Literature DB >> 21754811

(E)-1-(4-Meth-oxy-phen-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.

Yuepiao Cai, Zhankun Wang, Zhe Li, Meiling Zhang, Jianzhang Wu.   

Abstract

In the title compound, C(19)H(20)O(5), the dihedral angle between the two aromatic rings is 18.23 (4)°. The crystal structure exhibits only weak C-H⋯π and C-H⋯O contacts between the mol-ecules.

Entities:  

Year:  2011        PMID： 21754811      PMCID： PMC3120626          DOI： 10.1107/S1600536811017788

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


Related literature

For related structures, see: Wu et al. (2011 ▶); Peng et al. (2010 ▶); Huang et al. (2010 ▶); Zhao et al. (2010 ▶). For background and applications of chalcones, see: Wu et al. (2010 ▶, 2011) ▶; Liu et al. (2008 ▶); Zhao et al. (2010 ▶); Nielsen et al. (2005 ▶).

Experimental

Crystal data

C19H20O5 M = 328.35 Orthorhombic, a = 7.3339 (6) Å b = 16.8260 (14) Å c = 26.677 (2) Å V = 3291.9 (5) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 133 K 0.35 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.967, T max = 0.971 22257 measured reflections 3593 independent reflections 3380 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.108 S = 1.02 3593 reflections 221 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.24 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 datablocks I, global. DOI: 10.1107/S1600536811017788/ff2009sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017788/ff2009Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811017788/ff2009Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H20O5F(000) = 1392
Mr = 328.35Dx = 1.325 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9911 reflections
a = 7.3339 (6) Åθ = 2.5–27.5°
b = 16.8260 (14) ŵ = 0.10 mm−1
c = 26.677 (2) ÅT = 133 K
V = 3291.9 (5) Å3Block, colourless
Z = 80.35 × 0.33 × 0.31 mm
Bruker SMART APEX CCD diffractometer3593 independent reflections
Radiation source: fine-focus sealed tube3380 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −9→8
Tmin = 0.967, Tmax = 0.971k = −21→21
22257 measured reflectionsl = −34→33
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0656P)2 + 1.0603P] where P = (Fo2 + 2Fc2)/3
3593 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
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
O1−0.11440 (12)0.09104 (5)0.52298 (3)0.0306 (2)
O20.09328 (11)0.52918 (4)0.42318 (3)0.02358 (18)
O30.15756 (13)0.77278 (5)0.33786 (3)0.0297 (2)
O4−0.01580 (13)0.53324 (5)0.24951 (3)0.0297 (2)
O5−0.12136 (16)0.28670 (6)0.32160 (3)0.0432 (3)
C1−0.17359 (15)0.18362 (6)0.40208 (4)0.0236 (2)
H1−0.23340.17160.37140.028*
C2−0.18310 (15)0.13044 (6)0.44147 (4)0.0249 (2)
H2−0.24960.08230.43780.030*
C3−0.09526 (15)0.14727 (6)0.48666 (4)0.0231 (2)
C40.00426 (15)0.21720 (6)0.49199 (4)0.0237 (2)
H40.06600.22850.52250.028*
C50.01209 (15)0.27031 (6)0.45199 (4)0.0228 (2)
H50.07970.31810.45560.027*
C6−0.07673 (14)0.25507 (6)0.40679 (4)0.0217 (2)
C7−0.07394 (16)0.31067 (7)0.36306 (4)0.0255 (2)
C8−0.01821 (16)0.39334 (7)0.37223 (4)0.0250 (2)
H80.01550.40910.40510.030*
C9−0.01402 (15)0.44698 (7)0.33494 (4)0.0238 (2)
H9−0.04860.42730.30290.029*
C100.03548 (14)0.53061 (6)0.33628 (4)0.0212 (2)
C110.08965 (14)0.57253 (6)0.37997 (4)0.0206 (2)
C120.13343 (15)0.65221 (6)0.37886 (4)0.0227 (2)
H120.17260.67840.40850.027*
C130.11981 (15)0.69401 (6)0.33384 (4)0.0231 (2)
C140.07144 (15)0.65615 (7)0.28945 (4)0.0239 (2)
H140.06530.68470.25880.029*
C150.03215 (15)0.57507 (7)0.29121 (4)0.0226 (2)
C16−0.0194 (2)0.10198 (8)0.56923 (5)0.0365 (3)
H16A0.11160.10670.56260.055*
H16B−0.04160.05630.59120.055*
H16C−0.06310.15050.58560.055*
C170.15775 (17)0.56770 (7)0.46741 (4)0.0274 (2)
H17A0.28260.58660.46190.041*
H17B0.15630.53000.49540.041*
H17C0.07870.61300.47520.041*
C180.1300 (2)0.82163 (7)0.29468 (5)0.0364 (3)
H18A0.20940.80340.26750.055*
H18B0.15950.87690.30290.055*
H18C0.00240.81810.28400.055*
C190.02210 (17)0.56754 (7)0.20163 (4)0.0286 (3)
H19A−0.05310.61510.19700.043*
H19B−0.00590.52890.17520.043*
H19C0.15130.58210.19980.043*
U11U22U33U12U13U23
O10.0364 (5)0.0276 (4)0.0278 (4)−0.0038 (3)−0.0007 (3)0.0050 (3)
O20.0312 (4)0.0216 (4)0.0179 (4)−0.0018 (3)−0.0029 (3)−0.0002 (3)
O30.0428 (5)0.0211 (4)0.0253 (4)−0.0041 (3)−0.0032 (3)0.0026 (3)
O40.0398 (5)0.0312 (4)0.0182 (4)−0.0090 (4)−0.0033 (3)0.0003 (3)
O50.0722 (7)0.0338 (5)0.0238 (4)−0.0168 (5)−0.0113 (4)−0.0003 (3)
C10.0224 (5)0.0244 (5)0.0240 (5)−0.0017 (4)−0.0004 (4)−0.0042 (4)
C20.0225 (5)0.0223 (5)0.0299 (6)−0.0043 (4)0.0014 (4)−0.0021 (4)
C30.0218 (5)0.0223 (5)0.0251 (5)0.0029 (4)0.0040 (4)0.0012 (4)
C40.0238 (5)0.0245 (5)0.0229 (5)0.0009 (4)−0.0014 (4)−0.0034 (4)
C50.0238 (5)0.0203 (5)0.0241 (5)−0.0022 (4)0.0005 (4)−0.0034 (4)
C60.0220 (5)0.0210 (5)0.0222 (5)−0.0001 (4)0.0021 (4)−0.0032 (4)
C70.0296 (6)0.0251 (5)0.0219 (5)−0.0029 (4)−0.0009 (4)−0.0017 (4)
C80.0289 (5)0.0245 (5)0.0218 (5)−0.0022 (4)−0.0001 (4)−0.0026 (4)
C90.0240 (5)0.0245 (5)0.0228 (5)−0.0017 (4)−0.0008 (4)−0.0029 (4)
C100.0192 (5)0.0228 (5)0.0216 (5)0.0000 (4)0.0004 (4)0.0001 (4)
C110.0179 (5)0.0243 (5)0.0195 (5)0.0020 (4)0.0011 (4)0.0011 (4)
C120.0238 (5)0.0236 (5)0.0207 (5)0.0001 (4)0.0003 (4)−0.0015 (4)
C130.0218 (5)0.0216 (5)0.0258 (5)−0.0006 (4)0.0018 (4)0.0007 (4)
C140.0239 (5)0.0270 (5)0.0206 (5)−0.0003 (4)−0.0003 (4)0.0026 (4)
C150.0202 (5)0.0275 (5)0.0202 (5)−0.0007 (4)−0.0007 (4)−0.0013 (4)
C160.0475 (8)0.0368 (7)0.0252 (6)−0.0010 (6)−0.0025 (5)0.0057 (5)
C170.0367 (6)0.0252 (5)0.0204 (5)−0.0020 (5)−0.0060 (4)−0.0009 (4)
C180.0507 (8)0.0267 (6)0.0319 (6)−0.0080 (5)−0.0088 (6)0.0085 (5)
C190.0315 (6)0.0354 (6)0.0189 (5)−0.0007 (5)−0.0016 (4)0.0014 (4)
O1—C31.3615 (13)C9—C101.4538 (15)
O1—C161.4287 (15)C9—H90.9500
O2—C111.3643 (12)C10—C151.4163 (14)
O2—C171.4269 (12)C10—C111.4191 (14)
O3—C131.3584 (13)C11—C121.3789 (15)
O3—C181.4294 (13)C12—C131.3954 (15)
O4—C151.3623 (13)C12—H120.9500
O4—C191.4290 (13)C13—C141.3907 (15)
O5—C71.2275 (14)C14—C151.3951 (16)
C1—C21.3818 (15)C14—H140.9500
C1—C61.4021 (15)C16—H16A0.9800
C1—H10.9500C16—H16B0.9800
C2—C31.3959 (16)C16—H16C0.9800
C2—H20.9500C17—H17A0.9800
C3—C41.3919 (15)C17—H17B0.9800
C4—C51.3931 (15)C17—H17C0.9800
C4—H40.9500C18—H18A0.9800
C5—C61.3941 (15)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.4955 (15)C19—H19A0.9800
C7—C81.4703 (15)C19—H19B0.9800
C8—C91.3435 (15)C19—H19C0.9800
C8—H80.9500
C3—O1—C16118.34 (9)C11—C12—C13119.46 (10)
C11—O2—C17117.53 (8)C11—C12—H12120.3
C13—O3—C18117.94 (9)C13—C12—H12120.3
C15—O4—C19118.10 (9)O3—C13—C14124.49 (10)
C2—C1—C6120.84 (10)O3—C13—C12114.15 (9)
C2—C1—H1119.6C14—C13—C12121.36 (10)
C6—C1—H1119.6C13—C14—C15118.16 (10)
C1—C2—C3120.13 (10)C13—C14—H14120.9
C1—C2—H2119.9C15—C14—H14120.9
C3—C2—H2119.9O4—C15—C14122.07 (10)
O1—C3—C4124.67 (10)O4—C15—C10115.14 (9)
O1—C3—C2115.22 (10)C14—C15—C10122.78 (10)
C4—C3—C2120.11 (10)O1—C16—H16A109.5
C3—C4—C5119.05 (10)O1—C16—H16B109.5
C3—C4—H4120.5H16A—C16—H16B109.5
C5—C4—H4120.5O1—C16—H16C109.5
C4—C5—C6121.69 (10)H16A—C16—H16C109.5
C4—C5—H5119.2H16B—C16—H16C109.5
C6—C5—H5119.2O2—C17—H17A109.5
C5—C6—C1118.16 (10)O2—C17—H17B109.5
C5—C6—C7123.58 (10)H17A—C17—H17B109.5
C1—C6—C7118.26 (9)O2—C17—H17C109.5
O5—C7—C8122.65 (10)H17A—C17—H17C109.5
O5—C7—C6119.56 (10)H17B—C17—H17C109.5
C8—C7—C6117.76 (9)O3—C18—H18A109.5
C9—C8—C7121.24 (10)O3—C18—H18B109.5
C9—C8—H8119.4H18A—C18—H18B109.5
C7—C8—H8119.4O3—C18—H18C109.5
C8—C9—C10129.63 (10)H18A—C18—H18C109.5
C8—C9—H9115.2H18B—C18—H18C109.5
C10—C9—H9115.2O4—C19—H19A109.5
C15—C10—C11116.08 (9)O4—C19—H19B109.5
C15—C10—C9119.08 (9)H19A—C19—H19B109.5
C11—C10—C9124.83 (9)O4—C19—H19C109.5
O2—C11—C12122.24 (9)H19A—C19—H19C109.5
O2—C11—C10115.70 (9)H19B—C19—H19C109.5
C12—C11—C10122.06 (10)
C6—C1—C2—C3−0.21 (16)C10—C11—O2—C17176.22 (9)
C16—O1—C3—C4−3.10 (16)C15—C10—C11—O2−179.71 (9)
C2—C3—O1—C16176.37 (10)C9—C10—C11—O2−0.21 (15)
C1—C2—C3—O1179.65 (10)C15—C10—C11—C121.10 (15)
C1—C2—C3—C4−0.85 (16)C9—C10—C11—C12−179.40 (10)
O1—C3—C4—C5−179.52 (10)O2—C11—C12—C13−177.37 (10)
C2—C3—C4—C51.03 (16)C10—C11—C12—C131.76 (16)
C3—C4—C5—C6−0.17 (16)C18—O3—C13—C145.92 (17)
C4—C5—C6—C1−0.86 (16)C12—C13—O3—C18−174.09 (10)
C4—C5—C6—C7179.29 (10)C11—C12—C13—O3176.86 (10)
C2—C1—C6—C51.04 (16)C11—C12—C13—C14−3.16 (16)
C2—C1—C6—C7−179.09 (10)O3—C13—C14—C15−178.47 (10)
C5—C6—C7—O5164.74 (12)C12—C13—C14—C151.56 (17)
C1—C6—C7—O5−15.12 (16)C14—C15—O4—C1916.90 (16)
C5—C6—C7—C8−16.87 (16)C19—O4—C15—C10−164.29 (10)
C1—C6—C7—C8163.27 (10)C13—C14—C15—O4−179.79 (10)
O5—C7—C8—C9−1.00 (19)C13—C14—C15—C101.49 (17)
C6—C7—C8—C9−179.34 (10)C11—C10—C15—O4178.43 (9)
C7—C8—C9—C10179.64 (11)C9—C10—C15—O4−1.10 (15)
C8—C9—C10—C15178.89 (11)C11—C10—C15—C14−2.77 (16)
C8—C9—C10—C11−0.59 (19)C9—C10—C15—C14177.70 (10)
C17—O2—C11—C12−4.60 (15)
Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1···Cg2i0.952.893.6744 (12)140
C4—H4···Cg1ii0.952.943.6921 (12)137
C17—H17a···Cg1iii0.982.963.8913 (13)159
C19—H19a···Cg2iv0.982.823.4705 (13)125
C16—H16c···O3v0.982.513.4074 (16)152
C18—H18a···O5vi0.982.483.1578 (16)126
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1—H1⋯Cg2i0.952.893.6744 (12)140
C4—H4⋯Cg1ii0.952.943.6921 (12)137
C17—H17a⋯Cg1iii0.982.963.8913 (13)159
C19—H19a⋯Cg2iv0.982.823.4705 (13)125
C16—H16c⋯O3v0.982.513.4074 (16)152
C18—H18a⋯O5vi0.982.483.1578 (16)126

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

  6 in total

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Journal:  Bioorg Med Chem       Date:  2010-03-06       Impact factor: 3.641

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

Authors:  Simon F Nielsen; Mogens Larsen; Thomas Boesen; Kristian Schønning; Hasse Kromann
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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.  Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus.

Authors:  X L Liu; Y J Xu; M L Go
Journal:  Eur J Med Chem       Date:  2007-10-11       Impact factor: 6.514

6.  (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 in total
  1 in total

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

Authors:  P S Carvalho; L O Sallum; A F Cidade; G L B Aquino; H B Napolitano
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-23
  1 in total

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