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| CRYSTALLOGRAPHIC COMMUNICATIONS |
access(E)-3-(4-Chlorophenyl)-1-(2-thienyl)prop-2-en-1-one
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my
The title compound, C13H9ClOS, adopts an E configuration with respect to the C=C double bond of the propenone unit. The thienyl and benzene rings are slightly twisted from each other, making a dihedral angle of 6.38 (3)°. An intramolecular C—H⋯O hydrogen bond generates an S(5) ring motif. A weak intermolecular C—H⋯O interaction, a short intramolecular S⋯O contact [2.932 (2) Å] and two π–π interactions between the thienyl and benzene rings are observed. The centroid–centroid distances of the π–π interactions are 3.7899 (16) and 3.7891 (16) Å.
Related literature
For related literature on chalcone derivatives, see: Agrinskaya et al. (1999![[Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914-1917.]](../../../../../../logos/arrows/e_arr.gif "Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914-1917.")
); Gu, Ji, Patil & Dharmaprakash (2008); Gu, Ji, Patil, Dharmaprakash & Wang (2008); Fun et al. (2008); Patil et al. (2006); Patil, Dharmaprakash et al. (2007); Patil, Fun et al. (2007). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).
![[Scheme 1]](is2316scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808022782/is2316sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808022782/is2316Isup2.hkl
The compound (I) was synthesized by the condensation of 4-chlorobenzaldehyde (0.01 mol, 1.49 mg) with 2-acetylthiophene (0.01 mol, 1.07 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (10 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. The precipitated compound was recrystallized from N, N-dimethylformamide (DMF).
H atoms were positioned geometrically (C—H = 0.93 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C). The highest peak in the difference Fourier map is located 0.82 Å from atom S1.
Data collection: APEX2 (Bruker, 2005); cell APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).
![[Figure 1]](./is2316fig1thm.gif) | Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. |
![[Figure 2]](./is2316fig2thm.gif) | Fig. 2. The crystal packing of the title compound, viewed along the c axis. |
| C13H9ClOS | F(000) = 512 |
| Mr = 248.71 | Dx = 1.485 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3595 reflections |
| a = 5.7023 (3) Å | θ = 2.8–29.8° |
| b = 13.3576 (8) Å | µ = 0.50 mm−1 |
| c = 14.7017 (10) Å | T = 100 K |
| β = 96.735 (4)° | Needle, colourless |
| V = 1112.09 (12) Å3 | 0.45 × 0.13 × 0.12 mm |
| Z = 4 |
| Bruker SMART APEXII CCD area-detector diffractometer | 3238 independent reflections |
| Radiation source: fine-focus sealed tube | 2546 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.030 |
| ϕ and ω scans | θmax = 30.1°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→8 |
| Tmin = 0.804, Tmax = 0.942 | k = −16→18 |
| 12436 measured reflections | l = −20→15 |
| 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.199 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0986P)2 + 1.8996P] where P = (Fo2 + 2Fc2)/3 |
| 3238 reflections | (Δ/σ)max = 0.001 |
| 145 parameters | Δρmax = 1.76 e Å−3 |
| 0 restraints | Δρmin = −0.49 e Å−3 |
| C13H9ClOS | V = 1112.09 (12) Å3 |
| Mr = 248.71 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 5.7023 (3) Å | µ = 0.50 mm−1 |
| b = 13.3576 (8) Å | T = 100 K |
| c = 14.7017 (10) Å | 0.45 × 0.13 × 0.12 mm |
| β = 96.735 (4)° |
| Bruker SMART APEXII CCD area-detector diffractometer | 3238 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2546 reflections with I > 2σ(I) |
| Tmin = 0.804, Tmax = 0.942 | Rint = 0.030 |
| 12436 measured reflections |
| R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
| wR(F2) = 0.199 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 1.76 e Å−3 |
| 3238 reflections | Δρmin = −0.49 e Å−3 |
| 145 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
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 > σ(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 | 0.90267 (12) | 1.35871 (6) | 0.43901 (5) | 0.0277 (2) | |
| Cl1 | 0.00412 (13) | 0.64087 (5) | 0.29914 (5) | 0.0299 (2) | |
| O1 | 0.9797 (4) | 1.14167 (16) | 0.44334 (16) | 0.0327 (5) | |
| C2 | 0.4870 (5) | 1.4144 (2) | 0.3764 (2) | 0.0293 (6) | |
| H2A | 0.3575 | 1.4550 | 0.3579 | 0.035* | |
| C3 | 0.4820 (5) | 1.3077 (2) | 0.37026 (19) | 0.0224 (5) | |
| H3A | 0.3505 | 1.2703 | 0.3476 | 0.027* | |
| C4 | 0.7018 (5) | 1.2675 (2) | 0.40300 (18) | 0.0223 (5) | |
| C5 | 0.7766 (5) | 1.1625 (2) | 0.4128 (2) | 0.0250 (6) | |
| C6 | 0.5981 (5) | 1.0853 (2) | 0.3844 (2) | 0.0268 (6) | |
| H6A | 0.4539 | 1.1042 | 0.3529 | 0.032* | |
| C7 | 0.6405 (5) | 0.9890 (2) | 0.40334 (19) | 0.0240 (5) | |
| H7A | 0.7868 | 0.9732 | 0.4349 | 0.029* | |
| C8 | 0.4777 (5) | 0.9050 (2) | 0.37894 (18) | 0.0222 (5) | |
| C9 | 0.2473 (5) | 0.9190 (2) | 0.3366 (2) | 0.0248 (6) | |
| H9A | 0.1911 | 0.9837 | 0.3252 | 0.030* | |
| C10 | 0.1021 (5) | 0.8388 (2) | 0.31147 (19) | 0.0238 (5) | |
| H10A | −0.0501 | 0.8491 | 0.2827 | 0.029* | |
| C1 | 0.7028 (5) | 1.4507 (2) | 0.4124 (2) | 0.0301 (6) | |
| H1A | 0.7357 | 1.5184 | 0.4211 | 0.036* | |
| C12 | 0.4120 (5) | 0.7255 (2) | 0.3732 (2) | 0.0259 (6) | |
| H12A | 0.4659 | 0.6607 | 0.3856 | 0.031* | |
| C13 | 0.5557 (5) | 0.8070 (2) | 0.39794 (19) | 0.0238 (5) | |
| H13A | 0.7068 | 0.7965 | 0.4277 | 0.029* | |
| C11 | 0.1866 (5) | 0.7422 (2) | 0.32979 (19) | 0.0224 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0200 (3) | 0.0344 (4) | 0.0281 (4) | −0.0065 (3) | 0.0004 (3) | −0.0013 (3) |
| Cl1 | 0.0258 (4) | 0.0293 (4) | 0.0341 (4) | −0.0077 (3) | 0.0020 (3) | −0.0027 (3) |
| O1 | 0.0221 (10) | 0.0339 (12) | 0.0397 (13) | −0.0002 (8) | −0.0060 (9) | 0.0006 (9) |
| C2 | 0.0217 (13) | 0.0321 (15) | 0.0342 (16) | 0.0004 (11) | 0.0034 (11) | −0.0023 (12) |
| C3 | 0.0171 (11) | 0.0235 (12) | 0.0262 (13) | −0.0011 (9) | 0.0012 (9) | −0.0021 (10) |
| C4 | 0.0174 (11) | 0.0281 (13) | 0.0207 (12) | −0.0040 (10) | 0.0001 (9) | −0.0028 (10) |
| C5 | 0.0201 (12) | 0.0304 (14) | 0.0243 (13) | −0.0007 (10) | 0.0014 (10) | −0.0009 (10) |
| C6 | 0.0191 (12) | 0.0287 (14) | 0.0312 (15) | −0.0021 (10) | −0.0029 (10) | 0.0005 (11) |
| C7 | 0.0172 (11) | 0.0281 (13) | 0.0262 (13) | −0.0028 (10) | 0.0007 (9) | −0.0002 (10) |
| C8 | 0.0173 (11) | 0.0266 (13) | 0.0224 (12) | 0.0009 (9) | 0.0016 (9) | −0.0015 (10) |
| C9 | 0.0170 (12) | 0.0288 (14) | 0.0279 (14) | 0.0025 (10) | −0.0003 (10) | 0.0004 (11) |
| C10 | 0.0170 (11) | 0.0307 (13) | 0.0233 (13) | 0.0012 (10) | 0.0004 (9) | 0.0023 (10) |
| C1 | 0.0288 (14) | 0.0307 (14) | 0.0318 (15) | −0.0076 (11) | 0.0072 (11) | −0.0024 (12) |
| C12 | 0.0224 (13) | 0.0252 (13) | 0.0300 (14) | 0.0007 (10) | 0.0031 (10) | 0.0038 (11) |
| C13 | 0.0171 (11) | 0.0279 (13) | 0.0263 (13) | 0.0024 (10) | 0.0018 (9) | 0.0036 (10) |
| C11 | 0.0196 (12) | 0.0256 (13) | 0.0227 (13) | −0.0048 (10) | 0.0050 (9) | 0.0003 (10) |
| S1—C1 | 1.691 (3) | C7—C8 | 1.473 (4) |
| S1—C4 | 1.713 (3) | C7—H7A | 0.9300 |
| Cl1—C11 | 1.735 (3) | C8—C9 | 1.398 (4) |
| O1—C5 | 1.224 (3) | C8—C13 | 1.400 (4) |
| C2—C1 | 1.369 (4) | C9—C10 | 1.377 (4) |
| C2—C3 | 1.428 (4) | C9—H9A | 0.9300 |
| C2—H2A | 0.9300 | C10—C11 | 1.393 (4) |
| C3—C4 | 1.397 (4) | C10—H10A | 0.9300 |
| C3—H3A | 0.9300 | C1—H1A | 0.9300 |
| C4—C5 | 1.468 (4) | C12—C11 | 1.385 (4) |
| C5—C6 | 1.474 (4) | C12—C13 | 1.386 (4) |
| C6—C7 | 1.333 (4) | C12—H12A | 0.9300 |
| C6—H6A | 0.9300 | C13—H13A | 0.9300 |
| C1—S1—C4 | 92.14 (14) | C9—C8—C7 | 122.6 (3) |
| C1—C2—C3 | 112.8 (3) | C13—C8—C7 | 119.1 (2) |
| C1—C2—H2A | 123.6 | C10—C9—C8 | 121.3 (3) |
| C3—C2—H2A | 123.6 | C10—C9—H9A | 119.4 |
| C4—C3—C2 | 110.6 (2) | C8—C9—H9A | 119.4 |
| C4—C3—H3A | 124.7 | C9—C10—C11 | 119.0 (2) |
| C2—C3—H3A | 124.7 | C9—C10—H10A | 120.5 |
| C3—C4—C5 | 129.8 (2) | C11—C10—H10A | 120.5 |
| C3—C4—S1 | 111.9 (2) | C2—C1—S1 | 112.5 (2) |
| C5—C4—S1 | 118.2 (2) | C2—C1—H1A | 123.7 |
| O1—C5—C4 | 120.3 (3) | S1—C1—H1A | 123.7 |
| O1—C5—C6 | 122.5 (3) | C11—C12—C13 | 118.9 (3) |
| C4—C5—C6 | 117.2 (2) | C11—C12—H12A | 120.6 |
| C7—C6—C5 | 120.9 (3) | C13—C12—H12A | 120.6 |
| C7—C6—H6A | 119.5 | C12—C13—C8 | 121.2 (2) |
| C5—C6—H6A | 119.5 | C12—C13—H13A | 119.4 |
| C6—C7—C8 | 126.2 (3) | C8—C13—H13A | 119.4 |
| C6—C7—H7A | 116.9 | C12—C11—C10 | 121.3 (2) |
| C8—C7—H7A | 116.9 | C12—C11—Cl1 | 119.3 (2) |
| C9—C8—C13 | 118.3 (3) | C10—C11—Cl1 | 119.3 (2) |
| C1—C2—C3—C4 | 0.0 (4) | C6—C7—C8—C13 | 175.3 (3) |
| C2—C3—C4—C5 | 177.7 (3) | C13—C8—C9—C10 | −2.0 (4) |
| C2—C3—C4—S1 | −0.2 (3) | C7—C8—C9—C10 | 177.5 (3) |
| C1—S1—C4—C3 | 0.2 (2) | C8—C9—C10—C11 | 0.8 (4) |
| C1—S1—C4—C5 | −177.9 (2) | C3—C2—C1—S1 | 0.2 (3) |
| C3—C4—C5—O1 | −180.0 (3) | C4—S1—C1—C2 | −0.2 (3) |
| S1—C4—C5—O1 | −2.3 (4) | C11—C12—C13—C8 | −0.6 (4) |
| C3—C4—C5—C6 | 0.2 (5) | C9—C8—C13—C12 | 1.9 (4) |
| S1—C4—C5—C6 | 177.9 (2) | C7—C8—C13—C12 | −177.6 (3) |
| O1—C5—C6—C7 | 10.0 (5) | C13—C12—C11—C10 | −0.6 (4) |
| C4—C5—C6—C7 | −170.1 (3) | C13—C12—C11—Cl1 | −179.6 (2) |
| C5—C6—C7—C8 | 180.0 (3) | C9—C10—C11—C12 | 0.5 (4) |
| C6—C7—C8—C9 | −4.1 (5) | C9—C10—C11—Cl1 | 179.5 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7A···O1 | 0.93 | 2.50 | 2.825 (4) | 101 |
| C13—H13A···O1i | 0.93 | 2.58 | 3.389 (4) | 145 |
| Symmetry code: (i) −x+2, −y+2, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | C13H9ClOS |
| Mr | 248.71 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 5.7023 (3), 13.3576 (8), 14.7017 (10) |
| β (°) | 96.735 (4) |
| V (Å3) | 1112.09 (12) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.50 |
| Crystal size (mm) | 0.45 × 0.13 × 0.12 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.804, 0.942 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 12436, 3238, 2546 |
| Rint | 0.030 |
| (sin θ/λ)max (Å−1) | 0.706 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.199, 1.08 |
| No. of reflections | 3238 |
| No. of parameters | 145 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.76, −0.49 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7A···O1 | 0.93 | 2.50 | 2.825 (4) | 101 |
| C13—H13A···O1i | 0.93 | 2.58 | 3.389 (4) | 145 |
| Symmetry code: (i) −x+2, −y+2, −z+1. |
Footnotes
‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.
Acknowledgements
HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund (grant No. 305/PFIZIK/613312). SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).
References
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Since some chalcone derivatives have shown to be potential nonlinear optical materials (Agrinskaya et al., 1999), a series of new chalcone derivatives have been prepared in our laboratory (Gu, Ji, Patil & Dharmaprakash, 2008; Gu, Ji, Patil, Dharmaprakash & Wang, 2008; Fun et al., 2008; Patil, Dharmaprakash et al., 2007; Patil, Fun et al., 2007; Patil et al., 2006). As part of the ongoing investigation, the title compound has recently been prepared and its crystal structure is reported here.
In the crystal structure of the title compound, (I), the molecule exhibits an E configuration with respect to the C6═C7 double bond with the C5–C6–C7–C8 torsion angle being 180.0 (3)°. The bond lengths and bond angles in (I) are found to have normal values (Allen et al., 1987). The thienyl (S1/C1—C4) and benzene (C8—C13) rings are essentially planar with the maximum deviation from planarity being -0.001 (2) Å for atom S1 and 0.011 (3) Å for atom C8. The thienyl ring and the benzene ring are slightly twisted from each other with a dihedral angle of 6.38 (8)°.
An intramolecular C—H···O hydrogen bond generates a ring motif S(5) (Bernstein et al., 1995). The intramolecular short S···O contact [2.932 (2) Å] stabilizes the molecular conformation. The crystal packing is consolidated by a weak intermolecular C—H···O interaction. Two π–π interactions with the centroid-to-centroid distances of 3.7899 (16) and 3.7891 (16) Å are observed (symmetry codes: 1 - x, 1/2 + y, 1/2 - z; 1 - x, -1/2 + y, 1/2 - z).