Literature DB >> 22199706

(E)-3-(Furan-2-yl)-1-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Kamini Kapoor, Vivek K Gupta, Rajni Kant, Jalpa R Pandya, Sunil B Lade, Hitendra S Joshi.

Abstract

In the title mol-ecule, C(14)H(12)O(3), the prop-2-en-1-one unit forms dihedral angles of 12.96 (5) and 7.89 (7)° with the 4-meth-oxy-phenyl group and the furan ring, respectively. The furan and benzene rings form a dihedral angle of 8.56 (5)°. In the crystal, C-H⋯π and π-π inter-actions are observed between the benzene and heterocyclic rings [centroid-centroid distance = 3.760 (1) Å].

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 22199706 PMCID： PMC3238853 DOI： 10.1107/S160053681104373X

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

Related literature

For biological properties of chalcone derivatives, see: Hsieh et al. (1998 ▶); Anto et al. (1994 ▶); Bhat et al. (2005 ▶); Xue et al. (2004 ▶). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 ▶); Dimmock et al. (1998 ▶). For related structures, see: Fun et al. (2008 ▶); Guo et al. (2008 ▶).

Experimental

Crystal data

C14H12O3 M = 228.24 Monoclinic, a = 7.1583 (3) Å b = 19.1516 (8) Å c = 8.4293 (3) Å β = 94.357 (4)° V = 1152.26 (8) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.976, T max = 1.000 13386 measured reflections 2027 independent reflections 1546 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.096 S = 1.03 2027 reflections 156 parameters H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.13 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104373X/gk2411sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104373X/gk2411Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681104373X/gk2411Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₂O₃	F(000) = 480
M_r = 228.24	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 341 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1583 (3) Å	Cell parameters from 5366 reflections
b = 19.1516 (8) Å	θ = 3.6–29.0°
c = 8.4293 (3) Å	µ = 0.09 mm⁻¹
β = 94.357 (4)°	T = 293 K
V = 1152.26 (8) Å³	Block, yellow
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur S diffractometer	2027 independent reflections
Radiation source: fine-focus sealed tube	1546 reflections with I > 2σ(I)
graphite	R_int = 0.028
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −22→22
T_min = 0.976, T_max = 1.000	l = −10→10
13386 measured reflections

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) = 0.096	w = 1/[σ²(F_o²) + (0.0349P)² + 0.2369P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2027 reflections	Δρ_max = 0.13 e Å⁻³
156 parameters	Δρ_min = −0.13 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: 0.0089 (17)

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	0.5604 (2)	0.90359 (8)	−0.00421 (19)	0.0538 (4)
C2	0.3963 (2)	0.85830 (8)	0.01140 (19)	0.0553 (4)
H2	0.3954	0.8290	0.0993	0.066*
C3	0.2496 (2)	0.85775 (8)	−0.09527 (19)	0.0548 (4)
H3	0.2546	0.8877	−0.1818	0.066*
C4	0.0853 (2)	0.81579 (8)	−0.09015 (19)	0.0543 (4)
C6	−0.0871 (3)	0.73468 (11)	0.0068 (2)	0.0783 (6)
H6	−0.1271	0.6994	0.0720	0.094*
C7	−0.1863 (3)	0.75916 (11)	−0.1198 (2)	0.0774 (6)
H7	−0.3048	0.7446	−0.1591	0.093*
C8	−0.0767 (2)	0.81144 (10)	−0.1830 (2)	0.0701 (5)
H8	−0.1095	0.8383	−0.2727	0.084*
C9	0.7104 (2)	0.90560 (8)	0.12703 (18)	0.0481 (4)
C10	0.7260 (2)	0.85704 (8)	0.24994 (19)	0.0545 (4)
H10	0.6348	0.8227	0.2552	0.065*
C11	0.8739 (2)	0.85887 (8)	0.3638 (2)	0.0581 (4)
H11	0.8827	0.8254	0.4440	0.070*
C12	1.0100 (2)	0.91016 (8)	0.36004 (19)	0.0519 (4)
C13	0.9963 (2)	0.95944 (8)	0.2403 (2)	0.0582 (4)
H13	1.0863	0.9943	0.2365	0.070*
C14	0.8480 (2)	0.95650 (8)	0.1263 (2)	0.0571 (4)
H14	0.8399	0.9899	0.0460	0.068*
C17	1.3024 (2)	0.95549 (10)	0.4718 (2)	0.0740 (5)
H17A	1.3600	0.9490	0.3737	0.111*
H17B	1.3931	0.9471	0.5596	0.111*
H17C	1.2567	1.0025	0.4773	0.111*
O5	0.08105 (16)	0.76778 (6)	0.02948 (13)	0.0675 (4)
O15	0.57315 (17)	0.93872 (7)	−0.12483 (15)	0.0750 (4)
O16	1.14981 (16)	0.90766 (6)	0.47907 (14)	0.0687 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0570 (10)	0.0505 (9)	0.0550 (10)	0.0044 (8)	0.0116 (8)	0.0056 (8)
C2	0.0572 (10)	0.0542 (10)	0.0547 (10)	−0.0003 (8)	0.0049 (8)	0.0055 (8)
C3	0.0612 (10)	0.0509 (9)	0.0527 (9)	0.0065 (8)	0.0076 (8)	−0.0005 (8)
C4	0.0568 (10)	0.0557 (10)	0.0503 (9)	0.0069 (8)	0.0032 (7)	−0.0081 (8)
C6	0.0736 (13)	0.0847 (14)	0.0782 (13)	−0.0259 (11)	0.0153 (10)	−0.0189 (11)
C7	0.0565 (11)	0.0969 (15)	0.0789 (14)	−0.0069 (11)	0.0047 (10)	−0.0358 (12)
C8	0.0661 (12)	0.0820 (13)	0.0605 (11)	0.0119 (10)	−0.0062 (9)	−0.0151 (10)
C9	0.0499 (9)	0.0438 (8)	0.0519 (9)	0.0006 (7)	0.0129 (7)	0.0024 (7)
C10	0.0534 (9)	0.0495 (9)	0.0609 (10)	−0.0112 (7)	0.0077 (8)	0.0065 (8)
C11	0.0611 (10)	0.0533 (10)	0.0596 (10)	−0.0100 (8)	0.0024 (8)	0.0121 (8)
C12	0.0513 (9)	0.0496 (9)	0.0554 (10)	−0.0028 (7)	0.0089 (7)	−0.0027 (8)
C13	0.0574 (10)	0.0506 (10)	0.0675 (11)	−0.0128 (8)	0.0112 (8)	0.0023 (8)
C14	0.0622 (10)	0.0494 (9)	0.0609 (10)	−0.0050 (8)	0.0126 (8)	0.0119 (8)
C17	0.0587 (11)	0.0759 (12)	0.0871 (14)	−0.0184 (9)	0.0024 (9)	−0.0030 (11)
O5	0.0650 (8)	0.0726 (8)	0.0642 (8)	−0.0123 (6)	−0.0009 (6)	−0.0002 (6)
O15	0.0731 (8)	0.0854 (9)	0.0663 (8)	−0.0068 (7)	0.0035 (6)	0.0267 (7)
O16	0.0625 (7)	0.0702 (8)	0.0717 (8)	−0.0168 (6)	−0.0055 (6)	0.0065 (6)

C1—O15	1.2284 (18)	C9—C14	1.386 (2)
C1—C2	1.474 (2)	C9—C10	1.390 (2)
C1—C9	1.483 (2)	C10—C11	1.374 (2)
C2—C3	1.330 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.385 (2)
C3—C4	1.428 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—O16	1.3633 (18)
C4—C8	1.351 (2)	C12—C13	1.380 (2)
C4—O5	1.3667 (19)	C13—C14	1.378 (2)
C6—C7	1.322 (3)	C13—H13	0.9300
C6—O5	1.361 (2)	C14—H14	0.9300
C6—H6	0.9300	C17—O16	1.4307 (19)
C7—C8	1.402 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600

O15—C1—C2	120.42 (15)	C11—C10—C9	121.16 (14)
O15—C1—C9	120.53 (15)	C11—C10—H10	119.4
C2—C1—C9	119.05 (14)	C9—C10—H10	119.4
C3—C2—C1	122.54 (15)	C10—C11—C12	120.51 (15)
C3—C2—H2	118.7	C10—C11—H11	119.7
C1—C2—H2	118.7	C12—C11—H11	119.7
C2—C3—C4	126.45 (15)	O16—C12—C13	124.72 (14)
C2—C3—H3	116.8	O16—C12—C11	115.88 (14)
C4—C3—H3	116.8	C13—C12—C11	119.40 (15)
C8—C4—O5	108.66 (15)	C14—C13—C12	119.35 (15)
C8—C4—C3	133.60 (17)	C14—C13—H13	120.3
O5—C4—C3	117.73 (13)	C12—C13—H13	120.3
C7—C6—O5	111.29 (18)	C13—C14—C9	122.40 (15)
C7—C6—H6	124.4	C13—C14—H14	118.8
O5—C6—H6	124.4	C9—C14—H14	118.8
C6—C7—C8	106.16 (17)	O16—C17—H17A	109.5
C6—C7—H7	126.9	O16—C17—H17B	109.5
C8—C7—H7	126.9	H17A—C17—H17B	109.5
C4—C8—C7	107.71 (18)	O16—C17—H17C	109.5
C4—C8—H8	126.1	H17A—C17—H17C	109.5
C7—C8—H8	126.1	H17B—C17—H17C	109.5
C14—C9—C10	117.17 (15)	C6—O5—C4	106.19 (14)
C14—C9—C1	119.32 (14)	C12—O16—C17	117.81 (13)
C10—C9—C1	123.45 (14)

O15—C1—C2—C3	−5.9 (2)	C1—C9—C10—C11	176.21 (15)
C9—C1—C2—C3	174.64 (15)	C9—C10—C11—C12	1.1 (3)
C1—C2—C3—C4	179.95 (14)	C10—C11—C12—O16	179.49 (15)
C2—C3—C4—C8	176.35 (18)	C10—C11—C12—C13	−0.3 (2)
C2—C3—C4—O5	−4.8 (2)	O16—C12—C13—C14	179.98 (15)
O5—C6—C7—C8	−0.2 (2)	C11—C12—C13—C14	−0.3 (2)
O5—C4—C8—C7	0.07 (19)	C12—C13—C14—C9	0.1 (2)
C3—C4—C8—C7	179.02 (17)	C10—C9—C14—C13	0.7 (2)
C6—C7—C8—C4	0.1 (2)	C1—C9—C14—C13	−176.87 (15)
O15—C1—C9—C14	11.8 (2)	C7—C6—O5—C4	0.3 (2)
C2—C1—C9—C14	−168.82 (13)	C8—C4—O5—C6	−0.21 (18)
O15—C1—C9—C10	−165.65 (15)	C3—C4—O5—C6	−179.35 (14)
C2—C1—C9—C10	13.8 (2)	C13—C12—O16—C17	−6.0 (2)
C14—C9—C10—C11	−1.2 (2)	C11—C12—O16—C17	174.30 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.93	2.76	3.592 (2)	149
C17—H17C···Cg2ⁱⁱ	0.96	3.07	3.788 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.93	2.76	3.592 (2)	149

Symmetry code: (i) .

9 in total

1. 3D QSAR studies on antimalarial alkoxylated and hydroxylated chalcones by CoMFA and CoMSIA.

Authors: C X Xue; S Y Cui; M C Liu; Z D Hu; B T Fan
Journal: Eur J Med Chem Date: 2004-09 Impact factor: 6.514

2. Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents.

Authors: B A Bhat; K L Dhar; S C Puri; A K Saxena; M Shanmugavel; G N Qazi
Journal: Bioorg Med Chem Lett Date: 2005-06-15 Impact factor: 2.823

3. A short history of SHELX.

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

4. Synthesis and anti-inflammatory effect of chalcones and related compounds.

Authors: H K Hsieh; T H Lee; J P Wang; J J Wang; C N Lin
Journal: Pharm Res Date: 1998-01 Impact factor: 4.200

5. In vitro evaluation of newly developed chalcone analogues in human cancer cells.

Authors: R De Vincenzo; C Ferlini; M Distefano; C Gaggini; A Riva; E Bombardelli; P Morazzoni; P Valenti; F Belluti; F O Ranelletti; S Mancuso; G Scambia
Journal: Cancer Chemother Pharmacol Date: 2000 Impact factor: 3.333

6. Cytotoxic activities of Mannich bases of chalcones and related compounds.

Authors: J R Dimmock; N M Kandepu; M Hetherington; J W Quail; U Pugazhenthi; A M Sudom; M Chamankhah; P Rose; E Pass; T M Allen; S Halleran; J Szydlowski; B Mutus; M Tannous; E K Manavathu; T G Myers; E De Clercq; J Balzarini
Journal: J Med Chem Date: 1998-03-26 Impact factor: 7.446