Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105016811/fr1521sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105016811/fr1521Isup2.hkl |
CCDC reference: 278542
An ethanol solution of 2-aminobenzothiazole (4 mmol in 10 ml of ethanol) was added dropwise to Co(CH3COO)2·6H2O (2 mmol in 5 ml of ethanol) with stirring. The colour of the solution changed immediately to violet. The mixture was refluxed for 2 h and the resulting solution was kept at room temperature. After several days, violet crystals were obtained and dried under vacuum.
All H atoms were placed in calculated positions, with C—H distances of 0.93 and 0.96 Å, and N—H distances of 0.86 Å. The Uiso(H) values were constrained to be 1.2 (1.5 for methyl groups) times Ueq of the carrier atom.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELX86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Co(C2H3O2)2(C7H6N2S)2] | F(000) = 980 |
Mr = 477.43 | Dx = 1.563 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 22768 reflections |
a = 8.3049 (4) Å | θ = 1.5–26.2° |
b = 27.1833 (16) Å | µ = 1.09 mm−1 |
c = 8.9868 (5) Å | T = 100 K |
V = 2028.81 (19) Å3 | Prism, violet |
Z = 4 | 0.29 × 0.18 × 0.11 mm |
Stoe IPDS-II diffractometer | 3861 independent reflections |
Radiation source: fine-focus sealed tube | 3697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.1°, θmin = 1.5° |
ϕ or ω? scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie 2002) | k = −33→33 |
Tmin = 0.613, Tmax = 0.830 | l = −9→11 |
23485 measured reflections |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3861 reflections | Δρmax = 0.22 e Å−3 |
264 parameters | Δρmin = −0.50 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1720 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.005 (10) |
[Co(C2H3O2)2(C7H6N2S)2] | V = 2028.81 (19) Å3 |
Mr = 477.43 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 8.3049 (4) Å | µ = 1.09 mm−1 |
b = 27.1833 (16) Å | T = 100 K |
c = 8.9868 (5) Å | 0.29 × 0.18 × 0.11 mm |
Stoe IPDS-II diffractometer | 3861 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie 2002) | 3697 reflections with I > 2σ(I) |
Tmin = 0.613, Tmax = 0.830 | Rint = 0.054 |
23485 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.063 | Δρmax = 0.22 e Å−3 |
S = 1.04 | Δρmin = −0.50 e Å−3 |
3861 reflections | Absolute structure: Flack (1983), 1720 Friedel pairs |
264 parameters | Absolute structure parameter: −0.005 (10) |
1 restraint |
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 | 0.13575 (3) | 0.122036 (8) | 1.03477 (4) | 0.01848 (8) | |
S1 | 0.27466 (7) | 0.273666 (19) | 0.85372 (7) | 0.02730 (13) | |
S2 | 0.22983 (7) | −0.021294 (18) | 0.77564 (7) | 0.02657 (13) | |
O1 | −0.10194 (17) | 0.10978 (5) | 1.0401 (2) | 0.0224 (3) | |
O2 | −0.05469 (18) | 0.17762 (5) | 1.16565 (19) | 0.0232 (3) | |
O3 | 0.28953 (18) | 0.12872 (5) | 1.20415 (19) | 0.0211 (3) | |
O4 | 0.13515 (18) | 0.06757 (6) | 1.2751 (2) | 0.0294 (4) | |
N1 | 0.1939 (2) | 0.18368 (6) | 0.9143 (2) | 0.0196 (4) | |
N2 | 0.3103 (2) | 0.22725 (6) | 1.1131 (2) | 0.0251 (4) | |
H2A | 0.3032 | 0.2025 | 1.1725 | 0.030* | |
H2B | 0.3512 | 0.2545 | 1.1439 | 0.030* | |
N3 | 0.2146 (2) | 0.06406 (6) | 0.9070 (2) | 0.0212 (4) | |
N4 | −0.0177 (2) | 0.01509 (6) | 0.9285 (3) | 0.0286 (4) | |
H4A | −0.0666 | 0.0368 | 0.9815 | 0.034* | |
H4B | −0.0650 | −0.0121 | 0.9067 | 0.034* | |
C1 | 0.2585 (2) | 0.22337 (7) | 0.9743 (3) | 0.0210 (4) | |
C2 | 0.1520 (2) | 0.19150 (8) | 0.7663 (3) | 0.0214 (4) | |
C3 | 0.0762 (3) | 0.15796 (8) | 0.6729 (3) | 0.0255 (5) | |
H3 | 0.0510 | 0.1265 | 0.7066 | 0.031* | |
C4 | 0.0388 (3) | 0.17197 (8) | 0.5290 (3) | 0.0319 (5) | |
H4 | −0.0116 | 0.1497 | 0.4659 | 0.038* | |
C5 | 0.0755 (3) | 0.21912 (10) | 0.4768 (3) | 0.0361 (6) | |
H5 | 0.0496 | 0.2278 | 0.3796 | 0.043* | |
C6 | 0.1499 (3) | 0.25282 (10) | 0.5688 (3) | 0.0348 (6) | |
H6 | 0.1744 | 0.2842 | 0.5347 | 0.042* | |
C7 | 0.1874 (3) | 0.23885 (9) | 0.7131 (3) | 0.0272 (5) | |
C8 | 0.1304 (2) | 0.02359 (8) | 0.8803 (3) | 0.0222 (5) | |
C9 | 0.3672 (2) | 0.06120 (8) | 0.8395 (3) | 0.0220 (4) | |
C10 | 0.4843 (3) | 0.09785 (8) | 0.8408 (3) | 0.0253 (5) | |
H10 | 0.4655 | 0.1276 | 0.8886 | 0.030* | |
C11 | 0.6294 (3) | 0.08907 (9) | 0.7696 (3) | 0.0289 (5) | |
H11 | 0.7088 | 0.1132 | 0.7706 | 0.035* | |
C12 | 0.6585 (3) | 0.04482 (9) | 0.6967 (3) | 0.0313 (5) | |
H12 | 0.7572 | 0.0397 | 0.6502 | 0.038* | |
C13 | 0.5427 (3) | 0.00831 (9) | 0.6924 (3) | 0.0286 (5) | |
H13 | 0.5611 | −0.0211 | 0.6425 | 0.034* | |
C14 | 0.3974 (3) | 0.01707 (8) | 0.7651 (3) | 0.0232 (4) | |
C15 | −0.1500 (2) | 0.14469 (7) | 1.1248 (3) | 0.0200 (4) | |
C16 | −0.3214 (3) | 0.14501 (9) | 1.1767 (3) | 0.0286 (5) | |
H16A | −0.3703 | 0.1759 | 1.1514 | 0.043* | |
H16B | −0.3245 | 0.1406 | 1.2826 | 0.043* | |
H16C | −0.3793 | 0.1187 | 1.1293 | 0.043* | |
C17 | 0.2499 (2) | 0.09582 (7) | 1.2998 (3) | 0.0217 (5) | |
C18 | 0.3489 (3) | 0.09268 (10) | 1.4375 (3) | 0.0337 (6) | |
H18A | 0.4478 | 0.0758 | 1.4161 | 0.051* | |
H18B | 0.2905 | 0.0749 | 1.5125 | 0.051* | |
H18C | 0.3722 | 0.1252 | 1.4729 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.02036 (13) | 0.01315 (12) | 0.02192 (15) | −0.00042 (9) | −0.00199 (12) | −0.00190 (12) |
S1 | 0.0356 (3) | 0.0210 (3) | 0.0253 (3) | −0.0074 (2) | −0.0037 (2) | 0.0063 (2) |
S2 | 0.0343 (3) | 0.0167 (2) | 0.0286 (3) | 0.0035 (2) | −0.0024 (3) | −0.0059 (2) |
O1 | 0.0252 (7) | 0.0162 (6) | 0.0259 (8) | 0.0010 (5) | −0.0001 (8) | −0.0016 (8) |
O2 | 0.0249 (8) | 0.0190 (7) | 0.0257 (9) | −0.0012 (6) | −0.0020 (6) | −0.0026 (6) |
O3 | 0.0235 (7) | 0.0168 (7) | 0.0229 (8) | 0.0007 (5) | −0.0004 (6) | 0.0028 (6) |
O4 | 0.0254 (8) | 0.0183 (7) | 0.0445 (11) | −0.0036 (6) | 0.0007 (7) | 0.0046 (8) |
N1 | 0.0231 (9) | 0.0166 (8) | 0.0189 (10) | −0.0011 (6) | 0.0000 (7) | −0.0017 (7) |
N2 | 0.0363 (10) | 0.0149 (8) | 0.0240 (11) | −0.0063 (7) | −0.0065 (9) | 0.0011 (8) |
N3 | 0.0229 (9) | 0.0179 (8) | 0.0227 (10) | −0.0007 (7) | −0.0010 (7) | −0.0022 (7) |
N4 | 0.0277 (9) | 0.0189 (8) | 0.0392 (13) | −0.0059 (7) | 0.0011 (9) | −0.0086 (8) |
C1 | 0.0228 (10) | 0.0168 (9) | 0.0235 (12) | −0.0001 (8) | 0.0009 (9) | −0.0009 (8) |
C2 | 0.0231 (10) | 0.0207 (10) | 0.0203 (12) | 0.0027 (8) | 0.0008 (8) | −0.0003 (9) |
C3 | 0.0268 (11) | 0.0229 (10) | 0.0267 (14) | 0.0028 (9) | −0.0039 (9) | −0.0055 (9) |
C4 | 0.0319 (11) | 0.0379 (11) | 0.0259 (13) | 0.0058 (9) | −0.0053 (12) | −0.0081 (12) |
C5 | 0.0409 (14) | 0.0453 (14) | 0.0221 (13) | 0.0026 (11) | −0.0043 (11) | 0.0007 (10) |
C6 | 0.0411 (14) | 0.0373 (13) | 0.0262 (18) | −0.0032 (11) | −0.0027 (10) | 0.0091 (9) |
C7 | 0.0282 (11) | 0.0284 (12) | 0.0249 (13) | −0.0014 (9) | 0.0009 (10) | 0.0026 (9) |
C8 | 0.0285 (11) | 0.0174 (10) | 0.0207 (13) | 0.0014 (8) | −0.0044 (9) | −0.0037 (8) |
C9 | 0.0239 (11) | 0.0212 (10) | 0.0211 (12) | 0.0054 (8) | −0.0014 (8) | 0.0010 (9) |
C10 | 0.0261 (10) | 0.0235 (10) | 0.0263 (12) | 0.0004 (9) | −0.0027 (9) | −0.0033 (9) |
C11 | 0.0247 (11) | 0.0337 (12) | 0.0285 (13) | 0.0018 (9) | −0.0011 (10) | −0.0039 (11) |
C12 | 0.0258 (11) | 0.0400 (14) | 0.0281 (14) | 0.0100 (10) | 0.0008 (10) | −0.0024 (11) |
C13 | 0.0330 (13) | 0.0280 (11) | 0.0247 (13) | 0.0125 (9) | −0.0018 (10) | −0.0035 (9) |
C14 | 0.0297 (11) | 0.0215 (10) | 0.0183 (12) | 0.0042 (8) | −0.0036 (9) | −0.0017 (9) |
C15 | 0.0250 (10) | 0.0166 (9) | 0.0184 (12) | 0.0042 (8) | −0.0027 (9) | 0.0015 (8) |
C16 | 0.0207 (10) | 0.0287 (12) | 0.0363 (15) | 0.0009 (9) | 0.0041 (10) | 0.0014 (10) |
C17 | 0.0224 (10) | 0.0171 (9) | 0.0255 (13) | 0.0051 (8) | 0.0027 (9) | 0.0012 (8) |
C18 | 0.0356 (13) | 0.0395 (13) | 0.0261 (14) | 0.0100 (10) | −0.0026 (10) | 0.0058 (11) |
Co1—O3 | 1.9953 (16) | C3—H3 | 0.9300 |
Co1—O1 | 2.0025 (14) | C4—C5 | 1.398 (4) |
Co1—N1 | 2.0524 (18) | C4—H4 | 0.9300 |
Co1—N3 | 2.0568 (18) | C5—C6 | 1.380 (4) |
S1—C7 | 1.737 (3) | C5—H5 | 0.9300 |
S1—C1 | 1.750 (2) | C6—C7 | 1.387 (4) |
S2—C14 | 1.742 (2) | C6—H6 | 0.9300 |
S2—C8 | 1.748 (2) | C9—C10 | 1.392 (3) |
O1—C15 | 1.280 (3) | C9—C14 | 1.396 (3) |
O2—C15 | 1.250 (3) | C10—C11 | 1.385 (3) |
O3—C17 | 1.283 (3) | C10—H10 | 0.9300 |
O4—C17 | 1.244 (3) | C11—C12 | 1.391 (4) |
N1—C1 | 1.320 (3) | C11—H11 | 0.9300 |
N1—C2 | 1.391 (3) | C12—C13 | 1.383 (4) |
N2—C1 | 1.324 (3) | C12—H12 | 0.9300 |
N2—H2A | 0.8600 | C13—C14 | 1.393 (3) |
N2—H2B | 0.8600 | C13—H13 | 0.9300 |
N3—C8 | 1.325 (3) | C15—C16 | 1.498 (3) |
N3—C9 | 1.408 (3) | C16—H16A | 0.9600 |
N4—C8 | 1.325 (3) | C16—H16B | 0.9600 |
N4—H4A | 0.8600 | C16—H16C | 0.9600 |
N4—H4B | 0.8600 | C17—C18 | 1.489 (3) |
C2—C3 | 1.390 (3) | C18—H18A | 0.9600 |
C2—C7 | 1.404 (3) | C18—H18B | 0.9600 |
C3—C4 | 1.383 (4) | C18—H18C | 0.9600 |
O3—Co1—O1 | 128.90 (7) | C6—C7—S1 | 128.7 (2) |
O3—Co1—N1 | 100.22 (7) | C2—C7—S1 | 109.80 (18) |
O1—Co1—N1 | 112.35 (7) | N4—C8—N3 | 125.1 (2) |
O3—Co1—N3 | 106.97 (7) | N4—C8—S2 | 119.52 (16) |
O1—Co1—N3 | 101.51 (7) | N3—C8—S2 | 115.34 (16) |
N1—Co1—N3 | 104.86 (8) | C10—C9—C14 | 119.6 (2) |
C7—S1—C1 | 89.59 (11) | C10—C9—N3 | 125.9 (2) |
C14—S2—C8 | 89.35 (10) | C14—C9—N3 | 114.6 (2) |
C15—O1—Co1 | 101.42 (13) | C11—C10—C9 | 118.7 (2) |
C17—O3—Co1 | 106.45 (13) | C11—C10—H10 | 120.6 |
C1—N1—C2 | 111.53 (19) | C9—C10—H10 | 120.6 |
C1—N1—Co1 | 123.21 (16) | C10—C11—C12 | 121.2 (2) |
C2—N1—Co1 | 124.76 (14) | C10—C11—H11 | 119.4 |
C1—N2—H2A | 120.0 | C12—C11—H11 | 119.4 |
C1—N2—H2B | 120.0 | C13—C12—C11 | 120.8 (2) |
H2A—N2—H2B | 120.0 | C13—C12—H12 | 119.6 |
C8—N3—C9 | 110.55 (19) | C11—C12—H12 | 119.6 |
C8—N3—Co1 | 124.70 (15) | C12—C13—C14 | 117.8 (2) |
C9—N3—Co1 | 124.72 (14) | C12—C13—H13 | 121.1 |
C8—N4—H4A | 120.0 | C14—C13—H13 | 121.1 |
C8—N4—H4B | 120.0 | C13—C14—C9 | 121.8 (2) |
H4A—N4—H4B | 120.0 | C13—C14—S2 | 127.97 (18) |
N1—C1—N2 | 125.6 (2) | C9—C14—S2 | 110.19 (17) |
N1—C1—S1 | 114.64 (18) | O2—C15—O1 | 120.54 (19) |
N2—C1—S1 | 119.77 (16) | O2—C15—C16 | 120.4 (2) |
C3—C2—N1 | 126.2 (2) | O1—C15—C16 | 119.05 (19) |
C3—C2—C7 | 119.3 (2) | C15—C16—H16A | 109.5 |
N1—C2—C7 | 114.4 (2) | C15—C16—H16B | 109.5 |
C4—C3—C2 | 119.1 (2) | H16A—C16—H16B | 109.5 |
C4—C3—H3 | 120.5 | C15—C16—H16C | 109.5 |
C2—C3—H3 | 120.5 | H16A—C16—H16C | 109.5 |
C3—C4—C5 | 121.1 (2) | H16B—C16—H16C | 109.5 |
C3—C4—H4 | 119.4 | O4—C17—O3 | 120.5 (2) |
C5—C4—H4 | 119.4 | O4—C17—C18 | 122.4 (2) |
C6—C5—C4 | 120.3 (3) | O3—C17—C18 | 117.1 (2) |
C6—C5—H5 | 119.8 | C17—C18—H18A | 109.5 |
C4—C5—H5 | 119.8 | C17—C18—H18B | 109.5 |
C5—C6—C7 | 118.6 (2) | H18A—C18—H18B | 109.5 |
C5—C6—H6 | 120.7 | C17—C18—H18C | 109.5 |
C7—C6—H6 | 120.7 | H18A—C18—H18C | 109.5 |
C6—C7—C2 | 121.5 (2) | H18B—C18—H18C | 109.5 |
O3—Co1—O1—C15 | 54.22 (16) | C5—C6—C7—S1 | −177.9 (2) |
N1—Co1—O1—C15 | −71.10 (16) | C3—C2—C7—C6 | −0.6 (4) |
N3—Co1—O1—C15 | 177.39 (14) | N1—C2—C7—C6 | −178.6 (2) |
O1—Co1—O3—C17 | 41.08 (15) | C3—C2—C7—S1 | 177.85 (17) |
N1—Co1—O3—C17 | 171.01 (13) | N1—C2—C7—S1 | −0.1 (3) |
N3—Co1—O3—C17 | −79.88 (14) | C1—S1—C7—C6 | 178.3 (2) |
O3—Co1—N1—C1 | −25.49 (18) | C1—S1—C7—C2 | −0.10 (18) |
O1—Co1—N1—C1 | 114.33 (17) | C9—N3—C8—N4 | −179.9 (2) |
N3—Co1—N1—C1 | −136.26 (17) | Co1—N3—C8—N4 | 1.9 (3) |
O3—Co1—N1—C2 | 163.28 (16) | C9—N3—C8—S2 | 1.3 (3) |
O1—Co1—N1—C2 | −56.90 (18) | Co1—N3—C8—S2 | −176.97 (11) |
N3—Co1—N1—C2 | 52.51 (18) | C14—S2—C8—N4 | −179.3 (2) |
O3—Co1—N3—C8 | 119.32 (18) | C14—S2—C8—N3 | −0.40 (18) |
O1—Co1—N3—C8 | −17.8 (2) | C8—N3—C9—C10 | 177.8 (2) |
N1—Co1—N3—C8 | −134.85 (18) | Co1—N3—C9—C10 | −4.0 (3) |
O3—Co1—N3—C9 | −58.67 (19) | C8—N3—C9—C14 | −1.7 (3) |
O1—Co1—N3—C9 | 164.26 (18) | Co1—N3—C9—C14 | 176.49 (16) |
N1—Co1—N3—C9 | 47.16 (19) | C14—C9—C10—C11 | −1.0 (4) |
C2—N1—C1—N2 | −180.0 (2) | N3—C9—C10—C11 | 179.5 (2) |
Co1—N1—C1—N2 | 7.8 (3) | C9—C10—C11—C12 | 0.5 (4) |
C2—N1—C1—S1 | −0.4 (2) | C10—C11—C12—C13 | 0.4 (4) |
Co1—N1—C1—S1 | −172.64 (10) | C11—C12—C13—C14 | −0.9 (4) |
C7—S1—C1—N1 | 0.28 (18) | C12—C13—C14—C9 | 0.5 (4) |
C7—S1—C1—N2 | 179.89 (19) | C12—C13—C14—S2 | 178.78 (19) |
C1—N1—C2—C3 | −177.5 (2) | C10—C9—C14—C13 | 0.4 (4) |
Co1—N1—C2—C3 | −5.4 (3) | N3—C9—C14—C13 | −180.0 (2) |
C1—N1—C2—C7 | 0.3 (3) | C10—C9—C14—S2 | −178.12 (18) |
Co1—N1—C2—C7 | 172.42 (15) | N3—C9—C14—S2 | 1.4 (3) |
N1—C2—C3—C4 | 178.3 (2) | C8—S2—C14—C13 | −179.0 (2) |
C7—C2—C3—C4 | 0.6 (3) | C8—S2—C14—C9 | −0.59 (18) |
C2—C3—C4—C5 | −0.2 (3) | Co1—O1—C15—O2 | 7.5 (2) |
C3—C4—C5—C6 | −0.2 (4) | Co1—O1—C15—C16 | −171.31 (17) |
C4—C5—C6—C7 | 0.1 (4) | Co1—O3—C17—O4 | 0.5 (2) |
C5—C6—C7—C2 | 0.3 (4) | Co1—O3—C17—C18 | 179.22 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.86 | 2.03 | 2.806 (2) | 150 |
N2—H2B···O2i | 0.86 | 2.01 | 2.857 (2) | 167 |
N4—H4A···O1 | 0.86 | 2.07 | 2.850 (2) | 150 |
N4—H4B···O4ii | 0.86 | 2.00 | 2.811 (3) | 156 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C2H3O2)2(C7H6N2S)2] |
Mr | 477.43 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 100 |
a, b, c (Å) | 8.3049 (4), 27.1833 (16), 8.9868 (5) |
V (Å3) | 2028.81 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.09 |
Crystal size (mm) | 0.29 × 0.18 × 0.11 |
Data collection | |
Diffractometer | Stoe IPDS-II diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie 2002) |
Tmin, Tmax | 0.613, 0.830 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23485, 3861, 3697 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.063, 1.04 |
No. of reflections | 3861 |
No. of parameters | 264 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.50 |
Absolute structure | Flack (1983), 1720 Friedel pairs |
Absolute structure parameter | −0.005 (10) |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELX86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Co1—O3 | 1.9953 (16) | O4—C17 | 1.244 (3) |
Co1—O1 | 2.0025 (14) | N1—C1 | 1.320 (3) |
Co1—N1 | 2.0524 (18) | N1—C2 | 1.391 (3) |
Co1—N3 | 2.0568 (18) | N2—C1 | 1.324 (3) |
O1—C15 | 1.280 (3) | N3—C8 | 1.325 (3) |
O2—C15 | 1.250 (3) | N3—C9 | 1.408 (3) |
O3—C17 | 1.283 (3) | N4—C8 | 1.325 (3) |
Co1—N1—C1—N2 | 7.8 (3) | Co1—O1—C15—C16 | −171.31 (17) |
Co1—N3—C8—N4 | 1.9 (3) | Co1—O3—C17—C18 | 179.22 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.86 | 2.03 | 2.806 (2) | 150 |
N2—H2B···O2i | 0.86 | 2.01 | 2.857 (2) | 167 |
N4—H4A···O1 | 0.86 | 2.07 | 2.850 (2) | 150 |
N4—H4B···O4ii | 0.86 | 2.00 | 2.811 (3) | 156 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x, −y, z−1/2. |
Small and simple heterocyclic structures often exhibit complex biological properties. Substituted benzothiazoles show antitumour (Goldfarb et al., 1999), anti-infective and antifungal (Sener et al., 2000), and antihelmintic activities (Nadkarn et al., 2000). Bis(benzothiazole) compounds have been studied as potential mimics for metalloproteins (Thompson et al., 1982). It is well known that N and S atoms play a key role in the coordination of metals at the active sites of numerous metallobiomolecules (Karlin & Zubieta, 1983). The structures of many metal complexes of 2-amino-1,3-thiazole derivatives, where the metal is directly bound to the ligand, are known, and these complexes include most of the first-row transition metals (i.e. Mn–Zn). In all but a few cases, the thiazole moities bind to the metal via endocylic N atoms (Lynch & Duckhouse, 2001; Usman et al., 2003). We report here the X-ray crystal structure of the title compound, (I).
In the molecular structure of (I) (Fig.1), the two benzothiazole moieties form a dihedral angle of 77.86 (3)°. It is noteworthy that the two amine groups are not both located on the same side, because of the steric hindrance. Both benzothiazole moieties are nearly planar, the largest deviation from the plane being that of atom C2 [−0.026 (1) Å]. The cobalt centre, coordinated by two endocylic N atoms from the thiazole moieties and two acetate ligands, –CoNCN– and –CoOCC, adopts a syn-periplanar and an anti-periplanar conformation, respectively. This CoN2O2 coordination forms a slightly distorted tetrahedral geometry, the angles around the Co atom ranging from 100.22 (7) to 128.90 (7)°. The bond lengths and angles in (I) are shown in Table 1. The C1—N1, C1—N2, C8—N3 and C8—N4 bonds are somewhat shorter than the C2—N1 and C9—N3 bonds, as a result of pronounced delocalization in the –N—C═N– fragment of the 2-aminobenzothiazole ring. The amine groups of both thiazole ligands are hydrogen bonded to the O atoms of the acetate ligands by intra- and intermolecular hydrogen bonds (Table 2). The N2—H2B···O2 hydrogen bonds interconnect the molecules into chains along the a direction, and these are further interconnected into a three-dimensional network by N4—H4B···O4 hydrogen bonds (Fig. 2).