Acta Cryst. (2008). E64, m78 [ doi:10.1107/S1600536807062186 ]
In the title compound, [Co(NCS)2(C11H13NO2)2], a mononuclear Schiff base cobalt(II) complex, the Co atom is six-coordinated by four O atoms from two Schiff base ligands, and by two N atoms from two thiocyanate ligands, forming a distorted octahedral geometry. The central Co atom lies on a twofold rotation axis. An intramolecular N-H
O hydrogen bond is present.
The title compound was obtained by stirring of 3-methoxysalicylaldehyde (0.2 mmol, 30.5 mg), cyclopropylamine (0.2 mmol, 11.5 mg), ammonium thiocyanate (0.2 mmol, 15.2 mg), and cobalt(II) acetate (0.1 mmol, 25.0 mg) in methanol (20 ml) for 30 min. The reaction mixture was then filtered. Brown block-shaped single crystals suitable for X-ray diffraction were formed from the filtrate after nine days.
H1 was located from a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2 or 1.5Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
![[Figure 1]](./gd2028fig1thm.gif)
| Fig. 1. The molecular structure of title compound, showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level |
| [Co(NCS)2(C11H13NO2)2] | F000 = 1156 |
| Mr = 557.54 | Dx = 1.417 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 1290 reflections |
| a = 21.851 (3) Å | θ = 2.5–24.3º |
| b = 7.6424 (11) Å | µ = 0.85 mm−1 |
| c = 16.073 (2) Å | T = 298 (2) K |
| β = 103.196 (3)º | Block, brown |
| V = 2613.2 (6) Å3 | 0.23 × 0.20 × 0.17 mm |
| Z = 4 |
| Bruker SMART APEX area-detector diffractometer | 2962 independent reflections |
| Radiation source: fine-focus sealed tube | 1960 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.055 |
| T = 298(2) K | θmax = 27.5º |
| ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→28 |
| Tmin = 0.828, Tmax = 0.869 | k = −9→9 |
| 10900 measured reflections | l = −20→20 |
| 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)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.3065P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2962 reflections | Δρmax = 0.39 e Å−3 |
| 163 parameters | Δρmin = −0.24 e Å−3 |
| 1 restraint | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Co(NCS)2(C11H13NO2)2] | V = 2613.2 (6) Å3 |
| Mr = 557.54 | Z = 4 |
| Monoclinic, C2/c | Mo Kα |
| a = 21.851 (3) Å | µ = 0.85 mm−1 |
| b = 7.6424 (11) Å | T = 298 (2) K |
| c = 16.073 (2) Å | 0.23 × 0.20 × 0.17 mm |
| β = 103.196 (3)º |
| Bruker SMART APEX area-detector diffractometer | 2962 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1960 reflections with I > 2σ(I) |
| Tmin = 0.828, Tmax = 0.869 | Rint = 0.055 |
| 10900 measured reflections |
| R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
| wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Δρmax = 0.39 e Å−3 |
| 2962 reflections | Δρmin = −0.24 e Å−3 |
| 163 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 | 0.87110 (8) | 0.2500 | 0.0439 (2) | |
| N1 | 0.41206 (13) | 0.8517 (4) | −0.02768 (16) | 0.0525 (7) | |
| N2 | 0.42546 (13) | 1.0362 (4) | 0.23494 (17) | 0.0583 (7) | |
| O1 | 0.47825 (9) | 0.7998 (3) | 0.12725 (12) | 0.0507 (5) | |
| O2 | 0.57533 (10) | 0.6595 (3) | 0.22880 (14) | 0.0590 (6) | |
| S1 | 0.30172 (5) | 1.14011 (15) | 0.17478 (7) | 0.0854 (4) | |
| C1 | 0.51623 (15) | 0.7354 (4) | 0.00295 (19) | 0.0491 (8) | |
| C2 | 0.52171 (13) | 0.7346 (4) | 0.09220 (18) | 0.0437 (7) | |
| C3 | 0.57669 (14) | 0.6617 (4) | 0.1437 (2) | 0.0485 (8) | |
| C4 | 0.62403 (15) | 0.6003 (4) | 0.1085 (2) | 0.0621 (9) | |
| H4 | 0.6601 | 0.5533 | 0.1435 | 0.075* | |
| C5 | 0.61837 (18) | 0.6079 (5) | 0.0207 (3) | 0.0704 (11) | |
| H5 | 0.6511 | 0.5680 | −0.0025 | 0.085* | |
| C6 | 0.56587 (17) | 0.6727 (4) | −0.0313 (2) | 0.0626 (9) | |
| H6 | 0.5625 | 0.6760 | −0.0900 | 0.075* | |
| C7 | 0.46021 (15) | 0.7952 (4) | −0.0526 (2) | 0.0529 (8) | |
| H7 | 0.4582 | 0.7934 | −0.1110 | 0.063* | |
| C8 | 0.35288 (18) | 0.8950 (6) | −0.0835 (2) | 0.0759 (11) | |
| H8 | 0.3544 | 0.9178 | −0.1429 | 0.091* | |
| C9 | 0.29577 (17) | 0.8083 (6) | −0.0720 (3) | 0.0946 (14) | |
| H9A | 0.2646 | 0.7756 | −0.1228 | 0.114* | |
| H9B | 0.2995 | 0.7282 | −0.0242 | 0.114* | |
| C10 | 0.30497 (19) | 0.9911 (6) | −0.0532 (3) | 0.0912 (13) | |
| H10A | 0.3144 | 1.0262 | 0.0064 | 0.109* | |
| H10B | 0.2795 | 1.0735 | −0.0922 | 0.109* | |
| C11 | 0.63187 (18) | 0.6133 (5) | 0.2889 (3) | 0.0874 (13) | |
| H11A | 0.6403 | 0.4911 | 0.2835 | 0.131* | |
| H11B | 0.6271 | 0.6368 | 0.3458 | 0.131* | |
| H11C | 0.6662 | 0.6810 | 0.2779 | 0.131* | |
| C12 | 0.37396 (16) | 1.0796 (4) | 0.2087 (2) | 0.0510 (8) | |
| H1 | 0.4126 (16) | 0.857 (4) | 0.0285 (8) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Co1 | 0.0370 (3) | 0.0611 (4) | 0.0314 (3) | 0.000 | 0.0029 (2) | 0.000 |
| N1 | 0.0502 (16) | 0.0656 (18) | 0.0380 (14) | −0.0084 (13) | 0.0025 (13) | 0.0051 (13) |
| N2 | 0.0484 (16) | 0.0724 (19) | 0.0538 (16) | 0.0111 (14) | 0.0109 (13) | −0.0032 (14) |
| O1 | 0.0378 (11) | 0.0764 (14) | 0.0359 (11) | 0.0060 (10) | 0.0045 (9) | −0.0060 (10) |
| O2 | 0.0489 (13) | 0.0754 (16) | 0.0477 (13) | 0.0137 (11) | 0.0003 (10) | 0.0001 (11) |
| S1 | 0.0532 (6) | 0.0992 (8) | 0.0930 (8) | 0.0165 (5) | −0.0054 (5) | 0.0037 (6) |
| C1 | 0.0559 (19) | 0.0499 (19) | 0.0434 (18) | −0.0123 (15) | 0.0151 (15) | −0.0048 (14) |
| C2 | 0.0393 (16) | 0.0477 (18) | 0.0439 (17) | −0.0078 (13) | 0.0094 (13) | −0.0066 (14) |
| C3 | 0.0420 (18) | 0.0489 (18) | 0.0534 (19) | −0.0044 (13) | 0.0085 (15) | −0.0040 (14) |
| C4 | 0.0458 (19) | 0.062 (2) | 0.079 (3) | 0.0045 (16) | 0.0149 (18) | −0.0026 (18) |
| C5 | 0.061 (2) | 0.075 (3) | 0.087 (3) | −0.0018 (19) | 0.040 (2) | −0.012 (2) |
| C6 | 0.069 (2) | 0.071 (2) | 0.056 (2) | −0.0079 (19) | 0.0313 (19) | −0.0101 (17) |
| C7 | 0.062 (2) | 0.062 (2) | 0.0357 (17) | −0.0158 (17) | 0.0126 (16) | −0.0028 (15) |
| C8 | 0.059 (2) | 0.118 (3) | 0.0442 (19) | −0.004 (2) | 0.0002 (17) | 0.012 (2) |
| C9 | 0.051 (2) | 0.090 (3) | 0.131 (4) | −0.004 (2) | −0.006 (2) | 0.001 (3) |
| C10 | 0.076 (3) | 0.081 (3) | 0.104 (3) | 0.019 (2) | −0.006 (2) | 0.010 (3) |
| C11 | 0.069 (3) | 0.112 (3) | 0.069 (3) | 0.035 (2) | −0.009 (2) | 0.014 (2) |
| C12 | 0.059 (2) | 0.0513 (19) | 0.0439 (18) | 0.0003 (16) | 0.0133 (15) | −0.0017 (15) |
| Co1—O1i | 1.997 (2) | C3—C4 | 1.371 (4) |
| Co1—O1 | 1.997 (2) | C4—C5 | 1.389 (5) |
| Co1—N2i | 2.031 (3) | C4—H4 | 0.9300 |
| Co1—N2 | 2.031 (3) | C5—C6 | 1.350 (5) |
| Co1—O2 | 2.387 (2) | C5—H5 | 0.9300 |
| Co1—O2i | 2.387 (2) | C6—H6 | 0.9300 |
| N1—C7 | 1.283 (4) | C7—H7 | 0.9300 |
| N1—C8 | 1.434 (4) | C8—C10 | 1.451 (5) |
| N1—H1 | 0.901 (10) | C8—C9 | 1.461 (5) |
| N2—C12 | 1.157 (4) | C8—H8 | 0.9800 |
| O1—C2 | 1.308 (3) | C9—C10 | 1.434 (6) |
| O2—C3 | 1.375 (4) | C9—H9A | 0.9700 |
| O2—C11 | 1.428 (4) | C9—H9B | 0.9700 |
| S1—C12 | 1.615 (4) | C10—H10A | 0.9700 |
| C1—C6 | 1.408 (4) | C10—H10B | 0.9700 |
| C1—C2 | 1.412 (4) | C11—H11A | 0.9600 |
| C1—C7 | 1.416 (4) | C11—H11B | 0.9600 |
| C2—C3 | 1.409 (4) | C11—H11C | 0.9600 |
| O1i—Co1—O1 | 148.34 (13) | C6—C5—C4 | 120.7 (3) |
| O1i—Co1—N2i | 92.76 (9) | C6—C5—H5 | 119.6 |
| O1—Co1—N2i | 106.91 (9) | C4—C5—H5 | 119.6 |
| O1i—Co1—N2 | 106.91 (9) | C5—C6—C1 | 120.3 (3) |
| O1—Co1—N2 | 92.76 (9) | C5—C6—H6 | 119.9 |
| N2i—Co1—N2 | 103.17 (16) | C1—C6—H6 | 119.9 |
| O1i—Co1—O2 | 86.55 (8) | N1—C7—C1 | 124.3 (3) |
| O1—Co1—O2 | 71.97 (8) | N1—C7—H7 | 117.8 |
| N2i—Co1—O2 | 82.96 (10) | C1—C7—H7 | 117.8 |
| N2—Co1—O2 | 164.69 (9) | N1—C8—C10 | 121.6 (3) |
| O1i—Co1—O2i | 71.97 (8) | N1—C8—C9 | 119.4 (3) |
| O1—Co1—O2i | 86.55 (8) | C10—C8—C9 | 59.0 (3) |
| N2i—Co1—O2i | 164.69 (9) | N1—C8—H8 | 115.1 |
| N2—Co1—O2i | 82.96 (10) | C10—C8—H8 | 115.1 |
| O2—Co1—O2i | 94.69 (11) | C9—C8—H8 | 115.1 |
| C7—N1—C8 | 124.7 (3) | C10—C9—C8 | 60.1 (3) |
| C7—N1—H1 | 120 (2) | C10—C9—H9A | 117.8 |
| C8—N1—H1 | 115 (2) | C8—C9—H9A | 117.8 |
| C12—N2—Co1 | 155.4 (3) | C10—C9—H9B | 117.8 |
| C2—O1—Co1 | 119.80 (17) | C8—C9—H9B | 117.8 |
| C3—O2—C11 | 117.7 (3) | H9A—C9—H9B | 114.9 |
| C3—O2—Co1 | 107.81 (17) | C9—C10—C8 | 60.9 (3) |
| C11—O2—Co1 | 126.1 (2) | C9—C10—H10A | 117.7 |
| C6—C1—C2 | 120.1 (3) | C8—C10—H10A | 117.7 |
| C6—C1—C7 | 119.7 (3) | C9—C10—H10B | 117.7 |
| C2—C1—C7 | 120.2 (3) | C8—C10—H10B | 117.7 |
| O1—C2—C3 | 120.2 (3) | H10A—C10—H10B | 114.8 |
| O1—C2—C1 | 122.3 (3) | O2—C11—H11A | 109.5 |
| C3—C2—C1 | 117.5 (3) | O2—C11—H11B | 109.5 |
| C4—C3—O2 | 126.6 (3) | H11A—C11—H11B | 109.5 |
| C4—C3—C2 | 121.0 (3) | O2—C11—H11C | 109.5 |
| O2—C3—C2 | 112.3 (3) | H11A—C11—H11C | 109.5 |
| C3—C4—C5 | 120.3 (3) | H11B—C11—H11C | 109.5 |
| C3—C4—H4 | 119.8 | N2—C12—S1 | 178.3 (3) |
| C5—C4—H4 | 119.8 |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.901 (10) | 1.93 (3) | 2.609 (3) | 131 (3) |
| Co1—O1 | 1.997 (2) | Co1—O2 | 2.387 (2) |
| Co1—N2 | 2.031 (3) | ||
| O1i—Co1—O1 | 148.34 (13) | O1i—Co1—O2 | 86.55 (8) |
| O1i—Co1—N2 | 106.91 (9) | O1—Co1—O2 | 71.97 (8) |
| O1—Co1—N2 | 92.76 (9) | N2i—Co1—O2 | 82.96 (10) |
| N2i—Co1—N2 | 103.17 (16) | N2—Co1—O2 | 164.69 (9) |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.901 (10) | 1.93 (3) | 2.609 (3) | 131 (3) |
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Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
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Schiff base complexes have been studied extensively due to their interesting structures and numerous applications (Mukhopadhyay et al., 2003; Kraihanzel et al., 1981; Di Bella et al., 1997; Loeb et al., 1984). Previously, the author has reported the crystal structure of a Schiff base zinc(II) complex (Wang, 2007a) and a Schiff base nickel(II) complex (Wang, 2007b). As part of a further investigation of Schiff base complexes, the structure of the title compound, a mononuclear cobalt(II) complex, is reported here.
The octahedral coordination environment of CoII atom in the title compound is formed by four O atoms from two Schiff base ligands, and by two N atoms from two thiocyanate ligands (Fig. 1). The central Co atom lies on a twofold axis symmetry position.The coordination bond distances and angles are listed in Table 1.