Crystal structure of tris­(1,3-dimesityl-4,5-di­hydro-1H-imidazol-3-ium) tetra­bromido­cobaltate(II) bromide chloro­form hexa­solvate

Rais, E.; Flörke, U.; Wilhelm, R.

doi:10.1107/S2056989015016254

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages m177-m178

doi:10.1107/S2056989015016254

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Crystal structure of tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) tetrabromidocobaltate(II) bromide chloroform hexasolvate

Eduard Rais,^a Ulrich Flörke ^a ^* and René Wilhelm ^a ^*

^aDepartment Chemie, Universität Paderborn, Warburgerstrasse 100, 33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de, rene.wilhelm@upb.de

Edited by M. Nieger, University of Helsinki, Finland (Received 13 August 2015; accepted 31 August 2015; online 12 September 2015)

In the unit cell of the title compound, (C₂₁H₂₇N₂)₃[CoBr₄]Br·6CHCl₃, the tetrabromidocobaltate(II) anion and the bromide anion are located on a crystallographic threefold rotation axis. For the [CoBr₄]²⁻ group, the axis runs through one of the Br ligands and the Co^II atom. All other structure moieties lie on general sites. Various tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) structures with different counter-ions have been reported. In the title compound, the N—C—N angle is 113.7 (5)°, with short C—N bond lengths of 1.297 (7) and 1.307 (7) Å. The two mesityl planes make a dihedral angle of 34.6 (1)° and the dihedral angles between the mesityl and N–C–N planes are 82.0 (1) and 88.5 (1)°, respectively. The imidazoline ring is almost planar, with atom deviations in the range 0.003 (5)–0.017 (5) Å from the best plane; the mean deviation is 0.012 (5) Å. In the crystal, non-covalent interactions of the C—H⋯Br type occur between the Br⁻ anion and the cation, as well as between the [CoBr₄]²⁻ anion and both the chloroform solvent molecules. These H⋯A distances are slightly shorter than the sum of van der Waals radii.

Keywords: crystal structure; imidazolium salt; absolute structure; C—H⋯Br interactions.

CCDC reference: 1421420

1. Related literature

For similar tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) structures, see: Arduengo et al. (1995 ); Hagos et al. (2008 ); Santoro et al. (2013 ); Buchalski et al. (2015 ). For synthesis of 2-bromo-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium bromide, see: Wiggins et al. (2012 ). For the application of 1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium cation as a carbene precursor, see: Díez-González et al. (2009 ). For catalytic application of imidazolium based [CoCl₄]²⁻ salts, see: Bica & Gärtner (2008 ); Wang et al. (2015 ).

2. Experimental

2.1. Crystal data

(C₂₁H₂₇N₂)₃[CoBr₄]Br·6CHCl₃
M_r = 2097.02
Trigonal, R 3c :H
a = 16.0535 (14) Å
c = 61.790 (12) Å
V = 13791 (4) Å³
Z = 6
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 130 K
0.22 × 0.21 × 0.20 mm

2.2. Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.279, T_max = 1.0
41734 measured reflections
7309 independent reflections
4427 reflections with I > 2σ(I)
R_int = 0.077

2.3. Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.078
S = 0.79
7309 reflections
306 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.65 e Å⁻³
Absolute structure: Flack (1983 ), 1821 Friedel pairs
Absolute structure parameter: 0.020 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Br3ⁱⁱ	0.95	2.58	3.373 (4)	141
C100—H10⋯Br1ⁱ	1.00	2.71	3.668 (5)	161
C200—H20⋯Br2ⁱⁱⁱ	1.00	2.54	3.454 (6)	152
Symmetry codes: (i) -x+y+1, -x+1, z; (ii) x, y-1, z; (iii) $[-y+{\script{1\over 3}}, -x+{\script{5\over 3}}, z-{\script{5\over 6}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

CCDC reference: 1421420

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015016254/nr2061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016254/nr2061Isup2.hkl

checkCIF report

Synthesis and crystallization top

All manipulations were carried out under nitrogen atmosphere using standard Schlenk techniques. MeCN was dried with an MBRAUN MB SPS-800 solvent purification system under nitrogen. CHCl₃ was dried over activated molecular sieve with 3 Å pore diameter. 2-Bromo-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium bromide (0.080 g, 0.172 mmol, 1 eq) and Cobalt powder (0.227 g, 3.852 mmol, 22 eq, grain size < 150 µm) were filled into a sealed schlenk tube equipped with a stirring bar. MeCN (3 mL) was added and the mixture was stirred and heated at 100 °C for 40 h under inert gas. The cooled down mixture was filtrated and the solvent was then removed under vacuum. The residual brown oil was separated by decantation and was dissolved in CHCl₃ (0.7 mL). Crystal growth could be observed after one day. The NMR spectra are not suitable because of the paramagnetic properties of the [CoBr₄]^2- anion.

Refinement top

Hydrogen atom positions were clearly derived from difference Fourier maps and then refined at idealized positions riding on the carbon atoms with isotropic displacement parameters U_iso(H) = 1.2U(C_eq) or 1.5U(-CH₃) and C–H 0.95-1.00 Å. All CH₃ hydrogen atoms were allowed to rotate but not to tip. It was not possible to refine a satisfactory split model for the C100–chloroform.

Chemical Context top

The cation is a common precursor for the synthesis of 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene, which is used as a ligand in various catalytic applications (Díez-González et al., 2009). Alkyl-substituted imidazolium cations with [CoX₄]^2- anions (X = Cl, Br) are used as metal-containing ionic liquids (Bica & Gaertner, 2008; Wang et al., 2015).

Related literature top

For similar tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) structures, see: Arduengo et al. (1995); Hagos et al. (2008); Santoro et al. (2013); Buchalski et al. (2015). For synthesis of 2-bromo-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium bromide, see: Wiggins et al. (2012). For the application of 1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium cation as a carbene precursor, see: Díez-González et al. (2009). For catalytic application of imidazolium based [CoCl₄]^2- salts, see: Bica & Gaertner (2008); Wang et al. (2015).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and local programs.

Figures top

	Fig. 1. Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level. Non-stoichiometric representation.
	Fig. 2. Crystal packing approximately viewed along a axis with intermolecular hydrogen bonding pattern drawn as dotted lines. H-atoms not involved are omitted.

Tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) tetrabromidocobaltate(II) bromide chloroform hexasolvate top

Crystal data top

(C₂₁H₂₇N₂)₃[CoBr₄]Br·6CHCl₃	D_x = 1.515 Mg m⁻³
M_r = 2097.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c:H	Cell parameters from 4234 reflections
a = 16.0535 (14) Å	θ = 2.5–19.7°
c = 61.790 (12) Å	µ = 2.92 mm⁻¹
V = 13791 (4) Å³	T = 130 K
Z = 6	Prism, pale-green
F(000) = 6306	0.22 × 0.21 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	7309 independent reflections
Radiation source: sealed tube	4427 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
φ and ω scans	θ_max = 27.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −21→21
T_min = 0.279, T_max = 1.0	k = −21→19
41734 measured reflections	l = −81→81

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0298P)²] where P = (F_o² + 2F_c²)/3
S = 0.79	(Δ/σ)_max = 0.001
7309 reflections	Δρ_max = 0.65 e Å⁻³
306 parameters	Δρ_min = −0.64 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1821 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (11)

Crystal data top

(C₂₁H₂₇N₂)₃[CoBr₄]Br·6CHCl₃	Z = 6
M_r = 2097.02	Mo Kα radiation
Trigonal, R3c:H	µ = 2.92 mm⁻¹
a = 16.0535 (14) Å	T = 130 K
c = 61.790 (12) Å	0.22 × 0.21 × 0.20 mm
V = 13791 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	7309 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4427 reflections with I > 2σ(I)
T_min = 0.279, T_max = 1.0	R_int = 0.077
41734 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.65 e Å⁻³
S = 0.79	Δρ_min = −0.64 e Å⁻³
7309 reflections	Absolute structure: Flack (1983), 1821 Friedel pairs
306 parameters	Absolute structure parameter: 0.020 (11)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
Co1	0.6667	0.3333	0.91225 (2)	0.0290 (3)
Br1	0.77035 (4)	0.49648 (5)	0.92389 (2)	0.04336 (19)
Br2	0.6667	0.3333	0.87362 (2)	0.0630 (4)
Br3	0.3333	0.6667	0.91594 (3)	0.0524 (4)
N1	0.4682 (3)	−0.0461 (3)	0.90279 (8)	0.0296 (12)
N2	0.4612 (3)	−0.0455 (3)	0.93802 (8)	0.0281 (12)
C1	0.4610 (4)	−0.0918 (4)	0.92081 (10)	0.0292 (14)
H1A	0.4561	−0.1533	0.9213	0.035*
C2	0.4754 (4)	0.0476 (4)	0.90750 (10)	0.0338 (16)
H2A	0.4225	0.0526	0.9005	0.041*
H2B	0.5378	0.1017	0.9026	0.041*
C3	0.4669 (4)	0.0462 (4)	0.93224 (9)	0.0270 (14)
H3A	0.5239	0.1015	0.9389	0.032*
H3B	0.4082	0.0472	0.9368	0.032*
C4	0.4725 (4)	−0.0782 (4)	0.88091 (10)	0.0319 (15)
C5	0.5614 (5)	−0.0511 (5)	0.87196 (13)	0.049 (2)
C6	0.5625 (6)	−0.0800 (5)	0.85046 (12)	0.055 (2)
H6A	0.6222	−0.0621	0.8437	0.065*
C7	0.4769 (7)	−0.1346 (6)	0.83901 (12)	0.054 (2)
C8	0.3921 (6)	−0.1592 (5)	0.84898 (11)	0.0464 (18)
H8A	0.3340	−0.1964	0.8412	0.056*
C9	0.3867 (5)	−0.1327 (4)	0.86980 (11)	0.0375 (16)
C10	0.6534 (5)	0.0048 (6)	0.88517 (16)	0.087 (3)
H10A	0.6525	−0.0346	0.8974	0.130*
H10B	0.6577	0.0641	0.8907	0.130*
H10C	0.7092	0.0210	0.8760	0.130*
C11	0.4845 (7)	−0.1602 (6)	0.81586 (12)	0.080 (3)
H11A	0.5414	−0.1673	0.8143	0.120*
H11B	0.4902	−0.1090	0.8062	0.120*
H11C	0.4268	−0.2209	0.8120	0.120*
C12	0.2910 (5)	−0.1610 (5)	0.87956 (12)	0.0503 (19)
H12A	0.2405	−0.1947	0.8687	0.075*
H12B	0.2902	−0.1032	0.8844	0.075*
H12C	0.2795	−0.2035	0.8919	0.075*
C13	0.4495 (4)	−0.0797 (4)	0.96013 (10)	0.0293 (14)
C14	0.5308 (4)	−0.0439 (4)	0.97348 (11)	0.0356 (16)
C15	0.5164 (5)	−0.0718 (4)	0.99472 (11)	0.0395 (17)
H15A	0.5707	−0.0479	1.0040	0.047*
C16	0.4255 (5)	−0.1339 (4)	1.00332 (11)	0.0403 (17)
C17	0.3468 (5)	−0.1667 (5)	0.98966 (12)	0.0454 (19)
H17A	0.2845	−0.2091	0.9953	0.055*
C18	0.3559 (5)	−0.1394 (4)	0.96770 (12)	0.0378 (16)
C19	0.6300 (4)	0.0195 (5)	0.96462 (11)	0.0487 (19)
H19A	0.6332	0.0760	0.9577	0.073*
H19B	0.6447	−0.0163	0.9539	0.073*
H19C	0.6769	0.0403	0.9764	0.073*
C20	0.4143 (6)	−0.1603 (5)	1.02691 (12)	0.059 (2)
H20A	0.4242	−0.2153	1.0290	0.089*
H20B	0.3495	−0.1774	1.0317	0.089*
H20C	0.4620	−0.1054	1.0354	0.089*
C21	0.2699 (4)	−0.1763 (5)	0.95317 (12)	0.0503 (19)
H21A	0.2725	−0.2195	0.9423	0.076*
H21B	0.2698	−0.1221	0.9459	0.076*
H21C	0.2111	−0.2116	0.9618	0.076*
C100	0.8893 (6)	0.1327 (6)	0.92865 (13)	0.070 (3)
H10	0.8362	0.1455	0.9248	0.084*
Cl11	0.91290 (19)	0.1546 (2)	0.95548 (4)	0.0938 (8)
Cl12	0.8521 (2)	0.0149 (2)	0.92250 (7)	0.1562 (18)
Cl13	0.9911 (3)	0.2121 (2)	0.91398 (5)	0.1293 (12)
C200	0.0704 (6)	0.8507 (6)	0.01629 (18)	0.091 (3)
H20	0.0749	0.9066	0.0245	0.109*
Cl21	0.1365 (2)	0.8900 (2)	−0.00698 (6)	0.1410 (14)
Cl22	0.11836 (19)	0.7912 (2)	0.03238 (5)	0.1032 (9)
Cl23	−0.05036 (16)	0.76626 (15)	0.01124 (4)	0.0790 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0214 (5)	0.0214 (5)	0.0440 (10)	0.0107 (2)	0.000	0.000
Br1	0.0253 (3)	0.0267 (3)	0.0769 (5)	0.0121 (3)	−0.0062 (4)	−0.0129 (3)
Br2	0.0687 (6)	0.0687 (6)	0.0515 (9)	0.0344 (3)	0.000	0.000
Br3	0.0263 (4)	0.0263 (4)	0.1045 (11)	0.01314 (19)	0.000	0.000
N1	0.030 (3)	0.027 (3)	0.033 (3)	0.015 (2)	−0.001 (2)	−0.004 (2)
N2	0.032 (3)	0.026 (3)	0.028 (3)	0.016 (2)	0.003 (2)	0.000 (2)
C1	0.023 (3)	0.024 (3)	0.034 (4)	0.007 (3)	0.002 (3)	0.002 (3)
C2	0.032 (4)	0.025 (3)	0.046 (5)	0.015 (3)	−0.004 (3)	−0.004 (3)
C3	0.031 (3)	0.027 (3)	0.027 (4)	0.017 (3)	−0.001 (3)	−0.005 (3)
C4	0.041 (4)	0.024 (3)	0.031 (4)	0.016 (3)	0.004 (3)	0.004 (3)
C5	0.051 (5)	0.034 (4)	0.065 (6)	0.023 (4)	0.013 (4)	−0.001 (4)
C6	0.072 (6)	0.049 (5)	0.056 (6)	0.041 (4)	0.036 (5)	0.017 (4)
C7	0.092 (6)	0.056 (5)	0.037 (5)	0.055 (5)	−0.005 (5)	−0.002 (4)
C8	0.062 (5)	0.056 (5)	0.029 (4)	0.034 (4)	−0.001 (4)	−0.007 (4)
C9	0.052 (4)	0.032 (4)	0.031 (4)	0.023 (3)	−0.005 (3)	−0.003 (3)
C10	0.029 (4)	0.098 (7)	0.125 (9)	0.026 (5)	0.007 (5)	−0.044 (6)
C11	0.149 (9)	0.094 (7)	0.044 (6)	0.095 (7)	0.010 (5)	0.005 (5)
C12	0.043 (4)	0.047 (4)	0.050 (5)	0.014 (4)	−0.009 (4)	−0.015 (4)
C13	0.037 (4)	0.020 (3)	0.032 (4)	0.015 (3)	0.004 (3)	0.002 (3)
C14	0.039 (4)	0.027 (3)	0.039 (5)	0.015 (3)	0.001 (3)	0.010 (3)
C15	0.047 (4)	0.040 (4)	0.035 (5)	0.024 (4)	0.000 (3)	0.007 (3)
C16	0.060 (5)	0.034 (4)	0.034 (4)	0.030 (4)	0.005 (4)	0.004 (3)
C17	0.052 (5)	0.036 (4)	0.045 (5)	0.021 (4)	0.028 (4)	0.011 (4)
C18	0.041 (4)	0.027 (4)	0.046 (5)	0.017 (3)	0.005 (3)	−0.005 (3)
C19	0.034 (4)	0.050 (4)	0.050 (5)	0.012 (4)	−0.001 (3)	0.007 (4)
C20	0.073 (6)	0.052 (5)	0.052 (5)	0.030 (4)	0.019 (4)	0.021 (4)
C21	0.035 (4)	0.050 (4)	0.058 (5)	0.015 (4)	0.011 (4)	0.000 (4)
C100	0.076 (6)	0.086 (6)	0.074 (7)	0.061 (6)	−0.032 (5)	−0.030 (5)
Cl11	0.106 (2)	0.119 (2)	0.0673 (17)	0.0651 (18)	−0.0027 (14)	0.0048 (15)
Cl12	0.159 (3)	0.107 (2)	0.248 (5)	0.101 (2)	−0.115 (3)	−0.096 (3)
Cl13	0.192 (3)	0.165 (3)	0.115 (2)	0.153 (3)	0.073 (2)	0.067 (2)
C200	0.061 (6)	0.049 (5)	0.147 (10)	0.016 (5)	0.028 (6)	−0.021 (6)
Cl21	0.128 (3)	0.114 (2)	0.181 (4)	0.060 (2)	0.098 (3)	0.067 (2)
Cl22	0.096 (2)	0.0933 (19)	0.107 (2)	0.0379 (16)	−0.0029 (17)	−0.0331 (17)
Cl23	0.0694 (15)	0.0597 (14)	0.0825 (17)	0.0131 (12)	0.0122 (13)	−0.0093 (12)

Geometric parameters (Å, º) top

Co1—Br2	2.387 (2)	C11—H11C	0.9800
Co1—Br1	2.4057 (8)	C12—H12A	0.9800
Co1—Br1ⁱ	2.4057 (8)	C12—H12B	0.9800
Co1—Br1ⁱⁱ	2.4057 (8)	C12—H12C	0.9800
N1—C1	1.307 (7)	C13—C18	1.397 (8)
N1—C4	1.460 (7)	C13—C14	1.402 (8)
N1—C2	1.479 (7)	C14—C15	1.368 (8)
N2—C1	1.297 (7)	C14—C19	1.500 (8)
N2—C13	1.449 (7)	C15—C16	1.397 (9)
N2—C3	1.472 (7)	C15—H15A	0.9500
C1—H1A	0.9500	C16—C17	1.386 (10)
C2—C3	1.534 (8)	C16—C20	1.504 (9)
C2—H2A	0.9900	C17—C18	1.411 (9)
C2—H2B	0.9900	C17—H17A	0.9500
C3—H3A	0.9900	C18—C21	1.499 (9)
C3—H3B	0.9900	C19—H19A	0.9800
C4—C5	1.383 (9)	C19—H19B	0.9800
C4—C9	1.389 (8)	C19—H19C	0.9800
C5—C6	1.410 (10)	C20—H20A	0.9800
C5—C10	1.525 (10)	C20—H20B	0.9800
C6—C7	1.397 (10)	C20—H20C	0.9800
C6—H6A	0.9500	C21—H21A	0.9800
C7—C8	1.360 (10)	C21—H21B	0.9800
C7—C11	1.510 (10)	C21—H21C	0.9800
C8—C9	1.371 (9)	C100—Cl11	1.698 (8)
C8—H8A	0.9500	C100—Cl12	1.716 (8)
C9—C12	1.494 (9)	C100—Cl13	1.741 (9)
C10—H10A	0.9800	C100—H10	1.0000
C10—H10B	0.9800	C200—Cl21	1.709 (10)
C10—H10C	0.9800	C200—Cl23	1.751 (9)
C11—H11A	0.9800	C200—Cl22	1.797 (11)
C11—H11B	0.9800	C200—H20	1.0000

Br2—Co1—Br1	107.39 (4)	H11B—C11—H11C	109.5
Br2—Co1—Br1ⁱ	107.39 (4)	C9—C12—H12A	109.5
Br1—Co1—Br1ⁱ	111.47 (4)	C9—C12—H12B	109.5
Br2—Co1—Br1ⁱⁱ	107.39 (4)	H12A—C12—H12B	109.5
Br1—Co1—Br1ⁱⁱ	111.47 (4)	C9—C12—H12C	109.5
Br1ⁱ—Co1—Br1ⁱⁱ	111.47 (4)	H12A—C12—H12C	109.5
C1—N1—C4	126.6 (5)	H12B—C12—H12C	109.5
C1—N1—C2	110.1 (5)	C18—C13—C14	123.0 (6)
C4—N1—C2	123.2 (5)	C18—C13—N2	117.9 (5)
C1—N2—C13	126.4 (5)	C14—C13—N2	118.8 (5)
C1—N2—C3	110.8 (5)	C15—C14—C13	117.4 (6)
C13—N2—C3	122.6 (5)	C15—C14—C19	121.4 (6)
N2—C1—N1	113.7 (5)	C13—C14—C19	121.2 (6)
N2—C1—H1A	123.1	C14—C15—C16	123.0 (6)
N1—C1—H1A	123.1	C14—C15—H15A	118.5
N1—C2—C3	102.7 (5)	C16—C15—H15A	118.5
N1—C2—H2A	111.2	C17—C16—C15	117.9 (6)
C3—C2—H2A	111.2	C17—C16—C20	121.7 (6)
N1—C2—H2B	111.2	C15—C16—C20	120.3 (7)
C3—C2—H2B	111.2	C16—C17—C18	122.3 (6)
H2A—C2—H2B	109.1	C16—C17—H17A	118.9
N2—C3—C2	102.5 (4)	C18—C17—H17A	118.9
N2—C3—H3A	111.3	C13—C18—C17	116.4 (6)
C2—C3—H3A	111.3	C13—C18—C21	122.2 (6)
N2—C3—H3B	111.3	C17—C18—C21	121.4 (6)
C2—C3—H3B	111.3	C14—C19—H19A	109.5
H3A—C3—H3B	109.2	C14—C19—H19B	109.5
C5—C4—C9	122.9 (6)	H19A—C19—H19B	109.5
C5—C4—N1	118.9 (6)	C14—C19—H19C	109.5
C9—C4—N1	118.2 (5)	H19A—C19—H19C	109.5
C4—C5—C6	117.0 (7)	H19B—C19—H19C	109.5
C4—C5—C10	121.0 (7)	C16—C20—H20A	109.5
C6—C5—C10	122.0 (7)	C16—C20—H20B	109.5
C7—C6—C5	120.9 (7)	H20A—C20—H20B	109.5
C7—C6—H6A	119.5	C16—C20—H20C	109.5
C5—C6—H6A	119.5	H20A—C20—H20C	109.5
C8—C7—C6	118.7 (7)	H20B—C20—H20C	109.5
C8—C7—C11	123.7 (8)	C18—C21—H21A	109.5
C6—C7—C11	117.5 (8)	C18—C21—H21B	109.5
C7—C8—C9	123.0 (7)	H21A—C21—H21B	109.5
C7—C8—H8A	118.5	C18—C21—H21C	109.5
C9—C8—H8A	118.5	H21A—C21—H21C	109.5
C8—C9—C4	117.6 (6)	H21B—C21—H21C	109.5
C8—C9—C12	119.9 (6)	Cl11—C100—Cl12	111.3 (5)
C4—C9—C12	122.5 (6)	Cl11—C100—Cl13	109.0 (5)
C5—C10—H10A	109.5	Cl12—C100—Cl13	112.0 (5)
C5—C10—H10B	109.5	Cl11—C100—H10	108.1
H10A—C10—H10B	109.5	Cl12—C100—H10	108.1
C5—C10—H10C	109.5	Cl13—C100—H10	108.1
H10A—C10—H10C	109.5	Cl21—C200—Cl23	112.2 (6)
H10B—C10—H10C	109.5	Cl21—C200—Cl22	108.1 (5)
C7—C11—H11A	109.5	Cl23—C200—Cl22	106.8 (5)
C7—C11—H11B	109.5	Cl21—C200—H20	109.9
H11A—C11—H11B	109.5	Cl23—C200—H20	109.9
C7—C11—H11C	109.5	Cl22—C200—H20	109.9
H11A—C11—H11C	109.5

C13—N2—C1—N1	176.7 (5)	C5—C4—C9—C8	−0.7 (9)
C3—N2—C1—N1	1.7 (7)	N1—C4—C9—C8	177.6 (5)
C4—N1—C1—N2	178.3 (5)	C5—C4—C9—C12	−179.5 (6)
C2—N1—C1—N2	0.4 (7)	N1—C4—C9—C12	−1.2 (9)
C1—N1—C2—C3	−2.2 (6)	C1—N2—C13—C18	−82.7 (7)
C4—N1—C2—C3	179.9 (5)	C3—N2—C13—C18	91.8 (7)
C1—N2—C3—C2	−2.9 (6)	C1—N2—C13—C14	103.6 (7)
C13—N2—C3—C2	−178.1 (5)	C3—N2—C13—C14	−81.9 (7)
N1—C2—C3—N2	2.8 (5)	C18—C13—C14—C15	1.8 (9)
C1—N1—C4—C5	−91.4 (7)	N2—C13—C14—C15	175.0 (5)
C2—N1—C4—C5	86.2 (7)	C18—C13—C14—C19	179.6 (6)
C1—N1—C4—C9	90.3 (7)	N2—C13—C14—C19	−7.1 (9)
C2—N1—C4—C9	−92.1 (7)	C13—C14—C15—C16	0.5 (9)
C9—C4—C5—C6	1.1 (9)	C19—C14—C15—C16	−177.3 (6)
N1—C4—C5—C6	−177.2 (5)	C14—C15—C16—C17	−1.3 (10)
C9—C4—C5—C10	−177.1 (7)	C14—C15—C16—C20	−178.8 (6)
N1—C4—C5—C10	4.6 (10)	C15—C16—C17—C18	−0.1 (9)
C4—C5—C6—C7	−0.8 (10)	C20—C16—C17—C18	177.3 (6)
C10—C5—C6—C7	177.3 (7)	C14—C13—C18—C17	−3.0 (9)
C5—C6—C7—C8	0.3 (10)	N2—C13—C18—C17	−176.4 (5)
C5—C6—C7—C11	178.3 (6)	C14—C13—C18—C21	179.7 (6)
C6—C7—C8—C9	0.1 (11)	N2—C13—C18—C21	6.3 (9)
C11—C7—C8—C9	−177.8 (6)	C16—C17—C18—C13	2.2 (9)
C7—C8—C9—C4	0.1 (10)	C16—C17—C18—C21	179.5 (6)
C7—C8—C9—C12	178.9 (6)

Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br3ⁱⁱⁱ	0.95	2.58	3.373 (4)	141
C100—H10···Br1ⁱ	1.00	2.71	3.668 (5)	161
C200—H20···Br2^iv	1.00	2.54	3.454 (6)	152

Symmetry codes: (i) −x+y+1, −x+1, z; (iii) x, y−1, z; (iv) −y+1/3, −x+5/3, z−5/6.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br3ⁱⁱ	0.95	2.58	3.373 (4)	141.3
C100—H10···Br1ⁱ	1.00	2.71	3.668 (5)	160.7
C200—H20···Br2ⁱⁱⁱ	1.00	2.54	3.454 (6)	151.7

Symmetry codes: (i) −x+y+1, −x+1, z; (ii) x, y−1, z; (iii) −y+1/3, −x+5/3, z−5/6.

References

Arduengo, A. J., Goerlich, J. R. & Marshall, W. J. (1995). J. Am. Chem. Soc. 117, 11027–11028. CrossRef CAS Web of Science Google Scholar
Bica, K. & Gärtner, P. (2008). Eur. J. Org. Chem. 2008, 3453–3456. CrossRef Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buchalski, P., Pacholski, R., Chodkiewicz, K., Buchowicz, W., Suwińska, K. & Shkurenko, A. (2015). Dalton Trans. 44, 7169–7176. CSD CrossRef CAS PubMed Google Scholar
Díez-González, S., Marion, N. & Nolan, S. P. (2009). Chem. Rev. 109, 3612–3676. Web of Science PubMed Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hagos, T. K., Nogai, S. D., Dobrzańska, L. & Cronje, S. (2008). Acta Cryst. E64, m1357. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santoro, O., Collado, A., Slawin, A. M. Z., Nolan, S. P. & Cazin, C. S. J. (2013). Chem. Commun. 49, 10483–10485. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wang, Q., Geng, Y., Lu, X. & Zhang, S. (2015). ACS Sustainable Chem. Eng. 3, 340–348. CrossRef CAS Google Scholar
Wiggins, K. M., Moerdyk, J. P. & Bielawski, C. W. (2012). Chem. Sci. 3, 2986–2992. CSD CrossRef CAS Google Scholar

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Volume 71| Part 10| October 2015| Pages m177-m178

doi:10.1107/S2056989015016254

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

Crystal structure of tris­­(1,3-dimesityl-4,5-di­hydro-1H-imidazol-3-ium) tetra­bromido­cobaltate(II) bromide chloro­form hexa­solvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

metal-organic compounds

Crystal structure of tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) tetrabromidocobaltate(II) bromide chloroform hexasolvate