Trichlorido(4,4'-dimethyl-2,2'-bipyridine-κN,N')(dimethyl sulfoxide-κO)indium(III).

In the mol-ecule of the title compound, [InCl(3)(C(12)H(12)N(2))(C(2)H(6)OS)], the In(III) atom is six-coordinated in a distorted octa-hedral configuration by two N atoms from the chelating 4,4'-dimethyl-2,2'-bipyridine ligand, one O atom from dimethyl sulfoxide and three Cl atoms. In the crystal structure, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For related literature, see: Ahmadi, Kalateh et al. (2008 ▶); Ahmadi, Khalighi et al. (2008 ▶); Amani et al. (2007 ▶); Ilyukhin & Malyarick (1994 ▶); Khavasi et al. (2007 ▶); Khalighi et al. (2008 ▶); Malyarick et al. (1992 ▶); Nan et al. (1987 ▶); Yousefi, Khalighi et al. (2008 ▶); Yousefi, Tadayon Pour et al. (2008 ▶).

Experimental

Crystal data

[InCl3(n class="CellLine">C12H12N2)(C2H6OS)]

M = 483.54

Monoclinic,

a = 8.2565 (17) Å

b = 23.456 (5) Å

c = 10.121 (2) Å

β = 105.95 (3)°

V = 1884.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.79 mm−1

T = 298 (2) K

0.49 × 0.46 × 0.44 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.404, T max = 0.455

13791 measured reflections

5046 independent reflections

4804 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.16

5046 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029553/hk2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029553/hk2532Isup2.hkl

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

[InCl3(C12H12N2)(C2H6OS)]	F(000) = 960
Mr = 483.54	Dx = 1.704 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2052 reflections
a = 8.2565 (17) Å	θ = 1.7–29.3°
b = 23.456 (5) Å	µ = 1.79 mm−1
c = 10.121 (2) Å	T = 298 K
β = 105.95 (3)°	Prism, colorless
V = 1884.7 (7) Å3	0.49 × 0.46 × 0.44 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5046 independent reflections
Radiation source: fine-focus sealed tube	4804 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 29.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.404, Tmax = 0.455	k = −28→32
13791 measured reflections	l = −13→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0263P)2 + 2.6542P] where P = (Fo2 + 2Fc2)/3
5046 reflections	(Δ/σ)max = 0.018
201 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.69 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
In1	0.67799 (2)	0.143868 (8)	0.722848 (19)	0.03114 (7)
Cl1	0.46060 (14)	0.15508 (4)	0.50881 (9)	0.0586 (2)
Cl2	0.89844 (14)	0.10102 (4)	0.63344 (12)	0.0620 (3)
Cl3	0.78999 (10)	0.24070 (3)	0.74202 (8)	0.04094 (16)
S1	0.41807 (11)	0.23105 (4)	0.82159 (9)	0.04457 (18)
O1	0.4998 (3)	0.17216 (10)	0.8405 (2)	0.0410 (5)
N1	0.5893 (3)	0.05448 (10)	0.7626 (2)	0.0345 (5)
N2	0.8245 (3)	0.11591 (10)	0.9400 (2)	0.0329 (5)
C1	0.4701 (4)	0.02601 (15)	0.6694 (3)	0.0443 (7)
H1	0.4125	0.0447	0.5892	0.053*
C2	0.4290 (4)	−0.03006 (14)	0.6877 (3)	0.0440 (7)
H2	0.3452	−0.0484	0.6207	0.053*
C3	0.5131 (4)	−0.05872 (13)	0.8059 (3)	0.0378 (6)
C4	0.4753 (5)	−0.12005 (14)	0.8289 (4)	0.0501 (8)
H4A	0.4398	−0.1232	0.9113	0.060*
H4B	0.5747	−0.1426	0.8378	0.060*
H4C	0.3872	−0.1335	0.7522	0.060*
C5	0.6370 (4)	−0.02882 (13)	0.9026 (3)	0.0369 (6)
H5	0.6968	−0.0468	0.9832	0.044*
C6	0.6714 (3)	0.02770 (12)	0.8790 (3)	0.0308 (5)
C7	0.8006 (3)	0.06232 (12)	0.9795 (3)	0.0311 (5)
C8	0.8859 (4)	0.04184 (13)	1.1078 (3)	0.0359 (6)
H8	0.8674	0.0047	1.1325	0.043*
C9	1.0000 (4)	0.07688 (13)	1.2006 (3)	0.0374 (6)
C10	1.0914 (5)	0.05639 (17)	1.3414 (4)	0.0530 (9)
H10A	1.0620	0.0799	1.4089	0.064*
H10B	1.2106	0.0585	1.3532	0.064*
H10C	1.0601	0.0176	1.3524	0.064*
C11	1.0221 (4)	0.13209 (14)	1.1568 (3)	0.0403 (6)
H11	1.0970	0.1569	1.2147	0.048*
C12	0.9325 (4)	0.14978 (13)	1.0270 (3)	0.0400 (6)
H12	0.9482	0.1867	0.9995	0.048*
C13	0.5259 (7)	0.2699 (2)	0.9695 (5)	0.0731 (13)
H13A	0.6407	0.2757	0.9686	0.088*
H13B	0.5234	0.2489	1.0504	0.088*
H13C	0.4720	0.3061	0.9699	0.088*
C14	0.2249 (5)	0.2199 (2)	0.8626 (5)	0.0722 (13)
H14A	0.2464	0.2014	0.9503	0.087*
H14B	0.1527	0.1963	0.7935	0.087*
H14C	0.1711	0.2559	0.8661	0.087*

	U11	U22	U33	U12	U13	U23
In1	0.03794 (11)	0.02645 (10)	0.03083 (10)	−0.00110 (7)	0.01249 (7)	0.00088 (7)
Cl1	0.0729 (6)	0.0538 (5)	0.0380 (4)	−0.0016 (4)	−0.0033 (4)	0.0062 (3)
Cl2	0.0772 (6)	0.0409 (4)	0.0877 (7)	0.0027 (4)	0.0561 (6)	−0.0066 (4)
Cl3	0.0448 (4)	0.0282 (3)	0.0536 (4)	−0.0030 (3)	0.0197 (3)	0.0006 (3)
S1	0.0475 (4)	0.0469 (4)	0.0438 (4)	0.0125 (3)	0.0200 (3)	0.0068 (3)
O1	0.0441 (11)	0.0412 (12)	0.0434 (11)	0.0053 (9)	0.0216 (9)	0.0042 (9)
N1	0.0379 (12)	0.0297 (12)	0.0350 (11)	−0.0049 (9)	0.0085 (9)	−0.0006 (9)
N2	0.0326 (11)	0.0296 (11)	0.0373 (12)	−0.0019 (9)	0.0111 (9)	0.0009 (9)
C1	0.0473 (17)	0.0394 (16)	0.0392 (15)	−0.0067 (14)	0.0002 (13)	0.0022 (12)
C2	0.0460 (17)	0.0384 (16)	0.0441 (16)	−0.0122 (13)	0.0067 (13)	−0.0062 (13)
C3	0.0455 (15)	0.0313 (14)	0.0406 (14)	−0.0055 (12)	0.0183 (12)	−0.0046 (11)
C4	0.068 (2)	0.0322 (16)	0.0527 (19)	−0.0109 (15)	0.0213 (17)	−0.0040 (14)
C5	0.0446 (15)	0.0312 (14)	0.0354 (13)	−0.0030 (12)	0.0116 (12)	0.0015 (11)
C6	0.0335 (12)	0.0290 (13)	0.0311 (12)	−0.0019 (10)	0.0109 (10)	−0.0028 (10)
C7	0.0329 (12)	0.0294 (13)	0.0321 (12)	0.0000 (10)	0.0109 (10)	−0.0018 (10)
C8	0.0405 (14)	0.0284 (13)	0.0382 (14)	−0.0002 (11)	0.0095 (11)	−0.0007 (11)
C9	0.0377 (14)	0.0364 (15)	0.0356 (14)	0.0029 (12)	0.0059 (11)	−0.0030 (11)
C10	0.061 (2)	0.051 (2)	0.0391 (16)	0.0022 (17)	−0.0007 (15)	0.0011 (14)
C11	0.0388 (15)	0.0365 (15)	0.0424 (15)	−0.0051 (12)	0.0058 (12)	−0.0067 (12)
C12	0.0416 (15)	0.0314 (14)	0.0478 (16)	−0.0073 (12)	0.0136 (13)	−0.0020 (12)
C13	0.091 (3)	0.064 (3)	0.079 (3)	−0.017 (2)	0.048 (3)	−0.028 (2)
C14	0.042 (2)	0.100 (4)	0.079 (3)	0.017 (2)	0.025 (2)	0.007 (3)

Cl1—In1	2.4180 (12)	C7—N2	1.350 (4)
Cl2—In1	2.4592 (10)	C7—C8	1.382 (4)
Cl3—In1	2.4398 (9)	C8—C9	1.400 (4)
O1—In1	2.233 (2)	C8—H8	0.9300
O1—S1	1.526 (2)	C9—C11	1.397 (4)
N1—In1	2.293 (2)	C9—C10	1.497 (4)
N2—In1	2.294 (2)	C10—H10A	0.9600
C1—N1	1.339 (4)	C10—H10B	0.9600
C1—C2	1.383 (5)	C10—H10C	0.9600
C1—H1	0.9300	C11—C12	1.382 (5)
C2—C3	1.382 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.331 (4)
C3—C5	1.395 (4)	C12—H12	0.9300
C3—C4	1.504 (4)	C13—S1	1.770 (5)
C4—H4A	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4C	0.9600	C13—H13C	0.9600
C5—C6	1.390 (4)	C14—S1	1.775 (4)
C5—H5	0.9300	C14—H14A	0.9600
C6—N1	1.343 (4)	C14—H14B	0.9600
C6—C7	1.495 (4)	C14—H14C	0.9600
Cl1—In1—Cl2	99.03 (4)	H4B—C4—H4C	109.5
Cl1—In1—Cl3	98.15 (3)	C6—C5—C3	120.3 (3)
Cl3—In1—Cl2	96.15 (3)	C6—C5—H5	119.9
O1—In1—Cl1	90.56 (7)	C3—C5—H5	119.9
O1—In1—Cl2	168.67 (6)	N1—C6—C5	121.3 (3)
O1—In1—Cl3	88.39 (6)	N1—C6—C7	115.9 (2)
O1—In1—N1	83.64 (9)	C5—C6—C7	122.8 (3)
O1—In1—N2	79.94 (9)	N2—C7—C8	121.6 (3)
N1—In1—Cl1	93.59 (7)	N2—C7—C6	116.1 (2)
N1—In1—Cl2	89.72 (7)	C8—C7—C6	122.3 (3)
N1—In1—Cl3	165.87 (6)	C7—C8—C9	120.1 (3)
N2—In1—Cl1	162.86 (7)	C7—C8—H8	119.9
N2—In1—Cl2	89.26 (7)	C9—C8—H8	119.9
N2—In1—Cl3	95.83 (7)	C11—C9—C8	117.0 (3)
N1—In1—N2	71.34 (9)	C11—C9—C10	121.6 (3)
O1—S1—C13	104.9 (2)	C8—C9—C10	121.4 (3)
O1—S1—C14	103.4 (2)	C9—C10—H10A	109.5
C13—S1—C14	98.8 (2)	C9—C10—H10B	109.5
H14B—C14—H14C	109.5	H10A—C10—H10B	109.5
S1—O1—In1	122.38 (12)	C9—C10—H10C	109.5
C1—N1—C6	118.7 (3)	H10A—C10—H10C	109.5
C1—N1—In1	122.7 (2)	H10B—C10—H10C	109.5
C6—N1—In1	118.26 (18)	C12—C11—C9	119.8 (3)
C12—N2—C7	119.1 (3)	C12—C11—H11	120.1
C12—N2—In1	123.0 (2)	C9—C11—H11	120.1
C7—N2—In1	117.94 (18)	N2—C12—C11	122.4 (3)
N1—C1—C2	122.7 (3)	N2—C12—H12	118.8
N1—C1—H1	118.7	C11—C12—H12	118.8
C2—C1—H1	118.7	S1—C13—H13A	109.5
C3—C2—C1	119.7 (3)	S1—C13—H13B	109.5
C3—C2—H2	120.2	H13A—C13—H13B	109.5
C1—C2—H2	120.2	S1—C13—H13C	109.5
C2—C3—C5	117.4 (3)	H13A—C13—H13C	109.5
C2—C3—C4	121.6 (3)	H13B—C13—H13C	109.5
C5—C3—C4	121.1 (3)	S1—C14—H14A	109.5
C3—C4—H4A	109.5	S1—C14—H14B	109.5
C3—C4—H4B	109.5	H14A—C14—H14B	109.5
H4A—C4—H4B	109.5	S1—C14—H14C	109.5
C3—C4—H4C	109.5	H14A—C14—H14C	109.5
H4A—C4—H4C	109.5
S1—O1—In1—N1	−154.51 (17)	N1—C1—C2—C3	−0.1 (5)
S1—O1—In1—N2	133.38 (17)	C1—C2—C3—C5	0.2 (5)
S1—O1—In1—Cl1	−60.97 (15)	C1—C2—C3—C4	−178.7 (3)
S1—O1—In1—Cl3	37.17 (15)	C2—C3—C5—C6	0.4 (5)
S1—O1—In1—Cl2	151.0 (2)	C4—C3—C5—C6	179.4 (3)
C1—N1—In1—O1	98.2 (3)	C3—C5—C6—N1	−1.2 (4)
C6—N1—In1—O1	−88.1 (2)	C3—C5—C6—C7	179.0 (3)
C1—N1—In1—N2	179.7 (3)	C5—C6—N1—C1	1.3 (4)
C6—N1—In1—N2	−6.6 (2)	C7—C6—N1—C1	−178.9 (3)
C1—N1—In1—Cl1	8.0 (3)	C5—C6—N1—In1	−172.7 (2)
C6—N1—In1—Cl1	−178.3 (2)	C7—C6—N1—In1	7.1 (3)
C1—N1—In1—Cl3	154.2 (2)	N1—C6—C7—N2	−2.2 (4)
C6—N1—In1—Cl3	−32.1 (4)	C5—C6—C7—N2	177.6 (3)
C1—N1—In1—Cl2	−91.0 (3)	N1—C6—C7—C8	175.1 (3)
C6—N1—In1—Cl2	82.7 (2)	C5—C6—C7—C8	−5.1 (4)
C12—N2—In1—O1	−88.9 (2)	C8—C7—N2—C12	−0.2 (4)
C7—N2—In1—O1	91.9 (2)	C6—C7—N2—C12	177.1 (3)
C12—N2—In1—N1	−175.5 (3)	C8—C7—N2—In1	179.0 (2)
C7—N2—In1—N1	5.30 (19)	C6—C7—N2—In1	−3.7 (3)
C12—N2—In1—Cl1	−146.1 (2)	N2—C7—C8—C9	0.2 (4)
C7—N2—In1—Cl1	34.7 (4)	C6—C7—C8—C9	−177.0 (3)
C12—N2—In1—Cl3	−1.6 (2)	C7—C8—C9—C11	−0.2 (4)
C7—N2—In1—Cl3	179.24 (19)	C7—C8—C9—C10	178.6 (3)
C12—N2—In1—Cl2	94.5 (2)	C8—C9—C11—C12	0.3 (5)
C7—N2—In1—Cl2	−84.65 (19)	C10—C9—C11—C12	−178.5 (3)
In1—O1—S1—C13	−105.2 (2)	C9—C11—C12—N2	−0.3 (5)
In1—O1—S1—C14	151.6 (2)	C11—C12—N2—C7	0.3 (5)
C2—C1—N1—C6	−0.6 (5)	C11—C12—N2—In1	−178.9 (2)
C2—C1—N1—In1	173.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.77	3.427 (4)	128.
C10—H10C···Cl2i	0.96	2.80	3.700 (4)	156.

Cl1—In1	2.4180 (12)
Cl2—In1	2.4592 (10)
Cl3—In1	2.4398 (9)
O1—In1	2.233 (2)
N1—In1	2.293 (2)
N2—In1	2.294 (2)

Cl1—In1—Cl2	99.03 (4)
Cl1—In1—Cl3	98.15 (3)
Cl3—In1—Cl2	96.15 (3)
O1—In1—Cl1	90.56 (7)
O1—In1—Cl2	168.67 (6)
O1—In1—Cl3	88.39 (6)
O1—In1—N1	83.64 (9)
O1—In1—N2	79.94 (9)
N1—In1—Cl1	93.59 (7)
N1—In1—Cl2	89.72 (7)
N1—In1—Cl3	165.87 (6)
N2—In1—Cl1	162.86 (7)
N2—In1—Cl2	89.26 (7)
N2—In1—Cl3	95.83 (7)
N1—In1—N2	71.34 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.93	2.77	3.427 (4)	128
C10—H10C⋯Cl2i	0.96	2.80	3.700 (4)	156

Symmetry code: (i) .