Crystal structure of (E)-1,3-bis-(6-methoxy-naphthalen-2-yl)prop-2-en-1-one.

In the title compound, C25H20O3, the central -C(=O)-C=C- chain is disordered over two positions about the central C atom, with an occupancy ratio of 0.848 (6):0.152 (6). The mol-ecule is twisted with the two naphthalene ring systems being inclined to one another by 52.91 (9)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a three-dimensional structure. The structure was refined as a two-component twin with a 180 ° rotation about the c* axis.

Related literature

For natural sources of chalcones and their derivatives, see: Anderson & Markham (2006 ▸); Yadav et al. (2011 ▸). For examples of their biological activities, see: Liu et al. (2011 ▸); Siddiqui et al. (2012 ▸). For their use as synthons for the preparation of five- and six-membered ring systems, see: Powers et al. (1998 ▸). For their use as inter­mediates in the synthesis of pharmaceutical mol­ecules, see: Perozo-Rondon et al. (2006 ▸). For the crystal structure of a closely related compound, 3-(6-meth­oxy-2-naphth­yl)-1-(2-naphth­yl)prop-2-en-1-one, see: Yathirajan et al. (2006 ▸).

Experimental

Crystal data

C25H20O3

M = 368.41

Monoclinic

a = 6.027 (5) Å

b = 19.926 (5) Å

c = 15.415 (5) Å

β = 90.366 (5)°

V = 1851.2 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS: Bruker, 2004 ▸) T min = 0.932, T max = 0.951

3345 measured reflections

3345 independent reflections

1837 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.179

S = 1.13

3345 reflections

267 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015019714/su5219sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019714/su5219Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019714/su5219Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019714/su5219fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered O atom is shown.

Click here for additional data file.

c . DOI: 10.1107/S2056989015019714/su5219fig2.tif

A view along the c axis of the crystal packing of the title compound.

CCDC reference: 1432044

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

C25H20O3	F(000) = 776
Mr = 368.41	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.027 (5) Å	Cell parameters from 4691 reflections
b = 19.926 (5) Å	θ = 2.6–22.4°
c = 15.415 (5) Å	µ = 0.09 mm−1
β = 90.366 (5)°	T = 293 K
V = 1851.2 (17) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	1837 reflections with I > 2σ(I)
Radiation source: Sealed tube	Rint = 0.072
ω and φ scan	θmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS: Bruker, 2004)	h = −7→7
Tmin = 0.932, Tmax = 0.951	k = −23→23
3345 measured reflections	l = 0→18
3345 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061	w = 1/[σ2(Fo2) + (0.076P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.179	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.19 e Å−3
3345 reflections	Δρmin = −0.16 e Å−3
267 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.0042 (12)

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.7149 (4)	0.07041 (12)	0.81151 (15)	0.0752 (7)
O2A	0.3022 (4)	0.46629 (14)	0.8854 (2)	0.0831 (12)	0.848 (6)
O2B	0.3818 (18)	0.5689 (8)	0.9159 (10)	0.075 (6)	0.152 (6)
O3	1.0538 (4)	0.94015 (12)	0.91441 (16)	0.0810 (8)
C1	0.9200 (6)	0.05490 (18)	0.7708 (3)	0.0878 (12)
H1A	0.9265	0.0769	0.7155	0.132*
H1B	0.9311	0.0072	0.7628	0.132*
H1C	1.0405	0.0701	0.8068	0.132*
C2	0.6696 (5)	0.13625 (18)	0.82763 (19)	0.0588 (9)
C3	0.4657 (5)	0.14718 (18)	0.8680 (2)	0.0637 (9)
H3	0.3764	0.1108	0.8821	0.076*
C4	0.3971 (5)	0.20984 (18)	0.88679 (19)	0.0624 (9)
H4	0.2601	0.2161	0.9130	0.075*
C5	0.5308 (4)	0.26629 (16)	0.86723 (18)	0.0507 (8)
C6	0.4623 (5)	0.33174 (17)	0.88371 (18)	0.0582 (9)
H6	0.3225	0.3389	0.9071	0.070*
C7	0.5958 (5)	0.38617 (16)	0.86635 (19)	0.0568 (8)
C8	0.8060 (5)	0.37394 (18)	0.8290 (2)	0.0631 (9)
H8	0.9001	0.4098	0.8174	0.076*
C9	0.8711 (5)	0.31106 (18)	0.8100 (2)	0.0619 (9)
H9	1.0084	0.3045	0.7842	0.074*
C10	0.7380 (4)	0.25513 (16)	0.82814 (18)	0.0513 (8)
C11	0.8029 (5)	0.18913 (17)	0.80906 (19)	0.0576 (8)
H11	0.9397	0.1815	0.7833	0.069*
C12	0.5122 (6)	0.45453 (18)	0.8827 (2)	0.0683 (10)
H12B	0.3602	0.4619	0.8864	0.082*	0.152 (6)
C13	0.6636 (5)	0.51023 (18)	0.8930 (2)	0.0664 (9)
H13A	0.8128	0.5016	0.9039	0.080*
C14	0.5946 (5)	0.57381 (18)	0.8872 (2)	0.0660 (9)
H14A	0.4446	0.5796	0.8747	0.079*	0.848 (6)
C15	0.7225 (5)	0.63517 (17)	0.89786 (19)	0.0548 (8)
C16	0.6339 (5)	0.69511 (17)	0.87011 (19)	0.0575 (9)
H16	0.4948	0.6948	0.8436	0.069*
C17	0.7436 (4)	0.75620 (16)	0.87992 (18)	0.0514 (8)
C18	0.6536 (5)	0.81769 (19)	0.8512 (2)	0.0628 (9)
H18	0.5163	0.8177	0.8234	0.075*
C19	0.7603 (5)	0.87635 (18)	0.8629 (2)	0.0656 (9)
H19	0.6986	0.9161	0.8423	0.079*
C20	0.9658 (5)	0.87709 (17)	0.9066 (2)	0.0613 (9)
C21	1.0620 (5)	0.81927 (16)	0.93433 (18)	0.0534 (8)
H21	1.1999	0.8206	0.9617	0.064*
C22	0.9538 (4)	0.75732 (16)	0.92185 (17)	0.0491 (7)
C23	1.0433 (5)	0.69571 (16)	0.94924 (19)	0.0536 (8)
H23	1.1821	0.6953	0.9759	0.064*
C24	0.9338 (5)	0.63677 (16)	0.93804 (19)	0.0573 (8)
H24	0.9986	0.5970	0.9570	0.069*
C25	1.2506 (6)	0.94859 (18)	0.9618 (3)	0.0897 (12)
H25A	1.2274	0.9351	1.0209	0.135*
H25B	1.2941	0.9949	0.9603	0.135*
H25C	1.3654	0.9215	0.9368	0.135*

	U11	U22	U33	U12	U13	U23
O1	0.0769 (16)	0.0723 (18)	0.0765 (16)	−0.0081 (12)	0.0102 (13)	0.0067 (13)
O2A	0.0531 (19)	0.084 (2)	0.112 (2)	−0.0078 (14)	0.0012 (15)	0.0059 (17)
O2B	0.039 (9)	0.096 (13)	0.091 (12)	0.008 (7)	−0.008 (7)	−0.015 (9)
O3	0.0854 (17)	0.0663 (17)	0.0910 (18)	−0.0005 (13)	−0.0171 (14)	0.0050 (13)
C1	0.081 (3)	0.089 (3)	0.093 (3)	0.006 (2)	0.014 (2)	0.006 (2)
C2	0.055 (2)	0.071 (2)	0.0501 (19)	−0.0080 (17)	−0.0043 (15)	0.0090 (17)
C3	0.057 (2)	0.073 (3)	0.061 (2)	−0.0186 (18)	0.0040 (16)	0.0117 (19)
C4	0.0439 (17)	0.092 (3)	0.052 (2)	−0.0166 (18)	0.0061 (14)	0.0073 (19)
C5	0.0416 (16)	0.071 (2)	0.0393 (16)	−0.0106 (15)	−0.0027 (13)	0.0049 (16)
C6	0.0461 (18)	0.088 (3)	0.0403 (17)	−0.0165 (17)	−0.0003 (13)	−0.0003 (17)
C7	0.0517 (19)	0.069 (2)	0.0495 (19)	−0.0129 (16)	−0.0015 (14)	−0.0002 (16)
C8	0.056 (2)	0.072 (3)	0.061 (2)	−0.0228 (17)	0.0017 (16)	0.0061 (18)
C9	0.0464 (18)	0.084 (3)	0.056 (2)	−0.0174 (17)	0.0040 (15)	0.0064 (19)
C10	0.0419 (16)	0.072 (2)	0.0400 (16)	−0.0126 (16)	−0.0033 (13)	0.0063 (16)
C11	0.0439 (17)	0.079 (2)	0.0501 (19)	−0.0083 (17)	0.0025 (14)	0.0114 (17)
C12	0.070 (2)	0.082 (3)	0.053 (2)	−0.021 (2)	0.0053 (17)	0.0013 (18)
C13	0.058 (2)	0.075 (3)	0.066 (2)	−0.0085 (19)	−0.0023 (16)	0.0023 (19)
C14	0.0477 (19)	0.082 (3)	0.069 (2)	−0.0019 (18)	−0.0021 (16)	−0.014 (2)
C15	0.0490 (18)	0.068 (2)	0.0475 (18)	0.0004 (16)	−0.0006 (14)	−0.0124 (16)
C16	0.0439 (17)	0.077 (3)	0.0512 (19)	0.0023 (16)	−0.0057 (14)	−0.0156 (17)
C17	0.0464 (17)	0.065 (2)	0.0428 (17)	0.0082 (16)	−0.0002 (14)	−0.0077 (15)
C18	0.0486 (18)	0.086 (3)	0.053 (2)	0.0098 (18)	−0.0033 (15)	−0.0082 (19)
C19	0.063 (2)	0.071 (3)	0.063 (2)	0.0156 (18)	−0.0007 (17)	0.0020 (18)
C20	0.063 (2)	0.064 (2)	0.057 (2)	0.0004 (18)	0.0026 (16)	−0.0042 (17)
C21	0.0472 (17)	0.066 (2)	0.0469 (18)	0.0018 (16)	−0.0007 (14)	0.0005 (16)
C22	0.0457 (16)	0.063 (2)	0.0389 (16)	0.0029 (15)	0.0028 (13)	−0.0048 (15)
C23	0.0441 (17)	0.070 (2)	0.0469 (18)	0.0016 (16)	−0.0069 (13)	−0.0036 (16)
C24	0.0536 (19)	0.066 (2)	0.0521 (19)	0.0056 (16)	−0.0011 (15)	−0.0022 (16)
C25	0.081 (3)	0.076 (3)	0.112 (3)	−0.006 (2)	−0.013 (2)	0.000 (2)

O1—C2	1.363 (4)	C12—C13	1.445 (4)
O1—C1	1.423 (4)	C12—H12B	0.9300
O2A—C12	1.288 (4)	C13—C14	1.336 (4)
O2B—C14	1.363 (11)	C13—H13A	0.9300
O3—C20	1.369 (4)	C14—C15	1.454 (4)
O3—C25	1.400 (4)	C14—H14A	0.9300
C1—H1A	0.9600	C15—C16	1.375 (4)
C1—H1B	0.9600	C15—C24	1.413 (4)
C1—H1C	0.9600	C16—C17	1.393 (4)
C2—C11	1.357 (4)	C16—H16	0.9300
C2—C3	1.398 (4)	C17—C18	1.410 (4)
C3—C4	1.347 (4)	C17—C22	1.419 (4)
C3—H3	0.9300	C18—C19	1.346 (4)
C4—C5	1.417 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.406 (5)
C5—C6	1.392 (4)	C19—H19	0.9300
C5—C10	1.408 (4)	C20—C21	1.358 (4)
C6—C7	1.377 (4)	C21—C22	1.409 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.416 (4)	C22—C23	1.405 (4)
C7—C12	1.475 (4)	C23—C24	1.358 (4)
C8—C9	1.346 (4)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.402 (4)	C25—H25A	0.9600
C9—H9	0.9300	C25—H25B	0.9600
C10—C11	1.404 (4)	C25—H25C	0.9600
C11—H11	0.9300
C2—O1—C1	117.7 (3)	C14—C13—H13A	119.2
C20—O3—C25	118.9 (3)	C12—C13—H13A	119.2
O1—C1—H1A	109.5	C13—C14—O2B	101.7 (7)
O1—C1—H1B	109.5	C13—C14—C15	128.7 (3)
H1A—C1—H1B	109.5	O2B—C14—C15	121.5 (7)
O1—C1—H1C	109.5	C13—C14—H14A	115.6
H1A—C1—H1C	109.5	C15—C14—H14A	115.6
H1B—C1—H1C	109.5	C16—C15—C24	117.6 (3)
C11—C2—O1	126.1 (3)	C16—C15—C14	119.4 (3)
C11—C2—C3	119.8 (3)	C24—C15—C14	123.0 (3)
O1—C2—C3	114.1 (3)	C15—C16—C17	122.8 (3)
C4—C3—C2	120.8 (3)	C15—C16—H16	118.6
C4—C3—H3	119.6	C17—C16—H16	118.6
C2—C3—H3	119.6	C16—C17—C18	123.0 (3)
C3—C4—C5	120.9 (3)	C16—C17—C22	119.0 (3)
C3—C4—H4	119.5	C18—C17—C22	118.0 (3)
C5—C4—H4	119.5	C19—C18—C17	122.0 (3)
C6—C5—C10	119.4 (3)	C19—C18—H18	119.0
C6—C5—C4	122.4 (3)	C17—C18—H18	119.0
C10—C5—C4	118.2 (3)	C18—C19—C20	119.5 (3)
C7—C6—C5	121.9 (3)	C18—C19—H19	120.3
C7—C6—H6	119.1	C20—C19—H19	120.3
C5—C6—H6	119.1	C21—C20—O3	125.9 (3)
C6—C7—C8	117.9 (3)	C21—C20—C19	121.0 (3)
C6—C7—C12	119.6 (3)	O3—C20—C19	113.1 (3)
C8—C7—C12	122.4 (3)	C20—C21—C22	120.3 (3)
C9—C8—C7	120.8 (3)	C20—C21—H21	119.9
C9—C8—H8	119.6	C22—C21—H21	119.9
C7—C8—H8	119.6	C23—C22—C21	123.2 (3)
C8—C9—C10	121.9 (3)	C23—C22—C17	117.6 (3)
C8—C9—H9	119.0	C21—C22—C17	119.2 (3)
C10—C9—H9	119.0	C24—C23—C22	122.2 (3)
C9—C10—C11	122.8 (3)	C24—C23—H23	118.9
C9—C10—C5	118.0 (3)	C22—C23—H23	118.9
C11—C10—C5	119.1 (3)	C23—C24—C15	120.7 (3)
C2—C11—C10	121.1 (3)	C23—C24—H24	119.6
C2—C11—H11	119.4	C15—C24—H24	119.6
C10—C11—H11	119.4	O3—C25—H25A	109.5
O2A—C12—C13	118.5 (3)	O3—C25—H25B	109.5
O2A—C12—C7	120.7 (3)	H25A—C25—H25B	109.5
C13—C12—C7	120.8 (3)	O3—C25—H25C	109.5
C13—C12—H12B	119.6	H25A—C25—H25C	109.5
C7—C12—H12B	119.6	H25B—C25—H25C	109.5
C14—C13—C12	121.7 (3)
C1—O1—C2—C11	−0.5 (5)	C12—C13—C14—O2B	30.1 (7)
C1—O1—C2—C3	−179.7 (3)	C12—C13—C14—C15	178.3 (3)
C11—C2—C3—C4	1.7 (5)	C13—C14—C15—C16	165.1 (3)
O1—C2—C3—C4	−179.0 (3)	O2B—C14—C15—C16	−52.0 (9)
C2—C3—C4—C5	−0.9 (5)	C13—C14—C15—C24	−16.7 (5)
C3—C4—C5—C6	178.3 (3)	O2B—C14—C15—C24	126.2 (8)
C3—C4—C5—C10	−0.4 (4)	C24—C15—C16—C17	0.1 (4)
C10—C5—C6—C7	−2.9 (4)	C14—C15—C16—C17	178.4 (3)
C4—C5—C6—C7	178.4 (3)	C15—C16—C17—C18	179.7 (3)
C5—C6—C7—C8	1.4 (4)	C15—C16—C17—C22	−1.3 (4)
C5—C6—C7—C12	178.2 (3)	C16—C17—C18—C19	178.6 (3)
C6—C7—C8—C9	0.9 (5)	C22—C17—C18—C19	−0.3 (4)
C12—C7—C8—C9	−175.8 (3)	C17—C18—C19—C20	−1.3 (5)
C7—C8—C9—C10	−1.6 (5)	C25—O3—C20—C21	−6.3 (5)
C8—C9—C10—C11	−179.9 (3)	C25—O3—C20—C19	175.6 (3)
C8—C9—C10—C5	0.0 (4)	C18—C19—C20—C21	2.4 (5)
C6—C5—C10—C9	2.2 (4)	C18—C19—C20—O3	−179.4 (3)
C4—C5—C10—C9	−179.1 (3)	O3—C20—C21—C22	−179.7 (3)
C6—C5—C10—C11	−177.9 (3)	C19—C20—C21—C22	−1.8 (5)
C4—C5—C10—C11	0.8 (4)	C20—C21—C22—C23	−179.7 (3)
O1—C2—C11—C10	179.5 (3)	C20—C21—C22—C17	0.1 (4)
C3—C2—C11—C10	−1.3 (4)	C16—C17—C22—C23	1.8 (4)
C9—C10—C11—C2	179.9 (3)	C18—C17—C22—C23	−179.2 (3)
C5—C10—C11—C2	0.0 (4)	C16—C17—C22—C21	−178.0 (3)
C6—C7—C12—O2A	−22.7 (5)	C18—C17—C22—C21	1.0 (4)
C8—C7—C12—O2A	154.0 (3)	C21—C22—C23—C24	178.7 (3)
C6—C7—C12—C13	159.5 (3)	C17—C22—C23—C24	−1.2 (4)
C8—C7—C12—C13	−23.8 (5)	C22—C23—C24—C15	0.0 (4)
O2A—C12—C13—C14	−14.0 (5)	C16—C15—C24—C23	0.6 (4)
C7—C12—C13—C14	163.8 (3)	C14—C15—C24—C23	−177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg4i	0.93	2.86	3.543 (4)	131
C18—H18···Cg2ii	0.93	2.85	3.611 (4)	140
C23—H23···Cg2iii	0.93	2.88	3.592 (4)	134

Table 1

Hydrogen-bond geometry (, )

Cg2 and Cg4 are the centroids of rings C5-C10 and C17-C22, respectively.

DHA	DH	HA	D A	DHA
C9H9Cg4i	0.93	2.86	3.543(4)	131
C18H18Cg2ii	0.93	2.85	3.611(4)	140
C23H23Cg2iii	0.93	2.88	3.592(4)	134

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