1-Phenyl-3-(2,4,6-trimethoxy­phen­yl)prop-2-en-1-one

Liu, Y.; Zhang, X.; Xue, Z.; Lv, C.

doi:10.1107/S1600536809040227

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2724

https://doi.org/10.1107/S1600536809040227

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: 1-Phenyl-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Ying Liu,^a ^* Xianxi Zhang,^a Zechun Xue ^a and Chunyan Lv ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: yllctu@yahoo.com.cn

(Received 25 September 2009; accepted 2 October 2009; online 13 October 2009)

In the title compound, C₁₈H₁₈O₄, the dihedral angle between the mean planes of the aromatic rings is 7.39 (6)°. The dihedral angles between the linking C—C=C—C plane and the phenyl and benzene rings are 11.27 (5) and 4.20 (5)°, respectively.

Related literature

For background to the properties and applications of chalcones, see: Satish et al., (1995 ), Meng et al., (2004 ), Indira et al., (2002 ). For the synthesis, see: Migrdichian (1957 ).

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.32
Monoclinic, P 2₁ /c
a = 8.8921 (10) Å
b = 15.114 (3) Å
c = 11.618 (3) Å
β = 104.289 (10)°
V = 1513.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.12 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.989, T_max = 0.995
7545 measured reflections
2581 independent reflections
2037 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.108
S = 1.01
2581 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809040227/hb5119sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040227/hb5119Isup2.hkl

checkCIF report

Comment top

In recent years, chalcones consisting of –C=C—C(O)- group have been widely researched due to their interesting properties, such as photoreaction (Satish et al., 1995), biological activity (Meng et al., 2004) and non-linear optical properties (Indira et al., 2002). Herein, we report the synthesis and structure of the title compound.

As shown in figure 1, the C(1)—C(6) phenyl ring is taken as plane 1, another C(10)—C(15) one as plane 2 and the central C(7)—C(8)=C(9)—C(10) as plane 3, with the dihedral angles between them, A12, A13 and A23, of 7.39, 11.27 and 4.20 °, respectively, showing the two phenyl rings are rotated oppositely with respect to the central part of plane 3. The torsional angle C(7)—C(8)=C(9)—C(10) is 177.5 ° and the phenone O(1) atom deviates from plane 3 by 0.13 Å, suggesting C=O is not coplanar with this plane.

Related literature top

For background on the properties and applications of chalcones, see: Satish et al., (1995), Meng et al., (2004), Indira et al., (2002). For the synthesis, see: Migrdichian (1957).

Experimental top

The synthesis of the title compound was according to the related literature (Migrdichian et al., (1957)). An aqueous solution of sodium hydroxide (10%, 10 ml) was added to the mixture of acetophenone (0.02 mol) and 2,4,6-trimethoxyphenylaldehyde (0.02 mol) in 95% ethanol (30 ml). The reaction mixture was stirred at room temperature for 5 h, yielding light yellow solid neutralized by hydrochloric acid (10%) and water. Colourless blocks of (I) were obtained by slow evaporation from dry ethanol. Elemental Analysis. Calc. for C₁₈H₁₈O₄: C 72.41, H 6.03%; Found: C 72.38, H 6.01%.

Structure description top

For background on the properties and applications of chalcones, see: Satish et al., (1995), Meng et al., (2004), Indira et al., (2002). For the synthesis, see: Migrdichian (1957).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms.

1-Phenyl-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₈O₄	F(000) = 632
M_r = 298.32	D_x = 1.310 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2581 reflections
a = 8.8921 (10) Å	θ = 2.4–25.0°
b = 15.114 (3) Å	µ = 0.09 mm⁻¹
c = 11.618 (3) Å	T = 293 K
β = 104.289 (10)°	Block, colourless
V = 1513.1 (5) Å³	0.12 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.989, T_max = 0.995	k = −17→16
7545 measured reflections	l = −13→13

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0725P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2581 reflections	Δρ_max = 0.13 e Å⁻³
203 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.329 (18)

Crystal data top

C₁₈H₁₈O₄	V = 1513.1 (5) Å³
M_r = 298.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8921 (10) Å	µ = 0.09 mm⁻¹
b = 15.114 (3) Å	T = 293 K
c = 11.618 (3) Å	0.12 × 0.10 × 0.05 mm
β = 104.289 (10)°

Data collection top

Bruker SMART CCD diffractometer	2581 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2037 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.995	R_int = 0.037
7545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	Δρ_max = 0.13 e Å⁻³
2581 reflections	Δρ_min = −0.13 e Å⁻³
203 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
C1	−0.14370 (15)	0.24856 (10)	0.22992 (12)	0.0564 (4)
H1	−0.1511	0.2141	0.2946	0.068*
C2	−0.25419 (15)	0.31225 (11)	0.18742 (14)	0.0645 (4)
H2	−0.3356	0.3200	0.2236	0.077*
C3	−0.24594 (16)	0.36410 (11)	0.09297 (14)	0.0653 (4)
H3	−0.3202	0.4076	0.0659	0.078*
C4	−0.12883 (17)	0.35171 (10)	0.03889 (13)	0.0654 (4)
H4	−0.1228	0.3865	−0.0258	0.078*
C5	−0.01819 (15)	0.28718 (9)	0.08018 (12)	0.0550 (4)
H5	0.0607	0.2784	0.0417	0.066*
C6	−0.02275 (13)	0.23540 (9)	0.17773 (10)	0.0463 (3)
C7	0.09868 (14)	0.16867 (9)	0.23099 (11)	0.0505 (3)
C8	0.22237 (14)	0.15192 (9)	0.17349 (11)	0.0505 (4)
H8	0.2182	0.1777	0.1001	0.061*
C9	0.34224 (14)	0.10042 (8)	0.22297 (10)	0.0452 (3)
H9	0.3361	0.0743	0.2941	0.054*
C10	0.47889 (13)	0.07856 (8)	0.18512 (10)	0.0405 (3)
C11	0.51540 (14)	0.11331 (8)	0.08352 (10)	0.0431 (3)
C12	0.64572 (14)	0.08891 (8)	0.05099 (10)	0.0474 (3)
H12	0.6667	0.1122	−0.0175	0.057*
C13	0.74710 (13)	0.02941 (8)	0.11969 (11)	0.0460 (3)
C14	0.72008 (13)	−0.00523 (8)	0.22196 (10)	0.0457 (3)
H14	0.7900	−0.0443	0.2688	0.055*
C15	0.58727 (13)	0.01938 (8)	0.25291 (10)	0.0422 (3)
C16	0.65272 (16)	−0.07565 (10)	0.42236 (11)	0.0592 (4)
H16A	0.6572	−0.1275	0.3757	0.089*
H16B	0.6140	−0.0913	0.4898	0.089*
H16C	0.7548	−0.0509	0.4491	0.089*
C17	0.44269 (17)	0.21138 (9)	−0.08152 (12)	0.0616 (4)
H17A	0.5398	0.2424	−0.0602	0.092*
H17B	0.3610	0.2521	−0.1157	0.092*
H17C	0.4479	0.1661	−0.1383	0.092*
C18	0.97451 (18)	−0.05696 (11)	0.14022 (14)	0.0733 (5)
H18A	1.0180	−0.0392	0.2209	0.110*
H18B	1.0565	−0.0657	0.1009	0.110*
H18C	0.9181	−0.1112	0.1393	0.110*
O1	0.55255 (10)	−0.01251 (6)	0.35230 (8)	0.0566 (3)
O2	0.41252 (10)	0.17263 (6)	0.02034 (7)	0.0574 (3)
O3	0.87224 (10)	0.01005 (7)	0.08024 (8)	0.0639 (3)
O4	0.09522 (11)	0.13301 (8)	0.32405 (9)	0.0787 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0473 (7)	0.0676 (9)	0.0567 (8)	−0.0009 (6)	0.0171 (6)	−0.0055 (7)
C2	0.0418 (7)	0.0773 (10)	0.0776 (10)	0.0068 (7)	0.0208 (7)	−0.0089 (8)
C3	0.0514 (8)	0.0694 (10)	0.0725 (10)	0.0144 (7)	0.0104 (7)	−0.0030 (8)
C4	0.0649 (9)	0.0683 (9)	0.0623 (9)	0.0123 (7)	0.0144 (7)	0.0046 (7)
C5	0.0487 (7)	0.0644 (9)	0.0541 (8)	0.0055 (6)	0.0166 (6)	−0.0045 (6)
C6	0.0375 (6)	0.0555 (7)	0.0446 (7)	−0.0005 (5)	0.0076 (5)	−0.0105 (6)
C7	0.0428 (7)	0.0661 (8)	0.0415 (7)	0.0028 (6)	0.0083 (5)	−0.0058 (6)
C8	0.0442 (7)	0.0645 (8)	0.0422 (7)	0.0074 (6)	0.0093 (5)	−0.0014 (6)
C9	0.0439 (7)	0.0519 (7)	0.0395 (6)	0.0012 (6)	0.0097 (5)	−0.0049 (5)
C10	0.0392 (6)	0.0437 (7)	0.0379 (6)	0.0010 (5)	0.0081 (5)	−0.0025 (5)
C11	0.0436 (7)	0.0430 (7)	0.0402 (6)	0.0021 (5)	0.0059 (5)	0.0008 (5)
C12	0.0513 (7)	0.0519 (7)	0.0413 (7)	0.0007 (6)	0.0158 (6)	0.0063 (5)
C13	0.0420 (6)	0.0506 (7)	0.0484 (7)	0.0031 (5)	0.0169 (5)	0.0025 (6)
C14	0.0428 (7)	0.0478 (7)	0.0475 (7)	0.0064 (5)	0.0131 (6)	0.0073 (5)
C15	0.0428 (7)	0.0467 (7)	0.0380 (6)	−0.0013 (5)	0.0115 (5)	0.0022 (5)
C16	0.0574 (8)	0.0705 (9)	0.0505 (8)	0.0117 (7)	0.0149 (6)	0.0197 (7)
C17	0.0695 (9)	0.0633 (9)	0.0503 (8)	0.0047 (7)	0.0117 (7)	0.0161 (6)
C18	0.0631 (9)	0.0874 (11)	0.0802 (10)	0.0323 (8)	0.0385 (8)	0.0277 (9)
O1	0.0515 (5)	0.0748 (6)	0.0479 (5)	0.0156 (5)	0.0209 (4)	0.0201 (4)
O2	0.0562 (6)	0.0661 (6)	0.0504 (5)	0.0162 (4)	0.0140 (4)	0.0177 (4)
O3	0.0564 (6)	0.0799 (7)	0.0647 (6)	0.0207 (5)	0.0328 (5)	0.0226 (5)
O4	0.0661 (7)	0.1169 (9)	0.0584 (6)	0.0289 (6)	0.0255 (5)	0.0239 (6)

Geometric parameters (Å, º) top

C1—C6	1.3733 (18)	C11—C12	1.3556 (17)
C1—C2	1.3770 (19)	C12—C13	1.3797 (17)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.365 (2)	C13—O3	1.3362 (14)
C2—H2	0.9300	C13—C14	1.3727 (17)
C3—C4	1.355 (2)	C14—C15	1.3682 (15)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.3843 (19)	C15—O1	1.3554 (14)
C4—H4	0.9300	C16—O1	1.4172 (15)
C5—C6	1.3860 (18)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.4954 (18)	C16—H16C	0.9600
C7—O4	1.2153 (16)	C17—O2	1.4044 (15)
C7—C8	1.4431 (17)	C17—H17A	0.9600
C8—C9	1.3305 (17)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C10	1.4292 (16)	C18—O3	1.4232 (16)
C9—H9	0.9300	C18—H18A	0.9600
C10—C11	1.4014 (16)	C18—H18B	0.9600
C10—C15	1.4051 (16)	C18—H18C	0.9600
C11—O2	1.3594 (14)

C6—C1—C2	120.67 (13)	C11—C12—C13	119.83 (11)
C6—C1—H1	119.7	C11—C12—H12	120.1
C2—C1—H1	119.7	C13—C12—H12	120.1
C3—C2—C1	120.96 (13)	O3—C13—C14	123.49 (11)
C3—C2—H2	119.5	O3—C13—C12	115.14 (11)
C1—C2—H2	119.5	C14—C13—C12	121.36 (11)
C4—C3—C2	119.55 (14)	C15—C14—C13	118.08 (11)
C4—C3—H3	120.2	C15—C14—H14	121.0
C2—C3—H3	120.2	C13—C14—H14	121.0
C3—C4—C5	119.89 (14)	O1—C15—C14	121.34 (11)
C3—C4—H4	120.1	O1—C15—C10	115.78 (10)
C5—C4—H4	120.1	C14—C15—C10	122.88 (10)
C4—C5—C6	121.29 (12)	O1—C16—H16A	109.5
C4—C5—H5	119.4	O1—C16—H16B	109.5
C6—C5—H5	119.4	H16A—C16—H16B	109.5
C1—C6—C5	117.61 (12)	O1—C16—H16C	109.5
C1—C6—C7	118.63 (12)	H16A—C16—H16C	109.5
C5—C6—C7	123.73 (11)	H16B—C16—H16C	109.5
O4—C7—C8	121.57 (12)	O2—C17—H17A	109.5
O4—C7—C6	119.54 (12)	O2—C17—H17B	109.5
C8—C7—C6	118.80 (11)	H17A—C17—H17B	109.5
C9—C8—C7	121.57 (12)	O2—C17—H17C	109.5
C9—C8—H8	119.2	H17A—C17—H17C	109.5
C7—C8—H8	119.2	H17B—C17—H17C	109.5
C8—C9—C10	130.82 (12)	O3—C18—H18A	109.5
C8—C9—H9	114.6	O3—C18—H18B	109.5
C10—C9—H9	114.6	H18A—C18—H18B	109.5
C11—C10—C15	116.18 (10)	O3—C18—H18C	109.5
C11—C10—C9	124.32 (11)	H18A—C18—H18C	109.5
C15—C10—C9	119.49 (10)	H18B—C18—H18C	109.5
O2—C11—C12	122.44 (11)	C15—O1—C16	119.06 (9)
O2—C11—C10	115.92 (10)	C11—O2—C17	119.14 (10)
C12—C11—C10	121.64 (11)	C13—O3—C18	118.25 (10)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₄
M_r	298.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.8921 (10), 15.114 (3), 11.618 (3)
β (°)	104.289 (10)
V (Å³)	1513.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.989, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	7545, 2581, 2037
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.108, 1.01
No. of reflections	2581
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Acknowledgements

The work was supported by Liaocheng University (grant No. X071011) and the National Ministry of Science and Technology of China (grant No. 20501011).

References

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