organic compounds
of 3-[4-(1-methylethyl)phenyl]-1-(naphthalen-2-yl)prop-2-en-1-one
aLaboratoire de Chimie Appliqué, et Matériaux Téchnologique, Université Larbi Ben M'Hidi, 04000 Oum El Bouaghi, Algeria, and bLaboratoire des Structures, Propriétés et Interactions InterAtomiques, Université Abbes Laghrour Khenchela, 40000 Khenchela, Algeria
*Correspondence e-mail: messai.amel@yahoo.ca
The title compound, C22H20O, was synthesized by reacting 4-isopropylbenzaldehyde with 2-acetonaphtone by aldolic condensation under Claisen–Schmidt conditions. The molecule consists of a naphthalene group and a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone linker. The naphthalene ring system is almost planar [maximum deviation from the least-squares plane = 0.026 (10) Å] and subtends a dihedral angle of 52.31 (4)° with the benzene ring. The propenone linker, in turn, deviates slightly more from planarity [maximum deviation = 0.125 (18) Å] and has its least-squares plane oriented midway the former two, at 25.62 (6) and 28.02 (5)° from the naphthalene ring system and the benzene ring, respectively. Finally, the isopropyl group presents its CC2 plane almost perpendicular to the benzene ring, at 85.30 (4)°. No significant hydrogen bonding or π–π stacking interactions are found in the crystal structure.
Keywords: crystal structure; chalcones; prop-2-en-1-one; Claisen–Schmidt; aldolic condensation.
CCDC reference: 1017044
1. Related literature
For ); Mabry et al. (1970); Harborne (1988, 1994); Wong (1970). For compilation and discussion of the syntheses of and their analogues, see: Dhar (1981); Lévai (1997).
as important starting materials or intermediates for the synthesis of naturally occurring see: Geissmann (19622. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1017044
10.1107/S1600536814017528/bg2534sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814017528/bg2534Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814017528/bg2534Isup3.cml
A mixture of 2-acetonaphtone (0.01 mole) and 4-isopropyl benzaldehyde (0.01 mole) was stirred in ethanol (50 ml) and then a solution of 15 ml sodium hydroxide (0.04 mole) was added drop wase. The mixture was kept for four h at room temperature and then it was poured into crushed ice and acidified with dil. HCl. The product precipitates out as solid. Then it was filtered. Single yellow crystals of 3-[4-(1-methylethyl)phenyl]-1-(2-naphthalenyl)- 2-Propen-1-one were obtain after crystallized from ethyl acetate with 76% in yield.
H atoms were all located in a difference map, repositioned geometrically and further refined with riding constraints (C—H in the range 0.93–0.98 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom)
Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SIR2004 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. |
C22H20O | F(000) = 640 |
Mr = 300.40 | Dx = 1.225 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 7372 reflections |
a = 5.8326 (2) Å | θ = 4.9–66.8° |
b = 17.8578 (6) Å | µ = 0.56 mm−1 |
c = 15.6469 (5) Å | T = 150 K |
β = 91.136 (3)° | Needle, colorless |
V = 1629.42 (9) Å3 | 0.60 × 0.17 × 0.17 mm |
Z = 4 |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 2871 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 2659 reflections with I > 2s˘I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.4678 pixels mm-1 | θmax = 67.8°, θmin = 3.8° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −21→20 |
Tmin = 0.794, Tmax = 1.000 | l = −18→18 |
12851 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) = 0.097 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3775P] where P = (Fo2 + 2Fc2)/3 |
2871 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C22H20O | V = 1629.42 (9) Å3 |
Mr = 300.40 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 5.8326 (2) Å | µ = 0.56 mm−1 |
b = 17.8578 (6) Å | T = 150 K |
c = 15.6469 (5) Å | 0.60 × 0.17 × 0.17 mm |
β = 91.136 (3)° |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 2871 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 2659 reflections with I > 2s˘I) |
Tmin = 0.794, Tmax = 1.000 | Rint = 0.035 |
12851 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.19 e Å−3 |
2871 reflections | Δρmin = −0.20 e Å−3 |
208 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 | ||
O1 | 1.18162 (14) | 0.47189 (5) | 0.89162 (6) | 0.0419 (2) | |
C2 | 0.97778 (19) | 0.48838 (6) | 0.89245 (7) | 0.0303 (3) | |
C3 | 0.79779 (19) | 0.43015 (6) | 0.89363 (7) | 0.0299 (3) | |
H3A | 0.6454 | 0.4433 | 0.8835 | 0.036* | |
C4 | 0.85268 (19) | 0.35895 (6) | 0.90914 (7) | 0.0288 (3) | |
H4 | 1.0034 | 0.3498 | 0.9266 | 0.035* | |
C5 | 0.70261 (18) | 0.29353 (6) | 0.90177 (7) | 0.0269 (2) | |
C6 | 0.48502 (19) | 0.29638 (6) | 0.86111 (7) | 0.0286 (2) | |
H6 | 0.4267 | 0.3421 | 0.8424 | 0.034* | |
C7 | 0.35703 (19) | 0.23184 (6) | 0.84868 (7) | 0.0293 (3) | |
H7 | 0.2147 | 0.2349 | 0.8211 | 0.035* | |
C8 | 0.43772 (19) | 0.16242 (6) | 0.87684 (7) | 0.0300 (3) | |
C9 | 0.3002 (2) | 0.09158 (7) | 0.85949 (8) | 0.0348 (3) | |
H9 | 0.1649 | 0.1054 | 0.8249 | 0.042* | |
C10 | 0.4352 (3) | 0.03475 (8) | 0.80940 (9) | 0.0503 (4) | |
H10A | 0.4867 | 0.0572 | 0.7575 | 0.075* | |
H10B | 0.3391 | −0.0075 | 0.7959 | 0.075* | |
H10C | 0.5653 | 0.0184 | 0.8430 | 0.075* | |
C11 | 0.2174 (2) | 0.05676 (7) | 0.94176 (9) | 0.0398 (3) | |
H11A | 0.1308 | 0.0930 | 0.9729 | 0.060* | |
H11B | 0.3470 | 0.0408 | 0.9759 | 0.060* | |
H11C | 0.1220 | 0.0144 | 0.9285 | 0.060* | |
C12 | 0.6506 (2) | 0.16017 (6) | 0.92011 (8) | 0.0337 (3) | |
H12 | 0.7051 | 0.1148 | 0.9413 | 0.040* | |
C13 | 0.78131 (19) | 0.22435 (6) | 0.93182 (7) | 0.0312 (3) | |
H13 | 0.9229 | 0.2213 | 0.9600 | 0.037* | |
C14 | 0.90716 (18) | 0.56875 (6) | 0.88921 (7) | 0.0276 (3) | |
C15 | 1.05481 (18) | 0.61962 (6) | 0.85525 (7) | 0.0275 (2) | |
H15 | 1.1945 | 0.6031 | 0.8347 | 0.033* | |
C16 | 1.00104 (18) | 0.69660 (6) | 0.85048 (7) | 0.0271 (2) | |
C17 | 1.1488 (2) | 0.74932 (6) | 0.81351 (7) | 0.0320 (3) | |
H17 | 1.2870 | 0.7334 | 0.7910 | 0.038* | |
C18 | 1.0921 (2) | 0.82339 (7) | 0.81026 (8) | 0.0371 (3) | |
H18 | 1.1918 | 0.8575 | 0.7858 | 0.045* | |
C19 | 0.8844 (2) | 0.84836 (7) | 0.84361 (8) | 0.0392 (3) | |
H19 | 0.8469 | 0.8989 | 0.8411 | 0.047* | |
C20 | 0.7377 (2) | 0.79899 (7) | 0.87967 (8) | 0.0354 (3) | |
H20 | 0.6007 | 0.8162 | 0.9019 | 0.042* | |
C21 | 0.79051 (19) | 0.72157 (6) | 0.88392 (7) | 0.0289 (3) | |
C22 | 0.64154 (19) | 0.66816 (7) | 0.91904 (7) | 0.0312 (3) | |
H22 | 0.5034 | 0.6840 | 0.9416 | 0.037* | |
C23 | 0.69527 (19) | 0.59380 (6) | 0.92065 (7) | 0.0303 (3) | |
H23 | 0.5919 | 0.5595 | 0.9426 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0268 (5) | 0.0322 (5) | 0.0666 (6) | 0.0005 (3) | 0.0017 (4) | 0.0070 (4) |
C2 | 0.0276 (6) | 0.0309 (6) | 0.0323 (6) | −0.0010 (5) | −0.0008 (4) | 0.0019 (5) |
C3 | 0.0257 (6) | 0.0300 (6) | 0.0340 (6) | −0.0014 (4) | −0.0001 (4) | 0.0000 (4) |
C4 | 0.0255 (5) | 0.0315 (6) | 0.0295 (6) | −0.0010 (4) | 0.0004 (4) | −0.0009 (4) |
C5 | 0.0259 (6) | 0.0272 (5) | 0.0276 (5) | −0.0001 (4) | 0.0034 (4) | −0.0007 (4) |
C6 | 0.0281 (6) | 0.0269 (5) | 0.0310 (6) | 0.0024 (4) | 0.0004 (4) | 0.0021 (4) |
C7 | 0.0247 (5) | 0.0327 (6) | 0.0304 (6) | −0.0010 (4) | −0.0016 (4) | 0.0020 (4) |
C8 | 0.0297 (6) | 0.0300 (6) | 0.0304 (6) | −0.0036 (4) | 0.0013 (4) | 0.0023 (4) |
C9 | 0.0347 (6) | 0.0309 (6) | 0.0387 (6) | −0.0067 (5) | −0.0058 (5) | 0.0042 (5) |
C10 | 0.0622 (9) | 0.0414 (7) | 0.0477 (8) | −0.0157 (6) | 0.0102 (7) | −0.0098 (6) |
C11 | 0.0374 (7) | 0.0346 (6) | 0.0476 (7) | −0.0070 (5) | 0.0038 (5) | 0.0040 (5) |
C12 | 0.0325 (6) | 0.0270 (6) | 0.0414 (7) | 0.0000 (5) | −0.0036 (5) | 0.0062 (5) |
C13 | 0.0248 (6) | 0.0322 (6) | 0.0364 (6) | 0.0006 (4) | −0.0031 (4) | 0.0027 (5) |
C14 | 0.0259 (5) | 0.0289 (6) | 0.0281 (5) | −0.0029 (4) | −0.0025 (4) | −0.0001 (4) |
C15 | 0.0235 (5) | 0.0304 (6) | 0.0286 (5) | 0.0000 (4) | −0.0005 (4) | −0.0018 (4) |
C16 | 0.0267 (6) | 0.0287 (6) | 0.0257 (5) | −0.0021 (4) | −0.0032 (4) | −0.0012 (4) |
C17 | 0.0305 (6) | 0.0325 (6) | 0.0328 (6) | −0.0038 (5) | −0.0008 (5) | 0.0008 (5) |
C18 | 0.0422 (7) | 0.0309 (6) | 0.0380 (6) | −0.0081 (5) | −0.0029 (5) | 0.0033 (5) |
C19 | 0.0471 (7) | 0.0260 (6) | 0.0440 (7) | 0.0010 (5) | −0.0070 (6) | −0.0028 (5) |
C20 | 0.0351 (6) | 0.0325 (6) | 0.0383 (6) | 0.0038 (5) | −0.0031 (5) | −0.0078 (5) |
C21 | 0.0287 (6) | 0.0306 (6) | 0.0272 (5) | −0.0002 (4) | −0.0040 (4) | −0.0035 (4) |
C22 | 0.0261 (6) | 0.0374 (6) | 0.0304 (6) | 0.0008 (5) | 0.0024 (4) | −0.0036 (5) |
C23 | 0.0267 (6) | 0.0330 (6) | 0.0311 (6) | −0.0044 (4) | 0.0013 (4) | 0.0010 (5) |
O1—C2 | 1.2252 (14) | C11—H11C | 0.9600 |
C2—C3 | 1.4779 (16) | C12—C13 | 1.3865 (16) |
C2—C14 | 1.4938 (16) | C12—H12 | 0.9300 |
C3—C4 | 1.3323 (16) | C13—H13 | 0.9300 |
C3—H3A | 0.9300 | C14—C15 | 1.3666 (16) |
C4—C5 | 1.4630 (15) | C14—C23 | 1.4119 (16) |
C4—H4 | 0.9300 | C15—C16 | 1.4116 (16) |
C5—C13 | 1.3962 (16) | C15—H15 | 0.9300 |
C5—C6 | 1.4093 (16) | C16—C17 | 1.4085 (16) |
C6—C7 | 1.3848 (16) | C16—C21 | 1.4163 (16) |
C6—H6 | 0.9300 | C17—C18 | 1.3643 (17) |
C7—C8 | 1.3944 (16) | C17—H17 | 0.9300 |
C7—H7 | 0.9300 | C18—C19 | 1.4011 (19) |
C8—C12 | 1.4031 (17) | C18—H18 | 0.9300 |
C8—C9 | 1.5192 (15) | C19—C20 | 1.3592 (18) |
C9—C10 | 1.5126 (19) | C19—H19 | 0.9300 |
C9—C11 | 1.5173 (17) | C20—C21 | 1.4177 (16) |
C9—H9 | 0.9800 | C20—H20 | 0.9300 |
C10—H10A | 0.9600 | C21—C22 | 1.4091 (16) |
C10—H10B | 0.9600 | C22—C23 | 1.3645 (17) |
C10—H10C | 0.9600 | C22—H22 | 0.9300 |
C11—H11A | 0.9600 | C23—H23 | 0.9300 |
C11—H11B | 0.9600 | ||
O1—C2—C3 | 121.38 (10) | H11B—C11—H11C | 109.5 |
O1—C2—C14 | 119.84 (10) | C13—C12—C8 | 121.27 (11) |
C3—C2—C14 | 118.75 (10) | C13—C12—H12 | 119.4 |
C4—C3—C2 | 120.37 (10) | C8—C12—H12 | 119.4 |
C4—C3—H3A | 119.8 | C12—C13—C5 | 120.71 (10) |
C2—C3—H3A | 119.8 | C12—C13—H13 | 119.6 |
C3—C4—C5 | 127.34 (11) | C5—C13—H13 | 119.6 |
C3—C4—H4 | 116.3 | C15—C14—C23 | 119.18 (10) |
C5—C4—H4 | 116.3 | C15—C14—C2 | 118.46 (10) |
C13—C5—C6 | 118.11 (10) | C23—C14—C2 | 122.36 (10) |
C13—C5—C4 | 119.20 (10) | C14—C15—C16 | 121.79 (10) |
C6—C5—C4 | 122.60 (10) | C14—C15—H15 | 119.1 |
C7—C6—C5 | 120.76 (10) | C16—C15—H15 | 119.1 |
C7—C6—H6 | 119.6 | C17—C16—C15 | 122.37 (10) |
C5—C6—H6 | 119.6 | C17—C16—C21 | 118.91 (10) |
C6—C7—C8 | 121.20 (10) | C15—C16—C21 | 118.72 (10) |
C6—C7—H7 | 119.4 | C18—C17—C16 | 120.89 (11) |
C8—C7—H7 | 119.4 | C18—C17—H17 | 119.6 |
C7—C8—C12 | 117.89 (10) | C16—C17—H17 | 119.6 |
C7—C8—C9 | 120.68 (10) | C17—C18—C19 | 120.36 (11) |
C12—C8—C9 | 121.42 (10) | C17—C18—H18 | 119.8 |
C10—C9—C11 | 110.02 (11) | C19—C18—H18 | 119.8 |
C10—C9—C8 | 111.90 (10) | C20—C19—C18 | 120.29 (11) |
C11—C9—C8 | 111.44 (10) | C20—C19—H19 | 119.9 |
C10—C9—H9 | 107.8 | C18—C19—H19 | 119.9 |
C11—C9—H9 | 107.8 | C19—C20—C21 | 120.93 (11) |
C8—C9—H9 | 107.8 | C19—C20—H20 | 119.5 |
C9—C10—H10A | 109.5 | C21—C20—H20 | 119.5 |
C9—C10—H10B | 109.5 | C22—C21—C16 | 118.47 (10) |
H10A—C10—H10B | 109.5 | C22—C21—C20 | 122.91 (11) |
C9—C10—H10C | 109.5 | C16—C21—C20 | 118.62 (10) |
H10A—C10—H10C | 109.5 | C23—C22—C21 | 121.52 (10) |
H10B—C10—H10C | 109.5 | C23—C22—H22 | 119.2 |
C9—C11—H11A | 109.5 | C21—C22—H22 | 119.2 |
C9—C11—H11B | 109.5 | C22—C23—C14 | 120.27 (10) |
H11A—C11—H11B | 109.5 | C22—C23—H23 | 119.9 |
C9—C11—H11C | 109.5 | C14—C23—H23 | 119.9 |
H11A—C11—H11C | 109.5 | ||
O1—C2—C3—C4 | 12.04 (18) | C3—C2—C14—C23 | 25.99 (16) |
C14—C2—C3—C4 | −170.07 (10) | C23—C14—C15—C16 | −0.19 (17) |
C2—C3—C4—C5 | −171.37 (10) | C2—C14—C15—C16 | −179.57 (10) |
C3—C4—C5—C13 | −171.33 (11) | C14—C15—C16—C17 | −178.21 (10) |
C3—C4—C5—C6 | 12.27 (18) | C14—C15—C16—C21 | 1.62 (16) |
C13—C5—C6—C7 | −2.28 (16) | C15—C16—C17—C18 | −179.72 (11) |
C4—C5—C6—C7 | 174.15 (10) | C21—C16—C17—C18 | 0.46 (17) |
C5—C6—C7—C8 | 0.81 (17) | C16—C17—C18—C19 | −0.18 (18) |
C6—C7—C8—C12 | 1.52 (17) | C17—C18—C19—C20 | 0.11 (19) |
C6—C7—C8—C9 | −177.39 (10) | C18—C19—C20—C21 | −0.32 (19) |
C7—C8—C9—C10 | 121.61 (13) | C17—C16—C21—C22 | 178.59 (10) |
C12—C8—C9—C10 | −57.26 (15) | C15—C16—C21—C22 | −1.24 (15) |
C7—C8—C9—C11 | −114.72 (12) | C17—C16—C21—C20 | −0.65 (16) |
C12—C8—C9—C11 | 66.40 (15) | C15—C16—C21—C20 | 179.52 (10) |
C7—C8—C12—C13 | −2.40 (18) | C19—C20—C21—C22 | −178.61 (11) |
C9—C8—C12—C13 | 176.50 (11) | C19—C20—C21—C16 | 0.60 (17) |
C8—C12—C13—C5 | 0.94 (18) | C16—C21—C22—C23 | −0.55 (17) |
C6—C5—C13—C12 | 1.41 (16) | C20—C21—C22—C23 | 178.65 (11) |
C4—C5—C13—C12 | −175.14 (10) | C21—C22—C23—C14 | 2.02 (17) |
O1—C2—C14—C15 | 23.27 (16) | C15—C14—C23—C22 | −1.64 (17) |
C3—C2—C14—C15 | −154.66 (10) | C2—C14—C23—C22 | 177.71 (10) |
O1—C2—C14—C23 | −156.08 (11) |
Experimental details
Crystal data | |
Chemical formula | C22H20O |
Mr | 300.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 5.8326 (2), 17.8578 (6), 15.6469 (5) |
β (°) | 91.136 (3) |
V (Å3) | 1629.42 (9) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.60 × 0.17 × 0.17 |
Data collection | |
Diffractometer | Agilent Xcalibur (Atlas, Gemini ultra) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.794, 1.000 |
No. of measured, independent and observed [I > 2s˘I)] reflections | 12851, 2871, 2659 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.097, 1.04 |
No. of reflections | 2871 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.20 |
Computer programs: CrysAlis PRO (Agilent, 2013), SIR2004 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012).
Acknowledgements
The authors thank le Ministére de l'enseignement supérieur et de la Recherche Scientifique–Algérie for financial support.
References
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Chalcones are versatile and convenient intermediates for the synthesis of a wide variety of heterocyclic compounds. The enone moiety of the molecule is a favourable unit for dipolar cycloaddition with numerous reagents providing heterocyclic compounds of different ring sizes with one or several heteroatoms. Their reactions with dinucleophiles usually result in the formation of polycyclic ring systems which may be the skeleton of important heterocyclic compounds.
Among the chalcones and their analogues are especially important starting materials or intermediates for the synthesis of naturally occurring flavonoids (Geissmann, 1962; Mabry et al.,1970; Harborne, 1988,1994; Wong, 1970) and various nitrogen-containing heterocyclic compounds. For this reason, their syntheses have been compiled and discussed in various accounts (Dhar et al., 1981; Lévai, 1997).
We report here the synthesis and the crystal structure determination of 3-[4-(1-methylethyl)phenyl]-1-(2-naphthalenyl)- 2-Propen-1-one (I). The title compound, C22H20O, was synthesized by reacting 4-isopropyl benzaldehyde with 2-acetonaphtone by aldolic condensation using Claisen-Schmidth conditions. The molecule consist basically of a naphthalene group, a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone linker. The naphthalene and benzene rings are planar (maximum deviations from their L·S. planes: 0.026 (10) and 0.0148 (6) Å, respectively) subtending an angle of 52.31 (4)°. The propenone linker, in turn, deviates slightly more from planarityly (max.dev; 0.125 Å) and has its l.s. plane oriented midway the former two, at 25.62 (6) and 28.02 (5)° from each one, respectively. Finally, the isopropyl group presents its CC2 plane almost perpendicular to the benzene ring, at 85.30 (4)°. No significant hydrogen bonding nor π–π stacking interactions are found in the crystal structure.