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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

Di­cyclo­hexyl­bis­­(naphthalen-1-ylmeth­yl)phospho­nium chloride chloro­form disolvate

aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: matthias.beller@catalysis.de

(Received 26 October 2012; accepted 12 November 2012; online 17 November 2012)

In the title solvated phosphonium salt, C34H40P+·Cl·2CHCl3, the two cyclo­hexyl and two 1-naphthyl­methyl groups at the P atom are in a distorted tetra­hedral arrangement [105.26 (6)–113.35 (6)°]. Both cyclo­hexyl rings adopt a chair conformation. The dihedral angle between the naphthyl ring systems is 74.08 (3)°.

Related literature

A multitude of phospho­nium salts are known in the literature. For some examples of the type [PR2R′′2]X (R′ = Me, R′′ = Ph, X = I), see: Staples et al. (1995[Staples, R. J., Carlson, T., Wang, S. & Fackler, J. P. (1995). Acta Cryst. C51, 498-500.]); Dornhaus et al. (2005[Dornhaus, F., Lerner, H.-W. & Bolte, M. (2005). Acta Cryst. E61, o1657-o1658.]), (R′ = Me, R′′ = Ph, X = Br), see: Staples et al. (1995[Staples, R. J., Carlson, T., Wang, S. & Fackler, J. P. (1995). Acta Cryst. C51, 498-500.]) and (R′ = Me, R′′ = fluoren-9-yl, X = I), see: Brady et al. (2000[Brady, E. D., Hanusa, T. P., Pink, M. & Young, V. G. Jr (2000). Inorg. Chem. 39, 6028-6037.]).

[Scheme 1]

Experimental

Crystal data
  • C34H40P+·Cl·2CHCl3

  • Mr = 753.82

  • Triclinic, [P \overline 1]

  • a = 12.3079 (2) Å

  • b = 12.7150 (2) Å

  • c = 14.0310 (3) Å

  • α = 77.785 (1)°

  • β = 64.242 (1)°

  • γ = 64.738 (1)°

  • V = 1787.56 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.63 mm−1

  • T = 150 K

  • 0.43 × 0.30 × 0.19 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.96, Tmax = 1.00

  • 40097 measured reflections

  • 8871 independent reflections

  • 7562 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.080

  • S = 1.03

  • 8871 reflections

  • 397 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Phosphonium salts are used in a wide range of applications such as ionic liquids, as antimicrobial agents, and as surfactants. Recently, we were interested in the preparation of dicyclohexyl(1-naphthylmethyl)phosphine. During this preparation, dicyclohexylbis(1-naphthylmethyl)phosphonium chloride was formed in a rapid and highly selective manner. We have now observed a reaction of 1-(chloromethyl)naphthalene with Cy2PH at 50 °C in acetone which produces the phosphonium salt in nearly quantitative yield. Interestingly, this phosphonium salt is unknown in the literature. Crystals suitable for X-ray crystal structure analysis could be obtained by crystallization from a chloroform/heptane mixture.

The asymmetric unit of the title compound contains besides one unit of the phosphonium chloride, two chloroform molecules (Fig. 1). The phosphorus atom carries two cyclohexyl and two 1-naphthylmethyl groups. Its tetrahedral environment is expressed by C–P–C angles of 105.26 (6) — 113.35 (6)° (Fig. 2). The dihedral angle between the naphthyl groups is 74.08 (3)°. Both cyclohexyl rings adopt the chair conformation.

Related literature top

A multitude of phosphonium salts are known in the literature. For some examples of the type [PR'2R''2]X (R' = Me, R'' = Ph, X = I), see: Staples et al. (1995); Dornhaus et al. (2005), (R' = Me, R'' = Ph, X = Br), see: Staples et al. (1995) and (R' = Me, R'' = fluoren-9-yl, X = I), see: Brady et al. (2000).

Experimental top

1-(chloromethyl)naphthalene (4.50 mmol, 795 mg) and dicyclohexylphosphine (2.25 mmol, 500 mg) were dissolved in 4 ml of anhydrous acetone. The solution was stirred at 40 °C overnight. Afterwards acetone was removed in vacuo, the residue was dissolved in water and extracted with 50 ml of CHCl3. After concentration, 1100 mg (95%) of the title compound were obtained. Colourless crystals suitable for X-ray analysis, were grown from a CHCl3/heptane mixture at 8 °C for 4 days. 1H NMR (CDCl3, internal TMS): δ 8.39–8.36 (m, 1H), 7.83–7.72 (m, 2H), 7.69–7.64 (m, 1H), 7.61–7.53 (m, 1H), 7.49–7.41 (m, 1H), 7.40–7.32 (m, 1H), 4.85 (d, J = 15.0 Hz, 2H), 2.77–2.58 (m, 1H), 1.61–1.44 (m, 4H), 1.22–0.75 (m, 6H). 31P NMR (CDCl3, internal TMS): 32.35. HRMS: calcd. for C34H40P+: 479.28621; found: 479.28541.

Refinement top

H atoms were placed in idealized positions with d(C—H) = 0.95 Å (Caromatic—H), 1.00 Å (Ctertiary—H), 0.99 Å (CH2) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with 30% displacement ellipsoids. Hydrogen atoms are omitted for clarity. The asymmetric unit contains besides one molecule of the phosphonium chloride two chloroform solvent molecules.
[Figure 2] Fig. 2. Displacement ellipsoid plot (30%) of the cation [C34H40P]+ with hydrogen atoms depicted as small arbitrary circles.
Dicyclohexylbis(naphthalen-1-ylmethyl)phosphonium chloride chloroform disolvate top
Crystal data top
C34H40P+·Cl·2CHCl3Z = 2
Mr = 753.82F(000) = 784
Triclinic, P1Dx = 1.401 Mg m3
a = 12.3079 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.7150 (2) ÅCell parameters from 9914 reflections
c = 14.0310 (3) Åθ = 2.4–28.8°
α = 77.785 (1)°µ = 0.63 mm1
β = 64.242 (1)°T = 150 K
γ = 64.738 (1)°Prism, colourless
V = 1787.56 (6) Å30.43 × 0.30 × 0.19 mm
Data collection top
Bruker Kappa APEXII DUO
diffractometer
8871 independent reflections
Radiation source: fine-focus sealed tube7562 reflections with I > 2σ(I)
Curved graphite monochromatorRint = 0.025
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 1.6°
ω and ϕ scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 1616
Tmin = 0.96, Tmax = 1.00l = 1818
40097 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0389P)2 + 0.7399P]
where P = (Fo2 + 2Fc2)/3
8871 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C34H40P+·Cl·2CHCl3γ = 64.738 (1)°
Mr = 753.82V = 1787.56 (6) Å3
Triclinic, P1Z = 2
a = 12.3079 (2) ÅMo Kα radiation
b = 12.7150 (2) ŵ = 0.63 mm1
c = 14.0310 (3) ÅT = 150 K
α = 77.785 (1)°0.43 × 0.30 × 0.19 mm
β = 64.242 (1)°
Data collection top
Bruker Kappa APEXII DUO
diffractometer
8871 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
7562 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 1.00Rint = 0.025
40097 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.03Δρmax = 0.53 e Å3
8871 reflectionsΔρmin = 0.44 e Å3
397 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
xyzUiso*/Ueq
C10.44144 (12)0.61109 (11)0.90253 (10)0.0165 (2)
H1A0.51590.53750.87450.020*
H1B0.41730.60980.97980.020*
C20.32732 (12)0.61845 (11)0.88257 (10)0.0167 (2)
C30.20342 (12)0.68760 (12)0.94598 (10)0.0197 (2)
H30.19050.71821.00790.024*
C40.09523 (13)0.71393 (12)0.92063 (11)0.0230 (3)
H40.01070.76270.96480.028*
C50.11233 (13)0.66932 (12)0.83288 (11)0.0225 (3)
H50.04020.69100.81380.027*
C60.23635 (12)0.59097 (11)0.76938 (10)0.0186 (2)
C70.25333 (14)0.54077 (12)0.68056 (11)0.0236 (3)
H70.18040.55930.66340.028*
C80.37273 (14)0.46629 (13)0.61920 (11)0.0260 (3)
H80.38290.43440.55900.031*
C90.48129 (14)0.43644 (12)0.64492 (11)0.0250 (3)
H90.56390.38300.60280.030*
C100.46889 (13)0.48361 (11)0.72995 (10)0.0204 (2)
H100.54310.46290.74600.024*
C110.34605 (12)0.56336 (11)0.79468 (10)0.0170 (2)
C120.36962 (12)0.85580 (11)0.92346 (10)0.0202 (2)
H12A0.28260.85740.93820.024*
H12B0.37970.84090.99190.024*
C130.37027 (12)0.97536 (11)0.88234 (10)0.0189 (2)
C140.46891 (13)1.00426 (12)0.87525 (11)0.0237 (3)
H140.53700.94780.89530.028*
C150.47188 (15)1.11567 (13)0.83897 (12)0.0299 (3)
H150.54141.13350.83470.036*
C160.37468 (15)1.19780 (13)0.80997 (12)0.0297 (3)
H160.37781.27220.78430.036*
C170.26942 (14)1.17314 (12)0.81783 (10)0.0242 (3)
C180.16649 (17)1.25885 (13)0.78941 (12)0.0339 (4)
H180.17021.33290.76270.041*
C190.06345 (16)1.23673 (14)0.79980 (13)0.0361 (4)
H190.00401.29500.78000.043*
C200.05607 (15)1.12812 (14)0.83962 (13)0.0320 (3)
H200.01731.11370.84800.038*
C210.15393 (14)1.04247 (12)0.86660 (11)0.0253 (3)
H210.14760.96920.89300.030*
C220.26485 (13)1.06140 (11)0.85580 (10)0.0194 (2)
C230.65067 (12)0.69625 (11)0.84201 (10)0.0163 (2)
H230.67410.76630.81600.020*
C240.64789 (13)0.66496 (12)0.95505 (10)0.0214 (3)
H24A0.58260.73141.00130.026*
H24B0.62180.59740.98380.026*
C250.78219 (13)0.63550 (13)0.95501 (11)0.0239 (3)
H25A0.80330.70610.93460.029*
H25B0.78000.61021.02740.029*
C260.88789 (13)0.53957 (12)0.87858 (11)0.0241 (3)
H26A0.87240.46640.90360.029*
H26B0.97390.52620.87710.029*
C270.88938 (12)0.57150 (12)0.76716 (11)0.0227 (3)
H27A0.95690.50660.71970.027*
H27B0.91180.64110.73980.027*
C280.75650 (12)0.59640 (11)0.76726 (10)0.0203 (2)
H28A0.73590.52560.79100.024*
H28B0.75860.61820.69460.024*
C290.50206 (12)0.75688 (11)0.70404 (9)0.0165 (2)
H290.54330.67760.67470.020*
C300.58989 (13)0.82273 (12)0.62941 (10)0.0212 (3)
H30A0.54690.90600.64680.025*
H30B0.67410.79000.63790.025*
C310.61324 (13)0.80974 (13)0.51507 (10)0.0246 (3)
H31A0.66670.85410.46660.030*
H31B0.66290.72680.49680.030*
C320.48614 (14)0.85304 (13)0.49863 (11)0.0263 (3)
H32A0.50590.83390.42660.032*
H32B0.44450.93880.50380.032*
C330.39099 (13)0.79931 (12)0.57971 (10)0.0226 (3)
H33A0.42590.71530.56690.027*
H33B0.30650.83660.57140.027*
C340.36958 (12)0.81527 (11)0.69249 (10)0.0183 (2)
H34A0.30830.77940.74420.022*
H34B0.33140.89920.70680.022*
C350.89295 (14)0.32618 (14)0.56997 (11)0.0283 (3)
H350.84670.32080.64850.034*
C360.14817 (15)0.01492 (14)0.26931 (12)0.0309 (3)
H360.19250.10150.26450.037*
Cl10.71624 (3)0.29319 (3)0.82907 (2)0.02431 (7)
Cl20.83623 (5)0.47307 (4)0.52736 (3)0.04050 (10)
Cl31.06121 (4)0.27508 (5)0.53884 (4)0.04713 (12)
Cl40.86009 (4)0.24063 (4)0.51101 (4)0.04124 (10)
Cl50.19955 (5)0.03165 (5)0.34606 (4)0.05000 (12)
Cl60.19249 (5)0.04763 (4)0.14031 (3)0.04382 (11)
Cl70.02108 (4)0.02160 (5)0.32916 (4)0.04959 (12)
P10.49134 (3)0.73346 (3)0.84032 (2)0.01467 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0170 (6)0.0159 (6)0.0181 (5)0.0075 (5)0.0085 (5)0.0031 (4)
C20.0170 (6)0.0171 (6)0.0173 (5)0.0088 (5)0.0077 (5)0.0041 (4)
C30.0191 (6)0.0231 (6)0.0167 (6)0.0103 (5)0.0054 (5)0.0008 (5)
C40.0157 (6)0.0266 (7)0.0226 (6)0.0076 (5)0.0039 (5)0.0024 (5)
C50.0169 (6)0.0264 (7)0.0259 (6)0.0091 (5)0.0099 (5)0.0011 (5)
C60.0187 (6)0.0200 (6)0.0195 (6)0.0096 (5)0.0085 (5)0.0021 (5)
C70.0254 (7)0.0271 (7)0.0238 (6)0.0131 (6)0.0122 (5)0.0010 (5)
C80.0307 (7)0.0274 (7)0.0234 (6)0.0136 (6)0.0098 (6)0.0036 (5)
C90.0229 (7)0.0222 (7)0.0257 (7)0.0078 (5)0.0050 (5)0.0045 (5)
C100.0177 (6)0.0184 (6)0.0243 (6)0.0064 (5)0.0082 (5)0.0001 (5)
C110.0177 (6)0.0166 (6)0.0173 (5)0.0085 (5)0.0067 (5)0.0029 (4)
C120.0170 (6)0.0158 (6)0.0205 (6)0.0033 (5)0.0038 (5)0.0011 (5)
C130.0186 (6)0.0171 (6)0.0163 (5)0.0047 (5)0.0036 (5)0.0032 (4)
C140.0200 (6)0.0232 (7)0.0257 (7)0.0055 (5)0.0068 (5)0.0069 (5)
C150.0263 (7)0.0296 (8)0.0324 (7)0.0149 (6)0.0006 (6)0.0127 (6)
C160.0350 (8)0.0198 (7)0.0262 (7)0.0133 (6)0.0006 (6)0.0037 (5)
C170.0292 (7)0.0175 (6)0.0164 (6)0.0045 (5)0.0037 (5)0.0034 (5)
C180.0422 (9)0.0198 (7)0.0242 (7)0.0002 (6)0.0111 (6)0.0001 (5)
C190.0359 (8)0.0308 (8)0.0293 (7)0.0071 (7)0.0182 (7)0.0083 (6)
C200.0255 (7)0.0329 (8)0.0351 (8)0.0011 (6)0.0148 (6)0.0163 (6)
C210.0228 (7)0.0210 (6)0.0302 (7)0.0027 (5)0.0103 (6)0.0093 (5)
C220.0210 (6)0.0166 (6)0.0160 (5)0.0032 (5)0.0052 (5)0.0050 (4)
C230.0154 (5)0.0160 (6)0.0180 (6)0.0059 (5)0.0065 (5)0.0013 (4)
C240.0183 (6)0.0269 (7)0.0181 (6)0.0066 (5)0.0076 (5)0.0023 (5)
C250.0221 (6)0.0284 (7)0.0248 (6)0.0089 (6)0.0130 (5)0.0007 (5)
C260.0187 (6)0.0226 (7)0.0304 (7)0.0066 (5)0.0119 (5)0.0024 (5)
C270.0155 (6)0.0219 (6)0.0257 (6)0.0049 (5)0.0049 (5)0.0025 (5)
C280.0175 (6)0.0201 (6)0.0215 (6)0.0051 (5)0.0062 (5)0.0053 (5)
C290.0178 (6)0.0166 (6)0.0153 (5)0.0070 (5)0.0070 (5)0.0011 (4)
C300.0224 (6)0.0229 (6)0.0191 (6)0.0118 (5)0.0079 (5)0.0043 (5)
C310.0232 (7)0.0280 (7)0.0180 (6)0.0099 (6)0.0050 (5)0.0018 (5)
C320.0292 (7)0.0310 (7)0.0174 (6)0.0109 (6)0.0100 (5)0.0024 (5)
C330.0235 (6)0.0249 (7)0.0210 (6)0.0077 (5)0.0116 (5)0.0006 (5)
C340.0181 (6)0.0179 (6)0.0182 (6)0.0062 (5)0.0078 (5)0.0013 (5)
C350.0259 (7)0.0374 (8)0.0219 (6)0.0135 (6)0.0069 (6)0.0039 (6)
C360.0313 (8)0.0293 (8)0.0281 (7)0.0107 (6)0.0058 (6)0.0078 (6)
Cl10.02448 (16)0.02486 (16)0.01802 (14)0.00554 (13)0.00729 (12)0.00050 (11)
Cl20.0563 (3)0.0318 (2)0.0359 (2)0.01182 (18)0.02168 (19)0.00852 (16)
Cl30.0290 (2)0.0641 (3)0.0494 (3)0.0193 (2)0.01541 (18)0.0004 (2)
Cl40.0438 (2)0.0338 (2)0.0546 (3)0.01270 (18)0.0253 (2)0.00839 (18)
Cl50.0404 (2)0.0713 (3)0.0443 (2)0.0256 (2)0.00782 (19)0.0232 (2)
Cl60.0471 (2)0.0364 (2)0.0358 (2)0.01224 (19)0.01105 (18)0.00287 (17)
Cl70.0329 (2)0.0653 (3)0.0516 (3)0.0232 (2)0.00251 (19)0.0249 (2)
P10.01423 (14)0.01409 (14)0.01540 (14)0.00529 (11)0.00604 (11)0.00047 (11)
Geometric parameters (Å, º) top
C1—C21.5095 (16)C23—C241.5403 (17)
C1—P11.8262 (12)C23—C281.5405 (17)
C1—H1A0.9900C23—P11.8204 (12)
C1—H1B0.9900C23—H231.0000
C2—C31.3775 (18)C24—C251.5308 (18)
C2—C111.4301 (17)C24—H24A0.9900
C3—C41.4116 (18)C24—H24B0.9900
C3—H30.9500C25—C261.522 (2)
C4—C51.3603 (19)C25—H25A0.9900
C4—H40.9500C25—H25B0.9900
C5—C61.4185 (19)C26—C271.5237 (19)
C5—H50.9500C26—H26A0.9900
C6—C71.4144 (18)C26—H26B0.9900
C6—C111.4253 (17)C27—C281.5269 (18)
C7—C81.362 (2)C27—H27A0.9900
C7—H70.9500C27—H27B0.9900
C8—C91.410 (2)C28—H28A0.9900
C8—H80.9500C28—H28B0.9900
C9—C101.3685 (19)C29—C341.5433 (17)
C9—H90.9500C29—C301.5439 (17)
C10—C111.4236 (18)C29—P11.8264 (12)
C10—H100.9500C29—H291.0000
C12—C131.5097 (17)C30—C311.5344 (18)
C12—P11.8124 (13)C30—H30A0.9900
C12—H12A0.9900C30—H30B0.9900
C12—H12B0.9900C31—C321.526 (2)
C13—C141.3708 (19)C31—H31A0.9900
C13—C221.4335 (18)C31—H31B0.9900
C14—C151.411 (2)C32—C331.5260 (19)
C14—H140.9500C32—H32A0.9900
C15—C161.365 (2)C32—H32B0.9900
C15—H150.9500C33—C341.5305 (17)
C16—C171.413 (2)C33—H33A0.9900
C16—H160.9500C33—H33B0.9900
C17—C221.4239 (19)C34—H34A0.9900
C17—C181.424 (2)C34—H34B0.9900
C18—C191.355 (3)C35—Cl41.7546 (15)
C18—H180.9500C35—Cl31.7571 (15)
C19—C201.401 (2)C35—Cl21.7636 (16)
C19—H190.9500C35—H351.0000
C20—C211.372 (2)C36—Cl71.7548 (16)
C20—H200.9500C36—Cl51.7582 (16)
C21—C221.4247 (19)C36—Cl61.7632 (16)
C21—H210.9500C36—H361.0000
C2—C1—P1111.98 (8)C25—C24—H24B109.5
C2—C1—H1A109.2C23—C24—H24B109.5
P1—C1—H1A109.2H24A—C24—H24B108.1
C2—C1—H1B109.2C26—C25—C24111.50 (11)
P1—C1—H1B109.2C26—C25—H25A109.3
H1A—C1—H1B107.9C24—C25—H25A109.3
C3—C2—C11119.73 (11)C26—C25—H25B109.3
C3—C2—C1118.60 (11)C24—C25—H25B109.3
C11—C2—C1121.46 (11)H25A—C25—H25B108.0
C2—C3—C4121.25 (12)C25—C26—C27111.24 (11)
C2—C3—H3119.4C25—C26—H26A109.4
C4—C3—H3119.4C27—C26—H26A109.4
C5—C4—C3119.85 (12)C25—C26—H26B109.4
C5—C4—H4120.1C27—C26—H26B109.4
C3—C4—H4120.1H26A—C26—H26B108.0
C4—C5—C6120.96 (12)C26—C27—C28110.69 (11)
C4—C5—H5119.5C26—C27—H27A109.5
C6—C5—H5119.5C28—C27—H27A109.5
C7—C6—C5121.09 (12)C26—C27—H27B109.5
C7—C6—C11119.40 (12)C28—C27—H27B109.5
C5—C6—C11119.51 (12)H27A—C27—H27B108.1
C8—C7—C6120.98 (13)C27—C28—C23109.78 (10)
C8—C7—H7119.5C27—C28—H28A109.7
C6—C7—H7119.5C23—C28—H28A109.7
C7—C8—C9120.05 (13)C27—C28—H28B109.7
C7—C8—H8120.0C23—C28—H28B109.7
C9—C8—H8120.0H28A—C28—H28B108.2
C10—C9—C8120.68 (13)C34—C29—C30108.06 (10)
C10—C9—H9119.7C34—C29—P1114.87 (8)
C8—C9—H9119.7C30—C29—P1115.54 (9)
C9—C10—C11120.77 (12)C34—C29—H29105.8
C9—C10—H10119.6C30—C29—H29105.8
C11—C10—H10119.6P1—C29—H29105.8
C10—C11—C6118.10 (11)C31—C30—C29108.37 (11)
C10—C11—C2123.55 (11)C31—C30—H30A110.0
C6—C11—C2118.35 (11)C29—C30—H30A110.0
C13—C12—P1117.85 (9)C31—C30—H30B110.0
C13—C12—H12A107.8C29—C30—H30B110.0
P1—C12—H12A107.8H30A—C30—H30B108.4
C13—C12—H12B107.8C32—C31—C30112.35 (11)
P1—C12—H12B107.8C32—C31—H31A109.1
H12A—C12—H12B107.2C30—C31—H31A109.1
C14—C13—C22119.42 (12)C32—C31—H31B109.1
C14—C13—C12119.94 (12)C30—C31—H31B109.1
C22—C13—C12120.56 (12)H31A—C31—H31B107.9
C13—C14—C15121.69 (13)C31—C32—C33112.32 (11)
C13—C14—H14119.2C31—C32—H32A109.1
C15—C14—H14119.2C33—C32—H32A109.1
C16—C15—C14119.87 (14)C31—C32—H32B109.1
C16—C15—H15120.1C33—C32—H32B109.1
C14—C15—H15120.1H32A—C32—H32B107.9
C15—C16—C17120.65 (13)C32—C33—C34110.81 (11)
C15—C16—H16119.7C32—C33—H33A109.5
C17—C16—H16119.7C34—C33—H33A109.5
C16—C17—C22119.77 (13)C32—C33—H33B109.5
C16—C17—C18121.05 (14)C34—C33—H33B109.5
C22—C17—C18119.17 (14)H33A—C33—H33B108.1
C19—C18—C17121.25 (15)C33—C34—C29108.82 (10)
C19—C18—H18119.4C33—C34—H34A109.9
C17—C18—H18119.4C29—C34—H34A109.9
C18—C19—C20120.16 (14)C33—C34—H34B109.9
C18—C19—H19119.9C29—C34—H34B109.9
C20—C19—H19119.9H34A—C34—H34B108.3
C21—C20—C19120.53 (15)Cl4—C35—Cl3110.35 (8)
C21—C20—H20119.7Cl4—C35—Cl2110.55 (8)
C19—C20—H20119.7Cl3—C35—Cl2109.80 (8)
C20—C21—C22121.23 (14)Cl4—C35—H35108.7
C20—C21—H21119.4Cl3—C35—H35108.7
C22—C21—H21119.4Cl2—C35—H35108.7
C17—C22—C21117.63 (12)Cl7—C36—Cl5110.33 (8)
C17—C22—C13118.54 (12)Cl7—C36—Cl6110.53 (9)
C21—C22—C13123.83 (12)Cl5—C36—Cl6110.16 (9)
C24—C23—C28110.48 (10)Cl7—C36—H36108.6
C24—C23—P1111.40 (8)Cl5—C36—H36108.6
C28—C23—P1111.39 (8)Cl6—C36—H36108.6
C24—C23—H23107.8C12—P1—C23110.81 (6)
C28—C23—H23107.8C12—P1—C1105.26 (6)
P1—C23—H23107.8C23—P1—C1107.20 (6)
C25—C24—C23110.61 (10)C12—P1—C29113.35 (6)
C25—C24—H24A109.5C23—P1—C29110.05 (6)
C23—C24—H24A109.5C1—P1—C29109.88 (6)
P1—C1—C2—C382.43 (12)C20—C21—C22—C171.1 (2)
P1—C1—C2—C1192.37 (12)C20—C21—C22—C13179.82 (13)
C11—C2—C3—C45.77 (19)C14—C13—C22—C173.00 (18)
C1—C2—C3—C4169.12 (12)C12—C13—C22—C17179.68 (11)
C2—C3—C4—C50.9 (2)C14—C13—C22—C21176.03 (13)
C3—C4—C5—C63.7 (2)C12—C13—C22—C210.64 (19)
C4—C5—C6—C7177.41 (13)C28—C23—C24—C2556.37 (14)
C4—C5—C6—C113.3 (2)P1—C23—C24—C25179.26 (9)
C5—C6—C7—C8179.46 (13)C23—C24—C25—C2654.96 (15)
C11—C6—C7—C80.2 (2)C24—C25—C26—C2755.49 (15)
C6—C7—C8—C91.2 (2)C25—C26—C27—C2857.30 (15)
C7—C8—C9—C101.5 (2)C26—C27—C28—C2358.46 (14)
C8—C9—C10—C110.3 (2)C24—C23—C28—C2758.14 (14)
C9—C10—C11—C61.03 (19)P1—C23—C28—C27177.48 (9)
C9—C10—C11—C2177.99 (12)C34—C29—C30—C3162.81 (13)
C7—C6—C11—C101.30 (18)P1—C29—C30—C31166.94 (9)
C5—C6—C11—C10179.43 (12)C29—C30—C31—C3256.70 (15)
C7—C6—C11—C2177.78 (12)C30—C31—C32—C3351.85 (16)
C5—C6—C11—C21.49 (18)C31—C32—C33—C3452.53 (16)
C3—C2—C11—C10175.03 (12)C32—C33—C34—C2959.07 (14)
C1—C2—C11—C1010.23 (18)C30—C29—C34—C3364.66 (13)
C3—C2—C11—C65.94 (17)P1—C29—C34—C33164.72 (9)
C1—C2—C11—C6168.79 (11)C13—C12—P1—C2375.13 (11)
P1—C12—C13—C1470.57 (15)C13—C12—P1—C1169.30 (10)
P1—C12—C13—C22112.77 (12)C13—C12—P1—C2949.18 (12)
C22—C13—C14—C152.2 (2)C24—C23—P1—C1259.03 (10)
C12—C13—C14—C15178.90 (12)C28—C23—P1—C12177.12 (9)
C13—C14—C15—C160.1 (2)C24—C23—P1—C155.33 (10)
C14—C15—C16—C171.2 (2)C28—C23—P1—C168.52 (10)
C15—C16—C17—C220.3 (2)C24—C23—P1—C29174.80 (9)
C15—C16—C17—C18178.96 (14)C28—C23—P1—C2950.95 (10)
C16—C17—C18—C19178.01 (14)C2—C1—P1—C1275.77 (10)
C22—C17—C18—C191.3 (2)C2—C1—P1—C23166.20 (9)
C17—C18—C19—C200.3 (2)C2—C1—P1—C2946.61 (10)
C18—C19—C20—C211.2 (2)C34—C29—P1—C1242.18 (11)
C19—C20—C21—C220.5 (2)C30—C29—P1—C1284.71 (10)
C16—C17—C22—C21177.34 (12)C34—C29—P1—C23166.90 (9)
C18—C17—C22—C211.99 (18)C30—C29—P1—C2340.01 (11)
C16—C17—C22—C131.76 (18)C34—C29—P1—C175.27 (10)
C18—C17—C22—C13178.92 (12)C30—C29—P1—C1157.84 (9)

Experimental details

Crystal data
Chemical formulaC34H40P+·Cl·2CHCl3
Mr753.82
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)12.3079 (2), 12.7150 (2), 14.0310 (3)
α, β, γ (°)77.785 (1), 64.242 (1), 64.738 (1)
V3)1787.56 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.63
Crystal size (mm)0.43 × 0.30 × 0.19
Data collection
DiffractometerBruker Kappa APEXII DUO
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.96, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
40097, 8871, 7562
Rint0.025
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.080, 1.03
No. of reflections8871
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.44

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We thank Dr W. Baumann, and Mrs S. Buchholz (both of LIKAT) for their support.

References

First citationBrady, E. D., Hanusa, T. P., Pink, M. & Young, V. G. Jr (2000). Inorg. Chem. 39, 6028-6037.  Web of Science CSD CrossRef PubMed CAS
First citationBruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDornhaus, F., Lerner, H.-W. & Bolte, M. (2005). Acta Cryst. E61, o1657–o1658.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationStaples, R. J., Carlson, T., Wang, S. & Fackler, J. P. (1995). Acta Cryst. C51, 498–500.  CSD CrossRef CAS Web of Science IUCr Journals

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