Bis(triphenyl­phosphanyl­idene)iminium dichloridotriphenyl­stannate(IV)

De Lorentiis, L.; Graiff, C.; Predieri, G.

doi:10.1107/S1600536811035422

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1356

https://doi.org/10.1107/S1600536811035422

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Bis(triphenylphosphanylidene)iminium dichloridotriphenylstannate(IV)

Lucio De Lorentiis,^a Claudia Graiff ^a ^* and Giovanni Predieri ^a

^aDipartimento di Chimica GIAF, Viale delle Scienze, 17/A, Università di Parma, 43100 Parma, Italy
^*Correspondence e-mail: claudia.graiff@unipr.it

(Received 14 July 2011; accepted 30 August 2011; online 14 September 2011)

The structure of the title compound, [Ph₃P=N=PPh₃]⁺[Ph₃SnCl₂]⁻ or (C₃₆H₃₀NP₂)[Sn(C₆H₅)₃Cl₂], obtained as a by product of the reaction between Ph₃SnCl and [Ph₃P=N=PPh₃]⁺·HSeO₃⁻, 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 interact only through a weak interaction 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_r = 959.44
Orthorhombic, P n n 2
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.065
S = 1.04
7179 reflections
273 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 3430 Friedel pairs
Flack parameter: −0.022 (13)

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) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035422/su2296sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035422/su2296Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035422/su2296Isup3.mol

checkCIF report

Comment top

The title compound was isolated from a dichloromethane solution as a by product of the reaction between of Ph₃SnCl with [Ph₃P=N=PPh₃]⁺ HSeO₃^- in dichloromethane solvent. The hydrogen selenite salt, prepared in the framework of our research activity on selenite compounds (Delferro et al., 2010, Delferro et al., 2011), contained a significant amount of [Ph₃P=N=PPh₃]⁺ Cl^-, which is responsible of the formation of the title compound.

The structure of the title compound consists of discrete [Ph₃P=N=PPh₃]⁺ and [Ph₃SnCl₂]^- ions (Fig. 1). The [Ph₃P=N=PPh₃]⁺, (or PPN⁺ for simplicity), cation is rather typical, lieing on a two fold axis that passes through the central N atom, N1. The P1—N1 bond distance of 1.5763 (9) Å and the P1—N1—P1ⁱ [symmetry code (i) = -x + 2, -y + 1, z] bond angle of 141.9 (2)° are in good agreement with the average values of 1.577 (6) Å and 143 (9)° found in 1409 PPN⁺ cations reported in the Cambridge Crystal Structure Database (CSD, V5.32, last update May 2011; Allen, 2002), see Fig. 3. In particular, examining the 1409 PPN⁺ cations it is evident that less than 40 examples present a linear geometry at the nitrogen atom. On excluding these cases the mean value of the P—N—P bond angle is reduced to 142 (7)°, even more in agreement with the angle in the title compound. The P atom is tetrahedral, with the C—P—C and C—P—N angles averaging 109 (3)°.

The [Ph₃SnCl₂]^- anion exhibits trigonal bipyramidal geometry at the tin atom, with the usual equatorial arrangement of organic groups and the chlorine atoms occupying axial positions. The anion is lying on a two-fold axis passing through the tin atom and atom C25 and C28 of one phenyl ring. The Cl1—Sn1 bond distance is 2.5858 (4) Å and the Cl—Sn—Clⁱⁱ [symmetry code: (ii) = -x + 2, -y + 2, z] bond angle is 177.83 (4)°, both in agreement with the values found in four examples (Ng, 1995,1999; Harrison et al., 1978; Nayek et al., 2010) reported in the CSD: The mean values are 2.590 (2) Å and 176.6 (7)°, respectively. The mean planes of the phenyl rings form dihedral angles of 59.70 (2)° and 38.78 (2)° with the SnC₃ mean plane.

In the crystal there is a weak interaction between the chlorine atom of the dichlorotriphenylstannate anion and a hydrogen atom of a phenyl ring of the bis(triphenylphosphine)iminium cation (Table 1).

Related literature top

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 top

A dichloromethane solution of equimolar amounts of triphenyl-tin chloride and bis(triphenylphosphine)iminium hydrogenselenite was stirred at room temperature for 1 h. The solution was then cooled slowly to 278 K. Crystals suitable for X-ray analysis were obtained from the solution in two days.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. ORTEP drawing of the [Ph₃P=N=PPh₃]⁺ cation, showing the atom labelling and the displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are omitted for clarity. Symmetry code for generating equivalent atoms: ' = -x + 2, -y + 1, z.
	Fig. 2. ORTEP drawing of the [Ph₃SnCl₂]^- anion, showing the atom labelling and the displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are omitted for clarity. Symmetry code for generating equivalent atoms: ' = -x + 2, -y + 2, z.
	Fig. 3. Histogram showing the distribution of the P—N—P bond angle over the 1409 [Ph₃P=N=PPh₃]⁺ cations reported in the Cambridge Structural Database (Allen, 2002).

Bis(triphenylphosphanylidene)iminium dichloridotriphenylstannate(IV) top

Crystal data top

(C₃₆H₃₀NP₂)[Sn(C₆H₅)₃Cl₂]	F(000) = 980
M_r = 959.44	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	7179 independent reflections
Radiation source: fine-focus sealed tube	6352 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 30.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −25→25
T_min = 0.629, T_max = 0.746	k = −13→13
36432 measured reflections	l = −19→19

Refinement top

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(F_o²) + (0.0339P)² + 0.062P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
7179 reflections	Δρ_max = 0.20 e Å⁻³
273 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3430 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.022 (13)

Crystal data top

(C₃₆H₃₀NP₂)[Sn(C₆H₅)₃Cl₂]	V = 2343.16 (13) Å³
M_r = 959.44	Z = 2
Orthorhombic, Pnn2	Mo Kα radiation
a = 17.9119 (6) Å	µ = 0.76 mm⁻¹
b = 9.7744 (3) Å	T = 296 K
c = 13.3835 (4) Å	0.42 × 0.22 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	7179 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	6352 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.746	R_int = 0.026
36432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.20 e Å⁻³
S = 1.04	Δρ_min = −0.25 e Å⁻³
7179 reflections	Absolute structure: Flack (1983), 3430 Friedel pairs
273 parameters	Absolute structure parameter: −0.022 (13)
1 restraint

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	(C₃₆H₃₀NP₂)[Sn(C₆H₅)₃Cl₂]
M_r	959.44
Crystal system, space group	Orthorhombic, Pnn2
Temperature (K)	296
a, b, c (Å)	17.9119 (6), 9.7744 (3), 13.3835 (4)
V (Å³)	2343.16 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.42 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.629, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	36432, 7179, 6352
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.717

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.04
No. of reflections	7179
No. of parameters	273
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25
Absolute structure	Flack (1983), 3430 Friedel pairs
Absolute structure parameter	−0.022 (13)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Acknowledgements

Financial support from the PRIN 2008-Molecular Clusters in Nanoscience and the University of Parma, Italy, is gratefully acknowledged.

References

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