catena-Poly[[triphenyl­tin(IV)]-μ-2-(2-picolinoylhydrazono)propanoato-κ2O1:O2]

Cui, J.; Qiao, Y.; Ding, L.; Yin, H.

doi:10.1107/S1600536809039981

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1313

https://doi.org/10.1107/S1600536809039981

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catena-Poly[[triphenyltin(IV)]-μ-2-(2-picolinoylhydrazono)propanoato-κ²O¹:O²]

Jichun Cui,^a Yanling Qiao,^a Longhua Ding ^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 21 September 2009; accepted 1 October 2009; online 7 October 2009)

In the title polymeric coordination compound, [Sn(C₆H₅)₃(C₉H₈N₃O₃)]_n, the Sn^IV atom is in a distorted trigonal-bipyramidal geometry, being coordinated by two O atoms from two 2-(2-picolinoylhydrazono)propanoate ligands and three phenyl groups. Adjacent Sn atoms are bridged by the 2-(2-picolinoylhydrazono)propanoate ligand through one carbonyl O atom and one carboxylate O atom, forming a chain structure propagating parallel to [100]. An intramolecular N—H⋯O hydrogen bond is observed.

Related literature

For some organotin(IV) complexes with pyruvic acid isonicotinyl hydrazone, see: Yin et al. (2005 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₉H₈N₃O₃)]
M_r = 556.17
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.2622 (9) Å
b = 11.0105 (12) Å
c = 22.344 (2) Å
V = 2524.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 298 K
0.33 × 0.20 × 0.15 mm

Data collection

Siemens SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.724, T_max = 0.859
10482 measured reflections
4441 independent reflections
3863 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.068
S = 1.00
4441 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 1905 Friedel pairs
Flack parameter: −0.01 (2)

Table 1
Selected bond lengths (Å)

Sn1—O2ⁱ	2.123 (3)
Sn1—O3	2.549 (3)
Sn1—C10	2.130 (4)
Sn1—C16	2.134 (4)
Sn1—C22	2.129 (4)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.99	2.647 (5)	132

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039981/hy2232sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039981/hy2232Isup2.hkl

checkCIF report

Comment top

Recently, we have reported some organotin(IV) complexes with pyruvic acid isonicotinyl hydrazone (Yin et al., 2005). As a part of our ongoing investigations in this field, we have synthesized the title compound and present its crystal structure here.

The title compound (Fig. 1) forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 2-(2-picolinoylhydrazono)propanoate ligand. The Sn^IV atom assumes a distorted trigonal-bipyramidal coordination geometry, with atoms O3 and O2ⁱ in the axial positions [O3—Sn1—O2ⁱ = 175.65 (13)°, symmetry code: (i) x+1, y, z] and the atoms C10, C16 and C22 in the equatorial positions. One of the two Sn—O bond lengths is shorter and the other is longer (Table 1). The complex involves an intramolecular N—H···O hydrogen bond (Table 2).

Related literature top

For some organotin(IV) complexes with pyruvic acid isonicotinyl hydrazone, see: Yin et al. (2005).

Experimental top

The reaction was carried out under nitrogen atmosphere. 2-(2-Picolinoylhydrazono)propanoic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 4 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (v/v 1:1) to yield colorless block crystals of the title compound (yield 78%).

Structure description top

For some organotin(IV) complexes with pyruvic acid isonicotinyl hydrazone, see: Yin 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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound, showing the 50% probability displacement ellipsoids. H atoms have been omitted for clarity. [Symmetry code: (i) x+1, y, z.]

catena-Poly[[triphenyltin(IV)]-µ-2-(2-picolinoylhydrazono)propanoato- κ²O¹:O²] top

Crystal data top

[Sn(C₆H₅)₃(C₉H₈N₃O₃)]	F(000) = 1120
M_r = 556.17	D_x = 1.463 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4196 reflections
a = 10.2622 (9) Å	θ = 2.6–23.1°
b = 11.0105 (12) Å	µ = 1.04 mm⁻¹
c = 22.344 (2) Å	T = 298 K
V = 2524.6 (4) Å³	Block, colorless
Z = 4	0.33 × 0.20 × 0.15 mm

Data collection top

Siemens SMART 1000 CCD diffractometer	4441 independent reflections
Radiation source: fine-focus sealed tube	3863 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.724, T_max = 0.859	k = −13→11
10482 measured reflections	l = −11→26

Refinement top

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0302P)² + 0.4754P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4441 reflections	Δρ_max = 0.50 e Å⁻³
308 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1905 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

Crystal data top

[Sn(C₆H₅)₃(C₉H₈N₃O₃)]	V = 2524.6 (4) Å³
M_r = 556.17	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.2622 (9) Å	µ = 1.04 mm⁻¹
b = 11.0105 (12) Å	T = 298 K
c = 22.344 (2) Å	0.33 × 0.20 × 0.15 mm

Data collection top

Siemens SMART 1000 CCD diffractometer	4441 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3863 reflections with I > 2σ(I)
T_min = 0.724, T_max = 0.859	R_int = 0.033
10482 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.50 e Å⁻³
S = 1.00	Δρ_min = −0.32 e Å⁻³
4441 reflections	Absolute structure: Flack (1983), 1905 Friedel pairs
308 parameters	Absolute structure parameter: −0.01 (2)
0 restraints

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

	x	y	z	U_iso*/U_eq
Sn1	0.44055 (3)	0.91214 (3)	0.881010 (13)	0.04040 (9)
N1	−0.0246 (3)	0.8712 (3)	0.86140 (18)	0.0525 (11)
N2	−0.0091 (4)	0.9927 (4)	0.84881 (17)	0.0500 (11)
H2	−0.0749	1.0367	0.8389	0.060*
N3	0.0110 (4)	1.2185 (4)	0.8083 (2)	0.0679 (13)
O1	−0.2663 (3)	1.0095 (3)	0.84524 (16)	0.0615 (10)
O2	−0.3655 (3)	0.8450 (3)	0.88128 (16)	0.0525 (8)
O3	0.2059 (3)	0.9861 (3)	0.87271 (16)	0.0609 (9)
C1	−0.2661 (4)	0.9054 (5)	0.86320 (18)	0.0470 (11)
C2	−0.1409 (4)	0.8298 (4)	0.8660 (2)	0.0536 (14)
C3	−0.1536 (5)	0.6967 (4)	0.8767 (4)	0.095 (2)
H3A	−0.0689	0.6597	0.8753	0.143*
H3B	−0.2081	0.6617	0.8464	0.143*
H3C	−0.1918	0.6831	0.9153	0.143*
C4	0.1115 (5)	1.0416 (5)	0.8524 (2)	0.0490 (13)
C5	0.1188 (5)	1.1707 (5)	0.8323 (2)	0.0524 (13)
C6	0.2312 (6)	1.2354 (5)	0.8391 (3)	0.0771 (17)
H6	0.3048	1.1992	0.8556	0.092*
C7	0.2344 (7)	1.3558 (6)	0.8210 (3)	0.093 (2)
H7	0.3099	1.4016	0.8256	0.111*
C8	0.1258 (6)	1.4063 (6)	0.7964 (3)	0.0855 (18)
H8	0.1258	1.4865	0.7833	0.103*
C9	0.0156 (6)	1.3348 (6)	0.7914 (3)	0.084 (2)
H9	−0.0593	1.3696	0.7755	0.101*
C10	0.3724 (4)	0.7494 (4)	0.92196 (19)	0.0416 (11)
C11	0.4586 (6)	0.6846 (4)	0.9577 (2)	0.0563 (13)
H11	0.5426	0.7141	0.9633	0.068*
C12	0.4220 (6)	0.5767 (5)	0.9851 (2)	0.0695 (14)
H12	0.4816	0.5342	1.0084	0.083*
C13	0.2987 (7)	0.5332 (5)	0.9778 (3)	0.0774 (18)
H13	0.2736	0.4610	0.9960	0.093*
C14	0.2120 (6)	0.5972 (6)	0.9432 (3)	0.0807 (17)
H14	0.1276	0.5679	0.9383	0.097*
C15	0.2481 (5)	0.7040 (5)	0.9156 (2)	0.0613 (15)
H15	0.1878	0.7460	0.8923	0.074*
C16	0.4224 (4)	0.9300 (4)	0.78627 (17)	0.0401 (10)
C17	0.3600 (5)	0.8390 (4)	0.7544 (2)	0.0567 (13)
H17	0.3265	0.7719	0.7745	0.068*
C18	0.3471 (6)	0.8474 (6)	0.6925 (3)	0.0701 (16)
H18	0.3047	0.7861	0.6715	0.084*
C19	0.3964 (5)	0.9455 (6)	0.6623 (2)	0.0710 (17)
H19	0.3889	0.9502	0.6209	0.085*
C20	0.4566 (6)	1.0359 (5)	0.6933 (2)	0.0681 (15)
H20	0.4886	1.1033	0.6730	0.082*
C21	0.4705 (5)	1.0281 (4)	0.7553 (2)	0.0564 (13)
H21	0.5127	1.0901	0.7759	0.068*
C22	0.4531 (5)	1.0551 (4)	0.94492 (18)	0.0418 (10)
C23	0.5361 (6)	1.1514 (4)	0.9415 (2)	0.0656 (15)
H23	0.5927	1.1580	0.9091	0.079*
C24	0.5371 (7)	1.2402 (5)	0.9860 (3)	0.0850 (19)
H24	0.5938	1.3058	0.9826	0.102*
C25	0.4572 (7)	1.2324 (5)	1.0339 (3)	0.0777 (17)
H25	0.4569	1.2930	1.0629	0.093*
C26	0.3775 (7)	1.1350 (6)	1.0388 (3)	0.085 (2)
H26	0.3244	1.1269	1.0723	0.102*
C27	0.3745 (5)	1.0475 (5)	0.9946 (2)	0.0698 (16)
H27	0.3179	0.9820	0.9986	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03474 (14)	0.04058 (15)	0.04589 (15)	−0.00566 (16)	0.00029 (17)	0.00224 (16)
N1	0.032 (2)	0.054 (2)	0.071 (3)	−0.0004 (16)	−0.0010 (18)	−0.0072 (19)
N2	0.030 (2)	0.060 (3)	0.060 (2)	−0.0003 (18)	−0.0007 (18)	0.001 (2)
N3	0.049 (3)	0.084 (3)	0.070 (3)	−0.009 (2)	−0.006 (2)	0.027 (3)
O1	0.0360 (19)	0.061 (2)	0.088 (3)	0.0008 (16)	0.0023 (18)	0.016 (2)
O2	0.0291 (15)	0.0616 (18)	0.067 (2)	−0.0036 (14)	0.0045 (18)	0.008 (2)
O3	0.0346 (18)	0.068 (2)	0.080 (3)	−0.0012 (16)	−0.002 (2)	−0.004 (2)
C1	0.031 (2)	0.061 (3)	0.048 (3)	−0.008 (3)	−0.0073 (19)	0.002 (3)
C2	0.033 (3)	0.050 (3)	0.077 (4)	0.003 (2)	−0.011 (2)	−0.003 (3)
C3	0.050 (3)	0.057 (3)	0.179 (7)	0.002 (3)	−0.005 (5)	0.012 (4)
C4	0.037 (3)	0.064 (3)	0.047 (3)	−0.011 (2)	0.002 (2)	0.000 (3)
C5	0.036 (3)	0.067 (3)	0.054 (3)	−0.008 (3)	0.002 (2)	−0.002 (3)
C6	0.056 (4)	0.076 (4)	0.100 (5)	−0.008 (3)	−0.005 (3)	0.013 (4)
C7	0.071 (5)	0.091 (5)	0.117 (6)	−0.025 (4)	−0.009 (4)	0.014 (4)
C8	0.077 (4)	0.080 (4)	0.099 (5)	−0.017 (4)	0.001 (4)	0.029 (4)
C9	0.073 (5)	0.089 (5)	0.091 (5)	−0.002 (4)	−0.010 (3)	0.037 (4)
C10	0.040 (3)	0.036 (2)	0.049 (3)	−0.002 (2)	0.009 (2)	−0.003 (2)
C11	0.053 (3)	0.058 (3)	0.058 (3)	−0.002 (3)	0.005 (3)	0.009 (2)
C12	0.081 (4)	0.061 (3)	0.066 (3)	0.010 (4)	0.011 (3)	0.021 (3)
C13	0.087 (5)	0.054 (3)	0.091 (4)	−0.009 (3)	0.021 (4)	0.016 (3)
C14	0.059 (4)	0.070 (4)	0.113 (5)	−0.017 (4)	0.015 (3)	0.009 (4)
C15	0.049 (3)	0.052 (3)	0.083 (4)	−0.006 (3)	0.006 (3)	0.012 (3)
C16	0.031 (2)	0.045 (2)	0.044 (2)	0.004 (2)	−0.0019 (19)	0.000 (2)
C17	0.065 (3)	0.051 (3)	0.054 (3)	−0.002 (3)	0.001 (3)	0.001 (3)
C18	0.071 (4)	0.079 (4)	0.061 (4)	−0.002 (3)	−0.015 (3)	−0.018 (3)
C19	0.068 (4)	0.095 (5)	0.051 (3)	0.010 (3)	−0.009 (3)	0.004 (3)
C20	0.070 (4)	0.074 (4)	0.061 (3)	−0.007 (3)	−0.006 (3)	0.019 (3)
C21	0.059 (4)	0.053 (3)	0.056 (3)	−0.007 (3)	−0.007 (3)	0.007 (2)
C22	0.038 (2)	0.043 (3)	0.045 (2)	0.001 (2)	−0.002 (2)	−0.0001 (18)
C23	0.074 (4)	0.056 (3)	0.067 (3)	−0.017 (3)	0.010 (3)	−0.010 (3)
C24	0.097 (5)	0.062 (4)	0.096 (5)	−0.023 (4)	0.006 (4)	−0.024 (3)
C25	0.090 (5)	0.067 (4)	0.076 (4)	0.002 (4)	−0.011 (4)	−0.030 (3)
C26	0.097 (5)	0.102 (5)	0.055 (3)	−0.003 (4)	0.016 (3)	−0.021 (4)
C27	0.074 (4)	0.074 (4)	0.062 (3)	−0.018 (3)	0.016 (3)	−0.008 (3)

Geometric parameters (Å, º) top

Sn1—O2ⁱ	2.123 (3)	C11—C12	1.388 (7)
Sn1—O3	2.549 (3)	C11—H11	0.9300
Sn1—C10	2.130 (4)	C12—C13	1.363 (8)
Sn1—C16	2.134 (4)	C12—H12	0.9300
Sn1—C22	2.129 (4)	C13—C14	1.373 (8)
N1—C2	1.281 (6)	C13—H13	0.9300
N1—N2	1.377 (5)	C14—C15	1.380 (7)
N2—C4	1.352 (5)	C14—H14	0.9300
N2—H2	0.8600	C15—H15	0.9300
N3—C9	1.336 (7)	C16—C21	1.375 (6)
N3—C5	1.337 (6)	C16—C17	1.387 (6)
O1—C1	1.215 (6)	C17—C18	1.393 (7)
O2—C1	1.283 (5)	C17—H17	0.9300
O2—Sn1ⁱⁱ	2.123 (3)	C18—C19	1.370 (8)
O3—C4	1.232 (5)	C18—H18	0.9300
C1—C2	1.532 (6)	C19—C20	1.360 (7)
C2—C3	1.490 (7)	C19—H19	0.9300
C3—H3A	0.9600	C20—C21	1.395 (6)
C3—H3B	0.9600	C20—H20	0.9300
C3—H3C	0.9600	C21—H21	0.9300
C4—C5	1.492 (7)	C22—C23	1.363 (6)
C5—C6	1.365 (7)	C22—C27	1.376 (6)
C6—C7	1.387 (8)	C23—C24	1.394 (7)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.360 (8)	C24—C25	1.351 (8)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.382 (8)	C25—C26	1.353 (8)
C8—H8	0.9300	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.380 (7)
C10—C15	1.378 (7)	C26—H26	0.9300
C10—C11	1.388 (6)	C27—H27	0.9300

O2ⁱ—Sn1—C22	101.46 (16)	C12—C11—H11	119.3
O2ⁱ—Sn1—C10	90.77 (14)	C10—C11—H11	119.3
C22—Sn1—C10	110.71 (16)	C13—C12—C11	119.9 (5)
O2ⁱ—Sn1—C16	96.70 (14)	C13—C12—H12	120.1
C22—Sn1—C16	127.04 (15)	C11—C12—H12	120.1
C10—Sn1—C16	118.37 (16)	C12—C13—C14	119.3 (5)
O2ⁱ—Sn1—O3	175.65 (13)	C12—C13—H13	120.3
C22—Sn1—O3	82.52 (15)	C14—C13—H13	120.3
C10—Sn1—O3	89.43 (14)	C13—C14—C15	121.0 (6)
C16—Sn1—O3	79.40 (13)	C13—C14—H14	119.5
C2—N1—N2	118.0 (4)	C15—C14—H14	119.5
C4—N2—N1	118.7 (4)	C10—C15—C14	120.7 (5)
C4—N2—H2	120.6	C10—C15—H15	119.6
N1—N2—H2	120.6	C14—C15—H15	119.6
C9—N3—C5	117.5 (5)	C21—C16—C17	118.4 (4)
C1—O2—Sn1ⁱⁱ	124.3 (3)	C21—C16—Sn1	122.8 (3)
C4—O3—Sn1	158.1 (3)	C17—C16—Sn1	118.9 (3)
O1—C1—O2	126.3 (4)	C16—C17—C18	120.4 (5)
O1—C1—C2	121.8 (4)	C16—C17—H17	119.8
O2—C1—C2	111.9 (4)	C18—C17—H17	119.8
N1—C2—C3	116.3 (4)	C19—C18—C17	120.4 (5)
N1—C2—C1	125.8 (4)	C19—C18—H18	119.8
C3—C2—C1	117.9 (4)	C17—C18—H18	119.8
C2—C3—H3A	109.5	C20—C19—C18	119.7 (5)
C2—C3—H3B	109.5	C20—C19—H19	120.2
H3A—C3—H3B	109.5	C18—C19—H19	120.2
C2—C3—H3C	109.5	C19—C20—C21	120.4 (5)
H3A—C3—H3C	109.5	C19—C20—H20	119.8
H3B—C3—H3C	109.5	C21—C20—H20	119.8
O3—C4—N2	123.0 (5)	C16—C21—C20	120.8 (5)
O3—C4—C5	122.9 (4)	C16—C21—H21	119.6
N2—C4—C5	114.0 (5)	C20—C21—H21	119.6
N3—C5—C6	122.6 (5)	C23—C22—C27	117.3 (4)
N3—C5—C4	117.0 (5)	C23—C22—Sn1	125.1 (3)
C6—C5—C4	120.4 (5)	C27—C22—Sn1	117.5 (3)
C5—C6—C7	119.1 (6)	C22—C23—C24	120.7 (5)
C5—C6—H6	120.4	C22—C23—H23	119.7
C7—C6—H6	120.4	C24—C23—H23	119.7
C8—C7—C6	119.3 (6)	C25—C24—C23	121.1 (6)
C8—C7—H7	120.4	C25—C24—H24	119.5
C6—C7—H7	120.4	C23—C24—H24	119.5
C7—C8—C9	118.0 (6)	C24—C25—C26	118.8 (5)
C7—C8—H8	121.0	C24—C25—H25	120.6
C9—C8—H8	121.0	C26—C25—H25	120.6
N3—C9—C8	123.5 (6)	C25—C26—C27	120.6 (6)
N3—C9—H9	118.2	C25—C26—H26	119.7
C8—C9—H9	118.2	C27—C26—H26	119.7
C15—C10—C11	117.6 (5)	C22—C27—C26	121.5 (5)
C15—C10—Sn1	124.4 (4)	C22—C27—H27	119.3
C11—C10—Sn1	118.1 (3)	C26—C27—H27	119.3
C12—C11—C10	121.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.647 (5)	132

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₉H₈N₃O₃)]
M_r	556.17
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	10.2622 (9), 11.0105 (12), 22.344 (2)
V (Å³)	2524.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.33 × 0.20 × 0.15

Data collection
Diffractometer	Siemens SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.724, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	10482, 4441, 3863
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.068, 1.00
No. of reflections	4441
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.32
Absolute structure	Flack (1983), 1905 Friedel pairs
Absolute structure parameter	−0.01 (2)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—O2ⁱ	2.123 (3)	Sn1—C16	2.134 (4)
Sn1—O3	2.549 (3)	Sn1—C22	2.129 (4)
Sn1—C10	2.130 (4)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.647 (5)	132

Acknowledgements

We acknowledge the National Natural Foundation of China (grant No. 20771053), the Scientific Research Fund of Liaocheng University (X081006) and the Students Science and Technology Innovation Fund of Liaocheng University (SRT08031HX2).

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yin, H., Hong, M., Xu, H., Gao, Z., Li, G. & Wang, D. (2005). Eur. J. Inorg. Chem. pp. 4572–4581. Web of Science CSD CrossRef Google Scholar