Bis(dicyclo­hexyl­ammonium) μ-oxalato-κ4O1,O2:O1′,O2′-bis­[aqua­(oxalato-κ2O1,O2)diphenyl­stannate(IV)]

Gueye, N.; Diop, L.; Molloy, K.C.K.; Kociok-Köhn, G.

doi:10.1107/S1600536810046738

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1645-m1646

https://doi.org/10.1107/S1600536810046738

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Bis(dicyclohexylammonium) μ-oxalato-κ⁴O¹,O²:O^1′,O^2′-bis[aqua(oxalato-κ²O¹,O²)diphenylstannate(IV)]

Ndongo Gueye,^a Libasse Diop,^a ^* K. C. Kieran Molloy ^b and Gabrielle Kociok-Köhn ^b

^aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDepartment of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, England
^*Correspondence e-mail: dlibasse@gmail.com

(Received 2 September 2010; accepted 11 November 2010; online 24 November 2010)

The structure of the title compound, (C₁₂H₂₄N)₂[Sn₂(C₆H₅)₄(C₂O₄)₃(H₂O)₂], consists of a bischelating oxalate ion, located on an inversion center, which is linked to two SnPh₂ groups. The coordination sphere of the Sn(IV) ion is completed by a monochelating oxalate anion and a water molecule. The Sn(IV) atoms are thus seven-coordinated. The discrete binuclear units are further connected by hydrogen bonds, leading to a supramolecular crystal structure. The asymmetric unit contains one half dianion and one (Cy₂NH₂)⁺ cation.

Related literature

For background to organotin(IV) chemistry, see: Ballmann et al. (2009 ); Diallo et al. (2007 ); Diassé-Sarr et al. (1997 ); Ng et al. (1992 ); Singh et al. (2008 ); de Sousa et al. (2007 ); Wang et al. (2009 ); Xanthopoulou et al. (2007 , 2008 ); Zia-ur-Rahman et al. (2007 ). For related Sn(IV) structures, see: Diop et al. (2002 , 2003 ).

Experimental

Crystal data

(C₁₂H₂₄N)₂[Sn₂(C₆H₅)₄(C₂O₄)₃(H₂O)₂]
M_r = 1210.52
Monoclinic, P 2₁ /n
a = 13.1725 (4) Å
b = 14.6121 (4) Å
c = 14.1139 (4) Å
β = 100.869 (2)°
V = 2667.88 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 150 K
0.2 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.825, T_max = 0.825
48411 measured reflections
6114 independent reflections
4069 reflections with I > 2σ(I)
R_int = 0.126

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.082
S = 1.01
6114 reflections
341 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O4ⁱ	0.90 (4)	1.77 (4)	2.663 (3)	175 (4)
N—H1A⋯O3ⁱⁱ	0.84 (4)	2.12 (3)	2.910 (4)	155 (3)
N—H1A⋯O4ⁱⁱ	0.84 (4)	2.37 (4)	2.986 (4)	130 (3)
N—H1B⋯O6ⁱⁱⁱ	0.91 (4)	2.08 (4)	2.960 (4)	164 (4)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) 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, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046738/bh2310sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046738/bh2310Isup2.hkl

checkCIF report

Comment top

In the dynamic of our research work on organotin(IV) chemistry (Diallo et al., 2007; Diassé-Sarr et al., 1997) because of several applications found (Xanthopoulou et al., 2007, 2008; Zia-ur-Rahman et al., 2007; Singh et al., 2008; Wang et al., 2009; Ballmann et al., 2009; de Sousa et al., 2007) and our interest in the coordinating behaviour of oxyanions in this family of compounds, we had yet reported the crystal structures of C₂O₄(SnPh₃)₂ (Diop et al., 2003) and SO₄(SnPh₃)₂.H₂O (Diop et al., 2002) and have initiated here the study of the interactions between (Cy₂NH₂)₂C₂O₄.2H₂O and C₂O₄(SnPh₃)₂ which has yielded the studied compound.

The asymmetric unit consists of one half of the molecule, located about an inversion centre at the mid-point of the C3—C3ⁱ bond (symmetry code i: -x, 1 - y, -z). In its units structure two SnPh₂ residues are linked by a central bichelating oxalate ion [O₅O₆:O₅O₆] and every SnPh₂ residue is then linked to another monochelating anion [O1, O2]. A water molecule completes the tin centre coordination to seven, which can be described as a distorted trans-C₂SnO₅ pentagonal bipyramidal geometry [C—Sn—C angle: 168.75 (13)°]. Within the bridging carboxylate all the C—O bonds are equal within experimental error, implying complete delocalization of double-bond character within this residue. The bond lengths C1—O1 and C2—O2, [1.273 (4) Å], and C2—O3, C1—O4 [1.225 (4) and 1.247 (4) Å] indicate respectively a single and double bond character; the bond length C1—O4 results from involvement of O4 in two distinct hydrogen bonds. Among the Sn—O bonds, Sn1—O6 is notably longer, O6 being the only oxygen of this kind involved in hydrogen bonding.

Every moiety is then connected to its neighbour by three types of hydrogen bonds: one O—H···O type involving an H atom of the water molecule and one O atom of monochelating oxalate [O7—H7B···O4], one N—H···O contact involving one O atom of the bichelating oxalate anion and the cation [N—H1B···O6] and a third bifurcated one also involving the cation [N—H1A···O3 and N—H1A···O4], giving a supramolecular crystal structure.

A similar structure, bearing butyl groups in place of phenyl, was previously reported (Ng et al., 1992).

Related literature top

For background to organotin(IV) chemistry, see: Ballmann et al. (2009); Diallo et al. (2007); Diassé-Sarr et al. (1997); Ng et al. (1992); Singh et al. (2008); de Sousa et al. (2007); Wang et al. (2009); Xanthopoulou et al. (2007, 2008); Zia-ur-Rahman et al. (2007). For related Sn(IV) structures, see: Diop et al. (2002, 2003).

Experimental top

Crystals of the title compound were obtained by allowing (Cy₂NH₂)₂C₂O₄.2H₂O (90 mmol in 15 ml e thanol) to react with C₂O₄(SnPh₃)₂ (45 mmol in 15 ml e thanol). The mixture was stirred during several hours and slow solvent evaporation afforded crystals suitable for X-rays studies.

Structure description top

A similar structure, bearing butyl groups in place of phenyl, was previously reported (Ng et al., 1992).

For background to organotin(IV) chemistry, see: Ballmann et al. (2009); Diallo et al. (2007); Diassé-Sarr et al. (1997); Ng et al. (1992); Singh et al. (2008); de Sousa et al. (2007); Wang et al. (2009); Xanthopoulou et al. (2007, 2008); Zia-ur-Rahman et al. (2007). For related Sn(IV) structures, see: Diop et al. (2002, 2003).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A part of the crystal structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed bonds represent hydrogen bonds.

Bis(dicyclohexylammonium) µ-oxalato-κ⁴O¹,O²:O^1',O^2'- bis[aqua(oxalato-κ²O¹,O²)diphenylstannate(IV)] top

Crystal data top

(C₁₂H₂₄N)₂[Sn₂(C₆H₅)₄(C₂O₄)₃(H₂O)₂]	F(000) = 1244
M_r = 1210.52	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 29450 reflections
a = 13.1725 (4) Å	θ = 2.9–27.5°
b = 14.6121 (4) Å	µ = 1.00 mm⁻¹
c = 14.1139 (4) Å	T = 150 K
β = 100.869 (2)°	Irregular, colourless
V = 2667.88 (13) Å³	0.2 × 0.2 × 0.2 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	6114 independent reflections
Radiation source: fine-focus sealed tube	4069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.126
293 2.0 degree images with φ and ω scans	θ_max = 27.5°, θ_min = 4.1°
Absorption correction: multi-scan (SORTAV;Blessing, 1995)	h = −17→17
T_min = 0.825, T_max = 0.825	k = −18→18
48411 measured reflections	l = −18→18

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0335P)² + 0.6086P] where P = (F_o² + 2F_c²)/3
6114 reflections	(Δ/σ)_max = 0.001
341 parameters	Δρ_max = 0.54 e Å⁻³
2 restraints	Δρ_min = −0.72 e Å⁻³
0 constraints

Crystal data top

(C₁₂H₂₄N)₂[Sn₂(C₆H₅)₄(C₂O₄)₃(H₂O)₂]	V = 2667.88 (13) Å³
M_r = 1210.52	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1725 (4) Å	µ = 1.00 mm⁻¹
b = 14.6121 (4) Å	T = 150 K
c = 14.1139 (4) Å	0.2 × 0.2 × 0.2 mm
β = 100.869 (2)°

Data collection top

Nonius KappaCCD diffractometer	6114 independent reflections
Absorption correction: multi-scan (SORTAV;Blessing, 1995)	4069 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.825	R_int = 0.126
48411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.54 e Å⁻³
6114 reflections	Δρ_min = −0.72 e Å⁻³
341 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn	0.208644 (18)	0.515508 (15)	0.133115 (17)	0.02034 (8)
O1	0.27245 (18)	0.37817 (14)	0.16466 (16)	0.0235 (5)
O2	0.35282 (17)	0.53257 (14)	0.24319 (16)	0.0242 (5)
O3	0.47106 (18)	0.45574 (15)	0.34724 (17)	0.0285 (6)
O4	0.38762 (18)	0.29623 (15)	0.26721 (17)	0.0275 (6)
O5	0.09563 (17)	0.41884 (14)	0.04184 (16)	0.0230 (5)
O6	0.06436 (17)	0.60103 (14)	0.04207 (15)	0.0210 (5)
O7	0.2413 (2)	0.67274 (16)	0.18266 (19)	0.0292 (6)
H7A	0.292 (2)	0.669 (3)	0.233 (2)	0.052 (14)*
H7B	0.197 (3)	0.712 (3)	0.202 (3)	0.074 (16)*
N	−0.0015 (2)	0.2042 (2)	−0.0277 (2)	0.0214 (6)
H1A	−0.019 (3)	0.170 (2)	−0.076 (3)	0.027 (10)*
H1B	−0.027 (3)	0.261 (3)	−0.044 (3)	0.038 (11)*
C1	0.3500 (3)	0.3702 (2)	0.2332 (2)	0.0216 (8)
C2	0.3979 (3)	0.4602 (2)	0.2795 (2)	0.0211 (7)
C3	0.0088 (3)	0.4480 (2)	−0.0001 (2)	0.0196 (7)
C4	0.1110 (3)	0.5052 (2)	0.2372 (2)	0.0225 (7)
C5	0.0459 (3)	0.5767 (2)	0.2523 (3)	0.0277 (8)
H5	0.0467	0.6321	0.2172	0.033*
C6	−0.0202 (3)	0.5686 (3)	0.3177 (3)	0.0331 (9)
H6	−0.0632	0.6185	0.3277	0.040*
C7	−0.0237 (3)	0.4886 (3)	0.3681 (3)	0.0356 (9)
H7	−0.0690	0.4828	0.4127	0.043*
C8	0.0399 (3)	0.4162 (3)	0.3531 (3)	0.0359 (9)
H8	0.0380	0.3607	0.3880	0.043*
C9	0.1059 (3)	0.4239 (2)	0.2882 (3)	0.0295 (8)
H9	0.1482	0.3735	0.2781	0.035*
C10	0.2855 (3)	0.5464 (2)	0.0178 (3)	0.0276 (8)
C11	0.3816 (3)	0.5881 (3)	0.0352 (3)	0.0453 (11)
H11	0.4136	0.6027	0.0995	0.054*
C12	0.4320 (4)	0.6091 (4)	−0.0408 (4)	0.0664 (15)
H12	0.4979	0.6378	−0.0276	0.080*
C13	0.3872 (4)	0.5888 (3)	−0.1337 (3)	0.0533 (13)
H13	0.4220	0.6032	−0.1850	0.064*
C14	0.2922 (4)	0.5477 (3)	−0.1528 (3)	0.0485 (11)
H14	0.2609	0.5336	−0.2174	0.058*
C15	0.2416 (3)	0.5266 (3)	−0.0778 (3)	0.0377 (9)
H15	0.1756	0.4981	−0.0919	0.045*
C16	0.1143 (2)	0.2108 (2)	−0.0052 (2)	0.0218 (7)
H16	0.1344	0.2502	0.0533	0.026*
C17	0.1521 (3)	0.2565 (2)	−0.0890 (2)	0.0256 (8)
H17A	0.1338	0.2183	−0.1476	0.031*
H17B	0.1180	0.3168	−0.1024	0.031*
C18	0.2684 (3)	0.2693 (2)	−0.0643 (3)	0.0308 (9)
H18A	0.2863	0.3099	−0.0075	0.037*
H18B	0.2927	0.2986	−0.1192	0.037*
C19	0.3215 (3)	0.1774 (3)	−0.0425 (3)	0.0355 (9)
H19A	0.3969	0.1869	−0.0231	0.043*
H19B	0.3092	0.1392	−0.1015	0.043*
C20	0.2811 (3)	0.1276 (3)	0.0380 (3)	0.0327 (9)
H20A	0.3134	0.0663	0.0471	0.039*
H20B	0.3018	0.1621	0.0990	0.039*
C21	0.1647 (3)	0.1171 (2)	0.0165 (3)	0.0270 (8)
H21A	0.1413	0.0894	0.0727	0.032*
H21B	0.1439	0.0761	−0.0396	0.032*
C22	−0.0561 (3)	0.1646 (2)	0.0476 (2)	0.0234 (8)
H22	−0.0323	0.1001	0.0613	0.028*
C23	−0.1710 (3)	0.1642 (3)	0.0064 (3)	0.0332 (9)
H23A	−0.1847	0.1254	−0.0521	0.040*
H23B	−0.1942	0.2272	−0.0123	0.040*
C24	−0.2322 (3)	0.1273 (3)	0.0812 (3)	0.0368 (10)
H24A	−0.3071	0.1303	0.0542	0.044*
H24B	−0.2137	0.0623	0.0953	0.044*
C25	−0.2087 (3)	0.1823 (3)	0.1736 (3)	0.0371 (9)
H25A	−0.2462	0.1557	0.2216	0.045*
H25B	−0.2330	0.2461	0.1607	0.045*
C26	−0.0935 (3)	0.1823 (3)	0.2141 (3)	0.0402 (10)
H26A	−0.0706	0.1190	0.2321	0.048*
H26B	−0.0795	0.2203	0.2732	0.048*
C27	−0.0316 (3)	0.2196 (3)	0.1407 (2)	0.0324 (9)
H27A	−0.0494	0.2848	0.1271	0.039*
H27B	0.0433	0.2158	0.1678	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01965 (13)	0.01890 (12)	0.02124 (13)	0.00066 (11)	0.00070 (8)	0.00046 (11)
O1	0.0233 (14)	0.0203 (12)	0.0240 (13)	0.0026 (10)	−0.0033 (11)	−0.0020 (10)
O2	0.0238 (13)	0.0161 (13)	0.0292 (13)	0.0016 (9)	−0.0043 (10)	0.0021 (10)
O3	0.0284 (14)	0.0251 (13)	0.0266 (14)	−0.0012 (10)	−0.0089 (11)	0.0018 (10)
O4	0.0286 (14)	0.0193 (13)	0.0314 (14)	0.0034 (10)	−0.0025 (11)	0.0037 (10)
O5	0.0225 (13)	0.0177 (12)	0.0262 (13)	0.0014 (10)	−0.0020 (11)	−0.0027 (10)
O6	0.0217 (13)	0.0192 (12)	0.0201 (12)	0.0006 (10)	−0.0009 (10)	−0.0002 (10)
O7	0.0260 (16)	0.0237 (14)	0.0353 (16)	0.0013 (11)	−0.0007 (13)	−0.0018 (12)
N	0.0246 (17)	0.0186 (17)	0.0208 (17)	−0.0001 (12)	0.0042 (14)	−0.0004 (14)
C1	0.021 (2)	0.0227 (19)	0.0225 (19)	0.0008 (14)	0.0082 (16)	−0.0007 (15)
C2	0.0206 (19)	0.0233 (19)	0.0203 (18)	−0.0011 (14)	0.0060 (15)	−0.0010 (14)
C3	0.023 (2)	0.0193 (17)	0.0166 (16)	0.0008 (14)	0.0031 (14)	−0.0021 (13)
C4	0.0218 (17)	0.027 (2)	0.0175 (17)	−0.0008 (14)	−0.0009 (13)	−0.0022 (14)
C5	0.024 (2)	0.029 (2)	0.028 (2)	0.0001 (15)	−0.0010 (16)	0.0000 (15)
C6	0.021 (2)	0.045 (2)	0.033 (2)	−0.0008 (17)	0.0036 (17)	−0.0033 (18)
C7	0.029 (2)	0.048 (2)	0.032 (2)	−0.0127 (18)	0.0105 (17)	−0.0046 (19)
C8	0.036 (2)	0.038 (2)	0.034 (2)	−0.0119 (18)	0.0066 (19)	0.0024 (18)
C9	0.031 (2)	0.027 (2)	0.031 (2)	−0.0032 (16)	0.0058 (17)	−0.0017 (16)
C10	0.029 (2)	0.0265 (19)	0.029 (2)	0.0055 (15)	0.0077 (16)	0.0054 (15)
C11	0.030 (2)	0.070 (3)	0.036 (2)	−0.007 (2)	0.0053 (19)	0.008 (2)
C12	0.033 (3)	0.105 (4)	0.065 (4)	−0.011 (3)	0.017 (3)	0.019 (3)
C13	0.050 (3)	0.072 (3)	0.045 (3)	0.015 (2)	0.028 (2)	0.016 (2)
C14	0.069 (3)	0.048 (3)	0.031 (2)	0.004 (2)	0.015 (2)	0.0013 (19)
C15	0.048 (3)	0.035 (2)	0.033 (2)	−0.0038 (18)	0.0124 (19)	−0.0001 (18)
C16	0.0198 (19)	0.0236 (18)	0.0212 (18)	0.0027 (14)	0.0020 (15)	0.0001 (14)
C17	0.029 (2)	0.0263 (19)	0.0211 (19)	0.0022 (15)	0.0042 (16)	0.0009 (15)
C18	0.026 (2)	0.040 (2)	0.028 (2)	0.0013 (16)	0.0100 (17)	0.0019 (17)
C19	0.024 (2)	0.045 (2)	0.036 (2)	0.0081 (17)	0.0031 (17)	−0.0076 (18)
C20	0.027 (2)	0.035 (2)	0.034 (2)	0.0090 (16)	−0.0025 (17)	−0.0011 (17)
C21	0.028 (2)	0.0224 (19)	0.029 (2)	0.0033 (15)	0.0002 (16)	−0.0016 (15)
C22	0.027 (2)	0.0194 (18)	0.0237 (19)	0.0025 (14)	0.0054 (16)	0.0037 (14)
C23	0.030 (2)	0.042 (2)	0.028 (2)	−0.0047 (17)	0.0056 (17)	−0.0043 (17)
C24	0.026 (2)	0.049 (2)	0.037 (2)	−0.0064 (18)	0.0085 (18)	−0.0029 (19)
C25	0.032 (2)	0.047 (2)	0.035 (2)	−0.0018 (18)	0.0132 (18)	−0.0056 (19)
C26	0.038 (3)	0.058 (3)	0.026 (2)	−0.010 (2)	0.0104 (18)	−0.0021 (19)
C27	0.030 (2)	0.043 (2)	0.023 (2)	−0.0064 (17)	0.0038 (17)	−0.0043 (17)

Geometric parameters (Å, º) top

Sn—C10	2.121 (3)	C13—C14	1.368 (6)
Sn—C4	2.132 (3)	C13—H13	0.9500
Sn—O1	2.189 (2)	C14—C15	1.388 (5)
Sn—O2	2.229 (2)	C14—H14	0.9500
Sn—O5	2.269 (2)	C15—H15	0.9500
Sn—O7	2.416 (2)	C16—C17	1.522 (4)
Sn—O6	2.430 (2)	C16—C21	1.527 (4)
O1—C1	1.273 (4)	C16—H16	1.0000
O2—C2	1.273 (4)	C17—C18	1.517 (5)
O3—C2	1.225 (4)	C17—H17A	0.9900
O4—C1	1.247 (4)	C17—H17B	0.9900
O5—C3	1.259 (4)	C18—C19	1.518 (5)
O6—C3ⁱ	1.256 (4)	C18—H18A	0.9900
O7—H7A	0.886 (19)	C18—H18B	0.9900
O7—H7B	0.896 (19)	C19—C20	1.527 (5)
N—C16	1.500 (4)	C19—H19A	0.9900
N—C22	1.507 (4)	C19—H19B	0.9900
N—H1A	0.85 (4)	C20—C21	1.514 (5)
N—H1B	0.91 (4)	C20—H20A	0.9900
C1—C2	1.548 (5)	C20—H20B	0.9900
C3—O6ⁱ	1.256 (4)	C21—H21A	0.9900
C3—C3ⁱ	1.537 (7)	C21—H21B	0.9900
C4—C5	1.394 (5)	C22—C23	1.516 (5)
C4—C9	1.397 (5)	C22—C27	1.522 (5)
C5—C6	1.389 (5)	C22—H22	1.0000
C5—H5	0.9500	C23—C24	1.540 (5)
C6—C7	1.373 (5)	C23—H23A	0.9900
C6—H6	0.9500	C23—H23B	0.9900
C7—C8	1.390 (5)	C24—C25	1.514 (5)
C7—H7	0.9500	C24—H24A	0.9900
C8—C9	1.382 (5)	C24—H24B	0.9900
C8—H8	0.9500	C25—C26	1.518 (5)
C9—H9	0.9500	C25—H25A	0.9900
C10—C11	1.385 (5)	C25—H25B	0.9900
C10—C15	1.394 (5)	C26—C27	1.534 (5)
C11—C12	1.398 (6)	C26—H26A	0.9900
C11—H11	0.9500	C26—H26B	0.9900
C12—C13	1.366 (7)	C27—H27A	0.9900
C12—H12	0.9500	C27—H27B	0.9900

C10—Sn—C4	168.75 (13)	C14—C15—C10	121.4 (4)
C10—Sn—O1	97.50 (11)	C14—C15—H15	119.3
C4—Sn—O1	93.06 (10)	C10—C15—H15	119.3
C10—Sn—O2	92.53 (12)	N—C16—C17	109.4 (3)
C4—Sn—O2	94.18 (11)	N—C16—C21	111.8 (3)
O1—Sn—O2	73.55 (8)	C17—C16—C21	110.9 (3)
C10—Sn—O5	93.06 (12)	N—C16—H16	108.2
C4—Sn—O5	86.04 (10)	C17—C16—H16	108.2
O1—Sn—O5	74.35 (8)	C21—C16—H16	108.2
O2—Sn—O5	147.87 (8)	C18—C17—C16	109.9 (3)
C10—Sn—O7	86.30 (11)	C18—C17—H17A	109.7
C4—Sn—O7	88.01 (10)	C16—C17—H17A	109.7
O1—Sn—O7	140.57 (9)	C18—C17—H17B	109.7
O2—Sn—O7	67.06 (8)	C16—C17—H17B	109.7
O5—Sn—O7	144.90 (8)	H17A—C17—H17B	108.2
C10—Sn—O6	85.62 (11)	C17—C18—C19	110.2 (3)
C4—Sn—O6	83.54 (10)	C17—C18—H18A	109.6
O1—Sn—O6	144.21 (8)	C19—C18—H18A	109.6
O2—Sn—O6	142.15 (7)	C17—C18—H18B	109.6
O5—Sn—O6	69.87 (8)	C19—C18—H18B	109.6
O7—Sn—O6	75.09 (8)	H18A—C18—H18B	108.1
C1—O1—Sn	117.4 (2)	C18—C19—C20	111.1 (3)
C2—O2—Sn	117.3 (2)	C18—C19—H19A	109.4
C3—O5—Sn	119.8 (2)	C20—C19—H19A	109.4
C3ⁱ—O6—Sn	114.2 (2)	C18—C19—H19B	109.4
Sn—O7—H7A	104 (3)	C20—C19—H19B	109.4
Sn—O7—H7B	127 (3)	H19A—C19—H19B	108.0
H7A—O7—H7B	103 (4)	C21—C20—C19	112.4 (3)
C16—N—C22	118.5 (3)	C21—C20—H20A	109.1
C16—N—H1A	108 (2)	C19—C20—H20A	109.1
C22—N—H1A	105 (2)	C21—C20—H20B	109.1
C16—N—H1B	108 (2)	C19—C20—H20B	109.1
C22—N—H1B	109 (2)	H20A—C20—H20B	107.9
H1A—N—H1B	108 (3)	C20—C21—C16	109.6 (3)
O4—C1—O1	125.1 (3)	C20—C21—H21A	109.8
O4—C1—C2	118.2 (3)	C16—C21—H21A	109.8
O1—C1—C2	116.6 (3)	C20—C21—H21B	109.8
O3—C2—O2	126.6 (3)	C16—C21—H21B	109.8
O3—C2—C1	118.9 (3)	H21A—C21—H21B	108.2
O2—C2—C1	114.4 (3)	N—C22—C23	107.8 (3)
O6ⁱ—C3—O5	125.2 (3)	N—C22—C27	110.8 (3)
O6ⁱ—C3—C3ⁱ	117.5 (4)	C23—C22—C27	111.5 (3)
O5—C3—C3ⁱ	117.2 (4)	N—C22—H22	108.9
C5—C4—C9	117.9 (3)	C23—C22—H22	108.9
C5—C4—Sn	121.4 (2)	C27—C22—H22	108.9
C9—C4—Sn	120.6 (2)	C22—C23—C24	110.6 (3)
C6—C5—C4	121.3 (3)	C22—C23—H23A	109.5
C6—C5—H5	119.4	C24—C23—H23A	109.5
C4—C5—H5	119.4	C22—C23—H23B	109.5
C7—C6—C5	120.2 (3)	C24—C23—H23B	109.5
C7—C6—H6	119.9	H23A—C23—H23B	108.1
C5—C6—H6	119.9	C25—C24—C23	110.9 (3)
C6—C7—C8	119.4 (3)	C25—C24—H24A	109.5
C6—C7—H7	120.3	C23—C24—H24A	109.5
C8—C7—H7	120.3	C25—C24—H24B	109.5
C9—C8—C7	120.7 (3)	C23—C24—H24B	109.5
C9—C8—H8	119.7	H24A—C24—H24B	108.1
C7—C8—H8	119.7	C24—C25—C26	110.5 (3)
C8—C9—C4	120.6 (3)	C24—C25—H25A	109.5
C8—C9—H9	119.7	C26—C25—H25A	109.5
C4—C9—H9	119.7	C24—C25—H25B	109.5
C11—C10—C15	117.5 (3)	C26—C25—H25B	109.5
C11—C10—Sn	120.6 (3)	H25A—C25—H25B	108.1
C15—C10—Sn	121.9 (3)	C25—C26—C27	111.5 (3)
C10—C11—C12	120.7 (4)	C25—C26—H26A	109.3
C10—C11—H11	119.6	C27—C26—H26A	109.3
C12—C11—H11	119.6	C25—C26—H26B	109.3
C13—C12—C11	120.5 (4)	C27—C26—H26B	109.3
C13—C12—H12	119.7	H26A—C26—H26B	108.0
C11—C12—H12	119.7	C22—C27—C26	110.0 (3)
C12—C13—C14	119.8 (4)	C22—C27—H27A	109.7
C12—C13—H13	120.1	C26—C27—H27A	109.7
C14—C13—H13	120.1	C22—C27—H27B	109.7
C13—C14—C15	120.0 (4)	C26—C27—H27B	109.7
C13—C14—H14	120.0	H27A—C27—H27B	108.2
C15—C14—H14	120.0

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O4ⁱⁱ	0.90 (4)	1.77 (4)	2.663 (3)	175 (4)
N—H1A···O3ⁱⁱⁱ	0.84 (4)	2.12 (3)	2.910 (4)	155 (3)
N—H1A···O4ⁱⁱⁱ	0.84 (4)	2.37 (4)	2.986 (4)	130 (3)
N—H1B···O6ⁱ	0.91 (4)	2.08 (4)	2.960 (4)	164 (4)

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

Experimental details

Crystal data
Chemical formula	(C₁₂H₂₄N)₂[Sn₂(C₆H₅)₄(C₂O₄)₃(H₂O)₂]
M_r	1210.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	13.1725 (4), 14.6121 (4), 14.1139 (4)
β (°)	100.869 (2)
V (Å³)	2667.88 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV;Blessing, 1995)
T_min, T_max	0.825, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	48411, 6114, 4069
R_int	0.126
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.082, 1.01
No. of reflections	6114
No. of parameters	341
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.72

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O4ⁱ	0.90 (4)	1.77 (4)	2.663 (3)	175 (4)
N—H1A···O3ⁱⁱ	0.84 (4)	2.12 (3)	2.910 (4)	155 (3)
N—H1A···O4ⁱⁱ	0.84 (4)	2.37 (4)	2.986 (4)	130 (3)
N—H1B···O6ⁱⁱⁱ	0.91 (4)	2.08 (4)	2.960 (4)	164 (4)

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

References

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