Di-μ3-oxido-bis­(μ2-quinaldato-κ2O:O)­bis­(quinaldato-κ2N,O)tetra­kis[di-n-butyl­tin(IV)]

Wang, H.; Yin, H.

doi:10.1107/S1600536807066378

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m197-m198

https://doi.org/10.1107/S1600536807066378

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Di-μ₃-oxido-bis(μ₂-quinaldato-κ²O:O)bis(quinaldato-κ²N,O)tetrakis[di-n-butyltin(IV)]

Hongyun Wang ^a and Handong Yin ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 20 November 2007; accepted 10 December 2007; online 18 December 2007)

The title tetranuclear Sn^IV complex, [Sn₄(C₄H₉)₈(C₁₀H₆NO₂)₄O₂], is a cluster built up by inversion symmetry around the central Sn₂O₂ ring. The coordination geometries of the Sn atoms involved can be classified into two types: the five-coordinate Sn atoms of the central Sn₂O₂ core have a trigonal–bipyramidal geometry, with axial positions occupied by a μ₃-O atom and a μ₂-O atom belonging to the nonchelating quinaldate ligand. The peripheral Sn atoms are six-coordinate, with a distorted octahedral geometry. The methyl group of an n-butyl ligand is disordered over two sites, with occupancies of 0.643 (12) and 0.357 (12).

Related literature

For related tin complexes, see: Ma et al. (2004 ); Tian et al. (2005 ).

Experimental

Crystal data

[Sn₄(C₄H₉)₈(C₁₀H₆NO₂)₄O₂]
M_r = 1652.29
Monoclinic, P 2₁ /n
a = 13.096 (5) Å
b = 12.551 (5) Å
c = 22.278 (9) Å
β = 93.971 (5)°
V = 3653 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 298 (2) K
0.52 × 0.31 × 0.24 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.517, T_max = 0.714
18614 measured reflections
6437 independent reflections
4499 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.127
S = 1.00
6437 reflections
410 parameters
169 restraints
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O5	2.042 (4)
Sn1—O5ⁱ	2.141 (4)
Sn1—O1	2.304 (4)
Sn1—N1	3.184 (5)
Sn2—O5	2.049 (4)
Sn2—O3	2.111 (4)
Sn2—O1	2.488 (4)
Sn2—N2	2.539 (5)

O5—Sn1—C25	110.7 (2)
O5—Sn1—C21	113.6 (2)
C25—Sn1—C21	135.5 (3)
O5—Sn1—O5ⁱ	74.10 (15)
C25—Sn1—O5ⁱ	98.0 (2)
C21—Sn1—O5ⁱ	97.2 (2)
O5—Sn1—O1	72.85 (14)
C25—Sn1—O1	94.3 (2)
C21—Sn1—O1	95.2 (2)
O5ⁱ—Sn1—O1	146.94 (14)
O5—Sn1—N1	129.19 (14)
C25—Sn1—N1	70.85 (19)
C21—Sn1—N1	78.7 (2)
O5ⁱ—Sn1—N1	156.19 (13)
O1—Sn1—N1	56.67 (14)
O5—Sn2—O3	80.36 (15)
O5—Sn2—C29	105.4 (2)
O3—Sn2—C29	103.7 (2)
O5—Sn2—C33	102.6 (2)
O3—Sn2—C33	105.7 (2)
C29—Sn2—C33	142.1 (3)
O5—Sn2—O1	68.81 (14)
O3—Sn2—O1	149.11 (14)
C29—Sn2—O1	83.4 (2)
C33—Sn2—O1	83.5 (2)
O5—Sn2—N2	149.32 (15)
O3—Sn2—N2	69.24 (16)
C29—Sn2—N2	86.3 (2)
C33—Sn2—N2	82.4 (2)
O1—Sn2—N2	141.64 (14)
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807066378/bh2155sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066378/bh2155Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is a cluster containing four Sn atoms (Fig. 1). The whole molecule lies on an inversion center, with a central Sn₂O₂ core. The structure is similar to that previously characterized with 3-hydroxypyridine-2-carboxylate as main ligand (Tian et al., 2005). The three-coordinated µ₃ atom O5 in the Sn₂O₂ ring is bonded to a Bu₂SnO₂N unit. Moreover, the C1 carboxylate group coordinates to each independent Sn atom in a bridging mode (Fig. 2). The geometry of the Sn1 atom in the Sn₂O₂ ring is distorted trigonal-bipyramidal with atoms O1 and O5ⁱ [symmetry code (i): -x + 1, -y + 2, -z] in axial positions, while two n-butyl groups and atom O5 form the equatorial plane. For the Sn2 atoms, six primary bonds are formed: three to the O atoms, two to the C atom of n-butyl groups, and one to the chelating quinoline N atom. Thus, the Sn2 centers display a distorted octahedral coordinated geometry. The Sn—O and Sn—N bond lengths (Table 1) are similar to those observed in related organotin carboxylates (Ma et al., 2004).

Related literature top

For related tin complexes, see: Ma et al. (2004); Tian et al. (2005).

Experimental top

The reaction was carried out under a nitrogen atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were dissolved in ethanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Dibutyltin dichloride (1 mmol) was then added and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1). Yield: 83%; m.p. 426 K. Analysis: calculated for C₇₂H₉₆N₄O₁₀Sn₄: C 52.33, H 5.86, N 3.39%. found: C 52.27, H 5.95, N 3.47%.

Structure description top

For related tin complexes, see: Ma et al. (2004); Tian et al. (2005).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids (H atoms have been omitted for clarity). The 'A' labeled atoms are generated by the symmetry operation -x + 1, -y + 2, -z.
	Fig. 2. In this view the n-butyl groups have been omitted for clarity. Atoms with the suffix 'A' are generated by the symmetry operation -x + 1, -y + 2, -z.

Di-µ₃-oxido-bis(µ₂-quinaldato-κ²O:O)bis(quinaldato- κ²N,O)tetrakis[di-n-butyltin(IV)] top

Crystal data top

[Sn₄(C₄H₉)₈(C₁₀H₆NO₂)₄O₂]	F(000) = 1672
M_r = 1652.29	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 426 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.096 (5) Å	Cell parameters from 5520 reflections
b = 12.551 (5) Å	θ = 2.4–22.8°
c = 22.278 (9) Å	µ = 1.41 mm⁻¹
β = 93.971 (5)°	T = 298 K
V = 3653 (3) Å³	Block, colourless
Z = 2	0.52 × 0.31 × 0.24 mm

Data collection top

Bruker SMART diffractometer	6437 independent reflections
Radiation source: fine-focus sealed tube	4499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.517, T_max = 0.714	k = −14→13
18614 measured reflections	l = −26→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.070P)² + 1.6257P] where P = (F_o² + 2F_c²)/3
6437 reflections	(Δ/σ)_max = 0.001
410 parameters	Δρ_max = 0.92 e Å⁻³
169 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn₄(C₄H₉)₈(C₁₀H₆NO₂)₄O₂]	V = 3653 (3) Å³
M_r = 1652.29	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.096 (5) Å	µ = 1.41 mm⁻¹
b = 12.551 (5) Å	T = 298 K
c = 22.278 (9) Å	0.52 × 0.31 × 0.24 mm
β = 93.971 (5)°

Data collection top

Bruker SMART diffractometer	6437 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4499 reflections with I > 2σ(I)
T_min = 0.517, T_max = 0.714	R_int = 0.042
18614 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	169 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	Δρ_max = 0.92 e Å⁻³
6437 reflections	Δρ_min = −0.49 e Å⁻³
410 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.58177 (3)	0.91100 (3)	0.031663 (18)	0.04351 (14)
Sn2	0.40982 (3)	1.01477 (3)	0.134696 (18)	0.04798 (15)
N1	0.7010 (4)	0.7402 (4)	0.1158 (2)	0.0499 (12)
N2	0.2731 (4)	1.0753 (4)	0.2026 (2)	0.0496 (12)
O1	0.5611 (3)	0.8952 (3)	0.13314 (18)	0.0552 (11)
O2	0.5595 (4)	0.8522 (4)	0.2299 (2)	0.0719 (14)
O3	0.3094 (3)	1.1246 (3)	0.08965 (17)	0.0552 (11)
O4	0.1692 (4)	1.2240 (4)	0.0797 (2)	0.0786 (15)
O5	0.4664 (3)	1.0120 (3)	0.05126 (16)	0.0447 (9)
C1	0.5892 (4)	0.8379 (5)	0.1812 (3)	0.0508 (16)
C2	0.6629 (4)	0.7465 (5)	0.1691 (3)	0.0502 (15)
C3	0.6865 (5)	0.6729 (6)	0.2153 (3)	0.0622 (18)
H3	0.6594	0.6808	0.2526	0.075*
C4	0.7488 (6)	0.5906 (6)	0.2050 (3)	0.069 (2)
H4	0.7640	0.5412	0.2355	0.083*
C5	0.7915 (5)	0.5774 (5)	0.1495 (3)	0.0598 (17)
C6	0.7649 (4)	0.6572 (5)	0.1053 (3)	0.0526 (15)
C7	0.8052 (5)	0.6484 (6)	0.0482 (3)	0.0696 (19)
H7	0.7904	0.6999	0.0189	0.083*
C8	0.8655 (6)	0.5647 (7)	0.0368 (4)	0.079 (2)
H8	0.8904	0.5582	−0.0011	0.095*
C9	0.8916 (6)	0.4870 (7)	0.0806 (4)	0.085 (2)
H9	0.9333	0.4301	0.0714	0.102*
C10	0.8567 (6)	0.4944 (6)	0.1359 (4)	0.081 (2)
H10	0.8762	0.4440	0.1650	0.097*
C11	0.2277 (5)	1.1646 (5)	0.1088 (3)	0.0571 (16)
C12	0.2061 (5)	1.1373 (5)	0.1730 (3)	0.0500 (15)
C13	0.1163 (5)	1.1745 (5)	0.1979 (3)	0.0602 (17)
H13	0.0703	1.2185	0.1760	0.072*
C14	0.0994 (5)	1.1438 (6)	0.2547 (3)	0.0667 (19)
H14	0.0406	1.1670	0.2720	0.080*
C15	0.1684 (5)	1.0780 (6)	0.2880 (3)	0.0601 (17)
C16	0.2572 (5)	1.0449 (5)	0.2604 (3)	0.0518 (15)
C17	0.3286 (6)	0.9802 (6)	0.2931 (3)	0.0681 (19)
H17	0.3881	0.9598	0.2757	0.082*
C18	0.3127 (6)	0.9473 (6)	0.3487 (3)	0.074 (2)
H18	0.3609	0.9040	0.3694	0.089*
C19	0.2245 (7)	0.9772 (7)	0.3759 (4)	0.083 (2)
H19	0.2139	0.9532	0.4145	0.099*
C20	0.1536 (6)	1.0415 (7)	0.3465 (3)	0.077 (2)
H20	0.0951	1.0613	0.3652	0.093*
C21	0.7297 (5)	0.9809 (5)	0.0427 (3)	0.0567 (16)
H21A	0.7774	0.9317	0.0261	0.068*
H21B	0.7288	1.0446	0.0180	0.068*
C22	0.7727 (6)	1.0111 (7)	0.1038 (3)	0.085 (2)
H22A	0.7805	0.9471	0.1280	0.102*
H22B	0.7237	1.0566	0.1222	0.102*
C23	0.8746 (7)	1.0681 (8)	0.1058 (4)	0.103 (3)
H23A	0.9024	1.0704	0.1473	0.124*	0.643 (12)
H23B	0.9212	1.0263	0.0834	0.124*	0.643 (12)
H23C	0.8602	1.1432	0.0992	0.124*	0.357 (12)
H23D	0.9063	1.0618	0.1463	0.124*	0.357 (12)
C24	0.8726 (12)	1.1728 (12)	0.0829 (8)	0.131 (5)	0.643 (12)
H24A	0.9407	1.1940	0.0747	0.196*	0.643 (12)
H24B	0.8465	1.2203	0.1119	0.196*	0.643 (12)
H24C	0.8293	1.1753	0.0464	0.196*	0.643 (12)
C24'	0.9529 (19)	1.033 (2)	0.0654 (12)	0.131 (5)	0.357 (12)
H24D	0.9294	0.9707	0.0440	0.196*	0.357 (12)
H24E	1.0154	1.0176	0.0888	0.196*	0.357 (12)
H24F	0.9648	1.0892	0.0373	0.196*	0.357 (12)
C25	0.5233 (5)	0.7567 (5)	0.0104 (3)	0.0580 (16)
H25A	0.5715	0.7200	−0.0135	0.070*
H25B	0.5193	0.7171	0.0475	0.070*
C26	0.4205 (5)	0.7548 (6)	−0.0231 (4)	0.086 (2)
H26A	0.4267	0.7831	−0.0632	0.103*
H26B	0.3747	0.8011	−0.0028	0.103*
C27	0.3720 (7)	0.6405 (7)	−0.0285 (5)	0.114 (3)
H27A	0.3720	0.6090	0.0113	0.136*
H27B	0.3014	0.6465	−0.0444	0.136*
C28	0.4260 (9)	0.5720 (9)	−0.0665 (6)	0.153 (5)
H28A	0.4157	0.5958	−0.1074	0.230*
H28B	0.4009	0.5005	−0.0634	0.230*
H28C	0.4977	0.5737	−0.0543	0.230*
C29	0.5124 (5)	1.1132 (5)	0.1885 (3)	0.0577 (16)
H29A	0.5268	1.0781	0.2269	0.069*
H29B	0.5764	1.1173	0.1691	0.069*
C30	0.4775 (6)	1.2250 (6)	0.2003 (4)	0.084 (2)
H30A	0.4157	1.2227	0.2219	0.101*
H30B	0.4614	1.2611	0.1623	0.101*
C31	0.5616 (7)	1.2885 (7)	0.2378 (4)	0.100 (3)
H31A	0.5800	1.2495	0.2745	0.119*
H31B	0.6220	1.2927	0.2151	0.119*
C32	0.5318 (10)	1.3937 (9)	0.2531 (6)	0.159 (5)
H32A	0.5133	1.4331	0.2170	0.238*
H32B	0.5878	1.4286	0.2752	0.238*
H32C	0.4742	1.3904	0.2774	0.238*
C33	0.3270 (5)	0.8681 (5)	0.1364 (3)	0.0619 (17)
H33A	0.3613	0.8166	0.1123	0.074*
H33B	0.3317	0.8420	0.1775	0.074*
C34	0.2147 (5)	0.8700 (6)	0.1144 (4)	0.078 (2)
H34A	0.1785	0.9167	0.1404	0.094*
H34B	0.2087	0.9002	0.0742	0.094*
C35	0.1644 (6)	0.7645 (7)	0.1129 (5)	0.108 (3)
H35A	0.1667	0.7366	0.1535	0.130*
H35B	0.2036	0.7166	0.0892	0.130*
C36	0.0566 (8)	0.7635 (10)	0.0878 (6)	0.174 (5)
H36A	0.0230	0.8275	0.0994	0.262*
H36B	0.0221	0.7028	0.1031	0.262*
H36C	0.0548	0.7595	0.0447	0.262*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0420 (2)	0.0421 (3)	0.0458 (2)	−0.00321 (18)	−0.00117 (17)	−0.00413 (18)
Sn2	0.0527 (3)	0.0511 (3)	0.0405 (2)	−0.0060 (2)	0.00546 (18)	−0.00393 (18)
N1	0.053 (3)	0.050 (3)	0.046 (3)	−0.009 (3)	−0.005 (2)	0.007 (2)
N2	0.054 (3)	0.056 (3)	0.040 (3)	0.005 (3)	0.007 (2)	−0.005 (2)
O1	0.058 (3)	0.062 (3)	0.046 (2)	0.007 (2)	0.005 (2)	0.005 (2)
O2	0.089 (4)	0.086 (4)	0.041 (3)	0.006 (3)	0.011 (2)	0.004 (2)
O3	0.063 (3)	0.062 (3)	0.042 (2)	0.006 (2)	0.007 (2)	0.002 (2)
O4	0.082 (3)	0.094 (4)	0.059 (3)	0.030 (3)	0.001 (3)	0.012 (3)
O5	0.048 (2)	0.050 (2)	0.036 (2)	0.0018 (18)	0.0065 (17)	0.0003 (17)
C1	0.045 (3)	0.045 (4)	0.059 (4)	−0.009 (3)	−0.024 (3)	0.005 (3)
C2	0.044 (3)	0.060 (4)	0.045 (4)	−0.012 (3)	−0.006 (3)	0.009 (3)
C3	0.060 (4)	0.077 (5)	0.049 (4)	−0.005 (4)	0.000 (3)	0.012 (3)
C4	0.074 (5)	0.069 (5)	0.062 (5)	0.000 (4)	−0.008 (4)	0.025 (4)
C5	0.052 (4)	0.059 (4)	0.066 (4)	0.001 (3)	−0.014 (3)	0.006 (3)
C6	0.046 (3)	0.056 (4)	0.055 (4)	−0.005 (3)	−0.007 (3)	0.001 (3)
C7	0.068 (5)	0.077 (5)	0.063 (5)	0.001 (4)	0.003 (4)	−0.006 (4)
C8	0.068 (5)	0.089 (6)	0.082 (6)	0.006 (4)	0.010 (4)	−0.015 (5)
C9	0.071 (5)	0.076 (6)	0.107 (7)	0.011 (4)	−0.009 (5)	−0.003 (5)
C10	0.073 (5)	0.077 (6)	0.090 (6)	0.008 (4)	−0.020 (5)	0.016 (5)
C11	0.061 (4)	0.053 (4)	0.056 (4)	−0.002 (3)	−0.004 (3)	−0.010 (3)
C12	0.052 (4)	0.053 (4)	0.045 (3)	0.004 (3)	0.004 (3)	0.002 (3)
C13	0.053 (4)	0.061 (4)	0.067 (4)	0.011 (3)	0.005 (3)	−0.001 (3)
C14	0.055 (4)	0.078 (5)	0.069 (5)	0.004 (4)	0.022 (3)	−0.006 (4)
C15	0.056 (4)	0.067 (5)	0.058 (4)	−0.003 (3)	0.011 (3)	−0.007 (3)
C16	0.053 (4)	0.056 (4)	0.046 (3)	0.000 (3)	0.004 (3)	−0.005 (3)
C17	0.077 (5)	0.070 (5)	0.059 (4)	0.011 (4)	0.009 (4)	0.006 (4)
C18	0.088 (5)	0.083 (5)	0.053 (4)	0.014 (4)	0.005 (4)	0.005 (4)
C19	0.096 (6)	0.097 (6)	0.057 (5)	−0.006 (5)	0.017 (4)	0.012 (4)
C20	0.079 (5)	0.094 (6)	0.062 (5)	−0.002 (5)	0.029 (4)	0.001 (4)
C21	0.049 (4)	0.058 (4)	0.061 (4)	−0.011 (3)	−0.005 (3)	0.003 (3)
C22	0.073 (5)	0.106 (6)	0.075 (5)	−0.034 (4)	−0.001 (4)	−0.002 (4)
C23	0.091 (6)	0.116 (7)	0.099 (6)	−0.042 (5)	−0.022 (5)	0.004 (5)
C24	0.121 (9)	0.125 (10)	0.143 (10)	−0.044 (8)	−0.022 (8)	0.028 (9)
C24'	0.121 (9)	0.125 (10)	0.143 (10)	−0.044 (8)	−0.022 (8)	0.028 (9)
C25	0.061 (4)	0.045 (4)	0.065 (4)	−0.003 (3)	−0.015 (3)	−0.005 (3)
C26	0.069 (5)	0.066 (5)	0.118 (6)	−0.011 (4)	−0.024 (4)	−0.011 (4)
C27	0.096 (6)	0.093 (6)	0.146 (8)	−0.014 (5)	−0.030 (6)	−0.031 (6)
C28	0.160 (11)	0.131 (10)	0.165 (11)	−0.028 (8)	−0.016 (9)	−0.038 (8)
C29	0.058 (4)	0.057 (4)	0.058 (4)	−0.009 (3)	−0.001 (3)	−0.009 (3)
C30	0.068 (4)	0.075 (5)	0.109 (6)	−0.008 (4)	−0.002 (4)	−0.027 (5)
C31	0.105 (6)	0.070 (5)	0.119 (6)	−0.003 (5)	−0.024 (5)	−0.031 (5)
C32	0.164 (11)	0.130 (10)	0.177 (12)	−0.007 (9)	−0.023 (9)	−0.050 (9)
C33	0.057 (4)	0.053 (4)	0.077 (4)	−0.006 (3)	0.010 (3)	−0.002 (3)
C34	0.063 (4)	0.077 (5)	0.094 (5)	−0.021 (4)	−0.002 (4)	0.009 (4)
C35	0.085 (6)	0.085 (6)	0.153 (8)	−0.028 (5)	0.000 (6)	−0.004 (6)
C36	0.120 (9)	0.159 (11)	0.238 (14)	−0.064 (8)	−0.038 (9)	−0.009 (10)

Geometric parameters (Å, º) top

Sn1—O5	2.042 (4)	C21—H21A	0.9700
Sn1—C25	2.124 (6)	C21—H21B	0.9700
Sn1—C21	2.126 (6)	C22—C23	1.512 (9)
Sn1—O5ⁱ	2.141 (4)	C22—H22A	0.9700
Sn1—O1	2.304 (4)	C22—H22B	0.9700
Sn1—N1	3.184 (5)	C23—C24	1.409 (13)
Sn2—O5	2.049 (4)	C23—C24'	1.476 (18)
Sn2—O3	2.111 (4)	C23—H23A	0.9700
Sn2—C29	2.131 (6)	C23—H23B	0.9700
Sn2—C33	2.138 (6)	C23—H23C	0.9700
Sn2—O1	2.488 (4)	C23—H23D	0.9700
Sn2—N2	2.539 (5)	C24—H23C	0.5516
N1—C2	1.322 (7)	C24—H24A	0.9600
N1—C6	1.367 (8)	C24—H24B	0.9600
N2—C12	1.315 (7)	C24—H24C	0.9600
N2—C16	1.373 (8)	C24'—H24D	0.9600
O1—C1	1.321 (7)	C24'—H24E	0.9600
O2—C1	1.191 (7)	C24'—H24F	0.9600
O3—C11	1.281 (8)	C25—C26	1.493 (8)
O4—C11	1.223 (7)	C25—H25A	0.9700
O5—Sn1ⁱ	2.141 (4)	C25—H25B	0.9700
C1—C2	1.535 (9)	C26—C27	1.570 (10)
C2—C3	1.402 (8)	C26—H26A	0.9700
C3—C4	1.346 (9)	C26—H26B	0.9700
C3—H3	0.9300	C27—C28	1.428 (12)
C4—C5	1.402 (10)	C27—H27A	0.9700
C4—H4	0.9300	C27—H27B	0.9700
C5—C10	1.395 (10)	C28—H28A	0.9600
C5—C6	1.429 (9)	C28—H28B	0.9600
C6—C7	1.415 (9)	C28—H28C	0.9600
C7—C8	1.348 (10)	C29—C30	1.506 (8)
C7—H7	0.9300	C29—H29A	0.9700
C8—C9	1.406 (11)	C29—H29B	0.9700
C8—H8	0.9300	C30—C31	1.555 (9)
C9—C10	1.345 (12)	C30—H30A	0.9700
C9—H9	0.9300	C30—H30B	0.9700
C10—H10	0.9300	C31—C32	1.426 (11)
C11—C12	1.517 (9)	C31—H31A	0.9700
C12—C13	1.413 (8)	C31—H31B	0.9700
C13—C14	1.356 (9)	C32—H32A	0.9600
C13—H13	0.9300	C32—H32B	0.9600
C14—C15	1.398 (9)	C32—H32C	0.9600
C14—H14	0.9300	C33—C34	1.518 (8)
C15—C20	1.408 (9)	C33—H33A	0.9700
C15—C16	1.416 (9)	C33—H33B	0.9700
C16—C17	1.403 (9)	C34—C35	1.479 (9)
C17—C18	1.335 (9)	C34—H34A	0.9700
C17—H17	0.9300	C34—H34B	0.9700
C18—C19	1.394 (11)	C35—C36	1.482 (11)
C18—H18	0.9300	C35—H35A	0.9700
C19—C20	1.363 (11)	C35—H35B	0.9700
C19—H19	0.9300	C36—H36A	0.9600
C20—H20	0.9300	C36—H36B	0.9600
C21—C22	1.486 (8)	C36—H36C	0.9600

O5—Sn1—C25	110.7 (2)	C21—C22—H22A	108.5
O5—Sn1—C21	113.6 (2)	C23—C22—H22A	108.5
C25—Sn1—C21	135.5 (3)	C21—C22—H22B	108.5
O5—Sn1—O5ⁱ	74.10 (15)	C23—C22—H22B	108.5
C25—Sn1—O5ⁱ	98.0 (2)	H22A—C22—H22B	107.5
C21—Sn1—O5ⁱ	97.2 (2)	C24—C23—C24'	92.9 (15)
O5—Sn1—O1	72.85 (14)	C24—C23—C22	115.9 (10)
C25—Sn1—O1	94.3 (2)	C24'—C23—C22	119.4 (14)
C21—Sn1—O1	95.2 (2)	C24—C23—H23A	108.3
O5ⁱ—Sn1—O1	146.94 (14)	C24'—C23—H23A	111.0
O5—Sn1—N1	129.19 (14)	C22—C23—H23A	108.3
C25—Sn1—N1	70.85 (19)	C24—C23—H23B	108.3
C21—Sn1—N1	78.7 (2)	C22—C23—H23B	108.3
O5ⁱ—Sn1—N1	156.19 (13)	H23A—C23—H23B	107.4
O1—Sn1—N1	56.67 (14)	C24'—C23—H23C	109.2
O5—Sn2—O3	80.36 (15)	C22—C23—H23C	107.0
O5—Sn2—C29	105.4 (2)	H23A—C23—H23C	100.0
O3—Sn2—C29	103.7 (2)	H23B—C23—H23C	124.7
O5—Sn2—C33	102.6 (2)	C24—C23—H23D	114.2
O3—Sn2—C33	105.7 (2)	C24'—C23—H23D	105.8
C29—Sn2—C33	142.1 (3)	C22—C23—H23D	108.0
O5—Sn2—O1	68.81 (14)	H23B—C23—H23D	101.0
O3—Sn2—O1	149.11 (14)	H23C—C23—H23D	106.7
C29—Sn2—O1	83.4 (2)	C23—C24—H24A	109.5
C33—Sn2—O1	83.5 (2)	H23C—C24—H24A	129.2
O5—Sn2—N2	149.32 (15)	C23—C24—H24B	109.5
O3—Sn2—N2	69.24 (16)	H23C—C24—H24B	80.8
C29—Sn2—N2	86.3 (2)	H24A—C24—H24B	109.5
C33—Sn2—N2	82.4 (2)	C23—C24—H24C	109.5
O1—Sn2—N2	141.64 (14)	H23C—C24—H24C	113.3
C2—N1—C6	118.2 (5)	H24A—C24—H24C	109.5
C2—N1—Sn1	106.8 (4)	H24B—C24—H24C	109.5
C6—N1—Sn1	134.0 (4)	C23—C24'—H24D	109.5
C12—N2—C16	119.7 (5)	C23—C24'—H24E	109.5
C12—N2—Sn2	110.7 (4)	H24D—C24'—H24E	109.5
C16—N2—Sn2	129.4 (4)	C23—C24'—H24F	109.5
C1—O1—Sn1	142.9 (4)	H24D—C24'—H24F	109.5
C1—O1—Sn2	119.6 (4)	H24E—C24'—H24F	109.5
Sn1—O1—Sn2	96.27 (14)	C26—C25—Sn1	115.1 (5)
C11—O3—Sn2	127.2 (4)	C26—C25—H25A	108.5
Sn1—O5—Sn2	121.61 (18)	Sn1—C25—H25A	108.5
Sn1—O5—Sn1ⁱ	105.90 (15)	C26—C25—H25B	108.5
Sn2—O5—Sn1ⁱ	132.19 (19)	Sn1—C25—H25B	108.5
O2—C1—O1	124.5 (6)	H25A—C25—H25B	107.5
O2—C1—C2	121.5 (5)	C25—C26—C27	113.5 (7)
O1—C1—C2	114.0 (6)	C25—C26—H26A	108.9
N1—C2—C3	122.9 (6)	C27—C26—H26A	108.9
N1—C2—C1	118.9 (5)	C25—C26—H26B	108.9
C3—C2—C1	118.2 (6)	C27—C26—H26B	108.9
C4—C3—C2	119.1 (6)	H26A—C26—H26B	107.7
C4—C3—H3	120.5	C28—C27—C26	112.4 (9)
C2—C3—H3	120.5	C28—C27—H27A	109.1
C3—C4—C5	121.6 (6)	C26—C27—H27A	109.1
C3—C4—H4	119.2	C28—C27—H27B	109.1
C5—C4—H4	119.2	C26—C27—H27B	109.1
C10—C5—C4	124.6 (7)	H27A—C27—H27B	107.9
C10—C5—C6	119.8 (7)	C27—C28—H28A	109.5
C4—C5—C6	115.6 (6)	C27—C28—H28B	109.5
N1—C6—C7	118.9 (6)	H28A—C28—H28B	109.5
N1—C6—C5	122.6 (6)	C27—C28—H28C	109.5
C7—C6—C5	118.5 (6)	H28A—C28—H28C	109.5
C8—C7—C6	119.3 (7)	H28B—C28—H28C	109.5
C8—C7—H7	120.4	C30—C29—Sn2	116.8 (5)
C6—C7—H7	120.4	C30—C29—H29A	108.1
C7—C8—C9	121.8 (8)	Sn2—C29—H29A	108.1
C7—C8—H8	119.1	C30—C29—H29B	108.1
C9—C8—H8	119.1	Sn2—C29—H29B	108.1
C10—C9—C8	120.4 (8)	H29A—C29—H29B	107.3
C10—C9—H9	119.8	C29—C30—C31	111.0 (6)
C8—C9—H9	119.8	C29—C30—H30A	109.4
C9—C10—C5	120.2 (7)	C31—C30—H30A	109.4
C9—C10—H10	119.9	C29—C30—H30B	109.4
C5—C10—H10	119.9	C31—C30—H30B	109.4
O4—C11—O3	124.7 (6)	H30A—C30—H30B	108.0
O4—C11—C12	119.1 (6)	C32—C31—C30	114.1 (8)
O3—C11—C12	116.2 (6)	C32—C31—H31A	108.7
N2—C12—C13	123.0 (6)	C30—C31—H31A	108.7
N2—C12—C11	116.3 (5)	C32—C31—H31B	108.7
C13—C12—C11	120.7 (6)	C30—C31—H31B	108.7
C14—C13—C12	117.8 (6)	H31A—C31—H31B	107.6
C14—C13—H13	121.1	C31—C32—H32A	109.5
C12—C13—H13	121.1	C31—C32—H32B	109.5
C13—C14—C15	121.4 (6)	H32A—C32—H32B	109.5
C13—C14—H14	119.3	C31—C32—H32C	109.5
C15—C14—H14	119.3	H32A—C32—H32C	109.5
C14—C15—C20	123.9 (7)	H32B—C32—H32C	109.5
C14—C15—C16	117.6 (6)	C34—C33—Sn2	117.5 (5)
C20—C15—C16	118.5 (7)	C34—C33—H33A	107.9
N2—C16—C17	120.7 (6)	Sn2—C33—H33A	107.9
N2—C16—C15	120.5 (6)	C34—C33—H33B	107.9
C17—C16—C15	118.8 (6)	Sn2—C33—H33B	107.9
C18—C17—C16	121.3 (7)	H33A—C33—H33B	107.2
C18—C17—H17	119.3	C35—C34—C33	114.4 (7)
C16—C17—H17	119.3	C35—C34—H34A	108.7
C17—C18—C19	120.5 (8)	C33—C34—H34A	108.7
C17—C18—H18	119.8	C35—C34—H34B	108.7
C19—C18—H18	119.8	C33—C34—H34B	108.7
C20—C19—C18	120.5 (7)	H34A—C34—H34B	107.6
C20—C19—H19	119.7	C34—C35—C36	115.3 (9)
C18—C19—H19	119.7	C34—C35—H35A	108.4
C19—C20—C15	120.3 (7)	C36—C35—H35A	108.4
C19—C20—H20	119.8	C34—C35—H35B	108.4
C15—C20—H20	119.8	C36—C35—H35B	108.4
C22—C21—Sn1	119.7 (5)	H35A—C35—H35B	107.5
C22—C21—H21A	107.4	C35—C36—H36A	109.5
Sn1—C21—H21A	107.4	C35—C36—H36B	109.5
C22—C21—H21B	107.4	H36A—C36—H36B	109.5
Sn1—C21—H21B	107.4	C35—C36—H36C	109.5
H21A—C21—H21B	106.9	H36A—C36—H36C	109.5
C21—C22—C23	115.2 (7)	H36B—C36—H36C	109.5

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Sn₄(C₄H₉)₈(C₁₀H₆NO₂)₄O₂]
M_r	1652.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.096 (5), 12.551 (5), 22.278 (9)
β (°)	93.971 (5)
V (Å³)	3653 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.52 × 0.31 × 0.24

Data collection
Diffractometer	Bruker SMART
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.517, 0.714
No. of measured, independent and observed [I > 2σ(I)] reflections	18614, 6437, 4499
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.127, 1.00
No. of reflections	6437
No. of parameters	410
No. of restraints	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.49

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Selected geometric parameters (Å, º) top

Sn1—O5	2.042 (4)	Sn2—O5	2.049 (4)
Sn1—O5ⁱ	2.141 (4)	Sn2—O3	2.111 (4)
Sn1—O1	2.304 (4)	Sn2—O1	2.488 (4)
Sn1—N1	3.184 (5)	Sn2—N2	2.539 (5)

O5—Sn1—C25	110.7 (2)	O5—Sn2—O3	80.36 (15)
O5—Sn1—C21	113.6 (2)	O5—Sn2—C29	105.4 (2)
C25—Sn1—C21	135.5 (3)	O3—Sn2—C29	103.7 (2)
O5—Sn1—O5ⁱ	74.10 (15)	O5—Sn2—C33	102.6 (2)
C25—Sn1—O5ⁱ	98.0 (2)	O3—Sn2—C33	105.7 (2)
C21—Sn1—O5ⁱ	97.2 (2)	C29—Sn2—C33	142.1 (3)
O5—Sn1—O1	72.85 (14)	O5—Sn2—O1	68.81 (14)
C25—Sn1—O1	94.3 (2)	O3—Sn2—O1	149.11 (14)
C21—Sn1—O1	95.2 (2)	C29—Sn2—O1	83.4 (2)
O5ⁱ—Sn1—O1	146.94 (14)	C33—Sn2—O1	83.5 (2)
O5—Sn1—N1	129.19 (14)	O5—Sn2—N2	149.32 (15)
C25—Sn1—N1	70.85 (19)	O3—Sn2—N2	69.24 (16)
C21—Sn1—N1	78.7 (2)	C29—Sn2—N2	86.3 (2)
O5ⁱ—Sn1—N1	156.19 (13)	C33—Sn2—N2	82.4 (2)
O1—Sn1—N1	56.67 (14)	O1—Sn2—N2	141.64 (14)

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

References

Ma, C. L., Jiang, Q., Zhang, R. F. & Wang, D. Q. (2004). J. Chem. Soc. Dalton Trans. pp. 1832–1840. CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Siemens (1996). SMART (Version 4.0), SAINT (Version 4.0) and SHELXTL (Version 5.1). Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Tian, G.-R., Zhang, R.-F., Ma, C.-L. & Ng, S. W. (2005). Acta Cryst. E61, m2528–m2530. Web of Science CSD CrossRef IUCr Journals Google Scholar

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