Crystal structure of di-μ-iodido-bis­{[1,3-bis­(2,6-diiso­propyl­phen­yl)imidazol-2-yl­idene]lithium}

Wan, H.-D.; Hong, J.-Q.

doi:10.1107/S2056989015009822

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages m137-m138

doi:10.1107/S2056989015009822

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Crystal structure of di-μ-iodido-bis{[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]lithium}

Hui-Da Wan ^a and Jian-Quan Hong ^a ^*

^aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
^*Correspondence e-mail: hongjq@jiangnan.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 9 May 2015; accepted 21 May 2015; online 28 May 2015)

In the title binuclear complex, [Li₂(C₂₇H₃₆N₂)₂I₂], the unique Li^I cation is coordinated by two iodide anions and one ylidene C atom from a 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 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-ylidene ring, with a dihedral angle of 85.5 (3)°. No hydrogen bonding is observed in the crystal.

Keywords: crystal structure; dinuclear lithium complex; imidazol-2-ylidene ligand; catalysis.

CCDC reference: 1402139

1. 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 ).

2. Experimental

2.1. Crystal data

[Li₂(C₂₇H₃₆N₂)₂I₂]
M_r = 1044.84
Monoclinic, P 2₁ /c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.112
S = 1.00
5069 reflections
288 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Li1—C1	2.120 (7)
Li1—I1	2.676 (8)
Li1—I1ⁱ	2.691 (7)
Symmetry code: (i) -x+1, -y+2, -z+2.

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.

Supporting information

CCDC reference: 1402139

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009822/xu5851sup1.cif

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

checkCIF report

Comment top

Imidazol-2-ylidenes (NHCs), are excellent σ-donors and readily coordinate to transition metals and p-block elements. This feature has led to the most important application of NHCs as ancillary ligands in homogeneous transition-metal catalysis (Vougioukalakis et al., 2010; Fortman et al., 2011; Valente et al., 2012; Riener et al., 2014) and p-block elements (Wang et al., 2008; Mahoney et al., 2013; Kolychev et al., 2013). NHCs have enabled the preparation and characterization of previously unknown species featuring p-block species in unconventional forms, such as in the zero-oxidation state or as radicals. As organocatalysts, NHCs can also promote a wide range of different organic transformations, with most processes involving an initial attack of the NHC onto a carbonyl group (Biju et al., 2011; Berkessel et al., 2012; Fèvre et al., 2013).

Single-crystal X-ray diffraction analyses the title compound reveals that Li is tri-coordinate. As shown in Fig. 1, the moiety of the dimer contains one Li atom, a NHC ligand and one iodine atom. The dative Li← C bond distance is 2.120 (7) Å, whic is slightly shorter than those of NHC species [M(IPr)₂]⁺[M'{N(SiMe₃)₂}₃]^- (M = Li, Na, K; M' = Mg, Ca, Sr, Ba). (Hill et al., 2011) The Li—I bond distances are in the range of 2.676 (8)–2.691 (7) Å, which are remarkably shorter than the values in lithium complexes (2.767 (16)–2.932 (6) Å) with µ-bridging iodine constructions. (Raston et al., 1989; Fei et al., 2003; Thatcher et al., 2012). Fig. 2 shows the molecular packing of the title compound, viewed along the a axis.

Related literature top

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 et al. (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 top

A flame-dried Schlenk tube under a nitrogen atmosphere was charged with 1,3-Bis(2,6-diisopropylphenyl)imidazolinium iodide (0.516 g, 1mmol) and THF (10mL) at -78°C. To this was added a THF solution of lithium hexamethyldisilazide (0.167 g, 1 mmol). The mixture was allowed to slowly warm to room temperature and was stirred for 3 h. All volatiles were removed under vacuum. The resulting pale-yellow material was washed with cold hexane quickly, and then dried up. 0.376 g (72 %) of [Li(I)(C₂₇H₃₆N₂)]₂ was obtained. Crystals suitable for X-ray analysis were obtained by recrystallization in THF/hexane at -30 °C. Elemental analysis (%) calcd. for Li₂C₅₄H₇₂N₄I₂: C 62.07, H 6.94, N 5.36. Found: C 62.45, H 6.80, N 5.48.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram viewed along the a axis.

Di-µ-iodido-bis{[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]lithium} top

Crystal data top

[Li₂(C₂₇H₃₆N₂)₂I₂]	F(000) = 1072
M_r = 1044.84	D_x = 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

Data collection top

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

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0129P)² + 2.6P] where P = (F_o² + 2F_c²)/3
5069 reflections	(Δ/σ)_max = 0.002
288 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −1.23 e Å⁻³

Crystal data top

[Li₂(C₂₇H₃₆N₂)₂I₂]	V = 2855.4 (19) Å³
M_r = 1044.84	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.645 (4) Å	µ = 1.14 mm⁻¹
b = 14.490 (6) Å	T = 293 K
c = 19.217 (7) Å	0.30 × 0.25 × 0.20 mm
β = 105.565 (6)°

Data collection top

Bruker APEXII CCD diffractometer	5069 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2924 reflections with I > 2σ(I)
T_min = 0.727, T_max = 0.805	R_int = 0.085
11711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.00	Δρ_max = 0.74 e Å⁻³
5069 reflections	Δρ_min = −1.23 e Å⁻³
288 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x+1, −y+2, −z+2.

Selected bond lengths (Å) top

Li1—C1	2.120 (7)	Li1—I1ⁱ	2.691 (7)
Li1—I1	2.676 (8)

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

The diffraction data was collected at Fudan University, China.

References

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Volume 71| Part 6| June 2015| Pages m137-m138

doi:10.1107/S2056989015009822

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

Crystal structure of di-μ-iodido-bis­­{[1,3-bis­­(2,6-diiso­propyl­phen­yl)imidazol-2-yl­­idene]lithium}

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of di-μ-iodido-bis{[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]lithium}