(2E)-3-(3-Nitro­phen­yl)-1-[4-(piperidin-1-yl)phen­yl]prop-2-en-1-one

Hoong-Kun Fun; Tze Shyang Chia; Prakash S Nayak; B Narayana; B K Sarojini

doi:10.1107/S1600536812008847

. 2012 Mar 7;68(Pt 4):o974. doi: 10.1107/S1600536812008847

(2E)-3-(3-Nitrophenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Prakash S Nayak ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3343948 PMID: 22590029

Abstract

In the title compound, C₂₀H₂₀N₂O₃, the piperidine ring adopts a chair conformation and its mean plane forms dihedral angles of 19.63 (9) and 19.44 (9)°, respectively, with the benzene and the nitro-substituted benzene ring. The benzene and nitro-substituted benzene rings are almost coplanar and make a dihedral angle of 4.78 (8)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into two-dimensional networks parallel to the ab plane. The crystal packing is further stabilized by π–π interactions [maximum centroid–centroid distance = 3.7807 (12) Å].

Related literature

For related structures and background to chalcones, see: Fun et al. (2011a ▶,b ▶,c ▶,d ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₂₀N₂O₃
M _r = 336.38
Orthorhombic,
a = 7.4268 (12) Å
b = 11.3884 (18) Å
c = 39.447 (6) Å
V = 3336.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.22 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.973, T _max = 0.990
20847 measured reflections
4870 independent reflections
3174 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.154
S = 1.04
4870 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 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/S1600536812008847/ds2176sup1.cif

e-68-0o974-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008847/ds2176Isup2.hkl

e-68-0o974-Isup2.hkl^{(238.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008847/ds2176Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3ⁱ	0.93	2.55	3.441 (2)	161
C16—H16A⋯O1ⁱⁱ	0.93	2.45	3.358 (2)	164

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PSKBP/8630013). BN thanks the UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of chalcones (Fun et al., 2011a,b,c,d), the crystal structure of the title compound is reported here.

In the title compound (Fig. 1), the piperidine ring (N1/C1–C5) adopts a chair conformation [puckering parameters Q = 0.551 (2) Å, θ = 1.6 (2)° and φ = 233 (7)° (Cremer & Pople, 1975)] and form dihedral angles of 19.63 (9) and 19.44 (9)°, respectively with the benzene (C6–C11) and nitro-substituted benzene (C15–C20) ring. The essentially planar benzene [maximum deviation = 0.007 (1) Å at atoms C9 and C10] and nitro-substituted benzene ring [maximum deviation = 0.008 (2) Å at atom C17] are coplanar with each other, forming a dihedral angle of 4.78 (8)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b,c,d).

In the crystal packing, the molecules are linked by intermolecular C—H···O hydrogen bonds into two-dimensional networks parallel to ab plane. The crystal packing is further stabilized by π–π interactions with Cg2···Cg3 = 3.7807 (12) and 3.7043 (12) Å (symmetry code = 1-X,1-Y,-Z and 2-X,1-Y,-Z, respectively), where Cg2 and Cg3 are the centroids of C6–C11 and C15–C20 rings respectively.

Experimental

To a mixture of 4-piperidinoacetophenone (2.03 g, 0.01 mol) and 3-nitrobenzaldehyde (1.51 g, 0.01 mol) in ethanol (50 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10 °C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from mixture of acetone and toluene solvent by slow evaporation method (M.P.: 365–369 K).