[3,3′-Bis(1-naphthylmethyl)-1,1′-(2,2′-oxy­diethyl­ene)bis­(imidazol-2-yl­idene)]mercury(II) bis­(hexa­fluorido­phosphate) acetonitrile solvate

Guo, W.-Y.; Dong, G.-Y.

doi:10.1107/S1600536809001743

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m217

doi:10.1107/S1600536809001743

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[3,3′-Bis(1-naphthylmethyl)-1,1′-(2,2′-oxydiethylene)bis(imidazol-2-ylidene)]mercury(II) bis(hexafluoridophosphate) acetonitrile solvate

Wen-Yan Guo ^a ^* and Gui-Ying Dong ^b

^aDepartment of Chemistry, Shanxi Normal University, Linfen 041004, People's Republic of China, and ^bCollege of Chemical Engineering and Biotechnology, Hebei Polytechnic University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: guowenyan2008@yahoo.com.cn

(Received 26 December 2008; accepted 14 January 2009; online 23 January 2009)

In the title compound, [Hg(C₃₂H₃₀N₄O)](PF₆)₂·CH₃CN, the mercury(II) ion is coordinated by two carbene C atoms [Hg—C = 2.060 (6) and 2.066 (6) Å] and one ether O atom [Hg—O = 2.561 (5) Å] in a distorted T-shaped geometry with a C—Hg—C angle of 166.3 (3)°. One hexafluoridophosphate anion is rotationally disordered between two orientations with an approximate ratio of 2:1. The crystal packing exhibits weak intermolecular C—H⋯F and C—H⋯N interactions.

Related literature

For the crystal structures of related silver, gold and palladium complexes, see: Wang et al. (2005 ); Nielsen et al. (2006 ). For the details of synthesis of nucleophilic heterocyclic carbene ligands, see: Arduengo et al. (1991 ); Wang et al. (2006 ).

Experimental

Crystal data

[Hg(C₃₂H₃₀N4O)](PF₆)₂·C₂H₃N
M_r = 1018.18
Monoclinic, P 2₁ /n
a = 9.204 (2) Å
b = 11.433 (3) Å
c = 35.922 (10) Å
β = 92.837 (5)°
V = 3775.7 (17) Å³
Z = 4
Mo Kα radiation
μ = 4.26 mm⁻¹
T = 293 (2) K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.448, T_max = 0.590
21427 measured reflections
7729 independent reflections
5450 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.101
S = 1.12
7729 reflections
552 parameters
108 restraints
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −1.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯F3	0.97	2.50	3.384 (9)	151
C5—H5B⋯F7	0.97	2.39	3.307 (9)	157
C18—H18A⋯F4ⁱ	0.97	2.53	3.150 (10)	122
C22—H22B⋯F9ⁱⁱ	0.97	2.46	3.195 (11)	132
C24—H24⋯N4	0.93	2.50	2.847 (9)	103
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y-1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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/S1600536809001743/cv2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001743/cv2505Isup2.hkl

checkCIF report

Comment top

Nucleophilic heterocyclic carbene (NHC) ligands have enjoyed wide applicability as ligands for transition metals in a variety of catalytic transformations since they were first isolated in 1991 (Arduengo et al., 1991).The silver, gold and palladium complexes of bis-NHC ligands bearing a weakly coordinating ether functionality have been reported (Wang et al., 2005; Nielsen et al., 2006). To study further the coordination chemistry of this ligand, we report here the crystal structure of the title complex, (I).

The title compound, [Hg(C₃₂H₃₀N₄O)](PF₆)₂[CH₃CN] (I), crystallizes with one (R)-2,2'-bis[1H-imidazole-3-oxyethyl-1-(1-menaphthyl)]-1,1'-binaphthyl mercury (II) cation, two hexafluoridophosphate anions and one acetonitrile solvate molecule in an asymmetric unit. The cation of (I) is a 10-membered macrocyclic metal complex of naphthyl-carbene ligand adopting a cis-conformation. The geometry of the Hg(II) coordination is distorted T-shaped, formed by two C(carbene) atoms [Hg—C = 2.060 (6) and 2.066 (6) Å] and one ether oxygen atom with bond angle C2—Hg1—O1=83.6 (2)°, C1—Hg1—O1= 82.9 (2)° and C1—Hg1—C2=166.3 (3)°,respectively. The crystal packing exhibits weak intermolecular C—H···F and C—H···N interactions (Table 1).

Related literature top

For the crystal structures of related silver, gold and palladium complexes, see: Wang et al. (2005); Nielsen et al. (2006). For the details of synthesis of nucleophilic heterocyclic carbene ligands, see: Arduengo et al. (1991); Wang et al. (2006).

Experimental top

The ligand 1,1'-(oxy-1,2-ethanediyl)bis[3-(1-naphthalenemethyl)imidazolium bis(hexafluoridophosphate) was prepared according to the reported procedure (Wang et al., 2006). Anhydrous Hg(OAc)₂ (29.5 mg, 0.10 mmol) was added to a solution of the corresponding diazolium salt (77.0 mg, 0.10 mmol) in acetonitrile (25 ml) under argon. The mixture was refluxed for 12 h and then cooled to the room temperature. the acetonitrile was removed in vacuo to give a white solid which was washed with methanol to give the crude product. White single crystals of the title compound were obtained by recrystallization from acetonitile and ethyl ether (yield: 90%) Anal. Calcd. for C₃₄H₃₃F₁₂HgN₅OP₂: C, 40.11; H, 3.27; N, 6.88 Found: C, 40.10; H, 3.22; N 6.85

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 cation in (I) showing the atomic numbering and 30% probability displacement ellipsoids.

[3,3'-Bis(1-naphthylmethyl)-1,1'-(2,2'-oxydiethylene)bis(imidazol-2- ylidene)]mercury(II) bis(hexafluoridophosphate) acetonitrile solvate top

Crystal data top

[Hg(C₃₂H₃₀N4O)](PF₆)₂·C₂H₃N	F(000) = 1992
M_r = 1018.18	D_x = 1.791 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.204 (2) Å	Cell parameters from 857 reflections
b = 11.433 (3) Å	θ = 2.3–22.3°
c = 35.922 (10) Å	µ = 4.26 mm⁻¹
β = 92.837 (5)°	T = 293 K
V = 3775.7 (17) Å³	Block, white
Z = 4	0.18 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7729 independent reflections
Radiation source: fine-focus sealed tube	5450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.448, T_max = 0.590	k = −14→13
21427 measured reflections	l = −44→28

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0346P)² + 0.5948P] where P = (F_o² + 2F_c²)/3
7729 reflections	(Δ/σ)_max = 0.001
552 parameters	Δρ_max = 0.82 e Å⁻³
108 restraints	Δρ_min = −1.46 e Å⁻³

Crystal data top

[Hg(C₃₂H₃₀N4O)](PF₆)₂·C₂H₃N	V = 3775.7 (17) Å³
M_r = 1018.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.204 (2) Å	µ = 4.26 mm⁻¹
b = 11.433 (3) Å	T = 293 K
c = 35.922 (10) Å	0.18 × 0.16 × 0.12 mm
β = 92.837 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7729 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5450 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.590	R_int = 0.062
21427 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	108 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.12	Δρ_max = 0.82 e Å⁻³
7729 reflections	Δρ_min = −1.46 e Å⁻³
552 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	Occ. (<1)
Hg1	0.78607 (3)	0.22825 (2)	0.087425 (8)	0.04048 (10)
N1	0.6181 (6)	0.4642 (5)	0.09040 (16)	0.0405 (14)
N2	0.7257 (6)	0.4380 (5)	0.03912 (17)	0.0446 (14)
N3	0.8152 (6)	−0.0190 (5)	0.06247 (17)	0.0456 (15)
N4	0.9815 (6)	0.0114 (4)	0.10573 (16)	0.0400 (14)
O1	0.7511 (5)	0.1912 (4)	0.01725 (14)	0.0562 (14)
C1	0.7067 (7)	0.3919 (6)	0.07289 (18)	0.0356 (15)
C2	0.8659 (7)	0.0599 (5)	0.08832 (19)	0.0364 (16)
C3	0.5818 (8)	0.5568 (6)	0.0675 (2)	0.053 (2)
H3	0.5218	0.6193	0.0730	0.063*
C4	0.6487 (8)	0.5400 (6)	0.0362 (2)	0.055 (2)
H4	0.6439	0.5894	0.0156	0.066*
C5	0.5474 (7)	0.4420 (6)	0.1255 (2)	0.0472 (18)
H5A	0.4552	0.4033	0.1198	0.057*
H5B	0.5264	0.5167	0.1369	0.057*
C6	0.6331 (7)	0.3695 (6)	0.15335 (19)	0.0401 (16)
C7	0.5962 (8)	0.2543 (6)	0.1577 (2)	0.0507 (19)
H7	0.5226	0.2219	0.1423	0.061*
C8	0.6666 (9)	0.1856 (7)	0.1845 (2)	0.059 (2)
H8	0.6406	0.1074	0.1868	0.071*
C9	0.7719 (9)	0.2303 (8)	0.2072 (2)	0.064 (2)
H9	0.8177	0.1824	0.2251	0.077*
C10	0.8150 (7)	0.3472 (7)	0.2046 (2)	0.051 (2)
C11	0.7459 (7)	0.4197 (6)	0.1767 (2)	0.0437 (17)
C12	0.7841 (8)	0.5398 (7)	0.1752 (3)	0.062 (2)
H12	0.7393	0.5886	0.1574	0.075*
C13	0.8879 (10)	0.5835 (9)	0.2004 (3)	0.083 (3)
H13	0.9133	0.6621	0.1993	0.100*
C14	0.9563 (11)	0.5114 (11)	0.2276 (3)	0.093 (4)
H14	1.0252	0.5429	0.2446	0.111*
C15	0.9225 (9)	0.3971 (10)	0.2293 (3)	0.077 (3)
H15	0.9707	0.3499	0.2471	0.093*
C16	0.8153 (8)	0.3898 (7)	0.0104 (2)	0.056 (2)
H16A	0.9099	0.3698	0.0218	0.068*
H16B	0.8301	0.4498	−0.0081	0.068*
C17	0.7529 (10)	0.2839 (7)	−0.0088 (2)	0.065 (2)
H17A	0.6549	0.3001	−0.0186	0.077*
H17B	0.8116	0.2625	−0.0294	0.077*
C18	0.7271 (9)	0.0771 (7)	0.0039 (2)	0.063 (2)
H18A	0.8134	0.0488	−0.0076	0.076*
H18B	0.6473	0.0771	−0.0148	0.076*
C19	0.6917 (8)	−0.0015 (7)	0.0353 (3)	0.066 (3)
H19A	0.6106	0.0314	0.0480	0.080*
H19B	0.6612	−0.0769	0.0252	0.080*
C20	0.8994 (8)	−0.1176 (6)	0.0652 (2)	0.058 (2)
H20	0.8875	−0.1850	0.0509	0.069*
C21	1.0027 (8)	−0.0991 (6)	0.0926 (2)	0.052 (2)
H21	1.0745	−0.1515	0.1009	0.062*
C22	1.0724 (7)	0.0685 (5)	0.13471 (18)	0.0384 (16)
H22A	1.0608	0.1525	0.1320	0.046*
H22B	1.1733	0.0502	0.1307	0.046*
C23	1.0407 (7)	0.0353 (6)	0.1741 (2)	0.0405 (17)
C24	0.9391 (8)	−0.0466 (6)	0.1815 (2)	0.052 (2)
H24	0.8897	−0.0861	0.1621	0.063*
C25	0.9092 (10)	−0.0711 (7)	0.2189 (3)	0.068 (3)
H25	0.8407	−0.1281	0.2238	0.082*
C26	0.9761 (10)	−0.0150 (8)	0.2475 (3)	0.072 (3)
H26	0.9535	−0.0326	0.2718	0.087*
C27	1.0806 (9)	0.0706 (8)	0.2406 (2)	0.060 (2)
C28	1.1169 (7)	0.0954 (6)	0.2036 (2)	0.0460 (18)
C29	1.2233 (8)	0.1818 (7)	0.1976 (2)	0.060 (2)
H29	1.2519	0.1968	0.1736	0.072*
C30	1.2843 (9)	0.2434 (8)	0.2272 (3)	0.079 (3)
H30	1.3532	0.3006	0.2229	0.095*
C31	1.2465 (12)	0.2229 (11)	0.2629 (3)	0.099 (4)
H31	1.2874	0.2675	0.2824	0.118*
C32	1.1476 (11)	0.1357 (10)	0.2701 (3)	0.086 (3)
H32	1.1251	0.1199	0.2946	0.103*
P1	0.2485 (2)	0.25046 (17)	0.05306 (6)	0.0565 (6)
F1	0.0984 (6)	0.2867 (5)	0.07142 (18)	0.1065 (19)
F2	0.2972 (6)	0.3825 (4)	0.05426 (15)	0.0916 (17)
F3	0.3110 (7)	0.2339 (5)	0.09374 (17)	0.121 (2)
F4	0.1948 (7)	0.1215 (4)	0.05251 (18)	0.121 (2)
F5	0.1711 (8)	0.2736 (6)	0.01355 (16)	0.126 (2)
F6	0.3852 (7)	0.2175 (6)	0.0336 (3)	0.168 (4)
P2	0.4756 (3)	0.85219 (19)	0.12903 (7)	0.0684 (7)
F7	0.4630 (11)	0.7192 (5)	0.1395 (2)	0.098 (4)	0.676 (17)
F8	0.5350 (14)	0.8758 (9)	0.1705 (2)	0.142 (6)	0.676 (17)
F9	0.3183 (8)	0.8715 (10)	0.1421 (4)	0.160 (7)	0.676 (17)
F10	0.4176 (16)	0.8252 (9)	0.0891 (2)	0.162 (7)	0.676 (17)
F11	0.6340 (8)	0.8292 (11)	0.1181 (4)	0.167 (7)	0.676 (17)
F12	0.4887 (16)	0.9829 (5)	0.1198 (3)	0.170 (7)	0.676 (17)
F7'	0.580 (2)	0.779 (2)	0.1544 (7)	0.25 (2)	0.324 (17)
F8'	0.390 (3)	0.8943 (16)	0.1622 (5)	0.136 (12)	0.324 (17)
F9'	0.372 (2)	0.7449 (17)	0.1231 (6)	0.213 (19)	0.324 (17)
F10'	0.558 (2)	0.8116 (14)	0.0936 (5)	0.118 (11)	0.324 (17)
F11'	0.579 (2)	0.9594 (16)	0.1324 (6)	0.137 (12)	0.324 (17)
F12'	0.370 (2)	0.925 (2)	0.1017 (6)	0.154 (13)	0.324 (17)
N5	−0.0008 (12)	0.5965 (9)	0.0750 (3)	0.119 (4)
C33	0.0674 (11)	0.5635 (10)	0.1002 (4)	0.093 (4)
C34	0.1418 (12)	0.5175 (13)	0.1326 (4)	0.151 (6)
H34A	0.1599	0.5791	0.1503	0.226*
H34B	0.2326	0.4841	0.1259	0.226*
H34C	0.0831	0.4582	0.1433	0.226*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.04380 (15)	0.03932 (15)	0.03823 (15)	0.00852 (13)	0.00125 (10)	0.00183 (15)
N1	0.042 (3)	0.040 (3)	0.040 (4)	0.007 (3)	0.000 (3)	0.001 (3)
N2	0.053 (4)	0.043 (3)	0.038 (4)	0.002 (3)	0.002 (3)	0.010 (3)
N3	0.047 (3)	0.045 (4)	0.044 (4)	0.002 (3)	−0.001 (3)	−0.006 (3)
N4	0.039 (3)	0.036 (3)	0.045 (4)	0.004 (2)	0.000 (3)	0.002 (3)
O1	0.080 (4)	0.049 (3)	0.038 (3)	0.005 (3)	−0.003 (3)	−0.004 (2)
C1	0.038 (4)	0.045 (4)	0.023 (4)	0.004 (3)	−0.006 (3)	0.006 (3)
C2	0.036 (4)	0.035 (4)	0.038 (4)	−0.001 (3)	0.003 (3)	0.004 (3)
C3	0.064 (5)	0.038 (4)	0.055 (5)	0.011 (3)	0.004 (4)	0.012 (4)
C4	0.067 (5)	0.052 (5)	0.047 (5)	0.009 (4)	0.004 (4)	0.020 (4)
C5	0.045 (4)	0.045 (4)	0.052 (5)	0.015 (3)	0.007 (4)	−0.005 (4)
C6	0.040 (4)	0.047 (4)	0.034 (4)	0.013 (3)	0.006 (3)	−0.003 (3)
C7	0.058 (4)	0.043 (5)	0.051 (5)	−0.002 (3)	0.012 (4)	−0.007 (4)
C8	0.071 (5)	0.043 (4)	0.065 (6)	0.005 (4)	0.013 (5)	0.006 (4)
C9	0.062 (5)	0.069 (6)	0.062 (6)	0.029 (5)	0.015 (4)	0.019 (5)
C10	0.034 (4)	0.076 (6)	0.043 (5)	0.015 (4)	0.001 (3)	−0.004 (4)
C11	0.045 (4)	0.053 (5)	0.034 (4)	0.010 (3)	0.010 (3)	−0.002 (4)
C12	0.061 (5)	0.055 (5)	0.071 (6)	−0.003 (4)	0.009 (5)	−0.006 (5)
C13	0.070 (6)	0.085 (7)	0.096 (9)	−0.028 (5)	0.020 (6)	−0.039 (6)
C14	0.073 (7)	0.138 (10)	0.065 (8)	−0.012 (7)	−0.010 (6)	−0.047 (7)
C15	0.059 (6)	0.112 (8)	0.060 (6)	0.017 (5)	−0.006 (5)	−0.019 (6)
C16	0.061 (5)	0.058 (5)	0.051 (5)	0.002 (4)	0.014 (4)	0.018 (4)
C17	0.085 (6)	0.070 (6)	0.039 (5)	0.025 (5)	0.006 (4)	0.010 (5)
C18	0.072 (6)	0.063 (6)	0.053 (6)	0.004 (4)	−0.020 (5)	−0.009 (5)
C19	0.057 (5)	0.057 (5)	0.083 (7)	−0.001 (4)	−0.021 (5)	−0.016 (5)
C20	0.069 (5)	0.039 (4)	0.065 (6)	0.009 (4)	0.000 (5)	−0.013 (4)
C21	0.060 (5)	0.038 (4)	0.057 (5)	0.015 (3)	−0.003 (4)	−0.004 (4)
C22	0.039 (4)	0.040 (4)	0.036 (4)	0.003 (3)	−0.002 (3)	0.002 (3)
C23	0.045 (4)	0.036 (4)	0.042 (4)	0.011 (3)	0.011 (3)	0.014 (3)
C24	0.054 (5)	0.047 (4)	0.056 (5)	0.012 (4)	0.011 (4)	0.010 (4)
C25	0.075 (6)	0.061 (6)	0.070 (7)	0.013 (4)	0.025 (5)	0.024 (5)
C26	0.083 (7)	0.096 (7)	0.041 (6)	0.033 (6)	0.024 (5)	0.031 (5)
C27	0.057 (5)	0.090 (6)	0.035 (5)	0.035 (5)	0.011 (4)	0.010 (5)
C28	0.037 (4)	0.062 (5)	0.039 (5)	0.016 (3)	0.001 (3)	0.001 (4)
C29	0.046 (4)	0.081 (6)	0.052 (5)	−0.001 (4)	0.001 (4)	−0.008 (5)
C30	0.061 (5)	0.101 (7)	0.074 (7)	0.006 (5)	−0.015 (5)	−0.031 (6)
C31	0.086 (7)	0.149 (11)	0.058 (7)	0.038 (7)	−0.028 (6)	−0.054 (7)
C32	0.081 (7)	0.142 (10)	0.034 (5)	0.047 (7)	0.001 (5)	−0.001 (6)
P1	0.0708 (13)	0.0512 (15)	0.0477 (12)	−0.0113 (10)	0.0043 (10)	0.0032 (10)
F1	0.093 (4)	0.110 (4)	0.119 (5)	0.002 (3)	0.026 (4)	0.010 (4)
F2	0.134 (5)	0.059 (3)	0.081 (4)	−0.030 (3)	−0.003 (3)	0.009 (3)
F3	0.151 (6)	0.117 (5)	0.088 (5)	−0.046 (4)	−0.053 (4)	0.043 (4)
F4	0.188 (6)	0.060 (3)	0.120 (5)	−0.041 (4)	0.051 (5)	−0.020 (3)
F5	0.150 (6)	0.161 (6)	0.066 (4)	−0.056 (4)	−0.020 (4)	0.025 (4)
F6	0.110 (5)	0.127 (5)	0.277 (11)	0.016 (4)	0.108 (6)	0.001 (6)
P2	0.0722 (15)	0.0515 (15)	0.0814 (19)	0.0090 (11)	0.0026 (14)	−0.0021 (13)
F7	0.128 (9)	0.046 (5)	0.121 (9)	0.015 (5)	0.034 (7)	−0.006 (5)
F8	0.202 (15)	0.134 (10)	0.085 (8)	−0.020 (9)	−0.058 (9)	−0.010 (7)
F9	0.091 (8)	0.187 (13)	0.202 (17)	0.079 (8)	−0.004 (9)	−0.024 (12)
F10	0.267 (19)	0.130 (10)	0.080 (8)	0.018 (12)	−0.080 (10)	−0.015 (7)
F11	0.083 (8)	0.218 (16)	0.204 (17)	−0.027 (8)	0.053 (9)	0.003 (13)
F12	0.32 (2)	0.051 (6)	0.136 (11)	−0.031 (8)	−0.061 (12)	0.013 (6)
F7'	0.21 (3)	0.21 (3)	0.32 (4)	0.08 (3)	−0.04 (3)	0.11 (3)
F8'	0.15 (2)	0.16 (2)	0.10 (2)	0.067 (19)	0.042 (18)	−0.009 (16)
F9'	0.16 (3)	0.18 (3)	0.31 (4)	−0.11 (2)	0.05 (3)	0.01 (3)
F10'	0.113 (18)	0.072 (13)	0.18 (3)	−0.033 (13)	0.078 (17)	−0.066 (15)
F11'	0.14 (2)	0.16 (2)	0.11 (2)	−0.084 (18)	−0.024 (16)	−0.043 (17)
F12'	0.128 (19)	0.19 (3)	0.14 (2)	0.061 (19)	−0.023 (17)	0.02 (2)
N5	0.136 (9)	0.095 (7)	0.127 (10)	0.007 (7)	0.004 (8)	−0.008 (7)
C33	0.060 (7)	0.101 (9)	0.117 (11)	0.010 (6)	−0.003 (7)	−0.043 (8)
C34	0.081 (8)	0.253 (17)	0.116 (12)	0.056 (10)	−0.013 (8)	−0.055 (12)

Geometric parameters (Å, º) top

Hg1—C2	2.060 (6)	C19—H19A	0.9700
Hg1—C1	2.066 (6)	C19—H19B	0.9700
Hg1—O1	2.561 (5)	C20—C21	1.349 (10)
N1—C1	1.340 (8)	C20—H20	0.9300
N1—C3	1.371 (8)	C21—H21	0.9300
N1—C5	1.471 (9)	C22—C23	1.508 (9)
N2—C1	1.342 (8)	C22—H22A	0.9700
N2—C4	1.366 (8)	C22—H22B	0.9700
N2—C16	1.459 (9)	C23—C24	1.358 (9)
N3—C2	1.360 (8)	C23—C28	1.419 (10)
N3—C20	1.369 (8)	C24—C25	1.413 (11)
N3—C19	1.476 (9)	C24—H24	0.9300
N4—C2	1.328 (8)	C25—C26	1.335 (12)
N4—C21	1.366 (8)	C25—H25	0.9300
N4—C22	1.458 (8)	C26—C27	1.403 (12)
O1—C18	1.403 (8)	C26—H26	0.9300
O1—C17	1.414 (8)	C27—C32	1.412 (12)
C3—C4	1.324 (10)	C27—C28	1.416 (10)
C3—H3	0.9300	C28—C29	1.415 (10)
C4—H4	0.9300	C29—C30	1.374 (11)
C5—C6	1.494 (9)	C29—H29	0.9300
C5—H5A	0.9700	C30—C31	1.365 (14)
C5—H5B	0.9700	C30—H30	0.9300
C6—C7	1.370 (9)	C31—C32	1.383 (14)
C6—C11	1.423 (9)	C31—H31	0.9300
C7—C8	1.379 (10)	C32—H32	0.9300
C7—H7	0.9300	P1—F6	1.516 (6)
C8—C9	1.336 (11)	P1—F4	1.555 (5)
C8—H8	0.9300	P1—F3	1.555 (6)
C9—C10	1.399 (11)	P1—F2	1.575 (5)
C9—H9	0.9300	P1—F5	1.579 (6)
C10—C15	1.416 (11)	P1—F1	1.614 (6)
C10—C11	1.427 (10)	P2—F8'	1.536 (8)
C11—C12	1.419 (10)	P2—F12	1.537 (6)
C12—C13	1.377 (11)	P2—F10	1.538 (6)
C12—H12	0.9300	P2—F7'	1.539 (8)
C13—C14	1.405 (14)	P2—F11	1.551 (6)
C13—H13	0.9300	P2—F11'	1.555 (8)
C14—C15	1.346 (13)	P2—F9	1.560 (7)
C14—H14	0.9300	P2—F9'	1.561 (8)
C15—H15	0.9300	P2—F7	1.572 (6)
C16—C17	1.495 (10)	P2—F10'	1.582 (8)
C16—H16A	0.9700	P2—F12'	1.585 (8)
C16—H16B	0.9700	P2—F8	1.585 (6)
C17—H17A	0.9700	N5—C33	1.141 (13)
C17—H17B	0.9700	C33—C34	1.421 (16)
C18—C19	1.489 (11)	C34—H34A	0.9600
C18—H18A	0.9700	C34—H34B	0.9600
C18—H18B	0.9700	C34—H34C	0.9600

C2—Hg1—C1	166.3 (3)	C24—C25—H25	118.9
C2—Hg1—O1	83.6 (2)	C25—C26—C27	119.5 (8)
C1—Hg1—O1	82.9 (2)	C25—C26—H26	120.2
C1—N1—C3	109.3 (6)	C27—C26—H26	120.2
C1—N1—C5	127.0 (5)	C26—C27—C32	120.9 (9)
C3—N1—C5	122.9 (6)	C26—C27—C28	120.1 (8)
C1—N2—C4	108.4 (6)	C32—C27—C28	119.0 (9)
C1—N2—C16	126.4 (6)	C29—C28—C27	118.8 (8)
C4—N2—C16	125.2 (6)	C29—C28—C23	123.0 (7)
C2—N3—C20	108.8 (6)	C27—C28—C23	118.3 (7)
C2—N3—C19	126.1 (6)	C30—C29—C28	119.9 (9)
C20—N3—C19	125.1 (6)	C30—C29—H29	120.1
C2—N4—C21	110.4 (6)	C28—C29—H29	120.1
C2—N4—C22	124.6 (5)	C31—C30—C29	121.8 (10)
C21—N4—C22	125.1 (6)	C31—C30—H30	119.1
C18—O1—C17	118.5 (6)	C29—C30—H30	119.1
C18—O1—Hg1	120.0 (4)	C30—C31—C32	120.0 (9)
C17—O1—Hg1	121.5 (4)	C30—C31—H31	120.0
N1—C1—N2	106.9 (5)	C32—C31—H31	120.0
N1—C1—Hg1	131.0 (5)	C31—C32—C27	120.5 (9)
N2—C1—Hg1	121.6 (5)	C31—C32—H32	119.8
N4—C2—N3	106.6 (5)	C27—C32—H32	119.8
N4—C2—Hg1	132.4 (5)	F6—P1—F4	91.7 (4)
N3—C2—Hg1	119.9 (5)	F6—P1—F3	97.2 (5)
C4—C3—N1	106.8 (6)	F4—P1—F3	90.0 (3)
C4—C3—H3	126.6	F6—P1—F2	90.5 (3)
N1—C3—H3	126.6	F4—P1—F2	177.8 (4)
C3—C4—N2	108.6 (7)	F3—P1—F2	89.9 (3)
C3—C4—H4	125.7	F6—P1—F5	88.6 (5)
N2—C4—H4	125.7	F4—P1—F5	91.1 (3)
N1—C5—C6	115.4 (5)	F3—P1—F5	174.1 (4)
N1—C5—H5A	108.4	F2—P1—F5	88.8 (3)
C6—C5—H5A	108.4	F6—P1—F1	176.7 (5)
N1—C5—H5B	108.4	F4—P1—F1	88.3 (3)
C6—C5—H5B	108.4	F3—P1—F1	86.1 (4)
H5A—C5—H5B	107.5	F2—P1—F1	89.5 (3)
C7—C6—C11	119.9 (6)	F5—P1—F1	88.1 (4)
C7—C6—C5	119.0 (7)	F8'—P2—F12	84.9 (9)
C11—C6—C5	121.0 (6)	F8'—P2—F10	128.3 (8)
C6—C7—C8	121.1 (7)	F12—P2—F10	91.2 (4)
C6—C7—H7	119.5	F8'—P2—F7'	92.3 (6)
C8—C7—H7	119.5	F12—P2—F7'	127.2 (9)
C9—C8—C7	120.6 (7)	F10—P2—F7'	128.3 (10)
C9—C8—H8	119.7	F8'—P2—F11	140.5 (8)
C7—C8—H8	119.7	F12—P2—F11	91.5 (5)
C8—C9—C10	121.7 (7)	F10—P2—F11	91.0 (5)
C8—C9—H9	119.2	F7'—P2—F11	59.3 (9)
C10—C9—H9	119.2	F8'—P2—F11'	91.6 (6)
C9—C10—C15	122.4 (8)	F12—P2—F11'	36.5 (8)
C9—C10—C11	118.9 (7)	F10—P2—F11'	114.5 (8)
C15—C10—C11	118.7 (8)	F7'—P2—F11'	91.2 (6)
C12—C11—C6	122.9 (7)	F11—P2—F11'	64.6 (8)
C12—C11—C10	119.1 (7)	F8'—P2—F9	37.4 (8)
C6—C11—C10	117.8 (7)	F12—P2—F9	90.6 (5)
C13—C12—C11	119.4 (8)	F10—P2—F9	91.4 (4)
C13—C12—H12	120.3	F7'—P2—F9	117.5 (9)
C11—C12—H12	120.3	F11—P2—F9	176.7 (5)
C12—C13—C14	121.2 (9)	F11'—P2—F9	116.1 (8)
C12—C13—H13	119.4	F8'—P2—F9'	91.2 (6)
C14—C13—H13	119.4	F12—P2—F9'	142.0 (9)
C15—C14—C13	120.3 (9)	F10—P2—F9'	62.3 (9)
C15—C14—H14	119.8	F7'—P2—F9'	90.6 (6)
C13—C14—H14	119.8	F11—P2—F9'	114.1 (8)
C14—C15—C10	121.2 (9)	F11'—P2—F9'	176.7 (7)
C14—C15—H15	119.4	F9—P2—F9'	65.3 (8)
C10—C15—H15	119.4	F8'—P2—F7	94.1 (8)
N2—C16—C17	114.5 (6)	F12—P2—F7	178.6 (5)
N2—C16—H16A	108.6	F10—P2—F7	90.2 (4)
C17—C16—H16A	108.6	F7'—P2—F7	51.9 (10)
N2—C16—H16B	108.6	F11—P2—F7	88.7 (4)
C17—C16—H16B	108.6	F11'—P2—F7	142.7 (9)
H16A—C16—H16B	107.6	F9—P2—F7	89.1 (4)
O1—C17—C16	108.5 (6)	F9'—P2—F7	38.8 (9)
O1—C17—H17A	110.0	F8'—P2—F10'	177.4 (7)
C16—C17—H17A	110.0	F12—P2—F10'	93.8 (8)
O1—C17—H17B	110.0	F10—P2—F10'	49.4 (7)
C16—C17—H17B	110.0	F7'—P2—F10'	90.3 (5)
H17A—C17—H17B	108.4	F11—P2—F10'	41.7 (7)
O1—C18—C19	109.8 (7)	F11'—P2—F10'	88.7 (5)
O1—C18—H18A	109.7	F9—P2—F10'	140.6 (8)
C19—C18—H18A	109.7	F9'—P2—F10'	88.5 (5)
O1—C18—H18B	109.7	F7—P2—F10'	87.2 (7)
C19—C18—H18B	109.7	F8'—P2—F12'	89.8 (5)
H18A—C18—H18B	108.2	F12—P2—F12'	53.5 (8)
N3—C19—C18	113.1 (6)	F10—P2—F12'	49.7 (8)
N3—C19—H19A	109.0	F7'—P2—F12'	177.9 (7)
C18—C19—H19A	109.0	F11—P2—F12'	119.2 (8)
N3—C19—H19B	109.0	F11'—P2—F12'	89.3 (5)
C18—C19—H19B	109.0	F9—P2—F12'	64.1 (8)
H19A—C19—H19B	107.8	F9'—P2—F12'	88.8 (5)
C21—C20—N3	107.4 (6)	F7—P2—F12'	127.5 (9)
C21—C20—H20	126.3	F10'—P2—F12'	87.7 (5)
N3—C20—H20	126.3	F8'—P2—F8	51.9 (8)
C20—C21—N4	106.8 (6)	F12—P2—F8	90.6 (4)
C20—C21—H21	126.6	F10—P2—F8	178.2 (5)
N4—C21—H21	126.6	F7'—P2—F8	50.3 (10)
N4—C22—C23	115.2 (5)	F11—P2—F8	88.9 (4)
N4—C22—H22A	108.5	F11'—P2—F8	67.0 (8)
C23—C22—H22A	108.5	F9—P2—F8	88.6 (4)
N4—C22—H22B	108.5	F9'—P2—F8	116.2 (9)
C23—C22—H22B	108.5	F7—P2—F8	88.1 (4)
H22A—C22—H22B	107.5	F10'—P2—F8	130.4 (8)
C24—C23—C28	120.5 (7)	F12'—P2—F8	131.7 (9)
C24—C23—C22	121.6 (7)	N5—C33—C34	175.2 (15)
C28—C23—C22	117.8 (6)	C33—C34—H34A	109.5
C23—C24—C25	119.4 (8)	C33—C34—H34B	109.5
C23—C24—H24	120.3	H34A—C34—H34B	109.5
C25—C24—H24	120.3	C33—C34—H34C	109.5
C26—C25—C24	122.2 (8)	H34A—C34—H34C	109.5
C26—C25—H25	118.9	H34B—C34—H34C	109.5

C2—Hg1—O1—C18	28.4 (5)	C9—C10—C11—C6	1.7 (10)
C1—Hg1—O1—C18	−153.7 (5)	C15—C10—C11—C6	−176.9 (6)
C2—Hg1—O1—C17	−152.7 (5)	C6—C11—C12—C13	175.7 (7)
C1—Hg1—O1—C17	25.3 (5)	C10—C11—C12—C13	0.8 (11)
C3—N1—C1—N2	−0.3 (7)	C11—C12—C13—C14	−0.3 (14)
C5—N1—C1—N2	169.5 (6)	C12—C13—C14—C15	0.9 (15)
C3—N1—C1—Hg1	−172.4 (5)	C13—C14—C15—C10	−1.9 (15)
C5—N1—C1—Hg1	−2.5 (10)	C9—C10—C15—C14	−176.3 (8)
C4—N2—C1—N1	0.5 (7)	C11—C10—C15—C14	2.3 (13)
C16—N2—C1—N1	179.3 (6)	C1—N2—C16—C17	73.3 (9)
C4—N2—C1—Hg1	173.4 (5)	C4—N2—C16—C17	−108.0 (8)
C16—N2—C1—Hg1	−7.7 (9)	C18—O1—C17—C16	−166.3 (6)
C2—Hg1—C1—N1	151.3 (9)	Hg1—O1—C17—C16	14.7 (8)
O1—Hg1—C1—N1	142.7 (6)	N2—C16—C17—O1	−66.7 (8)
C2—Hg1—C1—N2	−19.8 (13)	C17—O1—C18—C19	−165.6 (6)
O1—Hg1—C1—N2	−28.3 (5)	Hg1—O1—C18—C19	13.4 (8)
C21—N4—C2—N3	−2.4 (8)	C2—N3—C19—C18	74.7 (10)
C22—N4—C2—N3	177.6 (6)	C20—N3—C19—C18	−104.0 (8)
C21—N4—C2—Hg1	−169.6 (5)	O1—C18—C19—N3	−67.1 (8)
C22—N4—C2—Hg1	10.3 (10)	C2—N3—C20—C21	−0.5 (9)
C20—N3—C2—N4	1.8 (8)	C19—N3—C20—C21	178.4 (7)
C19—N3—C2—N4	−177.1 (7)	N3—C20—C21—N4	−0.9 (9)
C20—N3—C2—Hg1	170.9 (5)	C2—N4—C21—C20	2.1 (9)
C19—N3—C2—Hg1	−8.0 (9)	C22—N4—C21—C20	−177.9 (7)
C1—Hg1—C2—N4	127.6 (10)	C2—N4—C22—C23	99.1 (7)
O1—Hg1—C2—N4	136.1 (7)	C21—N4—C22—C23	−81.0 (8)
C1—Hg1—C2—N3	−38.3 (13)	N4—C22—C23—C24	3.1 (9)
O1—Hg1—C2—N3	−29.7 (5)	N4—C22—C23—C28	−174.7 (5)
C1—N1—C3—C4	0.1 (8)	C28—C23—C24—C25	0.4 (10)
C5—N1—C3—C4	−170.3 (6)	C22—C23—C24—C25	−177.4 (6)
N1—C3—C4—N2	0.2 (9)	C23—C24—C25—C26	1.0 (12)
C1—N2—C4—C3	−0.4 (9)	C24—C25—C26—C27	−0.6 (13)
C16—N2—C4—C3	−179.3 (7)	C25—C26—C27—C32	176.6 (8)
C1—N1—C5—C6	33.7 (10)	C25—C26—C27—C28	−1.3 (12)
C3—N1—C5—C6	−157.7 (6)	C26—C27—C28—C29	−179.7 (7)
N1—C5—C6—C7	−103.0 (7)	C32—C27—C28—C29	2.3 (10)
N1—C5—C6—C11	80.6 (8)	C26—C27—C28—C23	2.6 (10)
C11—C6—C7—C8	0.1 (10)	C32—C27—C28—C23	−175.3 (7)
C5—C6—C7—C8	−176.2 (7)	C24—C23—C28—C29	−179.7 (7)
C6—C7—C8—C9	0.6 (12)	C22—C23—C28—C29	−1.9 (10)
C7—C8—C9—C10	−0.2 (12)	C24—C23—C28—C27	−2.2 (10)
C8—C9—C10—C15	177.6 (8)	C22—C23—C28—C27	175.7 (6)
C8—C9—C10—C11	−1.0 (11)	C27—C28—C29—C30	−2.9 (11)
C7—C6—C11—C12	−176.3 (7)	C23—C28—C29—C30	174.6 (7)
C5—C6—C11—C12	0.0 (10)	C28—C29—C30—C31	0.8 (13)
C7—C6—C11—C10	−1.3 (10)	C29—C30—C31—C32	2.0 (15)
C5—C6—C11—C10	175.0 (6)	C30—C31—C32—C27	−2.6 (14)
C9—C10—C11—C12	176.9 (7)	C26—C27—C32—C31	−177.6 (8)
C15—C10—C11—C12	−1.7 (10)	C28—C27—C32—C31	0.4 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···F3	0.97	2.50	3.384 (9)	151
C5—H5B···F7	0.97	2.39	3.307 (9)	157
C18—H18A···F4ⁱ	0.97	2.53	3.150 (10)	122
C22—H22B···F9ⁱⁱ	0.97	2.46	3.195 (11)	132
C24—H24···N4	0.93	2.50	2.847 (9)	103

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	[Hg(C₃₂H₃₀N4O)](PF₆)₂·C₂H₃N
M_r	1018.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.204 (2), 11.433 (3), 35.922 (10)
β (°)	92.837 (5)
V (Å³)	3775.7 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.26
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.448, 0.590
No. of measured, independent and observed [I > 2σ(I)] reflections	21427, 7729, 5450
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.101, 1.12
No. of reflections	7729
No. of parameters	552
No. of restraints	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −1.46

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···F3	0.97	2.50	3.384 (9)	151
C5—H5B···F7	0.97	2.39	3.307 (9)	157
C18—H18A···F4ⁱ	0.97	2.53	3.150 (10)	122
C22—H22B···F9ⁱⁱ	0.97	2.46	3.195 (11)	132
C24—H24···N4	0.93	2.50	2.847 (9)	103

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z.

Acknowledgements

The authors thank Shanxi Normal University for supporting this work.

References

Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363. CSD CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Wang, J.-W., Li, Q.-S., Xu, F.-B., Song, H.-B. & Zhang, Z.-Z. (2006). Eur. J. Org. Chem. pp. 1310–1316. Web of Science CSD CrossRef Google Scholar
Wang, J.-W., Song, H.-B., Li, Q.-S., Xu, F.-B. & Zhang, Z.-Z. (2005). Inorg. Chim. Acta, 358, 3653–3658. Web of Science CSD CrossRef CAS Google Scholar

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Volume 65| Part 2| February 2009| Page m217

doi:10.1107/S1600536809001743

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

[3,3′-Bis(1-naphthylmethyl)-1,1′-(2,2′-oxy­di­ethyl­ene)bis­­(imidazol-2-yl­­idene)]mercury(II) bis­­(hexa­fluorido­phosphate) aceto­nitrile solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[3,3′-Bis(1-naphthylmethyl)-1,1′-(2,2′-oxydiethylene)bis(imidazol-2-ylidene)]mercury(II) bis(hexafluoridophosphate) acetonitrile solvate