Trichlorido(5,5'-dimethyl-2,2'-bipyridine-κN,N')(methanol-κO)indium(III).

In the mol-ecule of the title compound, [InCl(3)(C(12)H(12)N(2))(CH(4)O)], the In(III) atom is six-coordinated in a distorted octa-hedral configuration by two N atoms from the chelating 5,5'-dimethyl-2,2'-bipyridine ligand, one O atom from a methanol molecule and three Cl atoms. In the crystal structure, inter-molecular O-H⋯Cl hydrogen bonds link the mol-ecules into chains parallel to [001].

Related literature

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

Experimental

Crystal data

[InCl3(C12H12N2)(CH4O)]

M = 437.45

Monoclinic,

a = 10.9080 (6) Å

b = 11.2087 (7) Å

c = 13.3584 (8) Å

β = 107.211 (4)°

V = 1560.12 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.02 mm−1

T = 120 (2) K

0.17 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.729, T max = 0.820

12144 measured reflections

4185 independent reflections

3716 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.062

S = 1.15

4185 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −0.68 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803119X/hk2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803119X/hk2541Isup2.hkl

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

[InCl3(C12H12N2)(CH4O)]	F(000) = 864
Mr = 437.45	Dx = 1.862 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1324 reflections
a = 10.9080 (6) Å	θ = 2.0–29.2°
b = 11.2087 (7) Å	µ = 2.02 mm−1
c = 13.3584 (8) Å	T = 120 K
β = 107.211 (4)°	Block, colorless
V = 1560.12 (16) Å3	0.17 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4185 independent reflections
Radiation source: fine-focus sealed tube	3716 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 29.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −14→14
Tmin = 0.729, Tmax = 0.820	k = −15→15
12144 measured reflections	l = −14→18

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0209P)2 + 1.9934P] where P = (Fo2 + 2Fc2)/3
4185 reflections	(Δ/σ)max = 0.017
185 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.68 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	0.773908 (15)	0.320581 (14)	−0.004168 (13)	0.01003 (5)
Cl1	0.87230 (6)	0.29569 (5)	−0.14993 (5)	0.01500 (11)
Cl2	0.55271 (5)	0.31788 (6)	−0.11430 (5)	0.01766 (12)
Cl3	0.79945 (6)	0.53204 (5)	0.02679 (5)	0.01588 (11)
O1	0.69912 (19)	0.30834 (17)	0.13936 (16)	0.0178 (4)
H1B	0.740 (4)	0.280 (4)	0.197 (4)	0.036 (11)*
N1	0.7811 (2)	0.11891 (18)	0.01880 (17)	0.0126 (4)
N2	0.97004 (19)	0.27552 (18)	0.10949 (16)	0.0109 (4)
C1	0.6867 (2)	0.0450 (2)	−0.0335 (2)	0.0152 (5)
H1	0.6098	0.0782	−0.0740	0.018*
C2	0.6982 (3)	−0.0788 (2)	−0.0299 (2)	0.0160 (5)
C3	0.5882 (3)	−0.1568 (2)	−0.0885 (2)	0.0222 (5)
H3A	0.5655	−0.1386	−0.1619	0.027*
H3B	0.5158	−0.1426	−0.0632	0.027*
H3C	0.6132	−0.2391	−0.0777	0.027*
C4	0.8152 (3)	−0.1254 (2)	0.0288 (2)	0.0172 (5)
H4	0.8282	−0.2075	0.0310	0.021*
C5	0.9129 (2)	−0.0502 (2)	0.0843 (2)	0.0161 (5)
H5	0.9908	−0.0815	0.1247	0.019*
C6	0.8929 (2)	0.0732 (2)	0.07869 (19)	0.0123 (4)
C7	0.9932 (2)	0.1588 (2)	0.13432 (19)	0.0117 (4)
C8	1.1071 (2)	0.1235 (2)	0.2067 (2)	0.0154 (5)
H8	1.1202	0.0440	0.2269	0.018*
C9	1.2017 (2)	0.2081 (2)	0.2486 (2)	0.0151 (5)
H9	1.2782	0.1852	0.2974	0.018*
C10	1.1821 (2)	0.3271 (2)	0.21787 (19)	0.0136 (4)
C11	1.2857 (2)	0.4191 (2)	0.2546 (2)	0.0171 (5)
H11A	1.2565	0.4812	0.2914	0.020*
H11B	1.3060	0.4525	0.1952	0.020*
H11C	1.3610	0.3824	0.3006	0.020*
C12	1.0617 (2)	0.3568 (2)	0.15016 (19)	0.0137 (4)
H12	1.0442	0.4365	0.1324	0.016*
C13	0.6145 (3)	0.3950 (2)	0.1646 (2)	0.0186 (5)
H13A	0.5359	0.3991	0.1083	0.022*
H13B	0.6552	0.4718	0.1744	0.022*
H13C	0.5963	0.3715	0.2278	0.022*

	U11	U22	U33	U12	U13	U23
In1	0.00974 (8)	0.00875 (8)	0.00997 (8)	0.00064 (6)	0.00040 (5)	0.00051 (6)
Cl1	0.0161 (3)	0.0161 (3)	0.0129 (3)	0.0011 (2)	0.0044 (2)	−0.0003 (2)
Cl2	0.0119 (2)	0.0182 (3)	0.0186 (3)	0.0012 (2)	−0.0019 (2)	0.0003 (2)
Cl3	0.0203 (3)	0.0100 (2)	0.0166 (3)	−0.0002 (2)	0.0043 (2)	−0.0008 (2)
O1	0.0205 (9)	0.0188 (9)	0.0152 (9)	0.0059 (7)	0.0071 (7)	0.0035 (7)
N1	0.0118 (9)	0.0110 (9)	0.0136 (10)	−0.0003 (7)	0.0015 (8)	0.0011 (7)
N2	0.0111 (9)	0.0103 (8)	0.0102 (9)	−0.0003 (7)	0.0017 (7)	0.0009 (7)
C1	0.0161 (11)	0.0140 (11)	0.0152 (12)	−0.0024 (9)	0.0038 (9)	−0.0015 (9)
C2	0.0211 (12)	0.0132 (11)	0.0154 (11)	−0.0040 (9)	0.0080 (10)	−0.0008 (9)
C3	0.0250 (13)	0.0181 (12)	0.0230 (14)	−0.0078 (10)	0.0062 (11)	−0.0056 (10)
C4	0.0246 (13)	0.0096 (10)	0.0204 (13)	−0.0005 (9)	0.0112 (10)	0.0004 (9)
C5	0.0177 (11)	0.0128 (10)	0.0181 (12)	0.0048 (9)	0.0059 (10)	0.0038 (9)
C6	0.0125 (11)	0.0128 (10)	0.0116 (11)	0.0017 (8)	0.0035 (9)	0.0016 (8)
C7	0.0124 (10)	0.0124 (10)	0.0106 (10)	0.0012 (8)	0.0037 (8)	0.0019 (8)
C8	0.0147 (11)	0.0136 (11)	0.0166 (12)	0.0030 (9)	0.0025 (9)	0.0033 (9)
C9	0.0119 (10)	0.0189 (11)	0.0127 (11)	0.0020 (9)	0.0006 (9)	0.0022 (9)
C10	0.0131 (10)	0.0164 (11)	0.0111 (10)	−0.0009 (9)	0.0033 (8)	−0.0015 (9)
C11	0.0124 (11)	0.0211 (12)	0.0149 (12)	−0.0022 (9)	−0.0004 (9)	0.0005 (10)
C12	0.0139 (11)	0.0150 (10)	0.0117 (11)	0.0010 (8)	0.0030 (9)	0.0023 (9)
C13	0.0183 (12)	0.0173 (11)	0.0227 (13)	0.0012 (9)	0.0098 (10)	−0.0030 (10)

In1—Cl1	2.5015 (6)	C6—N1	1.347 (3)
In1—Cl2	2.4262 (6)	C6—C7	1.479 (3)
In1—Cl3	2.4080 (6)	C7—N2	1.355 (3)
In1—O1	2.2991 (19)	C7—C8	1.387 (3)
In1—N1	2.279 (2)	C8—C9	1.391 (4)
In1—N2	2.284 (2)	C8—H8	0.9300
O1—H1B	0.83 (5)	C9—C10	1.394 (4)
C1—N1	1.345 (3)	C9—H9	0.9300
C1—C2	1.393 (3)	C10—C12	1.397 (3)
C1—H1	0.9300	C10—C11	1.501 (3)
C2—C4	1.387 (4)	C11—H11A	0.9600
C2—C3	1.504 (4)	C11—H11B	0.9600
C3—H3A	0.9600	C11—H11C	0.9600
C3—H3B	0.9600	C12—N2	1.343 (3)
C3—H3C	0.9600	C12—H12	0.9300
C4—C5	1.389 (4)	C13—O1	1.447 (3)
C4—H4	0.9300	C13—H13A	0.9600
C5—C6	1.399 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
Cl2—In1—Cl1	96.05 (2)	C2—C4—C5	120.4 (2)
Cl3—In1—Cl1	100.89 (2)	C2—C4—H4	119.8
Cl3—In1—Cl2	99.22 (2)	C5—C4—H4	119.8
O1—In1—Cl1	169.20 (5)	C4—C5—C6	119.2 (2)
O1—In1—Cl2	88.30 (5)	C4—C5—H5	120.4
O1—In1—Cl3	88.11 (5)	C6—C5—H5	120.4
N1—In1—Cl1	89.35 (5)	N1—C6—C5	120.5 (2)
N1—In1—Cl2	93.30 (5)	N1—C6—C7	117.2 (2)
N1—In1—Cl3	162.82 (6)	C5—C6—C7	122.3 (2)
N1—In1—O1	80.51 (7)	N2—C7—C8	120.6 (2)
N1—In1—N2	72.73 (7)	N2—C7—C6	116.6 (2)
N2—In1—Cl1	87.68 (5)	C8—C7—C6	122.8 (2)
N2—In1—Cl2	165.54 (5)	C7—C8—C9	119.4 (2)
N2—In1—Cl3	93.76 (5)	C7—C8—H8	120.3
N2—In1—O1	85.77 (7)	C9—C8—H8	120.3
In1—O1—H1B	125 (3)	C8—C9—C10	120.2 (2)
C13—O1—In1	124.22 (16)	C8—C9—H9	119.9
C13—O1—H1B	104 (3)	C10—C9—H9	119.9
C1—N1—In1	123.41 (17)	C9—C10—C12	116.8 (2)
C1—N1—C6	119.6 (2)	C9—C10—C11	121.8 (2)
C6—N1—In1	116.52 (16)	C12—C10—C11	121.4 (2)
C7—N2—In1	116.51 (16)	C10—C11—H11A	109.5
C12—N2—In1	123.91 (16)	C10—C11—H11B	109.5
C12—N2—C7	119.6 (2)	H11A—C11—H11B	109.5
N1—C1—C2	123.3 (3)	C10—C11—H11C	109.5
N1—C1—H1	118.4	H11A—C11—H11C	109.5
C2—C1—H1	118.4	H11B—C11—H11C	109.5
C4—C2—C1	116.9 (2)	N2—C12—C10	123.1 (2)
C4—C2—C3	122.3 (2)	N2—C12—H12	118.5
C1—C2—C3	120.8 (3)	C10—C12—H12	118.5
C2—C3—H3A	109.5	O1—C13—H13A	109.5
C2—C3—H3B	109.5	O1—C13—H13B	109.5
H3A—C3—H3B	109.5	H13A—C13—H13B	109.5
C2—C3—H3C	109.5	O1—C13—H13C	109.5
H3A—C3—H3C	109.5	H13A—C13—H13C	109.5
H3B—C3—H3C	109.5	H13B—C13—H13C	109.5
N1—In1—O1—C13	−152.9 (2)	N1—C1—C2—C3	178.8 (2)
N2—In1—O1—C13	133.9 (2)	C1—C2—C4—C5	2.5 (4)
Cl3—In1—O1—C13	40.01 (19)	C3—C2—C4—C5	−178.0 (2)
Cl2—In1—O1—C13	−59.27 (19)	C2—C4—C5—C6	−1.2 (4)
Cl1—In1—O1—C13	−173.3 (2)	C4—C5—C6—N1	−1.2 (4)
N2—In1—N1—C1	−175.9 (2)	C4—C5—C6—C7	−179.1 (2)
O1—In1—N1—C1	95.6 (2)	C5—C6—N1—C1	2.0 (4)
Cl3—In1—N1—C1	144.79 (17)	C7—C6—N1—C1	−180.0 (2)
Cl2—In1—N1—C1	7.9 (2)	C5—C6—N1—In1	−170.21 (19)
Cl1—In1—N1—C1	−88.11 (19)	C7—C6—N1—In1	7.8 (3)
N2—In1—N1—C6	−3.99 (17)	N1—C6—C7—N2	−8.3 (3)
O1—In1—N1—C6	−92.48 (18)	C5—C6—C7—N2	169.6 (2)
Cl3—In1—N1—C6	−43.3 (3)	N1—C6—C7—C8	173.2 (2)
Cl2—In1—N1—C6	179.80 (17)	C5—C6—C7—C8	−8.9 (4)
Cl1—In1—N1—C6	83.78 (17)	C8—C7—N2—C12	4.4 (4)
N1—In1—N2—C12	178.2 (2)	C6—C7—N2—C12	−174.2 (2)
O1—In1—N2—C12	−100.4 (2)	C8—C7—N2—In1	−176.82 (18)
Cl3—In1—N2—C12	−12.60 (19)	C6—C7—N2—In1	4.6 (3)
Cl2—In1—N2—C12	−166.46 (16)	N2—C7—C8—C9	−4.3 (4)
Cl1—In1—N2—C12	88.17 (19)	C6—C7—C8—C9	174.2 (2)
N1—In1—N2—C7	−0.55 (16)	C7—C8—C9—C10	−0.2 (4)
O1—In1—N2—C7	80.81 (17)	C8—C9—C10—C12	4.4 (4)
Cl3—In1—N2—C7	168.64 (17)	C8—C9—C10—C11	−174.9 (2)
Cl2—In1—N2—C7	14.8 (3)	C9—C10—C12—N2	−4.5 (4)
Cl1—In1—N2—C7	−90.59 (17)	C11—C10—C12—N2	174.9 (2)
C2—C1—N1—C6	−0.5 (4)	C10—C12—N2—C7	0.1 (4)
C2—C1—N1—In1	171.1 (2)	C10—C12—N2—In1	−178.61 (18)
N1—C1—C2—C4	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Cl1i	0.83 (5)	2.29 (5)	3.115 (2)	174 (4)

In1—Cl1	2.5015 (6)
In1—Cl2	2.4262 (6)
In1—Cl3	2.4080 (6)
In1—O1	2.2991 (19)
In1—N1	2.279 (2)
In1—N2	2.284 (2)

Cl2—In1—Cl1	96.05 (2)
Cl3—In1—Cl1	100.89 (2)
Cl3—In1—Cl2	99.22 (2)
O1—In1—Cl1	169.20 (5)
O1—In1—Cl2	88.30 (5)
O1—In1—Cl3	88.11 (5)
N1—In1—Cl1	89.35 (5)
N1—In1—Cl2	93.30 (5)
N1—In1—Cl3	162.82 (6)
N1—In1—O1	80.51 (7)
N1—In1—N2	72.73 (7)
N2—In1—Cl1	87.68 (5)
N2—In1—Cl2	165.54 (5)
N2—In1—Cl3	93.76 (5)
N2—In1—O1	85.77 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯Cl1i	0.83 (5)	2.29 (5)	3.115 (2)	174 (4)

Symmetry code: (i) .