{3,3′-Bis[(anthracen-9-yl)meth­yl]-1,1′-[(ethane-1,2-diyldi­oxy)bis­(ethane-1,2-di­yl)]bis­(imidazol-2-yl­idene)}mercury(II) bis­(hexa­fluoridophosphate) acetonitrile disolvate

Wang, J.-W.; Guo, Y.; Dong, G.-Y.; Gu, Y.; Bai, D.-S.

doi:10.1107/S1600536812005958

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m302

doi:10.1107/S1600536812005958

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{3,3′-Bis[(anthracen-9-yl)methyl]-1,1′-[(ethane-1,2-diyldioxy)bis(ethane-1,2-diyl)]bis(imidazol-2-ylidene)}mercury(II) bis(hexafluoridophosphate) acetonitrile disolvate

Jun-Wen Wang,^a ^* Yue Guo,^a Gui-Ying Dong,^b Yu Gu ^c and Di-Si Bai ^c

^aCollege of Chemical and Materials Science, Shanxi Normal University, Linfen 041004, People's Republic of China, ^bCollege of Chemical Engineering, Hebei United University, Tangshan 063009, People's Republic of China, and ^cQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: wjwchlwx@126.com

(Received 6 February 2012; accepted 10 February 2012; online 17 February 2012)

In the title compound, [Hg(C₄₂H₃₈N₄O₂)](PF₆)₂·2CH₃CN, the Hg^II cation lies on a twofold axis which is also the internal symmetry element of the complete cationic complex. The Hg^II cation is coordinated by two symmetry-related C(carbene) atoms [Hg—C = 2.058 (9) Å] in a nearly linear geometry, with a C—Hg—C angle of 175.8 (5)°. There are weak intermolecular C—H⋯F interactions in the crystal packing between an F atom of a hexafluoridophosphate anion and a –CH₂– group of the bis-N-heterocyclic carbene ligand.

Related literature

For related bis-N-heterocyclic carbene structures, see: Arduengo et al. (1991 ); Nielsen et al. (2006 ); Guo & Dong (2009 ).

Experimental

Crystal data

[Hg(C₄₂H₃₈N₄O₂)](PF₆)₂·2C₂H₃N
M_r = 1203.4
Orthorhombic, P b c n
a = 19.774 (5) Å
b = 9.774 (3) Å
c = 24.250 (6) Å
V = 4687 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.45 mm⁻¹
T = 298 K
0.24 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan SADABS (Sheldrick, 1996 ) T_min = 0.775, T_max = 0.864
25351 measured reflections
4804 independent reflections
3011 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.169
S = 1.10
4804 reflections
313 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.46 e Å⁻³
Δρ_min = −1.80 e Å⁻³

Table 1
Selected bond lengths (Å)

Hg1—C1	2.058 (9)
P1—F5	1.561 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯F5	0.97	2.48	3.265 (13)	137

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005958/vn2031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005958/vn2031Isup2.hkl

checkCIF report

Comment top

N-heterocyclic carbene (NHC) ligands derived from imidazolium salts have seen an increasing use in organometallic chemistry and homogeneous catalysis (Arduengo et al.,1991). The mercury and silver complexes of bis-NHC ligands bearing a weakly coordinating ether functionality have been reported before (Guo & Dong, 2009; Nielsen et al., 2006). To study further the coordination chemistry of this kind of ligands, we report here the crystal structure of the title complex, (I)

The asymmetric unit of the title compound [C₄₂H₃₈HgN₄O₂]²⁺.2(PF₆)^-.2CH₃CN (I) consists of one half of the [3,3'-Bis(9-anthracenylmethyl)-1,1'-(2,2'-oxydiethylene)bis-(imidazol- 2-ylidene)]mercury(II) cation, one hexafluorophosphate anion and one acetonitrile solvate molecule. The complete complex (Fig. 1) is generated by a crystallographic two-fold axis on which the Hg^II cation is situated. The Hg^II cation of (I) is coordinated by an anthracenyl-carbene ligand adopting a cis-conformation, the geometry of the Hg^II coordination being nearly linear, formed by two symmetry related C(carbene) atoms [Hg—C = 2.058 (9) Å, C— Hg—C = 175.8 (5)°]. The crystal packing exhibits intermolecular C—H···F weak interaction between the organic C atoms and the F atom of hexafluorophosphate anion with H4B···F distance of 2.48 Å.

Related literature top

For related bis-N-heterocyclic carbene structures, see: Arduengo et al. (1991); Nielsen et al. (2006); Guo & Dong (2009).

Experimental top

[3,3'-Bis(9-anthracenylmethyl)-1,1'-(2,2'- oxydiethylene)bis-imidazolium] hexafluorophosphate salt (522 mg, 0.566 mmol) was mixed with anhydrous Hg(OAc)₂ (181 mg, 0.566 mmol) in acetonitrile (100 ml) (under argon) and heated under reflux for 2 d and then cooled to room temperature. The acetonitrile was removed in vacuo to yield a white solid which was washed with methanol to give the crude product. Colourless single crystals of the title compound were obtained by recrystallization from acetonitile and ethyl ether (yield: 75.3%).

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 showing atomic displacement ellipsoids at the 30% probability level [symmetry code A: -x, y, 0.5 - z]. H atoms are omitted for clarity.

{3,3'-Bis[(anthracen-9-yl)methyl]-1,1'-[(ethane-1,2-diyldioxy)bis(ethane- 1,2-diyl)]bis(imidazol-2-ylidene)}mercury(II) bis(hexafluoridophosphate) acetonitrile disolvate top

Crystal data top

[Hg(C₄₂H₃₈N₄O₂)](PF₆)₂·2C₂H₃N	F(000) = 2384
M_r = 1203.4	D_x = 1.705 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 990 reflections
a = 19.774 (5) Å	θ = 2.7–24.2°
b = 9.774 (3) Å	µ = 3.45 mm⁻¹
c = 24.250 (6) Å	T = 298 K
V = 4687 (2) Å³	Block, colourless
Z = 4	0.24 × 0.08 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4804 independent reflections
Radiation source: fine-focus sealed tube	3011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −24→21
T_min = 0.775, T_max = 0.864	k = −8→12
25351 measured reflections	l = −30→29

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0885P)²] where P = (F_o² + 2F_c²)/3
4804 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 1.46 e Å⁻³
3 restraints	Δρ_min = −1.80 e Å⁻³

Crystal data top

[Hg(C₄₂H₃₈N₄O₂)](PF₆)₂·2C₂H₃N	V = 4687 (2) Å³
M_r = 1203.4	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 19.774 (5) Å	µ = 3.45 mm⁻¹
b = 9.774 (3) Å	T = 298 K
c = 24.250 (6) Å	0.24 × 0.08 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4804 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	3011 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.864	R_int = 0.086
25351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	3 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.10	Δρ_max = 1.46 e Å⁻³
4804 reflections	Δρ_min = −1.80 e Å⁻³
313 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
Hg1	0.0000	0.46027 (4)	0.2500	0.03456 (17)
N1	0.1519 (4)	0.5080 (8)	0.2447 (3)	0.0373 (17)
N2	0.1200 (3)	0.3926 (8)	0.1754 (3)	0.0378 (17)
O1	0.0679 (4)	0.7289 (7)	0.2621 (3)	0.054 (2)
C1	0.0977 (4)	0.4525 (8)	0.2209 (3)	0.0316 (18)
C2	0.2094 (5)	0.4854 (12)	0.2147 (5)	0.057 (3)
H2	0.2531	0.5141	0.2229	0.068*
C3	0.1889 (5)	0.4122 (11)	0.1705 (4)	0.052 (3)
H3	0.2162	0.3808	0.1419	0.062*
C4	0.1511 (5)	0.5826 (10)	0.2972 (4)	0.044 (2)
H4A	0.1957	0.5791	0.3136	0.053*
H4B	0.1198	0.5379	0.3222	0.053*
C5	0.1304 (5)	0.7289 (10)	0.2901 (4)	0.049 (3)
H5A	0.1258	0.7729	0.3257	0.058*
H5B	0.1641	0.7780	0.2688	0.058*
C6	0.0285 (6)	0.8505 (10)	0.2693 (4)	0.048 (2)
H6A	0.0565	0.9303	0.2628	0.057*
H6B	0.0117	0.8548	0.3068	0.057*
C7	0.0762 (5)	0.3126 (10)	0.1375 (4)	0.046 (2)
H7A	0.0425	0.3731	0.1218	0.055*
H7B	0.0527	0.2429	0.1586	0.055*
C8	0.1157 (5)	0.2431 (11)	0.0902 (4)	0.046 (2)
C9	0.1315 (5)	0.3178 (11)	0.0428 (4)	0.048 (3)
C10	0.1182 (6)	0.4599 (12)	0.0370 (5)	0.060 (3)
H10	0.0982	0.5063	0.0663	0.073*
C11	0.1334 (8)	0.5304 (11)	−0.0093 (5)	0.067 (4)
H11	0.1218	0.6223	−0.0124	0.081*
C12	0.1673 (6)	0.4629 (14)	−0.0533 (5)	0.070 (4)
H12	0.1793	0.5117	−0.0847	0.084*
C13	0.1823 (5)	0.3289 (13)	−0.0497 (4)	0.058 (3)
H13	0.2038	0.2861	−0.0791	0.069*
C14	0.1654 (5)	0.2502 (11)	−0.0012 (4)	0.050 (3)
C15	0.1800 (5)	0.1125 (12)	0.0019 (4)	0.050 (3)
H15	0.2000	0.0694	−0.0282	0.061*
C16	0.1655 (5)	0.0367 (11)	0.0488 (4)	0.048 (3)
C17	0.1790 (5)	−0.1056 (12)	0.0516 (5)	0.055 (3)
H17	0.1975	−0.1491	0.0210	0.066*
C18	0.1657 (5)	−0.1800 (12)	0.0975 (5)	0.061 (3)
H18	0.1764	−0.2725	0.0985	0.073*
C19	0.1358 (6)	−0.1179 (11)	0.1431 (5)	0.064 (3)
H19	0.1259	−0.1703	0.1741	0.076*
C20	0.1209 (6)	0.0192 (11)	0.1432 (5)	0.054 (3)
H20	0.1028	0.0592	0.1747	0.065*
C21	0.1330 (5)	0.1013 (10)	0.0953 (4)	0.041 (2)
N3	0.5038 (11)	0.1282 (19)	0.1170 (10)	0.146 (8)
C22	0.5063 (9)	0.217 (2)	0.0890 (8)	0.117 (9)
C23	0.5048 (8)	0.334 (2)	0.0493 (9)	0.145 (9)
H23A	0.4653	0.3277	0.0265	0.217*
H23B	0.5445	0.3318	0.0266	0.217*
H23C	0.5037	0.4190	0.0694	0.217*
P1	0.13116 (17)	0.1670 (3)	0.34660 (15)	0.0625 (8)
F1	0.1456 (7)	0.1821 (11)	0.4086 (4)	0.165 (5)
F2	0.1925 (4)	0.2599 (8)	0.3349 (5)	0.136 (4)
F3	0.1723 (6)	0.0382 (8)	0.3418 (7)	0.194 (7)
F4	0.0695 (5)	0.0783 (9)	0.3592 (4)	0.128 (4)
F5	0.0880 (4)	0.3006 (8)	0.3479 (5)	0.125 (3)
F6	0.1159 (9)	0.1570 (13)	0.2854 (4)	0.219 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0341 (3)	0.0382 (3)	0.0314 (2)	0.000	0.0074 (3)	0.000
N1	0.040 (4)	0.047 (4)	0.025 (4)	−0.003 (3)	0.002 (4)	−0.010 (4)
N2	0.024 (4)	0.049 (4)	0.041 (4)	0.001 (4)	0.006 (3)	−0.007 (4)
O1	0.067 (5)	0.037 (3)	0.057 (5)	−0.002 (3)	−0.013 (3)	−0.017 (3)
C1	0.039 (5)	0.034 (4)	0.022 (4)	−0.002 (4)	0.006 (4)	0.002 (4)
C2	0.029 (5)	0.081 (8)	0.061 (7)	−0.009 (5)	0.007 (5)	−0.032 (6)
C3	0.032 (5)	0.076 (7)	0.047 (6)	0.001 (5)	0.013 (5)	−0.011 (6)
C4	0.040 (6)	0.047 (5)	0.045 (6)	−0.002 (5)	−0.004 (5)	−0.004 (5)
C5	0.054 (6)	0.047 (6)	0.045 (6)	−0.009 (5)	−0.013 (5)	−0.015 (5)
C6	0.064 (6)	0.036 (5)	0.043 (5)	0.001 (5)	−0.007 (5)	−0.002 (4)
C7	0.040 (5)	0.052 (6)	0.046 (6)	−0.007 (5)	0.013 (5)	−0.013 (5)
C8	0.041 (5)	0.060 (6)	0.036 (5)	−0.010 (5)	0.005 (4)	−0.018 (5)
C9	0.037 (5)	0.060 (6)	0.048 (6)	−0.009 (5)	0.006 (5)	−0.024 (5)
C10	0.067 (8)	0.065 (7)	0.050 (7)	−0.010 (6)	0.008 (6)	−0.016 (6)
C11	0.087 (10)	0.062 (8)	0.053 (8)	−0.006 (7)	−0.002 (6)	0.005 (6)
C12	0.060 (8)	0.096 (11)	0.055 (7)	−0.007 (8)	−0.008 (6)	0.001 (7)
C13	0.061 (7)	0.077 (8)	0.035 (5)	−0.006 (7)	0.002 (5)	−0.008 (6)
C14	0.046 (6)	0.061 (6)	0.042 (6)	−0.013 (6)	0.008 (5)	−0.012 (5)
C15	0.047 (6)	0.064 (6)	0.040 (6)	0.000 (6)	0.011 (5)	−0.014 (5)
C16	0.034 (5)	0.061 (7)	0.047 (6)	−0.005 (5)	−0.003 (4)	−0.020 (5)
C17	0.040 (6)	0.061 (7)	0.065 (7)	0.000 (5)	−0.004 (5)	−0.025 (6)
C18	0.053 (7)	0.057 (7)	0.073 (8)	0.001 (6)	−0.016 (6)	−0.004 (6)
C19	0.079 (8)	0.047 (6)	0.066 (7)	−0.011 (6)	−0.009 (7)	0.000 (6)
C20	0.055 (7)	0.064 (7)	0.045 (6)	−0.020 (6)	−0.001 (5)	−0.008 (5)
C21	0.034 (5)	0.050 (5)	0.040 (5)	−0.011 (5)	0.001 (4)	−0.012 (5)
N3	0.114 (13)	0.110 (13)	0.21 (2)	0.013 (13)	−0.025 (13)	−0.071 (16)
C22	0.044 (9)	0.124 (17)	0.18 (3)	0.015 (15)	−0.002 (14)	−0.085 (18)
C23	0.097 (14)	0.16 (2)	0.18 (2)	0.033 (15)	0.064 (13)	−0.022 (18)
P1	0.068 (2)	0.0389 (14)	0.080 (2)	−0.0070 (15)	−0.0066 (18)	−0.0066 (15)
F1	0.258 (14)	0.134 (8)	0.103 (7)	−0.033 (9)	−0.075 (8)	−0.014 (7)
F2	0.091 (6)	0.088 (6)	0.228 (12)	−0.023 (5)	0.030 (7)	0.004 (7)
F3	0.179 (11)	0.056 (5)	0.35 (2)	0.026 (6)	0.102 (12)	−0.006 (8)
F4	0.108 (7)	0.121 (7)	0.155 (9)	−0.050 (6)	0.032 (6)	−0.023 (7)
F5	0.078 (5)	0.089 (6)	0.208 (11)	0.011 (5)	0.000 (6)	0.024 (7)
F6	0.42 (2)	0.158 (11)	0.084 (7)	−0.145 (14)	−0.030 (10)	−0.001 (7)

Geometric parameters (Å, º) top

Hg1—C1	2.058 (9)	C11—C12	1.423 (17)
Hg1—C1ⁱ	2.058 (9)	C11—H11	0.9300
N1—C1	1.334 (11)	C12—C13	1.345 (15)
N1—C2	1.367 (12)	C12—H12	0.9300
N1—C4	1.466 (11)	C13—C14	1.446 (14)
N2—C1	1.324 (10)	C13—H13	0.9300
N2—C3	1.380 (11)	C14—C15	1.378 (14)
N2—C7	1.485 (11)	C15—C16	1.388 (14)
O1—C5	1.410 (11)	C15—H15	0.9300
O1—C6	1.432 (12)	C16—C17	1.417 (15)
C2—C3	1.351 (14)	C16—C21	1.444 (13)
C2—H2	0.9300	C17—C18	1.355 (15)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.497 (13)	C18—C19	1.393 (15)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.371 (15)
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—C21	1.431 (14)
C6—C6ⁱ	1.46 (2)	C20—H20	0.9300
C6—H6A	0.9700	N3—C22	1.104 (8)
C6—H6B	0.9700	C22—C23	1.497 (8)
C7—C8	1.546 (12)	C23—H23A	0.9600
C7—H7A	0.9700	C23—H23B	0.9600
C7—H7B	0.9700	C23—H23C	0.9600
C8—C9	1.397 (14)	P1—F6	1.518 (11)
C8—C21	1.433 (14)	P1—F3	1.503 (9)
C9—C10	1.421 (14)	P1—F4	1.527 (8)
C9—C14	1.422 (13)	P1—F1	1.539 (10)
C10—C11	1.352 (16)	P1—F2	1.540 (8)
C10—H10	0.9300	P1—F5	1.561 (8)

C1—Hg1—C1ⁱ	175.8 (5)	C13—C12—C11	120.5 (12)
C1—N1—C2	111.9 (7)	C13—C12—H12	119.8
C1—N1—C4	124.6 (7)	C11—C12—H12	119.8
C2—N1—C4	123.5 (8)	C12—C13—C14	121.4 (11)
C1—N2—C3	109.9 (8)	C12—C13—H13	119.3
C1—N2—C7	123.6 (7)	C14—C13—H13	119.3
C3—N2—C7	126.5 (7)	C15—C14—C9	120.8 (10)
C5—O1—C6	114.7 (7)	C15—C14—C13	121.0 (10)
N2—C1—N1	105.8 (8)	C9—C14—C13	118.1 (10)
N2—C1—Hg1	128.0 (7)	C14—C15—C16	121.5 (9)
N1—C1—Hg1	126.3 (6)	C14—C15—H15	119.3
C3—C2—N1	105.0 (9)	C16—C15—H15	119.3
C3—C2—H2	127.5	C15—C16—C17	121.6 (10)
N1—C2—H2	127.5	C15—C16—C21	119.9 (10)
C2—C3—N2	107.5 (8)	C17—C16—C21	118.4 (10)
C2—C3—H3	126.3	C18—C17—C16	121.9 (10)
N2—C3—H3	126.3	C18—C17—H17	119.0
N1—C4—C5	112.2 (8)	C16—C17—H17	119.0
N1—C4—H4A	109.2	C17—C18—C19	120.1 (11)
C5—C4—H4A	109.2	C17—C18—H18	120.0
N1—C4—H4B	109.2	C19—C18—H18	120.0
C5—C4—H4B	109.2	C20—C19—C18	121.1 (11)
H4A—C4—H4B	107.9	C20—C19—H19	119.4
O1—C5—C4	107.1 (8)	C18—C19—H19	119.4
O1—C5—H5A	110.3	C19—C20—C21	120.8 (10)
C4—C5—H5A	110.3	C19—C20—H20	119.6
O1—C5—H5B	110.3	C21—C20—H20	119.6
C4—C5—H5B	110.3	C20—C21—C8	125.0 (9)
H5A—C5—H5B	108.5	C20—C21—C16	117.5 (10)
O1—C6—C6ⁱ	110.0 (7)	C8—C21—C16	117.5 (9)
O1—C6—H6A	109.7	N3—C22—C23	176 (3)
C6ⁱ—C6—H6A	109.7	C22—C23—H23A	109.5
O1—C6—H6B	109.7	C22—C23—H23B	109.5
C6ⁱ—C6—H6B	109.7	H23A—C23—H23B	109.5
H6A—C6—H6B	108.2	C22—C23—H23C	109.5
N2—C7—C8	113.3 (7)	H23A—C23—H23C	109.5
N2—C7—H7A	108.9	H23B—C23—H23C	109.5
C8—C7—H7A	108.9	F6—P1—F3	88.8 (9)
N2—C7—H7B	108.9	F6—P1—F4	90.0 (7)
C8—C7—H7B	108.9	F3—P1—F4	88.4 (6)
H7A—C7—H7B	107.7	F6—P1—F1	178.0 (8)
C9—C8—C21	121.6 (9)	F3—P1—F1	93.2 (8)
C9—C8—C7	119.6 (9)	F4—P1—F1	90.4 (6)
C21—C8—C7	118.7 (9)	F6—P1—F2	90.9 (7)
C8—C9—C10	123.4 (9)	F3—P1—F2	93.1 (5)
C8—C9—C14	118.6 (10)	F4—P1—F2	178.3 (6)
C10—C9—C14	117.9 (10)	F1—P1—F2	88.7 (7)
C11—C10—C9	122.6 (11)	F6—P1—F5	88.0 (8)
C11—C10—H10	118.7	F3—P1—F5	176.8 (9)
C9—C10—H10	118.7	F4—P1—F5	92.0 (5)
C10—C11—C12	119.4 (11)	F1—P1—F5	90.0 (6)
C10—C11—H11	120.3	F2—P1—F5	86.6 (5)
C12—C11—H11	120.3

C3—N2—C1—N1	−0.7 (10)	C9—C10—C11—C12	−3.4 (18)
C7—N2—C1—N1	177.2 (8)	C10—C11—C12—C13	2.1 (19)
C3—N2—C1—Hg1	179.4 (7)	C11—C12—C13—C14	−1.0 (18)
C7—N2—C1—Hg1	−2.7 (13)	C8—C9—C14—C15	2.8 (15)
C2—N1—C1—N2	0.5 (11)	C10—C9—C14—C15	179.9 (10)
C4—N1—C1—N2	−178.5 (8)	C8—C9—C14—C13	−179.2 (9)
C2—N1—C1—Hg1	−179.6 (8)	C10—C9—C14—C13	−2.1 (14)
C4—N1—C1—Hg1	1.4 (13)	C12—C13—C14—C15	179.0 (11)
C1—N1—C2—C3	−0.1 (13)	C12—C13—C14—C9	1.0 (16)
C4—N1—C2—C3	178.9 (9)	C9—C14—C15—C16	−3.6 (16)
N1—C2—C3—N2	−0.3 (13)	C13—C14—C15—C16	178.5 (10)
C1—N2—C3—C2	0.6 (12)	C14—C15—C16—C17	178.5 (10)
C7—N2—C3—C2	−177.2 (10)	C14—C15—C16—C21	1.6 (15)
C1—N1—C4—C5	−82.8 (11)	C15—C16—C17—C18	179.3 (10)
C2—N1—C4—C5	98.3 (11)	C21—C16—C17—C18	−3.7 (15)
C6—O1—C5—C4	157.9 (9)	C16—C17—C18—C19	2.1 (16)
N1—C4—C5—O1	54.2 (11)	C17—C18—C19—C20	−1.6 (17)
C5—O1—C6—C6ⁱ	169.4 (10)	C18—C19—C20—C21	2.7 (16)
C1—N2—C7—C8	−175.1 (8)	C19—C20—C21—C8	176.4 (10)
C3—N2—C7—C8	2.4 (14)	C19—C20—C21—C16	−4.3 (14)
N2—C7—C8—C9	−83.4 (11)	C9—C8—C21—C20	177.5 (9)
N2—C7—C8—C21	99.1 (10)	C7—C8—C21—C20	−5.0 (14)
C21—C8—C9—C10	−177.0 (10)	C9—C8—C21—C16	−1.8 (14)
C7—C8—C9—C10	5.6 (15)	C7—C8—C21—C16	175.7 (8)
C21—C8—C9—C14	0.0 (14)	C15—C16—C21—C20	−178.3 (9)
C7—C8—C9—C14	−177.5 (8)	C17—C16—C21—C20	4.7 (13)
C8—C9—C10—C11	−179.6 (11)	C15—C16—C21—C8	1.1 (13)
C14—C9—C10—C11	3.4 (17)	C17—C16—C21—C8	−175.9 (8)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···F5	0.97	2.48	3.265 (13)	137

Experimental details

Crystal data
Chemical formula	[Hg(C₄₂H₃₈N₄O₂)](PF₆)₂·2C₂H₃N
M_r	1203.4
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	19.774 (5), 9.774 (3), 24.250 (6)
V (Å³)	4687 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.45
Crystal size (mm)	0.24 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.775, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	25351, 4804, 3011
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.169, 1.10
No. of reflections	4804
No. of parameters	313
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.46, −1.80

Computer programs: APEX2 (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Hg1—C1

2.058 (9)

P1—F5

1.561 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···F5	0.97	2.48	3.265 (13)	137

Acknowledgements

We acknowledge financial support from the Research Fund for the Education Department of Shanxi Province (No. 2010111) and the financial support from the Opening Foundation of Key Laboratory of Shanxi Province (No. 2009011059-7) and the Shanxi Natural Science Foundation of China (Nos 2006011069 and 2011011006-4).

References

Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, W.-Y. & Dong, G.-Y. (2009). Acta Cryst. E65, m217. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nielsen, D. J., Cavell, K. J., Skelton, B. W. & White, A. H. (2006). Organometallics, 25, 4850–4856. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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

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

{3,3′-Bis[(anthracen-9-yl)meth­yl]-1,1′-[(ethane-1,2-diyldi­­oxy)bis­­(ethane-1,2-di­yl)]bis­­(imidazol-2-yl­­idene)}mercury(II) bis­­(hexa­fluoridophosphate) aceto­nitrile disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{3,3′-Bis[(anthracen-9-yl)methyl]-1,1′-[(ethane-1,2-diyldioxy)bis(ethane-1,2-diyl)]bis(imidazol-2-ylidene)}mercury(II) bis(hexafluoridophosphate) acetonitrile disolvate