[4-(Bromo-methyl)-benz-yl]triphenyl-phospho-nium bromide acetonitrile monosolvate.

In the title compound, C(26)H(23)BrP(+)·Br(-)·C(2)H(3)N, the dihedral angles between the plane of the benzylic phenyl ring attached to the P atom and the planes of the three directly attached phenyl rings are 34.04 (12), 45.48 (13) and 87.18 (9)°. In the crystal, centrosymmetric pairs of cations and anions are linked into dimeric aggregates via C-H⋯Br hydrogen bonds. There is also a C-H⋯N hydrogen bond to the acetonitrile solvent mol-ecule.

Related literature

For background to the biological activity of alkyl­triphenyl­phospho­nium derivatives, see: Modica-Napolitano & Aprille (2001 ▶); Modica-Napolitano & Singh (2002 ▶); Wang et al. (2007 ▶); Kim et al. (2008 ▶, 2012 ▶); Madar et al. (2007 ▶). For the synthesis of triphenyl­phospho­nium salts, see: Wang et al. (2007 ▶).

Experimental

Crystal data

C26H23BrP·Br·C2H3N

M = 567.29

Triclinic,

a = 9.588 (2) Å

b = 12.333 (3) Å

c = 12.393 (3) Å

α = 74.961 (19)°

β = 70.051 (18)°

γ = 69.293 (19)°

V = 1272.4 (5) Å3

Z = 2

Mo Kα radiation

μ = 3.26 mm−1

T = 150 K

0.2 × 0.2 × 0.1 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-AREA; Stoe & Cie, 2002 ▶) T min = 0.336, T max = 0.661

9761 measured reflections

4473 independent reflections

2659 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.051

S = 0.68

4473 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042341/rz5012sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042341/rz5012Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042341/rz5012Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042341/rz5012Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H23BrP·Br·C2H3N	Z = 2
Mr = 567.29	F(000) = 572
Triclinic, P1	Dx = 1.481 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.588 (2) Å	Cell parameters from 8439 reflections
b = 12.333 (3) Å	θ = 2.5–31.3°
c = 12.393 (3) Å	µ = 3.26 mm−1
α = 74.961 (19)°	T = 150 K
β = 70.051 (18)°	Block, colourless
γ = 69.293 (19)°	0.2 × 0.2 × 0.1 mm
V = 1272.4 (5) Å3

Stoe IPDSII diffractometer	4473 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2659 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.069
Detector resolution: 6.67 pixels mm-1	θmax = 25.0°, θmin = 2.5°
rotation method scans	h = −11→11
Absorption correction: integration (X-AREA; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.336, Tmax = 0.661	l = −14→14
9761 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H-atom parameters constrained
S = 0.68	w = 1/[σ2(Fo2) + (0.006P)2] where P = (Fo2 + 2Fc2)/3
4473 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	−0.52982 (5)	1.49983 (4)	0.20248 (4)	0.04070 (13)
P1	0.06715 (11)	0.85342 (8)	0.29654 (7)	0.0195 (2)
C1	−0.3828 (5)	1.3828 (3)	0.1005 (3)	0.0329 (9)
H1A	−0.4412	1.3555	0.0661	0.04*
H1B	−0.3108	1.4201	0.0363	0.04*
C2	−0.2931 (4)	1.2814 (3)	0.1680 (3)	0.0236 (8)
C3	−0.1400 (5)	1.2690 (3)	0.1579 (3)	0.0294 (9)
H3	−0.0933	1.3272	0.1085	0.035*
C4	−0.0535 (4)	1.1727 (3)	0.2190 (3)	0.0241 (8)
H4	0.0523	1.1643	0.2091	0.029*
C5	−0.1216 (4)	1.0885 (3)	0.2945 (3)	0.0218 (8)
C6	−0.2768 (4)	1.1031 (3)	0.3071 (3)	0.0217 (8)
H6	−0.3252	1.0469	0.3593	0.026*
C7	−0.3611 (4)	1.1972 (3)	0.2453 (3)	0.0251 (8)
H7	−0.4668	1.2053	0.2552	0.03*
C8	−0.0296 (4)	0.9850 (3)	0.3620 (3)	0.0227 (8)
H8A	−0.1004	0.9652	0.4387	0.027*
H8B	0.0498	1.0093	0.3762	0.027*
C9	0.2092 (4)	0.8782 (3)	0.1619 (3)	0.0204 (8)
C10	0.3660 (4)	0.8213 (3)	0.1497 (3)	0.0244 (8)
H10	0.3989	0.7697	0.2138	0.029*
C11	0.4742 (5)	0.8391 (3)	0.0450 (3)	0.0318 (9)
H11	0.5812	0.7988	0.0362	0.038*
C12	0.4249 (5)	0.9165 (3)	−0.0472 (3)	0.0302 (9)
H12	0.4989	0.9296	−0.1194	0.036*
C13	0.2709 (5)	0.9743 (3)	−0.0353 (3)	0.0309 (9)
H13	0.2387	1.0275	−0.099	0.037*
C14	0.1624 (4)	0.9557 (3)	0.0685 (3)	0.0244 (8)
H14	0.0555	0.9957	0.0763	0.029*
C15	0.1567 (4)	0.7414 (3)	0.3975 (3)	0.0198 (8)
C16	0.1466 (4)	0.6276 (3)	0.4163 (3)	0.0264 (9)
H16	0.0899	0.6102	0.3767	0.032*
C17	0.2181 (5)	0.5399 (3)	0.4921 (3)	0.0320 (9)
H17	0.2102	0.4627	0.5047	0.038*
C18	0.3018 (4)	0.5651 (3)	0.5497 (3)	0.0290 (9)
H18	0.3519	0.5049	0.6014	0.035*
C19	0.3122 (5)	0.6764 (3)	0.5322 (3)	0.0269 (9)
H19	0.3684	0.6931	0.5728	0.032*
C20	0.2417 (4)	0.7656 (3)	0.4559 (3)	0.0251 (8)
H20	0.251	0.8423	0.4435	0.03*
C21	−0.0684 (4)	0.8008 (3)	0.2692 (3)	0.0225 (8)
C22	−0.0205 (4)	0.7420 (3)	0.1738 (3)	0.0287 (9)
H22	0.0792	0.736	0.1202	0.034*
C23	−0.1217 (5)	0.6925 (3)	0.1590 (3)	0.0352 (10)
H23	−0.0903	0.6515	0.0955	0.042*
C24	−0.2656 (5)	0.7026 (3)	0.2355 (3)	0.0351 (10)
H24	−0.3341	0.6695	0.2239	0.042*
C25	−0.3130 (5)	0.7606 (3)	0.3295 (3)	0.0348 (10)
H25	−0.4137	0.7676	0.3817	0.042*
C26	−0.2129 (4)	0.8083 (3)	0.3474 (3)	0.0269 (9)
H26	−0.2438	0.846	0.4131	0.032*
N1	0.1911 (5)	0.4067 (4)	0.0535 (4)	0.0620 (12)
C27	0.1653 (5)	0.3903 (4)	0.1509 (4)	0.0397 (11)
C28	0.1253 (6)	0.3696 (4)	0.2764 (4)	0.0597 (14)
H28A	0.0123	0.3888	0.3079	0.089*
H28B	0.1638	0.419	0.3028	0.089*
H28C	0.1726	0.2868	0.3037	0.089*
Br2	0.31729 (5)	0.05853 (4)	0.36399 (3)	0.03526 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.0414 (3)	0.0292 (3)	0.0486 (3)	0.0017 (2)	−0.0175 (2)	−0.0113 (2)
P1	0.0172 (5)	0.0218 (5)	0.0185 (5)	−0.0050 (4)	−0.0032 (4)	−0.0050 (4)
C1	0.039 (3)	0.031 (2)	0.024 (2)	−0.006 (2)	−0.0057 (18)	−0.0067 (17)
C2	0.025 (2)	0.022 (2)	0.0220 (18)	−0.0026 (18)	−0.0049 (16)	−0.0094 (16)
C3	0.038 (3)	0.027 (2)	0.025 (2)	−0.017 (2)	−0.0027 (18)	−0.0034 (17)
C4	0.017 (2)	0.030 (2)	0.0236 (19)	−0.0083 (18)	0.0004 (15)	−0.0063 (17)
C5	0.023 (2)	0.018 (2)	0.0249 (19)	−0.0045 (17)	−0.0050 (16)	−0.0086 (15)
C6	0.024 (2)	0.019 (2)	0.0227 (18)	−0.0099 (17)	−0.0035 (16)	−0.0041 (15)
C7	0.022 (2)	0.021 (2)	0.032 (2)	−0.0027 (18)	−0.0074 (17)	−0.0092 (17)
C8	0.025 (2)	0.021 (2)	0.0215 (18)	−0.0082 (18)	−0.0031 (16)	−0.0049 (16)
C9	0.018 (2)	0.023 (2)	0.0218 (18)	−0.0050 (17)	−0.0056 (15)	−0.0085 (15)
C10	0.021 (2)	0.027 (2)	0.0236 (19)	−0.0053 (17)	−0.0071 (16)	−0.0015 (16)
C11	0.022 (2)	0.038 (3)	0.033 (2)	−0.0071 (19)	−0.0012 (17)	−0.0119 (19)
C12	0.035 (3)	0.036 (2)	0.0193 (19)	−0.017 (2)	0.0005 (17)	−0.0064 (17)
C13	0.042 (3)	0.030 (2)	0.0192 (19)	−0.010 (2)	−0.0091 (18)	−0.0004 (17)
C14	0.020 (2)	0.030 (2)	0.0204 (18)	−0.0045 (18)	−0.0034 (16)	−0.0068 (16)
C15	0.017 (2)	0.021 (2)	0.0167 (17)	−0.0030 (16)	0.0007 (14)	−0.0062 (14)
C16	0.027 (2)	0.030 (2)	0.0215 (19)	−0.0077 (19)	−0.0064 (17)	−0.0056 (16)
C17	0.037 (3)	0.021 (2)	0.035 (2)	−0.007 (2)	−0.0100 (19)	−0.0015 (18)
C18	0.022 (2)	0.028 (2)	0.0245 (19)	0.0061 (18)	−0.0072 (17)	−0.0014 (17)
C19	0.022 (2)	0.032 (2)	0.024 (2)	−0.0021 (18)	−0.0066 (17)	−0.0071 (17)
C20	0.026 (2)	0.023 (2)	0.0250 (19)	−0.0064 (18)	−0.0065 (16)	−0.0043 (16)
C21	0.023 (2)	0.023 (2)	0.0210 (18)	−0.0058 (17)	−0.0085 (16)	−0.0008 (15)
C22	0.029 (2)	0.034 (2)	0.0248 (19)	−0.0103 (19)	−0.0040 (17)	−0.0099 (17)
C23	0.046 (3)	0.037 (3)	0.032 (2)	−0.017 (2)	−0.016 (2)	−0.0062 (19)
C24	0.034 (3)	0.031 (3)	0.046 (3)	−0.013 (2)	−0.021 (2)	0.002 (2)
C25	0.025 (2)	0.033 (2)	0.046 (2)	−0.013 (2)	−0.0068 (19)	−0.004 (2)
C26	0.024 (2)	0.022 (2)	0.031 (2)	−0.0029 (18)	−0.0049 (17)	−0.0075 (17)
N1	0.060 (3)	0.072 (3)	0.065 (3)	−0.033 (3)	−0.010 (2)	−0.020 (2)
C27	0.033 (3)	0.039 (3)	0.051 (3)	−0.016 (2)	−0.002 (2)	−0.020 (2)
C28	0.065 (4)	0.063 (4)	0.053 (3)	−0.026 (3)	−0.003 (3)	−0.021 (3)
Br2	0.0345 (3)	0.0474 (3)	0.0261 (2)	−0.0247 (2)	0.00201 (18)	−0.0056 (2)

Br1—C1	1.990 (4)	C13—H13	0.95
P1—C15	1.791 (3)	C14—H14	0.95
P1—C9	1.792 (3)	C15—C16	1.394 (4)
P1—C21	1.800 (3)	C15—C20	1.401 (4)
P1—C8	1.805 (3)	C16—C17	1.382 (5)
C1—C2	1.480 (5)	C16—H16	0.95
C1—H1A	0.99	C17—C18	1.391 (5)
C1—H1B	0.99	C17—H17	0.95
C2—C3	1.386 (5)	C18—C19	1.367 (5)
C2—C7	1.400 (5)	C18—H18	0.95
C3—C4	1.392 (5)	C19—C20	1.390 (5)
C3—H3	0.95	C19—H19	0.95
C4—C5	1.392 (5)	C20—H20	0.95
C4—H4	0.95	C21—C26	1.381 (5)
C5—C6	1.393 (5)	C21—C22	1.405 (4)
C5—C8	1.504 (5)	C22—C23	1.394 (5)
C6—C7	1.373 (5)	C22—H22	0.95
C6—H6	0.95	C23—C24	1.366 (5)
C7—H7	0.95	C23—H23	0.95
C8—H8A	0.99	C24—C25	1.384 (5)
C8—H8B	0.99	C24—H24	0.95
C9—C10	1.389 (5)	C25—C26	1.388 (5)
C9—C14	1.390 (4)	C25—H25	0.95
C10—C11	1.379 (5)	C26—H26	0.95
C10—H10	0.95	N1—C27	1.123 (5)
C11—C12	1.387 (5)	C27—C28	1.446 (6)
C11—H11	0.95	C28—H28A	0.98
C12—C13	1.369 (5)	C28—H28B	0.98
C12—H12	0.95	C28—H28C	0.98
C13—C14	1.375 (5)
C15—P1—C9	110.46 (16)	C12—C13—H13	119.9
C15—P1—C21	107.13 (16)	C14—C13—H13	119.9
C9—P1—C21	108.45 (15)	C13—C14—C9	120.0 (4)
C15—P1—C8	108.01 (14)	C13—C14—H14	120
C9—P1—C8	111.25 (16)	C9—C14—H14	120
C21—P1—C8	111.47 (17)	C16—C15—C20	119.0 (3)
C2—C1—Br1	110.4 (2)	C16—C15—P1	120.2 (2)
C2—C1—H1A	109.6	C20—C15—P1	120.7 (3)
Br1—C1—H1A	109.6	C17—C16—C15	120.7 (3)
C2—C1—H1B	109.6	C17—C16—H16	119.6
Br1—C1—H1B	109.6	C15—C16—H16	119.6
H1A—C1—H1B	108.1	C16—C17—C18	119.7 (3)
C3—C2—C7	118.2 (3)	C16—C17—H17	120.2
C3—C2—C1	120.6 (3)	C18—C17—H17	120.2
C7—C2—C1	121.2 (3)	C19—C18—C17	120.1 (3)
C2—C3—C4	121.1 (3)	C19—C18—H18	119.9
C2—C3—H3	119.5	C17—C18—H18	119.9
C4—C3—H3	119.5	C18—C19—C20	121.0 (3)
C3—C4—C5	120.2 (3)	C18—C19—H19	119.5
C3—C4—H4	119.9	C20—C19—H19	119.5
C5—C4—H4	119.9	C19—C20—C15	119.5 (3)
C4—C5—C6	118.6 (3)	C19—C20—H20	120.3
C4—C5—C8	120.5 (3)	C15—C20—H20	120.3
C6—C5—C8	120.9 (3)	C26—C21—C22	120.3 (3)
C7—C6—C5	121.0 (3)	C26—C21—P1	120.1 (3)
C7—C6—H6	119.5	C22—C21—P1	119.3 (3)
C5—C6—H6	119.5	C23—C22—C21	118.9 (3)
C6—C7—C2	120.8 (3)	C23—C22—H22	120.5
C6—C7—H7	119.6	C21—C22—H22	120.5
C2—C7—H7	119.6	C24—C23—C22	120.3 (3)
C5—C8—P1	116.8 (2)	C24—C23—H23	119.9
C5—C8—H8A	108.1	C22—C23—H23	119.9
P1—C8—H8A	108.1	C23—C24—C25	120.9 (3)
C5—C8—H8B	108.1	C23—C24—H24	119.6
P1—C8—H8B	108.1	C25—C24—H24	119.6
H8A—C8—H8B	107.3	C24—C25—C26	119.9 (4)
C10—C9—C14	119.4 (3)	C24—C25—H25	120.1
C10—C9—P1	120.8 (3)	C26—C25—H25	120.1
C14—C9—P1	119.8 (3)	C21—C26—C25	119.7 (3)
C11—C10—C9	120.4 (3)	C21—C26—H26	120.1
C11—C10—H10	119.8	C25—C26—H26	120.1
C9—C10—H10	119.8	N1—C27—C28	177.5 (5)
C10—C11—C12	119.2 (4)	C27—C28—H28A	109.5
C10—C11—H11	120.4	C27—C28—H28B	109.5
C12—C11—H11	120.4	H28A—C28—H28B	109.5
C13—C12—C11	120.7 (4)	C27—C28—H28C	109.5
C13—C12—H12	119.6	H28A—C28—H28C	109.5
C11—C12—H12	119.6	H28B—C28—H28C	109.5
C12—C13—C14	120.3 (3)
Br1—C1—C2—C3	−104.0 (3)	P1—C9—C14—C13	−179.5 (2)
Br1—C1—C2—C7	74.5 (3)	C9—P1—C15—C16	−101.6 (3)
C7—C2—C3—C4	2.8 (5)	C21—P1—C15—C16	16.3 (3)
C1—C2—C3—C4	−178.6 (3)	C8—P1—C15—C16	136.5 (3)
C2—C3—C4—C5	−2.0 (5)	C9—P1—C15—C20	76.4 (3)
C3—C4—C5—C6	0.1 (5)	C21—P1—C15—C20	−165.6 (3)
C3—C4—C5—C8	−179.2 (3)	C8—P1—C15—C20	−45.4 (3)
C4—C5—C6—C7	1.0 (5)	C20—C15—C16—C17	0.5 (5)
C8—C5—C6—C7	−179.7 (3)	P1—C15—C16—C17	178.6 (3)
C5—C6—C7—C2	−0.1 (5)	C15—C16—C17—C18	−0.3 (6)
C3—C2—C7—C6	−1.8 (5)	C16—C17—C18—C19	0.5 (6)
C1—C2—C7—C6	179.7 (3)	C17—C18—C19—C20	−0.9 (6)
C4—C5—C8—P1	−92.4 (3)	C18—C19—C20—C15	1.0 (6)
C6—C5—C8—P1	88.4 (4)	C16—C15—C20—C19	−0.8 (5)
C15—P1—C8—C5	−176.2 (3)	P1—C15—C20—C19	−178.9 (3)
C9—P1—C8—C5	62.4 (3)	C15—P1—C21—C26	80.5 (3)
C21—P1—C8—C5	−58.8 (3)	C9—P1—C21—C26	−160.3 (3)
C15—P1—C9—C10	−5.0 (3)	C8—P1—C21—C26	−37.5 (3)
C21—P1—C9—C10	−122.1 (3)	C15—P1—C21—C22	−93.5 (3)
C8—P1—C9—C10	114.9 (3)	C9—P1—C21—C22	25.8 (3)
C15—P1—C9—C14	175.2 (3)	C8—P1—C21—C22	148.6 (3)
C21—P1—C9—C14	58.1 (3)	C26—C21—C22—C23	0.6 (5)
C8—P1—C9—C14	−64.9 (3)	P1—C21—C22—C23	174.5 (3)
C14—C9—C10—C11	−1.5 (5)	C21—C22—C23—C24	0.9 (6)
P1—C9—C10—C11	178.7 (2)	C22—C23—C24—C25	−0.9 (6)
C9—C10—C11—C12	1.4 (5)	C23—C24—C25—C26	−0.5 (6)
C10—C11—C12—C13	−0.4 (5)	C22—C21—C26—C25	−1.9 (6)
C11—C12—C13—C14	−0.4 (5)	P1—C21—C26—C25	−175.8 (3)
C12—C13—C14—C9	0.3 (5)	C24—C25—C26—C21	1.9 (6)
C10—C9—C14—C13	0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1i	0.99	2.60	3.488 (6)	150
C8—H8A···Br2ii	0.99	2.64	3.625 (4)	172
C8—H8B···Br2iii	0.99	2.79	3.753 (3)	166
C20—H20···Br2iii	0.95	2.81	3.746 (4)	169
C28—H28C···Br2	0.98	2.69	3.673 (5)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N1i	0.99	2.60	3.488 (6)	150
C8—H8A⋯Br2ii	0.99	2.64	3.625 (4)	172
C8—H8B⋯Br2iii	0.99	2.79	3.753 (3)	166
C20—H20⋯Br2iii	0.95	2.81	3.746 (4)	169
C28—H28C⋯Br2	0.98	2.69	3.673 (5)	176

Symmetry codes: (i) ; (ii) ; (iii) .