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

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m590-m591

doi:10.1107/S1600536812012998

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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 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

(Received 23 March 2012; accepted 24 March 2012; online 13 April 2012)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.036
wR(F²) = 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

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
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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012998/sj5223sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Spek, 2009).

Figures top

	Fig. 1. The title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing of the title molecule in the unit cell, viewed along the a axis. H atoms are omitted for clarity.

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

Crystal data top

[AgCl(C₂₄H₂₄N₂)]	F(000) = 984
M_r = 483.77	D_x = 1.501 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3354 reflections
a = 9.1439 (2) Å	θ = 2.4–28.3°
b = 18.7633 (4) Å	µ = 1.08 mm⁻¹
c = 13.2710 (3) Å	T = 296 K
β = 109.899 (1)°	Prism, white
V = 2140.96 (8) Å³	0.35 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5288 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 8.00 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
ω scans	h = −10→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −25→16
T_min = 0.752, T_max = 0.806	l = −17→17
19846 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0308P)² + 0.160P] where P = (F_o² + 2F_c²)/3
5288 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[AgCl(C₂₄H₂₄N₂)]	V = 2140.96 (8) Å³
M_r = 483.77	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1439 (2) Å	µ = 1.08 mm⁻¹
b = 18.7633 (4) Å	T = 296 K
c = 13.2710 (3) Å	0.35 × 0.22 × 0.20 mm
β = 109.899 (1)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.01	Δρ_max = 0.38 e Å⁻³
5288 reflections	Δρ_min = −0.38 e Å⁻³
257 parameters

Special details top

Experimental. M.p.: 524–525 K. n_(CN)=1593.31 cm^{-1. 1}H NMR (DMSO) δ: 2.11, 2.18 (s, 12H, NCH₂C₆H(CH₃)₄-2,3,5,6); 5.61 (s, 2H, NCH₂C₆H(CH₃)₄-2,3,5,6); 6.66–7.87 (m, 10H, Ar-H). ¹³C NMR (DMSO) d: 16.4, 20.8 (NCH₂C₆H(CH₃)₄-2,3,5,6); 55.2 (NCH₂C₆H(CH₃)₄-2,3,5,6); 112.5, 112.8, 124.9, 125.4, 126.8, 129.8, 130.4, 131.3, 132.7, 133.9, 134.6, 138.9 (Ar-C); the carbene carbon was not detected. Analysis calculated for C₂₄H₂₄N₂AgCl: C 59.58, H 5.00, N 5.79%. Found: C 59.56, H 5.01, N 5.78%.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Ag1	0.25184 (3)	0.84953 (1)	0.17444 (2)	0.0476 (1)
Cl1	0.43000 (9)	0.77142 (4)	0.14398 (7)	0.0572 (3)
N1	−0.0611 (3)	0.92849 (11)	0.11403 (17)	0.0370 (7)
N2	0.1099 (3)	0.98412 (11)	0.24355 (18)	0.0419 (8)
C1	−0.1317 (3)	0.99141 (14)	0.1290 (2)	0.0383 (9)
C2	−0.2743 (3)	1.02215 (16)	0.0728 (3)	0.0516 (11)
C3	−0.3022 (4)	1.08812 (18)	0.1066 (3)	0.0633 (14)
C4	−0.1939 (4)	1.12282 (17)	0.1930 (3)	0.0600 (13)
C5	−0.0523 (4)	1.09315 (15)	0.2480 (2)	0.0490 (11)
C6	−0.0233 (3)	1.02675 (14)	0.2127 (2)	0.0400 (9)
C7	0.0885 (3)	0.92485 (14)	0.1829 (2)	0.0407 (9)
C8	−0.1372 (3)	0.87529 (14)	0.0361 (2)	0.0365 (8)
C9	−0.0741 (4)	0.85480 (15)	−0.0403 (2)	0.0458 (10)
C10	−0.1480 (4)	0.80302 (16)	−0.1139 (2)	0.0552 (11)
C11	−0.2846 (4)	0.77302 (16)	−0.1119 (2)	0.0552 (11)
C12	−0.3471 (4)	0.79363 (16)	−0.0351 (3)	0.0536 (11)
C13	−0.2733 (3)	0.84494 (14)	0.0388 (2)	0.0443 (10)
C14	0.2555 (4)	1.00783 (17)	0.3248 (2)	0.0575 (11)
C15	0.3702 (3)	0.95064 (15)	0.3774 (2)	0.0452 (10)
C16	0.3525 (4)	0.91300 (16)	0.4642 (2)	0.0480 (10)
C17	0.4668 (4)	0.86531 (16)	0.5207 (2)	0.0579 (11)
C18	0.5916 (4)	0.85445 (17)	0.4869 (3)	0.0675 (12)
C19	0.6107 (4)	0.8891 (2)	0.4013 (3)	0.0639 (11)
C20	0.4998 (4)	0.93808 (17)	0.3455 (2)	0.0556 (11)
C21	0.2094 (4)	0.9235 (2)	0.4940 (3)	0.0758 (14)
C22	0.4607 (5)	0.8255 (2)	0.6185 (3)	0.0917 (18)
C23	0.7508 (5)	0.8708 (3)	0.3695 (4)	0.115 (2)
C24	0.5189 (5)	0.9767 (2)	0.2499 (3)	0.0853 (17)
H2	−0.34700	0.99920	0.01520	0.0620*
H3	−0.39630	1.11050	0.07090	0.0760*
H4	−0.21850	1.16730	0.21380	0.0720*
H5	0.02020	1.11610	0.30560	0.0590*
H9	0.01720	0.87570	−0.04210	0.0550*
H10	−0.10550	0.78830	−0.16490	0.0660*
H11	−0.33500	0.73880	−0.16250	0.0660*
H12	−0.43850	0.77290	−0.03330	0.0640*
H13	−0.31510	0.85920	0.09040	0.0530*
H14A	0.22980	1.03330	0.38010	0.0690*
H14B	0.30560	1.04140	0.29150	0.0690*
H18	0.66720	0.82180	0.52420	0.0810*
H21A	0.22080	0.96590	0.53640	0.1140*
H21B	0.19590	0.88320	0.53450	0.1140*
H21C	0.12030	0.92820	0.43010	0.1140*
H22A	0.37210	0.79440	0.59830	0.1370*
H22B	0.45230	0.85900	0.67090	0.1370*
H22C	0.55390	0.79790	0.64840	0.1370*
H23A	0.71950	0.83940	0.30890	0.1730*
H23B	0.82820	0.84780	0.42840	0.1730*
H23C	0.79320	0.91370	0.35120	0.1730*
H24A	0.59720	1.01290	0.27490	0.1280*
H24B	0.42190	0.99840	0.20850	0.1280*
H24C	0.54970	0.94330	0.20620	0.1280*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0405 (1)	0.0420 (2)	0.0554 (2)	0.0047 (1)	0.0098 (1)	−0.0002 (1)
Cl1	0.0532 (5)	0.0540 (5)	0.0682 (5)	0.0093 (4)	0.0255 (4)	0.0036 (4)
N1	0.0355 (12)	0.0364 (13)	0.0371 (12)	0.0020 (11)	0.0096 (11)	−0.0018 (10)
N2	0.0431 (14)	0.0362 (14)	0.0375 (13)	−0.0034 (11)	0.0021 (11)	−0.0040 (11)
C1	0.0378 (15)	0.0395 (17)	0.0397 (16)	0.0031 (14)	0.0158 (14)	0.0020 (13)
C2	0.0395 (17)	0.055 (2)	0.060 (2)	0.0036 (15)	0.0164 (16)	0.0027 (16)
C3	0.048 (2)	0.053 (2)	0.090 (3)	0.0156 (17)	0.025 (2)	0.0087 (19)
C4	0.071 (2)	0.0398 (18)	0.083 (3)	0.0081 (19)	0.044 (2)	−0.0009 (18)
C5	0.062 (2)	0.0382 (18)	0.0521 (19)	−0.0015 (16)	0.0265 (18)	−0.0025 (14)
C6	0.0484 (17)	0.0342 (16)	0.0389 (16)	0.0035 (14)	0.0169 (14)	0.0053 (12)
C7	0.0400 (16)	0.0394 (17)	0.0381 (15)	−0.0002 (14)	0.0074 (14)	0.0011 (13)
C8	0.0363 (15)	0.0365 (15)	0.0317 (14)	0.0037 (13)	0.0051 (13)	0.0024 (12)
C9	0.0493 (17)	0.0513 (19)	0.0390 (15)	−0.0054 (15)	0.0179 (14)	−0.0013 (14)
C10	0.074 (2)	0.054 (2)	0.0415 (18)	−0.0010 (18)	0.0246 (18)	−0.0060 (15)
C11	0.063 (2)	0.0477 (19)	0.0437 (18)	−0.0020 (17)	0.0036 (17)	−0.0072 (15)
C12	0.0391 (17)	0.053 (2)	0.066 (2)	−0.0026 (15)	0.0143 (17)	−0.0038 (17)
C13	0.0399 (16)	0.0464 (18)	0.0474 (17)	0.0000 (15)	0.0161 (14)	−0.0064 (14)
C14	0.057 (2)	0.0458 (19)	0.0532 (19)	−0.0074 (17)	−0.0028 (16)	−0.0059 (15)
C15	0.0407 (17)	0.0428 (18)	0.0400 (16)	−0.0072 (14)	−0.0018 (14)	−0.0065 (14)
C16	0.0478 (18)	0.0485 (19)	0.0402 (17)	−0.0133 (15)	0.0054 (15)	−0.0108 (14)
C17	0.066 (2)	0.049 (2)	0.0400 (17)	−0.0114 (17)	−0.0063 (17)	−0.0023 (15)
C18	0.057 (2)	0.056 (2)	0.064 (2)	0.0075 (18)	−0.0126 (19)	−0.0112 (18)
C19	0.0424 (19)	0.074 (2)	0.066 (2)	−0.0081 (19)	0.0065 (18)	−0.022 (2)
C20	0.056 (2)	0.056 (2)	0.0476 (18)	−0.0213 (17)	0.0082 (17)	−0.0109 (16)
C21	0.064 (2)	0.100 (3)	0.061 (2)	−0.014 (2)	0.018 (2)	−0.015 (2)
C22	0.123 (4)	0.074 (3)	0.052 (2)	−0.023 (3)	−0.004 (2)	0.0150 (19)
C23	0.057 (3)	0.153 (5)	0.131 (4)	0.002 (3)	0.026 (3)	−0.044 (4)
C24	0.092 (3)	0.098 (3)	0.068 (3)	−0.037 (3)	0.030 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Ag1—Cl1	2.3267 (9)	C19—C20	1.382 (5)
Ag1—C7	2.087 (3)	C19—C23	1.518 (6)
N1—C1	1.392 (4)	C20—C24	1.522 (5)
N1—C7	1.364 (4)	C2—H2	0.9300
N1—C8	1.435 (3)	C3—H3	0.9300
N2—C6	1.397 (4)	C4—H4	0.9300
N2—C7	1.348 (3)	C5—H5	0.9300
N2—C14	1.468 (4)	C9—H9	0.9300
C1—C2	1.388 (4)	C10—H10	0.9300
C1—C6	1.381 (4)	C11—H11	0.9300
C2—C3	1.370 (5)	C12—H12	0.9300
C3—C4	1.395 (5)	C13—H13	0.9300
C4—C5	1.370 (5)	C14—H14A	0.9700
C5—C6	1.388 (4)	C14—H14B	0.9700
C8—C9	1.381 (4)	C18—H18	0.9300
C8—C13	1.380 (4)	C21—H21A	0.9600
C9—C10	1.380 (4)	C21—H21B	0.9600
C10—C11	1.379 (5)	C21—H21C	0.9600
C11—C12	1.383 (5)	C22—H22A	0.9600
C12—C13	1.376 (4)	C22—H22B	0.9600
C14—C15	1.497 (4)	C22—H22C	0.9600
C15—C16	1.407 (4)	C23—H23A	0.9600
C15—C20	1.407 (5)	C23—H23B	0.9600
C16—C17	1.386 (4)	C23—H23C	0.9600
C16—C21	1.503 (5)	C24—H24A	0.9600
C17—C18	1.376 (5)	C24—H24B	0.9600
C17—C22	1.515 (5)	C24—H24C	0.9600
C18—C19	1.371 (5)

Cl1—Ag1—C7	172.84 (7)	C2—C3—H3	119.00
C1—N1—C7	110.8 (2)	C4—C3—H3	119.00
C1—N1—C8	123.9 (2)	C3—C4—H4	119.00
C7—N1—C8	125.3 (2)	C5—C4—H4	119.00
C6—N2—C7	111.3 (2)	C4—C5—H5	122.00
C6—N2—C14	121.6 (2)	C6—C5—H5	122.00
C7—N2—C14	126.9 (3)	C8—C9—H9	120.00
N1—C1—C2	132.2 (3)	C10—C9—H9	120.00
N1—C1—C6	106.3 (2)	C9—C10—H10	120.00
C2—C1—C6	121.2 (3)	C11—C10—H10	120.00
C1—C2—C3	116.4 (3)	C10—C11—H11	120.00
C2—C3—C4	122.1 (3)	C12—C11—H11	120.00
C3—C4—C5	121.8 (3)	C11—C12—H12	120.00
C4—C5—C6	116.1 (3)	C13—C12—H12	120.00
N2—C6—C1	106.0 (2)	C8—C13—H13	120.00
N2—C6—C5	131.5 (3)	C12—C13—H13	120.00
C1—C6—C5	122.4 (3)	N2—C14—H14A	108.00
Ag1—C7—N1	124.81 (18)	N2—C14—H14B	108.00
Ag1—C7—N2	129.1 (2)	C15—C14—H14A	108.00
N1—C7—N2	105.5 (2)	C15—C14—H14B	108.00
N1—C8—C9	120.1 (3)	H14A—C14—H14B	107.00
N1—C8—C13	119.2 (2)	C17—C18—H18	118.00
C9—C8—C13	120.7 (3)	C19—C18—H18	118.00
C8—C9—C10	119.3 (3)	C16—C21—H21A	109.00
C9—C10—C11	120.2 (3)	C16—C21—H21B	109.00
C10—C11—C12	120.3 (3)	C16—C21—H21C	109.00
C11—C12—C13	119.7 (3)	H21A—C21—H21B	110.00
C8—C13—C12	119.9 (3)	H21A—C21—H21C	109.00
N2—C14—C15	116.2 (2)	H21B—C21—H21C	110.00
C14—C15—C16	119.0 (3)	C17—C22—H22A	110.00
C14—C15—C20	120.5 (3)	C17—C22—H22B	109.00
C16—C15—C20	120.4 (3)	C17—C22—H22C	109.00
C15—C16—C17	119.4 (3)	H22A—C22—H22B	109.00
C15—C16—C21	120.2 (3)	H22A—C22—H22C	109.00
C17—C16—C21	120.4 (3)	H22B—C22—H22C	109.00
C16—C17—C18	118.4 (3)	C19—C23—H23A	109.00
C16—C17—C22	122.7 (3)	C19—C23—H23B	109.00
C18—C17—C22	118.9 (3)	C19—C23—H23C	109.00
C17—C18—C19	123.6 (3)	H23A—C23—H23B	109.00
C18—C19—C20	118.8 (3)	H23A—C23—H23C	110.00
C18—C19—C23	118.7 (4)	H23B—C23—H23C	109.00
C20—C19—C23	122.4 (4)	C20—C24—H24A	109.00
C15—C20—C19	119.3 (3)	C20—C24—H24B	109.00
C15—C20—C24	121.2 (3)	C20—C24—H24C	109.00
C19—C20—C24	119.5 (3)	H24A—C24—H24B	109.00
C1—C2—H2	122.00	H24A—C24—H24C	109.00
C3—C2—H2	122.00	H24B—C24—H24C	110.00

C7—N1—C1—C2	172.8 (3)	C4—C5—C6—C1	−1.7 (4)
C8—N1—C1—C2	−7.1 (5)	N1—C8—C9—C10	179.3 (2)
C7—N1—C1—C6	−2.1 (3)	C9—C8—C13—C12	0.1 (4)
C8—N1—C1—C6	178.0 (2)	C13—C8—C9—C10	−0.5 (4)
C1—N1—C7—Ag1	−169.48 (19)	N1—C8—C13—C12	−179.7 (3)
C8—N1—C7—Ag1	10.4 (4)	C8—C9—C10—C11	1.0 (4)
C1—N1—C7—N2	2.2 (3)	C9—C10—C11—C12	−1.1 (5)
C8—N1—C7—N2	−178.0 (2)	C10—C11—C12—C13	0.8 (5)
C7—N1—C8—C13	122.9 (3)	C11—C12—C13—C8	−0.3 (4)
C1—N1—C8—C9	123.0 (3)	N2—C14—C15—C16	−83.2 (3)
C7—N1—C8—C9	−56.9 (4)	N2—C14—C15—C20	101.2 (3)
C1—N1—C8—C13	−57.2 (4)	C14—C15—C16—C17	−173.2 (3)
C7—N2—C14—C15	−26.7 (4)	C14—C15—C16—C21	7.9 (4)
C6—N2—C7—N1	−1.4 (3)	C20—C15—C16—C17	2.4 (4)
C14—N2—C7—N1	−175.3 (3)	C20—C15—C16—C21	−176.5 (3)
C6—N2—C14—C15	160.1 (3)	C14—C15—C20—C19	174.6 (3)
C14—N2—C6—C1	174.4 (2)	C14—C15—C20—C24	−6.2 (4)
C7—N2—C6—C5	−176.4 (3)	C16—C15—C20—C19	−0.9 (4)
C14—N2—C6—C5	−2.2 (5)	C16—C15—C20—C24	178.3 (3)
C6—N2—C7—Ag1	169.7 (2)	C15—C16—C17—C18	−2.5 (4)
C14—N2—C7—Ag1	−4.1 (4)	C15—C16—C17—C22	176.8 (3)
C7—N2—C6—C1	0.2 (3)	C21—C16—C17—C18	176.4 (3)
N1—C1—C2—C3	−175.7 (3)	C21—C16—C17—C22	−4.3 (5)
N1—C1—C6—C5	178.1 (3)	C16—C17—C18—C19	1.1 (5)
C6—C1—C2—C3	−1.5 (5)	C22—C17—C18—C19	−178.2 (3)
C2—C1—C6—C5	2.5 (4)	C17—C18—C19—C20	0.4 (5)
C2—C1—C6—N2	−174.4 (3)	C17—C18—C19—C23	−178.0 (4)
N1—C1—C6—N2	1.1 (3)	C18—C19—C20—C15	−0.5 (5)
C1—C2—C3—C4	−0.2 (5)	C18—C19—C20—C24	−179.7 (3)
C2—C3—C4—C5	1.0 (6)	C23—C19—C20—C15	177.9 (3)
C3—C4—C5—C6	0.0 (5)	C23—C19—C20—C24	−1.3 (5)
C4—C5—C6—N2	174.4 (3)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	[AgCl(C₂₄H₂₄N₂)]
M_r	483.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.1439 (2), 18.7633 (4), 13.2710 (3)
β (°)	109.899 (1)
V (Å³)	2140.96 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.35 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.752, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	19846, 5288, 3354
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.080, 1.01
No. of reflections	5288
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

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

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

References

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Volume 68| Part 5| May 2012| Pages m590-m591

doi:10.1107/S1600536812012998

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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