Bis{μ-1-[(2-ethyl-1H-imidazol-1-yl)meth­yl]-1H-benzotriazole}bis­(iodido­cadmium)

Wang, X.; Niu, J.

doi:10.1107/S1600536811021179

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m882

doi:10.1107/S1600536811021179

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Bis{μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole}bis(iodidocadmium)

Xia Wang ^a ^* and Jun-long Niu ^b

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: wangxiawx83@yahoo.com.cn

(Received 30 May 2011; accepted 1 June 2011; online 11 June 2011)

The dinuclear title complex, [Cd₂I₄(C₁₂H₁₃N₅)₂], lies on a crystallographic center of inversion. The Cd^II atom is four-coordinated by two N atoms from two 1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole (bmei) ligands and two terminal I atoms in a distorted tetrahedral coordination environment. The Cd^II atoms are connected to each other by two bridging bmei ligands. The benzotriazole rings in adjacent molecules are almost parallel, with an average interplanar distance of 3.3400 (2) Å and a centroid–centroid distance of 4.852 (2) Å.

Related literature

For related structures, see: Meng et al. (2009 ); Huang et al. (2006 ); Zhai et al. (2006 ); Wang et al. (2010 ).

Experimental

Crystal data

[Cd₂I₄(C₁₂H₁₃N₅)₂]
M_r = 1186.95
Triclinic, $[P \overline 1]$
a = 7.8323 (4) Å
b = 10.0657 (6) Å
c = 11.2335 (7) Å
α = 78.849 (5)°
β = 86.020 (5)°
γ = 77.538 (5)°
V = 848.08 (9) Å³
Z = 1
Mo Kα radiation
μ = 4.93 mm⁻¹
T = 290 K
0.25 × 0.21 × 0.15 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: Gaussian [numerical absorption correction based on Gaussian integration over a multifaceted crystal model (CrysAlis PRO; Agilent, 2010 )] T_min = 0.287, T_max = 0.487
13998 measured reflections
3462 independent reflections
2961 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.061
S = 1.08
3462 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021179/zq2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021179/zq2107Isup2.hkl

checkCIF report

Comment top

Imidazole and benzotriazole derivatives have been widely used in the construction of complexes since they can act as polydentate ligands and function as bridging ligands (Meng et al., 2009; Huang et al., 2006). The Cd^II atom is a good model atom to construct complexes owing to its property to form bonds with different donors simultaneously, and to its various modes (Zhai et al., 2006; Wang et al., 2010). In this work, through the reaction of 1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole (bmei) with cadmium iodide at room temperature, we obtained the title complex [Cd₂(C₁₂H₁₃N₅)₂I₂], which is reported here.

The dinuclear title complex, [Cd₂(C₁₂H₁₃N₅)₂I₂], lies on a crystallographic center of inversion. The Cd^II atom is four-coordinated by two N atoms from two 1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole (bmei) ligands and two terminal I atoms in a distorted tetrahedral coordination environment. The Cd^II atoms are connected by two bridging bmei ligands (Fig. 1). The distance between two Cd atoms bridged by two bmei ligands is 8.4983 (7) Å. In addition, the benzotriazole rings in adjacent molecules are almost parallel with an average interplanar distance of 3.3400 (2) Å and a centroid-centroid distance of 4.852 (2) Å.

Related literature top

For related structures, see: Meng et al. (2009); Huang et al. (2006); Zhai et al. (2006); Wang et al. (2010).

Experimental top

The ligand 1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole (0.04 mmol, 0.0096 g) in methanol (6 ml) was added dropwise to a methanol solution (6 ml) of CdI2 (0.04 mmol, 0.0146 g) in methanol. The resulting solution was allowed to stand at room temperature. After two weeks good quality colourless crystals were obtained from the dried in air.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the title complex, showing the labeling of the 30% probability ellipsolids (all H atoms have been omitted for clarity). Symmetry code: (A) -x + 1, -y + 2, -z.
	Fig. 2. A view of the crystal packing along the a axis. All H atoms are omitted for clarity.

Bis{µ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H- benzotriazole}bis(iodidocadmium) top

Crystal data top

[Cd₂I₄(C₁₂H₁₃N₅)₂]	Z = 1
M_r = 1186.95	F(000) = 548
Triclinic, P1	D_x = 2.324 Mg m⁻³
a = 7.8323 (4) Å	Mo Kα radiation, λ = 0.7107 Å
b = 10.0657 (6) Å	Cell parameters from 6849 reflections
c = 11.2335 (7) Å	θ = 3.0–26.3°
α = 78.849 (5)°	µ = 4.93 mm⁻¹
β = 86.020 (5)°	T = 290 K
γ = 77.538 (5)°	Prismatic, colourless
V = 848.08 (9) Å³	0.25 × 0.21 × 0.15 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3462 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 16.2312 pixels mm^-1	θ_max = 26.3°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: gaussian [numerical absorption correction based on Gaussian integration over a multifaceted crystal model (CrysAlis PRO; Agilent, 2010)]	k = −12→12
T_min = 0.287, T_max = 0.487	l = −14→14
13998 measured reflections

Refinement top

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.026P)² + 0.3471P] where P = (F_o² + 2F_c²)/3
3462 reflections	(Δ/σ)_max = 0.002
182 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

[Cd₂I₄(C₁₂H₁₃N₅)₂]	γ = 77.538 (5)°
M_r = 1186.95	V = 848.08 (9) Å³
Triclinic, P1	Z = 1
a = 7.8323 (4) Å	Mo Kα radiation
b = 10.0657 (6) Å	µ = 4.93 mm⁻¹
c = 11.2335 (7) Å	T = 290 K
α = 78.849 (5)°	0.25 × 0.21 × 0.15 mm
β = 86.020 (5)°

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3462 independent reflections
Absorption correction: gaussian [numerical absorption correction based on Gaussian integration over a multifaceted crystal model (CrysAlis PRO; Agilent, 2010)]	2961 reflections with I > 2σ(I)
T_min = 0.287, T_max = 0.487	R_int = 0.031
13998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.08	Δρ_max = 0.82 e Å⁻³
3462 reflections	Δρ_min = −1.05 e Å⁻³
182 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
I1	0.49488 (4)	1.31204 (3)	0.40337 (2)	0.04897 (9)
I2	−0.04748 (4)	1.42680 (3)	0.22432 (3)	0.06153 (11)
Cd1	0.27758 (4)	1.26989 (3)	0.24333 (2)	0.03657 (9)
N1	0.2561 (4)	1.0409 (3)	0.2834 (3)	0.0385 (7)
N2	0.4017 (4)	0.9559 (3)	0.2627 (3)	0.0389 (7)
N3	0.3713 (4)	0.8276 (3)	0.2862 (3)	0.0350 (7)
N4	0.5058 (4)	0.7062 (3)	0.1294 (3)	0.0354 (7)
N5	0.5744 (4)	0.7249 (3)	−0.0641 (3)	0.0370 (7)
C1	0.2006 (5)	0.8280 (4)	0.3244 (3)	0.0343 (8)
C2	0.1274 (5)	0.9679 (4)	0.3215 (3)	0.0356 (8)
C3	−0.0491 (5)	1.0113 (4)	0.3544 (4)	0.0451 (10)
H3	−0.1003	1.1043	0.3512	0.054*
C4	−0.1422 (6)	0.9082 (5)	0.3916 (4)	0.0514 (11)
H4	−0.2598	0.9322	0.4139	0.062*
C5	−0.0643 (6)	0.7676 (5)	0.3966 (4)	0.0525 (11)
H5	−0.1322	0.7018	0.4236	0.063*
C6	0.1076 (6)	0.7234 (4)	0.3635 (4)	0.0469 (10)
H6	0.1583	0.6303	0.3670	0.056*
C7	0.5056 (5)	0.7136 (4)	0.2573 (3)	0.0421 (9)
H7A	0.4851	0.6274	0.3059	0.051*
H7B	0.6192	0.7258	0.2772	0.051*
C8	0.3756 (5)	0.6688 (4)	0.0752 (4)	0.0432 (9)
H8	0.2762	0.6414	0.1132	0.052*
C9	0.4206 (5)	0.6798 (4)	−0.0435 (4)	0.0440 (9)
H9	0.3570	0.6598	−0.1023	0.053*
C10	0.6246 (5)	0.7411 (3)	0.0414 (3)	0.0330 (8)
C11	0.7851 (5)	0.7927 (4)	0.0590 (4)	0.0442 (9)
H11B	0.8741	0.7642	−0.0007	0.053*
H11A	0.8297	0.7494	0.1388	0.053*
C12	0.7549 (6)	0.9494 (4)	0.0479 (4)	0.0564 (11)
H12B	0.7143	0.9933	−0.0316	0.085*
H12C	0.8626	0.9748	0.0607	0.085*
H12A	0.6687	0.9786	0.1078	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04834 (17)	0.06438 (19)	0.03873 (15)	−0.02051 (14)	−0.00434 (12)	−0.00950 (13)
I2	0.04034 (16)	0.04634 (17)	0.0956 (3)	−0.00025 (13)	−0.00964 (16)	−0.01437 (16)
Cd1	0.03734 (16)	0.03522 (15)	0.03821 (16)	−0.00826 (12)	0.00067 (12)	−0.00907 (12)
N1	0.0398 (18)	0.0340 (17)	0.0428 (18)	−0.0096 (14)	0.0045 (15)	−0.0097 (14)
N2	0.0433 (18)	0.0328 (17)	0.0398 (17)	−0.0086 (14)	0.0052 (15)	−0.0065 (14)
N3	0.0410 (17)	0.0326 (16)	0.0298 (15)	−0.0068 (14)	0.0026 (13)	−0.0037 (12)
N4	0.0390 (17)	0.0341 (16)	0.0343 (16)	−0.0070 (14)	0.0003 (14)	−0.0103 (13)
N5	0.0422 (18)	0.0361 (17)	0.0344 (17)	−0.0120 (14)	0.0013 (14)	−0.0074 (13)
C1	0.039 (2)	0.038 (2)	0.0278 (18)	−0.0134 (17)	−0.0008 (16)	−0.0064 (15)
C2	0.039 (2)	0.040 (2)	0.0297 (18)	−0.0114 (17)	0.0007 (16)	−0.0074 (16)
C3	0.040 (2)	0.050 (2)	0.047 (2)	−0.0078 (19)	0.0020 (19)	−0.0138 (19)
C4	0.038 (2)	0.071 (3)	0.049 (2)	−0.019 (2)	0.0026 (19)	−0.015 (2)
C5	0.053 (3)	0.061 (3)	0.053 (3)	−0.036 (2)	0.004 (2)	−0.007 (2)
C6	0.058 (3)	0.042 (2)	0.045 (2)	−0.020 (2)	0.003 (2)	−0.0083 (18)
C7	0.046 (2)	0.038 (2)	0.038 (2)	0.0005 (18)	−0.0032 (18)	−0.0041 (17)
C8	0.042 (2)	0.042 (2)	0.050 (2)	−0.0147 (18)	0.0083 (19)	−0.0142 (19)
C9	0.044 (2)	0.047 (2)	0.049 (2)	−0.0176 (19)	0.0011 (19)	−0.0195 (19)
C10	0.0353 (19)	0.0265 (17)	0.037 (2)	−0.0068 (15)	0.0012 (16)	−0.0058 (15)
C11	0.039 (2)	0.051 (2)	0.046 (2)	−0.0116 (19)	−0.0028 (18)	−0.0127 (19)
C12	0.055 (3)	0.059 (3)	0.062 (3)	−0.028 (2)	−0.001 (2)	−0.011 (2)

Geometric parameters (Å, º) top

I1—Cd1	2.7094 (4)	C3—C4	1.379 (6)
I2—Cd1	2.6892 (4)	C4—H4	0.9300
Cd1—N1	2.302 (3)	C4—C5	1.406 (6)
Cd1—N5ⁱ	2.250 (3)	C5—H5	0.9300
N1—N2	1.306 (4)	C5—C6	1.373 (6)
N1—C2	1.371 (5)	C6—H6	0.9300
N2—N3	1.337 (4)	C7—H7A	0.9700
N3—C1	1.375 (5)	C7—H7B	0.9700
N3—C7	1.451 (5)	C8—H8	0.9300
N4—C7	1.452 (5)	C8—C9	1.345 (5)
N4—C8	1.376 (5)	C9—H9	0.9300
N4—C10	1.359 (5)	C10—C11	1.499 (5)
N5—Cd1ⁱ	2.250 (3)	C11—H11B	0.9700
N5—C9	1.367 (5)	C11—H11A	0.9700
N5—C10	1.323 (4)	C11—C12	1.525 (6)
C1—C2	1.396 (5)	C12—H12B	0.9600
C1—C6	1.393 (5)	C12—H12C	0.9600
C2—C3	1.403 (5)	C12—H12A	0.9600
C3—H3	0.9300

I2—Cd1—I1	118.809 (14)	C4—C3—C2	116.1 (4)
N1—Cd1—I1	109.18 (8)	C4—C3—H3	121.9
N1—Cd1—I2	108.30 (8)	C4—C5—H5	118.6
N1—N2—N3	107.9 (3)	C5—C4—H4	119.1
N1—C2—C1	107.6 (3)	C5—C6—C1	115.2 (4)
N1—C2—C3	131.4 (4)	C5—C6—H6	122.4
N2—N1—Cd1	113.7 (2)	C6—C1—C2	123.0 (4)
N2—N1—C2	109.7 (3)	C6—C5—C4	122.8 (4)
N2—N3—C1	111.1 (3)	C6—C5—H5	118.6
N2—N3—C7	119.6 (3)	H7A—C7—H7B	108.0
N3—C1—C2	103.7 (3)	C8—N4—C7	124.5 (3)
N3—C1—C6	133.2 (4)	C8—C9—N5	109.3 (4)
N3—C7—N4	110.9 (3)	C8—C9—H9	125.4
N3—C7—H7A	109.5	C9—N5—Cd1ⁱ	122.4 (3)
N3—C7—H7B	109.5	C9—C8—N4	106.4 (4)
N4—C7—H7A	109.5	C9—C8—H8	126.8
N4—C7—H7B	109.5	C10—N4—C7	127.6 (3)
N4—C8—H8	126.8	C10—N4—C8	107.8 (3)
N4—C10—C11	126.0 (3)	C10—N5—Cd1ⁱ	129.4 (3)
N5ⁱ—Cd1—I1	106.59 (8)	C10—N5—C9	107.5 (3)
N5ⁱ—Cd1—I2	112.86 (8)	C10—C11—H11B	108.7
N5ⁱ—Cd1—N1	99.31 (11)	C10—C11—H11A	108.7
N5—C9—H9	125.4	C10—C11—C12	114.1 (3)
N5—C10—N4	109.1 (3)	C11—C12—H12B	109.5
N5—C10—C11	124.9 (3)	C11—C12—H12C	109.5
C1—N3—C7	128.9 (3)	C11—C12—H12A	109.5
C1—C2—C3	121.0 (4)	H11B—C11—H11A	107.6
C1—C6—H6	122.4	C12—C11—H11B	108.7
C2—N1—Cd1	136.6 (2)	C12—C11—H11A	108.7
C2—C3—H3	121.9	H12B—C12—H12C	109.5
C3—C4—H4	119.1	H12B—C12—H12A	109.5
C3—C4—C5	121.9 (4)	H12C—C12—H12A	109.5

I1—Cd1—N1—N2	−66.6 (2)	N5ⁱ—Cd1—N1—C2	−133.4 (4)
I1—Cd1—N1—C2	115.3 (3)	N5—C10—C11—C12	90.2 (5)
I2—Cd1—N1—N2	162.7 (2)	C1—N3—C7—N4	90.9 (4)
I2—Cd1—N1—C2	−15.4 (4)	C1—C2—C3—C4	1.4 (6)
Cd1—N1—N2—N3	−178.4 (2)	C2—N1—N2—N3	0.2 (4)
Cd1—N1—C2—C1	178.3 (3)	C2—C1—C6—C5	1.6 (6)
Cd1—N1—C2—C3	−1.7 (6)	C2—C3—C4—C5	0.2 (6)
Cd1ⁱ—N5—C9—C8	171.0 (2)	C3—C4—C5—C6	−1.0 (7)
Cd1ⁱ—N5—C10—N4	−169.5 (2)	C4—C5—C6—C1	0.1 (6)
Cd1ⁱ—N5—C10—C11	11.7 (5)	C6—C1—C2—N1	177.6 (3)
N1—N2—N3—C1	−0.5 (4)	C6—C1—C2—C3	−2.4 (6)
N1—N2—N3—C7	172.9 (3)	C7—N3—C1—C2	−172.0 (3)
N1—C2—C3—C4	−178.6 (4)	C7—N3—C1—C6	10.3 (7)
N2—N1—C2—C1	0.1 (4)	C7—N4—C8—C9	177.7 (3)
N2—N1—C2—C3	−179.9 (4)	C7—N4—C10—N5	−177.4 (3)
N2—N3—C1—C2	0.5 (4)	C7—N4—C10—C11	1.3 (6)
N2—N3—C1—C6	−177.1 (4)	C8—N4—C7—N3	−69.3 (5)
N2—N3—C7—N4	−81.1 (4)	C8—N4—C10—N5	−0.9 (4)
N3—C1—C2—N1	−0.4 (4)	C8—N4—C10—C11	177.9 (3)
N3—C1—C2—C3	179.6 (3)	C9—N5—C10—N4	0.4 (4)
N3—C1—C6—C5	178.9 (4)	C9—N5—C10—C11	−178.4 (3)
N4—C8—C9—N5	−0.8 (4)	C10—N4—C7—N3	106.8 (4)
N4—C10—C11—C12	−88.4 (5)	C10—N4—C8—C9	1.0 (4)
N5ⁱ—Cd1—N1—N2	44.7 (3)	C10—N5—C9—C8	0.3 (4)

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Cd₂I₄(C₁₂H₁₃N₅)₂]
M_r	1186.95
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	7.8323 (4), 10.0657 (6), 11.2335 (7)
α, β, γ (°)	78.849 (5), 86.020 (5), 77.538 (5)
V (Å³)	848.08 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.93
Crystal size (mm)	0.25 × 0.21 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini diffractometer
Absorption correction	Gaussian [numerical absorption correction based on Gaussian integration over a multifaceted crystal model (CrysAlis PRO; Agilent, 2010)]
T_min, T_max	0.287, 0.487
No. of measured, independent and observed [I > 2σ(I)] reflections	13998, 3462, 2961
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.061, 1.08
No. of reflections	3462
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −1.05

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Acknowledgements

The authors thank Professor Hong-Wei Hou and Yu Zhu of Zhengzhou University for their help.

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