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Acta Cryst. (2009). E65, m717    [ doi:10.1107/S1600536809019795 ]

Dichloridobis(4-chlorobenzyl-[kappa]C)(1,10-phenanthroline-[kappa]2N,N')tin(IV)

C. L. Tan, K. M. Lo and S. W. Ng

Abstract top

In the crystal structure of the title compound, [Sn(C7H6Cl)2Cl2(C12H8N2)], the SnIV atom is chelated by the N-heterocycle and the metal atom exists in a trans-C2SnCl2N2 distorted octahedral coordination environment.

Related literature top

Several diorganotin dichloride adducts of 2,2'-bipyridine have been reported. For the diethyltin dichloride, dibutyltin dichoride and dibenzyltin dichloride adducts; see Chadha et al. (1980); Gill et al.(1999); Tiekink et al. (2000). For the structure of di(4-chlorobenzyltin) dichloride, see: Kuang & Feng (2000). For the direct synthesis of di(chlorobenzyl)tin dichlorides, see: Sisido et al. (1961).

Experimental top

Di(p-chlorobenzyl)tin dichloride was synthesized by the reaction of p-chlorobenzyl chloride and metallic tin (Sisido et al., 1961). The reactant (0.5 g, 1.1 mmol) and 1,10-phenanthroline (0.2 g, 1.1 mmol) were heated in chloroform (50 ml) for 1 hour. Faint-yellow crystals separated from the cool solution after a day.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 70% displacement probability ellipsoids. Hydrogen atoms are drawn as spheres of arbitrary radius.
Dichloridobis(4-chlorobenzyl-κC)(1,10-phenanthroline- κ2N,N')tin(IV) top
Crystal data top
[Sn(C7H6Cl)2Cl2(C12H8N2)]F(000) = 1232
Mr = 620.93Dx = 1.656 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8381 reflections
a = 8.9252 (1) Åθ = 2.3–28.2°
b = 17.9987 (3) ŵ = 1.47 mm−1
c = 15.6862 (3) ÅT = 119 K
β = 98.686 (1)°Prism, yellow
V = 2490.96 (7) Å30.40 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		5681 independent reflections
Radiation source: fine-focus sealed tube4826 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.590, Tmax = 0.867k = −22→23
16905 measured reflectionsl = −20→20
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0286P)2 + 1.4291P]
where P = (Fo2 + 2Fc2)/3
5681 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
[Sn(C7H6Cl)2Cl2(C12H8N2)]V = 2490.96 (7) Å3
Mr = 620.93Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9252 (1) ŵ = 1.47 mm−1
b = 17.9987 (3) ÅT = 119 K
c = 15.6862 (3) Å0.40 × 0.10 × 0.10 mm
β = 98.686 (1)°
Data collection top
Bruker SMART APEX
diffractometer		5681 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4826 reflections with I > 2σ(I)
Tmin = 0.590, Tmax = 0.867Rint = 0.021
16905 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.53 e Å−3
S = 1.05Δρmin = −0.44 e Å−3
5681 reflectionsAbsolute structure: ?
298 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.668417 (16)0.554696 (8)0.795225 (9)0.02121 (5)
Cl10.84702 (8)0.57955 (4)0.35794 (4)0.04106 (15)
Cl21.35725 (11)0.75339 (6)0.97376 (6)0.0765 (3)
Cl30.42667 (7)0.52254 (3)0.85279 (4)0.03635 (14)
Cl40.82575 (7)0.43941 (3)0.81282 (4)0.03295 (13)
N10.5902 (2)0.67771 (10)0.75699 (12)0.0231 (4)
N20.8592 (2)0.61534 (10)0.73338 (12)0.0232 (4)
C10.7565 (3)0.59581 (14)0.92228 (15)0.0302 (5)
H1A0.68110.63040.94050.036*
H1B0.76630.55330.96280.036*
C20.9049 (3)0.63463 (13)0.93108 (14)0.0291 (5)
C31.0409 (3)0.59536 (13)0.94752 (15)0.0313 (5)
H3A1.03820.54270.95030.038*
C41.1800 (3)0.63119 (16)0.95997 (17)0.0399 (6)
H4A1.27160.60370.97250.048*
C51.1823 (4)0.70741 (17)0.95385 (17)0.0444 (7)
C61.0518 (4)0.74826 (15)0.93470 (18)0.0499 (8)
H6A1.05600.80070.92920.060*
C70.9140 (3)0.71175 (14)0.92356 (16)0.0399 (6)
H7A0.82320.73980.91050.048*
C80.5528 (2)0.51792 (13)0.67136 (15)0.0259 (5)
H8A0.53660.46360.67460.031*
H8B0.45160.54160.66150.031*
C90.6284 (2)0.53300 (12)0.59490 (14)0.0236 (4)
C100.7343 (3)0.48429 (13)0.56968 (15)0.0281 (5)
H10A0.76040.44060.60250.034*
C110.8025 (3)0.49820 (13)0.49766 (15)0.0294 (5)
H11A0.87380.46410.48080.035*
C120.7655 (3)0.56232 (13)0.45046 (15)0.0290 (5)
C130.6620 (3)0.61251 (13)0.47410 (15)0.0301 (5)
H13A0.63780.65660.44160.036*
C140.5942 (3)0.59752 (13)0.54598 (15)0.0281 (5)
H14A0.52280.63180.56250.034*
C150.6868 (2)0.71888 (11)0.71740 (14)0.0221 (4)
C160.4601 (3)0.70774 (13)0.77128 (15)0.0277 (5)
H16A0.39330.67900.79980.033*
C170.4182 (3)0.78056 (13)0.74554 (17)0.0334 (5)
H17A0.32490.80070.75690.040*
C180.5130 (3)0.82184 (13)0.70422 (16)0.0325 (5)
H18A0.48460.87070.68520.039*
C190.6528 (3)0.79239 (12)0.68953 (15)0.0281 (5)
C200.7614 (3)0.83310 (13)0.64909 (15)0.0346 (6)
H20A0.73880.88250.62990.041*
C210.8942 (3)0.80256 (14)0.63798 (15)0.0337 (6)
H21A0.96430.83080.61140.040*
C220.9325 (3)0.72786 (13)0.66552 (14)0.0282 (5)
C231.0714 (3)0.69379 (16)0.65643 (16)0.0348 (6)
H23A1.14430.71990.62970.042*
C241.1010 (3)0.62301 (15)0.68614 (16)0.0356 (6)
H24A1.19480.59980.68100.043*
C250.9913 (3)0.58531 (14)0.72420 (15)0.0288 (5)
H25A1.01240.53610.74430.035*
C260.8288 (2)0.68613 (12)0.70487 (14)0.0231 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02126 (8)0.01781 (8)0.02478 (8)0.00048 (6)0.00414 (6)−0.00034 (6)
Cl10.0462 (4)0.0487 (4)0.0299 (3)−0.0001 (3)0.0111 (3)0.0010 (3)
Cl20.0833 (6)0.0975 (7)0.0515 (5)−0.0638 (6)0.0192 (5)−0.0244 (5)
Cl30.0361 (3)0.0285 (3)0.0493 (4)−0.0040 (2)0.0220 (3)−0.0024 (3)
Cl40.0322 (3)0.0230 (3)0.0424 (3)0.0073 (2)0.0017 (3)0.0020 (2)
N10.0221 (9)0.0201 (9)0.0271 (10)−0.0018 (7)0.0033 (8)−0.0027 (7)
N20.0204 (9)0.0261 (10)0.0226 (9)−0.0026 (7)0.0019 (7)−0.0039 (7)
C10.0345 (13)0.0315 (12)0.0244 (11)0.0055 (10)0.0041 (10)−0.0019 (10)
C20.0420 (14)0.0268 (12)0.0179 (11)−0.0005 (10)0.0033 (10)−0.0027 (9)
C30.0388 (13)0.0265 (12)0.0287 (12)−0.0032 (10)0.0053 (10)−0.0051 (10)
C40.0391 (14)0.0490 (16)0.0327 (14)−0.0081 (12)0.0083 (12)−0.0129 (12)
C50.0597 (19)0.0497 (17)0.0246 (13)−0.0293 (15)0.0090 (13)−0.0113 (12)
C60.087 (2)0.0287 (14)0.0304 (14)−0.0172 (15)−0.0030 (15)−0.0025 (11)
C70.0597 (18)0.0270 (13)0.0296 (13)0.0023 (12)−0.0038 (12)−0.0051 (10)
C80.0195 (10)0.0280 (12)0.0296 (12)−0.0026 (9)0.0018 (9)−0.0041 (9)
C90.0186 (10)0.0264 (11)0.0237 (11)−0.0024 (8)−0.0037 (9)−0.0047 (9)
C100.0253 (11)0.0274 (12)0.0298 (12)0.0006 (9)−0.0015 (10)−0.0026 (9)
C110.0244 (11)0.0325 (12)0.0304 (12)0.0031 (9)0.0015 (10)−0.0047 (10)
C120.0266 (11)0.0369 (13)0.0227 (11)−0.0023 (10)0.0004 (9)−0.0024 (10)
C130.0303 (12)0.0295 (12)0.0275 (12)0.0033 (10)−0.0052 (10)0.0006 (10)
C140.0263 (11)0.0272 (12)0.0290 (12)0.0049 (9)−0.0019 (9)−0.0043 (9)
C150.0269 (11)0.0198 (10)0.0186 (10)−0.0044 (8)0.0004 (8)−0.0030 (8)
C160.0256 (11)0.0242 (11)0.0336 (13)0.0000 (9)0.0053 (10)−0.0026 (9)
C170.0349 (13)0.0254 (12)0.0396 (14)0.0061 (10)0.0042 (11)−0.0042 (10)
C180.0448 (14)0.0188 (11)0.0326 (13)0.0041 (10)0.0016 (11)0.0003 (9)
C190.0387 (13)0.0200 (11)0.0247 (11)−0.0039 (9)0.0018 (10)−0.0028 (9)
C200.0540 (16)0.0229 (12)0.0271 (12)−0.0084 (11)0.0072 (11)0.0010 (9)
C210.0447 (15)0.0321 (13)0.0248 (12)−0.0179 (11)0.0072 (11)−0.0028 (10)
C220.0311 (12)0.0347 (13)0.0186 (11)−0.0118 (10)0.0030 (9)−0.0041 (9)
C230.0262 (12)0.0531 (16)0.0260 (12)−0.0147 (11)0.0066 (10)−0.0045 (11)
C240.0233 (11)0.0501 (16)0.0341 (13)−0.0029 (11)0.0070 (10)−0.0070 (12)
C250.0233 (11)0.0351 (12)0.0280 (12)0.0001 (10)0.0036 (9)−0.0055 (10)
C260.0250 (11)0.0245 (11)0.0190 (10)−0.0059 (9)0.0011 (8)−0.0045 (8)
Geometric parameters (Å, °) top
Sn1—C12.160 (2)C9—C141.400 (3)
Sn1—C82.162 (2)C10—C111.385 (3)
Sn1—N12.3712 (18)C10—H10A0.9500
Sn1—N22.3515 (18)C11—C121.384 (3)
Sn1—Cl32.5287 (6)C11—H11A0.9500
Sn1—Cl42.4973 (6)C12—C131.382 (3)
Cl1—C121.747 (2)C13—C141.385 (3)
Cl2—C51.753 (3)C13—H13A0.9500
N1—C161.330 (3)C14—H14A0.9500
N1—C151.356 (3)C15—C191.412 (3)
N2—C251.325 (3)C15—C261.438 (3)
N2—C261.364 (3)C16—C171.405 (3)
C1—C21.486 (3)C16—H16A0.9500
C1—H1A0.9900C17—C181.361 (4)
C1—H1B0.9900C17—H17A0.9500
C2—C31.394 (3)C18—C191.406 (3)
C2—C71.397 (3)C18—H18A0.9500
C3—C41.386 (4)C19—C201.437 (3)
C3—H3A0.9500C20—C211.342 (4)
C4—C51.376 (4)C20—H20A0.9500
C4—H4A0.9500C21—C221.437 (4)
C5—C61.372 (4)C21—H21A0.9500
C6—C71.382 (4)C22—C261.405 (3)
C6—H6A0.9500C22—C231.410 (3)
C7—H7A0.9500C23—C241.368 (4)
C8—C91.487 (3)C23—H23A0.9500
C8—H8A0.9900C24—C251.397 (3)
C8—H8B0.9900C24—H24A0.9500
C9—C101.390 (3)C25—H25A0.9500
C1—Sn1—C8172.84 (8)C14—C9—C8120.4 (2)
C8—Sn1—N292.78 (7)C11—C10—C9121.3 (2)
C1—Sn1—N292.08 (8)C11—C10—H10A119.3
C8—Sn1—N188.64 (8)C9—C10—H10A119.3
C1—Sn1—N188.03 (8)C10—C11—C12119.3 (2)
N2—Sn1—N170.49 (6)C10—C11—H11A120.4
C8—Sn1—Cl491.67 (6)C12—C11—H11A120.4
C1—Sn1—Cl493.58 (7)C13—C12—C11121.1 (2)
N2—Sn1—Cl490.07 (5)C13—C12—Cl1119.07 (19)
N1—Sn1—Cl4160.55 (5)C11—C12—Cl1119.81 (18)
C8—Sn1—Cl386.19 (6)C14—C13—C12118.9 (2)
C1—Sn1—Cl387.72 (7)C14—C13—H13A120.6
N2—Sn1—Cl3164.47 (5)C12—C13—H13A120.6
N1—Sn1—Cl393.99 (5)C13—C14—C9121.5 (2)
Cl4—Sn1—Cl3105.44 (2)C13—C14—H14A119.3
C16—N1—C15119.11 (19)C9—C14—H14A119.3
C16—N1—Sn1124.61 (15)N1—C15—C19122.1 (2)
C15—N1—Sn1116.28 (14)N1—C15—C26118.23 (19)
C25—N2—C26118.79 (19)C19—C15—C26119.6 (2)
C25—N2—Sn1124.56 (16)N1—C16—C17122.1 (2)
C26—N2—Sn1116.65 (14)N1—C16—H16A118.9
C2—C1—Sn1116.24 (15)C17—C16—H16A118.9
C2—C1—H1A108.2C18—C17—C16119.3 (2)
Sn1—C1—H1A108.2C18—C17—H17A120.4
C2—C1—H1B108.2C16—C17—H17A120.4
Sn1—C1—H1B108.2C17—C18—C19120.2 (2)
H1A—C1—H1B107.4C17—C18—H18A119.9
C3—C2—C7117.4 (2)C19—C18—H18A119.9
C3—C2—C1121.2 (2)C18—C19—C15117.2 (2)
C7—C2—C1121.4 (2)C18—C19—C20123.7 (2)
C4—C3—C2121.7 (2)C15—C19—C20119.1 (2)
C4—C3—H3A119.1C21—C20—C19121.1 (2)
C2—C3—H3A119.1C21—C20—H20A119.4
C5—C4—C3118.5 (3)C19—C20—H20A119.4
C5—C4—H4A120.8C20—C21—C22121.2 (2)
C3—C4—H4A120.8C20—C21—H21A119.4
C6—C5—C4121.9 (3)C22—C21—H21A119.4
C6—C5—Cl2119.3 (2)C26—C22—C23117.4 (2)
C4—C5—Cl2118.7 (3)C26—C22—C21119.3 (2)
C5—C6—C7118.9 (3)C23—C22—C21123.3 (2)
C5—C6—H6A120.6C24—C23—C22119.9 (2)
C7—C6—H6A120.6C24—C23—H23A120.1
C6—C7—C2121.6 (3)C22—C23—H23A120.1
C6—C7—H7A119.2C23—C24—C25119.1 (2)
C2—C7—H7A119.2C23—C24—H24A120.5
C9—C8—Sn1117.12 (14)C25—C24—H24A120.5
C9—C8—H8A108.0N2—C25—C24122.7 (2)
Sn1—C8—H8A108.0N2—C25—H25A118.6
C9—C8—H8B108.0C24—C25—H25A118.6
Sn1—C8—H8B108.0N2—C26—C22122.1 (2)
H8A—C8—H8B107.3N2—C26—C15118.27 (19)
C10—C9—C14118.0 (2)C22—C26—C15119.6 (2)
C10—C9—C8121.7 (2)
C8—Sn1—N1—C1688.53 (19)C10—C11—C12—C130.0 (4)
C1—Sn1—N1—C16−85.14 (19)C10—C11—C12—Cl1−178.41 (18)
N2—Sn1—N1—C16−178.0 (2)C11—C12—C13—C14−0.4 (3)
Cl4—Sn1—N1—C16179.68 (13)Cl1—C12—C13—C14178.03 (18)
Cl3—Sn1—N1—C162.44 (18)C12—C13—C14—C90.1 (3)
C8—Sn1—N1—C15−91.05 (16)C10—C9—C14—C130.6 (3)
C1—Sn1—N1—C1595.29 (16)C8—C9—C14—C13−179.4 (2)
N2—Sn1—N1—C152.38 (14)C16—N1—C15—C19−1.0 (3)
Cl4—Sn1—N1—C150.1 (3)Sn1—N1—C15—C19178.60 (16)
Cl3—Sn1—N1—C15−177.13 (15)C16—N1—C15—C26178.2 (2)
C8—Sn1—N2—C25−94.31 (18)Sn1—N1—C15—C26−2.2 (2)
C1—Sn1—N2—C2590.94 (18)C15—N1—C16—C170.9 (3)
N1—Sn1—N2—C25178.12 (19)Sn1—N1—C16—C17−178.64 (17)
Cl4—Sn1—N2—C25−2.64 (17)N1—C16—C17—C180.4 (4)
Cl3—Sn1—N2—C25179.92 (14)C16—C17—C18—C19−1.6 (4)
C8—Sn1—N2—C2685.20 (16)C17—C18—C19—C151.5 (3)
C1—Sn1—N2—C26−89.54 (16)C17—C18—C19—C20−177.8 (2)
N1—Sn1—N2—C26−2.37 (14)N1—C15—C19—C18−0.2 (3)
Cl4—Sn1—N2—C26176.87 (15)C26—C15—C19—C18−179.4 (2)
Cl3—Sn1—N2—C26−0.6 (3)N1—C15—C19—C20179.1 (2)
N2—Sn1—C1—C2−8.28 (18)C26—C15—C19—C200.0 (3)
N1—Sn1—C1—C2−78.67 (18)C18—C19—C20—C21178.9 (2)
Cl4—Sn1—C1—C281.92 (17)C15—C19—C20—C21−0.4 (4)
Cl3—Sn1—C1—C2−172.74 (18)C19—C20—C21—C220.4 (4)
Sn1—C1—C2—C3−86.5 (2)C20—C21—C22—C260.0 (3)
Sn1—C1—C2—C793.7 (2)C20—C21—C22—C23−179.0 (2)
C7—C2—C3—C42.9 (4)C26—C22—C23—C24−0.5 (3)
C1—C2—C3—C4−176.9 (2)C21—C22—C23—C24178.4 (2)
C2—C3—C4—C5−1.5 (4)C22—C23—C24—C250.8 (4)
C3—C4—C5—C6−0.9 (4)C26—N2—C25—C24−0.3 (3)
C3—C4—C5—Cl2177.49 (19)Sn1—N2—C25—C24179.23 (17)
C4—C5—C6—C71.8 (4)C23—C24—C25—N2−0.4 (4)
Cl2—C5—C6—C7−176.7 (2)C25—N2—C26—C220.5 (3)
C5—C6—C7—C2−0.2 (4)Sn1—N2—C26—C22−179.00 (16)
C3—C2—C7—C6−2.1 (4)C25—N2—C26—C15−178.26 (19)
C1—C2—C7—C6177.7 (2)Sn1—N2—C26—C152.2 (2)
N2—Sn1—C8—C95.87 (17)C23—C22—C26—N2−0.1 (3)
N1—Sn1—C8—C976.26 (17)C21—C22—C26—N2−179.2 (2)
Cl4—Sn1—C8—C9−84.29 (17)C23—C22—C26—C15178.7 (2)
Cl3—Sn1—C8—C9170.35 (17)C21—C22—C26—C15−0.4 (3)
Sn1—C8—C9—C1086.7 (2)N1—C15—C26—N20.0 (3)
Sn1—C8—C9—C14−93.2 (2)C19—C15—C26—N2179.24 (19)
C14—C9—C10—C11−1.0 (3)N1—C15—C26—C22−178.8 (2)
C8—C9—C10—C11179.0 (2)C19—C15—C26—C220.4 (3)
C9—C10—C11—C120.7 (3)
Table 1
Selected geometric parameters (Å, °) top
Sn1—C12.160 (2)Sn1—N22.3515 (18)
Sn1—C82.162 (2)Sn1—Cl32.5287 (6)
Sn1—N12.3712 (18)Sn1—Cl42.4973 (6)
C1—Sn1—C8172.84 (8)
Acknowledgements top

We thank the University of Malaya (RG020/09AFR) for supporting this study.

references
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