Bis(triphenyl-phosphanyl-idene)iminium dichloridotriphenyl-stannate(IV).

The structure of the title compound, [Ph(3)P=N=PPh(3)](+)[Ph(3)SnCl(2)](-) or (C(36)H(30)NP(2))[Sn(C(6)H(5))(3)Cl(2)], obtained as a by product of the reaction between Ph(3)SnCl and [Ph(3)P=N=PPh(3)](+)·HSeO(3) (-), consists of discrete essentially isolated ions. Both the cation and the anion lie on twofold axes which pass through the central N atom in the cation and through the Sn(IV) atom in the anion. In the crystal, the ions inter-act only through a weak inter-action between the Cl atom of the anion and an H atom of a phenyl ring of the cation.

Related literature

For general background to selenite compounds, see: Delferro et al. (2010 ▶, 2011 ▶). For related structures, see: Harrison et al. (1978 ▶); Nayek et al. (2010 ▶); Ng (1995 ▶, 1999 ▶). For details of the Cambridge Crystal Structure Database, see: Allen (2002 ▶).

Experimental

Crystal data

(C36H30NP2)[Sn(C6H5)3Cl2]

M = 959.44

Orthorhombic,

a = 17.9119 (6) Å

b = 9.7744 (3) Å

c = 13.3835 (4) Å

V = 2343.16 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.76 mm−1

T = 296 K

0.42 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.629, T max = 0.746

36432 measured reflections

7179 independent reflections

6352 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.04

7179 reflections

273 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 3430 Friedel pairs

Flack parameter: −0.022 (13)

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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035422/su2296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035422/su2296Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035422/su2296Isup3.mol

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

(C36H30NP2)[Sn(C6H5)3Cl2]	F(000) = 980
Mr = 959.44	Dx = 1.360 Mg m−3
Orthorhombic, Pnn2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 -2n	Cell parameters from 999 reflections
a = 17.9119 (6) Å	θ = 3–27°
b = 9.7744 (3) Å	µ = 0.76 mm−1
c = 13.3835 (4) Å	T = 296 K
V = 2343.16 (13) Å3	Prism, colourless
Z = 2	0.42 × 0.22 × 0.18 mm

Bruker APEXII CCD diffractometer	7179 independent reflections
Radiation source: fine-focus sealed tube	6352 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 30.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −25→25
Tmin = 0.629, Tmax = 0.746	k = −13→13
36432 measured reflections	l = −19→19

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)] = 0.025	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.062P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
7179 reflections	Δρmax = 0.20 e Å−3
273 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 3430 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.022 (13)

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
C1	0.88435 (9)	0.69033 (16)	0.54090 (12)	0.0432 (3)
C2	0.81206 (10)	0.72511 (17)	0.51192 (17)	0.0576 (5)
H2	0.7811	0.6596	0.4832	0.069*
C3	0.78656 (12)	0.8566 (2)	0.5259 (2)	0.0726 (6)
H3	0.7384	0.8800	0.5065	0.087*
C4	0.83185 (16)	0.9526 (2)	0.5683 (2)	0.0786 (7)
H4	0.8146	1.0416	0.5764	0.094*
C5	0.90228 (15)	0.9193 (2)	0.5988 (2)	0.0812 (7)
H5	0.9323	0.9852	0.6287	0.097*
C6	0.92925 (11)	0.7871 (2)	0.58522 (17)	0.0611 (5)
H6	0.9772	0.7643	0.6059	0.073*
C7	0.85781 (9)	0.40724 (16)	0.59273 (12)	0.0436 (3)
C8	0.88264 (11)	0.3604 (2)	0.68448 (15)	0.0542 (4)
H8	0.9306	0.3818	0.7060	0.065*
C9	0.83627 (14)	0.2816 (2)	0.74452 (16)	0.0677 (5)
H9	0.8530	0.2500	0.8061	0.081*
C10	0.76534 (13)	0.2506 (2)	0.71193 (19)	0.0711 (6)
H10	0.7339	0.1989	0.7524	0.085*
C11	0.74047 (11)	0.2948 (2)	0.62107 (19)	0.0660 (6)
H11	0.6928	0.2713	0.5995	0.079*
C12	0.78589 (9)	0.37442 (19)	0.56092 (16)	0.0537 (4)
H12	0.7685	0.4059	0.4996	0.064*
C13	0.90382 (10)	0.48460 (16)	0.39035 (14)	0.0428 (3)
C14	0.91498 (10)	0.5907 (2)	0.32243 (14)	0.0507 (4)
H14	0.9251	0.6784	0.3456	0.061*
C15	0.91117 (12)	0.5664 (3)	0.22073 (16)	0.0654 (5)
H15	0.9192	0.6376	0.1758	0.078*
C16	0.89552 (13)	0.4373 (3)	0.18605 (18)	0.0725 (6)
H16	0.8922	0.4215	0.1177	0.087*
C17	0.88481 (14)	0.3321 (3)	0.2517 (2)	0.0783 (7)
H17	0.8744	0.2450	0.2273	0.094*
C18	0.88920 (11)	0.3529 (2)	0.35474 (17)	0.0601 (5)
H18	0.8825	0.2804	0.3989	0.072*
C19	0.93324 (11)	0.8460 (2)	0.92452 (14)	0.0555 (4)
C20	0.94493 (15)	0.7072 (2)	0.9444 (2)	0.0787 (6)
H20	0.9844	0.6807	0.9852	0.094*
C21	0.89793 (18)	0.6079 (3)	0.9033 (3)	0.0981 (8)
H21	0.9064	0.5160	0.9172	0.118*
C22	0.84039 (17)	0.6437 (3)	0.8437 (2)	0.0908 (8)
H22	0.8097	0.5766	0.8166	0.109*
C23	0.82711 (15)	0.7791 (3)	0.82299 (19)	0.0835 (7)
H23	0.7874	0.8035	0.7819	0.100*
C24	0.87280 (12)	0.8799 (2)	0.86322 (17)	0.0681 (5)
H24	0.8630	0.9714	0.8492	0.082*
C25	1.0000	1.0000	1.1555 (2)	0.0497 (6)
C26	1.06462 (16)	1.0253 (2)	1.20891 (19)	0.0680 (6)
H26	1.1092	1.0408	1.1752	0.082*
C27	1.0633 (2)	1.0278 (3)	1.3133 (2)	0.0940 (11)
H27	1.1066	1.0488	1.3484	0.113*
C28	1.0000	1.0000	1.3635 (3)	0.104 (2)
H28	1.0000	1.0000	1.4329	0.125*
N1	1.0000	0.5000	0.55925 (18)	0.0477 (5)
P1	0.91740 (2)	0.51807 (4)	0.52080 (3)	0.03734 (9)
Sn1	1.0000	1.0000	0.996036 (19)	0.04870 (5)
Cl1	0.88562 (3)	1.16132 (5)	0.99969 (5)	0.07087 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (8)	0.0429 (7)	0.0452 (8)	−0.0004 (6)	0.0109 (6)	−0.0061 (6)
C2	0.0472 (8)	0.0522 (8)	0.0735 (14)	0.0078 (6)	0.0013 (9)	−0.0093 (10)
C3	0.0606 (11)	0.0593 (11)	0.0979 (19)	0.0178 (9)	0.0169 (11)	−0.0040 (11)
C4	0.0870 (17)	0.0482 (10)	0.1007 (18)	0.0135 (11)	0.0296 (14)	−0.0106 (11)
C5	0.0852 (16)	0.0531 (12)	0.105 (2)	−0.0121 (11)	0.0140 (14)	−0.0259 (12)
C6	0.0527 (10)	0.0546 (10)	0.0760 (13)	−0.0077 (8)	0.0047 (9)	−0.0150 (9)
C7	0.0381 (7)	0.0415 (7)	0.0513 (9)	−0.0010 (6)	0.0064 (7)	−0.0023 (7)
C8	0.0569 (11)	0.0566 (10)	0.0490 (10)	−0.0034 (8)	0.0032 (8)	−0.0030 (8)
C9	0.0928 (16)	0.0613 (11)	0.0491 (10)	−0.0055 (10)	0.0154 (10)	0.0016 (9)
C10	0.0732 (14)	0.0598 (12)	0.0802 (15)	−0.0155 (10)	0.0313 (12)	−0.0049 (10)
C11	0.0459 (10)	0.0605 (11)	0.0914 (16)	−0.0101 (8)	0.0166 (10)	−0.0056 (11)
C12	0.0390 (8)	0.0516 (10)	0.0703 (12)	−0.0042 (7)	0.0018 (8)	0.0020 (8)
C13	0.0355 (7)	0.0512 (9)	0.0418 (9)	0.0077 (6)	−0.0030 (6)	−0.0088 (6)
C14	0.0497 (9)	0.0579 (9)	0.0445 (9)	0.0199 (7)	−0.0037 (7)	0.0002 (7)
C15	0.0618 (11)	0.0859 (15)	0.0484 (10)	0.0300 (11)	−0.0056 (9)	0.0042 (10)
C16	0.0651 (13)	0.1060 (18)	0.0464 (11)	0.0206 (13)	−0.0085 (9)	−0.0204 (13)
C17	0.0743 (14)	0.0871 (17)	0.0736 (16)	−0.0019 (12)	0.0025 (12)	−0.0441 (14)
C18	0.0597 (11)	0.0558 (11)	0.0648 (13)	−0.0010 (8)	0.0035 (9)	−0.0120 (9)
C19	0.0593 (11)	0.0659 (11)	0.0414 (9)	0.0071 (8)	0.0049 (8)	−0.0087 (8)
C20	0.0872 (16)	0.0715 (13)	0.0774 (15)	0.0129 (12)	−0.0088 (12)	−0.0081 (11)
C21	0.113 (2)	0.0713 (16)	0.110 (2)	−0.0072 (15)	−0.0013 (18)	−0.0146 (16)
C22	0.0943 (19)	0.0950 (19)	0.0831 (18)	−0.0156 (15)	0.0095 (15)	−0.0308 (14)
C23	0.0711 (15)	0.114 (2)	0.0650 (14)	0.0008 (14)	−0.0075 (11)	−0.0255 (14)
C24	0.0700 (13)	0.0775 (13)	0.0567 (11)	0.0032 (10)	−0.0080 (9)	−0.0113 (10)
C25	0.0626 (16)	0.0476 (13)	0.0389 (13)	−0.0052 (10)	0.000	0.000
C26	0.0810 (15)	0.0662 (11)	0.0568 (13)	−0.0148 (10)	−0.0186 (11)	0.0072 (9)
C27	0.152 (3)	0.0699 (14)	0.0604 (16)	−0.0191 (16)	−0.0434 (19)	0.0006 (12)
C28	0.210 (7)	0.064 (2)	0.0396 (17)	−0.012 (2)	0.000	0.000
N1	0.0341 (9)	0.0663 (13)	0.0427 (11)	0.0008 (8)	0.000	0.000
P1	0.03077 (16)	0.04225 (16)	0.0390 (2)	0.00106 (13)	0.00104 (13)	−0.00220 (15)
Sn1	0.04949 (8)	0.06206 (9)	0.03456 (7)	0.00872 (6)	0.000	0.000
Cl1	0.0614 (2)	0.0894 (3)	0.0618 (3)	0.0292 (2)	−0.0110 (3)	−0.0201 (3)

C1—C6	1.376 (2)	C16—C17	1.367 (4)
C1—C2	1.394 (2)	C16—H16	0.9300
C1—P1	1.8049 (16)	C17—C18	1.396 (4)
C2—C3	1.377 (2)	C17—H17	0.9300
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.364 (4)	C19—C24	1.398 (3)
C3—H3	0.9300	C19—C20	1.398 (3)
C4—C5	1.365 (4)	C19—Sn1	2.1476 (19)
C4—H4	0.9300	C20—C21	1.397 (4)
C5—C6	1.391 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.349 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.384 (3)	C22—C23	1.373 (4)
C7—C12	1.394 (2)	C22—H22	0.9300
C7—P1	1.7998 (16)	C23—C24	1.389 (3)
C8—C9	1.389 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.377 (3)	C25—C26i	1.383 (3)
C9—H9	0.9300	C25—C26	1.383 (3)
C10—C11	1.365 (4)	C25—Sn1	2.134 (3)
C10—H10	0.9300	C26—C27	1.397 (4)
C11—C12	1.384 (3)	C26—H26	0.9300
C11—H11	0.9300	C27—C28	1.346 (5)
C12—H12	0.9300	C27—H27	0.9300
C13—C18	1.398 (3)	C28—C27i	1.345 (5)
C13—C14	1.393 (3)	C28—H28	0.9300
C13—P1	1.7929 (19)	N1—P1ii	1.5763 (9)
C14—C15	1.383 (3)	N1—P1	1.5763 (9)
C14—H14	0.9300	Sn1—C19i	2.1476 (19)
C15—C16	1.374 (4)	Sn1—Cl1	2.5858 (4)
C15—H15	0.9300	Sn1—Cl1i	2.5858 (4)
C6—C1—C2	119.70 (16)	C17—C18—C13	118.8 (2)
C6—C1—P1	120.91 (14)	C17—C18—H18	120.6
C2—C1—P1	119.39 (12)	C13—C18—H18	120.6
C1—C2—C3	119.87 (18)	C24—C19—C20	117.2 (2)
C1—C2—H2	120.1	C24—C19—Sn1	121.74 (16)
C3—C2—H2	120.1	C20—C19—Sn1	120.81 (16)
C4—C3—C2	120.1 (2)	C21—C20—C19	120.6 (3)
C4—C3—H3	120.0	C21—C20—H20	119.7
C2—C3—H3	120.0	C19—C20—H20	119.7
C5—C4—C3	120.7 (2)	C22—C21—C20	120.8 (3)
C5—C4—H4	119.7	C22—C21—H21	119.6
C3—C4—H4	119.7	C20—C21—H21	119.6
C4—C5—C6	120.2 (2)	C23—C22—C21	120.1 (3)
C4—C5—H5	119.9	C23—C22—H22	119.9
C6—C5—H5	119.9	C21—C22—H22	119.9
C1—C6—C5	119.4 (2)	C22—C23—C24	120.2 (3)
C1—C6—H6	120.3	C22—C23—H23	119.9
C5—C6—H6	120.3	C24—C23—H23	119.9
C8—C7—C12	119.46 (16)	C19—C24—C23	121.0 (2)
C8—C7—P1	118.89 (13)	C19—C24—H24	119.5
C12—C7—P1	121.54 (14)	C23—C24—H24	119.5
C7—C8—C9	120.3 (2)	C26i—C25—C26	117.7 (3)
C7—C8—H8	119.8	C26i—C25—Sn1	121.14 (16)
C9—C8—H8	119.8	C26—C25—Sn1	121.14 (16)
C8—C9—C10	119.4 (2)	C25—C26—C27	120.4 (3)
C8—C9—H9	120.3	C25—C26—H26	119.8
C10—C9—H9	120.3	C27—C26—H26	119.8
C11—C10—C9	120.91 (19)	C28—C27—C26	120.6 (3)
C11—C10—H10	119.5	C28—C27—H27	119.7
C9—C10—H10	119.5	C26—C27—H27	119.7
C10—C11—C12	120.3 (2)	C27i—C28—C27	120.1 (4)
C10—C11—H11	119.9	C27i—C28—H28	119.9
C12—C11—H11	119.9	C27—C28—H28	119.9
C11—C12—C7	119.66 (19)	P1ii—N1—P1	141.90 (17)
C11—C12—H12	120.2	N1—P1—C13	115.13 (10)
C7—C12—H12	120.2	N1—P1—C7	108.34 (8)
C18—C13—C14	119.33 (18)	C13—P1—C7	109.30 (8)
C18—C13—P1	121.71 (15)	N1—P1—C1	111.33 (6)
C14—C13—P1	118.69 (13)	C13—P1—C1	105.72 (8)
C15—C14—C13	120.5 (2)	C7—P1—C1	106.69 (7)
C15—C14—H14	119.8	C25—Sn1—C19i	116.46 (5)
C13—C14—H14	119.8	C25—Sn1—C19	116.46 (5)
C16—C15—C14	120.0 (2)	C19i—Sn1—C19	127.07 (10)
C16—C15—H15	120.0	C25—Sn1—Cl1	88.916 (18)
C14—C15—H15	120.0	C19i—Sn1—Cl1	91.27 (5)
C17—C16—C15	120.2 (2)	C19—Sn1—Cl1	89.70 (5)
C17—C16—H16	119.9	C25—Sn1—Cl1i	88.917 (18)
C15—C16—H16	119.9	C19i—Sn1—Cl1i	89.70 (5)
C16—C17—C18	121.2 (2)	C19—Sn1—Cl1i	91.27 (5)
C16—C17—H17	119.4	Cl1—Sn1—Cl1i	177.83 (4)
C18—C17—H17	119.4

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cl1iii	0.93	2.79	3.718 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cl1i	0.93	2.79	3.718 (2)	173

Symmetry code: (i) .