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The vanadium(V) atom in [V(C14H9N3O4)(C13H10NO2)O] is coordinated by an oxo O atom, the N and two O atoms of the tridentate hydrazonate, and the two O atoms of the bidentate hydro­xamate in a distorted octa­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008846/dn6204sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008846/dn6204Isup2.hkl
Contains datablock I

CCDC reference: 270316

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.143
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C12
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.72 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) V1 - N1 .. 5.37 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C22 -C27 1.37 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 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 0 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, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[VO(C14H9N3O4)(C13HNO3)]Z = 2
Mr = 562.40F(000) = 576
Triclinic, P1Dx = 1.465 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.263 (2) ÅCell parameters from 11507 reflections
b = 10.737 (2) Åθ = 3.2–27.5°
c = 12.623 (3) ŵ = 0.44 mm1
α = 86.48 (3)°T = 295 K
β = 86.20 (3)°Prism, red
γ = 66.81 (3)°0.38 × 0.26 × 0.18 mm
V = 1274.8 (5) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5776 independent reflections
Radiation source: fine-focus sealed tube4630 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1312
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1313
Tmin = 0.842, Tmax = 0.923l = 1616
12599 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0859P)2 + 0.1841P]
where P = (Fo2 + 2Fc2)/3
5774 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 0.65 e Å3
45 restraintsΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.87217 (4)0.86418 (4)0.70414 (3)0.05096 (14)
O10.8625 (2)1.02251 (18)0.76143 (12)0.0668 (4)
O20.80913 (16)0.76202 (15)0.61232 (12)0.0576 (4)
O30.5071 (4)0.4483 (3)0.3038 (2)0.1330 (11)
O40.4261 (3)0.6268 (3)0.2035 (2)0.1195 (9)
O50.64929 (15)0.93186 (15)0.75601 (12)0.0570 (4)
O60.87109 (14)0.75369 (16)0.82358 (11)0.0552 (4)
O71.03810 (17)0.79567 (19)0.67808 (13)0.0670 (4)
N10.80580 (18)0.98850 (17)0.56857 (12)0.0488 (4)
N20.7403 (2)0.94427 (17)0.49415 (13)0.0548 (4)
N30.4896 (3)0.5645 (3)0.2796 (2)0.0857 (7)
N40.74313 (17)0.75723 (19)0.86716 (13)0.0522 (4)
C10.8910 (2)1.1274 (2)0.72185 (17)0.0544 (5)
C20.9305 (3)1.2022 (3)0.7897 (2)0.0717 (6)
H20.93951.17700.86160.086*
C30.9562 (3)1.3126 (3)0.7514 (2)0.0788 (7)
H30.98131.36270.79780.095*
C40.9456 (3)1.3510 (3)0.6452 (3)0.0782 (7)
H40.96681.42420.61960.094*
C50.9033 (3)1.2801 (2)0.5772 (2)0.0673 (6)
H50.89341.30760.50580.081*
C60.8749 (2)1.1672 (2)0.61397 (16)0.0520 (4)
C70.8200 (2)1.1011 (2)0.54427 (16)0.0533 (5)
H70.79321.14160.47760.064*
C80.7470 (2)0.8251 (2)0.52563 (16)0.0525 (4)
C90.6811 (2)0.7563 (2)0.46224 (17)0.0563 (5)
C100.6022 (4)0.8211 (3)0.3772 (2)0.0895 (10)
H100.59120.90970.35870.107*
C110.5390 (4)0.7591 (3)0.3184 (2)0.0944 (10)
H110.48420.80550.26170.113*
C120.5574 (3)0.6307 (2)0.3440 (2)0.0676 (6)
C130.6297 (5)0.5638 (3)0.4306 (3)0.1167 (15)
H130.63840.47570.44900.140*
C140.6900 (4)0.6285 (3)0.4908 (3)0.1057 (13)
H140.73720.58460.55130.127*
C150.6286 (2)0.8557 (2)0.82748 (15)0.0477 (4)
C160.4843 (2)0.86970 (19)0.86477 (15)0.0472 (4)
C170.3888 (2)0.8840 (2)0.78782 (18)0.0596 (5)
H170.41800.88040.71630.071*
C180.2506 (3)0.9035 (3)0.8171 (2)0.0788 (7)
H180.18660.91220.76550.095*
C190.2077 (3)0.9100 (3)0.9226 (2)0.0807 (8)
H190.11430.92340.94220.097*
C200.3015 (3)0.8970 (3)0.9995 (2)0.0738 (7)
H200.27090.90331.07070.089*
C210.4409 (3)0.8748 (2)0.97133 (17)0.0588 (5)
H210.50510.86321.02340.071*
C220.7531 (2)0.6502 (2)0.94398 (15)0.0495 (4)
C230.6960 (3)0.5589 (2)0.92532 (18)0.0597 (5)
H230.65080.56520.86260.072*
C240.7059 (3)0.4573 (2)1.0002 (2)0.0705 (6)
H240.66550.39580.98840.085*
C250.7744 (3)0.4457 (3)1.0916 (2)0.0730 (7)
H250.78340.37511.14090.088*
C260.8293 (4)0.5378 (4)1.1098 (3)0.1113 (14)
H260.87380.53151.17290.134*
C270.8201 (4)0.6407 (4)1.0362 (2)0.1050 (13)
H270.85890.70301.04900.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0552 (2)0.0646 (2)0.0437 (2)0.03544 (18)0.01161 (14)0.01212 (15)
O10.0979 (12)0.0824 (10)0.0431 (7)0.0607 (10)0.0041 (7)0.0030 (7)
O20.0678 (9)0.0579 (8)0.0576 (8)0.0351 (7)0.0243 (7)0.0153 (7)
O30.193 (3)0.122 (2)0.136 (2)0.111 (2)0.052 (2)0.0034 (17)
O40.133 (2)0.1107 (17)0.1216 (19)0.0427 (15)0.0677 (17)0.0221 (15)
O50.0554 (8)0.0635 (8)0.0562 (8)0.0295 (7)0.0124 (6)0.0209 (7)
O60.0490 (7)0.0731 (9)0.0519 (7)0.0340 (7)0.0166 (6)0.0211 (7)
O70.0573 (9)0.0940 (12)0.0600 (9)0.0412 (8)0.0113 (7)0.0097 (8)
N10.0568 (9)0.0533 (9)0.0422 (8)0.0280 (7)0.0051 (7)0.0020 (7)
N20.0697 (11)0.0540 (9)0.0455 (8)0.0281 (8)0.0154 (7)0.0036 (7)
N30.0889 (17)0.0856 (16)0.0932 (17)0.0405 (13)0.0147 (13)0.0261 (14)
N40.0502 (9)0.0673 (10)0.0484 (9)0.0339 (8)0.0140 (7)0.0182 (8)
C10.0543 (11)0.0625 (12)0.0538 (11)0.0310 (9)0.0017 (9)0.0019 (9)
C20.0807 (17)0.0836 (16)0.0667 (14)0.0475 (14)0.0162 (12)0.0007 (12)
C30.0869 (18)0.0801 (16)0.0894 (19)0.0511 (15)0.0212 (14)0.0052 (14)
C40.0868 (18)0.0670 (14)0.098 (2)0.0480 (14)0.0121 (15)0.0032 (14)
C50.0799 (16)0.0613 (13)0.0694 (14)0.0381 (12)0.0010 (12)0.0031 (11)
C60.0537 (11)0.0521 (10)0.0539 (11)0.0253 (9)0.0024 (8)0.0031 (9)
C70.0649 (12)0.0545 (11)0.0434 (9)0.0277 (9)0.0002 (8)0.0026 (8)
C80.0562 (11)0.0538 (10)0.0512 (10)0.0247 (9)0.0139 (8)0.0056 (9)
C90.0617 (12)0.0516 (10)0.0586 (12)0.0235 (9)0.0183 (9)0.0017 (9)
C100.136 (3)0.0575 (13)0.0845 (18)0.0415 (15)0.0614 (18)0.0142 (13)
C110.133 (3)0.0691 (15)0.0826 (19)0.0334 (16)0.0591 (19)0.0002 (14)
C120.0664 (14)0.0689 (14)0.0732 (15)0.0292 (11)0.0167 (11)0.0127 (12)
C130.162 (3)0.0799 (19)0.143 (3)0.078 (2)0.084 (3)0.032 (2)
C140.143 (3)0.0804 (18)0.123 (3)0.069 (2)0.086 (2)0.0426 (18)
C150.0533 (10)0.0538 (10)0.0440 (9)0.0293 (9)0.0124 (8)0.0068 (8)
C160.0526 (10)0.0444 (9)0.0498 (10)0.0247 (8)0.0066 (8)0.0026 (8)
C170.0543 (12)0.0693 (13)0.0587 (12)0.0273 (10)0.0116 (9)0.0009 (10)
C180.0534 (13)0.0947 (19)0.0923 (19)0.0324 (13)0.0169 (12)0.0048 (15)
C190.0516 (13)0.0792 (16)0.106 (2)0.0233 (12)0.0089 (14)0.0034 (15)
C200.0810 (17)0.0683 (14)0.0734 (15)0.0339 (13)0.0214 (13)0.0072 (12)
C210.0727 (14)0.0600 (12)0.0527 (11)0.0357 (11)0.0019 (10)0.0020 (9)
C220.0529 (10)0.0582 (11)0.0439 (9)0.0295 (9)0.0134 (8)0.0142 (8)
C230.0777 (14)0.0511 (11)0.0570 (12)0.0304 (10)0.0204 (10)0.0030 (9)
C240.0906 (17)0.0521 (12)0.0806 (16)0.0399 (12)0.0181 (13)0.0073 (11)
C250.0833 (16)0.0737 (15)0.0708 (15)0.0427 (13)0.0168 (12)0.0298 (12)
C260.155 (3)0.147 (3)0.0828 (19)0.113 (3)0.075 (2)0.068 (2)
C270.149 (3)0.138 (3)0.0870 (19)0.118 (3)0.076 (2)0.0645 (19)
Geometric parameters (Å, º) top
V1—O71.5869 (17)C9—C101.368 (3)
V1—O11.8522 (17)C10—C111.371 (3)
V1—O61.8626 (14)C10—H100.9300
V1—O21.9441 (15)C11—C121.337 (3)
V1—N12.0814 (18)C11—H110.9300
V1—O52.1772 (17)C12—C131.361 (4)
O1—C11.333 (3)C13—C141.382 (3)
O2—C81.313 (2)C13—H130.9300
O3—N31.211 (3)C14—H140.9300
O4—N31.206 (3)C15—C161.476 (3)
O5—C151.244 (2)C16—C171.384 (3)
O6—N41.377 (2)C16—C211.386 (3)
N1—C71.290 (3)C17—C181.378 (3)
N1—N21.396 (2)C17—H170.9300
N2—C81.293 (3)C18—C191.371 (4)
N3—C121.479 (3)C18—H180.9300
N4—C151.336 (3)C19—C201.375 (4)
N4—C221.434 (2)C19—H190.9300
C1—C21.389 (3)C20—C211.379 (3)
C1—C61.402 (3)C20—H200.9300
C2—C31.367 (4)C21—H210.9300
C2—H20.9300C22—C231.363 (3)
C3—C41.377 (4)C22—C271.369 (3)
C3—H30.9300C23—C241.376 (3)
C4—C51.376 (4)C23—H230.9300
C4—H40.9300C24—C251.364 (3)
C5—C61.401 (3)C24—H240.9300
C5—H50.9300C25—C261.354 (3)
C6—C71.432 (3)C25—H250.9300
C7—H70.9300C26—C271.376 (3)
C8—C91.476 (3)C26—H260.9300
C9—C141.367 (3)C27—H270.9300
O7—V1—O199.25 (9)C10—C9—C8121.31 (19)
O7—V1—O695.99 (8)C9—C10—C11121.9 (2)
O1—V1—O6103.27 (7)C9—C10—H10119.0
O7—V1—O299.40 (9)C11—C10—H10119.0
O1—V1—O2153.46 (8)C12—C11—C10118.8 (2)
O6—V1—O293.37 (7)C12—C11—H11120.6
O7—V1—N1100.72 (8)C10—C11—H11120.6
O1—V1—N183.29 (7)C11—C12—C13121.5 (2)
O6—V1—N1160.86 (6)C11—C12—N3118.4 (2)
O2—V1—N174.81 (6)C13—C12—N3120.0 (2)
O7—V1—O5171.38 (7)C12—C13—C14119.1 (3)
O1—V1—O584.82 (8)C12—C13—H13120.5
O6—V1—O575.63 (6)C14—C13—H13120.5
O2—V1—O579.40 (7)C9—C14—C13120.6 (2)
N1—V1—O587.25 (7)C9—C14—H14119.7
C1—O1—V1133.27 (14)C13—C14—H14119.7
C8—O2—V1117.10 (13)O5—C15—N4117.10 (18)
C15—O5—V1112.09 (13)O5—C15—C16121.87 (17)
N4—O6—V1119.01 (11)N4—C15—C16120.99 (16)
C7—N1—N2115.93 (16)C17—C16—C21120.0 (2)
C7—N1—V1127.55 (14)C17—C16—C15117.07 (17)
N2—N1—V1116.51 (12)C21—C16—C15122.91 (18)
C8—N2—N1107.89 (16)C18—C17—C16120.0 (2)
O4—N3—O3124.0 (3)C18—C17—H17120.0
O4—N3—C12118.3 (3)C16—C17—H17120.0
O3—N3—C12117.6 (3)C19—C18—C17119.8 (2)
C15—N4—O6115.04 (15)C19—C18—H18120.1
C15—N4—C22129.87 (16)C17—C18—H18120.1
O6—N4—C22114.99 (15)C18—C19—C20120.6 (2)
O1—C1—C2119.3 (2)C18—C19—H19119.7
O1—C1—C6120.92 (19)C20—C19—H19119.7
C2—C1—C6119.7 (2)C19—C20—C21120.2 (2)
C3—C2—C1120.3 (2)C19—C20—H20119.9
C3—C2—H2119.9C21—C20—H20119.9
C1—C2—H2119.9C20—C21—C16119.4 (2)
C2—C3—C4121.0 (2)C20—C21—H21120.3
C2—C3—H3119.5C16—C21—H21120.3
C4—C3—H3119.5C23—C22—C27120.36 (19)
C5—C4—C3119.5 (2)C23—C22—N4120.19 (17)
C5—C4—H4120.2C27—C22—N4119.44 (18)
C3—C4—H4120.2C22—C23—C24119.4 (2)
C4—C5—C6120.9 (2)C22—C23—H23120.3
C4—C5—H5119.5C24—C23—H23120.3
C6—C5—H5119.5C25—C24—C23120.7 (2)
C5—C6—C1118.5 (2)C25—C24—H24119.7
C5—C6—C7120.3 (2)C23—C24—H24119.7
C1—C6—C7121.07 (18)C26—C25—C24119.4 (2)
N1—C7—C6123.81 (18)C26—C25—H25120.3
N1—C7—H7118.1C24—C25—H25120.3
C6—C7—H7118.1C25—C26—C27120.9 (2)
N2—C8—O2122.98 (19)C25—C26—H26119.5
N2—C8—C9118.96 (18)C27—C26—H26119.5
O2—C8—C9118.06 (17)C22—C27—C26119.2 (2)
C14—C9—C10117.8 (2)C22—C27—H27120.4
C14—C9—C8120.8 (2)C26—C27—H27120.4
 

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