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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1353–m1354.
Published online 2008 October 4. doi:  10.1107/S160053680803119X
PMCID: PMC2959790

Trichlorido(5,5′-dimethyl-2,2′-bipyridine-κ2 N,N′)(methanol-κO)indium(III)

Abstract

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

An external file that holds a picture, illustration, etc.
Object name is e-64-m1353-scheme1.jpg

Experimental

Crystal data

  • [InCl3(C12H12N2)(CH4O)]
  • M r = 437.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1353-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

[InCl3(C12H12N2)(CH4O)]F(000) = 864
Mr = 437.45Dx = 1.862 Mg m3
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 mm1
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

Bruker SMART CCD area-detector diffractometer4185 independent reflections
Radiation source: fine-focus sealed tube3716 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] 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

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 = 1.15w = 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 Å3
0 restraintsΔρmin = −0.68 e Å3

Special details

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)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
O1—H1B···Cl1i0.83 (5)2.29 (5)3.115 (2)174 (4)

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2541).

References

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