Trichlorido(dimethyl sulfoxide-κO)(di-2-pyridyl-amine-κ(2)N,N')indium(III).

In the title compound, [InCl(3)(C(10)H(9)N(3))(C(2)H(6)OS)], the In(III) atom is six-coordinated in a distorted octa-hedral geometry by two N atoms from a chelating di-2-pyridyl-amine ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. Inter-molecular 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 ▶, 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

Crystal data

[InCl3(C10H9N3)(C2H6OS)]

M = 470.51

Monoclinic,

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 ▶) T min = 0.702, T max = 0.796

14020 measured reflections

3448 independent reflections

2503 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 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

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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038147/hy2584sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038147/hy2584Isup2.hkl

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

[InCl3(C10H9N3)(C2H6OS)]	F(000) = 1856
Mr = 470.51	Dx = 1.784 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14020 reflections
a = 29.283 (2) Å	θ = 2.6–26.0°
b = 7.7642 (7) Å	µ = 1.93 mm−1
c = 15.9459 (12) Å	T = 298 K
β = 104.891 (6)°	Block, colorless
V = 3503.7 (5) Å3	0.20 × 0.18 × 0.15 mm
Z = 8

Bruker APEXII CCD diffractometer	3448 independent reflections
Radiation source: fine-focus sealed tube	2503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −29→36
Tmin = 0.702, Tmax = 0.796	k = −9→9
14020 measured reflections	l = −19→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-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 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.61 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
C1	0.1269 (2)	0.2012 (6)	0.2648 (3)	0.0416 (13)
H1	0.1292	0.3198	0.2730	0.050*
C2	0.1331 (2)	0.0973 (7)	0.3361 (4)	0.0444 (13)
H2	0.1397	0.1439	0.3916	0.053*
C3	0.12911 (19)	−0.0815 (7)	0.3234 (4)	0.0422 (13)
H3	0.1334	−0.1557	0.3705	0.051*
C4	0.11901 (18)	−0.1440 (6)	0.2417 (3)	0.0363 (12)
H4	0.1167	−0.2623	0.2325	0.044*
C5	0.11200 (16)	−0.0330 (6)	0.1712 (3)	0.0301 (10)
C6	0.07132 (16)	−0.0304 (5)	0.0123 (3)	0.0276 (10)
C7	0.04239 (18)	−0.1417 (6)	−0.0476 (3)	0.0367 (12)
H7	0.0439	−0.2600	−0.0381	0.044*
C8	0.01195 (19)	−0.0754 (7)	−0.1202 (3)	0.0433 (13)
H8	−0.0075	−0.1478	−0.1605	0.052*
C9	0.01051 (18)	0.1023 (7)	−0.1329 (3)	0.0415 (13)
H9	−0.0105	0.1510	−0.1810	0.050*
C10	0.04049 (17)	0.2029 (6)	−0.0735 (3)	0.0355 (12)
H10	0.0393	0.3215	−0.0819	0.043*
C11	0.2689 (2)	0.1898 (9)	0.1207 (5)	0.0667 (19)
H11A	0.2654	0.3090	0.1337	0.080*
H11B	0.2735	0.1797	0.0635	0.080*
H11C	0.2957	0.1425	0.1622	0.080*
C12	0.2306 (3)	−0.1246 (8)	0.0852 (6)	0.090 (3)
H12A	0.2358	−0.1087	0.0286	0.108*
H12B	0.2047	−0.2024	0.0812	0.108*
H12C	0.2586	−0.1717	0.1236	0.108*
N1	0.11766 (14)	0.1385 (4)	0.1824 (3)	0.0320 (9)
N2	0.09923 (15)	−0.1004 (5)	0.0877 (3)	0.0341 (10)
H2B	0.1104	−0.2010	0.0822	0.041*
N3	0.07196 (13)	0.1395 (4)	−0.0027 (2)	0.0289 (9)
O1	0.17759 (11)	0.1461 (4)	0.0516 (2)	0.0371 (8)
In1	0.124091 (13)	0.32946 (4)	0.07746 (2)	0.02991 (11)
Cl1	0.12945 (6)	0.49624 (17)	−0.04921 (10)	0.0507 (4)
Cl2	0.18785 (6)	0.48512 (18)	0.17913 (10)	0.0562 (4)
Cl3	0.05889 (5)	0.49583 (15)	0.10961 (9)	0.0437 (3)
S1	0.21736 (5)	0.07577 (18)	0.12573 (10)	0.0435 (3)

	U11	U22	U33	U12	U13	U23
C1	0.051 (3)	0.035 (3)	0.038 (3)	0.005 (2)	0.010 (3)	−0.001 (2)
C2	0.054 (4)	0.045 (3)	0.033 (3)	0.005 (3)	0.010 (3)	−0.006 (2)
C3	0.043 (3)	0.047 (3)	0.039 (3)	0.009 (2)	0.013 (3)	0.013 (2)
C4	0.045 (3)	0.021 (2)	0.044 (3)	0.005 (2)	0.012 (2)	0.004 (2)
C5	0.024 (2)	0.030 (2)	0.035 (3)	0.0034 (19)	0.007 (2)	−0.001 (2)
C6	0.029 (3)	0.023 (2)	0.031 (3)	−0.0002 (18)	0.008 (2)	0.0012 (18)
C7	0.042 (3)	0.026 (2)	0.042 (3)	−0.006 (2)	0.011 (2)	−0.006 (2)
C8	0.040 (3)	0.054 (3)	0.034 (3)	−0.011 (3)	0.006 (3)	−0.013 (2)
C9	0.030 (3)	0.058 (3)	0.034 (3)	0.002 (2)	0.003 (2)	0.003 (2)
C10	0.037 (3)	0.032 (3)	0.038 (3)	0.005 (2)	0.011 (2)	0.004 (2)
C11	0.040 (3)	0.089 (5)	0.066 (4)	−0.002 (3)	0.005 (3)	0.027 (4)
C12	0.077 (5)	0.051 (4)	0.134 (8)	0.032 (4)	0.014 (5)	0.002 (4)
N1	0.041 (2)	0.0216 (19)	0.032 (2)	0.0007 (16)	0.0073 (19)	0.0021 (15)
N2	0.048 (3)	0.0181 (16)	0.033 (2)	0.0054 (17)	0.004 (2)	−0.0015 (16)
N3	0.030 (2)	0.0252 (19)	0.029 (2)	0.0008 (15)	0.0041 (18)	0.0008 (15)
O1	0.0319 (18)	0.0387 (18)	0.0377 (19)	0.0067 (15)	0.0035 (15)	−0.0017 (15)
In1	0.03548 (19)	0.01872 (14)	0.03429 (18)	−0.00068 (16)	0.00671 (13)	−0.00053 (15)
Cl1	0.0634 (9)	0.0369 (6)	0.0565 (9)	0.0011 (6)	0.0239 (8)	0.0158 (6)
Cl2	0.0556 (9)	0.0504 (8)	0.0572 (9)	−0.0182 (7)	0.0048 (8)	−0.0175 (7)
Cl3	0.0470 (8)	0.0267 (6)	0.0591 (8)	0.0062 (5)	0.0170 (7)	−0.0020 (5)
S1	0.0354 (7)	0.0489 (8)	0.0454 (8)	0.0085 (6)	0.0092 (6)	0.0139 (6)

C1—N1	1.362 (7)	C9—H9	0.9300
C1—C2	1.368 (8)	C10—N3	1.353 (6)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.403 (7)	C11—S1	1.768 (6)
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.350 (7)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.389 (7)	C12—S1	1.766 (7)
C4—H4	0.9300	C12—H12A	0.9600
C5—N1	1.347 (5)	C12—H12B	0.9600
C5—N2	1.390 (6)	C12—H12C	0.9600
C6—N3	1.342 (5)	N1—In1	2.279 (4)
C6—N2	1.380 (6)	N2—H2B	0.8600
C6—C7	1.401 (6)	N3—In1	2.267 (4)
C7—C8	1.367 (7)	O1—S1	1.531 (3)
C7—H7	0.9300	O1—In1	2.232 (3)
C8—C9	1.394 (8)	In1—Cl1	2.4381 (14)
C8—H8	0.9300	In1—Cl2	2.4535 (14)
C9—C10	1.361 (7)	In1—Cl3	2.4658 (13)
N1—C1—C2	122.8 (5)	H11B—C11—H11C	109.5
N1—C1—H1	118.6	S1—C12—H12A	109.5
C2—C1—H1	118.6	S1—C12—H12B	109.5
C1—C2—C3	118.4 (5)	H12A—C12—H12B	109.5
C1—C2—H2	120.8	S1—C12—H12C	109.5
C3—C2—H2	120.8	H12A—C12—H12C	109.5
C4—C3—C2	119.0 (5)	H12B—C12—H12C	109.5
C4—C3—H3	120.5	C5—N1—C1	117.9 (4)
C2—C3—H3	120.5	C5—N1—In1	125.2 (3)
C3—C4—C5	120.5 (4)	C1—N1—In1	116.2 (3)
C3—C4—H4	119.7	C6—N2—C5	129.8 (4)
C5—C4—H4	119.7	C6—N2—H2B	115.1
N1—C5—C4	121.2 (4)	C5—N2—H2B	115.1
N1—C5—N2	119.5 (4)	C6—N3—C10	118.0 (4)
C4—C5—N2	119.3 (4)	C6—N3—In1	125.2 (3)
N3—C6—N2	120.7 (4)	C10—N3—In1	116.7 (3)
N3—C6—C7	121.2 (4)	S1—O1—In1	121.04 (19)
N2—C6—C7	118.0 (4)	O1—In1—N3	83.32 (13)
C8—C7—C6	119.6 (4)	O1—In1—N1	85.12 (13)
C8—C7—H7	120.2	N3—In1—N1	79.63 (13)
C6—C7—H7	120.2	O1—In1—Cl1	89.31 (9)
C7—C8—C9	119.0 (5)	N3—In1—Cl1	93.18 (10)
C7—C8—H8	120.5	N1—In1—Cl1	171.37 (10)
C9—C8—H8	120.5	O1—In1—Cl2	89.15 (9)
C10—C9—C8	118.5 (5)	N3—In1—Cl2	168.87 (10)
C10—C9—H9	120.8	N1—In1—Cl2	91.60 (10)
C8—C9—H9	120.8	Cl1—In1—Cl2	94.92 (5)
N3—C10—C9	123.4 (4)	O1—In1—Cl3	171.97 (9)
N3—C10—H10	118.3	N3—In1—Cl3	90.74 (10)
C9—C10—H10	118.3	N1—In1—Cl3	88.50 (10)
S1—C11—H11A	109.5	Cl1—In1—Cl3	96.44 (5)
S1—C11—H11B	109.5	Cl2—In1—Cl3	95.91 (5)
H11A—C11—H11B	109.5	O1—S1—C12	103.1 (3)
S1—C11—H11C	109.5	O1—S1—C11	106.0 (3)
H11A—C11—H11C	109.5	C12—S1—C11	98.9 (4)
N1—C1—C2—C3	−0.7 (9)	C9—C10—N3—In1	172.6 (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—N1	3.8 (8)	S1—O1—In1—Cl1	138.0 (2)
C3—C4—C5—N2	−176.7 (5)	S1—O1—In1—Cl2	43.1 (2)
N3—C6—C7—C8	−4.3 (8)	C6—N3—In1—O1	53.4 (4)
N2—C6—C7—C8	175.6 (5)	C10—N3—In1—O1	−123.6 (3)
C6—C7—C8—C9	0.1 (8)	C6—N3—In1—N1	−32.9 (4)
C7—C8—C9—C10	1.7 (8)	C10—N3—In1—N1	150.2 (4)
C8—C9—C10—N3	0.5 (8)	C6—N3—In1—Cl1	142.3 (4)
C4—C5—N1—C1	−5.0 (7)	C10—N3—In1—Cl1	−34.6 (3)
N2—C5—N1—C1	175.5 (4)	C6—N3—In1—Cl2	5.6 (8)
C4—C5—N1—In1	165.3 (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—C5	3.5 (8)	C10—N3—In1—Cl3	61.9 (3)
C2—C1—N1—In1	−167.6 (4)	C5—N1—In1—O1	−48.7 (4)
N3—C6—N2—C5	35.4 (8)	C1—N1—In1—O1	121.6 (4)
C7—C6—N2—C5	−144.5 (5)	C5—N1—In1—N3	35.3 (4)
N1—C5—N2—C6	−32.5 (7)	C1—N1—In1—N3	−154.3 (4)
C4—C5—N2—C6	147.9 (5)	C5—N1—In1—Cl2	−137.7 (4)
N2—C6—N3—C10	−173.5 (4)	C1—N1—In1—Cl2	32.6 (4)
C7—C6—N3—C10	6.4 (7)	C5—N1—In1—Cl3	126.4 (4)
N2—C6—N3—In1	9.6 (6)	C1—N1—In1—Cl3	−63.2 (4)
C7—C6—N3—In1	−170.5 (3)	In1—O1—S1—C12	153.0 (3)
C9—C10—N3—C6	−4.5 (7)	In1—O1—S1—C11	−103.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···Cl2i	0.96	2.74	3.499 (8)	137

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) .