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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page m1256
https://doi.org/10.1107/S1600536812038147

Tri­chlorido(di­methyl sulfoxide-κO)(di-2-pyridyl­amine-κ2N,N′)indium(III)

Sadif A. Shirvan,a* Sara Haydari Dezfulia and Elyas Golabib

aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran, and bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
*Correspondence e-mail: sadif_shirvan1@yahoo.com

(Received 29 August 2012; accepted 5 September 2012; online 12 September 2012)

In the title compound, [InCl3(C10H9N3)(C2H6OS)], the InIII atom is six-coordinated in a distorted octa­hedral geometry by two N atoms from a chelating di-2-pyridyl­amine ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. Inter­molecular C—H⋯Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distance = 3.510 (3) Å] are present in the crystal.

Related literature

For related structures, see: Abedi et al. (2011[Abedi, A., Safari, N., Amani, V., Tavajohi, S. & Ostad, N. (2011). Inorg. Chim. Acta, 376, 679-686.], 2012a[Abedi, A., Safari, A. R. & Amani, V. (2012a). Z. Kristallogr. New Cryst. Struct. 227, 169-198.],b[Abedi, A., Safari, N., Amani, V. & Khavasi, H. R. (2012b). J. Coord. Chem. 65, 325-338.]); Ahmadi et al. (2008[Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306-m1307.]); Clemente (2005[Clemente, D. A. (2005). Inorg. Chim. Acta, 358, 1725-1748.]); Dong et al. (1987[Dong, N., Hang, N.-D., Dong, Z.-C. & Hu, S.-Z. (1987). Jiegou Huaxue (Chin. J. Struct. Chem.), 6, 145-149.]); Ilyuhin & Malyarik (1994[Ilyuhin, A. B. & Malyarik, M. A. (1994). Kristallografiya, 39, 439-443.]); Kalateh, Ahmadi et al. (2008[Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353-m1354.]); Kalateh, Norouzi et al. (2008[Kalateh, K., Norouzi, A., Ebadi, A., Ahmadi, R. & Amani, V. (2008). Acta Cryst. E64, m1583-m1584.]); Malecki et al. (2011[Malecki, J. G., Machura, B., Switlicka, A., Gron, T. & Balanda, M. (2011). Polyhedron, 30, 746-753.]); Malyarick et al. (1992[Malyarick, M. A., Petrosyants, S. P. & Ilyuhin, A. B. (1992). Polyhedron, 11, 1067-1073.]); Shi & Jiang (2006[Shi, P.-F. & Jiang, Q. (2006). Acta Cryst. E62, m1183-m1185.]); Shirvan & Haydari Dezfuli (2012[Shirvan, S. A. & Haydari Dezfuli, S. (2012). Acta Cryst. E68, m1189-m1190.]); Yoshikawa et al. (2004[Yoshikawa, N., Sakamoto, J., Kanehisa, N., Kai, Y., Takashima, H. & Tsukahara, K. (2004). Acta Cryst. E60, m546-m547.]); Yousefi et al. (2009[Yousefi, M., Allahgholi Ghasri, M. R., Heidari, A. & Amani, V. (2009). Acta Cryst. E65, m9-m10.]).

[Scheme 1]

Experimental

Crystal data

  • [InCl3(C10H9N3)(C2H6OS)]

  • Mr = 470.51

  • Monoclinic, C 2/c

  • a = 29.283 (2) Å

  • b = 7.7642 (7) Å

  • c = 15.9459 (12) Å

  • β = 104.891 (6)°

  • V = 3503.7 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.93 mm−1

  • T = 298 K

  • 0.20 × 0.18 × 0.15 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.702, Tmax = 0.796

  • 14020 measured reflections

  • 3448 independent reflections

  • 2503 reflections with I > 2σ(I)

  • Rint = 0.075
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.080

  • S = 0.99

  • 3448 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11C⋯Cl2i 0.96 2.74 3.499 (8) 137
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.].

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038147/hy2584sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038147/hy2584Isup2.hkl

checkCIF report


Comment top

Recently, we reported the synthesis and crystal structure of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine). Several InIII complexes with a formula [In(L1)Cl3(L2)] (L1 = an N,N'-chelating ligand, L2 = DMSO, H2O, MeOH or EtOH), such as [In(bipy)Cl3(H2O)], (III), [In(bipy)Cl3(EtOH)], (IV), [In(bipy)Cl3(H2O)].H2O, (V) (Malyarick et al., 1992), [In(phen)Cl3(DMSO)], (VI) (Dong et al., 1987), [In(phen)Cl3(H2O)], (VII), [In(phen)Cl3(EtOH)].EtOH, (VIII) (Ilyuhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl3(DMSO)], (IX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl3(MeOH)], (X) (Kalateh, Ahmadi et al., 2008), [In(4,4'-dtbipy)Cl3(MeOH)].0.5MeOH, (XI) (Abedi et al., 2012a), [In(4bt)Cl3(MeOH)], (XII) and [In(4bt)Cl3(DMSO)], (XIII) (Abedi et al., 2012b) (bipy = 2,2'-bipyridine, phen = 1,10-phenanthroline, DMSO = dimethyl sulfoxide, 4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbipy = 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. Di-2-pyridylamine (DPA) is a good bidentate ligand, and numerous complexes with DPA have been prepared, such as that of [Hg(DPA)Br2], (XIV) (Kalateh, Norouzi et al., 2008), [Hg(DPA)Cl2], (XV) (Yousefi et al., 2009), [Pt(DPA)Cl4].DMF, (XVI) (Abedi et al., 2011), [Ir(DPA)2Cl2](PF6), (XVII) (Yoshikawa et al., 2004), [Cu(DPA)2](BF4)2, (XVIII) (Clemente, 2005), [Mn(DPA)2(NCS)2].0.5H2O, (XIX) (Malecki et al., 2011) and [Au(DPA)Cl2]Cl, (XX) (Shi & Jiang, 2006). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the InIII atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating DPA ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg3···Cg3i [symmetry code: (i) -x, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring], with a centroid–centroid distance of 3.510 (3) Å, stabilize the structure.

Related literature top

For related structures, see: Abedi et al. (2011, 2012a,b); Ahmadi et al. (2008); Clemente (2005); Dong et al. (1987); Ilyuhin & Malyarik (1994); Kalateh, Ahmadi et al. (2008); Kalateh, Norouzi et al. (2008); Malecki et al. (2011); Malyarick et al. (1992); Shi & Jiang (2006); Shirvan & Haydari Dezfuli (2012); Yoshikawa et al. (2004); Yousefi et al. (2009).

Experimental top

For the preparation of the title compound, a solution of di-2-pyridylamine (0.29 g, 1.65 mmol) in methanol (10 ml) was added to a solution of InCl3.4H2O (0.48 g, 1.65 mmol) in methanol (10 ml) at room temperature. The suitable crystals for X-ray diffraction analysis were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.57 g, 73.4%).

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 (CH), 0.96 (CH3) and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N).

Structure description top

Recently, we reported the synthesis and crystal structure of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine). Several InIII complexes with a formula [In(L1)Cl3(L2)] (L1 = an N,N'-chelating ligand, L2 = DMSO, H2O, MeOH or EtOH), such as [In(bipy)Cl3(H2O)], (III), [In(bipy)Cl3(EtOH)], (IV), [In(bipy)Cl3(H2O)].H2O, (V) (Malyarick et al., 1992), [In(phen)Cl3(DMSO)], (VI) (Dong et al., 1987), [In(phen)Cl3(H2O)], (VII), [In(phen)Cl3(EtOH)].EtOH, (VIII) (Ilyuhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl3(DMSO)], (IX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl3(MeOH)], (X) (Kalateh, Ahmadi et al., 2008), [In(4,4'-dtbipy)Cl3(MeOH)].0.5MeOH, (XI) (Abedi et al., 2012a), [In(4bt)Cl3(MeOH)], (XII) and [In(4bt)Cl3(DMSO)], (XIII) (Abedi et al., 2012b) (bipy = 2,2'-bipyridine, phen = 1,10-phenanthroline, DMSO = dimethyl sulfoxide, 4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbipy = 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. Di-2-pyridylamine (DPA) is a good bidentate ligand, and numerous complexes with DPA have been prepared, such as that of [Hg(DPA)Br2], (XIV) (Kalateh, Norouzi et al., 2008), [Hg(DPA)Cl2], (XV) (Yousefi et al., 2009), [Pt(DPA)Cl4].DMF, (XVI) (Abedi et al., 2011), [Ir(DPA)2Cl2](PF6), (XVII) (Yoshikawa et al., 2004), [Cu(DPA)2](BF4)2, (XVIII) (Clemente, 2005), [Mn(DPA)2(NCS)2].0.5H2O, (XIX) (Malecki et al., 2011) and [Au(DPA)Cl2]Cl, (XX) (Shi & Jiang, 2006). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the InIII atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating DPA ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg3···Cg3i [symmetry code: (i) -x, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring], with a centroid–centroid distance of 3.510 (3) Å, stabilize the structure.

For related structures, see: Abedi et al. (2011, 2012a,b); Ahmadi et al. (2008); Clemente (2005); Dong et al. (1987); Ilyuhin & Malyarik (1994); Kalateh, Ahmadi et al. (2008); Kalateh, Norouzi et al. (2008); Malecki et al. (2011); Malyarick et al. (1992); Shi & Jiang (2006); Shirvan & Haydari Dezfuli (2012); Yoshikawa et al. (2004); Yousefi et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
Trichlorido(dimethyl sulfoxide-κO)(di-2-pyridylamine-κ2N,N')indium(III) top
Crystal data top
[InCl3(C10H9N3)(C2H6OS)]F(000) = 1856
Mr = 470.51Dx = 1.784 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 14020 reflections
a = 29.283 (2) Åθ = 2.6–26.0°
b = 7.7642 (7) ŵ = 1.93 mm−1
c = 15.9459 (12) ÅT = 298 K
β = 104.891 (6)°Block, colorless
V = 3503.7 (5) Å30.20 × 0.18 × 0.15 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		3448 independent reflections
Radiation source: fine-focus sealed tube2503 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −29→36
Tmin = 0.702, Tmax = 0.796k = −9→9
14020 measured reflectionsl = −19→19
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0384P)2]
where P = (Fo2 + 2Fc2)/3
3448 reflections(Δ/σ)max = 0.007
192 parametersΔρmax = 0.72 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[InCl3(C10H9N3)(C2H6OS)]V = 3503.7 (5) Å3
Mr = 470.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 29.283 (2) ŵ = 1.93 mm−1
b = 7.7642 (7) ÅT = 298 K
c = 15.9459 (12) Å0.20 × 0.18 × 0.15 mm
β = 104.891 (6)°
Data collection top
Bruker APEXII CCD
diffractometer		3448 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2503 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.796Rint = 0.075
14020 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 0.99Δρmax = 0.72 e Å−3
3448 reflectionsΔρmin = −0.61 e Å−3
192 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
C10.1269 (2)0.2012 (6)0.2648 (3)0.0416 (13)
H10.12920.31980.27300.050*
C20.1331 (2)0.0973 (7)0.3361 (4)0.0444 (13)
H20.13970.14390.39160.053*
C30.12911 (19)−0.0815 (7)0.3234 (4)0.0422 (13)
H30.1334−0.15570.37050.051*
C40.11901 (18)−0.1440 (6)0.2417 (3)0.0363 (12)
H40.1167−0.26230.23250.044*
C50.11200 (16)−0.0330 (6)0.1712 (3)0.0301 (10)
C60.07132 (16)−0.0304 (5)0.0123 (3)0.0276 (10)
C70.04239 (18)−0.1417 (6)−0.0476 (3)0.0367 (12)
H70.0439−0.2600−0.03810.044*
C80.01195 (19)−0.0754 (7)−0.1202 (3)0.0433 (13)
H8−0.0075−0.1478−0.16050.052*
C90.01051 (18)0.1023 (7)−0.1329 (3)0.0415 (13)
H9−0.01050.1510−0.18100.050*
C100.04049 (17)0.2029 (6)−0.0735 (3)0.0355 (12)
H100.03930.3215−0.08190.043*
C110.2689 (2)0.1898 (9)0.1207 (5)0.0667 (19)
H11A0.26540.30900.13370.080*
H11B0.27350.17970.06350.080*
H11C0.29570.14250.16220.080*
C120.2306 (3)−0.1246 (8)0.0852 (6)0.090 (3)
H12A0.2358−0.10870.02860.108*
H12B0.2047−0.20240.08120.108*
H12C0.2586−0.17170.12360.108*
N10.11766 (14)0.1385 (4)0.1824 (3)0.0320 (9)
N20.09923 (15)−0.1004 (5)0.0877 (3)0.0341 (10)
H2B0.1104−0.20100.08220.041*
N30.07196 (13)0.1395 (4)−0.0027 (2)0.0289 (9)
O10.17759 (11)0.1461 (4)0.0516 (2)0.0371 (8)
In10.124091 (13)0.32946 (4)0.07746 (2)0.02991 (11)
Cl10.12945 (6)0.49624 (17)−0.04921 (10)0.0507 (4)
Cl20.18785 (6)0.48512 (18)0.17913 (10)0.0562 (4)
Cl30.05889 (5)0.49583 (15)0.10961 (9)0.0437 (3)
S10.21736 (5)0.07577 (18)0.12573 (10)0.0435 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.051 (3)0.035 (3)0.038 (3)0.005 (2)0.010 (3)−0.001 (2)
C20.054 (4)0.045 (3)0.033 (3)0.005 (3)0.010 (3)−0.006 (2)
C30.043 (3)0.047 (3)0.039 (3)0.009 (2)0.013 (3)0.013 (2)
C40.045 (3)0.021 (2)0.044 (3)0.005 (2)0.012 (2)0.004 (2)
C50.024 (2)0.030 (2)0.035 (3)0.0034 (19)0.007 (2)−0.001 (2)
C60.029 (3)0.023 (2)0.031 (3)−0.0002 (18)0.008 (2)0.0012 (18)
C70.042 (3)0.026 (2)0.042 (3)−0.006 (2)0.011 (2)−0.006 (2)
C80.040 (3)0.054 (3)0.034 (3)−0.011 (3)0.006 (3)−0.013 (2)
C90.030 (3)0.058 (3)0.034 (3)0.002 (2)0.003 (2)0.003 (2)
C100.037 (3)0.032 (3)0.038 (3)0.005 (2)0.011 (2)0.004 (2)
C110.040 (3)0.089 (5)0.066 (4)−0.002 (3)0.005 (3)0.027 (4)
C120.077 (5)0.051 (4)0.134 (8)0.032 (4)0.014 (5)0.002 (4)
N10.041 (2)0.0216 (19)0.032 (2)0.0007 (16)0.0073 (19)0.0021 (15)
N20.048 (3)0.0181 (16)0.033 (2)0.0054 (17)0.004 (2)−0.0015 (16)
N30.030 (2)0.0252 (19)0.029 (2)0.0008 (15)0.0041 (18)0.0008 (15)
O10.0319 (18)0.0387 (18)0.0377 (19)0.0067 (15)0.0035 (15)−0.0017 (15)
In10.03548 (19)0.01872 (14)0.03429 (18)−0.00068 (16)0.00671 (13)−0.00053 (15)
Cl10.0634 (9)0.0369 (6)0.0565 (9)0.0011 (6)0.0239 (8)0.0158 (6)
Cl20.0556 (9)0.0504 (8)0.0572 (9)−0.0182 (7)0.0048 (8)−0.0175 (7)
Cl30.0470 (8)0.0267 (6)0.0591 (8)0.0062 (5)0.0170 (7)−0.0020 (5)
S10.0354 (7)0.0489 (8)0.0454 (8)0.0085 (6)0.0092 (6)0.0139 (6)
Geometric parameters (Å, º) top
C1—N11.362 (7)C9—H90.9300
C1—C21.368 (8)C10—N31.353 (6)
C1—H10.9300C10—H100.9300
C2—C31.403 (7)C11—S11.768 (6)
C2—H20.9300C11—H11A0.9600
C3—C41.350 (7)C11—H11B0.9600
C3—H30.9300C11—H11C0.9600
C4—C51.389 (7)C12—S11.766 (7)
C4—H40.9300C12—H12A0.9600
C5—N11.347 (5)C12—H12B0.9600
C5—N21.390 (6)C12—H12C0.9600
C6—N31.342 (5)N1—In12.279 (4)
C6—N21.380 (6)N2—H2B0.8600
C6—C71.401 (6)N3—In12.267 (4)
C7—C81.367 (7)O1—S11.531 (3)
C7—H70.9300O1—In12.232 (3)
C8—C91.394 (8)In1—Cl12.4381 (14)
C8—H80.9300In1—Cl22.4535 (14)
C9—C101.361 (7)In1—Cl32.4658 (13)
N1—C1—C2122.8 (5)H11B—C11—H11C109.5
N1—C1—H1118.6S1—C12—H12A109.5
C2—C1—H1118.6S1—C12—H12B109.5
C1—C2—C3118.4 (5)H12A—C12—H12B109.5
C1—C2—H2120.8S1—C12—H12C109.5
C3—C2—H2120.8H12A—C12—H12C109.5
C4—C3—C2119.0 (5)H12B—C12—H12C109.5
C4—C3—H3120.5C5—N1—C1117.9 (4)
C2—C3—H3120.5C5—N1—In1125.2 (3)
C3—C4—C5120.5 (4)C1—N1—In1116.2 (3)
C3—C4—H4119.7C6—N2—C5129.8 (4)
C5—C4—H4119.7C6—N2—H2B115.1
N1—C5—C4121.2 (4)C5—N2—H2B115.1
N1—C5—N2119.5 (4)C6—N3—C10118.0 (4)
C4—C5—N2119.3 (4)C6—N3—In1125.2 (3)
N3—C6—N2120.7 (4)C10—N3—In1116.7 (3)
N3—C6—C7121.2 (4)S1—O1—In1121.04 (19)
N2—C6—C7118.0 (4)O1—In1—N383.32 (13)
C8—C7—C6119.6 (4)O1—In1—N185.12 (13)
C8—C7—H7120.2N3—In1—N179.63 (13)
C6—C7—H7120.2O1—In1—Cl189.31 (9)
C7—C8—C9119.0 (5)N3—In1—Cl193.18 (10)
C7—C8—H8120.5N1—In1—Cl1171.37 (10)
C9—C8—H8120.5O1—In1—Cl289.15 (9)
C10—C9—C8118.5 (5)N3—In1—Cl2168.87 (10)
C10—C9—H9120.8N1—In1—Cl291.60 (10)
C8—C9—H9120.8Cl1—In1—Cl294.92 (5)
N3—C10—C9123.4 (4)O1—In1—Cl3171.97 (9)
N3—C10—H10118.3N3—In1—Cl390.74 (10)
C9—C10—H10118.3N1—In1—Cl388.50 (10)
S1—C11—H11A109.5Cl1—In1—Cl396.44 (5)
S1—C11—H11B109.5Cl2—In1—Cl395.91 (5)
H11A—C11—H11B109.5O1—S1—C12103.1 (3)
S1—C11—H11C109.5O1—S1—C11106.0 (3)
H11A—C11—H11C109.5C12—S1—C1198.9 (4)
N1—C1—C2—C3−0.7 (9)C9—C10—N3—In1172.6 (4)
C1—C2—C3—C4−0.6 (8)S1—O1—In1—N3−128.7 (2)
C2—C3—C4—C5−0.9 (8)S1—O1—In1—N1−48.6 (2)
C3—C4—C5—N13.8 (8)S1—O1—In1—Cl1138.0 (2)
C3—C4—C5—N2−176.7 (5)S1—O1—In1—Cl243.1 (2)
N3—C6—C7—C8−4.3 (8)C6—N3—In1—O153.4 (4)
N2—C6—C7—C8175.6 (5)C10—N3—In1—O1−123.6 (3)
C6—C7—C8—C90.1 (8)C6—N3—In1—N1−32.9 (4)
C7—C8—C9—C101.7 (8)C10—N3—In1—N1150.2 (4)
C8—C9—C10—N30.5 (8)C6—N3—In1—Cl1142.3 (4)
C4—C5—N1—C1−5.0 (7)C10—N3—In1—Cl1−34.6 (3)
N2—C5—N1—C1175.5 (4)C6—N3—In1—Cl25.6 (8)
C4—C5—N1—In1165.3 (4)C10—N3—In1—Cl2−171.3 (4)
N2—C5—N1—In1−14.3 (6)C6—N3—In1—Cl3−121.2 (4)
C2—C1—N1—C53.5 (8)C10—N3—In1—Cl361.9 (3)
C2—C1—N1—In1−167.6 (4)C5—N1—In1—O1−48.7 (4)
N3—C6—N2—C535.4 (8)C1—N1—In1—O1121.6 (4)
C7—C6—N2—C5−144.5 (5)C5—N1—In1—N335.3 (4)
N1—C5—N2—C6−32.5 (7)C1—N1—In1—N3−154.3 (4)
C4—C5—N2—C6147.9 (5)C5—N1—In1—Cl2−137.7 (4)
N2—C6—N3—C10−173.5 (4)C1—N1—In1—Cl232.6 (4)
C7—C6—N3—C106.4 (7)C5—N1—In1—Cl3126.4 (4)
N2—C6—N3—In19.6 (6)C1—N1—In1—Cl3−63.2 (4)
C7—C6—N3—In1−170.5 (3)In1—O1—S1—C12153.0 (3)
C9—C10—N3—C6−4.5 (7)In1—O1—S1—C11−103.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11C···Cl2i0.962.743.499 (8)137
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[InCl3(C10H9N3)(C2H6OS)]
Mr470.51
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)29.283 (2), 7.7642 (7), 15.9459 (12)
β (°) 104.891 (6)
V (Å3)3503.7 (5)
Z8
Radiation typeMo Kα
µ (mm−1)1.93
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.702, 0.796
No. of measured, independent and
observed [I > 2σ(I)] reflections		14020, 3448, 2503
Rint0.075
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.080, 0.99
No. of reflections3448
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.72, −0.61

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11C···Cl2i0.962.743.499 (8)137
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.
 

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page m1256
https://doi.org/10.1107/S1600536812038147
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