organic compounds
(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
aInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China, bSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, cLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and dSchool of Pharmacy, Hainan Medical College, Haikou, Hainan Province 571101, People's Republic of China
*Correspondence e-mail: wjzwzmc@126.com
In the title chalcone derivative, C20H22O6, the dihedral angle between the mean planes of the benzene rings is 15.77 (6)°. The H atoms of the central C=C double bond are in a trans configuration. There are a number of C—H⋯O interactions and a C—H⋯π interaction present in the crystal structure.
Related literature
For related structures, see: Wu et al. (2010, 2011); Huang et al. (2010); Peng et al. (2010). For applications of see: Wu et al. (2010, 2011); Nielsen et al. (2005). For the hydrogen-bond analysis, see: Spek (2009).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811053001/zq2146sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811053001/zq2146Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811053001/zq2146Isup3.cml
The title compound was synthesized by Claisen-Schmidt condensation between 2,4-dimethoxybenzaldehyde and 1-(3,4,5-trimethoxyphenyl)ethanone. 2,4-Dimethoxybenzaldehyde (1 mmol) and 1-(3,4,5-trimethoxyphenyl)ethanone (1 mmol) were dissolved in ehanol (20 ml). The reaction temperature was controlled at 283 K, and then NaOH (20%, 3 drops) was added. The reaction was monitored by
20 ml H2O was added 5 h later and the yellow solid precipitated. It was washed with a mixture of water and cold ethanol, and dried (yield: 70%; mp 125.7–127.7°C). Single crystals of the title compound were obtained by recrystallization from a solution of CH3CH2OH / CH2Cl2 at 293 K.All H atoms were placed in geometrical positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. Crystal packing of the title compound viewed down the a axis. |
C20H22O6 | F(000) = 760 |
Mr = 358.38 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2728 reflections |
a = 8.3111 (11) Å | θ = 5.2–49.2° |
b = 13.8493 (17) Å | µ = 0.10 mm−1 |
c = 15.887 (2) Å | T = 293 K |
β = 101.588 (2)° | Prismatic, green |
V = 1791.4 (4) Å3 | 0.40 × 0.37 × 0.31 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 3512 independent reflections |
Radiation source: fine-focus sealed tube | 2452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
phi and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→9 |
Tmin = 0.651, Tmax = 1.000 | k = −17→15 |
9663 measured reflections | l = −16→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
3512 reflections | Δρmax = 0.20 e Å−3 |
241 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0069 (15) |
C20H22O6 | V = 1791.4 (4) Å3 |
Mr = 358.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3111 (11) Å | µ = 0.10 mm−1 |
b = 13.8493 (17) Å | T = 293 K |
c = 15.887 (2) Å | 0.40 × 0.37 × 0.31 mm |
β = 101.588 (2)° |
Bruker SMART CCD diffractometer | 3512 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2452 reflections with I > 2σ(I) |
Tmin = 0.651, Tmax = 1.000 | Rint = 0.045 |
9663 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.20 e Å−3 |
3512 reflections | Δρmin = −0.19 e Å−3 |
241 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 | 0.3078 (3) | 0.60842 (10) | −0.03257 (9) | 0.0969 (7) | |
O2 | 0.45908 (16) | 0.73756 (8) | 0.24726 (7) | 0.0510 (4) | |
O3 | 0.34229 (18) | 0.58134 (9) | 0.49898 (7) | 0.0629 (4) | |
O4 | 0.20538 (17) | 0.38935 (8) | −0.28996 (7) | 0.0549 (4) | |
O5 | 0.11723 (15) | 0.21987 (8) | −0.23292 (7) | 0.0487 (3) | |
O6 | 0.07241 (18) | 0.19802 (8) | −0.07336 (8) | 0.0614 (4) | |
C1 | 0.2622 (3) | 0.53394 (12) | −0.00427 (11) | 0.0532 (5) | |
C2 | 0.2513 (2) | 0.52558 (12) | 0.08616 (11) | 0.0494 (5) | |
H2 | 0.1994 | 0.4719 | 0.1037 | 0.059* | |
C3 | 0.3124 (2) | 0.59147 (12) | 0.14391 (11) | 0.0478 (5) | |
H3 | 0.3597 | 0.6450 | 0.1231 | 0.057* | |
C4 | 0.3155 (2) | 0.59116 (11) | 0.23532 (10) | 0.0397 (4) | |
C5 | 0.3969 (2) | 0.66447 (11) | 0.28813 (10) | 0.0395 (4) | |
C6 | 0.4097 (2) | 0.66259 (11) | 0.37629 (10) | 0.0438 (4) | |
H6 | 0.4670 | 0.7109 | 0.4104 | 0.053* | |
C7 | 0.3368 (2) | 0.58853 (12) | 0.41331 (11) | 0.0454 (4) | |
C8 | 0.2505 (2) | 0.51675 (12) | 0.36245 (12) | 0.0495 (5) | |
H8 | 0.1993 | 0.4677 | 0.3872 | 0.059* | |
C9 | 0.2416 (2) | 0.51894 (11) | 0.27580 (11) | 0.0456 (5) | |
H9 | 0.1839 | 0.4703 | 0.2423 | 0.055* | |
C10 | 0.2178 (2) | 0.44929 (11) | −0.06312 (10) | 0.0441 (5) | |
C11 | 0.2324 (2) | 0.46042 (11) | −0.14787 (11) | 0.0451 (4) | |
H11 | 0.2675 | 0.5192 | −0.1662 | 0.054* | |
C12 | 0.1956 (2) | 0.38529 (11) | −0.20524 (10) | 0.0428 (4) | |
C13 | 0.1453 (2) | 0.29723 (11) | −0.17775 (10) | 0.0407 (4) | |
C14 | 0.1279 (2) | 0.28626 (11) | −0.09326 (11) | 0.0436 (4) | |
C15 | 0.1647 (2) | 0.36210 (11) | −0.03595 (11) | 0.0468 (5) | |
H15 | 0.1538 | 0.3545 | 0.0208 | 0.056* | |
C16 | 0.4271 (3) | 0.65505 (15) | 0.55295 (12) | 0.0817 (8) | |
H16A | 0.5415 | 0.6534 | 0.5505 | 0.123* | |
H16B | 0.4147 | 0.6445 | 0.6110 | 0.123* | |
H16C | 0.3821 | 0.7169 | 0.5336 | 0.123* | |
C17 | 0.5458 (2) | 0.81254 (12) | 0.29860 (11) | 0.0517 (5) | |
H17A | 0.4751 | 0.8421 | 0.3321 | 0.078* | |
H17B | 0.5805 | 0.8601 | 0.2621 | 0.078* | |
H17C | 0.6402 | 0.7859 | 0.3363 | 0.078* | |
C18 | 0.2455 (3) | 0.47971 (13) | −0.32250 (12) | 0.0632 (6) | |
H18A | 0.1629 | 0.5263 | −0.3168 | 0.095* | |
H18B | 0.2508 | 0.4730 | −0.3820 | 0.095* | |
H18C | 0.3501 | 0.5010 | −0.2907 | 0.095* | |
C19 | −0.0442 (2) | 0.21605 (14) | −0.28238 (13) | 0.0635 (6) | |
H19A | −0.1204 | 0.2052 | −0.2452 | 0.095* | |
H19B | −0.0523 | 0.1643 | −0.3232 | 0.095* | |
H19C | −0.0697 | 0.2761 | −0.3123 | 0.095* | |
C20 | 0.0313 (3) | 0.18677 (15) | 0.00746 (13) | 0.0796 (7) | |
H20A | 0.1280 | 0.1943 | 0.0515 | 0.119* | |
H20B | −0.0141 | 0.1236 | 0.0115 | 0.119* | |
H20C | −0.0483 | 0.2347 | 0.0147 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.196 (2) | 0.0472 (8) | 0.0459 (9) | −0.0398 (10) | 0.0199 (10) | −0.0057 (6) |
O2 | 0.0720 (9) | 0.0430 (7) | 0.0373 (7) | −0.0161 (6) | 0.0091 (6) | −0.0008 (5) |
O3 | 0.1002 (12) | 0.0532 (8) | 0.0383 (7) | −0.0019 (7) | 0.0214 (7) | 0.0041 (6) |
O4 | 0.0851 (10) | 0.0457 (7) | 0.0366 (7) | −0.0065 (6) | 0.0188 (6) | −0.0026 (5) |
O5 | 0.0564 (8) | 0.0391 (6) | 0.0498 (7) | 0.0031 (6) | 0.0088 (6) | −0.0121 (5) |
O6 | 0.0974 (11) | 0.0389 (7) | 0.0520 (8) | −0.0099 (7) | 0.0252 (7) | −0.0010 (6) |
C1 | 0.0786 (14) | 0.0389 (10) | 0.0384 (10) | −0.0011 (9) | 0.0028 (9) | −0.0016 (8) |
C2 | 0.0649 (13) | 0.0396 (9) | 0.0429 (10) | −0.0037 (9) | 0.0092 (9) | −0.0034 (8) |
C3 | 0.0658 (13) | 0.0363 (9) | 0.0400 (10) | −0.0048 (8) | 0.0076 (8) | −0.0006 (7) |
C4 | 0.0486 (11) | 0.0334 (8) | 0.0364 (9) | 0.0030 (7) | 0.0067 (8) | −0.0017 (7) |
C5 | 0.0473 (10) | 0.0338 (8) | 0.0375 (9) | −0.0002 (7) | 0.0087 (8) | 0.0010 (7) |
C6 | 0.0574 (12) | 0.0376 (9) | 0.0353 (9) | −0.0013 (8) | 0.0065 (8) | −0.0034 (7) |
C7 | 0.0625 (12) | 0.0395 (9) | 0.0361 (10) | 0.0095 (8) | 0.0141 (8) | 0.0039 (7) |
C8 | 0.0659 (13) | 0.0354 (9) | 0.0514 (11) | −0.0025 (8) | 0.0217 (9) | 0.0041 (8) |
C9 | 0.0551 (12) | 0.0338 (9) | 0.0484 (11) | −0.0019 (8) | 0.0119 (9) | −0.0064 (7) |
C10 | 0.0560 (12) | 0.0377 (9) | 0.0353 (9) | 0.0018 (8) | 0.0018 (8) | −0.0013 (7) |
C11 | 0.0581 (12) | 0.0353 (9) | 0.0410 (10) | −0.0034 (8) | 0.0078 (8) | 0.0011 (7) |
C12 | 0.0520 (11) | 0.0412 (9) | 0.0354 (9) | 0.0038 (8) | 0.0094 (8) | −0.0016 (7) |
C13 | 0.0466 (11) | 0.0343 (9) | 0.0402 (10) | 0.0047 (7) | 0.0066 (8) | −0.0052 (7) |
C14 | 0.0537 (11) | 0.0328 (9) | 0.0440 (10) | 0.0007 (8) | 0.0086 (8) | 0.0008 (7) |
C15 | 0.0641 (13) | 0.0422 (10) | 0.0334 (9) | 0.0020 (9) | 0.0082 (8) | 0.0010 (7) |
C16 | 0.138 (2) | 0.0694 (14) | 0.0348 (11) | −0.0064 (14) | 0.0103 (12) | −0.0023 (10) |
C17 | 0.0619 (13) | 0.0421 (10) | 0.0515 (11) | −0.0131 (9) | 0.0125 (9) | −0.0037 (8) |
C18 | 0.0934 (17) | 0.0537 (12) | 0.0456 (11) | −0.0055 (11) | 0.0211 (11) | 0.0058 (9) |
C19 | 0.0649 (14) | 0.0589 (12) | 0.0627 (13) | −0.0058 (10) | 0.0032 (10) | −0.0159 (10) |
C20 | 0.117 (2) | 0.0644 (14) | 0.0642 (14) | −0.0289 (14) | 0.0338 (13) | 0.0030 (11) |
O1—C1 | 1.216 (2) | C9—H9 | 0.9300 |
O2—C5 | 1.3595 (19) | C10—C15 | 1.384 (2) |
O2—C17 | 1.4235 (18) | C10—C11 | 1.385 (2) |
O3—C7 | 1.3564 (19) | C11—C12 | 1.377 (2) |
O3—C16 | 1.425 (2) | C11—H11 | 0.9300 |
O4—C12 | 1.366 (2) | C12—C13 | 1.388 (2) |
O4—C18 | 1.419 (2) | C13—C14 | 1.387 (2) |
O5—C13 | 1.3742 (18) | C14—C15 | 1.383 (2) |
O5—C19 | 1.413 (2) | C15—H15 | 0.9300 |
O6—C14 | 1.3656 (19) | C16—H16A | 0.9600 |
O6—C20 | 1.402 (2) | C16—H16B | 0.9600 |
C1—C2 | 1.462 (2) | C16—H16C | 0.9600 |
C1—C10 | 1.499 (2) | C17—H17A | 0.9600 |
C2—C3 | 1.321 (2) | C17—H17B | 0.9600 |
C2—H2 | 0.9300 | C17—H17C | 0.9600 |
C3—C4 | 1.447 (2) | C18—H18A | 0.9600 |
C3—H3 | 0.9300 | C18—H18B | 0.9600 |
C4—C9 | 1.396 (2) | C18—H18C | 0.9600 |
C4—C5 | 1.402 (2) | C19—H19A | 0.9600 |
C5—C6 | 1.383 (2) | C19—H19B | 0.9600 |
C6—C7 | 1.381 (2) | C19—H19C | 0.9600 |
C6—H6 | 0.9300 | C20—H20A | 0.9600 |
C7—C8 | 1.387 (2) | C20—H20B | 0.9600 |
C8—C9 | 1.364 (2) | C20—H20C | 0.9600 |
C8—H8 | 0.9300 | ||
C5—O2—C17 | 117.82 (13) | C11—C12—C13 | 119.79 (16) |
C7—O3—C16 | 117.64 (15) | O5—C13—C14 | 119.64 (14) |
C12—O4—C18 | 117.40 (13) | O5—C13—C12 | 120.52 (15) |
C13—O5—C19 | 113.86 (13) | C14—C13—C12 | 119.82 (14) |
C14—O6—C20 | 117.86 (14) | O6—C14—C15 | 124.57 (16) |
O1—C1—C2 | 121.06 (15) | O6—C14—C13 | 115.33 (14) |
O1—C1—C10 | 119.26 (16) | C15—C14—C13 | 120.10 (15) |
C2—C1—C10 | 119.67 (15) | C14—C15—C10 | 119.96 (16) |
C3—C2—C1 | 122.45 (17) | C14—C15—H15 | 120.0 |
C3—C2—H2 | 118.8 | C10—C15—H15 | 120.0 |
C1—C2—H2 | 118.8 | O3—C16—H16A | 109.5 |
C2—C3—C4 | 128.42 (17) | O3—C16—H16B | 109.5 |
C2—C3—H3 | 115.8 | H16A—C16—H16B | 109.5 |
C4—C3—H3 | 115.8 | O3—C16—H16C | 109.5 |
C9—C4—C5 | 116.56 (15) | H16A—C16—H16C | 109.5 |
C9—C4—C3 | 122.93 (14) | H16B—C16—H16C | 109.5 |
C5—C4—C3 | 120.50 (15) | O2—C17—H17A | 109.5 |
O2—C5—C6 | 122.56 (14) | O2—C17—H17B | 109.5 |
O2—C5—C4 | 115.95 (14) | H17A—C17—H17B | 109.5 |
C6—C5—C4 | 121.48 (15) | O2—C17—H17C | 109.5 |
C7—C6—C5 | 119.61 (15) | H17A—C17—H17C | 109.5 |
C7—C6—H6 | 120.2 | H17B—C17—H17C | 109.5 |
C5—C6—H6 | 120.2 | O4—C18—H18A | 109.5 |
O3—C7—C6 | 123.55 (15) | O4—C18—H18B | 109.5 |
O3—C7—C8 | 116.18 (16) | H18A—C18—H18B | 109.5 |
C6—C7—C8 | 120.26 (16) | O4—C18—H18C | 109.5 |
C9—C8—C7 | 119.28 (16) | H18A—C18—H18C | 109.5 |
C9—C8—H8 | 120.4 | H18B—C18—H18C | 109.5 |
C7—C8—H8 | 120.4 | O5—C19—H19A | 109.5 |
C8—C9—C4 | 122.75 (16) | O5—C19—H19B | 109.5 |
C8—C9—H9 | 118.6 | H19A—C19—H19B | 109.5 |
C4—C9—H9 | 118.6 | O5—C19—H19C | 109.5 |
C15—C10—C11 | 119.75 (15) | H19A—C19—H19C | 109.5 |
C15—C10—C1 | 122.81 (15) | H19B—C19—H19C | 109.5 |
C11—C10—C1 | 117.44 (15) | O6—C20—H20A | 109.5 |
C12—C11—C10 | 120.55 (16) | O6—C20—H20B | 109.5 |
C12—C11—H11 | 119.7 | H20A—C20—H20B | 109.5 |
C10—C11—H11 | 119.7 | O6—C20—H20C | 109.5 |
O4—C12—C11 | 124.89 (16) | H20A—C20—H20C | 109.5 |
O4—C12—C13 | 115.31 (14) | H20B—C20—H20C | 109.5 |
O1—C1—C2—C3 | −10.4 (3) | O1—C1—C10—C11 | 0.4 (3) |
C10—C1—C2—C3 | 169.13 (18) | C2—C1—C10—C11 | −179.08 (17) |
C1—C2—C3—C4 | −177.75 (18) | C15—C10—C11—C12 | −0.4 (3) |
C2—C3—C4—C9 | −3.8 (3) | C1—C10—C11—C12 | 179.24 (17) |
C2—C3—C4—C5 | 175.28 (19) | C18—O4—C12—C11 | −4.6 (3) |
C17—O2—C5—C6 | 2.4 (2) | C18—O4—C12—C13 | 175.86 (16) |
C17—O2—C5—C4 | −178.70 (15) | C10—C11—C12—O4 | 179.65 (16) |
C9—C4—C5—O2 | −175.91 (14) | C10—C11—C12—C13 | −0.8 (3) |
C3—C4—C5—O2 | 5.0 (2) | C19—O5—C13—C14 | 94.45 (19) |
C9—C4—C5—C6 | 3.0 (2) | C19—O5—C13—C12 | −87.4 (2) |
C3—C4—C5—C6 | −176.14 (16) | O4—C12—C13—O5 | 3.3 (2) |
O2—C5—C6—C7 | 176.89 (15) | C11—C12—C13—O5 | −176.24 (15) |
C4—C5—C6—C7 | −1.9 (3) | O4—C12—C13—C14 | −178.56 (15) |
C16—O3—C7—C6 | 0.5 (3) | C11—C12—C13—C14 | 1.9 (3) |
C16—O3—C7—C8 | −178.72 (18) | C20—O6—C14—C15 | 7.9 (3) |
C5—C6—C7—O3 | −179.56 (16) | C20—O6—C14—C13 | −171.57 (17) |
C5—C6—C7—C8 | −0.4 (3) | O5—C13—C14—O6 | −4.1 (2) |
O3—C7—C8—C9 | −179.29 (16) | C12—C13—C14—O6 | 177.80 (15) |
C6—C7—C8—C9 | 1.5 (3) | O5—C13—C14—C15 | 176.41 (15) |
C7—C8—C9—C4 | −0.3 (3) | C12—C13—C14—C15 | −1.7 (3) |
C5—C4—C9—C8 | −1.9 (3) | O6—C14—C15—C10 | −178.97 (16) |
C3—C4—C9—C8 | 177.22 (17) | C13—C14—C15—C10 | 0.5 (3) |
O1—C1—C10—C15 | −180.0 (2) | C11—C10—C15—C14 | 0.6 (3) |
C2—C1—C10—C15 | 0.6 (3) | C1—C10—C15—C14 | −179.05 (17) |
Cg1 is the centroid of the C4–C9 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O6i | 0.93 | 2.65 | 3.562 (2) | 166 |
C18—H18B···O3ii | 0.96 | 2.64 | 3.404 (2) | 136 |
C16—H16B···O2iii | 0.96 | 2.68 | 3.389 (2) | 132 |
C16—H16C···O1iii | 0.96 | 2.66 | 3.608 (3) | 169 |
C19—H19C···Cg1iv | 0.96 | 2.79 | 3.530 (2) | 134 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y, z−1; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H22O6 |
Mr | 358.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.3111 (11), 13.8493 (17), 15.887 (2) |
β (°) | 101.588 (2) |
V (Å3) | 1791.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.37 × 0.31 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.651, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9663, 3512, 2452 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.126, 0.97 |
No. of reflections | 3512 |
No. of parameters | 241 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg1 is the centroid of the C4–C9 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O6i | 0.93 | 2.65 | 3.562 (2) | 166 |
C18—H18B···O3ii | 0.96 | 2.64 | 3.404 (2) | 136 |
C16—H16B···O2iii | 0.96 | 2.68 | 3.389 (2) | 132 |
C16—H16C···O1iii | 0.96 | 2.66 | 3.608 (3) | 169 |
C19—H19C···Cg1iv | 0.96 | 2.79 | 3.530 (2) | 134 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y, z−1; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z. |
Acknowledgements
The authors are grateful to the associate researcher Sun Jie from Shanghai Institute of Organic Chemistry, Chinese academy of Sciences for testing and crystal analysis. This study was partially supported by the Zhejiang Natural Science Funds (Y2101108) and the University Students in Zhejiang Science and Technology Innovation Projects (2011R413025).
References
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Chalcones are characterized by possessing two aromatic rings linked by a three-carbon α,β-unsaturated carbonyl system (Wu et al., 2010; Wu et al., 2011). Natural chalcones have many kinds of active biological properties such as antiinflammatory, antitumoral, antimalarial, antileishmanial, Antibacterial. Investigations have demonstrated that synthetical chalcones have the same biological properties as natural chalcones. (Wu et al. 2010; Wu et al. 2011; Nielsen et al. 2005). In order to study its anticancer agents, we have synthesized the title chalcone derivative and herein its crystal structure is reported. The crystal structure parameters are similar to those found in some analogous structures reported in the literature (Peng et al., 2010; Huang et al., 2010).The dihedral angle between the mean planes of the phenyl rings is 15.77 (6)°. The H atoms of the central C=C double bond are in a trans configuration. In the crystal structure, there are many weak C–H···O intermolecular contacts (Table 1) but no classic hydrogen bonds between the molecules (Spek, 2009).