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

In the title compound, [In(C(11)H(10)N(2))Cl(3)(C(2)H(6)OS)], the In(III) cation is six-coordinated in a distorted octa-hedral configuration by two N atoms from the chelating 6-methyl-2,2'-bipyridine ligand, one O atom from a dimethyl-sulfoxide group and three Cl(-) anions. Weak inter-molecular C-H⋯O and C-H⋯Cl hydrogen bonds and intra-molecular 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 = 469.52

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.04

3496 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.54 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041049/xu5625sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041049/xu5625Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[In(C11H10N2)Cl3(C2H6OS)]	F(000) = 928
Mr = 469.52	Dx = 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

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

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(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
3496 reflections	(Δ/σ)max = 0.013
192 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .