organic compounds
1-Phenyl-3-(pyren-1-yl)prop-2-en-1-one
aBeijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People's Republic of China
*Correspondence e-mail: jnyao@iccas.ac.cn
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 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); Nielsen et al. (2005); Pattanaik et al. (2002); Strack (1997).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536807065476/rz2180sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536807065476/rz2180Isup2.hkl
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.
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
effects, Friedel pairs were merged in the final refinement.Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL (Sheldrick, 1990).Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C25H16O | F(000) = 348 |
Mr = 332.38 | Dx = 1.324 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 824 reflections |
a = 4.6739 (15) Å | θ = 2.6–25.7° |
b = 22.535 (7) Å | µ = 0.08 mm−1 |
c = 8.250 (3) Å | T = 294 K |
β = 106.45 (2)° | Block, yellow |
V = 833.4 (5) Å3 | 0.24 × 0.22 × 0.12 mm |
Z = 2 |
Bruker SMART 1K CCD area-detector diffractometer | 1512 independent reflections |
Radiation source: fine-focus sealed tube | 914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −5→5 |
Tmin = 0.981, Tmax = 0.991 | k = −26→14 |
3489 measured reflections | l = −9→9 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3 |
1512 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.11 e Å−3 |
1 restraint | Δρmin = −0.12 e Å−3 |
C25H16O | V = 833.4 (5) Å3 |
Mr = 332.38 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.6739 (15) Å | µ = 0.08 mm−1 |
b = 22.535 (7) Å | T = 294 K |
c = 8.250 (3) Å | 0.24 × 0.22 × 0.12 mm |
β = 106.45 (2)° |
Bruker SMART 1K CCD area-detector diffractometer | 1512 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 914 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.991 | Rint = 0.038 |
3489 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 1 restraint |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.11 e Å−3 |
1512 reflections | Δρmin = −0.12 e Å−3 |
235 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 | ||
O1 | 1.0978 (8) | 0.06540 (14) | 0.3854 (4) | 0.0865 (10) | |
C1 | 0.2634 (8) | 0.31864 (18) | 0.6348 (5) | 0.0474 (10) | |
C2 | 0.4014 (8) | 0.30397 (17) | 0.5070 (5) | 0.0456 (10) | |
C3 | 0.5149 (8) | 0.24553 (17) | 0.4986 (5) | 0.0437 (9) | |
C4 | 0.4779 (8) | 0.20312 (18) | 0.6221 (5) | 0.0532 (11) | |
H4 | 0.5470 | 0.1646 | 0.6191 | 0.064* | |
C5 | 0.3463 (9) | 0.21795 (19) | 0.7411 (5) | 0.0558 (11) | |
H5 | 0.3277 | 0.1892 | 0.8184 | 0.067* | |
C6 | 0.2339 (8) | 0.27586 (18) | 0.7539 (5) | 0.0507 (10) | |
C7 | 0.0951 (9) | 0.2918 (2) | 0.8760 (6) | 0.0676 (12) | |
H7 | 0.0754 | 0.2637 | 0.9547 | 0.081* | |
C8 | −0.0129 (11) | 0.3477 (2) | 0.8831 (6) | 0.0781 (15) | |
H8 | −0.1058 | 0.3572 | 0.9656 | 0.094* | |
C9 | 0.0158 (9) | 0.3905 (2) | 0.7673 (6) | 0.0706 (14) | |
H9 | −0.0569 | 0.4286 | 0.7736 | 0.085* | |
C10 | 0.1518 (9) | 0.37699 (19) | 0.6421 (5) | 0.0561 (11) | |
C11 | 0.1810 (9) | 0.4196 (2) | 0.5191 (6) | 0.0657 (13) | |
H11 | 0.1079 | 0.4578 | 0.5231 | 0.079* | |
C12 | 0.3107 (9) | 0.40594 (19) | 0.3987 (6) | 0.0619 (12) | |
H12 | 0.3263 | 0.4347 | 0.3208 | 0.074* | |
C13 | 0.4260 (8) | 0.34749 (15) | 0.3881 (5) | 0.0481 (10) | |
C14 | 0.5642 (9) | 0.33242 (19) | 0.2671 (5) | 0.0555 (11) | |
H14 | 0.5841 | 0.3610 | 0.1897 | 0.067* | |
C15 | 0.6733 (9) | 0.27656 (17) | 0.2572 (5) | 0.0542 (11) | |
H15 | 0.7622 | 0.2680 | 0.1723 | 0.065* | |
C16 | 0.6540 (8) | 0.23186 (16) | 0.3724 (5) | 0.0460 (10) | |
C17 | 0.7838 (9) | 0.17355 (17) | 0.3629 (5) | 0.0527 (10) | |
H17 | 0.7879 | 0.1477 | 0.4513 | 0.063* | |
C18 | 0.8963 (9) | 0.15305 (17) | 0.2438 (5) | 0.0585 (11) | |
H18 | 0.8827 | 0.1765 | 0.1491 | 0.070* | |
C19 | 1.0416 (9) | 0.09496 (19) | 0.2545 (6) | 0.0561 (11) | |
C20 | 1.1212 (8) | 0.07115 (16) | 0.1054 (5) | 0.0486 (9) | |
C21 | 1.3317 (9) | 0.0265 (2) | 0.1272 (5) | 0.0617 (11) | |
H21 | 1.4290 | 0.0135 | 0.2357 | 0.074* | |
C22 | 1.3998 (10) | 0.00115 (19) | −0.0091 (7) | 0.0751 (14) | |
H22 | 1.5397 | −0.0293 | 0.0076 | 0.090* | |
C23 | 1.2618 (11) | 0.0207 (2) | −0.1689 (6) | 0.0732 (13) | |
H23 | 1.3094 | 0.0040 | −0.2611 | 0.088* | |
C24 | 1.0536 (11) | 0.0648 (2) | −0.1928 (5) | 0.0740 (13) | |
H24 | 0.9581 | 0.0777 | −0.3018 | 0.089* | |
C25 | 0.9834 (11) | 0.09030 (18) | −0.0569 (5) | 0.0632 (13) | |
H25 | 0.8426 | 0.1206 | −0.0747 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.123 (3) | 0.079 (2) | 0.0604 (19) | 0.027 (2) | 0.0325 (18) | 0.0182 (18) |
C1 | 0.035 (2) | 0.059 (3) | 0.043 (2) | −0.0053 (19) | 0.0029 (18) | −0.007 (2) |
C2 | 0.038 (2) | 0.055 (3) | 0.042 (2) | −0.0131 (19) | 0.0081 (19) | −0.0036 (19) |
C3 | 0.037 (2) | 0.054 (3) | 0.037 (2) | −0.0056 (19) | 0.0062 (18) | 0.0029 (19) |
C4 | 0.057 (3) | 0.056 (3) | 0.048 (2) | −0.004 (2) | 0.017 (2) | 0.004 (2) |
C5 | 0.056 (3) | 0.065 (3) | 0.047 (3) | −0.009 (2) | 0.015 (2) | 0.007 (2) |
C6 | 0.042 (2) | 0.068 (3) | 0.041 (2) | −0.007 (2) | 0.0105 (19) | −0.003 (2) |
C7 | 0.056 (3) | 0.093 (4) | 0.054 (3) | −0.003 (3) | 0.016 (2) | −0.006 (2) |
C8 | 0.068 (3) | 0.107 (5) | 0.064 (3) | −0.001 (3) | 0.026 (3) | −0.018 (3) |
C9 | 0.054 (3) | 0.085 (4) | 0.069 (3) | 0.001 (2) | 0.011 (3) | −0.029 (3) |
C10 | 0.045 (2) | 0.065 (3) | 0.054 (3) | −0.005 (2) | 0.008 (2) | −0.016 (2) |
C11 | 0.056 (3) | 0.054 (3) | 0.078 (3) | 0.004 (2) | 0.005 (3) | −0.002 (2) |
C12 | 0.060 (3) | 0.051 (3) | 0.072 (3) | −0.003 (2) | 0.014 (3) | 0.008 (2) |
C13 | 0.041 (2) | 0.051 (3) | 0.050 (2) | −0.0058 (19) | 0.009 (2) | 0.003 (2) |
C14 | 0.061 (3) | 0.056 (3) | 0.051 (3) | −0.006 (2) | 0.019 (2) | 0.015 (2) |
C15 | 0.059 (3) | 0.061 (3) | 0.045 (2) | −0.007 (2) | 0.018 (2) | −0.001 (2) |
C16 | 0.047 (2) | 0.047 (3) | 0.044 (2) | −0.009 (2) | 0.012 (2) | 0.000 (2) |
C17 | 0.058 (2) | 0.055 (3) | 0.046 (2) | −0.004 (2) | 0.015 (2) | −0.001 (2) |
C18 | 0.077 (3) | 0.053 (3) | 0.049 (2) | 0.004 (2) | 0.022 (2) | 0.006 (2) |
C19 | 0.058 (3) | 0.056 (3) | 0.053 (3) | 0.000 (2) | 0.013 (2) | 0.004 (2) |
C20 | 0.057 (2) | 0.041 (2) | 0.050 (2) | −0.005 (2) | 0.0174 (19) | −0.0035 (19) |
C21 | 0.065 (3) | 0.057 (2) | 0.058 (3) | −0.002 (2) | 0.009 (2) | 0.001 (2) |
C22 | 0.073 (3) | 0.062 (3) | 0.091 (4) | 0.007 (3) | 0.026 (3) | −0.015 (3) |
C23 | 0.082 (4) | 0.074 (3) | 0.070 (3) | 0.000 (3) | 0.031 (3) | −0.011 (3) |
C24 | 0.099 (4) | 0.069 (3) | 0.054 (3) | 0.017 (3) | 0.023 (3) | 0.001 (2) |
C25 | 0.086 (3) | 0.052 (3) | 0.051 (3) | 0.017 (2) | 0.020 (3) | 0.003 (2) |
O1—C19 | 1.232 (5) | C12—H12 | 0.9300 |
C1—C6 | 1.411 (5) | C13—C14 | 1.377 (5) |
C1—C2 | 1.422 (4) | C14—C15 | 1.369 (5) |
C1—C10 | 1.422 (6) | C14—H14 | 0.9300 |
C2—C13 | 1.414 (5) | C15—C16 | 1.405 (5) |
C2—C3 | 1.429 (5) | C15—H15 | 0.9300 |
C3—C16 | 1.409 (5) | C16—C17 | 1.459 (5) |
C3—C4 | 1.443 (5) | C17—C18 | 1.322 (5) |
C4—C5 | 1.340 (5) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.466 (5) |
C5—C6 | 1.422 (5) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.483 (5) |
C6—C7 | 1.391 (5) | C20—C25 | 1.380 (5) |
C7—C8 | 1.364 (6) | C20—C21 | 1.382 (5) |
C7—H7 | 0.9300 | C21—C22 | 1.377 (5) |
C8—C9 | 1.390 (6) | C21—H21 | 0.9300 |
C8—H8 | 0.9300 | C22—C23 | 1.366 (6) |
C9—C10 | 1.392 (5) | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C23—C24 | 1.365 (6) |
C10—C11 | 1.431 (6) | C23—H23 | 0.9300 |
C11—C12 | 1.338 (6) | C24—C25 | 1.381 (5) |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—C13 | 1.435 (5) | C25—H25 | 0.9300 |
C6—C1—C2 | 120.8 (3) | C2—C13—C12 | 119.2 (4) |
C6—C1—C10 | 119.5 (4) | C15—C14—C13 | 121.9 (4) |
C2—C1—C10 | 119.7 (4) | C15—C14—H14 | 119.0 |
C13—C2—C1 | 119.7 (3) | C13—C14—H14 | 119.0 |
C13—C2—C3 | 120.1 (3) | C14—C15—C16 | 121.5 (4) |
C1—C2—C3 | 120.2 (3) | C14—C15—H15 | 119.2 |
C16—C3—C2 | 119.5 (3) | C16—C15—H15 | 119.2 |
C16—C3—C4 | 123.3 (4) | C15—C16—C3 | 118.3 (4) |
C2—C3—C4 | 117.1 (3) | C15—C16—C17 | 120.1 (3) |
C5—C4—C3 | 121.6 (4) | C3—C16—C17 | 121.5 (3) |
C5—C4—H4 | 119.2 | C18—C17—C16 | 127.9 (4) |
C3—C4—H4 | 119.2 | C18—C17—H17 | 116.1 |
C4—C5—C6 | 122.6 (4) | C16—C17—H17 | 116.1 |
C4—C5—H5 | 118.7 | C17—C18—C19 | 122.8 (4) |
C6—C5—H5 | 118.7 | C17—C18—H18 | 118.6 |
C7—C6—C1 | 119.0 (4) | C19—C18—H18 | 118.6 |
C7—C6—C5 | 123.3 (4) | O1—C19—C18 | 121.1 (4) |
C1—C6—C5 | 117.7 (3) | O1—C19—C20 | 119.3 (4) |
C8—C7—C6 | 121.6 (5) | C18—C19—C20 | 119.6 (4) |
C8—C7—H7 | 119.2 | C25—C20—C21 | 118.2 (3) |
C6—C7—H7 | 119.2 | C25—C20—C19 | 122.3 (3) |
C7—C8—C9 | 120.1 (4) | C21—C20—C19 | 119.5 (4) |
C7—C8—H8 | 119.9 | C22—C21—C20 | 121.1 (4) |
C9—C8—H8 | 119.9 | C22—C21—H21 | 119.4 |
C8—C9—C10 | 120.8 (4) | C20—C21—H21 | 119.4 |
C8—C9—H9 | 119.6 | C23—C22—C21 | 119.9 (4) |
C10—C9—H9 | 119.6 | C23—C22—H22 | 120.0 |
C9—C10—C1 | 118.9 (4) | C21—C22—H22 | 120.0 |
C9—C10—C11 | 122.4 (4) | C24—C23—C22 | 119.7 (4) |
C1—C10—C11 | 118.7 (4) | C24—C23—H23 | 120.1 |
C12—C11—C10 | 121.7 (4) | C22—C23—H23 | 120.1 |
C12—C11—H11 | 119.1 | C23—C24—C25 | 120.6 (4) |
C10—C11—H11 | 119.1 | C23—C24—H24 | 119.7 |
C11—C12—C13 | 120.9 (4) | C25—C24—H24 | 119.7 |
C11—C12—H12 | 119.6 | C20—C25—C24 | 120.3 (4) |
C13—C12—H12 | 119.6 | C20—C25—H25 | 119.8 |
C14—C13—C2 | 118.6 (4) | C24—C25—H25 | 119.8 |
C14—C13—C12 | 122.1 (4) | ||
C6—C1—C2—C13 | 179.5 (4) | C3—C2—C13—C14 | −0.9 (5) |
C10—C1—C2—C13 | −0.1 (5) | C1—C2—C13—C12 | 0.0 (5) |
C6—C1—C2—C3 | −0.6 (5) | C3—C2—C13—C12 | −180.0 (3) |
C10—C1—C2—C3 | 179.9 (4) | C11—C12—C13—C14 | −179.1 (4) |
C13—C2—C3—C16 | 0.7 (5) | C11—C12—C13—C2 | 0.0 (6) |
C1—C2—C3—C16 | −179.3 (3) | C2—C13—C14—C15 | 1.0 (6) |
C13—C2—C3—C4 | −179.0 (4) | C12—C13—C14—C15 | −179.8 (4) |
C1—C2—C3—C4 | 1.0 (4) | C13—C14—C15—C16 | −1.1 (6) |
C16—C3—C4—C5 | 179.5 (3) | C14—C15—C16—C3 | 0.8 (6) |
C2—C3—C4—C5 | −0.8 (5) | C14—C15—C16—C17 | −177.4 (4) |
C3—C4—C5—C6 | 0.2 (6) | C2—C3—C16—C15 | −0.7 (5) |
C2—C1—C6—C7 | −179.4 (3) | C4—C3—C16—C15 | 179.0 (3) |
C10—C1—C6—C7 | 0.1 (5) | C2—C3—C16—C17 | 177.5 (3) |
C2—C1—C6—C5 | −0.1 (5) | C4—C3—C16—C17 | −2.8 (6) |
C10—C1—C6—C5 | 179.5 (3) | C15—C16—C17—C18 | −8.4 (6) |
C4—C5—C6—C7 | 179.6 (4) | C3—C16—C17—C18 | 173.5 (4) |
C4—C5—C6—C1 | 0.3 (6) | C16—C17—C18—C19 | 175.2 (4) |
C1—C6—C7—C8 | 0.0 (6) | C17—C18—C19—O1 | −8.9 (6) |
C5—C6—C7—C8 | −179.3 (4) | C17—C18—C19—C20 | 170.8 (4) |
C6—C7—C8—C9 | −0.4 (7) | O1—C19—C20—C25 | 157.8 (4) |
C7—C8—C9—C10 | 0.6 (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—C11 | 179.0 (4) | C18—C19—C20—C21 | 160.8 (4) |
C6—C1—C10—C9 | 0.1 (5) | C25—C20—C21—C22 | −0.9 (6) |
C2—C1—C10—C9 | 179.6 (3) | C19—C20—C21—C22 | 176.5 (4) |
C6—C1—C10—C11 | −179.4 (3) | C20—C21—C22—C23 | 1.1 (7) |
C2—C1—C10—C11 | 0.2 (5) | C21—C22—C23—C24 | −0.9 (7) |
C9—C10—C11—C12 | −179.6 (4) | C22—C23—C24—C25 | 0.7 (7) |
C1—C10—C11—C12 | −0.2 (6) | C21—C20—C25—C24 | 0.7 (6) |
C10—C11—C12—C13 | 0.1 (6) | C19—C20—C25—C24 | −176.7 (4) |
C1—C2—C13—C14 | 179.1 (3) | C23—C24—C25—C20 | −0.6 (7) |
Experimental details
Crystal data | |
Chemical formula | C25H16O |
Mr | 332.38 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 4.6739 (15), 22.535 (7), 8.250 (3) |
β (°) | 106.45 (2) |
V (Å3) | 833.4 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.24 × 0.22 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.981, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3489, 1512, 914 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.098, 1.00 |
No. of reflections | 1512 |
No. of parameters | 235 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.12 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990).
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Nos. 90301010, 50573084, 90606004),
References
Ansari, F. L., Nazira, S., Noureenb, H. & Mirzab, B. (2005). Chem. Biodiversity, 2, 1656–1664. Web of Science CrossRef CAS Google Scholar
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667–2677. Web of Science CrossRef PubMed CAS Google Scholar
Pattanaik, P., Raman, J. & Balaram, H. (2002). Curr. Top. Med. Chem. 2, 438–496. CrossRef Google Scholar
Sheldrick, G. M. (1990). SHELXTL/PC. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Strack, D. (1997). In Plant Biochemistry, p. 387. San Diego: Academic Press. Google Scholar
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.
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.