Acta Cryst. (2009). E65, o37 [ doi:10.1107/S1600536808040658 ]
In the molecular structure of the title compound, C13H12N2O4S2, there is a dihedral angle of 0.41 (13)° between the benzene and thiazole rings. In the crystal, inversion dimers linked by two C-H
O interactions together with ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking between the parallel benzene rings of adjacent molecules [centroid-centroid distance = 3.673 (2) Å].
A solution of (Z)-methyl-4-bromo-2-(methoxyimino)-3-oxobutanoate 30 ml (2.38 g, 0.01 mol) in methanol (10 ml) was added dropwise to a stirred solution of benzothiazole-2-thiol (1.67 g, 0.01 mol) and sodium hydroxide (0.40 g, 0.01 mol) in water (25 ml). The resulting mixture was stirred at room temperature for 3 h, the mixture was filtered and the residue was dissolved in 30 ml e thanol, Single crystals of (I) were obtained after several days.
H atoms were placed in calculated positions with C—H = 0.93–0.97 Å, and refined in riding mode with Uiso(H) = 1.2–1.5 Ueq(C).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./at2688fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C13H12N2O4S2 | Z = 2 |
| Mr = 324.39 | F(000) = 336 |
| Triclinic, P1 | Dx = 1.419 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.019 (3) Å | Cell parameters from 2679 reflections |
| b = 10.037 (4) Å | θ = 2.1–25.0° |
| c = 10.662 (5) Å | µ = 0.37 mm−1 |
| α = 76.44 (2)° | T = 293 K |
| β = 67.997 (14)° | Block, colourless |
| γ = 74.964 (15)° | 0.22 × 0.19 × 0.18 mm |
| V = 759.3 (6) Å3 |
| Bruker SMART CCD area-detector diffractometer | 2620 independent reflections |
| Radiation source: fine-focus sealed tube | 2278 reflections with I > 2σ(I) |
| graphite | Rint = 0.020 |
| φ and ω scans | θmax = 25.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
| Tmin = 0.913, Tmax = 0.939 | k = −11→11 |
| 7739 measured reflections | l = −12→12 |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.101 | H-atom parameters constrained |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1857P] where P = (Fo2 + 2Fc2)/3 |
| 2620 reflections | (Δ/σ)max < 0.001 |
| 190 parameters | Δρmax = 0.23 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
| C13H12N2O4S2 | γ = 74.964 (15)° |
| Mr = 324.39 | V = 759.3 (6) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.019 (3) Å | Mo Kα radiation |
| b = 10.037 (4) Å | µ = 0.37 mm−1 |
| c = 10.662 (5) Å | T = 293 K |
| α = 76.44 (2)° | 0.22 × 0.19 × 0.18 mm |
| β = 67.997 (14)° |
| Bruker SMART CCD area-detector diffractometer | 2620 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2278 reflections with I > 2σ(I) |
| Tmin = 0.913, Tmax = 0.939 | Rint = 0.020 |
| 7739 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.101 | Δρmax = 0.23 e Å−3 |
| S = 1.10 | Δρmin = −0.26 e Å−3 |
| 2620 reflections | Absolute structure: ? |
| 190 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| C1 | 0.2301 (4) | 0.0381 (3) | 0.4741 (3) | 0.0665 (7) | |
| H1 | 0.1206 | 0.0298 | 0.5455 | 0.080* | |
| C2 | 0.3264 (5) | −0.0698 (2) | 0.3972 (3) | 0.0788 (9) | |
| H2 | 0.2803 | −0.1514 | 0.4185 | 0.095* | |
| C3 | 0.4890 (4) | −0.0581 (3) | 0.2898 (3) | 0.0735 (8) | |
| H3 | 0.5497 | −0.1320 | 0.2407 | 0.088* | |
| C4 | 0.5617 (4) | 0.0593 (3) | 0.2549 (3) | 0.0635 (6) | |
| H4 | 0.6707 | 0.0670 | 0.1829 | 0.076* | |
| C5 | 0.4664 (3) | 0.1679 (2) | 0.3314 (2) | 0.0472 (5) | |
| C6 | 0.3029 (3) | 0.1583 (2) | 0.4407 (2) | 0.0452 (5) | |
| C7 | 0.3251 (3) | 0.3681 (2) | 0.45184 (18) | 0.0387 (4) | |
| C8 | 0.0771 (3) | 0.5086 (2) | 0.65173 (19) | 0.0436 (5) | |
| H8A | 0.0138 | 0.5988 | 0.6798 | 0.052* | |
| H8B | −0.0068 | 0.4706 | 0.6302 | 0.052* | |
| C9 | 0.1277 (3) | 0.41269 (19) | 0.76915 (19) | 0.0399 (4) | |
| C10 | −0.0218 (3) | 0.3515 (2) | 0.88308 (19) | 0.0403 (4) | |
| C11 | 0.0216 (3) | 0.2738 (2) | 1.0097 (2) | 0.0443 (5) | |
| C12 | −0.4696 (3) | 0.3219 (3) | 0.9528 (3) | 0.0694 (7) | |
| H12A | −0.5552 | 0.2765 | 1.0303 | 0.104* | |
| H12B | −0.4454 | 0.2809 | 0.8734 | 0.104* | |
| H12C | −0.5204 | 0.4195 | 0.9369 | 0.104* | |
| C13 | 0.1207 (5) | 0.0538 (3) | 1.1217 (3) | 0.0890 (9) | |
| H13A | 0.1554 | −0.0424 | 1.1090 | 0.134* | |
| H13B | 0.0174 | 0.0646 | 1.2040 | 0.134* | |
| H13C | 0.2215 | 0.0828 | 1.1287 | 0.134* | |
| N1 | 0.2241 (2) | 0.27441 (17) | 0.50850 (16) | 0.0448 (4) | |
| N2 | −0.1769 (2) | 0.36936 (18) | 0.86710 (16) | 0.0451 (4) | |
| O1 | 0.28034 (19) | 0.38332 (16) | 0.77643 (15) | 0.0530 (4) | |
| O2 | 0.0143 (3) | 0.32938 (19) | 1.09837 (17) | 0.0774 (5) | |
| O3 | 0.0721 (2) | 0.13890 (16) | 1.00578 (16) | 0.0638 (4) | |
| O4 | −0.30078 (19) | 0.30477 (17) | 0.97942 (15) | 0.0568 (4) | |
| S1 | 0.52463 (7) | 0.32799 (6) | 0.31355 (5) | 0.05263 (18) | |
| S2 | 0.27235 (7) | 0.53273 (5) | 0.50010 (5) | 0.04578 (17) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0938 (19) | 0.0544 (14) | 0.0641 (14) | −0.0322 (13) | −0.0349 (13) | 0.0011 (11) |
| C2 | 0.138 (3) | 0.0375 (13) | 0.093 (2) | −0.0260 (15) | −0.074 (2) | 0.0004 (13) |
| C3 | 0.103 (2) | 0.0500 (14) | 0.0869 (19) | 0.0087 (14) | −0.0594 (18) | −0.0267 (13) |
| C4 | 0.0734 (16) | 0.0570 (14) | 0.0702 (15) | 0.0041 (12) | −0.0340 (13) | −0.0302 (12) |
| C5 | 0.0562 (12) | 0.0444 (11) | 0.0480 (11) | −0.0042 (9) | −0.0252 (10) | −0.0131 (9) |
| C6 | 0.0596 (12) | 0.0385 (11) | 0.0474 (11) | −0.0108 (9) | −0.0292 (10) | −0.0048 (8) |
| C7 | 0.0414 (10) | 0.0418 (10) | 0.0358 (9) | −0.0071 (8) | −0.0154 (8) | −0.0082 (8) |
| C8 | 0.0432 (11) | 0.0490 (11) | 0.0406 (10) | 0.0008 (9) | −0.0174 (8) | −0.0155 (8) |
| C9 | 0.0420 (11) | 0.0403 (10) | 0.0438 (10) | 0.0002 (8) | −0.0203 (8) | −0.0174 (8) |
| C10 | 0.0438 (10) | 0.0413 (10) | 0.0424 (10) | −0.0005 (8) | −0.0213 (8) | −0.0155 (8) |
| C11 | 0.0440 (11) | 0.0488 (12) | 0.0439 (10) | −0.0041 (9) | −0.0188 (9) | −0.0127 (9) |
| C12 | 0.0513 (13) | 0.0842 (18) | 0.0843 (17) | −0.0193 (12) | −0.0342 (13) | −0.0082 (14) |
| C13 | 0.127 (3) | 0.0679 (18) | 0.0844 (19) | −0.0117 (17) | −0.068 (2) | 0.0130 (15) |
| N1 | 0.0484 (9) | 0.0457 (10) | 0.0433 (9) | −0.0136 (8) | −0.0150 (7) | −0.0077 (7) |
| N2 | 0.0446 (9) | 0.0497 (10) | 0.0449 (9) | −0.0089 (7) | −0.0185 (7) | −0.0088 (7) |
| O1 | 0.0438 (8) | 0.0620 (9) | 0.0594 (9) | −0.0054 (7) | −0.0272 (7) | −0.0094 (7) |
| O2 | 0.1180 (15) | 0.0696 (11) | 0.0605 (10) | 0.0034 (10) | −0.0516 (10) | −0.0270 (9) |
| O3 | 0.0931 (12) | 0.0467 (9) | 0.0642 (10) | −0.0046 (8) | −0.0473 (9) | −0.0069 (7) |
| O4 | 0.0463 (8) | 0.0745 (11) | 0.0546 (9) | −0.0184 (7) | −0.0238 (7) | 0.0000 (7) |
| S1 | 0.0523 (3) | 0.0552 (4) | 0.0485 (3) | −0.0167 (3) | −0.0037 (2) | −0.0193 (2) |
| S2 | 0.0515 (3) | 0.0413 (3) | 0.0472 (3) | −0.0109 (2) | −0.0144 (2) | −0.0131 (2) |
| C1—C6 | 1.389 (3) | C8—H8A | 0.9700 |
| C1—C2 | 1.397 (4) | C8—H8B | 0.9700 |
| C1—H1 | 0.9300 | C9—O1 | 1.210 (2) |
| C2—C3 | 1.387 (4) | C9—C10 | 1.493 (3) |
| C2—H2 | 0.9300 | C10—N2 | 1.279 (2) |
| C3—C4 | 1.362 (4) | C10—C11 | 1.506 (3) |
| C3—H3 | 0.9300 | C11—O2 | 1.182 (2) |
| C4—C5 | 1.398 (3) | C11—O3 | 1.315 (3) |
| C4—H4 | 0.9300 | C12—O4 | 1.445 (3) |
| C5—C6 | 1.398 (3) | C12—H12A | 0.9600 |
| C5—S1 | 1.736 (2) | C12—H12B | 0.9600 |
| C6—N1 | 1.397 (3) | C12—H12C | 0.9600 |
| C7—N1 | 1.291 (2) | C13—O3 | 1.450 (3) |
| C7—S2 | 1.745 (2) | C13—H13A | 0.9600 |
| C7—S1 | 1.753 (2) | C13—H13B | 0.9600 |
| C8—C9 | 1.507 (3) | C13—H13C | 0.9600 |
| C8—S2 | 1.800 (2) | N2—O4 | 1.386 (2) |
| C6—C1—C2 | 118.0 (3) | O1—C9—C10 | 118.71 (17) |
| C6—C1—H1 | 121.0 | O1—C9—C8 | 124.10 (19) |
| C2—C1—H1 | 121.0 | C10—C9—C8 | 117.19 (16) |
| C3—C2—C1 | 121.5 (2) | N2—C10—C9 | 118.18 (17) |
| C3—C2—H2 | 119.3 | N2—C10—C11 | 124.72 (18) |
| C1—C2—H2 | 119.3 | C9—C10—C11 | 117.11 (16) |
| C4—C3—C2 | 121.3 (2) | O2—C11—O3 | 125.40 (19) |
| C4—C3—H3 | 119.3 | O2—C11—C10 | 123.41 (19) |
| C2—C3—H3 | 119.3 | O3—C11—C10 | 111.17 (16) |
| C3—C4—C5 | 117.6 (3) | O4—C12—H12A | 109.5 |
| C3—C4—H4 | 121.2 | O4—C12—H12B | 109.5 |
| C5—C4—H4 | 121.2 | H12A—C12—H12B | 109.5 |
| C6—C5—C4 | 122.2 (2) | O4—C12—H12C | 109.5 |
| C6—C5—S1 | 109.43 (15) | H12A—C12—H12C | 109.5 |
| C4—C5—S1 | 128.4 (2) | H12B—C12—H12C | 109.5 |
| C1—C6—N1 | 124.8 (2) | O3—C13—H13A | 109.5 |
| C1—C6—C5 | 119.4 (2) | O3—C13—H13B | 109.5 |
| N1—C6—C5 | 115.76 (18) | H13A—C13—H13B | 109.5 |
| N1—C7—S2 | 124.48 (15) | O3—C13—H13C | 109.5 |
| N1—C7—S1 | 117.24 (15) | H13A—C13—H13C | 109.5 |
| S2—C7—S1 | 118.25 (11) | H13B—C13—H13C | 109.5 |
| C9—C8—S2 | 113.07 (14) | C7—N1—C6 | 109.26 (17) |
| C9—C8—H8A | 109.0 | C10—N2—O4 | 111.87 (15) |
| S2—C8—H8A | 109.0 | C11—O3—C13 | 115.94 (19) |
| C9—C8—H8B | 109.0 | N2—O4—C12 | 109.46 (16) |
| S2—C8—H8B | 109.0 | C5—S1—C7 | 88.31 (10) |
| H8A—C8—H8B | 107.8 | C7—S2—C8 | 98.95 (10) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O1i | 0.93 | 2.55 | 3.398 (3) | 152 |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O1i | 0.93 | 2.55 | 3.398 (3) | 152 |
| Symmetry codes: (i) −x+1, −y, −z+1. |
The authors acknowledge the National Key Technologies R&D Program of China (2006BAE01A01–13) for supporting this work.
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A wide range of biological activities have been attributed to compounds containing benzothiazole moiety such as anticancer (Bradshaw et al., 2008), antibacterial (Moharram et al., 1990) and cytotoxic activity (Spillane et al., 2007), Herein we present the crystal structure of the title benzothiazole derivative (I).
The crystal structure of the title compound (I) is represented in Fig. 1. There is a dihedral angle of 0.41 (13)° between the benzene ring and thiazole ring. In the crystal structure, weak intermolecular C—H···O interactions (Table 1), together with π-π stacking between parallel benzene rings of adjacent molecules stabilize the packing, the centroid-to-centroid distance of two benzene rings is 3.673 (2)Å (symmetry codes: 1 - x,-y,1 - z).