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
CCDC references: 145643; 145644
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.
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.
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.
Crystal data top
[VO(C30H22N2O6)(CH3OH)] | Dx = 1.431 Mg m−3 |
Mr = 605.50 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/c | Cell parameters from 24 reflections |
a = 9.681 (2) Å | θ = 12.8–14.8° |
b = 18.474 (2) Å | µ = 0.41 mm−1 |
c = 15.786 (2) Å | T = 298 K |
β = 95.27 (1)° | Prismatic, red |
V = 2811.1 (7) Å3 | 0.4 × 0.3 × 0.1 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.014 |
θ–2θ scans | θmax = 30° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→13 |
Tmin = 0.901, Tmax = 0.960 | k = 0→25 |
8471 measured reflections | l = −22→22 |
8202 independent reflections | 3 standard reflections every 150 reflections |
4703 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H 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 = 1.31 | Δρmax = 0.50 e Å−3 |
8202 reflections | Δρmin = −0.44 e Å−3 |
397 parameters | |
Crystal data top
[VO(C30H22N2O6)(CH3OH)] | V = 2811.1 (7) Å3 |
Mr = 605.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.681 (2) Å | µ = 0.41 mm−1 |
b = 18.474 (2) Å | T = 298 K |
c = 15.786 (2) Å | 0.4 × 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 = 0.960 | 3 standard reflections every 150 reflections |
8471 measured reflections | intensity decay: none |
8202 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 397 parameters |
wR(F2) = 0.167 | H atoms: see text |
S = 1.31 | Δρmax = 0.50 e Å−3 |
8202 reflections | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
V1 | 0.07892 (5) | 0.13577 (3) | 0.46521 (3) | 0.0360 (1) | |
O2 | 0.1567 (3) | 0.0675 (1) | 0.5074 (1) | 0.0634 (7) | |
O3 | −0.0439 (2) | 0.1662 (1) | 0.5514 (1) | 0.0509 (6) | |
O4 | 0.2123 (2) | 0.2118 (1) | 0.4987 (1) | 0.0439 (5) | |
O5 | −0.2142 (3) | 0.2502 (2) | 0.7538 (2) | 0.0660 (7) | |
O6 | −0.0353 (3) | 0.2445 (2) | 0.6791 (2) | 0.0668 (7) | |
O7 | 0.4932 (3) | 0.3365 (2) | 0.6390 (2) | 0.0718 (8) | |
O8 | 0.3009 (3) | 0.2736 (2) | 0.6349 (2) | 0.0644 (7) | |
O41 | −0.0355 (3) | 0.2363 (1) | 0.3973 (2) | 0.0672 (7) | |
N9 | −0.0845 (3) | 0.0838 (1) | 0.4001 (2) | 0.0437 (6) | |
N10 | 0.1526 (3) | 0.1296 (1) | 0.3479 (1) | 0.0390 (5) | |
C11 | −0.1752 (3) | 0.1494 (2) | 0.5592 (2) | 0.0388 (6) | |
C12 | −0.2384 (3) | 0.1777 (2) | 0.6303 (2) | 0.0393 (6) | |
C13 | −0.1642 (3) | 0.2259 (2) | 0.6925 (2) | 0.0456 (7) | |
C14 | −0.3745 (3) | 0.1575 (2) | 0.6423 (2) | 0.0481 (8) | |
C15 | −0.4518 (3) | 0.1133 (2) | 0.5860 (2) | 0.0510 (8) | |
C16 | −0.3921 (3) | 0.0884 (2) | 0.5151 (2) | 0.0457 (7) | |
C17 | −0.2563 (3) | 0.1049 (2) | 0.5002 (2) | 0.0386 (6) | |
C18 | −0.2056 (3) | 0.0748 (2) | 0.4243 (2) | 0.0461 (7) | |
C19 | −0.0340 (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 |
C20 | −0.1477 (3) | 0.0066 (2) | 0.2679 (2) | 0.0487 (8) | |
C21 | −0.1484 (4) | −0.0666 (2) | 0.2673 (3) | 0.068 (1) | |
C22 | −0.2440 (6) | −0.1038 (3) | 0.2134 (4) | 0.101 (2) | |
C23 | −0.3378 (5) | −0.0664 (3) | 0.1604 (4) | 0.092 (2) | |
C24 | −0.3396 (5) | 0.0061 (3) | 0.1624 (3) | 0.081 (1) | |
C25 | −0.2454 (4) | 0.0437 (2) | 0.2167 (3) | 0.065 (1) | |
C26 | 0.0562 (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 |
C27 | 0.1318 (3) | 0.0519 (2) | 0.2152 (2) | 0.0452 (7) | |
C28 | 0.2270 (4) | −0.0023 (2) | 0.2337 (3) | 0.068 (1) | |
C29 | 0.2883 (5) | −0.0365 (3) | 0.1704 (4) | 0.084 (1) | |
C30 | 0.2565 (5) | −0.0175 (3) | 0.0878 (3) | 0.084 (1) | |
C31 | 0.1634 (5) | 0.0363 (3) | 0.0668 (2) | 0.087 (1) | |
C32 | 0.1001 (4) | 0.0714 (2) | 0.1314 (2) | 0.064 (1) | |
C33 | 0.2638 (3) | 0.1594 (2) | 0.3272 (2) | 0.0432 (7) | |
C34 | 0.3562 (3) | 0.2043 (2) | 0.3819 (2) | 0.0375 (6) | |
C35 | 0.4805 (3) | 0.2256 (2) | 0.3495 (2) | 0.0477 (8) | |
C36 | 0.5748 (3) | 0.2688 (2) | 0.3960 (2) | 0.0511 (8) | |
C37 | 0.5485 (3) | 0.2923 (2) | 0.4756 (2) | 0.0490 (8) | |
C38 | 0.4265 (3) | 0.2734 (2) | 0.5102 (2) | 0.0378 (6) | |
C39 | 0.4106 (4) | 0.2980 (2) | 0.5994 (2) | 0.0493 (8) | |
C40 | 0.3281 (3) | 0.2298 (2) | 0.4640 (2) | 0.0354 (6) | |
C42 | −0.0304 (5) | 0.3085 (3) | 0.4263 (3) | 0.091 (2) | |
H6 | −0.013 (4) | 0.214 (2) | 0.632 (2) | 0.0685* | |
H8 | 0.245 (3) | 0.242 (2) | 0.595 (2) | 0.0685* | |
H14 | −0.4159 | 0.1762 | 0.6914 | 0.0572* | |
H15 | −0.5464 | 0.1006 | 0.5957 | 0.0608* | |
H16 | −0.4462 | 0.0575 | 0.4744 | 0.0557* | |
H18 | −0.2680 | 0.0438 | 0.3894 | 0.0535* | |
H19 | 0.0244 | 0.0026 | 0.3528 | 0.0449* | 0.81 |
H19* | −0.0871 | 0.1214 | 0.2656 | 0.0423* | 0.19 |
H21 | −0.0780 | −0.0929 | 0.3035 | 0.0797* | |
H22 | −0.2459 | −0.1568 | 0.2152 | 0.1216* | |
H23 | −0.4042 | −0.0924 | 0.1227 | 0.1105* | |
H24 | −0.4077 | 0.0339 | 0.1250 | 0.0954* | |
H25 | −0.2485 | 0.0961 | 0.2192 | 0.0766* | |
H26 | −0.0026 | 0.1286 | 0.2525 | 0.0426* | 0.81 |
H26* | 0.1135 | 0.0149 | 0.3414 | 0.0386* | 0.19 |
H28 | 0.2528 | −0.0152 | 0.2920 | 0.0793* | |
H29 | 0.3563 | −0.0745 | 0.1849 | 0.0988* | |
H30 | 0.3002 | −0.0421 | 0.0433 | 0.0982* | |
H31 | 0.1411 | 0.0494 | 0.0084 | 0.1021* | |
H32 | 0.0313 | 0.1088 | 0.1168 | 0.0772* | |
H33 | 0.2875 | 0.1511 | 0.2700 | 0.0511* | |
H35 | 0.4993 | 0.2097 | 0.2936 | 0.0568* | |
H36 | 0.6597 | 0.2824 | 0.3732 | 0.0643* | |
H37 | 0.6153 | 0.3232 | 0.5083 | 0.0582* | |
H41 | −0.092 (3) | 0.241 (2) | 0.344 (1) | 0.0685* | |
H42A | −0.0134 | 0.3095 | 0.4872 | 0.1101* | |
H42B | 0.0440 | 0.3340 | 0.4032 | 0.1101* | |
H42C | −0.1147 | 0.3333 | 0.4104 | 0.1101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
V1 | 0.0427 (3) | 0.0414 (3) | 0.0242 (2) | −0.0058 (2) | 0.0046 (2) | −0.0008 (2) |
O2 | 0.088 (2) | 0.059 (2) | 0.041 (1) | 0.007 (1) | −0.004 (1) | 0.008 (1) |
O3 | 0.051 (1) | 0.063 (1) | 0.041 (1) | −0.019 (1) | 0.0148 (9) | −0.018 (1) |
O4 | 0.041 (1) | 0.062 (1) | 0.0300 (9) | −0.0106 (10) | 0.0072 (8) | −0.0093 (9) |
O5 | 0.060 (2) | 0.097 (2) | 0.042 (1) | 0.000 (1) | 0.012 (1) | −0.024 (1) |
O6 | 0.070 (2) | 0.078 (2) | 0.056 (1) | −0.024 (1) | 0.025 (1) | −0.032 (1) |
O7 | 0.080 (2) | 0.079 (2) | 0.055 (1) | −0.031 (2) | 0.000 (1) | −0.021 (1) |
O8 | 0.064 (2) | 0.088 (2) | 0.043 (1) | −0.023 (1) | 0.012 (1) | −0.025 (1) |
O41 | 0.092 (2) | 0.050 (2) | 0.054 (1) | 0.020 (1) | −0.022 (1) | −0.008 (1) |
N9 | 0.048 (1) | 0.048 (2) | 0.036 (1) | −0.012 (1) | 0.009 (1) | −0.010 (1) |
N10 | 0.047 (1) | 0.044 (1) | 0.026 (1) | −0.007 (1) | 0.0049 (9) | −0.006 (1) |
C11 | 0.042 (2) | 0.041 (2) | 0.034 (1) | −0.002 (1) | 0.007 (1) | 0.001 (1) |
C12 | 0.045 (2) | 0.041 (2) | 0.033 (1) | 0.004 (1) | 0.006 (1) | 0.004 (1) |
C13 | 0.054 (2) | 0.048 (2) | 0.036 (1) | 0.000 (1) | 0.008 (1) | −0.003 (1) |
C14 | 0.043 (2) | 0.061 (2) | 0.042 (2) | 0.010 (2) | 0.010 (1) | 0.003 (1) |
C15 | 0.039 (2) | 0.061 (2) | 0.055 (2) | −0.001 (1) | 0.010 (1) | 0.005 (2) |
C16 | 0.045 (2) | 0.041 (2) | 0.051 (2) | −0.007 (1) | 0.005 (1) | −0.002 (1) |
C17 | 0.045 (2) | 0.032 (1) | 0.039 (1) | −0.004 (1) | 0.007 (1) | 0.001 (1) |
C18 | 0.049 (2) | 0.049 (2) | 0.041 (2) | −0.012 (1) | 0.006 (1) | −0.010 (1) |
C19 | 0.052 (2) | 0.029 (2) | 0.029 (2) | 0.000 (2) | 0.001 (1) | −0.002 (1) |
C20 | 0.047 (2) | 0.057 (2) | 0.042 (2) | −0.010 (2) | 0.006 (1) | −0.020 (2) |
C21 | 0.073 (3) | 0.054 (2) | 0.076 (3) | −0.001 (2) | −0.003 (2) | 0.004 (2) |
C22 | 0.098 (4) | 0.054 (3) | 0.151 (5) | −0.018 (3) | 0.013 (4) | −0.039 (3) |
C23 | 0.072 (3) | 0.099 (4) | 0.101 (4) | −0.014 (3) | −0.015 (3) | −0.055 (3) |
C24 | 0.068 (3) | 0.102 (4) | 0.069 (3) | 0.000 (3) | −0.017 (2) | −0.005 (3) |
C25 | 0.060 (2) | 0.054 (2) | 0.082 (3) | −0.002 (2) | 0.004 (2) | −0.003 (2) |
C26 | 0.044 (2) | 0.037 (2) | 0.025 (2) | 0.000 (2) | 0.001 (1) | 0.000 (1) |
C27 | 0.049 (2) | 0.053 (2) | 0.033 (1) | −0.007 (1) | 0.006 (1) | −0.012 (1) |
C28 | 0.068 (2) | 0.075 (3) | 0.060 (2) | 0.015 (2) | 0.010 (2) | 0.010 (2) |
C29 | 0.084 (3) | 0.065 (3) | 0.108 (4) | 0.022 (2) | 0.031 (3) | 0.000 (3) |
C30 | 0.091 (3) | 0.079 (3) | 0.089 (3) | −0.005 (3) | 0.042 (3) | −0.040 (3) |
C31 | 0.104 (4) | 0.120 (4) | 0.037 (2) | −0.004 (3) | 0.013 (2) | −0.008 (2) |
C32 | 0.077 (3) | 0.071 (3) | 0.044 (2) | 0.016 (2) | 0.010 (2) | 0.005 (2) |
C33 | 0.051 (2) | 0.053 (2) | 0.026 (1) | −0.005 (1) | 0.009 (1) | −0.001 (1) |
C34 | 0.041 (2) | 0.043 (2) | 0.029 (1) | −0.001 (1) | 0.006 (1) | 0.004 (1) |
C35 | 0.045 (2) | 0.064 (2) | 0.035 (1) | −0.003 (2) | 0.011 (1) | 0.006 (1) |
C36 | 0.043 (2) | 0.060 (2) | 0.052 (2) | −0.010 (2) | 0.011 (1) | 0.006 (2) |
C37 | 0.045 (2) | 0.052 (2) | 0.048 (2) | −0.011 (1) | −0.002 (1) | 0.004 (2) |
C38 | 0.039 (2) | 0.039 (2) | 0.035 (1) | −0.001 (1) | 0.000 (1) | 0.004 (1) |
C39 | 0.055 (2) | 0.053 (2) | 0.039 (2) | −0.008 (2) | 0.000 (1) | −0.007 (1) |
C40 | 0.037 (1) | 0.040 (2) | 0.029 (1) | 0.000 (1) | 0.001 (1) | 0.005 (1) |
C42 | 0.099 (4) | 0.054 (3) | 0.112 (4) | 0.009 (2) | −0.032 (3) | −0.010 (3) |
Geometric parameters (Å, º) top
V1—O2 | 1.584 (3) | C20—C25 | 1.370 (5) |
V1—O3 | 1.969 (2) | C21—C22 | 1.380 (7) |
V1—O4 | 1.948 (2) | C21—H21 | 0.977 |
V1—O41 | 2.368 (3) | C22—C23 | 1.365 (8) |
V1—N9 | 2.045 (3) | C22—H22 | 0.980 |
V1—N10 | 2.048 (2) | C23—C24 | 1.340 (8) |
O3—C11 | 1.325 (4) | C23—H23 | 0.962 |
O4—C40 | 1.334 (4) | C24—C25 | 1.381 (6) |
O5—C13 | 1.208 (4) | C24—H24 | 0.988 |
O6—C13 | 1.330 (4) | C25—H25 | 0.971 |
O6—H6 | 0.97 (3) | C26—C27 | 1.527 (5) |
O7—C39 | 1.201 (4) | C26—H26 | 0.959 |
O8—C39 | 1.325 (4) | C26*—C27 | 1.54 (2) |
O8—H8 | 0.98 (3) | C26*—H26* | 1.00 |
O41—C42 | 1.409 (5) | C27—C28 | 1.373 (5) |
O41—H41 | 0.96 (2) | C27—C32 | 1.378 (4) |
N9—C18 | 1.276 (4) | C28—C29 | 1.364 (7) |
N9—C19 | 1.495 (4) | C28—H28 | 0.961 |
N9—C19* | 1.64 (2) | C29—C30 | 1.357 (8) |
N10—C26 | 1.504 (4) | C29—H29 | 0.975 |
N10—C26* | 1.56 (2) | C30—C31 | 1.362 (7) |
N10—C33 | 1.277 (4) | C30—H30 | 0.967 |
C11—C12 | 1.426 (4) | C31—C32 | 1.398 (6) |
C11—C17 | 1.423 (4) | C31—H31 | 0.957 |
C12—C13 | 1.464 (4) | C32—H32 | 0.973 |
C12—C14 | 1.398 (4) | C33—C34 | 1.446 (4) |
C14—C15 | 1.378 (5) | C33—H33 | 0.964 |
C14—H14 | 0.969 | C34—C35 | 1.406 (4) |
C15—C16 | 1.384 (5) | C34—C40 | 1.428 (4) |
C15—H15 | 0.971 | C35—C36 | 1.373 (5) |
C16—C17 | 1.391 (4) | C35—H35 | 0.963 |
C16—H16 | 0.974 | C36—C37 | 1.376 (5) |
C17—C18 | 1.447 (4) | C36—H36 | 0.960 |
C18—H18 | 0.967 | C37—C38 | 1.390 (4) |
C19—C20 | 1.529 (5) | C37—H37 | 0.973 |
C19—C26 | 1.539 (6) | C38—C39 | 1.502 (4) |
C19—H19 | 0.961 | C38—C40 | 1.400 (4) |
C19*—C20 | 1.60 (2) | C42—H42A | 0.961 |
C19*—C26* | 1.51 (2) | C42—H42B | 0.960 |
C19*—H19* | 0.984 | C42—H42C | 0.950 |
C20—C21 | 1.354 (5) | | |
| | | |
O2—V1—O3 | 103.3 (1) | C22—C21—H21 | 120.3 |
O2—V1—O4 | 100.5 (1) | C21—C22—C23 | 119.8 (5) |
O2—V1—O41 | 178.0 (1) | C21—C22—H22 | 119.6 |
O2—V1—N9 | 98.9 (1) | C23—C22—H22 | 120.6 |
O2—V1—N10 | 98.3 (1) | C22—C23—C24 | 120.0 (5) |
O3—V1—O4 | 91.94 (9) | C22—C23—H23 | 119.7 |
O3—V1—N9 | 89.59 (10) | C24—C23—H23 | 120.2 |
O3—V1—O41 | 78.59 (10) | C23—C24—C25 | 120.5 (4) |
O3—V1—N10 | 157.40 (10) | C23—C24—H24 | 121.1 |
O4—V1—N9 | 159.68 (10) | C25—C24—H24 | 118.4 |
O4—V1—O41 | 80.10 (9) | C20—C25—C24 | 119.8 (4) |
O4—V1—N10 | 90.47 (9) | C20—C25—H25 | 119.8 |
N9—V1—N10 | 80.63 (10) | C24—C25—H25 | 120.4 |
O41—V1—N9 | 80.35 (10) | N10—C26—C19 | 106.5 (3) |
O41—V1—N10 | 79.71 (10) | N10—C26—C27 | 113.3 (3) |
V1—O3—C11 | 130.0 (2) | C19—C26—C27 | 110.7 (3) |
V1—O4—C40 | 128.9 (2) | C19—C26—H26 | 108.8 |
C13—O6—H6 | 104 (2) | C27—C26—H26 | 108.6 |
C39—O8—H8 | 111 (2) | N10—C26*—C19* | 100 (1) |
V1—O41—C42 | 126.4 (3) | N10—C26*—C27 | 109 (1) |
V1—O41—H41 | 132 (2) | N10—C26*—H26* | 113.0 |
C42—O41—H41 | 101 (2) | C19*—C26*—C27 | 106 (1) |
V1—N9—C18 | 126.8 (2) | C19*—C26*—H26* | 113.6 |
V1—N9—C19 | 109.6 (2) | C27—C26*—H26* | 112.8 |
V1—N9—C19* | 111.1 (6) | C26—C27—C28 | 124.7 (3) |
C18—N9—C19 | 121.9 (3) | C26—C27—C32 | 116.5 (3) |
C18—N9—C19* | 119.3 (6) | C26*—C27—C28 | 95.1 (7) |
V1—N10—C26 | 114.4 (2) | C26*—C27—C32 | 145.4 (7) |
V1—N10—C26* | 105.8 (6) | C28—C27—C32 | 118.8 (3) |
V1—N10—C33 | 125.3 (2) | C27—C28—C29 | 120.7 (4) |
C26—N10—C33 | 120.0 (2) | C27—C28—H28 | 119.7 |
C26*—N10—C33 | 123.9 (6) | C29—C28—H28 | 119.7 |
O3—C11—C12 | 118.2 (3) | C28—C29—C30 | 120.6 (4) |
O3—C11—C17 | 123.4 (3) | C28—C29—H29 | 119.4 |
C12—C11—C17 | 118.4 (3) | C30—C29—H29 | 120.0 |
C11—C12—C13 | 122.0 (3) | C29—C30—C31 | 120.6 (5) |
C11—C12—C14 | 119.1 (3) | C29—C30—H30 | 120.0 |
C13—C12—C14 | 118.8 (3) | C31—C30—H30 | 119.3 |
O5—C13—O6 | 118.8 (3) | C30—C31—C32 | 119.0 (4) |
O5—C13—C12 | 123.7 (3) | C30—C31—H31 | 120.4 |
O6—C13—C12 | 117.5 (3) | C32—C31—H31 | 120.6 |
C12—C14—C15 | 122.2 (3) | C27—C32—C31 | 120.4 (4) |
C12—C14—H14 | 118.6 | C27—C32—H32 | 120.1 |
C15—C14—H14 | 119.2 | C31—C32—H32 | 119.6 |
C14—C15—C16 | 118.5 (3) | N10—C33—C34 | 125.8 (3) |
C14—C15—H15 | 120.3 | N10—C33—H33 | 116.7 |
C16—C15—H15 | 121.2 | C34—C33—H33 | 117.6 |
C15—C16—C17 | 122.3 (3) | C33—C34—C35 | 116.6 (3) |
C15—C16—H16 | 119.2 | C33—C34—C40 | 124.8 (3) |
C17—C16—H16 | 118.5 | C35—C34—C40 | 118.6 (3) |
C11—C17—C16 | 119.3 (3) | C34—C35—C36 | 121.2 (3) |
C11—C17—C18 | 123.7 (3) | C34—C35—H35 | 119.2 |
C16—C17—C18 | 117.0 (3) | C36—C35—H35 | 119.6 |
N9—C18—C17 | 126.1 (3) | C35—C36—C37 | 120.1 (3) |
N9—C18—H18 | 116.7 | C35—C36—H36 | 120.2 |
C17—C18—H18 | 117.2 | C37—C36—H36 | 119.7 |
N9—C19—C20 | 115.2 (3) | C36—C37—C38 | 120.9 (3) |
N9—C19—C26 | 106.0 (3) | C36—C37—H37 | 119.9 |
N9—C19—H19 | 108.3 | C38—C37—H37 | 119.1 |
C20—C19—C26 | 111.0 (3) | C37—C38—C39 | 117.1 (3) |
C20—C19—H19 | 107.9 | C37—C38—C40 | 120.2 (3) |
C26—C19—H19 | 108.1 | C39—C38—C40 | 122.6 (3) |
N9—C19*—C20 | 104.3 (10) | O7—C39—O8 | 120.2 (3) |
N9—C19*—C26* | 98 (1) | O7—C39—C38 | 123.1 (3) |
N9—C19*—H19* | 114.5 | O8—C39—C38 | 116.6 (3) |
C20—C19*—C26* | 108 (1) | O4—C40—C34 | 121.9 (2) |
C20—C19*—H19* | 114.8 | O4—C40—C38 | 119.1 (2) |
C26*—C19*—H19* | 114.7 | C34—C40—C38 | 119.0 (3) |
C19—C20—C21 | 114.9 (3) | O41—C42—H42A | 109.9 |
C19—C20—C25 | 125.6 (3) | O41—C42—H42B | 110.4 |
C19*—C20—C21 | 145.4 (6) | O41—C42—H42C | 111.5 |
C19*—C20—C25 | 94.6 (6) | H42A—C42—H42B | 107.7 |
C21—C20—C25 | 119.5 (3) | H42A—C42—H42C | 108.6 |
C20—C21—C22 | 120.3 (4) | H42B—C42—H42C | 108.6 |
C20—C21—H21 | 119.3 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O3 | 0.97 (4) | 1.56 (4) | 2.476 (3) | 156 (3) |
O8—H8···O4 | 0.98 (3) | 1.63 (3) | 2.514 (3) | 148 (3) |
O41—H41···O5i | 0.96 (4) | 1.78 (2) | 2.732 (3) | 172 (3) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Crystal data top
[VO(C22H22N2O6)]·H2O | Z = 2 |
Mr = 495.37 | Dx = 1.487 Mg m−3 |
Triclinic, P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.508 (3) Å | Cell parameters from 25 reflections |
b = 11.728 (2) Å | θ = 14.9–15.0° |
c = 9.726 (2) Å | µ = 0.50 mm−1 |
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 scans | θmax = 30° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→14 |
Tmin = 0.860, Tmax = 0.915 | k = −16→16 |
6772 measured reflections | l = −13→13 |
6445 independent reflections | 3 standard reflections every 150 reflections |
5528 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | All 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 = 1.05 | Δρmax = 0.70 e Å−3 |
6445 reflections | Δρmin = −0.64 e Å−3 |
394 parameters | |
Crystal data top
[VO(C22H22N2O6)]·H2O | γ = 100.45 (2)° |
Mr = 495.37 | V = 1106.1 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.508 (3) Å | Mo Kα radiation |
b = 11.728 (2) Å | µ = 0.50 mm−1 |
c = 9.726 (2) Å | T = 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 = 0.915 | 3 standard reflections every 150 reflections |
6772 measured reflections | intensity decay: none |
6445 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 394 parameters |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.70 e Å−3 |
6445 reflections | Δρmin = −0.64 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
V1 | 0.93844 (2) | 0.23532 (2) | 0.43953 (2) | 0.02608 (8) | |
O2 | 1.0036 (1) | 0.3126 (1) | 0.3462 (1) | 0.0416 (3) | |
O3 | 1.0678 (1) | 0.2498 (1) | 0.6074 (1) | 0.0326 (2) | |
O4 | 0.9638 (1) | 0.0696 (1) | 0.3530 (1) | 0.0355 (2) | |
O5 | 1.4343 (1) | 0.2904 (1) | 0.8360 (2) | 0.0545 (4) | |
O6 | 1.2818 (2) | 0.1782 (1) | 0.6463 (2) | 0.0536 (4) | |
O7 | 1.1604 (2) | −0.1782 (1) | 0.1322 (2) | 0.0585 (4) | |
O8 | 1.1578 (2) | −0.0317 (2) | 0.3342 (2) | 0.0669 (5) | |
O33 | 0.5718 (2) | 0.1209 (2) | 0.9139 (3) | 0.0841 (7) | |
N9 | 0.8510 (1) | 0.3552 (1) | 0.5793 (1) | 0.0267 (2) | |
N10 | 0.7439 (1) | 0.1686 (1) | 0.3478 (1) | 0.0299 (2) | |
C11 | 1.1152 (1) | 0.3485 (1) | 0.7264 (2) | 0.0264 (2) | |
C12 | 1.2410 (1) | 0.3641 (1) | 0.8077 (2) | 0.0295 (3) | |
C13 | 1.3267 (2) | 0.2754 (2) | 0.7658 (2) | 0.0373 (3) | |
C14 | 1.2919 (2) | 0.4686 (2) | 0.9299 (2) | 0.0367 (3) | |
C15 | 1.2216 (2) | 0.5585 (2) | 0.9752 (2) | 0.0383 (3) | |
C16 | 1.0979 (2) | 0.5422 (1) | 0.8990 (2) | 0.0337 (3) | |
C17 | 1.0425 (1) | 0.4390 (1) | 0.7751 (2) | 0.0275 (2) | |
C18 | 0.9116 (1) | 0.4323 (1) | 0.7037 (2) | 0.0294 (3) | |
C19 | 0.7170 (1) | 0.3616 (1) | 0.5147 (2) | 0.0290 (3) | |
C20 | 0.7378 (2) | 0.4369 (2) | 0.4117 (2) | 0.0439 (4) | |
C21 | 0.6416 (2) | 0.4238 (2) | 0.6310 (2) | 0.0421 (4) | |
C22 | 0.6454 (1) | 0.2253 (1) | 0.4301 (2) | 0.0314 (3) | |
C23 | 0.5195 (2) | 0.2162 (2) | 0.3277 (2) | 0.0510 (5) | |
C24 | 0.6139 (2) | 0.1548 (2) | 0.5361 (3) | 0.0486 (4) | |
C25 | 0.7050 (1) | 0.0797 (2) | 0.2253 (2) | 0.0350 (3) | |
C26 | 0.7870 (1) | 0.0043 (1) | 0.1483 (2) | 0.0326 (3) | |
C27 | 0.7338 (2) | −0.0738 (2) | 0.0052 (2) | 0.0414 (4) | |
C28 | 0.8010 (2) | −0.1537 (2) | −0.0740 (2) | 0.0452 (4) | |
C29 | 0.9215 (2) | −0.1611 (2) | −0.0074 (2) | 0.0389 (3) | |
C30 | 0.9760 (2) | −0.0880 (1) | 0.1365 (2) | 0.0324 (3) | |
C31 | 1.1044 (2) | −0.1032 (2) | 0.1997 (2) | 0.0416 (4) | |
C32 | 0.9104 (1) | −0.0016 (1) | 0.2160 (2) | 0.0294 (3) | |
H6 | 1.209 (3) | 0.175 (3) | 0.623 (4) | 0.0900 (1)* | |
H8 | 1.100 (4) | 0.015 (3) | 0.369 (4) | 0.0985 (1)* | |
H14 | 1.374 (2) | 0.481 (2) | 0.981 (2) | 0.04735 (7)* | |
H15 | 1.260 (2) | 0.630 (2) | 1.060 (3) | 0.05258 (8)* | |
H16 | 1.047 (2) | 0.599 (2) | 0.924 (3) | 0.05054 (8)* | |
H18 | 0.872 (2) | 0.489 (2) | 0.753 (2) | 0.03272 (6)* | |
H20A | 0.795 (3) | 0.520 (2) | 0.464 (3) | 0.05827 (9)* | |
H20B | 0.774 (2) | 0.401 (2) | 0.337 (3) | 0.05209 (8)* | |
H20C | 0.657 (3) | 0.448 (2) | 0.366 (3) | 0.06366 (9)* | |
H21A | 0.641 (2) | 0.396 (2) | 0.710 (3) | 0.05008 (8)* | |
H21B | 0.685 (3) | 0.515 (3) | 0.667 (3) | 0.06448 (9)* | |
H21C | 0.551 (3) | 0.411 (2) | 0.581 (3) | 0.06145 (9)* | |
H23A | 0.470 (3) | 0.268 (2) | 0.377 (3) | 0.06091 (9)* | |
H23B | 0.473 (3) | 0.142 (2) | 0.297 (3) | 0.05343 (8)* | |
H23C | 0.537 (3) | 0.242 (2) | 0.244 (3) | 0.06223 (9)* | |
H24A | 0.541 (2) | 0.179 (2) | 0.583 (3) | 0.05292 (8)* | |
H24B | 0.682 (3) | 0.173 (3) | 0.610 (3) | 0.0667 (1)* | |
H24C | 0.587 (3) | 0.061 (3) | 0.482 (3) | 0.06793 (10)* | |
H25 | 0.615 (2) | 0.052 (2) | 0.185 (3) | 0.05270 (8)* | |
H27 | 0.661 (3) | −0.069 (3) | −0.032 (3) | 0.06791 (10)* | |
H28 | 0.768 (3) | −0.206 (3) | −0.173 (3) | 0.06824 (10)* | |
H29 | 0.969 (2) | −0.206 (2) | −0.055 (3) | 0.05341 (8)* | |
H33A | 0.532 (4) | 0.157 (3) | 0.881 (4) | 0.0904 (1)* | |
H33B | 0.645 (3) | 0.138 (3) | 0.897 (3) | 0.0748 (1)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
V1 | 0.0208 (1) | 0.0271 (1) | 0.0269 (1) | 0.00825 (8) | 0.00056 (8) | 0.00353 (8) |
O2 | 0.0388 (6) | 0.0450 (6) | 0.0425 (6) | 0.0103 (5) | 0.0119 (5) | 0.0146 (5) |
O3 | 0.0294 (5) | 0.0295 (5) | 0.0326 (5) | 0.0117 (4) | −0.0050 (4) | 0.0017 (4) |
O4 | 0.0314 (5) | 0.0338 (5) | 0.0334 (5) | 0.0158 (4) | −0.0059 (4) | −0.0013 (4) |
O5 | 0.0329 (6) | 0.0609 (8) | 0.0643 (9) | 0.0211 (6) | −0.0079 (6) | 0.0124 (7) |
O6 | 0.0424 (7) | 0.0525 (8) | 0.0564 (8) | 0.0265 (6) | −0.0051 (6) | −0.0003 (6) |
O7 | 0.0472 (7) | 0.0524 (8) | 0.0652 (9) | 0.0313 (6) | 0.0021 (6) | −0.0050 (7) |
O8 | 0.0520 (8) | 0.0667 (10) | 0.0601 (9) | 0.0397 (8) | −0.0188 (7) | −0.0161 (7) |
O33 | 0.0426 (9) | 0.077 (1) | 0.157 (2) | 0.0212 (9) | 0.016 (1) | 0.070 (1) |
N9 | 0.0229 (5) | 0.0283 (5) | 0.0293 (5) | 0.0104 (4) | 0.0021 (4) | 0.0081 (4) |
N10 | 0.0220 (5) | 0.0311 (6) | 0.0335 (6) | 0.0096 (4) | −0.0004 (4) | 0.0058 (5) |
C11 | 0.0247 (6) | 0.0266 (6) | 0.0271 (6) | 0.0060 (5) | 0.0009 (5) | 0.0088 (5) |
C12 | 0.0248 (6) | 0.0322 (7) | 0.0305 (6) | 0.0073 (5) | −0.0006 (5) | 0.0102 (5) |
C13 | 0.0281 (7) | 0.0423 (8) | 0.0428 (8) | 0.0137 (6) | 0.0015 (6) | 0.0142 (7) |
C14 | 0.0288 (7) | 0.0398 (8) | 0.0347 (7) | 0.0057 (6) | −0.0053 (6) | 0.0075 (6) |
C15 | 0.0371 (8) | 0.0347 (7) | 0.0329 (7) | 0.0058 (6) | −0.0044 (6) | 0.0014 (6) |
C16 | 0.0357 (7) | 0.0298 (7) | 0.0304 (7) | 0.0095 (6) | 0.0003 (5) | 0.0030 (5) |
C17 | 0.0257 (6) | 0.0287 (6) | 0.0262 (6) | 0.0076 (5) | 0.0011 (5) | 0.0066 (5) |
C18 | 0.0278 (6) | 0.0305 (6) | 0.0291 (6) | 0.0115 (5) | 0.0033 (5) | 0.0065 (5) |
C19 | 0.0254 (6) | 0.0323 (6) | 0.0309 (6) | 0.0127 (5) | 0.0015 (5) | 0.0101 (5) |
C20 | 0.0438 (9) | 0.0475 (10) | 0.0509 (10) | 0.0163 (8) | 0.0054 (8) | 0.0289 (8) |
C21 | 0.0340 (8) | 0.0512 (10) | 0.0403 (8) | 0.0234 (7) | 0.0060 (6) | 0.0061 (7) |
C22 | 0.0215 (6) | 0.0328 (7) | 0.0380 (7) | 0.0101 (5) | 0.0023 (5) | 0.0077 (6) |
C23 | 0.0281 (7) | 0.057 (1) | 0.054 (1) | 0.0193 (8) | −0.0094 (7) | −0.0017 (9) |
C24 | 0.0424 (9) | 0.0442 (10) | 0.069 (1) | 0.0128 (8) | 0.0233 (9) | 0.0269 (9) |
C25 | 0.0253 (6) | 0.0354 (7) | 0.0367 (7) | 0.0099 (5) | −0.0041 (5) | 0.0025 (6) |
C26 | 0.0286 (6) | 0.0308 (7) | 0.0316 (7) | 0.0093 (5) | −0.0027 (5) | 0.0018 (5) |
C27 | 0.0375 (8) | 0.0405 (8) | 0.0355 (8) | 0.0124 (7) | −0.0087 (6) | 0.0001 (6) |
C28 | 0.0498 (10) | 0.0411 (9) | 0.0335 (8) | 0.0145 (7) | −0.0053 (7) | −0.0019 (7) |
C29 | 0.0446 (9) | 0.0331 (7) | 0.0350 (7) | 0.0156 (6) | 0.0040 (6) | 0.0026 (6) |
C30 | 0.0320 (7) | 0.0271 (6) | 0.0354 (7) | 0.0111 (5) | 0.0029 (5) | 0.0048 (5) |
C31 | 0.0354 (8) | 0.0367 (8) | 0.0469 (9) | 0.0168 (6) | 0.0005 (7) | 0.0026 (7) |
C32 | 0.0276 (6) | 0.0256 (6) | 0.0305 (6) | 0.0078 (5) | −0.0003 (5) | 0.0037 (5) |
Geometric parameters (Å, º) top
V1—O2 | 1.588 (2) | C18—H18 | 0.89 (2) |
V1—O3 | 1.952 (1) | C19—C20 | 1.532 (3) |
V1—O4 | 1.950 (1) | C19—C21 | 1.531 (2) |
V1—N9 | 2.061 (1) | C19—C22 | 1.558 (2) |
V1—N10 | 2.047 (1) | C20—H20A | 1.00 (2) |
O3—C11 | 1.335 (2) | C20—H20B | 0.88 (3) |
O4—C32 | 1.334 (2) | C20—H20C | 0.96 (3) |
O5—C13 | 1.210 (2) | C21—H21A | 0.92 (3) |
O6—C13 | 1.324 (2) | C21—H21B | 1.02 (3) |
O6—H6 | 0.77 (4) | C21—H21C | 0.99 (3) |
O7—C31 | 1.213 (3) | C22—C23 | 1.534 (3) |
O8—C31 | 1.317 (2) | C22—C24 | 1.532 (3) |
O8—H8 | 0.91 (4) | C23—H23A | 0.93 (3) |
O33—H33A | 0.76 (4) | C23—H23B | 0.86 (2) |
O33—H33B | 0.81 (4) | C23—H23C | 0.97 (3) |
N9—C18 | 1.284 (2) | C24—H24A | 0.97 (3) |
N9—C19 | 1.503 (2) | C24—H24B | 0.90 (3) |
N10—C22 | 1.504 (2) | C24—H24C | 1.04 (3) |
N10—C25 | 1.289 (2) | C25—C26 | 1.449 (2) |
C11—C12 | 1.416 (2) | C25—H25 | 0.94 (2) |
C11—C17 | 1.415 (2) | C26—C27 | 1.401 (2) |
C12—C13 | 1.490 (2) | C26—C32 | 1.412 (2) |
C12—C14 | 1.393 (2) | C27—C28 | 1.375 (3) |
C14—C15 | 1.387 (3) | C27—H27 | 0.83 (3) |
C14—H14 | 0.91 (2) | C28—C29 | 1.388 (3) |
C15—C16 | 1.375 (2) | C28—H28 | 0.96 (2) |
C15—H15 | 0.96 (2) | C29—C30 | 1.393 (2) |
C16—C17 | 1.402 (2) | C29—H29 | 0.86 (3) |
C16—H16 | 0.92 (3) | C30—C31 | 1.485 (3) |
C17—C18 | 1.449 (2) | C30—C32 | 1.412 (2) |
| | | |
O2—V1—O3 | 109.44 (6) | C19—C20—H20C | 113 (2) |
O2—V1—O4 | 105.60 (6) | H20A—C20—H20B | 108 (2) |
O2—V1—N9 | 103.98 (6) | H20A—C20—H20C | 107 (2) |
O2—V1—N10 | 107.38 (6) | H20B—C20—H20C | 104 (2) |
O3—V1—O4 | 86.82 (5) | C19—C21—H21A | 115 (2) |
O3—V1—N9 | 88.75 (5) | C19—C21—H21B | 106 (2) |
O3—V1—N10 | 142.90 (6) | C19—C21—H21C | 107 (2) |
O4—V1—N9 | 149.87 (5) | H21A—C21—H21B | 109 (2) |
O4—V1—N10 | 87.72 (5) | H21A—C21—H21C | 110 (2) |
N9—V1—N10 | 78.08 (5) | H21B—C21—H21C | 110 (2) |
V1—O3—C11 | 127.1 (1) | N10—C22—C19 | 105.5 (1) |
V1—O4—C32 | 123.2 (1) | N10—C22—C23 | 112.2 (1) |
C13—O6—H6 | 108 (2) | N10—C22—C24 | 106.1 (1) |
C31—O8—H8 | 108 (2) | C19—C22—C23 | 111.6 (2) |
H33A—O33—H33B | 106 (4) | C19—C22—C24 | 111.1 (1) |
V1—N9—C18 | 123.4 (1) | C23—C22—C24 | 110.2 (2) |
V1—N9—C19 | 114.75 (8) | C22—C23—H23A | 110 (2) |
C18—N9—C19 | 121.1 (1) | C22—C23—H23B | 110 (2) |
V1—N10—C22 | 117.64 (8) | C22—C23—H23C | 113 (2) |
V1—N10—C25 | 122.1 (1) | H23A—C23—H23B | 109 (2) |
C22—N10—C25 | 120.2 (1) | H23A—C23—H23C | 106 (3) |
O3—C11—C12 | 119.9 (1) | H23B—C23—H23C | 109 (2) |
O3—C11—C17 | 121.7 (1) | C22—C24—H24A | 111 (2) |
C12—C11—C17 | 118.4 (1) | C22—C24—H24B | 111 (2) |
C11—C12—C13 | 123.0 (1) | C22—C24—H24C | 111 (2) |
C11—C12—C14 | 119.9 (1) | H24A—C24—H24B | 106 (2) |
C13—C12—C14 | 117.0 (1) | H24A—C24—H24C | 107 (2) |
O5—C13—O6 | 120.1 (2) | H24B—C24—H24C | 111 (3) |
O5—C13—C12 | 122.2 (1) | N10—C25—C26 | 125.4 (1) |
O6—C13—C12 | 117.7 (1) | N10—C25—H25 | 120 (1) |
C12—C14—C15 | 121.5 (1) | C26—C25—H25 | 113 (1) |
C12—C14—H14 | 121 (1) | C25—C26—C27 | 117.2 (1) |
C15—C14—H14 | 118 (1) | C25—C26—C32 | 122.8 (1) |
C14—C15—C16 | 118.9 (1) | C27—C26—C32 | 119.8 (1) |
C14—C15—H15 | 119 (2) | C26—C27—C28 | 121.6 (2) |
C16—C15—H15 | 122 (2) | C26—C27—H27 | 118 (2) |
C15—C16—C17 | 121.9 (2) | C28—C27—H27 | 120 (2) |
C15—C16—H16 | 122 (1) | C27—C28—C29 | 118.9 (1) |
C17—C16—H16 | 116 (1) | C27—C28—H28 | 123 (2) |
C11—C17—C16 | 119.5 (1) | C29—C28—H28 | 118 (2) |
C11—C17—C18 | 123.8 (1) | C28—C29—C30 | 121.3 (2) |
C16—C17—C18 | 116.8 (1) | C28—C29—H29 | 121 (2) |
N9—C18—C17 | 126.4 (1) | C30—C29—H29 | 117 (2) |
N9—C18—H18 | 119 (1) | C29—C30—C31 | 117.7 (2) |
C17—C18—H18 | 115 (1) | C29—C30—C32 | 120.0 (2) |
N9—C19—C20 | 106.7 (1) | C31—C30—C32 | 122.3 (1) |
N9—C19—C21 | 112.7 (1) | O7—C31—O8 | 119.8 (2) |
N9—C19—C22 | 104.8 (1) | O7—C31—C30 | 122.4 (1) |
C20—C19—C21 | 108.9 (2) | O8—C31—C30 | 117.8 (2) |
C20—C19—C22 | 112.0 (1) | O4—C32—C26 | 121.8 (1) |
C21—C19—C22 | 111.6 (1) | O4—C32—C30 | 119.9 (1) |
C19—C20—H20A | 112 (2) | C26—C32—C30 | 118.3 (1) |
C19—C20—H20B | 113 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O3 | 0.77 (4) | 1.87 (4) | 2.569 (2) | 152 (3) |
O8—H8···O4 | 0.91 (4) | 1.68 (4) | 2.535 (2) | 154 (3) |
O33—H33A···O5i | 0.76 (4) | 2.11 (4) | 2.886 (3) | 167 (3) |
O33—H33B···O7ii | 0.81 (4) | 2.08 (4) | 2.888 (3) | 175 (4) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | [VO(C30H22N2O6)(CH3OH)] | [VO(C22H22N2O6)]·H2O |
Mr | 605.50 | 495.37 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 298 | 298 |
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), 90 | 107.66 (2), 96.21 (2), 100.45 (2) |
V (Å3) | 2811.1 (7) | 1106.1 (5) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.41 | 0.50 |
Crystal size (mm) | 0.4 × 0.3 × 0.1 | 0.5 × 0.4 × 0.3 |
|
Data collection |
Diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | ψ scan (North et al., 1968) | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.901, 0.960 | 0.860, 0.915 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8471, 8202, 4703 | 6772, 6445, 5528 |
Rint | 0.014 | 0.085 |
(sin θ/λ)max (Å−1) | 0.703 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.167, 1.31 | 0.039, 0.116, 1.05 |
No. of reflections | 8202 | 6445 |
No. of parameters | 397 | 394 |
No. of restraints | ? | ? |
H-atom treatment | H atoms: see text | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.50, −0.44 | 0.70, −0.64 |
Selected geometric parameters (Å, º) for (I) topV1—O2 | 1.584 (3) | V1—O41 | 2.368 (3) |
V1—O3 | 1.969 (2) | V1—N9 | 2.045 (3) |
V1—O4 | 1.948 (2) | V1—N10 | 2.048 (2) |
| | | |
O2—V1—O41 | 178.0 (1) | O41—V1—N9 | 80.35 (10) |
O3—V1—O41 | 78.59 (10) | O41—V1—N10 | 79.71 (10) |
O4—V1—O41 | 80.10 (9) | V1—O41—C42 | 126.4 (3) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O3 | 0.97 (4) | 1.56 (4) | 2.476 (3) | 156 (3) |
O8—H8···O4 | 0.98 (3) | 1.63 (3) | 2.514 (3) | 148 (3) |
O41—H41···O5i | 0.96 (4) | 1.78 (2) | 2.732 (3) | 172 (3) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Selected bond lengths (Å) for (II) topV1—O2 | 1.588 (2) | V1—N9 | 2.061 (1) |
V1—O3 | 1.952 (1) | V1—N10 | 2.047 (1) |
V1—O4 | 1.950 (1) | | |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O3 | 0.77 (4) | 1.87 (4) | 2.569 (2) | 152 (3) |
O8—H8···O4 | 0.91 (4) | 1.68 (4) | 2.535 (2) | 154 (3) |
O33—H33A···O5i | 0.76 (4) | 2.11 (4) | 2.886 (3) | 167 (3) |
O33—H33B···O7ii | 0.81 (4) | 2.08 (4) | 2.888 (3) | 175 (4) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1. |
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].