Tri­phenyl­(propyl)­phospho­nium bromide

At 102 K, the propyl group of the title compound, C₂₁H₂₂BrP, is in the extended conformation. The phenyl rings are in the propeller configuration usually found in this family of tri­phenyl­phospho­nium compounds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.090
• Data-to-parameter ratio = 16.0

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).

Triphenyl(propyl)phosphonium bromide

Crystal data

C21H22P^+·Br^−	F(000) = 792
Mr = 385.27	Dx = 1.387 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 18618 reflections
a = 10.7932 (2) Å	θ = 5.1–68.2°
b = 9.8543 (2) Å	µ = 3.81 mm^−1
c = 17.8692 (3) Å	T = 100 K
β = 103.967 (1)°	Prism, colorless
V = 1844.37 (6) Å^3	0.35 × 0.35 × 0.3 mm
Z = 4

Data collection

Bruker AXS CCD diffractometer	2945 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.098
Göbel focusing mirrors monochromator	θmax = 68.3°, θmin = 4.2°
Detector resolution: 17 pixels mm^-1	h = −12→10
ω scans	k = −11→8
17895 measured reflections	l = −19→21
3349 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.0077P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.090	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.64 e Å^−3
3349 reflections	Δρmin = −0.48 e Å^−3
209 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	0.81830 (19)	0.4564 (2)	1.00233 (11)	0.0199 (4)
H11A	0.9026	0.424	1.0322	0.024*
H11B	0.8324	0.5098	0.9582	0.024*
C12	0.7605 (2)	0.5500 (2)	1.05408 (12)	0.0253 (5)
H12A	0.6662	0.5448	1.038	0.03*
H12B	0.7878	0.5187	1.1082	0.03*
C13	0.8025 (3)	0.6963 (3)	1.04889 (17)	0.0447 (7)
H13A	0.896	0.7008	1.0618	0.067*
H13B	0.7699	0.7523	1.0852	0.067*
H13C	0.7688	0.7301	0.9963	0.067*
C21	0.80830 (18)	0.1942 (2)	0.92132 (11)	0.0190 (4)
C22	0.8556 (2)	0.2427 (2)	0.86003 (12)	0.0248 (5)
H22	0.8445	0.3351	0.8448	0.03*
C23	0.9191 (2)	0.1535 (3)	0.82173 (13)	0.0277 (5)
H23	0.9517	0.1852	0.78	0.033*
C24	0.9349 (2)	0.0194 (2)	0.84401 (12)	0.0259 (5)
H24	0.9779	−0.0407	0.8173	0.031*
C25	0.8888 (2)	−0.0286 (2)	0.90496 (12)	0.0279 (5)
H25	0.9006	−0.1211	0.92	0.033*
C26	0.82535 (19)	0.0586 (2)	0.94395 (11)	0.0234 (5)
H26	0.7937	0.0262	0.9858	0.028*
C31	0.58328 (19)	0.3633 (2)	0.89296 (12)	0.0190 (4)
C32	0.55896 (19)	0.4996 (2)	0.87323 (11)	0.0218 (4)
H32	0.6151	0.5684	0.8988	0.026*
C33	0.4516 (2)	0.5334 (2)	0.81564 (12)	0.0287 (5)
H33	0.4333	0.6259	0.8026	0.034*
C34	0.3712 (2)	0.4324 (3)	0.77727 (12)	0.0304 (5)
H34	0.2981	0.4565	0.7381	0.036*
C35	0.3962 (2)	0.2971 (3)	0.79540 (13)	0.0300 (5)
H35	0.3408	0.2287	0.7687	0.036*
C36	0.5029 (2)	0.2621 (2)	0.85284 (12)	0.0255 (5)
H36	0.5213	0.1693	0.865	0.031*
C41	0.67445 (19)	0.2279 (2)	1.04433 (11)	0.0192 (4)
C42	0.77158 (19)	0.1919 (2)	1.10755 (11)	0.0227 (5)
H42	0.8574	0.2166	1.1094	0.027*
C43	0.7430 (2)	0.1200 (2)	1.16796 (13)	0.0245 (5)
H43	0.8095	0.0927	1.2106	0.029*
C44	0.6173 (2)	0.0879 (2)	1.16600 (12)	0.0267 (5)
H44	0.5978	0.0394	1.2076	0.032*
C45	0.5194 (2)	0.1262 (2)	1.10375 (13)	0.0271 (5)
H45	0.4333	0.105	1.1032	0.033*
C46	0.54803 (19)	0.1959 (2)	1.04212 (12)	0.0220 (4)
H46	0.4818	0.2213	0.999	0.026*
Br	0.896182 (19)	0.62173 (2)	0.832770 (11)	0.02197 (11)
P	0.72110 (4)	0.31217 (5)	0.96590 (3)	0.01667 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0176 (10)	0.0259 (11)	0.0151 (9)	−0.0014 (8)	0.0019 (8)	0.0008 (8)
C12	0.0254 (11)	0.0297 (12)	0.0210 (11)	−0.0005 (9)	0.0059 (9)	−0.0048 (9)
C13	0.0376 (14)	0.0383 (15)	0.0626 (18)	−0.0100 (12)	0.0208 (13)	−0.0213 (13)
C21	0.0149 (9)	0.0245 (11)	0.0158 (10)	0.0009 (8)	−0.0001 (8)	−0.0015 (8)
C22	0.0267 (11)	0.0260 (12)	0.0226 (11)	0.0003 (9)	0.0080 (9)	0.0003 (9)
C23	0.0228 (11)	0.0360 (13)	0.0260 (12)	−0.0020 (10)	0.0093 (10)	−0.0033 (10)
C24	0.0171 (10)	0.0346 (13)	0.0231 (11)	0.0055 (9)	−0.0005 (9)	−0.0095 (9)
C25	0.0258 (11)	0.0266 (12)	0.0264 (11)	0.0045 (9)	−0.0031 (9)	−0.0035 (9)
C26	0.0232 (11)	0.0257 (11)	0.0187 (10)	0.0023 (9)	0.0000 (9)	0.0014 (9)
C31	0.0157 (10)	0.0269 (12)	0.0146 (10)	0.0019 (8)	0.0038 (8)	−0.0002 (8)
C32	0.0222 (10)	0.0262 (11)	0.0172 (10)	0.0029 (9)	0.0049 (8)	−0.0003 (9)
C33	0.0311 (12)	0.0356 (14)	0.0200 (11)	0.0125 (10)	0.0077 (10)	0.0061 (9)
C34	0.0201 (11)	0.0519 (15)	0.0171 (11)	0.0092 (11)	0.0001 (9)	0.0007 (11)
C35	0.0223 (11)	0.0439 (15)	0.0212 (11)	−0.0027 (10)	0.0000 (9)	−0.0078 (10)
C36	0.0236 (11)	0.0307 (12)	0.0208 (11)	−0.0001 (9)	0.0028 (9)	−0.0027 (9)
C41	0.0212 (10)	0.0221 (11)	0.0147 (10)	0.0017 (8)	0.0048 (8)	−0.0001 (8)
C42	0.0187 (10)	0.0299 (12)	0.0193 (10)	0.0006 (9)	0.0040 (8)	0.0016 (9)
C43	0.0256 (12)	0.0288 (13)	0.0179 (11)	0.0030 (9)	0.0029 (9)	0.0019 (8)
C44	0.0354 (13)	0.0263 (12)	0.0201 (12)	−0.0021 (10)	0.0102 (10)	0.0014 (9)
C45	0.0229 (12)	0.0314 (13)	0.0280 (12)	−0.0064 (9)	0.0081 (10)	0.0008 (9)
C46	0.0197 (10)	0.0258 (12)	0.0195 (10)	−0.0006 (9)	0.0027 (8)	−0.0007 (8)
Br	0.02320 (16)	0.02418 (17)	0.01761 (16)	−0.00167 (8)	0.00316 (11)	0.00069 (8)
P	0.0149 (3)	0.0211 (3)	0.0131 (3)	0.0010 (2)	0.0016 (2)	0.00138 (19)

Geometric parameters (Å, º)

C11—C12	1.541 (3)	C31—C36	1.400 (3)
C11—P	1.793 (2)	C31—P	1.797 (2)
C11—H11A	0.99	C32—C33	1.392 (3)
C11—H11B	0.99	C32—H32	0.95
C12—C13	1.521 (3)	C33—C34	1.387 (3)
C12—H12A	0.99	C33—H33	0.95
C12—H12B	0.99	C34—C35	1.383 (4)
C13—H13A	0.98	C34—H34	0.95
C13—H13B	0.98	C35—C36	1.388 (3)
C13—H13C	0.98	C35—H35	0.95
C21—C26	1.396 (3)	C36—H36	0.95
C21—C22	1.399 (3)	C41—C42	1.389 (3)
C21—P	1.7980 (19)	C41—C46	1.392 (3)
C22—C23	1.392 (3)	C41—P	1.8020 (19)
C22—H22	0.95	C42—C43	1.387 (3)
C23—C24	1.379 (3)	C42—H42	0.95
C23—H23	0.95	C43—C44	1.385 (3)
C24—C25	1.386 (3)	C43—H43	0.95
C24—H24	0.95	C44—C45	1.389 (3)
C25—C26	1.386 (3)	C44—H44	0.95
C25—H25	0.95	C45—C46	1.394 (3)
C26—H26	0.95	C45—H45	0.95
C31—C32	1.397 (3)	C46—H46	0.95
C12—C11—P	113.98 (13)	C33—C32—C31	119.3 (2)
C12—C11—H11A	108.8	C33—C32—H32	120.4
P—C11—H11A	108.8	C31—C32—H32	120.4
C12—C11—H11B	108.8	C34—C33—C32	120.2 (2)
P—C11—H11B	108.8	C34—C33—H33	119.9
H11A—C11—H11B	107.7	C32—C33—H33	119.9
C13—C12—C11	111.18 (17)	C35—C34—C33	120.8 (2)
C13—C12—H12A	109.4	C35—C34—H34	119.6
C11—C12—H12A	109.4	C33—C34—H34	119.6
C13—C12—H12B	109.4	C34—C35—C36	119.5 (2)
C11—C12—H12B	109.4	C34—C35—H35	120.2
H12A—C12—H12B	108	C36—C35—H35	120.2
C12—C13—H13A	109.5	C35—C36—C31	120.2 (2)
C12—C13—H13B	109.5	C35—C36—H36	119.9
H13A—C13—H13B	109.5	C31—C36—H36	119.9
C12—C13—H13C	109.5	C42—C41—C46	120.49 (18)
H13A—C13—H13C	109.5	C42—C41—P	116.91 (15)
H13B—C13—H13C	109.5	C46—C41—P	122.58 (15)
C26—C21—C22	120.40 (18)	C43—C42—C41	119.84 (19)
C26—C21—P	122.49 (14)	C43—C42—H42	120.1
C22—C21—P	117.07 (15)	C41—C42—H42	120.1
C23—C22—C21	119.0 (2)	C44—C43—C42	119.8 (2)
C23—C22—H22	120.5	C44—C43—H43	120.1
C21—C22—H22	120.5	C42—C43—H43	120.1
C24—C23—C22	120.3 (2)	C43—C44—C45	120.64 (19)
C24—C23—H23	119.9	C43—C44—H44	119.7
C22—C23—H23	119.9	C45—C44—H44	119.7
C23—C24—C25	120.76 (19)	C44—C45—C46	119.7 (2)
C23—C24—H24	119.6	C44—C45—H45	120.1
C25—C24—H24	119.6	C46—C45—H45	120.1
C24—C25—C26	119.9 (2)	C41—C46—C45	119.48 (19)
C24—C25—H25	120.1	C41—C46—H46	120.3
C26—C25—H25	120.1	C45—C46—H46	120.3
C25—C26—C21	119.62 (19)	C11—P—C31	110.52 (10)
C25—C26—H26	120.2	C11—P—C21	110.50 (9)
C21—C26—H26	120.2	C31—P—C21	106.86 (9)
C32—C31—C36	120.0 (2)	C11—P—C41	109.36 (9)
C32—C31—P	121.65 (16)	C31—P—C41	110.82 (9)
C36—C31—P	118.29 (16)	C21—P—C41	108.74 (9)
P—C11—C12—C13	−150.20 (17)	P—C41—C46—C45	177.66 (16)
C26—C21—C22—C23	0.4 (3)	C44—C45—C46—C41	−0.9 (3)
P—C21—C22—C23	−177.37 (17)	C12—C11—P—C31	72.36 (16)
C21—C22—C23—C24	0.0 (3)	C12—C11—P—C21	−169.57 (14)
C22—C23—C24—C25	−0.4 (3)	C12—C11—P—C41	−49.90 (17)
C23—C24—C25—C26	0.3 (3)	C32—C31—P—C11	−2.73 (19)
C24—C25—C26—C21	0.1 (3)	C36—C31—P—C11	174.01 (15)
C22—C21—C26—C25	−0.5 (3)	C32—C31—P—C21	−123.01 (16)
P—C21—C26—C25	177.17 (16)	C36—C31—P—C21	53.74 (17)
C36—C31—C32—C33	2.5 (3)	C32—C31—P—C41	118.67 (16)
P—C31—C32—C33	179.21 (14)	C36—C31—P—C41	−64.58 (17)
C31—C32—C33—C34	−1.3 (3)	C26—C21—P—C11	123.93 (17)
C32—C33—C34—C35	−0.1 (3)	C22—C21—P—C11	−58.36 (18)
C33—C34—C35—C36	0.2 (3)	C26—C21—P—C31	−115.77 (17)
C34—C35—C36—C31	1.1 (3)	C22—C21—P—C31	61.93 (18)
C32—C31—C36—C35	−2.4 (3)	C26—C21—P—C41	3.9 (2)
P—C31—C36—C35	−179.22 (16)	C22—C21—P—C41	−178.39 (15)
C46—C41—C42—C43	1.9 (3)	C42—C41—P—C11	−53.23 (18)
P—C41—C42—C43	−176.31 (15)	C46—C41—P—C11	128.55 (17)
C41—C42—C43—C44	−2.0 (3)	C42—C41—P—C31	−175.32 (16)
C42—C43—C44—C45	0.6 (3)	C46—C41—P—C31	6.5 (2)
C43—C44—C45—C46	0.9 (3)	C42—C41—P—C21	67.51 (18)
C42—C41—C46—C45	−0.5 (3)	C46—C41—P—C21	−110.72 (17)