Di-μ-oxido-bis-({(R)-(-)-2-[1-(2-amino-propyl-imino)eth-yl]-1-naphtholato-κN,N',O}oxidovanadium(V)).

In the title dinuclear compound, [V(2)(C(15)H(17)N(2)O)(2)O(4)], each V(V) atom is six-coordinated by one oxide group, and by two N and one O atom of the tridentate Schiff base ligand, and bridged by two additional oxide O atoms, resulting in a centrosymmetric dimer. The metal centre has a distorted octa-hedral coordination with the monoanionic Schiff base ligand occupying one equatorial and two axial coordination positions. The separation between V atoms is 3.214 (3) Å. In the crystal structure, there are N-H⋯O, C-H⋯O and C-H⋯π hydrogen bonds, and π-π inter-actions.

Related literature

For general background, see: Sigel & Sigel (1995 ▶); Butler & Walker (1993 ▶); Martinez et al. (2001 ▶); Rehder (1991 ▶); Thompson & Orvig (2000 ▶); Evangelou (2002 ▶); Kwiatkowski et al. (2003 ▶, 2006 ▶, 2007 ▶); Romanowski et al. (2008 ▶); Rehder (1999 ▶); Colpas et al. (1994 ▶); Li et al. (1988 ▶); Fulwood et al. (1995 ▶). For related structures, see: Root et al. (1993 ▶); Romanowski et al. (2008 ▶); Rayati et al. (2007 ▶, 2008 ▶); Kwiatkowski et al. (2007 ▶). For the synthesis, see: Kwiatkowski et al. (2003 ▶).

Experimental

Crystal data

[V2(C15H17N2O)2O4]

M = 648.49

Monoclinic,

a = 25.187 (5) Å

b = 7.663 (2) Å

c = 16.898 (3) Å

β = 118.09 (3)°

V = 2877.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 298 (2) K

0.28 × 0.13 × 0.12 mm

Data collection

Oxford Diffraction Sapphire CCD diffractometer

Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.828, T max = 0.918

9202 measured reflections

2474 independent reflections

2086 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.153

S = 1.23

2474 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801787X/xu2429sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801787X/xu2429Isup2.hkl

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

[V2(C15H17N2O)2O4]	F000 = 1344
Mr = 648.49	Dx = 1.497 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2875 reflections
a = 25.187 (5) Å	θ = 2.8–25.0º
b = 7.663 (2) Å	µ = 0.70 mm−1
c = 16.898 (3) Å	T = 298 (2) K
β = 118.09 (3)º	Needle, yellow
V = 2877.3 (13) Å3	0.28 × 0.13 × 0.12 mm
Z = 4

Oxford Diffraction Sapphire CCD diffractometer	2474 independent reflections
Radiation source: fine-focus sealed tube	2086 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.078
T = 298(2) K	θmax = 25.0º
θ/2θ scans	θmin = 2.8º
Absorption correction: numerical(CrysAlis RED; Oxford Diffraction, 2006)	h = −25→29
Tmin = 0.828, Tmax = 0.918	k = −9→8
9202 measured reflections	l = −20→20

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)] = 0.084	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0144P)2 + 24.507P] where P = (Fo2 + 2Fc2)/3
S = 1.23	(Δ/σ)max = 0.001
2474 reflections	Δρmax = 0.66 e Å−3
202 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
V1	0.22582 (5)	0.07588 (12)	0.02520 (6)	0.0261 (3)
O1	0.1947 (2)	−0.1142 (5)	0.0042 (3)	0.0419 (11)
N1	0.3137 (2)	−0.0142 (6)	0.0585 (3)	0.0323 (12)
H1A	0.3102	−0.1053	0.0226	0.039*
H1B	0.3330	0.0713	0.0457	0.039*
O2	0.28370 (18)	0.3407 (5)	0.0711 (2)	0.0308 (9)
C3	0.3353 (3)	0.0368 (9)	0.2130 (4)	0.0413 (16)
H3A	0.3546	0.1468	0.2393	0.050*
H3B	0.3476	−0.0479	0.2612	0.050*
N4	0.2701 (2)	0.0595 (6)	0.1714 (3)	0.0266 (10)
C5	0.2442 (3)	0.0737 (7)	0.2207 (4)	0.0307 (13)
C6	0.1780 (3)	0.0906 (7)	0.1799 (4)	0.0301 (13)
C7	0.1481 (3)	0.0356 (7)	0.2291 (4)	0.0361 (15)
H7A	0.1702	−0.0160	0.2850	0.043*
C8	0.0877 (3)	0.0571 (9)	0.1958 (4)	0.0413 (16)
H8A	0.0691	0.0174	0.2287	0.050*
C9	0.0529 (3)	0.1389 (8)	0.1121 (4)	0.0384 (15)
C10	−0.0103 (3)	0.1660 (9)	0.0753 (5)	0.0475 (18)
H10A	−0.0300	0.1282	0.1069	0.057*
C11	−0.0422 (3)	0.2461 (10)	−0.0052 (6)	0.056 (2)
H11A	−0.0834	0.2628	−0.0275	0.068*
C12	−0.0147 (3)	0.3033 (10)	−0.0545 (5)	0.056 (2)
H12A	−0.0370	0.3601	−0.1089	0.067*
C13	0.0463 (3)	0.2751 (8)	−0.0219 (4)	0.0415 (16)
H13A	0.0646	0.3107	−0.0558	0.050*
C14	0.0811 (3)	0.1941 (7)	0.0611 (4)	0.0315 (13)
C15	0.1446 (2)	0.1620 (7)	0.0945 (4)	0.0264 (12)
O16	0.16869 (17)	0.2114 (5)	0.0436 (2)	0.0288 (9)
C18	0.2780 (3)	0.0802 (9)	0.3211 (4)	0.0414 (15)
H18A	0.3139	0.1484	0.3397	0.062*
H18B	0.2887	−0.0361	0.3444	0.062*
H18C	0.2531	0.1324	0.3436	0.062*
C2A	0.3524 (5)	−0.070 (2)	0.1537 (8)	0.042 (4)	0.54 (2)
H2A	0.3435	−0.1922	0.1590	0.051*	0.54 (2)
C17A	0.419 (2)	−0.055 (6)	0.180 (3)	0.067 (15)	0.54 (2)
H17A	0.4422	−0.1162	0.2359	0.101*	0.54 (2)
H17B	0.4306	0.0653	0.1877	0.101*	0.54 (2)
H17C	0.4262	−0.1063	0.1344	0.101*	0.54 (2)
C2B	0.3583 (6)	0.041 (3)	0.1485 (9)	0.029 (4)*	0.46 (2)
H2B	0.3679	0.1637	0.1437	0.034*	0.46 (2)
C17B	0.418 (3)	−0.071 (6)	0.184 (4)	0.046 (11)*	0.46 (2)
H17D	0.4385	−0.0718	0.2485	0.069*	0.46 (2)
H17E	0.4442	−0.0207	0.1630	0.069*	0.46 (2)
H17F	0.4084	−0.1885	0.1622	0.069*	0.46 (2)

	U11	U22	U33	U12	U13	U23
V1	0.0346 (5)	0.0226 (5)	0.0201 (5)	0.0047 (5)	0.0121 (4)	0.0020 (4)
O1	0.052 (3)	0.026 (2)	0.049 (3)	0.000 (2)	0.024 (2)	0.0016 (19)
N1	0.044 (3)	0.024 (3)	0.034 (3)	0.004 (2)	0.022 (3)	0.002 (2)
O2	0.042 (2)	0.028 (2)	0.023 (2)	0.0073 (18)	0.0157 (19)	0.0015 (17)
C3	0.035 (4)	0.052 (4)	0.029 (3)	0.014 (3)	0.008 (3)	0.009 (3)
N4	0.032 (3)	0.025 (3)	0.023 (2)	0.007 (2)	0.013 (2)	0.010 (2)
C5	0.045 (3)	0.022 (3)	0.025 (3)	−0.003 (3)	0.017 (3)	0.003 (3)
C6	0.043 (3)	0.021 (3)	0.032 (3)	−0.001 (3)	0.022 (3)	0.002 (3)
C7	0.053 (4)	0.026 (3)	0.036 (3)	−0.001 (3)	0.027 (3)	0.001 (3)
C8	0.054 (4)	0.040 (4)	0.042 (4)	−0.008 (3)	0.033 (3)	−0.001 (3)
C9	0.039 (4)	0.032 (3)	0.047 (4)	−0.008 (3)	0.023 (3)	−0.008 (3)
C10	0.037 (4)	0.043 (4)	0.069 (5)	−0.003 (3)	0.030 (4)	−0.001 (4)
C11	0.028 (4)	0.052 (5)	0.074 (6)	0.001 (3)	0.012 (4)	−0.006 (4)
C12	0.042 (4)	0.047 (5)	0.063 (5)	0.008 (4)	0.012 (4)	0.014 (4)
C13	0.041 (4)	0.034 (3)	0.041 (4)	0.001 (3)	0.012 (3)	0.004 (3)
C14	0.035 (3)	0.025 (3)	0.035 (3)	−0.005 (3)	0.017 (3)	−0.005 (3)
C15	0.033 (3)	0.019 (3)	0.026 (3)	−0.003 (2)	0.013 (3)	−0.003 (2)
O16	0.036 (2)	0.028 (2)	0.025 (2)	0.0029 (18)	0.0170 (18)	0.0041 (17)
C18	0.052 (4)	0.048 (4)	0.024 (3)	0.006 (3)	0.017 (3)	0.000 (3)
C2A	0.036 (7)	0.042 (10)	0.040 (7)	0.016 (6)	0.011 (6)	0.011 (6)
C17A	0.041 (13)	0.11 (3)	0.051 (13)	0.040 (15)	0.020 (9)	0.037 (15)

V1—O1	1.612 (4)	C9—C14	1.413 (8)
V1—O2i	1.658 (4)	C9—C10	1.425 (9)
V1—O16	1.915 (4)	C10—C11	1.358 (11)
V1—N1	2.127 (5)	C10—H10A	0.9300
V1—N4	2.183 (4)	C11—C12	1.382 (10)
V1—O2	2.404 (4)	C11—H11A	0.9300
N1—C2B	1.466 (14)	C12—C13	1.383 (9)
N1—C2A	1.498 (13)	C12—H12A	0.9300
N1—H1A	0.9000	C13—C14	1.401 (9)
N1—H1B	0.9000	C13—H13A	0.9300
O2—V1i	1.658 (4)	C14—C15	1.446 (8)
C3—C2B	1.456 (14)	C15—O16	1.320 (6)
C3—N4	1.460 (7)	C18—H18A	0.9600
C3—C2A	1.502 (14)	C18—H18B	0.9600
C3—H3A	0.9700	C18—H18C	0.9600
C3—H3B	0.9700	C2A—C17A	1.52 (6)
N4—C5	1.282 (7)	C2A—H2A	0.9800
C5—C6	1.479 (8)	C17A—H17A	0.9600
C5—C18	1.499 (8)	C17A—H17B	0.9600
C6—C15	1.395 (8)	C17A—H17C	0.9600
C6—C7	1.424 (8)	C2B—C17B	1.59 (6)
C7—C8	1.360 (9)	C2B—H2B	0.9800
C7—H7A	0.9300	C17B—H17D	0.9600
C8—C9	1.413 (9)	C17B—H17E	0.9600
C8—H8A	0.9300	C17B—H17F	0.9600
O1—V1—O2i	107.6 (2)	C9—C8—H8A	119.6
O1—V1—O16	101.6 (2)	C14—C9—C8	119.4 (6)
O2i—V1—O16	100.23 (18)	C14—C9—C10	117.9 (6)
O1—V1—N1	95.9 (2)	C8—C9—C10	122.7 (6)
O2i—V1—N1	92.07 (19)	C11—C10—C9	121.1 (7)
O16—V1—N1	154.36 (19)	C11—C10—H10A	119.5
O1—V1—N4	97.7 (2)	C9—C10—H10A	119.5
O2i—V1—N4	153.32 (19)	C10—C11—C12	121.2 (7)
O16—V1—N4	82.56 (17)	C10—C11—H11A	119.4
N1—V1—N4	76.61 (18)	C12—C11—H11A	119.4
O1—V1—O2	172.50 (19)	C11—C12—C13	119.3 (7)
O2i—V1—O2	77.09 (18)	C11—C12—H12A	120.4
O16—V1—O2	82.98 (15)	C13—C12—H12A	120.4
N1—V1—O2	77.93 (17)	C12—C13—C14	121.5 (7)
N4—V1—O2	76.95 (15)	C12—C13—H13A	119.3
C2B—N1—V1	111.9 (6)	C14—C13—H13A	119.3
C2A—N1—V1	116.4 (5)	C13—C14—C9	119.0 (6)
C2B—N1—H1A	135.2	C13—C14—C15	121.5 (6)
C2A—N1—H1A	108.2	C9—C14—C15	119.5 (5)
V1—N1—H1A	108.2	O16—C15—C6	123.2 (5)
C2B—N1—H1B	78.5	O16—C15—C14	117.4 (5)
C2A—N1—H1B	108.2	C6—C15—C14	119.2 (5)
V1—N1—H1B	108.2	C15—O16—V1	124.1 (3)
H1A—N1—H1B	107.3	C5—C18—H18A	109.5
V1i—O2—V1	102.91 (18)	C5—C18—H18B	109.5
C2B—C3—N4	112.9 (7)	H18A—C18—H18B	109.5
N4—C3—C2A	110.7 (6)	C5—C18—H18C	109.5
C2B—C3—H3A	91.7	H18A—C18—H18C	109.5
N4—C3—H3A	109.0	H18B—C18—H18C	109.5
C2A—C3—H3A	122.4	N1—C2A—C3	108.6 (9)
C2B—C3—H3B	124.2	N1—C2A—C17A	111 (2)
N4—C3—H3B	109.1	C3—C2A—C17A	113 (2)
C2A—C3—H3B	96.8	N1—C2A—H2A	108.0
H3A—C3—H3B	107.7	C3—C2A—H2A	108.0
C5—N4—C3	119.9 (5)	C17A—C2A—H2A	108.0
C5—N4—V1	125.8 (4)	C3—C2B—N1	113.0 (10)
C3—N4—V1	114.3 (3)	C3—C2B—C17B	110 (3)
N4—C5—C6	120.8 (5)	N1—C2B—C17B	111 (2)
N4—C5—C18	123.2 (5)	C3—C2B—H2B	106.6
C6—C5—C18	116.0 (5)	N1—C2B—H2B	106.9
C15—C6—C7	119.5 (5)	C17B—C2B—H2B	108.7
C15—C6—C5	121.0 (5)	C2B—C17B—H17D	109.5
C7—C6—C5	119.6 (5)	C2B—C17B—H17E	109.5
C8—C7—C6	121.3 (6)	H17D—C17B—H17E	109.5
C8—C7—H7A	119.3	C2B—C17B—H17F	109.5
C6—C7—H7A	119.3	H17D—C17B—H17F	109.5
C7—C8—C9	120.8 (6)	H17E—C17B—H17F	109.5
C7—C8—H8A	119.6
O1—V1—N1—C2B	−123.4 (9)	C8—C9—C10—C11	179.6 (7)
O2i—V1—N1—C2B	128.7 (9)	C9—C10—C11—C12	0.4 (11)
O16—V1—N1—C2B	9.6 (10)	C10—C11—C12—C13	1.3 (12)
N4—V1—N1—C2B	−26.9 (9)	C11—C12—C13—C14	−1.8 (11)
O2—V1—N1—C2B	52.3 (9)	C12—C13—C14—C9	0.6 (10)
O1—V1—N1—C2A	−86.0 (9)	C12—C13—C14—C15	179.0 (6)
O2i—V1—N1—C2A	166.1 (9)	C8—C9—C14—C13	180.0 (6)
O16—V1—N1—C2A	47.0 (10)	C10—C9—C14—C13	1.1 (9)
N4—V1—N1—C2A	10.5 (9)	C8—C9—C14—C15	1.5 (9)
O2—V1—N1—C2A	89.8 (9)	C10—C9—C14—C15	−177.4 (6)
O2i—V1—O2—V1i	0.0	C7—C6—C15—O16	−178.0 (5)
O16—V1—O2—V1i	−102.2 (2)	C5—C6—C15—O16	3.1 (8)
N1—V1—O2—V1i	95.0 (2)	C7—C6—C15—C14	5.8 (8)
N4—V1—O2—V1i	173.8 (2)	C5—C6—C15—C14	−173.2 (5)
C2B—C3—N4—C5	−173.8 (10)	C13—C14—C15—O16	−0.3 (8)
C2A—C3—N4—C5	149.1 (9)	C9—C14—C15—O16	178.1 (5)
C2B—C3—N4—V1	3.9 (10)	C13—C14—C15—C6	176.2 (5)
C2A—C3—N4—V1	−33.1 (9)	C9—C14—C15—C6	−5.4 (8)
O1—V1—N4—C5	−75.5 (5)	C6—C15—O16—V1	45.4 (7)
O2i—V1—N4—C5	123.3 (5)	C14—C15—O16—V1	−138.3 (4)
O16—V1—N4—C5	25.3 (5)	O1—V1—O16—C15	47.0 (4)
N1—V1—N4—C5	−169.7 (5)	O2i—V1—O16—C15	157.5 (4)
O2—V1—N4—C5	109.8 (5)	N1—V1—O16—C15	−85.1 (6)
O1—V1—N4—C3	106.9 (4)	N4—V1—O16—C15	−49.4 (4)
O2i—V1—N4—C3	−54.3 (6)	O2—V1—O16—C15	−127.0 (4)
O16—V1—N4—C3	−152.3 (4)	C2B—N1—C2A—C3	59.9 (13)
N1—V1—N4—C3	12.7 (4)	V1—N1—C2A—C3	−30.7 (14)
O2—V1—N4—C3	−67.8 (4)	C2B—N1—C2A—C17A	−65 (2)
C3—N4—C5—C6	−177.8 (5)	V1—N1—C2A—C17A	−155 (2)
V1—N4—C5—C6	4.7 (8)	C2B—C3—C2A—N1	−60.6 (12)
C3—N4—C5—C18	4.2 (9)	N4—C3—C2A—N1	40.1 (13)
V1—N4—C5—C18	−173.3 (4)	C2B—C3—C2A—C17A	63 (2)
N4—C5—C6—C15	−26.7 (8)	N4—C3—C2A—C17A	164 (2)
C18—C5—C6—C15	151.4 (6)	N4—C3—C2B—N1	−27.1 (16)
N4—C5—C6—C7	154.3 (6)	C2A—C3—C2B—N1	66.4 (14)
C18—C5—C6—C7	−27.6 (8)	N4—C3—C2B—C17B	−152.1 (19)
C15—C6—C7—C8	−2.4 (9)	C2A—C3—C2B—C17B	−59 (2)
C5—C6—C7—C8	176.6 (6)	C2A—N1—C2B—C3	−66.9 (14)
C6—C7—C8—C9	−1.6 (10)	V1—N1—C2B—C3	38.2 (15)
C7—C8—C9—C14	2.0 (10)	C2A—N1—C2B—C17B	58 (3)
C7—C8—C9—C10	−179.2 (6)	V1—N1—C2B—C17B	163 (3)
C14—C9—C10—C11	−1.6 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.90	2.19	3.011 (6)	151
C7—H7A···O2iii	0.93	2.41	3.335 (7)	173
C18—H18B···O16iii	0.96	2.56	3.482 (8)	161
C3—H3B···Cg1iii	0.97	2.95	3.874 (7)	159

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
Cg2	Cg2iii	3.518 (4)	0.0	3.365 (4)	1.025 (4)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6-C9/C14/C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.90	2.19	3.011 (6)	151
C7—H7A⋯O2ii	0.93	2.41	3.335 (7)	173
C18—H18B⋯O16ii	0.96	2.56	3.482 (8)	161
C3—H3B⋯Cg1ii	0.97	2.95	3.874 (7)	159

Symmetry codes: (i) ; (ii) .

Table 2

π–π interactions (Å,°)

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
Cg2	Cg2iii	3.518 (4)	0.0	3.365 (4)	1.025 (4)

Symmetry code: (iii) . Notes: Cg2 represents the centroid of the C14–C19 ring. Cg⋯Cg is the distance between ring centroids. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. Offset is the lateral offset distance of ring I from ring J.