(E)-1,5-Di-phenyl-pent-2-en-4-yn-1-one.

The title compound, C17H12O, has an E conformation about the C=C bond. The C-C C-C torsion angle is 7.7 (2)°, and the mean planes of the phenyl-ethyl-enone [r.m.s. deviation = 0.059 (1) Å] and phenyl-acetyl-ene [r.m.s. deviation = 0.023 (1) Å] fragments form a dihedral angle of 14.16 (7)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into zigzag chains propagated in [010].

Related literature

For the synthesis and properties of enynones, see: Toshima et al. (1999 ▶); Ohe et al. (2002 ▶); Miki et al. (2002 ▶); Kuroda et al. (2004 ▶); Casey & Strotman (2005 ▶). For the crystal structures of related compounds, see: König et al. (1995 ▶); Chen & Liu (2008 ▶); Lu et al. (2009 ▶).

Experimental

Crystal data

C17H12O

M = 232.27

Orthorhombic,

a = 5.4696 (4) Å

b = 13.7164 (10) Å

c = 16.3117 (11) Å

V = 1223.76 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.977, T max = 0.985

15765 measured reflections

3576 independent reflections

2987 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.107

S = 1.07

3576 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013044/cv5408sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013044/cv5408Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013044/cv5408Isup3.cml

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

C17H12O	F(000) = 488
Mr = 232.27	Dx = 1.261 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2940 reflections
a = 5.4696 (4) Å	θ = 2.5–31.0°
b = 13.7164 (10) Å	µ = 0.08 mm−1
c = 16.3117 (11) Å	T = 120 K
V = 1223.76 (15) Å3	Prism, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker APEXII CCD diffractometer	3576 independent reflections
Radiation source: fine-focus sealed tube	2987 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→7
Tmin = 0.977, Tmax = 0.985	k = −19→19
15765 measured reflections	l = −22→22

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.3124P] where P = (Fo2 + 2Fc2)/3
3576 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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	0.1245 (3)	0.55925 (10)	0.38879 (8)	0.0335 (4)
C1	0.2582 (3)	0.54777 (13)	0.44784 (10)	0.0206 (4)
C2	0.4701 (4)	0.48088 (14)	0.44289 (11)	0.0256 (4)
H2	0.5833	0.4784	0.4870	0.031*
C3	0.5045 (3)	0.42448 (13)	0.37800 (11)	0.0244 (4)
H3	0.3930	0.4310	0.3337	0.029*
C4	0.6951 (3)	0.35500 (13)	0.36950 (11)	0.0236 (4)
C5	0.8456 (3)	0.29185 (13)	0.36230 (10)	0.0220 (4)
C6	0.2084 (3)	0.60079 (12)	0.52645 (11)	0.0186 (3)
C7	−0.0018 (3)	0.65863 (13)	0.53149 (11)	0.0229 (4)
H7	−0.1086	0.6634	0.4857	0.027*
C8	−0.0548 (3)	0.70902 (13)	0.60295 (11)	0.0243 (4)
H8	−0.1989	0.7474	0.6062	0.029*
C9	0.1022 (3)	0.70358 (13)	0.66981 (12)	0.0252 (4)
H9	0.0661	0.7386	0.7186	0.030*
C10	0.3109 (4)	0.64699 (14)	0.66512 (12)	0.0259 (4)
H10	0.4186	0.6434	0.7107	0.031*
C11	0.3639 (3)	0.59521 (13)	0.59370 (11)	0.0210 (4)
H11	0.5069	0.5560	0.5910	0.025*
C12	1.0198 (3)	0.21457 (12)	0.35339 (10)	0.0198 (4)
C13	1.2102 (4)	0.20245 (14)	0.40995 (11)	0.0239 (4)
H13	1.2228	0.2451	0.4557	0.029*
C14	1.3797 (4)	0.12875 (13)	0.39951 (12)	0.0265 (4)
H14	1.5079	0.1207	0.4382	0.032*
C15	1.3632 (4)	0.06627 (13)	0.33257 (12)	0.0254 (4)
H15	1.4813	0.0162	0.3253	0.031*
C16	1.1752 (3)	0.07688 (13)	0.27652 (11)	0.0240 (4)
H16	1.1632	0.0337	0.2312	0.029*
C17	1.0046 (3)	0.15044 (13)	0.28663 (10)	0.0213 (4)
H17	0.8760	0.1576	0.2480	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0380 (8)	0.0373 (8)	0.0251 (7)	0.0140 (7)	−0.0102 (6)	−0.0036 (6)
C1	0.0223 (9)	0.0184 (8)	0.0211 (8)	−0.0014 (7)	0.0001 (7)	0.0016 (7)
C2	0.0276 (10)	0.0249 (9)	0.0242 (9)	0.0061 (8)	−0.0026 (8)	−0.0011 (8)
C3	0.0264 (9)	0.0247 (9)	0.0222 (9)	0.0025 (8)	0.0001 (8)	0.0028 (7)
C4	0.0277 (9)	0.0242 (9)	0.0190 (8)	−0.0007 (8)	0.0016 (8)	0.0004 (7)
C5	0.0261 (9)	0.0226 (8)	0.0174 (8)	−0.0030 (8)	0.0037 (7)	−0.0017 (7)
C6	0.0194 (8)	0.0154 (8)	0.0211 (8)	−0.0025 (7)	0.0028 (7)	0.0020 (6)
C7	0.0219 (9)	0.0209 (9)	0.0258 (9)	0.0018 (8)	−0.0007 (8)	0.0035 (7)
C8	0.0215 (9)	0.0192 (9)	0.0323 (10)	0.0016 (7)	0.0049 (8)	0.0005 (8)
C9	0.0268 (10)	0.0209 (9)	0.0278 (9)	−0.0029 (8)	0.0050 (8)	−0.0056 (8)
C10	0.0253 (9)	0.0286 (9)	0.0237 (9)	−0.0024 (8)	−0.0024 (8)	−0.0033 (8)
C11	0.0178 (8)	0.0208 (8)	0.0246 (9)	0.0013 (7)	0.0005 (7)	0.0001 (7)
C12	0.0235 (9)	0.0186 (8)	0.0172 (8)	−0.0030 (7)	0.0055 (7)	0.0013 (6)
C13	0.0280 (9)	0.0243 (9)	0.0194 (8)	−0.0031 (8)	−0.0001 (7)	0.0000 (7)
C14	0.0227 (9)	0.0268 (10)	0.0300 (10)	−0.0027 (8)	−0.0068 (8)	0.0058 (8)
C15	0.0221 (9)	0.0223 (9)	0.0319 (10)	0.0031 (8)	0.0027 (8)	0.0020 (8)
C16	0.0276 (10)	0.0214 (9)	0.0230 (9)	−0.0012 (8)	0.0031 (8)	−0.0018 (7)
C17	0.0218 (9)	0.0229 (9)	0.0193 (8)	−0.0015 (8)	−0.0002 (7)	0.0021 (7)

O1—C1	1.220 (2)	C9—H9	0.9500
C1—C2	1.480 (3)	C10—C11	1.395 (2)
C1—C6	1.499 (2)	C10—H10	0.9500
C2—C3	1.324 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.401 (2)
C3—C4	1.419 (3)	C12—C17	1.402 (2)
C3—H3	0.9500	C13—C14	1.382 (3)
C4—C5	1.201 (3)	C13—H13	0.9500
C5—C12	1.432 (2)	C14—C15	1.391 (3)
C6—C11	1.390 (2)	C14—H14	0.9500
C6—C7	1.399 (2)	C15—C16	1.384 (3)
C7—C8	1.386 (2)	C15—H15	0.9500
C7—H7	0.9500	C16—C17	1.384 (3)
C8—C9	1.390 (3)	C16—H16	0.9500
C8—H8	0.9500	C17—H17	0.9500
C9—C10	1.383 (3)
O1—C1—C2	120.42 (16)	C9—C10—H10	119.9
O1—C1—C6	120.26 (16)	C11—C10—H10	119.9
C2—C1—C6	119.33 (16)	C6—C11—C10	120.25 (17)
C3—C2—C1	121.14 (17)	C6—C11—H11	119.9
C3—C2—H2	119.4	C10—C11—H11	119.9
C1—C2—H2	119.4	C13—C12—C17	118.73 (17)
C2—C3—C4	125.09 (18)	C13—C12—C5	121.01 (16)
C2—C3—H3	117.5	C17—C12—C5	120.25 (16)
C4—C3—H3	117.5	C14—C13—C12	120.28 (17)
C5—C4—C3	176.0 (2)	C14—C13—H13	119.9
C4—C5—C12	178.4 (2)	C12—C13—H13	119.9
C11—C6—C7	119.19 (16)	C13—C14—C15	120.25 (17)
C11—C6—C1	122.47 (16)	C13—C14—H14	119.9
C7—C6—C1	118.34 (16)	C15—C14—H14	119.9
C8—C7—C6	120.27 (17)	C16—C15—C14	120.14 (18)
C8—C7—H7	119.9	C16—C15—H15	119.9
C6—C7—H7	119.9	C14—C15—H15	119.9
C7—C8—C9	120.27 (17)	C15—C16—C17	119.92 (17)
C7—C8—H8	119.9	C15—C16—H16	120.0
C9—C8—H8	119.9	C17—C16—H16	120.0
C10—C9—C8	119.78 (17)	C16—C17—C12	120.67 (17)
C10—C9—H9	120.1	C16—C17—H17	119.7
C8—C9—H9	120.1	C12—C17—H17	119.7
C9—C10—C11	120.24 (18)
O1—C1—C2—C3	−7.3 (3)	C8—C9—C10—C11	−0.2 (3)
C6—C1—C2—C3	172.28 (18)	C7—C6—C11—C10	−0.2 (3)
C1—C2—C3—C4	−176.86 (17)	C1—C6—C11—C10	179.16 (17)
O1—C1—C6—C11	−175.68 (18)	C9—C10—C11—C6	0.6 (3)
C2—C1—C6—C11	4.8 (3)	C17—C12—C13—C14	0.3 (3)
O1—C1—C6—C7	3.7 (3)	C5—C12—C13—C14	−178.64 (17)
C2—C1—C6—C7	−175.85 (16)	C12—C13—C14—C15	0.3 (3)
C3—C4—C5—C12	7.7 (2)	C13—C14—C15—C16	−0.7 (3)
C11—C6—C7—C8	−0.5 (3)	C14—C15—C16—C17	0.7 (3)
C1—C6—C7—C8	−179.91 (17)	C15—C16—C17—C12	−0.1 (3)
C6—C7—C8—C9	0.9 (3)	C13—C12—C17—C16	−0.3 (3)
C7—C8—C9—C10	−0.5 (3)	C5—C12—C17—C16	178.58 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.95	2.54	3.165 (2)	124
C17—H17···O1i	0.95	2.61	3.202 (2)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.95	2.54	3.165 (2)	124
C17—H17⋯O1i	0.95	2.61	3.202 (2)	121

Symmetry code: (i) .