(Methanol-κO)(methano-lato-κO)oxido[N-(2-oxidobenzyl-idene)phenyl-alaninato-κO,N,O']vanadium(V).

In the title complex, [V(C(16)H(13)NO(3))(CH(3)O)O(CH(3)OH)], the V(V) atom is six-coordinated by a tridentate ligand derived from the condensation of salicyl-aldehyde and l-phenyl-alanine, a vanadyl O atom, a methano-late O atom and a methanol O atom, forming a distorted octa-hedral coordination geometry. In the crystal, inter-molecular 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 = 397.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.129

S = 1.03

3177 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack (1983 ▶), 1328 Friedel pairs

Flack parameter: 0.04 (4)

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

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

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

[V(C16H13NO3)(CH3O)O(CH4O)]	F(000) = 824
Mr = 397.29	Dx = 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

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

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(Fo2) + (0.0594P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3177 reflections	Δρmax = 0.46 e Å−3
241 parameters	Δρmin = −0.48 e Å−3
0 restraints	Absolute structure: Flack (1983), 1328 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (4)

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .