Di-μ-oxido-bis­[(4-formyl-2-methoxy­phenolato-κO1)oxido(1,10-phenan­throline-κ2N,N′)vanadium(V)]

Guo, Z.; Li, L.; Xu, T.; Li, J.

doi:10.1107/S1600536809032516

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1114

doi:10.1107/S1600536809032516

Open

access

Di-μ-oxido-bis[(4-formyl-2-methoxyphenolato-κO¹)oxido(1,10-phenanthroline-κ²N,N′)vanadium(V)]

Zhenghua Guo,^a Lianzhi Li,^a ^* Tao Xu ^a and Jinghong Li ^a

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lilianzhi1963@yahoo.com.cn

(Received 11 August 2009; accepted 16 August 2009; online 22 August 2009)

The title complex, [V₂(C₈H₇O₃)₂O₄(C₁₂H₈N₂)₂], is a centrosymmetric dimer formed by two V^V complex units bridged by two μ₂-oxido groups. The V^V atom is six-coordinated by three oxide O atoms, one O atom from a vanillinate ligand and two N atoms from a 1,10-phenanthroline ligand in a significantly distorted octahedral geometry. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds connect the molecules into a three-dimensional network.

Related literature

For general background to vanadium complexes, see: Dong et al. (2000 ); Thompson et al. (1999 ); Yuan et al. (2003 ). For related structures, see: Li et al. (2004 ); Mokry & Carrano (1993 ).

Experimental

Crystal data

[V₂(C₈H₇O₃)₂O₄(C₁₂H₈N₂)₂]
M_r = 828.56
Triclinic, $[P \overline 1]$
a = 9.3453 (18) Å
b = 9.786 (2) Å
c = 11.090 (3) Å
α = 80.097 (2)°
β = 65.672 (1)°
γ = 71.535 (1)°
V = 875.6 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 298 K
0.21 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.884, T_max = 0.904
4641 measured reflections
3038 independent reflections
2372 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.177
S = 1.07
3038 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O3	1.898 (3)
V1—O4	1.657 (3)
V1—O5	1.610 (3)
V1—O4ⁱ	2.346 (3)
V1—N1	2.148 (3)
V1—N2	2.245 (3)
Symmetry code: (i) -x+2, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱⁱ	0.93	2.48	3.393 (6)	168
C16—H16⋯O4ⁱⁱⁱ	0.93	2.44	3.192 (5)	138
C8—H8A⋯O5^iv	0.96	2.68	3.280 (6)	121
C11—H11⋯O5^v	0.93	2.67	3.312 (5)	127
C1—H1⋯O5^vi	0.93	2.62	3.441 (6)	148
Symmetry codes: (ii) x+1, y-1, z-1; (iii) x-1, y, z; (iv) -x+1, -y+2, -z+2; (v) -x+2, -y+1, -z+1; (vi) -x+2, -y+2, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032516/hy2219sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032516/hy2219Isup2.hkl

checkCIF report

Comment top

There is an increased interest in vanadium complexes due to their possible uses in pharmaceuticals for the treatment of diabetes (Thompson et al., 1999) and their practical applications in catalysis and material science (Yuan et al., 2003). The vanadium complexes with 1,10-phenanthroline ligand have been reported to exhibit potent antitumor activity (Dong et al., 2000). Vanillin is an useful organic compound with multifunctional groups including aldehyde, ether and phenol. In an effort to uncover the chemistry and biochemistry of vanadium with nitrogen- and oxygen-containing ligands, we report herein the synthesis and crystal structure of a new binuclear vanadium(V) complexes with mixed ligands of vanillin and 1,10-phenanthroline.

The molecular structure of the title complex is shown in Fig.1. In the presence of atmosphere, V^IV is oxidized to V^V. The complex is centrosymmetric dimer formed by two V^V complex untis bridged by two µ₂-oxido groups. The V^V atom is six-coordinated by three oxido O atoms, one O atom from a vanillinate ligand and two N atoms from a 1,10-phenanthroline ligand in a significantly distorted octahedral geometry (Table 1). O3, O4, N1 and N2 are situated in the equatorial plane and O5 and O4ⁱ [symmetry code: (i) -x+2, -y+2, -z+1] are in the axial positions. The V^V atom deviates from the least-squares plane of O3, O4, N1 and N2 by 0.319 (1) Å. In the complex, V1—O4 is 1.657 (3) Å and V1—O4ⁱ is 2.346 (3) Å, which illustrates that it is a very asymmetric bridge. The asymmetric structure is similar to that previously reported (Li et al., 2004; Mokry & Carrano, 1993).

There are extensive C—H···O hydrogen bonds in the crystal structure (Table 2). As shown in Fig. 2, the neighboring binuclear complex molecules are connected by the intermolecular hydrogen bonds into a three-dimensional network.

Related literature top

For general background to vanadium complexes, see: Dong et al. (2000); Thompson et al. (1999); Yuan et al. (2003). For related structures, see: Li et al. (2004); Mokry & Carrano (1993).

Experimental top

Vanillin (0.152 g, 1 mmol) was dissolved in 5 ml absolute methanol and vanadyl sulfate hydrate (0.225 g, 1 mmol) was added to the solution, which was stirred and refluxed for 2 h at 323 K. Then, a methanol solution (5 ml) of 1,10-phenanthroline (0.198 g, 1 mmol) was added to the solution. The mixture was stirred and refluxed for 3 h at 323 K. The obtained brown solution was cooled to room temperature and filtered. The filtrate was kept at room temperature for 30 d. The crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. [Symmetry code: (i) -x+2, -y+2, -z+1.]
	Fig. 2. The crystal packing of the title compound with hydrogen bonds (dashed lines).

Di-µ-oxido-bis[(4-formyl-2-methoxyphenolato-κO¹)oxido(1,10- phenanthroline-κ²N,N')vanadium(V)] top

Crystal data top

[V₂(C₈H₇O₃)₂O₄(C₁₂H₈N₂)₂]	Z = 1
M_r = 828.56	F(000) = 424
Triclinic, P1	D_x = 1.571 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3453 (18) Å	Cell parameters from 943 reflections
b = 9.786 (2) Å	θ = 2.5–25.8°
c = 11.090 (3) Å	µ = 0.60 mm⁻¹
α = 80.097 (2)°	T = 298 K
β = 65.672 (1)°	Needle, colorless
γ = 71.535 (1)°	0.21 × 0.18 × 0.17 mm
V = 875.6 (3) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	3038 independent reflections
Radiation source: fine-focus sealed tube	2372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.884, T_max = 0.904	k = −11→8
4641 measured reflections	l = −13→12

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1054P)² + 0.2207P] where P = (F_o² + 2F_c²)/3
3038 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

[V₂(C₈H₇O₃)₂O₄(C₁₂H₈N₂)₂]	γ = 71.535 (1)°
M_r = 828.56	V = 875.6 (3) Å³
Triclinic, P1	Z = 1
a = 9.3453 (18) Å	Mo Kα radiation
b = 9.786 (2) Å	µ = 0.60 mm⁻¹
c = 11.090 (3) Å	T = 298 K
α = 80.097 (2)°	0.21 × 0.18 × 0.17 mm
β = 65.672 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3038 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2372 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.904	R_int = 0.046
4641 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.07	Δρ_max = 0.84 e Å⁻³
3038 reflections	Δρ_min = −0.82 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
V1	0.93548 (8)	0.89398 (7)	0.61983 (7)	0.0324 (3)
N1	1.0193 (4)	0.7386 (3)	0.4733 (3)	0.0337 (7)
N2	0.7109 (4)	0.8658 (3)	0.6109 (3)	0.0329 (7)
O1	0.6378 (5)	1.4243 (4)	1.1968 (4)	0.0683 (10)
O2	0.4949 (4)	1.1848 (4)	0.8894 (3)	0.0544 (9)
O3	0.7773 (3)	1.0430 (3)	0.7319 (3)	0.0385 (7)
O4	1.1051 (3)	0.9466 (3)	0.5544 (3)	0.0340 (6)
O5	0.9616 (4)	0.7689 (3)	0.7300 (3)	0.0439 (7)
C1	0.7557 (7)	1.3424 (6)	1.1248 (5)	0.0544 (12)
H1	0.8544	1.3312	1.1321	0.065*
C2	0.7590 (6)	1.2582 (5)	1.0265 (5)	0.0448 (11)
C3	0.6170 (5)	1.2648 (5)	1.0102 (4)	0.0434 (10)
H3	0.5168	1.3212	1.0643	0.052*
C4	0.6250 (5)	1.1877 (5)	0.9139 (4)	0.0366 (9)
C5	0.7772 (5)	1.1044 (4)	0.8284 (4)	0.0350 (9)
C6	0.9175 (5)	1.0962 (5)	0.8477 (5)	0.0435 (10)
H6	1.0182	1.0399	0.7942	0.052*
C7	0.9070 (6)	1.1723 (5)	0.9469 (5)	0.0465 (11)
H7	1.0011	1.1654	0.9601	0.056*
C8	0.3380 (6)	1.2439 (6)	0.9822 (6)	0.0684 (16)
H8A	0.3289	1.1997	1.0684	0.103*
H8B	0.2582	1.2264	0.9578	0.103*
H8C	0.3195	1.3459	0.9840	0.103*
C9	1.1750 (5)	0.6719 (4)	0.4093 (4)	0.0379 (9)
H9	1.2535	0.6951	0.4269	0.046*
C10	1.2269 (5)	0.5683 (4)	0.3167 (4)	0.0423 (10)
H10	1.3373	0.5232	0.2742	0.051*
C11	1.1117 (6)	0.5345 (4)	0.2897 (4)	0.0448 (11)
H11	1.1438	0.4656	0.2287	0.054*
C12	0.9468 (5)	0.6033 (4)	0.3537 (4)	0.0398 (10)
C13	0.9066 (5)	0.7047 (4)	0.4456 (4)	0.0301 (8)
C14	0.7401 (5)	0.7743 (4)	0.5200 (4)	0.0326 (9)
C15	0.6154 (5)	0.7467 (5)	0.4962 (5)	0.0419 (10)
C16	0.4555 (5)	0.8190 (5)	0.5727 (5)	0.0503 (12)
H16	0.3683	0.8040	0.5616	0.060*
C17	0.4273 (5)	0.9118 (5)	0.6636 (5)	0.0491 (11)
H17	0.3208	0.9608	0.7142	0.059*
C18	0.5583 (5)	0.9333 (5)	0.6811 (4)	0.0407 (10)
H18	0.5375	0.9967	0.7437	0.049*
C19	0.8183 (6)	0.5772 (5)	0.3311 (5)	0.0510 (12)
H19	0.8438	0.5120	0.2686	0.061*
C20	0.6622 (6)	0.6447 (5)	0.3981 (5)	0.0519 (12)
H20	0.5813	0.6254	0.3809	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0238 (4)	0.0321 (4)	0.0453 (4)	−0.0028 (3)	−0.0170 (3)	−0.0116 (3)
N1	0.0333 (18)	0.0263 (17)	0.0485 (19)	−0.0051 (14)	−0.0234 (15)	−0.0047 (14)
N2	0.0259 (17)	0.0315 (18)	0.0425 (19)	−0.0053 (14)	−0.0152 (14)	−0.0043 (14)
O1	0.067 (3)	0.074 (3)	0.067 (2)	−0.010 (2)	−0.023 (2)	−0.037 (2)
O2	0.0297 (16)	0.074 (2)	0.063 (2)	−0.0057 (15)	−0.0158 (15)	−0.0325 (17)
O3	0.0272 (14)	0.0411 (16)	0.0473 (17)	0.0006 (12)	−0.0148 (12)	−0.0200 (13)
O4	0.0232 (13)	0.0363 (15)	0.0449 (15)	−0.0048 (11)	−0.0131 (12)	−0.0143 (12)
O5	0.0441 (17)	0.0433 (17)	0.0491 (17)	−0.0068 (14)	−0.0247 (14)	−0.0059 (14)
C1	0.061 (3)	0.060 (3)	0.050 (3)	−0.020 (3)	−0.025 (3)	−0.009 (2)
C2	0.050 (3)	0.042 (3)	0.050 (3)	−0.012 (2)	−0.025 (2)	−0.007 (2)
C3	0.038 (2)	0.045 (3)	0.044 (2)	−0.0042 (19)	−0.0143 (19)	−0.013 (2)
C4	0.033 (2)	0.040 (2)	0.037 (2)	−0.0078 (18)	−0.0139 (17)	−0.0046 (18)
C5	0.036 (2)	0.035 (2)	0.033 (2)	−0.0100 (18)	−0.0114 (17)	−0.0038 (17)
C6	0.035 (2)	0.041 (2)	0.057 (3)	0.0017 (18)	−0.025 (2)	−0.014 (2)
C7	0.041 (3)	0.051 (3)	0.058 (3)	−0.010 (2)	−0.028 (2)	−0.007 (2)
C8	0.035 (3)	0.086 (4)	0.079 (4)	−0.006 (3)	−0.013 (3)	−0.033 (3)
C9	0.030 (2)	0.032 (2)	0.052 (2)	−0.0033 (17)	−0.0182 (19)	−0.0039 (18)
C10	0.038 (2)	0.031 (2)	0.049 (2)	0.0012 (18)	−0.013 (2)	−0.0095 (19)
C11	0.058 (3)	0.030 (2)	0.045 (2)	−0.007 (2)	−0.019 (2)	−0.0094 (19)
C12	0.048 (3)	0.030 (2)	0.048 (2)	−0.0098 (19)	−0.026 (2)	−0.0034 (18)
C13	0.030 (2)	0.030 (2)	0.033 (2)	−0.0093 (16)	−0.0142 (16)	−0.0009 (16)
C14	0.028 (2)	0.030 (2)	0.044 (2)	−0.0087 (16)	−0.0190 (17)	0.0004 (17)
C15	0.040 (2)	0.038 (2)	0.063 (3)	−0.0146 (19)	−0.034 (2)	0.006 (2)
C16	0.038 (3)	0.052 (3)	0.076 (3)	−0.018 (2)	−0.037 (2)	0.005 (2)
C17	0.027 (2)	0.052 (3)	0.068 (3)	−0.009 (2)	−0.020 (2)	−0.002 (2)
C18	0.027 (2)	0.040 (2)	0.053 (3)	−0.0036 (18)	−0.0163 (19)	−0.004 (2)
C19	0.060 (3)	0.049 (3)	0.064 (3)	−0.016 (2)	−0.037 (3)	−0.014 (2)
C20	0.057 (3)	0.051 (3)	0.071 (3)	−0.020 (2)	−0.043 (3)	−0.002 (2)

Geometric parameters (Å, º) top

V1—O3	1.898 (3)	C7—H7	0.9300
V1—O4	1.657 (3)	C8—H8A	0.9600
V1—O5	1.610 (3)	C8—H8B	0.9600
V1—O4ⁱ	2.346 (3)	C8—H8C	0.9600
V1—N1	2.148 (3)	C9—C10	1.398 (6)
V1—N2	2.245 (3)	C9—H9	0.9300
N1—C9	1.324 (5)	C10—C11	1.372 (6)
N1—C13	1.355 (5)	C10—H10	0.9300
N2—C18	1.319 (5)	C11—C12	1.392 (6)
N2—C14	1.350 (5)	C11—H11	0.9300
O1—C1	1.196 (6)	C12—C13	1.400 (6)
O2—C4	1.359 (5)	C12—C19	1.426 (6)
O2—C8	1.403 (6)	C13—C14	1.425 (6)
O3—C5	1.314 (5)	C14—C15	1.407 (5)
O4—V1ⁱ	2.346 (3)	C15—C16	1.395 (7)
C1—C2	1.459 (6)	C15—C20	1.440 (7)
C1—H1	0.9300	C16—C17	1.362 (7)
C2—C7	1.383 (7)	C16—H16	0.9300
C2—C3	1.393 (6)	C17—C18	1.398 (6)
C3—C4	1.375 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.416 (6)	C19—C20	1.335 (7)
C5—C6	1.390 (6)	C19—H19	0.9300
C6—C7	1.385 (6)	C20—H20	0.9300
C6—H6	0.9300

O5—V1—O4	105.63 (14)	C6—C7—H7	119.4
O5—V1—O3	99.73 (14)	O2—C8—H8A	109.5
O4—V1—O3	105.13 (13)	O2—C8—H8B	109.5
O5—V1—N1	91.67 (14)	H8A—C8—H8B	109.5
O4—V1—N1	93.98 (13)	O2—C8—H8C	109.5
O3—V1—N1	154.01 (13)	H8A—C8—H8C	109.5
O5—V1—N2	99.66 (13)	H8B—C8—H8C	109.5
O4—V1—N2	152.20 (13)	N1—C9—C10	123.1 (4)
O3—V1—N2	81.37 (12)	N1—C9—H9	118.5
N1—V1—N2	73.69 (12)	C10—C9—H9	118.5
O5—V1—O4ⁱ	172.60 (13)	C11—C10—C9	118.7 (4)
O4—V1—O4ⁱ	77.95 (12)	C11—C10—H10	120.6
O3—V1—O4ⁱ	85.35 (11)	C9—C10—H10	120.6
N1—V1—O4ⁱ	81.55 (11)	C10—C11—C12	120.0 (4)
N2—V1—O4ⁱ	75.66 (10)	C10—C11—H11	120.0
C9—N1—C13	117.7 (3)	C12—C11—H11	120.0
C9—N1—V1	123.9 (3)	C11—C12—C13	117.1 (4)
C13—N1—V1	118.3 (3)	C11—C12—C19	124.3 (4)
C18—N2—C14	118.8 (3)	C13—C12—C19	118.6 (4)
C18—N2—V1	126.4 (3)	N1—C13—C12	123.4 (4)
C14—N2—V1	114.8 (2)	N1—C13—C14	116.2 (3)
C4—O2—C8	118.0 (4)	C12—C13—C14	120.4 (3)
C5—O3—V1	132.1 (3)	N2—C14—C15	123.2 (4)
V1—O4—V1ⁱ	102.05 (12)	N2—C14—C13	117.0 (3)
O1—C1—C2	126.1 (5)	C15—C14—C13	119.9 (4)
O1—C1—H1	117.0	C16—C15—C14	116.6 (4)
C2—C1—H1	117.0	C16—C15—C20	125.5 (4)
C7—C2—C3	119.6 (4)	C14—C15—C20	117.9 (4)
C7—C2—C1	119.1 (4)	C17—C16—C15	119.8 (4)
C3—C2—C1	121.3 (4)	C17—C16—H16	120.1
C4—C3—C2	119.9 (4)	C15—C16—H16	120.1
C4—C3—H3	120.1	C16—C17—C18	120.0 (4)
C2—C3—H3	120.1	C16—C17—H17	120.0
O2—C4—C3	125.1 (4)	C18—C17—H17	120.0
O2—C4—C5	114.2 (4)	N2—C18—C17	121.6 (4)
C3—C4—C5	120.7 (4)	N2—C18—H18	119.2
O3—C5—C6	123.8 (4)	C17—C18—H18	119.2
O3—C5—C4	117.4 (4)	C20—C19—C12	121.2 (4)
C6—C5—C4	118.8 (4)	C20—C19—H19	119.4
C7—C6—C5	119.8 (4)	C12—C19—H19	119.4
C7—C6—H6	120.1	C19—C20—C15	121.9 (4)
C5—C6—H6	120.1	C19—C20—H20	119.1
C2—C7—C6	121.2 (4)	C15—C20—H20	119.1
C2—C7—H7	119.4

O5—V1—N1—C9	−77.6 (3)	C3—C4—C5—C6	3.1 (6)
O4—V1—N1—C9	28.2 (3)	O3—C5—C6—C7	175.7 (4)
O3—V1—N1—C9	166.0 (3)	C4—C5—C6—C7	−1.8 (6)
N2—V1—N1—C9	−177.1 (3)	C3—C2—C7—C6	2.3 (7)
O4ⁱ—V1—N1—C9	105.4 (3)	C1—C2—C7—C6	−176.7 (4)
O5—V1—N1—C13	101.4 (3)	C5—C6—C7—C2	−0.9 (7)
O4—V1—N1—C13	−152.8 (3)	C13—N1—C9—C10	−0.7 (6)
O3—V1—N1—C13	−15.1 (5)	V1—N1—C9—C10	178.3 (3)
N2—V1—N1—C13	1.8 (3)	N1—C9—C10—C11	0.5 (6)
O4ⁱ—V1—N1—C13	−75.6 (3)	C9—C10—C11—C12	0.2 (6)
O5—V1—N2—C18	91.8 (3)	C10—C11—C12—C13	−0.7 (6)
O4—V1—N2—C18	−112.8 (4)	C10—C11—C12—C19	179.1 (4)
O3—V1—N2—C18	−6.6 (3)	C9—N1—C13—C12	0.1 (6)
N1—V1—N2—C18	−179.2 (4)	V1—N1—C13—C12	−178.9 (3)
O4ⁱ—V1—N2—C18	−94.0 (3)	C9—N1—C13—C14	177.6 (3)
O5—V1—N2—C14	−90.9 (3)	V1—N1—C13—C14	−1.4 (4)
O4—V1—N2—C14	64.4 (4)	C11—C12—C13—N1	0.5 (6)
O3—V1—N2—C14	170.6 (3)	C19—C12—C13—N1	−179.2 (4)
N1—V1—N2—C14	−2.0 (3)	C11—C12—C13—C14	−176.8 (4)
O4ⁱ—V1—N2—C14	83.2 (3)	C19—C12—C13—C14	3.4 (6)
O5—V1—O3—C5	55.9 (3)	C18—N2—C14—C15	−0.1 (6)
O4—V1—O3—C5	−53.3 (3)	V1—N2—C14—C15	−177.6 (3)
N1—V1—O3—C5	170.7 (3)	C18—N2—C14—C13	179.5 (3)
N2—V1—O3—C5	154.3 (3)	V1—N2—C14—C13	2.0 (4)
O4ⁱ—V1—O3—C5	−129.5 (3)	N1—C13—C14—N2	−0.5 (5)
O5—V1—O4—V1ⁱ	173.33 (13)	C12—C13—C14—N2	177.1 (3)
O3—V1—O4—V1ⁱ	−81.74 (13)	N1—C13—C14—C15	179.1 (3)
N1—V1—O4—V1ⁱ	80.47 (12)	C12—C13—C14—C15	−3.3 (6)
N2—V1—O4—V1ⁱ	18.6 (3)	N2—C14—C15—C16	−0.3 (6)
O4ⁱ—V1—O4—V1ⁱ	0.0	C13—C14—C15—C16	−179.9 (4)
O1—C1—C2—C7	177.4 (5)	N2—C14—C15—C20	−178.9 (4)
O1—C1—C2—C3	−1.6 (8)	C13—C14—C15—C20	1.5 (6)
C7—C2—C3—C4	−1.0 (7)	C14—C15—C16—C17	0.6 (6)
C1—C2—C3—C4	178.0 (4)	C20—C15—C16—C17	179.2 (4)
C8—O2—C4—C3	−11.6 (7)	C15—C16—C17—C18	−0.6 (7)
C8—O2—C4—C5	169.6 (4)	C14—N2—C18—C17	0.2 (6)
C2—C3—C4—O2	179.5 (4)	V1—N2—C18—C17	177.3 (3)
C2—C3—C4—C5	−1.7 (6)	C16—C17—C18—N2	0.2 (7)
V1—O3—C5—C6	17.7 (6)	C11—C12—C19—C20	178.5 (4)
V1—O3—C5—C4	−164.7 (3)	C13—C12—C19—C20	−1.7 (7)
O2—C4—C5—O3	4.3 (5)	C12—C19—C20—C15	−0.1 (8)
C3—C4—C5—O3	−174.6 (3)	C16—C15—C20—C19	−178.3 (5)
O2—C4—C5—C6	−178.0 (4)	C14—C15—C20—C19	0.2 (7)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱⁱ	0.93	2.48	3.393 (6)	168
C16—H16···O4ⁱⁱⁱ	0.93	2.44	3.192 (5)	138
C8—H8A···O5^iv	0.96	2.68	3.280 (6)	121
C11—H11···O5^v	0.93	2.67	3.312 (5)	127
C1—H1···O5^vi	0.93	2.62	3.441 (6)	148

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

Experimental details

Crystal data
Chemical formula	[V₂(C₈H₇O₃)₂O₄(C₁₂H₈N₂)₂]
M_r	828.56
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.3453 (18), 9.786 (2), 11.090 (3)
α, β, γ (°)	80.097 (2), 65.672 (1), 71.535 (1)
V (Å³)	875.6 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.21 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.884, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	4641, 3038, 2372
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.177, 1.07
No. of reflections	3038
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.82

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

V1—O3	1.898 (3)	V1—O4ⁱ	2.346 (3)
V1—O4	1.657 (3)	V1—N1	2.148 (3)
V1—O5	1.610 (3)	V1—N2	2.245 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱⁱ	0.93	2.48	3.393 (6)	168
C16—H16···O4ⁱⁱⁱ	0.93	2.44	3.192 (5)	138
C8—H8A···O5^iv	0.96	2.68	3.280 (6)	121
C11—H11···O5^v	0.93	2.67	3.312 (5)	127
C1—H1···O5^vi	0.93	2.62	3.441 (6)	148

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

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dong, Y. H., Narla, R. K., Sudbeck, E. & Uckun, F. M. (2000). J. Inorg. Biochem. 78, 321–330. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, L. Z., Xu, T., Wang, D. Q. & Ji, H. W. (2004). Chin. J. Inorg. Chem. 20, 236–240. Google Scholar
Mokry, L. M. & Carrano, C. J. (1993). Inorg. Chem. 32, 6119–6121. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thompson, K. H., McNeill, J. H. & Orvig, C. (1999). Chem. Rev. 99, 2561–2571. Web of Science CrossRef PubMed CAS Google Scholar
Yuan, M., Wang, E., Lu, Y., Wang, S., Li, Y., Wang, L. & Hu, C. (2003). Inorg. Chim. Acta, 344, 257–261. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.