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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m719.
Published online 2009 June 6. doi:  10.1107/S1600536809020340
PMCID: PMC2969261

Dichloridobis(2-methyl­quinolin-8-olato-κ2 N,O)tin(IV)

Abstract

The bis-chelated Sn atom in the title compound, [Sn(C10H8NO)2Cl2], exists in a distorted cis-Cl2,cis-N2,trans-O2 octa­hedral environment.

Related literature

For the crystal structure of dichloridobis(8-oxidoquinoline), see: Archer et al. (1987 [triangle]).

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Object name is e-65-0m719-scheme1.jpg

Experimental

Crystal data

  • [Sn(C10H8NO)2Cl2]
  • M r = 505.94
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m719-efi1.jpg
  • a = 7.9651 (1) Å
  • b = 9.6336 (1) Å
  • c = 12.8337 (2) Å
  • α = 94.599 (1)°
  • β = 90.262 (1)°
  • γ = 109.236 (1)°
  • V = 926.29 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.69 mm−1
  • T = 133 K
  • 0.20 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.729, T max = 0.920
  • 7670 measured reflections
  • 4189 independent reflections
  • 3905 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.060
  • S = 1.03
  • 4189 reflections
  • 246 parameters
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020340/tk2467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020340/tk2467Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Experimental

Di(p-chlorobenzyl)tin dichloride (0.44 g, 1 mmol) and 8-hydroxyquinaldine (0.16 g, 1 mmol) were dissolved in chloroform (100 ml) and the solution was heated for 1 hour. Slow evaporation of the filtrate gave yellow crystals. The organic groups at tin were probabaly cleaved by the heterocycle in the reaction.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of SnCl2(C10H8NO)2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C10H8NO)2Cl2]Z = 2
Mr = 505.94F(000) = 500
Triclinic, P1Dx = 1.814 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9651 (1) ÅCell parameters from 9941 reflections
b = 9.6336 (1) Åθ = 2.4–28.2°
c = 12.8337 (2) ŵ = 1.69 mm1
α = 94.599 (1)°T = 133 K
β = 90.262 (1)°Prism, pale yellow
γ = 109.236 (1)°0.20 × 0.10 × 0.05 mm
V = 926.29 (2) Å3

Data collection

Bruker SMART APEX diffractometer4189 independent reflections
Radiation source: fine-focus sealed tube3905 reflections with I > 2σ(I)
graphiteRint = 0.015
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.729, Tmax = 0.920k = −12→12
7670 measured reflectionsl = −16→16

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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0346P)2 + 0.4719P] where P = (Fo2 + 2Fc2)/3
4189 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = −0.34 e Å3

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

xyzUiso*/Ueq
Sn10.276677 (18)0.727420 (15)0.279378 (11)0.01746 (6)
Cl10.03285 (7)0.77602 (6)0.20001 (4)0.02382 (12)
Cl20.24196 (8)0.82902 (6)0.44903 (4)0.02532 (12)
N10.4783 (2)0.6315 (2)0.34153 (14)0.0183 (4)
N20.3536 (2)0.6733 (2)0.11290 (15)0.0200 (4)
O10.1236 (2)0.51786 (17)0.29867 (13)0.0221 (3)
O20.4661 (2)0.91742 (17)0.25039 (13)0.0240 (3)
C10.7366 (3)0.8568 (3)0.37939 (19)0.0250 (5)
H1A0.65220.90470.40570.038*
H1B0.77460.88850.31010.038*
H1C0.84060.88470.42750.038*
C20.6490 (3)0.6930 (3)0.37157 (17)0.0200 (4)
C30.7488 (3)0.6025 (3)0.39744 (19)0.0247 (5)
H30.87090.64700.41770.030*
C40.6739 (3)0.4537 (3)0.39396 (19)0.0260 (5)
H40.74440.39480.40930.031*
C50.4912 (3)0.3865 (3)0.36755 (17)0.0225 (5)
C60.3986 (4)0.2331 (3)0.36603 (19)0.0283 (5)
H60.46030.16730.38070.034*
C70.2184 (4)0.1802 (3)0.3431 (2)0.0311 (6)
H70.15670.07720.34190.037*
C80.1239 (3)0.2753 (3)0.32133 (19)0.0272 (5)
H8−0.00090.23600.30730.033*
C90.2103 (3)0.4248 (2)0.32009 (17)0.0208 (4)
C100.3970 (3)0.4819 (2)0.34239 (17)0.0192 (4)
C110.1273 (3)0.4305 (3)0.0696 (2)0.0285 (5)
H11A0.04240.46580.10940.043*
H11B0.17060.36840.11200.043*
H11C0.06850.37290.00530.043*
C120.2808 (3)0.5597 (3)0.04230 (18)0.0228 (5)
C130.3471 (4)0.5605 (3)−0.0607 (2)0.0302 (5)
H130.29150.4812−0.11170.036*
C140.4896 (4)0.6746 (3)−0.0858 (2)0.0313 (6)
H140.53520.6729−0.15400.038*
C150.5713 (3)0.7955 (3)−0.01254 (19)0.0269 (5)
C160.7162 (3)0.9198 (3)−0.0338 (2)0.0348 (6)
H160.77120.9228−0.09950.042*
C170.7769 (4)1.0357 (3)0.0405 (2)0.0374 (7)
H170.87721.11770.02650.045*
C180.6947 (3)1.0370 (3)0.1376 (2)0.0311 (6)
H180.73781.12040.18710.037*
C190.5515 (3)0.9171 (3)0.16080 (19)0.0238 (5)
C200.4932 (3)0.7921 (3)0.08655 (18)0.0212 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01921 (8)0.01482 (8)0.01839 (9)0.00572 (6)0.00134 (6)0.00120 (6)
Cl10.0241 (3)0.0261 (3)0.0234 (3)0.0112 (2)0.0001 (2)0.0025 (2)
Cl20.0310 (3)0.0255 (3)0.0213 (3)0.0128 (2)0.0006 (2)−0.0018 (2)
N10.0213 (9)0.0184 (9)0.0158 (9)0.0071 (7)0.0017 (7)0.0015 (7)
N20.0210 (9)0.0214 (9)0.0193 (9)0.0091 (8)0.0002 (7)0.0034 (8)
O10.0194 (7)0.0183 (8)0.0275 (9)0.0041 (6)0.0000 (6)0.0045 (7)
O20.0267 (8)0.0169 (8)0.0258 (9)0.0037 (6)0.0018 (7)0.0016 (7)
C10.0209 (10)0.0239 (12)0.0271 (12)0.0038 (9)−0.0021 (9)−0.0004 (10)
C20.0215 (10)0.0230 (11)0.0152 (10)0.0067 (9)0.0024 (8)0.0019 (9)
C30.0206 (10)0.0332 (13)0.0220 (12)0.0110 (10)0.0017 (9)0.0042 (10)
C40.0322 (12)0.0309 (13)0.0214 (12)0.0187 (11)0.0019 (9)0.0048 (10)
C50.0310 (12)0.0241 (11)0.0150 (11)0.0124 (10)0.0016 (9)0.0026 (9)
C60.0436 (14)0.0219 (12)0.0236 (12)0.0161 (11)−0.0004 (10)0.0035 (10)
C70.0463 (15)0.0151 (11)0.0286 (13)0.0058 (10)−0.0042 (11)0.0019 (10)
C80.0304 (12)0.0218 (12)0.0260 (13)0.0036 (10)−0.0031 (10)0.0040 (10)
C90.0265 (11)0.0172 (10)0.0182 (11)0.0064 (9)0.0004 (9)0.0020 (9)
C100.0262 (11)0.0173 (10)0.0144 (10)0.0080 (9)0.0014 (8)0.0005 (8)
C110.0342 (13)0.0235 (12)0.0256 (13)0.0074 (10)−0.0039 (10)−0.0018 (10)
C120.0259 (11)0.0239 (11)0.0216 (12)0.0123 (9)−0.0006 (9)0.0010 (9)
C130.0362 (13)0.0364 (14)0.0233 (12)0.0198 (12)−0.0007 (10)−0.0004 (11)
C140.0365 (13)0.0439 (15)0.0199 (12)0.0213 (12)0.0050 (10)0.0065 (11)
C150.0265 (12)0.0349 (14)0.0241 (12)0.0150 (10)0.0038 (10)0.0088 (11)
C160.0294 (13)0.0446 (16)0.0329 (15)0.0120 (12)0.0106 (11)0.0184 (13)
C170.0258 (12)0.0406 (16)0.0446 (17)0.0049 (11)0.0063 (11)0.0231 (14)
C180.0285 (12)0.0271 (13)0.0349 (14)0.0035 (10)−0.0028 (11)0.0110 (11)
C190.0219 (10)0.0247 (12)0.0257 (12)0.0076 (9)0.0000 (9)0.0090 (10)
C200.0194 (10)0.0242 (11)0.0223 (12)0.0091 (9)0.0005 (8)0.0073 (9)

Geometric parameters (Å, °)

Sn1—O22.0149 (16)C6—H60.9500
Sn1—O12.0211 (16)C7—C81.406 (3)
Sn1—N12.2703 (18)C7—H70.9500
Sn1—N22.2925 (19)C8—C91.379 (3)
Sn1—Cl22.3700 (6)C8—H80.9500
Sn1—Cl12.3846 (5)C9—C101.424 (3)
N1—C21.332 (3)C11—C121.495 (3)
N1—C101.373 (3)C11—H11A0.9800
N2—C121.332 (3)C11—H11B0.9800
N2—C201.374 (3)C11—H11C0.9800
O1—C91.342 (3)C12—C131.425 (3)
O2—C191.339 (3)C13—C141.356 (4)
C1—C21.496 (3)C13—H130.9500
C1—H1A0.9800C14—C151.408 (4)
C1—H1B0.9800C14—H140.9500
C1—H1C0.9800C15—C161.409 (4)
C2—C31.415 (3)C15—C201.416 (3)
C3—C41.356 (4)C16—C171.364 (4)
C3—H30.9500C16—H160.9500
C4—C51.411 (3)C17—C181.411 (4)
C4—H40.9500C17—H170.9500
C5—C61.416 (3)C18—C191.384 (3)
C5—C101.418 (3)C18—H180.9500
C6—C71.377 (4)C19—C201.420 (3)
O2—Sn1—O1168.37 (6)C6—C7—H7119.3
O2—Sn1—N192.76 (7)C8—C7—H7119.3
O1—Sn1—N178.04 (6)C9—C8—C7120.7 (2)
O2—Sn1—N277.90 (7)C9—C8—H8119.7
O1—Sn1—N294.63 (7)C7—C8—H8119.7
N1—Sn1—N288.77 (6)O1—C9—C8121.9 (2)
O2—Sn1—Cl290.74 (5)O1—C9—C10119.2 (2)
O1—Sn1—Cl296.53 (5)C8—C9—C10118.9 (2)
N1—Sn1—Cl291.39 (5)N1—C10—C5122.3 (2)
N2—Sn1—Cl2168.62 (5)N1—C10—C9117.31 (19)
O2—Sn1—Cl197.04 (5)C5—C10—C9120.4 (2)
O1—Sn1—Cl191.31 (5)C12—C11—H11A109.5
N1—Sn1—Cl1167.95 (5)C12—C11—H11B109.5
N2—Sn1—Cl186.47 (5)H11A—C11—H11B109.5
Cl2—Sn1—Cl195.46 (2)C12—C11—H11C109.5
C2—N1—C10119.95 (19)H11A—C11—H11C109.5
C2—N1—Sn1132.09 (15)H11B—C11—H11C109.5
C10—N1—Sn1107.93 (14)N2—C12—C13120.3 (2)
C12—N2—C20120.0 (2)N2—C12—C11120.5 (2)
C12—N2—Sn1132.03 (15)C13—C12—C11119.2 (2)
C20—N2—Sn1107.76 (15)C14—C13—C12120.0 (3)
C9—O1—Sn1116.18 (13)C14—C13—H13120.0
C19—O2—Sn1116.82 (15)C12—C13—H13120.0
C2—C1—H1A109.5C13—C14—C15121.2 (2)
C2—C1—H1B109.5C13—C14—H14119.4
H1A—C1—H1B109.5C15—C14—H14119.4
C2—C1—H1C109.5C16—C15—C20119.3 (2)
H1A—C1—H1C109.5C16—C15—C14124.4 (2)
H1B—C1—H1C109.5C20—C15—C14116.2 (2)
N1—C2—C3119.7 (2)C17—C16—C15119.5 (2)
N1—C2—C1120.9 (2)C17—C16—H16120.2
C3—C2—C1119.4 (2)C15—C16—H16120.2
C4—C3—C2121.4 (2)C16—C17—C18121.7 (2)
C4—C3—H3119.3C16—C17—H17119.1
C2—C3—H3119.3C18—C17—H17119.1
C3—C4—C5119.9 (2)C19—C18—C17120.2 (3)
C3—C4—H4120.0C19—C18—H18119.9
C5—C4—H4120.0C17—C18—H18119.9
C4—C5—C6124.3 (2)O2—C19—C18121.6 (2)
C4—C5—C10116.5 (2)O2—C19—C20119.7 (2)
C6—C5—C10119.2 (2)C18—C19—C20118.7 (2)
C7—C6—C5119.4 (2)N2—C20—C15122.2 (2)
C7—C6—H6120.3N2—C20—C19117.4 (2)
C5—C6—H6120.3C15—C20—C19120.3 (2)
C6—C7—C8121.4 (2)
O2—Sn1—N1—C214.7 (2)Sn1—O1—C9—C108.9 (3)
O1—Sn1—N1—C2−172.5 (2)C7—C8—C9—O1179.4 (2)
N2—Sn1—N1—C292.5 (2)C7—C8—C9—C10−0.7 (4)
Cl2—Sn1—N1—C2−76.09 (19)C2—N1—C10—C5−4.4 (3)
Cl1—Sn1—N1—C2159.21 (17)Sn1—N1—C10—C5173.84 (17)
O2—Sn1—N1—C10−163.29 (14)C2—N1—C10—C9173.6 (2)
O1—Sn1—N1—C109.52 (14)Sn1—N1—C10—C9−8.2 (2)
N2—Sn1—N1—C10−85.47 (14)C4—C5—C10—N11.2 (3)
Cl2—Sn1—N1—C10105.91 (13)C6—C5—C10—N1−179.5 (2)
Cl1—Sn1—N1—C10−18.8 (3)C4—C5—C10—C9−176.7 (2)
O2—Sn1—N2—C12−170.0 (2)C6—C5—C10—C92.6 (3)
O1—Sn1—N2—C1219.05 (19)O1—C9—C10—N10.5 (3)
N1—Sn1—N2—C1296.95 (19)C8—C9—C10—N1−179.3 (2)
Cl2—Sn1—N2—C12−172.14 (17)O1—C9—C10—C5178.6 (2)
Cl1—Sn1—N2—C12−71.98 (19)C8—C9—C10—C5−1.3 (3)
O2—Sn1—N2—C204.49 (13)C20—N2—C12—C130.0 (3)
O1—Sn1—N2—C20−166.49 (13)Sn1—N2—C12—C13173.93 (16)
N1—Sn1—N2—C20−88.60 (14)C20—N2—C12—C11−179.3 (2)
Cl2—Sn1—N2—C202.3 (3)Sn1—N2—C12—C11−5.4 (3)
Cl1—Sn1—N2—C20102.47 (13)N2—C12—C13—C142.7 (3)
O2—Sn1—O1—C928.5 (4)C11—C12—C13—C14−178.0 (2)
N1—Sn1—O1—C9−9.83 (15)C12—C13—C14—C15−1.8 (4)
N2—Sn1—O1—C977.92 (16)C13—C14—C15—C16−178.1 (2)
Cl2—Sn1—O1—C9−99.87 (15)C13—C14—C15—C20−1.6 (3)
Cl1—Sn1—O1—C9164.49 (15)C20—C15—C16—C17−1.1 (4)
O1—Sn1—O2—C1944.7 (4)C14—C15—C16—C17175.2 (2)
N1—Sn1—O2—C1982.07 (16)C15—C16—C17—C18−2.1 (4)
N2—Sn1—O2—C19−6.07 (15)C16—C17—C18—C191.8 (4)
Cl2—Sn1—O2—C19173.50 (15)Sn1—O2—C19—C18−173.95 (17)
Cl1—Sn1—O2—C19−90.91 (15)Sn1—O2—C19—C207.0 (3)
C10—N1—C2—C34.3 (3)C17—C18—C19—O2−177.2 (2)
Sn1—N1—C2—C3−173.52 (15)C17—C18—C19—C201.9 (3)
C10—N1—C2—C1−175.1 (2)C12—N2—C20—C15−3.7 (3)
Sn1—N1—C2—C17.1 (3)Sn1—N2—C20—C15−178.95 (17)
N1—C2—C3—C4−1.0 (3)C12—N2—C20—C19172.74 (19)
C1—C2—C3—C4178.4 (2)Sn1—N2—C20—C19−2.5 (2)
C2—C3—C4—C5−2.2 (4)C16—C15—C20—N2−178.9 (2)
C3—C4—C5—C6−177.2 (2)C14—C15—C20—N24.4 (3)
C3—C4—C5—C102.1 (3)C16—C15—C20—C194.7 (3)
C4—C5—C6—C7177.4 (2)C14—C15—C20—C19−171.9 (2)
C10—C5—C6—C7−1.8 (3)O2—C19—C20—N2−2.5 (3)
C5—C6—C7—C8−0.2 (4)C18—C19—C20—N2178.4 (2)
C6—C7—C8—C91.5 (4)O2—C19—C20—C15174.04 (19)
Sn1—O1—C9—C8−171.26 (18)C18—C19—C20—C15−5.1 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2467).

References

  • Archer, S. J., Koch, K. R. & Schmidt, S. (1987). Inorg. Chim. Acta, 126, 209–218.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). 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]
  • Westrip, S. P. (2009). publCIF In preparation.

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