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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages m25-m26

Di-μ-oxido-bis­­({2-[(R,R)-(−)-(2-amino­cyclo­hexyl)imino­meth­yl]-4-nitro­phenolato-κ3N,N′,O}oxidovanadium(V)) di­methyl sulfoxide disolvate

aUniversity of Gdańsk, Faculty of Chemistry, Sobieskiego 18/19, 80-952 Gdańsk, Poland
*Correspondence e-mail: greg@chem.univ.gda.pl

(Received 30 October 2008; accepted 19 November 2008; online 10 December 2008)

The title compound, [V2(C13H16N3O3)2O4]·2C2H6OS, is a centrosymmetric dimeric complex solvated by two dimethyl sulfoxide mol­ecules. Each VV atom is six-coordinated by one oxide group, two N atoms and one O atom from the tridentate Schiff base ligand, and by two additional bridging O atoms in a distorted octa­hedral coordination geometry. Three atoms of the cyclo­hexane ring are each disordered over two sites, with occupancy factors of 0.501 (10) and 0.499 (10). C—H⋯O and N—H⋯O hydrogen bonds link the dimers and solvent mol­ecules into a supra­molecular network.

Related literature

For general background, see: Carter-Franklin et al. (2003[Carter-Franklin, J. N., Parrish, J. D., Tchirret-Guth, R. A., Little, R. D. & Butler, A. (2003). J. Am. Chem. Soc. 125, 3688-3689.]); Eady (2003[Eady, R. R. (2003). Coord. Chem. Rev. 237, 23-30.]); Evangelou (2002[Evangelou, A. M. (2002). Crit. Rev. Oncol. Hematol. 42, 249-265.]); Mendz (1991[Mendz, G. L. (1991). Arch. Biochem. Biophys. 291, 201-211.]); Parekh et al. (2006[Parekh, H. M., Panchal, P. K. & Patel, M. N. (2006). Pharm. Chem. J. Chem. 40, 494-497.]); Rao et al. (1981[Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.]); Rehder et al. (2002[Rehder, D., Costa Pessoa, J., Geraldes, C. F. G. C., Castro, M. M. C. A., Kabanos, T., Kiss, T., Meier, B., Micera, G., Pettersson, L., Rangel, M., Salifoglou, A., Turel, I. & Wang, D. (2002). J. Biol. Inorg. Chem. 7, 384-396.], 2003[Rehder, D., Antoni, G., Licini, G. M., Schulzke, C. & Meier, B. (2003). Coord. Chem. Rev. 237, 53-63.]); Shahzadi et al. (2007[Shahzadi, S., Ali, S., Parvez, M., Badshah, A., Ahmed, E. & Malik, A. (2007). Russ. J. Inorg. Chem. 52, 386-393.]). For related structures, see: Kwiatkowski et al. (2007[Kwiatkowski, E., Romanowski, G., Nowicki, W., Kwiatkowski, M. & Suwińska, K. (2007). Polyhedron, 26, 2559-2568.]); Mokry & Carrano (1993[Mokry, L. M. & Carrano, C. J. (1993). Inorg. Chem. 32, 6119-6121.]); Romanowski et al. (2008[Romanowski, G., Kwiatkowski, E., Nowicki, W., Kwiatkowski, M. & Lis, T. (2008). Polyhedron, 27, 1601-1609.]); Root et al. (1993[Root, C. A., Hoeschele, J. D., Cornman, C. R., Kampf, J. W. & Pecoraro, V. L. (1993). Inorg. Chem. 32, 3855-3861.]). For the synthesis, see: Kwiatkowski et al. (2003[Kwiatkowski, E., Romanowski, G., Nowicki, W., Kwiatkowski, M. & Suwińska, K. (2003). Polyhedron, 22, 1009-1018.]).

[Scheme 1]

Experimental

Crystal data
  • [V2(C13H16N3O3)2O4]·2C2H6OS

  • Mr = 846.71

  • Triclinic, [P \overline 1]

  • a = 7.249 (1) Å

  • b = 11.747 (2) Å

  • c = 11.809 (2) Å

  • α = 77.69 (3)°

  • β = 88.62 (3)°

  • γ = 76.13 (3)°

  • V = 953.4 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.67 mm−1

  • T = 295 (2) K

  • 0.60 × 0.25 × 0.10 mm

Data collection
  • Oxford Diffraction Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.720, Tmax = 0.936

  • 6786 measured reflections

  • 3355 independent reflections

  • 3245 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.194

  • S = 1.44

  • 3355 reflections

  • 256 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Selected bond lengths (Å)

N11—V19 2.186 (5)
N18—V19 2.109 (5)
V19—O20 1.610 (4)
V19—O21i 1.663 (4)
V19—O22 1.929 (4)
V19—O21 2.372 (4)
Symmetry code: (i) -x, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N18—H18A⋯O22i 0.90 2.29 3.069 (6) 145
N18—H18B⋯O26ii 0.90 2.16 2.913 (8) 140
C5—H5A⋯O26iii 0.93 2.57 3.494 (9) 171
C10—H10A⋯O21iv 0.93 2.49 3.167 (7) 130
C13—H13B⋯O21iv 0.97 2.55 3.392 (7) 145
C14—H14A⋯O26v 0.97 2.38 3.211 (11) 144
C15—H15B⋯O8vi 0.97 2.32 3.109 (17) 138
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x, -y+1, -z+1; (iii) -x, -y+2, -z+1; (iv) -x+1, -y+1, -z+2; (v) -x+1, -y+1, -z+1; (vi) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Research in vanadium chemistry and biochemistry increased after discovery of insulin mimetic (Rehder et al., 2002), anticancer (Evangelou, 2002), antifungal and antibacterial (Parekh et al., 2006; Shahzadi et al., 2007) activity of this element. Oxidovanadium(IV) and (V) compounds exert catalytic activity like some biological enzymes, viz. haloperoxidases (Carter-Franklin et al., 2003; Rehder et al., 2003), phosphomutases (Mendz, 1991) and nitrogenases (Eady, 2003). Moreover, investigation of vanadium(V) complexes with Schiff bases is prompted by the fact that these ligands are coordinated to the metal through O and N atoms, similar to the coordination environments of natural systems.

The title compound was earlier characterized by spectroscopic methods (IR, UV-Vis, 1H and 51V NMR) (Kwiatkowski et al., 2007). The crystal structure consists of a centrosymmetric dimeric vanadium(V) complex and two dimethyl sulfoxide (DMSO) molecules (Fig. 1). The singly deprotonated Schiff base acts as a tridentate ligand, forming one five- and one six-membered chelate rings. Each VV atom is six-coordinated in a distorted octahedral environment. Two axial positions are occupied by one phenolate O atom (O22) and one amine N atom (N18), and the equatorial positions are occupied by one azomethine N atom (N11), two strongly [O20i and O21i; symmetry code: (i) -x, -y + 1, -z + 2] and one weakly (O21) bonded oxide groups (Fig. 1). The V19—O20, V19—O21i(bridging) and V19—O22(phenolate) bond distances (Table 1) agree well with the corresponding values reported for related compounds (Mokry & Carrano, 1993; Romanowski et al., 2008; Root et al., 1993). The V19—O21 bond is longer than O21—V19i bond due to the involvement of this O atom in bridging between the V atoms. The V19, O21, V19i, O21i atoms are situated in the vertices of a parallelogram with the acute O21—V19—O21i angle of 77.9 (2)°. The V···V separation is 3.170 (1)Å and falls within the range of known V···V distances in double-bridged vanadium polynuclear systems (Mokry & Carrano, 1993; Romanowski et al., 2008; Root et al., 1993). Three C atoms of the cyclohexane ring exhibit twofold disorder. The C12, C15 and C17 atoms are each disordered over two sites, with occupancy factors of 0.501 (10) and 0.499 (10). The five-membered chelate ring defined by V19, N11, C12, C17, N18 adopts a twisted conformation on C12 and C17 atoms, with P = 250.3 (5)° and τ(M) = 56.7 (6)° for reference bond V19—N11 (Rao et al., 1981) (Fig. 1).

In the crystal structure, C—H···O and N—H···O hydrogen bonds link the dimers and solvent molecules into a supramolecular network (Table 2; Fig. 2).

Related literature top

For general background, see: Carter-Franklin et al. (2003); Eady (2003); Evangelou (2002); Mendz (1991); Parekh et al. (2006); Rao et al. (1981); Rehder et al. (2002, 2003); Shahzadi et al. (2007). For related structures, see: Kwiatkowski et al. (2007); Mokry & Carrano (1993); Romanowski et al. (2008); Root et al. (1993). For the synthesis, see: Kwiatkowski et al. (2003).

Experimental top

The title compound was obtained in a template/complexation reaction analogous to that described for preparation of dioxidovanadium(V) complexes with Schiff base ligands (Kwiatkowski et al., 2003). A solution of R,R-(–)-1,2-diaminocyclohexane (1 mmol) in absolute ethanol (10 ml) was added under stirring to a freshly filtered solution of vanadium(V) oxytriethoxide (1 mmol) in absolute ethanol (50 ml), producing a yellow suspension of the intermediate. 5-Nitrosalicylaldehyde (1 mmol) dissolved in absolute ethanol was added to the aforementioned suspension. After refluxing of the resulting mixture (70 ml) for 2 h and its cooling to room temperature, the separated solids were filtered off, washed several times with ethanol, recrystallized from DMSO–EtOH mixture and dried over molecular sieves.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 and N—H = 0.90 Å, and with Uiso(H) = 1.2(1.5 for methyl group)Ueq(C,N).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 25% probability level. Disordered parts are shown by open bonds. [Symmetry code: (i) -x, -y + 1, -z + 2.]
[Figure 2] Fig. 2. The arrangement of molecules in the title compound, viewed approximately along the a axis. Hydrogen bonds are represented by dashed lines.
Di-µ-oxido-bis({2-[(R,R)-(-)-(2-aminocyclohexyl)iminomethyl]- 4-nitrophenolato-κ3N,N',O}oxidovanadium(V)) dimethyl sulfoxide disolvate top
Crystal data top
[V2(C13H16N3O3)2O4]·2C2H6OSZ = 1
Mr = 846.71F(000) = 440
Triclinic, P1Dx = 1.475 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.249 (1) ÅCell parameters from 3355 reflections
b = 11.747 (2) Åθ = 3.0–25.1°
c = 11.809 (2) ŵ = 0.67 mm1
α = 77.69 (3)°T = 295 K
β = 88.62 (3)°Needle, yellow
γ = 76.13 (3)°0.60 × 0.25 × 0.10 mm
V = 953.4 (3) Å3
Data collection top
Oxford Diffraction Ruby CCD
diffractometer
3355 independent reflections
Radiation source: Enhance (Mo) X-ray Source3245 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 10.4002 pixels mm-1θmax = 25.1°, θmin = 3.0°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
k = 1311
Tmin = 0.720, Tmax = 0.936l = 1314
6786 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.194 w = 1/[σ2(Fo2) + (0.0232P)2 + 4.2049P]
where P = (Fo2 + 2Fc2)/3
S = 1.44(Δ/σ)max < 0.001
3355 reflectionsΔρmax = 0.53 e Å3
256 parametersΔρmin = 0.44 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (16)
Crystal data top
[V2(C13H16N3O3)2O4]·2C2H6OSγ = 76.13 (3)°
Mr = 846.71V = 953.4 (3) Å3
Triclinic, P1Z = 1
a = 7.249 (1) ÅMo Kα radiation
b = 11.747 (2) ŵ = 0.67 mm1
c = 11.809 (2) ÅT = 295 K
α = 77.69 (3)°0.60 × 0.25 × 0.10 mm
β = 88.62 (3)°
Data collection top
Oxford Diffraction Ruby CCD
diffractometer
3355 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
3245 reflections with I > 2σ(I)
Tmin = 0.720, Tmax = 0.936Rint = 0.021
6786 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0790 restraints
wR(F2) = 0.194H-atom parameters constrained
S = 1.44Δρmax = 0.53 e Å3
3355 reflectionsΔρmin = 0.44 e Å3
256 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1768 (8)0.7547 (5)0.8238 (5)0.0318 (12)
C20.3625 (8)0.7030 (5)0.7934 (5)0.0322 (12)
C30.4761 (10)0.7777 (6)0.7378 (6)0.0448 (15)
H3A0.59990.74500.71880.054*
C40.4032 (11)0.8999 (6)0.7112 (6)0.0505 (17)
C50.2207 (11)0.9522 (6)0.7375 (6)0.0525 (18)
H5A0.17271.03480.71550.063*
C60.1108 (10)0.8802 (5)0.7969 (5)0.0403 (14)
H6A0.00950.91510.81970.048*
N70.5242 (12)0.9771 (6)0.6526 (7)0.077 (2)
O80.4474 (11)1.0817 (5)0.6099 (7)0.103 (3)
O90.6933 (10)0.9331 (6)0.6482 (8)0.101 (3)
C100.4411 (8)0.5748 (5)0.8148 (5)0.0335 (13)
H10A0.57130.54730.80710.040*
N110.3421 (7)0.4965 (4)0.8437 (4)0.0329 (11)
C120.436 (2)0.3677 (13)0.8877 (13)0.030 (3)0.501 (10)
H12A0.42630.34960.97220.036*0.501 (10)
C12A0.428 (2)0.3682 (13)0.8308 (15)0.032 (3)0.499 (10)
H12B0.40400.36140.75150.038*0.499 (10)
C130.6421 (8)0.3255 (5)0.8594 (6)0.0405 (14)
H13A0.66070.36290.77980.049*
H13B0.72020.35220.90900.049*
C140.7089 (11)0.1916 (6)0.8742 (9)0.070 (2)
H14A0.82510.17490.83180.083*
H14B0.74150.15790.95570.083*
C150.5840 (19)0.1297 (11)0.8390 (14)0.048 (4)0.501 (10)
H15A0.63530.04410.86560.058*0.501 (10)
H15B0.57540.14700.75500.058*0.501 (10)
C15A0.595 (2)0.1146 (13)0.9356 (14)0.054 (4)*0.499 (10)
H15C0.60120.11261.01800.064*0.499 (10)
H15D0.64330.03350.92400.064*0.499 (10)
C160.3804 (10)0.1654 (6)0.8875 (8)0.057 (2)
H16A0.38520.14850.97150.069*
H16B0.29720.12160.86210.069*
C170.3085 (16)0.3038 (10)0.8368 (11)0.032 (3)0.501 (10)
H17A0.30970.32190.75190.038*0.501 (10)
C17A0.3189 (16)0.2942 (10)0.9138 (13)0.033 (3)*0.499 (10)
H17B0.34530.29410.99480.040*0.499 (10)
N180.1126 (7)0.3474 (4)0.8793 (4)0.0361 (11)
H18A0.10720.31080.95410.043*
H18B0.02800.32640.83820.043*
V190.03456 (13)0.53484 (9)0.86534 (8)0.0289 (3)
O200.0303 (7)0.5634 (4)0.7308 (4)0.0490 (12)
O210.1601 (5)0.4698 (4)1.0582 (3)0.0325 (9)
O220.0653 (6)0.6894 (3)0.8812 (3)0.0364 (9)
S230.0005 (3)0.6916 (2)0.44455 (18)0.0657 (6)
C240.0490 (17)0.8021 (9)0.5086 (8)0.094 (3)
H24A0.02720.87910.47110.140*
H24B0.18110.80190.50060.140*
H24C0.02020.78600.58940.140*
C250.2180 (17)0.5849 (10)0.4774 (10)0.104 (4)
H25A0.23510.53090.42530.156*
H25B0.21820.54040.55570.156*
H25C0.31970.62520.46930.156*
O260.0092 (10)0.7404 (5)0.3172 (5)0.0747 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (3)0.034 (3)0.028 (3)0.015 (2)0.004 (2)0.008 (2)
C20.040 (3)0.033 (3)0.027 (3)0.016 (2)0.003 (2)0.006 (2)
C30.045 (4)0.040 (4)0.053 (4)0.019 (3)0.003 (3)0.009 (3)
C40.065 (5)0.036 (3)0.055 (4)0.024 (3)0.014 (3)0.006 (3)
C50.066 (5)0.033 (3)0.057 (4)0.013 (3)0.004 (4)0.006 (3)
C60.051 (4)0.033 (3)0.038 (3)0.011 (3)0.002 (3)0.008 (3)
N70.081 (5)0.046 (4)0.109 (6)0.033 (4)0.030 (5)0.011 (4)
O80.115 (6)0.048 (4)0.140 (7)0.034 (4)0.046 (5)0.007 (4)
O90.081 (5)0.072 (4)0.156 (7)0.041 (4)0.047 (5)0.016 (4)
C100.029 (3)0.038 (3)0.034 (3)0.012 (2)0.002 (2)0.007 (2)
N110.031 (2)0.028 (2)0.040 (3)0.011 (2)0.003 (2)0.003 (2)
C120.035 (7)0.030 (7)0.026 (8)0.010 (5)0.002 (7)0.008 (7)
C12A0.031 (7)0.033 (7)0.034 (9)0.008 (5)0.003 (7)0.011 (7)
C130.034 (3)0.038 (3)0.050 (4)0.011 (3)0.003 (3)0.008 (3)
C140.040 (4)0.040 (4)0.121 (8)0.002 (3)0.001 (4)0.008 (4)
C150.053 (8)0.028 (6)0.064 (10)0.003 (6)0.013 (7)0.023 (6)
C160.050 (4)0.036 (4)0.093 (6)0.017 (3)0.004 (4)0.021 (4)
C170.039 (6)0.032 (6)0.027 (7)0.010 (5)0.001 (5)0.013 (5)
N180.032 (3)0.042 (3)0.039 (3)0.015 (2)0.001 (2)0.009 (2)
V190.0284 (5)0.0349 (6)0.0256 (5)0.0116 (4)0.0012 (4)0.0062 (4)
O200.061 (3)0.053 (3)0.028 (2)0.007 (2)0.009 (2)0.005 (2)
O210.029 (2)0.041 (2)0.031 (2)0.0135 (17)0.0036 (16)0.0099 (17)
O220.042 (2)0.033 (2)0.037 (2)0.0149 (18)0.0058 (18)0.0062 (17)
S230.0761 (14)0.0722 (14)0.0477 (11)0.0224 (11)0.0021 (10)0.0052 (10)
C240.125 (9)0.093 (7)0.062 (6)0.005 (6)0.013 (6)0.038 (5)
C250.121 (10)0.086 (7)0.080 (7)0.006 (7)0.012 (7)0.003 (6)
O260.114 (5)0.066 (4)0.043 (3)0.014 (3)0.001 (3)0.020 (3)
Geometric parameters (Å, º) top
C1—O221.323 (7)C15—C161.564 (16)
C1—C61.405 (8)C15—H15A0.9700
C1—C21.410 (8)C15—H15B0.9700
C2—C31.397 (8)C15A—C161.599 (16)
C2—C101.446 (8)C15A—H15C0.9700
C3—C41.375 (9)C15A—H15D0.9700
C3—H3A0.9300C16—C17A1.567 (13)
C4—C51.377 (10)C16—C171.570 (13)
C4—N71.468 (9)C16—H16A0.9700
C5—C61.373 (9)C16—H16B0.9700
C5—H5A0.9300C17—N181.503 (12)
C6—H6A0.9300C17—H17A0.9800
N7—O91.215 (10)C17A—N181.505 (12)
N7—O81.222 (9)C17A—H17B0.9800
C10—N111.284 (7)N18—V192.109 (5)
C10—H10A0.9300N18—H18A0.9000
N11—C121.487 (15)N18—H18B0.9000
N11—C12A1.526 (15)V19—O201.610 (4)
N11—V192.186 (5)V19—O21i1.663 (4)
C12—C131.507 (16)V19—O221.929 (4)
C12—C171.529 (18)V19—O212.372 (4)
C12—H12A0.9800O21—V19i1.663 (4)
C12A—C17A1.51 (2)S23—O261.489 (6)
C12A—C131.534 (16)S23—C241.744 (10)
C12A—H12B0.9800S23—C251.761 (11)
C13—C141.503 (9)C24—H24A0.9600
C13—H13A0.9700C24—H24B0.9600
C13—H13B0.9700C24—H24C0.9600
C14—C151.409 (15)C25—H25A0.9600
C14—C15A1.439 (16)C25—H25B0.9600
C14—H14A0.9700C25—H25C0.9600
C14—H14B0.9700
O22—C1—C6118.8 (5)C14—C15A—H15D110.0
O22—C1—C2122.3 (5)C16—C15A—H15D110.0
C6—C1—C2118.9 (5)H15C—C15A—H15D108.3
C3—C2—C1119.3 (5)C15—C16—C17A116.3 (7)
C3—C2—C10117.8 (6)C15—C16—C17105.1 (8)
C1—C2—C10122.9 (5)C17A—C16—C15A104.9 (9)
C4—C3—C2119.5 (6)C17—C16—C15A118.5 (8)
C4—C3—H3A120.3C15—C16—H16A110.7
C2—C3—H3A120.3C17A—C16—H16A77.7
C3—C4—C5122.2 (6)C17—C16—H16A110.7
C3—C4—N7118.8 (7)C15A—C16—H16A69.4
C5—C4—N7119.0 (6)C15—C16—H16B110.7
C6—C5—C4118.8 (6)C17A—C16—H16B126.2
C6—C5—H5A120.6C17—C16—H16B110.7
C4—C5—H5A120.6C15A—C16—H16B127.8
C5—C6—C1121.1 (6)H16A—C16—H16B108.8
C5—C6—H6A119.4N18—C17—C12106.1 (9)
C1—C6—H6A119.4N18—C17—C16109.3 (8)
O9—N7—O8124.1 (7)C12—C17—C16107.9 (9)
O9—N7—C4118.3 (7)N18—C17—H17A111.1
O8—N7—C4117.6 (8)C12—C17—H17A111.1
N11—C10—C2124.0 (5)C16—C17—H17A111.1
N11—C10—H10A118.0N18—C17A—C12A105.7 (10)
C2—C10—H10A118.0N18—C17A—C16109.3 (8)
C10—N11—C12120.6 (7)C12A—C17A—C16104.9 (10)
C10—N11—C12A118.6 (7)N18—C17A—H17B112.2
C10—N11—V19125.9 (4)C12A—C17A—H17B112.2
C12—N11—V19112.6 (6)C16—C17A—H17B112.2
C12A—N11—V19113.3 (6)C17—N18—V19113.2 (5)
N11—C12—C13117.7 (10)C17A—N18—V19112.5 (5)
N11—C12—C17102.5 (10)C17—N18—H18A108.9
C13—C12—C17112.1 (11)C17A—N18—H18A77.3
N11—C12—H12A108.1V19—N18—H18A108.9
C13—C12—H12A108.1C17—N18—H18B108.9
C17—C12—H12A108.1C17A—N18—H18B133.8
C17A—C12A—N11103.9 (11)V19—N18—H18B108.9
C17A—C12A—C13110.9 (11)H18A—N18—H18B107.8
N11—C12A—C13113.7 (10)O20—V19—O21i106.7 (2)
C17A—C12A—H12B109.4O20—V19—O22101.0 (2)
N11—C12A—H12B109.4O21i—V19—O2299.26 (19)
C13—C12A—H12B109.4O20—V19—N1894.0 (2)
C14—C13—C12113.9 (7)O21i—V19—N1893.45 (19)
C14—C13—C12A111.2 (7)O22—V19—N18156.55 (19)
C14—C13—H13A108.8O20—V19—N1198.4 (2)
C12—C13—H13A108.8O21i—V19—N11153.60 (19)
C12A—C13—H13A86.8O22—V19—N1183.61 (18)
C14—C13—H13B108.8N18—V19—N1176.42 (18)
C12—C13—H13B108.8O20—V19—O21172.2 (2)
C12A—C13—H13B129.9O21i—V19—O2177.86 (17)
H13A—C13—H13B107.7O22—V19—O2184.18 (16)
C15—C14—C15A46.2 (9)N18—V19—O2179.31 (17)
C15—C14—C13118.0 (8)N11—V19—O2176.33 (16)
C15A—C14—C13120.1 (9)V19i—O21—V19102.14 (17)
C15—C14—H14A107.8C1—O22—V19129.1 (4)
C15A—C14—H14A131.9O26—S23—C24106.2 (4)
C13—C14—H14A107.8O26—S23—C25107.2 (5)
C15—C14—H14B107.8C24—S23—C2598.3 (6)
C15A—C14—H14B63.4S23—C24—H24A109.5
C13—C14—H14B107.8S23—C24—H24B109.5
H14A—C14—H14B107.2H24A—C24—H24B109.5
C14—C15—C16112.3 (9)S23—C24—H24C109.5
C14—C15—H15A109.1H24A—C24—H24C109.5
C16—C15—H15A109.1H24B—C24—H24C109.5
C14—C15—H15B109.1S23—C25—H25A109.5
C16—C15—H15B109.1S23—C25—H25B109.5
H15A—C15—H15B107.9H25A—C25—H25B109.5
C14—C15A—C16108.7 (10)S23—C25—H25C109.5
C14—C15A—H15C110.0H25A—C25—H25C109.5
C16—C15A—H15C110.0H25B—C25—H25C109.5
O22—C1—C2—C3176.9 (5)C15—C16—C17—N18179.6 (8)
C6—C1—C2—C30.2 (8)C17A—C16—C17—N1864.4 (11)
O22—C1—C2—C104.5 (8)C15A—C16—C17—N18137.2 (10)
C6—C1—C2—C10178.4 (5)C15—C16—C17—C1264.7 (12)
C1—C2—C3—C41.6 (9)C17A—C16—C17—C1250.5 (11)
C10—C2—C3—C4177.1 (6)C15A—C16—C17—C1222.3 (14)
C2—C3—C4—C50.1 (11)N11—C12A—C17A—N1855.5 (12)
C2—C3—C4—N7179.9 (7)C13—C12A—C17A—N18178.1 (9)
C3—C4—C5—C63.0 (12)N11—C12A—C17A—C16170.9 (9)
N7—C4—C5—C6177.2 (7)C13—C12A—C17A—C1666.5 (13)
C4—C5—C6—C14.4 (11)C15—C16—C17A—N18141.3 (9)
O22—C1—C6—C5180.0 (6)C17—C16—C17A—N1864.3 (12)
C2—C1—C6—C52.8 (9)C15A—C16—C17A—N18176.0 (9)
C3—C4—N7—O913.0 (13)C15—C16—C17A—C12A28.3 (14)
C5—C4—N7—O9167.2 (9)C17—C16—C17A—C12A48.7 (12)
C3—C4—N7—O8166.1 (8)C15A—C16—C17A—C12A71.0 (12)
C5—C4—N7—O813.7 (13)C12—C17—N18—C17A51.4 (11)
C3—C2—C10—N11165.8 (6)C16—C17—N18—C17A64.7 (11)
C1—C2—C10—N1112.8 (9)C12—C17—N18—V1945.1 (10)
C2—C10—N11—C12167.3 (8)C16—C17—N18—V19161.1 (6)
C2—C10—N11—C12A163.0 (8)C12A—C17A—N18—C1747.5 (11)
C2—C10—N11—V191.0 (8)C16—C17A—N18—C1764.9 (12)
C10—N11—C12—C1320.5 (15)C12A—C17A—N18—V1951.1 (11)
C12A—N11—C12—C1373 (2)C16—C17A—N18—V19163.6 (6)
V19—N11—C12—C13169.7 (8)C17—N18—V19—O2082.6 (6)
C10—N11—C12—C17144.0 (8)C17A—N18—V19—O20120.2 (7)
C12A—N11—C12—C1750.9 (19)C17—N18—V19—O21i170.4 (6)
V19—N11—C12—C1746.2 (11)C17A—N18—V19—O21i132.7 (7)
C10—N11—C12A—C17A157.6 (8)C17—N18—V19—O2247.4 (8)
C12—N11—C12A—C17A56 (2)C17A—N18—V19—O229.8 (9)
V19—N11—C12A—C17A38.3 (12)C17—N18—V19—N1115.1 (6)
C10—N11—C12A—C1336.8 (14)C17A—N18—V19—N1122.6 (6)
C12—N11—C12A—C1365 (2)C17—N18—V19—O2193.4 (6)
V19—N11—C12A—C13159.0 (8)C17A—N18—V19—O2155.8 (7)
N11—C12—C13—C14162.4 (9)C10—N11—V19—O2080.1 (5)
C17—C12—C13—C1443.9 (13)C12—N11—V19—O20110.8 (7)
N11—C12—C13—C12A73 (2)C12A—N11—V19—O2082.7 (8)
C17—C12—C13—C12A45.4 (18)C10—N11—V19—O21i118.1 (6)
C17A—C12A—C13—C1449.1 (14)C12—N11—V19—O21i51.0 (9)
N11—C12A—C13—C14165.8 (9)C12A—N11—V19—O21i79.1 (9)
C17A—C12A—C13—C1252 (2)C10—N11—V19—O2220.1 (5)
N11—C12A—C13—C1264.4 (19)C12—N11—V19—O22149.0 (7)
C12—C13—C14—C1539.7 (14)C12A—N11—V19—O22177.1 (7)
C12A—C13—C14—C1512.1 (14)C10—N11—V19—N18172.2 (5)
C12—C13—C14—C15A13.6 (14)C12—N11—V19—N1818.6 (7)
C12A—C13—C14—C15A41.2 (14)C12A—N11—V19—N189.5 (7)
C15A—C14—C15—C1657.2 (12)C10—N11—V19—O21105.7 (5)
C13—C14—C15—C1648.9 (15)C12—N11—V19—O2163.5 (7)
C15—C14—C15A—C1653.4 (10)C12A—N11—V19—O2191.6 (7)
C13—C14—C15A—C1647.8 (15)O21i—V19—O21—V19i0.000 (2)
C14—C15—C16—C17A27.0 (15)O22—V19—O21—V19i100.8 (2)
C14—C15—C16—C1760.4 (13)N18—V19—O21—V19i95.9 (2)
C14—C15—C16—C15A55.7 (12)N11—V19—O21—V19i174.4 (2)
C14—C15A—C16—C1552.1 (11)C6—C1—O22—V19144.0 (4)
C14—C15A—C16—C17A60.9 (13)C2—C1—O22—V1938.9 (7)
C14—C15A—C16—C1728.2 (15)O20—V19—O22—C158.2 (5)
N11—C12—C17—N1857.2 (11)O21i—V19—O22—C1167.4 (5)
C13—C12—C17—N18175.7 (9)N18—V19—O22—C170.7 (7)
N11—C12—C17—C16174.2 (8)N11—V19—O22—C139.1 (5)
C13—C12—C17—C1658.7 (13)O21—V19—O22—C1116.0 (5)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N18—H18A···O22i0.902.293.069 (6)145
N18—H18B···O26ii0.902.162.913 (8)140
C5—H5A···O26iii0.932.573.494 (9)171
C10—H10A···O21iv0.932.493.167 (7)130
C13—H13B···O21iv0.972.553.392 (7)145
C14—H14A···O26v0.972.383.211 (11)144
C15—H15B···O8vi0.972.323.109 (17)138
Symmetry codes: (i) x, y+1, z+2; (ii) x, y+1, z+1; (iii) x, y+2, z+1; (iv) x+1, y+1, z+2; (v) x+1, y+1, z+1; (vi) x, y1, z.

Experimental details

Crystal data
Chemical formula[V2(C13H16N3O3)2O4]·2C2H6OS
Mr846.71
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.249 (1), 11.747 (2), 11.809 (2)
α, β, γ (°)77.69 (3), 88.62 (3), 76.13 (3)
V3)953.4 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.67
Crystal size (mm)0.60 × 0.25 × 0.10
Data collection
DiffractometerOxford Diffraction Ruby CCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2006)
Tmin, Tmax0.720, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
6786, 3355, 3245
Rint0.021
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.194, 1.44
No. of reflections3355
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.44

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected bond lengths (Å) top
N11—V192.186 (5)V19—O21i1.663 (4)
N18—V192.109 (5)V19—O221.929 (4)
V19—O201.610 (4)V19—O212.372 (4)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N18—H18A···O22i0.902.293.069 (6)145
N18—H18B···O26ii0.902.162.913 (8)140
C5—H5A···O26iii0.932.573.494 (9)171
C10—H10A···O21iv0.932.493.167 (7)130
C13—H13B···O21iv0.972.553.392 (7)145
C14—H14A···O26v0.972.383.211 (11)144
C15—H15B···O8vi0.972.323.109 (17)138
Symmetry codes: (i) x, y+1, z+2; (ii) x, y+1, z+1; (iii) x, y+2, z+1; (iv) x+1, y+1, z+2; (v) x+1, y+1, z+1; (vi) x, y1, z.
 

Acknowledgements

This scientific work has been supported from funds for science in years 2007–2009 as a research project (N. N204 0355 33 and DS/8210-4-0086-8).

References

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Volume 65| Part 1| January 2009| Pages m25-m26
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