(Methanol-κO)(methano­lato-κO)oxido[N-(2-oxidobenzyl­idene)phenyl­alaninato-κ3O,N,O′]vanadium(V)

Bian, L.; Li, L.

doi:10.1107/S1600536811003163

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m274

doi:10.1107/S1600536811003163

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(Methanol-κO)(methanolato-κO)oxido[N-(2-oxidobenzylidene)phenylalaninato-κ³O,N,O′]vanadium(V)

Lin Bian ^a and Lianzhi 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 17 January 2011; accepted 24 January 2011; online 29 January 2011)

In the title complex, [V(C₁₆H₁₃NO₃)(CH₃O)O(CH₃OH)], the V^V atom is six-coordinated by a tridentate ligand derived from the condensation of salicylaldehyde and L-phenylalanine, a vanadyl O atom, a methanolate O atom and a methanol O atom, forming a distorted octahedral coordination geometry. In the crystal, intermolecular O—H⋯O and C—H⋯O hydrogen bonds result in a two-dimensional structure parallel to (001).

Related literature

For general background to the coordination chemistry of vanadium, see: Diego et al. (2003 ); Kenji et al. (2000 ); Thompson et al. (1999 ); Thompson & Orvig (2006 ); Wikksky et al. (2001 ).

Experimental

Crystal data

[V(C₁₆H₁₃NO₃)(CH₃O)O(CH₄O)]
M_r = 397.29
Orthorhombic, P 2₁ 2₁ 2
a = 14.3095 (15) Å
b = 18.782 (2) Å
c = 6.6986 (7) Å
V = 1800.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 298 K
0.45 × 0.42 × 0.41 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.779, T_max = 0.795
8134 measured reflections
3177 independent reflections
2293 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.129
S = 1.03
3177 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ), 1328 Friedel pairs
Flack parameter: 0.04 (4)

Table 1
Selected bond lengths (Å)

V1—O1	1.570 (3)
V1—O2	1.934 (3)
V1—O4	1.831 (3)
V1—O5	2.366 (3)
V1—O6	1.762 (3)
V1—N1	2.086 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H19⋯O3ⁱ	1.00 (5)	1.73 (5)	2.687 (4)	161 (4)
C13—H13⋯O3ⁱⁱ	0.93	2.59	3.500 (7)	165
Symmetry codes: (i) -x+2, -y+2, z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z]$ .

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) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003163/hy2401sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003163/hy2401Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of vanadium has been receiving increasing interest since it was found that vanadium compounds in various oxidation states have insulin-mimetic properties (Diego et al., 2003; Kenji et al., 2000; Thompson & Orvig, 2006). Compared with other transition metal complexes, less vanadium complexes have been synthesized and characterized (Thompson et al., 1999; Wikksky et al., 2001). We report here the synthesis and crystal structure of an oxovanadium(V) complex with a tetradentate Schiff-base ligand derived from the condensation of salicylaldehyde and L-phenylalanine.

As shown in Fig. 1, the V^V ion is six-coordinated by the tridentate (O,N,O) donor ligand and three O atoms from an oxido group, a methanolate group and a methanol molecule (Table 1), forming a distorted octahedral geometry. In the complex, O2, N1 and O4 of the tridentate Schiff base ligand and O6 of the methanolate ligand define the equatorial plane and the oxido O1 and the methanol O5 occupy the axial positions. The Schiff base ligand coordinating to the V^V atom forms two chelating rings, the five-membered V1—O2—C1—C2—N1 ring and the six-membered V1—N1—C10—C11—C16—O4 ring. The dihedral angle of the two rings is 15.69 (15)°, which increases the stability of the complex.

In the crystal, the intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) result in a two-dimensional structure (Fig. 2).

Related literature top

For general background to the coordination chemistry of vanadium, see: Diego et al. (2003); Kenji et al. (2000); Thompson et al. (1999); Thompson & Orvig (2006); Wikksky et al. (2001).

Experimental top

L-Phenylalanine (1 mmol, 0.165 g) and potassium hydroxide (1 mmol, 0.056 g) were dissolved in hot methanol (10 ml) with stirring. The mixture was added successively to a methanol solution (5 ml) of salicylaldehyde (1 mmol, 0.11 ml) with stirring at 323 K for 2 h. Subsequently, an aqueous solution (2 ml) of vanadyl sulfate hydrate (1 mmol, 0.225 g) was added dropwise and stirred for 3 h continuously. The resultant solution was filtered and the filtrate was held at room temperature for several days, whereupon red blocky 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) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The two-dimensional structure of the title compound, linked by intermolecular hydrogen bonds (dashed lines).

(Methanol-κO)(methanolato-κO)oxido[N-(2- oxidobenzylidene)phenylalaninato- κ³O,N,O']vanadium(V) top

Crystal data top

[V(C₁₆H₁₃NO₃)(CH₃O)O(CH₄O)]	F(000) = 824
M_r = 397.29	D_x = 1.466 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2512 reflections
a = 14.3095 (15) Å	θ = 2.6–23.6°
b = 18.782 (2) Å	µ = 0.59 mm⁻¹
c = 6.6986 (7) Å	T = 298 K
V = 1800.3 (3) Å³	Block, red
Z = 4	0.45 × 0.42 × 0.41 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3177 independent reflections
Radiation source: fine-focus sealed tube	2293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→17
T_min = 0.779, T_max = 0.795	k = −22→12
8134 measured reflections	l = −7→7

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0594P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3177 reflections	Δρ_max = 0.46 e Å⁻³
241 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1328 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Crystal data top

[V(C₁₆H₁₃NO₃)(CH₃O)O(CH₄O)]	V = 1800.3 (3) Å³
M_r = 397.29	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 14.3095 (15) Å	µ = 0.59 mm⁻¹
b = 18.782 (2) Å	T = 298 K
c = 6.6986 (7) Å	0.45 × 0.42 × 0.41 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3177 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2293 reflections with I > 2σ(I)
T_min = 0.779, T_max = 0.795	R_int = 0.073
8134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	Δρ_max = 0.46 e Å⁻³
S = 1.03	Δρ_min = −0.48 e Å⁻³
3177 reflections	Absolute structure: Flack (1983), 1328 Friedel pairs
241 parameters	Absolute structure parameter: 0.04 (4)
0 restraints

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

	x	y	z	U_iso*/U_eq
V1	0.84142 (5)	0.86795 (4)	0.57437 (11)	0.0419 (3)
O1	0.7400 (2)	0.8810 (2)	0.6561 (5)	0.0676 (12)
O2	0.8790 (2)	0.96385 (16)	0.5061 (5)	0.0482 (9)
O3	0.8863 (2)	1.05118 (18)	0.2846 (6)	0.0613 (10)
O4	0.8383 (2)	0.77184 (17)	0.5287 (5)	0.0535 (9)
O5	0.9878 (2)	0.85346 (17)	0.4151 (5)	0.0465 (8)
O6	0.9045 (2)	0.8721 (2)	0.7999 (4)	0.0549 (9)
N1	0.7976 (2)	0.87816 (19)	0.2787 (5)	0.0323 (9)
C1	0.8574 (3)	0.9935 (3)	0.3387 (8)	0.0425 (12)
C2	0.7896 (3)	0.9517 (2)	0.2140 (7)	0.0369 (11)
H2	0.8048	0.9560	0.0719	0.044*
C3	0.6910 (3)	0.9796 (2)	0.2553 (8)	0.0480 (13)
H3A	0.6811	0.9811	0.3985	0.058*
H3B	0.6864	1.0280	0.2057	0.058*
C4	0.6158 (3)	0.9364 (2)	0.1631 (7)	0.0405 (12)
C5	0.5940 (4)	0.9426 (3)	−0.0351 (8)	0.0579 (15)
H5	0.6261	0.9753	−0.1138	0.069*
C6	0.5261 (4)	0.9017 (4)	−0.1182 (10)	0.081 (2)
H6	0.5114	0.9076	−0.2524	0.097*
C7	0.4796 (4)	0.8527 (4)	−0.0100 (13)	0.082 (2)
H7	0.4332	0.8248	−0.0679	0.099*
C8	0.5020 (4)	0.8451 (3)	0.1849 (12)	0.0731 (19)
H8	0.4712	0.8109	0.2609	0.088*
C9	0.5687 (4)	0.8864 (3)	0.2722 (9)	0.0613 (16)
H9	0.5823	0.8805	0.4069	0.074*
C10	0.7750 (3)	0.8287 (2)	0.1591 (7)	0.0338 (10)
H10	0.7585	0.8417	0.0298	0.041*
C11	0.7727 (3)	0.7552 (2)	0.2063 (7)	0.0363 (11)
C12	0.7375 (3)	0.7080 (3)	0.0650 (9)	0.0502 (12)
H12	0.7199	0.7248	−0.0600	0.060*
C13	0.7286 (3)	0.6378 (3)	0.1077 (9)	0.0607 (15)
H13	0.7044	0.6068	0.0124	0.073*
C14	0.7550 (4)	0.6124 (3)	0.2902 (10)	0.0632 (16)
H14	0.7480	0.5643	0.3190	0.076*
C15	0.7917 (4)	0.6572 (3)	0.4311 (10)	0.0575 (14)
H15	0.8104	0.6391	0.5540	0.069*
C16	0.8010 (3)	0.7291 (3)	0.3918 (7)	0.0436 (12)
C17	1.0399 (4)	0.7920 (3)	0.3821 (11)	0.078 (2)
H17A	1.0050	0.7513	0.4264	0.117*
H17B	1.0975	0.7948	0.4551	0.117*
H17C	1.0530	0.7874	0.2422	0.117*
C18	0.9966 (5)	0.8865 (4)	0.8526 (10)	0.096 (2)
H18A	1.0209	0.9233	0.7677	0.143*
H18B	1.0334	0.8441	0.8372	0.143*
H18C	0.9989	0.9019	0.9891	0.143*
H19	1.024 (4)	0.896 (3)	0.376 (8)	0.065 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0372 (4)	0.0665 (5)	0.0222 (4)	−0.0044 (4)	−0.0019 (4)	−0.0005 (4)
O1	0.042 (2)	0.132 (4)	0.0290 (18)	−0.001 (2)	0.0042 (16)	−0.004 (2)
O2	0.050 (2)	0.057 (2)	0.038 (2)	0.0011 (17)	−0.0172 (16)	−0.0117 (15)
O3	0.068 (2)	0.048 (2)	0.068 (3)	−0.0181 (19)	−0.021 (2)	0.0047 (19)
O4	0.060 (2)	0.062 (2)	0.039 (2)	−0.0178 (18)	−0.0140 (19)	0.0158 (16)
O5	0.0393 (18)	0.051 (2)	0.050 (2)	−0.0013 (16)	0.0070 (18)	0.0033 (19)
O6	0.050 (2)	0.089 (3)	0.0254 (17)	−0.008 (2)	−0.0088 (16)	−0.0017 (19)
N1	0.0256 (19)	0.041 (2)	0.030 (2)	−0.0024 (17)	0.0054 (15)	−0.0029 (18)
C1	0.035 (3)	0.050 (3)	0.043 (3)	0.005 (2)	−0.011 (2)	−0.004 (2)
C2	0.036 (3)	0.044 (3)	0.031 (3)	−0.006 (2)	−0.005 (2)	−0.001 (2)
C3	0.045 (3)	0.049 (3)	0.049 (3)	0.001 (2)	−0.005 (3)	−0.005 (2)
C4	0.034 (3)	0.046 (3)	0.042 (3)	0.002 (2)	−0.005 (2)	−0.007 (2)
C5	0.036 (3)	0.088 (4)	0.049 (4)	−0.001 (3)	−0.010 (3)	0.003 (3)
C6	0.053 (4)	0.135 (6)	0.055 (4)	0.002 (4)	−0.024 (3)	−0.025 (4)
C7	0.038 (3)	0.088 (5)	0.121 (7)	−0.007 (3)	−0.009 (4)	−0.038 (4)
C8	0.035 (3)	0.093 (5)	0.091 (5)	−0.011 (3)	−0.001 (4)	0.008 (4)
C9	0.041 (3)	0.097 (5)	0.047 (3)	−0.013 (3)	−0.004 (3)	0.007 (3)
C10	0.027 (2)	0.051 (3)	0.023 (2)	0.000 (2)	−0.0017 (19)	−0.003 (2)
C11	0.028 (3)	0.048 (3)	0.032 (3)	0.002 (2)	0.000 (2)	−0.001 (2)
C12	0.045 (3)	0.056 (3)	0.049 (3)	0.002 (2)	−0.006 (3)	−0.012 (3)
C13	0.050 (3)	0.051 (3)	0.081 (5)	−0.005 (3)	0.006 (3)	−0.017 (4)
C14	0.070 (4)	0.042 (3)	0.077 (5)	−0.014 (3)	0.004 (4)	0.004 (3)
C15	0.058 (3)	0.054 (3)	0.061 (4)	−0.008 (3)	0.005 (3)	0.019 (3)
C16	0.037 (3)	0.056 (3)	0.039 (3)	−0.007 (2)	0.002 (2)	0.003 (2)
C17	0.067 (4)	0.063 (4)	0.105 (6)	0.005 (3)	0.032 (4)	−0.003 (4)
C18	0.078 (5)	0.165 (7)	0.044 (4)	−0.014 (4)	−0.032 (4)	0.001 (4)

Geometric parameters (Å, º) top

V1—O1	1.570 (3)	C6—H6	0.9300
V1—O2	1.934 (3)	C7—C8	1.352 (9)
V1—O4	1.831 (3)	C7—H7	0.9300
V1—O5	2.366 (3)	C8—C9	1.361 (8)
V1—O6	1.762 (3)	C8—H8	0.9300
V1—N1	2.086 (4)	C9—H9	0.9300
O2—C1	1.289 (5)	C10—C11	1.417 (6)
O3—C1	1.215 (6)	C10—H10	0.9300
O4—C16	1.331 (5)	C11—C12	1.390 (6)
O5—C17	1.392 (6)	C11—C16	1.395 (6)
O5—H19	1.00 (5)	C12—C13	1.356 (6)
O6—C18	1.390 (6)	C12—H12	0.9300
N1—C10	1.269 (5)	C13—C14	1.365 (8)
N1—C2	1.451 (5)	C13—H13	0.9300
C1—C2	1.503 (6)	C14—C15	1.369 (8)
C2—C3	1.531 (6)	C14—H14	0.9300
C2—H2	0.9800	C15—C16	1.382 (6)
C3—C4	1.483 (6)	C15—H15	0.9300
C3—H3A	0.9700	C17—H17A	0.9600
C3—H3B	0.9700	C17—H17B	0.9600
C4—C9	1.368 (7)	C17—H17C	0.9600
C4—C5	1.369 (7)	C18—H18A	0.9600
C5—C6	1.359 (8)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—C7	1.347 (9)

O1—V1—O6	99.65 (17)	C7—C6—C5	121.3 (7)
O1—V1—O4	100.91 (19)	C7—C6—H6	119.4
O6—V1—O4	101.54 (16)	C5—C6—H6	119.4
O1—V1—O2	101.17 (18)	C6—C7—C8	118.3 (6)
O6—V1—O2	91.07 (15)	C6—C7—H7	120.8
O4—V1—O2	152.27 (15)	C8—C7—H7	120.8
O1—V1—N1	92.22 (16)	C7—C8—C9	121.4 (6)
O6—V1—N1	164.59 (15)	C7—C8—H8	119.3
O4—V1—N1	85.67 (14)	C9—C8—H8	119.3
O2—V1—N1	76.92 (14)	C8—C9—C4	120.5 (6)
O1—V1—O5	173.31 (16)	C8—C9—H9	119.8
O6—V1—O5	86.45 (14)	C4—C9—H9	119.8
O4—V1—O5	80.40 (14)	N1—C10—C11	125.3 (4)
O2—V1—O5	75.80 (13)	N1—C10—H10	117.3
N1—V1—O5	81.31 (12)	C11—C10—H10	117.3
C1—O2—V1	122.7 (3)	C12—C11—C16	119.2 (5)
C16—O4—V1	136.1 (3)	C12—C11—C10	118.5 (4)
C17—O5—V1	129.8 (3)	C16—C11—C10	122.3 (4)
C17—O5—H19	110 (3)	C13—C12—C11	120.7 (5)
V1—O5—H19	119 (3)	C13—C12—H12	119.7
C18—O6—V1	135.4 (3)	C11—C12—H12	119.7
C10—N1—C2	119.2 (4)	C12—C13—C14	120.1 (5)
C10—N1—V1	127.5 (3)	C12—C13—H13	119.9
C2—N1—V1	113.2 (3)	C14—C13—H13	119.9
O3—C1—O2	124.3 (5)	C13—C14—C15	120.7 (5)
O3—C1—C2	121.3 (4)	C13—C14—H14	119.7
O2—C1—C2	114.4 (4)	C15—C14—H14	119.7
N1—C2—C1	106.3 (4)	C14—C15—C16	120.3 (6)
N1—C2—C3	110.2 (4)	C14—C15—H15	119.8
C1—C2—C3	108.4 (4)	C16—C15—H15	119.8
N1—C2—H2	110.6	O4—C16—C15	119.8 (5)
C1—C2—H2	110.6	O4—C16—C11	121.2 (4)
C3—C2—H2	110.6	C15—C16—C11	119.0 (5)
C4—C3—C2	113.9 (4)	O5—C17—H17A	109.5
C4—C3—H3A	108.8	O5—C17—H17B	109.5
C2—C3—H3A	108.8	H17A—C17—H17B	109.5
C4—C3—H3B	108.8	O5—C17—H17C	109.5
C2—C3—H3B	108.8	H17A—C17—H17C	109.5
H3A—C3—H3B	107.7	H17B—C17—H17C	109.5
C9—C4—C5	117.7 (5)	O6—C18—H18A	109.5
C9—C4—C3	120.8 (5)	O6—C18—H18B	109.5
C5—C4—C3	121.5 (5)	H18A—C18—H18B	109.5
C6—C5—C4	120.8 (6)	O6—C18—H18C	109.5
C6—C5—H5	119.6	H18A—C18—H18C	109.5
C4—C5—H5	119.6	H18B—C18—H18C	109.5

O1—V1—O2—C1	−83.7 (4)	V1—N1—C2—C3	−90.1 (4)
O6—V1—O2—C1	176.2 (4)	O3—C1—C2—N1	158.9 (4)
O4—V1—O2—C1	58.5 (5)	O2—C1—C2—N1	−23.0 (5)
N1—V1—O2—C1	6.0 (3)	O3—C1—C2—C3	−82.7 (6)
O5—V1—O2—C1	90.1 (3)	O2—C1—C2—C3	95.4 (5)
O1—V1—O4—C16	75.3 (5)	N1—C2—C3—C4	−56.0 (6)
O6—V1—O4—C16	177.7 (4)	C1—C2—C3—C4	−171.9 (4)
O2—V1—O4—C16	−66.9 (6)	C2—C3—C4—C9	97.9 (6)
N1—V1—O4—C16	−16.1 (4)	C2—C3—C4—C5	−79.1 (6)
O5—V1—O4—C16	−98.0 (5)	C9—C4—C5—C6	1.8 (8)
O6—V1—O5—C17	85.4 (5)	C3—C4—C5—C6	178.9 (5)
O4—V1—O5—C17	−16.9 (5)	C4—C5—C6—C7	−1.5 (9)
O2—V1—O5—C17	177.4 (5)	C5—C6—C7—C8	0.1 (10)
N1—V1—O5—C17	−104.0 (5)	C6—C7—C8—C9	1.1 (10)
O1—V1—O6—C18	−157.1 (6)	C7—C8—C9—C4	−0.8 (9)
O4—V1—O6—C18	99.6 (6)	C5—C4—C9—C8	−0.6 (8)
O2—V1—O6—C18	−55.6 (6)	C3—C4—C9—C8	−177.7 (5)
N1—V1—O6—C18	−17.2 (10)	C2—N1—C10—C11	−175.2 (4)
O5—V1—O6—C18	20.1 (6)	V1—N1—C10—C11	1.8 (6)
O1—V1—N1—C10	−95.5 (4)	N1—C10—C11—C12	173.7 (4)
O6—V1—N1—C10	124.0 (6)	N1—C10—C11—C16	−3.7 (7)
O4—V1—N1—C10	5.3 (3)	C16—C11—C12—C13	1.5 (7)
O2—V1—N1—C10	163.6 (4)	C10—C11—C12—C13	−175.9 (4)
O5—V1—N1—C10	86.2 (4)	C11—C12—C13—C14	−0.6 (8)
O1—V1—N1—C2	81.7 (3)	C12—C13—C14—C15	−0.7 (8)
O6—V1—N1—C2	−58.8 (7)	C13—C14—C15—C16	1.1 (8)
O4—V1—N1—C2	−177.5 (3)	V1—O4—C16—C15	−162.9 (4)
O2—V1—N1—C2	−19.3 (3)	V1—O4—C16—C11	18.6 (7)
O5—V1—N1—C2	−96.6 (3)	C14—C15—C16—O4	−178.8 (5)
V1—O2—C1—O3	−173.7 (4)	C14—C15—C16—C11	−0.2 (8)
V1—O2—C1—C2	8.3 (5)	C12—C11—C16—O4	177.5 (4)
C10—N1—C2—C1	−155.4 (4)	C10—C11—C16—O4	−5.2 (7)
V1—N1—C2—C1	27.2 (4)	C12—C11—C16—C15	−1.1 (7)
C10—N1—C2—C3	87.4 (5)	C10—C11—C16—C15	176.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H19···O3ⁱ	1.00 (5)	1.73 (5)	2.687 (4)	161 (4)
C13—H13···O3ⁱⁱ	0.93	2.59	3.500 (7)	165

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

Experimental details

Crystal data
Chemical formula	[V(C₁₆H₁₃NO₃)(CH₃O)O(CH₄O)]
M_r	397.29
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	298
a, b, c (Å)	14.3095 (15), 18.782 (2), 6.6986 (7)
V (Å³)	1800.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.45 × 0.42 × 0.41

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.779, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	8134, 3177, 2293
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.129, 1.03
No. of reflections	3177
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.48
Absolute structure	Flack (1983), 1328 Friedel pairs
Absolute structure parameter	0.04 (4)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

V1—O1	1.570 (3)	V1—O5	2.366 (3)
V1—O2	1.934 (3)	V1—O6	1.762 (3)
V1—O4	1.831 (3)	V1—N1	2.086 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H19···O3ⁱ	1.00 (5)	1.73 (5)	2.687 (4)	161 (4)
C13—H13···O3ⁱⁱ	0.93	2.59	3.500 (7)	165

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

Acknowledgements

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

References

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