0656 (6)	0.0564 (5)	−0.0062 (4)	−0.0039 (4)	0.0073 (4)
C1	0.046 (8)	0.069 (9)	0.125 (14)	−0.023 (7)	−0.017 (8)	−0.024 (9)
N1	0.024 (5)	0.064 (6)	0.068 (7)	−0.011 (4)	0.009 (5)	−0.022 (6)
I2	0.0632 (6)	0.0605 (6)	0.0883 (8)	−0.0060 (4)	0.0029 (5)	0.0166 (5)
N2	0.037 (5)	0.052 (6)	0.067 (7)	0.003 (5)	−0.008 (5)	−0.009 (5)
C2	0.068 (10)	0.081 (11)	0.062 (9)	0.013 (8)	−0.010 (8)	−0.012 (8)
N3	0.041 (4)	0.050 (5)	0.049 (5)	0.002 (4)	0.001 (4)	−0.001 (4)
C3	0.081 (11)	0.064 (8)	0.073 (10)	0.027 (8)	0.003 (8)	0.016 (8)
N4	0.052 (5)	0.056 (5)	0.050 (5)	0.000 (4)	0.003 (4)	0.002 (4)
C4	0.038 (6)	0.065 (8)	0.059 (8)	−0.022 (6)	0.010 (6)	0.006 (6)
C5	0.040 (7)	0.076 (9)	0.068 (9)	0.014 (6)	−0.001 (6)	0.009 (7)
C6	0.060 (6)	0.056 (5)	0.083 (8)	−0.001 (5)	−0.007 (6)	−0.013 (5)
C7	0.069 (6)	0.071 (6)	0.094 (8)	−0.022 (5)	0.015 (6)	−0.009 (6)
C8	0.052 (5)	0.055 (5)	0.054 (6)	0.002 (4)	0.007 (5)	−0.010 (5)

Geometric parameters (Å, º) top

Cd—N4	2.201 (10)	N3—C8	1.313 (14)
Cd—N2	2.238 (9)	N3—C6	1.392 (16)
Cd—I2	2.7248 (13)	N3—C5	1.544 (14)
Cd—I1	2.7358 (13)	C3—H3A	0.9300
C1—N1	1.429 (16)	N4—C8	1.315 (16)
C1—H1A	0.9600	N4—C7	1.369 (18)
C1—H1B	0.9600	C4—H4A	0.9300
C1—H1C	0.9600	C5—H5A	0.9600
N1—C4	1.355 (16)	C5—H5B	0.9600
N1—C2	1.377 (19)	C5—H5C	0.9600
N2—C4	1.279 (15)	C6—C7	1.360 (18)
N2—C3	1.372 (16)	C6—H6A	0.9300
C2—C3	1.33 (2)	C7—H7A	0.9300
C2—H2A	0.9300	C8—H8A	0.9300

N4—Cd—N2	112.2 (4)	C2—C3—N2	111.2 (14)
N4—Cd—I2	103.7 (3)	C2—C3—H3A	124.4
N2—Cd—I2	109.4 (3)	N2—C3—H3A	124.4
N4—Cd—I1	111.4 (3)	C8—N4—C7	104.1 (11)
N2—Cd—I1	101.1 (3)	C8—N4—Cd	122.5 (9)
I2—Cd—I1	119.20 (5)	C7—N4—Cd	133.3 (9)
N1—C1—H1A	109.5	N2—C4—N1	110.0 (12)
N1—C1—H1B	109.5	N2—C4—H4A	125.0
H1A—C1—H1B	109.5	N1—C4—H4A	125.0
N1—C1—H1C	109.5	N3—C5—H5A	109.5
H1A—C1—H1C	109.5	N3—C5—H5B	109.5
H1B—C1—H1C	109.5	H5A—C5—H5B	109.5
C4—N1—C2	108.3 (10)	N3—C5—H5C	109.5
C4—N1—C1	125.7 (12)	H5A—C5—H5C	109.5
C2—N1—C1	126.0 (12)	H5B—C5—H5C	109.5
C4—N2—C3	106.3 (12)	C7—C6—N3	106.8 (12)
C4—N2—Cd	124.4 (9)	C7—C6—H6A	126.6
C3—N2—Cd	129.2 (10)	N3—C6—H6A	126.6
C3—C2—N1	103.9 (13)	C6—C7—N4	109.3 (12)
C3—C2—H2A	128.0	C6—C7—H7A	125.3
N1—C2—H2A	128.0	N4—C7—H7A	125.3
C8—N3—C6	104.7 (10)	N3—C8—N4	114.9 (12)
C8—N3—C5	129.7 (10)	N3—C8—H8A	122.5
C6—N3—C5	125.6 (10)	N4—C8—H8A	122.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···I1ⁱ	0.96	3.03	3.9797	169

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	[CdI₂(C₄H₆N₂)₂]
M_r	530.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.5570 (9), 14.5615 (14), 14.9585 (19)
V (Å³)	2953.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.64
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.574, 0.579
No. of measured, independent and observed [I > 2σ(I)] reflections	2888, 2768, 1811
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.178, 0.99
No. of reflections	2768
No. of parameters	137
No. of restraints	40
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.85

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···I1ⁱ	0.96	3.03	3.9797	169

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

Acknowledgements

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

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar