(2-Hy­droxy­eth­yl)triphenyl­phospho­nium chloride

Ceylan, Ü.; Tanak, H.; Türkkan, E.; Dereli, Ö.; Büyükgüngör, O.

doi:10.1107/S160053681100482X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o641

doi:10.1107/S160053681100482X

Open

access

(2-Hydroxyethyl)triphenylphosphonium chloride

Ümit Ceylan,^a ^* Hasan Tanak,^b Ercan Türkkan,^c Ömer Dereli ^c and Orhan Büyükgüngör ^a

^aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey, ^bDepartment of Physics, Faculty of Arts & Science, Amasya University, TR-05100 Amasya, Turkey, and ^cDepartment of Physics, A. K. Education Faculty, Selcuk University, TR-42090 Meram–Konya, Turkey
^*Correspondence e-mail: uceylan@omu.edu.tr

(Received 23 January 2011; accepted 8 February 2011; online 16 February 2011)

In the crystal structure of the title compound, C₂₀H₂₀OP⁺·Cl⁻, the cations and anions are linked by intermolecular C—H⋯Cl and O—H⋯Cl hydrogen bonds into chains running parallel to the b axis. In the cation, the hydroxyethyl group is disordered over two orientations with site-occupancy factors of 0.554 (4) and 0.446 (4).

Related literature

For general background to the Wittig reaction, see: Wittig & Schöllkopf (1954 ); Wittig & Haag (1955 ). For the synthesis, applications and biological activity of triphenylphosphonium compounds, see: Rideout et al. (1989 ); Cooper et al. (2001 ); Dubios & Lin (1978 ); Lou & Shang (2000 ); Calderon et al. (2008 ). For related structures, see: Shafiq et al. (2008 ); Wu et al. (2007 ).

Experimental

Crystal data

C₂₀H₂₀OP⁺·Cl⁻
M_r = 342.78
Monoclinic, C 2/c
a = 14.1988 (4) Å
b = 12.5743 (3) Å
c = 19.7098 (6) Å
β = 92.510 (2)°
V = 3515.61 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.76 × 0.71 × 0.60 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.599, T_max = 0.905
26668 measured reflections
3725 independent reflections
3317 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.07
3725 reflections
230 parameters
35 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1	0.93	2.78	3.7009 (19)	171
C19—H19C⋯Cl1	0.97	2.73	3.6325 (18)	154
O1B—H1B⋯Cl1ⁱ	0.82	2.32	3.115 (4)	162
O1A—H1A⋯Cl1ⁱ	0.82	2.55	3.314 (4)	155
C19—H19B⋯Cl1ⁱ	0.97	2.78	3.5935 (19)	142
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100482X/rz2551sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100482X/rz2551Isup2.hkl

checkCIF report

Comment top

Triphenylphosphonium compounds and their various derivatives are key reagents in the Wittig reactions and are used to convert aldehydes and ketones into alkenes (Wittig & Schöllkopf, 1954; Wittig & Haag, 1955), specifically in applications ranging from the synthesis of simple alkenes to the construction of complex biologically active molecules in the pharmaceutical research (Rideout et al., 1989; Cooper et al., 2001). They are also an important class of isoaromatic compounds and have widespread applications for their antimicrobial and anticancer activities (Dubios & Lin, 1978; Lou & Shang, 2000). In addition, phosphonium compounds enhance flame retardancy mainly in textile industry (Calderon et al., 2008).

The title compound crystallizes with one cation and anion in the asymmetric unit (Fig. 1). In the molecule, the hydroxyethyl group (C19—C20—O1) is disordered over two orientations with site occupancy factors of 0.554 (4) and 0.446 (4), respectively. The dihedral angles between rings A (C1—C6), B (C7—C12) and C (C13—C18) are A/B = 73.79 (1)°, A/C = 67.88 (1)° and B/C = 70.96 (1)°. All the geometric parameters are in agreement with those observed in related compounds (Shafiq et al., 2008; Wu et al., 2007). The minimum separation between the P⁺ and Cl^- centres is 4.211 (1)Å. In the crystal structure, intermolecular C—H···Cl and C—H···O hydrogen bonds (Table 1) link the ions to form chains parallel to the b axis (Fig. 2).

Related literature top

For general background to the Wittig reaction, see: Wittig & Schöllkopf (1954); Wittig & Haag (1955). For the synthesis, applications and biological activity of triphenylphosphonium compounds, see: Rideout et al. (1989); Cooper et al. (2001); Dubios & Lin (1978); Lou & Shang (2000); Calderon et al. (2008). For related structures, see: Shafiq et al. (2008); Wu et al. (2007).

Experimental top

(2-Hydroxyethyl)triphenylphosphonium chloride powder was purchased from Merck. Single crystals suitable for X-ray ananlysis were grown by slow evaporation of a concentrated acetonitrile solution.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The structure of the title compound, with 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are drawn as dashed lines.

(2-Hydroxyethyl)triphenylphosphonium chloride top

Crystal data top

C₂₀H₂₀OP⁺·Cl⁻	F(000) = 1440
M_r = 342.78	D_x = 1.295 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 36925 reflections
a = 14.1988 (4) Å	θ = 2.1–27.3°
b = 12.5743 (3) Å	µ = 0.31 mm⁻¹
c = 19.7098 (6) Å	T = 296 K
β = 92.510 (2)°	Prism, colorless
V = 3515.61 (17) Å³	0.76 × 0.71 × 0.60 mm
Z = 8

Data collection top

Stoe IPDS 2 diffractometer	3725 independent reflections
Radiation source: fine-focus sealed tube	3317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 2.1°
rotation method scans	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
T_min = 0.599, T_max = 0.905	l = −24→24
26668 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0495P)² + 1.6584P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3725 reflections	Δρ_max = 0.42 e Å⁻³
230 parameters	Δρ_min = −0.24 e Å⁻³
35 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (6)

Crystal data top

C₂₀H₂₀OP⁺·Cl⁻	V = 3515.61 (17) Å³
M_r = 342.78	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.1988 (4) Å	µ = 0.31 mm⁻¹
b = 12.5743 (3) Å	T = 296 K
c = 19.7098 (6) Å	0.76 × 0.71 × 0.60 mm
β = 92.510 (2)°

Data collection top

Stoe IPDS 2 diffractometer	3725 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3317 reflections with I > 2σ(I)
T_min = 0.599, T_max = 0.905	R_int = 0.046
26668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	35 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
3725 reflections	Δρ_min = −0.24 e Å⁻³
230 parameters

Special details top

Experimental. 360 frames, detector distance = 120 mm

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	Occ. (<1)
Cl1	0.25807 (3)	0.74387 (4)	0.18184 (2)	0.06015 (16)
P1	0.22348 (3)	0.60936 (3)	0.37482 (2)	0.04301 (14)
C1	0.34518 (11)	0.64165 (12)	0.39231 (8)	0.0449 (3)
C2	0.39771 (12)	0.68183 (14)	0.33985 (9)	0.0545 (4)
H2	0.3690	0.6949	0.2973	0.065*
C3	0.49228 (13)	0.70205 (16)	0.35142 (11)	0.0633 (5)
H3	0.5273	0.7292	0.3166	0.076*
C4	0.53530 (13)	0.68242 (17)	0.41386 (11)	0.0655 (5)
H4	0.5994	0.6958	0.4210	0.079*
C5	0.48442 (14)	0.64332 (17)	0.46574 (10)	0.0652 (5)
H5	0.5140	0.6305	0.5080	0.078*
C6	0.38882 (12)	0.62269 (15)	0.45550 (9)	0.0543 (4)
H6	0.3542	0.5963	0.4908	0.065*
C7	0.18175 (11)	0.54012 (13)	0.44737 (8)	0.0457 (3)
C8	0.21070 (14)	0.43627 (15)	0.46028 (9)	0.0606 (5)
H8	0.2449	0.3994	0.4287	0.073*
C9	0.18823 (16)	0.38821 (15)	0.52053 (10)	0.0665 (5)
H9	0.2087	0.3193	0.5298	0.080*
C10	0.13605 (13)	0.44101 (16)	0.56677 (9)	0.0608 (5)
H10	0.1221	0.4082	0.6074	0.073*
C11	0.10449 (13)	0.54206 (17)	0.55326 (9)	0.0617 (5)
H11	0.0675	0.5769	0.5841	0.074*
C12	0.12762 (12)	0.59252 (14)	0.49368 (9)	0.0527 (4)
H12	0.1068	0.6615	0.4848	0.063*
C13	0.15396 (11)	0.72717 (13)	0.36117 (8)	0.0450 (3)
C14	0.05633 (12)	0.71654 (16)	0.34952 (10)	0.0581 (4)
H14	0.0288	0.6494	0.3490	0.070*
C15	0.00133 (13)	0.80521 (18)	0.33882 (10)	0.0667 (5)
H15	−0.0634	0.7980	0.3308	0.080*
C16	0.04150 (15)	0.90428 (17)	0.33992 (10)	0.0677 (5)
H16	0.0037	0.9640	0.3329	0.081*
C17	0.13779 (15)	0.91629 (15)	0.35143 (10)	0.0629 (5)
H17	0.1646	0.9838	0.3522	0.076*
C18	0.19394 (12)	0.82728 (13)	0.36184 (9)	0.0510 (4)
H18	0.2587	0.8349	0.3693	0.061*
C19	0.22152 (13)	0.52738 (14)	0.29984 (8)	0.0548 (4)
H19A	0.2554	0.5656	0.2658	0.066*	0.554 (4)
H19B	0.2580	0.4641	0.3111	0.066*	0.554 (4)
H19C	0.2453	0.5679	0.2624	0.066*	0.446 (4)
H19D	0.2628	0.4668	0.3078	0.066*	0.446 (4)
O1A	0.0805 (2)	0.4345 (3)	0.31380 (16)	0.0879 (10)	0.554 (4)
H1A	0.1117	0.3827	0.3265	0.132*	0.554 (4)
C20A	0.1293 (4)	0.4906 (5)	0.2660 (4)	0.0667 (14)	0.554 (4)
H20A	0.0926	0.5514	0.2500	0.080*	0.554 (4)
H20B	0.1414	0.4454	0.2275	0.080*	0.554 (4)
O1B	0.1262 (3)	0.4096 (3)	0.23172 (16)	0.0766 (11)	0.446 (4)
H1B	0.1513	0.3564	0.2483	0.115*	0.446 (4)
C20B	0.1230 (4)	0.4883 (6)	0.2807 (6)	0.0672 (17)	0.446 (4)
H20C	0.0940	0.4603	0.3206	0.081*	0.446 (4)
H20D	0.0848	0.5471	0.2634	0.081*	0.446 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0621 (3)	0.0621 (3)	0.0561 (3)	0.0009 (2)	0.0013 (2)	0.00363 (19)
P1	0.0439 (2)	0.0434 (2)	0.0418 (2)	−0.00118 (16)	0.00250 (15)	0.00225 (15)
C1	0.0427 (8)	0.0448 (8)	0.0472 (8)	0.0022 (6)	0.0027 (6)	−0.0008 (6)
C2	0.0510 (9)	0.0598 (10)	0.0529 (9)	−0.0018 (8)	0.0037 (7)	0.0069 (7)
C3	0.0509 (10)	0.0718 (12)	0.0680 (11)	−0.0066 (9)	0.0106 (8)	0.0017 (9)
C4	0.0458 (9)	0.0720 (12)	0.0784 (13)	−0.0019 (8)	0.0006 (9)	−0.0108 (10)
C5	0.0562 (10)	0.0778 (13)	0.0604 (11)	0.0042 (9)	−0.0114 (8)	−0.0055 (9)
C6	0.0543 (9)	0.0613 (10)	0.0471 (8)	0.0014 (8)	0.0019 (7)	−0.0021 (7)
C7	0.0487 (8)	0.0458 (8)	0.0426 (7)	−0.0049 (6)	0.0026 (6)	0.0010 (6)
C8	0.0772 (12)	0.0519 (10)	0.0536 (9)	0.0067 (9)	0.0128 (9)	0.0036 (8)
C9	0.0862 (14)	0.0535 (10)	0.0602 (11)	0.0025 (9)	0.0076 (10)	0.0128 (8)
C10	0.0636 (11)	0.0698 (12)	0.0495 (9)	−0.0113 (9)	0.0074 (8)	0.0110 (8)
C11	0.0621 (10)	0.0727 (12)	0.0513 (9)	−0.0048 (9)	0.0144 (8)	−0.0046 (8)
C12	0.0568 (9)	0.0496 (9)	0.0522 (9)	−0.0016 (7)	0.0067 (7)	−0.0014 (7)
C13	0.0438 (8)	0.0482 (8)	0.0432 (7)	0.0017 (6)	0.0033 (6)	0.0035 (6)
C14	0.0468 (9)	0.0621 (10)	0.0654 (11)	−0.0026 (8)	0.0017 (8)	0.0010 (8)
C15	0.0475 (10)	0.0838 (14)	0.0683 (12)	0.0128 (9)	−0.0026 (8)	−0.0017 (10)
C16	0.0713 (12)	0.0689 (12)	0.0626 (11)	0.0249 (10)	0.0007 (9)	0.0045 (9)
C17	0.0767 (13)	0.0480 (9)	0.0644 (11)	0.0044 (9)	0.0073 (9)	0.0040 (8)
C18	0.0495 (9)	0.0510 (9)	0.0528 (9)	−0.0004 (7)	0.0043 (7)	0.0021 (7)
C19	0.0666 (10)	0.0499 (9)	0.0476 (8)	−0.0022 (8)	0.0013 (7)	−0.0016 (7)
O1A	0.0844 (19)	0.087 (2)	0.091 (2)	−0.0292 (16)	−0.0075 (15)	0.0052 (17)
C20A	0.080 (2)	0.0603 (19)	0.058 (3)	−0.0002 (17)	−0.0162 (18)	−0.0101 (17)
O1B	0.086 (2)	0.075 (2)	0.067 (2)	−0.0013 (17)	−0.0132 (16)	−0.0231 (16)
C20B	0.073 (2)	0.064 (2)	0.063 (4)	0.003 (2)	−0.018 (2)	−0.014 (2)

Geometric parameters (Å, º) top

P1—C1	1.7938 (16)	C13—C18	1.381 (2)
P1—C13	1.7939 (16)	C13—C14	1.401 (2)
P1—C7	1.7968 (15)	C14—C15	1.372 (3)
P1—C19	1.8009 (17)	C14—H14	0.9300
C1—C6	1.387 (2)	C15—C16	1.370 (3)
C1—C2	1.396 (2)	C15—H15	0.9300
C2—C3	1.376 (2)	C16—C17	1.384 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.372 (3)	C17—C18	1.384 (2)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.369 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20A	1.515 (4)
C5—C6	1.388 (3)	C19—C20B	1.516 (4)
C5—H5	0.9300	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C12	1.385 (2)	C19—H19C	0.9700
C7—C8	1.389 (2)	C19—H19D	0.9700
C8—C9	1.382 (2)	O1A—C20A	1.386 (8)
C8—H8	0.9300	O1A—H1A	0.8200
C9—C10	1.371 (3)	C20A—H20A	0.9700
C9—H9	0.9300	C20A—H20B	0.9700
C10—C11	1.370 (3)	O1B—C20B	1.383 (8)
C10—H10	0.9300	O1B—H1B	0.8200
C11—C12	1.387 (2)	C20B—H20C	0.9700
C11—H11	0.9300	C20B—H20D	0.9700
C12—H12	0.9300

C1—P1—C13	111.16 (7)	C15—C14—H14	120.0
C1—P1—C7	107.77 (7)	C13—C14—H14	120.0
C13—P1—C7	108.73 (7)	C16—C15—C14	120.17 (18)
C1—P1—C19	105.51 (8)	C16—C15—H15	119.9
C13—P1—C19	111.16 (8)	C14—C15—H15	119.9
C7—P1—C19	112.45 (8)	C15—C16—C17	120.62 (18)
C6—C1—C2	119.68 (15)	C15—C16—H16	119.7
C6—C1—P1	121.49 (12)	C17—C16—H16	119.7
C2—C1—P1	118.76 (12)	C18—C17—C16	119.63 (18)
C3—C2—C1	119.56 (17)	C18—C17—H17	120.2
C3—C2—H2	120.2	C16—C17—H17	120.2
C1—C2—H2	120.2	C13—C18—C17	120.12 (16)
C4—C3—C2	120.56 (18)	C13—C18—H18	119.9
C4—C3—H3	119.7	C17—C18—H18	119.9
C2—C3—H3	119.7	C20A—C19—P1	121.2 (4)
C5—C4—C3	120.38 (18)	C20B—C19—P1	111.8 (4)
C5—C4—H4	119.8	C20A—C19—H19A	107.0
C3—C4—H4	119.8	C20B—C19—H19A	118.0
C4—C5—C6	120.22 (18)	P1—C19—H19A	107.0
C4—C5—H5	119.9	C20A—C19—H19B	107.0
C6—C5—H5	119.9	C20B—C19—H19B	105.6
C1—C6—C5	119.60 (17)	P1—C19—H19B	107.0
C1—C6—H6	120.2	H19A—C19—H19B	106.8
C5—C6—H6	120.2	C20A—C19—H19C	98.6
C12—C7—C8	119.65 (15)	C20B—C19—H19C	109.3
C12—C7—P1	120.38 (13)	P1—C19—H19C	109.3
C8—C7—P1	119.74 (12)	H19B—C19—H19C	113.9
C9—C8—C7	119.39 (17)	C20A—C19—H19D	109.6
C9—C8—H8	120.3	C20B—C19—H19D	109.3
C7—C8—H8	120.3	P1—C19—H19D	109.3
C10—C9—C8	120.75 (18)	H19A—C19—H19D	100.8
C10—C9—H9	119.6	H19C—C19—H19D	107.9
C8—C9—H9	119.6	O1A—C20A—C19	107.7 (5)
C11—C10—C9	120.12 (16)	O1A—C20A—H20A	110.2
C11—C10—H10	119.9	C19—C20A—H20A	110.2
C9—C10—H10	119.9	O1A—C20A—H20B	110.2
C10—C11—C12	120.10 (17)	C19—C20A—H20B	110.2
C10—C11—H11	120.0	H20A—C20A—H20B	108.5
C12—C11—H11	120.0	C20B—O1B—H1B	109.5
C7—C12—C11	119.94 (17)	O1B—C20B—C19	110.3 (6)
C7—C12—H12	120.0	O1B—C20B—H20C	109.6
C11—C12—H12	120.0	C19—C20B—H20C	109.6
C18—C13—C14	119.46 (16)	O1B—C20B—H20D	109.6
C18—C13—P1	121.88 (12)	C19—C20B—H20D	109.6
C14—C13—P1	118.66 (13)	H20C—C20B—H20D	108.1
C15—C14—C13	120.00 (18)

C13—P1—C1—C6	112.88 (14)	P1—C7—C12—C11	−172.90 (14)
C7—P1—C1—C6	−6.17 (16)	C10—C11—C12—C7	0.8 (3)
C19—P1—C1—C6	−126.51 (14)	C1—P1—C13—C18	2.53 (16)
C13—P1—C1—C2	−70.32 (15)	C7—P1—C13—C18	121.01 (14)
C7—P1—C1—C2	170.63 (13)	C19—P1—C13—C18	−114.68 (15)
C19—P1—C1—C2	50.29 (15)	C1—P1—C13—C14	−177.47 (13)
C6—C1—C2—C3	0.1 (3)	C7—P1—C13—C14	−58.99 (15)
P1—C1—C2—C3	−176.77 (14)	C19—P1—C13—C14	65.32 (15)
C1—C2—C3—C4	0.4 (3)	C18—C13—C14—C15	0.1 (3)
C2—C3—C4—C5	−0.6 (3)	P1—C13—C14—C15	−179.91 (15)
C3—C4—C5—C6	0.3 (3)	C13—C14—C15—C16	−0.4 (3)
C2—C1—C6—C5	−0.4 (3)	C14—C15—C16—C17	0.3 (3)
P1—C1—C6—C5	176.39 (14)	C15—C16—C17—C18	0.1 (3)
C4—C5—C6—C1	0.2 (3)	C14—C13—C18—C17	0.3 (2)
C1—P1—C7—C12	101.87 (14)	P1—C13—C18—C17	−179.67 (13)
C13—P1—C7—C12	−18.72 (16)	C16—C17—C18—C13	−0.4 (3)
C19—P1—C7—C12	−142.27 (14)	C1—P1—C19—C20A	−175.4 (3)
C1—P1—C7—C8	−72.50 (16)	C13—P1—C19—C20A	−54.8 (3)
C13—P1—C7—C8	166.91 (14)	C7—P1—C19—C20A	67.4 (3)
C19—P1—C7—C8	43.36 (17)	C1—P1—C19—C20B	176.9 (4)
C12—C7—C8—C9	−2.6 (3)	C13—P1—C19—C20B	−62.5 (4)
P1—C7—C8—C9	171.81 (16)	C7—P1—C19—C20B	59.6 (4)
C7—C8—C9—C10	1.5 (3)	C20B—C19—C20A—O1A	−20 (2)
C8—C9—C10—C11	0.8 (3)	P1—C19—C20A—O1A	−57.9 (5)
C9—C10—C11—C12	−2.0 (3)	C20A—C19—C20B—O1B	47 (2)
C8—C7—C12—C11	1.5 (3)	P1—C19—C20B—O1B	−168.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	0.93	2.78	3.7009 (19)	171
C19—H19C···Cl1	0.97	2.73	3.6325 (18)	154
O1B—H1B···Cl1ⁱ	0.82	2.32	3.115 (4)	162
O1A—H1A···Cl1ⁱ	0.82	2.55	3.314 (4)	155
C19—H19B···Cl1ⁱ	0.97	2.78	3.5935 (19)	142

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀OP⁺·Cl⁻
M_r	342.78
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	14.1988 (4), 12.5743 (3), 19.7098 (6)
β (°)	92.510 (2)
V (Å³)	3515.61 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.76 × 0.71 × 0.60

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.599, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	26668, 3725, 3317
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.07
No. of reflections	3725
No. of parameters	230
No. of restraints	35
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.24

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	0.93	2.78	3.7009 (19)	171
C19—H19C···Cl1	0.97	2.73	3.6325 (18)	154
O1B—H1B···Cl1ⁱ	0.82	2.32	3.115 (4)	162
O1A—H1A···Cl1ⁱ	0.82	2.55	3.314 (4)	155
C19—H19B···Cl1ⁱ	0.97	2.78	3.5935 (19)	142

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was financially supported by the BAP Selcuk University in Turkey. The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Calderon, J. U., Lennox, B. & Kamal, M. R. (2008). Appl. Clay. Sci. 40, 90–98. Web of Science CrossRef CAS Google Scholar
Cooper, W. A., Bartier, W. A., Rideout, D. C. & Delikatny, E. J. (2001). Magn. Reson. Med. 45, 1001–1010. Web of Science CrossRef PubMed CAS Google Scholar
Dubios, R. J. & Lin, C. C. L. (1978). J. Med. Chem. 21, 303–306. PubMed Web of Science Google Scholar
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
Lou, Z. W. & Shang, X. M. (2000). Chin. J. Med. Chem. 10, 168–171. CAS Google Scholar
Rideout, D., Calogeropoulou, T., Jaworski, J. S., Dagnino, R. & McCarthy, M. R. (1989). Anti-Cancer Drug Des. 4, 265–280. CAS PubMed Web of Science Google Scholar
Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Zaib-un-Nisa (2008). Acta Cryst. E64, o2213. 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-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Wittig, G. & Haag, W. (1955). Chem. Ber. 88, 1654–1666. CrossRef CAS Web of Science Google Scholar
Wittig, G. & Schöllkopf, U. (1954). Chem. Ber. 87, 1318–1330. CrossRef Web of Science Google Scholar
Wu, D.-Y., Li, F.-S., Xia, J.-Y., Mao, N.-W. & Yao, H.-L. (2007). Acta Cryst. E63, o4532. Web of Science CSD CrossRef IUCr Journals Google Scholar