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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):o1844. doi: 10.1107/S1600536812022234

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

Matthias Berger a, Norbert Auner a, Michael Bolte a,*
PMCID: PMC3379413  PMID: 22719611

Abstract

In the title compound, C27H37N2 +·Cl−·2CH2Cl2, the cation and the anion are each located on a crystallographic mirror plane. Both of the dichloro­methane solvent mol­ecules show a disorder across a mirror plane over two equally occupied positions. Additionally, one isopropyl group is also disordered. In the crystal, the cations are connected to the chloride ions via C—H⋯Cl 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-o1844-scheme1.jpg

Experimental  

Crystal data  

  • C27H37N2 +·Cl−·2CH2Cl2

  • M r = 594.89

  • Monoclinic, Inline graphic

  • a = 9.1117 (4) Å

  • b = 16.4990 (8) Å

  • c = 10.8875 (6) Å

  • β = 101.068 (4)°

  • V = 1606.32 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 173 K

  • 0.32 × 0.29 × 0.14 mm

Data collection  

  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.864, T max = 0.937

  • 17793 measured reflections

  • 2934 independent reflections

  • 2648 reflections with I > 2σ(I)

  • R int = 0.067

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.075

  • wR(F 2) = 0.184

  • S = 1.04

  • 2934 reflections

  • 185 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 1.36 e Å−3

  • Δρmin = −1.60 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/S1600536812022234/ng5271sup1.cif

e-68-o1844-sup1.cif (26.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022234/ng5271Isup2.hkl

e-68-o1844-Isup2.hkl (144KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812022234/ng5271Isup3.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⋯Cl1 0.95 2.50 3.447 (4) 176
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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. Additionally, one isopropyl group is disordered as well. The Cl anions are connnected to the cations via C—H···Cl 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 the 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 chloride chloroform disolvate was prepared by reacting 0.05 g of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene with 0.05 ml of SiCl4 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). The C—Cl distances of the dichloromethane molecules were restrained to be equal within an effective e.s.d. of 0.02 Å.

The highest maximum (1.34 e/Å3) in the final difference map is at 0.82 Å from Cl41 and the deepest hole (-1.59 e/Å3) is at 0.40 Å from Cl41.

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. The minor occupied methyl groups, 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 + 3/2, z.

Crystal data

C27H37N2+·Cl−·2CH2Cl2 F(000) = 628
Mr = 594.89 Dx = 1.230 Mg m−3
Monoclinic, P21/m Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb Cell parameters from 27732 reflections
a = 9.1117 (4) Å θ = 3.3–28.0°
b = 16.4990 (8) Å µ = 0.47 mm−1
c = 10.8875 (6) Å T = 173 K
β = 101.068 (4)° Plate, colourless
V = 1606.32 (14) Å3 0.32 × 0.29 × 0.14 mm
Z = 2
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Data collection

Stoe IPDS II two-circle diffractometer 2934 independent reflections
Radiation source: fine-focus sealed tube 2648 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.067
ω scans θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) h = −10→10
Tmin = 0.864, Tmax = 0.937 k = −19→19
17793 measured reflections l = −12→12
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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)] = 0.075 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184 H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0696P)2 + 3.4645P] where P = (Fo2 + 2Fc2)/3
2934 reflections (Δ/σ)max < 0.001
185 parameters Δρmax = 1.36 e Å−3
6 restraints Δρmin = −1.60 e Å−3
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Special details

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)
Cl1 0.66661 (12) 0.2500 0.57563 (10) 0.0339 (3)
N1 0.2042 (3) 0.31549 (14) 0.5835 (2) 0.0248 (5)
C1 0.2891 (4) 0.2500 0.5788 (3) 0.0245 (8)
H1 0.3918 0.2500 0.5730 0.029*
C2 0.0606 (3) 0.29075 (18) 0.5907 (3) 0.0289 (6)
H2 −0.0222 0.3250 0.5948 0.035*
C11 0.2556 (3) 0.39874 (17) 0.5807 (3) 0.0298 (6)
C12 0.2225 (4) 0.44066 (19) 0.4672 (3) 0.0356 (7)
C13 0.2757 (4) 0.5201 (2) 0.4671 (3) 0.0484 (9)
H13 0.2547 0.5510 0.3921 0.058*
C14 0.3582 (5) 0.5546 (2) 0.5738 (4) 0.0571 (10)
H14 0.3955 0.6081 0.5711 0.068*
C15 0.3866 (5) 0.5115 (2) 0.6843 (4) 0.0503 (9)
H15 0.4419 0.5365 0.7574 0.060*
C16 0.3359 (4) 0.43202 (18) 0.6913 (3) 0.0358 (7)
C21 0.1357 (4) 0.4026 (2) 0.3483 (3) 0.0386 (7)
H21 0.1064 0.3468 0.3703 0.046*
C22 0.2339 (9) 0.3934 (6) 0.2452 (8) 0.054 (2)* 0.50
H22A 0.3048 0.3487 0.2676 0.081* 0.50
H22B 0.2890 0.4438 0.2393 0.081* 0.50
H22C 0.1691 0.3820 0.1643 0.081* 0.50
C23 −0.0049 (9) 0.4473 (5) 0.2962 (8) 0.0508 (18)* 0.50
H23A 0.0003 0.5021 0.3314 0.076* 0.50
H23B −0.0905 0.4185 0.3180 0.076* 0.50
H23C −0.0169 0.4505 0.2049 0.076* 0.50
C22' 0.2392 (8) 0.3593 (5) 0.2818 (7) 0.0421 (16)* 0.50
H22D 0.1995 0.3606 0.1916 0.063* 0.50
H22E 0.2495 0.3029 0.3105 0.063* 0.50
H22F 0.3373 0.3858 0.2994 0.063* 0.50
C23' 0.0432 (10) 0.4686 (5) 0.2642 (8) 0.055 (2)* 0.50
H23D −0.0477 0.4442 0.2157 0.082* 0.50
H23E 0.1035 0.4912 0.2069 0.082* 0.50
H23F 0.0159 0.5120 0.3171 0.082* 0.50
C61 0.3705 (4) 0.3863 (2) 0.8146 (3) 0.0405 (8)
H61 0.3160 0.3334 0.8034 0.049*
C62 0.5383 (5) 0.3685 (3) 0.8486 (3) 0.0561 (10)
H62A 0.5600 0.3388 0.9281 0.084*
H62B 0.5941 0.4196 0.8571 0.084*
H62C 0.5680 0.3356 0.7826 0.084*
C63 0.3195 (4) 0.4323 (2) 0.9205 (3) 0.0484 (9)
H63A 0.3446 0.4008 0.9981 0.073*
H63B 0.2111 0.4406 0.8995 0.073*
H63C 0.3701 0.4849 0.9321 0.073*
C3 0.8708 (8) 0.2675 (6) 0.8843 (7) 0.065 (4) 0.50
H3A 0.8224 0.2614 0.7953 0.078* 0.50
H3B 0.7940 0.2572 0.9355 0.078* 0.50
Cl31 0.9337 (5) 0.3663 (3) 0.9093 (4) 0.1291 (19) 0.50
Cl32 1.0117 (5) 0.1947 (4) 0.9208 (3) 0.149 (2) 0.50
C4 0.7100 (8) 0.2771 (5) 1.2652 (7) 0.059 (2) 0.50
H4A 0.7124 0.3367 1.2759 0.070* 0.50
H4B 0.7219 0.2526 1.3495 0.070* 0.50
Cl41 0.8547 (2) 0.2500 1.20316 (19) 0.1263 (12)
Cl42 0.53459 (19) 0.2500 1.18007 (18) 0.0806 (6)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.0375 (6) 0.0356 (6) 0.0296 (5) 0.000 0.0092 (4) 0.000
N1 0.0280 (12) 0.0222 (11) 0.0227 (11) 0.0004 (9) 0.0016 (9) 0.0000 (9)
C1 0.027 (2) 0.0238 (19) 0.0214 (18) 0.000 0.0013 (15) 0.000
C2 0.0276 (14) 0.0323 (14) 0.0268 (14) 0.0045 (12) 0.0057 (11) 0.0000 (12)
C11 0.0357 (15) 0.0213 (14) 0.0319 (15) −0.0007 (12) 0.0049 (12) 0.0020 (11)
C12 0.0413 (17) 0.0313 (16) 0.0339 (16) 0.0033 (13) 0.0068 (13) 0.0055 (13)
C13 0.065 (2) 0.0337 (18) 0.046 (2) −0.0017 (17) 0.0090 (17) 0.0153 (15)
C14 0.078 (3) 0.0266 (17) 0.064 (2) −0.0151 (18) 0.007 (2) 0.0070 (17)
C15 0.067 (2) 0.0305 (17) 0.048 (2) −0.0128 (17) −0.0005 (18) −0.0024 (15)
C16 0.0461 (18) 0.0249 (15) 0.0341 (16) −0.0035 (13) 0.0021 (13) −0.0012 (12)
C21 0.0444 (18) 0.0400 (18) 0.0304 (16) 0.0031 (14) 0.0048 (13) 0.0074 (13)
C61 0.057 (2) 0.0294 (16) 0.0303 (16) −0.0070 (15) −0.0027 (14) −0.0027 (13)
C62 0.071 (3) 0.058 (2) 0.0366 (19) 0.023 (2) 0.0040 (17) −0.0019 (17)
C63 0.050 (2) 0.054 (2) 0.0386 (18) −0.0005 (17) 0.0038 (15) −0.0060 (16)
C3 0.046 (4) 0.102 (14) 0.044 (3) 0.020 (5) −0.001 (3) 0.011 (5)
Cl31 0.089 (3) 0.175 (5) 0.109 (3) −0.071 (3) −0.017 (2) 0.025 (3)
Cl32 0.116 (3) 0.282 (7) 0.0525 (16) 0.131 (4) 0.0274 (17) 0.040 (2)
C4 0.073 (5) 0.061 (6) 0.051 (4) −0.013 (4) 0.034 (4) −0.012 (3)
Cl41 0.0594 (11) 0.259 (4) 0.0599 (11) 0.000 0.0088 (9) 0.000
Cl42 0.0583 (10) 0.1116 (15) 0.0758 (11) 0.000 0.0227 (8) 0.000
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Geometric parameters (Å, º)

N1—C1 1.335 (3) C22'—H22D 0.9800
N1—C2 1.388 (4) C22'—H22E 0.9800
N1—C11 1.453 (4) C22'—H22F 0.9800
C1—N1i 1.335 (3) C23'—H23D 0.9800
C1—H1 0.9500 C23'—H23E 0.9800
C2—C2i 1.345 (6) C23'—H23F 0.9800
C2—H2 0.9500 C61—C63 1.525 (5)
C11—C16 1.395 (4) C61—C62 1.531 (5)
C11—C12 1.398 (4) C61—H61 1.0000
C12—C13 1.398 (5) C62—H62A 0.9800
C12—C21 1.517 (4) C62—H62B 0.9800
C13—C14 1.379 (5) C62—H62C 0.9800
C13—H13 0.9500 C63—H63A 0.9800
C14—C15 1.378 (5) C63—H63B 0.9800
C14—H14 0.9500 C63—H63C 0.9800
C15—C16 1.398 (5) C3—Cl31 1.732 (11)
C15—H15 0.9500 C3—Cl32 1.748 (9)
C16—C61 1.519 (4) C3—H3A 0.9900
C21—C22' 1.479 (8) C3—H3B 0.9900
C21—C23 1.493 (8) Cl31—Cl32i 1.225 (7)
C21—C23' 1.562 (9) Cl32—Cl31i 1.225 (7)
C21—C22 1.572 (9) Cl32—C3i 1.414 (9)
C21—H21 1.0000 Cl32—Cl32i 1.825 (13)
C22—H22A 0.9800 C4—Cl41 1.654 (7)
C22—H22B 0.9800 C4—Cl42 1.744 (7)
C22—H22C 0.9800 C4—H4A 0.9900
C23—H23A 0.9800 C4—H4B 0.9900
C23—H23B 0.9800 Cl41—C4i 1.654 (7)
C23—H23C 0.9800 Cl42—C4i 1.744 (7)
C1—N1—C2 108.9 (2) C21—C23—H23C 109.5
C1—N1—C11 124.9 (2) H23A—C23—H23C 109.5
C2—N1—C11 126.2 (2) H23B—C23—H23C 109.5
N1i—C1—N1 108.0 (3) C21—C22'—H22D 109.5
N1i—C1—H1 126.0 C21—C22'—H22E 109.5
N1—C1—H1 126.0 H22D—C22'—H22E 109.5
C2i—C2—N1 107.11 (15) C21—C22'—H22F 109.5
C2i—C2—H2 126.4 H22D—C22'—H22F 109.5
N1—C2—H2 126.4 H22E—C22'—H22F 109.5
C16—C11—C12 123.8 (3) C21—C23'—H23D 109.5
C16—C11—N1 118.1 (3) C21—C23'—H23E 109.5
C12—C11—N1 118.1 (3) H23D—C23'—H23E 109.5
C11—C12—C13 116.7 (3) C21—C23'—H23F 109.5
C11—C12—C21 122.6 (3) H23D—C23'—H23F 109.5
C13—C12—C21 120.8 (3) H23E—C23'—H23F 109.5
C14—C13—C12 121.2 (3) C16—C61—C63 112.3 (3)
C14—C13—H13 119.4 C16—C61—C62 109.7 (3)
C12—C13—H13 119.4 C63—C61—C62 110.4 (3)
C15—C14—C13 120.3 (3) C16—C61—H61 108.1
C15—C14—H14 119.9 C63—C61—H61 108.1
C13—C14—H14 119.9 C62—C61—H61 108.1
C14—C15—C16 121.5 (3) C61—C62—H62A 109.5
C14—C15—H15 119.3 C61—C62—H62B 109.5
C16—C15—H15 119.3 H62A—C62—H62B 109.5
C11—C16—C15 116.5 (3) C61—C62—H62C 109.5
C11—C16—C61 123.6 (3) H62A—C62—H62C 109.5
C15—C16—C61 119.9 (3) H62B—C62—H62C 109.5
C22'—C21—C23 129.3 (5) C61—C63—H63A 109.5
C22'—C21—C12 109.9 (4) C61—C63—H63B 109.5
C23—C21—C12 112.9 (4) H63A—C63—H63B 109.5
C22'—C21—C23' 111.9 (5) C61—C63—H63C 109.5
C12—C21—C23' 110.2 (4) H63A—C63—H63C 109.5
C23—C21—C22 109.9 (5) H63B—C63—H63C 109.5
C12—C21—C22 112.0 (4) Cl31—C3—Cl32 113.9 (5)
C23'—C21—C22 88.0 (5) Cl31—C3—H3A 108.8
C22'—C21—H21 84.1 Cl32—C3—H3A 108.8
C23—C21—H21 107.2 Cl31—C3—H3B 108.8
C12—C21—H21 107.2 Cl32—C3—H3B 108.8
C23'—C21—H21 130.0 H3A—C3—H3B 107.7
C22—C21—H21 107.2 Cl32i—Cl31—C3 53.9 (4)
C21—C22—H22A 109.5 Cl31i—Cl32—C3i 81.7 (5)
C21—C22—H22B 109.5 Cl31i—Cl32—C3 98.9 (5)
H22A—C22—H22B 109.5 Cl31i—Cl32—Cl32i 145.3 (3)
C21—C22—H22C 109.5 Cl41—C4—Cl42 115.8 (4)
H22A—C22—H22C 109.5 Cl41—C4—H4A 108.3
H22B—C22—H22C 109.5 Cl42—C4—H4A 108.3
C21—C23—H23A 109.5 Cl41—C4—H4B 108.3
C21—C23—H23B 109.5 Cl42—C4—H4B 108.3
H23A—C23—H23B 109.5 H4A—C4—H4B 107.4
C2—N1—C1—N1i −0.4 (4) C14—C15—C16—C11 0.1 (6)
C11—N1—C1—N1i 179.95 (19) C14—C15—C16—C61 179.5 (4)
C1—N1—C2—C2i 0.3 (2) C11—C12—C21—C22' −87.2 (5)
C11—N1—C2—C2i 179.9 (2) C13—C12—C21—C22' 91.7 (5)
C1—N1—C11—C16 −79.7 (4) C11—C12—C21—C23 120.6 (5)
C2—N1—C11—C16 100.8 (3) C13—C12—C21—C23 −60.5 (6)
C1—N1—C11—C12 100.0 (4) C11—C12—C21—C23' 149.1 (5)
C2—N1—C11—C12 −79.6 (4) C13—C12—C21—C23' −32.1 (5)
C16—C11—C12—C13 0.7 (5) C11—C12—C21—C22 −114.7 (5)
N1—C11—C12—C13 −178.9 (3) C13—C12—C21—C22 64.2 (5)
C16—C11—C12—C21 179.6 (3) C11—C16—C61—C63 −125.9 (3)
N1—C11—C12—C21 0.0 (4) C15—C16—C61—C63 54.7 (5)
C11—C12—C13—C14 0.7 (5) C11—C16—C61—C62 110.9 (4)
C21—C12—C13—C14 −178.2 (4) C15—C16—C61—C62 −68.4 (4)
C12—C13—C14—C15 −1.7 (7) Cl32—C3—Cl31—Cl32i 4.6 (3)
C13—C14—C15—C16 1.2 (7) Cl31—C3—Cl32—Cl31i 172.1 (6)
C12—C11—C16—C15 −1.1 (5) Cl31—C3—Cl32—C3i 176.6 (3)
N1—C11—C16—C15 178.5 (3) Cl31—C3—Cl32—Cl32i −3.4 (3)
C12—C11—C16—C61 179.5 (3) Cl42—C4—Cl41—C4i −64.5 (5)
N1—C11—C16—C61 −0.9 (5) Cl41—C4—Cl42—C4i 64.0 (5)
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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···Cl1 0.95 2.50 3.447 (4) 176
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5271).

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/S1600536812022234/ng5271sup1.cif

e-68-o1844-sup1.cif (26.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022234/ng5271Isup2.hkl

e-68-o1844-Isup2.hkl (144KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812022234/ng5271Isup3.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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