μ(3)-Chlorido-tris-(bis-{1-[2-(dimethyl-amino)-eth-yl]-3-methyl-imidazol-2-yl-idene}silver(I)) dichloride.

In the crystal structure of the title compound, [Ag(3)Cl(C(8)H(15)N(3))(6)]Cl(2), the Ag(I) ion, which is located on a twofold rotation axis, exists in a T-shape coordination environment. Two carbene C atoms of the N-heterocyclic carbene (NHC) ligands are bonded tightly forming a slightly bent [Ag(NHC)(2)](+) cation [C-Ag-C angle = 162.80 (18)°]. Three of these complex cations are further aggregated by one bridging chloride anion, which is lying on a threefold rotoinversion axis and is only loosely binding to the Ag(+) ions. The N atom of the amine group is not engaged in any coordinative bond.

Related literature

For related literature concerning similar N-heterocyclic carbenes, see: Topf, Hirtenlehner, Fleck et al. (2011 ▶); Topf, Hirtenlehner & Monkowius (2011 ▶); Leitner et al. (2011 ▶). For related structures, see: Hirtenlehner et al. (2011 ▶); Wang et al. (2006 ▶). For details of the preparation, see: Topf, Hirtenlehner, Zabel et al. (2011 ▶).

Experimental

Crystal data

[Ag3Cl(C8H15N3)6]Cl2

M = 1349.34

Trigonal,

a = 12.7300 (16) Å

c = 66.789 (12) Å

V = 9373 (2) Å3

Z = 6

Mo Kα radiation

μ = 1.11 mm−1

T = 200 K

0.50 × 0.36 × 0.31 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.61, T max = 0.73

18593 measured reflections

1859 independent reflections

1590 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.03

1859 reflections

113 parameters

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 and GIS (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 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004473/bt5811sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004473/bt5811Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004473/bt5811Isup3.cdx

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

[Ag3Cl(C8H15N3)2]Cl2	F(000) = 4176
Mr = 1349.34	Dx = 1.434 Mg m−3
Trigonal, R3c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7300 (16) Å	µ = 1.11 mm−1
c = 66.789 (12) Å	T = 200 K
V = 9373 (2) Å3	Prism, colourless
Z = 6	0.50 × 0.36 × 0.31 mm

Bruker SMART X2S diffractometer	1859 independent reflections
Radiation source: sealed MicroFocus tube	1590 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.060
ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→14
Tmin = 0.61, Tmax = 0.73	k = −15→15
18593 measured reflections	l = −79→79

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0504P)2 + 47.4314P] where P = (Fo2 + 2Fc2)/3
1859 reflections	(Δ/σ)max = 0.001
113 parameters	Δρmax = 1.28 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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	0.90085 (3)	0.3333	0.0833	0.03038 (16)
C6	1.1504 (3)	0.5164 (4)	0.05466 (6)	0.0422 (9)
H6A	1.1374	0.5764	0.0617	0.063*
H6B	1.2184	0.558	0.0453	0.063*
H6C	1.1689	0.4703	0.0644	0.063*
C1	0.9354 (3)	0.3530 (3)	0.05243 (5)	0.0257 (7)
N2	0.8610 (3)	0.2965 (3)	0.03679 (4)	0.0284 (6)
C5	0.7252 (4)	0.0798 (4)	0.03044 (7)	0.0543 (11)
H5A	0.6394	0.0146	0.0315	0.065*
H5B	0.7471	0.0909	0.0161	0.065*
N1	1.0411 (2)	0.4340 (2)	0.04359 (4)	0.0271 (6)
C4	0.7366 (3)	0.1961 (4)	0.03843 (6)	0.0388 (9)
H4A	0.682	0.2158	0.0308	0.047*
H4B	0.7112	0.1848	0.0526	0.047*
C3	0.9192 (3)	0.3417 (3)	0.01870 (6)	0.0358 (9)
H3	0.8853	0.3163	0.0057	0.043*
C2	1.0327 (3)	0.4284 (3)	0.02306 (5)	0.0341 (8)
H2	1.095	0.4766	0.0138	0.041*
N3	0.8016 (3)	0.0410 (3)	0.04089 (6)	0.0475 (9)
C8	0.7953 (7)	−0.0580 (6)	0.02927 (11)	0.101 (2)
H8A	0.842	−0.0898	0.036	0.151*
H8B	0.829	−0.0286	0.0159	0.151*
H8C	0.7104	−0.1226	0.028	0.151*
C9	0.7645 (7)	0.0065 (6)	0.06074 (11)	0.114 (3)
H9A	0.772	0.0761	0.0682	0.172*
H9B	0.8157	−0.0217	0.067	0.172*
H9C	0.6797	−0.0591	0.0609	0.172*
Cl1	0.6667	0.3333	0.0833	0.0307 (4)
Cl2	0.3333	0.6667	0.00857 (2)	0.0344 (3)

	U11	U22	U33	U12	U13	U23
Ag1	0.0353 (2)	0.0290 (2)	0.0247 (2)	0.01451 (11)	0.00056 (7)	0.00112 (14)
C6	0.032 (2)	0.035 (2)	0.048 (2)	0.0078 (17)	−0.0022 (17)	−0.0035 (17)
C1	0.0288 (17)	0.0288 (17)	0.0267 (18)	0.0197 (15)	−0.0005 (14)	0.0007 (13)
N2	0.0256 (14)	0.0345 (16)	0.0289 (16)	0.0180 (13)	0.0007 (12)	−0.0018 (12)
C5	0.040 (2)	0.053 (3)	0.057 (3)	0.013 (2)	−0.003 (2)	−0.005 (2)
N1	0.0246 (14)	0.0259 (14)	0.0314 (15)	0.0131 (12)	0.0013 (11)	0.0016 (12)
C4	0.0238 (18)	0.046 (2)	0.044 (2)	0.0161 (17)	−0.0016 (15)	−0.0062 (18)
C3	0.040 (2)	0.048 (2)	0.0245 (19)	0.0255 (18)	0.0000 (15)	0.0000 (15)
C2	0.039 (2)	0.039 (2)	0.0290 (19)	0.0233 (17)	0.0095 (15)	0.0072 (15)
N3	0.0411 (19)	0.0327 (18)	0.061 (2)	0.0126 (15)	−0.0096 (17)	−0.0030 (16)
C8	0.108 (5)	0.066 (4)	0.121 (6)	0.039 (4)	0.011 (4)	−0.010 (4)
C9	0.132 (7)	0.081 (5)	0.069 (4)	0.007 (4)	−0.034 (4)	0.012 (3)
Cl1	0.0299 (6)	0.0299 (6)	0.0323 (10)	0.0150 (3)	0	0
Cl2	0.0356 (5)	0.0356 (5)	0.0319 (7)	0.0178 (3)	0	0

Ag1—C1i	2.099 (3)	N1—C2	1.374 (5)
Ag1—C1	2.099 (3)	C4—H4A	0.99
C6—N1	1.458 (5)	C4—H4B	0.99
C6—H6A	0.98	C3—C2	1.340 (5)
C6—H6B	0.98	C3—H3	0.95
C6—H6C	0.98	C2—H2	0.95
C1—N2	1.350 (5)	N3—C9	1.402 (8)
C1—N1	1.355 (4)	N3—C8	1.447 (7)
N2—C3	1.383 (5)	C8—H8A	0.98
N2—C4	1.459 (5)	C8—H8B	0.98
C5—N3	1.469 (6)	C8—H8C	0.98
C5—C4	1.511 (6)	C9—H9A	0.98
C5—H5A	0.99	C9—H9B	0.98
C5—H5B	0.99	C9—H9C	0.98
C1i—Ag1—C1	162.80 (18)	N2—C4—H4B	109.4
N1—C6—H6A	109.5	C5—C4—H4B	109.4
N1—C6—H6B	109.5	H4A—C4—H4B	108.0
H6A—C6—H6B	109.5	C2—C3—N2	106.6 (3)
N1—C6—H6C	109.5	C2—C3—H3	126.7
H6A—C6—H6C	109.5	N2—C3—H3	126.7
H6B—C6—H6C	109.5	C3—C2—N1	106.5 (3)
N2—C1—N1	103.5 (3)	C3—C2—H2	126.8
N2—C1—Ag1	130.4 (3)	N1—C2—H2	126.8
N1—C1—Ag1	126.0 (2)	C9—N3—C8	111.8 (5)
C1—N2—C3	111.5 (3)	C9—N3—C5	112.2 (5)
C1—N2—C4	125.0 (3)	C8—N3—C5	106.3 (4)
C3—N2—C4	123.4 (3)	N3—C8—H8A	109.5
N3—C5—C4	114.0 (3)	N3—C8—H8B	109.5
N3—C5—H5A	108.8	H8A—C8—H8B	109.5
C4—C5—H5A	108.8	N3—C8—H8C	109.5
N3—C5—H5B	108.8	H8A—C8—H8C	109.5
C4—C5—H5B	108.8	H8B—C8—H8C	109.5
H5A—C5—H5B	107.7	N3—C9—H9A	109.5
C1—N1—C2	111.9 (3)	N3—C9—H9B	109.5
C1—N1—C6	123.7 (3)	H9A—C9—H9B	109.5
C2—N1—C6	124.4 (3)	N3—C9—H9C	109.5
N2—C4—C5	111.3 (3)	H9A—C9—H9C	109.5
N2—C4—H4A	109.4	H9B—C9—H9C	109.5
C5—C4—H4A	109.4