(E)-1-[4-(Prop-2-yn-1-yl-oxy)phen-yl]-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

The mol-ecule of the title chalcone derivative, C(21)H(20)O(5), consists of two substituted aromatic rings bridged by a prop-2-en-1-one group. The dihedral angle between the two benzene rings is 28.7 (7)°. In the crystal, mol-ecules are linked into C(10) chains running along the a axis by inter-molecular C-H⋯O hydrogen bonds, and the chains are cross-linked via C-H⋯π inter-actions.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Rao et al. (2004 ▶); Sabzevari et al. (2004 ▶); Litkei (1979 ▶); Pandey et al. (2005 ▶); Lawrence et al. (2001 ▶); Lin et al. (2002 ▶). For related structures, see: Suwunwong et al. (2009 ▶); Wu et al. (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H20O5

M = 352.37

Monoclinic,

a = 11.6344 (8) Å

b = 11.5970 (7) Å

c = 14.4169 (12) Å

β = 107.763 (5)°

V = 1852.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

17592 measured reflections

4556 independent reflections

3382 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.03

4556 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031193/bt5297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031193/bt5297Isup2.hkl

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

C21H20O5	F(000) = 744
Mr = 352.37	Dx = 1.263 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4556 reflections
a = 11.6344 (8) Å	θ = 2.0–28.3°
b = 11.5970 (7) Å	µ = 0.09 mm−1
c = 14.4169 (12) Å	T = 293 K
β = 107.763 (5)°	Block, white crystalline
V = 1852.5 (2) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4556 independent reflections
Radiation source: fine-focus sealed tube	3382 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
Tmin = 0.981, Tmax = 0.985	k = −13→15
17592 measured reflections	l = −19→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.061P)2 + 0.372P] where P = (Fo2 + 2Fc2)/3
4556 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.66574 (17)	0.75233 (16)	0.97300 (13)	0.0626 (4)
C2	0.62260 (15)	0.70881 (13)	0.89685 (11)	0.0515 (4)
C3	0.56205 (15)	0.65629 (13)	0.80251 (11)	0.0537 (4)
H3A	0.4755	0.6554	0.7911	0.064*
H3B	0.5786	0.7004	0.7509	0.064*
C4	0.55619 (14)	0.47568 (12)	0.72216 (9)	0.0448 (3)
C5	0.46132 (14)	0.51032 (13)	0.64241 (10)	0.0475 (3)
H5	0.4257	0.5822	0.6419	0.057*
C6	0.42044 (13)	0.43671 (13)	0.56392 (10)	0.0466 (3)
H6	0.3566	0.4598	0.5107	0.056*
C7	0.47225 (12)	0.32897 (12)	0.56250 (10)	0.0413 (3)
C8	0.56578 (14)	0.29515 (13)	0.64418 (11)	0.0496 (4)
H8	0.6010	0.2230	0.6450	0.059*
C9	0.60697 (15)	0.36650 (13)	0.72363 (11)	0.0525 (4)
H9	0.6684	0.3421	0.7781	0.063*
C10	0.42741 (13)	0.25699 (12)	0.47322 (10)	0.0437 (3)
C11	0.50561 (13)	0.16440 (12)	0.45563 (10)	0.0440 (3)
H11	0.5799	0.1498	0.5016	0.053*
C12	0.47078 (13)	0.10202 (11)	0.37496 (10)	0.0433 (3)
H12	0.3920	0.1139	0.3355	0.052*
C13	0.54076 (12)	0.01680 (11)	0.34013 (9)	0.0385 (3)
C14	0.49568 (12)	−0.01780 (11)	0.24300 (10)	0.0411 (3)
H14	0.4206	0.0082	0.2047	0.049*
C15	0.56300 (12)	−0.09099 (11)	0.20353 (9)	0.0384 (3)
C16	0.67466 (12)	−0.13097 (11)	0.26139 (9)	0.0373 (3)
C17	0.71902 (12)	−0.09784 (11)	0.35925 (9)	0.0378 (3)
C18	0.65216 (12)	−0.02431 (11)	0.39853 (9)	0.0389 (3)
H18	0.6814	−0.0024	0.4636	0.047*
C19	0.41300 (14)	−0.09359 (15)	0.04783 (11)	0.0557 (4)
H19A	0.3518	−0.1213	0.0743	0.084*
H19B	0.3999	−0.1253	−0.0161	0.084*
H19C	0.4094	−0.0110	0.0438	0.084*
C20	0.73073 (19)	−0.32061 (14)	0.24124 (15)	0.0709 (5)
H20A	0.7478	−0.3316	0.3101	0.106*
H20B	0.7867	−0.3647	0.2186	0.106*
H20C	0.6499	−0.3457	0.2083	0.106*
C21	0.88002 (15)	−0.10781 (15)	0.50787 (11)	0.0560 (4)
H21A	0.8881	−0.0254	0.5118	0.084*
H21B	0.9580	−0.1428	0.5342	0.084*
H21C	0.8280	−0.1327	0.5445	0.084*
O1	0.60592 (11)	0.54149 (9)	0.80317 (7)	0.0595 (3)
O2	0.33027 (10)	0.27793 (11)	0.41288 (9)	0.0656 (3)
O3	0.52865 (9)	−0.12805 (9)	0.10934 (7)	0.0508 (3)
O4	0.74235 (9)	−0.20129 (9)	0.22148 (7)	0.0471 (3)
O5	0.82941 (9)	−0.14134 (9)	0.40858 (7)	0.0513 (3)
H1	0.6977 (17)	0.7866 (17)	1.0333 (15)	0.081 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0697 (11)	0.0595 (10)	0.0548 (10)	0.0012 (8)	0.0136 (8)	−0.0162 (8)
C2	0.0608 (9)	0.0438 (8)	0.0507 (8)	0.0022 (7)	0.0183 (7)	−0.0053 (6)
C3	0.0695 (10)	0.0430 (8)	0.0446 (8)	0.0057 (7)	0.0114 (7)	−0.0059 (6)
C4	0.0563 (8)	0.0421 (7)	0.0354 (6)	0.0020 (6)	0.0133 (6)	−0.0037 (5)
C5	0.0540 (8)	0.0393 (7)	0.0469 (7)	0.0079 (6)	0.0120 (6)	−0.0060 (6)
C6	0.0440 (8)	0.0470 (8)	0.0461 (7)	0.0050 (6)	0.0098 (6)	−0.0068 (6)
C7	0.0416 (7)	0.0409 (7)	0.0447 (7)	−0.0006 (6)	0.0182 (6)	−0.0073 (6)
C8	0.0623 (9)	0.0397 (7)	0.0478 (8)	0.0110 (7)	0.0185 (7)	−0.0008 (6)
C9	0.0627 (9)	0.0499 (8)	0.0403 (7)	0.0129 (7)	0.0085 (7)	−0.0003 (6)
C10	0.0413 (7)	0.0422 (7)	0.0507 (8)	−0.0013 (6)	0.0185 (6)	−0.0099 (6)
C11	0.0436 (7)	0.0417 (7)	0.0489 (7)	0.0035 (6)	0.0176 (6)	−0.0060 (6)
C12	0.0442 (7)	0.0384 (7)	0.0506 (7)	0.0023 (6)	0.0195 (6)	−0.0047 (6)
C13	0.0439 (7)	0.0328 (6)	0.0431 (7)	−0.0010 (5)	0.0198 (6)	−0.0042 (5)
C14	0.0397 (7)	0.0394 (7)	0.0439 (7)	0.0017 (6)	0.0125 (6)	−0.0047 (5)
C15	0.0436 (7)	0.0360 (6)	0.0361 (6)	−0.0032 (5)	0.0130 (5)	−0.0056 (5)
C16	0.0440 (7)	0.0315 (6)	0.0398 (6)	0.0017 (5)	0.0179 (5)	−0.0037 (5)
C17	0.0442 (7)	0.0322 (6)	0.0377 (6)	0.0022 (5)	0.0134 (5)	0.0011 (5)
C18	0.0494 (8)	0.0360 (6)	0.0334 (6)	0.0003 (5)	0.0158 (5)	−0.0031 (5)
C19	0.0524 (9)	0.0623 (10)	0.0454 (8)	−0.0042 (7)	0.0047 (7)	−0.0069 (7)
C20	0.0933 (14)	0.0419 (9)	0.0845 (13)	0.0139 (9)	0.0375 (11)	−0.0095 (8)
C21	0.0565 (9)	0.0602 (9)	0.0436 (8)	0.0056 (8)	0.0038 (7)	−0.0048 (7)
O1	0.0829 (8)	0.0467 (6)	0.0391 (5)	0.0131 (5)	0.0040 (5)	−0.0076 (4)
O2	0.0459 (6)	0.0703 (8)	0.0715 (8)	0.0109 (5)	0.0043 (5)	−0.0307 (6)
O3	0.0498 (6)	0.0608 (6)	0.0380 (5)	0.0056 (5)	0.0077 (4)	−0.0136 (4)
O4	0.0528 (6)	0.0460 (6)	0.0470 (5)	0.0071 (4)	0.0218 (4)	−0.0092 (4)
O5	0.0522 (6)	0.0549 (6)	0.0414 (5)	0.0158 (5)	0.0063 (4)	−0.0068 (4)

C1—C2	1.173 (2)	C13—C14	1.3960 (18)
C1—H1	0.92 (2)	C13—C18	1.3965 (19)
C2—C3	1.460 (2)	C14—C15	1.3890 (18)
C3—O1	1.4248 (18)	C14—H14	0.9300
C3—H3A	0.9700	C15—O3	1.3628 (15)
C3—H3B	0.9700	C15—C16	1.3918 (19)
C4—O1	1.3670 (16)	C16—O4	1.3758 (15)
C4—C5	1.388 (2)	C16—C17	1.4001 (17)
C4—C9	1.395 (2)	C17—O5	1.3610 (16)
C5—C6	1.3810 (19)	C17—C18	1.3862 (17)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.3901 (19)	C19—O3	1.4242 (18)
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.394 (2)	C19—H19B	0.9600
C7—C10	1.4886 (18)	C19—H19C	0.9600
C8—C9	1.375 (2)	C20—O4	1.428 (2)
C8—H8	0.9300	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—O2	1.2220 (18)	C20—H20C	0.9600
C10—C11	1.4784 (18)	C21—O5	1.4256 (17)
C11—C12	1.3239 (19)	C21—H21A	0.9600
C11—H11	0.9300	C21—H21B	0.9600
C12—C13	1.4632 (17)	C21—H21C	0.9600
C12—H12	0.9300
C2—C1—H1	178.4 (12)	C15—C14—C13	120.02 (12)
C1—C2—C3	176.70 (18)	C15—C14—H14	120.0
O1—C3—C2	108.27 (12)	C13—C14—H14	120.0
O1—C3—H3A	110.0	O3—C15—C14	124.77 (12)
C2—C3—H3A	110.0	O3—C15—C16	115.37 (11)
O1—C3—H3B	110.0	C14—C15—C16	119.86 (12)
C2—C3—H3B	110.0	O4—C16—C15	119.71 (11)
H3A—C3—H3B	108.4	O4—C16—C17	120.13 (12)
O1—C4—C5	124.63 (13)	C15—C16—C17	120.15 (11)
O1—C4—C9	115.27 (12)	O5—C17—C18	124.90 (11)
C5—C4—C9	120.09 (13)	O5—C17—C16	115.08 (11)
C6—C5—C4	119.20 (13)	C18—C17—C16	120.01 (12)
C6—C5—H5	120.4	C17—C18—C13	119.80 (11)
C4—C5—H5	120.4	C17—C18—H18	120.1
C5—C6—C7	121.68 (13)	C13—C18—H18	120.1
C5—C6—H6	119.2	O3—C19—H19A	109.5
C7—C6—H6	119.2	O3—C19—H19B	109.5
C6—C7—C8	118.08 (12)	H19A—C19—H19B	109.5
C6—C7—C10	118.53 (13)	O3—C19—H19C	109.5
C8—C7—C10	123.37 (12)	H19A—C19—H19C	109.5
C9—C8—C7	121.21 (13)	H19B—C19—H19C	109.5
C9—C8—H8	119.4	O4—C20—H20A	109.5
C7—C8—H8	119.4	O4—C20—H20B	109.5
C8—C9—C4	119.68 (14)	H20A—C20—H20B	109.5
C8—C9—H9	120.2	O4—C20—H20C	109.5
C4—C9—H9	120.2	H20A—C20—H20C	109.5
O2—C10—C11	120.41 (12)	H20B—C20—H20C	109.5
O2—C10—C7	120.54 (12)	O5—C21—H21A	109.5
C11—C10—C7	118.94 (12)	O5—C21—H21B	109.5
C12—C11—C10	120.54 (13)	H21A—C21—H21B	109.5
C12—C11—H11	119.7	O5—C21—H21C	109.5
C10—C11—H11	119.7	H21A—C21—H21C	109.5
C11—C12—C13	128.12 (13)	H21B—C21—H21C	109.5
C11—C12—H12	115.9	C4—O1—C3	117.30 (11)
C13—C12—H12	115.9	C15—O3—C19	117.78 (11)
C14—C13—C18	120.15 (12)	C16—O4—C20	112.95 (12)
C14—C13—C12	117.40 (12)	C17—O5—C21	117.28 (11)
C18—C13—C12	122.34 (12)
O1—C4—C5—C6	178.74 (14)	C13—C14—C15—C16	0.9 (2)
C9—C4—C5—C6	−1.7 (2)	O3—C15—C16—O4	1.05 (18)
C4—C5—C6—C7	−0.3 (2)	C14—C15—C16—O4	−178.49 (12)
C5—C6—C7—C8	1.6 (2)	O3—C15—C16—C17	179.73 (12)
C5—C6—C7—C10	−176.90 (14)	C14—C15—C16—C17	0.2 (2)
C6—C7—C8—C9	−0.8 (2)	O4—C16—C17—O5	−0.82 (18)
C10—C7—C8—C9	177.62 (14)	C15—C16—C17—O5	−179.50 (12)
C7—C8—C9—C4	−1.3 (2)	O4—C16—C17—C18	178.14 (12)
O1—C4—C9—C8	−177.92 (14)	C15—C16—C17—C18	−0.53 (19)
C5—C4—C9—C8	2.5 (2)	O5—C17—C18—C13	178.66 (12)
C6—C7—C10—O2	−17.5 (2)	C16—C17—C18—C13	−0.19 (19)
C8—C7—C10—O2	164.17 (15)	C14—C13—C18—C17	1.3 (2)
C6—C7—C10—C11	158.74 (13)	C12—C13—C18—C17	−174.75 (12)
C8—C7—C10—C11	−19.6 (2)	C5—C4—O1—C3	−4.2 (2)
O2—C10—C11—C12	−0.9 (2)	C9—C4—O1—C3	176.24 (14)
C7—C10—C11—C12	−177.07 (13)	C2—C3—O1—C4	177.33 (13)
C10—C11—C12—C13	172.41 (13)	C14—C15—O3—C19	−3.0 (2)
C11—C12—C13—C14	−165.06 (14)	C16—C15—O3—C19	177.52 (12)
C11—C12—C13—C18	11.1 (2)	C15—C16—O4—C20	−98.73 (16)
C18—C13—C14—C15	−1.6 (2)	C17—C16—O4—C20	82.59 (17)
C12—C13—C14—C15	174.59 (12)	C18—C17—O5—C21	−0.5 (2)
C13—C14—C15—O3	−178.61 (13)	C16—C17—O5—C21	178.43 (12)

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.42	2.7710 (19)	102
C19—H19A···O2i	0.96	2.48	3.396 (2)	161
C20—H20B···Cg1ii	0.96	2.61	3.487 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O2i	0.96	2.48	3.396 (2)	161
C20—H20B⋯Cg1ii	0.96	2.61	3.487 (2)	152

Symmetry codes: (i) ; (ii) .