Crystal structure of di-μ-iodido-bis-{[1,3-bis-(2,6-diiso-propyl-phen-yl)imidazol-2-yl-idene]lithium}.

In the title binuclear complex, [Li2(C27H36N2)2I2], the unique Li(I) cation is coordinated by two iodide anions and one yl-idene C atom from a 1,3-bis-(2,6-diiso-propyl-phen-yl)imidazol-2-yl-idene ligand in a distorted trigonal-planar geometry. The two symmetry-related iodide anions bridge two Li(I) cations, forming an inversion dimer in which the Li2I2 plane is nearly perpendicular to the imidazol-2-yl-idene ring, with a dihedral angle of 85.5 (3)°. No hydrogen bonding is observed in the crystal.

Related literature

For a related lithium complex of imidazol-2-ylidenes, see: Hill et al. (2011 ▸). For related lithium complexes with Li—I bonds, see: Raston et al. (1989 ▸); Fei et al. (2003 ▸); Thatcher et al. (2012 ▸). For applications of imidazol-2-ylidenes in catalysis, see: Vougioukalakis & Grubbs (2010 ▸); Fortman & Nolan (2011 ▸); Valente et al. (2012 ▸); Riener et al. (2014 ▸); Wang et al. (2008 ▸); Mahoney et al. (2013 ▸); Kolychev et al. (2013 ▸); Biju et al. (2011 ▸); Berkessel et al. (2012 ▸); Fèvre et al. (2013 ▸).

Experimental

Crystal data

[Li2(C27H36N2)2I2]

M = 1044.84

Monoclinic,

a = 10.645 (4) Å

b = 14.490 (6) Å

c = 19.217 (7) Å

β = 105.565 (6)°

V = 2855.4 (19) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▸) T min = 0.727, T max = 0.805

11711 measured reflections

5069 independent reflections

2924 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.112

S = 1.00

5069 reflections

288 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −1.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009822/xu5851sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009822/xu5851Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015009822/xu5851fig1.tif

The mol­ecular structure of the title compound with the atom-numbering scheme and 30% probability displacement ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S2056989015009822/xu5851fig2.tif

The packing diagram viewed along the a axis.

CCDC reference: 1402139

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Li2(C27H36N2)2I2]	F(000) = 1072
Mr = 1044.84	Dx = 1.215 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3834 reflections
a = 10.645 (4) Å	θ = 2.4–22.6°
b = 14.490 (6) Å	µ = 1.14 mm−1
c = 19.217 (7) Å	T = 293 K
β = 105.565 (6)°	Block, pale-yellow
V = 2855.4 (19) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Bruker APEXII CCD diffractometer	5069 independent reflections
Radiation source: fine-focus sealed tube	2924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.727, Tmax = 0.805	k = −16→17
11711 measured reflections	l = −22→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0129P)2 + 2.6P] where P = (Fo2 + 2Fc2)/3
5069 reflections	(Δ/σ)max = 0.002
288 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −1.23 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
Li1	0.5511 (8)	0.9291 (5)	0.9451 (4)	0.073 (2)
N1	0.5147 (3)	0.7930 (2)	0.81899 (15)	0.0471 (8)
N2	0.7164 (3)	0.8253 (2)	0.85073 (15)	0.0495 (8)
I1	0.45770 (6)	1.10068 (3)	0.918028 (19)	0.1292 (3)
C1	0.6043 (4)	0.8421 (3)	0.86912 (18)	0.0465 (9)
C2	0.5699 (4)	0.7470 (3)	0.7712 (2)	0.0613 (11)
H2	0.5272	0.7092	0.7331	0.074*
C3	0.6961 (5)	0.7677 (3)	0.7908 (2)	0.0614 (12)
H3	0.7589	0.7475	0.7687	0.074*
C4	0.3808 (4)	0.7834 (3)	0.81913 (19)	0.0490 (10)
C5	0.3503 (5)	0.7218 (3)	0.8690 (2)	0.0620 (11)
C6	0.2220 (5)	0.7133 (4)	0.8677 (3)	0.0815 (15)
H6	0.1990	0.6744	0.9008	0.098*
C7	0.1267 (5)	0.7603 (4)	0.8191 (3)	0.0898 (17)
H7	0.0398	0.7519	0.8185	0.108*
C8	0.1584 (5)	0.8200 (3)	0.7711 (3)	0.0780 (14)
H8	0.0924	0.8520	0.7385	0.094*
C9	0.2867 (4)	0.8334 (3)	0.7702 (2)	0.0587 (11)
C10	0.4551 (5)	0.6667 (4)	0.9205 (3)	0.0937 (17)
H10	0.5353	0.7035	0.9313	0.112*
C11	0.4827 (7)	0.5777 (5)	0.8879 (4)	0.148 (3)
H11A	0.5586	0.5493	0.9192	0.222*
H11B	0.4980	0.5896	0.8417	0.222*
H11C	0.4093	0.5371	0.8820	0.222*
C12	0.4245 (8)	0.6461 (5)	0.9924 (3)	0.153 (3)
H12A	0.5024	0.6257	1.0271	0.229*
H12B	0.3594	0.5987	0.9854	0.229*
H12C	0.3927	0.7010	1.0098	0.229*
C13	0.3189 (5)	0.9005 (3)	0.7174 (2)	0.0703 (13)
H13	0.4135	0.9100	0.7314	0.084*
C14	0.2809 (7)	0.8614 (5)	0.6418 (3)	0.127 (2)
H14A	0.2993	0.9059	0.6089	0.190*
H14B	0.1894	0.8474	0.6282	0.190*
H14C	0.3298	0.8061	0.6404	0.190*
C15	0.2544 (6)	0.9935 (4)	0.7182 (3)	0.112 (2)
H15A	0.2695	1.0144	0.7671	0.168*
H15B	0.1623	0.9878	0.6966	0.168*
H15C	0.2904	1.0372	0.6912	0.168*
C16	0.8436 (4)	0.8581 (3)	0.8895 (2)	0.0534 (10)
C17	0.8907 (4)	0.9376 (3)	0.8648 (2)	0.0611 (11)
C18	1.0158 (5)	0.9638 (3)	0.9004 (3)	0.0814 (14)
H18	1.0511	1.0160	0.8847	0.098*
C19	1.0898 (5)	0.9153 (4)	0.9582 (3)	0.0869 (16)
H19	1.1738	0.9348	0.9816	0.104*
C20	1.0385 (5)	0.8372 (4)	0.9814 (3)	0.0823 (15)
H20	1.0892	0.8043	1.0205	0.099*
C21	0.9143 (4)	0.8066 (3)	0.9482 (2)	0.0645 (12)
C22	0.8123 (5)	0.9924 (3)	0.8010 (2)	0.0720 (13)
H22	0.7264	0.9631	0.7854	0.086*
C23	0.8713 (6)	0.9880 (5)	0.7376 (3)	0.135 (3)
H23A	0.8821	0.9247	0.7258	0.202*
H23B	0.9546	1.0182	0.7502	0.202*
H23C	0.8144	1.0183	0.6967	0.202*
C24	0.7897 (6)	1.0907 (3)	0.8207 (3)	0.1030 (18)
H24A	0.8717	1.1226	0.8353	0.155*
H24B	0.7493	1.0909	0.8598	0.155*
H24C	0.7338	1.1212	0.7796	0.155*
C25	0.8619 (5)	0.7196 (4)	0.9735 (3)	0.0839 (15)
H25	0.7715	0.7119	0.9446	0.101*
C26	0.9377 (6)	0.6344 (4)	0.9617 (3)	0.112 (2)
H26A	1.0273	0.6404	0.9888	0.168*
H26B	0.9329	0.6286	0.9113	0.168*
H26C	0.9008	0.5804	0.9775	0.168*
C27	0.8602 (6)	0.7278 (5)	1.0525 (3)	0.134 (3)
H27A	0.8199	0.6740	1.0662	0.200*
H27B	0.8117	0.7817	1.0585	0.200*
H27C	0.9480	0.7329	1.0825	0.200*

	U11	U22	U33	U12	U13	U23
Li1	0.100 (6)	0.067 (5)	0.061 (4)	0.008 (5)	0.038 (4)	−0.015 (4)
N1	0.048 (2)	0.0510 (19)	0.0438 (17)	0.0020 (16)	0.0147 (16)	−0.0048 (15)
N2	0.049 (2)	0.053 (2)	0.0468 (17)	0.0063 (17)	0.0124 (16)	−0.0039 (15)
I1	0.2440 (6)	0.0875 (3)	0.0756 (2)	0.0609 (3)	0.0765 (3)	0.0164 (2)
C1	0.050 (3)	0.047 (2)	0.043 (2)	0.008 (2)	0.0126 (19)	0.0010 (17)
C2	0.064 (3)	0.067 (3)	0.055 (2)	−0.001 (2)	0.021 (2)	−0.019 (2)
C3	0.063 (3)	0.068 (3)	0.059 (3)	0.006 (2)	0.027 (2)	−0.017 (2)
C4	0.047 (3)	0.051 (2)	0.052 (2)	0.000 (2)	0.020 (2)	−0.0083 (18)
C5	0.069 (3)	0.060 (3)	0.064 (3)	0.000 (2)	0.030 (2)	−0.002 (2)
C6	0.090 (4)	0.077 (4)	0.096 (4)	−0.014 (3)	0.057 (3)	−0.003 (3)
C7	0.071 (4)	0.081 (4)	0.137 (5)	−0.004 (3)	0.063 (4)	−0.012 (4)
C8	0.056 (3)	0.071 (3)	0.112 (4)	0.012 (3)	0.030 (3)	0.009 (3)
C9	0.051 (3)	0.056 (3)	0.070 (3)	0.003 (2)	0.018 (2)	−0.006 (2)
C10	0.098 (4)	0.098 (4)	0.087 (3)	−0.014 (4)	0.028 (3)	0.038 (3)
C11	0.175 (7)	0.142 (7)	0.142 (6)	0.093 (6)	0.067 (5)	0.052 (5)
C12	0.254 (9)	0.122 (5)	0.081 (4)	−0.016 (6)	0.044 (5)	0.028 (4)
C13	0.058 (3)	0.069 (3)	0.081 (3)	0.006 (2)	0.012 (2)	0.019 (2)
C14	0.186 (7)	0.124 (5)	0.081 (4)	−0.022 (5)	0.055 (4)	0.001 (4)
C15	0.134 (5)	0.077 (4)	0.128 (5)	0.016 (4)	0.040 (4)	0.030 (4)
C16	0.046 (3)	0.059 (3)	0.054 (2)	0.008 (2)	0.011 (2)	−0.009 (2)
C17	0.053 (3)	0.054 (3)	0.075 (3)	0.005 (2)	0.014 (2)	−0.008 (2)
C18	0.073 (4)	0.064 (3)	0.105 (4)	−0.004 (3)	0.021 (3)	−0.009 (3)
C19	0.059 (3)	0.087 (4)	0.105 (4)	−0.004 (3)	0.005 (3)	−0.027 (3)
C20	0.066 (4)	0.099 (4)	0.069 (3)	0.015 (3)	−0.004 (3)	−0.008 (3)
C21	0.057 (3)	0.070 (3)	0.062 (3)	0.009 (3)	0.007 (2)	−0.004 (2)
C22	0.076 (3)	0.058 (3)	0.084 (3)	0.011 (3)	0.025 (3)	0.009 (2)
C23	0.160 (6)	0.153 (6)	0.105 (4)	0.076 (5)	0.060 (4)	0.036 (4)
C24	0.128 (5)	0.072 (4)	0.111 (4)	0.036 (4)	0.035 (4)	0.014 (3)
C25	0.071 (3)	0.091 (4)	0.081 (3)	0.008 (3)	0.006 (3)	0.028 (3)
C26	0.132 (5)	0.079 (4)	0.123 (5)	0.003 (4)	0.030 (4)	0.004 (3)
C27	0.163 (6)	0.138 (6)	0.122 (5)	0.034 (5)	0.076 (5)	0.044 (4)

Li1—C1	2.120 (7)	C13—H13	0.9800
Li1—I1	2.676 (8)	C14—H14A	0.9600
Li1—I1i	2.691 (7)	C14—H14B	0.9600
Li1—Li1i	3.328 (13)	C14—H14C	0.9600
N1—C1	1.360 (4)	C15—H15A	0.9600
N1—C2	1.386 (5)	C15—H15B	0.9600
N1—C4	1.433 (5)	C15—H15C	0.9600
N2—C1	1.354 (4)	C16—C17	1.389 (6)
N2—C3	1.391 (5)	C16—C21	1.393 (6)
N2—C16	1.440 (5)	C17—C18	1.377 (6)
I1—Li1i	2.691 (7)	C17—C22	1.510 (6)
C2—C3	1.328 (5)	C18—C19	1.371 (6)
C2—H2	0.9300	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.382 (7)
C4—C9	1.382 (5)	C19—H19	0.9300
C4—C5	1.410 (5)	C20—C21	1.378 (6)
C5—C6	1.365 (6)	C20—H20	0.9300
C5—C10	1.507 (6)	C21—C25	1.512 (6)
C6—C7	1.363 (6)	C22—C24	1.509 (6)
C6—H6	0.9300	C22—C23	1.514 (7)
C7—C8	1.371 (7)	C22—H22	0.9800
C7—H7	0.9300	C23—H23A	0.9600
C8—C9	1.384 (6)	C23—H23B	0.9600
C8—H8	0.9300	C23—H23C	0.9600
C9—C13	1.510 (6)	C24—H24A	0.9600
C10—C11	1.497 (8)	C24—H24B	0.9600
C10—C12	1.531 (7)	C24—H24C	0.9600
C10—H10	0.9800	C25—C26	1.525 (7)
C11—H11A	0.9600	C25—C27	1.527 (7)
C11—H11B	0.9600	C25—H25	0.9800
C11—H11C	0.9600	C26—H26A	0.9600
C12—H12A	0.9600	C26—H26B	0.9600
C12—H12B	0.9600	C26—H26C	0.9600
C12—H12C	0.9600	C27—H27A	0.9600
C13—C14	1.509 (7)	C27—H27B	0.9600
C13—C15	1.514 (7)	C27—H27C	0.9600
C1—Li1—I1	124.9 (3)	C13—C14—H14B	109.5
C1—Li1—I1i	131.6 (4)	H14A—C14—H14B	109.5
I1—Li1—I1i	103.4 (2)	C13—C14—H14C	109.5
C1—Li1—Li1i	175.8 (5)	H14A—C14—H14C	109.5
I1—Li1—Li1i	51.9 (2)	H14B—C14—H14C	109.5
I1i—Li1—Li1i	51.48 (18)	C13—C15—H15A	109.5
C1—N1—C2	112.3 (3)	C13—C15—H15B	109.5
C1—N1—C4	123.9 (3)	H15A—C15—H15B	109.5
C2—N1—C4	123.6 (3)	C13—C15—H15C	109.5
C1—N2—C3	111.8 (3)	H15A—C15—H15C	109.5
C1—N2—C16	125.3 (3)	H15B—C15—H15C	109.5
C3—N2—C16	122.8 (3)	C17—C16—C21	123.7 (4)
Li1—I1—Li1i	76.6 (2)	C17—C16—N2	118.2 (4)
N2—C1—N1	102.8 (3)	C21—C16—N2	118.1 (4)
N2—C1—Li1	134.7 (4)	C18—C17—C16	116.6 (4)
N1—C1—Li1	122.2 (3)	C18—C17—C22	120.5 (4)
C3—C2—N1	106.2 (4)	C16—C17—C22	122.8 (4)
C3—C2—H2	126.9	C19—C18—C17	122.0 (5)
N1—C2—H2	126.9	C19—C18—H18	119.0
C2—C3—N2	106.9 (4)	C17—C18—H18	119.0
C2—C3—H3	126.5	C18—C19—C20	119.4 (5)
N2—C3—H3	126.5	C18—C19—H19	120.3
C9—C4—C5	122.5 (4)	C20—C19—H19	120.3
C9—C4—N1	119.2 (3)	C21—C20—C19	121.8 (5)
C5—C4—N1	118.3 (4)	C21—C20—H20	119.1
C6—C5—C4	117.2 (4)	C19—C20—H20	119.1
C6—C5—C10	121.7 (4)	C20—C21—C16	116.5 (5)
C4—C5—C10	121.1 (4)	C20—C21—C25	120.7 (4)
C7—C6—C5	121.6 (5)	C16—C21—C25	122.8 (4)
C7—C6—H6	119.2	C24—C22—C17	112.6 (4)
C5—C6—H6	119.2	C24—C22—C23	111.7 (5)
C6—C7—C8	120.3 (5)	C17—C22—C23	111.9 (4)
C6—C7—H7	119.8	C24—C22—H22	106.7
C8—C7—H7	119.8	C17—C22—H22	106.7
C7—C8—C9	121.3 (5)	C23—C22—H22	106.7
C7—C8—H8	119.4	C22—C23—H23A	109.5
C9—C8—H8	119.4	C22—C23—H23B	109.5
C4—C9—C8	117.1 (4)	H23A—C23—H23B	109.5
C4—C9—C13	122.8 (4)	C22—C23—H23C	109.5
C8—C9—C13	120.1 (4)	H23A—C23—H23C	109.5
C11—C10—C5	112.0 (5)	H23B—C23—H23C	109.5
C11—C10—C12	108.8 (5)	C22—C24—H24A	109.5
C5—C10—C12	113.4 (5)	C22—C24—H24B	109.5
C11—C10—H10	107.4	H24A—C24—H24B	109.5
C5—C10—H10	107.4	C22—C24—H24C	109.5
C12—C10—H10	107.4	H24A—C24—H24C	109.5
C10—C11—H11A	109.5	H24B—C24—H24C	109.5
C10—C11—H11B	109.5	C21—C25—C26	111.8 (4)
H11A—C11—H11B	109.5	C21—C25—C27	111.0 (5)
C10—C11—H11C	109.5	C26—C25—C27	111.1 (5)
H11A—C11—H11C	109.5	C21—C25—H25	107.6
H11B—C11—H11C	109.5	C26—C25—H25	107.6
C10—C12—H12A	109.5	C27—C25—H25	107.6
C10—C12—H12B	109.5	C25—C26—H26A	109.5
H12A—C12—H12B	109.5	C25—C26—H26B	109.5
C10—C12—H12C	109.5	H26A—C26—H26B	109.5
H12A—C12—H12C	109.5	C25—C26—H26C	109.5
H12B—C12—H12C	109.5	H26A—C26—H26C	109.5
C14—C13—C9	110.7 (4)	H26B—C26—H26C	109.5
C14—C13—C15	109.8 (4)	C25—C27—H27A	109.5
C9—C13—C15	112.4 (4)	C25—C27—H27B	109.5
C14—C13—H13	107.9	H27A—C27—H27B	109.5
C9—C13—H13	107.9	C25—C27—H27C	109.5
C15—C13—H13	107.9	H27A—C27—H27C	109.5
C13—C14—H14A	109.5	H27B—C27—H27C	109.5

Table 1

Selected bond lengths ()

Li1C1	2.120(7)
Li1I1	2.676(8)
Li1I1i	2.691(7)

Symmetry code: (i) .