PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3117.
Published online 2009 November 18. doi:  10.1107/S1600536809048120
PMCID: PMC2971945

3-(4-Methoxy­phen­yl)-1-(2-nitrophen­yl)prop-2-en-1-one

Abstract

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 chalcones, see: Anto et al. (1994 [triangle]); De Vincenzo et al. (2000 [triangle]); Dimmock et al. (1998 [triangle]); Hsieh et al. (1998 [triangle]). For a related structure, see: Fun et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3117-scheme1.jpg

Experimental

Crystal data

  • C16H13NO4
  • M r = 283.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3117-efi1.jpg
  • a = 11.594 (2) Å
  • b = 7.7736 (16) Å
  • c = 15.174 (3) Å
  • β = 94.59 (3)°
  • V = 1363.1 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.21 × 0.18 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 12773 measured reflections
  • 3107 independent reflections
  • 2667 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.124
  • S = 1.08
  • 3107 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048120/fl2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048120/fl2279Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title compound,viewed along a axis.

Crystal data

C16H13NO4F(000) = 592
Mr = 283.27Dx = 1.380 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2667 reflections
a = 11.594 (2) Åθ = 3.1–27.5°
b = 7.7736 (16) ŵ = 0.10 mm1
c = 15.174 (3) ÅT = 293 K
β = 94.59 (3)°Bar, yellow
V = 1363.1 (5) Å30.21 × 0.18 × 0.10 mm
Z = 4

Data collection

Bruker sMART CCD area-detector diffractometer2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 27.5°, θmin = 3.1°
phi and ω scansh = −15→15
12773 measured reflectionsk = −10→8
3107 independent reflectionsl = −19→19

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0747P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3
3107 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.22 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
C80.72395 (9)0.18277 (14)0.22201 (7)0.0385 (2)
H8A0.78100.26550.23400.046*
O40.82958 (9)0.02414 (13)0.02294 (6)0.0603 (3)
C50.63411 (9)0.17369 (13)0.28408 (7)0.0371 (2)
N11.07316 (9)0.10395 (13)0.16402 (6)0.0447 (2)
C20.46388 (9)0.17332 (14)0.40548 (8)0.0402 (3)
C70.44279 (10)0.09466 (16)0.32265 (8)0.0482 (3)
H7A0.37140.04360.30730.058*
O31.01265 (9)−0.02297 (12)0.16921 (7)0.0611 (3)
C160.85299 (10)0.42736 (15)0.08146 (8)0.0442 (3)
H16A0.77550.43340.06040.053*
C110.90152 (9)0.26829 (14)0.10358 (7)0.0359 (2)
C121.01784 (9)0.26616 (13)0.13472 (7)0.0362 (2)
C60.52710 (10)0.09263 (15)0.26394 (8)0.0445 (3)
H6A0.51300.03660.21000.053*
C131.08378 (10)0.41407 (16)0.14300 (8)0.0454 (3)
H13A1.16150.40870.16360.054*
C90.73401 (10)0.08635 (15)0.15007 (8)0.0435 (3)
H9A0.6811−0.00230.13840.052*
C141.03253 (12)0.57038 (15)0.12026 (9)0.0514 (3)
H14A1.07600.67100.12540.062*
C40.65192 (9)0.25538 (14)0.36590 (8)0.0414 (3)
H4A0.72130.31290.37990.050*
O21.17769 (9)0.10328 (15)0.18354 (8)0.0719 (3)
C100.82364 (10)0.11242 (15)0.08857 (7)0.0409 (3)
C150.91755 (12)0.57743 (15)0.09011 (9)0.0493 (3)
H15A0.88310.68280.07550.059*
C30.56915 (10)0.25320 (14)0.42687 (8)0.0410 (3)
H3A0.58420.30510.48180.049*
O10.37527 (8)0.16582 (14)0.45895 (6)0.0582 (3)
C10.39013 (13)0.24330 (19)0.54405 (9)0.0596 (4)
H1A0.32100.22830.57400.089*
H1B0.40540.36390.53780.089*
H1C0.45400.19000.57780.089*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C80.0357 (5)0.0373 (5)0.0419 (5)−0.0036 (4)−0.0006 (4)0.0031 (4)
O40.0715 (6)0.0603 (6)0.0498 (5)−0.0125 (5)0.0103 (4)−0.0185 (4)
C50.0369 (5)0.0338 (5)0.0400 (5)−0.0028 (4)0.0002 (4)0.0032 (4)
N10.0496 (5)0.0450 (5)0.0397 (5)0.0120 (4)0.0042 (4)−0.0005 (4)
C20.0387 (5)0.0357 (5)0.0467 (6)−0.0029 (4)0.0060 (4)0.0029 (4)
C70.0404 (6)0.0522 (7)0.0516 (7)−0.0158 (5)0.0010 (5)−0.0042 (5)
O30.0728 (6)0.0398 (5)0.0711 (6)0.0075 (4)0.0090 (5)0.0099 (4)
C160.0426 (6)0.0422 (6)0.0481 (6)0.0065 (4)0.0056 (5)0.0045 (5)
C110.0386 (5)0.0361 (5)0.0338 (5)0.0004 (4)0.0068 (4)−0.0003 (4)
C120.0396 (5)0.0365 (5)0.0330 (5)0.0047 (4)0.0061 (4)−0.0024 (4)
C60.0438 (6)0.0472 (6)0.0419 (6)−0.0112 (5)−0.0004 (5)−0.0041 (5)
C130.0394 (5)0.0485 (7)0.0487 (6)−0.0032 (5)0.0060 (5)−0.0088 (5)
C90.0432 (6)0.0406 (6)0.0466 (6)−0.0093 (4)0.0018 (5)−0.0011 (5)
C140.0590 (7)0.0378 (6)0.0590 (7)−0.0104 (5)0.0145 (6)−0.0077 (5)
C40.0349 (5)0.0418 (6)0.0467 (6)−0.0067 (4)−0.0012 (4)−0.0029 (5)
O20.0501 (6)0.0756 (7)0.0877 (8)0.0208 (5)−0.0089 (5)0.0045 (6)
C100.0440 (6)0.0387 (6)0.0396 (5)−0.0008 (4)0.0007 (4)−0.0014 (4)
C150.0618 (7)0.0337 (6)0.0537 (7)0.0077 (5)0.0134 (6)0.0041 (5)
C30.0406 (6)0.0400 (6)0.0417 (5)−0.0026 (4)−0.0006 (4)−0.0044 (4)
O10.0492 (5)0.0682 (6)0.0593 (5)−0.0160 (4)0.0177 (4)−0.0100 (5)
C10.0642 (8)0.0620 (8)0.0548 (7)0.0018 (6)0.0188 (6)−0.0020 (6)

Geometric parameters (Å, °)

C8—C91.3369 (17)C11—C101.5174 (15)
C8—C51.4609 (16)C12—C131.3809 (16)
C8—H8A0.9300C6—H6A0.9300
O4—C101.2159 (15)C13—C141.3841 (18)
C5—C41.3951 (16)C13—H13A0.9300
C5—C61.4031 (15)C9—C101.4653 (17)
N1—O31.2168 (14)C9—H9A0.9300
N1—O21.2242 (15)C14—C151.3753 (19)
N1—C121.4674 (14)C14—H14A0.9300
C2—O11.3604 (14)C4—C31.3854 (17)
C2—C31.3846 (16)C4—H4A0.9300
C2—C71.4015 (17)C15—H15A0.9300
C7—C61.3743 (18)C3—H3A0.9300
C7—H7A0.9300O1—C11.4227 (17)
C16—C151.3866 (18)C1—H1A0.9600
C16—C111.3885 (15)C1—H1B0.9600
C16—H16A0.9300C1—H1C0.9600
C11—C121.3929 (15)
C9—C8—C5127.78 (10)C12—C13—H13A120.5
C9—C8—H8A116.1C14—C13—H13A120.5
C5—C8—H8A116.1C8—C9—C10123.72 (10)
C4—C5—C6117.62 (10)C8—C9—H9A118.1
C4—C5—C8119.30 (9)C10—C9—H9A118.1
C6—C5—C8123.02 (10)C15—C14—C13120.22 (11)
O3—N1—O2123.06 (11)C15—C14—H14A119.9
O3—N1—C12118.43 (10)C13—C14—H14A119.9
O2—N1—C12118.50 (11)C3—C4—C5121.84 (10)
O1—C2—C3124.96 (11)C3—C4—H4A119.1
O1—C2—C7115.49 (10)C5—C4—H4A119.1
C3—C2—C7119.55 (11)O4—C10—C9122.22 (11)
C6—C7—C2120.28 (10)O4—C10—C11120.10 (11)
C6—C7—H7A119.9C9—C10—C11117.30 (9)
C2—C7—H7A119.9C14—C15—C16119.96 (11)
C15—C16—C11121.41 (11)C14—C15—H15A120.0
C15—C16—H16A119.3C16—C15—H15A120.0
C11—C16—H16A119.3C2—C3—C4119.58 (10)
C16—C11—C12117.07 (10)C2—C3—H3A120.2
C16—C11—C10116.75 (10)C4—C3—H3A120.2
C12—C11—C10126.14 (9)C2—O1—C1118.75 (10)
C13—C12—C11122.33 (10)O1—C1—H1A109.5
C13—C12—N1117.55 (10)O1—C1—H1B109.5
C11—C12—N1120.05 (10)H1A—C1—H1B109.5
C7—C6—C5121.06 (11)O1—C1—H1C109.5
C7—C6—H6A119.5H1A—C1—H1C109.5
C5—C6—H6A119.5H1B—C1—H1C109.5
C12—C13—C14119.00 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O1i0.932.513.249 (1)136
C14—H14A···O3ii0.932.593.259 (2)129

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2279).

References

  • Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr. 17, 73–80.
  • Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
  • De Vincenzo, R., Ferlini, C. & Distefano, M. (2000). Cancer Chemother. Pharmacol. 46, 305–312. [PubMed]
  • Dimmock, J. R., Kandepu, N. M. & Hetherington, M. (1998). J. Med. Chem. 41, 1014–1026. [PubMed]
  • Fun, H.-K., Chantrapromma, S., Patil, P. S., D’Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954–o955. [PMC free article] [PubMed]
  • Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39–46. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography