Trichlorido(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)(methanol-κO)indium(III) methanol monosolvate

Shirvan, S.A.; Haydari Dezfuli, S.

doi:10.1107/S1600536812035490

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages m1189-m1190

doi:10.1107/S1600536812035490

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Trichlorido(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)(methanol-κO)indium(III) methanol monosolvate

Sadif A. Shirvan ^a ^* and Sara Haydari Dezfuli ^a

^aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran
^*Correspondence e-mail: sadif_shirvan1@yahoo.com

(Received 2 August 2012; accepted 11 August 2012; online 23 August 2012)

In the title compound, [InCl₃(C₁₂H₁₂N₂)(CH₃OH)]·CH₃OH, the In^III atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating 4,4′-dimethyl-2,2′-bipyridine ligand, one O atom from a methanol molecule and three Cl atoms. In the crystal, intermolecular O—H⋯O and O—H⋯Cl hydrogen bonds link the complex and solvent methanol molecules. Intramolecular 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_r = 469.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.05
3747 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.43 e Å⁻³
Δρ_min = −0.76 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812035490/hy2578sup1.cif

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

checkCIF report

Comment top

Several In(III) complexes with a formula [In(L₁)Cl₃(L₂)] (L₁ = an N,N'-chelating ligand, L₂ = DMSO, H₂O, MeOH and EtOH), such as [In(bipy)Cl₃(H₂O)], (II), [In(bipy)Cl₃(EtOH)], (III), [In(bipy)Cl₃(H₂O)].H₂O, (IV) (Malyarick et al., 1992), [In(phen)Cl₃(DMSO)], (V) (Dong et al., 1987), [In(phen)Cl₃(H₂O)], (VI), [In(phen)Cl₃(EtOH)].EtOH, (VII) (Ilyuhin & Malyarick, 1994), [In(4,4'-dmbipy)Cl₃(DMSO)], (IIX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl₃(MeOH)], (IX) (Kalateh, Ahmadi et al., 2008), [In(4bt)Cl₃(MeOH)], (X), and [In(4bt)Cl₃(DMSO)], (XI) (Abedi et al., 2012) (bipy = 2,2'-bipyridine, phen = 1,10-phenanthroline, DMSO = dimethyl sulfoxide, 4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbipy = 5,5'-dimethyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. 4,4'-Dmbipy is a good bidentate ligand, and numerous complexes with 4,4'-dmbipy have been prepared, such as that of [Hg(4,4'-dmbipy)I₂], (XII) (Yousefi et al., 2008), [Hg(4,4'-dmbipy)Br₂], (XIII) (Kalateh, Ebadi et al., 2008), [Fe(4,4'-dmbipy)Cl₃(DMSO)], (XIV) (Amani et al., 2009), [Pt(4,4'-dmbipy)Cl₄], (XV) (Hojjat Kashani et al., 2008), [Cd(4,4'-dmbipy)I₂(DMSO)], (XVI) (Kalateh et al., 2010), [Zn(4,4'-dmbipy)Br₂], (XVII) (Alizadeh et al., 2010), [Zn(4,4'-dmbipy)(H₂O)(NO₃)₂], (XVIII) (Shirvan & Haydari Dezfuli, 2011), and [Cd(4,4'-dmbipy)Br₂(DMSO)], (XIX) (Shirvan & Haydari Dezfuli, 2012). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the In^III atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating 4,4'-dmbipy ligand, one O atom from a methanol molecule and three Cl atoms. There is also one solvent methanol molecule in the asymmetric unit. The In—Cl, In—N and In—O bond lengths and angles are within normal range. In the crystal, intermolecular O—H···O and O—H···Cl hydrogen bonds link the complex and solvent methanol molecules (Fig. 2, Table 1). Intramolecular C—H···Cl hydrogen bonds are present in the complex.

Related literature top

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 top

For the preparation of the title compound, a solution of 4,4'-dmbipy (0.30 g, 1.65 mmol) in methanol (20 ml) was added to a solution of InCl₃.4H₂O (0.48 g, 1.65 mmol) in methanol (20 ml). The resulting colorless solution was stirred for 10 min at room temperature and then it was left to evaporate slowly at room temperature. After six days, colorless block crystals of the title compound were isolated (yield: 0.62 g, 80.0%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Trichlorido(4,4'-dimethyl-2,2'-bipyridine-κ²N,N')(methanol- κO)indium(III) methanol monosolvate top

Crystal data top

[InCl₃(C₁₂H₁₂N₂)(CH₄O)]·CH₄O	F(000) = 936
M_r = 469.49	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	3747 independent reflections
Radiation source: fine-focus sealed tube	3200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
T_min = 0.621, T_max = 0.699	k = −12→12
11231 measured reflections	l = −18→18

Refinement top

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(F_o²) + (0.0645P)² + 0.029P] where P = (F_o² + 2F_c²)/3
3747 reflections	(Δ/σ)_max = 0.009
205 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

[InCl₃(C₁₂H₁₂N₂)(CH₄O)]·CH₄O	V = 1904.11 (15) Å³
M_r = 469.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0318 (6) Å	µ = 1.67 mm⁻¹
b = 10.3751 (4) Å	T = 298 K
c = 15.2626 (7) Å	0.30 × 0.25 × 0.23 mm
β = 91.981 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3747 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3200 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.699	R_int = 0.064
11231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.43 e Å⁻³
3747 reflections	Δρ_min = −0.76 e Å⁻³
205 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···Cl1^v	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···Cl3^v	3.650 (8)
Cl3···N2	3.411 (3)	C14···C12	3.578 (9)
Cl3···C14ⁱ	3.650 (8)	C1···H4B^vi	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···H14B^iv	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···H14A^iv	3.1100	H2B···Cl1^v	3.1300
Cl3···H12	2.7800	H2B···Cl3^v	2.7700
Cl3···H11^iv	2.9600	H4A···Cl2ⁱⁱⁱ	3.0100
Cl3···H2Bⁱ	2.7700	H4B···C1^vi	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···Cl3^v	3.462 (5)	H8···Cl1^v	3.0400
O2···O1	2.648 (6)	H10A···Cl1^v	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···Cl3^vii	2.9600
N1···O1	2.969 (4)	H11···H10C	2.3800
N1···N2	2.678 (4)	H12···H13A^vii	2.4800
N1···Cl1	3.423 (3)	H12···Cl3	2.7800
N1···C7	2.408 (4)	H13A···H12^iv	2.4800
N2···N1	2.678 (4)	H13B···Cl2	2.9900
N2···Cl1	3.387 (3)	H13C···H13C^viii	2.2800
N2···Cl3	3.411 (3)	H14A···Cl3^vii	3.1100
N2···C6	2.403 (4)	H14B···Cl2^vii	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)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+2, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y, −z+1; (vii) −x+2, y+1/2, −z+1/2; (viii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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···Cl3^v	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: (ii) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[InCl₃(C₁₂H₁₂N₂)(CH₄O)]·CH₄O
M_r	469.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.0318 (6), 10.3751 (4), 15.2626 (7)
β (°)	91.981 (4)
V (Å³)	1904.11 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.30 × 0.25 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.621, 0.699
No. of measured, independent and observed [I > 2σ(I)] reflections	11231, 3747, 3200
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.05
No. of reflections	3747
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.43, −0.76

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

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