Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047915/is2214sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047915/is2214Isup2.hkl |
CCDC reference: 667302
Methyl-2-bromomethyl-3-phenyl-propenoate (10 mmol) was treated with eugenol (10 mmol) in the presence of potassium carbonate in acetone at reflux temperature for 3 h. The pure ester of methyl-3-phenyl-2-(2-methoxy-4-prop-2-enyl)phenoxy methyl-prop-2-noate was obtained after silica gel column chromatography (3% EtOAc–hexane). Hydrolysis of this ester was carried out with KOH in aqueous 1,4-dioxane at room temperature. The reaction mixture was acidified and the precipitated acid was purified by recrystalization. Finally the acid was treated with TFAA and the reaction mixture refluxed in dichloromethane for 1 h. It was further purified by column chromatography (silica gel, 3% EtOAc–hexane).
H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.
The chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring which plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001). The naturally occurring classes of compounds to which they belong, the benzylidine chroman-4-ones have identified as a potential source of new anti-fungal agents (Kang et al., 2004).
The geometric parameters in the compound, (I), agree with the reported values of similar structure (Wu, Xu, Zhou & Liang, 2005; Wu, Xu, Wan et al., 2005; Schollmeyer et al., 2005; Nissa et al., 2001). The phenyl ring makes a dihedral angle of 39.97 (4)° with the benzene ring of chromanone unit. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by a weak intermolecular C—H···O interaction.
For related literature see: Tillekeratne et al. (2001); Nissa et al. (2001); Kang et al. (2004); Wu, Xu, Zhou & Liang (2005); Wu, Xu, Wan et al. (2005); Schollmeyer et al. (2005).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
C20H18O3 | F(000) = 648 |
Mr = 306.34 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 31265 reflections |
a = 8.9229 (5) Å | θ = 2.2–30.0° |
b = 14.0910 (6) Å | µ = 0.09 mm−1 |
c = 12.3493 (6) Å | T = 150 K |
β = 92.930 (4)° | Prism, yellow |
V = 1550.68 (13) Å3 | 0.50 × 0.42 × 0.36 mm |
Z = 4 |
Stoe IPDS2 diffractometer | 4481 independent reflections |
Radiation source: fine-focus sealed tube | 3495 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 30.0°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.958, Tmax = 0.969 | l = −17→17 |
27302 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3 |
4481 reflections | (Δ/σ)max = 0.001 |
209 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C20H18O3 | V = 1550.68 (13) Å3 |
Mr = 306.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.9229 (5) Å | µ = 0.09 mm−1 |
b = 14.0910 (6) Å | T = 150 K |
c = 12.3493 (6) Å | 0.50 × 0.42 × 0.36 mm |
β = 92.930 (4)° |
Stoe IPDS2 diffractometer | 4481 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | 3495 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.969 | Rint = 0.057 |
27302 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.40 e Å−3 |
4481 reflections | Δρmin = −0.27 e Å−3 |
209 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 | −0.00323 (10) | 0.10788 (6) | 0.71245 (6) | 0.0365 (2) | |
O2 | 0.19644 (10) | 0.00693 (6) | 0.99286 (7) | 0.0379 (2) | |
O3 | −0.01473 (11) | 0.28696 (6) | 0.66460 (7) | 0.0391 (2) | |
C1 | 0.01490 (13) | −0.20158 (8) | 0.77596 (9) | 0.0320 (2) | |
C2 | −0.11928 (14) | −0.19972 (9) | 0.71231 (10) | 0.0367 (2) | |
H2 | −0.1786 | −0.1454 | 0.7111 | 0.044* | |
C3 | −0.16463 (15) | −0.27785 (10) | 0.65112 (11) | 0.0421 (3) | |
H3 | −0.2531 | −0.2751 | 0.6080 | 0.051* | |
C4 | −0.07937 (16) | −0.36015 (9) | 0.65349 (11) | 0.0428 (3) | |
H4 | −0.1094 | −0.4120 | 0.6112 | 0.051* | |
C5 | 0.05080 (15) | −0.36449 (9) | 0.71928 (12) | 0.0424 (3) | |
H5 | 0.1074 | −0.4199 | 0.7226 | 0.051* | |
C6 | 0.09676 (14) | −0.28618 (8) | 0.78026 (10) | 0.0364 (2) | |
H6 | 0.1837 | −0.2900 | 0.8249 | 0.044* | |
C7 | 0.07444 (13) | −0.12215 (8) | 0.84140 (9) | 0.0319 (2) | |
H7 | 0.1408 | −0.1392 | 0.8986 | 0.038* | |
C8 | 0.04848 (12) | −0.02850 (8) | 0.83192 (9) | 0.0306 (2) | |
C9 | 0.12098 (12) | 0.03627 (8) | 0.91420 (9) | 0.0302 (2) | |
C10 | 0.09940 (12) | 0.13854 (8) | 0.89403 (9) | 0.0293 (2) | |
C11 | 0.04207 (12) | 0.16868 (8) | 0.79283 (8) | 0.0303 (2) | |
C12 | −0.05548 (14) | 0.01735 (8) | 0.74838 (9) | 0.0341 (2) | |
H12A | −0.0681 | −0.0246 | 0.6863 | 0.041* | |
H12B | −0.1530 | 0.0256 | 0.7784 | 0.041* | |
C13 | 0.14881 (13) | 0.20629 (8) | 0.97125 (9) | 0.0315 (2) | |
H13 | 0.1874 | 0.1863 | 1.0388 | 0.038* | |
C14 | 0.14090 (13) | 0.30157 (8) | 0.94844 (9) | 0.0333 (2) | |
C15 | 0.08513 (13) | 0.33094 (8) | 0.84531 (9) | 0.0334 (2) | |
H15 | 0.0805 | 0.3954 | 0.8292 | 0.040* | |
C16 | 0.03716 (13) | 0.26584 (8) | 0.76749 (9) | 0.0317 (2) | |
C17 | −0.01812 (15) | 0.38441 (9) | 0.63519 (10) | 0.0392 (3) | |
H17A | −0.0826 | 0.4183 | 0.6816 | 0.059* | |
H17B | −0.0555 | 0.3906 | 0.5612 | 0.059* | |
H17C | 0.0814 | 0.4102 | 0.6428 | 0.059* | |
C18 | 0.19189 (16) | 0.37561 (9) | 1.03162 (10) | 0.0399 (3) | |
H18A | 0.1044 | 0.4058 | 1.0600 | 0.048* | |
H18B | 0.2466 | 0.3445 | 1.0915 | 0.048* | |
C19 | 0.28911 (15) | 0.44939 (10) | 0.98556 (11) | 0.0423 (3) | |
H19 | 0.3776 | 0.4293 | 0.9561 | 0.051* | |
C20 | 0.25975 (18) | 0.54132 (10) | 0.98312 (12) | 0.0499 (3) | |
H20A | 0.1724 | 0.5642 | 1.0117 | 0.060* | |
H20B | 0.3265 | 0.5831 | 0.9528 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0521 (5) | 0.0291 (4) | 0.0270 (4) | −0.0020 (3) | −0.0094 (3) | −0.0009 (3) |
O2 | 0.0440 (5) | 0.0327 (4) | 0.0355 (4) | 0.0021 (3) | −0.0134 (3) | 0.0024 (3) |
O3 | 0.0548 (5) | 0.0308 (4) | 0.0300 (4) | −0.0029 (3) | −0.0132 (4) | 0.0046 (3) |
C1 | 0.0350 (5) | 0.0296 (5) | 0.0315 (5) | −0.0022 (4) | 0.0018 (4) | −0.0003 (4) |
C2 | 0.0376 (6) | 0.0329 (5) | 0.0393 (6) | −0.0017 (4) | −0.0030 (5) | −0.0009 (4) |
C3 | 0.0447 (7) | 0.0422 (6) | 0.0387 (6) | −0.0107 (5) | −0.0037 (5) | −0.0025 (5) |
C4 | 0.0521 (7) | 0.0367 (6) | 0.0402 (6) | −0.0114 (5) | 0.0080 (5) | −0.0089 (5) |
C5 | 0.0449 (6) | 0.0305 (6) | 0.0526 (7) | −0.0021 (5) | 0.0100 (6) | −0.0058 (5) |
C6 | 0.0360 (6) | 0.0305 (5) | 0.0429 (6) | −0.0007 (4) | 0.0028 (5) | −0.0007 (4) |
C7 | 0.0326 (5) | 0.0308 (5) | 0.0316 (5) | −0.0003 (4) | −0.0030 (4) | −0.0004 (4) |
C8 | 0.0328 (5) | 0.0302 (5) | 0.0283 (5) | 0.0004 (4) | −0.0030 (4) | −0.0012 (4) |
C9 | 0.0318 (5) | 0.0300 (5) | 0.0282 (5) | 0.0009 (4) | −0.0038 (4) | 0.0004 (4) |
C10 | 0.0315 (5) | 0.0291 (5) | 0.0269 (5) | 0.0004 (4) | −0.0032 (4) | −0.0003 (4) |
C11 | 0.0332 (5) | 0.0305 (5) | 0.0264 (5) | 0.0000 (4) | −0.0042 (4) | −0.0019 (4) |
C12 | 0.0412 (6) | 0.0284 (5) | 0.0316 (5) | −0.0010 (4) | −0.0081 (4) | −0.0004 (4) |
C13 | 0.0363 (5) | 0.0314 (5) | 0.0262 (5) | −0.0004 (4) | −0.0051 (4) | 0.0002 (4) |
C14 | 0.0382 (6) | 0.0320 (5) | 0.0292 (5) | −0.0022 (4) | −0.0045 (4) | −0.0019 (4) |
C15 | 0.0391 (6) | 0.0288 (5) | 0.0319 (5) | −0.0007 (4) | −0.0043 (4) | 0.0004 (4) |
C16 | 0.0344 (5) | 0.0327 (5) | 0.0273 (5) | 0.0005 (4) | −0.0051 (4) | 0.0021 (4) |
C17 | 0.0461 (6) | 0.0330 (6) | 0.0373 (6) | −0.0018 (5) | −0.0088 (5) | 0.0083 (4) |
C18 | 0.0530 (7) | 0.0343 (6) | 0.0316 (6) | −0.0043 (5) | −0.0068 (5) | −0.0029 (4) |
C19 | 0.0424 (6) | 0.0452 (7) | 0.0384 (6) | −0.0069 (5) | −0.0058 (5) | −0.0043 (5) |
C20 | 0.0605 (8) | 0.0417 (7) | 0.0456 (7) | −0.0116 (6) | −0.0149 (6) | 0.0064 (6) |
O1—C11 | 1.3570 (13) | C18—C14 | 1.5176 (16) |
O1—C12 | 1.4362 (14) | C18—H18A | 0.9700 |
O3—C16 | 1.3628 (13) | C18—H18B | 0.9700 |
O3—C17 | 1.4204 (14) | C6—C5 | 1.3860 (17) |
O2—C9 | 1.2252 (13) | C6—H6 | 0.9300 |
C10—C11 | 1.3923 (15) | C17—H17A | 0.9600 |
C10—C13 | 1.4044 (15) | C17—H17B | 0.9600 |
C10—C9 | 1.4734 (15) | C17—H17C | 0.9600 |
C9—C8 | 1.4889 (15) | C12—H12A | 0.9700 |
C8—C7 | 1.3439 (15) | C12—H12B | 0.9700 |
C8—C12 | 1.4981 (15) | C19—C20 | 1.322 (2) |
C13—C14 | 1.3728 (16) | C19—H19 | 0.9300 |
C13—H13 | 0.9300 | C2—C3 | 1.3839 (17) |
C15—C16 | 1.3806 (15) | C2—H2 | 0.9300 |
C15—C14 | 1.4057 (15) | C3—C4 | 1.386 (2) |
C15—H15 | 0.9300 | C3—H3 | 0.9300 |
C1—C6 | 1.3977 (16) | C5—C4 | 1.384 (2) |
C1—C2 | 1.3985 (17) | C5—H5 | 0.9300 |
C1—C7 | 1.4643 (15) | C4—H4 | 0.9300 |
C11—C16 | 1.4047 (15) | C20—H20A | 0.9300 |
C7—H7 | 0.9300 | C20—H20B | 0.9300 |
C18—C19 | 1.4858 (19) | ||
C11—O1—C12 | 115.08 (8) | C5—C6—H6 | 119.4 |
C16—O3—C17 | 116.83 (9) | C1—C6—H6 | 119.4 |
C11—C10—C13 | 119.36 (10) | O3—C17—H17A | 109.5 |
C11—C10—C9 | 119.27 (10) | O3—C17—H17B | 109.5 |
C13—C10—C9 | 121.08 (10) | H17A—C17—H17B | 109.5 |
O2—C9—C10 | 121.73 (10) | O3—C17—H17C | 109.5 |
O2—C9—C8 | 122.42 (10) | H17A—C17—H17C | 109.5 |
C10—C9—C8 | 115.83 (9) | H17B—C17—H17C | 109.5 |
C7—C8—C9 | 118.40 (10) | O1—C12—C8 | 113.36 (9) |
C7—C8—C12 | 125.55 (10) | O1—C12—H12A | 108.9 |
C9—C8—C12 | 115.95 (9) | C8—C12—H12A | 108.9 |
C14—C13—C10 | 120.96 (10) | O1—C12—H12B | 108.9 |
C14—C13—H13 | 119.5 | C8—C12—H12B | 108.9 |
C10—C13—H13 | 119.5 | H12A—C12—H12B | 107.7 |
C16—C15—C14 | 121.19 (10) | C13—C14—C15 | 119.07 (10) |
C16—C15—H15 | 119.4 | C13—C14—C18 | 121.53 (10) |
C14—C15—H15 | 119.4 | C15—C14—C18 | 119.40 (10) |
C6—C1—C2 | 117.91 (11) | C20—C19—C18 | 125.15 (14) |
C6—C1—C7 | 117.18 (10) | C20—C19—H19 | 117.4 |
C2—C1—C7 | 124.89 (11) | C18—C19—H19 | 117.4 |
O1—C11—C10 | 123.10 (10) | C3—C2—C1 | 120.66 (12) |
O1—C11—C16 | 116.60 (9) | C3—C2—H2 | 119.7 |
C10—C11—C16 | 120.20 (10) | C1—C2—H2 | 119.7 |
O3—C16—C15 | 125.62 (10) | C2—C3—C4 | 120.60 (12) |
O3—C16—C11 | 115.20 (10) | C2—C3—H3 | 119.7 |
C15—C16—C11 | 119.18 (10) | C4—C3—H3 | 119.7 |
C8—C7—C1 | 130.27 (11) | C4—C5—C6 | 119.98 (12) |
C8—C7—H7 | 114.9 | C4—C5—H5 | 120.0 |
C1—C7—H7 | 114.9 | C6—C5—H5 | 120.0 |
C19—C18—C14 | 112.49 (11) | C5—C4—C3 | 119.50 (12) |
C19—C18—H18A | 109.1 | C5—C4—H4 | 120.3 |
C14—C18—H18A | 109.1 | C3—C4—H4 | 120.3 |
C19—C18—H18B | 109.1 | C19—C20—H20A | 120.0 |
C14—C18—H18B | 109.1 | C19—C20—H20B | 120.0 |
H18A—C18—H18B | 107.8 | H20A—C20—H20B | 120.0 |
C5—C6—C1 | 121.25 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.58 | 3.4364 (16) | 153 |
C7—H7···O2 | 0.93 | 2.40 | 2.7899 (14) | 105 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H18O3 |
Mr | 306.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 8.9229 (5), 14.0910 (6), 12.3493 (6) |
β (°) | 92.930 (4) |
V (Å3) | 1550.68 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.42 × 0.36 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.958, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27302, 4481, 3495 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.129, 1.06 |
No. of reflections | 4481 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.27 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.58 | 3.4364 (16) | 153 |
C7—H7···O2 | 0.93 | 2.40 | 2.7899 (14) | 105 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
The chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring which plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001). The naturally occurring classes of compounds to which they belong, the benzylidine chroman-4-ones have identified as a potential source of new anti-fungal agents (Kang et al., 2004).
The geometric parameters in the compound, (I), agree with the reported values of similar structure (Wu, Xu, Zhou & Liang, 2005; Wu, Xu, Wan et al., 2005; Schollmeyer et al., 2005; Nissa et al., 2001). The phenyl ring makes a dihedral angle of 39.97 (4)° with the benzene ring of chromanone unit. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by a weak intermolecular C—H···O interaction.