Crystal structure of (3-carb­oxy­prop­yl)tri­phenyl­phospho­nium hexa­fluorido­phosphate

Hillesheim, P.C.; Scipione, K.A.; Stokes, S.L.

doi:10.1107/S160053681402323X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1197-o1198

doi:10.1107/S160053681402323X

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Crystal structure of (3-carboxypropyl)triphenylphosphonium hexafluoridophosphate

Patrick C. Hillesheim,^a ^* Kent A. Scipione ^a and Sean L. Stokes ^a

^aMississippi State University, Department of Chemistry, 1115 Hand Lab, Box 9573, Mississippi State, MS 39762, USA
^*Correspondence e-mail: pch110@msstate.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 October 2014; accepted 21 October 2014; online 24 October 2014)

In the title molecular salt, C₂₂H₂₂O₂P⁺·PF₆⁻, the side chain of the cation adopts an anti–gauche conformation [P—C—C—C and C—C—C—C torsion angles = −179.11 (10) and −77.18 (16)°, respectively]. In the crystal, the cations are linked into carboxylic acid inversion dimers by pairs of O—H⋯O hydrogen bonds. Weak C—H⋯F and C—H⋯(F,F) hydrogen bonds connect the components into a three-dimensional network, but there are no aromatic π–π stacking interactions.

Keywords: crystal structure; phosphonium salt; hydrogen bonding.

CCDC reference: 1030392

1. Related literature

For structures of related compounds, see: Li & Mak (1996 ); Wu et al. (2007 ). For compounds containing related metallated structures, see: Li & Mak (1997 ); Sabounchei et al. (2011 ). For the use of phosphonium compounds as Wittig reagents, see: Hoffman (2001 ), as biocodal agents, see: Kanazawa et al. (1993 ) and as phase transfer agents, see: Starks (1971 ).

2. Experimental

2.1. Crystal data

C₂₂H₂₂O₂P⁺·PF₆⁻
M_r = 494.33
Triclinic, $[P \overline 1]$
a = 9.3307 (1) Å
b = 10.6773 (2) Å
c = 12.8129 (2) Å
α = 72.460 (1)°
β = 82.307 (1)°
γ = 65.495 (1)°
V = 1107.46 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.29 × 0.16 × 0.07 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.865, T_max = 0.947
37843 measured reflections
5269 independent reflections
4426 reflections with I > 2σ(I)
R_int = 0.035

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.087
S = 1.06
5269 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.42 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
O1—H1⋯O2ⁱ	0.84	1.80	2.6285 (15)	171
C1—H1A⋯F2	0.99	2.48	3.455 (2)	168
C1—H1A⋯F3	0.99	2.50	3.1656 (19)	124
C22—H22⋯F4ⁱⁱ	0.95	2.51	3.3924 (18)	155
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013 ); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1030392

Crystal structure: contains datablock I. DOI: 10.1107/S160053681402323X/hb7304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681402323X/hb7304Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681402323X/hb7304Isup3.mol

checkCIF report

Synthesis and crystallization top

A 1.0g (2.3mmol) sample of 3-carboxypropyltriphenylphosphonium chloride and 0.4g (2.4mmol) of sodium hexafluorophosphate were dissolved in 40mL of water. A white precipitate immediately formed and the slurry was stirred for 1 hour. The mixture was filtered, the solid was washed with water (3 x 25mL), and dried under high vacuum to yield a white solid. Yield: 0.65g (80.8%). Single crystals suitable for X-ray diffraction were grown from slow evaporation of dichloromethane. ¹H NMR (CHLOROFORM-d ,300MHz): δ = 7.90–8.02 (m, 9H), 7.77–7.89 (m, 6H), 3.54–3.72 (m, 2H), 2.66 (t, J = 6.6 Hz, 2H), 2.04–2.07 p.p.m. (m, 2H). ¹³C NMR (CHLOROFORM-d ,75MHz): δ = 174.0, 136.4, 134.9, 131.6, 120.3, 119.1, 34.2, 34.0, 22.0, 19.2 p.p.m. HRMS (ESI–TOF) m/z: [M⁺] Calcd for C₂₂H₂₂O₂P⁺ 349.381; found 349.1355. [M^-] Calcd for PF₆ 144.965; found 144.9632.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95 to 0.99 Å, O—H = 0.84 Å) and were included in the refinement in the riding model approximation with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Comment top

Organic phosphonium cations have been used as phase transfer catalysts (Starks, 1971), biocidal agents (Kanazawa et al. 1993), and as reagents for Wittig reactions (Hoffman, 2001). There are few examples in the crystallographic literature, however, of triphenylphosphonium cations bearing a carboxylic acid functional group.

In the title compound, 3-carboxypropyltriphenylphosphonium hexafluorophosphate (Fig. 1), crystallizes in a triclinic unit cell with a single cation-anion pair in the asymmetric unit. The dominant intermolecular interactions is hydrogen bonding from the carboxylic acid moiety on the cation (Table 1). The alkyl chain attached to the phosphorous deviates from the expected staggered conformation, showing a rotation at the C1—C2 carbons. This twist in the carbons is likely the cause of the unusual torsion angles observed in the three phenyl rings (Table 2). The phenyl ring that is located under the C2 hydrogens is nearly perpendicular when compared to the other two rings. It is suspected that this perpendicular arrangement of the phenyl ring is assumed to minimize potential steric interactions with the bent portion of the alkyl chain. Interestingly, there are no observed π–π interactions from any of the phenyl rings and there are no weak C—H···F interactions.

Related literature top

For structures of related compounds, see: Li & Mak (1996); Wu et al. (2007). For compounds containing related metallated structures, see: Li & Mak (1997); Sabounchei et al. (2011). For the use of phosphonium compounds as Wittig reagents, see: Hoffman (2001), as biocodal agents, see: Kanazawa et al. (1993) and as phase transfer agents, see: Starks (1971).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. Crystal structure and labeling scheme of compound (1). 50% probablility ellipsoids. Phosphorous is in green, oxygen in red, fluorine in purple, and carbon in grey.

(3-Carboxypropyl)triphenylphosphonium hexafluoridophosphate top

Crystal data top

C₂₂H₂₂O₂P⁺·PF₆⁻	Z = 2
M_r = 494.33	F(000) = 508
Triclinic, P1	D_x = 1.482 Mg m⁻³
a = 9.3307 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6773 (2) Å	Cell parameters from 9960 reflections
c = 12.8129 (2) Å	θ = 2.4–27.8°
α = 72.460 (1)°	µ = 0.26 mm⁻¹
β = 82.307 (1)°	T = 100 K
γ = 65.495 (1)°	Block, colourless
V = 1107.46 (3) Å³	0.29 × 0.16 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	5269 independent reflections
Radiation source: fine-focus sealed tube	4426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 7.9 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω and ϕ scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −14→14
T_min = 0.865, T_max = 0.947	l = −16→16
37843 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0364P)² + 0.4848P] where P = (F_o² + 2F_c²)/3
5269 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₂H₂₂O₂P⁺·PF₆⁻	γ = 65.495 (1)°
M_r = 494.33	V = 1107.46 (3) Å³
Triclinic, P1	Z = 2
a = 9.3307 (1) Å	Mo Kα radiation
b = 10.6773 (2) Å	µ = 0.26 mm⁻¹
c = 12.8129 (2) Å	T = 100 K
α = 72.460 (1)°	0.29 × 0.16 × 0.07 mm
β = 82.307 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5269 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	4426 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.947	R_int = 0.035
37843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
5269 reflections	Δρ_min = −0.36 e Å⁻³
290 parameters

Special details top

Experimental. Absorption correction: SADABS-2014/2 (Bruker, 2014) was used for absorption correction. wR2(int) was 0.0583 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.9133. The λ/2 correction factor is 0.00150.

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.

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

	x	y	z	U_iso*/U_eq
P1	0.42475 (4)	0.61911 (4)	0.72374 (3)	0.01582 (9)
P2	0.21110 (5)	0.22893 (4)	0.72342 (3)	0.02490 (10)
F2	0.18704 (11)	0.33829 (11)	0.79338 (8)	0.0344 (2)
F6	0.13566 (12)	0.36150 (10)	0.61884 (8)	0.0352 (2)
F4	0.23378 (12)	0.12048 (10)	0.65303 (8)	0.0342 (2)
F5	0.03862 (12)	0.23173 (12)	0.76017 (8)	0.0387 (3)
F3	0.38172 (12)	0.22834 (11)	0.68553 (9)	0.0406 (3)
O2	0.48983 (12)	0.17127 (10)	0.96794 (8)	0.0235 (2)
F1	0.28391 (14)	0.09741 (11)	0.82789 (9)	0.0453 (3)
O1	0.66794 (13)	−0.01961 (11)	0.91753 (10)	0.0295 (3)
H1	0.6104	−0.0598	0.9557	0.044*
C5	0.58121 (16)	0.67621 (14)	0.71818 (11)	0.0172 (3)
C18	0.23325 (17)	0.57402 (16)	0.90634 (11)	0.0208 (3)
H18	0.2785	0.4755	0.9084	0.025*
C11	0.32167 (16)	0.70037 (15)	0.59658 (11)	0.0184 (3)
C17	0.28593 (16)	0.67064 (15)	0.82977 (11)	0.0182 (3)
C4	0.60945 (17)	0.11522 (15)	0.91839 (11)	0.0200 (3)
C1	0.51033 (16)	0.42771 (14)	0.74813 (12)	0.0188 (3)
H1A	0.4262	0.3910	0.7713	0.023*
H1B	0.5569	0.4039	0.6789	0.023*
C12	0.25839 (16)	0.62504 (16)	0.55808 (12)	0.0217 (3)
H12	0.2804	0.5273	0.5944	0.026*
C2	0.63811 (16)	0.35274 (15)	0.83609 (12)	0.0207 (3)
H2A	0.7222	0.3896	0.8137	0.025*
H2B	0.5918	0.3743	0.9060	0.025*
C6	0.62009 (17)	0.69945 (15)	0.80985 (12)	0.0213 (3)
H6	0.5526	0.7019	0.8723	0.026*
C19	0.11368 (17)	0.62379 (17)	0.97956 (12)	0.0243 (3)
H19	0.0781	0.5585	1.0325	0.029*
C22	0.22021 (17)	0.81526 (15)	0.82747 (12)	0.0239 (3)
H22	0.2574	0.8806	0.7762	0.029*
C13	0.16332 (17)	0.69379 (18)	0.46650 (12)	0.0255 (3)
H13	0.1208	0.6429	0.4394	0.031*
C3	0.70880 (17)	0.19153 (15)	0.85265 (13)	0.0240 (3)
H3A	0.7292	0.1726	0.7799	0.029*
H3B	0.8116	0.1506	0.8893	0.029*
C14	0.13030 (18)	0.83680 (18)	0.41448 (12)	0.0276 (3)
H14	0.0626	0.8843	0.3530	0.033*
C16	0.29145 (19)	0.84353 (16)	0.54243 (13)	0.0262 (3)
H16	0.3363	0.8942	0.5677	0.031*
C7	0.75827 (17)	0.71902 (16)	0.80929 (13)	0.0253 (3)
H7	0.7852	0.7355	0.8714	0.030*
C8	0.85698 (18)	0.71457 (17)	0.71847 (14)	0.0275 (3)
H8	0.9528	0.7254	0.7193	0.033*
C10	0.67893 (18)	0.67535 (17)	0.62542 (12)	0.0251 (3)
H10	0.6511	0.6618	0.5622	0.030*
C21	0.10050 (19)	0.86258 (17)	0.90047 (13)	0.0296 (3)
H21	0.0552	0.9609	0.8990	0.035*
C20	0.04614 (17)	0.76728 (18)	0.97598 (12)	0.0271 (3)
H20	−0.0373	0.8007	1.0251	0.033*
C9	0.81677 (19)	0.69444 (19)	0.62641 (14)	0.0316 (4)
H9	0.8839	0.6937	0.5637	0.038*
C15	0.1951 (2)	0.91087 (18)	0.45130 (13)	0.0315 (4)
H15	0.1735	1.0083	0.4141	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01569 (17)	0.01745 (17)	0.01619 (17)	−0.00773 (13)	0.00018 (13)	−0.00564 (13)
P2	0.0302 (2)	0.0301 (2)	0.0236 (2)	−0.01993 (18)	−0.00010 (16)	−0.00870 (16)
F2	0.0362 (5)	0.0439 (6)	0.0369 (5)	−0.0220 (5)	0.0021 (4)	−0.0225 (5)
F6	0.0485 (6)	0.0327 (5)	0.0294 (5)	−0.0224 (5)	−0.0021 (4)	−0.0055 (4)
F4	0.0490 (6)	0.0336 (5)	0.0328 (5)	−0.0257 (5)	−0.0006 (4)	−0.0132 (4)
F5	0.0403 (6)	0.0640 (7)	0.0306 (5)	−0.0381 (5)	0.0065 (4)	−0.0166 (5)
F3	0.0308 (5)	0.0479 (6)	0.0599 (7)	−0.0238 (5)	0.0105 (5)	−0.0308 (5)
O2	0.0238 (5)	0.0203 (5)	0.0248 (5)	−0.0076 (4)	0.0042 (4)	−0.0074 (4)
F1	0.0651 (7)	0.0398 (6)	0.0371 (6)	−0.0275 (5)	−0.0218 (5)	−0.0001 (5)
O1	0.0294 (6)	0.0194 (5)	0.0389 (7)	−0.0107 (5)	0.0116 (5)	−0.0102 (5)
C5	0.0165 (6)	0.0172 (6)	0.0193 (7)	−0.0080 (5)	0.0001 (5)	−0.0053 (5)
C18	0.0214 (7)	0.0237 (7)	0.0199 (7)	−0.0115 (6)	−0.0009 (5)	−0.0058 (6)
C11	0.0157 (6)	0.0226 (7)	0.0173 (6)	−0.0076 (5)	0.0014 (5)	−0.0070 (5)
C17	0.0149 (6)	0.0221 (7)	0.0175 (6)	−0.0070 (5)	−0.0012 (5)	−0.0054 (5)
C4	0.0216 (7)	0.0181 (6)	0.0192 (7)	−0.0060 (5)	−0.0033 (5)	−0.0052 (5)
C1	0.0192 (7)	0.0192 (6)	0.0209 (7)	−0.0089 (5)	0.0005 (5)	−0.0077 (5)
C12	0.0193 (7)	0.0283 (7)	0.0208 (7)	−0.0119 (6)	0.0023 (5)	−0.0087 (6)
C2	0.0182 (7)	0.0185 (7)	0.0260 (7)	−0.0077 (5)	−0.0021 (5)	−0.0054 (6)
C6	0.0210 (7)	0.0230 (7)	0.0219 (7)	−0.0089 (6)	0.0002 (6)	−0.0087 (6)
C19	0.0216 (7)	0.0361 (8)	0.0194 (7)	−0.0169 (6)	0.0012 (6)	−0.0060 (6)
C22	0.0244 (7)	0.0200 (7)	0.0238 (7)	−0.0068 (6)	0.0029 (6)	−0.0053 (6)
C13	0.0201 (7)	0.0415 (9)	0.0212 (7)	−0.0151 (7)	0.0017 (6)	−0.0138 (6)
C3	0.0186 (7)	0.0208 (7)	0.0296 (8)	−0.0061 (6)	0.0011 (6)	−0.0055 (6)
C14	0.0199 (7)	0.0402 (9)	0.0183 (7)	−0.0071 (6)	−0.0011 (6)	−0.0084 (6)
C16	0.0319 (8)	0.0241 (7)	0.0248 (8)	−0.0124 (6)	−0.0042 (6)	−0.0060 (6)
C7	0.0233 (7)	0.0252 (7)	0.0307 (8)	−0.0088 (6)	−0.0061 (6)	−0.0108 (6)
C8	0.0209 (7)	0.0291 (8)	0.0361 (9)	−0.0142 (6)	−0.0014 (6)	−0.0070 (7)
C10	0.0264 (8)	0.0345 (8)	0.0204 (7)	−0.0167 (7)	0.0038 (6)	−0.0107 (6)
C21	0.0264 (8)	0.0255 (8)	0.0293 (8)	−0.0020 (6)	0.0028 (6)	−0.0102 (6)
C20	0.0175 (7)	0.0396 (9)	0.0217 (7)	−0.0071 (6)	0.0029 (6)	−0.0122 (7)
C9	0.0264 (8)	0.0440 (10)	0.0297 (8)	−0.0213 (7)	0.0081 (7)	−0.0108 (7)
C15	0.0356 (9)	0.0268 (8)	0.0251 (8)	−0.0078 (7)	−0.0054 (7)	−0.0018 (6)

Geometric parameters (Å, º) top

P1—C5	1.7867 (14)	C2—H2B	0.9900
P1—C11	1.7910 (14)	C2—C3	1.5227 (19)
P1—C17	1.7930 (14)	C6—H6	0.9500
P1—C1	1.8000 (14)	C6—C7	1.388 (2)
P2—F2	1.6053 (10)	C19—H19	0.9500
P2—F6	1.6054 (10)	C19—C20	1.382 (2)
P2—F4	1.6044 (10)	C22—H22	0.9500
P2—F5	1.6058 (10)	C22—C21	1.384 (2)
P2—F3	1.5990 (10)	C13—H13	0.9500
P2—F1	1.5951 (11)	C13—C14	1.386 (2)
O2—C4	1.2216 (17)	C3—H3A	0.9900
O1—H1	0.8400	C3—H3B	0.9900
O1—C4	1.3140 (17)	C14—H14	0.9500
C5—C6	1.3919 (19)	C14—C15	1.382 (2)
C5—C10	1.3977 (19)	C16—H16	0.9500
C18—H18	0.9500	C16—C15	1.388 (2)
C18—C17	1.3964 (19)	C7—H7	0.9500
C18—C19	1.391 (2)	C7—C8	1.384 (2)
C11—C12	1.396 (2)	C8—H8	0.9500
C11—C16	1.397 (2)	C8—C9	1.384 (2)
C17—C22	1.3975 (19)	C10—H10	0.9500
C4—C3	1.496 (2)	C10—C9	1.385 (2)
C1—H1A	0.9900	C21—H21	0.9500
C1—H1B	0.9900	C21—C20	1.390 (2)
C1—C2	1.5352 (19)	C20—H20	0.9500
C12—H12	0.9500	C9—H9	0.9500
C12—C13	1.386 (2)	C15—H15	0.9500
C2—H2A	0.9900

C5—P1—C11	110.19 (6)	C3—C2—C1	110.82 (12)
C5—P1—C17	110.68 (6)	C3—C2—H2A	109.5
C5—P1—C1	107.80 (6)	C3—C2—H2B	109.5
C11—P1—C17	107.83 (6)	C5—C6—H6	120.3
C11—P1—C1	109.51 (6)	C7—C6—C5	119.50 (13)
C17—P1—C1	110.83 (7)	C7—C6—H6	120.3
F2—P2—F6	89.92 (5)	C18—C19—H19	119.7
F2—P2—F5	89.94 (5)	C20—C19—C18	120.63 (14)
F6—P2—F5	89.47 (6)	C20—C19—H19	119.7
F4—P2—F2	179.53 (6)	C17—C22—H22	120.3
F4—P2—F6	89.72 (5)	C21—C22—C17	119.49 (14)
F4—P2—F5	89.76 (5)	C21—C22—H22	120.3
F3—P2—F2	89.89 (5)	C12—C13—H13	120.0
F3—P2—F6	89.71 (6)	C12—C13—C14	119.99 (14)
F3—P2—F4	90.41 (5)	C14—C13—H13	120.0
F3—P2—F5	179.17 (7)	C4—C3—C2	115.15 (12)
F1—P2—F2	89.99 (6)	C4—C3—H3A	108.5
F1—P2—F6	179.28 (6)	C4—C3—H3B	108.5
F1—P2—F4	90.37 (6)	C2—C3—H3A	108.5
F1—P2—F5	89.82 (6)	C2—C3—H3B	108.5
F1—P2—F3	91.00 (6)	H3A—C3—H3B	107.5
C4—O1—H1	109.5	C13—C14—H14	119.7
C6—C5—P1	120.87 (11)	C15—C14—C13	120.53 (14)
C6—C5—C10	120.30 (13)	C15—C14—H14	119.7
C10—C5—P1	118.10 (11)	C11—C16—H16	120.4
C17—C18—H18	120.4	C15—C16—C11	119.24 (15)
C19—C18—H18	120.4	C15—C16—H16	120.4
C19—C18—C17	119.17 (13)	C6—C7—H7	119.9
C12—C11—P1	119.73 (11)	C8—C7—C6	120.18 (14)
C12—C11—C16	120.37 (13)	C8—C7—H7	119.9
C16—C11—P1	119.58 (11)	C7—C8—H8	119.8
C18—C17—P1	121.95 (11)	C7—C8—C9	120.35 (14)
C18—C17—C22	120.34 (13)	C9—C8—H8	119.8
C22—C17—P1	117.45 (11)	C5—C10—H10	120.3
O2—C4—O1	124.32 (13)	C9—C10—C5	119.44 (14)
O2—C4—C3	123.95 (13)	C9—C10—H10	120.3
O1—C4—C3	111.72 (12)	C22—C21—H21	119.8
P1—C1—H1A	109.1	C22—C21—C20	120.45 (14)
P1—C1—H1B	109.1	C20—C21—H21	119.8
H1A—C1—H1B	107.8	C19—C20—C21	119.90 (14)
C2—C1—P1	112.67 (9)	C19—C20—H20	120.1
C2—C1—H1A	109.1	C21—C20—H20	120.1
C2—C1—H1B	109.1	C8—C9—C10	120.20 (14)
C11—C12—H12	120.2	C8—C9—H9	119.9
C13—C12—C11	119.56 (14)	C10—C9—H9	119.9
C13—C12—H12	120.2	C14—C15—C16	120.28 (15)
C1—C2—H2A	109.5	C14—C15—H15	119.9
C1—C2—H2B	109.5	C16—C15—H15	119.9
H2A—C2—H2B	108.1

P1—C5—C6—C7	168.72 (11)	C17—P1—C11—C12	−92.86 (12)
P1—C5—C10—C9	−168.71 (12)	C17—P1—C11—C16	80.66 (13)
P1—C11—C12—C13	172.55 (11)	C17—P1—C1—C2	−77.68 (11)
P1—C11—C16—C15	−172.12 (12)	C17—C18—C19—C20	0.8 (2)
P1—C17—C22—C21	173.20 (12)	C17—C22—C21—C20	0.3 (2)
P1—C1—C2—C3	−179.11 (10)	C1—P1—C5—C6	−96.79 (12)
O2—C4—C3—C2	−9.1 (2)	C1—P1—C5—C6	−96.79 (12)
O1—C4—C3—C2	171.88 (13)	C1—P1—C5—C10	73.39 (13)
C5—P1—C11—C12	146.24 (11)	C1—P1—C11—C12	27.83 (13)
C5—P1—C11—C16	−40.23 (13)	C1—P1—C11—C12	27.83 (13)
C5—P1—C17—C18	−131.04 (12)	C1—P1—C11—C16	−158.65 (11)
C5—P1—C17—C22	54.76 (13)	C1—P1—C17—C18	−11.48 (14)
C5—P1—C1—C2	43.58 (12)	C1—P1—C17—C18	−11.48 (14)
C5—C6—C7—C8	−0.4 (2)	C1—P1—C17—C22	174.32 (11)
C5—C10—C9—C8	−0.2 (2)	C1—C2—C3—C4	−77.18 (16)
C18—C17—C22—C21	−1.1 (2)	C12—C11—C16—C15	1.4 (2)
C18—C19—C20—C21	−1.6 (2)	C12—C13—C14—C15	1.8 (2)
C11—P1—C5—C6	143.74 (11)	C6—C5—C10—C9	1.5 (2)
C11—P1—C5—C10	−46.07 (13)	C6—C7—C8—C9	1.7 (2)
C11—P1—C17—C18	108.38 (12)	C19—C18—C17—P1	−173.47 (11)
C11—P1—C17—C22	−65.82 (13)	C19—C18—C17—C22	0.6 (2)
C11—P1—C1—C2	163.47 (10)	C22—C21—C20—C19	1.1 (2)
C11—C12—C13—C14	−0.7 (2)	C13—C14—C15—C16	−1.4 (2)
C11—C16—C15—C14	−0.2 (2)	C16—C11—C12—C13	−0.9 (2)
C17—P1—C5—C6	24.57 (14)	C7—C8—C9—C10	−1.5 (3)
C17—P1—C5—C10	−165.24 (11)	C10—C5—C6—C7	−1.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.80	2.6285 (15)	171
C1—H1A···F2	0.99	2.48	3.455 (2)	168
C1—H1A···F3	0.99	2.50	3.1656 (19)	124
C22—H22···F4ⁱⁱ	0.95	2.51	3.3924 (18)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.80	2.6285 (15)	171
C1—H1A···F2	0.99	2.48	3.455 (2)	168
C1—H1A···F3	0.99	2.50	3.1656 (19)	124
C22—H22···F4ⁱⁱ	0.95	2.51	3.3924 (18)	155

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

Acknowledgements

The authors wish to acknowledge the Mississippi State University Department of Chemistry for funding.

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Volume 70| Part 11| November 2014| Pages o1197-o1198

doi:10.1107/S160053681402323X

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

Crystal structure of (3-carb­­oxy­prop­yl)tri­phenyl­phospho­nium hexa­fluorido­phosphate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (3-carboxypropyl)triphenylphosphonium hexafluoridophosphate