Bis(cyclo-hexyl-ammonium) tetra-chlorido-(oxalato)stannate(IV).

The title salt, (C6H14N)2[Sn(C2O4)Cl4], was obtained as a by-product from the reaction between 2C6H14N(+)·C2O4 (2-)·1.5H2O and SnCl2·2H2O. The cyclo-hexyl-ammonium cation has a chair conformation. The complex anion consists of an oxalate anion chelating the SnCl4 moiety, resulting in a distorted octa-hedral coordination sphere of the Sn(IV) atom with the O atoms in equatorial cis positions. In the crystal, cations and anions are linked through N-H⋯O and N-H⋯Cl inter-actions into a layered arrangement parallel to (100).

Related literature

For applications of organotin(IV) compounds, see: Evans & Karpel (1985 ▶). For background to organotin(IV) chemistry, see: Ballmann et al. (2009 ▶); Meriem et al. (1989 ▶); Ng & Kumar Das (1997 ▶); Yin & Wang (2004 ▶); Zhang et al. (2006 ▶). For background to halogenidotin(IV) chemistry, see: Sarr & Diop (1990 ▶); Qamar-Kane & Diop (2010 ▶); Willey et al. (1998 ▶); Diallo et al. (2009 ▶). For related crystal structures with an oxalatotin(IV) moiety, see: Skapski et al. (1974 ▶); Gueye et al. (2012 ▶); Sow et al. (2010 ▶, 2013 ▶).

Experimental

Crystal data

(C6H14N)2[Sn(C2O4)Cl4]

M = 548.87

Monoclinic,

a = 11.2293 (9) Å

b = 15.715 (1) Å

c = 12.8464 (10) Å

β = 93.238 (2)°

V = 2263.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.62 mm−1

T = 115 K

0.17 × 0.08 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.770, T max = 0.953

9402 measured reflections

4979 independent reflections

4503 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.083

S = 1.12

4979 reflections

228 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.99 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019284/wm2756sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019284/wm2756Isup2.hkl

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

(C6H14N)2[Sn(C2O4)Cl4]	F(000) = 1104
Mr = 548.87	Dx = 1.611 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 41791 reflections
a = 11.2293 (9) Å	θ = 1.0–27.5°
b = 15.715 (1) Å	µ = 1.62 mm−1
c = 12.8464 (10) Å	T = 115 K
β = 93.238 (2)°	Prism, colourless
V = 2263.4 (3) Å3	0.17 × 0.08 × 0.03 mm
Z = 4

Nonius KappaCCD diffractometer	4979 independent reflections
Radiation source: fine-focus sealed tube	4503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ scans (κ = 0) + additional ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→10
Tmin = 0.770, Tmax = 0.953	k = −20→12
9402 measured reflections	l = −16→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0196P)2 + 5.6981P] where P = (Fo2 + 2Fc2)/3
4979 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 1.03 e Å−3
0 restraints	Δρmin = −0.99 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
Sn1	0.67656 (2)	0.922515 (13)	0.212827 (17)	0.02314 (7)
C1	0.5332 (3)	0.8427 (2)	0.3693 (2)	0.0240 (6)
C2	0.5332 (3)	0.77851 (19)	0.2768 (2)	0.0222 (6)
O1	0.5778 (2)	0.91628 (13)	0.35167 (16)	0.0231 (5)
O2	0.5826 (2)	0.80588 (14)	0.19492 (17)	0.0248 (5)
O3	0.4905 (2)	0.82201 (15)	0.45140 (17)	0.0326 (6)
O4	0.4875 (2)	0.70888 (14)	0.28564 (17)	0.0282 (5)
Cl1	0.74421 (8)	1.05949 (5)	0.26855 (7)	0.0349 (2)
Cl2	0.83254 (8)	0.84828 (6)	0.30516 (8)	0.0403 (2)
Cl3	0.75536 (10)	0.91018 (6)	0.04748 (8)	0.0428 (2)
Cl4	0.49591 (7)	0.98965 (5)	0.13685 (6)	0.02334 (16)
N1	0.5547 (2)	0.58436 (17)	0.1384 (2)	0.0254 (6)
H1A	0.5344	0.6179	0.1904	0.038*
H1B	0.5045	0.5406	0.1325	0.038*
H1C	0.5515	0.6138	0.0792	0.038*
C3	0.6796 (3)	0.5518 (2)	0.1610 (3)	0.0317 (7)
H3	0.6778	0.5129	0.2204	0.038*
C4	0.7205 (3)	0.5014 (2)	0.0690 (3)	0.0305 (7)
H4A	0.7208	0.5379	0.0081	0.037*
H4B	0.6654	0.4550	0.0536	0.037*
C5	0.8453 (4)	0.4659 (3)	0.0929 (3)	0.0397 (9)
H5A	0.8435	0.4252	0.1496	0.048*
H5B	0.8720	0.4365	0.0321	0.048*
C6	0.9310 (4)	0.5365 (3)	0.1229 (4)	0.0478 (11)
H6A	0.9388	0.5738	0.0636	0.057*
H6B	1.0088	0.5124	0.1415	0.057*
C7	0.8886 (4)	0.5888 (3)	0.2157 (3)	0.0439 (10)
H7A	0.8893	0.5532	0.2774	0.053*
H7B	0.9428	0.6360	0.2299	0.053*
C8	0.7630 (3)	0.6227 (3)	0.1914 (3)	0.0418 (9)
H8A	0.7352	0.6516	0.2522	0.050*
H8B	0.7641	0.6637	0.1349	0.050*
N2	0.3881 (3)	0.65674 (19)	0.4780 (2)	0.0357 (7)
H2A	0.3940	0.6415	0.4118	0.054*
H2B	0.4276	0.6197	0.5194	0.054*
H2C	0.4191	0.7084	0.4880	0.054*
C9	0.2600 (3)	0.6577 (2)	0.5030 (3)	0.0305 (7)
H9	0.2261	0.6012	0.4884	0.037*
C10	0.1935 (4)	0.7220 (3)	0.4339 (3)	0.0507 (12)
H10A	0.2013	0.7073	0.3613	0.061*
H10B	0.2274	0.7781	0.4459	0.061*
C11	0.0621 (5)	0.7226 (4)	0.4580 (4)	0.0613 (14)
H11A	0.0208	0.7657	0.4157	0.074*
H11B	0.0271	0.6679	0.4395	0.074*
C12	0.0451 (4)	0.7404 (3)	0.5710 (4)	0.0463 (10)
H12A	−0.0388	0.7354	0.5841	0.056*
H12B	0.0699	0.7983	0.5871	0.056*
C13	0.1164 (4)	0.6793 (3)	0.6413 (4)	0.0460 (10)
H13A	0.0836	0.6225	0.6326	0.055*
H13B	0.1095	0.6960	0.7134	0.055*
C14	0.2475 (3)	0.6780 (3)	0.6171 (3)	0.0357 (8)
H14A	0.2831	0.7330	0.6333	0.043*
H14B	0.2892	0.6355	0.6599	0.043*

	U11	U22	U33	U12	U13	U23
Sn1	0.02712 (12)	0.02014 (12)	0.02230 (12)	0.00106 (8)	0.00262 (8)	0.00254 (8)
C1	0.0337 (17)	0.0208 (15)	0.0172 (14)	0.0033 (13)	0.0001 (12)	0.0019 (11)
C2	0.0309 (17)	0.0183 (14)	0.0176 (14)	0.0010 (12)	0.0023 (12)	−0.0001 (11)
O1	0.0344 (12)	0.0175 (10)	0.0173 (10)	0.0006 (9)	0.0015 (9)	−0.0013 (8)
O2	0.0372 (13)	0.0199 (11)	0.0180 (10)	−0.0011 (9)	0.0073 (9)	−0.0024 (8)
O3	0.0566 (17)	0.0251 (12)	0.0170 (11)	−0.0004 (11)	0.0104 (11)	−0.0013 (9)
O4	0.0425 (14)	0.0202 (11)	0.0227 (11)	−0.0028 (10)	0.0078 (10)	−0.0031 (9)
Cl1	0.0358 (5)	0.0249 (4)	0.0430 (5)	−0.0060 (3)	−0.0077 (4)	0.0024 (3)
Cl2	0.0355 (5)	0.0359 (5)	0.0487 (5)	0.0104 (4)	−0.0055 (4)	0.0070 (4)
Cl3	0.0523 (6)	0.0416 (5)	0.0369 (5)	0.0105 (4)	0.0239 (4)	0.0083 (4)
Cl4	0.0294 (4)	0.0237 (4)	0.0168 (3)	0.0014 (3)	0.0000 (3)	0.0001 (3)
N1	0.0298 (15)	0.0261 (14)	0.0206 (13)	0.0021 (11)	0.0031 (11)	−0.0023 (10)
C3	0.0303 (18)	0.0380 (19)	0.0271 (17)	0.0054 (15)	0.0022 (14)	−0.0047 (14)
C4	0.0336 (18)	0.0315 (18)	0.0265 (17)	0.0019 (14)	0.0022 (14)	−0.0053 (14)
C5	0.037 (2)	0.039 (2)	0.043 (2)	0.0051 (17)	0.0044 (17)	−0.0049 (17)
C6	0.034 (2)	0.046 (2)	0.063 (3)	0.0009 (18)	0.004 (2)	−0.015 (2)
C7	0.034 (2)	0.049 (2)	0.047 (2)	−0.0044 (18)	−0.0078 (18)	−0.0111 (19)
C8	0.038 (2)	0.038 (2)	0.049 (2)	−0.0018 (17)	0.0006 (18)	−0.0200 (18)
N2	0.054 (2)	0.0232 (14)	0.0315 (15)	0.0092 (13)	0.0196 (14)	0.0088 (12)
C9	0.042 (2)	0.0235 (16)	0.0261 (16)	0.0048 (14)	0.0021 (15)	0.0010 (13)
C10	0.071 (3)	0.057 (3)	0.0249 (18)	0.030 (2)	0.0033 (19)	0.0093 (18)
C11	0.059 (3)	0.072 (3)	0.051 (3)	0.024 (3)	−0.022 (2)	0.000 (2)
C12	0.038 (2)	0.044 (2)	0.058 (3)	0.0096 (18)	0.0054 (19)	0.005 (2)
C13	0.042 (2)	0.049 (2)	0.048 (2)	0.0089 (19)	0.0129 (19)	0.012 (2)
C14	0.039 (2)	0.045 (2)	0.0228 (17)	0.0058 (17)	0.0025 (15)	0.0030 (15)

Sn1—O2	2.121 (2)	C7—C8	1.524 (6)
Sn1—O1	2.155 (2)	C7—H7A	0.9700
Sn1—Cl3	2.3547 (9)	C7—H7B	0.9700
Sn1—Cl2	2.3667 (9)	C8—H8A	0.9700
Sn1—Cl1	2.3794 (9)	C8—H8B	0.9700
Sn1—Cl4	2.4407 (8)	N2—C9	1.491 (5)
C1—O3	1.227 (4)	N2—H2A	0.8900
C1—O1	1.286 (4)	N2—H2B	0.8900
C1—C2	1.559 (4)	N2—H2C	0.8900
C2—O4	1.217 (4)	C9—C10	1.514 (5)
C2—O2	1.290 (4)	C9—C14	1.514 (5)
N1—C3	1.505 (4)	C9—H9	0.9800
N1—H1A	0.8900	C10—C11	1.524 (7)
N1—H1B	0.8900	C10—H10A	0.9700
N1—H1C	0.8900	C10—H10B	0.9700
C3—C8	1.493 (5)	C11—C12	1.501 (7)
C3—C4	1.515 (5)	C11—H11A	0.9700
C3—H3	0.9800	C11—H11B	0.9700
C4—C5	1.524 (5)	C12—C13	1.515 (6)
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C6	1.504 (6)	C13—C14	1.521 (5)
C5—H5A	0.9700	C13—H13A	0.9700
C5—H5B	0.9700	C13—H13B	0.9700
C6—C7	1.544 (6)	C14—H14A	0.9700
C6—H6A	0.9700	C14—H14B	0.9700
C6—H6B	0.9700
O2—Sn1—O1	76.97 (8)	C8—C7—H7A	109.6
O2—Sn1—Cl3	92.35 (6)	C6—C7—H7A	109.6
O1—Sn1—Cl3	168.53 (7)	C8—C7—H7B	109.6
O2—Sn1—Cl2	88.73 (7)	C6—C7—H7B	109.6
O1—Sn1—Cl2	87.92 (6)	H7A—C7—H7B	108.1
Cl3—Sn1—Cl2	96.10 (4)	C3—C8—C7	110.6 (3)
O2—Sn1—Cl1	164.34 (6)	C3—C8—H8A	109.5
O1—Sn1—Cl1	87.86 (6)	C7—C8—H8A	109.5
Cl3—Sn1—Cl1	102.47 (4)	C3—C8—H8B	109.5
Cl2—Sn1—Cl1	94.62 (3)	C7—C8—H8B	109.5
O2—Sn1—Cl4	86.17 (7)	H8A—C8—H8B	108.1
O1—Sn1—Cl4	84.01 (6)	C9—N2—H2A	109.5
Cl3—Sn1—Cl4	91.21 (3)	C9—N2—H2B	109.5
Cl2—Sn1—Cl4	171.25 (3)	H2A—N2—H2B	109.5
Cl1—Sn1—Cl4	88.47 (3)	C9—N2—H2C	109.5
O3—C1—O1	124.4 (3)	H2A—N2—H2C	109.5
O3—C1—C2	120.1 (3)	H2B—N2—H2C	109.5
O1—C1—C2	115.5 (3)	N2—C9—C10	109.3 (3)
O4—C2—O2	125.4 (3)	N2—C9—C14	110.7 (3)
O4—C2—C1	119.5 (3)	C10—C9—C14	110.9 (3)
O2—C2—C1	115.1 (3)	N2—C9—H9	108.6
C1—O1—Sn1	114.25 (19)	C10—C9—H9	108.6
C2—O2—Sn1	115.71 (19)	C14—C9—H9	108.6
C3—N1—H1A	109.5	C9—C10—C11	109.7 (4)
C3—N1—H1B	109.5	C9—C10—H10A	109.7
H1A—N1—H1B	109.5	C11—C10—H10A	109.7
C3—N1—H1C	109.5	C9—C10—H10B	109.7
H1A—N1—H1C	109.5	C11—C10—H10B	109.7
H1B—N1—H1C	109.5	H10A—C10—H10B	108.2
C8—C3—N1	111.1 (3)	C12—C11—C10	112.0 (4)
C8—C3—C4	112.4 (3)	C12—C11—H11A	109.2
N1—C3—C4	110.4 (3)	C10—C11—H11A	109.2
C8—C3—H3	107.6	C12—C11—H11B	109.2
N1—C3—H3	107.6	C10—C11—H11B	109.2
C4—C3—H3	107.6	H11A—C11—H11B	107.9
C3—C4—C5	110.5 (3)	C11—C12—C13	111.5 (4)
C3—C4—H4A	109.6	C11—C12—H12A	109.3
C5—C4—H4A	109.6	C13—C12—H12A	109.3
C3—C4—H4B	109.6	C11—C12—H12B	109.3
C5—C4—H4B	109.6	C13—C12—H12B	109.3
H4A—C4—H4B	108.1	H12A—C12—H12B	108.0
C6—C5—C4	110.4 (3)	C12—C13—C14	111.8 (3)
C6—C5—H5A	109.6	C12—C13—H13A	109.3
C4—C5—H5A	109.6	C14—C13—H13A	109.3
C6—C5—H5B	109.6	C12—C13—H13B	109.3
C4—C5—H5B	109.6	C14—C13—H13B	109.3
H5A—C5—H5B	108.1	H13A—C13—H13B	107.9
C5—C6—C7	111.7 (4)	C9—C14—C13	110.2 (3)
C5—C6—H6A	109.3	C9—C14—H14A	109.6
C7—C6—H6A	109.3	C13—C14—H14A	109.6
C5—C6—H6B	109.3	C9—C14—H14B	109.6
C7—C6—H6B	109.3	C13—C14—H14B	109.6
H6A—C6—H6B	107.9	H14A—C14—H14B	108.1
C8—C7—C6	110.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.89	1.97	2.853 (3)	169
N1—H1B···O1i	0.89	2.18	3.038 (4)	163
N1—H1C···O3ii	0.89	2.01	2.875 (4)	162
N2—H2A···O4	0.89	2.25	2.887 (4)	129
N2—H2A···Cl4i	0.89	2.78	3.315 (3)	120
N2—H2B···Cl4iii	0.89	2.38	3.262 (3)	169
N2—H2C···O3	0.89	2.02	2.869 (4)	158

Table 1

Selected bond lengths (Å)

Sn1—O2	2.121 (2)
Sn1—O1	2.155 (2)
Sn1—Cl3	2.3547 (9)
Sn1—Cl2	2.3667 (9)
Sn1—Cl1	2.3794 (9)
Sn1—Cl4	2.4407 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.89	1.97	2.853 (3)	169
N1—H1B⋯O1i	0.89	2.18	3.038 (4)	163
N1—H1C⋯O3ii	0.89	2.01	2.875 (4)	162
N2—H2A⋯O4	0.89	2.25	2.887 (4)	129
N2—H2A⋯Cl4i	0.89	2.78	3.315 (3)	120
N2—H2B⋯Cl4iii	0.89	2.38	3.262 (3)	169
N2—H2C⋯O3	0.89	2.02	2.869 (4)	158

Symmetry codes: (i) ; (ii) ; (iii) .