catena-Poly[[trimethyl­tin(IV)]-μ-cyclo­hex-3-ene-1-carboxyl­ato]

Ren, Y.; Zhang, R.; Shi, Y.

doi:10.1107/S1600536809054403

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m92

doi:10.1107/S1600536809054403

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catena-Poly[[trimethyltin(IV)]-μ-cyclohex-3-ene-1-carboxylato]

Yun Ren,^a Rufen Zhang ^b ^* and Yang Shi ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bDepartment of Chemistry, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: macl@lcu.edu.cn

(Received 3 December 2009; accepted 17 December 2009; online 24 December 2009)

The title compound, [Sn(CH₃)₃(C₇H₉O₂)]_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 carboxylate O atoms in the axial and the three methyl groups in equatorial sites. The cyclohexene ring has a distorted half-boat conformation. There is an intramolecular 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_r = 288.93
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.101
S = 1.08
2193 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 1.53 e Å⁻³
Δρ_min = −0.49 e Å⁻³

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

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.

Supporting information

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

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

checkCIF report

Comment top

Organotin complexes are attracting more and more attention because of their considerable structural diversity and interesting topologies (Murugavel et al. 2001). Herein, we report the crystal structure of the title compound. The title compound, which is shown in Fig.1 forms an infinite zigzag one-dimensional polymeric chain structure.The Sn atom is in a slightly distorted trigonal-bipyramidal coordination environment with two carboxylate O atoms in the axial sites and three methyl groups in equatorial site.The Sn—O, Sn—C bond lenghts and the O—Sn···O bond angles are close to the reported organotin compounds (Ma et al. 2006). The cyclohexene ring is in a distorted half-boat conformation, the ring-puckering parameters (Cremer & Pople, 1975) are q₂ = 0.380 (1) Å , q₃ = -0.314 (1) Å , Q = 0.492 (9) ° and ϕ₂ = 165.1 (2)°. There is an intramolecular C—H···O hydrogen bond (H3B—O2 2.60 , C3—O2 2.926 (10) Å, C3—H3B···O2 100°).

Related literature top

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

Experimental top

The reaction was carried out under nitrogen atmosphere. 3-cyclohexene-1-carboxylic acid (1 mmol) and sodium ethoxide (1 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 to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from ether to yield colorless blocks of the title compound (yield 86% m.p.448 K). Anal. Calcd (%) for C₁₀H₁₈O₂Sn₁ (Mr = 288.93): C, 41.57; H, 6.28; Found (%): C, 41.76; H, 6.01.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Part of the polymericstructure and the atom-numbering scheme of the title compound. Displacementellipsoids are shown at the 30% probability level and H atoms have been omitted for clarity.
	Fig. 2. Part of the structure of (I) showing the one-dimensional chain along the b axis[symmetry codes: (i) 1/2-x,-1/2+y, 1/2-z; (ii) 1/2-x,1/2+y,1/2-z].

catena-Poly[[trimethyltin(IV)]-µ-cyclohex-3-ene-1-carboxylato] top

Crystal data top

[Sn(CH₃)₃(C₇H₉O₂)]	F(000) = 576
M_r = 288.93	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0436P)² + 2.3141P] where P = (F_o² + 2F_c²)/3
2193 reflections	(Δ/σ)_max = 0.001
118 parameters	Δρ_max = 1.53 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₇H₉O₂)]	V = 1252.1 (3) Å³
M_r = 288.93	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3022 (15) Å	µ = 2.01 mm⁻¹
b = 9.8469 (14) Å	T = 298 K
c = 12.1468 (18) Å	0.45 × 0.36 × 0.33 mm
β = 112.148 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2193 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1669 reflections with I > 2σ(I)
T_min = 0.464, T_max = 0.556	R_int = 0.033
6095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 1.53 e Å⁻³
2193 reflections	Δρ_min = −0.49 e Å⁻³
118 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₇H₉O₂)]
M_r	288.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.3022 (15), 9.8469 (14), 12.1468 (18)
β (°)	112.148 (2)
V (Å³)	1252.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.45 × 0.36 × 0.33

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.464, 0.556
No. of measured, independent and observed [I > 2σ(I)] reflections	6095, 2193, 1669
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.101, 1.08
No. of reflections	2193
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.53, −0.49

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (20971096) for financial support.

References

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