Crystal structure of (2-formyl-phenolato-κ(2) O,O')oxido(2-{[(2-oxidoeth-yl)imino]-meth-yl}phenolato-κ(3) O,N,O')vanadium(V).

In the unsymmetrical title vanadyl complex, [V(C9H9NO2)(C7H5O2)O], one of the ligands (2-formyl-phenol) is disordered over two sets of sites, with an occupancy ratio of 0.55 (2):0.45 (2). The metal atom is hexa-coordinated, with a distorted octa-hedral geometry. The vanadyl O atom (which subtends the shortest V-O bond) occupies one of the apical positions and the remaining axial bond (the longest in the polyhedron) is provided by the (disordered) formyl O atoms. The basal plane is defined by the two phenoxide O atoms, the imino-alcoholic O and the imino N atom. The planes of the two benzene rings are almost perpendicular to each other, subtending an inter-planar angle of 84.1 (2)° between the major parts. The crystal structure features weak C-H⋯O and C-H⋯π inter-actions, forming a lateral arrangement of adjacent molecules.

Related literature

For general background to catalysis, see: Forzatti et al. (1987 ▸); Harding et al. (1994 ▸); Xia et al. (2012 ▸); Salavati-Niasari et al. (2004 ▸). For C—H oxidation reactions, see: Grivani et al. (2013 ▸); Maurya et al. (2011 ▸); Talsi et al. (1993 ▸); Zhang et al. (2005 ▸).

Experimental

Crystal data

[V(C9H9NO2)(C7H5O2)O]

M = 351.22

Monoclinic,

a = 6.6915 (2) Å

b = 7.6542 (4) Å

c = 29.1847 (9) Å

β = 95.126 (3)°

V = 1488.81 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 293 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.846, T max = 0.880

18824 measured reflections

3249 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.22

3249 reflections

290 parameters

143 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: SHELXL2014/7.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015006477/bg2547sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006477/bg2547Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015006477/bg2547fig1.tif

Mol­ecular structure of the title compound with atom labelling. Displacement ellipsoids are drawn at 30% probability level. (The minor component of the disordered 2-formyl­phenol moiety is not shown).

CCDC reference: 1057002

Additional supporting information: crystallographic information; 3D view; checkCIF report

[V(C9H9NO2)(C7H5O2)O]	F(000) = 720
Mr = 351.22	Dx = 1.567 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6915 (2) Å	Cell parameters from 7573 reflections
b = 7.6542 (4) Å	θ = 2.8–29.9°
c = 29.1847 (9) Å	µ = 0.69 mm−1
β = 95.126 (3)°	T = 293 K
V = 1488.81 (10) Å3	Blocks, black
Z = 4	0.25 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
ω and φ scan	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.846, Tmax = 0.880	k = −9→9
18824 measured reflections	l = −37→37
3249 independent reflections

Refinement on F2	143 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0298P)2 + 1.478P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max = 0.001
3249 reflections	Δρmax = 0.29 e Å−3
290 parameters	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
V1	0.26635 (5)	0.25635 (6)	0.12647 (2)	0.02941 (13)
N1	0.5270 (3)	0.2221 (3)	0.17101 (7)	0.0309 (4)
O1	0.1761 (2)	0.3678 (2)	0.17886 (5)	0.0335 (4)
O2	0.4526 (3)	0.2057 (3)	0.08602 (6)	0.0441 (5)
O5	0.1870 (3)	0.0660 (3)	0.13678 (7)	0.0430 (4)
C1	0.1947 (3)	0.3159 (3)	0.22234 (8)	0.0283 (5)
C2	0.0450 (4)	0.3559 (3)	0.25122 (9)	0.0353 (5)
H2	−0.0677	0.4184	0.2398	0.042*
C3	0.0638 (4)	0.3033 (4)	0.29651 (9)	0.0430 (6)
H3	−0.0391	0.3274	0.3150	0.052*
C4	0.2328 (5)	0.2150 (4)	0.31514 (9)	0.0450 (7)
H4	0.2430	0.1793	0.3457	0.054*
C5	0.3843 (4)	0.1810 (4)	0.28796 (9)	0.0392 (6)
H5	0.5002	0.1259	0.3006	0.047*
C6	0.3684 (3)	0.2278 (3)	0.24135 (8)	0.0315 (5)
C7	0.5346 (3)	0.1987 (3)	0.21439 (9)	0.0334 (5)
H7	0.6550	0.1606	0.2295	0.040*
C8	0.7059 (4)	0.1994 (4)	0.14621 (10)	0.0395 (6)
H8A	0.8031	0.1246	0.1633	0.047*
H8B	0.7682	0.3111	0.1409	0.047*
C9	0.6286 (4)	0.1157 (4)	0.10163 (10)	0.0438 (6)
H9A	0.7273	0.1248	0.0793	0.053*
H9B	0.5998	−0.0069	0.1063	0.053*
O3	0.0652 (12)	0.3279 (8)	0.0824 (4)	0.0280 (19)	0.55 (2)
O4	0.3721 (14)	0.5368 (8)	0.1196 (5)	0.035 (2)	0.55 (2)
C10	0.2794 (14)	0.6543 (7)	0.0990 (4)	0.0368 (19)	0.55 (2)
H10	0.3396	0.7639	0.1000	0.044*	0.55 (2)
C11	0.0863 (13)	0.6404 (7)	0.0732 (3)	0.0310 (16)	0.55 (2)
C12	0.0013 (15)	0.7914 (8)	0.0525 (3)	0.043 (2)	0.55 (2)
H12	0.0660	0.8983	0.0572	0.052*	0.55 (2)
C13	−0.1765 (14)	0.7829 (11)	0.0252 (3)	0.044 (2)	0.55 (2)
H13	−0.2320	0.8833	0.0114	0.053*	0.55 (2)
C14	−0.2714 (11)	0.6253 (12)	0.0186 (3)	0.0386 (18)	0.55 (2)
H14	−0.3922	0.6200	0.0002	0.046*	0.55 (2)
C15	−0.1924 (9)	0.4741 (11)	0.0386 (3)	0.0338 (17)	0.55 (2)
H15	−0.2611	0.3690	0.0340	0.041*	0.55 (2)
C16	−0.0087 (11)	0.4785 (8)	0.0657 (4)	0.0262 (16)	0.55 (2)
O3'	0.0547 (14)	0.3519 (9)	0.0891 (5)	0.028 (2)	0.45 (2)
O4'	0.4058 (16)	0.5227 (10)	0.1170 (6)	0.039 (3)	0.45 (2)
C10'	0.3244 (16)	0.6488 (8)	0.0978 (5)	0.041 (3)	0.45 (2)
H10'	0.3946	0.7538	0.1001	0.050*	0.45 (2)
C11'	0.1309 (15)	0.6516 (8)	0.0720 (5)	0.037 (2)	0.45 (2)
C12'	0.0638 (18)	0.8090 (8)	0.0514 (4)	0.043 (2)	0.45 (2)
H12'	0.1444	0.9080	0.0547	0.052*	0.45 (2)
C13'	−0.1199 (18)	0.8183 (11)	0.0266 (4)	0.045 (2)	0.45 (2)
H13'	−0.1619	0.9218	0.0121	0.054*	0.45 (2)
C14'	−0.2409 (14)	0.6738 (14)	0.0234 (4)	0.043 (2)	0.45 (2)
H14'	−0.3661	0.6809	0.0069	0.052*	0.45 (2)
C15'	−0.1817 (13)	0.5178 (13)	0.0441 (4)	0.039 (2)	0.45 (2)
H15'	−0.2659	0.4211	0.0410	0.047*	0.45 (2)
C16'	0.0050 (13)	0.5050 (10)	0.0697 (5)	0.031 (2)	0.45 (2)

	U11	U22	U33	U12	U13	U23
V1	0.0230 (2)	0.0370 (2)	0.0279 (2)	−0.00340 (17)	0.00052 (14)	0.00299 (17)
N1	0.0210 (9)	0.0339 (11)	0.0381 (11)	0.0003 (8)	0.0031 (8)	0.0045 (9)
O1	0.0282 (8)	0.0432 (10)	0.0289 (8)	0.0098 (7)	0.0016 (6)	0.0045 (7)
O2	0.0359 (9)	0.0629 (13)	0.0347 (9)	0.0014 (9)	0.0096 (8)	−0.0020 (9)
O5	0.0384 (10)	0.0422 (11)	0.0479 (11)	−0.0069 (8)	0.0020 (8)	0.0045 (9)
C1	0.0277 (11)	0.0292 (11)	0.0275 (11)	−0.0026 (9)	−0.0002 (9)	−0.0030 (9)
C2	0.0324 (13)	0.0342 (13)	0.0398 (13)	0.0035 (10)	0.0056 (10)	−0.0041 (11)
C3	0.0520 (16)	0.0416 (15)	0.0376 (14)	−0.0031 (13)	0.0153 (12)	−0.0097 (12)
C4	0.0621 (18)	0.0452 (16)	0.0273 (12)	−0.0051 (14)	0.0025 (12)	−0.0001 (11)
C5	0.0418 (14)	0.0405 (14)	0.0336 (13)	0.0004 (12)	−0.0058 (11)	0.0037 (11)
C6	0.0299 (11)	0.0329 (13)	0.0306 (12)	−0.0031 (10)	−0.0024 (9)	0.0016 (10)
C7	0.0226 (11)	0.0355 (13)	0.0407 (13)	0.0017 (9)	−0.0057 (9)	0.0059 (11)
C8	0.0230 (11)	0.0460 (15)	0.0508 (16)	0.0018 (11)	0.0102 (10)	0.0048 (12)
C9	0.0386 (14)	0.0441 (15)	0.0513 (16)	0.0002 (12)	0.0186 (12)	−0.0007 (13)
O3	0.030 (3)	0.036 (2)	0.017 (3)	−0.0034 (18)	−0.002 (2)	−0.002 (2)
O4	0.026 (3)	0.040 (3)	0.036 (3)	−0.007 (2)	−0.003 (3)	−0.002 (2)
C10	0.034 (3)	0.038 (3)	0.037 (3)	−0.0057 (17)	−0.005 (3)	−0.004 (2)
C11	0.031 (3)	0.037 (2)	0.024 (3)	−0.0048 (15)	0.000 (2)	−0.0031 (16)
C12	0.042 (4)	0.036 (3)	0.048 (3)	−0.007 (2)	−0.013 (3)	0.000 (2)
C13	0.041 (4)	0.038 (3)	0.048 (3)	−0.004 (2)	−0.014 (3)	0.000 (2)
C14	0.040 (3)	0.040 (3)	0.033 (3)	−0.005 (2)	−0.012 (2)	0.000 (2)
C15	0.032 (2)	0.039 (3)	0.028 (3)	−0.0076 (19)	−0.0067 (19)	0.001 (3)
C16	0.028 (2)	0.035 (2)	0.015 (3)	−0.0042 (15)	0.0015 (18)	−0.0029 (19)
O3'	0.026 (3)	0.035 (3)	0.022 (4)	−0.005 (2)	0.001 (2)	−0.002 (3)
O4'	0.029 (4)	0.048 (4)	0.039 (4)	−0.009 (3)	0.005 (3)	0.003 (3)
C10'	0.037 (4)	0.045 (4)	0.041 (4)	−0.011 (2)	−0.001 (3)	0.000 (3)
C11'	0.038 (3)	0.039 (3)	0.034 (4)	−0.008 (2)	0.003 (3)	−0.002 (2)
C12'	0.048 (4)	0.038 (3)	0.042 (4)	−0.009 (2)	−0.005 (4)	−0.001 (3)
C13'	0.049 (4)	0.039 (3)	0.046 (4)	−0.008 (3)	−0.007 (3)	−0.004 (3)
C14'	0.040 (4)	0.039 (3)	0.048 (5)	−0.004 (3)	−0.013 (3)	−0.001 (3)
C15'	0.040 (3)	0.038 (3)	0.037 (4)	−0.003 (2)	−0.008 (3)	−0.004 (3)
C16'	0.034 (3)	0.037 (3)	0.020 (4)	−0.0031 (19)	0.001 (2)	−0.001 (3)

V1—O5	1.5886 (19)	O3—C16	1.330 (4)
V1—O3	1.859 (3)	O4—C10	1.220 (4)
V1—O2	1.8333 (18)	C10—C11	1.439 (5)
V1—O1	1.8957 (17)	C10—H10	0.9300
V1—O3'	1.859 (3)	C11—C12	1.402 (4)
V1—N1	2.0966 (19)	C11—C16	1.401 (5)
V1—O4'	2.269 (4)	C12—C13	1.372 (6)
V1—O4	2.275 (3)	C12—H12	0.9300
N1—C7	1.275 (3)	C13—C14	1.369 (7)
N1—C8	1.464 (3)	C13—H13	0.9300
O1—C1	1.325 (3)	C14—C15	1.379 (5)
O2—C9	1.404 (3)	C14—H14	0.9300
C1—C2	1.400 (3)	C15—C16	1.401 (4)
C1—C6	1.413 (3)	C15—H15	0.9300
C2—C3	1.377 (4)	O3'—C16'	1.330 (4)
C2—H2	0.9300	O4'—C10'	1.220 (4)
C3—C4	1.386 (4)	C10'—C11'	1.439 (5)
C3—H3	0.9300	C10'—H10'	0.9300
C4—C5	1.367 (4)	C11'—C12'	1.402 (4)
C4—H4	0.9300	C11'—C16'	1.401 (5)
C5—C6	1.401 (3)	C12'—C13'	1.372 (6)
C5—H5	0.9300	C12'—H12'	0.9300
C6—C7	1.436 (3)	C13'—C14'	1.369 (7)
C7—H7	0.9300	C13'—H13'	0.9300
C8—C9	1.500 (4)	C14'—C15'	1.380 (5)
C8—H8A	0.9700	C14'—H14'	0.9300
C8—H8B	0.9700	C15'—C16'	1.402 (4)
C9—H9A	0.9700	C15'—H15'	0.9300
C9—H9B	0.9700
O5—V1—O3	99.65 (14)	C9—C8—H8B	110.9
O5—V1—O2	100.72 (10)	H8A—C8—H8B	108.9
O3—V1—O2	96.2 (5)	O2—C9—C8	106.6 (2)
O5—V1—O1	97.12 (9)	O2—C9—H9A	110.4
O3—V1—O1	99.3 (5)	C8—C9—H9A	110.4
O2—V1—O1	153.94 (8)	O2—C9—H9B	110.4
O5—V1—O3'	102.82 (18)	C8—C9—H9B	110.4
O2—V1—O3'	103.4 (6)	H9A—C9—H9B	108.6
O1—V1—O3'	90.9 (6)	C16—O3—V1	137.1 (4)
O5—V1—N1	92.39 (9)	C10—O4—V1	126.2 (3)
O3—V1—N1	167.5 (2)	O4—C10—C11	126.6 (3)
O2—V1—N1	78.28 (8)	O4—C10—H10	116.7
O1—V1—N1	82.15 (7)	C11—C10—H10	116.7
O3'—V1—N1	164.0 (2)	C12—C11—C16	120.1 (4)
O5—V1—O4'	174.29 (18)	C12—C11—C10	118.4 (4)
O2—V1—O4'	78.5 (5)	C16—C11—C10	121.4 (3)
O1—V1—O4'	81.8 (5)	C13—C12—C11	120.5 (4)
O3'—V1—O4'	82.83 (15)	C13—C12—H12	119.7
N1—V1—O4'	81.91 (16)	C11—C12—H12	119.7
O5—V1—O4	173.8 (4)	C12—C13—C14	119.4 (4)
O3—V1—O4	82.66 (13)	C12—C13—H13	120.3
O2—V1—O4	84.7 (4)	C14—C13—H13	120.3
O1—V1—O4	76.8 (4)	C13—C14—C15	121.6 (4)
N1—V1—O4	85.69 (13)	C13—C14—H14	119.2
C7—N1—C8	120.8 (2)	C15—C14—H14	119.2
C7—N1—V1	126.16 (16)	C14—C15—C16	120.1 (4)
C8—N1—V1	112.34 (16)	C14—C15—H15	119.9
C1—O1—V1	128.93 (15)	C16—C15—H15	119.9
C9—O2—V1	119.57 (16)	O3—C16—C15	117.7 (4)
O1—C1—C2	120.0 (2)	O3—C16—C11	124.1 (3)
O1—C1—C6	121.5 (2)	C15—C16—C11	118.2 (3)
C2—C1—C6	118.4 (2)	C16'—O3'—V1	138.1 (2)
C3—C2—C1	120.4 (2)	C10'—O4'—V1	126.5 (3)
C3—C2—H2	119.8	O4'—C10'—C11'	126.6 (3)
C1—C2—H2	119.8	O4'—C10'—H10'	116.7
C2—C3—C4	121.3 (3)	C11'—C10'—H10'	116.7
C2—C3—H3	119.3	C12'—C11'—C16'	120.0 (4)
C4—C3—H3	119.3	C12'—C11'—C10'	118.4 (4)
C5—C4—C3	119.1 (2)	C16'—C11'—C10'	121.4 (3)
C5—C4—H4	120.4	C13'—C12'—C11'	120.5 (4)
C3—C4—H4	120.4	C13'—C12'—H12'	119.7
C4—C5—C6	121.2 (2)	C11'—C12'—H12'	119.7
C4—C5—H5	119.4	C12'—C13'—C14'	119.4 (4)
C6—C5—H5	119.4	C12'—C13'—H13'	120.3
C5—C6—C1	119.5 (2)	C14'—C13'—H13'	120.3
C5—C6—C7	119.8 (2)	C13'—C14'—C15'	121.6 (4)
C1—C6—C7	120.6 (2)	C13'—C14'—H14'	119.2
N1—C7—C6	123.9 (2)	C15'—C14'—H14'	119.2
N1—C7—H7	118.0	C14'—C15'—C16'	120.1 (4)
C6—C7—H7	118.0	C14'—C15'—H15'	119.9
N1—C8—C9	104.2 (2)	C16'—C15'—H15'	119.9
N1—C8—H8A	110.9	O3'—C16'—C15'	117.7 (4)
C9—C8—H8A	110.9	O3'—C16'—C11'	124.0 (3)
N1—C8—H8B	110.9	C15'—C16'—C11'	118.2 (3)
O5—V1—O1—C1	46.7 (2)	O4—V1—O3—C16	−16.3 (14)
O3—V1—O1—C1	147.7 (2)	V1—O4—C10—C11	−2.3 (18)
O2—V1—O1—C1	−86.3 (3)	O4—C10—C11—C12	178.8 (12)
O3'—V1—O1—C1	149.7 (3)	O4—C10—C11—C16	−6.3 (16)
N1—V1—O1—C1	−44.75 (19)	C16—C11—C12—C13	1.0 (14)
O4'—V1—O1—C1	−127.6 (2)	C10—C11—C12—C13	176.0 (8)
O4—V1—O1—C1	−132.1 (2)	C11—C12—C13—C14	0.4 (12)
O5—V1—O2—C9	−68.2 (2)	C12—C13—C14—C15	−0.2 (12)
O3—V1—O2—C9	−169.3 (2)	C13—C14—C15—C16	−1.3 (13)
O1—V1—O2—C9	64.2 (3)	V1—O3—C16—C15	−166.8 (12)
O3'—V1—O2—C9	−174.3 (3)	V1—O3—C16—C11	14 (2)
N1—V1—O2—C9	22.07 (19)	C14—C15—C16—O3	−177.1 (11)
O4'—V1—O2—C9	106.1 (3)	C14—C15—C16—C11	2.5 (13)
O4—V1—O2—C9	108.7 (2)	C12—C11—C16—O3	177.2 (12)
V1—O1—C1—C2	−147.23 (18)	C10—C11—C16—O3	2.3 (15)
V1—O1—C1—C6	36.1 (3)	C12—C11—C16—C15	−2.4 (13)
O1—C1—C2—C3	−179.7 (2)	C10—C11—C16—C15	−177.2 (9)
C6—C1—C2—C3	−2.9 (4)	O5—V1—O3'—C16'	174.4 (17)
C1—C2—C3—C4	2.1 (4)	O2—V1—O3'—C16'	−81.1 (18)
C2—C3—C4—C5	0.6 (4)	O1—V1—O3'—C16'	76.9 (18)
C3—C4—C5—C6	−2.5 (4)	N1—V1—O3'—C16'	13 (4)
C4—C5—C6—C1	1.7 (4)	O4'—V1—O3'—C16'	−4.7 (17)
C4—C5—C6—C7	176.7 (3)	V1—O4'—C10'—C11'	−8 (2)
O1—C1—C6—C5	177.7 (2)	O4'—C10'—C11'—C12'	−178.7 (16)
C2—C1—C6—C5	1.0 (4)	O4'—C10'—C11'—C16'	6 (2)
O1—C1—C6—C7	2.8 (4)	C16'—C11'—C12'—C13'	−4.1 (17)
C2—C1—C6—C7	−173.9 (2)	C10'—C11'—C12'—C13'	−179.8 (10)
C8—N1—C7—C6	176.5 (2)	C11'—C12'—C13'—C14'	2.4 (15)
V1—N1—C7—C6	−13.5 (4)	C12'—C13'—C14'—C15'	−0.8 (14)
C5—C6—C7—N1	173.2 (2)	C13'—C14'—C15'—C16'	1.0 (16)
C1—C6—C7—N1	−11.9 (4)	V1—O3'—C16'—C15'	−178.2 (15)
C7—N1—C8—C9	141.9 (2)	V1—O3'—C16'—C11'	4 (2)
V1—N1—C8—C9	−29.4 (2)	C14'—C15'—C16'—O3'	179.8 (13)
V1—O2—C9—C8	−45.1 (3)	C14'—C15'—C16'—C11'	−2.6 (17)
N1—C8—C9—O2	44.1 (3)	C12'—C11'—C16'—O3'	−178.5 (15)
O5—V1—O3—C16	157.8 (14)	C10'—C11'—C16'—O3'	−2.9 (19)
O2—V1—O3—C16	−100.1 (14)	C12'—C11'—C16'—C15'	4.1 (17)
O1—V1—O3—C16	58.9 (15)	C10'—C11'—C16'—C15'	179.7 (12)
N1—V1—O3—C16	−37 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5i	0.93	2.56	3.352 (4)	143
C5—H5···O4ii	0.93	2.50	3.220 (13)	134
C2—H2···Cgi	0.93	2.84	3.615 (3)	141

Table 1

Selected bond lengths ()

V1O5	1.5886(19)
V1O3	1.859(3)
V1O2	1.8333(18)
V1O1	1.8957(17)
V1O3	1.859(3)
V1N1	2.0966(19)
V1O4	2.269(4)
V1O4	2.275(3)

Table 2

Hydrogen-bond geometry (, )

Cg is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
C3H3O5i	0.93	2.56	3.352(4)	143
C5H5O4ii	0.93	2.50	3.220(13)	134
C2H2Cg i	0.93	2.84	3.615(3)	141

Symmetry codes: (i) ; (ii) .