supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m719    [ doi:10.1107/S1600536809020340 ]

Dichloridobis(2-methylquinolin-8-olato-[kappa]2N,O)tin(IV)

K. M. Lo and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] 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.
Dichloridobis(2-methylquinolin-8-olato-κ2N,O)tin(IV) top
Crystal data top
[Sn(C10H8NO)2Cl2]Z = 2
Mr = 505.94F(000) = 500
Triclinic, P1Dx = 1.814 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		4189 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 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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
[Sn(C10H8NO)2Cl2]γ = 109.236 (1)°
Mr = 505.94V = 926.29 (2) Å3
Triclinic, P1Z = 2
a = 7.9651 (1) ÅMo Kα radiation
b = 9.6336 (1) ŵ = 1.69 mm−1
c = 12.8337 (2) ÅT = 133 K
α = 94.599 (1)°0.20 × 0.10 × 0.05 mm
β = 90.262 (1)°
Data collection top
Bruker SMART APEX
diffractometer		4189 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3905 reflections with I > 2σ(I)
Tmin = 0.729, Tmax = 0.920Rint = 0.015
7670 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.060Δρmax = 0.79 e Å−3
S = 1.03Δρmin = −0.34 e Å−3
4189 reflectionsAbsolute structure: ?
246 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

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

references
References top

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.

Westrip, S. P. (2009). publCIF. In preparation.