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At 102 K, the two torsion angles of the pentyl group nearest to P in the title compound, C23H26P+·Br-, correspond to the extended conformation. However, the remaining torsions are gauche-. The phenyl rings are in the propeller configuration usually found in this family of tri­phenyl­phospho­nium compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029769/ac6135sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029769/ac6135Isup2.hkl
Contains datablock I

CCDC reference: 259603

Key indicators

  • Single-crystal X-ray study
  • T = 102 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.089
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: PROTEUM (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 publication routines (Farrugia, 1999).

(I) top
Crystal data top
C23H26P+·BrF(000) = 856
Mr = 413.32Dx = 1.365 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 20273 reflections
a = 11.6338 (4) Åθ = 3.9–68.2°
b = 10.3522 (3) ŵ = 3.53 mm1
c = 17.2434 (5) ÅT = 102 K
β = 104.393 (2)°Prism, colorless
V = 2011.54 (11) Å30.28 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker CCD plate
diffractometer
3684 independent reflections
Radiation source: rotating anode2694 reflections with I > 2σ(I)
Göbel focusing mirrors monochromatorRint = 0.098
Detector resolution: 17 pixels mm-1θmax = 68.4°, θmin = 3.9°
ω scansh = 1413
Absorption correction: multi-scan
(Blessing, 1995)
k = 812
Tmin = 0.36, Tmax = 0.59l = 2020
19502 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089(Δ/σ)max = 0.001
S = 0.94Δρmax = 0.71 e Å3
3684 reflectionsΔρmin = 0.43 e Å3
226 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections.

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
C110.3351 (2)0.5722 (3)0.50799 (16)0.0226 (7)
H11A0.34180.50830.46670.027*
H11B0.41550.60650.5320.027*
C120.2886 (3)0.5041 (3)0.57335 (16)0.0270 (7)
H12A0.29150.5650.61810.032*
H12B0.20470.47910.55110.032*
C130.3612 (3)0.3834 (3)0.60545 (16)0.0283 (7)
H13A0.44620.40750.62150.034*
H13B0.33840.35380.65410.034*
C140.3462 (3)0.2705 (3)0.54635 (17)0.0277 (7)
H14A0.36760.29970.49710.033*
H14B0.40150.20040.57030.033*
C150.2213 (3)0.2181 (3)0.5243 (2)0.0429 (9)
H15A0.21630.14660.48640.064*
H15B0.16620.28670.49970.064*
H15C0.20030.18690.57270.064*
C210.3150 (2)0.8034 (3)0.40273 (16)0.0228 (7)
C220.3478 (2)0.7465 (3)0.33840 (15)0.0256 (7)
H220.33380.65730.32720.031*
C230.4012 (3)0.8218 (4)0.29077 (17)0.0324 (8)
H230.42550.78340.24740.039*
C240.4192 (3)0.9522 (4)0.30585 (18)0.0339 (8)
H240.45481.00310.27230.041*
C250.3858 (3)1.0093 (3)0.36970 (19)0.0342 (8)
H250.39821.0990.38010.041*
C260.3338 (3)0.9335 (3)0.41808 (18)0.0291 (7)
H260.31110.97160.46220.035*
C310.1081 (2)0.6423 (3)0.39306 (15)0.0227 (7)
C320.0899 (3)0.5108 (3)0.37978 (16)0.0284 (8)
H320.14740.45060.40720.034*
C330.0130 (3)0.4673 (3)0.32614 (18)0.0367 (8)
H330.02610.37730.31750.044*
C340.0960 (3)0.5548 (4)0.28550 (18)0.0391 (9)
H340.16640.52440.24950.047*
C350.0775 (3)0.6868 (4)0.29674 (18)0.0361 (8)
H350.13430.74670.26810.043*
C360.0248 (3)0.7302 (3)0.35034 (16)0.0313 (8)
H360.03840.82030.35810.038*
C410.2044 (3)0.7990 (3)0.53843 (15)0.0225 (7)
C420.2969 (3)0.8541 (3)0.59673 (17)0.0306 (8)
H420.37680.84150.59430.037*
C430.2724 (3)0.9264 (3)0.65746 (17)0.0312 (8)
H430.33550.96560.6960.037*
C440.1569 (3)0.9427 (3)0.66294 (17)0.0319 (8)
H440.14070.99180.70560.038*
C450.0652 (3)0.8876 (3)0.60633 (18)0.0353 (8)
H450.01430.89840.61020.042*
C460.0885 (3)0.8161 (3)0.54344 (17)0.0327 (8)
H460.0250.77930.50410.039*
Br0.62952 (3)0.63696 (3)0.668080 (17)0.02736 (12)
P0.24074 (7)0.70306 (8)0.46085 (4)0.02103 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0186 (16)0.0215 (18)0.0268 (15)0.0039 (14)0.0036 (12)0.0012 (13)
C120.0302 (18)0.024 (2)0.0268 (15)0.0025 (15)0.0076 (13)0.0001 (13)
C130.0314 (18)0.025 (2)0.0268 (16)0.0012 (15)0.0044 (13)0.0026 (13)
C140.0259 (17)0.023 (2)0.0329 (16)0.0044 (15)0.0052 (13)0.0041 (14)
C150.033 (2)0.025 (2)0.066 (2)0.0010 (17)0.0035 (17)0.0001 (17)
C210.0181 (16)0.0221 (19)0.0263 (15)0.0036 (14)0.0019 (12)0.0029 (13)
C220.0222 (17)0.0230 (19)0.0301 (16)0.0017 (14)0.0039 (13)0.0003 (13)
C230.0263 (18)0.045 (2)0.0267 (16)0.0009 (16)0.0076 (13)0.0059 (15)
C240.0212 (17)0.042 (2)0.0355 (17)0.0032 (16)0.0010 (14)0.0170 (17)
C250.032 (2)0.018 (2)0.0485 (19)0.0027 (15)0.0028 (15)0.0066 (15)
C260.0291 (18)0.022 (2)0.0369 (17)0.0004 (15)0.0088 (14)0.0005 (14)
C310.0218 (16)0.0258 (19)0.0216 (14)0.0013 (14)0.0078 (12)0.0005 (13)
C320.0320 (19)0.025 (2)0.0271 (15)0.0035 (15)0.0055 (13)0.0003 (14)
C330.042 (2)0.031 (2)0.0373 (18)0.0183 (18)0.0096 (16)0.0090 (16)
C340.0274 (19)0.058 (3)0.0311 (17)0.0137 (19)0.0063 (14)0.0080 (17)
C350.0212 (18)0.049 (3)0.0350 (17)0.0055 (17)0.0015 (14)0.0049 (16)
C360.0296 (19)0.031 (2)0.0323 (16)0.0013 (16)0.0065 (14)0.0001 (15)
C410.0230 (17)0.0199 (18)0.0254 (15)0.0025 (14)0.0073 (12)0.0011 (13)
C420.0272 (18)0.030 (2)0.0330 (16)0.0017 (16)0.0052 (13)0.0040 (15)
C430.0330 (19)0.029 (2)0.0286 (16)0.0025 (16)0.0026 (13)0.0073 (14)
C440.040 (2)0.028 (2)0.0291 (16)0.0046 (16)0.0108 (15)0.0031 (14)
C450.0286 (19)0.040 (2)0.0403 (19)0.0059 (17)0.0135 (15)0.0062 (16)
C460.0272 (18)0.035 (2)0.0339 (17)0.0036 (16)0.0038 (14)0.0079 (15)
Br0.0332 (2)0.0206 (2)0.02844 (18)0.00006 (15)0.00786 (13)0.00176 (13)
P0.0195 (4)0.0179 (5)0.0252 (4)0.0002 (3)0.0047 (3)0.0010 (3)
Geometric parameters (Å, º) top
C11—C121.537 (4)C25—H250.95
C11—P1.804 (3)C26—H260.95
C11—H11A0.99C31—C321.388 (4)
C11—H11B0.99C31—C361.397 (4)
C12—C131.533 (4)C31—P1.802 (3)
C12—H12A0.99C32—C331.392 (4)
C12—H12B0.99C32—H320.95
C13—C141.532 (4)C33—C341.381 (5)
C13—H13A0.99C33—H330.95
C13—H13B0.99C34—C351.390 (5)
C14—C151.508 (4)C34—H340.95
C14—H14A0.99C35—C361.388 (4)
C14—H14B0.99C35—H350.95
C15—H15A0.98C36—H360.95
C15—H15B0.98C41—C461.384 (4)
C15—H15C0.98C41—C421.399 (4)
C21—C261.380 (4)C41—P1.799 (3)
C21—C221.390 (4)C42—C431.374 (4)
C21—P1.805 (3)C42—H420.95
C22—C231.386 (4)C43—C441.381 (4)
C22—H220.95C43—H430.95
C23—C241.381 (5)C44—C451.378 (4)
C23—H230.95C44—H440.95
C24—C251.388 (5)C45—C461.394 (4)
C24—H240.95C45—H450.95
C25—C261.388 (4)C46—H460.95
C12—C11—P112.9 (2)C21—C26—C25120.6 (3)
C12—C11—H11A109C21—C26—H26119.7
P—C11—H11A109C25—C26—H26119.7
C12—C11—H11B109C32—C31—C36119.6 (3)
P—C11—H11B109C32—C31—P121.3 (2)
H11A—C11—H11B107.8C36—C31—P119.0 (2)
C13—C12—C11112.1 (2)C31—C32—C33119.8 (3)
C13—C12—H12A109.2C31—C32—H32120.1
C11—C12—H12A109.2C33—C32—H32120.1
C13—C12—H12B109.2C34—C33—C32120.1 (3)
C11—C12—H12B109.2C34—C33—H33119.9
H12A—C12—H12B107.9C32—C33—H33119.9
C14—C13—C12114.8 (2)C33—C34—C35120.7 (3)
C14—C13—H13A108.6C33—C34—H34119.7
C12—C13—H13A108.6C35—C34—H34119.7
C14—C13—H13B108.6C36—C35—C34119.2 (3)
C12—C13—H13B108.6C36—C35—H35120.4
H13A—C13—H13B107.5C34—C35—H35120.4
C15—C14—C13112.7 (3)C35—C36—C31120.5 (3)
C15—C14—H14A109.1C35—C36—H36119.7
C13—C14—H14A109.1C31—C36—H36119.7
C15—C14—H14B109.1C46—C41—C42119.4 (3)
C13—C14—H14B109.1C46—C41—P122.0 (2)
H14A—C14—H14B107.8C42—C41—P118.6 (2)
C14—C15—H15A109.5C43—C42—C41120.1 (3)
C14—C15—H15B109.5C43—C42—H42119.9
H15A—C15—H15B109.5C41—C42—H42119.9
C14—C15—H15C109.5C42—C43—C44120.6 (3)
H15A—C15—H15C109.5C42—C43—H43119.7
H15B—C15—H15C109.5C44—C43—H43119.7
C26—C21—C22120.3 (3)C45—C44—C43119.8 (3)
C26—C21—P122.0 (2)C45—C44—H44120.1
C22—C21—P117.6 (2)C43—C44—H44120.1
C23—C22—C21119.2 (3)C44—C45—C46120.3 (3)
C23—C22—H22120.4C44—C45—H45119.9
C21—C22—H22120.4C46—C45—H45119.9
C24—C23—C22120.5 (3)C41—C46—C45119.9 (3)
C24—C23—H23119.8C41—C46—H46120.1
C22—C23—H23119.8C45—C46—H46120.1
C23—C24—C25120.4 (3)C41—P—C31110.68 (13)
C23—C24—H24119.8C41—P—C11107.97 (13)
C25—C24—H24119.8C31—P—C11110.93 (14)
C24—C25—C26119.0 (3)C41—P—C21109.18 (14)
C24—C25—H25120.5C31—P—C21106.95 (13)
C26—C25—H25120.5C11—P—C21111.14 (14)
P—C11—C12—C13173.0 (2)C42—C41—C46—C450.1 (5)
C11—C12—C13—C1469.6 (3)P—C41—C46—C45177.7 (3)
C12—C13—C14—C1563.8 (3)C44—C45—C46—C410.9 (5)
C26—C21—C22—C231.0 (4)C46—C41—P—C312.1 (3)
P—C21—C22—C23177.7 (2)C42—C41—P—C31179.9 (2)
C21—C22—C23—C241.4 (4)C46—C41—P—C11119.5 (3)
C22—C23—C24—C251.0 (5)C42—C41—P—C1158.3 (3)
C23—C24—C25—C260.0 (5)C46—C41—P—C21119.5 (3)
C22—C21—C26—C250.0 (4)C42—C41—P—C2162.6 (3)
P—C21—C26—C25176.7 (2)C32—C31—P—C41122.2 (2)
C24—C25—C26—C210.4 (5)C36—C31—P—C4160.8 (3)
C36—C31—C32—C332.2 (4)C32—C31—P—C112.4 (3)
P—C31—C32—C33179.1 (2)C36—C31—P—C11179.3 (2)
C31—C32—C33—C340.8 (4)C32—C31—P—C21118.9 (2)
C32—C33—C34—C350.8 (5)C36—C31—P—C2158.0 (3)
C33—C34—C35—C360.9 (5)C12—C11—P—C4146.6 (2)
C34—C35—C36—C310.5 (4)C12—C11—P—C3174.9 (2)
C32—C31—C36—C352.1 (4)C12—C11—P—C21166.3 (2)
P—C31—C36—C35179.0 (2)C26—C21—P—C411.8 (3)
C46—C41—C42—C431.2 (5)C22—C21—P—C41178.6 (2)
P—C41—C42—C43179.1 (2)C26—C21—P—C31118.0 (2)
C41—C42—C43—C441.7 (5)C22—C21—P—C3158.8 (3)
C42—C43—C44—C451.0 (5)C26—C21—P—C11120.8 (3)
C43—C44—C45—C460.3 (5)C22—C21—P—C1162.5 (3)
 

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