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metal-organic compounds
Trichlorido(dimethyl sulfoxide-κO)(di-2-pyridylamine-κ2N,N′)indium(III)
aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran, and bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
*Correspondence e-mail: sadif_shirvan1@yahoo.com
In the title compound, [InCl3(C10H9N3)(C2H6OS)], the InIII atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating di-2-pyridylamine ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. Intermolecular C—H⋯Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distance = 3.510 (3) Å] are present in the crystal.
Related literature
For related structures, see: Abedi et al. (2011, 2012a
,b
); Ahmadi et al. (2008
); Clemente (2005
); Dong et al. (1987
); Ilyuhin & Malyarik (1994
); Kalateh, Ahmadi et al. (2008
); Kalateh, Norouzi et al. (2008
); Malecki et al. (2011
); Malyarick et al. (1992
); Shi & Jiang (2006
); Shirvan & Haydari Dezfuli (2012
); Yoshikawa et al. (2004
); Yousefi et al. (2009
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2007); cell 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
); software used to prepare material for publication: SHELXTL (Sheldrick, 2008)
.
Supporting information
https://doi.org/10.1107/S1600536812038147/hy2584sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038147/hy2584Isup2.hkl
For the preparation of the title compound, a solution of di-2-pyridylamine (0.29 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) at room temperature. The suitable crystals for X-ray
were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.57 g, 73.4%).All H atoms were positioned geometrically, with C—H = 0.93 (CH), 0.96 (CH3) and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N).
Recently, we reported the synthesis and
of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine). Several InIII complexes with a formula [In(L1)Cl3(L2)] (L1 = an N,N'-chelating ligand, L2 = DMSO, H2O, MeOH or EtOH), such as [In(bipy)Cl3(H2O)], (III), [In(bipy)Cl3(EtOH)], (IV), [In(bipy)Cl3(H2O)].H2O, (V) (Malyarick et al., 1992), [In(phen)Cl3(DMSO)], (VI) (Dong et al., 1987), [In(phen)Cl3(H2O)], (VII), [In(phen)Cl3(EtOH)].EtOH, (VIII) (Ilyuhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl3(DMSO)], (IX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl3(MeOH)], (X) (Kalateh, Ahmadi et al., 2008), [In(4,4'-dtbipy)Cl3(MeOH)].0.5MeOH, (XI) (Abedi et al., 2012a), [In(4bt)Cl3(MeOH)], (XII) and [In(4bt)Cl3(DMSO)], (XIII) (Abedi et al., 2012b) (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, 4,4'-dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. Di-2-pyridylamine (DPA) is a good bidentate ligand, and numerous complexes with DPA have been prepared, such as that of [Hg(DPA)Br2], (XIV) (Kalateh, Norouzi et al., 2008), [Hg(DPA)Cl2], (XV) (Yousefi et al., 2009), [Pt(DPA)Cl4].DMF, (XVI) (Abedi et al., 2011), [Ir(DPA)2Cl2](PF6), (XVII) (Yoshikawa et al., 2004), [Cu(DPA)2](BF4)2, (XVIII) (Clemente, 2005), [Mn(DPA)2(NCS)2].0.5H2O, (XIX) (Malecki et al., 2011) and [Au(DPA)Cl2]Cl, (XX) (Shi & Jiang, 2006). We report herein the synthesis and of the title compound, (I).In the title compound (Fig. 1), the InIII atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating DPA ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg3···Cg3i [symmetry code: (i) -x, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring], with a centroid–centroid distance of 3.510 (3) Å, stabilize the structure.
For related structures, see: Abedi et al. (2011, 2012a,b); Ahmadi et al. (2008); Clemente (2005); Dong et al. (1987); Ilyuhin & Malyarik (1994); Kalateh, Ahmadi et al. (2008); Kalateh, Norouzi et al. (2008); Malecki et al. (2011); Malyarick et al. (1992); Shi & Jiang (2006); Shirvan & Haydari Dezfuli (2012); Yoshikawa et al. (2004); Yousefi et al. (2009).
Data collection: APEX2 (Bruker, 2007); cell
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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[InCl3(C10H9N3)(C2H6OS)] | F(000) = 1856 |
Mr = 470.51 | Dx = 1.784 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 14020 reflections |
a = 29.283 (2) Å | θ = 2.6–26.0° |
b = 7.7642 (7) Å | µ = 1.93 mm−1 |
c = 15.9459 (12) Å | T = 298 K |
β = 104.891 (6)° | Block, colorless |
V = 3503.7 (5) Å3 | 0.20 × 0.18 × 0.15 mm |
Z = 8 |
Bruker APEXII CCD diffractometer | 3448 independent reflections |
Radiation source: fine-focus sealed tube | 2503 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
φ and ω scans | θmax = 26.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −29→36 |
Tmin = 0.702, Tmax = 0.796 | k = −9→9 |
14020 measured reflections | l = −19→19 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0384P)2] where P = (Fo2 + 2Fc2)/3 |
3448 reflections | (Δ/σ)max = 0.007 |
192 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
[InCl3(C10H9N3)(C2H6OS)] | V = 3503.7 (5) Å3 |
Mr = 470.51 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 29.283 (2) Å | µ = 1.93 mm−1 |
b = 7.7642 (7) Å | T = 298 K |
c = 15.9459 (12) Å | 0.20 × 0.18 × 0.15 mm |
β = 104.891 (6)° |
Bruker APEXII CCD diffractometer | 3448 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2503 reflections with I > 2σ(I) |
Tmin = 0.702, Tmax = 0.796 | Rint = 0.075 |
14020 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.72 e Å−3 |
3448 reflections | Δρmin = −0.61 e Å−3 |
192 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 | 0.1269 (2) | 0.2012 (6) | 0.2648 (3) | 0.0416 (13) | |
H1 | 0.1292 | 0.3198 | 0.2730 | 0.050* | |
C2 | 0.1331 (2) | 0.0973 (7) | 0.3361 (4) | 0.0444 (13) | |
H2 | 0.1397 | 0.1439 | 0.3916 | 0.053* | |
C3 | 0.12911 (19) | −0.0815 (7) | 0.3234 (4) | 0.0422 (13) | |
H3 | 0.1334 | −0.1557 | 0.3705 | 0.051* | |
C4 | 0.11901 (18) | −0.1440 (6) | 0.2417 (3) | 0.0363 (12) | |
H4 | 0.1167 | −0.2623 | 0.2325 | 0.044* | |
C5 | 0.11200 (16) | −0.0330 (6) | 0.1712 (3) | 0.0301 (10) | |
C6 | 0.07132 (16) | −0.0304 (5) | 0.0123 (3) | 0.0276 (10) | |
C7 | 0.04239 (18) | −0.1417 (6) | −0.0476 (3) | 0.0367 (12) | |
H7 | 0.0439 | −0.2600 | −0.0381 | 0.044* | |
C8 | 0.01195 (19) | −0.0754 (7) | −0.1202 (3) | 0.0433 (13) | |
H8 | −0.0075 | −0.1478 | −0.1605 | 0.052* | |
C9 | 0.01051 (18) | 0.1023 (7) | −0.1329 (3) | 0.0415 (13) | |
H9 | −0.0105 | 0.1510 | −0.1810 | 0.050* | |
C10 | 0.04049 (17) | 0.2029 (6) | −0.0735 (3) | 0.0355 (12) | |
H10 | 0.0393 | 0.3215 | −0.0819 | 0.043* | |
C11 | 0.2689 (2) | 0.1898 (9) | 0.1207 (5) | 0.0667 (19) | |
H11A | 0.2654 | 0.3090 | 0.1337 | 0.080* | |
H11B | 0.2735 | 0.1797 | 0.0635 | 0.080* | |
H11C | 0.2957 | 0.1425 | 0.1622 | 0.080* | |
C12 | 0.2306 (3) | −0.1246 (8) | 0.0852 (6) | 0.090 (3) | |
H12A | 0.2358 | −0.1087 | 0.0286 | 0.108* | |
H12B | 0.2047 | −0.2024 | 0.0812 | 0.108* | |
H12C | 0.2586 | −0.1717 | 0.1236 | 0.108* | |
N1 | 0.11766 (14) | 0.1385 (4) | 0.1824 (3) | 0.0320 (9) | |
N2 | 0.09923 (15) | −0.1004 (5) | 0.0877 (3) | 0.0341 (10) | |
H2B | 0.1104 | −0.2010 | 0.0822 | 0.041* | |
N3 | 0.07196 (13) | 0.1395 (4) | −0.0027 (2) | 0.0289 (9) | |
O1 | 0.17759 (11) | 0.1461 (4) | 0.0516 (2) | 0.0371 (8) | |
In1 | 0.124091 (13) | 0.32946 (4) | 0.07746 (2) | 0.02991 (11) | |
Cl1 | 0.12945 (6) | 0.49624 (17) | −0.04921 (10) | 0.0507 (4) | |
Cl2 | 0.18785 (6) | 0.48512 (18) | 0.17913 (10) | 0.0562 (4) | |
Cl3 | 0.05889 (5) | 0.49583 (15) | 0.10961 (9) | 0.0437 (3) | |
S1 | 0.21736 (5) | 0.07577 (18) | 0.12573 (10) | 0.0435 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.051 (3) | 0.035 (3) | 0.038 (3) | 0.005 (2) | 0.010 (3) | −0.001 (2) |
C2 | 0.054 (4) | 0.045 (3) | 0.033 (3) | 0.005 (3) | 0.010 (3) | −0.006 (2) |
C3 | 0.043 (3) | 0.047 (3) | 0.039 (3) | 0.009 (2) | 0.013 (3) | 0.013 (2) |
C4 | 0.045 (3) | 0.021 (2) | 0.044 (3) | 0.005 (2) | 0.012 (2) | 0.004 (2) |
C5 | 0.024 (2) | 0.030 (2) | 0.035 (3) | 0.0034 (19) | 0.007 (2) | −0.001 (2) |
C6 | 0.029 (3) | 0.023 (2) | 0.031 (3) | −0.0002 (18) | 0.008 (2) | 0.0012 (18) |
C7 | 0.042 (3) | 0.026 (2) | 0.042 (3) | −0.006 (2) | 0.011 (2) | −0.006 (2) |
C8 | 0.040 (3) | 0.054 (3) | 0.034 (3) | −0.011 (3) | 0.006 (3) | −0.013 (2) |
C9 | 0.030 (3) | 0.058 (3) | 0.034 (3) | 0.002 (2) | 0.003 (2) | 0.003 (2) |
C10 | 0.037 (3) | 0.032 (3) | 0.038 (3) | 0.005 (2) | 0.011 (2) | 0.004 (2) |
C11 | 0.040 (3) | 0.089 (5) | 0.066 (4) | −0.002 (3) | 0.005 (3) | 0.027 (4) |
C12 | 0.077 (5) | 0.051 (4) | 0.134 (8) | 0.032 (4) | 0.014 (5) | 0.002 (4) |
N1 | 0.041 (2) | 0.0216 (19) | 0.032 (2) | 0.0007 (16) | 0.0073 (19) | 0.0021 (15) |
N2 | 0.048 (3) | 0.0181 (16) | 0.033 (2) | 0.0054 (17) | 0.004 (2) | −0.0015 (16) |
N3 | 0.030 (2) | 0.0252 (19) | 0.029 (2) | 0.0008 (15) | 0.0041 (18) | 0.0008 (15) |
O1 | 0.0319 (18) | 0.0387 (18) | 0.0377 (19) | 0.0067 (15) | 0.0035 (15) | −0.0017 (15) |
In1 | 0.03548 (19) | 0.01872 (14) | 0.03429 (18) | −0.00068 (16) | 0.00671 (13) | −0.00053 (15) |
Cl1 | 0.0634 (9) | 0.0369 (6) | 0.0565 (9) | 0.0011 (6) | 0.0239 (8) | 0.0158 (6) |
Cl2 | 0.0556 (9) | 0.0504 (8) | 0.0572 (9) | −0.0182 (7) | 0.0048 (8) | −0.0175 (7) |
Cl3 | 0.0470 (8) | 0.0267 (6) | 0.0591 (8) | 0.0062 (5) | 0.0170 (7) | −0.0020 (5) |
S1 | 0.0354 (7) | 0.0489 (8) | 0.0454 (8) | 0.0085 (6) | 0.0092 (6) | 0.0139 (6) |
C1—N1 | 1.362 (7) | C9—H9 | 0.9300 |
C1—C2 | 1.368 (8) | C10—N3 | 1.353 (6) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.403 (7) | C11—S1 | 1.768 (6) |
C2—H2 | 0.9300 | C11—H11A | 0.9600 |
C3—C4 | 1.350 (7) | C11—H11B | 0.9600 |
C3—H3 | 0.9300 | C11—H11C | 0.9600 |
C4—C5 | 1.389 (7) | C12—S1 | 1.766 (7) |
C4—H4 | 0.9300 | C12—H12A | 0.9600 |
C5—N1 | 1.347 (5) | C12—H12B | 0.9600 |
C5—N2 | 1.390 (6) | C12—H12C | 0.9600 |
C6—N3 | 1.342 (5) | N1—In1 | 2.279 (4) |
C6—N2 | 1.380 (6) | N2—H2B | 0.8600 |
C6—C7 | 1.401 (6) | N3—In1 | 2.267 (4) |
C7—C8 | 1.367 (7) | O1—S1 | 1.531 (3) |
C7—H7 | 0.9300 | O1—In1 | 2.232 (3) |
C8—C9 | 1.394 (8) | In1—Cl1 | 2.4381 (14) |
C8—H8 | 0.9300 | In1—Cl2 | 2.4535 (14) |
C9—C10 | 1.361 (7) | In1—Cl3 | 2.4658 (13) |
N1—C1—C2 | 122.8 (5) | H11B—C11—H11C | 109.5 |
N1—C1—H1 | 118.6 | S1—C12—H12A | 109.5 |
C2—C1—H1 | 118.6 | S1—C12—H12B | 109.5 |
C1—C2—C3 | 118.4 (5) | H12A—C12—H12B | 109.5 |
C1—C2—H2 | 120.8 | S1—C12—H12C | 109.5 |
C3—C2—H2 | 120.8 | H12A—C12—H12C | 109.5 |
C4—C3—C2 | 119.0 (5) | H12B—C12—H12C | 109.5 |
C4—C3—H3 | 120.5 | C5—N1—C1 | 117.9 (4) |
C2—C3—H3 | 120.5 | C5—N1—In1 | 125.2 (3) |
C3—C4—C5 | 120.5 (4) | C1—N1—In1 | 116.2 (3) |
C3—C4—H4 | 119.7 | C6—N2—C5 | 129.8 (4) |
C5—C4—H4 | 119.7 | C6—N2—H2B | 115.1 |
N1—C5—C4 | 121.2 (4) | C5—N2—H2B | 115.1 |
N1—C5—N2 | 119.5 (4) | C6—N3—C10 | 118.0 (4) |
C4—C5—N2 | 119.3 (4) | C6—N3—In1 | 125.2 (3) |
N3—C6—N2 | 120.7 (4) | C10—N3—In1 | 116.7 (3) |
N3—C6—C7 | 121.2 (4) | S1—O1—In1 | 121.04 (19) |
N2—C6—C7 | 118.0 (4) | O1—In1—N3 | 83.32 (13) |
C8—C7—C6 | 119.6 (4) | O1—In1—N1 | 85.12 (13) |
C8—C7—H7 | 120.2 | N3—In1—N1 | 79.63 (13) |
C6—C7—H7 | 120.2 | O1—In1—Cl1 | 89.31 (9) |
C7—C8—C9 | 119.0 (5) | N3—In1—Cl1 | 93.18 (10) |
C7—C8—H8 | 120.5 | N1—In1—Cl1 | 171.37 (10) |
C9—C8—H8 | 120.5 | O1—In1—Cl2 | 89.15 (9) |
C10—C9—C8 | 118.5 (5) | N3—In1—Cl2 | 168.87 (10) |
C10—C9—H9 | 120.8 | N1—In1—Cl2 | 91.60 (10) |
C8—C9—H9 | 120.8 | Cl1—In1—Cl2 | 94.92 (5) |
N3—C10—C9 | 123.4 (4) | O1—In1—Cl3 | 171.97 (9) |
N3—C10—H10 | 118.3 | N3—In1—Cl3 | 90.74 (10) |
C9—C10—H10 | 118.3 | N1—In1—Cl3 | 88.50 (10) |
S1—C11—H11A | 109.5 | Cl1—In1—Cl3 | 96.44 (5) |
S1—C11—H11B | 109.5 | Cl2—In1—Cl3 | 95.91 (5) |
H11A—C11—H11B | 109.5 | O1—S1—C12 | 103.1 (3) |
S1—C11—H11C | 109.5 | O1—S1—C11 | 106.0 (3) |
H11A—C11—H11C | 109.5 | C12—S1—C11 | 98.9 (4) |
N1—C1—C2—C3 | −0.7 (9) | C9—C10—N3—In1 | 172.6 (4) |
C1—C2—C3—C4 | −0.6 (8) | S1—O1—In1—N3 | −128.7 (2) |
C2—C3—C4—C5 | −0.9 (8) | S1—O1—In1—N1 | −48.6 (2) |
C3—C4—C5—N1 | 3.8 (8) | S1—O1—In1—Cl1 | 138.0 (2) |
C3—C4—C5—N2 | −176.7 (5) | S1—O1—In1—Cl2 | 43.1 (2) |
N3—C6—C7—C8 | −4.3 (8) | C6—N3—In1—O1 | 53.4 (4) |
N2—C6—C7—C8 | 175.6 (5) | C10—N3—In1—O1 | −123.6 (3) |
C6—C7—C8—C9 | 0.1 (8) | C6—N3—In1—N1 | −32.9 (4) |
C7—C8—C9—C10 | 1.7 (8) | C10—N3—In1—N1 | 150.2 (4) |
C8—C9—C10—N3 | 0.5 (8) | C6—N3—In1—Cl1 | 142.3 (4) |
C4—C5—N1—C1 | −5.0 (7) | C10—N3—In1—Cl1 | −34.6 (3) |
N2—C5—N1—C1 | 175.5 (4) | C6—N3—In1—Cl2 | 5.6 (8) |
C4—C5—N1—In1 | 165.3 (4) | C10—N3—In1—Cl2 | −171.3 (4) |
N2—C5—N1—In1 | −14.3 (6) | C6—N3—In1—Cl3 | −121.2 (4) |
C2—C1—N1—C5 | 3.5 (8) | C10—N3—In1—Cl3 | 61.9 (3) |
C2—C1—N1—In1 | −167.6 (4) | C5—N1—In1—O1 | −48.7 (4) |
N3—C6—N2—C5 | 35.4 (8) | C1—N1—In1—O1 | 121.6 (4) |
C7—C6—N2—C5 | −144.5 (5) | C5—N1—In1—N3 | 35.3 (4) |
N1—C5—N2—C6 | −32.5 (7) | C1—N1—In1—N3 | −154.3 (4) |
C4—C5—N2—C6 | 147.9 (5) | C5—N1—In1—Cl2 | −137.7 (4) |
N2—C6—N3—C10 | −173.5 (4) | C1—N1—In1—Cl2 | 32.6 (4) |
C7—C6—N3—C10 | 6.4 (7) | C5—N1—In1—Cl3 | 126.4 (4) |
N2—C6—N3—In1 | 9.6 (6) | C1—N1—In1—Cl3 | −63.2 (4) |
C7—C6—N3—In1 | −170.5 (3) | In1—O1—S1—C12 | 153.0 (3) |
C9—C10—N3—C6 | −4.5 (7) | In1—O1—S1—C11 | −103.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11C···Cl2i | 0.96 | 2.74 | 3.499 (8) | 137 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [InCl3(C10H9N3)(C2H6OS)] |
Mr | 470.51 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 29.283 (2), 7.7642 (7), 15.9459 (12) |
β (°) | 104.891 (6) |
V (Å3) | 3503.7 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.93 |
Crystal size (mm) | 0.20 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.702, 0.796 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14020, 3448, 2503 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.080, 0.99 |
No. of reflections | 3448 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.61 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11C···Cl2i | 0.96 | 2.74 | 3.499 (8) | 137 |
Symmetry code: (i) −x+1/2, 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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Recently, we reported the synthesis and crystal structure of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine). Several InIII complexes with a formula [In(L1)Cl3(L2)] (L1 = an N,N'-chelating ligand, L2 = DMSO, H2O, MeOH or EtOH), such as [In(bipy)Cl3(H2O)], (III), [In(bipy)Cl3(EtOH)], (IV), [In(bipy)Cl3(H2O)].H2O, (V) (Malyarick et al., 1992), [In(phen)Cl3(DMSO)], (VI) (Dong et al., 1987), [In(phen)Cl3(H2O)], (VII), [In(phen)Cl3(EtOH)].EtOH, (VIII) (Ilyuhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl3(DMSO)], (IX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl3(MeOH)], (X) (Kalateh, Ahmadi et al., 2008), [In(4,4'-dtbipy)Cl3(MeOH)].0.5MeOH, (XI) (Abedi et al., 2012a), [In(4bt)Cl3(MeOH)], (XII) and [In(4bt)Cl3(DMSO)], (XIII) (Abedi et al., 2012b) (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, 4,4'-dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. Di-2-pyridylamine (DPA) is a good bidentate ligand, and numerous complexes with DPA have been prepared, such as that of [Hg(DPA)Br2], (XIV) (Kalateh, Norouzi et al., 2008), [Hg(DPA)Cl2], (XV) (Yousefi et al., 2009), [Pt(DPA)Cl4].DMF, (XVI) (Abedi et al., 2011), [Ir(DPA)2Cl2](PF6), (XVII) (Yoshikawa et al., 2004), [Cu(DPA)2](BF4)2, (XVIII) (Clemente, 2005), [Mn(DPA)2(NCS)2].0.5H2O, (XIX) (Malecki et al., 2011) and [Au(DPA)Cl2]Cl, (XX) (Shi & Jiang, 2006). 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 geometry by two N atoms from a chelating DPA ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg3···Cg3i [symmetry code: (i) -x, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring], with a centroid–centroid distance of 3.510 (3) Å, stabilize the structure.