organic compounds
4-Hydroxy-6-methyl-3-[3-(thiophen-2-yl)acryloyl]-2H-pyran-2-one
aLaboratoire d'Électrochimie des Matériaux Moléculaires et Complexes, Centre Univeresitaire de B.B.A., Algeria, bEcole Normale Superieure de Constantine, 25000 Constantine, Algeria, cUniversité 20 Aout 1955, 21000 Skikda, Algeria, and dLaboratoire de Chimie Biomimétique des Métaux de Transition, Institut de Chimie, Strasbourg, France
*Correspondence e-mail: boufas_sihem@yahoo.fr
The title compound, C13H10O4S, crystallizes with two molecules in the in which the rings make dihedral angles of 3.9 (1) and 6.0 (1)°; this planarity is due in part to the presence of an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring in each molecule. Both molecules represent E isomers with respect to the central C=C bond. In the crystal, molecules are linked by C—H⋯O interactions into a three-dimensional network.
Related literature
For pharmacological properties of et al. (1994); Dinkova-Kostova et al. (1998); Ram et al. (2000); Kidwai et al. (2001); Ballesteros et al. (1995). For their non-linear optical properties, see: Fichou et al. (1988) and for their importance, see: Tomazela et al. (2000). For precursors in the synthesis of see: Drexler & Amiridis (2003). For graph-set notation, see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).
see: WattenbergExperimental
Crystal data
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Refinement
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Data collection: COLLECT (Nonius, 2002); cell DENZO-SMN (Otwinowski & Minor, 1997); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and PARST (Nardelli, 1995).
Supporting information
10.1107/S1600536813003826/ld2095sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813003826/ld2095Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813003826/ld2095Isup3.cml
Dehydroacetic acid (0.168 g, 1 mmol) in 1 ml of piperidine was added to thiofene-2-carboxaldehyde (0.112 g, 1 mmol) of in 25 ml of chloroform and then refluxed with stirring under nitrogen atmosphere for 3 days. After that, 5–7 ml of the chloroform-water azeotrope mixture were removed by simple distillation. The product were obtained by slow evaporation of the remaining chloroform and washed with ethyl acetate (2x5ml), then it was recrystalized from dichlromethane and dried under vaccum in dissicator for 24 h (yield 63%). Melting point: 150 °C.
C—H and O—H hydrogen atoms were placed in calculated positions and refined as riding atoms with C—H distances of 0.93 Å with Uiso(H) = 1.2Ueq(C) and O—H distances of 0.82 Å, with Uiso(H) = 1.2Ueq(N).
The methyl H atoms were constrained to an ideal geometry (C—H = 0.96 Å) with Uiso(H) = 1.2Ueq(C), but were allowed to rotate freely about the C—C bonds.
Data collection: COLLECT (Nonius, 2002); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and PARST (Nardelli, 1995).Fig. 1. The structure of the title compound in 50% probability ellipsoids. | |
Fig. 2. Part of the crystal structure of (I), showing the formation of S(6) rings with dashed bleu lines. C—H···O Hydrogen bonds are shown as red dashed lines. Hydrogen atoms not involved in the motif have been omitted for clarity. |
C13H10O4S | Z = 4 |
Mr = 262.27 | F(000) = 544 |
Triclinic, P1 | Dx = 1.459 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0737 (4) Å | Cell parameters from 102968 reflections |
b = 9.9428 (5) Å | θ = 2.9–27.5° |
c = 15.0887 (8) Å | µ = 0.27 mm−1 |
α = 87.770 (1)° | T = 293 K |
β = 87.779 (3)° | Block, brown |
γ = 80.678 (4)° | 0.5 × 0.4 × 0.2 mm |
V = 1193.70 (11) Å3 |
Nonius KappaCCD diffractometer | 6954 independent reflections |
Radiation source: Enraf Nonius FR590 | 5295 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 9 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
CCD rotation images, thin slices scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −13→13 |
Tmin = 0.875, Tmax = 0.947 | l = −21→21 |
25106 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0755P)2 + 0.747P] where P = (Fo2 + 2Fc2)/3 |
6954 reflections | (Δ/σ)max = 0.001 |
326 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C13H10O4S | γ = 80.678 (4)° |
Mr = 262.27 | V = 1193.70 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.0737 (4) Å | Mo Kα radiation |
b = 9.9428 (5) Å | µ = 0.27 mm−1 |
c = 15.0887 (8) Å | T = 293 K |
α = 87.770 (1)° | 0.5 × 0.4 × 0.2 mm |
β = 87.779 (3)° |
Nonius KappaCCD diffractometer | 6954 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 5295 reflections with I > 2σ(I) |
Tmin = 0.875, Tmax = 0.947 | Rint = 0.036 |
25106 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.97 e Å−3 |
6954 reflections | Δρmin = −0.30 e Å−3 |
326 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S2 | 0.46904 (7) | 0.30887 (5) | 0.54080 (4) | 0.03338 (14) | |
S1 | 0.88623 (7) | 0.31448 (5) | 0.04850 (4) | 0.03337 (14) | |
O2 | 0.57005 (19) | −0.13416 (14) | −0.19215 (9) | 0.0300 (3) | |
O4 | 0.7556 (2) | −0.19703 (16) | 0.10407 (10) | 0.0363 (3) | |
O3 | 0.6293 (2) | −0.36848 (16) | 0.03371 (11) | 0.0417 (4) | |
H33 | 0.6698 | −0.3296 | 0.0725 | 0.063* | |
O5 | 0.99995 (19) | −0.14198 (15) | 0.30123 (10) | 0.0311 (3) | |
O8 | 0.8369 (2) | −0.18574 (16) | 0.60568 (10) | 0.0351 (3) | |
O7 | 1.0375 (2) | −0.35666 (17) | 0.53507 (11) | 0.0423 (4) | |
H77 | 0.9792 | −0.3154 | 0.5741 | 0.063* | |
O6 | 0.8273 (2) | 0.03013 (16) | 0.35590 (11) | 0.0415 (4) | |
O1 | 0.6537 (2) | 0.04135 (16) | −0.13444 (11) | 0.0400 (4) | |
C17 | 0.9154 (2) | −0.15767 (19) | 0.45626 (13) | 0.0247 (4) | |
C4 | 0.6592 (2) | −0.15850 (18) | −0.04027 (12) | 0.0237 (4) | |
C1 | 0.5297 (3) | −0.2617 (2) | −0.18823 (14) | 0.0301 (4) | |
C5 | 0.6115 (3) | −0.2898 (2) | −0.03754 (14) | 0.0281 (4) | |
C2 | 0.5453 (3) | −0.3400 (2) | −0.11347 (15) | 0.0324 (4) | |
H2 | 0.5133 | −0.4258 | −0.1114 | 0.039* | |
C9 | 0.9119 (3) | 0.1816 (2) | 0.12658 (13) | 0.0296 (4) | |
C3 | 0.6316 (2) | −0.0752 (2) | −0.12040 (13) | 0.0263 (4) | |
C22 | 0.5087 (3) | 0.1834 (2) | 0.62381 (13) | 0.0277 (4) | |
C14 | 1.0980 (3) | −0.2661 (2) | 0.30732 (14) | 0.0300 (4) | |
C25 | 0.3326 (3) | 0.4103 (2) | 0.60884 (17) | 0.0385 (5) | |
H25 | 0.275 | 0.4954 | 0.5916 | 0.046* | |
C19 | 0.8208 (2) | −0.1100 (2) | 0.53485 (13) | 0.0269 (4) | |
C18 | 0.9056 (3) | −0.0812 (2) | 0.37306 (13) | 0.0275 (4) | |
C16 | 1.0214 (3) | −0.2859 (2) | 0.46114 (14) | 0.0291 (4) | |
C10 | 0.9849 (3) | 0.2172 (2) | 0.20074 (14) | 0.0346 (5) | |
H10 | 1.0118 | 0.1582 | 0.2493 | 0.042* | |
C6 | 0.7344 (2) | −0.1158 (2) | 0.03667 (13) | 0.0269 (4) | |
C21 | 0.6233 (3) | 0.0584 (2) | 0.61300 (14) | 0.0291 (4) | |
H21 | 0.6401 | −0.0005 | 0.6624 | 0.035* | |
C23 | 0.4178 (3) | 0.2221 (2) | 0.69960 (14) | 0.0325 (4) | |
H23 | 0.4214 | 0.1682 | 0.7515 | 0.039* | |
C20 | 0.7082 (2) | 0.0192 (2) | 0.53790 (13) | 0.0281 (4) | |
H20 | 0.6947 | 0.0754 | 0.4871 | 0.034* | |
C15 | 1.1117 (3) | −0.3389 (2) | 0.38406 (15) | 0.0321 (4) | |
H15 | 1.18 | −0.4237 | 0.3869 | 0.038* | |
C7 | 0.7857 (3) | 0.0168 (2) | 0.04186 (14) | 0.0307 (4) | |
H7 | 0.77 | 0.0782 | −0.0063 | 0.037* | |
C13 | 0.4714 (3) | −0.2980 (3) | −0.27485 (17) | 0.0445 (6) | |
H13A | 0.4448 | −0.3887 | −0.2704 | 0.067* | |
H13B | 0.5586 | −0.2938 | −0.3195 | 0.067* | |
H13C | 0.3732 | −0.2349 | −0.2907 | 0.067* | |
C24 | 0.3181 (3) | 0.3516 (2) | 0.69120 (16) | 0.0374 (5) | |
H24 | 0.25 | 0.3927 | 0.7369 | 0.045* | |
C12 | 0.9682 (3) | 0.4177 (2) | 0.11694 (16) | 0.0383 (5) | |
H12 | 0.9796 | 0.5076 | 0.1023 | 0.046* | |
C26 | 1.1800 (3) | −0.3059 (3) | 0.22020 (16) | 0.0414 (5) | |
H26A | 1.2477 | −0.3943 | 0.2264 | 0.062* | |
H26B | 1.2496 | −0.2403 | 0.2004 | 0.062* | |
H26C | 1.0955 | −0.3088 | 0.1776 | 0.062* | |
C11 | 1.0149 (3) | 0.3533 (2) | 0.19538 (15) | 0.0377 (5) | |
H11 | 1.0615 | 0.3944 | 0.2405 | 0.045* | |
C8 | 0.8554 (3) | 0.0524 (2) | 0.11472 (14) | 0.0318 (4) | |
H8 | 0.8688 | −0.0112 | 0.1618 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0367 (3) | 0.0325 (3) | 0.0306 (3) | −0.0057 (2) | −0.0036 (2) | 0.0072 (2) |
S1 | 0.0414 (3) | 0.0313 (3) | 0.0277 (3) | −0.0072 (2) | −0.0059 (2) | 0.00652 (19) |
O2 | 0.0375 (8) | 0.0285 (7) | 0.0251 (7) | −0.0092 (6) | −0.0039 (6) | 0.0036 (5) |
O4 | 0.0454 (9) | 0.0397 (8) | 0.0232 (7) | −0.0067 (7) | −0.0021 (6) | 0.0069 (6) |
O3 | 0.0556 (10) | 0.0352 (8) | 0.0370 (9) | −0.0179 (7) | −0.0078 (7) | 0.0151 (7) |
O5 | 0.0372 (8) | 0.0296 (7) | 0.0260 (7) | −0.0057 (6) | 0.0022 (6) | 0.0035 (6) |
O8 | 0.0415 (9) | 0.0384 (8) | 0.0233 (7) | −0.0013 (7) | −0.0040 (6) | 0.0069 (6) |
O7 | 0.0514 (10) | 0.0375 (8) | 0.0315 (8) | 0.0106 (7) | −0.0033 (7) | 0.0088 (6) |
O6 | 0.0513 (10) | 0.0331 (8) | 0.0341 (8) | 0.0057 (7) | 0.0066 (7) | 0.0135 (6) |
O1 | 0.0604 (11) | 0.0289 (7) | 0.0338 (8) | −0.0165 (7) | −0.0139 (7) | 0.0116 (6) |
C17 | 0.0250 (9) | 0.0250 (8) | 0.0243 (9) | −0.0052 (7) | −0.0034 (7) | 0.0028 (7) |
C4 | 0.0244 (9) | 0.0227 (8) | 0.0235 (9) | −0.0036 (6) | 0.0014 (7) | 0.0035 (7) |
C1 | 0.0271 (9) | 0.0295 (9) | 0.0345 (11) | −0.0064 (8) | −0.0013 (8) | −0.0029 (8) |
C5 | 0.0283 (9) | 0.0257 (9) | 0.0301 (10) | −0.0057 (7) | 0.0017 (7) | 0.0060 (7) |
C2 | 0.0319 (10) | 0.0256 (9) | 0.0407 (12) | −0.0084 (8) | −0.0013 (8) | 0.0013 (8) |
C9 | 0.0350 (10) | 0.0291 (9) | 0.0247 (9) | −0.0054 (8) | −0.0039 (8) | 0.0043 (7) |
C3 | 0.0277 (9) | 0.0269 (9) | 0.0243 (9) | −0.0048 (7) | −0.0020 (7) | 0.0033 (7) |
C22 | 0.0283 (9) | 0.0285 (9) | 0.0267 (9) | −0.0068 (7) | −0.0028 (7) | 0.0037 (7) |
C14 | 0.0300 (10) | 0.0272 (9) | 0.0349 (11) | −0.0105 (8) | 0.0010 (8) | −0.0028 (8) |
C25 | 0.0370 (12) | 0.0305 (10) | 0.0457 (13) | 0.0024 (9) | −0.0084 (10) | 0.0001 (9) |
C19 | 0.0272 (9) | 0.0281 (9) | 0.0264 (9) | −0.0072 (7) | −0.0043 (7) | 0.0017 (7) |
C18 | 0.0287 (9) | 0.0271 (9) | 0.0268 (9) | −0.0059 (7) | 0.0006 (7) | 0.0035 (7) |
C16 | 0.0298 (10) | 0.0286 (9) | 0.0287 (10) | −0.0044 (8) | −0.0058 (8) | 0.0044 (8) |
C10 | 0.0419 (12) | 0.0382 (11) | 0.0255 (10) | −0.0130 (9) | −0.0025 (8) | 0.0048 (8) |
C6 | 0.0261 (9) | 0.0274 (9) | 0.0258 (9) | −0.0003 (7) | 0.0011 (7) | 0.0009 (7) |
C21 | 0.0301 (10) | 0.0296 (9) | 0.0279 (10) | −0.0064 (8) | −0.0030 (8) | 0.0044 (8) |
C23 | 0.0341 (11) | 0.0337 (10) | 0.0292 (10) | −0.0050 (8) | −0.0010 (8) | 0.0020 (8) |
C20 | 0.0271 (9) | 0.0293 (9) | 0.0278 (10) | −0.0045 (7) | −0.0031 (7) | 0.0040 (7) |
C15 | 0.0309 (10) | 0.0272 (9) | 0.0372 (11) | −0.0019 (8) | −0.0014 (8) | −0.0007 (8) |
C7 | 0.0330 (10) | 0.0292 (9) | 0.0293 (10) | −0.0046 (8) | −0.0019 (8) | 0.0049 (8) |
C13 | 0.0505 (14) | 0.0449 (13) | 0.0406 (13) | −0.0123 (11) | −0.0105 (11) | −0.0052 (10) |
C24 | 0.0352 (11) | 0.0369 (11) | 0.0383 (12) | 0.0001 (9) | 0.0007 (9) | −0.0060 (9) |
C12 | 0.0479 (13) | 0.0301 (10) | 0.0389 (12) | −0.0129 (9) | −0.0022 (10) | 0.0023 (9) |
C26 | 0.0508 (14) | 0.0373 (11) | 0.0379 (12) | −0.0143 (10) | 0.0099 (10) | −0.0064 (9) |
C11 | 0.0468 (13) | 0.0400 (11) | 0.0293 (11) | −0.0156 (10) | −0.0020 (9) | −0.0037 (9) |
C8 | 0.0346 (11) | 0.0321 (10) | 0.0274 (10) | −0.0034 (8) | 0.0013 (8) | 0.0042 (8) |
S2—C25 | 1.708 (2) | C22—C21 | 1.435 (3) |
S2—C22 | 1.735 (2) | C14—C15 | 1.340 (3) |
S1—C12 | 1.707 (2) | C14—C26 | 1.487 (3) |
S1—C9 | 1.728 (2) | C25—C24 | 1.361 (3) |
O2—C1 | 1.358 (2) | C25—H25 | 0.93 |
O2—C3 | 1.396 (2) | C19—C20 | 1.450 (3) |
O4—C6 | 1.273 (2) | C16—C15 | 1.421 (3) |
O3—C5 | 1.303 (2) | C10—C11 | 1.412 (3) |
O3—H33 | 0.82 | C10—H10 | 0.93 |
O5—C14 | 1.356 (3) | C6—C7 | 1.450 (3) |
O5—C18 | 1.399 (3) | C21—C20 | 1.339 (3) |
O8—C19 | 1.281 (2) | C21—H21 | 0.93 |
O7—C16 | 1.295 (2) | C23—C24 | 1.408 (3) |
O7—H77 | 0.82 | C23—H23 | 0.93 |
O6—C18 | 1.206 (2) | C20—H20 | 0.93 |
O1—C3 | 1.210 (2) | C15—H15 | 0.93 |
C17—C16 | 1.417 (3) | C7—C8 | 1.339 (3) |
C17—C19 | 1.439 (3) | C7—H7 | 0.93 |
C17—C18 | 1.440 (3) | C13—H13A | 0.96 |
C4—C5 | 1.418 (3) | C13—H13B | 0.96 |
C4—C6 | 1.440 (3) | C13—H13C | 0.96 |
C4—C3 | 1.443 (3) | C24—H24 | 0.93 |
C1—C2 | 1.344 (3) | C12—C11 | 1.360 (3) |
C1—C13 | 1.483 (3) | C12—H12 | 0.93 |
C5—C2 | 1.423 (3) | C26—H26A | 0.96 |
C2—H2 | 0.93 | C26—H26B | 0.96 |
C9—C10 | 1.369 (3) | C26—H26C | 0.96 |
C9—C8 | 1.450 (3) | C11—H11 | 0.93 |
C22—C23 | 1.368 (3) | C8—H8 | 0.93 |
C25—S2—C22 | 91.77 (11) | C9—C10—C11 | 112.55 (19) |
C12—S1—C9 | 91.51 (10) | C9—C10—H10 | 123.7 |
C1—O2—C3 | 123.26 (16) | C11—C10—H10 | 123.7 |
C5—O3—H33 | 109.5 | O4—C6—C4 | 118.89 (18) |
C14—O5—C18 | 123.20 (16) | O4—C6—C7 | 117.96 (18) |
C16—O7—H77 | 109.5 | C4—C6—C7 | 123.15 (17) |
C16—C17—C19 | 118.31 (17) | C20—C21—C22 | 125.64 (19) |
C16—C17—C18 | 118.88 (18) | C20—C21—H21 | 117.2 |
C19—C17—C18 | 122.81 (17) | C22—C21—H21 | 117.2 |
C5—C4—C6 | 118.36 (17) | C22—C23—C24 | 113.3 (2) |
C5—C4—C3 | 118.30 (17) | C22—C23—H23 | 123.4 |
C6—C4—C3 | 123.34 (17) | C24—C23—H23 | 123.4 |
C2—C1—O2 | 121.62 (19) | C21—C20—C19 | 120.74 (18) |
C2—C1—C13 | 127.2 (2) | C21—C20—H20 | 119.6 |
O2—C1—C13 | 111.21 (19) | C19—C20—H20 | 119.6 |
O3—C5—C4 | 121.18 (18) | C14—C15—C16 | 119.67 (19) |
O3—C5—C2 | 118.20 (18) | C14—C15—H15 | 120.2 |
C4—C5—C2 | 120.61 (18) | C16—C15—H15 | 120.2 |
C1—C2—C5 | 119.11 (18) | C8—C7—C6 | 121.25 (19) |
C1—C2—H2 | 120.4 | C8—C7—H7 | 119.4 |
C5—C2—H2 | 120.4 | C6—C7—H7 | 119.4 |
C10—C9—C8 | 125.57 (19) | C1—C13—H13A | 109.5 |
C10—C9—S1 | 111.12 (16) | C1—C13—H13B | 109.5 |
C8—C9—S1 | 123.26 (15) | H13A—C13—H13B | 109.5 |
O1—C3—O2 | 114.36 (17) | C1—C13—H13C | 109.5 |
O1—C3—C4 | 128.67 (18) | H13A—C13—H13C | 109.5 |
O2—C3—C4 | 116.96 (16) | H13B—C13—H13C | 109.5 |
C23—C22—C21 | 125.88 (19) | C25—C24—C23 | 112.6 (2) |
C23—C22—S2 | 110.40 (15) | C25—C24—H24 | 123.7 |
C21—C22—S2 | 123.71 (16) | C23—C24—H24 | 123.7 |
C15—C14—O5 | 121.52 (19) | C11—C12—S1 | 112.14 (17) |
C15—C14—C26 | 127.2 (2) | C11—C12—H12 | 123.9 |
O5—C14—C26 | 111.28 (19) | S1—C12—H12 | 123.9 |
C24—C25—S2 | 111.97 (17) | C14—C26—H26A | 109.5 |
C24—C25—H25 | 124 | C14—C26—H26B | 109.5 |
S2—C25—H25 | 124 | H26A—C26—H26B | 109.5 |
O8—C19—C17 | 118.31 (18) | C14—C26—H26C | 109.5 |
O8—C19—C20 | 118.39 (19) | H26A—C26—H26C | 109.5 |
C17—C19—C20 | 123.31 (17) | H26B—C26—H26C | 109.5 |
O6—C18—O5 | 114.24 (18) | C12—C11—C10 | 112.6 (2) |
O6—C18—C17 | 129.1 (2) | C12—C11—H11 | 123.7 |
O5—C18—C17 | 116.70 (17) | C10—C11—H11 | 123.7 |
O7—C16—C17 | 121.05 (19) | C7—C8—C9 | 125.68 (19) |
O7—C16—C15 | 118.95 (19) | C7—C8—H8 | 117.2 |
C17—C16—C15 | 120.00 (18) | C9—C8—H8 | 117.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H33···O4 | 0.82 | 1.68 | 2.421 (2) | 150 |
O7—H77···O8 | 0.82 | 1.65 | 2.400 (2) | 150 |
C8—H8···O5 | 0.93 | 2.60 | 3.481 (3) | 159 |
C10—H10···O6 | 0.93 | 2.59 | 3.280 (3) | 132 |
C10—H10···O8i | 0.93 | 2.59 | 3.288 (3) | 132 |
C13—H13C···O6ii | 0.96 | 2.58 | 3.507 (3) | 164 |
C23—H23···O4iii | 0.93 | 2.56 | 3.245 (3) | 131 |
C25—H25···O7iv | 0.93 | 2.38 | 3.240 (3) | 153 |
C26—H26B···O1v | 0.96 | 2.41 | 3.338 (3) | 163 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x−1, y+1, z; (v) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C13H10O4S |
Mr | 262.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.0737 (4), 9.9428 (5), 15.0887 (8) |
α, β, γ (°) | 87.770 (1), 87.779 (3), 80.678 (4) |
V (Å3) | 1193.70 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.5 × 0.4 × 0.2 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.875, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25106, 6954, 5295 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.157, 1.06 |
No. of reflections | 6954 |
No. of parameters | 326 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −0.30 |
Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H33···O4 | 0.82 | 1.68 | 2.421 (2) | 150 |
O7—H77···O8 | 0.82 | 1.65 | 2.400 (2) | 150 |
C8—H8···O5 | 0.93 | 2.60 | 3.481 (3) | 159 |
C10—H10···O6 | 0.93 | 2.59 | 3.280 (3) | 132 |
C10—H10···O8i | 0.93 | 2.59 | 3.288 (3) | 132 |
C13—H13C···O6ii | 0.96 | 2.58 | 3.507 (3) | 164 |
C23—H23···O4iii | 0.93 | 2.56 | 3.245 (3) | 131 |
C25—H25···O7iv | 0.93 | 2.38 | 3.240 (3) | 153 |
C26—H26B···O1v | 0.96 | 2.41 | 3.338 (3) | 163 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x−1, y+1, z; (v) −x+2, −y, −z. |
Acknowledgements
This work was supported by Université Farhat Abbes DZ-19000. Sétif, Algeria.
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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.
Chalcones are an important group of natural products (Tomazela, et al., 2000), which have various pharmacological properties. Some chalcones possess anticancer (Wattenberg, et al., 1994, Dinkova-Kostova, et al., 1998), antimalarial (Ram, et al., 2000), antimicrobial (Kidwai, et al., 2001) and anti-inflammatory (Ballesteros, et al., 1995) activities. Chalcones also serve as precursors in the syntheses of different classes of flavonoids (Drexler, et al., 2003). Chalcone derivatives are also a class of organic compounds with excellent NLO properties (Fichou, et al., 1988), much better than those observed in inorganic crystals. Furthermore, several α,β-unsaturated ketones have been found to exhibit biological activity. In this paper, we report a structure containing both thiazole and α,β-unsaturated ketone moieties in one molecule. The crystals do not exhibit second-order nonlinear optical properties as they crystallize in a centrosymmetric space group.
The title compound (Fig. 1) exists in an E configuration with respect to the C7—C8 and C20—C21 double bonds. 6-membered rings adopt a planar conformation. In the cyclic moiety with O2 atom, the r.m.s. deviation for the non-H atoms is 0.0154 Å, with the maximum deviation of C4 from the mean plane being 0.0222 (14) Å. In the moiety with O5 atom, the r.m.s. deviation for the non-H atoms is 0.0063 Å, with the maximum deviation of C17 from the mean plane -0.0105 (13) Å. The thiazole rings are also planar with a r.m.s deviation for non-H atoms of 0.0076 Å (ring with S1) & 0.0020 Å (ring with S2) with a maximum deviation of C9 from the mean plane being (-0.0107 (13)) Å and a maximum deviation of C24 from the mean plane of 0.0029 (15) Å respectively. With respect to the C7—C8 and C20—C21 bonds, the atom pairs C6/C9, H7/H8 and C19/C20, H20/H21 are all trans, shown by the value of (-0.05 (14)°) for O8—C21—C20—C19 and 0.42 (15)°) for C6—C7—C8—O4 - 0.42 (15)° torsion angle. The double-bond character of the bond between C7 and C8 is deduced from the short bond distance [1.339 (3) Å]. The value in the other molecule is 1.339 (3) Å for C20/C21]. All bond lengths and angles in (I) have normal values (Allen, et al. 1987).
The two rings derived from DHA and 2-Acetyl-thiophene; exhibit coplanar geometry, the coplanarity of the two rings is due to the presence of intramolecular O7—H77···O8 and O3—H33···O4 hydrogen bond. This interactions generate an S(6) ring motif (Bernstein, et al. 1995). The overall structure is held by seven C—H···O interactions, forming a three- dimensional network. (Fig. 2). Among others, C25—H25···O7 interaction is the strongest one.