metal-organic compounds
Trichlorido(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)(dimethylformamide-κO)indium(III) hemihydrate
aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran, and bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
*Correspondence e-mail: sadif_shirvan1@yahoo.com
The 3(C12H12N2)(C3H7NO)]·0.5H2O, contains two independent InIII complex molecules with similar structures and one lattice water molecule. In each complex molecule, the InIII atom is six-coordinated in a distorted octahedral geometry, formed by two N atoms from the chelating 5,5′-dimethyl-2,2′-bipyridine ligand, one O atom from a dimethylformamide and three facial Cl atoms. In the crystal, the lattice water molecule is linked to the complex molecules via O—H⋯Cl hydrogen bonds. Further weak C—H⋯Cl and C—H⋯O hydrogen bonds result in the formation of a three-dimensional structure.
of the title compound, [InClRelated literature
For related structures, see: Albada et al. (2004); Alizadeh et al. (2010); Amani et al. (2007, 2009); Kalateh et al. (2008); Khalighi et al. (2008); Shirvan & Haydari Dezfuli (2012); Tadayon Pour et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812044698/xu5639sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044698/xu5639Isup2.hkl
For the preparation of the title compound, a solution of 5,5'-dimethyl-2,2'-bipyridine (0.30 g, 1.65 mmol) in methanol (10 ml) was added to a solution of InCl3.4H2O (0.48 g, 1.65 mmol) in methanol (10 ml) and the resulting colorless solution was stirred for 20 min at 323 K. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion to a colorless solution in dimethylformamide. Suitable crystals were isolated after one week (yield; 0.58 g, 72.1%).
Water H atoms were located in a difference Fourier map and refined with O—H distance of 0.84 (2) Å, Uiso(H) = 0.1 Å2. Other H atoms were positioned geometrically with C—H = 0.93 Å for aromatics H and 0.96 Å for methyl H atoms constrained to ride on their parent atoms, Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).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. Unit-cell packing diagram for title molecule. Hydrogen bonds are shown as dashed lines. |
[InCl3(C12H12N2)(C3H7NO)]·0.5H2O | Z = 4 |
Mr = 487.51 | F(000) = 972 |
Triclinic, P1 | Dx = 1.680 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3021 (5) Å | Cell parameters from 15402 reflections |
b = 11.4445 (5) Å | θ = 2.4–26.0° |
c = 15.0860 (6) Å | µ = 1.65 mm−1 |
α = 91.089 (4)° | T = 173 K |
β = 96.024 (3)° | Block, colorless |
γ = 96.448 (4)° | 0.32 × 0.30 × 0.25 mm |
V = 1927.34 (14) Å3 |
Bruker APEXII CCD area-detector diffractometer | 7524 independent reflections |
Radiation source: fine-focus sealed tube | 6051 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 26.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −13→13 |
Tmin = 0.601, Tmax = 0.688 | k = −14→14 |
15402 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0309P)2 + 0.5815P] where P = (Fo2 + 2Fc2)/3 |
7524 reflections | (Δ/σ)max = 0.001 |
437 parameters | Δρmax = 0.57 e Å−3 |
3 restraints | Δρmin = −0.54 e Å−3 |
[InCl3(C12H12N2)(C3H7NO)]·0.5H2O | γ = 96.448 (4)° |
Mr = 487.51 | V = 1927.34 (14) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.3021 (5) Å | Mo Kα radiation |
b = 11.4445 (5) Å | µ = 1.65 mm−1 |
c = 15.0860 (6) Å | T = 173 K |
α = 91.089 (4)° | 0.32 × 0.30 × 0.25 mm |
β = 96.024 (3)° |
Bruker APEXII CCD area-detector diffractometer | 7524 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6051 reflections with I > 2σ(I) |
Tmin = 0.601, Tmax = 0.688 | Rint = 0.036 |
15402 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.57 e Å−3 |
7524 reflections | Δρmin = −0.54 e Å−3 |
437 parameters |
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 | ||
C1 | 0.5123 (3) | 1.0246 (3) | 0.2042 (2) | 0.0251 (7) | |
H1 | 0.5450 | 1.0890 | 0.1746 | 0.030* | |
C2 | 0.3899 (3) | 1.0132 (3) | 0.2121 (2) | 0.0255 (7) | |
C3 | 0.3115 (3) | 1.1025 (4) | 0.1753 (3) | 0.0341 (9) | |
H3C | 0.2652 | 1.1270 | 0.2206 | 0.041* | |
H3B | 0.2587 | 1.0682 | 0.1253 | 0.041* | |
H3A | 0.3606 | 1.1694 | 0.1564 | 0.041* | |
C4 | 0.3441 (3) | 0.9152 (3) | 0.2551 (2) | 0.0277 (8) | |
H4 | 0.2625 | 0.9031 | 0.2608 | 0.033* | |
C5 | 0.4183 (3) | 0.8350 (3) | 0.2899 (2) | 0.0249 (7) | |
H5 | 0.3875 | 0.7697 | 0.3194 | 0.030* | |
C6 | 0.5403 (3) | 0.8539 (3) | 0.2797 (2) | 0.0222 (7) | |
C7 | 0.6250 (3) | 0.7694 (3) | 0.3113 (2) | 0.0206 (7) | |
C8 | 0.5969 (3) | 0.6830 (3) | 0.3715 (2) | 0.0261 (7) | |
H8 | 0.5227 | 0.6760 | 0.3935 | 0.031* | |
C9 | 0.6800 (3) | 0.6076 (3) | 0.3984 (2) | 0.0293 (8) | |
H9 | 0.6626 | 0.5510 | 0.4400 | 0.035* | |
C10 | 0.7899 (3) | 0.6162 (3) | 0.3633 (2) | 0.0272 (8) | |
C11 | 0.8797 (4) | 0.5334 (4) | 0.3906 (3) | 0.0377 (9) | |
H11C | 0.8845 | 0.5243 | 0.4539 | 0.045* | |
H11B | 0.9567 | 0.5645 | 0.3744 | 0.045* | |
H11A | 0.8554 | 0.4583 | 0.3609 | 0.045* | |
C12 | 0.8112 (3) | 0.7047 (3) | 0.3039 (2) | 0.0252 (7) | |
H12 | 0.8839 | 0.7117 | 0.2797 | 0.030* | |
C13 | 0.8628 (3) | 1.0800 (3) | 0.4086 (2) | 0.0269 (8) | |
H13 | 0.9023 | 1.1386 | 0.3770 | 0.032* | |
C14 | 0.9446 (4) | 1.1909 (4) | 0.5437 (3) | 0.0495 (12) | |
H14C | 1.0074 | 1.1657 | 0.5842 | 0.059* | |
H14B | 0.8924 | 1.2313 | 0.5766 | 0.059* | |
H14A | 0.9788 | 1.2430 | 0.5017 | 0.059* | |
C15 | 0.8199 (4) | 0.9974 (4) | 0.5493 (3) | 0.0422 (10) | |
H15A | 0.7973 | 0.9266 | 0.5134 | 0.051* | |
H15B | 0.7501 | 1.0237 | 0.5706 | 0.051* | |
H15C | 0.8756 | 0.9819 | 0.5990 | 0.051* | |
C16 | 0.4078 (3) | 0.2947 (3) | 0.3691 (2) | 0.0267 (7) | |
H16 | 0.3432 | 0.2736 | 0.4012 | 0.032* | |
C17 | 0.5101 (3) | 0.2392 (3) | 0.3877 (2) | 0.0272 (8) | |
C18 | 0.5177 (4) | 0.1442 (3) | 0.4548 (3) | 0.0359 (9) | |
H18A | 0.4572 | 0.0799 | 0.4372 | 0.043* | |
H18B | 0.5054 | 0.1751 | 0.5123 | 0.043* | |
H18C | 0.5953 | 0.1170 | 0.4577 | 0.043* | |
C19 | 0.6052 (3) | 0.2748 (3) | 0.3395 (2) | 0.0314 (8) | |
H19 | 0.6763 | 0.2410 | 0.3498 | 0.038* | |
C20 | 0.5954 (3) | 0.3597 (3) | 0.2764 (2) | 0.0312 (8) | |
H20 | 0.6594 | 0.3832 | 0.2442 | 0.037* | |
C21 | 0.4897 (3) | 0.4096 (3) | 0.2615 (2) | 0.0232 (7) | |
C22 | 0.4726 (3) | 0.5031 (3) | 0.1956 (2) | 0.0236 (7) | |
C23 | 0.5582 (3) | 0.5398 (3) | 0.1397 (2) | 0.0317 (8) | |
H23 | 0.6299 | 0.5067 | 0.1427 | 0.038* | |
C24 | 0.5356 (4) | 0.6265 (4) | 0.0791 (2) | 0.0341 (9) | |
H24 | 0.5925 | 0.6517 | 0.0411 | 0.041* | |
C25 | 0.4292 (3) | 0.6756 (3) | 0.0749 (2) | 0.0301 (8) | |
C26 | 0.4010 (4) | 0.7694 (4) | 0.0104 (3) | 0.0460 (11) | |
H26C | 0.4709 | 0.8250 | 0.0084 | 0.055* | |
H26B | 0.3371 | 0.8091 | 0.0293 | 0.055* | |
H26A | 0.3771 | 0.7341 | −0.0479 | 0.055* | |
C27 | 0.3478 (3) | 0.6325 (3) | 0.1325 (2) | 0.0287 (8) | |
H27 | 0.2744 | 0.6625 | 0.1295 | 0.034* | |
C28 | 0.1038 (3) | 0.2848 (4) | 0.1282 (2) | 0.0322 (8) | |
H28 | 0.0720 | 0.2356 | 0.1703 | 0.039* | |
C29 | 0.1028 (5) | 0.3466 (5) | −0.0221 (3) | 0.0639 (15) | |
H29C | 0.1406 | 0.3045 | −0.0648 | 0.077* | |
H29B | 0.1591 | 0.4090 | 0.0058 | 0.077* | |
H29A | 0.0352 | 0.3791 | −0.0518 | 0.077* | |
C30 | −0.0240 (5) | 0.1663 (6) | 0.0160 (3) | 0.0706 (18) | |
H30A | −0.0455 | 0.1230 | 0.0669 | 0.085* | |
H30B | 0.0105 | 0.1162 | −0.0235 | 0.085* | |
H30C | −0.0941 | 0.1933 | −0.0146 | 0.085* | |
N1 | 0.5854 (2) | 0.9478 (2) | 0.23712 (18) | 0.0219 (6) | |
N2 | 0.7329 (2) | 0.7812 (2) | 0.27921 (17) | 0.0209 (6) | |
N3 | 0.8759 (3) | 1.0879 (3) | 0.49582 (19) | 0.0290 (7) | |
N4 | 0.3964 (2) | 0.3764 (2) | 0.30794 (18) | 0.0229 (6) | |
N5 | 0.3691 (3) | 0.5500 (3) | 0.19222 (18) | 0.0234 (6) | |
N6 | 0.0629 (3) | 0.2669 (3) | 0.0452 (2) | 0.0378 (8) | |
O1 | 0.7993 (2) | 0.9967 (2) | 0.36637 (15) | 0.0309 (6) | |
O2 | 0.1854 (2) | 0.3663 (2) | 0.15434 (17) | 0.0375 (6) | |
O3 | 0.1661 (4) | 0.5577 (4) | −0.1491 (4) | 0.0903 (15) | |
Cl1 | 0.72933 (9) | 0.90119 (10) | 0.06210 (6) | 0.0395 (2) | |
Cl2 | 0.99623 (8) | 0.93947 (9) | 0.22712 (6) | 0.0333 (2) | |
Cl3 | 0.79761 (8) | 1.17277 (8) | 0.19951 (6) | 0.0313 (2) | |
Cl4 | 0.29650 (8) | 0.59312 (8) | 0.41650 (6) | 0.03024 (19) | |
Cl5 | 0.08798 (9) | 0.60500 (10) | 0.22539 (7) | 0.0435 (3) | |
Cl6 | 0.10673 (8) | 0.31911 (9) | 0.35452 (6) | 0.0355 (2) | |
In1 | 0.78415 (2) | 0.95952 (2) | 0.217222 (15) | 0.02104 (7) | |
In2 | 0.22743 (2) | 0.46926 (2) | 0.280738 (15) | 0.02290 (7) | |
H3D | 0.099 (2) | 0.521 (3) | −0.168 (3) | 0.100* | |
H3E | 0.155 (3) | 0.6286 (12) | −0.156 (3) | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0259 (18) | 0.0258 (18) | 0.0228 (16) | 0.0032 (14) | −0.0012 (14) | 0.0023 (14) |
C2 | 0.0253 (18) | 0.0315 (19) | 0.0194 (16) | 0.0047 (15) | −0.0001 (13) | −0.0012 (14) |
C3 | 0.029 (2) | 0.040 (2) | 0.034 (2) | 0.0100 (17) | 0.0012 (16) | 0.0072 (17) |
C4 | 0.0188 (17) | 0.037 (2) | 0.0276 (17) | 0.0032 (15) | 0.0036 (14) | −0.0021 (15) |
C5 | 0.0258 (18) | 0.0259 (18) | 0.0227 (16) | −0.0021 (14) | 0.0062 (14) | 0.0030 (14) |
C6 | 0.0249 (18) | 0.0227 (17) | 0.0184 (15) | −0.0008 (14) | 0.0042 (13) | −0.0016 (13) |
C7 | 0.0214 (17) | 0.0207 (17) | 0.0189 (15) | −0.0019 (13) | 0.0034 (13) | −0.0014 (13) |
C8 | 0.0228 (18) | 0.0287 (19) | 0.0278 (17) | 0.0010 (14) | 0.0087 (14) | 0.0035 (14) |
C9 | 0.034 (2) | 0.0283 (19) | 0.0262 (18) | 0.0044 (16) | 0.0052 (15) | 0.0079 (15) |
C10 | 0.0265 (19) | 0.0279 (19) | 0.0275 (17) | 0.0052 (15) | 0.0022 (14) | 0.0025 (14) |
C11 | 0.034 (2) | 0.039 (2) | 0.043 (2) | 0.0098 (18) | 0.0055 (18) | 0.0156 (18) |
C12 | 0.0220 (18) | 0.0290 (19) | 0.0244 (17) | 0.0020 (14) | 0.0032 (13) | −0.0009 (14) |
C13 | 0.0236 (18) | 0.033 (2) | 0.0238 (17) | 0.0024 (15) | 0.0026 (14) | 0.0021 (15) |
C14 | 0.059 (3) | 0.049 (3) | 0.034 (2) | −0.010 (2) | −0.003 (2) | −0.006 (2) |
C15 | 0.043 (2) | 0.059 (3) | 0.0232 (18) | −0.006 (2) | 0.0073 (17) | 0.0034 (18) |
C16 | 0.0285 (19) | 0.0246 (18) | 0.0280 (18) | 0.0033 (14) | 0.0071 (14) | 0.0036 (14) |
C17 | 0.031 (2) | 0.0233 (18) | 0.0261 (17) | 0.0031 (15) | −0.0029 (15) | −0.0003 (14) |
C18 | 0.040 (2) | 0.032 (2) | 0.037 (2) | 0.0107 (17) | 0.0023 (17) | 0.0090 (17) |
C19 | 0.031 (2) | 0.030 (2) | 0.035 (2) | 0.0141 (16) | 0.0039 (16) | 0.0006 (16) |
C20 | 0.0260 (19) | 0.033 (2) | 0.036 (2) | 0.0077 (16) | 0.0073 (16) | 0.0028 (16) |
C21 | 0.0237 (18) | 0.0223 (17) | 0.0227 (16) | 0.0005 (14) | 0.0006 (13) | 0.0013 (13) |
C22 | 0.0244 (18) | 0.0243 (18) | 0.0217 (16) | 0.0018 (14) | 0.0015 (13) | −0.0005 (13) |
C23 | 0.0263 (19) | 0.036 (2) | 0.0326 (19) | −0.0013 (16) | 0.0095 (15) | 0.0031 (16) |
C24 | 0.033 (2) | 0.042 (2) | 0.0265 (18) | −0.0049 (17) | 0.0088 (15) | 0.0060 (16) |
C25 | 0.032 (2) | 0.033 (2) | 0.0243 (18) | −0.0030 (16) | 0.0014 (15) | 0.0070 (15) |
C26 | 0.038 (2) | 0.058 (3) | 0.042 (2) | 0.003 (2) | 0.0017 (19) | 0.026 (2) |
C27 | 0.0258 (19) | 0.032 (2) | 0.0281 (18) | 0.0048 (15) | −0.0012 (15) | 0.0067 (15) |
C28 | 0.0259 (19) | 0.041 (2) | 0.0300 (19) | 0.0034 (17) | 0.0055 (15) | −0.0032 (16) |
C29 | 0.080 (4) | 0.075 (4) | 0.035 (2) | 0.016 (3) | −0.006 (2) | 0.007 (2) |
C30 | 0.045 (3) | 0.107 (5) | 0.053 (3) | −0.023 (3) | 0.013 (2) | −0.039 (3) |
N1 | 0.0232 (15) | 0.0209 (14) | 0.0210 (13) | 0.0001 (11) | 0.0022 (11) | 0.0026 (11) |
N2 | 0.0216 (14) | 0.0211 (14) | 0.0197 (13) | −0.0001 (11) | 0.0034 (11) | 0.0011 (11) |
N3 | 0.0267 (16) | 0.0348 (17) | 0.0238 (15) | −0.0005 (13) | −0.0006 (12) | −0.0027 (13) |
N4 | 0.0211 (15) | 0.0235 (15) | 0.0236 (14) | 0.0012 (12) | 0.0010 (11) | 0.0041 (11) |
N5 | 0.0220 (15) | 0.0279 (15) | 0.0197 (13) | 0.0001 (12) | 0.0015 (11) | 0.0029 (12) |
N6 | 0.0271 (17) | 0.055 (2) | 0.0313 (17) | 0.0066 (15) | 0.0014 (13) | −0.0081 (16) |
O1 | 0.0349 (15) | 0.0336 (14) | 0.0220 (12) | −0.0056 (11) | 0.0037 (10) | −0.0001 (11) |
O2 | 0.0383 (16) | 0.0420 (16) | 0.0289 (13) | −0.0062 (13) | 0.0002 (12) | −0.0016 (12) |
O3 | 0.066 (3) | 0.056 (2) | 0.153 (4) | 0.007 (2) | 0.023 (3) | 0.036 (3) |
Cl1 | 0.0392 (5) | 0.0567 (6) | 0.0198 (4) | −0.0049 (5) | 0.0021 (4) | −0.0024 (4) |
Cl2 | 0.0199 (4) | 0.0461 (6) | 0.0344 (5) | 0.0039 (4) | 0.0040 (3) | 0.0086 (4) |
Cl3 | 0.0316 (5) | 0.0272 (5) | 0.0364 (5) | 0.0020 (4) | 0.0097 (4) | 0.0079 (4) |
Cl4 | 0.0338 (5) | 0.0286 (5) | 0.0276 (4) | −0.0034 (4) | 0.0071 (4) | 0.0028 (3) |
Cl5 | 0.0327 (5) | 0.0588 (7) | 0.0450 (5) | 0.0229 (5) | 0.0101 (4) | 0.0232 (5) |
Cl6 | 0.0294 (5) | 0.0353 (5) | 0.0409 (5) | −0.0057 (4) | 0.0085 (4) | 0.0084 (4) |
In1 | 0.01898 (13) | 0.02579 (14) | 0.01822 (11) | 0.00006 (10) | 0.00357 (9) | 0.00353 (9) |
In2 | 0.01887 (13) | 0.02634 (14) | 0.02381 (13) | 0.00307 (10) | 0.00239 (9) | 0.00571 (10) |
C1—N1 | 1.340 (4) | C18—H18C | 0.9600 |
C1—C2 | 1.393 (5) | C19—C20 | 1.378 (5) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C4 | 1.383 (5) | C20—C21 | 1.381 (5) |
C2—C3 | 1.504 (5) | C20—H20 | 0.9300 |
C3—H3C | 0.9600 | C21—N4 | 1.349 (4) |
C3—H3B | 0.9600 | C21—C22 | 1.490 (5) |
C3—H3A | 0.9600 | C22—N5 | 1.337 (4) |
C4—C5 | 1.386 (5) | C22—C23 | 1.385 (5) |
C4—H4 | 0.9300 | C23—C24 | 1.389 (6) |
C5—C6 | 1.396 (5) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.380 (6) |
C6—N1 | 1.342 (4) | C24—H24 | 0.9300 |
C6—C7 | 1.487 (5) | C25—C27 | 1.387 (5) |
C7—N2 | 1.352 (4) | C25—C26 | 1.501 (5) |
C7—C8 | 1.388 (5) | C26—H26C | 0.9600 |
C8—C9 | 1.381 (5) | C26—H26B | 0.9600 |
C8—H8 | 0.9300 | C26—H26A | 0.9600 |
C9—C10 | 1.395 (5) | C27—N5 | 1.341 (4) |
C9—H9 | 0.9300 | C27—H27 | 0.9300 |
C10—C12 | 1.384 (5) | C28—O2 | 1.262 (4) |
C10—C11 | 1.496 (5) | C28—N6 | 1.293 (5) |
C11—H11C | 0.9600 | C28—H28 | 0.9300 |
C11—H11B | 0.9600 | C29—N6 | 1.452 (6) |
C11—H11A | 0.9600 | C29—H29C | 0.9600 |
C12—N2 | 1.343 (4) | C29—H29B | 0.9600 |
C12—H12 | 0.9300 | C29—H29A | 0.9600 |
C13—O1 | 1.248 (4) | C30—N6 | 1.456 (6) |
C13—N3 | 1.309 (4) | C30—H30A | 0.9600 |
C13—H13 | 0.9300 | C30—H30B | 0.9600 |
C14—N3 | 1.469 (5) | C30—H30C | 0.9600 |
C14—H14C | 0.9600 | O3—H3D | 0.844 (10) |
C14—H14B | 0.9600 | O3—H3E | 0.841 (10) |
C14—H14A | 0.9600 | In1—Cl1 | 2.4185 (9) |
C15—N3 | 1.454 (5) | In1—Cl2 | 2.4227 (9) |
C15—H15A | 0.9600 | In1—Cl3 | 2.4496 (9) |
C15—H15B | 0.9600 | In1—O1 | 2.267 (2) |
C15—H15C | 0.9600 | In1—N1 | 2.287 (3) |
C16—N4 | 1.333 (4) | In1—N2 | 2.301 (3) |
C16—C17 | 1.387 (5) | In2—Cl4 | 2.4737 (9) |
C16—H16 | 0.9300 | In2—Cl5 | 2.4327 (10) |
C17—C19 | 1.388 (5) | In2—Cl6 | 2.4326 (9) |
C17—C18 | 1.502 (5) | In2—O2 | 2.202 (3) |
C18—H18A | 0.9600 | In2—N4 | 2.292 (3) |
C18—H18B | 0.9600 | In2—N5 | 2.316 (3) |
N1—C1—C2 | 123.4 (3) | C24—C23—H23 | 120.4 |
N1—C1—H1 | 118.3 | C25—C24—C23 | 120.2 (3) |
C2—C1—H1 | 118.3 | C25—C24—H24 | 119.9 |
C4—C2—C1 | 116.6 (3) | C23—C24—H24 | 119.9 |
C4—C2—C3 | 121.7 (3) | C24—C25—C27 | 116.7 (3) |
C1—C2—C3 | 121.6 (3) | C24—C25—C26 | 122.0 (3) |
C2—C3—H3C | 109.5 | C27—C25—C26 | 121.3 (4) |
C2—C3—H3B | 109.5 | C25—C26—H26C | 109.5 |
H3C—C3—H3B | 109.5 | C25—C26—H26B | 109.5 |
C2—C3—H3A | 109.5 | H26C—C26—H26B | 109.5 |
H3C—C3—H3A | 109.5 | C25—C26—H26A | 109.5 |
H3B—C3—H3A | 109.5 | H26C—C26—H26A | 109.5 |
C2—C4—C5 | 120.8 (3) | H26B—C26—H26A | 109.5 |
C2—C4—H4 | 119.6 | N5—C27—C25 | 123.7 (3) |
C5—C4—H4 | 119.6 | N5—C27—H27 | 118.2 |
C4—C5—C6 | 118.8 (3) | C25—C27—H27 | 118.2 |
C4—C5—H5 | 120.6 | O2—C28—N6 | 122.5 (4) |
C6—C5—H5 | 120.6 | O2—C28—H28 | 118.7 |
N1—C6—C5 | 120.9 (3) | N6—C28—H28 | 118.7 |
N1—C6—C7 | 116.8 (3) | N6—C29—H29C | 109.5 |
C5—C6—C7 | 122.2 (3) | N6—C29—H29B | 109.5 |
N2—C7—C8 | 120.9 (3) | H29C—C29—H29B | 109.5 |
N2—C7—C6 | 116.7 (3) | N6—C29—H29A | 109.5 |
C8—C7—C6 | 122.4 (3) | H29C—C29—H29A | 109.5 |
C9—C8—C7 | 119.5 (3) | H29B—C29—H29A | 109.5 |
C9—C8—H8 | 120.3 | N6—C30—H30A | 109.5 |
C7—C8—H8 | 120.3 | N6—C30—H30B | 109.5 |
C8—C9—C10 | 120.1 (3) | H30A—C30—H30B | 109.5 |
C8—C9—H9 | 119.9 | N6—C30—H30C | 109.5 |
C10—C9—H9 | 119.9 | H30A—C30—H30C | 109.5 |
C12—C10—C9 | 116.8 (3) | H30B—C30—H30C | 109.5 |
C12—C10—C11 | 122.6 (3) | C1—N1—C6 | 119.4 (3) |
C9—C10—C11 | 120.6 (3) | C1—N1—In1 | 123.7 (2) |
C10—C11—H11C | 109.5 | C6—N1—In1 | 116.7 (2) |
C10—C11—H11B | 109.5 | C12—N2—C7 | 118.8 (3) |
H11C—C11—H11B | 109.5 | C12—N2—In1 | 124.1 (2) |
C10—C11—H11A | 109.5 | C7—N2—In1 | 115.0 (2) |
H11C—C11—H11A | 109.5 | C13—N3—C15 | 121.6 (3) |
H11B—C11—H11A | 109.5 | C13—N3—C14 | 121.2 (3) |
N2—C12—C10 | 123.8 (3) | C15—N3—C14 | 117.2 (3) |
N2—C12—H12 | 118.1 | C16—N4—C21 | 119.0 (3) |
C10—C12—H12 | 118.1 | C16—N4—In2 | 123.1 (2) |
O1—C13—N3 | 122.3 (3) | C21—N4—In2 | 117.8 (2) |
O1—C13—H13 | 118.8 | C22—N5—C27 | 119.1 (3) |
N3—C13—H13 | 118.8 | C22—N5—In2 | 117.4 (2) |
N3—C14—H14C | 109.5 | C27—N5—In2 | 123.2 (2) |
N3—C14—H14B | 109.5 | C28—N6—C29 | 120.8 (4) |
H14C—C14—H14B | 109.5 | C28—N6—C30 | 121.4 (4) |
N3—C14—H14A | 109.5 | C29—N6—C30 | 117.8 (4) |
H14C—C14—H14A | 109.5 | C13—O1—In1 | 126.5 (2) |
H14B—C14—H14A | 109.5 | C28—O2—In2 | 132.3 (3) |
N3—C15—H15A | 109.5 | H3D—O3—H3E | 103.2 (16) |
N3—C15—H15B | 109.5 | O1—In1—N1 | 80.31 (9) |
H15A—C15—H15B | 109.5 | O1—In1—N2 | 74.40 (9) |
N3—C15—H15C | 109.5 | N1—In1—N2 | 72.49 (10) |
H15A—C15—H15C | 109.5 | O1—In1—Cl1 | 168.73 (7) |
H15B—C15—H15C | 109.5 | N1—In1—Cl1 | 89.31 (7) |
N4—C16—C17 | 124.0 (3) | N2—In1—Cl1 | 98.40 (7) |
N4—C16—H16 | 118.0 | O1—In1—Cl2 | 90.23 (7) |
C17—C16—H16 | 118.0 | N1—In1—Cl2 | 165.72 (7) |
C16—C17—C19 | 116.1 (3) | N2—In1—Cl2 | 94.75 (7) |
C16—C17—C18 | 122.3 (3) | Cl1—In1—Cl2 | 99.11 (3) |
C19—C17—C18 | 121.5 (3) | O1—In1—Cl3 | 87.14 (7) |
C17—C18—H18A | 109.5 | N1—In1—Cl3 | 92.18 (7) |
C17—C18—H18B | 109.5 | N2—In1—Cl3 | 157.55 (7) |
H18A—C18—H18B | 109.5 | Cl1—In1—Cl3 | 97.68 (4) |
C17—C18—H18C | 109.5 | Cl2—In1—Cl3 | 98.06 (3) |
H18A—C18—H18C | 109.5 | O2—In2—N4 | 88.49 (10) |
H18B—C18—H18C | 109.5 | O2—In2—N5 | 76.22 (10) |
C20—C19—C17 | 120.7 (3) | N4—In2—N5 | 71.49 (10) |
C20—C19—H19 | 119.6 | O2—In2—Cl6 | 89.75 (7) |
C17—C19—H19 | 119.6 | N4—In2—Cl6 | 92.52 (7) |
C19—C20—C21 | 119.3 (4) | N5—In2—Cl6 | 158.71 (8) |
C19—C20—H20 | 120.4 | O2—In2—Cl5 | 89.31 (8) |
C21—C20—H20 | 120.4 | N4—In2—Cl5 | 162.54 (7) |
N4—C21—C20 | 120.9 (3) | N5—In2—Cl5 | 91.17 (8) |
N4—C21—C22 | 116.6 (3) | Cl6—In2—Cl5 | 104.79 (4) |
C20—C21—C22 | 122.6 (3) | O2—In2—Cl4 | 173.50 (8) |
N5—C22—C23 | 121.1 (3) | N4—In2—Cl4 | 87.98 (7) |
N5—C22—C21 | 116.6 (3) | N5—In2—Cl4 | 97.47 (7) |
C23—C22—C21 | 122.3 (3) | Cl6—In2—Cl4 | 95.86 (3) |
C22—C23—C24 | 119.2 (4) | Cl5—In2—Cl4 | 92.42 (4) |
C22—C23—H23 | 120.4 | ||
N1—C1—C2—C4 | −1.2 (5) | C23—C22—N5—In2 | 174.8 (3) |
N1—C1—C2—C3 | 179.1 (3) | C21—C22—N5—In2 | −4.7 (4) |
C1—C2—C4—C5 | 1.4 (5) | C25—C27—N5—C22 | −2.1 (5) |
C3—C2—C4—C5 | −178.9 (3) | C25—C27—N5—In2 | −175.4 (3) |
C2—C4—C5—C6 | −0.8 (5) | O2—C28—N6—C29 | −4.9 (6) |
C4—C5—C6—N1 | −0.1 (5) | O2—C28—N6—C30 | 174.8 (4) |
C4—C5—C6—C7 | −177.1 (3) | N3—C13—O1—In1 | −172.6 (3) |
N1—C6—C7—N2 | −12.9 (4) | N6—C28—O2—In2 | 151.2 (3) |
C5—C6—C7—N2 | 164.3 (3) | C13—O1—In1—N1 | −130.2 (3) |
N1—C6—C7—C8 | 166.3 (3) | C13—O1—In1—N2 | 155.4 (3) |
C5—C6—C7—C8 | −16.5 (5) | C13—O1—In1—Cl1 | −153.3 (3) |
N2—C7—C8—C9 | −0.5 (5) | C13—O1—In1—Cl2 | 60.6 (3) |
C6—C7—C8—C9 | −179.7 (3) | C13—O1—In1—Cl3 | −37.5 (3) |
C7—C8—C9—C10 | −1.8 (5) | C1—N1—In1—O1 | 113.0 (3) |
C8—C9—C10—C12 | 2.0 (5) | C6—N1—In1—O1 | −71.1 (2) |
C8—C9—C10—C11 | −178.8 (3) | C1—N1—In1—N2 | −170.4 (3) |
C9—C10—C12—N2 | 0.2 (5) | C6—N1—In1—N2 | 5.5 (2) |
C11—C10—C12—N2 | −179.1 (3) | C1—N1—In1—Cl1 | −71.4 (2) |
N4—C16—C17—C19 | 1.2 (5) | C6—N1—In1—Cl1 | 104.5 (2) |
N4—C16—C17—C18 | −177.6 (3) | C1—N1—In1—Cl2 | 162.2 (2) |
C16—C17—C19—C20 | −0.7 (5) | C6—N1—In1—Cl2 | −22.0 (5) |
C18—C17—C19—C20 | 178.2 (3) | C1—N1—In1—Cl3 | 26.3 (2) |
C17—C19—C20—C21 | 0.1 (6) | C6—N1—In1—Cl3 | −157.8 (2) |
C19—C20—C21—N4 | 0.1 (5) | C12—N2—In1—O1 | −91.2 (3) |
C19—C20—C21—C22 | 179.1 (3) | C7—N2—In1—O1 | 72.3 (2) |
N4—C21—C22—N5 | 3.7 (4) | C12—N2—In1—N1 | −175.7 (3) |
C20—C21—C22—N5 | −175.3 (3) | C7—N2—In1—N1 | −12.3 (2) |
N4—C21—C22—C23 | −175.8 (3) | C12—N2—In1—Cl1 | 97.7 (2) |
C20—C21—C22—C23 | 5.2 (5) | C7—N2—In1—Cl1 | −98.9 (2) |
N5—C22—C23—C24 | −0.2 (5) | C12—N2—In1—Cl2 | −2.2 (2) |
C21—C22—C23—C24 | 179.3 (3) | C7—N2—In1—Cl2 | 161.2 (2) |
C22—C23—C24—C25 | 0.1 (6) | C12—N2—In1—Cl3 | −126.9 (2) |
C23—C24—C25—C27 | −1.0 (5) | C7—N2—In1—Cl3 | 36.5 (3) |
C23—C24—C25—C26 | −179.9 (4) | C28—O2—In2—N4 | 111.2 (4) |
C24—C25—C27—N5 | 2.1 (5) | C28—O2—In2—N5 | −177.5 (4) |
C26—C25—C27—N5 | −179.1 (4) | C28—O2—In2—Cl6 | 18.7 (4) |
C2—C1—N1—C6 | 0.4 (5) | C28—O2—In2—Cl5 | −86.1 (4) |
C2—C1—N1—In1 | 176.1 (2) | C28—O2—In2—Cl4 | 168.4 (5) |
C5—C6—N1—C1 | 0.3 (5) | C16—N4—In2—O2 | −107.4 (3) |
C7—C6—N1—C1 | 177.5 (3) | C21—N4—In2—O2 | 74.9 (2) |
C5—C6—N1—In1 | −175.7 (2) | C16—N4—In2—N5 | 176.6 (3) |
C7—C6—N1—In1 | 1.4 (3) | C21—N4—In2—N5 | −1.0 (2) |
C10—C12—N2—C7 | −2.5 (5) | C16—N4—In2—Cl6 | −17.7 (3) |
C10—C12—N2—In1 | 160.4 (3) | C21—N4—In2—Cl6 | 164.6 (2) |
C8—C7—N2—C12 | 2.6 (5) | C16—N4—In2—Cl5 | 169.7 (2) |
C6—C7—N2—C12 | −178.2 (3) | C21—N4—In2—Cl5 | −8.0 (4) |
C8—C7—N2—In1 | −161.8 (2) | C16—N4—In2—Cl4 | 78.1 (3) |
C6—C7—N2—In1 | 17.5 (3) | C21—N4—In2—Cl4 | −99.6 (2) |
O1—C13—N3—C15 | 2.1 (6) | C22—N5—In2—O2 | −89.9 (2) |
O1—C13—N3—C14 | −175.8 (4) | C27—N5—In2—O2 | 83.5 (3) |
C17—C16—N4—C21 | −1.1 (5) | C22—N5—In2—N4 | 3.1 (2) |
C17—C16—N4—In2 | −178.7 (3) | C27—N5—In2—N4 | 176.5 (3) |
C20—C21—N4—C16 | 0.4 (5) | C22—N5—In2—Cl6 | −39.9 (4) |
C22—C21—N4—C16 | −178.7 (3) | C27—N5—In2—Cl6 | 133.5 (2) |
C20—C21—N4—In2 | 178.1 (3) | C22—N5—In2—Cl5 | −178.9 (2) |
C22—C21—N4—In2 | −0.9 (4) | C27—N5—In2—Cl5 | −5.5 (3) |
C23—C22—N5—C27 | 1.1 (5) | C22—N5—In2—Cl4 | 88.5 (2) |
C21—C22—N5—C27 | −178.4 (3) | C27—N5—In2—Cl4 | −98.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3D···Cl5i | 0.84 (3) | 2.49 (3) | 3.326 (5) | 174 (3) |
O3—H3E···Cl3ii | 0.84 (2) | 2.40 (2) | 3.183 (5) | 156 (3) |
C5—H5···Cl4 | 0.93 | 2.69 | 3.620 (3) | 175 |
C8—H8···Cl4 | 0.93 | 2.69 | 3.574 (4) | 160 |
C9—H9···Cl4iii | 0.93 | 2.78 | 3.657 (3) | 158 |
C16—H16···Cl6 | 0.93 | 2.80 | 3.430 (4) | 126 |
C20—H20···O3iv | 0.93 | 2.60 | 3.526 (6) | 178 |
C23—H23···O3iv | 0.93 | 2.49 | 3.416 (6) | 173 |
C27—H27···Cl5 | 0.93 | 2.71 | 3.370 (4) | 129 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [InCl3(C12H12N2)(C3H7NO)]·0.5H2O |
Mr | 487.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 11.3021 (5), 11.4445 (5), 15.0860 (6) |
α, β, γ (°) | 91.089 (4), 96.024 (3), 96.448 (4) |
V (Å3) | 1927.34 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.65 |
Crystal size (mm) | 0.32 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.601, 0.688 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15402, 7524, 6051 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.067, 1.03 |
No. of reflections | 7524 |
No. of parameters | 437 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.54 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
In1—Cl1 | 2.4185 (9) | In2—Cl4 | 2.4737 (9) |
In1—Cl2 | 2.4227 (9) | In2—Cl5 | 2.4327 (10) |
In1—Cl3 | 2.4496 (9) | In2—Cl6 | 2.4326 (9) |
In1—O1 | 2.267 (2) | In2—O2 | 2.202 (3) |
In1—N1 | 2.287 (3) | In2—N4 | 2.292 (3) |
In1—N2 | 2.301 (3) | In2—N5 | 2.316 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3D···Cl5i | 0.84 (3) | 2.49 (3) | 3.326 (5) | 174 (3) |
O3—H3E···Cl3ii | 0.842 (17) | 2.396 (19) | 3.183 (5) | 156 (3) |
C5—H5···Cl4 | 0.93 | 2.69 | 3.620 (3) | 175 |
C8—H8···Cl4 | 0.93 | 2.69 | 3.574 (4) | 160 |
C9—H9···Cl4iii | 0.93 | 2.78 | 3.657 (3) | 158 |
C20—H20···O3iv | 0.93 | 2.60 | 3.526 (6) | 178 |
C23—H23···O3iv | 0.93 | 2.49 | 3.416 (6) | 173 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z. |
Acknowledgements
We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Recently, we reported the synthes and crystal structure of [Cd(5,5'-dmbpy)(µ-Br)2]n, (Shirvan & Haydari Dezfuli, 2012) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine]. 5,5'-Dimethyl-2,2'-bipyridine is a good bidentate ligand, and numerous complexes with 5,5'-dmbipy have been prepared, such as that of zinc (Khalighi et al., 2008), indium (Kalateh et al., 2008), iron (Amani et al., 2007), platin (Amani et al., 2009), copper (Albada et al., 2004) and mercury (Tadayon Pour et al., 2008; Alizadeh et al., 2010). Here, we report the synthesis and structure of the title compound.
The asymmetric unit of the title compound, (Fig. 1), contains two crystallographically independent [In(C12H12N2)Cl3(C3H7NO)] molecules and one water solvent molecule. 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 dimethylformamide and three Cl atoms. The In—Cl, In—O and In—N bond lengths and angles are collected in Table 1.
In the crystal structure, intermolecular O—H···Cl and C—H···O and C—H···Cl hydrogen bonds link the molecules (Fig. 2 & Table 2).