organic compounds
The chalcone ethyl 2-[4-(2-{2,4-bis[(ethoxycarbonyl)methoxy]benzoyl}ethenyl)phenoxy]acetate
aSchool of Chemistry & Environmental Engineering, Jiujiang University, Jiujiang 332005, People's Republic of China
*Correspondence e-mail: caoxxyu@126.com
In the title molecule, C27H30O10, the benzene rings form a dihedral angle of 14.9 (2)°. The C=C bond is in an E conformation. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules, forming a three-dimensional network.
CCDC reference: 975718
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); 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: 975718
https://doi.org/10.1107/S1600536813033114/lh5675sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033114/lh5675Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033114/lh5675Isup3.cml
Isoliquiritigenin (2.56 g, 0.01 mol) and potassium hydroxide (2.45 g, 0.0438 mol) were dissolved in dry acetone (100 ml) in a three-neck flask. Then ethyl bromoacetate (6.93 g, 0.0415 mol) was dropwise added at room temperature and vigorously stirred for 3 h. The progress of the reaction was monitored by TCL (Si gel, developing solvent V (ethyl acetate) /V (benzene) = 1:2). After suction filtration and distilled to remove the solvent, a light yellow solid was obtained, 4.39 g, yield 85.4%. Recrystallization from ethanol produced light yellow needles.
All hydrogen atoms were placed in ideal positions with the C—H = 0.93 Å, C—H = 0.96 Å and C—H=0.97 Å with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmetyhl).
It has been determined in the authors lab that the title compound is a potential inhibitor of mushroom tyrosinase (results to be published soon) and the
determination of the title compound has been carried out to investigate its structure property relationships.In the title molecule (I, Fig. 1) the two benzene rings (C10-C15/C1-C6) form a dihedral angle of 14.9 (2)°. The C═C bond is in an E conformation. In the crystal, weak C—H···O hydrogen bonds connect molecules forming a three-dimensional network (Fig. 2). The structure of a related compound, (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one monohydrate, has been published previously (Wang et al., 2011).
For a related structure, see: Wang et al. (2011).
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).Fig. 1. View of a molecule of (I) showing displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. The crystal packing for (I), with weak C—H···O interactions shown as dashed lines. |
C27H30O10 | Z = 2 |
Mr = 514.51 | F(000) = 544 |
Triclinic, P1 | Dx = 1.319 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8225 (16) Å | Cell parameters from 2402 reflections |
b = 13.579 (3) Å | θ = 0.0–0.0° |
c = 13.780 (3) Å | µ = 0.10 mm−1 |
α = 63.004 (3)° | T = 298 K |
β = 87.157 (4)° | Block, light yellow |
γ = 83.377 (4)° | 0.12 × 0.10 × 0.10 mm |
V = 1295.6 (5) Å3 |
Bruker APEXII CCD diffractometer | 4538 independent reflections |
Radiation source: fine-focus sealed tube | 4137 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→9 |
Tmin = 0.988, Tmax = 0.990 | k = −16→16 |
16520 measured reflections | l = −16→16 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.0569P)2 + 1.0739P] where P = (Fo2 + 2Fc2)/3 |
4538 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C27H30O10 | γ = 83.377 (4)° |
Mr = 514.51 | V = 1295.6 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8225 (16) Å | Mo Kα radiation |
b = 13.579 (3) Å | µ = 0.10 mm−1 |
c = 13.780 (3) Å | T = 298 K |
α = 63.004 (3)° | 0.12 × 0.10 × 0.10 mm |
β = 87.157 (4)° |
Bruker APEXII CCD diffractometer | 4538 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4137 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.990 | Rint = 0.018 |
16520 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.20 | Δρmax = 0.39 e Å−3 |
4538 reflections | Δρmin = −0.23 e Å−3 |
337 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 | 0.7304 (4) | 0.4831 (2) | 0.6468 (2) | 0.0502 (7) | |
C2 | 0.7010 (4) | 0.5453 (2) | 0.7028 (2) | 0.0549 (8) | |
H2 | 0.7100 | 0.6213 | 0.6670 | 0.066* | |
C3 | 0.6586 (4) | 0.4962 (2) | 0.8106 (2) | 0.0532 (8) | |
H3 | 0.6387 | 0.5397 | 0.8471 | 0.064* | |
C4 | 0.6444 (4) | 0.3821 (2) | 0.8675 (2) | 0.0456 (7) | |
C5 | 0.6802 (4) | 0.3199 (2) | 0.8103 (2) | 0.0525 (7) | |
H5 | 0.6765 | 0.2434 | 0.8467 | 0.063* | |
C6 | 0.7211 (5) | 0.3687 (2) | 0.7015 (3) | 0.0570 (8) | |
H6 | 0.7423 | 0.3258 | 0.6646 | 0.068* | |
C7 | 0.5925 (4) | 0.3344 (2) | 0.9813 (2) | 0.0478 (7) | |
H7 | 0.5790 | 0.3829 | 1.0124 | 0.057* | |
C8 | 0.5619 (4) | 0.2298 (2) | 1.0465 (2) | 0.0467 (7) | |
H8 | 0.5751 | 0.1776 | 1.0197 | 0.056* | |
C9 | 0.5081 (4) | 0.1960 (2) | 1.1589 (2) | 0.0475 (7) | |
C10 | 0.4790 (4) | 0.0787 (2) | 1.2360 (2) | 0.0415 (6) | |
C11 | 0.3962 (4) | 0.0624 (2) | 1.3330 (2) | 0.0459 (7) | |
H11 | 0.3563 | 0.1246 | 1.3425 | 0.055* | |
C12 | 0.3700 (4) | −0.0400 (2) | 1.4151 (2) | 0.0485 (7) | |
H12 | 0.3136 | −0.0470 | 1.4786 | 0.058* | |
C13 | 0.4293 (4) | −0.1333 (2) | 1.4016 (2) | 0.0435 (6) | |
C14 | 0.5085 (4) | −0.1219 (2) | 1.3063 (2) | 0.0463 (7) | |
H14 | 0.5449 | −0.1848 | 1.2970 | 0.056* | |
C15 | 0.5343 (4) | −0.0178 (2) | 1.2239 (2) | 0.0432 (6) | |
C16 | 0.7769 (5) | 0.4821 (2) | 0.4757 (2) | 0.0587 (8) | |
H16A | 0.6704 | 0.4490 | 0.4833 | 0.070* | |
H16B | 0.8709 | 0.4230 | 0.5006 | 0.070* | |
C17 | 0.8034 (4) | 0.5619 (2) | 0.3588 (2) | 0.0517 (7) | |
C18 | 0.8388 (5) | 0.5709 (3) | 0.1834 (2) | 0.0623 (9) | |
H18A | 0.9452 | 0.6053 | 0.1695 | 0.075* | |
H18B | 0.7445 | 0.6287 | 0.1514 | 0.075* | |
C19 | 0.8467 (6) | 0.4911 (3) | 0.1360 (3) | 0.0855 (12) | |
H19A | 0.9402 | 0.4342 | 0.1687 | 0.128* | |
H19B | 0.8644 | 0.5300 | 0.0589 | 0.128* | |
H19C | 0.7405 | 0.4579 | 0.1501 | 0.128* | |
C20 | 0.3347 (4) | −0.2565 (3) | 1.5781 (2) | 0.0563 (8) | |
H20A | 0.3860 | −0.2134 | 1.6068 | 0.068* | |
H20B | 0.3559 | −0.3343 | 1.6303 | 0.068* | |
C21 | 0.1446 (5) | −0.2243 (2) | 1.5680 (2) | 0.0547 (8) | |
C22 | −0.0998 (5) | −0.1807 (3) | 1.4570 (4) | 0.0775 (11) | |
H22A | −0.1640 | −0.1962 | 1.5235 | 0.093* | |
H22B | −0.1500 | −0.2159 | 1.4194 | 0.093* | |
C23 | −0.1101 (6) | −0.0602 (3) | 1.3875 (4) | 0.0955 (14) | |
H23A | −0.0536 | −0.0262 | 1.4231 | 0.143* | |
H23B | −0.2287 | −0.0300 | 1.3748 | 0.143* | |
H23C | −0.0548 | −0.0455 | 1.3192 | 0.143* | |
C24 | 0.6858 (5) | −0.0966 (2) | 1.1165 (3) | 0.0592 (8) | |
H24A | 0.5934 | −0.1392 | 1.1180 | 0.071* | |
H24B | 0.7663 | −0.1441 | 1.1747 | 0.071* | |
C25 | 0.7749 (4) | −0.0555 (3) | 1.0089 (2) | 0.0522 (7) | |
C26 | 0.9388 (5) | −0.1206 (3) | 0.8969 (3) | 0.0672 (9) | |
H26A | 1.0458 | −0.0924 | 0.8998 | 0.081* | |
H26B | 0.8735 | −0.0652 | 0.8340 | 0.081* | |
C27 | 0.9746 (5) | −0.2257 (3) | 0.8881 (3) | 0.0744 (10) | |
H27A | 1.0383 | −0.2802 | 0.9509 | 0.112* | |
H27B | 1.0409 | −0.2128 | 0.8236 | 0.112* | |
H27C | 0.8680 | −0.2523 | 0.8839 | 0.112* | |
O1 | 0.4841 (4) | 0.26559 (18) | 1.19312 (19) | 0.0826 (9) | |
O2 | 0.7698 (3) | 0.54015 (16) | 0.53900 (17) | 0.0655 (7) | |
O3 | 0.8152 (4) | 0.65850 (18) | 0.32433 (19) | 0.0776 (8) | |
O4 | 0.8129 (3) | 0.50759 (17) | 0.29960 (16) | 0.0608 (6) | |
O5 | 0.4174 (3) | −0.24062 (16) | 1.47859 (16) | 0.0541 (5) | |
O6 | 0.0654 (4) | −0.2021 (3) | 1.6330 (2) | 0.0971 (10) | |
O7 | 0.0789 (3) | −0.22501 (18) | 1.48300 (19) | 0.0618 (6) | |
O8 | 0.6192 (3) | −0.00224 (16) | 1.13008 (17) | 0.0653 (7) | |
O9 | 0.7865 (4) | 0.03736 (19) | 0.9457 (2) | 0.0800 (8) | |
O10 | 0.8417 (3) | −0.14310 (17) | 0.99470 (18) | 0.0649 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0668 (19) | 0.0382 (15) | 0.0429 (15) | −0.0079 (13) | 0.0095 (13) | −0.0164 (13) |
C2 | 0.084 (2) | 0.0296 (14) | 0.0496 (17) | −0.0093 (14) | 0.0116 (15) | −0.0164 (13) |
C3 | 0.077 (2) | 0.0357 (15) | 0.0514 (17) | −0.0058 (14) | 0.0095 (15) | −0.0243 (14) |
C4 | 0.0550 (17) | 0.0351 (14) | 0.0448 (15) | −0.0043 (12) | 0.0028 (13) | −0.0167 (12) |
C5 | 0.077 (2) | 0.0294 (14) | 0.0467 (16) | −0.0097 (13) | 0.0093 (14) | −0.0137 (12) |
C6 | 0.087 (2) | 0.0378 (15) | 0.0510 (17) | −0.0099 (15) | 0.0129 (16) | −0.0245 (14) |
C7 | 0.0630 (18) | 0.0347 (14) | 0.0464 (16) | −0.0035 (13) | 0.0047 (13) | −0.0198 (13) |
C8 | 0.0611 (18) | 0.0381 (15) | 0.0424 (15) | −0.0054 (13) | 0.0022 (13) | −0.0195 (12) |
C9 | 0.0638 (19) | 0.0367 (14) | 0.0436 (15) | −0.0035 (13) | 0.0021 (13) | −0.0202 (13) |
C10 | 0.0482 (16) | 0.0381 (14) | 0.0398 (14) | −0.0039 (11) | 0.0011 (12) | −0.0191 (12) |
C11 | 0.0592 (18) | 0.0397 (15) | 0.0457 (15) | −0.0066 (13) | 0.0067 (13) | −0.0257 (13) |
C12 | 0.0607 (18) | 0.0477 (16) | 0.0422 (15) | −0.0140 (13) | 0.0145 (13) | −0.0242 (13) |
C13 | 0.0474 (16) | 0.0383 (14) | 0.0421 (15) | −0.0092 (12) | 0.0025 (12) | −0.0150 (12) |
C14 | 0.0580 (18) | 0.0355 (14) | 0.0486 (16) | −0.0049 (12) | 0.0045 (13) | −0.0222 (13) |
C15 | 0.0545 (17) | 0.0392 (14) | 0.0379 (14) | −0.0053 (12) | 0.0060 (12) | −0.0196 (12) |
C16 | 0.088 (2) | 0.0410 (16) | 0.0473 (17) | −0.0109 (15) | 0.0127 (16) | −0.0206 (14) |
C17 | 0.067 (2) | 0.0381 (16) | 0.0475 (16) | −0.0028 (13) | 0.0083 (14) | −0.0183 (13) |
C18 | 0.085 (2) | 0.0570 (19) | 0.0402 (16) | −0.0134 (17) | 0.0100 (15) | −0.0179 (15) |
C19 | 0.126 (4) | 0.080 (3) | 0.057 (2) | −0.022 (2) | 0.017 (2) | −0.037 (2) |
C20 | 0.077 (2) | 0.0471 (17) | 0.0390 (15) | −0.0150 (15) | 0.0043 (15) | −0.0130 (13) |
C21 | 0.079 (2) | 0.0411 (16) | 0.0405 (16) | −0.0178 (15) | 0.0179 (15) | −0.0143 (13) |
C22 | 0.066 (2) | 0.069 (2) | 0.105 (3) | −0.0102 (18) | −0.001 (2) | −0.045 (2) |
C23 | 0.076 (3) | 0.072 (3) | 0.122 (4) | −0.001 (2) | −0.025 (3) | −0.028 (3) |
C24 | 0.086 (2) | 0.0410 (16) | 0.0536 (18) | −0.0068 (15) | 0.0161 (16) | −0.0254 (14) |
C25 | 0.070 (2) | 0.0463 (17) | 0.0440 (16) | −0.0119 (14) | 0.0091 (14) | −0.0231 (14) |
C26 | 0.071 (2) | 0.081 (2) | 0.063 (2) | −0.0145 (18) | 0.0210 (17) | −0.0441 (19) |
C27 | 0.080 (3) | 0.085 (3) | 0.071 (2) | 0.000 (2) | 0.0112 (19) | −0.049 (2) |
O1 | 0.149 (3) | 0.0424 (12) | 0.0593 (14) | −0.0150 (14) | 0.0280 (15) | −0.0274 (11) |
O2 | 0.1146 (19) | 0.0361 (11) | 0.0445 (12) | −0.0161 (11) | 0.0222 (12) | −0.0174 (9) |
O3 | 0.133 (2) | 0.0401 (13) | 0.0555 (14) | −0.0114 (13) | 0.0162 (14) | −0.0190 (11) |
O4 | 0.0943 (17) | 0.0451 (12) | 0.0437 (11) | −0.0165 (11) | 0.0133 (11) | −0.0197 (10) |
O5 | 0.0667 (14) | 0.0383 (11) | 0.0483 (12) | −0.0082 (9) | 0.0106 (10) | −0.0121 (9) |
O6 | 0.114 (2) | 0.114 (2) | 0.0670 (17) | −0.0088 (18) | 0.0327 (16) | −0.0479 (17) |
O7 | 0.0630 (14) | 0.0582 (13) | 0.0735 (15) | −0.0026 (11) | −0.0009 (11) | −0.0387 (12) |
O8 | 0.1049 (18) | 0.0377 (11) | 0.0509 (12) | −0.0062 (11) | 0.0263 (12) | −0.0208 (10) |
O9 | 0.124 (2) | 0.0459 (14) | 0.0626 (15) | −0.0082 (13) | 0.0233 (15) | −0.0203 (12) |
O10 | 0.0907 (17) | 0.0486 (12) | 0.0585 (13) | −0.0094 (11) | 0.0247 (12) | −0.0288 (11) |
C1—O2 | 1.366 (3) | C17—O4 | 1.319 (4) |
C1—C2 | 1.375 (4) | C18—O4 | 1.450 (4) |
C1—C6 | 1.394 (4) | C18—C19 | 1.492 (5) |
C2—C3 | 1.365 (4) | C18—H18A | 0.9700 |
C2—H2 | 0.9300 | C18—H18B | 0.9700 |
C3—C4 | 1.399 (4) | C19—H19A | 0.9600 |
C3—H3 | 0.9300 | C19—H19B | 0.9600 |
C4—C5 | 1.393 (4) | C19—H19C | 0.9600 |
C4—C7 | 1.455 (4) | C20—O5 | 1.422 (4) |
C5—C6 | 1.375 (4) | C20—C21 | 1.496 (5) |
C5—H5 | 0.9300 | C20—H20A | 0.9700 |
C6—H6 | 0.9300 | C20—H20B | 0.9700 |
C7—C8 | 1.335 (4) | C21—O6 | 1.193 (4) |
C7—H7 | 0.9300 | C21—O7 | 1.307 (4) |
C8—C9 | 1.457 (4) | C22—O7 | 1.451 (4) |
C8—H8 | 0.9300 | C22—C23 | 1.468 (5) |
C9—O1 | 1.227 (3) | C22—H22A | 0.9700 |
C9—C10 | 1.497 (4) | C22—H22B | 0.9700 |
C10—C11 | 1.389 (4) | C23—H23A | 0.9600 |
C10—C15 | 1.412 (4) | C23—H23B | 0.9600 |
C11—C12 | 1.368 (4) | C23—H23C | 0.9600 |
C11—H11 | 0.9300 | C24—O8 | 1.415 (3) |
C12—C13 | 1.387 (4) | C24—C25 | 1.494 (4) |
C12—H12 | 0.9300 | C24—H24A | 0.9700 |
C13—O5 | 1.370 (3) | C24—H24B | 0.9700 |
C13—C14 | 1.375 (4) | C25—O9 | 1.174 (4) |
C14—C15 | 1.384 (4) | C25—O10 | 1.335 (4) |
C14—H14 | 0.9300 | C26—O10 | 1.437 (4) |
C15—O8 | 1.363 (3) | C26—C27 | 1.481 (5) |
C16—O2 | 1.412 (3) | C26—H26A | 0.9700 |
C16—C17 | 1.499 (4) | C26—H26B | 0.9700 |
C16—H16A | 0.9700 | C27—H27A | 0.9600 |
C16—H16B | 0.9700 | C27—H27B | 0.9600 |
C17—O3 | 1.189 (3) | C27—H27C | 0.9600 |
O2—C1—C2 | 116.0 (2) | O4—C18—H18B | 110.3 |
O2—C1—C6 | 124.5 (3) | C19—C18—H18B | 110.3 |
C2—C1—C6 | 119.5 (3) | H18A—C18—H18B | 108.6 |
C3—C2—C1 | 120.5 (3) | C18—C19—H19A | 109.5 |
C3—C2—H2 | 119.8 | C18—C19—H19B | 109.5 |
C1—C2—H2 | 119.8 | H19A—C19—H19B | 109.5 |
C2—C3—C4 | 121.5 (3) | C18—C19—H19C | 109.5 |
C2—C3—H3 | 119.2 | H19A—C19—H19C | 109.5 |
C4—C3—H3 | 119.2 | H19B—C19—H19C | 109.5 |
C5—C4—C3 | 117.1 (3) | O5—C20—C21 | 114.2 (3) |
C5—C4—C7 | 123.4 (2) | O5—C20—H20A | 108.7 |
C3—C4—C7 | 119.5 (2) | C21—C20—H20A | 108.7 |
C6—C5—C4 | 121.7 (3) | O5—C20—H20B | 108.7 |
C6—C5—H5 | 119.1 | C21—C20—H20B | 108.7 |
C4—C5—H5 | 119.1 | H20A—C20—H20B | 107.6 |
C5—C6—C1 | 119.6 (3) | O6—C21—O7 | 125.4 (4) |
C5—C6—H6 | 120.2 | O6—C21—C20 | 121.9 (3) |
C1—C6—H6 | 120.2 | O7—C21—C20 | 112.7 (3) |
C8—C7—C4 | 128.1 (3) | O7—C22—C23 | 109.5 (3) |
C8—C7—H7 | 116.0 | O7—C22—H22A | 109.8 |
C4—C7—H7 | 116.0 | C23—C22—H22A | 109.8 |
C7—C8—C9 | 121.0 (3) | O7—C22—H22B | 109.8 |
C7—C8—H8 | 119.5 | C23—C22—H22B | 109.8 |
C9—C8—H8 | 119.5 | H22A—C22—H22B | 108.2 |
O1—C9—C8 | 119.6 (3) | C22—C23—H23A | 109.5 |
O1—C9—C10 | 117.6 (3) | C22—C23—H23B | 109.5 |
C8—C9—C10 | 122.8 (2) | H23A—C23—H23B | 109.5 |
C11—C10—C15 | 116.3 (2) | C22—C23—H23C | 109.5 |
C11—C10—C9 | 116.4 (2) | H23A—C23—H23C | 109.5 |
C15—C10—C9 | 127.2 (2) | H23B—C23—H23C | 109.5 |
C12—C11—C10 | 123.8 (3) | O8—C24—C25 | 107.2 (2) |
C12—C11—H11 | 118.1 | O8—C24—H24A | 110.3 |
C10—C11—H11 | 118.1 | C25—C24—H24A | 110.3 |
C11—C12—C13 | 118.5 (3) | O8—C24—H24B | 110.3 |
C11—C12—H12 | 120.7 | C25—C24—H24B | 110.3 |
C13—C12—H12 | 120.7 | H24A—C24—H24B | 108.5 |
O5—C13—C14 | 115.1 (2) | O9—C25—O10 | 124.3 (3) |
O5—C13—C12 | 124.6 (2) | O9—C25—C24 | 127.2 (3) |
C14—C13—C12 | 120.2 (2) | O10—C25—C24 | 108.5 (2) |
C13—C14—C15 | 120.6 (2) | O10—C26—C27 | 108.1 (3) |
C13—C14—H14 | 119.7 | O10—C26—H26A | 110.1 |
C15—C14—H14 | 119.7 | C27—C26—H26A | 110.1 |
O8—C15—C14 | 122.9 (2) | O10—C26—H26B | 110.1 |
O8—C15—C10 | 116.4 (2) | C27—C26—H26B | 110.1 |
C14—C15—C10 | 120.6 (2) | H26A—C26—H26B | 108.4 |
O2—C16—C17 | 108.9 (2) | C26—C27—H27A | 109.5 |
O2—C16—H16A | 109.9 | C26—C27—H27B | 109.5 |
C17—C16—H16A | 109.9 | H27A—C27—H27B | 109.5 |
O2—C16—H16B | 109.9 | C26—C27—H27C | 109.5 |
C17—C16—H16B | 109.9 | H27A—C27—H27C | 109.5 |
H16A—C16—H16B | 108.3 | H27B—C27—H27C | 109.5 |
O3—C17—O4 | 125.1 (3) | C1—O2—C16 | 117.3 (2) |
O3—C17—C16 | 125.8 (3) | C17—O4—C18 | 117.4 (2) |
O4—C17—C16 | 109.1 (2) | C13—O5—C20 | 117.2 (2) |
O4—C18—C19 | 106.9 (3) | C21—O7—C22 | 117.3 (3) |
O4—C18—H18A | 110.3 | C15—O8—C24 | 118.7 (2) |
C19—C18—H18A | 110.3 | C25—O10—C26 | 116.9 (3) |
O2—C1—C2—C3 | 179.2 (3) | C11—C10—C15—O8 | −178.5 (3) |
C6—C1—C2—C3 | −1.7 (5) | C9—C10—C15—O8 | −2.1 (4) |
C1—C2—C3—C4 | 0.3 (5) | C11—C10—C15—C14 | −1.1 (4) |
C2—C3—C4—C5 | 1.8 (5) | C9—C10—C15—C14 | 175.2 (3) |
C2—C3—C4—C7 | −177.7 (3) | O2—C16—C17—O3 | −0.6 (5) |
C3—C4—C5—C6 | −2.6 (5) | O2—C16—C17—O4 | 179.0 (3) |
C7—C4—C5—C6 | 176.9 (3) | O5—C20—C21—O6 | −158.1 (3) |
C4—C5—C6—C1 | 1.3 (5) | O5—C20—C21—O7 | 22.8 (4) |
O2—C1—C6—C5 | 180.0 (3) | O8—C24—C25—O9 | −1.1 (5) |
C2—C1—C6—C5 | 0.9 (5) | O8—C24—C25—O10 | 179.0 (3) |
C5—C4—C7—C8 | −3.9 (5) | C2—C1—O2—C16 | −171.3 (3) |
C3—C4—C7—C8 | 175.5 (3) | C6—C1—O2—C16 | 9.6 (5) |
C4—C7—C8—C9 | −179.1 (3) | C17—C16—O2—C1 | 174.2 (3) |
C7—C8—C9—O1 | 2.8 (5) | O3—C17—O4—C18 | −0.3 (5) |
C7—C8—C9—C10 | −177.6 (3) | C16—C17—O4—C18 | −179.9 (3) |
O1—C9—C10—C11 | 11.9 (4) | C19—C18—O4—C17 | 179.4 (3) |
C8—C9—C10—C11 | −167.7 (3) | C14—C13—O5—C20 | −179.2 (3) |
O1—C9—C10—C15 | −164.5 (3) | C12—C13—O5—C20 | 1.5 (4) |
C8—C9—C10—C15 | 15.9 (5) | C21—C20—O5—C13 | 70.3 (3) |
C15—C10—C11—C12 | 1.3 (4) | O6—C21—O7—C22 | 9.1 (5) |
C9—C10—C11—C12 | −175.5 (3) | C20—C21—O7—C22 | −171.9 (3) |
C10—C11—C12—C13 | 0.1 (5) | C23—C22—O7—C21 | 87.1 (4) |
C11—C12—C13—O5 | 177.5 (3) | C14—C15—O8—C24 | −0.8 (5) |
C11—C12—C13—C14 | −1.7 (4) | C10—C15—O8—C24 | 176.5 (3) |
O5—C13—C14—C15 | −177.4 (3) | C25—C24—O8—C15 | −178.7 (3) |
C12—C13—C14—C15 | 1.9 (4) | O9—C25—O10—C26 | 2.3 (5) |
C13—C14—C15—O8 | 176.8 (3) | C24—C25—O10—C26 | −177.7 (3) |
C13—C14—C15—C10 | −0.4 (4) | C27—C26—O10—C25 | −170.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.52 | 3.276 (4) | 138 |
C16—H16B···O7ii | 0.97 | 2.58 | 3.337 (4) | 135 |
C20—H20B···O4ii | 0.97 | 2.60 | 3.360 (4) | 136 |
C24—H24B···O3iii | 0.97 | 2.53 | 3.339 (4) | 141 |
C27—H27B···O6iv | 0.96 | 2.56 | 3.426 (4) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2; (iii) x, y−1, z+1; (iv) x+1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.52 | 3.276 (4) | 138.4 |
C16—H16B···O7ii | 0.97 | 2.58 | 3.337 (4) | 135.1 |
C20—H20B···O4ii | 0.97 | 2.60 | 3.360 (4) | 135.7 |
C24—H24B···O3iii | 0.97 | 2.53 | 3.339 (4) | 140.6 |
C27—H27B···O6iv | 0.96 | 2.56 | 3.426 (4) | 149.8 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2; (iii) x, y−1, z+1; (iv) x+1, y, z−1. |
Acknowledgements
This study was funded by Jiangxi Provincial Department of Education (KJLD12047) and Jiangxi Provincial Department of Science and Technology (20132BBE50021).
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It has been determined in the authors lab that the title compound is a potential inhibitor of mushroom tyrosinase (results to be published soon) and the crystal structure determination of the title compound has been carried out to investigate its structure property relationships.
In the title molecule (I, Fig. 1) the two benzene rings (C10-C15/C1-C6) form a dihedral angle of 14.9 (2)°. The C═C bond is in an E conformation. In the crystal, weak C—H···O hydrogen bonds connect molecules forming a three-dimensional network (Fig. 2). The structure of a related compound, (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one monohydrate, has been published previously (Wang et al., 2011).