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Acta Cryst. (2007). E63, m1802    [ doi:10.1107/S1600536807026682 ]

{(R)-1,1'-Bis(1-naphthylmethyl)-3,3'-[1,1'-binaphthyl-2,2'-diyldi(oxyethylene)]di-1H-imidazol-2-yl}mercury(II) bis(hexafluoridophosphate) acetonitrile 3.5-solvate

J. Lin and G.-Y. Dong

Abstract top

In the title compound, [Hg(C52H42N4O2)](PF6)2·3.5CH3CN, the linear coordination geometry of the Hg ion [C-Hg-C = 174.4 (2)°] is formed by two C atoms from the imidazole fragments [Hg-C = 2.072 (6) and 2.090 (6) Å]. The crystal packing exhibits weak intermolecular C-H...F and C-H...N hydrogen bonds.

Comment top

In the title compound, (I), the cation is a 15-membered macrocyclic metal complex of carbene-naphthoxy ligand adopting a trans-conformation. The short distance of 3.657 (4) Å between the centroids of C5—C10 and N3—C39—N4—C40—C41 rings shows a presence of intramolecular π···π interaction. The linear coordination geometry of the Hg ion is formed by two C atoms from the imidazole fragments [Hg—C 2.072 (6), 2.090 (6) Å, C—Hg—C 174.4 (2)°].

The crystal packing is stabilized by the weak C—H···F and C—H···N interactions (Table 1).

Related literature top

The related rhodium and iridium complexes of the carbene–naphthoxy ligands were applied to the catalytic asymmetric hydrosilylation of acetophenone with diphenylsilane; see: Chianese & Crabtree (2005); Scheele et al. (2006).

Experimental top

The ligand (R)-2,2'-bis[imidazolium-3-oxyethyl-1-(1-menaphthyl)]-1,1'-binaphthyl bis(hexafluorophosphate) was prepared according to the reported procedure (Scheele et al., 2006). A stirred acetonitrile solution (25 ml) of the corresponding diazolium salt (104.7 mg, 0.10 mmol) and anhydrous Hg(OAc)2 (29.5 mg, 0.10 mmol) was heated at 353 K for 12 h, The remaining acetonitrile was then 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: 80%) Anal. Calcd. for C118H105F24Hg2N15O4: C, 51.01; H, 3.81; N, 7.56 Found: C, 50.99; H, 3.76; N 7.49.

Refinement top

All H-atoms were geometrically positioned [C—H 0.93–0.97 Å] and refined as riding with Uiso(H) =1.2–1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The cation structure of the title compound, shown with 30% probability displacement ellipsoids. Dashed lines indicate intramolecular hydrogen bonds and π-π stacking interactions.
{(R)-1,1'-Bis(1-naphthylmethyl)-3,3'-[1,1'-binaphthyl-2,2'- diyldi(oxyethylene)]di-1H-imidazol-2-yl}mercury(II) bis(hexafluoridophosphate) acetonitrile 3.5-solvate top
Crystal data top
[Hg(C52H42N4O2)](PF6)2·3.5C2H3NZ = 2
Mr = 1389.12F000 = 1386
Triclinic, P1Dx = 1.565 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 12.266 (4) ÅCell parameters from 923 reflections
b = 14.908 (6) Åθ = 2.8–22.6º
c = 16.946 (6) ŵ = 2.75 mm−1
α = 94.448 (6)ºT = 293 (2) K
β = 107.027 (6)ºBlock, white
γ = 92.066 (7)º0.20 × 0.14 × 0.12 mm
V = 2948.4 (19) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		11938 independent reflections
Radiation source: fine-focus sealed tube8762 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 293(2) Kθmax = 26.4º
phi and ω scansθmin = 1.3º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −15→11
Tmin = 0.634, Tmax = 0.782k = −18→16
17133 measured reflectionsl = −20→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.127  w = 1/[σ2(Fo2) + (0.0627P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
11938 reflectionsΔρmax = 0.97 e Å−3
770 parametersΔρmin = −0.78 e Å−3
21 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Hg(C52H42N4O2)](PF6)2·3.5C2H3Nγ = 92.066 (7)º
Mr = 1389.12V = 2948.4 (19) Å3
Triclinic, P1Z = 2
a = 12.266 (4) ÅMo Kα
b = 14.908 (6) ŵ = 2.75 mm−1
c = 16.946 (6) ÅT = 293 (2) K
α = 94.448 (6)º0.20 × 0.14 × 0.12 mm
β = 107.027 (6)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		11938 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		8762 reflections with I > 2σ(I)
Tmin = 0.634, Tmax = 0.782Rint = 0.031
17133 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04721 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.04Δρmax = 0.97 e Å−3
11938 reflectionsΔρmin = −0.78 e Å−3
770 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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
Hg10.84498 (2)0.923454 (18)0.734041 (15)0.03985 (9)
N10.8148 (4)1.0221 (3)0.8924 (3)0.0415 (12)
N20.9675 (4)1.0740 (4)0.8693 (3)0.0410 (12)
N30.9075 (4)0.7732 (3)0.6265 (3)0.0403 (12)
N40.7265 (4)0.7915 (4)0.5801 (3)0.0436 (13)
O10.7722 (4)0.8275 (3)0.9203 (3)0.0497 (11)
O20.9873 (4)0.7644 (3)0.8017 (3)0.0461 (11)
C10.7833 (5)0.7046 (4)0.8293 (4)0.0392 (14)
C20.7187 (5)0.7712 (4)0.8499 (4)0.0407 (14)
C30.6032 (5)0.7774 (4)0.8034 (4)0.0465 (16)
H30.55970.82060.82010.056*
C40.5561 (5)0.7204 (5)0.7344 (4)0.0488 (16)
H40.47990.72440.70450.059*
C50.6209 (6)0.6547 (5)0.7070 (4)0.0462 (16)
C60.7356 (5)0.6464 (4)0.7555 (4)0.0400 (14)
C70.7973 (6)0.5790 (5)0.7277 (4)0.0530 (18)
H70.87140.57040.75930.064*
C80.7508 (7)0.5266 (5)0.6559 (5)0.067 (2)
H80.79410.48370.63860.081*
C90.6381 (7)0.5359 (6)0.6071 (5)0.069 (2)
H90.60760.49940.55790.082*
C100.5735 (6)0.5983 (5)0.6320 (5)0.0598 (19)
H100.49870.60400.60000.072*
C110.8988 (5)0.6914 (4)0.8872 (4)0.0402 (14)
C120.9974 (5)0.7190 (4)0.8714 (4)0.0406 (15)
C131.1056 (6)0.7054 (5)0.9259 (4)0.0514 (17)
H131.17160.72560.91460.062*
C141.1131 (6)0.6621 (5)0.9955 (4)0.058 (2)
H141.18460.65181.03050.070*
C151.0162 (7)0.6335 (5)1.0147 (4)0.0514 (18)
C160.9066 (6)0.6474 (5)0.9608 (4)0.0482 (16)
C170.8098 (7)0.6182 (5)0.9819 (5)0.065 (2)
H170.73740.62750.94750.078*
C180.8203 (10)0.5758 (6)1.0528 (6)0.084 (3)
H180.75540.55621.06590.101*
C190.9286 (10)0.5622 (6)1.1051 (5)0.082 (3)
H190.93540.53371.15300.099*
C201.0235 (8)0.5898 (5)1.0869 (5)0.070 (2)
H201.09480.57981.12250.084*
C210.7127 (6)0.9027 (4)0.9414 (4)0.0458 (16)
H21A0.75200.92730.99770.055*
H21B0.63630.88150.93970.055*
C220.7044 (5)0.9756 (4)0.8850 (4)0.0467 (16)
H22A0.67110.94980.82830.056*
H22B0.65341.01930.89700.056*
C230.8763 (5)1.0159 (4)0.8385 (4)0.0414 (15)
C240.8692 (6)1.0845 (5)0.9582 (4)0.0553 (18)
H240.84551.10041.00450.066*
C250.9630 (6)1.1177 (5)0.9423 (4)0.0522 (18)
H251.01541.16230.97490.063*
C261.0481 (5)1.1031 (5)0.8264 (4)0.0463 (16)
H26A1.05601.05370.78810.056*
H26B1.12231.11770.86670.056*
C271.0118 (5)1.1836 (4)0.7794 (4)0.0431 (15)
C280.9035 (6)1.2123 (5)0.7634 (5)0.061 (2)
H280.85091.18280.78400.074*
C290.8702 (7)1.2868 (6)0.7158 (6)0.073 (2)
H290.79581.30480.70490.088*
C300.9450 (9)1.3312 (6)0.6865 (5)0.075 (2)
H300.92221.37970.65560.089*
C311.0576 (7)1.3048 (5)0.7023 (4)0.0586 (19)
C321.0923 (6)1.2297 (5)0.7483 (4)0.0490 (17)
C331.2042 (6)1.2028 (6)0.7597 (5)0.062 (2)
H331.22871.15320.78870.075*
C341.2777 (8)1.2503 (7)0.7277 (6)0.081 (3)
H341.35131.23200.73480.097*
C351.2428 (10)1.3252 (7)0.6852 (6)0.086 (3)
H351.29391.35700.66490.103*
C361.1366 (9)1.3521 (6)0.6729 (5)0.073 (2)
H361.11501.40270.64460.088*
C371.0546 (5)0.7325 (5)0.7499 (4)0.0491 (17)
H37A1.03600.66880.73260.059*
H37B1.13530.74070.78000.059*
C381.0277 (5)0.7857 (5)0.6761 (4)0.0460 (16)
H38A1.04620.84910.69460.055*
H38B1.07530.76770.64160.055*
C390.8233 (5)0.8233 (4)0.6380 (3)0.0370 (14)
C400.8621 (6)0.7083 (5)0.5621 (4)0.0545 (18)
H400.90230.66470.54230.065*
C410.7516 (6)0.7183 (5)0.5329 (4)0.0536 (18)
H410.70000.68320.48920.064*
C420.6119 (5)0.8276 (4)0.5654 (4)0.0447 (15)
H42A0.57310.80070.60080.054*
H42B0.56720.81100.50830.054*
C430.6187 (5)0.9279 (5)0.5823 (4)0.0463 (16)
C440.5870 (6)0.9657 (6)0.6479 (4)0.059 (2)
H440.56160.92840.68120.070*
C450.5921 (7)1.0592 (7)0.6659 (6)0.077 (3)
H450.56951.08350.71050.093*
C460.6290 (7)1.1130 (6)0.6194 (7)0.079 (3)
H460.63451.17490.63340.095*
C470.6606 (6)1.0797 (6)0.5489 (6)0.067 (2)
C480.6555 (5)0.9848 (5)0.5302 (4)0.0503 (17)
C490.6852 (6)0.9507 (6)0.4588 (5)0.061 (2)
H490.68340.88870.44610.073*
C500.7165 (7)1.0083 (8)0.4086 (6)0.084 (3)
H500.73660.98510.36260.100*
C510.7181 (9)1.1014 (9)0.4262 (8)0.100 (4)
H510.73591.13970.39030.120*
C520.6943 (8)1.1366 (7)0.4947 (8)0.090 (3)
H520.69991.19880.50680.108*
P10.19960 (17)0.60006 (14)0.56869 (14)0.0595 (5)
P20.32712 (17)0.93227 (15)0.85090 (13)0.0612 (5)
F10.2784 (5)0.6251 (4)0.5131 (4)0.0935 (16)
F20.1375 (6)0.5222 (4)0.5022 (4)0.135 (3)
F30.1110 (4)0.6682 (4)0.5241 (3)0.0961 (17)
F40.2606 (5)0.6805 (4)0.6356 (3)0.0995 (17)
F50.2898 (5)0.5351 (4)0.6149 (5)0.129 (2)
F60.1198 (5)0.5779 (4)0.6244 (3)0.0908 (16)
F70.2254 (8)0.9111 (6)0.8835 (6)0.183 (4)
F80.4160 (12)0.9258 (8)0.9327 (7)0.275 (7)
F90.3290 (7)0.8325 (5)0.8279 (9)0.225 (6)
F100.2386 (6)0.9440 (7)0.7697 (4)0.165 (3)
F110.3235 (6)1.0328 (4)0.8804 (5)0.132 (2)
F120.4274 (6)0.9544 (6)0.8179 (7)0.185 (4)
N50.4918 (10)0.6825 (9)0.3671 (10)0.156 (5)
C530.4547 (12)0.6419 (10)0.3053 (12)0.129 (5)
C540.4075 (15)0.5882 (11)0.2256 (10)0.182 (7)
H54A0.46820.56060.20950.273*
H54B0.36970.62660.18430.273*
H54C0.35370.54220.23060.273*
N6−0.0360 (7)0.0136 (5)0.6310 (4)0.076 (2)
C55−0.0159 (7)0.0671 (6)0.5928 (5)0.0584 (19)
C560.0109 (8)0.1352 (5)0.5444 (5)0.071 (2)
H56A0.08220.16690.57470.106*
H56B−0.04850.17680.53340.106*
H56C0.01690.10720.49300.106*
N70.3716 (18)0.7959 (13)0.1389 (12)0.183 (7)
C570.4303 (18)0.7870 (14)0.1027 (12)0.137 (7)
C580.5033 (18)0.7666 (15)0.0536 (12)0.211 (10)
H58A0.57390.74700.08790.316*
H58B0.51840.81940.02860.316*
H58C0.46710.71950.01100.316*
N80.3182 (17)0.5906 (14)0.8172 (12)0.116 (6)0.50
C590.3992 (19)0.5805 (17)0.8650 (15)0.127 (9)0.50
C600.501 (2)0.539 (2)0.9171 (19)0.198 (15)0.50
H60A0.50610.55070.97450.297*0.50
H60B0.56900.56360.90750.297*0.50
H60C0.49420.47470.90270.297*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.03965 (14)0.04213 (15)0.03645 (13)0.00516 (9)0.01044 (9)−0.00233 (9)
N10.047 (3)0.038 (3)0.040 (3)0.003 (2)0.016 (2)−0.004 (2)
N20.040 (3)0.043 (3)0.041 (3)0.003 (2)0.013 (2)0.003 (2)
N30.045 (3)0.043 (3)0.036 (3)0.008 (2)0.015 (2)0.000 (2)
N40.043 (3)0.044 (3)0.042 (3)0.001 (2)0.011 (2)0.004 (2)
O10.048 (3)0.044 (3)0.052 (3)0.009 (2)0.010 (2)−0.008 (2)
O20.038 (2)0.057 (3)0.047 (2)0.013 (2)0.016 (2)0.008 (2)
C10.039 (3)0.036 (3)0.043 (3)0.003 (3)0.012 (3)0.006 (3)
C20.042 (4)0.037 (4)0.043 (3)−0.002 (3)0.014 (3)0.000 (3)
C30.037 (4)0.043 (4)0.062 (4)0.003 (3)0.019 (3)0.001 (3)
C40.031 (3)0.051 (4)0.060 (4)−0.002 (3)0.010 (3)0.002 (3)
C50.043 (4)0.046 (4)0.047 (4)−0.004 (3)0.011 (3)0.003 (3)
C60.041 (4)0.036 (4)0.043 (3)0.000 (3)0.013 (3)0.003 (3)
C70.047 (4)0.052 (4)0.056 (4)0.013 (3)0.011 (3)−0.007 (3)
C80.067 (5)0.060 (5)0.068 (5)0.021 (4)0.012 (4)−0.012 (4)
C90.074 (6)0.061 (5)0.060 (5)0.006 (4)0.006 (4)−0.012 (4)
C100.053 (4)0.059 (5)0.057 (4)0.002 (4)0.004 (3)−0.006 (4)
C110.040 (4)0.037 (4)0.041 (3)0.007 (3)0.008 (3)0.000 (3)
C120.039 (4)0.041 (4)0.036 (3)0.010 (3)0.004 (3)−0.002 (3)
C130.039 (4)0.056 (4)0.053 (4)0.003 (3)0.006 (3)−0.004 (3)
C140.056 (5)0.053 (5)0.047 (4)0.013 (4)−0.013 (3)0.007 (3)
C150.071 (5)0.037 (4)0.038 (3)0.011 (3)0.005 (3)−0.002 (3)
C160.055 (4)0.042 (4)0.044 (4)0.006 (3)0.012 (3)−0.001 (3)
C170.066 (5)0.063 (5)0.069 (5)0.009 (4)0.023 (4)0.019 (4)
C180.118 (8)0.069 (6)0.082 (6)0.007 (5)0.050 (6)0.024 (5)
C190.129 (9)0.062 (6)0.053 (5)0.014 (6)0.017 (5)0.024 (4)
C200.092 (7)0.052 (5)0.054 (5)0.008 (4)0.002 (4)0.011 (4)
C210.052 (4)0.045 (4)0.045 (4)0.001 (3)0.024 (3)−0.003 (3)
C220.044 (4)0.045 (4)0.055 (4)0.003 (3)0.021 (3)0.000 (3)
C230.042 (4)0.039 (4)0.042 (3)0.006 (3)0.010 (3)0.001 (3)
C240.065 (5)0.054 (4)0.046 (4)−0.003 (4)0.019 (3)−0.014 (3)
C250.056 (4)0.045 (4)0.049 (4)−0.002 (3)0.010 (3)−0.010 (3)
C260.039 (4)0.051 (4)0.048 (4)0.001 (3)0.013 (3)0.007 (3)
C270.042 (4)0.038 (4)0.042 (3)0.001 (3)0.003 (3)−0.004 (3)
C280.052 (4)0.054 (5)0.078 (5)0.012 (3)0.016 (4)0.011 (4)
C290.060 (5)0.063 (6)0.087 (6)0.025 (4)0.006 (5)0.010 (5)
C300.097 (7)0.058 (5)0.065 (5)0.024 (5)0.014 (5)0.015 (4)
C310.083 (6)0.049 (4)0.043 (4)0.004 (4)0.018 (4)0.005 (3)
C320.052 (4)0.047 (4)0.042 (4)0.004 (3)0.005 (3)0.000 (3)
C330.058 (5)0.071 (5)0.060 (5)−0.002 (4)0.020 (4)0.013 (4)
C340.065 (6)0.093 (7)0.091 (6)−0.004 (5)0.028 (5)0.027 (6)
C350.108 (8)0.081 (7)0.075 (6)−0.031 (6)0.041 (6)0.010 (5)
C360.099 (7)0.059 (5)0.063 (5)−0.004 (5)0.022 (5)0.014 (4)
C370.037 (4)0.062 (5)0.049 (4)0.009 (3)0.016 (3)−0.004 (3)
C380.038 (4)0.053 (4)0.052 (4)0.008 (3)0.021 (3)0.002 (3)
C390.039 (3)0.039 (4)0.034 (3)0.000 (3)0.012 (3)0.004 (3)
C400.062 (5)0.053 (4)0.050 (4)0.008 (4)0.021 (4)−0.006 (3)
C410.066 (5)0.047 (4)0.042 (4)−0.002 (3)0.012 (3)−0.011 (3)
C420.036 (3)0.049 (4)0.046 (4)0.003 (3)0.006 (3)0.012 (3)
C430.035 (3)0.050 (4)0.044 (4)0.005 (3)−0.002 (3)0.002 (3)
C440.052 (4)0.073 (6)0.046 (4)0.018 (4)0.005 (3)0.008 (4)
C450.062 (5)0.090 (7)0.068 (6)0.021 (5)0.004 (4)−0.018 (5)
C460.056 (5)0.053 (5)0.104 (7)0.016 (4)−0.010 (5)−0.018 (5)
C470.038 (4)0.056 (5)0.091 (6)0.001 (3)−0.010 (4)0.012 (5)
C480.031 (3)0.053 (4)0.057 (4)−0.001 (3)−0.003 (3)0.012 (3)
C490.049 (4)0.073 (5)0.060 (5)0.006 (4)0.009 (4)0.022 (4)
C500.066 (6)0.102 (8)0.089 (7)0.010 (5)0.027 (5)0.035 (6)
C510.073 (7)0.100 (9)0.128 (10)−0.010 (6)0.023 (7)0.052 (8)
C520.054 (5)0.061 (6)0.137 (10)−0.006 (4)−0.007 (6)0.034 (6)
P10.0561 (12)0.0521 (12)0.0762 (13)0.0048 (9)0.0300 (10)0.0009 (10)
P20.0511 (12)0.0636 (14)0.0654 (12)0.0107 (10)0.0131 (10)−0.0023 (10)
F10.094 (4)0.086 (4)0.126 (4)0.011 (3)0.070 (3)0.016 (3)
F20.135 (5)0.115 (5)0.160 (6)−0.048 (4)0.080 (5)−0.074 (5)
F30.081 (4)0.128 (5)0.087 (3)0.045 (3)0.029 (3)0.023 (3)
F40.103 (4)0.087 (4)0.092 (4)−0.021 (3)0.013 (3)−0.014 (3)
F50.114 (5)0.111 (5)0.196 (7)0.061 (4)0.076 (5)0.082 (5)
F60.103 (4)0.087 (4)0.107 (4)0.001 (3)0.069 (3)0.008 (3)
F70.224 (9)0.172 (8)0.223 (9)−0.023 (6)0.179 (8)0.016 (7)
F80.303 (14)0.206 (11)0.186 (10)0.014 (10)−0.140 (10)0.059 (8)
F90.128 (6)0.073 (5)0.454 (17)−0.001 (4)0.080 (8)−0.077 (7)
F100.130 (6)0.259 (11)0.078 (4)−0.013 (6)−0.009 (4)0.013 (5)
F110.114 (5)0.092 (5)0.180 (7)0.020 (4)0.037 (5)−0.027 (5)
F120.088 (5)0.175 (8)0.314 (12)−0.024 (5)0.116 (7)−0.058 (8)
N50.100 (8)0.114 (10)0.226 (16)0.006 (7)0.017 (9)−0.032 (10)
C530.093 (10)0.097 (11)0.197 (17)−0.009 (7)0.049 (11)−0.004 (10)
C540.212 (18)0.165 (16)0.160 (15)−0.069 (13)0.060 (13)−0.012 (13)
N60.097 (6)0.062 (5)0.068 (4)−0.013 (4)0.025 (4)0.008 (4)
C550.060 (5)0.059 (5)0.052 (4)−0.004 (4)0.016 (4)−0.007 (4)
C560.095 (6)0.058 (5)0.064 (5)−0.004 (4)0.029 (5)0.014 (4)
N70.20 (2)0.141 (13)0.184 (17)0.008 (13)0.030 (13)−0.007 (12)
C570.149 (19)0.131 (15)0.113 (14)−0.009 (13)0.008 (11)0.038 (12)
C580.21 (2)0.26 (3)0.147 (16)−0.010 (18)0.014 (15)0.083 (17)
N80.114 (9)0.120 (10)0.112 (9)0.023 (8)0.023 (8)0.022 (8)
C590.127 (12)0.134 (12)0.128 (12)−0.015 (9)0.050 (9)0.013 (9)
C600.201 (17)0.205 (18)0.195 (17)−0.002 (10)0.071 (10)0.025 (10)
Geometric parameters (Å, °) top
Hg1—C392.072 (6)C31—C361.405 (12)
Hg1—C232.090 (6)C31—C321.420 (10)
N1—C231.345 (8)C32—C331.407 (10)
N1—C241.383 (8)C33—C341.381 (11)
N1—C221.466 (8)C33—H330.9300
N2—C231.338 (8)C34—C351.388 (13)
N2—C251.369 (8)C34—H340.9300
N2—C261.461 (8)C35—C361.339 (13)
N3—C391.346 (8)C35—H350.9300
N3—C401.372 (8)C36—H360.9300
N3—C381.465 (8)C37—C381.494 (9)
N4—C391.342 (7)C37—H37A0.9700
N4—C411.400 (8)C37—H37B0.9700
N4—C421.482 (8)C38—H38A0.9700
O1—C21.380 (7)C38—H38B0.9700
O1—C211.437 (7)C40—C411.318 (10)
O2—C121.382 (7)C40—H400.9300
O2—C371.437 (7)C41—H410.9300
C1—C21.379 (9)C42—C431.494 (9)
C1—C61.423 (8)C42—H42A0.9700
C1—C111.498 (8)C42—H42B0.9700
C2—C31.416 (9)C43—C441.369 (10)
C3—C41.355 (9)C43—C481.424 (10)
C3—H30.9300C44—C451.399 (12)
C4—C51.417 (9)C44—H440.9300
C4—H40.9300C45—C461.323 (13)
C5—C61.421 (9)C45—H450.9300
C5—C101.424 (9)C46—C471.421 (13)
C6—C71.413 (9)C46—H460.9300
C7—C81.352 (10)C47—C481.420 (10)
C7—H70.9300C47—C521.433 (14)
C8—C91.405 (10)C48—C491.425 (10)
C8—H80.9300C49—C501.375 (12)
C9—C101.363 (10)C49—H490.9300
C9—H90.9300C50—C511.396 (15)
C10—H100.9300C50—H500.9300
C11—C121.369 (9)C51—C521.350 (15)
C11—C161.433 (9)C51—H510.9300
C12—C131.410 (9)C52—H520.9300
C13—C141.369 (10)P1—F21.558 (6)
C13—H130.9300P1—F51.570 (6)
C14—C151.383 (11)P1—F31.582 (5)
C14—H140.9300P1—F41.584 (5)
C15—C201.413 (10)P1—F11.589 (5)
C15—C161.419 (9)P1—F61.589 (5)
C16—C171.402 (10)P2—F81.504 (8)
C17—C181.376 (11)P2—F101.510 (7)
C17—H170.9300P2—F91.510 (7)
C18—C191.396 (13)P2—F121.529 (7)
C18—H180.9300P2—F71.538 (7)
C19—C201.345 (13)P2—F111.549 (6)
C19—H190.9300N5—C531.127 (18)
C20—H200.9300C53—C541.46 (2)
C21—C221.489 (9)C54—H54A0.9600
C21—H21A0.9700C54—H54B0.9600
C21—H21B0.9700C54—H54C0.9600
C22—H22A0.9700N6—C551.129 (10)
C22—H22B0.9700C55—C561.439 (11)
C24—C251.342 (10)C56—H56A0.9600
C24—H240.9300C56—H56B0.9600
C25—H250.9300C56—H56C0.9600
C26—C271.501 (9)N7—C571.08 (2)
C26—H26A0.9700C57—C581.42 (2)
C26—H26B0.9700C58—H58A0.9600
C27—C281.367 (9)C58—H58B0.9600
C27—C321.427 (10)C58—H58C0.9600
C28—C291.425 (11)N8—C591.107 (9)
C28—H280.9300C59—C601.493 (9)
C29—C301.342 (12)C60—H60A0.9600
C29—H290.9300C60—H60B0.9600
C30—C311.404 (12)C60—H60C0.9600
C30—H300.9300
C39—Hg1—C23174.4 (2)C33—C34—H34119.6
C23—N1—C24109.4 (5)C35—C34—H34119.6
C23—N1—C22128.0 (5)C36—C35—C34120.8 (9)
C24—N1—C22122.6 (5)C36—C35—H35119.6
C23—N2—C25109.7 (6)C34—C35—H35119.6
C23—N2—C26126.8 (5)C35—C36—C31120.7 (9)
C25—N2—C26122.3 (6)C35—C36—H36119.7
C39—N3—C40109.0 (5)C31—C36—H36119.7
C39—N3—C38125.2 (5)O2—C37—C38107.5 (5)
C40—N3—C38125.8 (5)O2—C37—H37A110.2
C39—N4—C41108.4 (6)C38—C37—H37A110.2
C39—N4—C42127.0 (5)O2—C37—H37B110.2
C41—N4—C42124.6 (5)C38—C37—H37B110.2
C2—O1—C21118.4 (5)H37A—C37—H37B108.5
C12—O2—C37115.3 (5)N3—C38—C37112.7 (5)
C2—C1—C6118.9 (6)N3—C38—H38A109.1
C2—C1—C11119.5 (5)C37—C38—H38A109.1
C6—C1—C11121.4 (5)N3—C38—H38B109.1
C1—C2—O1115.8 (5)C37—C38—H38B109.1
C1—C2—C3121.2 (6)H38A—C38—H38B107.8
O1—C2—C3122.9 (6)N4—C39—N3107.1 (5)
C4—C3—C2120.0 (6)N4—C39—Hg1128.6 (5)
C4—C3—H3120.0N3—C39—Hg1124.1 (4)
C2—C3—H3120.0C41—C40—N3108.3 (6)
C3—C4—C5121.1 (6)C41—C40—H40125.8
C3—C4—H4119.4N3—C40—H40125.8
C5—C4—H4119.4C40—C41—N4107.2 (6)
C4—C5—C6118.8 (6)C40—C41—H41126.4
C4—C5—C10121.2 (6)N4—C41—H41126.4
C6—C5—C10120.0 (6)N4—C42—C43112.0 (5)
C7—C6—C5117.5 (6)N4—C42—H42A109.2
C7—C6—C1122.8 (6)C43—C42—H42A109.2
C5—C6—C1119.7 (6)N4—C42—H42B109.2
C8—C7—C6121.4 (6)C43—C42—H42B109.2
C8—C7—H7119.3H42A—C42—H42B107.9
C6—C7—H7119.3C44—C43—C48119.4 (7)
C7—C8—C9121.1 (7)C44—C43—C42119.7 (7)
C7—C8—H8119.4C48—C43—C42120.9 (6)
C9—C8—H8119.4C43—C44—C45121.6 (8)
C10—C9—C8120.1 (7)C43—C44—H44119.2
C10—C9—H9120.0C45—C44—H44119.2
C8—C9—H9120.0C46—C45—C44119.8 (9)
C9—C10—C5119.9 (7)C46—C45—H45120.1
C9—C10—H10120.1C44—C45—H45120.1
C5—C10—H10120.1C45—C46—C47122.4 (9)
C12—C11—C16118.9 (6)C45—C46—H46118.8
C12—C11—C1122.0 (6)C47—C46—H46118.8
C16—C11—C1119.2 (6)C48—C47—C46118.0 (8)
C11—C12—O2117.7 (5)C48—C47—C52118.5 (9)
C11—C12—C13121.5 (6)C46—C47—C52123.5 (9)
O2—C12—C13120.8 (6)C47—C48—C43118.8 (7)
C14—C13—C12119.6 (7)C47—C48—C49118.5 (7)
C14—C13—H13120.2C43—C48—C49122.7 (7)
C12—C13—H13120.2C50—C49—C48120.7 (9)
C13—C14—C15121.2 (6)C50—C49—H49119.6
C13—C14—H14119.4C48—C49—H49119.6
C15—C14—H14119.4C49—C50—C51120.4 (10)
C14—C15—C20121.4 (7)C49—C50—H50119.8
C14—C15—C16119.8 (6)C51—C50—H50119.8
C20—C15—C16118.9 (8)C52—C51—C50120.8 (10)
C17—C16—C15118.6 (7)C52—C51—H51119.6
C17—C16—C11122.4 (6)C50—C51—H51119.6
C15—C16—C11119.1 (6)C51—C52—C47121.1 (10)
C18—C17—C16120.9 (8)C51—C52—H52119.5
C18—C17—H17119.5C47—C52—H52119.5
C16—C17—H17119.5F2—P1—F591.3 (4)
C17—C18—C19119.8 (9)F2—P1—F390.5 (4)
C17—C18—H18120.1F5—P1—F3178.1 (4)
C19—C18—H18120.1F2—P1—F4178.8 (4)
C20—C19—C18120.9 (8)F5—P1—F489.9 (4)
C20—C19—H19119.5F3—P1—F488.3 (3)
C18—C19—H19119.5F2—P1—F190.0 (3)
C19—C20—C15120.9 (8)F5—P1—F190.5 (3)
C19—C20—H20119.5F3—P1—F189.3 (3)
C15—C20—H20119.5F4—P1—F190.2 (3)
O1—C21—C22113.2 (5)F2—P1—F690.9 (3)
O1—C21—H21A108.9F5—P1—F690.8 (3)
C22—C21—H21A108.9F3—P1—F689.4 (3)
O1—C21—H21B108.9F4—P1—F688.8 (3)
C22—C21—H21B108.9F1—P1—F6178.4 (3)
H21A—C21—H21B107.8F8—P2—F10177.0 (6)
N1—C22—C21113.5 (6)F8—P2—F991.0 (7)
N1—C22—H22A108.9F10—P2—F991.9 (6)
C21—C22—H22A108.9F8—P2—F1285.9 (7)
N1—C22—H22B108.9F10—P2—F1293.5 (5)
C21—C22—H22B108.9F9—P2—F1292.3 (5)
H22A—C22—H22B107.7F8—P2—F794.6 (8)
N2—C23—N1106.7 (5)F10—P2—F785.9 (5)
N2—C23—Hg1126.6 (5)F9—P2—F788.3 (5)
N1—C23—Hg1126.4 (5)F12—P2—F7179.2 (6)
C25—C24—N1106.6 (6)F8—P2—F1186.5 (6)
C25—C24—H24126.7F10—P2—F1190.6 (5)
N1—C24—H24126.7F9—P2—F11175.8 (6)
C24—C25—N2107.6 (6)F12—P2—F1190.9 (4)
C24—C25—H25126.2F7—P2—F1188.5 (4)
N2—C25—H25126.2N5—C53—C54179 (2)
N2—C26—C27113.0 (5)C53—C54—H54A109.5
N2—C26—H26A109.0C53—C54—H54B109.5
C27—C26—H26A109.0H54A—C54—H54B109.5
N2—C26—H26B109.0C53—C54—H54C109.5
C27—C26—H26B109.0H54A—C54—H54C109.5
H26A—C26—H26B107.8H54B—C54—H54C109.5
C28—C27—C32119.3 (7)N6—C55—C56179.5 (10)
C28—C27—C26122.1 (6)C55—C56—H56A109.5
C32—C27—C26118.6 (6)C55—C56—H56B109.5
C27—C28—C29120.8 (8)H56A—C56—H56B109.5
C27—C28—H28119.6C55—C56—H56C109.5
C29—C28—H28119.6H56A—C56—H56C109.5
C30—C29—C28120.6 (8)H56B—C56—H56C109.5
C30—C29—H29119.7N7—C57—C58174 (3)
C28—C29—H29119.7C57—C58—H58A109.5
C29—C30—C31120.4 (8)C57—C58—H58B109.5
C29—C30—H30119.8H58A—C58—H58B109.5
C31—C30—H30119.8C57—C58—H58C109.5
C30—C31—C36120.5 (8)H58A—C58—H58C109.5
C30—C31—C32120.0 (7)H58B—C58—H58C109.5
C36—C31—C32119.5 (8)N8—C59—C60163 (3)
C33—C32—C31118.3 (7)C59—C60—H60A109.5
C33—C32—C27122.8 (7)C59—C60—H60B109.5
C31—C32—C27118.8 (7)H60A—C60—H60B109.5
C34—C33—C32119.8 (8)C59—C60—H60C109.5
C34—C33—H33120.1H60A—C60—H60C109.5
C32—C33—H33120.1H60B—C60—H60C109.5
C33—C34—C35120.7 (9)
C6—C1—C2—O1−177.3 (5)N1—C24—C25—N2−2.0 (8)
C11—C1—C2—O16.3 (9)C23—N2—C25—C241.7 (8)
C6—C1—C2—C35.8 (9)C26—N2—C25—C24169.9 (6)
C11—C1—C2—C3−170.6 (6)C23—N2—C26—C2788.2 (8)
C21—O1—C2—C1175.1 (6)C25—N2—C26—C27−77.9 (7)
C21—O1—C2—C3−8.0 (9)N2—C26—C27—C28−14.1 (9)
C1—C2—C3—C4−3.8 (10)N2—C26—C27—C32167.9 (5)
O1—C2—C3—C4179.5 (6)C32—C27—C28—C290.6 (11)
C2—C3—C4—C5−0.8 (10)C26—C27—C28—C29−177.5 (7)
C3—C4—C5—C63.0 (10)C27—C28—C29—C30−1.0 (13)
C3—C4—C5—C10−176.3 (7)C28—C29—C30—C310.1 (13)
C4—C5—C6—C7178.6 (6)C29—C30—C31—C36−179.0 (8)
C10—C5—C6—C7−2.1 (10)C29—C30—C31—C321.1 (12)
C4—C5—C6—C1−0.9 (9)C30—C31—C32—C33177.2 (7)
C10—C5—C6—C1178.4 (6)C36—C31—C32—C33−2.7 (10)
C2—C1—C6—C7177.1 (7)C30—C31—C32—C27−1.5 (10)
C11—C1—C6—C7−6.5 (10)C36—C31—C32—C27178.6 (7)
C2—C1—C6—C5−3.4 (9)C28—C27—C32—C33−178.0 (7)
C11—C1—C6—C5172.9 (6)C26—C27—C32—C330.2 (10)
C5—C6—C7—C82.6 (11)C28—C27—C32—C310.6 (10)
C1—C6—C7—C8−177.9 (7)C26—C27—C32—C31178.8 (6)
C6—C7—C8—C9−1.5 (13)C31—C32—C33—C341.2 (11)
C7—C8—C9—C10−0.2 (14)C27—C32—C33—C34179.8 (7)
C8—C9—C10—C50.7 (13)C32—C33—C34—C350.8 (13)
C4—C5—C10—C9179.8 (8)C33—C34—C35—C36−1.2 (15)
C6—C5—C10—C90.5 (11)C34—C35—C36—C31−0.4 (14)
C2—C1—C11—C12−104.9 (7)C30—C31—C36—C35−177.5 (8)
C6—C1—C11—C1278.8 (8)C32—C31—C36—C352.4 (12)
C2—C1—C11—C1676.1 (8)C12—O2—C37—C38176.9 (5)
C6—C1—C11—C16−100.2 (7)C39—N3—C38—C3789.3 (7)
C16—C11—C12—O2−177.6 (5)C40—N3—C38—C37−89.5 (7)
C1—C11—C12—O23.4 (9)O2—C37—C38—N3−61.9 (7)
C16—C11—C12—C13−0.2 (9)C41—N4—C39—N31.6 (7)
C1—C11—C12—C13−179.3 (6)C42—N4—C39—N3−177.0 (6)
C37—O2—C12—C11−131.8 (6)C41—N4—C39—Hg1−174.4 (5)
C37—O2—C12—C1350.9 (8)C42—N4—C39—Hg17.0 (9)
C11—C12—C13—C141.2 (10)C40—N3—C39—N4−1.5 (7)
O2—C12—C13—C14178.4 (6)C38—N3—C39—N4179.5 (5)
C12—C13—C14—C15−1.7 (11)C40—N3—C39—Hg1174.7 (5)
C13—C14—C15—C20−179.3 (7)C38—N3—C39—Hg1−4.3 (8)
C13—C14—C15—C161.3 (11)C23—Hg1—C39—N4132 (2)
C14—C15—C16—C17−179.7 (7)C23—Hg1—C39—N3−43 (3)
C20—C15—C16—C170.8 (10)C39—N3—C40—C410.9 (8)
C14—C15—C16—C11−0.3 (10)C38—N3—C40—C41179.9 (6)
C20—C15—C16—C11−179.7 (6)N3—C40—C41—N40.1 (8)
C12—C11—C16—C17179.2 (6)C39—N4—C41—C40−1.0 (8)
C1—C11—C16—C17−1.7 (10)C42—N4—C41—C40177.6 (6)
C12—C11—C16—C15−0.2 (9)C39—N4—C42—C4334.2 (9)
C1—C11—C16—C15178.8 (6)C41—N4—C42—C43−144.1 (6)
C15—C16—C17—C18−0.9 (11)N4—C42—C43—C44−112.5 (7)
C11—C16—C17—C18179.7 (7)N4—C42—C43—C4868.8 (7)
C16—C17—C18—C190.6 (13)C48—C43—C44—C45−1.3 (10)
C17—C18—C19—C20−0.2 (14)C42—C43—C44—C45180.0 (6)
C18—C19—C20—C150.2 (13)C43—C44—C45—C46−0.5 (12)
C14—C15—C20—C19180.0 (8)C44—C45—C46—C472.3 (13)
C16—C15—C20—C19−0.6 (11)C45—C46—C47—C48−2.2 (12)
C2—O1—C21—C22−71.7 (7)C45—C46—C47—C52176.1 (8)
C23—N1—C22—C21107.3 (7)C46—C47—C48—C430.3 (9)
C24—N1—C22—C21−75.7 (8)C52—C47—C48—C43−178.1 (6)
O1—C21—C22—N1−67.6 (7)C46—C47—C48—C49179.0 (6)
C25—N2—C23—N1−0.7 (7)C52—C47—C48—C490.6 (10)
C26—N2—C23—N1−168.2 (6)C44—C43—C48—C471.3 (9)
C25—N2—C23—Hg1−174.5 (5)C42—C43—C48—C47−180.0 (6)
C26—N2—C23—Hg118.0 (9)C44—C43—C48—C49−177.3 (6)
C24—N1—C23—N2−0.5 (7)C42—C43—C48—C491.5 (9)
C22—N1—C23—N2176.8 (6)C47—C48—C49—C50−0.9 (10)
C24—N1—C23—Hg1173.3 (5)C43—C48—C49—C50177.7 (7)
C22—N1—C23—Hg1−9.4 (9)C48—C49—C50—C51−0.9 (13)
C39—Hg1—C23—N286 (3)C49—C50—C51—C523.1 (15)
C39—Hg1—C23—N1−87 (3)C50—C51—C52—C47−3.4 (15)
C23—N1—C24—C251.6 (8)C48—C47—C52—C511.6 (13)
C22—N1—C24—C25−176.0 (6)C46—C47—C52—C51−176.7 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21—H21A···F11i0.972.543.257 (10)131
C24—H24···F7i0.932.323.217 (12)161
C38—H38B···F3ii0.972.543.423 (9)151
C58—H58B···F8iii0.962.473.26 (2)140
C26—H26A···N6iv0.972.583.320 (9)133
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x+1, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21—H21A···F11i0.972.543.257 (10)131
C24—H24···F7i0.932.323.217 (12)161
C38—H38B···F3ii0.972.543.423 (9)151
C58—H58B···F8iii0.962.473.26 (2)140
C26—H26A···N6iv0.972.583.320 (9)133
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x+1, y+1, z.
Acknowledgements top

The authors thank Hebei Normal University and Hebei Polytechnic University for supporting this work.

references
References top

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Scheele, U. J., Dechert, S. & Meyer, F. (2006). Inorg. Chim. Acta, 359, 4891–4900.

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Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.