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The reaction of pyrazine-2-carbaldehyde 4-ethyl­thio­semi­carbazone (Hapetsc) with diphenyl­tin(IV) dichloride in ethanol resulted in the formation of the title compound, dichloridodiphenyl­bis(pyrazine-2-carbaldehyde 4-ethyl­thio­semi­carbazone)tin(IV), [Sn(C6H5)2Cl2(C9H13N5S)2]. The complex exhibits a distorted octa­hedron about the Sn atom, which lies on an inversion center and is coordinated by two Cl atoms, two phenyl ligands and two Hapetsc units. The pyrazine ligands are in a trans configuration and behave as monodentate donors through their ring N atoms. The Sn-Cl distances are 2.5484 (4) Å, the Sn-C distances are 2.1378 (12) Å and the Sn-N distances are 2.4032 (11) Å. One NH group of the thio­semicarbazone ligand forms an intra­molecular S(5) hydrogen bond with an adjacent N atom on the same ligand. The other N-H group is not involved in hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035052/rz2159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035052/rz2159Isup2.hkl
Contains datablock I

CCDC reference: 657627

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 34.9

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Comment top

There has been a steady growth of interest in the synthesis, structure and reactivity studies of metal complexes of heterocyclic thiosemicarbazones due to their biological and pharmacological properties (Ali & Livingstone, 1974; Campbell, 1975; Padhye & Kauffman, 1985). The unique feature is attributed to the tautomeric equilibrium present in the thiosemicarbazone moiety and thereby the coordinating ability with many metal ions. Among the non-transition metals, organotin(IV) derivatives are of special interest due to environmental, and medical issues (Barbieri et al., 1993; Bamgboye & Bamgboye, 1988; Casas et al., 1994, Casas et al., 1996, De Sousa et al., 2001). Continuing with this type of studies, we describe here the structure of a diphenyltin dichloride derivative of pyrazine-2-carbaldehyde N(4)-ethyl-3-thiosemicarbazone (I).

The tin atom of the diphenyl dichloride unit lies on an inversion center, and is coordinated in monodentate fashion by the pyrazine nitrogen atoms of two thiosemicarbazone ligands, unlike the normal bidentate/tridentate modes of coordination. The yellow-colored complex is built up of discrete molecules of acetylpyrazine thiosemicarbazone ligand with diphenyl tin dichloride with the two chlorine atoms and two phenyl groups occupying the four equatorial positions (trans to each other) of a distorted octahedron around the tin atom. The pyrazine groups are in the inverse position and trans to one another. The angles subtended by the adjacent atoms to tin are 89.75 (4)°, [C10—Sn—Cl1], 88.99 (4)° [N1—Sn1—C10] and 91.79 (3)° (N1—Sn1—Cl1] and the corresponding bond distances are Sn—C [2.1378 (12)], Sn—Cl [2.5483 (4)] and Sn—N [2.4033 (11) Å]. The Sn—N bond length value is in the range of 2.27 to 2.58, and is less than the van der Waals radii of the two atoms, 3.74 Å (Allen et al., 1979). The Sn—Cl bond is in the range of normal covalent radii (2.37–2.60 Å) (Casas et al., 1997, Davies, 1998). The bond length Sn—C (phenyl) is slightly shorter compared to the tin adduct reported 2.1424 (14) Å by us earlier (Venkatraman et al., 2004). The bond length Sn—C increases with an increase in coordination number from four [2.122 (11) Å] (in Ph2SnCl2) and higher as expected (Dey et al., 2003).

N–H groups usually serve as hydrogen-bond donors, however, no intermolecular hyrogen bonding is present in this structure. N–H group N5 forms an intramolecular hydrogen bond of graph set designation S(5) (Etter, 1990), with N3 as acceptor, N3···N5 2.609 (2) Å. In five-membered rings, the hydrogen-bonding geometry necessarily distorts greatly from linearity. The H···N3 distance is 2.15 (2) Å, and the angle about H is 109.9 (19)°. The other N–H group N4 is not involved in hydrogen bonding.

Related literature top

For related literature, see: Ali & Livingstone (1974); Allen et al. (1979); Bamgboye & Bamgboye (1988); Barbieri et al. (1993); Campbell (1975); Casas et al. (1994, 1996, 1997); Davies (1998); De Sousa, Francisco, Gambardella, Santos & Abras (2001); Dey et al. (2003); Etter (1990); Padhye & Kauffman (1985); Venkatraman et al. (2004).

Experimental top

The tin complex of acetylpyrazine N(4)-ethylthiosemicarbazone was prepared by the following procedure: a solution of diphenyltin dichloride (0.69 g, 2 mmol) in 20 ml of dry methanol was added to a refluxing methanol solution (20 ml) of the ligand. The resulting mixture was refluxed for 1 h. Cooling followed by slow evaporation at room temperature produced yellow crystals (ca 75% yield), with a melting point 459–461 K. IR spectra were obtained in the 4000–400 cm-1 range in KBr pellets on a Nicolet 670 F T—IR spectrophotometer νN—H 3350, νC—N 1590, 1530(s), νC—S 850(s) cm-1).

Refinement top

H atoms on C were placed in idealized positions with C—H distances 0.95–0.99 Å and thereafter treated as riding. Uiso for H was assigned as 1.2 times Ueq of the attached C or N atoms (1.5 for methyl). A torsional parameter was refined for each methyl group. N—H hydrogen atom positions were refined.

Structure description top

There has been a steady growth of interest in the synthesis, structure and reactivity studies of metal complexes of heterocyclic thiosemicarbazones due to their biological and pharmacological properties (Ali & Livingstone, 1974; Campbell, 1975; Padhye & Kauffman, 1985). The unique feature is attributed to the tautomeric equilibrium present in the thiosemicarbazone moiety and thereby the coordinating ability with many metal ions. Among the non-transition metals, organotin(IV) derivatives are of special interest due to environmental, and medical issues (Barbieri et al., 1993; Bamgboye & Bamgboye, 1988; Casas et al., 1994, Casas et al., 1996, De Sousa et al., 2001). Continuing with this type of studies, we describe here the structure of a diphenyltin dichloride derivative of pyrazine-2-carbaldehyde N(4)-ethyl-3-thiosemicarbazone (I).

The tin atom of the diphenyl dichloride unit lies on an inversion center, and is coordinated in monodentate fashion by the pyrazine nitrogen atoms of two thiosemicarbazone ligands, unlike the normal bidentate/tridentate modes of coordination. The yellow-colored complex is built up of discrete molecules of acetylpyrazine thiosemicarbazone ligand with diphenyl tin dichloride with the two chlorine atoms and two phenyl groups occupying the four equatorial positions (trans to each other) of a distorted octahedron around the tin atom. The pyrazine groups are in the inverse position and trans to one another. The angles subtended by the adjacent atoms to tin are 89.75 (4)°, [C10—Sn—Cl1], 88.99 (4)° [N1—Sn1—C10] and 91.79 (3)° (N1—Sn1—Cl1] and the corresponding bond distances are Sn—C [2.1378 (12)], Sn—Cl [2.5483 (4)] and Sn—N [2.4033 (11) Å]. The Sn—N bond length value is in the range of 2.27 to 2.58, and is less than the van der Waals radii of the two atoms, 3.74 Å (Allen et al., 1979). The Sn—Cl bond is in the range of normal covalent radii (2.37–2.60 Å) (Casas et al., 1997, Davies, 1998). The bond length Sn—C (phenyl) is slightly shorter compared to the tin adduct reported 2.1424 (14) Å by us earlier (Venkatraman et al., 2004). The bond length Sn—C increases with an increase in coordination number from four [2.122 (11) Å] (in Ph2SnCl2) and higher as expected (Dey et al., 2003).

N–H groups usually serve as hydrogen-bond donors, however, no intermolecular hyrogen bonding is present in this structure. N–H group N5 forms an intramolecular hydrogen bond of graph set designation S(5) (Etter, 1990), with N3 as acceptor, N3···N5 2.609 (2) Å. In five-membered rings, the hydrogen-bonding geometry necessarily distorts greatly from linearity. The H···N3 distance is 2.15 (2) Å, and the angle about H is 109.9 (19)°. The other N–H group N4 is not involved in hydrogen bonding.

For related literature, see: Ali & Livingstone (1974); Allen et al. (1979); Bamgboye & Bamgboye (1988); Barbieri et al. (1993); Campbell (1975); Casas et al. (1994, 1996, 1997); Davies (1998); De Sousa, Francisco, Gambardella, Santos & Abras (2001); Dey et al. (2003); Etter (1990); Padhye & Kauffman (1985); Venkatraman et al. (2004).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Numbering scheme and displacement ellipsoids at the 50% level. H atoms are represented with arbitrary radius. Unlabelled atoms are related by the symmetry operation (1 - x, 1 - y, 1 - z).
dichloridodiphenylbis(pyrazine-2-carbaldehyde 4-ethylthiosemicarbazone)tin(IV) top
Crystal data top
[Sn(C6H5)2Cl2(C9H13N5S)2]F(000) = 804
Mr = 790.40Dx = 1.591 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6430 reflections
a = 10.7262 (15) Åθ = 2.5–35.6°
b = 17.971 (3) ŵ = 1.10 mm1
c = 9.0868 (13) ÅT = 90 K
β = 109.641 (6)°Needle fragment, yellow
V = 1649.7 (4) Å30.27 × 0.22 × 0.20 mm
Z = 2
Data collection top
Nonius KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
7475 independent reflections
Radiation source: fine-focus sealed tube6422 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scans with κ offsetsθmax = 35.6°, θmin = 2.7°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 1717
Tmin = 0.755, Tmax = 0.810k = 2529
24456 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0301P)2 + 1.1288P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7475 reflectionsΔρmax = 0.85 e Å3
214 parametersΔρmin = 1.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (4)
Crystal data top
[Sn(C6H5)2Cl2(C9H13N5S)2]V = 1649.7 (4) Å3
Mr = 790.40Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.7262 (15) ŵ = 1.10 mm1
b = 17.971 (3) ÅT = 90 K
c = 9.0868 (13) Å0.27 × 0.22 × 0.20 mm
β = 109.641 (6)°
Data collection top
Nonius KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
7475 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
6422 reflections with I > 2σ(I)
Tmin = 0.755, Tmax = 0.810Rint = 0.026
24456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.85 e Å3
7475 reflectionsΔρmin = 1.29 e Å3
214 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.50000.50000.00677 (3)
Cl10.42470 (3)0.606662 (17)0.63487 (3)0.01054 (6)
S10.15561 (4)0.75620 (2)0.60254 (4)0.01438 (7)
N10.27549 (11)0.46903 (6)0.34850 (13)0.00969 (18)
N20.00894 (12)0.45016 (7)0.16677 (14)0.0129 (2)
N30.01068 (11)0.59622 (6)0.42005 (13)0.01122 (19)
N40.09760 (11)0.64282 (7)0.45362 (14)0.01177 (19)
H4N0.176 (2)0.6485 (12)0.391 (2)0.014*
N50.07887 (12)0.68918 (7)0.65242 (15)0.0152 (2)
H5N0.123 (2)0.6529 (13)0.620 (3)0.018*
C10.18071 (13)0.51177 (7)0.36914 (16)0.0111 (2)
H10.20440.54950.44680.013*
C20.23751 (13)0.41575 (8)0.23804 (16)0.0121 (2)
H20.30200.38370.22140.015*
C30.10492 (14)0.40721 (8)0.14829 (16)0.0137 (2)
H30.08130.36940.07070.016*
C40.04715 (13)0.50219 (7)0.27881 (15)0.00994 (19)
C50.05560 (13)0.55018 (7)0.30524 (15)0.0105 (2)
C60.19717 (13)0.54186 (8)0.20520 (17)0.0146 (2)
H6A0.24950.52670.27010.022*
H6B0.20450.50400.12510.022*
H6C0.23040.58950.15470.022*
C70.04970 (13)0.69445 (7)0.57094 (15)0.0115 (2)
C80.14983 (16)0.73660 (10)0.78438 (18)0.0208 (3)
H8A0.21950.70700.86150.025*
H8B0.08750.75440.83600.025*
C90.21281 (19)0.80299 (11)0.7342 (2)0.0301 (4)
H9A0.27160.78570.67880.045*
H9B0.26410.83160.82660.045*
H9C0.14350.83470.66470.045*
C100.50493 (12)0.57431 (7)0.31832 (14)0.00910 (19)
C110.56171 (13)0.64482 (7)0.35463 (15)0.0107 (2)
H110.59830.65990.46070.013*
C120.56497 (14)0.69314 (8)0.23604 (16)0.0137 (2)
H120.60540.74060.26160.016*
C130.50916 (14)0.67200 (8)0.08006 (16)0.0140 (2)
H130.51040.70520.00070.017*
C140.45164 (14)0.60209 (8)0.04319 (15)0.0130 (2)
H140.41300.58770.06310.016*
C150.45039 (13)0.55302 (7)0.16182 (15)0.0109 (2)
H150.41230.50500.13600.013*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.00730 (5)0.00772 (5)0.00631 (5)0.00094 (4)0.00365 (3)0.00064 (4)
Cl10.01262 (12)0.01062 (12)0.00942 (11)0.00198 (10)0.00508 (9)0.00091 (9)
S10.01682 (15)0.01227 (14)0.01643 (14)0.00014 (11)0.00872 (12)0.00298 (11)
N10.0089 (4)0.0106 (4)0.0103 (4)0.0001 (3)0.0041 (3)0.0003 (3)
N20.0121 (5)0.0136 (5)0.0128 (5)0.0004 (4)0.0039 (4)0.0032 (4)
N30.0109 (4)0.0112 (4)0.0123 (4)0.0007 (4)0.0049 (4)0.0014 (4)
N40.0098 (4)0.0125 (5)0.0130 (5)0.0012 (4)0.0038 (4)0.0025 (4)
N50.0126 (5)0.0169 (5)0.0145 (5)0.0002 (4)0.0025 (4)0.0044 (4)
C10.0097 (5)0.0118 (5)0.0122 (5)0.0002 (4)0.0042 (4)0.0017 (4)
C20.0110 (5)0.0130 (5)0.0131 (5)0.0006 (4)0.0049 (4)0.0017 (4)
C30.0134 (5)0.0137 (5)0.0140 (5)0.0002 (4)0.0046 (4)0.0040 (4)
C40.0085 (5)0.0112 (5)0.0107 (5)0.0003 (4)0.0041 (4)0.0006 (4)
C50.0088 (5)0.0113 (5)0.0118 (5)0.0003 (4)0.0038 (4)0.0006 (4)
C60.0085 (5)0.0168 (6)0.0174 (6)0.0003 (4)0.0028 (4)0.0041 (5)
C70.0136 (5)0.0115 (5)0.0108 (5)0.0015 (4)0.0059 (4)0.0004 (4)
C80.0179 (6)0.0256 (7)0.0158 (6)0.0010 (6)0.0014 (5)0.0078 (5)
C90.0241 (8)0.0331 (9)0.0333 (9)0.0137 (7)0.0102 (7)0.0156 (8)
C100.0095 (5)0.0102 (5)0.0087 (5)0.0006 (4)0.0045 (4)0.0014 (4)
C110.0112 (5)0.0103 (5)0.0119 (5)0.0003 (4)0.0053 (4)0.0007 (4)
C120.0156 (6)0.0120 (5)0.0154 (6)0.0008 (4)0.0076 (5)0.0022 (4)
C130.0155 (6)0.0154 (6)0.0130 (5)0.0010 (5)0.0072 (4)0.0049 (4)
C140.0147 (5)0.0163 (6)0.0089 (5)0.0000 (5)0.0051 (4)0.0018 (4)
C150.0117 (5)0.0127 (5)0.0088 (5)0.0007 (4)0.0043 (4)0.0006 (4)
Geometric parameters (Å, º) top
Sn1—C10i2.1378 (12)C4—C51.4813 (18)
Sn1—C102.1378 (12)C5—C61.4921 (19)
Sn1—N1i2.4032 (11)C6—H6A0.9800
Sn1—N12.4033 (11)C6—H6B0.9800
Sn1—Cl1i2.5483 (4)C6—H6C0.9800
Sn1—Cl12.5483 (4)C8—C91.515 (3)
S1—C71.6804 (14)C8—H8A0.9900
N1—C11.3367 (17)C8—H8B0.9900
N1—C21.3473 (17)C9—H9A0.9800
N2—C41.3411 (17)C9—H9B0.9800
N2—C31.3416 (18)C9—H9C0.9800
N3—C51.2912 (17)C10—C111.3966 (18)
N3—N41.3619 (16)C10—C151.3971 (18)
N4—C71.3759 (17)C11—C121.3934 (18)
N4—H4N0.85 (2)C11—H110.9500
N5—C71.3314 (18)C12—C131.393 (2)
N5—C81.4593 (19)C12—H120.9500
N5—H5N0.91 (2)C13—C141.390 (2)
C1—C41.4019 (18)C13—H130.9500
C1—H10.9500C14—C151.3963 (18)
C2—C31.3898 (19)C14—H140.9500
C2—H20.9500C15—H150.9500
C3—H30.9500
C10i—Sn1—C10180.0C4—C5—C6120.21 (11)
C10i—Sn1—N1i88.99 (4)C5—C6—H6A109.5
C10—Sn1—N1i91.01 (4)C5—C6—H6B109.5
C10i—Sn1—N191.01 (4)H6A—C6—H6B109.5
C10—Sn1—N188.99 (4)C5—C6—H6C109.5
N1i—Sn1—N1180.0H6A—C6—H6C109.5
C10i—Sn1—Cl1i89.75 (4)H6B—C6—H6C109.5
C10—Sn1—Cl1i90.25 (4)N5—C7—N4115.48 (12)
N1i—Sn1—Cl1i91.79 (3)N5—C7—S1125.82 (11)
N1—Sn1—Cl1i88.21 (3)N4—C7—S1118.68 (10)
C10i—Sn1—Cl190.25 (4)N5—C8—C9112.00 (14)
C10—Sn1—Cl189.75 (4)N5—C8—H8A109.2
N1i—Sn1—Cl188.21 (3)C9—C8—H8A109.2
N1—Sn1—Cl191.79 (3)N5—C8—H8B109.2
Cl1i—Sn1—Cl1180.0C9—C8—H8B109.2
C1—N1—C2117.33 (11)H8A—C8—H8B107.9
C1—N1—Sn1116.71 (9)C8—C9—H9A109.5
C2—N1—Sn1125.82 (9)C8—C9—H9B109.5
C4—N2—C3116.40 (12)H9A—C9—H9B109.5
C5—N3—N4118.51 (11)C8—C9—H9C109.5
N3—N4—C7118.86 (11)H9A—C9—H9C109.5
N3—N4—H4N121.2 (14)H9B—C9—H9C109.5
C7—N4—H4N118.0 (14)C11—C10—C15119.28 (12)
C7—N5—C8124.90 (13)C11—C10—Sn1120.42 (9)
C7—N5—H5N115.3 (14)C15—C10—Sn1120.29 (9)
C8—N5—H5N119.8 (14)C12—C11—C10120.33 (12)
N1—C1—C4121.53 (12)C12—C11—H11119.8
N1—C1—H1119.2C10—C11—H11119.8
C4—C1—H1119.2C13—C12—C11120.20 (13)
N1—C2—C3120.61 (12)C13—C12—H12119.9
N1—C2—H2119.7C11—C12—H12119.9
C3—C2—H2119.7C14—C13—C12119.72 (12)
N2—C3—C2122.68 (13)C14—C13—H13120.1
N2—C3—H3118.7C12—C13—H13120.1
C2—C3—H3118.7C13—C14—C15120.22 (12)
N2—C4—C1121.43 (12)C13—C14—H14119.9
N2—C4—C5118.35 (11)C15—C14—H14119.9
C1—C4—C5120.21 (12)C14—C15—C10120.23 (12)
N3—C5—C4114.09 (11)C14—C15—H15119.9
N3—C5—C6125.69 (12)C10—C15—H15119.9
C10i—Sn1—N1—C191.62 (10)N2—C4—C5—C62.00 (19)
C10—Sn1—N1—C188.38 (10)C1—C4—C5—C6177.75 (13)
Cl1i—Sn1—N1—C1178.66 (9)C8—N5—C7—N4178.25 (14)
Cl1—Sn1—N1—C11.34 (9)C8—N5—C7—S10.2 (2)
C10i—Sn1—N1—C292.92 (11)N3—N4—C7—N56.22 (18)
C10—Sn1—N1—C287.08 (11)N3—N4—C7—S1175.25 (10)
Cl1i—Sn1—N1—C23.20 (10)C7—N5—C8—C993.44 (18)
Cl1—Sn1—N1—C2176.80 (10)N1i—Sn1—C10—C1143.26 (10)
C5—N3—N4—C7176.94 (12)N1—Sn1—C10—C11136.74 (10)
C2—N1—C1—C40.57 (19)Cl1i—Sn1—C10—C11135.05 (10)
Sn1—N1—C1—C4175.29 (10)Cl1—Sn1—C10—C1144.95 (10)
C1—N1—C2—C31.13 (19)N1i—Sn1—C10—C15137.23 (10)
Sn1—N1—C2—C3174.31 (10)N1—Sn1—C10—C1542.77 (10)
C4—N2—C3—C20.6 (2)Cl1i—Sn1—C10—C1545.44 (10)
N1—C2—C3—N20.5 (2)Cl1—Sn1—C10—C15134.56 (10)
C3—N2—C4—C11.20 (19)C15—C10—C11—C120.57 (19)
C3—N2—C4—C5179.06 (12)Sn1—C10—C11—C12179.92 (10)
N1—C1—C4—N20.6 (2)C10—C11—C12—C131.3 (2)
N1—C1—C4—C5179.63 (12)C11—C12—C13—C140.8 (2)
N4—N3—C5—C4179.97 (11)C12—C13—C14—C150.4 (2)
N4—N3—C5—C61.2 (2)C13—C14—C15—C101.1 (2)
N2—C4—C5—N3176.87 (12)C11—C10—C15—C140.62 (19)
C1—C4—C5—N33.38 (18)Sn1—C10—C15—C14178.90 (10)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···N30.91 (2)2.16 (2)2.6093 (17)109.8 (16)

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2Cl2(C9H13N5S)2]
Mr790.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)10.7262 (15), 17.971 (3), 9.0868 (13)
β (°) 109.641 (6)
V3)1649.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.10
Crystal size (mm)0.27 × 0.22 × 0.20
Data collection
DiffractometerNonius KappaCCD (with Oxford Cryosystems Cryostream cooler)
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.755, 0.810
No. of measured, independent and
observed [I > 2σ(I)] reflections
24456, 7475, 6422
Rint0.026
(sin θ/λ)max1)0.819
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.071, 1.02
No. of reflections7475
No. of parameters214
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.85, 1.29

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···N30.91 (2)2.16 (2)2.6093 (17)109.8 (16)
 

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