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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m25–m26.
Published online 2008 December 10. doi:  10.1107/S1600536808038762
PMCID: PMC2967873

Di-μ-oxido-bis­({2-[(R,R)-(−)-(2-amino­cyclo­hexyl)imino­meth­yl]-4-nitro­phenolato-κ3 N,N′,O}oxidovanadium(V)) dimethyl sulfoxide disolvate

Abstract

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

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Object name is e-65-00m25-scheme1.jpg

Experimental

Crystal data

  • [V2(C13H16N3O3)2O4]·2C2H6OS
  • M r = 846.71
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m25-efi1.jpg
  • 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 [triangle]) T min = 0.720, T max = 0.936
  • 6786 measured reflections
  • 3355 independent reflections
  • 3245 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 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

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

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038762/hy2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038762/hy2164Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.]
Fig. 2.
The arrangement of molecules in the title compound, viewed approximately along the a axis. Hydrogen bonds are represented by dashed lines.

Crystal data

[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

Oxford Diffraction Ruby CCD diffractometer3355 independent reflections
Radiation source: Enhance (Mo) X-ray Source3245 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 10.4002 pixels mm-1θmax = 25.1°, θmin = 3.0°
ω scansh = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −13→11
Tmin = 0.720, Tmax = 0.936l = −13→14
6786 measured reflections

Refinement

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) = 0.194w = 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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
H6A−0.00950.91510.81970.048*
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)
O20−0.0303 (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)
S23−0.0005 (3)0.6916 (2)0.44455 (18)0.0657 (6)
C240.0490 (17)0.8021 (9)0.5086 (8)0.094 (3)
H24A−0.02720.87910.47110.140*
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*
O26−0.0092 (10)0.7404 (5)0.3172 (5)0.0747 (17)

Atomic displacement parameters (Å2)

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, °)

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—C3−176.9 (5)C15—C16—C17—N18−179.6 (8)
C6—C1—C2—C30.2 (8)C17A—C16—C17—N18−64.4 (11)
O22—C1—C2—C104.5 (8)C15A—C16—C17—N18−137.2 (10)
C6—C1—C2—C10−178.4 (5)C15—C16—C17—C12−64.7 (12)
C1—C2—C3—C4−1.6 (9)C17A—C16—C17—C1250.5 (11)
C10—C2—C3—C4177.1 (6)C15A—C16—C17—C12−22.3 (14)
C2—C3—C4—C5−0.1 (11)N11—C12A—C17A—N1855.5 (12)
C2—C3—C4—N7−179.9 (7)C13—C12A—C17A—N18178.1 (9)
C3—C4—C5—C63.0 (12)N11—C12A—C17A—C16170.9 (9)
N7—C4—C5—C6−177.2 (7)C13—C12A—C17A—C16−66.5 (13)
C4—C5—C6—C1−4.4 (11)C15—C16—C17A—N18141.3 (9)
O22—C1—C6—C5−180.0 (6)C17—C16—C17A—N1864.3 (12)
C2—C1—C6—C52.8 (9)C15A—C16—C17A—N18−176.0 (9)
C3—C4—N7—O9−13.0 (13)C15—C16—C17A—C12A28.3 (14)
C5—C4—N7—O9167.2 (9)C17—C16—C17A—C12A−48.7 (12)
C3—C4—N7—O8166.1 (8)C15A—C16—C17A—C12A71.0 (12)
C5—C4—N7—O8−13.7 (13)C12—C17—N18—C17A−51.4 (11)
C3—C2—C10—N11−165.8 (6)C16—C17—N18—C17A64.7 (11)
C1—C2—C10—N1112.8 (9)C12—C17—N18—V1945.1 (10)
C2—C10—N11—C12−167.3 (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—C17−64.9 (12)
C10—N11—C12—C13−20.5 (15)C12A—C17A—N18—V19−51.1 (11)
C12A—N11—C12—C1373 (2)C16—C17A—N18—V19−163.6 (6)
V19—N11—C12—C13169.7 (8)C17—N18—V19—O2082.6 (6)
C10—N11—C12—C17−144.0 (8)C17A—N18—V19—O20120.2 (7)
C12A—N11—C12—C17−50.9 (19)C17—N18—V19—O21i−170.4 (6)
V19—N11—C12—C1746.2 (11)C17A—N18—V19—O21i−132.7 (7)
C10—N11—C12A—C17A157.6 (8)C17—N18—V19—O22−47.4 (8)
C12—N11—C12A—C17A56 (2)C17A—N18—V19—O22−9.8 (9)
V19—N11—C12A—C17A−38.3 (12)C17—N18—V19—N11−15.1 (6)
C10—N11—C12A—C1336.8 (14)C17A—N18—V19—N1122.6 (6)
C12—N11—C12A—C13−65 (2)C17—N18—V19—O21−93.4 (6)
V19—N11—C12A—C13−159.0 (8)C17A—N18—V19—O21−55.8 (7)
N11—C12—C13—C14−162.4 (9)C10—N11—V19—O2080.1 (5)
C17—C12—C13—C14−43.9 (13)C12—N11—V19—O20−110.8 (7)
N11—C12—C13—C12A−73 (2)C12A—N11—V19—O20−82.7 (8)
C17—C12—C13—C12A45.4 (18)C10—N11—V19—O21i−118.1 (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—C12−52 (2)C10—N11—V19—O22−20.1 (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—C15A−13.6 (14)C12—N11—V19—N18−18.6 (7)
C12A—C13—C14—C15A−41.2 (14)C12A—N11—V19—N189.5 (7)
C15A—C14—C15—C1657.2 (12)C10—N11—V19—O21−105.7 (5)
C13—C14—C15—C16−48.9 (15)C12—N11—V19—O2163.5 (7)
C15—C14—C15A—C16−53.4 (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—V19i−95.9 (2)
C14—C15—C16—C15A−55.7 (12)N11—V19—O21—V19i−174.4 (2)
C14—C15A—C16—C1552.1 (11)C6—C1—O22—V19144.0 (4)
C14—C15A—C16—C17A−60.9 (13)C2—C1—O22—V19−38.9 (7)
C14—C15A—C16—C17−28.2 (15)O20—V19—O22—C1−58.2 (5)
N11—C12—C17—N18−57.2 (11)O21i—V19—O22—C1−167.4 (5)
C13—C12—C17—N18175.7 (9)N18—V19—O22—C170.7 (7)
N11—C12—C17—C16−174.2 (8)N11—V19—O22—C139.1 (5)
C13—C12—C17—C1658.7 (13)O21—V19—O22—C1116.0 (5)

Symmetry codes: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

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, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2164).

References

  • Carter-Franklin, J. N., Parrish, J. D., Tchirret-Guth, R. A., Little, R. D. & Butler, A. (2003). J. Am. Chem. Soc.125, 3688–3689. [PubMed]
  • Eady, R. R. (2003). Coord. Chem. Rev.237, 23–30.
  • Evangelou, A. M. (2002). Crit. Rev. Oncol. Hematol.42, 249–265. [PubMed]
  • Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Kwiatkowski, E., Romanowski, G., Nowicki, W., Kwiatkowski, M. & Suwińska, K. (2003). Polyhedron, 22, 1009–1018.
  • Kwiatkowski, E., Romanowski, G., Nowicki, W., Kwiatkowski, M. & Suwińska, K. (2007). Polyhedron, 26, 2559–2568.
  • Mendz, G. L. (1991). Arch. Biochem. Biophys.291, 201–211. [PubMed]
  • Mokry, L. M. & Carrano, C. J. (1993). Inorg. Chem.32, 6119–6121.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Parekh, H. M., Panchal, P. K. & Patel, M. N. (2006). Pharm. Chem. J. Chem.40, 494–497.
  • Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421–425.
  • Rehder, D., Antoni, G., Licini, G. M., Schulzke, C. & Meier, B. (2003). Coord. Chem. Rev.237, 53–63.
  • 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. [PubMed]
  • Romanowski, G., Kwiatkowski, E., Nowicki, W., Kwiatkowski, M. & Lis, T. (2008). Polyhedron, 27, 1601–1609.
  • Root, C. A., Hoeschele, J. D., Cornman, C. R., Kampf, J. W. & Pecoraro, V. L. (1993). Inorg. Chem.32, 3855–3861.
  • Shahzadi, S., Ali, S., Parvez, M., Badshah, A., Ahmed, E. & Malik, A. (2007). Russ. J. Inorg. Chem.52, 386–393.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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