organic compounds
5-Chloro-2-(3,4,5-trimethoxyphenyl)-1,3-benzothiazole
aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
In the title compound, C16H14ClNO3S, the dihedral angle between the almost-planar benzothiazole ring system [maximum deviation = 0.012 (3) Å] and the aromatic ring of the trimethoxyphenyl group is 15.56 (6)°. In the crystal, the molecules are arranged into layers parallel to the bc plane, held together only by weak van der Waals forces.
Related literature
For the biological activites of benzothiazole compounds, see: Chohan et al. (2003); Hutchinson et al. (2002); Chua et al. (1999); Burger & Sawhney (1968); Palmer et al. (1971). For the crystal structures of related benzothiazole derivatives, see: Yousuf et al. (2012a,b).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812039372/rz5005sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039372/rz5005Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039372/rz5005Isup3.cml
A mixture of 2-amino-4-cholorobenzenethiol (0.159 g, 1 mmol), 3,4,5-trimethoxybenz-aldehyde (0.196 g, 1 mmol), sodium metabisulfite (0.2 g) and N,N-dimethylformamide (10 ml) was refluxed for 2 h in a round-bottomed flask. The completion of reaction was monitored by TLC. After cooling the mixture to room temperature, cold water was added to obtain a white precipitate. Crystallization from ethanol afforded crystals of the title compound (0.298 g, 88.9% yield) found suitable for X-ray diffraction studies.
H atoms were positioned geometrically with C—H = 0.96 or 0.93 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. A rotating group model was applied to methyl groups.
Benzothiazole is a well known class of sulfur- and nitrogen-containing heterocyclic aromatic molecules with a broad range of biological activities, such as antimicrobial, antitumoral, antimalarial and antitubercular (Chohan et al., 2003; Hutchinson et al., 2002; Chua et al., 1999; Burger & Sawhney, 1968; Palmer et al., 1971). The title compound is a benzothiazole derivative synthesized as a part of our ongoing project on bioactive hetereocyclic compounds.
The molecular structure of the title compound (Fig. 1) is similar to that reported for the recently published compounds 5-chloro-2-phenyl-1,3-benzothiazole (Yousuf et al., 2012a) and 2-(5-chloro-1,3-benzothiazol-2-yl)-4-methoxyphenol (Yousuf et al., 2012b) with the difference that the phenyl or p-methoxyphenol group is replaced by a trimethoxyphenyl group. The dihedral angle between the almost planar benzothiazole ring system (S1/N1/C1–C7) and the benzene ring of the trimethoxyphenyl group (C8–C13) is 15.56 (6)°. Bond lengths and angles are unexceptional. In the
the molecules are arranged into layers parallel to the bc plane (Fig. 2) held together only by weak van der Waals forces.For the biological activites of benzothiazole compounds, see: Chohan et al. (2003); Hutchinson et al. (2002); Chua et al. (1999); Burger & Sawhney (1968); Palmer et al. (1971). For the crystal structures of related benzothiazole derivatives, see: Yousuf et al. (2012a,b).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).C16H14ClNO3S | Z = 1 |
Mr = 335.79 | F(000) = 174 |
Triclinic, P1 | Dx = 1.460 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.0656 (6) Å | Cell parameters from 2110 reflections |
b = 7.7855 (11) Å | θ = 1.7–25.5° |
c = 12.2420 (17) Å | µ = 0.40 mm−1 |
α = 96.263 (3)° | T = 273 K |
β = 91.380 (3)° | Plate, colourless |
γ = 97.228 (3)° | 0.52 × 0.15 × 0.09 mm |
V = 381.84 (9) Å3 |
Bruker SMART APEX CCD diffractometer | 2816 independent reflections |
Radiation source: fine-focus sealed tube | 2621 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −4→4 |
Tmin = 0.820, Tmax = 0.965 | k = −9→9 |
4277 measured reflections | l = −14→14 |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0384P)2 + 0.0343P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2816 reflections | Δρmax = 0.14 e Å−3 |
202 parameters | Δρmin = −0.16 e Å−3 |
3 restraints | Absolute structure: Flack (1983), with 1402 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (6) |
C16H14ClNO3S | γ = 97.228 (3)° |
Mr = 335.79 | V = 381.84 (9) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.0656 (6) Å | Mo Kα radiation |
b = 7.7855 (11) Å | µ = 0.40 mm−1 |
c = 12.2420 (17) Å | T = 273 K |
α = 96.263 (3)° | 0.52 × 0.15 × 0.09 mm |
β = 91.380 (3)° |
Bruker SMART APEX CCD diffractometer | 2816 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2621 reflections with I > 2σ(I) |
Tmin = 0.820, Tmax = 0.965 | Rint = 0.014 |
4277 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.080 | Δρmax = 0.14 e Å−3 |
S = 1.07 | Δρmin = −0.16 e Å−3 |
2816 reflections | Absolute structure: Flack (1983), with 1402 Friedel pairs |
202 parameters | Absolute structure parameter: 0.12 (6) |
3 restraints |
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 | ||
S1 | 0.46803 (14) | 0.91830 (7) | 0.20220 (5) | 0.05768 (18) | |
Cl1 | 0.9092 (2) | 0.29518 (10) | 0.41340 (7) | 0.0924 (3) | |
O1 | −0.0441 (5) | 1.1670 (2) | −0.14201 (16) | 0.0662 (5) | |
O2 | 0.0285 (5) | 0.9542 (3) | −0.32262 (15) | 0.0703 (6) | |
O3 | 0.2731 (5) | 0.6534 (2) | −0.31396 (14) | 0.0670 (5) | |
N1 | 0.4815 (5) | 0.6095 (3) | 0.10078 (16) | 0.0510 (5) | |
C1 | 0.5921 (6) | 0.6053 (3) | 0.2087 (2) | 0.0483 (6) | |
C2 | 0.6876 (8) | 0.4599 (4) | 0.2507 (2) | 0.0603 (7) | |
H2A | 0.6804 | 0.3539 | 0.2070 | 0.072* | |
C3 | 0.7927 (7) | 0.4782 (4) | 0.3588 (2) | 0.0616 (7) | |
C4 | 0.8097 (7) | 0.6314 (4) | 0.4269 (2) | 0.0651 (8) | |
H4A | 0.8842 | 0.6378 | 0.4999 | 0.078* | |
C5 | 0.7142 (8) | 0.7758 (4) | 0.3852 (2) | 0.0651 (8) | |
H5A | 0.7238 | 0.8813 | 0.4296 | 0.078* | |
C6 | 0.6036 (6) | 0.7615 (3) | 0.2761 (2) | 0.0499 (6) | |
C7 | 0.4065 (5) | 0.7623 (3) | 0.08620 (18) | 0.0443 (5) | |
C8 | 0.2955 (5) | 0.8118 (3) | −0.01945 (19) | 0.0436 (5) | |
C9 | 0.1638 (6) | 0.9681 (3) | −0.0251 (2) | 0.0479 (5) | |
H9A | 0.1328 | 1.0395 | 0.0388 | 0.057* | |
C10 | 0.0797 (6) | 1.0154 (3) | −0.1272 (2) | 0.0495 (6) | |
C11 | 0.1223 (6) | 0.9078 (3) | −0.2224 (2) | 0.0523 (6) | |
C12 | 0.2466 (6) | 0.7500 (3) | −0.21641 (19) | 0.0498 (6) | |
C13 | 0.3346 (6) | 0.7029 (3) | −0.11455 (19) | 0.0496 (5) | |
H13A | 0.4198 | 0.5984 | −0.1100 | 0.060* | |
C14 | −0.1064 (8) | 1.2779 (4) | −0.0479 (3) | 0.0675 (7) | |
H14A | −0.2101 | 1.3735 | −0.0699 | 0.101* | |
H14B | 0.0992 | 1.3218 | −0.0085 | 0.101* | |
H14C | −0.2508 | 1.2140 | −0.0014 | 0.101* | |
C15 | 0.2896 (9) | 1.0281 (4) | −0.3824 (2) | 0.0788 (9) | |
H15A | 0.2008 | 1.0805 | −0.4421 | 0.118* | |
H15B | 0.4177 | 0.9390 | −0.4109 | 0.118* | |
H15C | 0.4291 | 1.1154 | −0.3349 | 0.118* | |
C16 | 0.4033 (8) | 0.4926 (4) | −0.3130 (2) | 0.0722 (8) | |
H16A | 0.4046 | 0.4368 | −0.3869 | 0.108* | |
H16B | 0.2677 | 0.4185 | −0.2695 | 0.108* | |
H16C | 0.6258 | 0.5138 | −0.2820 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0794 (4) | 0.0528 (4) | 0.0413 (3) | 0.0137 (3) | −0.0038 (3) | 0.0030 (3) |
Cl1 | 0.1234 (7) | 0.0817 (5) | 0.0763 (6) | 0.0143 (5) | −0.0310 (5) | 0.0349 (4) |
O1 | 0.0760 (13) | 0.0611 (11) | 0.0673 (12) | 0.0246 (10) | −0.0039 (9) | 0.0170 (9) |
O2 | 0.0682 (13) | 0.0986 (15) | 0.0487 (11) | 0.0164 (11) | −0.0162 (9) | 0.0271 (10) |
O3 | 0.0937 (14) | 0.0661 (12) | 0.0416 (10) | 0.0188 (10) | −0.0110 (9) | 0.0008 (8) |
N1 | 0.0684 (13) | 0.0473 (11) | 0.0368 (10) | 0.0066 (9) | −0.0086 (9) | 0.0065 (8) |
C1 | 0.0522 (14) | 0.0512 (14) | 0.0404 (14) | −0.0003 (11) | −0.0047 (10) | 0.0100 (11) |
C2 | 0.0778 (18) | 0.0532 (15) | 0.0498 (15) | 0.0072 (13) | −0.0096 (13) | 0.0102 (12) |
C3 | 0.0693 (18) | 0.0652 (18) | 0.0525 (17) | 0.0033 (14) | −0.0078 (13) | 0.0252 (14) |
C4 | 0.0791 (19) | 0.079 (2) | 0.0365 (14) | 0.0035 (16) | −0.0100 (13) | 0.0120 (13) |
C5 | 0.091 (2) | 0.0690 (18) | 0.0334 (13) | 0.0088 (16) | −0.0050 (13) | −0.0003 (12) |
C6 | 0.0539 (14) | 0.0541 (15) | 0.0407 (13) | 0.0045 (11) | −0.0001 (11) | 0.0041 (11) |
C7 | 0.0453 (13) | 0.0460 (13) | 0.0406 (13) | 0.0009 (10) | 0.0003 (10) | 0.0056 (10) |
C8 | 0.0436 (13) | 0.0464 (13) | 0.0405 (12) | 0.0005 (10) | −0.0017 (9) | 0.0106 (10) |
C9 | 0.0500 (13) | 0.0459 (13) | 0.0467 (13) | 0.0018 (10) | −0.0002 (10) | 0.0058 (10) |
C10 | 0.0435 (13) | 0.0495 (13) | 0.0579 (15) | 0.0050 (10) | −0.0029 (11) | 0.0189 (11) |
C11 | 0.0505 (13) | 0.0602 (15) | 0.0467 (14) | 0.0046 (11) | −0.0084 (10) | 0.0139 (11) |
C12 | 0.0533 (14) | 0.0553 (14) | 0.0403 (13) | 0.0045 (11) | −0.0052 (10) | 0.0076 (10) |
C13 | 0.0573 (14) | 0.0473 (13) | 0.0446 (13) | 0.0069 (11) | −0.0048 (10) | 0.0084 (10) |
C14 | 0.0626 (16) | 0.0536 (15) | 0.088 (2) | 0.0140 (12) | 0.0002 (14) | 0.0110 (13) |
C15 | 0.099 (2) | 0.087 (2) | 0.0558 (17) | 0.0127 (18) | −0.0040 (16) | 0.0311 (15) |
C16 | 0.093 (2) | 0.0726 (19) | 0.0516 (16) | 0.0205 (16) | −0.0017 (15) | −0.0021 (14) |
S1—C6 | 1.731 (3) | C5—H5A | 0.9300 |
S1—C7 | 1.756 (2) | C7—C8 | 1.466 (3) |
Cl1—C3 | 1.750 (3) | C8—C13 | 1.388 (3) |
O1—C10 | 1.368 (3) | C8—C9 | 1.397 (3) |
O1—C14 | 1.410 (4) | C9—C10 | 1.388 (3) |
O2—C11 | 1.375 (3) | C9—H9A | 0.9300 |
O2—C15 | 1.403 (3) | C10—C11 | 1.387 (4) |
O3—C12 | 1.354 (3) | C11—C12 | 1.395 (3) |
O3—C16 | 1.420 (3) | C12—C13 | 1.389 (3) |
N1—C7 | 1.294 (3) | C13—H13A | 0.9300 |
N1—C1 | 1.391 (3) | C14—H14A | 0.9600 |
C1—C2 | 1.387 (4) | C14—H14B | 0.9600 |
C1—C6 | 1.388 (3) | C14—H14C | 0.9600 |
C2—C3 | 1.368 (4) | C15—H15A | 0.9600 |
C2—H2A | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.372 (4) | C15—H15C | 0.9600 |
C4—C5 | 1.378 (4) | C16—H16A | 0.9600 |
C4—H4A | 0.9300 | C16—H16B | 0.9600 |
C5—C6 | 1.387 (4) | C16—H16C | 0.9600 |
C6—S1—C7 | 88.87 (11) | C8—C9—H9A | 120.4 |
C10—O1—C14 | 118.2 (2) | O1—C10—C11 | 115.7 (2) |
C11—O2—C15 | 114.8 (2) | O1—C10—C9 | 124.0 (2) |
C12—O3—C16 | 118.1 (2) | C11—C10—C9 | 120.4 (2) |
C7—N1—C1 | 110.9 (2) | O2—C11—C10 | 119.6 (2) |
C2—C1—C6 | 120.0 (2) | O2—C11—C12 | 120.0 (2) |
C2—C1—N1 | 124.9 (2) | C10—C11—C12 | 120.3 (2) |
C6—C1—N1 | 115.1 (2) | O3—C12—C13 | 124.8 (2) |
C3—C2—C1 | 117.5 (3) | O3—C12—C11 | 115.6 (2) |
C3—C2—H2A | 121.2 | C13—C12—C11 | 119.5 (2) |
C1—C2—H2A | 121.2 | C8—C13—C12 | 120.0 (2) |
C2—C3—C4 | 123.7 (3) | C8—C13—H13A | 120.0 |
C2—C3—Cl1 | 118.0 (2) | C12—C13—H13A | 120.0 |
C4—C3—Cl1 | 118.3 (2) | O1—C14—H14A | 109.5 |
C3—C4—C5 | 118.8 (3) | O1—C14—H14B | 109.5 |
C3—C4—H4A | 120.6 | H14A—C14—H14B | 109.5 |
C5—C4—H4A | 120.6 | O1—C14—H14C | 109.5 |
C4—C5—C6 | 119.1 (3) | H14A—C14—H14C | 109.5 |
C4—C5—H5A | 120.5 | H14B—C14—H14C | 109.5 |
C6—C5—H5A | 120.5 | O2—C15—H15A | 109.5 |
C5—C6—C1 | 120.9 (2) | O2—C15—H15B | 109.5 |
C5—C6—S1 | 129.3 (2) | H15A—C15—H15B | 109.5 |
C1—C6—S1 | 109.74 (19) | O2—C15—H15C | 109.5 |
N1—C7—C8 | 124.4 (2) | H15A—C15—H15C | 109.5 |
N1—C7—S1 | 115.40 (17) | H15B—C15—H15C | 109.5 |
C8—C7—S1 | 120.09 (17) | O3—C16—H16A | 109.5 |
C13—C8—C9 | 120.5 (2) | O3—C16—H16B | 109.5 |
C13—C8—C7 | 118.58 (19) | H16A—C16—H16B | 109.5 |
C9—C8—C7 | 120.9 (2) | O3—C16—H16C | 109.5 |
C10—C9—C8 | 119.2 (2) | H16A—C16—H16C | 109.5 |
C10—C9—H9A | 120.4 | H16B—C16—H16C | 109.5 |
C7—N1—C1—C2 | 179.2 (2) | S1—C7—C8—C9 | −15.0 (3) |
C7—N1—C1—C6 | −0.9 (3) | C13—C8—C9—C10 | −1.5 (3) |
C6—C1—C2—C3 | −0.4 (4) | C7—C8—C9—C10 | 176.2 (2) |
N1—C1—C2—C3 | 179.5 (3) | C14—O1—C10—C11 | 177.3 (2) |
C1—C2—C3—C4 | −0.3 (4) | C14—O1—C10—C9 | −3.4 (3) |
C1—C2—C3—Cl1 | 179.2 (2) | C8—C9—C10—O1 | −178.5 (2) |
C2—C3—C4—C5 | 0.4 (5) | C8—C9—C10—C11 | 0.7 (3) |
Cl1—C3—C4—C5 | −179.1 (2) | C15—O2—C11—C10 | 100.9 (3) |
C3—C4—C5—C6 | 0.1 (5) | C15—O2—C11—C12 | −81.8 (3) |
C4—C5—C6—C1 | −0.8 (4) | O1—C10—C11—O2 | −2.6 (3) |
C4—C5—C6—S1 | 179.7 (2) | C9—C10—C11—O2 | 178.1 (2) |
C2—C1—C6—C5 | 0.9 (4) | O1—C10—C11—C12 | −179.9 (2) |
N1—C1—C6—C5 | −179.0 (2) | C9—C10—C11—C12 | 0.7 (3) |
C2—C1—C6—S1 | −179.5 (2) | C16—O3—C12—C13 | −0.7 (4) |
N1—C1—C6—S1 | 0.6 (3) | C16—O3—C12—C11 | 179.0 (2) |
C7—S1—C6—C5 | 179.4 (3) | O2—C11—C12—O3 | 1.6 (3) |
C7—S1—C6—C1 | −0.09 (18) | C10—C11—C12—O3 | 178.9 (2) |
C1—N1—C7—C8 | 177.3 (2) | O2—C11—C12—C13 | −178.8 (2) |
C1—N1—C7—S1 | 0.8 (3) | C10—C11—C12—C13 | −1.5 (3) |
C6—S1—C7—N1 | −0.43 (19) | C9—C8—C13—C12 | 0.8 (3) |
C6—S1—C7—C8 | −177.11 (19) | C7—C8—C13—C12 | −177.0 (2) |
N1—C7—C8—C13 | −13.6 (3) | O3—C12—C13—C8 | −179.7 (2) |
S1—C7—C8—C13 | 162.74 (17) | C11—C12—C13—C8 | 0.7 (3) |
N1—C7—C8—C9 | 168.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C16H14ClNO3S |
Mr | 335.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 4.0656 (6), 7.7855 (11), 12.2420 (17) |
α, β, γ (°) | 96.263 (3), 91.380 (3), 97.228 (3) |
V (Å3) | 381.84 (9) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.52 × 0.15 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.820, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4277, 2816, 2621 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.080, 1.07 |
No. of reflections | 2816 |
No. of parameters | 202 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Absolute structure | Flack (1983), with 1402 Friedel pairs |
Absolute structure parameter | 0.12 (6) |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Acknowledgements
The authors are grateful to OPCW, The Netherlands, and the Higher Education Commission (HEC), Pakistan (project No. 1910), for their financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzothiazole is a well known class of sulfur- and nitrogen-containing heterocyclic aromatic molecules with a broad range of biological activities, such as antimicrobial, antitumoral, antimalarial and antitubercular (Chohan et al., 2003; Hutchinson et al., 2002; Chua et al., 1999; Burger & Sawhney, 1968; Palmer et al., 1971). The title compound is a benzothiazole derivative synthesized as a part of our ongoing project on bioactive hetereocyclic compounds.
The molecular structure of the title compound (Fig. 1) is similar to that reported for the recently published compounds 5-chloro-2-phenyl-1,3-benzothiazole (Yousuf et al., 2012a) and 2-(5-chloro-1,3-benzothiazol-2-yl)-4-methoxyphenol (Yousuf et al., 2012b) with the difference that the phenyl or p-methoxyphenol group is replaced by a trimethoxyphenyl group. The dihedral angle between the almost planar benzothiazole ring system (S1/N1/C1–C7) and the benzene ring of the trimethoxyphenyl group (C8–C13) is 15.56 (6)°. Bond lengths and angles are unexceptional. In the crystal structure the molecules are arranged into layers parallel to the bc plane (Fig. 2) held together only by weak van der Waals forces.