Acta Cryst. (2007). E63, m3059 [ doi:10.1107/S1600536807058229 ]
The Sn atom in the title compound, [Sn(CH3)2(C10H6NO2)Cl], has a distorted SnC2NOCl trigonal-bipyramidal geometry with the quinoline N atom and Cl atom occupying the axial sites.
The reaction was carried out under nitrogen atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Dimethyltin 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 v/v) to yield colourless blocks of (I) (yield 85%; m.p. 422 K). Analysis calculated (%) for C12H12ClNO2Sn (Mr = 356.37): C, 40.44; H, 3.39; N, 3.93. found: C, 40.37; H, 3.42; N, 4.06.
The H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
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).
![[Figure 1]](./hb2653fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. |
| [Sn(CH3)2(C10H6NO2)Cl] | F000 = 696 |
| Mr = 356.37 | Dx = 1.747 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3020 reflections |
| a = 10.093 (10) Å | θ = 2.2–26.9º |
| b = 10.245 (10) Å | µ = 2.07 mm−1 |
| c = 13.763 (7) Å | T = 298 (2) K |
| β = 107.811 (10)º | Block, colourless |
| V = 1355 (2) Å3 | 0.43 × 0.22 × 0.10 mm |
| Z = 4 |
| Siemens SMART CCD diffractometer | 2370 independent reflections |
| Radiation source: fine-focus sealed tube | 1864 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| T = 298(2) K | θmax = 25.0º |
| ω scans | θmin = 2.1º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.470, Tmax = 0.820 | k = −11→12 |
| 6777 measured reflections | l = −16→12 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.050P)2 + 1.111P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max < 0.001 |
| 2370 reflections | Δρmax = 0.52 e Å−3 |
| 154 parameters | Δρmin = −0.64 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Sn(CH3)2(C10H6NO2)Cl] | V = 1355 (2) Å3 |
| Mr = 356.37 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 10.093 (10) Å | µ = 2.07 mm−1 |
| b = 10.245 (10) Å | T = 298 (2) K |
| c = 13.763 (7) Å | 0.43 × 0.22 × 0.10 mm |
| β = 107.811 (10)º |
| Siemens SMART CCD diffractometer | 2370 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1864 reflections with I > 2σ(I) |
| Tmin = 0.470, Tmax = 0.820 | Rint = 0.035 |
| 6777 measured reflections |
| R[F2 > 2σ(F2)] = 0.031 | 154 parameters |
| wR(F2) = 0.092 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 0.52 e Å−3 |
| 2370 reflections | Δρmin = −0.64 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.84595 (3) | 0.38500 (3) | 0.11961 (2) | 0.04570 (15) | |
| Cl1 | 0.9399 (2) | 0.58899 (17) | 0.20610 (15) | 0.1085 (7) | |
| N1 | 0.6902 (3) | 0.2501 (3) | −0.0062 (2) | 0.0404 (8) | |
| O1 | 0.7184 (3) | 0.5072 (3) | 0.0152 (2) | 0.0527 (8) | |
| O2 | 0.5316 (4) | 0.5410 (4) | −0.1171 (3) | 0.0745 (11) | |
| C1 | 0.6110 (5) | 0.4669 (5) | −0.0584 (4) | 0.0491 (11) | |
| C2 | 0.5919 (4) | 0.3224 (4) | −0.0701 (3) | 0.0432 (10) | |
| C3 | 0.4796 (5) | 0.2692 (5) | −0.1459 (3) | 0.0559 (12) | |
| H3 | 0.4110 | 0.3226 | −0.1876 | 0.067* | |
| C4 | 0.4729 (6) | 0.1371 (6) | −0.1573 (4) | 0.0630 (15) | |
| H4 | 0.3993 | 0.0996 | −0.2077 | 0.076* | |
| C5 | 0.5757 (5) | 0.0577 (5) | −0.0939 (4) | 0.0557 (12) | |
| C6 | 0.6834 (5) | 0.1170 (4) | −0.0167 (4) | 0.0472 (11) | |
| C7 | 0.7870 (5) | 0.0395 (5) | 0.0500 (4) | 0.0608 (13) | |
| H7 | 0.8583 | 0.0780 | 0.1016 | 0.073* | |
| C8 | 0.7814 (7) | −0.0936 (5) | 0.0380 (6) | 0.0799 (19) | |
| H8 | 0.8493 | −0.1453 | 0.0822 | 0.096* | |
| C9 | 0.6768 (8) | −0.1520 (6) | −0.0385 (6) | 0.085 (2) | |
| H9 | 0.6765 | −0.2423 | −0.0453 | 0.102* | |
| C10 | 0.5746 (8) | −0.0815 (6) | −0.1038 (5) | 0.0765 (19) | |
| H10 | 0.5045 | −0.1229 | −0.1545 | 0.092* | |
| C11 | 0.7655 (5) | 0.3133 (5) | 0.2328 (4) | 0.0623 (13) | |
| H11A | 0.6855 | 0.3638 | 0.2332 | 0.093* | |
| H11B | 0.8351 | 0.3197 | 0.2982 | 0.093* | |
| H11C | 0.7389 | 0.2237 | 0.2188 | 0.093* | |
| C12 | 1.0181 (5) | 0.3270 (6) | 0.0735 (5) | 0.0815 (18) | |
| H12A | 1.0249 | 0.3822 | 0.0188 | 0.122* | |
| H12B | 1.0060 | 0.2381 | 0.0505 | 0.122* | |
| H12C | 1.1016 | 0.3344 | 0.1301 | 0.122* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0431 (2) | 0.0443 (2) | 0.0489 (2) | −0.00363 (13) | 0.01283 (14) | 0.00114 (14) |
| Cl1 | 0.1292 (16) | 0.0709 (11) | 0.0931 (13) | −0.0353 (10) | −0.0139 (11) | −0.0156 (9) |
| N1 | 0.051 (2) | 0.035 (2) | 0.0390 (19) | 0.0010 (16) | 0.0183 (16) | −0.0001 (15) |
| O1 | 0.0593 (19) | 0.0362 (18) | 0.060 (2) | 0.0000 (14) | 0.0143 (16) | 0.0035 (15) |
| O2 | 0.079 (2) | 0.062 (2) | 0.072 (2) | 0.016 (2) | 0.007 (2) | 0.024 (2) |
| C1 | 0.056 (3) | 0.045 (3) | 0.050 (3) | 0.005 (2) | 0.021 (2) | 0.007 (2) |
| C2 | 0.048 (2) | 0.044 (3) | 0.040 (2) | −0.003 (2) | 0.0166 (19) | −0.001 (2) |
| C3 | 0.056 (3) | 0.071 (4) | 0.041 (3) | −0.007 (2) | 0.015 (2) | 0.001 (2) |
| C4 | 0.062 (3) | 0.084 (4) | 0.048 (3) | −0.028 (3) | 0.024 (2) | −0.023 (3) |
| C5 | 0.071 (3) | 0.053 (3) | 0.055 (3) | −0.018 (3) | 0.037 (3) | −0.018 (3) |
| C6 | 0.062 (3) | 0.035 (2) | 0.056 (3) | −0.004 (2) | 0.035 (2) | −0.005 (2) |
| C7 | 0.073 (3) | 0.041 (3) | 0.070 (3) | 0.008 (2) | 0.024 (3) | 0.002 (2) |
| C8 | 0.109 (5) | 0.038 (3) | 0.111 (5) | 0.017 (3) | 0.060 (4) | 0.011 (3) |
| C9 | 0.124 (6) | 0.036 (3) | 0.128 (6) | −0.017 (4) | 0.089 (5) | −0.022 (4) |
| C10 | 0.108 (5) | 0.055 (4) | 0.095 (5) | −0.027 (3) | 0.074 (4) | −0.028 (3) |
| C11 | 0.065 (3) | 0.072 (4) | 0.052 (3) | 0.012 (3) | 0.021 (2) | 0.007 (3) |
| C12 | 0.057 (3) | 0.082 (4) | 0.120 (5) | 0.012 (3) | 0.049 (3) | 0.029 (4) |
| Sn1—O1 | 2.040 (3) | C5—C10 | 1.433 (8) |
| Sn1—C11 | 2.098 (5) | C6—C7 | 1.407 (7) |
| Sn1—C12 | 2.109 (5) | C7—C8 | 1.373 (7) |
| Sn1—N1 | 2.390 (4) | C7—H7 | 0.9300 |
| Sn1—Cl1 | 2.448 (2) | C8—C9 | 1.379 (9) |
| N1—C2 | 1.333 (5) | C8—H8 | 0.9300 |
| N1—C6 | 1.371 (5) | C9—C10 | 1.351 (10) |
| O1—C1 | 1.304 (5) | C9—H9 | 0.9300 |
| O2—C1 | 1.215 (5) | C10—H10 | 0.9300 |
| C1—C2 | 1.495 (7) | C11—H11A | 0.9600 |
| C2—C3 | 1.395 (6) | C11—H11B | 0.9600 |
| C3—C4 | 1.362 (7) | C11—H11C | 0.9600 |
| C3—H3 | 0.9300 | C12—H12A | 0.9600 |
| C4—C5 | 1.396 (8) | C12—H12B | 0.9600 |
| C4—H4 | 0.9300 | C12—H12C | 0.9600 |
| C5—C6 | 1.404 (7) | ||
| O1—Sn1—C11 | 115.73 (17) | C6—C5—C10 | 119.0 (6) |
| O1—Sn1—C12 | 111.2 (2) | N1—C6—C5 | 120.8 (5) |
| C11—Sn1—C12 | 131.8 (2) | N1—C6—C7 | 119.3 (4) |
| O1—Sn1—N1 | 73.22 (14) | C5—C6—C7 | 119.9 (4) |
| C11—Sn1—N1 | 90.98 (18) | C8—C7—C6 | 119.1 (6) |
| C12—Sn1—N1 | 92.2 (2) | C8—C7—H7 | 120.4 |
| O1—Sn1—Cl1 | 83.42 (11) | C6—C7—H7 | 120.4 |
| C11—Sn1—Cl1 | 96.77 (17) | C7—C8—C9 | 121.1 (6) |
| C12—Sn1—Cl1 | 98.9 (2) | C7—C8—H8 | 119.4 |
| N1—Sn1—Cl1 | 156.47 (10) | C9—C8—H8 | 119.4 |
| C2—N1—C6 | 118.7 (4) | C10—C9—C8 | 121.8 (6) |
| C2—N1—Sn1 | 110.4 (3) | C10—C9—H9 | 119.1 |
| C6—N1—Sn1 | 130.7 (3) | C8—C9—H9 | 119.1 |
| C1—O1—Sn1 | 123.3 (3) | C9—C10—C5 | 119.1 (6) |
| O2—C1—O1 | 122.8 (4) | C9—C10—H10 | 120.5 |
| O2—C1—C2 | 120.6 (4) | C5—C10—H10 | 120.5 |
| O1—C1—C2 | 116.5 (4) | Sn1—C11—H11A | 109.5 |
| N1—C2—C3 | 123.2 (4) | Sn1—C11—H11B | 109.5 |
| N1—C2—C1 | 115.7 (4) | H11A—C11—H11B | 109.5 |
| C3—C2—C1 | 121.1 (4) | Sn1—C11—H11C | 109.5 |
| C4—C3—C2 | 118.4 (5) | H11A—C11—H11C | 109.5 |
| C4—C3—H3 | 120.8 | H11B—C11—H11C | 109.5 |
| C2—C3—H3 | 120.8 | Sn1—C12—H12A | 109.5 |
| C3—C4—C5 | 120.4 (5) | Sn1—C12—H12B | 109.5 |
| C3—C4—H4 | 119.8 | H12A—C12—H12B | 109.5 |
| C5—C4—H4 | 119.8 | Sn1—C12—H12C | 109.5 |
| C4—C5—C6 | 118.5 (5) | H12A—C12—H12C | 109.5 |
| C4—C5—C10 | 122.6 (6) | H12B—C12—H12C | 109.5 |
| Sn1—O1 | 2.040 (3) | Sn1—N1 | 2.390 (4) |
| Sn1—C11 | 2.098 (5) | Sn1—Cl1 | 2.448 (2) |
| Sn1—C12 | 2.109 (5) |
We acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, China.
Ma, C. L., Jiang, Q., Zhang, R. F. & Wang, D. Q. (2004). J. Chem. Soc. Dalton Trans. pp. 1832–1840.
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 Instruments, Inc., Madison, Wisconsin, USA.
Organotin esters of carboxylic acids are widely used as biocides, as fungicides and, in industry, as 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.
The molecular structure of (I) is shown in Fig. 1. The Sn1 assumes a trigonal-bipyramidal coordination geometry (Table 1) with atoms N1 and Cl1 in axial positions [N1—Sn1—Cl1 = 156.47 (10) °] and the C atoms of the two methyl groups and the ligand Cl atom in equatorial positions. Associated with the sum of the angles subtended at the Sn1 in the equatorial plane is 358.7°, indicating approximate coplanarity for these atoms;. The Sn—O and Sn—N distnaces in (I) are close to those in related compounds (Ma et al., 2004).