(E)-3-(4-Fluoro­phen­yl)-1-(2-nitro­phen­yl)prop-2-en-1-one

Pan, Z.

doi:10.1107/S160053681001809X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1414

https://doi.org/10.1107/S160053681001809X

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(E)-3-(4-Fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one

Zhi-fang Pan ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weichidu@163.com

(Received 2 May 2010; accepted 16 May 2010; online 22 May 2010)

The title compound, C₁₅H₁₀F_NO₃, was prepared from 2-nitroacetphenone and 4-fluorobenzaldehyde by an Aldol condensation reaction. The dihedral angle formed by the two benzene rings is 67.37 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O and C—H⋯F hydrogen bonds.

Related literature

For the biological activities of chalcones, see: Hsieh et al. (1998 ); Anto et al. (1994 ); De Vincenzo et al.(2000 ); Dimmock et al. (1998 ). For related structures, see: Fun et al. (2008 ); Guo et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₀FNO₃
M_r = 271.24
Monoclinic, P 2₁ /n
a = 7.7698 (16) Å
b = 17.072 (3) Å
c = 9.759 (2) Å
β = 96.72 (3)°
V = 1285.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.3 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD diffractometer
12293 measured reflections
2921 independent reflections
2218 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.141
S = 1.13
2921 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O3ⁱ	0.93	2.57	3.500 (2)	177
C5—H5A⋯F1ⁱⁱ	0.93	2.54	3.396 (2)	153
C9—H9A⋯O3ⁱⁱⁱ	0.93	2.57	3.411 (2)	150
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+2; (iii) -x, -y, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 global, I. DOI: https://doi.org/10.1107/S160053681001809X/lh5041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001809X/lh5041Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological activities which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al.,1994). Of particular interest, the effectiveness of chalcones against cancer has been investigated (De Vincenzo et al.,2000; Dimmock et al.,1998). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure herein.

In the title molecule (Fig. 1) the dihedral angle formed by the two benzene rings is 67.44 (3)°. The nitro group is twisted from the attached benzene ring forming a dihedral angle of 53.73 (5)°. All of the bond lengths and bond angles are in normal ranges and comparable to those in related structures (Fun et al.,2008; Guo et al.,2009). The crystal structure is stabilized by weak intermolecular C—H···O and C—H···F hydrogen bonds.

Related literature top

For the biological activities of chalcones, see: Hsieh et al. (1998); Anto et al. (1994); De Vincenzo et al.(2000); Dimmock et al. (1998). For related structures, see: Fun et al. (2008); Guo et al. (2009).

Experimental top

A mixture of 2-nitroacetphenone (0.02 mol), 4-fluorobenzaldehyde (0.02 mol) and 8% NaOH(5 ml) was stirred in ethanol(30 ml) for 4 h to afford the title compound (yield 65%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Structure description top

For the biological activities of chalcones, see: Hsieh et al. (1998); Anto et al. (1994); De Vincenzo et al.(2000); Dimmock et al. (1998). For related structures, see: Fun et al. (2008); Guo et al. (2009).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

(E)-3-(4-Fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀FNO₃	F(000) = 560
M_r = 271.24	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2218 reflections
a = 7.7698 (16) Å	θ = 3.2–27.5°
b = 17.072 (3) Å	µ = 0.11 mm⁻¹
c = 9.759 (2) Å	T = 293 K
β = 96.72 (3)°	Bar, colourless
V = 1285.6 (5) Å³	0.3 × 0.3 × 0.2 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
φ and ω scans	h = −9→10
12293 measured reflections	k = −22→22
2921 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0695P)² + 0.2079P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₀FNO₃	V = 1285.6 (5) Å³
M_r = 271.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7698 (16) Å	µ = 0.11 mm⁻¹
b = 17.072 (3) Å	T = 293 K
c = 9.759 (2) Å	0.3 × 0.3 × 0.2 mm
β = 96.72 (3)°

Data collection top

Bruker SMART CCD diffractometer	2218 reflections with I > 2σ(I)
12293 measured reflections	R_int = 0.021
2921 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.13	Δρ_max = 0.24 e Å⁻³
2921 reflections	Δρ_min = −0.19 e Å⁻³
181 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
O3	0.08601 (15)	0.10025 (8)	0.43283 (13)	0.0659 (4)
C7	0.22626 (19)	0.11601 (9)	0.49650 (15)	0.0449 (3)
C9	0.18075 (19)	0.04525 (9)	0.70546 (15)	0.0469 (3)
H9A	0.0871	0.0226	0.6517	0.056*
C6	0.36095 (18)	0.15551 (8)	0.42269 (14)	0.0418 (3)
C8	0.27359 (19)	0.09685 (9)	0.64309 (15)	0.0472 (4)
H8A	0.3689	0.1209	0.6924	0.057*
C15	0.1386 (2)	−0.05036 (9)	0.88492 (16)	0.0495 (4)
H15A	0.0725	−0.0794	0.8173	0.059*
F1	0.27941 (18)	−0.06060 (9)	1.24775 (11)	0.0933 (4)
N1	0.13799 (19)	0.23833 (8)	0.29207 (17)	0.0589 (4)
C10	0.21056 (19)	0.02052 (9)	0.84967 (15)	0.0449 (3)
C11	0.3057 (2)	0.06445 (10)	0.95326 (16)	0.0522 (4)
H11A	0.3536	0.1122	0.9317	0.063*
C1	0.31757 (19)	0.20928 (9)	0.31805 (16)	0.0471 (4)
C5	0.5339 (2)	0.13342 (10)	0.44662 (16)	0.0521 (4)
H5A	0.5685	0.0977	0.5165	0.063*
C14	0.1637 (2)	−0.07817 (11)	1.01808 (18)	0.0569 (4)
H14A	0.1179	−0.1261	1.0408	0.068*
C12	0.3287 (2)	0.03713 (12)	1.08766 (17)	0.0595 (5)
H12A	0.3911	0.0661	1.1574	0.071*
C13	0.2572 (2)	−0.03371 (12)	1.11546 (16)	0.0593 (5)
C4	0.6559 (2)	0.16380 (12)	0.36778 (19)	0.0634 (5)
H4A	0.7714	0.1487	0.3857	0.076*
O2	0.07277 (18)	0.26603 (9)	0.38907 (18)	0.0830 (5)
C2	0.4367 (2)	0.23925 (11)	0.2374 (2)	0.0643 (5)
H2A	0.4026	0.2745	0.1667	0.077*
C3	0.6067 (3)	0.21593 (13)	0.2637 (2)	0.0702 (5)
H3A	0.6888	0.2356	0.2106	0.084*
O1	0.0655 (2)	0.23414 (11)	0.17437 (17)	0.0930 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0545 (7)	0.0779 (9)	0.0612 (7)	−0.0237 (6)	−0.0098 (5)	0.0163 (6)
C7	0.0435 (8)	0.0443 (8)	0.0459 (8)	−0.0029 (6)	0.0003 (6)	0.0010 (6)
C9	0.0446 (8)	0.0472 (8)	0.0477 (8)	−0.0016 (6)	0.0013 (6)	−0.0025 (6)
C6	0.0411 (7)	0.0437 (7)	0.0396 (7)	−0.0021 (6)	0.0009 (5)	−0.0065 (6)
C8	0.0424 (7)	0.0526 (9)	0.0455 (8)	−0.0057 (6)	0.0006 (6)	−0.0017 (6)
C15	0.0508 (8)	0.0491 (8)	0.0488 (8)	0.0039 (6)	0.0063 (7)	0.0005 (6)
F1	0.1009 (9)	0.1298 (11)	0.0478 (6)	0.0207 (8)	0.0028 (6)	0.0285 (6)
N1	0.0533 (8)	0.0473 (8)	0.0755 (10)	0.0011 (6)	0.0049 (7)	0.0163 (7)
C10	0.0432 (7)	0.0503 (8)	0.0417 (7)	0.0059 (6)	0.0076 (6)	−0.0004 (6)
C11	0.0486 (8)	0.0571 (9)	0.0515 (8)	−0.0001 (7)	0.0084 (7)	−0.0037 (7)
C1	0.0458 (8)	0.0396 (7)	0.0560 (9)	−0.0011 (6)	0.0070 (6)	0.0006 (6)
C5	0.0474 (8)	0.0621 (10)	0.0456 (8)	0.0040 (7)	0.0002 (6)	−0.0042 (7)
C14	0.0590 (9)	0.0554 (9)	0.0577 (9)	0.0109 (7)	0.0126 (8)	0.0124 (7)
C12	0.0538 (9)	0.0791 (12)	0.0448 (8)	0.0068 (8)	0.0020 (7)	−0.0115 (8)
C13	0.0555 (9)	0.0819 (12)	0.0411 (8)	0.0204 (9)	0.0075 (7)	0.0121 (8)
C4	0.0413 (8)	0.0821 (13)	0.0678 (11)	0.0007 (8)	0.0105 (8)	−0.0142 (9)
O2	0.0623 (8)	0.0779 (10)	0.1116 (12)	0.0149 (7)	0.0225 (8)	−0.0109 (8)
C2	0.0669 (11)	0.0554 (10)	0.0734 (12)	−0.0025 (8)	0.0199 (9)	0.0147 (8)
C3	0.0601 (11)	0.0744 (12)	0.0809 (13)	−0.0075 (9)	0.0287 (10)	0.0056 (10)
O1	0.0797 (10)	0.1129 (13)	0.0809 (10)	0.0104 (9)	−0.0132 (8)	0.0361 (9)

Geometric parameters (Å, º) top

O3—C7	1.2195 (18)	C10—C11	1.399 (2)
C7—C8	1.472 (2)	C11—C12	1.384 (2)
C7—C6	1.498 (2)	C11—H11A	0.9300
C9—C8	1.330 (2)	C1—C2	1.382 (2)
C9—C10	1.462 (2)	C5—C4	1.390 (2)
C9—H9A	0.9300	C5—H5A	0.9300
C6—C1	1.385 (2)	C14—C13	1.359 (3)
C6—C5	1.389 (2)	C14—H14A	0.9300
C8—H8A	0.9300	C12—C13	1.371 (3)
C15—C14	1.376 (2)	C12—H12A	0.9300
C15—C10	1.393 (2)	C4—C3	1.371 (3)
C15—H15A	0.9300	C4—H4A	0.9300
F1—C13	1.3619 (18)	C2—C3	1.375 (3)
N1—O2	1.220 (2)	C2—H2A	0.9300
N1—O1	1.221 (2)	C3—H3A	0.9300
N1—C1	1.475 (2)

O3—C7—C8	123.58 (14)	C2—C1—C6	122.96 (15)
O3—C7—C6	119.14 (13)	C2—C1—N1	117.45 (15)
C8—C7—C6	117.27 (12)	C6—C1—N1	119.56 (13)
C8—C9—C10	126.77 (14)	C6—C5—C4	121.00 (16)
C8—C9—H9A	116.6	C6—C5—H5A	119.5
C10—C9—H9A	116.6	C4—C5—H5A	119.5
C1—C6—C5	116.81 (14)	C13—C14—C15	118.23 (17)
C1—C6—C7	121.96 (13)	C13—C14—H14A	120.9
C5—C6—C7	120.89 (14)	C15—C14—H14A	120.9
C9—C8—C7	120.32 (14)	C13—C12—C11	118.32 (16)
C9—C8—H8A	119.8	C13—C12—H12A	120.8
C7—C8—H8A	119.8	C11—C12—H12A	120.8
C14—C15—C10	121.09 (16)	C14—C13—F1	118.22 (18)
C14—C15—H15A	119.5	C14—C13—C12	123.39 (15)
C10—C15—H15A	119.5	F1—C13—C12	118.40 (17)
O2—N1—O1	124.40 (16)	C3—C4—C5	120.24 (16)
O2—N1—C1	117.87 (15)	C3—C4—H4A	119.9
O1—N1—C1	117.71 (16)	C5—C4—H4A	119.9
C15—C10—C11	118.74 (14)	C3—C2—C1	118.66 (17)
C15—C10—C9	117.76 (14)	C3—C2—H2A	120.7
C11—C10—C9	123.49 (15)	C1—C2—H2A	120.7
C12—C11—C10	120.21 (16)	C4—C3—C2	120.31 (16)
C12—C11—H11A	119.9	C4—C3—H3A	119.8
C10—C11—H11A	119.9	C2—C3—H3A	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3ⁱ	0.93	2.57	3.500 (2)	177
C5—H5A···F1ⁱⁱ	0.93	2.54	3.396 (2)	153
C9—H9A···O3	0.93	2.51	2.836 (2)	101
C9—H9A···O3ⁱⁱⁱ	0.93	2.57	3.411 (2)	150

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FNO₃
M_r	271.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.7698 (16), 17.072 (3), 9.759 (2)
β (°)	96.72 (3)
V (Å³)	1285.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12293, 2921, 2218
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.141, 1.13
No. of reflections	2921
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
C4—H4A···O3ⁱ	0.93	2.57	3.500 (2)	177.3
C5—H5A···F1ⁱⁱ	0.93	2.54	3.396 (2)	153.0
C9—H9A···O3ⁱⁱⁱ	0.93	2.57	3.411 (2)	149.9

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

Acknowledgements

The authors would like to thank the National Natural Science Foundation of Shandong Province (2009ZRA07002).

References

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