Bis(triphenyl-λ-phosphanylidene)ammonium hydrogen dichloride.

In the title compound, [(Ph(3)P)(2)N](+)·[Cl-H-Cl](-) or C(36)H(30)NP(2) (+)·Cl(2)H(-), the H atom of the [Cl-H-Cl](-) anion and the N atom of the [(Ph(3)P)(2)N](+) cation are located on a twofold axis, yielding overall symmetry 2 for both the cation and the anion. The central P-N-P angle [144.12 (13)°] of the cation is in the expected range and indicates only weak cation-anion inter-actions. The almost linear [Cl-H-Cl](-) anion is a rare example of a symmetric hydrogen bridge in a hydrogen dichloride anion. The Cl⋯Cl distance and two equal Cl-H bonds are typical of such a symmetric hydrogen dichloride anion.

Related literature

For selected examples containing the [Cl—H—Cl]− anion, see: Atwood et al. (1990 ▶); Mootz et al. (1981 ▶); Habtemariam et al. (2001 ▶); Swann et al. (1984 ▶); Neumüller et al. (2005 ▶). For other bis(triphenyl-λ5-phosphanylidene)ammonium halide structures, see: Knapp & Uzun (2010 ▶); Beckett et al. (2010 ▶). For a discussion of the [(Ph3P)2N]+ cation, see: Lewis & Dance (2000 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the synthesis of [(Ph3P)2N]Cl, see: Ruff & Schlientz (1974 ▶).

Experimental

Crystal data

C36H30NP2 +·Cl2H−

M = 610.46

Orthorhombic,

a = 11.6467 (3) Å

b = 16.5474 (4) Å

c = 15.7584 (3) Å

V = 3037.00 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.18 × 0.14 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.940, T max = 0.970

28633 measured reflections

2994 independent reflections

2671 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.08

2994 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.79 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2011 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035057/su2304sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035057/su2304Isup2.hkl

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

C36H30NP2+·Cl2H−	F(000) = 1272
Mr = 610.46	Dx = 1.335 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9956 reflections
a = 11.6467 (3) Å	θ = 2.5–30.8°
b = 16.5474 (4) Å	µ = 0.35 mm−1
c = 15.7584 (3) Å	T = 100 K
V = 3037.00 (12) Å3	Block, colourless
Z = 4	0.18 × 0.14 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	2994 independent reflections
Radiation source: microfocus sealed tube	2671 reflections with I > 2σ(I)
multilayer mirro optics	Rint = 0.030
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.940, Tmax = 0.970	k = −19→20
28633 measured reflections	l = −19→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0372P)2 + 2.5322P] where P = (Fo2 + 2Fc2)/3
2994 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.79 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.

	x	y	z	Uiso*/Ueq
P1	0.37492 (3)	0.47726 (2)	0.22743 (2)	0.01086 (11)
N1	0.5000	0.44792 (11)	0.2500	0.0142 (4)
C1	0.32847 (13)	0.42600 (9)	0.13289 (10)	0.0136 (3)
C2	0.37451 (13)	0.35003 (10)	0.11482 (10)	0.0163 (3)
H2	0.4320	0.3275	0.1505	0.0226 (13)*
C3	0.33594 (15)	0.30750 (10)	0.04441 (11)	0.0203 (4)
H3	0.3678	0.2561	0.0315	0.0226 (13)*
C4	0.25109 (16)	0.33988 (10)	−0.00703 (11)	0.0227 (4)
H4	0.2247	0.3104	−0.0549	0.0226 (13)*
C5	0.20431 (15)	0.41512 (11)	0.01091 (11)	0.0224 (4)
H5	0.1460	0.4369	−0.0245	0.0226 (13)*
C6	0.24288 (14)	0.45863 (10)	0.08092 (10)	0.0173 (3)
H6	0.2112	0.5102	0.0933	0.0226 (13)*
C7	0.36204 (12)	0.58392 (9)	0.20936 (10)	0.0126 (3)
C8	0.43189 (13)	0.61829 (10)	0.14660 (10)	0.0171 (3)
H8	0.4784	0.5847	0.1118	0.0226 (13)*
C9	0.43306 (14)	0.70100 (10)	0.13533 (11)	0.0203 (4)
H9	0.4809	0.7243	0.0931	0.0226 (13)*
C10	0.36455 (14)	0.75028 (10)	0.18551 (11)	0.0204 (4)
H10	0.3661	0.8072	0.1778	0.0226 (13)*
C11	0.29393 (15)	0.71670 (10)	0.24675 (11)	0.0210 (4)
H11	0.2462	0.7505	0.2803	0.0226 (13)*
C12	0.29273 (14)	0.63361 (10)	0.25912 (10)	0.0169 (3)
H12	0.2447	0.6107	0.3015	0.0226 (13)*
C13	0.27637 (13)	0.44720 (9)	0.30980 (10)	0.0128 (3)
C14	0.15825 (13)	0.45901 (10)	0.30003 (10)	0.0162 (3)
H14	0.1295	0.4861	0.2513	0.0226 (13)*
C15	0.08307 (14)	0.43109 (10)	0.36169 (11)	0.0189 (3)
H15	0.0028	0.4391	0.3550	0.0226 (13)*
C16	0.12438 (14)	0.39159 (10)	0.43294 (10)	0.0179 (3)
H16	0.0724	0.3723	0.4748	0.0226 (13)*
C17	0.24172 (14)	0.38023 (10)	0.44327 (10)	0.0174 (3)
H17	0.2700	0.3534	0.4923	0.0226 (13)*
C18	0.31776 (13)	0.40806 (9)	0.38184 (10)	0.0149 (3)
H18	0.3980	0.4004	0.3890	0.0226 (13)*
Cl1	0.49306 (4)	0.14372 (3)	0.15163 (3)	0.03665 (15)
H1	0.5000	0.149 (3)	0.2500	0.087 (15)*

	U11	U22	U33	U12	U13	U23
P1	0.0108 (2)	0.0097 (2)	0.0120 (2)	−0.00044 (14)	−0.00017 (14)	−0.00049 (14)
N1	0.0123 (9)	0.0108 (9)	0.0196 (10)	0.000	−0.0001 (7)	0.000
C1	0.0144 (7)	0.0138 (8)	0.0127 (7)	−0.0053 (6)	0.0026 (6)	−0.0011 (6)
C2	0.0148 (7)	0.0154 (8)	0.0188 (8)	−0.0027 (6)	0.0026 (6)	−0.0021 (6)
C3	0.0231 (8)	0.0158 (8)	0.0219 (9)	−0.0040 (7)	0.0065 (7)	−0.0059 (7)
C4	0.0334 (9)	0.0200 (9)	0.0146 (8)	−0.0099 (7)	0.0004 (7)	−0.0030 (7)
C5	0.0300 (9)	0.0212 (9)	0.0160 (8)	−0.0063 (7)	−0.0066 (7)	0.0041 (7)
C6	0.0229 (8)	0.0135 (8)	0.0155 (8)	−0.0021 (6)	−0.0011 (6)	0.0015 (6)
C7	0.0126 (7)	0.0118 (7)	0.0134 (7)	0.0000 (6)	−0.0044 (6)	−0.0001 (6)
C8	0.0160 (7)	0.0169 (8)	0.0184 (8)	0.0015 (6)	0.0007 (6)	0.0006 (6)
C9	0.0187 (8)	0.0174 (9)	0.0247 (9)	−0.0021 (7)	−0.0007 (7)	0.0067 (7)
C10	0.0218 (8)	0.0118 (8)	0.0276 (9)	0.0007 (6)	−0.0076 (7)	0.0019 (7)
C11	0.0231 (8)	0.0158 (8)	0.0240 (9)	0.0054 (7)	−0.0021 (7)	−0.0027 (7)
C12	0.0173 (8)	0.0166 (8)	0.0169 (8)	0.0019 (6)	0.0003 (6)	0.0001 (6)
C13	0.0148 (7)	0.0106 (7)	0.0130 (8)	−0.0014 (6)	0.0006 (6)	−0.0023 (6)
C14	0.0155 (7)	0.0185 (8)	0.0147 (8)	−0.0014 (6)	−0.0018 (6)	0.0002 (6)
C15	0.0133 (7)	0.0214 (9)	0.0219 (9)	−0.0024 (6)	0.0001 (6)	−0.0006 (7)
C16	0.0202 (8)	0.0153 (8)	0.0180 (8)	−0.0039 (6)	0.0047 (6)	0.0001 (6)
C17	0.0230 (8)	0.0142 (8)	0.0149 (8)	0.0002 (6)	−0.0009 (6)	0.0022 (6)
C18	0.0151 (7)	0.0127 (8)	0.0168 (8)	0.0008 (6)	−0.0009 (6)	−0.0005 (6)
Cl1	0.0363 (3)	0.0556 (3)	0.0181 (2)	0.0236 (2)	−0.00128 (18)	−0.0032 (2)

P1—N1	1.5762 (7)	C9—C10	1.388 (2)
P1—C7	1.7940 (16)	C9—H9	0.9500
P1—C1	1.7976 (16)	C10—C11	1.384 (2)
P1—C13	1.8028 (15)	C10—H10	0.9500
N1—P1i	1.5761 (7)	C11—C12	1.389 (2)
C1—C2	1.396 (2)	C11—H11	0.9500
C1—C6	1.399 (2)	C12—H12	0.9500
C2—C3	1.389 (2)	C13—C18	1.393 (2)
C2—H2	0.9500	C13—C14	1.398 (2)
C3—C4	1.386 (3)	C14—C15	1.387 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.388 (3)	C15—C16	1.386 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.392 (2)	C16—C17	1.389 (2)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.390 (2)
C7—C12	1.394 (2)	C17—H17	0.9500
C7—C8	1.401 (2)	C18—H18	0.9500
C8—C9	1.380 (2)	Cl1—H1	1.555 (3)
C8—H8	0.9500
N1—P1—C7	114.59 (8)	C8—C9—C10	120.24 (16)
N1—P1—C1	108.65 (7)	C8—C9—H9	119.9
C7—P1—C1	107.91 (7)	C10—C9—H9	119.9
N1—P1—C13	109.93 (6)	C11—C10—C9	120.19 (15)
C7—P1—C13	109.42 (7)	C11—C10—H10	119.9
C1—P1—C13	105.96 (7)	C9—C10—H10	119.9
P1i—N1—P1	144.12 (13)	C10—C11—C12	120.08 (16)
C2—C1—C6	120.13 (14)	C10—C11—H11	120.0
C2—C1—P1	118.58 (12)	C12—C11—H11	120.0
C6—C1—P1	121.17 (12)	C11—C12—C7	119.95 (16)
C3—C2—C1	119.67 (15)	C11—C12—H12	120.0
C3—C2—H2	120.2	C7—C12—H12	120.0
C1—C2—H2	120.2	C18—C13—C14	119.68 (14)
C4—C3—C2	120.14 (16)	C18—C13—P1	119.66 (11)
C4—C3—H3	119.9	C14—C13—P1	120.57 (12)
C2—C3—H3	119.9	C15—C14—C13	119.84 (15)
C3—C4—C5	120.49 (16)	C15—C14—H14	120.1
C3—C4—H4	119.8	C13—C14—H14	120.1
C5—C4—H4	119.8	C16—C15—C14	120.37 (15)
C4—C5—C6	119.92 (16)	C16—C15—H15	119.8
C4—C5—H5	120.0	C14—C15—H15	119.8
C6—C5—H5	120.0	C15—C16—C17	120.03 (15)
C5—C6—C1	119.63 (16)	C15—C16—H16	120.0
C5—C6—H6	120.2	C17—C16—H16	120.0
C1—C6—H6	120.2	C16—C17—C18	120.02 (15)
C12—C7—C8	119.59 (15)	C16—C17—H17	120.0
C12—C7—P1	122.65 (12)	C18—C17—H17	120.0
C8—C7—P1	117.57 (12)	C17—C18—C13	120.06 (14)
C9—C8—C7	119.94 (15)	C17—C18—H18	120.0
C9—C8—H8	120.0	C13—C18—H18	120.0
C7—C8—H8	120.0
C7—P1—N1—P1i	8.50 (6)	C12—C7—C8—C9	1.0 (2)
C1—P1—N1—P1i	129.26 (6)	P1—C7—C8—C9	−174.15 (13)
C13—P1—N1—P1i	−115.21 (6)	C7—C8—C9—C10	−0.5 (2)
N1—P1—C1—C2	27.31 (14)	C8—C9—C10—C11	−0.5 (3)
C7—P1—C1—C2	152.11 (12)	C9—C10—C11—C12	1.0 (3)
C13—P1—C1—C2	−90.78 (13)	C10—C11—C12—C7	−0.5 (2)
N1—P1—C1—C6	−156.65 (13)	C8—C7—C12—C11	−0.5 (2)
C7—P1—C1—C6	−31.85 (15)	P1—C7—C12—C11	174.41 (13)
C13—P1—C1—C6	85.26 (14)	N1—P1—C13—C18	3.27 (15)
C6—C1—C2—C3	0.8 (2)	C7—P1—C13—C18	−123.40 (13)
P1—C1—C2—C3	176.89 (12)	C1—P1—C13—C18	120.50 (13)
C1—C2—C3—C4	−0.8 (2)	N1—P1—C13—C14	−173.36 (13)
C2—C3—C4—C5	0.4 (3)	C7—P1—C13—C14	59.97 (14)
C3—C4—C5—C6	0.2 (3)	C1—P1—C13—C14	−56.13 (14)
C4—C5—C6—C1	−0.2 (2)	C18—C13—C14—C15	−0.6 (2)
C2—C1—C6—C5	−0.3 (2)	P1—C13—C14—C15	176.07 (12)
P1—C1—C6—C5	−176.29 (12)	C13—C14—C15—C16	0.0 (2)
N1—P1—C7—C12	−118.52 (12)	C14—C15—C16—C17	0.4 (3)
C1—P1—C7—C12	120.31 (13)	C15—C16—C17—C18	−0.4 (2)
C13—P1—C7—C12	5.46 (15)	C16—C17—C18—C13	−0.1 (2)
N1—P1—C7—C8	56.51 (13)	C14—C13—C18—C17	0.6 (2)
C1—P1—C7—C8	−64.66 (13)	P1—C13—C18—C17	−176.05 (12)
C13—P1—C7—C8	−179.52 (12)

D—H···A	D—H	H···A	D···A	D—H···A
Cl1—H1···Cl1i	1.56 (1)	1.56 (1)	3.1045 (9)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
Cl1—H1⋯Cl1i	1.56 (1)	1.56 (1)	3.1045 (9)	173 (3)

Symmetry code: (i) .