1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(18)O(4), 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 = 298.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.108

S = 1.01

2581 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040227/hb5119Isup2.hkl

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

C18H18O4	F(000) = 632
Mr = 298.32	Dx = 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

Bruker SMART CCD diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2037 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.989, Tmax = 0.995	k = −17→16
7545 measured reflections	l = −13→13

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(Fo2) + (0.0725P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2581 reflections	Δρmax = 0.13 e Å−3
203 parameters	Δρmin = −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)

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
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)

	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)

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)