catena-Poly­[[tri­methyl­tin(IV)]-μ-2,3-bis(4-chloro­phenyl)­propenoato-κ²O:O′]

The title compound, [Sn(CH₃)₃(C₁₅H₉Cl₂O₂)]_n, forms polymeric chains involving both O atoms of the carboxyl­ate group. The coordination geometry around the Sn atom is distorted trigonal–bipyramidal. The three methyl C atoms occupy the equatorial positions, with Sn—C distances of 2.113 (3)–2.124 (2) Å, and two O atoms, including one from a symmetry-related mol­ecule, are at the axial positions, with Sn—O distances of 2.152 (2) and 2.454 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.073
• Data-to-parameter ratio = 21.5

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

catena-Poly[[trimethyltin(IV)]-µ-2,3-bis(4-chlorophenyl)propenoato-κ²O:O']

Crystal data

[Sn(CH3)3(C15H9Cl2O2)]	F(000) = 904
Mr = 455.91	Dx = 1.644 Mg m^−3
Monoclinic, P21/c	Melting point: 423-425 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.238 (2) Å	Cell parameters from 15524 reflections
b = 10.435 (2) Å	θ = 2.9–28.3°
c = 19.120 (4) Å	µ = 1.68 mm^−1
β = 91.456 (11)°	T = 173 K
V = 1842.5 (7) Å^3	Prism, colorless
Z = 4	0.20 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer	4528 independent reflections
Radiation source: fine-focus sealed tube	4032 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω and φ scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.723, Tmax = 0.767	k = −13→13
15524 measured reflections	l = −25→24

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 1.52P] where P = (Fo^2 + 2Fc^2)/3
4528 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.47380 (2)	−0.214130 (14)	0.235513 (7)	0.02155 (6)
Cl1	0.18559 (10)	0.62174 (6)	0.00670 (4)	0.04760 (19)
Cl2	−0.06983 (8)	0.01151 (9)	−0.23734 (4)	0.0503 (2)
O1	0.4102 (2)	−0.08748 (16)	0.15140 (9)	0.0363 (4)
O2	0.4556 (2)	0.11393 (16)	0.18300 (9)	0.0302 (4)
C1	0.4081 (3)	−0.1056 (2)	0.32321 (12)	0.0279 (5)
H1A	0.4833	−0.1100	0.3602	0.042*
H1B	0.3174	−0.1407	0.3406	0.042*
H1C	0.3932	−0.0161	0.3092	0.042*
C2	0.3269 (3)	−0.3494 (2)	0.19145 (13)	0.0324 (5)
H2A	0.3569	−0.3720	0.1442	0.049*
H2B	0.2295	−0.3123	0.1891	0.049*
H2C	0.3264	−0.4266	0.2206	0.049*
C3	0.6923 (3)	−0.2171 (3)	0.20542 (15)	0.0348 (6)
H3C	0.6980	−0.1924	0.1561	0.052*
H3B	0.7316	−0.3037	0.2118	0.052*
H3A	0.7486	−0.1567	0.2344	0.052*
C4	0.4059 (3)	0.0336 (2)	0.14166 (11)	0.0225 (4)
C5	0.3319 (2)	0.0754 (2)	0.07413 (11)	0.0204 (4)
C6	0.2905 (3)	−0.0139 (2)	0.02733 (11)	0.0221 (4)
H6	0.3217	−0.0987	0.0378	0.027*
C7	0.3075 (3)	0.2146 (2)	0.06228 (11)	0.0214 (4)
C8	0.2123 (3)	0.2832 (2)	0.10348 (12)	0.0252 (5)
H8	0.1722	0.2434	0.1433	0.030*
C9	0.1752 (3)	0.4089 (2)	0.08712 (13)	0.0288 (5)
H9	0.1087	0.4547	0.1148	0.035*
C10	0.2367 (3)	0.4661 (2)	0.02985 (13)	0.0296 (5)
C11	0.3355 (3)	0.4027 (2)	−0.01040 (13)	0.0318 (5)
H11	0.3789	0.4446	−0.0487	0.038*
C12	0.3710 (3)	0.2762 (2)	0.00587 (13)	0.0261 (5)
H12	0.4389	0.2315	−0.0216	0.031*
C13	0.2038 (3)	0.0003 (2)	−0.03787 (11)	0.0218 (4)
C14	0.1008 (3)	0.0970 (2)	−0.04908 (12)	0.0257 (5)
H14	0.0887	0.1612	−0.0145	0.031*
C15	0.0161 (3)	0.1001 (3)	−0.11026 (13)	0.0294 (5)
H15	−0.0530	0.1664	−0.1178	0.035*
C16	0.0338 (3)	0.0055 (3)	−0.15982 (12)	0.0319 (6)
C17	0.1318 (3)	−0.0922 (3)	−0.14996 (13)	0.0321 (5)
H17	0.1414	−0.1572	−0.1843	0.039*
C18	0.2167 (3)	−0.0943 (2)	−0.08892 (12)	0.0279 (5)
H18	0.2849	−0.1614	−0.0818	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02916 (10)	0.01563 (9)	0.01960 (9)	−0.00053 (6)	−0.00428 (6)	−0.00021 (5)
Cl1	0.0738 (5)	0.0186 (3)	0.0493 (4)	0.0074 (3)	−0.0177 (4)	0.0074 (3)
Cl2	0.0442 (4)	0.0725 (5)	0.0333 (3)	−0.0054 (4)	−0.0188 (3)	−0.0030 (3)
O1	0.0659 (13)	0.0173 (8)	0.0249 (8)	0.0038 (8)	−0.0127 (8)	0.0030 (7)
O2	0.0399 (10)	0.0245 (8)	0.0257 (8)	−0.0009 (7)	−0.0099 (7)	−0.0037 (7)
C1	0.0362 (13)	0.0238 (11)	0.0236 (11)	0.0043 (10)	−0.0012 (10)	−0.0020 (9)
C2	0.0373 (14)	0.0271 (12)	0.0321 (12)	−0.0054 (11)	−0.0111 (10)	−0.0014 (10)
C3	0.0346 (14)	0.0372 (15)	0.0329 (13)	−0.0035 (11)	0.0045 (11)	0.0029 (10)
C4	0.0276 (11)	0.0206 (11)	0.0192 (9)	0.0026 (9)	−0.0015 (8)	0.0002 (8)
C5	0.0229 (11)	0.0183 (10)	0.0201 (10)	−0.0007 (8)	−0.0010 (8)	0.0021 (8)
C6	0.0261 (11)	0.0185 (10)	0.0218 (10)	0.0019 (9)	−0.0009 (9)	0.0017 (8)
C7	0.0265 (11)	0.0175 (10)	0.0197 (10)	−0.0020 (8)	−0.0069 (9)	0.0026 (8)
C8	0.0306 (12)	0.0218 (12)	0.0228 (11)	−0.0011 (9)	−0.0029 (9)	0.0009 (8)
C9	0.0347 (13)	0.0214 (11)	0.0300 (12)	0.0027 (10)	−0.0044 (10)	−0.0039 (9)
C10	0.0406 (14)	0.0152 (10)	0.0322 (12)	−0.0011 (10)	−0.0140 (11)	0.0046 (9)
C11	0.0400 (14)	0.0246 (12)	0.0306 (12)	−0.0066 (11)	−0.0049 (11)	0.0103 (10)
C12	0.0281 (12)	0.0235 (12)	0.0266 (11)	−0.0035 (9)	−0.0040 (9)	0.0022 (9)
C13	0.0252 (11)	0.0206 (10)	0.0195 (10)	−0.0032 (9)	0.0000 (8)	0.0009 (8)
C14	0.0240 (11)	0.0268 (12)	0.0263 (11)	−0.0001 (9)	−0.0017 (9)	−0.0003 (9)
C15	0.0227 (11)	0.0355 (13)	0.0298 (12)	−0.0010 (10)	−0.0044 (9)	0.0043 (10)
C16	0.0282 (12)	0.0437 (15)	0.0235 (11)	−0.0116 (11)	−0.0053 (10)	0.0015 (10)
C17	0.0409 (14)	0.0301 (13)	0.0252 (11)	−0.0053 (11)	−0.0026 (10)	−0.0077 (10)
C18	0.0345 (13)	0.0221 (11)	0.0269 (11)	0.0004 (10)	−0.0008 (10)	−0.0018 (9)

Geometric parameters (Å, º)

Sn1—C3	2.113 (3)	C6—C13	1.472 (3)
Sn1—C2	2.118 (2)	C6—H6	0.9500
Sn1—C1	2.124 (2)	C7—C8	1.393 (3)
Sn1—O1	2.152 (2)	C7—C12	1.398 (3)
Sn1—O2^i	2.454 (2)	C8—C9	1.390 (3)
Cl1—C10	1.745 (2)	C8—H8	0.9500
Cl2—C16	1.745 (2)	C9—C10	1.382 (4)
O1—C4	1.277 (3)	C9—H9	0.9500
O2—C4	1.233 (3)	C10—C11	1.378 (4)
O2—Sn1^ii	2.454 (2)	C11—C12	1.393 (3)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—C18	1.395 (3)
C2—H2A	0.9800	C13—C14	1.400 (3)
C2—H2B	0.9800	C14—C15	1.391 (3)
C2—H2C	0.9800	C14—H14	0.9500
C3—H3C	0.9800	C15—C16	1.381 (4)
C3—H3B	0.9800	C15—H15	0.9500
C3—H3A	0.9800	C16—C17	1.373 (4)
C4—C5	1.510 (3)	C17—C18	1.390 (3)
C5—C6	1.341 (3)	C17—H17	0.9500
C5—C7	1.486 (3)	C18—H18	0.9500
C3—Sn1—C2	119.25 (11)	C13—C6—H6	115.3
C3—Sn1—C1	121.11 (11)	C8—C7—C12	118.9 (2)
C2—Sn1—C1	118.44 (11)	C8—C7—C5	120.8 (2)
C3—Sn1—O1	92.87 (10)	C12—C7—C5	120.1 (2)
C2—Sn1—O1	87.25 (9)	C9—C8—C7	120.9 (2)
C1—Sn1—O1	100.64 (8)	C9—C8—H8	119.6
C3—Sn1—O2^i	85.50 (9)	C7—C8—H8	119.6
C2—Sn1—O2^i	85.56 (8)	C10—C9—C8	118.8 (2)
C1—Sn1—O2^i	88.01 (8)	C10—C9—H9	120.6
O1—Sn1—O2^i	170.69 (6)	C8—C9—H9	120.6
C4—O1—Sn1	136.32 (15)	C11—C10—C9	121.8 (2)
C4—O2—Sn1^ii	173.24 (17)	C11—C10—Cl1	119.0 (2)
Sn1—C1—H1A	109.5	C9—C10—Cl1	119.3 (2)
Sn1—C1—H1B	109.5	C10—C11—C12	119.1 (2)
H1A—C1—H1B	109.5	C10—C11—H11	120.5
Sn1—C1—H1C	109.5	C12—C11—H11	120.5
H1A—C1—H1C	109.5	C11—C12—C7	120.5 (2)
H1B—C1—H1C	109.5	C11—C12—H12	119.8
Sn1—C2—H2A	109.5	C7—C12—H12	119.8
Sn1—C2—H2B	109.5	C18—C13—C14	118.2 (2)
H2A—C2—H2B	109.5	C18—C13—C6	117.9 (2)
Sn1—C2—H2C	109.5	C14—C13—C6	123.7 (2)
H2A—C2—H2C	109.5	C15—C14—C13	120.8 (2)
H2B—C2—H2C	109.5	C15—C14—H14	119.6
Sn1—C3—H3C	109.5	C13—C14—H14	119.6
Sn1—C3—H3B	109.5	C16—C15—C14	119.1 (2)
H3C—C3—H3B	109.5	C16—C15—H15	120.5
Sn1—C3—H3A	109.5	C14—C15—H15	120.5
H3C—C3—H3A	109.5	C17—C16—C15	121.7 (2)
H3B—C3—H3A	109.5	C17—C16—Cl2	119.3 (2)
O2—C4—O1	124.7 (2)	C15—C16—Cl2	119.0 (2)
O2—C4—C5	120.3 (2)	C16—C17—C18	118.9 (2)
O1—C4—C5	114.97 (19)	C16—C17—H17	120.6
C6—C5—C7	122.5 (2)	C18—C17—H17	120.6
C6—C5—C4	119.0 (2)	C17—C18—C13	121.4 (2)
C7—C5—C4	118.45 (19)	C17—C18—H18	119.3
C5—C6—C13	129.4 (2)	C13—C18—H18	119.3
C5—C6—H6	115.3
C3—Sn1—O1—C4	−87.1 (3)	C8—C9—C10—Cl1	177.46 (18)
C2—Sn1—O1—C4	153.7 (3)	C9—C10—C11—C12	1.9 (4)
C1—Sn1—O1—C4	35.3 (3)	Cl1—C10—C11—C12	−176.78 (19)
Sn1—O1—C4—O2	7.0 (4)	C10—C11—C12—C7	−0.1 (4)
Sn1—O1—C4—C5	−172.26 (18)	C8—C7—C12—C11	−2.3 (4)
O2—C4—C5—C6	174.1 (2)	C5—C7—C12—C11	172.6 (2)
O1—C4—C5—C6	−6.6 (3)	C5—C6—C13—C18	158.1 (2)
O2—C4—C5—C7	−6.1 (3)	C5—C6—C13—C14	−27.4 (4)
O1—C4—C5—C7	173.3 (2)	C18—C13—C14—C15	−1.4 (4)
C7—C5—C6—C13	−7.2 (4)	C6—C13—C14—C15	−175.9 (2)
C4—C5—C6—C13	172.7 (2)	C13—C14—C15—C16	0.6 (4)
C6—C5—C7—C8	113.2 (3)	C14—C15—C16—C17	0.7 (4)
C4—C5—C7—C8	−66.6 (3)	C14—C15—C16—Cl2	−178.64 (19)
C6—C5—C7—C12	−61.6 (3)	C15—C16—C17—C18	−1.0 (4)
C4—C5—C7—C12	118.6 (2)	Cl2—C16—C17—C18	178.3 (2)
C12—C7—C8—C9	3.1 (3)	C16—C17—C18—C13	0.2 (4)
C5—C7—C8—C9	−171.8 (2)	C14—C13—C18—C17	1.1 (4)
C7—C8—C9—C10	−1.3 (4)	C6—C13—C18—C17	175.9 (2)
C8—C9—C10—C11	−1.3 (4)

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