(2,2′-Bipyridine)(pyridine-2,6-dicarboxyl­ato)oxidovanadium(IV) ethanol monosolvate

Aghabozorg, H.; Tavakoli, E.; Mirzaei, M.

doi:10.1107/S1600536811002376

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m248-m249

doi:10.1107/S1600536811002376

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(2,2′-Bipyridine)(pyridine-2,6-dicarboxylato)oxidovanadium(IV) ethanol monosolvate

Hossein Aghabozorg,^a ^* Elnaz Tavakoli ^a and Masoud Mirzaei ^b ^*

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com, mirzaei487@yahoo.com

(Received 8 January 2011; accepted 17 January 2011; online 22 January 2011)

In the title compound, [V(C₇H₃NO₄)O(C₁₀H₈N₂)]·C₂H₅OH, the V^IV atom exhibits a distorted octahedral coordination environment formed by two pyridyl N atoms of 2,2′-bipyridine (bpy), the vanadyl O atom, and two carboxylate O atoms and one pyridyl N atom of the tridentate pyridine-2,6-dicarboxylate (pydc²⁻) ligand. The pyridyl N atom of the pydc²⁻ anion and one pyridyl N atom of bpy occupy the axial positions. O—H⋯O hydrogen bonds involving the ethanol solvent molecule as donor and a carboxylate O atom as acceptor atoms, as well as C—H⋯O hydrogen bonds, together with π–π stacking interactions between adjacent aromatic rings (average centroid–centroid distance = 3.577 Å), seem to be effective in the stabilization of the crystal packing, resulting in the formation of a three-dimensional structure.

Related literature

For general background to proton-transfer compounds and their complexes, see: Aghabozorg et al. (2008 ). For related structures with V^IV, see: Therrien et al. (2002 ); Okabe & Muranishi (2002 ).

Experimental

Crystal data

[V(C₇H₃NO₄)O(C₁₀H₈N₂)]·C₂H₆O
M_r = 434.30
Monoclinic, C 2/c
a = 23.246 (2) Å
b = 11.2179 (10) Å
c = 13.9440 (16) Å
β = 97.247 (9)°
V = 3607.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.27 × 0.23 × 0.02 mm

Data collection

Stoe IPDS II Image Plate diffractometer
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009 ) T_min = 0.864, T_max = 1.000
7321 measured reflections
2959 independent reflections
2124 reflections with I > 2I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.144
S = 1.03
2959 reflections
263 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O5	1.586 (3)
V1—N3	2.020 (3)
V1—O1	2.021 (3)
V1—O2	2.035 (3)
V1—N1	2.130 (3)
V1—N2	2.304 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O4ⁱ	0.82	2.00	2.815 (6)	173
C1—H1⋯O6ⁱⁱ	0.93	2.50	3.216 (7)	134
C4—H4⋯O1ⁱⁱⁱ	0.93	2.47	3.207 (6)	137
C9—H9⋯O6^iv	0.93	2.50	3.220 (9)	135
C12—H12⋯O5^v	0.93	2.46	3.374 (5)	166
C14—H14⋯O5^vi	0.93	2.52	3.146 (6)	125
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002376/wm2448sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002376/wm2448Isup2.hkl

checkCIF report

Comment top

2,2'-Bipyridine (bipy) is a bidentate chelating ligand, forming complexes with many transition metals. Ruthenium and platinum complexes of bipy exhibit intense luminescence, which may have practical applications. In continuation of previous works containing V^IVcomplexes and various basic ligands (Aghabozorg et al., 2008; Therrien et al., 2002; Okabe & Muranishi, 2002), we report preparation and the crystal structure of the title compound, [VO(C₁₀H₈N₂)(C₇H₃NO₄)]^.C₂H₅OH, (I).

In the structure of compound (I) the V^IV atom has a distorted octahedral coordination environment formed by two pyridyl N atoms of 2,2'-bipyridine (C₁₀H₈N₂ or bpy), one O atom of the vanadyl group, and two carboxylate O atoms and one pyridyl N atom of the tridentate pyridine-2,6-dicarboxylate (C₇H₃NO₄ or pydc^2-) ligand. The pyridyl N3 atom of pydc^2- and the pyridyl N1 atom of bpy occupy the axial position (Fig. 1). In the crystalline network of (I), O—H···O hydrogen bonds involving the ethanol solvent and C—H···O hydrogen bonds, together with π—π stacking interactions between adjacent aromatic rings [average centroid-to-centroid distance 3.577 Å], seem to be effective in the stabilization of the crystal packing, resulting in the formation of a three-dimensional structure. In this network, layers of pydc^2- and bpy are alternatingly repeated in the bc plane (Fig. 2).

Related literature top

For general background to proton-transfer compounds and their complexes, see: Aghabozorg et al. (2008). For related structures with V^IV, see: Therrien et al. (2002); Okabe & Muranishi (2002).

Experimental top

The reaction of vanadium^III chloride (78 mg, 0.5 mmol), bpy (156 mg, 1 mmol) and pydcH₂ (167 mg, 1 mmol) in a 1:2:2 molar ratio in ethanolic/aqueous solution resulted in the formation of green platy [VO(bpy)(pydc)]^.C₂H₅OH crystals.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The packing diagram of the title compound. The intermolecular classical O—H···O and non-classical C—H···O hydrogen bonds are shown as dashed lines.

(2,2'-Bipyridine)(pyridine-2,6-dicarboxylato)oxidovanadium(IV) ethanol monosolvate top

Crystal data top

[V(C₇H₃NO₄)O(C₁₀H₈N₂)]·C₂H₆O	F(000) = 1784
M_r = 434.30	D_x = 1.599 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2000 reflections
a = 23.246 (2) Å	θ = 1.7–29.6°
b = 11.2179 (10) Å	µ = 0.60 mm⁻¹
c = 13.9440 (16) Å	T = 296 K
β = 97.247 (9)°	Plate, green
V = 3607.1 (6) Å³	0.27 × 0.23 × 0.02 mm
Z = 8

Data collection top

Stoe IPDS II Image Plate diffractometer	2959 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.063
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −27→27
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	k = −13→11
T_min = 0.864, T_max = 1.000	l = −16→16
7321 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0798P)²] where P = (F_o² + 2F_c²)/3
2959 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.40 e Å⁻³
18 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[V(C₇H₃NO₄)O(C₁₀H₈N₂)]·C₂H₆O	V = 3607.1 (6) Å³
M_r = 434.30	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.246 (2) Å	µ = 0.60 mm⁻¹
b = 11.2179 (10) Å	T = 296 K
c = 13.9440 (16) Å	0.27 × 0.23 × 0.02 mm
β = 97.247 (9)°

Data collection top

Stoe IPDS II Image Plate diffractometer	2959 independent reflections
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	2124 reflections with I > 2˘I)
T_min = 0.864, T_max = 1.000	R_int = 0.063
7321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	18 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
2959 reflections	Δρ_min = −0.47 e Å⁻³
263 parameters

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
V1	0.62729 (3)	0.30154 (6)	0.11171 (5)	0.0319 (2)
O1	0.64617 (13)	0.2637 (3)	0.2539 (2)	0.0460 (8)
O2	0.62335 (12)	0.2534 (3)	−0.0297 (2)	0.0407 (7)
O3	0.70520 (19)	0.1657 (4)	0.3648 (2)	0.0789 (13)
O4	0.67163 (17)	0.1626 (4)	−0.1379 (2)	0.0663 (11)
O5	0.66057 (13)	0.4245 (3)	0.1080 (2)	0.0495 (9)
N1	0.54682 (14)	0.3905 (3)	0.1173 (2)	0.0336 (8)
N2	0.55688 (14)	0.1580 (3)	0.1169 (3)	0.0365 (9)
N3	0.68851 (13)	0.1735 (3)	0.1134 (2)	0.0324 (8)
C1	0.5446 (2)	0.5111 (4)	0.1194 (3)	0.0441 (11)
H1	0.5787	0.5543	0.1183	0.053*
C2	0.4937 (2)	0.5712 (5)	0.1233 (4)	0.0531 (13)
H2	0.4937	0.6540	0.1251	0.064*
C3	0.4433 (2)	0.5103 (5)	0.1243 (4)	0.0588 (14)
H3	0.4085	0.5507	0.1264	0.071*
C4	0.44461 (19)	0.3875 (5)	0.1222 (4)	0.0518 (13)
H4	0.4106	0.3440	0.1228	0.062*
C5	0.49684 (16)	0.3294 (4)	0.1192 (3)	0.0353 (10)
C6	0.50287 (17)	0.1984 (4)	0.1193 (3)	0.0356 (10)
C7	0.45626 (19)	0.1219 (4)	0.1245 (3)	0.0479 (12)
H7	0.4191	0.1520	0.1257	0.057*
C8	0.4662 (2)	0.0011 (5)	0.1280 (4)	0.0551 (14)
H8	0.4356	−0.0515	0.1317	0.066*
C9	0.5213 (2)	−0.0420 (5)	0.1261 (4)	0.0559 (14)
H9	0.5286	−0.1235	0.1283	0.067*
C10	0.5657 (2)	0.0393 (4)	0.1206 (4)	0.0474 (12)
H10	0.6031	0.0106	0.1195	0.057*
C11	0.71366 (17)	0.1325 (4)	0.1987 (3)	0.0374 (10)
C12	0.7551 (2)	0.0444 (5)	0.2017 (4)	0.0528 (13)
H12	0.7731	0.0158	0.2606	0.063*
C13	0.7693 (2)	−0.0006 (5)	0.1154 (4)	0.0547 (13)
H13	0.7973	−0.0600	0.1161	0.066*
C14	0.74242 (18)	0.0421 (4)	0.0280 (4)	0.0456 (11)
H14	0.7519	0.0122	−0.0302	0.055*
C15	0.70108 (16)	0.1302 (4)	0.0292 (3)	0.0331 (10)
C16	0.6882 (2)	0.1901 (5)	0.2804 (3)	0.0477 (12)
C17	0.66328 (19)	0.1852 (4)	−0.0549 (3)	0.0418 (11)
C18	0.1764 (7)	0.2303 (15)	0.0306 (11)	0.223 (7)
H18D	0.2105	0.2775	0.0274	0.334*
H18B	0.1481	0.2487	−0.0236	0.334*
H18C	0.1863	0.1473	0.0290	0.334*
C19	0.1528 (6)	0.2564 (11)	0.1197 (11)	0.165 (5)
H19C	0.1874	0.2380	0.1635	0.199*
H19B	0.1537	0.3426	0.1145	0.199*
O6	0.1146 (3)	0.2505 (6)	0.1859 (5)	0.117 (2)
H6	0.1310	0.2704	0.2390	0.175*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0293 (3)	0.0323 (4)	0.0341 (4)	−0.0005 (3)	0.0042 (3)	−0.0012 (3)
O1	0.0457 (16)	0.058 (2)	0.0345 (17)	0.0043 (15)	0.0067 (14)	−0.0067 (15)
O2	0.0434 (16)	0.0462 (18)	0.0318 (16)	0.0035 (14)	0.0016 (13)	0.0045 (14)
O3	0.103 (3)	0.100 (3)	0.0302 (18)	0.021 (3)	−0.005 (2)	0.004 (2)
O4	0.086 (3)	0.083 (3)	0.0307 (18)	0.014 (2)	0.0110 (18)	0.0029 (18)
O5	0.0442 (16)	0.041 (2)	0.066 (2)	−0.0103 (14)	0.0161 (16)	−0.0047 (16)
N1	0.0356 (17)	0.036 (2)	0.0289 (18)	0.0011 (15)	0.0032 (15)	0.0021 (16)
N2	0.0412 (19)	0.033 (2)	0.036 (2)	−0.0059 (15)	0.0083 (16)	−0.0016 (16)
N3	0.0299 (15)	0.034 (2)	0.0332 (19)	−0.0005 (14)	0.0027 (15)	−0.0007 (16)
C1	0.055 (3)	0.040 (3)	0.038 (3)	0.001 (2)	0.008 (2)	0.001 (2)
C2	0.069 (3)	0.041 (3)	0.050 (3)	0.020 (2)	0.013 (3)	0.006 (2)
C3	0.056 (3)	0.064 (4)	0.060 (3)	0.028 (3)	0.024 (3)	0.025 (3)
C4	0.038 (2)	0.067 (4)	0.053 (3)	0.006 (2)	0.014 (2)	0.024 (3)
C5	0.035 (2)	0.045 (3)	0.026 (2)	0.0034 (18)	0.0040 (18)	0.0083 (19)
C6	0.040 (2)	0.043 (3)	0.025 (2)	−0.006 (2)	0.0081 (17)	0.003 (2)
C7	0.043 (2)	0.054 (3)	0.047 (3)	−0.014 (2)	0.007 (2)	0.001 (2)
C8	0.060 (3)	0.060 (4)	0.046 (3)	−0.032 (3)	0.011 (2)	−0.004 (3)
C9	0.075 (3)	0.036 (3)	0.056 (3)	−0.020 (2)	0.008 (3)	0.000 (2)
C10	0.051 (2)	0.039 (3)	0.053 (3)	−0.003 (2)	0.008 (2)	0.000 (2)
C11	0.037 (2)	0.045 (3)	0.030 (2)	−0.0020 (19)	0.0022 (18)	0.002 (2)
C12	0.051 (3)	0.057 (3)	0.048 (3)	0.014 (2)	−0.003 (2)	0.008 (3)
C13	0.046 (2)	0.053 (3)	0.066 (4)	0.018 (2)	0.011 (2)	0.006 (3)
C14	0.049 (2)	0.043 (3)	0.049 (3)	0.000 (2)	0.024 (2)	−0.006 (2)
C15	0.0354 (19)	0.036 (3)	0.029 (2)	−0.0064 (18)	0.0116 (17)	−0.0022 (19)
C16	0.051 (2)	0.055 (3)	0.036 (2)	−0.001 (2)	0.001 (2)	−0.001 (2)
C17	0.046 (2)	0.046 (3)	0.034 (2)	−0.005 (2)	0.008 (2)	0.005 (2)
C18	0.265 (17)	0.258 (19)	0.143 (13)	−0.065 (15)	0.017 (13)	−0.007 (12)
C19	0.201 (13)	0.137 (10)	0.160 (13)	0.007 (10)	0.031 (11)	−0.016 (10)
O6	0.092 (3)	0.137 (5)	0.116 (5)	−0.009 (3)	−0.002 (3)	−0.045 (4)

Geometric parameters (Å, º) top

V1—O5	1.586 (3)	C6—C7	1.391 (6)
V1—N3	2.020 (3)	C7—C8	1.375 (7)
V1—O1	2.021 (3)	C7—H7	0.9300
V1—O2	2.035 (3)	C8—C9	1.372 (8)
V1—N1	2.130 (3)	C8—H8	0.9300
V1—N2	2.304 (3)	C9—C10	1.386 (7)
O1—C16	1.297 (5)	C9—H9	0.9300
O2—C17	1.286 (6)	C10—H10	0.9300
O3—C16	1.225 (5)	C11—C12	1.376 (6)
O4—C17	1.224 (6)	C11—C16	1.495 (7)
N1—C5	1.353 (5)	C12—C13	1.384 (7)
N1—C1	1.354 (5)	C12—H12	0.9300
N2—C6	1.339 (5)	C13—C14	1.383 (7)
N2—C10	1.347 (6)	C13—H13	0.9300
N3—C15	1.336 (5)	C14—C15	1.380 (6)
N3—C11	1.339 (5)	C14—H14	0.9300
C1—C2	1.369 (7)	C15—C17	1.506 (6)
C1—H1	0.9300	C18—C19	1.451 (19)
C2—C3	1.359 (7)	C18—H18D	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C3—C4	1.377 (7)	C18—H18C	0.9600
C3—H3	0.9300	C19—O6	1.359 (15)
C4—C5	1.384 (6)	C19—H19C	0.9700
C4—H4	0.9300	C19—H19B	0.9700
C5—C6	1.475 (6)	O6—H6	0.8200

O5—V1—N3	105.83 (15)	C8—C7—H7	120.6
O5—V1—O1	99.69 (15)	C6—C7—H7	120.6
N3—V1—O1	76.93 (13)	C9—C8—C7	119.9 (5)
O5—V1—O2	99.30 (16)	C9—C8—H8	120.0
N3—V1—O2	76.59 (12)	C7—C8—H8	120.0
O1—V1—O2	150.73 (13)	C8—C9—C10	118.2 (5)
O5—V1—N1	91.59 (15)	C8—C9—H9	120.9
N3—V1—N1	162.44 (14)	C10—C9—H9	120.9
O1—V1—N1	98.38 (13)	N2—C10—C9	122.8 (5)
O2—V1—N1	103.14 (12)	N2—C10—H10	118.6
O5—V1—N2	163.88 (15)	C9—C10—H10	118.6
N3—V1—N2	90.28 (13)	N3—C11—C12	120.0 (4)
O1—V1—N2	83.65 (13)	N3—C11—C16	111.0 (4)
O2—V1—N2	84.25 (13)	C12—C11—C16	129.0 (4)
N1—V1—N2	72.30 (13)	C11—C12—C13	118.6 (4)
C16—O1—V1	118.4 (3)	C11—C12—H12	120.7
C17—O2—V1	118.5 (3)	C13—C12—H12	120.7
C5—N1—C1	118.1 (4)	C14—C13—C12	120.6 (4)
C5—N1—V1	121.6 (3)	C14—C13—H13	119.7
C1—N1—V1	120.3 (3)	C12—C13—H13	119.7
C6—N2—C10	118.1 (4)	C15—C14—C13	118.3 (4)
C6—N2—V1	115.8 (3)	C15—C14—H14	120.8
C10—N2—V1	126.0 (3)	C13—C14—H14	120.8
C15—N3—C11	122.4 (4)	N3—C15—C14	120.1 (4)
C15—N3—V1	118.7 (3)	N3—C15—C17	111.4 (4)
C11—N3—V1	118.9 (3)	C14—C15—C17	128.5 (4)
N1—C1—C2	121.9 (5)	O3—C16—O1	123.8 (5)
N1—C1—H1	119.1	O3—C16—C11	121.6 (4)
C2—C1—H1	119.1	O1—C16—C11	114.5 (4)
C3—C2—C1	120.3 (5)	O4—C17—O2	126.0 (4)
C3—C2—H2	119.8	O4—C17—C15	120.3 (4)
C1—C2—H2	119.8	O2—C17—C15	113.6 (4)
C2—C3—C4	118.7 (4)	C19—C18—H18D	109.5
C2—C3—H3	120.7	C19—C18—H18B	109.5
C4—C3—H3	120.7	H18D—C18—H18B	109.5
C3—C4—C5	119.6 (5)	C19—C18—H18C	109.5
C3—C4—H4	120.2	H18D—C18—H18C	109.5
C5—C4—H4	120.2	H18B—C18—H18C	109.5
N1—C5—C4	121.4 (4)	O6—C19—C18	157.2 (13)
N1—C5—C6	115.0 (4)	O6—C19—H19C	97.0
C4—C5—C6	123.6 (4)	C18—C19—H19C	97.0
N2—C6—C7	122.1 (4)	O6—C19—H19B	97.0
N2—C6—C5	115.2 (4)	C18—C19—H19B	97.0
C7—C6—C5	122.7 (4)	H19C—C19—H19B	103.5
C8—C7—C6	118.8 (5)	C19—O6—H6	109.5

O5—V1—O1—C16	−98.6 (3)	V1—N1—C5—C4	−179.6 (3)
N3—V1—O1—C16	5.5 (3)	C1—N1—C5—C6	−178.4 (4)
O2—V1—O1—C16	31.2 (5)	V1—N1—C5—C6	1.3 (5)
N1—V1—O1—C16	168.3 (3)	C3—C4—C5—N1	−0.7 (7)
N2—V1—O1—C16	97.3 (3)	C3—C4—C5—C6	178.4 (4)
O5—V1—O2—C17	93.9 (3)	C10—N2—C6—C7	−0.6 (6)
N3—V1—O2—C17	−10.3 (3)	V1—N2—C6—C7	−178.7 (3)
O1—V1—O2—C17	−35.9 (5)	C10—N2—C6—C5	177.5 (4)
N1—V1—O2—C17	−172.2 (3)	V1—N2—C6—C5	−0.6 (5)
N2—V1—O2—C17	−101.9 (3)	N1—C5—C6—N2	−0.3 (5)
O5—V1—N1—C5	178.2 (3)	C4—C5—C6—N2	−179.5 (4)
N3—V1—N1—C5	−8.7 (6)	N1—C5—C6—C7	177.7 (4)
O1—V1—N1—C5	−81.7 (3)	C4—C5—C6—C7	−1.4 (7)
O2—V1—N1—C5	78.3 (3)	N2—C6—C7—C8	0.4 (7)
N2—V1—N1—C5	−1.2 (3)	C5—C6—C7—C8	−177.5 (4)
O5—V1—N1—C1	−2.1 (3)	C6—C7—C8—C9	−0.2 (8)
N3—V1—N1—C1	171.0 (4)	C7—C8—C9—C10	0.1 (8)
O1—V1—N1—C1	98.0 (3)	C6—N2—C10—C9	0.5 (7)
O2—V1—N1—C1	−102.0 (3)	V1—N2—C10—C9	178.4 (4)
N2—V1—N1—C1	178.5 (3)	C8—C9—C10—N2	−0.2 (8)
O5—V1—N2—C6	−1.2 (7)	C15—N3—C11—C12	1.5 (6)
N3—V1—N2—C6	178.7 (3)	V1—N3—C11—C12	179.3 (3)
O1—V1—N2—C6	101.8 (3)	C15—N3—C11—C16	−175.6 (4)
O2—V1—N2—C6	−104.9 (3)	V1—N3—C11—C16	2.2 (5)
N1—V1—N2—C6	0.9 (3)	N3—C11—C12—C13	−0.6 (7)
O5—V1—N2—C10	−179.1 (5)	C16—C11—C12—C13	175.9 (5)
N3—V1—N2—C10	0.7 (4)	C11—C12—C13—C14	−0.1 (8)
O1—V1—N2—C10	−76.1 (4)	C12—C13—C14—C15	−0.1 (7)
O2—V1—N2—C10	77.2 (4)	C11—N3—C15—C14	−1.7 (6)
N1—V1—N2—C10	−177.0 (4)	V1—N3—C15—C14	−179.5 (3)
O5—V1—N3—C15	−89.6 (3)	C11—N3—C15—C17	175.4 (4)
O1—V1—N3—C15	173.8 (3)	V1—N3—C15—C17	−2.4 (4)
O2—V1—N3—C15	6.4 (3)	C13—C14—C15—N3	1.0 (6)
N1—V1—N3—C15	97.6 (5)	C13—C14—C15—C17	−175.6 (4)
N2—V1—N3—C15	90.4 (3)	V1—O1—C16—O3	176.1 (4)
O5—V1—N3—C11	92.5 (3)	V1—O1—C16—C11	−6.0 (5)
O1—V1—N3—C11	−4.1 (3)	N3—C11—C16—O3	−179.7 (5)
O2—V1—N3—C11	−171.5 (3)	C12—C11—C16—O3	3.6 (8)
N1—V1—N3—C11	−80.3 (5)	N3—C11—C16—O1	2.4 (6)
N2—V1—N3—C11	−87.5 (3)	C12—C11—C16—O1	−174.4 (5)
C5—N1—C1—C2	−0.1 (6)	V1—O2—C17—O4	−168.8 (4)
V1—N1—C1—C2	−179.8 (4)	V1—O2—C17—C15	11.9 (5)
N1—C1—C2—C3	−0.5 (8)	N3—C15—C17—O4	174.6 (4)
C1—C2—C3—C4	0.5 (8)	C14—C15—C17—O4	−8.6 (7)
C2—C3—C4—C5	0.1 (8)	N3—C15—C17—O2	−6.1 (5)
C1—N1—C5—C4	0.7 (6)	C14—C15—C17—O2	170.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4ⁱ	0.82	2.00	2.815 (6)	173
C1—H1···O6ⁱⁱ	0.93	2.50	3.216 (7)	134
C4—H4···O1ⁱⁱⁱ	0.93	2.47	3.207 (6)	137
C9—H9···O6^iv	0.93	2.50	3.220 (9)	135
C12—H12···O5^v	0.93	2.46	3.374 (5)	166
C14—H14···O5^vi	0.93	2.52	3.146 (6)	125

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

Experimental details

Crystal data
Chemical formula	[V(C₇H₃NO₄)O(C₁₀H₈N₂)]·C₂H₆O
M_r	434.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.246 (2), 11.2179 (10), 13.9440 (16)
β (°)	97.247 (9)
V (Å³)	3607.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.27 × 0.23 × 0.02

Data collection
Diffractometer	Stoe IPDS II Image Plate diffractometer
Absorption correction	Multi-scan (MULABS in PLATON; Spek, 2009)
T_min, T_max	0.864, 1.000
No. of measured, independent and observed [I > 2˘I)] reflections	7321, 2959, 2124
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.144, 1.03
No. of reflections	2959
No. of parameters	263
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.47

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

V1—O5	1.586 (3)	V1—O2	2.035 (3)
V1—N3	2.020 (3)	V1—N1	2.130 (3)
V1—O1	2.021 (3)	V1—N2	2.304 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4ⁱ	0.82	2.00	2.815 (6)	173
C1—H1···O6ⁱⁱ	0.93	2.50	3.216 (7)	134
C4—H4···O1ⁱⁱⁱ	0.93	2.47	3.207 (6)	137
C9—H9···O6^iv	0.93	2.50	3.220 (9)	135
C12—H12···O5^v	0.93	2.46	3.374 (5)	166
C14—H14···O5^vi	0.93	2.52	3.146 (6)	125

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

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Okabe, N. & Muranishi, Y. (2002). Acta Cryst. E58, m287–m289. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Therrien, B., Stanislas, S., Stoeckli-Evans, H., Shul'pin, G. B. & Süss-Fink, G. (2002). Acta Cryst. E58, m215–m216. Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m248-m249

doi:10.1107/S1600536811002376

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2,2′-Bi­pyridine)(pyridine-2,6-di­carboxyl­ato)oxidovanadium(IV) ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(2,2′-Bipyridine)(pyridine-2,6-dicarboxylato)oxidovanadium(IV) ethanol monosolvate