catena-Poly[[trimethyl­tin(IV)]-μ-2,4,6-trichloro­benzoato]

Abstract

In the title compound, [Sn(CH₃)₃(C₇H₂Cl₃O₂)]_n, the tin(IV) atom exhibits a slightly distorted trigonal-bipyramidal geometry with two O atoms of symmetry-related carboxyl­ate groups in the axial positions and three methyl groups in the equatorial positions. In the crystal structure, the metal atoms are linked by carboxyl­ate bridges into polymeric chains extending along the b axis.

Related literature

For related structures, see: Wang et al. (2007 ▶); Ma et al. (2006 ▶).

Experimental

Crystal data

• [Sn(CH₃)₃(C₇H₂Cl₃O₂)]

• M _r = 388.25

• Monoclinic,

• a = 9.8457 (10) Å

• b = 9.6891 (9) Å

• c = 15.3028 (19) Å

• β = 106.761 (1)°

• V = 1397.8 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 2.38 mm⁻¹

• T = 298 (2) K

• 0.42 × 0.18 × 0.08 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.434, T _max = 0.832

• 6983 measured reflections

• 2469 independent reflections

• 1996 reflections with I > 2σ(I)

• R _int = 0.025

Refinement

• R[F ² > 2σ(F ²)] = 0.028

• wR(F ²) = 0.085

• S = 1.01

• 2469 reflections

• 145 parameters

• H-atom parameters constrained

• Δρ_max = 0.68 e Å⁻³

• Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected bond lengths (Å).

Sn1—C9	2.107 (5)
Sn1—C10	2.116 (5)
Sn1—C8	2.123 (4)
Sn1—O1	2.212 (3)
Sn1—O2i	2.467 (3)

Symmetry code: (i) .

supplementary crystallographic information

Comment

Organoantin(IV) derivatives have recently attracted considerable attention due to the significant antimicrobial properties (Wang et al., 2007). As a part of our ongoing investigations in this field, we have synthesized the title compound and present its crystal structure here.

In the title compound (Fig. 1), the Sn—O bond distances (Table 1) are comparable to those found in related organotin carboxylates (Ma et al., 2006). The Sn atom assumes a slightly distorted trigonal-bipyramidal coordination geometry, provided by two O atoms of symmetry related carboxylate groups at the axial positions and three methyl groups at the equatorial positions. In the crystal structure, the metal atoms are linked by carboxylate bridges into polymeric chains extending along the b axis (Fig. 2).

Experimental

The reaction was carried out under nitrogen atmosphere. 2,4,6-Trichlorobenzoic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane/methanol (1:1 v/v) solution (yield 83%. m. p. 403K). Anal. Calcd (%) for C₁₀H₁₁Cl₃O₂Sn: C, 30.94; H, 2.86; O, 8.24; Sn, 30.58; Found (%): C, 30.89; H, 2.90; O, 8.31; Sn, 30.62.

Refinement

H atoms were positioned geometrically, with methyl C—H distances of 0.96 Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with U_iso(H) = 1.2 U_eq(C) or 1.5 U_eq(C) for the methyl groups.

Figures

Fig. 1.

The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. Symmetry code: (A) = -x + 1,y + 1/2,-z + 1/2.

Fig. 2.

View of the one-dimensional chain structure extending along the b axis.

Crystal data

[Sn(CH3)3(C7H2Cl3O2)]	F(000) = 752
Mr = 388.25	Dx = 1.845 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3337 reflections
a = 9.8457 (10) Å	θ = 2.5–27.6°
b = 9.6891 (9) Å	µ = 2.38 mm−1
c = 15.3028 (19) Å	T = 298 K
β = 106.761 (1)°	Block, colourless
V = 1397.8 (3) Å3	0.42 × 0.18 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	1996 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.434, Tmax = 0.832	k = −10→11
6983 measured reflections	l = −18→15

Refinement

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.048P)2 + 1.1107P] where P = (Fo2 + 2Fc2)/3
2469 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.41662 (3)	0.26723 (3)	0.24850 (2)	0.03954 (13)
Cl1	0.13395 (13)	−0.14643 (14)	0.30795 (8)	0.0553 (3)
Cl2	−0.17245 (14)	−0.41671 (14)	0.00986 (9)	0.0685 (4)
Cl3	0.21742 (14)	−0.04603 (14)	−0.01909 (8)	0.0589 (3)
O1	0.2441 (3)	0.1152 (3)	0.1981 (2)	0.0436 (7)
O2	0.4091 (3)	−0.0438 (3)	0.2076 (2)	0.0483 (8)
C1	0.2834 (4)	−0.0058 (4)	0.1860 (3)	0.0368 (9)
C2	0.1682 (4)	−0.1073 (4)	0.1414 (3)	0.0357 (9)
C3	0.0947 (4)	−0.1793 (4)	0.1922 (3)	0.0379 (9)
C4	−0.0092 (5)	−0.2761 (4)	0.1529 (3)	0.0416 (10)
H4	−0.0557	−0.3248	0.1881	0.050*
C5	−0.0410 (5)	−0.2974 (4)	0.0609 (3)	0.0429 (11)
C6	0.0256 (5)	−0.2269 (4)	0.0067 (3)	0.0449 (11)
H6	0.0004	−0.2414	−0.0560	0.054*
C7	0.1307 (4)	−0.1341 (4)	0.0483 (3)	0.0396 (10)
C8	0.2673 (5)	0.4245 (5)	0.2502 (4)	0.0582 (13)
H8A	0.3162	0.5044	0.2809	0.087*
H8B	0.2023	0.3917	0.2818	0.087*
H8C	0.2158	0.4484	0.1887	0.087*
C9	0.4924 (6)	0.2466 (5)	0.1337 (3)	0.0510 (12)
H9A	0.5867	0.2092	0.1523	0.077*
H9B	0.4938	0.3355	0.1062	0.077*
H9C	0.4312	0.1857	0.0902	0.077*
C10	0.5129 (6)	0.1758 (6)	0.3770 (3)	0.0617 (14)
H10A	0.6022	0.1359	0.3770	0.093*
H10B	0.4520	0.1051	0.3886	0.093*
H10C	0.5283	0.2449	0.4238	0.093*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Sn1	0.03773 (19)	0.0345 (2)	0.0475 (2)	−0.00090 (12)	0.01410 (14)	−0.00256 (13)
Cl1	0.0537 (7)	0.0745 (9)	0.0398 (7)	−0.0114 (6)	0.0167 (5)	−0.0052 (6)
Cl2	0.0641 (8)	0.0599 (8)	0.0692 (9)	−0.0214 (7)	−0.0003 (6)	−0.0076 (7)
Cl3	0.0717 (8)	0.0616 (8)	0.0511 (7)	−0.0064 (6)	0.0300 (6)	0.0062 (6)
O1	0.0357 (15)	0.0308 (16)	0.066 (2)	−0.0010 (12)	0.0176 (14)	−0.0100 (14)
O2	0.0367 (17)	0.0375 (17)	0.068 (2)	0.0041 (13)	0.0106 (14)	0.0015 (15)
C1	0.038 (2)	0.034 (2)	0.040 (2)	−0.0021 (18)	0.0155 (19)	0.0017 (18)
C2	0.035 (2)	0.028 (2)	0.042 (2)	0.0022 (17)	0.0089 (18)	−0.0017 (18)
C3	0.040 (2)	0.037 (2)	0.038 (2)	−0.0023 (19)	0.0133 (19)	−0.0009 (19)
C4	0.038 (2)	0.036 (2)	0.051 (3)	−0.0047 (18)	0.012 (2)	0.003 (2)
C5	0.039 (2)	0.033 (2)	0.051 (3)	−0.0032 (19)	0.005 (2)	−0.007 (2)
C6	0.049 (3)	0.045 (3)	0.038 (3)	0.004 (2)	0.009 (2)	−0.005 (2)
C7	0.041 (2)	0.035 (2)	0.045 (3)	0.0037 (18)	0.0144 (19)	0.0031 (19)
C8	0.045 (3)	0.045 (3)	0.086 (4)	−0.004 (2)	0.022 (3)	−0.019 (3)
C9	0.055 (3)	0.052 (3)	0.051 (3)	−0.002 (2)	0.023 (2)	0.001 (2)
C10	0.078 (4)	0.056 (3)	0.047 (3)	−0.014 (3)	0.011 (3)	0.004 (2)

Geometric parameters (Å, °)

Sn1—C9	2.107 (5)	C4—C5	1.366 (6)
Sn1—C10	2.116 (5)	C4—H4	0.9300
Sn1—C8	2.123 (4)	C5—C6	1.377 (7)
Sn1—O1	2.212 (3)	C6—C7	1.380 (6)
Sn1—O2i	2.467 (3)	C6—H6	0.9300
Cl1—C3	1.730 (4)	C8—H8A	0.9600
Cl2—C5	1.744 (4)	C8—H8B	0.9600
Cl3—C7	1.740 (4)	C8—H8C	0.9600
O1—C1	1.265 (5)	C9—H9A	0.9600
O2—C1	1.241 (5)	C9—H9B	0.9600
O2—Sn1ii	2.467 (3)	C9—H9C	0.9600
C1—C2	1.508 (5)	C10—H10A	0.9600
C2—C7	1.390 (6)	C10—H10B	0.9600
C2—C3	1.392 (6)	C10—H10C	0.9600
C3—C4	1.390 (6)
C9—Sn1—C10	124.3 (2)	C6—C5—Cl2	118.7 (4)
C9—Sn1—C8	119.4 (2)	C5—C6—C7	118.0 (4)
C10—Sn1—C8	114.6 (2)	C5—C6—H6	121.0
C9—Sn1—O1	93.83 (16)	C7—C6—H6	121.0
C10—Sn1—O1	97.96 (16)	C6—C7—C2	122.4 (4)
C8—Sn1—O1	91.00 (15)	C6—C7—Cl3	118.5 (4)
C9—Sn1—O2i	84.92 (15)	C2—C7—Cl3	119.1 (3)
C10—Sn1—O2i	88.16 (16)	Sn1—C8—H8A	109.5
C8—Sn1—O2i	83.90 (15)	Sn1—C8—H8B	109.5
O1—Sn1—O2i	173.28 (10)	H8A—C8—H8B	109.5
C1—O1—Sn1	115.6 (2)	Sn1—C8—H8C	109.5
C1—O2—Sn1ii	148.7 (3)	H8A—C8—H8C	109.5
O2—C1—O1	124.0 (4)	H8B—C8—H8C	109.5
O2—C1—C2	119.3 (4)	Sn1—C9—H9A	109.5
O1—C1—C2	116.6 (3)	Sn1—C9—H9B	109.5
C7—C2—C3	116.9 (4)	H9A—C9—H9B	109.5
C7—C2—C1	121.9 (4)	Sn1—C9—H9C	109.5
C3—C2—C1	121.2 (4)	H9A—C9—H9C	109.5
C4—C3—C2	122.1 (4)	H9B—C9—H9C	109.5
C4—C3—Cl1	119.1 (3)	Sn1—C10—H10A	109.5
C2—C3—Cl1	118.7 (3)	Sn1—C10—H10B	109.5
C5—C4—C3	118.0 (4)	H10A—C10—H10B	109.5
C5—C4—H4	121.0	Sn1—C10—H10C	109.5
C3—C4—H4	121.0	H10A—C10—H10C	109.5
C4—C5—C6	122.6 (4)	H10B—C10—H10C	109.5
C4—C5—Cl2	118.8 (4)
C9—Sn1—O1—C1	61.1 (3)	C1—C2—C3—Cl1	2.0 (5)
C10—Sn1—O1—C1	−64.4 (3)	C2—C3—C4—C5	−1.5 (7)
C8—Sn1—O1—C1	−179.3 (3)	Cl1—C3—C4—C5	178.2 (3)
Sn1ii—O2—C1—O1	154.5 (4)	C3—C4—C5—C6	−0.1 (7)
Sn1ii—O2—C1—C2	−26.3 (8)	C3—C4—C5—Cl2	−179.2 (3)
Sn1—O1—C1—O2	6.1 (5)	C4—C5—C6—C7	1.7 (7)
Sn1—O1—C1—C2	−173.0 (3)	Cl2—C5—C6—C7	−179.2 (3)
O2—C1—C2—C7	−82.9 (5)	C5—C6—C7—C2	−1.8 (7)
O1—C1—C2—C7	96.3 (5)	C5—C6—C7—Cl3	179.1 (3)
O2—C1—C2—C3	96.8 (5)	C3—C2—C7—C6	0.2 (6)
O1—C1—C2—C3	−84.0 (5)	C1—C2—C7—C6	179.9 (4)
C7—C2—C3—C4	1.5 (6)	C3—C2—C7—Cl3	179.3 (3)
C1—C2—C3—C4	−178.2 (4)	C1—C2—C7—Cl3	−1.0 (5)
C7—C2—C3—Cl1	−178.3 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.