Literature DB >> 21754113

1-(2-Hy-droxy-4-meth-oxy-phen-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one.

G B Thippeswamy, D Vijay Kumar, B S Jayashree, M A Sridhar, J Shashidhara Prasad.   

Abstract

The mol-ecule of the title compound, C(17)H(16)O(3), exists in the E conformation with respect to the central C=C bond, is almost planar(r.m.s. deviation = 0.003 Å) and has an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions.

Entities:  

Year:  2011        PMID： 21754113      PMCID： PMC3100019          DOI： 10.1107/S1600536811007586

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


Related literature

For the biological activity of compounds with a chalcone backbone, see: Jayashree et al. (2009 ▶); Epifano et al. (2007 ▶); Onyilagna et al. (1997 ▶); Satyanarayana et al. (2004 ▶); Deshpande et al. (1999 ▶); Hsieh et al. (2000 ▶); Khatib et al. (2005 ▶); Barford et al. (2002 ▶); Nielsen et al. (1995 ▶); Severi et al. (1998 ▶); Siva Kumar et al. (2007 ▶). For a related structure, see: Thippeswamy et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H16O3 M = 268.30 Monoclinic, a = 11.340 (2) Å b = 6.8350 (7) Å c = 20.449 (4) Å β = 117.710 (4)° V = 1403.2 (4) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.26 × 0.24 × 0.22 mm

Data collection

MacScience DIPLabo 32001 diffractometer 4137 measured reflections 2346 independent reflections 1502 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.184 S = 1.05 2346 reflections 184 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.15 e Å−3 Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007586/jh2240sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007586/jh2240Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H16O3F(000) = 568
Mr = 268.30Dx = 1.270 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4137 reflections
a = 11.340 (2) Åθ = 2.2–25.0°
b = 6.8350 (7) ŵ = 0.09 mm−1
c = 20.449 (4) ÅT = 293 K
β = 117.710 (4)°Block, yellow
V = 1403.2 (4) Å30.26 × 0.24 × 0.22 mm
Z = 4
MacScience DIPLabo 32001 diffractometer1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 25.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm-1h = −13→13
ω scansk = −7→7
4137 measured reflectionsl = −24→24
2346 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.184w = 1/[σ2(Fo2) + (0.1052P)2 + 0.0529P]
S = 1.05(Δ/σ)max = 0.010
2346 reflectionsΔρmax = 0.15 e Å−3
184 parametersΔρmin = −0.15 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: 0.032 (8)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O110.22698 (19)0.0248 (2)0.50576 (11)0.1003 (8)
O180.4503 (2)0.1776 (2)0.58182 (12)0.1010 (8)
O190.82822 (19)−0.2381 (3)0.68536 (10)0.0952 (8)
C10.2778 (3)−0.1418 (3)0.51232 (13)0.0769 (9)
C20.1894 (3)−0.3084 (4)0.47598 (14)0.0781 (9)
C30.0588 (3)−0.2910 (4)0.44711 (13)0.0788 (9)
C4−0.0439 (2)−0.4376 (4)0.40885 (12)0.0745 (9)
C5−0.0165 (3)−0.6329 (4)0.40093 (13)0.0771 (9)
C6−0.1187 (3)−0.7615 (4)0.36199 (14)0.0829 (10)
C7−0.2504 (3)−0.7042 (4)0.33000 (13)0.0853 (10)
C8−0.2767 (3)−0.5123 (5)0.34017 (15)0.0941 (11)
C9−0.1758 (3)−0.3830 (4)0.37904 (14)0.0876 (10)
C10−0.3608 (3)−0.8452 (5)0.28614 (16)0.1111 (14)
C120.4201 (2)−0.1668 (3)0.55578 (12)0.0695 (8)
C130.4837 (3)−0.3491 (3)0.56897 (14)0.0777 (9)
C140.6169 (3)−0.3701 (3)0.61167 (14)0.0833 (10)
C150.6964 (3)−0.2045 (4)0.64370 (14)0.0771 (9)
C160.6383 (3)−0.0211 (3)0.63231 (14)0.0775 (10)
C170.5025 (3)−0.0035 (3)0.58930 (13)0.0735 (9)
C200.9130 (3)−0.0751 (4)0.71775 (17)0.1034 (12)
H20.22610−0.428000.473300.0940*
H30.02810−0.168300.451800.0950*
H50.07130−0.676200.422100.0920*
H6−0.09840−0.890800.357100.0990*
H8−0.36460−0.470100.320200.1130*
H9−0.19680−0.255300.385500.1050*
H10A−0.42770−0.838000.302300.1670*
H10B−0.32560−0.975700.293400.1670*
H10C−0.39960−0.812200.234700.1670*
H130.43250−0.459800.547700.0930*
H140.65550−0.493600.619700.1000*
H160.690400.089000.653400.0930*
H180.369500.172600.555500.1510*
H20A0.906000.013400.679600.1550*
H20B1.00340−0.119300.745000.1550*
H20C0.88710−0.009100.750500.1550*
U11U22U33U12U13U23
O110.0982 (14)0.0672 (11)0.1254 (16)0.0151 (9)0.0435 (12)0.0038 (10)
O180.1048 (15)0.0578 (10)0.1353 (16)0.0064 (9)0.0516 (12)0.0001 (9)
O190.0834 (14)0.0929 (13)0.1058 (14)0.0051 (10)0.0411 (11)−0.0085 (10)
C10.0879 (18)0.0692 (14)0.0771 (15)0.0051 (12)0.0414 (14)0.0029 (11)
C20.0831 (18)0.0705 (14)0.0819 (16)0.0012 (12)0.0393 (13)−0.0014 (11)
C30.0831 (19)0.0788 (15)0.0731 (15)0.0096 (13)0.0352 (14)0.0036 (12)
C40.0741 (17)0.0851 (16)0.0634 (14)0.0081 (12)0.0313 (12)0.0052 (11)
C50.0742 (16)0.0832 (16)0.0737 (15)0.0129 (12)0.0343 (13)0.0039 (12)
C60.0848 (19)0.0857 (16)0.0788 (16)−0.0035 (14)0.0385 (14)−0.0054 (13)
C70.0818 (19)0.1053 (19)0.0654 (15)−0.0058 (15)0.0314 (13)0.0042 (13)
C80.0705 (17)0.114 (2)0.0881 (18)0.0105 (15)0.0288 (14)0.0126 (16)
C90.0760 (18)0.0920 (17)0.0909 (18)0.0163 (14)0.0355 (15)0.0095 (14)
C100.096 (2)0.141 (3)0.0857 (19)−0.0278 (19)0.0334 (16)−0.0083 (18)
C120.0817 (17)0.0599 (12)0.0743 (14)0.0020 (11)0.0426 (13)0.0004 (10)
C130.0884 (18)0.0621 (13)0.0843 (16)0.0032 (11)0.0415 (14)−0.0045 (11)
C140.096 (2)0.0649 (14)0.0892 (17)0.0089 (12)0.0433 (15)−0.0031 (12)
C150.0809 (18)0.0813 (15)0.0758 (15)0.0040 (13)0.0420 (14)−0.0022 (12)
C160.0836 (19)0.0677 (14)0.0885 (17)−0.0030 (12)0.0461 (15)−0.0061 (12)
C170.0923 (19)0.0577 (13)0.0832 (15)0.0049 (11)0.0514 (14)0.0018 (11)
C200.087 (2)0.112 (2)0.107 (2)−0.0097 (17)0.0417 (17)−0.0209 (17)
O11—C11.255 (3)C14—C151.405 (4)
O18—C171.350 (3)C15—C161.385 (4)
O19—C151.352 (4)C16—C171.378 (5)
O19—C201.419 (4)C2—H20.9300
O18—H180.8200C3—H30.9300
C1—C21.470 (4)C5—H50.9300
C1—C121.445 (4)C6—H60.9300
C2—C31.320 (5)C8—H80.9300
C3—C41.458 (4)C9—H90.9300
C4—C91.379 (4)C10—H10A0.9600
C4—C51.397 (4)C10—H10B0.9600
C5—C61.375 (4)C10—H10C0.9600
C6—C71.380 (5)C13—H130.9300
C7—C81.382 (4)C14—H140.9300
C7—C101.502 (4)C16—H160.9300
C8—C91.370 (5)C20—H20A0.9600
C12—C171.412 (3)C20—H20B0.9600
C12—C131.402 (3)C20—H20C0.9600
C13—C141.356 (5)
O11···O182.502 (3)H2···C52.8200
O18···O112.502 (3)H2···C132.7100
O18···C13i3.282 (3)H2···H52.3100
O11···H32.3900H2···H132.1300
O11···H9ii2.8700H3···O112.3900
O11···H5i2.7200H3···H92.3400
O11···H181.7700H5···O11v2.7200
O18···H13i2.5600H5···C22.8200
C1···C7iii3.540 (4)H5···H22.3100
C3···C5iii3.398 (4)H6···H10B2.3600
C3···C4iii3.551 (4)H8···H10A2.5900
C4···C4iii3.488 (3)H8···C10viii2.9800
C4···C3iii3.551 (4)H9···H32.3400
C5···C3iii3.398 (4)H9···O11ii2.8700
C6···C20iv3.590 (5)H10A···H82.5900
C7···C1iii3.540 (4)H10A···C12iii2.8600
C10···C12iii3.596 (4)H10A···C17iii2.9200
C12···C10iii3.596 (4)H10B···H62.3600
C13···O18v3.282 (3)H13···O18v2.5600
C20···C6iv3.590 (5)H13···C22.6600
C1···H182.3700H13···H22.1300
C2···H132.6600H16···C202.5000
C2···H52.8200H16···H20A2.3100
C4···H20Cvi2.9800H16···H20C2.2900
C5···H22.8200H18···O111.7700
C5···H20Cvi2.9100H18···C12.3700
C6···H20Cvi2.9600H20A···C162.7300
C7···H20Cvi3.0900H20A···H162.3100
C10···H8vii2.9800H20C···C162.7300
C12···H10Aiii2.8600H20C···H162.2900
C13···H22.7100H20C···C4ix2.9800
C16···H20A2.7300H20C···C5ix2.9100
C16···H20C2.7300H20C···C6ix2.9600
C17···H10Aiii2.9200H20C···C7ix3.0900
C20···H162.5000
C15—O19—C20118.1 (2)C3—C2—H2119.00
C17—O18—H18109.00C2—C3—H3116.00
O11—C1—C2118.5 (3)C4—C3—H3116.00
O11—C1—C12119.9 (2)C4—C5—H5120.00
C2—C1—C12121.5 (2)C6—C5—H5120.00
C1—C2—C3121.1 (3)C5—C6—H6119.00
C2—C3—C4128.9 (3)C7—C6—H6119.00
C3—C4—C9118.9 (3)C7—C8—H8119.00
C5—C4—C9117.5 (3)C9—C8—H8119.00
C3—C4—C5123.6 (3)C4—C9—H9119.00
C4—C5—C6120.3 (3)C8—C9—H9119.00
C5—C6—C7121.9 (3)C7—C10—H10A110.00
C6—C7—C8117.4 (3)C7—C10—H10B109.00
C6—C7—C10121.3 (3)C7—C10—H10C109.00
C8—C7—C10121.4 (3)H10A—C10—H10B109.00
C7—C8—C9121.3 (3)H10A—C10—H10C109.00
C4—C9—C8121.6 (3)H10B—C10—H10C109.00
C1—C12—C13123.4 (2)C12—C13—H13119.00
C1—C12—C17120.2 (2)C14—C13—H13119.00
C13—C12—C17116.4 (2)C13—C14—H14120.00
C12—C13—C14122.5 (2)C15—C14—H14120.00
C13—C14—C15119.8 (2)C15—C16—H16120.00
O19—C15—C16124.1 (3)C17—C16—H16120.00
C14—C15—C16119.9 (3)O19—C20—H20A109.00
O19—C15—C14116.0 (3)O19—C20—H20B109.00
C15—C16—C17119.3 (2)O19—C20—H20C110.00
O18—C17—C16117.0 (2)H20A—C20—H20B109.00
C12—C17—C16122.1 (2)H20A—C20—H20C110.00
O18—C17—C12120.9 (3)H20B—C20—H20C109.00
C1—C2—H2119.00
C20—O19—C15—C16−1.9 (4)C5—C6—C7—C10178.6 (3)
C20—O19—C15—C14178.8 (3)C10—C7—C8—C9−178.8 (3)
C12—C1—C2—C3168.4 (3)C6—C7—C8—C91.5 (4)
O11—C1—C12—C13176.6 (3)C7—C8—C9—C40.9 (4)
C2—C1—C12—C13−2.5 (4)C17—C12—C13—C140.2 (4)
C2—C1—C12—C17179.3 (3)C1—C12—C13—C14−178.0 (3)
O11—C1—C12—C17−1.7 (4)C13—C12—C17—O18−178.0 (2)
O11—C1—C2—C3−10.7 (4)C13—C12—C17—C160.4 (4)
C1—C2—C3—C4179.5 (2)C1—C12—C17—O180.4 (4)
C2—C3—C4—C9−176.0 (3)C1—C12—C17—C16178.8 (3)
C2—C3—C4—C54.5 (4)C12—C13—C14—C15−0.9 (4)
C3—C4—C5—C6−177.9 (3)C13—C14—C15—C160.8 (4)
C5—C4—C9—C8−2.9 (4)C13—C14—C15—O19−179.9 (3)
C9—C4—C5—C62.6 (4)O19—C15—C16—C17−179.4 (3)
C3—C4—C9—C8177.6 (3)C14—C15—C16—C17−0.2 (4)
C4—C5—C6—C7−0.4 (4)C15—C16—C17—O18178.0 (3)
C5—C6—C7—C8−1.7 (4)C15—C16—C17—C12−0.5 (4)
D—H···AD—HH···AD···AD—H···A
O18—H18···O110.821.772.502 (3)148
C3—H3···O110.932.392.758 (3)103
C13—H13···O18v0.932.563.282 (3)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O18—H18⋯O110.821.772.502 (3)148
C13—H13⋯O18i0.932.563.282 (3)135

Symmetry code: (i) .

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3.  A short history of SHELX.

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4.  Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety.

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5.  Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines.

Authors:  Lea Barfod; Kåre Kemp; Majbritt Hansen; Arsalan Kharazmi
Journal:  Int Immunopharmacol       Date:  2002-03       Impact factor: 4.932

6.  1-(2-Hydr-oxy-5-methyl-phen-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one.

Authors:  G B Thippeswamy; D Vijay Kumar; B S Jayashree; M A Sridhar; J Shashidhara Prasad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-19

7.  Synthesis and anti-inflammatory effect of chalcones.

Authors:  H K Hsieh; L T Tsao; J P Wang; C N Lin
Journal:  J Pharm Pharmacol       Date:  2000-02       Impact factor: 3.765

Review 8.  Chemistry and pharmacology of oxyprenylated secondary plant metabolites.

Authors:  Francesco Epifano; Salvatore Genovese; Luigi Menghini; Massimo Curini
Journal:  Phytochemistry       Date:  2007-03-06       Impact factor: 4.072

9.  Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines.

Authors:  M Satyanarayana; Priti Tiwari; Brajendra K Tripathi; A K Srivastava; Ram Pratap
Journal:  Bioorg Med Chem       Date:  2004-03-01       Impact factor: 3.641

10.  Structure validation in chemical crystallography.

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1.  1-(2-Hy-droxy-5-methyl-phen-yl)-3-(2-methyl-phen-yl)prop-2-en-1-one.

Authors:  D Vijay Kumar; G B Thippeswamy; B S Jayashree; M A Sridhar
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  1 in total

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