catena-Poly[[trimethyl-tin(IV)]-μ-cyclo-hex-3-ene-1-carboxyl-ato].

The title compound, [Sn(CH(3))(3)(C(7)H(9)O(2))](n), forms an extended zigzag chain structure propagating parallel to [010]. The Sn atom is in a slightly distorted trigonal-bipyramidal coordination environment with two carboxyl-ate O atoms in the axial and the three methyl groups in equatorial sites. The cyclo-hexene ring has a distorted half-boat conformation. There is an intra-molecular C-H⋯O hydrogen bond.

Related literature

For related structures, see: Murugavel et al. (2001 ▶); Ma et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Sn(CH3)3(C7H9O2)]

M = 288.93

Monoclinic,

a = 11.3022 (15) Å

b = 9.8469 (14) Å

c = 12.1468 (18) Å

β = 112.148 (2)°

V = 1252.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.01 mm−1

T = 298 K

0.45 × 0.36 × 0.33 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.464, T max = 0.556

6095 measured reflections

2193 independent reflections

1669 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.08

2193 reflections

118 parameters

H-atom parameters constrained

Δρmax = 1.53 e Å−3

Δρmin = −0.49 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054403/bx2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054403/bx2254Isup2.hkl

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

[Sn(CH3)3(C7H9O2)]	F(000) = 576
Mr = 288.93	Dx = 1.533 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2901 reflections
a = 11.3022 (15) Å	θ = 2.8–25.7°
b = 9.8469 (14) Å	µ = 2.01 mm−1
c = 12.1468 (18) Å	T = 298 K
β = 112.148 (2)°	Block, colourless
V = 1252.1 (3) Å3	0.45 × 0.36 × 0.33 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1669 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.464, Tmax = 0.556	k = −10→11
6095 measured reflections	l = −14→9

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0436P)2 + 2.3141P] where P = (Fo2 + 2Fc2)/3
2193 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 1.53 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.17568 (3)	0.09824 (4)	0.23917 (3)	0.04584 (17)
O1	0.3014 (4)	0.2882 (4)	0.2205 (5)	0.0699 (12)
O2	0.4496 (4)	0.4411 (4)	0.2415 (4)	0.0652 (12)
C1	0.4091 (6)	0.3183 (6)	0.2231 (6)	0.0574 (15)
C2	0.4961 (6)	0.2138 (7)	0.2052 (7)	0.0694 (18)
H2	0.4529	0.1255	0.1915	0.083*
C3	0.5310 (8)	0.2458 (9)	0.1026 (8)	0.101 (3)
H3A	0.4539	0.2451	0.0313	0.121*
H3B	0.5654	0.3373	0.1125	0.121*
C4	0.6246 (10)	0.1532 (11)	0.0847 (10)	0.118 (3)
H4	0.6277	0.1437	0.0097	0.142*
C5	0.7028 (9)	0.0848 (9)	0.1741 (10)	0.098 (3)
H5	0.7612	0.0275	0.1603	0.118*
C6	0.7047 (9)	0.0922 (9)	0.2906 (10)	0.104 (3)
H6A	0.7920	0.1077	0.3449	0.125*
H6B	0.6781	0.0051	0.3106	0.125*
C7	0.6205 (7)	0.2020 (9)	0.3105 (8)	0.091 (2)
H7A	0.6032	0.1806	0.3809	0.109*
H7B	0.6650	0.2883	0.3236	0.109*
C8	0.1852 (7)	0.0177 (7)	0.0817 (6)	0.0684 (18)
H8A	0.2669	−0.0244	0.0994	0.103*
H8B	0.1742	0.0896	0.0253	0.103*
H8C	0.1189	−0.0486	0.0489	0.103*
C9	0.0327 (6)	0.2468 (6)	0.2198 (7)	0.072 (2)
H9A	0.0032	0.2384	0.2840	0.109*
H9B	−0.0375	0.2333	0.1456	0.109*
H9C	0.0679	0.3358	0.2212	0.109*
C10	0.3183 (7)	0.0735 (7)	0.4101 (6)	0.075 (2)
H10A	0.3965	0.0455	0.4031	0.113*
H10B	0.2917	0.0057	0.4528	0.113*
H10C	0.3315	0.1581	0.4523	0.113*

	U11	U22	U33	U12	U13	U23
Sn1	0.0474 (3)	0.0394 (2)	0.0517 (3)	0.00229 (17)	0.01983 (19)	0.00063 (18)
O1	0.065 (3)	0.049 (2)	0.105 (4)	−0.003 (2)	0.043 (3)	−0.001 (3)
O2	0.063 (3)	0.046 (2)	0.102 (4)	−0.0029 (19)	0.048 (3)	−0.007 (2)
C1	0.063 (4)	0.046 (3)	0.070 (4)	0.004 (3)	0.032 (3)	0.003 (3)
C2	0.066 (4)	0.053 (4)	0.098 (5)	0.005 (3)	0.041 (4)	−0.009 (4)
C3	0.114 (6)	0.101 (6)	0.110 (7)	0.027 (5)	0.068 (6)	−0.007 (5)
C4	0.129 (8)	0.132 (8)	0.110 (8)	0.048 (7)	0.065 (7)	−0.001 (7)
C5	0.090 (6)	0.092 (6)	0.123 (8)	0.026 (5)	0.054 (6)	−0.011 (6)
C6	0.097 (6)	0.092 (6)	0.121 (8)	0.033 (5)	0.039 (6)	0.008 (6)
C7	0.085 (5)	0.087 (6)	0.103 (6)	0.021 (5)	0.040 (5)	0.005 (5)
C8	0.077 (4)	0.073 (4)	0.059 (4)	−0.006 (4)	0.030 (4)	−0.006 (4)
C9	0.061 (4)	0.049 (3)	0.111 (6)	0.012 (3)	0.036 (4)	0.016 (4)
C10	0.079 (5)	0.080 (5)	0.054 (4)	0.002 (4)	0.009 (4)	0.006 (4)

Sn1—C10	2.108 (7)	C5—C6	1.408 (14)
Sn1—C8	2.110 (6)	C5—H5	0.9300
Sn1—C9	2.126 (6)	C6—C7	1.519 (11)
Sn1—O2i	2.169 (4)	C6—H6A	0.9700
Sn1—O1	2.411 (4)	C6—H6B	0.9700
O1—C1	1.241 (7)	C7—H7A	0.9700
O2—C1	1.282 (7)	C7—H7B	0.9700
O2—Sn1ii	2.169 (4)	C8—H8A	0.9600
C1—C2	1.495 (8)	C8—H8B	0.9600
C2—C3	1.475 (10)	C8—H8C	0.9600
C2—C7	1.506 (10)	C9—H9A	0.9600
C2—H2	0.9800	C9—H9B	0.9600
C3—C4	1.474 (11)	C9—H9C	0.9600
C3—H3A	0.9700	C10—H10A	0.9600
C3—H3B	0.9700	C10—H10B	0.9600
C4—C5	1.300 (13)	C10—H10C	0.9600
C4—H4	0.9300
C10—Sn1—C8	124.6 (3)	C6—C5—H5	118.0
C10—Sn1—C9	117.1 (3)	C5—C6—C7	115.0 (8)
C8—Sn1—C9	117.0 (3)	C5—C6—H6A	108.5
C10—Sn1—O2i	95.7 (2)	C7—C6—H6A	108.5
C8—Sn1—O2i	95.1 (2)	C5—C6—H6B	108.5
C9—Sn1—O2i	90.2 (2)	C7—C6—H6B	108.5
C10—Sn1—O1	85.6 (2)	H6A—C6—H6B	107.5
C8—Sn1—O1	88.4 (2)	C2—C7—C6	111.1 (7)
C9—Sn1—O1	84.6 (2)	C2—C7—H7A	109.4
O2i—Sn1—O1	174.62 (14)	C6—C7—H7A	109.4
C1—O1—Sn1	142.2 (4)	C2—C7—H7B	109.4
C1—O2—Sn1ii	119.1 (4)	C6—C7—H7B	109.4
O1—C1—O2	120.8 (5)	H7A—C7—H7B	108.0
O1—C1—C2	121.6 (6)	Sn1—C8—H8A	109.5
O2—C1—C2	117.6 (5)	Sn1—C8—H8B	109.5
C3—C2—C1	112.1 (6)	H8A—C8—H8B	109.5
C3—C2—C7	105.8 (6)	Sn1—C8—H8C	109.5
C1—C2—C7	112.6 (6)	H8A—C8—H8C	109.5
C3—C2—H2	108.8	H8B—C8—H8C	109.5
C1—C2—H2	108.8	Sn1—C9—H9A	109.5
C7—C2—H2	108.8	Sn1—C9—H9B	109.5
C4—C3—C2	115.3 (8)	H9A—C9—H9B	109.5
C4—C3—H3A	108.4	Sn1—C9—H9C	109.5
C2—C3—H3A	108.4	H9A—C9—H9C	109.5
C4—C3—H3B	108.4	H9B—C9—H9C	109.5
C2—C3—H3B	108.4	Sn1—C10—H10A	109.5
H3A—C3—H3B	107.5	Sn1—C10—H10B	109.5
C5—C4—C3	119.8 (9)	H10A—C10—H10B	109.5
C5—C4—H4	120.1	Sn1—C10—H10C	109.5
C3—C4—H4	120.1	H10A—C10—H10C	109.5
C4—C5—C6	124.1 (8)	H10B—C10—H10C	109.5
C4—C5—H5	118.0

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2	0.97	2.60	2.926 (10)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O2	0.97	2.60	2.926 (10)	100