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

Mehmet Akkurt; Senem Akkoç; Yetkin Gök; Yılmaz Dağdemir; Muhammad Nawaz Tahir

doi:10.1107/S1600536812012998

. 2012 Apr 13;68(Pt 5):m590–m591. doi: 10.1107/S1600536812012998

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

Mehmet Akkurt ^a,^*, Senem Akkoç ^b, Yetkin Gök ^c, Yılmaz Dağdemir ^a, Muhammad Nawaz Tahir ^d

PMCID: PMC3344334 PMID: 22590100

Abstract

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⋯π interactions contribute to the stabilization of the crystal structure. A very weak π–π 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,
a = 9.1439 (2) Å
b = 18.7633 (4) Å
c = 13.2710 (3) Å
β = 109.899 (1)°
V = 2140.96 (8) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.080
S = 1.01
5288 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012998/sj5223sup1.cif

e-68-0m590-sup1.cif^{(30KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012998/sj5223Isup2.hkl

e-68-0m590-Isup2.hkl^{(259KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg2ⁱ	0.93	2.69	3.507 (4)	147
C22—H22A⋯Cg3ⁱⁱ	0.96	2.80	3.525 (4)	133

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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 İnönü University research fund (BAP 2011/35) for financial support.

supplementary crystallographic information

Comment

N-Heterocyclic carbene complexes (NHCs) have developed significantly in organometallic chemistry and homogenous catalysis since discovered, and have become extremely popular. Silver NHC complexes have particular interest because of their wide use as ligand transfer agents for the synthesis other metal-NHC complexes, catalysis, nanomaterials, and also biological activity as antimicrobial agents (Arduengo et al., 1993; Guerret et al., 1997; Patil et al., 2011; Özdemir et al., 2010b; Liao et al., 2008; Patil et al., 2010; Zhou et al., 2008; Berding et al., 2009).

In connection with our papers on the synthesis of the new complexes with N-heterocyclic carbene ligands, (Yigit et al., 2012; Özdemir et al., 2010c), we report here the crystal structure of the title compound, chlorido-[1-phenyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]silver (I).

In the title compound (I), (Fig. 1), the five- and six-membered rings (N1/N2/C1/C6/C7) and (C1–C6) of the benzimidazole groups are almost co-planar with maximum deviations of -0.012 (2) Å for N1 and 0.012 (3) Å for C6, respectively. The dihedral angle between them is 4.53 (16)°. The C8–C13 phenyl and C15–C20 benzene rings make dihedral angles of 59.59 (11)° and 83.19 (12)°, respectively, with respect to the mean plane of the central N1/N2/C1–C7 benzimidazole ring system, while they make a dihedral angle of 87.92 (14)° with each other. The Ag—C and Ag—Cl single bond lengths are 2.087 (3) Å and 2.3267 (9) Å. The C—Ag—Cl bond angle is 172.84 (7)°. The values of the geometrical parameters of (I) are in agreement with those reported for similar compounds (Allen et al., 1987; Özdemir et al., 2010a).

The crystal structure is stabilized by C—H···π interactions (Table 1) and weak π-π stacking interactions between adjacent (C15–C20: Cg4) benzene rings [Cg4···Cg4(1 - x, 2 - y, 1 - z) = 4.0610 (18) Å]. Fig. 2 shows the packing of (I) in the unit cell, viewed along the a axis.

Experimental

For the originally reported synthesis, see: Yigit et al. (2012); Özdemir et al. (2010c). Single crystals of the title compound were obtained by recrystallization from dichloromethane/hexane at room temperature. (Yields: 0.281 g; 84%. M.p.: 524–525 K).