Dimethyl-ammonium dichloridotriphenyl-stannate(IV).

The title salt, [(CH(3))(2)NH(2)][Sn(C(6)H(5))(3)Cl(2)], was obtained as a by-product of the reaction between bis-(dimethyl-ammonium) oxalate and triphenyl-tin chloride. In the stannate anion, the trigonal-bipyramidal coordination environment of the Sn(IV) atom is defined by the phenyl groups in equatorial and the Cl atoms in axial positions. The cations are connected to adjacent anions through N-H⋯Cl and C-H⋯Cl hydrogen-bonding inter-actions, leading to a chain motif parallel to [100].

Related literature

For background to organotin(IV) chemistry, see: Chee et al. (2003 ▶); Evans & Karpel (1985 ▶); Gielen et al. (1995 ▶); Ng & Kumar Das (1997 ▶); Zhang et al. (2006 ▶). For compounds containing the [Sn(C6H5)3Cl2]− ion, see: Harrison et al. (1978 ▶); Ng (1995 ▶, 1999 ▶).

Experimental

Crystal data

(C2H8N)[Sn(C6H5)3Cl2]

M = 466.98

Monoclinic,

a = 7.9865 (1) Å

b = 17.5031 (3) Å

c = 14.9484 (3) Å

β = 105.406 (1)°

V = 2014.53 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.54 mm−1

T = 150 K

0.30 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.656, T max = 0.749

16595 measured reflections

4569 independent reflections

4469 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.045

S = 1.07

4569 reflections

227 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.89 e Å−3

Absolute structure: Flack (1983 ▶), 2256 Friedel pairs

Flack parameter: −0.030 (12)

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028905/wm2636sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028905/wm2636Isup2.hkl

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

(C2H8N)[Sn(C6H5)3Cl2]	F(000) = 936
Mr = 466.98	Dx = 1.540 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 12072 reflections
a = 7.9865 (1) Å	θ = 2.9–27.5°
b = 17.5031 (3) Å	µ = 1.54 mm−1
c = 14.9484 (3) Å	T = 150 K
β = 105.406 (1)°	Block, colourless
V = 2014.53 (6) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Nonius KappaCCD diffractometer	4569 independent reflections
Radiation source: fine-focus sealed tube	4469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
298 2.0 degree images with φ and ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→10
Tmin = 0.656, Tmax = 0.749	k = −22→22
16595 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)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.045	w = 1/[σ2(Fo2) + (0.0204P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4569 reflections	Δρmax = 0.41 e Å−3
227 parameters	Δρmin = −0.89 e Å−3
2 restraints	Absolute structure: Flack (1983), 2256 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.030 (12)

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
Sn	0.547277 (14)	0.045301 (7)	0.791813 (12)	0.01712 (5)
Cl1	0.25286 (7)	0.11982 (3)	0.75104 (4)	0.02502 (13)
Cl2	0.84601 (8)	−0.02426 (3)	0.84731 (4)	0.02268 (12)
C1	0.4134 (3)	−0.06314 (13)	0.77445 (16)	0.0196 (5)
C2	0.4971 (3)	−0.12794 (14)	0.75338 (18)	0.0251 (5)
H2	0.6146	−0.1243	0.7510	0.030*
C3	0.4122 (3)	−0.19752 (14)	0.73581 (18)	0.0293 (6)
H3	0.4699	−0.2405	0.7191	0.035*
C4	0.2430 (3)	−0.20458 (14)	0.74251 (19)	0.0278 (6)
H4	0.1850	−0.2524	0.7314	0.033*
C5	0.1592 (3)	−0.14099 (14)	0.76558 (18)	0.0269 (5)
H5	0.0438	−0.1454	0.7711	0.032*
C6	0.2438 (3)	−0.07124 (14)	0.78062 (17)	0.0229 (5)
H6	0.1845	−0.0280	0.7955	0.028*
C7	0.6122 (3)	0.08981 (12)	0.67105 (15)	0.0189 (4)
C8	0.4818 (3)	0.11348 (13)	0.59360 (16)	0.0229 (5)
H8	0.3639	0.1126	0.5957	0.028*
C9	0.5229 (3)	0.13846 (14)	0.51318 (17)	0.0269 (5)
H9	0.4331	0.1537	0.4607	0.032*
C10	0.6947 (3)	0.14098 (13)	0.51011 (17)	0.0262 (5)
H10	0.7225	0.1573	0.4552	0.031*
C11	0.8259 (3)	0.11967 (13)	0.58705 (18)	0.0259 (5)
H11	0.9440	0.1228	0.5856	0.031*
C12	0.7843 (3)	0.09383 (13)	0.66590 (16)	0.0222 (5)
H12	0.8750	0.0784	0.7179	0.027*
C13	0.6162 (3)	0.10926 (12)	0.91933 (16)	0.0209 (5)
C14	0.6982 (3)	0.07444 (14)	1.00306 (17)	0.0246 (5)
H14	0.7210	0.0211	1.0046	0.029*
C15	0.7473 (3)	0.11681 (15)	1.08452 (18)	0.0315 (6)
H15	0.8030	0.0922	1.1413	0.038*
C16	0.7159 (4)	0.19439 (15)	1.0836 (2)	0.0340 (6)
H16	0.7496	0.2231	1.1395	0.041*
C17	0.6349 (3)	0.23011 (15)	1.0009 (2)	0.0318 (6)
H17	0.6148	0.2836	0.9998	0.038*
C18	0.5825 (3)	0.18794 (13)	0.91879 (18)	0.0257 (5)
H18	0.5240	0.2126	0.8626	0.031*
N	0.1313 (3)	0.09715 (12)	0.93699 (16)	0.0265 (5)
H1A	0.172 (4)	0.0954 (16)	0.887 (2)	0.034 (8)*
H1B	0.043 (4)	0.0718 (19)	0.916 (2)	0.032 (8)*
C30	0.0840 (5)	0.17409 (17)	0.9603 (3)	0.0535 (9)
H30A	0.0163	0.1706	1.0061	0.080*
H30B	0.0144	0.1993	0.9042	0.080*
H30C	0.1897	0.2038	0.9863	0.080*
C20	0.2435 (5)	0.0556 (2)	1.0161 (3)	0.0560 (10)
H20A	0.3495	0.0852	1.0420	0.084*
H20B	0.2743	0.0058	0.9952	0.084*
H20C	0.1815	0.0482	1.0639	0.084*

	U11	U22	U33	U12	U13	U23
Sn	0.01594 (7)	0.01814 (7)	0.01734 (7)	−0.00084 (7)	0.00453 (5)	−0.00073 (8)
Cl1	0.0184 (3)	0.0280 (3)	0.0286 (3)	0.0049 (2)	0.0062 (2)	0.0038 (3)
Cl2	0.0170 (3)	0.0253 (3)	0.0250 (3)	0.0014 (2)	0.0043 (2)	0.0007 (3)
C1	0.0209 (11)	0.0241 (11)	0.0128 (11)	−0.0049 (10)	0.0027 (9)	−0.0002 (9)
C2	0.0238 (13)	0.0236 (12)	0.0317 (14)	−0.0029 (10)	0.0142 (11)	−0.0051 (10)
C3	0.0320 (13)	0.0230 (12)	0.0346 (15)	0.0016 (10)	0.0117 (12)	−0.0050 (11)
C4	0.0284 (13)	0.0219 (12)	0.0314 (14)	−0.0096 (11)	0.0052 (11)	−0.0040 (11)
C5	0.0205 (11)	0.0284 (12)	0.0314 (14)	−0.0053 (10)	0.0059 (10)	−0.0008 (11)
C6	0.0231 (12)	0.0239 (12)	0.0228 (13)	0.0021 (10)	0.0077 (10)	0.0005 (11)
C7	0.0223 (11)	0.0157 (10)	0.0180 (11)	−0.0031 (9)	0.0042 (9)	−0.0025 (9)
C8	0.0220 (12)	0.0231 (12)	0.0227 (13)	−0.0005 (9)	0.0043 (10)	−0.0002 (10)
C9	0.0339 (14)	0.0250 (12)	0.0200 (12)	0.0022 (10)	0.0036 (11)	−0.0004 (10)
C10	0.0422 (15)	0.0213 (12)	0.0185 (12)	0.0026 (10)	0.0136 (11)	0.0019 (10)
C11	0.0252 (13)	0.0252 (12)	0.0300 (14)	−0.0044 (10)	0.0122 (11)	−0.0017 (10)
C12	0.0230 (12)	0.0222 (11)	0.0202 (13)	−0.0020 (9)	0.0039 (10)	0.0003 (10)
C13	0.0193 (11)	0.0233 (11)	0.0207 (12)	−0.0027 (9)	0.0063 (10)	−0.0023 (10)
C14	0.0282 (13)	0.0231 (12)	0.0228 (13)	−0.0026 (10)	0.0075 (11)	−0.0014 (10)
C15	0.0358 (15)	0.0377 (15)	0.0213 (13)	−0.0058 (11)	0.0080 (12)	−0.0039 (11)
C16	0.0386 (15)	0.0391 (15)	0.0264 (15)	−0.0107 (12)	0.0127 (12)	−0.0134 (12)
C17	0.0346 (14)	0.0244 (12)	0.0406 (17)	−0.0057 (11)	0.0173 (13)	−0.0134 (12)
C18	0.0269 (13)	0.0223 (12)	0.0296 (14)	0.0001 (10)	0.0105 (11)	0.0002 (10)
N	0.0232 (11)	0.0300 (11)	0.0258 (12)	−0.0030 (9)	0.0058 (10)	−0.0033 (10)
C30	0.059 (2)	0.0319 (16)	0.081 (3)	0.0027 (14)	0.039 (2)	−0.0061 (16)
C20	0.045 (2)	0.078 (3)	0.041 (2)	0.0102 (16)	0.0024 (17)	0.0204 (17)

Sn—C7	2.152 (2)	C11—C12	1.383 (3)
Sn—C13	2.152 (2)	C11—H11	0.9500
Sn—C1	2.160 (2)	C12—H12	0.9500
Sn—Cl2	2.6098 (6)	C13—C14	1.390 (3)
Sn—Cl1	2.6153 (6)	C13—C18	1.403 (3)
C1—C6	1.389 (3)	C14—C15	1.390 (4)
C1—C2	1.395 (3)	C14—H14	0.9500
C2—C3	1.385 (3)	C15—C16	1.380 (4)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.387 (3)	C16—C17	1.384 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.389 (3)	C17—C18	1.397 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.385 (3)	C18—H18	0.9500
C5—H5	0.9500	N—C30	1.466 (4)
C6—H6	0.9500	N—C20	1.473 (4)
C7—C8	1.399 (3)	N—H1A	0.89 (3)
C7—C12	1.399 (3)	N—H1B	0.82 (3)
C8—C9	1.398 (3)	C30—H30A	0.9800
C8—H8	0.9500	C30—H30B	0.9800
C9—C10	1.386 (4)	C30—H30C	0.9800
C9—H9	0.9500	C20—H20A	0.9800
C10—C11	1.386 (4)	C20—H20B	0.9800
C10—H10	0.9500	C20—H20C	0.9800
C7—Sn—C13	119.52 (8)	C12—C11—H11	120.1
C7—Sn—C1	116.05 (8)	C10—C11—H11	120.1
C13—Sn—C1	124.43 (9)	C11—C12—C7	121.7 (2)
C7—Sn—Cl2	91.83 (6)	C11—C12—H12	119.2
C13—Sn—Cl2	87.94 (6)	C7—C12—H12	119.2
C1—Sn—Cl2	90.57 (7)	C14—C13—C18	118.7 (2)
C7—Sn—Cl1	91.49 (6)	C14—C13—Sn	121.19 (16)
C13—Sn—Cl1	87.10 (6)	C18—C13—Sn	120.14 (17)
C1—Sn—Cl1	91.40 (7)	C13—C14—C15	120.7 (2)
Cl2—Sn—Cl1	174.94 (2)	C13—C14—H14	119.6
C6—C1—C2	117.8 (2)	C15—C14—H14	119.6
C6—C1—Sn	122.82 (18)	C16—C15—C14	120.5 (3)
C2—C1—Sn	119.33 (16)	C16—C15—H15	119.7
C3—C2—C1	121.2 (2)	C14—C15—H15	119.7
C3—C2—H2	119.4	C15—C16—C17	119.6 (3)
C1—C2—H2	119.4	C15—C16—H16	120.2
C2—C3—C4	120.2 (2)	C17—C16—H16	120.2
C2—C3—H3	119.9	C16—C17—C18	120.4 (2)
C4—C3—H3	119.9	C16—C17—H17	119.8
C3—C4—C5	119.3 (2)	C18—C17—H17	119.8
C3—C4—H4	120.3	C17—C18—C13	120.1 (2)
C5—C4—H4	120.3	C17—C18—H18	120.0
C6—C5—C4	120.0 (2)	C13—C18—H18	120.0
C6—C5—H5	120.0	C30—N—C20	113.8 (3)
C4—C5—H5	120.0	C30—N—H1A	113.9 (18)
C5—C6—C1	121.4 (2)	C20—N—H1A	112.2 (19)
C5—C6—H6	119.3	C30—N—H1B	110 (2)
C1—C6—H6	119.3	C20—N—H1B	109 (2)
C8—C7—C12	117.8 (2)	H1A—N—H1B	97 (3)
C8—C7—Sn	120.62 (17)	N—C30—H30A	109.5
C12—C7—Sn	121.57 (17)	N—C30—H30B	109.5
C9—C8—C7	120.8 (2)	H30A—C30—H30B	109.5
C9—C8—H8	119.6	N—C30—H30C	109.5
C7—C8—H8	119.6	H30A—C30—H30C	109.5
C10—C9—C8	120.0 (2)	H30B—C30—H30C	109.5
C10—C9—H9	120.0	N—C20—H20A	109.5
C8—C9—H9	120.0	N—C20—H20B	109.5
C11—C10—C9	120.1 (2)	H20A—C20—H20B	109.5
C11—C10—H10	120.0	N—C20—H20C	109.5
C9—C10—H10	120.0	H20A—C20—H20C	109.5
C12—C11—C10	119.7 (2)	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N—H1A···Cl1	0.89 (3)	2.33 (3)	3.203 (2)	167 (3)
N—H1B···Cl2i	0.82 (3)	2.34 (3)	3.143 (2)	164 (3)
C2—H2···Cl2	0.95	2.67	3.309 (3)	125
C6—H6···Cl1	0.95	2.76	3.376 (2)	123
C8—H8···Cl1	0.95	2.70	3.344 (2)	126
C12—H12···Cl2	0.95	2.69	3.340 (2)	126

Table 1

Selected bond lengths (Å)

Sn—C7	2.152 (2)
Sn—C13	2.152 (2)
Sn—C1	2.160 (2)
Sn—Cl2	2.6098 (6)
Sn—Cl1	2.6153 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H1A⋯Cl1	0.89 (3)	2.33 (3)	3.203 (2)	167 (3)
N—H1B⋯Cl2i	0.82 (3)	2.34 (3)	3.143 (2)	164 (3)
C2—H2⋯Cl2	0.95	2.67	3.309 (3)	125
C6—H6⋯Cl1	0.95	2.76	3.376 (2)	123
C8—H8⋯Cl1	0.95	2.70	3.344 (2)	126
C12—H12⋯Cl2	0.95	2.69	3.340 (2)	126

Symmetry code: (i) .