A monoclinic polymorph of di-μ-oxido-bis­({2-[2-(methyl­amino)ethyl­imino­methyl]phenolato-κ3N,N′,O}oxidovanadium(V))

Romanowski, G.; Wera, M.; Sikorski, A.

doi:10.1107/S160053680803328X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1548-m1549

doi:10.1107/S160053680803328X

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A monoclinic polymorph of di-μ-oxido-bis({2-[2-(methylamino)ethyliminomethyl]phenolato-κ³N,N′,O}oxidovanadium(V))

Grzegorz Romanowski,^a ^* Michał Wera ^a and Artur Sikorski ^a

^aUniversity of Gdańsk, Faculty of Chemistry, Sobieskiego 18/19, 80-952 Gdańsk, Poland
^*Correspondence e-mail: greg@chem.univ.gda.pl

(Received 9 October 2008; accepted 13 October 2008; online 13 November 2008)

A new monoclinic polymorph of the title compound, [V₂(C₁₀H₁₃N₂O)₂O₄], which is a centrosymmetric dimer, crystallizes in space group P2₁/c, whereas the previously known polymorph crystallizes in the orthorhombic space group Pbca [Mokry & Carrano (1993 ). Inorg. Chem. 32, 6119–6121]. Each V^V atom is six-coordinated by one oxide group, two N atoms and one O atom from the Schiff base ligand, and by two additional bridging O atoms. The two methylene groups are each disordered over two sites, with occupancy factors of 0.776 (14) and 0.224 (14). In the crystal structure, there are C—H⋯O hydrogen bonds and C—H⋯π interactions between the dimers.

Related literature

For general background, see: Butler & Walker (1993 ); Carter-Franklin et al. (2003 ); Eady (2003 ); Evangelou (2002 ); Mendz (1991 ); Rehder et al. (2003 ); Sakurai (2002 ). For related structures, see: Mokry & Carrano (1993); Rao et al. (1981 ); Romanowski et al. (2008 ); Root et al. (1993 ). For the synthesis, see: Kwiatkowski et al. (2003 ).

Experimental

Crystal data

[V₂(C₁₀H₁₃N₂O)₂O₄]
M_r = 520.33
Monoclinic, P 2₁ /c
a = 6.6801 (2) Å
b = 11.9955 (6) Å
c = 13.8643 (7) Å
β = 92.156 (4)°
V = 1110.18 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 295 (2) K
0.6 × 0.1 × 0.1 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.532, T_max = 0.915
6336 measured reflections
1960 independent reflections
1288 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 0.90
1960 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

O7—V14	1.926 (2)
N9—V14	2.158 (3)
N12—V14	2.146 (3)
V14—O16	1.612 (2)
V14—O15	1.674 (2)
V14—O15ⁱ	2.316 (2)
Symmetry code: (i) -x, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O16ⁱⁱ	0.93	2.60	3.520 (4)	170
C11B—H11C⋯Cg1ⁱⁱⁱⁱⁱⁱ	0.97	2.82	3.47 (2)	124
Symmetry codes: (ii) x+1, y, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803328X/hy2159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803328X/hy2159Isup2.hkl

checkCIF report

Comment top

In the past few decades, the interest in the coordination chemistry and biochemistry of vanadium compounds has increased due to their influence on biological systems, viz. in diabetes mellitus (Sakurai, 2002) and cancer treatment (Evangelou, 2002). Moreover, vanadium activity has been discovered in the inhibitory and promotory processes like nitrogenases (Eady, 2003), haloperoxidases (Butler & Walker, 1993; Carter-Franklin et al., 2003; Rehder et al., 2003), mutases and isomerases (Mendz, 1991).

The structure of the title compound was first reported in orthorhombic space group Pbca (Mokry & Carrano, 1993). Here we report the synthesis and structure of a new polymorph of the compound in space group P2₁/c. We have described earlier the spectroscopic properties (IR, UV-Vis, ¹H and ⁵¹V NMR) of this compound (Kwiatkowski et al., 2003). The half of the molecule, constituting the asymmetric unit of the structure, is related to the other half by a center of symmetry. Each V^V atom is six-coordinated by two strongly (O15, O16) and one weakly (O15ⁱ) associated oxide groups and by the tridentate Schiff base ligand, viz. a phenolate O atom (O7), a secondary amine N atom (N12), both occupying the axial positions, and an imine N atom (N9) (Fig. 1). The geometry about the V atom is distorted octahedral. The V14 ═O16 bond length of 1.612 (2) Å (Table 1) compares well with the distances between V and the doubly bonded O atoms (Romanowski et al., 2008; Root et al., 1993). The V14, O15, V14ⁱ, O15ⁱ atoms are situated at vertices of a parallelogram with the acute O15—V14—O15ⁱ angle of 78.64 (8)° [symmetry code: (i) -x, -y+2, -z]. The five-membered ring comprising the ethylenediamine moiety exhibits twofold disorder. The C10 and C11 atoms are disordered over two sites, with occupancy factors of 0.776 (14) and 0.224 (14) for C10A/C11A and C10B/C11B, respectively. The five-membered chelate ring defined by V14, N9, C10A, C11A, N12 adopts an envelope conformation on C10A, with P = 244.0 (3)° and τ₍_M₎ = 54.9 (4)° for reference bond V14—N9 (Rao et al., 1981) and the ring formed by V14, N9, C10B, C11B, N12 takes the envelope conformation on C11B, with P = 81.8 (7)° and τ₍_M₎ = 62.3 (9)° for reference bond V14—N9 (Fig. 1).

In the crystal structure, the dimers are linked through C—H···O hydrogen bonds (Table 1), forming columns along the a-axis. There are C—H···π interactions (Fig. 2), involving minor disordered C11B atom [C11B···Cg1ⁱⁱⁱ = 3.47 (2), H11C···Cg1ⁱⁱⁱ = 2.82 Å; Cg1 = centroid of the ring C1–C6; symmetry code: (iii) x, 3/2-y, -1/2+z].

Related literature top

For general background, see: Butler & Walker (1993); Carter-Franklin et al. (2003); Eady (2003); Evangelou (2002); Mendz (1991); Rehder et al. (2003); Sakurai (2002). For related structures, see: Mokry & Carrano (1993); Rao et al. (1981); Romanowski et al. (2008); Root et al. (1993). For the synthesis, see: Kwiatkowski et al. (2003).

Experimental top

The title compound was obtained in a template/complexation reaction, which was described earlier (Kwiatkowski et al., 2003). A solution of N-methylethylenediamine (1 mmol) in absolute EtOH (10 ml) was added under stirring to a freshly filtered solution of vanadium(V) oxytriethoxide (1 mmol) in absolute EtOH (50 ml), producing a yellow suspension of the intermediate. Salicylaldehyde (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.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 25% probability level. [Symmetry code: (i) -x, -y+2, -z.]
	Fig. 2. The arrangement of the molecules viewed approximately along the a-axis. The C—H···O hydrogen bonds are represented by dashed lines and the C—H···π interactions are represented by dotted lines. [Symmetry codes: (ii) 1+x, y, z; (iii) x, 3/2-y, -1/2+z.]

di-µ-oxido-bis({2-[2-(methylamino)ethyliminomethyl]phenolato- κ³N,N',O}oxidovanadium(V)) top

Crystal data top

[V₂(C₁₀H₁₃N₂O)₂O₄]	F(000) = 536
M_r = 520.33	D_x = 1.557 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1960 reflections
a = 6.6801 (2) Å	θ = 3.1–25.1°
b = 11.9955 (6) Å	µ = 0.89 mm⁻¹
c = 13.8643 (7) Å	T = 295 K
β = 92.156 (4)°	Needle, yellow
V = 1110.18 (9) Å³	0.6 × 0.1 × 0.1 mm
Z = 2

Data collection top

Oxford Diffraction Ruby CCD diffractometer	1960 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.1°, θ_min = 3.1°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→14
T_min = 0.532, T_max = 0.915	l = −13→16
6336 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.064P)²] where P = (F_o² + 2F_c²)/3
1960 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[V₂(C₁₀H₁₃N₂O)₂O₄]	V = 1110.18 (9) Å³
M_r = 520.33	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.6801 (2) Å	µ = 0.89 mm⁻¹
b = 11.9955 (6) Å	T = 295 K
c = 13.8643 (7) Å	0.6 × 0.1 × 0.1 mm
β = 92.156 (4)°

Data collection top

Oxford Diffraction Ruby CCD diffractometer	1960 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1288 reflections with I > 2σ(I)
T_min = 0.532, T_max = 0.915	R_int = 0.050
6336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 0.90	Δρ_max = 0.36 e Å⁻³
1960 reflections	Δρ_min = −0.39 e Å⁻³
155 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.2360 (4)	0.9625 (3)	0.2273 (2)	0.0439 (8)
C2	0.4291 (4)	0.9220 (3)	0.2071 (2)	0.0463 (9)
C3	0.5887 (5)	0.9466 (4)	0.2713 (3)	0.0609 (10)
H3A	0.7156	0.9199	0.2583	0.073*
C4	0.5646 (6)	1.0085 (4)	0.3528 (3)	0.0739 (12)
H4A	0.6735	1.0239	0.3945	0.089*
C5	0.3749 (6)	1.0482 (4)	0.3724 (3)	0.0696 (11)
H5A	0.3562	1.0900	0.4278	0.084*
C6	0.2169 (5)	1.0261 (3)	0.3110 (2)	0.0553 (9)
H6A	0.0916	1.0542	0.3250	0.066*
O7	0.0760 (3)	0.9451 (2)	0.16978 (15)	0.0495 (6)
C8	0.4690 (5)	0.8585 (3)	0.1220 (3)	0.0505 (9)
H8A	0.5981	0.8309	0.1163	0.061*
N9	0.3417 (4)	0.8368 (3)	0.0538 (2)	0.0514 (8)
C10A	0.3951 (9)	0.7645 (7)	−0.0286 (4)	0.0583 (19)	0.776 (14)
H10A	0.5393	0.7566	−0.0312	0.070*	0.776 (14)
H10B	0.3361	0.6911	−0.0226	0.070*	0.776 (14)
C10B	0.442 (3)	0.820 (2)	−0.0377 (13)	0.042 (6)*	0.224 (14)
H10C	0.5616	0.7741	−0.0293	0.050*	0.224 (14)
H10D	0.4755	0.8895	−0.0683	0.050*	0.224 (14)
C11A	0.3133 (8)	0.8217 (7)	−0.1157 (4)	0.058 (2)	0.776 (14)
H11A	0.3336	0.7765	−0.1726	0.070*	0.776 (14)
H11B	0.3797	0.8928	−0.1239	0.070*	0.776 (14)
C11B	0.272 (2)	0.758 (2)	−0.0932 (14)	0.044 (6)*	0.224 (14)
H11C	0.3148	0.7358	−0.1566	0.053*	0.224 (14)
H11D	0.2347	0.6911	−0.0584	0.053*	0.224 (14)
N12	0.0951 (4)	0.8389 (3)	−0.1021 (2)	0.0504 (7)
H12A	0.0674	0.9027	−0.1355	0.060*
C13	−0.0425 (6)	0.7569 (4)	−0.1475 (3)	0.0758 (12)
H13A	−0.0093	0.7463	−0.2136	0.114*
H13B	−0.1777	0.7836	−0.1448	0.114*
H13C	−0.0305	0.6872	−0.1137	0.114*
V14	0.02849 (7)	0.88119 (5)	0.04358 (4)	0.0417 (2)
O15	−0.1739 (3)	0.95553 (19)	0.00898 (15)	0.0437 (6)
O16	−0.0525 (3)	0.7584 (2)	0.06852 (19)	0.0629 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0506 (18)	0.043 (2)	0.0391 (19)	0.0011 (16)	0.0086 (15)	0.0132 (17)
C2	0.0465 (18)	0.046 (2)	0.047 (2)	0.0026 (16)	0.0079 (16)	0.0110 (17)
C3	0.0506 (19)	0.066 (3)	0.066 (3)	0.0006 (19)	−0.0012 (18)	0.007 (2)
C4	0.061 (2)	0.087 (3)	0.073 (3)	−0.002 (2)	−0.015 (2)	−0.003 (3)
C5	0.084 (3)	0.069 (3)	0.055 (2)	−0.004 (2)	−0.003 (2)	−0.008 (2)
C6	0.063 (2)	0.052 (2)	0.051 (2)	0.0049 (19)	0.0067 (17)	0.005 (2)
O7	0.0427 (11)	0.0664 (17)	0.0397 (13)	0.0116 (12)	0.0066 (10)	0.0001 (12)
C8	0.0410 (17)	0.056 (2)	0.056 (2)	0.0101 (16)	0.0118 (17)	0.0117 (19)
N9	0.0452 (14)	0.065 (2)	0.0452 (17)	0.0181 (14)	0.0153 (14)	0.0048 (16)
C10A	0.050 (3)	0.055 (4)	0.071 (4)	0.015 (3)	0.024 (3)	−0.004 (3)
C11A	0.068 (3)	0.058 (5)	0.050 (3)	0.014 (3)	0.027 (2)	−0.001 (3)
N12	0.0481 (14)	0.0490 (18)	0.0544 (18)	0.0095 (14)	0.0058 (13)	−0.0125 (15)
C13	0.094 (3)	0.063 (3)	0.070 (3)	−0.013 (2)	−0.005 (2)	−0.016 (2)
V14	0.0397 (3)	0.0394 (4)	0.0468 (4)	0.0031 (3)	0.0116 (2)	0.0003 (3)
O15	0.0386 (11)	0.0426 (14)	0.0505 (13)	0.0024 (10)	0.0085 (9)	−0.0031 (11)
O16	0.0645 (14)	0.0455 (15)	0.0805 (19)	0.0012 (12)	0.0262 (13)	0.0087 (14)

Geometric parameters (Å, º) top

C1—O7	1.326 (4)	C10B—C11B	1.54 (3)
C1—C6	1.398 (5)	C10B—H10C	0.9700
C1—C2	1.417 (4)	C10B—H10D	0.9700
C2—C3	1.395 (5)	C11A—N12	1.491 (5)
C2—C8	1.437 (5)	C11A—H11A	0.9700
C3—C4	1.367 (5)	C11A—H11B	0.9700
C3—H3A	0.9300	C11B—N12	1.535 (17)
C4—C5	1.390 (5)	C11B—H11C	0.9700
C4—H4A	0.9300	C11B—H11D	0.9700
C5—C6	1.357 (5)	N12—C13	1.471 (4)
C5—H5A	0.9300	N12—V14	2.146 (3)
C6—H6A	0.9300	N12—H12A	0.9100
O7—V14	1.926 (2)	C13—H13A	0.9600
C8—N9	1.275 (4)	C13—H13B	0.9600
C8—H8A	0.9300	C13—H13C	0.9600
N9—C10B	1.472 (18)	V14—O16	1.612 (2)
N9—C10A	1.489 (6)	V14—O15	1.674 (2)
N9—V14	2.158 (3)	V14—O15ⁱ	2.316 (2)
C10A—C11A	1.476 (9)	V14—V14ⁱ	3.1136 (11)
C10A—H10A	0.9700	O15—V14ⁱ	2.316 (2)
C10A—H10B	0.9700

O7—C1—C6	119.2 (3)	H11A—C11A—H11B	108.5
O7—C1—C2	123.1 (3)	N12—C11B—C10B	106.6 (16)
C6—C1—C2	117.6 (3)	N12—C11B—H11C	110.4
C3—C2—C1	118.8 (3)	C10B—C11B—H11C	110.4
C3—C2—C8	118.4 (3)	N12—C11B—H11D	110.4
C1—C2—C8	122.8 (3)	C10B—C11B—H11D	110.4
C4—C3—C2	122.1 (3)	H11C—C11B—H11D	108.6
C4—C3—H3A	118.9	C13—N12—C11A	116.9 (4)
C2—C3—H3A	118.9	C13—N12—C11B	94.5 (8)
C3—C4—C5	118.9 (4)	C13—N12—V14	114.3 (2)
C3—C4—H4A	120.5	C11A—N12—V14	112.9 (2)
C5—C4—H4A	120.5	C11B—N12—V14	105.1 (7)
C6—C5—C4	120.3 (4)	C13—N12—H12A	103.5
C6—C5—H5A	119.9	C11A—N12—H12A	103.5
C4—C5—H5A	119.9	C11B—N12—H12A	135.8
C5—C6—C1	122.3 (3)	V14—N12—H12A	103.5
C5—C6—H6A	118.9	N12—C13—H13A	109.5
C1—C6—H6A	118.9	N12—C13—H13B	109.5
C1—O7—V14	135.30 (19)	H13A—C13—H13B	109.5
N9—C8—C2	125.3 (3)	N12—C13—H13C	109.5
N9—C8—H8A	117.4	H13A—C13—H13C	109.5
C2—C8—H8A	117.4	H13B—C13—H13C	109.5
C8—N9—C10B	110.8 (7)	O16—V14—O15	105.93 (11)
C8—N9—C10A	121.1 (3)	O16—V14—O7	102.36 (12)
C8—N9—V14	128.1 (2)	O15—V14—O7	98.73 (9)
C10B—N9—V14	116.8 (7)	O16—V14—N12	93.95 (13)
C10A—N9—V14	110.7 (3)	O15—V14—N12	92.87 (10)
C11A—C10A—N9	105.4 (5)	O7—V14—N12	156.46 (10)
C11A—C10A—H10A	110.7	O16—V14—N9	95.31 (12)
N9—C10A—H10A	110.7	O15—V14—N9	156.99 (11)
C11A—C10A—H10B	110.7	O7—V14—N9	84.96 (10)
N9—C10A—H10B	110.7	N12—V14—N9	76.64 (10)
H10A—C10A—H10B	108.8	O16—V14—O15ⁱ	171.43 (10)
N9—C10B—C11B	98.5 (15)	O15—V14—O15ⁱ	78.64 (8)
N9—C10B—H10C	112.1	O7—V14—O15ⁱ	83.83 (9)
C11B—C10B—H10C	112.1	N12—V14—O15ⁱ	78.44 (10)
N9—C10B—H10D	112.1	N9—V14—O15ⁱ	79.20 (9)
C11B—C10B—H10D	112.1	O16—V14—V14ⁱ	152.02 (10)
H10C—C10B—H10D	109.7	O15—V14—V14ⁱ	46.82 (7)
C10A—C11A—N12	107.1 (5)	O7—V14—V14ⁱ	90.10 (8)
C10A—C11A—H11A	110.3	N12—V14—V14ⁱ	82.99 (9)
N12—C11A—H11A	110.3	N9—V14—V14ⁱ	110.83 (8)
C10A—C11A—H11B	110.3	O15ⁱ—V14—V14ⁱ	31.82 (5)
N12—C11A—H11B	110.3	V14—O15—V14ⁱ	101.36 (8)

O7—C1—C2—C3	178.8 (3)	C11B—N12—V14—O16	−68.6 (10)
C6—C1—C2—C3	0.5 (5)	C13—N12—V14—O15	−72.6 (3)
O7—C1—C2—C8	0.1 (5)	C11A—N12—V14—O15	150.5 (4)
C6—C1—C2—C8	−178.2 (3)	C11B—N12—V14—O15	−174.8 (10)
C1—C2—C3—C4	−0.2 (6)	C13—N12—V14—O7	167.7 (3)
C8—C2—C3—C4	178.6 (4)	C11A—N12—V14—O7	30.8 (5)
C2—C3—C4—C5	0.1 (7)	C11B—N12—V14—O7	65.5 (10)
C3—C4—C5—C6	−0.5 (6)	C13—N12—V14—N9	128.1 (3)
C4—C5—C6—C1	0.8 (6)	C11A—N12—V14—N9	−8.8 (4)
O7—C1—C6—C5	−179.2 (3)	C11B—N12—V14—N9	26.0 (10)
C2—C1—C6—C5	−0.8 (5)	C13—N12—V14—O15ⁱ	−150.4 (3)
C6—C1—O7—V14	171.4 (2)	C11A—N12—V14—O15ⁱ	72.7 (4)
C2—C1—O7—V14	−6.9 (5)	C11B—N12—V14—O15ⁱ	107.4 (10)
C3—C2—C8—N9	−174.6 (4)	C13—N12—V14—V14ⁱ	−118.5 (2)
C1—C2—C8—N9	4.1 (6)	C11A—N12—V14—V14ⁱ	104.6 (4)
C2—C8—N9—C10B	153.2 (11)	C11B—N12—V14—V14ⁱ	139.4 (10)
C2—C8—N9—C10A	−176.4 (5)	C8—N9—V14—O16	−104.1 (3)
C2—C8—N9—V14	−2.2 (5)	C10B—N9—V14—O16	101.9 (12)
C8—N9—C10A—C11A	−135.7 (5)	C10A—N9—V14—O16	70.7 (4)
C10B—N9—C10A—C11A	−59.1 (15)	C8—N9—V14—O15	98.4 (4)
V14—N9—C10A—C11A	49.1 (7)	C10B—N9—V14—O15	−55.7 (12)
C8—N9—C10B—C11B	161.4 (12)	C10A—N9—V14—O15	−86.8 (5)
C10A—N9—C10B—C11B	44.5 (16)	C8—N9—V14—O7	−2.1 (3)
V14—N9—C10B—C11B	−40 (2)	C10B—N9—V14—O7	−156.2 (12)
N9—C10A—C11A—N12	−55.7 (8)	C10A—N9—V14—O7	172.7 (4)
N9—C10B—C11B—N12	63 (2)	C8—N9—V14—N12	163.1 (3)
C10A—C11A—N12—C13	−97.6 (6)	C10B—N9—V14—N12	9.0 (11)
C10A—C11A—N12—C11B	−44.7 (12)	C10A—N9—V14—N12	−22.1 (4)
C10A—C11A—N12—V14	38.2 (8)	C8—N9—V14—O15ⁱ	82.6 (3)
C10B—C11B—N12—C13	−175.1 (16)	C10B—N9—V14—O15ⁱ	−71.5 (11)
C10B—C11B—N12—C11A	50.5 (15)	C10A—N9—V14—O15ⁱ	−102.7 (4)
C10B—C11B—N12—V14	−58.4 (19)	C8—N9—V14—V14ⁱ	86.1 (3)
C1—O7—V14—O16	101.1 (3)	C10B—N9—V14—V14ⁱ	−68.0 (12)
C1—O7—V14—O15	−150.4 (3)	C10A—N9—V14—V14ⁱ	−99.1 (4)
C1—O7—V14—N12	−31.7 (5)	O16—V14—O15—V14ⁱ	−172.54 (11)
C1—O7—V14—N9	6.8 (3)	O7—V14—O15—V14ⁱ	81.85 (10)
C1—O7—V14—O15ⁱ	−72.9 (3)	N12—V14—O15—V14ⁱ	−77.60 (10)
C1—O7—V14—V14ⁱ	−104.1 (3)	N9—V14—O15—V14ⁱ	−15.9 (3)
C13—N12—V14—O16	33.6 (3)	O15ⁱ—V14—O15—V14ⁱ	0.0
C11A—N12—V14—O16	−103.3 (4)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O16ⁱⁱ	0.93	2.60	3.520 (4)	170
C11B—H11C···Cg1ⁱⁱⁱⁱⁱⁱ	0.97	2.82	3.47 (2)	124

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

Experimental details

Crystal data
Chemical formula	[V₂(C₁₀H₁₃N₂O)₂O₄]
M_r	520.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.6801 (2), 11.9955 (6), 13.8643 (7)
β (°)	92.156 (4)
V (Å³)	1110.18 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.6 × 0.1 × 0.1

Data collection
Diffractometer	Oxford Diffraction Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.532, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	6336, 1960, 1288
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 0.90
No. of reflections	1960
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.39

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected bond lengths (Å) top

O7—V14	1.926 (2)	V14—O16	1.612 (2)
N9—V14	2.158 (3)	V14—O15	1.674 (2)
N12—V14	2.146 (3)	V14—O15ⁱ	2.316 (2)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O16ⁱⁱ	0.93	2.60	3.520 (4)	170
C11B—H11C···Cg1ⁱⁱⁱⁱⁱⁱ	0.97	2.82	3.47 (2)	124

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

Acknowledgements

The Polish Ministry of Science and Higher Education under grants BW/8000-5-0462-8 and DS/8210-40-086-8 financially supported this work.

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