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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1353-m1354
doi:10.1107/S160053680803119X

Tri­chlorido(5,5′-di­methyl-2,2′-bi­pyridine-κ2N,N′)(methanol-κO)indium(III)

Khadijeh Kalateh,a Roya Ahmadi,a Amin Ebadi,b Vahid Amania* and Hamid Reza Khavasic

aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, bDepartment of Chemistry, Islamic Azad University, Kazeroon Branch, Kazeroon, Fars, Iran, and cDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
*Correspondence e-mail: v_amani2002@yahoo.com

(Received 26 September 2008; accepted 26 September 2008; online 4 October 2008)

In the mol­ecule of the title compound, [InCl3(C12H12N2)(CH4O)], the InIII atom is six-coordinated in a distorted octa­hedral 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, inter­molecular O—H⋯Cl hydrogen bonds link the mol­ecules into chains parallel to [001].

Related literature

For related literature, see: Ahmadi, Kalateh, Ebadi et al. (2008[Ahmadi, R., Kalateh, K., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1266.]); Ahmadi, Khalighi et al. (2008[Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.]); Amani et al. (2007[Amani, V., Safari, N., Khavasi, H. R. & Mirzaei, P. (2007). Polyhedron, 26, 4908-4914.]); Khalighi et al. (2008[Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211-m1212.]); Khavasi et al. (2007[Khavasi, H. R., Amani, V. & Safari, N. (2007). Z. Kristallogr. 222, 155-156.], 2008[Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848-1854.]); Tadayon Pour et al. (2008[Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.]); Yousefi, Rashidi Vahid et al. (2008[Yousefi, M., Rashidi Vahid, R., Amani, V., Arab Chamjangali, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m1339-m1340.]); Yousefi, Tadayon Pour et al. (2008[Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259.]). Yousefi, Khalighi et al. (2008[Yousefi, M., Khalighi, A., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1284-m1285.]). For related structures, see: Ilyukhin & Malyarick (1994[Ilyukhin, A. B. & Malyarick, M. A. (1994). Kristallografiya, 39, 439-443.]); Malyarick et al. (1992[Malyarick, M. A., Petrosyants, S. P. & Ilyukhin, A. B. (1992). Polyhedron, 11, 1067-1073.]); Nan et al. (1987[Nan, D., Naidong, W., Zhenchao, D. & Shengzhi, H. (1987). Jiegou Huaxue, 6, 145-149.]); Ahmadi, Kalateh, Abedi et al. (2008[Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306-m1307.]).

[Scheme 1]

Experimental

Crystal data

  • [InCl3(C12H12N2)(CH4O)]

  • Mr = 437.45

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.729, Tmax = 0.820

  • 12144 measured reflections

  • 4185 independent reflections

  • 3716 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 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

Table 1
Selected geometric parameters (Å, °)

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

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

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

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

checkCIF report


Comment top

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl2], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl2], (III), (Ahmadi, Kalateh et al., 2008), [HgI2(4,4'-dmbpy)], (IV), (Yousefi, Tadayon Pour et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)2]n, (V), (Ahmadi, Khalighi et al., 2008), [Hg(5,5'-dmbpy)I2], (VI), (Tadayon Pour et al., 2008), [Cu(5,5'-dcbpy)(en)(H2O)2].2.5H2O, (VII), (Yousefi, Khalighi et al., 2008), [Hg(dmphen)I2], (VIII), (Yousefi, Rashidi Vahid et al., 2008), and {[HgCl(dm4bt)]2(µ-Cl)2}, (IX), (Khavasi et al., 2008). [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bi- pyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate, en is ethylene- diamine, dmphen is 4,7-diphenyl-1,10-phenanthroline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. We have also reported the syntheses and crystal structures of iron(III) complexes of [Fe(bipy)Cl3(DMSO)], (X) and [Fe(phen)Cl3(DMSO)], (XI), (Amani et al., 2007) and [Fe(phen)Cl3(CH3OH)].CH3OH, (XII), (Khavasi et al., 2007) [where bipy is 2,2'-bipyridine, DMSO is dimethyl sulfoxide and phen is 1,10-phenanthroline]. There are several InIII complexes, with formula, [In(N—N)Cl3(L)], (L = DMSO, H2O and EtOH), such as [In(bipy)Cl3(H2O)], (XIII), [In(bipy)Cl3(EtOH)], (XIV) and [In(bipy)Cl3(H2O)].H2O, (XV), (Malyarick et al., 1992), [In(phen)Cl3(DMSO)], (XVI), (Nan et al., 1987), [In(4,4'-dmbpy)Cl3(DMSO)],(XVII), (Ahmadi, Kalateh, Abedi et al., 2008), [In(phen)Cl3(H2O)], (XVIII), and [In(phen)Cl3(EtOH)].EtOH, (XIX), (Ilyukhin & Malyarick, 1994) have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (Fig. 1), the InIII atom is six-coordinated in a distorted octahedral configuration by two N atoms from the chelating 5,5'-dimethyl-2,2'-bipyridine ligand, one O atom from one methanol and three Cl atoms. The In—Cl and In—N bond lengths and angles (Table 1) are within normal ranges, as in (XIII), (XIV), (XV) and (XVII).

In the crystal structure, intermolecular O—H···Cl hydrogen bonds (Table 2) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

For the preparation of the title compound, (I), a solution of 5,5'-dimethyl -2,2'-bipyridine (0.20 g, 1.10 mmol) in methanol (20 ml) was added to a solution of InCl3.4H2O (0.16 g, 0.55 mmol) in methanol (50 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.18 g, 74.8%, m.p. <573 K).

Refinement top

H1B atom (for OH) was located in difference synthesis and refined isotropically [O-H = 0.83 (5) Å; Uiso(H) = 0.036 (11) Å2]. The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
Trichlorido(5,5'-dimethyl-2,2'-bipyridine- κ2N,N')(methanol-κO)indium(III) top
Crystal data top
[InCl3(C12H12N2)(CH4O)]F(000) = 864
Mr = 437.45Dx = 1.862 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1324 reflections
a = 10.9080 (6) Åθ = 2.0–29.2°
b = 11.2087 (7) ŵ = 2.02 mm−1
c = 13.3584 (8) ÅT = 120 K
β = 107.211 (4)°Block, colorless
V = 1560.12 (16) Å30.17 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		4185 independent reflections
Radiation source: fine-focus sealed tube3716 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 29.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		h = −14→14
Tmin = 0.729, Tmax = 0.820k = −15→15
12144 measured reflectionsl = −14→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H 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 parametersΔρmax = 0.92 e Å−3
0 restraintsΔρmin = −0.68 e Å−3
Crystal data top
[InCl3(C12H12N2)(CH4O)]V = 1560.12 (16) Å3
Mr = 437.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.9080 (6) ŵ = 2.02 mm−1
b = 11.2087 (7) ÅT = 120 K
c = 13.3584 (8) Å0.17 × 0.15 × 0.10 mm
β = 107.211 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4185 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		3716 reflections with I > 2σ(I)
Tmin = 0.729, Tmax = 0.820Rint = 0.043
12144 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.92 e Å−3
4185 reflectionsΔρmin = −0.68 e Å−3
185 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
xyzUiso*/Ueq
In10.773908 (15)0.320581 (14)−0.004168 (13)0.01003 (5)
Cl10.87230 (6)0.29569 (5)−0.14993 (5)0.01500 (11)
Cl20.55271 (5)0.31788 (6)−0.11430 (5)0.01766 (12)
Cl30.79945 (6)0.53204 (5)0.02679 (5)0.01588 (11)
O10.69912 (19)0.30834 (17)0.13936 (16)0.0178 (4)
H1B0.740 (4)0.280 (4)0.197 (4)0.036 (11)*
N10.7811 (2)0.11891 (18)0.01880 (17)0.0126 (4)
N20.97004 (19)0.27552 (18)0.10949 (16)0.0109 (4)
C10.6867 (2)0.0450 (2)−0.0335 (2)0.0152 (5)
H10.60980.0782−0.07400.018*
C20.6982 (3)−0.0788 (2)−0.0299 (2)0.0160 (5)
C30.5882 (3)−0.1568 (2)−0.0885 (2)0.0222 (5)
H3A0.5655−0.1386−0.16190.027*
H3B0.5158−0.1426−0.06320.027*
H3C0.6132−0.2391−0.07770.027*
C40.8152 (3)−0.1254 (2)0.0288 (2)0.0172 (5)
H40.8282−0.20750.03100.021*
C50.9129 (2)−0.0502 (2)0.0843 (2)0.0161 (5)
H50.9908−0.08150.12470.019*
C60.8929 (2)0.0732 (2)0.07869 (19)0.0123 (4)
C70.9932 (2)0.1588 (2)0.13432 (19)0.0117 (4)
C81.1071 (2)0.1235 (2)0.2067 (2)0.0154 (5)
H81.12020.04400.22690.018*
C91.2017 (2)0.2081 (2)0.2486 (2)0.0151 (5)
H91.27820.18520.29740.018*
C101.1821 (2)0.3271 (2)0.21787 (19)0.0136 (4)
C111.2857 (2)0.4191 (2)0.2546 (2)0.0171 (5)
H11A1.25650.48120.29140.020*
H11B1.30600.45250.19520.020*
H11C1.36100.38240.30060.020*
C121.0617 (2)0.3568 (2)0.15016 (19)0.0137 (4)
H121.04420.43650.13240.016*
C130.6145 (3)0.3950 (2)0.1646 (2)0.0186 (5)
H13A0.53590.39910.10830.022*
H13B0.65520.47180.17440.022*
H13C0.59630.37150.22780.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
In10.00974 (8)0.00875 (8)0.00997 (8)0.00064 (6)0.00040 (5)0.00051 (6)
Cl10.0161 (3)0.0161 (3)0.0129 (3)0.0011 (2)0.0044 (2)−0.0003 (2)
Cl20.0119 (2)0.0182 (3)0.0186 (3)0.0012 (2)−0.0019 (2)0.0003 (2)
Cl30.0203 (3)0.0100 (2)0.0166 (3)−0.0002 (2)0.0043 (2)−0.0008 (2)
O10.0205 (9)0.0188 (9)0.0152 (9)0.0059 (7)0.0071 (7)0.0035 (7)
N10.0118 (9)0.0110 (9)0.0136 (10)−0.0003 (7)0.0015 (8)0.0011 (7)
N20.0111 (9)0.0103 (8)0.0102 (9)−0.0003 (7)0.0017 (7)0.0009 (7)
C10.0161 (11)0.0140 (11)0.0152 (12)−0.0024 (9)0.0038 (9)−0.0015 (9)
C20.0211 (12)0.0132 (11)0.0154 (11)−0.0040 (9)0.0080 (10)−0.0008 (9)
C30.0250 (13)0.0181 (12)0.0230 (14)−0.0078 (10)0.0062 (11)−0.0056 (10)
C40.0246 (13)0.0096 (10)0.0204 (13)−0.0005 (9)0.0112 (10)0.0004 (9)
C50.0177 (11)0.0128 (10)0.0181 (12)0.0048 (9)0.0059 (10)0.0038 (9)
C60.0125 (11)0.0128 (10)0.0116 (11)0.0017 (8)0.0035 (9)0.0016 (8)
C70.0124 (10)0.0124 (10)0.0106 (10)0.0012 (8)0.0037 (8)0.0019 (8)
C80.0147 (11)0.0136 (11)0.0166 (12)0.0030 (9)0.0025 (9)0.0033 (9)
C90.0119 (10)0.0189 (11)0.0127 (11)0.0020 (9)0.0006 (9)0.0022 (9)
C100.0131 (10)0.0164 (11)0.0111 (10)−0.0009 (9)0.0033 (8)−0.0015 (9)
C110.0124 (11)0.0211 (12)0.0149 (12)−0.0022 (9)−0.0004 (9)0.0005 (10)
C120.0139 (11)0.0150 (10)0.0117 (11)0.0010 (8)0.0030 (9)0.0023 (9)
C130.0183 (12)0.0173 (11)0.0227 (13)0.0012 (9)0.0098 (10)−0.0030 (10)
Geometric parameters (Å, º) top
In1—Cl12.5015 (6)C6—N11.347 (3)
In1—Cl22.4262 (6)C6—C71.479 (3)
In1—Cl32.4080 (6)C7—N21.355 (3)
In1—O12.2991 (19)C7—C81.387 (3)
In1—N12.279 (2)C8—C91.391 (4)
In1—N22.284 (2)C8—H80.9300
O1—H1B0.83 (5)C9—C101.394 (4)
C1—N11.345 (3)C9—H90.9300
C1—C21.393 (3)C10—C121.397 (3)
C1—H10.9300C10—C111.501 (3)
C2—C41.387 (4)C11—H11A0.9600
C2—C31.504 (4)C11—H11B0.9600
C3—H3A0.9600C11—H11C0.9600
C3—H3B0.9600C12—N21.343 (3)
C3—H3C0.9600C12—H120.9300
C4—C51.389 (4)C13—O11.447 (3)
C4—H40.9300C13—H13A0.9600
C5—C61.399 (3)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
Cl2—In1—Cl196.05 (2)C2—C4—C5120.4 (2)
Cl3—In1—Cl1100.89 (2)C2—C4—H4119.8
Cl3—In1—Cl299.22 (2)C5—C4—H4119.8
O1—In1—Cl1169.20 (5)C4—C5—C6119.2 (2)
O1—In1—Cl288.30 (5)C4—C5—H5120.4
O1—In1—Cl388.11 (5)C6—C5—H5120.4
N1—In1—Cl189.35 (5)N1—C6—C5120.5 (2)
N1—In1—Cl293.30 (5)N1—C6—C7117.2 (2)
N1—In1—Cl3162.82 (6)C5—C6—C7122.3 (2)
N1—In1—O180.51 (7)N2—C7—C8120.6 (2)
N1—In1—N272.73 (7)N2—C7—C6116.6 (2)
N2—In1—Cl187.68 (5)C8—C7—C6122.8 (2)
N2—In1—Cl2165.54 (5)C7—C8—C9119.4 (2)
N2—In1—Cl393.76 (5)C7—C8—H8120.3
N2—In1—O185.77 (7)C9—C8—H8120.3
In1—O1—H1B125 (3)C8—C9—C10120.2 (2)
C13—O1—In1124.22 (16)C8—C9—H9119.9
C13—O1—H1B104 (3)C10—C9—H9119.9
C1—N1—In1123.41 (17)C9—C10—C12116.8 (2)
C1—N1—C6119.6 (2)C9—C10—C11121.8 (2)
C6—N1—In1116.52 (16)C12—C10—C11121.4 (2)
C7—N2—In1116.51 (16)C10—C11—H11A109.5
C12—N2—In1123.91 (16)C10—C11—H11B109.5
C12—N2—C7119.6 (2)H11A—C11—H11B109.5
N1—C1—C2123.3 (3)C10—C11—H11C109.5
N1—C1—H1118.4H11A—C11—H11C109.5
C2—C1—H1118.4H11B—C11—H11C109.5
C4—C2—C1116.9 (2)N2—C12—C10123.1 (2)
C4—C2—C3122.3 (2)N2—C12—H12118.5
C1—C2—C3120.8 (3)C10—C12—H12118.5
C2—C3—H3A109.5O1—C13—H13A109.5
C2—C3—H3B109.5O1—C13—H13B109.5
H3A—C3—H3B109.5H13A—C13—H13B109.5
C2—C3—H3C109.5O1—C13—H13C109.5
H3A—C3—H3C109.5H13A—C13—H13C109.5
H3B—C3—H3C109.5H13B—C13—H13C109.5
N1—In1—O1—C13−152.9 (2)N1—C1—C2—C3178.8 (2)
N2—In1—O1—C13133.9 (2)C1—C2—C4—C52.5 (4)
Cl3—In1—O1—C1340.01 (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—C195.6 (2)C5—C6—N1—C12.0 (4)
Cl3—In1—N1—C1144.79 (17)C7—C6—N1—C1−180.0 (2)
Cl2—In1—N1—C17.9 (2)C5—C6—N1—In1−170.21 (19)
Cl1—In1—N1—C1−88.11 (19)C7—C6—N1—In17.8 (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—N2169.6 (2)
Cl3—In1—N1—C6−43.3 (3)N1—C6—C7—C8173.2 (2)
Cl2—In1—N1—C6179.80 (17)C5—C6—C7—C8−8.9 (4)
Cl1—In1—N1—C683.78 (17)C8—C7—N2—C124.4 (4)
N1—In1—N2—C12178.2 (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—In14.6 (3)
Cl2—In1—N2—C12−166.46 (16)N2—C7—C8—C9−4.3 (4)
Cl1—In1—N2—C1288.17 (19)C6—C7—C8—C9174.2 (2)
N1—In1—N2—C7−0.55 (16)C7—C8—C9—C10−0.2 (4)
O1—In1—N2—C780.81 (17)C8—C9—C10—C124.4 (4)
Cl3—In1—N2—C7168.64 (17)C8—C9—C10—C11−174.9 (2)
Cl2—In1—N2—C714.8 (3)C9—C10—C12—N2−4.5 (4)
Cl1—In1—N2—C7−90.59 (17)C11—C10—C12—N2174.9 (2)
C2—C1—N1—C6−0.5 (4)C10—C12—N2—C70.1 (4)
C2—C1—N1—In1171.1 (2)C10—C12—N2—In1−178.61 (18)
N1—C1—C2—C4−1.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···Cl1i0.83 (5)2.29 (5)3.115 (2)174 (4)
Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[InCl3(C12H12N2)(CH4O)]
Mr437.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)10.9080 (6), 11.2087 (7), 13.3584 (8)
β (°) 107.211 (4)
V (Å3)1560.12 (16)
Z4
Radiation typeMo Kα
µ (mm−1)2.02
Crystal size (mm)0.17 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.729, 0.820
No. of measured, independent and
observed [I > 2σ(I)] reflections		12144, 4185, 3716
Rint0.043
(sin θ/λ)max (Å−1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.062, 1.15
No. of reflections4185
No. of parameters185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.92, −0.68

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
In1—Cl12.5015 (6)In1—O12.2991 (19)
In1—Cl22.4262 (6)In1—N12.279 (2)
In1—Cl32.4080 (6)In1—N22.284 (2)
Cl2—In1—Cl196.05 (2)N1—In1—Cl3162.82 (6)
Cl3—In1—Cl1100.89 (2)N1—In1—O180.51 (7)
Cl3—In1—Cl299.22 (2)N1—In1—N272.73 (7)
O1—In1—Cl1169.20 (5)N2—In1—Cl187.68 (5)
O1—In1—Cl288.30 (5)N2—In1—Cl2165.54 (5)
O1—In1—Cl388.11 (5)N2—In1—Cl393.76 (5)
N1—In1—Cl189.35 (5)N2—In1—O185.77 (7)
N1—In1—Cl293.30 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···Cl1i0.83 (5)2.29 (5)3.115 (2)174 (4)
Symmetry code: (i) x, −y+1/2, z+1/2.
 

Acknowledgements

The authors are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

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ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1353-m1354
doi:10.1107/S160053680803119X
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