(E)-3-(4-Heptyl-oxyphen-yl)-1-phenyl-prop-2-en-1-one.

In the title compound, C22H26O2, the aromatic rings are inclined to one another by 8.39 (9)° and the mol-ecule has an E conformation about the C=C bond. In the crystal, mol-ecules stack head-to-tail along the b-axis direction. They are linked by very weak C-H⋯O contacts, forming C(4) chains along [100]. Two chains are linked by a pair of very weak C-H⋯O contacts, enclosing inversion-dimeric R 2 (2)(8) ring motifs. There are also C-H⋯π inter-actions present, which link the double-stranded chains, forming a two-dimensional network.

Related literature

For general background to chalcones, see: Uchida et al. (1998 ▶); Indira et al. (2002 ▶); Treadwell (2006 ▶). For their various biological properties, see: Avila et al. (2008 ▶); ElSohly et al. (2001 ▶); Gafner et al. (1996 ▶); Akihisa et al. (2003 ▶); Szliszka et al. (2009 ▶); Xia et al. (2000 ▶); Lahtchev et al. (2008 ▶); Bandgar et al. (2010 ▶). For their enhanced cytotoxicity towards certain cancers, see: Won et al. (2005 ▶). For examples of chalcones with general formula Ar—CH–CH—CO—Ar, with mol­ecular pairing involving π–π inter­actions and hydrogen-bonding, see: Wang et al. (2005 ▶). For related halogen derivatives, see: Dutkiewicz et al. (2010 ▶); Qiu et al. (2006 ▶).

Experimental

Crystal data

C22H26O2

M = 322.43

Triclinic,

a = 5.6069 (9) Å

b = 7.7822 (13) Å

c = 22.864 (4) Å

α = 81.101 (5)°

β = 85.571 (5)°

γ = 69.879 (4)°

V = 925.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 200 K

0.50 × 0.26 × 0.16 mm

Data collection

Bruker X2S diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2005 ▶) T min = 0.965, T max = 0.989

5754 measured reflections

3149 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.09

3149 reflections

322 parameters

All H-atom parameters refined

Δρmax = 0.44 e Å−3

Δρmin = −0.24 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: JMol (Hanson, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813034429/zp2008sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034429/zp2008Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup4.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H26O2	Z = 2
Mr = 322.43	F(000) = 348
Triclinic, P1	Dx = 1.157 Mg m−3
a = 5.6069 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7822 (13) Å	Cell parameters from 2314 reflections
c = 22.864 (4) Å	θ = 0.9–25.1°
α = 81.101 (5)°	µ = 0.07 mm−1
β = 85.571 (5)°	T = 200 K
γ = 69.879 (4)°	Plate, yellow
V = 925.2 (3) Å3	0.50 × 0.26 × 0.16 mm

Bruker X2S diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
automatic scans	θmax = 25.1°, θmin = 0.9°
Absorption correction: multi-scan (SADABS, Bruker, 2005)	h = −6→6
Tmin = 0.965, Tmax = 0.989	k = −9→9
5754 measured reflections	l = −27→27

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)] = 0.051	All H-atom parameters refined
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0807P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3149 reflections	Δρmax = 0.44 e Å−3
322 parameters	Δρmin = −0.24 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: 0.055 (8)

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	0.0523 (3)	0.7906 (2)	0.72962 (7)	0.0430 (4)
C2	0.2373 (3)	0.7615 (2)	0.77569 (7)	0.0400 (4)
C3	0.1563 (3)	0.7911 (2)	0.83070 (7)	0.0387 (4)
C4	0.3023 (3)	0.7649 (2)	0.88344 (7)	0.0364 (4)
C5	0.1749 (3)	0.8252 (2)	0.93499 (7)	0.0413 (4)
C6	0.2981 (3)	0.8036 (2)	0.98702 (8)	0.0416 (4)
C7	0.5591 (3)	0.7171 (2)	0.98833 (7)	0.0351 (4)
C8	0.6904 (3)	0.6503 (2)	0.93778 (7)	0.0390 (4)
C9	0.5660 (3)	0.6753 (2)	0.88623 (7)	0.0382 (4)
C10	0.5762 (3)	0.7608 (2)	1.08943 (7)	0.0402 (4)
C11	0.7707 (3)	0.7139 (2)	1.13640 (7)	0.0417 (4)
C12	0.6526 (3)	0.7708 (2)	1.19529 (7)	0.0434 (5)
C13	0.8447 (4)	0.7246 (2)	1.24366 (8)	0.0449 (5)
C14	0.7285 (4)	0.7721 (2)	1.30362 (8)	0.0471 (5)
C15	0.9149 (4)	0.7081 (3)	1.35305 (9)	0.0608 (6)
C16	0.7959 (7)	0.7512 (4)	1.41297 (10)	0.0790 (7)
C17	0.3892 (4)	0.6901 (3)	0.64939 (8)	0.0485 (5)
C18	0.4548 (4)	0.6707 (3)	0.59057 (9)	0.0582 (5)
C19	0.2705 (4)	0.7373 (3)	0.54822 (9)	0.0596 (6)
C20	0.0207 (4)	0.8227 (3)	0.56481 (8)	0.0580 (6)
C21	−0.0447 (4)	0.8401 (3)	0.62334 (8)	0.0492 (5)
C22	0.1388 (3)	0.7733 (2)	0.66679 (7)	0.0403 (4)
O1	−0.1746 (2)	0.8262 (2)	0.74253 (5)	0.0659 (5)
O2	0.7021 (2)	0.68945 (15)	1.03686 (5)	0.0435 (3)
H2	0.421 (4)	0.718 (2)	0.7647 (7)	0.049 (5)*
H3	−0.021 (4)	0.828 (2)	0.8379 (7)	0.047 (5)*
H5	−0.003 (3)	0.881 (2)	0.9330 (7)	0.044 (5)*
H6	0.206 (3)	0.843 (2)	1.0227 (8)	0.051 (5)*
H8	0.867 (3)	0.587 (2)	0.9416 (7)	0.040 (4)*
H9	0.660 (3)	0.629 (2)	0.8518 (7)	0.043 (4)*
H10A	0.444 (3)	0.700 (2)	1.1034 (7)	0.053 (5)*
H10B	0.496 (3)	0.895 (2)	1.0810 (7)	0.044 (4)*
H11A	0.898 (3)	0.775 (2)	1.1222 (7)	0.049 (5)*
H11B	0.860 (3)	0.578 (2)	1.1418 (7)	0.042 (4)*
H12A	0.534 (4)	0.700 (2)	1.2111 (8)	0.059 (5)*
H12B	0.563 (3)	0.899 (3)	1.1912 (8)	0.052 (5)*
H13A	0.967 (4)	0.790 (2)	1.2316 (8)	0.058 (5)*
H13B	0.938 (4)	0.588 (3)	1.2473 (8)	0.059 (5)*
H14A	0.644 (3)	0.901 (3)	1.3017 (7)	0.051 (5)*
H14B	0.601 (4)	0.711 (3)	1.3149 (8)	0.064 (6)*
H15A	1.048 (4)	0.763 (3)	1.3422 (8)	0.070 (6)*
H15B	0.994 (4)	0.571 (3)	1.3551 (9)	0.076 (6)*
H16A	0.719 (4)	0.880 (3)	1.4161 (9)	0.078 (7)*
H16B	0.917 (5)	0.698 (4)	1.4446 (13)	0.119 (10)*
H16C	0.656 (5)	0.692 (4)	1.4224 (12)	0.121 (10)*
H17	0.517 (3)	0.644 (2)	0.6772 (8)	0.048 (5)*
H18	0.630 (4)	0.611 (2)	0.5772 (8)	0.064 (6)*
H19	0.319 (4)	0.725 (3)	0.5065 (9)	0.068 (6)*
H20	−0.115 (4)	0.867 (3)	0.5363 (9)	0.067 (6)*
H21	−0.219 (4)	0.898 (3)	0.6362 (8)	0.060 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0374 (11)	0.0448 (9)	0.0462 (10)	−0.0142 (8)	−0.0048 (8)	−0.0014 (7)
C2	0.0357 (11)	0.0423 (9)	0.0413 (10)	−0.0133 (8)	−0.0032 (8)	−0.0020 (7)
C3	0.0334 (10)	0.0376 (8)	0.0438 (10)	−0.0111 (7)	−0.0014 (8)	−0.0036 (7)
C4	0.0374 (10)	0.0317 (8)	0.0400 (9)	−0.0119 (7)	−0.0008 (7)	−0.0044 (7)
C5	0.0318 (10)	0.0410 (9)	0.0486 (11)	−0.0074 (8)	0.0003 (8)	−0.0111 (7)
C6	0.0393 (11)	0.0432 (9)	0.0406 (10)	−0.0095 (8)	0.0040 (8)	−0.0135 (7)
C7	0.0373 (10)	0.0312 (7)	0.0350 (9)	−0.0095 (7)	−0.0003 (7)	−0.0041 (6)
C8	0.0325 (10)	0.0401 (9)	0.0399 (9)	−0.0072 (8)	0.0010 (8)	−0.0046 (7)
C9	0.0366 (10)	0.0397 (8)	0.0351 (9)	−0.0094 (7)	0.0032 (8)	−0.0057 (7)
C10	0.0432 (11)	0.0379 (9)	0.0368 (9)	−0.0094 (8)	0.0036 (8)	−0.0091 (7)
C11	0.0459 (11)	0.0386 (9)	0.0380 (10)	−0.0109 (8)	−0.0013 (8)	−0.0052 (7)
C12	0.0455 (11)	0.0410 (9)	0.0403 (10)	−0.0096 (8)	−0.0023 (8)	−0.0066 (7)
C13	0.0493 (11)	0.0390 (9)	0.0425 (10)	−0.0088 (8)	−0.0060 (8)	−0.0059 (7)
C14	0.0545 (12)	0.0414 (10)	0.0426 (10)	−0.0120 (9)	−0.0046 (9)	−0.0055 (8)
C15	0.0751 (15)	0.0541 (12)	0.0495 (12)	−0.0130 (11)	−0.0172 (11)	−0.0088 (9)
C16	0.119 (2)	0.0727 (16)	0.0472 (13)	−0.0301 (16)	−0.0154 (14)	−0.0122 (11)
C17	0.0422 (12)	0.0569 (10)	0.0458 (11)	−0.0149 (9)	−0.0054 (9)	−0.0073 (8)
C18	0.0522 (13)	0.0721 (13)	0.0516 (12)	−0.0205 (10)	0.0036 (10)	−0.0159 (10)
C19	0.0697 (15)	0.0743 (13)	0.0412 (11)	−0.0317 (12)	0.0002 (10)	−0.0105 (10)
C20	0.0625 (15)	0.0695 (13)	0.0449 (12)	−0.0264 (11)	−0.0144 (10)	−0.0007 (9)
C21	0.0446 (12)	0.0557 (11)	0.0475 (11)	−0.0181 (9)	−0.0078 (9)	−0.0022 (8)
C22	0.0438 (11)	0.0398 (9)	0.0404 (9)	−0.0186 (8)	−0.0052 (8)	−0.0028 (7)
O1	0.0394 (9)	0.1036 (11)	0.0515 (8)	−0.0195 (7)	−0.0026 (6)	−0.0110 (7)
O2	0.0394 (7)	0.0494 (7)	0.0347 (7)	−0.0047 (5)	−0.0026 (5)	−0.0088 (5)

C1—O1	1.228 (2)	C12—H12A	1.014 (18)
C1—C2	1.473 (2)	C12—H12B	0.940 (18)
C1—C22	1.491 (2)	C13—C14	1.515 (2)
C2—C3	1.331 (2)	C13—H13A	0.986 (18)
C2—H2	0.991 (19)	C13—H13B	1.005 (19)
C3—C4	1.459 (2)	C14—C15	1.506 (3)
C3—H3	0.944 (18)	C14—H14A	0.947 (19)
C4—C5	1.389 (2)	C14—H14B	0.99 (2)
C4—C9	1.403 (2)	C15—C16	1.510 (3)
C5—C6	1.380 (2)	C15—H15A	0.98 (2)
C5—H5	0.944 (18)	C15—H15B	1.00 (2)
C6—C7	1.385 (2)	C16—H16A	0.95 (2)
C6—H6	0.963 (18)	C16—H16B	0.97 (3)
C7—O2	1.3659 (19)	C16—H16C	1.03 (3)
C7—C8	1.393 (2)	C17—C18	1.384 (3)
C8—C9	1.370 (2)	C17—C22	1.385 (3)
C8—H8	0.945 (18)	C17—H17	0.934 (18)
C9—H9	0.959 (17)	C18—C19	1.380 (3)
C10—O2	1.4343 (19)	C18—H18	0.98 (2)
C10—C11	1.504 (2)	C19—C20	1.379 (3)
C10—H10A	1.019 (17)	C19—H19	0.982 (19)
C10—H10B	0.977 (17)	C20—C21	1.375 (3)
C11—C12	1.514 (2)	C20—H20	0.97 (2)
C11—H11A	0.992 (17)	C21—C22	1.395 (2)
C11—H11B	0.995 (17)	C21—H21	0.966 (19)
C12—C13	1.519 (2)
O1—C1—C2	120.52 (15)	H12A—C12—H12B	110.1 (16)
O1—C1—C22	119.01 (15)	C14—C13—C12	114.23 (15)
C2—C1—C22	120.45 (15)	C14—C13—H13A	108.9 (10)
C3—C2—C1	119.86 (16)	C12—C13—H13A	109.1 (11)
C3—C2—H2	121.6 (10)	C14—C13—H13B	108.6 (10)
C1—C2—H2	118.5 (10)	C12—C13—H13B	107.0 (10)
C2—C3—C4	129.51 (17)	H13A—C13—H13B	108.9 (15)
C2—C3—H3	116.6 (10)	C15—C14—C13	114.37 (17)
C4—C3—H3	113.8 (10)	C15—C14—H14A	109.2 (10)
C5—C4—C9	117.15 (15)	C13—C14—H14A	110.3 (10)
C5—C4—C3	118.98 (15)	C15—C14—H14B	106.2 (11)
C9—C4—C3	123.82 (15)	C13—C14—H14B	108.9 (10)
C6—C5—C4	122.69 (17)	H14A—C14—H14B	107.6 (16)
C6—C5—H5	120.8 (10)	C14—C15—C16	114.0 (2)
C4—C5—H5	116.5 (10)	C14—C15—H15A	107.9 (12)
C5—C6—C7	118.98 (16)	C16—C15—H15A	111.3 (12)
C5—C6—H6	121.5 (11)	C14—C15—H15B	107.1 (12)
C7—C6—H6	119.5 (11)	C16—C15—H15B	108.3 (11)
O2—C7—C6	124.38 (14)	H15A—C15—H15B	108.1 (18)
O2—C7—C8	116.11 (14)	C15—C16—H16A	114.9 (13)
C6—C7—C8	119.51 (15)	C15—C16—H16B	112.3 (17)
C9—C8—C7	120.79 (16)	H16A—C16—H16B	107 (2)
C9—C8—H8	123.0 (9)	C15—C16—H16C	108.7 (15)
C7—C8—H8	116.2 (9)	H16A—C16—H16C	107 (2)
C8—C9—C4	120.84 (16)	H16B—C16—H16C	106 (2)
C8—C9—H9	119.5 (10)	C18—C17—C22	120.81 (18)
C4—C9—H9	119.7 (10)	C18—C17—H17	118.4 (11)
O2—C10—C11	108.43 (13)	C22—C17—H17	120.8 (11)
O2—C10—H10A	108.8 (9)	C19—C18—C17	120.1 (2)
C11—C10—H10A	109.4 (10)	C19—C18—H18	117.5 (11)
O2—C10—H10B	109.6 (9)	C17—C18—H18	122.4 (11)
C11—C10—H10B	109.8 (10)	C20—C19—C18	119.71 (19)
H10A—C10—H10B	110.8 (14)	C20—C19—H19	120.7 (12)
C10—C11—C12	112.39 (14)	C18—C19—H19	119.6 (12)
C10—C11—H11A	108.4 (10)	C21—C20—C19	120.16 (19)
C12—C11—H11A	110.8 (9)	C21—C20—H20	118.0 (12)
C10—C11—H11B	108.5 (9)	C19—C20—H20	121.8 (12)
C12—C11—H11B	108.7 (9)	C20—C21—C22	120.95 (19)
H11A—C11—H11B	107.9 (14)	C20—C21—H21	121.8 (11)
C11—C12—C13	113.55 (15)	C22—C21—H21	117.3 (11)
C11—C12—H12A	110.2 (10)	C17—C22—C21	118.26 (16)
C13—C12—H12A	104.3 (10)	C17—C22—C1	123.77 (15)
C11—C12—H12B	110.4 (11)	C21—C22—C1	117.95 (15)
C13—C12—H12B	108.2 (11)	C7—O2—C10	118.10 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.99 (2)	2.67 (2)	3.513 (2)	143.3 (12)
C8—H8···O2ii	0.95 (2)	2.64 (2)	3.545 (2)	159.3 (13)
C10—H10B···Cg1iii	0.98 (2)	2.972 (15)	3.8279 (18)	146.6 (13)
C16—H16A···Cg2iii	0.97 (3)	2.97 (2)	3.792 (3)	144.5 (18)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C4–C9 and C17–C22, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.99 (2)	2.67 (2)	3.513 (2)	143.3 (12)
C8—H8⋯O2ii	0.95 (2)	2.64 (2)	3.545 (2)	159.3 (13)
C10—H10B⋯Cg1iii	0.98 (2)	2.972 (15)	3.8279 (18)	146.6 (13)
C16—H16A⋯Cg2iii	0.97 (3)	2.97 (2)	3.792 (3)	144.5 (18)

Symmetry codes: (i) ; (ii) ; (iii) .