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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1676.
Published online 2009 November 25. doi:  10.1107/S1600536809049381
PMCID: PMC2971954

Dichloridobis(4-chloro­benz­yl)(4,4′-dimethyl-2,2′-bipyridine-κ2 N,N′)tin(IV)

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1676-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6Cl)2Cl2(C12H12N2)]
  • M r = 624.96
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1676-efi1.jpg
  • a = 11.4035 (6) Å
  • b = 14.6804 (8) Å
  • c = 16.9270 (9) Å
  • β = 101.9182 (9)°
  • V = 2772.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.32 mm−1
  • T = 293 K
  • 0.30 × 0.28 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.692, T max = 0.778
  • 15766 measured reflections
  • 6263 independent reflections
  • 4883 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.095
  • S = 1.00
  • 6263 reflections
  • 300 parameters
  • H-atom parameters constrained
  • Δρmax = 0.78 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049381/xu2682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049381/xu2682Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

[Sn(C7H6Cl)2Cl2(C12H12N2)]F(000) = 1248
Mr = 624.96Dx = 1.497 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer6263 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

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 = 1.00w = 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 Å3
0 restraintsΔρmin = −0.49 e Å3

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2682).

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