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Acta Cryst. (2007). E63, m2329    [ doi:10.1107/S1600536807038792 ]

Poly[[mu]2-chlorido-nonamethyl-[mu]3-nitrato-tritin(IV)]

Sadiq-ur-Rehman, S. Sherzaman, S. Ali, S. Shahzadi and M. Helliwell

Abstract top

The crystal structure of the title compound, [Sn3(CH3)9Cl(NO3)], contains trigonal-bipyramidal Sn atoms with three methyl groups bonded in the equatorial plane and an O atom of the NO3 group and a Cl atom in the axial sites. The Cl atom, which lies on a threefold axis, is bridged between three Sn atoms, with Sn-Cl distances of 2.9298 (13) Å. The N atom of the NO3 group also lies on a threefold axis, with its O atoms bonded to three Sn atoms. Thus, polymeric sheets are formed parallel to the ab plane.

Comment top

The synthesis and structural chemistry of organotin compounds are fertile areas of research because of their extensive biological and pharmaceutical applications (Anderson et al., 1984). The biological applications of organotin compounds as antitumour and anticancer agents (Gielen, 1994; de Vos et al., 1998) have been well documented. We report here the crystal structure of the title compound (I), in a continuation of our efforts in the synthesis and structural characterization of organotin complexes (Shahzadi et al., 2006). The polymeric structure of (I) which contains trigonal bipyramidal Sn atoms is shown in Fig. 1. The Sn atom is bonded to three methyl groups in equatorial positions with Sn—C distances in the range of 2.127 (9)–2.138 (11) Å. In the axial direction, the Sn atom is bonded to a nitrate O atom and a Cl atom. The nitrate N and the Cl atoms each lie on 3-fold axes. The structure forms polymeric sheets parallel to the ab plane, Fig. 1 and 2.

Related literature top

For related literature, see: Anderson et al. (1984); Gielen (1994); Shahzadi et al. (2006); de Vos et al. (1998).

Experimental top

4-Hydroxy piperidine (1 mmol) and trimethyltin chloride (1 mmol) were suspended in dry methanol (150 ml) in a round bottom two necked flask. The mixture was stirred at room temperature. Solid product obtained was filtered off and recrystallized from chloroform to obtain colourless crystals suitable for X-ray analysis (yield 80°; m.p. 59 °C).

Refinement top

Methyl H atoms were included in calculated positions using the riding method, with C—H distances of 0.96 Å, Uiso(H) = 1.5Ueq(C) and torsion angles optimized to give the best fit to the electron density.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Structure of (I) showing part of a polymeric sheet with atoms of the asymmetric unit labelled. Dashed lines indicate long Sn—Cl bonds. H atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing of (I) viewed down the a axis showing the polymeric sheets parallel to the ab plane. Dashed lines indicate long Sn—Cl bonds. H atoms are omitted for clarity.
Poly[µ2-chlorido-nonamethyl-µ3-nitrato-tritin(IV)] top
Crystal data top
[Sn3(CH3)9Cl(NO3)]Dx = 2.114 Mg m−3
Mr = 588.84Mo Kα radiation, λ = 0.71069 Å
Trigonal, R3Cell parameters from 2484 reflections
Hall symbol: -R 3θ = 2.7–26.4°
a = 9.843 (4) ŵ = 4.16 mm−1
c = 33.073 (5) ÅT = 100 K
V = 2775.0 (12) Å3Plate, colourless
Z = 60.35 × 0.30 × 0.10 mm
F(000) = 1674
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		1282 independent reflections
Radiation source: fine-focus sealed tube1240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −12→12
Tmin = 0.360, Tmax = 1.000k = −10→12
5290 measured reflectionsl = −40→36
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0707P)2 + 62.3389P]
where P = (Fo2 + 2Fc2)/3
1282 reflections(Δ/σ)max < 0.001
56 parametersΔρmax = 4.50 e Å−3
0 restraintsΔρmin = −1.38 e Å−3
Crystal data top
[Sn3(CH3)9Cl(NO3)]Z = 6
Mr = 588.84Mo Kα radiation
Trigonal, R3µ = 4.16 mm−1
a = 9.843 (4) ÅT = 100 K
c = 33.073 (5) Å0.35 × 0.30 × 0.10 mm
V = 2775.0 (12) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		1282 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1240 reflections with I > 2σ(I)
Tmin = 0.360, Tmax = 1.000Rint = 0.040
5290 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0707P)2 + 62.3389P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131Δρmax = 4.50 e Å−3
S = 1.17Δρmin = −1.38 e Å−3
1282 reflectionsAbsolute structure: ?
56 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
xyzUiso*/Ueq
Sn10.10596 (7)0.32791 (9)0.08605 (2)0.0215 (2)
Cl10.00000.00000.06588 (14)0.0316 (10)
O10.1849 (8)0.5680 (8)0.1007 (2)0.0246 (14)
N10.33330.66670.1019 (4)0.025 (3)
C1−0.1303 (13)0.2811 (11)0.0814 (3)0.031 (2)
H1A−0.13170.36580.06740.046*
H1B−0.17340.27120.10800.046*
H1C−0.19200.18520.06670.046*
C20.1779 (12)0.2725 (12)0.1413 (3)0.023 (2)
H2A0.27000.26460.13670.035*
H2B0.09510.17430.15140.035*
H2C0.20100.35370.16080.035*
C30.2335 (13)0.3779 (13)0.0307 (3)0.027 (2)
H3A0.33620.39310.03590.041*
H3B0.24300.47140.01890.041*
H3C0.17880.29160.01230.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0180 (4)0.0224 (4)0.0251 (3)0.0109 (3)−0.0007 (2)−0.0006 (2)
Cl10.0258 (14)0.0258 (14)0.043 (2)0.0129 (7)0.0000.000
O10.015 (3)0.015 (3)0.043 (4)0.007 (3)0.001 (3)−0.002 (3)
N10.029 (5)0.029 (5)0.015 (6)0.015 (3)0.0000.000
C10.029 (6)0.018 (5)0.044 (6)0.011 (4)−0.005 (5)0.000 (4)
C20.020 (5)0.020 (5)0.031 (5)0.010 (4)−0.003 (4)−0.003 (4)
C30.031 (6)0.028 (5)0.026 (5)0.017 (5)−0.003 (4)−0.004 (4)
Geometric parameters (Å, º) top
Sn1—C22.127 (9)C1—H1B0.9600
Sn1—C32.134 (10)C1—H1C0.9600
Sn1—C12.138 (11)C2—H2A0.9600
Sn1—O12.142 (7)C2—H2B0.9600
Sn1—Cl12.9298 (13)C2—H2C0.9600
O1—N11.288 (7)C3—H3A0.9600
N1—O1i1.288 (7)C3—H3B0.9600
N1—O1ii1.288 (7)C3—H3C0.9600
C1—H1A0.9600
C2—Sn1—C3124.3 (4)H1A—C1—H1B109.5
C2—Sn1—C1118.2 (4)Sn1—C1—H1C109.5
C3—Sn1—C1116.0 (4)H1A—C1—H1C109.5
C2—Sn1—O196.0 (3)H1B—C1—H1C109.5
C3—Sn1—O195.3 (3)Sn1—C2—H2A109.5
C1—Sn1—O190.6 (3)Sn1—C2—H2B109.5
C2—Sn1—Cl183.9 (3)H2A—C2—H2B109.5
C3—Sn1—Cl184.4 (3)Sn1—C2—H2C109.5
C1—Sn1—Cl189.8 (3)H2A—C2—H2C109.5
O1—Sn1—Cl1179.64 (19)H2B—C2—H2C109.5
N1—O1—Sn1119.2 (4)Sn1—C3—H3A109.5
O1i—N1—O1ii119.91 (8)Sn1—C3—H3B109.5
O1i—N1—O1119.91 (8)H3A—C3—H3B109.5
O1ii—N1—O1119.91 (8)Sn1—C3—H3C109.5
Sn1—C1—H1A109.5H3A—C3—H3C109.5
Sn1—C1—H1B109.5H3B—C3—H3C109.5
C2—Sn1—O1—N171.1 (9)Sn1—O1—N1—O1i−11.0 (17)
C3—Sn1—O1—N1−54.3 (9)Sn1—O1—N1—O1ii163.0 (7)
C1—Sn1—O1—N1−170.5 (9)
Symmetry codes: (i) −y+1, x−y+1, z; (ii) −x+y, −x+1, z.
Selected bond lengths (Å) top
Sn1—C22.127 (9)Sn1—O12.142 (7)
Sn1—C32.134 (10)Sn1—Cl12.9298 (13)
Sn1—C12.138 (11)
Acknowledgements top

SA is thankful to Quaid-i-Azam University, Islamabad, Pakistan, for financial support.

references
References top

Anderson, K. E., Simionatto, C. S., Drummond, G. S. & Kappas, A. (1984). J. Pharmacol. Exp. Ther. 228, 327–329.

Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison, Wisconsin, USA.

Gielen, M. (1994). Main Group Met. Chem. 17, 1–8.

Shahzadi, S., Ali, S., Bhatti, M. H., Fettouhi, M. & Athar, M. (2006). J. Organomet. Chem. 691, 1797–1802.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Vos, D. de, Willem, R., Gielen, M., van Wingerden, K. E. & Nooter, K. (1998). Met.-Based Drugs, 5, 179–188.