Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058229/hb2653sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058229/hb2653Isup2.hkl |
CCDC reference: 672689
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.031
- wR factor = 0.091
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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).
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. |
[Sn(CH3)2(C10H6NO2)Cl] | F(000) = 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 = 2.2–26.9° |
b = 10.245 (10) Å | µ = 2.07 mm−1 |
c = 13.763 (7) Å | T = 298 K |
β = 107.811 (10)° | 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) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 25.0°, θmin = 2.1° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.050P)2 + 1.111P] where P = (Fo2 + 2Fc2)/3 |
2370 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.64 e Å−3 |
[Sn(CH3)2(C10H6NO2)Cl] | V = 1355 (2) Å3 |
Mr = 356.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.093 (10) Å | µ = 2.07 mm−1 |
b = 10.245 (10) Å | T = 298 K |
c = 13.763 (7) Å | 0.43 × 0.22 × 0.10 mm |
β = 107.811 (10)° |
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 | 0 restraints |
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 |
154 parameters |
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 |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)2(C10H6NO2)Cl] |
Mr | 356.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.093 (10), 10.245 (10), 13.763 (7) |
β (°) | 107.811 (10) |
V (Å3) | 1355 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.07 |
Crystal size (mm) | 0.43 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.470, 0.820 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6777, 2370, 1864 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.092, 1.00 |
No. of reflections | 2370 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.64 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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) |
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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).