Iso­butyl­tri­phenyl­phospho­nium bromide

At 102 K, the iso­butyl group of the title compound, C₂₂H₂₄P⁺·Br^-, is in the extended conformation. However, the iso­propyl moiety is in the eclipsed conformation with respect to the H atoms on the C atom attached to the P atom. The benzene 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) = 0.004 Å
• R factor = 0.039
• wR factor = 0.112
• Data-to-parameter ratio = 16.4

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 (Farrugia, 1999).

(I)

Crystal data

C22H24P^+·Br^−	F(000) = 824
Mr = 399.29	Dx = 1.406 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 19309 reflections
a = 11.3309 (3) Å	θ = 4.1–70.1°
b = 9.8033 (2) Å	µ = 3.75 mm^−1
c = 17.7075 (3) Å	T = 102 K
β = 106.487 (1)°	Prism, colorless
V = 1886.08 (7) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker AXS diffractometer	3555 independent reflections
Radiation source: rotating anode	2997 reflections with I > 2σ(I)
Göbel focusing mirrors monochromator	Rint = 0.089
Detector resolution: 17 pixels mm^-1	θmax = 70.3°, θmin = 4.1°
ω scans	h = −13→11
Absorption correction: multi-scan (Blessing, 1995)	k = −11→11
Tmin = 0.37, Tmax = 0.685	l = −21→21
18578 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0659P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max = 0.035
S = 1.13	Δρmax = 0.67 e Å^−3
3555 reflections	Δρmin = −0.68 e Å^−3
217 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	0.3226 (2)	0.0231 (3)	0.50574 (14)	0.0244 (6)
H11A	0.3367	−0.0274	0.4607	0.029*
H11B	0.4038	0.0545	0.5389	0.029*
C12	0.2696 (2)	−0.0774 (3)	0.55456 (15)	0.0268 (6)
H12	0.1796	−0.0587	0.5442	0.032*
C13	0.3319 (3)	−0.0594 (3)	0.64243 (15)	0.0311 (6)
H13A	0.3212	0.0348	0.6577	0.047*
H13B	0.4199	−0.0797	0.6537	0.047*
H13C	0.2946	−0.1219	0.6723	0.047*
C14	0.2857 (3)	−0.2251 (3)	0.52971 (17)	0.0329 (7)
H14A	0.245	−0.2359	0.4733	0.049*
H14B	0.2488	−0.288	0.5596	0.049*
H14C	0.3736	−0.2456	0.5404	0.049*
C21	0.3164 (2)	0.2860 (3)	0.42381 (14)	0.0230 (6)
C22	0.3618 (2)	0.2355 (3)	0.36369 (15)	0.0280 (6)
H22	0.352	0.1419	0.3494	0.034*
C23	0.4215 (3)	0.3235 (3)	0.32487 (16)	0.0300 (6)
H23	0.4537	0.2898	0.2844	0.036*
C24	0.4340 (2)	0.4604 (3)	0.34519 (15)	0.0298 (6)
H24	0.4731	0.5205	0.3177	0.036*
C25	0.3903 (2)	0.5103 (3)	0.40515 (15)	0.0314 (7)
H25	0.4011	0.6038	0.4196	0.038*
C26	0.3306 (2)	0.4241 (3)	0.44414 (15)	0.0270 (6)
H26	0.2993	0.4586	0.4847	0.032*
C31	0.0959 (2)	0.1255 (3)	0.39074 (15)	0.0219 (6)
C32	0.0611 (2)	−0.0097 (3)	0.37388 (15)	0.0280 (6)
H32	0.1082	−0.0812	0.4042	0.034*
C33	−0.0431 (2)	−0.0396 (3)	0.31233 (16)	0.0321 (7)
H33	−0.0679	−0.1317	0.301	0.038*
C34	−0.1102 (2)	0.0642 (3)	0.26789 (15)	0.0324 (7)
H34	−0.1809	0.0431	0.2257	0.039*
C35	−0.0758 (2)	0.1995 (3)	0.28406 (17)	0.0330 (7)
H35	−0.1228	0.2707	0.2533	0.04*
C36	0.0270 (2)	0.2294 (3)	0.34516 (16)	0.0298 (6)
H36	0.0512	0.3217	0.3563	0.036*
C41	0.1883 (2)	0.2622 (3)	0.54405 (14)	0.0223 (5)
C42	0.2834 (2)	0.3073 (3)	0.60889 (15)	0.0265 (6)
H42	0.3664	0.2824	0.6141	0.032*
C43	0.2545 (3)	0.3886 (3)	0.66515 (16)	0.0297 (6)
H43	0.3186	0.4216	0.7084	0.036*
C44	0.1341 (3)	0.4222 (3)	0.65936 (16)	0.0313 (7)
H44	0.1157	0.4778	0.6984	0.038*
C45	0.0401 (3)	0.3747 (3)	0.59645 (18)	0.0335 (7)
H45	−0.043	0.3962	0.593	0.04*
C46	0.0673 (2)	0.2954 (3)	0.53823 (16)	0.0275 (6)
H46	0.0029	0.2642	0.4946	0.033*
Br	0.62321 (2)	0.14750 (3)	0.671491 (15)	0.02752 (14)
P	0.23154 (6)	0.17055 (7)	0.46802 (4)	0.02026 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0264 (13)	0.0216 (14)	0.0251 (12)	0.0022 (11)	0.0071 (11)	0.0004 (11)
C12	0.0266 (13)	0.0211 (15)	0.0330 (14)	0.0001 (11)	0.0090 (11)	0.0023 (12)
C13	0.0362 (14)	0.0265 (16)	0.0313 (14)	−0.0022 (12)	0.0109 (12)	0.0012 (12)
C14	0.0415 (16)	0.0200 (16)	0.0350 (15)	−0.0023 (12)	0.0074 (13)	0.0029 (12)
C21	0.0236 (12)	0.0202 (14)	0.0242 (12)	−0.0016 (10)	0.0049 (10)	0.0001 (11)
C22	0.0334 (14)	0.0188 (14)	0.0325 (14)	−0.0006 (11)	0.0104 (12)	0.0019 (12)
C23	0.0328 (14)	0.0302 (17)	0.0295 (14)	0.0020 (12)	0.0129 (12)	0.0043 (12)
C24	0.0286 (14)	0.0307 (17)	0.0273 (13)	−0.0047 (12)	0.0030 (11)	0.0076 (13)
C25	0.0347 (15)	0.0225 (15)	0.0321 (14)	−0.0028 (12)	0.0017 (12)	0.0028 (12)
C26	0.0307 (14)	0.0211 (15)	0.0283 (13)	−0.0015 (11)	0.0069 (11)	−0.0018 (12)
C31	0.0204 (12)	0.0223 (14)	0.0224 (12)	−0.0034 (10)	0.0051 (10)	−0.0029 (11)
C32	0.0316 (14)	0.0245 (16)	0.0267 (13)	0.0012 (11)	0.0065 (11)	0.0005 (12)
C33	0.0328 (14)	0.0291 (17)	0.0334 (15)	−0.0060 (12)	0.0079 (12)	−0.0061 (13)
C34	0.0236 (13)	0.045 (2)	0.0266 (13)	−0.0057 (12)	0.0036 (11)	−0.0030 (13)
C35	0.0297 (14)	0.0337 (18)	0.0318 (15)	0.0009 (13)	0.0027 (12)	0.0068 (13)
C36	0.0311 (14)	0.0226 (16)	0.0338 (14)	0.0009 (11)	0.0063 (12)	0.0046 (13)
C41	0.0296 (13)	0.0135 (13)	0.0251 (12)	0.0009 (10)	0.0101 (11)	−0.0012 (11)
C42	0.0298 (13)	0.0221 (15)	0.0276 (13)	−0.0013 (11)	0.0079 (11)	−0.0017 (12)
C43	0.0381 (15)	0.0249 (15)	0.0254 (13)	−0.0028 (12)	0.0081 (12)	−0.0057 (12)
C44	0.0474 (17)	0.0202 (16)	0.0307 (14)	0.0018 (12)	0.0182 (13)	−0.0028 (12)
C45	0.0332 (15)	0.0304 (16)	0.0409 (16)	0.0040 (12)	0.0167 (13)	−0.0020 (14)
C46	0.0294 (13)	0.0237 (15)	0.0296 (14)	−0.0021 (11)	0.0086 (11)	−0.0001 (12)
Br	0.0328 (2)	0.0190 (2)	0.0298 (2)	−0.00069 (10)	0.00723 (14)	0.00004 (11)
P	0.0224 (3)	0.0154 (4)	0.0223 (3)	−0.0005 (2)	0.0052 (3)	−0.0010 (3)

Geometric parameters (Å, º)

C11—C12	1.541 (4)	C31—C32	1.391 (4)
C11—P	1.791 (3)	C31—C36	1.393 (4)
C11—H11A	0.99	C31—P	1.799 (2)
C11—H11B	0.99	C32—C33	1.392 (4)
C12—C13	1.526 (3)	C32—H32	0.95
C12—C14	1.539 (4)	C33—C34	1.376 (4)
C12—H12	1	C33—H33	0.95
C13—H13A	0.98	C34—C35	1.389 (4)
C13—H13B	0.98	C34—H34	0.95
C13—H13C	0.98	C35—C36	1.378 (4)
C14—H14A	0.98	C35—H35	0.95
C14—H14B	0.98	C36—H36	0.95
C14—H14C	0.98	C41—C46	1.384 (4)
C21—C22	1.398 (4)	C41—C42	1.404 (4)
C21—C26	1.398 (4)	C41—P	1.798 (3)
C21—P	1.801 (3)	C42—C43	1.385 (4)
C22—C23	1.392 (4)	C42—H42	0.95
C22—H22	0.95	C43—C44	1.379 (4)
C23—C24	1.386 (4)	C43—H43	0.95
C23—H23	0.95	C44—C45	1.385 (4)
C24—C25	1.382 (4)	C44—H44	0.95
C24—H24	0.95	C45—C46	1.394 (4)
C25—C26	1.383 (4)	C45—H45	0.95
C25—H25	0.95	C46—H46	0.95
C26—H26	0.95
C12—C11—P	116.77 (18)	C32—C31—C36	119.6 (2)
C12—C11—H11A	108.1	C32—C31—P	121.77 (19)
P—C11—H11A	108.1	C36—C31—P	118.6 (2)
C12—C11—H11B	108.1	C31—C32—C33	119.7 (3)
P—C11—H11B	108.1	C31—C32—H32	120.2
H11A—C11—H11B	107.3	C33—C32—H32	120.2
C13—C12—C14	110.0 (2)	C34—C33—C32	120.0 (3)
C13—C12—C11	110.9 (2)	C34—C33—H33	120
C14—C12—C11	110.2 (2)	C32—C33—H33	120
C13—C12—H12	108.6	C33—C34—C35	120.7 (2)
C14—C12—H12	108.6	C33—C34—H34	119.6
C11—C12—H12	108.6	C35—C34—H34	119.6
C12—C13—H13A	109.5	C36—C35—C34	119.4 (3)
C12—C13—H13B	109.5	C36—C35—H35	120.3
H13A—C13—H13B	109.5	C34—C35—H35	120.3
C12—C13—H13C	109.5	C35—C36—C31	120.6 (3)
H13A—C13—H13C	109.5	C35—C36—H36	119.7
H13B—C13—H13C	109.5	C31—C36—H36	119.7
C12—C14—H14A	109.5	C46—C41—C42	120.1 (2)
C12—C14—H14B	109.5	C46—C41—P	122.40 (19)
H14A—C14—H14B	109.5	C42—C41—P	117.4 (2)
C12—C14—H14C	109.5	C43—C42—C41	119.1 (3)
H14A—C14—H14C	109.5	C43—C42—H42	120.5
H14B—C14—H14C	109.5	C41—C42—H42	120.5
C22—C21—C26	119.9 (2)	C44—C43—C42	121.0 (2)
C22—C21—P	117.8 (2)	C44—C43—H43	119.5
C26—C21—P	122.20 (19)	C42—C43—H43	119.5
C23—C22—C21	119.5 (3)	C43—C44—C45	119.9 (3)
C23—C22—H22	120.3	C43—C44—H44	120.1
C21—C22—H22	120.3	C45—C44—H44	120.1
C24—C23—C22	120.0 (3)	C44—C45—C46	120.1 (3)
C24—C23—H23	120	C44—C45—H45	120
C22—C23—H23	120	C46—C45—H45	120
C25—C24—C23	120.6 (3)	C41—C46—C45	119.9 (2)
C25—C24—H24	119.7	C41—C46—H46	120.1
C23—C24—H24	119.7	C45—C46—H46	120.1
C24—C25—C26	120.0 (3)	C11—P—C41	112.00 (12)
C24—C25—H25	120	C11—P—C31	111.26 (12)
C26—C25—H25	120	C41—P—C31	109.71 (12)
C25—C26—C21	120.0 (3)	C11—P—C21	110.30 (12)
C25—C26—H26	120	C41—P—C21	107.68 (12)
C21—C26—H26	120	C31—P—C21	105.65 (12)
P—C11—C12—C13	−102.2 (2)	P—C41—C46—C45	−175.6 (2)
P—C11—C12—C14	135.71 (19)	C44—C45—C46—C41	1.1 (4)
C26—C21—C22—C23	0.4 (4)	C12—C11—P—C41	52.7 (2)
P—C21—C22—C23	176.2 (2)	C12—C11—P—C31	−70.5 (2)
C21—C22—C23—C24	−0.9 (4)	C12—C11—P—C21	172.64 (18)
C22—C23—C24—C25	1.5 (4)	C46—C41—P—C11	−126.9 (2)
C23—C24—C25—C26	−1.6 (4)	C42—C41—P—C11	56.8 (2)
C24—C25—C26—C21	1.1 (4)	C46—C41—P—C31	−2.8 (3)
C22—C21—C26—C25	−0.5 (4)	C42—C41—P—C31	−179.1 (2)
P—C21—C26—C25	−176.11 (19)	C46—C41—P—C21	111.7 (2)
C36—C31—C32—C33	−0.8 (4)	C42—C41—P—C21	−64.6 (2)
P—C31—C32—C33	−178.6 (2)	C32—C31—P—C11	9.5 (3)
C31—C32—C33—C34	0.8 (4)	C36—C31—P—C11	−168.3 (2)
C32—C33—C34—C35	−0.5 (4)	C32—C31—P—C41	−115.0 (2)
C33—C34—C35—C36	0.3 (4)	C36—C31—P—C41	67.2 (2)
C34—C35—C36—C31	−0.3 (4)	C32—C31—P—C21	129.2 (2)
C32—C31—C36—C35	0.6 (4)	C36—C31—P—C21	−48.6 (3)
P—C31—C36—C35	178.4 (2)	C22—C21—P—C11	56.3 (2)
C46—C41—C42—C43	−2.0 (4)	C26—C21—P—C11	−128.0 (2)
P—C41—C42—C43	174.3 (2)	C22—C21—P—C41	178.76 (19)
C41—C42—C43—C44	1.8 (4)	C26—C21—P—C41	−5.5 (2)
C42—C43—C44—C45	−0.1 (4)	C22—C21—P—C31	−64.1 (2)
C43—C44—C45—C46	−1.3 (4)	C26—C21—P—C31	111.7 (2)
C42—C41—C46—C45	0.6 (4)