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Acta Cryst. (2007). E63, m1753
https://doi.org/10.1107/S1600536807023987
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2,9-Dimethyl-1,10-phenanthrolinium dioxido(pyridine-2,6-dicarboxylato)­vanadate(V) mono­hydrate

H. Aghabozorg and E. Sadr-khanlou
In the title compound, (C14H13N2)[V(C7H3NO4)O2]·H2O, the VV atom has a distorted trigonal–bipyramidal coordination environment formed by one pyridyl N atom and two O atoms of the [VO2]+ group occupying the equatorial plane, and two carboxyl­ate O atoms occupying the axial positions. O—H...O, N—H...O, O—H...N and C—H...O hydrogen bonds, together with π–π stacking inter­actions [average centroid-to-centroid distance 3.644 (12) Å], seem to be effective in the stabilization of the crystal structure, resulting in the formation of a three-dimensional supra­molecular structure.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023987/hk2236sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023987/hk2236Isup2.hkl
Contains datablock I

CCDC reference: 601618

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.102
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........         H5
                    C5     H5
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         H5
                    H5     O4
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........         H5
                    C5     H5     O4
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          7


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for V1          (4)       4.77


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

In recent years, the fundamental coordination chemistry and characterization of vanadium compounds have attracted considerable attention, due to their actions in biological systems. A five coordinated vanadium(V) complex with the same ligand was previously reported (Ranjbar, 2004) in which one (C7H3NO4) anion was attached to a metal center. We herein report the crystal structure of the title compound, (I).

The molecule of (I) contains one (C14H13N2)+ cation, one water molecule and one [V(C7H3NO4)(O2)]- anion, where the vanadium(V) atom has a distorted trigonal bipyramidal coordination environment (Fig. 1, Table 1). The coordinated pyridyl nitrogen atom (N1) and two oxygen atoms (O1V, O2V) of the VO2+ group occupy the distorted equatorial plane, while the two carboxylate oxygen atoms (O1 and O3) occupy the axial positions around the central atom.

The V1—O1V [1.6228 (14) Å] and V1—O2V [1.6158 (14) Å] bonds are shorter than V1—O1 [2.0132 (13) Å] and V1—O3 [1.9842 (13) Å] bonds, due to the formation of double bonds. The water molecule resides between two ionic units making a bridge-like hydrogen bond. Beside the classic hydrogen bonds, there are also C—H···O type hydrogen bonds (Table 2), which are responsible for stabilization of the crystal network. Each vanadium(V) complex is attached to the neighboring complex and four (C14H13N2)+ units via C—H···O interactions. These interactions, coming inconcert, make an infinite layers which could be described by R22 (10), C22 (15) and R33(13) graph set descriptors (Fig. 2). Furthermore, considering the average values for intercentroid [3.644 (12) Å] and interplanar [3.297 (16) Å] distances for (C14H13N2)+ ions [symmetry codes: x, y, z; x - 1, y, z; -x, -y, -z + 2; -x - 1, -y, -z + 2], the π-π stacking interaction between cations can be established. Thus, the three-dimensional supramolecular structure for (I) is confirmed.

Related literature top

For related literature, see: Ranjbar (2004).

Experimental top

A pale yellow colored vanadium(V) complex of cation and anion as a proton transfer agent, the title compound, (I), was isolated at pH = 3.0 by stirring an aqueous mixture of the ligand [2,9-dimethyl-1,10-phenathroline (21.2 mg) and pyridine-2,6-dicarboxylic acid (13.9 mg) in water (10 ml)] with 0.5 molar equivalent of vanadium(III) chloride (8.1 mg) at room temperature (yield; 1.79 mg, 73%, m.p. 450 K). Slow evaporation of the solvent during two weeks resulted in X-ray quality crystals. Elemental analysis revealed that one molecule of water is associated as solvate.

Refinement top

H atoms were positioned geometrically, with N—H = 0.88 Å (for NH), O—H = 0.85 Å (for OH2) and C—H = 0.95 and 0.98 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N,O), where x = 1.5 for water and methyl H, and x = 1.2 for all other H atoms.

Structure description top

In recent years, the fundamental coordination chemistry and characterization of vanadium compounds have attracted considerable attention, due to their actions in biological systems. A five coordinated vanadium(V) complex with the same ligand was previously reported (Ranjbar, 2004) in which one (C7H3NO4) anion was attached to a metal center. We herein report the crystal structure of the title compound, (I).

The molecule of (I) contains one (C14H13N2)+ cation, one water molecule and one [V(C7H3NO4)(O2)]- anion, where the vanadium(V) atom has a distorted trigonal bipyramidal coordination environment (Fig. 1, Table 1). The coordinated pyridyl nitrogen atom (N1) and two oxygen atoms (O1V, O2V) of the VO2+ group occupy the distorted equatorial plane, while the two carboxylate oxygen atoms (O1 and O3) occupy the axial positions around the central atom.

The V1—O1V [1.6228 (14) Å] and V1—O2V [1.6158 (14) Å] bonds are shorter than V1—O1 [2.0132 (13) Å] and V1—O3 [1.9842 (13) Å] bonds, due to the formation of double bonds. The water molecule resides between two ionic units making a bridge-like hydrogen bond. Beside the classic hydrogen bonds, there are also C—H···O type hydrogen bonds (Table 2), which are responsible for stabilization of the crystal network. Each vanadium(V) complex is attached to the neighboring complex and four (C14H13N2)+ units via C—H···O interactions. These interactions, coming inconcert, make an infinite layers which could be described by R22 (10), C22 (15) and R33(13) graph set descriptors (Fig. 2). Furthermore, considering the average values for intercentroid [3.644 (12) Å] and interplanar [3.297 (16) Å] distances for (C14H13N2)+ ions [symmetry codes: x, y, z; x - 1, y, z; -x, -y, -z + 2; -x - 1, -y, -z + 2], the π-π stacking interaction between cations can be established. Thus, the three-dimensional supramolecular structure for (I) is confirmed.

For related literature, see: Ranjbar (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Graph set descriptors made by different X—H···O interactions.
2,9-Dimethyl-1,10-phenanthrolinium dioxo(pyridine-2,6-dicarboxylato)vanadate(V) monohydrate top
Crystal data top
(C14H13N2)[V(C7H3NO4)O2]·H2OZ = 2
Mr = 475.32F(000) = 488
Triclinic, P1Dx = 1.584 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1194 (12) ÅCell parameters from 921 reflections
b = 10.6843 (19) Åθ = 2.3–27.8°
c = 13.480 (2) ŵ = 0.55 mm−1
α = 81.166 (3)°T = 120 K
β = 82.397 (3)°Prism, yellow
γ = 81.959 (4)°0.05 × 0.05 × 0.02 mm
V = 996.8 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4398 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 27.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −9→8
Tmin = 0.973, Tmax = 0.989k = −13→13
7763 measured reflectionsl = −17→17
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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.102H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.5169P]
where P = (Fo2 + 2Fc2)/3
4398 reflections(Δ/σ)max = 0.001
291 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
(C14H13N2)[V(C7H3NO4)O2]·H2Oγ = 81.959 (4)°
Mr = 475.32V = 996.8 (3) Å3
Triclinic, P1Z = 2
a = 7.1194 (12) ÅMo Kα radiation
b = 10.6843 (19) ŵ = 0.55 mm−1
c = 13.480 (2) ÅT = 120 K
α = 81.166 (3)°0.05 × 0.05 × 0.02 mm
β = 82.397 (3)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4398 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		3677 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.989Rint = 0.019
7763 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.96Δρmax = 0.40 e Å−3
4398 reflectionsΔρmin = −0.34 e Å−3
291 parameters
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
V10.23632 (4)0.53331 (3)0.71259 (2)0.02141 (11)
O1V0.4234 (2)0.50716 (13)0.77320 (10)0.0315 (3)
O2V0.0597 (2)0.47362 (12)0.78294 (10)0.0287 (3)
O10.3179 (2)0.39575 (12)0.62365 (10)0.0271 (3)
O20.3574 (2)0.33281 (14)0.47038 (11)0.0366 (3)
O30.1639 (2)0.71802 (12)0.72049 (9)0.0275 (3)
O40.0581 (2)0.91366 (12)0.64817 (11)0.0314 (3)
N10.1910 (2)0.61833 (13)0.56431 (11)0.0198 (3)
C10.3060 (3)0.41282 (17)0.52667 (14)0.0253 (4)
C20.2222 (2)0.54682 (17)0.48962 (13)0.0226 (4)
C30.1809 (3)0.59740 (19)0.39317 (14)0.0281 (4)
H3A0.20570.54700.33960.034*
C40.1022 (3)0.7240 (2)0.37720 (14)0.0317 (4)
H4A0.06840.76030.31220.038*
C50.0721 (3)0.79869 (18)0.45546 (14)0.0275 (4)
H5A0.01990.88590.44480.033*
C60.1212 (2)0.74101 (17)0.54953 (13)0.0224 (4)
C70.1099 (3)0.80042 (17)0.64506 (14)0.0234 (4)
N1A0.3456 (2)0.04478 (13)1.20580 (11)0.0196 (3)
H1AA0.3654−0.03871.22120.024*
N2A0.2998 (2)−0.11965 (13)1.07341 (11)0.0200 (3)
C1A0.3719 (3)0.11637 (17)1.27465 (13)0.0228 (4)
C2A0.3398 (3)0.24933 (18)1.25092 (14)0.0264 (4)
H2AA0.35760.30231.29860.032*
C3A0.2831 (3)0.30303 (17)1.15923 (14)0.0253 (4)
H3AA0.26140.39331.14380.030*
C4A0.2563 (2)0.22627 (16)1.08750 (13)0.0212 (3)
C5A0.2000 (3)0.27714 (17)0.98954 (14)0.0240 (4)
H5AA0.17630.36690.97140.029*
C6A0.1804 (3)0.19858 (17)0.92258 (13)0.0239 (4)
H6AA0.14360.23420.85800.029*
C7A0.2141 (2)0.06288 (17)0.94763 (13)0.0206 (3)
C8A0.1947 (2)−0.02266 (18)0.88038 (13)0.0242 (4)
H8AA0.15900.00900.81490.029*
C9A0.2276 (3)−0.15098 (18)0.91015 (14)0.0249 (4)
H9AA0.2154−0.20900.86530.030*
C10A0.2799 (2)−0.19738 (17)1.00801 (14)0.0224 (4)
C11A0.2681 (2)0.00837 (16)1.04333 (12)0.0185 (3)
C12A0.2899 (2)0.09300 (16)1.11330 (13)0.0193 (3)
C13A0.4363 (3)0.05058 (19)1.37274 (14)0.0307 (4)
H13A0.3685−0.02421.39600.046*
H13B0.40860.10951.42330.046*
H13C0.57400.02341.36330.046*
C14A0.3109 (3)−0.33859 (17)1.04256 (15)0.0279 (4)
H14A0.4198−0.35821.08220.042*
H14B0.3369−0.38430.98360.042*
H14C0.1962−0.36531.08440.042*
O1S0.5167 (2)0.20247 (13)0.73847 (10)0.0354 (4)
H1S0.45100.25440.69820.053*
H2S0.51600.24020.78970.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.02635 (19)0.01819 (16)0.02035 (16)0.00025 (12)−0.00783 (12)−0.00297 (11)
O1V0.0338 (8)0.0301 (7)0.0333 (7)−0.0017 (6)−0.0154 (6)−0.0052 (6)
O2V0.0318 (8)0.0257 (7)0.0278 (7)−0.0021 (6)−0.0038 (6)−0.0020 (5)
O10.0326 (7)0.0213 (6)0.0281 (7)0.0028 (5)−0.0091 (6)−0.0064 (5)
O20.0482 (9)0.0301 (7)0.0334 (7)−0.0019 (7)−0.0013 (7)−0.0154 (6)
O30.0386 (8)0.0202 (6)0.0246 (6)0.0012 (5)−0.0092 (6)−0.0054 (5)
O40.0360 (8)0.0195 (6)0.0380 (7)0.0012 (6)−0.0054 (6)−0.0046 (5)
N10.0191 (7)0.0201 (7)0.0214 (7)−0.0036 (6)−0.0049 (6)−0.0032 (5)
C10.0242 (9)0.0250 (9)0.0283 (9)−0.0043 (7)−0.0031 (7)−0.0075 (7)
C20.0199 (9)0.0254 (9)0.0244 (8)−0.0067 (7)−0.0018 (7)−0.0062 (7)
C30.0279 (10)0.0358 (10)0.0227 (9)−0.0096 (8)−0.0033 (7)−0.0051 (7)
C40.0318 (11)0.0405 (11)0.0233 (9)−0.0092 (9)−0.0099 (8)0.0042 (8)
C50.0260 (10)0.0262 (9)0.0294 (9)−0.0035 (7)−0.0071 (8)0.0023 (7)
C60.0178 (9)0.0213 (8)0.0281 (9)−0.0040 (7)−0.0033 (7)−0.0015 (7)
C70.0210 (9)0.0217 (8)0.0279 (9)−0.0024 (7)−0.0036 (7)−0.0037 (7)
N1A0.0195 (7)0.0168 (7)0.0226 (7)−0.0020 (5)−0.0025 (6)−0.0031 (5)
N2A0.0169 (7)0.0185 (7)0.0245 (7)−0.0010 (5)−0.0023 (6)−0.0036 (5)
C1A0.0190 (9)0.0273 (9)0.0232 (8)−0.0037 (7)−0.0009 (7)−0.0073 (7)
C2A0.0261 (10)0.0247 (9)0.0307 (9)−0.0048 (7)−0.0007 (7)−0.0116 (7)
C3A0.0226 (9)0.0187 (8)0.0343 (10)−0.0018 (7)0.0008 (7)−0.0067 (7)
C4A0.0169 (8)0.0188 (8)0.0270 (9)−0.0009 (6)−0.0002 (7)−0.0034 (7)
C5A0.0196 (9)0.0187 (8)0.0312 (9)−0.0005 (7)−0.0022 (7)0.0018 (7)
C6A0.0192 (9)0.0266 (9)0.0229 (8)0.0000 (7)−0.0028 (7)0.0034 (7)
C7A0.0143 (8)0.0248 (9)0.0215 (8)−0.0009 (7)−0.0008 (6)−0.0020 (7)
C8A0.0182 (9)0.0340 (10)0.0203 (8)−0.0026 (7)−0.0014 (7)−0.0048 (7)
C9A0.0183 (9)0.0308 (9)0.0273 (9)−0.0030 (7)0.0003 (7)−0.0117 (7)
C10A0.0156 (8)0.0233 (9)0.0290 (9)−0.0023 (7)−0.0001 (7)−0.0084 (7)
C11A0.0135 (8)0.0202 (8)0.0211 (8)−0.0008 (6)−0.0006 (6)−0.0032 (6)
C12A0.0148 (8)0.0204 (8)0.0221 (8)−0.0019 (6)−0.0014 (6)−0.0024 (6)
C13A0.0365 (11)0.0322 (10)0.0254 (9)−0.0052 (8)−0.0079 (8)−0.0059 (8)
C14A0.0260 (10)0.0214 (9)0.0376 (10)−0.0017 (7)−0.0045 (8)−0.0086 (7)
O1S0.0530 (10)0.0245 (7)0.0245 (7)0.0098 (6)−0.0066 (6)−0.0009 (5)
Geometric parameters (Å, º) top
V1—O2V1.6158 (14)C2A—C3A1.367 (3)
V1—O1V1.6228 (14)C2A—H2AA0.9500
V1—O31.9842 (13)C3A—C4A1.407 (2)
V1—O12.0132 (13)C3A—H3AA0.9500
V1—N12.1107 (15)C4A—C12A1.407 (2)
O1—C11.304 (2)C4A—C5A1.435 (2)
O2—C11.216 (2)C5A—C6A1.356 (3)
O3—C71.300 (2)C5A—H5AA0.9500
O4—C71.220 (2)C6A—C7A1.431 (2)
N1—C61.330 (2)C6A—H6AA0.9500
N1—C21.333 (2)C7A—C11A1.410 (2)
C1—C21.508 (3)C7A—C8A1.414 (2)
C2—C31.382 (3)C8A—C9A1.364 (3)
C3—C41.385 (3)C8A—H8AA0.9500
C3—H3A0.9500C9A—C10A1.415 (3)
C4—C51.396 (3)C9A—H9AA0.9500
C4—H4A0.9500C10A—C14A1.503 (2)
C5—C61.388 (3)C11A—C12A1.439 (2)
C5—H5A0.9500C13A—H13A0.9800
C6—C71.509 (2)C13A—H13B0.9800
N1A—C1A1.336 (2)C13A—H13C0.9800
N1A—C12A1.361 (2)C14A—H14A0.9800
N1A—H1AA0.8800C14A—H14B0.9800
N2A—C10A1.333 (2)C14A—H14C0.9800
N2A—C11A1.362 (2)O1S—H1S0.8500
C1A—C2A1.401 (3)O1S—H2S0.8500
C1A—C13A1.496 (3)
O2V—V1—O1V109.64 (7)C1A—C2A—H2AA119.9
O2V—V1—O3101.07 (6)C2A—C3A—C4A120.83 (16)
O1V—V1—O399.96 (6)C2A—C3A—H3AA119.6
O2V—V1—O199.69 (6)C4A—C3A—H3AA119.6
O1V—V1—O196.56 (6)C3A—C4A—C12A117.84 (16)
O3—V1—O1147.22 (6)C3A—C4A—C5A123.32 (16)
O2V—V1—N1117.60 (6)C12A—C4A—C5A118.82 (16)
O1V—V1—N1132.68 (7)C6A—C5A—C4A120.78 (16)
O3—V1—N174.31 (5)C6A—C5A—H5AA119.6
O1—V1—N173.66 (5)C4A—C5A—H5AA119.6
C1—O1—V1123.69 (12)C5A—C6A—C7A121.08 (16)
C7—O3—V1123.61 (11)C5A—C6A—H6AA119.5
C6—N1—C2121.89 (15)C7A—C6A—H6AA119.5
C6—N1—V1118.44 (11)C11A—C7A—C8A116.76 (16)
C2—N1—V1119.56 (12)C11A—C7A—C6A120.21 (16)
O2—C1—O1125.46 (18)C8A—C7A—C6A123.02 (16)
O2—C1—C2122.44 (17)C9A—C8A—C7A119.59 (16)
O1—C1—C2112.09 (15)C9A—C8A—H8AA120.2
N1—C2—C3121.01 (17)C7A—C8A—H8AA120.2
N1—C2—C1110.77 (15)C8A—C9A—C10A119.85 (16)
C3—C2—C1128.21 (16)C8A—C9A—H9AA120.1
C2—C3—C4117.85 (17)C10A—C9A—H9AA120.1
C2—C3—H3A121.1N2A—C10A—C9A122.26 (16)
C4—C3—H3A121.1N2A—C10A—C14A117.51 (16)
C3—C4—C5120.81 (17)C9A—C10A—C14A120.22 (16)
C3—C4—H4A119.6N2A—C11A—C7A123.74 (15)
C5—C4—H4A119.6N2A—C11A—C12A118.19 (15)
C6—C5—C4117.57 (17)C7A—C11A—C12A118.07 (15)
C6—C5—H5A121.2N1A—C12A—C4A118.81 (15)
C4—C5—H5A121.2N1A—C12A—C11A120.16 (15)
N1—C6—C5120.82 (16)C4A—C12A—C11A121.03 (15)
N1—C6—C7110.84 (15)C1A—C13A—H13A109.5
C5—C6—C7128.34 (16)C1A—C13A—H13B109.5
O4—C7—O3125.37 (17)H13A—C13A—H13B109.5
O4—C7—C6122.36 (17)C1A—C13A—H13C109.5
O3—C7—C6112.26 (15)H13A—C13A—H13C109.5
C1A—N1A—C12A124.06 (15)H13B—C13A—H13C109.5
C1A—N1A—H1AA118.0C10A—C14A—H14A109.5
C12A—N1A—H1AA118.0C10A—C14A—H14B109.5
C10A—N2A—C11A117.80 (15)H14A—C14A—H14B109.5
N1A—C1A—C2A118.35 (16)C10A—C14A—H14C109.5
N1A—C1A—C13A118.39 (16)H14A—C14A—H14C109.5
C2A—C1A—C13A123.25 (16)H14B—C14A—H14C109.5
C3A—C2A—C1A120.10 (16)H1S—O1S—H2S105.4
C3A—C2A—H2AA119.9
O2V—V1—O1—C1114.46 (15)C5—C6—C7—O4−2.4 (3)
O1V—V1—O1—C1−134.26 (15)N1—C6—C7—O3−2.3 (2)
O3—V1—O1—C1−14.2 (2)C5—C6—C7—O3178.65 (18)
N1—V1—O1—C1−1.63 (14)C12A—N1A—C1A—C2A0.2 (3)
O2V—V1—O3—C7−110.14 (15)C12A—N1A—C1A—C13A−179.04 (16)
O1V—V1—O3—C7137.39 (15)N1A—C1A—C2A—C3A0.0 (3)
O1—V1—O3—C718.2 (2)C13A—C1A—C2A—C3A179.25 (17)
N1—V1—O3—C75.67 (14)C1A—C2A—C3A—C4A−0.1 (3)
O2V—V1—N1—C687.64 (14)C2A—C3A—C4A—C12A0.0 (3)
O1V—V1—N1—C6−96.02 (14)C2A—C3A—C4A—C5A−178.93 (17)
O3—V1—N1—C6−6.85 (12)C3A—C4A—C5A—C6A178.56 (17)
O1—V1—N1—C6−179.80 (14)C12A—C4A—C5A—C6A−0.4 (3)
O2V—V1—N1—C2−88.52 (14)C4A—C5A—C6A—C7A0.3 (3)
O1V—V1—N1—C287.82 (15)C5A—C6A—C7A—C11A0.2 (3)
O3—V1—N1—C2176.99 (14)C5A—C6A—C7A—C8A179.76 (17)
O1—V1—N1—C24.04 (13)C11A—C7A—C8A—C9A0.2 (2)
V1—O1—C1—O2178.41 (15)C6A—C7A—C8A—C9A−179.36 (16)
V1—O1—C1—C2−0.6 (2)C7A—C8A—C9A—C10A0.3 (3)
C6—N1—C2—C3−0.7 (3)C11A—N2A—C10A—C9A0.0 (2)
V1—N1—C2—C3175.31 (13)C11A—N2A—C10A—C14A−178.67 (15)
C6—N1—C2—C1178.57 (15)C8A—C9A—C10A—N2A−0.4 (3)
V1—N1—C2—C1−5.41 (19)C8A—C9A—C10A—C14A178.24 (16)
O2—C1—C2—N1−175.26 (18)C10A—N2A—C11A—C7A0.5 (2)
O1—C1—C2—N13.8 (2)C10A—N2A—C11A—C12A−179.80 (15)
O2—C1—C2—C34.0 (3)C8A—C7A—C11A—N2A−0.6 (2)
O1—C1—C2—C3−176.96 (18)C6A—C7A—C11A—N2A178.95 (15)
N1—C2—C3—C4−1.4 (3)C8A—C7A—C11A—C12A179.72 (15)
C1—C2—C3—C4179.45 (17)C6A—C7A—C11A—C12A−0.7 (2)
C2—C3—C4—C52.2 (3)C1A—N1A—C12A—C4A−0.4 (3)
C3—C4—C5—C6−0.9 (3)C1A—N1A—C12A—C11A179.01 (16)
C2—N1—C6—C52.1 (3)C3A—C4A—C12A—N1A0.2 (2)
V1—N1—C6—C5−173.99 (13)C5A—C4A—C12A—N1A179.21 (15)
C2—N1—C6—C7−177.03 (15)C3A—C4A—C12A—C11A−179.14 (15)
V1—N1—C6—C76.90 (18)C5A—C4A—C12A—C11A−0.2 (2)
C4—C5—C6—N1−1.2 (3)N2A—C11A—C12A—N1A1.6 (2)
C4—C5—C6—C7177.70 (17)C7A—C11A—C12A—N1A−178.66 (15)
V1—O3—C7—O4177.30 (14)N2A—C11A—C12A—C4A−179.01 (15)
V1—O3—C7—C6−3.7 (2)C7A—C11A—C12A—C4A0.7 (2)
N1—C6—C7—O4176.67 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1Si0.881.872.714 (2)162
O1S—H1S···O10.851.892.728 (2)168
O1S—H2S···N2Ai0.852.492.964 (2)116
C2A—H2AA···O2ii0.952.393.241 (2)149
C5—H5···O4iii0.952.343.238 (2)157
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y, z+1; (iii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula(C14H13N2)[V(C7H3NO4)O2]·H2O
Mr475.32
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)7.1194 (12), 10.6843 (19), 13.480 (2)
α, β, γ (°)81.166 (3), 82.397 (3), 81.959 (4)
V (Å3)996.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.55
Crystal size (mm)0.05 × 0.05 × 0.02
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.973, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		7763, 4398, 3677
Rint0.019
(sin θ/λ)max (Å−1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 0.96
No. of reflections4398
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.40, −0.34

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SAINT-Plus, SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
V1—O2V1.6158 (14)V1—O12.0132 (13)
V1—O1V1.6228 (14)V1—N12.1107 (15)
V1—O31.9842 (13)
O2V—V1—O1V109.64 (7)O3—V1—O1147.22 (6)
O2V—V1—O3101.07 (6)O2V—V1—N1117.60 (6)
O1V—V1—O399.96 (6)O1V—V1—N1132.68 (7)
O2V—V1—O199.69 (6)O3—V1—N174.31 (5)
O1V—V1—O196.56 (6)O1—V1—N173.66 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1Si0.8801.8652.714 (2)161.45
O1S—H1S···O10.8501.8912.728 (2)168.08
O1S—H2S···N2Ai0.8502.4942.964 (2)115.71
C2A—H2AA···O2ii0.9502.393.241 (2)149
C5—H5···O4iii0.9502.343.238 (2)157
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y, z+1; (iii) −x, −y+2, −z+1.
 

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