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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m304.
Published online 2010 February 17. doi:  10.1107/S1600536810005672
PMCID: PMC2983632

Dichloridobis(4-methyl­benz­yl)(1,10-phenanthroline-κ2 N,N′)tin(IV)

Abstract

The tin(IV) atom in the title compound, [Sn(C8H9)2Cl2(C12H8N2)], is chelated by the N-heterocycle and bonded to two C atoms and two chloride ions in an SnC2Cl2N2 octa­hedral coordination environment with the C atoms trans to each other. The dihedral angles between the heterocycle ring system and the benzene rings of the 4-methyl­benzyl groups are 21.20 (12) and 28.71 (11)°.

Related literature

For the crystal structure of the 1,10-phenanthroline adduct with di(4-chloro­benz­yl)tin dichloride, see: Tan et al. (2009 [triangle]). For the direct synthesis of substituted dibenzyl­tin dichlorides, see: Sisido et al. (1961 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m304-scheme1.jpg

Experimental

Crystal data

  • [Sn(C8H9)2Cl2(C12H8N2)]
  • M r = 580.10
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m304-efi1.jpg
  • a = 15.2180 (2) Å
  • b = 10.4325 (1) Å
  • c = 17.7990 (2) Å
  • β = 115.0779 (5)°
  • V = 2559.42 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.23 mm−1
  • T = 293 K
  • 0.40 × 0.30 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.640, T max = 0.887
  • 23764 measured reflections
  • 5882 independent reflections
  • 5066 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.074
  • S = 1.05
  • 5882 reflections
  • 300 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005672/hb5335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005672/hb5335Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR and PS338/2009C) for supporting this study.

supplementary crystallographic information

Experimental

Di(p-methylbenzyl)tin dichloride was synthesized by the reaction of p-methylbenzyl chloride and metallic tin (Sisido et al., 1961). The reactant (0.45 g, 1 mmol) and 1,10-phenanthroline (0.18 g, 1 mmol) were heated in chloroform (50 ml) for 1 hour. Faint-yellow, almost colourless, blocks of (I) separated from the cool solution after a day.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.93–0.96 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C8H9)2Cl2(C12H8N2)]F(000) = 1168
Mr = 580.10Dx = 1.505 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9858 reflections
a = 15.2180 (2) Åθ = 2.3–28.3°
b = 10.4325 (1) ŵ = 1.23 mm1
c = 17.7990 (2) ÅT = 293 K
β = 115.0779 (5)°Block, colourless
V = 2559.42 (5) Å30.40 × 0.30 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer5882 independent reflections
Radiation source: fine-focus sealed tube5066 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.640, Tmax = 0.887k = −13→13
23764 measured reflectionsl = −23→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0413P)2 + 0.9608P] where P = (Fo2 + 2Fc2)/3
5882 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.68 e Å3

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

xyzUiso*/Ueq
Sn10.258495 (11)0.590677 (12)0.707814 (8)0.03991 (6)
Cl10.28464 (5)0.52229 (7)0.85189 (4)0.06375 (17)
Cl20.22061 (7)0.82753 (6)0.70201 (5)0.0763 (2)
N10.24130 (14)0.58938 (17)0.56865 (11)0.0451 (4)
N20.28083 (14)0.38087 (17)0.66953 (12)0.0450 (4)
C10.41247 (18)0.6286 (3)0.75538 (14)0.0521 (5)
H1A0.42920.69560.79690.063*
H1B0.44760.55190.78270.063*
C20.44531 (17)0.6680 (2)0.69126 (13)0.0490 (5)
C30.4806 (2)0.5793 (3)0.65313 (16)0.0568 (6)
H30.48810.49430.67060.068*
C40.5051 (2)0.6148 (3)0.58943 (18)0.0673 (7)
H40.52960.55340.56560.081*
C50.49389 (19)0.7397 (3)0.56052 (16)0.0674 (8)
C60.4612 (2)0.8295 (3)0.60007 (18)0.0650 (7)
H60.45450.91450.58290.078*
C70.43823 (19)0.7948 (2)0.66475 (16)0.0561 (6)
H70.41770.85730.69100.067*
C80.5137 (3)0.7780 (5)0.4875 (2)0.1062 (15)
H8A0.45420.80410.44250.159*
H8B0.54050.70640.47050.159*
H8C0.55900.84790.50310.159*
C90.10328 (18)0.5559 (2)0.66245 (16)0.0528 (5)
H9A0.08180.59330.70170.063*
H9B0.07060.60160.61050.063*
C100.07041 (17)0.4214 (2)0.64869 (16)0.0518 (5)
C110.0640 (2)0.3462 (3)0.71101 (17)0.0671 (7)
H110.08040.38170.76320.081*
C120.0337 (2)0.2200 (3)0.6968 (2)0.0732 (8)
H120.03060.17230.73980.088*
C130.0078 (2)0.1629 (3)0.6200 (2)0.0702 (8)
C140.01504 (19)0.2365 (3)0.55829 (18)0.0606 (6)
H14−0.00080.20050.50630.073*
C150.04530 (17)0.3623 (3)0.57233 (15)0.0532 (5)
H150.04900.40920.52930.064*
C16−0.0291 (3)0.0259 (4)0.6033 (3)0.1090 (13)
H16A−0.07680.01300.62460.164*
H16B0.0240−0.03220.63010.164*
H16C−0.05790.01030.54460.164*
C170.22739 (18)0.6918 (3)0.52146 (15)0.0587 (6)
H170.22590.77200.54370.070*
C180.2148 (2)0.6835 (4)0.43852 (18)0.0781 (9)
H180.20760.75750.40730.094*
C190.2132 (2)0.5675 (4)0.40508 (18)0.0866 (11)
H190.20320.56110.34990.104*
C200.22645 (19)0.4558 (4)0.45285 (16)0.0673 (8)
C210.24283 (16)0.4721 (2)0.53616 (13)0.0470 (5)
C220.2244 (3)0.3269 (5)0.4227 (2)0.0911 (12)
H220.21310.31460.36760.109*
C230.2380 (3)0.2258 (4)0.4710 (2)0.0895 (12)
H230.23380.14440.44840.107*
C240.25889 (18)0.2374 (3)0.5567 (2)0.0661 (8)
C250.26192 (15)0.3617 (2)0.58928 (15)0.0466 (5)
C260.2746 (2)0.1346 (3)0.6110 (3)0.0806 (10)
H260.27210.05130.59160.097*
C270.2933 (2)0.1543 (2)0.6910 (2)0.0776 (9)
H270.30370.08540.72690.093*
C280.29680 (19)0.2795 (2)0.71911 (18)0.0591 (6)
H280.31090.29290.77470.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.05738 (10)0.03106 (8)0.03553 (9)−0.00481 (6)0.02380 (7)−0.00172 (5)
Cl10.0878 (4)0.0687 (4)0.0407 (3)−0.0134 (3)0.0330 (3)0.0041 (3)
Cl20.1138 (6)0.0339 (3)0.1028 (6)0.0027 (3)0.0669 (5)−0.0032 (3)
N10.0461 (10)0.0525 (11)0.0341 (9)−0.0040 (8)0.0145 (8)0.0033 (7)
N20.0484 (10)0.0345 (8)0.0492 (10)−0.0021 (7)0.0178 (8)−0.0019 (8)
C10.0595 (14)0.0567 (13)0.0350 (11)−0.0159 (11)0.0151 (10)−0.0028 (10)
C20.0512 (12)0.0536 (13)0.0370 (10)−0.0141 (10)0.0138 (9)−0.0036 (9)
C30.0604 (15)0.0576 (15)0.0492 (13)−0.0031 (11)0.0201 (11)−0.0029 (10)
C40.0653 (16)0.086 (2)0.0521 (15)−0.0013 (14)0.0265 (13)−0.0106 (14)
C50.0528 (14)0.104 (2)0.0446 (13)−0.0111 (15)0.0199 (11)0.0084 (14)
C60.0607 (15)0.0698 (17)0.0642 (16)−0.0142 (13)0.0261 (13)0.0119 (14)
C70.0618 (14)0.0512 (14)0.0580 (14)−0.0150 (11)0.0282 (12)−0.0063 (11)
C80.085 (2)0.178 (5)0.068 (2)0.005 (3)0.0453 (18)0.036 (2)
C90.0527 (13)0.0535 (13)0.0542 (13)0.0024 (11)0.0247 (11)0.0005 (11)
C100.0438 (12)0.0594 (14)0.0518 (13)−0.0039 (10)0.0198 (10)0.0023 (10)
C110.0654 (16)0.084 (2)0.0537 (14)−0.0161 (15)0.0273 (12)0.0028 (14)
C120.0649 (16)0.083 (2)0.0739 (19)−0.0168 (15)0.0317 (14)0.0190 (16)
C130.0601 (16)0.0616 (17)0.089 (2)−0.0098 (13)0.0315 (15)0.0026 (15)
C140.0525 (13)0.0616 (15)0.0671 (16)−0.0088 (12)0.0247 (12)−0.0071 (13)
C150.0467 (12)0.0590 (14)0.0508 (13)−0.0032 (11)0.0179 (10)0.0056 (11)
C160.129 (3)0.064 (2)0.150 (4)−0.023 (2)0.075 (3)−0.001 (2)
C170.0593 (14)0.0635 (15)0.0491 (13)−0.0048 (12)0.0188 (11)0.0174 (11)
C180.0656 (17)0.115 (3)0.0493 (15)−0.0040 (17)0.0203 (13)0.0327 (17)
C190.073 (2)0.151 (4)0.0376 (14)−0.010 (2)0.0253 (13)0.0004 (18)
C200.0550 (14)0.110 (2)0.0410 (13)−0.0119 (15)0.0244 (11)−0.0197 (14)
C210.0416 (11)0.0619 (14)0.0388 (11)−0.0079 (10)0.0182 (9)−0.0116 (10)
C220.082 (2)0.134 (3)0.065 (2)−0.024 (2)0.0394 (17)−0.056 (2)
C230.081 (2)0.095 (3)0.100 (3)−0.016 (2)0.046 (2)−0.062 (2)
C240.0499 (13)0.0592 (16)0.091 (2)−0.0072 (12)0.0309 (13)−0.0364 (15)
C250.0384 (10)0.0470 (12)0.0549 (13)−0.0060 (9)0.0202 (9)−0.0162 (10)
C260.0644 (17)0.0374 (13)0.133 (3)0.0004 (12)0.0348 (19)−0.0237 (17)
C270.0646 (17)0.0312 (12)0.120 (3)0.0017 (11)0.0232 (18)0.0057 (15)
C280.0574 (14)0.0413 (12)0.0707 (16)0.0045 (11)0.0195 (12)0.0080 (11)

Geometric parameters (Å, °)

Sn1—C12.164 (2)C11—C121.382 (4)
Sn1—C92.179 (2)C11—H110.9300
Sn1—N22.3595 (18)C12—C131.387 (4)
Sn1—N12.3780 (18)C12—H120.9300
Sn1—Cl12.5256 (6)C13—C141.383 (4)
Sn1—Cl22.5295 (7)C13—C161.518 (5)
N1—C171.319 (3)C14—C151.378 (4)
N1—C211.357 (3)C14—H140.9300
N2—C281.332 (3)C15—H150.9300
N2—C251.347 (3)C16—H16A0.9600
C1—C21.485 (3)C16—H16B0.9600
C1—H1A0.9700C16—H16C0.9600
C1—H1B0.9700C17—C181.408 (4)
C2—C31.384 (4)C17—H170.9300
C2—C71.393 (3)C18—C191.345 (5)
C3—C41.386 (4)C18—H180.9300
C3—H30.9300C19—C201.406 (5)
C4—C51.384 (4)C19—H190.9300
C4—H40.9300C20—C211.406 (3)
C5—C61.385 (4)C20—C221.443 (5)
C5—C81.507 (4)C21—C251.440 (4)
C6—C71.385 (4)C22—C231.320 (6)
C6—H60.9300C22—H220.9300
C7—H70.9300C23—C241.426 (5)
C8—H8A0.9600C23—H230.9300
C8—H8B0.9600C24—C261.394 (5)
C8—H8C0.9600C24—C251.413 (3)
C9—C101.475 (3)C26—C271.345 (5)
C9—H9A0.9700C26—H260.9300
C9—H9B0.9700C27—C281.391 (4)
C10—C151.390 (4)C27—H270.9300
C10—C111.395 (4)C28—H280.9300
C1—Sn1—C9178.47 (9)C11—C10—C9122.4 (2)
C1—Sn1—N291.02 (9)C12—C11—C10121.4 (3)
C9—Sn1—N290.27 (8)C12—C11—H11119.3
C1—Sn1—N191.80 (7)C10—C11—H11119.3
C9—Sn1—N189.41 (8)C11—C12—C13121.5 (3)
N2—Sn1—N170.10 (6)C11—C12—H12119.2
C1—Sn1—Cl188.62 (6)C13—C12—H12119.2
C9—Sn1—Cl190.50 (7)C14—C13—C12117.4 (3)
N2—Sn1—Cl192.93 (5)C14—C13—C16121.0 (3)
N1—Sn1—Cl1163.03 (5)C12—C13—C16121.7 (3)
C1—Sn1—Cl291.59 (8)C13—C14—C15121.2 (3)
C9—Sn1—Cl287.42 (7)C13—C14—H14119.4
N2—Sn1—Cl2162.30 (5)C15—C14—H14119.4
N1—Sn1—Cl292.32 (5)C14—C15—C10122.1 (2)
Cl1—Sn1—Cl2104.63 (3)C14—C15—H15118.9
C17—N1—C21119.1 (2)C10—C15—H15118.9
C17—N1—Sn1125.14 (18)C13—C16—H16A109.5
C21—N1—Sn1115.77 (14)C13—C16—H16B109.5
C28—N2—C25118.8 (2)H16A—C16—H16B109.5
C28—N2—Sn1123.61 (17)C13—C16—H16C109.5
C25—N2—Sn1116.86 (15)H16A—C16—H16C109.5
C2—C1—Sn1114.29 (15)H16B—C16—H16C109.5
C2—C1—H1A108.7N1—C17—C18122.1 (3)
Sn1—C1—H1A108.7N1—C17—H17118.9
C2—C1—H1B108.7C18—C17—H17118.9
Sn1—C1—H1B108.7C19—C18—C17119.2 (3)
H1A—C1—H1B107.6C19—C18—H18120.4
C3—C2—C7117.3 (2)C17—C18—H18120.4
C3—C2—C1121.2 (2)C18—C19—C20120.5 (3)
C7—C2—C1121.4 (2)C18—C19—H19119.7
C4—C3—C2121.1 (3)C20—C19—H19119.7
C4—C3—H3119.4C21—C20—C19116.9 (3)
C2—C3—H3119.4C21—C20—C22118.1 (3)
C3—C4—C5121.5 (3)C19—C20—C22125.0 (3)
C3—C4—H4119.3N1—C21—C20122.1 (3)
C5—C4—H4119.3N1—C21—C25118.45 (19)
C4—C5—C6117.5 (2)C20—C21—C25119.4 (2)
C4—C5—C8122.1 (3)C23—C22—C20122.0 (3)
C6—C5—C8120.3 (3)C23—C22—H22119.0
C7—C6—C5121.1 (3)C20—C22—H22119.0
C7—C6—H6119.4C22—C23—C24122.1 (3)
C5—C6—H6119.4C22—C23—H23119.0
C6—C7—C2121.3 (3)C24—C23—H23119.0
C6—C7—H7119.4C26—C24—C25117.1 (3)
C2—C7—H7119.4C26—C24—C23124.8 (3)
C5—C8—H8A109.5C25—C24—C23118.1 (3)
C5—C8—H8B109.5N2—C25—C24121.8 (2)
H8A—C8—H8B109.5N2—C25—C21118.1 (2)
C5—C8—H8C109.5C24—C25—C21120.2 (2)
H8A—C8—H8C109.5C27—C26—C24120.8 (3)
H8B—C8—H8C109.5C27—C26—H26119.6
C10—C9—Sn1117.26 (17)C24—C26—H26119.6
C10—C9—H9A108.0C26—C27—C28118.9 (3)
Sn1—C9—H9A108.0C26—C27—H27120.5
C10—C9—H9B108.0C28—C27—H27120.5
Sn1—C9—H9B108.0N2—C28—C27122.6 (3)
H9A—C9—H9B107.2N2—C28—H28118.7
C15—C10—C11116.4 (2)C27—C28—H28118.7
C15—C10—C9121.1 (2)
C1—Sn1—N1—C17−85.6 (2)C11—C12—C13—C141.1 (5)
C9—Sn1—N1—C1793.4 (2)C11—C12—C13—C16−177.6 (3)
N2—Sn1—N1—C17−176.1 (2)C12—C13—C14—C15−1.0 (4)
Cl1—Sn1—N1—C17−176.82 (15)C16—C13—C14—C15177.7 (3)
Cl2—Sn1—N1—C176.02 (19)C13—C14—C15—C100.3 (4)
C1—Sn1—N1—C2196.79 (17)C11—C10—C15—C140.4 (4)
C9—Sn1—N1—C21−84.15 (17)C9—C10—C15—C14179.6 (2)
N2—Sn1—N1—C216.36 (15)C21—N1—C17—C18−0.5 (4)
Cl1—Sn1—N1—C215.6 (3)Sn1—N1—C17—C18−177.98 (19)
Cl2—Sn1—N1—C21−171.54 (15)N1—C17—C18—C192.5 (4)
C1—Sn1—N2—C2890.9 (2)C17—C18—C19—C20−1.6 (5)
C9—Sn1—N2—C28−88.3 (2)C18—C19—C20—C21−1.1 (5)
N1—Sn1—N2—C28−177.6 (2)C18—C19—C20—C22178.9 (3)
Cl1—Sn1—N2—C282.21 (19)C17—N1—C21—C20−2.4 (3)
Cl2—Sn1—N2—C28−170.65 (16)Sn1—N1—C21—C20175.29 (18)
C1—Sn1—N2—C25−99.24 (16)C17—N1—C21—C25177.6 (2)
C9—Sn1—N2—C2581.58 (17)Sn1—N1—C21—C25−4.7 (3)
N1—Sn1—N2—C25−7.69 (15)C19—C20—C21—N13.2 (4)
Cl1—Sn1—N2—C25172.09 (15)C22—C20—C21—N1−176.7 (2)
Cl2—Sn1—N2—C25−0.8 (3)C19—C20—C21—C25−176.8 (2)
N2—Sn1—C1—C283.16 (19)C22—C20—C21—C253.3 (4)
N1—Sn1—C1—C213.03 (19)C21—C20—C22—C23−0.5 (5)
Cl1—Sn1—C1—C2176.07 (19)C19—C20—C22—C23179.6 (3)
Cl2—Sn1—C1—C2−79.34 (19)C20—C22—C23—C24−2.2 (6)
Sn1—C1—C2—C3−94.0 (3)C22—C23—C24—C26−179.6 (3)
Sn1—C1—C2—C783.4 (2)C22—C23—C24—C252.0 (5)
C7—C2—C3—C4−1.9 (4)C28—N2—C25—C24−0.2 (3)
C1—C2—C3—C4175.6 (2)Sn1—N2—C25—C24−170.55 (17)
C2—C3—C4—C5−1.0 (4)C28—N2—C25—C21178.7 (2)
C3—C4—C5—C62.8 (4)Sn1—N2—C25—C218.3 (3)
C3—C4—C5—C8−175.7 (3)C26—C24—C25—N21.2 (4)
C4—C5—C6—C7−1.6 (4)C23—C24—C25—N2179.7 (2)
C8—C5—C6—C7176.9 (3)C26—C24—C25—C21−177.7 (2)
C5—C6—C7—C2−1.3 (4)C23—C24—C25—C210.9 (3)
C3—C2—C7—C63.0 (4)N1—C21—C25—N2−2.4 (3)
C1—C2—C7—C6−174.5 (2)C20—C21—C25—N2177.6 (2)
N2—Sn1—C9—C1016.46 (19)N1—C21—C25—C24176.5 (2)
N1—Sn1—C9—C1086.56 (19)C20—C21—C25—C24−3.5 (3)
Cl1—Sn1—C9—C10−76.48 (19)C25—C24—C26—C27−1.0 (4)
Cl2—Sn1—C9—C10178.91 (19)C23—C24—C26—C27−179.5 (3)
Sn1—C9—C10—C15−90.4 (3)C24—C26—C27—C280.0 (5)
Sn1—C9—C10—C1188.7 (3)C25—N2—C28—C27−1.0 (4)
C15—C10—C11—C12−0.3 (4)Sn1—N2—C28—C27168.7 (2)
C9—C10—C11—C12−179.5 (3)C26—C27—C28—N21.1 (5)
C10—C11—C12—C13−0.4 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5335).

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