PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m775–m776.
Published online 2008 May 7. doi:  10.1107/S1600536808010611
PMCID: PMC2961374

{2,2′-[Ethyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4 O,N,N′,O′}oxido­vanadium(IV)

Abstract

The title compound, [V(C16H14N2O2)O], was synthesized by the reaction of vanadyl(IV) sulfate and N,N′-bis­(salicyl­idene)ethyl­enediamine under hydro­thermal conditions. The asymmetric unit contains two mol­ecules. Each VIV atom is coordinated in a square-pyramidal geometry by two N atoms and two O atoms from a ligand in the basal plane and by an oxide O atom in the apical position. Weak C—H(...)O hydrogen bonds lead to a three-dimensional supra­molecular structure.

Related literature

For related literature, see: Butler & Walker (1993 [triangle]); Deng et al. (2007 [triangle]); Martinez et al. (2001 [triangle]); Sun et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m775-scheme1.jpg

Experimental

Crystal data

  • [V(C16H14N2O2)O]
  • M r = 333.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m775-efi1.jpg
  • a = 13.648 (3) Å
  • b = 6.8085 (14) Å
  • c = 15.952 (3) Å
  • β = 98.24 (3)°
  • V = 1466.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.69 mm−1
  • T = 293 (2) K
  • 0.32 × 0.21 × 0.11 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.809, T max = 0.930
  • 14358 measured reflections
  • 6102 independent reflections
  • 4561 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.109
  • S = 1.03
  • 6102 reflections
  • 397 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.43 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2456 Friedel pairs
  • Flack parameter: 0.01 (2)

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010611/hy2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010611/hy2124Isup2.hkl

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

Acknowledgments

This study was supported in part by the Natural Science Foundation of Heilongjiang Province (grant No. EJG0506–01, B200606 and WC03115) and the Youth Innovation Found­ation of Harbin.

supplementary crystallographic information

Comment

In the past few decades, there has been increased interest in coordination chemistry and biochemistry of oxovanadium. The main reason is that the function of vanadium in biological system has been recognized, such as the regulation of carbohydrate metabolism (Butler & Walker, 1993; Martinez et al., 2001; Sun et al., 1996). Generally, Schiff base is coordinated to vanadium through O and N atoms (Deng et al., 2007), similar to those in the biological systems. Therefore, it is important to intensively study the relationship of syntheses and structural properties of vanadium-schiff base complexes. We report here the crystal structure of the title compound, a vanadium complex with a schiff-base ligand, N,N'-bis(salicylidene)ethylenediamine (H2salen).

In the asymmetric unit, there are two crystallographically independent molecules (Fig. 1). Each VIV atom is coordinated by two N atoms and two O atoms from a salen ligand in the equatorial plane and an oxido O atom in the apical position, resulting in a five-coordinated square-pyramidal geometry (Table 1). The V ?O bond lengths are 1.582 (2) and 1.583 (2) Å, which are in the normal range. In the crystal structure, though each salen ligand contains two phenyl ring with dihedral angles of 156.3 (4)° and 164.1 (4)°, respectively, there are no π–π interactions between the molecules. In virtue of weak intermolecular C—H···O hydrogen bonds (Table 2), a three-dimensional hydrogen-bonding network is constructed (Fig. 2).

Experimental

A mixture of VOSO4.4H2O (1.175 g, 5 mmol), H2salen (0.725 g, 5 mmol), triethylamine (0.20 mmol) and methanol (0.50 mol) in water was stirred for 1 h, and then heated at 413 K for 3 d in a sealed 25 ml Teflon-lined stainless steel vessel under autogenous pressure. After the reaction mixture was slowly cooled to room temperature at a rate of 5 K h-1, black block crystals of the title compound were collected by filtration, washed with distilled water and dried in air.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97Å (CH2) and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A view of the crystal packing. Hydrogen bonds are drawn as dashed lines.

Crystal data

[V(C16H14N2O2)O]F000 = 684
Mr = 333.23Dx = 1.509 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9875 reflections
a = 13.648 (3) Åθ = 3.0–27.5º
b = 6.8085 (14) ŵ = 0.69 mm1
c = 15.952 (3) ÅT = 293 (2) K
β = 98.24 (3)ºBlock, black
V = 1466.9 (5) Å30.32 × 0.21 × 0.11 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer6102 independent reflections
Radiation source: rotating anode4561 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.0º
ω scansh = −17→17
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −8→8
Tmin = 0.809, Tmax = 0.930l = −20→19
14358 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043  w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1081P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max = 0.006
S = 1.03Δρmax = 0.57 e Å3
6102 reflectionsΔρmin = −0.43 e Å3
397 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 2456 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map

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.

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

xyzUiso*/Ueq
V10.27998 (4)0.86758 (8)0.08474 (3)0.04713 (15)
V20.73287 (4)0.88060 (8)0.57991 (3)0.04920 (15)
N10.2175 (2)1.1335 (4)0.04608 (19)0.0488 (7)
N20.3847 (2)1.0619 (4)0.14130 (17)0.0510 (7)
N30.6545 (3)1.1035 (4)0.62647 (19)0.0596 (8)
N40.7996 (3)1.1273 (4)0.5380 (2)0.0683 (9)
O10.2286 (2)0.7938 (4)0.16192 (18)0.0759 (8)
O20.8039 (3)0.7978 (4)0.65914 (19)0.0841 (9)
O30.20463 (17)0.7577 (3)−0.01603 (15)0.0507 (6)
O40.38881 (19)0.7014 (3)0.06653 (15)0.0565 (6)
O50.61179 (19)0.7339 (3)0.56339 (14)0.0555 (6)
O60.7688 (2)0.7514 (4)0.48130 (16)0.0598 (6)
C10.1221 (3)0.8198 (5)−0.0612 (2)0.0455 (8)
C20.0694 (3)0.6938 (6)−0.1214 (2)0.0602 (10)
H20.09340.5679−0.12830.072*
C3−0.0166 (3)0.7526 (7)−0.1700 (3)0.0677 (11)
H3−0.05040.6651−0.20860.081*
C4−0.0541 (3)0.9403 (6)−0.1627 (2)0.0618 (10)
H4−0.11250.9790−0.19590.074*
C5−0.0043 (3)1.0658 (6)−0.1062 (2)0.0565 (9)
H5−0.02921.1917−0.10110.068*
C60.0835 (3)1.0116 (5)−0.0554 (2)0.0465 (8)
C70.1371 (3)1.1600 (5)−0.0042 (2)0.0508 (8)
H70.11111.2865−0.00790.061*
C80.2716 (3)1.3091 (5)0.0809 (2)0.0613 (10)
H8A0.22531.40920.09370.074*
H8B0.31071.36220.04010.074*
C90.3379 (3)1.2495 (5)0.1604 (3)0.0655 (10)
H9A0.38791.34910.17640.079*
H9B0.29961.23240.20670.079*
C100.4778 (3)1.0407 (5)0.1580 (2)0.0556 (9)
H100.51431.14530.18360.067*
C110.5313 (3)0.8654 (7)0.13993 (19)0.0540 (7)
C120.6340 (3)0.8573 (8)0.1668 (2)0.0697 (10)
H120.66570.96540.19420.084*
C130.6879 (3)0.6955 (8)0.1537 (3)0.0760 (13)
H130.75570.69310.17200.091*
C140.6415 (3)0.5350 (7)0.1133 (2)0.0702 (12)
H140.67800.42270.10580.084*
C150.5407 (3)0.5390 (6)0.0837 (2)0.0584 (9)
H150.51090.43090.05490.070*
C160.4833 (3)0.7039 (5)0.0967 (2)0.0515 (8)
C170.5307 (3)0.7501 (5)0.5992 (2)0.0506 (8)
C180.4647 (3)0.5918 (7)0.5952 (2)0.0599 (9)
H180.47900.47740.56750.072*
C190.3798 (3)0.6014 (8)0.6310 (2)0.0695 (11)
H190.33830.49260.62830.083*
C200.3545 (3)0.7698 (8)0.6711 (3)0.0798 (13)
H200.29640.77480.69520.096*
C210.4155 (3)0.9279 (7)0.6749 (2)0.0707 (12)
H210.39751.04270.70040.085*
C220.5057 (3)0.9226 (5)0.6412 (2)0.0561 (9)
C230.5682 (4)1.0928 (6)0.6496 (2)0.0658 (11)
H230.54451.20430.67380.079*
C240.7116 (5)1.2892 (6)0.6381 (3)0.0991 (19)
H24A0.66691.39880.64190.119*
H24B0.75781.28380.69030.119*
C250.7656 (5)1.3167 (7)0.5658 (4)0.119 (2)
H25A0.72261.37860.51960.143*
H25B0.82201.40230.58190.143*
C260.8629 (4)1.1322 (6)0.4880 (3)0.0761 (12)
H260.89541.25070.48280.091*
C270.8889 (3)0.9717 (6)0.4386 (3)0.0642 (11)
C280.9623 (4)0.9992 (9)0.3841 (3)0.0943 (16)
H280.99601.11800.38490.113*
C290.9831 (4)0.8558 (12)0.3318 (3)0.1094 (19)
H291.03100.87640.29670.131*
C300.9342 (4)0.6780 (9)0.3294 (3)0.0943 (16)
H300.94910.57990.29270.113*
C310.8646 (3)0.6461 (7)0.3805 (3)0.0742 (12)
H310.83270.52510.37850.089*
C320.8391 (3)0.7910 (6)0.4364 (2)0.0571 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
V10.0570 (3)0.0332 (2)0.0502 (3)−0.0080 (3)0.0042 (2)−0.0022 (3)
V20.0635 (4)0.0335 (3)0.0486 (3)0.0022 (3)0.0011 (2)−0.0011 (3)
N10.0523 (18)0.0317 (13)0.0634 (17)−0.0046 (11)0.0115 (14)−0.0086 (12)
N20.058 (2)0.0402 (15)0.0517 (15)−0.0092 (13)−0.0015 (14)−0.0046 (13)
N30.086 (3)0.0376 (15)0.0562 (17)−0.0007 (15)0.0125 (17)−0.0066 (13)
N40.070 (2)0.0378 (15)0.099 (3)−0.0036 (14)0.021 (2)−0.0029 (16)
O10.091 (2)0.0718 (18)0.0661 (16)−0.0279 (15)0.0150 (15)0.0010 (13)
O20.107 (2)0.0601 (16)0.0731 (17)0.0166 (16)−0.0276 (17)−0.0025 (14)
O30.0551 (15)0.0352 (11)0.0596 (13)−0.0047 (10)0.0002 (11)−0.0074 (10)
O40.0562 (16)0.0389 (12)0.0703 (15)−0.0014 (11)−0.0049 (12)−0.0058 (12)
O50.0669 (17)0.0444 (13)0.0576 (13)−0.0018 (11)0.0176 (12)−0.0068 (11)
O60.0676 (17)0.0475 (14)0.0673 (15)−0.0011 (12)0.0199 (13)−0.0065 (12)
C10.048 (2)0.0438 (19)0.0456 (16)−0.0060 (13)0.0084 (15)−0.0008 (13)
C20.073 (3)0.048 (2)0.058 (2)−0.0034 (18)0.004 (2)−0.0103 (18)
C30.064 (3)0.077 (3)0.060 (2)−0.013 (2)−0.001 (2)−0.011 (2)
C40.054 (2)0.083 (3)0.0466 (18)0.0014 (19)−0.0004 (16)0.0002 (18)
C50.053 (2)0.062 (2)0.0548 (19)0.0058 (18)0.0100 (17)0.0008 (18)
C60.048 (2)0.0452 (18)0.0482 (17)−0.0047 (14)0.0137 (15)−0.0017 (15)
C70.049 (2)0.0370 (17)0.068 (2)0.0027 (14)0.0119 (18)0.0022 (15)
C80.068 (3)0.0352 (17)0.080 (3)−0.0031 (15)0.007 (2)−0.0101 (16)
C90.076 (3)0.0449 (19)0.073 (2)−0.0094 (18)0.003 (2)−0.0191 (19)
C100.066 (3)0.0445 (19)0.0522 (19)−0.0122 (16)−0.0066 (17)−0.0051 (16)
C110.057 (2)0.0536 (18)0.0494 (15)−0.005 (2)0.0014 (14)0.004 (2)
C120.062 (2)0.087 (3)0.0583 (19)−0.010 (3)0.0032 (17)−0.008 (3)
C130.051 (3)0.115 (4)0.061 (2)0.003 (3)0.0072 (19)0.002 (3)
C140.066 (3)0.093 (3)0.054 (2)0.020 (2)0.017 (2)0.005 (2)
C150.065 (3)0.056 (2)0.0548 (19)0.0054 (18)0.0095 (18)−0.0010 (18)
C160.060 (2)0.0502 (19)0.0432 (17)−0.0002 (16)0.0024 (16)0.0043 (16)
C170.058 (2)0.0517 (19)0.0398 (16)0.0064 (17)−0.0009 (15)0.0057 (15)
C180.060 (3)0.066 (2)0.0493 (19)−0.0012 (19)−0.0042 (17)0.0007 (18)
C190.056 (3)0.090 (3)0.058 (2)−0.010 (2)−0.0083 (19)0.013 (2)
C200.060 (3)0.112 (4)0.067 (2)0.011 (3)0.010 (2)0.024 (3)
C210.075 (3)0.077 (3)0.061 (2)0.026 (2)0.015 (2)0.013 (2)
C220.065 (2)0.058 (2)0.0454 (16)0.0140 (17)0.0061 (16)0.0068 (16)
C230.110 (4)0.0428 (19)0.0494 (19)0.016 (2)0.026 (2)0.0037 (17)
C240.183 (6)0.037 (2)0.085 (3)−0.026 (3)0.045 (4)−0.020 (2)
C250.143 (5)0.051 (3)0.177 (6)−0.023 (3)0.071 (5)−0.035 (3)
C260.073 (3)0.048 (2)0.108 (3)−0.0116 (19)0.013 (3)0.010 (2)
C270.058 (3)0.062 (2)0.073 (3)0.0045 (19)0.010 (2)0.016 (2)
C280.087 (4)0.090 (4)0.111 (4)−0.003 (3)0.032 (3)0.030 (3)
C290.117 (4)0.123 (5)0.101 (3)0.018 (5)0.058 (3)0.015 (4)
C300.108 (4)0.100 (4)0.082 (3)0.008 (3)0.039 (3)0.001 (3)
C310.075 (3)0.076 (3)0.075 (3)0.005 (2)0.023 (2)−0.008 (2)
C320.052 (2)0.059 (2)0.058 (2)0.0048 (17)0.0010 (18)0.0065 (17)

Geometric parameters (Å, °)

V1—O11.584 (3)C10—H100.9300
V1—O41.922 (3)C11—C121.407 (5)
V1—O31.931 (2)C11—C161.408 (5)
V1—N12.058 (3)C12—C131.358 (7)
V1—N22.059 (3)C12—H120.9300
V2—O21.582 (3)C13—C141.376 (7)
V2—O51.917 (3)C13—H130.9300
V2—O61.926 (2)C14—C151.390 (6)
V2—N32.056 (3)C14—H140.9300
V2—N42.067 (3)C15—C161.401 (5)
N1—C71.275 (4)C15—H150.9300
N1—C81.472 (4)C17—C181.401 (5)
N2—C101.268 (5)C17—C221.418 (5)
N2—C91.480 (5)C18—C191.364 (6)
N3—C231.286 (5)C18—H180.9300
N3—C241.482 (5)C19—C201.381 (7)
N4—C261.258 (5)C19—H190.9300
N4—C251.461 (6)C20—C211.357 (7)
O3—C11.316 (4)C20—H200.9300
O4—C161.311 (4)C21—C221.412 (5)
O5—C171.320 (4)C21—H210.9300
O6—C321.305 (5)C22—C231.434 (6)
C1—C21.406 (5)C23—H230.9300
C1—C61.416 (5)C24—C251.468 (6)
C2—C31.370 (6)C24—H24A0.9700
C2—H20.9300C24—H24B0.9700
C3—C41.388 (6)C25—H25A0.9700
C3—H30.9300C25—H25B0.9700
C4—C51.352 (5)C26—C271.422 (6)
C4—H40.9300C26—H260.9300
C5—C61.396 (5)C27—C321.404 (6)
C5—H50.9300C27—C281.429 (6)
C6—C71.433 (5)C28—C291.341 (8)
C7—H70.9300C28—H280.9300
C8—C91.504 (5)C29—C301.380 (9)
C8—H8A0.9700C29—H290.9300
C8—H8B0.9700C30—C311.355 (6)
C9—H9A0.9700C30—H300.9300
C9—H9B0.9700C31—C321.406 (6)
C10—C111.450 (6)C31—H310.9300
O1—V1—O4111.65 (15)C12—C11—C16119.4 (4)
O1—V1—O3106.38 (13)C12—C11—C10118.7 (4)
O4—V1—O388.68 (10)C16—C11—C10121.9 (3)
O1—V1—N1107.53 (15)C13—C12—C11121.5 (5)
O4—V1—N1140.24 (11)C13—C12—H12119.2
O3—V1—N186.73 (11)C11—C12—H12119.2
O1—V1—N2102.72 (13)C12—C13—C14119.6 (4)
O4—V1—N286.65 (11)C12—C13—H13120.2
O3—V1—N2150.17 (11)C14—C13—H13120.2
N1—V1—N278.34 (12)C13—C14—C15120.7 (4)
O2—V2—O5109.95 (15)C13—C14—H14119.7
O2—V2—O6106.92 (15)C15—C14—H14119.7
O5—V2—O688.01 (11)C14—C15—C16120.8 (4)
O2—V2—N3105.39 (15)C14—C15—H15119.6
O5—V2—N387.24 (12)C16—C15—H15119.6
O6—V2—N3147.00 (12)O4—C16—C15118.5 (3)
O2—V2—N4107.48 (17)O4—C16—C11123.6 (3)
O5—V2—N4142.21 (13)C15—C16—C11117.9 (3)
O6—V2—N486.06 (13)O5—C17—C18119.3 (3)
N3—V2—N478.04 (14)O5—C17—C22123.2 (3)
C7—N1—C8117.5 (3)C18—C17—C22117.5 (3)
C7—N1—V1126.5 (2)C19—C18—C17121.6 (4)
C8—N1—V1115.9 (2)C19—C18—H18119.2
C10—N2—C9120.3 (3)C17—C18—H18119.2
C10—N2—V1129.1 (2)C18—C19—C20121.2 (5)
C9—N2—V1110.6 (2)C18—C19—H19119.4
C23—N3—C24119.9 (4)C20—C19—H19119.4
C23—N3—V2127.4 (3)C21—C20—C19119.1 (4)
C24—N3—V2112.6 (3)C21—C20—H20120.4
C26—N4—C25116.5 (4)C19—C20—H20120.4
C26—N4—V2127.0 (3)C20—C21—C22121.7 (4)
C25—N4—V2116.5 (3)C20—C21—H21119.2
C1—O3—V1130.0 (2)C22—C21—H21119.2
C16—O4—V1132.7 (2)C21—C22—C17118.9 (4)
C17—O5—V2131.0 (2)C21—C22—C23118.9 (4)
C32—O6—V2130.3 (2)C17—C22—C23122.2 (4)
O3—C1—C2119.4 (3)N3—C23—C22125.2 (4)
O3—C1—C6123.9 (3)N3—C23—H23117.4
C2—C1—C6116.6 (3)C22—C23—H23117.4
C3—C2—C1121.4 (4)C25—C24—N3108.9 (4)
C3—C2—H2119.3C25—C24—H24A109.9
C1—C2—H2119.3N3—C24—H24A109.9
C2—C3—C4121.2 (4)C25—C24—H24B109.9
C2—C3—H3119.4N3—C24—H24B109.9
C4—C3—H3119.4H24A—C24—H24B108.3
C5—C4—C3118.8 (4)N4—C25—C24110.1 (4)
C5—C4—H4120.6N4—C25—H25A109.6
C3—C4—H4120.6C24—C25—H25A109.6
C4—C5—C6121.8 (4)N4—C25—H25B109.6
C4—C5—H5119.1C24—C25—H25B109.6
C6—C5—H5119.1H25A—C25—H25B108.2
C5—C6—C1120.2 (3)N4—C26—C27125.5 (4)
C5—C6—C7118.1 (3)N4—C26—H26117.3
C1—C6—C7121.5 (3)C27—C26—H26117.3
N1—C7—C6125.6 (3)C32—C27—C26121.9 (4)
N1—C7—H7117.2C32—C27—C28118.6 (4)
C6—C7—H7117.2C26—C27—C28119.3 (4)
N1—C8—C9108.0 (3)C29—C28—C27120.8 (5)
N1—C8—H8A110.1C29—C28—H28119.6
C9—C8—H8A110.1C27—C28—H28119.6
N1—C8—H8B110.1C28—C29—C30120.8 (5)
C9—C8—H8B110.1C28—C29—H29119.6
H8A—C8—H8B108.4C30—C29—H29119.6
N2—C9—C8106.5 (3)C31—C30—C29120.1 (5)
N2—C9—H9A110.4C31—C30—H30119.9
C8—C9—H9A110.4C29—C30—H30119.9
N2—C9—H9B110.4C30—C31—C32121.8 (5)
C8—C9—H9B110.4C30—C31—H31119.1
H9A—C9—H9B108.6C32—C31—H31119.1
N2—C10—C11124.8 (3)O6—C32—C27124.0 (4)
N2—C10—H10117.6O6—C32—C31118.1 (4)
C11—C10—H10117.6C27—C32—C31117.9 (4)
O1—V1—N1—C7−83.8 (3)C5—C6—C7—N1179.1 (3)
O4—V1—N1—C7106.3 (3)C1—C6—C7—N1−6.8 (5)
O3—V1—N1—C722.3 (3)C7—N1—C8—C9158.5 (3)
N2—V1—N1—C7176.4 (3)V1—N1—C8—C9−21.1 (4)
O1—V1—N1—C895.8 (3)C10—N2—C9—C8129.6 (4)
O4—V1—N1—C8−74.1 (3)V1—N2—C9—C8−48.7 (4)
O3—V1—N1—C8−158.1 (3)N1—C8—C9—N243.8 (4)
N2—V1—N1—C8−4.1 (3)C9—N2—C10—C11−178.4 (3)
O1—V1—N2—C10105.6 (3)V1—N2—C10—C11−0.5 (5)
O4—V1—N2—C10−5.8 (3)N2—C10—C11—C12−175.9 (3)
O3—V1—N2—C10−87.3 (4)N2—C10—C11—C163.8 (6)
N1—V1—N2—C10−148.8 (3)C16—C11—C12—C13−1.4 (6)
O1—V1—N2—C9−76.3 (3)C10—C11—C12—C13178.4 (4)
O4—V1—N2—C9172.3 (2)C11—C12—C13—C140.0 (6)
O3—V1—N2—C990.8 (3)C12—C13—C14—C151.8 (6)
N1—V1—N2—C929.3 (2)C13—C14—C15—C16−2.1 (6)
O2—V2—N3—C23−95.3 (4)V1—O4—C16—C15167.7 (2)
O5—V2—N3—C2314.7 (3)V1—O4—C16—C11−14.0 (5)
O6—V2—N3—C2396.7 (4)C14—C15—C16—O4179.1 (3)
N4—V2—N3—C23159.6 (4)C14—C15—C16—C110.6 (5)
O2—V2—N3—C2480.4 (3)C12—C11—C16—O4−177.2 (3)
O5—V2—N3—C24−169.7 (3)C10—C11—C16—O43.0 (5)
O6—V2—N3—C24−87.6 (4)C12—C11—C16—C151.1 (5)
N4—V2—N3—C24−24.7 (3)C10—C11—C16—C15−178.7 (3)
O2—V2—N4—C2685.3 (4)V2—O5—C17—C18−161.2 (2)
O5—V2—N4—C26−102.8 (4)V2—O5—C17—C2219.7 (5)
O6—V2—N4—C26−21.2 (4)O5—C17—C18—C19−179.8 (3)
N3—V2—N4—C26−172.1 (4)C22—C17—C18—C19−0.7 (5)
O2—V2—N4—C25−98.3 (4)C17—C18—C19—C201.4 (6)
O5—V2—N4—C2573.6 (5)C18—C19—C20—C21−0.1 (6)
O6—V2—N4—C25155.2 (4)C19—C20—C21—C22−2.0 (6)
N3—V2—N4—C254.3 (4)C20—C21—C22—C172.7 (5)
O1—V1—O3—C182.7 (3)C20—C21—C22—C23−178.1 (4)
O4—V1—O3—C1−165.1 (3)O5—C17—C22—C21177.8 (3)
N1—V1—O3—C1−24.6 (3)C18—C17—C22—C21−1.3 (5)
N2—V1—O3—C1−84.2 (3)O5—C17—C22—C23−1.4 (5)
O1—V1—O4—C16−89.2 (3)C18—C17—C22—C23179.5 (3)
O3—V1—O4—C16163.7 (3)C24—N3—C23—C22179.5 (4)
N1—V1—O4—C1680.4 (3)V2—N3—C23—C22−5.1 (6)
N2—V1—O4—C1613.2 (3)C21—C22—C23—N3175.6 (4)
O2—V2—O5—C1783.2 (3)C17—C22—C23—N3−5.2 (6)
O6—V2—O5—C17−169.5 (3)C23—N3—C24—C25−143.1 (5)
N3—V2—O5—C17−22.2 (3)V2—N3—C24—C2540.9 (6)
N4—V2—O5—C17−88.6 (3)C26—N4—C25—C24−166.5 (5)
O2—V2—O6—C32−82.8 (3)V2—N4—C25—C2416.8 (7)
O5—V2—O6—C32166.9 (3)N3—C24—C25—N4−36.1 (7)
N3—V2—O6—C3285.1 (4)C25—N4—C26—C27−164.8 (5)
N4—V2—O6—C3224.2 (3)V2—N4—C26—C2711.6 (7)
V1—O3—C1—C2−166.4 (2)N4—C26—C27—C325.1 (7)
V1—O3—C1—C616.0 (5)N4—C26—C27—C28179.8 (5)
O3—C1—C2—C3−179.7 (4)C32—C27—C28—C290.1 (8)
C6—C1—C2—C3−1.9 (5)C26—C27—C28—C29−174.8 (5)
C1—C2—C3—C41.1 (7)C27—C28—C29—C30−0.1 (9)
C2—C3—C4—C5−0.1 (6)C28—C29—C30—C31−0.3 (10)
C3—C4—C5—C60.0 (6)C29—C30—C31—C320.6 (8)
C4—C5—C6—C1−0.9 (5)V2—O6—C32—C27−17.4 (5)
C4—C5—C6—C7173.3 (3)V2—O6—C32—C31164.6 (3)
O3—C1—C6—C5179.5 (3)C26—C27—C32—O6−3.1 (6)
C2—C1—C6—C51.8 (5)C28—C27—C32—O6−177.8 (4)
O3—C1—C6—C75.5 (5)C26—C27—C32—C31174.9 (4)
C2—C1—C6—C7−172.1 (3)C28—C27—C32—C310.1 (6)
C8—N1—C7—C6168.6 (3)C30—C31—C32—O6177.6 (4)
V1—N1—C7—C6−11.8 (5)C30—C31—C32—C27−0.5 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8B···O4i0.972.553.139 (3)119
C14—H14···O3ii0.932.563.364 (3)145
C24—H24B···O1iii0.972.343.178 (3)144

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2124).

References

  • Butler, A. & Walker, J. V. (1993). Chem. Rev.93, 1937–1944.
  • Deng, Z. P., Gao, S., Zhao, H. & Huo, L. H. (2007). Chin. J. Inorg. Chem.23, 173–176.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Martinez, J. S., Carroll, G. L., Tschirret-Guth, R. A., Altenhoff, G., Little, R. D. & Butler, A. (2001). J. Am. Chem. Soc.123, 3289–3294. [PubMed]
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, Y., James, B. R., Rettig, S. J. & Orvig, C. (1996). Inorg. Chem.35, 1667–1673. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography