Oxido[N-(2-oxidobenzyl-idene-κO)leucinato-κ²N,O](1,10-phenanthroline-κ²N,N')vanadium(IV).

In the title V(IV) complex, [VO(C₁₃H₁₅NO₃)(C₁₂H₈N₂)], the oxidovanadium cation is N,N'-chelated by a 1-10-phenanthroline ligand and N,O,O'-chelated by a Schiff base anion in a distorted octa-hedral geometry. Weak inter-molecular C-H⋯O hydrogen bonds occur in the crystal structure which contains solvent-accessible voids of 81 ų.

Related literature

For the biological and pharmacological properties of vanadium complexes, see: Baran (2003 ▶). For the structures of similar six-coordinate oxidovanadium complexes with amino acid Schiff base ligands, see: Bian et al. (2011 ▶); Cao et al. (2011 ▶); Xu et al. (2005 ▶); Li et al. (2006 ▶, 2010 ▶); Lu et al. (2011 ▶); Sasmal et al. (2007 ▶).

Experimental

Crystal data

[V(C13H15NO3)O(C12H8N2)]

M = 480.40

Hexagonal,

a = 33.675 (4) Å

c = 10.283 (2) Å

V = 10099 (3) Å3

Z = 18

Mo Kα radiation

μ = 0.48 mm−1

T = 298 K

0.23 × 0.11 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.898, T max = 0.963

17437 measured reflections

3962 independent reflections

2020 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.128

S = 1.00

3962 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025391/xu5555sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025391/xu5555Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[V(C13H15NO3)O(C12H8N2)]	Dx = 1.422 Mg m−3
Mr = 480.40	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 3014 reflections
Hall symbol: -R 3	θ = 2.4–28.3°
a = 33.675 (4) Å	µ = 0.48 mm−1
c = 10.283 (2) Å	T = 298 K
V = 10099 (3) Å3	Block, yellow
Z = 18	0.23 × 0.11 × 0.08 mm
F(000) = 4482

Bruker SMART 1000 CCD area-detector diffractometer	3962 independent reflections
Radiation source: fine-focus sealed tube	2020 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.137
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −35→40
Tmin = 0.898, Tmax = 0.963	k = −39→39
17437 measured reflections	l = −12→11

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3
3962 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
V1	0.88840 (2)	0.14374 (2)	0.82377 (7)	0.0405 (3)
N1	0.93728 (11)	0.12709 (11)	0.7777 (3)	0.0400 (9)
N2	0.85177 (11)	0.17154 (11)	0.9193 (3)	0.0364 (9)
N3	0.93599 (11)	0.19076 (10)	0.9904 (3)	0.0344 (9)
O1	0.87689 (9)	0.09726 (9)	0.9600 (3)	0.0488 (8)
O2	0.89395 (11)	0.04585 (11)	1.0382 (3)	0.0667 (10)
O3	0.92356 (10)	0.20089 (9)	0.7295 (3)	0.0486 (8)
O4	0.84766 (10)	0.11361 (10)	0.7265 (3)	0.0594 (9)
C1	0.89801 (15)	0.07417 (16)	0.9562 (5)	0.0482 (13)
C2	0.92849 (15)	0.08310 (14)	0.8356 (5)	0.0493 (13)
H2	0.9575	0.0850	0.8605	0.059*
C3	0.90355 (16)	0.04533 (15)	0.7341 (5)	0.0632 (15)
H3A	0.8758	0.0454	0.7096	0.076*
H3B	0.9228	0.0536	0.6574	0.076*
C4	0.89048 (18)	−0.00300 (17)	0.7707 (6)	0.0700 (16)
H4	0.8709	−0.0112	0.8479	0.084*
C5	0.9313 (2)	−0.00798 (19)	0.8060 (7)	0.121 (3)
H5A	0.9210	−0.0390	0.8318	0.181*
H5B	0.9477	0.0123	0.8766	0.181*
H5C	0.9512	−0.0004	0.7321	0.181*
C6	0.8627 (2)	−0.03564 (18)	0.6648 (6)	0.109 (2)
H6A	0.8541	−0.0663	0.6903	0.164*
H6B	0.8805	−0.0279	0.5865	0.164*
H6C	0.8356	−0.0337	0.6498	0.164*
C7	0.97293 (15)	0.14987 (16)	0.7061 (4)	0.0469 (12)
H7	0.9921	0.1377	0.6939	0.056*
C8	0.98550 (14)	0.19273 (15)	0.6433 (4)	0.0399 (11)
C9	0.96116 (15)	0.21653 (15)	0.6601 (4)	0.0415 (11)
C10	0.97886 (17)	0.25974 (16)	0.6011 (5)	0.0570 (14)
H10	0.9639	0.2763	0.6133	0.068*
C11	1.01764 (19)	0.27800 (19)	0.5261 (5)	0.0657 (15)
H11	1.0288	0.3068	0.4888	0.079*
C12	1.04026 (17)	0.2539 (2)	0.5057 (5)	0.0657 (16)
H12	1.0659	0.2659	0.4522	0.079*
C13	1.02484 (15)	0.21226 (18)	0.5642 (5)	0.0563 (14)
H13	1.0407	0.1965	0.5515	0.068*
C14	0.80925 (14)	0.16091 (14)	0.8869 (4)	0.0444 (12)
H14	0.7952	0.1409	0.8177	0.053*
C15	0.78503 (15)	0.17820 (16)	0.9513 (5)	0.0534 (14)
H15	0.7554	0.1698	0.9257	0.064*
C16	0.80519 (17)	0.20759 (17)	1.0524 (5)	0.0536 (14)
H16	0.7890	0.2187	1.0980	0.064*
C17	0.85043 (16)	0.22109 (15)	1.0881 (4)	0.0421 (12)
C18	0.87224 (13)	0.20153 (13)	1.0202 (4)	0.0332 (10)
C19	0.91747 (13)	0.21233 (13)	1.0547 (4)	0.0329 (10)
C20	0.94042 (15)	0.24385 (14)	1.1550 (4)	0.0409 (11)
C21	0.98392 (16)	0.25152 (15)	1.1888 (5)	0.0515 (13)
H21	1.0003	0.2719	1.2554	0.062*
C22	1.00214 (15)	0.22934 (16)	1.1246 (5)	0.0491 (13)
H22	1.0310	0.2342	1.1464	0.059*
C23	0.97694 (15)	0.19928 (14)	1.0259 (4)	0.0430 (12)
H23	0.9898	0.1842	0.9822	0.052*
C24	0.87448 (19)	0.25339 (16)	1.1893 (5)	0.0551 (14)
H24	0.8602	0.2667	1.2346	0.066*
C25	0.91796 (18)	0.26461 (16)	1.2196 (4)	0.0565 (14)
H25	0.9335	0.2864	1.2839	0.068*

	U11	U22	U33	U12	U13	U23
V1	0.0317 (5)	0.0396 (5)	0.0497 (5)	0.0173 (4)	−0.0018 (4)	−0.0068 (4)
N1	0.030 (2)	0.037 (2)	0.053 (3)	0.0164 (19)	0.0006 (19)	−0.0056 (19)
N2	0.029 (2)	0.036 (2)	0.045 (2)	0.0169 (18)	0.0024 (18)	0.0046 (19)
N3	0.027 (2)	0.033 (2)	0.045 (2)	0.0173 (18)	−0.0001 (18)	−0.0003 (17)
O1	0.0430 (19)	0.0417 (19)	0.062 (2)	0.0215 (17)	0.0091 (16)	0.0017 (16)
O2	0.070 (2)	0.064 (2)	0.068 (3)	0.035 (2)	0.0031 (19)	0.017 (2)
O3	0.047 (2)	0.0468 (19)	0.059 (2)	0.0287 (17)	0.0139 (17)	0.0082 (16)
O4	0.048 (2)	0.059 (2)	0.071 (2)	0.0265 (17)	−0.0164 (17)	−0.0237 (18)
C1	0.037 (3)	0.039 (3)	0.057 (4)	0.011 (3)	−0.005 (3)	−0.007 (3)
C2	0.036 (3)	0.035 (3)	0.077 (4)	0.018 (2)	−0.001 (3)	−0.002 (3)
C3	0.067 (4)	0.044 (3)	0.083 (4)	0.030 (3)	0.001 (3)	−0.005 (3)
C4	0.065 (4)	0.046 (3)	0.103 (5)	0.030 (3)	0.000 (3)	−0.005 (3)
C5	0.085 (5)	0.068 (4)	0.221 (8)	0.047 (4)	−0.010 (5)	0.009 (5)
C6	0.131 (6)	0.050 (4)	0.136 (6)	0.038 (4)	−0.034 (5)	−0.031 (4)
C7	0.041 (3)	0.051 (3)	0.059 (3)	0.031 (3)	−0.001 (3)	−0.013 (3)
C8	0.035 (3)	0.040 (3)	0.043 (3)	0.018 (2)	0.003 (2)	−0.001 (2)
C9	0.038 (3)	0.040 (3)	0.037 (3)	0.013 (3)	−0.010 (2)	−0.010 (2)
C10	0.070 (4)	0.048 (3)	0.052 (3)	0.028 (3)	−0.001 (3)	−0.001 (3)
C11	0.075 (4)	0.066 (4)	0.039 (3)	0.022 (4)	0.001 (3)	0.010 (3)
C12	0.046 (3)	0.086 (4)	0.043 (4)	0.017 (3)	0.001 (3)	0.006 (3)
C13	0.037 (3)	0.071 (4)	0.055 (3)	0.023 (3)	0.001 (3)	−0.007 (3)
C14	0.026 (3)	0.040 (3)	0.063 (3)	0.013 (2)	−0.005 (2)	0.001 (2)
C15	0.031 (3)	0.058 (3)	0.082 (4)	0.030 (3)	0.005 (3)	0.014 (3)
C16	0.054 (4)	0.063 (4)	0.061 (4)	0.042 (3)	0.023 (3)	0.022 (3)
C17	0.046 (3)	0.044 (3)	0.047 (3)	0.031 (3)	0.014 (3)	0.012 (2)
C18	0.033 (3)	0.029 (2)	0.038 (3)	0.015 (2)	0.007 (2)	0.010 (2)
C19	0.031 (3)	0.028 (2)	0.037 (3)	0.012 (2)	0.008 (2)	0.008 (2)
C20	0.046 (3)	0.039 (3)	0.035 (3)	0.019 (3)	0.006 (2)	0.002 (2)
C21	0.051 (3)	0.047 (3)	0.047 (3)	0.017 (3)	−0.009 (3)	−0.007 (2)
C22	0.029 (3)	0.057 (3)	0.059 (3)	0.020 (3)	−0.006 (3)	−0.001 (3)
C23	0.037 (3)	0.040 (3)	0.049 (3)	0.018 (2)	0.002 (2)	0.001 (3)
C24	0.071 (4)	0.047 (3)	0.057 (4)	0.036 (3)	0.023 (3)	0.005 (3)
C25	0.066 (4)	0.052 (3)	0.049 (3)	0.028 (3)	0.005 (3)	−0.010 (3)

V1—O1	1.989 (3)	C7—H7	0.9300
V1—O3	1.941 (3)	C8—C13	1.407 (6)
V1—O4	1.587 (3)	C8—C9	1.414 (6)
V1—N1	2.042 (3)	C9—C10	1.405 (6)
V1—N2	2.125 (3)	C10—C11	1.369 (6)
V1—N3	2.340 (3)	C10—H10	0.9300
N1—C7	1.285 (5)	C11—C12	1.379 (6)
N1—C2	1.483 (5)	C11—H11	0.9300
N2—C14	1.333 (5)	C12—C13	1.367 (6)
N2—C18	1.369 (5)	C12—H12	0.9300
N3—C23	1.312 (5)	C13—H13	0.9300
N3—C19	1.344 (5)	C14—C15	1.385 (6)
O1—C1	1.290 (5)	C14—H14	0.9300
O2—C1	1.228 (5)	C15—C16	1.360 (6)
O3—C9	1.313 (5)	C15—H15	0.9300
C1—C2	1.541 (6)	C16—C17	1.403 (6)
C2—C3	1.531 (6)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.394 (5)
C3—C4	1.506 (6)	C17—C24	1.429 (6)
C3—H3A	0.9700	C18—C19	1.423 (5)
C3—H3B	0.9700	C19—C20	1.403 (5)
C4—C6	1.497 (7)	C20—C21	1.398 (6)
C4—C5	1.511 (6)	C20—C25	1.425 (6)
C4—H4	0.9800	C21—C22	1.352 (6)
C5—H5A	0.9600	C21—H21	0.9300
C5—H5B	0.9600	C22—C23	1.384 (6)
C5—H5C	0.9600	C22—H22	0.9300
C6—H6A	0.9600	C23—H23	0.9300
C6—H6B	0.9600	C24—C25	1.353 (6)
C6—H6C	0.9600	C24—H24	0.9300
C7—C8	1.438 (6)	C25—H25	0.9300
O4—V1—O3	102.90 (15)	H6B—C6—H6C	109.5
O4—V1—O1	100.04 (14)	N1—C7—C8	125.1 (4)
O3—V1—O1	156.11 (12)	N1—C7—H7	117.5
O4—V1—N1	103.66 (14)	C8—C7—H7	117.5
O3—V1—N1	88.88 (13)	C13—C8—C9	118.9 (4)
O1—V1—N1	79.28 (13)	C13—C8—C7	117.7 (4)
O4—V1—N2	93.81 (14)	C9—C8—C7	123.4 (4)
O3—V1—N2	89.71 (12)	O3—C9—C10	118.4 (4)
O1—V1—N2	95.35 (12)	O3—C9—C8	123.7 (4)
N1—V1—N2	162.35 (14)	C10—C9—C8	118.0 (4)
O4—V1—N3	167.06 (14)	C11—C10—C9	121.6 (5)
O3—V1—N3	79.80 (12)	C11—C10—H10	119.2
O1—V1—N3	79.32 (11)	C9—C10—H10	119.2
N1—V1—N3	88.98 (12)	C10—C11—C12	120.3 (5)
N2—V1—N3	73.46 (13)	C10—C11—H11	119.8
C7—N1—C2	119.1 (4)	C12—C11—H11	119.8
C7—N1—V1	127.6 (3)	C13—C12—C11	119.9 (5)
C2—N1—V1	113.3 (3)	C13—C12—H12	120.1
C14—N2—C18	117.7 (4)	C11—C12—H12	120.1
C14—N2—V1	123.2 (3)	C12—C13—C8	121.3 (5)
C18—N2—V1	119.1 (3)	C12—C13—H13	119.3
C23—N3—C19	117.8 (4)	C8—C13—H13	119.3
C23—N3—V1	129.9 (3)	N2—C14—C15	123.2 (4)
C19—N3—V1	112.3 (3)	N2—C14—H14	118.4
C1—O1—V1	120.3 (3)	C15—C14—H14	118.4
C9—O3—V1	131.1 (3)	C16—C15—C14	119.1 (4)
O2—C1—O1	124.5 (5)	C16—C15—H15	120.4
O2—C1—C2	120.6 (5)	C14—C15—H15	120.4
O1—C1—C2	114.9 (4)	C15—C16—C17	120.1 (4)
N1—C2—C3	108.0 (4)	C15—C16—H16	119.9
N1—C2—C1	107.4 (4)	C17—C16—H16	119.9
C3—C2—C1	110.6 (4)	C18—C17—C16	117.3 (4)
N1—C2—H2	110.3	C18—C17—C24	119.5 (4)
C3—C2—H2	110.3	C16—C17—C24	123.2 (5)
C1—C2—H2	110.3	N2—C18—C17	122.5 (4)
C4—C3—C2	118.1 (4)	N2—C18—C19	117.2 (4)
C4—C3—H3A	107.8	C17—C18—C19	120.2 (4)
C2—C3—H3A	107.8	N3—C19—C20	122.8 (4)
C4—C3—H3B	107.8	N3—C19—C18	117.8 (4)
C2—C3—H3B	107.8	C20—C19—C18	119.4 (4)
H3A—C3—H3B	107.1	C21—C20—C19	116.9 (4)
C6—C4—C3	110.4 (5)	C21—C20—C25	123.9 (4)
C6—C4—C5	111.3 (5)	C19—C20—C25	119.1 (4)
C3—C4—C5	112.9 (4)	C22—C21—C20	120.0 (4)
C6—C4—H4	107.3	C22—C21—H21	120.0
C3—C4—H4	107.3	C20—C21—H21	120.0
C5—C4—H4	107.3	C21—C22—C23	118.7 (4)
C4—C5—H5A	109.5	C21—C22—H22	120.6
C4—C5—H5B	109.5	C23—C22—H22	120.6
H5A—C5—H5B	109.5	N3—C23—C22	123.8 (4)
C4—C5—H5C	109.5	N3—C23—H23	118.1
H5A—C5—H5C	109.5	C22—C23—H23	118.1
H5B—C5—H5C	109.5	C25—C24—C17	120.2 (4)
C4—C6—H6A	109.5	C25—C24—H24	119.9
C4—C6—H6B	109.5	C17—C24—H24	119.9
H6A—C6—H6B	109.5	C24—C25—C20	121.5 (4)
C4—C6—H6C	109.5	C24—C25—H25	119.3
H6A—C6—H6C	109.5	C20—C25—H25	119.3
C1—C2—C3—C4	−62.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O4i	0.93	2.44	3.311 (6)	156
C24—H24···O1ii	0.93	2.51	3.224 (6)	134

Table 1

Selected bond lengths (Å)

V1—O1	1.989 (3)
V1—O3	1.941 (3)
V1—O4	1.587 (3)
V1—N1	2.042 (3)
V1—N2	2.125 (3)
V1—N3	2.340 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O4i	0.93	2.44	3.311 (6)	156
C24—H24⋯O1ii	0.93	2.51	3.224 (6)	134

Symmetry codes: (i) ; (ii) .