metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Bis{μ-2-[(N,N-diiso­propyl­carbamo­thio­yl)sulfan­yl]acetato-κ2O:O′}bis­­(bis­­(4-chloro­benz­yl){2-[(N,N-diiso­propyl­carbamo­thio­yl)sulfan­yl]acetato-κ2O,O′}tin(IV))

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 20 April 2011; accepted 26 April 2011; online 7 May 2011)

The dinuclear title complex, [Sn2(C7H6Cl)4(C9H16NO2S2)4], lies on a center of inversion. The SnIV atoms are chelated by one of the two carboxyl­ate ions; the other carboxyl­ate ion bridges two metal atoms. The geometry of the six-coordinate SnIV atom is a distorted trans-C2SnO4 octa­hedron [C—Sn—C = 155.32 (8)°].

Related literature

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961[Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.]). For the synthesis of the carb­oxy­lic acid, see: Nachmias (1952[Nachmias, G. (1952). Ann. Chim. 12, 584-631.]). For a review of the crystal structures of organotin carboxyl­ates, see: Tiekink (1991[Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.], 1994[Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn2(C7H6Cl)4(C9H16NO2S2)4]

  • Mr = 1677.04

  • Triclinic, [P \overline 1]

  • a = 11.0257 (1) Å

  • b = 13.1588 (2) Å

  • c = 14.5369 (2) Å

  • α = 96.4464 (5)°

  • β = 101.0660 (5)°

  • γ = 112.8168 (5)°

  • V = 1866.82 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.09 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.773, Tmax = 0.854

  • 17479 measured reflections

  • 8479 independent reflections

  • 7912 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.083

  • S = 0.93

  • 8479 reflections

  • 406 parameters

  • H-atom parameters constrained

  • Δρmax = 1.36 e Å−3

  • Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Diorganotin dicarboxylates are generally six-coordinate compounds as the carboxyl –CO2 portion of the anion functions either in a chelating or in a bridging mode (Tiekink, 1991, 1994). The title compound (Scheme I) exists as a centrosymmetric dinuclear molecule in which the anion of one formula unit functions in a chelating mode whereas the other anion functions in a chelating mode (Fig. 1). In dinuclear [Sn(C7H6Cl)2(C9H16NO2S2)2]2, the SnIV atom is chelated by one of the two carboxylate ions; the other carboxylate ion bridges two metal atoms. The geometry of the six-coordinate SnIV atom is a trans-C2SnO4 octahedron [C–Sn–C 155.32 (8) °]. The chelation is not isobidentate.

Related literature top

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961). For the synthesis of the carboxylic acid, see: Nachmias (1952). For a review of the crystal structures of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Di(4-chlorobenzyl)tin oxide was prepared by the base hydrolysis of di(4-chlorobenzyl)tin dichloride with 10% sodium hydroxide. The diorganotin dichloride was synthesized by the direct reaction of 4-chlorobenzyl chloride and metallic tin according to a literature procedure (Sisido et al., 1961). The carboxylic acid was synthesized by using literature procedure (Nachmias, 1952). The diorganotin oxide (0.78 g, 2 mmol) and N,N-diisopropyldithiocarbamylacetic acid (0.94 g, 2 mmol) were heated in ethanol (100 ml) for an hour until the oxide dissolved. The solution was filtered; slow evaporation of the filtrate gave colorless crystals.

Refinement top

H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Sn(C7H6Cl)2(C9H16NO2S2)2]2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Bis{µ-2-[(N,N-diisopropylcarbamothioyl)sulfanyl]acetato- κ2O:O'}bis(bis(4-chlorobenzyl){2-[(N,N- diisopropylcarbamothioyl)sulfanyl]acetato-κ2O,O'}tin(IV)) top
Crystal data top
[Sn2(C7H6Cl)4(C9H16NO2S4)2]Z = 1
Mr = 1677.04F(000) = 860
Triclinic, P1Dx = 1.492 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.0257 (1) ÅCell parameters from 9894 reflections
b = 13.1588 (2) Åθ = 2.5–28.4°
c = 14.5369 (2) ŵ = 1.09 mm1
α = 96.4464 (5)°T = 100 K
β = 101.0660 (5)°Block, colorless
γ = 112.8168 (5)°0.25 × 0.20 × 0.15 mm
V = 1866.82 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer
8479 independent reflections
Radiation source: fine-focus sealed tube7912 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.773, Tmax = 0.854k = 1716
17479 measured reflectionsl = 1818
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0633P)2 + 1.4914P]
where P = (Fo2 + 2Fc2)/3
8479 reflections(Δ/σ)max = 0.001
406 parametersΔρmax = 1.36 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
[Sn2(C7H6Cl)4(C9H16NO2S4)2]γ = 112.8168 (5)°
Mr = 1677.04V = 1866.82 (4) Å3
Triclinic, P1Z = 1
a = 11.0257 (1) ÅMo Kα radiation
b = 13.1588 (2) ŵ = 1.09 mm1
c = 14.5369 (2) ÅT = 100 K
α = 96.4464 (5)°0.25 × 0.20 × 0.15 mm
β = 101.0660 (5)°
Data collection top
Bruker SMART APEX
diffractometer
8479 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7912 reflections with I > 2σ(I)
Tmin = 0.773, Tmax = 0.854Rint = 0.014
17479 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 0.93Δρmax = 1.36 e Å3
8479 reflectionsΔρmin = 0.40 e Å3
406 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.406607 (11)0.336032 (10)0.363697 (8)0.01541 (5)
Cl10.79909 (7)0.41135 (6)0.03727 (5)0.04089 (15)
Cl20.49005 (7)0.19243 (6)0.83012 (4)0.04131 (15)
S10.20626 (5)0.00123 (4)0.06705 (3)0.02075 (10)
S20.28467 (6)0.04328 (4)0.26242 (4)0.02568 (11)
S30.89452 (5)0.59366 (4)0.67643 (3)0.01785 (10)
S40.96621 (5)0.63196 (4)0.49095 (3)0.01809 (10)
O10.47770 (14)0.23694 (12)0.27828 (10)0.0198 (3)
O20.27222 (14)0.21691 (12)0.20565 (10)0.0199 (3)
O30.59477 (13)0.37482 (11)0.46061 (10)0.0181 (3)
O40.64367 (13)0.55367 (11)0.52227 (10)0.0169 (3)
N10.05428 (17)0.17675 (14)0.12945 (12)0.0187 (3)
N21.08837 (17)0.78195 (14)0.65749 (12)0.0200 (3)
C10.4573 (2)0.47745 (16)0.29490 (14)0.0191 (4)
H1A0.37300.47860.25740.023*
H1B0.50660.54830.34380.023*
C20.54474 (19)0.46880 (16)0.22990 (14)0.0184 (4)
C30.4923 (2)0.43674 (17)0.13091 (15)0.0215 (4)
H30.40180.42640.10370.026*
C40.5703 (2)0.41951 (18)0.07087 (15)0.0255 (4)
H40.53370.39750.00340.031*
C50.7014 (2)0.43497 (18)0.11127 (17)0.0264 (4)
C60.7578 (2)0.46882 (18)0.20934 (16)0.0251 (4)
H60.84890.48000.23600.030*
C70.6792 (2)0.48612 (17)0.26803 (15)0.0214 (4)
H70.71750.51010.33530.026*
C80.27651 (19)0.20341 (16)0.41890 (14)0.0192 (4)
H8A0.18840.20900.41260.023*
H8B0.25840.13040.37910.023*
C90.33225 (19)0.20376 (15)0.52141 (14)0.0177 (4)
C100.4326 (2)0.16432 (18)0.54665 (16)0.0232 (4)
H100.46740.13920.49820.028*
C110.4821 (2)0.16130 (19)0.64091 (17)0.0272 (4)
H110.55060.13480.65720.033*
C120.4302 (2)0.19759 (18)0.71133 (16)0.0258 (4)
C130.3319 (2)0.23779 (17)0.68898 (15)0.0232 (4)
H130.29760.26290.73770.028*
C140.2840 (2)0.24098 (16)0.59425 (15)0.0207 (4)
H140.21690.26910.57870.025*
C150.37035 (19)0.19069 (16)0.20849 (14)0.0185 (4)
C160.3714 (2)0.10820 (17)0.12758 (15)0.0215 (4)
H16A0.43170.07300.15360.026*
H16B0.41070.15030.08030.026*
C170.1718 (2)0.08442 (16)0.15656 (14)0.0188 (4)
C180.0199 (2)0.26663 (17)0.18707 (15)0.0218 (4)
H180.06960.32760.14910.026*
C190.1204 (2)0.32062 (19)0.19771 (17)0.0281 (4)
H19A0.13130.34390.13450.042*
H19B0.08580.38660.22640.042*
H19C0.20860.26600.23900.042*
C200.0031 (3)0.2275 (2)0.28203 (17)0.0324 (5)
H20A0.06820.19360.27080.049*
H20B0.08350.17150.32440.049*
H20C0.03940.29210.31210.049*
C210.0494 (2)0.19933 (17)0.03826 (14)0.0213 (4)
H210.02170.12860.01260.026*
C220.0516 (2)0.2910 (2)0.03654 (15)0.0281 (4)
H22A0.04010.27070.04560.042*
H22B0.11440.29880.09730.042*
H22C0.08200.36260.01490.042*
C230.1897 (2)0.22522 (19)0.05571 (16)0.0263 (4)
H23A0.18340.16400.10410.039*
H23B0.22190.29600.07840.039*
H23C0.25370.23230.00420.039*
C240.66742 (17)0.46904 (15)0.52041 (12)0.0144 (3)
C250.78688 (18)0.46587 (15)0.58999 (14)0.0176 (3)
H25A0.84350.44590.55260.021*
H25B0.75100.40490.62490.021*
C260.99540 (18)0.68054 (16)0.60723 (14)0.0167 (3)
C271.1767 (2)0.87019 (16)0.61264 (15)0.0209 (4)
H271.23610.93550.66670.025*
C281.0951 (2)0.91474 (17)0.54522 (16)0.0237 (4)
H28A1.03530.93560.57750.036*
H28B1.04000.85620.48760.036*
H28C1.15750.98110.52710.036*
C291.2744 (2)0.83578 (19)0.56923 (18)0.0282 (5)
H29A1.32350.80790.61620.042*
H29B1.33970.90120.55190.042*
H29C1.22260.77620.51180.042*
C301.1115 (2)0.81703 (18)0.76301 (15)0.0267 (4)
H301.04870.75180.78480.032*
C311.0746 (2)0.9154 (2)0.78689 (17)0.0342 (5)
H31A0.98120.89600.75090.051*
H31B1.13730.98210.76940.051*
H31C1.08180.93120.85570.051*
C321.2568 (3)0.8413 (2)0.81602 (17)0.0349 (5)
H32A1.26980.86460.88490.052*
H32B1.32150.90180.79330.052*
H32C1.27230.77320.80380.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01341 (8)0.01605 (8)0.01545 (8)0.00530 (5)0.00327 (5)0.00229 (5)
Cl10.0447 (3)0.0428 (3)0.0452 (4)0.0206 (3)0.0307 (3)0.0069 (3)
Cl20.0425 (3)0.0562 (4)0.0249 (3)0.0218 (3)0.0028 (2)0.0132 (3)
S10.0221 (2)0.0181 (2)0.0158 (2)0.00386 (18)0.00156 (18)0.00244 (17)
S20.0279 (3)0.0224 (2)0.0224 (2)0.0108 (2)0.0030 (2)0.00348 (19)
S30.0161 (2)0.0179 (2)0.0152 (2)0.00339 (17)0.00239 (16)0.00325 (17)
S40.0186 (2)0.0196 (2)0.0171 (2)0.00896 (18)0.00526 (17)0.00303 (17)
O10.0156 (6)0.0191 (6)0.0208 (7)0.0053 (5)0.0023 (5)0.0001 (5)
O20.0169 (6)0.0217 (7)0.0207 (7)0.0088 (5)0.0036 (5)0.0029 (5)
O30.0155 (6)0.0164 (6)0.0192 (6)0.0057 (5)0.0015 (5)0.0002 (5)
O40.0149 (6)0.0175 (6)0.0202 (7)0.0082 (5)0.0055 (5)0.0039 (5)
N10.0189 (8)0.0218 (8)0.0157 (8)0.0091 (6)0.0025 (6)0.0056 (6)
N20.0182 (8)0.0181 (8)0.0202 (8)0.0044 (6)0.0048 (6)0.0029 (6)
C10.0186 (9)0.0193 (9)0.0204 (9)0.0079 (7)0.0071 (7)0.0046 (7)
C20.0183 (9)0.0172 (8)0.0191 (9)0.0059 (7)0.0064 (7)0.0036 (7)
C30.0220 (9)0.0228 (9)0.0197 (9)0.0091 (8)0.0054 (8)0.0049 (7)
C40.0332 (11)0.0258 (10)0.0185 (9)0.0119 (9)0.0103 (8)0.0038 (8)
C50.0305 (11)0.0235 (10)0.0299 (11)0.0108 (8)0.0179 (9)0.0071 (8)
C60.0194 (9)0.0248 (10)0.0319 (11)0.0081 (8)0.0098 (8)0.0078 (8)
C70.0186 (9)0.0222 (9)0.0213 (9)0.0058 (7)0.0058 (7)0.0055 (8)
C80.0152 (8)0.0182 (9)0.0219 (9)0.0055 (7)0.0039 (7)0.0021 (7)
C90.0140 (8)0.0150 (8)0.0234 (9)0.0048 (7)0.0059 (7)0.0045 (7)
C100.0207 (9)0.0244 (10)0.0278 (10)0.0117 (8)0.0086 (8)0.0055 (8)
C110.0212 (10)0.0318 (11)0.0322 (11)0.0145 (9)0.0053 (8)0.0105 (9)
C120.0236 (10)0.0268 (10)0.0234 (10)0.0069 (8)0.0034 (8)0.0089 (8)
C130.0229 (9)0.0225 (9)0.0230 (10)0.0073 (8)0.0082 (8)0.0043 (8)
C140.0196 (9)0.0184 (9)0.0258 (10)0.0081 (7)0.0086 (8)0.0057 (8)
C150.0172 (8)0.0184 (8)0.0185 (9)0.0061 (7)0.0049 (7)0.0032 (7)
C160.0183 (9)0.0209 (9)0.0205 (9)0.0057 (7)0.0033 (7)0.0014 (7)
C170.0204 (9)0.0198 (9)0.0180 (9)0.0109 (7)0.0037 (7)0.0033 (7)
C180.0214 (9)0.0240 (9)0.0200 (9)0.0078 (8)0.0060 (7)0.0098 (8)
C190.0294 (11)0.0255 (10)0.0333 (12)0.0135 (9)0.0086 (9)0.0130 (9)
C200.0350 (12)0.0403 (13)0.0239 (11)0.0147 (10)0.0132 (9)0.0086 (10)
C210.0197 (9)0.0239 (9)0.0165 (9)0.0075 (8)0.0003 (7)0.0049 (7)
C220.0313 (11)0.0325 (11)0.0186 (10)0.0131 (9)0.0043 (8)0.0018 (8)
C230.0192 (9)0.0289 (10)0.0283 (11)0.0096 (8)0.0022 (8)0.0048 (9)
C240.0112 (7)0.0167 (8)0.0145 (8)0.0039 (6)0.0052 (6)0.0032 (7)
C250.0144 (8)0.0145 (8)0.0198 (9)0.0037 (7)0.0010 (7)0.0021 (7)
C260.0141 (8)0.0184 (8)0.0194 (9)0.0084 (7)0.0044 (7)0.0051 (7)
C270.0182 (9)0.0179 (9)0.0263 (10)0.0056 (7)0.0083 (8)0.0059 (8)
C280.0235 (10)0.0179 (9)0.0310 (11)0.0076 (8)0.0101 (8)0.0086 (8)
C290.0215 (10)0.0270 (10)0.0415 (13)0.0123 (8)0.0145 (9)0.0093 (9)
C300.0259 (10)0.0228 (10)0.0185 (10)0.0003 (8)0.0026 (8)0.0011 (8)
C310.0273 (11)0.0430 (13)0.0238 (11)0.0110 (10)0.0035 (9)0.0072 (10)
C320.0375 (13)0.0333 (12)0.0269 (11)0.0144 (10)0.0040 (10)0.0021 (9)
Geometric parameters (Å, º) top
Sn1—O32.1083 (13)C12—C131.381 (3)
Sn1—C82.136 (2)C13—C141.389 (3)
Sn1—C12.1451 (19)C13—H130.9500
Sn1—O12.1585 (14)C14—H140.9500
Sn1—O4i2.3661 (13)C15—C161.514 (3)
Sn1—O22.4524 (14)C16—H16A0.9900
Cl1—C51.744 (2)C16—H16B0.9900
Cl2—C121.745 (2)C18—C201.520 (3)
S1—C171.795 (2)C18—C191.525 (3)
S1—C161.798 (2)C18—H181.0000
S2—C171.663 (2)C19—H19A0.9800
S3—C251.7945 (19)C19—H19B0.9800
S3—C261.805 (2)C19—H19C0.9800
S4—C261.6609 (19)C20—H20A0.9800
O1—C151.282 (2)C20—H20B0.9800
O2—C151.252 (2)C20—H20C0.9800
O3—C241.286 (2)C21—C221.520 (3)
O4—C241.238 (2)C21—C231.528 (3)
O4—Sn1i2.3661 (13)C21—H211.0000
N1—C171.336 (3)C22—H22A0.9800
N1—C211.489 (2)C22—H22B0.9800
N1—C181.497 (2)C22—H22C0.9800
N2—C261.341 (2)C23—H23A0.9800
N2—C301.494 (3)C23—H23B0.9800
N2—C271.503 (2)C23—H23C0.9800
C1—C21.499 (3)C24—C251.517 (2)
C1—H1A0.9900C25—H25A0.9900
C1—H1B0.9900C25—H25B0.9900
C2—C31.392 (3)C27—C281.521 (3)
C2—C71.397 (3)C27—C291.529 (3)
C3—C41.396 (3)C27—H271.0000
C3—H30.9500C28—H28A0.9800
C4—C51.377 (3)C28—H28B0.9800
C4—H40.9500C28—H28C0.9800
C5—C61.386 (3)C29—H29A0.9800
C6—C71.387 (3)C29—H29B0.9800
C6—H60.9500C29—H29C0.9800
C7—H70.9500C30—C311.523 (3)
C8—C91.498 (3)C30—C321.529 (3)
C8—H8A0.9900C30—H301.0000
C8—H8B0.9900C31—H31A0.9800
C9—C141.395 (3)C31—H31B0.9800
C9—C101.400 (3)C31—H31C0.9800
C10—C111.385 (3)C32—H32A0.9800
C10—H100.9500C32—H32B0.9800
C11—C121.389 (3)C32—H32C0.9800
C11—H110.9500
O3—Sn1—C899.59 (6)S2—C17—S1119.19 (12)
O3—Sn1—C1101.45 (6)N1—C18—C20112.71 (18)
C8—Sn1—C1155.32 (8)N1—C18—C19112.50 (16)
O3—Sn1—O181.59 (5)C20—C18—C19113.09 (18)
C8—Sn1—O197.84 (7)N1—C18—H18105.9
C1—Sn1—O197.86 (6)C20—C18—H18105.9
O3—Sn1—O4i89.62 (5)C19—C18—H18105.9
C8—Sn1—O4i81.34 (6)C18—C19—H19A109.5
C1—Sn1—O4i86.03 (6)C18—C19—H19B109.5
O1—Sn1—O4i170.93 (5)H19A—C19—H19B109.5
O3—Sn1—O2138.32 (5)C18—C19—H19C109.5
C8—Sn1—O285.30 (6)H19A—C19—H19C109.5
C1—Sn1—O287.52 (6)H19B—C19—H19C109.5
O1—Sn1—O256.78 (5)C18—C20—H20A109.5
O4i—Sn1—O2131.86 (5)C18—C20—H20B109.5
C17—S1—C16101.28 (10)H20A—C20—H20B109.5
C25—S3—C26102.78 (9)C18—C20—H20C109.5
C15—O1—Sn197.25 (12)H20A—C20—H20C109.5
C15—O2—Sn184.57 (11)H20B—C20—H20C109.5
C24—O3—Sn1124.97 (12)N1—C21—C22111.51 (17)
C24—O4—Sn1i134.92 (12)N1—C21—C23111.22 (17)
C17—N1—C21122.40 (16)C22—C21—C23112.33 (18)
C17—N1—C18122.23 (16)N1—C21—H21107.2
C21—N1—C18115.34 (16)C22—C21—H21107.2
C26—N2—C30122.54 (17)C23—C21—H21107.2
C26—N2—C27123.08 (17)C21—C22—H22A109.5
C30—N2—C27114.38 (16)C21—C22—H22B109.5
C2—C1—Sn1109.47 (13)H22A—C22—H22B109.5
C2—C1—H1A109.8C21—C22—H22C109.5
Sn1—C1—H1A109.8H22A—C22—H22C109.5
C2—C1—H1B109.8H22B—C22—H22C109.5
Sn1—C1—H1B109.8C21—C23—H23A109.5
H1A—C1—H1B108.2C21—C23—H23B109.5
C3—C2—C7118.34 (18)H23A—C23—H23B109.5
C3—C2—C1121.19 (18)C21—C23—H23C109.5
C7—C2—C1120.35 (18)H23A—C23—H23C109.5
C2—C3—C4121.21 (19)H23B—C23—H23C109.5
C2—C3—H3119.4O4—C24—O3124.49 (17)
C4—C3—H3119.4O4—C24—C25122.89 (16)
C5—C4—C3118.7 (2)O3—C24—C25112.62 (15)
C5—C4—H4120.6C24—C25—S3115.96 (13)
C3—C4—H4120.6C24—C25—H25A108.3
C4—C5—C6121.64 (19)S3—C25—H25A108.3
C4—C5—Cl1119.24 (18)C24—C25—H25B108.3
C6—C5—Cl1119.12 (17)S3—C25—H25B108.3
C5—C6—C7118.9 (2)H25A—C25—H25B107.4
C5—C6—H6120.5N2—C26—S4126.15 (15)
C7—C6—H6120.5N2—C26—S3114.39 (14)
C6—C7—C2121.11 (19)S4—C26—S3119.44 (11)
C6—C7—H7119.4N2—C27—C28112.35 (16)
C2—C7—H7119.4N2—C27—C29113.67 (16)
C9—C8—Sn1114.60 (13)C28—C27—C29113.65 (18)
C9—C8—H8A108.6N2—C27—H27105.4
Sn1—C8—H8A108.6C28—C27—H27105.4
C9—C8—H8B108.6C29—C27—H27105.4
Sn1—C8—H8B108.6C27—C28—H28A109.5
H8A—C8—H8B107.6C27—C28—H28B109.5
C14—C9—C10118.02 (19)H28A—C28—H28B109.5
C14—C9—C8121.19 (17)C27—C28—H28C109.5
C10—C9—C8120.77 (18)H28A—C28—H28C109.5
C11—C10—C9121.24 (19)H28B—C28—H28C109.5
C11—C10—H10119.4C27—C29—H29A109.5
C9—C10—H10119.4C27—C29—H29B109.5
C10—C11—C12119.10 (19)H29A—C29—H29B109.5
C10—C11—H11120.5C27—C29—H29C109.5
C12—C11—H11120.5H29A—C29—H29C109.5
C13—C12—C11121.1 (2)H29B—C29—H29C109.5
C13—C12—Cl2119.33 (17)N2—C30—C31111.48 (18)
C11—C12—Cl2119.54 (17)N2—C30—C32110.90 (19)
C12—C13—C14119.1 (2)C31—C30—C32112.58 (19)
C12—C13—H13120.5N2—C30—H30107.2
C14—C13—H13120.5C31—C30—H30107.2
C13—C14—C9121.42 (19)C32—C30—H30107.2
C13—C14—H14119.3C30—C31—H31A109.5
C9—C14—H14119.3C30—C31—H31B109.5
O2—C15—O1121.24 (18)H31A—C31—H31B109.5
O2—C15—C16121.85 (17)C30—C31—H31C109.5
O1—C15—C16116.83 (17)H31A—C31—H31C109.5
C15—C16—S1114.07 (14)H31B—C31—H31C109.5
C15—C16—H16A108.7C30—C32—H32A109.5
S1—C16—H16A108.7C30—C32—H32B109.5
C15—C16—H16B108.7H32A—C32—H32B109.5
S1—C16—H16B108.7C30—C32—H32C109.5
H16A—C16—H16B107.6H32A—C32—H32C109.5
N1—C17—S2126.05 (15)H32B—C32—H32C109.5
N1—C17—S1114.75 (14)
O3—Sn1—O1—C15175.44 (12)C12—C13—C14—C90.5 (3)
C8—Sn1—O1—C1576.84 (12)C10—C9—C14—C130.9 (3)
C1—Sn1—O1—C1584.06 (12)C8—C9—C14—C13177.72 (18)
O2—Sn1—O1—C152.27 (11)Sn1—O2—C15—O13.81 (18)
O3—Sn1—O2—C151.10 (14)Sn1—O2—C15—C16179.68 (18)
C8—Sn1—O2—C15100.24 (12)Sn1—O1—C15—O24.3 (2)
C1—Sn1—O2—C15103.39 (12)Sn1—O1—C15—C16178.97 (14)
O1—Sn1—O2—C152.31 (11)O2—C15—C16—S133.0 (2)
O4i—Sn1—O2—C15174.20 (10)O1—C15—C16—S1150.36 (15)
C8—Sn1—O3—C24115.23 (15)C17—S1—C16—C1570.97 (16)
C1—Sn1—O3—C2451.79 (15)C21—N1—C17—S2171.63 (15)
O1—Sn1—O3—C24148.18 (15)C18—N1—C17—S210.5 (3)
O4i—Sn1—O3—C2434.08 (14)C21—N1—C17—S19.1 (2)
O2—Sn1—O3—C24151.06 (13)C18—N1—C17—S1168.77 (14)
O3—Sn1—C1—C271.86 (14)C16—S1—C17—N1177.62 (15)
C8—Sn1—C1—C2140.16 (17)C16—S1—C17—S21.75 (14)
O1—Sn1—C1—C211.10 (14)C17—N1—C18—C2068.3 (2)
O4i—Sn1—C1—C2160.66 (13)C21—N1—C18—C20113.7 (2)
O2—Sn1—C1—C267.08 (13)C17—N1—C18—C1961.0 (2)
Sn1—C1—C2—C3104.94 (18)C21—N1—C18—C19116.98 (19)
Sn1—C1—C2—C771.1 (2)C17—N1—C21—C22105.8 (2)
C7—C2—C3—C41.5 (3)C18—N1—C21—C2272.1 (2)
C1—C2—C3—C4174.57 (19)C17—N1—C21—C23127.9 (2)
C2—C3—C4—C50.1 (3)C18—N1—C21—C2354.1 (2)
C3—C4—C5—C61.1 (3)Sn1i—O4—C24—O3118.97 (18)
C3—C4—C5—Cl1178.89 (16)Sn1i—O4—C24—C2560.7 (2)
C4—C5—C6—C70.8 (3)Sn1—O3—C24—O47.9 (3)
Cl1—C5—C6—C7179.18 (16)Sn1—O3—C24—C25171.81 (11)
C5—C6—C7—C20.7 (3)O4—C24—C25—S30.3 (2)
C3—C2—C7—C61.8 (3)O3—C24—C25—S3179.99 (13)
C1—C2—C7—C6174.30 (18)C26—S3—C25—C2477.30 (15)
O3—Sn1—C8—C922.00 (14)C30—N2—C26—S4177.53 (15)
C1—Sn1—C8—C9126.20 (18)C27—N2—C26—S43.2 (3)
O1—Sn1—C8—C9104.73 (14)C30—N2—C26—S33.3 (2)
O4i—Sn1—C8—C966.14 (13)C27—N2—C26—S3175.90 (14)
O2—Sn1—C8—C9160.25 (14)C25—S3—C26—N2178.38 (14)
Sn1—C8—C9—C14104.11 (18)C25—S3—C26—S42.42 (13)
Sn1—C8—C9—C1077.3 (2)C26—N2—C27—C2866.6 (2)
C14—C9—C10—C110.5 (3)C30—N2—C27—C28112.7 (2)
C8—C9—C10—C11178.15 (19)C26—N2—C27—C2964.3 (2)
C9—C10—C11—C120.4 (3)C30—N2—C27—C29116.4 (2)
C10—C11—C12—C130.9 (3)C26—N2—C30—C31115.4 (2)
C10—C11—C12—Cl2179.14 (17)C27—N2—C30—C3163.9 (2)
C11—C12—C13—C140.5 (3)C26—N2—C30—C32118.3 (2)
Cl2—C12—C13—C14179.55 (16)C27—N2—C30—C3262.4 (2)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Sn2(C7H6Cl)4(C9H16NO2S4)2]
Mr1677.04
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)11.0257 (1), 13.1588 (2), 14.5369 (2)
α, β, γ (°)96.4464 (5), 101.0660 (5), 112.8168 (5)
V3)1866.82 (4)
Z1
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.773, 0.854
No. of measured, independent and
observed [I > 2σ(I)] reflections
17479, 8479, 7912
Rint0.014
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.083, 0.93
No. of reflections8479
No. of parameters406
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.36, 0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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

References

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First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNachmias, G. (1952). Ann. Chim. 12, 584–631.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541.  CrossRef Web of Science Google Scholar
First citationTiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23.  CrossRef CAS Web of Science Google Scholar
First citationTiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116.  Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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