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The title compound, [VO(C9H6NO)2(C3H7O)], contains a six-coordinate VV atom. The central VV atom has a distorted octahedral coordination geometry involving two O atoms of the oxo (V=O) and propoxo (V-OnPr) groups, two N and two O atoms of the two 8-hydroxy­quinoline rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002295/cv6084sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002295/cv6084Isup2.hkl
Contains datablock I

CCDC reference: 182571

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • H-atom completeness 85%
  • R factor = 0.053
  • wR factor = 0.176
  • Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_213 Alert C Atom C2P has ADP max/min Ratio ........... 3.10 prolate PLAT_320 Alert C Check Hybridisation of C2P in main residue ? PLAT_320 Alert C Check Hybridisation of C3P in main residue ? General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C21 H19 N2 O4 V1 Atom count from the _atom_site data: C21 H16 N2 O4 V1 CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C21 H19 N2 O4 V TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 42.00 42.00 0.00 H 38.00 32.00 6.00 N 4.00 4.00 0.00 O 8.00 8.00 0.00 V 2.00 2.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

8-Hydroxyquinoline (8-quinolinol, oxine) is a well known analytical reagent for forming chelate complexes with metal ions. Its metal complexes with copper(II), zinc(II) or nickel(II) have remarkable antimicrobial or fungicidal activity (Okide et al., 2000; Patel et al., 1999). The bismuth(III) complex also has antitumor activity against leukaemia (Smith et al., 1998). On the other hand, vanadium(IV) and vanadium(V) salts have the insulin-mimetic effects in living animals (Bhattacharyya & Tracey, 2001) or in intact cell systems (Kanamori et al., 2001). Peroxovanadium(V) complexes also show antitumor activity (Djordjevic & Wampler, 1985). These findings need to drive the structural research of various 8-hydroxyquinoline derivatives, as well as vanadium compounds because of their therapeutic value. For these reasons, we aimed to prepare the hybridized compounds of 8-hydroxyquinoline and vanadium, and determine the structure.

Here, we have determined the vanadium(V) complex of 8-hydroxyquinoline, (I). The molecular structure of (I) is shown in Fig. 1. The crystal structures of similar vanadium(V) compounds have been reported, e.g. as the isopropyl ester, oxoisopropoxobis(8-hydroxyquinolinato)vanadium(V) with the VO(OiPr) group (Scheidt, 1973), and as the ethyl ester, oxoetoxobis(5,7-dichloro-8-hydroxquinolinato)vanadium(V) with the VO(OEt) group (González-Baró et al., 1998). These species are considered as inorganic esters (Baran, 2000). Both of the above ester compounds were prepared by the esterification of the oxohydroxobis(8-hydroxyqinolinato)vanadium(V) and oxohydroxobis(5,7-dichloro-8-hydroxyquinolinato)vanadium(V).

While the title compound was obtained directly from the crystallizing mixtures of 8-hydroxyquinoline, VOSO4 and normal propanol. The O atoms of the oxo (VO) and propoxo (V—OnPr) groups are in the cis configuration with respect to the VO(OnPr) group. Two N atoms of the 8-hydroxyquinoline molecules are located in mutual cis positions, but two O atoms at 8-position are trans. The central VV atom has a distorted octahedral coordination geometry. The overall atomic arrangement of the title compound is the same as that of oxoisopropoxo(8-hydroxyquinolinato)vanadium(V) (Scheidt, 1973), although small differences are present in their geometrical parameters.

Experimental top

A dark-brown plate crystal of (I) was obtained by slow evapolation from a propanol solution of a mixture of 8-hydroxyquinoline and VOSO4 (8:1).

Refinement top

All H atoms, except those attached to C3P, were checked their presence in difference Fourier maps, and after that they were fixed at ideal positions and included in the refinement.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Displacement ellipsoids for non-H atoms correspond to 50% probability.
(I) top
Crystal data top
C21H19N2O4VZ = 2
Mr = 414.33F(000) = 422.0
Triclinic, P1Dx = 1.442 Mg m3
a = 9.639 (3) ÅMo Kα radiation, λ = 0.7107 Å
b = 12.751 (3) ÅCell parameters from 25 reflections
c = 9.044 (3) Åθ = 14.7–15.0°
α = 95.76 (2)°µ = 0.55 mm1
β = 110.97 (2)°T = 296 K
γ = 108.63 (2)°Hexagonal, dark brown
V = 954.1 (5) Å30.20 × 0.20 × 0.07 mm
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.018
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 012
Tmin = 0.896, Tmax = 0.962k = 1615
4645 measured reflectionsl = 1110
4391 independent reflections3 standard reflections every 150 reflections
2952 reflections with I > 2σ(I) intensity decay: 0.6%
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.176(Δ/σ)max = 0.002
S = 1.14Δρmax = 0.64 e Å3
4389 reflectionsΔρmin = 0.43 e Å3
253 parameters
Crystal data top
C21H19N2O4Vγ = 108.63 (2)°
Mr = 414.33V = 954.1 (5) Å3
Triclinic, P1Z = 2
a = 9.639 (3) ÅMo Kα radiation
b = 12.751 (3) ŵ = 0.55 mm1
c = 9.044 (3) ÅT = 296 K
α = 95.76 (2)°0.20 × 0.20 × 0.07 mm
β = 110.97 (2)°
Data collection top
Rigaku AFC-5R
diffractometer
2952 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.018
Tmin = 0.896, Tmax = 0.9623 standard reflections every 150 reflections
4645 measured reflections intensity decay: 0.6%
4391 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053253 parameters
wR(F2) = 0.176H-atom parameters not refined
S = 1.14Δρmax = 0.64 e Å3
4389 reflectionsΔρmin = 0.43 e Å3
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted

R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V(1)0.63027 (6)0.26595 (4)0.03618 (7)0.0384 (2)
O(1A)0.7176 (3)0.1585 (2)0.1250 (3)0.0420 (5)
O(1B)0.5153 (3)0.3619 (2)0.0301 (3)0.0424 (5)
O(1V)0.7766 (3)0.3553 (2)0.0133 (3)0.0513 (6)
O(2V)0.5153 (3)0.1735 (2)0.1621 (3)0.0477 (5)
N(1A)0.7414 (3)0.3407 (2)0.3017 (3)0.0414 (6)
N(1B)0.4235 (3)0.1651 (2)0.1012 (3)0.0376 (5)
C(1A)0.7531 (5)0.4364 (3)0.3848 (5)0.0537 (9)
C(1B)0.3814 (4)0.0644 (3)0.1350 (4)0.0447 (7)
C(1P)0.5377 (6)0.1806 (4)0.3083 (5)0.069 (1)
C(2A)0.8324 (6)0.4703 (3)0.5566 (5)0.067 (1)
C(2B)0.2457 (5)0.0203 (3)0.1678 (5)0.0570 (9)
C(2P)0.451 (1)0.242 (1)0.4067 (9)0.172 (4)
C(3A)0.8964 (5)0.4039 (4)0.6399 (5)0.064 (1)
C(3B)0.1516 (4)0.0814 (3)0.1641 (5)0.0544 (9)
C(3P)0.359 (1)0.290 (1)0.3968 (10)0.198 (5)
C(4A)0.8850 (4)0.2985 (3)0.5575 (4)0.0528 (8)
C(4B)0.1900 (4)0.1885 (3)0.1256 (4)0.0420 (7)
C(5A)0.9409 (5)0.2195 (4)0.6288 (5)0.067 (1)
C(5B)0.1016 (4)0.2598 (3)0.1144 (4)0.0485 (8)
C(6A)0.9165 (6)0.1193 (4)0.5320 (5)0.067 (1)
C(6B)0.1538 (4)0.3620 (3)0.0769 (4)0.0474 (8)
C(7A)0.8397 (5)0.0938 (3)0.3601 (5)0.0546 (9)
C(7B)0.2949 (4)0.4008 (3)0.0493 (4)0.0432 (7)
C(8A)0.7871 (4)0.1714 (3)0.2853 (4)0.0402 (7)
C(8B)0.3822 (4)0.3333 (2)0.0578 (4)0.0369 (6)
C(9A)0.8063 (4)0.2728 (3)0.3860 (4)0.0410 (7)
C(9B)0.3295 (4)0.2263 (2)0.0956 (4)0.0355 (6)
H(1A)0.70480.48530.32810.0558*
H(1B)0.44610.02130.14070.0455*
H(1PA)0.65110.21840.27950.0847*
H(1PB)0.50390.10470.37090.0847*
H(2A)0.84150.54360.61550.0701*
H(2B)0.21370.05280.19340.0539*
H(2PA)0.53590.29930.42110.2038*
H(2PB)0.38780.18580.51080.2038*
H(3A)0.94940.42620.76070.0667*
H(3B)0.05800.04900.18440.0531*
H(5A)0.99250.23260.74580.0648*
H(5B)0.00510.23540.13180.0449*
H(6A)0.95600.06880.58490.0700*
H(6B)0.09100.40850.06950.0487*
H(7A)0.82380.02250.29570.0564*
H(7B)0.32870.47460.02630.0413*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V(1)0.0401 (3)0.0384 (3)0.0454 (3)0.0196 (2)0.0222 (2)0.0141 (2)
O(1A)0.048 (1)0.042 (1)0.042 (1)0.0258 (10)0.018 (1)0.0094 (9)
O(1B)0.041 (1)0.037 (1)0.063 (1)0.0205 (9)0.029 (1)0.022 (1)
O(1V)0.044 (1)0.053 (1)0.070 (2)0.021 (1)0.034 (1)0.026 (1)
O(2V)0.056 (1)0.051 (1)0.042 (1)0.027 (1)0.020 (1)0.012 (1)
N(1A)0.040 (1)0.034 (1)0.047 (2)0.013 (1)0.018 (1)0.005 (1)
N(1B)0.041 (1)0.033 (1)0.041 (1)0.015 (1)0.018 (1)0.009 (1)
C(1A)0.058 (2)0.040 (2)0.061 (2)0.018 (2)0.024 (2)0.004 (2)
C(1B)0.053 (2)0.035 (2)0.049 (2)0.016 (1)0.023 (2)0.012 (1)
C(1P)0.095 (3)0.084 (3)0.054 (2)0.049 (3)0.043 (2)0.025 (2)
C(2A)0.078 (3)0.052 (2)0.062 (2)0.019 (2)0.031 (2)0.006 (2)
C(2B)0.059 (2)0.045 (2)0.069 (2)0.014 (2)0.031 (2)0.024 (2)
C(2P)0.187 (8)0.34 (1)0.100 (5)0.179 (9)0.090 (6)0.146 (7)
C(3A)0.067 (2)0.065 (2)0.046 (2)0.013 (2)0.022 (2)0.000 (2)
C(3B)0.048 (2)0.052 (2)0.063 (2)0.008 (2)0.031 (2)0.019 (2)
C(3P)0.30 (1)0.31 (1)0.098 (5)0.27 (1)0.070 (7)0.074 (7)
C(4A)0.049 (2)0.058 (2)0.045 (2)0.013 (2)0.019 (2)0.007 (2)
C(4B)0.037 (2)0.046 (2)0.039 (2)0.013 (1)0.016 (1)0.007 (1)
C(5A)0.071 (3)0.083 (3)0.049 (2)0.034 (2)0.021 (2)0.027 (2)
C(5B)0.039 (2)0.063 (2)0.051 (2)0.022 (2)0.025 (2)0.012 (2)
C(6A)0.079 (3)0.078 (3)0.060 (2)0.045 (2)0.026 (2)0.036 (2)
C(6B)0.044 (2)0.058 (2)0.046 (2)0.030 (2)0.017 (1)0.007 (1)
C(7A)0.064 (2)0.056 (2)0.056 (2)0.034 (2)0.026 (2)0.022 (2)
C(7B)0.048 (2)0.041 (2)0.048 (2)0.025 (1)0.021 (1)0.013 (1)
C(8A)0.039 (2)0.044 (2)0.044 (2)0.019 (1)0.020 (1)0.013 (1)
C(8B)0.039 (2)0.034 (1)0.039 (2)0.015 (1)0.018 (1)0.009 (1)
C(9A)0.038 (2)0.038 (2)0.044 (2)0.010 (1)0.018 (1)0.008 (1)
C(9B)0.036 (1)0.036 (1)0.033 (1)0.013 (1)0.014 (1)0.007 (1)
Geometric parameters (Å, º) top
V(1)—O(1A)1.924 (3)C(2P)—H(2PA)0.966
V(1)—O(1B)1.888 (3)C(2P)—H(2PB)0.973
V(1)—O(1V)1.600 (3)C(3A)—C(4A)1.421 (7)
V(1)—O(2V)1.775 (2)C(3A)—H(3A)0.990
V(1)—N(1A)2.207 (3)C(3B)—C(4B)1.409 (5)
V(1)—N(1B)2.307 (3)C(3B)—H(3B)0.956
O(1A)—C(8A)1.328 (4)C(4A)—C(5A)1.396 (7)
O(1B)—C(8B)1.338 (5)C(4A)—C(9A)1.409 (5)
O(2V)—C(1P)1.420 (6)C(4B)—C(5B)1.419 (6)
N(1A)—C(1A)1.317 (5)C(4B)—C(9B)1.410 (5)
N(1A)—C(9A)1.363 (5)C(5A)—C(6A)1.375 (7)
N(1B)—C(1B)1.319 (4)C(5A)—H(5A)0.964
N(1B)—C(9B)1.364 (5)C(5B)—C(6B)1.363 (6)
C(1A)—C(2A)1.411 (6)C(5B)—H(5B)0.958
C(1A)—H(1A)0.973C(6A)—C(7A)1.411 (6)
C(1B)—C(2B)1.399 (6)C(6A)—H(6A)0.936
C(1B)—H(1B)0.947C(6B)—C(7B)1.412 (6)
C(1P)—C(2P)1.46 (1)C(6B)—H(6B)0.965
C(1P)—H(1PA)0.965C(7A)—C(8A)1.379 (6)
C(1P)—H(1PB)0.960C(7A)—H(7A)0.964
C(2A)—C(3A)1.339 (7)C(7B)—C(8B)1.373 (6)
C(2A)—H(2A)0.990C(7B)—H(7B)0.963
C(2B)—C(3B)1.365 (7)C(8A)—C(9A)1.424 (5)
C(2B)—H(2B)0.964C(8B)—C(9B)1.418 (4)
C(2P)—C(3P)1.26 (2)
O(1A)···C(1B)i3.137 (4)O(1V)···C(7B)iii3.451 (5)
O(1A)···C(2B)i3.509 (6)O(1V)···C(5B)ii3.570 (5)
O(1A)···C(5B)ii3.551 (5)O(2V)···C(1B)i3.488 (5)
O(1B)···C(7B)iii3.295 (4)C(1A)···C(3A)iv3.442 (6)
O(1V)···C(6B)ii3.443 (5)C(3B)···C(3B)v3.215 (6)
O(1A)—V(1)—O(1B)153.0 (1)C(3P)—C(2P)—H(2PA)104.8
O(1A)—V(1)—O(1V)103.0 (1)C(3P)—C(2P)—H(2PB)103.4
O(1A)—V(1)—O(2V)93.7 (1)H(2PA)—C(2P)—H(2PB)106.3
O(1A)—V(1)—N(1A)76.9 (1)C(2A)—C(3A)—C(4A)120.9 (4)
O(1A)—V(1)—N(1B)82.1 (1)C(2A)—C(3A)—H(3A)120.4
O(1B)—V(1)—O(1V)96.2 (1)C(4A)—C(3A)—H(3A)118.7
O(1B)—V(1)—O(2V)100.6 (1)C(2B)—C(3B)—C(4B)120.1 (4)
O(1B)—V(1)—N(1A)83.8 (1)C(2B)—C(3B)—H(3B)118.8
O(1B)—V(1)—N(1B)76.2 (1)C(4B)—C(3B)—H(3B)121.0
O(1V)—V(1)—O(2V)102.1 (1)C(3A)—C(4A)—C(5A)126.9 (4)
O(1V)—V(1)—N(1A)91.7 (1)C(3A)—C(4A)—C(9A)114.9 (4)
O(1V)—V(1)—N(1B)169.6 (1)C(5A)—C(4A)—C(9A)118.1 (4)
O(2V)—V(1)—N(1A)164.8 (1)C(3B)—C(4B)—C(5B)126.1 (4)
O(2V)—V(1)—N(1B)86.4 (1)C(3B)—C(4B)—C(9B)115.8 (4)
N(1A)—V(1)—N(1B)80.52 (10)C(5B)—C(4B)—C(9B)118.1 (3)
V(1)—O(1A)—C(8A)120.8 (2)C(4A)—C(5A)—C(6A)119.9 (4)
V(1)—O(1B)—C(8B)123.0 (2)C(4A)—C(5A)—H(5A)120.9
V(1)—O(2V)—C(1P)129.7 (2)C(6A)—C(5A)—H(5A)119.2
V(1)—N(1A)—C(1A)130.5 (3)C(4B)—C(5B)—C(6B)119.7 (4)
V(1)—N(1A)—C(9A)111.2 (2)C(4B)—C(5B)—H(5B)119.8
C(1A)—N(1A)—C(9A)118.3 (3)C(6B)—C(5B)—H(5B)120.5
V(1)—N(1B)—C(1B)132.9 (3)C(5A)—C(6A)—C(7A)122.2 (5)
V(1)—N(1B)—C(9B)108.5 (2)C(5A)—C(6A)—H(6A)117.0
C(1B)—N(1B)—C(9B)118.5 (3)C(7A)—C(6A)—H(6A)120.8
N(1A)—C(1A)—C(2A)121.7 (4)C(5B)—C(6B)—C(7B)122.3 (4)
N(1A)—C(1A)—H(1A)120.1C(5B)—C(6B)—H(6B)117.9
C(2A)—C(1A)—H(1A)118.1C(7B)—C(6B)—H(6B)119.9
N(1B)—C(1B)—C(2B)121.9 (4)C(6A)—C(7A)—C(8A)119.5 (4)
N(1B)—C(1B)—H(1B)119.6C(6A)—C(7A)—H(7A)120.1
C(2B)—C(1B)—H(1B)118.5C(8A)—C(7A)—H(7A)120.4
O(2V)—C(1P)—C(2P)113.4 (6)C(6B)—C(7B)—C(8B)119.5 (3)
O(2V)—C(1P)—H(1PA)108.3C(6B)—C(7B)—H(7B)119.3
O(2V)—C(1P)—H(1PB)108.6C(8B)—C(7B)—H(7B)121.3
C(2P)—C(1P)—H(1PA)109.2O(1A)—C(8A)—C(7A)125.0 (3)
C(2P)—C(1P)—H(1PB)109.8O(1A)—C(8A)—C(9A)116.8 (3)
H(1PA)—C(1P)—H(1PB)107.4C(7A)—C(8A)—C(9A)118.2 (3)
C(1A)—C(2A)—C(3A)120.1 (4)O(1B)—C(8B)—C(7B)123.6 (3)
C(1A)—C(2A)—H(2A)119.8O(1B)—C(8B)—C(9B)117.2 (3)
C(3A)—C(2A)—H(2A)120.0C(7B)—C(8B)—C(9B)119.2 (3)
C(1B)—C(2B)—C(3B)120.1 (4)N(1A)—C(9A)—C(4A)124.0 (3)
C(1B)—C(2B)—H(2B)123.0N(1A)—C(9A)—C(8A)114.0 (3)
C(3B)—C(2B)—H(2B)117.0C(4A)—C(9A)—C(8A)122.0 (3)
C(1P)—C(2P)—C(3P)136.3 (9)N(1B)—C(9B)—C(4B)123.6 (3)
C(1P)—C(2P)—H(2PA)102.0N(1B)—C(9B)—C(8B)115.1 (3)
C(1P)—C(2P)—H(2PB)101.4C(4B)—C(9B)—C(8B)121.3 (3)
V(1)—O(1A)—C(8A)—C(7A)173.7 (3)N(1B)—C(9B)—C(8B)—C(7B)179.9 (3)
V(1)—O(1A)—C(8A)—C(9A)5.5 (4)C(1A)—N(1A)—C(9A)—C(4A)0.2 (5)
V(1)—O(1B)—C(8B)—C(7B)178.1 (2)C(1A)—N(1A)—C(9A)—C(8A)179.9 (3)
V(1)—O(1B)—C(8B)—C(9B)1.0 (3)C(1A)—C(2A)—C(3A)—C(4A)0.4 (8)
V(1)—O(2V)—C(1P)—C(2P)91.6 (5)C(1A)—C(2A)—C(3A)—H(3A)178.2
V(1)—O(2V)—C(1P)—H(1PA)29.7C(1B)—N(1B)—C(9B)—C(4B)0.7 (4)
V(1)—O(2V)—C(1P)—H(1PB)146.1C(1B)—N(1B)—C(9B)—C(8B)179.7 (3)
V(1)—N(1A)—C(1A)—C(2A)178.9 (3)C(1B)—C(2B)—C(3B)—C(4B)0.6 (5)
V(1)—N(1A)—C(1A)—H(1A)2.1C(1B)—C(2B)—C(3B)—H(3B)178.6
V(1)—N(1A)—C(9A)—C(4A)179.9 (3)C(2A)—C(1A)—N(1A)—C(9A)1.0 (6)
V(1)—N(1A)—C(9A)—C(8A)0.2 (4)C(2A)—C(3A)—C(4A)—C(5A)177.6 (5)
V(1)—N(1B)—C(1B)—C(2B)178.6 (2)C(2A)—C(3A)—C(4A)—C(9A)1.4 (7)
V(1)—N(1B)—C(1B)—H(1B)3.4C(2B)—C(1B)—N(1B)—C(9B)1.2 (4)
V(1)—N(1B)—C(9B)—C(4B)178.7 (2)C(2B)—C(3B)—C(4B)—C(5B)178.7 (3)
V(1)—N(1B)—C(9B)—C(8B)1.7 (3)C(2B)—C(3B)—C(4B)—C(9B)1.1 (5)
O(1A)—V(1)—O(1B)—C(8B)38.7 (3)C(3A)—C(2A)—C(1A)—H(1A)178.0
O(1A)—V(1)—O(2V)—C(1P)108.7 (4)C(3A)—C(4A)—C(5A)—C(6A)178.2 (5)
O(1A)—V(1)—N(1A)—C(1A)178.0 (4)C(3A)—C(4A)—C(5A)—H(5A)0.8
O(1A)—V(1)—N(1A)—C(9A)1.9 (2)C(3A)—C(4A)—C(9A)—C(8A)179.0 (4)
O(1A)—V(1)—N(1B)—C(1B)16.9 (3)C(3B)—C(2B)—C(1B)—H(1B)178.6
O(1A)—V(1)—N(1B)—C(9B)165.6 (2)C(3B)—C(4B)—C(5B)—C(6B)179.6 (3)
O(1A)—C(8A)—C(7A)—C(6A)178.0 (4)C(3B)—C(4B)—C(5B)—H(5B)1.2
O(1A)—C(8A)—C(7A)—H(7A)2.3C(3B)—C(4B)—C(9B)—C(8B)179.1 (3)
O(1A)—C(8A)—C(9A)—N(1A)3.4 (5)C(3P)—C(2P)—C(1P)—H(1PA)121.8
O(1A)—C(8A)—C(9A)—C(4A)177.0 (3)C(3P)—C(2P)—C(1P)—H(1PB)120.7
O(1B)—V(1)—O(1A)—C(8A)41.6 (3)C(4A)—C(3A)—C(2A)—H(2A)179.8
O(1B)—V(1)—O(2V)—C(1P)94.2 (4)C(4A)—C(5A)—C(6A)—C(7A)1.7 (8)
O(1B)—V(1)—N(1A)—C(1A)21.0 (3)C(4A)—C(5A)—C(6A)—H(6A)180.0
O(1B)—V(1)—N(1A)—C(9A)159.1 (2)C(4A)—C(9A)—C(8A)—C(7A)3.8 (5)
O(1B)—V(1)—N(1B)—C(1B)179.3 (3)C(4B)—C(3B)—C(2B)—H(2B)179.3
O(1B)—V(1)—N(1B)—C(9B)1.7 (2)C(4B)—C(5B)—C(6B)—C(7B)0.4 (5)
O(1B)—C(8B)—C(7B)—C(6B)178.5 (3)C(4B)—C(5B)—C(6B)—H(6B)179.7
O(1B)—C(8B)—C(7B)—H(7B)2.3C(4B)—C(9B)—C(8B)—C(7B)0.4 (4)
O(1B)—C(8B)—C(9B)—N(1B)0.8 (4)C(5A)—C(4A)—C(3A)—H(3A)0.3
O(1B)—C(8B)—C(9B)—C(4B)179.6 (2)C(5A)—C(4A)—C(9A)—C(8A)1.9 (6)
O(1V)—V(1)—O(1A)—C(8A)92.7 (3)C(5A)—C(6A)—C(7A)—C(8A)0.2 (7)
O(1V)—V(1)—O(1B)—C(8B)174.3 (2)C(5A)—C(6A)—C(7A)—H(7A)179.6
O(1V)—V(1)—O(2V)—C(1P)4.6 (4)C(5B)—C(4B)—C(3B)—H(3B)0.9
O(1V)—V(1)—N(1A)—C(1A)75.1 (4)C(5B)—C(4B)—C(9B)—C(8B)1.0 (4)
O(1V)—V(1)—N(1A)—C(9A)104.8 (3)C(5B)—C(6B)—C(7B)—C(8B)1.0 (5)
O(1V)—V(1)—N(1B)—C(1B)137.0 (6)C(5B)—C(6B)—C(7B)—H(7B)178.2
O(1V)—V(1)—N(1B)—C(9B)45.4 (7)C(6A)—C(5A)—C(4A)—C(9A)0.8 (7)
O(2V)—V(1)—O(1A)—C(8A)163.9 (3)C(6A)—C(7A)—C(8A)—C(9A)2.8 (6)
O(2V)—V(1)—O(1B)—C(8B)82.1 (2)C(6B)—C(5B)—C(4B)—C(9B)0.6 (4)
O(2V)—V(1)—N(1A)—C(1A)128.9 (5)C(6B)—C(7B)—C(8B)—C(9B)0.5 (4)
O(2V)—V(1)—N(1A)—C(9A)51.2 (6)C(7A)—C(6A)—C(5A)—H(5A)179.1
O(2V)—V(1)—N(1B)—C(1B)77.4 (3)C(7B)—C(6B)—C(5B)—H(5B)179.6
O(2V)—V(1)—N(1B)—C(9B)100.2 (2)C(8A)—C(7A)—C(6A)—H(6A)178.0
O(2V)—C(1P)—C(2P)—C(3P)0 (1)C(8B)—C(7B)—C(6B)—H(6B)179.1
O(2V)—C(1P)—C(2P)—H(2PA)125.9C(9A)—N(1A)—C(1A)—H(1A)177.9
O(2V)—C(1P)—C(2P)—H(2PB)124.5C(9A)—C(4A)—C(3A)—H(3A)179.3
N(1A)—V(1)—O(1A)—C(8A)4.0 (2)C(9A)—C(4A)—C(5A)—H(5A)178.1
N(1A)—V(1)—O(1B)—C(8B)83.2 (2)C(9A)—C(8A)—C(7A)—H(7A)176.9
N(1A)—V(1)—O(2V)—C(1P)160.0 (5)C(9B)—N(1B)—C(1B)—H(1B)179.2
N(1A)—V(1)—N(1B)—C(1B)94.8 (3)C(9B)—C(4B)—C(3B)—H(3B)179.0
N(1A)—V(1)—N(1B)—C(9B)87.6 (2)C(9B)—C(4B)—C(5B)—H(5B)178.6
N(1A)—C(1A)—C(2A)—C(3A)0.9 (7)C(9B)—C(8B)—C(7B)—H(7B)178.7
N(1A)—C(1A)—C(2A)—H(2A)178.5H(1A)—C(1A)—C(2A)—H(2A)2.5
N(1A)—C(9A)—C(4A)—C(3A)1.4 (6)H(1B)—C(1B)—C(2B)—H(2B)1.5
N(1A)—C(9A)—C(4A)—C(5A)177.7 (4)H(1PA)—C(1P)—C(2P)—H(2PA)5.0
N(1A)—C(9A)—C(8A)—C(7A)175.9 (3)H(1PA)—C(1P)—C(2P)—H(2PB)114.6
N(1B)—V(1)—O(1A)—C(8A)78.1 (2)H(1PB)—C(1P)—C(2P)—H(2PA)112.5
N(1B)—V(1)—O(1B)—C(8B)1.5 (2)H(1PB)—C(1P)—C(2P)—H(2PB)2.9
N(1B)—V(1)—O(2V)—C(1P)169.4 (4)H(2A)—C(2A)—C(3A)—H(3A)2.4
N(1B)—V(1)—N(1A)—C(1A)98.0 (4)H(2B)—C(2B)—C(3B)—H(3B)1.3
N(1B)—V(1)—N(1A)—C(9A)82.1 (2)H(5A)—C(5A)—C(6A)—H(6A)2.6
N(1B)—C(1B)—C(2B)—C(3B)0.6 (5)H(5B)—C(5B)—C(6B)—H(6B)0.4
N(1B)—C(1B)—C(2B)—H(2B)179.5H(6A)—C(6A)—C(7A)—H(7A)2.2
N(1B)—C(9B)—C(4B)—C(3B)0.4 (4)H(6B)—C(6B)—C(7B)—H(7B)1.7
N(1B)—C(9B)—C(4B)—C(5B)179.4 (3)H(6B)—C(6B)—C(7B)—H(7B)1.7
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x+2, y+1, z+1; (v) x, y, z.

Experimental details

Crystal data
Chemical formulaC21H19N2O4V
Mr414.33
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.639 (3), 12.751 (3), 9.044 (3)
α, β, γ (°)95.76 (2), 110.97 (2), 108.63 (2)
V3)954.1 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.20 × 0.20 × 0.07
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.896, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
4645, 4391, 2952
Rint0.018
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.176, 1.14
No. of reflections4389
No. of parameters253
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.64, 0.43

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999), SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
V(1)—O(1A)1.924 (3)V(1)—N(1B)2.307 (3)
V(1)—O(1B)1.888 (3)O(1A)—C(8A)1.328 (4)
V(1)—O(1V)1.600 (3)O(1B)—C(8B)1.338 (5)
V(1)—O(2V)1.775 (2)O(2V)—C(1P)1.420 (6)
V(1)—N(1A)2.207 (3)
O(1A)—V(1)—O(1B)153.0 (1)O(1V)—V(1)—N(1B)169.6 (1)
O(1A)—V(1)—O(1V)103.0 (1)O(2V)—V(1)—N(1A)164.8 (1)
O(1A)—V(1)—O(2V)93.7 (1)O(2V)—V(1)—N(1B)86.4 (1)
O(1A)—V(1)—N(1A)76.9 (1)N(1A)—V(1)—N(1B)80.52 (10)
O(1A)—V(1)—N(1B)82.1 (1)V(1)—O(1A)—C(8A)120.8 (2)
O(1B)—V(1)—O(1V)96.2 (1)V(1)—O(1B)—C(8B)123.0 (2)
O(1B)—V(1)—O(2V)100.6 (1)V(1)—O(2V)—C(1P)129.7 (2)
O(1B)—V(1)—N(1A)83.8 (1)V(1)—N(1A)—C(1A)130.5 (3)
O(1B)—V(1)—N(1B)76.2 (1)V(1)—N(1A)—C(9A)111.2 (2)
O(1V)—V(1)—O(2V)102.1 (1)V(1)—N(1B)—C(1B)132.9 (3)
O(1V)—V(1)—N(1A)91.7 (1)V(1)—N(1B)—C(9B)108.5 (2)
V(1)—O(1A)—C(8A)—C(7A)173.7 (3)O(1V)—V(1)—O(1B)—C(8B)174.3 (2)
V(1)—O(1B)—C(8B)—C(7B)178.1 (2)O(1V)—V(1)—O(2V)—C(1P)4.6 (4)
V(1)—O(2V)—C(1P)—C(2P)91.6 (5)O(2V)—C(1P)—C(2P)—C(3P)0 (1)
O(1A)—V(1)—O(2V)—C(1P)108.7 (4)N(1A)—V(1)—O(1B)—C(8B)83.2 (2)
O(1A)—V(1)—N(1B)—C(1B)16.9 (3)N(1B)—V(1)—O(1A)—C(8A)78.1 (2)
O(1B)—V(1)—O(2V)—C(1P)94.2 (4)N(1B)—V(1)—O(2V)—C(1P)169.4 (4)
O(1V)—V(1)—O(1A)—C(8A)92.7 (3)
 

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