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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Aug 15;68(Pt 9):o2724. doi: 10.1107/S1600536812034897

(2E)-3-[4-(Benz­yloxy)phen­yl]-1-(pyridin-3-yl)prop-2-en-1-one

Hoong-Kun Fun a,*,‡, Ching Kheng Quah a,§, Prakash S Nayak b, B Narayana b, B K Sarojini c
PMCID: PMC3435737  PMID: 22969608

Abstract

The title compound, C21H17NO2, 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 inter­molecular inter­actions 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 ▶).graphic file with name e-68-o2724-scheme1.jpg

Experimental  

Crystal data  

  • C21H17NO2

  • M r = 315.36

  • Monoclinic, Inline graphic

  • 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 ▶).

Supplementary Material

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

e-68-o2724-sup1.cif (25.6KB, cif)

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

e-68-o2724-Isup2.hkl (232.8KB, hkl)

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

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

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

supplementary crystallographic information

Comment

Chalcones constitute an important family of substances belonging to flavonoids and isoflavonoids and are abundant in edible plants. Chalcones exhibit many pharmacological activities, including anti-leishmanial, anti-inflammatory (Matsuda et al., 2003), anti-mitotic, anti-invasive, anti-tuberculosis, anti-fungal (Lopez et al., 2001) and anti-malarial (Agarwal et al., 2005). Nitrogen moiety containing heterocyclic chalcones plays important roles as anti-ulcer, herbicidal, anti-bacterial, analgesic, sedative, anti-phlogistic and virucidal agents. The crystal structures of some chalcones derived from acetyl pyridine viz., (Z)-3-(2,6-dichlorophenyl)-1-(pyridin-3-yl)-2- (1H-1,2,4-triazol-1-yl)prop-2-en-1-one (Liu et al., 2005), 3-(3-chlorophenyl)-1-(2-methylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-one (Bibila Mayaya Bisseyou et al., 2007) and (2E)-3-(3-bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In continuation of our studies on chalcones and their derivatives, the title compound (I) was prepared and its crystal structure is reported.

The title compound (Fig. 1) exists in an E configuration with respect to the C14═C15 bond [1.3217 (19) Å]. The pyridin-3-yl ring (N1/C17–C21) forms dihedral angles of 5.57 (7) and 82.30 (9)° with the benzene (C8–C13) and phenyl (C1–C6) rings, respectively. The dihedral angle between the benzene and phenyl rings is 87.69 (8)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Bibila Mayaya Bisseyou et al., 2007; Liu et al., 2005; Jasinski et al., 2011). No significant intermolecular hydrogen bonds are observed.

Experimental

To a mixture of 3-acetylpyridine (1.1 mL, 0.01 mol) and 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) in ethanol (100 mL), 15 mL of 10% sodium hydroxide solution was added and stirred at 0–5 °C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from acetone and toluene (1:1) mixture by slow evaporation method (m.p. 403–407 K).

Refinement

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 or 0.99 Å and Uiso(H) = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.

Crystal data

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
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Data collection

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
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Refinement

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
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5181).

References

  1. Agarwal, A., Srivastava, K., Puri, S. K. & Chauhan, P. M. S. (2005). Bioorg. Med. Chem. 13, 4645–4650. [DOI] [PubMed]
  2. Bibila Mayaya Bisseyou, Y., Soro, A. P., Sissouma, D., Giorgi, M. & Ebby, N. (2007). Acta Cryst. E63, o4758–o4759.
  3. Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  5. Jasinski, J. P., Butcher, R. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o352–o353. [DOI] [PMC free article] [PubMed]
  6. Liu, J.-B., Dai, H., Tao, W.-F., Jin, Z. & Fang, J.-X. (2005). Acta Cryst. E61, o3599–o3601.
  7. Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Jaime, C. C., Cortes, J. C. G., Ribas, J. C., Devia, C., Ana, M. R. & Ricardo, D. E. (2001). Bioorg. Med. Chem. 9, 1999–2013. [DOI] [PubMed]
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  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-68-o2724-sup1.cif (25.6KB, cif)

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

e-68-o2724-Isup2.hkl (232.8KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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