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

Wang, Y.; Wang, Z.; Liang, T.; Fu, H.; Yao, J.

doi:10.1107/S1600536807065476

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o630

doi:10.1107/S1600536807065476

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

Yaobing Wang,^a Zhongliang Wang,^a Tongling Liang,^a Hongbing Fu ^a and Jiannian Yao ^a ^*

^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

(Received 6 November 2007; accepted 4 December 2007; online 27 February 2008)

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 ); Nielsen et al. (2005 ); Pattanaik et al. (2002 ); Strack (1997 ).

Experimental

Crystal data

C₂₅H₁₆O
M_r = 332.38
Monoclinic, P 2₁
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 ) 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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.00
1512 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: 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

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Figures top

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

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

Crystal data top

C₂₅H₁₆O	F(000) = 348
M_r = 332.38	D_x = 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

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1512 independent reflections
Radiation source: fine-focus sealed tube	914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
T_min = 0.981, T_max = 0.991	k = −26→14
3489 measured reflections	l = −9→9

Refinement top

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(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
1512 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₅H₁₆O	V = 833.4 (5) Å³
M_r = 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)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1512 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	914 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.038
3489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.098	H-atom parameters constrained
S = 1.00	Δρ_max = 0.11 e Å⁻³
1512 reflections	Δρ_min = −0.12 e Å⁻³
235 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3489, 1512, 914
R_int	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
Δρ_max, Δρ_min (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

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