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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m947.
Published online 2010 July 17. doi:  10.1107/S1600536810027595
PMCID: PMC3007314

Chloridomethyl­phen­yl(quinoline-2-carboxyl­ato-κ2 N,O)tin(IV)

Abstract

The Sn atom in the title compound, [Sn(CH3)(C6H5)(C10H6NO2)Cl], shows a distorted C2SnNOCl trigonal-bipyramidal coordination; the apical sites are occupied by the N and Cl atoms.

Related literature

For chloridodimeth­yl(quinoline-2-carboxyl­ato)tin(IV), see: Wang et al. (2007 [triangle]).

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Object name is e-66-0m947-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)(C6H5)(C10H6NO2)Cl]
  • M r = 418.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m947-efi1.jpg
  • a = 10.6942 (5) Å
  • b = 13.1463 (6) Å
  • c = 11.2733 (5) Å
  • β = 93.689 (1)°
  • V = 1581.6 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.79 mm−1
  • T = 100 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.616, T max = 0.841
  • 14187 measured reflections
  • 3613 independent reflections
  • 3433 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.096
  • S = 1.40
  • 3613 reflections
  • 201 parameters
  • H-atom parameters constrained
  • Δρmax = 1.74 e Å−3
  • Δρmin = −0.94 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027595/bt5296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027595/bt5296Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The tin atom in chlorodimethyl(quinoline-2-carboxylate)tin shows cis-C2SnNOCl trigonal bipyramidal coordination, with the C2Sn skeleton being bent at 131.8 (2) ° (Wang et al., 2007). Replacing one of the methyl groups by a bulkier phenyl group in the title analog (Scheme I, Fig. 1) leads to only a marginal opening of the angle 138.6 (1) °; the trans angle is also marginally increased.

Experimental

Sodium quinoline-2-carboxylate was synthesized by reacting sodium hydroxide and quinoline-2-carboxylic acid in toluene in a Dean-Start apparatus. The compound (0.20 g, 1 mmol) was then stirred with methylphenyltin dichloride (0.35 g, 1 mmol) in toluene; no heat was applied. The precipitate that formed was recrystallized from methanol.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

The final difference Fourier map had a peak (1.741eÅ-3) at 0.78 Å from Sn1.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl(CH3)(C6H5)(C10H6NO2) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(CH3)(C6H5)(C10H6NO2)Cl]F(000) = 824
Mr = 418.43Dx = 1.757 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9943 reflections
a = 10.6942 (5) Åθ = 2.4–28.3°
b = 13.1463 (6) ŵ = 1.79 mm1
c = 11.2733 (5) ÅT = 100 K
β = 93.689 (1)°Prism, colorless
V = 1581.6 (1) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3613 independent reflections
Radiation source: fine-focus sealed tube3433 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.616, Tmax = 0.841k = −17→17
14187 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.096w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1663P] where P = (Fo2 + 2Fc2)/3
S = 1.40(Δ/σ)max = 0.001
3613 reflectionsΔρmax = 1.74 e Å3
201 parametersΔρmin = −0.94 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0280 (15)

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

xyzUiso*/Ueq
Sn10.813061 (14)0.776948 (11)0.733408 (14)0.01396 (11)
Cl11.02998 (6)0.75394 (6)0.68330 (7)0.02452 (16)
O10.77940 (15)0.62981 (12)0.67664 (15)0.0176 (3)
O20.64876 (17)0.49885 (13)0.64587 (16)0.0217 (4)
C10.8465 (3)0.77556 (17)0.9205 (3)0.0226 (6)
H1A0.77420.80460.95750.034*
H1B0.92130.81600.94280.034*
H1C0.85960.70540.94790.034*
C20.7644 (2)0.88296 (16)0.59620 (19)0.0139 (4)
C30.6502 (2)0.87698 (17)0.52921 (19)0.0161 (4)
H30.59310.82360.54350.019*
C40.6195 (2)0.94912 (19)0.4413 (2)0.0193 (5)
H40.54270.94380.39450.023*
C50.7010 (2)1.02855 (18)0.4224 (2)0.0203 (5)
H50.67851.07910.36470.024*
C60.8157 (2)1.03451 (17)0.4877 (2)0.0197 (5)
H60.87191.08870.47420.024*
C70.8479 (2)0.96066 (17)0.5731 (2)0.0167 (4)
H70.92740.96340.61580.020*
C80.6698 (2)0.58635 (18)0.6779 (2)0.0163 (4)
C90.5661 (2)0.65049 (17)0.72434 (19)0.0146 (4)
C100.4453 (2)0.61082 (18)0.7341 (2)0.0178 (4)
H100.42550.54350.70890.021*
C110.3567 (2)0.67171 (19)0.7810 (2)0.0187 (5)
H110.27470.64620.78980.022*
C120.3874 (3)0.77218 (16)0.8162 (2)0.0158 (5)
C130.3008 (2)0.83899 (19)0.8662 (2)0.0193 (5)
H130.21940.81530.88130.023*
C140.3339 (2)0.9378 (2)0.8929 (2)0.0207 (5)
H140.27590.98190.92710.025*
C150.4546 (2)0.97368 (18)0.86940 (19)0.0186 (5)
H150.47541.04290.88450.022*
C160.5418 (2)0.91036 (18)0.82531 (19)0.0172 (4)
H160.62340.93510.81260.021*
C170.5105 (2)0.80846 (18)0.79870 (19)0.0140 (4)
N10.5977 (2)0.74461 (18)0.75477 (18)0.0139 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01151 (15)0.01373 (15)0.01635 (15)−0.00098 (4)−0.00142 (8)0.00397 (4)
Cl10.0122 (3)0.0219 (3)0.0395 (4)0.0004 (3)0.0017 (2)0.0078 (3)
O10.0146 (8)0.0141 (8)0.0244 (9)−0.0003 (6)0.0028 (6)−0.0009 (6)
O20.0208 (9)0.0156 (8)0.0286 (9)−0.0014 (7)0.0008 (7)−0.0046 (7)
C10.0274 (15)0.0217 (13)0.0179 (13)−0.0011 (9)−0.0052 (11)0.0035 (8)
C20.0152 (10)0.0134 (10)0.0133 (9)0.0019 (8)0.0027 (8)0.0011 (8)
C30.0148 (11)0.0176 (11)0.0162 (10)0.0009 (8)0.0020 (8)−0.0006 (8)
C40.0192 (11)0.0236 (12)0.0152 (10)0.0072 (9)0.0004 (8)−0.0009 (9)
C50.0302 (13)0.0177 (12)0.0134 (10)0.0090 (10)0.0054 (9)0.0024 (8)
C60.0268 (12)0.0135 (10)0.0198 (11)0.0006 (9)0.0088 (9)0.0020 (8)
C70.0179 (11)0.0145 (10)0.0178 (10)−0.0005 (8)0.0021 (8)−0.0007 (8)
C80.0174 (11)0.0164 (11)0.0151 (10)−0.0006 (8)0.0011 (8)0.0020 (8)
C90.0139 (11)0.0154 (11)0.0142 (10)−0.0005 (8)−0.0007 (8)0.0022 (8)
C100.0166 (11)0.0143 (10)0.0223 (11)−0.0033 (8)−0.0002 (9)0.0030 (8)
C110.0142 (11)0.0196 (12)0.0223 (11)−0.0028 (9)0.0013 (9)0.0067 (9)
C120.0133 (12)0.0207 (13)0.0135 (11)0.0010 (8)0.0012 (9)0.0060 (7)
C130.0170 (11)0.0253 (12)0.0157 (10)0.0016 (9)0.0022 (8)0.0041 (8)
C140.0218 (12)0.0257 (13)0.0146 (10)0.0059 (10)0.0011 (9)0.0002 (9)
C150.0245 (12)0.0174 (11)0.0135 (10)0.0005 (9)−0.0023 (9)−0.0012 (8)
C160.0193 (11)0.0176 (11)0.0147 (10)−0.0016 (8)−0.0002 (8)0.0017 (8)
C170.0144 (11)0.0163 (11)0.0113 (9)−0.0004 (9)0.0001 (8)0.0029 (8)
N10.0136 (10)0.0142 (9)0.0139 (9)−0.0009 (8)0.0001 (7)0.0025 (8)

Geometric parameters (Å, °)

Sn1—C12.117 (3)C7—H70.9500
Sn1—C22.122 (2)C8—C91.513 (3)
Sn1—N12.369 (2)C9—N11.322 (3)
Sn1—O12.062 (2)C9—C101.404 (3)
Sn1—Cl12.4414 (7)C10—C111.373 (3)
O1—C81.305 (3)C10—H100.9500
O2—C81.222 (3)C11—C121.412 (4)
C1—H1A0.9800C11—H110.9500
C1—H1B0.9800C12—C131.420 (3)
C1—H1C0.9800C12—C171.426 (3)
C2—C71.392 (3)C13—C141.375 (4)
C2—C31.397 (3)C13—H130.9500
C3—C41.395 (3)C14—C151.415 (4)
C3—H30.9500C14—H140.9500
C4—C51.385 (4)C15—C161.367 (3)
C4—H40.9500C15—H150.9500
C5—C61.392 (4)C16—C171.408 (3)
C5—H50.9500C16—H160.9500
C6—C71.394 (3)C17—N11.371 (3)
C6—H60.9500
O1—Sn1—C1108.43 (8)C6—C7—H7119.8
O1—Sn1—C2111.11 (7)O2—C8—O1123.9 (2)
C1—Sn1—C2138.58 (9)O2—C8—C9120.1 (2)
O1—Sn1—N173.25 (7)O1—C8—C9116.0 (2)
C1—Sn1—N190.02 (10)N1—C9—C10123.3 (2)
C2—Sn1—N189.86 (8)N1—C9—C8115.5 (2)
O1—Sn1—Cl187.79 (5)C10—C9—C8121.2 (2)
C1—Sn1—Cl197.31 (9)C11—C10—C9118.4 (2)
C2—Sn1—Cl196.02 (6)C11—C10—H10120.8
N1—Sn1—Cl1161.00 (7)C9—C10—H10120.8
C8—O1—Sn1123.13 (14)C10—C11—C12120.0 (2)
Sn1—C1—H1A109.5C10—C11—H11120.0
Sn1—C1—H1B109.5C12—C11—H11120.0
H1A—C1—H1B109.5C11—C12—C13123.0 (2)
Sn1—C1—H1C109.5C11—C12—C17118.3 (2)
H1A—C1—H1C109.5C13—C12—C17118.7 (2)
H1B—C1—H1C109.5C14—C13—C12120.4 (2)
C7—C2—C3119.3 (2)C14—C13—H13119.8
C7—C2—Sn1119.21 (16)C12—C13—H13119.8
C3—C2—Sn1121.48 (16)C13—C14—C15120.0 (2)
C4—C3—C2120.2 (2)C13—C14—H14120.0
C4—C3—H3119.9C15—C14—H14120.0
C2—C3—H3119.9C16—C15—C14121.1 (2)
C5—C4—C3120.0 (2)C16—C15—H15119.4
C5—C4—H4120.0C14—C15—H15119.4
C3—C4—H4120.0C15—C16—C17119.9 (2)
C4—C5—C6120.2 (2)C15—C16—H16120.1
C4—C5—H5119.9C17—C16—H16120.1
C6—C5—H5119.9N1—C17—C16120.1 (2)
C5—C6—C7119.7 (2)N1—C17—C12120.1 (2)
C5—C6—H6120.1C16—C17—C12119.8 (2)
C7—C6—H6120.1C9—N1—C17119.9 (2)
C2—C7—C6120.5 (2)C9—N1—Sn1112.07 (16)
C2—C7—H7119.8C17—N1—Sn1127.97 (17)
C1—Sn1—O1—C883.29 (19)C10—C11—C12—C13−179.5 (2)
C2—Sn1—O1—C8−84.14 (18)C10—C11—C12—C171.6 (4)
N1—Sn1—O1—C8−0.97 (16)C11—C12—C13—C14−176.5 (2)
Cl1—Sn1—O1—C8−179.74 (16)C17—C12—C13—C142.4 (3)
O1—Sn1—C2—C7−133.04 (16)C12—C13—C14—C150.7 (3)
C1—Sn1—C2—C765.2 (2)C13—C14—C15—C16−3.0 (3)
N1—Sn1—C2—C7155.02 (17)C14—C15—C16—C172.2 (3)
Cl1—Sn1—C2—C7−43.08 (17)C15—C16—C17—N1−179.8 (2)
O1—Sn1—C2—C347.46 (19)C15—C16—C17—C121.0 (3)
C1—Sn1—C2—C3−114.4 (2)C11—C12—C17—N1−3.5 (3)
N1—Sn1—C2—C3−24.49 (18)C13—C12—C17—N1177.5 (2)
Cl1—Sn1—C2—C3137.41 (17)C11—C12—C17—C16175.8 (2)
C7—C2—C3—C4−1.0 (3)C13—C12—C17—C16−3.2 (3)
Sn1—C2—C3—C4178.55 (16)C10—C9—N1—C170.2 (3)
C2—C3—C4—C5−1.7 (3)C8—C9—N1—C17−179.51 (19)
C3—C4—C5—C62.5 (3)C10—C9—N1—Sn1176.98 (17)
C4—C5—C6—C7−0.5 (3)C8—C9—N1—Sn1−2.7 (2)
C3—C2—C7—C62.9 (3)C16—C17—N1—C9−176.6 (2)
Sn1—C2—C7—C6−176.62 (17)C12—C17—N1—C92.6 (3)
C5—C6—C7—C2−2.2 (3)C16—C17—N1—Sn17.2 (3)
Sn1—O1—C8—O2−179.09 (17)C12—C17—N1—Sn1−173.62 (16)
Sn1—O1—C8—C9−0.1 (3)O1—Sn1—N1—C92.05 (15)
O2—C8—C9—N1−178.9 (2)C1—Sn1—N1—C9−107.22 (17)
O1—C8—C9—N12.1 (3)C2—Sn1—N1—C9114.19 (16)
O2—C8—C9—C101.4 (3)Cl1—Sn1—N1—C95.8 (3)
O1—C8—C9—C10−177.6 (2)O1—Sn1—N1—C17178.5 (2)
N1—C9—C10—C11−2.1 (3)C1—Sn1—N1—C1769.2 (2)
C8—C9—C10—C11177.6 (2)C2—Sn1—N1—C17−69.4 (2)
C9—C10—C11—C121.1 (4)Cl1—Sn1—N1—C17−177.71 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5296).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, H., Yin, H. & Wang, D. (2007). Acta Cryst. E63, m3059.
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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