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Acta Cryst. (2010). E66, o2695    [ doi:10.1107/S1600536810038432 ]

4-Benzyl-4-methylmorpholinium hexafluorophosphate

Q. Su, H.-J. Zang, T. Xu and Y.-L. Ren

Abstract top

In the title compound, C12H18NO+·PF6-, the asymmetric unit consists of two cation-anion pairs. The six F atoms of one anion are disordered over two sets of sites in a 0.592 (6):0.408 (6) ratio. The morpholinium rings adopt chair conformations.

Comment top

Room-temperature ionic liquids (RTILs) consist of organic cation and anion which exist in liquid state at room temperature or below 100 °C. They are widely used in various fields of electrochemistry and chemistry because of their unique properties such as nonvolatility and nonflammability. In particular, ILs based on the morpholinium cation are favored becaused of their low cost, easy synthesis, and electrochemical stability (Kim et al., 2006). So far, only a few crystallographic studies have been performed on salts. We report here a new example structure of this class.

The molecular structure of (I) is shown in Fig. 1. For the title compound two crystallographically independent molecules are present in the asymmetric unit of the cell. The morpholine unit adopts a chair conformation. Disorder model was introduced for the anion, in which the six fluorine atoms are all disordered over two positions. The bond distances and angles in the cation are normal within experimental error.

Related literature top

Ionic liquids based on the morpholinium cation are favored becaused of their low cost, easy synthesis, and electrochemical stability, see: Kim et al. (2006).

Experimental top

To a magnetically stirred solution of the 4-benzyl-4-methylmorpholinium chloride (2.29 g, 10 mmol) in acetonitrile (20 ml) was added potassium hexafluorophosphate (1.86 g, 10 mmol). The mixture was stirred at room temperrature for 72 h, and the KCl filtered from the reaction mixture. The solvent was removed under reduced pressure. The residue was washed by ether and then recrystallized from hot ethanol to afford the product. A single-crystal was obtained by slow evaporation of a EtOH solution.

Refinement top

The H atoms bonded to C atoms were included in the refinement in the riding model approximation, with C–H = 0.93–0.97 Å and Uiso (H) = 1.2 Ueq (C atom). For the H atoms attached to C atoms of methyl groups, their Uiso(H) =1.5Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the Structure of (I), Showing the atom-numbering scheme. Dispacement ellipsoids are drawn at the 30% probability level.
4-Benzyl-4-methylmorpholinium hexafluorophosphate top
Crystal data top
C12H18NO+·PF6−Z = 4
Mr = 337.24F(000) = 696
Triclinic, P1Dx = 1.550 Mg m−3
a = 9.7268 (14) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.7183 (16) ÅCell parameters from 4804 reflections
c = 14.537 (2) Åθ = 1.5–27.2°
α = 104.307 (5)°µ = 0.26 mm−1
β = 96.816 (8)°T = 113 K
γ = 95.633 (7)°Block, colorless
V = 1445.3 (4) Å30.22 × 0.14 × 0.12 mm
Data collection top
Rigaku Saturn
diffractometer		6387 independent reflections
Radiation source: rotating anode4730 reflections with I > 2σ(I)
confocalRint = 0.043
Detector resolution: 14.63 pixels mm-1θmax = 27.2°, θmin = 1.5°
ω scansh = −12→12
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −13→13
Tmin = 0.946, Tmax = 0.970l = −18→18
17415 measured reflections
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0518P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
6387 reflectionsΔρmax = 0.53 e Å−3
401 parametersΔρmin = −0.40 e Å−3
84 restraintsExtinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0123 (11)
Crystal data top
C12H18NO+·PF6−γ = 95.633 (7)°
Mr = 337.24V = 1445.3 (4) Å3
Triclinic, P1Z = 4
a = 9.7268 (14) ÅMo Kα radiation
b = 10.7183 (16) ŵ = 0.26 mm−1
c = 14.537 (2) ÅT = 113 K
α = 104.307 (5)°0.22 × 0.14 × 0.12 mm
β = 96.816 (8)°
Data collection top
Rigaku Saturn
diffractometer		6387 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		4730 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.970Rint = 0.043
17415 measured reflectionsθmax = 27.2°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.53 e Å−3
S = 1.03Δρmin = −0.40 e Å−3
6387 reflectionsAbsolute structure: ?
401 parametersFlack parameter: ?
84 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)
P10.30855 (6)0.37650 (5)0.09741 (4)0.02340 (16)
P20.78163 (6)0.24754 (6)0.46477 (4)0.02855 (17)
F10.42358 (14)0.39964 (13)0.03267 (9)0.0368 (4)
F20.40636 (15)0.46701 (15)0.19023 (9)0.0463 (4)
F30.23988 (14)0.49934 (12)0.07859 (9)0.0342 (3)
F40.20934 (16)0.28651 (14)0.00513 (10)0.0477 (4)
F50.37474 (17)0.25367 (14)0.11626 (10)0.0485 (4)
F60.19177 (15)0.35492 (14)0.16311 (10)0.0449 (4)
F7'0.8866 (8)0.1865 (7)0.5320 (5)0.0485 (9)0.592 (6)
F8'0.8069 (6)0.1427 (5)0.3741 (3)0.0583 (12)0.592 (6)
F9'0.6552 (6)0.1530 (5)0.4805 (4)0.0444 (11)0.592 (6)
F10'0.7621 (6)0.3542 (5)0.5615 (4)0.0595 (14)0.592 (6)
F11'0.9139 (4)0.3438 (5)0.4548 (4)0.0648 (13)0.592 (6)
F12'0.6806 (7)0.3126 (7)0.4031 (6)0.0322 (4)0.592 (6)
F70.8809 (11)0.1709 (11)0.5169 (8)0.0485 (9)0.408 (6)
F80.7411 (7)0.1201 (7)0.3742 (5)0.0583 (12)0.408 (6)
F90.6530 (9)0.1932 (7)0.5062 (6)0.0444 (11)0.408 (6)
F100.8134 (9)0.3697 (7)0.5478 (6)0.0595 (14)0.408 (6)
F110.9009 (7)0.2907 (8)0.4109 (5)0.0648 (13)0.408 (6)
F120.6762 (11)0.3186 (11)0.4054 (8)0.0322 (4)0.408 (6)
O11.00560 (16)0.81093 (14)0.22635 (11)0.0328 (4)
O20.27675 (18)0.27512 (15)0.54849 (10)0.0333 (4)
N10.85004 (17)0.55784 (16)0.20963 (12)0.0205 (4)
N20.23494 (18)0.16209 (16)0.34181 (12)0.0215 (4)
C10.9767 (2)0.5774 (2)0.16140 (15)0.0235 (5)
H1A0.94590.58450.09570.028*
H1B1.02720.50070.15590.028*
C21.0748 (2)0.6979 (2)0.21631 (17)0.0295 (5)
H2A1.11040.68880.28070.035*
H2B1.15560.70760.18200.035*
C30.8918 (2)0.8002 (2)0.27847 (16)0.0304 (5)
H3A0.84570.87970.28610.037*
H3B0.92760.79280.34330.037*
C40.7860 (2)0.6831 (2)0.22778 (16)0.0262 (5)
H4A0.74350.69500.16570.031*
H4B0.71070.67690.26730.031*
C50.7400 (2)0.4531 (2)0.14237 (15)0.0234 (5)
H5A0.65360.45130.17210.028*
H5B0.71800.47830.08170.028*
C60.7801 (2)0.3181 (2)0.11851 (15)0.0237 (5)
C70.7297 (2)0.2279 (2)0.16439 (17)0.0317 (5)
H70.67610.25400.21470.038*
C80.7564 (3)0.1000 (2)0.13772 (19)0.0406 (6)
H80.72150.03910.16970.049*
C90.8342 (3)0.0617 (2)0.0645 (2)0.0433 (7)
H90.8526−0.02570.04570.052*
C100.8852 (3)0.1513 (3)0.01851 (19)0.0415 (7)
H100.93940.1252−0.03140.050*
C110.8581 (2)0.2777 (2)0.04457 (16)0.0314 (6)
H110.89270.33800.01200.038*
C120.8884 (2)0.5197 (2)0.30086 (14)0.0262 (5)
H12A0.93620.44230.28740.039*
H12B0.80350.50080.32790.039*
H12C0.95050.59120.34700.039*
C130.2326 (2)0.3049 (2)0.38787 (16)0.0275 (5)
H13A0.13510.32040.39430.033*
H13B0.26750.35680.34570.033*
C140.3215 (3)0.3497 (2)0.48603 (16)0.0321 (6)
H14A0.42040.34100.47920.038*
H14B0.31510.44260.51440.038*
C150.2877 (3)0.1415 (2)0.50940 (15)0.0297 (5)
H15A0.25950.09120.55430.036*
H15B0.38610.13140.50180.036*
C160.1962 (2)0.0883 (2)0.41301 (15)0.0245 (5)
H16A0.2060−0.00450.38770.029*
H16B0.09720.09430.42120.029*
C170.3792 (2)0.1439 (2)0.31398 (15)0.0233 (5)
H17A0.40050.20210.27280.028*
H17B0.44860.17240.37310.028*
C180.3991 (2)0.0077 (2)0.26190 (15)0.0222 (5)
C190.4247 (2)−0.0859 (2)0.31083 (15)0.0259 (5)
H190.4245−0.06610.37820.031*
C200.4506 (2)−0.2080 (2)0.26217 (16)0.0305 (5)
H200.4643−0.27230.29590.037*
C210.4564 (2)−0.2362 (2)0.16470 (16)0.0281 (5)
H210.4756−0.31930.13160.034*
C220.4341 (2)−0.1434 (2)0.11574 (16)0.0294 (5)
H220.4394−0.16220.04900.035*
C230.4040 (2)−0.0223 (2)0.16372 (15)0.0278 (5)
H230.38660.04050.12920.033*
C240.1262 (2)0.1182 (2)0.25385 (15)0.0289 (5)
H24A0.12210.02440.22690.043*
H24B0.15080.16370.20610.043*
H24C0.03500.13800.27120.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0243 (3)0.0239 (3)0.0254 (3)0.0053 (2)0.0057 (3)0.0112 (2)
P20.0243 (3)0.0329 (4)0.0321 (4)0.0022 (3)0.0026 (3)0.0165 (3)
F10.0325 (8)0.0462 (9)0.0401 (8)0.0109 (7)0.0181 (7)0.0186 (7)
F20.0434 (9)0.0533 (10)0.0331 (8)0.0054 (7)−0.0054 (7)0.0000 (7)
F30.0361 (8)0.0347 (8)0.0433 (8)0.0166 (6)0.0148 (7)0.0229 (6)
F40.0494 (10)0.0389 (9)0.0444 (9)−0.0092 (7)−0.0088 (7)0.0046 (7)
F50.0645 (11)0.0424 (9)0.0555 (10)0.0321 (8)0.0210 (8)0.0288 (8)
F60.0417 (9)0.0553 (10)0.0563 (10)0.0147 (7)0.0240 (8)0.0378 (8)
F7'0.0379 (11)0.0567 (19)0.058 (2)0.0078 (12)−0.0078 (12)0.0350 (18)
F8'0.076 (3)0.070 (2)0.0396 (10)0.046 (2)0.020 (2)0.0151 (12)
F9'0.0339 (9)0.047 (3)0.057 (3)−0.0077 (18)0.0016 (16)0.031 (2)
F10'0.084 (4)0.0476 (16)0.0360 (16)0.016 (2)−0.0128 (19)−0.0014 (13)
F11'0.0255 (12)0.083 (3)0.101 (4)−0.0102 (18)0.000 (2)0.065 (3)
F12'0.0292 (8)0.0341 (10)0.0355 (8)0.0051 (6)−0.0023 (7)0.0162 (7)
F70.0379 (11)0.0567 (19)0.058 (2)0.0078 (12)−0.0078 (12)0.0350 (18)
F80.076 (3)0.070 (2)0.0396 (10)0.046 (2)0.020 (2)0.0151 (12)
F90.0339 (9)0.047 (3)0.057 (3)−0.0077 (18)0.0016 (16)0.031 (2)
F100.084 (4)0.0476 (16)0.0360 (16)0.016 (2)−0.0128 (19)−0.0014 (13)
F110.0255 (12)0.083 (3)0.101 (4)−0.0102 (18)0.000 (2)0.065 (3)
F120.0292 (8)0.0341 (10)0.0355 (8)0.0051 (6)−0.0023 (7)0.0162 (7)
O10.0361 (10)0.0228 (9)0.0409 (10)0.0034 (7)0.0130 (8)0.0079 (7)
O20.0499 (11)0.0283 (9)0.0239 (8)0.0131 (8)0.0112 (8)0.0051 (7)
N10.0187 (9)0.0237 (10)0.0204 (9)0.0049 (7)0.0041 (8)0.0067 (7)
N20.0240 (10)0.0193 (9)0.0218 (9)0.0034 (7)0.0019 (8)0.0069 (7)
C10.0192 (11)0.0264 (12)0.0259 (12)0.0048 (9)0.0083 (9)0.0057 (9)
C20.0245 (13)0.0277 (12)0.0353 (13)0.0032 (10)0.0090 (10)0.0041 (10)
C30.0327 (14)0.0276 (12)0.0336 (13)0.0102 (10)0.0116 (11)0.0073 (10)
C40.0249 (12)0.0272 (12)0.0296 (12)0.0107 (10)0.0064 (10)0.0092 (10)
C50.0174 (11)0.0311 (12)0.0212 (11)0.0019 (9)0.0002 (9)0.0076 (9)
C60.0173 (11)0.0285 (12)0.0222 (11)−0.0007 (9)−0.0019 (9)0.0046 (9)
C70.0268 (13)0.0339 (13)0.0311 (13)−0.0031 (10)−0.0029 (10)0.0086 (10)
C80.0378 (15)0.0310 (14)0.0484 (16)−0.0052 (11)−0.0098 (13)0.0133 (12)
C90.0311 (15)0.0283 (14)0.0589 (18)0.0046 (11)−0.0114 (13)−0.0017 (13)
C100.0254 (14)0.0392 (15)0.0483 (16)0.0031 (11)0.0012 (12)−0.0075 (13)
C110.0241 (13)0.0338 (13)0.0313 (13)−0.0005 (10)0.0035 (10)0.0013 (10)
C120.0279 (13)0.0285 (12)0.0220 (11)0.0041 (10)−0.0006 (10)0.0080 (9)
C130.0340 (14)0.0200 (11)0.0316 (12)0.0092 (10)0.0069 (11)0.0091 (9)
C140.0435 (15)0.0215 (12)0.0299 (13)0.0066 (11)0.0067 (11)0.0027 (10)
C150.0414 (15)0.0279 (13)0.0245 (12)0.0118 (11)0.0099 (11)0.0102 (10)
C160.0255 (12)0.0256 (12)0.0273 (12)0.0053 (9)0.0097 (10)0.0123 (9)
C170.0225 (12)0.0244 (11)0.0218 (11)−0.0016 (9)0.0035 (9)0.0056 (9)
C180.0188 (11)0.0231 (11)0.0223 (11)−0.0005 (9)0.0023 (9)0.0035 (9)
C190.0226 (12)0.0334 (13)0.0227 (11)0.0084 (10)0.0024 (9)0.0078 (10)
C200.0273 (13)0.0316 (13)0.0363 (13)0.0118 (10)0.0052 (11)0.0129 (11)
C210.0214 (12)0.0256 (12)0.0343 (13)0.0048 (9)0.0051 (10)0.0014 (10)
C220.0297 (13)0.0318 (13)0.0230 (12)−0.0008 (10)0.0051 (10)0.0014 (10)
C230.0320 (13)0.0264 (12)0.0241 (12)0.0014 (10)0.0031 (10)0.0063 (10)
C240.0279 (13)0.0281 (12)0.0287 (12)−0.0015 (10)−0.0056 (10)0.0102 (10)
Geometric parameters (Å, °) top
P1—F11.5843 (13)C5—H5B0.9900
P1—F51.5893 (13)C6—C71.386 (3)
P1—F41.5910 (14)C6—C111.395 (3)
P1—F21.5919 (14)C7—C81.389 (3)
P1—F31.6005 (13)C7—H70.9500
P1—F61.6035 (14)C8—C91.382 (4)
P2—F101.523 (6)C8—H80.9500
P2—F8'1.568 (4)C9—C101.384 (4)
P2—F111.569 (5)C9—H90.9500
P2—F71.572 (6)C10—C111.374 (3)
P2—F91.573 (6)C10—H100.9500
P2—F12'1.578 (5)C11—H110.9500
P2—F9'1.590 (4)C12—H12A0.9800
P2—F11'1.612 (4)C12—H12B0.9800
P2—F10'1.623 (4)C12—H12C0.9800
P2—F7'1.624 (4)C13—C141.517 (3)
P2—F81.624 (6)C13—H13A0.9900
P2—F121.626 (6)C13—H13B0.9900
O1—C31.425 (3)C14—H14A0.9900
O1—C21.427 (3)C14—H14B0.9900
O2—C151.424 (2)C15—C161.513 (3)
O2—C141.427 (3)C15—H15A0.9900
N1—C121.498 (3)C15—H15B0.9900
N1—C11.510 (2)C16—H16A0.9900
N1—C41.513 (3)C16—H16B0.9900
N1—C51.528 (3)C17—C181.512 (3)
N2—C241.503 (3)C17—H17A0.9900
N2—C161.509 (3)C17—H17B0.9900
N2—C131.515 (3)C18—C191.391 (3)
N2—C171.524 (3)C18—C231.391 (3)
C1—C21.512 (3)C19—C201.387 (3)
C1—H1A0.9900C19—H190.9500
C1—H1B0.9900C20—C211.383 (3)
C2—H2A0.9900C20—H200.9500
C2—H2B0.9900C21—C221.377 (3)
C3—C41.512 (3)C21—H210.9500
C3—H3A0.9900C22—C231.391 (3)
C3—H3B0.9900C22—H220.9500
C4—H4A0.9900C23—H230.9500
C4—H4B0.9900C24—H24A0.9800
C5—C61.503 (3)C24—H24B0.9800
C5—H5A0.9900C24—H24C0.9800
F1—P1—F590.51 (8)O1—C2—H2A109.4
F1—P1—F489.97 (8)C1—C2—H2A109.4
F5—P1—F490.45 (9)O1—C2—H2B109.4
F1—P1—F290.56 (8)C1—C2—H2B109.4
F5—P1—F289.86 (9)H2A—C2—H2B108.0
F4—P1—F2179.38 (8)O1—C3—C4111.43 (17)
F1—P1—F390.16 (7)O1—C3—H3A109.3
F5—P1—F3179.23 (8)C4—C3—H3A109.3
F4—P1—F389.18 (8)O1—C3—H3B109.3
F2—P1—F390.50 (8)C4—C3—H3B109.3
F1—P1—F6179.29 (8)H3A—C3—H3B108.0
F5—P1—F690.15 (8)C3—C4—N1112.51 (18)
F4—P1—F690.26 (8)C3—C4—H4A109.1
F2—P1—F689.20 (8)N1—C4—H4A109.1
F3—P1—F689.18 (7)C3—C4—H4B109.1
F10—P2—F8'157.7 (3)N1—C4—H4B109.1
F10—P2—F1194.0 (3)H4A—C4—H4B107.8
F8'—P2—F1164.7 (3)C6—C5—N1115.64 (17)
F10—P2—F793.1 (4)C6—C5—H5A108.4
F8'—P2—F781.6 (5)N1—C5—H5A108.4
F11—P2—F791.5 (4)C6—C5—H5B108.4
F10—P2—F992.6 (3)N1—C5—H5B108.4
F8'—P2—F9109.1 (3)H5A—C5—H5B107.4
F11—P2—F9172.8 (4)C7—C6—C11118.6 (2)
F7—P2—F991.0 (4)C7—C6—C5120.2 (2)
F10—P2—F12'92.7 (6)C11—C6—C5120.9 (2)
F8'—P2—F12'92.7 (3)C6—C7—C8120.9 (2)
F11—P2—F12'87.2 (5)C6—C7—H7119.6
F7—P2—F12'174.2 (6)C8—C7—H7119.6
F9—P2—F12'89.6 (6)C9—C8—C7119.7 (3)
F10—P2—F9'110.4 (3)C9—C8—H8120.1
F8'—P2—F9'91.0 (2)C7—C8—H8120.1
F11—P2—F9'155.6 (3)C8—C9—C10119.7 (2)
F7—P2—F9'86.9 (6)C8—C9—H9120.1
F9—P2—F9'18.2 (3)C10—C9—H9120.1
F12'—P2—F9'91.9 (3)C11—C10—C9120.5 (2)
F10—P2—F11'67.6 (3)C11—C10—H10119.7
F8'—P2—F11'90.77 (19)C9—C10—H10119.7
F11—P2—F11'26.5 (3)C10—C11—C6120.5 (2)
F7—P2—F11'90.7 (5)C10—C11—H11119.7
F9—P2—F11'160.1 (3)C6—C11—H11119.7
F12'—P2—F11'90.7 (3)N1—C12—H12A109.5
F9'—P2—F11'176.8 (3)N1—C12—H12B109.5
F10—P2—F10'21.1 (4)H12A—C12—H12B109.5
F8'—P2—F10'177.2 (3)N1—C12—H12C109.5
F11—P2—F10'114.7 (3)H12A—C12—H12C109.5
F7—P2—F10'95.7 (6)H12B—C12—H12C109.5
F9—P2—F10'71.7 (3)N2—C13—C14111.92 (17)
F12'—P2—F10'90.0 (3)N2—C13—H13A109.2
F9'—P2—F10'89.7 (2)C14—C13—H13A109.2
F11'—P2—F10'88.5 (2)N2—C13—H13B109.2
F10—P2—F7'84.8 (6)C14—C13—H13B109.2
F8'—P2—F7'89.7 (3)H13A—C13—H13B107.9
F11—P2—F7'93.0 (5)O2—C14—C13111.06 (19)
F7—P2—F7'8.3 (7)O2—C14—H14A109.4
F9—P2—F7'90.4 (6)C13—C14—H14A109.4
F12'—P2—F7'177.5 (4)O2—C14—H14B109.4
F9'—P2—F7'88.9 (3)C13—C14—H14B109.4
F11'—P2—F7'88.4 (3)H14A—C14—H14B108.0
F10'—P2—F7'87.6 (3)O2—C15—C16111.24 (17)
F10—P2—F8177.2 (4)O2—C15—H15A109.4
F8'—P2—F823.8 (2)C16—C15—H15A109.4
F11—P2—F886.7 (3)O2—C15—H15B109.4
F7—P2—F889.6 (4)C16—C15—H15B109.4
F9—P2—F886.6 (3)H15A—C15—H15B108.0
F12'—P2—F884.6 (5)N2—C16—C15111.46 (18)
F9'—P2—F868.9 (3)N2—C16—H16A109.3
F11'—P2—F8113.2 (2)C15—C16—H16A109.3
F10'—P2—F8157.7 (2)N2—C16—H16B109.3
F7'—P2—F897.9 (5)C15—C16—H16B109.3
F10—P2—F1290.5 (4)H16A—C16—H16B108.0
F8'—P2—F1295.1 (5)C18—C17—N2116.30 (17)
F11—P2—F1288.5 (4)C18—C17—H17A108.2
F7—P2—F12176.4 (5)N2—C17—H17A108.2
F9—P2—F1288.6 (4)C18—C17—H17B108.2
F12'—P2—F122.4 (7)N2—C17—H17B108.2
F9'—P2—F1291.7 (6)H17A—C17—H17B107.4
F11'—P2—F1290.9 (5)C19—C18—C23118.67 (19)
F10'—P2—F1287.6 (6)C19—C18—C17121.67 (19)
F7'—P2—F12175.2 (6)C23—C18—C17119.42 (19)
F8—P2—F1286.8 (4)C20—C19—C18120.6 (2)
C3—O1—C2110.05 (17)C20—C19—H19119.7
C15—O2—C14110.09 (15)C18—C19—H19119.7
C12—N1—C1111.17 (16)C21—C20—C19120.1 (2)
C12—N1—C4111.53 (16)C21—C20—H20119.9
C1—N1—C4107.61 (16)C19—C20—H20119.9
C12—N1—C5109.33 (16)C22—C21—C20119.8 (2)
C1—N1—C5110.28 (15)C22—C21—H21120.1
C4—N1—C5106.81 (16)C20—C21—H21120.1
C24—N2—C16108.23 (17)C21—C22—C23120.2 (2)
C24—N2—C13109.28 (16)C21—C22—H22119.9
C16—N2—C13107.35 (15)C23—C22—H22119.9
C24—N2—C17109.83 (16)C22—C23—C18120.5 (2)
C16—N2—C17113.36 (16)C22—C23—H23119.8
C13—N2—C17108.70 (16)C18—C23—H23119.8
N1—C1—C2112.04 (16)N2—C24—H24A109.5
N1—C1—H1A109.2N2—C24—H24B109.5
C2—C1—H1A109.2H24A—C24—H24B109.5
N1—C1—H1B109.2N2—C24—H24C109.5
C2—C1—H1B109.2H24A—C24—H24C109.5
H1A—C1—H1B107.9H24B—C24—H24C109.5
O1—C2—C1110.99 (18)
C12—N1—C1—C2−70.4 (2)C24—N2—C13—C14170.01 (18)
C4—N1—C1—C252.0 (2)C16—N2—C13—C1452.8 (2)
C5—N1—C1—C2168.14 (17)C17—N2—C13—C14−70.1 (2)
C3—O1—C2—C161.1 (2)C15—O2—C14—C1360.1 (2)
N1—C1—C2—O1−58.5 (2)N2—C13—C14—O2−57.5 (2)
C2—O1—C3—C4−60.1 (2)C14—O2—C15—C16−61.0 (2)
O1—C3—C4—N156.6 (2)C24—N2—C16—C15−171.17 (16)
C12—N1—C4—C371.1 (2)C13—N2—C16—C15−53.3 (2)
C1—N1—C4—C3−51.1 (2)C17—N2—C16—C1566.7 (2)
C5—N1—C4—C3−169.51 (17)O2—C15—C16—N259.0 (2)
C12—N1—C5—C6−56.4 (2)C24—N2—C17—C18−57.3 (2)
C1—N1—C5—C666.1 (2)C16—N2—C17—C1863.9 (2)
C4—N1—C5—C6−177.22 (17)C13—N2—C17—C18−176.85 (17)
N1—C5—C6—C7101.2 (2)N2—C17—C18—C19−80.6 (2)
N1—C5—C6—C11−84.4 (2)N2—C17—C18—C23105.1 (2)
C11—C6—C7—C80.2 (3)C23—C18—C19—C20−1.9 (3)
C5—C6—C7—C8174.8 (2)C17—C18—C19—C20−176.3 (2)
C6—C7—C8—C90.0 (4)C18—C19—C20—C212.5 (3)
C7—C8—C9—C100.2 (4)C19—C20—C21—C22−1.1 (3)
C8—C9—C10—C11−0.6 (4)C20—C21—C22—C23−0.9 (3)
C9—C10—C11—C60.8 (4)C21—C22—C23—C181.5 (3)
C7—C6—C11—C10−0.6 (3)C19—C18—C23—C22−0.1 (3)
C5—C6—C11—C10−175.1 (2)C17—C18—C23—C22174.43 (19)
Acknowledgements top

The authors thank the Tianjin Natural Science Foundation (07JCYBJC02200) and (10JCZDJC22200) for financial support.

references
References top

Kim, K. S., Choi, S., Cha, J. H., Yeon, S. H. & Lee, H. (2006). J. Mater. Chem. 16, 1315–1317.

Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.