Tetra­kis(μ2-5-methyl­pyrazine-2-carboxyl­ato)-1:2κ3N1,O:O;2:3κ3O:N1,O;1:2κ2O:O′;3:4κ2O:O′-octa­octyl-1κ2C,2κ2C,3κ2C,4κ2C-di-μ3-oxido-1:2:3κ3O;1:3:4κ3O-tetra­tin(IV)

Gao, Z.; Li, F.

doi:10.1107/S1600536809047345

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1579

doi:10.1107/S1600536809047345

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Tetrakis(μ₂-5-methylpyrazine-2-carboxylato)-1:2κ³N¹,O:O;2:3κ³O:N¹,O;1:2κ²O:O′;3:4κ²O:O′-octaoctyl-1κ²C,2κ²C,3κ²C,4κ²C-di-μ₃-oxido-1:2:3κ³O;1:3:4κ³O-tetratin(IV)

Zhongjun Gao ^a ^* and Fahui Li ^b

^aDepartment of Chemistry, Jining University, Shandong 273155, People's Republic of China, and ^bMarine Drug and Food Institute, Ocean University of China, Qingdao 266003, People's Republic of China
^*Correspondence e-mail: zhongjungao@yahoo.cn

(Received 3 November 2009; accepted 9 November 2009; online 14 November 2009)

The title compound, [Sn₄(C₈H₁₇)₈O₂(C₆H₅N₂O₂)₄], is a tetranuclear Sn^IV complex, built up by inversion symmetry around the central Sn₂O₂ ring. The Sn^IV coordination geometries are distorted SnO₃C₂ trigonal-bipyramidal and distorted SnO₄C₂ octahedral. The three-coordinate μ₃-oxido bridging O atom in the Sn₂O₂ ring is attached to three Sn atoms. All non-H atoms, with the exception of the Sn-bonded octyl groups, lie approximately on a non-crystallographic mirror plane.

Related literature

For biological activity of organotin derivatives of carboxylic acid ligands, see: Gielen et al. (1988 ). For related μ₃-oxo bridged Sn^IV structures, see: Vollano et al. (1984 ); Yin et al. (2003 ).

Experimental

Crystal data

[Sn₄(C₈H₁₇)₈O₂(C₆H₅N₂O₂)₄]
M_r = 1960.97
Triclinic, $[P \overline 1]$
a = 12.406 (4) Å
b = 13.282 (4) Å
c = 16.223 (5) Å
α = 76.623 (4)°
β = 73.361 (4)°
γ = 86.522 (3)°
V = 2491.7 (13) Å³
Z = 1
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 295 K
0.63 × 0.54 × 0.49 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.602, T_max = 0.623
12764 measured reflections
8613 independent reflections
4935 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.223
S = 1.11
8613 reflections
496 parameters
H-atom parameters constrained
Δρ_max = 3.10 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O5	1.993 (6)
Sn1—C21	2.133 (16)
Sn1—C13	2.135 (13)
Sn1—O4ⁱ	2.158 (7)
Sn1—O1	2.202 (6)
Sn2—C37	2.090 (12)
Sn2—C29	2.093 (13)
Sn2—O5ⁱ	2.111 (6)
Sn2—O5	2.151 (6)
Sn2—O1	2.455 (7)
Sn2—O3	2.472 (7)
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker 1998 ); cell refinement: SAINT (Bruker 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047345/si2220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047345/si2220Isup2.hkl

checkCIF report

Comment top

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen, et al., 1988). 2-Methylpyrazine-5-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.

The title compound, (Fig. 1), is a tetranuclear tin(IV) complex containing a total of 110 non-H atoms. The molecule is centrosymmetric with a central core Sn₂O₂; the structure is similar to those seen previously in resemble compounds (Yin et al., 2003). The µ₃-bridging O5 atom in the Sn₂O₂ ring is also attached to a capryl₂SnO₂ unit (capryl is the trivial name of the octyl group). In addition, the carboxylate group coordinates to two Sn atoms in a bridging mode. Sn—O and Sn—C bond lenghts are shown in Table 1.

The geometries of both the exocyclic Sn atoms are distorted trigonal- bipyramidal. For the Sn1, atoms O1 and O7 are in axial positions [O1—Sn1—O4 = 168.0 (3)°] and the C atoms of the two capryl groups and O5 are in equatorial positions. The sum of the equatorial C—Sn—C and O—Sn—C angles is 339°, indicating a significant distortion from coplanarity for these atoms.

The geometry around the endocyclic atom Sn2 is different from that of Sn1 and is a distorted octahedron. Here, O3 and O5 are in axial positions [O3—Sn2—O5 =158.9 (3)°] and the C atoms of the two capryl groups, O5ⁱ [symmetry code: -x + 1, -y + 2, -z + 2] and O1 are in equatorial positions. The sum of the equatorial C—Sn—C and O—Sn—C angles is 353.7°, indicating a significant distortion from coplanarity for these atoms. This distortion may arise because of a short Sn2···N1 contact of 2.829 (6)Å (sum of the van der Waals radii = 3.81 Å). Related µ₃ oxo-bridhed tin(IV) ladder structures were reported by Vollano et al., 1984) (Fig. 2).

Related literature top

For biological activity of organotin derivatives of carboxylic acid ligands, see: Gielen et al. (1988). For related µ₃-oxo bridged Sn^IV structures, see: Vollano et al. (1984); Yin et al. (2003).

Experimental top

A mixture of dicapryltin oxide (2.0 mmol,0.722 g) and 2-methylpyrazine-5-carboxylic acid (2.0 mmol, 0.276 g) in methanol (80 ml) was heated under reflux for 8 h. The obtained clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol (1:1) to yield blocks of (I). Yield 0.804 g, 82%, m.p. 368 K, analysis, calculated for C₈₈H₁₅₆N₈O₁₀Sn₄: C 53.90, H, 8.02; N 5.71%; found: C 53.92, H 8.09, N, 5.76%.

Computing details top

Data collection: SMART (Bruker 1998); cell refinement: SAINT (Bruker 1998); data reduction: SAINT (Bruker 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 30% displacement ellipsoids (H atoms omitted for clarity) and the short Sn···N contacts indicated by dashed lines. Symmetry codes as in Table 1.
	Fig. 2. The same view as in Figure 1, but the n-capryl groups have been omitted for clarity.

Tetrakis(µ₂-5-methylpyrazine-2-carboxylato)- 1:4κ³N¹,O:O;2:3κ³O:N¹,O; 1:2κ²O:O';3:4κ²O:4κO'-octaoctyl- 1κ²C,2κ²C,3κ²C,4κ²C-di-µ₃-oxido- 1:2:3κ³O;1:3:4κ³O-tetratin(IV) top

Crystal data top

[Sn₄(C₈H₁₇)₈O₂(C₆H₅N₂O₂)₄]	Z = 1
M_r = 1960.97	F(000) = 1020
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.406 (4) Å	Cell parameters from 3961 reflections
b = 13.282 (4) Å	θ = 2.2–26.6°
c = 16.223 (5) Å	µ = 1.05 mm⁻¹
α = 76.623 (4)°	T = 295 K
β = 73.361 (4)°	Block, colourless
γ = 86.522 (3)°	0.63 × 0.54 × 0.49 mm
V = 2491.7 (13) Å³

Data collection top

Bruker SMART CCD diffractometer	8613 independent reflections
Radiation source: fine-focus sealed tube	4935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→14
T_min = 0.602, T_max = 0.623	k = −15→15
12764 measured reflections	l = −19→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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0784P)² + 14.9991P] where P = (F_o² + 2F_c²)/3
8613 reflections	(Δ/σ)_max = 0.001
496 parameters	Δρ_max = 3.10 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[Sn₄(C₈H₁₇)₈O₂(C₆H₅N₂O₂)₄]	γ = 86.522 (3)°
M_r = 1960.97	V = 2491.7 (13) Å³
Triclinic, P1	Z = 1
a = 12.406 (4) Å	Mo Kα radiation
b = 13.282 (4) Å	µ = 1.05 mm⁻¹
c = 16.223 (5) Å	T = 295 K
α = 76.623 (4)°	0.63 × 0.54 × 0.49 mm
β = 73.361 (4)°

Data collection top

Bruker SMART CCD diffractometer	8613 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4935 reflections with I > 2σ(I)
T_min = 0.602, T_max = 0.623	R_int = 0.041
12764 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0784P)² + 14.9991P] where P = (F_o² + 2F_c²)/3
8613 reflections	Δρ_max = 3.10 e Å⁻³
496 parameters	Δρ_min = −1.14 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Sn1	0.75921 (6)	1.02020 (5)	1.00407 (5)	0.0425 (3)
Sn2	0.54331 (5)	0.88620 (5)	0.97148 (5)	0.0352 (2)
N1	0.6754 (7)	0.7190 (6)	0.9181 (6)	0.048 (2)
N2	0.8219 (9)	0.5630 (7)	0.8661 (7)	0.064 (3)
N3	0.3417 (7)	0.5913 (7)	0.9200 (7)	0.053 (3)
N4	0.1270 (10)	0.5904 (8)	0.9034 (9)	0.082 (4)
O1	0.7472 (6)	0.8839 (5)	0.9515 (5)	0.0458 (18)
O2	0.9195 (7)	0.8183 (6)	0.9440 (6)	0.065 (2)
O3	0.4103 (6)	0.7570 (5)	0.9680 (5)	0.051 (2)
O4	0.2668 (6)	0.8471 (5)	0.9371 (5)	0.052 (2)
O5	0.6013 (5)	1.0223 (5)	0.9969 (5)	0.0377 (16)
C1	0.8261 (10)	0.8085 (8)	0.9410 (8)	0.050 (3)
C2	0.7819 (10)	0.7240 (9)	0.9119 (8)	0.055 (3)
C3	0.8574 (11)	0.6445 (9)	0.8875 (9)	0.060 (3)
H3	0.9324	0.6488	0.8863	0.072*
C4	0.7144 (10)	0.5611 (9)	0.8713 (8)	0.056 (3)
C5	0.6447 (10)	0.6354 (9)	0.8977 (8)	0.057 (3)
H5	0.5690	0.6284	0.9021	0.068*
C6	0.6730 (12)	0.4696 (10)	0.8488 (10)	0.073 (4)
H6A	0.7351	0.4253	0.8308	0.109*
H6B	0.6389	0.4933	0.8017	0.109*
H6C	0.6185	0.4318	0.8998	0.109*
C7	0.3250 (9)	0.7600 (8)	0.9431 (8)	0.051 (3)
C8	0.2775 (9)	0.6749 (8)	0.9274 (8)	0.051 (3)
C9	0.1718 (11)	0.6705 (9)	0.9178 (9)	0.066 (4)
H9	0.1274	0.7291	0.9218	0.079*
C10	0.1861 (11)	0.5135 (9)	0.8960 (9)	0.059 (3)
C11	0.2959 (10)	0.5123 (9)	0.9025 (9)	0.061 (3)
H11	0.3396	0.4540	0.8943	0.073*
C12	0.1371 (12)	0.4235 (10)	0.8802 (10)	0.075 (4)
H12A	0.1070	0.3754	0.9354	0.112*
H12B	0.1944	0.3902	0.8420	0.112*
H12C	0.0780	0.4464	0.8530	0.112*
C13	0.7885 (12)	0.9313 (11)	1.1232 (9)	0.073 (4)
H13A	0.7954	0.8591	1.1200	0.087*
H13B	0.8596	0.9529	1.1275	0.087*
C14	0.6980 (13)	0.9405 (12)	1.2060 (10)	0.081 (4)
H14A	0.6257	0.9258	1.1993	0.097*
H14B	0.6965	1.0114	1.2126	0.097*
C15	0.7133 (13)	0.8685 (12)	1.2899 (10)	0.086 (5)
H15A	0.7168	0.7976	1.2831	0.104*
H15B	0.7843	0.8846	1.2981	0.104*
C16	0.6188 (15)	0.8776 (13)	1.3717 (11)	0.096 (5)
H16A	0.6163	0.9483	1.3790	0.116*
H16B	0.5477	0.8629	1.3630	0.116*
C17	0.6319 (16)	0.8052 (14)	1.4551 (12)	0.103 (5)
H17A	0.7018	0.8213	1.4650	0.124*
H17B	0.6366	0.7347	1.4474	0.124*
C18	0.5347 (16)	0.8129 (14)	1.5359 (12)	0.110 (6)
H18A	0.4646	0.7974	1.5262	0.132*
H18B	0.5305	0.8830	1.5446	0.132*
C19	0.5503 (17)	0.7374 (16)	1.6189 (13)	0.121 (7)
H19A	0.5559	0.6673	1.6100	0.145*
H19B	0.6194	0.7538	1.6297	0.145*
C20	0.4504 (19)	0.7450 (17)	1.6984 (14)	0.145 (8)
H20A	0.4610	0.6981	1.7501	0.218*
H20B	0.3824	0.7273	1.6879	0.218*
H20C	0.4452	0.8145	1.7070	0.218*
C21	0.8774 (14)	1.0941 (13)	0.8843 (11)	0.098 (5)
H21A	0.9513	1.0669	0.8859	0.117*
H21B	0.8596	1.0736	0.8360	0.117*
C22	0.8853 (17)	1.2086 (15)	0.8628 (13)	0.125 (7)
H22A	0.9007	1.2301	0.9116	0.150*
H22B	0.8127	1.2366	0.8582	0.150*
C23	0.9729 (17)	1.2552 (16)	0.7797 (14)	0.127 (7)
H23A	0.9758	1.3290	0.7758	0.152*
H23B	1.0453	1.2270	0.7848	0.152*
C24	0.9587 (17)	1.2402 (16)	0.6965 (14)	0.125 (7)
H24A	0.8811	1.2543	0.6962	0.150*
H24B	0.9735	1.1683	0.6935	0.150*
C25	1.0353 (18)	1.3088 (16)	0.6151 (15)	0.131 (7)
H25A	1.0141	1.3804	0.6147	0.158*
H25B	1.1120	1.3010	0.6194	0.158*
C26	1.0324 (18)	1.2861 (17)	0.5299 (15)	0.131 (7)
H26A	0.9557	1.2926	0.5260	0.157*
H26B	1.0554	1.2150	0.5296	0.157*
C27	1.108 (2)	1.3568 (18)	0.4499 (16)	0.144 (8)
H27A	1.0823	1.4274	0.4494	0.173*
H27B	1.1834	1.3527	0.4559	0.173*
C28	1.111 (2)	1.3339 (19)	0.3636 (17)	0.166 (10)
H28A	1.1636	1.3801	0.3170	0.249*
H28B	1.0379	1.3431	0.3547	0.249*
H28C	1.1350	1.2637	0.3635	0.249*
C29	0.5414 (11)	0.7814 (10)	1.0901 (9)	0.068 (4)
H29A	0.5512	0.7128	1.0778	0.082*
H29B	0.6074	0.7957	1.1062	0.082*
C30	0.4425 (13)	0.7758 (12)	1.1704 (10)	0.083 (4)
H30A	0.3759	0.7564	1.1576	0.099*
H30B	0.4297	0.8438	1.1837	0.099*
C31	0.4592 (14)	0.6980 (12)	1.2516 (11)	0.089 (5)
H31A	0.4744	0.6306	1.2374	0.107*
H31B	0.5249	0.7187	1.2650	0.107*
C32	0.3609 (15)	0.6884 (13)	1.3323 (11)	0.101 (5)
H32A	0.2954	0.6660	1.3198	0.122*
H32B	0.3446	0.7558	1.3463	0.122*
C33	0.3816 (16)	0.6122 (14)	1.4119 (12)	0.109 (6)
H33A	0.3944	0.5443	1.3984	0.131*
H33B	0.4497	0.6327	1.4219	0.131*
C34	0.2882 (17)	0.6041 (16)	1.4950 (13)	0.121 (6)
H34A	0.2200	0.5815	1.4865	0.145*
H34B	0.2742	0.6717	1.5091	0.145*
C35	0.3176 (18)	0.5265 (16)	1.5727 (14)	0.131 (7)
H35A	0.3170	0.4565	1.5643	0.157*
H35B	0.3924	0.5412	1.5745	0.157*
C36	0.232 (2)	0.5354 (19)	1.6591 (16)	0.169 (10)
H36A	0.2496	0.4865	1.7071	0.253*
H36B	0.1580	0.5211	1.6569	0.253*
H36C	0.2342	0.6042	1.6679	0.253*
C37	0.5683 (10)	0.9247 (10)	0.8349 (8)	0.061 (3)
H37A	0.5380	0.8677	0.8202	0.073*
H37B	0.5208	0.9840	0.8230	0.073*
C38	0.6816 (11)	0.9497 (11)	0.7698 (9)	0.074 (4)
H38A	0.7279	0.8882	0.7735	0.088*
H38B	0.7174	1.0023	0.7858	0.088*
C39	0.6774 (13)	0.9875 (12)	0.6759 (10)	0.086 (4)
H39A	0.6394	0.9350	0.6617	0.104*
H39B	0.6305	1.0487	0.6735	0.104*
C40	0.7846 (15)	1.0136 (14)	0.6054 (11)	0.104 (5)
H40A	0.8313	0.9523	0.6058	0.124*
H40B	0.8238	1.0657	0.6192	0.124*
C41	0.7724 (15)	1.0529 (15)	0.5138 (12)	0.109 (6)
H41A	0.7236	1.0052	0.5040	0.131*
H41B	0.7341	1.1189	0.5121	0.131*
C42	0.8757 (16)	1.0673 (16)	0.4391 (13)	0.120 (7)
H42A	0.9127	1.0009	0.4380	0.144*
H42B	0.9264	1.1131	0.4490	0.144*
C43	0.8560 (17)	1.1118 (17)	0.3492 (13)	0.127 (7)
H43A	0.8058	1.0654	0.3394	0.153*
H43B	0.8178	1.1775	0.3510	0.153*
C44	0.9569 (19)	1.1282 (19)	0.2737 (15)	0.165 (10)
H44A	0.9357	1.1556	0.2204	0.247*
H44B	0.9949	1.0636	0.2701	0.247*
H44C	1.0062	1.1763	0.2811	0.247*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0267 (4)	0.0374 (4)	0.0702 (6)	0.0005 (3)	−0.0202 (4)	−0.0176 (4)
Sn2	0.0282 (4)	0.0306 (4)	0.0502 (5)	−0.0008 (3)	−0.0144 (3)	−0.0113 (3)
N1	0.038 (5)	0.040 (5)	0.078 (7)	0.002 (4)	−0.030 (5)	−0.020 (5)
N2	0.065 (7)	0.048 (6)	0.094 (9)	0.010 (5)	−0.029 (6)	−0.038 (6)
N3	0.038 (5)	0.044 (5)	0.085 (8)	0.000 (4)	−0.028 (5)	−0.017 (5)
N4	0.070 (8)	0.049 (6)	0.152 (12)	0.008 (6)	−0.056 (8)	−0.043 (7)
O1	0.037 (4)	0.036 (4)	0.073 (5)	0.004 (3)	−0.021 (4)	−0.020 (4)
O2	0.046 (5)	0.054 (5)	0.113 (8)	0.004 (4)	−0.037 (5)	−0.035 (5)
O3	0.041 (4)	0.044 (4)	0.083 (6)	−0.003 (3)	−0.031 (4)	−0.023 (4)
O4	0.042 (4)	0.044 (4)	0.083 (6)	−0.002 (4)	−0.031 (4)	−0.023 (4)
O5	0.030 (4)	0.027 (3)	0.064 (5)	−0.003 (3)	−0.025 (3)	−0.010 (3)
C1	0.053 (7)	0.050 (7)	0.062 (8)	−0.013 (6)	−0.022 (6)	−0.033 (6)
C2	0.049 (7)	0.057 (7)	0.072 (9)	0.000 (6)	−0.031 (6)	−0.020 (6)
C3	0.051 (8)	0.057 (8)	0.078 (9)	0.001 (6)	−0.024 (7)	−0.019 (7)
C4	0.053 (8)	0.052 (7)	0.072 (9)	−0.001 (6)	−0.025 (7)	−0.021 (6)
C5	0.053 (8)	0.053 (7)	0.077 (9)	−0.007 (6)	−0.027 (7)	−0.024 (7)
C6	0.075 (10)	0.061 (8)	0.093 (11)	−0.008 (7)	−0.032 (8)	−0.027 (8)
C7	0.040 (6)	0.044 (6)	0.082 (9)	−0.002 (5)	−0.031 (6)	−0.023 (6)
C8	0.044 (7)	0.044 (6)	0.079 (9)	−0.007 (5)	−0.029 (6)	−0.026 (6)
C9	0.055 (8)	0.047 (7)	0.099 (11)	0.010 (6)	−0.022 (7)	−0.025 (7)
C10	0.056 (8)	0.046 (7)	0.087 (10)	−0.004 (6)	−0.028 (7)	−0.025 (7)
C11	0.056 (8)	0.049 (7)	0.087 (10)	−0.001 (6)	−0.028 (7)	−0.024 (7)
C12	0.081 (10)	0.058 (8)	0.102 (12)	−0.011 (7)	−0.041 (9)	−0.029 (8)
C13	0.072 (9)	0.075 (9)	0.080 (10)	0.000 (8)	−0.034 (8)	−0.020 (8)
C14	0.079 (11)	0.084 (10)	0.085 (11)	0.004 (8)	−0.036 (9)	−0.016 (9)
C15	0.086 (11)	0.088 (11)	0.088 (12)	0.000 (9)	−0.032 (10)	−0.015 (9)
C16	0.095 (13)	0.098 (12)	0.094 (13)	−0.002 (10)	−0.030 (11)	−0.014 (10)
C17	0.102 (14)	0.103 (13)	0.099 (14)	−0.003 (11)	−0.028 (11)	−0.012 (11)
C18	0.109 (15)	0.112 (14)	0.103 (15)	−0.006 (12)	−0.026 (12)	−0.011 (12)
C19	0.118 (17)	0.122 (16)	0.109 (16)	−0.007 (13)	−0.022 (13)	−0.008 (13)
C20	0.14 (2)	0.15 (2)	0.121 (18)	−0.015 (16)	−0.015 (15)	−0.012 (15)
C21	0.085 (12)	0.093 (12)	0.103 (13)	−0.013 (10)	−0.011 (10)	−0.015 (10)
C22	0.109 (15)	0.117 (16)	0.120 (17)	−0.015 (13)	−0.002 (13)	−0.005 (13)
C23	0.112 (16)	0.122 (16)	0.120 (18)	−0.017 (13)	−0.005 (14)	−0.005 (14)
C24	0.109 (16)	0.124 (16)	0.119 (18)	−0.017 (13)	−0.008 (14)	−0.007 (14)
C25	0.116 (17)	0.130 (17)	0.122 (18)	−0.016 (14)	−0.008 (14)	−0.003 (15)
C26	0.116 (17)	0.130 (17)	0.120 (18)	−0.015 (14)	−0.007 (14)	−0.006 (15)
C27	0.131 (19)	0.14 (2)	0.13 (2)	−0.016 (16)	−0.008 (16)	−0.004 (17)
C28	0.15 (2)	0.17 (2)	0.14 (2)	−0.020 (18)	−0.001 (18)	−0.008 (19)
C29	0.066 (9)	0.067 (8)	0.080 (10)	−0.002 (7)	−0.029 (8)	−0.019 (7)
C30	0.080 (11)	0.081 (10)	0.089 (12)	0.000 (8)	−0.029 (9)	−0.015 (9)
C31	0.091 (12)	0.089 (11)	0.090 (12)	−0.006 (9)	−0.031 (10)	−0.014 (10)
C32	0.101 (14)	0.098 (13)	0.098 (14)	−0.003 (11)	−0.026 (11)	−0.010 (11)
C33	0.108 (15)	0.108 (14)	0.103 (15)	−0.007 (12)	−0.026 (12)	−0.008 (12)
C34	0.120 (16)	0.118 (16)	0.111 (16)	−0.006 (13)	−0.023 (13)	−0.007 (13)
C35	0.126 (18)	0.128 (17)	0.117 (18)	−0.006 (14)	−0.017 (14)	−0.004 (14)
C36	0.16 (2)	0.17 (2)	0.14 (2)	−0.017 (19)	−0.009 (18)	−0.005 (18)
C37	0.056 (8)	0.062 (8)	0.075 (9)	−0.005 (6)	−0.026 (7)	−0.022 (7)
C38	0.066 (9)	0.075 (9)	0.081 (11)	−0.005 (8)	−0.021 (8)	−0.018 (8)
C39	0.079 (11)	0.094 (11)	0.083 (12)	−0.011 (9)	−0.019 (9)	−0.017 (9)
C40	0.093 (13)	0.108 (14)	0.097 (14)	−0.011 (11)	−0.014 (11)	−0.009 (11)
C41	0.100 (14)	0.115 (14)	0.098 (15)	−0.013 (11)	−0.012 (12)	−0.011 (12)
C42	0.108 (15)	0.125 (16)	0.106 (16)	−0.013 (13)	−0.010 (13)	−0.006 (13)
C43	0.115 (17)	0.135 (18)	0.108 (17)	−0.015 (14)	−0.009 (14)	−0.007 (14)
C44	0.14 (2)	0.18 (2)	0.13 (2)	−0.017 (18)	0.002 (17)	0.002 (17)

Geometric parameters (Å, º) top

Sn1—O5	1.993 (6)	C21—H21B	0.9700
Sn1—C21	2.133 (16)	C22—C23	1.50 (2)
Sn1—C13	2.135 (13)	C22—H22A	0.9700
Sn1—O4ⁱ	2.158 (7)	C22—H22B	0.9700
Sn1—O1	2.202 (6)	C23—C24	1.47 (2)
Sn2—C37	2.090 (12)	C23—H23A	0.9700
Sn2—C29	2.093 (13)	C23—H23B	0.9700
Sn2—O5ⁱ	2.111 (6)	C24—C25	1.52 (2)
Sn2—O5	2.151 (6)	C24—H24A	0.9700
Sn2—O1	2.455 (7)	C24—H24B	0.9700
Sn2—O3	2.472 (7)	C25—C26	1.49 (3)
Sn2—N1	2.829 (9)	C25—H25A	0.9700
N1—C2	1.300 (13)	C25—H25B	0.9700
N1—C5	1.334 (13)	C26—C27	1.51 (3)
N2—C4	1.313 (14)	C26—H26A	0.9700
N2—C3	1.343 (14)	C26—H26B	0.9700
N3—C8	1.334 (13)	C27—C28	1.49 (3)
N3—C11	1.345 (14)	C27—H27A	0.9700
N4—C10	1.229 (15)	C27—H27B	0.9700
N4—C9	1.326 (15)	C28—H28A	0.9600
O1—C1	1.363 (13)	C28—H28B	0.9600
O2—C1	1.189 (12)	C28—H28C	0.9600
O3—C7	1.231 (12)	C29—C30	1.503 (19)
O4—C7	1.326 (12)	C29—H29A	0.9700
O4—Sn1ⁱ	2.158 (7)	C29—H29B	0.9700
O5—Sn2ⁱ	2.111 (6)	C30—C31	1.532 (19)
C1—C2	1.500 (14)	C30—H30A	0.9700
C2—C3	1.418 (16)	C30—H30B	0.9700
C3—H3	0.9300	C31—C32	1.50 (2)
C4—C5	1.336 (16)	C31—H31A	0.9700
C4—C6	1.504 (15)	C31—H31B	0.9700
C5—H5	0.9300	C32—C33	1.52 (2)
C6—H6A	0.9600	C32—H32A	0.9700
C6—H6B	0.9600	C32—H32B	0.9700
C6—H6C	0.9600	C33—C34	1.49 (2)
C7—C8	1.411 (14)	C33—H33A	0.9700
C8—C9	1.370 (15)	C33—H33B	0.9700
C9—H9	0.9300	C34—C35	1.55 (2)
C10—C11	1.395 (16)	C34—H34A	0.9700
C10—C12	1.478 (15)	C34—H34B	0.9700
C11—H11	0.9300	C35—C36	1.52 (3)
C12—H12A	0.9600	C35—H35A	0.9700
C12—H12B	0.9600	C35—H35B	0.9700
C12—H12C	0.9600	C36—H36A	0.9600
C13—C14	1.508 (19)	C36—H36B	0.9600
C13—H13A	0.9700	C36—H36C	0.9600
C13—H13B	0.9700	C37—C38	1.500 (17)
C14—C15	1.526 (19)	C37—H37A	0.9700
C14—H14A	0.9700	C37—H37B	0.9700
C14—H14B	0.9700	C38—C39	1.503 (19)
C15—C16	1.52 (2)	C38—H38A	0.9700
C15—H15A	0.9700	C38—H38B	0.9700
C15—H15B	0.9700	C39—C40	1.48 (2)
C16—C17	1.51 (2)	C39—H39A	0.9700
C16—H16A	0.9700	C39—H39B	0.9700
C16—H16B	0.9700	C40—C41	1.50 (2)
C17—C18	1.52 (2)	C40—H40A	0.9700
C17—H17A	0.9700	C40—H40B	0.9700
C17—H17B	0.9700	C41—C42	1.48 (2)
C18—C19	1.53 (2)	C41—H41A	0.9700
C18—H18A	0.9700	C41—H41B	0.9700
C18—H18B	0.9700	C42—C43	1.52 (2)
C19—C20	1.53 (2)	C42—H42A	0.9700
C19—H19A	0.9700	C42—H42B	0.9700
C19—H19B	0.9700	C43—C44	1.46 (2)
C20—H20A	0.9600	C43—H43A	0.9700
C20—H20B	0.9600	C43—H43B	0.9700
C20—H20C	0.9600	C44—H44A	0.9600
C21—C22	1.48 (2)	C44—H44B	0.9600
C21—H21A	0.9700	C44—H44C	0.9600

O5—Sn1—C21	114.0 (5)	H21A—C21—H21B	107.1
O5—Sn1—C13	116.2 (4)	C21—C22—C23	115.4 (18)
C21—Sn1—C13	129.3 (6)	C21—C22—H22A	108.4
O5—Sn1—O4ⁱ	92.8 (3)	C23—C22—H22A	108.4
C21—Sn1—O4ⁱ	95.7 (5)	C21—C22—H22B	108.4
C13—Sn1—O4ⁱ	88.1 (4)	C23—C22—H22B	108.4
O5—Sn1—O1	75.7 (2)	H22A—C22—H22B	107.5
C21—Sn1—O1	92.0 (5)	C24—C23—C22	117.1 (19)
C13—Sn1—O1	94.2 (4)	C24—C23—H23A	108.0
O4ⁱ—Sn1—O1	168.0 (3)	C22—C23—H23A	108.0
C37—Sn2—C29	152.6 (5)	C24—C23—H23B	108.0
C37—Sn2—O5ⁱ	96.3 (4)	C22—C23—H23B	108.0
C29—Sn2—O5ⁱ	104.8 (4)	H23A—C23—H23B	107.3
C37—Sn2—O5	102.9 (4)	C23—C24—C25	113.4 (19)
C29—Sn2—O5	99.4 (4)	C23—C24—H24A	108.9
O5ⁱ—Sn2—O5	74.7 (3)	C25—C24—H24A	108.9
C37—Sn2—O1	91.0 (4)	C23—C24—H24B	108.9
C29—Sn2—O1	82.9 (4)	C25—C24—H24B	108.9
O5ⁱ—Sn2—O1	142.4 (2)	H24A—C24—H24B	107.7
O5—Sn2—O1	67.8 (2)	C26—C25—C24	114.3 (19)
C37—Sn2—O3	83.7 (4)	C26—C25—H25A	108.7
C29—Sn2—O3	81.0 (4)	C24—C25—H25A	108.7
O5ⁱ—Sn2—O3	84.7 (2)	C26—C25—H25B	108.7
O5—Sn2—O3	158.9 (3)	C24—C25—H25B	108.7
O1—Sn2—O3	132.8 (2)	H25A—C25—H25B	107.6
C37—Sn2—N1	78.1 (4)	C25—C26—C27	113 (2)
C29—Sn2—N1	75.8 (4)	C25—C26—H26A	108.9
O5ⁱ—Sn2—N1	158.1 (2)	C27—C26—H26A	108.9
O5—Sn2—N1	127.1 (2)	C25—C26—H26B	108.9
O1—Sn2—N1	59.3 (2)	C27—C26—H26B	108.9
O3—Sn2—N1	73.7 (2)	H26A—C26—H26B	107.7
C2—N1—C5	114.8 (10)	C28—C27—C26	115 (2)
C2—N1—Sn2	115.7 (7)	C28—C27—H27A	108.5
C5—N1—Sn2	129.5 (7)	C26—C27—H27A	108.5
C4—N2—C3	116.1 (10)	C28—C27—H27B	108.5
C8—N3—C11	116.2 (9)	C26—C27—H27B	108.5
C10—N4—C9	117.3 (11)	H27A—C27—H27B	107.5
C1—O1—Sn1	125.7 (6)	C27—C28—H28A	109.5
C1—O1—Sn2	132.8 (6)	C27—C28—H28B	109.5
Sn1—O1—Sn2	98.3 (3)	H28A—C28—H28B	109.5
C7—O3—Sn2	135.6 (7)	C27—C28—H28C	109.5
C7—O4—Sn1ⁱ	137.4 (7)	H28A—C28—H28C	109.5
Sn1—O5—Sn2ⁱ	137.1 (3)	H28B—C28—H28C	109.5
Sn1—O5—Sn2	116.6 (3)	C30—C29—Sn2	120.7 (9)
Sn2ⁱ—O5—Sn2	105.3 (3)	C30—C29—H29A	107.2
O2—C1—O1	122.6 (9)	Sn2—C29—H29A	107.2
O2—C1—C2	127.3 (11)	C30—C29—H29B	107.2
O1—C1—C2	109.4 (9)	Sn2—C29—H29B	107.2
N1—C2—C3	121.7 (10)	H29A—C29—H29B	106.8
N1—C2—C1	120.5 (11)	C29—C30—C31	112.8 (13)
C3—C2—C1	117.5 (10)	C29—C30—H30A	109.0
N2—C3—C2	120.7 (11)	C31—C30—H30A	109.0
N2—C3—H3	119.6	C29—C30—H30B	109.0
C2—C3—H3	119.6	C31—C30—H30B	109.0
N2—C4—C5	121.5 (10)	H30A—C30—H30B	107.8
N2—C4—C6	116.8 (11)	C32—C31—C30	114.3 (14)
C5—C4—C6	121.6 (11)	C32—C31—H31A	108.7
N1—C5—C4	125.0 (11)	C30—C31—H31A	108.7
N1—C5—H5	117.5	C32—C31—H31B	108.7
C4—C5—H5	117.5	C30—C31—H31B	108.7
C4—C6—H6A	109.5	H31A—C31—H31B	107.6
C4—C6—H6B	109.5	C31—C32—C33	112.7 (15)
H6A—C6—H6B	109.5	C31—C32—H32A	109.0
C4—C6—H6C	109.5	C33—C32—H32A	109.0
H6A—C6—H6C	109.5	C31—C32—H32B	109.0
H6B—C6—H6C	109.5	C33—C32—H32B	109.0
O3—C7—O4	118.4 (9)	H32A—C32—H32B	107.8
O3—C7—C8	125.3 (10)	C34—C33—C32	114.6 (17)
O4—C7—C8	116.1 (9)	C34—C33—H33A	108.6
N3—C8—C9	116.8 (9)	C32—C33—H33A	108.6
N3—C8—C7	117.2 (10)	C34—C33—H33B	108.6
C9—C8—C7	126.0 (11)	C32—C33—H33B	108.6
N4—C9—C8	126.0 (11)	H33A—C33—H33B	107.6
N4—C9—H9	117.0	C33—C34—C35	110.9 (17)
C8—C9—H9	117.0	C33—C34—H34A	109.5
N4—C10—C11	120.5 (11)	C35—C34—H34A	109.5
N4—C10—C12	117.9 (12)	C33—C34—H34B	109.5
C11—C10—C12	121.6 (12)	C35—C34—H34B	109.5
N3—C11—C10	123.1 (11)	H34A—C34—H34B	108.0
N3—C11—H11	118.4	C36—C35—C34	109.5 (19)
C10—C11—H11	118.4	C36—C35—H35A	109.8
C10—C12—H12A	109.5	C34—C35—H35A	109.8
C10—C12—H12B	109.5	C36—C35—H35B	109.8
H12A—C12—H12B	109.5	C34—C35—H35B	109.8
C10—C12—H12C	109.5	H35A—C35—H35B	108.2
H12A—C12—H12C	109.5	C35—C36—H36A	109.5
H12B—C12—H12C	109.5	C35—C36—H36B	109.5
C14—C13—Sn1	114.5 (9)	H36A—C36—H36B	109.5
C14—C13—H13A	108.6	C35—C36—H36C	109.5
Sn1—C13—H13A	108.6	H36A—C36—H36C	109.5
C14—C13—H13B	108.6	H36B—C36—H36C	109.5
Sn1—C13—H13B	108.6	C38—C37—Sn2	123.2 (9)
H13A—C13—H13B	107.6	C38—C37—H37A	106.5
C13—C14—C15	114.1 (13)	Sn2—C37—H37A	106.5
C13—C14—H14A	108.7	C38—C37—H37B	106.5
C15—C14—H14A	108.7	Sn2—C37—H37B	106.5
C13—C14—H14B	108.7	H37A—C37—H37B	106.5
C15—C14—H14B	108.7	C37—C38—C39	113.7 (12)
H14A—C14—H14B	107.6	C37—C38—H38A	108.8
C16—C15—C14	112.7 (13)	C39—C38—H38A	108.8
C16—C15—H15A	109.0	C37—C38—H38B	108.8
C14—C15—H15A	109.0	C39—C38—H38B	108.8
C16—C15—H15B	109.0	H38A—C38—H38B	107.7
C14—C15—H15B	109.0	C40—C39—C38	118.6 (14)
H15A—C15—H15B	107.8	C40—C39—H39A	107.7
C17—C16—C15	113.2 (14)	C38—C39—H39A	107.7
C17—C16—H16A	108.9	C40—C39—H39B	107.7
C15—C16—H16A	108.9	C38—C39—H39B	107.7
C17—C16—H16B	108.9	H39A—C39—H39B	107.1
C15—C16—H16B	108.9	C39—C40—C41	115.1 (15)
H16A—C16—H16B	107.7	C39—C40—H40A	108.5
C16—C17—C18	112.6 (16)	C41—C40—H40A	108.5
C16—C17—H17A	109.1	C39—C40—H40B	108.5
C18—C17—H17A	109.1	C41—C40—H40B	108.5
C16—C17—H17B	109.1	H40A—C40—H40B	107.5
C18—C17—H17B	109.1	C42—C41—C40	118.0 (17)
H17A—C17—H17B	107.8	C42—C41—H41A	107.8
C17—C18—C19	111.0 (16)	C40—C41—H41A	107.8
C17—C18—H18A	109.4	C42—C41—H41B	107.8
C19—C18—H18A	109.4	C40—C41—H41B	107.8
C17—C18—H18B	109.4	H41A—C41—H41B	107.2
C19—C18—H18B	109.4	C41—C42—C43	114.4 (17)
H18A—C18—H18B	108.0	C41—C42—H42A	108.7
C20—C19—C18	109.9 (17)	C43—C42—H42A	108.7
C20—C19—H19A	109.7	C41—C42—H42B	108.7
C18—C19—H19A	109.7	C43—C42—H42B	108.7
C20—C19—H19B	109.7	H42A—C42—H42B	107.6
C18—C19—H19B	109.7	C44—C43—C42	116 (2)
H19A—C19—H19B	108.2	C44—C43—H43A	108.3
C19—C20—H20A	109.5	C42—C43—H43A	108.3
C19—C20—H20B	109.5	C44—C43—H43B	108.3
H20A—C20—H20B	109.5	C42—C43—H43B	108.3
C19—C20—H20C	109.5	H43A—C43—H43B	107.4
H20A—C20—H20C	109.5	C43—C44—H44A	109.5
H20B—C20—H20C	109.5	C43—C44—H44B	109.5
C22—C21—Sn1	118.2 (13)	H44A—C44—H44B	109.5
C22—C21—H21A	107.8	C43—C44—H44C	109.5
Sn1—C21—H21A	107.8	H44A—C44—H44C	109.5
C22—C21—H21B	107.8	H44B—C44—H44C	109.5
Sn1—C21—H21B	107.8

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Sn₄(C₈H₁₇)₈O₂(C₆H₅N₂O₂)₄]
M_r	1960.97
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	12.406 (4), 13.282 (4), 16.223 (5)
α, β, γ (°)	76.623 (4), 73.361 (4), 86.522 (3)
V (Å³)	2491.7 (13)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.63 × 0.54 × 0.49

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.602, 0.623
No. of measured, independent and observed [I > 2σ(I)] reflections	12764, 8613, 4935
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.223, 1.11
No. of reflections	8613
No. of parameters	496
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0784P)² + 14.9991P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	3.10, −1.14

Computer programs: SMART (Bruker 1998), SAINT (Bruker 1998), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Sn1—O5	1.993 (6)	Sn2—C29	2.093 (13)
Sn1—C21	2.133 (16)	Sn2—O5ⁱ	2.111 (6)
Sn1—C13	2.135 (13)	Sn2—O5	2.151 (6)
Sn1—O4ⁱ	2.158 (7)	Sn2—O1	2.455 (7)
Sn1—O1	2.202 (6)	Sn2—O3	2.472 (7)
Sn2—C37	2.090 (12)	Sn2—N1	2.829 (9)

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

We acknowledge the financial support of the Science Foundation of Shandong.

References

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