(2E)-3-[4-(Benz-yloxy)phen-yl]-1-(pyridin-3-yl)prop-2-en-1-one.

The title compound, C(21)H(17)NO(2), exists in an E conformation with respect to the C=C bond. The pyridine ring forms dihedral angles of 5.57 (7) and 82.30 (9)°, respectively, with the central benzene ring and the terminal phenyl ring. The dihedral angle between the benzene and phenyl rings is 87.69 (8)°. No significant inter-molecular inter-actions are observed.

Related literature

For the pharmacological activity of chalcones, see: Matsuda et al. (2003 ▶); Lopez et al. (2001 ▶); Agarwal et al. (2005 ▶). For related structures, see: Bibila Mayaya Bisseyou et al. (2007 ▶); Liu et al. (2005 ▶); Jasinski et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H17NO2

M = 315.36

Monoclinic,

a = 5.9845 (6) Å

b = 38.187 (4) Å

c = 8.5412 (7) Å

β = 123.372 (5)°

V = 1630.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.40 × 0.33 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.986

18812 measured reflections

4751 independent reflections

3171 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.02

4751 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034897/is5181sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034897/is5181Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034897/is5181Isup3.cml

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

C21H17NO2	F(000) = 664
Mr = 315.36	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4372 reflections
a = 5.9845 (6) Å	θ = 2.9–26.5°
b = 38.187 (4) Å	µ = 0.08 mm−1
c = 8.5412 (7) Å	T = 100 K
β = 123.372 (5)°	Block, yellow
V = 1630.1 (3) Å3	0.40 × 0.33 × 0.17 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	4751 independent reflections
Radiation source: fine-focus sealed tube	3171 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.968, Tmax = 0.986	k = −53→47
18812 measured reflections	l = −11→11

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.059P)2 + 0.2532P] where P = (Fo2 + 2Fc2)/3
4751 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.1642 (2)	−0.12817 (2)	0.76557 (15)	0.0534 (3)
O2	0.6625 (3)	0.04322 (3)	0.69065 (19)	0.0690 (3)
N1	0.5921 (3)	0.14650 (3)	0.7813 (2)	0.0668 (4)
C1	−0.2000 (4)	−0.20724 (4)	0.8950 (3)	0.0637 (4)
H1A	−0.0178	−0.2048	0.9949	0.076*
C2	−0.3631 (4)	−0.23073 (4)	0.9115 (3)	0.0725 (5)
H2A	−0.2924	−0.2442	1.0225	0.087*
C3	−0.6271 (4)	−0.23442 (4)	0.7671 (3)	0.0700 (5)
H3A	−0.7382	−0.2506	0.7778	0.084*
C4	−0.7299 (4)	−0.21464 (4)	0.6074 (3)	0.0673 (4)
H4A	−0.9128	−0.2169	0.5085	0.081*
C5	−0.5668 (3)	−0.19132 (4)	0.5905 (2)	0.0583 (4)
H5A	−0.6381	−0.1779	0.4792	0.070*
C6	−0.3010 (3)	−0.18749 (3)	0.7344 (2)	0.0496 (3)
C7	−0.1254 (3)	−0.16226 (3)	0.7147 (2)	0.0524 (3)
H7A	0.0645	−0.1693	0.7978	0.063*
H7B	−0.1734	−0.1621	0.5838	0.063*
C8	−0.0323 (3)	−0.10096 (3)	0.74586 (18)	0.0425 (3)
C9	−0.0638 (3)	−0.06836 (3)	0.8049 (2)	0.0480 (3)
H9A	−0.1686	−0.0664	0.8569	0.058*
C10	0.0551 (3)	−0.03911 (3)	0.7886 (2)	0.0467 (3)
H10A	0.0300	−0.0170	0.8282	0.056*
C11	0.2133 (2)	−0.04140 (3)	0.71422 (18)	0.0427 (3)
C12	0.2424 (3)	−0.07406 (3)	0.65656 (19)	0.0485 (3)
H12A	0.3472	−0.0761	0.6045	0.058*
C13	0.1238 (3)	−0.10387 (4)	0.6723 (2)	0.0484 (3)
H13A	0.1490	−0.1260	0.6332	0.058*
C14	0.3499 (3)	−0.01114 (3)	0.69900 (19)	0.0467 (3)
H14A	0.4507	−0.0153	0.6454	0.056*
C15	0.3490 (3)	0.02140 (4)	0.7514 (2)	0.0507 (3)
H15A	0.2462	0.0269	0.8021	0.061*
C16	0.5021 (3)	0.04934 (4)	0.73355 (19)	0.0470 (3)
C17	0.4655 (3)	0.08627 (3)	0.77386 (18)	0.0433 (3)
C18	0.6038 (3)	0.11266 (4)	0.7499 (2)	0.0562 (4)
H18A	0.7154	0.1060	0.7079	0.067*
C19	0.4329 (4)	0.15510 (4)	0.8397 (2)	0.0652 (4)
H19A	0.4199	0.1791	0.8629	0.078*
C20	0.2878 (4)	0.13133 (4)	0.8679 (3)	0.0687 (5)
H20A	0.1783	0.1388	0.9103	0.082*
C21	0.3026 (3)	0.09635 (4)	0.8339 (2)	0.0579 (4)
H21A	0.2022	0.0794	0.8516	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0640 (6)	0.0392 (5)	0.0748 (7)	−0.0061 (4)	0.0494 (6)	−0.0041 (4)
O2	0.0864 (8)	0.0557 (6)	0.1028 (9)	−0.0082 (5)	0.0761 (8)	−0.0071 (6)
N1	0.0781 (10)	0.0477 (7)	0.0865 (10)	−0.0058 (6)	0.0528 (9)	0.0013 (6)
C1	0.0684 (10)	0.0500 (8)	0.0743 (10)	0.0020 (7)	0.0402 (9)	0.0058 (7)
C2	0.0935 (14)	0.0524 (9)	0.0850 (12)	0.0029 (9)	0.0576 (12)	0.0134 (8)
C3	0.0904 (13)	0.0484 (8)	0.0985 (13)	−0.0127 (8)	0.0693 (12)	−0.0046 (8)
C4	0.0667 (10)	0.0617 (9)	0.0824 (12)	−0.0148 (8)	0.0466 (9)	−0.0097 (8)
C5	0.0647 (10)	0.0507 (8)	0.0662 (9)	−0.0047 (7)	0.0403 (8)	−0.0012 (7)
C6	0.0615 (9)	0.0347 (6)	0.0651 (9)	−0.0013 (6)	0.0427 (8)	−0.0047 (6)
C7	0.0595 (9)	0.0414 (7)	0.0660 (9)	−0.0045 (6)	0.0407 (8)	−0.0062 (6)
C8	0.0407 (7)	0.0410 (6)	0.0458 (7)	−0.0022 (5)	0.0237 (6)	0.0015 (5)
C9	0.0504 (8)	0.0456 (7)	0.0593 (8)	0.0005 (6)	0.0372 (7)	0.0008 (6)
C10	0.0479 (7)	0.0395 (6)	0.0576 (8)	0.0009 (5)	0.0321 (7)	0.0009 (5)
C11	0.0384 (6)	0.0453 (7)	0.0424 (6)	−0.0012 (5)	0.0209 (6)	0.0035 (5)
C12	0.0489 (8)	0.0525 (7)	0.0535 (8)	−0.0048 (6)	0.0342 (7)	−0.0043 (6)
C13	0.0510 (8)	0.0446 (7)	0.0555 (8)	−0.0037 (6)	0.0330 (7)	−0.0067 (6)
C14	0.0465 (7)	0.0492 (7)	0.0482 (7)	−0.0024 (6)	0.0284 (6)	0.0036 (6)
C15	0.0560 (8)	0.0477 (7)	0.0596 (8)	−0.0048 (6)	0.0390 (7)	0.0015 (6)
C16	0.0510 (8)	0.0485 (7)	0.0486 (7)	−0.0030 (6)	0.0320 (6)	0.0021 (6)
C17	0.0433 (7)	0.0467 (7)	0.0409 (6)	−0.0022 (5)	0.0238 (6)	0.0033 (5)
C18	0.0607 (9)	0.0508 (8)	0.0707 (10)	−0.0041 (6)	0.0447 (8)	0.0024 (7)
C19	0.0721 (11)	0.0509 (8)	0.0724 (11)	−0.0003 (7)	0.0397 (9)	−0.0062 (7)
C20	0.0771 (11)	0.0644 (10)	0.0856 (12)	−0.0041 (8)	0.0582 (10)	−0.0135 (8)
C21	0.0640 (9)	0.0580 (8)	0.0682 (9)	−0.0079 (7)	0.0469 (8)	−0.0041 (7)

O1—C8	1.3700 (15)	C9—H9A	0.9500
O1—C7	1.4313 (15)	C10—C11	1.4037 (18)
O2—C16	1.2235 (16)	C10—H10A	0.9500
N1—C18	1.3297 (19)	C11—C12	1.3869 (18)
N1—C19	1.337 (2)	C11—C14	1.4620 (17)
C1—C6	1.380 (2)	C12—C13	1.3866 (18)
C1—C2	1.388 (2)	C12—H12A	0.9500
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.376 (3)	C14—C15	1.3217 (19)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.373 (3)	C15—C16	1.4682 (18)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.386 (2)	C16—C17	1.4963 (18)
C4—H4A	0.9500	C17—C21	1.3826 (19)
C5—C6	1.383 (2)	C17—C18	1.3889 (18)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.5019 (18)	C19—C20	1.366 (2)
C7—H7A	0.9900	C19—H19A	0.9500
C7—H7B	0.9900	C20—C21	1.380 (2)
C8—C13	1.3877 (18)	C20—H20A	0.9500
C8—C9	1.3943 (18)	C21—H21A	0.9500
C9—C10	1.3718 (18)
C8—O1—C7	116.85 (10)	C11—C10—H10A	119.6
C18—N1—C19	116.22 (13)	C12—C11—C10	117.68 (11)
C6—C1—C2	120.41 (17)	C12—C11—C14	119.58 (12)
C6—C1—H1A	119.8	C10—C11—C14	122.73 (12)
C2—C1—H1A	119.8	C13—C12—C11	122.20 (12)
C3—C2—C1	119.97 (16)	C13—C12—H12A	118.9
C3—C2—H2A	120.0	C11—C12—H12A	118.9
C1—C2—H2A	120.0	C12—C13—C8	119.10 (12)
C4—C3—C2	120.02 (15)	C12—C13—H13A	120.4
C4—C3—H3A	120.0	C8—C13—H13A	120.4
C2—C3—H3A	120.0	C15—C14—C11	127.31 (12)
C3—C4—C5	120.03 (17)	C15—C14—H14A	116.3
C3—C4—H4A	120.0	C11—C14—H14A	116.3
C5—C4—H4A	120.0	C14—C15—C16	121.93 (13)
C6—C5—C4	120.44 (16)	C14—C15—H15A	119.0
C6—C5—H5A	119.8	C16—C15—H15A	119.0
C4—C5—H5A	119.8	O2—C16—C15	121.97 (13)
C1—C6—C5	119.13 (14)	O2—C16—C17	119.18 (12)
C1—C6—C7	120.75 (14)	C15—C16—C17	118.83 (11)
C5—C6—C7	120.12 (13)	C21—C17—C18	116.88 (13)
O1—C7—C6	108.00 (11)	C21—C17—C16	124.77 (12)
O1—C7—H7A	110.1	C18—C17—C16	118.36 (11)
C6—C7—H7A	110.1	N1—C18—C17	124.98 (14)
O1—C7—H7B	110.1	N1—C18—H18A	117.5
C6—C7—H7B	110.1	C17—C18—H18A	117.5
H7A—C7—H7B	108.4	N1—C19—C20	123.70 (15)
O1—C8—C13	124.89 (11)	N1—C19—H19A	118.2
O1—C8—C9	115.53 (11)	C20—C19—H19A	118.2
C13—C8—C9	119.58 (12)	C19—C20—C21	119.08 (15)
C10—C9—C8	120.64 (12)	C19—C20—H20A	120.5
C10—C9—H9A	119.7	C21—C20—H20A	120.5
C8—C9—H9A	119.7	C20—C21—C17	119.14 (14)
C9—C10—C11	120.79 (12)	C20—C21—H21A	120.4
C9—C10—H10A	119.6	C17—C21—H21A	120.4
C6—C1—C2—C3	0.0 (3)	C11—C12—C13—C8	0.9 (2)
C1—C2—C3—C4	−0.6 (3)	O1—C8—C13—C12	178.71 (12)
C2—C3—C4—C5	0.9 (3)	C9—C8—C13—C12	−0.9 (2)
C3—C4—C5—C6	−0.7 (2)	C12—C11—C14—C15	−178.19 (14)
C2—C1—C6—C5	0.2 (2)	C10—C11—C14—C15	0.7 (2)
C2—C1—C6—C7	−179.44 (14)	C11—C14—C15—C16	178.09 (13)
C4—C5—C6—C1	0.1 (2)	C14—C15—C16—O2	−8.9 (2)
C4—C5—C6—C7	179.77 (13)	C14—C15—C16—C17	172.68 (13)
C8—O1—C7—C6	−176.20 (12)	O2—C16—C17—C21	−176.13 (15)
C1—C6—C7—O1	−96.55 (15)	C15—C16—C17—C21	2.4 (2)
C5—C6—C7—O1	83.83 (16)	O2—C16—C17—C18	3.9 (2)
C7—O1—C8—C13	3.3 (2)	C15—C16—C17—C18	−177.67 (13)
C7—O1—C8—C9	−177.05 (12)	C19—N1—C18—C17	−0.2 (3)
O1—C8—C9—C10	−178.79 (12)	C21—C17—C18—N1	0.4 (2)
C13—C8—C9—C10	0.9 (2)	C16—C17—C18—N1	−179.58 (15)
C8—C9—C10—C11	−0.7 (2)	C18—N1—C19—C20	0.2 (3)
C9—C10—C11—C12	0.6 (2)	N1—C19—C20—C21	−0.4 (3)
C9—C10—C11—C14	−178.24 (13)	C19—C20—C21—C17	0.5 (3)
C10—C11—C12—C13	−0.7 (2)	C18—C17—C21—C20	−0.5 (2)
C14—C11—C12—C13	178.21 (13)	C16—C17—C21—C20	179.44 (15)