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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m92.
Published online 2009 December 24. doi:  10.1107/S1600536809054403
PMCID: PMC2980015

catena-Poly[[trimethyl­tin(IV)]-μ-cyclo­hex-3-ene-1-carboxyl­ato]

Abstract

The title compound, [Sn(CH3)3(C7H9O2)]n, forms an extended zigzag chain structure propagating parallel to [010]. The Sn atom is in a slightly distorted trigonal-bipyramidal coordination environment with two carboxyl­ate O atoms in the axial and the three methyl groups in equatorial sites. The cyclo­hexene ring has a distorted half-boat conformation. There is an intra­molecular C—H(...)O hydrogen bond.

Related literature

For related structures, see: Murugavel et al. (2001 [triangle]); Ma et al. (2006 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]).

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Object name is e-66-00m92-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)3(C7H9O2)]
  • M r = 288.93
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m92-efi1.jpg
  • a = 11.3022 (15) Å
  • b = 9.8469 (14) Å
  • c = 12.1468 (18) Å
  • β = 112.148 (2)°
  • V = 1252.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.01 mm−1
  • T = 298 K
  • 0.45 × 0.36 × 0.33 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.464, T max = 0.556
  • 6095 measured reflections
  • 2193 independent reflections
  • 1669 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.101
  • S = 1.08
  • 2193 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 1.53 e Å−3
  • Δρmin = −0.49 e Å−3

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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054403/bx2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054403/bx2254Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (20971096) for financial support.

supplementary crystallographic information

Comment

Organotin complexes are attracting more and more attention because of their considerable structural diversity and interesting topologies (Murugavel et al. 2001). Herein, we report the crystal structure of the title compound. The title compound, which is shown in Fig.1 forms an infinite zigzag one-dimensional polymeric chain structure.The Sn atom is in a slightly distorted trigonal-bipyramidal coordination environment with two carboxylate O atoms in the axial sites and three methyl groups in equatorial site.The Sn—O, Sn—C bond lenghts and the O—Sn···O bond angles are close to the reported organotin compounds (Ma et al. 2006). The cyclohexene ring is in a distorted half-boat conformation, the ring-puckering parameters (Cremer & Pople, 1975) are q2 = 0.380 (1) Å , q3 = -0.314 (1) Å , Q = 0.492 (9) ° and [var phi]2 = 165.1 (2)°. There is an intramolecular C—H···O hydrogen bond (H3B—O2 2.60 , C3—O2 2.926 (10) Å, C3—H3B···O2 100°).

Experimental

The reaction was carried out under nitrogen atmosphere. 3-cyclohexene-1-carboxylic acid (1 mmol) and sodium ethoxide (1 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from ether to yield colorless blocks of the title compound (yield 86% m.p.448 K). Anal. Calcd (%) for C10H18O2Sn1 (Mr = 288.93): C, 41.57; H, 6.28; Found (%): C, 41.76; H, 6.01.

Refinement

All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C), for the others.

Figures

Fig. 1.
Part of the polymericstructure and the atom-numbering scheme of the title compound. Displacementellipsoids are shown at the 30% probability level and H atoms have been omitted for clarity.
Fig. 2.
Part of the structure of (I) showing the one-dimensional chain along the b axis[symmetry codes: (i) 1/2-x,-1/2+y, 1/2-z; (ii) 1/2-x,1/2+y,1/2-z].

Crystal data

[Sn(CH3)3(C7H9O2)]F(000) = 576
Mr = 288.93Dx = 1.533 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2901 reflections
a = 11.3022 (15) Åθ = 2.8–25.7°
b = 9.8469 (14) ŵ = 2.01 mm1
c = 12.1468 (18) ÅT = 298 K
β = 112.148 (2)°Block, colourless
V = 1252.1 (3) Å30.45 × 0.36 × 0.33 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer2193 independent reflections
Radiation source: fine-focus sealed tube1669 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.464, Tmax = 0.556k = −10→11
6095 measured reflectionsl = −14→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0436P)2 + 2.3141P] where P = (Fo2 + 2Fc2)/3
2193 reflections(Δ/σ)max = 0.001
118 parametersΔρmax = 1.53 e Å3
0 restraintsΔρmin = −0.49 e Å3

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

xyzUiso*/Ueq
Sn10.17568 (3)0.09824 (4)0.23917 (3)0.04584 (17)
O10.3014 (4)0.2882 (4)0.2205 (5)0.0699 (12)
O20.4496 (4)0.4411 (4)0.2415 (4)0.0652 (12)
C10.4091 (6)0.3183 (6)0.2231 (6)0.0574 (15)
C20.4961 (6)0.2138 (7)0.2052 (7)0.0694 (18)
H20.45290.12550.19150.083*
C30.5310 (8)0.2458 (9)0.1026 (8)0.101 (3)
H3A0.45390.24510.03130.121*
H3B0.56540.33730.11250.121*
C40.6246 (10)0.1532 (11)0.0847 (10)0.118 (3)
H40.62770.14370.00970.142*
C50.7028 (9)0.0848 (9)0.1741 (10)0.098 (3)
H50.76120.02750.16030.118*
C60.7047 (9)0.0922 (9)0.2906 (10)0.104 (3)
H6A0.79200.10770.34490.125*
H6B0.67810.00510.31060.125*
C70.6205 (7)0.2020 (9)0.3105 (8)0.091 (2)
H7A0.60320.18060.38090.109*
H7B0.66500.28830.32360.109*
C80.1852 (7)0.0177 (7)0.0817 (6)0.0684 (18)
H8A0.2669−0.02440.09940.103*
H8B0.17420.08960.02530.103*
H8C0.1189−0.04860.04890.103*
C90.0327 (6)0.2468 (6)0.2198 (7)0.072 (2)
H9A0.00320.23840.28400.109*
H9B−0.03750.23330.14560.109*
H9C0.06790.33580.22120.109*
C100.3183 (7)0.0735 (7)0.4101 (6)0.075 (2)
H10A0.39650.04550.40310.113*
H10B0.29170.00570.45280.113*
H10C0.33150.15810.45230.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0474 (3)0.0394 (2)0.0517 (3)0.00229 (17)0.01983 (19)0.00063 (18)
O10.065 (3)0.049 (2)0.105 (4)−0.003 (2)0.043 (3)−0.001 (3)
O20.063 (3)0.046 (2)0.102 (4)−0.0029 (19)0.048 (3)−0.007 (2)
C10.063 (4)0.046 (3)0.070 (4)0.004 (3)0.032 (3)0.003 (3)
C20.066 (4)0.053 (4)0.098 (5)0.005 (3)0.041 (4)−0.009 (4)
C30.114 (6)0.101 (6)0.110 (7)0.027 (5)0.068 (6)−0.007 (5)
C40.129 (8)0.132 (8)0.110 (8)0.048 (7)0.065 (7)−0.001 (7)
C50.090 (6)0.092 (6)0.123 (8)0.026 (5)0.054 (6)−0.011 (6)
C60.097 (6)0.092 (6)0.121 (8)0.033 (5)0.039 (6)0.008 (6)
C70.085 (5)0.087 (6)0.103 (6)0.021 (5)0.040 (5)0.005 (5)
C80.077 (4)0.073 (4)0.059 (4)−0.006 (4)0.030 (4)−0.006 (4)
C90.061 (4)0.049 (3)0.111 (6)0.012 (3)0.036 (4)0.016 (4)
C100.079 (5)0.080 (5)0.054 (4)0.002 (4)0.009 (4)0.006 (4)

Geometric parameters (Å, °)

Sn1—C102.108 (7)C5—C61.408 (14)
Sn1—C82.110 (6)C5—H50.9300
Sn1—C92.126 (6)C6—C71.519 (11)
Sn1—O2i2.169 (4)C6—H6A0.9700
Sn1—O12.411 (4)C6—H6B0.9700
O1—C11.241 (7)C7—H7A0.9700
O2—C11.282 (7)C7—H7B0.9700
O2—Sn1ii2.169 (4)C8—H8A0.9600
C1—C21.495 (8)C8—H8B0.9600
C2—C31.475 (10)C8—H8C0.9600
C2—C71.506 (10)C9—H9A0.9600
C2—H20.9800C9—H9B0.9600
C3—C41.474 (11)C9—H9C0.9600
C3—H3A0.9700C10—H10A0.9600
C3—H3B0.9700C10—H10B0.9600
C4—C51.300 (13)C10—H10C0.9600
C4—H40.9300
C10—Sn1—C8124.6 (3)C6—C5—H5118.0
C10—Sn1—C9117.1 (3)C5—C6—C7115.0 (8)
C8—Sn1—C9117.0 (3)C5—C6—H6A108.5
C10—Sn1—O2i95.7 (2)C7—C6—H6A108.5
C8—Sn1—O2i95.1 (2)C5—C6—H6B108.5
C9—Sn1—O2i90.2 (2)C7—C6—H6B108.5
C10—Sn1—O185.6 (2)H6A—C6—H6B107.5
C8—Sn1—O188.4 (2)C2—C7—C6111.1 (7)
C9—Sn1—O184.6 (2)C2—C7—H7A109.4
O2i—Sn1—O1174.62 (14)C6—C7—H7A109.4
C1—O1—Sn1142.2 (4)C2—C7—H7B109.4
C1—O2—Sn1ii119.1 (4)C6—C7—H7B109.4
O1—C1—O2120.8 (5)H7A—C7—H7B108.0
O1—C1—C2121.6 (6)Sn1—C8—H8A109.5
O2—C1—C2117.6 (5)Sn1—C8—H8B109.5
C3—C2—C1112.1 (6)H8A—C8—H8B109.5
C3—C2—C7105.8 (6)Sn1—C8—H8C109.5
C1—C2—C7112.6 (6)H8A—C8—H8C109.5
C3—C2—H2108.8H8B—C8—H8C109.5
C1—C2—H2108.8Sn1—C9—H9A109.5
C7—C2—H2108.8Sn1—C9—H9B109.5
C4—C3—C2115.3 (8)H9A—C9—H9B109.5
C4—C3—H3A108.4Sn1—C9—H9C109.5
C2—C3—H3A108.4H9A—C9—H9C109.5
C4—C3—H3B108.4H9B—C9—H9C109.5
C2—C3—H3B108.4Sn1—C10—H10A109.5
H3A—C3—H3B107.5Sn1—C10—H10B109.5
C5—C4—C3119.8 (9)H10A—C10—H10B109.5
C5—C4—H4120.1Sn1—C10—H10C109.5
C3—C4—H4120.1H10A—C10—H10C109.5
C4—C5—C6124.1 (8)H10B—C10—H10C109.5
C4—C5—H5118.0

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3B···O20.972.602.926 (10)100

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2254).

References

  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem.691, 1713–1721.
  • Murugavel, R., Baheti, K. & Anantharaman, G. (2001). Inorg. Chem.40, 6870–6878. [PubMed]
  • 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.

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