Bis(dicyclo-hexyl-ammonium) μ-oxalato-κO,O:O,O-bis-[aqua-(oxalato-κO,O)diphenyl-stannate(IV)].

The structure of the title compound, (C(12)H(24)N)(2)[Sn(2)(C(6)H(5))(4)(C(2)O(4))(3)(H(2)O)(2)], consists of a bischelating oxalate ion, located on an inversion center, which is linked to two SnPh(2) groups. The coordination sphere of the Sn(IV) ion is completed by a monochelating oxalate anion and a water mol-ecule. The Sn(IV) atoms are thus seven-coordinated. The discrete binuclear units are further connected by hydrogen bonds, leading to a supra-molecular crystal structure. The asymmetric unit contains one half dianion and one (Cy(2)NH(2))(+) 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 = 1210.52

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.082

S = 1.01

6114 reflections

341 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.72 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046738/bh2310Isup2.hkl

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

(C12H24N)2[Sn2(C6H5)4(C2O4)3(H2O)2]	F(000) = 1244
Mr = 1210.52	Dx = 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

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

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(Fo2) + (0.0335P)2 + 0.6086P] where P = (Fo2 + 2Fc2)/3
6114 reflections	(Δ/σ)max = 0.001
341 parameters	Δρmax = 0.54 e Å−3
2 restraints	Δρmin = −0.72 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) ; (iii) .