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

The title compound, C(25)H(16)O, was prepared by the condens-ation 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 inter-actions, with a perpendicular inter-planar 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 = 332.38

Monoclinic,

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[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 ▶); 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.

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

C25H16O	F000 = 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 = 2.6–25.7º
b = 22.535 (7) Å	µ = 0.08 mm−1
c = 8.250 (3) Å	T = 294 (2) K
β = 106.45 (2)º	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)
Monochromator: graphite	Rint = 0.038
T = 294(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.7º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-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 reflections	Δρmax = 0.11 e Å−3
235 parameters	Δρmin = −0.12 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)