{3,3'-Bis[(anthracen-9-yl)meth-yl]-1,1'-[(ethane-1,2-diyldi-oxy)bis-(ethane-1,2-di-yl)]bis-(imidazol-2-yl-idene)}mercury(II) bis-(hexa-fluoridophosphate) acetonitrile disolvate.

In the title compound, [Hg(C(42)H(38)N(4)O(2))](PF(6))(2)·2CH(3)CN, the Hg(II) cation lies on a twofold axis which is also the inter-nal 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 inter-molecular C-H⋯F inter-actions in the crystal packing between an F atom of a hexa-fluoridophosphate anion and a -CH(2)- 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 = 1203.4

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.169

S = 1.10

4804 reflections

313 parameters

3 restraints

H-atom parameters constrained

Δρmax = 1.46 e Å−3

Δρmin = −1.80 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005958/vn2031sup1.cif

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

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

[Hg(C42H38N4O2)](PF6)2·2C2H3N	F(000) = 2384
Mr = 1203.4	Dx = 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

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

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(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3
4804 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 1.46 e Å−3
3 restraints	Δρmin = −1.80 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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