metal-organic compounds
In the title complex, [V(C2O4)O(C12H8N2)(H2O)], a 1,10-phenanthroline molecule and an oxalate dianion chelate to the VIV atom, the distorted octahedral coordination of which is completed by a water molecule and an oxo O atom. The complex molecules are linked across a centre of inversion to form a hydrogen-bonded dimer, and these dimers are linked by another hydrogen bond into a linear chain.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024432/hb6202sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024432/hb6202Isup2.hkl |
CCDC reference: 255408
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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
[V(C2O4)O(C12H8N2)(H2O)] | Z = 2 |
Mr = 353.18 | F(000) = 358 |
Triclinic, P1 | Dx = 1.682 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6328 (7) Å | Cell parameters from 1906 reflections |
b = 9.7800 (9) Å | θ = 2.8–24.3° |
c = 9.8622 (9) Å | µ = 0.75 mm−1 |
α = 89.351 (1)° | T = 295 K |
β = 73.954 (1)° | Prism, green |
γ = 80.565 (1)° | 0.14 × 0.10 × 0.08 mm |
V = 697.5 (1) Å3 |
Data collection top
Bruker APEX CCD area-detector diffractometer | 3105 independent reflections |
Radiation source: fine-focus sealed tube | 2406 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.804, Tmax = 0.943 | k = −12→12 |
7736 measured reflections | l = −12→12 |
Refinement top
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)] = 0.043 | Hydrogen site location: difmap (O-H) and geom (C-H) |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.0065P] where P = (Fo2 + 2Fc2)/3 |
3105 reflections | (Δ/σ)max = 0.001 |
216 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
V1 | 0.51066 (6) | 0.39347 (4) | 0.73480 (5) | 0.0255 (2) | |
O1 | 0.7137 (2) | 0.3988 (2) | 0.5586 (2) | 0.0322 (4) | |
O2 | 1.0198 (3) | 0.3471 (2) | 0.4718 (2) | 0.0477 (6) | |
O3 | 0.7275 (2) | 0.3323 (2) | 0.81050 (19) | 0.0321 (4) | |
O4 | 1.0336 (3) | 0.2842 (2) | 0.7449 (2) | 0.0497 (6) | |
O5 | 0.4474 (3) | 0.5495 (2) | 0.7930 (2) | 0.0491 (6) | |
O1W | 0.3337 (3) | 0.3910 (2) | 0.6140 (2) | 0.0388 (5) | |
N1 | 0.3270 (3) | 0.3145 (2) | 0.9085 (2) | 0.0253 (5) | |
N2 | 0.5494 (3) | 0.1565 (2) | 0.6903 (2) | 0.0288 (5) | |
C1 | 0.3225 (4) | 0.1763 (3) | 0.9120 (3) | 0.0279 (6) | |
C2 | 0.2165 (4) | 0.3934 (3) | 1.0170 (3) | 0.0371 (7) | |
C3 | 0.0970 (4) | 0.3415 (4) | 1.1311 (3) | 0.0477 (8) | |
C4 | 0.0916 (4) | 0.2049 (4) | 1.1346 (3) | 0.0481 (8) | |
C5 | 0.2091 (4) | 0.1149 (3) | 1.0245 (3) | 0.0372 (7) | |
C6 | 0.2178 (5) | −0.0323 (3) | 1.0200 (4) | 0.0481 (8) | |
C7 | 0.3329 (5) | −0.1124 (3) | 0.9121 (4) | 0.0490 (9) | |
C8 | 0.4492 (4) | −0.0541 (3) | 0.7950 (3) | 0.0374 (7) | |
C9 | 0.5747 (5) | −0.1312 (3) | 0.6787 (4) | 0.0493 (9) | |
C10 | 0.6794 (5) | −0.0643 (3) | 0.5729 (4) | 0.0473 (8) | |
C11 | 0.6637 (4) | 0.0778 (3) | 0.5825 (3) | 0.0390 (7) | |
C12 | 0.4450 (4) | 0.0903 (3) | 0.7958 (3) | 0.0282 (6) | |
C13 | 0.8798 (4) | 0.3583 (3) | 0.5677 (3) | 0.0295 (6) | |
C14 | 0.8864 (4) | 0.3203 (3) | 0.7209 (3) | 0.0305 (6) | |
H1W1 | 0.329 (4) | 0.457 (2) | 0.560 (3) | 0.05 (1)* | |
H1W2 | 0.229 (2) | 0.364 (3) | 0.638 (3) | 0.05 (1)* | |
H2 | 0.2192 | 0.4881 | 1.0166 | 0.045* | |
H3 | 0.0212 | 0.4009 | 1.2045 | 0.057* | |
H4 | 0.0102 | 0.1697 | 1.2099 | 0.058* | |
H6 | 0.1416 | −0.0734 | 1.0938 | 0.058* | |
H7 | 0.3371 | −0.2080 | 0.9137 | 0.059* | |
H9 | 0.5860 | −0.2273 | 0.6742 | 0.059* | |
H10 | 0.7612 | −0.1141 | 0.4947 | 0.057* | |
H11 | 0.7373 | 0.1213 | 0.5093 | 0.047* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0250 (3) | 0.0205 (2) | 0.0307 (3) | −0.0059 (2) | −0.0063 (2) | 0.0053 (2) |
O1 | 0.027 (1) | 0.039 (1) | 0.032 (1) | −0.006 (1) | −0.010 (1) | 0.015 (1) |
O2 | 0.032 (1) | 0.064 (2) | 0.039 (1) | −0.001 (1) | 0.001 (1) | 0.005 (1) |
O3 | 0.030 (1) | 0.041 (1) | 0.028 (1) | −0.014 (1) | −0.008 (1) | 0.008 (1) |
O4 | 0.032 (1) | 0.074 (2) | 0.052 (1) | −0.017 (1) | −0.022 (1) | 0.029 (1) |
O5 | 0.053 (1) | 0.024 (1) | 0.062 (2) | −0.010 (1) | −0.001 (1) | 0.001 (1) |
O1W | 0.029 (1) | 0.044 (1) | 0.049 (1) | −0.013 (1) | −0.018 (1) | 0.022 (1) |
N1 | 0.027 (1) | 0.021 (1) | 0.029 (1) | −0.005 (1) | −0.009 (1) | 0.003 (1) |
N2 | 0.028 (1) | 0.025 (1) | 0.034 (1) | −0.003 (1) | −0.011 (1) | −0.001 (1) |
C1 | 0.031 (1) | 0.028 (1) | 0.032 (1) | −0.011 (1) | −0.016 (1) | 0.008 (1) |
C2 | 0.042 (2) | 0.034 (2) | 0.034 (2) | −0.010 (1) | −0.007 (1) | −0.003 (1) |
C3 | 0.049 (2) | 0.055 (2) | 0.032 (2) | −0.010 (2) | 0.002 (1) | −0.003 (1) |
C4 | 0.050 (2) | 0.064 (2) | 0.033 (2) | −0.024 (2) | −0.008 (2) | 0.017 (2) |
C5 | 0.039 (2) | 0.042 (2) | 0.040 (2) | −0.019 (1) | −0.018 (1) | 0.016 (1) |
C6 | 0.054 (2) | 0.042 (2) | 0.060 (2) | −0.024 (2) | −0.027 (2) | 0.030 (2) |
C7 | 0.060 (2) | 0.030 (2) | 0.071 (2) | −0.023 (2) | −0.033 (2) | 0.019 (2) |
C8 | 0.042 (2) | 0.024 (1) | 0.0563 (19) | −0.006 (1) | −0.030 (2) | 0.005 (1) |
C9 | 0.061 (2) | 0.025 (2) | 0.070 (2) | −0.004 (2) | −0.033 (2) | −0.007 (2) |
C10 | 0.049 (2) | 0.033 (2) | 0.057 (2) | 0.008 (1) | −0.018 (2) | −0.016 (2) |
C11 | 0.036 (2) | 0.038 (2) | 0.041 (2) | −0.004 (1) | −0.009 (1) | −0.005 (1) |
C12 | 0.031 (1) | 0.023 (1) | 0.037 (2) | −0.009 (1) | −0.018 (1) | 0.006 (1) |
C13 | 0.032 (1) | 0.025 (1) | 0.033 (2) | −0.006 (1) | −0.010 (1) | 0.005 (1) |
C14 | 0.032 (2) | 0.026 (1) | 0.039 (2) | −0.011 (1) | −0.015 (1) | 0.009 (1) |
Geometric parameters (Å, º) top
V1—O1 | 1.990 (2) | C5—C6 | 1.431 (4) |
V1—O3 | 2.001 (2) | C6—C7 | 1.340 (5) |
V1—O5 | 1.586 (2) | C7—C8 | 1.426 (5) |
V1—O1W | 2.036 (2) | C8—C9 | 1.406 (5) |
V1—N1 | 2.120 (2) | C8—C12 | 1.407 (4) |
V1—N2 | 2.319 (2) | C9—C10 | 1.361 (5) |
O1—C13 | 1.292 (3) | C10—C11 | 1.377 (4) |
O2—C13 | 1.206 (3) | C13—C14 | 1.564 (4) |
O3—C14 | 1.277 (3) | O1W—H1W1 | 0.84 (1) |
O4—C14 | 1.207 (3) | O1W—H1W2 | 0.86 (1) |
N1—C2 | 1.326 (3) | C2—H2 | 0.93 |
N1—C1 | 1.357 (3) | C3—H3 | 0.93 |
N2—C11 | 1.330 (3) | C4—H4 | 0.93 |
N2—C12 | 1.354 (3) | C6—H6 | 0.93 |
C1—C5 | 1.402 (4) | C7—H7 | 0.93 |
C1—C12 | 1.437 (4) | C9—H9 | 0.93 |
C2—C3 | 1.388 (4) | C10—H10 | 0.93 |
C3—C4 | 1.343 (4) | C11—H11 | 0.93 |
C4—C5 | 1.409 (4) | ||
O1—V1—O3 | 80.8 (1) | C9—C8—C12 | 116.6 (3) |
O1—V1—O5 | 105.3 (1) | C9—C8—C7 | 124.6 (3) |
O1—V1—O1W | 88.7 (1) | C12—C8—C7 | 118.7 (3) |
O1—V1—N1 | 160.4 (1) | C10—C9—C8 | 119.5 (3) |
O1—V1—N2 | 87.2 (1) | C9—C10—C11 | 119.6 (3) |
O3—V1—O5 | 101.8 (1) | N2—C11—C10 | 123.8 (3) |
O3—V1—O1W | 158.9 (1) | N2—C12—C8 | 123.6 (3) |
O3—V1—N1 | 92.4 (1) | N2—C12—C1 | 116.3 (2) |
O3—V1—N2 | 80.9 (1) | C8—C12—C1 | 120.1 (3) |
O5—V1—O1W | 98.5 (1) | O2—C13—O1 | 126.2 (3) |
O5—V1—N1 | 94.0 (1) | O2—C13—C14 | 120.8 (2) |
O5—V1—N2 | 167.5 (1) | O1—C13—C14 | 113.0 (2) |
O1W—V1—N1 | 91.6 (1) | O4—C14—O3 | 126.2 (3) |
O1W—V1—N2 | 80.4 (1) | O4—C14—C13 | 119.8 (2) |
N1—V1—N2 | 73.6 (1) | O3—C14—C13 | 113.9 (2) |
C13—O1—V1 | 116.2 (2) | V1—O1W—H1W1 | 115 (2) |
C14—O3—V1 | 116.0 (2) | V1—O1W—H1W2 | 127 (2) |
C2—N1—C1 | 117.5 (2) | H1W1—O1W—H1W2 | 109 (2) |
C2—N1—V1 | 123.2 (2) | N1—C2—H2 | 118.4 |
C1—N1—V1 | 119.3 (2) | C3—C2—H2 | 118.4 |
C11—N2—C12 | 116.8 (2) | C4—C3—H3 | 120.2 |
C11—N2—V1 | 129.9 (2) | C2—C3—H3 | 120.2 |
C12—N2—V1 | 113.2 (2) | C3—C4—H4 | 120.0 |
N1—C1—C5 | 123.1 (3) | C5—C4—H4 | 120.0 |
N1—C1—C12 | 117.5 (2) | C7—C6—H6 | 119.2 |
C5—C1—C12 | 119.4 (2) | C5—C6—H6 | 119.2 |
N1—C2—C3 | 123.2 (3) | C6—C7—H7 | 119.4 |
C4—C3—C2 | 119.6 (3) | C8—C7—H7 | 119.4 |
C3—C4—C5 | 120.0 (3) | C10—C9—H9 | 120.2 |
C1—C5—C4 | 116.6 (3) | C8—C9—H9 | 120.2 |
C1—C5—C6 | 118.9 (3) | C9—C10—H10 | 120.2 |
C4—C5—C6 | 124.5 (3) | C11—C10—H10 | 120.2 |
C7—C6—C5 | 121.6 (3) | N2—C11—H11 | 118.1 |
C6—C7—C8 | 121.3 (3) | C10—C11—H11 | 118.1 |
O5—V1—O1—C13 | 102.7 (2) | N1—C1—C5—C4 | 2.3 (4) |
O3—V1—O1—C13 | 2.85 (18) | C12—C1—C5—C4 | −179.7 (2) |
O1W—V1—O1—C13 | −158.81 (19) | N1—C1—C5—C6 | −178.4 (2) |
N1—V1—O1—C13 | −67.8 (3) | C12—C1—C5—C6 | −0.4 (4) |
N2—V1—O1—C13 | −78.38 (19) | C3—C4—C5—C1 | −2.5 (4) |
O5—V1—O3—C14 | −105.7 (2) | C3—C4—C5—C6 | 178.2 (3) |
O1—V1—O3—C14 | −1.88 (18) | C1—C5—C6—C7 | 0.8 (4) |
O1W—V1—O3—C14 | 59.1 (3) | C4—C5—C6—C7 | −179.9 (3) |
N1—V1—O3—C14 | 159.68 (19) | C5—C6—C7—C8 | −1.5 (5) |
N2—V1—O3—C14 | 86.70 (19) | C6—C7—C8—C9 | 179.3 (3) |
O5—V1—N1—C2 | −1.8 (2) | C6—C7—C8—C12 | 1.7 (4) |
O1—V1—N1—C2 | 169.0 (2) | C12—C8—C9—C10 | −2.0 (4) |
O3—V1—N1—C2 | 100.2 (2) | C7—C8—C9—C10 | −179.7 (3) |
O1W—V1—N1—C2 | −100.5 (2) | C8—C9—C10—C11 | 1.2 (5) |
N2—V1—N1—C2 | −180.0 (2) | C12—N2—C11—C10 | 0.5 (4) |
O5—V1—N1—C1 | 179.30 (19) | V1—N2—C11—C10 | 176.3 (2) |
O1—V1—N1—C1 | −9.9 (3) | C9—C10—C11—N2 | −0.5 (5) |
O3—V1—N1—C1 | −78.65 (18) | C11—N2—C12—C8 | −1.4 (4) |
O1W—V1—N1—C1 | 80.63 (19) | V1—N2—C12—C8 | −177.9 (2) |
N2—V1—N1—C1 | 1.15 (17) | C11—N2—C12—C1 | 179.8 (2) |
O5—V1—N2—C11 | 173.2 (5) | V1—N2—C12—C1 | 3.2 (3) |
O1—V1—N2—C11 | −2.0 (2) | C9—C8—C12—N2 | 2.2 (4) |
O3—V1—N2—C11 | −83.1 (2) | C7—C8—C12—N2 | −180.0 (3) |
O1W—V1—N2—C11 | 87.1 (2) | C9—C8—C12—C1 | −179.0 (3) |
N1—V1—N2—C11 | −178.3 (2) | C7—C8—C12—C1 | −1.2 (4) |
O5—V1—N2—C12 | −10.9 (6) | N1—C1—C12—N2 | −2.4 (3) |
O1—V1—N2—C12 | 173.96 (18) | C5—C1—C12—N2 | 179.5 (2) |
O3—V1—N2—C12 | 92.82 (18) | N1—C1—C12—C8 | 178.7 (2) |
O1W—V1—N2—C12 | −96.93 (18) | C5—C1—C12—C8 | 0.6 (4) |
N1—V1—N2—C12 | −2.36 (17) | V1—O1—C13—O2 | 175.9 (2) |
C2—N1—C1—C5 | −0.7 (4) | V1—O1—C13—C14 | −3.1 (3) |
V1—N1—C1—C5 | 178.22 (19) | V1—O3—C14—O4 | −179.6 (2) |
C2—N1—C1—C12 | −178.8 (2) | V1—O3—C14—C13 | 0.8 (3) |
V1—N1—C1—C12 | 0.2 (3) | O2—C13—C14—O4 | 2.9 (4) |
C1—N1—C2—C3 | −0.8 (4) | O1—C13—C14—O4 | −178.1 (3) |
V1—N1—C2—C3 | −179.7 (2) | O2—C13—C14—O3 | −177.5 (3) |
N1—C2—C3—C4 | 0.5 (5) | O1—C13—C14—O3 | 1.6 (3) |
C2—C3—C4—C5 | 1.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O1i | 0.84 (1) | 1.86 (1) | 2.697 (3) | 173 (3) |
O1W—H1W2···O4ii | 0.86 (1) | 1.85 (1) | 2.671 (3) | 160 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z. |