Trichlorido(6-methyl-2,2′-bipyridine-κ2N,N′)(dimethyl­sulfoxide-κO)indium(III)

Shirvan, S.A.; Haydari Dezfuli, S.; Golabi, E.; Gholamzadeh, M.A.

doi:10.1107/S1600536812041049

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1327-m1328

doi:10.1107/S1600536812041049

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Trichlorido(6-methyl-2,2′-bipyridine-κ²N,N′)(dimethylsulfoxide-κO)indium(III)

Sadif A. Shirvan,^a ^* Sara Haydari Dezfuli,^a Elyas Golabi ^b and Mohammad Amin Gholamzadeh ^b

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

(Received 28 September 2012; accepted 30 September 2012; online 6 October 2012)

In the title compound, [In(C₁₁H₁₀N₂)Cl₃(C₂H₆OS)], the In^III cation is six-coordinated in a distorted octahedral configuration by two N atoms from the chelating 6-methyl-2,2′-bipyridine ligand, one O atom from a dimethylsulfoxide group and three Cl⁻ anions. Weak intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds and intramolecular C—H⋯Cl hydrogen bonds are present in the structure.

Related literature

For related structures, see: Abedi et al. (2012a ,b ); Ahmadi et al. (2008a ,b ,c , 2009 ); Amani et al. (2009 ); Ilyukhin et al. (1994 ); Kalateh et al. (2008 , 2010 ); Malyarick et al. (1992 ); Nan et al. (1987 ); Newkome et al. (1982 ); Onggo et al. (1990 , 2005 ); Shirvan & Haydari Dezfuli (2012a ,b ); Shirvan et al. (2012 ).

Experimental

Crystal data

[In(C₁₁H₁₀N₂)Cl₃(C₂H₆OS)]
M_r = 469.52
Monoclinic, P 2₁ /c
a = 13.0169 (6) Å
b = 8.5548 (3) Å
c = 15.9964 (8) Å
β = 93.393 (4)°
V = 1778.19 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.90 mm⁻¹
T = 298 K
0.40 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.581, T_max = 0.701
14275 measured reflections
3496 independent reflections
2831 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.076
S = 1.04
3496 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected bond lengths (Å)

In1—Cl1	2.4330 (10)
In1—Cl2	2.4468 (11)
In1—Cl3	2.4309 (9)
In1—O1	2.227 (2)
In1—N1	2.270 (3)
In1—N2	2.398 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl2	0.93	2.75	3.348 (5)	123
C11—H11B⋯Cl3	0.96	2.56	3.358 (6)	140
C13—H13A⋯O1ⁱ	0.96	2.47	3.419 (6)	169
C13—H13C⋯Cl2ⁱⁱ	0.96	2.82	3.612 (5)	141
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041049/xu5625sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041049/xu5625Isup2.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, 2012a) and [In{NH(py)₂)Cl₃(DMSO)], (III), (Shirvan & Haydari Dezfuli, 2012b) [where 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine and NH(py)₂ is di-2-pyridylamine]. There are several In^III complexes, with formula, [In(N—N)Cl₃(L)], (L = DMSO, H₂O, MeOH and EtOH), such as [In(bipy)Cl₃(H₂O)], (IV), [In(bipy)Cl₃(EtOH)], (V) and [In(bipy)Cl₃(H₂O)].H₂O, (VI), (Malyarick et al., 1992), [In(phen)Cl₃(DMSO)], (VII), (Nan et al., 1987), [In(phen)Cl₃(H₂O)], (VIII) and [In(phen)Cl₃(EtOH)].EtOH, (IX), (Ilyukhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl₃(DMSO)], (X), (Ahmadi et al., 2008a), [In(5,5'-dmbipy)Cl₃(MeOH)], (XI), (Kalateh et al., 2008), [In(4,4'-dtbipy)Cl₃(MeOH)].0.5MeOH, (XII), (Abedi et al., 2012a), [In(4 b t)Cl₃(MeOH)], (XIII) and [In(4 b t)Cl₃(DMSO)], (XIV), (Abedi et al., 2012b) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, DMSO is dimethyl sulfoxide, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dtbipy is 4,4'-di-τert-butyl-2,2'-bipyridine and 4 b t is 4,4'-bithiazole] have been synthesized and characterized by single-crystal X-ray diffraction methods. 6-Methyl-2,2'-bipyridine (6-mbipy) is a good ligand and a few complexes with 6-mbipy have been prepared, such as that of [Hg(6-mbipy)Cl₂], (XV), (Ahmadi et al., 2008b), [Pt(6-mbipy)Cl₄], (XVI), (Amani et al., 2009), [Pb₄(NO₃)₈(6-mbipy)₄], (XVII), (Ahmadi et al., 2009), [Zn(6-mbipy)Br₂], (XVIII), (Kalateh et al., 2010), [Zn(6-mbipy)Cl₂], (IXX), (Ahmadi et al., 2008c), [Pd(6-mbipy)Cl₂], (XX), (Newkome et al., 1982), [Ru(6-mbipy)₃][BF₄]₂, (XXI), (Onggo et al., 2005), [Fe(6-mbipy)₃][ClO₄]₂.6-mbipy, (XXII), (Onggo et al., 1990), and [Cd(6-mbipy)Br₂(DMSO)], (XXIII), (Shirvan et al., 2012). We report herein the synthesis and crystal structure of the title compound (I).

In the title compound, (Fig. 1), the In^III atom is six-coordinated in a distorted octahedral configuration by two N atoms from the chelating 6-methyl-2,2'-bipyridine ligand, one O atom from a dimethyl sulfoxide and three Cl atoms. The In—Cl, In—N and In—O bond lengths and angles are collected in Table 1.

In the crystal structure, intermolecular C—H···O and C—H···Cl hydrogen bonds and π-π contact (Table 2 & Fig. 2) between the pyridine rings, Cg3—Cg3ⁱ [symmetry cods: (i) –X,2-Y,-Z, where Cg3 is centroid of the ring (N2/C6—C10)] may stabilize the structure, with centroid-centroid distance 3.774 (2) Å.

Related literature top

For related structures, see: Abedi et al. (2012a,b); Ahmadi et al. (2008a,b,c, 2009); Amani et al. (2009); Ilyukhin et al. (1994); Kalateh et al. (2008, 2010); Malyarick et al. (1992); Nan et al. (1987); Newkome et al. (1982); Onggo et al. (1990, 2005); Shirvan & Haydari Dezfuli (2012a,b); Shirvan et al. (2012).

Experimental top

For the preparation of the title compound, (I), a solution of 6-methyl-2,2'-bipyridine (0.28 g, 0.26 ml, 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 experiment were obtained by methanol diffusion to a colorless solution in DMSO. Suitable crystals were isolated after one week (yield; 0.56 g, 72.3%).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Unit-cell packing diagram for title molecule. Hydrogen bonds are shown as dashed lines.

Trichlorido(6-methyl-2,2'-bipyridine-κ²N,N')(dimethyl sulfoxide-κO)indium (III) top

Crystal data top

[In(C₁₁H₁₀N₂)Cl₃(C₂H₆OS)]	F(000) = 928
M_r = 469.52	D_x = 1.754 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14275 reflections
a = 13.0169 (6) Å	θ = 1.6–26.0°
b = 8.5548 (3) Å	µ = 1.90 mm⁻¹
c = 15.9964 (8) Å	T = 298 K
β = 93.393 (4)°	Prism, colorless
V = 1778.19 (14) Å³	0.40 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area detector diffractometer	3496 independent reflections
Radiation source: fine-focus sealed tube	2831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→15
T_min = 0.581, T_max = 0.701	k = −10→10
14275 measured reflections	l = −17→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.042P)²] where P = (F_o² + 2F_c²)/3
3496 reflections	(Δ/σ)_max = 0.013
192 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[In(C₁₁H₁₀N₂)Cl₃(C₂H₆OS)]	V = 1778.19 (14) Å³
M_r = 469.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0169 (6) Å	µ = 1.90 mm⁻¹
b = 8.5548 (3) Å	T = 298 K
c = 15.9964 (8) Å	0.40 × 0.25 × 0.20 mm
β = 93.393 (4)°

Data collection top

Bruker APEXII CCD area detector diffractometer	3496 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2831 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.701	R_int = 0.053
14275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	Δρ_max = 0.65 e Å⁻³
3496 reflections	Δρ_min = −0.54 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

	x	y	z	U_iso*/U_eq
N1	0.2514 (2)	0.9449 (3)	0.13539 (18)	0.0467 (7)
Cl1	0.12219 (10)	0.60548 (12)	0.13692 (9)	0.0801 (4)
C11	0.0925 (4)	0.6719 (6)	−0.1127 (4)	0.0878 (16)
H11A	0.0557	0.6185	−0.0709	0.105*
H11B	0.1589	0.6247	−0.1165	0.105*
H11C	0.0545	0.6644	−0.1658	0.105*
Cl2	0.40731 (9)	0.63682 (14)	0.17190 (7)	0.0715 (3)
N2	0.1563 (2)	0.8750 (3)	−0.01655 (19)	0.0455 (7)
C5	0.2065 (3)	1.0631 (4)	0.0914 (2)	0.0453 (8)
C2	0.2834 (4)	1.1141 (5)	0.2520 (3)	0.0704 (12)
H2	0.3095	1.1284	0.3069	0.084*
C3	0.2403 (4)	1.2359 (5)	0.2066 (3)	0.0676 (12)
H3	0.2373	1.3349	0.2304	0.081*
In1	0.269337 (19)	0.71247 (3)	0.069351 (15)	0.04247 (9)
C6	0.1608 (3)	1.0271 (4)	0.0064 (2)	0.0458 (8)
Cl3	0.30194 (9)	0.49559 (11)	−0.02363 (7)	0.0630 (3)
S1	0.38648 (7)	0.84709 (11)	−0.09440 (5)	0.0444 (2)
C9	0.0639 (3)	0.9526 (7)	−0.1425 (3)	0.0697 (12)
H9	0.0300	0.9247	−0.1932	0.084*
C12	0.5099 (4)	0.7693 (6)	−0.1071 (3)	0.0766 (13)
H12C	0.5248	0.7738	−0.1651	0.092*
H12B	0.5121	0.6626	−0.0885	0.092*
H12A	0.5602	0.8292	−0.0745	0.092*
C10	0.1050 (3)	0.8364 (5)	−0.0894 (3)	0.0572 (10)
C13	0.4079 (4)	1.0435 (5)	−0.1239 (3)	0.0660 (11)
H13A	0.4648	1.0855	−0.0902	0.079*
H13B	0.3473	1.1042	−0.1157	0.079*
H13C	0.4232	1.0472	−0.1819	0.079*
C8	0.0727 (4)	1.1049 (7)	−0.1215 (3)	0.0752 (13)
H8	0.0467	1.1820	−0.1579	0.090*
C1	0.2870 (4)	0.9711 (5)	0.2141 (2)	0.0635 (11)
H1	0.3156	0.8878	0.2448	0.076*
C7	0.1207 (3)	1.1444 (5)	−0.0456 (3)	0.0668 (11)
H7	0.1262	1.2486	−0.0293	0.080*
O1	0.37807 (18)	0.8589 (3)	0.00075 (14)	0.0470 (6)
C4	0.2017 (3)	1.2113 (4)	0.1264 (3)	0.0581 (10)
H4	0.1722	1.2935	0.0954	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0648 (19)	0.0362 (15)	0.0397 (16)	−0.0001 (13)	0.0090 (13)	0.0021 (13)
Cl1	0.0865 (8)	0.0494 (6)	0.1099 (9)	−0.0006 (5)	0.0514 (7)	0.0107 (6)
C11	0.080 (3)	0.086 (4)	0.093 (4)	−0.007 (3)	−0.024 (3)	−0.025 (3)
Cl2	0.0945 (8)	0.0633 (6)	0.0549 (6)	0.0203 (6)	−0.0109 (5)	0.0082 (5)
N2	0.0420 (15)	0.0475 (17)	0.0473 (17)	−0.0019 (13)	0.0036 (13)	0.0010 (13)
C5	0.0477 (19)	0.0385 (18)	0.051 (2)	−0.0012 (15)	0.0133 (16)	0.0036 (15)
C2	0.105 (3)	0.059 (3)	0.048 (2)	−0.010 (2)	0.010 (2)	−0.010 (2)
C3	0.088 (3)	0.044 (2)	0.072 (3)	−0.004 (2)	0.018 (2)	−0.013 (2)
In1	0.05532 (16)	0.03124 (13)	0.04150 (14)	0.00100 (11)	0.00834 (10)	0.00223 (10)
C6	0.0443 (18)	0.0391 (18)	0.055 (2)	0.0020 (14)	0.0118 (16)	0.0051 (16)
Cl3	0.0866 (7)	0.0446 (5)	0.0588 (6)	0.0033 (5)	0.0124 (5)	−0.0110 (4)
S1	0.0469 (5)	0.0475 (5)	0.0386 (4)	−0.0044 (4)	0.0013 (4)	0.0013 (4)
C9	0.053 (2)	0.102 (4)	0.053 (2)	0.010 (2)	−0.0027 (19)	0.002 (3)
C12	0.072 (3)	0.092 (3)	0.067 (3)	0.027 (3)	0.017 (2)	0.000 (3)
C10	0.046 (2)	0.069 (3)	0.056 (2)	−0.0017 (18)	0.0019 (18)	−0.007 (2)
C13	0.094 (3)	0.056 (2)	0.048 (2)	−0.006 (2)	0.004 (2)	0.0128 (19)
C8	0.079 (3)	0.088 (4)	0.058 (3)	0.024 (3)	0.000 (2)	0.017 (2)
C1	0.099 (3)	0.050 (2)	0.042 (2)	−0.002 (2)	0.006 (2)	0.0023 (17)
C7	0.079 (3)	0.057 (2)	0.065 (3)	0.016 (2)	0.009 (2)	0.014 (2)
O1	0.0514 (14)	0.0532 (14)	0.0367 (13)	−0.0085 (11)	0.0046 (10)	0.0020 (11)
C4	0.067 (2)	0.0359 (18)	0.073 (3)	0.0062 (18)	0.010 (2)	−0.0004 (19)

Geometric parameters (Å, º) top

In1—Cl1	2.4330 (10)	C3—H3	0.9300
In1—Cl2	2.4468 (11)	C6—C7	1.385 (5)
In1—Cl3	2.4309 (9)	S1—O1	1.536 (2)
In1—O1	2.227 (2)	S1—C12	1.762 (4)
In1—N1	2.270 (3)	S1—C13	1.772 (4)
In1—N2	2.398 (3)	C9—C8	1.348 (7)
N1—C1	1.335 (5)	C9—C10	1.394 (6)
N1—C5	1.346 (4)	C9—H9	0.9300
C11—C10	1.462 (6)	C12—H12C	0.9600
C11—H11A	0.9600	C12—H12B	0.9600
C11—H11B	0.9600	C12—H12A	0.9600
C11—H11C	0.9600	C13—H13A	0.9600
N2—C10	1.349 (5)	C13—H13B	0.9600
N2—C6	1.353 (4)	C13—H13C	0.9600
C5—C4	1.390 (5)	C8—C7	1.376 (7)
C5—C6	1.483 (5)	C8—H8	0.9300
C2—C1	1.368 (6)	C1—H1	0.9300
C2—C3	1.371 (7)	C7—H7	0.9300
C2—H2	0.9300	C4—H4	0.9300
C3—C4	1.367 (7)

C1—N1—C5	118.9 (3)	N2—C6—C5	117.2 (3)
C1—N1—In1	123.2 (3)	C7—C6—C5	121.1 (3)
C5—N1—In1	117.9 (2)	O1—S1—C12	104.9 (2)
C10—C11—H11A	109.5	O1—S1—C13	102.90 (18)
C10—C11—H11B	109.5	C12—S1—C13	99.7 (2)
H11A—C11—H11B	109.5	C8—C9—C10	120.9 (4)
C10—C11—H11C	109.5	C8—C9—H9	119.6
H11A—C11—H11C	109.5	C10—C9—H9	119.6
H11B—C11—H11C	109.5	S1—C12—H12C	109.5
C10—N2—C6	118.8 (3)	S1—C12—H12B	109.5
C10—N2—In1	127.5 (3)	H12C—C12—H12B	109.5
C6—N2—In1	112.8 (2)	S1—C12—H12A	109.5
N1—C5—C4	120.2 (4)	H12C—C12—H12A	109.5
N1—C5—C6	117.5 (3)	H12B—C12—H12A	109.5
C4—C5—C6	122.2 (3)	N2—C10—C9	120.3 (4)
C1—C2—C3	117.9 (4)	N2—C10—C11	119.8 (4)
C1—C2—H2	121.0	C9—C10—C11	119.9 (4)
C3—C2—H2	121.0	S1—C13—H13A	109.5
C4—C3—C2	119.8 (4)	S1—C13—H13B	109.5
C4—C3—H3	120.1	H13A—C13—H13B	109.5
C2—C3—H3	120.1	S1—C13—H13C	109.5
O1—In1—N1	79.77 (10)	H13A—C13—H13C	109.5
O1—In1—N2	77.17 (9)	H13B—C13—H13C	109.5
N1—In1—N2	71.48 (10)	C9—C8—C7	119.0 (4)
O1—In1—Cl3	89.36 (7)	C9—C8—H8	120.5
N1—In1—Cl3	168.44 (8)	C7—C8—H8	120.5
N2—In1—Cl3	102.44 (8)	N1—C1—C2	123.3 (4)
O1—In1—Cl1	166.02 (7)	N1—C1—H1	118.3
N1—In1—Cl1	91.00 (8)	C2—C1—H1	118.3
N2—In1—Cl1	90.00 (7)	C8—C7—C6	119.2 (4)
Cl3—In1—Cl1	98.93 (4)	C8—C7—H7	120.4
O1—In1—Cl2	90.94 (7)	C6—C7—H7	120.4
N1—In1—Cl2	90.64 (8)	S1—O1—In1	122.40 (14)
N2—In1—Cl2	159.89 (8)	C3—C4—C5	119.7 (4)
Cl3—In1—Cl2	93.47 (4)	C3—C4—H4	120.1
Cl1—In1—Cl2	99.71 (5)	C5—C4—H4	120.1
N2—C6—C7	121.7 (4)

C1—N1—C5—C4	2.8 (5)	In1—N2—C6—C5	−17.8 (4)
In1—N1—C5—C4	−174.4 (3)	N1—C5—C6—N2	7.9 (5)
C1—N1—C5—C6	−175.5 (3)	C4—C5—C6—N2	−170.3 (3)
In1—N1—C5—C6	7.3 (4)	N1—C5—C6—C7	−174.6 (3)
C1—C2—C3—C4	0.6 (7)	C4—C5—C6—C7	7.1 (5)
C1—N1—In1—O1	−109.3 (3)	C6—N2—C10—C9	4.4 (5)
C5—N1—In1—O1	67.8 (2)	In1—N2—C10—C9	−163.4 (3)
C1—N1—In1—N2	170.9 (3)	C6—N2—C10—C11	−175.5 (4)
C5—N1—In1—N2	−12.0 (2)	In1—N2—C10—C11	16.7 (5)
C1—N1—In1—Cl3	−129.4 (4)	C8—C9—C10—N2	−1.3 (6)
C5—N1—In1—Cl3	47.8 (6)	C8—C9—C10—C11	178.6 (5)
C1—N1—In1—Cl1	81.2 (3)	C10—C9—C8—C7	−1.7 (7)
C5—N1—In1—Cl1	−101.6 (2)	C5—N1—C1—C2	−2.3 (6)
C1—N1—In1—Cl2	−18.5 (3)	In1—N1—C1—C2	174.8 (3)
C5—N1—In1—Cl2	158.7 (2)	C3—C2—C1—N1	0.6 (7)
C10—N2—In1—O1	100.7 (3)	C9—C8—C7—C6	1.5 (7)
C6—N2—In1—O1	−67.7 (2)	N2—C6—C7—C8	1.7 (6)
C10—N2—In1—N1	−176.0 (3)	C5—C6—C7—C8	−175.6 (4)
C6—N2—In1—N1	15.6 (2)	C12—S1—O1—In1	−112.8 (2)
C10—N2—In1—Cl3	14.2 (3)	C13—S1—O1—In1	143.3 (2)
C6—N2—In1—Cl3	−154.2 (2)	N1—In1—O1—S1	−139.25 (18)
C10—N2—In1—Cl1	−84.9 (3)	N2—In1—O1—S1	−66.10 (17)
C6—N2—In1—Cl1	106.7 (2)	Cl3—In1—O1—S1	36.81 (16)
C10—N2—In1—Cl2	155.7 (2)	Cl1—In1—O1—S1	−89.9 (3)
C6—N2—In1—Cl2	−12.7 (4)	Cl2—In1—O1—S1	130.27 (16)
C10—N2—C6—C7	−4.7 (5)	C2—C3—C4—C5	−0.1 (7)
In1—N2—C6—C7	164.9 (3)	N1—C5—C4—C3	−1.7 (6)
C10—N2—C6—C5	172.7 (3)	C6—C5—C4—C3	176.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93	2.75	3.348 (5)	123
C11—H11B···Cl3	0.96	2.56	3.358 (6)	140
C13—H13A···O1ⁱ	0.96	2.47	3.419 (6)	169
C13—H13C···Cl2ⁱⁱ	0.96	2.82	3.612 (5)	141

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[In(C₁₁H₁₀N₂)Cl₃(C₂H₆OS)]
M_r	469.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.0169 (6), 8.5548 (3), 15.9964 (8)
β (°)	93.393 (4)
V (Å³)	1778.19 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.581, 0.701
No. of measured, independent and observed [I > 2σ(I)] reflections	14275, 3496, 2831
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.04
No. of reflections	3496
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.54

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

In1—Cl1	2.4330 (10)	In1—O1	2.227 (2)
In1—Cl2	2.4468 (11)	In1—N1	2.270 (3)
In1—Cl3	2.4309 (9)	In1—N2	2.398 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93	2.75	3.348 (5)	123
C11—H11B···Cl3	0.96	2.56	3.358 (6)	140
C13—H13A···O1ⁱ	0.96	2.47	3.419 (6)	169
C13—H13C···Cl2ⁱⁱ	0.96	2.82	3.612 (5)	141

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x, −y+3/2, z−1/2.

Acknowledgements

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

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