Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051768/at2441sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051768/at2441Isup2.hkl |
CCDC reference: 667430
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.088
- Data-to-parameter ratio = 23.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 7.80 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Achanta et al. (2006); Anuradha et al. (2006); Binder et al. (1985); Daikonya et al. (2004); Gao & Ng (2006); Han et al. (2006); Hsu et al. (2006); Khatib et al. (2005); Kiat et al. (2006); Kim, Choi et al. (2006); Kim, Kim et al. (2006); Sarojini et al. (2007); Wirasathien et al. (2006); Yathirajan et al. (2007); Yathirajan, Ashalatha et al. (2006); Yathirajan, Narayana et al. (2006).
The title compound was prepared by the Claisen-Schmidt condensation of equimolar quantities of 1-(2-thienyl)ethanone (1.26 g, 0.01 mol) and 2,3,5-trichlorobenzaldehyde (2.09 g, 0.01 mol) in ethanol (25 ml), in the presence of sodium hydroxide (8 ml, 10%) (see reaction scheme). The product was recrystallized from ethyl acetate by slow evaporation [m.p.: 378 K]. Analysis for C13H7Cl3OS: Found (Calculated) C 49.10 (49.16), H 2.19 (2.22), S 10.02% (10.10%).
All H atoms were found in a difference map, but geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.95 Å.
Chalcones, 1,3-diphenyl-1-propan-3-one derivatives, have a wide range of biological properties, including anticancer (Achanta et al., 2006; Kim, Choi et al., 2006), antiproliferative (Hsu et al., 2006), anti malarial (Wirasathien et al., 2006), anti inflammatory (Anuradha et al., 2006), anti-allergic (Daikonya et al., 2004) and antagonist (Kim, Kim et al., 2006). Chalcones exhibit inhibitory activity against nitric oxide production (Han et al., 2006), dengue 2 virus NS3 protease (Kiat et al., 2006) and tyrosinase (Khatib et al., 2005). Some chalcone derivatives exhibit nonlinear optical properties (Gao & Ng, 2006). Thiophene analogues of antiviral chalcones have been studied (Binder et al., 1985). The crystal structures of (2E)-1-(3-bromo-2-thienyl)-3-(4-chlorophenyl)prop-2-en-1-one (Yathirajan, Ashalatha et al., 2006), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxy-2,3,6-trimethylphenyl)prop-2-en-1-one (Yathirajan, Narayana et al., 2006), (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007) and (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one(Yathirajan et al., 2007), have been reported. The structure determination of the title compound was undertaken as a part of our study on chalcones and related derivatives.
Geometric parameters of the title compound are in the usual ranges. The molecule is almost planar (r.m.s. deviation of all non-H atoms 0.193 Å). The C–C double bond is trans configured. The bond between the carbonyl bond and the thienyl ring is in an eclipsed conformation. The crystal packing is stabilized by a weak C—H···O hydrogen bond.
For related literature, see: Achanta et al. (2006); Anuradha et al. (2006); Binder et al. (1985); Daikonya et al. (2004); Gao & Ng (2006); Han et al. (2006); Hsu et al. (2006); Khatib et al. (2005); Kiat et al. (2006); Kim, Choi et al. (2006); Kim, Kim et al. (2006); Sarojini et al. (2007); Wirasathien et al. (2006); Yathirajan et al. (2007); Yathirajan, Ashalatha et al. (2006); Yathirajan, Narayana et al. (2006).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. | |
Fig. 2. The formation of the title compound. |
C13H7Cl3OS | F(000) = 640 |
Mr = 317.60 | Dx = 1.594 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21250 reflections |
a = 16.7102 (11) Å | θ = 3.8–29.8° |
b = 7.5130 (4) Å | µ = 0.83 mm−1 |
c = 10.8805 (8) Å | T = 173 K |
β = 104.395 (5)° | Block, colourless |
V = 1323.09 (15) Å3 | 0.31 × 0.25 × 0.19 mm |
Z = 4 |
Stoe IPDSII two-circle diffractometer | 3764 independent reflections |
Radiation source: fine-focus sealed tube | 3276 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 29.8°, θmin = 3.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −23→23 |
Tmin = 0.783, Tmax = 0.858 | k = −10→10 |
20538 measured reflections | l = −15→15 |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.3998P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3764 reflections | Δρmax = 0.37 e Å−3 |
164 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0137 (17) |
C13H7Cl3OS | V = 1323.09 (15) Å3 |
Mr = 317.60 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.7102 (11) Å | µ = 0.83 mm−1 |
b = 7.5130 (4) Å | T = 173 K |
c = 10.8805 (8) Å | 0.31 × 0.25 × 0.19 mm |
β = 104.395 (5)° |
Stoe IPDSII two-circle diffractometer | 3764 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 3276 reflections with I > 2σ(I) |
Tmin = 0.783, Tmax = 0.858 | Rint = 0.037 |
20538 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.37 e Å−3 |
3764 reflections | Δρmin = −0.40 e Å−3 |
164 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. |
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 | ||
Cl1 | 0.87602 (2) | 0.58544 (6) | 0.89280 (3) | 0.03789 (11) | |
Cl2 | 1.01174 (2) | 0.38496 (6) | 0.79526 (4) | 0.04403 (12) | |
Cl3 | 0.81790 (3) | 0.39170 (6) | 0.31918 (4) | 0.04020 (12) | |
S1 | 0.42317 (2) | 0.91675 (6) | 0.66226 (4) | 0.03423 (11) | |
O1 | 0.60078 (7) | 0.86595 (15) | 0.78673 (9) | 0.0314 (2) | |
C1 | 0.71879 (8) | 0.67660 (18) | 0.69127 (12) | 0.0242 (2) | |
H1 | 0.7324 | 0.7170 | 0.7767 | 0.029* | |
C2 | 0.64235 (8) | 0.71009 (19) | 0.62167 (12) | 0.0251 (2) | |
H2 | 0.6267 | 0.6743 | 0.5353 | 0.030* | |
C3 | 0.58164 (8) | 0.80322 (17) | 0.67877 (12) | 0.0231 (2) | |
C4 | 0.49649 (8) | 0.81260 (17) | 0.60132 (12) | 0.0223 (2) | |
C5 | 0.46220 (8) | 0.74799 (18) | 0.47791 (12) | 0.0242 (2) | |
H5 | 0.4923 | 0.6856 | 0.4280 | 0.029* | |
C6 | 0.37602 (9) | 0.7891 (2) | 0.43787 (15) | 0.0338 (3) | |
H6 | 0.3421 | 0.7577 | 0.3570 | 0.041* | |
C7 | 0.34764 (10) | 0.8780 (2) | 0.52797 (16) | 0.0359 (3) | |
H7 | 0.2918 | 0.9143 | 0.5169 | 0.043* | |
C11 | 0.78359 (8) | 0.58274 (17) | 0.64720 (12) | 0.0226 (2) | |
C12 | 0.85862 (8) | 0.53493 (18) | 0.73275 (12) | 0.0253 (2) | |
C13 | 0.91959 (8) | 0.44393 (19) | 0.69000 (14) | 0.0283 (3) | |
C14 | 0.90810 (9) | 0.39832 (19) | 0.56313 (14) | 0.0294 (3) | |
H14 | 0.9496 | 0.3364 | 0.5344 | 0.035* | |
C15 | 0.83386 (8) | 0.44621 (19) | 0.47927 (13) | 0.0264 (3) | |
C16 | 0.77229 (8) | 0.53606 (18) | 0.51859 (12) | 0.0243 (2) | |
H16 | 0.7223 | 0.5663 | 0.4588 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03548 (19) | 0.0486 (2) | 0.02455 (17) | 0.00456 (15) | −0.00205 (13) | −0.00448 (14) |
Cl2 | 0.02560 (18) | 0.0533 (3) | 0.0459 (2) | 0.01070 (15) | −0.00474 (15) | −0.00116 (18) |
Cl3 | 0.0422 (2) | 0.0515 (2) | 0.02833 (18) | 0.01138 (16) | 0.01151 (14) | −0.00645 (15) |
S1 | 0.03290 (19) | 0.0422 (2) | 0.03047 (18) | 0.01007 (14) | 0.01326 (14) | −0.00051 (14) |
O1 | 0.0322 (5) | 0.0395 (6) | 0.0224 (4) | 0.0022 (4) | 0.0068 (4) | −0.0056 (4) |
C1 | 0.0251 (6) | 0.0262 (6) | 0.0214 (5) | 0.0010 (4) | 0.0064 (4) | −0.0001 (4) |
C2 | 0.0248 (6) | 0.0302 (6) | 0.0209 (5) | 0.0021 (5) | 0.0067 (4) | −0.0010 (5) |
C3 | 0.0252 (6) | 0.0243 (6) | 0.0207 (5) | 0.0012 (4) | 0.0075 (4) | 0.0020 (4) |
C4 | 0.0243 (6) | 0.0223 (6) | 0.0223 (5) | 0.0029 (4) | 0.0093 (4) | 0.0019 (4) |
C5 | 0.0206 (5) | 0.0308 (6) | 0.0208 (5) | 0.0025 (4) | 0.0045 (4) | −0.0005 (5) |
C6 | 0.0271 (6) | 0.0386 (8) | 0.0326 (7) | 0.0003 (6) | 0.0018 (5) | −0.0004 (6) |
C7 | 0.0255 (6) | 0.0404 (8) | 0.0427 (8) | 0.0060 (6) | 0.0102 (6) | 0.0078 (6) |
C11 | 0.0212 (5) | 0.0231 (6) | 0.0231 (5) | −0.0008 (4) | 0.0049 (4) | 0.0018 (4) |
C12 | 0.0233 (6) | 0.0264 (6) | 0.0242 (6) | −0.0013 (4) | 0.0024 (5) | 0.0007 (5) |
C13 | 0.0205 (6) | 0.0282 (6) | 0.0337 (7) | 0.0011 (5) | 0.0018 (5) | 0.0018 (5) |
C14 | 0.0237 (6) | 0.0292 (6) | 0.0358 (7) | 0.0026 (5) | 0.0085 (5) | −0.0009 (5) |
C15 | 0.0265 (6) | 0.0277 (6) | 0.0258 (6) | 0.0008 (5) | 0.0079 (5) | −0.0011 (5) |
C16 | 0.0226 (5) | 0.0268 (6) | 0.0232 (5) | 0.0017 (4) | 0.0054 (4) | 0.0015 (5) |
Cl1—C12 | 1.7348 (14) | C5—C6 | 1.4308 (19) |
Cl2—C13 | 1.7327 (14) | C5—H5 | 0.9500 |
Cl3—C15 | 1.7441 (14) | C6—C7 | 1.365 (2) |
S1—C7 | 1.7016 (18) | C6—H6 | 0.9500 |
S1—C4 | 1.7196 (13) | C7—H7 | 0.9500 |
O1—C3 | 1.2318 (16) | C11—C16 | 1.4090 (18) |
C1—C2 | 1.3370 (18) | C11—C12 | 1.4096 (17) |
C1—C11 | 1.4691 (18) | C12—C13 | 1.3990 (19) |
C1—H1 | 0.9500 | C13—C14 | 1.389 (2) |
C2—C3 | 1.4893 (18) | C14—C15 | 1.3921 (19) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.4641 (18) | C15—C16 | 1.3844 (18) |
C4—C5 | 1.4087 (17) | C16—H16 | 0.9500 |
C7—S1—C4 | 92.21 (7) | C6—C7—H7 | 123.7 |
C2—C1—C11 | 125.69 (12) | S1—C7—H7 | 123.7 |
C2—C1—H1 | 117.2 | C16—C11—C12 | 118.04 (12) |
C11—C1—H1 | 117.2 | C16—C11—C1 | 121.06 (11) |
C1—C2—C3 | 120.40 (12) | C12—C11—C1 | 120.90 (12) |
C1—C2—H2 | 119.8 | C13—C12—C11 | 120.44 (12) |
C3—C2—H2 | 119.8 | C13—C12—Cl1 | 119.11 (10) |
O1—C3—C4 | 121.01 (12) | C11—C12—Cl1 | 120.44 (10) |
O1—C3—C2 | 122.36 (12) | C14—C13—C12 | 121.27 (12) |
C4—C3—C2 | 116.60 (11) | C14—C13—Cl2 | 118.33 (11) |
C5—C4—C3 | 129.70 (11) | C12—C13—Cl2 | 120.40 (11) |
C5—C4—S1 | 111.37 (9) | C13—C14—C15 | 117.92 (13) |
C3—C4—S1 | 118.92 (9) | C13—C14—H14 | 121.0 |
C4—C5—C6 | 110.85 (12) | C15—C14—H14 | 121.0 |
C4—C5—H5 | 124.6 | C16—C15—C14 | 122.22 (13) |
C6—C5—H5 | 124.6 | C16—C15—Cl3 | 118.83 (10) |
C7—C6—C5 | 112.95 (13) | C14—C15—Cl3 | 118.95 (11) |
C7—C6—H6 | 123.5 | C15—C16—C11 | 120.12 (12) |
C5—C6—H6 | 123.5 | C15—C16—H16 | 119.9 |
C6—C7—S1 | 112.61 (11) | C11—C16—H16 | 119.9 |
C11—C1—C2—C3 | 178.59 (12) | C16—C11—C12—C13 | 0.05 (19) |
C1—C2—C3—O1 | 6.4 (2) | C1—C11—C12—C13 | 179.34 (12) |
C1—C2—C3—C4 | −171.87 (12) | C16—C11—C12—Cl1 | −179.07 (10) |
O1—C3—C4—C5 | −179.18 (14) | C1—C11—C12—Cl1 | 0.22 (18) |
C2—C3—C4—C5 | −0.9 (2) | C11—C12—C13—C14 | 0.0 (2) |
O1—C3—C4—S1 | 1.18 (18) | Cl1—C12—C13—C14 | 179.10 (11) |
C2—C3—C4—S1 | 179.47 (9) | C11—C12—C13—Cl2 | −179.92 (10) |
C7—S1—C4—C5 | −0.21 (11) | Cl1—C12—C13—Cl2 | −0.79 (17) |
C7—S1—C4—C3 | 179.49 (11) | C12—C13—C14—C15 | 0.1 (2) |
C3—C4—C5—C6 | −179.12 (13) | Cl2—C13—C14—C15 | 179.98 (11) |
S1—C4—C5—C6 | 0.54 (15) | C13—C14—C15—C16 | −0.2 (2) |
C4—C5—C6—C7 | −0.70 (19) | C13—C14—C15—Cl3 | 179.67 (11) |
C5—C6—C7—S1 | 0.55 (19) | C14—C15—C16—C11 | 0.2 (2) |
C4—S1—C7—C6 | −0.19 (13) | Cl3—C15—C16—C11 | −179.66 (10) |
C2—C1—C11—C16 | 7.3 (2) | C12—C11—C16—C15 | −0.13 (19) |
C2—C1—C11—C12 | −171.96 (13) | C1—C11—C16—C15 | −179.42 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1i | 0.95 | 2.45 | 3.3948 (17) | 174 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H7Cl3OS |
Mr | 317.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 16.7102 (11), 7.5130 (4), 10.8805 (8) |
β (°) | 104.395 (5) |
V (Å3) | 1323.09 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.83 |
Crystal size (mm) | 0.31 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.783, 0.858 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20538, 3764, 3276 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.698 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.088, 1.04 |
No. of reflections | 3764 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.40 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1i | 0.95 | 2.45 | 3.3948 (17) | 173.8 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
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Chalcones, 1,3-diphenyl-1-propan-3-one derivatives, have a wide range of biological properties, including anticancer (Achanta et al., 2006; Kim, Choi et al., 2006), antiproliferative (Hsu et al., 2006), anti malarial (Wirasathien et al., 2006), anti inflammatory (Anuradha et al., 2006), anti-allergic (Daikonya et al., 2004) and antagonist (Kim, Kim et al., 2006). Chalcones exhibit inhibitory activity against nitric oxide production (Han et al., 2006), dengue 2 virus NS3 protease (Kiat et al., 2006) and tyrosinase (Khatib et al., 2005). Some chalcone derivatives exhibit nonlinear optical properties (Gao & Ng, 2006). Thiophene analogues of antiviral chalcones have been studied (Binder et al., 1985). The crystal structures of (2E)-1-(3-bromo-2-thienyl)-3-(4-chlorophenyl)prop-2-en-1-one (Yathirajan, Ashalatha et al., 2006), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxy-2,3,6-trimethylphenyl)prop-2-en-1-one (Yathirajan, Narayana et al., 2006), (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007) and (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one(Yathirajan et al., 2007), have been reported. The structure determination of the title compound was undertaken as a part of our study on chalcones and related derivatives.
Geometric parameters of the title compound are in the usual ranges. The molecule is almost planar (r.m.s. deviation of all non-H atoms 0.193 Å). The C–C double bond is trans configured. The bond between the carbonyl bond and the thienyl ring is in an eclipsed conformation. The crystal packing is stabilized by a weak C—H···O hydrogen bond.