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Acta Cryst. (2009). E65, m1676    [ doi:10.1107/S1600536809049381 ]

Dichloridobis(4-chlorobenzyl)(4,4'-dimethyl-2,2'-bipyridine-[kappa]2N,N')tin(IV)

T. C. Keng, K. M. Lo and S. W. Ng

Abstract top

The SnIV atom in the title compound, [Sn(C7H6Cl)2Cl2(C12H12N2)], is coordinated by the bidentate N-heterocycle molecule, two chlorobenzyl anions and two Cl- anions in a distorted trans-C2SnCl2N2 octahedral geometry [C-Sn-C = 178.4 (1)°]. In the molecular structure, the two benzene rings are oriented at a dihedral angle of 39.62 (17)°.

Related literature top

For the synthesis of bis(4-chlorobenzyl)tin dichloride, see: Sisido et al. (1961). For the 1,10-phenanthroline adduct, see: Tan et al. (2009).

Experimental top

Di(4-chlorobenzyl)tin dichloride was synthesized by the reaction of 4-chlorobenzyl chloride and metallic tin (Sisido et al.). The diorganotin compound (0.44 g, 1 mmol) and 4,4'-dimethyl-2,2'-bipyridine (0.18 g, 1 mmol) was heated in chloroform (30 ml) for 1 h. Faint-yellow crystals separated upon slow evaporation of the solvent.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

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 SnCl2(C10H12N2)(C7H6Cl)2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Dichloridobis(4-chlorobenzyl)(4,4'-dimethyl-2,2'-bipyridine- κ2N,N')tin(IV) top
Crystal data top
[Sn(C7H6Cl)2Cl2(C12H12N2)]F(000) = 1248
Mr = 624.96Dx = 1.497 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6177 reflections
a = 11.4035 (6) Åθ = 2.4–28.3°
b = 14.6804 (8) ŵ = 1.32 mm−1
c = 16.9270 (9) ÅT = 293 K
β = 101.9182 (9)°Block, pale yellow
V = 2772.6 (3) Å30.30 × 0.28 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		6263 independent reflections
Radiation source: fine-focus sealed tube4883 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.692, Tmax = 0.778k = −19→18
15766 measured reflectionsl = −21→17
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0523P)2 + 1.1119P]
where P = (Fo2 + 2Fc2)/3
6263 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.78 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
Crystal data top
[Sn(C7H6Cl)2Cl2(C12H12N2)]V = 2772.6 (3) Å3
Mr = 624.96Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.4035 (6) ŵ = 1.32 mm−1
b = 14.6804 (8) ÅT = 293 K
c = 16.9270 (9) Å0.30 × 0.28 × 0.20 mm
β = 101.9182 (9)°
Data collection top
Bruker SMART APEX
diffractometer		6263 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4883 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.778Rint = 0.017
15766 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.78 e Å−3
S = 1.00Δρmin = −0.49 e Å−3
6263 reflectionsAbsolute structure: ?
300 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.278374 (15)0.231209 (14)0.536683 (11)0.05372 (8)
Cl10.06174 (7)0.19394 (9)0.52457 (7)0.0993 (3)
Cl20.28579 (8)0.31620 (8)0.40783 (5)0.0894 (3)
Cl30.35723 (13)−0.23372 (9)0.67467 (9)0.1119 (4)
Cl40.68248 (17)0.53534 (12)0.79043 (9)0.1696 (8)
N10.4862 (2)0.24492 (17)0.57811 (15)0.0558 (5)
N20.34094 (19)0.16803 (15)0.66356 (12)0.0513 (5)
C10.3049 (3)0.1063 (2)0.47620 (17)0.0686 (8)
H1A0.23820.09850.43090.082*
H1B0.37680.11270.45450.082*
C20.3163 (3)0.0226 (2)0.52556 (17)0.0606 (7)
C30.2208 (3)−0.0357 (2)0.5251 (2)0.0721 (8)
H30.1468−0.02190.49260.087*
C40.2322 (3)−0.1133 (3)0.5713 (2)0.0788 (9)
H40.1670−0.15180.56960.095*
C50.3412 (3)−0.1333 (2)0.6199 (2)0.0726 (8)
C60.4370 (3)−0.0777 (2)0.62247 (19)0.0680 (8)
H60.5105−0.09200.65550.082*
C70.4249 (3)−0.0004 (2)0.57607 (18)0.0639 (7)
H70.49070.03770.57840.077*
C80.2463 (3)0.3566 (2)0.5963 (2)0.0728 (8)
H8A0.20640.39880.55530.087*
H8B0.19110.34340.63130.087*
C90.3519 (3)0.4035 (2)0.64484 (19)0.0664 (8)
C100.3852 (3)0.3904 (2)0.7278 (2)0.0735 (8)
H100.33890.35290.75350.088*
C110.4853 (4)0.4318 (3)0.7727 (2)0.0858 (11)
H110.50590.42300.82820.103*
C120.5538 (4)0.4856 (3)0.7352 (2)0.0943 (12)
C130.5227 (4)0.5011 (3)0.6537 (2)0.0985 (13)
H130.56910.53940.62880.118*
C140.4235 (4)0.4599 (2)0.6093 (2)0.0797 (9)
H140.40350.46990.55390.096*
C150.5562 (3)0.2800 (2)0.5314 (2)0.0705 (9)
H150.52270.29340.47780.085*
C160.6750 (3)0.2967 (3)0.5597 (2)0.0813 (10)
H160.72130.32050.52540.098*
C170.7262 (3)0.2785 (3)0.6385 (3)0.0825 (10)
C180.6537 (3)0.2412 (2)0.6866 (2)0.0689 (8)
H180.68580.22770.74040.083*
C190.5348 (2)0.22410 (18)0.65515 (16)0.0516 (6)
C200.8561 (4)0.2981 (5)0.6727 (3)0.139 (2)
H20A0.89840.30370.62950.209*
H20B0.88990.24920.70770.209*
H20C0.86290.35400.70280.209*
C210.4549 (2)0.17973 (18)0.70150 (15)0.0528 (6)
C220.4934 (3)0.1484 (2)0.77971 (18)0.0733 (9)
H220.57250.15790.80600.088*
C230.4162 (4)0.1035 (3)0.81914 (19)0.0831 (10)
C240.3023 (3)0.0899 (2)0.7781 (2)0.0772 (9)
H240.24830.05800.80190.093*
C250.2669 (3)0.1234 (2)0.70125 (18)0.0632 (7)
H250.18790.11470.67440.076*
C260.4588 (5)0.0702 (4)0.9050 (2)0.138 (2)
H26A0.45590.00490.90600.206*
H26B0.40790.09460.93850.206*
H26C0.53970.09020.92490.206*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04228 (11)0.06803 (14)0.04599 (12)0.00021 (8)−0.00217 (8)0.00089 (8)
Cl10.0438 (4)0.1234 (8)0.1241 (8)−0.0074 (4)0.0018 (4)−0.0088 (7)
Cl20.0821 (6)0.1201 (8)0.0552 (5)−0.0123 (5)−0.0105 (4)0.0282 (5)
Cl30.1097 (9)0.1036 (8)0.1256 (10)−0.0010 (6)0.0316 (8)0.0320 (7)
Cl40.2037 (16)0.1603 (14)0.1127 (10)−0.1049 (13)−0.0418 (10)0.0234 (9)
N10.0450 (12)0.0726 (15)0.0471 (13)−0.0018 (10)0.0032 (10)0.0021 (10)
N20.0498 (11)0.0597 (13)0.0425 (11)−0.0029 (9)0.0052 (9)−0.0037 (10)
C10.0699 (18)0.087 (2)0.0462 (15)0.0005 (16)0.0043 (13)−0.0122 (15)
C20.0583 (15)0.0721 (19)0.0503 (15)0.0011 (13)0.0084 (12)−0.0151 (13)
C30.0534 (17)0.088 (2)0.0686 (19)−0.0050 (15)−0.0018 (14)−0.0151 (18)
C40.0645 (19)0.085 (2)0.086 (2)−0.0156 (17)0.0133 (17)−0.012 (2)
C50.074 (2)0.076 (2)0.071 (2)−0.0009 (16)0.0231 (16)−0.0028 (17)
C60.0580 (17)0.082 (2)0.0625 (18)0.0071 (15)0.0097 (14)−0.0047 (16)
C70.0520 (15)0.079 (2)0.0605 (17)−0.0022 (13)0.0127 (13)−0.0135 (15)
C80.0664 (18)0.072 (2)0.077 (2)0.0131 (15)0.0066 (16)−0.0032 (17)
C90.078 (2)0.0556 (16)0.0646 (18)0.0083 (14)0.0125 (15)−0.0035 (14)
C100.094 (2)0.0649 (19)0.0637 (19)0.0016 (17)0.0216 (17)−0.0017 (15)
C110.123 (3)0.074 (2)0.0553 (18)−0.008 (2)0.0051 (19)0.0007 (16)
C120.123 (3)0.076 (2)0.073 (2)−0.032 (2)−0.005 (2)0.0002 (19)
C130.133 (4)0.079 (2)0.079 (2)−0.038 (2)0.012 (2)0.009 (2)
C140.104 (3)0.069 (2)0.0620 (19)−0.0090 (19)0.0083 (18)0.0058 (16)
C150.0569 (17)0.100 (3)0.0549 (17)−0.0075 (15)0.0106 (14)0.0061 (16)
C160.0580 (18)0.111 (3)0.079 (2)−0.0180 (18)0.0228 (17)−0.002 (2)
C170.0478 (17)0.110 (3)0.085 (3)−0.0116 (16)0.0041 (16)−0.013 (2)
C180.0496 (16)0.091 (2)0.0591 (18)−0.0032 (14)−0.0051 (13)−0.0041 (16)
C190.0464 (13)0.0581 (15)0.0456 (14)0.0008 (11)−0.0012 (11)−0.0047 (11)
C200.054 (2)0.222 (6)0.133 (4)−0.037 (3)−0.001 (2)−0.004 (4)
C210.0567 (14)0.0535 (15)0.0434 (13)−0.0033 (11)−0.0006 (11)−0.0032 (11)
C220.080 (2)0.076 (2)0.0520 (17)−0.0178 (16)−0.0151 (14)0.0107 (15)
C230.112 (3)0.079 (2)0.0510 (17)−0.026 (2)−0.0015 (18)0.0113 (16)
C240.101 (3)0.074 (2)0.0589 (18)−0.0274 (18)0.0211 (18)−0.0006 (16)
C250.0643 (17)0.0681 (18)0.0575 (17)−0.0124 (14)0.0131 (13)−0.0064 (14)
C260.184 (5)0.145 (5)0.066 (2)−0.062 (4)−0.016 (3)0.040 (3)
Geometric parameters (Å, °) top
Sn1—C12.151 (3)C10—H100.9300
Sn1—C82.166 (3)C11—C121.357 (5)
Sn1—N22.313 (2)C11—H110.9300
Sn1—N12.337 (2)C12—C131.371 (5)
Sn1—Cl12.4970 (9)C13—C141.363 (5)
Sn1—Cl22.5293 (8)C13—H130.9300
Cl3—C51.731 (4)C14—H140.9300
Cl4—C121.730 (4)C15—C161.363 (5)
N1—C191.343 (4)C15—H150.9300
N1—C151.337 (4)C16—C171.366 (5)
N2—C251.331 (4)C16—H160.9300
N2—C211.336 (3)C17—C181.388 (5)
C1—C21.476 (5)C17—C201.502 (5)
C1—H1A0.9700C18—C191.374 (4)
C1—H1B0.9700C18—H180.9300
C2—C31.384 (4)C19—C211.472 (4)
C2—C71.394 (4)C20—H20A0.9600
C3—C41.372 (5)C20—H20B0.9600
C3—H30.9300C20—H20C0.9600
C4—C51.374 (5)C21—C221.384 (4)
C4—H40.9300C22—C231.378 (5)
C5—C61.358 (5)C22—H220.9300
C6—C71.371 (5)C23—C241.356 (5)
C6—H60.9300C23—C261.515 (5)
C7—H70.9300C24—C251.371 (4)
C8—C91.480 (5)C24—H240.9300
C8—H8A0.9700C25—H250.9300
C8—H8B0.9700C26—H26A0.9600
C9—C101.391 (5)C26—H26B0.9600
C9—C141.385 (5)C26—H26C0.9600
C10—C111.375 (5)
C1—Sn1—C8178.42 (12)C9—C10—H10119.4
C1—Sn1—N293.06 (10)C12—C11—C10119.4 (3)
C8—Sn1—N287.58 (11)C12—C11—H11120.3
C1—Sn1—N188.99 (11)C10—C11—H11120.3
C8—Sn1—N192.59 (11)C11—C12—C13120.9 (4)
N2—Sn1—N169.92 (8)C11—C12—Cl4119.9 (3)
C1—Sn1—Cl190.48 (9)C13—C12—Cl4119.2 (3)
C8—Sn1—Cl188.01 (9)C14—C13—C12119.5 (4)
N2—Sn1—Cl195.66 (6)C14—C13—H13120.2
N1—Sn1—Cl1165.52 (7)C12—C13—H13120.2
C1—Sn1—Cl288.68 (9)C13—C14—C9121.5 (3)
C8—Sn1—Cl291.21 (10)C13—C14—H14119.2
N2—Sn1—Cl2160.01 (6)C9—C14—H14119.2
N1—Sn1—Cl290.22 (6)N1—C15—C16122.2 (3)
Cl1—Sn1—Cl2104.24 (4)N1—C15—H15118.9
C19—N1—C15119.0 (3)C16—C15—H15118.9
C19—N1—Sn1117.50 (18)C15—C16—C17120.1 (3)
C15—N1—Sn1123.2 (2)C15—C16—H16120.0
C25—N2—C21118.9 (2)C17—C16—H16120.0
C25—N2—Sn1122.54 (19)C16—C17—C18117.6 (3)
C21—N2—Sn1118.53 (17)C16—C17—C20121.8 (4)
C2—C1—Sn1116.38 (19)C18—C17—C20120.5 (4)
C2—C1—H1A108.2C19—C18—C17120.3 (3)
Sn1—C1—H1A108.2C19—C18—H18119.9
C2—C1—H1B108.2C17—C18—H18119.9
Sn1—C1—H1B108.2N1—C19—C18120.8 (3)
H1A—C1—H1B107.3N1—C19—C21116.2 (2)
C3—C2—C7116.8 (3)C18—C19—C21123.0 (3)
C3—C2—C1122.4 (3)C17—C20—H20A109.5
C7—C2—C1120.8 (3)C17—C20—H20B109.5
C4—C3—C2122.0 (3)H20A—C20—H20B109.5
C4—C3—H3119.0C17—C20—H20C109.5
C2—C3—H3119.0H20A—C20—H20C109.5
C3—C4—C5119.1 (3)H20B—C20—H20C109.5
C3—C4—H4120.4N2—C21—C22120.1 (3)
C5—C4—H4120.4N2—C21—C19116.6 (2)
C6—C5—C4120.9 (3)C22—C21—C19123.2 (3)
C6—C5—Cl3120.0 (3)C23—C22—C21120.9 (3)
C4—C5—Cl3119.1 (3)C23—C22—H22119.5
C5—C6—C7119.6 (3)C21—C22—H22119.5
C5—C6—H6120.2C24—C23—C22117.5 (3)
C7—C6—H6120.2C24—C23—C26121.9 (4)
C6—C7—C2121.6 (3)C22—C23—C26120.6 (4)
C6—C7—H7119.2C23—C24—C25119.8 (3)
C2—C7—H7119.2C23—C24—H24120.1
C9—C8—Sn1117.3 (2)C25—C24—H24120.1
C9—C8—H8A108.0N2—C25—C24122.7 (3)
Sn1—C8—H8A108.0N2—C25—H25118.7
C9—C8—H8B108.0C24—C25—H25118.7
Sn1—C8—H8B108.0C23—C26—H26A109.5
H8A—C8—H8B107.2C23—C26—H26B109.5
C10—C9—C14117.3 (3)H26A—C26—H26B109.5
C10—C9—C8121.2 (3)C23—C26—H26C109.5
C14—C9—C8121.4 (3)H26A—C26—H26C109.5
C11—C10—C9121.3 (3)H26B—C26—H26C109.5
C11—C10—H10119.4
C1—Sn1—N1—C1582.9 (3)Sn1—C8—C9—C10−95.9 (3)
N2—Sn1—N1—C15176.5 (3)C14—C9—C10—C11−0.1 (5)
Cl1—Sn1—N1—C15170.9 (2)C8—C9—C10—C11178.0 (3)
Cl2—Sn1—N1—C15−5.8 (3)C9—C10—C11—C12−0.8 (6)
C1—Sn1—N1—C19−103.4 (2)C10—C11—C12—C131.7 (7)
C8—Sn1—N1—C1976.7 (2)C10—C11—C12—Cl4−178.0 (3)
N2—Sn1—N1—C19−9.79 (19)C11—C12—C13—C14−1.8 (7)
Cl1—Sn1—N1—C19−15.4 (4)Cl4—C12—C13—C14178.0 (4)
Cl2—Sn1—N1—C19167.9 (2)C12—C13—C14—C90.9 (7)
C1—Sn1—N2—C25−86.3 (2)C10—C9—C14—C130.0 (6)
C8—Sn1—N2—C2592.2 (2)C8—C9—C14—C13−178.1 (4)
N1—Sn1—N2—C25−174.1 (2)C19—N1—C15—C16−1.1 (5)
Cl1—Sn1—N2—C254.5 (2)Sn1—N1—C15—C16172.5 (3)
Cl2—Sn1—N2—C25179.13 (18)N1—C15—C16—C17−0.7 (6)
C1—Sn1—N2—C2196.2 (2)C15—C16—C17—C181.4 (6)
C8—Sn1—N2—C21−85.3 (2)C15—C16—C17—C20−178.4 (4)
N1—Sn1—N2—C218.36 (19)C16—C17—C18—C19−0.3 (6)
Cl1—Sn1—N2—C21−173.05 (19)C20—C17—C18—C19179.5 (4)
Cl2—Sn1—N2—C211.6 (3)C15—N1—C19—C182.2 (4)
C8—Sn1—C1—C2−97 (5)Sn1—N1—C19—C18−171.8 (2)
N2—Sn1—C1—C216.6 (2)C15—N1—C19—C21−175.8 (3)
N1—Sn1—C1—C286.5 (2)Sn1—N1—C19—C2110.3 (3)
Cl1—Sn1—C1—C2−79.0 (2)C17—C18—C19—N1−1.5 (5)
Cl2—Sn1—C1—C2176.7 (2)C17—C18—C19—C21176.3 (3)
Sn1—C1—C2—C397.9 (3)C25—N2—C21—C22−2.2 (4)
Sn1—C1—C2—C7−81.2 (3)Sn1—N2—C21—C22175.5 (2)
C7—C2—C3—C4−0.8 (5)C25—N2—C21—C19176.1 (2)
C1—C2—C3—C4−179.9 (3)Sn1—N2—C21—C19−6.3 (3)
C2—C3—C4—C50.6 (5)N1—C19—C21—N2−2.7 (4)
C3—C4—C5—C6−0.3 (5)C18—C19—C21—N2179.4 (3)
C3—C4—C5—Cl3−177.1 (3)N1—C19—C21—C22175.5 (3)
C4—C5—C6—C70.3 (5)C18—C19—C21—C22−2.4 (5)
Cl3—C5—C6—C7177.0 (2)N2—C21—C22—C231.2 (5)
C5—C6—C7—C2−0.5 (5)C19—C21—C22—C23−176.9 (3)
C3—C2—C7—C60.7 (4)C21—C22—C23—C241.0 (6)
C1—C2—C7—C6179.9 (3)C21—C22—C23—C26−179.4 (4)
N2—Sn1—C8—C965.4 (3)C22—C23—C24—C25−2.2 (6)
N1—Sn1—C8—C9−4.4 (3)C26—C23—C24—C25178.2 (4)
Cl1—Sn1—C8—C9161.1 (3)C21—N2—C25—C240.9 (4)
Cl2—Sn1—C8—C9−94.6 (3)Sn1—N2—C25—C24−176.6 (2)
Sn1—C8—C9—C1482.1 (4)C23—C24—C25—N21.4 (5)
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
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