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The two title mononuclear oxovanadium (IV) complexes, [VO(C30H22N2O6)(CH3OH)] and [VO(C22H22N2O6)]·H2O, respectively, have distorted square-pyramidal coordination and the 3-carboxy groups form intramolecular hydrogen bonds with the coordinated salicyl O atoms. In (I), methanol coordinates to the vanadium atom trans with respect to the oxo ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005679/qa0271sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005679/qa0271Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005679/qa0271IIsup3.hkl
Contains datablock II

CCDC references: 145643; 145644

Comment top

The structures of dinuclear metal complexes containing the 3-COOH-salen ligand have been reported for homonuclear Cu–Cu (Galy et al., 1979; Gawron et al., 1986) and Ni–Ni (Morgenstern-Badarau et al., 1982) complexes, as well as for heteronuclear Cu–Mg (Beale et al., 1979), Cu–V (Kahn et al., 1982), Cu–Fe (Journaux et al., 1983), Cu–Co (Mikuriya et al., 1978; Galy et al., 1980) and Cu–Ni (Morgenstern-Badarau et al., 1982) complexes, where the inside N2O2 coordination site is occupied by the CuII atom.

The structures of mononuclear metal complexes with 3-COOH-salen were also reported for Fe, which occupies an O4 coordination site (Zarembowitch et al., 1982), and for Co which occupies N2O2 coordination site (Charpin et al., 1988).

The structures of [VO{H2(fsa)2-rac-stien}(MeOH)], (I), and [VO{H2(fsa)2tmen}]·H2O, (II), are reported here [H4(fsa)2-rac-stien is N,N'-bis(3-carboxysalicylidene)-1,2-diphenyl-1,2-ethanediyldiamine and H4(fsa)2tmen is N,N'-bis(3-carboxysalicylidene)-1,1,2,2-tetramethyl-1,2-ethanediyldiamine].

Experimental top

For the preparation of (I), 3-aldehydesalicylic acid was prepared according to the literature method of Duff & Bills (1932). The H4(fsa)2-rac-stien ligand was prepared by the reaction of 3-aldehydesalicylic acid (2 mmol) with 1,2-(±)-diphenylethylenediamine (1 mmol) in ethanol (yield 94%). The oxovanadium(IV) complex was prepared by the reaction of H4(fsa)2-rac-stien (0.5 mmol) with vanadyl sulfate (0.5 mmol) in methanol containing pyridine (yield 92%). Crystals of (I) were grown from a DMSO solution. For the preparation of (II), H4(fsa)2tmen was prepared by the reaction of 3-aldehydesalicylic acid (2 mmol) with 1,1,2,2-tetramethyl-1,2-ethylenediamine (1 mmol) in ethanol (yield 88%). The oxovanadium(IV) complex was prepared by the reaction of H4(fsa)2tmen (0.5 mmol) with vanadyl sulfate (0.5 mmol) in methanol containing pyridine (yield 83%). Crystals of (II) were grown from an acetone solution.

Refinement top

In (I), there is a positional disorder of the C19 and C26 atoms of the five-membered chelate ring moiety. The site-occupancy factors of the C19–C26 and C19*–C26* pairs were estimated to be 81 and 19%, respectively. Namely, the SS– and RR– complexes share the same site with occupancy factors of 81 and 19%, respectively (and vice versa in the centrosymmetric crystal structure). The disorder in the phenyl groups was not taken into account. This caused artificial bond angles, C19*—C20—C21 of 145.4 (6)°, for example. The hydroxyl H atoms were located in difference syntheses and their positional parameters were refined. All the other H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom). The O—H distances are in the range 0.96 (2)–0.98 (3) Å. In (II), all the H atoms were refined isotropically. The O—H and C—H distances are im the ranges 0.76 (4)–0.91 (4) and 0.83 (3)–1.04 (3) Å, respectively. The relatively large Rint value of 0.085 might be due to absorption by a thin glass rod.

Computing details top

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
[VO(C30H22N2O6)(CH3OH)]Dx = 1.431 Mg m3
Mr = 605.50Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/cCell parameters from 24 reflections
a = 9.681 (2) Åθ = 12.8–14.8°
b = 18.474 (2) ŵ = 0.41 mm1
c = 15.786 (2) ÅT = 298 K
β = 95.27 (1)°Prismatic, red
V = 2811.1 (7) Å30.4 × 0.3 × 0.1 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.014
θ–2θ scansθmax = 30°
Absorption correction: ψ scan
(North et al., 1968)
h = 013
Tmin = 0.901, Tmax = 0.960k = 025
8471 measured reflectionsl = 2222
8202 independent reflections3 standard reflections every 150 reflections
4703 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H atoms: see text
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.05P)2 + 1P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.167(Δ/σ)max = 0.001
S = 1.31Δρmax = 0.50 e Å3
8202 reflectionsΔρmin = 0.44 e Å3
397 parameters
Crystal data top
[VO(C30H22N2O6)(CH3OH)]V = 2811.1 (7) Å3
Mr = 605.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.681 (2) ŵ = 0.41 mm1
b = 18.474 (2) ÅT = 298 K
c = 15.786 (2) Å0.4 × 0.3 × 0.1 mm
β = 95.27 (1)°
Data collection top
Rigaku AFC-7R
diffractometer
4703 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.014
Tmin = 0.901, Tmax = 0.9603 standard reflections every 150 reflections
8471 measured reflections intensity decay: none
8202 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056397 parameters
wR(F2) = 0.167H atoms: see text
S = 1.31Δρmax = 0.50 e Å3
8202 reflectionsΔρmin = 0.44 e Å3
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
V10.07892 (5)0.13577 (3)0.46521 (3)0.0360 (1)
O20.1567 (3)0.0675 (1)0.5074 (1)0.0634 (7)
O30.0439 (2)0.1662 (1)0.5514 (1)0.0509 (6)
O40.2123 (2)0.2118 (1)0.4987 (1)0.0439 (5)
O50.2142 (3)0.2502 (2)0.7538 (2)0.0660 (7)
O60.0353 (3)0.2445 (2)0.6791 (2)0.0668 (7)
O70.4932 (3)0.3365 (2)0.6390 (2)0.0718 (8)
O80.3009 (3)0.2736 (2)0.6349 (2)0.0644 (7)
O410.0355 (3)0.2363 (1)0.3973 (2)0.0672 (7)
N90.0845 (3)0.0838 (1)0.4001 (2)0.0437 (6)
N100.1526 (3)0.1296 (1)0.3479 (1)0.0390 (5)
C110.1752 (3)0.1494 (2)0.5592 (2)0.0388 (6)
C120.2384 (3)0.1777 (2)0.6303 (2)0.0393 (6)
C130.1642 (3)0.2259 (2)0.6925 (2)0.0456 (7)
C140.3745 (3)0.1575 (2)0.6423 (2)0.0481 (8)
C150.4518 (3)0.1133 (2)0.5860 (2)0.0510 (8)
C160.3921 (3)0.0884 (2)0.5151 (2)0.0457 (7)
C170.2563 (3)0.1049 (2)0.5002 (2)0.0386 (6)
C180.2056 (3)0.0748 (2)0.4243 (2)0.0461 (7)
C190.0340 (4)0.0409 (2)0.3288 (2)0.037 (1)0.81
C19*0.063 (2)0.0774 (10)0.299 (1)0.03559 (5)*0.19
C200.1477 (3)0.0066 (2)0.2679 (2)0.0487 (8)
C210.1484 (4)0.0666 (2)0.2673 (3)0.068 (1)
C220.2440 (6)0.1038 (3)0.2134 (4)0.101 (2)
C230.3378 (5)0.0664 (3)0.1604 (4)0.092 (2)
C240.3396 (5)0.0061 (3)0.1624 (3)0.081 (1)
C250.2454 (4)0.0437 (2)0.2167 (3)0.065 (1)
C260.0562 (4)0.0928 (2)0.2812 (2)0.0357 (10)0.81
C26*0.090 (2)0.0588 (10)0.306 (1)0.03287 (5)*0.19
C270.1318 (3)0.0519 (2)0.2152 (2)0.0452 (7)
C280.2270 (4)0.0023 (2)0.2337 (3)0.068 (1)
C290.2883 (5)0.0365 (3)0.1704 (4)0.084 (1)
C300.2565 (5)0.0175 (3)0.0878 (3)0.084 (1)
C310.1634 (5)0.0363 (3)0.0668 (2)0.087 (1)
C320.1001 (4)0.0714 (2)0.1314 (2)0.064 (1)
C330.2638 (3)0.1594 (2)0.3272 (2)0.0432 (7)
C340.3562 (3)0.2043 (2)0.3819 (2)0.0375 (6)
C350.4805 (3)0.2256 (2)0.3495 (2)0.0477 (8)
C360.5748 (3)0.2688 (2)0.3960 (2)0.0511 (8)
C370.5485 (3)0.2923 (2)0.4756 (2)0.0490 (8)
C380.4265 (3)0.2734 (2)0.5102 (2)0.0378 (6)
C390.4106 (4)0.2980 (2)0.5994 (2)0.0493 (8)
C400.3281 (3)0.2298 (2)0.4640 (2)0.0354 (6)
C420.0304 (5)0.3085 (3)0.4263 (3)0.091 (2)
H60.013 (4)0.214 (2)0.632 (2)0.0685*
H80.245 (3)0.242 (2)0.595 (2)0.0685*
H140.41590.17620.69140.0572*
H150.54640.10060.59570.0608*
H160.44620.05750.47440.0557*
H180.26800.04380.38940.0535*
H190.02440.00260.35280.0449*0.81
H19*0.08710.12140.26560.0423*0.19
H210.07800.09290.30350.0797*
H220.24590.15680.21520.1216*
H230.40420.09240.12270.1105*
H240.40770.03390.12500.0954*
H250.24850.09610.21920.0766*
H260.00260.12860.25250.0426*0.81
H26*0.11350.01490.34140.0386*0.19
H280.25280.01520.29200.0793*
H290.35630.07450.18490.0988*
H300.30020.04210.04330.0982*
H310.14110.04940.00840.1021*
H320.03130.10880.11680.0772*
H330.28750.15110.27000.0511*
H350.49930.20970.29360.0568*
H360.65970.28240.37320.0643*
H370.61530.32320.50830.0582*
H410.092 (3)0.241 (2)0.344 (1)0.0685*
H42A0.01340.30950.48720.1101*
H42B0.04400.33400.40320.1101*
H42C0.11470.33330.41040.1101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0427 (3)0.0414 (3)0.0242 (2)0.0058 (2)0.0046 (2)0.0008 (2)
O20.088 (2)0.059 (2)0.041 (1)0.007 (1)0.004 (1)0.008 (1)
O30.051 (1)0.063 (1)0.041 (1)0.019 (1)0.0148 (9)0.018 (1)
O40.041 (1)0.062 (1)0.0300 (9)0.0106 (10)0.0072 (8)0.0093 (9)
O50.060 (2)0.097 (2)0.042 (1)0.000 (1)0.012 (1)0.024 (1)
O60.070 (2)0.078 (2)0.056 (1)0.024 (1)0.025 (1)0.032 (1)
O70.080 (2)0.079 (2)0.055 (1)0.031 (2)0.000 (1)0.021 (1)
O80.064 (2)0.088 (2)0.043 (1)0.023 (1)0.012 (1)0.025 (1)
O410.092 (2)0.050 (2)0.054 (1)0.020 (1)0.022 (1)0.008 (1)
N90.048 (1)0.048 (2)0.036 (1)0.012 (1)0.009 (1)0.010 (1)
N100.047 (1)0.044 (1)0.026 (1)0.007 (1)0.0049 (9)0.006 (1)
C110.042 (2)0.041 (2)0.034 (1)0.002 (1)0.007 (1)0.001 (1)
C120.045 (2)0.041 (2)0.033 (1)0.004 (1)0.006 (1)0.004 (1)
C130.054 (2)0.048 (2)0.036 (1)0.000 (1)0.008 (1)0.003 (1)
C140.043 (2)0.061 (2)0.042 (2)0.010 (2)0.010 (1)0.003 (1)
C150.039 (2)0.061 (2)0.055 (2)0.001 (1)0.010 (1)0.005 (2)
C160.045 (2)0.041 (2)0.051 (2)0.007 (1)0.005 (1)0.002 (1)
C170.045 (2)0.032 (1)0.039 (1)0.004 (1)0.007 (1)0.001 (1)
C180.049 (2)0.049 (2)0.041 (2)0.012 (1)0.006 (1)0.010 (1)
C190.052 (2)0.029 (2)0.029 (2)0.000 (2)0.001 (1)0.002 (1)
C200.047 (2)0.057 (2)0.042 (2)0.010 (2)0.006 (1)0.020 (2)
C210.073 (3)0.054 (2)0.076 (3)0.001 (2)0.003 (2)0.004 (2)
C220.098 (4)0.054 (3)0.151 (5)0.018 (3)0.013 (4)0.039 (3)
C230.072 (3)0.099 (4)0.101 (4)0.014 (3)0.015 (3)0.055 (3)
C240.068 (3)0.102 (4)0.069 (3)0.000 (3)0.017 (2)0.005 (3)
C250.060 (2)0.054 (2)0.082 (3)0.002 (2)0.004 (2)0.003 (2)
C260.044 (2)0.037 (2)0.025 (2)0.000 (2)0.001 (1)0.000 (1)
C270.049 (2)0.053 (2)0.033 (1)0.007 (1)0.006 (1)0.012 (1)
C280.068 (2)0.075 (3)0.060 (2)0.015 (2)0.010 (2)0.010 (2)
C290.084 (3)0.065 (3)0.108 (4)0.022 (2)0.031 (3)0.000 (3)
C300.091 (3)0.079 (3)0.089 (3)0.005 (3)0.042 (3)0.040 (3)
C310.104 (4)0.120 (4)0.037 (2)0.004 (3)0.013 (2)0.008 (2)
C320.077 (3)0.071 (3)0.044 (2)0.016 (2)0.010 (2)0.005 (2)
C330.051 (2)0.053 (2)0.026 (1)0.005 (1)0.009 (1)0.001 (1)
C340.041 (2)0.043 (2)0.029 (1)0.001 (1)0.006 (1)0.004 (1)
C350.045 (2)0.064 (2)0.035 (1)0.003 (2)0.011 (1)0.006 (1)
C360.043 (2)0.060 (2)0.052 (2)0.010 (2)0.011 (1)0.006 (2)
C370.045 (2)0.052 (2)0.048 (2)0.011 (1)0.002 (1)0.004 (2)
C380.039 (2)0.039 (2)0.035 (1)0.001 (1)0.000 (1)0.004 (1)
C390.055 (2)0.053 (2)0.039 (2)0.008 (2)0.000 (1)0.007 (1)
C400.037 (1)0.040 (2)0.029 (1)0.000 (1)0.001 (1)0.005 (1)
C420.099 (4)0.054 (3)0.112 (4)0.009 (2)0.032 (3)0.010 (3)
Geometric parameters (Å, º) top
V1—O21.584 (3)C20—C251.370 (5)
V1—O31.969 (2)C21—C221.380 (7)
V1—O41.948 (2)C21—H210.977
V1—O412.368 (3)C22—C231.365 (8)
V1—N92.045 (3)C22—H220.980
V1—N102.048 (2)C23—C241.340 (8)
O3—C111.325 (4)C23—H230.962
O4—C401.334 (4)C24—C251.381 (6)
O5—C131.208 (4)C24—H240.988
O6—C131.330 (4)C25—H250.971
O6—H60.97 (3)C26—C271.527 (5)
O7—C391.201 (4)C26—H260.959
O8—C391.325 (4)C26*—C271.54 (2)
O8—H80.98 (3)C26*—H26*1.00
O41—C421.409 (5)C27—C281.373 (5)
O41—H410.96 (2)C27—C321.378 (4)
N9—C181.276 (4)C28—C291.364 (7)
N9—C191.495 (4)C28—H280.961
N9—C19*1.64 (2)C29—C301.357 (8)
N10—C261.504 (4)C29—H290.975
N10—C26*1.56 (2)C30—C311.362 (7)
N10—C331.277 (4)C30—H300.967
C11—C121.426 (4)C31—C321.398 (6)
C11—C171.423 (4)C31—H310.957
C12—C131.464 (4)C32—H320.973
C12—C141.398 (4)C33—C341.446 (4)
C14—C151.378 (5)C33—H330.964
C14—H140.969C34—C351.406 (4)
C15—C161.384 (5)C34—C401.428 (4)
C15—H150.971C35—C361.373 (5)
C16—C171.391 (4)C35—H350.963
C16—H160.974C36—C371.376 (5)
C17—C181.447 (4)C36—H360.960
C18—H180.967C37—C381.390 (4)
C19—C201.529 (5)C37—H370.973
C19—C261.539 (6)C38—C391.502 (4)
C19—H190.961C38—C401.400 (4)
C19*—C201.60 (2)C42—H42A0.961
C19*—C26*1.51 (2)C42—H42B0.960
C19*—H19*0.984C42—H42C0.950
C20—C211.354 (5)
O2—V1—O3103.3 (1)C22—C21—H21120.3
O2—V1—O4100.5 (1)C21—C22—C23119.8 (5)
O2—V1—O41178.0 (1)C21—C22—H22119.6
O2—V1—N998.9 (1)C23—C22—H22120.6
O2—V1—N1098.3 (1)C22—C23—C24120.0 (5)
O3—V1—O491.94 (9)C22—C23—H23119.7
O3—V1—N989.59 (10)C24—C23—H23120.2
O3—V1—O4178.59 (10)C23—C24—C25120.5 (4)
O3—V1—N10157.40 (10)C23—C24—H24121.1
O4—V1—N9159.68 (10)C25—C24—H24118.4
O4—V1—O4180.10 (9)C20—C25—C24119.8 (4)
O4—V1—N1090.47 (9)C20—C25—H25119.8
N9—V1—N1080.63 (10)C24—C25—H25120.4
O41—V1—N980.35 (10)N10—C26—C19106.5 (3)
O41—V1—N1079.71 (10)N10—C26—C27113.3 (3)
V1—O3—C11130.0 (2)C19—C26—C27110.7 (3)
V1—O4—C40128.9 (2)C19—C26—H26108.8
C13—O6—H6104 (2)C27—C26—H26108.6
C39—O8—H8111 (2)N10—C26*—C19*100 (1)
V1—O41—C42126.4 (3)N10—C26*—C27109 (1)
V1—O41—H41132 (2)N10—C26*—H26*113.0
C42—O41—H41101 (2)C19*—C26*—C27106 (1)
V1—N9—C18126.8 (2)C19*—C26*—H26*113.6
V1—N9—C19109.6 (2)C27—C26*—H26*112.8
V1—N9—C19*111.1 (6)C26—C27—C28124.7 (3)
C18—N9—C19121.9 (3)C26—C27—C32116.5 (3)
C18—N9—C19*119.3 (6)C26*—C27—C2895.1 (7)
V1—N10—C26114.4 (2)C26*—C27—C32145.4 (7)
V1—N10—C26*105.8 (6)C28—C27—C32118.8 (3)
V1—N10—C33125.3 (2)C27—C28—C29120.7 (4)
C26—N10—C33120.0 (2)C27—C28—H28119.7
C26*—N10—C33123.9 (6)C29—C28—H28119.7
O3—C11—C12118.2 (3)C28—C29—C30120.6 (4)
O3—C11—C17123.4 (3)C28—C29—H29119.4
C12—C11—C17118.4 (3)C30—C29—H29120.0
C11—C12—C13122.0 (3)C29—C30—C31120.6 (5)
C11—C12—C14119.1 (3)C29—C30—H30120.0
C13—C12—C14118.8 (3)C31—C30—H30119.3
O5—C13—O6118.8 (3)C30—C31—C32119.0 (4)
O5—C13—C12123.7 (3)C30—C31—H31120.4
O6—C13—C12117.5 (3)C32—C31—H31120.6
C12—C14—C15122.2 (3)C27—C32—C31120.4 (4)
C12—C14—H14118.6C27—C32—H32120.1
C15—C14—H14119.2C31—C32—H32119.6
C14—C15—C16118.5 (3)N10—C33—C34125.8 (3)
C14—C15—H15120.3N10—C33—H33116.7
C16—C15—H15121.2C34—C33—H33117.6
C15—C16—C17122.3 (3)C33—C34—C35116.6 (3)
C15—C16—H16119.2C33—C34—C40124.8 (3)
C17—C16—H16118.5C35—C34—C40118.6 (3)
C11—C17—C16119.3 (3)C34—C35—C36121.2 (3)
C11—C17—C18123.7 (3)C34—C35—H35119.2
C16—C17—C18117.0 (3)C36—C35—H35119.6
N9—C18—C17126.1 (3)C35—C36—C37120.1 (3)
N9—C18—H18116.7C35—C36—H36120.2
C17—C18—H18117.2C37—C36—H36119.7
N9—C19—C20115.2 (3)C36—C37—C38120.9 (3)
N9—C19—C26106.0 (3)C36—C37—H37119.9
N9—C19—H19108.3C38—C37—H37119.1
C20—C19—C26111.0 (3)C37—C38—C39117.1 (3)
C20—C19—H19107.9C37—C38—C40120.2 (3)
C26—C19—H19108.1C39—C38—C40122.6 (3)
N9—C19*—C20104.3 (10)O7—C39—O8120.2 (3)
N9—C19*—C26*98 (1)O7—C39—C38123.1 (3)
N9—C19*—H19*114.5O8—C39—C38116.6 (3)
C20—C19*—C26*108 (1)O4—C40—C34121.9 (2)
C20—C19*—H19*114.8O4—C40—C38119.1 (2)
C26*—C19*—H19*114.7C34—C40—C38119.0 (3)
C19—C20—C21114.9 (3)O41—C42—H42A109.9
C19—C20—C25125.6 (3)O41—C42—H42B110.4
C19*—C20—C21145.4 (6)O41—C42—H42C111.5
C19*—C20—C2594.6 (6)H42A—C42—H42B107.7
C21—C20—C25119.5 (3)H42A—C42—H42C108.6
C20—C21—C22120.3 (4)H42B—C42—H42C108.6
C20—C21—H21119.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O30.97 (4)1.56 (4)2.476 (3)156 (3)
O8—H8···O40.98 (3)1.63 (3)2.514 (3)148 (3)
O41—H41···O5i0.96 (4)1.78 (2)2.732 (3)172 (3)
Symmetry code: (i) x, y+1/2, z1/2.
(II) top
Crystal data top
[VO(C22H22N2O6)]·H2OZ = 2
Mr = 495.37Dx = 1.487 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 10.508 (3) ÅCell parameters from 25 reflections
b = 11.728 (2) Åθ = 14.9–15.0°
c = 9.726 (2) ŵ = 0.50 mm1
α = 107.66 (2)°T = 298 K
β = 96.21 (2)°Prismatic, green
γ = 100.45 (2)°0.5 × 0.4 × 0.3 mm
V = 1106.1 (5) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.085
θ–2θ scansθmax = 30°
Absorption correction: integration
(Coppens et al., 1965)
h = 014
Tmin = 0.860, Tmax = 0.915k = 1616
6772 measured reflectionsl = 1313
6445 independent reflections3 standard reflections every 150 reflections
5528 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0742P)2 + 0.2356P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.70 e Å3
6445 reflectionsΔρmin = 0.64 e Å3
394 parameters
Crystal data top
[VO(C22H22N2O6)]·H2Oγ = 100.45 (2)°
Mr = 495.37V = 1106.1 (5) Å3
Triclinic, P1Z = 2
a = 10.508 (3) ÅMo Kα radiation
b = 11.728 (2) ŵ = 0.50 mm1
c = 9.726 (2) ÅT = 298 K
α = 107.66 (2)°0.5 × 0.4 × 0.3 mm
β = 96.21 (2)°
Data collection top
Rigaku AFC-7R
diffractometer
5528 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.085
Tmin = 0.860, Tmax = 0.9153 standard reflections every 150 reflections
6772 measured reflections intensity decay: none
6445 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039394 parameters
wR(F2) = 0.116All H-atom parameters refined
S = 1.05Δρmax = 0.70 e Å3
6445 reflectionsΔρmin = 0.64 e Å3
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.93844 (2)0.23532 (2)0.43953 (2)0.02608 (8)
O21.0036 (1)0.3126 (1)0.3462 (1)0.0416 (3)
O31.0678 (1)0.2498 (1)0.6074 (1)0.0326 (2)
O40.9638 (1)0.0696 (1)0.3530 (1)0.0355 (2)
O51.4343 (1)0.2904 (1)0.8360 (2)0.0545 (4)
O61.2818 (2)0.1782 (1)0.6463 (2)0.0536 (4)
O71.1604 (2)0.1782 (1)0.1322 (2)0.0585 (4)
O81.1578 (2)0.0317 (2)0.3342 (2)0.0669 (5)
O330.5718 (2)0.1209 (2)0.9139 (3)0.0841 (7)
N90.8510 (1)0.3552 (1)0.5793 (1)0.0267 (2)
N100.7439 (1)0.1686 (1)0.3478 (1)0.0299 (2)
C111.1152 (1)0.3485 (1)0.7264 (2)0.0264 (2)
C121.2410 (1)0.3641 (1)0.8077 (2)0.0295 (3)
C131.3267 (2)0.2754 (2)0.7658 (2)0.0373 (3)
C141.2919 (2)0.4686 (2)0.9299 (2)0.0367 (3)
C151.2216 (2)0.5585 (2)0.9752 (2)0.0383 (3)
C161.0979 (2)0.5422 (1)0.8990 (2)0.0337 (3)
C171.0425 (1)0.4390 (1)0.7751 (2)0.0275 (2)
C180.9116 (1)0.4323 (1)0.7037 (2)0.0294 (3)
C190.7170 (1)0.3616 (1)0.5147 (2)0.0290 (3)
C200.7378 (2)0.4369 (2)0.4117 (2)0.0439 (4)
C210.6416 (2)0.4238 (2)0.6310 (2)0.0421 (4)
C220.6454 (1)0.2253 (1)0.4301 (2)0.0314 (3)
C230.5195 (2)0.2162 (2)0.3277 (2)0.0510 (5)
C240.6139 (2)0.1548 (2)0.5361 (3)0.0486 (4)
C250.7050 (1)0.0797 (2)0.2253 (2)0.0350 (3)
C260.7870 (1)0.0043 (1)0.1483 (2)0.0326 (3)
C270.7338 (2)0.0738 (2)0.0052 (2)0.0414 (4)
C280.8010 (2)0.1537 (2)0.0740 (2)0.0452 (4)
C290.9215 (2)0.1611 (2)0.0074 (2)0.0389 (3)
C300.9760 (2)0.0880 (1)0.1365 (2)0.0324 (3)
C311.1044 (2)0.1032 (2)0.1997 (2)0.0416 (4)
C320.9104 (1)0.0016 (1)0.2160 (2)0.0294 (3)
H61.209 (3)0.175 (3)0.623 (4)0.0900 (1)*
H81.100 (4)0.015 (3)0.369 (4)0.0985 (1)*
H141.374 (2)0.481 (2)0.981 (2)0.04735 (7)*
H151.260 (2)0.630 (2)1.060 (3)0.05258 (8)*
H161.047 (2)0.599 (2)0.924 (3)0.05054 (8)*
H180.872 (2)0.489 (2)0.753 (2)0.03272 (6)*
H20A0.795 (3)0.520 (2)0.464 (3)0.05827 (9)*
H20B0.774 (2)0.401 (2)0.337 (3)0.05209 (8)*
H20C0.657 (3)0.448 (2)0.366 (3)0.06366 (9)*
H21A0.641 (2)0.396 (2)0.710 (3)0.05008 (8)*
H21B0.685 (3)0.515 (3)0.667 (3)0.06448 (9)*
H21C0.551 (3)0.411 (2)0.581 (3)0.06145 (9)*
H23A0.470 (3)0.268 (2)0.377 (3)0.06091 (9)*
H23B0.473 (3)0.142 (2)0.297 (3)0.05343 (8)*
H23C0.537 (3)0.242 (2)0.244 (3)0.06223 (9)*
H24A0.541 (2)0.179 (2)0.583 (3)0.05292 (8)*
H24B0.682 (3)0.173 (3)0.610 (3)0.0667 (1)*
H24C0.587 (3)0.061 (3)0.482 (3)0.06793 (10)*
H250.615 (2)0.052 (2)0.185 (3)0.05270 (8)*
H270.661 (3)0.069 (3)0.032 (3)0.06791 (10)*
H280.768 (3)0.206 (3)0.173 (3)0.06824 (10)*
H290.969 (2)0.206 (2)0.055 (3)0.05341 (8)*
H33A0.532 (4)0.157 (3)0.881 (4)0.0904 (1)*
H33B0.645 (3)0.138 (3)0.897 (3)0.0748 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0208 (1)0.0271 (1)0.0269 (1)0.00825 (8)0.00056 (8)0.00353 (8)
O20.0388 (6)0.0450 (6)0.0425 (6)0.0103 (5)0.0119 (5)0.0146 (5)
O30.0294 (5)0.0295 (5)0.0326 (5)0.0117 (4)0.0050 (4)0.0017 (4)
O40.0314 (5)0.0338 (5)0.0334 (5)0.0158 (4)0.0059 (4)0.0013 (4)
O50.0329 (6)0.0609 (8)0.0643 (9)0.0211 (6)0.0079 (6)0.0124 (7)
O60.0424 (7)0.0525 (8)0.0564 (8)0.0265 (6)0.0051 (6)0.0003 (6)
O70.0472 (7)0.0524 (8)0.0652 (9)0.0313 (6)0.0021 (6)0.0050 (7)
O80.0520 (8)0.0667 (10)0.0601 (9)0.0397 (8)0.0188 (7)0.0161 (7)
O330.0426 (9)0.077 (1)0.157 (2)0.0212 (9)0.016 (1)0.070 (1)
N90.0229 (5)0.0283 (5)0.0293 (5)0.0104 (4)0.0021 (4)0.0081 (4)
N100.0220 (5)0.0311 (6)0.0335 (6)0.0096 (4)0.0004 (4)0.0058 (5)
C110.0247 (6)0.0266 (6)0.0271 (6)0.0060 (5)0.0009 (5)0.0088 (5)
C120.0248 (6)0.0322 (7)0.0305 (6)0.0073 (5)0.0006 (5)0.0102 (5)
C130.0281 (7)0.0423 (8)0.0428 (8)0.0137 (6)0.0015 (6)0.0142 (7)
C140.0288 (7)0.0398 (8)0.0347 (7)0.0057 (6)0.0053 (6)0.0075 (6)
C150.0371 (8)0.0347 (7)0.0329 (7)0.0058 (6)0.0044 (6)0.0014 (6)
C160.0357 (7)0.0298 (7)0.0304 (7)0.0095 (6)0.0003 (5)0.0030 (5)
C170.0257 (6)0.0287 (6)0.0262 (6)0.0076 (5)0.0011 (5)0.0066 (5)
C180.0278 (6)0.0305 (6)0.0291 (6)0.0115 (5)0.0033 (5)0.0065 (5)
C190.0254 (6)0.0323 (6)0.0309 (6)0.0127 (5)0.0015 (5)0.0101 (5)
C200.0438 (9)0.0475 (10)0.0509 (10)0.0163 (8)0.0054 (8)0.0289 (8)
C210.0340 (8)0.0512 (10)0.0403 (8)0.0234 (7)0.0060 (6)0.0061 (7)
C220.0215 (6)0.0328 (7)0.0380 (7)0.0101 (5)0.0023 (5)0.0077 (6)
C230.0281 (7)0.057 (1)0.054 (1)0.0193 (8)0.0094 (7)0.0017 (9)
C240.0424 (9)0.0442 (10)0.069 (1)0.0128 (8)0.0233 (9)0.0269 (9)
C250.0253 (6)0.0354 (7)0.0367 (7)0.0099 (5)0.0041 (5)0.0025 (6)
C260.0286 (6)0.0308 (7)0.0316 (7)0.0093 (5)0.0027 (5)0.0018 (5)
C270.0375 (8)0.0405 (8)0.0355 (8)0.0124 (7)0.0087 (6)0.0001 (6)
C280.0498 (10)0.0411 (9)0.0335 (8)0.0145 (7)0.0053 (7)0.0019 (7)
C290.0446 (9)0.0331 (7)0.0350 (7)0.0156 (6)0.0040 (6)0.0026 (6)
C300.0320 (7)0.0271 (6)0.0354 (7)0.0111 (5)0.0029 (5)0.0048 (5)
C310.0354 (8)0.0367 (8)0.0469 (9)0.0168 (6)0.0005 (7)0.0026 (7)
C320.0276 (6)0.0256 (6)0.0305 (6)0.0078 (5)0.0003 (5)0.0037 (5)
Geometric parameters (Å, º) top
V1—O21.588 (2)C18—H180.89 (2)
V1—O31.952 (1)C19—C201.532 (3)
V1—O41.950 (1)C19—C211.531 (2)
V1—N92.061 (1)C19—C221.558 (2)
V1—N102.047 (1)C20—H20A1.00 (2)
O3—C111.335 (2)C20—H20B0.88 (3)
O4—C321.334 (2)C20—H20C0.96 (3)
O5—C131.210 (2)C21—H21A0.92 (3)
O6—C131.324 (2)C21—H21B1.02 (3)
O6—H60.77 (4)C21—H21C0.99 (3)
O7—C311.213 (3)C22—C231.534 (3)
O8—C311.317 (2)C22—C241.532 (3)
O8—H80.91 (4)C23—H23A0.93 (3)
O33—H33A0.76 (4)C23—H23B0.86 (2)
O33—H33B0.81 (4)C23—H23C0.97 (3)
N9—C181.284 (2)C24—H24A0.97 (3)
N9—C191.503 (2)C24—H24B0.90 (3)
N10—C221.504 (2)C24—H24C1.04 (3)
N10—C251.289 (2)C25—C261.449 (2)
C11—C121.416 (2)C25—H250.94 (2)
C11—C171.415 (2)C26—C271.401 (2)
C12—C131.490 (2)C26—C321.412 (2)
C12—C141.393 (2)C27—C281.375 (3)
C14—C151.387 (3)C27—H270.83 (3)
C14—H140.91 (2)C28—C291.388 (3)
C15—C161.375 (2)C28—H280.96 (2)
C15—H150.96 (2)C29—C301.393 (2)
C16—C171.402 (2)C29—H290.86 (3)
C16—H160.92 (3)C30—C311.485 (3)
C17—C181.449 (2)C30—C321.412 (2)
O2—V1—O3109.44 (6)C19—C20—H20C113 (2)
O2—V1—O4105.60 (6)H20A—C20—H20B108 (2)
O2—V1—N9103.98 (6)H20A—C20—H20C107 (2)
O2—V1—N10107.38 (6)H20B—C20—H20C104 (2)
O3—V1—O486.82 (5)C19—C21—H21A115 (2)
O3—V1—N988.75 (5)C19—C21—H21B106 (2)
O3—V1—N10142.90 (6)C19—C21—H21C107 (2)
O4—V1—N9149.87 (5)H21A—C21—H21B109 (2)
O4—V1—N1087.72 (5)H21A—C21—H21C110 (2)
N9—V1—N1078.08 (5)H21B—C21—H21C110 (2)
V1—O3—C11127.1 (1)N10—C22—C19105.5 (1)
V1—O4—C32123.2 (1)N10—C22—C23112.2 (1)
C13—O6—H6108 (2)N10—C22—C24106.1 (1)
C31—O8—H8108 (2)C19—C22—C23111.6 (2)
H33A—O33—H33B106 (4)C19—C22—C24111.1 (1)
V1—N9—C18123.4 (1)C23—C22—C24110.2 (2)
V1—N9—C19114.75 (8)C22—C23—H23A110 (2)
C18—N9—C19121.1 (1)C22—C23—H23B110 (2)
V1—N10—C22117.64 (8)C22—C23—H23C113 (2)
V1—N10—C25122.1 (1)H23A—C23—H23B109 (2)
C22—N10—C25120.2 (1)H23A—C23—H23C106 (3)
O3—C11—C12119.9 (1)H23B—C23—H23C109 (2)
O3—C11—C17121.7 (1)C22—C24—H24A111 (2)
C12—C11—C17118.4 (1)C22—C24—H24B111 (2)
C11—C12—C13123.0 (1)C22—C24—H24C111 (2)
C11—C12—C14119.9 (1)H24A—C24—H24B106 (2)
C13—C12—C14117.0 (1)H24A—C24—H24C107 (2)
O5—C13—O6120.1 (2)H24B—C24—H24C111 (3)
O5—C13—C12122.2 (1)N10—C25—C26125.4 (1)
O6—C13—C12117.7 (1)N10—C25—H25120 (1)
C12—C14—C15121.5 (1)C26—C25—H25113 (1)
C12—C14—H14121 (1)C25—C26—C27117.2 (1)
C15—C14—H14118 (1)C25—C26—C32122.8 (1)
C14—C15—C16118.9 (1)C27—C26—C32119.8 (1)
C14—C15—H15119 (2)C26—C27—C28121.6 (2)
C16—C15—H15122 (2)C26—C27—H27118 (2)
C15—C16—C17121.9 (2)C28—C27—H27120 (2)
C15—C16—H16122 (1)C27—C28—C29118.9 (1)
C17—C16—H16116 (1)C27—C28—H28123 (2)
C11—C17—C16119.5 (1)C29—C28—H28118 (2)
C11—C17—C18123.8 (1)C28—C29—C30121.3 (2)
C16—C17—C18116.8 (1)C28—C29—H29121 (2)
N9—C18—C17126.4 (1)C30—C29—H29117 (2)
N9—C18—H18119 (1)C29—C30—C31117.7 (2)
C17—C18—H18115 (1)C29—C30—C32120.0 (2)
N9—C19—C20106.7 (1)C31—C30—C32122.3 (1)
N9—C19—C21112.7 (1)O7—C31—O8119.8 (2)
N9—C19—C22104.8 (1)O7—C31—C30122.4 (1)
C20—C19—C21108.9 (2)O8—C31—C30117.8 (2)
C20—C19—C22112.0 (1)O4—C32—C26121.8 (1)
C21—C19—C22111.6 (1)O4—C32—C30119.9 (1)
C19—C20—H20A112 (2)C26—C32—C30118.3 (1)
C19—C20—H20B113 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O30.77 (4)1.87 (4)2.569 (2)152 (3)
O8—H8···O40.91 (4)1.68 (4)2.535 (2)154 (3)
O33—H33A···O5i0.76 (4)2.11 (4)2.886 (3)167 (3)
O33—H33B···O7ii0.81 (4)2.08 (4)2.888 (3)175 (4)
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formula[VO(C30H22N2O6)(CH3OH)][VO(C22H22N2O6)]·H2O
Mr605.50495.37
Crystal system, space groupMonoclinic, P21/cTriclinic, P1
Temperature (K)298298
a, b, c (Å)9.681 (2), 18.474 (2), 15.786 (2)10.508 (3), 11.728 (2), 9.726 (2)
α, β, γ (°)90, 95.27 (1), 90107.66 (2), 96.21 (2), 100.45 (2)
V3)2811.1 (7)1106.1 (5)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.410.50
Crystal size (mm)0.4 × 0.3 × 0.10.5 × 0.4 × 0.3
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Rigaku AFC-7R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Integration
(Coppens et al., 1965)
Tmin, Tmax0.901, 0.9600.860, 0.915
No. of measured, independent and
observed [I > 2σ(I)] reflections
8471, 8202, 4703 6772, 6445, 5528
Rint0.0140.085
(sin θ/λ)max1)0.7030.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.167, 1.31 0.039, 0.116, 1.05
No. of reflections82026445
No. of parameters397394
No. of restraints??
H-atom treatmentH atoms: see textAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.50, 0.440.70, 0.64

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN.

Selected geometric parameters (Å, º) for (I) top
V1—O21.584 (3)V1—O412.368 (3)
V1—O31.969 (2)V1—N92.045 (3)
V1—O41.948 (2)V1—N102.048 (2)
O2—V1—O41178.0 (1)O41—V1—N980.35 (10)
O3—V1—O4178.59 (10)O41—V1—N1079.71 (10)
O4—V1—O4180.10 (9)V1—O41—C42126.4 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O30.97 (4)1.56 (4)2.476 (3)156 (3)
O8—H8···O40.98 (3)1.63 (3)2.514 (3)148 (3)
O41—H41···O5i0.96 (4)1.78 (2)2.732 (3)172 (3)
Symmetry code: (i) x, y+1/2, z1/2.
Selected bond lengths (Å) for (II) top
V1—O21.588 (2)V1—N92.061 (1)
V1—O31.952 (1)V1—N102.047 (1)
V1—O41.950 (1)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O30.77 (4)1.87 (4)2.569 (2)152 (3)
O8—H8···O40.91 (4)1.68 (4)2.535 (2)154 (3)
O33—H33A···O5i0.76 (4)2.11 (4)2.886 (3)167 (3)
O33—H33B···O7ii0.81 (4)2.08 (4)2.888 (3)175 (4)
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z+1.
 

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