organic compounds
(E)-3-(2,3-Dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one
aInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, cDepartment of Physics, Acharya Institute of Technology, Visvesvaraya Technological University, Bangalore 560 107, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and eDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
*Correspondence e-mail: khalil.i@najah.edu
In the title chalcone derivative, C15H9Cl2FO, the dihedral angle between the aromatic rings is 19.13 (15)° and the double bond adopts an E conformation. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds, forming a chain propagating along the [001] direction.
Keywords: crystal structure; chalcone derivative; prop-2-en-1-one; hydrogen bonding.
CCDC reference: 1515842
Structure description
α, β-unsaturated carbonyl function. The classical route for the synthesis of involves the Claisen–Schmidt condensation of an aromatic aldehyde and an aromatic ketone in the presence of aqueous alkaline bases (Jadav et al., 2015). As part of our studies in this area, we herein report the synthesis and of the title compound (Fig. 1).
are compounds that contain anThe dihedral angle between the fluorophenyl and the dichlorophenyl rings is 19.35 (15)°. The trans conformation of the C7=C8 double bond in the central enone group is confirmed by the C7—C8=C9—C10 torsion angle value of −177.3 (2)°. The major twist in the molecule occurs about the C1—C7 bond, as indicated by the C2—C1—C7—C8 torsion angle of −18.5 (4)°.
In the crystal, the molecules are connected via weak C—H⋯O hydrogen bonds (Table 1), forming a C(7) chain propagating along the [001] direction (Fig. 2).
Synthesis and crystallization
A mixture of 2,3-dichlorobenzaldehyde (0.05 mmol), 1-(4-fluorophenyl)ethanone (0.05 mmol) and sodium hydroxide (0.05 mmol) in 80% ethyl alcohol (25 ml) was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was poured in to ice-cold water and kept in the refrigerator for 18 h. The solid formed was filtered, and washed with cold acetic acid (5%). It was then recrystallized from dichloromethane solution (with 3–4 drops of acetonitrile added) to get the title compound in the form of green blocks, m.p. 105°C.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1515842
https://doi.org/10.1107/S2414314616018009/hb4096sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018009/hb4096Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616018009/hb4096Isup3.cml
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).C15H9Cl2FO | F(000) = 600 |
Mr = 295.12 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 1881 reflections |
a = 15.662 (2) Å | θ = 6.2–64.2° |
b = 8.1130 (14) Å | µ = 4.40 mm−1 |
c = 10.9108 (18) Å | T = 296 K |
β = 106.288 (6)° | Block, green |
V = 1330.8 (4) Å3 | 0.28 × 0.26 × 0.25 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2163 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 1881 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.053 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.2°, θmin = 6.2° |
φ and ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −9→9 |
Tmin = 0.372, Tmax = 0.406 | l = −11→12 |
9531 measured reflections |
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)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.210 | w = 1/[σ2(Fo2) + (0.1575P)2 + 0.2475P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2163 reflections | Δρmax = 0.51 e Å−3 |
173 parameters | Δρmin = −0.52 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (3) |
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 esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 | −0.02367 (6) | 0.65394 (16) | 0.20294 (10) | 0.0936 (5) | |
Cl2 | 0.12132 (5) | 0.46410 (11) | 0.11655 (7) | 0.0673 (4) | |
F1 | 0.76924 (12) | 0.0730 (3) | 0.6363 (2) | 0.0855 (8) | |
O1 | 0.40095 (14) | 0.1717 (3) | 0.2333 (2) | 0.0638 (8) | |
C1 | 0.21279 (17) | 0.4408 (3) | 0.3681 (3) | 0.0466 (9) | |
C2 | 0.2207 (2) | 0.4739 (5) | 0.4950 (3) | 0.0633 (11) | |
C3 | 0.1557 (2) | 0.5621 (5) | 0.5317 (4) | 0.0747 (14) | |
C4 | 0.0817 (2) | 0.6185 (4) | 0.4421 (4) | 0.0676 (11) | |
C5 | 0.07215 (18) | 0.5874 (4) | 0.3154 (3) | 0.0568 (10) | |
C6 | 0.13620 (16) | 0.4998 (3) | 0.2767 (3) | 0.0471 (8) | |
C7 | 0.27948 (17) | 0.3469 (3) | 0.3273 (3) | 0.0476 (9) | |
C8 | 0.36255 (17) | 0.3194 (3) | 0.3957 (3) | 0.0496 (9) | |
C9 | 0.42414 (17) | 0.2226 (3) | 0.3428 (3) | 0.0458 (8) | |
C10 | 0.51619 (16) | 0.1877 (3) | 0.4247 (3) | 0.0433 (8) | |
C11 | 0.56881 (19) | 0.0816 (4) | 0.3774 (3) | 0.0549 (10) | |
C12 | 0.6542 (2) | 0.0431 (4) | 0.4488 (4) | 0.0628 (11) | |
C13 | 0.68611 (17) | 0.1113 (4) | 0.5673 (3) | 0.0577 (10) | |
C14 | 0.6357 (2) | 0.2145 (4) | 0.6183 (3) | 0.0646 (11) | |
C15 | 0.55032 (18) | 0.2513 (4) | 0.5467 (3) | 0.0563 (10) | |
H2 | 0.27050 | 0.43640 | 0.55720 | 0.0760* | |
H3 | 0.16260 | 0.58280 | 0.61780 | 0.0890* | |
H4 | 0.03840 | 0.67750 | 0.46680 | 0.0810* | |
H7 | 0.26200 | 0.30220 | 0.24560 | 0.0570* | |
H8 | 0.38250 | 0.36150 | 0.47810 | 0.0590* | |
H11 | 0.54630 | 0.03580 | 0.29660 | 0.0660* | |
H12 | 0.68930 | −0.02790 | 0.41670 | 0.0750* | |
H14 | 0.65870 | 0.25870 | 0.69960 | 0.0770* | |
H15 | 0.51510 | 0.31980 | 0.58070 | 0.0680* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0664 (6) | 0.1289 (10) | 0.0747 (8) | 0.0475 (5) | 0.0020 (5) | −0.0026 (5) |
Cl2 | 0.0556 (6) | 0.0992 (7) | 0.0429 (6) | 0.0174 (3) | 0.0071 (4) | 0.0060 (4) |
F1 | 0.0460 (10) | 0.1197 (17) | 0.0812 (16) | 0.0191 (10) | 0.0020 (9) | 0.0054 (12) |
O1 | 0.0558 (12) | 0.0856 (14) | 0.0449 (13) | 0.0090 (10) | 0.0059 (10) | −0.0047 (11) |
C1 | 0.0388 (13) | 0.0550 (14) | 0.0430 (17) | −0.0003 (10) | 0.0066 (11) | 0.0061 (11) |
C2 | 0.0520 (16) | 0.088 (2) | 0.0457 (19) | 0.0077 (14) | 0.0069 (14) | 0.0009 (15) |
C3 | 0.067 (2) | 0.107 (3) | 0.049 (2) | 0.0118 (18) | 0.0146 (16) | −0.0114 (18) |
C4 | 0.0566 (18) | 0.080 (2) | 0.067 (2) | 0.0125 (15) | 0.0187 (16) | −0.0123 (17) |
C5 | 0.0472 (15) | 0.0613 (15) | 0.058 (2) | 0.0083 (12) | 0.0085 (13) | −0.0003 (14) |
C6 | 0.0390 (13) | 0.0522 (13) | 0.0474 (17) | −0.0013 (11) | 0.0076 (11) | 0.0049 (12) |
C7 | 0.0438 (14) | 0.0530 (14) | 0.0447 (17) | 0.0030 (10) | 0.0103 (11) | 0.0074 (12) |
C8 | 0.0431 (14) | 0.0542 (15) | 0.0484 (17) | 0.0028 (11) | 0.0080 (11) | 0.0015 (12) |
C9 | 0.0435 (13) | 0.0475 (13) | 0.0440 (17) | 0.0008 (10) | 0.0085 (11) | 0.0049 (11) |
C10 | 0.0406 (13) | 0.0456 (12) | 0.0431 (16) | 0.0005 (10) | 0.0106 (11) | 0.0066 (11) |
C11 | 0.0546 (16) | 0.0687 (17) | 0.0415 (18) | 0.0126 (13) | 0.0135 (13) | 0.0034 (13) |
C12 | 0.0542 (16) | 0.076 (2) | 0.061 (2) | 0.0201 (14) | 0.0206 (15) | 0.0078 (15) |
C13 | 0.0384 (14) | 0.0694 (17) | 0.062 (2) | 0.0054 (12) | 0.0086 (13) | 0.0101 (15) |
C14 | 0.0502 (15) | 0.077 (2) | 0.058 (2) | 0.0015 (14) | 0.0010 (14) | −0.0128 (15) |
C15 | 0.0449 (15) | 0.0621 (16) | 0.059 (2) | 0.0049 (12) | 0.0100 (13) | −0.0106 (14) |
Cl1—C5 | 1.737 (3) | C10—C15 | 1.387 (4) |
Cl2—C6 | 1.721 (3) | C11—C12 | 1.382 (5) |
F1—C13 | 1.345 (4) | C12—C13 | 1.366 (5) |
O1—C9 | 1.219 (4) | C13—C14 | 1.371 (4) |
C1—C2 | 1.381 (4) | C14—C15 | 1.379 (4) |
C1—C6 | 1.411 (4) | C2—H2 | 0.9300 |
C1—C7 | 1.460 (4) | C3—H3 | 0.9300 |
C2—C3 | 1.392 (5) | C4—H4 | 0.9300 |
C3—C4 | 1.369 (5) | C7—H7 | 0.9300 |
C4—C5 | 1.372 (5) | C8—H8 | 0.9300 |
C5—C6 | 1.388 (4) | C11—H11 | 0.9300 |
C7—C8 | 1.325 (4) | C12—H12 | 0.9300 |
C8—C9 | 1.481 (4) | C14—H14 | 0.9300 |
C9—C10 | 1.495 (4) | C15—H15 | 0.9300 |
C10—C11 | 1.388 (4) | ||
C2—C1—C6 | 117.5 (3) | F1—C13—C14 | 119.4 (3) |
C2—C1—C7 | 122.4 (3) | C12—C13—C14 | 122.2 (3) |
C6—C1—C7 | 120.1 (3) | C13—C14—C15 | 118.7 (3) |
C1—C2—C3 | 121.4 (3) | C10—C15—C14 | 121.0 (3) |
C2—C3—C4 | 120.5 (4) | C1—C2—H2 | 119.00 |
C3—C4—C5 | 119.3 (3) | C3—C2—H2 | 119.00 |
Cl1—C5—C4 | 118.9 (2) | C2—C3—H3 | 120.00 |
Cl1—C5—C6 | 119.9 (2) | C4—C3—H3 | 120.00 |
C4—C5—C6 | 121.1 (3) | C3—C4—H4 | 120.00 |
Cl2—C6—C1 | 120.4 (2) | C5—C4—H4 | 120.00 |
Cl2—C6—C5 | 119.4 (2) | C1—C7—H7 | 117.00 |
C1—C6—C5 | 120.2 (3) | C8—C7—H7 | 117.00 |
C1—C7—C8 | 126.2 (3) | C7—C8—H8 | 120.00 |
C7—C8—C9 | 120.9 (3) | C9—C8—H8 | 120.00 |
O1—C9—C8 | 120.9 (3) | C10—C11—H11 | 120.00 |
O1—C9—C10 | 119.6 (3) | C12—C11—H11 | 120.00 |
C8—C9—C10 | 119.5 (3) | C11—C12—H12 | 121.00 |
C9—C10—C11 | 118.0 (3) | C13—C12—H12 | 121.00 |
C9—C10—C15 | 123.4 (2) | C13—C14—H14 | 121.00 |
C11—C10—C15 | 118.6 (3) | C15—C14—H14 | 121.00 |
C10—C11—C12 | 120.8 (3) | C10—C15—H15 | 120.00 |
C11—C12—C13 | 118.8 (3) | C14—C15—H15 | 120.00 |
F1—C13—C12 | 118.4 (3) | ||
C6—C1—C2—C3 | 0.0 (5) | C7—C8—C9—O1 | 3.0 (4) |
C7—C1—C2—C3 | −179.2 (3) | C7—C8—C9—C10 | −177.3 (2) |
C2—C1—C6—Cl2 | 179.9 (2) | O1—C9—C10—C11 | −7.4 (4) |
C2—C1—C6—C5 | −0.1 (4) | O1—C9—C10—C15 | 174.9 (3) |
C7—C1—C6—Cl2 | −0.8 (3) | C8—C9—C10—C11 | 173.0 (3) |
C7—C1—C6—C5 | 179.2 (3) | C8—C9—C10—C15 | −4.8 (4) |
C2—C1—C7—C8 | −18.5 (4) | C9—C10—C11—C12 | −179.4 (3) |
C6—C1—C7—C8 | 162.3 (3) | C15—C10—C11—C12 | −1.6 (5) |
C1—C2—C3—C4 | 0.1 (6) | C9—C10—C15—C14 | 179.8 (3) |
C2—C3—C4—C5 | −0.1 (5) | C11—C10—C15—C14 | 2.1 (4) |
C3—C4—C5—Cl1 | 178.0 (3) | C10—C11—C12—C13 | 0.1 (5) |
C3—C4—C5—C6 | 0.0 (5) | C11—C12—C13—F1 | 179.9 (3) |
Cl1—C5—C6—Cl2 | 2.1 (3) | C11—C12—C13—C14 | 1.0 (5) |
Cl1—C5—C6—C1 | −177.9 (2) | F1—C13—C14—C15 | −179.4 (3) |
C4—C5—C6—Cl2 | −179.9 (3) | C12—C13—C14—C15 | −0.6 (5) |
C4—C5—C6—C1 | 0.1 (4) | C13—C14—C15—C10 | −1.0 (5) |
C1—C7—C8—C9 | −179.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.54 | 3.465 (4) | 177 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.
References
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jadav, S. S., Kaptein, S., Timiri, A. K., De Burghgraeve, T., Badavath, V. N., Ganesan, R., Sinha, B. N., Neyts, J., Leyssen, P. & Jayaprakash, V. (2015). Bioorg. Med. Chem. Lett. 25, 1747–1752. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.