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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2753.
Published online 2010 October 9. doi:  10.1107/S1600536810039486
PMCID: PMC3009365

(E)-5,6-Dimeth­oxy-2-(pyridin-4-yl­methyl­idene)-2,3-dihydro-1H-inden-1-one

Abstract

The mol­ecule of the title compound, C17H15NO3, is slightly twisted, with a dihedral angle of 12.12 (3)° between the dihydro­indenone group and the pyridine ring. In the crystal, mol­ecules are connected into layers parallel to the ab plane via inter­molecular C—H(...)O hydrogen bonds. Weak π–π [centroid–centroid distance = 3.5680 (6) Å] inter­actions are also observed.

Related literature

For general background and the biological activity of chalcone derivatives, see: Nowakowska (2008 [triangle]); Akihisa et al. (2006 [triangle]); Narender et al. (2005 [triangle]); Zhang et al. (2006 [triangle]); Dicarlo et al. (1999 [triangle]); Heidenreich et al. (2008 [triangle]); Syed et al. (2008 [triangle]); D’Archivio et al. (2008 [triangle]). For a related structure, see: Ali et al. (2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-66-o2753-scheme1.jpg

Experimental

Crystal data

  • C17H15NO3
  • M r = 281.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2753-efi1.jpg
  • a = 10.7572 (14) Å
  • b = 8.6057 (11) Å
  • c = 17.2961 (17) Å
  • β = 123.394 (6)°
  • V = 1336.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.45 × 0.32 × 0.23 mm

Data collection

  • Bruker APEXII Duo CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.958, T max = 0.979
  • 21745 measured reflections
  • 5874 independent reflections
  • 5138 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.132
  • S = 1.10
  • 5874 reflections
  • 192 parameters
  • H-atom parameters constrained
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.27 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039486/rz2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039486/rz2492Isup2.hkl

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

Acknowledgments

The authors wish to express their thanks to Universiti Sains Malysia (USM) for providing research facilities. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160 and CSY thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Chalcone moieties are common substructures in numerous natural products belonging to the flavonoid family (Nowakowska, 2008; Akihisa et al. 2006; Narender et al., 2005; Zhang et al., 2006).Chalcone derivatives are very versatile as physiologically active compounds and substrates for the evaluation of various organic syntheses. Chalcones, one of the major classes of natural products with widespread distribution in spices, tea, beer, fruits and vegetables, have been recently subject of great interest for their pharmacological activities (Dicarlo et al., 2009). Prostate cancer is one of the most commonly diagnosed cancers in men, and the second leading cause of cancer deaths in the European Union and United States of America (Heidenreich et al., 2008). Many antitumor drugs have been developed for prostate cancer patients, but their intolerable systemic toxicity often limits their clinical use. Chemoprevention is one of the most promising approaches in prostate cancer research, in which natural or synthetic agents are used to prevent this malignant disease (Heidenreich et al., 2008; Syed et al., 2008; D'Archivio et al., 2008).

The molecular structure of the title compound is slightly twisted (Fig. 1). The torsion angles of the two methoxy groups are [C16–O2–C4–C5] -175.13 (6) and [C17–O3–C5–C4] -178.48 (6)°. The maximum deviation of the dihydroindenone group is 0.028 (1) Å and it makes dihedral angle of 12.12 (3)° with the pyridine ring [C11–C13/N1/C14–C15]. The geometry parameters are comparable to those observed in a closely related structure (Ali et al., 2010).

In the crystal structure, the molecules are linked together into chains by a bifurcated hydrogen bonds involving the intermolecular C14—H14A···O3 and C14—H14A···O3 hydrogen bonds (Table 1) generating a R21(5) ring motif. These chains are arranged in an anti-parallel layer (Fig. 2) and each pair of anti-parallel layers are interconnected into a two-dimensional plane parallel to ab plane via intermolecular C16—H16A···O1 hydrogen bonds (Fig. 3, Table 1). Weak π···π interactions are also observed [Cg1···Cg2iii of 3.5680 (6) Å; (iii) 1 - x, 1 - y, -z. Cg1 and Cg2 are centroids of C1–C2/C7–C9 and C2–C7 ring, respectively].

Experimental

A mixture of 5,6-dimethoxy-2,3-dihydro-1H-indene-1-one (0.001 mmol) and isonicotinaldehyde (0.001 mmol) were dissolved in methanol (10 ml) and 30% sodium hydroxide solution (5 ml) was added and the solution stirred for 5 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with concentrated HCl. The precipitated solid was filtered, washed with water and recrystallized from ethanol to reveal the title compound as light yellow crystals.

Refinement

All hydrogen atoms were positioned geometrically [C–H = 0.93–0.97 Å] and refined using a riding model with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating-group model was applied for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.
Fig. 2.
The crystal packing of title compound, showing chains arranged anti-parallelly. Intermolecular hydrogen bonds are shown as dashed lines.
Fig. 3.
The crystal packing of title compound, showing a two-dimensional plane parallel to ab plane. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C17H15NO3F(000) = 592
Mr = 281.30Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9933 reflections
a = 10.7572 (14) Åθ = 2.8–35.1°
b = 8.6057 (11) ŵ = 0.10 mm1
c = 17.2961 (17) ÅT = 100 K
β = 123.394 (6)°Block, yellow
V = 1336.8 (3) Å30.45 × 0.32 × 0.23 mm
Z = 4

Data collection

Bruker APEXII Duo CCD area-detector diffractometer5874 independent reflections
Radiation source: fine-focus sealed tube5138 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 35.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −17→17
Tmin = 0.958, Tmax = 0.979k = −13→13
21745 measured reflectionsl = −17→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0783P)2 + 0.2242P] where P = (Fo2 + 2Fc2)/3
5874 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = −0.26 e Å3

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 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.

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

xyzUiso*/Ueq
O10.32457 (7)0.81081 (8)−0.16256 (4)0.02006 (13)
O20.80183 (6)0.43182 (7)−0.05682 (4)0.01665 (11)
O30.92680 (6)0.42839 (7)0.11848 (4)0.01546 (11)
N10.16589 (8)1.13656 (9)0.15678 (5)0.01914 (13)
C10.41258 (8)0.78448 (8)−0.07968 (5)0.01273 (12)
C20.54736 (7)0.68903 (7)−0.03693 (4)0.01082 (11)
C30.60522 (8)0.60592 (8)−0.08026 (4)0.01211 (12)
H3A0.55870.6093−0.14420.015*
C40.73270 (7)0.51920 (8)−0.02574 (4)0.01175 (12)
C50.80361 (7)0.51765 (8)0.07250 (4)0.01137 (11)
C60.74738 (7)0.60432 (8)0.11466 (4)0.01135 (11)
H6A0.79550.60550.17870.014*
C70.61696 (7)0.68941 (7)0.05839 (4)0.01039 (11)
C80.53304 (8)0.78599 (8)0.08831 (4)0.01196 (12)
H8A0.50180.72330.12130.014*
H8B0.59340.87170.12750.014*
C90.40070 (7)0.84391 (8)−0.00227 (4)0.01164 (11)
C100.28495 (8)0.93423 (8)−0.02118 (5)0.01312 (12)
H10A0.21760.9567−0.08350.016*
C110.24992 (7)1.00219 (8)0.04230 (5)0.01233 (12)
C120.31954 (9)0.96061 (10)0.13540 (5)0.01933 (15)
H12A0.39650.88830.16180.023*
C130.27285 (10)1.02821 (11)0.18809 (6)0.02310 (17)
H13A0.31880.99620.24930.028*
C140.10022 (8)1.17804 (9)0.06768 (5)0.01567 (13)
H14A0.02621.25360.04400.019*
C150.13705 (8)1.11388 (8)0.00888 (5)0.01385 (12)
H15A0.08661.1453−0.05270.017*
C160.74321 (9)0.43840 (10)−0.15362 (5)0.01808 (14)
H16A0.80140.3730−0.16700.027*
H16B0.74710.5435−0.17080.027*
H16C0.64180.4032−0.18810.027*
C171.00081 (9)0.41893 (10)0.21693 (5)0.01939 (14)
H17A1.08490.35050.24150.029*
H17B0.93300.37940.23190.029*
H17C1.03420.52050.24340.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0204 (3)0.0275 (3)0.0098 (2)0.0087 (2)0.0067 (2)0.00324 (19)
O20.0182 (2)0.0220 (3)0.0120 (2)0.00551 (19)0.00975 (19)−0.00182 (18)
O30.0142 (2)0.0200 (2)0.0111 (2)0.00625 (18)0.00627 (18)0.00077 (17)
N10.0189 (3)0.0226 (3)0.0175 (3)0.0056 (2)0.0109 (2)−0.0015 (2)
C10.0138 (3)0.0142 (3)0.0106 (3)0.0021 (2)0.0070 (2)0.0008 (2)
C20.0119 (2)0.0118 (2)0.0096 (2)0.00066 (19)0.0065 (2)−0.00052 (19)
C30.0132 (3)0.0140 (3)0.0095 (2)0.0003 (2)0.0065 (2)−0.00105 (19)
C40.0130 (3)0.0135 (3)0.0106 (2)0.0005 (2)0.0076 (2)−0.00177 (19)
C50.0115 (2)0.0128 (3)0.0104 (2)0.00140 (19)0.0064 (2)−0.00031 (19)
C60.0122 (2)0.0129 (3)0.0095 (2)0.00100 (19)0.0063 (2)−0.00042 (19)
C70.0118 (2)0.0111 (2)0.0094 (2)0.00076 (19)0.0066 (2)−0.00013 (18)
C80.0136 (3)0.0131 (3)0.0101 (2)0.0024 (2)0.0071 (2)0.00030 (19)
C90.0131 (3)0.0122 (3)0.0105 (2)0.0015 (2)0.0071 (2)0.00038 (19)
C100.0138 (3)0.0144 (3)0.0115 (3)0.0024 (2)0.0072 (2)0.0007 (2)
C110.0121 (3)0.0128 (3)0.0129 (3)0.0015 (2)0.0074 (2)−0.0003 (2)
C120.0212 (3)0.0241 (3)0.0141 (3)0.0106 (3)0.0105 (3)0.0025 (2)
C130.0249 (4)0.0309 (4)0.0149 (3)0.0132 (3)0.0118 (3)0.0027 (3)
C140.0146 (3)0.0147 (3)0.0185 (3)0.0023 (2)0.0096 (3)−0.0008 (2)
C150.0131 (3)0.0139 (3)0.0154 (3)0.0019 (2)0.0083 (2)0.0009 (2)
C160.0212 (3)0.0235 (3)0.0127 (3)0.0006 (3)0.0113 (3)−0.0035 (2)
C170.0184 (3)0.0259 (4)0.0118 (3)0.0083 (3)0.0070 (2)0.0035 (2)

Geometric parameters (Å, °)

O1—C11.2283 (8)C8—H8A0.9700
O2—C41.3593 (8)C8—H8B0.9700
O2—C161.4289 (9)C9—C101.3465 (9)
O3—C51.3486 (8)C10—C111.4646 (10)
O3—C171.4310 (9)C10—H10A0.9300
N1—C131.3419 (10)C11—C121.3980 (10)
N1—C141.3427 (10)C11—C151.3999 (10)
C1—C21.4640 (10)C12—C131.3874 (11)
C1—C91.5029 (9)C12—H12A0.9300
C2—C71.3857 (9)C13—H13A0.9300
C2—C31.4050 (9)C14—C151.3928 (10)
C3—C41.3796 (9)C14—H14A0.9300
C3—H3A0.9300C15—H15A0.9300
C4—C51.4291 (9)C16—H16A0.9600
C5—C61.3926 (9)C16—H16B0.9600
C6—C71.3959 (9)C16—H16C0.9600
C6—H6A0.9300C17—H17A0.9600
C7—C81.5124 (9)C17—H17B0.9600
C8—C91.5081 (9)C17—H17C0.9600
C4—O2—C16117.18 (6)C1—C9—C8108.57 (5)
C5—O3—C17117.17 (6)C9—C10—C11129.30 (6)
C13—N1—C14116.14 (7)C9—C10—H10A115.3
O1—C1—C2127.28 (6)C11—C10—H10A115.3
O1—C1—C9126.02 (6)C12—C11—C15116.38 (6)
C2—C1—C9106.69 (5)C12—C11—C10124.44 (6)
C7—C2—C3121.87 (6)C15—C11—C10119.16 (6)
C7—C2—C1109.63 (5)C13—C12—C11119.41 (7)
C3—C2—C1128.51 (6)C13—C12—H12A120.3
C4—C3—C2118.44 (6)C11—C12—H12A120.3
C4—C3—H3A120.8N1—C13—C12124.49 (7)
C2—C3—H3A120.8N1—C13—H13A117.8
O2—C4—C3125.68 (6)C12—C13—H13A117.8
O2—C4—C5114.52 (6)N1—C14—C15123.45 (7)
C3—C4—C5119.80 (6)N1—C14—H14A118.3
O3—C5—C6124.43 (6)C15—C14—H14A118.3
O3—C5—C4114.50 (6)C14—C15—C11120.09 (7)
C6—C5—C4121.07 (6)C14—C15—H15A120.0
C5—C6—C7118.39 (6)C11—C15—H15A120.0
C5—C6—H6A120.8O2—C16—H16A109.5
C7—C6—H6A120.8O2—C16—H16B109.5
C2—C7—C6120.38 (6)H16A—C16—H16B109.5
C2—C7—C8112.02 (6)O2—C16—H16C109.5
C6—C7—C8127.58 (6)H16A—C16—H16C109.5
C9—C8—C7103.07 (5)H16B—C16—H16C109.5
C9—C8—H8A111.1O3—C17—H17A109.5
C7—C8—H8A111.1O3—C17—H17B109.5
C9—C8—H8B111.1H17A—C17—H17B109.5
C7—C8—H8B111.1O3—C17—H17C109.5
H8A—C8—H8B109.1H17A—C17—H17C109.5
C10—C9—C1120.04 (6)H17B—C17—H17C109.5
C10—C9—C8131.39 (6)
O1—C1—C2—C7179.48 (7)C5—C6—C7—C2−1.08 (10)
C9—C1—C2—C7−1.11 (8)C5—C6—C7—C8177.43 (6)
O1—C1—C2—C3−0.64 (12)C2—C7—C8—C90.57 (7)
C9—C1—C2—C3178.78 (7)C6—C7—C8—C9−178.05 (7)
C7—C2—C3—C41.86 (10)O1—C1—C9—C100.39 (12)
C1—C2—C3—C4−178.02 (7)C2—C1—C9—C10−179.04 (6)
C16—O2—C4—C34.42 (10)O1—C1—C9—C8−179.11 (7)
C16—O2—C4—C5−175.13 (6)C2—C1—C9—C81.46 (7)
C2—C3—C4—O2179.51 (6)C7—C8—C9—C10179.35 (7)
C2—C3—C4—C5−0.96 (10)C7—C8—C9—C1−1.23 (7)
C17—O3—C5—C62.22 (10)C1—C9—C10—C11178.89 (7)
C17—O3—C5—C4−178.48 (6)C8—C9—C10—C11−1.74 (13)
O2—C4—C5—O3−0.69 (9)C9—C10—C11—C12−12.38 (13)
C3—C4—C5—O3179.73 (6)C9—C10—C11—C15169.28 (7)
O2—C4—C5—C6178.64 (6)C15—C11—C12—C131.08 (12)
C3—C4—C5—C6−0.94 (10)C10—C11—C12—C13−177.30 (8)
O3—C5—C6—C7−178.78 (6)C14—N1—C13—C121.08 (14)
C4—C5—C6—C71.96 (10)C11—C12—C13—N1−1.95 (15)
C3—C2—C7—C6−0.83 (10)C13—N1—C14—C150.58 (12)
C1—C2—C7—C6179.06 (6)N1—C14—C15—C11−1.33 (12)
C3—C2—C7—C8−179.56 (6)C12—C11—C15—C140.43 (11)
C1—C2—C7—C80.33 (8)C10—C11—C15—C14178.90 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14A···O2i0.932.573.4787 (12)167
C14—H14A···O3i0.932.573.2708 (12)133
C16—H16A···O1ii0.962.533.0486 (11)114

Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, y−1/2, −z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2492).

References

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