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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o630.
Published online 2008 February 27. doi:  10.1107/S1600536807065476
PMCID: PMC2960839

1-Phenyl-3-(pyren-1-yl)prop-2-en-1-one

Abstract

The title compound, C25H16O, was prepared by the condens­ation reaction of pyrene-1-carbaldehyde and acetophenone in ethanol solution at room temperature. The phenyl ring forms a dihedral angle of 39.10 (11)° with the pyrene ring system. In the crystal structure, adjacent pyrene ring systems are linked by aromatic π–π stacking inter­actions, with a perpendicular inter­planar distance of 3.267 (6) Å and a centroid–centroid offset of 2.946 (7) Å.

Related literature

For related literature, see: Ansari et al. (2005 [triangle]); Nielsen et al. (2005 [triangle]); Pattanaik et al. (2002 [triangle]); Strack (1997 [triangle]).

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Object name is e-64-0o630-scheme1.jpg

Experimental

Crystal data

  • C25H16O
  • M r = 332.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o630-efi1.jpg
  • a = 4.6739 (15) Å
  • b = 22.535 (7) Å
  • c = 8.250 (3) Å
  • β = 106.45 (2)°
  • V = 833.4 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 294 (2) K
  • 0.24 × 0.22 × 0.12 mm

Data collection

  • Bruker SMART 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.981, T max = 0.991
  • 3489 measured reflections
  • 1512 independent reflections
  • 914 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.098
  • S = 1.00
  • 1512 reflections
  • 235 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Sheldrick, 1990 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065476/rz2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065476/rz2180Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Nos. 90301010, 50573084, 90606004),

supplementary crystallographic information

Comment

Chalcone derivatives have always been of interest in the field of inorganic, organic and physical chemists and biology (Strack, 1997) due to their importance in many organic synthetic pathways, biochemical processes and enzymatic mechanisms (Ansari et al., 2005; Pattanaik et al., 2002; Nielsen et al., 2005). In this paper, we report the crystal structure of the title compound, which was obtained by the condensation reaction of pyrene-1-carbaldehyde and acetophenone in ethanol solution at room temperature.

In the title compound, the pyrene ring is substantially planar (maximum displacement 0.011 (4) Å for C12) and forms a dihedral angle of 39.10 (11)° with the phenyl ring. In the crystal packing, adjacent pyrene rings are linked by aromatic π-π stacking interactions, with a centroid-centroid distance of 4.339 (7) Å, a perpendicular interplanar distance of 3.267 (6) Å and a centroid-centroid offset of 2.946 (7) Å.

Experimental

The title compound was prepared by the condensation reaction of pyrene-1-carbaldehyde (0.05 mol) and acetophenone (0.05 mol) in ethanol (20 ml) at room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by slow evaporation of an ethanol/acetonitrile solution (1:1 v/v) at room temperature.

Refinement

All H atoms were fixed geometrically and were treated as riding on the parent C atoms, with C—H distances of 0.93 Å. Uiso(H) = 1.2 Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged in the final refinement.

Figures

Fig. 1.
The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C25H16OF000 = 348
Mr = 332.38Dx = 1.324 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 824 reflections
a = 4.6739 (15) Åθ = 2.6–25.7º
b = 22.535 (7) ŵ = 0.08 mm1
c = 8.250 (3) ÅT = 294 (2) K
β = 106.45 (2)ºBlock, yellow
V = 833.4 (5) Å30.24 × 0.22 × 0.12 mm
Z = 2

Data collection

Bruker SMART 1K CCD area-detector diffractometer1512 independent reflections
Radiation source: fine-focus sealed tube914 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 2002)h = −5→5
Tmin = 0.981, Tmax = 0.991k = −26→14
3489 measured reflectionsl = −9→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.098  w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1512 reflectionsΔρmax = 0.11 e Å3
235 parametersΔρmin = −0.12 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
O11.0978 (8)0.06540 (14)0.3854 (4)0.0865 (10)
C10.2634 (8)0.31864 (18)0.6348 (5)0.0474 (10)
C20.4014 (8)0.30397 (17)0.5070 (5)0.0456 (10)
C30.5149 (8)0.24553 (17)0.4986 (5)0.0437 (9)
C40.4779 (8)0.20312 (18)0.6221 (5)0.0532 (11)
H40.54700.16460.61910.064*
C50.3463 (9)0.21795 (19)0.7411 (5)0.0558 (11)
H50.32770.18920.81840.067*
C60.2339 (8)0.27586 (18)0.7539 (5)0.0507 (10)
C70.0951 (9)0.2918 (2)0.8760 (6)0.0676 (12)
H70.07540.26370.95470.081*
C8−0.0129 (11)0.3477 (2)0.8831 (6)0.0781 (15)
H8−0.10580.35720.96560.094*
C90.0158 (9)0.3905 (2)0.7673 (6)0.0706 (14)
H9−0.05690.42860.77360.085*
C100.1518 (9)0.37699 (19)0.6421 (5)0.0561 (11)
C110.1810 (9)0.4196 (2)0.5191 (6)0.0657 (13)
H110.10790.45780.52310.079*
C120.3107 (9)0.40594 (19)0.3987 (6)0.0619 (12)
H120.32630.43470.32080.074*
C130.4260 (8)0.34749 (15)0.3881 (5)0.0481 (10)
C140.5642 (9)0.33242 (19)0.2671 (5)0.0555 (11)
H140.58410.36100.18970.067*
C150.6733 (9)0.27656 (17)0.2572 (5)0.0542 (11)
H150.76220.26800.17230.065*
C160.6540 (8)0.23186 (16)0.3724 (5)0.0460 (10)
C170.7838 (9)0.17355 (17)0.3629 (5)0.0527 (10)
H170.78790.14770.45130.063*
C180.8963 (9)0.15305 (17)0.2438 (5)0.0585 (11)
H180.88270.17650.14910.070*
C191.0416 (9)0.09496 (19)0.2545 (6)0.0561 (11)
C201.1212 (8)0.07115 (16)0.1054 (5)0.0486 (9)
C211.3317 (9)0.0265 (2)0.1272 (5)0.0617 (11)
H211.42900.01350.23570.074*
C221.3998 (10)0.00115 (19)−0.0091 (7)0.0751 (14)
H221.5397−0.02930.00760.090*
C231.2618 (11)0.0207 (2)−0.1689 (6)0.0732 (13)
H231.30940.0040−0.26110.088*
C241.0536 (11)0.0648 (2)−0.1928 (5)0.0740 (13)
H240.95810.0777−0.30180.089*
C250.9834 (11)0.09030 (18)−0.0569 (5)0.0632 (13)
H250.84260.1206−0.07470.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.123 (3)0.079 (2)0.0604 (19)0.027 (2)0.0325 (18)0.0182 (18)
C10.035 (2)0.059 (3)0.043 (2)−0.0053 (19)0.0029 (18)−0.007 (2)
C20.038 (2)0.055 (3)0.042 (2)−0.0131 (19)0.0081 (19)−0.0036 (19)
C30.037 (2)0.054 (3)0.037 (2)−0.0056 (19)0.0062 (18)0.0029 (19)
C40.057 (3)0.056 (3)0.048 (2)−0.004 (2)0.017 (2)0.004 (2)
C50.056 (3)0.065 (3)0.047 (3)−0.009 (2)0.015 (2)0.007 (2)
C60.042 (2)0.068 (3)0.041 (2)−0.007 (2)0.0105 (19)−0.003 (2)
C70.056 (3)0.093 (4)0.054 (3)−0.003 (3)0.016 (2)−0.006 (2)
C80.068 (3)0.107 (5)0.064 (3)−0.001 (3)0.026 (3)−0.018 (3)
C90.054 (3)0.085 (4)0.069 (3)0.001 (2)0.011 (3)−0.029 (3)
C100.045 (2)0.065 (3)0.054 (3)−0.005 (2)0.008 (2)−0.016 (2)
C110.056 (3)0.054 (3)0.078 (3)0.004 (2)0.005 (3)−0.002 (2)
C120.060 (3)0.051 (3)0.072 (3)−0.003 (2)0.014 (3)0.008 (2)
C130.041 (2)0.051 (3)0.050 (2)−0.0058 (19)0.009 (2)0.003 (2)
C140.061 (3)0.056 (3)0.051 (3)−0.006 (2)0.019 (2)0.015 (2)
C150.059 (3)0.061 (3)0.045 (2)−0.007 (2)0.018 (2)−0.001 (2)
C160.047 (2)0.047 (3)0.044 (2)−0.009 (2)0.012 (2)0.000 (2)
C170.058 (2)0.055 (3)0.046 (2)−0.004 (2)0.015 (2)−0.001 (2)
C180.077 (3)0.053 (3)0.049 (2)0.004 (2)0.022 (2)0.006 (2)
C190.058 (3)0.056 (3)0.053 (3)0.000 (2)0.013 (2)0.004 (2)
C200.057 (2)0.041 (2)0.050 (2)−0.005 (2)0.0174 (19)−0.0035 (19)
C210.065 (3)0.057 (2)0.058 (3)−0.002 (2)0.009 (2)0.001 (2)
C220.073 (3)0.062 (3)0.091 (4)0.007 (3)0.026 (3)−0.015 (3)
C230.082 (4)0.074 (3)0.070 (3)0.000 (3)0.031 (3)−0.011 (3)
C240.099 (4)0.069 (3)0.054 (3)0.017 (3)0.023 (3)0.001 (2)
C250.086 (3)0.052 (3)0.051 (3)0.017 (2)0.020 (3)0.003 (2)

Geometric parameters (Å, °)

O1—C191.232 (5)C12—H120.9300
C1—C61.411 (5)C13—C141.377 (5)
C1—C21.422 (4)C14—C151.369 (5)
C1—C101.422 (6)C14—H140.9300
C2—C131.414 (5)C15—C161.405 (5)
C2—C31.429 (5)C15—H150.9300
C3—C161.409 (5)C16—C171.459 (5)
C3—C41.443 (5)C17—C181.322 (5)
C4—C51.340 (5)C17—H170.9300
C4—H40.9300C18—C191.466 (5)
C5—C61.422 (5)C18—H180.9300
C5—H50.9300C19—C201.483 (5)
C6—C71.391 (5)C20—C251.380 (5)
C7—C81.364 (6)C20—C211.382 (5)
C7—H70.9300C21—C221.377 (5)
C8—C91.390 (6)C21—H210.9300
C8—H80.9300C22—C231.366 (6)
C9—C101.392 (5)C22—H220.9300
C9—H90.9300C23—C241.365 (6)
C10—C111.431 (6)C23—H230.9300
C11—C121.338 (6)C24—C251.381 (5)
C11—H110.9300C24—H240.9300
C12—C131.435 (5)C25—H250.9300
C6—C1—C2120.8 (3)C2—C13—C12119.2 (4)
C6—C1—C10119.5 (4)C15—C14—C13121.9 (4)
C2—C1—C10119.7 (4)C15—C14—H14119.0
C13—C2—C1119.7 (3)C13—C14—H14119.0
C13—C2—C3120.1 (3)C14—C15—C16121.5 (4)
C1—C2—C3120.2 (3)C14—C15—H15119.2
C16—C3—C2119.5 (3)C16—C15—H15119.2
C16—C3—C4123.3 (4)C15—C16—C3118.3 (4)
C2—C3—C4117.1 (3)C15—C16—C17120.1 (3)
C5—C4—C3121.6 (4)C3—C16—C17121.5 (3)
C5—C4—H4119.2C18—C17—C16127.9 (4)
C3—C4—H4119.2C18—C17—H17116.1
C4—C5—C6122.6 (4)C16—C17—H17116.1
C4—C5—H5118.7C17—C18—C19122.8 (4)
C6—C5—H5118.7C17—C18—H18118.6
C7—C6—C1119.0 (4)C19—C18—H18118.6
C7—C6—C5123.3 (4)O1—C19—C18121.1 (4)
C1—C6—C5117.7 (3)O1—C19—C20119.3 (4)
C8—C7—C6121.6 (5)C18—C19—C20119.6 (4)
C8—C7—H7119.2C25—C20—C21118.2 (3)
C6—C7—H7119.2C25—C20—C19122.3 (3)
C7—C8—C9120.1 (4)C21—C20—C19119.5 (4)
C7—C8—H8119.9C22—C21—C20121.1 (4)
C9—C8—H8119.9C22—C21—H21119.4
C8—C9—C10120.8 (4)C20—C21—H21119.4
C8—C9—H9119.6C23—C22—C21119.9 (4)
C10—C9—H9119.6C23—C22—H22120.0
C9—C10—C1118.9 (4)C21—C22—H22120.0
C9—C10—C11122.4 (4)C24—C23—C22119.7 (4)
C1—C10—C11118.7 (4)C24—C23—H23120.1
C12—C11—C10121.7 (4)C22—C23—H23120.1
C12—C11—H11119.1C23—C24—C25120.6 (4)
C10—C11—H11119.1C23—C24—H24119.7
C11—C12—C13120.9 (4)C25—C24—H24119.7
C11—C12—H12119.6C20—C25—C24120.3 (4)
C13—C12—H12119.6C20—C25—H25119.8
C14—C13—C2118.6 (4)C24—C25—H25119.8
C14—C13—C12122.1 (4)
C6—C1—C2—C13179.5 (4)C3—C2—C13—C14−0.9 (5)
C10—C1—C2—C13−0.1 (5)C1—C2—C13—C120.0 (5)
C6—C1—C2—C3−0.6 (5)C3—C2—C13—C12−180.0 (3)
C10—C1—C2—C3179.9 (4)C11—C12—C13—C14−179.1 (4)
C13—C2—C3—C160.7 (5)C11—C12—C13—C20.0 (6)
C1—C2—C3—C16−179.3 (3)C2—C13—C14—C151.0 (6)
C13—C2—C3—C4−179.0 (4)C12—C13—C14—C15−179.8 (4)
C1—C2—C3—C41.0 (4)C13—C14—C15—C16−1.1 (6)
C16—C3—C4—C5179.5 (3)C14—C15—C16—C30.8 (6)
C2—C3—C4—C5−0.8 (5)C14—C15—C16—C17−177.4 (4)
C3—C4—C5—C60.2 (6)C2—C3—C16—C15−0.7 (5)
C2—C1—C6—C7−179.4 (3)C4—C3—C16—C15179.0 (3)
C10—C1—C6—C70.1 (5)C2—C3—C16—C17177.5 (3)
C2—C1—C6—C5−0.1 (5)C4—C3—C16—C17−2.8 (6)
C10—C1—C6—C5179.5 (3)C15—C16—C17—C18−8.4 (6)
C4—C5—C6—C7179.6 (4)C3—C16—C17—C18173.5 (4)
C4—C5—C6—C10.3 (6)C16—C17—C18—C19175.2 (4)
C1—C6—C7—C80.0 (6)C17—C18—C19—O1−8.9 (6)
C5—C6—C7—C8−179.3 (4)C17—C18—C19—C20170.8 (4)
C6—C7—C8—C9−0.4 (7)O1—C19—C20—C25157.8 (4)
C7—C8—C9—C100.6 (7)C18—C19—C20—C25−21.9 (6)
C8—C9—C10—C1−0.4 (6)O1—C19—C20—C21−19.5 (6)
C8—C9—C10—C11179.0 (4)C18—C19—C20—C21160.8 (4)
C6—C1—C10—C90.1 (5)C25—C20—C21—C22−0.9 (6)
C2—C1—C10—C9179.6 (3)C19—C20—C21—C22176.5 (4)
C6—C1—C10—C11−179.4 (3)C20—C21—C22—C231.1 (7)
C2—C1—C10—C110.2 (5)C21—C22—C23—C24−0.9 (7)
C9—C10—C11—C12−179.6 (4)C22—C23—C24—C250.7 (7)
C1—C10—C11—C12−0.2 (6)C21—C20—C25—C240.7 (6)
C10—C11—C12—C130.1 (6)C19—C20—C25—C24−176.7 (4)
C1—C2—C13—C14179.1 (3)C23—C24—C25—C20−0.6 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2180).

References

  • Ansari, F. L., Nazira, S., Noureenb, H. & Mirzab, B. (2005). Chem. Biodiversity, 2, 1656–1664. [PubMed]
  • Bruker (2002). SMART, SAINT and SADABS Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem.48, 2667–2677. [PubMed]
  • Pattanaik, P., Raman, J. & Balaram, H. (2002). Curr. Top. Med. Chem.2, 438–496. [PubMed]
  • Sheldrick, G. M. (1990). SHELXTL/PC Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Strack, D. (1997). In Plant Biochemistry, p. 387. San Diego: Academic Press.

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