(E)-3-(4-Fluoro-phen-yl)-1-(2-nitro-phen-yl)prop-2-en-1-one.

The title compound, C(15)H(10)F(N)O(3), was prepared from 2-nitro-acetphenone and 4-fluoro-benzaldehyde 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 inter-molecular 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 = 271.24

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.141

S = 1.13

2921 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001809X/lh5041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001809X/lh5041Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H10FNO3	F(000) = 560
Mr = 271.24	Dx = 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

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

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(Fo2) + (0.0695P)2 + 0.2079P] where P = (Fo2 + 2Fc2)/3
2921 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 e Å−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	Uiso*/Ueq
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)

	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)

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

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

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) ; (ii) ; (iii) .