[4-(Bromo­methyl)­benz­yl]triphenyl­phospho­nium bromide acetonitrile monosolvate

Burke, B.P.; Greenman, P.; Smith, A.M.; Archibald, S.J.

doi:10.1107/S1600536812042341

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3202

doi:10.1107/S1600536812042341

Open

access

[4-(Bromomethyl)benzyl]triphenylphosphonium bromide acetonitrile monosolvate

Benjamin P. Burke,^a Peter Greenman,^a Adam M. Smith ^a and Stephen J. Archibald ^a ^*

^aDepartment of Chemistry, University of Hull, Hull, HU6 7RX, UK
^*Correspondence e-mail: s.j.archibald@hull.ac.uk

(Received 4 October 2012; accepted 9 October 2012; online 24 October 2012)

In the title compound, C₂₆H₂₃BrP⁺·Br⁻·C₂H₃N, 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 molecule.

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_r = 567.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.051
S = 0.68
4473 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) -x, -y+2, -z; (ii) -x, -y+1, -z+1; (iii) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042341/rz5012sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812042341/rz5012Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812042341/rz5012Isup4.cml

checkCIF report

Comment top

Triphenylphosphonium cations are known to accumulate in cancer cell mitochondria due to a significant increase in mitochondrial transmembrane potential between normal epithelial cells and carcinoma cells, causing a potential tenfold higher accumulation of cationic compounds in carcinoma cells (Modica-Napolitano et al., 2001; Modica-Napolitano et al., 2002). Increase in uptake in myocardial cells also gives the potential for use as heart targeting agents (Kim et al., 2012). (4-Bromomethylbenzyl)triphenylphosphonium bromide has been used as a precursor to synthesize a ⁶⁴Cu radiolabelled molecule for potential cancer detection by positron emission tomography (Wang et al., 2007). Related compounds have also been radiolabelled with the ¹⁸F isotope (Kim et al., 2012; Madar et al., 2007).

In the cation of the title compound (Fig. 1), the dihedral angles formed by the C2–C7 benzene ring with the C9–C14, C15–C20 and C21–C26 phenyl rings are 34.04 (12), 45.48 (13) and 87.18 (9)°, respectively. In the crystal (Fig. 2), centrosymmetric pairs of ions are linked through C—H···Br hydrogen bonds (Table 1). The dimeric aggregates interact with the acetonitrile solvent molecules by C—H···N hydrogen bonds.

Related literature top

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). Scheme must show acetonitrile solvate

Experimental top

The synthetic procedure was completed following literature methods (Wang et al., 2007). Triphenylphosphine (2 g, 7.73 mmol) in toluene (25 ml) was added dropwise to a stirred solution of α,α-dibromo-p-xylene (2.01 g, 7.73 mmol) in toluene (25 ml). The mixture was heated under reflux for 18 h. The reaction was cooled to room temperature, filtered and washed with toluene (20 ml) and diethyl ether (20 ml) to as a white solid (3.35 g, 82%). ¹H-NMR (CDCl₃): δ 4.39 (s, 2H, CH₂—Br), 5.48 (d, 2H, CH₂—P, J = 14.7 Hz), 7.10 (s, 4H, CH—Ar), 7.61 (m, 6H, CH—Ar), 7.76 (m, 9H, CH—Ar). ¹³C-NMR (CDCl₃): δ 30.22 (CH₂—P), 30.68 (CH₂—P), 32.98 (CH₂—P), 117.35 (CH—Ar), 118.21 (CH—Ar), 127.75 (C—Ar), 127.83 (C—Ar), 129.48 (CH—Ar), 130.18 (CH—Ar), 130.30 (CH—Ar), 132.10 (CH—Ar), 134.56 (CH—Ar), 135.09 (CH—Ar), 138.17 (C—Ar). ³¹P-NMR (CDCl₃): δ 24.09 (s, PPh₃). The crystals were grown by vapour diffusion of diethyl ether into an acetonitrile solution of the title compound at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEP plot of the title compound using 50% probability ellipsoids with all non-H atoms labelled.
	Fig. 2. The packing in the unit cell with displacement ellipsoids drawn at the 50% probability level. Intermolecular hydrogen bonds are shown as dashed lines.

[4-(Bromomethyl)benzyl]triphenylphosphonium bromide acetonitrile monosolvate top

Crystal data top

C₂₆H₂₃BrP·Br·C₂H₃N	Z = 2
M_r = 567.29	F(000) = 572
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.069
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
rotation method scans	h = −11→11
Absorption correction: integration (X-AREA; Stoe & Cie, 2002)	k = −14→14
T_min = 0.336, T_max = 0.661	l = −14→14
9761 measured reflections

Refinement top

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(F_o²) + (0.006P)²] where P = (F_o² + 2F_c²)/3
4473 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₆H₂₃BrP·Br·C₂H₃N	γ = 69.293 (19)°
M_r = 567.29	V = 1272.4 (5) Å³
Triclinic, P1	Z = 2
a = 9.588 (2) Å	Mo Kα radiation
b = 12.333 (3) Å	µ = 3.26 mm⁻¹
c = 12.393 (3) Å	T = 150 K
α = 74.961 (19)°	0.2 × 0.2 × 0.1 mm
β = 70.051 (18)°

Data collection top

Stoe IPDSII diffractometer	4473 independent reflections
Absorption correction: integration (X-AREA; Stoe & Cie, 2002)	2659 reflections with I > 2σ(I)
T_min = 0.336, T_max = 0.661	R_int = 0.069
9761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 0.68	Δρ_max = 0.41 e Å⁻³
4473 reflections	Δρ_min = −0.36 e Å⁻³
290 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃BrP·Br·C₂H₃N
M_r	567.29
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.588 (2), 12.333 (3), 12.393 (3)
α, β, γ (°)	74.961 (19), 70.051 (18), 69.293 (19)
V (Å³)	1272.4 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.26
Crystal size (mm)	0.2 × 0.2 × 0.1

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-AREA; Stoe & Cie, 2002)
T_min, T_max	0.336, 0.661
No. of measured, independent and observed [I > 2σ(I)] reflections	9761, 4473, 2659
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.051, 0.68
No. of reflections	4473
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1ⁱ	0.99	2.60	3.488 (6)	149.6
C8—H8A···Br2ⁱⁱ	0.99	2.64	3.625 (4)	171.9
C8—H8B···Br2ⁱⁱⁱ	0.99	2.79	3.753 (3)	165.8
C20—H20···Br2ⁱⁱⁱ	0.95	2.81	3.746 (4)	168.7
C28—H28C···Br2	0.98	2.69	3.673 (5)	176.0

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) x, y+1, z.

Acknowledgements

We acknowledge the EPSRC for funds which enabled the purchase of the Stoe IPDSII diffractometer. We thank the University of Hull for the provision of a scholarship for BPB and the Nuffield Foundation for sponsorship of PG via the CREST programme. We acknowledge the use of the EPSRC's Chemical Database Service at Daresbury (Fletcher et al., 1996 ).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746–749. CrossRef CAS Web of Science Google Scholar
Kim, D.-Y., Kim, H.-J., Yu, K.-H. & Min, J.-J. (2012). Bioconj. Chem. 23, 431–437. Web of Science CrossRef CAS Google Scholar
Kim, Y.-S., Yang, C.-T., Wang, J., Wang, L., Li, Z.-B., Chen, X. & Liu, S. (2008). J. Med. Chem. 51, 2971–2984. Web of Science CrossRef PubMed CAS Google Scholar
Madar, I., Ravert, H., DiPaula, A., Du, Y., Dannals, R. F. & Becker, L. (2007). J. Nucl. Med. 48, 1021–1030. Web of Science CrossRef PubMed CAS Google Scholar
Modica-Napolitano, J. S. & Aprille, J. R. (2001). Adv. Drug. Del. Rev. 49, 63–70. CAS Google Scholar
Modica-Napolitano, J. S. & Singh, K. K. (2002). Exp. Rev. Mol. Med. 4, 1–19. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Wang, J., Yang, C.-T., Kim, Y.-S., Sreerama, S. G., Cao, Q., Li, Z.-B., He, Z., Chen, X. & Liu, S. (2007). J. Med. Chem. 50, 5057–5059. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3202

doi:10.1107/S1600536812042341

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[4-(Bromo­methyl)­benz­yl]tri­phenyl­phospho­nium bromide aceto­nitrile monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[4-(Bromomethyl)benzyl]triphenylphosphonium bromide acetonitrile monosolvate