organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 8 October 2009; accepted 13 November 2009; online 18 November 2009)

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[Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr. 17, 73-80.]); De Vincenzo et al. (2000[De Vincenzo, R., Ferlini, C. & Distefano, M. (2000). Cancer Chemother. Pharmacol. 46, 305-312.]); Dimmock et al. (1998[Dimmock, J. R., Kandepu, N. M. & Hetherington, M. (1998). J. Med. Chem. 41, 1014-1026.]); Hsieh et al. (1998[Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39-46.]). For a related structure, see: Fun et al. (2008[Fun, H.-K., Chantrapromma, S., Patil, P. S., D'Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954-o955.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13NO4

  • Mr = 283.27

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

For the biological activity of chalcones, see: Anto 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);

Experimental top

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 top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound,viewed along a axis.
3-(4-Methoxyphenyl)-1-(2-nitrophenyl)prop-2-en-1-one top
Crystal data top
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 top
Bruker sMART CCD area-detector
diffractometer
2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
phi and ω scansh = 1515
12773 measured reflectionsk = 108
3107 independent reflectionsl = 1919
Refinement top
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 = 1.08 w = 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
Crystal data top
C16H13NO4V = 1363.1 (5) Å3
Mr = 283.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.594 (2) ŵ = 0.10 mm1
b = 7.7736 (16) ÅT = 293 K
c = 15.174 (3) Å0.21 × 0.18 × 0.10 mm
β = 94.59 (3)°
Data collection top
Bruker sMART CCD area-detector
diffractometer
2667 reflections with I > 2σ(I)
12773 measured reflectionsRint = 0.018
3107 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.08Δρmax = 0.19 e Å3
3107 reflectionsΔρmin = 0.22 e Å3
190 parameters
Special details top

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) top
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)
H9A0.68110.00230.13840.052*
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC16H13NO4
Mr283.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.594 (2), 7.7736 (16), 15.174 (3)
β (°) 94.59 (3)
V3)1363.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.21 × 0.18 × 0.10
Data collection
DiffractometerBruker sMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12773, 3107, 2667
Rint0.018
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.124, 1.08
No. of reflections3107
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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.
 

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

First citationAnto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr. 17, 73–80.  CrossRef CAS Google Scholar
First citationBruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDe Vincenzo, R., Ferlini, C. & Distefano, M. (2000). Cancer Chemother. Pharmacol. 46, 305–312.  Web of Science CrossRef PubMed CAS Google Scholar
First citationDimmock, J. R., Kandepu, N. M. & Hetherington, M. (1998). J. Med. Chem. 41, 1014–1026.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationFun, H.-K., Chantrapromma, S., Patil, P. S., D'Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954–o955.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39–46.  Web of Science CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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