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Acta Cryst. (2009). E65, m217    [ doi:10.1107/S1600536809001743 ]

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

W.-Y. Guo and G.-Y. Dong

Abstract top

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.

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

Refinement top

All H atoms were geometrically positioned [C—H= 0.93-0.96 Å] and refined as riding, with Uiso(H) =1.2-1.5Ueq(C). The six F atoms of one hexafluoridophosphate anion show rotational disorder, and they were refined as two groups sharing the same P atom with the occupancies refined to 0.676 (17) and 0.324 (17), respectively. The P—F and F—F distances were restrained to 1.56 (1) and 2.21 (1) Å, respectively. The displacement parameters of the disordered F atoms were also restrained to be approximately isotropic.

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
[Figure 1] 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·C2H3NF(000) = 1992
Mr = 1018.18Dx = 1.791 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.204 (2) ÅCell parameters from 857 reflections
b = 11.433 (3) Åθ = 2.3–22.3°
c = 35.922 (10) ŵ = 4.26 mm−1
β = 92.837 (5)°T = 293 K
V = 3775.7 (17) Å3Block, white
Z = 40.18 × 0.16 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		7729 independent reflections
Radiation source: fine-focus sealed tube5450 reflections with I > 2σ(I)
graphiteRint = 0.062
φ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.448, Tmax = 0.590k = −14→13
21427 measured reflectionsl = −44→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0346P)2 + 0.5948P]
where P = (Fo2 + 2Fc2)/3
7729 reflections(Δ/σ)max = 0.001
552 parametersΔρmax = 0.82 e Å−3
108 restraintsΔρmin = −1.46 e Å−3
Crystal data top
[Hg(C32H30N4O)](PF6)2·C2H3NV = 3775.7 (17) Å3
Mr = 1018.18Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.204 (2) ŵ = 4.26 mm−1
b = 11.433 (3) ÅT = 293 K
c = 35.922 (10) Å0.18 × 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)
Tmin = 0.448, Tmax = 0.590Rint = 0.062
21427 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.101Δρmax = 0.82 e Å−3
S = 1.12Δρmin = −1.46 e Å−3
7729 reflectionsAbsolute structure: ?
552 parametersFlack parameter: ?
108 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Hg10.78607 (3)0.22825 (2)0.087425 (8)0.04048 (10)
N10.6181 (6)0.4642 (5)0.09040 (16)0.0405 (14)
N20.7257 (6)0.4380 (5)0.03912 (17)0.0446 (14)
N30.8152 (6)−0.0190 (5)0.06247 (17)0.0456 (15)
N40.9815 (6)0.0114 (4)0.10573 (16)0.0400 (14)
O10.7511 (5)0.1912 (4)0.01725 (14)0.0562 (14)
C10.7067 (7)0.3919 (6)0.07289 (18)0.0356 (15)
C20.8659 (7)0.0599 (5)0.08832 (19)0.0364 (16)
C30.5818 (8)0.5568 (6)0.0675 (2)0.053 (2)
H30.52180.61930.07300.063*
C40.6487 (8)0.5400 (6)0.0362 (2)0.055 (2)
H40.64390.58940.01560.066*
C50.5474 (7)0.4420 (6)0.1255 (2)0.0472 (18)
H5A0.45520.40330.11980.057*
H5B0.52640.51670.13690.057*
C60.6331 (7)0.3695 (6)0.15335 (19)0.0401 (16)
C70.5962 (8)0.2543 (6)0.1577 (2)0.0507 (19)
H70.52260.22190.14230.061*
C80.6666 (9)0.1856 (7)0.1845 (2)0.059 (2)
H80.64060.10740.18680.071*
C90.7719 (9)0.2303 (8)0.2072 (2)0.064 (2)
H90.81770.18240.22510.077*
C100.8150 (7)0.3472 (7)0.2046 (2)0.051 (2)
C110.7459 (7)0.4197 (6)0.1767 (2)0.0437 (17)
C120.7841 (8)0.5398 (7)0.1752 (3)0.062 (2)
H120.73930.58860.15740.075*
C130.8879 (10)0.5835 (9)0.2004 (3)0.083 (3)
H130.91330.66210.19930.100*
C140.9563 (11)0.5114 (11)0.2276 (3)0.093 (4)
H141.02520.54290.24460.111*
C150.9225 (9)0.3971 (10)0.2293 (3)0.077 (3)
H150.97070.34990.24710.093*
C160.8153 (8)0.3898 (7)0.0104 (2)0.056 (2)
H16A0.90990.36980.02180.068*
H16B0.83010.4498−0.00810.068*
C170.7529 (10)0.2839 (7)−0.0088 (2)0.065 (2)
H17A0.65490.3001−0.01860.077*
H17B0.81160.2625−0.02940.077*
C180.7271 (9)0.0771 (7)0.0039 (2)0.063 (2)
H18A0.81340.0488−0.00760.076*
H18B0.64730.0771−0.01480.076*
C190.6917 (8)−0.0015 (7)0.0353 (3)0.066 (3)
H19A0.61060.03140.04800.080*
H19B0.6612−0.07690.02520.080*
C200.8994 (8)−0.1176 (6)0.0652 (2)0.058 (2)
H200.8875−0.18500.05090.069*
C211.0027 (8)−0.0991 (6)0.0926 (2)0.052 (2)
H211.0745−0.15150.10090.062*
C221.0724 (7)0.0685 (5)0.13471 (18)0.0384 (16)
H22A1.06080.15250.13200.046*
H22B1.17330.05020.13070.046*
C231.0407 (7)0.0353 (6)0.1741 (2)0.0405 (17)
C240.9391 (8)−0.0466 (6)0.1815 (2)0.052 (2)
H240.8897−0.08610.16210.063*
C250.9092 (10)−0.0711 (7)0.2189 (3)0.068 (3)
H250.8407−0.12810.22380.082*
C260.9761 (10)−0.0150 (8)0.2475 (3)0.072 (3)
H260.9535−0.03260.27180.087*
C271.0806 (9)0.0706 (8)0.2406 (2)0.060 (2)
C281.1169 (7)0.0954 (6)0.2036 (2)0.0460 (18)
C291.2233 (8)0.1818 (7)0.1976 (2)0.060 (2)
H291.25190.19680.17360.072*
C301.2843 (9)0.2434 (8)0.2272 (3)0.079 (3)
H301.35320.30060.22290.095*
C311.2465 (12)0.2229 (11)0.2629 (3)0.099 (4)
H311.28740.26750.28240.118*
C321.1476 (11)0.1357 (10)0.2701 (3)0.086 (3)
H321.12510.11990.29460.103*
P10.2485 (2)0.25046 (17)0.05306 (6)0.0565 (6)
F10.0984 (6)0.2867 (5)0.07142 (18)0.1065 (19)
F20.2972 (6)0.3825 (4)0.05426 (15)0.0916 (17)
F30.3110 (7)0.2339 (5)0.09374 (17)0.121 (2)
F40.1948 (7)0.1215 (4)0.05251 (18)0.121 (2)
F50.1711 (8)0.2736 (6)0.01355 (16)0.126 (2)
F60.3852 (7)0.2175 (6)0.0336 (3)0.168 (4)
P20.4756 (3)0.85219 (19)0.12903 (7)0.0684 (7)
F70.4630 (11)0.7192 (5)0.1395 (2)0.098 (4)0.676 (17)
F80.5350 (14)0.8758 (9)0.1705 (2)0.142 (6)0.676 (17)
F90.3183 (8)0.8715 (10)0.1421 (4)0.160 (7)0.676 (17)
F100.4176 (16)0.8252 (9)0.0891 (2)0.162 (7)0.676 (17)
F110.6340 (8)0.8292 (11)0.1181 (4)0.167 (7)0.676 (17)
F120.4887 (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)
C330.0674 (11)0.5635 (10)0.1002 (4)0.093 (4)
C340.1418 (12)0.5175 (13)0.1326 (4)0.151 (6)
H34A0.15990.57910.15030.226*
H34B0.23260.48410.12590.226*
H34C0.08310.45820.14330.226*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.04380 (15)0.03932 (15)0.03823 (15)0.00852 (13)0.00125 (10)0.00183 (15)
N10.042 (3)0.040 (3)0.040 (4)0.007 (3)0.000 (3)0.001 (3)
N20.053 (4)0.043 (3)0.038 (4)0.002 (3)0.002 (3)0.010 (3)
N30.047 (3)0.045 (4)0.044 (4)0.002 (3)−0.001 (3)−0.006 (3)
N40.039 (3)0.036 (3)0.045 (4)0.004 (2)0.000 (3)0.002 (3)
O10.080 (4)0.049 (3)0.038 (3)0.005 (3)−0.003 (3)−0.004 (2)
C10.038 (4)0.045 (4)0.023 (4)0.004 (3)−0.006 (3)0.006 (3)
C20.036 (4)0.035 (4)0.038 (4)−0.001 (3)0.003 (3)0.004 (3)
C30.064 (5)0.038 (4)0.055 (5)0.011 (3)0.004 (4)0.012 (4)
C40.067 (5)0.052 (5)0.047 (5)0.009 (4)0.004 (4)0.020 (4)
C50.045 (4)0.045 (4)0.052 (5)0.015 (3)0.007 (4)−0.005 (4)
C60.040 (4)0.047 (4)0.034 (4)0.013 (3)0.006 (3)−0.003 (3)
C70.058 (4)0.043 (5)0.051 (5)−0.002 (3)0.012 (4)−0.007 (4)
C80.071 (5)0.043 (4)0.065 (6)0.005 (4)0.013 (5)0.006 (4)
C90.062 (5)0.069 (6)0.062 (6)0.029 (5)0.015 (4)0.019 (5)
C100.034 (4)0.076 (6)0.043 (5)0.015 (4)0.001 (3)−0.004 (4)
C110.045 (4)0.053 (5)0.034 (4)0.010 (3)0.010 (3)−0.002 (4)
C120.061 (5)0.055 (5)0.071 (6)−0.003 (4)0.009 (5)−0.006 (5)
C130.070 (6)0.085 (7)0.096 (9)−0.028 (5)0.020 (6)−0.039 (6)
C140.073 (7)0.138 (10)0.065 (8)−0.012 (7)−0.010 (6)−0.047 (7)
C150.059 (6)0.112 (8)0.060 (6)0.017 (5)−0.006 (5)−0.019 (6)
C160.061 (5)0.058 (5)0.051 (5)0.002 (4)0.014 (4)0.018 (4)
C170.085 (6)0.070 (6)0.039 (5)0.025 (5)0.006 (4)0.010 (5)
C180.072 (6)0.063 (6)0.053 (6)0.004 (4)−0.020 (5)−0.009 (5)
C190.057 (5)0.057 (5)0.083 (7)−0.001 (4)−0.021 (5)−0.016 (5)
C200.069 (5)0.039 (4)0.065 (6)0.009 (4)0.000 (5)−0.013 (4)
C210.060 (5)0.038 (4)0.057 (5)0.015 (3)−0.003 (4)−0.004 (4)
C220.039 (4)0.040 (4)0.036 (4)0.003 (3)−0.002 (3)0.002 (3)
C230.045 (4)0.036 (4)0.042 (4)0.011 (3)0.011 (3)0.014 (3)
C240.054 (5)0.047 (4)0.056 (5)0.012 (4)0.011 (4)0.010 (4)
C250.075 (6)0.061 (6)0.070 (7)0.013 (4)0.025 (5)0.024 (5)
C260.083 (7)0.096 (7)0.041 (6)0.033 (6)0.024 (5)0.031 (5)
C270.057 (5)0.090 (6)0.035 (5)0.035 (5)0.011 (4)0.010 (5)
C280.037 (4)0.062 (5)0.039 (5)0.016 (3)0.001 (3)0.001 (4)
C290.046 (4)0.081 (6)0.052 (5)−0.001 (4)0.001 (4)−0.008 (5)
C300.061 (5)0.101 (7)0.074 (7)0.006 (5)−0.015 (5)−0.031 (6)
C310.086 (7)0.149 (11)0.058 (7)0.038 (7)−0.028 (6)−0.054 (7)
C320.081 (7)0.142 (10)0.034 (5)0.047 (7)0.001 (5)−0.001 (6)
P10.0708 (13)0.0512 (15)0.0477 (12)−0.0113 (10)0.0043 (10)0.0032 (10)
F10.093 (4)0.110 (4)0.119 (5)0.002 (3)0.026 (4)0.010 (4)
F20.134 (5)0.059 (3)0.081 (4)−0.030 (3)−0.003 (3)0.009 (3)
F30.151 (6)0.117 (5)0.088 (5)−0.046 (4)−0.053 (4)0.043 (4)
F40.188 (6)0.060 (3)0.120 (5)−0.041 (4)0.051 (5)−0.020 (3)
F50.150 (6)0.161 (6)0.066 (4)−0.056 (4)−0.020 (4)0.025 (4)
F60.110 (5)0.127 (5)0.277 (11)0.016 (4)0.108 (6)0.001 (6)
P20.0722 (15)0.0515 (15)0.0814 (19)0.0090 (11)0.0026 (14)−0.0021 (13)
F70.128 (9)0.046 (5)0.121 (9)0.015 (5)0.034 (7)−0.006 (5)
F80.202 (15)0.134 (10)0.085 (8)−0.020 (9)−0.058 (9)−0.010 (7)
F90.091 (8)0.187 (13)0.202 (17)0.079 (8)−0.004 (9)−0.024 (12)
F100.267 (19)0.130 (10)0.080 (8)0.018 (12)−0.080 (10)−0.015 (7)
F110.083 (8)0.218 (16)0.204 (17)−0.027 (8)0.053 (9)0.003 (13)
F120.32 (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)
N50.136 (9)0.095 (7)0.127 (10)0.007 (7)0.004 (8)−0.008 (7)
C330.060 (7)0.101 (9)0.117 (11)0.010 (6)−0.003 (7)−0.043 (8)
C340.081 (8)0.253 (17)0.116 (12)0.056 (10)−0.013 (8)−0.055 (12)
Geometric parameters (Å, °) top
Hg1—C22.060 (6)C19—H19A0.9700
Hg1—C12.066 (6)C19—H19B0.9700
Hg1—O12.561 (5)C20—C211.349 (10)
N1—C11.340 (8)C20—H200.9300
N1—C31.371 (8)C21—H210.9300
N1—C51.471 (9)C22—C231.508 (9)
N2—C11.342 (8)C22—H22A0.9700
N2—C41.366 (8)C22—H22B0.9700
N2—C161.459 (9)C23—C241.358 (9)
N3—C21.360 (8)C23—C281.419 (10)
N3—C201.369 (8)C24—C251.413 (11)
N3—C191.476 (9)C24—H240.9300
N4—C21.328 (8)C25—C261.335 (12)
N4—C211.366 (8)C25—H250.9300
N4—C221.458 (8)C26—C271.403 (12)
O1—C181.403 (8)C26—H260.9300
O1—C171.414 (8)C27—C321.412 (12)
C3—C41.324 (10)C27—C281.416 (10)
C3—H30.9300C28—C291.415 (10)
C4—H40.9300C29—C301.374 (11)
C5—C61.494 (9)C29—H290.9300
C5—H5A0.9700C30—C311.365 (14)
C5—H5B0.9700C30—H300.9300
C6—C71.370 (9)C31—C321.383 (14)
C6—C111.423 (9)C31—H310.9300
C7—C81.379 (10)C32—H320.9300
C7—H70.9300P1—F61.516 (6)
C8—C91.336 (11)P1—F41.555 (5)
C8—H80.9300P1—F31.555 (6)
C9—C101.399 (11)P1—F21.575 (5)
C9—H90.9300P1—F51.579 (6)
C10—C151.416 (11)P1—F11.614 (6)
C10—C111.427 (10)P2—F8'1.536 (8)
C11—C121.419 (10)P2—F121.537 (6)
C12—C131.377 (11)P2—F101.538 (6)
C12—H120.9300P2—F7'1.539 (8)
C13—C141.405 (14)P2—F111.551 (6)
C13—H130.9300P2—F11'1.555 (8)
C14—C151.346 (13)P2—F91.560 (7)
C14—H140.9300P2—F9'1.561 (8)
C15—H150.9300P2—F71.572 (6)
C16—C171.495 (10)P2—F10'1.582 (8)
C16—H16A0.9700P2—F12'1.585 (8)
C16—H16B0.9700P2—F81.585 (6)
C17—H17A0.9700N5—C331.141 (13)
C17—H17B0.9700C33—C341.421 (16)
C18—C191.489 (11)C34—H34A0.9600
C18—H18A0.9700C34—H34B0.9600
C18—H18B0.9700C34—H34C0.9600
C2—Hg1—C1166.3 (3)C24—C25—H25118.9
C2—Hg1—O183.6 (2)C25—C26—C27119.5 (8)
C1—Hg1—O182.9 (2)C25—C26—H26120.2
C1—N1—C3109.3 (6)C27—C26—H26120.2
C1—N1—C5127.0 (5)C26—C27—C32120.9 (9)
C3—N1—C5122.9 (6)C26—C27—C28120.1 (8)
C1—N2—C4108.4 (6)C32—C27—C28119.0 (9)
C1—N2—C16126.4 (6)C29—C28—C27118.8 (8)
C4—N2—C16125.2 (6)C29—C28—C23123.0 (7)
C2—N3—C20108.8 (6)C27—C28—C23118.3 (7)
C2—N3—C19126.1 (6)C30—C29—C28119.9 (9)
C20—N3—C19125.1 (6)C30—C29—H29120.1
C2—N4—C21110.4 (6)C28—C29—H29120.1
C2—N4—C22124.6 (5)C31—C30—C29121.8 (10)
C21—N4—C22125.1 (6)C31—C30—H30119.1
C18—O1—C17118.5 (6)C29—C30—H30119.1
C18—O1—Hg1120.0 (4)C30—C31—C32120.0 (9)
C17—O1—Hg1121.5 (4)C30—C31—H31120.0
N1—C1—N2106.9 (5)C32—C31—H31120.0
N1—C1—Hg1131.0 (5)C31—C32—C27120.5 (9)
N2—C1—Hg1121.6 (5)C31—C32—H32119.8
N4—C2—N3106.6 (5)C27—C32—H32119.8
N4—C2—Hg1132.4 (5)F6—P1—F491.7 (4)
N3—C2—Hg1119.9 (5)F6—P1—F397.2 (5)
C4—C3—N1106.8 (6)F4—P1—F390.0 (3)
C4—C3—H3126.6F6—P1—F290.5 (3)
N1—C3—H3126.6F4—P1—F2177.8 (4)
C3—C4—N2108.6 (7)F3—P1—F289.9 (3)
C3—C4—H4125.7F6—P1—F588.6 (5)
N2—C4—H4125.7F4—P1—F591.1 (3)
N1—C5—C6115.4 (5)F3—P1—F5174.1 (4)
N1—C5—H5A108.4F2—P1—F588.8 (3)
C6—C5—H5A108.4F6—P1—F1176.7 (5)
N1—C5—H5B108.4F4—P1—F188.3 (3)
C6—C5—H5B108.4F3—P1—F186.1 (4)
H5A—C5—H5B107.5F2—P1—F189.5 (3)
C7—C6—C11119.9 (6)F5—P1—F188.1 (4)
C7—C6—C5119.0 (7)F8'—P2—F1284.9 (9)
C11—C6—C5121.0 (6)F8'—P2—F10128.3 (8)
C6—C7—C8121.1 (7)F12—P2—F1091.2 (4)
C6—C7—H7119.5F8'—P2—F7'92.3 (6)
C8—C7—H7119.5F12—P2—F7'127.2 (9)
C9—C8—C7120.6 (7)F10—P2—F7'128.3 (10)
C9—C8—H8119.7F8'—P2—F11140.5 (8)
C7—C8—H8119.7F12—P2—F1191.5 (5)
C8—C9—C10121.7 (7)F10—P2—F1191.0 (5)
C8—C9—H9119.2F7'—P2—F1159.3 (9)
C10—C9—H9119.2F8'—P2—F11'91.6 (6)
C9—C10—C15122.4 (8)F12—P2—F11'36.5 (8)
C9—C10—C11118.9 (7)F10—P2—F11'114.5 (8)
C15—C10—C11118.7 (8)F7'—P2—F11'91.2 (6)
C12—C11—C6122.9 (7)F11—P2—F11'64.6 (8)
C12—C11—C10119.1 (7)F8'—P2—F937.4 (8)
C6—C11—C10117.8 (7)F12—P2—F990.6 (5)
C13—C12—C11119.4 (8)F10—P2—F991.4 (4)
C13—C12—H12120.3F7'—P2—F9117.5 (9)
C11—C12—H12120.3F11—P2—F9176.7 (5)
C12—C13—C14121.2 (9)F11'—P2—F9116.1 (8)
C12—C13—H13119.4F8'—P2—F9'91.2 (6)
C14—C13—H13119.4F12—P2—F9'142.0 (9)
C15—C14—C13120.3 (9)F10—P2—F9'62.3 (9)
C15—C14—H14119.8F7'—P2—F9'90.6 (6)
C13—C14—H14119.8F11—P2—F9'114.1 (8)
C14—C15—C10121.2 (9)F11'—P2—F9'176.7 (7)
C14—C15—H15119.4F9—P2—F9'65.3 (8)
C10—C15—H15119.4F8'—P2—F794.1 (8)
N2—C16—C17114.5 (6)F12—P2—F7178.6 (5)
N2—C16—H16A108.6F10—P2—F790.2 (4)
C17—C16—H16A108.6F7'—P2—F751.9 (10)
N2—C16—H16B108.6F11—P2—F788.7 (4)
C17—C16—H16B108.6F11'—P2—F7142.7 (9)
H16A—C16—H16B107.6F9—P2—F789.1 (4)
O1—C17—C16108.5 (6)F9'—P2—F738.8 (9)
O1—C17—H17A110.0F8'—P2—F10'177.4 (7)
C16—C17—H17A110.0F12—P2—F10'93.8 (8)
O1—C17—H17B110.0F10—P2—F10'49.4 (7)
C16—C17—H17B110.0F7'—P2—F10'90.3 (5)
H17A—C17—H17B108.4F11—P2—F10'41.7 (7)
O1—C18—C19109.8 (7)F11'—P2—F10'88.7 (5)
O1—C18—H18A109.7F9—P2—F10'140.6 (8)
C19—C18—H18A109.7F9'—P2—F10'88.5 (5)
O1—C18—H18B109.7F7—P2—F10'87.2 (7)
C19—C18—H18B109.7F8'—P2—F12'89.8 (5)
H18A—C18—H18B108.2F12—P2—F12'53.5 (8)
N3—C19—C18113.1 (6)F10—P2—F12'49.7 (8)
N3—C19—H19A109.0F7'—P2—F12'177.9 (7)
C18—C19—H19A109.0F11—P2—F12'119.2 (8)
N3—C19—H19B109.0F11'—P2—F12'89.3 (5)
C18—C19—H19B109.0F9—P2—F12'64.1 (8)
H19A—C19—H19B107.8F9'—P2—F12'88.8 (5)
C21—C20—N3107.4 (6)F7—P2—F12'127.5 (9)
C21—C20—H20126.3F10'—P2—F12'87.7 (5)
N3—C20—H20126.3F8'—P2—F851.9 (8)
C20—C21—N4106.8 (6)F12—P2—F890.6 (4)
C20—C21—H21126.6F10—P2—F8178.2 (5)
N4—C21—H21126.6F7'—P2—F850.3 (10)
N4—C22—C23115.2 (5)F11—P2—F888.9 (4)
N4—C22—H22A108.5F11'—P2—F867.0 (8)
C23—C22—H22A108.5F9—P2—F888.6 (4)
N4—C22—H22B108.5F9'—P2—F8116.2 (9)
C23—C22—H22B108.5F7—P2—F888.1 (4)
H22A—C22—H22B107.5F10'—P2—F8130.4 (8)
C24—C23—C28120.5 (7)F12'—P2—F8131.7 (9)
C24—C23—C22121.6 (7)N5—C33—C34175.2 (15)
C28—C23—C22117.8 (6)C33—C34—H34A109.5
C23—C24—C25119.4 (8)C33—C34—H34B109.5
C23—C24—H24120.3H34A—C34—H34B109.5
C25—C24—H24120.3C33—C34—H34C109.5
C26—C25—C24122.2 (8)H34A—C34—H34C109.5
C26—C25—H25118.9H34B—C34—H34C109.5
C2—Hg1—O1—C1828.4 (5)C9—C10—C11—C61.7 (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—C13175.7 (7)
C1—Hg1—O1—C1725.3 (5)C10—C11—C12—C130.8 (11)
C3—N1—C1—N2−0.3 (7)C11—C12—C13—C14−0.3 (14)
C5—N1—C1—N2169.5 (6)C12—C13—C14—C150.9 (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—N10.5 (7)C11—C10—C15—C142.3 (13)
C16—N2—C1—N1179.3 (6)C1—N2—C16—C1773.3 (9)
C4—N2—C1—Hg1173.4 (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—N1151.3 (9)Hg1—O1—C17—C1614.7 (8)
O1—Hg1—C1—N1142.7 (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—C1913.4 (8)
C21—N4—C2—N3−2.4 (8)C2—N3—C19—C1874.7 (10)
C22—N4—C2—N3177.6 (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—Hg110.3 (10)C2—N3—C20—C21−0.5 (9)
C20—N3—C2—N41.8 (8)C19—N3—C20—C21178.4 (7)
C19—N3—C2—N4−177.1 (7)N3—C20—C21—N4−0.9 (9)
C20—N3—C2—Hg1170.9 (5)C2—N4—C21—C202.1 (9)
C19—N3—C2—Hg1−8.0 (9)C22—N4—C21—C20−177.9 (7)
C1—Hg1—C2—N4127.6 (10)C2—N4—C22—C2399.1 (7)
O1—Hg1—C2—N4136.1 (7)C21—N4—C22—C23−81.0 (8)
C1—Hg1—C2—N3−38.3 (13)N4—C22—C23—C243.1 (9)
O1—Hg1—C2—N3−29.7 (5)N4—C22—C23—C28−174.7 (5)
C1—N1—C3—C40.1 (8)C28—C23—C24—C250.4 (10)
C5—N1—C3—C4−170.3 (6)C22—C23—C24—C25−177.4 (6)
N1—C3—C4—N20.2 (9)C23—C24—C25—C261.0 (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—C32176.6 (8)
C1—N1—C5—C633.7 (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—C292.3 (10)
N1—C5—C6—C1180.6 (8)C26—C27—C28—C232.6 (10)
C11—C6—C7—C80.1 (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—C90.6 (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—C15177.6 (8)C22—C23—C28—C27175.7 (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—C30174.6 (7)
C5—C6—C11—C120.0 (10)C28—C29—C30—C310.8 (13)
C7—C6—C11—C10−1.3 (10)C29—C30—C31—C322.0 (15)
C5—C6—C11—C10175.0 (6)C30—C31—C32—C27−2.6 (14)
C9—C10—C11—C12176.9 (7)C26—C27—C32—C31−177.6 (8)
C15—C10—C11—C12−1.7 (10)C28—C27—C32—C310.4 (12)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···F30.972.503.384 (9)151
C5—H5B···F70.972.393.307 (9)157
C18—H18A···F4i0.972.533.150 (10)122
C22—H22B···F9ii0.972.463.195 (11)132
C24—H24···N40.932.502.847 (9)103
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···F30.972.503.384 (9)151
C5—H5B···F70.972.393.307 (9)157
C18—H18A···F4i0.972.533.150 (10)122
C22—H22B···F9ii0.972.463.195 (11)132
C24—H24···N40.932.502.847 (9)103
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z.
Acknowledgements top

The authors thank Shanxi Normal University for supporting of this work.

references
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