(3-Chloro-prop-yl)triphenyl-phospho-nium bromide.

The title compound, C(21)H(21)ClP(+)Br(-), is the bromide salt of a mixed aryl-alkyl phospho-nium cation. C-P-C angles span a range of 107.20 (10)-111.18 (10)°. The non-H atoms of the 3-chloro-propyl group adopt a staggered conformation [C-C-C-Cl torsion angle: -72.0 (3)°]. In the crystal, C-H⋯Br contacts connect the entities of the title compound into a double zigzag chain along b. These chains are linked into a supra-molecular layer lying parallel to (10-1) by C-H⋯π inter-actions.

Related literature

For synthetic applications of phospho­nium salts in organic chemistry, see: Maercker (1965 ▶); Carruthers (1971 ▶); Minami et al. (1988 ▶). For related structures, see: Czerwinski & Ponnuswamy (1988a ▶,b ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H21ClP+·Br−

M = 419.71

Monoclinic,

a = 11.0708 (2) Å

b = 10.0435 (2) Å

c = 17.5740 (4) Å

β = 104.973 (1)°

V = 1887.70 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.40 mm−1

T = 200 K

0.51 × 0.35 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.324, T max = 0.694

18046 measured reflections

4690 independent reflections

4202 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.107

S = 1.06

4690 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.69 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042122/tk5158sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042122/tk5158Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042122/tk5158Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042122/tk5158Isup4.cml

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

C21H21ClP+·Br−	F(000) = 856
Mr = 419.71	Dx = 1.477 Mg m−3
Monoclinic, P21/c	Melting point: 498 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0708 (2) Å	Cell parameters from 9926 reflections
b = 10.0435 (2) Å	θ = 2.4–28.3°
c = 17.5740 (4) Å	µ = 2.40 mm−1
β = 104.973 (1)°	T = 200 K
V = 1887.70 (7) Å3	Block, colourless
Z = 4	0.51 × 0.35 × 0.16 mm

Bruker APEXII CCD diffractometer	4690 independent reflections
Radiation source: fine-focus sealed tube	4202 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.324, Tmax = 0.694	k = −12→13
18046 measured reflections	l = −23→23

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0596P)2 + 2.6325P] where P = (Fo2 + 2Fc2)/3
4690 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 1.69 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.11226 (2)	0.37223 (2)	0.168258 (14)	0.02748 (9)
Cl1	0.19533 (8)	0.23552 (6)	−0.03470 (4)	0.03790 (17)
P1	0.27583 (5)	0.69448 (6)	0.03725 (3)	0.01760 (12)
C1	0.1762 (2)	0.5615 (2)	−0.01109 (13)	0.0210 (4)
H1A	0.1693	0.4937	0.0284	0.025*
H1B	0.0914	0.5972	−0.0347	0.025*
C2	0.2259 (2)	0.4953 (3)	−0.07590 (14)	0.0264 (5)
H2A	0.2184	0.5587	−0.1200	0.032*
H2B	0.3157	0.4743	−0.0545	0.032*
C3	0.1561 (3)	0.3691 (3)	−0.10672 (16)	0.0309 (5)
H3A	0.1774	0.3415	−0.1558	0.037*
H3B	0.0650	0.3862	−0.1195	0.037*
C11	0.4085 (2)	0.6285 (2)	0.10851 (13)	0.0204 (4)
C12	0.4923 (2)	0.7181 (3)	0.15544 (15)	0.0292 (5)
H12	0.4798	0.8112	0.1477	0.035*
C13	0.5936 (3)	0.6713 (3)	0.21322 (17)	0.0354 (6)
H13	0.6509	0.7321	0.2449	0.043*
C14	0.6108 (2)	0.5356 (3)	0.22457 (15)	0.0351 (6)
H14	0.6800	0.5034	0.2644	0.042*
C15	0.5282 (3)	0.4463 (3)	0.17839 (16)	0.0324 (6)
H15	0.5410	0.3533	0.1866	0.039*
C16	0.4263 (2)	0.4921 (2)	0.12005 (14)	0.0251 (5)
H16	0.3695	0.4308	0.0884	0.030*
C21	0.3235 (2)	0.7892 (2)	−0.03666 (13)	0.0209 (4)
C22	0.4486 (2)	0.8127 (3)	−0.03397 (15)	0.0272 (5)
H22	0.5130	0.7795	0.0085	0.033*
C23	0.4780 (3)	0.8854 (3)	−0.09427 (18)	0.0349 (6)
H23	0.5630	0.9006	−0.0935	0.042*
C24	0.3837 (3)	0.9355 (3)	−0.15517 (16)	0.0344 (6)
H24	0.4046	0.9861	−0.1957	0.041*
C25	0.2597 (3)	0.9131 (3)	−0.15792 (15)	0.0329 (6)
H25	0.1957	0.9484	−0.1999	0.039*
C26	0.2288 (2)	0.8389 (3)	−0.09917 (15)	0.0284 (5)
H26	0.1436	0.8218	−0.1013	0.034*
C31	0.1948 (2)	0.8024 (2)	0.08894 (13)	0.0199 (4)
C32	0.1688 (2)	0.9347 (2)	0.06715 (15)	0.0267 (5)
H32	0.1929	0.9704	0.0232	0.032*
C33	0.1073 (3)	1.0143 (3)	0.10998 (16)	0.0318 (5)
H33	0.0901	1.1049	0.0958	0.038*
C34	0.0712 (2)	0.9608 (3)	0.17351 (16)	0.0305 (5)
H34	0.0285	1.0151	0.2024	0.037*
C35	0.0965 (2)	0.8299 (3)	0.19506 (15)	0.0295 (5)
H35	0.0710	0.7944	0.2385	0.035*
C36	0.1593 (2)	0.7495 (2)	0.15347 (14)	0.0256 (5)
H36	0.1779	0.6595	0.1687	0.031*

	U11	U22	U33	U12	U13	U23
Br1	0.03111 (15)	0.02528 (14)	0.02542 (14)	0.00090 (9)	0.00617 (10)	−0.00151 (9)
Cl1	0.0561 (4)	0.0166 (3)	0.0364 (3)	−0.0049 (3)	0.0036 (3)	0.0049 (2)
P1	0.0175 (3)	0.0176 (3)	0.0169 (2)	−0.0003 (2)	0.00315 (19)	0.00100 (19)
C1	0.0201 (10)	0.0225 (11)	0.0196 (10)	−0.0031 (8)	0.0036 (8)	−0.0018 (8)
C2	0.0300 (12)	0.0267 (12)	0.0235 (11)	−0.0052 (10)	0.0090 (9)	−0.0035 (9)
C3	0.0325 (13)	0.0294 (13)	0.0291 (12)	−0.0046 (10)	0.0049 (10)	−0.0065 (10)
C11	0.0181 (10)	0.0239 (11)	0.0183 (10)	0.0016 (8)	0.0031 (8)	0.0008 (8)
C12	0.0278 (12)	0.0275 (12)	0.0288 (12)	−0.0031 (10)	0.0011 (10)	−0.0035 (10)
C13	0.0231 (12)	0.0500 (17)	0.0289 (13)	−0.0046 (12)	−0.0011 (10)	−0.0062 (12)
C14	0.0239 (12)	0.0552 (18)	0.0240 (11)	0.0134 (12)	0.0022 (9)	0.0040 (12)
C15	0.0348 (13)	0.0334 (13)	0.0285 (12)	0.0127 (11)	0.0074 (10)	0.0064 (10)
C16	0.0276 (11)	0.0246 (11)	0.0227 (11)	0.0028 (9)	0.0057 (9)	0.0016 (9)
C21	0.0229 (10)	0.0202 (10)	0.0203 (10)	−0.0016 (8)	0.0066 (8)	0.0016 (8)
C22	0.0247 (12)	0.0294 (12)	0.0278 (12)	−0.0042 (9)	0.0073 (9)	0.0000 (10)
C23	0.0334 (14)	0.0371 (14)	0.0381 (14)	−0.0124 (11)	0.0165 (12)	−0.0004 (11)
C24	0.0520 (17)	0.0277 (13)	0.0283 (12)	−0.0093 (12)	0.0191 (12)	0.0004 (10)
C25	0.0438 (15)	0.0317 (13)	0.0233 (11)	0.0032 (12)	0.0092 (11)	0.0059 (10)
C26	0.0279 (12)	0.0344 (13)	0.0232 (11)	0.0016 (10)	0.0072 (9)	0.0057 (10)
C31	0.0191 (10)	0.0197 (10)	0.0202 (10)	0.0001 (8)	0.0039 (8)	−0.0022 (8)
C32	0.0310 (12)	0.0228 (11)	0.0254 (11)	0.0034 (9)	0.0056 (9)	0.0023 (9)
C33	0.0332 (13)	0.0245 (12)	0.0350 (13)	0.0070 (10)	0.0037 (11)	−0.0022 (10)
C34	0.0210 (11)	0.0377 (14)	0.0311 (12)	0.0040 (10)	0.0033 (9)	−0.0111 (11)
C35	0.0264 (12)	0.0379 (14)	0.0264 (12)	−0.0042 (10)	0.0108 (9)	−0.0048 (10)
C36	0.0277 (12)	0.0236 (11)	0.0267 (11)	−0.0017 (9)	0.0092 (9)	0.0009 (9)

Cl1—C3	1.818 (3)	C16—H16	0.9500
P1—C11	1.793 (2)	C21—C22	1.393 (3)
P1—C21	1.796 (2)	C21—C26	1.400 (3)
P1—C31	1.796 (2)	C22—C23	1.393 (4)
P1—C1	1.799 (2)	C22—H22	0.9500
C1—C2	1.539 (3)	C23—C24	1.383 (4)
C1—H1A	0.9900	C23—H23	0.9500
C1—H1B	0.9900	C24—C25	1.380 (4)
C2—C3	1.511 (3)	C24—H24	0.9500
C2—H2A	0.9900	C25—C26	1.386 (4)
C2—H2B	0.9900	C25—H25	0.9500
C3—H3A	0.9900	C26—H26	0.9500
C3—H3B	0.9900	C31—C32	1.392 (3)
C11—C16	1.392 (3)	C31—C36	1.398 (3)
C11—C12	1.398 (3)	C32—C33	1.391 (4)
C12—C13	1.386 (4)	C32—H32	0.9500
C12—H12	0.9500	C33—C34	1.388 (4)
C13—C14	1.384 (5)	C33—H33	0.9500
C13—H13	0.9500	C34—C35	1.377 (4)
C14—C15	1.384 (4)	C34—H34	0.9500
C14—H14	0.9500	C35—C36	1.390 (4)
C15—C16	1.392 (3)	C35—H35	0.9500
C15—H15	0.9500	C36—H36	0.9500
C11—P1—C21	111.13 (11)	C11—C16—C15	119.3 (2)
C11—P1—C31	107.20 (10)	C11—C16—H16	120.3
C21—P1—C31	108.92 (11)	C15—C16—H16	120.3
C11—P1—C1	110.32 (11)	C22—C21—C26	120.2 (2)
C21—P1—C1	108.10 (11)	C22—C21—P1	122.69 (18)
C31—P1—C1	111.18 (10)	C26—C21—P1	117.13 (18)
C2—C1—P1	112.15 (16)	C21—C22—C23	119.3 (2)
C2—C1—H1A	109.2	C21—C22—H22	120.4
P1—C1—H1A	109.2	C23—C22—H22	120.4
C2—C1—H1B	109.2	C24—C23—C22	120.1 (3)
P1—C1—H1B	109.2	C24—C23—H23	120.0
H1A—C1—H1B	107.9	C22—C23—H23	120.0
C3—C2—C1	112.3 (2)	C25—C24—C23	120.9 (2)
C3—C2—H2A	109.1	C25—C24—H24	119.6
C1—C2—H2A	109.1	C23—C24—H24	119.6
C3—C2—H2B	109.1	C24—C25—C26	119.8 (3)
C1—C2—H2B	109.1	C24—C25—H25	120.1
H2A—C2—H2B	107.9	C26—C25—H25	120.1
C2—C3—Cl1	111.20 (18)	C25—C26—C21	119.8 (2)
C2—C3—H3A	109.4	C25—C26—H26	120.1
Cl1—C3—H3A	109.4	C21—C26—H26	120.1
C2—C3—H3B	109.4	C32—C31—C36	120.3 (2)
Cl1—C3—H3B	109.4	C32—C31—P1	122.14 (18)
H3A—C3—H3B	108.0	C36—C31—P1	117.55 (18)
C16—C11—C12	120.0 (2)	C33—C32—C31	119.7 (2)
C16—C11—P1	121.69 (18)	C33—C32—H32	120.2
C12—C11—P1	118.23 (18)	C31—C32—H32	120.2
C13—C12—C11	120.1 (3)	C34—C33—C32	119.7 (2)
C13—C12—H12	119.9	C34—C33—H33	120.1
C11—C12—H12	119.9	C32—C33—H33	120.1
C14—C13—C12	119.7 (3)	C35—C34—C33	120.7 (2)
C14—C13—H13	120.2	C35—C34—H34	119.7
C12—C13—H13	120.2	C33—C34—H34	119.7
C13—C14—C15	120.5 (2)	C34—C35—C36	120.3 (2)
C13—C14—H14	119.7	C34—C35—H35	119.9
C15—C14—H14	119.7	C36—C35—H35	119.9
C14—C15—C16	120.3 (3)	C35—C36—C31	119.3 (2)
C14—C15—H15	119.8	C35—C36—H36	120.4
C16—C15—H15	119.8	C31—C36—H36	120.4
C11—P1—C1—C2	−79.46 (19)	C1—P1—C21—C26	54.5 (2)
C21—P1—C1—C2	42.2 (2)	C26—C21—C22—C23	−0.3 (4)
C31—P1—C1—C2	161.75 (16)	P1—C21—C22—C23	179.0 (2)
P1—C1—C2—C3	169.87 (18)	C21—C22—C23—C24	1.2 (4)
C1—C2—C3—Cl1	−72.0 (3)	C22—C23—C24—C25	−0.9 (4)
C21—P1—C11—C16	−118.7 (2)	C23—C24—C25—C26	−0.3 (4)
C31—P1—C11—C16	122.4 (2)	C24—C25—C26—C21	1.2 (4)
C1—P1—C11—C16	1.2 (2)	C22—C21—C26—C25	−0.9 (4)
C21—P1—C11—C12	64.1 (2)	P1—C21—C26—C25	179.8 (2)
C31—P1—C11—C12	−54.8 (2)	C11—P1—C31—C32	124.8 (2)
C1—P1—C11—C12	−176.03 (19)	C21—P1—C31—C32	4.5 (2)
C16—C11—C12—C13	0.4 (4)	C1—P1—C31—C32	−114.5 (2)
P1—C11—C12—C13	177.7 (2)	C11—P1—C31—C36	−54.4 (2)
C11—C12—C13—C14	−0.4 (4)	C21—P1—C31—C36	−174.73 (18)
C12—C13—C14—C15	0.4 (4)	C1—P1—C31—C36	66.2 (2)
C13—C14—C15—C16	−0.2 (4)	C36—C31—C32—C33	0.1 (4)
C12—C11—C16—C15	−0.2 (4)	P1—C31—C32—C33	−179.1 (2)
P1—C11—C16—C15	−177.39 (19)	C31—C32—C33—C34	−0.7 (4)
C14—C15—C16—C11	0.1 (4)	C32—C33—C34—C35	0.5 (4)
C11—P1—C21—C22	−3.6 (2)	C33—C34—C35—C36	0.3 (4)
C31—P1—C21—C22	114.3 (2)	C34—C35—C36—C31	−0.9 (4)
C1—P1—C21—C22	−124.8 (2)	C32—C31—C36—C35	0.7 (4)
C11—P1—C21—C26	175.69 (19)	P1—C31—C36—C35	179.96 (19)
C31—P1—C21—C26	−66.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Br1i	0.99	2.82	3.703 (2)	149
C25—H25···Br1ii	0.95	2.89	3.751 (3)	151
C14—H14···Cg1iii	0.95	2.68	3.623 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯Br1i	0.99	2.82	3.703 (2)	149
C25—H25⋯Br1ii	0.95	2.89	3.751 (3)	151
C14—H14⋯Cg1iii	0.95	2.68	3.623 (3)	173

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