Chlorido[1-phenyl-3-(2,3,5,6-tetra­methyl­benz­yl)benzimidazol-2-yl­idene]silver(I)

Akkurt, M.; Akkoç, S.; Gök, Y.; Dağdemir, Y.; Tahir, M.N.

doi:10.1107/S1600536812012998

Volume 68
Part 5
Pages m590-m591
May 2012

Received 23 March 2012
Accepted 24 March 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.036
wR = 0.080
Data-to-parameter ratio = 20.6
Details

Chlorido[1-phenyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]silver(I)

Mehmet Akkurt,^a ^* Senem Akkoç,^b Yetkin Gök,^c Yilmaz Dagdemir ^a and Muhammad Nawaz Tahir ^d

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Chemistry, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, and ^dDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, [AgCl(C₂₄H₂₄N₂)], the terminal phenyl and tetramethylbenzene rings [which form a dihedral angle of 87.92 (14)°] make dihedral angles of 59.59 (11) and 83.19 (12)° with respect to the central benzimidazole ring system. The Ag-C and Ag-Cl single-bond lengths are 2.087 (3) and 2.3267 (9) Å. The C-Ag-Cl bond angle is 172.84 (7)°. C-H [pi] interactions contribute to the stabilization of the crystal structure. A very weak [pi] - [pi] stacking interaction between adjacent tetramethylbenzene rings [centroid-centroid distance = 4.0610 (18) Å] is also observed.

Related literature

For the synthesis, see: Yigit et al. (2012); Özdemir et al. (2010c). For applications of silver N-heterocyclic carbene complexes in synthesis, catalysis, nanomaterials, and biology, see: Arduengo et al. (1993); Guerret et al. (1997); Patil et al. (2011); Özdemir et al. (2010b); Liao et al. (2008). For related compounds, see: Patil et al. (2010); Zhou et al. (2008); Berding et al. (2009). For bond-length data, see: Özdemir et al. (2010a); Allen et al. (1987).

Experimental

Crystal data

[AgCl(C₂₄H₂₄N₂)]
M_r = 483.77
Monoclinic, P 2₁ /n
a = 9.1439 (2) Å
b = 18.7633 (4) Å
c = 13.2710 (3) Å
= 109.899 (1)°
V = 2140.96 (8) Å³
Z = 4
Mo K radiation
= 1.08 mm^-1
T = 296 K
0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.752, T_max = 0.806
19846 measured reflections
5288 independent reflections
3354 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.080
S = 1.01
5288 reflections
257 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 benzene and C8-C13 phenyl rings, respectively.

D-HA	D-H	HA	DA	D-HA
C9-H9Cg2ⁱ	0.93	2.69	3.507 (4)	147
C22-H22ACg3ⁱⁱ	0.96	2.80	3.525 (4)	133
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5223 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. We also thank the Inönü University research fund (BAP 2011/35) for financial support.

References

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metal-organic compounds