catena-Poly[[trimethyl-tin(IV)]-μ-[(E)-2-methyl-3-(3-methyl-phen-yl)acrylato-κO:O']].

The title trimethyl-tin(IV) carboxyl-ate, [Sn(CH(3))(3)(C(11)H(11)O(2))](n), is a carboxyl-ate-bridged polymer in which the Sn atom exists in a trans-C(3)SnO(2) trigonal bipyramidal coordination. One Sn-O bond is a covalent bond [2.114 (2) Å], whereas the other is a dative bond [2.607 (2) Å]. The polymeric chain propagates along the b axis of the monoclinic unit cell.

Related literature

For related crystal structures, see: Muhammad et al. (2008a ▶,b ▶); Niaz et al. (2008 ▶); Tahir et al. (1997a ▶,b ▶).

Experimental

Crystal data

[Sn(CH3)3(C11H11O2)]

M = 339.01

Monoclinic,

a = 12.9530 (6) Å

b = 9.8756 (4) Å

c = 24.0728 (10) Å

β = 101.301 (2)°

V = 3019.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.68 mm−1

T = 296 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.705, T max = 0.781

14486 measured reflections

3348 independent reflections

2874 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.068

S = 1.01

3348 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019533/ng2468sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019533/ng2468Isup2.hkl

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

[Sn(CH3)3(C11H11O2)]	F000 = 1360
Mr = 339.01	Dx = 1.491 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3348 reflections
a = 12.9530 (6) Å	θ = 2.6–27.1º
b = 9.8756 (4) Å	µ = 1.68 mm−1
c = 24.0728 (10) Å	T = 296 (2) K
β = 101.301 (2)º	Prismatic, colourless
V = 3019.7 (2) Å3	0.25 × 0.18 × 0.15 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 7.5 pixels mm-1	θmax = 27.2º
T = 296(2) K	θmin = 2.6º
ω sans scans	h = −16→15
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −7→12
Tmin = 0.705, Tmax = 0.781	l = −30→30
14486 measured reflections

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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0374P)2 + 3.5913P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3348 reflections	Δρmax = 0.63 e Å−3
145 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Sn1	0.28429 (1)	−0.16993 (2)	0.22816 (1)	0.0380 (1)
O1	0.32929 (16)	−0.03474 (18)	0.16907 (8)	0.0498 (6)
O2	0.26730 (17)	0.1483 (2)	0.20361 (9)	0.0529 (7)
C1	0.3143 (2)	0.0940 (3)	0.17022 (10)	0.0389 (7)
C2	0.3576 (2)	0.1747 (2)	0.12708 (11)	0.0401 (8)
C3	0.3324 (3)	0.3224 (3)	0.12430 (15)	0.0591 (10)
C4	0.4185 (2)	0.1119 (3)	0.09665 (11)	0.0426 (8)
C5	0.4713 (2)	0.1667 (3)	0.05244 (12)	0.0482 (9)
C6	0.5691 (3)	0.1139 (4)	0.04886 (14)	0.0663 (11)
C7	0.6223 (3)	0.1596 (5)	0.00784 (19)	0.0870 (18)
C8	0.5750 (3)	0.2546 (5)	−0.03080 (15)	0.0809 (15)
C9	0.4775 (3)	0.3064 (4)	−0.02935 (13)	0.0663 (11)
C10	0.4254 (3)	0.2612 (3)	0.01229 (12)	0.0534 (10)
C11	0.42742 (14)	0.40923 (17)	−0.07152 (7)	0.0932 (18)
C12	0.35163 (14)	−0.33276 (17)	0.19080 (7)	0.0624 (11)
C13	0.38060 (14)	−0.08820 (17)	0.30121 (7)	0.0547 (10)
C14	0.12000 (14)	−0.14855 (17)	0.20410 (7)	0.0586 (10)
H3A	0.33496	0.35644	0.16190	0.0885*
H3B	0.26305	0.33584	0.10207	0.0885*
H3C	0.38277	0.36974	0.10716	0.0885*
H4	0.42933	0.02018	0.10434	0.0511*
H6	0.59915	0.04728	0.07422	0.0792*
H7	0.68900	0.12660	0.00642	0.1042*
H8	0.61025	0.28430	−0.05866	0.0972*
H10	0.35872	0.29454	0.01336	0.0640*
H11A	0.37070	0.45259	−0.05805	0.1396*
H11B	0.40055	0.36550	−0.10702	0.1396*
H11C	0.47878	0.47577	−0.07662	0.1396*
H12A	0.30201	−0.40592	0.18350	0.0935*
H12B	0.41411	−0.36295	0.21610	0.0935*
H12C	0.36936	−0.30341	0.15582	0.0935*
H13A	0.34336	−0.01717	0.31612	0.0820*
H13B	0.44368	−0.05221	0.29160	0.0820*
H13C	0.39864	−0.15800	0.32919	0.0820*
H14A	0.09961	−0.06049	0.21497	0.0879*
H14B	0.08599	−0.21672	0.22256	0.0879*
H14C	0.09943	−0.15869	0.16378	0.0879*

	U11	U22	U33	U12	U13	U23
Sn1	0.0438 (1)	0.0315 (1)	0.0422 (1)	−0.0025 (1)	0.0169 (1)	−0.0026 (1)
O1	0.0662 (12)	0.0339 (9)	0.0574 (11)	−0.0025 (9)	0.0322 (10)	0.0049 (8)
O2	0.0681 (13)	0.0464 (11)	0.0518 (11)	0.0016 (9)	0.0307 (10)	−0.0030 (9)
C1	0.0445 (14)	0.0348 (12)	0.0393 (12)	−0.0037 (11)	0.0131 (11)	−0.0012 (10)
C2	0.0499 (15)	0.0326 (12)	0.0405 (13)	−0.0067 (11)	0.0152 (11)	0.0005 (10)
C3	0.086 (2)	0.0339 (14)	0.0670 (19)	−0.0010 (14)	0.0383 (18)	0.0022 (13)
C4	0.0512 (15)	0.0386 (13)	0.0409 (13)	−0.0029 (12)	0.0162 (11)	0.0015 (11)
C5	0.0548 (16)	0.0507 (16)	0.0432 (14)	−0.0101 (13)	0.0196 (12)	−0.0023 (12)
C6	0.063 (2)	0.082 (2)	0.0602 (19)	0.0021 (18)	0.0278 (16)	0.0043 (18)
C7	0.068 (2)	0.126 (4)	0.078 (3)	−0.014 (2)	0.041 (2)	−0.008 (3)
C8	0.083 (3)	0.115 (3)	0.0525 (19)	−0.036 (2)	0.0324 (19)	0.002 (2)
C9	0.081 (2)	0.075 (2)	0.0420 (16)	−0.0339 (19)	0.0099 (15)	0.0009 (15)
C10	0.0604 (18)	0.0567 (18)	0.0434 (14)	−0.0169 (14)	0.0111 (13)	0.0004 (13)
C11	0.121 (4)	0.100 (3)	0.053 (2)	−0.040 (3)	0.003 (2)	0.023 (2)
C12	0.085 (2)	0.0397 (15)	0.075 (2)	0.0003 (15)	0.0463 (19)	−0.0039 (14)
C13	0.0519 (16)	0.0603 (18)	0.0517 (16)	−0.0072 (14)	0.0099 (13)	−0.0042 (14)
C14	0.0489 (16)	0.0635 (19)	0.0629 (18)	−0.0053 (14)	0.0095 (14)	0.0069 (15)

Sn1—O1	2.1144 (19)	C3—H3B	0.9600
Sn1—C12	2.1126 (17)	C3—H3C	0.9600
Sn1—C13	2.1072 (17)	C4—H4	0.9300
Sn1—C14	2.1037 (18)	C6—H6	0.9300
Sn1—O2i	2.607 (2)	C7—H7	0.9300
O1—C1	1.287 (3)	C8—H8	0.9300
O2—C1	1.223 (3)	C10—H10	0.9300
C1—C2	1.502 (4)	C11—H11A	0.9600
C2—C3	1.493 (4)	C11—H11B	0.9600
C2—C4	1.330 (4)	C11—H11C	0.9600
C4—C5	1.476 (4)	C12—H12A	0.9600
C5—C6	1.388 (5)	C12—H12B	0.9600
C5—C10	1.391 (4)	C12—H12C	0.9600
C6—C7	1.386 (6)	C13—H13A	0.9600
C7—C8	1.378 (6)	C13—H13B	0.9600
C8—C9	1.369 (6)	C13—H13C	0.9600
C9—C10	1.387 (5)	C14—H14A	0.9600
C9—C11	1.492 (4)	C14—H14B	0.9600
C3—H3A	0.9600	C14—H14C	0.9600
O1—Sn1—C12	90.17 (7)	C5—C4—H4	115.00
O1—Sn1—C13	97.09 (7)	C5—C6—H6	120.00
O1—Sn1—C14	98.56 (7)	C7—C6—H6	120.00
O1—Sn1—O2i	175.64 (7)	C6—C7—H7	120.00
C12—Sn1—C13	114.87 (7)	C8—C7—H7	120.00
C12—Sn1—C14	116.04 (7)	C7—C8—H8	119.00
C13—Sn1—C14	126.36 (7)	C9—C8—H8	119.00
Sn1—O1—C1	123.13 (17)	C5—C10—H10	119.00
Sn1ii—O2—C1	159.7 (2)	C9—C10—H10	119.00
O1—C1—O2	122.9 (2)	C9—C11—H11A	109.00
O1—C1—C2	115.5 (2)	C9—C11—H11B	109.00
O2—C1—C2	121.5 (3)	C9—C11—H11C	109.00
C1—C2—C3	116.2 (2)	H11A—C11—H11B	109.00
C1—C2—C4	118.4 (2)	H11A—C11—H11C	109.00
C3—C2—C4	125.4 (3)	H11B—C11—H11C	109.00
C2—C4—C5	129.4 (3)	Sn1—C12—H12A	109.00
C4—C5—C6	117.7 (3)	Sn1—C12—H12B	109.00
C4—C5—C10	123.5 (3)	Sn1—C12—H12C	109.00
C6—C5—C10	118.7 (3)	H12A—C12—H12B	109.00
C5—C6—C7	120.6 (3)	H12A—C12—H12C	109.00
C6—C7—C8	119.1 (4)	H12B—C12—H12C	109.00
C7—C8—C9	121.8 (4)	Sn1—C13—H13A	109.00
C8—C9—C10	118.7 (3)	Sn1—C13—H13B	109.00
C8—C9—C11	121.2 (3)	Sn1—C13—H13C	109.00
C10—C9—C11	120.2 (3)	H13A—C13—H13B	109.00
C5—C10—C9	121.1 (3)	H13A—C13—H13C	109.00
C2—C3—H3A	109.00	H13B—C13—H13C	109.00
C2—C3—H3B	109.00	Sn1—C14—H14A	109.00
C2—C3—H3C	110.00	Sn1—C14—H14B	109.00
H3A—C3—H3B	109.00	Sn1—C14—H14C	109.00
H3A—C3—H3C	110.00	H14A—C14—H14B	109.00
H3B—C3—H3C	109.00	H14A—C14—H14C	109.00
C2—C4—H4	115.00	H14B—C14—H14C	109.00
C12—Sn1—O1—C1	−176.6 (2)	C1—C2—C4—C5	−179.4 (3)
C13—Sn1—O1—C1	−61.5 (2)	C3—C2—C4—C5	−2.8 (5)
C14—Sn1—O1—C1	67.0 (2)	C2—C4—C5—C6	145.1 (3)
C12—Sn1—O2i—C1i	−157.4 (5)	C2—C4—C5—C10	−39.2 (5)
C13—Sn1—O2i—C1i	87.2 (5)	C4—C5—C6—C7	179.2 (3)
C14—Sn1—O2i—C1i	−40.4 (5)	C10—C5—C6—C7	3.3 (5)
Sn1—O1—C1—O2	−4.3 (4)	C4—C5—C10—C9	−178.1 (3)
Sn1—O1—C1—C2	176.30 (16)	C6—C5—C10—C9	−2.5 (5)
Sn1ii—O2—C1—O1	146.2 (4)	C5—C6—C7—C8	−2.5 (6)
Sn1ii—O2—C1—C2	−34.4 (7)	C6—C7—C8—C9	0.9 (7)
O1—C1—C2—C3	174.6 (3)	C7—C8—C9—C10	−0.1 (6)
O1—C1—C2—C4	−8.5 (4)	C7—C8—C9—C11	180.0 (4)
O2—C1—C2—C3	−4.8 (4)	C8—C9—C10—C5	0.9 (5)
O2—C1—C2—C4	172.1 (3)	C11—C9—C10—C5	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.9300	2.2800	2.695 (3)	107.00

Sn1—O1	2.1144 (19)
Sn1—C12	2.1126 (17)
Sn1—C13	2.1072 (17)
Sn1—C14	2.1037 (18)
Sn1—O2i	2.607 (2)

O1—Sn1—C12	90.17 (7)
O1—Sn1—C13	97.09 (7)
O1—Sn1—C14	98.56 (7)
O1—Sn1—O2i	175.64 (7)
C12—Sn1—C13	114.87 (7)
C12—Sn1—C14	116.04 (7)
C13—Sn1—C14	126.36 (7)

Symmetry code: (i) .