Trichlorido(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')(methanol-κO)indium(III) methanol monosolvate.

In the title compound, [InCl(3)(C(12)H(12)N(2))(CH(3)OH)]·CH(3)OH, the In(III) atom is six-coordinated in a distorted octa-hedral geometry by two N atoms from a chelating 4,4'-dimethyl-2,2'-bipyridine ligand, one O atom from a methanol mol-ecule and three Cl atoms. In the crystal, inter-molecular O-H⋯O and O-H⋯Cl hydrogen bonds link the complex and solvent methanol mol-ecules. Intra-molecular C-H⋯Cl hydrogen bonds are also present in the complex.

Related literature

For related structures, see: Abedi et al. (2012 ▶); Ahmadi et al. (2008 ▶); Alizadeh et al. (2010 ▶); Amani et al. (2009 ▶); Dong et al. (1987 ▶); Hojjat Kashani et al. (2008 ▶); Ilyuhin & Malyarick (1994 ▶); Kalateh, Ahmadi et al. (2008 ▶); Kalateh, Ebadi et al. (2008 ▶); Kalateh et al. (2010 ▶); Malyarick et al. (1992 ▶); Shirvan & Haydari Dezfuli (2011 ▶, 2012 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[InCl3(C12H12N2)(CH4O)]·CH4O

M = 469.49

Monoclinic,

a = 12.0318 (6) Å

b = 10.3751 (4) Å

c = 15.2626 (7) Å

β = 91.981 (4)°

V = 1904.11 (15) Å3

Z = 4

Mo Kα radiation

μ = 1.67 mm−1

T = 298 K

0.30 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.621, T max = 0.699

11231 measured reflections

3747 independent reflections

3200 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.05

3747 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.43 e Å−3

Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ▶; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035490/hy2578sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035490/hy2578Isup2.hkl

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

[InCl3(C12H12N2)(CH4O)]·CH4O	F(000) = 936
Mr = 469.49	Dx = 1.638 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11231 reflections
a = 12.0318 (6) Å	θ = 1.7–26.0°
b = 10.3751 (4) Å	µ = 1.67 mm−1
c = 15.2626 (7) Å	T = 298 K
β = 91.981 (4)°	Block, colorless
V = 1904.11 (15) Å3	0.30 × 0.25 × 0.23 mm
Z = 4

Bruker APEXII CCD diffractometer	3747 independent reflections
Radiation source: fine-focus sealed tube	3200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.621, Tmax = 0.699	k = −12→12
11231 measured reflections	l = −18→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.029P] where P = (Fo2 + 2Fc2)/3
3747 reflections	(Δ/σ)max = 0.009
205 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −0.76 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	0.760984 (19)	0.07129 (2)	0.223229 (16)	0.03869 (11)
C1	0.5479 (3)	−0.0469 (4)	0.3156 (3)	0.0454 (9)
H1	0.5727	−0.1222	0.2897	0.054*
C2	0.4532 (3)	−0.0517 (4)	0.3638 (3)	0.0484 (9)
H2	0.4158	−0.1293	0.3705	0.058*
C3	0.4143 (3)	0.0591 (4)	0.4021 (3)	0.0459 (9)
C4	0.3089 (4)	0.0606 (5)	0.4526 (3)	0.0641 (12)
H4A	0.2564	0.1185	0.4248	0.077*
H4B	0.3253	0.0889	0.5115	0.077*
H4C	0.2779	−0.0246	0.4537	0.077*
C5	0.4753 (3)	0.1719 (4)	0.3912 (2)	0.0440 (8)
H5	0.4517	0.2485	0.4162	0.053*
C6	0.5711 (3)	0.1703 (3)	0.3433 (2)	0.0350 (7)
C7	0.6408 (3)	0.2864 (3)	0.3311 (2)	0.0344 (7)
C8	0.6183 (3)	0.4038 (3)	0.3701 (2)	0.0407 (8)
H8	0.5564	0.4125	0.4044	0.049*
C9	0.6881 (3)	0.5084 (3)	0.3578 (2)	0.0456 (8)
C10	0.6694 (4)	0.6323 (4)	0.4057 (3)	0.0684 (13)
H10A	0.6741	0.6169	0.4678	0.082*
H10B	0.5971	0.6656	0.3897	0.082*
H10C	0.7252	0.6938	0.3904	0.082*
C11	0.7760 (3)	0.4922 (4)	0.3035 (3)	0.0518 (9)
H11	0.8233	0.5608	0.2925	0.062*
C12	0.7935 (3)	0.3735 (4)	0.2654 (3)	0.0494 (9)
H12	0.8525	0.3642	0.2281	0.059*
C13	0.9285 (5)	−0.0471 (6)	0.3806 (5)	0.094 (2)
H13A	0.9916	−0.0296	0.3457	0.113*
H13B	0.9018	−0.1327	0.3684	0.113*
H13C	0.9500	−0.0404	0.4416	0.113*
C14	0.9904 (6)	0.3073 (8)	0.4407 (5)	0.121 (3)
H14A	0.9729	0.3965	0.4312	0.182*
H14B	1.0182	0.2709	0.3880	0.182*
H14C	1.0459	0.2998	0.4871	0.182*
N1	0.6052 (2)	0.0611 (3)	0.3047 (2)	0.0380 (6)
N2	0.7290 (2)	0.2717 (3)	0.28000 (18)	0.0381 (6)
O1	0.8436 (3)	0.0429 (3)	0.3603 (2)	0.0572 (8)
H1B	0.844 (5)	0.109 (6)	0.393 (4)	0.083 (18)*
O2	0.8937 (4)	0.2405 (5)	0.4641 (3)	0.1071 (15)
H2B	0.8716	0.2694	0.5104	0.161*
Cl1	0.65354 (13)	0.12400 (14)	0.08916 (7)	0.0776 (4)
Cl2	0.76643 (9)	−0.15957 (10)	0.20171 (9)	0.0639 (3)
Cl3	0.94145 (10)	0.13256 (13)	0.17180 (10)	0.0777 (4)

	U11	U22	U33	U12	U13	U23
In1	0.04584 (16)	0.03230 (16)	0.03823 (16)	0.00351 (10)	0.00593 (10)	−0.00244 (10)
C1	0.055 (2)	0.0314 (18)	0.050 (2)	−0.0074 (15)	−0.0027 (17)	−0.0017 (15)
C2	0.053 (2)	0.043 (2)	0.049 (2)	−0.0145 (16)	0.0001 (17)	0.0010 (17)
C3	0.0499 (19)	0.050 (2)	0.0383 (19)	−0.0082 (16)	0.0037 (15)	0.0011 (16)
C4	0.065 (3)	0.066 (3)	0.063 (3)	−0.015 (2)	0.019 (2)	−0.001 (2)
C5	0.0528 (19)	0.0374 (19)	0.0423 (19)	−0.0021 (15)	0.0097 (15)	−0.0041 (16)
C6	0.0446 (16)	0.0293 (16)	0.0310 (16)	−0.0010 (13)	−0.0014 (13)	0.0003 (13)
C7	0.0441 (16)	0.0294 (16)	0.0296 (15)	−0.0001 (13)	0.0005 (12)	0.0001 (13)
C8	0.0510 (18)	0.0347 (18)	0.0368 (18)	−0.0004 (15)	0.0062 (15)	−0.0010 (15)
C9	0.062 (2)	0.0288 (18)	0.046 (2)	−0.0016 (16)	−0.0024 (17)	0.0004 (16)
C10	0.094 (3)	0.034 (2)	0.079 (3)	−0.007 (2)	0.010 (3)	−0.010 (2)
C11	0.055 (2)	0.033 (2)	0.068 (3)	−0.0083 (17)	0.0037 (19)	0.0033 (19)
C12	0.0480 (19)	0.040 (2)	0.061 (2)	−0.0027 (16)	0.0139 (18)	0.0007 (18)
C13	0.095 (4)	0.090 (4)	0.095 (4)	0.046 (3)	−0.033 (3)	−0.009 (3)
C14	0.106 (5)	0.128 (7)	0.128 (6)	−0.039 (5)	−0.015 (4)	0.048 (5)
N1	0.0435 (14)	0.0322 (15)	0.0381 (15)	−0.0012 (11)	−0.0018 (12)	−0.0026 (12)
N2	0.0452 (15)	0.0282 (15)	0.0411 (15)	−0.0007 (11)	0.0057 (12)	−0.0019 (12)
O1	0.0683 (18)	0.0521 (17)	0.0504 (17)	0.0180 (14)	−0.0104 (14)	−0.0038 (14)
O2	0.144 (4)	0.099 (3)	0.078 (3)	−0.015 (3)	0.008 (3)	−0.027 (3)
Cl1	0.1109 (9)	0.0774 (8)	0.0431 (6)	0.0324 (7)	−0.0173 (6)	−0.0093 (6)
Cl2	0.0772 (7)	0.0346 (5)	0.0808 (7)	0.0035 (4)	0.0164 (6)	−0.0134 (5)
Cl3	0.0636 (6)	0.0626 (7)	0.1095 (10)	−0.0022 (5)	0.0415 (7)	−0.0084 (7)

In1—Cl1	2.4443 (13)	C9—C10	1.500 (5)
In1—Cl2	2.4188 (11)	C9—C11	1.376 (5)
In1—Cl3	2.4192 (13)	C11—C12	1.381 (6)
In1—O1	2.304 (3)	C1—H1	0.9300
In1—N1	2.287 (3)	C2—H2	0.9300
In1—N2	2.290 (3)	C4—H4B	0.9600
O1—C13	1.411 (7)	C4—H4C	0.9600
O1—H1B	0.85 (6)	C4—H4A	0.9600
O2—C14	1.411 (9)	C5—H5	0.9300
O2—H2B	0.8200	C8—H8	0.9300
N1—C1	1.329 (5)	C10—H10A	0.9600
N1—C6	1.348 (4)	C10—H10C	0.9600
N2—C7	1.347 (4)	C10—H10B	0.9600
N2—C12	1.334 (5)	C11—H11	0.9300
C1—C2	1.378 (6)	C12—H12	0.9300
C2—C3	1.379 (6)	C13—H13C	0.9600
C3—C4	1.507 (6)	C13—H13A	0.9600
C3—C5	1.394 (6)	C13—H13B	0.9600
C5—C6	1.386 (5)	C14—H14A	0.9600
C6—C7	1.483 (5)	C14—H14B	0.9600
C7—C8	1.387 (4)	C14—H14C	0.9600
C8—C9	1.389 (5)
Cl1···Cl2	3.6456 (18)	N2···H1B	2.75 (6)
Cl1···Cl3	3.646 (2)	C1···C7ii	3.579 (5)
Cl1···N1	3.423 (3)	C1···C8ii	3.450 (5)
Cl1···N2	3.387 (3)	C2···C7ii	3.566 (5)
Cl1···C8i	3.368 (3)	C2···C12ii	3.591 (6)
Cl2···O1	3.313 (3)	C5···Cl2iii	3.639 (4)
Cl2···N1	3.419 (3)	C7···C1iii	3.579 (5)
Cl2···C13	3.500 (7)	C7···C2iii	3.566 (5)
Cl2···C5ii	3.639 (4)	C8···C1iii	3.450 (5)
Cl2···Cl1	3.6456 (18)	C8···Cl1v	3.368 (3)
Cl2···C1	3.408 (4)	C12···C2iii	3.591 (6)
Cl3···Cl1	3.646 (2)	C12···C14	3.578 (9)
Cl3···C12	3.411 (4)	C13···O2	3.277 (8)
Cl3···O1	3.281 (3)	C14···Cl3v	3.650 (8)
Cl3···N2	3.411 (3)	C14···C12	3.578 (9)
Cl3···C14i	3.650 (8)	C1···H4Bvi	3.0300
Cl3···O2i	3.462 (5)	C5···H8	2.6900
Cl1···H10Ai	3.1300	C8···H5	2.6800
Cl1···H2Bi	3.1300	C14···H1B	2.79 (6)
Cl1···H8i	3.0400	H1···Cl2	2.7600
Cl1···H2iii	2.7700	H1B···O2	1.83 (6)
Cl1···H10Bii	3.0700	H1B···C14	2.79 (6)
Cl2···H14Biv	3.0600	H1B···H2B	2.4600
Cl2···H13B	2.9900	H2···H4C	2.3900
Cl2···H4Aii	3.0100	H2···Cl1ii	2.7700
Cl2···H1	2.7600	H2B···H1B	2.4600
Cl3···H14Aiv	3.1100	H2B···Cl1v	3.1300
Cl3···H12	2.7800	H2B···Cl3v	2.7700
Cl3···H11iv	2.9600	H4A···Cl2iii	3.0100
Cl3···H2Bi	2.7700	H4B···C1vi	3.0300
O1···Cl2	3.313 (3)	H4C···H2	2.3900
O1···Cl3	3.281 (3)	H5···H8	2.1300
O1···O2	2.648 (6)	H5···C8	2.6800
O1···N1	2.969 (4)	H8···H5	2.1300
O1···N2	2.987 (4)	H8···C5	2.6900
O2···Cl3v	3.462 (5)	H8···Cl1v	3.0400
O2···O1	2.648 (6)	H10A···Cl1v	3.1300
O2···C13	3.277 (8)	H10B···Cl1iii	3.0700
O2···H1B	1.83 (6)	H10C···H11	2.3800
N1···Cl2	3.419 (3)	H11···Cl3vii	2.9600
N1···O1	2.969 (4)	H11···H10C	2.3800
N1···N2	2.678 (4)	H12···H13Avii	2.4800
N1···Cl1	3.423 (3)	H12···Cl3	2.7800
N1···C7	2.408 (4)	H13A···H12iv	2.4800
N2···N1	2.678 (4)	H13B···Cl2	2.9900
N2···Cl1	3.387 (3)	H13C···H13Cviii	2.2800
N2···Cl3	3.411 (3)	H14A···Cl3vii	3.1100
N2···C6	2.403 (4)	H14B···Cl2vii	3.0600
N2···O1	2.987 (4)
Cl1—In1—Cl2	97.12 (5)	C10—C9—C11	122.0 (3)
Cl1—In1—Cl3	97.14 (5)	C9—C11—C12	119.6 (4)
Cl1—In1—O1	171.08 (9)	N2—C12—C11	122.5 (4)
Cl1—In1—N1	92.63 (8)	C2—C1—H1	119.00
Cl1—In1—N2	91.30 (8)	N1—C1—H1	119.00
Cl2—In1—Cl3	100.80 (4)	C3—C2—H2	120.00
Cl2—In1—O1	89.07 (8)	C1—C2—H2	120.00
Cl2—In1—N1	93.13 (8)	C3—C4—H4A	109.00
Cl2—In1—N2	162.96 (8)	C3—C4—H4C	110.00
Cl3—In1—O1	87.96 (9)	H4A—C4—H4B	109.00
Cl3—In1—N1	161.82 (8)	C3—C4—H4B	109.00
Cl3—In1—N2	92.79 (7)	H4B—C4—H4C	109.00
O1—In1—N1	80.58 (11)	H4A—C4—H4C	110.00
O1—In1—N2	81.11 (10)	C3—C5—H5	120.00
N1—In1—N2	71.62 (10)	C6—C5—H5	120.00
In1—O1—C13	124.8 (4)	C9—C8—H8	120.00
C13—O1—H1B	115 (4)	C7—C8—H8	120.00
In1—O1—H1B	115 (4)	C9—C10—H10A	109.00
C14—O2—H2B	109.00	C9—C10—H10C	109.00
In1—N1—C1	123.1 (3)	H10A—C10—H10B	109.00
In1—N1—C6	117.8 (2)	H10A—C10—H10C	109.00
C1—N1—C6	119.2 (3)	H10B—C10—H10C	110.00
C7—N2—C12	118.8 (3)	C9—C10—H10B	110.00
In1—N2—C7	117.9 (2)	C12—C11—H11	120.00
In1—N2—C12	123.3 (2)	C9—C11—H11	120.00
N1—C1—C2	122.6 (4)	N2—C12—H12	119.00
C1—C2—C3	119.7 (4)	C11—C12—H12	119.00
C2—C3—C4	122.0 (4)	O1—C13—H13B	110.00
C4—C3—C5	120.5 (4)	O1—C13—H13C	110.00
C2—C3—C5	117.5 (4)	O1—C13—H13A	109.00
C3—C5—C6	120.2 (4)	H13A—C13—H13C	109.00
N1—C6—C7	116.5 (3)	H13B—C13—H13C	109.00
N1—C6—C5	120.8 (3)	H13A—C13—H13B	109.00
C5—C6—C7	122.7 (3)	O2—C14—H14A	109.00
N2—C7—C6	116.2 (3)	O2—C14—H14B	109.00
N2—C7—C8	121.2 (3)	O2—C14—H14C	109.00
C6—C7—C8	122.7 (3)	H14A—C14—H14B	110.00
C7—C8—C9	120.0 (3)	H14A—C14—H14C	109.00
C8—C9—C11	117.8 (3)	H14B—C14—H14C	109.00
C8—C9—C10	120.2 (3)
Cl2—In1—O1—C13	38.9 (4)	C1—N1—C6—C7	178.0 (3)
Cl3—In1—O1—C13	−62.0 (4)	In1—N2—C12—C11	−176.9 (3)
N1—In1—O1—C13	132.2 (4)	C7—N2—C12—C11	2.7 (6)
N2—In1—O1—C13	−155.1 (4)	In1—N2—C7—C8	177.9 (2)
Cl1—In1—N1—C1	90.5 (3)	In1—N2—C7—C6	−1.6 (4)
Cl1—In1—N1—C6	−89.8 (2)	C12—N2—C7—C6	178.8 (3)
Cl2—In1—N1—C1	−6.8 (3)	C12—N2—C7—C8	−1.7 (5)
Cl2—In1—N1—C6	173.0 (2)	N1—C1—C2—C3	0.6 (7)
O1—In1—N1—C1	−95.4 (3)	C1—C2—C3—C5	−1.2 (6)
O1—In1—N1—C6	84.4 (2)	C1—C2—C3—C4	177.6 (4)
N2—In1—N1—C1	−179.0 (3)	C2—C3—C5—C6	0.1 (6)
N2—In1—N1—C6	0.7 (2)	C4—C3—C5—C6	−178.8 (4)
Cl1—In1—N2—C7	92.9 (2)	C3—C5—C6—C7	−178.6 (3)
Cl1—In1—N2—C12	−87.6 (3)	C3—C5—C6—N1	1.8 (5)
Cl3—In1—N2—C7	−169.9 (2)	C5—C6—C7—N2	−177.4 (3)
Cl3—In1—N2—C12	9.7 (3)	C5—C6—C7—C8	3.1 (5)
O1—In1—N2—C7	−82.4 (2)	N1—C6—C7—N2	2.3 (4)
O1—In1—N2—C12	97.1 (3)	N1—C6—C7—C8	−177.2 (3)
N1—In1—N2—C7	0.5 (2)	C6—C7—C8—C9	178.6 (3)
N1—In1—N2—C12	−179.9 (3)	N2—C7—C8—C9	−0.9 (5)
In1—N1—C1—C2	−179.1 (3)	C7—C8—C9—C11	2.6 (5)
C6—N1—C1—C2	1.2 (6)	C7—C8—C9—C10	−175.0 (3)
In1—N1—C6—C5	177.9 (2)	C8—C9—C11—C12	−1.7 (6)
C1—N1—C6—C5	−2.4 (5)	C10—C9—C11—C12	175.9 (4)
In1—N1—C6—C7	−1.8 (4)	C9—C11—C12—N2	−1.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2	0.85 (6)	1.83 (6)	2.648 (6)	161 (6)
O2—H2B···Cl3v	0.82	2.77	3.462 (5)	143
C1—H1···Cl2	0.93	2.76	3.408 (4)	128
C2—H2···Cl1ii	0.93	2.77	3.681 (4)	167
C12—H12···Cl3	0.93	2.78	3.411 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2	0.85 (6)	1.83 (6)	2.648 (6)	161 (6)
O2—H2B⋯Cl3i	0.82	2.77	3.462 (5)	143
C1—H1⋯Cl2	0.93	2.76	3.408 (4)	128
C2—H2⋯Cl1ii	0.93	2.77	3.681 (4)	167
C12—H12⋯Cl3	0.93	2.78	3.411 (4)	126

Symmetry codes: (i) ; (ii) .