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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2510.
Published online 2009 September 26. doi:  10.1107/S1600536809037556
PMCID: PMC2970181

(E)-1-(4-Nitro­phen­yl)-3-phenyl­prop-2-en-1-one

Abstract

In the title compound, C15H11NO3, the configuration of the keto group with respect to the olefinic double bond is s–cis. The two benzene rings form a dihedral angle of 5.00 (5)°. The mol­ecules are linked into a two-dimensional network parallel to (An external file that holds a picture, illustration, etc.
Object name is e-65-o2510-efi1.jpg04) by C—H(...)O hydrogen bonds.

Related literature

For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 [triangle]). For the synthesis, see: Cocconcelli et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2510-scheme1.jpg

Experimental

Crystal data

  • C15H11NO3
  • M r = 253.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2510-efi2.jpg
  • a = 6.2139 (10) Å
  • b = 13.159 (2) Å
  • c = 14.450 (3) Å
  • β = 92.106 (3)°
  • V = 1180.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 93 K
  • 0.50 × 0.18 × 0.18 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: none
  • 9403 measured reflections
  • 2687 independent reflections
  • 2264 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.097
  • S = 1.00
  • 2687 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037556/ci2913sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037556/ci2913Isup2.hkl

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

Acknowledgments

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

supplementary crystallographic information

Comment

Chalcone derivatives are a class of important compounds that possess antiprotzoal, antihelmintic, amoebicidal, anti-ulcer, antiviral, insecticidal, antibacterial, anticancer, cytotoxic and immunosuppressive activities (Dimmock et al., 1999). The crystal structures of some chalcone derivatives have been reported. We report here the crystal structure of the title compound.

Bond lengths and angles in the title molecule are normal. The configuration of the keto group with respect to the olefinic double bond is typically s-cis, with a O1—C9—C8—C7 torsion angle of 0.5 (2)° (Fig. 1). The N1/O2/O3 and C10-C15 planes form a dihedral angle of 10.80 (11)°. The two benzene rings (C10-C15 and C1-C6) form a dihedral angle of 5.00 (5)°. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1). The molecules are linked into a two-dimensional network parallel to the (1 0 4) by the above hydrogen bonds.

Experimental

The title compound was synthesized according to the method reported in the literature (Cocconcelli et al., 2008). Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a acetone solution.

Refinement

All H atoms were placed in calculated positions, with C-H = 0.95 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

Crystal data

C15H11NO3F(000) = 528
Mr = 253.25Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3448 reflections
a = 6.2139 (10) Åθ = 3.1–27.5°
b = 13.159 (2) ŵ = 0.10 mm1
c = 14.450 (3) ÅT = 93 K
β = 92.106 (3)°Needle, yellow
V = 1180.8 (3) Å30.50 × 0.18 × 0.18 mm
Z = 4

Data collection

Rigaku SPIDER diffractometer2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 27.5°, θmin = 3.1°
ω scansh = −8→7
9403 measured reflectionsk = −17→17
2687 independent reflectionsl = −18→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0516P)2 + 0.336P] where P = (Fo2 + 2Fc2)/3
2687 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

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.

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

xyzUiso*/Ueq
O10.19885 (14)0.39882 (7)0.06264 (7)0.0243 (2)
O20.89968 (15)0.02961 (7)0.20944 (7)0.0266 (2)
O31.11753 (14)0.14090 (7)0.27163 (7)0.0272 (2)
N10.94974 (16)0.11770 (8)0.22851 (7)0.0185 (2)
C10.11212 (19)0.77346 (9)0.04561 (8)0.0179 (3)
H1−0.01640.73950.02580.021*
C20.1184 (2)0.87899 (9)0.04625 (9)0.0209 (3)
H2−0.00590.91690.02770.025*
C30.3061 (2)0.92892 (9)0.07402 (9)0.0221 (3)
H30.31041.00110.07410.027*
C40.4885 (2)0.87379 (9)0.10183 (8)0.0205 (3)
H40.61700.90830.12060.025*
C50.48224 (19)0.76832 (9)0.10203 (8)0.0180 (3)
H50.60660.73090.12140.022*
C60.29377 (19)0.71675 (9)0.07389 (8)0.0158 (3)
C70.27514 (19)0.60597 (9)0.07315 (8)0.0163 (2)
H70.14690.57890.04510.020*
C80.41785 (19)0.53830 (9)0.10745 (8)0.0169 (3)
H80.54960.56040.13620.020*
C90.36764 (19)0.42863 (9)0.10009 (8)0.0167 (3)
C100.52508 (19)0.35096 (9)0.13838 (8)0.0155 (2)
C110.72971 (19)0.37564 (9)0.17453 (8)0.0173 (3)
H110.77330.44480.17800.021*
C120.87037 (19)0.29959 (9)0.20556 (8)0.0172 (3)
H121.00950.31580.23080.021*
C130.80212 (19)0.19972 (9)0.19868 (8)0.0158 (3)
C140.59903 (19)0.17265 (9)0.16446 (8)0.0174 (3)
H140.55580.10340.16180.021*
C150.46102 (19)0.24900 (9)0.13438 (8)0.0172 (3)
H150.32090.23220.11070.021*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0198 (5)0.0168 (4)0.0355 (5)−0.0023 (4)−0.0093 (4)0.0018 (4)
O20.0289 (5)0.0153 (4)0.0349 (5)0.0044 (4)−0.0061 (4)−0.0033 (4)
O30.0188 (5)0.0252 (5)0.0367 (6)0.0010 (4)−0.0095 (4)0.0031 (4)
N10.0180 (5)0.0183 (5)0.0190 (5)0.0018 (4)0.0005 (4)0.0008 (4)
C10.0174 (6)0.0176 (6)0.0184 (6)−0.0015 (5)−0.0016 (5)0.0006 (5)
C20.0212 (6)0.0174 (6)0.0238 (6)0.0029 (5)−0.0032 (5)0.0021 (5)
C30.0278 (7)0.0132 (5)0.0250 (6)−0.0008 (5)−0.0022 (5)−0.0002 (5)
C40.0206 (6)0.0186 (6)0.0221 (6)−0.0039 (5)−0.0017 (5)−0.0014 (5)
C50.0168 (6)0.0190 (6)0.0181 (6)0.0007 (5)−0.0004 (5)0.0013 (5)
C60.0180 (6)0.0158 (6)0.0136 (5)0.0005 (4)0.0013 (4)0.0001 (4)
C70.0164 (6)0.0166 (6)0.0160 (6)−0.0012 (4)0.0004 (4)−0.0004 (4)
C80.0157 (6)0.0161 (6)0.0187 (6)−0.0021 (4)−0.0016 (5)−0.0009 (4)
C90.0169 (6)0.0161 (6)0.0170 (6)−0.0007 (5)0.0003 (5)0.0006 (4)
C100.0168 (6)0.0148 (5)0.0147 (6)0.0006 (4)0.0002 (4)−0.0001 (4)
C110.0186 (6)0.0142 (5)0.0189 (6)−0.0019 (5)−0.0004 (5)−0.0004 (4)
C120.0151 (6)0.0182 (6)0.0181 (6)−0.0015 (4)−0.0015 (5)−0.0002 (4)
C130.0172 (6)0.0160 (6)0.0142 (5)0.0033 (4)0.0004 (4)0.0006 (4)
C140.0211 (6)0.0136 (5)0.0176 (6)−0.0007 (5)−0.0010 (5)−0.0008 (4)
C150.0160 (6)0.0170 (6)0.0183 (6)−0.0018 (4)−0.0024 (5)0.0001 (4)

Geometric parameters (Å, °)

O1—C91.2268 (15)C7—C81.3389 (17)
O2—N11.2289 (14)C7—H70.95
O3—N11.2331 (14)C8—C91.4795 (16)
N1—C131.4708 (15)C8—H80.95
C1—C21.3893 (17)C9—C101.5060 (16)
C1—C61.4014 (17)C10—C111.3951 (17)
C1—H10.95C10—C151.4000 (16)
C2—C31.3851 (18)C11—C121.3920 (17)
C2—H20.95C11—H110.95
C3—C41.3923 (18)C12—C131.3835 (17)
C3—H30.95C12—H120.95
C4—C51.3885 (17)C13—C141.3850 (17)
C4—H40.95C14—C151.3808 (16)
C5—C61.4009 (17)C14—H140.95
C5—H50.95C15—H150.95
C6—C71.4624 (16)
O2—N1—O3123.31 (10)C7—C8—C9119.15 (11)
O2—N1—C13118.46 (10)C7—C8—H8120.4
O3—N1—C13118.23 (10)C9—C8—H8120.4
C2—C1—C6120.54 (11)O1—C9—C8121.21 (11)
C2—C1—H1119.7O1—C9—C10118.58 (11)
C6—C1—H1119.7C8—C9—C10120.21 (10)
C3—C2—C1119.95 (11)C11—C10—C15119.50 (11)
C3—C2—H2120.0C11—C10—C9123.39 (11)
C1—C2—H2120.0C15—C10—C9117.09 (11)
C2—C3—C4120.28 (11)C12—C11—C10120.40 (11)
C2—C3—H3119.9C12—C11—H11119.8
C4—C3—H3119.9C10—C11—H11119.8
C5—C4—C3119.93 (11)C13—C12—C11118.21 (11)
C5—C4—H4120.0C13—C12—H12120.9
C3—C4—H4120.0C11—C12—H12120.9
C4—C5—C6120.44 (11)C12—C13—C14122.88 (11)
C4—C5—H5119.8C12—C13—N1119.33 (11)
C6—C5—H5119.8C14—C13—N1117.79 (10)
C5—C6—C1118.85 (11)C15—C14—C13118.19 (11)
C5—C6—C7123.37 (11)C15—C14—H14120.9
C1—C6—C7117.77 (11)C13—C14—H14120.9
C8—C7—C6127.53 (11)C14—C15—C10120.80 (11)
C8—C7—H7116.2C14—C15—H15119.6
C6—C7—H7116.2C10—C15—H15119.6
C6—C1—C2—C30.74 (19)C8—C9—C10—C15175.96 (10)
C1—C2—C3—C4−0.36 (19)C15—C10—C11—C120.67 (18)
C2—C3—C4—C5−0.20 (19)C9—C10—C11—C12−177.52 (11)
C3—C4—C5—C60.38 (18)C10—C11—C12—C130.57 (18)
C4—C5—C6—C10.00 (18)C11—C12—C13—C14−1.58 (18)
C4—C5—C6—C7−179.43 (11)C11—C12—C13—N1178.29 (10)
C2—C1—C6—C5−0.56 (18)O2—N1—C13—C12−169.34 (11)
C2—C1—C6—C7178.91 (11)O3—N1—C13—C1210.81 (16)
C5—C6—C7—C88.14 (19)O2—N1—C13—C1410.54 (16)
C1—C6—C7—C8−171.29 (12)O3—N1—C13—C14−169.31 (11)
C6—C7—C8—C9179.69 (11)C12—C13—C14—C151.28 (18)
C7—C8—C9—O10.54 (18)N1—C13—C14—C15−178.59 (10)
C7—C8—C9—C10−179.81 (11)C13—C14—C15—C100.04 (17)
O1—C9—C10—C11173.86 (12)C11—C10—C15—C14−0.99 (18)
C8—C9—C10—C11−5.80 (17)C9—C10—C15—C14177.32 (11)
O1—C9—C10—C15−4.38 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.473.3314 (15)150
C5—H5···O3ii0.952.563.4635 (16)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2913).

References

  • Cocconcelli, G., Diodato, E., Caricasole, A., Gaviraghi, G., Genesio, E., Ghiron, C., Magnoni, L., Pecchioli, E., Plazzi, P. V. & Terstappen, G. C. (2008). Bioorg. Med. Chem.16, 2043–2052. [PubMed]
  • Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem.6, 1125–1149. [PubMed]
  • Rigaku (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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