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The six-coordinated VV atom in the title complex, [VOL(OCH2CH3)(CH3CH2OH)] [H2L = 3-methoxy­salicyl­aldehyde (4-methoxy­benzoyl)­hydrazone] or [VO(C2H5O)(C16H14N2O4)(C2H6O)], displays a distorted octahedral VO(ONO)(O)(O) coordination. The equatorial plane is defined by one N and two O atoms of the tridentate hydrazone ligand and the ethoxy O atom, while the axial oxo group is trans to the ethanol O atom. Adjacent mol­ecules are linked by intermolecular hydrogen bonds into a chain structure along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008839/ww6191sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008839/ww6191Isup2.hkl
Contains datablock I

CCDC reference: 239066

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.060
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C6 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C20 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C20' PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O5 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O6 PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Ethanol(ethoxy)[3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazonato- κ3O,N,O']oxovanadium(V) top
Crystal data top
[VO(C2H5O)(C16H14N2O4)(C2H6O)]F(000) = 952
Mr = 456.36Dx = 1.349 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10711 reflections
a = 19.705 (4) Åθ = 3.6–27.4°
b = 10.328 (2) ŵ = 0.48 mm1
c = 11.148 (2) ÅT = 293 K
β = 97.95 (3)°Prism, red
V = 2247.0 (8) Å30.39 × 0.25 × 0.21 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5081 independent reflections
Radiation source: fine-focus sealed tube3359 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 2425
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1313
Tmin = 0.834, Tmax = 0.905l = 1414
20434 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0749P)2 + 0.5402P]
where P = (Fo2 + 2Fc2)/3
5081 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.36 e Å3
37 restraintsΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
V10.80231 (2)0.45110 (5)0.63396 (4)0.0421 (2)
N10.7286 (1)0.3340 (2)0.4041 (2)0.0463 (6)
N20.7783 (1)0.3019 (2)0.5033 (2)0.0405 (5)
O10.7261 (1)0.5167 (2)0.5185 (2)0.0476 (5)
O20.8425 (1)0.3180 (2)0.7287 (2)0.0462 (5)
O30.5119 (2)0.6902 (3)0.0701 (3)0.100 (1)
O40.9440 (1)0.2408 (2)0.8922 (2)0.0482 (5)
O50.7059 (1)0.3592 (2)0.7130 (2)0.0567 (6)
O60.7932 (1)0.5736 (2)0.7404 (2)0.0610 (6)
O70.8652 (1)0.5019 (2)0.5726 (2)0.0623 (6)
C10.7059 (2)0.4497 (3)0.4218 (2)0.0433 (6)
C20.6535 (2)0.5118 (3)0.3304 (3)0.0480 (7)
C30.6202 (2)0.6222 (3)0.3592 (3)0.0594 (9)
C40.5722 (2)0.6850 (4)0.2756 (3)0.068 (1)
C50.5571 (2)0.6365 (4)0.1610 (3)0.069 (1)
C60.5880 (2)0.5230 (4)0.1319 (3)0.084 (1)
C70.6367 (2)0.4623 (4)0.2146 (3)0.068 (1)
C80.4814 (3)0.8100 (5)0.0910 (4)0.115 (2)
C90.8086 (2)0.1917 (3)0.5005 (2)0.0460 (7)
C100.8614 (2)0.1461 (3)0.5932 (2)0.0455 (7)
C110.8998 (2)0.0358 (3)0.5722 (3)0.0605 (9)
C120.9532 (2)0.0045 (4)0.6565 (3)0.069 (1)
C130.9696 (2)0.0614 (3)0.7644 (3)0.0552 (8)
C140.9322 (2)0.1680 (3)0.7890 (2)0.0422 (6)
C150.8776 (1)0.2133 (3)0.7026 (2)0.0398 (6)
C160.9962 (2)0.1986 (4)0.9855 (3)0.0601 (9)
C170.6436 (7)0.422 (2)0.743 (1)0.102 (3)0.50
C180.6586 (8)0.496 (2)0.858 (2)0.119 (4)0.50
C190.8299 (7)0.6961 (8)0.774 (1)0.099 (3)0.50
C200.7839 (6)0.8026 (8)0.714 (1)0.124 (3)0.50
C17'0.6443 (8)0.435 (2)0.718 (1)0.102 (3)0.50
C18'0.6324 (8)0.461 (2)0.843 (2)0.119 (4)0.50
C19'0.8172 (9)0.7063 (9)0.7231 (9)0.099 (3)0.50
C20'0.8162 (6)0.7842 (9)0.833 (1)0.124 (3)0.50
H30.63010.65600.43700.071*
H40.55050.75960.29770.082*
H60.57590.48660.05560.101*
H70.65820.38780.19230.081*
H8A0.45130.83550.01980.173*
H8B0.51640.87430.10970.173*
H8C0.45570.80180.15780.173*
H90.79540.13810.43440.055*
H110.88910.01030.50040.073*
H120.97850.07700.64080.082*
H131.00610.03360.82050.066*
H16A0.99920.25801.05230.090*
H16B1.03930.19570.95470.090*
H16C0.98510.11391.01230.090*
H17A0.60900.35680.75030.122*0.50
H17B0.62580.48020.67750.122*0.50
H17C0.60520.38910.67580.122*0.50
H17D0.64830.51680.67680.122*0.50
H18A0.61790.53980.87370.178*0.50
H18B0.69410.55780.85070.178*0.50
H18C0.67340.43700.92280.178*0.50
H18D0.62110.55020.85160.178*0.50
H18E0.67310.44030.89790.178*0.50
H18F0.59520.40770.86220.178*0.50
H19A0.87390.69710.74450.118*0.50
H19B0.83720.70700.86120.118*0.50
H19C0.86350.70340.70300.118*0.50
H19D0.78820.74650.65610.118*0.50
H20A0.80550.88500.73190.186*0.50
H20B0.74080.80070.74520.186*0.50
H20C0.77640.78920.62830.186*0.50
H20D0.83280.86970.81920.186*0.50
H20E0.84500.74460.89890.186*0.50
H20F0.77010.78960.85100.186*0.50
H210.711 (2)0.299 (3)0.765 (2)0.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0481 (3)0.0370 (3)0.0385 (3)0.0023 (2)0.0032 (2)0.0029 (2)
N10.052 (1)0.047 (2)0.037 (1)0.001 (1)0.005 (1)0.001 (1)
N20.046 (1)0.042 (1)0.032 (1)0.002 (1)0.002 (1)0.001 (1)
O10.061 (1)0.039 (1)0.040 (1)0.0049 (9)0.0038 (9)0.0003 (9)
O20.055 (1)0.046 (1)0.035 (1)0.0135 (9)0.0031 (9)0.0026 (9)
O30.108 (2)0.103 (2)0.077 (2)0.045 (2)0.033 (2)0.002 (2)
O40.055 (1)0.045 (1)0.041 (1)0.0079 (9)0.0061 (9)0.0032 (9)
O50.054 (1)0.060 (2)0.057 (1)0.011 (1)0.011 (1)0.014 (1)
O60.078 (2)0.043 (1)0.058 (1)0.004 (1)0.002 (1)0.016 (1)
O70.060 (1)0.063 (2)0.064 (1)0.014 (1)0.006 (1)0.001 (1)
C10.045 (2)0.045 (2)0.039 (1)0.000 (1)0.001 (1)0.004 (1)
C20.049 (2)0.050 (2)0.042 (2)0.002 (1)0.003 (1)0.006 (1)
C30.065 (2)0.057 (2)0.052 (2)0.012 (2)0.008 (2)0.003 (2)
C40.071 (2)0.062 (2)0.067 (2)0.019 (2)0.008 (2)0.003 (2)
C50.067 (2)0.074 (3)0.060 (2)0.019 (2)0.012 (2)0.007 (2)
C60.102 (3)0.093 (3)0.048 (2)0.033 (3)0.024 (2)0.009 (2)
C70.082 (2)0.070 (2)0.046 (2)0.025 (2)0.011 (2)0.005 (2)
C80.121 (4)0.116 (4)0.099 (3)0.060 (3)0.020 (3)0.022 (3)
C90.060 (2)0.040 (2)0.037 (1)0.002 (1)0.001 (1)0.006 (1)
C100.056 (2)0.040 (2)0.041 (2)0.006 (1)0.007 (1)0.002 (1)
C110.083 (2)0.047 (2)0.049 (2)0.017 (2)0.000 (2)0.008 (2)
C120.092 (3)0.051 (2)0.062 (2)0.033 (2)0.005 (2)0.003 (2)
C130.065 (2)0.050 (2)0.049 (2)0.015 (2)0.001 (2)0.008 (2)
C140.051 (2)0.036 (2)0.038 (1)0.002 (1)0.004 (1)0.007 (1)
C150.046 (2)0.036 (2)0.038 (1)0.002 (1)0.004 (1)0.004 (1)
C160.064 (2)0.071 (2)0.041 (2)0.013 (2)0.009 (2)0.012 (2)
C170.095 (3)0.125 (5)0.094 (6)0.036 (3)0.044 (3)0.055 (5)
C180.127 (9)0.110 (8)0.129 (5)0.021 (7)0.051 (6)0.017 (5)
C190.146 (6)0.068 (3)0.080 (7)0.017 (4)0.010 (6)0.036 (4)
C200.141 (6)0.084 (5)0.148 (6)0.006 (5)0.026 (5)0.021 (5)
C17'0.095 (3)0.125 (5)0.094 (6)0.036 (3)0.044 (3)0.055 (5)
C18'0.127 (9)0.110 (8)0.129 (5)0.021 (7)0.051 (6)0.017 (5)
C19'0.146 (6)0.068 (3)0.080 (7)0.017 (4)0.010 (6)0.036 (4)
C20'0.141 (6)0.084 (5)0.148 (6)0.006 (5)0.026 (5)0.021 (5)
Geometric parameters (Å, º) top
V1—N22.129 (2)C10—C111.405 (4)
V1—O11.958 (2)C10—C151.402 (4)
V1—O21.844 (2)C11—C121.375 (5)
V1—O52.399 (2)C11—H110.9300
V1—O61.761 (2)C12—C131.381 (5)
V1—O71.586 (2)C12—H120.9300
N1—N21.412 (3)C13—C141.374 (4)
N1—C11.301 (4)C13—H130.9300
N2—C91.287 (4)C14—C151.421 (4)
O1—C11.296 (3)C16—H16A0.9600
O2—C151.338 (3)C16—H16B0.9600
O3—C51.370 (4)C16—H16C0.9600
O3—C81.409 (6)C17—C181.49 (1)
O4—C141.366 (3)C17—H17A0.9700
O4—C161.426 (3)C17—H17B0.9700
O5—C171.465 (8)C18—H18A0.9600
O5—C17'1.451 (9)C18—H18B0.9600
O5—H210.85 (5)C18—H18C0.9600
O6—C19'1.471 (8)C17'—C18'1.471 (9)
O6—C191.479 (8)C17'—H17C0.9700
C1—C21.492 (4)C17'—H17D0.9700
C2—C31.375 (5)C18'—H18D0.9600
C2—C71.385 (4)C18'—H18E0.9600
C3—C41.393 (4)C18'—H18F0.9600
C3—H30.9300C19—C201.518 (9)
C4—C51.367 (5)C19—H19A0.9700
C4—H40.9300C19—H19B0.9700
C5—C61.381 (5)C20—H20A0.9600
C6—C71.385 (5)C20—H20B0.9600
C6—H60.9300C20—H20C0.9600
C7—H70.9300C19'—C20'1.463 (8)
C8—H8A0.9600C19'—H19C0.9700
C8—H8B0.9600C19'—H19D0.9700
C8—H8C0.9600C20'—H20D0.9600
C9—C101.441 (4)C20'—H20E0.9600
C9—H90.9300C20'—H20F0.9600
N2—V1—O581.51 (9)C10—C9—H9117.8
O1—V1—N273.91 (9)C10—C11—H11119.6
O1—V1—O578.67 (8)C10—C15—C14119.2 (3)
O2—V1—N283.68 (9)C11—C10—C9119.9 (3)
O2—V1—O1149.7 (1)C11—C12—C13120.8 (3)
O2—V1—O578.10 (9)C11—C12—H12119.6
O6—V1—N2161.4 (1)C12—C11—C10120.7 (3)
O6—V1—O193.1 (1)C12—C11—H11119.6
O6—V1—O2103.0 (1)C12—C13—H13120.0
O6—V1—O582.9 (1)C13—C12—H12119.6
O7—V1—N293.3 (1)C13—C14—C15120.3 (3)
O7—V1—O1100.2 (1)C14—O4—C16117.9 (2)
O7—V1—O2101.2 (1)C14—C13—C12120.1 (3)
O7—V1—O5174.8 (1)C14—C13—H13120.0
O7—V1—O6102.2 (1)C15—O2—V1132.2 (2)
V1—O5—H21122 (2)C15—C10—C11118.9 (3)
N1—N2—V1115.5 (2)C15—C10—C9121.1 (3)
N1—C1—C2120.7 (3)C17—O5—V1130 (1)
N2—C9—C10124.3 (3)C17—O5—H21101 (3)
N2—C9—H9117.8C17—C18—H18A109.5
O1—C1—N1123.0 (3)C17—C18—H18B109.5
O1—C1—C2116.3 (3)C17—C18—H18C109.5
O2—C15—C10121.8 (2)C18—C17—H17A109.6
O2—C15—C14119.0 (2)C18—C17—H17B109.6
O3—C5—C6115.7 (3)C19—O6—V1133.9 (6)
O3—C8—H8A109.5C19—C20—H20A109.5
O3—C8—H8B109.5C19—C20—H20B109.5
O3—C8—H8C109.5C19—C20—H20C109.5
O4—C14—C13125.2 (3)C20—C19—H19A110.6
O4—C14—C15114.5 (2)C20—C19—H19B110.6
O4—C16—H16A109.5C17'—O5—V1121 (1)
O4—C16—H16B109.5C17'—O5—H21112 (3)
O4—C16—H16C109.5C17'—C18'—H18D109.5
O5—C17—C18110.4 (9)C17'—C18'—H18E109.5
O5—C17—H17A109.6C17'—C18'—H18F109.5
O5—C17—H17B109.6C18'—C17'—H17C109.2
O5—C17'—C18'112.2 (9)C18'—C17'—H17D109.2
O5—C17'—H17C109.2C19'—O6—V1121.1 (5)
O5—C17'—H17D109.2C19'—C20'—H20D109.5
O6—C19—C20105.5 (7)C19'—C20'—H20E109.5
O6—C19—H19A110.6C19'—C20'—H20F109.5
O6—C19—H19B110.6C20'—C19'—O6111.2 (8)
O6—C19'—H19C109.4C20'—C19'—H19C109.4
O6—C19'—H19D109.4C20'—C19'—H19D109.4
C1—N1—N2108.2 (2)H8A—C8—H8B109.5
C1—O1—V1118.8 (2)H8A—C8—H8C109.5
C2—C3—C4122.1 (3)H8B—C8—H8C109.5
C2—C3—H3118.9H16A—C16—H16B109.5
C2—C7—C6120.5 (3)H16A—C16—H16C109.5
C2—C7—H7119.7H16B—C16—H16C109.5
C3—C2—C1120.2 (3)H17A—C17—H17B108.1
C3—C2—C7117.6 (3)H17C—C17'—H17D107.9
C3—C4—H4120.2H18A—C18—H18B109.5
C4—C3—H3118.9H18A—C18—H18C109.5
C4—C5—O3125.3 (4)H18B—C18—H18C109.5
C4—C5—C6119.0 (3)H18D—C18'—H18E109.5
C5—O3—C8118.8 (3)H18D—C18'—H18F109.5
C5—C4—C3119.7 (3)H18E—C18'—H18F109.5
C5—C4—H4120.2H19A—C19—H19B108.8
C5—C6—C7121.0 (3)H19C—C19'—H19D108.0
C5—C6—H6119.5H20A—C20—H20B109.5
C6—C7—H7119.7H20A—C20—H20C109.5
C7—C2—C1122.2 (3)H20B—C20—H20C109.5
C7—C6—H6119.5H20D—C20'—H20E109.5
C9—N2—V1126.6 (2)H20D—C20'—H20F109.5
C9—N2—N1117.6 (2)H20E—C20'—H20F109.5
V1—N2—C9—C105.3 (4)O5—V1—O6—C19179.1 (6)
V1—O1—C1—N17.9 (4)O5—V1—O6—C19'154.4 (8)
V1—O1—C1—C2172.9 (2)O6—V1—N2—N152.9 (4)
V1—O2—C15—C1035.6 (4)O6—V1—N2—C9133.7 (3)
V1—O2—C15—C14145.4 (2)O6—V1—O1—C1173.5 (2)
V1—O5—C17—C1876 (2)O6—V1—O2—C15160.6 (2)
V1—O5—C17'—C18'114 (2)O6—V1—O5—C1743.1 (8)
V1—O6—C19—C20102.5 (10)O6—V1—O5—C17'52.8 (8)
V1—O6—C19'—C20'169.3 (9)O7—V1—N2—N193.8 (2)
N1—N2—C9—C10178.6 (3)O7—V1—N2—C979.6 (3)
N1—C1—C2—C3167.5 (3)O7—V1—O1—C183.5 (2)
N1—C1—C2—C712.8 (5)O7—V1—O2—C1555.1 (3)
N2—V1—O1—C17.1 (2)O7—V1—O6—C190.1 (6)
N2—V1—O2—C1537.1 (3)O7—V1—O6—C19'24.9 (8)
N2—V1—O5—C17126.7 (8)C1—N1—N2—V13.8 (3)
N2—V1—O5—C17'116.9 (8)C1—N1—N2—C9177.9 (3)
N2—V1—O6—C19145.7 (6)C1—C2—C3—C4178.4 (3)
N2—V1—O6—C19'120.9 (8)C1—C2—C7—C6179.7 (4)
N2—N1—C1—O12.2 (4)C2—C3—C4—C50.0 (6)
N2—N1—C1—C2178.6 (2)C3—C2—C7—C60.0 (6)
N2—C9—C10—C158.5 (5)C3—C4—C5—O3178.8 (4)
N2—C9—C10—C11168.5 (3)C3—C4—C5—C62.5 (7)
O1—V1—N2—N15.9 (2)C4—C5—C6—C73.8 (7)
O1—V1—N2—C9179.3 (3)C5—C6—C7—C22.5 (7)
O1—V1—O2—C1579.1 (3)C7—C2—C3—C41.3 (6)
O1—V1—O5—C1751.5 (8)C8—O3—C5—C44.8 (7)
O1—V1—O5—C17'41.7 (8)C8—O3—C5—C6176.4 (5)
O1—V1—O6—C19101.0 (6)C9—C10—C11—C12176.0 (3)
O1—V1—O6—C19'76.2 (8)C9—C10—C15—O23.9 (4)
O1—C1—C2—C311.7 (4)C9—C10—C15—C14177.1 (3)
O1—C1—C2—C7168.0 (3)C10—C11—C12—C130.8 (6)
O2—V1—N2—N1165.3 (2)C11—C10—C15—O2179.2 (3)
O2—V1—N2—C921.3 (3)C11—C10—C15—C140.2 (4)
O2—V1—O1—C150.9 (3)C11—C12—C13—C140.5 (6)
O2—V1—O5—C17148.1 (8)C12—C13—C14—O4179.7 (3)
O2—V1—O5—C17'157.8 (8)C12—C13—C14—C151.7 (5)
O2—V1—O6—C19104.9 (6)C13—C14—C15—O2179.5 (3)
O2—V1—O6—C19'129.6 (8)C13—C14—C15—C101.5 (4)
O3—C5—C6—C7177.3 (4)C15—C10—C11—C121.0 (5)
O4—C14—C15—O21.2 (4)C16—O4—C14—C134.3 (4)
O4—C14—C15—C10179.7 (2)C16—O4—C14—C15177.5 (3)
O5—V1—N2—N186.4 (2)C17—O5—C17'—C18'27 (7)
O5—V1—N2—C9100.1 (3)C19—O6—C19'—C20'39 (2)
O5—V1—O1—C191.4 (2)C17'—O5—C17—C18120 (5)
O5—V1—O2—C15119.7 (3)C19'—O6—C19—C2037 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H21···N1i0.85 (3)2.07 (3)2.908 (3)174 (4)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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