organic compounds
(2E)-2-(1,3-Benzothiazol-2-yl)-3-(dimethylamino)prop-2-enenitrile
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Sccience, Minia University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
The molecular conformation of title compound, C12H11N3S, is almost planar [maximum deviation = 0.063 (2) Å]; an intramolecular C—H⋯N hydrogen bond is noted. In the crystal, molecules interact with each other via π–π stacking interactions between thiazole rings [centroid–centroid distance = 3.7475 (9) Å] and methyl-H⋯π(C6) interactions, forming columns along the a axis.
CCDC reference: 975725
Related literature
For various biological activities (e.g. anti-tumour, anti-inflammatory, anti-viral, etc.) of benzothiazole compounds, see: Selvam et al. (2011); Sanja & Cvetkovic (2011); Alang et al. (2010); Pal et al. (2011); Sharma et al. (2010); El-Shaaer et al. (1997); Gupta & Raat (2010); Hutchinson et al. (2002); Gong et al. (2004); Hutchinson et al. (2003); Geronikaki & Theophilidis (1992); Vicini et al. (1990); Das et al. (2003); Klose et al. (1983); Satsangi et al. (1983).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 975725
https://doi.org/10.1107/S1600536813033266/tk5279sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033266/tk5279Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033266/tk5279Isup3.cml
A mixture of 1,3-benzothiazol-2-ylacetnitrile (174 mg, 1 mmol) and dimethylformamide-dimethylacetal (119 mg, 1 mmol) were taken in acetic acid (10 ml). The reaction mixture was refluxed and monitored by TLC until completion after 8 h. The reaction mixture was allowed to cool at ambient temperature and poured into ice water. The solid product was collected by filtration and recrystallized from ethanol to afford the title compound in 88% yield. Single crystals suitable for X-ray analysis were grown up on slow evaporation of ethanolic solution of the title compound at room temperature over three days. M.pt: 441–443 K.
All H-atoms were refined using a riding model with C—H = 0.93 Å and Uiso=1.2eq (C) for aromatic-H atoms, and C—H = 0.96 Å and Uiso = 1.5Ueq (C) for methyl-H atoms.
It is well known that the thiazolyl group is of great importance in biological systems. In recent years, there has been considerable interest in the synthesis of substituted benzothiazolyl compounds due to their pharmacological properties such as anti-fungal (Selvam et al., 2011; Sanja & Cvetkovic, 2011), anti-viral (Alang et al., 2010; Pal et al., 2011), anti-bacterial (Sharma et al., 2010; El-Shaaer et al., 1997), analgesic (Gupta & Raat, 2010), anti-tumour (Hutchinson et al., 2002) and anti-tuberculosis (Gong et al., 2004; Hutchinson et al., 2003) activities. Moreover, such compounds have been also found to have a potent local anaesthetic activity (Geronikaki & Theophilidis, 1992; Vicini et al., 1990). Anti-inflammatory, analgesic, and anti-pyretic activities for some thiazolyl and benzothiazolyl derivatives are also known (Das et al., 2003; Klose et al., 1983; Satsangi et al., 1983). Based on the above and following to our ongoing studies in synthesis of bio-active
the title compound has been prepared as a precursor for further study.As shown in Fig. 1, title compound (I) has an almost planar conformation for non-hydrogen atoms with a maximum deviation of -0.063 (2) Å for C6.
The π-π stacking interactions [Cg1···Cg1(1 - x, 1 - y, 1 - z) = 3.7475 (9) Å; where Cg1 is a centroid of the five-membered (S1/N1/C1/C2/C7) thiazole ring of the 1,3-benzothiazole ring system] between the centroids of thiazole rings of the adjacent molecules. The has no classical hydrogen bonds. Figs. 2 show the molecular packing of (I) viewed along the a direction.
is stabilized byFor various biological activities (e.g. anti-tumour, anti-inflammatory, anti-viral, etc.) of benzothiazole compounds, see: Selvam et al. (2011); Sanja & Cvetkovic (2011); Alang et al. (2010); Pal et al. (2011); Sharma et al. (2010); El-Shaaer et al. (1997); Gupta & Raat (2010); Hutchinson et al. (2002); Gong et al. (2004); Hutchinson et al. (2003); Geronikaki & Theophilidis (1992); Vicini et al. (1990); Das et al. (2003); Klose et al. (1983); Satsangi et al. (1983).
Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell
CrysAlis PRO (Oxford Diffraction, 2013); data reduction: CrysAlis PRO (Oxford Diffraction, 2013); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C12H11N3S | F(000) = 480 |
Mr = 229.31 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 1971 reflections |
a = 7.3785 (2) Å | θ = 4.4–72.7° |
b = 20.1801 (4) Å | µ = 2.32 mm−1 |
c = 8.2706 (2) Å | T = 293 K |
β = 112.947 (4)° | Block, purple |
V = 1134.03 (6) Å3 | 0.26 × 0.20 × 0.09 mm |
Z = 4 |
Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer | 2195 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 1971 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.016 |
ω scans | θmax = 72.7°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013) | h = −7→9 |
Tmin = 0.584, Tmax = 0.818 | k = −16→25 |
4062 measured reflections | l = −10→8 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1211P] where P = (Fo2 + 2Fc2)/3 |
2195 reflections | (Δ/σ)max = 0.002 |
147 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C12H11N3S | V = 1134.03 (6) Å3 |
Mr = 229.31 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.3785 (2) Å | µ = 2.32 mm−1 |
b = 20.1801 (4) Å | T = 293 K |
c = 8.2706 (2) Å | 0.26 × 0.20 × 0.09 mm |
β = 112.947 (4)° |
Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer | 2195 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013) | 1971 reflections with I > 2σ(I) |
Tmin = 0.584, Tmax = 0.818 | Rint = 0.016 |
4062 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.25 e Å−3 |
2195 reflections | Δρmin = −0.26 e Å−3 |
147 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.11365 (6) | 0.50492 (2) | 0.23607 (5) | 0.0475 (1) | |
N1 | 0.24456 (18) | 0.46002 (6) | 0.55620 (16) | 0.0427 (4) | |
N2 | 0.3152 (3) | 0.66200 (8) | 0.3024 (2) | 0.0704 (6) | |
N3 | 0.5370 (2) | 0.62896 (8) | 0.81666 (18) | 0.0544 (4) | |
C1 | 0.0527 (2) | 0.42447 (7) | 0.26748 (18) | 0.0417 (4) | |
C2 | 0.1371 (2) | 0.40931 (7) | 0.44773 (19) | 0.0403 (4) | |
C3 | 0.1078 (2) | 0.34624 (8) | 0.5022 (2) | 0.0491 (5) | |
C4 | −0.0040 (3) | 0.30080 (8) | 0.3794 (2) | 0.0518 (5) | |
C5 | −0.0886 (2) | 0.31692 (9) | 0.2020 (2) | 0.0516 (5) | |
C6 | −0.0608 (2) | 0.37875 (9) | 0.1440 (2) | 0.0501 (5) | |
C7 | 0.2450 (2) | 0.51233 (7) | 0.46445 (18) | 0.0388 (4) | |
C8 | 0.3437 (2) | 0.57454 (7) | 0.53589 (19) | 0.0411 (4) | |
C9 | 0.4385 (2) | 0.57944 (8) | 0.7160 (2) | 0.0459 (5) | |
C10 | 0.5596 (3) | 0.69358 (10) | 0.7510 (3) | 0.0643 (6) | |
C11 | 0.6221 (4) | 0.62098 (14) | 1.0073 (3) | 0.0817 (8) | |
C12 | 0.3318 (2) | 0.62455 (8) | 0.4120 (2) | 0.0491 (5) | |
H3 | 0.16340 | 0.33490 | 0.62050 | 0.0590* | |
H4 | −0.02320 | 0.25870 | 0.41570 | 0.0620* | |
H5 | −0.16480 | 0.28570 | 0.12150 | 0.0620* | |
H6 | −0.11670 | 0.38950 | 0.02530 | 0.0600* | |
H9 | 0.43210 | 0.54140 | 0.77700 | 0.0550* | |
H10A | 0.62640 | 0.68910 | 0.67250 | 0.0960* | |
H10B | 0.63510 | 0.72160 | 0.84750 | 0.0960* | |
H10C | 0.43220 | 0.71290 | 0.68920 | 0.0960* | |
H11A | 0.60670 | 0.57590 | 1.03660 | 0.1230* | |
H11B | 0.55600 | 0.64990 | 1.05890 | 0.1230* | |
H11C | 0.75950 | 0.63200 | 1.05180 | 0.1230* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0628 (3) | 0.0411 (2) | 0.0349 (2) | −0.0012 (2) | 0.0150 (2) | 0.0049 (1) |
N1 | 0.0501 (7) | 0.0382 (6) | 0.0408 (6) | 0.0023 (5) | 0.0188 (5) | 0.0008 (5) |
N2 | 0.0975 (13) | 0.0468 (8) | 0.0584 (9) | −0.0053 (8) | 0.0213 (8) | 0.0088 (7) |
N3 | 0.0544 (7) | 0.0575 (8) | 0.0464 (7) | −0.0001 (6) | 0.0144 (6) | −0.0116 (6) |
C1 | 0.0489 (7) | 0.0408 (7) | 0.0378 (7) | 0.0023 (6) | 0.0194 (6) | 0.0037 (6) |
C2 | 0.0457 (7) | 0.0413 (7) | 0.0365 (7) | 0.0036 (6) | 0.0189 (6) | 0.0014 (5) |
C3 | 0.0618 (9) | 0.0453 (8) | 0.0428 (8) | 0.0007 (7) | 0.0231 (7) | 0.0065 (6) |
C4 | 0.0642 (9) | 0.0417 (8) | 0.0567 (9) | −0.0033 (7) | 0.0315 (7) | 0.0019 (7) |
C5 | 0.0575 (9) | 0.0502 (8) | 0.0518 (9) | −0.0093 (7) | 0.0263 (7) | −0.0104 (7) |
C6 | 0.0576 (9) | 0.0546 (9) | 0.0377 (7) | −0.0041 (7) | 0.0180 (6) | −0.0027 (6) |
C7 | 0.0443 (7) | 0.0394 (7) | 0.0336 (7) | 0.0066 (5) | 0.0162 (6) | 0.0018 (5) |
C8 | 0.0457 (7) | 0.0369 (7) | 0.0412 (7) | 0.0041 (6) | 0.0175 (6) | −0.0008 (6) |
C9 | 0.0486 (8) | 0.0454 (8) | 0.0432 (8) | 0.0039 (6) | 0.0173 (6) | −0.0026 (6) |
C10 | 0.0652 (10) | 0.0537 (10) | 0.0699 (11) | −0.0082 (8) | 0.0219 (9) | −0.0178 (9) |
C11 | 0.0848 (15) | 0.0984 (17) | 0.0464 (10) | −0.0053 (13) | 0.0087 (9) | −0.0160 (11) |
C12 | 0.0570 (9) | 0.0379 (7) | 0.0485 (8) | 0.0002 (6) | 0.0165 (7) | −0.0029 (6) |
S1—C1 | 1.7311 (15) | C7—C8 | 1.456 (2) |
S1—C7 | 1.7612 (14) | C8—C9 | 1.380 (2) |
N1—C2 | 1.3878 (19) | C8—C12 | 1.416 (2) |
N1—C7 | 1.3008 (19) | C3—H3 | 0.9300 |
N2—C12 | 1.150 (2) | C4—H4 | 0.9300 |
N3—C9 | 1.322 (2) | C5—H5 | 0.9300 |
N3—C10 | 1.447 (3) | C6—H6 | 0.9300 |
N3—C11 | 1.461 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.407 (2) | C10—H10A | 0.9600 |
C1—C6 | 1.389 (2) | C10—H10B | 0.9600 |
C2—C3 | 1.395 (2) | C10—H10C | 0.9600 |
C3—C4 | 1.378 (2) | C11—H11A | 0.9600 |
C4—C5 | 1.391 (2) | C11—H11B | 0.9600 |
C5—C6 | 1.381 (3) | C11—H11C | 0.9600 |
C1—S1—C7 | 89.15 (7) | C2—C3—H3 | 120.00 |
C2—N1—C7 | 110.61 (12) | C4—C3—H3 | 120.00 |
C9—N3—C10 | 124.08 (15) | C3—C4—H4 | 120.00 |
C9—N3—C11 | 119.72 (17) | C5—C4—H4 | 119.00 |
C10—N3—C11 | 116.13 (18) | C4—C5—H5 | 120.00 |
S1—C1—C2 | 109.23 (10) | C6—C5—H5 | 120.00 |
S1—C1—C6 | 129.06 (12) | C1—C6—H6 | 121.00 |
C2—C1—C6 | 121.71 (14) | C5—C6—H6 | 121.00 |
N1—C2—C1 | 115.46 (13) | N3—C9—H9 | 114.00 |
N1—C2—C3 | 125.84 (13) | C8—C9—H9 | 115.00 |
C1—C2—C3 | 118.70 (13) | N3—C10—H10A | 109.00 |
C2—C3—C4 | 119.52 (14) | N3—C10—H10B | 109.00 |
C3—C4—C5 | 121.02 (16) | N3—C10—H10C | 109.00 |
C4—C5—C6 | 120.77 (15) | H10A—C10—H10B | 109.00 |
C1—C6—C5 | 118.27 (14) | H10A—C10—H10C | 109.00 |
S1—C7—N1 | 115.55 (11) | H10B—C10—H10C | 110.00 |
S1—C7—C8 | 119.17 (10) | N3—C11—H11A | 109.00 |
N1—C7—C8 | 125.28 (13) | N3—C11—H11B | 109.00 |
C7—C8—C9 | 117.55 (13) | N3—C11—H11C | 109.00 |
C7—C8—C12 | 116.15 (13) | H11A—C11—H11B | 109.00 |
C9—C8—C12 | 126.30 (14) | H11A—C11—H11C | 110.00 |
N3—C9—C8 | 131.03 (15) | H11B—C11—H11C | 109.00 |
N2—C12—C8 | 175.21 (17) | ||
C7—S1—C1—C2 | −0.33 (12) | S1—C1—C2—N1 | 0.48 (18) |
C7—S1—C1—C6 | 179.26 (16) | S1—C1—C2—C3 | −179.33 (12) |
C1—S1—C7—C8 | −179.85 (13) | N1—C2—C3—C4 | 179.54 (17) |
C1—S1—C7—N1 | 0.14 (13) | C1—C2—C3—C4 | −0.7 (2) |
C2—N1—C7—C8 | −179.91 (15) | C2—C3—C4—C5 | −0.2 (3) |
C7—N1—C2—C3 | 179.41 (16) | C3—C4—C5—C6 | 0.8 (3) |
C2—N1—C7—S1 | 0.10 (19) | C4—C5—C6—C1 | −0.4 (3) |
C7—N1—C2—C1 | −0.4 (2) | S1—C7—C8—C12 | −2.3 (2) |
C11—N3—C9—C8 | 179.2 (2) | N1—C7—C8—C9 | −2.6 (2) |
C10—N3—C9—C8 | 2.5 (3) | S1—C7—C8—C9 | 177.44 (12) |
C6—C1—C2—C3 | 1.1 (2) | N1—C7—C8—C12 | 177.71 (15) |
C6—C1—C2—N1 | −179.15 (15) | C12—C8—C9—N3 | 0.5 (3) |
S1—C1—C6—C5 | 179.96 (13) | C7—C8—C9—N3 | −179.24 (17) |
C2—C1—C6—C5 | −0.5 (2) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···N1 | 0.93 | 2.44 | 2.851 (2) | 106 |
C10—H10A···Cg1i | 0.96 | 2.77 | 3.549 (2) | 138 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···N1 | 0.93 | 2.44 | 2.851 (2) | 106 |
C10—H10A···Cg1i | 0.96 | 2.77 | 3.549 (2) | 138 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
We thank Manchester Metropolitan University, Erciyes University and Cardiff University for supporting this study.
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.
It is well known that the thiazolyl group is of great importance in biological systems. In recent years, there has been considerable interest in the synthesis of substituted benzothiazolyl compounds due to their pharmacological properties such as anti-fungal (Selvam et al., 2011; Sanja & Cvetkovic, 2011), anti-viral (Alang et al., 2010; Pal et al., 2011), anti-bacterial (Sharma et al., 2010; El-Shaaer et al., 1997), analgesic (Gupta & Raat, 2010), anti-tumour (Hutchinson et al., 2002) and anti-tuberculosis (Gong et al., 2004; Hutchinson et al., 2003) activities. Moreover, such compounds have been also found to have a potent local anaesthetic activity (Geronikaki & Theophilidis, 1992; Vicini et al., 1990). Anti-inflammatory, analgesic, and anti-pyretic activities for some thiazolyl and benzothiazolyl derivatives are also known (Das et al., 2003; Klose et al., 1983; Satsangi et al., 1983). Based on the above and following to our ongoing studies in synthesis of bio-active heterocyclic compounds the title compound has been prepared as a precursor for further study.
As shown in Fig. 1, title compound (I) has an almost planar conformation for non-hydrogen atoms with a maximum deviation of -0.063 (2) Å for C6.
The crystal structure is stabilized by π-π stacking interactions [Cg1···Cg1(1 - x, 1 - y, 1 - z) = 3.7475 (9) Å; where Cg1 is a centroid of the five-membered (S1/N1/C1/C2/C7) thiazole ring of the 1,3-benzothiazole ring system] between the centroids of thiazole rings of the adjacent molecules. The crystal structure has no classical hydrogen bonds. Figs. 2 show the molecular packing of (I) viewed along the a direction.