Tetra-methyl-ammonium aqua-trichlorido-oxalatostannate(IV) monohydrate.

The Sn(IV) atom in the title compound, [(CH(3))(4)N][Sn(C(2)O(4))Cl(3)(H(2)O)]·H(2)O, obtained from the reaction between SnCl(4) and [(CH(3))(4)N](2)C(2)O(4)·2H(2)O, is six-coordinated by three Cl atoms, an O atom of a water mol-ecule and two O atoms from an asymmetrically chelating oxalate anion. The environment around the Sn(IV) atom is distorted octa-hedral. The anions are connected by the lattice water mol-ecule through O-H⋯O hydrogen bonds, leading to a layered structure parallel to (010). The cations are located between these layers and besides Coulombic forces are connected to the anionic layers through weak C-H⋯O and C-H⋯Cl inter-actions.

Related literature

For background to halogentin(IV) chemistry, see: Hausen et al. (1986 ▶); Koutsantonis et al. (2003 ▶); Mahon et al. (2004 ▶); Patt-Siebel et al.(1986 ▶); Szymanska-Buzar et al. (2001 ▶); Tudela et al. (1986 ▶). For tin compounds containing an Sn—Cl bond in a cis- or trans-position, see: Fernandez et al. (2002 ▶); Hazell et al. (1998 ▶); Sow et al. (2010 ▶). For tin compounds containing carboxyl­ate moieties, see: Ng & Kumar Das (1993 ▶); Xu et al. (2003 ▶).

Experimental

Crystal data

(C4H12N)[Sn(C2O4)Cl3(H2O)]·H2O

M = 423.24

Monoclinic,

a = 7.2458 (1) Å

b = 22.2812 (2) Å

c = 9.6019 (1) Å

β = 98.015 (1)°

V = 1535.04 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.20 mm−1

T = 150 K

0.15 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.734, T max = 0.763

35849 measured reflections

4445 independent reflections

3855 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.062

S = 1.08

4445 reflections

175 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −0.79 e Å−3

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 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000895/wm2712sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000895/wm2712Isup2.hkl

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

(C4H12N)[Sn(C2O4)Cl3(H2O)]·H2O	F(000) = 832
Mr = 423.24	Dx = 1.831 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 29534 reflections
a = 7.2458 (1) Å	θ = 2.9–30.0°
b = 22.2812 (2) Å	µ = 2.20 mm−1
c = 9.6019 (1) Å	T = 150 K
β = 98.015 (1)°	Irregular, colourless
V = 1535.04 (3) Å3	0.15 × 0.15 × 0.13 mm
Z = 4

Nonius KappaCCD diffractometer	4445 independent reflections
Radiation source: fine-focus sealed tube	3855 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
461 1.3 degree images with ω scans	θmax = 30.0°, θmin = 4.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→10
Tmin = 0.734, Tmax = 0.763	k = −28→31
35849 measured reflections	l = −13→13

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0322P)2 + 0.5616P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
4445 reflections	Δρmax = 0.92 e Å−3
175 parameters	Δρmin = −0.79 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (5)

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	0.834510 (17)	0.112222 (6)	0.679281 (12)	0.02693 (6)
Cl1	0.61541 (8)	0.13476 (3)	0.83233 (5)	0.03867 (12)
Cl2	0.66559 (8)	0.14793 (3)	0.46760 (5)	0.04369 (14)
Cl3	1.01222 (8)	0.20243 (2)	0.72319 (6)	0.04152 (13)
O5	0.7216 (2)	0.02693 (7)	0.64413 (15)	0.0372 (3)
O1	1.00588 (18)	0.07154 (6)	0.84708 (13)	0.0278 (3)
O3	1.2565 (2)	0.01364 (6)	0.89271 (13)	0.0310 (3)
O4	1.28776 (19)	0.01308 (7)	0.61246 (13)	0.0323 (3)
O2	1.04412 (18)	0.07556 (6)	0.57415 (13)	0.0285 (3)
O6	0.5915 (2)	−0.03357 (7)	0.82856 (15)	0.0320 (3)
N	1.0670 (2)	0.16827 (7)	0.20003 (17)	0.0298 (3)
C1	1.1444 (2)	0.04194 (8)	0.81171 (17)	0.0241 (3)
C2	1.1635 (3)	0.04294 (8)	0.65224 (18)	0.0249 (3)
C3	0.9820 (3)	0.10701 (9)	0.1966 (3)	0.0370 (5)
H3A	0.8911	0.1053	0.2632	0.055*
H3B	1.0798	0.0771	0.2228	0.055*
H3C	0.9192	0.0985	0.1015	0.055*
C4	0.9184 (4)	0.21327 (11)	0.1570 (3)	0.0561 (7)
H4A	0.8558	0.2036	0.0624	0.084*
H4B	0.9739	0.2534	0.1566	0.084*
H4C	0.8274	0.2125	0.2235	0.084*
C5	1.1603 (4)	0.18245 (13)	0.3445 (2)	0.0500 (6)
H5A	1.2132	0.2230	0.3458	0.075*
H5B	1.2601	0.1533	0.3721	0.075*
H5C	1.0689	0.1804	0.4106	0.075*
C6	1.2081 (4)	0.17066 (11)	0.0997 (3)	0.0491 (6)
H6A	1.1482	0.1599	0.0051	0.074*
H6B	1.3090	0.1423	0.1300	0.074*
H6C	1.2592	0.2113	0.0984	0.074*
H50B	0.703 (4)	0.0121 (13)	0.562 (2)	0.058 (8)*
H60B	0.481 (3)	−0.0227 (14)	0.829 (3)	0.057 (9)*
H60A	0.647 (4)	−0.0270 (13)	0.909 (2)	0.053 (8)*
H50A	0.668 (4)	0.0068 (12)	0.704 (3)	0.059 (9)*

	U11	U22	U33	U12	U13	U23
Sn	0.02791 (9)	0.02922 (8)	0.02369 (8)	0.00383 (4)	0.00368 (5)	0.00042 (4)
Cl1	0.0382 (3)	0.0436 (3)	0.0363 (3)	0.0062 (2)	0.0124 (2)	−0.0069 (2)
Cl2	0.0376 (3)	0.0596 (3)	0.0325 (3)	0.0146 (2)	0.0002 (2)	0.0094 (2)
Cl3	0.0423 (3)	0.0295 (2)	0.0520 (3)	−0.0019 (2)	0.0039 (2)	0.0029 (2)
O5	0.0468 (9)	0.0414 (8)	0.0256 (7)	−0.0136 (7)	0.0122 (6)	−0.0087 (6)
O1	0.0321 (7)	0.0308 (6)	0.0208 (6)	0.0045 (5)	0.0048 (5)	−0.0001 (5)
O3	0.0316 (7)	0.0376 (7)	0.0230 (6)	0.0047 (6)	0.0014 (5)	0.0034 (5)
O4	0.0291 (7)	0.0442 (8)	0.0230 (6)	0.0069 (6)	0.0018 (5)	−0.0051 (5)
O2	0.0287 (7)	0.0362 (7)	0.0209 (6)	0.0051 (5)	0.0040 (5)	0.0033 (5)
O6	0.0323 (8)	0.0396 (8)	0.0239 (7)	0.0062 (6)	0.0031 (6)	0.0003 (5)
N	0.0361 (9)	0.0254 (7)	0.0272 (8)	−0.0021 (6)	0.0018 (6)	−0.0007 (6)
C1	0.0268 (9)	0.0247 (8)	0.0205 (8)	−0.0031 (6)	0.0024 (7)	−0.0013 (6)
C2	0.0260 (9)	0.0281 (8)	0.0199 (8)	−0.0025 (7)	0.0014 (6)	−0.0014 (6)
C3	0.0409 (12)	0.0269 (9)	0.0445 (12)	−0.0048 (8)	0.0106 (10)	−0.0014 (8)
C4	0.0539 (15)	0.0325 (12)	0.0774 (19)	0.0084 (10)	−0.0061 (13)	0.0040 (11)
C5	0.0551 (15)	0.0598 (15)	0.0319 (11)	−0.0207 (12)	−0.0052 (10)	0.0029 (10)
C6	0.0646 (16)	0.0399 (12)	0.0477 (13)	−0.0152 (11)	0.0249 (12)	−0.0067 (10)

Sn—O5	2.0781 (15)	N—C3	1.496 (2)
Sn—O1	2.0980 (13)	N—C6	1.500 (3)
Sn—O2	2.1025 (13)	C1—C2	1.557 (2)
Sn—Cl2	2.3598 (5)	C3—H3A	0.9800
Sn—Cl1	2.3627 (5)	C3—H3B	0.9800
Sn—Cl3	2.3926 (5)	C3—H3C	0.9800
O5—H50B	0.850 (17)	C4—H4A	0.9800
O5—H50A	0.859 (17)	C4—H4B	0.9800
O1—C1	1.285 (2)	C4—H4C	0.9800
O3—C1	1.219 (2)	C5—H5A	0.9800
O4—C2	1.223 (2)	C5—H5B	0.9800
O2—C2	1.288 (2)	C5—H5C	0.9800
O6—H60B	0.836 (17)	C6—H6A	0.9800
O6—H60A	0.836 (17)	C6—H6B	0.9800
N—C4	1.488 (3)	C6—H6C	0.9800
N—C5	1.490 (3)
O5—Sn—O1	84.67 (6)	O1—C1—C2	115.63 (15)
O5—Sn—O2	82.02 (6)	O4—C2—O2	126.11 (16)
O1—Sn—O2	79.11 (5)	O4—C2—C1	118.03 (16)
O5—Sn—Cl2	91.33 (5)	O2—C2—C1	115.85 (15)
O1—Sn—Cl2	170.93 (4)	N—C3—H3A	109.5
O2—Sn—Cl2	92.30 (4)	N—C3—H3B	109.5
O5—Sn—Cl1	90.68 (4)	H3A—C3—H3B	109.5
O1—Sn—Cl1	89.50 (4)	N—C3—H3C	109.5
O2—Sn—Cl1	166.95 (4)	H3A—C3—H3C	109.5
Cl2—Sn—Cl1	98.70 (2)	H3B—C3—H3C	109.5
O5—Sn—Cl3	170.75 (5)	N—C4—H4A	109.5
O1—Sn—Cl3	88.93 (4)	N—C4—H4B	109.5
O2—Sn—Cl3	90.23 (4)	H4A—C4—H4B	109.5
Cl2—Sn—Cl3	94.03 (2)	N—C4—H4C	109.5
Cl1—Sn—Cl3	95.95 (2)	H4A—C4—H4C	109.5
Sn—O5—H50B	121 (2)	H4B—C4—H4C	109.5
Sn—O5—H50A	125 (2)	N—C5—H5A	109.5
H50B—O5—H50A	113 (3)	N—C5—H5B	109.5
C1—O1—Sn	114.77 (11)	H5A—C5—H5B	109.5
C2—O2—Sn	114.29 (11)	N—C5—H5C	109.5
H60B—O6—H60A	107 (3)	H5A—C5—H5C	109.5
C4—N—C5	109.4 (2)	H5B—C5—H5C	109.5
C4—N—C3	109.18 (18)	N—C6—H6A	109.5
C5—N—C3	110.24 (17)	N—C6—H6B	109.5
C4—N—C6	109.2 (2)	H6A—C6—H6B	109.5
C5—N—C6	109.25 (18)	N—C6—H6C	109.5
C3—N—C6	109.49 (16)	H6A—C6—H6C	109.5
O3—C1—O1	124.90 (16)	H6B—C6—H6C	109.5
O3—C1—C2	119.47 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H50A···O6	0.86 (2)	1.66 (2)	2.511 (2)	173 (3)
O5—H50B···O4i	0.85 (2)	1.78 (2)	2.6120 (19)	168 (3)
O6—H60B···O3ii	0.84 (2)	1.99 (2)	2.792 (2)	160 (3)
O6—H60A···O3iii	0.84 (2)	1.95 (2)	2.7840 (19)	172 (3)
O6—H60B···O4ii	0.84 (2)	2.47 (3)	2.993 (2)	122 (3)
C6—H6B···O6i	0.98	2.54	3.411 (3)	148
C6—H6A···Cl3iv	0.98	2.91	3.762 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H50A⋯O6	0.86 (2)	1.66 (2)	2.511 (2)	173 (3)
O5—H50B⋯O4i	0.85 (2)	1.78 (2)	2.6120 (19)	168 (3)
O6—H60B⋯O3ii	0.84 (2)	1.99 (2)	2.792 (2)	160 (3)
O6—H60A⋯O3iii	0.84 (2)	1.95 (2)	2.7840 (19)	172 (3)
O6—H60B⋯O4ii	0.84 (2)	2.47 (3)	2.993 (2)	122 (3)
C6—H6B⋯O6i	0.98	2.54	3.411 (3)	148
C6—H6A⋯Cl3iv	0.98	2.91	3.762 (3)	146

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