Literature DB >> 22259440

(E)-3-(2,4-Dimeth-oxy-phen-yl)-1-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Jianzhang Wu, Junyan Qiu, Xiaokai Wu, Shulin Yang, Yonggen Liu.   

Abstract

In the title chalcone derivative, C(20)H(22)O(6), 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.

Entities:  

Year:  2011        PMID： 22259440      PMCID： PMC3254497          DOI： 10.1107/S1600536811053001

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Wu et al. (2010 ▶, 2011 ▶); Huang et al. (2010 ▶); Peng et al. (2010 ▶). For applications of chalcones, see: Wu et al. (2010 ▶, 2011 ▶); Nielsen et al. (2005 ▶). For the hydrogen-bond analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C20H22O6 M = 358.38 Monoclinic, a = 8.3111 (11) Å b = 13.8493 (17) Å c = 15.887 (2) Å β = 101.588 (2)° V = 1791.4 (4) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 293 K 0.40 × 0.37 × 0.31 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.651, T max = 1.000 9663 measured reflections 3512 independent reflections 2452 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.126 S = 0.97 3512 reflections 241 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: 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. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053001/zq2146sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053001/zq2146Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811053001/zq2146Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H22O6F(000) = 760
Mr = 358.38Dx = 1.329 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2728 reflections
a = 8.3111 (11) Åθ = 5.2–49.2°
b = 13.8493 (17) ŵ = 0.10 mm−1
c = 15.887 (2) ÅT = 293 K
β = 101.588 (2)°Prismatic, green
V = 1791.4 (4) Å30.40 × 0.37 × 0.31 mm
Z = 4
Bruker SMART CCD diffractometer3512 independent reflections
Radiation source: fine-focus sealed tube2452 reflections with I > 2σ(I)
graphiteRint = 0.045
phi and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −10→9
Tmin = 0.651, Tmax = 1.000k = −17→15
9663 measured reflectionsl = −16→19
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.126w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3512 reflectionsΔρmax = 0.20 e Å−3
241 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0069 (15)
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.
xyzUiso*/Ueq
O10.3078 (3)0.60842 (10)−0.03257 (9)0.0969 (7)
O20.45908 (16)0.73756 (8)0.24726 (7)0.0510 (4)
O30.34229 (18)0.58134 (9)0.49898 (7)0.0629 (4)
O40.20538 (17)0.38935 (8)−0.28996 (7)0.0549 (4)
O50.11723 (15)0.21987 (8)−0.23292 (7)0.0487 (3)
O60.07241 (18)0.19802 (8)−0.07336 (8)0.0614 (4)
C10.2622 (3)0.53394 (12)−0.00427 (11)0.0532 (5)
C20.2513 (2)0.52558 (12)0.08616 (11)0.0494 (5)
H20.19940.47190.10370.059*
C30.3124 (2)0.59147 (12)0.14391 (11)0.0478 (5)
H30.35970.64500.12310.057*
C40.3155 (2)0.59116 (11)0.23532 (10)0.0397 (4)
C50.3969 (2)0.66447 (11)0.28813 (10)0.0395 (4)
C60.4097 (2)0.66259 (11)0.37629 (10)0.0438 (4)
H60.46700.71090.41040.053*
C70.3368 (2)0.58853 (12)0.41331 (11)0.0454 (4)
C80.2505 (2)0.51675 (12)0.36245 (12)0.0495 (5)
H80.19930.46770.38720.059*
C90.2416 (2)0.51894 (11)0.27580 (11)0.0456 (5)
H90.18390.47030.24230.055*
C100.2178 (2)0.44929 (11)−0.06312 (10)0.0441 (5)
C110.2324 (2)0.46042 (11)−0.14787 (11)0.0451 (4)
H110.26750.5192−0.16620.054*
C120.1956 (2)0.38529 (11)−0.20524 (10)0.0428 (4)
C130.1453 (2)0.29723 (11)−0.17775 (10)0.0407 (4)
C140.1279 (2)0.28626 (11)−0.09326 (11)0.0436 (4)
C150.1647 (2)0.36210 (11)−0.03595 (11)0.0468 (5)
H150.15380.35450.02080.056*
C160.4271 (3)0.65505 (15)0.55295 (12)0.0817 (8)
H16A0.54150.65340.55050.123*
H16B0.41470.64450.61100.123*
H16C0.38210.71690.53360.123*
C170.5458 (2)0.81254 (12)0.29860 (11)0.0517 (5)
H17A0.47510.84210.33210.078*
H17B0.58050.86010.26210.078*
H17C0.64020.78590.33630.078*
C180.2455 (3)0.47971 (13)−0.32250 (12)0.0632 (6)
H18A0.16290.5263−0.31680.095*
H18B0.25080.4730−0.38200.095*
H18C0.35010.5010−0.29070.095*
C19−0.0442 (2)0.21605 (14)−0.28238 (13)0.0635 (6)
H19A−0.12040.2052−0.24520.095*
H19B−0.05230.1643−0.32320.095*
H19C−0.06970.2761−0.31230.095*
C200.0313 (3)0.18677 (15)0.00746 (13)0.0796 (7)
H20A0.12800.19430.05150.119*
H20B−0.01410.12360.01150.119*
H20C−0.04830.23470.01470.119*
U11U22U33U12U13U23
O10.196 (2)0.0472 (8)0.0459 (9)−0.0398 (10)0.0199 (10)−0.0057 (6)
O20.0720 (9)0.0430 (7)0.0373 (7)−0.0161 (6)0.0091 (6)−0.0008 (5)
O30.1002 (12)0.0532 (8)0.0383 (7)−0.0019 (7)0.0214 (7)0.0041 (6)
O40.0851 (10)0.0457 (7)0.0366 (7)−0.0065 (6)0.0188 (6)−0.0026 (5)
O50.0564 (8)0.0391 (6)0.0498 (7)0.0031 (6)0.0088 (6)−0.0121 (5)
O60.0974 (11)0.0389 (7)0.0520 (8)−0.0099 (7)0.0252 (7)−0.0010 (6)
C10.0786 (14)0.0389 (10)0.0384 (10)−0.0011 (9)0.0028 (9)−0.0016 (8)
C20.0649 (13)0.0396 (9)0.0429 (10)−0.0037 (9)0.0092 (9)−0.0034 (8)
C30.0658 (13)0.0363 (9)0.0400 (10)−0.0048 (8)0.0076 (8)−0.0006 (7)
C40.0486 (11)0.0334 (8)0.0364 (9)0.0030 (7)0.0067 (8)−0.0017 (7)
C50.0473 (10)0.0338 (8)0.0375 (9)−0.0002 (7)0.0087 (8)0.0010 (7)
C60.0574 (12)0.0376 (9)0.0353 (9)−0.0013 (8)0.0065 (8)−0.0034 (7)
C70.0625 (12)0.0395 (9)0.0361 (10)0.0095 (8)0.0141 (8)0.0039 (7)
C80.0659 (13)0.0354 (9)0.0514 (11)−0.0025 (8)0.0217 (9)0.0041 (8)
C90.0551 (12)0.0338 (9)0.0484 (11)−0.0019 (8)0.0119 (9)−0.0064 (7)
C100.0560 (12)0.0377 (9)0.0353 (9)0.0018 (8)0.0018 (8)−0.0013 (7)
C110.0581 (12)0.0353 (9)0.0410 (10)−0.0034 (8)0.0078 (8)0.0011 (7)
C120.0520 (11)0.0412 (9)0.0354 (9)0.0038 (8)0.0094 (8)−0.0016 (7)
C130.0466 (11)0.0343 (9)0.0402 (10)0.0047 (7)0.0066 (8)−0.0052 (7)
C140.0537 (11)0.0328 (9)0.0440 (10)0.0007 (8)0.0086 (8)0.0008 (7)
C150.0641 (13)0.0422 (10)0.0334 (9)0.0020 (9)0.0082 (8)0.0010 (7)
C160.138 (2)0.0694 (14)0.0348 (11)−0.0064 (14)0.0103 (12)−0.0023 (10)
C170.0619 (13)0.0421 (10)0.0515 (11)−0.0131 (9)0.0125 (9)−0.0037 (8)
C180.0934 (17)0.0537 (12)0.0456 (11)−0.0055 (11)0.0211 (11)0.0058 (9)
C190.0649 (14)0.0589 (12)0.0627 (13)−0.0058 (10)0.0032 (10)−0.0159 (10)
C200.117 (2)0.0644 (14)0.0642 (14)−0.0289 (14)0.0338 (13)0.0030 (11)
O1—C11.216 (2)C9—H90.9300
O2—C51.3595 (19)C10—C151.384 (2)
O2—C171.4235 (18)C10—C111.385 (2)
O3—C71.3564 (19)C11—C121.377 (2)
O3—C161.425 (2)C11—H110.9300
O4—C121.366 (2)C12—C131.388 (2)
O4—C181.419 (2)C13—C141.387 (2)
O5—C131.3742 (18)C14—C151.383 (2)
O5—C191.413 (2)C15—H150.9300
O6—C141.3656 (19)C16—H16A0.9600
O6—C201.402 (2)C16—H16B0.9600
C1—C21.462 (2)C16—H16C0.9600
C1—C101.499 (2)C17—H17A0.9600
C2—C31.321 (2)C17—H17B0.9600
C2—H20.9300C17—H17C0.9600
C3—C41.447 (2)C18—H18A0.9600
C3—H30.9300C18—H18B0.9600
C4—C91.396 (2)C18—H18C0.9600
C4—C51.402 (2)C19—H19A0.9600
C5—C61.383 (2)C19—H19B0.9600
C6—C71.381 (2)C19—H19C0.9600
C6—H60.9300C20—H20A0.9600
C7—C81.387 (2)C20—H20B0.9600
C8—C91.364 (2)C20—H20C0.9600
C8—H80.9300
C5—O2—C17117.82 (13)C11—C12—C13119.79 (16)
C7—O3—C16117.64 (15)O5—C13—C14119.64 (14)
C12—O4—C18117.40 (13)O5—C13—C12120.52 (15)
C13—O5—C19113.86 (13)C14—C13—C12119.82 (14)
C14—O6—C20117.86 (14)O6—C14—C15124.57 (16)
O1—C1—C2121.06 (15)O6—C14—C13115.33 (14)
O1—C1—C10119.26 (16)C15—C14—C13120.10 (15)
C2—C1—C10119.67 (15)C14—C15—C10119.96 (16)
C3—C2—C1122.45 (17)C14—C15—H15120.0
C3—C2—H2118.8C10—C15—H15120.0
C1—C2—H2118.8O3—C16—H16A109.5
C2—C3—C4128.42 (17)O3—C16—H16B109.5
C2—C3—H3115.8H16A—C16—H16B109.5
C4—C3—H3115.8O3—C16—H16C109.5
C9—C4—C5116.56 (15)H16A—C16—H16C109.5
C9—C4—C3122.93 (14)H16B—C16—H16C109.5
C5—C4—C3120.50 (15)O2—C17—H17A109.5
O2—C5—C6122.56 (14)O2—C17—H17B109.5
O2—C5—C4115.95 (14)H17A—C17—H17B109.5
C6—C5—C4121.48 (15)O2—C17—H17C109.5
C7—C6—C5119.61 (15)H17A—C17—H17C109.5
C7—C6—H6120.2H17B—C17—H17C109.5
C5—C6—H6120.2O4—C18—H18A109.5
O3—C7—C6123.55 (15)O4—C18—H18B109.5
O3—C7—C8116.18 (16)H18A—C18—H18B109.5
C6—C7—C8120.26 (16)O4—C18—H18C109.5
C9—C8—C7119.28 (16)H18A—C18—H18C109.5
C9—C8—H8120.4H18B—C18—H18C109.5
C7—C8—H8120.4O5—C19—H19A109.5
C8—C9—C4122.75 (16)O5—C19—H19B109.5
C8—C9—H9118.6H19A—C19—H19B109.5
C4—C9—H9118.6O5—C19—H19C109.5
C15—C10—C11119.75 (15)H19A—C19—H19C109.5
C15—C10—C1122.81 (15)H19B—C19—H19C109.5
C11—C10—C1117.44 (15)O6—C20—H20A109.5
C12—C11—C10120.55 (16)O6—C20—H20B109.5
C12—C11—H11119.7H20A—C20—H20B109.5
C10—C11—H11119.7O6—C20—H20C109.5
O4—C12—C11124.89 (16)H20A—C20—H20C109.5
O4—C12—C13115.31 (14)H20B—C20—H20C109.5
O1—C1—C2—C3−10.4 (3)O1—C1—C10—C110.4 (3)
C10—C1—C2—C3169.13 (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—C12179.24 (17)
C2—C3—C4—C5175.28 (19)C18—O4—C12—C11−4.6 (3)
C17—O2—C5—C62.4 (2)C18—O4—C12—C13175.86 (16)
C17—O2—C5—C4−178.70 (15)C10—C11—C12—O4179.65 (16)
C9—C4—C5—O2−175.91 (14)C10—C11—C12—C13−0.8 (3)
C3—C4—C5—O25.0 (2)C19—O5—C13—C1494.45 (19)
C9—C4—C5—C63.0 (2)C19—O5—C13—C12−87.4 (2)
C3—C4—C5—C6−176.14 (16)O4—C12—C13—O53.3 (2)
O2—C5—C6—C7176.89 (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—C60.5 (3)C11—C12—C13—C141.9 (3)
C16—O3—C7—C8−178.72 (18)C20—O6—C14—C157.9 (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—O6177.80 (15)
C6—C7—C8—C91.5 (3)O5—C13—C14—C15176.41 (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—C8177.22 (17)C13—C14—C15—C100.5 (3)
O1—C1—C10—C15−180.0 (2)C11—C10—C15—C140.6 (3)
C2—C1—C10—C150.6 (3)C1—C10—C15—C14−179.05 (17)
Cg1 is the centroid of the C4–C9 ring.
D—H···A
—···
—···
—···
—···
—···
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8⋯O6i0.932.653.562 (2)166
C18—H18B⋯O3ii0.962.643.404 (2)136
C16—H16B⋯O2iii0.962.683.389 (2)132
C16—H16C⋯O1iii0.962.663.608 (3)169
C19—H19C⋯Cg1iv0.962.793.530 (2)134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  6 in total

1.  Evaluation and discovery of novel synthetic chalcone derivatives as anti-inflammatory agents.

Authors:  Jianzhang Wu; Jianling Li; Yuepiao Cai; Yong Pan; Faqing Ye; Yali Zhang; Yunjie Zhao; Shulin Yang; Xiaokun Li; Guang Liang
Journal:  J Med Chem       Date:  2011-11-04       Impact factor: 7.446

2.  Cationic chalcone antibiotics. Design, synthesis, and mechanism of action.

Authors:  Simon F Nielsen; Mogens Larsen; Thomas Boesen; Kristian Schønning; Hasse Kromann
Journal:  J Med Chem       Date:  2005-04-07       Impact factor: 7.446

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  1-(4-Amino-phen-yl)-3-[2-(trifluoro-meth-yl)phen-yl]prop-2-en-1-one.

Authors:  Jing Peng; Huifen Xu; Zhe Li; Yuyan Zhang; Jianzhang Wu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-24

5.  (E)-1-(3,5-Difluoro-phen-yl)-3-(2,4-dimeth-oxy-phen-yl)prop-2-en-1-one.

Authors:  Tanxiao Huang; Dongdong Zhang; Quanzhi Yang; Xiaoyan Wei; Jianzhang Wu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  (E)-1-(3,5-Di-meth-oxy-phen-yl)-3-(3-meth-oxy-phen-yl)prop-2-en-1-one.

Authors:  Seunghyun Ahn; Ha-Jin Lee; Yoongho Lim; Dongsoo Koh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-05
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.