Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056656/si2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056656/si2045Isup2.hkl |
CCDC reference: 672944
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.077
- Data-to-parameter ratio = 26.0
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.829 1.000 Tmin(prime) and Tmax expected: 0.819 0.884 RR(prime) = 0.895 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.884 Tmax scaled 0.884 Tmin scaled 0.733
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the uses of chalcones, see: Dhar (1981). For related crystal structures, see: Rabinovich & Shakked (1974); Ravishankar et al. (2005); Schmalle et al. (1990).
4-Chlororobenzaldehyde (2.5 g, 0.02 mol) in ethanol is mixed with 4-methylthio acetophenone (2.80 g, 0.02 mol) in 50 ml e thanol and the mixture was treated with 10 ml of 10% NaOH solution at 283 K and stirred for 8 h. The precipitate obtained was filtered, washed with ethanol and dried. Pale yellow rods of the title compound were grown from toluene by slow evaporation. The yield of the isolated product was 3.5 g (60%)
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.98 Å and Uiso=1.2 to 1.5 times Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown shown as small spheres of arbitrary radius. |
C16H13ClOS | F(000) = 600 |
Mr = 288.78 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Melting point: 444(1) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.515 (1) Å | Cell parameters from 4494 reflections |
b = 14.3026 (9) Å | θ = 4.5–32.6° |
c = 5.7280 (3) Å | µ = 0.42 mm−1 |
β = 91.284 (5)° | T = 200 K |
V = 1352.66 (14) Å3 | Prism, colourless |
Z = 4 | 0.46 × 0.37 × 0.29 mm |
Oxford Diffraction Gemini diffractometer | 4494 independent reflections |
Radiation source: fine-focus sealed tube | 2386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.5° |
ϕ and ω scans | h = −24→22 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −21→21 |
Tmin = 0.829, Tmax = 1.000 | l = −8→7 |
12209 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3 |
4494 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C16H13ClOS | V = 1352.66 (14) Å3 |
Mr = 288.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.515 (1) Å | µ = 0.42 mm−1 |
b = 14.3026 (9) Å | T = 200 K |
c = 5.7280 (3) Å | 0.46 × 0.37 × 0.29 mm |
β = 91.284 (5)° |
Oxford Diffraction Gemini diffractometer | 4494 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2386 reflections with I > 2σ(I) |
Tmin = 0.829, Tmax = 1.000 | Rint = 0.038 |
12209 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.28 e Å−3 |
4494 reflections | Δρmin = −0.23 e Å−3 |
173 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 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 | ||
Cl4 | 0.97354 (2) | 0.13561 (3) | −0.14833 (6) | 0.0456 (1) | |
S4 | 0.18062 (2) | 0.10519 (3) | 0.17298 (6) | 0.0317 (1) | |
O1 | 0.54563 (6) | 0.14122 (7) | 0.71632 (15) | 0.0382 (3) | |
C1 | 0.52954 (8) | 0.13336 (9) | 0.5078 (2) | 0.0266 (4) | |
C2 | 0.59470 (8) | 0.13108 (9) | 0.3341 (2) | 0.0276 (4) | |
C3 | 0.66980 (8) | 0.10839 (9) | 0.3972 (2) | 0.0245 (4) | |
C4 | 0.12122 (9) | 0.15828 (11) | 0.3950 (3) | 0.0417 (5) | |
C11 | 0.74201 (8) | 0.11142 (8) | 0.2543 (2) | 0.0225 (4) | |
C12 | 0.81511 (8) | 0.07634 (9) | 0.3441 (2) | 0.0264 (4) | |
C13 | 0.88615 (8) | 0.08273 (9) | 0.2223 (2) | 0.0293 (4) | |
C14 | 0.88454 (8) | 0.12614 (9) | 0.0085 (2) | 0.0269 (4) | |
C15 | 0.81354 (8) | 0.16220 (9) | −0.0877 (2) | 0.0263 (4) | |
C16 | 0.74260 (8) | 0.15401 (8) | 0.0342 (2) | 0.0246 (4) | |
C21 | 0.44370 (8) | 0.12768 (8) | 0.4239 (2) | 0.0232 (4) | |
C22 | 0.38269 (8) | 0.15922 (8) | 0.5672 (2) | 0.0255 (4) | |
C23 | 0.30208 (8) | 0.15462 (8) | 0.4988 (2) | 0.0264 (4) | |
C24 | 0.28069 (8) | 0.11603 (8) | 0.2817 (2) | 0.0230 (4) | |
C25 | 0.34163 (8) | 0.08362 (9) | 0.1382 (2) | 0.0264 (4) | |
C26 | 0.42171 (8) | 0.09072 (9) | 0.2052 (2) | 0.0274 (4) | |
H2 | 0.58245 | 0.14608 | 0.17562 | 0.0331* | |
H3 | 0.67768 | 0.08772 | 0.55367 | 0.0294* | |
H4A | 0.06385 | 0.15646 | 0.34764 | 0.0626* | |
H4B | 0.12909 | 0.12401 | 0.54194 | 0.0626* | |
H4C | 0.13824 | 0.22339 | 0.41688 | 0.0626* | |
H12 | 0.81606 | 0.04723 | 0.49317 | 0.0317* | |
H13 | 0.93518 | 0.05757 | 0.28528 | 0.0351* | |
H15 | 0.81356 | 0.19222 | −0.23563 | 0.0315* | |
H16 | 0.69352 | 0.17762 | −0.03236 | 0.0296* | |
H22 | 0.39678 | 0.18459 | 0.71588 | 0.0306* | |
H23 | 0.26141 | 0.17753 | 0.59856 | 0.0317* | |
H25 | 0.32756 | 0.05620 | −0.00824 | 0.0316* | |
H26 | 0.46250 | 0.07040 | 0.10248 | 0.0328* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0292 (2) | 0.0657 (3) | 0.0423 (2) | −0.0028 (2) | 0.0115 (2) | 0.0008 (2) |
S4 | 0.0282 (2) | 0.0334 (2) | 0.0331 (2) | −0.0029 (2) | −0.0041 (1) | −0.0008 (2) |
O1 | 0.0310 (6) | 0.0587 (7) | 0.0249 (5) | 0.0038 (5) | −0.0013 (4) | −0.0022 (4) |
C1 | 0.0282 (8) | 0.0263 (7) | 0.0253 (7) | 0.0026 (6) | 0.0019 (5) | 0.0014 (6) |
C2 | 0.0268 (7) | 0.0326 (7) | 0.0235 (7) | −0.0006 (6) | 0.0012 (5) | 0.0019 (6) |
C3 | 0.0275 (7) | 0.0243 (7) | 0.0218 (6) | −0.0005 (6) | 0.0023 (5) | 0.0002 (5) |
C4 | 0.0252 (8) | 0.0474 (9) | 0.0526 (9) | 0.0041 (7) | 0.0014 (6) | −0.0073 (7) |
C11 | 0.0247 (7) | 0.0201 (6) | 0.0225 (6) | −0.0015 (5) | −0.0011 (5) | −0.0026 (5) |
C12 | 0.0296 (7) | 0.0263 (7) | 0.0232 (6) | 0.0014 (6) | −0.0024 (5) | 0.0017 (5) |
C13 | 0.0242 (7) | 0.0339 (8) | 0.0295 (7) | 0.0033 (6) | −0.0031 (5) | −0.0013 (6) |
C14 | 0.0244 (7) | 0.0282 (7) | 0.0282 (7) | −0.0042 (6) | 0.0041 (5) | −0.0060 (6) |
C15 | 0.0316 (8) | 0.0267 (7) | 0.0205 (6) | −0.0014 (6) | 0.0008 (5) | 0.0002 (5) |
C16 | 0.0242 (7) | 0.0262 (7) | 0.0234 (7) | 0.0018 (6) | −0.0023 (5) | −0.0020 (5) |
C21 | 0.0243 (7) | 0.0220 (7) | 0.0235 (6) | 0.0003 (5) | 0.0043 (5) | 0.0020 (5) |
C22 | 0.0287 (7) | 0.0274 (7) | 0.0204 (6) | −0.0009 (6) | 0.0011 (5) | −0.0008 (5) |
C23 | 0.0260 (7) | 0.0275 (7) | 0.0260 (7) | 0.0011 (6) | 0.0060 (5) | −0.0016 (5) |
C24 | 0.0267 (7) | 0.0188 (6) | 0.0236 (6) | −0.0023 (5) | −0.0002 (5) | 0.0035 (5) |
C25 | 0.0316 (8) | 0.0271 (7) | 0.0204 (6) | −0.0031 (6) | 0.0016 (5) | −0.0015 (5) |
C26 | 0.0300 (8) | 0.0279 (7) | 0.0245 (7) | 0.0011 (6) | 0.0085 (5) | −0.0009 (6) |
Cl4—C14 | 1.7450 (13) | C23—C24 | 1.3986 (16) |
S4—C4 | 1.7922 (17) | C24—C25 | 1.3930 (18) |
S4—C24 | 1.7598 (13) | C25—C26 | 1.3726 (19) |
O1—C1 | 1.2230 (14) | C2—H2 | 0.9500 |
C1—C2 | 1.4822 (18) | C3—H3 | 0.9500 |
C1—C21 | 1.4889 (18) | C4—H4A | 0.9800 |
C2—C3 | 1.3244 (19) | C4—H4B | 0.9800 |
C3—C11 | 1.4621 (18) | C4—H4C | 0.9800 |
C11—C12 | 1.3950 (18) | C12—H12 | 0.9500 |
C11—C16 | 1.4004 (16) | C13—H13 | 0.9500 |
C12—C13 | 1.3814 (18) | C15—H15 | 0.9500 |
C13—C14 | 1.3728 (17) | C16—H16 | 0.9500 |
C14—C15 | 1.3841 (18) | C22—H22 | 0.9500 |
C15—C16 | 1.3822 (18) | C23—H23 | 0.9500 |
C21—C22 | 1.3891 (18) | C25—H25 | 0.9500 |
C21—C26 | 1.4001 (17) | C26—H26 | 0.9500 |
C22—C23 | 1.3809 (19) | ||
C4—S4—C24 | 103.66 (7) | C1—C2—H2 | 120.00 |
O1—C1—C2 | 120.83 (12) | C3—C2—H2 | 120.00 |
O1—C1—C21 | 120.31 (11) | C2—C3—H3 | 116.00 |
C2—C1—C21 | 118.85 (10) | C11—C3—H3 | 116.00 |
C1—C2—C3 | 120.78 (11) | S4—C4—H4A | 109.00 |
C2—C3—C11 | 127.63 (11) | S4—C4—H4B | 109.00 |
C3—C11—C12 | 119.53 (11) | S4—C4—H4C | 109.00 |
C3—C11—C16 | 122.62 (11) | H4A—C4—H4B | 109.00 |
C12—C11—C16 | 117.71 (12) | H4A—C4—H4C | 109.00 |
C11—C12—C13 | 121.86 (11) | H4B—C4—H4C | 109.00 |
C12—C13—C14 | 118.74 (12) | C11—C12—H12 | 119.00 |
Cl4—C14—C13 | 119.65 (10) | C13—C12—H12 | 119.00 |
Cl4—C14—C15 | 118.82 (9) | C12—C13—H13 | 121.00 |
C13—C14—C15 | 121.53 (12) | C14—C13—H13 | 121.00 |
C14—C15—C16 | 119.17 (11) | C14—C15—H15 | 120.00 |
C11—C16—C15 | 120.98 (12) | C16—C15—H15 | 120.00 |
C1—C21—C22 | 119.31 (10) | C11—C16—H16 | 120.00 |
C1—C21—C26 | 122.37 (11) | C15—C16—H16 | 119.00 |
C22—C21—C26 | 118.31 (12) | C21—C22—H22 | 119.00 |
C21—C22—C23 | 121.62 (11) | C23—C22—H22 | 119.00 |
C22—C23—C24 | 119.59 (11) | C22—C23—H23 | 120.00 |
S4—C24—C23 | 124.46 (10) | C24—C23—H23 | 120.00 |
S4—C24—C25 | 116.56 (9) | C24—C25—H25 | 120.00 |
C23—C24—C25 | 118.98 (12) | C26—C25—H25 | 120.00 |
C24—C25—C26 | 120.98 (11) | C21—C26—H26 | 120.00 |
C21—C26—C25 | 120.47 (12) | C25—C26—H26 | 120.00 |
C4—S4—C24—C23 | 2.51 (12) | C12—C13—C14—C15 | −0.84 (19) |
C4—S4—C24—C25 | −177.35 (10) | C12—C13—C14—Cl4 | 179.71 (10) |
O1—C1—C2—C3 | 21.2 (2) | Cl4—C14—C15—C16 | 179.25 (10) |
O1—C1—C21—C26 | −159.89 (12) | C13—C14—C15—C16 | −0.20 (19) |
C21—C1—C2—C3 | −159.94 (12) | C14—C15—C16—C11 | 1.15 (18) |
O1—C1—C21—C22 | 19.52 (18) | C1—C21—C26—C25 | 177.59 (12) |
C2—C1—C21—C26 | 21.23 (18) | C22—C21—C26—C25 | −1.83 (18) |
C2—C1—C21—C22 | −159.36 (11) | C1—C21—C22—C23 | −179.31 (11) |
C1—C2—C3—C11 | −173.63 (12) | C26—C21—C22—C23 | 0.13 (18) |
C2—C3—C11—C12 | −173.92 (13) | C21—C22—C23—C24 | 1.01 (17) |
C2—C3—C11—C16 | 10.4 (2) | C22—C23—C24—C25 | −0.47 (17) |
C16—C11—C12—C13 | −0.07 (18) | C22—C23—C24—S4 | 179.67 (9) |
C3—C11—C12—C13 | −175.92 (12) | S4—C24—C25—C26 | 178.65 (10) |
C12—C11—C16—C15 | −1.01 (17) | C23—C24—C25—C26 | −1.23 (18) |
C3—C11—C16—C15 | 174.71 (12) | C24—C25—C26—C21 | 2.40 (19) |
C11—C12—C13—C14 | 0.98 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cgi | 0.95 | 2.81 | 3.527 (1) | 133 |
C22—H22···Cgii | 0.95 | 2.94 | 3.550 (1) | 124 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClOS |
Mr | 288.78 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 16.515 (1), 14.3026 (9), 5.7280 (3) |
β (°) | 91.284 (5) |
V (Å3) | 1352.66 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.46 × 0.37 × 0.29 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.829, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12209, 4494, 2386 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.077, 0.86 |
No. of reflections | 4494 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.23 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cgi | 0.95 | 2.81 | 3.527 (1) | 133 |
C22—H22···Cgii | 0.95 | 2.94 | 3.550 (1) | 124 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
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Many patents have appeared in literature describing the usefulness of Chalcones and their derivatives. Their diverse applications such as artificial sweeteners, stabilizers against heat and visible light, color photography, scintillators, polymerization catalysts, fluorescent lightning agents and as brightening agents are well studied and documented (Dhar, 1981). The title material is used as an intermediate to prepare the corresponding pyrazole derivatives which have shown better antiinflamatory and analgesic activities. In the title molecule, C16H13ClOS, Fig.1, the dihedral angle between the two phenyl rings is 51.0 (1)°. The presence of a methylsulfanylphenyl group in the title molecule causes the 4-chlorophenyl group to twist away from each other. There are no classical hydrogen bonds found in the structure. In similar structures like 4,4'-Dimethylchalcone (Rabinovich & Shakked, 1974), 2',6'-Dihydroxy-4,4'-dimethoxychalcone (Schmalle et al., 1990) and 1-(4-Chlorophenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one(Ravishankar et al., 2005), the dihedral angle between the two phenyl rings are 48.6°, 13.1 (4)° and 26.1 (1)° respectively.