{2-[1-(2-Amino-2-methyl­propyl­imino)eth­yl]phenolato-κ3N,N′,O}dioxidovanadium(V)

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

doi:10.1107/S1600536808042839

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m190

doi:10.1107/S1600536808042839

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{2-[1-(2-Amino-2-methylpropylimino)ethyl]phenolato-κ³N,N′,O}dioxidovanadium(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 10 December 2008; accepted 16 December 2008; online 14 January 2009)

In the crystal structure of the title compound, [V(C₁₂H₁₇N₂O)O₂], the vanadium(V) centre is five-coordinate in a distorted square-pyramidal environment. The three atoms of the deprotonated Schiff base and a double-bonded O atom comprise the basal plane. N—H⋯O hydrogen bonds lead to a zigzag chain structure parallel to [001].

Related literature

For general background, see: Carter-Franklin et al. (2003 ); Eady (2003 ); Evangelou (2002 ); Mendz (1991 ); Mokry & Carrano (1993 ); Parekh et al. (2006 ); Rehder et al. (2002 , 2003 ); Shahzadi et al. (2007 ). For related structures, see: Kwiatkowski et al. (2003 , 2007 ); Rao et al. (1981 ). For synthesis, see: Kwiatkowski et al. (2003). For the calculation of square-pyramidal geometries, see: Holmes (1984 ).

Experimental

Crystal data

[V(C₁₂H₁₇N₂O)O₂]
M_r = 288.22
Orthorhombic, P n a 2₁
a = 11.1198 (6) Å
b = 15.7408 (8) Å
c = 7.6448 (3) Å
V = 1338.10 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 295 (2) K
0.20 × 0.04 × 0.04 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.941, T_max = 0.964
11574 measured reflections
2126 independent reflections
1387 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.051
S = 0.83
2126 reflections
167 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 849 Friedel pairs
Flack parameter: 0.23 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11A⋯O14ⁱ	0.90	2.08	2.942 (4)	159
N11—H11B⋯O15ⁱⁱ	0.90	2.29	3.173 (4)	168
Symmetry codes: (i) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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/S1600536808042839/ng2526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042839/ng2526Isup2.hkl

checkCIF report

Comment top

Vanadium(IV) and (V) complexes with Schiff bases are excellent model compounds for some biological enzymes, viz.: haloperoxidases (Carter-Franklin et al., 2003; Rehder et al., 2003), phosphomutases (Mendz, 1991) and nitrogenases (Eady, 2003). Their various pharmocological properties also has been reported, especially as an antidiabetes (Rehder et al., 2002), anticancer (Evangelou, 2002), antifungal and antibacterial (Parekh et al., 2006; Shahzadi et al., 2007) agents.

The crystal structure of (I) consists of monomeric complex molecules (Fig. 1) with a distorted square pyramidal geometry about vanadium with O15 at the apex. By the use of the dihedral angle method and the unit bond lengths, it was estimated that the structure is displaced by 76.1% along the Berry coordinate from the ideal trigonal bipyramidal (0%) toward the ideal square pyramidal (100%) geometry (Holmes, 1984). In contrast to this structure, the similar monomeric complex, but derived from 4,6-dimetoxysalicylaldehyde (Kwiatkowski et al., 2003), reveals a distorted trigonal bipyramidal environment with the degree of the distortion of 41.2% along the Berry coordinate. The vanadium atom is displaced from the mean plane passing through the four basal atoms, N8, N11, O13 and O14, by ca 0.51 (1) Å towards O15. The bond lengths V12—N8 of 2.171 (3) Å, V12—N11 of 2.118 (2) Å, V12—O13 of 1.883 (2) Å, V12—O14 of 1.635 (2) Å, V12—O15 of 1.615 (2) Å and the O=V=O angle of 109.9° are similar to the values in other cis-VO₂⁺ complexes (Mokry & Carrano, 1993; Kwiatkowski et al., 2003; Kwiatkowski et al., 2007). The six-membered chelate ring (V12, O13, C1, C2, C7, N8) is concluded to be an envelope on V12 atom. The ring puckering analysis shows that the five-membered chelate ring defined by V12, N11, C10, C9, N8 atoms adopts a twisted conformation on C10 and N11 atoms, with P = 282.7 (2)° and Tau₍_M₎ = 49.9 (2)° for reference bond V12—N8 (Rao et al., 1981).

The crystal structure of the monomeric complex (I) is stabilized by the C—H···O, N—H···O hydrogen bonds and C—H···π interactions. Hydrogen bonds between dioxidovanadium oxygen atoms and nitrogen and carbon atoms of neighbouring molecules result in formation of infinite chains and closed loops, extending in the a direction (Tables 1 and 2, Fig. 2).

Related literature top

For general background, see: Carter-Franklin et al. (2003); Eady (2003); Evangelou (2002); Mendz (1991); Mokry & Carrano (1993); Parekh et al. (2006); Rehder et al. (2002, 2003); Shahzadi et al. (2007). For related structures, see: Kwiatkowski et al. (2003, 2007); Rao et al. (1981). For synthesis, see: Kwiatkowski et al. (2003). For the calculation of square-pyramidal geometries, see: Holmes (1984).

Experimental top

The complex (I) were obtained in a template/complexation reactions analogous to those described for preparation of dioxidovanadium(V) complexes with Schiff base ligands (Kwiatkowski et al., 2003). A solution of 1 mmol of 2-methyl-1,2-diaminopropane 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. 2-Acetylphenol (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 and dried over molecular sieves.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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 complex (I), with displacement ellipsoids drawn at the 25% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The arrangement of the molecules of (I) in the crystal structure viewed approximately along a axis. The C—H···O and N—H···O hydrogen bonds are represented by dashed lines and the C—H···π interactions are represented by dotted lines.

{2-[1-(2-Amino-2-methylpropylimino)ethyl]phenolato- κ³N,N',O}dioxidovanadium(V) top

Crystal data top

[V(C₁₂H₁₇N₂O)O₂]	F(000) = 600
M_r = 288.22	D_x = 1.431 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2126 reflections
a = 11.1198 (6) Å	θ = 3.2–25.1°
b = 15.7408 (8) Å	µ = 0.74 mm⁻¹
c = 7.6448 (3) Å	T = 295 K
V = 1338.10 (11) Å³	Needle, white
Z = 4	0.2 × 0.04 × 0.04 mm

Data collection top

Oxford Diffraction Ruby CCD diffractometer	2126 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.1°, θ_min = 3.2°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −18→18
T_min = 0.941, T_max = 0.964	l = −9→7
11574 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.051	w = 1/[σ²(F_o²) + (0.0211P)²] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max < 0.001
2126 reflections	Δρ_max = 0.19 e Å⁻³
167 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.23 (2)

Crystal data top

[V(C₁₂H₁₇N₂O)O₂]	V = 1338.10 (11) Å³
M_r = 288.22	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.1198 (6) Å	µ = 0.74 mm⁻¹
b = 15.7408 (8) Å	T = 295 K
c = 7.6448 (3) Å	0.2 × 0.04 × 0.04 mm

Data collection top

Oxford Diffraction Ruby CCD diffractometer	2126 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	1387 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.964	R_int = 0.071
11574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.051	Δρ_max = 0.19 e Å⁻³
S = 0.83	Δρ_min = −0.16 e Å⁻³
2126 reflections	Absolute structure: Flack (1983), 849 Friedel pairs
167 parameters	Absolute structure parameter: 0.23 (2)
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.3317 (3)	0.3973 (2)	0.5333 (4)	0.0380 (8)
C2	0.2695 (3)	0.37563 (19)	0.6865 (4)	0.0354 (8)
C3	0.3314 (3)	0.37812 (17)	0.8474 (6)	0.0512 (8)
H3A	0.2903	0.3651	0.9499	0.061*
C4	0.4498 (3)	0.3992 (2)	0.8561 (6)	0.0560 (10)
H4A	0.4887	0.4012	0.9637	0.067*
C5	0.5121 (3)	0.4175 (2)	0.7045 (6)	0.0602 (11)
H5A	0.5931	0.4319	0.7101	0.072*
C6	0.4544 (3)	0.4145 (2)	0.5448 (5)	0.0510 (10)
H6A	0.4982	0.4240	0.4431	0.061*
C7	0.1437 (3)	0.34815 (19)	0.6801 (4)	0.0399 (8)
N8	0.0753 (2)	0.36544 (15)	0.5463 (3)	0.0378 (7)
C9	−0.0510 (3)	0.3371 (2)	0.5463 (4)	0.0422 (9)
H9A	−0.0956	0.3677	0.6353	0.051*
H9B	−0.0549	0.2770	0.5733	0.051*
C10	−0.1063 (3)	0.3534 (2)	0.3683 (4)	0.0407 (9)
N11	−0.06106 (19)	0.44045 (15)	0.3205 (5)	0.0408 (6)
H11A	−0.0946	0.4790	0.3925	0.049*
H11B	−0.0844	0.4528	0.2107	0.049*
V12	0.12859 (4)	0.45059 (3)	0.33674 (6)	0.03758 (15)
O13	0.27910 (18)	0.39910 (13)	0.3758 (3)	0.0456 (6)
O14	0.1359 (2)	0.45725 (14)	0.1236 (2)	0.0467 (6)
O15	0.1372 (2)	0.54432 (13)	0.4218 (2)	0.0483 (6)
C26	0.0950 (3)	0.29854 (18)	0.8337 (6)	0.0592 (9)
H26A	0.0162	0.2776	0.8060	0.089*
H26B	0.0905	0.3349	0.9343	0.089*
H26C	0.1474	0.2516	0.8584	0.089*
C27	−0.0620 (3)	0.2904 (2)	0.2305 (5)	0.0536 (9)
H27A	0.0243	0.2886	0.2320	0.080*
H27B	−0.0890	0.3081	0.1170	0.080*
H27C	−0.0933	0.2349	0.2559	0.080*
C28	−0.2434 (3)	0.3536 (2)	0.3770 (5)	0.0699 (12)
H28A	−0.2697	0.3960	0.4587	0.105*
H28B	−0.2713	0.2988	0.4143	0.105*
H28C	−0.2756	0.3661	0.2633	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.0260 (19)	0.049 (2)	0.0093 (17)	0.0054 (19)	0.0025 (17)
C2	0.041 (2)	0.0303 (19)	0.035 (2)	0.0077 (17)	0.0034 (17)	−0.0038 (16)
C3	0.064 (2)	0.0462 (19)	0.043 (2)	0.0081 (17)	0.007 (3)	0.005 (3)
C4	0.058 (3)	0.056 (2)	0.054 (3)	0.0082 (19)	−0.009 (3)	−0.016 (3)
C5	0.039 (2)	0.053 (3)	0.089 (3)	−0.0058 (19)	−0.002 (3)	−0.005 (2)
C6	0.050 (3)	0.051 (2)	0.052 (2)	0.001 (2)	0.009 (2)	0.003 (2)
C7	0.056 (2)	0.0311 (19)	0.033 (2)	0.0004 (19)	0.0127 (18)	−0.0038 (14)
N8	0.0384 (19)	0.0394 (17)	0.0355 (16)	0.0009 (14)	0.0112 (14)	−0.0026 (14)
C9	0.053 (3)	0.039 (2)	0.0346 (19)	−0.0049 (19)	0.0174 (18)	−0.0038 (17)
C10	0.038 (2)	0.0445 (19)	0.040 (2)	−0.0079 (17)	0.0074 (17)	−0.0095 (18)
N11	0.0423 (14)	0.0400 (14)	0.0400 (13)	0.0048 (13)	−0.0037 (18)	−0.0058 (18)
V12	0.0404 (3)	0.0357 (3)	0.0366 (3)	0.0011 (3)	0.0062 (4)	0.0047 (4)
O13	0.0417 (13)	0.0517 (14)	0.0434 (17)	0.0064 (10)	0.0104 (11)	0.0074 (12)
O14	0.0508 (14)	0.0579 (14)	0.0315 (11)	0.0065 (16)	0.0078 (11)	0.0070 (11)
O15	0.0559 (16)	0.0353 (13)	0.0538 (12)	−0.0029 (13)	0.0005 (11)	−0.0044 (11)
C26	0.082 (3)	0.0554 (19)	0.0399 (16)	−0.0127 (18)	0.015 (3)	0.005 (3)
C27	0.067 (2)	0.047 (2)	0.0469 (18)	−0.008 (2)	0.013 (2)	−0.007 (2)
C28	0.046 (2)	0.085 (3)	0.078 (3)	−0.017 (2)	0.004 (2)	−0.004 (3)

Geometric parameters (Å, º) top

C1—O13	1.339 (4)	C10—N11	1.504 (4)
C1—C6	1.393 (5)	C10—C28	1.527 (4)
C1—C2	1.402 (4)	C10—C27	1.529 (4)
C2—C3	1.410 (5)	N11—V12	2.118 (2)
C2—C7	1.465 (4)	N11—H11A	0.9000
C3—C4	1.359 (4)	N11—H11B	0.9000
C3—H3A	0.9300	V12—O15	1.6151 (19)
C4—C5	1.380 (5)	V12—O14	1.6352 (18)
C4—H4A	0.9300	V12—O13	1.883 (2)
C5—C6	1.380 (4)	C26—H26A	0.9600
C5—H5A	0.9300	C26—H26B	0.9600
C6—H6A	0.9300	C26—H26C	0.9600
C7—N8	1.304 (4)	C27—H27A	0.9600
C7—C26	1.510 (4)	C27—H27B	0.9600
N8—C9	1.473 (4)	C27—H27C	0.9600
N8—V12	2.171 (3)	C28—H28A	0.9600
C9—C10	1.515 (4)	C28—H28B	0.9600
C9—H9A	0.9700	C28—H28C	0.9600
C9—H9B	0.9700

O13—C1—C6	118.7 (3)	C10—N11—V12	112.76 (17)
O13—C1—C2	122.7 (3)	C10—N11—H11A	109.0
C6—C1—C2	118.5 (3)	V12—N11—H11A	109.0
C1—C2—C3	118.7 (3)	C10—N11—H11B	109.0
C1—C2—C7	121.0 (3)	V12—N11—H11B	109.0
C3—C2—C7	120.2 (3)	H11A—N11—H11B	107.8
C4—C3—C2	121.5 (4)	O15—V12—O14	109.85 (10)
C4—C3—H3A	119.2	O15—V12—O13	106.06 (11)
C2—C3—H3A	119.2	O14—V12—O13	98.12 (10)
C3—C4—C5	119.7 (4)	O15—V12—N11	98.71 (11)
C3—C4—H4A	120.1	O14—V12—N11	89.77 (13)
C5—C4—H4A	120.1	O13—V12—N11	149.49 (10)
C6—C5—C4	120.1 (4)	O15—V12—N8	106.46 (9)
C6—C5—H5A	119.9	O14—V12—N8	142.05 (11)
C4—C5—H5A	119.9	O13—V12—N8	81.94 (9)
C5—C6—C1	121.2 (3)	N11—V12—N8	74.05 (12)
C5—C6—H6A	119.4	C1—O13—V12	122.65 (18)
C1—C6—H6A	119.4	C7—C26—H26A	109.5
N8—C7—C2	121.4 (3)	C7—C26—H26B	109.5
N8—C7—C26	120.6 (3)	H26A—C26—H26B	109.5
C2—C7—C26	118.0 (3)	C7—C26—H26C	109.5
C7—N8—C9	119.5 (3)	H26A—C26—H26C	109.5
C7—N8—V12	123.3 (2)	H26B—C26—H26C	109.5
C9—N8—V12	116.56 (19)	C10—C27—H27A	109.5
N8—C9—C10	109.6 (2)	C10—C27—H27B	109.5
N8—C9—H9A	109.8	H27A—C27—H27B	109.5
C10—C9—H9A	109.8	C10—C27—H27C	109.5
N8—C9—H9B	109.8	H27A—C27—H27C	109.5
C10—C9—H9B	109.8	H27B—C27—H27C	109.5
H9A—C9—H9B	108.2	C10—C28—H28A	109.5
N11—C10—C9	103.7 (3)	C10—C28—H28B	109.5
N11—C10—C28	110.0 (2)	H28A—C28—H28B	109.5
C9—C10—C28	111.5 (3)	C10—C28—H28C	109.5
N11—C10—C27	108.4 (3)	H28A—C28—H28C	109.5
C9—C10—C27	112.2 (3)	H28B—C28—H28C	109.5
C28—C10—C27	110.7 (3)

O13—C1—C2—C3	−178.0 (3)	N8—C9—C10—C27	74.2 (3)
C6—C1—C2—C3	4.6 (4)	C9—C10—N11—V12	53.3 (3)
O13—C1—C2—C7	4.0 (4)	C28—C10—N11—V12	172.7 (2)
C6—C1—C2—C7	−173.4 (3)	C27—C10—N11—V12	−66.2 (3)
C1—C2—C3—C4	−1.5 (4)	C10—N11—V12—O15	−139.7 (2)
C7—C2—C3—C4	176.6 (3)	C10—N11—V12—O14	110.2 (3)
C2—C3—C4—C5	−0.9 (5)	C10—N11—V12—O13	4.5 (4)
C3—C4—C5—C6	0.0 (5)	C10—N11—V12—N8	−35.0 (2)
C4—C5—C6—C1	3.4 (6)	C7—N8—V12—O15	−66.8 (3)
O13—C1—C6—C5	176.9 (3)	C9—N8—V12—O15	103.9 (2)
C2—C1—C6—C5	−5.6 (5)	C7—N8—V12—O14	130.5 (2)
C1—C2—C7—N8	−20.0 (4)	C9—N8—V12—O14	−58.7 (3)
C3—C2—C7—N8	162.0 (3)	C7—N8—V12—O13	37.6 (2)
C1—C2—C7—C26	159.8 (3)	C9—N8—V12—O13	−151.6 (2)
C3—C2—C7—C26	−18.2 (4)	C7—N8—V12—N11	−161.4 (3)
C2—C7—N8—C9	−179.5 (3)	C9—N8—V12—N11	9.3 (2)
C26—C7—N8—C9	0.8 (4)	C6—C1—O13—V12	−136.7 (2)
C2—C7—N8—V12	−9.0 (4)	C2—C1—O13—V12	45.9 (4)
C26—C7—N8—V12	171.2 (2)	O15—V12—O13—C1	50.2 (2)
C7—N8—C9—C10	−172.0 (3)	O14—V12—O13—C1	163.6 (2)
V12—N8—C9—C10	16.9 (3)	N11—V12—O13—C1	−92.8 (3)
N8—C9—C10—N11	−42.6 (3)	N8—V12—O13—C1	−54.7 (2)
N8—C9—C10—C28	−161.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O14ⁱ	0.90	2.08	2.942 (4)	159
N11—H11B···O15ⁱⁱ	0.90	2.29	3.173 (4)	168
C26—H26B···O14ⁱⁱⁱ	0.96	2.46	3.370 (4)	158

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

Experimental details

Crystal data
Chemical formula	[V(C₁₂H₁₇N₂O)O₂]
M_r	288.22
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	11.1198 (6), 15.7408 (8), 7.6448 (3)
V (Å³)	1338.10 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.2 × 0.04 × 0.04

Data collection
Diffractometer	Oxford Diffraction Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.941, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	11574, 2126, 1387
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.051, 0.83
No. of reflections	2126
No. of parameters	167
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16
Absolute structure	Flack (1983), 849 Friedel pairs
Absolute structure parameter	0.23 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O14ⁱ	0.90	2.08	2.942 (4)	159
N11—H11B···O15ⁱⁱ	0.90	2.29	3.173 (4)	168

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

Acknowledgements

This scientific work has been supported by Funds for Science in Years 2007–2009 as a research project (N N204 0355 33 and DS/8210–4–0086–9).

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