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Acta Cryst. (2010). E66, o2878    [ doi:10.1107/S1600536810041723 ]

(E)-2-[4-(Piperidin-1-yl)benzylidene]-2,3-dihydro-1H-inden-1-one

M. A. Ali, R. Ismail, T. S. Choon, M. M. Rosli and H.-K. Fun

Abstract top

In the title compound, C21H21NO, the indene ring system is essentially planar with a maximum deviation of 0.066 (1) Å and makes dihedral angles of 7.93 (6) and 2.43 (6)°, respectively, with the benzene plane and the mean plane of the piperidine ring. These latter two planes make a dihedral angle of 7.61 (7)°. In the crystal, molecules are linked by C-H...O interactions, forming infinite chains along the b axis.

Comment top

Chalcones are well known intermediates for synthesizing various heterocyclic compounds. The compounds with the backbone of chalcones have been reported to possess various biological activities. The presence of a reactive unsaturated keto function in chalcones is found to be responsible for their various biological activities. Chalcone derivatives are very versatile as physiologically active compounds and substrates for the evaluation of various organic syntheses. Chalcones belong to one of the major classes of natural products with widespread distribution in spices, tea, beer, fruits and vegetables. Chalcones also have been recently the subject of great interests for their pharmacological activities (Di Carlo et al., 1999). 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).

All parameters in the title compound, (I), are within normal ranges. The indene group is planar with the maximum deviation of 0.066 (1) Å for atom C9 and make dihedral angle of 7.93 (6) and 2.43 (6)° respectively with the C11-C16 benzene and N1/C17-C21 piperidine rings. The dihedral angle between the C11-C16 benzene ring and N1/C17-C21 piperidine ring is 7.61 (7)°.

In the crystal structure, the molecules are linked by C8—H8A···O1i (Table 1) interactions to form infinite chains along the b-axis.

Related literature top

For the biological activity of chalcones, see: Di Carlo et al. (1999). For background to prostate cancer, see: Heidenreich et al. (2008); Syed et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2,3-dihydro-1H-indene-1-one (0.001 mmol) and 4-(piperidin-1-yl)benzaldehyde (0.001 mmol) were dissolved in methanol (10 mL) and 30% sodium hydroxide solution (5ml) was added and the mixture stirred for 5 hour. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with Con HCl. The precipitated solid was filtered, washed with water and recrystallised from ethanol to reveal the title compound as light yellow crystals.

Refinement top

All H atoms were positioned geometrically and refined using a riding model [C—H = 0.93 Å for Csp2 and 0.97 Å for methine C]; Uiso(H) = 1.2Ueq(C) for all H atoms. In the absence of significant anomalous dispersion,1848 Friedel pairs were merged in the final refinement.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of (I) viewed along the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
(E)-2-[4-(Piperidin-1-yl)benzylidene]-2,3-dihydro-1H-inden-1-one top
Crystal data top
C21H21NOF(000) = 648
Mr = 303.39Dx = 1.288 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3558 reflections
a = 31.587 (5) Åθ = 2.9–31.5°
b = 6.3168 (10) ŵ = 0.08 mm−1
c = 7.8396 (12) ÅT = 100 K
V = 1564.2 (4) Å3Plate, yellow
Z = 40.48 × 0.44 × 0.09 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		2764 independent reflections
Radiation source: fine-focus sealed tube2563 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 31.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −40→46
Tmin = 0.963, Tmax = 0.993k = −9→9
9828 measured reflectionsl = −11→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.0999P]
where P = (Fo2 + 2Fc2)/3
2764 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.33 e Å−3
1 restraintΔρmin = −0.19 e Å−3
Crystal data top
C21H21NOV = 1564.2 (4) Å3
Mr = 303.39Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 31.587 (5) ŵ = 0.08 mm−1
b = 6.3168 (10) ÅT = 100 K
c = 7.8396 (12) Å0.48 × 0.44 × 0.09 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		2764 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2563 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.993Rint = 0.031
9828 measured reflectionsθmax = 31.5°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.33 e Å−3
S = 1.05Δρmin = −0.19 e Å−3
2764 reflectionsAbsolute structure: ?
208 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.17945 (3)1.37433 (17)0.61883 (16)0.0241 (2)
N10.04981 (4)0.63258 (19)0.61569 (17)0.0179 (2)
C1−0.18171 (4)1.1957 (2)0.55722 (18)0.0184 (3)
C2−0.22001 (4)1.0902 (2)0.48828 (18)0.0179 (3)
C3−0.26187 (5)1.1607 (3)0.4895 (2)0.0218 (3)
H3A−0.26891.29320.53260.026*
C4−0.29267 (5)1.0262 (3)0.4242 (2)0.0241 (3)
H4A−0.32091.06800.42550.029*
C5−0.28173 (5)0.8288 (3)0.3566 (2)0.0231 (3)
H5A−0.30280.74250.31120.028*
C6−0.23996 (4)0.7590 (3)0.3560 (2)0.0217 (3)
H6A−0.23290.62740.31120.026*
C7−0.20910 (4)0.8912 (2)0.42409 (19)0.0184 (3)
C8−0.16237 (5)0.8473 (2)0.4457 (2)0.0200 (3)
H8A−0.15780.72020.51260.024*
H8B−0.14860.83120.33600.024*
C9−0.14622 (4)1.0408 (2)0.53840 (18)0.0176 (3)
C10−0.10770 (4)1.0829 (2)0.60425 (19)0.0186 (3)
H10A−0.10551.21370.65790.022*
C11−0.06892 (4)0.9572 (2)0.60519 (18)0.0175 (3)
C12−0.06350 (5)0.7587 (2)0.52658 (19)0.0196 (3)
H12A−0.08650.69640.47210.023*
C13−0.02498 (5)0.6529 (2)0.52761 (19)0.0191 (3)
H13A−0.02270.52340.47190.023*
C140.01083 (4)0.7381 (2)0.61163 (17)0.0169 (2)
C150.00507 (5)0.9344 (2)0.6943 (2)0.0228 (3)
H15A0.02760.99480.75340.027*
C16−0.03344 (4)1.0388 (3)0.6890 (2)0.0224 (3)
H16A−0.03581.16900.74350.027*
C170.05603 (5)0.4579 (2)0.4944 (2)0.0214 (3)
H17A0.05750.51490.37970.026*
H17B0.03180.36350.50000.026*
C180.09625 (5)0.3320 (2)0.5307 (2)0.0219 (3)
H18A0.09270.25430.63640.026*
H18B0.10060.22990.43990.026*
C190.13536 (5)0.4725 (2)0.5447 (2)0.0226 (3)
H19A0.15980.38800.57590.027*
H19B0.14110.53970.43580.027*
C200.12720 (5)0.6394 (2)0.6797 (2)0.0198 (3)
H20A0.15140.73380.68640.024*
H20B0.12390.57140.78990.024*
C210.08766 (5)0.7671 (2)0.6395 (2)0.0203 (3)
H21A0.08240.86590.73180.024*
H21B0.09250.84870.53650.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (5)0.0152 (5)0.0289 (5)0.0000 (4)0.0002 (5)−0.0022 (4)
N10.0192 (5)0.0134 (5)0.0211 (5)−0.0015 (4)−0.0024 (4)−0.0024 (5)
C10.0204 (6)0.0165 (6)0.0182 (6)−0.0006 (5)0.0019 (5)0.0018 (5)
C20.0190 (6)0.0168 (6)0.0179 (5)−0.0003 (5)0.0008 (5)0.0010 (5)
C30.0215 (7)0.0227 (7)0.0213 (6)0.0037 (5)0.0003 (5)0.0011 (6)
C40.0196 (6)0.0317 (8)0.0210 (6)0.0000 (6)−0.0004 (5)0.0035 (7)
C50.0218 (7)0.0283 (8)0.0190 (6)−0.0054 (6)−0.0012 (5)0.0015 (6)
C60.0234 (7)0.0204 (7)0.0212 (6)−0.0042 (5)0.0000 (5)−0.0010 (6)
C70.0188 (6)0.0189 (6)0.0174 (6)−0.0017 (5)0.0009 (5)0.0004 (5)
C80.0195 (6)0.0171 (6)0.0232 (6)0.0008 (5)0.0014 (5)−0.0032 (5)
C90.0199 (6)0.0148 (6)0.0182 (6)−0.0001 (5)0.0024 (5)0.0001 (5)
C100.0215 (6)0.0165 (6)0.0178 (6)−0.0010 (5)0.0018 (5)−0.0015 (6)
C110.0193 (6)0.0169 (6)0.0163 (5)−0.0014 (5)0.0010 (5)−0.0001 (5)
C120.0200 (6)0.0178 (6)0.0209 (6)−0.0036 (5)−0.0023 (5)−0.0025 (5)
C130.0226 (6)0.0139 (6)0.0209 (6)−0.0019 (5)−0.0024 (5)−0.0024 (5)
C140.0197 (6)0.0150 (6)0.0160 (6)−0.0012 (5)−0.0009 (5)0.0004 (5)
C150.0203 (6)0.0199 (6)0.0283 (7)−0.0004 (6)−0.0039 (6)−0.0079 (6)
C160.0210 (6)0.0213 (7)0.0249 (6)0.0003 (6)−0.0001 (6)−0.0084 (6)
C170.0271 (7)0.0149 (6)0.0222 (6)0.0024 (5)−0.0059 (5)−0.0035 (5)
C180.0279 (7)0.0149 (6)0.0230 (6)0.0037 (5)−0.0028 (6)−0.0016 (6)
C190.0252 (7)0.0197 (7)0.0229 (6)0.0033 (6)0.0022 (5)−0.0006 (6)
C200.0199 (6)0.0173 (6)0.0222 (6)−0.0005 (5)−0.0003 (5)−0.0008 (5)
C210.0197 (6)0.0147 (6)0.0265 (7)−0.0023 (5)−0.0025 (5)−0.0017 (5)
Geometric parameters (Å, °) top
O1—C11.2297 (18)C11—C121.407 (2)
N1—C141.4004 (17)C12—C131.388 (2)
N1—C171.4697 (19)C12—H12A0.9300
N1—C211.4785 (17)C13—C141.4151 (18)
C1—C21.483 (2)C13—H13A0.9300
C1—C91.4951 (19)C14—C151.411 (2)
C2—C31.395 (2)C15—C161.384 (2)
C2—C71.397 (2)C15—H15A0.9300
C3—C41.389 (2)C16—H16A0.9300
C3—H3A0.9300C17—C181.525 (2)
C4—C51.399 (2)C17—H17A0.9700
C4—H4A0.9300C17—H17B0.9700
C5—C61.391 (2)C18—C191.525 (2)
C5—H5A0.9300C18—H18A0.9700
C6—C71.390 (2)C18—H18B0.9700
C6—H6A0.9300C19—C201.516 (2)
C7—C81.512 (2)C19—H19A0.9700
C8—C91.511 (2)C19—H19B0.9700
C8—H8A0.9700C20—C211.520 (2)
C8—H8B0.9700C20—H20A0.9700
C9—C101.3482 (19)C20—H20B0.9700
C10—C111.4601 (19)C21—H21A0.9700
C10—H10A0.9300C21—H21B0.9700
C11—C161.3977 (19)
C14—N1—C17117.39 (12)C12—C13—C14121.35 (13)
C14—N1—C21116.13 (11)C12—C13—H13A119.3
C17—N1—C21113.90 (12)C14—C13—H13A119.3
O1—C1—C2127.06 (13)N1—C14—C15121.40 (12)
O1—C1—C9126.56 (13)N1—C14—C13122.18 (12)
C2—C1—C9106.38 (12)C15—C14—C13116.41 (12)
C3—C2—C7121.54 (14)C16—C15—C14121.22 (13)
C3—C2—C1128.86 (14)C16—C15—H15A119.4
C7—C2—C1109.53 (12)C14—C15—H15A119.4
C4—C3—C2117.79 (14)C15—C16—C11122.87 (14)
C4—C3—H3A121.1C15—C16—H16A118.6
C2—C3—H3A121.1C11—C16—H16A118.6
C3—C4—C5120.79 (14)N1—C17—C18112.47 (12)
C3—C4—H4A119.6N1—C17—H17A109.1
C5—C4—H4A119.6C18—C17—H17A109.1
C6—C5—C4121.20 (14)N1—C17—H17B109.1
C6—C5—H5A119.4C18—C17—H17B109.1
C4—C5—H5A119.4H17A—C17—H17B107.8
C7—C6—C5118.27 (14)C19—C18—C17112.63 (12)
C7—C6—H6A120.9C19—C18—H18A109.1
C5—C6—H6A120.9C17—C18—H18A109.1
C6—C7—C2120.39 (14)C19—C18—H18B109.1
C6—C7—C8128.13 (14)C17—C18—H18B109.1
C2—C7—C8111.45 (13)H18A—C18—H18B107.8
C9—C8—C7103.59 (12)C20—C19—C18108.49 (12)
C9—C8—H8A111.0C20—C19—H19A110.0
C7—C8—H8A111.0C18—C19—H19A110.0
C9—C8—H8B111.0C20—C19—H19B110.0
C7—C8—H8B111.0C18—C19—H19B110.0
H8A—C8—H8B109.0H19A—C19—H19B108.4
C10—C9—C1120.65 (13)C19—C20—C21111.33 (12)
C10—C9—C8130.43 (13)C19—C20—H20A109.4
C1—C9—C8108.88 (12)C21—C20—H20A109.4
C9—C10—C11130.66 (13)C19—C20—H20B109.4
C9—C10—H10A114.7C21—C20—H20B109.4
C11—C10—H10A114.7H20A—C20—H20B108.0
C16—C11—C12115.92 (13)N1—C21—C20112.69 (11)
C16—C11—C10118.30 (13)N1—C21—H21A109.1
C12—C11—C10125.77 (13)C20—C21—H21A109.1
C13—C12—C11122.20 (13)N1—C21—H21B109.1
C13—C12—H12A118.9C20—C21—H21B109.1
C11—C12—H12A118.9H21A—C21—H21B107.8
O1—C1—C2—C3−5.5 (3)C9—C10—C11—C16−177.96 (16)
C9—C1—C2—C3174.07 (14)C9—C10—C11—C122.9 (3)
O1—C1—C2—C7177.72 (15)C16—C11—C12—C13−1.8 (2)
C9—C1—C2—C7−2.73 (16)C10—C11—C12—C13177.35 (14)
C7—C2—C3—C4−0.1 (2)C11—C12—C13—C141.4 (2)
C1—C2—C3—C4−176.58 (15)C17—N1—C14—C15−165.73 (14)
C2—C3—C4—C5−1.2 (2)C21—N1—C14—C15−26.1 (2)
C3—C4—C5—C61.4 (2)C17—N1—C14—C1315.4 (2)
C4—C5—C6—C7−0.2 (2)C21—N1—C14—C13155.05 (13)
C5—C6—C7—C2−1.1 (2)C12—C13—C14—N1179.27 (13)
C5—C6—C7—C8176.75 (15)C12—C13—C14—C150.3 (2)
C3—C2—C7—C61.3 (2)N1—C14—C15—C16179.56 (14)
C1—C2—C7—C6178.40 (13)C13—C14—C15—C16−1.5 (2)
C3—C2—C7—C8−176.88 (14)C14—C15—C16—C111.0 (3)
C1—C2—C7—C80.19 (17)C12—C11—C16—C150.6 (2)
C6—C7—C8—C9−175.67 (15)C10—C11—C16—C15−178.60 (15)
C2—C7—C8—C92.37 (16)C14—N1—C17—C18−170.28 (13)
O1—C1—C9—C105.7 (2)C21—N1—C17—C1849.17 (17)
C2—C1—C9—C10−173.86 (13)N1—C17—C18—C19−52.23 (18)
O1—C1—C9—C8−176.22 (15)C17—C18—C19—C2055.49 (17)
C2—C1—C9—C84.22 (15)C18—C19—C20—C21−56.53 (16)
C7—C8—C9—C10173.83 (15)C14—N1—C21—C20167.89 (13)
C7—C8—C9—C1−4.00 (15)C17—N1—C21—C20−51.05 (17)
C1—C9—C10—C11178.71 (14)C19—C20—C21—N155.19 (17)
C8—C9—C10—C111.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.972.443.3256 (18)152
Symmetry codes: (i) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.972.443.3256 (18)152
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

The authors wish to express their thanks to Universiti Sains Malaysia (USM) for providing research facilities. HKF and MMR also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

references
References top

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