(E)-3-(4-Methyl­phen­yl)-1-(1,3-thia­zol-2-yl)prop-2-en-1-one

Palaniappan, A.; Arulmozhivarman, A.; Ramachandran, R.; Srinivasan, S.; Senthan, S.

doi:10.1107/S1600536812019575

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1875

doi:10.1107/S1600536812019575

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(E)-3-(4-Methylphenyl)-1-(1,3-thiazol-2-yl)prop-2-en-1-one

Annamalai Palaniappan,^a ^* Arumugam Arulmozhivarman,^a Rajamanickam Ramachandran,^b Subramanian Srinivasan ^a and Sivakolunthu Senthan ^a

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, and ^bDepartment of Image Science and Engineering, Pukyong National University, Busan 608 737, Republic of Korea
^*Correspondence e-mail: synorgramu@gmail.com

(Received 20 February 2012; accepted 1 May 2012; online 26 May 2012)

In the title chalcone, C₁₃H₁₁NOS, derived from the condensation of p-tolualdehyde and 1-(1,3-thiazol-2-yl)ethanone, the olefine group has a trans configuration. No classical hydrogen bonding is present in the crystal structure.

Related literature

For background to thiazoles, see: Fontecave et al. (2003 ); Kleemann et al. (2001 ) and for their biological activity, see: Bharti et al. (2010 ); Bell et al. (1995 ); Cortes et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₁NOS
M_r = 229.29
Monoclinic, P 2₁ /c
a = 13.9486 (9) Å
b = 11.1773 (8) Å
c = 7.4579 (5) Å
β = 102.061 (4)°
V = 1137.08 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.949, T_max = 0.949
10320 measured reflections
2808 independent reflections
2070 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.118
S = 1.05
2808 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019575/ez2285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019575/ez2285Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019575/ez2285Isup3.cml

checkCIF report

Comment top

Molecules which possess both sulphur and nitrogen atoms exhibit universal and crucial roles in living organisms (Fontecave et al., 2003), with thiazoles and their derivatives being an important class of heterocyclic compounds (Kleemann et al., 2001). Analogues of these are present in several drugs with a wide range of biological properties, such as antibacterial (Bharti et al., 2010), antiviral (Bell et al., 1995) and anticancer (Cortes et al., 2007). Our research has been focused towards finding new therapeutic agents, using thiazole compounds. Similarly, several α,β-unsaturated ketones have been found to have good biological activity. Therefore, in this paper we report both the thiazole and α,β-unsaturated ketone moieties in one molecule. The title compound (Fig. 1) exists in an E configuration with respect to the C7-C8 double bond. Both phenyl and thiazole rings adopt planar orientations and there is no classical hydrogen bonding found.

Related literature top

For background to thiazoles, see: Fontecave et al. (2003); Kleemann et al. (2001) and for their biological activity, see: Bharti, et al. (2010); Bell et al. (1995); Cortes et al. (2007).

Experimental top

To an aqueous ethanolic solution of p-tolualdehyde (0.01 mol) and 2-acetylthiazole (0.01 mol), a sodium hydroxide solution was added slowly and stirred until a precipitate formed. The obtained solid was filtered and washed well with water. Single crystals were grown by the slow evaporation technique using ethanol as solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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).

Figures top

Fig. 1. The ORTEP representation of title compound showing the atom numbering scheme and ellipsoids at the 50% probability level.

(E)-3-(4-Methylphenyl)-1-(1,3-thiazol-2-yl)prop-2-en-1-one top

Crystal data top

C₁₃H₁₁NOS	Z = 4
M_r = 229.29	F(000) = 480
Monoclinic, P2₁/c	D_x = 1.339 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.9486 (9) Å	µ = 0.26 mm⁻¹
b = 11.1773 (8) Å	T = 293 K
c = 7.4579 (5) Å	Prism, colorless
β = 102.061 (4)°	0.20 × 0.20 × 0.20 mm
V = 1137.08 (13) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	2070 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 28.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −18→17
T_min = 0.949, T_max = 0.949	k = −11→14
10320 measured reflections	l = −9→9

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0598P)² + 0.1832P] where P = (F_o² + 2F_c²)/3
2808 reflections	(Δ/σ)_max = 0.001
153 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₁NOS	V = 1137.08 (13) Å³
M_r = 229.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.9486 (9) Å	µ = 0.26 mm⁻¹
b = 11.1773 (8) Å	T = 293 K
c = 7.4579 (5) Å	0.20 × 0.20 × 0.20 mm
β = 102.061 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2808 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2070 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.949	R_int = 0.027
10320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.23 e Å⁻³
2808 reflections	Δρ_min = −0.24 e Å⁻³
153 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.98502 (3)	0.17057 (5)	1.16674 (6)	0.05963 (18)
O1	0.82353 (10)	−0.00430 (12)	1.0300 (2)	0.0721 (4)
N1	0.84607 (10)	0.31056 (13)	1.0198 (2)	0.0540 (4)
C1	0.53219 (10)	0.08303 (13)	0.72422 (19)	0.0380 (3)
C7	0.62986 (11)	0.05556 (15)	0.8309 (2)	0.0425 (3)
C4	0.34124 (11)	0.13769 (15)	0.5336 (2)	0.0451 (4)
C10	0.86817 (11)	0.19796 (15)	1.0453 (2)	0.0440 (4)
C2	0.51393 (11)	0.18190 (13)	0.6090 (2)	0.0420 (3)
H2	0.5657	0.2309	0.5948	0.050*
C8	0.70403 (11)	0.13124 (16)	0.8719 (2)	0.0471 (4)
C3	0.42049 (11)	0.20835 (15)	0.5155 (2)	0.0458 (4)
H3	0.4102	0.2748	0.4388	0.055*
C6	0.45308 (11)	0.01025 (14)	0.7382 (2)	0.0451 (4)
H6	0.4635	−0.0578	0.8113	0.054*
C9	0.79948 (11)	0.09785 (15)	0.9842 (2)	0.0476 (4)
C5	0.35920 (12)	0.03767 (15)	0.6448 (2)	0.0497 (4)
H5	0.3074	−0.0119	0.6570	0.060*
C13	0.23967 (13)	0.16866 (19)	0.4303 (3)	0.0681 (5)
H4C	0.2421	0.2405	0.3608	0.102*
H4A	0.1977	0.1809	0.5156	0.102*
H4B	0.2145	0.1043	0.3487	0.102*
C12	0.92396 (14)	0.37879 (19)	1.1005 (3)	0.0646 (5)
H12	0.9216	0.4619	1.0966	0.078*
C11	1.00462 (14)	0.31959 (19)	1.1861 (3)	0.0622 (5)
H11	1.0625	0.3554	1.2469	0.075*
H7	0.6378 (13)	−0.0218 (18)	0.877 (2)	0.059 (5)*
H8	0.6995 (14)	0.2095 (18)	0.835 (3)	0.066 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0395 (2)	0.0771 (4)	0.0562 (3)	0.0054 (2)	−0.00395 (18)	0.0080 (2)
O1	0.0545 (7)	0.0519 (8)	0.1003 (11)	0.0082 (6)	−0.0058 (7)	0.0108 (7)
N1	0.0422 (7)	0.0531 (9)	0.0628 (9)	0.0023 (6)	0.0019 (6)	−0.0033 (7)
C1	0.0372 (7)	0.0350 (7)	0.0417 (7)	0.0004 (6)	0.0080 (6)	−0.0042 (6)
C7	0.0412 (8)	0.0394 (8)	0.0465 (8)	0.0040 (6)	0.0079 (6)	−0.0002 (7)
C4	0.0383 (7)	0.0472 (9)	0.0476 (8)	0.0011 (6)	0.0040 (6)	−0.0089 (7)
C10	0.0333 (7)	0.0566 (9)	0.0405 (8)	0.0055 (7)	0.0041 (6)	0.0014 (7)
C2	0.0389 (7)	0.0395 (8)	0.0477 (8)	−0.0048 (6)	0.0096 (6)	0.0008 (6)
C8	0.0390 (8)	0.0444 (9)	0.0544 (9)	0.0022 (7)	0.0017 (7)	0.0025 (7)
C3	0.0469 (8)	0.0420 (8)	0.0465 (8)	0.0026 (7)	0.0046 (6)	0.0035 (7)
C6	0.0478 (8)	0.0341 (8)	0.0526 (9)	−0.0041 (6)	0.0083 (7)	0.0028 (7)
C9	0.0378 (7)	0.0517 (10)	0.0519 (9)	0.0049 (7)	0.0059 (6)	0.0019 (7)
C5	0.0410 (8)	0.0459 (9)	0.0619 (10)	−0.0110 (7)	0.0099 (7)	−0.0046 (7)
C13	0.0425 (9)	0.0759 (13)	0.0777 (13)	0.0042 (9)	−0.0063 (9)	−0.0058 (10)
C12	0.0560 (10)	0.0618 (12)	0.0722 (12)	−0.0096 (9)	0.0047 (9)	−0.0107 (10)
C11	0.0466 (9)	0.0835 (14)	0.0530 (10)	−0.0139 (9)	0.0025 (8)	−0.0082 (9)

Geometric parameters (Å, º) top

S1—C11	1.689 (2)	C2—C3	1.376 (2)
S1—C10	1.7185 (15)	C2—H2	0.9300
O1—C9	1.219 (2)	C8—C9	1.465 (2)
N1—C10	1.300 (2)	C8—H8	0.92 (2)
N1—C12	1.360 (2)	C3—H3	0.9300
C1—C2	1.390 (2)	C6—C5	1.383 (2)
C1—C6	1.392 (2)	C6—H6	0.9300
C1—C7	1.460 (2)	C5—H5	0.9300
C7—C8	1.322 (2)	C13—H4C	0.9600
C7—H7	0.929 (19)	C13—H4A	0.9600
C4—C5	1.383 (2)	C13—H4B	0.9600
C4—C3	1.388 (2)	C12—C11	1.346 (3)
C4—C13	1.505 (2)	C12—H12	0.9300
C10—C9	1.482 (2)	C11—H11	0.9300

C11—S1—C10	89.32 (9)	C4—C3—H3	119.4
C10—N1—C12	109.56 (16)	C5—C6—C1	120.99 (14)
C2—C1—C6	117.70 (13)	C5—C6—H6	119.5
C2—C1—C7	122.26 (13)	C1—C6—H6	119.5
C6—C1—C7	120.03 (14)	O1—C9—C8	124.27 (16)
C8—C7—C1	126.00 (15)	O1—C9—C10	119.91 (15)
C8—C7—H7	118.9 (11)	C8—C9—C10	115.81 (14)
C1—C7—H7	115.1 (11)	C6—C5—C4	120.98 (14)
C5—C4—C3	118.03 (14)	C6—C5—H5	119.5
C5—C4—C13	121.73 (16)	C4—C5—H5	119.5
C3—C4—C13	120.21 (16)	C4—C13—H4C	109.5
N1—C10—C9	124.58 (14)	C4—C13—H4A	109.5
N1—C10—S1	114.79 (12)	H4C—C13—H4A	109.5
C9—C10—S1	120.58 (12)	C4—C13—H4B	109.5
C3—C2—C1	121.05 (14)	H4C—C13—H4B	109.5
C3—C2—H2	119.5	H4A—C13—H4B	109.5
C1—C2—H2	119.5	C11—C12—N1	116.45 (19)
C7—C8—C9	122.88 (16)	C11—C12—H12	121.8
C7—C8—H8	122.7 (12)	N1—C12—H12	121.8
C9—C8—H8	114.4 (13)	C12—C11—S1	109.87 (15)
C2—C3—C4	121.20 (15)	C12—C11—H11	125.1
C2—C3—H3	119.4	S1—C11—H11	125.1

C2—C1—C7—C8	19.2 (2)	C7—C1—C6—C5	177.01 (15)
C6—C1—C7—C8	−159.68 (16)	C7—C8—C9—O1	9.7 (3)
C12—N1—C10—C9	176.99 (16)	C7—C8—C9—C10	−169.19 (15)
C12—N1—C10—S1	−0.58 (19)	N1—C10—C9—O1	−172.68 (16)
C11—S1—C10—N1	0.65 (14)	S1—C10—C9—O1	4.8 (2)
C11—S1—C10—C9	−177.02 (14)	N1—C10—C9—C8	6.3 (2)
C6—C1—C2—C3	1.5 (2)	S1—C10—C9—C8	−176.29 (12)
C7—C1—C2—C3	−177.40 (14)	C1—C6—C5—C4	0.6 (2)
C1—C7—C8—C9	178.32 (14)	C3—C4—C5—C6	1.3 (2)
C1—C2—C3—C4	0.3 (2)	C13—C4—C5—C6	179.72 (16)
C5—C4—C3—C2	−1.7 (2)	C10—N1—C12—C11	0.2 (2)
C13—C4—C3—C2	179.84 (16)	N1—C12—C11—S1	0.3 (2)
C2—C1—C6—C5	−2.0 (2)	C10—S1—C11—C12	−0.52 (15)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NOS
M_r	229.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.9486 (9), 11.1773 (8), 7.4579 (5)
β (°)	102.061 (4)
V (Å³)	1137.08 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.949, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	10320, 2808, 2070
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.118, 1.05
No. of reflections	2808
No. of parameters	153
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bell, F. W., Cantrell, A. S., Hogberg, M., Jaskunas, S. R., Johansson, N. G., Jordan, C. L., Kinnick, M. D., Lind, P., Morin, J. M., Noreen, R., Oberg, B., Palkowitz, J. A., Parrish, C. A., Pranc, P., Sahlberg, C., Ternansky, R. J., Vasileff, R. T., Vrang, L., West, S. J., Zhang, H. & Zhou, X. X. (1995). J. Med. Chem. 38, 4929–4936. CrossRef CAS PubMed Web of Science Google Scholar
Bharti, S. K., Nath, G., Tilak, R. & Singh, S. K. (2010). Eur. J. Med. Chem. 45, 651–660. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cortes, J., Rousselot, P., Kim, D. W., Ritchie, E., Hamerschlak, N., Coutre, S., Hochhaus, A., Guilhot, F., Saglio, G., Apperley, J., Ottmann, O., Shah, N., Erben, P., Branford, S., Agarwal, P., Gollerkeri, A. & Baccarani, M. (2007). Blood, 109, 3207–3213. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fontecave, M., Ollagnier-de-Choudens, S. & Mulliez, E. (2003). Chem. Rev. 103, 2149–2166. Web of Science CrossRef PubMed CAS Google Scholar
Kleemann, A., Engel, J., Kutscher, B. & Reichert, D. (2001). Pharmaceutical Substances, 4th ed. Stuttgart: Thieme. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar