organic compounds
(2E)-3-[4-(Benzyloxy)phenyl]-1-(2,6-dichloro-3-fluorophenyl)prop-2-en-1-one
aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
In the title compound, C22H15Cl2FO2, a chalcone derivative featuring a threefold-halogenated aromatic substituent, the conformation about the C=C bond is E. In the crystal C—H⋯F and C—H⋯Cl contacts connect the molecules into undulating sheets parallel to (101). In addition, C—H⋯π interactions are also present.
Related literature
For background to possible applications of et al. (2002); Modzelewska et al. (2006); Svetaz et al. (2004); Sarojini et al. (2006). For related structures, see: Yathirajan et al. (2006); Betz et al. (2012). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
in pharmacy and industry, see: LinExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812046855/nc2298sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812046855/nc2298Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812046855/nc2298Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812046855/nc2298Isup4.cml
To a stirred solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone (1 g, 4.8 mmol) and 4-(benzyloxy)benzaldehyde (1.01 g, 4.8 mmol) in ethanol (10 ml), powdered KOH (0.40 g, 7.2 mmol) was added at 273 K. The reaction mixture was stirred at room temperature for 2 h. After completion of the reaction, the mixture was poured into ice cold water, acidified with HCl (1.5 N) until the pH value was approximately 3. The solid that precipitated was filtered and dried to afford the title compound as off-white solid, yield: 1.8 g (95%). Single crystals suitable for the X-ray diffraction study were grown from a mixture of toluene and acetone (v:v = 1:1) by slow evaporation at room temperature.
Carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic and vinylic carbon atoms, C–H 0.99 Å for methylene groups) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C).Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level). |
C22H15Cl2FO2 | F(000) = 824 |
Mr = 401.24 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Melting point = 369–367 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1977 (2) Å | Cell parameters from 8954 reflections |
b = 21.6887 (4) Å | θ = 2.5–28.3° |
c = 11.6072 (2) Å | µ = 0.36 mm−1 |
β = 124.629 (1)° | T = 200 K |
V = 1905.29 (6) Å3 | Cube, white |
Z = 4 | 0.40 × 0.17 × 0.14 mm |
Bruker APEXII CCD diffractometer | 4712 independent reflections |
Radiation source: fine-focus sealed tube | 3729 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.681, Tmax = 0.746 | k = −20→28 |
17237 measured reflections | l = −15→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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.8279P] where P = (Fo2 + 2Fc2)/3 |
4712 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C22H15Cl2FO2 | V = 1905.29 (6) Å3 |
Mr = 401.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.1977 (2) Å | µ = 0.36 mm−1 |
b = 21.6887 (4) Å | T = 200 K |
c = 11.6072 (2) Å | 0.40 × 0.17 × 0.14 mm |
β = 124.629 (1)° |
Bruker APEXII CCD diffractometer | 4712 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3729 reflections with I > 2σ(I) |
Tmin = 0.681, Tmax = 0.746 | Rint = 0.027 |
17237 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.40 e Å−3 |
4712 reflections | Δρmin = −0.27 e Å−3 |
244 parameters |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.07669 (6) | 0.33062 (2) | 0.86095 (4) | 0.05144 (14) | |
Cl2 | 1.60001 (7) | 0.17443 (2) | 1.21644 (5) | 0.05090 (14) | |
F1 | 1.35724 (19) | 0.38832 (5) | 0.85238 (13) | 0.0634 (3) | |
O1 | 1.20670 (18) | 0.23629 (6) | 1.15009 (13) | 0.0490 (3) | |
O2 | 0.66727 (17) | −0.00811 (5) | 0.41450 (12) | 0.0422 (3) | |
C1 | 1.2218 (2) | 0.22034 (7) | 1.05687 (16) | 0.0338 (3) | |
C2 | 1.1208 (2) | 0.16972 (8) | 0.96163 (17) | 0.0384 (4) | |
H2 | 1.0530 | 0.1445 | 0.9813 | 0.046* | |
C3 | 1.1186 (2) | 0.15692 (7) | 0.84785 (16) | 0.0319 (3) | |
H3 | 1.1970 | 0.1800 | 0.8360 | 0.038* | |
C4 | 0.6360 (2) | −0.00076 (8) | 0.27948 (17) | 0.0397 (4) | |
H4A | 0.7452 | −0.0099 | 0.2848 | 0.048* | |
H4B | 0.6001 | 0.0422 | 0.2465 | 0.048* | |
C11 | 1.3486 (2) | 0.25530 (6) | 1.03696 (14) | 0.0283 (3) | |
C12 | 1.2938 (2) | 0.30701 (7) | 0.95115 (15) | 0.0323 (3) | |
C13 | 1.4134 (3) | 0.33938 (7) | 0.93831 (17) | 0.0394 (4) | |
C14 | 1.5873 (3) | 0.32290 (8) | 1.01107 (18) | 0.0421 (4) | |
H14 | 1.6678 | 0.3463 | 1.0022 | 0.050* | |
C15 | 1.6452 (2) | 0.27204 (8) | 1.09749 (17) | 0.0393 (4) | |
H15 | 1.7658 | 0.2601 | 1.1489 | 0.047* | |
C16 | 1.5253 (2) | 0.23868 (7) | 1.10837 (15) | 0.0316 (3) | |
C21 | 1.0085 (2) | 0.11127 (7) | 0.73997 (16) | 0.0316 (3) | |
C22 | 0.8987 (2) | 0.06930 (8) | 0.74900 (17) | 0.0397 (4) | |
H22 | 0.9000 | 0.0682 | 0.8314 | 0.048* | |
C23 | 0.7894 (3) | 0.02991 (8) | 0.64018 (18) | 0.0423 (4) | |
H23 | 0.7164 | 0.0018 | 0.6482 | 0.051* | |
C24 | 0.7851 (2) | 0.03105 (7) | 0.51816 (16) | 0.0343 (3) | |
C25 | 0.8940 (2) | 0.07133 (7) | 0.50716 (17) | 0.0340 (3) | |
H25 | 0.8936 | 0.0719 | 0.4252 | 0.041* | |
C26 | 1.0036 (2) | 0.11089 (7) | 0.61807 (17) | 0.0338 (3) | |
H26 | 1.0775 | 0.1386 | 0.6102 | 0.041* | |
C31 | 0.4920 (2) | −0.04454 (7) | 0.18024 (16) | 0.0351 (3) | |
C32 | 0.5074 (2) | −0.10705 (8) | 0.21101 (17) | 0.0392 (4) | |
H32 | 0.6079 | −0.1217 | 0.2969 | 0.047* | |
C33 | 0.3791 (3) | −0.14809 (9) | 0.11877 (18) | 0.0459 (4) | |
H33 | 0.3918 | −0.1907 | 0.1414 | 0.055* | |
C34 | 0.2328 (3) | −0.12764 (10) | −0.00587 (19) | 0.0499 (5) | |
H34 | 0.1447 | −0.1561 | −0.0695 | 0.060* | |
C35 | 0.2144 (3) | −0.06611 (11) | −0.03803 (19) | 0.0570 (5) | |
H35 | 0.1131 | −0.0519 | −0.1240 | 0.068* | |
C36 | 0.3439 (3) | −0.02427 (9) | 0.05494 (19) | 0.0489 (4) | |
H36 | 0.3302 | 0.0183 | 0.0321 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0470 (3) | 0.0639 (3) | 0.0343 (2) | 0.0235 (2) | 0.01765 (19) | 0.00794 (19) |
Cl2 | 0.0530 (3) | 0.0481 (3) | 0.0527 (3) | 0.0169 (2) | 0.0307 (2) | 0.0229 (2) |
F1 | 0.0982 (10) | 0.0362 (6) | 0.0626 (7) | 0.0085 (6) | 0.0497 (7) | 0.0160 (5) |
O1 | 0.0587 (8) | 0.0596 (8) | 0.0430 (7) | −0.0113 (7) | 0.0375 (7) | −0.0124 (6) |
O2 | 0.0528 (7) | 0.0349 (6) | 0.0353 (6) | −0.0162 (5) | 0.0228 (6) | −0.0089 (5) |
C1 | 0.0340 (8) | 0.0385 (8) | 0.0293 (7) | −0.0024 (7) | 0.0183 (6) | −0.0012 (6) |
C2 | 0.0388 (9) | 0.0404 (9) | 0.0404 (8) | −0.0120 (7) | 0.0251 (7) | −0.0061 (7) |
C3 | 0.0299 (8) | 0.0297 (7) | 0.0336 (7) | −0.0026 (6) | 0.0166 (6) | −0.0014 (6) |
C4 | 0.0460 (9) | 0.0328 (8) | 0.0352 (8) | −0.0060 (7) | 0.0200 (7) | −0.0020 (7) |
C11 | 0.0337 (8) | 0.0275 (7) | 0.0219 (6) | −0.0026 (6) | 0.0147 (6) | −0.0044 (5) |
C12 | 0.0373 (8) | 0.0321 (7) | 0.0233 (7) | 0.0029 (6) | 0.0147 (6) | −0.0032 (6) |
C13 | 0.0610 (11) | 0.0252 (7) | 0.0335 (8) | −0.0018 (7) | 0.0277 (8) | 0.0006 (6) |
C14 | 0.0498 (10) | 0.0384 (9) | 0.0427 (9) | −0.0165 (8) | 0.0291 (8) | −0.0073 (7) |
C15 | 0.0339 (8) | 0.0436 (9) | 0.0362 (8) | −0.0060 (7) | 0.0174 (7) | −0.0049 (7) |
C16 | 0.0355 (8) | 0.0292 (7) | 0.0271 (7) | 0.0012 (6) | 0.0160 (6) | 0.0017 (6) |
C21 | 0.0304 (7) | 0.0271 (7) | 0.0334 (7) | −0.0014 (6) | 0.0157 (6) | −0.0019 (6) |
C22 | 0.0506 (10) | 0.0338 (8) | 0.0338 (8) | −0.0099 (7) | 0.0235 (8) | −0.0017 (6) |
C23 | 0.0532 (11) | 0.0325 (8) | 0.0405 (9) | −0.0151 (8) | 0.0261 (8) | −0.0026 (7) |
C24 | 0.0385 (9) | 0.0235 (7) | 0.0355 (8) | −0.0037 (6) | 0.0178 (7) | −0.0043 (6) |
C25 | 0.0351 (8) | 0.0325 (8) | 0.0365 (8) | −0.0018 (7) | 0.0216 (7) | −0.0052 (6) |
C26 | 0.0323 (8) | 0.0316 (8) | 0.0401 (8) | −0.0043 (6) | 0.0221 (7) | −0.0051 (6) |
C31 | 0.0375 (8) | 0.0357 (8) | 0.0298 (7) | −0.0025 (7) | 0.0178 (7) | −0.0019 (6) |
C32 | 0.0424 (9) | 0.0380 (9) | 0.0296 (8) | −0.0038 (7) | 0.0160 (7) | 0.0003 (6) |
C33 | 0.0602 (12) | 0.0400 (9) | 0.0399 (9) | −0.0137 (9) | 0.0299 (9) | −0.0075 (7) |
C34 | 0.0494 (11) | 0.0637 (12) | 0.0352 (9) | −0.0186 (10) | 0.0232 (8) | −0.0167 (8) |
C35 | 0.0410 (10) | 0.0772 (15) | 0.0328 (9) | 0.0045 (10) | 0.0091 (8) | −0.0019 (9) |
C36 | 0.0474 (11) | 0.0455 (10) | 0.0409 (9) | 0.0067 (8) | 0.0175 (8) | 0.0052 (8) |
Cl1—C12 | 1.7230 (17) | C15—H15 | 0.9500 |
Cl2—C16 | 1.7344 (15) | C21—C26 | 1.389 (2) |
F1—C13 | 1.3425 (18) | C21—C22 | 1.408 (2) |
O1—C1 | 1.2167 (19) | C22—C23 | 1.376 (2) |
O2—C24 | 1.3643 (18) | C22—H22 | 0.9500 |
O2—C4 | 1.4327 (19) | C23—C24 | 1.395 (2) |
C1—C2 | 1.457 (2) | C23—H23 | 0.9500 |
C1—C11 | 1.515 (2) | C24—C25 | 1.388 (2) |
C2—C3 | 1.338 (2) | C25—C26 | 1.391 (2) |
C2—H2 | 0.9500 | C25—H25 | 0.9500 |
C3—C21 | 1.460 (2) | C26—H26 | 0.9500 |
C3—H3 | 0.9500 | C31—C36 | 1.383 (2) |
C4—C31 | 1.500 (2) | C31—C32 | 1.389 (2) |
C4—H4A | 0.9900 | C32—C33 | 1.377 (2) |
C4—H4B | 0.9900 | C32—H32 | 0.9500 |
C11—C16 | 1.388 (2) | C33—C34 | 1.374 (3) |
C11—C12 | 1.390 (2) | C33—H33 | 0.9500 |
C12—C13 | 1.383 (2) | C34—C35 | 1.370 (3) |
C13—C14 | 1.366 (3) | C34—H34 | 0.9500 |
C14—C15 | 1.378 (2) | C35—C36 | 1.395 (3) |
C14—H14 | 0.9500 | C35—H35 | 0.9500 |
C15—C16 | 1.383 (2) | C36—H36 | 0.9500 |
C24—O2—C4 | 117.41 (12) | C26—C21—C3 | 118.88 (14) |
O1—C1—C2 | 122.91 (15) | C22—C21—C3 | 123.48 (14) |
O1—C1—C11 | 118.69 (14) | C23—C22—C21 | 120.93 (15) |
C2—C1—C11 | 118.39 (13) | C23—C22—H22 | 119.5 |
C3—C2—C1 | 123.41 (15) | C21—C22—H22 | 119.5 |
C3—C2—H2 | 118.3 | C22—C23—C24 | 120.38 (15) |
C1—C2—H2 | 118.3 | C22—C23—H23 | 119.8 |
C2—C3—C21 | 126.97 (15) | C24—C23—H23 | 119.8 |
C2—C3—H3 | 116.5 | O2—C24—C25 | 124.31 (14) |
C21—C3—H3 | 116.5 | O2—C24—C23 | 115.75 (14) |
O2—C4—C31 | 108.06 (13) | C25—C24—C23 | 119.92 (14) |
O2—C4—H4A | 110.1 | C24—C25—C26 | 118.97 (14) |
C31—C4—H4A | 110.1 | C24—C25—H25 | 120.5 |
O2—C4—H4B | 110.1 | C26—C25—H25 | 120.5 |
C31—C4—H4B | 110.1 | C21—C26—C25 | 122.23 (15) |
H4A—C4—H4B | 108.4 | C21—C26—H26 | 118.9 |
C16—C11—C12 | 117.55 (14) | C25—C26—H26 | 118.9 |
C16—C11—C1 | 121.37 (13) | C36—C31—C32 | 118.46 (16) |
C12—C11—C1 | 121.01 (14) | C36—C31—C4 | 121.24 (16) |
C13—C12—C11 | 119.96 (15) | C32—C31—C4 | 120.27 (15) |
C13—C12—Cl1 | 120.13 (12) | C33—C32—C31 | 120.94 (16) |
C11—C12—Cl1 | 119.91 (13) | C33—C32—H32 | 119.5 |
F1—C13—C14 | 119.16 (16) | C31—C32—H32 | 119.5 |
F1—C13—C12 | 119.19 (17) | C34—C33—C32 | 120.26 (18) |
C14—C13—C12 | 121.65 (15) | C34—C33—H33 | 119.9 |
C13—C14—C15 | 119.46 (16) | C32—C33—H33 | 119.9 |
C13—C14—H14 | 120.3 | C35—C34—C33 | 119.79 (17) |
C15—C14—H14 | 120.3 | C35—C34—H34 | 120.1 |
C14—C15—C16 | 119.14 (16) | C33—C34—H34 | 120.1 |
C14—C15—H15 | 120.4 | C34—C35—C36 | 120.27 (18) |
C16—C15—H15 | 120.4 | C34—C35—H35 | 119.9 |
C15—C16—C11 | 122.21 (14) | C36—C35—H35 | 119.9 |
C15—C16—Cl2 | 118.54 (13) | C31—C36—C35 | 120.29 (18) |
C11—C16—Cl2 | 119.25 (12) | C31—C36—H36 | 119.9 |
C26—C21—C22 | 117.55 (14) | C35—C36—H36 | 119.9 |
O1—C1—C2—C3 | 170.87 (17) | C2—C3—C21—C26 | 169.97 (17) |
C11—C1—C2—C3 | −8.0 (2) | C2—C3—C21—C22 | −6.4 (3) |
C1—C2—C3—C21 | −173.56 (16) | C26—C21—C22—C23 | −0.6 (3) |
C24—O2—C4—C31 | −175.17 (14) | C3—C21—C22—C23 | 175.83 (16) |
O1—C1—C11—C16 | 88.4 (2) | C21—C22—C23—C24 | −0.2 (3) |
C2—C1—C11—C16 | −92.69 (18) | C4—O2—C24—C25 | −9.4 (2) |
O1—C1—C11—C12 | −88.61 (19) | C4—O2—C24—C23 | 169.19 (15) |
C2—C1—C11—C12 | 90.29 (18) | C22—C23—C24—O2 | −177.49 (16) |
C16—C11—C12—C13 | 0.7 (2) | C22—C23—C24—C25 | 1.2 (3) |
C1—C11—C12—C13 | 177.82 (13) | O2—C24—C25—C26 | 177.34 (15) |
C16—C11—C12—Cl1 | −179.34 (11) | C23—C24—C25—C26 | −1.2 (2) |
C1—C11—C12—Cl1 | −2.20 (19) | C22—C21—C26—C25 | 0.6 (2) |
C11—C12—C13—F1 | 178.39 (13) | C3—C21—C26—C25 | −176.04 (15) |
Cl1—C12—C13—F1 | −1.6 (2) | C24—C25—C26—C21 | 0.3 (2) |
C11—C12—C13—C14 | −1.7 (2) | O2—C4—C31—C36 | 127.10 (17) |
Cl1—C12—C13—C14 | 178.27 (13) | O2—C4—C31—C32 | −54.7 (2) |
F1—C13—C14—C15 | −178.82 (15) | C36—C31—C32—C33 | 0.4 (3) |
C12—C13—C14—C15 | 1.3 (3) | C4—C31—C32—C33 | −177.76 (16) |
C13—C14—C15—C16 | 0.1 (2) | C31—C32—C33—C34 | −0.1 (3) |
C14—C15—C16—C11 | −1.2 (2) | C32—C33—C34—C35 | −0.3 (3) |
C14—C15—C16—Cl2 | 179.46 (12) | C33—C34—C35—C36 | 0.3 (3) |
C12—C11—C16—C15 | 0.8 (2) | C32—C31—C36—C35 | −0.4 (3) |
C1—C11—C16—C15 | −176.37 (14) | C4—C31—C36—C35 | 177.73 (18) |
C12—C11—C16—Cl2 | −179.88 (11) | C34—C35—C36—C31 | 0.1 (3) |
C1—C11—C16—Cl2 | 2.99 (19) |
Cg is the centroid of the C21–C26 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···F1i | 0.95 | 2.55 | 3.375 (2) | 145 |
C34—H34···Cl1ii | 0.95 | 2.80 | 3.5462 (18) | 136 |
C14—H14···Cgiii | 0.95 | 2.51 | 3.297 (2) | 140 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H15Cl2FO2 |
Mr | 401.24 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 9.1977 (2), 21.6887 (4), 11.6072 (2) |
β (°) | 124.629 (1) |
V (Å3) | 1905.29 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.40 × 0.17 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.681, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17237, 4712, 3729 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.101, 1.02 |
No. of reflections | 4712 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.27 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg is the centroid of the C21–C26 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···F1i | 0.95 | 2.55 | 3.375 (2) | 145.1 |
C34—H34···Cl1ii | 0.95 | 2.80 | 3.5462 (18) | 136.0 |
C14—H14···Cgiii | 0.95 | 2.51 | 3.297 (2) | 140 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1, −y−1/2, z−1/2. |
Acknowledgements
ASP thanks the UOM for research facilities.
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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 α-β-unsaturated ketones containing a reactive Michael system. Some substituted chalcones and their derivatives have been reported to possess interesting biological properties such as antitubercular (Lin et al., 2002), anticancer (Modzelewska et al., 2006) and antifungal (Svetaz et al., 2004) activity. Chalcones also find application as organic nonlinear optical materials for their SHG conversion efficiency (Sarojini et al., 2006). The crystal structures of some chalcones have been reported (Yathirajan et al., 2006; Betz et al., 2012). As part of our ongoing studies on chalcones, the title compound was synthesized.
The C=C bond in the Michael system is (E)-configured. The least-squares planes defined by the respective carbon atoms of the two terminal aromatic moieties intersect at an angle of 48.50 (10) ° and enclose angles of 62.82 (11) ° and 74.58 (8) ° with the least-squares plane defined by the carbon atoms of the central phenyl group. The larger of the latter two angles is created by the halogenated phenyl moiety (Fig 1).
In the crystal, intermolecular C–H···F and C–H···Cl contacts whose range invariably falls by more than 0.1 Å below the sum of van-der-Waals radii of the corresponding atoms are observed. These contacts are exclusively supported by hydrogen atoms on the central as well as the terminal non-halogenated phenyl group and connect the molecules to undulated sheets parallel to [1 0 1]. In addition, C–H···π interactions are present. Details about metrical parameters of these contacts as well as information about their symmetry can be found in Table 1. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the C–H···F as well as the C–H···Cl contacts necessitate a C11(11)C11(17) descriptor on the unary level. The shortest intercentroid distance between two aromatic systems was found at 4.5552 (12) Å and is apparent between the central as well as the halogenated phenyl moiety in neighbouring molecules.