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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1639.
Published online 2009 November 21. doi:  10.1107/S1600536809046376
PMCID: PMC2972158

1-Butyl-3-(1-naphthyl­meth­yl)benzimidazolium hemi{di-μ-iodido-bis­[diiodidomercurate(II)]} dimethyl sulfoxide monosolvate

Abstract

In the title compound, (C22H23N2)[Hg2I6]0.5·(CH3)2SO, the 1-butyl-3-(1-naphthyl­meth­yl)benzimidazolium anion lies across a centre of inversion. The dihedral angle between the benzimidazolium and naphthalene ring systems is 81.9 (3)°. In the crystal structure, π–π stacking inter­actions are observed between the imidazolium ring and the unsubstituted benzene ring of the naphthalene ring system, with a centroid–centroid separation of 3.510 (5) Å. In the centrosymmetric anion, the Hg(II) atoms are in a distorted tetrahedral coordination. The dimethyl sulfoxide solvent mol­ecule is disordered over two sites with occupancies of 0.615 (9) and 0.385 (9).

Related literature

For background to the chemistry of imidazolium compounds, see: Arduengo et al. (1991 [triangle]); Garrison & Youngs (2005 [triangle]). For a related structure, see: Liu et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1639-scheme1.jpg

Experimental

Crystal data

  • (C22H23N2)[Hg2I6]0.5·C2H6OS
  • M r = 974.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1639-efi1.jpg
  • a = 12.0565 (13) Å
  • b = 13.7312 (16) Å
  • c = 18.378 (2) Å
  • β = 102.089 (2)°
  • V = 2975.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 8.38 mm−1
  • T = 296 K
  • 0.28 × 0.26 × 0.22 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.110, T max = 0.158
  • 14876 measured reflections
  • 5253 independent reflections
  • 3641 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.111
  • S = 1.03
  • 5253 reflections
  • 327 parameters
  • 60 restraints
  • H-atom parameters constrained
  • Δρmax = 1.16 e Å−3
  • Δρmin = −1.71 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046376/ci2946sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046376/ci2946Isup2.hkl

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

Acknowledgments

This project was supported by the National Science Foundation of China (grant No. 20872111) and the Natural Science Foundation of Tianjin (grant No. 07JCYBJC00300).

supplementary crystallographic information

Comment

Since the discovery of free stable N-heterocyclic carbene (NHC) (Arduengo et al., 1991), the carbene chemistry based on imidazol-2-ylidene (imy) or benzimidazol-2-ylidene (bimy) have been receiving considerable attention, owing to their inherent stability, their interesting characteristics of structure and bonding, and their potential for synthesis and as catalysts in organic reactions (Garrison & Youngs, 2005). We report here the synthesis and crystal structure of the title compound (Fig. 1).

The dihedral angle between benzimidazolium and naphthalene ring systems is 81.9 (3)°. The butyl group and 1-naphthylmethyl group lie on the same side of benzimidazole ring system. The N—C and C—N—C angles agree with those observed in 1-(9-anthracenylmethyl)-3-ethylimidazolium iodide (Liu et al., 2003).

The [Hg2I6]2- anionic unit lies across a centre of inversion, in which atoms Hg1, I2, Hg1A and I2A are coplanar, with I2—Hg1—I2A and Hg1—I2—Hg1A angles of 94.29 (2)° and 85.71 (2)°, respectively. All Hg—I bond distances fall in the regular range of 2.6792 (9)–2.8943 (4) Å.

Experimental

A solution of 1-iodobutane (1.583 g, 8.6 mmol) and 1-(1-naphthylmethyl)benzimidazole (1.860 g, 7.2 mmol) in THF (100 ml) was stirred for five days under refluxing, and a pale yellow precipitate was formed. The product was filtred and washed with THF. The powder of benzimidazolium iodide are obtained by recrystallization from methanol/diethyl ether [3.5 g (91%), m.p 188–190°C]. A mixture of benzimidazolium iodide (0.199 g, 0.45 mmol) and mercury(II) iodide (0.245 g, 0.54 mmol) in THF (20 ml) and dichloromethane (20 ml) was refluxed for 24 h. A brown solution was formed and the solvent was removed with a rotary evaporator. Water (30 ml) was added to the residue and the solution was extracted with CH2Cl2 (30 ml). The extracting solution was dried with anhydrate MgSO4, then the solution was concentrated to 10 ml and diethyl ether (5 ml) was added. A pale yellow powder was obtained, and isolation by filtration yielded the title compound [yield 0.401 g (83%), m.p 235–237°C). 1H NMR (300 MHZ, DMSO-d6): 0.97 (t, J = 5.4, 3H, CH3), 1.46 (m, 2H, CH2), 2.03 (m, 2H, CH2), 4.55 (t, J = 7.2, 2H, CH2), 6.31 (s, 2H, CH2), 7.43 (t, J = 6.0, 1H, PhH), 7.55 (d, J = 6.0, 2H, PhH), 7.63 (d, J = 6.3, 4H, PhH), 7.65 (t, J = 8.8, 1H, PhH), 7.91 (d, J = 8.4, 2H, PhH), 8.13 (d, J = 8.4, 1H, PhH), 11.23 (s, 1H, bimiH) (bimi: benzimidazole). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an CH2Cl2 solution at room temperature.

Refinement

The dimethyl sulfoxide solvent molecule is disordered over two sites with occupancies of 0.615 (9) and 0.385 (9). Uij and distance restraints were applied. All H atoms were initially located in a difference Fourier map. They were then placed in geometrically idealized positions and constrained to ride on their parent atoms, with Csp3–H = 0.97 Å, Csp2–H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The highest residual density peak is located 0.95 Å from atom I1 and the deepest hole is located 0.79 Å from atom I2.

Figures

Fig. 1.
The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. Only the major component of the disordered DMSO molecule is shown.

Crystal data

(C22H23N2)[Hg2I6]0.5·C2H6OSF(000) = 1800
Mr = 974.85Dx = 2.177 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3658 reflections
a = 12.0565 (13) Åθ = 2.3–23.9°
b = 13.7312 (16) ŵ = 8.38 mm1
c = 18.378 (2) ÅT = 296 K
β = 102.089 (2)°Block, yellow
V = 2975.0 (6) Å30.28 × 0.26 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer5253 independent reflections
Radiation source: fine-focus sealed tube3641 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.110, Tmax = 0.158k = −16→11
14876 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0474P)2 + 6.0193P] where P = (Fo2 + 2Fc2)/3
5253 reflections(Δ/σ)max = 0.001
327 parametersΔρmax = 1.16 e Å3
60 restraintsΔρmin = −1.71 e Å3

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.

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

xyzUiso*/UeqOcc. (<1)
Hg10.61164 (3)0.57544 (3)0.95810 (2)0.07147 (16)
I10.83044 (5)0.51958 (4)0.98219 (4)0.06220 (19)
I20.47338 (6)0.40737 (6)0.90484 (4)0.0883 (3)
I30.53530 (6)0.73713 (6)0.88235 (5)0.0985 (3)
N1−0.0121 (6)0.4144 (4)0.2680 (3)0.0446 (15)
N20.0684 (5)0.3180 (4)0.3578 (3)0.0433 (15)
C1−0.1740 (8)0.6136 (6)0.2289 (5)0.059 (2)
H1−0.22230.57830.19220.071*
C2−0.2176 (9)0.6929 (7)0.2618 (6)0.071 (3)
H2−0.29380.70920.24680.085*
C3−0.1503 (9)0.7452 (7)0.3148 (5)0.065 (3)
H3−0.18040.79690.33700.078*
C4−0.0332 (8)0.7225 (6)0.3373 (4)0.051 (2)
C50.0393 (9)0.7759 (6)0.3924 (5)0.063 (2)
H50.00990.82690.41580.076*
C60.1503 (10)0.7553 (7)0.4125 (5)0.071 (3)
H60.19660.79160.44950.085*
C70.1962 (9)0.6798 (7)0.3781 (5)0.071 (3)
H70.27320.66580.39220.085*
C80.1289 (7)0.6259 (6)0.3235 (5)0.057 (2)
H80.16140.57690.29990.068*
C90.0119 (7)0.6431 (5)0.3025 (4)0.0476 (19)
C10−0.0635 (7)0.5867 (5)0.2488 (4)0.0460 (19)
C11−0.0249 (7)0.4955 (6)0.2146 (4)0.052 (2)
H11A−0.08010.47820.17000.063*
H11B0.04700.50780.20050.063*
C120.0855 (7)0.3871 (5)0.3116 (4)0.0431 (18)
H120.15600.41310.30960.052*
C13−0.0978 (6)0.3588 (5)0.2866 (4)0.0412 (17)
C14−0.2127 (8)0.3544 (6)0.2578 (5)0.058 (2)
H14−0.24780.39430.21890.069*
C15−0.2726 (8)0.2872 (8)0.2901 (6)0.069 (3)
H15−0.35060.28230.27280.083*
C16−0.2195 (9)0.2262 (7)0.3481 (6)0.070 (3)
H16−0.26320.18130.36770.084*
C17−0.1077 (8)0.2305 (6)0.3763 (5)0.057 (2)
H17−0.07290.19020.41510.068*
C18−0.0465 (7)0.2981 (5)0.3446 (4)0.0445 (18)
C190.1555 (8)0.2795 (6)0.4189 (4)0.058 (2)
H19A0.22990.28930.40780.070*
H19B0.14420.21010.42390.070*
C200.1505 (8)0.3299 (6)0.4918 (5)0.059 (2)
H20A0.07520.32070.50160.071*
H20B0.20390.29810.53150.071*
C210.1762 (9)0.4371 (7)0.4943 (5)0.072 (3)
H21A0.25270.44600.48670.086*
H21B0.12500.46840.45320.086*
C220.1665 (9)0.4881 (8)0.5648 (5)0.084 (3)
H22A0.08980.48370.57150.126*
H22B0.18700.55530.56190.126*
H22C0.21650.45790.60620.126*
S10.5566 (4)0.8983 (4)0.1687 (3)0.0831 (19)0.615 (9)
O10.6734 (8)0.9226 (16)0.1578 (11)0.132 (10)0.615 (9)
C230.5144 (19)0.9966 (15)0.2185 (12)0.127 (11)0.615 (9)
H23A0.55670.99530.26890.191*0.615 (9)
H23B0.43490.99120.21810.191*0.615 (9)
H23C0.52851.05680.19540.191*0.615 (9)
C240.4652 (16)0.921 (2)0.0812 (8)0.160 (13)0.615 (9)
H24A0.47950.87360.04570.241*0.615 (9)
H24B0.47900.98500.06450.241*0.615 (9)
H24C0.38770.91570.08610.241*0.615 (9)
S1'0.5614 (7)0.9773 (6)0.1314 (4)0.089 (3)0.385 (9)
O1'0.6753 (11)0.943 (2)0.1700 (14)0.100 (11)0.385 (9)
C23'0.481 (2)0.995 (2)0.2005 (13)0.077 (9)0.385 (9)
H23D0.51451.04550.23390.116*0.385 (9)
H23E0.47890.93550.22780.116*0.385 (9)
H23F0.40461.01330.17720.116*0.385 (9)
C24'0.485 (2)0.8777 (19)0.0855 (15)0.112 (12)0.385 (9)
H24D0.51970.85690.04540.168*0.385 (9)
H24E0.40830.89680.06590.168*0.385 (9)
H24F0.48660.82500.12000.168*0.385 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.0457 (2)0.0806 (3)0.0874 (3)0.00266 (18)0.01229 (19)0.0094 (2)
I10.0479 (3)0.0505 (3)0.0878 (4)0.0062 (3)0.0134 (3)−0.0007 (3)
I20.0773 (5)0.1162 (6)0.0770 (5)−0.0384 (4)0.0289 (4)−0.0373 (4)
I30.0758 (5)0.1001 (6)0.1121 (6)0.0222 (4)0.0029 (4)0.0270 (5)
N10.060 (4)0.042 (4)0.034 (3)0.004 (3)0.015 (3)−0.001 (3)
N20.051 (4)0.041 (3)0.041 (4)0.007 (3)0.014 (3)0.001 (3)
C10.075 (6)0.050 (5)0.053 (5)0.005 (4)0.013 (5)0.016 (4)
C20.085 (7)0.057 (6)0.076 (7)0.021 (5)0.027 (6)0.018 (5)
C30.099 (8)0.047 (5)0.060 (6)0.015 (5)0.039 (6)0.002 (5)
C40.075 (6)0.039 (4)0.046 (5)0.001 (4)0.029 (4)0.012 (4)
C50.091 (8)0.048 (5)0.059 (6)−0.007 (5)0.035 (5)0.002 (4)
C60.108 (9)0.053 (6)0.057 (6)−0.018 (6)0.025 (6)−0.002 (5)
C70.073 (6)0.057 (6)0.080 (7)−0.015 (5)0.012 (5)0.009 (5)
C80.068 (6)0.043 (5)0.068 (6)−0.002 (4)0.036 (5)0.010 (4)
C90.065 (5)0.038 (4)0.046 (5)0.002 (4)0.026 (4)0.016 (4)
C100.070 (6)0.043 (4)0.028 (4)0.008 (4)0.014 (4)0.009 (3)
C110.068 (5)0.052 (5)0.038 (4)0.005 (4)0.012 (4)0.004 (4)
C120.047 (5)0.044 (4)0.038 (4)0.000 (3)0.009 (4)−0.003 (4)
C130.046 (4)0.042 (4)0.039 (4)0.003 (3)0.016 (4)−0.008 (4)
C140.069 (6)0.055 (5)0.050 (5)0.009 (5)0.014 (4)−0.009 (4)
C150.047 (5)0.086 (7)0.075 (7)−0.012 (5)0.015 (5)−0.027 (6)
C160.076 (7)0.069 (6)0.071 (6)−0.017 (5)0.029 (6)−0.004 (5)
C170.071 (6)0.055 (5)0.049 (5)−0.008 (4)0.024 (5)0.002 (4)
C180.057 (5)0.042 (4)0.038 (4)0.003 (4)0.017 (4)−0.006 (4)
C190.064 (5)0.053 (5)0.056 (5)0.006 (4)0.008 (4)0.007 (4)
C200.062 (5)0.063 (6)0.048 (5)−0.004 (4)0.002 (4)0.010 (4)
C210.079 (7)0.080 (7)0.058 (6)−0.003 (5)0.018 (5)0.004 (5)
C220.099 (8)0.098 (8)0.058 (6)−0.015 (7)0.022 (6)−0.016 (6)
S10.078 (3)0.085 (3)0.094 (3)0.016 (2)0.036 (2)0.019 (2)
O10.119 (11)0.140 (11)0.139 (11)0.006 (5)0.033 (5)−0.008 (5)
C230.128 (12)0.129 (12)0.127 (12)0.003 (5)0.030 (5)−0.004 (5)
C240.159 (13)0.161 (13)0.161 (13)0.004 (5)0.033 (6)−0.001 (5)
S1'0.093 (4)0.086 (5)0.098 (5)0.007 (3)0.043 (3)0.009 (3)
O1'0.090 (12)0.107 (12)0.108 (12)0.004 (5)0.028 (5)−0.008 (5)
C23'0.077 (10)0.079 (10)0.077 (10)0.002 (5)0.019 (5)−0.004 (5)
C24'0.110 (13)0.111 (13)0.114 (13)0.002 (5)0.024 (6)−0.003 (5)

Geometric parameters (Å, °)

Hg1—I32.6792 (9)C15—C161.402 (13)
Hg1—I12.6933 (7)C15—H150.93
Hg1—I22.8943 (5)C16—C171.341 (12)
Hg1—I22.8943 (4)C16—H160.93
I2—Hg12.8943 (4)C17—C181.387 (11)
N1—C121.331 (9)C17—H170.93
N1—C131.384 (9)C19—C201.519 (12)
N1—C111.472 (9)C19—H19A0.97
N2—C121.318 (9)C19—H19B0.97
N2—C181.383 (9)C20—C211.503 (12)
N2—C191.466 (10)C20—H20A0.97
C1—C101.357 (11)C20—H20B0.97
C1—C21.400 (13)C21—C221.498 (13)
C1—H10.93C21—H21A0.97
C2—C31.339 (13)C21—H21B0.97
C2—H20.93C22—H22A0.96
C3—C41.420 (13)C22—H22B0.96
C3—H30.93C22—H22C0.96
C4—C51.400 (12)S1—O11.5010 (9)
C4—C91.428 (11)S1—C231.7650 (9)
C5—C61.342 (14)S1—C241.7750 (9)
C5—H50.93C23—H23A0.96
C6—C71.387 (14)C23—H23B0.96
C6—H60.93C23—H23C0.96
C7—C81.368 (12)C24—H24A0.96
C7—H70.93C24—H24B0.96
C8—C91.403 (11)C24—H24C0.96
C8—H80.93S1'—O1'1.484 (10)
C9—C101.423 (11)S1'—C24'1.761 (10)
C10—C111.518 (11)S1'—C23'1.771 (9)
C11—H11A0.97C23'—H23D0.96
C11—H11B0.97C23'—H23E0.96
C12—H120.9300C23'—H23F0.96
C13—C141.376 (11)C24'—H24D0.96
C13—C181.392 (10)C24'—H24E0.96
C14—C151.380 (13)C24'—H24F0.96
C14—H140.93
I3—Hg1—I1122.65 (3)C17—C16—H16119.0
I3—Hg1—I2111.97 (3)C15—C16—H16119.0
I1—Hg1—I2107.66 (3)C16—C17—C18116.6 (9)
I3—Hg1—I2i103.69 (3)C16—C17—H17121.7
I1—Hg1—I2i112.94 (3)C18—C17—H17121.7
I2—Hg1—I2i94.29 (2)N2—C18—C17131.3 (8)
Hg1—I2—Hg1i85.71 (2)N2—C18—C13106.5 (6)
C12—N1—C13108.0 (6)C17—C18—C13122.1 (8)
C12—N1—C11124.8 (7)N2—C19—C20110.9 (7)
C13—N1—C11127.1 (7)N2—C19—H19A109.5
C12—N2—C18108.4 (6)C20—C19—H19A109.5
C12—N2—C19124.8 (7)N2—C19—H19B109.5
C18—N2—C19126.4 (7)C20—C19—H19B109.5
C10—C1—C2122.1 (9)H19A—C19—H19B108.0
C10—C1—H1118.9C21—C20—C19115.3 (8)
C2—C1—H1118.9C21—C20—H20A108.4
C3—C2—C1120.4 (9)C19—C20—H20A108.4
C3—C2—H2119.8C21—C20—H20B108.4
C1—C2—H2119.8C19—C20—H20B108.4
C2—C3—C4120.6 (8)H20A—C20—H20B107.5
C2—C3—H3119.7C22—C21—C20115.6 (9)
C4—C3—H3119.7C22—C21—H21A108.4
C5—C4—C3121.9 (8)C20—C21—H21A108.4
C5—C4—C9119.0 (8)C22—C21—H21B108.4
C3—C4—C9119.1 (8)C20—C21—H21B108.4
C6—C5—C4121.6 (9)H21A—C21—H21B107.4
C6—C5—H5119.2C21—C22—H22A109.5
C4—C5—H5119.2C21—C22—H22B109.5
C5—C6—C7120.1 (10)H22A—C22—H22B109.5
C5—C6—H6119.9C21—C22—H22C109.5
C7—C6—H6119.9H22A—C22—H22C109.5
C8—C7—C6120.5 (10)H22B—C22—H22C109.5
C8—C7—H7119.8O1—S1—C23106.2 (8)
C6—C7—H7119.8O1—S1—C24105.2 (7)
C7—C8—C9121.2 (9)C23—S1—C2498.3 (6)
C7—C8—H8119.4S1—C23—H23A109.5
C9—C8—H8119.4S1—C23—H23B109.5
C8—C9—C10124.0 (7)H23A—C23—H23B109.5
C8—C9—C4117.5 (8)S1—C23—H23C109.5
C10—C9—C4118.6 (8)H23A—C23—H23C109.5
C1—C10—C9119.2 (7)H23B—C23—H23C109.5
C1—C10—C11118.8 (8)S1—C24—H24A109.5
C9—C10—C11122.0 (7)S1—C24—H24B109.5
N1—C11—C10110.3 (6)H24A—C24—H24B109.5
N1—C11—H11A109.6S1—C24—H24C109.5
C10—C11—H11A109.6H24A—C24—H24C109.5
N1—C11—H11B109.6H24B—C24—H24C109.5
C10—C11—H11B109.6O1'—S1'—C24'108.6 (8)
H11A—C11—H11B108.1O1'—S1'—C23'107.1 (8)
N2—C12—N1110.6 (7)C24'—S1'—C23'98.1 (7)
N2—C12—H12124.7S1'—C23'—H23D109.5
N1—C12—H12124.7S1'—C23'—H23E109.5
C14—C13—N1132.3 (8)H23D—C23'—H23E109.5
C14—C13—C18121.2 (8)S1'—C23'—H23F109.5
N1—C13—C18106.5 (6)H23D—C23'—H23F109.5
C13—C14—C15116.1 (8)H23E—C23'—H23F109.5
C13—C14—H14122.0S1'—C24'—H24D109.5
C15—C14—H14122.0S1'—C24'—H24E109.5
C14—C15—C16122.0 (8)H24D—C24'—H24E109.5
C14—C15—H15119.0S1'—C24'—H24F109.5
C16—C15—H15119.0H24D—C24'—H24F109.5
C17—C16—C15121.9 (9)H24E—C24'—H24F109.5
I3—Hg1—I2—Hg1i−106.63 (3)C18—N2—C12—N10.0 (8)
I1—Hg1—I2—Hg1i115.73 (3)C19—N2—C12—N1−172.5 (6)
I2i—Hg1—I2—Hg1i0.0C13—N1—C12—N2−0.7 (8)
C10—C1—C2—C30.0 (13)C11—N1—C12—N2174.5 (6)
C1—C2—C3—C41.3 (13)C12—N1—C13—C14−177.3 (8)
C2—C3—C4—C5180.0 (8)C11—N1—C13—C147.7 (12)
C2—C3—C4—C90.2 (12)C12—N1—C13—C181.1 (8)
C3—C4—C5—C6−178.7 (8)C11—N1—C13—C18−174.0 (6)
C9—C4—C5—C61.1 (12)N1—C13—C14—C15178.6 (7)
C4—C5—C6—C70.4 (13)C18—C13—C14—C150.4 (11)
C5—C6—C7—C80.1 (14)C13—C14—C15—C16−0.8 (13)
C6—C7—C8—C9−2.0 (13)C14—C15—C16—C170.9 (14)
C7—C8—C9—C10−176.8 (7)C15—C16—C17—C18−0.6 (13)
C7—C8—C9—C43.4 (11)C12—N2—C18—C17177.9 (8)
C5—C4—C9—C8−2.9 (10)C19—N2—C18—C17−9.7 (13)
C3—C4—C9—C8176.9 (7)C12—N2—C18—C130.7 (8)
C5—C4—C9—C10177.3 (7)C19—N2—C18—C13173.1 (7)
C3—C4—C9—C10−2.9 (10)C16—C17—C18—N2−176.7 (8)
C2—C1—C10—C9−2.8 (12)C16—C17—C18—C130.1 (12)
C2—C1—C10—C11175.5 (7)C14—C13—C18—N2177.5 (7)
C8—C9—C10—C1−175.6 (7)N1—C13—C18—N2−1.1 (7)
C4—C9—C10—C14.2 (10)C14—C13—C18—C17−0.1 (11)
C8—C9—C10—C116.1 (11)N1—C13—C18—C17−178.7 (7)
C4—C9—C10—C11−174.1 (6)C12—N2—C19—C2095.8 (9)
C12—N1—C11—C10−97.1 (9)C18—N2—C19—C20−75.3 (9)
C13—N1—C11—C1077.2 (9)N2—C19—C20—C21−63.9 (10)
C1—C10—C11—N1−102.6 (8)C19—C20—C21—C22177.5 (8)
C9—C10—C11—N175.7 (9)

Symmetry codes: (i) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2946).

References

  • Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363.
  • Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Garrison, J. C. & Youngs, W. J. (2005). Chem. Rev. 105, 3978–4008. [PubMed]
  • Liu, Q. X., Xu, F. B., Li, Q. S., Zeng, X. S., Leng, X. B., Chou, Y. L. & Zhang, Z. Z. (2003). Organometallics, 22, 309–314.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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