organic compounds
3-(4-Methoxyphenyl)-1-(2-nitrophenyl)prop-2-en-1-one
aMicroscale Science Institute , Weifang University, Weifang 261061, People's Republic of China, and bthe Seventh Middle School of Wei Fang, Weifang 261041, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com
The title compound, C16H13NO4, was prepared from 2-nitrylhypnone [systematic name: 1-(2-nitrophenyl)ethanone] and 4-methoxybenzophenone by a Claisen–Schmidt condensation. The dihedral angle formed by the two benzene rings is 80.73 (2). The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds.
Related literature
For the biological activity of et al. (1994); De Vincenzo et al. (2000); Dimmock et al. (1998); Hsieh et al. (1998). For a related structure, see: Fun et al. (2008).
see: AntoExperimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 1997); cell 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
10.1107/S1600536809048120/fl2279sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809048120/fl2279Isup2.hkl
The title compound(I) was prepared by the process as following: A mixture of the 2-nitrylhypnone (0.02 mol), 4-methoxybenzophenone(0.02 mol) and 10%NaOH(10 ml) was stirred in ethanol(30 ml) for 3 h to afford the title compound(yield78%).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 of0.93–0.96 Å, and with Uiso(H) = 1.2Ueq of the parent atoms.
Data collection: SMART (Bruker, 1997); cell
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).C16H13NO4 | F(000) = 592 |
Mr = 283.27 | Dx = 1.380 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2667 reflections |
a = 11.594 (2) Å | θ = 3.1–27.5° |
b = 7.7736 (16) Å | µ = 0.10 mm−1 |
c = 15.174 (3) Å | T = 293 K |
β = 94.59 (3)° | Bar, yellow |
V = 1363.1 (5) Å3 | 0.21 × 0.18 × 0.10 mm |
Z = 4 |
Bruker sMART CCD area-detector diffractometer | 2667 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
phi and ω scans | h = −15→15 |
12773 measured reflections | k = −10→8 |
3107 independent reflections | l = −19→19 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3 |
3107 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C16H13NO4 | V = 1363.1 (5) Å3 |
Mr = 283.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.594 (2) Å | µ = 0.10 mm−1 |
b = 7.7736 (16) Å | T = 293 K |
c = 15.174 (3) Å | 0.21 × 0.18 × 0.10 mm |
β = 94.59 (3)° |
Bruker sMART CCD area-detector diffractometer | 2667 reflections with I > 2σ(I) |
12773 measured reflections | Rint = 0.018 |
3107 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.19 e Å−3 |
3107 reflections | Δρmin = −0.22 e Å−3 |
190 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 | ||
C8 | 0.72395 (9) | 0.18277 (14) | 0.22201 (7) | 0.0385 (2) | |
H8A | 0.7810 | 0.2655 | 0.2340 | 0.046* | |
O4 | 0.82958 (9) | 0.02414 (13) | 0.02294 (6) | 0.0603 (3) | |
C5 | 0.63411 (9) | 0.17369 (13) | 0.28408 (7) | 0.0371 (2) | |
N1 | 1.07316 (9) | 0.10395 (13) | 0.16402 (6) | 0.0447 (2) | |
C2 | 0.46388 (9) | 0.17332 (14) | 0.40548 (8) | 0.0402 (3) | |
C7 | 0.44279 (10) | 0.09466 (16) | 0.32265 (8) | 0.0482 (3) | |
H7A | 0.3714 | 0.0436 | 0.3073 | 0.058* | |
O3 | 1.01265 (9) | −0.02297 (12) | 0.16921 (7) | 0.0611 (3) | |
C16 | 0.85299 (10) | 0.42736 (15) | 0.08146 (8) | 0.0442 (3) | |
H16A | 0.7755 | 0.4334 | 0.0604 | 0.053* | |
C11 | 0.90152 (9) | 0.26829 (14) | 0.10358 (7) | 0.0359 (2) | |
C12 | 1.01784 (9) | 0.26616 (13) | 0.13472 (7) | 0.0362 (2) | |
C6 | 0.52710 (10) | 0.09263 (15) | 0.26394 (8) | 0.0445 (3) | |
H6A | 0.5130 | 0.0366 | 0.2100 | 0.053* | |
C13 | 1.08378 (10) | 0.41407 (16) | 0.14300 (8) | 0.0454 (3) | |
H13A | 1.1615 | 0.4087 | 0.1636 | 0.054* | |
C9 | 0.73401 (10) | 0.08635 (15) | 0.15007 (8) | 0.0435 (3) | |
H9A | 0.6811 | −0.0023 | 0.1384 | 0.052* | |
C14 | 1.03253 (12) | 0.57038 (15) | 0.12026 (9) | 0.0514 (3) | |
H14A | 1.0760 | 0.6710 | 0.1254 | 0.062* | |
C4 | 0.65192 (9) | 0.25538 (14) | 0.36590 (8) | 0.0414 (3) | |
H4A | 0.7213 | 0.3129 | 0.3799 | 0.050* | |
O2 | 1.17769 (9) | 0.10328 (15) | 0.18354 (8) | 0.0719 (3) | |
C10 | 0.82364 (10) | 0.11242 (15) | 0.08857 (7) | 0.0409 (3) | |
C15 | 0.91755 (12) | 0.57743 (15) | 0.09011 (9) | 0.0493 (3) | |
H15A | 0.8831 | 0.6828 | 0.0755 | 0.059* | |
C3 | 0.56915 (10) | 0.25320 (14) | 0.42687 (8) | 0.0410 (3) | |
H3A | 0.5842 | 0.3051 | 0.4818 | 0.049* | |
O1 | 0.37527 (8) | 0.16582 (14) | 0.45895 (6) | 0.0582 (3) | |
C1 | 0.39013 (13) | 0.24330 (19) | 0.54405 (9) | 0.0596 (4) | |
H1A | 0.3210 | 0.2283 | 0.5740 | 0.089* | |
H1B | 0.4054 | 0.3639 | 0.5378 | 0.089* | |
H1C | 0.4540 | 0.1900 | 0.5778 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C8 | 0.0357 (5) | 0.0373 (5) | 0.0419 (5) | −0.0036 (4) | −0.0006 (4) | 0.0031 (4) |
O4 | 0.0715 (6) | 0.0603 (6) | 0.0498 (5) | −0.0125 (5) | 0.0103 (4) | −0.0185 (4) |
C5 | 0.0369 (5) | 0.0338 (5) | 0.0400 (5) | −0.0028 (4) | 0.0002 (4) | 0.0032 (4) |
N1 | 0.0496 (5) | 0.0450 (5) | 0.0397 (5) | 0.0120 (4) | 0.0042 (4) | −0.0005 (4) |
C2 | 0.0387 (5) | 0.0357 (5) | 0.0467 (6) | −0.0029 (4) | 0.0060 (4) | 0.0029 (4) |
C7 | 0.0404 (6) | 0.0522 (7) | 0.0516 (7) | −0.0158 (5) | 0.0010 (5) | −0.0042 (5) |
O3 | 0.0728 (6) | 0.0398 (5) | 0.0711 (6) | 0.0075 (4) | 0.0090 (5) | 0.0099 (4) |
C16 | 0.0426 (6) | 0.0422 (6) | 0.0481 (6) | 0.0065 (4) | 0.0056 (5) | 0.0045 (5) |
C11 | 0.0386 (5) | 0.0361 (5) | 0.0338 (5) | 0.0004 (4) | 0.0068 (4) | −0.0003 (4) |
C12 | 0.0396 (5) | 0.0365 (5) | 0.0330 (5) | 0.0047 (4) | 0.0061 (4) | −0.0024 (4) |
C6 | 0.0438 (6) | 0.0472 (6) | 0.0419 (6) | −0.0112 (5) | −0.0004 (5) | −0.0041 (5) |
C13 | 0.0394 (5) | 0.0485 (7) | 0.0487 (6) | −0.0032 (5) | 0.0060 (5) | −0.0088 (5) |
C9 | 0.0432 (6) | 0.0406 (6) | 0.0466 (6) | −0.0093 (4) | 0.0018 (5) | −0.0011 (5) |
C14 | 0.0590 (7) | 0.0378 (6) | 0.0590 (7) | −0.0104 (5) | 0.0145 (6) | −0.0077 (5) |
C4 | 0.0349 (5) | 0.0418 (6) | 0.0467 (6) | −0.0067 (4) | −0.0012 (4) | −0.0029 (5) |
O2 | 0.0501 (6) | 0.0756 (7) | 0.0877 (8) | 0.0208 (5) | −0.0089 (5) | 0.0045 (6) |
C10 | 0.0440 (6) | 0.0387 (6) | 0.0396 (5) | −0.0008 (4) | 0.0007 (4) | −0.0014 (4) |
C15 | 0.0618 (7) | 0.0337 (6) | 0.0537 (7) | 0.0077 (5) | 0.0134 (6) | 0.0041 (5) |
C3 | 0.0406 (6) | 0.0400 (6) | 0.0417 (5) | −0.0026 (4) | −0.0006 (4) | −0.0044 (4) |
O1 | 0.0492 (5) | 0.0682 (6) | 0.0593 (5) | −0.0160 (4) | 0.0177 (4) | −0.0100 (5) |
C1 | 0.0642 (8) | 0.0620 (8) | 0.0548 (7) | 0.0018 (6) | 0.0188 (6) | −0.0020 (6) |
C8—C9 | 1.3369 (17) | C11—C10 | 1.5174 (15) |
C8—C5 | 1.4609 (16) | C12—C13 | 1.3809 (16) |
C8—H8A | 0.9300 | C6—H6A | 0.9300 |
O4—C10 | 1.2159 (15) | C13—C14 | 1.3841 (18) |
C5—C4 | 1.3951 (16) | C13—H13A | 0.9300 |
C5—C6 | 1.4031 (15) | C9—C10 | 1.4653 (17) |
N1—O3 | 1.2168 (14) | C9—H9A | 0.9300 |
N1—O2 | 1.2242 (15) | C14—C15 | 1.3753 (19) |
N1—C12 | 1.4674 (14) | C14—H14A | 0.9300 |
C2—O1 | 1.3604 (14) | C4—C3 | 1.3854 (17) |
C2—C3 | 1.3846 (16) | C4—H4A | 0.9300 |
C2—C7 | 1.4015 (17) | C15—H15A | 0.9300 |
C7—C6 | 1.3743 (18) | C3—H3A | 0.9300 |
C7—H7A | 0.9300 | O1—C1 | 1.4227 (17) |
C16—C15 | 1.3866 (18) | C1—H1A | 0.9600 |
C16—C11 | 1.3885 (15) | C1—H1B | 0.9600 |
C16—H16A | 0.9300 | C1—H1C | 0.9600 |
C11—C12 | 1.3929 (15) | ||
C9—C8—C5 | 127.78 (10) | C12—C13—H13A | 120.5 |
C9—C8—H8A | 116.1 | C14—C13—H13A | 120.5 |
C5—C8—H8A | 116.1 | C8—C9—C10 | 123.72 (10) |
C4—C5—C6 | 117.62 (10) | C8—C9—H9A | 118.1 |
C4—C5—C8 | 119.30 (9) | C10—C9—H9A | 118.1 |
C6—C5—C8 | 123.02 (10) | C15—C14—C13 | 120.22 (11) |
O3—N1—O2 | 123.06 (11) | C15—C14—H14A | 119.9 |
O3—N1—C12 | 118.43 (10) | C13—C14—H14A | 119.9 |
O2—N1—C12 | 118.50 (11) | C3—C4—C5 | 121.84 (10) |
O1—C2—C3 | 124.96 (11) | C3—C4—H4A | 119.1 |
O1—C2—C7 | 115.49 (10) | C5—C4—H4A | 119.1 |
C3—C2—C7 | 119.55 (11) | O4—C10—C9 | 122.22 (11) |
C6—C7—C2 | 120.28 (10) | O4—C10—C11 | 120.10 (11) |
C6—C7—H7A | 119.9 | C9—C10—C11 | 117.30 (9) |
C2—C7—H7A | 119.9 | C14—C15—C16 | 119.96 (11) |
C15—C16—C11 | 121.41 (11) | C14—C15—H15A | 120.0 |
C15—C16—H16A | 119.3 | C16—C15—H15A | 120.0 |
C11—C16—H16A | 119.3 | C2—C3—C4 | 119.58 (10) |
C16—C11—C12 | 117.07 (10) | C2—C3—H3A | 120.2 |
C16—C11—C10 | 116.75 (10) | C4—C3—H3A | 120.2 |
C12—C11—C10 | 126.14 (9) | C2—O1—C1 | 118.75 (10) |
C13—C12—C11 | 122.33 (10) | O1—C1—H1A | 109.5 |
C13—C12—N1 | 117.55 (10) | O1—C1—H1B | 109.5 |
C11—C12—N1 | 120.05 (10) | H1A—C1—H1B | 109.5 |
C7—C6—C5 | 121.06 (11) | O1—C1—H1C | 109.5 |
C7—C6—H6A | 119.5 | H1A—C1—H1C | 109.5 |
C5—C6—H6A | 119.5 | H1B—C1—H1C | 109.5 |
C12—C13—C14 | 119.00 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.93 | 2.51 | 3.249 (1) | 136 |
C14—H14A···O3ii | 0.93 | 2.59 | 3.259 (2) | 129 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13NO4 |
Mr | 283.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.594 (2), 7.7736 (16), 15.174 (3) |
β (°) | 94.59 (3) |
V (Å3) | 1363.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.21 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Bruker sMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12773, 3107, 2667 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.124, 1.08 |
No. of reflections | 3107 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.22 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.93 | 2.51 | 3.249 (1) | 136 |
C14—H14A···O3ii | 0.93 | 2.59 | 3.259 (2) | 129 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y+1, z. |
Acknowledgements
The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and the Yuandu Scholar Fund of Weifang City for support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998)and antioxidant (Anto et al.,1994). Of particular interest, the effectiveness of chalcones againest 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.
Scheme I
The molecule (I) (Fig. 1) is made up of two essentially planar segments. The atoms O1, C1,C2, C3, C4, C5, C6 and C7 make up one segment (largest deviation being 0.018Å for C6) with the nitro phenyl group being the second planar segment (largest deviation 0.0177Å for N1).The dihedral angel formed by the two planes is 81.07 (2)°. All of the bond lengths and bond angles are in normal ranges and comparable to those found in a related structure (Fun et al., 2008). In the crystal structure, the molecules are stacked along the b axis and linked via C—H···O interactions (Fig. 2).