Literature DB >> 21579201

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

Jing Peng, Huifen Xu, Zhe Li, Yuyan Zhang, Jianzhang Wu.

Abstract

The title compound, C(16)H(12)F(3)NO, a derivative of biologically active chalcones, comprises two benzene rings and a central -CH=CH-C(=O)- unit. The dihedral angle between the two rings is 10.9 (1)° and the mol-ecule adopts an E configuration about the central olefinic bond. The crystal structure is stabilized by inter-molecular N-H⋯O and N-H⋯N hydrogen bonds.

Entities: CellLine Chemical Disease Gene

Year: 2010 PMID： 21579201 PMCID： PMC2979023 DOI： 10.1107/S1600536810014169

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

Related literature

For related structures, see: Narender et al. (2007 ▶); Kamal et al. (2008 ▶); Wu et al. (2009 ▶); Low et al. (2002 ▶); Yathirajan et al. (2006 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Heidari et al. (2009 ▶); Nielsen et al. (2005 ▶); Mojzis et al. (2008 ▶); Achanta et al. (2006 ▶); Dimmock et al. (1999 ▶); Liang et al. (2007a ▶,b ▶, 2009 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C16H12F3NO M = 291.27 Monoclinic, a = 18.835 (3) Å b = 4.7866 (8) Å c = 15.177 (3) Å β = 101.108 (3)° V = 1342.7 (4) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 273 K 0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.951, T max = 0.974 6607 measured reflections 2360 independent reflections 1700 reflections with I > 2σ(I) R int = 0.130

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.185 S = 1.00 2360 reflections 191 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.25 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/S1600536810014169/zq2037sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014169/zq2037Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₂F₃NO	F(000) = 600
M_r = 291.27	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1903 reflections
a = 18.835 (3) Å	θ = 2.7–25.4°
b = 4.7866 (8) Å	µ = 0.12 mm⁻¹
c = 15.177 (3) Å	T = 273 K
β = 101.108 (3)°	Block, colorless
V = 1342.7 (4) Å³	0.43 × 0.28 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1700 reflections with I > 2σ(I)
graphite	R_int = 0.130
φ and ω scans	θ_max = 25.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −21→22
T_min = 0.951, T_max = 0.974	k = −5→5
6607 measured reflections	l = −18→10

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.185	w = 1/[σ²(F_o²) + (0.1025P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2360 reflections	Δρ_max = 0.23 e Å⁻³
191 parameters	Δρ_min = −0.25 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: 0.005 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.34496 (14)	−0.3803 (5)	0.79335 (18)	0.0501 (6)
C2	0.36516 (11)	−0.4190 (5)	0.70442 (16)	0.0410 (6)
C3	0.42148 (13)	−0.6043 (6)	0.69850 (19)	0.0522 (7)
H3	0.4457	−0.6952	0.7497	0.063*
C4	0.44121 (14)	−0.6525 (6)	0.6172 (2)	0.0604 (8)
H4	0.4786	−0.7762	0.6135	0.073*
C5	0.40580 (14)	−0.5182 (6)	0.5413 (2)	0.0593 (8)
H5	0.4193	−0.5502	0.4864	0.071*
C6	0.34998 (13)	−0.3352 (6)	0.54698 (18)	0.0529 (7)
H6	0.3263	−0.2464	0.4950	0.063*
C7	0.32798 (12)	−0.2792 (5)	0.62745 (16)	0.0412 (6)
C8	0.26836 (13)	−0.0800 (5)	0.62980 (17)	0.0476 (6)
H8	0.2543	−0.0556	0.6848	0.057*
C9	0.23372 (13)	0.0641 (5)	0.56274 (18)	0.0486 (6)
H9	0.2468	0.0408	0.5072	0.058*
C10	0.17464 (12)	0.2634 (5)	0.56880 (16)	0.0416 (6)
C11	0.14526 (11)	0.4364 (4)	0.48894 (16)	0.0375 (6)
C12	0.17160 (12)	0.4283 (5)	0.40932 (17)	0.0449 (6)
H12	0.2090	0.3057	0.4046	0.054*
C13	0.14390 (12)	0.5965 (5)	0.33733 (17)	0.0469 (6)
H13	0.1628	0.5861	0.2852	0.056*
C14	0.08774 (11)	0.7824 (5)	0.34190 (16)	0.0416 (6)
C15	0.05970 (12)	0.7888 (5)	0.42057 (18)	0.0459 (6)
H15	0.0215	0.9084	0.4246	0.055*
C16	0.08779 (12)	0.6204 (5)	0.49211 (17)	0.0431 (6)
H16	0.0683	0.6286	0.5439	0.052*
F1	0.34613 (11)	−0.1107 (3)	0.81944 (11)	0.0793 (6)
F2	0.27876 (9)	−0.4720 (4)	0.79671 (12)	0.0768 (6)
F3	0.38918 (9)	−0.5133 (4)	0.86064 (11)	0.0736 (6)
N1	0.05877 (11)	0.9453 (4)	0.26847 (15)	0.0543 (6)
H1A	0.0227	1.0535	0.2707	0.065*
H1B	0.0768	0.9384	0.2206	0.065*
O1	0.15200 (10)	0.2839 (4)	0.63840 (13)	0.0660 (6)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0540 (15)	0.0454 (14)	0.0489 (15)	0.0024 (11)	0.0046 (12)	0.0064 (12)
C2	0.0363 (12)	0.0409 (12)	0.0441 (13)	−0.0044 (10)	0.0037 (10)	0.0006 (11)
C3	0.0437 (14)	0.0539 (14)	0.0552 (16)	0.0059 (11)	0.0000 (12)	0.0051 (13)
C4	0.0424 (14)	0.0695 (17)	0.0703 (19)	0.0150 (13)	0.0132 (13)	−0.0025 (15)
C5	0.0568 (16)	0.0717 (18)	0.0522 (16)	0.0089 (14)	0.0179 (14)	−0.0028 (14)
C6	0.0482 (14)	0.0662 (16)	0.0442 (14)	0.0107 (13)	0.0087 (12)	0.0049 (13)
C7	0.0352 (12)	0.0448 (13)	0.0432 (13)	−0.0002 (10)	0.0065 (10)	0.0021 (11)
C8	0.0443 (13)	0.0562 (14)	0.0439 (14)	0.0075 (11)	0.0127 (11)	0.0048 (12)
C9	0.0473 (14)	0.0549 (15)	0.0441 (14)	0.0092 (11)	0.0100 (12)	0.0055 (12)
C10	0.0351 (12)	0.0461 (13)	0.0433 (14)	−0.0020 (10)	0.0070 (10)	−0.0018 (11)
C11	0.0289 (11)	0.0391 (12)	0.0443 (13)	−0.0040 (9)	0.0063 (10)	−0.0018 (10)
C12	0.0340 (12)	0.0507 (14)	0.0508 (14)	0.0063 (10)	0.0103 (11)	−0.0009 (12)
C13	0.0407 (13)	0.0590 (15)	0.0430 (14)	0.0018 (11)	0.0130 (11)	0.0022 (12)
C14	0.0314 (11)	0.0433 (12)	0.0469 (14)	−0.0070 (9)	−0.0009 (10)	0.0021 (11)
C15	0.0352 (12)	0.0487 (13)	0.0542 (15)	0.0075 (10)	0.0093 (11)	0.0002 (12)
C16	0.0375 (12)	0.0496 (13)	0.0438 (13)	−0.0004 (10)	0.0118 (10)	−0.0019 (11)
F1	0.1293 (15)	0.0565 (10)	0.0519 (10)	0.0041 (10)	0.0173 (10)	−0.0057 (8)
F2	0.0622 (10)	0.1068 (14)	0.0678 (11)	−0.0078 (9)	0.0287 (9)	0.0063 (10)
F3	0.0831 (12)	0.0847 (12)	0.0489 (10)	0.0169 (9)	0.0029 (9)	0.0161 (8)
N1	0.0472 (12)	0.0637 (13)	0.0503 (13)	0.0050 (10)	0.0052 (10)	0.0114 (11)
O1	0.0664 (12)	0.0844 (14)	0.0514 (11)	0.0276 (10)	0.0223 (10)	0.0148 (10)

C1—F1	1.349 (3)	C9—C10	1.482 (3)
C1—F2	1.332 (3)	C9—H9	0.9300
C1—F3	1.347 (3)	C10—O1	1.217 (3)
C1—C2	1.483 (4)	C10—C11	1.484 (3)
C2—C3	1.399 (3)	C11—C16	1.404 (3)
C2—C7	1.410 (3)	C11—C12	1.392 (3)
C3—C4	1.375 (4)	C12—C13	1.376 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (4)	C13—C14	1.394 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (4)	C14—N1	1.383 (3)
C5—H5	0.9300	C14—C15	1.396 (3)
C6—C7	1.389 (3)	C15—C16	1.374 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.479 (3)	C16—H16	0.9300
C8—C9	1.296 (4)	N1—H1A	0.8600
C8—H8	0.9300	N1—H1B	0.8600

F1—C1—F2	105.4 (2)	C8—C9—C10	124.3 (2)
F1—C1—F3	104.9 (2)	C8—C9—H9	117.8
F2—C1—F3	105.2 (2)	C10—C9—H9	117.8
F1—C1—C2	113.2 (2)	O1—C10—C11	121.7 (2)
F2—C1—C2	113.6 (2)	O1—C10—C9	119.9 (2)
F3—C1—C2	113.7 (2)	C11—C10—C9	118.3 (2)
C3—C2—C7	120.6 (2)	C16—C11—C12	116.9 (2)
C3—C2—C1	117.9 (2)	C16—C11—C10	119.4 (2)
C7—C2—C1	121.4 (2)	C12—C11—C10	123.7 (2)
C4—C3—C2	120.2 (3)	C13—C12—C11	121.9 (2)
C4—C3—H3	119.9	C13—C12—H12	119.0
C2—C3—H3	119.9	C11—C12—H12	119.0
C3—C4—C5	120.1 (2)	C12—C13—C14	120.6 (2)
C3—C4—H4	119.9	C12—C13—H13	119.7
C5—C4—H4	119.9	C14—C13—H13	119.7
C6—C5—C4	119.7 (3)	N1—C14—C15	121.4 (2)
C6—C5—H5	120.1	N1—C14—C13	120.3 (2)
C4—C5—H5	120.1	C15—C14—C13	118.2 (2)
C5—C6—C7	122.4 (3)	C16—C15—C14	120.8 (2)
C5—C6—H6	118.8	C16—C15—H15	119.6
C7—C6—H6	118.8	C14—C15—H15	119.6
C6—C7—C2	116.9 (2)	C15—C16—C11	121.6 (2)
C6—C7—C8	120.1 (2)	C15—C16—H16	119.2
C2—C7—C8	123.0 (2)	C11—C16—H16	119.2
C9—C8—C7	126.4 (2)	C14—N1—H1A	120.0
C9—C8—H8	116.8	C14—N1—H1B	120.0
C7—C8—H8	116.8	H1A—N1—H1B	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1ⁱ	0.86	2.42	3.235 (3)	158
N1—H1B···O1ⁱⁱ	0.86	2.45	3.162 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N1ⁱ	0.86	2.42	3.235 (3)	158
N1—H1B⋯O1ⁱⁱ	0.86	2.45	3.162 (3)	140

Symmetry codes: (i) ; (ii) .

13 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

2. A boronic-chalcone derivative exhibits potent anticancer activity through inhibition of the proteasome.

Authors: Geetha Achanta; Aneta Modzelewska; Li Feng; Saeed R Khan; Peng Huang
Journal: Mol Pharmacol Date: 2006-04-24 Impact factor: 4.436

3. Synthesis of mono-carbonyl analogues of curcumin and their effects on inhibition of cytokine release in LPS-stimulated RAW 264.7 macrophages.

Authors: Chengguang Zhao; Ju Yang; Yi Wang; Donglou Liang; Xuyi Yang; Xiaoxia Li; Jianzhang Wu; Xiaoping Wu; Shulin Yang; Xiaokun Li; Guang Liang
Journal: Bioorg Med Chem Date: 2010-03-06 Impact factor: 3.641

4. A short history of SHELX.

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

Review 5. Antiangiogenic effects of flavonoids and chalcones.

Authors: J Mojzis; L Varinska; G Mojzisova; I Kostova; L Mirossay
Journal: Pharmacol Res Date: 2008-02-23 Impact factor: 7.658

6. 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

7. 1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Authors: Jianzhang Wu; Li Zhang; Jing Wang; Shulin Yang; Xiaokun Li
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-23

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. Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia.

Authors: T Narender; K Papi Reddy; Kumkum Srivastava; D K Mishra; S K Puri
Journal: Org Lett Date: 2007-11-22 Impact factor: 6.005

10. Solid-phase synthesis of new pyrrolobenzodiazepine-chalcone conjugates: DNA-binding affinity and anticancer activity.

Authors: Ahmed Kamal; N Shankaraiah; S Prabhakar; Ch Ratna Reddy; N Markandeya; K Laxma Reddy; V Devaiah
Journal: Bioorg Med Chem Lett Date: 2008-03-05 Impact factor: 2.823

6 in total