(3-Chloro­prop­yl)triphenyl­phospho­nium bromide

Kavitha, C.N.; Yathirajan, H.S.; Dayananda, A.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812042122

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3115

doi:10.1107/S1600536812042122

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(3-Chloropropyl)triphenylphosphonium bromide

Channappa N. Kavitha,^a Hemmige S. Yathirajan,^a A. S. Dayananda,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 4 October 2012; accepted 8 October 2012; online 13 October 2012)

The title compound, C₂₁H₂₁ClP⁺Br⁻, is the bromide salt of a mixed aryl-alkyl phosphonium cation. C–P–C angles span a range of 107.20 (10)–111.18 (10)°. The non-H atoms of the 3-chloropropyl 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 supramolecular layer lying parallel to (10-1) by C—H⋯π interactions.

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_r = 419.71
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.107
S = 1.06
4690 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.69 e Å⁻³
Δρ_min = −0.64 e Å⁻³

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) -x, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042122/tk5158sup1.cif

Supporting information file. DOI: 10.1107/S1600536812042122/tk5158Isup2.cdx

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

Supporting information file. DOI: 10.1107/S1600536812042122/tk5158Isup4.cml

checkCIF report

Comment top

Phosphonium salts are widely used in organic synthesis for the preparation of alkenes (Maercker, 1965; Carruthers, 1971) and are formed by alkylation of triaryl or trialkyl phosphines. Reports on (cycloalkylidenemethyl)triphenylphosphonium salts being used as versatile intermediate reagents have been published (Minami et al., 1988). The crystal structures of several mixed alkyl-aryl phosphonium bromides have been reported such as (3-cyanopropyl)triphenylphosphonium bromide (Czerwinski & Ponnuswamy, 1988a) and (3-bromopropyl)triphenylphosphonium bromide (Czerwinski & Ponnuswamy, 1988b).

The phosphorus atom is coordinated tetrahedrally. The C–P–C angles span a range of 107.20 (10)–111.18 (10)° with the smallest angle found in between two phenyl groups and the largest angle in between a phenyl and the 3-chloropropyl group. The non-hydrogen atoms of the 3-chloropropyl group adopt a staggered conformation, the corresponding C–C–C–Cl angle is found at -72.0 (3)° (Fig. 1).

In the crystal, two C–H···Br contacts whose range falls by more than 0.1 Å below the sum of van der Waals radii of the corresponding atoms are observed. These are supported by a hydrogen atom of a phenyl group as well as a hydrogen atom of the methylene group directly bonded to the phosphorus atom. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is DD on the unary level. Furthermore, a C–H···π contact stemming from one of the H atoms on a phenyl group is observed. Taking into account only the contacts that involve the bromide ion, the entities of the title compound are connected to a double zigzag chain along the crystallographic b axis. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 4.8882 (16) Å and is apparent between one of the phenyl groups and its symmetry-generated equivalent (Fig. 2).

The packing of the title compound in the crystal is shown in Figure 3.

Related literature top

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 top

The title compound was obtained as a gift sample from R. L. Fine Chem., Bengaluru, India. The compound was recrystallized from methanol by slow evaporation at room temperature and was used as such for diffraction studies.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. C–H···Br contacts, viewed along [-1 0 0]. Symmetry operators: ⁱ -x, -y + 1, -z; ⁱⁱ x, -y + 3/2, z - 1/2.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

(3-Chloropropyl)triphenylphosphonium bromide top

Crystal data top

C₂₁H₂₁ClP⁺·Br⁻	F(000) = 856
M_r = 419.71	D_x = 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0596P)² + 2.6325P] where P = (F_o² + 2F_c²)/3
4690 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 1.69 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₂₁H₂₁ClP⁺·Br⁻	V = 1887.70 (7) Å³
M_r = 419.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0708 (2) Å	µ = 2.40 mm⁻¹
b = 10.0435 (2) Å	T = 200 K
c = 17.5740 (4) Å	0.51 × 0.35 × 0.16 mm
β = 104.973 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4690 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4202 reflections with I > 2σ(I)
T_min = 0.324, T_max = 0.694	R_int = 0.014
18046 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	Δρ_max = 1.69 e Å⁻³
4690 reflections	Δρ_min = −0.64 e Å⁻³
217 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁ClP⁺·Br⁻
M_r	419.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	11.0708 (2), 10.0435 (2), 17.5740 (4)
β (°)	104.973 (1)
V (Å³)	1887.70 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.40
Crystal size (mm)	0.51 × 0.35 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.324, 0.694
No. of measured, independent and observed [I > 2σ(I)] reflections	18046, 4690, 4202
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.107, 1.06
No. of reflections	4690
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.69, −0.64

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

CNK thanks the University of Mysore for research facilities. HSY is grateful to R. L. Fine Chem., Bengaluru, India, for the gift sample of the title compound.

References

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