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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 May 23;68(Pt 6):o1845. doi: 10.1107/S1600536812022246

1,3-Bis(2,6-diisopropyl­phen­yl)-1H-imidazol-3-ium bromide dichloro­methane disolvate

Matthias Berger a, Norbert Auner a, Tanja Sinke a, Michael Bolte a,*
PMCID: PMC3379414  PMID: 22719612

Abstract

In the title compound, C27H37N2 +·Br−·2CH2Cl2, both the cation and the anion are located on a crystallographic mirror plane. Both of the dichloro­methane solvent mol­ecules show a disorder across a mirror plane over two equally occupied positions. In the crystal, the cations are connnected to the bromide ions via C—H⋯Br hydrogen bonds.

Related literature  

For the preparation of imidazolium salts, see: Arduengo et al. (1995 ▶, 1999 ▶); Hinter­mann (2007 ▶). For structures with the same cation but different anions, see: Stasch et al. (2004 ▶); Blue et al. (2006 ▶); Berger et al. (2012 ▶). For compounds with the 1,3-bis-(2,6-diisopropyl­phen­yl)imidazolium unit, see: Ikhile et al. (2010 ▶); Giffin et al. (2010 ▶).graphic file with name e-68-o1845-scheme1.jpg

Experimental  

Crystal data  

  • C27H37N2 +·Br−·2CH2Cl2

  • M r = 639.35

  • Monoclinic, Inline graphic

  • a = 9.1874 (8) Å

  • b = 16.5165 (12) Å

  • c = 11.030 (1) Å

  • β = 102.332 (7)°

  • V = 1635.1 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.60 mm−1

  • T = 173 K

  • 0.52 × 0.28 × 0.24 mm

Data collection  

  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.489, T max = 0.700

  • 20988 measured reflections

  • 3200 independent reflections

  • 2867 reflections with I > 2σ(I)

  • R int = 0.084

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.038

  • wR(F 2) = 0.090

  • S = 1.03

  • 3200 reflections

  • 197 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 .

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022246/ng5272sup1.cif

e-68-o1845-sup1.cif (26KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022246/ng5272Isup2.hkl

e-68-o1845-Isup2.hkl (157KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812022246/ng5272Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯Br1 0.95 2.59 3.538 (3) 175
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supplementary crystallographic information

Comment

Imidazolium salts are precursors for the synthesis of N-heterocyclic carbenes (NHC) and can be prepared according to Arduengo et al. (1995, 1999) and Hintermann (2007). Deprotonation by strong bases gives the free stable NHC, which is widely used as ligands.

The title compound crystallizes with discrete cations, anions and solvent dichloromethane molecules. Both cations and anions are located on a crystallographic mirror plane. Both dichloromethane molecules show a disorder across a mirror plane over two equally occupied positions. The Br anions are connnected to the cations via C—H···Br hydrogen bonds. Structures with the same cation, but with different anions and solvent molecules, have been determined by Stasch et al. (2004), Blue et al. (2006) and Berger et al. (2012). For compounds with 1,3-bis-(2,6-diisopropylphenyl)imidazolium unit, see: Ikhile et al. (2010) and Giffin et al. (2010).

Experimental

1,3-Bis(2,6-di-isopropylphenyl)1H-imidazol-3-ium bromide chloroform disolvate was prepared by reacting 167 mg of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene with 115 mg of Si2Br6 in deuterated dichloromethane. After two weeks at 253 K colorless needles of the title compound crystallized in the NMR-Tube.

Refinement

H atoms were refined using a riding model, with C—H ranging from 0.95 Å to 1.00 Å and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).

Figures

Fig. 1.

Fig. 1.

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A perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding and dichloromethane molecules are omitted for clarity. Atoms labelled with suffix A were generated by the symmetry operator x, -y + 1/2, z.

Crystal data

C27H37N2+·Br−·2CH2Cl2 F(000) = 664
Mr = 639.35 Dx = 1.299 Mg m−3
Monoclinic, P21/m Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb Cell parameters from 19135 reflections
a = 9.1874 (8) Å θ = 3.4–26.0°
b = 16.5165 (12) Å µ = 1.60 mm−1
c = 11.030 (1) Å T = 173 K
β = 102.332 (7)° Plate, colourless
V = 1635.1 (2) Å3 0.52 × 0.28 × 0.24 mm
Z = 2
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Data collection

Stoe IPDS II two-circle diffractometer 3200 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source 2867 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator Rint = 0.084
ω scans θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) h = −11→11
Tmin = 0.489, Tmax = 0.700 k = −19→20
20988 measured reflections l = −13→13
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Refinement

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)] = 0.038 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.041P)2 + 0.9357P] where P = (Fo2 + 2Fc2)/3
3200 reflections (Δ/σ)max < 0.001
197 parameters Δρmax = 0.43 e Å−3
0 restraints Δρmin = −0.36 e Å−3
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Special details

Experimental. ;
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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
N1 0.29660 (18) 0.18481 (10) 0.41051 (15) 0.0255 (4)
C1 0.2134 (3) 0.2500 0.4158 (3) 0.0241 (6)
H1 0.1119 0.2500 0.4222 0.029*
C2 0.4378 (2) 0.20927 (14) 0.4033 (2) 0.0313 (5)
H2 0.5197 0.1751 0.3992 0.038*
C3 0.1307 (3) 0.11525 (15) 0.1796 (2) 0.0440 (6)
H3 0.1846 0.1682 0.1925 0.053*
C4 −0.0359 (4) 0.1327 (2) 0.1415 (3) 0.0594 (8)
H4A −0.0567 0.1626 0.0629 0.089*
H4B −0.0669 0.1652 0.2059 0.089*
H4C −0.0911 0.0815 0.1311 0.089*
C5 0.1838 (3) 0.0696 (2) 0.0773 (3) 0.0545 (7)
H5A 0.1607 0.1012 0.0004 0.082*
H5B 0.1333 0.0171 0.0640 0.082*
H5C 0.2917 0.0611 0.1017 0.082*
C6 0.3631 (3) 0.09778 (16) 0.6435 (2) 0.0394 (5)
H6 0.4138 0.1470 0.6197 0.047*
C7 0.2619 (4) 0.1250 (3) 0.7253 (4) 0.0934 (15)
H7A 0.1868 0.1621 0.6791 0.140*
H7B 0.3203 0.1529 0.7980 0.140*
H7C 0.2123 0.0779 0.7523 0.140*
C8 0.4824 (5) 0.0423 (3) 0.7119 (4) 0.1023 (17)
H8A 0.5472 0.0256 0.6565 0.153*
H8B 0.4361 −0.0057 0.7401 0.153*
H8C 0.5415 0.0707 0.7838 0.153*
C11 0.2443 (2) 0.10184 (13) 0.4124 (2) 0.0317 (5)
C12 0.1641 (3) 0.06934 (14) 0.3013 (2) 0.0382 (5)
C13 0.1118 (4) −0.00958 (16) 0.3072 (3) 0.0531 (7)
H13 0.0559 −0.0343 0.2342 0.064*
C14 0.1396 (4) −0.05222 (16) 0.4166 (3) 0.0578 (8)
H14 0.1019 −0.1057 0.4183 0.069*
C15 0.2209 (3) −0.01857 (16) 0.5234 (3) 0.0500 (7)
H15 0.2401 −0.0494 0.5978 0.060*
C16 0.2761 (3) 0.06008 (14) 0.5248 (2) 0.0366 (5)
Br1 −0.17082 (3) 0.2500 0.41902 (3) 0.03239 (11)
C9 0.6207 (8) 0.2781 (5) 0.1008 (6) 0.083 (4) 0.50
H9A 0.6687 0.2735 0.1899 0.100* 0.309 (13)
H9B 0.6987 0.2657 0.0540 0.100* 0.309 (13)
H9C 0.6825 0.2561 0.0452 0.100* 0.191 (13)
H9D 0.6666 0.2661 0.1886 0.100* 0.191 (13)
Cl1 0.5757 (3) 0.3808 (3) 0.0739 (3) 0.1306 (12) 0.50
Cl2 0.4398 (9) 0.2500 0.0600 (7) 0.091 (3) 0.38 (3)
Cl2' 0.4863 (16) 0.1966 (13) 0.0681 (6) 0.129 (7) 0.309 (13)
C10 0.7893 (8) 0.2231 (4) 0.7366 (6) 0.0643 (18) 0.50
H10A 0.7776 0.2363 0.6475 0.077* 0.50
H10B 0.7760 0.1639 0.7438 0.077* 0.50
Cl3 0.96814 (15) 0.2500 0.81560 (13) 0.0802 (4)
Cl4 0.6535 (2) 0.27308 (11) 0.79502 (16) 0.0803 (7) 0.50
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0245 (9) 0.0254 (8) 0.0255 (8) 0.0012 (7) 0.0030 (7) −0.0009 (7)
C1 0.0239 (14) 0.0225 (14) 0.0246 (14) 0.000 0.0022 (11) 0.000
C2 0.0247 (10) 0.0374 (11) 0.0322 (11) 0.0053 (9) 0.0074 (8) −0.0019 (9)
C3 0.0606 (16) 0.0333 (12) 0.0331 (12) −0.0058 (12) −0.0012 (11) −0.0042 (10)
C4 0.074 (2) 0.0622 (19) 0.0383 (14) 0.0213 (16) 0.0033 (13) −0.0042 (13)
C5 0.0549 (17) 0.0630 (18) 0.0446 (15) 0.0006 (15) 0.0085 (13) −0.0039 (14)
C6 0.0428 (13) 0.0418 (13) 0.0325 (12) 0.0040 (11) 0.0055 (10) 0.0051 (10)
C7 0.057 (2) 0.142 (4) 0.081 (3) 0.000 (2) 0.0153 (19) −0.065 (3)
C8 0.100 (3) 0.100 (3) 0.080 (3) 0.056 (3) −0.042 (2) −0.025 (2)
C11 0.0341 (12) 0.0226 (10) 0.0381 (12) 0.0013 (9) 0.0073 (9) −0.0009 (9)
C12 0.0456 (14) 0.0276 (11) 0.0384 (12) −0.0020 (10) 0.0025 (10) −0.0018 (10)
C13 0.071 (2) 0.0321 (13) 0.0501 (16) −0.0120 (13) 0.0003 (14) −0.0050 (12)
C14 0.081 (2) 0.0268 (13) 0.0620 (18) −0.0124 (13) 0.0074 (16) 0.0036 (12)
C15 0.0673 (19) 0.0345 (13) 0.0484 (15) −0.0004 (13) 0.0128 (14) 0.0118 (11)
C16 0.0396 (13) 0.0321 (12) 0.0381 (12) 0.0050 (10) 0.0082 (10) 0.0048 (10)
Br1 0.02843 (17) 0.03733 (18) 0.03321 (18) 0.000 0.01058 (12) 0.000
C9 0.056 (3) 0.148 (12) 0.041 (3) −0.028 (4) −0.003 (2) −0.009 (4)
Cl1 0.0784 (17) 0.170 (3) 0.129 (2) 0.0489 (19) −0.0110 (16) −0.020 (2)
Cl2 0.068 (3) 0.144 (9) 0.063 (3) 0.000 0.019 (2) 0.000
Cl2' 0.094 (7) 0.234 (17) 0.063 (2) −0.100 (10) 0.024 (3) −0.035 (5)
C10 0.084 (4) 0.064 (4) 0.056 (3) −0.011 (3) 0.039 (3) −0.015 (3)
Cl3 0.0666 (8) 0.1076 (11) 0.0723 (8) 0.000 0.0278 (6) 0.000
Cl4 0.0721 (10) 0.099 (2) 0.0690 (9) 0.0362 (10) 0.0134 (8) −0.0046 (9)
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Geometric parameters (Å, º)

N1—C1 1.329 (2) C11—C12 1.395 (3)
N1—C2 1.377 (3) C12—C13 1.396 (4)
N1—C11 1.454 (3) C13—C14 1.373 (4)
C1—N1i 1.329 (2) C13—H13 0.9500
C1—H1 0.9500 C14—C15 1.371 (4)
C2—C2i 1.346 (5) C14—H14 0.9500
C2—H2 0.9500 C15—C16 1.393 (4)
C3—C12 1.515 (3) C15—H15 0.9500
C3—C5 1.521 (4) C9—Cl2 1.691 (10)
C3—C4 1.525 (4) C9—Cl1 1.757 (10)
C3—H3 1.0000 C9—Cl2' 1.810 (11)
C4—H4A 0.9800 C9—H9A 0.9900
C4—H4B 0.9800 C9—H9B 0.9900
C4—H4C 0.9800 C9—H9C 0.9900
C5—H5A 0.9800 C9—H9D 0.9900
C5—H5B 0.9800 Cl1—Cl2'i 1.51 (3)
C5—H5C 0.9800 Cl2—C9i 1.691 (10)
C6—C7 1.496 (4) Cl2'—C9i 1.280 (11)
C6—C8 1.503 (4) Cl2'—Cl1i 1.51 (3)
C6—C16 1.514 (3) Cl2'—Cl2'i 1.76 (4)
C6—H6 1.0000 C10—Cl4 1.731 (6)
C7—H7A 0.9800 C10—Cl3 1.745 (7)
C7—H7B 0.9800 C10—H10A 0.9900
C7—H7C 0.9800 C10—H10B 0.9900
C8—H8A 0.9800 Cl3—C10i 1.745 (7)
C8—H8B 0.9800 Cl4—Cl4i 0.763 (4)
C8—H8C 0.9800 Cl4—C10i 1.523 (6)
C11—C16 1.394 (3)
C1—N1—C2 108.82 (18) H8A—C8—H8C 109.5
C1—N1—C11 124.62 (18) H8B—C8—H8C 109.5
C2—N1—C11 126.56 (18) C16—C11—C12 124.2 (2)
N1i—C1—N1 108.2 (3) C16—C11—N1 118.2 (2)
N1i—C1—H1 125.9 C12—C11—N1 117.7 (2)
N1—C1—H1 125.9 C11—C12—C13 116.2 (2)
C2i—C2—N1 107.06 (12) C11—C12—C3 123.7 (2)
C2i—C2—H2 126.5 C13—C12—C3 120.1 (2)
N1—C2—H2 126.5 C14—C13—C12 121.2 (3)
C12—C3—C5 111.9 (2) C14—C13—H13 119.4
C12—C3—C4 109.9 (2) C12—C13—H13 119.4
C5—C3—C4 110.6 (2) C15—C14—C13 120.8 (2)
C12—C3—H3 108.1 C15—C14—H14 119.6
C5—C3—H3 108.1 C13—C14—H14 119.6
C4—C3—H3 108.1 C14—C15—C16 121.2 (2)
C3—C4—H4A 109.5 C14—C15—H15 119.4
C3—C4—H4B 109.5 C16—C15—H15 119.4
H4A—C4—H4B 109.5 C15—C16—C11 116.4 (2)
C3—C4—H4C 109.5 C15—C16—C6 121.1 (2)
H4A—C4—H4C 109.5 C11—C16—C6 122.5 (2)
H4B—C4—H4C 109.5 Cl2—C9—Cl1 92.2 (4)
C3—C5—H5A 109.5 Cl2—C9—H9A 116.6
C3—C5—H5B 109.5 Cl1—C9—H9A 106.3
H5A—C5—H5B 109.5 Cl2'—C9—H9A 106.3
C3—C5—H5C 109.5 Cl2—C9—H9B 125.7
H5A—C5—H5C 109.5 Cl1—C9—H9B 106.3
H5B—C5—H5C 109.5 Cl2'—C9—H9B 106.3
C7—C6—C8 111.2 (3) H9A—C9—H9B 106.4
C7—C6—C16 111.3 (2) Cl2—C9—H9C 113.3
C8—C6—C16 112.1 (2) Cl1—C9—H9C 113.3
C7—C6—H6 107.3 Cl2—C9—H9D 113.3
C8—C6—H6 107.3 Cl1—C9—H9D 113.3
C16—C6—H6 107.3 Cl2'—C9—H9D 100.2
C6—C7—H7A 109.5 H9C—C9—H9D 110.6
C6—C7—H7B 109.5 Cl2'i—Cl1—C9 45.3 (3)
H7A—C7—H7B 109.5 Cl1i—Cl2'—C9 106.2 (9)
C6—C7—H7C 109.5 Cl4—C10—Cl3 111.7 (3)
H7A—C7—H7C 109.5 Cl4—C10—H10A 109.3
H7B—C7—H7C 109.5 Cl3—C10—H10A 109.3
C6—C8—H8A 109.5 Cl4—C10—H10B 109.3
C6—C8—H8B 109.5 Cl3—C10—H10B 109.3
H8A—C8—H8B 109.5 H10A—C10—H10B 107.9
C6—C8—H8C 109.5
C2—N1—C1—N1i 0.8 (3) C12—C11—C16—C15 −0.9 (4)
C11—N1—C1—N1i −179.28 (14) N1—C11—C16—C15 178.5 (2)
C1—N1—C2—C2i −0.50 (18) C12—C11—C16—C6 −179.8 (2)
C11—N1—C2—C2i 179.60 (16) N1—C11—C16—C6 −0.4 (3)
C1—N1—C11—C16 −98.5 (3) C7—C6—C16—C15 −77.5 (4)
C2—N1—C11—C16 81.4 (3) C8—C6—C16—C15 47.7 (4)
C1—N1—C11—C12 81.0 (3) C7—C6—C16—C11 101.3 (3)
C2—N1—C11—C12 −99.1 (3) C8—C6—C16—C11 −133.5 (3)
C16—C11—C12—C13 1.2 (4) Cl2—C9—Cl1—Cl2'i 2.7 (5)
N1—C11—C12—C13 −178.1 (2) Cl2'—C9—Cl1—Cl2'i 7.6 (4)
C16—C11—C12—C3 −179.8 (2) Cl1—C9—Cl2—C9i 174.0 (2)
N1—C11—C12—C3 0.8 (4) Cl2'—C9—Cl2—C9i 1.6 (6)
C5—C3—C12—C11 124.9 (3) Cl2—C9—Cl2'—C9i −177.7 (8)
C4—C3—C12—C11 −111.8 (3) Cl1—C9—Cl2'—C9i 173.1 (2)
C5—C3—C12—C13 −56.2 (4) Cl2—C9—Cl2'—Cl1i 175.3 (9)
C4—C3—C12—C13 67.1 (3) Cl1—C9—Cl2'—Cl1i 166.1 (5)
C11—C12—C13—C14 −0.5 (4) Cl2—C9—Cl2'—Cl2'i 2.3 (8)
C3—C12—C13—C14 −179.5 (3) Cl1—C9—Cl2'—Cl2'i −6.9 (2)
C12—C13—C14—C15 −0.6 (5) Cl4—C10—Cl3—C10i −50.6 (3)
C13—C14—C15—C16 0.9 (5) Cl3—C10—Cl4—Cl4i −121.8 (4)
C14—C15—C16—C11 −0.2 (4) Cl3—C10—Cl4—C10i 58.2 (4)
C14—C15—C16—C6 178.7 (3)
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Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C1—H1···Br1 0.95 2.59 3.538 (3) 175
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5272).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022246/ng5272sup1.cif

e-68-o1845-sup1.cif (26KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022246/ng5272Isup2.hkl

e-68-o1845-Isup2.hkl (157KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812022246/ng5272Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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