Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035295/zl2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035295/zl2048Isup2.hkl |
CCDC reference: 657628
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.109
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.01 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1 (2) 2.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Okabe, Wada et al. (2002); Okabe, Muranishi et al. (2002).
The title complex was prepared by the addition of a stoichiometric amount of cobalt chloride (20 mmol) to a hot aqueous solution (25 ml) of 5-butyl-pyridyl-2-carboxylic acid (fusaric acid, 30 mmol). The pH was then adjusted to 7.0–8.0 with NaOH (30 mmol). The resulting solution was filtered, and red crystals were obtained at room temperature on slow evaporation of the solvent over several days.
Carbon-bound H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 or 1.5 Ueq(C). Water H atoms were tentatively located in difference Fourier maps and were refined with distance restraints of O–H = 0.82 Å and H···H = 1.29 Å, each within a standard deviation of 0.01 Å; other H-atoms with Uiso(H) = 1.2 Ueq(O).
Some structures of transition metal complexes containing the 5-butyl-pyridyl-2-carboxylic acid (fusaric acid) ligand have been reported. In the structural investigation of these complexes, it has been found that the fusaric acid functions as a multidentate ligand (Okabe, Wada et al., 2002; Okabe, Muranishi et al., 2002), with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, (I), a new Co complex obtained by the reaction of fusaric acid with cobalt chloride in aqueous solution.
As illustrated in Fig. 1, the CoII atom, which is a neutral mononuclear molecule, lies on a centre of symmetry and has a distorted octahedral geometry with six coordinating atoms being two carboxyl O and two N atoms from two different fusaric acid ligands and two water molecules (Table 1). The coordinating O and N atoms and CoII atom are coplanar. The structural components are connected through O—H···O hydrogen bonding involving the coordinating water molecules as donors and the carboxyl O atoms as acceptors, forming neutral layers perpendicular to b axis (Fig. 2; Table 2).
For related literature, see: Okabe, Wada et al. (2002); Okabe, Muranishi et al. (2002).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
[Co(C10H12NO2)2(H2O)2] | F(000) = 474 |
Mr = 451.37 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2500 reflections |
a = 5.1378 (1) Å | θ = 1.4–28.0° |
b = 34.0034 (9) Å | µ = 0.82 mm−1 |
c = 7.5922 (2) Å | T = 223 K |
β = 124.181 (2)° | Lamellar, red |
V = 1097.27 (5) Å3 | 0.25 × 0.12 × 0.10 mm |
Z = 2 |
Bruker APEXII area-detector diffractometer | 2511 independent reflections |
Radiation source: fine-focus sealed tube | 1528 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.822, Tmax = 0.923 | k = −43→32 |
9237 measured reflections | l = −9→9 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3 |
2511 reflections | (Δ/σ)max < 0.001 |
140 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
[Co(C10H12NO2)2(H2O)2] | V = 1097.27 (5) Å3 |
Mr = 451.37 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.1378 (1) Å | µ = 0.82 mm−1 |
b = 34.0034 (9) Å | T = 223 K |
c = 7.5922 (2) Å | 0.25 × 0.12 × 0.10 mm |
β = 124.181 (2)° |
Bruker APEXII area-detector diffractometer | 2511 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1528 reflections with I > 2σ(I) |
Tmin = 0.822, Tmax = 0.923 | Rint = 0.056 |
9237 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.31 e Å−3 |
2511 reflections | Δρmin = −0.70 e Å−3 |
140 parameters |
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 | ||
Co1 | 0.5000 | 1.0000 | 1.0000 | 0.03057 (19) | |
O1 | 0.9434 (4) | 0.98064 (6) | 1.2377 (3) | 0.0348 (5) | |
O1W | 0.5780 (5) | 0.98681 (7) | 0.7663 (4) | 0.0454 (6) | |
H1W | 0.698 (8) | 0.9997 (9) | 0.764 (6) | 0.068* | |
H2W | 0.480 (8) | 0.9701 (10) | 0.680 (5) | 0.068* | |
O2 | 1.1879 (4) | 0.93289 (6) | 1.4790 (3) | 0.0448 (6) | |
N1 | 0.4053 (5) | 0.94044 (6) | 1.0289 (4) | 0.0321 (6) | |
C1 | 0.9548 (6) | 0.94757 (9) | 1.3189 (5) | 0.0336 (7) | |
C2 | 0.6498 (6) | 0.92409 (8) | 1.2061 (4) | 0.0316 (7) | |
C3 | 0.6270 (6) | 0.88849 (8) | 1.2802 (5) | 0.0427 (8) | |
H3 | 0.8022 | 0.8776 | 1.4047 | 0.051* | |
C4 | 0.3432 (7) | 0.86867 (8) | 1.1698 (5) | 0.0458 (8) | |
H4 | 0.3234 | 0.8445 | 1.2209 | 0.055* | |
C5 | 0.0877 (6) | 0.88440 (8) | 0.9838 (5) | 0.0370 (7) | |
C6 | 0.1329 (6) | 0.92054 (8) | 0.9207 (5) | 0.0354 (7) | |
H6 | −0.0371 | 0.9318 | 0.7949 | 0.043* | |
C7 | −0.2300 (7) | 0.86463 (8) | 0.8580 (5) | 0.0457 (8) | |
H7A | −0.3810 | 0.8825 | 0.7444 | 0.055* | |
H7B | −0.3010 | 0.8601 | 0.9521 | 0.055* | |
C8 | −0.2326 (6) | 0.82584 (8) | 0.7594 (5) | 0.0446 (8) | |
H8A | −0.1665 | 0.8303 | 0.6624 | 0.054* | |
H8B | −0.0795 | 0.8081 | 0.8722 | 0.054* | |
C9 | −0.5523 (7) | 0.80628 (10) | 0.6378 (5) | 0.0581 (10) | |
H9A | −0.7079 | 0.8248 | 0.5314 | 0.070* | |
H9B | −0.6120 | 0.8003 | 0.7368 | 0.070* | |
C10 | −0.5619 (10) | 0.76872 (12) | 0.5266 (7) | 0.0948 (14) | |
H10A | −0.5030 | 0.7744 | 0.4282 | 0.142* | |
H10B | −0.7731 | 0.7579 | 0.4488 | 0.142* | |
H10C | −0.4158 | 0.7498 | 0.6316 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0264 (3) | 0.0264 (3) | 0.0351 (3) | −0.0030 (2) | 0.0149 (2) | −0.0004 (3) |
O1 | 0.0269 (10) | 0.0321 (12) | 0.0398 (12) | −0.0050 (9) | 0.0153 (9) | 0.0012 (10) |
O1W | 0.0395 (13) | 0.0501 (16) | 0.0516 (16) | −0.0185 (10) | 0.0287 (12) | −0.0153 (11) |
O2 | 0.0362 (11) | 0.0369 (13) | 0.0387 (13) | 0.0003 (9) | 0.0073 (10) | 0.0002 (10) |
N1 | 0.0286 (12) | 0.0266 (14) | 0.0389 (14) | −0.0026 (10) | 0.0176 (12) | −0.0008 (11) |
C1 | 0.0320 (15) | 0.0300 (17) | 0.0370 (18) | −0.0024 (13) | 0.0183 (15) | −0.0058 (14) |
C2 | 0.0320 (15) | 0.0258 (16) | 0.0330 (17) | −0.0007 (12) | 0.0160 (14) | −0.0014 (13) |
C3 | 0.0431 (18) | 0.0366 (19) | 0.0394 (19) | −0.0018 (15) | 0.0178 (16) | 0.0057 (15) |
C4 | 0.053 (2) | 0.0317 (18) | 0.053 (2) | −0.0074 (16) | 0.0297 (18) | 0.0084 (16) |
C5 | 0.0409 (17) | 0.0249 (17) | 0.050 (2) | −0.0058 (13) | 0.0286 (16) | −0.0048 (14) |
C6 | 0.0320 (15) | 0.0266 (17) | 0.0444 (19) | −0.0028 (13) | 0.0194 (14) | −0.0041 (14) |
C7 | 0.0408 (17) | 0.0341 (18) | 0.064 (2) | −0.0085 (14) | 0.0308 (18) | −0.0058 (16) |
C8 | 0.0434 (17) | 0.0375 (19) | 0.052 (2) | −0.0067 (15) | 0.0261 (16) | −0.0041 (16) |
C9 | 0.055 (2) | 0.046 (2) | 0.070 (3) | −0.0183 (17) | 0.033 (2) | −0.0118 (19) |
C10 | 0.106 (3) | 0.057 (3) | 0.099 (4) | −0.027 (2) | 0.044 (3) | −0.032 (2) |
Co1—O1i | 2.0641 (18) | C4—H4 | 0.9400 |
Co1—O1 | 2.0641 (18) | C5—C6 | 1.385 (4) |
Co1—O1Wi | 2.076 (2) | C5—C7 | 1.509 (4) |
Co1—O1W | 2.076 (2) | C6—H6 | 0.9400 |
Co1—N1i | 2.123 (2) | C7—C8 | 1.513 (4) |
Co1—N1 | 2.123 (2) | C7—H7A | 0.9800 |
O1—C1 | 1.268 (3) | C7—H7B | 0.9800 |
O1W—H1W | 0.76 (3) | C8—C9 | 1.513 (4) |
O1W—H2W | 0.80 (3) | C8—H8A | 0.9800 |
O2—C1 | 1.235 (3) | C8—H8B | 0.9800 |
N1—C2 | 1.341 (3) | C9—C10 | 1.517 (5) |
N1—C6 | 1.342 (3) | C9—H9A | 0.9800 |
C1—C2 | 1.523 (4) | C9—H9B | 0.9800 |
C2—C3 | 1.367 (4) | C10—H10A | 0.9700 |
C3—C4 | 1.382 (4) | C10—H10B | 0.9700 |
C3—H3 | 0.9400 | C10—H10C | 0.9700 |
C4—C5 | 1.386 (4) | ||
O1i—Co1—O1 | 180.000 (1) | C3—C4—H4 | 119.9 |
O1i—Co1—O1Wi | 91.72 (9) | C5—C4—H4 | 119.9 |
O1—Co1—O1Wi | 88.28 (8) | C6—C5—C4 | 116.6 (3) |
O1i—Co1—O1W | 88.28 (8) | C6—C5—C7 | 120.5 (3) |
O1—Co1—O1W | 91.72 (9) | C4—C5—C7 | 122.8 (3) |
O1Wi—Co1—O1W | 180.000 (2) | N1—C6—C5 | 123.8 (3) |
O1i—Co1—N1i | 79.04 (8) | N1—C6—H6 | 118.1 |
O1—Co1—N1i | 100.96 (8) | C5—C6—H6 | 118.1 |
O1Wi—Co1—N1i | 92.73 (9) | C5—C7—C8 | 114.0 (2) |
O1W—Co1—N1i | 87.27 (9) | C5—C7—H7A | 108.7 |
O1i—Co1—N1 | 100.96 (8) | C8—C7—H7A | 108.7 |
O1—Co1—N1 | 79.04 (8) | C5—C7—H7B | 108.7 |
O1Wi—Co1—N1 | 87.27 (9) | C8—C7—H7B | 108.7 |
O1W—Co1—N1 | 92.73 (9) | H7A—C7—H7B | 107.6 |
N1i—Co1—N1 | 180.000 (1) | C9—C8—C7 | 112.9 (2) |
C1—O1—Co1 | 115.76 (16) | C9—C8—H8A | 109.0 |
Co1—O1W—H1W | 116 (3) | C7—C8—H8A | 109.0 |
Co1—O1W—H2W | 121 (3) | C9—C8—H8B | 109.0 |
H1W—O1W—H2W | 122 (4) | C7—C8—H8B | 109.0 |
C2—N1—C6 | 118.2 (2) | H8A—C8—H8B | 107.8 |
C2—N1—Co1 | 111.06 (17) | C8—C9—C10 | 113.2 (3) |
C6—N1—Co1 | 129.70 (18) | C8—C9—H9A | 108.9 |
O2—C1—O1 | 126.2 (3) | C10—C9—H9A | 108.9 |
O2—C1—C2 | 117.7 (3) | C8—C9—H9B | 108.9 |
O1—C1—C2 | 116.1 (2) | C10—C9—H9B | 108.9 |
N1—C2—C3 | 122.1 (2) | H9A—C9—H9B | 107.7 |
N1—C2—C1 | 115.8 (2) | C9—C10—H10A | 109.5 |
C3—C2—C1 | 122.1 (3) | C9—C10—H10B | 109.5 |
C2—C3—C4 | 119.2 (3) | H10A—C10—H10B | 109.5 |
C2—C3—H3 | 120.4 | C9—C10—H10C | 109.5 |
C4—C3—H3 | 120.4 | H10A—C10—H10C | 109.5 |
C3—C4—C5 | 120.2 (3) | H10B—C10—H10C | 109.5 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O2ii | 0.80 (3) | 1.90 (3) | 2.688 (3) | 170 (3) |
O1W—H1W···O1iii | 0.76 (3) | 1.97 (3) | 2.712 (3) | 165 (3) |
Symmetry codes: (ii) x−1, y, z−1; (iii) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C10H12NO2)2(H2O)2] |
Mr | 451.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 223 |
a, b, c (Å) | 5.1378 (1), 34.0034 (9), 7.5922 (2) |
β (°) | 124.181 (2) |
V (Å3) | 1097.27 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.82 |
Crystal size (mm) | 0.25 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.822, 0.923 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9237, 2511, 1528 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.109, 1.02 |
No. of reflections | 2511 |
No. of parameters | 140 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.70 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
Co1—O1 | 2.0641 (18) | Co1—N1 | 2.123 (2) |
Co1—O1W | 2.076 (2) | ||
O1i—Co1—O1Wi | 91.72 (9) | O1i—Co1—N1 | 100.96 (8) |
O1—Co1—O1Wi | 88.28 (8) | O1—Co1—N1 | 79.04 (8) |
O1i—Co1—O1W | 88.28 (8) | O1Wi—Co1—N1 | 87.27 (9) |
O1—Co1—O1W | 91.72 (9) | O1W—Co1—N1 | 92.73 (9) |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O2ii | 0.80 (3) | 1.90 (3) | 2.688 (3) | 170 (3) |
O1W—H1W···O1iii | 0.76 (3) | 1.97 (3) | 2.712 (3) | 165 (3) |
Symmetry codes: (ii) x−1, y, z−1; (iii) −x+2, −y+2, −z+2. |
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Some structures of transition metal complexes containing the 5-butyl-pyridyl-2-carboxylic acid (fusaric acid) ligand have been reported. In the structural investigation of these complexes, it has been found that the fusaric acid functions as a multidentate ligand (Okabe, Wada et al., 2002; Okabe, Muranishi et al., 2002), with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, (I), a new Co complex obtained by the reaction of fusaric acid with cobalt chloride in aqueous solution.
As illustrated in Fig. 1, the CoII atom, which is a neutral mononuclear molecule, lies on a centre of symmetry and has a distorted octahedral geometry with six coordinating atoms being two carboxyl O and two N atoms from two different fusaric acid ligands and two water molecules (Table 1). The coordinating O and N atoms and CoII atom are coplanar. The structural components are connected through O—H···O hydrogen bonding involving the coordinating water molecules as donors and the carboxyl O atoms as acceptors, forming neutral layers perpendicular to b axis (Fig. 2; Table 2).