Crystal structure of benzyl-tri-phenyl-phospho-nium chloride monohydrate.

The title compound, Ph3(PhCH2)P(+)·Cl(-)·H2O, was obtained unintentionally as the product of an attempted synthesis of a silver di-thio-carbamate complex using benzyl-tri-phenyl-phospho-nium as the counter-ion. The asymmetric unit consists of a phospho-nium cation and a chloride anion, and a water mol-ecule of crystallization. In the crystal, the chloride ion is linked to the water mol-ecule by an O-H⋯Cl hydrogen bond. The three units are further linked via C-H⋯Cl and C-H⋯O hydrogen bonds and C-H⋯ π inter-actions, forming a three-dimensional structure.

Related literature

For some structures containing the Ph3(PhCH2)P+ cation, see: Li & He (2011 ▸); Fischer & Wiebelhaus (1997 ▸); Skapski & Stephens (1974 ▸).

Experimental

Crystal data

C25H22P+·Cl−·H2O

M = 406.86

Monoclinic,

a = 9.7368 (8) Å

b = 19.7474 (17) Å

c = 11.4170 (9) Å

β = 109.728 (9)°

V = 2066.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent 2013 ▸) T min = 0.813, T max = 1.000

12625 measured reflections

5434 independent reflections

3901 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.194

S = 1.07

5434 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.72 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: OLEX2.solve (Bourhis et al., 2015 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015009159/su5134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009159/su5134Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009159/su5134Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009159/su5134fig1.tif

The asymmetric unit of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Dotted line denotes the O—H⋯Cl hydrogen bond (see Table 1 for details).

CCDC reference: 1400555

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H22P+·Cl−·H2O	F(000) = 856
Mr = 406.86	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7368 (8) Å	Cell parameters from 2649 reflections
b = 19.7474 (17) Å	θ = 3.6–30.1°
c = 11.4170 (9) Å	µ = 0.28 mm−1
β = 109.728 (9)°	T = 100 K
V = 2066.4 (3) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	5434 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3901 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.067
Detector resolution: 10.4041 pixels mm-1	θmax = 30.3°, θmin = 3.0°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent 2013)	k = −26→18
Tmin = 0.813, Tmax = 1.000	l = −16→15
12625 measured reflections

Refinement on F2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0844P)2 + 1.2017P] where P = (Fo2 + 2Fc2)/3
5434 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.90 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

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.Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation with Uiso(H) = 1.2Ueq(C). H atoms in water molecule (O–H 0.85 Å) were refined using a riding model with Uiso(H) = 1.5Ueq(O).

	x	y	z	Uiso*/Ueq
Cl1	0.25025 (7)	0.57674 (4)	0.31223 (6)	0.02397 (19)
P1	0.34083 (7)	0.36232 (3)	0.34126 (5)	0.01553 (18)
C18	0.2330 (3)	0.37275 (14)	−0.0334 (2)	0.0213 (5)
H18	0.2775	0.3645	−0.0923	0.026*
C7	0.4679 (3)	0.43096 (13)	0.3966 (2)	0.0178 (5)
H7A	0.4141	0.4727	0.3933	0.021*
H7B	0.5262	0.4227	0.4829	0.021*
C8	0.4377 (3)	0.28343 (13)	0.3638 (2)	0.0173 (5)
C24	0.0575 (3)	0.29764 (17)	0.5078 (2)	0.0270 (6)
H24	0.0103	0.2574	0.5131	0.032*
C3	0.7862 (3)	0.41102 (16)	0.2782 (3)	0.0260 (6)
H3	0.8712	0.3856	0.2960	0.031*
C13	0.5493 (3)	0.27260 (14)	0.4777 (2)	0.0219 (6)
H13	0.5710	0.3055	0.5396	0.026*
C20	0.2189 (3)	0.36118 (14)	0.4295 (2)	0.0187 (5)
C5	0.6222 (3)	0.49415 (15)	0.1536 (2)	0.0239 (6)
H5	0.5977	0.5252	0.0885	0.029*
C6	0.5303 (3)	0.48535 (14)	0.2233 (2)	0.0205 (5)
H6	0.4441	0.5100	0.2042	0.025*
C4	0.7491 (3)	0.45721 (15)	0.1805 (2)	0.0246 (6)
H4	0.8098	0.4631	0.1334	0.030*
C15	0.0985 (3)	0.39724 (15)	0.1413 (2)	0.0226 (6)
H15	0.0535	0.4058	0.1998	0.027*
C14	0.2409 (3)	0.37351 (13)	0.1790 (2)	0.0163 (5)
C19	0.3092 (3)	0.36202 (13)	0.0909 (2)	0.0195 (5)
H19	0.4054	0.3472	0.1161	0.023*
C1	0.5683 (3)	0.43952 (13)	0.3214 (2)	0.0174 (5)
C10	0.4851 (3)	0.17419 (15)	0.2931 (3)	0.0257 (6)
H10	0.4640	0.1412	0.2313	0.031*
C11	0.5955 (3)	0.16351 (16)	0.4041 (3)	0.0290 (6)
H11	0.6491	0.1236	0.4171	0.035*
C16	0.0233 (3)	0.40826 (16)	0.0154 (2)	0.0263 (6)
H16	−0.0722	0.4241	−0.0103	0.032*
C17	0.0900 (3)	0.39582 (15)	−0.0711 (2)	0.0240 (6)
H17	0.0391	0.4029	−0.1552	0.029*
C9	0.4051 (3)	0.23357 (14)	0.2723 (2)	0.0215 (5)
H9	0.3297	0.2402	0.1973	0.026*
C22	0.1048 (3)	0.41462 (18)	0.5617 (3)	0.0313 (7)
H22	0.0892	0.4528	0.6031	0.038*
C25	0.1486 (3)	0.30063 (15)	0.4365 (2)	0.0223 (6)
H25	0.1624	0.2625	0.3939	0.027*
C12	0.6270 (3)	0.21230 (16)	0.4971 (3)	0.0282 (6)
H12	0.7006	0.2045	0.5727	0.034*
C21	0.1962 (3)	0.41847 (16)	0.4911 (2)	0.0255 (6)
H21	0.2418	0.4591	0.4851	0.031*
C2	0.6968 (3)	0.40286 (15)	0.3491 (2)	0.0224 (6)
H2	0.7229	0.3727	0.4155	0.027*
C23	0.0372 (3)	0.35462 (17)	0.5707 (2)	0.0294 (7)
H23	−0.0224	0.3523	0.6193	0.035*
O1	0.8349 (4)	0.22715 (17)	0.2572 (3)	0.0728 (10)
H1A	0.8551	0.2282	0.3357	0.109*
H1B	0.8042	0.1879	0.2301	0.109*

	U11	U22	U33	U12	U13	U23
Cl1	0.0225 (3)	0.0253 (4)	0.0235 (3)	0.0063 (3)	0.0070 (2)	0.0027 (2)
P1	0.0149 (3)	0.0154 (3)	0.0171 (3)	0.0005 (2)	0.0063 (2)	−0.0006 (2)
C18	0.0283 (14)	0.0186 (13)	0.0210 (11)	−0.0047 (11)	0.0135 (10)	−0.0034 (10)
C7	0.0177 (12)	0.0158 (13)	0.0201 (11)	−0.0006 (10)	0.0066 (9)	−0.0017 (9)
C8	0.0164 (11)	0.0161 (13)	0.0228 (11)	0.0015 (10)	0.0112 (9)	0.0031 (9)
C24	0.0219 (13)	0.0311 (16)	0.0307 (14)	0.0016 (13)	0.0124 (11)	0.0099 (12)
C3	0.0193 (13)	0.0267 (16)	0.0328 (14)	0.0012 (12)	0.0098 (11)	0.0016 (11)
C13	0.0210 (13)	0.0214 (14)	0.0240 (12)	0.0010 (11)	0.0083 (10)	0.0020 (10)
C20	0.0163 (12)	0.0243 (14)	0.0147 (11)	0.0036 (11)	0.0043 (9)	0.0014 (9)
C5	0.0281 (14)	0.0210 (14)	0.0211 (12)	−0.0041 (12)	0.0063 (10)	0.0025 (10)
C6	0.0183 (12)	0.0174 (13)	0.0245 (12)	−0.0019 (11)	0.0054 (9)	−0.0005 (10)
C4	0.0250 (14)	0.0258 (16)	0.0278 (13)	−0.0045 (12)	0.0152 (11)	−0.0001 (11)
C15	0.0200 (13)	0.0278 (15)	0.0206 (11)	0.0038 (12)	0.0079 (10)	−0.0007 (10)
C14	0.0177 (12)	0.0157 (12)	0.0157 (10)	−0.0024 (10)	0.0059 (9)	−0.0013 (9)
C19	0.0194 (12)	0.0171 (13)	0.0242 (12)	−0.0001 (10)	0.0102 (10)	−0.0008 (10)
C1	0.0147 (11)	0.0151 (12)	0.0217 (11)	−0.0028 (10)	0.0053 (9)	−0.0020 (9)
C10	0.0310 (15)	0.0169 (14)	0.0336 (14)	−0.0013 (12)	0.0165 (12)	−0.0020 (11)
C11	0.0287 (15)	0.0198 (15)	0.0414 (15)	0.0066 (13)	0.0157 (12)	0.0032 (12)
C16	0.0208 (13)	0.0320 (17)	0.0242 (13)	0.0045 (12)	0.0053 (10)	0.0010 (11)
C17	0.0291 (14)	0.0220 (14)	0.0187 (11)	−0.0037 (12)	0.0053 (10)	0.0013 (10)
C9	0.0232 (13)	0.0172 (13)	0.0253 (12)	0.0002 (11)	0.0097 (10)	0.0007 (10)
C22	0.0288 (15)	0.042 (2)	0.0265 (13)	0.0001 (14)	0.0136 (12)	−0.0091 (12)
C25	0.0245 (13)	0.0207 (14)	0.0247 (12)	0.0017 (11)	0.0124 (10)	0.0041 (10)
C12	0.0243 (14)	0.0256 (16)	0.0332 (14)	0.0043 (12)	0.0076 (11)	0.0080 (12)
C21	0.0232 (13)	0.0265 (16)	0.0289 (13)	−0.0035 (12)	0.0115 (11)	−0.0078 (11)
C2	0.0191 (12)	0.0230 (14)	0.0243 (12)	−0.0028 (11)	0.0063 (10)	0.0028 (10)
C23	0.0230 (13)	0.047 (2)	0.0214 (12)	0.0061 (14)	0.0116 (11)	0.0058 (12)
O1	0.080 (2)	0.053 (2)	0.0685 (19)	−0.0064 (18)	0.0032 (18)	−0.0002 (15)

P1—C7	1.800 (3)	C4—H4	0.9300
P1—C8	1.794 (3)	C15—H15	0.9300
P1—C20	1.798 (3)	C15—C14	1.387 (4)
P1—C14	1.792 (2)	C15—C16	1.393 (4)
C18—H18	0.9300	C14—C19	1.398 (3)
C18—C19	1.378 (3)	C19—H19	0.9300
C18—C17	1.388 (4)	C1—C2	1.386 (4)
C7—H7A	0.9700	C10—H10	0.9300
C7—H7B	0.9700	C10—C11	1.374 (4)
C7—C1	1.512 (4)	C10—C9	1.383 (4)
C8—C13	1.401 (4)	C11—H11	0.9300
C8—C9	1.392 (4)	C11—C12	1.389 (4)
C24—H24	0.9300	C16—H16	0.9300
C24—C25	1.392 (4)	C16—C17	1.374 (4)
C24—C23	1.385 (4)	C17—H17	0.9300
C3—H3	0.9300	C9—H9	0.9300
C3—C4	1.391 (4)	C22—H22	0.9300
C3—C2	1.384 (4)	C22—C21	1.390 (4)
C13—H13	0.9300	C22—C23	1.376 (5)
C13—C12	1.388 (4)	C25—H25	0.9300
C20—C25	1.394 (4)	C12—H12	0.9300
C20—C21	1.388 (4)	C21—H21	0.9300
C5—H5	0.9300	C2—H2	0.9300
C5—C6	1.395 (4)	C23—H23	0.9300
C5—C4	1.377 (4)	O1—H1A	0.8504
C6—H6	0.9300	O1—H1B	0.8496
C6—C1	1.390 (4)
C8—P1—C7	109.74 (12)	C15—C14—C19	120.0 (2)
C8—P1—C20	108.86 (12)	C19—C14—P1	119.98 (19)
C20—P1—C7	108.56 (12)	C18—C19—C14	119.6 (2)
C14—P1—C7	109.82 (12)	C18—C19—H19	120.2
C14—P1—C8	109.33 (12)	C14—C19—H19	120.2
C14—P1—C20	110.51 (11)	C6—C1—C7	118.9 (2)
C19—C18—H18	119.8	C2—C1—C7	121.2 (2)
C19—C18—C17	120.3 (2)	C2—C1—C6	119.9 (2)
C17—C18—H18	119.8	C11—C10—H10	119.7
P1—C7—H7A	109.1	C11—C10—C9	120.5 (3)
P1—C7—H7B	109.1	C9—C10—H10	119.7
H7A—C7—H7B	107.8	C10—C11—H11	120.0
C1—C7—P1	112.58 (17)	C10—C11—C12	120.1 (3)
C1—C7—H7A	109.1	C12—C11—H11	120.0
C1—C7—H7B	109.1	C15—C16—H16	119.9
C13—C8—P1	118.1 (2)	C17—C16—C15	120.2 (3)
C9—C8—P1	122.10 (19)	C17—C16—H16	119.9
C9—C8—C13	119.8 (2)	C18—C17—H17	119.9
C25—C24—H24	120.0	C16—C17—C18	120.2 (2)
C23—C24—H24	120.0	C16—C17—H17	119.9
C23—C24—C25	119.9 (3)	C8—C9—H9	120.0
C4—C3—H3	120.0	C10—C9—C8	119.9 (2)
C2—C3—H3	120.0	C10—C9—H9	120.0
C2—C3—C4	120.1 (3)	C21—C22—H22	119.8
C8—C13—H13	120.4	C23—C22—H22	119.8
C12—C13—C8	119.3 (3)	C23—C22—C21	120.4 (3)
C12—C13—H13	120.4	C24—C25—C20	119.5 (3)
C25—C20—P1	118.2 (2)	C24—C25—H25	120.3
C21—C20—P1	121.4 (2)	C20—C25—H25	120.3
C21—C20—C25	120.3 (2)	C13—C12—C11	120.3 (3)
C6—C5—H5	119.8	C13—C12—H12	119.8
C4—C5—H5	119.8	C11—C12—H12	119.8
C4—C5—C6	120.5 (2)	C20—C21—C22	119.4 (3)
C5—C6—H6	120.2	C20—C21—H21	120.3
C1—C6—C5	119.6 (2)	C22—C21—H21	120.3
C1—C6—H6	120.2	C3—C2—C1	120.3 (2)
C3—C4—H4	120.1	C3—C2—H2	119.9
C5—C4—C3	119.8 (3)	C1—C2—H2	119.9
C5—C4—H4	120.1	C24—C23—H23	119.8
C14—C15—H15	120.2	C22—C23—C24	120.4 (3)
C14—C15—C16	119.7 (2)	C22—C23—H23	119.8
C16—C15—H15	120.2	H1A—O1—H1B	109.5
C15—C14—P1	119.93 (19)
P1—C7—C1—C6	94.1 (3)	C6—C5—C4—C3	−0.3 (4)
P1—C7—C1—C2	−86.2 (3)	C6—C1—C2—C3	−0.9 (4)
P1—C8—C13—C12	−179.3 (2)	C4—C3—C2—C1	1.4 (4)
P1—C8—C9—C10	178.5 (2)	C4—C5—C6—C1	0.8 (4)
P1—C20—C25—C24	177.77 (19)	C15—C14—C19—C18	−1.6 (4)
P1—C20—C21—C22	−177.8 (2)	C15—C16—C17—C18	−0.5 (5)
P1—C14—C19—C18	−178.0 (2)	C14—P1—C7—C1	−54.7 (2)
C7—P1—C8—C13	44.1 (2)	C14—P1—C8—C13	164.6 (2)
C7—P1—C8—C9	−135.8 (2)	C14—P1—C8—C9	−15.3 (3)
C7—P1—C20—C25	−156.91 (19)	C14—P1—C20—C25	82.6 (2)
C7—P1—C20—C21	22.1 (2)	C14—P1—C20—C21	−98.4 (2)
C7—P1—C14—C15	−102.9 (2)	C14—C15—C16—C17	−0.1 (5)
C7—P1—C14—C19	73.5 (2)	C19—C18—C17—C16	0.1 (4)
C7—C1—C2—C3	179.4 (2)	C10—C11—C12—C13	−1.2 (5)
C8—P1—C7—C1	65.5 (2)	C11—C10—C9—C8	0.9 (4)
C8—P1—C20—C25	−37.5 (2)	C16—C15—C14—P1	177.6 (2)
C8—P1—C20—C21	141.5 (2)	C16—C15—C14—C19	1.2 (4)
C8—P1—C14—C15	136.6 (2)	C17—C18—C19—C14	1.0 (4)
C8—P1—C14—C19	−47.0 (2)	C9—C8—C13—C12	0.7 (4)
C8—C13—C12—C11	0.6 (4)	C9—C10—C11—C12	0.4 (4)
C13—C8—C9—C10	−1.4 (4)	C25—C24—C23—C22	1.1 (4)
C20—P1—C7—C1	−175.62 (17)	C25—C20—C21—C22	1.2 (4)
C20—P1—C8—C13	−74.5 (2)	C21—C20—C25—C24	−1.3 (4)
C20—P1—C8—C9	105.5 (2)	C21—C22—C23—C24	−1.1 (4)
C20—P1—C14—C15	16.8 (3)	C2—C3—C4—C5	−0.8 (4)
C20—P1—C14—C19	−166.8 (2)	C23—C24—C25—C20	0.1 (4)
C5—C6—C1—C7	179.6 (2)	C23—C22—C21—C20	0.0 (4)
C5—C6—C1—C2	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Cl1i	0.85	2.27	3.114 (3)	170
C7—H7A···Cl1	0.97	2.57	3.511 (3)	162
C7—H7B···Cl1ii	0.97	2.60	3.528 (2)	160
C12—H12···O1iii	0.93	2.47	3.207 (5)	136
C17—H17···Cl1iv	0.93	2.81	3.562 (3)	139
C3—H3···Cg4v	0.93	2.83	3.584 (3)	139
C18—H18···Cg2vi	0.93	2.98	3.720 (3)	137

Table 1

Hydrogen-bond geometry (, )

Cg2 and Cg4 are the centroids of rings C8-C13 and C20-C25, respectively.

DHA	DH	HA	D A	DHA
O1H1BCl1i	0.85	2.27	3.114(3)	170
C7H7ACl1	0.97	2.57	3.511(3)	162
C7H7BCl1ii	0.97	2.60	3.528(2)	160
C12H12O1iii	0.93	2.47	3.207(5)	136
C17H17Cl1iv	0.93	2.81	3.562(3)	139
C3H3Cg4v	0.93	2.83	3.584(3)	139
C18H18Cg2vi	0.93	2.98	3.720(3)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .