Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017692/lh2350sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017692/lh2350Isup2.hkl |
CCDC reference: 647276
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[V(C13H7N3O6)(C2H5O)O(C2H6O)] | F(000) = 1888 |
Mr = 459.28 | Dx = 1.567 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1606 reflections |
a = 21.109 (2) Å | θ = 2.4–24.4° |
b = 8.271 (1) Å | µ = 0.57 mm−1 |
c = 23.249 (3) Å | T = 100 K |
β = 106.38 (1)° | Prism, dark brown |
V = 3894.4 (8) Å3 | 0.44 × 0.20 × 0.04 mm |
Z = 8 |
Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer | 3781 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2446 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.4°, θmin = 4.2° |
Rotation method data acquisition using ω and φ scans | h = −23→25 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −10→9 |
Tmin = 0.789, Tmax = 0.978 | l = −28→29 |
10522 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0783P)2 + 8.9202P] where P = (Fo2 + 2Fc2)/3 |
3781 reflections | (Δ/σ)max < 0.001 |
297 parameters | Δρmax = 1.12 e Å−3 |
1 restraint | Δρmin = −0.56 e Å−3 |
Experimental. 51V NMR (105 MHz, EtOH/CDCl3, p.p.m.): -535; IR (KBr): 962 cm-1 (V═O). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.37285 (19) | 0.4511 (5) | −0.08322 (17) | 0.0178 (9) | |
C2 | 0.3698 (2) | 0.5096 (5) | −0.14007 (18) | 0.0228 (10) | |
H2 | 0.393 (2) | 0.598 (6) | −0.1464 (18) | 0.027* | |
C3 | 0.3305 (2) | 0.4315 (5) | −0.19012 (18) | 0.0230 (10) | |
H3 | 0.329 (2) | 0.472 (5) | −0.2316 (19) | 0.028* | |
C4 | 0.2947 (2) | 0.2937 (5) | −0.18355 (18) | 0.0221 (9) | |
H4 | 0.270 (2) | 0.233 (5) | −0.2200 (18) | 0.027* | |
C5 | 0.2969 (2) | 0.2362 (5) | −0.12764 (18) | 0.0190 (9) | |
H5 | 0.275 (2) | 0.159 (6) | −0.1269 (19) | 0.023* | |
C6 | 0.3365 (2) | 0.3160 (5) | −0.07697 (16) | 0.0156 (8) | |
C7 | 0.3175 (2) | 0.1444 (5) | −0.00180 (17) | 0.0166 (9) | |
H7 | 0.292 (2) | 0.078 (5) | −0.0315 (18) | 0.020* | |
C8 | 0.36449 (19) | 0.1737 (5) | 0.10971 (17) | 0.0164 (9) | |
C9 | 0.3674 (2) | 0.1043 (5) | 0.16606 (17) | 0.0211 (9) | |
C10 | 0.3364 (2) | −0.0376 (5) | 0.17269 (17) | 0.0200 (9) | |
H10 | 0.347 (2) | −0.087 (5) | 0.2193 (18) | 0.024* | |
C11 | 0.2978 (2) | −0.1143 (5) | 0.12121 (17) | 0.0186 (9) | |
C12 | 0.2919 (2) | −0.0521 (5) | 0.06508 (17) | 0.0180 (9) | |
H12 | 0.2645 (19) | −0.110 (5) | 0.0303 (17) | 0.022* | |
C13 | 0.32465 (19) | 0.0889 (5) | 0.05852 (17) | 0.0165 (9) | |
C14 | 0.4726 (2) | 0.7266 (6) | 0.1097 (2) | 0.0321 (11) | |
H14A | 0.4316 | 0.7869 | 0.0905 | 0.039* | |
H14B | 0.5103 | 0.7870 | 0.1028 | 0.039* | |
C15 | 0.4809 (3) | 0.7113 (8) | 0.1751 (2) | 0.0582 (18) | |
H15A | 0.5199 | 0.6451 | 0.1933 | 0.070* | |
H15B | 0.4417 | 0.6598 | 0.1816 | 0.070* | |
H15C | 0.4867 | 0.8189 | 0.1935 | 0.070* | |
C16 | 0.5116 (2) | 0.1545 (5) | 0.0792 (2) | 0.0281 (10) | |
H16A | 0.4776 | 0.0707 | 0.0773 | 0.034* | |
H16B | 0.5230 | 0.2027 | 0.1198 | 0.034* | |
C17 | 0.5718 (2) | 0.0759 (6) | 0.0699 (2) | 0.0397 (13) | |
H17A | 0.6056 | 0.1581 | 0.0714 | 0.048* | |
H17B | 0.5603 | 0.0223 | 0.0308 | 0.048* | |
H17C | 0.5888 | −0.0043 | 0.1016 | 0.048* | |
N1 | 0.34418 (16) | 0.2729 (4) | −0.01624 (13) | 0.0160 (7) | |
N2 | 0.26322 (17) | −0.2627 (4) | 0.12687 (15) | 0.0222 (8) | |
N3 | 0.4043 (2) | 0.1869 (5) | 0.22153 (16) | 0.0304 (9) | |
O1 | 0.34078 (14) | 0.5616 (4) | 0.04592 (12) | 0.0245 (7) | |
O2 | 0.41098 (13) | 0.5200 (3) | −0.03254 (11) | 0.0176 (6) | |
O3 | 0.39724 (14) | 0.3027 (3) | 0.10499 (11) | 0.0208 (6) | |
O4 | 0.46938 (13) | 0.5685 (3) | 0.08408 (11) | 0.0197 (6) | |
O5 | 0.48396 (13) | 0.2797 (3) | 0.03533 (12) | 0.0188 (6) | |
H5A | 0.5138 (15) | 0.333 (5) | 0.0294 (18) | 0.023* | |
O6 | 0.22456 (14) | −0.3178 (3) | 0.08142 (12) | 0.0248 (7) | |
O7 | 0.27483 (18) | −0.3275 (4) | 0.17588 (13) | 0.0414 (9) | |
O8 | 0.4313 (2) | 0.1009 (5) | 0.26400 (15) | 0.0539 (11) | |
O9 | 0.40328 (19) | 0.3340 (4) | 0.22267 (14) | 0.0436 (10) | |
V1 | 0.40196 (3) | 0.45238 (8) | 0.04354 (3) | 0.0173 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.020 (2) | 0.014 (2) | 0.020 (2) | 0.0019 (18) | 0.0046 (16) | −0.0011 (17) |
C2 | 0.024 (2) | 0.019 (2) | 0.025 (2) | −0.0053 (19) | 0.0059 (18) | 0.0027 (18) |
C3 | 0.027 (2) | 0.023 (2) | 0.021 (2) | −0.0005 (19) | 0.0081 (18) | 0.0019 (18) |
C4 | 0.024 (2) | 0.021 (2) | 0.021 (2) | −0.0056 (19) | 0.0064 (18) | −0.0031 (18) |
C5 | 0.020 (2) | 0.010 (2) | 0.028 (2) | −0.0021 (18) | 0.0075 (18) | 0.0010 (17) |
C6 | 0.019 (2) | 0.010 (2) | 0.0187 (19) | −0.0002 (16) | 0.0064 (16) | 0.0013 (15) |
C7 | 0.016 (2) | 0.014 (2) | 0.020 (2) | 0.0015 (17) | 0.0035 (16) | −0.0007 (16) |
C8 | 0.013 (2) | 0.014 (2) | 0.024 (2) | −0.0014 (17) | 0.0071 (16) | −0.0003 (16) |
C9 | 0.023 (2) | 0.019 (2) | 0.020 (2) | −0.0023 (18) | 0.0043 (17) | −0.0047 (17) |
C10 | 0.025 (2) | 0.015 (2) | 0.020 (2) | −0.0003 (18) | 0.0060 (17) | 0.0006 (17) |
C11 | 0.021 (2) | 0.013 (2) | 0.024 (2) | 0.0008 (17) | 0.0094 (17) | 0.0005 (16) |
C12 | 0.017 (2) | 0.015 (2) | 0.021 (2) | 0.0007 (18) | 0.0029 (16) | −0.0046 (17) |
C13 | 0.016 (2) | 0.013 (2) | 0.021 (2) | 0.0010 (16) | 0.0071 (16) | 0.0009 (16) |
C14 | 0.032 (3) | 0.018 (2) | 0.044 (3) | −0.008 (2) | 0.008 (2) | −0.010 (2) |
C15 | 0.065 (4) | 0.057 (4) | 0.043 (3) | 0.017 (3) | −0.001 (3) | −0.028 (3) |
C16 | 0.026 (3) | 0.017 (2) | 0.042 (3) | −0.001 (2) | 0.010 (2) | 0.007 (2) |
C17 | 0.023 (3) | 0.017 (3) | 0.077 (4) | 0.004 (2) | 0.013 (2) | 0.004 (2) |
N1 | 0.0161 (17) | 0.0146 (18) | 0.0176 (16) | −0.0008 (15) | 0.0052 (13) | −0.0018 (14) |
N2 | 0.027 (2) | 0.018 (2) | 0.0232 (19) | −0.0058 (16) | 0.0108 (16) | 0.0017 (15) |
N3 | 0.042 (3) | 0.025 (2) | 0.022 (2) | −0.0090 (19) | 0.0059 (17) | −0.0030 (17) |
O1 | 0.0244 (16) | 0.0209 (17) | 0.0265 (15) | 0.0023 (13) | 0.0042 (12) | −0.0054 (13) |
O2 | 0.0207 (15) | 0.0120 (15) | 0.0175 (13) | −0.0065 (12) | 0.0010 (11) | 0.0009 (11) |
O3 | 0.0234 (16) | 0.0209 (16) | 0.0179 (14) | −0.0061 (13) | 0.0056 (12) | −0.0018 (11) |
O4 | 0.0206 (15) | 0.0144 (15) | 0.0232 (15) | −0.0037 (12) | 0.0045 (12) | −0.0049 (12) |
O5 | 0.0185 (16) | 0.0160 (16) | 0.0211 (14) | −0.0074 (13) | 0.0041 (12) | 0.0022 (12) |
O6 | 0.0266 (17) | 0.0194 (17) | 0.0271 (16) | −0.0055 (13) | 0.0056 (13) | 0.0002 (13) |
O7 | 0.062 (2) | 0.032 (2) | 0.0267 (18) | −0.0168 (18) | 0.0058 (16) | 0.0120 (15) |
O8 | 0.082 (3) | 0.038 (2) | 0.0260 (18) | −0.017 (2) | −0.0096 (18) | 0.0051 (16) |
O9 | 0.073 (3) | 0.026 (2) | 0.0326 (18) | −0.0140 (19) | 0.0165 (18) | −0.0107 (15) |
V1 | 0.0181 (4) | 0.0130 (4) | 0.0205 (4) | −0.0022 (3) | 0.0048 (3) | −0.0021 (3) |
C1—O2 | 1.351 (4) | C14—O4 | 1.431 (5) |
C1—C6 | 1.387 (5) | C14—C15 | 1.486 (7) |
C1—C2 | 1.392 (6) | C14—H14A | 0.9900 |
C2—C3 | 1.384 (6) | C14—H14B | 0.9900 |
C2—H2 | 0.92 (5) | C15—H15A | 0.9800 |
C3—C4 | 1.400 (6) | C15—H15B | 0.9800 |
C3—H3 | 1.01 (4) | C15—H15C | 0.9800 |
C4—C5 | 1.373 (6) | C16—O5 | 1.455 (5) |
C4—H4 | 1.00 (4) | C16—C17 | 1.496 (6) |
C5—C6 | 1.403 (5) | C16—H16A | 0.9900 |
C5—H5 | 0.78 (4) | C16—H16B | 0.9900 |
C6—N1 | 1.420 (5) | C17—H17A | 0.9800 |
C7—N1 | 1.290 (5) | C17—H17B | 0.9800 |
C7—C13 | 1.443 (5) | C17—H17C | 0.9800 |
C7—H7 | 0.93 (4) | N1—V1 | 2.161 (3) |
C8—O3 | 1.293 (5) | N2—O7 | 1.220 (4) |
C8—C9 | 1.416 (5) | N2—O6 | 1.226 (4) |
C8—C13 | 1.432 (5) | N3—O9 | 1.218 (5) |
C9—C10 | 1.374 (6) | N3—O8 | 1.220 (5) |
C9—N3 | 1.473 (5) | O1—V1 | 1.590 (3) |
C10—C11 | 1.396 (6) | O2—V1 | 1.915 (3) |
C10—H10 | 1.12 (4) | O3—V1 | 1.914 (3) |
C11—C12 | 1.375 (5) | O4—V1 | 1.755 (3) |
C11—N2 | 1.453 (5) | O5—V1 | 2.293 (3) |
C12—C13 | 1.386 (6) | O5—H5A | 0.810 (10) |
C12—H12 | 0.98 (4) | ||
O2—C1—C6 | 117.4 (3) | H15A—C15—H15B | 109.5 |
O2—C1—C2 | 122.6 (4) | C14—C15—H15C | 109.5 |
C6—C1—C2 | 120.1 (4) | H15A—C15—H15C | 109.5 |
C3—C2—C1 | 119.5 (4) | H15B—C15—H15C | 109.5 |
C3—C2—H2 | 117 (3) | O5—C16—C17 | 113.4 (4) |
C1—C2—H2 | 123 (3) | O5—C16—H16A | 108.9 |
C2—C3—C4 | 120.1 (4) | C17—C16—H16A | 108.9 |
C2—C3—H3 | 120 (2) | O5—C16—H16B | 108.9 |
C4—C3—H3 | 120 (2) | C17—C16—H16B | 108.9 |
C5—C4—C3 | 120.7 (4) | H16A—C16—H16B | 107.7 |
C5—C4—H4 | 120 (3) | C16—C17—H17A | 109.5 |
C3—C4—H4 | 119 (2) | C16—C17—H17B | 109.5 |
C4—C5—C6 | 119.0 (4) | H17A—C17—H17B | 109.5 |
C4—C5—H5 | 116 (3) | C16—C17—H17C | 109.5 |
C6—C5—H5 | 125 (3) | H17A—C17—H17C | 109.5 |
C1—C6—C5 | 120.5 (4) | H17B—C17—H17C | 109.5 |
C1—C6—N1 | 113.3 (3) | C7—N1—C6 | 122.0 (3) |
C5—C6—N1 | 126.2 (4) | C7—N1—V1 | 127.4 (3) |
N1—C7—C13 | 125.6 (4) | C6—N1—V1 | 110.6 (2) |
N1—C7—H7 | 120 (3) | O7—N2—O6 | 123.5 (4) |
C13—C7—H7 | 114 (3) | O7—N2—C11 | 118.8 (3) |
O3—C8—C9 | 121.9 (3) | O6—N2—C11 | 117.7 (3) |
O3—C8—C13 | 122.4 (3) | O9—N3—O8 | 124.9 (4) |
C9—C8—C13 | 115.6 (4) | O9—N3—C9 | 118.3 (4) |
C10—C9—C8 | 123.5 (4) | O8—N3—C9 | 116.7 (4) |
C10—C9—N3 | 116.7 (4) | C1—O2—V1 | 119.5 (2) |
C8—C9—N3 | 119.8 (4) | C8—O3—V1 | 137.6 (2) |
C9—C10—C11 | 118.3 (4) | C14—O4—V1 | 131.3 (3) |
C9—C10—H10 | 117 (2) | C16—O5—V1 | 123.2 (2) |
C11—C10—H10 | 125 (2) | C16—O5—H5A | 109 (3) |
C12—C11—C10 | 121.2 (4) | V1—O5—H5A | 109 (3) |
C12—C11—N2 | 119.2 (4) | O1—V1—O4 | 102.36 (14) |
C10—C11—N2 | 119.5 (4) | O1—V1—O3 | 97.34 (14) |
C11—C12—C13 | 120.3 (4) | O4—V1—O3 | 99.10 (12) |
C11—C12—H12 | 118 (2) | O1—V1—O2 | 99.18 (13) |
C13—C12—H12 | 121 (2) | O4—V1—O2 | 93.41 (12) |
C12—C13—C8 | 121.0 (4) | O3—V1—O2 | 156.62 (12) |
C12—C13—C7 | 117.1 (4) | O1—V1—N1 | 95.52 (14) |
C8—C13—C7 | 121.9 (4) | O4—V1—N1 | 161.23 (13) |
O4—C14—C15 | 109.0 (4) | O3—V1—N1 | 84.08 (12) |
O4—C14—H14A | 109.9 | O2—V1—N1 | 77.97 (12) |
C15—C14—H14A | 109.9 | O1—V1—O5 | 175.18 (13) |
O4—C14—H14B | 109.9 | O4—V1—O5 | 82.46 (11) |
C15—C14—H14B | 109.9 | O3—V1—O5 | 81.88 (11) |
H14A—C14—H14B | 108.3 | O2—V1—O5 | 80.27 (11) |
C14—C15—H15A | 109.5 | N1—V1—O5 | 79.68 (11) |
C14—C15—H15B | 109.5 | ||
O2—C1—C2—C3 | 178.9 (4) | C8—C9—N3—O9 | 36.2 (6) |
C6—C1—C2—C3 | −0.2 (6) | C10—C9—N3—O8 | 34.0 (6) |
C1—C2—C3—C4 | −0.7 (7) | C8—C9—N3—O8 | −147.1 (4) |
C2—C3—C4—C5 | 1.4 (7) | C6—C1—O2—V1 | −10.2 (5) |
C3—C4—C5—C6 | −1.1 (6) | C2—C1—O2—V1 | 170.5 (3) |
O2—C1—C6—C5 | −178.7 (4) | C9—C8—O3—V1 | −170.8 (3) |
C2—C1—C6—C5 | 0.6 (6) | C13—C8—O3—V1 | 11.2 (6) |
O2—C1—C6—N1 | 1.6 (5) | C15—C14—O4—V1 | 100.7 (4) |
C2—C1—C6—N1 | −179.2 (4) | C17—C16—O5—V1 | −170.3 (3) |
C4—C5—C6—C1 | 0.1 (6) | C14—O4—V1—O1 | −4.6 (4) |
C4—C5—C6—N1 | 179.8 (4) | C14—O4—V1—O3 | −104.3 (3) |
O3—C8—C9—C10 | −176.2 (4) | C14—O4—V1—O2 | 95.6 (3) |
C13—C8—C9—C10 | 2.0 (6) | C14—O4—V1—N1 | 157.3 (4) |
O3—C8—C9—N3 | 5.0 (6) | C14—O4—V1—O5 | 175.3 (3) |
C13—C8—C9—N3 | −176.9 (4) | C8—O3—V1—O1 | 82.5 (4) |
C8—C9—C10—C11 | −2.6 (6) | C8—O3—V1—O4 | −173.7 (4) |
N3—C9—C10—C11 | 176.3 (4) | C8—O3—V1—O2 | −52.2 (5) |
C9—C10—C11—C12 | 1.4 (6) | C8—O3—V1—N1 | −12.3 (4) |
C9—C10—C11—N2 | −178.7 (4) | C8—O3—V1—O5 | −92.7 (4) |
C10—C11—C12—C13 | 0.2 (6) | C1—O2—V1—O1 | −83.4 (3) |
N2—C11—C12—C13 | −179.6 (4) | C1—O2—V1—O4 | 173.5 (3) |
C11—C12—C13—C8 | −0.8 (6) | C1—O2—V1—O3 | 51.0 (4) |
C11—C12—C13—C7 | 178.4 (4) | C1—O2—V1—N1 | 10.3 (3) |
O3—C8—C13—C12 | 177.9 (4) | C1—O2—V1—O5 | 91.7 (3) |
C9—C8—C13—C12 | −0.3 (6) | C7—N1—V1—O1 | −88.7 (3) |
O3—C8—C13—C7 | −1.2 (6) | C6—N1—V1—O1 | 89.5 (3) |
C9—C8—C13—C7 | −179.4 (4) | C7—N1—V1—O4 | 109.0 (5) |
N1—C7—C13—C12 | 179.7 (4) | C6—N1—V1—O4 | −72.8 (5) |
N1—C7—C13—C8 | −1.1 (6) | C7—N1—V1—O3 | 8.1 (3) |
C13—C7—N1—C6 | 177.8 (4) | C6—N1—V1—O3 | −173.7 (3) |
C13—C7—N1—V1 | −4.2 (6) | C7—N1—V1—O2 | 173.0 (4) |
C1—C6—N1—C7 | −175.4 (4) | C6—N1—V1—O2 | −8.7 (2) |
C5—C6—N1—C7 | 4.8 (6) | C7—N1—V1—O5 | 90.9 (3) |
C1—C6—N1—V1 | 6.2 (4) | C6—N1—V1—O5 | −90.9 (2) |
C5—C6—N1—V1 | −173.5 (3) | C16—O5—V1—O1 | −92.7 (16) |
C12—C11—N2—O7 | 171.3 (4) | C16—O5—V1—O4 | 88.7 (3) |
C10—C11—N2—O7 | −8.5 (6) | C16—O5—V1—O3 | −11.7 (3) |
C12—C11—N2—O6 | −7.4 (5) | C16—O5—V1—O2 | −176.5 (3) |
C10—C11—N2—O6 | 172.7 (4) | C16—O5—V1—N1 | −97.1 (3) |
C10—C9—N3—O9 | −142.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.81 (1) | 1.99 (1) | 2.784 (4) | 168 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |