organic compounds
6-Fluoro-2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, and cDepartment of Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my
The 16H11FN2OS, comprises two independent molecules in which the benzothiazole rings are essentially planar, with maximum deviations of 0.038 (2) and 0.045 (3) Å. The central benzothiazole ring makes dihedral angles of 4.87 (13) and 0.64 (12)° and 4.04 (12) and 3.67 (12)° with the two terminal phenyl rings in the two independent molecules. In the crystal, molecules are connected via weak intermolecular C—H⋯O hydrogen bonds forming supramolecular chains along the c axis.
of the title compound, CRelated literature
For details and applications of benzothiazoles, see: Yaseen et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Mittal et al. (2007); Bowyer et al. (2007); Pozas et al. (2005); Rana et al. (2008); Saha et al. (2000); Katritzky & Rees (1984). For bond-length data, see: Allen et al. (1987). For a related structure, see: Fun et al. (2011).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536811046666/bq2315sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046666/bq2315Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046666/bq2315Isup3.cml
A mixture of 5-fluorobenzothiazole amine (0.5 g, 2.99 mmol) and 2-bromo-1- (4-methoxyphenyl)ethanone (0.75 g, 3.29 mmol) in ethanol (10 ml) were irradiated with microwave at 130 °C for 45 min. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane (50 ml), washed with 10% sodium bicarbonate (2 X 50 ml), water (50 ml) and finally with saturated brine solution (2 X 50 ml). The organic layer was dried using anhydrous sodium sulphate and then evaporated under vacuum. The crude material was recrystallized by using dichloromethane and methanol to afford the title compound (0.7 g, 78 %) as colorless crystals. mp:450.9–451.9 K (Solvent of Crystallization: 1:1 dichloromethane : methanol).
All hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C). A rotating group model was applied to the methyl groups. 3649 Friedel pairs were used to determine the absolute configuration.
Benzothiazoles are very important bicyclic ring compounds which are of great interest because of their biological activities. The substituted benzothiazole derivatives have emerged as significant components in various diversified therapeutic applications. Literature review has shown that benzothiazoles and their derivatives show considerable properties, including potent inhibition of human immunodeficiency virus type 1 (HIV-1), replication by HIV-1 protease (Yaseen et al., 2006), antitumor (Kini et al., 2007), anthelmintic (Munirajasekhar et al., 2011) analgesic and anti-inflammatory (Gurupadayya et al., 2008), antimalarial (Bowyer et al., 2007), antifungal (Mittal et al., 2007), anticandidous (Pozas et al., 2005) and various CNS activities (Rana et al., 2008). Imidazole has become an important part of many pharmaceuticals. Synthetic imidazoles are present in many fungicides and antifungals (Saha et al., 2000), antiprotozoal and antihypertensive medications. Imidazole is part of the theophylline molecule, found in tea leaves and coffee beans, that stimulates the central nervous system. It is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities (Katritzky & Rees, 1984). The structure of a related compound 7-Chloro-3-phenylbenzo[4,5]thiazolo-[2,3-c][1,2,4] triazole has been reported by Fun et al., 2011.
In continuation of our research investigation, a new fused imidazo[2,1-b]thiazole derivative was prepared by the reaction of flurobenzothiazole amine with 4-methoxy phenacyl bromide under microwave irradiation at 130 °C and its
is reported here.The
of the title compound consists of two crystallographically independent molecules, (A & B), as shown in Fig. 1. The bond lengths and angles of molecules A and B agree with each other and are within normal ranges (Allen et al., 1987). The benzothiazole units are essentially planar with maximum deviations of 0.038 (2) Å for atom N1A (molecule A) and 0.045 (3) Å for atom C7B (molecule B). The dihedral angles that the central benzothiazole (S1/N1,N2/C1,C2,C7–C9) ring makes with the two terminal phenyl (C2–C7/C10–C15) rings in the two independent molecules are 4.87 (13)° : 0.64 (12)° for molecule A and 4.04 (12)° : 3.67 (12)° for molecule B.In the
(Fig. 2), the molecules are connected via weak intermolecular C—H···O hydrogen bonds forming one-dimensional supramolecular chains along the c-axis.For details and applications of benzothiazoles, see: Yaseen et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Mittal et al. (2007); Bowyer et al. (2007); Pozas et al. (2005); Rana et al. (2008); Saha et al. (2000); Katritzky & Rees (1984). For bond-length data, see: Allen et al. (1987). For a related structure, see: Fun et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C16H11FN2OS | F(000) = 616 |
Mr = 298.33 | Dx = 1.488 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3518 reflections |
a = 7.6120 (13) Å | θ = 2.2–23.5° |
b = 13.883 (2) Å | µ = 0.25 mm−1 |
c = 13.049 (2) Å | T = 296 K |
β = 105.117 (3)° | Block, colourless |
V = 1331.3 (4) Å3 | 0.31 × 0.30 × 0.13 mm |
Z = 4 |
Bruker APEXII DUO CCD area-detector diffractometer | 7656 independent reflections |
Radiation source: fine-focus sealed tube | 4268 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 30.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −8→10 |
Tmin = 0.926, Tmax = 0.967 | k = −19→19 |
20506 measured reflections | l = −18→18 |
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)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0433P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
7656 reflections | Δρmax = 0.24 e Å−3 |
381 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 3649 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (8) |
C16H11FN2OS | V = 1331.3 (4) Å3 |
Mr = 298.33 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.6120 (13) Å | µ = 0.25 mm−1 |
b = 13.883 (2) Å | T = 296 K |
c = 13.049 (2) Å | 0.31 × 0.30 × 0.13 mm |
β = 105.117 (3)° |
Bruker APEXII DUO CCD area-detector diffractometer | 7656 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4268 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 0.967 | Rint = 0.051 |
20506 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.116 | Δρmax = 0.24 e Å−3 |
S = 1.00 | Δρmin = −0.25 e Å−3 |
7656 reflections | Absolute structure: Flack (1983), 3649 Friedel pairs |
381 parameters | Absolute structure parameter: 0.00 (8) |
1 restraint |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
S1A | 0.85944 (11) | 1.02159 (6) | 0.83180 (6) | 0.0574 (2) | |
F1A | 1.5287 (3) | 0.92386 (17) | 0.98451 (18) | 0.0787 (7) | |
O1A | 0.1100 (4) | 0.95521 (17) | 0.15032 (18) | 0.0642 (7) | |
N1A | 0.9233 (4) | 0.96545 (17) | 0.65606 (19) | 0.0406 (6) | |
N2A | 0.6279 (4) | 1.00305 (19) | 0.62596 (19) | 0.0499 (7) | |
C1A | 0.8431 (5) | 0.9457 (2) | 0.5494 (2) | 0.0447 (8) | |
H1AA | 0.8999 | 0.9213 | 0.4999 | 0.054* | |
C2A | 1.0919 (5) | 0.9560 (2) | 0.7307 (3) | 0.0416 (8) | |
C3A | 1.2520 (5) | 0.9211 (2) | 0.7145 (3) | 0.0462 (8) | |
H3AA | 1.2599 | 0.9045 | 0.6468 | 0.055* | |
C4A | 1.4000 (5) | 0.9111 (2) | 0.8010 (3) | 0.0517 (9) | |
H4AA | 1.5099 | 0.8876 | 0.7927 | 0.062* | |
C5A | 1.3830 (5) | 0.9365 (2) | 0.9004 (3) | 0.0529 (9) | |
C6A | 1.2256 (5) | 0.9728 (3) | 0.9189 (3) | 0.0513 (9) | |
H6AA | 1.2195 | 0.9902 | 0.9867 | 0.062* | |
C7A | 1.0774 (5) | 0.9822 (2) | 0.8322 (2) | 0.0448 (7) | |
C8A | 0.7857 (5) | 0.9987 (2) | 0.6965 (3) | 0.0475 (8) | |
C9A | 0.6656 (5) | 0.9695 (2) | 0.5327 (3) | 0.0442 (8) | |
C10A | 0.5183 (4) | 0.9645 (2) | 0.4339 (2) | 0.0419 (7) | |
C11A | 0.5515 (5) | 0.9338 (2) | 0.3389 (3) | 0.0512 (9) | |
H11A | 0.6680 | 0.9147 | 0.3376 | 0.061* | |
C12A | 0.4119 (5) | 0.9315 (2) | 0.2468 (3) | 0.0535 (9) | |
H12A | 0.4354 | 0.9107 | 0.1840 | 0.064* | |
C13A | 0.2379 (5) | 0.9599 (2) | 0.2466 (2) | 0.0469 (8) | |
C14A | 0.2027 (5) | 0.9902 (2) | 0.3400 (2) | 0.0489 (8) | |
H14A | 0.0862 | 1.0094 | 0.3410 | 0.059* | |
C15A | 0.3434 (5) | 0.9915 (2) | 0.4323 (2) | 0.0485 (8) | |
H15A | 0.3189 | 1.0113 | 0.4952 | 0.058* | |
C16A | −0.0712 (5) | 0.9810 (3) | 0.1471 (3) | 0.0736 (11) | |
H16A | −0.1439 | 0.9797 | 0.0749 | 0.110* | |
H16B | −0.0730 | 1.0446 | 0.1755 | 0.110* | |
H16C | −0.1196 | 0.9361 | 0.1886 | 0.110* | |
S1B | 0.44615 (11) | 0.65085 (6) | 0.87504 (6) | 0.0551 (2) | |
F1B | 1.1185 (3) | 0.74352 (15) | 1.02571 (15) | 0.0727 (6) | |
O1B | −0.3004 (4) | 0.72079 (18) | 0.19408 (19) | 0.0642 (7) | |
N1B | 0.5109 (4) | 0.70099 (17) | 0.6977 (2) | 0.0420 (7) | |
N2B | 0.2174 (4) | 0.6637 (2) | 0.6678 (2) | 0.0471 (7) | |
C1B | 0.4345 (5) | 0.7183 (2) | 0.5919 (2) | 0.0449 (8) | |
H1BA | 0.4932 | 0.7411 | 0.5425 | 0.054* | |
C2B | 0.6794 (4) | 0.71310 (19) | 0.7725 (2) | 0.0379 (7) | |
C3B | 0.8426 (5) | 0.7428 (2) | 0.7558 (3) | 0.0450 (8) | |
H3BA | 0.8528 | 0.7565 | 0.6878 | 0.054* | |
C4B | 0.9899 (5) | 0.7517 (2) | 0.8425 (3) | 0.0496 (8) | |
H4BA | 1.1021 | 0.7708 | 0.8336 | 0.060* | |
C5B | 0.9712 (5) | 0.7326 (2) | 0.9415 (3) | 0.0500 (9) | |
C6B | 0.8146 (5) | 0.7013 (2) | 0.9615 (2) | 0.0496 (8) | |
H6BA | 0.8072 | 0.6879 | 1.0301 | 0.060* | |
C7B | 0.6651 (4) | 0.6903 (2) | 0.8739 (2) | 0.0427 (8) | |
C8B | 0.3730 (4) | 0.6691 (2) | 0.7379 (2) | 0.0444 (7) | |
C9B | 0.2543 (5) | 0.6953 (2) | 0.5740 (2) | 0.0417 (8) | |
C10B | 0.1091 (5) | 0.7020 (2) | 0.4758 (3) | 0.0423 (8) | |
C11B | 0.1394 (5) | 0.7359 (2) | 0.3813 (2) | 0.0506 (8) | |
H11B | 0.2560 | 0.7550 | 0.3802 | 0.061* | |
C12B | 0.0013 (5) | 0.7417 (3) | 0.2897 (3) | 0.0554 (9) | |
H12B | 0.0248 | 0.7652 | 0.2279 | 0.066* | |
C13B | −0.1737 (5) | 0.7124 (2) | 0.2892 (2) | 0.0472 (8) | |
C14B | −0.2083 (5) | 0.6788 (2) | 0.3807 (3) | 0.0505 (9) | |
H14B | −0.3251 | 0.6595 | 0.3811 | 0.061* | |
C15B | −0.0671 (5) | 0.6739 (2) | 0.4732 (2) | 0.0489 (8) | |
H15B | −0.0915 | 0.6512 | 0.5351 | 0.059* | |
C16B | −0.4794 (5) | 0.6850 (3) | 0.1868 (3) | 0.0671 (10) | |
H16D | −0.5526 | 0.6914 | 0.1151 | 0.101* | |
H16E | −0.5333 | 0.7213 | 0.2334 | 0.101* | |
H16F | −0.4724 | 0.6184 | 0.2071 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0490 (6) | 0.0787 (6) | 0.0442 (5) | 0.0094 (4) | 0.0113 (4) | −0.0105 (4) |
F1A | 0.0579 (17) | 0.1000 (16) | 0.0651 (15) | 0.0116 (13) | −0.0074 (12) | −0.0116 (12) |
O1A | 0.0589 (18) | 0.0840 (17) | 0.0428 (13) | 0.0008 (14) | 0.0007 (12) | −0.0052 (12) |
N1A | 0.0385 (18) | 0.0436 (14) | 0.0396 (15) | 0.0029 (12) | 0.0104 (12) | 0.0004 (12) |
N2A | 0.0422 (17) | 0.0633 (18) | 0.0431 (14) | 0.0056 (14) | 0.0093 (12) | −0.0042 (12) |
C1A | 0.053 (2) | 0.0441 (17) | 0.0376 (17) | −0.0003 (14) | 0.0128 (15) | 0.0002 (12) |
C2A | 0.045 (2) | 0.0360 (16) | 0.0452 (18) | 0.0008 (15) | 0.0144 (15) | 0.0016 (13) |
C3A | 0.050 (2) | 0.0409 (16) | 0.0503 (19) | 0.0022 (15) | 0.0175 (17) | −0.0004 (14) |
C4A | 0.041 (2) | 0.0457 (18) | 0.068 (3) | 0.0004 (16) | 0.0143 (19) | −0.0006 (16) |
C5A | 0.047 (2) | 0.053 (2) | 0.053 (2) | −0.0049 (16) | 0.0036 (17) | −0.0041 (15) |
C6A | 0.052 (2) | 0.055 (2) | 0.0446 (19) | −0.0062 (17) | 0.0102 (16) | −0.0063 (16) |
C7A | 0.049 (2) | 0.0423 (16) | 0.0439 (18) | −0.0001 (15) | 0.0130 (15) | −0.0045 (14) |
C8A | 0.043 (2) | 0.054 (2) | 0.0478 (19) | 0.0048 (16) | 0.0155 (15) | −0.0044 (15) |
C9A | 0.047 (2) | 0.0408 (16) | 0.0464 (19) | −0.0011 (15) | 0.0158 (17) | 0.0000 (14) |
C10A | 0.046 (2) | 0.0383 (15) | 0.0397 (17) | −0.0018 (14) | 0.0077 (14) | 0.0010 (13) |
C11A | 0.050 (2) | 0.056 (2) | 0.048 (2) | 0.0050 (16) | 0.0141 (17) | 0.0003 (16) |
C12A | 0.058 (3) | 0.064 (2) | 0.0387 (18) | 0.0004 (17) | 0.0125 (17) | −0.0032 (15) |
C13A | 0.049 (2) | 0.0462 (16) | 0.0408 (18) | −0.0026 (16) | 0.0035 (16) | 0.0037 (14) |
C14A | 0.045 (2) | 0.0543 (19) | 0.0470 (18) | 0.0061 (15) | 0.0106 (15) | −0.0025 (14) |
C15A | 0.052 (2) | 0.0525 (19) | 0.0405 (18) | −0.0007 (15) | 0.0112 (16) | −0.0036 (14) |
C16A | 0.052 (3) | 0.094 (3) | 0.064 (2) | 0.005 (2) | −0.0045 (18) | 0.001 (2) |
S1B | 0.0432 (5) | 0.0785 (6) | 0.0425 (4) | −0.0067 (4) | 0.0093 (4) | 0.0115 (4) |
F1B | 0.0498 (13) | 0.0932 (14) | 0.0636 (13) | −0.0094 (11) | −0.0058 (10) | 0.0097 (12) |
O1B | 0.0554 (18) | 0.0845 (18) | 0.0456 (13) | −0.0021 (14) | 0.0009 (12) | 0.0108 (13) |
N1B | 0.0400 (18) | 0.0464 (15) | 0.0398 (15) | −0.0022 (12) | 0.0106 (13) | −0.0020 (12) |
N2B | 0.0417 (17) | 0.0549 (16) | 0.0433 (14) | −0.0053 (14) | 0.0085 (12) | 0.0012 (13) |
C1B | 0.051 (2) | 0.0484 (18) | 0.0355 (16) | −0.0038 (15) | 0.0121 (15) | 0.0004 (13) |
C2B | 0.0339 (19) | 0.0384 (15) | 0.0403 (16) | 0.0028 (13) | 0.0077 (13) | −0.0004 (12) |
C3B | 0.044 (2) | 0.0478 (17) | 0.0433 (18) | 0.0049 (15) | 0.0117 (16) | 0.0020 (15) |
C4B | 0.045 (2) | 0.0444 (17) | 0.062 (2) | −0.0003 (14) | 0.0171 (17) | 0.0073 (15) |
C5B | 0.041 (2) | 0.0504 (18) | 0.051 (2) | 0.0024 (16) | −0.0016 (16) | 0.0024 (16) |
C6B | 0.047 (2) | 0.0557 (18) | 0.0439 (17) | 0.0006 (15) | 0.0078 (15) | 0.0057 (14) |
C7B | 0.038 (2) | 0.0452 (17) | 0.0450 (18) | 0.0004 (14) | 0.0106 (15) | 0.0011 (14) |
C8B | 0.045 (2) | 0.0483 (17) | 0.0424 (17) | −0.0028 (15) | 0.0157 (15) | 0.0026 (14) |
C9B | 0.045 (2) | 0.0432 (16) | 0.0373 (17) | −0.0023 (14) | 0.0109 (15) | −0.0033 (13) |
C10B | 0.044 (2) | 0.0404 (16) | 0.0413 (17) | −0.0024 (14) | 0.0083 (15) | −0.0021 (13) |
C11B | 0.046 (2) | 0.0609 (19) | 0.0445 (18) | −0.0049 (16) | 0.0112 (16) | 0.0048 (16) |
C12B | 0.059 (3) | 0.065 (2) | 0.0424 (19) | −0.0071 (19) | 0.0131 (17) | 0.0091 (18) |
C13B | 0.052 (2) | 0.0453 (17) | 0.0399 (17) | 0.0036 (15) | 0.0037 (15) | 0.0005 (13) |
C14B | 0.041 (2) | 0.061 (2) | 0.049 (2) | −0.0031 (16) | 0.0096 (16) | −0.0005 (16) |
C15B | 0.051 (2) | 0.0530 (18) | 0.0424 (17) | −0.0059 (15) | 0.0106 (15) | 0.0026 (14) |
C16B | 0.048 (2) | 0.081 (3) | 0.060 (2) | 0.0003 (19) | −0.0078 (17) | −0.0053 (18) |
S1A—C8A | 1.737 (4) | S1B—C8B | 1.748 (3) |
S1A—C7A | 1.746 (3) | S1B—C7B | 1.758 (3) |
F1A—C5A | 1.353 (4) | F1B—C5B | 1.359 (3) |
O1A—C13A | 1.376 (4) | O1B—C13B | 1.364 (3) |
O1A—C16A | 1.415 (4) | O1B—C16B | 1.430 (4) |
N1A—C8A | 1.369 (4) | N1B—C8B | 1.364 (4) |
N1A—C1A | 1.394 (4) | N1B—C1B | 1.373 (4) |
N1A—C2A | 1.400 (4) | N1B—C2B | 1.405 (3) |
N2A—C8A | 1.311 (4) | N2B—C8B | 1.296 (4) |
N2A—C9A | 1.401 (4) | N2B—C9B | 1.396 (4) |
C1A—C9A | 1.352 (5) | C1B—C9B | 1.368 (4) |
C1A—H1AA | 0.9300 | C1B—H1BA | 0.9300 |
C2A—C3A | 1.378 (5) | C2B—C3B | 1.379 (4) |
C2A—C7A | 1.405 (4) | C2B—C7B | 1.392 (4) |
C3A—C4A | 1.379 (4) | C3B—C4B | 1.375 (4) |
C3A—H3AA | 0.9300 | C3B—H3BA | 0.9300 |
C4A—C5A | 1.382 (5) | C4B—C5B | 1.362 (5) |
C4A—H4AA | 0.9300 | C4B—H4BA | 0.9300 |
C5A—C6A | 1.378 (5) | C5B—C6B | 1.357 (5) |
C6A—C7A | 1.380 (4) | C6B—C7B | 1.396 (4) |
C6A—H6AA | 0.9300 | C6B—H6BA | 0.9300 |
C9A—C10A | 1.473 (4) | C9B—C10B | 1.461 (4) |
C10A—C15A | 1.378 (4) | C10B—C15B | 1.389 (5) |
C10A—C11A | 1.394 (4) | C10B—C11B | 1.394 (4) |
C11A—C12A | 1.382 (4) | C11B—C12B | 1.372 (4) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.381 (5) | C12B—C13B | 1.391 (5) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.379 (4) | C13B—C14B | 1.370 (4) |
C14A—C15A | 1.388 (4) | C14B—C15B | 1.393 (4) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9600 | C16B—H16D | 0.9600 |
C16A—H16B | 0.9600 | C16B—H16E | 0.9600 |
C16A—H16C | 0.9600 | C16B—H16F | 0.9600 |
C8A—S1A—C7A | 90.01 (16) | C8B—S1B—C7B | 89.75 (16) |
C13A—O1A—C16A | 117.9 (3) | C13B—O1B—C16B | 117.8 (3) |
C8A—N1A—C1A | 105.7 (3) | C8B—N1B—C1B | 106.1 (3) |
C8A—N1A—C2A | 114.7 (3) | C8B—N1B—C2B | 115.2 (2) |
C1A—N1A—C2A | 139.4 (3) | C1B—N1B—C2B | 138.4 (3) |
C8A—N2A—C9A | 103.7 (3) | C8B—N2B—C9B | 104.2 (3) |
C9A—C1A—N1A | 105.8 (3) | C9B—C1B—N1B | 105.9 (3) |
C9A—C1A—H1AA | 127.1 | C9B—C1B—H1BA | 127.1 |
N1A—C1A—H1AA | 127.1 | N1B—C1B—H1BA | 127.1 |
C3A—C2A—N1A | 127.8 (3) | C3B—C2B—C7B | 121.0 (3) |
C3A—C2A—C7A | 121.7 (3) | C3B—C2B—N1B | 128.5 (3) |
N1A—C2A—C7A | 110.4 (3) | C7B—C2B—N1B | 110.4 (3) |
C2A—C3A—C4A | 118.5 (3) | C4B—C3B—C2B | 118.1 (3) |
C2A—C3A—H3AA | 120.8 | C4B—C3B—H3BA | 120.9 |
C4A—C3A—H3AA | 120.8 | C2B—C3B—H3BA | 120.9 |
C3A—C4A—C5A | 119.1 (3) | C5B—C4B—C3B | 119.9 (3) |
C3A—C4A—H4AA | 120.5 | C5B—C4B—H4BA | 120.1 |
C5A—C4A—H4AA | 120.5 | C3B—C4B—H4BA | 120.1 |
F1A—C5A—C6A | 118.2 (3) | C6B—C5B—F1B | 117.5 (3) |
F1A—C5A—C4A | 118.0 (3) | C6B—C5B—C4B | 124.0 (3) |
C6A—C5A—C4A | 123.8 (3) | F1B—C5B—C4B | 118.5 (3) |
C5A—C6A—C7A | 117.0 (3) | C5B—C6B—C7B | 116.5 (3) |
C5A—C6A—H6AA | 121.5 | C5B—C6B—H6BA | 121.7 |
C7A—C6A—H6AA | 121.5 | C7B—C6B—H6BA | 121.7 |
C6A—C7A—C2A | 120.0 (3) | C2B—C7B—C6B | 120.3 (3) |
C6A—C7A—S1A | 127.2 (2) | C2B—C7B—S1B | 112.9 (2) |
C2A—C7A—S1A | 112.7 (2) | C6B—C7B—S1B | 126.8 (2) |
N2A—C8A—N1A | 113.5 (3) | N2B—C8B—N1B | 113.6 (3) |
N2A—C8A—S1A | 134.4 (2) | N2B—C8B—S1B | 134.6 (2) |
N1A—C8A—S1A | 112.1 (3) | N1B—C8B—S1B | 111.7 (2) |
C1A—C9A—N2A | 111.3 (3) | C1B—C9B—N2B | 110.2 (3) |
C1A—C9A—C10A | 129.0 (3) | C1B—C9B—C10B | 129.1 (3) |
N2A—C9A—C10A | 119.6 (3) | N2B—C9B—C10B | 120.7 (3) |
C15A—C10A—C11A | 117.9 (3) | C15B—C10B—C11B | 117.1 (3) |
C15A—C10A—C9A | 120.8 (3) | C15B—C10B—C9B | 120.5 (3) |
C11A—C10A—C9A | 121.3 (3) | C11B—C10B—C9B | 122.4 (3) |
C12A—C11A—C10A | 120.2 (3) | C12B—C11B—C10B | 121.6 (3) |
C12A—C11A—H11A | 119.9 | C12B—C11B—H11B | 119.2 |
C10A—C11A—H11A | 119.9 | C10B—C11B—H11B | 119.2 |
C13A—C12A—C11A | 121.0 (3) | C11B—C12B—C13B | 120.2 (3) |
C13A—C12A—H12A | 119.5 | C11B—C12B—H12B | 119.9 |
C11A—C12A—H12A | 119.5 | C13B—C12B—H12B | 119.9 |
O1A—C13A—C14A | 124.5 (3) | O1B—C13B—C14B | 124.8 (3) |
O1A—C13A—C12A | 116.0 (3) | O1B—C13B—C12B | 115.4 (3) |
C14A—C13A—C12A | 119.5 (3) | C14B—C13B—C12B | 119.8 (3) |
C13A—C14A—C15A | 119.1 (3) | C13B—C14B—C15B | 119.4 (3) |
C13A—C14A—H14A | 120.4 | C13B—C14B—H14B | 120.3 |
C15A—C14A—H14A | 120.4 | C15B—C14B—H14B | 120.3 |
C10A—C15A—C14A | 122.2 (3) | C10B—C15B—C14B | 122.0 (3) |
C10A—C15A—H15A | 118.9 | C10B—C15B—H15B | 119.0 |
C14A—C15A—H15A | 118.9 | C14B—C15B—H15B | 119.0 |
O1A—C16A—H16A | 109.5 | O1B—C16B—H16D | 109.5 |
O1A—C16A—H16B | 109.5 | O1B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
O1A—C16A—H16C | 109.5 | O1B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
C8A—N1A—C1A—C9A | 0.9 (3) | C8B—N1B—C1B—C9B | −0.4 (3) |
C2A—N1A—C1A—C9A | 176.0 (3) | C2B—N1B—C1B—C9B | −174.7 (3) |
C8A—N1A—C2A—C3A | 177.2 (3) | C8B—N1B—C2B—C3B | 179.1 (3) |
C1A—N1A—C2A—C3A | 2.4 (5) | C1B—N1B—C2B—C3B | −6.9 (5) |
C8A—N1A—C2A—C7A | 1.0 (3) | C8B—N1B—C2B—C7B | −0.9 (3) |
C1A—N1A—C2A—C7A | −173.8 (3) | C1B—N1B—C2B—C7B | 173.1 (3) |
N1A—C2A—C3A—C4A | −175.2 (3) | C7B—C2B—C3B—C4B | −1.6 (4) |
C7A—C2A—C3A—C4A | 0.6 (4) | N1B—C2B—C3B—C4B | 178.4 (3) |
C2A—C3A—C4A—C5A | −0.1 (4) | C2B—C3B—C4B—C5B | −0.9 (4) |
C3A—C4A—C5A—F1A | 178.4 (3) | C3B—C4B—C5B—C6B | 2.3 (5) |
C3A—C4A—C5A—C6A | −0.8 (5) | C3B—C4B—C5B—F1B | −179.0 (3) |
F1A—C5A—C6A—C7A | −178.1 (3) | F1B—C5B—C6B—C7B | −179.8 (3) |
C4A—C5A—C6A—C7A | 1.1 (5) | C4B—C5B—C6B—C7B | −1.1 (5) |
C5A—C6A—C7A—C2A | −0.6 (4) | C3B—C2B—C7B—C6B | 2.8 (4) |
C5A—C6A—C7A—S1A | 177.5 (3) | N1B—C2B—C7B—C6B | −177.2 (2) |
C3A—C2A—C7A—C6A | −0.3 (4) | C3B—C2B—C7B—S1B | −178.2 (2) |
N1A—C2A—C7A—C6A | 176.2 (3) | N1B—C2B—C7B—S1B | 1.8 (3) |
C3A—C2A—C7A—S1A | −178.6 (2) | C5B—C6B—C7B—C2B | −1.4 (4) |
N1A—C2A—C7A—S1A | −2.1 (3) | C5B—C6B—C7B—S1B | 179.7 (3) |
C8A—S1A—C7A—C6A | −176.1 (3) | C8B—S1B—C7B—C2B | −1.7 (2) |
C8A—S1A—C7A—C2A | 2.1 (2) | C8B—S1B—C7B—C6B | 177.1 (3) |
C9A—N2A—C8A—N1A | 0.4 (3) | C9B—N2B—C8B—N1B | −0.7 (3) |
C9A—N2A—C8A—S1A | −176.8 (3) | C9B—N2B—C8B—S1B | 175.4 (3) |
C1A—N1A—C8A—N2A | −0.8 (3) | C1B—N1B—C8B—N2B | 0.7 (3) |
C2A—N1A—C8A—N2A | −177.3 (2) | C2B—N1B—C8B—N2B | 176.5 (2) |
C1A—N1A—C8A—S1A | 177.0 (2) | C1B—N1B—C8B—S1B | −176.3 (2) |
C2A—N1A—C8A—S1A | 0.5 (3) | C2B—N1B—C8B—S1B | −0.4 (3) |
C7A—S1A—C8A—N2A | 175.8 (3) | C7B—S1B—C8B—N2B | −174.9 (3) |
C7A—S1A—C8A—N1A | −1.4 (2) | C7B—S1B—C8B—N1B | 1.2 (2) |
N1A—C1A—C9A—N2A | −0.7 (3) | N1B—C1B—C9B—N2B | 0.0 (3) |
N1A—C1A—C9A—C10A | 179.1 (3) | N1B—C1B—C9B—C10B | 178.6 (3) |
C8A—N2A—C9A—C1A | 0.2 (3) | C8B—N2B—C9B—C1B | 0.4 (3) |
C8A—N2A—C9A—C10A | −179.6 (3) | C8B—N2B—C9B—C10B | −178.3 (2) |
C1A—C9A—C10A—C15A | 179.6 (3) | C1B—C9B—C10B—C15B | 179.4 (3) |
N2A—C9A—C10A—C15A | −0.6 (4) | N2B—C9B—C10B—C15B | −2.2 (4) |
C1A—C9A—C10A—C11A | −1.4 (5) | C1B—C9B—C10B—C11B | −0.4 (5) |
N2A—C9A—C10A—C11A | 178.4 (3) | N2B—C9B—C10B—C11B | 178.1 (3) |
C15A—C10A—C11A—C12A | 0.4 (4) | C15B—C10B—C11B—C12B | 0.3 (5) |
C9A—C10A—C11A—C12A | −178.7 (3) | C9B—C10B—C11B—C12B | 180.0 (3) |
C10A—C11A—C12A—C13A | 0.3 (5) | C10B—C11B—C12B—C13B | −0.7 (5) |
C16A—O1A—C13A—C14A | −1.6 (5) | C16B—O1B—C13B—C14B | −5.1 (4) |
C16A—O1A—C13A—C12A | 178.3 (3) | C16B—O1B—C13B—C12B | 175.4 (3) |
C11A—C12A—C13A—O1A | 179.6 (3) | C11B—C12B—C13B—O1B | −179.7 (3) |
C11A—C12A—C13A—C14A | −0.5 (5) | C11B—C12B—C13B—C14B | 0.7 (5) |
O1A—C13A—C14A—C15A | 179.9 (3) | O1B—C13B—C14B—C15B | −179.8 (3) |
C12A—C13A—C14A—C15A | 0.0 (5) | C12B—C13B—C14B—C15B | −0.3 (5) |
C11A—C10A—C15A—C14A | −0.9 (4) | C11B—C10B—C15B—C14B | 0.2 (4) |
C9A—C10A—C15A—C14A | 178.2 (3) | C9B—C10B—C15B—C14B | −179.6 (3) |
C13A—C14A—C15A—C10A | 0.7 (4) | C13B—C14B—C15B—C10B | −0.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O1Ai | 0.93 | 2.53 | 3.367 (5) | 149 |
C6B—H6BA···O1Bi | 0.93 | 2.52 | 3.382 (4) | 153 |
Symmetry code: (i) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H11FN2OS |
Mr | 298.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 7.6120 (13), 13.883 (2), 13.049 (2) |
β (°) | 105.117 (3) |
V (Å3) | 1331.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.31 × 0.30 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.926, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20506, 7656, 4268 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.116, 1.00 |
No. of reflections | 7656 |
No. of parameters | 381 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.25 |
Absolute structure | Flack (1983), 3649 Friedel pairs |
Absolute structure parameter | 0.00 (8) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O1Ai | 0.9300 | 2.5300 | 3.367 (5) | 149.00 |
C6B—H6BA···O1Bi | 0.9300 | 2.5200 | 3.382 (4) | 153.00 |
Symmetry code: (i) x+1, y, z+1. |
Footnotes
‡Thomson Reuters Researcher ID: A-3561-2009.
Acknowledgements
HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. KU and BKS gratefully acknowledge P. A. College of Engineering, Mangalore, for providing facilities to carry out the research work.
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.
Benzothiazoles are very important bicyclic ring compounds which are of great interest because of their biological activities. The substituted benzothiazole derivatives have emerged as significant components in various diversified therapeutic applications. Literature review has shown that benzothiazoles and their derivatives show considerable properties, including potent inhibition of human immunodeficiency virus type 1 (HIV-1), replication by HIV-1 protease (Yaseen et al., 2006), antitumor (Kini et al., 2007), anthelmintic (Munirajasekhar et al., 2011) analgesic and anti-inflammatory (Gurupadayya et al., 2008), antimalarial (Bowyer et al., 2007), antifungal (Mittal et al., 2007), anticandidous (Pozas et al., 2005) and various CNS activities (Rana et al., 2008). Imidazole has become an important part of many pharmaceuticals. Synthetic imidazoles are present in many fungicides and antifungals (Saha et al., 2000), antiprotozoal and antihypertensive medications. Imidazole is part of the theophylline molecule, found in tea leaves and coffee beans, that stimulates the central nervous system. It is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities (Katritzky & Rees, 1984). The structure of a related compound 7-Chloro-3-phenylbenzo[4,5]thiazolo-[2,3-c][1,2,4] triazole has been reported by Fun et al., 2011.
In continuation of our research investigation, a new fused imidazo[2,1-b]thiazole derivative was prepared by the reaction of flurobenzothiazole amine with 4-methoxy phenacyl bromide under microwave irradiation at 130 °C and its crystal structure is reported here.
The asymmetric unit of the title compound consists of two crystallographically independent molecules, (A & B), as shown in Fig. 1. The bond lengths and angles of molecules A and B agree with each other and are within normal ranges (Allen et al., 1987). The benzothiazole units are essentially planar with maximum deviations of 0.038 (2) Å for atom N1A (molecule A) and 0.045 (3) Å for atom C7B (molecule B). The dihedral angles that the central benzothiazole (S1/N1,N2/C1,C2,C7–C9) ring makes with the two terminal phenyl (C2–C7/C10–C15) rings in the two independent molecules are 4.87 (13)° : 0.64 (12)° for molecule A and 4.04 (12)° : 3.67 (12)° for molecule B.
In the crystal structure (Fig. 2), the molecules are connected via weak intermolecular C—H···O hydrogen bonds forming one-dimensional supramolecular chains along the c-axis.