Tetra­phenyl­phospho­nium chloride dihydrate

Blake, A.J.; Garner, C.D.; Tunney, J.M.

doi:10.1107/S1600536802021682

Tetraphenylphosphonium chloride dihydrate

A. J. Blake, C. D. Garner and J. M. Tunney

The structure of the title compound, C₂₄H₂₀P⁺·Cl^-·2H₂O, comprises hydrogen-bonded chains of water molecules and chloride anions separated by hydrophobic regions of tetraphenylphosphonium cations. Within the hydrogen-bonded chains the chloride anions are bridged by pairs of water molecules. Each water molecule donates two hydrogen bonds, while each chloride accepts four.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021682/na6187sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021682/na6187Isup2.hkl Contains datablock I

CCDC reference: 202982

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.097
Data-to-parameter ratio = 20.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.56
         From the CIF: _reflns_number_total               5302
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5952
         Completeness (_total/calc)             89.08%
          Alert B: < 90% complete (theta max?)

Author response: ... Data are >98% complete to 2theta = 55 degrees.


 Alert Level C:



PLAT_731  Alert C Bond    Calc     0.85(2), Rep    0.844(9) ....       2.22 su-Ratio
                     O2W  -H2W2    1.555   1.555


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PLATON.

(I) top

Crystal data top

C₂₄H₂₀P⁺·Cl⁻·2H₂O	Z = 2
M_r = 410.85	F(000) = 432
Triclinic, P1	D_x = 1.285 Mg m⁻³
a = 9.4849 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0024 (13) Å	Cell parameters from 4088 reflections
c = 11.4028 (13) Å	θ = 2.3–29.6°
α = 75.090 (2)°	µ = 0.27 mm⁻¹
β = 73.748 (2)°	T = 150 K
γ = 71.050 (2)°	Tablet, pale orange
V = 1062.2 (4) Å³	0.44 × 0.28 × 0.14 mm

Data collection top

Bruker SMART1000 CCD area-detector diffractometer	5302 independent reflections
Radiation source: normal-focus sealed tube	4045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 29.6°, θ_min = 2.3°
Absorption correction: multi-scan (SHEXLTL; Bruker, 2001)	h = −12→13
T_min = 0.876, T_max = 0.961	k = −15→15
9902 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: see text
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.051P)²P] where P = (F_o² + 2F_c²)/3
5295 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.41 e Å⁻³
6 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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
P	0.50410 (4)	0.69699 (3)	0.15847 (3)	0.01997 (10)
C1	0.34033 (16)	0.75197 (14)	0.09061 (14)	0.0265 (3)
C2	0.19359 (18)	0.77650 (16)	0.16605 (17)	0.0374 (4)
H2	0.1800	0.7611	0.2539	0.045*
C3	0.0684 (2)	0.82339 (18)	0.1114 (2)	0.0569 (6)
H3	−0.0316	0.8419	0.1619	0.068*
C4	0.0883 (2)	0.84343 (18)	−0.0165 (2)	0.0605 (7)
H4	0.0017	0.8759	−0.0532	0.073*
C5	0.2316 (2)	0.81683 (17)	−0.09041 (19)	0.0506 (5)
H5	0.2438	0.8297	−0.1779	0.061*
C6	0.3588 (2)	0.77136 (15)	−0.03842 (15)	0.0344 (4)
H6	0.4582	0.7534	−0.0900	0.041*
C7	0.50322 (16)	0.54754 (13)	0.26778 (12)	0.0217 (3)
C8	0.38892 (17)	0.48556 (14)	0.29076 (14)	0.0282 (3)
H8	0.3069	0.5228	0.2488	0.034*
C9	0.39562 (19)	0.36908 (15)	0.37541 (15)	0.0333 (4)
H9	0.3174	0.3268	0.3924	0.040*
C10	0.51631 (19)	0.31449 (14)	0.43514 (13)	0.0305 (3)
H10	0.5205	0.2344	0.4927	0.037*
C11	0.63111 (18)	0.37503 (14)	0.41211 (14)	0.0302 (3)
H11	0.7139	0.3362	0.4531	0.036*
C12	0.62464 (17)	0.49223 (14)	0.32927 (13)	0.0261 (3)
H12	0.7021	0.5350	0.3141	0.031*
C13	0.67140 (15)	0.66989 (13)	0.03733 (12)	0.0221 (3)
C14	0.74626 (17)	0.54517 (14)	0.01137 (14)	0.0283 (3)
H14	0.7138	0.4719	0.0623	0.034*
C15	0.86883 (19)	0.52847 (16)	−0.08955 (15)	0.0364 (4)
H15	0.9201	0.4435	−0.1080	0.044*
C16	0.91616 (18)	0.63484 (16)	−0.16297 (14)	0.0359 (4)
H16	1.0005	0.6227	−0.2314	0.043*
C17	0.84178 (18)	0.75922 (16)	−0.13776 (14)	0.0330 (4)
H17	0.8745	0.8321	−0.1893	0.040*
C18	0.71999 (17)	0.77734 (14)	−0.03769 (13)	0.0278 (3)
H18	0.6693	0.8626	−0.0199	0.033*
C19	0.51120 (16)	0.82112 (13)	0.23179 (12)	0.0230 (3)
C20	0.38172 (19)	0.91929 (14)	0.26919 (14)	0.0321 (3)
H20	0.2859	0.9232	0.2555	0.038*
C21	0.3936 (2)	1.01175 (16)	0.32684 (15)	0.0414 (4)
H21	0.3057	1.0789	0.3527	0.050*
C22	0.5313 (2)	1.00606 (16)	0.34626 (14)	0.0420 (4)
H22	0.5388	1.0706	0.3840	0.050*
C23	0.6600 (2)	0.90769 (17)	0.31177 (15)	0.0383 (4)
H23	0.7547	0.9037	0.3275	0.046*
C24	0.65080 (18)	0.81451 (15)	0.25397 (14)	0.0295 (3)
H24	0.7390	0.7469	0.2298	0.035*
Cl	1.01260 (5)	0.24133 (4)	0.50226 (4)	0.03494 (11)
O1W	0.93724 (16)	0.56252 (12)	0.35572 (11)	0.0429 (3)
H1W1	0.953 (2)	0.4873 (11)	0.4013 (17)	0.064*
H1W2	0.951 (2)	0.6097 (16)	0.3970 (17)	0.064*
O2W	0.94310 (19)	0.05637 (13)	0.34577 (11)	0.0538 (4)
H2W1	0.956 (3)	−0.0200 (11)	0.3892 (19)	0.081*
H2W2	0.947 (3)	0.1019 (18)	0.3937 (18)	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.02080 (18)	0.01892 (18)	0.02039 (18)	−0.00612 (14)	−0.00476 (14)	−0.00265 (13)
C1	0.0255 (7)	0.0220 (7)	0.0339 (8)	−0.0097 (6)	−0.0116 (6)	0.0013 (6)
C2	0.0266 (8)	0.0299 (8)	0.0528 (11)	−0.0095 (7)	−0.0087 (7)	−0.0002 (7)
C3	0.0272 (9)	0.0367 (10)	0.1045 (19)	−0.0116 (8)	−0.0231 (11)	0.0045 (11)
C4	0.0548 (13)	0.0387 (11)	0.1009 (18)	−0.0227 (10)	−0.0555 (13)	0.0205 (11)
C5	0.0702 (14)	0.0391 (10)	0.0601 (12)	−0.0308 (10)	−0.0473 (11)	0.0177 (9)
C6	0.0434 (9)	0.0313 (8)	0.0359 (9)	−0.0185 (7)	−0.0200 (7)	0.0048 (7)
C7	0.0254 (7)	0.0192 (7)	0.0199 (7)	−0.0072 (5)	−0.0036 (5)	−0.0026 (5)
C8	0.0303 (8)	0.0267 (8)	0.0308 (8)	−0.0110 (6)	−0.0097 (6)	−0.0029 (6)
C9	0.0413 (9)	0.0282 (8)	0.0331 (9)	−0.0177 (7)	−0.0051 (7)	−0.0030 (6)
C10	0.0476 (10)	0.0198 (7)	0.0221 (7)	−0.0102 (7)	−0.0053 (7)	−0.0019 (6)
C11	0.0374 (9)	0.0262 (8)	0.0249 (8)	−0.0024 (7)	−0.0108 (6)	−0.0047 (6)
C12	0.0268 (7)	0.0257 (7)	0.0261 (8)	−0.0069 (6)	−0.0063 (6)	−0.0045 (6)
C13	0.0230 (7)	0.0246 (7)	0.0192 (7)	−0.0063 (6)	−0.0048 (5)	−0.0050 (5)
C14	0.0336 (8)	0.0258 (8)	0.0260 (8)	−0.0078 (6)	−0.0065 (6)	−0.0060 (6)
C15	0.0376 (9)	0.0330 (9)	0.0333 (9)	0.0008 (7)	−0.0042 (7)	−0.0142 (7)
C16	0.0323 (9)	0.0444 (10)	0.0251 (8)	−0.0064 (7)	0.0014 (7)	−0.0097 (7)
C17	0.0326 (8)	0.0370 (9)	0.0254 (8)	−0.0113 (7)	−0.0019 (6)	−0.0013 (7)
C18	0.0297 (8)	0.0250 (7)	0.0265 (8)	−0.0081 (6)	−0.0020 (6)	−0.0044 (6)
C19	0.0304 (8)	0.0200 (7)	0.0188 (7)	−0.0092 (6)	−0.0045 (6)	−0.0017 (5)
C20	0.0385 (9)	0.0258 (8)	0.0273 (8)	−0.0016 (7)	−0.0086 (7)	−0.0043 (6)
C21	0.0638 (12)	0.0240 (8)	0.0298 (9)	−0.0002 (8)	−0.0107 (8)	−0.0078 (7)
C22	0.0831 (14)	0.0251 (8)	0.0239 (8)	−0.0217 (9)	−0.0133 (8)	−0.0036 (6)
C23	0.0545 (11)	0.0416 (10)	0.0307 (9)	−0.0294 (8)	−0.0095 (8)	−0.0053 (7)
C24	0.0318 (8)	0.0304 (8)	0.0297 (8)	−0.0142 (7)	−0.0049 (6)	−0.0059 (6)
Cl	0.0448 (2)	0.0287 (2)	0.0362 (2)	−0.01198 (17)	−0.01565 (18)	−0.00429 (16)
O1W	0.0602 (8)	0.0362 (7)	0.0392 (7)	−0.0113 (6)	−0.0218 (6)	−0.0085 (5)
O2W	0.0965 (11)	0.0409 (7)	0.0381 (7)	−0.0340 (8)	−0.0298 (8)	0.0052 (6)

Geometric parameters (Å, º) top

P—C1	1.7886 (14)	C13—C14	1.391 (2)
P—C7	1.7905 (14)	C13—C18	1.3981 (19)
P—C13	1.7868 (14)	C14—C15	1.389 (2)
P—C19	1.8021 (14)	C14—H14	0.9500
C1—C2	1.398 (2)	C15—C16	1.378 (2)
C1—C6	1.400 (2)	C15—H15	0.9500
C2—C3	1.384 (2)	C16—C17	1.384 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.385 (3)	C17—C18	1.381 (2)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.368 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C24	1.392 (2)
C5—C6	1.384 (2)	C19—C20	1.393 (2)
C5—H5	0.9500	C20—C21	1.393 (2)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.392 (2)	C21—C22	1.364 (3)
C7—C12	1.4020 (19)	C21—H21	0.9500
C8—C9	1.387 (2)	C22—C23	1.381 (3)
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.384 (2)	C23—C24	1.390 (2)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.385 (2)	C24—H24	0.9500
C10—H10	0.9500	O1W—H1W1	0.848 (9)
C11—C12	1.3832 (19)	O1W—H1W2	0.846 (9)
C11—H11	0.9500	O2W—H2W1	0.848 (9)
C12—H12	0.9500	O2W—H2W2	0.844 (9)

C13—P—C1	108.49 (7)	C11—C12—H12	120.2
C13—P—C7	109.08 (6)	C7—C12—H12	120.2
C1—P—C7	110.80 (7)	C14—C13—C18	119.95 (13)
C13—P—C19	107.39 (6)	C14—C13—P	120.83 (11)
C1—P—C19	110.35 (7)	C18—C13—P	119.04 (10)
C7—P—C19	110.65 (6)	C15—C14—C13	119.56 (14)
C2—C1—C6	119.81 (14)	C15—C14—H14	120.2
C2—C1—P	120.19 (12)	C13—C14—H14	120.2
C6—C1—P	120.00 (12)	C16—C15—C14	120.15 (14)
C3—C2—C1	119.28 (17)	C16—C15—H15	119.9
C3—C2—H2	120.4	C14—C15—H15	119.9
C1—C2—H2	120.4	C15—C16—C17	120.53 (14)
C2—C3—C4	120.33 (19)	C15—C16—H16	119.7
C2—C3—H3	119.8	C17—C16—H16	119.7
C4—C3—H3	119.8	C18—C17—C16	119.99 (15)
C5—C4—C3	120.55 (17)	C18—C17—H17	120.0
C5—C4—H4	119.7	C16—C17—H17	120.0
C3—C4—H4	119.7	C17—C18—C13	119.82 (13)
C4—C5—C6	120.36 (18)	C17—C18—H18	120.1
C4—C5—H5	119.8	C13—C18—H18	120.1
C6—C5—H5	119.8	C24—C19—C20	120.02 (14)
C5—C6—C1	119.65 (17)	C24—C19—P	117.92 (11)
C5—C6—H6	120.2	C20—C19—P	122.03 (12)
C1—C6—H6	120.2	C19—C20—C21	119.54 (16)
C8—C7—C12	120.24 (13)	C19—C20—H20	120.2
C8—C7—P	122.23 (11)	C21—C20—H20	120.2
C12—C7—P	117.52 (11)	C22—C21—C20	120.11 (16)
C9—C8—C7	119.51 (14)	C22—C21—H21	119.9
C9—C8—H8	120.2	C20—C21—H21	119.9
C7—C8—H8	120.2	C21—C22—C23	120.89 (15)
C10—C9—C8	119.98 (14)	C21—C22—H22	119.6
C10—C9—H9	120.0	C23—C22—H22	119.6
C8—C9—H9	120.0	C22—C23—C24	119.95 (16)
C9—C10—C11	120.87 (14)	C22—C23—H23	120.0
C9—C10—H10	119.6	C24—C23—H23	120.0
C11—C10—H10	119.6	C23—C24—C19	119.46 (15)
C12—C11—C10	119.74 (14)	C23—C24—H24	120.3
C12—C11—H11	120.1	C19—C24—H24	120.3
C10—C11—H11	120.1	H1W1—O1W—H1W2	104 (2)
C11—C12—C7	119.65 (14)	H2W1—O2W—H2W2	103 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···Cl	0.85 (1)	2.60 (1)	3.4322 (13)	169 (2)
O1W—H1W2···Clⁱ	0.85 (2)	2.38 (2)	3.2253 (12)	175 (2)
O2W—H2W1···Clⁱⁱ	0.85 (1)	2.39 (2)	3.2405 (13)	175 (2)
O2W—H2W2···Cl	0.84 (3)	2.51 (3)	3.3405 (13)	167 (2)

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

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Tetra­phenyl­phospho­nium chloride dihydrate

Supporting information

Key indicators

checkCIF results

Tetraphenylphosphonium chloride dihydrate