organic compounds
(2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone
aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, bCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy, and cSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
*Correspondence e-mail: venugopala@ukzn.ac.za, nksusa@gmail.com
In the title compound, C21H14ClNO2S, the dihedral angle between the benzothiazole and diphenyl methanone groups is 68.6 (2)°. The consists of dimeric units generated by C—H⋯N bonds, further linked by C—H⋯O bonds and C—H⋯π and π–π interactions [centroid–centroiddistance = 3.856 (2) Å], which lead to a criss-cross assembly parallel to (001).
Related literature
For background to the applications of benzothiazole derivatives, see: Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: COLLECT (Nonius, 1998); cell DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Supporting information
10.1107/S1600536812041888/bg2479sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041888/bg2479Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812041888/bg2479Isup3.cml
To a solution of 2-(chloromethyl)-benzo-thiazole (0.5 g, 0.0027 mol) and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.0027 mol) in dry THF, dry potassium carbonate (0.38 g, 0.0027 mol) was added and stirred at room temperature. The reaction mixture was concentrated to remove the solvent, diluted with ethyl acetate, washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated to yield a residue which was purified by
using ethyl acetate and n-hexane as (7:3, Rf = 0.68) to afford as a white solid product (Yield 70.8%; m. p. 403 (2) K).Suitable crystals for single-crystal X-ray study were obtained by slow evaporation crystallization from ethanol solvent at room temperature.All H atoms were positioned geometrically and refined using a riding model with Uiso(H)= 1.2 Ueq(C). The
might be considered as Pbca only on average, since there are many violations of the a glide condition. This may be the reason for some Fo-Fc discrepancies. in lower symmetry groups, however, did not improve the results.Data collection: COLLECT (Nonius, 1998); cell
DENZO-SMN (Otwinowski & Minor,1997); data reduction: DENZO-SMN (Otwinowski & Minor,1997); 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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).C21H14ClNO2S | Dx = 1.435 Mg m−3 |
Mr = 379.84 | Melting point: 403(2) K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 560 reflections |
a = 7.4598 (3) Å | θ = 1.7–25.3° |
b = 19.3131 (8) Å | µ = 0.35 mm−1 |
c = 24.4002 (9) Å | T = 173 K |
V = 3515.4 (2) Å3 | Plate, colourless |
Z = 8 | 0.22 × 0.16 × 0.03 mm |
F(000) = 1568 |
Nonius KappaCCD diffractometer | 3206 independent reflections |
Radiation source: fine-focus sealed tube | 2576 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
1.2° ϕ scans and ω scans | θmax = 25.3°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −8→8 |
Tmin = 0.927, Tmax = 0.990 | k = −23→23 |
52834 measured reflections | l = −29→29 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.30 | w = 1/[σ2(Fo2) + (0.071P)2 + 8.1626P] where P = (Fo2 + 2Fc2)/3 |
3206 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C21H14ClNO2S | V = 3515.4 (2) Å3 |
Mr = 379.84 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.4598 (3) Å | µ = 0.35 mm−1 |
b = 19.3131 (8) Å | T = 173 K |
c = 24.4002 (9) Å | 0.22 × 0.16 × 0.03 mm |
Nonius KappaCCD diffractometer | 3206 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | 2576 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.990 | Rint = 0.063 |
52834 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.30 | Δρmax = 0.66 e Å−3 |
3206 reflections | Δρmin = −0.33 e Å−3 |
235 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.34601 (15) | 0.06802 (6) | 0.39552 (4) | 0.0309 (3) | |
Cl1 | 0.68528 (18) | 0.27003 (7) | 0.68940 (5) | 0.0470 (4) | |
O1 | 0.4110 (4) | 0.11200 (15) | 0.50149 (11) | 0.0315 (7) | |
N1 | 0.1614 (5) | −0.02826 (17) | 0.44408 (14) | 0.0273 (8) | |
C6 | 0.1481 (5) | −0.0405 (2) | 0.38812 (17) | 0.0270 (9) | |
C7 | 0.2577 (5) | 0.0259 (2) | 0.45299 (16) | 0.0256 (9) | |
C8 | 0.2953 (6) | 0.0542 (2) | 0.50881 (16) | 0.0276 (9) | |
H8A | 0.1825 | 0.0688 | 0.5268 | 0.033* | |
H8B | 0.3537 | 0.0187 | 0.5319 | 0.033* | |
O2 | 0.5685 (4) | 0.29934 (15) | 0.47346 (12) | 0.0373 (8) | |
C14 | 0.5686 (5) | 0.2081 (2) | 0.53676 (16) | 0.0245 (9) | |
C15 | 0.5962 (5) | 0.2376 (2) | 0.48050 (17) | 0.0258 (9) | |
C16 | 0.6632 (5) | 0.1936 (2) | 0.43523 (16) | 0.0240 (9) | |
C17 | 0.7650 (5) | 0.1344 (2) | 0.44537 (16) | 0.0266 (9) | |
H17 | 0.7872 | 0.1203 | 0.4820 | 0.032* | |
C13 | 0.6296 (5) | 0.2462 (2) | 0.58122 (17) | 0.0286 (9) | |
H13 | 0.6917 | 0.2885 | 0.5753 | 0.034* | |
C9 | 0.4719 (5) | 0.1466 (2) | 0.54683 (16) | 0.0252 (9) | |
C19 | 0.8018 (7) | 0.1161 (3) | 0.34894 (19) | 0.0400 (11) | |
H19 | 0.8501 | 0.0899 | 0.3195 | 0.048* | |
C10 | 0.4403 (6) | 0.1248 (2) | 0.60021 (17) | 0.0305 (9) | |
H10 | 0.3735 | 0.0837 | 0.6068 | 0.037* | |
C18 | 0.8338 (6) | 0.0963 (2) | 0.40225 (19) | 0.0340 (10) | |
H18 | 0.9036 | 0.0562 | 0.4095 | 0.041* | |
C11 | 0.5061 (6) | 0.1629 (2) | 0.64375 (17) | 0.0336 (10) | |
H11 | 0.4862 | 0.1477 | 0.6803 | 0.040* | |
C1 | 0.2398 (6) | 0.0070 (2) | 0.35491 (17) | 0.0286 (9) | |
C12 | 0.6004 (6) | 0.2229 (2) | 0.63404 (17) | 0.0301 (10) | |
C20 | 0.6980 (7) | 0.1747 (3) | 0.33833 (18) | 0.0409 (12) | |
H20 | 0.6730 | 0.1878 | 0.3016 | 0.049* | |
C5 | 0.0510 (6) | −0.0945 (2) | 0.36427 (19) | 0.0347 (10) | |
H5 | −0.0113 | −0.1271 | 0.3863 | 0.042* | |
C4 | 0.0477 (7) | −0.0993 (2) | 0.30759 (19) | 0.0407 (11) | |
H4 | −0.0177 | −0.1357 | 0.2907 | 0.049* | |
C21 | 0.6322 (6) | 0.2134 (2) | 0.38092 (18) | 0.0340 (10) | |
H21 | 0.5647 | 0.2540 | 0.3735 | 0.041* | |
C2 | 0.2347 (7) | 0.0017 (3) | 0.29783 (19) | 0.0400 (11) | |
H2 | 0.2961 | 0.0341 | 0.2754 | 0.048* | |
C3 | 0.1385 (7) | −0.0517 (3) | 0.2751 (2) | 0.0442 (12) | |
H3 | 0.1340 | −0.0562 | 0.2364 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0343 (6) | 0.0302 (6) | 0.0282 (6) | −0.0080 (5) | 0.0014 (4) | 0.0005 (4) |
Cl1 | 0.0576 (8) | 0.0537 (8) | 0.0296 (6) | −0.0104 (6) | −0.0051 (5) | −0.0114 (5) |
O1 | 0.0351 (17) | 0.0341 (16) | 0.0253 (14) | −0.0140 (14) | 0.0015 (12) | −0.0025 (12) |
N1 | 0.0278 (19) | 0.0235 (18) | 0.0308 (18) | 0.0005 (15) | −0.0023 (15) | 0.0018 (15) |
C6 | 0.023 (2) | 0.026 (2) | 0.032 (2) | 0.0039 (17) | −0.0003 (17) | −0.0032 (17) |
C7 | 0.021 (2) | 0.025 (2) | 0.031 (2) | 0.0018 (17) | 0.0013 (17) | 0.0008 (17) |
C8 | 0.028 (2) | 0.026 (2) | 0.029 (2) | −0.0050 (18) | 0.0022 (17) | 0.0020 (17) |
O2 | 0.051 (2) | 0.0240 (16) | 0.0366 (17) | 0.0032 (14) | 0.0062 (15) | 0.0024 (13) |
C14 | 0.023 (2) | 0.024 (2) | 0.027 (2) | 0.0019 (17) | 0.0009 (17) | −0.0010 (16) |
C15 | 0.022 (2) | 0.025 (2) | 0.030 (2) | −0.0031 (17) | −0.0016 (17) | 0.0019 (17) |
C16 | 0.023 (2) | 0.023 (2) | 0.026 (2) | −0.0022 (17) | 0.0002 (16) | 0.0027 (17) |
C17 | 0.024 (2) | 0.028 (2) | 0.027 (2) | −0.0004 (18) | −0.0004 (17) | 0.0006 (17) |
C13 | 0.026 (2) | 0.028 (2) | 0.032 (2) | −0.0024 (18) | 0.0015 (18) | −0.0033 (17) |
C9 | 0.023 (2) | 0.028 (2) | 0.025 (2) | 0.0003 (17) | −0.0020 (16) | −0.0040 (16) |
C19 | 0.044 (3) | 0.043 (3) | 0.033 (2) | −0.005 (2) | 0.011 (2) | −0.011 (2) |
C10 | 0.030 (2) | 0.031 (2) | 0.030 (2) | −0.0041 (19) | 0.0025 (18) | 0.0026 (18) |
C18 | 0.026 (2) | 0.032 (2) | 0.044 (3) | 0.0014 (18) | 0.0013 (19) | −0.007 (2) |
C11 | 0.036 (2) | 0.041 (3) | 0.024 (2) | 0.001 (2) | 0.0025 (18) | 0.0024 (19) |
C1 | 0.025 (2) | 0.031 (2) | 0.030 (2) | 0.0018 (18) | −0.0015 (18) | −0.0024 (18) |
C12 | 0.029 (2) | 0.035 (2) | 0.026 (2) | 0.0031 (19) | −0.0021 (17) | −0.0066 (18) |
C20 | 0.056 (3) | 0.044 (3) | 0.023 (2) | −0.005 (2) | 0.000 (2) | 0.004 (2) |
C5 | 0.033 (2) | 0.028 (2) | 0.043 (3) | −0.001 (2) | −0.002 (2) | −0.005 (2) |
C4 | 0.044 (3) | 0.038 (3) | 0.040 (3) | −0.004 (2) | −0.008 (2) | −0.014 (2) |
C21 | 0.043 (3) | 0.029 (2) | 0.030 (2) | −0.002 (2) | −0.004 (2) | 0.0076 (18) |
C2 | 0.046 (3) | 0.043 (3) | 0.030 (2) | −0.006 (2) | 0.003 (2) | −0.001 (2) |
C3 | 0.049 (3) | 0.053 (3) | 0.031 (2) | −0.004 (2) | −0.002 (2) | −0.008 (2) |
S1—C1 | 1.731 (4) | C13—H13 | 0.9500 |
S1—C7 | 1.750 (4) | C9—C10 | 1.389 (6) |
Cl1—C12 | 1.747 (4) | C19—C18 | 1.377 (7) |
O1—C9 | 1.370 (5) | C19—C20 | 1.396 (7) |
O1—C8 | 1.422 (5) | C19—H19 | 0.9500 |
N1—C7 | 1.288 (5) | C10—C11 | 1.383 (6) |
N1—C6 | 1.389 (5) | C10—H10 | 0.9500 |
C6—C5 | 1.397 (6) | C18—H18 | 0.9500 |
C6—C1 | 1.402 (6) | C11—C12 | 1.377 (6) |
C7—C8 | 1.494 (6) | C11—H11 | 0.9500 |
C8—H8A | 0.9900 | C1—C2 | 1.397 (6) |
C8—H8B | 0.9900 | C20—C21 | 1.371 (6) |
O2—C15 | 1.223 (5) | C20—H20 | 0.9500 |
C14—C13 | 1.388 (6) | C5—C4 | 1.386 (6) |
C14—C9 | 1.411 (6) | C5—H5 | 0.9500 |
C14—C15 | 1.500 (6) | C4—C3 | 1.390 (7) |
C15—C16 | 1.480 (6) | C4—H4 | 0.9500 |
C16—C17 | 1.394 (6) | C21—H21 | 0.9500 |
C16—C21 | 1.399 (6) | C2—C3 | 1.372 (7) |
C17—C18 | 1.383 (6) | C2—H2 | 0.9500 |
C17—H17 | 0.9500 | C3—H3 | 0.9500 |
C13—C12 | 1.382 (6) | ||
C1—S1—C7 | 88.3 (2) | C20—C19—H19 | 120.1 |
C9—O1—C8 | 118.8 (3) | C11—C10—C9 | 119.9 (4) |
C7—N1—C6 | 110.1 (3) | C11—C10—H10 | 120.0 |
N1—C6—C5 | 125.0 (4) | C9—C10—H10 | 120.0 |
N1—C6—C1 | 115.0 (4) | C19—C18—C17 | 120.5 (4) |
C5—C6—C1 | 120.0 (4) | C19—C18—H18 | 119.8 |
N1—C7—C8 | 123.8 (4) | C17—C18—H18 | 119.8 |
N1—C7—S1 | 116.9 (3) | C12—C11—C10 | 119.9 (4) |
C8—C7—S1 | 119.3 (3) | C12—C11—H11 | 120.1 |
O1—C8—C7 | 106.6 (3) | C10—C11—H11 | 120.1 |
O1—C8—H8A | 110.4 | C2—C1—C6 | 121.0 (4) |
C7—C8—H8A | 110.4 | C2—C1—S1 | 129.3 (4) |
O1—C8—H8B | 110.4 | C6—C1—S1 | 109.7 (3) |
C7—C8—H8B | 110.4 | C11—C12—C13 | 121.0 (4) |
H8A—C8—H8B | 108.6 | C11—C12—Cl1 | 119.4 (3) |
C13—C14—C9 | 118.6 (4) | C13—C12—Cl1 | 119.6 (3) |
C13—C14—C15 | 118.0 (4) | C21—C20—C19 | 120.0 (4) |
C9—C14—C15 | 123.3 (4) | C21—C20—H20 | 120.0 |
O2—C15—C16 | 120.8 (4) | C19—C20—H20 | 120.0 |
O2—C15—C14 | 118.4 (4) | C4—C5—C6 | 118.3 (4) |
C16—C15—C14 | 120.7 (3) | C4—C5—H5 | 120.8 |
C17—C16—C21 | 118.8 (4) | C6—C5—H5 | 120.8 |
C17—C16—C15 | 121.5 (4) | C5—C4—C3 | 121.1 (4) |
C21—C16—C15 | 119.6 (4) | C5—C4—H4 | 119.5 |
C18—C17—C16 | 120.2 (4) | C3—C4—H4 | 119.5 |
C18—C17—H17 | 119.9 | C20—C21—C16 | 120.7 (4) |
C16—C17—H17 | 119.9 | C20—C21—H21 | 119.7 |
C12—C13—C14 | 120.3 (4) | C16—C21—H21 | 119.7 |
C12—C13—H13 | 119.8 | C3—C2—C1 | 118.2 (4) |
C14—C13—H13 | 119.8 | C3—C2—H2 | 120.9 |
O1—C9—C10 | 123.6 (4) | C1—C2—H2 | 120.9 |
O1—C9—C14 | 116.1 (3) | C2—C3—C4 | 121.4 (4) |
C10—C9—C14 | 120.4 (4) | C2—C3—H3 | 119.3 |
C18—C19—C20 | 119.8 (4) | C4—C3—H3 | 119.3 |
C18—C19—H19 | 120.1 | ||
C7—N1—C6—C5 | −178.9 (4) | O1—C9—C10—C11 | −179.8 (4) |
C7—N1—C6—C1 | 0.2 (5) | C14—C9—C10—C11 | −1.0 (6) |
C6—N1—C7—C8 | 178.7 (4) | C20—C19—C18—C17 | −0.5 (7) |
C6—N1—C7—S1 | −0.7 (5) | C16—C17—C18—C19 | −0.4 (6) |
C1—S1—C7—N1 | 0.8 (3) | C9—C10—C11—C12 | 1.0 (7) |
C1—S1—C7—C8 | −178.6 (3) | N1—C6—C1—C2 | −178.7 (4) |
C9—O1—C8—C7 | −177.9 (3) | C5—C6—C1—C2 | 0.5 (7) |
N1—C7—C8—O1 | 177.7 (4) | N1—C6—C1—S1 | 0.4 (5) |
S1—C7—C8—O1 | −2.9 (5) | C5—C6—C1—S1 | 179.6 (3) |
C13—C14—C15—O2 | −42.2 (5) | C7—S1—C1—C2 | 178.3 (5) |
C9—C14—C15—O2 | 132.7 (4) | C7—S1—C1—C6 | −0.6 (3) |
C13—C14—C15—C16 | 135.0 (4) | C10—C11—C12—C13 | 0.5 (7) |
C9—C14—C15—C16 | −50.1 (6) | C10—C11—C12—Cl1 | −179.2 (3) |
O2—C15—C16—C17 | 152.4 (4) | C14—C13—C12—C11 | −2.0 (6) |
C14—C15—C16—C17 | −24.8 (6) | C14—C13—C12—Cl1 | 177.7 (3) |
O2—C15—C16—C21 | −24.3 (6) | C18—C19—C20—C21 | 1.6 (7) |
C14—C15—C16—C21 | 158.5 (4) | N1—C6—C5—C4 | 178.8 (4) |
C21—C16—C17—C18 | 0.1 (6) | C1—C6—C5—C4 | −0.3 (6) |
C15—C16—C17—C18 | −176.6 (4) | C6—C5—C4—C3 | 0.0 (7) |
C9—C14—C13—C12 | 2.0 (6) | C19—C20—C21—C16 | −1.9 (7) |
C15—C14—C13—C12 | 177.1 (4) | C17—C16—C21—C20 | 1.1 (7) |
C8—O1—C9—C10 | 6.1 (6) | C15—C16—C21—C20 | 177.8 (4) |
C8—O1—C9—C14 | −172.8 (3) | C6—C1—C2—C3 | −0.5 (7) |
C13—C14—C9—O1 | 178.4 (3) | S1—C1—C2—C3 | −179.3 (4) |
C15—C14—C9—O1 | 3.6 (6) | C1—C2—C3—C4 | 0.2 (8) |
C13—C14—C9—C10 | −0.5 (6) | C5—C4—C3—C2 | 0.0 (8) |
C15—C14—C9—C10 | −175.3 (4) |
Cg1 is the centroid of the S1/C1/C6/N1/C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···N1i | 0.95 | 2.56 | 3.432 (5) | 153 |
C5—H5···O2ii | 0.95 | 2.59 | 3.478 (5) | 155 |
C18—H18···Cg1iii | 0.95 | 2.62 | 3.433 (5) | 144 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y−1/2, z; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H14ClNO2S |
Mr | 379.84 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 173 |
a, b, c (Å) | 7.4598 (3), 19.3131 (8), 24.4002 (9) |
V (Å3) | 3515.4 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.22 × 0.16 × 0.03 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2008) |
Tmin, Tmax | 0.927, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 52834, 3206, 2576 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.200, 1.30 |
No. of reflections | 3206 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.33 |
Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor,1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Cg1 is the centroid of the S1/C1/C6/N1/C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···N1i | 0.9500 | 2.5600 | 3.432 (5) | 153 |
C5—H5···O2ii | 0.9500 | 2.5900 | 3.478 (5) | 155 |
C18—H18···Cg1iii | 0.9500 | 2.6200 | 3.433 (5) | 144 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y−1/2, z; (iii) x+1, y, z. |
Acknowledgements
The authors wish to thank the University of KwaZulu-Natal, South Africa, for facilities and Dr Hong Su, Department of Chemistry, University of Cape Town, for the data collection.
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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.
Our interest in the molecular design of the benzothiazole moiety is due to its diverse chemical and biological activities. Benzothiazole derivatives exhibit biological activities as antitumor, antiinflammatory, analgesic, antimicrobial, and potential anti HIV agents etc. Still the variety of biological features of new benzothiazole derivatives are of great scientific interest Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010). Here, we report the single-crystal structure of the title compound, C21H14ClNO2S.
The molecule adopts a conformation with a 68.6 (2)° dihedral angle between the planes of the benzothiazole and diphenyl methanone groups (Fig. 1). The weak C—H···N hydrogen bonds (Table 1, 1st entry) form dimeric units (Fig. 2a), in turn linked by the C—H···O ones (Table 1, 2nd entry) into planar arrays parallel to (001). This 2D structure is reinforced by a C-H···π bond involving the five-membered ring S1/C1/C6/N1/C7 (centroid Cg1) (Table 1, third entry) and a π···π bond between the C10—C14 six-membered ring (centroid Cg2) and the C16—C21 six-membered ring (centroid Cg3), viz., Cg2···Cg3i, (i): 1/2 + x, 1/2 - y, -z, with an intercentroid distance of 3.856 (2) Å, all these interactions leading to the criss-cross assembly depicted in Fig 2b.