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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m886–m887.
Published online 2008 June 7. doi:  10.1107/S1600536808014396
PMCID: PMC2961776

Di-μ-oxido-bis­{[(R,R)-(+)-1-amino-2-(3-methoxy-2-oxidobenzyl­ideneamino-κ2 O 2,N)-1,2-diphenyl­ethane-κN]oxidovanadium(V)} dihydrate

Abstract

In the crystal structure of the title compound, [V2(C22H21N2O2)2O4]·2H2O, oxide-bridged dimers of the complex are linked to water mol­ecules by hydrogen-bonding inter­actions. The two five-membered chelate rings in the dimeric mol­ecule both adopt twist conformations. Each VV atom is six-coordinated by one oxide group and by two N and one O atom of the tridentate Schiff base ligand, and is bridged by two additional oxide atoms. The metal centre has a distorted octa­hedral coordination. The monoanionic ligands occupy one equatorial and two axial positions.

Related literature

For general background, see: Robinson et al. (1986 [triangle]); Vilter (1984 [triangle]); Gruning & Rehder (2000 [triangle]); Casny & Rehder (2001 [triangle]); Kimblin et al. (2002 [triangle]); Kwiatkowski et al. (2003 [triangle], 2007 [triangle]); Romanowski et al. (2008 [triangle]); Wever & Hemrika (1997 [triangle]); Butler & Carter-Franklin (2004 [triangle]). For related structures, see: Root et al. (1993 [triangle]); Romanowski et al. (2008 [triangle]); Colpas et al. (1994 [triangle]); Li et al. (1988 [triangle]). For the synthesis, see: Kwiatkowski et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m886-scheme1.jpg

Experimental

Crystal data

  • [V2(C22H21N2O2)2O4]·2H2O
  • M r = 892.73
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m886-efi1.jpg
  • a = 9.328 (4) Å
  • b = 16.950 (7) Å
  • c = 25.490 (10) Å
  • V = 4030 (3) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 4.44 mm−1
  • T = 100 (2) K
  • 0.14 × 0.12 × 0.09 mm

Data collection

  • Oxford Xcalibur PX diffractometer with CCD area-detector
  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.627, T max = 0.768
  • 27320 measured reflections
  • 7083 independent reflections
  • 3677 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.069
  • S = 1.01
  • 7083 reflections
  • 541 parameters
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.39 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2905 Friedel pairs
  • Flack parameter: −0.007 (9)

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.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014396/xu2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014396/xu2414Isup2.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 (Nos. N204 0355 33 and DS/8210–4-0086–8).

supplementary crystallographic information

Comment

The discovery of vanadium in active sites of biological systems of nitrogenase (Robinson et al., 1986) and bromoperoxidase (Vilter, 1984) and recognition of its environment increased the interest in the vanadium complexes with ligands bearing oxygen and nitrogen atoms for mimicking the biological activity in natural systems. Structural models for the active site in haloperoxidases have already been reported (Gruning & Rehder, 2000; Casny & Rehder, 2001; Kimblin et al., 2002). Recently, it has been established that vanadium(V) complexes with Schiff bases, which are excellent models for active sites of vanadium containing haloperoxidases, are able to catalyze the oxidation of organic sulfides to the corresponding sulfoxides (Kwiatkowski et al., 2003, 2007; Romanowski et al., 2008). Vanadium haloperoxidases catalyze the oxidation of halides in the presence of hydrogen peroxide to highly reactive intermediate, a hypohalous acid, which may react either with suitable nucleophilic acceptor, if present, forming a halogenated compound or with hydrogen peroxide yielding 1O2 (Wever & Hemrika, 1997). Lately, it has been shown that vanadium bromoperoxidase from marine red algae can catalyze the bromination and cyclization of terpene substrates or the selective sulfoxidation of sulfides to the sulfoxides (Butler & Carter-Franklin, 2004).

The structure of (I) indicates that each vanadium atom is six-coordinated. The vanadium atoms V27 and V27A are joined together through two oxygen bridges, O29 and O29A being the bridging atoms coordinated to vanadium atoms at short and long distances (Table 1 and Fig. 1). The coordination sphere around each vanadium atom is composed of phenolate oxygen atoms (O7 or O7A) and of primary amine nitrogen atom (N14 or N14A) occupying axial positions and of imine nitrogen atom (N11 or N11A), two strongly coordinated terminal oxo (O28, O29 or O28A, O29A) and one weakly associated oxo group (O29A or O29) derived from the neighbouring VO2 unit defining the equatorial plane. The polyhedron that describes the quadrilateral core consisting of the V2O2 unit and the spatial arrangement of remaining coordinated atoms resembles two edge shared octahedrons that are significantly distorted. The V27=O28 and V27A=O28A bond lengths of 1.616 (4) and 1.612 (4) Å respectively compare well with the distances between vanadium and the doubly bonded oxygen atoms (Root et al., 1993; Romanowski et al., 2008). The V27—O29 and V27A—O29A bonds (average 1.696 (4) Å) are longer than V27—O28 and V27A—O28A bonds (average 1.614 (4) Å) due to involvement of O29 and O29A atoms in V27—V27A bridging and hydrogen bonding interactions with water molecules. The V27—V27A distance of 3.057 (2) Å is much shorter than the V(V)—V(V) distance of 3.204 Å found in similar complex (Romanowski et al., 2008). The O28—V27—O29 and O28A—V27A—O29A angles of 105.6 (2)° and 104.6 (2)° respectively indicate significant double bond character of these bonds (Colpas et al., 1994) and are close to other cis-VO2 units (Li et al., 1988). The two five-membered chelate rings adopt twisted conformations, while in similar dimeric vanadium(V) complex adopt differently puckered envelope conformations (Romanowski et al., 2008). The rings defined by V27, N11, C12, C13, N14 and V27A, N11A, C12A, C13A, N14A choose twisted conformation on C12, C13 and C12A, C13A, respectively.

The crystal structure of (I) is stabilized by intermolecular hydrogen bonds linking dimeric molecules both directly by N—H···O interactions and indirectly through water molecules by O···H—O—H interactions (Fig. 2, Table 2).

Experimental

The complex (I) were obtained in a template/complexation reactions analogous to those described for preparation of dioxovanadium(V) complexes with Schiff base ligands (Kwiatkowski et al., 2003). A solution of 1 mmol of (R,R)-(+)-1,2-diphenyl-1,2-diaminoethane in 10 ml of absolute ethanol was added under stirring to a freshly filtered solution of vanadium(V) oxytriethoxide (1 mmol) in 50 ml of absolute EtOH producing a yellow suspension of the intermediate. 3-Methoxysalicylaldehyde (1 mmol) dissolved in absolute EtOH was added to the aforementioned suspension. After refluxing (70 ml) of the resulting mixture for 2 h and its cooling to room temperature the separated solids were filtered off, washed several times with EtOH, recrystallized from DMSO-EtOH mixture and dried over molecular sieves.

Refinement

All C bonded H atoms were positioned geometrically and refined using a riding model, with C–H distances of 0.93–1.00 Å and with Uiso(H) = 1.2Ueq(C) (C–H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl group). All remaining H atoms were found in difference Fourier maps and their positions were refined initially with O–H and N–H bond lengths restricted to be 0.92 and 0.84 Å, respectively. In the final stages of refinement these H atoms were constrained to ride on their parent atoms using AFIX 23 and AFIX 3, respectively; (Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O)). One H atom from each water molecule is not involved in any hydrogen bonds; an observation confirmed by its IR spectrum which shows a single sharp band at 935 cm-1.

Figures

Fig. 1.
ORTEPII plot (Johnson, 1976) of the title complex, with displacement ellipsoids drawn at the 15% probability level and H atoms are shown as small spheres of arbitrary radius.
Fig. 2.
The structure of (I) with water molecules showing hydrogen bonding arrangement.

Crystal data

[V2(C22H21N2O2)2O4]·2H2OF000 = 1856
Mr = 892.73Dx = 1.471 Mg m3
Orthorhombic, P212121Cu Kα radiation λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 12243 reflections
a = 9.328 (4) Åθ = 3–70º
b = 16.950 (7) ŵ = 4.44 mm1
c = 25.490 (10) ÅT = 100 (2) K
V = 4030 (3) Å3Multifaced, violet
Z = 40.14 × 0.12 × 0.09 mm

Data collection

Oxford Xcalibur PX κ-geometry diffractometer with CCD area-detector7083 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 100(2) Kθmax = 76.5º
ω and [var phi] scansθmin = 3.1º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2006)h = −10→11
Tmin = 0.627, Tmax = 0.768k = −19→20
27320 measured reflectionsl = −20→31

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048  w = 1/[σ2(Fo2) + (0.009P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max = 0.004
S = 1.01Δρmax = 0.64 e Å3
7083 reflectionsΔρmin = −0.39 e Å3
541 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2905 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.007 (9)

Special details

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.

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

xyzUiso*/Ueq
V27A0.32884 (10)0.48070 (7)0.48510 (4)0.0321 (3)
V270.64395 (9)0.51515 (7)0.50926 (4)0.0315 (3)
O28A0.2087 (4)0.4322 (2)0.45349 (16)0.0364 (12)
O280.7674 (4)0.5616 (2)0.54082 (16)0.0351 (12)
O29A0.4860 (4)0.4571 (3)0.45501 (15)0.0319 (12)
O290.4883 (3)0.5398 (3)0.53930 (15)0.0292 (11)
O7A0.3123 (4)0.5855 (2)0.45846 (15)0.0300 (11)
C1A0.2145 (6)0.6399 (4)0.4629 (2)0.0276 (16)
C2A0.2227 (6)0.7066 (4)0.4286 (2)0.0267 (16)
C3A0.1167 (6)0.7649 (4)0.4295 (2)0.0291 (17)
H3A0.12020.80720.40510.035*
C4A0.0064 (6)0.7611 (4)0.4659 (3)0.0320 (18)
H4A−0.06590.80060.46640.038*
C5A0.0025 (5)0.7001 (4)0.5010 (2)0.0263 (17)
H5A−0.07160.69870.52660.032*
C6A0.1035 (5)0.6405 (3)0.5004 (2)0.0211 (14)
O8A0.3392 (4)0.7063 (3)0.39578 (15)0.0332 (12)
C9A0.3526 (7)0.7745 (4)0.3617 (2)0.0395 (19)
H9D0.43980.76950.34050.059*
H9E0.35840.82250.38310.059*
H9F0.26890.77760.33860.059*
C10A0.0956 (6)0.5785 (4)0.5396 (2)0.0296 (17)
H10A0.02190.58350.56510.036*
N11A0.1760 (5)0.5186 (3)0.54371 (16)0.0256 (12)
C12A0.1482 (5)0.4612 (3)0.58662 (19)0.0311 (14)
H12A0.08700.41830.57150.037*
C15A0.0728 (6)0.4914 (4)0.6338 (2)0.0291 (16)
C20A0.1342 (6)0.5481 (4)0.6645 (2)0.0367 (17)
H20A0.22600.56810.65540.044*
C19A0.0649 (7)0.5771 (4)0.7088 (2)0.052 (2)
H19A0.10900.61690.72950.063*
C18A−0.0669 (8)0.5481 (4)0.7227 (3)0.053 (2)
H18A−0.11160.56620.75390.063*
C17A−0.1363 (7)0.4922 (5)0.6913 (2)0.057 (2)
H17A−0.22930.47310.69960.068*
C16A−0.0610 (6)0.4657 (4)0.6467 (2)0.043 (2)
H16A−0.10580.42800.62450.051*
C13A0.2980 (6)0.4236 (3)0.5991 (2)0.0299 (16)
H13A0.36230.46640.61240.036*
N14A0.3554 (5)0.3965 (3)0.54722 (18)0.0324 (14)
H14C0.30970.35040.53800.039*
H14D0.45140.38540.55080.039*
C21A0.2923 (6)0.3601 (4)0.6398 (2)0.0282 (17)
C26A0.3591 (7)0.3697 (4)0.6877 (2)0.0386 (16)
H26A0.41200.41670.69370.046*
C25A0.3528 (8)0.3160 (4)0.7261 (2)0.050 (2)
H25A0.40120.32430.75850.060*
C24A0.2750 (7)0.2486 (4)0.7177 (3)0.051 (2)
H24A0.26920.21050.74490.061*
C23A0.2058 (6)0.2345 (4)0.6716 (2)0.0465 (18)
H23A0.15500.18670.66590.056*
C22A0.2121 (6)0.2926 (4)0.6331 (2)0.0440 (19)
H22A0.15990.28560.60150.053*
O70.6590 (4)0.4115 (2)0.53751 (16)0.0315 (11)
C10.7654 (6)0.3571 (4)0.5352 (2)0.0274 (16)
C20.7597 (6)0.2964 (4)0.5720 (2)0.0259 (16)
C30.8644 (6)0.2387 (4)0.5706 (2)0.0292 (16)
H30.86260.19710.59550.035*
C40.9722 (6)0.2413 (4)0.5331 (3)0.038 (2)
H41.04440.20170.53280.046*
C50.9748 (6)0.3004 (4)0.4967 (2)0.0367 (18)
H51.04850.30140.47090.044*
C60.8726 (6)0.3580 (3)0.4969 (2)0.0224 (14)
O80.6476 (4)0.2980 (3)0.60580 (15)0.0332 (12)
C90.6331 (6)0.2312 (4)0.6400 (2)0.043 (2)
H9A0.54820.23800.66230.065*
H9B0.71860.22670.66220.065*
H9C0.62250.18310.61900.065*
C100.8681 (6)0.4112 (4)0.4535 (2)0.0279 (16)
H100.93460.40190.42600.033*
N110.7841 (4)0.4701 (3)0.44777 (18)0.0287 (13)
C120.7728 (5)0.5126 (3)0.39691 (19)0.0315 (14)
H120.68910.48970.37770.038*
C150.9029 (5)0.5043 (4)0.3612 (2)0.0243 (16)
C200.8946 (7)0.4590 (4)0.3158 (2)0.044 (2)
H200.80830.43180.30780.053*
C191.0104 (7)0.4531 (4)0.2821 (3)0.049 (2)
H191.00400.42210.25110.059*
C181.1345 (7)0.4925 (4)0.2941 (2)0.0430 (18)
H181.21350.48950.27070.052*
C171.1468 (6)0.5357 (4)0.3387 (2)0.0507 (19)
H171.23370.56220.34710.061*
C161.0299 (6)0.5401 (4)0.3714 (2)0.046 (2)
H161.03860.56990.40280.055*
C130.7381 (5)0.5996 (3)0.4075 (2)0.0260 (15)
H130.82670.62490.42180.031*
N140.6256 (5)0.6028 (3)0.44947 (18)0.0320 (14)
H14A0.53710.59780.43390.038*
H14B0.62900.65170.46510.038*
C210.7018 (6)0.6405 (4)0.3576 (2)0.0288 (17)
C260.5853 (6)0.6156 (4)0.3278 (2)0.0420 (19)
H260.52770.57360.34050.050*
C250.5504 (7)0.6501 (4)0.2800 (2)0.0512 (19)
H250.46930.63370.26020.061*
C240.6411 (8)0.7102 (5)0.2627 (2)0.056 (2)
H240.62250.73300.22930.067*
C230.7545 (7)0.7383 (5)0.2906 (3)0.068 (3)
H230.81160.78050.27780.082*
C220.7839 (6)0.7026 (4)0.3390 (2)0.050 (2)
H220.86170.72140.35950.060*
O1W0.4465 (5)0.4178 (3)0.3495 (2)0.0770 (18)
H1W10.41210.43970.37620.115*
H2W10.48210.37340.35640.115*
O2W0.5401 (7)0.5739 (4)0.6465 (2)0.132 (3)
H1W20.52920.57690.61380.199*
H2W20.62600.56720.65530.199*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
V27A0.0266 (6)0.0352 (7)0.0346 (6)0.0044 (5)0.0053 (5)0.0018 (7)
V270.0244 (5)0.0340 (7)0.0361 (6)0.0034 (5)0.0068 (5)0.0017 (6)
O28A0.030 (2)0.039 (3)0.040 (3)−0.003 (2)−0.002 (2)−0.001 (2)
O280.027 (2)0.042 (3)0.036 (3)−0.008 (2)0.002 (2)−0.010 (2)
O29A0.029 (2)0.029 (3)0.038 (3)0.003 (2)0.011 (2)−0.003 (2)
O290.024 (2)0.028 (3)0.036 (3)0.004 (2)0.0124 (19)−0.001 (2)
O7A0.022 (2)0.034 (3)0.035 (3)0.002 (2)0.012 (2)0.005 (2)
C1A0.028 (4)0.025 (4)0.030 (4)0.000 (3)−0.002 (3)−0.006 (3)
C2A0.020 (3)0.028 (4)0.032 (4)−0.005 (3)−0.001 (3)−0.001 (4)
C3A0.025 (3)0.029 (4)0.033 (4)−0.001 (3)−0.006 (3)0.004 (3)
C4A0.025 (3)0.039 (5)0.031 (4)0.004 (3)0.001 (3)−0.008 (4)
C5A0.016 (3)0.035 (5)0.028 (4)0.005 (3)0.007 (3)−0.002 (4)
C6A0.017 (3)0.024 (4)0.022 (3)−0.006 (3)0.005 (3)−0.004 (3)
O8A0.024 (2)0.036 (3)0.040 (3)0.001 (2)0.013 (2)0.001 (2)
C9A0.053 (4)0.036 (5)0.030 (4)−0.002 (4)0.005 (4)0.017 (3)
C10A0.026 (3)0.040 (5)0.024 (3)−0.013 (3)0.004 (3)−0.014 (3)
N11A0.028 (3)0.020 (3)0.028 (3)0.005 (3)−0.001 (2)−0.004 (3)
C12A0.034 (3)0.034 (4)0.026 (3)0.003 (3)0.006 (3)0.009 (3)
C15A0.031 (3)0.031 (5)0.025 (3)0.001 (3)0.002 (3)−0.001 (3)
C20A0.030 (4)0.044 (4)0.036 (4)0.007 (3)0.002 (3)−0.007 (3)
C19A0.068 (5)0.052 (5)0.036 (4)0.026 (4)−0.001 (4)−0.004 (4)
C18A0.061 (5)0.058 (6)0.039 (5)0.025 (4)0.026 (4)0.003 (4)
C17A0.054 (4)0.072 (6)0.044 (4)0.011 (5)0.017 (4)−0.002 (5)
C16A0.035 (4)0.050 (5)0.044 (5)−0.001 (4)0.004 (3)0.011 (4)
C13A0.024 (3)0.035 (4)0.030 (4)0.009 (3)0.001 (3)0.006 (3)
N14A0.025 (3)0.038 (4)0.034 (3)0.006 (3)0.003 (3)−0.006 (3)
C21A0.023 (3)0.030 (4)0.032 (4)0.013 (3)0.000 (3)−0.002 (3)
C26A0.051 (4)0.024 (4)0.040 (4)0.004 (4)0.000 (4)−0.001 (3)
C25A0.073 (6)0.046 (5)0.031 (4)0.001 (5)0.007 (4)−0.005 (4)
C24A0.057 (5)0.060 (6)0.037 (5)0.013 (5)0.027 (4)0.014 (4)
C23A0.045 (4)0.047 (5)0.048 (4)−0.004 (4)0.004 (3)0.012 (4)
C22A0.038 (4)0.049 (5)0.045 (4)−0.002 (3)−0.004 (3)0.005 (4)
O70.016 (2)0.035 (3)0.044 (3)0.008 (2)0.005 (2)−0.006 (2)
C10.018 (3)0.031 (4)0.033 (4)−0.002 (3)−0.006 (3)−0.008 (4)
C20.026 (4)0.020 (4)0.032 (4)−0.001 (3)−0.004 (3)0.000 (4)
C30.032 (4)0.028 (4)0.027 (4)−0.005 (4)−0.002 (3)0.001 (3)
C40.022 (3)0.043 (5)0.050 (5)0.013 (4)0.007 (3)−0.006 (4)
C50.036 (4)0.041 (5)0.033 (5)0.004 (4)0.008 (4)0.003 (4)
C60.019 (3)0.020 (3)0.028 (4)0.008 (3)0.000 (3)0.005 (3)
O80.025 (2)0.040 (3)0.035 (3)−0.001 (2)0.015 (2)0.003 (2)
C90.041 (4)0.056 (6)0.033 (4)0.003 (4)0.005 (3)0.011 (4)
C100.022 (3)0.029 (4)0.033 (4)0.003 (3)0.009 (3)−0.010 (3)
N110.024 (3)0.031 (3)0.031 (3)0.002 (3)−0.005 (2)−0.005 (3)
C120.023 (3)0.046 (4)0.025 (3)−0.006 (3)0.002 (2)−0.005 (3)
C150.019 (3)0.030 (4)0.024 (3)0.002 (3)0.003 (2)−0.003 (3)
C200.036 (4)0.058 (5)0.038 (4)0.001 (4)0.000 (3)0.000 (4)
C190.048 (4)0.068 (6)0.031 (4)0.016 (4)0.007 (4)−0.013 (4)
C180.039 (4)0.053 (5)0.037 (4)0.009 (4)0.014 (3)0.009 (4)
C170.045 (4)0.064 (5)0.043 (4)−0.009 (4)0.019 (4)−0.010 (4)
C160.019 (3)0.075 (6)0.044 (4)0.002 (4)0.006 (3)−0.019 (4)
C130.021 (3)0.029 (4)0.028 (3)0.001 (3)0.006 (3)−0.001 (3)
N140.029 (3)0.025 (4)0.043 (3)0.007 (3)0.004 (3)−0.004 (3)
C210.017 (3)0.046 (5)0.023 (4)0.002 (3)0.002 (3)0.007 (3)
C260.032 (4)0.062 (5)0.032 (4)0.015 (4)0.005 (3)0.004 (4)
C250.049 (5)0.067 (5)0.037 (4)0.018 (4)−0.011 (4)0.000 (4)
C240.058 (5)0.087 (7)0.023 (4)0.023 (5)0.016 (4)0.019 (4)
C230.038 (5)0.107 (8)0.060 (6)0.003 (5)0.010 (4)0.037 (5)
C220.031 (4)0.078 (6)0.040 (4)−0.001 (4)−0.006 (3)0.022 (4)
O1W0.094 (4)0.058 (4)0.078 (5)0.009 (3)0.023 (3)−0.003 (3)
O2W0.171 (6)0.149 (7)0.076 (5)−0.062 (5)0.006 (4)−0.002 (5)

Geometric parameters (Å, °)

V27A—O7A1.908 (4)C24A—H24A0.9500
V27A—O28A1.607 (4)C23A—C22A1.391 (7)
V27A—O29A1.703 (4)C23A—H23A0.9500
V27A—O292.263 (4)C22A—H22A0.9500
V27A—N11A2.163 (5)O7—C11.356 (7)
V27A—N14A2.147 (5)C1—C21.393 (8)
V27A—V273.0595 (17)C1—C61.398 (7)
V27—O71.904 (4)C2—O81.356 (6)
V27—O281.610 (4)C2—C31.382 (8)
V27—O291.694 (3)C3—C41.388 (8)
V27—O29A2.247 (4)C3—H30.9500
V27—N112.179 (5)C4—C51.367 (8)
V27—N142.135 (5)C4—H40.9500
O7A—C1A1.302 (7)C5—C61.365 (8)
C1A—C6A1.409 (8)C5—H50.9500
C1A—C2A1.431 (8)C6—C101.428 (7)
C2A—O8A1.371 (6)O8—C91.437 (6)
C2A—C3A1.399 (8)C9—H9A0.9800
C3A—C4A1.386 (8)C9—H9B0.9800
C3A—H3A0.9500C9—H9C0.9800
C4A—C5A1.369 (8)C10—N111.276 (7)
C4A—H4A0.9500C10—H100.9500
C5A—C6A1.382 (7)N11—C121.487 (6)
C5A—H5A0.9500C12—C151.523 (6)
C6A—C10A1.453 (8)C12—C131.535 (7)
O8A—C9A1.451 (6)C12—H121.0000
C9A—H9D0.9800C15—C161.357 (7)
C9A—H9E0.9800C15—C201.391 (7)
C9A—H9F0.9800C20—C191.383 (8)
C10A—N11A1.267 (7)C20—H200.9500
C10A—H10A0.9500C19—C181.371 (8)
N11A—C12A1.487 (6)C19—H190.9500
C12A—C15A1.485 (7)C18—C171.359 (7)
C12A—C13A1.568 (7)C18—H180.9500
C12A—H12A1.0000C17—C161.374 (7)
C15A—C16A1.363 (7)C17—H170.9500
C15A—C20A1.365 (8)C16—H160.9500
C20A—C19A1.391 (7)C13—C211.487 (7)
C20A—H20A0.9500C13—N141.500 (6)
C19A—C18A1.370 (8)C13—H131.0000
C19A—H19A0.9500N14—H14A0.9200
C18A—C17A1.399 (9)N14—H14B0.9200
C18A—H18A0.9500C21—C221.386 (8)
C17A—C16A1.411 (8)C21—C261.391 (7)
C17A—H17A0.9500C26—C251.389 (8)
C16A—H16A0.9500C26—H260.9500
C13A—C21A1.497 (8)C25—C241.396 (9)
C13A—N14A1.499 (6)C25—H250.9500
C13A—H13A1.0000C24—C231.361 (9)
N14A—H14C0.9200C24—H240.9500
N14A—H14D0.9200C23—C221.401 (9)
C21A—C22A1.377 (8)C23—H230.9500
C21A—C26A1.381 (8)C22—H220.9500
C26A—C25A1.339 (7)O1W—H1W10.8401
C26A—H26A0.9500O1W—H2W10.8402
C25A—C24A1.369 (9)O2W—H1W20.8405
C25A—H25A0.9500O2W—H2W20.8402
C24A—C23A1.362 (9)
O28A—V27A—O29A104.7 (2)C13A—N14A—H14D108.8
O28A—V27A—O7A103.99 (19)V27A—N14A—H14D108.8
O29A—V27A—O7A97.37 (19)H14C—N14A—H14D107.7
O28A—V27A—N14A96.3 (2)C22A—C21A—C26A116.9 (6)
O29A—V27A—N14A94.39 (19)C22A—C21A—C13A122.1 (6)
O7A—V27A—N14A153.03 (17)C26A—C21A—C13A120.8 (6)
O28A—V27A—N11A92.24 (19)C25A—C26A—C21A123.2 (7)
O29A—V27A—N11A161.58 (18)C25A—C26A—H26A118.4
O7A—V27A—N11A85.16 (17)C21A—C26A—H26A118.4
N14A—V27A—N11A76.36 (18)C26A—C25A—C24A118.4 (7)
O28A—V27A—O29172.23 (19)C26A—C25A—H25A120.8
O29A—V27A—O2979.23 (15)C24A—C25A—H25A120.8
O7A—V27A—O2981.88 (16)C23A—C24A—C25A122.2 (7)
N14A—V27A—O2976.60 (17)C23A—C24A—H24A118.9
N11A—V27A—O2983.10 (14)C25A—C24A—H24A118.9
O28A—V27A—V27150.30 (15)C24A—C23A—C22A117.6 (7)
O29A—V27A—V2746.21 (14)C24A—C23A—H23A121.2
O7A—V27A—V2788.38 (12)C22A—C23A—H23A121.2
N14A—V27A—V2782.40 (13)C21A—C22A—C23A121.6 (6)
N11A—V27A—V27115.95 (12)C21A—C22A—H22A119.2
O29—V27A—V2733.01 (9)C23A—C22A—H22A119.2
O28—V27—O29105.49 (19)C1—O7—V27131.7 (4)
O28—V27—O7102.1 (2)O7—C1—C2116.4 (6)
O29—V27—O796.86 (19)O7—C1—C6123.1 (6)
O28—V27—N1494.2 (2)C2—C1—C6120.4 (6)
O29—V27—N1494.74 (19)O8—C2—C3125.2 (6)
O7—V27—N14156.62 (18)O8—C2—C1116.3 (5)
O28—V27—N1195.84 (19)C3—C2—C1118.5 (6)
O29—V27—N11157.77 (18)C2—C3—C4120.5 (6)
O7—V27—N1184.50 (18)C2—C3—H3119.7
N14—V27—N1177.22 (19)C4—C3—H3119.7
O28—V27—O29A171.98 (18)C5—C4—C3120.2 (6)
O29—V27—O29A79.87 (15)C5—C4—H4119.9
O7—V27—O29A82.93 (17)C3—C4—H4119.9
N14—V27—O29A79.22 (17)C6—C5—C4120.6 (6)
N11—V27—O29A78.29 (14)C6—C5—H5119.7
O28—V27—V27A151.77 (14)C4—C5—H5119.7
O29—V27—V27A46.71 (14)C5—C6—C1119.7 (6)
O7—V27—V27A88.33 (12)C5—C6—C10118.0 (6)
N14—V27—V27A84.95 (13)C1—C6—C10121.8 (5)
N11—V27—V27A111.38 (12)C2—O8—C9116.3 (5)
O29A—V27—V27A33.16 (9)O8—C9—H9A109.5
V27A—O29A—V27100.63 (19)O8—C9—H9B109.5
V27—O29—V27A100.27 (19)H9A—C9—H9B109.5
C1A—O7A—V27A133.3 (4)O8—C9—H9C109.5
O7A—C1A—C6A125.3 (6)H9A—C9—H9C109.5
O7A—C1A—C2A117.9 (6)H9B—C9—H9C109.5
C6A—C1A—C2A116.7 (6)N11—C10—C6126.9 (5)
O8A—C2A—C3A125.0 (6)N11—C10—H10116.5
O8A—C2A—C1A114.4 (5)C6—C10—H10116.5
C3A—C2A—C1A120.7 (6)C10—N11—C12121.4 (5)
C4A—C3A—C2A120.2 (6)C10—N11—V27124.0 (4)
C4A—C3A—H3A119.9C12—N11—V27114.5 (3)
C2A—C3A—H3A119.9N11—C12—C15114.8 (5)
C5A—C4A—C3A119.5 (6)N11—C12—C13109.1 (4)
C5A—C4A—H4A120.2C15—C12—C13111.2 (5)
C3A—C4A—H4A120.2N11—C12—H12107.1
C4A—C5A—C6A121.7 (6)C15—C12—H12107.1
C4A—C5A—H5A119.1C13—C12—H12107.1
C6A—C5A—H5A119.1C16—C15—C20117.0 (5)
C5A—C6A—C1A121.0 (6)C16—C15—C12122.7 (5)
C5A—C6A—C10A119.0 (5)C20—C15—C12120.3 (5)
C1A—C6A—C10A120.0 (5)C19—C20—C15120.9 (6)
C2A—O8A—C9A115.5 (5)C19—C20—H20119.5
O8A—C9A—H9D109.5C15—C20—H20119.5
O8A—C9A—H9E109.5C18—C19—C20119.0 (6)
H9D—C9A—H9E109.5C18—C19—H19120.5
O8A—C9A—H9F109.5C20—C19—H19120.5
H9D—C9A—H9F109.5C17—C18—C19121.4 (6)
H9E—C9A—H9F109.5C17—C18—H18119.3
N11A—C10A—C6A127.3 (6)C19—C18—H18119.3
N11A—C10A—H10A116.3C18—C17—C16118.0 (6)
C6A—C10A—H10A116.3C18—C17—H17121.0
C10A—N11A—C12A118.8 (5)C16—C17—H17121.0
C10A—N11A—V27A124.9 (4)C15—C16—C17123.6 (6)
C12A—N11A—V27A115.3 (3)C15—C16—H16118.2
C15A—C12A—N11A116.9 (5)C17—C16—H16118.2
C15A—C12A—C13A113.4 (4)C21—C13—N14115.7 (5)
N11A—C12A—C13A105.0 (4)C21—C13—C12110.2 (5)
C15A—C12A—H12A107.0N14—C13—C12107.9 (4)
N11A—C12A—H12A107.0C21—C13—H13107.6
C13A—C12A—H12A107.0N14—C13—H13107.6
C16A—C15A—C20A118.1 (6)C12—C13—H13107.6
C16A—C15A—C12A121.2 (6)C13—N14—V27115.4 (3)
C20A—C15A—C12A120.6 (5)C13—N14—H14A108.4
C15A—C20A—C19A121.3 (6)V27—N14—H14A108.4
C15A—C20A—H20A119.4C13—N14—H14B108.4
C19A—C20A—H20A119.4V27—N14—H14B108.4
C18A—C19A—C20A120.0 (7)H14A—N14—H14B107.5
C18A—C19A—H19A120.0C22—C21—C26118.3 (6)
C20A—C19A—H19A120.0C22—C21—C13121.4 (6)
C19A—C18A—C17A120.7 (7)C26—C21—C13120.3 (6)
C19A—C18A—H18A119.6C25—C26—C21122.4 (6)
C17A—C18A—H18A119.6C25—C26—H26118.8
C18A—C17A—C16A116.5 (7)C21—C26—H26118.8
C18A—C17A—H17A121.7C26—C25—C24116.2 (6)
C16A—C17A—H17A121.7C26—C25—H25121.9
C15A—C16A—C17A123.3 (7)C24—C25—H25121.9
C15A—C16A—H16A118.4C23—C24—C25124.2 (7)
C17A—C16A—H16A118.4C23—C24—H24117.9
C21A—C13A—N14A113.8 (5)C25—C24—H24117.9
C21A—C13A—C12A113.6 (4)C24—C23—C22117.5 (7)
N14A—C13A—C12A105.3 (4)C24—C23—H23121.3
C21A—C13A—H13A108.0C22—C23—H23121.3
N14A—C13A—H13A108.0C21—C22—C23121.4 (6)
C12A—C13A—H13A108.0C21—C22—H22119.3
C13A—N14A—V27A113.9 (3)C23—C22—H22119.3
C13A—N14A—H14C108.8H1W1—O1W—H2W1112.2
V27A—N14A—H14C108.8H1W2—O2W—H2W2112.9
O7A—C1A—C2A—O8A−2.6 (8)C13A—C21A—C22A—C23A−179.0 (5)
C6A—C1A—C2A—O8A174.9 (5)C24A—C23A—C22A—C21A3.8 (9)
O7A—C1A—C2A—C3A176.6 (5)O7—C1—C2—O80.5 (8)
C6A—C1A—C2A—C3A−5.9 (9)C6—C1—C2—O8−176.5 (5)
O8A—C2A—C3A—C4A−177.2 (6)O7—C1—C2—C3178.9 (5)
C1A—C2A—C3A—C4A3.7 (9)C6—C1—C2—C31.9 (9)
C2A—C3A—C4A—C5A0.3 (10)O8—C2—C3—C4177.8 (6)
C3A—C4A—C5A—C6A−2.0 (10)C1—C2—C3—C4−0.4 (9)
C4A—C5A—C6A—C1A−0.5 (9)C2—C3—C4—C5−0.8 (10)
C4A—C5A—C6A—C10A178.3 (6)C3—C4—C5—C60.5 (11)
O7A—C1A—C6A—C5A−178.4 (6)C4—C5—C6—C10.9 (10)
C2A—C1A—C6A—C5A4.4 (8)C4—C5—C6—C10−170.8 (6)
O7A—C1A—C6A—C10A2.8 (9)O7—C1—C6—C5−179.0 (6)
C2A—C1A—C6A—C10A−174.5 (5)C2—C1—C6—C5−2.2 (9)
C3A—C2A—O8A—C9A2.8 (8)O7—C1—C6—C10−7.5 (9)
C1A—C2A—O8A—C9A−178.1 (5)C2—C1—C6—C10169.3 (6)
C5A—C6A—C10A—N11A177.6 (5)C3—C2—O8—C9−4.6 (8)
C1A—C6A—C10A—N11A−3.5 (9)C1—C2—O8—C9173.6 (5)
C6A—C10A—N11A—C12A−179.0 (5)C5—C6—C10—N11−177.3 (6)
C6A—C10A—N11A—V27A−10.7 (8)C1—C6—C10—N1111.1 (10)
C10A—N11A—C12A—C15A−24.9 (7)C6—C10—N11—C12−169.2 (5)
C10A—N11A—C12A—C13A−151.6 (5)C6—C10—N11—V279.4 (8)
N11A—C12A—C15A—C16A114.2 (7)C10—N11—C12—C15−23.2 (7)
C13A—C12A—C15A—C16A−123.4 (6)C10—N11—C12—C13−148.8 (5)
N11A—C12A—C15A—C20A−63.5 (7)N11—C12—C15—C16−71.8 (8)
C13A—C12A—C15A—C20A59.0 (8)C13—C12—C15—C1652.7 (8)
C16A—C15A—C20A—C19A2.2 (9)N11—C12—C15—C20108.6 (6)
C12A—C15A—C20A—C19A180.0 (6)C13—C12—C15—C20−126.8 (6)
C15A—C20A—C19A—C18A0.7 (10)C16—C15—C20—C19−1.7 (10)
C20A—C19A—C18A—C17A−3.1 (11)C12—C15—C20—C19177.9 (6)
C19A—C18A—C17A—C16A2.6 (11)C15—C20—C19—C180.1 (10)
C20A—C15A—C16A—C17A−2.8 (10)C20—C19—C18—C171.4 (11)
C12A—C15A—C16A—C17A179.5 (6)C19—C18—C17—C16−1.1 (11)
C18A—C17A—C16A—C15A0.4 (11)C20—C15—C16—C172.0 (11)
C15A—C12A—C13A—C21A54.4 (7)C12—C15—C16—C17−177.6 (6)
N11A—C12A—C13A—C21A−176.8 (5)C18—C17—C16—C15−0.6 (11)
C15A—C12A—C13A—N14A179.5 (5)N11—C12—C13—C21−170.4 (4)
N11A—C12A—C13A—N14A−51.7 (6)C15—C12—C13—C2161.9 (6)
C21A—C13A—N14A—V27A169.5 (4)N11—C12—C13—N14−43.1 (5)
C12A—C13A—N14A—V27A44.5 (5)C15—C12—C13—N14−170.8 (4)
O28A—V27A—N14A—C13A−109.7 (4)C21—C13—N14—V27160.3 (4)
O29A—V27A—N14A—C13A144.9 (4)C12—C13—N14—V2736.4 (5)
O7A—V27A—N14A—C13A29.1 (6)N14—C13—C21—C22119.4 (6)
N11A—V27A—N14A—C13A−18.9 (4)C12—C13—C21—C22−117.9 (6)
O29—V27A—N14A—C13A67.1 (4)N14—C13—C21—C26−62.0 (8)
N14A—C13A—C21A—C22A−60.2 (7)C12—C13—C21—C2660.7 (7)
C12A—C13A—C21A—C22A60.3 (8)C22—C21—C26—C250.9 (9)
N14A—C13A—C21A—C26A124.8 (6)C13—C21—C26—C25−177.7 (6)
C12A—C13A—C21A—C26A−114.7 (6)C21—C26—C25—C241.6 (9)
C22A—C21A—C26A—C25A2.3 (10)C26—C25—C24—C23−3.2 (10)
C13A—C21A—C26A—C25A177.5 (6)C25—C24—C23—C222.1 (12)
C21A—C26A—C25A—C24A−0.8 (11)C26—C21—C22—C23−2.1 (10)
C26A—C25A—C24A—C23A0.7 (11)C13—C21—C22—C23176.5 (6)
C25A—C24A—C23A—C22A−2.2 (10)C24—C23—C22—C210.7 (11)
C26A—C21A—C22A—C23A−3.8 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N14—H14A···O7A0.922.202.946 (6)138
N14A—H14D···O70.922.022.855 (6)151
O1W—H1W1···O29A0.842.142.795 (6)134
O2W—H1W2···O290.842.042.834 (7)158
C3—H3···O1Wi0.952.523.431 (8)160
C3A—H3A···O2Wii0.952.523.424 (9)159
C10A—H10A···O28iii0.952.483.075 (7)120
C13A—H13A···O291.002.533.057 (7)113

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2414).

References

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