Pentyl­tri­phenyl­phospho­nium bromide

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.

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

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Computing details

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)

Crystal data

C23H26P^+·Br^−	F(000) = 856
Mr = 413.32	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 20273 reflections
a = 11.6338 (4) Å	θ = 3.9–68.2°
b = 10.3522 (3) Å	µ = 3.53 mm^−1
c = 17.2434 (5) Å	T = 102 K
β = 104.393 (2)°	Prism, colorless
V = 2011.54 (11) Å^3	0.28 × 0.18 × 0.15 mm
Z = 4

Data collection

Bruker CCD plate diffractometer	3684 independent reflections
Radiation source: rotating anode	2694 reflections with I > 2σ(I)
Göbel focusing mirrors monochromator	Rint = 0.098
Detector resolution: 17 pixels mm^-1	θmax = 68.4°, θmin = 3.9°
ω scans	h = −14→13
Absorption correction: multi-scan (Blessing, 1995)	k = −8→12
Tmin = 0.36, Tmax = 0.59	l = −20→20
19502 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0453P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.089	(Δ/σ)max = 0.001
S = 0.94	Δρmax = 0.71 e Å^−3
3684 reflections	Δρmin = −0.43 e Å^−3
226 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C11	0.3351 (2)	0.5722 (3)	0.50799 (16)	0.0226 (7)
H11A	0.3418	0.5083	0.4667	0.027*
H11B	0.4155	0.6065	0.532	0.027*
C12	0.2886 (3)	0.5041 (3)	0.57335 (16)	0.0270 (7)
H12A	0.2915	0.565	0.6181	0.032*
H12B	0.2047	0.4791	0.5511	0.032*
C13	0.3612 (3)	0.3834 (3)	0.60545 (16)	0.0283 (7)
H13A	0.4462	0.4075	0.6215	0.034*
H13B	0.3384	0.3538	0.6541	0.034*
C14	0.3462 (3)	0.2705 (3)	0.54635 (17)	0.0277 (7)
H14A	0.3676	0.2997	0.4971	0.033*
H14B	0.4015	0.2004	0.5703	0.033*
C15	0.2213 (3)	0.2181 (3)	0.5243 (2)	0.0429 (9)
H15A	0.2163	0.1466	0.4864	0.064*
H15B	0.1662	0.2867	0.4997	0.064*
H15C	0.2003	0.1869	0.5727	0.064*
C21	0.3150 (2)	0.8034 (3)	0.40273 (16)	0.0228 (7)
C22	0.3478 (2)	0.7465 (3)	0.33840 (15)	0.0256 (7)
H22	0.3338	0.6573	0.3272	0.031*
C23	0.4012 (3)	0.8218 (4)	0.29077 (17)	0.0324 (8)
H23	0.4255	0.7834	0.2474	0.039*
C24	0.4192 (3)	0.9522 (4)	0.30585 (18)	0.0339 (8)
H24	0.4548	1.0031	0.2723	0.041*
C25	0.3858 (3)	1.0093 (3)	0.36970 (19)	0.0342 (8)
H25	0.3982	1.099	0.3801	0.041*
C26	0.3338 (3)	0.9335 (3)	0.41808 (18)	0.0291 (7)
H26	0.3111	0.9716	0.4622	0.035*
C31	0.1081 (2)	0.6423 (3)	0.39306 (15)	0.0227 (7)
C32	0.0899 (3)	0.5108 (3)	0.37978 (16)	0.0284 (8)
H32	0.1474	0.4506	0.4072	0.034*
C33	−0.0130 (3)	0.4673 (3)	0.32614 (18)	0.0367 (8)
H33	−0.0261	0.3773	0.3175	0.044*
C34	−0.0960 (3)	0.5548 (4)	0.28550 (18)	0.0391 (9)
H34	−0.1664	0.5244	0.2495	0.047*
C35	−0.0775 (3)	0.6868 (4)	0.29674 (18)	0.0361 (8)
H35	−0.1343	0.7467	0.2681	0.043*
C36	0.0248 (3)	0.7302 (3)	0.35034 (16)	0.0313 (8)
H36	0.0384	0.8203	0.3581	0.038*
C41	0.2044 (3)	0.7990 (3)	0.53843 (15)	0.0225 (7)
C42	0.2969 (3)	0.8541 (3)	0.59673 (17)	0.0306 (8)
H42	0.3768	0.8415	0.5943	0.037*
C43	0.2724 (3)	0.9264 (3)	0.65746 (17)	0.0312 (8)
H43	0.3355	0.9656	0.696	0.037*
C44	0.1569 (3)	0.9427 (3)	0.66294 (17)	0.0319 (8)
H44	0.1407	0.9918	0.7056	0.038*
C45	0.0652 (3)	0.8876 (3)	0.60633 (18)	0.0353 (8)
H45	−0.0143	0.8984	0.6102	0.042*
C46	0.0885 (3)	0.8161 (3)	0.54344 (17)	0.0327 (8)
H46	0.025	0.7793	0.5041	0.039*
Br	0.62952 (3)	0.63696 (3)	0.668080 (17)	0.02736 (12)
P	0.24074 (7)	0.70306 (8)	0.46085 (4)	0.02103 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0186 (16)	0.0215 (18)	0.0268 (15)	0.0039 (14)	0.0036 (12)	0.0012 (13)
C12	0.0302 (18)	0.024 (2)	0.0268 (15)	0.0025 (15)	0.0076 (13)	−0.0001 (13)
C13	0.0314 (18)	0.025 (2)	0.0268 (16)	0.0012 (15)	0.0044 (13)	0.0026 (13)
C14	0.0259 (17)	0.023 (2)	0.0329 (16)	0.0044 (15)	0.0052 (13)	0.0041 (14)
C15	0.033 (2)	0.025 (2)	0.066 (2)	0.0010 (17)	0.0035 (17)	0.0001 (17)
C21	0.0181 (16)	0.0221 (19)	0.0263 (15)	−0.0036 (14)	0.0019 (12)	0.0029 (13)
C22	0.0222 (17)	0.0230 (19)	0.0301 (16)	−0.0017 (14)	0.0039 (13)	0.0003 (13)
C23	0.0263 (18)	0.045 (2)	0.0267 (16)	−0.0009 (16)	0.0076 (13)	0.0059 (15)
C24	0.0212 (17)	0.042 (2)	0.0355 (17)	−0.0032 (16)	0.0010 (14)	0.0170 (17)
C25	0.032 (2)	0.018 (2)	0.0485 (19)	−0.0027 (15)	0.0028 (15)	0.0066 (15)
C26	0.0291 (18)	0.022 (2)	0.0369 (17)	0.0004 (15)	0.0088 (14)	0.0005 (14)
C31	0.0218 (16)	0.0258 (19)	0.0216 (14)	−0.0013 (14)	0.0078 (12)	−0.0005 (13)
C32	0.0320 (19)	0.025 (2)	0.0271 (15)	−0.0035 (15)	0.0055 (13)	0.0003 (14)
C33	0.042 (2)	0.031 (2)	0.0373 (18)	−0.0183 (18)	0.0096 (16)	−0.0090 (16)
C34	0.0274 (19)	0.058 (3)	0.0311 (17)	−0.0137 (19)	0.0063 (14)	−0.0080 (17)
C35	0.0212 (18)	0.049 (3)	0.0350 (17)	0.0055 (17)	0.0015 (14)	0.0049 (16)
C36	0.0296 (19)	0.031 (2)	0.0323 (16)	0.0013 (16)	0.0065 (14)	−0.0001 (15)
C41	0.0230 (17)	0.0199 (18)	0.0254 (15)	0.0025 (14)	0.0073 (12)	−0.0011 (13)
C42	0.0272 (18)	0.030 (2)	0.0330 (16)	0.0017 (16)	0.0052 (13)	−0.0040 (15)
C43	0.0330 (19)	0.029 (2)	0.0286 (16)	−0.0025 (16)	0.0026 (13)	−0.0073 (14)
C44	0.040 (2)	0.028 (2)	0.0291 (16)	0.0046 (16)	0.0108 (15)	−0.0031 (14)
C45	0.0286 (19)	0.040 (2)	0.0403 (19)	0.0059 (17)	0.0135 (15)	−0.0062 (16)
C46	0.0272 (18)	0.035 (2)	0.0339 (17)	−0.0036 (16)	0.0038 (14)	−0.0079 (15)
Br	0.0332 (2)	0.0206 (2)	0.02844 (18)	0.00006 (15)	0.00786 (13)	0.00176 (13)
P	0.0195 (4)	0.0179 (5)	0.0252 (4)	0.0002 (3)	0.0047 (3)	−0.0010 (3)

Geometric parameters (Å, º)

C11—C12	1.537 (4)	C25—H25	0.95
C11—P	1.804 (3)	C26—H26	0.95
C11—H11A	0.99	C31—C32	1.388 (4)
C11—H11B	0.99	C31—C36	1.397 (4)
C12—C13	1.533 (4)	C31—P	1.802 (3)
C12—H12A	0.99	C32—C33	1.392 (4)
C12—H12B	0.99	C32—H32	0.95
C13—C14	1.532 (4)	C33—C34	1.381 (5)
C13—H13A	0.99	C33—H33	0.95
C13—H13B	0.99	C34—C35	1.390 (5)
C14—C15	1.508 (4)	C34—H34	0.95
C14—H14A	0.99	C35—C36	1.388 (4)
C14—H14B	0.99	C35—H35	0.95
C15—H15A	0.98	C36—H36	0.95
C15—H15B	0.98	C41—C46	1.384 (4)
C15—H15C	0.98	C41—C42	1.399 (4)
C21—C26	1.380 (4)	C41—P	1.799 (3)
C21—C22	1.390 (4)	C42—C43	1.374 (4)
C21—P	1.805 (3)	C42—H42	0.95
C22—C23	1.386 (4)	C43—C44	1.381 (4)
C22—H22	0.95	C43—H43	0.95
C23—C24	1.381 (5)	C44—C45	1.378 (4)
C23—H23	0.95	C44—H44	0.95
C24—C25	1.388 (5)	C45—C46	1.394 (4)
C24—H24	0.95	C45—H45	0.95
C25—C26	1.388 (4)	C46—H46	0.95
C12—C11—P	112.9 (2)	C21—C26—C25	120.6 (3)
C12—C11—H11A	109	C21—C26—H26	119.7
P—C11—H11A	109	C25—C26—H26	119.7
C12—C11—H11B	109	C32—C31—C36	119.6 (3)
P—C11—H11B	109	C32—C31—P	121.3 (2)
H11A—C11—H11B	107.8	C36—C31—P	119.0 (2)
C13—C12—C11	112.1 (2)	C31—C32—C33	119.8 (3)
C13—C12—H12A	109.2	C31—C32—H32	120.1
C11—C12—H12A	109.2	C33—C32—H32	120.1
C13—C12—H12B	109.2	C34—C33—C32	120.1 (3)
C11—C12—H12B	109.2	C34—C33—H33	119.9
H12A—C12—H12B	107.9	C32—C33—H33	119.9
C14—C13—C12	114.8 (2)	C33—C34—C35	120.7 (3)
C14—C13—H13A	108.6	C33—C34—H34	119.7
C12—C13—H13A	108.6	C35—C34—H34	119.7
C14—C13—H13B	108.6	C36—C35—C34	119.2 (3)
C12—C13—H13B	108.6	C36—C35—H35	120.4
H13A—C13—H13B	107.5	C34—C35—H35	120.4
C15—C14—C13	112.7 (3)	C35—C36—C31	120.5 (3)
C15—C14—H14A	109.1	C35—C36—H36	119.7
C13—C14—H14A	109.1	C31—C36—H36	119.7
C15—C14—H14B	109.1	C46—C41—C42	119.4 (3)
C13—C14—H14B	109.1	C46—C41—P	122.0 (2)
H14A—C14—H14B	107.8	C42—C41—P	118.6 (2)
C14—C15—H15A	109.5	C43—C42—C41	120.1 (3)
C14—C15—H15B	109.5	C43—C42—H42	119.9
H15A—C15—H15B	109.5	C41—C42—H42	119.9
C14—C15—H15C	109.5	C42—C43—C44	120.6 (3)
H15A—C15—H15C	109.5	C42—C43—H43	119.7
H15B—C15—H15C	109.5	C44—C43—H43	119.7
C26—C21—C22	120.3 (3)	C45—C44—C43	119.8 (3)
C26—C21—P	122.0 (2)	C45—C44—H44	120.1
C22—C21—P	117.6 (2)	C43—C44—H44	120.1
C23—C22—C21	119.2 (3)	C44—C45—C46	120.3 (3)
C23—C22—H22	120.4	C44—C45—H45	119.9
C21—C22—H22	120.4	C46—C45—H45	119.9
C24—C23—C22	120.5 (3)	C41—C46—C45	119.9 (3)
C24—C23—H23	119.8	C41—C46—H46	120.1
C22—C23—H23	119.8	C45—C46—H46	120.1
C23—C24—C25	120.4 (3)	C41—P—C31	110.68 (13)
C23—C24—H24	119.8	C41—P—C11	107.97 (13)
C25—C24—H24	119.8	C31—P—C11	110.93 (14)
C24—C25—C26	119.0 (3)	C41—P—C21	109.18 (14)
C24—C25—H25	120.5	C31—P—C21	106.95 (13)
C26—C25—H25	120.5	C11—P—C21	111.14 (14)
P—C11—C12—C13	173.0 (2)	C42—C41—C46—C45	−0.1 (5)
C11—C12—C13—C14	−69.6 (3)	P—C41—C46—C45	177.7 (3)
C12—C13—C14—C15	−63.8 (3)	C44—C45—C46—C41	0.9 (5)
C26—C21—C22—C23	1.0 (4)	C46—C41—P—C31	2.1 (3)
P—C21—C22—C23	177.7 (2)	C42—C41—P—C31	179.9 (2)
C21—C22—C23—C24	−1.4 (4)	C46—C41—P—C11	−119.5 (3)
C22—C23—C24—C25	1.0 (5)	C42—C41—P—C11	58.3 (3)
C23—C24—C25—C26	0.0 (5)	C46—C41—P—C21	119.5 (3)
C22—C21—C26—C25	0.0 (4)	C42—C41—P—C21	−62.6 (3)
P—C21—C26—C25	−176.7 (2)	C32—C31—P—C41	−122.2 (2)
C24—C25—C26—C21	−0.4 (5)	C36—C31—P—C41	60.8 (3)
C36—C31—C32—C33	−2.2 (4)	C32—C31—P—C11	−2.4 (3)
P—C31—C32—C33	−179.1 (2)	C36—C31—P—C11	−179.3 (2)
C31—C32—C33—C34	0.8 (4)	C32—C31—P—C21	118.9 (2)
C32—C33—C34—C35	0.8 (5)	C36—C31—P—C21	−58.0 (3)
C33—C34—C35—C36	−0.9 (5)	C12—C11—P—C41	46.6 (2)
C34—C35—C36—C31	−0.5 (4)	C12—C11—P—C31	−74.9 (2)
C32—C31—C36—C35	2.1 (4)	C12—C11—P—C21	166.3 (2)
P—C31—C36—C35	179.0 (2)	C26—C21—P—C41	−1.8 (3)
C46—C41—C42—C43	−1.2 (5)	C22—C21—P—C41	−178.6 (2)
P—C41—C42—C43	−179.1 (2)	C26—C21—P—C31	118.0 (2)
C41—C42—C43—C44	1.7 (5)	C22—C21—P—C31	−58.8 (3)
C42—C43—C44—C45	−1.0 (5)	C26—C21—P—C11	−120.8 (3)
C43—C44—C45—C46	−0.3 (5)	C22—C21—P—C11	62.5 (3)