Acta Cryst. (2010). E66, o1414 [ doi:10.1107/S160053681001809X ]
The title compound, C15H10FNO3, 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-HF hydrogen bonds.
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.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93 Å, and with Uiso(H) = 1.2Ueq of the parent atoms.
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).
![[Figure 1]](./lh5041fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| 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 |
| C15H10FNO3 | V = 1285.6 (5) Å3 |
| Mr = 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)° |
| Bruker SMART CCD diffractometer | 2218 reflections with I > 2σ(I) |
| 12293 measured reflections | Rint = 0.021 |
| 2921 independent reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.141 | Δρmax = 0.24 e Å−3 |
| S = 1.13 | Δρmin = −0.19 e Å−3 |
| 2921 reflections | Absolute structure: ? |
| 181 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 |
| Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+1. |
| 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. |
The authors would like to thank the National Natural Science Foundation of Shandong Province (2009ZRA07002) .
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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.