organic compounds
E)-3-(2,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
of (aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr
In the title compound, C21H18O4, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 6.60 (2)°. The methoxy groups on the benzene ring are essentially coplanar with the ring; the C—C—O—C torsion angles being 1.6 (2) and −177.1 (1)°. The hydroxy group attached to the naphthalene ring is involved in an intramolecular O—H⋯O hydrogen bond. The relative conformation of the two double bonds in the enone group is s-cisoid. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains propagating along [010].
Keywords: crystal structure; chalcone; enone; benzochalcone; naphthalene.
CCDC reference: 1019819
1. Related literature
For the synthesis and biological properties of chalcone derivatives, see: Fuchigami et al. (2014); Kim et al. (2014); Mai et al. (2014); Smit & D′Na (2014). For details concerning benzochalcone derivatives, see: Juvale et al. (2013); Shin et al. (2013). For related structures, see: Ahn et al. (2013); Lim & Koh (2013).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 1019819
10.1107/S1600536814018704/su2770sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018704/su2770Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018704/su2770Isup3.cml
To a solution of 2,4-dimethoxybenzaldehyde (830 mg, 5 mmol) in 50 ml of ethanol was added 1-hydroxy-2-acetonaphthone (930 mg, 1 mmol) and the temperature was adjusted to around 275–276 K in an ice-bath. To the cooled reaction mixture 5 ml of 50% aqueous KOH solution was added, and the reaction mixture was stirred at room temperature for 24 h. This mixture was poured into iced water (100 ml) and was acidified (pH = 3) with 6 N HCl solution to give a precipitate. Filtration and washing with water afforded the crude solid of the title compound (520 mg, 31%). Recrystallization of the solid from ethanol gave single crystals crystals which were suitable for X-ray diffraction (M.p. 434–435 K).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C21H18O4 | F(000) = 1408 |
Mr = 334.35 | Dx = 1.370 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -C 2yc | Cell parameters from 4341 reflections |
a = 14.1148 (9) Å | θ = 4.3–66.4° |
b = 14.7489 (9) Å | µ = 0.77 mm−1 |
c = 15.5929 (10) Å | T = 147 K |
β = 92.804 (4)° | Needle, orange |
V = 3242.2 (4) Å3 | 0.19 × 0.12 × 0.08 mm |
Z = 8 |
Bruker Kappa APEX DUO CCD diffractometer | 2755 independent reflections |
Radiation source: Bruker ImuS | 2505 reflections with I > 2σ(I) |
Multi-layer optics monochromator | Rint = 0.026 |
ϕ and ω scans | θmax = 66.5°, θmin = 4.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −16→16 |
Tmin = 0.669, Tmax = 0.753 | k = −17→17 |
8800 measured reflections | l = −13→18 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.049P)2 + 1.958P] where P = (Fo2 + 2Fc2)/3 |
2755 reflections | (Δ/σ)max = 0.001 |
232 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C21H18O4 | V = 3242.2 (4) Å3 |
Mr = 334.35 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 14.1148 (9) Å | µ = 0.77 mm−1 |
b = 14.7489 (9) Å | T = 147 K |
c = 15.5929 (10) Å | 0.19 × 0.12 × 0.08 mm |
β = 92.804 (4)° |
Bruker Kappa APEX DUO CCD diffractometer | 2755 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2505 reflections with I > 2σ(I) |
Tmin = 0.669, Tmax = 0.753 | Rint = 0.026 |
8800 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.15 e Å−3 |
2755 reflections | Δρmin = −0.27 e Å−3 |
232 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 | 0.46036 (6) | 0.17828 (6) | 1.03233 (6) | 0.0275 (2) | |
O2 | 0.19523 (6) | 0.11183 (7) | 0.85783 (7) | 0.0345 (3) | |
O3 | 0.17234 (6) | −0.10692 (6) | 0.63594 (6) | 0.0266 (2) | |
O4 | 0.59612 (6) | 0.24290 (6) | 1.12130 (6) | 0.0251 (2) | |
C1 | 0.51556 (9) | 0.13224 (8) | 0.98872 (8) | 0.0210 (3) | |
C2 | 0.47622 (9) | 0.07880 (8) | 0.91593 (8) | 0.0223 (3) | |
H2A | 0.5173 | 0.0432 | 0.8832 | 0.027* | |
C3 | 0.38286 (9) | 0.07983 (8) | 0.89525 (8) | 0.0213 (3) | |
H3A | 0.3454 | 0.1177 | 0.9294 | 0.026* | |
C4 | 0.33198 (8) | 0.03012 (8) | 0.82693 (8) | 0.0201 (3) | |
C5 | 0.23466 (9) | 0.04712 (8) | 0.80855 (8) | 0.0226 (3) | |
C6 | 0.18419 (9) | 0.00040 (9) | 0.74439 (8) | 0.0240 (3) | |
H6A | 0.1190 | 0.0134 | 0.7324 | 0.029* | |
C7 | 0.22926 (9) | −0.06572 (9) | 0.69744 (8) | 0.0215 (3) | |
C8 | 0.32474 (9) | −0.08523 (9) | 0.71418 (8) | 0.0233 (3) | |
H8A | 0.3557 | −0.1302 | 0.6822 | 0.028* | |
C9 | 0.37358 (9) | −0.03735 (9) | 0.77878 (8) | 0.0222 (3) | |
H9A | 0.4386 | −0.0512 | 0.7908 | 0.027* | |
C10 | 0.09670 (11) | 0.13031 (13) | 0.84355 (13) | 0.0516 (5) | |
H10A | 0.0772 | 0.1763 | 0.8845 | 0.077* | |
H10B | 0.0603 | 0.0746 | 0.8514 | 0.077* | |
H10C | 0.0847 | 0.1528 | 0.7849 | 0.077* | |
C11 | 0.21279 (10) | −0.17857 (10) | 0.58794 (9) | 0.0339 (3) | |
H11A | 0.1648 | −0.2029 | 0.5466 | 0.051* | |
H11B | 0.2349 | −0.2269 | 0.6272 | 0.051* | |
H11C | 0.2665 | −0.1551 | 0.5571 | 0.051* | |
C12 | 0.61749 (8) | 0.13277 (8) | 1.01100 (8) | 0.0193 (3) | |
C13 | 0.65294 (8) | 0.18928 (8) | 1.07709 (7) | 0.0190 (3) | |
C14 | 0.75210 (8) | 0.19224 (8) | 1.10073 (7) | 0.0193 (3) | |
C15 | 0.78867 (9) | 0.25063 (8) | 1.16617 (8) | 0.0220 (3) | |
H15A | 0.7470 | 0.2893 | 1.1952 | 0.026* | |
C16 | 0.88385 (9) | 0.25175 (9) | 1.18786 (8) | 0.0251 (3) | |
H16A | 0.9081 | 0.2916 | 1.2315 | 0.030* | |
C17 | 0.94584 (9) | 0.19415 (9) | 1.14567 (8) | 0.0259 (3) | |
H17A | 1.0117 | 0.1946 | 1.1616 | 0.031* | |
C18 | 0.91205 (9) | 0.13741 (9) | 1.08185 (8) | 0.0246 (3) | |
H18A | 0.9549 | 0.0991 | 1.0537 | 0.030* | |
C19 | 0.81422 (9) | 0.13491 (8) | 1.05720 (8) | 0.0203 (3) | |
C20 | 0.77706 (9) | 0.07710 (9) | 0.99071 (8) | 0.0228 (3) | |
H20A | 0.8185 | 0.0382 | 0.9617 | 0.027* | |
C21 | 0.68288 (9) | 0.07699 (8) | 0.96827 (8) | 0.0216 (3) | |
H21A | 0.6599 | 0.0387 | 0.9229 | 0.026* | |
H4O | 0.5337 (15) | 0.2284 (14) | 1.0965 (13) | 0.059 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0193 (4) | 0.0320 (5) | 0.0312 (5) | 0.0025 (4) | −0.0004 (4) | −0.0075 (4) |
O2 | 0.0217 (5) | 0.0350 (6) | 0.0455 (6) | 0.0096 (4) | −0.0106 (4) | −0.0179 (5) |
O3 | 0.0286 (5) | 0.0265 (5) | 0.0242 (5) | −0.0033 (4) | −0.0046 (4) | −0.0038 (4) |
O4 | 0.0202 (5) | 0.0282 (5) | 0.0267 (5) | 0.0035 (4) | −0.0002 (4) | −0.0078 (4) |
C1 | 0.0217 (6) | 0.0192 (6) | 0.0221 (6) | −0.0003 (5) | 0.0010 (5) | 0.0028 (5) |
C2 | 0.0208 (6) | 0.0227 (6) | 0.0234 (6) | −0.0006 (5) | 0.0006 (5) | −0.0010 (5) |
C3 | 0.0229 (6) | 0.0184 (6) | 0.0224 (6) | −0.0006 (5) | −0.0001 (5) | 0.0019 (5) |
C4 | 0.0206 (6) | 0.0188 (6) | 0.0208 (6) | −0.0020 (5) | −0.0004 (5) | 0.0037 (5) |
C5 | 0.0228 (6) | 0.0193 (6) | 0.0254 (6) | 0.0018 (5) | −0.0015 (5) | 0.0003 (5) |
C6 | 0.0207 (6) | 0.0238 (7) | 0.0270 (7) | 0.0004 (5) | −0.0052 (5) | 0.0009 (5) |
C7 | 0.0251 (6) | 0.0212 (6) | 0.0179 (6) | −0.0055 (5) | −0.0019 (5) | 0.0038 (5) |
C8 | 0.0251 (6) | 0.0234 (7) | 0.0217 (6) | −0.0009 (5) | 0.0046 (5) | 0.0000 (5) |
C9 | 0.0187 (6) | 0.0255 (7) | 0.0224 (6) | −0.0019 (5) | 0.0012 (5) | 0.0026 (5) |
C10 | 0.0254 (8) | 0.0575 (11) | 0.0703 (12) | 0.0182 (7) | −0.0136 (7) | −0.0335 (9) |
C11 | 0.0387 (8) | 0.0336 (8) | 0.0291 (7) | −0.0041 (6) | −0.0006 (6) | −0.0114 (6) |
C12 | 0.0201 (6) | 0.0181 (6) | 0.0197 (6) | −0.0007 (5) | −0.0004 (5) | 0.0023 (5) |
C13 | 0.0218 (6) | 0.0168 (6) | 0.0184 (6) | 0.0011 (5) | 0.0020 (5) | 0.0020 (5) |
C14 | 0.0209 (6) | 0.0189 (6) | 0.0178 (6) | −0.0012 (5) | −0.0009 (5) | 0.0037 (5) |
C15 | 0.0249 (6) | 0.0215 (6) | 0.0195 (6) | −0.0004 (5) | −0.0003 (5) | 0.0008 (5) |
C16 | 0.0266 (7) | 0.0264 (7) | 0.0218 (6) | −0.0045 (5) | −0.0051 (5) | 0.0008 (5) |
C17 | 0.0196 (6) | 0.0320 (7) | 0.0254 (6) | −0.0019 (5) | −0.0043 (5) | 0.0039 (5) |
C18 | 0.0204 (6) | 0.0277 (7) | 0.0255 (7) | 0.0022 (5) | 0.0000 (5) | 0.0020 (5) |
C19 | 0.0211 (6) | 0.0207 (6) | 0.0191 (6) | 0.0001 (5) | −0.0004 (5) | 0.0045 (5) |
C20 | 0.0223 (6) | 0.0224 (6) | 0.0237 (6) | 0.0030 (5) | 0.0019 (5) | −0.0023 (5) |
C21 | 0.0231 (6) | 0.0204 (6) | 0.0211 (6) | −0.0008 (5) | −0.0012 (5) | −0.0017 (5) |
O1—C1 | 1.2580 (15) | C10—H10B | 0.9800 |
O2—C5 | 1.3612 (16) | C10—H10C | 0.9800 |
O2—C10 | 1.4239 (17) | C11—H11A | 0.9800 |
O3—C7 | 1.3635 (15) | C11—H11B | 0.9800 |
O3—C11 | 1.4299 (17) | C11—H11C | 0.9800 |
O4—C13 | 1.3408 (15) | C12—C13 | 1.3987 (17) |
O4—H4O | 0.97 (2) | C12—C21 | 1.4258 (17) |
C1—C12 | 1.4634 (17) | C13—C14 | 1.4306 (17) |
C1—C2 | 1.4683 (18) | C14—C15 | 1.4133 (17) |
C2—C3 | 1.3414 (18) | C14—C19 | 1.4152 (17) |
C2—H2A | 0.9500 | C15—C16 | 1.3693 (18) |
C3—C4 | 1.4537 (17) | C15—H15A | 0.9500 |
C3—H3A | 0.9500 | C16—C17 | 1.4059 (19) |
C4—C9 | 1.3936 (18) | C16—H16A | 0.9500 |
C4—C5 | 1.4119 (17) | C17—C18 | 1.3680 (19) |
C5—C6 | 1.3832 (18) | C17—H17A | 0.9500 |
C6—C7 | 1.3919 (18) | C18—C19 | 1.4156 (17) |
C6—H6A | 0.9500 | C18—H18A | 0.9500 |
C7—C8 | 1.3902 (18) | C19—C20 | 1.4227 (18) |
C8—C9 | 1.3858 (18) | C20—C21 | 1.3580 (17) |
C8—H8A | 0.9500 | C20—H20A | 0.9500 |
C9—H9A | 0.9500 | C21—H21A | 0.9500 |
C10—H10A | 0.9800 | ||
C5—O2—C10 | 117.97 (11) | O3—C11—H11A | 109.5 |
C7—O3—C11 | 117.44 (10) | O3—C11—H11B | 109.5 |
C13—O4—H4O | 102.7 (12) | H11A—C11—H11B | 109.5 |
O1—C1—C12 | 119.77 (11) | O3—C11—H11C | 109.5 |
O1—C1—C2 | 119.13 (11) | H11A—C11—H11C | 109.5 |
C12—C1—C2 | 121.11 (11) | H11B—C11—H11C | 109.5 |
C3—C2—C1 | 120.65 (11) | C13—C12—C21 | 118.15 (11) |
C3—C2—H2A | 119.7 | C13—C12—C1 | 119.35 (11) |
C1—C2—H2A | 119.7 | C21—C12—C1 | 122.50 (11) |
C2—C3—C4 | 127.94 (12) | O4—C13—C12 | 121.93 (11) |
C2—C3—H3A | 116.0 | O4—C13—C14 | 116.85 (11) |
C4—C3—H3A | 116.0 | C12—C13—C14 | 121.22 (11) |
C9—C4—C5 | 116.67 (11) | C15—C14—C19 | 119.82 (11) |
C9—C4—C3 | 123.29 (11) | C15—C14—C13 | 121.53 (11) |
C5—C4—C3 | 120.00 (11) | C19—C14—C13 | 118.65 (11) |
O2—C5—C6 | 123.18 (11) | C16—C15—C14 | 120.33 (12) |
O2—C5—C4 | 115.50 (11) | C16—C15—H15A | 119.8 |
C6—C5—C4 | 121.32 (12) | C14—C15—H15A | 119.8 |
C5—C6—C7 | 119.80 (11) | C15—C16—C17 | 120.18 (12) |
C5—C6—H6A | 120.1 | C15—C16—H16A | 119.9 |
C7—C6—H6A | 120.1 | C17—C16—H16A | 119.9 |
O3—C7—C8 | 124.91 (11) | C18—C17—C16 | 120.48 (12) |
O3—C7—C6 | 114.42 (11) | C18—C17—H17A | 119.8 |
C8—C7—C6 | 120.67 (11) | C16—C17—H17A | 119.8 |
C9—C8—C7 | 118.31 (12) | C17—C18—C19 | 120.94 (12) |
C9—C8—H8A | 120.8 | C17—C18—H18A | 119.5 |
C7—C8—H8A | 120.8 | C19—C18—H18A | 119.5 |
C8—C9—C4 | 123.21 (12) | C14—C19—C18 | 118.24 (11) |
C8—C9—H9A | 118.4 | C14—C19—C20 | 119.51 (11) |
C4—C9—H9A | 118.4 | C18—C19—C20 | 122.24 (11) |
O2—C10—H10A | 109.5 | C21—C20—C19 | 120.66 (11) |
O2—C10—H10B | 109.5 | C21—C20—H20A | 119.7 |
H10A—C10—H10B | 109.5 | C19—C20—H20A | 119.7 |
O2—C10—H10C | 109.5 | C20—C21—C12 | 121.79 (11) |
H10A—C10—H10C | 109.5 | C20—C21—H21A | 119.1 |
H10B—C10—H10C | 109.5 | C12—C21—H21A | 119.1 |
O1—C1—C2—C3 | 0.91 (18) | C2—C1—C12—C21 | −4.86 (18) |
C12—C1—C2—C3 | −179.00 (11) | C21—C12—C13—O4 | −179.06 (10) |
C1—C2—C3—C4 | −178.69 (11) | C1—C12—C13—O4 | 0.41 (17) |
C2—C3—C4—C9 | 9.1 (2) | C21—C12—C13—C14 | 0.81 (17) |
C2—C3—C4—C5 | −173.07 (12) | C1—C12—C13—C14 | −179.73 (10) |
C10—O2—C5—C6 | 1.6 (2) | O4—C13—C14—C15 | −1.54 (17) |
C10—O2—C5—C4 | −178.52 (14) | C12—C13—C14—C15 | 178.59 (11) |
C9—C4—C5—O2 | 178.52 (11) | O4—C13—C14—C19 | 178.34 (10) |
C3—C4—C5—O2 | 0.59 (17) | C12—C13—C14—C19 | −1.53 (17) |
C9—C4—C5—C6 | −1.56 (18) | C19—C14—C15—C16 | −0.24 (18) |
C3—C4—C5—C6 | −179.48 (11) | C13—C14—C15—C16 | 179.64 (11) |
O2—C5—C6—C7 | −179.17 (12) | C14—C15—C16—C17 | −0.57 (19) |
C4—C5—C6—C7 | 0.91 (19) | C15—C16—C17—C18 | 0.90 (19) |
C11—O3—C7—C8 | 3.18 (17) | C16—C17—C18—C19 | −0.38 (19) |
C11—O3—C7—C6 | −177.12 (11) | C15—C14—C19—C18 | 0.74 (17) |
C5—C6—C7—O3 | −179.88 (11) | C13—C14—C19—C18 | −179.15 (11) |
C5—C6—C7—C8 | −0.17 (19) | C15—C14—C19—C20 | −179.25 (11) |
O3—C7—C8—C9 | 179.82 (11) | C13—C14—C19—C20 | 0.86 (17) |
C6—C7—C8—C9 | 0.13 (18) | C17—C18—C19—C14 | −0.43 (18) |
C7—C8—C9—C4 | −0.87 (19) | C17—C18—C19—C20 | 179.56 (12) |
C5—C4—C9—C8 | 1.56 (18) | C14—C19—C20—C21 | 0.52 (18) |
C3—C4—C9—C8 | 179.41 (11) | C18—C19—C20—C21 | −179.47 (12) |
O1—C1—C12—C13 | −4.21 (17) | C19—C20—C21—C12 | −1.29 (19) |
C2—C1—C12—C13 | 175.70 (11) | C13—C12—C21—C20 | 0.62 (18) |
O1—C1—C12—C21 | 175.23 (11) | C1—C12—C21—C20 | −178.83 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1 | 0.97 (2) | 1.59 (2) | 2.499 (1) | 155.1 (19) |
C10—H10A···O1i | 0.98 | 2.57 | 3.538 (2) | 167 |
C11—H11B···O2ii | 0.98 | 2.58 | 3.442 (2) | 147 |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x+1/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1 | 0.97 (2) | 1.59 (2) | 2.499 (1) | 155.1 (19) |
C10—H10A···O1i | 0.98 | 2.57 | 3.538 (2) | 167 |
C11—H11B···O2ii | 0.98 | 2.58 | 3.442 (2) | 147 |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x+1/2, y−1/2, −z+3/2. |
References
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