Chloridodimeth­yl(quinaldato)tin(IV)

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.031
• wR factor = 0.091
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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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

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S1. Comment

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).

Related literature

For related materials, see: Ma et al. (2004).

S2. Experimental

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.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

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

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Chloridodimethyl(quinaldato)tin(IV)

Crystal data

[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) Å^3	0.43 × 0.22 × 0.10 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 1.111P] where P = (Fo^2 + 2Fc^2)/3
2370 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.64 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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