1-(4-Amino­phen­yl)-3-[2-(trifluoro­meth­yl)phen­yl]prop-2-en-1-one

Peng, J.; Xu, H.; Li, Z.; Zhang, Y.; Wu, J.

doi:10.1107/S1600536810014169

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1156-o1157

https://doi.org/10.1107/S1600536810014169

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1-(4-Aminophenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one

Jing Peng,^a Huifen Xu,^a Zhe Li,^b Yuyan Zhang ^a and Jianzhang Wu ^a,^c ^*

^aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, ^bLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and ^cInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China
^*Correspondence e-mail: wujianzhang6@163.com,wzmcwjz@163.com

(Received 5 April 2010; accepted 17 April 2010; online 24 April 2010)

The title compound, C₁₆H₁₂F₃NO, 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 molecule adopts an E configuration about the central olefinic bond. The crystal structure is stabilized by intermolecular N—H⋯O and N—H⋯N hydrogen bonds.

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_r = 291.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.185
S = 1.00
2360 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810014169/zq2037sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014169/zq2037Isup2.hkl

checkCIF report

Comment top

Chalcones, which are open-chain flavonoids, distribute widespread in fruits, vegetables and so on. Chalcone and their derivatives are obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. They are important intermediate of organic synthesis. Due to their significant biological activities such as anti-inflammatory, antibacterial, antiangiogenic, antitumor and analgesic, they have attracted more and more attention (Heidari et al., 2009; Nielsen et al., 2005; Mojzis et al., 2008; Achanta et al., 2006; Dimmock et al., 1999). The molecule of chalcone possess two phenyl rings and one –CH=CH–C(=O)– central part. The carbonyl functional group which is responsible for the antibacterial activity of these compounds is the main feature of chalcone derivatives (Suwunwong et al., 2009).

Due to the broad spectrum of biological activities of this type of compounds, various chalcone analogues have been synthesized in order to filter the better ones or the unique ones (Narender et al., 2007; Kamal et al., 2008). As a continuation of our broad program of work on the synthesis and structural study of chalcones, the title chalcone derivative has been obtained and an X-ray diffraction study was carried out.

The molecule is approximately planar and the dihedral angle between the two phenyl rings is 10.9 (1)°. The H atoms of the central propenone group are trans to each other. The average value of the phenyl bond distances [1.385 (5) Å] and bond angles [120.7 (4)°] have normal values which agree quite well with the values reported in the literature for some analogous structures (Wu et al., 2009; Low et al., 2002; Yathirajan et al., 2006). The crystal structure is stabilized by intermolecular N(1)–H1A···O(1) and N(1)–H1B···N(1) hydrogen bonds.

Related literature top

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 top

1-(4-aminophenyl)ethanone (5 mmol) was dissolved in ethanol (10 ml) and a solution of KOH (40%, 5 drops) was added. The flask was immersed in bath of crushed ice and a solution of 2-(trifluoromethyl)benzaldehyde (5 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 24 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel (yield: 68%). Single crystals of the title compound were grown in a CH₂Cl₂/CH₃OH mixture (7:3 v/v) by slow evaporation at 277 K.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius.

1-(4-Aminophenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one top

Crystal data top

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

Data collection top

Bruker APEXII CCD area-detector diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1700 reflections with I > 2σ(I)
Graphite monochromator	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 top

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)

Crystal data top

C₁₆H₁₂F₃NO	V = 1342.7 (4) Å³
M_r = 291.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.835 (3) Å	µ = 0.12 mm⁻¹
b = 4.7866 (8) Å	T = 273 K
c = 15.177 (3) Å	0.43 × 0.28 × 0.22 mm
β = 101.108 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2360 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1700 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.974	R_int = 0.130
6607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
2360 reflections	Δρ_min = −0.25 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂F₃NO
M_r	291.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	18.835 (3), 4.7866 (8), 15.177 (3)
β (°)	101.108 (3)
V (Å³)	1342.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.951, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	6607, 2360, 1700
R_int	0.130
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.185, 1.00
No. of reflections	2360
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1ⁱ	0.86	2.42	3.235 (3)	157.5
N1—H1B···O1ⁱⁱ	0.86	2.45	3.162 (3)	140.4

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

This work was supported by the Zhejiang Province Extremely Key Subject Building Funding (Pharmacology and Biochemical Pharmaceutics 2008), the Department of Education of Zhejiang Province (No. 20070907) and the Wenzhou Administration of Science and Technology project (No. Y20080016).

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