supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

hb2644 scheme

Acta Cryst. (2007). E63, m2994    [ doi:10.1107/S1600536807056851 ]

Methanoltriphenyl(quinoline-2-carboxylato)tin(IV)

H. Wang, H. Yin and Y. Sun

Abstract top

The Sn atom in the title compound, [Sn(C6H5)3(C10H6NO2)(CH4O)], adopts a distorted SnO2C3 trigonal-bipyramidal geometry. The O atom of the carboxylate group occupies one of the axial sites and the O atom of the methanol molecule occupies the other. In the crystal structure, a bifurcated O-H...(O,N) hydrogen bond links adjacent molecules.

Comment top

Organotin esters of carboxylic acids are widely used as biocides, fungicides and homogeneous catalysts. Studies on organotin complexes containing carboxylate ligands with an additional donor atom (e.g. N, O or S) that is available for coordinating to the Sn atom have revealed that new structural types may lead to different activities. We have therefore synthesized the title compound, (I), and present its crystal structure here (Fig. 1).

The Sn in (I) atom assumes a trigonal-bipyramidal coordination geometry, formed by three phenyl groups, a monodentate carboxylate group and a coordinated methanol molecule (Table 1). The Sn—O distances in (I) are are close to those in related structures (Ma et al., 2006).

In the crystal of (I), the methanol O—H group makes a bifurcated O—H···(O,N) hydrogen bond (Table 2) to the carboxylate O atom and quinoline N atom in an adjacent molecule (Fig. 2).

Related literature top

For related structures, see: Ma et al. (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1) to yield colourless blocks of (I) (yield 83%; m.p. 446 K). Analysis calculated (%) for C29H25NO3Sn: C 62.85; H 4.55; N 2.53. Found: C 62.79; H 4.63; N 2.62%.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2xUeq(C,O) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The unit cell of (I). H atoms have been omitted for clarity. Hydrogen bonds are shown as dashed lines joining the donor and acceptor atoms.
Methanoltriphenyl(quinoline-2-carboxylato)tin(IV) top
Crystal data top
[Sn(C6H5)3(C10H6NO2)(CH4O)]F000 = 1120
Mr = 554.19Dx = 1.424 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5687 reflections
a = 11.1774 (11) Åθ = 2.3–26.9º
b = 14.3964 (12) ŵ = 1.02 mm−1
c = 16.098 (2) ÅT = 298 (2) K
β = 93.572 (2)ºBlock, colourless
V = 2585.3 (5) Å30.54 × 0.46 × 0.45 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer		4551 independent reflections
Radiation source: fine-focus sealed tube3424 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→13
Tmin = 0.610, Tmax = 0.657k = −17→14
12574 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.0547P)2 + 0.777P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
4551 reflectionsΔρmax = 0.90 e Å−3
307 parametersΔρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Sn(C6H5)3(C10H6NO2)(CH4O)]V = 2585.3 (5) Å3
Mr = 554.19Z = 4
Monoclinic, P21/nMo Kα
a = 11.1774 (11) ŵ = 1.02 mm−1
b = 14.3964 (12) ÅT = 298 (2) K
c = 16.098 (2) Å0.54 × 0.46 × 0.45 mm
β = 93.572 (2)º
Data collection top
Siemens SMART CCD
diffractometer		4551 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3424 reflections with I > 2σ(I)
Tmin = 0.610, Tmax = 0.657Rint = 0.040
12574 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029307 parameters
wR(F2) = 0.099H-atom parameters constrained
S = 1.00Δρmax = 0.90 e Å−3
4551 reflectionsΔρmin = −0.47 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.62676 (2)0.142033 (17)0.775590 (15)0.03955 (11)
N10.7000 (3)0.4632 (2)0.94373 (18)0.0415 (7)
O10.6090 (2)0.24000 (17)0.87443 (16)0.0510 (7)
O20.6980 (3)0.35405 (18)0.80596 (17)0.0559 (8)
O30.6358 (2)0.01729 (19)0.67387 (16)0.0503 (7)
H30.6984−0.00160.65590.075*
C10.6512 (3)0.3235 (3)0.8669 (2)0.0431 (9)
C20.6403 (3)0.3839 (3)0.9437 (2)0.0403 (8)
C30.5728 (4)0.3546 (3)1.0098 (2)0.0493 (10)
H3A0.53180.29841.00700.059*
C40.5685 (4)0.4104 (3)1.0787 (2)0.0546 (11)
H40.52370.39251.12270.066*
C50.6322 (4)0.4953 (3)1.0825 (2)0.0504 (10)
C60.6972 (3)0.5194 (3)1.0128 (2)0.0425 (9)
C70.7603 (4)0.6051 (3)1.0128 (3)0.0577 (11)
H70.80370.62150.96760.069*
C80.7567 (5)0.6632 (4)1.0797 (3)0.0735 (14)
H80.79760.71941.07950.088*
C90.6926 (5)0.6395 (4)1.1484 (3)0.0734 (14)
H90.69110.68041.19310.088*
C100.6328 (4)0.5583 (3)1.1510 (3)0.0657 (13)
H100.59170.54321.19760.079*
C110.5416 (3)0.2169 (3)0.6736 (2)0.0453 (9)
C120.4221 (4)0.2014 (3)0.6513 (3)0.0710 (13)
H120.37720.16290.68380.085*
C130.3681 (5)0.2434 (4)0.5801 (4)0.098 (2)
H130.28730.23310.56590.118*
C140.4336 (6)0.2999 (4)0.5309 (3)0.0874 (17)
H140.39800.32610.48260.105*
C150.5488 (5)0.3167 (4)0.5531 (3)0.0766 (15)
H150.59260.35590.52060.092*
C160.6043 (4)0.2762 (3)0.6241 (3)0.0585 (11)
H160.68440.28920.63850.070*
C170.8172 (3)0.1293 (3)0.7900 (2)0.0421 (9)
C180.8935 (3)0.2035 (3)0.7736 (2)0.0506 (10)
H180.86090.25910.75330.061*
C191.0165 (4)0.1954 (4)0.7871 (3)0.0637 (12)
H191.06540.24510.77470.076*
C201.0673 (4)0.1157 (4)0.8184 (3)0.0686 (13)
H201.15000.11170.82820.082*
C210.9949 (4)0.0407 (4)0.8356 (3)0.0689 (13)
H211.0291−0.01390.85670.083*
C220.8711 (4)0.0474 (3)0.8210 (3)0.0572 (11)
H220.8233−0.00340.83210.069*
C230.5185 (4)0.0463 (3)0.8402 (2)0.0472 (10)
C240.4280 (4)0.0796 (4)0.8874 (3)0.0631 (12)
H240.41310.14310.88950.076*
C250.3593 (4)0.0181 (5)0.9317 (3)0.0863 (17)
H250.29800.04050.96270.104*
C260.3825 (6)−0.0759 (5)0.9295 (4)0.097 (2)
H260.3369−0.11690.95900.117*
C270.4729 (7)−0.1092 (4)0.8837 (4)0.099 (2)
H270.4890−0.17250.88300.119*
C280.5397 (5)−0.0493 (3)0.8388 (3)0.0719 (14)
H280.5997−0.07270.80720.086*
C290.5361 (4)−0.0265 (3)0.6299 (3)0.0616 (12)
H29A0.4684−0.02620.66380.092*
H29B0.5566−0.08950.61710.092*
H29C0.51630.00660.57910.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04301 (18)0.03095 (17)0.04461 (17)−0.00319 (11)0.00217 (11)0.00156 (11)
N10.0432 (18)0.0352 (18)0.0464 (17)−0.0011 (14)0.0049 (14)−0.0061 (14)
O10.0639 (18)0.0323 (15)0.0577 (16)−0.0089 (13)0.0118 (13)−0.0063 (12)
O20.077 (2)0.0455 (18)0.0469 (16)−0.0086 (14)0.0153 (15)−0.0054 (13)
O30.0460 (16)0.0493 (17)0.0560 (16)−0.0015 (12)0.0073 (12)−0.0165 (13)
C10.044 (2)0.036 (2)0.049 (2)0.0019 (17)0.0013 (18)−0.0047 (18)
C20.046 (2)0.031 (2)0.044 (2)0.0039 (16)0.0027 (17)0.0016 (16)
C30.060 (3)0.037 (2)0.052 (2)−0.0028 (18)0.0107 (19)0.0076 (19)
C40.065 (3)0.054 (3)0.047 (2)0.004 (2)0.016 (2)0.007 (2)
C50.061 (3)0.048 (3)0.043 (2)0.011 (2)0.0046 (19)−0.0029 (19)
C60.044 (2)0.039 (2)0.045 (2)0.0043 (17)0.0054 (17)−0.0040 (17)
C70.065 (3)0.047 (3)0.062 (3)−0.010 (2)0.013 (2)−0.018 (2)
C80.075 (3)0.063 (3)0.082 (4)−0.010 (3)0.003 (3)−0.023 (3)
C90.092 (4)0.068 (4)0.061 (3)0.004 (3)0.002 (3)−0.027 (3)
C100.083 (3)0.070 (3)0.046 (2)0.009 (3)0.013 (2)−0.010 (2)
C110.049 (2)0.036 (2)0.051 (2)0.0026 (17)−0.0009 (18)−0.0014 (18)
C120.054 (3)0.065 (3)0.091 (4)−0.002 (2)−0.009 (2)0.011 (3)
C130.067 (4)0.096 (5)0.126 (5)0.007 (3)−0.044 (4)0.000 (4)
C140.112 (5)0.077 (4)0.069 (3)0.018 (4)−0.031 (3)0.004 (3)
C150.099 (4)0.076 (4)0.055 (3)0.014 (3)0.007 (3)0.012 (3)
C160.061 (3)0.055 (3)0.059 (3)0.001 (2)0.002 (2)0.010 (2)
C170.044 (2)0.044 (2)0.0381 (19)0.0039 (17)0.0000 (16)−0.0055 (17)
C180.047 (2)0.047 (3)0.057 (2)−0.0047 (19)−0.0012 (18)−0.005 (2)
C190.051 (3)0.069 (3)0.070 (3)−0.009 (2)0.000 (2)−0.007 (3)
C200.045 (3)0.090 (4)0.069 (3)0.009 (3)−0.006 (2)−0.012 (3)
C210.067 (3)0.067 (3)0.071 (3)0.024 (3)−0.008 (2)−0.001 (3)
C220.063 (3)0.045 (3)0.063 (3)0.002 (2)−0.003 (2)0.000 (2)
C230.056 (2)0.043 (2)0.042 (2)−0.0148 (18)−0.0002 (18)0.0018 (17)
C240.052 (3)0.069 (3)0.068 (3)−0.008 (2)0.003 (2)0.010 (2)
C250.056 (3)0.126 (5)0.078 (3)−0.019 (3)0.013 (3)0.021 (4)
C260.124 (5)0.089 (5)0.079 (4)−0.058 (4)0.010 (4)0.022 (4)
C270.168 (7)0.058 (3)0.072 (4)−0.042 (4)0.022 (4)0.006 (3)
C280.122 (4)0.041 (3)0.055 (3)−0.016 (3)0.021 (3)0.003 (2)
C290.055 (3)0.070 (3)0.059 (3)−0.011 (2)0.000 (2)−0.020 (2)
Geometric parameters (Å, °) top
Sn1—C172.135 (4)C13—H130.9300
Sn1—C112.138 (4)C14—C151.337 (7)
Sn1—O12.145 (3)C14—H140.9300
Sn1—C232.145 (4)C15—C161.394 (6)
Sn1—O32.437 (2)C15—H150.9300
N1—C21.323 (5)C16—H160.9300
N1—C61.376 (4)C17—C221.402 (5)
O1—C11.299 (4)C17—C181.402 (5)
O2—C11.222 (4)C18—C191.384 (6)
O3—C291.430 (4)C18—H180.9300
O3—H30.8200C19—C201.362 (7)
C1—C21.522 (5)C19—H190.9300
C2—C31.407 (5)C20—C211.387 (7)
C3—C41.372 (6)C20—H200.9300
C3—H3A0.9300C21—C221.393 (6)
C4—C51.414 (6)C21—H210.9300
C4—H40.9300C22—H220.9300
C5—C61.417 (5)C23—C241.387 (6)
C5—C101.427 (6)C23—C281.398 (6)
C6—C71.421 (5)C24—C251.397 (7)
C7—C81.366 (6)C24—H240.9300
C7—H70.9300C25—C261.379 (8)
C8—C91.397 (7)C25—H250.9300
C8—H80.9300C26—C271.373 (9)
C9—C101.349 (7)C26—H260.9300
C9—H90.9300C27—C281.374 (7)
C10—H100.9300C27—H270.9300
C11—C121.379 (6)C28—H280.9300
C11—C161.388 (6)C29—H29A0.9600
C12—C131.399 (7)C29—H29B0.9600
C12—H120.9300C29—H29C0.9600
C13—C141.378 (8)
C17—Sn1—C11121.34 (15)C12—C13—H13119.7
C17—Sn1—O196.50 (12)C15—C14—C13119.3 (5)
C11—Sn1—O1100.43 (13)C15—C14—H14120.3
C17—Sn1—C23118.77 (15)C13—C14—H14120.3
C11—Sn1—C23117.28 (15)C14—C15—C16121.1 (5)
O1—Sn1—C2388.95 (13)C14—C15—H15119.4
C17—Sn1—O385.81 (11)C16—C15—H15119.4
C11—Sn1—O383.72 (12)C11—C16—C15120.8 (4)
O1—Sn1—O3173.17 (9)C11—C16—H16119.6
C23—Sn1—O384.31 (12)C15—C16—H16119.6
C2—N1—C6118.1 (3)C22—C17—C18117.1 (4)
C1—O1—Sn1119.2 (2)C22—C17—Sn1121.0 (3)
C29—O3—Sn1126.5 (2)C18—C17—Sn1121.9 (3)
C29—O3—H3109.5C19—C18—C17121.0 (4)
Sn1—O3—H3123.7C19—C18—H18119.5
O2—C1—O1125.7 (4)C17—C18—H18119.5
O2—C1—C2120.4 (3)C20—C19—C18121.1 (4)
O1—C1—C2113.9 (3)C20—C19—H19119.4
N1—C2—C3123.5 (3)C18—C19—H19119.4
N1—C2—C1115.3 (3)C19—C20—C21119.6 (4)
C3—C2—C1121.2 (3)C19—C20—H20120.2
C4—C3—C2118.9 (4)C21—C20—H20120.2
C4—C3—H3A120.6C20—C21—C22119.9 (4)
C2—C3—H3A120.6C20—C21—H21120.1
C3—C4—C5119.9 (4)C22—C21—H21120.1
C3—C4—H4120.1C21—C22—C17121.3 (4)
C5—C4—H4120.1C21—C22—H22119.4
C4—C5—C6117.3 (3)C17—C22—H22119.4
C4—C5—C10124.1 (4)C24—C23—C28118.6 (4)
C6—C5—C10118.6 (4)C24—C23—Sn1119.8 (3)
N1—C6—C5122.3 (3)C28—C23—Sn1121.6 (3)
N1—C6—C7118.3 (3)C23—C24—C25120.3 (5)
C5—C6—C7119.4 (4)C23—C24—H24119.9
C8—C7—C6119.5 (4)C25—C24—H24119.9
C8—C7—H7120.2C26—C25—C24119.9 (5)
C6—C7—H7120.2C26—C25—H25120.1
C7—C8—C9121.1 (5)C24—C25—H25120.1
C7—C8—H8119.5C27—C26—C25120.2 (5)
C9—C8—H8119.5C27—C26—H26119.9
C10—C9—C8121.0 (4)C25—C26—H26119.9
C10—C9—H9119.5C26—C27—C28120.3 (6)
C8—C9—H9119.5C26—C27—H27119.8
C9—C10—C5120.4 (4)C28—C27—H27119.8
C9—C10—H10119.8C27—C28—C23120.8 (5)
C5—C10—H10119.8C27—C28—H28119.6
C12—C11—C16117.8 (4)C23—C28—H28119.6
C12—C11—Sn1119.7 (3)O3—C29—H29A109.5
C16—C11—Sn1122.3 (3)O3—C29—H29B109.5
C11—C12—C13120.3 (5)H29A—C29—H29B109.5
C11—C12—H12119.9O3—C29—H29C109.5
C13—C12—H12119.9H29A—C29—H29C109.5
C14—C13—C12120.6 (5)H29B—C29—H29C109.5
C14—C13—H13119.7
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.822.443.000 (4)127
O3—H3···N1i0.822.082.827 (4)151
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2.
Selected geometric parameters (Å, °) top
Sn1—C172.135 (4)Sn1—C232.145 (4)
Sn1—C112.138 (4)Sn1—O32.437 (2)
Sn1—O12.145 (3)
O1—Sn1—O3173.17 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.822.443.000 (4)127
O3—H3···N1i0.822.082.827 (4)151
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2.
Acknowledgements top

We acknowledge the financial support of the Shandong Province Science Foundation, and the State Key Laboratory of Crystalline Materials, Shandong University, China.

references
References top

Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

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

Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS, Inc., Madison, Wisconsin, USA.

Siemens (1996). SMART and SAINT. Siemens Analytical X-Ray Instrument Inc., Madison, Wisconsin, USA.