metal-organic compounds
cis-Chloridobis(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)oxidovanadium(IV) chloride ethanol monosolvate monohydrate
aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran, and bDepartment of Petroleum Engineering, Islamic Azad University, Omidieh Branch, Omidieh, Iran
*Correspondence e-mail: sadif_shirvan1@yahoo.com
In the title compound, [VClO(C12H12N2)2]Cl·C2H5OH·H2O, the VIV atom is six-coordinated in a distorted octahedral geometry by four N atoms from two 4,4′-dimethyl-2,2′-bipyridine ligands, one O atom and one Cl atom. In the crystal, O—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distances = 3.7236 (17) and 3.6026 (19) Å] stabilize the structure. Intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds are also present.
Related literature
For related structures, see: Ahmadi et al. (2008); Alizadeh et al. (2010); Amani et al. (2009); Hojjat Kashani et al. (2008); Kalateh et al. (2008, 2010); Shirvan & Haydari Dezfuli (2011, 2012a,b); Triantafillou et al. (2004); Yousefi et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: SMART (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: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812040251/hy2588sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040251/hy2588Isup2.hkl
For the preparation of the title compound, a solution of 4,4'-dimethyl-2,2'-bipyridine (0.29 g, 1.60 mmol) in ethanol (20 ml) was added to a solution of VCl3 (0.13 g, 0.80 mmol) in water (4 ml) and the resulting violet solution was stirred at 323 K for 40 min. Then, it was left to evaporate slowly at room temperature. After six days, green prismatic crystals of the title compound were isolated (yield: 0.32 g, 74.0%).
H atoms bonded to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 (aromatic), 0.99 (CH2) and 0.98 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). H atoms of hydroxyl group and water molecules were located in a difference Fourier map and refined as riding atoms, with Uiso(H) = 1.2Ueq(O). There is a high residual peak of 2.09 e Å-3 near V1 atom due to the absorption effects that could not be correctly account for. The highest residual electron density was found at 0.84 Å from V1 atom and the deepest hole at 0.65 Å from V1 atom.
Recently, we reported the synthesis and crystal structures of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012b), and [CdBr2(4,4'-dmbipy)(DMSO)], (III) (Shirvan & Haydari Dezfuli, 2012a) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 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], (IV) (Yousefi et al., 2008), [Hg(4,4'-dmbipy)Br2], (V) (Kalateh et al., 2008), [Fe(4,4'-dmbipy)Cl3(DMSO)], (VI) (Amani et al., 2009), [Pt(4,4'-dmbipy)Cl4], (VII) (Hojjat Kashani et al., 2008), [Cd(4,4'-dmbipy)I2(DMSO)], (VIII) (Kalateh et al., 2010), [Zn(4,4'-dmbipy)Br2], (IX) (Alizadeh et al., 2010), [Zn(4,4'-dmbipy)(H2O)(NO3)2], (X) (Shirvan & Haydari Dezfuli, 2011) and [In(4,4'-dmbpy)Cl3(DMSO)], (XI) (Ahmadi et al., 2008). We report herein the synthesis and
of the title compound, (I).In the title compound (Fig. 1), the VIV atom is six-coordinated in a distorted octahedral geometry by four N atoms from two 4,4'-dmbipy ligands, one O atom and one Cl atom. There are also one ethanol and one water solvent molecules in the
The V—Cl, V—N and V—O bond lengths and angles are in good agreement with the corresponding values in [VOCl(dtbipy)Cl]Cl.CH2Cl2 (Triantafillou et al., 2004) (dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine).In the crystal, intermolecular O—H···Cl, C—H···O and C—H···Cl hydrogen bonds, intramolecular C—H···O and C—H···Cl hydrogen bonds (Table 1) and π–π contacts between the pyridine rings (Fig. 2), Cg3···Cg4i and Cg5···Cg6ii, with centroid–centroid distances of 3.7236 (17) and 3.6026 (19) Å [symmetry codes: (i) 1-x, 1-y, 1-z; (ii) -x, 1-y, 2-z. Cg3, Cg4, Cg5 and Cg6 are the centroids of the N1/C1–C5, N2/C6–C10, N3/C13–C17 and N4/C18–C22 rings, respectively], stabilize the structure.
For related structures, see: Ahmadi et al. (2008); Alizadeh et al. (2010); Amani et al. (2009); Hojjat Kashani et al. (2008); Kalateh et al. (2008, 2010); Shirvan & Haydari Dezfuli (2011, 2012a,b); Triantafillou et al. (2004); Yousefi et al. (2008).
Data collection: SMART (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: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. |
[VClO(C12H12N2)2]Cl·C2H6O·H2O | Z = 2 |
Mr = 570.40 | F(000) = 594 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6955 (11) Å | Cell parameters from 600 reflections |
b = 10.9905 (12) Å | θ = 3.0–26.0° |
c = 14.5739 (17) Å | µ = 0.59 mm−1 |
α = 68.711 (2)° | T = 120 K |
β = 72.401 (2)° | Prism, green |
γ = 81.381 (2)° | 0.32 × 0.14 × 0.09 mm |
V = 1377.9 (3) Å3 |
Bruker SMART 1000 CCD diffractometer | 5363 independent reflections |
Radiation source: fine-focus sealed tube | 4398 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.926, Tmax = 0.954 | k = −13→13 |
12257 measured reflections | l = −17→17 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.048P)2 + 3.916P] where P = (Fo2 + 2Fc2)/3 |
5363 reflections | (Δ/σ)max < 0.001 |
330 parameters | Δρmax = 2.09 e Å−3 |
0 restraints | Δρmin = −0.89 e Å−3 |
[VClO(C12H12N2)2]Cl·C2H6O·H2O | γ = 81.381 (2)° |
Mr = 570.40 | V = 1377.9 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6955 (11) Å | Mo Kα radiation |
b = 10.9905 (12) Å | µ = 0.59 mm−1 |
c = 14.5739 (17) Å | T = 120 K |
α = 68.711 (2)° | 0.32 × 0.14 × 0.09 mm |
β = 72.401 (2)° |
Bruker SMART 1000 CCD diffractometer | 5363 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4398 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 0.954 | Rint = 0.026 |
12257 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.00 | Δρmax = 2.09 e Å−3 |
5363 reflections | Δρmin = −0.89 e Å−3 |
330 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 | ||
V1 | 0.17871 (6) | 0.53590 (5) | 0.73759 (4) | 0.02822 (16) | |
Cl1 | 0.10808 (9) | 0.45573 (9) | 0.63211 (6) | 0.0368 (2) | |
O1 | 0.0514 (2) | 0.6517 (2) | 0.74454 (15) | 0.0278 (5) | |
N1 | 0.3293 (3) | 0.6612 (3) | 0.61322 (19) | 0.0269 (6) | |
N2 | 0.3918 (3) | 0.4168 (2) | 0.71332 (19) | 0.0259 (6) | |
N4 | 0.0941 (3) | 0.3772 (3) | 0.86974 (19) | 0.0252 (5) | |
N3 | 0.2635 (3) | 0.5586 (3) | 0.84871 (18) | 0.0240 (5) | |
C1 | 0.2904 (4) | 0.7853 (3) | 0.5636 (2) | 0.0312 (7) | |
H1B | 0.1937 | 0.8162 | 0.5863 | 0.037* | |
C2 | 0.3840 (4) | 0.8699 (3) | 0.4815 (2) | 0.0327 (7) | |
H2A | 0.3525 | 0.9572 | 0.4496 | 0.039* | |
C3 | 0.5253 (4) | 0.8251 (3) | 0.4462 (2) | 0.0320 (7) | |
C4 | 0.5655 (4) | 0.6968 (3) | 0.4970 (2) | 0.0302 (7) | |
H4A | 0.6610 | 0.6634 | 0.4745 | 0.036* | |
C5 | 0.4672 (4) | 0.6175 (3) | 0.5801 (2) | 0.0263 (7) | |
C6 | 0.5039 (3) | 0.4814 (3) | 0.6387 (2) | 0.0260 (6) | |
C7 | 0.6429 (4) | 0.4240 (3) | 0.6201 (2) | 0.0301 (7) | |
H7A | 0.7195 | 0.4724 | 0.5674 | 0.036* | |
C8 | 0.6698 (4) | 0.2963 (3) | 0.6784 (2) | 0.0308 (7) | |
C9 | 0.5540 (4) | 0.2300 (3) | 0.7545 (2) | 0.0304 (7) | |
H9A | 0.5676 | 0.1422 | 0.7961 | 0.036* | |
C10 | 0.4187 (4) | 0.2928 (3) | 0.7691 (2) | 0.0279 (7) | |
H10A | 0.3406 | 0.2458 | 0.8213 | 0.033* | |
C11 | 0.6322 (4) | 0.9131 (4) | 0.3567 (3) | 0.0401 (9) | |
H11A | 0.5933 | 0.9458 | 0.2970 | 0.060* | |
H11B | 0.7239 | 0.8636 | 0.3412 | 0.060* | |
H11C | 0.6488 | 0.9870 | 0.3740 | 0.060* | |
C12 | 0.8190 (4) | 0.2308 (4) | 0.6607 (3) | 0.0419 (9) | |
H12A | 0.8857 | 0.2776 | 0.6735 | 0.063* | |
H12B | 0.8531 | 0.2321 | 0.5898 | 0.063* | |
H12C | 0.8151 | 0.1401 | 0.7072 | 0.063* | |
C13 | 0.3489 (3) | 0.6528 (3) | 0.8329 (2) | 0.0271 (7) | |
H13A | 0.3865 | 0.7092 | 0.7648 | 0.033* | |
C14 | 0.3850 (3) | 0.6718 (3) | 0.9109 (2) | 0.0290 (7) | |
H14A | 0.4462 | 0.7401 | 0.8964 | 0.035* | |
C15 | 0.3314 (3) | 0.5907 (3) | 1.0113 (2) | 0.0284 (7) | |
C16 | 0.2466 (3) | 0.4899 (3) | 1.0274 (2) | 0.0268 (7) | |
H16A | 0.2111 | 0.4304 | 1.0945 | 0.032* | |
C17 | 0.2136 (3) | 0.4755 (3) | 0.9458 (2) | 0.0235 (6) | |
C18 | 0.1223 (3) | 0.3723 (3) | 0.9571 (2) | 0.0229 (6) | |
C19 | 0.0696 (3) | 0.2746 (3) | 1.0491 (2) | 0.0267 (6) | |
H19A | 0.0920 | 0.2722 | 1.1088 | 0.032* | |
C20 | −0.0157 (3) | 0.1802 (3) | 1.0546 (2) | 0.0284 (7) | |
C21 | −0.0451 (3) | 0.1869 (3) | 0.9656 (3) | 0.0309 (7) | |
H21A | −0.1036 | 0.1243 | 0.9663 | 0.037* | |
C22 | 0.0116 (3) | 0.2859 (3) | 0.8754 (2) | 0.0291 (7) | |
H22A | −0.0090 | 0.2892 | 0.8148 | 0.035* | |
C23 | 0.3648 (4) | 0.6126 (4) | 1.0986 (3) | 0.0380 (8) | |
H23A | 0.3052 | 0.5570 | 1.1637 | 0.057* | |
H23B | 0.3434 | 0.7046 | 1.0933 | 0.057* | |
H23C | 0.4675 | 0.5905 | 1.0955 | 0.057* | |
C24 | −0.0717 (4) | 0.0744 (3) | 1.1545 (3) | 0.0384 (8) | |
H24A | −0.1447 | 0.0271 | 1.1483 | 0.058* | |
H24B | −0.1156 | 0.1133 | 1.2080 | 0.058* | |
H24C | 0.0085 | 0.0135 | 1.1724 | 0.058* | |
Cl2 | 0.35132 (10) | 0.10613 (9) | 0.13262 (9) | 0.0482 (3) | |
O1S | 0.3730 (3) | 0.1709 (3) | 0.3197 (2) | 0.0526 (7) | |
H1S | 0.3480 | 0.1380 | 0.2767 | 0.063* | |
O1W | 0.3211 (3) | 0.0038 (3) | 0.9589 (2) | 0.0505 (7) | |
H1W | 0.2964 | 0.0315 | 1.0088 | 0.061* | |
H2W | 0.4102 | −0.0247 | 0.9268 | 0.061* | |
C1S | 0.2544 (5) | 0.2599 (4) | 0.3334 (3) | 0.0511 (10) | |
H1SA | 0.2162 | 0.2901 | 0.2726 | 0.061* | |
H1SB | 0.2877 | 0.3371 | 0.3391 | 0.061* | |
C2S | 0.1359 (5) | 0.2007 (6) | 0.4266 (3) | 0.0722 (15) | |
H2SA | 0.0615 | 0.2685 | 0.4382 | 0.108* | |
H2SB | 0.1756 | 0.1620 | 0.4859 | 0.108* | |
H2SC | 0.0927 | 0.1326 | 0.4170 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0275 (3) | 0.0332 (3) | 0.0219 (3) | −0.0078 (2) | −0.0058 (2) | −0.0050 (2) |
Cl1 | 0.0360 (5) | 0.0488 (5) | 0.0279 (4) | −0.0096 (4) | −0.0037 (3) | −0.0165 (4) |
O1 | 0.0276 (11) | 0.0311 (11) | 0.0173 (10) | −0.0014 (9) | 0.0052 (8) | −0.0089 (9) |
N1 | 0.0318 (14) | 0.0295 (14) | 0.0196 (12) | −0.0053 (11) | −0.0031 (11) | −0.0102 (11) |
N2 | 0.0328 (14) | 0.0264 (13) | 0.0188 (12) | −0.0083 (11) | −0.0039 (11) | −0.0078 (10) |
N4 | 0.0222 (13) | 0.0311 (14) | 0.0208 (12) | −0.0054 (10) | −0.0019 (10) | −0.0086 (11) |
N3 | 0.0203 (12) | 0.0307 (13) | 0.0196 (12) | −0.0037 (10) | −0.0018 (10) | −0.0088 (10) |
C1 | 0.0371 (18) | 0.0299 (17) | 0.0264 (16) | −0.0033 (14) | −0.0077 (14) | −0.0094 (13) |
C2 | 0.043 (2) | 0.0282 (16) | 0.0235 (16) | −0.0093 (14) | −0.0060 (14) | −0.0045 (13) |
C3 | 0.043 (2) | 0.0338 (17) | 0.0197 (15) | −0.0132 (15) | −0.0029 (14) | −0.0100 (13) |
C4 | 0.0326 (17) | 0.0341 (17) | 0.0258 (16) | −0.0071 (14) | −0.0014 (13) | −0.0153 (14) |
C5 | 0.0341 (17) | 0.0289 (16) | 0.0192 (14) | −0.0075 (13) | −0.0055 (12) | −0.0107 (12) |
C6 | 0.0307 (16) | 0.0304 (16) | 0.0188 (14) | −0.0069 (13) | −0.0023 (12) | −0.0120 (12) |
C7 | 0.0307 (17) | 0.0334 (17) | 0.0248 (16) | −0.0082 (13) | 0.0006 (13) | −0.0122 (13) |
C8 | 0.0311 (17) | 0.0384 (18) | 0.0293 (16) | −0.0005 (14) | −0.0070 (13) | −0.0200 (14) |
C9 | 0.0348 (18) | 0.0301 (16) | 0.0271 (16) | −0.0024 (14) | −0.0057 (14) | −0.0125 (13) |
C10 | 0.0310 (17) | 0.0276 (16) | 0.0241 (15) | −0.0063 (13) | −0.0021 (13) | −0.0099 (13) |
C11 | 0.051 (2) | 0.0370 (19) | 0.0270 (17) | −0.0181 (17) | 0.0017 (16) | −0.0083 (15) |
C12 | 0.0327 (19) | 0.048 (2) | 0.045 (2) | 0.0002 (16) | −0.0086 (16) | −0.0181 (18) |
C13 | 0.0263 (16) | 0.0268 (15) | 0.0248 (15) | −0.0061 (12) | −0.0012 (12) | −0.0076 (13) |
C14 | 0.0266 (16) | 0.0314 (17) | 0.0303 (16) | −0.0056 (13) | −0.0029 (13) | −0.0142 (14) |
C15 | 0.0262 (16) | 0.0322 (17) | 0.0306 (17) | 0.0024 (13) | −0.0085 (13) | −0.0156 (14) |
C16 | 0.0269 (16) | 0.0305 (16) | 0.0221 (15) | 0.0023 (13) | −0.0050 (12) | −0.0105 (13) |
C17 | 0.0211 (15) | 0.0262 (15) | 0.0224 (15) | 0.0007 (12) | −0.0041 (12) | −0.0094 (12) |
C18 | 0.0211 (14) | 0.0243 (15) | 0.0225 (14) | 0.0020 (11) | −0.0043 (12) | −0.0093 (12) |
C19 | 0.0285 (16) | 0.0271 (15) | 0.0221 (15) | −0.0012 (12) | −0.0040 (12) | −0.0077 (12) |
C20 | 0.0245 (15) | 0.0247 (15) | 0.0284 (16) | −0.0006 (12) | 0.0021 (13) | −0.0078 (13) |
C21 | 0.0254 (16) | 0.0291 (16) | 0.0347 (18) | −0.0055 (13) | −0.0035 (13) | −0.0089 (14) |
C22 | 0.0266 (16) | 0.0340 (17) | 0.0300 (17) | −0.0069 (13) | −0.0062 (13) | −0.0135 (14) |
C23 | 0.045 (2) | 0.043 (2) | 0.0341 (19) | −0.0044 (16) | −0.0155 (16) | −0.0176 (16) |
C24 | 0.041 (2) | 0.0316 (18) | 0.0310 (18) | −0.0087 (15) | 0.0018 (15) | −0.0037 (15) |
Cl2 | 0.0400 (5) | 0.0330 (5) | 0.0766 (7) | 0.0011 (4) | −0.0211 (5) | −0.0208 (5) |
O1S | 0.0405 (15) | 0.0630 (18) | 0.0399 (15) | −0.0082 (13) | −0.0101 (12) | 0.0009 (13) |
O1W | 0.0354 (14) | 0.0557 (17) | 0.0618 (18) | −0.0113 (12) | −0.0108 (13) | −0.0195 (14) |
C1S | 0.055 (3) | 0.048 (2) | 0.048 (2) | −0.004 (2) | −0.022 (2) | −0.0080 (19) |
C2S | 0.058 (3) | 0.102 (4) | 0.040 (2) | 0.012 (3) | −0.010 (2) | −0.012 (3) |
V1—O1 | 1.643 (2) | C12—H12B | 0.9800 |
V1—N4 | 2.112 (3) | C12—H12C | 0.9800 |
V1—N1 | 2.122 (3) | C13—C14 | 1.377 (5) |
V1—N3 | 2.126 (3) | C13—H13A | 0.9500 |
V1—N2 | 2.278 (3) | C14—C15 | 1.392 (5) |
V1—Cl1 | 2.3259 (10) | C14—H14A | 0.9500 |
N1—C1 | 1.349 (4) | C15—C16 | 1.388 (5) |
N1—C5 | 1.355 (4) | C15—C23 | 1.508 (4) |
N2—C10 | 1.343 (4) | C16—C17 | 1.387 (4) |
N2—C6 | 1.351 (4) | C16—H16A | 0.9500 |
N4—C22 | 1.339 (4) | C17—C18 | 1.474 (4) |
N4—C18 | 1.362 (4) | C18—C19 | 1.384 (4) |
N3—C13 | 1.334 (4) | C19—C20 | 1.387 (4) |
N3—C17 | 1.360 (4) | C19—H19A | 0.9500 |
C1—C2 | 1.381 (5) | C20—C21 | 1.385 (5) |
C1—H1B | 0.9500 | C20—C24 | 1.499 (4) |
C2—C3 | 1.392 (5) | C21—C22 | 1.384 (5) |
C2—H2A | 0.9500 | C21—H21A | 0.9500 |
C3—C4 | 1.393 (5) | C22—H22A | 0.9500 |
C3—C11 | 1.509 (4) | C23—H23A | 0.9800 |
C4—C5 | 1.385 (4) | C23—H23B | 0.9800 |
C4—H4A | 0.9500 | C23—H23C | 0.9800 |
C5—C6 | 1.480 (4) | C24—H24A | 0.9800 |
C6—C7 | 1.392 (5) | C24—H24B | 0.9800 |
C7—C8 | 1.384 (5) | C24—H24C | 0.9800 |
C7—H7A | 0.9500 | O1S—C1S | 1.408 (5) |
C8—C9 | 1.388 (5) | O1S—H1S | 0.9310 |
C8—C12 | 1.508 (5) | O1W—H1W | 0.8444 |
C9—C10 | 1.382 (5) | O1W—H2W | 0.9188 |
C9—H9A | 0.9500 | C1S—C2S | 1.493 (6) |
C10—H10A | 0.9500 | C1S—H1SA | 0.9900 |
C11—H11A | 0.9800 | C1S—H1SB | 0.9900 |
C11—H11B | 0.9800 | C2S—H2SA | 0.9800 |
C11—H11C | 0.9800 | C2S—H2SB | 0.9800 |
C12—H12A | 0.9800 | C2S—H2SC | 0.9800 |
O1—V1—N4 | 102.71 (10) | C8—C12—H12A | 109.5 |
O1—V1—N1 | 94.54 (11) | C8—C12—H12B | 109.5 |
N4—V1—N1 | 160.77 (11) | H12A—C12—H12B | 109.5 |
O1—V1—N3 | 94.03 (11) | C8—C12—H12C | 109.5 |
N4—V1—N3 | 77.27 (10) | H12A—C12—H12C | 109.5 |
N1—V1—N3 | 93.27 (10) | H12B—C12—H12C | 109.5 |
O1—V1—N2 | 165.96 (10) | N3—C13—C14 | 122.8 (3) |
N4—V1—N2 | 88.49 (10) | N3—C13—H13A | 118.6 |
N1—V1—N2 | 73.27 (10) | C14—C13—H13A | 118.6 |
N3—V1—N2 | 80.04 (9) | C13—C14—C15 | 119.8 (3) |
O1—V1—Cl1 | 98.86 (8) | C13—C14—H14A | 120.1 |
N4—V1—Cl1 | 92.74 (8) | C15—C14—H14A | 120.1 |
N1—V1—Cl1 | 92.94 (7) | C16—C15—C14 | 117.4 (3) |
N3—V1—Cl1 | 165.19 (8) | C16—C15—C23 | 121.8 (3) |
N2—V1—Cl1 | 88.91 (7) | C14—C15—C23 | 120.8 (3) |
C1—N1—C5 | 118.0 (3) | C17—C16—C15 | 120.3 (3) |
C1—N1—V1 | 121.3 (2) | C17—C16—H16A | 119.8 |
C5—N1—V1 | 120.6 (2) | C15—C16—H16A | 119.8 |
C10—N2—C6 | 117.4 (3) | N3—C17—C16 | 121.2 (3) |
C10—N2—V1 | 126.8 (2) | N3—C17—C18 | 115.4 (3) |
C6—N2—V1 | 115.8 (2) | C16—C17—C18 | 123.4 (3) |
C22—N4—C18 | 118.1 (3) | N4—C18—C19 | 121.2 (3) |
C22—N4—V1 | 125.9 (2) | N4—C18—C17 | 115.5 (3) |
C18—N4—V1 | 115.9 (2) | C19—C18—C17 | 123.3 (3) |
C13—N3—C17 | 118.5 (3) | C18—C19—C20 | 120.5 (3) |
C13—N3—V1 | 125.8 (2) | C18—C19—H19A | 119.8 |
C17—N3—V1 | 115.40 (19) | C20—C19—H19A | 119.8 |
N1—C1—C2 | 123.4 (3) | C21—C20—C19 | 117.9 (3) |
N1—C1—H1B | 118.3 | C21—C20—C24 | 122.0 (3) |
C2—C1—H1B | 118.3 | C19—C20—C24 | 120.1 (3) |
C1—C2—C3 | 118.8 (3) | C22—C21—C20 | 119.3 (3) |
C1—C2—H2A | 120.6 | C22—C21—H21A | 120.4 |
C3—C2—H2A | 120.6 | C20—C21—H21A | 120.4 |
C2—C3—C4 | 117.9 (3) | N4—C22—C21 | 123.0 (3) |
C2—C3—C11 | 121.2 (3) | N4—C22—H22A | 118.5 |
C4—C3—C11 | 121.0 (3) | C21—C22—H22A | 118.5 |
C5—C4—C3 | 120.5 (3) | C15—C23—H23A | 109.5 |
C5—C4—H4A | 119.7 | C15—C23—H23B | 109.5 |
C3—C4—H4A | 119.7 | H23A—C23—H23B | 109.5 |
N1—C5—C4 | 121.3 (3) | C15—C23—H23C | 109.5 |
N1—C5—C6 | 115.5 (3) | H23A—C23—H23C | 109.5 |
C4—C5—C6 | 123.2 (3) | H23B—C23—H23C | 109.5 |
N2—C6—C7 | 122.1 (3) | C20—C24—H24A | 109.5 |
N2—C6—C5 | 114.7 (3) | C20—C24—H24B | 109.5 |
C7—C6—C5 | 123.2 (3) | H24A—C24—H24B | 109.5 |
C8—C7—C6 | 120.1 (3) | C20—C24—H24C | 109.5 |
C8—C7—H7A | 119.9 | H24A—C24—H24C | 109.5 |
C6—C7—H7A | 119.9 | H24B—C24—H24C | 109.5 |
C7—C8—C9 | 117.6 (3) | C1S—O1S—H1S | 99.6 |
C7—C8—C12 | 121.7 (3) | H1W—O1W—H2W | 130.3 |
C9—C8—C12 | 120.8 (3) | O1S—C1S—C2S | 112.2 (4) |
C10—C9—C8 | 119.4 (3) | O1S—C1S—H1SA | 109.2 |
C10—C9—H9A | 120.3 | C2S—C1S—H1SA | 109.2 |
C8—C9—H9A | 120.3 | O1S—C1S—H1SB | 109.2 |
N2—C10—C9 | 123.4 (3) | C2S—C1S—H1SB | 109.2 |
N2—C10—H10A | 118.3 | H1SA—C1S—H1SB | 107.9 |
C9—C10—H10A | 118.3 | C1S—C2S—H2SA | 109.5 |
C3—C11—H11A | 109.5 | C1S—C2S—H2SB | 109.5 |
C3—C11—H11B | 109.5 | H2SA—C2S—H2SB | 109.5 |
H11A—C11—H11B | 109.5 | C1S—C2S—H2SC | 109.5 |
C3—C11—H11C | 109.5 | H2SA—C2S—H2SC | 109.5 |
H11A—C11—H11C | 109.5 | H2SB—C2S—H2SC | 109.5 |
H11B—C11—H11C | 109.5 | ||
O1—V1—N1—C1 | −8.2 (3) | V1—N1—C5—C6 | −2.2 (3) |
N4—V1—N1—C1 | −162.1 (3) | C3—C4—C5—N1 | 1.1 (5) |
N3—V1—N1—C1 | −102.5 (2) | C3—C4—C5—C6 | −178.7 (3) |
N2—V1—N1—C1 | 178.9 (3) | C10—N2—C6—C7 | −0.9 (4) |
Cl1—V1—N1—C1 | 91.0 (2) | V1—N2—C6—C7 | 175.3 (2) |
O1—V1—N1—C5 | 173.1 (2) | C10—N2—C6—C5 | −180.0 (3) |
N4—V1—N1—C5 | 19.2 (4) | V1—N2—C6—C5 | −3.8 (3) |
N3—V1—N1—C5 | 78.8 (2) | N1—C5—C6—N2 | 4.0 (4) |
N2—V1—N1—C5 | 0.2 (2) | C4—C5—C6—N2 | −176.2 (3) |
Cl1—V1—N1—C5 | −87.8 (2) | N1—C5—C6—C7 | −175.2 (3) |
O1—V1—N2—C10 | 147.3 (4) | C4—C5—C6—C7 | 4.7 (5) |
N4—V1—N2—C10 | 4.0 (3) | N2—C6—C7—C8 | 0.5 (5) |
N1—V1—N2—C10 | 177.8 (3) | C5—C6—C7—C8 | 179.6 (3) |
N3—V1—N2—C10 | 81.3 (3) | C6—C7—C8—C9 | 0.0 (5) |
Cl1—V1—N2—C10 | −88.8 (2) | C6—C7—C8—C12 | −179.9 (3) |
O1—V1—N2—C6 | −28.5 (5) | C7—C8—C9—C10 | −0.1 (5) |
N4—V1—N2—C6 | −171.8 (2) | C12—C8—C9—C10 | 179.8 (3) |
N1—V1—N2—C6 | 2.1 (2) | C6—N2—C10—C9 | 0.7 (4) |
N3—V1—N2—C6 | −94.4 (2) | V1—N2—C10—C9 | −175.0 (2) |
Cl1—V1—N2—C6 | 95.5 (2) | C8—C9—C10—N2 | −0.3 (5) |
O1—V1—N4—C22 | 90.6 (3) | C17—N3—C13—C14 | −2.0 (5) |
N1—V1—N4—C22 | −116.2 (3) | V1—N3—C13—C14 | 171.4 (2) |
N3—V1—N4—C22 | −178.1 (3) | N3—C13—C14—C15 | 0.0 (5) |
N2—V1—N4—C22 | −98.0 (3) | C13—C14—C15—C16 | 2.2 (5) |
Cl1—V1—N4—C22 | −9.1 (3) | C13—C14—C15—C23 | −177.7 (3) |
O1—V1—N4—C18 | −86.5 (2) | C14—C15—C16—C17 | −2.3 (5) |
N1—V1—N4—C18 | 66.7 (4) | C23—C15—C16—C17 | 177.6 (3) |
N3—V1—N4—C18 | 4.8 (2) | C13—N3—C17—C16 | 1.8 (4) |
N2—V1—N4—C18 | 84.9 (2) | V1—N3—C17—C16 | −172.3 (2) |
Cl1—V1—N4—C18 | 173.8 (2) | C13—N3—C17—C18 | −178.8 (3) |
O1—V1—N3—C13 | −77.9 (3) | V1—N3—C17—C18 | 7.1 (3) |
N4—V1—N3—C13 | 180.0 (3) | C15—C16—C17—N3 | 0.4 (5) |
N1—V1—N3—C13 | 16.9 (3) | C15—C16—C17—C18 | −179.0 (3) |
N2—V1—N3—C13 | 89.3 (3) | C22—N4—C18—C19 | 1.1 (4) |
Cl1—V1—N3—C13 | 131.5 (3) | V1—N4—C18—C19 | 178.4 (2) |
O1—V1—N3—C17 | 95.7 (2) | C22—N4—C18—C17 | −179.9 (3) |
N4—V1—N3—C17 | −6.5 (2) | V1—N4—C18—C17 | −2.6 (3) |
N1—V1—N3—C17 | −169.5 (2) | N3—C17—C18—N4 | −3.0 (4) |
N2—V1—N3—C17 | −97.2 (2) | C16—C17—C18—N4 | 176.4 (3) |
Cl1—V1—N3—C17 | −54.9 (4) | N3—C17—C18—C19 | 175.9 (3) |
C5—N1—C1—C2 | −0.4 (5) | C16—C17—C18—C19 | −4.7 (5) |
V1—N1—C1—C2 | −179.1 (2) | N4—C18—C19—C20 | −1.1 (5) |
N1—C1—C2—C3 | 1.2 (5) | C17—C18—C19—C20 | −179.9 (3) |
C1—C2—C3—C4 | −0.9 (5) | C18—C19—C20—C21 | 0.3 (5) |
C1—C2—C3—C11 | 179.9 (3) | C18—C19—C20—C24 | 179.7 (3) |
C2—C3—C4—C5 | −0.3 (5) | C19—C20—C21—C22 | 0.4 (5) |
C11—C3—C4—C5 | 178.9 (3) | C24—C20—C21—C22 | −179.1 (3) |
C1—N1—C5—C4 | −0.8 (4) | C18—N4—C22—C21 | −0.4 (5) |
V1—N1—C5—C4 | 177.9 (2) | V1—N4—C22—C21 | −177.5 (2) |
C1—N1—C5—C6 | 179.0 (3) | C20—C21—C22—N4 | −0.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1S—H1S···Cl2 | 0.93 | 2.24 | 3.128 (3) | 159 |
O1W—H1W···Cl2i | 0.84 | 2.45 | 3.221 (3) | 152 |
O1W—H2W···Cl2ii | 0.92 | 2.37 | 3.284 (3) | 171 |
C1—H1B···O1 | 0.95 | 2.51 | 2.999 (4) | 112 |
C2—H2A···O1Siii | 0.95 | 2.41 | 3.301 (4) | 155 |
C4—H4A···Cl1iv | 0.95 | 2.76 | 3.670 (4) | 160 |
C7—H7A···Cl1iv | 0.95 | 2.77 | 3.626 (3) | 151 |
C9—H9A···Cl2ii | 0.95 | 2.63 | 3.561 (4) | 165 |
C13—H13A···O1Siv | 0.95 | 2.59 | 3.284 (4) | 130 |
C14—H14A···Cl2iv | 0.95 | 2.62 | 3.558 (3) | 170 |
C19—H19A···O1v | 0.95 | 2.52 | 3.229 (4) | 132 |
C21—H21A···O1Wvi | 0.95 | 2.45 | 3.315 (5) | 151 |
C22—H22A···Cl1 | 0.95 | 2.64 | 3.262 (3) | 123 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+2; (vi) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [VClO(C12H12N2)2]Cl·C2H6O·H2O |
Mr | 570.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 9.6955 (11), 10.9905 (12), 14.5739 (17) |
α, β, γ (°) | 68.711 (2), 72.401 (2), 81.381 (2) |
V (Å3) | 1377.9 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.32 × 0.14 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.926, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12257, 5363, 4398 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.144, 1.00 |
No. of reflections | 5363 |
No. of parameters | 330 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.09, −0.89 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1S—H1S···Cl2 | 0.93 | 2.24 | 3.128 (3) | 159 |
O1W—H1W···Cl2i | 0.84 | 2.45 | 3.221 (3) | 152 |
O1W—H2W···Cl2ii | 0.92 | 2.37 | 3.284 (3) | 171 |
C1—H1B···O1 | 0.95 | 2.51 | 2.999 (4) | 112 |
C2—H2A···O1Siii | 0.95 | 2.41 | 3.301 (4) | 155 |
C4—H4A···Cl1iv | 0.95 | 2.76 | 3.670 (4) | 160 |
C7—H7A···Cl1iv | 0.95 | 2.77 | 3.626 (3) | 151 |
C9—H9A···Cl2ii | 0.95 | 2.63 | 3.561 (4) | 165 |
C13—H13A···O1Siv | 0.95 | 2.59 | 3.284 (4) | 130 |
C14—H14A···Cl2iv | 0.95 | 2.62 | 3.558 (3) | 170 |
C19—H19A···O1v | 0.95 | 2.52 | 3.229 (4) | 132 |
C21—H21A···O1Wvi | 0.95 | 2.45 | 3.315 (5) | 151 |
C22—H22A···Cl1 | 0.95 | 2.64 | 3.262 (3) | 123 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+2; (vi) −x, −y, −z+2. |
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 synthesis and crystal structures of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012b), and [CdBr2(4,4'-dmbipy)(DMSO)], (III) (Shirvan & Haydari Dezfuli, 2012a) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 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], (IV) (Yousefi et al., 2008), [Hg(4,4'-dmbipy)Br2], (V) (Kalateh et al., 2008), [Fe(4,4'-dmbipy)Cl3(DMSO)], (VI) (Amani et al., 2009), [Pt(4,4'-dmbipy)Cl4], (VII) (Hojjat Kashani et al., 2008), [Cd(4,4'-dmbipy)I2(DMSO)], (VIII) (Kalateh et al., 2010), [Zn(4,4'-dmbipy)Br2], (IX) (Alizadeh et al., 2010), [Zn(4,4'-dmbipy)(H2O)(NO3)2], (X) (Shirvan & Haydari Dezfuli, 2011) and [In(4,4'-dmbpy)Cl3(DMSO)], (XI) (Ahmadi et al., 2008). We report herein the synthesis and crystal structure of the title compound, (I).
In the title compound (Fig. 1), the VIV atom is six-coordinated in a distorted octahedral geometry by four N atoms from two 4,4'-dmbipy ligands, one O atom and one Cl atom. There are also one ethanol and one water solvent molecules in the asymmetric unit. The V—Cl, V—N and V—O bond lengths and angles are in good agreement with the corresponding values in [VOCl(dtbipy)Cl]Cl.CH2Cl2 (Triantafillou et al., 2004) (dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine).
In the crystal, intermolecular O—H···Cl, C—H···O and C—H···Cl hydrogen bonds, intramolecular C—H···O and C—H···Cl hydrogen bonds (Table 1) and π–π contacts between the pyridine rings (Fig. 2), Cg3···Cg4i and Cg5···Cg6ii, with centroid–centroid distances of 3.7236 (17) and 3.6026 (19) Å [symmetry codes: (i) 1-x, 1-y, 1-z; (ii) -x, 1-y, 2-z. Cg3, Cg4, Cg5 and Cg6 are the centroids of the N1/C1–C5, N2/C6–C10, N3/C13–C17 and N4/C18–C22 rings, respectively], stabilize the structure.