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Acta Cryst. (2009). E65, m490    [ doi:10.1107/S1600536809012240 ]

Tricyclohexyl(2,3-dibromo-3-phenylpropionato-[kappa]O)tin(IV)

P. Y. Thong, K. M. Lo and S. W. Ng

Abstract top

Tricyclohexyltin cinnamate reacts with 4,4-dimethylaminopyridine hydrobromide perbromide to form the title compound, [Sn(C6H11)3(C9H7Br2O2)], which exists as a monomeric molecule with the Sn atom in a distorted tetrahedral C3O coordination geometry.

Related literature top

For reviews of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Tricyclohexyltin chloride (1.93 g, 5 mmol) was reacted with cinnamic acid (0.74 g, 5 mmol) in ethanol (100 ml) under reflux for 2 h. The product, tricyclohexyltin cinnamate, was collected upon removal of the solvent. The organotin compound (1 g, 2 mmol) and 4,4-dimethylaminopyridine hydrobromide perbromide (0.73 g, 2 mmol) were heated in 1:1 ethanol:chloroform (100 ml) for 1 h. Slow evaporation of the filtrate gave colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The large peak/hole is in the vicinity (about 1 Å) of the C21 atom.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Sn(C6H11)3(C9H7Br2O2) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Tricyclohexyl(2,3-dibromo-3-phenylpropionato-κO)tin(IV) top
Crystal data top
[Sn(C6H11)3(C9H7Br2O2)]F(000) = 1352
Mr = 675.10Dx = 1.626 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7301 reflections
a = 21.2359 (3) Åθ = 2.5–28.2°
b = 9.0837 (1) ŵ = 3.85 mm−1
c = 15.0550 (2) ÅT = 118 K
β = 108.287 (1)°Block, colorless
V = 2757.45 (6) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		6325 independent reflections
Radiation source: fine-focus sealed tube5007 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −27→27
Tmin = 0.392, Tmax = 0.700k = −11→11
21967 measured reflectionsl = −18→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0318P)2 + 6.5266P]
where P = (Fo2 + 2Fc2)/3
6325 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 1.63 e Å−3
0 restraintsΔρmin = −1.13 e Å−3
Crystal data top
[Sn(C6H11)3(C9H7Br2O2)]V = 2757.45 (6) Å3
Mr = 675.10Z = 4
Monoclinic, P21/cMo Kα radiation
a = 21.2359 (3) ŵ = 3.85 mm−1
b = 9.0837 (1) ÅT = 118 K
c = 15.0550 (2) Å0.30 × 0.20 × 0.10 mm
β = 108.287 (1)°
Data collection top
Bruker SMART APEX
diffractometer		6325 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5007 reflections with I > 2σ(I)
Tmin = 0.392, Tmax = 0.700Rint = 0.034
21967 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.083Δρmax = 1.63 e Å−3
S = 1.04Δρmin = −1.13 e Å−3
6325 reflectionsAbsolute structure: ?
289 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.213693 (12)0.54260 (3)0.484115 (16)0.02051 (7)
Br10.43779 (2)0.37225 (5)0.44008 (3)0.03484 (11)
Br20.258387 (19)0.05999 (4)0.32990 (3)0.03129 (10)
O10.26589 (15)0.4358 (3)0.4077 (2)0.0387 (7)
O20.31430 (15)0.2973 (3)0.5299 (2)0.0452 (8)
C10.15692 (17)0.6666 (4)0.3632 (2)0.0220 (7)
H10.18950.70610.33360.026*
C20.12163 (19)0.7996 (4)0.3873 (3)0.0264 (8)
H2A0.08940.76590.41830.032*
H2B0.15450.86360.43180.032*
C30.08542 (19)0.8880 (4)0.3002 (3)0.0279 (8)
H3A0.06040.96900.31770.033*
H3B0.11830.93240.27390.033*
C40.03775 (18)0.7926 (4)0.2262 (3)0.0275 (8)
H4A0.01780.85190.16910.033*
H4B0.00150.75870.24940.033*
C50.07263 (19)0.6598 (4)0.2018 (2)0.0282 (8)
H5A0.10510.69330.17110.034*
H5B0.03960.59640.15710.034*
C60.1087 (2)0.5702 (4)0.2895 (3)0.0276 (8)
H6A0.07570.52700.31610.033*
H6B0.13330.48850.27210.033*
C70.16265 (18)0.3824 (4)0.5421 (2)0.0232 (7)
H70.19460.35020.60330.028*
C80.1404 (2)0.2437 (4)0.4836 (3)0.0293 (8)
H8A0.10930.27090.42170.035*
H8B0.17940.19540.47350.035*
C90.1064 (2)0.1361 (4)0.5322 (3)0.0338 (9)
H9A0.08990.05020.49090.041*
H9B0.13920.10000.59050.041*
C100.04875 (19)0.2078 (4)0.5554 (3)0.0289 (8)
H10A0.03000.13710.59030.035*
H10B0.01350.23340.49670.035*
C110.0710 (2)0.3462 (4)0.6139 (3)0.0307 (9)
H11A0.10280.31930.67540.037*
H11B0.03220.39390.62480.037*
C120.10404 (19)0.4543 (4)0.5642 (3)0.0265 (8)
H12A0.07110.48790.50530.032*
H12B0.11980.54150.60440.032*
C130.28327 (18)0.6755 (4)0.5863 (2)0.0229 (7)
H130.31580.60800.62990.028*
C140.2482 (2)0.7634 (4)0.6445 (3)0.0302 (8)
H14A0.21350.82650.60240.036*
H14B0.22630.69430.67640.036*
C150.2972 (2)0.8594 (5)0.7173 (3)0.0399 (10)
H15A0.27290.91920.75090.048*
H15B0.32900.79570.76370.048*
C160.3352 (2)0.9610 (5)0.6714 (3)0.0399 (10)
H16A0.30391.03140.62990.048*
H16B0.36821.01820.72030.048*
C170.3701 (2)0.8748 (5)0.6152 (3)0.0350 (9)
H17A0.40470.81210.65790.042*
H17B0.39230.94400.58390.042*
C180.3220 (2)0.7777 (5)0.5415 (3)0.0333 (9)
H18A0.34720.71800.50920.040*
H18B0.29060.84070.49440.040*
C190.3064 (2)0.3375 (5)0.4512 (4)0.0428 (11)
C200.3465 (4)0.2732 (7)0.3902 (6)0.086 (2)
H200.32540.31140.32540.103*
C210.3511 (4)0.1324 (10)0.3833 (6)0.103 (3)
H210.36610.09570.44930.123*
C220.3980 (3)0.0619 (6)0.3377 (4)0.0589 (15)
C230.4391 (3)−0.0514 (6)0.3837 (4)0.0600 (15)
H230.4393−0.07950.44450.072*
C240.4791 (3)−0.1224 (6)0.3434 (3)0.0489 (12)
H240.5066−0.20060.37570.059*
C250.4800 (2)−0.0820 (5)0.2563 (3)0.0362 (10)
H250.5080−0.13280.22820.043*
C260.4408 (2)0.0312 (5)0.2089 (3)0.0345 (9)
H260.44200.05890.14860.041*
C270.3996 (2)0.1048 (5)0.2490 (3)0.0436 (11)
H270.37270.18370.21670.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02214 (13)0.02028 (12)0.02122 (12)0.00165 (10)0.00982 (9)0.00100 (10)
Br10.0356 (2)0.0413 (2)0.0301 (2)−0.01657 (18)0.01398 (17)−0.01001 (18)
Br20.0250 (2)0.0332 (2)0.0360 (2)−0.00672 (16)0.01009 (16)−0.00529 (17)
O10.0474 (18)0.0441 (18)0.0341 (16)0.0140 (15)0.0263 (14)0.0022 (14)
O20.0359 (17)0.0354 (17)0.062 (2)0.0099 (14)0.0122 (15)0.0110 (16)
C10.0203 (17)0.0223 (18)0.0237 (18)0.0007 (14)0.0074 (14)0.0011 (14)
C20.028 (2)0.0254 (19)0.0253 (19)0.0027 (16)0.0082 (15)−0.0006 (15)
C30.031 (2)0.0236 (19)0.028 (2)0.0009 (16)0.0076 (16)−0.0007 (16)
C40.0256 (19)0.032 (2)0.0227 (18)−0.0020 (16)0.0040 (15)0.0050 (16)
C50.032 (2)0.029 (2)0.0205 (18)−0.0075 (16)0.0043 (15)−0.0031 (15)
C60.035 (2)0.0218 (19)0.0246 (19)−0.0027 (16)0.0071 (16)−0.0005 (15)
C70.0257 (19)0.0220 (18)0.0228 (18)−0.0010 (15)0.0089 (15)0.0011 (14)
C80.034 (2)0.0249 (19)0.034 (2)−0.0017 (16)0.0180 (17)−0.0064 (16)
C90.042 (2)0.0209 (19)0.045 (2)−0.0004 (17)0.023 (2)−0.0037 (17)
C100.032 (2)0.0251 (19)0.033 (2)−0.0035 (16)0.0154 (17)−0.0015 (16)
C110.038 (2)0.028 (2)0.034 (2)−0.0040 (17)0.0220 (18)−0.0049 (17)
C120.031 (2)0.0194 (18)0.035 (2)−0.0029 (16)0.0189 (17)−0.0048 (16)
C130.0227 (18)0.0240 (18)0.0206 (17)0.0039 (15)0.0047 (14)0.0033 (14)
C140.033 (2)0.032 (2)0.029 (2)−0.0006 (17)0.0143 (17)−0.0025 (17)
C150.049 (3)0.043 (3)0.032 (2)−0.010 (2)0.019 (2)−0.013 (2)
C160.047 (3)0.030 (2)0.042 (2)−0.010 (2)0.012 (2)−0.0065 (19)
C170.037 (2)0.036 (2)0.032 (2)−0.0117 (19)0.0109 (18)0.0017 (18)
C180.035 (2)0.039 (2)0.029 (2)−0.0110 (18)0.0153 (17)−0.0035 (18)
C190.043 (3)0.036 (2)0.058 (3)0.008 (2)0.028 (2)−0.002 (2)
C200.089 (5)0.067 (4)0.129 (6)0.024 (4)0.073 (5)−0.014 (4)
C210.088 (5)0.115 (6)0.129 (7)−0.017 (5)0.069 (5)−0.069 (6)
C220.073 (4)0.064 (4)0.059 (3)−0.002 (3)0.048 (3)−0.026 (3)
C230.096 (5)0.057 (3)0.039 (3)−0.001 (3)0.039 (3)−0.004 (3)
C240.058 (3)0.049 (3)0.036 (3)0.005 (2)0.008 (2)−0.004 (2)
C250.028 (2)0.043 (2)0.041 (2)−0.0025 (18)0.0155 (18)−0.017 (2)
C260.045 (2)0.035 (2)0.030 (2)−0.0115 (19)0.0210 (19)−0.0097 (18)
C270.048 (3)0.033 (2)0.050 (3)0.006 (2)0.016 (2)−0.012 (2)
Geometric parameters (Å, °) top
Sn1—O12.072 (3)C11—H11A0.9900
Sn1—C132.141 (4)C11—H11B0.9900
Sn1—C72.157 (3)C12—H12A0.9900
Sn1—C12.158 (3)C12—H12B0.9900
Br1—C202.054 (8)C13—C181.530 (5)
Br2—C211.990 (7)C13—C141.539 (5)
O1—C191.271 (5)C13—H131.0000
O2—C191.201 (6)C14—C151.526 (6)
C1—C61.528 (5)C14—H14A0.9900
C1—C21.525 (5)C14—H14B0.9900
C1—H11.0000C15—C161.526 (6)
C2—C31.525 (5)C15—H15A0.9900
C2—H2A0.9900C15—H15B0.9900
C2—H2B0.9900C16—C171.507 (6)
C3—C41.520 (5)C16—H16A0.9900
C3—H3A0.9900C16—H16B0.9900
C3—H3B0.9900C17—C181.530 (6)
C4—C51.519 (5)C17—H17A0.9900
C4—H4A0.9900C17—H17B0.9900
C4—H4B0.9900C18—H18A0.9900
C5—C61.536 (5)C18—H18B0.9900
C5—H5A0.9900C19—C201.548 (7)
C5—H5B0.9900C20—C211.290 (10)
C6—H6A0.9900C20—H201.0000
C6—H6B0.9900C21—C221.517 (7)
C7—C121.531 (5)C21—H211.0000
C7—C81.525 (5)C22—C231.387 (8)
C7—H71.0000C22—C271.402 (7)
C8—C91.531 (5)C23—C241.351 (7)
C8—H8A0.9900C23—H230.9500
C8—H8B0.9900C24—C251.369 (6)
C9—C101.521 (5)C24—H240.9500
C9—H9A0.9900C25—C261.374 (6)
C9—H9B0.9900C25—H250.9500
C10—C111.523 (5)C26—C271.381 (6)
C10—H10A0.9900C26—H260.9500
C10—H10B0.9900C27—H270.9500
C11—C121.531 (5)
O1—Sn1—C13107.13 (13)C7—C12—H12A109.4
O1—Sn1—C7109.48 (13)C11—C12—H12A109.4
C13—Sn1—C7114.25 (13)C7—C12—H12B109.4
O1—Sn1—C191.76 (12)C11—C12—H12B109.4
C13—Sn1—C1112.88 (13)H12A—C12—H12B108.0
C7—Sn1—C1118.36 (14)C18—C13—C14111.1 (3)
C19—O1—Sn1115.9 (3)C18—C13—Sn1111.7 (2)
C6—C1—C2111.1 (3)C14—C13—Sn1110.7 (2)
C6—C1—Sn1112.5 (2)C18—C13—H13107.7
C2—C1—Sn1113.5 (2)C14—C13—H13107.7
C6—C1—H1106.4Sn1—C13—H13107.7
C2—C1—H1106.4C15—C14—C13111.2 (3)
Sn1—C1—H1106.4C15—C14—H14A109.4
C3—C2—C1111.4 (3)C13—C14—H14A109.4
C3—C2—H2A109.3C15—C14—H14B109.4
C1—C2—H2A109.3C13—C14—H14B109.4
C3—C2—H2B109.3H14A—C14—H14B108.0
C1—C2—H2B109.3C16—C15—C14111.0 (3)
H2A—C2—H2B108.0C16—C15—H15A109.4
C4—C3—C2111.7 (3)C14—C15—H15A109.4
C4—C3—H3A109.3C16—C15—H15B109.4
C2—C3—H3A109.3C14—C15—H15B109.4
C4—C3—H3B109.3H15A—C15—H15B108.0
C2—C3—H3B109.3C17—C16—C15111.2 (4)
H3A—C3—H3B107.9C17—C16—H16A109.4
C3—C4—C5111.5 (3)C15—C16—H16A109.4
C3—C4—H4A109.3C17—C16—H16B109.4
C5—C4—H4A109.3C15—C16—H16B109.4
C3—C4—H4B109.3H16A—C16—H16B108.0
C5—C4—H4B109.3C16—C17—C18111.9 (4)
H4A—C4—H4B108.0C16—C17—H17A109.2
C4—C5—C6111.3 (3)C18—C17—H17A109.2
C4—C5—H5A109.4C16—C17—H17B109.2
C6—C5—H5A109.4C18—C17—H17B109.2
C4—C5—H5B109.4H17A—C17—H17B107.9
C6—C5—H5B109.4C17—C18—C13111.0 (3)
H5A—C5—H5B108.0C17—C18—H18A109.4
C1—C6—C5111.1 (3)C13—C18—H18A109.4
C1—C6—H6A109.4C17—C18—H18B109.4
C5—C6—H6A109.4C13—C18—H18B109.4
C1—C6—H6B109.4H18A—C18—H18B108.0
C5—C6—H6B109.4O2—C19—O1125.8 (4)
H6A—C6—H6B108.0O2—C19—C20122.6 (5)
C12—C7—C8110.6 (3)O1—C19—C20111.6 (5)
C12—C7—Sn1110.2 (2)C21—C20—C19119.5 (6)
C8—C7—Sn1115.3 (2)C21—C20—Br1112.1 (6)
C12—C7—H7106.7C19—C20—Br1104.4 (4)
C8—C7—H7106.7C21—C20—H20106.7
Sn1—C7—H7106.7C19—C20—H20106.7
C9—C8—C7111.0 (3)Br1—C20—H20106.7
C9—C8—H8A109.4C20—C21—C22122.2 (7)
C7—C8—H8A109.4C20—C21—Br2105.6 (6)
C9—C8—H8B109.4C22—C21—Br2112.6 (4)
C7—C8—H8B109.4C20—C21—H21105.0
H8A—C8—H8B108.0C22—C21—H21105.0
C10—C9—C8111.8 (3)Br2—C21—H21105.0
C10—C9—H9A109.3C23—C22—C27118.8 (4)
C8—C9—H9A109.3C23—C22—C21119.1 (6)
C10—C9—H9B109.3C27—C22—C21122.0 (6)
C8—C9—H9B109.3C24—C23—C22121.1 (5)
H9A—C9—H9B107.9C24—C23—H23119.5
C9—C10—C11111.1 (3)C22—C23—H23119.5
C9—C10—H10A109.4C23—C24—C25120.1 (5)
C11—C10—H10A109.4C23—C24—H24119.9
C9—C10—H10B109.4C25—C24—H24119.9
C11—C10—H10B109.4C24—C25—C26120.6 (4)
H10A—C10—H10B108.0C24—C25—H25119.7
C10—C11—C12110.7 (3)C26—C25—H25119.7
C10—C11—H11A109.5C25—C26—C27120.0 (4)
C12—C11—H11A109.5C25—C26—H26120.0
C10—C11—H11B109.5C27—C26—H26120.0
C12—C11—H11B109.5C26—C27—C22119.4 (5)
H11A—C11—H11B108.1C26—C27—H27120.3
C7—C12—C11111.1 (3)C22—C27—H27120.3
C13—Sn1—O1—C1969.2 (3)O1—Sn1—C13—C14178.1 (2)
C7—Sn1—O1—C19−55.2 (3)C7—Sn1—C13—C14−60.5 (3)
C1—Sn1—O1—C19−176.2 (3)C1—Sn1—C13—C1478.6 (3)
O1—Sn1—C1—C669.1 (3)C18—C13—C14—C15−54.9 (4)
C13—Sn1—C1—C6178.5 (2)Sn1—C13—C14—C15−179.7 (3)
C7—Sn1—C1—C6−44.2 (3)C13—C14—C15—C1655.5 (5)
O1—Sn1—C1—C2−163.7 (3)C14—C15—C16—C17−56.1 (5)
C13—Sn1—C1—C2−54.2 (3)C15—C16—C17—C1856.1 (5)
C7—Sn1—C1—C283.0 (3)C16—C17—C18—C13−55.3 (5)
C6—C1—C2—C3−55.1 (4)C14—C13—C18—C1754.2 (4)
Sn1—C1—C2—C3176.9 (2)Sn1—C13—C18—C17178.4 (3)
C1—C2—C3—C454.8 (4)Sn1—O1—C19—O23.9 (7)
C2—C3—C4—C5−54.7 (4)Sn1—O1—C19—C20−175.7 (4)
C3—C4—C5—C654.9 (4)O2—C19—C20—C2149.4 (11)
C2—C1—C6—C555.4 (4)O1—C19—C20—C21−131.0 (8)
Sn1—C1—C6—C5−176.1 (2)O2—C19—C20—Br1−76.9 (6)
C4—C5—C6—C1−55.3 (4)O1—C19—C20—Br1102.7 (5)
O1—Sn1—C7—C12−157.5 (2)C19—C20—C21—C22−170.2 (6)
C13—Sn1—C7—C1282.4 (3)Br1—C20—C21—C22−47.6 (11)
C1—Sn1—C7—C12−54.3 (3)C19—C20—C21—Br259.5 (9)
O1—Sn1—C7—C8−31.4 (3)Br1—C20—C21—Br2−177.9 (3)
C13—Sn1—C7—C8−151.5 (3)C20—C21—C22—C23131.4 (9)
C1—Sn1—C7—C871.8 (3)Br2—C21—C22—C23−101.3 (7)
C12—C7—C8—C9−55.5 (4)C20—C21—C22—C27−50.6 (11)
Sn1—C7—C8—C9178.6 (3)Br2—C21—C22—C2776.7 (7)
C7—C8—C9—C1055.3 (5)C27—C22—C23—C24−1.7 (9)
C8—C9—C10—C11−55.4 (5)C21—C22—C23—C24176.4 (6)
C9—C10—C11—C1255.8 (5)C22—C23—C24—C250.7 (9)
C8—C7—C12—C1156.6 (4)C23—C24—C25—C260.4 (8)
Sn1—C7—C12—C11−174.7 (3)C24—C25—C26—C27−0.5 (7)
C10—C11—C12—C7−56.7 (4)C25—C26—C27—C22−0.5 (7)
O1—Sn1—C13—C1853.7 (3)C23—C22—C27—C261.5 (8)
C7—Sn1—C13—C18175.1 (3)C21—C22—C27—C26−176.5 (5)
C1—Sn1—C13—C18−45.8 (3)
Acknowledgements top

We thank the University of Malaya (FS339/2008 A) for supporting this study.

references
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