(2-Hy-droxy-eth-yl)triphenyl-phospho-nium chloride.

In the crystal structure of the title compound, C(20)H(20)OP(+)·Cl(-), the cations and anions are linked by inter-molecular C-H⋯Cl and O-H⋯Cl hydrogen bonds into chains running parallel to the b axis. In the cation, the hy-droxy-ethyl 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 = 342.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.07

3725 reflections

230 parameters

35 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

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

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

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

C20H20OP+·Cl−	F(000) = 1440
Mr = 342.78	Dx = 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

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

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(Fo2) + (0.0495P)2 + 1.6584P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3725 reflections	Δρmax = 0.42 e Å−3
230 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .