Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050258/is2219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050258/is2219Isup2.hkl |
CCDC reference: 667405
Bromomethyl-3-phenyl-propenoate (10 mmol) was treated with beta-napthanol (10 mmol) in the presence of potassium carbonate in acetone at reflux temperature for 3 h. The napthoxy ester of methyl- 3-phenyl-2-(2-methoxy-4-prop-2-enyl) phenoxy methyl-prop-2-enoate 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 (C—H = 0.95 or 0.99 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs have been merged.
The chromanone moiety present in the title compound consisting of the pyrone and benzene rings, 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 benzylidene chroman-4-ones, have identified as a potential source of new anti-fungal agents (Kang et al., 2004).
The geometric parameters in the title compound agree with the reported values of similar structure (Puviarasan et al., 1998; Wu et al., 2005a,b; Schollmeyer et al., 2005; Nissa et al., 2001). The dihedral angles between the phenyl ring and the benzene ring of chromanone unit in the two crystallographically independent molecules are 56.17 (4) and 55.62 (7)°.
The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π interactions.
For related literature see: Puviarasan et al. (1998); Tillekeratne et al. (2001); Nissa et al. (2001); Kang et al. (2004); Wu et al. (2005a,b); Schollmeyer et al. (2005). Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings,
respectively.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (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 asymmetric unit of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
C20H14O2 | F(000) = 1200 |
Mr = 286.31 | Dx = 1.338 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 30955 reflections |
a = 12.3567 (6) Å | θ = 1.7–27.2° |
b = 11.2675 (5) Å | µ = 0.09 mm−1 |
c = 20.4103 (12) Å | T = 150 K |
V = 2841.7 (3) Å3 | Prism, yellow |
Z = 8 | 0.32 × 0.23 × 0.18 mm |
Stoe IPDS2 diffractometer | 2881 independent reflections |
Radiation source: fine-focus sealed tube | 2120 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
rotation method scans | h = −15→15 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.973, Tmax = 0.985 | l = −25→25 |
33648 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0267P)2] where P = (Fo2 + 2Fc2)/3 |
2881 reflections | (Δ/σ)max = 0.001 |
398 parameters | Δρmax = 0.12 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C20H14O2 | V = 2841.7 (3) Å3 |
Mr = 286.31 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 12.3567 (6) Å | µ = 0.09 mm−1 |
b = 11.2675 (5) Å | T = 150 K |
c = 20.4103 (12) Å | 0.32 × 0.23 × 0.18 mm |
Stoe IPDS2 diffractometer | 2881 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2120 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.985 | Rint = 0.105 |
33648 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.12 e Å−3 |
2881 reflections | Δρmin = −0.14 e Å−3 |
398 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 | ||
C1 | 0.1622 (2) | −0.0440 (3) | 0.23909 (15) | 0.0308 (6) | |
C2 | 0.1523 (2) | −0.1118 (3) | 0.29624 (14) | 0.0377 (7) | |
H2 | 0.2018 | −0.1746 | 0.3042 | 0.045* | |
C3 | 0.0716 (2) | −0.0885 (3) | 0.34113 (16) | 0.0444 (8) | |
H3 | 0.0661 | −0.1352 | 0.3797 | 0.053* | |
C4 | −0.0014 (3) | 0.0026 (2) | 0.3303 (2) | 0.0384 (10) | |
H4 | −0.0560 | 0.0195 | 0.3617 | 0.046* | |
C5 | 0.0056 (2) | 0.0686 (3) | 0.27360 (17) | 0.0380 (7) | |
H5 | −0.0453 | 0.1301 | 0.2657 | 0.046* | |
C6 | 0.0866 (2) | 0.0461 (3) | 0.22768 (16) | 0.0334 (7) | |
H6 | 0.0905 | 0.0919 | 0.1887 | 0.040* | |
C7 | 0.2507 (2) | −0.0713 (2) | 0.19390 (15) | 0.0322 (6) | |
H7 | 0.2714 | −0.1524 | 0.1925 | 0.039* | |
C8 | 0.3068 (3) | 0.0006 (2) | 0.1543 (2) | 0.0292 (9) | |
C9 | 0.3951 (2) | −0.0516 (2) | 0.11341 (15) | 0.0317 (7) | |
C10 | 0.4700 (2) | 0.0332 (3) | 0.08277 (15) | 0.0307 (7) | |
C11 | 0.5574 (3) | −0.0012 (2) | 0.0393 (2) | 0.0283 (9) | |
C12 | 0.5704 (2) | −0.1172 (3) | 0.01372 (14) | 0.0341 (7) | |
H12 | 0.5198 | −0.1770 | 0.0255 | 0.041* | |
C13 | 0.6539 (2) | −0.1451 (3) | −0.02748 (15) | 0.0384 (7) | |
H13 | 0.6595 | −0.2233 | −0.0446 | 0.046* | |
C14 | 0.7310 (3) | −0.0600 (3) | −0.04466 (16) | 0.0406 (8) | |
H14 | 0.7897 | −0.0804 | −0.0726 | 0.049* | |
C15 | 0.7213 (3) | 0.0530 (3) | −0.02093 (17) | 0.0395 (9) | |
H15 | 0.7739 | 0.1107 | −0.0326 | 0.047* | |
C16 | 0.6352 (2) | 0.0857 (2) | 0.02037 (14) | 0.0325 (7) | |
C17 | 0.6268 (2) | 0.2029 (3) | 0.04455 (14) | 0.0372 (7) | |
H17 | 0.6802 | 0.2598 | 0.0330 | 0.045* | |
C18 | 0.5439 (2) | 0.2354 (2) | 0.08387 (15) | 0.0362 (7) | |
H18 | 0.5388 | 0.3149 | 0.0991 | 0.043* | |
C19 | 0.4647 (2) | 0.1511 (3) | 0.10228 (15) | 0.0319 (7) | |
C20 | 0.2890 (2) | 0.1306 (2) | 0.14782 (16) | 0.0354 (7) | |
H20A | 0.2442 | 0.1460 | 0.1085 | 0.043* | |
H20B | 0.2484 | 0.1593 | 0.1865 | 0.043* | |
C21 | 0.5995 (2) | 0.5378 (3) | 0.18920 (15) | 0.0312 (7) | |
C22 | 0.6709 (2) | 0.4432 (3) | 0.19898 (16) | 0.0357 (7) | |
H22 | 0.6618 | 0.3924 | 0.2357 | 0.043* | |
C23 | 0.7547 (2) | 0.4230 (3) | 0.15543 (17) | 0.0390 (7) | |
H23 | 0.8018 | 0.3574 | 0.1619 | 0.047* | |
C24 | 0.7703 (3) | 0.4972 (2) | 0.1031 (2) | 0.0413 (10) | |
H24 | 0.8287 | 0.4834 | 0.0738 | 0.050* | |
C25 | 0.7012 (2) | 0.5924 (3) | 0.09264 (16) | 0.0408 (7) | |
H25 | 0.7112 | 0.6430 | 0.0559 | 0.049* | |
C26 | 0.6172 (2) | 0.6127 (2) | 0.13634 (14) | 0.0358 (7) | |
H26 | 0.5710 | 0.6792 | 0.1300 | 0.043* | |
C27 | 0.5093 (2) | 0.5654 (3) | 0.23332 (14) | 0.0323 (7) | |
H27 | 0.4904 | 0.6470 | 0.2354 | 0.039* | |
C28 | 0.4494 (3) | 0.4940 (2) | 0.2711 (2) | 0.0311 (10) | |
C29 | 0.3629 (2) | 0.5486 (3) | 0.31194 (14) | 0.0310 (7) | |
C30 | 0.2851 (2) | 0.4663 (3) | 0.34178 (15) | 0.0290 (6) | |
C31 | 0.2010 (3) | 0.5032 (2) | 0.3862 (2) | 0.0285 (9) | |
C32 | 0.1977 (2) | 0.6160 (3) | 0.41633 (14) | 0.0335 (7) | |
H32 | 0.2536 | 0.6717 | 0.4076 | 0.040* | |
C33 | 0.1151 (2) | 0.6464 (3) | 0.45793 (14) | 0.0378 (7) | |
H33 | 0.1158 | 0.7222 | 0.4783 | 0.045* | |
C34 | 0.0293 (3) | 0.5679 (3) | 0.47106 (17) | 0.0391 (8) | |
H34 | −0.0288 | 0.5914 | 0.4986 | 0.047* | |
C35 | 0.0308 (3) | 0.4586 (3) | 0.44398 (16) | 0.0363 (8) | |
H35 | −0.0261 | 0.4046 | 0.4535 | 0.044* | |
C36 | 0.1155 (2) | 0.4227 (3) | 0.40164 (14) | 0.0326 (7) | |
C37 | 0.1164 (2) | 0.3071 (2) | 0.37394 (14) | 0.0354 (7) | |
H37 | 0.0585 | 0.2542 | 0.3833 | 0.042* | |
C38 | 0.1981 (2) | 0.2705 (3) | 0.33438 (14) | 0.0353 (7) | |
H38 | 0.1981 | 0.1923 | 0.3170 | 0.042* | |
C39 | 0.2830 (2) | 0.3498 (3) | 0.31937 (15) | 0.0310 (7) | |
C40 | 0.4609 (2) | 0.3623 (2) | 0.27652 (16) | 0.0354 (7) | |
H40A | 0.5029 | 0.3326 | 0.2386 | 0.042* | |
H40B | 0.5020 | 0.3431 | 0.3168 | 0.042* | |
O1 | 0.40678 (16) | −0.16006 (19) | 0.10971 (12) | 0.0423 (6) | |
O2 | 0.38869 (16) | 0.19617 (18) | 0.14242 (10) | 0.0380 (5) | |
O3 | 0.35498 (16) | 0.65771 (18) | 0.31632 (12) | 0.0381 (5) | |
O4 | 0.35807 (14) | 0.30302 (19) | 0.27852 (10) | 0.0381 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0286 (15) | 0.0270 (16) | 0.0369 (18) | −0.0049 (13) | −0.0027 (14) | −0.0051 (15) |
C2 | 0.0379 (17) | 0.0339 (16) | 0.0413 (18) | 0.0000 (13) | −0.0016 (14) | 0.0032 (14) |
C3 | 0.0447 (18) | 0.046 (2) | 0.0428 (19) | −0.0055 (15) | 0.0031 (15) | 0.0042 (16) |
C4 | 0.0350 (18) | 0.039 (2) | 0.041 (2) | −0.0061 (13) | 0.0028 (17) | −0.0058 (13) |
C5 | 0.0272 (15) | 0.0331 (16) | 0.054 (2) | −0.0025 (12) | −0.0041 (15) | −0.0053 (15) |
C6 | 0.0317 (16) | 0.0319 (18) | 0.0367 (18) | −0.0046 (13) | −0.0026 (14) | 0.0014 (14) |
C7 | 0.0293 (14) | 0.0276 (14) | 0.0398 (17) | −0.0014 (12) | −0.0023 (13) | −0.0023 (13) |
C8 | 0.0285 (18) | 0.026 (2) | 0.033 (2) | 0.0008 (11) | −0.0053 (16) | −0.0023 (11) |
C9 | 0.0310 (16) | 0.0253 (19) | 0.0390 (18) | −0.0029 (12) | −0.0047 (13) | −0.0002 (14) |
C10 | 0.0331 (17) | 0.0302 (15) | 0.0289 (17) | −0.0031 (14) | −0.0063 (14) | −0.0002 (15) |
C11 | 0.0317 (19) | 0.024 (2) | 0.029 (2) | −0.0013 (11) | −0.0034 (15) | 0.0002 (11) |
C12 | 0.0392 (17) | 0.0302 (17) | 0.0329 (17) | −0.0038 (13) | −0.0001 (13) | −0.0030 (13) |
C13 | 0.0442 (17) | 0.0337 (17) | 0.0372 (17) | −0.0009 (14) | −0.0015 (15) | −0.0044 (14) |
C14 | 0.0405 (18) | 0.0408 (19) | 0.040 (2) | −0.0040 (15) | 0.0070 (15) | −0.0032 (16) |
C15 | 0.0437 (19) | 0.034 (2) | 0.041 (2) | −0.0082 (15) | 0.0055 (16) | −0.0024 (16) |
C16 | 0.0343 (16) | 0.0326 (17) | 0.0305 (16) | −0.0068 (13) | −0.0044 (13) | −0.0010 (12) |
C17 | 0.0395 (17) | 0.0301 (16) | 0.0419 (17) | −0.0087 (13) | 0.0006 (14) | −0.0025 (13) |
C18 | 0.0447 (17) | 0.0230 (15) | 0.0409 (17) | −0.0063 (13) | 0.0019 (15) | −0.0041 (13) |
C19 | 0.0340 (15) | 0.0295 (15) | 0.0323 (17) | 0.0000 (13) | −0.0036 (14) | −0.0015 (13) |
C20 | 0.0322 (16) | 0.0315 (17) | 0.0426 (18) | −0.0022 (12) | −0.0007 (14) | 0.0005 (13) |
C21 | 0.0322 (17) | 0.0298 (16) | 0.0315 (17) | −0.0020 (14) | −0.0035 (14) | −0.0061 (15) |
C22 | 0.0303 (16) | 0.0330 (18) | 0.0439 (19) | −0.0034 (13) | −0.0071 (14) | −0.0030 (14) |
C23 | 0.0307 (15) | 0.0337 (16) | 0.053 (2) | 0.0004 (13) | −0.0015 (15) | −0.0083 (15) |
C24 | 0.0343 (18) | 0.045 (2) | 0.045 (2) | −0.0030 (13) | 0.0066 (17) | −0.0139 (15) |
C25 | 0.0446 (17) | 0.0393 (18) | 0.0384 (18) | −0.0059 (15) | 0.0011 (15) | −0.0025 (14) |
C26 | 0.0333 (15) | 0.0339 (15) | 0.0401 (16) | 0.0003 (13) | −0.0018 (14) | −0.0004 (14) |
C27 | 0.0335 (16) | 0.0285 (15) | 0.0349 (17) | 0.0014 (12) | −0.0082 (14) | −0.0036 (13) |
C28 | 0.0295 (18) | 0.030 (2) | 0.033 (2) | 0.0011 (12) | −0.0031 (16) | −0.0040 (12) |
C29 | 0.0320 (17) | 0.0292 (19) | 0.0317 (16) | 0.0006 (12) | −0.0043 (13) | −0.0036 (14) |
C30 | 0.0288 (16) | 0.0269 (15) | 0.0311 (17) | 0.0020 (13) | −0.0020 (13) | −0.0004 (15) |
C31 | 0.0304 (19) | 0.031 (2) | 0.024 (2) | 0.0022 (11) | −0.0061 (15) | 0.0011 (11) |
C32 | 0.0327 (16) | 0.0326 (16) | 0.0353 (17) | 0.0001 (12) | −0.0014 (13) | −0.0003 (14) |
C33 | 0.0413 (16) | 0.0329 (16) | 0.0392 (17) | 0.0021 (13) | 0.0041 (14) | −0.0030 (13) |
C34 | 0.0342 (16) | 0.046 (2) | 0.037 (2) | 0.0023 (15) | 0.0035 (14) | 0.0011 (16) |
C35 | 0.0310 (16) | 0.043 (2) | 0.035 (2) | −0.0028 (15) | 0.0002 (14) | 0.0057 (16) |
C36 | 0.0360 (16) | 0.0308 (16) | 0.0312 (16) | −0.0001 (14) | −0.0057 (14) | 0.0029 (13) |
C37 | 0.0376 (16) | 0.0309 (16) | 0.0377 (16) | −0.0068 (13) | −0.0062 (14) | 0.0053 (13) |
C38 | 0.0378 (17) | 0.0299 (16) | 0.0382 (17) | −0.0036 (13) | −0.0030 (14) | 0.0015 (13) |
C39 | 0.0357 (17) | 0.0293 (15) | 0.0278 (16) | 0.0021 (13) | −0.0011 (14) | −0.0025 (13) |
C40 | 0.0335 (15) | 0.0323 (16) | 0.0403 (17) | −0.0003 (12) | 0.0010 (14) | −0.0028 (14) |
O1 | 0.0428 (13) | 0.0256 (13) | 0.0584 (15) | −0.0023 (10) | 0.0090 (12) | −0.0049 (11) |
O2 | 0.0378 (11) | 0.0292 (12) | 0.0469 (14) | −0.0042 (9) | 0.0059 (10) | −0.0066 (11) |
O3 | 0.0386 (12) | 0.0240 (13) | 0.0519 (15) | 0.0005 (9) | 0.0078 (11) | −0.0032 (10) |
O4 | 0.0379 (12) | 0.0319 (12) | 0.0446 (14) | −0.0030 (9) | 0.0061 (10) | −0.0061 (10) |
C1—C6 | 1.398 (5) | C21—C26 | 1.387 (4) |
C1—C2 | 1.400 (4) | C21—C22 | 1.398 (4) |
C1—C7 | 1.463 (4) | C21—C27 | 1.466 (4) |
C2—C3 | 1.380 (4) | C22—C23 | 1.383 (4) |
C2—H2 | 0.9500 | C22—H22 | 0.9500 |
C3—C4 | 1.383 (4) | C23—C24 | 1.370 (5) |
C3—H3 | 0.9500 | C23—H23 | 0.9500 |
C4—C5 | 1.378 (5) | C24—C25 | 1.387 (4) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.394 (4) | C25—C26 | 1.387 (4) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—H6 | 0.9500 | C26—H26 | 0.9500 |
C7—C8 | 1.338 (4) | C27—C28 | 1.338 (4) |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C8—C20 | 1.487 (3) | C28—C29 | 1.488 (5) |
C8—C9 | 1.493 (5) | C28—C40 | 1.494 (4) |
C9—O1 | 1.233 (3) | C29—O3 | 1.237 (3) |
C9—C10 | 1.470 (4) | C29—C30 | 1.467 (4) |
C10—C19 | 1.388 (4) | C30—C39 | 1.391 (4) |
C10—C11 | 1.451 (5) | C30—C31 | 1.440 (5) |
C11—C12 | 1.416 (4) | C31—C32 | 1.412 (4) |
C11—C16 | 1.426 (4) | C31—C36 | 1.429 (5) |
C12—C13 | 1.368 (4) | C32—C33 | 1.372 (4) |
C12—H12 | 0.9500 | C32—H32 | 0.9500 |
C13—C14 | 1.396 (4) | C33—C34 | 1.406 (4) |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
C14—C15 | 1.368 (5) | C34—C35 | 1.350 (5) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.407 (4) | C35—C36 | 1.416 (4) |
C15—H15 | 0.9500 | C35—H35 | 0.9500 |
C16—C17 | 1.413 (4) | C36—C37 | 1.420 (4) |
C17—C18 | 1.352 (4) | C37—C38 | 1.357 (4) |
C17—H17 | 0.9500 | C37—H37 | 0.9500 |
C18—C19 | 1.415 (4) | C38—C39 | 1.412 (4) |
C18—H18 | 0.9500 | C38—H38 | 0.9500 |
C19—O2 | 1.346 (3) | C39—O4 | 1.354 (3) |
C20—O2 | 1.440 (3) | C40—O4 | 1.437 (3) |
C20—H20A | 0.9900 | C40—H40A | 0.9900 |
C20—H20B | 0.9900 | C40—H40B | 0.9900 |
C6—C1—C2 | 118.4 (3) | C26—C21—C27 | 117.9 (3) |
C6—C1—C7 | 123.1 (3) | C22—C21—C27 | 123.6 (3) |
C2—C1—C7 | 118.4 (3) | C23—C22—C21 | 120.4 (3) |
C3—C2—C1 | 120.8 (3) | C23—C22—H22 | 119.8 |
C3—C2—H2 | 119.6 | C21—C22—H22 | 119.8 |
C1—C2—H2 | 119.6 | C24—C23—C22 | 120.4 (3) |
C2—C3—C4 | 120.4 (3) | C24—C23—H23 | 119.8 |
C2—C3—H3 | 119.8 | C22—C23—H23 | 119.8 |
C4—C3—H3 | 119.8 | C23—C24—C25 | 120.4 (4) |
C5—C4—C3 | 119.6 (4) | C23—C24—H24 | 119.8 |
C5—C4—H4 | 120.2 | C25—C24—H24 | 119.8 |
C3—C4—H4 | 120.2 | C24—C25—C26 | 119.3 (3) |
C4—C5—C6 | 120.7 (3) | C24—C25—H25 | 120.4 |
C4—C5—H5 | 119.6 | C26—C25—H25 | 120.4 |
C6—C5—H5 | 119.6 | C25—C26—C21 | 121.1 (3) |
C5—C6—C1 | 120.0 (3) | C25—C26—H26 | 119.4 |
C5—C6—H6 | 120.0 | C21—C26—H26 | 119.4 |
C1—C6—H6 | 120.0 | C28—C27—C21 | 130.3 (3) |
C8—C7—C1 | 129.9 (3) | C28—C27—H27 | 114.8 |
C8—C7—H7 | 115.1 | C21—C27—H27 | 114.8 |
C1—C7—H7 | 115.1 | C27—C28—C29 | 118.1 (3) |
C7—C8—C20 | 125.0 (3) | C27—C28—C40 | 125.9 (3) |
C7—C8—C9 | 118.6 (2) | C29—C28—C40 | 115.9 (3) |
C20—C8—C9 | 116.5 (3) | O3—C29—C30 | 123.1 (3) |
O1—C9—C10 | 123.0 (3) | O3—C29—C28 | 120.6 (3) |
O1—C9—C8 | 120.7 (3) | C30—C29—C28 | 116.2 (3) |
C10—C9—C8 | 116.2 (3) | C39—C30—C31 | 117.8 (3) |
C19—C10—C11 | 117.8 (3) | C39—C30—C29 | 118.2 (3) |
C19—C10—C9 | 118.1 (3) | C31—C30—C29 | 123.5 (3) |
C11—C10—C9 | 123.7 (3) | C32—C31—C36 | 117.0 (3) |
C12—C11—C16 | 117.3 (3) | C32—C31—C30 | 123.7 (3) |
C12—C11—C10 | 123.8 (3) | C36—C31—C30 | 119.3 (3) |
C16—C11—C10 | 118.9 (3) | C33—C32—C31 | 121.1 (3) |
C13—C12—C11 | 121.6 (3) | C33—C32—H32 | 119.4 |
C13—C12—H12 | 119.2 | C31—C32—H32 | 119.4 |
C11—C12—H12 | 119.2 | C32—C33—C34 | 121.4 (3) |
C12—C13—C14 | 120.7 (3) | C32—C33—H33 | 119.3 |
C12—C13—H13 | 119.6 | C34—C33—H33 | 119.3 |
C14—C13—H13 | 119.6 | C35—C34—C33 | 119.1 (3) |
C15—C14—C13 | 119.4 (3) | C35—C34—H34 | 120.5 |
C15—C14—H14 | 120.3 | C33—C34—H34 | 120.5 |
C13—C14—H14 | 120.3 | C34—C35—C36 | 121.4 (3) |
C14—C15—C16 | 121.5 (3) | C34—C35—H35 | 119.3 |
C14—C15—H15 | 119.2 | C36—C35—H35 | 119.3 |
C16—C15—H15 | 119.2 | C35—C36—C37 | 120.7 (3) |
C15—C16—C17 | 120.7 (3) | C35—C36—C31 | 120.0 (3) |
C15—C16—C11 | 119.4 (3) | C37—C36—C31 | 119.3 (3) |
C17—C16—C11 | 119.9 (3) | C38—C37—C36 | 121.4 (3) |
C18—C17—C16 | 121.1 (3) | C38—C37—H37 | 119.3 |
C18—C17—H17 | 119.5 | C36—C37—H37 | 119.3 |
C16—C17—H17 | 119.5 | C37—C38—C39 | 119.3 (3) |
C17—C18—C19 | 120.0 (3) | C37—C38—H38 | 120.3 |
C17—C18—H18 | 120.0 | C39—C38—H38 | 120.3 |
C19—C18—H18 | 120.0 | O4—C39—C30 | 123.8 (3) |
O2—C19—C10 | 124.6 (3) | O4—C39—C38 | 113.4 (2) |
O2—C19—C18 | 113.0 (2) | C30—C39—C38 | 122.7 (3) |
C10—C19—C18 | 122.3 (3) | O4—C40—C28 | 112.3 (2) |
O2—C20—C8 | 112.7 (2) | O4—C40—H40A | 109.1 |
O2—C20—H20A | 109.1 | C28—C40—H40A | 109.1 |
C8—C20—H20A | 109.1 | O4—C40—H40B | 109.1 |
O2—C20—H20B | 109.1 | C28—C40—H40B | 109.1 |
C8—C20—H20B | 109.1 | H40A—C40—H40B | 107.9 |
H20A—C20—H20B | 107.8 | C19—O2—C20 | 116.7 (2) |
C26—C21—C22 | 118.4 (3) | C39—O4—C40 | 116.3 (2) |
C6—C1—C2—C3 | −1.6 (4) | C22—C23—C24—C25 | −0.9 (5) |
C7—C1—C2—C3 | 178.8 (3) | C23—C24—C25—C26 | 1.0 (5) |
C1—C2—C3—C4 | 0.1 (5) | C24—C25—C26—C21 | −1.8 (4) |
C2—C3—C4—C5 | 1.3 (5) | C22—C21—C26—C25 | 2.3 (4) |
C3—C4—C5—C6 | −1.2 (5) | C27—C21—C26—C25 | 179.9 (3) |
C4—C5—C6—C1 | −0.3 (5) | C26—C21—C27—C28 | 152.6 (3) |
C2—C1—C6—C5 | 1.7 (5) | C22—C21—C27—C28 | −30.0 (5) |
C7—C1—C6—C5 | −178.8 (3) | C21—C27—C28—C29 | 179.2 (3) |
C6—C1—C7—C8 | 32.2 (5) | C21—C27—C28—C40 | −0.7 (6) |
C2—C1—C7—C8 | −148.3 (4) | C27—C28—C29—O3 | −7.9 (5) |
C1—C7—C8—C20 | −0.2 (6) | C40—C28—C29—O3 | 172.0 (3) |
C1—C7—C8—C9 | 179.2 (3) | C27—C28—C29—C30 | 167.8 (3) |
C7—C8—C9—O1 | 9.3 (5) | C40—C28—C29—C30 | −12.3 (4) |
C20—C8—C9—O1 | −171.2 (3) | O3—C29—C30—C39 | 162.2 (3) |
C7—C8—C9—C10 | −166.3 (3) | C28—C29—C30—C39 | −13.4 (4) |
C20—C8—C9—C10 | 13.1 (4) | O3—C29—C30—C31 | −8.8 (5) |
O1—C9—C10—C19 | −165.1 (3) | C28—C29—C30—C31 | 175.6 (3) |
C8—C9—C10—C19 | 10.4 (4) | C39—C30—C31—C32 | 175.3 (3) |
O1—C9—C10—C11 | 7.2 (5) | C29—C30—C31—C32 | −13.7 (5) |
C8—C9—C10—C11 | −177.2 (3) | C39—C30—C31—C36 | −4.4 (5) |
C19—C10—C11—C12 | −177.7 (3) | C29—C30—C31—C36 | 166.6 (3) |
C9—C10—C11—C12 | 10.0 (5) | C36—C31—C32—C33 | −0.7 (5) |
C19—C10—C11—C16 | 1.9 (5) | C30—C31—C32—C33 | 179.6 (3) |
C9—C10—C11—C16 | −170.4 (3) | C31—C32—C33—C34 | −1.5 (5) |
C16—C11—C12—C13 | 0.0 (5) | C32—C33—C34—C35 | 2.5 (5) |
C10—C11—C12—C13 | 179.6 (3) | C33—C34—C35—C36 | −1.4 (5) |
C11—C12—C13—C14 | 1.4 (5) | C34—C35—C36—C37 | 179.5 (3) |
C12—C13—C14—C15 | −1.3 (5) | C34—C35—C36—C31 | −0.7 (5) |
C13—C14—C15—C16 | −0.1 (5) | C32—C31—C36—C35 | 1.7 (5) |
C14—C15—C16—C17 | 179.8 (3) | C30—C31—C36—C35 | −178.5 (3) |
C14—C15—C16—C11 | 1.5 (5) | C32—C31—C36—C37 | −178.5 (3) |
C12—C11—C16—C15 | −1.4 (5) | C30—C31—C36—C37 | 1.3 (5) |
C10—C11—C16—C15 | 179.0 (3) | C35—C36—C37—C38 | −178.6 (3) |
C12—C11—C16—C17 | −179.7 (3) | C31—C36—C37—C38 | 1.6 (4) |
C10—C11—C16—C17 | 0.7 (5) | C36—C37—C38—C39 | −1.3 (4) |
C15—C16—C17—C18 | 179.5 (3) | C31—C30—C39—O4 | −178.7 (3) |
C11—C16—C17—C18 | −2.2 (5) | C29—C30—C39—O4 | 9.8 (4) |
C16—C17—C18—C19 | 1.0 (4) | C31—C30—C39—C38 | 5.0 (4) |
C11—C10—C19—O2 | −179.9 (3) | C29—C30—C39—C38 | −166.5 (3) |
C9—C10—C19—O2 | −7.1 (4) | C37—C38—C39—O4 | −178.8 (3) |
C11—C10—C19—C18 | −3.2 (4) | C37—C38—C39—C30 | −2.1 (4) |
C9—C10—C19—C18 | 169.6 (3) | C27—C28—C40—O4 | −138.8 (3) |
C17—C18—C19—O2 | 178.8 (3) | C29—C28—C40—O4 | 41.4 (4) |
C17—C18—C19—C10 | 1.8 (4) | C10—C19—O2—C20 | −21.3 (4) |
C7—C8—C20—O2 | 139.9 (3) | C18—C19—O2—C20 | 161.7 (2) |
C9—C8—C20—O2 | −39.5 (4) | C8—C20—O2—C19 | 43.8 (4) |
C26—C21—C22—C23 | −2.2 (4) | C30—C39—O4—C40 | 21.4 (4) |
C27—C21—C22—C23 | −179.6 (3) | C38—C39—O4—C40 | −161.9 (2) |
C21—C22—C23—C24 | 1.5 (5) | C28—C40—O4—C39 | −46.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.95 | 2.38 | 2.770 (4) | 104 |
C12—H12···O1 | 0.95 | 2.22 | 2.856 (4) | 123 |
C27—H27···O3 | 0.95 | 2.35 | 2.755 (4) | 105 |
C32—H32···O3 | 0.95 | 2.25 | 2.857 (4) | 121 |
C20—H20A···Cg2i | 0.99 | 2.90 | 3.735 (3) | 143 |
C38—H38···Cg1 | 0.95 | 2.89 | 3.739 (3) | 149 |
Symmetry code: (i) x−1/2, −y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H14O2 |
Mr | 286.31 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 150 |
a, b, c (Å) | 12.3567 (6), 11.2675 (5), 20.4103 (12) |
V (Å3) | 2841.7 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.23 × 0.18 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.973, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33648, 2881, 2120 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.061, 0.94 |
No. of reflections | 2881 |
No. of parameters | 398 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.95 | 2.38 | 2.770 (4) | 104 |
C12—H12···O1 | 0.95 | 2.22 | 2.856 (4) | 123 |
C27—H27···O3 | 0.95 | 2.35 | 2.755 (4) | 105 |
C32—H32···O3 | 0.95 | 2.25 | 2.857 (4) | 121 |
C20—H20A···Cg2i | 0.99 | 2.90 | 3.735 (3) | 143 |
C38—H38···Cg1 | 0.95 | 2.89 | 3.739 (3) | 149 |
Symmetry code: (i) x−1/2, −y, z. |
The chromanone moiety present in the title compound consisting of the pyrone and benzene rings, 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 benzylidene chroman-4-ones, have identified as a potential source of new anti-fungal agents (Kang et al., 2004).
The geometric parameters in the title compound agree with the reported values of similar structure (Puviarasan et al., 1998; Wu et al., 2005a,b; Schollmeyer et al., 2005; Nissa et al., 2001). The dihedral angles between the phenyl ring and the benzene ring of chromanone unit in the two crystallographically independent molecules are 56.17 (4) and 55.62 (7)°.
The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π interactions.