Di-μ-acetato-bis­{[3-benzyl-1-(2,4,6-tri­methyl­phen­yl)imidazol-2-ylidene]silver(I)}

The title compound, [Ag₂(C₂H₃O₂)₂(C₁₉H₂₀N₂)₂] (2), was readily synthesized by treatment of 3-benzyl-1-(2,4,6-tri­methyl­phen­yl)imidazolium chloride with silver acetate. The solution structure of the complex was analyzed by NMR spectroscopy, while the solid-state structure was confirmed by single-crystal X-ray diffraction studies. Compound 2 crystallizes in the triclinic space group P, with a silver-to-carbene bond length (Ag—C_NHC) of 2.084 (3) Å. The mol­ecule resides on an inversion center, so that only half of the mol­ecule is crystallographically unique. The planes defined by the two imidazole rings are parallel to each other, but not coplanar [inter­planar distance is 0.662 (19) Å]. The dihedral angles between the imidazole ring and the benzyl and mesityl rings are 77.87 (12) and 72.86 (11)°, respectively. The crystal structure features π–π stacking inter­actions between the benzylic groups of inversion-related (−x + 1, −y + 1, −z + 1) mol­ecules and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.035
• wR factor = 0.080
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1      --O1       .        7.7 s.u.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.101 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         26 Report

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.64 mm
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        69% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Di-µ-acetato-bis{[3-benzyl-1-(2,4,6-trimethylphenyl)imidazol-2-\ ylidene]silver(I)}

Crystal data

[Ag2(C2H3O2)2(C19H20N2)2]	Z = 1
Mr = 886.57	F(000) = 452
Triclinic, P1	Dx = 1.539 Mg m^−3
a = 9.078 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.473 (2) Å	Cell parameters from 3884 reflections
c = 12.236 (3) Å	θ = 2.5–22.8°
α = 65.065 (6)°	µ = 1.07 mm^−1
β = 77.420 (7)°	T = 183 K
γ = 65.229 (7)°	Needle, colorless
V = 956.7 (4) Å^3	0.64 × 0.26 × 0.2 mm

Data collection

Bruker SMART X2S benchtop diffractometer	3354 independent reflections
Radiation source: XOS X-beam microfocus source	2837 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.056
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.783, Tmax = 1.000	k = −12→12
15885 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.9398P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3354 reflections	Δρmax = 0.78 e Å^−3
239 parameters	Δρmin = −0.43 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.67227 (4)	0.80738 (3)	0.56178 (3)	0.03206 (12)
O1	0.3866 (3)	0.9810 (3)	0.5928 (2)	0.0339 (6)
O2	0.1564 (3)	1.0757 (3)	0.6868 (3)	0.0416 (7)
N1	0.8628 (3)	0.4584 (3)	0.6776 (3)	0.0238 (6)
N2	0.8626 (3)	0.5700 (3)	0.7896 (3)	0.0240 (7)
C1	0.8045 (4)	0.5972 (4)	0.6853 (3)	0.0236 (8)
C4	0.8287 (4)	0.4281 (4)	0.5811 (3)	0.0288 (8)
H4A	0.9266	0.3556	0.5593	0.035*
H4B	0.7985	0.5212	0.5105	0.035*
C5	0.6935 (4)	0.3665 (4)	0.6172 (3)	0.0256 (8)
C6	0.7160 (5)	0.2350 (4)	0.6026 (3)	0.0324 (9)
H6	0.8166	0.1818	0.5741	0.039*
C7	0.5909 (5)	0.1818 (4)	0.6298 (4)	0.0376 (10)
H7	0.6080	0.0943	0.6182	0.045*
C8	0.4421 (5)	0.2568 (4)	0.6736 (3)	0.0354 (9)
H8	0.3585	0.2205	0.6925	0.042*
C9	0.4189 (5)	0.3870 (4)	0.6892 (4)	0.0358 (9)
H9	0.3186	0.4383	0.7194	0.043*
C10	0.5421 (4)	0.4429 (4)	0.6607 (3)	0.0320 (9)
H10	0.5234	0.5318	0.6707	0.038*
C2	0.9553 (4)	0.3484 (4)	0.7744 (3)	0.0308 (9)
H2	1.0077	0.2458	0.7880	0.037*
C3	0.9553 (4)	0.4173 (4)	0.8454 (3)	0.0317 (9)
H3	1.0071	0.3719	0.9175	0.038*
C11	0.8354 (4)	0.6847 (4)	0.8361 (3)	0.0239 (8)
C12	0.9159 (4)	0.7872 (4)	0.7781 (3)	0.0253 (8)
C17	1.0252 (5)	0.7852 (5)	0.6671 (4)	0.0416 (10)
H17A	0.9612	0.8202	0.6000	0.062*
H17B	1.1011	0.6837	0.6802	0.062*
H17C	1.0833	0.8503	0.6502	0.062*
C13	0.8878 (4)	0.8938 (4)	0.8275 (3)	0.0290 (8)
H13	0.9419	0.9610	0.7924	0.035*
C14	0.7822 (4)	0.9036 (4)	0.9272 (3)	0.0277 (8)
C15	0.7065 (4)	0.7999 (4)	0.9809 (3)	0.0292 (8)
H15	0.6363	0.8050	1.0481	0.035*
C16	0.7312 (4)	0.6879 (4)	0.9383 (3)	0.0265 (8)
C19	0.6529 (5)	0.5716 (5)	1.0031 (4)	0.0409 (10)
H19A	0.7295	0.4801	1.0545	0.061*
H19B	0.6200	0.5507	0.9450	0.061*
H19C	0.5596	0.6103	1.0510	0.061*
C18	0.7545 (5)	1.0233 (5)	0.9749 (4)	0.0432 (11)
H18A	0.8551	1.0086	1.0004	0.065*
H18B	0.6768	1.0159	1.0423	0.065*
H18C	0.7138	1.1216	0.9125	0.065*
C20	0.2867 (4)	0.9732 (4)	0.6823 (3)	0.0239 (8)
C21	0.3356 (5)	0.8255 (4)	0.7907 (4)	0.0387 (10)
H21A	0.4238	0.8174	0.8277	0.058*
H21B	0.3692	0.7421	0.7651	0.058*
H21C	0.2447	0.8237	0.8479	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0419 (2)	0.01798 (16)	0.03125 (18)	−0.00692 (13)	−0.01203 (13)	−0.00377 (12)
O1	0.0329 (15)	0.0224 (13)	0.0305 (15)	−0.0037 (12)	−0.0004 (13)	−0.0024 (11)
O2	0.0340 (17)	0.0239 (15)	0.0545 (19)	−0.0078 (13)	0.0107 (14)	−0.0124 (14)
N1	0.0225 (16)	0.0170 (15)	0.0297 (17)	−0.0057 (12)	−0.0006 (13)	−0.0088 (13)
N2	0.0244 (16)	0.0179 (15)	0.0290 (17)	−0.0068 (13)	−0.0062 (13)	−0.0067 (13)
C1	0.0231 (19)	0.0199 (18)	0.0257 (19)	−0.0100 (15)	−0.0027 (15)	−0.0040 (15)
C4	0.032 (2)	0.027 (2)	0.031 (2)	−0.0120 (17)	0.0036 (17)	−0.0157 (17)
C5	0.031 (2)	0.0229 (19)	0.0235 (19)	−0.0097 (16)	−0.0057 (16)	−0.0069 (16)
C6	0.041 (2)	0.025 (2)	0.030 (2)	−0.0099 (18)	−0.0005 (18)	−0.0113 (17)
C7	0.049 (3)	0.028 (2)	0.042 (2)	−0.016 (2)	−0.012 (2)	−0.0131 (19)
C8	0.040 (3)	0.036 (2)	0.032 (2)	−0.020 (2)	−0.0085 (19)	−0.0066 (19)
C9	0.028 (2)	0.037 (2)	0.039 (2)	−0.0090 (18)	−0.0012 (18)	−0.0144 (19)
C10	0.031 (2)	0.027 (2)	0.040 (2)	−0.0072 (18)	−0.0014 (18)	−0.0188 (18)
C2	0.026 (2)	0.0164 (18)	0.043 (2)	−0.0017 (16)	−0.0081 (17)	−0.0081 (17)
C3	0.031 (2)	0.0168 (18)	0.039 (2)	−0.0038 (16)	−0.0178 (18)	−0.0008 (17)
C11	0.0218 (19)	0.0195 (18)	0.029 (2)	−0.0038 (15)	−0.0111 (16)	−0.0071 (15)
C12	0.0222 (19)	0.0215 (18)	0.030 (2)	−0.0077 (15)	−0.0031 (16)	−0.0071 (16)
C17	0.045 (3)	0.041 (2)	0.048 (3)	−0.026 (2)	0.012 (2)	−0.022 (2)
C13	0.030 (2)	0.0222 (19)	0.037 (2)	−0.0132 (16)	−0.0048 (17)	−0.0079 (17)
C14	0.023 (2)	0.0252 (19)	0.032 (2)	−0.0050 (16)	−0.0059 (16)	−0.0093 (17)
C15	0.030 (2)	0.034 (2)	0.0240 (19)	−0.0141 (17)	−0.0051 (16)	−0.0074 (17)
C16	0.026 (2)	0.0251 (19)	0.026 (2)	−0.0101 (16)	−0.0092 (16)	−0.0019 (16)
C19	0.051 (3)	0.042 (2)	0.037 (2)	−0.031 (2)	0.000 (2)	−0.008 (2)
C18	0.044 (3)	0.044 (3)	0.052 (3)	−0.018 (2)	−0.002 (2)	−0.026 (2)
C20	0.029 (2)	0.0200 (19)	0.028 (2)	−0.0118 (17)	0.0016 (17)	−0.0122 (16)
C21	0.045 (3)	0.029 (2)	0.033 (2)	−0.0116 (19)	0.0011 (19)	−0.0067 (18)

Geometric parameters (Å, º)

Ag1—O1^i	2.165 (2)	C2—C3	1.343 (5)
Ag1—O1	2.525 (3)	C3—H3	0.9300
Ag1—C1	2.084 (3)	C11—C12	1.407 (5)
O1—Ag1^i	2.165 (2)	C11—C16	1.398 (5)
O1—C20	1.258 (4)	C12—C17	1.500 (5)
O2—C20	1.230 (4)	C12—C13	1.392 (5)
N1—C1	1.360 (4)	C17—H17A	0.9600
N1—C4	1.467 (4)	C17—H17B	0.9600
N1—C2	1.381 (4)	C17—H17C	0.9600
N2—C1	1.360 (4)	C13—H13	0.9300
N2—C3	1.390 (4)	C13—C14	1.390 (5)
N2—C11	1.446 (4)	C14—C15	1.382 (5)
C4—H4A	0.9700	C14—C18	1.505 (5)
C4—H4B	0.9700	C15—H15	0.9300
C4—C5	1.518 (5)	C15—C16	1.393 (5)
C5—C6	1.387 (5)	C16—C19	1.511 (5)
C5—C10	1.390 (5)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C6—C7	1.386 (5)	C19—H19C	0.9600
C7—H7	0.9300	C18—H18A	0.9600
C7—C8	1.371 (6)	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C8—C9	1.379 (5)	C20—C21	1.516 (5)
C9—H9	0.9300	C21—H21A	0.9600
C9—C10	1.387 (5)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
C2—H2	0.9300
Ag1···C1	2.084 (3)	C20···O2	1.230 (4)
Ag1···O1	2.165 (2)	C1···N1	1.360 (4)
O1···C20	1.258 (4)	C2···C3	1.343 (5)
O1^i—Ag1—O1	70.65 (11)	C12—C11—N2	119.1 (3)
C1—Ag1—O1	127.22 (11)	C16—C11—N2	118.4 (3)
C1—Ag1—O1^i	161.35 (12)	C16—C11—C12	122.5 (3)
Ag1^i—O1—Ag1	109.35 (11)	C11—C12—C17	122.3 (3)
C20—O1—Ag1^i	117.5 (2)	C13—C12—C11	116.9 (3)
C20—O1—Ag1	132.6 (2)	C13—C12—C17	120.8 (3)
C1—N1—C4	124.6 (3)	C12—C17—H17A	109.5
C1—N1—C2	111.2 (3)	C12—C17—H17B	109.5
C2—N1—C4	124.1 (3)	C12—C17—H17C	109.5
C1—N2—C3	111.3 (3)	H17A—C17—H17B	109.5
C1—N2—C11	124.8 (3)	H17A—C17—H17C	109.5
C3—N2—C11	123.9 (3)	H17B—C17—H17C	109.5
N1—C1—Ag1	129.0 (2)	C12—C13—H13	118.7
N2—C1—Ag1	126.9 (2)	C14—C13—C12	122.6 (3)
N2—C1—N1	104.0 (3)	C14—C13—H13	118.7
N1—C4—H4A	109.0	C13—C14—C18	120.1 (3)
N1—C4—H4B	109.0	C15—C14—C13	118.1 (3)
N1—C4—C5	112.7 (3)	C15—C14—C18	121.8 (4)
H4A—C4—H4B	107.8	C14—C15—H15	118.7
C5—C4—H4A	109.0	C14—C15—C16	122.6 (4)
C5—C4—H4B	109.0	C16—C15—H15	118.7
C6—C5—C4	120.6 (3)	C11—C16—C19	121.7 (3)
C6—C5—C10	118.1 (3)	C15—C16—C11	117.3 (3)
C10—C5—C4	121.2 (3)	C15—C16—C19	121.0 (3)
C5—C6—H6	119.5	C16—C19—H19A	109.5
C7—C6—C5	121.0 (4)	C16—C19—H19B	109.5
C7—C6—H6	119.5	C16—C19—H19C	109.5
C6—C7—H7	119.6	H19A—C19—H19B	109.5
C8—C7—C6	120.7 (3)	H19A—C19—H19C	109.5
C8—C7—H7	119.6	H19B—C19—H19C	109.5
C7—C8—H8	120.7	C14—C18—H18A	109.5
C7—C8—C9	118.7 (4)	C14—C18—H18B	109.5
C9—C8—H8	120.7	C14—C18—H18C	109.5
C8—C9—H9	119.4	H18A—C18—H18B	109.5
C8—C9—C10	121.3 (4)	H18A—C18—H18C	109.5
C10—C9—H9	119.4	H18B—C18—H18C	109.5
C5—C10—H10	119.9	O1—C20—C21	115.9 (3)
C9—C10—C5	120.2 (3)	O2—C20—O1	124.6 (3)
C9—C10—H10	119.9	O2—C20—C21	119.5 (3)
N1—C2—H2	126.4	C20—C21—H21A	109.5
C3—C2—N1	107.2 (3)	C20—C21—H21B	109.5
C3—C2—H2	126.4	C20—C21—H21C	109.5
N2—C3—H3	126.8	H21A—C21—H21B	109.5
C2—C3—N2	106.4 (3)	H21A—C21—H21C	109.5
C2—C3—H3	126.8	H21B—C21—H21C	109.5

Symmetry code: (i) −x+1, −y+2, −z+1.