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

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ISSN: 2056-9890

(2-Methyl­quinolin-8-olato-κ2N,O)di­phenyl­(thio­cyanato-κN)tin(IV)

aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 December 2009; accepted 30 December 2009; online 16 January 2010)

The SnIV atom in the title compound, [Sn(C6H5)2(C10H8NO)(NCS)], is chelated by the 2-methyl­quinolin-8-olate anion and is five-coordinate in a trigonal-bipramidal geometry [C—Sn—C = 133.47 (13) and 138.77 (12)°]. There are two independent mol­ecules of similar conformation in the asymmetric unit.

Related literature

The title compound is an unusual example of a diorganotin compound having different anionic groups; for mixed chelated diorganotin compounds, see: Ng (1999[Ng, S. W. (1999). J. Organomet. Chem. 585, 12-17.]). The diorganotin derivatives of 8-hydroxy­quinolines are bis-­chelate compounds; for the crystal structure of diphenyl­bis(8-hydroxy­quinolinato)tin, see: Linden et al. (2005[Linden, A., Basu Baul, T. S. & Mizar, A. (2005). Acta Cryst. E61, m27-m29.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)2(C10H8NO)(NCS)]

  • Mr = 489.14

  • Triclinic, [P \overline 1]

  • a = 9.0093 (5) Å

  • b = 11.5809 (6) Å

  • c = 20.5129 (11) Å

  • α = 83.7166 (7)°

  • β = 85.4123 (7)°

  • γ = 78.2441 (7)°

  • V = 2079.09 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.35 mm−1

  • T = 295 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.615, Tmax = 0.775

  • 19942 measured reflections

  • 9461 independent reflections

  • 7796 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.103

  • S = 1.04

  • 9461 reflections

  • 507 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.96 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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). publCIF. In preparation.]).

Supporting information


Related literature top

The diorganotin compound is an unusual example of a diorganotin compounds having different anionic groups; for mixed chelated diorganotin compounds, see: Ng (1999). The diorganotin derivatives of 8-hydroxyquinolines are bischelates compounds; for the crystal structure of diphenylbis(8-hydroxyquinolinato)tin, see: Linden et al. (2005).

Experimental top

Diphenyltin dichloride (0.34 g,1 mmol), potassium thiocyanate (0.10 g, 1 mol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were dissolved in methanol (10 ml). The white participate was collected and crystallized from dichloromethane; m.p. 466–467 K.

Refinement top

H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Structure description top

The diorganotin compound is an unusual example of a diorganotin compounds having different anionic groups; for mixed chelated diorganotin compounds, see: Ng (1999). The diorganotin derivatives of 8-hydroxyquinolines are bischelates compounds; for the crystal structure of diphenylbis(8-hydroxyquinolinato)tin, see: Linden et al. (2005).

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, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Sn(NCS)(C6H5)2(C10H8NO); ellipsoids are drawn at the 50% probability level and H atoms of arbitrary radius.
(2-Methylquinolin-8-olato-κ2N,O)diphenyl(thiocyanato- κN)tin(IV) top
Crystal data top
[Sn(C6H5)2(C10H8NO)(NCS)]Z = 4
Mr = 489.14F(000) = 976
Triclinic, P1Dx = 1.563 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0093 (5) ÅCell parameters from 9333 reflections
b = 11.5809 (6) Åθ = 2.3–28.3°
c = 20.5129 (11) ŵ = 1.35 mm1
α = 83.7166 (7)°T = 295 K
β = 85.4123 (7)°Prism, yellow
γ = 78.2441 (7)°0.40 × 0.20 × 0.20 mm
V = 2079.09 (19) Å3
Data collection top
Bruker SMART APEX
diffractometer
9461 independent reflections
Radiation source: fine-focus sealed tube7796 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.615, Tmax = 0.775k = 1513
19942 measured reflectionsl = 2626
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0543P)2 + 1.4929P]
where P = (Fo2 + 2Fc2)/3
9461 reflections(Δ/σ)max = 0.001
507 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.96 e Å3
Crystal data top
[Sn(C6H5)2(C10H8NO)(NCS)]γ = 78.2441 (7)°
Mr = 489.14V = 2079.09 (19) Å3
Triclinic, P1Z = 4
a = 9.0093 (5) ÅMo Kα radiation
b = 11.5809 (6) ŵ = 1.35 mm1
c = 20.5129 (11) ÅT = 295 K
α = 83.7166 (7)°0.40 × 0.20 × 0.20 mm
β = 85.4123 (7)°
Data collection top
Bruker SMART APEX
diffractometer
9461 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7796 reflections with I > 2σ(I)
Tmin = 0.615, Tmax = 0.775Rint = 0.021
19942 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.04Δρmax = 0.56 e Å3
9461 reflectionsΔρmin = 0.96 e Å3
507 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.82767 (2)0.23539 (2)0.420294 (10)0.03926 (8)
Sn20.09509 (2)0.75000 (2)0.091111 (10)0.03957 (8)
S10.88115 (18)0.08766 (12)0.64310 (6)0.0794 (4)
S20.2261 (2)0.87393 (15)0.13678 (6)0.0979 (5)
O10.6736 (3)0.3825 (2)0.43924 (11)0.0461 (6)
O20.2507 (3)0.5987 (2)0.08617 (11)0.0485 (6)
N10.8195 (3)0.3559 (2)0.32032 (13)0.0364 (6)
N20.7735 (4)0.1754 (3)0.52636 (17)0.0583 (8)
N30.0928 (3)0.6567 (3)0.19826 (13)0.0409 (6)
N40.1623 (4)0.7748 (3)0.01556 (17)0.0632 (9)
C11.0470 (3)0.2573 (3)0.44053 (15)0.0362 (6)
C21.0524 (4)0.3402 (4)0.48398 (19)0.0530 (9)
H2A0.96280.38110.50320.064*
C31.1910 (5)0.3624 (4)0.4989 (2)0.0619 (11)
H3A1.19350.41790.52810.074*
C41.3240 (4)0.3031 (4)0.4710 (2)0.0569 (10)
H4A1.41660.31890.48060.068*
C51.3190 (4)0.2207 (4)0.4290 (2)0.0571 (10)
H5A1.40920.17970.41040.068*
C61.1814 (4)0.1968 (3)0.41342 (18)0.0473 (8)
H6A1.18020.14010.38480.057*
C70.7258 (3)0.1086 (3)0.38270 (16)0.0380 (7)
C80.6944 (5)0.0112 (4)0.4234 (2)0.0568 (10)
H8A0.72880.00370.46560.068*
C90.6119 (6)0.0636 (4)0.4011 (2)0.0704 (13)
H9A0.58980.12770.42890.085*
C100.5626 (5)0.0448 (3)0.3391 (2)0.0595 (10)
H10A0.50770.09590.32460.071*
C110.5942 (5)0.0498 (4)0.29804 (19)0.0538 (9)
H11A0.56040.06300.25570.065*
C120.6760 (4)0.1255 (3)0.31938 (17)0.0448 (8)
H12A0.69810.18880.29090.054*
C130.6292 (4)0.4647 (3)0.38955 (16)0.0398 (7)
C140.5120 (4)0.5589 (3)0.39706 (19)0.0494 (8)
H14A0.45970.56740.43780.059*
C150.4700 (5)0.6433 (3)0.3433 (2)0.0578 (10)
H15A0.38920.70640.34910.069*
C160.5443 (5)0.6346 (3)0.2836 (2)0.0567 (10)
H16A0.51590.69200.24910.068*
C170.6650 (4)0.5383 (3)0.27379 (18)0.0450 (8)
C180.7069 (4)0.4531 (3)0.32630 (15)0.0368 (7)
C190.7480 (5)0.5186 (4)0.21314 (19)0.0561 (10)
H19A0.72530.57250.17660.067*
C200.8603 (5)0.4220 (4)0.20783 (18)0.0527 (9)
H20A0.91430.41020.16770.063*
C210.8959 (4)0.3393 (3)0.26282 (16)0.0416 (7)
C221.0172 (4)0.2313 (4)0.25659 (19)0.0533 (9)
H22A1.02110.20720.21310.080*
H22B0.99490.16850.28810.080*
H22C1.11340.24870.26460.080*
C230.8225 (4)0.1396 (4)0.5705 (2)0.0530 (9)
C240.1255 (4)0.7263 (3)0.07396 (15)0.0412 (7)
C250.1355 (4)0.6240 (4)0.04732 (19)0.0544 (9)
H25A0.04790.56820.03910.065*
C260.2744 (6)0.6036 (5)0.0328 (2)0.0715 (13)
H26A0.28000.53520.01400.086*
C270.4036 (5)0.6845 (5)0.0460 (2)0.0766 (14)
H27A0.49730.67040.03660.092*
C280.3966 (5)0.7849 (5)0.0727 (2)0.0754 (14)
H28A0.48560.83880.08170.091*
C290.2576 (5)0.8085 (4)0.0869 (2)0.0564 (9)
H29A0.25320.87810.10480.068*
C300.1809 (4)0.8951 (3)0.11689 (16)0.0409 (7)
C310.1905 (5)0.9914 (4)0.0717 (2)0.0618 (11)
H31A0.15460.99400.03020.074*
C320.2519 (6)1.0829 (4)0.0871 (2)0.0714 (13)
H32A0.25551.14770.05640.086*
C330.3074 (6)1.0797 (4)0.1464 (2)0.0700 (13)
H33A0.35331.14030.15600.084*
C340.2960 (6)0.9872 (4)0.1924 (2)0.0678 (12)
H34A0.32980.98720.23410.081*
C350.2356 (5)0.8945 (4)0.17824 (19)0.0544 (9)
H35A0.23120.83090.20970.065*
C360.2866 (4)0.5294 (3)0.14148 (17)0.0429 (7)
C370.4023 (5)0.4310 (4)0.1427 (2)0.0577 (10)
H37A0.45900.41120.10420.069*
C380.4349 (5)0.3606 (4)0.2019 (2)0.0636 (11)
H38A0.51390.29490.20190.076*
C390.3555 (5)0.3851 (4)0.2585 (2)0.0641 (12)
H39A0.37970.33650.29690.077*
C400.2356 (4)0.4844 (3)0.26010 (18)0.0501 (9)
C410.2027 (4)0.5574 (3)0.20114 (16)0.0395 (7)
C420.1439 (5)0.5205 (4)0.3162 (2)0.0636 (11)
H42A0.15990.47590.35640.076*
C430.0345 (5)0.6176 (4)0.31239 (18)0.0625 (11)
H43A0.02520.63890.34990.075*
C440.0077 (4)0.6889 (4)0.25189 (17)0.0490 (9)
C450.1110 (5)0.7978 (4)0.2472 (2)0.0627 (11)
H45A0.07240.85920.22000.094*
H45B0.13980.82280.29030.094*
H45C0.19810.78200.22820.094*
C460.1877 (5)0.8159 (4)0.0627 (2)0.0561 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03234 (12)0.05092 (15)0.03605 (12)0.01352 (10)0.00570 (8)0.00188 (9)
Sn20.03680 (13)0.04672 (14)0.03558 (12)0.01099 (10)0.00574 (9)0.00222 (9)
S10.1024 (10)0.0763 (8)0.0585 (7)0.0095 (7)0.0306 (7)0.0021 (6)
S20.1332 (14)0.1052 (11)0.0526 (7)0.0328 (10)0.0259 (8)0.0010 (7)
O10.0427 (13)0.0588 (15)0.0356 (12)0.0089 (11)0.0021 (10)0.0039 (10)
O20.0483 (14)0.0534 (15)0.0393 (12)0.0008 (11)0.0031 (10)0.0020 (11)
N10.0357 (13)0.0382 (14)0.0378 (14)0.0144 (11)0.0001 (11)0.0024 (11)
N20.0534 (19)0.074 (2)0.0500 (19)0.0213 (17)0.0110 (15)0.0059 (17)
N30.0406 (15)0.0485 (16)0.0362 (14)0.0165 (13)0.0022 (11)0.0003 (12)
N40.060 (2)0.078 (3)0.051 (2)0.0200 (18)0.0103 (16)0.0147 (18)
C10.0325 (15)0.0390 (17)0.0372 (16)0.0086 (13)0.0078 (12)0.0034 (13)
C20.0427 (19)0.060 (2)0.057 (2)0.0042 (17)0.0088 (16)0.0172 (18)
C30.064 (3)0.060 (3)0.069 (3)0.017 (2)0.026 (2)0.012 (2)
C40.0391 (19)0.069 (3)0.066 (2)0.0228 (18)0.0220 (17)0.014 (2)
C50.0316 (17)0.077 (3)0.055 (2)0.0008 (18)0.0008 (15)0.005 (2)
C60.0420 (18)0.052 (2)0.0474 (19)0.0037 (16)0.0059 (15)0.0088 (16)
C70.0309 (15)0.0376 (17)0.0440 (17)0.0060 (12)0.0029 (12)0.0023 (13)
C80.063 (2)0.055 (2)0.052 (2)0.0188 (19)0.0171 (18)0.0165 (17)
C90.090 (3)0.051 (2)0.076 (3)0.035 (2)0.017 (3)0.017 (2)
C100.071 (3)0.040 (2)0.073 (3)0.0240 (19)0.009 (2)0.0026 (18)
C110.058 (2)0.059 (2)0.051 (2)0.0237 (19)0.0120 (17)0.0034 (17)
C120.0468 (19)0.0461 (19)0.0440 (18)0.0190 (15)0.0043 (15)0.0044 (15)
C130.0374 (16)0.0450 (18)0.0410 (17)0.0152 (14)0.0038 (13)0.0071 (14)
C140.0427 (19)0.051 (2)0.056 (2)0.0100 (16)0.0009 (16)0.0150 (17)
C150.051 (2)0.042 (2)0.080 (3)0.0060 (17)0.008 (2)0.0092 (19)
C160.061 (2)0.039 (2)0.069 (3)0.0096 (17)0.015 (2)0.0046 (17)
C170.0501 (19)0.0382 (18)0.0492 (19)0.0160 (15)0.0083 (15)0.0032 (14)
C180.0361 (16)0.0390 (17)0.0393 (16)0.0160 (13)0.0044 (12)0.0033 (13)
C190.073 (3)0.051 (2)0.046 (2)0.023 (2)0.0084 (18)0.0137 (17)
C200.065 (2)0.056 (2)0.0388 (18)0.0210 (19)0.0064 (16)0.0014 (16)
C210.0429 (18)0.0479 (19)0.0370 (16)0.0186 (15)0.0027 (13)0.0035 (14)
C220.0432 (19)0.065 (2)0.049 (2)0.0075 (18)0.0042 (16)0.0072 (18)
C230.046 (2)0.056 (2)0.059 (2)0.0172 (17)0.0110 (18)0.0104 (19)
C240.0369 (16)0.053 (2)0.0337 (15)0.0106 (14)0.0017 (12)0.0007 (14)
C250.049 (2)0.065 (3)0.051 (2)0.0095 (18)0.0009 (16)0.0199 (18)
C260.074 (3)0.090 (3)0.065 (3)0.040 (3)0.008 (2)0.022 (2)
C270.053 (3)0.126 (5)0.061 (3)0.043 (3)0.010 (2)0.004 (3)
C280.038 (2)0.111 (4)0.071 (3)0.005 (2)0.0018 (19)0.003 (3)
C290.051 (2)0.058 (2)0.058 (2)0.0036 (18)0.0050 (18)0.0093 (18)
C300.0304 (15)0.0446 (18)0.0461 (18)0.0068 (13)0.0026 (13)0.0013 (14)
C310.080 (3)0.056 (2)0.052 (2)0.022 (2)0.016 (2)0.0096 (18)
C320.096 (4)0.055 (3)0.068 (3)0.034 (2)0.003 (2)0.009 (2)
C330.085 (3)0.061 (3)0.075 (3)0.042 (2)0.003 (2)0.010 (2)
C340.080 (3)0.077 (3)0.058 (2)0.040 (3)0.013 (2)0.006 (2)
C350.061 (2)0.060 (2)0.047 (2)0.0256 (19)0.0108 (17)0.0061 (17)
C360.0414 (17)0.0419 (18)0.0479 (19)0.0112 (14)0.0106 (14)0.0045 (15)
C370.057 (2)0.050 (2)0.067 (3)0.0063 (18)0.0139 (19)0.0097 (19)
C380.059 (2)0.046 (2)0.084 (3)0.0054 (19)0.026 (2)0.003 (2)
C390.071 (3)0.045 (2)0.078 (3)0.022 (2)0.034 (2)0.023 (2)
C400.056 (2)0.049 (2)0.050 (2)0.0235 (17)0.0179 (17)0.0104 (16)
C410.0428 (17)0.0364 (17)0.0422 (17)0.0155 (14)0.0128 (14)0.0056 (13)
C420.075 (3)0.071 (3)0.048 (2)0.031 (2)0.012 (2)0.0167 (19)
C430.072 (3)0.086 (3)0.0362 (19)0.034 (2)0.0040 (18)0.0023 (19)
C440.051 (2)0.062 (2)0.0389 (18)0.0239 (18)0.0021 (15)0.0044 (16)
C450.058 (2)0.077 (3)0.054 (2)0.013 (2)0.0075 (19)0.019 (2)
C460.051 (2)0.067 (3)0.053 (2)0.0124 (19)0.0006 (18)0.019 (2)
Geometric parameters (Å, º) top
Sn1—O12.019 (2)C17—C181.398 (5)
Sn1—C12.121 (3)C17—C191.415 (5)
Sn1—C72.122 (3)C19—C201.354 (6)
Sn1—N22.257 (3)C19—H19A0.9300
Sn1—N12.348 (3)C20—C211.410 (5)
Sn2—O22.015 (2)C20—H20A0.9300
Sn2—C302.119 (3)C21—C221.494 (5)
Sn2—C242.122 (3)C22—H22A0.9600
Sn2—N42.227 (4)C22—H22B0.9600
Sn2—N32.341 (3)C22—H22C0.9600
S1—C231.631 (5)C24—C251.380 (5)
S2—C461.634 (5)C24—C291.392 (5)
O1—C131.343 (4)C25—C261.380 (6)
O2—C361.338 (4)C25—H25A0.9300
N1—C211.329 (4)C26—C271.367 (7)
N1—C181.362 (4)C26—H26A0.9300
N2—C231.046 (5)C27—C281.352 (7)
N3—C441.332 (4)C27—H27A0.9300
N3—C411.356 (4)C28—C291.394 (6)
N4—C461.059 (5)C28—H28A0.9300
C1—C61.378 (5)C29—H29A0.9300
C1—C21.390 (5)C30—C351.387 (5)
C2—C31.387 (5)C30—C311.383 (5)
C2—H2A0.9300C31—C321.367 (6)
C3—C41.370 (6)C31—H31A0.9300
C3—H3A0.9300C32—C331.346 (7)
C4—C51.363 (6)C32—H32A0.9300
C4—H4A0.9300C33—C341.363 (6)
C5—C61.392 (5)C33—H33A0.9300
C5—H5A0.9300C34—C351.366 (6)
C6—H6A0.9300C34—H34A0.9300
C7—C121.389 (5)C35—H35A0.9300
C7—C81.392 (5)C36—C371.379 (5)
C8—C91.384 (6)C36—C411.419 (5)
C8—H8A0.9300C37—C381.403 (6)
C9—C101.361 (6)C37—H37A0.9300
C9—H9A0.9300C38—C391.340 (7)
C10—C111.370 (5)C38—H38A0.9300
C10—H10A0.9300C39—C401.409 (6)
C11—C121.379 (5)C39—H39A0.9300
C11—H11A0.9300C40—C421.412 (6)
C12—H12A0.9300C40—C411.413 (5)
C13—C141.367 (5)C42—C431.336 (7)
C13—C181.430 (4)C42—H42A0.9300
C14—C151.413 (6)C43—C441.422 (5)
C14—H14A0.9300C43—H43A0.9300
C15—C161.352 (6)C44—C451.478 (6)
C15—H15A0.9300C45—H45A0.9600
C16—C171.410 (5)C45—H45B0.9600
C16—H16A0.9300C45—H45C0.9600
O1—Sn1—C1109.54 (11)C20—C19—H19A119.7
O1—Sn1—C7111.63 (11)C17—C19—H19A119.7
C1—Sn1—C7138.77 (12)C19—C20—C21120.3 (3)
O1—Sn1—N283.88 (12)C19—C20—H20A119.8
C1—Sn1—N292.22 (12)C21—C20—H20A119.8
C7—Sn1—N294.25 (13)N1—C21—C20120.1 (3)
O1—Sn1—N175.77 (9)N1—C21—C22119.5 (3)
C1—Sn1—N194.66 (10)C20—C21—C22120.3 (3)
C7—Sn1—N193.13 (11)C21—C22—H22A109.5
N2—Sn1—N1159.65 (12)C21—C22—H22B109.5
O2—Sn2—C30114.60 (12)H22A—C22—H22B109.5
O2—Sn2—C24111.83 (12)C21—C22—H22C109.5
C30—Sn2—C24133.47 (13)H22A—C22—H22C109.5
O2—Sn2—N482.33 (12)H22B—C22—H22C109.5
C30—Sn2—N495.46 (13)N2—C23—S1174.0 (4)
C24—Sn2—N493.36 (12)C25—C24—C29119.2 (3)
O2—Sn2—N375.56 (10)C25—C24—Sn2117.1 (3)
C30—Sn2—N394.26 (11)C29—C24—Sn2123.7 (3)
C24—Sn2—N394.28 (11)C24—C25—C26120.7 (4)
N4—Sn2—N3157.88 (13)C24—C25—H25A119.7
C13—O1—Sn1119.2 (2)C26—C25—H25A119.7
C36—O2—Sn2119.2 (2)C27—C26—C25119.7 (4)
C21—N1—C18120.1 (3)C27—C26—H26A120.2
C21—N1—Sn1131.2 (2)C25—C26—H26A120.2
C18—N1—Sn1108.61 (19)C28—C27—C26120.6 (4)
C23—N2—Sn1143.4 (3)C28—C27—H27A119.7
C44—N3—C41120.6 (3)C26—C27—H27A119.7
C44—N3—Sn2130.4 (3)C27—C28—C29120.9 (4)
C41—N3—Sn2108.9 (2)C27—C28—H28A119.6
C46—N4—Sn2161.1 (4)C29—C28—H28A119.6
C6—C1—C2118.8 (3)C24—C29—C28118.9 (4)
C6—C1—Sn1124.8 (2)C24—C29—H29A120.5
C2—C1—Sn1116.4 (2)C28—C29—H29A120.5
C3—C2—C1120.3 (4)C35—C30—C31117.8 (3)
C3—C2—H2A119.8C35—C30—Sn2121.4 (3)
C1—C2—H2A119.8C31—C30—Sn2120.7 (3)
C4—C3—C2120.6 (4)C32—C31—C30121.0 (4)
C4—C3—H3A119.7C32—C31—H31A119.5
C2—C3—H3A119.7C30—C31—H31A119.5
C5—C4—C3119.2 (3)C33—C32—C31120.4 (4)
C5—C4—H4A120.4C33—C32—H32A119.8
C3—C4—H4A120.4C31—C32—H32A119.8
C4—C5—C6121.3 (4)C32—C33—C34119.8 (4)
C4—C5—H5A119.4C32—C33—H33A120.1
C6—C5—H5A119.4C34—C33—H33A120.1
C1—C6—C5119.9 (3)C35—C34—C33120.9 (4)
C1—C6—H6A120.1C35—C34—H34A119.5
C5—C6—H6A120.1C33—C34—H34A119.5
C12—C7—C8118.0 (3)C34—C35—C30120.1 (4)
C12—C7—Sn1121.5 (2)C34—C35—H35A120.0
C8—C7—Sn1120.2 (3)C30—C35—H35A120.0
C9—C8—C7120.1 (4)O2—C36—C37122.3 (3)
C9—C8—H8A120.0O2—C36—C41119.2 (3)
C7—C8—H8A120.0C37—C36—C41118.5 (3)
C10—C9—C8121.0 (4)C36—C37—C38120.2 (4)
C10—C9—H9A119.5C36—C37—H37A119.9
C8—C9—H9A119.5C38—C37—H37A119.9
C9—C10—C11119.7 (4)C39—C38—C37122.0 (4)
C9—C10—H10A120.1C39—C38—H38A119.0
C11—C10—H10A120.1C37—C38—H38A119.0
C10—C11—C12120.2 (4)C38—C39—C40120.2 (4)
C10—C11—H11A119.9C38—C39—H39A119.9
C12—C11—H11A119.9C40—C39—H39A119.9
C11—C12—C7121.0 (3)C42—C40—C39126.0 (4)
C11—C12—H12A119.5C42—C40—C41115.4 (4)
C7—C12—H12A119.5C39—C40—C41118.6 (4)
O1—C13—C14122.5 (3)N3—C41—C40122.8 (3)
O1—C13—C18118.8 (3)N3—C41—C36116.7 (3)
C14—C13—C18118.7 (3)C40—C41—C36120.5 (3)
C13—C14—C15120.3 (4)C43—C42—C40121.2 (4)
C13—C14—H14A119.8C43—C42—H42A119.4
C15—C14—H14A119.8C40—C42—H42A119.4
C16—C15—C14121.5 (4)C42—C43—C44121.1 (4)
C16—C15—H15A119.2C42—C43—H43A119.5
C14—C15—H15A119.2C44—C43—H43A119.5
C15—C16—C17119.8 (4)N3—C44—C43118.9 (4)
C15—C16—H16A120.1N3—C44—C45119.4 (3)
C17—C16—H16A120.1C43—C44—C45121.7 (4)
C18—C17—C16119.4 (3)C44—C45—H45A109.5
C18—C17—C19116.0 (3)C44—C45—H45B109.5
C16—C17—C19124.7 (3)H45A—C45—H45B109.5
N1—C18—C17122.9 (3)C44—C45—H45C109.5
N1—C18—C13116.9 (3)H45A—C45—H45C109.5
C17—C18—C13120.2 (3)H45B—C45—H45C109.5
C20—C19—C17120.7 (3)N4—C46—S2177.4 (4)
C1—Sn1—O1—C1397.4 (2)C19—C17—C18—N10.6 (5)
C7—Sn1—O1—C1380.2 (2)C16—C17—C18—C130.8 (5)
N2—Sn1—O1—C13172.4 (2)C19—C17—C18—C13179.7 (3)
N1—Sn1—O1—C137.5 (2)O1—C13—C18—N11.9 (4)
C30—Sn2—O2—C3682.1 (3)C14—C13—C18—N1177.8 (3)
C24—Sn2—O2—C3694.8 (3)O1—C13—C18—C17179.0 (3)
N4—Sn2—O2—C36174.6 (3)C14—C13—C18—C171.3 (5)
N3—Sn2—O2—C366.0 (2)C18—C17—C19—C200.2 (5)
O1—Sn1—N1—C21178.9 (3)C16—C17—C19—C20178.5 (4)
C1—Sn1—N1—C2170.0 (3)C17—C19—C20—C210.2 (6)
C7—Sn1—N1—C2169.5 (3)C18—N1—C21—C200.2 (5)
N2—Sn1—N1—C21179.3 (3)Sn1—N1—C21—C20174.4 (2)
O1—Sn1—N1—C185.97 (19)C18—N1—C21—C22178.9 (3)
C1—Sn1—N1—C18115.0 (2)Sn1—N1—C21—C224.3 (5)
C7—Sn1—N1—C18105.6 (2)C19—C20—C21—N10.2 (6)
N2—Sn1—N1—C185.6 (4)C19—C20—C21—C22178.5 (4)
O1—Sn1—N2—C23130.5 (6)O2—Sn2—C24—C2514.3 (3)
C1—Sn1—N2—C2321.1 (6)C30—Sn2—C24—C25169.6 (3)
C7—Sn1—N2—C23118.2 (6)N4—Sn2—C24—C2568.8 (3)
N1—Sn1—N2—C23130.9 (6)N3—Sn2—C24—C2590.4 (3)
O2—Sn2—N3—C44177.8 (3)O2—Sn2—C24—C29167.0 (3)
C30—Sn2—N3—C4467.9 (3)C30—Sn2—C24—C299.2 (4)
C24—Sn2—N3—C4466.4 (3)N4—Sn2—C24—C29110.0 (3)
N4—Sn2—N3—C44176.2 (3)N3—Sn2—C24—C2990.8 (3)
O2—Sn2—N3—C414.5 (2)C29—C24—C25—C260.9 (6)
C30—Sn2—N3—C41109.9 (2)Sn2—C24—C25—C26178.0 (3)
C24—Sn2—N3—C41115.9 (2)C24—C25—C26—C271.3 (7)
N4—Sn2—N3—C416.1 (4)C25—C26—C27—C280.6 (8)
O2—Sn2—N4—C46144.9 (11)C26—C27—C28—C290.4 (8)
C30—Sn2—N4—C4630.8 (11)C25—C24—C29—C280.1 (6)
C24—Sn2—N4—C46103.5 (11)Sn2—C24—C29—C28178.9 (3)
N3—Sn2—N4—C46146.5 (10)C27—C28—C29—C240.8 (7)
O1—Sn1—C1—C6156.6 (3)O2—Sn2—C30—C3565.5 (3)
C7—Sn1—C1—C620.0 (4)C24—Sn2—C30—C35110.6 (3)
N2—Sn1—C1—C6119.1 (3)N4—Sn2—C30—C35149.5 (3)
N1—Sn1—C1—C680.1 (3)N3—Sn2—C30—C3510.6 (3)
O1—Sn1—C1—C222.7 (3)O2—Sn2—C30—C31111.5 (3)
C7—Sn1—C1—C2160.7 (3)C24—Sn2—C30—C3172.4 (4)
N2—Sn1—C1—C261.6 (3)N4—Sn2—C30—C3127.5 (3)
N1—Sn1—C1—C299.2 (3)N3—Sn2—C30—C31172.4 (3)
C6—C1—C2—C30.8 (6)C35—C30—C31—C320.0 (6)
Sn1—C1—C2—C3178.5 (3)Sn2—C30—C31—C32177.1 (4)
C1—C2—C3—C40.1 (6)C30—C31—C32—C331.4 (8)
C2—C3—C4—C50.9 (7)C31—C32—C33—C343.0 (8)
C3—C4—C5—C60.8 (6)C32—C33—C34—C353.2 (8)
C2—C1—C6—C51.0 (5)C33—C34—C35—C301.8 (7)
Sn1—C1—C6—C5178.3 (3)C31—C30—C35—C340.2 (6)
C4—C5—C6—C10.2 (6)Sn2—C30—C35—C34177.3 (3)
O1—Sn1—C7—C1272.3 (3)Sn2—O2—C36—C37173.4 (3)
C1—Sn1—C7—C12104.4 (3)Sn2—O2—C36—C416.8 (4)
N2—Sn1—C7—C12157.4 (3)O2—C36—C37—C38179.5 (4)
N1—Sn1—C7—C123.7 (3)C41—C36—C37—C380.2 (6)
O1—Sn1—C7—C8101.7 (3)C36—C37—C38—C390.5 (7)
C1—Sn1—C7—C881.7 (3)C37—C38—C39—C400.3 (7)
N2—Sn1—C7—C816.6 (3)C38—C39—C40—C42179.6 (4)
N1—Sn1—C7—C8177.6 (3)C38—C39—C40—C410.7 (6)
C12—C7—C8—C91.9 (6)C44—N3—C41—C401.3 (5)
Sn1—C7—C8—C9172.3 (3)Sn2—N3—C41—C40176.7 (3)
C7—C8—C9—C101.2 (7)C44—N3—C41—C36179.4 (3)
C8—C9—C10—C110.3 (8)Sn2—N3—C41—C362.6 (3)
C9—C10—C11—C120.2 (7)C42—C40—C41—N31.2 (5)
C10—C11—C12—C70.9 (6)C39—C40—C41—N3177.8 (3)
C8—C7—C12—C111.8 (5)C42—C40—C41—C36179.5 (3)
Sn1—C7—C12—C11172.3 (3)C39—C40—C41—C361.5 (5)
Sn1—O1—C13—C14171.6 (3)O2—C36—C41—N32.2 (5)
Sn1—O1—C13—C188.1 (4)C37—C36—C41—N3178.1 (3)
O1—C13—C14—C15179.8 (3)O2—C36—C41—C40178.5 (3)
C18—C13—C14—C150.5 (5)C37—C36—C41—C401.2 (5)
C13—C14—C15—C160.7 (6)C39—C40—C42—C43178.8 (4)
C14—C15—C16—C171.2 (6)C41—C40—C42—C430.2 (6)
C15—C16—C17—C180.4 (6)C40—C42—C43—C440.8 (7)
C15—C16—C17—C19178.3 (4)C41—N3—C44—C430.3 (5)
C21—N1—C18—C170.6 (5)Sn2—N3—C44—C43177.2 (3)
Sn1—N1—C18—C17175.1 (3)C41—N3—C44—C45179.9 (3)
C21—N1—C18—C13179.7 (3)Sn2—N3—C44—C452.5 (5)
Sn1—N1—C18—C134.0 (3)C42—C43—C44—N30.8 (6)
C16—C17—C18—N1178.2 (3)C42—C43—C44—C45178.9 (4)

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2(C10H8NO)(NCS)]
Mr489.14
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.0093 (5), 11.5809 (6), 20.5129 (11)
α, β, γ (°)83.7166 (7), 85.4123 (7), 78.2441 (7)
V3)2079.09 (19)
Z4
Radiation typeMo Kα
µ (mm1)1.35
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.615, 0.775
No. of measured, independent and
observed [I > 2σ(I)] reflections
19942, 9461, 7796
Rint0.021
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.103, 1.04
No. of reflections9461
No. of parameters507
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.96

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

 

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLinden, A., Basu Baul, T. S. & Mizar, A. (2005). Acta Cryst. E61, m27–m29.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNg, S. W. (1999). J. Organomet. Chem. 585, 12–17.  Web of Science CSD CrossRef CAS 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 citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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