Chlorido[1-phenyl-3-(2,3,5,6-tetra-methyl-benz-yl)benzimidazol-2-yl-idene]silver(I).

In the title compound, [AgCl(C(24)H(24)N(2))], the terminal phenyl and tetra-methyl-benzene 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 inter-actions contribute to the stabilization of the crystal structure. A very weak π-π stacking inter-action between adjacent tetra-methyl-benzene 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 = 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

Δρmax = 0.38 e Å−3

Δρmin = −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.

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

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

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

[AgCl(C24H24N2)]	F(000) = 984
Mr = 483.77	Dx = 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

Bruker Kappa APEXII CCD diffractometer	5288 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.00 pixels mm-1	θmax = 28.3°, θmin = 2.4°
ω scans	h = −10→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −25→16
Tmin = 0.752, Tmax = 0.806	l = −17→17
19846 measured reflections

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(Fo2) + (0.0308P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
5288 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. M.p.: 524–525 K. n(CN)=1593.31 cm-1. 1H 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .