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Acta Cryst. (2007). E63, o3075
https://doi.org/10.1107/S1600536807026232
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The protonated β-imino­amine 1,3-bis­(2-methyl­anilino)-1-phenyl­butane­(1+) hexa­fluoro­phosphate

N. B. M. Elmkacher, M. Rzaigui and F. Bouachir
The title compound, C24H25N2+·PF6−, is a bis­(imininium) hexa­fluoro­phosphate salt with inter­ionic inter­actions. Significant delocalization within the π-system of the N—C—C—C—N backbone is suggested.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026232/av3093sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026232/av3093Isup2.hkl
Contains datablock I

CCDC reference: 654860

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.051
  • wR factor = 0.145
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.
PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         11


Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       0.30
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.00
PLAT128_ALERT_4_C Non-standard setting of Space group Pca21   ....    Pc21b
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2


Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           24.97
           From the CIF: _reflns_number_total               2170
           Count of symmetry unique reflns         2172
           Completeness (_total/calc)             99.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1


   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Recent years have witnessed an impressive revival of interest in bidentate β-diketiminate ligands, which have been known for more than four decades (Holm & O'Connor, 1971). β-Diketiminates are important spectator ligands by virtue of their strong binding to metals, their tunable and extensive steric demands, and their diversity of bonding modes (Bourget-Merle et al., 2002). For example, their steric and electronic properties can be readily tuned by an appropriate choice of starting materials used in their synthesis. They can form a conjugated π-system due to essential electron delocalization along the ligand. Recently, we have been interested in the synthesis of the new nonsymmetrical β-iminoamines and their coordination in their neutral form as β-diimine nickel complexes (Landolsi et al., 2002).

The crystal structure is composed of a cation (β-iminoamineH) and hexafluorophosphate anion with interionic interaction. The shortest F—C distance is F2—C13 [3.551 Å]. The hexafluorophosphate anion possesses an octahedral geometry, with P—F distances ranging from 1.523 to 1.585 Å. The cation adopts an open configuration with intramolecular interaction. The distance H2—N2 (2.366 Å) and H2—N1 (2.487 Å) are shorter than the sum of their van der Waals radii. The N—C [N1—C1 1.317 and N2—C3 1.340 Å] and the C—C [C2—C3 1.387 and C2—C1 1.388 Å] bond distances lie intermediate between the corresponding single and double-bond distances, which suggest significant delocalization within the π-system of the N—C—C—C—N backbone (Allen et al., 1992). The methyl and phenyl groups of the backbone adopt a syn orientation; the two aryl rings adopt a synperiplanar arrangement in order to minimize steric crowding.

Related literature top

Recent years have witnessed an impressive revival of interest in bidentate β-diketiminate ligands, which have been known for more than four decades (Holm & O'Connor, 1971). β-Diketiminates are important spectator ligands by virtue of their strong binding to metals, their tunable and extensive steric demands, and their diversity of bonding modes (Bourget-Merle et al., 2002). For example, their steric and electronic properties can be readily tuned by an appropriate choice of starting materials used in their synthesis. They can form a conjugated π-system due to essential electron delocalization along the ligand. Recently, we have been interested in the synthesis of the new nonsymmetrical β-iminoamines and their coordination in their neutral form as β-diimine nickel complexes (Landolsi et al., 2002).

For related literature, see: Allen et al. (1992).

Experimental top

Compound (I) was obtained after recristallization of the cationic methallyl β-diimine Nickel complexes in methylene chloride with traces of acid. In fact the β-diimine precursors were synthesized by acid-catalysed condensation of benzoylacteone and 2-methylaniline in toluene using a Dean Stark apparatus. Crystals were obtained from a diluted solution in methylene chloride /n-hexane at 243 K.

Refinement top

Hydrogen atoms H2, HN1 and HN2 were located in a Fourier map and refined freely. All the other H atoms were placed in calculated positions and allowed to ride on their parent atoms. Uiso of H atoms are equal to 1.2 Uiso of the parent atom. We chose the non standard space group because when we chose the standard space group, we found problems in the structure resolution.

Structure description top

Recent years have witnessed an impressive revival of interest in bidentate β-diketiminate ligands, which have been known for more than four decades (Holm & O'Connor, 1971). β-Diketiminates are important spectator ligands by virtue of their strong binding to metals, their tunable and extensive steric demands, and their diversity of bonding modes (Bourget-Merle et al., 2002). For example, their steric and electronic properties can be readily tuned by an appropriate choice of starting materials used in their synthesis. They can form a conjugated π-system due to essential electron delocalization along the ligand. Recently, we have been interested in the synthesis of the new nonsymmetrical β-iminoamines and their coordination in their neutral form as β-diimine nickel complexes (Landolsi et al., 2002).

The crystal structure is composed of a cation (β-iminoamineH) and hexafluorophosphate anion with interionic interaction. The shortest F—C distance is F2—C13 [3.551 Å]. The hexafluorophosphate anion possesses an octahedral geometry, with P—F distances ranging from 1.523 to 1.585 Å. The cation adopts an open configuration with intramolecular interaction. The distance H2—N2 (2.366 Å) and H2—N1 (2.487 Å) are shorter than the sum of their van der Waals radii. The N—C [N1—C1 1.317 and N2—C3 1.340 Å] and the C—C [C2—C3 1.387 and C2—C1 1.388 Å] bond distances lie intermediate between the corresponding single and double-bond distances, which suggest significant delocalization within the π-system of the N—C—C—C—N backbone (Allen et al., 1992). The methyl and phenyl groups of the backbone adopt a syn orientation; the two aryl rings adopt a synperiplanar arrangement in order to minimize steric crowding.

Recent years have witnessed an impressive revival of interest in bidentate β-diketiminate ligands, which have been known for more than four decades (Holm & O'Connor, 1971). β-Diketiminates are important spectator ligands by virtue of their strong binding to metals, their tunable and extensive steric demands, and their diversity of bonding modes (Bourget-Merle et al., 2002). For example, their steric and electronic properties can be readily tuned by an appropriate choice of starting materials used in their synthesis. They can form a conjugated π-system due to essential electron delocalization along the ligand. Recently, we have been interested in the synthesis of the new nonsymmetrical β-iminoamines and their coordination in their neutral form as β-diimine nickel complexes (Landolsi et al., 2002).

For related literature, see: Allen et al. (1992).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.
1,3-bis(2-methylanilino)-1-phenylbutane(1+) hexafluorophosphate top
Crystal data top
C24H25N2+·F6P−F(000) = 1008
Mr = 486.43Dx = 1.355 Mg m−3
Orthorhombic, Pc21bMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2bc -2cCell parameters from 0 reflections
a = 6.5352 (2) Åθ = 0–0°
b = 17.8580 (3) ŵ = 0.18 mm−1
c = 20.4249 (3) ÅT = 293 K
V = 2383.70 (9) Å3Prism, colourless
Z = 40.35 × 0.23 × 0.23 mm
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer		Rint = 0.069
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = −7→7
non–profiled ω scansk = 0→21
4127 measured reflectionsl = 0→24
2170 independent reflections2 standard reflections every 120 min
1221 reflections with I > 2σ(I) intensity decay: −2%
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)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.073P)2 + 0.2103P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.026
2170 reflectionsΔρmax = 0.24 e Å−3
310 parametersΔρmin = −0.23 e Å−3
1 restraintAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (3)
Crystal data top
C24H25N2+·F6P−V = 2383.70 (9) Å3
Mr = 486.43Z = 4
Orthorhombic, Pc21bMo Kα radiation
a = 6.5352 (2) ŵ = 0.18 mm−1
b = 17.8580 (3) ÅT = 293 K
c = 20.4249 (3) Å0.35 × 0.23 × 0.23 mm
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer		Rint = 0.069
4127 measured reflections2 standard reflections every 120 min
2170 independent reflections intensity decay: −2%
1221 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145Δρmax = 0.24 e Å−3
S = 1.01Δρmin = −0.23 e Å−3
2170 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
310 parametersAbsolute structure parameter: 0.1 (3)
1 restraint
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*/Ueq
P10.4127 (3)1.09449 (11)0.65597 (9)0.0592 (5)
F10.1705 (6)1.0943 (4)0.6594 (3)0.122 (2)
F20.4234 (8)1.0619 (4)0.7256 (2)0.116 (2)
F30.6520 (7)1.0964 (4)0.6521 (3)0.130 (2)
F40.4089 (11)1.0144 (3)0.6304 (3)0.145 (3)
F50.4123 (12)1.1747 (3)0.6844 (5)0.183 (4)
F60.3998 (11)1.1268 (6)0.5861 (3)0.201 (4)
N10.9600 (9)0.7527 (3)0.8552 (3)0.0527 (15)
HN11.017 (11)0.710 (4)0.846 (3)0.063*
N20.7305 (8)0.9378 (3)0.9982 (3)0.0537 (15)
HN20.690 (10)0.954 (4)1.037 (4)0.064*
C10.8882 (10)0.7642 (3)0.9146 (3)0.0460 (15)
C20.8214 (10)0.8358 (3)0.9301 (3)0.0471 (16)
H20.835 (10)0.872 (4)0.903 (3)0.057*
C30.7419 (10)0.8638 (4)0.9881 (3)0.0531 (17)
C40.9014 (12)0.6988 (4)0.9598 (3)0.0604 (19)
H4A0.77560.67110.95820.073*
H4B0.92460.71621.00370.073*
H4C1.01250.66700.94670.073*
C50.6616 (10)0.8156 (4)1.0419 (3)0.0518 (17)
C60.7487 (12)0.8162 (5)1.1027 (3)0.070 (2)
H60.85400.84951.11200.084*
C70.6804 (15)0.7672 (5)1.1508 (3)0.085 (3)
H70.74300.76671.19170.102*
C80.5230 (14)0.7200 (5)1.1382 (4)0.077 (2)
H80.47650.68761.17060.092*
C90.4328 (12)0.7202 (5)1.0780 (4)0.076 (2)
H90.32470.68781.06960.091*
C100.4996 (12)0.7680 (4)1.0291 (3)0.067 (2)
H100.43650.76810.98830.081*
C110.8208 (11)0.9904 (4)0.9537 (3)0.0568 (18)
C120.7082 (13)1.0115 (4)0.8981 (4)0.069 (2)
H120.57370.99550.89290.084*
C130.7985 (17)1.0559 (4)0.8513 (4)0.079 (2)
H130.72661.06900.81370.095*
C140.9954 (18)1.0810 (5)0.8603 (5)0.084 (3)
H141.05541.11140.82870.101*
C151.1061 (14)1.0614 (4)0.9158 (5)0.079 (2)
H151.23831.07950.92160.095*
C161.0175 (12)1.0140 (4)0.9632 (3)0.0581 (18)
C171.1384 (14)0.9891 (5)1.0219 (4)0.088 (3)
H17A1.06311.00031.06110.106*
H17B1.26721.01491.02280.106*
H17C1.16220.93611.01930.106*
C180.9586 (11)0.8083 (3)0.8044 (3)0.0502 (17)
C190.7921 (12)0.8119 (5)0.7617 (4)0.067 (2)
H190.69130.77520.76330.080*
C200.7763 (15)0.8686 (6)0.7179 (4)0.088 (3)
H200.66370.87200.69030.106*
C210.9319 (17)0.9217 (5)0.7152 (4)0.085 (3)
H210.92360.96070.68520.102*
C221.0939 (15)0.9173 (4)0.7556 (4)0.074 (2)
H221.19560.95360.75250.088*
C231.1152 (12)0.8606 (4)0.8017 (3)0.0617 (19)
C241.2965 (12)0.8572 (5)0.8484 (4)0.089 (3)
H24A1.41630.87610.82680.106*
H24B1.31950.80620.86130.106*
H24C1.26790.88700.88640.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C240.063 (5)0.078 (6)0.125 (8)−0.021 (4)0.007 (5)−0.029 (6)
P10.0545 (11)0.0530 (10)0.0701 (12)−0.0028 (12)−0.0011 (10)0.0105 (10)
F10.057 (3)0.132 (4)0.176 (5)0.000 (4)−0.009 (3)0.062 (4)
N10.066 (4)0.033 (3)0.059 (4)0.001 (3)0.006 (3)0.000 (3)
C30.050 (4)0.052 (4)0.057 (4)−0.008 (3)−0.003 (3)−0.011 (4)
C40.079 (5)0.046 (4)0.057 (4)0.005 (4)0.002 (4)0.002 (3)
N20.058 (4)0.043 (3)0.060 (3)−0.009 (3)0.013 (3)−0.016 (3)
C230.073 (5)0.051 (4)0.061 (4)−0.006 (4)0.022 (4)−0.016 (4)
C90.069 (5)0.079 (5)0.079 (6)−0.021 (5)0.006 (4)0.011 (5)
C10.049 (4)0.043 (4)0.046 (4)−0.007 (3)0.005 (3)−0.004 (3)
F20.103 (4)0.164 (6)0.080 (3)−0.022 (4)−0.016 (3)0.041 (3)
F30.058 (3)0.158 (5)0.175 (5)−0.005 (4)0.012 (3)0.058 (5)
C150.080 (5)0.060 (5)0.098 (6)−0.014 (5)0.026 (5)−0.013 (5)
C160.062 (5)0.048 (4)0.064 (4)−0.007 (4)0.003 (4)−0.011 (3)
C60.090 (6)0.068 (5)0.052 (4)−0.016 (5)−0.004 (4)−0.009 (4)
C100.074 (5)0.071 (5)0.056 (4)−0.016 (5)0.000 (4)0.011 (4)
C130.122 (8)0.052 (4)0.063 (5)0.011 (5)−0.008 (5)0.001 (4)
C210.130 (9)0.071 (6)0.054 (5)0.010 (6)0.030 (6)0.016 (4)
C80.108 (7)0.072 (5)0.051 (5)−0.015 (5)0.020 (4)−0.003 (4)
F40.166 (7)0.095 (4)0.175 (6)0.007 (4)−0.019 (5)−0.051 (4)
C190.073 (5)0.072 (5)0.055 (5)−0.007 (4)0.001 (4)0.000 (4)
C140.121 (7)0.060 (6)0.071 (6)0.000 (6)0.026 (5)−0.001 (4)
C180.061 (5)0.045 (4)0.044 (4)−0.001 (3)0.019 (3)−0.008 (3)
C200.092 (7)0.109 (7)0.064 (5)0.007 (6)−0.004 (5)0.018 (5)
C20.061 (4)0.037 (3)0.043 (4)−0.003 (3)0.015 (3)−0.001 (3)
C220.098 (6)0.057 (5)0.065 (5)−0.017 (5)0.032 (5)−0.004 (4)
C50.056 (4)0.051 (4)0.049 (4)−0.010 (3)0.009 (3)−0.008 (3)
C120.076 (5)0.050 (4)0.082 (5)0.008 (4)0.000 (4)−0.018 (4)
C110.068 (5)0.041 (4)0.062 (4)0.002 (4)−0.001 (4)−0.012 (4)
C170.078 (6)0.085 (6)0.100 (7)−0.012 (5)−0.012 (5)−0.009 (5)
C70.127 (8)0.084 (6)0.043 (4)−0.004 (6)−0.012 (5)−0.017 (5)
F50.178 (8)0.073 (4)0.299 (10)−0.005 (5)−0.020 (7)−0.062 (6)
F60.132 (5)0.342 (13)0.129 (5)−0.037 (7)−0.016 (4)0.148 (7)
Geometric parameters (Å, º) top
C24—C231.522 (11)C15—H150.9300
C24—H24A0.9600C16—C111.367 (10)
C24—H24B0.9600C16—C171.504 (10)
C24—H24C0.9600C6—C51.367 (9)
P1—F41.523 (6)C6—C71.389 (11)
P1—F21.539 (5)C6—H60.9300
P1—F61.541 (6)C10—C51.382 (9)
P1—F51.547 (6)C10—H100.9300
P1—F31.566 (5)C13—C141.374 (12)
P1—F11.585 (5)C13—C121.375 (11)
N1—C11.317 (8)C13—H130.9300
N1—C181.436 (8)C21—C221.344 (11)
N1—HN10.87 (7)C21—C201.391 (13)
C3—N21.340 (9)C21—H210.9300
C3—C21.387 (9)C8—C71.354 (12)
C3—C51.492 (9)C8—H80.9300
C4—C11.491 (8)C19—C201.354 (11)
C4—H4A0.9600C19—C181.396 (10)
C4—H4B0.9600C19—H190.9300
C4—H4C0.9600C14—H140.9300
N2—C111.434 (9)C20—H200.9300
N2—HN20.88 (7)C2—H20.86 (7)
C23—C181.387 (9)C22—H220.9300
C23—C221.390 (10)C12—C111.404 (10)
C9—C81.364 (10)C12—H120.9300
C9—C101.384 (9)C17—H17A0.9600
C9—H90.9300C17—H17B0.9600
C1—C21.388 (9)C17—H17C0.9600
C15—C141.389 (13)C7—H70.9300
C15—C161.410 (10)
C23—C24—H24A109.5C5—C6—C7120.2 (7)
C23—C24—H24B109.5C5—C6—H6119.9
H24A—C24—H24B109.5C7—C6—H6119.9
C23—C24—H24C109.5C5—C10—C9118.9 (7)
H24A—C24—H24C109.5C5—C10—H10120.5
H24B—C24—H24C109.5C9—C10—H10120.5
F4—P1—F287.9 (4)C14—C13—C12119.8 (8)
F4—P1—F691.9 (6)C14—C13—H13120.1
F2—P1—F6179.4 (4)C12—C13—H13120.1
F4—P1—F5177.7 (5)C22—C21—C20120.8 (8)
F2—P1—F590.2 (5)C22—C21—H21119.6
F6—P1—F590.1 (6)C20—C21—H21119.6
F4—P1—F391.1 (4)C7—C8—C9119.8 (7)
F2—P1—F390.5 (3)C7—C8—H8120.1
F6—P1—F390.0 (4)C9—C8—H8120.1
F5—P1—F390.0 (5)C20—C19—C18120.4 (8)
F4—P1—F189.8 (4)C20—C19—H19119.8
F2—P1—F190.2 (3)C18—C19—H19119.8
F6—P1—F189.2 (4)C13—C14—C15121.0 (8)
F5—P1—F189.1 (4)C13—C14—H14119.5
F3—P1—F1178.8 (4)C15—C14—H14119.5
C1—N1—C18123.8 (6)C23—C18—N1119.3 (7)
C1—N1—HN1120 (5)C19—C18—N1119.3 (6)
C18—N1—HN1116 (5)C19—C20—C21118.7 (9)
N2—C3—C2120.5 (6)C19—C20—H20120.6
N2—C3—C5115.9 (6)C21—C20—H20120.7
C2—C3—C5123.5 (6)C3—C2—C1130.2 (6)
C1—C4—H4A109.5C3—C2—H2108 (5)
C1—C4—H4B109.5C1—C2—H2121 (5)
H4A—C4—H4B109.5C21—C22—C23122.5 (8)
C1—C4—H4C109.5C21—C22—H22118.8
H4A—C4—H4C109.5C23—C22—H22118.8
H4B—C4—H4C109.5C6—C5—C10119.7 (7)
C3—N2—C11121.7 (5)C6—C5—C3121.2 (6)
C3—N2—HN2118 (5)C10—C5—C3119.0 (6)
C11—N2—HN2119 (5)C13—C12—C11119.4 (8)
C18—C23—C22116.4 (8)C13—C12—H12120.3
C18—C23—C24121.5 (7)C11—C12—H12120.3
C22—C23—C24122.1 (7)C16—C11—C12121.7 (7)
C8—C9—C10121.1 (8)C16—C11—N2119.9 (7)
C8—C9—H9119.5C12—C11—N2118.2 (7)
C10—C9—H9119.5C16—C17—H17A109.5
N1—C1—C2117.8 (6)C16—C17—H17B109.5
N1—C1—C4115.4 (6)H17A—C17—H17B109.5
C2—C1—C4126.8 (6)C16—C17—H17C109.5
C14—C15—C16119.8 (8)H17A—C17—H17C109.5
C14—C15—H15120.1H17B—C17—H17C109.5
C16—C15—H15120.1C8—C7—C6120.1 (7)
C11—C16—C15118.3 (7)C8—C7—H7119.9
C11—C16—C17121.0 (7)C6—C7—H7119.9
C15—C16—C17120.6 (8)

Experimental details

Crystal data
Chemical formulaC24H25N2+·F6P−
Mr486.43
Crystal system, space groupOrthorhombic, Pc21b
Temperature (K)293
a, b, c (Å)6.5352 (2), 17.8580 (3), 20.4249 (3)
V (Å3)2383.70 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.18
Crystal size (mm)0.35 × 0.23 × 0.23
Data collection
DiffractometerEnraf–Nonius TurboCAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		4127, 2170, 1221
Rint0.069
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.145, 1.01
No. of reflections2170
No. of parameters310
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.23
Absolute structureFlack (1983), with how many Friedel pairs?
Absolute structure parameter0.1 (3)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
N1—C11.317 (8)C3—C51.492 (9)
N1—C181.436 (8)C4—C11.491 (8)
C3—N21.340 (9)N2—C111.434 (9)
C3—C21.387 (9)C1—C21.388 (9)
C1—N1—C18123.8 (6)N1—C1—C2117.8 (6)
N2—C3—C2120.5 (6)N1—C1—C4115.4 (6)
N2—C3—C5115.9 (6)C3—C2—C1130.2 (6)
C3—N2—C11121.7 (5)
 

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