Literature DB >> 21578397

1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Jianzhang Wu, Li Zhang, Jing Wang, Shulin Yang, Xiaokun Li.

Abstract

In the title compound, C(18)H(18)O(4), a derivative of biologically active chalcones, the dihedral angle between the two rings is 7.43 (7)°. The molecule adopts an E configuration about the central olefinic bonds. In the crystal, there are no strong inter-actions between the mol-ecules.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21578397 PMCID： PMC2971044 DOI： 10.1107/S1600536809041877

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

Related literature

For related structures, see: Subbiah Pandi et al. (2003 ▶); Low et al. (2002 ▶); Yathirajan et al. (2006 ▶); Suwunwong et al. (2009 ▶); Jasinski et al. (2009 ▶). For background to and applications of chalcones, see: Dimmock et al. (1999 ▶); Sivakumar et al. (2009 ▶); Echeverria et al. (2009 ▶); Kontogiorgis et al. (2008 ▶); Dominguez et al. (2005 ▶); Nowakowska (2007 ▶).

Experimental

Crystal data

C18H18O4 M = 298.32 Monoclinic, a = 9.0052 (10) Å b = 14.9245 (17) Å c = 11.7658 (14) Å β = 104.315 (2)° V = 1532.2 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 273 K 0.12 × 0.10 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.996 7895 measured reflections 2701 independent reflections 2125 reflections with I > 2σ(I) R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.132 S = 1.00 2701 reflections 203 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.16 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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/S1600536809041877/wn2350sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041877/wn2350Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₈O₄	F(000) = 632
M_r = 298.32	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3499 reflections
a = 9.0052 (10) Å	θ = 2.7–27.9°
b = 14.9245 (17) Å	µ = 0.09 mm⁻¹
c = 11.7658 (14) Å	T = 273 K
β = 104.315 (2)°	Block, colorless
V = 1532.2 (3) Å³	0.12 × 0.10 × 0.05 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2701 independent reflections
Radiation source: fine-focus sealed tube	2125 reflections with I > 2σ(I)
graphite	R_int = 0.044
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.989, T_max = 0.996	k = −17→15
7895 measured reflections	l = −13→13

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0938P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2701 reflections	Δρ_max = 0.14 e Å⁻³
203 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.353 (18)

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	U_iso*/U_eq
C1	0.9745 (2)	−0.05689 (12)	0.14050 (16)	0.0745 (5)
H1A	1.0183	−0.0376	0.2196	0.112*
H1B	1.0548	−0.0662	0.1012	0.112*
H1C	0.9196	−0.1119	0.1415	0.112*
C2	0.65289 (18)	−0.07567 (10)	0.42207 (13)	0.0599 (4)
H2A	0.6579	−0.1285	0.3765	0.090*
H2B	0.6153	−0.0913	0.4890	0.090*
H2C	0.7534	−0.0500	0.4479	0.090*
C3	0.44257 (19)	0.21153 (10)	−0.08152 (13)	0.0619 (4)
H3A	0.5373	0.2441	−0.0605	0.093*
H3B	0.3608	0.2517	−0.1166	0.093*
H3C	0.4499	0.1652	−0.1364	0.093*
C4	0.74716 (15)	0.02951 (9)	0.11985 (12)	0.0466 (4)
C5	0.72022 (14)	−0.00525 (9)	0.22193 (11)	0.0462 (4)
H5	0.7898	−0.0443	0.2687	0.055*
C6	0.58735 (14)	0.01944 (9)	0.25291 (11)	0.0424 (4)
C7	0.47895 (14)	0.07868 (8)	0.18520 (11)	0.0407 (4)
C8	0.51526 (15)	0.11331 (9)	0.08332 (11)	0.0437 (4)
C9	0.64562 (16)	0.08890 (9)	0.05100 (12)	0.0483 (4)
H9	0.6658	0.1122	−0.0170	0.058*
C10	0.34214 (15)	0.10052 (9)	0.22290 (12)	0.0456 (4)
H10	0.3369	0.0743	0.2935	0.055*
C11	0.22244 (15)	0.15177 (10)	0.17373 (12)	0.0509 (4)
H11	0.2175	0.1775	0.1009	0.061*
C12	0.09861 (15)	0.16858 (10)	0.23113 (12)	0.0512 (4)
C13	−0.02269 (14)	0.23528 (9)	0.17775 (12)	0.0469 (4)
C14	−0.01819 (17)	0.28712 (10)	0.08031 (13)	0.0557 (4)
H14	0.0600	0.2784	0.0426	0.067*
C15	−0.12880 (19)	0.35148 (11)	0.03909 (15)	0.0658 (5)
H15	−0.1239	0.3863	−0.0255	0.079*
C16	−0.24600 (18)	0.36410 (12)	0.09338 (15)	0.0665 (5)
H16	−0.3197	0.4079	0.0661	0.080*
C17	−0.25405 (17)	0.31221 (12)	0.18758 (15)	0.0650 (5)
H17	−0.3346	0.3200	0.2232	0.078*
C18	−0.14374 (16)	0.24862 (11)	0.22991 (13)	0.0568 (4)
H18	−0.1501	0.2141	0.2943	0.068*
O1	0.09525 (13)	0.13297 (9)	0.32420 (10)	0.0788 (4)
O2	0.41260 (11)	0.17261 (7)	0.02032 (8)	0.0580 (3)
O3	0.87208 (11)	0.01000 (7)	0.08015 (9)	0.0645 (4)
O4	0.55259 (11)	−0.01253 (7)	0.35229 (9)	0.0568 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0661 (10)	0.0857 (12)	0.0833 (11)	0.0327 (9)	0.0404 (9)	0.0290 (10)
C2	0.0601 (9)	0.0681 (10)	0.0523 (9)	0.0107 (8)	0.0156 (7)	0.0195 (7)
C3	0.0716 (10)	0.0603 (10)	0.0518 (9)	0.0047 (8)	0.0115 (8)	0.0158 (7)
C4	0.0438 (7)	0.0485 (8)	0.0512 (8)	0.0025 (6)	0.0186 (6)	0.0020 (6)
C5	0.0450 (8)	0.0464 (8)	0.0483 (8)	0.0063 (6)	0.0137 (6)	0.0071 (6)
C6	0.0441 (7)	0.0449 (7)	0.0390 (7)	−0.0012 (6)	0.0119 (6)	0.0025 (6)
C7	0.0407 (7)	0.0426 (7)	0.0384 (7)	0.0006 (5)	0.0088 (5)	−0.0029 (5)
C8	0.0455 (8)	0.0414 (7)	0.0421 (7)	0.0021 (6)	0.0067 (6)	0.0006 (6)
C9	0.0540 (8)	0.0510 (8)	0.0423 (8)	0.0014 (6)	0.0164 (6)	0.0065 (6)
C10	0.0455 (8)	0.0499 (8)	0.0409 (7)	0.0007 (6)	0.0097 (6)	−0.0048 (6)
C11	0.0463 (8)	0.0626 (9)	0.0430 (8)	0.0072 (6)	0.0097 (6)	−0.0019 (6)
C12	0.0445 (8)	0.0646 (9)	0.0433 (8)	0.0024 (7)	0.0086 (6)	−0.0059 (7)
C13	0.0392 (7)	0.0536 (8)	0.0460 (8)	−0.0003 (6)	0.0071 (6)	−0.0107 (6)
C14	0.0504 (8)	0.0632 (9)	0.0559 (9)	0.0055 (7)	0.0174 (7)	−0.0042 (7)
C15	0.0666 (10)	0.0660 (10)	0.0647 (10)	0.0118 (8)	0.0159 (8)	0.0051 (8)
C16	0.0532 (9)	0.0684 (11)	0.0751 (11)	0.0148 (8)	0.0107 (8)	−0.0029 (9)
C17	0.0444 (8)	0.0741 (11)	0.0801 (12)	0.0072 (7)	0.0221 (8)	−0.0086 (9)
C18	0.0496 (8)	0.0657 (9)	0.0580 (9)	−0.0010 (7)	0.0188 (7)	−0.0053 (7)
O1	0.0688 (8)	0.1132 (10)	0.0602 (7)	0.0294 (7)	0.0272 (6)	0.0240 (7)
O2	0.0577 (6)	0.0647 (7)	0.0522 (6)	0.0165 (5)	0.0150 (5)	0.0177 (5)
O3	0.0587 (7)	0.0769 (8)	0.0675 (7)	0.0206 (5)	0.0340 (6)	0.0224 (5)
O4	0.0533 (6)	0.0719 (7)	0.0500 (6)	0.0154 (5)	0.0216 (5)	0.0200 (5)

C1—O3	1.4241 (17)	C8—O2	1.3596 (15)
C1—H1A	0.9600	C8—C9	1.3697 (19)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.3317 (19)
C2—O4	1.4182 (16)	C10—H10	0.9300
C2—H2A	0.9600	C11—C12	1.4611 (19)
C2—H2B	0.9600	C11—H11	0.9300
C2—H2C	0.9600	C12—O1	1.2244 (17)
C3—O2	1.4163 (17)	C12—C13	1.496 (2)
C3—H3A	0.9600	C13—C18	1.391 (2)
C3—H3B	0.9600	C13—C14	1.392 (2)
C3—H3C	0.9600	C14—C15	1.382 (2)
C4—O3	1.3521 (16)	C14—H14	0.9300
C4—C9	1.3827 (19)	C15—C16	1.375 (2)
C4—C5	1.3836 (19)	C15—H15	0.9300
C5—C6	1.3842 (17)	C16—C17	1.369 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—O4	1.3688 (15)	C17—C18	1.375 (2)
C6—C7	1.4088 (18)	C17—H17	0.9300
C7—C8	1.4158 (18)	C18—H18	0.9300
C7—C10	1.4461 (18)

O3—C1—H1A	109.5	C8—C9—C4	119.73 (12)
O3—C1—H1B	109.5	C8—C9—H9	120.1
H1A—C1—H1B	109.5	C4—C9—H9	120.1
O3—C1—H1C	109.5	C11—C10—C7	130.97 (13)
H1A—C1—H1C	109.5	C11—C10—H10	114.5
H1B—C1—H1C	109.5	C7—C10—H10	114.5
O4—C2—H2A	109.5	C10—C11—C12	121.74 (13)
O4—C2—H2B	109.5	C10—C11—H11	119.1
H2A—C2—H2B	109.5	C12—C11—H11	119.1
O4—C2—H2C	109.5	O1—C12—C11	121.96 (13)
H2A—C2—H2C	109.5	O1—C12—C13	119.16 (13)
H2B—C2—H2C	109.5	C11—C12—C13	118.79 (13)
O2—C3—H3A	109.5	C18—C13—C14	117.99 (13)
O2—C3—H3B	109.5	C18—C13—C12	118.71 (13)
H3A—C3—H3B	109.5	C14—C13—C12	123.26 (12)
O2—C3—H3C	109.5	C15—C14—C13	120.66 (14)
H3A—C3—H3C	109.5	C15—C14—H14	119.7
H3B—C3—H3C	109.5	C13—C14—H14	119.7
O3—C4—C9	114.95 (12)	C14—C15—C16	120.09 (16)
O3—C4—C5	123.95 (12)	C14—C15—H15	120.0
C9—C4—C5	121.09 (12)	C16—C15—H15	120.0
C6—C5—C4	118.50 (12)	C15—C16—C17	119.95 (15)
C6—C5—H5	120.7	C15—C16—H16	120.0
C4—C5—H5	120.7	C17—C16—H16	120.0
O4—C6—C5	121.82 (11)	C16—C17—C18	120.38 (14)
O4—C6—C7	115.41 (11)	C16—C17—H17	119.8
C5—C6—C7	122.77 (11)	C18—C17—H17	119.8
C6—C7—C8	115.79 (11)	C13—C18—C17	120.91 (15)
C6—C7—C10	119.45 (11)	C13—C18—H18	119.6
C8—C7—C10	124.75 (12)	C17—C18—H18	119.5
O2—C8—C9	122.39 (12)	C8—O2—C3	118.82 (11)
O2—C8—C7	115.53 (11)	C4—O3—C1	118.07 (11)
C9—C8—C7	122.08 (12)	C6—O4—C2	118.61 (10)

10 in total

Review 1. Bioactivities of chalcones.

Authors: J R Dimmock; D W Elias; M A Beazely; N M Kandepu
Journal: Curr Med Chem Date: 1999-12 Impact factor: 4.530

Review 2. A review of anti-infective and anti-inflammatory chalcones.

Authors: Zdzisława Nowakowska
Journal: Eur J Med Chem Date: 2006-11-15 Impact factor: 6.514

3. Synthesis and antimalarial activity of sulfonamide chalcone derivatives.

Authors: José N Domínguez; Caritza León; Juan Rodrigues; Neira Gamboa de Domínguez; Jiri Gut; Philip J Rosenthal
Journal: Farmaco Date: 2005-04

4. A short history of SHELX.

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

Review 5. Chalcones and their potential role in inflammation.

Authors: C Kontogiorgis; M Mantzanidou; D Hadjipavlou-Litina
Journal: Mini Rev Med Chem Date: 2008-10 Impact factor: 3.862

6. Antifungal activity, mechanism and QSAR studies on chalcones.

Authors: Ponnurengam Malliappan Sivakumar; Thangavelu Muthu Kumar; Mukesh Doble
Journal: Chem Biol Drug Des Date: 2009-07 Impact factor: 2.817

7. A comparison of the supramolecular structures of 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(N,N-dimethylamino)phenyl]prop-2-en-1-one.

Authors: John N Low; Justo Cobo; Manuel Nogueras; Adolfo Sánchez; Andrea Albornoz; Rodrigo Abonia
Journal: Acta Crystallogr C Date: 2001-12-22 Impact factor: 1.172

8. (E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Authors: Thitipone Suwunwong; Suchada Chantrapromma; Paradorn Pakdeevanich; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-06-13

9. 1-(2-Hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one.

Authors: A Subbiah Pandi; D Velmurugan; S Shanmuga Sundara Raj; Hoong Kun Fun; M C Bansal
Journal: Acta Crystallogr C Date: 2003-05-10 Impact factor: 1.172

10. Structural antitumoral activity relationships of synthetic chalcones.

Authors: Cesar Echeverria; Juan Francisco Santibañez; Oscar Donoso-Tauda; Carlos A Escobar; Rodrigo Ramirez-Tagle
Journal: Int J Mol Sci Date: 2009-01-09 Impact factor: 6.208