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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1313.
Published online 2009 October 7. doi:  10.1107/S1600536809039981
PMCID: PMC2971240

catena-Poly[[triphenyl­tin(IV)]-μ-2-(2-picolinoylhydrazono)propanoato-κ2 O 1:O 2]

Abstract

In the title polymeric coordination compound, [Sn(C6H5)3(C9H8N3O3)]n, the SnIV 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 [triangle]).

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Object name is e-65-m1313-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H5)3(C9H8N3O3)]
  • M r = 556.17
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1313-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.068
  • S = 1.00
  • 4441 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.32 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1905 Friedel pairs
  • Flack parameter: −0.01 (2)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039981/hy2232Isup2.hkl

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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 SnIV 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).

Experimental

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%).

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å, and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N).

Figures

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.]

Crystal data

[Sn(C6H5)3(C9H8N3O3)]F(000) = 1120
Mr = 556.17Dx = 1.463 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4196 reflections
a = 10.2622 (9) Åθ = 2.6–23.1°
b = 11.0105 (12) ŵ = 1.04 mm1
c = 22.344 (2) ÅT = 298 K
V = 2524.6 (4) Å3Block, colorless
Z = 40.33 × 0.20 × 0.15 mm

Data collection

Siemens SMART 1000 CCD diffractometer4441 independent reflections
Radiation source: fine-focus sealed tube3863 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.724, Tmax = 0.859k = −13→11
10482 measured reflectionsl = −11→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.068w = 1/[σ2(Fo2) + (0.0302P)2 + 0.4754P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4441 reflectionsΔρmax = 0.50 e Å3
308 parametersΔρmin = −0.32 e Å3
0 restraintsAbsolute structure: Flack (1983), 1905 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)

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

xyzUiso*/Ueq
Sn10.44055 (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)
H2−0.07491.03670.83890.060*
N30.0110 (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)
O30.2059 (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−0.06890.65970.87530.143*
H3B−0.20810.66170.84640.143*
H3C−0.19180.68310.91530.143*
C40.1115 (5)1.0416 (5)0.8524 (2)0.0490 (13)
C50.1188 (5)1.1707 (5)0.8323 (2)0.0524 (13)
C60.2312 (6)1.2354 (5)0.8391 (3)0.0771 (17)
H60.30481.19920.85560.092*
C70.2344 (7)1.3558 (6)0.8210 (3)0.093 (2)
H70.30991.40160.82560.111*
C80.1258 (6)1.4063 (6)0.7964 (3)0.0855 (18)
H80.12581.48650.78330.103*
C90.0156 (6)1.3348 (6)0.7914 (3)0.084 (2)
H9−0.05931.36960.77550.101*
C100.3724 (4)0.7494 (4)0.92196 (19)0.0416 (11)
C110.4586 (6)0.6846 (4)0.9577 (2)0.0563 (13)
H110.54260.71410.96330.068*
C120.4220 (6)0.5767 (5)0.9851 (2)0.0695 (14)
H120.48160.53421.00840.083*
C130.2987 (7)0.5332 (5)0.9778 (3)0.0774 (18)
H130.27360.46100.99600.093*
C140.2120 (6)0.5972 (6)0.9432 (3)0.0807 (17)
H140.12760.56790.93830.097*
C150.2481 (5)0.7040 (5)0.9156 (2)0.0613 (15)
H150.18780.74600.89230.074*
C160.4224 (4)0.9300 (4)0.78627 (17)0.0401 (10)
C170.3600 (5)0.8390 (4)0.7544 (2)0.0567 (13)
H170.32650.77190.77450.068*
C180.3471 (6)0.8474 (6)0.6925 (3)0.0701 (16)
H180.30470.78610.67150.084*
C190.3964 (5)0.9455 (6)0.6623 (2)0.0710 (17)
H190.38890.95020.62090.085*
C200.4566 (6)1.0359 (5)0.6933 (2)0.0681 (15)
H200.48861.10330.67300.082*
C210.4705 (5)1.0281 (4)0.7553 (2)0.0564 (13)
H210.51271.09010.77590.068*
C220.4531 (5)1.0551 (4)0.94492 (18)0.0418 (10)
C230.5361 (6)1.1514 (4)0.9415 (2)0.0656 (15)
H230.59271.15800.90910.079*
C240.5371 (7)1.2402 (5)0.9860 (3)0.0850 (19)
H240.59381.30580.98260.102*
C250.4572 (7)1.2324 (5)1.0339 (3)0.0777 (17)
H250.45691.29301.06290.093*
C260.3775 (7)1.1350 (6)1.0388 (3)0.085 (2)
H260.32441.12691.07230.102*
C270.3745 (5)1.0475 (5)0.9946 (2)0.0698 (16)
H270.31790.98200.99860.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.03474 (14)0.04058 (15)0.04589 (15)−0.00566 (16)0.00029 (17)0.00224 (16)
N10.032 (2)0.054 (2)0.071 (3)−0.0004 (16)−0.0010 (18)−0.0072 (19)
N20.030 (2)0.060 (3)0.060 (2)−0.0003 (18)−0.0007 (18)0.001 (2)
N30.049 (3)0.084 (3)0.070 (3)−0.009 (2)−0.006 (2)0.027 (3)
O10.0360 (19)0.061 (2)0.088 (3)0.0008 (16)0.0023 (18)0.016 (2)
O20.0291 (15)0.0616 (18)0.067 (2)−0.0036 (14)0.0045 (18)0.008 (2)
O30.0346 (18)0.068 (2)0.080 (3)−0.0012 (16)−0.002 (2)−0.004 (2)
C10.031 (2)0.061 (3)0.048 (3)−0.008 (3)−0.0073 (19)0.002 (3)
C20.033 (3)0.050 (3)0.077 (4)0.003 (2)−0.011 (2)−0.003 (3)
C30.050 (3)0.057 (3)0.179 (7)0.002 (3)−0.005 (5)0.012 (4)
C40.037 (3)0.064 (3)0.047 (3)−0.011 (2)0.002 (2)0.000 (3)
C50.036 (3)0.067 (3)0.054 (3)−0.008 (3)0.002 (2)−0.002 (3)
C60.056 (4)0.076 (4)0.100 (5)−0.008 (3)−0.005 (3)0.013 (4)
C70.071 (5)0.091 (5)0.117 (6)−0.025 (4)−0.009 (4)0.014 (4)
C80.077 (4)0.080 (4)0.099 (5)−0.017 (4)0.001 (4)0.029 (4)
C90.073 (5)0.089 (5)0.091 (5)−0.002 (4)−0.010 (3)0.037 (4)
C100.040 (3)0.036 (2)0.049 (3)−0.002 (2)0.009 (2)−0.003 (2)
C110.053 (3)0.058 (3)0.058 (3)−0.002 (3)0.005 (3)0.009 (2)
C120.081 (4)0.061 (3)0.066 (3)0.010 (4)0.011 (3)0.021 (3)
C130.087 (5)0.054 (3)0.091 (4)−0.009 (3)0.021 (4)0.016 (3)
C140.059 (4)0.070 (4)0.113 (5)−0.017 (4)0.015 (3)0.009 (4)
C150.049 (3)0.052 (3)0.083 (4)−0.006 (3)0.006 (3)0.012 (3)
C160.031 (2)0.045 (2)0.044 (2)0.004 (2)−0.0019 (19)0.000 (2)
C170.065 (3)0.051 (3)0.054 (3)−0.002 (3)0.001 (3)0.001 (3)
C180.071 (4)0.079 (4)0.061 (4)−0.002 (3)−0.015 (3)−0.018 (3)
C190.068 (4)0.095 (5)0.051 (3)0.010 (3)−0.009 (3)0.004 (3)
C200.070 (4)0.074 (4)0.061 (3)−0.007 (3)−0.006 (3)0.019 (3)
C210.059 (4)0.053 (3)0.056 (3)−0.007 (3)−0.007 (3)0.007 (2)
C220.038 (2)0.043 (3)0.045 (2)0.001 (2)−0.002 (2)−0.0001 (18)
C230.074 (4)0.056 (3)0.067 (3)−0.017 (3)0.010 (3)−0.010 (3)
C240.097 (5)0.062 (4)0.096 (5)−0.023 (4)0.006 (4)−0.024 (3)
C250.090 (5)0.067 (4)0.076 (4)0.002 (4)−0.011 (4)−0.030 (3)
C260.097 (5)0.102 (5)0.055 (3)−0.003 (4)0.016 (3)−0.021 (4)
C270.074 (4)0.074 (4)0.062 (3)−0.018 (3)0.016 (3)−0.008 (3)

Geometric parameters (Å, °)

Sn1—O2i2.123 (3)C11—C121.388 (7)
Sn1—O32.549 (3)C11—H110.9300
Sn1—C102.130 (4)C12—C131.363 (8)
Sn1—C162.134 (4)C12—H120.9300
Sn1—C222.129 (4)C13—C141.373 (8)
N1—C21.281 (6)C13—H130.9300
N1—N21.377 (5)C14—C151.380 (7)
N2—C41.352 (5)C14—H140.9300
N2—H20.8600C15—H150.9300
N3—C91.336 (7)C16—C211.375 (6)
N3—C51.337 (6)C16—C171.387 (6)
O1—C11.215 (6)C17—C181.393 (7)
O2—C11.283 (5)C17—H170.9300
O2—Sn1ii2.123 (3)C18—C191.370 (8)
O3—C41.232 (5)C18—H180.9300
C1—C21.532 (6)C19—C201.360 (7)
C2—C31.490 (7)C19—H190.9300
C3—H3A0.9600C20—C211.395 (6)
C3—H3B0.9600C20—H200.9300
C3—H3C0.9600C21—H210.9300
C4—C51.492 (7)C22—C231.363 (6)
C5—C61.365 (7)C22—C271.376 (6)
C6—C71.387 (8)C23—C241.394 (7)
C6—H60.9300C23—H230.9300
C7—C81.360 (8)C24—C251.351 (8)
C7—H70.9300C24—H240.9300
C8—C91.382 (8)C25—C261.353 (8)
C8—H80.9300C25—H250.9300
C9—H90.9300C26—C271.380 (7)
C10—C151.378 (7)C26—H260.9300
C10—C111.388 (6)C27—H270.9300
O2i—Sn1—C22101.46 (16)C12—C11—H11119.3
O2i—Sn1—C1090.77 (14)C10—C11—H11119.3
C22—Sn1—C10110.71 (16)C13—C12—C11119.9 (5)
O2i—Sn1—C1696.70 (14)C13—C12—H12120.1
C22—Sn1—C16127.04 (15)C11—C12—H12120.1
C10—Sn1—C16118.37 (16)C12—C13—C14119.3 (5)
O2i—Sn1—O3175.65 (13)C12—C13—H13120.3
C22—Sn1—O382.52 (15)C14—C13—H13120.3
C10—Sn1—O389.43 (14)C13—C14—C15121.0 (6)
C16—Sn1—O379.40 (13)C13—C14—H14119.5
C2—N1—N2118.0 (4)C15—C14—H14119.5
C4—N2—N1118.7 (4)C10—C15—C14120.7 (5)
C4—N2—H2120.6C10—C15—H15119.6
N1—N2—H2120.6C14—C15—H15119.6
C9—N3—C5117.5 (5)C21—C16—C17118.4 (4)
C1—O2—Sn1ii124.3 (3)C21—C16—Sn1122.8 (3)
C4—O3—Sn1158.1 (3)C17—C16—Sn1118.9 (3)
O1—C1—O2126.3 (4)C16—C17—C18120.4 (5)
O1—C1—C2121.8 (4)C16—C17—H17119.8
O2—C1—C2111.9 (4)C18—C17—H17119.8
N1—C2—C3116.3 (4)C19—C18—C17120.4 (5)
N1—C2—C1125.8 (4)C19—C18—H18119.8
C3—C2—C1117.9 (4)C17—C18—H18119.8
C2—C3—H3A109.5C20—C19—C18119.7 (5)
C2—C3—H3B109.5C20—C19—H19120.2
H3A—C3—H3B109.5C18—C19—H19120.2
C2—C3—H3C109.5C19—C20—C21120.4 (5)
H3A—C3—H3C109.5C19—C20—H20119.8
H3B—C3—H3C109.5C21—C20—H20119.8
O3—C4—N2123.0 (5)C16—C21—C20120.8 (5)
O3—C4—C5122.9 (4)C16—C21—H21119.6
N2—C4—C5114.0 (5)C20—C21—H21119.6
N3—C5—C6122.6 (5)C23—C22—C27117.3 (4)
N3—C5—C4117.0 (5)C23—C22—Sn1125.1 (3)
C6—C5—C4120.4 (5)C27—C22—Sn1117.5 (3)
C5—C6—C7119.1 (6)C22—C23—C24120.7 (5)
C5—C6—H6120.4C22—C23—H23119.7
C7—C6—H6120.4C24—C23—H23119.7
C8—C7—C6119.3 (6)C25—C24—C23121.1 (6)
C8—C7—H7120.4C25—C24—H24119.5
C6—C7—H7120.4C23—C24—H24119.5
C7—C8—C9118.0 (6)C24—C25—C26118.8 (5)
C7—C8—H8121.0C24—C25—H25120.6
C9—C8—H8121.0C26—C25—H25120.6
N3—C9—C8123.5 (6)C25—C26—C27120.6 (6)
N3—C9—H9118.2C25—C26—H26119.7
C8—C9—H9118.2C27—C26—H26119.7
C15—C10—C11117.6 (5)C22—C27—C26121.5 (5)
C15—C10—Sn1124.4 (4)C22—C27—H27119.3
C11—C10—Sn1118.1 (3)C26—C27—H27119.3
C12—C11—C10121.4 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.992.647 (5)132

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2232).

References

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography