1-(4-Methoxy­phen­yl)-5-phenyl­penta-2,4-dien-1-one

In the crystal structure of the title compound, C₁₈H₁₆O₂, the mol­ecules related by a c-glide plane are linked into a column running along the c axis by a weak inter­molecular C—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.094
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.08 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), was synthesized because it was expected to have a big π conjugation system which is potentially useful in the photoelectric fields and the crystal engineering. The methoxy group attached to the benzene ring deviates slightly from the molecular plane with the torsion angle of C18—O2—C15—C16 = -0.59 (2)°. The related compound, 1-phenyl-5-phenylpenta-2,4-dien-1-one (Zhao et al., 1999), is more planar than its substituted derivatives (Vorontsova et al., 1973) and the present compound.

In the crystal structure, the molecules stack along the c axis through a very week C—H···O hydrogen bond (Table 1).

Related literature

For related literature, see: Charles & Morris (1955); Vorontsova & Kazaryan (1973); Zhao et al. (1999).

S2. Experimental

The title compound was prepared according to the literature procedure of Charles & Morris (1955). The crude product was recrystallized several times from ethanol

and the yellow single crystals were obtained by slow evaporation of a ethanol solution (m.p. 369–371 K). Analysis calculated for C₁₈H₁₆O₂: C 81.79, H 6.10%; found: C 81.60, H 5.99%.

S3. Refinement

All H atoms were positioned geometrically (C—H = 0.93 - 0.96 Å) and refined as riding, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level.

1-(4-MMethoxyphenyl)-5-phenylpenta-2,4-dien-1-one

Crystal data

C18H16O2	F(000) = 560
Mr = 264.31	Dx = 1.209 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 28 reflections
a = 12.004 (2) Å	θ = 2.7–15.7°
b = 15.727 (2) Å	µ = 0.08 mm^−1
c = 8.077 (1) Å	T = 297 K
β = 107.83 (1)°	Block, yellow
V = 1451.6 (4) Å^3	0.54 × 0.50 × 0.24 mm
Z = 4

Data collection

Siemens P4 diffractometer	Rint = 0.014
Radiation source: normal-focus sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = −14→13
ω scans	k = −18→0
2974 measured reflections	l = 0→9
2560 independent reflections	3 standard reflections every 970 reflections
1439 reflections with I > 2σ(I)	intensity decay: 2.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0495P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max = 0.001
2560 reflections	Δρmax = 0.15 e Å^−3
183 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0139 (15)

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.19411 (9)	0.10710 (7)	−0.09462 (16)	0.0779 (4)
O2	0.73397 (9)	0.17972 (7)	0.04888 (15)	0.0754 (4)
C1	−0.09513 (15)	0.47096 (11)	0.1517 (2)	0.0735 (5)
H1	−0.0145	0.4676	0.2027	0.088*
C2	−0.15599 (19)	0.53658 (12)	0.1957 (3)	0.0891 (6)
H2	−0.1163	0.5769	0.2765	0.107*
C3	−0.2744 (2)	0.54324 (14)	0.1218 (3)	0.0949 (7)
H3	−0.3151	0.5879	0.1521	0.114*
C4	−0.33271 (18)	0.48377 (17)	0.0028 (3)	0.0975 (7)
H4	−0.4131	0.4883	−0.0491	0.117*
C5	−0.27211 (16)	0.41723 (13)	−0.0401 (2)	0.0819 (6)
H5	−0.3126	0.3766	−0.1194	0.098*
C6	−0.15188 (14)	0.40975 (11)	0.0328 (2)	0.0616 (4)
C7	−0.09118 (14)	0.33810 (10)	−0.0168 (2)	0.0655 (5)
H7	−0.1380	0.2972	−0.0884	0.079*
C8	0.02322 (13)	0.32510 (10)	0.0292 (2)	0.0622 (4)
H8	0.0711	0.3661	0.0990	0.075*
C9	0.07948 (14)	0.25328 (11)	−0.0195 (2)	0.0619 (4)
H9	0.0322	0.2112	−0.0864	0.074*
C10	0.19482 (13)	0.24269 (11)	0.0243 (2)	0.0637 (4)
H10	0.2424	0.2839	0.0938	0.076*
C11	0.25122 (14)	0.17021 (10)	−0.0299 (2)	0.0588 (4)
C12	0.37840 (13)	0.17344 (9)	−0.00920 (19)	0.0529 (4)
C13	0.45110 (14)	0.23974 (10)	0.0734 (2)	0.0643 (5)
H13	0.4197	0.2849	0.1188	0.077*
C14	0.56818 (14)	0.23975 (11)	0.0891 (2)	0.0680 (5)
H14	0.6151	0.2847	0.1449	0.082*
C15	0.61673 (14)	0.17356 (10)	0.0229 (2)	0.0583 (4)
C16	0.54681 (15)	0.10737 (10)	−0.0613 (2)	0.0620 (4)
H16	0.5786	0.0627	−0.1075	0.074*
C17	0.42928 (14)	0.10812 (10)	−0.0762 (2)	0.0607 (4)
H17	0.3825	0.0633	−0.1331	0.073*
C18	0.79246 (15)	0.11007 (12)	0.0003 (3)	0.0913 (6)
H18A	0.7779	0.0594	0.0566	0.110*
H18B	0.8751	0.1211	0.0350	0.110*
H18C	0.7639	0.1026	−0.1235	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0749 (8)	0.0590 (8)	0.0965 (9)	−0.0060 (6)	0.0216 (7)	−0.0063 (7)
O2	0.0646 (7)	0.0727 (8)	0.0924 (9)	0.0057 (6)	0.0294 (6)	−0.0050 (7)
C1	0.0682 (11)	0.0671 (11)	0.0934 (14)	−0.0034 (10)	0.0368 (10)	−0.0038 (11)
C2	0.0998 (16)	0.0662 (13)	0.1164 (17)	−0.0003 (11)	0.0553 (14)	−0.0053 (12)
C3	0.1090 (18)	0.0872 (16)	0.1075 (18)	0.0339 (13)	0.0611 (15)	0.0227 (14)
C4	0.0766 (14)	0.137 (2)	0.0822 (15)	0.0354 (14)	0.0297 (12)	0.0191 (15)
C5	0.0672 (12)	0.1093 (16)	0.0706 (12)	0.0114 (11)	0.0234 (10)	−0.0019 (11)
C6	0.0599 (11)	0.0667 (11)	0.0634 (11)	0.0034 (9)	0.0267 (9)	0.0090 (9)
C7	0.0639 (11)	0.0676 (11)	0.0667 (11)	−0.0031 (9)	0.0223 (9)	−0.0034 (9)
C8	0.0605 (11)	0.0678 (11)	0.0618 (11)	−0.0028 (9)	0.0239 (9)	−0.0032 (9)
C9	0.0669 (11)	0.0615 (10)	0.0607 (10)	−0.0009 (9)	0.0245 (8)	0.0011 (9)
C10	0.0633 (11)	0.0670 (11)	0.0616 (11)	−0.0022 (9)	0.0203 (8)	−0.0063 (9)
C11	0.0681 (11)	0.0527 (11)	0.0548 (10)	0.0020 (9)	0.0177 (8)	0.0043 (8)
C12	0.0631 (10)	0.0467 (9)	0.0496 (9)	0.0015 (8)	0.0185 (8)	0.0031 (8)
C13	0.0675 (11)	0.0600 (11)	0.0686 (11)	0.0046 (9)	0.0254 (9)	−0.0138 (9)
C14	0.0694 (11)	0.0649 (11)	0.0699 (12)	−0.0060 (9)	0.0214 (9)	−0.0165 (9)
C15	0.0618 (11)	0.0585 (11)	0.0566 (10)	0.0074 (9)	0.0210 (8)	0.0056 (8)
C16	0.0748 (11)	0.0456 (9)	0.0694 (11)	0.0084 (8)	0.0278 (9)	0.0008 (8)
C17	0.0724 (11)	0.0460 (9)	0.0640 (11)	0.0005 (8)	0.0215 (9)	0.0007 (8)
C18	0.0735 (12)	0.0849 (14)	0.1222 (17)	0.0179 (11)	0.0398 (12)	0.0016 (12)

Geometric parameters (Å, º)

O1—C11	1.2283 (17)	C9—C10	1.3303 (19)
O2—C15	1.3613 (17)	C9—H9	0.930
O2—C18	1.4196 (19)	C10—C11	1.460 (2)
C1—C2	1.372 (2)	C10—H10	0.930
C1—C6	1.383 (2)	C11—C12	1.485 (2)
C1—H1	0.930	C12—C17	1.387 (2)
C2—C3	1.367 (3)	C12—C13	1.392 (2)
C2—H2	0.930	C13—C14	1.372 (2)
C3—C4	1.370 (3)	C13—H13	0.930
C3—H3	0.930	C14—C15	1.379 (2)
C4—C5	1.378 (3)	C14—H14	0.930
C4—H4	0.930	C15—C16	1.379 (2)
C5—C6	1.387 (2)	C16—C17	1.379 (2)
C5—H5	0.930	C16—H16	0.930
C6—C7	1.463 (2)	C17—H17	0.930
C7—C8	1.3242 (19)	C18—H18A	0.960
C7—H7	0.930	C18—H18B	0.960
C8—C9	1.432 (2)	C18—H18C	0.960
C8—H8	0.930
C15—O2—C18	118.55 (13)	O1—C11—C10	120.58 (15)
C2—C1—C6	121.00 (18)	O1—C11—C12	119.76 (14)
C2—C1—H1	119.4	C10—C11—C12	119.65 (14)
C3—C2—C1	120.6 (2)	C17—C12—C13	117.09 (14)
C3—C2—H2	119.6	C17—C12—C11	119.41 (14)
C2—C3—C4	119.6 (2)	C13—C12—C11	123.50 (14)
C2—C3—H3	120.2	C14—C13—C12	121.25 (15)
C3—C4—C5	119.9 (2)	C14—C13—H13	119.3
C3—C4—H4	120.1	C13—C14—C15	120.44 (16)
C4—C5—C6	121.2 (2)	C13—C14—H14	119.8
C4—C5—H5	119.3	O2—C15—C14	115.23 (15)
C1—C6—C5	117.59 (16)	O2—C15—C16	125.05 (14)
C1—C6—C7	123.07 (15)	C14—C15—C16	119.72 (15)
C5—C6—C7	119.34 (16)	C15—C16—C17	119.24 (15)
C8—C7—C6	127.08 (16)	C15—C16—H16	120.4
C8—C7—H7	116.5	C16—C17—C12	122.24 (15)
C7—C8—C9	125.50 (16)	C16—C17—H17	119.0
C7—C8—H8	117.3	C15—O2—C18	118.57 (14)
C10—C9—C8	124.43 (16)	H18A—C18—H18B	109.5
C10—C9—H9	117.8	H18A—C18—H18C	109.5
C9—C10—C11	123.93 (16)	H18B—C18—H18C	109.5
C9—C10—H10	118.0
C6—C1—C2—C3	−0.4 (3)	C10—C11—C12—C17	−173.78 (14)
C1—C2—C3—C4	0.0 (3)	O1—C11—C12—C13	−175.43 (15)
C2—C3—C4—C5	0.8 (3)	C10—C11—C12—C13	5.5 (2)
C3—C4—C5—C6	−1.2 (3)	C17—C12—C13—C14	−0.7 (2)
C2—C1—C6—C5	0.0 (2)	C11—C12—C13—C14	−179.97 (15)
C2—C1—C6—C7	−179.27 (16)	C12—C13—C14—C15	0.0 (2)
C4—C5—C6—C1	0.8 (3)	C18—O2—C15—C14	173.68 (15)
C4—C5—C6—C7	−179.90 (16)	C18—O2—C15—C16	−5.9 (2)
C1—C6—C7—C8	−6.5 (3)	C13—C14—C15—O2	−178.89 (14)
C5—C6—C7—C8	174.21 (16)	C13—C14—C15—C16	0.7 (2)
C6—C7—C8—C9	178.84 (14)	O2—C15—C16—C17	178.82 (14)
C7—C8—C9—C10	178.09 (16)	C14—C15—C16—C17	−0.7 (2)
C8—C9—C10—C11	−178.35 (14)	C15—C16—C17—C12	0.0 (2)
C9—C10—C11—O1	−13.0 (2)	C13—C12—C17—C16	0.6 (2)
C9—C10—C11—C12	166.06 (15)	C11—C12—C17—C16	179.98 (14)
O1—C11—C12—C17	5.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.50	3.280 (2)	142

Symmetry code: (i) x, −y+1/2, z+1/2.