Bis(acetyl­acetonato-κ2O,O′)(2-amino-1-methyl-1H-benzimidazole-κN3)oxido­vanadium(IV)

Kadirova, Z.C.; Rahmonova, D.S.; Talipov, S.A.; Ashurov, J.M.; Parpiev, N.A.

doi:10.1107/S1600536809023113

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m819

doi:10.1107/S1600536809023113

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Bis(acetylacetonato-κ²O,O′)(2-amino-1-methyl-1H-benzimidazole-κN³)oxidovanadium(IV)

Zukhra Ch. Kadirova,^a ^* Dilnoza S. Rahmonova,^a Samat A. Talipov,^b Jamshid M. Ashurov ^b and Nusrat A. Parpiev ^a

^aNational University of Uzbekistan, Tashkent 100123, Uzbekistan, and ^bInstitute of Biorganic Chemistry, Mirzo-Ulugbek St. 83, Tashkent 100125, Uzbekistan
^*Correspondence e-mail: zuhra_kadirova@yahoo.com

(Received 5 May 2009; accepted 16 June 2009; online 24 June 2009)

The title mixed-ligand oxidovanadium(IV) compound, [VO(C₅H₇O₂)₂(C₈H₉N₃)], contains a V^IV atom in a distorted octahedral coordination, which is typical for such complexes. The vanadyl group and the N-heterocyclic ligand are cis to each other. The coordination bond is located at the endocyclic N atom of the benzimidazole ligand. Intramolecular hydrogen bonds between the exo-NH₂ group H atoms and acetylacetonate O atoms stabilize the crystal structure.

Related literature

For the activity of vanadium complexes, see: Rehder (1999 ). For the crystal structures of acetylacetonate and benzimidazole oxidovanadium(IV) and (V) complexes, see: Maurya (2002 ); Caira et al. (1972 ); Shao et al. (1984 ); Crans et al. (1997 ); Maurya et al. (2006 ); Akhmed et al. (2004 ). For 1-methyl- 2-aminobenzimidazole compounds, see: Borodkina et al. (2003 ); Chekhlov (2004 ).

Experimental

Crystal data

[V(C₅H₇O₂)₂O(C₈H₉N₃)]
M_r = 412.33
Monoclinic, P 2₁ /n
a = 8.27120 (10) Å
b = 15.0472 (2) Å
c = 16.1078 (2) Å
β = 104.2646 (14)°
V = 1942.94 (4) Å³
Z = 4
Cu Kα radiation
μ = 4.57 mm⁻¹
T = 293 K
0.25 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlisPro. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.544, T_max = 0.694
8892 measured reflections
3720 independent reflections
2983 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.106
S = 1.00
3720 reflections
249 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3AA⋯O2B	0.86	2.38	2.972 (3)	127
N3A—H3AA⋯O2C	0.86	2.47	3.034 (2)	124

Data collection: CrysAlisPro (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlisPro. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023113/su2113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023113/su2113Isup2.hkl

checkCIF report

Comment top

Vanadium complexes have attracted interest in recent nears due to their insulin-mimetic action, and to their activity in nitrogen fixation and haloperoxidation (Rehder, 1999). The vanadium atom can have different coordination numbers and forms coordination compounds with a variety of coordination geometries and oxidation states (Maurya, 2002). Limited information is available on the crystal structure of the vanadium complexes of substituted benzimidazoles (Crans et al., 1997; Maurya et al., 2006). Bis(acetylacetonato)oxovanadium, [VO(acac)₂], is a common precursor for the synthesis of the mixed ligand vanadium(IV) and vanadium(V) complexes with the N-containing monodentate ligands (L), [VO(acac)₂L]. Usually these bis-chelated complexes can be cis- or trans- with distorted octahedral configurations (Caira et al., 1972; Shao et al., 1984). In this study, we prepared the mixed-ligand complex of oxovanadium(IV) with bidentate acetylacetonate and the monodentate benzimidazole, 2-amino-1-methylbenzimidazole, and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1, and geometrical parameters are available from the archived CIF. In this cis-complex, [VO(acac)₂L], the metal center has a slightly distorted octahedral N₁O₅ coordination sphere, assembled by the O—O-donor acetylacetonate, the oxo-group and the pyridine N-atom of the benzimidazole. The angles around the vanadium atom deviate from 90°, being in the range of 80.85 (6) - 99.91 (7) °, and from 180°, being in the range of 164.96 (7) - 179.18 (7)°, due to coordination of the sterically large ligand to the five-coordinate square-pyramidal [VO(acac)₂] complex (Akhmed et al., 2004).

The coordination bond is localized at the endo-cyclic N-atom of the benzimidazole ligand and the bond lengths and angles are similar to those reported for 2-amino-1-methylbenzimidazolium chloride hydrate (Borodkina et al., 2003), and bis(2-amino-1-methylbenzimidazole-N) dichlorocobalt(II) (Chekhlov et al., 2004). The amino-group is coplanar with the methyl-group [torsion angle C8A—N2A—C7A—N3A is 4.3 (4)°] and participates in intramolecular hydrogen bonds with the carbonyl O-atoms (Fig.2 and Table 1).

The V—O bond (V1—O2B) trans to the oxo-group is significally longer (2.1523 (17) Å) than the V—O bonds which are cis to the oxo-group (1.9927 (14) - 2.0139 (14) Å). In contrast the carbonyl bond involving atom O2B (C4B?O2B) is shorter, (1.252 (3) Å), than the other acetylacetonate C?O bonds [1.264 (3) - 1.273 (3) Å]. The V—N bond length, the cis- and trans- V—O bond lengths are comparable to those reported for oxovanadium(IV) species containing acac^- as ligand in a similar orientation (Crans et al., 1997).

Related literature top

For the activity of vanadium complexes, see: Rehder (1999). For the crystal structure of bis(acetylacetonato)-2-amino-1-methylbenzimidazole oxovanadium(IV) [VO(C₅H₇O₂)₂(C₈H₉N₃)], see: Maurya (2002). For vanadium(IV) and (V) compounds, see: Caira et al. (1972; Shao et al. (1984); Crans et al. (1997; Maurya et al. (2006); Akhmed et al. (2004); Borodkina et al. (2003); Chekhlov et al. (2004).

Experimental top

Equimolar quantities of [VO(acac)₂] (acac = acetnlacetonate) and 2-amine-1-methylbenzimidazole (0.53 g, 1.9 mmol) were refluxed in ethanol for 3 h. The resulting green solution yielded green crystals which were filtered off and washed twice with acetone. Elem. Analysis found: C 52.4, H 6.0, N 10.3, V 12.4%; C₁₈H₂₃N₃O₅V requires: C 52.4, H 5.6, N 10.2,V 12.4%. IR (BRUKER spectrometer, KBr, cm^-1): 3415 s, 3326 s, 1641 s, 1591 s, 1556 s, 1462m, 1373 s, 1273m, 1018m, 1252w, 1198w, 1132w,1052m, 983m, 939m, 787w, 746m, 669w, 590w, 557w, 455w). Crystals of the title compound, suitable X-ray diffraction analysis, were selected directly from the sample as prepared.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecuar structure of the title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the crystal packing of the title compound, with the intramolecuéar N—H···O hydrogen bonds shown as pale blue dashed lines (see Table 1 for details).

Bis(acetylacetonato-κ²O,O')(2-amino-1-methyl-1H- benzimidazole-κN³)oxidovanadium(IV) top

Crystal data top

[V(C₅H₇O₂)₂O(C₈H₉N₃)]	F(000) = 860
M_r = 412.33	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3720 reflections
a = 8.2712 (1) Å	θ = 4.1–76.0°
b = 15.0472 (2) Å	µ = 4.57 mm⁻¹
c = 16.1078 (2) Å	T = 293 K
β = 104.2646 (14)°	Monoclinic, green
V = 1942.94 (4) Å³	0.25 × 0.12 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer	2983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 76.0°, θ_min = 4.1°
heavy atom scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −18→17
T_min = 0.544, T_max = 0.694	l = −20→20
8892 measured reflections	3 standard reflections every 120 reflections
3720 independent reflections	intensity decay: none

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0695P)²] where P = (F_o² + 2F_c²)/3
3720 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[V(C₅H₇O₂)₂O(C₈H₉N₃)]	V = 1942.94 (4) Å³
M_r = 412.33	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 8.2712 (1) Å	µ = 4.57 mm⁻¹
b = 15.0472 (2) Å	T = 293 K
c = 16.1078 (2) Å	0.25 × 0.12 × 0.08 mm
β = 104.2646 (14)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2983 reflections with I > 2σ(I)
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	R_int = 0.028
T_min = 0.544, T_max = 0.694	3 standard reflections every 120 reflections
8892 measured reflections	intensity decay: none
3720 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
3720 reflections	Δρ_min = −0.23 e Å⁻³
249 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
V1	0.72939 (4)	0.84139 (2)	0.15879 (2)	0.0439 (1)
O1B	0.85987 (19)	0.94296 (8)	0.22441 (9)	0.0495 (5)
O1C	0.7792 (2)	0.89026 (9)	0.05202 (9)	0.0572 (5)
O1V	0.5517 (2)	0.88731 (10)	0.14793 (10)	0.0590 (5)
O2B	0.9707 (2)	0.78057 (10)	0.17502 (10)	0.0556 (5)
O2C	0.6598 (2)	0.72797 (9)	0.09633 (9)	0.0559 (5)
N1A	0.7312 (2)	0.77605 (10)	0.27641 (10)	0.0450 (5)
N2A	0.7430 (3)	0.67520 (11)	0.37942 (11)	0.0579 (7)
N3A	0.8363 (3)	0.63142 (12)	0.25875 (13)	0.0667 (8)
C1A	0.6736 (3)	0.81453 (13)	0.34241 (12)	0.0475 (6)
C1B	1.0649 (4)	1.03962 (17)	0.3018 (2)	0.0777 (10)
C1C	0.7707 (5)	0.9161 (2)	−0.09262 (17)	0.0869 (13)
C2A	0.6149 (3)	0.89931 (15)	0.35119 (14)	0.0577 (8)
C2B	1.0157 (3)	0.95299 (13)	0.25591 (12)	0.0497 (7)
C2C	0.7364 (3)	0.85815 (15)	−0.02274 (15)	0.0574 (8)
C3A	0.5629 (4)	0.91763 (18)	0.42447 (17)	0.0732 (10)
C3B	1.1380 (3)	0.89314 (15)	0.25154 (17)	0.0630 (8)
C3C	0.6646 (4)	0.77473 (16)	−0.04198 (15)	0.0637 (8)
C4A	0.5667 (5)	0.8537 (2)	0.48746 (18)	0.0844 (13)
C4B	1.1117 (3)	0.80980 (14)	0.21204 (13)	0.0505 (7)
C4C	0.6354 (3)	0.71403 (14)	0.01637 (14)	0.0523 (7)
C5A	0.6251 (4)	0.76985 (18)	0.47967 (16)	0.0768 (12)
C5B	1.2601 (3)	0.75171 (16)	0.21416 (18)	0.0698 (9)
C5C	0.5724 (4)	0.62284 (17)	−0.01264 (17)	0.0725 (9)
C6A	0.6788 (3)	0.75212 (14)	0.40690 (13)	0.0562 (7)
C7A	0.7706 (3)	0.69247 (13)	0.30215 (13)	0.0504 (7)
C8A	0.7863 (4)	0.59453 (16)	0.43059 (17)	0.0768 (9)
H3AA	0.85610	0.64500	0.21040	0.0800*
H3AB	0.85830	0.57890	0.27940	0.0800*
H2AA	0.61060	0.94230	0.30920	0.0690*
H3AC	0.52420	0.97440	0.43200	0.0880*
H4A	0.52880	0.86830	0.53550	0.1020*
H5AA	0.62850	0.72680	0.52150	0.0920*
H8AA	0.86740	0.56120	0.41000	0.1150*
H8AB	0.68810	0.55900	0.42600	0.1150*
H8AC	0.83190	0.61030	0.48950	0.1150*
H1BA	1.04180	1.08760	0.26140	0.1170*
H1BB	1.18190	1.03870	0.32930	0.1170*
H1BC	1.00230	1.04780	0.34420	0.1170*
H3BA	1.24760	0.90920	0.27690	0.0750*
H5BA	1.22290	0.69420	0.19160	0.1050*
H5BB	1.32470	0.74570	0.27220	0.1050*
H5BC	1.32750	0.77810	0.18010	0.1050*
H1CA	0.87820	0.94350	−0.07300	0.1300*
H1CB	0.68650	0.96130	−0.10720	0.1300*
H1CC	0.76940	0.88050	−0.14220	0.1300*
H3CA	0.63350	0.75860	−0.09950	0.0760*
H5CA	0.65170	0.57920	0.01560	0.1090*
H5CB	0.55760	0.61810	−0.07350	0.1090*
H5CC	0.46750	0.61290	0.00140	0.1090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0518 (2)	0.0385 (2)	0.0396 (2)	−0.0028 (1)	0.0080 (1)	−0.0025 (1)
O1B	0.0574 (9)	0.0391 (7)	0.0499 (8)	−0.0030 (6)	0.0091 (6)	−0.0053 (6)
O1C	0.0787 (11)	0.0472 (8)	0.0483 (8)	−0.0081 (7)	0.0207 (7)	−0.0005 (6)
O1V	0.0571 (10)	0.0618 (9)	0.0548 (9)	0.0055 (7)	0.0073 (7)	0.0089 (7)
O2B	0.0558 (10)	0.0477 (8)	0.0632 (9)	0.0019 (6)	0.0144 (7)	−0.0092 (6)
O2C	0.0729 (11)	0.0472 (8)	0.0433 (7)	−0.0124 (7)	0.0063 (7)	−0.0051 (6)
N1A	0.0543 (10)	0.0383 (8)	0.0401 (8)	−0.0030 (7)	0.0071 (7)	−0.0021 (6)
N2A	0.0848 (15)	0.0398 (9)	0.0435 (9)	−0.0063 (9)	0.0054 (9)	0.0015 (7)
N3A	0.0966 (17)	0.0426 (9)	0.0608 (12)	0.0106 (10)	0.0193 (11)	−0.0009 (8)
C1A	0.0541 (13)	0.0442 (10)	0.0409 (10)	−0.0077 (9)	0.0053 (8)	−0.0041 (8)
C1B	0.084 (2)	0.0505 (13)	0.0874 (19)	−0.0150 (12)	0.0000 (15)	−0.0131 (12)
C1C	0.130 (3)	0.0822 (18)	0.0595 (15)	−0.0136 (18)	0.0444 (16)	−0.0004 (13)
C2A	0.0689 (15)	0.0514 (12)	0.0503 (12)	0.0024 (10)	0.0097 (10)	−0.0021 (9)
C2B	0.0621 (14)	0.0430 (10)	0.0415 (10)	−0.0093 (9)	0.0083 (9)	0.0022 (8)
C2C	0.0703 (16)	0.0576 (13)	0.0494 (11)	0.0073 (11)	0.0246 (10)	−0.0027 (9)
C3A	0.097 (2)	0.0639 (15)	0.0623 (14)	0.0086 (14)	0.0263 (14)	−0.0116 (12)
C3B	0.0499 (14)	0.0591 (13)	0.0736 (15)	−0.0065 (10)	0.0033 (11)	−0.0042 (11)
C3C	0.0863 (18)	0.0616 (14)	0.0451 (11)	−0.0049 (12)	0.0199 (11)	−0.0113 (10)
C4A	0.121 (3)	0.087 (2)	0.0534 (14)	−0.0039 (17)	0.0369 (16)	−0.0130 (13)
C4B	0.0537 (13)	0.0511 (11)	0.0477 (10)	0.0020 (9)	0.0146 (9)	0.0085 (8)
C4C	0.0554 (13)	0.0492 (11)	0.0489 (11)	0.0013 (9)	0.0064 (9)	−0.0105 (9)
C5A	0.118 (3)	0.0664 (16)	0.0471 (12)	−0.0123 (15)	0.0222 (14)	0.0000 (11)
C5B	0.0621 (17)	0.0719 (16)	0.0744 (16)	0.0144 (12)	0.0150 (13)	0.0031 (12)
C5C	0.095 (2)	0.0597 (14)	0.0575 (14)	−0.0135 (13)	0.0088 (13)	−0.0165 (11)
C6A	0.0747 (16)	0.0492 (11)	0.0415 (10)	−0.0104 (10)	0.0083 (10)	−0.0029 (8)
C7A	0.0606 (14)	0.0395 (10)	0.0462 (10)	−0.0023 (9)	0.0038 (9)	−0.0032 (8)
C8A	0.115 (2)	0.0467 (12)	0.0609 (14)	−0.0096 (13)	0.0069 (15)	0.0115 (10)

Geometric parameters (Å, º) top

V1—O1B	2.0139 (14)	C3C—C4C	1.374 (3)
V1—O1C	2.0044 (15)	C4A—C5A	1.368 (4)
V1—O1V	1.5942 (17)	C4B—C5B	1.500 (3)
V1—O2B	2.1523 (17)	C4C—C5C	1.501 (3)
V1—O2C	1.9927 (14)	C5A—C6A	1.378 (4)
V1—N1A	2.1313 (16)	C1B—H1BA	0.9600
O1B—C2B	1.273 (3)	C1B—H1BB	0.9600
O1C—C2C	1.264 (3)	C1B—H1BC	0.9600
O2B—C4B	1.252 (3)	C1C—H1CA	0.9600
O2C—C4C	1.271 (3)	C1C—H1CB	0.9600
N1A—C1A	1.394 (3)	C1C—H1CC	0.9600
N1A—C7A	1.339 (2)	C2A—H2AA	0.9300
N2A—C6A	1.391 (3)	C3A—H3AC	0.9300
N2A—C7A	1.345 (3)	C3B—H3BA	0.9300
N2A—C8A	1.461 (3)	C3C—H3CA	0.9300
N3A—C7A	1.347 (3)	C4A—H4A	0.9300
N3A—H3AB	0.8600	C5A—H5AA	0.9300
N3A—H3AA	0.8600	C5B—H5BA	0.9600
C1A—C2A	1.385 (3)	C5B—H5BB	0.9600
C1A—C6A	1.393 (3)	C5B—H5BC	0.9600
C1B—C2B	1.504 (3)	C5C—H5CA	0.9600
C1C—C2C	1.505 (4)	C5C—H5CB	0.9600
C2A—C3A	1.380 (4)	C5C—H5CC	0.9600
C2B—C3B	1.369 (3)	C8A—H8AA	0.9600
C2C—C3C	1.391 (3)	C8A—H8AB	0.9600
C3A—C4A	1.393 (4)	C8A—H8AC	0.9600
C3B—C4B	1.399 (3)

O1B—V1—O1C	88.57 (6)	C1A—C6A—C5A	123.1 (2)
O1B—V1—O1V	95.11 (7)	N2A—C6A—C1A	105.53 (18)
O1B—V1—O2B	84.14 (6)	N2A—C6A—C5A	131.3 (2)
O1B—V1—O2C	164.96 (7)	N1A—C7A—N2A	112.59 (18)
O1B—V1—N1A	89.89 (6)	N1A—C7A—N3A	125.33 (19)
O1C—V1—O1V	97.22 (7)	N2A—C7A—N3A	122.05 (19)
O1C—V1—O2B	83.09 (6)	C2B—C1B—H1BA	110.00
O1C—V1—O2C	88.62 (6)	C2B—C1B—H1BB	110.00
O1C—V1—N1A	166.93 (7)	C2B—C1B—H1BC	109.00
O1V—V1—O2B	179.18 (7)	H1BA—C1B—H1BB	109.00
O1V—V1—O2C	99.91 (7)	H1BA—C1B—H1BC	109.00
O1V—V1—N1A	95.85 (7)	H1BB—C1B—H1BC	109.00
O2B—V1—O2C	80.85 (6)	C2C—C1C—H1CA	109.00
O2B—V1—N1A	83.84 (6)	C2C—C1C—H1CB	110.00
O2C—V1—N1A	89.52 (6)	C2C—C1C—H1CC	109.00
V1—O1B—C2B	131.18 (13)	H1CA—C1C—H1CB	109.00
V1—O1C—C2C	127.48 (15)	H1CA—C1C—H1CC	109.00
V1—O2B—C4B	129.48 (14)	H1CB—C1C—H1CC	109.00
V1—O2C—C4C	127.37 (13)	C1A—C2A—H2AA	121.00
V1—N1A—C1A	123.89 (12)	C3A—C2A—H2AA	121.00
V1—N1A—C7A	131.02 (14)	C2A—C3A—H3AC	119.00
C1A—N1A—C7A	104.89 (16)	C4A—C3A—H3AC	119.00
C6A—N2A—C7A	107.40 (17)	C2B—C3B—H3BA	117.00
C6A—N2A—C8A	124.86 (19)	C4B—C3B—H3BA	117.00
C7A—N2A—C8A	127.5 (2)	C2C—C3C—H3CA	117.00
H3AA—N3A—H3AB	120.00	C4C—C3C—H3CA	117.00
C7A—N3A—H3AA	120.00	C3A—C4A—H4A	119.00
C7A—N3A—H3AB	120.00	C5A—C4A—H4A	120.00
N1A—C1A—C6A	109.59 (17)	C4A—C5A—H5AA	122.00
N1A—C1A—C2A	130.93 (18)	C6A—C5A—H5AA	122.00
C2A—C1A—C6A	119.5 (2)	C4B—C5B—H5BA	109.00
C1A—C2A—C3A	117.6 (2)	C4B—C5B—H5BB	109.00
O1B—C2B—C1B	115.1 (2)	C4B—C5B—H5BC	109.00
O1B—C2B—C3B	126.17 (19)	H5BA—C5B—H5BB	109.00
C1B—C2B—C3B	118.8 (2)	H5BA—C5B—H5BC	110.00
O1C—C2C—C3C	124.1 (2)	H5BB—C5B—H5BC	109.00
O1C—C2C—C1C	115.5 (2)	C4C—C5C—H5CA	109.00
C1C—C2C—C3C	120.3 (2)	C4C—C5C—H5CB	109.00
C2A—C3A—C4A	122.0 (3)	C4C—C5C—H5CC	109.00
C2B—C3B—C4B	125.4 (2)	H5CA—C5C—H5CB	109.00
C2C—C3C—C4C	125.8 (2)	H5CA—C5C—H5CC	109.00
C3A—C4A—C5A	121.0 (3)	H5CB—C5C—H5CC	109.00
C3B—C4B—C5B	118.5 (2)	N2A—C8A—H8AA	110.00
O2B—C4B—C5B	117.85 (19)	N2A—C8A—H8AB	110.00
O2B—C4B—C3B	123.6 (2)	N2A—C8A—H8AC	110.00
O2C—C4C—C3C	124.9 (2)	H8AA—C8A—H8AB	109.00
O2C—C4C—C5C	115.0 (2)	H8AA—C8A—H8AC	109.00
C3C—C4C—C5C	120.1 (2)	H8AB—C8A—H8AC	109.00
C4A—C5A—C6A	116.9 (2)

O1C—V1—O1B—C2B	−83.35 (17)	V1—N1A—C1A—C2A	−4.2 (3)
O1V—V1—O1B—C2B	179.53 (17)	C1A—N1A—C7A—N3A	−178.0 (2)
O2B—V1—O1B—C2B	−0.15 (17)	V1—N1A—C7A—N3A	7.1 (4)
N1A—V1—O1B—C2B	83.67 (17)	C7A—N1A—C1A—C6A	−0.4 (3)
O1B—V1—O1C—C2C	178.64 (19)	C1A—N1A—C7A—N2A	−0.2 (3)
O1V—V1—O1C—C2C	−86.4 (2)	C7A—N1A—C1A—C2A	−179.6 (3)
O2B—V1—O1C—C2C	94.37 (19)	C8A—N2A—C6A—C5A	−7.5 (5)
O2C—V1—O1C—C2C	13.42 (19)	C8A—N2A—C7A—N1A	−173.6 (2)
O1B—V1—O2B—C4B	0.1 (2)	C7A—N2A—C6A—C5A	177.9 (3)
O1C—V1—O2B—C4B	89.40 (18)	C8A—N2A—C7A—N3A	4.3 (4)
O2C—V1—O2B—C4B	179.11 (19)	C6A—N2A—C7A—N1A	0.8 (3)
N1A—V1—O2B—C4B	−90.39 (18)	C6A—N2A—C7A—N3A	178.6 (2)
O1C—V1—O2C—C4C	−11.2 (2)	C7A—N2A—C6A—C1A	−1.0 (3)
O1V—V1—O2C—C4C	85.9 (2)	C8A—N2A—C6A—C1A	173.6 (2)
O2B—V1—O2C—C4C	−94.4 (2)	N1A—C1A—C2A—C3A	178.8 (3)
N1A—V1—O2C—C4C	−178.3 (2)	N1A—C1A—C6A—C5A	−178.1 (2)
O1B—V1—N1A—C1A	55.10 (17)	N1A—C1A—C6A—N2A	0.8 (3)
O1B—V1—N1A—C7A	−130.9 (2)	C2A—C1A—C6A—N2A	−179.9 (2)
O1V—V1—N1A—C1A	−40.02 (17)	C2A—C1A—C6A—C5A	1.2 (4)
O1V—V1—N1A—C7A	134.0 (2)	C6A—C1A—C2A—C3A	−0.4 (4)
O2B—V1—N1A—C1A	139.22 (17)	C1A—C2A—C3A—C4A	−0.7 (4)
O2B—V1—N1A—C7A	−46.7 (2)	C1B—C2B—C3B—C4B	179.3 (2)
O2C—V1—N1A—C1A	−139.93 (17)	O1B—C2B—C3B—C4B	−0.7 (4)
O2C—V1—N1A—C7A	34.1 (2)	O1C—C2C—C3C—C4C	−2.6 (5)
V1—O1B—C2B—C1B	−179.51 (16)	C1C—C2C—C3C—C4C	176.4 (3)
V1—O1B—C2B—C3B	0.4 (3)	C2A—C3A—C4A—C5A	1.0 (5)
V1—O1C—C2C—C3C	−9.3 (4)	C2B—C3B—C4B—O2B	0.6 (4)
V1—O1C—C2C—C1C	171.7 (2)	C2B—C3B—C4B—C5B	−179.2 (2)
V1—O2B—C4B—C5B	179.41 (15)	C2C—C3C—C4C—C5C	−174.0 (3)
V1—O2B—C4B—C3B	−0.4 (3)	C2C—C3C—C4C—O2C	5.0 (5)
V1—O2C—C4C—C5C	−176.10 (18)	C3A—C4A—C5A—C6A	−0.2 (5)
V1—O2C—C4C—C3C	4.9 (4)	C4A—C5A—C6A—N2A	−179.6 (3)
V1—N1A—C7A—N2A	−175.13 (16)	C4A—C5A—C6A—C1A	−0.9 (4)
V1—N1A—C1A—C6A	174.97 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3AA···O2B	0.86	2.38	2.972 (3)	127
N3A—H3AA···O2C	0.86	2.47	3.034 (2)	124
C8A—H8AA···N3A	0.96	2.61	2.950 (3)	101
C8A—H8AB···O1Cⁱ	0.96	2.57	3.146 (3)	119

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[V(C₅H₇O₂)₂O(C₈H₉N₃)]
M_r	412.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.2712 (1), 15.0472 (2), 16.1078 (2)
β (°)	104.2646 (14)
V (Å³)	1942.94 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.57
Crystal size (mm)	0.25 × 0.12 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.544, 0.694
No. of measured, independent and observed [I > 2σ(I)] reflections	8892, 3720, 2983
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.106, 1.00
No. of reflections	3720
No. of parameters	249
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3AA···O2B	0.86	2.38	2.972 (3)	127
N3A—H3AA···O2C	0.86	2.47	3.034 (2)	124

Acknowledgements

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (No. F 3–142).

References

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