Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002295/cv6084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002295/cv6084Isup2.hkl |
CCDC reference: 182571
A dark-brown plate crystal of (I) was obtained by slow evapolation from a propanol solution of a mixture of 8-hydroxyquinoline and VOSO4 (8:1).
All H atoms, except those attached to C3P, were checked their presence in difference Fourier maps, and after that they were fixed at ideal positions and included in the refinement.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Displacement ellipsoids for non-H atoms correspond to 50% probability. |
C21H19N2O4V | Z = 2 |
Mr = 414.33 | F(000) = 422.0 |
Triclinic, P1 | Dx = 1.442 Mg m−3 |
a = 9.639 (3) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 12.751 (3) Å | Cell parameters from 25 reflections |
c = 9.044 (3) Å | θ = 14.7–15.0° |
α = 95.76 (2)° | µ = 0.55 mm−1 |
β = 110.97 (2)° | T = 296 K |
γ = 108.63 (2)° | Hexagonal, dark brown |
V = 954.1 (5) Å3 | 0.20 × 0.20 × 0.07 mm |
Rigaku AFC-5R diffractometer | Rint = 0.018 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→12 |
Tmin = 0.896, Tmax = 0.962 | k = −16→15 |
4645 measured reflections | l = −11→10 |
4391 independent reflections | 3 standard reflections every 150 reflections |
2952 reflections with I > 2σ(I) | intensity decay: 0.6% |
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.176 | (Δ/σ)max = −0.002 |
S = 1.14 | Δρmax = 0.64 e Å−3 |
4389 reflections | Δρmin = −0.43 e Å−3 |
253 parameters |
C21H19N2O4V | γ = 108.63 (2)° |
Mr = 414.33 | V = 954.1 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.639 (3) Å | Mo Kα radiation |
b = 12.751 (3) Å | µ = 0.55 mm−1 |
c = 9.044 (3) Å | T = 296 K |
α = 95.76 (2)° | 0.20 × 0.20 × 0.07 mm |
β = 110.97 (2)° |
Rigaku AFC-5R diffractometer | 2952 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.018 |
Tmin = 0.896, Tmax = 0.962 | 3 standard reflections every 150 reflections |
4645 measured reflections | intensity decay: 0.6% |
4391 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 253 parameters |
wR(F2) = 0.176 | H-atom parameters not refined |
S = 1.14 | Δρmax = 0.64 e Å−3 |
4389 reflections | Δρmin = −0.43 e Å−3 |
Refinement. Refinement using reflections with F2 > -10.0 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). |
x | y | z | Uiso*/Ueq | ||
V(1) | 0.63027 (6) | 0.26595 (4) | 0.03618 (7) | 0.0384 (2) | |
O(1A) | 0.7176 (3) | 0.1585 (2) | 0.1250 (3) | 0.0420 (5) | |
O(1B) | 0.5153 (3) | 0.3619 (2) | 0.0301 (3) | 0.0424 (5) | |
O(1V) | 0.7766 (3) | 0.3553 (2) | 0.0133 (3) | 0.0513 (6) | |
O(2V) | 0.5153 (3) | 0.1735 (2) | −0.1621 (3) | 0.0477 (5) | |
N(1A) | 0.7414 (3) | 0.3407 (2) | 0.3017 (3) | 0.0414 (6) | |
N(1B) | 0.4235 (3) | 0.1651 (2) | 0.1012 (3) | 0.0376 (5) | |
C(1A) | 0.7531 (5) | 0.4364 (3) | 0.3848 (5) | 0.0537 (9) | |
C(1B) | 0.3814 (4) | 0.0644 (3) | 0.1350 (4) | 0.0447 (7) | |
C(1P) | 0.5377 (6) | 0.1806 (4) | −0.3083 (5) | 0.069 (1) | |
C(2A) | 0.8324 (6) | 0.4703 (3) | 0.5566 (5) | 0.067 (1) | |
C(2B) | 0.2457 (5) | 0.0203 (3) | 0.1678 (5) | 0.0570 (9) | |
C(2P) | 0.451 (1) | 0.242 (1) | −0.4067 (9) | 0.172 (4) | |
C(3A) | 0.8964 (5) | 0.4039 (4) | 0.6399 (5) | 0.064 (1) | |
C(3B) | 0.1516 (4) | 0.0814 (3) | 0.1641 (5) | 0.0544 (9) | |
C(3P) | 0.359 (1) | 0.290 (1) | −0.3968 (10) | 0.198 (5) | |
C(4A) | 0.8850 (4) | 0.2985 (3) | 0.5575 (4) | 0.0528 (8) | |
C(4B) | 0.1900 (4) | 0.1885 (3) | 0.1256 (4) | 0.0420 (7) | |
C(5A) | 0.9409 (5) | 0.2195 (4) | 0.6288 (5) | 0.067 (1) | |
C(5B) | 0.1016 (4) | 0.2598 (3) | 0.1144 (4) | 0.0485 (8) | |
C(6A) | 0.9165 (6) | 0.1193 (4) | 0.5320 (5) | 0.067 (1) | |
C(6B) | 0.1538 (4) | 0.3620 (3) | 0.0769 (4) | 0.0474 (8) | |
C(7A) | 0.8397 (5) | 0.0938 (3) | 0.3601 (5) | 0.0546 (9) | |
C(7B) | 0.2949 (4) | 0.4008 (3) | 0.0493 (4) | 0.0432 (7) | |
C(8A) | 0.7871 (4) | 0.1714 (3) | 0.2853 (4) | 0.0402 (7) | |
C(8B) | 0.3822 (4) | 0.3333 (2) | 0.0578 (4) | 0.0369 (6) | |
C(9A) | 0.8063 (4) | 0.2728 (3) | 0.3860 (4) | 0.0410 (7) | |
C(9B) | 0.3295 (4) | 0.2263 (2) | 0.0956 (4) | 0.0355 (6) | |
H(1A) | 0.7048 | 0.4853 | 0.3281 | 0.0558* | |
H(1B) | 0.4461 | 0.0213 | 0.1407 | 0.0455* | |
H(1PA) | 0.6511 | 0.2184 | −0.2795 | 0.0847* | |
H(1PB) | 0.5039 | 0.1047 | −0.3709 | 0.0847* | |
H(2A) | 0.8415 | 0.5436 | 0.6155 | 0.0701* | |
H(2B) | 0.2137 | −0.0528 | 0.1934 | 0.0539* | |
H(2PA) | 0.5359 | 0.2993 | −0.4211 | 0.2038* | |
H(2PB) | 0.3878 | 0.1858 | −0.5108 | 0.2038* | |
H(3A) | 0.9494 | 0.4262 | 0.7607 | 0.0667* | |
H(3B) | 0.0580 | 0.0490 | 0.1844 | 0.0531* | |
H(5A) | 0.9925 | 0.2326 | 0.7458 | 0.0648* | |
H(5B) | 0.0051 | 0.2354 | 0.1318 | 0.0449* | |
H(6A) | 0.9560 | 0.0688 | 0.5849 | 0.0700* | |
H(6B) | 0.0910 | 0.4085 | 0.0695 | 0.0487* | |
H(7A) | 0.8238 | 0.0225 | 0.2957 | 0.0564* | |
H(7B) | 0.3287 | 0.4746 | 0.0263 | 0.0413* |
U11 | U22 | U33 | U12 | U13 | U23 | |
V(1) | 0.0401 (3) | 0.0384 (3) | 0.0454 (3) | 0.0196 (2) | 0.0222 (2) | 0.0141 (2) |
O(1A) | 0.048 (1) | 0.042 (1) | 0.042 (1) | 0.0258 (10) | 0.018 (1) | 0.0094 (9) |
O(1B) | 0.041 (1) | 0.037 (1) | 0.063 (1) | 0.0205 (9) | 0.029 (1) | 0.022 (1) |
O(1V) | 0.044 (1) | 0.053 (1) | 0.070 (2) | 0.021 (1) | 0.034 (1) | 0.026 (1) |
O(2V) | 0.056 (1) | 0.051 (1) | 0.042 (1) | 0.027 (1) | 0.020 (1) | 0.012 (1) |
N(1A) | 0.040 (1) | 0.034 (1) | 0.047 (2) | 0.013 (1) | 0.018 (1) | 0.005 (1) |
N(1B) | 0.041 (1) | 0.033 (1) | 0.041 (1) | 0.015 (1) | 0.018 (1) | 0.009 (1) |
C(1A) | 0.058 (2) | 0.040 (2) | 0.061 (2) | 0.018 (2) | 0.024 (2) | 0.004 (2) |
C(1B) | 0.053 (2) | 0.035 (2) | 0.049 (2) | 0.016 (1) | 0.023 (2) | 0.012 (1) |
C(1P) | 0.095 (3) | 0.084 (3) | 0.054 (2) | 0.049 (3) | 0.043 (2) | 0.025 (2) |
C(2A) | 0.078 (3) | 0.052 (2) | 0.062 (2) | 0.019 (2) | 0.031 (2) | −0.006 (2) |
C(2B) | 0.059 (2) | 0.045 (2) | 0.069 (2) | 0.014 (2) | 0.031 (2) | 0.024 (2) |
C(2P) | 0.187 (8) | 0.34 (1) | 0.100 (5) | 0.179 (9) | 0.090 (6) | 0.146 (7) |
C(3A) | 0.067 (2) | 0.065 (2) | 0.046 (2) | 0.013 (2) | 0.022 (2) | 0.000 (2) |
C(3B) | 0.048 (2) | 0.052 (2) | 0.063 (2) | 0.008 (2) | 0.031 (2) | 0.019 (2) |
C(3P) | 0.30 (1) | 0.31 (1) | 0.098 (5) | 0.27 (1) | 0.070 (7) | 0.074 (7) |
C(4A) | 0.049 (2) | 0.058 (2) | 0.045 (2) | 0.013 (2) | 0.019 (2) | 0.007 (2) |
C(4B) | 0.037 (2) | 0.046 (2) | 0.039 (2) | 0.013 (1) | 0.016 (1) | 0.007 (1) |
C(5A) | 0.071 (3) | 0.083 (3) | 0.049 (2) | 0.034 (2) | 0.021 (2) | 0.027 (2) |
C(5B) | 0.039 (2) | 0.063 (2) | 0.051 (2) | 0.022 (2) | 0.025 (2) | 0.012 (2) |
C(6A) | 0.079 (3) | 0.078 (3) | 0.060 (2) | 0.045 (2) | 0.026 (2) | 0.036 (2) |
C(6B) | 0.044 (2) | 0.058 (2) | 0.046 (2) | 0.030 (2) | 0.017 (1) | 0.007 (1) |
C(7A) | 0.064 (2) | 0.056 (2) | 0.056 (2) | 0.034 (2) | 0.026 (2) | 0.022 (2) |
C(7B) | 0.048 (2) | 0.041 (2) | 0.048 (2) | 0.025 (1) | 0.021 (1) | 0.013 (1) |
C(8A) | 0.039 (2) | 0.044 (2) | 0.044 (2) | 0.019 (1) | 0.020 (1) | 0.013 (1) |
C(8B) | 0.039 (2) | 0.034 (1) | 0.039 (2) | 0.015 (1) | 0.018 (1) | 0.009 (1) |
C(9A) | 0.038 (2) | 0.038 (2) | 0.044 (2) | 0.010 (1) | 0.018 (1) | 0.008 (1) |
C(9B) | 0.036 (1) | 0.036 (1) | 0.033 (1) | 0.013 (1) | 0.014 (1) | 0.007 (1) |
V(1)—O(1A) | 1.924 (3) | C(2P)—H(2PA) | 0.966 |
V(1)—O(1B) | 1.888 (3) | C(2P)—H(2PB) | 0.973 |
V(1)—O(1V) | 1.600 (3) | C(3A)—C(4A) | 1.421 (7) |
V(1)—O(2V) | 1.775 (2) | C(3A)—H(3A) | 0.990 |
V(1)—N(1A) | 2.207 (3) | C(3B)—C(4B) | 1.409 (5) |
V(1)—N(1B) | 2.307 (3) | C(3B)—H(3B) | 0.956 |
O(1A)—C(8A) | 1.328 (4) | C(4A)—C(5A) | 1.396 (7) |
O(1B)—C(8B) | 1.338 (5) | C(4A)—C(9A) | 1.409 (5) |
O(2V)—C(1P) | 1.420 (6) | C(4B)—C(5B) | 1.419 (6) |
N(1A)—C(1A) | 1.317 (5) | C(4B)—C(9B) | 1.410 (5) |
N(1A)—C(9A) | 1.363 (5) | C(5A)—C(6A) | 1.375 (7) |
N(1B)—C(1B) | 1.319 (4) | C(5A)—H(5A) | 0.964 |
N(1B)—C(9B) | 1.364 (5) | C(5B)—C(6B) | 1.363 (6) |
C(1A)—C(2A) | 1.411 (6) | C(5B)—H(5B) | 0.958 |
C(1A)—H(1A) | 0.973 | C(6A)—C(7A) | 1.411 (6) |
C(1B)—C(2B) | 1.399 (6) | C(6A)—H(6A) | 0.936 |
C(1B)—H(1B) | 0.947 | C(6B)—C(7B) | 1.412 (6) |
C(1P)—C(2P) | 1.46 (1) | C(6B)—H(6B) | 0.965 |
C(1P)—H(1PA) | 0.965 | C(7A)—C(8A) | 1.379 (6) |
C(1P)—H(1PB) | 0.960 | C(7A)—H(7A) | 0.964 |
C(2A)—C(3A) | 1.339 (7) | C(7B)—C(8B) | 1.373 (6) |
C(2A)—H(2A) | 0.990 | C(7B)—H(7B) | 0.963 |
C(2B)—C(3B) | 1.365 (7) | C(8A)—C(9A) | 1.424 (5) |
C(2B)—H(2B) | 0.964 | C(8B)—C(9B) | 1.418 (4) |
C(2P)—C(3P) | 1.26 (2) | ||
O(1A)···C(1B)i | 3.137 (4) | O(1V)···C(7B)iii | 3.451 (5) |
O(1A)···C(2B)i | 3.509 (6) | O(1V)···C(5B)ii | 3.570 (5) |
O(1A)···C(5B)ii | 3.551 (5) | O(2V)···C(1B)i | 3.488 (5) |
O(1B)···C(7B)iii | 3.295 (4) | C(1A)···C(3A)iv | 3.442 (6) |
O(1V)···C(6B)ii | 3.443 (5) | C(3B)···C(3B)v | 3.215 (6) |
O(1A)—V(1)—O(1B) | 153.0 (1) | C(3P)—C(2P)—H(2PA) | 104.8 |
O(1A)—V(1)—O(1V) | 103.0 (1) | C(3P)—C(2P)—H(2PB) | 103.4 |
O(1A)—V(1)—O(2V) | 93.7 (1) | H(2PA)—C(2P)—H(2PB) | 106.3 |
O(1A)—V(1)—N(1A) | 76.9 (1) | C(2A)—C(3A)—C(4A) | 120.9 (4) |
O(1A)—V(1)—N(1B) | 82.1 (1) | C(2A)—C(3A)—H(3A) | 120.4 |
O(1B)—V(1)—O(1V) | 96.2 (1) | C(4A)—C(3A)—H(3A) | 118.7 |
O(1B)—V(1)—O(2V) | 100.6 (1) | C(2B)—C(3B)—C(4B) | 120.1 (4) |
O(1B)—V(1)—N(1A) | 83.8 (1) | C(2B)—C(3B)—H(3B) | 118.8 |
O(1B)—V(1)—N(1B) | 76.2 (1) | C(4B)—C(3B)—H(3B) | 121.0 |
O(1V)—V(1)—O(2V) | 102.1 (1) | C(3A)—C(4A)—C(5A) | 126.9 (4) |
O(1V)—V(1)—N(1A) | 91.7 (1) | C(3A)—C(4A)—C(9A) | 114.9 (4) |
O(1V)—V(1)—N(1B) | 169.6 (1) | C(5A)—C(4A)—C(9A) | 118.1 (4) |
O(2V)—V(1)—N(1A) | 164.8 (1) | C(3B)—C(4B)—C(5B) | 126.1 (4) |
O(2V)—V(1)—N(1B) | 86.4 (1) | C(3B)—C(4B)—C(9B) | 115.8 (4) |
N(1A)—V(1)—N(1B) | 80.52 (10) | C(5B)—C(4B)—C(9B) | 118.1 (3) |
V(1)—O(1A)—C(8A) | 120.8 (2) | C(4A)—C(5A)—C(6A) | 119.9 (4) |
V(1)—O(1B)—C(8B) | 123.0 (2) | C(4A)—C(5A)—H(5A) | 120.9 |
V(1)—O(2V)—C(1P) | 129.7 (2) | C(6A)—C(5A)—H(5A) | 119.2 |
V(1)—N(1A)—C(1A) | 130.5 (3) | C(4B)—C(5B)—C(6B) | 119.7 (4) |
V(1)—N(1A)—C(9A) | 111.2 (2) | C(4B)—C(5B)—H(5B) | 119.8 |
C(1A)—N(1A)—C(9A) | 118.3 (3) | C(6B)—C(5B)—H(5B) | 120.5 |
V(1)—N(1B)—C(1B) | 132.9 (3) | C(5A)—C(6A)—C(7A) | 122.2 (5) |
V(1)—N(1B)—C(9B) | 108.5 (2) | C(5A)—C(6A)—H(6A) | 117.0 |
C(1B)—N(1B)—C(9B) | 118.5 (3) | C(7A)—C(6A)—H(6A) | 120.8 |
N(1A)—C(1A)—C(2A) | 121.7 (4) | C(5B)—C(6B)—C(7B) | 122.3 (4) |
N(1A)—C(1A)—H(1A) | 120.1 | C(5B)—C(6B)—H(6B) | 117.9 |
C(2A)—C(1A)—H(1A) | 118.1 | C(7B)—C(6B)—H(6B) | 119.9 |
N(1B)—C(1B)—C(2B) | 121.9 (4) | C(6A)—C(7A)—C(8A) | 119.5 (4) |
N(1B)—C(1B)—H(1B) | 119.6 | C(6A)—C(7A)—H(7A) | 120.1 |
C(2B)—C(1B)—H(1B) | 118.5 | C(8A)—C(7A)—H(7A) | 120.4 |
O(2V)—C(1P)—C(2P) | 113.4 (6) | C(6B)—C(7B)—C(8B) | 119.5 (3) |
O(2V)—C(1P)—H(1PA) | 108.3 | C(6B)—C(7B)—H(7B) | 119.3 |
O(2V)—C(1P)—H(1PB) | 108.6 | C(8B)—C(7B)—H(7B) | 121.3 |
C(2P)—C(1P)—H(1PA) | 109.2 | O(1A)—C(8A)—C(7A) | 125.0 (3) |
C(2P)—C(1P)—H(1PB) | 109.8 | O(1A)—C(8A)—C(9A) | 116.8 (3) |
H(1PA)—C(1P)—H(1PB) | 107.4 | C(7A)—C(8A)—C(9A) | 118.2 (3) |
C(1A)—C(2A)—C(3A) | 120.1 (4) | O(1B)—C(8B)—C(7B) | 123.6 (3) |
C(1A)—C(2A)—H(2A) | 119.8 | O(1B)—C(8B)—C(9B) | 117.2 (3) |
C(3A)—C(2A)—H(2A) | 120.0 | C(7B)—C(8B)—C(9B) | 119.2 (3) |
C(1B)—C(2B)—C(3B) | 120.1 (4) | N(1A)—C(9A)—C(4A) | 124.0 (3) |
C(1B)—C(2B)—H(2B) | 123.0 | N(1A)—C(9A)—C(8A) | 114.0 (3) |
C(3B)—C(2B)—H(2B) | 117.0 | C(4A)—C(9A)—C(8A) | 122.0 (3) |
C(1P)—C(2P)—C(3P) | 136.3 (9) | N(1B)—C(9B)—C(4B) | 123.6 (3) |
C(1P)—C(2P)—H(2PA) | 102.0 | N(1B)—C(9B)—C(8B) | 115.1 (3) |
C(1P)—C(2P)—H(2PB) | 101.4 | C(4B)—C(9B)—C(8B) | 121.3 (3) |
V(1)—O(1A)—C(8A)—C(7A) | 173.7 (3) | N(1B)—C(9B)—C(8B)—C(7B) | 179.9 (3) |
V(1)—O(1A)—C(8A)—C(9A) | −5.5 (4) | C(1A)—N(1A)—C(9A)—C(4A) | 0.2 (5) |
V(1)—O(1B)—C(8B)—C(7B) | −178.1 (2) | C(1A)—N(1A)—C(9A)—C(8A) | 179.9 (3) |
V(1)—O(1B)—C(8B)—C(9B) | 1.0 (3) | C(1A)—C(2A)—C(3A)—C(4A) | −0.4 (8) |
V(1)—O(2V)—C(1P)—C(2P) | −91.6 (5) | C(1A)—C(2A)—C(3A)—H(3A) | −178.2 |
V(1)—O(2V)—C(1P)—H(1PA) | 29.7 | C(1B)—N(1B)—C(9B)—C(4B) | 0.7 (4) |
V(1)—O(2V)—C(1P)—H(1PB) | 146.1 | C(1B)—N(1B)—C(9B)—C(8B) | −179.7 (3) |
V(1)—N(1A)—C(1A)—C(2A) | −178.9 (3) | C(1B)—C(2B)—C(3B)—C(4B) | 0.6 (5) |
V(1)—N(1A)—C(1A)—H(1A) | 2.1 | C(1B)—C(2B)—C(3B)—H(3B) | 178.6 |
V(1)—N(1A)—C(9A)—C(4A) | −179.9 (3) | C(2A)—C(1A)—N(1A)—C(9A) | 1.0 (6) |
V(1)—N(1A)—C(9A)—C(8A) | −0.2 (4) | C(2A)—C(3A)—C(4A)—C(5A) | −177.6 (5) |
V(1)—N(1B)—C(1B)—C(2B) | −178.6 (2) | C(2A)—C(3A)—C(4A)—C(9A) | 1.4 (7) |
V(1)—N(1B)—C(1B)—H(1B) | 3.4 | C(2B)—C(1B)—N(1B)—C(9B) | −1.2 (4) |
V(1)—N(1B)—C(9B)—C(4B) | 178.7 (2) | C(2B)—C(3B)—C(4B)—C(5B) | 178.7 (3) |
V(1)—N(1B)—C(9B)—C(8B) | −1.7 (3) | C(2B)—C(3B)—C(4B)—C(9B) | −1.1 (5) |
O(1A)—V(1)—O(1B)—C(8B) | −38.7 (3) | C(3A)—C(2A)—C(1A)—H(1A) | 178.0 |
O(1A)—V(1)—O(2V)—C(1P) | −108.7 (4) | C(3A)—C(4A)—C(5A)—C(6A) | 178.2 (5) |
O(1A)—V(1)—N(1A)—C(1A) | 178.0 (4) | C(3A)—C(4A)—C(5A)—H(5A) | 0.8 |
O(1A)—V(1)—N(1A)—C(9A) | −1.9 (2) | C(3A)—C(4A)—C(9A)—C(8A) | 179.0 (4) |
O(1A)—V(1)—N(1B)—C(1B) | −16.9 (3) | C(3B)—C(2B)—C(1B)—H(1B) | 178.6 |
O(1A)—V(1)—N(1B)—C(9B) | 165.6 (2) | C(3B)—C(4B)—C(5B)—C(6B) | 179.6 (3) |
O(1A)—C(8A)—C(7A)—C(6A) | 178.0 (4) | C(3B)—C(4B)—C(5B)—H(5B) | −1.2 |
O(1A)—C(8A)—C(7A)—H(7A) | −2.3 | C(3B)—C(4B)—C(9B)—C(8B) | −179.1 (3) |
O(1A)—C(8A)—C(9A)—N(1A) | 3.4 (5) | C(3P)—C(2P)—C(1P)—H(1PA) | −121.8 |
O(1A)—C(8A)—C(9A)—C(4A) | −177.0 (3) | C(3P)—C(2P)—C(1P)—H(1PB) | 120.7 |
O(1B)—V(1)—O(1A)—C(8A) | −41.6 (3) | C(4A)—C(3A)—C(2A)—H(2A) | −179.8 |
O(1B)—V(1)—O(2V)—C(1P) | 94.2 (4) | C(4A)—C(5A)—C(6A)—C(7A) | 1.7 (8) |
O(1B)—V(1)—N(1A)—C(1A) | −21.0 (3) | C(4A)—C(5A)—C(6A)—H(6A) | 180.0 |
O(1B)—V(1)—N(1A)—C(9A) | 159.1 (2) | C(4A)—C(9A)—C(8A)—C(7A) | 3.8 (5) |
O(1B)—V(1)—N(1B)—C(1B) | 179.3 (3) | C(4B)—C(3B)—C(2B)—H(2B) | −179.3 |
O(1B)—V(1)—N(1B)—C(9B) | 1.7 (2) | C(4B)—C(5B)—C(6B)—C(7B) | −0.4 (5) |
O(1B)—C(8B)—C(7B)—C(6B) | 178.5 (3) | C(4B)—C(5B)—C(6B)—H(6B) | 179.7 |
O(1B)—C(8B)—C(7B)—H(7B) | −2.3 | C(4B)—C(9B)—C(8B)—C(7B) | −0.4 (4) |
O(1B)—C(8B)—C(9B)—N(1B) | 0.8 (4) | C(5A)—C(4A)—C(3A)—H(3A) | 0.3 |
O(1B)—C(8B)—C(9B)—C(4B) | −179.6 (2) | C(5A)—C(4A)—C(9A)—C(8A) | −1.9 (6) |
O(1V)—V(1)—O(1A)—C(8A) | 92.7 (3) | C(5A)—C(6A)—C(7A)—C(8A) | 0.2 (7) |
O(1V)—V(1)—O(1B)—C(8B) | −174.3 (2) | C(5A)—C(6A)—C(7A)—H(7A) | −179.6 |
O(1V)—V(1)—O(2V)—C(1P) | −4.6 (4) | C(5B)—C(4B)—C(3B)—H(3B) | 0.9 |
O(1V)—V(1)—N(1A)—C(1A) | 75.1 (4) | C(5B)—C(4B)—C(9B)—C(8B) | 1.0 (4) |
O(1V)—V(1)—N(1A)—C(9A) | −104.8 (3) | C(5B)—C(6B)—C(7B)—C(8B) | 1.0 (5) |
O(1V)—V(1)—N(1B)—C(1B) | −137.0 (6) | C(5B)—C(6B)—C(7B)—H(7B) | −178.2 |
O(1V)—V(1)—N(1B)—C(9B) | 45.4 (7) | C(6A)—C(5A)—C(4A)—C(9A) | −0.8 (7) |
O(2V)—V(1)—O(1A)—C(8A) | −163.9 (3) | C(6A)—C(7A)—C(8A)—C(9A) | −2.8 (6) |
O(2V)—V(1)—O(1B)—C(8B) | 82.1 (2) | C(6B)—C(5B)—C(4B)—C(9B) | −0.6 (4) |
O(2V)—V(1)—N(1A)—C(1A) | −128.9 (5) | C(6B)—C(7B)—C(8B)—C(9B) | −0.5 (4) |
O(2V)—V(1)—N(1A)—C(9A) | 51.2 (6) | C(7A)—C(6A)—C(5A)—H(5A) | 179.1 |
O(2V)—V(1)—N(1B)—C(1B) | 77.4 (3) | C(7B)—C(6B)—C(5B)—H(5B) | −179.6 |
O(2V)—V(1)—N(1B)—C(9B) | −100.2 (2) | C(8A)—C(7A)—C(6A)—H(6A) | −178.0 |
O(2V)—C(1P)—C(2P)—C(3P) | 0 (1) | C(8B)—C(7B)—C(6B)—H(6B) | −179.1 |
O(2V)—C(1P)—C(2P)—H(2PA) | 125.9 | C(9A)—N(1A)—C(1A)—H(1A) | −177.9 |
O(2V)—C(1P)—C(2P)—H(2PB) | −124.5 | C(9A)—C(4A)—C(3A)—H(3A) | 179.3 |
N(1A)—V(1)—O(1A)—C(8A) | 4.0 (2) | C(9A)—C(4A)—C(5A)—H(5A) | −178.1 |
N(1A)—V(1)—O(1B)—C(8B) | −83.2 (2) | C(9A)—C(8A)—C(7A)—H(7A) | 176.9 |
N(1A)—V(1)—O(2V)—C(1P) | −160.0 (5) | C(9B)—N(1B)—C(1B)—H(1B) | −179.2 |
N(1A)—V(1)—N(1B)—C(1B) | −94.8 (3) | C(9B)—C(4B)—C(3B)—H(3B) | −179.0 |
N(1A)—V(1)—N(1B)—C(9B) | 87.6 (2) | C(9B)—C(4B)—C(5B)—H(5B) | 178.6 |
N(1A)—C(1A)—C(2A)—C(3A) | −0.9 (7) | C(9B)—C(8B)—C(7B)—H(7B) | 178.7 |
N(1A)—C(1A)—C(2A)—H(2A) | 178.5 | H(1A)—C(1A)—C(2A)—H(2A) | −2.5 |
N(1A)—C(9A)—C(4A)—C(3A) | −1.4 (6) | H(1B)—C(1B)—C(2B)—H(2B) | −1.5 |
N(1A)—C(9A)—C(4A)—C(5A) | 177.7 (4) | H(1PA)—C(1P)—C(2P)—H(2PA) | 5.0 |
N(1A)—C(9A)—C(8A)—C(7A) | −175.9 (3) | H(1PA)—C(1P)—C(2P)—H(2PB) | 114.6 |
N(1B)—V(1)—O(1A)—C(8A) | −78.1 (2) | H(1PB)—C(1P)—C(2P)—H(2PA) | −112.5 |
N(1B)—V(1)—O(1B)—C(8B) | −1.5 (2) | H(1PB)—C(1P)—C(2P)—H(2PB) | −2.9 |
N(1B)—V(1)—O(2V)—C(1P) | 169.4 (4) | H(2A)—C(2A)—C(3A)—H(3A) | 2.4 |
N(1B)—V(1)—N(1A)—C(1A) | −98.0 (4) | H(2B)—C(2B)—C(3B)—H(3B) | −1.3 |
N(1B)—V(1)—N(1A)—C(9A) | 82.1 (2) | H(5A)—C(5A)—C(6A)—H(6A) | −2.6 |
N(1B)—C(1B)—C(2B)—C(3B) | 0.6 (5) | H(5B)—C(5B)—C(6B)—H(6B) | 0.4 |
N(1B)—C(1B)—C(2B)—H(2B) | −179.5 | H(6A)—C(6A)—C(7A)—H(7A) | 2.2 |
N(1B)—C(9B)—C(4B)—C(3B) | 0.4 (4) | H(6B)—C(6B)—C(7B)—H(7B) | 1.7 |
N(1B)—C(9B)—C(4B)—C(5B) | −179.4 (3) | H(6B)—C(6B)—C(7B)—H(7B) | 1.7 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z+1; (v) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H19N2O4V |
Mr | 414.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.639 (3), 12.751 (3), 9.044 (3) |
α, β, γ (°) | 95.76 (2), 110.97 (2), 108.63 (2) |
V (Å3) | 954.1 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.20 × 0.20 × 0.07 |
Data collection | |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.896, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4645, 4391, 2952 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.176, 1.14 |
No. of reflections | 4389 |
No. of parameters | 253 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.64, −0.43 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999), SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.
V(1)—O(1A) | 1.924 (3) | V(1)—N(1B) | 2.307 (3) |
V(1)—O(1B) | 1.888 (3) | O(1A)—C(8A) | 1.328 (4) |
V(1)—O(1V) | 1.600 (3) | O(1B)—C(8B) | 1.338 (5) |
V(1)—O(2V) | 1.775 (2) | O(2V)—C(1P) | 1.420 (6) |
V(1)—N(1A) | 2.207 (3) | ||
O(1A)—V(1)—O(1B) | 153.0 (1) | O(1V)—V(1)—N(1B) | 169.6 (1) |
O(1A)—V(1)—O(1V) | 103.0 (1) | O(2V)—V(1)—N(1A) | 164.8 (1) |
O(1A)—V(1)—O(2V) | 93.7 (1) | O(2V)—V(1)—N(1B) | 86.4 (1) |
O(1A)—V(1)—N(1A) | 76.9 (1) | N(1A)—V(1)—N(1B) | 80.52 (10) |
O(1A)—V(1)—N(1B) | 82.1 (1) | V(1)—O(1A)—C(8A) | 120.8 (2) |
O(1B)—V(1)—O(1V) | 96.2 (1) | V(1)—O(1B)—C(8B) | 123.0 (2) |
O(1B)—V(1)—O(2V) | 100.6 (1) | V(1)—O(2V)—C(1P) | 129.7 (2) |
O(1B)—V(1)—N(1A) | 83.8 (1) | V(1)—N(1A)—C(1A) | 130.5 (3) |
O(1B)—V(1)—N(1B) | 76.2 (1) | V(1)—N(1A)—C(9A) | 111.2 (2) |
O(1V)—V(1)—O(2V) | 102.1 (1) | V(1)—N(1B)—C(1B) | 132.9 (3) |
O(1V)—V(1)—N(1A) | 91.7 (1) | V(1)—N(1B)—C(9B) | 108.5 (2) |
V(1)—O(1A)—C(8A)—C(7A) | 173.7 (3) | O(1V)—V(1)—O(1B)—C(8B) | −174.3 (2) |
V(1)—O(1B)—C(8B)—C(7B) | −178.1 (2) | O(1V)—V(1)—O(2V)—C(1P) | −4.6 (4) |
V(1)—O(2V)—C(1P)—C(2P) | −91.6 (5) | O(2V)—C(1P)—C(2P)—C(3P) | 0 (1) |
O(1A)—V(1)—O(2V)—C(1P) | −108.7 (4) | N(1A)—V(1)—O(1B)—C(8B) | −83.2 (2) |
O(1A)—V(1)—N(1B)—C(1B) | −16.9 (3) | N(1B)—V(1)—O(1A)—C(8A) | −78.1 (2) |
O(1B)—V(1)—O(2V)—C(1P) | 94.2 (4) | N(1B)—V(1)—O(2V)—C(1P) | 169.4 (4) |
O(1V)—V(1)—O(1A)—C(8A) | 92.7 (3) |
8-Hydroxyquinoline (8-quinolinol, oxine) is a well known analytical reagent for forming chelate complexes with metal ions. Its metal complexes with copper(II), zinc(II) or nickel(II) have remarkable antimicrobial or fungicidal activity (Okide et al., 2000; Patel et al., 1999). The bismuth(III) complex also has antitumor activity against leukaemia (Smith et al., 1998). On the other hand, vanadium(IV) and vanadium(V) salts have the insulin-mimetic effects in living animals (Bhattacharyya & Tracey, 2001) or in intact cell systems (Kanamori et al., 2001). Peroxovanadium(V) complexes also show antitumor activity (Djordjevic & Wampler, 1985). These findings need to drive the structural research of various 8-hydroxyquinoline derivatives, as well as vanadium compounds because of their therapeutic value. For these reasons, we aimed to prepare the hybridized compounds of 8-hydroxyquinoline and vanadium, and determine the structure.
Here, we have determined the vanadium(V) complex of 8-hydroxyquinoline, (I). The molecular structure of (I) is shown in Fig. 1. The crystal structures of similar vanadium(V) compounds have been reported, e.g. as the isopropyl ester, oxoisopropoxobis(8-hydroxyquinolinato)vanadium(V) with the VO(OiPr) group (Scheidt, 1973), and as the ethyl ester, oxoetoxobis(5,7-dichloro-8-hydroxquinolinato)vanadium(V) with the VO(OEt) group (González-Baró et al., 1998). These species are considered as inorganic esters (Baran, 2000). Both of the above ester compounds were prepared by the esterification of the oxohydroxobis(8-hydroxyqinolinato)vanadium(V) and oxohydroxobis(5,7-dichloro-8-hydroxyquinolinato)vanadium(V).
While the title compound was obtained directly from the crystallizing mixtures of 8-hydroxyquinoline, VOSO4 and normal propanol. The O atoms of the oxo (V═O) and propoxo (V—OnPr) groups are in the cis configuration with respect to the VO(OnPr) group. Two N atoms of the 8-hydroxyquinoline molecules are located in mutual cis positions, but two O atoms at 8-position are trans. The central VV atom has a distorted octahedral coordination geometry. The overall atomic arrangement of the title compound is the same as that of oxoisopropoxo(8-hydroxyquinolinato)vanadium(V) (Scheidt, 1973), although small differences are present in their geometrical parameters.