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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056851/hb2644sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056851/hb2644Isup2.hkl
Contains datablock I

CCDC reference: 672645

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.029
  • wR factor = 0.098
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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)]F(000) = 1120
Mr = 554.19Dx = 1.424 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5687 reflections
a = 11.1774 (11) Åθ = 2.3–26.9°
b = 14.3964 (12) ŵ = 1.02 mm1
c = 16.098 (2) ÅT = 298 K
β = 93.572 (2)°Block, 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)
Graphite monochromatorRint = 0.040
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1013
Tmin = 0.610, Tmax = 0.657k = 1714
12574 measured reflectionsl = 1919
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.777P]
where P = (Fo2 + 2Fc2)/3
4551 reflections(Δ/σ)max = 0.002
307 parametersΔρmax = 0.90 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
[Sn(C6H5)3(C10H6NO2)(CH4O)]V = 2585.3 (5) Å3
Mr = 554.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.1774 (11) ŵ = 1.02 mm1
b = 14.3964 (12) ÅT = 298 K
c = 16.098 (2) Å0.54 × 0.46 × 0.45 mm
β = 93.572 (2)°
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)] = 0.0290 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.00Δρmax = 0.90 e Å3
4551 reflectionsΔρmin = 0.47 e Å3
307 parameters
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)
H30.69840.00160.65590.075*
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)
H211.02910.01390.85670.083*
C220.8711 (4)0.0474 (3)0.8210 (3)0.0572 (11)
H220.82330.00340.83210.069*
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)
H260.33690.11690.95900.117*
C270.4729 (7)0.1092 (4)0.8837 (4)0.099 (2)
H270.48900.17250.88300.119*
C280.5397 (5)0.0493 (3)0.8388 (3)0.0719 (14)
H280.59970.07270.80720.086*
C290.5361 (4)0.0265 (3)0.6299 (3)0.0616 (12)
H29A0.46840.02620.66380.092*
H29B0.55660.08950.61710.092*
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, º) 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, º) 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 code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C10H6NO2)(CH4O)]
Mr554.19
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.1774 (11), 14.3964 (12), 16.098 (2)
β (°) 93.572 (2)
V3)2585.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.02
Crystal size (mm)0.54 × 0.46 × 0.45
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.610, 0.657
No. of measured, independent and
observed [I > 2σ(I)] reflections
12574, 4551, 3424
Rint0.040
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.099, 1.00
No. of reflections4551
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.90, 0.47

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) 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, º) 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 code: (i) x+3/2, y1/2, z+3/2.
 

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