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metal-organic compounds
The VV atom of the title complex, [VOL(CH3O)] [L is 3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazonate(2−), C16H14N2O4], has a square pyramidal O4N configuration, with two O atoms and one N atom from the tridentate hydrazone ligand and one O atom from the methoxy group forming the basal plane. The oxo atom is located at the apical position. A layer structure is formed by π–π stacking interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010323/bt6444sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010323/bt6444Isup2.hkl |
CCDC reference: 242036
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.093
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... O4
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.020 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.49 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) V1 - O1 .. 5.44 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.02
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3957 Count of symmetry unique reflns 2314 Completeness (_total/calc) 171.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1643 Fraction of Friedel pairs measured 0.710 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[VO(C16H14N2O4)(CH3O)] | F(000) = 816 |
Mr = 396.27 | Dx = 1.499 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 15303 reflections |
a = 7.531 (3) Å | θ = 3.4–27.5° |
b = 11.787 (4) Å | µ = 0.60 mm−1 |
c = 19.786 (6) Å | T = 296 K |
V = 1756.4 (11) Å3 | Prism, red |
Z = 4 | 0.34 × 0.26 × 0.18 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3957 independent reflections |
Radiation source: fine-focus sealed tube | 3658 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scan | h = −9→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→12 |
Tmin = 0.823, Tmax = 0.899 | l = −25→25 |
15391 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.3631P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3957 reflections | Δρmax = 0.40 e Å−3 |
239 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1643 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.49 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
V1 | 0.17704 (6) | 0.22978 (3) | 0.79629 (2) | 0.0349 (1) | |
N1 | 0.1863 (2) | 0.3437 (1) | 0.71472 (8) | 0.0299 (3) | |
N2 | 0.1285 (3) | 0.3018 (2) | 0.65158 (9) | 0.0347 (4) | |
O1 | −0.0182 (3) | 0.2660 (2) | 0.82253 (9) | 0.0602 (5) | |
O2 | 0.3395 (2) | 0.3283 (1) | 0.83444 (8) | 0.0381 (4) | |
O3 | 0.1369 (2) | 0.1406 (1) | 0.71590 (7) | 0.0345 (3) | |
O4 | 0.2323 (4) | 0.1046 (2) | 0.8386 (1) | 0.0807 (9) | |
O5 | 0.4797 (3) | 0.4284 (1) | 0.94272 (9) | 0.0452 (4) | |
O6 | −0.1355 (2) | −0.0630 (1) | 0.43446 (8) | 0.0404 (4) | |
C1 | 0.3582 (3) | 0.4410 (2) | 0.8326 (1) | 0.0304 (4) | |
C2 | 0.4368 (3) | 0.4969 (2) | 0.8893 (1) | 0.0323 (5) | |
C3 | 0.4614 (3) | 0.6130 (2) | 0.8871 (1) | 0.0393 (5) | |
C4 | 0.4103 (3) | 0.6750 (2) | 0.8296 (1) | 0.0416 (5) | |
C5 | 0.3347 (3) | 0.6230 (2) | 0.7743 (1) | 0.0363 (5) | |
C6 | 0.3065 (3) | 0.5044 (2) | 0.7752 (1) | 0.0301 (4) | |
C7 | 0.2315 (3) | 0.4493 (2) | 0.7161 (1) | 0.0325 (4) | |
C8 | 0.5466 (4) | 0.4816 (2) | 1.0033 (1) | 0.0436 (6) | |
C9 | 0.1042 (3) | 0.1930 (2) | 0.6585 (1) | 0.0290 (4) | |
C10 | 0.0442 (3) | 0.1248 (2) | 0.5997 (1) | 0.0299 (4) | |
C11 | −0.0199 (3) | 0.1757 (2) | 0.5405 (1) | 0.0387 (5) | |
C12 | −0.0784 (3) | 0.1108 (2) | 0.4858 (1) | 0.0388 (5) | |
C13 | −0.0722 (3) | −0.0070 (2) | 0.4902 (1) | 0.0301 (4) | |
C14 | −0.0073 (3) | −0.0590 (2) | 0.5487 (1) | 0.0322 (4) | |
C15 | 0.0499 (3) | 0.0075 (2) | 0.6032 (1) | 0.0326 (5) | |
C16 | −0.1328 (5) | −0.1838 (2) | 0.4363 (1) | 0.0529 (7) | |
C17 | 0.2716 (4) | −0.0079 (2) | 0.8282 (2) | 0.0536 (7) | |
H3 | 0.5121 | 0.6502 | 0.9237 | 0.047* | |
H4 | 0.4278 | 0.7531 | 0.8289 | 0.050* | |
H5 | 0.3025 | 0.6655 | 0.7366 | 0.044* | |
H7 | 0.2152 | 0.4924 | 0.6772 | 0.039* | |
H8A | 0.6550 | 0.5210 | 0.9931 | 0.065* | |
H8B | 0.5690 | 0.4247 | 1.0369 | 0.065* | |
H8C | 0.4604 | 0.5346 | 1.0200 | 0.065* | |
H11 | −0.0234 | 0.2544 | 0.5375 | 0.046* | |
H12 | −0.1211 | 0.1458 | 0.4469 | 0.047* | |
H14 | −0.0021 | −0.1377 | 0.5515 | 0.039* | |
H15 | 0.0922 | −0.0275 | 0.6422 | 0.039* | |
H16A | −0.0126 | −0.2097 | 0.4413 | 0.079* | |
H16B | −0.1816 | −0.2132 | 0.3951 | 0.079* | |
H16C | −0.2023 | −0.2100 | 0.4739 | 0.079* | |
H17A | 0.2785 | −0.0226 | 0.7805 | 0.080* | |
H17B | 0.1802 | −0.0542 | 0.8478 | 0.080* | |
H17C | 0.3834 | −0.0255 | 0.8489 | 0.080* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0577 (2) | 0.0245 (2) | 0.0226 (2) | −0.0102 (2) | 0.0002 (2) | −0.0013 (1) |
N1 | 0.0386 (8) | 0.0255 (7) | 0.0256 (8) | −0.0038 (7) | −0.0018 (8) | −0.0016 (6) |
N2 | 0.049 (1) | 0.0283 (8) | 0.0268 (8) | −0.0060 (7) | −0.0037 (8) | −0.0016 (6) |
O1 | 0.065 (1) | 0.069 (1) | 0.047 (1) | −0.026 (1) | 0.0187 (9) | −0.019 (1) |
O2 | 0.0558 (9) | 0.0249 (7) | 0.0335 (8) | −0.0050 (7) | −0.0137 (8) | 0.0004 (6) |
O3 | 0.0548 (9) | 0.0247 (6) | 0.0239 (7) | −0.0043 (6) | −0.0021 (6) | −0.0016 (5) |
O4 | 0.177 (3) | 0.0268 (8) | 0.0380 (9) | −0.014 (1) | −0.035 (1) | 0.0056 (7) |
O5 | 0.066 (1) | 0.0325 (8) | 0.0373 (9) | 0.0000 (8) | −0.0179 (8) | −0.0025 (7) |
O6 | 0.059 (1) | 0.0321 (8) | 0.0300 (7) | −0.0009 (7) | −0.0098 (7) | −0.0053 (6) |
C1 | 0.034 (1) | 0.0241 (9) | 0.033 (1) | −0.0011 (8) | −0.0017 (8) | −0.0021 (8) |
C2 | 0.035 (1) | 0.030 (1) | 0.032 (1) | 0.0003 (8) | −0.0022 (9) | −0.0024 (9) |
C3 | 0.045 (1) | 0.031 (1) | 0.042 (1) | −0.007 (1) | −0.004 (1) | −0.010 (1) |
C4 | 0.051 (1) | 0.025 (1) | 0.050 (1) | −0.0061 (9) | −0.000 (1) | −0.002 (1) |
C5 | 0.044 (1) | 0.0259 (9) | 0.039 (1) | −0.0018 (9) | 0.001 (1) | 0.0018 (8) |
C6 | 0.035 (1) | 0.0261 (9) | 0.0291 (9) | −0.0028 (8) | 0.0028 (8) | −0.0011 (7) |
C7 | 0.041 (1) | 0.0280 (9) | 0.029 (1) | −0.0014 (8) | −0.0003 (8) | 0.0011 (8) |
C8 | 0.048 (1) | 0.047 (1) | 0.035 (1) | −0.001 (1) | −0.011 (1) | −0.006 (1) |
C9 | 0.034 (1) | 0.029 (1) | 0.0239 (9) | −0.0029 (7) | −0.0002 (8) | −0.0021 (7) |
C10 | 0.036 (1) | 0.0282 (9) | 0.0261 (9) | −0.0037 (8) | 0.0012 (8) | −0.0031 (8) |
C11 | 0.056 (1) | 0.028 (1) | 0.032 (1) | −0.004 (1) | −0.007 (1) | 0.0018 (8) |
C12 | 0.060 (1) | 0.030 (1) | 0.027 (1) | −0.001 (1) | −0.0083 (9) | 0.0014 (9) |
C13 | 0.036 (1) | 0.032 (1) | 0.0231 (9) | −0.0025 (8) | −0.0012 (8) | −0.0032 (8) |
C14 | 0.043 (1) | 0.0233 (9) | 0.030 (1) | 0.0003 (8) | −0.0014 (9) | −0.0014 (7) |
C15 | 0.044 (1) | 0.030 (1) | 0.0237 (9) | 0.0003 (9) | −0.0040 (9) | 0.0021 (8) |
C16 | 0.084 (2) | 0.032 (1) | 0.043 (1) | −0.006 (1) | −0.014 (1) | −0.008 (1) |
C17 | 0.069 (2) | 0.036 (1) | 0.056 (2) | −0.001 (1) | −0.008 (1) | 0.003 (1) |
Geometric parameters (Å, º) top
V1—N1 | 2.100 (2) | C5—H5 | 0.9300 |
V1—O1 | 1.616 (2) | C6—C7 | 1.452 (3) |
V1—O2 | 1.848 (2) | C7—H7 | 0.9300 |
V1—O3 | 1.931 (2) | C8—H8A | 0.9600 |
V1—O4 | 1.747 (2) | C8—H8B | 0.9600 |
N1—C7 | 1.291 (3) | C8—H8C | 0.9600 |
N2—C9 | 1.302 (3) | C9—C10 | 1.484 (3) |
N1—N2 | 1.412 (2) | C10—C11 | 1.403 (3) |
O2—C1 | 1.337 (2) | C10—C15 | 1.384 (3) |
O3—C9 | 1.317 (3) | C11—C12 | 1.397 (3) |
O4—C17 | 1.374 (3) | C11—H11 | 0.9300 |
O5—C2 | 1.369 (3) | C12—C13 | 1.391 (3) |
O5—C8 | 1.444 (3) | C12—H12 | 0.9300 |
O6—C13 | 1.371 (3) | C13—C14 | 1.399 (3) |
O6—C16 | 1.424 (3) | C14—C15 | 1.401 (3) |
C1—C2 | 1.428 (3) | C14—H14 | 0.9300 |
C1—C6 | 1.415 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.382 (3) | C16—H16A | 0.9600 |
C3—C4 | 1.406 (4) | C16—H16B | 0.9600 |
C3—H3 | 0.9300 | C16—H16C | 0.9600 |
C4—C5 | 1.378 (3) | C17—H17A | 0.9600 |
C4—H4 | 0.9300 | C17—H17B | 0.9600 |
C5—C6 | 1.414 (3) | C17—H17C | 0.9600 |
O1—V1—N1 | 96.2 (1) | C4—C5—C6 | 119.4 (2) |
O1—V1—O2 | 107.76 (9) | C4—C5—H5 | 120.3 |
O1—V1—O3 | 105.42 (9) | C5—C4—C3 | 121.6 (2) |
O1—V1—O4 | 106.6 (1) | C5—C4—H4 | 119.2 |
O2—V1—N1 | 83.71 (7) | C5—C6—C7 | 119.3 (2) |
O2—V1—O3 | 141.50 (8) | C6—C1—C2 | 120.1 (2) |
O3—V1—N1 | 73.76 (6) | C6—C5—H5 | 120.3 |
O4—V1—N1 | 154.2 (1) | C6—C7—H7 | 118.3 |
O4—V1—O2 | 100.2 (1) | C7—N1—V1 | 127.5 (1) |
O4—V1—O3 | 88.40 (8) | C7—N1—N2 | 115.9 (2) |
N1—C7—C6 | 123.4 (2) | C9—N2—N1 | 107.2 (2) |
N1—C7—H7 | 118.3 | C9—O3—V1 | 119.0 (1) |
N2—N1—V1 | 116.5 (1) | C10—C11—H11 | 119.3 |
N2—C9—O3 | 121.8 (2) | C10—C15—C14 | 120.7 (2) |
N2—C9—C10 | 119.6 (2) | C10—C15—H15 | 119.6 |
O2—C1—C2 | 118.8 (2) | C11—C10—C9 | 121.8 (2) |
O2—C1—C6 | 121.2 (2) | C11—C12—H12 | 120.4 |
O3—C9—C10 | 118.6 (2) | C12—C11—C10 | 121.4 (2) |
O4—C17—H17A | 109.5 | C12—C11—H11 | 119.3 |
O4—C17—H17B | 109.5 | C12—C13—C14 | 120.1 (2) |
O4—C17—H17C | 109.5 | C13—O6—C16 | 117.1 (2) |
O5—C2—C1 | 115.6 (2) | C13—C12—C11 | 119.2 (2) |
O5—C2—C3 | 125.2 (2) | C13—C12—H12 | 120.4 |
O5—C8—H8A | 109.5 | C13—C14—C15 | 120.0 (2) |
O5—C8—H8B | 109.5 | C13—C14—H14 | 120.0 |
O5—C8—H8C | 109.5 | C14—C15—H15 | 119.6 |
O6—C13—C12 | 114.8 (2) | C15—C10—C9 | 119.5 (2) |
O6—C13—C14 | 125.2 (2) | C15—C10—C11 | 118.7 (2) |
O6—C16—H16A | 109.5 | C15—C14—H14 | 120.0 |
O6—C16—H16B | 109.5 | C17—O4—V1 | 142.6 (2) |
O6—C16—H16C | 109.5 | H8A—C8—H8B | 109.5 |
C1—O2—V1 | 133.1 (1) | H8A—C8—H8C | 109.5 |
C1—C6—C5 | 119.4 (2) | H8B—C8—H8C | 109.5 |
C1—C6—C7 | 121.2 (2) | H16A—C16—H16B | 109.5 |
C2—O5—C8 | 117.8 (2) | H16A—C16—H16C | 109.5 |
C2—C3—C4 | 120.3 (2) | H16B—C16—H16C | 109.5 |
C2—C3—H3 | 119.9 | H17A—C17—H17B | 109.5 |
C3—C2—C1 | 119.2 (2) | H17A—C17—H17C | 109.5 |
C3—C4—H4 | 119.2 | H17B—C17—H17C | 109.5 |
C4—C3—H3 | 119.9 | ||
V1—N1—N2—C9 | −8.4 (2) | O3—C9—C10—C15 | −9.8 (3) |
V1—N1—C7—C6 | 8.1 (3) | O4—V1—N1—N2 | 59.2 (3) |
V1—O2—C1—C2 | 150.3 (2) | O4—V1—N1—C7 | −124.1 (3) |
V1—O2—C1—C6 | −31.6 (3) | O4—V1—O2—C1 | −169.4 (2) |
V1—O3—C9—N2 | 12.2 (3) | O4—V1—O3—C9 | −173.2 (2) |
V1—O3—C9—C10 | −170.0 (2) | O5—C2—C3—C4 | −179.2 (2) |
N1—V1—O2—C1 | 36.4 (2) | O6—C13—C14—C15 | −178.4 (2) |
N1—V1—O3—C9 | −12.1 (2) | C1—C2—C3—C4 | −0.2 (4) |
N1—V1—O4—C17 | −33.3 (6) | C1—C6—C7—N1 | 9.0 (3) |
N1—N2—C9—O3 | −1.7 (3) | C2—C1—C6—C5 | 0.5 (3) |
N1—N2—C9—C10 | −179.4 (2) | C2—C1—C6—C7 | 178.0 (2) |
N2—N1—C7—C6 | −175.2 (2) | C2—C3—C4—C5 | 0.1 (4) |
N2—C9—C10—C15 | 168.0 (2) | C3—C4—C5—C6 | 0.4 (4) |
N2—C9—C10—C11 | −12.5 (3) | C4—C5—C6—C1 | −0.7 (3) |
O1—V1—N1—N2 | −93.1 (2) | C4—C5—C6—C7 | −178.3 (2) |
O1—V1—N1—C7 | 83.6 (2) | C5—C6—C7—N1 | −173.4 (2) |
O1—V1—O2—C1 | −58.2 (2) | C6—C1—C2—O5 | 179.1 (2) |
O1—V1—O3—C9 | 80.0 (2) | C6—C1—C2—C3 | 0.0 (3) |
O1—V1—O4—C17 | 117.9 (4) | C7—N1—N2—C9 | 174.5 (2) |
O2—V1—N1—N2 | 159.7 (2) | C8—O5—C2—C1 | −175.3 (2) |
O2—V1—N1—C7 | −23.6 (2) | C8—O5—C2—C3 | 3.8 (4) |
O2—V1—O3—C9 | −68.7 (2) | C9—C10—C11—C12 | −179.0 (2) |
O2—V1—O4—C17 | −130.0 (4) | C9—C10—C15—C14 | 179.4 (2) |
O2—C1—C2—O5 | −2.8 (3) | C10—C11—C12—C13 | −0.3 (4) |
O2—C1—C2—C3 | 178.1 (2) | C11—C10—C15—C14 | −0.1 (4) |
O2—C1—C6—C5 | −177.6 (2) | C11—C12—C13—O6 | 178.9 (2) |
O2—C1—C6—C7 | −0.1 (3) | C11—C12—C13—C14 | −0.2 (4) |
O3—V1—N1—N2 | 11.2 (1) | C12—C13—C14—C15 | 0.6 (3) |
O3—V1—N1—C7 | −172.1 (2) | C13—C14—C15—C10 | −0.4 (3) |
O3—V1—O2—C1 | 90.2 (2) | C15—C10—C11—C12 | 0.5 (4) |
O3—V1—O4—C17 | 12.2 (4) | C16—O6—C13—C12 | −179.8 (2) |
O3—C9—C10—C11 | 169.7 (2) | C16—O6—C13—C14 | −0.8 (3) |
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