N-[(1-Benzoyl­piperidin-4-yl)meth­yl]benzamide

K Prathebha; D Reuben Jonathan; Sathya Shanmugam; G Usha

doi:10.1107/S1600536814012793

. 2014 Jun 14;70(Pt 7):o771. doi: 10.1107/S1600536814012793

N-[(1-Benzoylpiperidin-4-yl)methyl]benzamide

K Prathebha ^a, D Reuben Jonathan ^b, Sathya Shanmugam ^a, G Usha ^a,^*

PMCID: PMC4120622 PMID: 25161560

Abstract

In the title compound, C₂₀H₂₂N₂O₂, the piperidine ring adopts a chair conformation. The phenyl rings are inclined to one another by 80.1 (1)° and make dihedral angles of 46.1 (1) and 40.2 (1)° with the mean plane of the piperidine ring. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers. C—H⋯O interactions further link the molecules, forming a three-dimensional supramolecular network.

Related literature

For the synthesis of the title compound, see: Prathebha et al. (2013 ▶); Venkatraj et al. (2008 ▶). For the biological activity of piperdine derivatives, see: Ramalingan et al. (2004 ▶); Sergeant & May (1970 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Al-abbasi et al. (2010 ▶); Ávila et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). graphic file with name e-70-0o771-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₂N₂O₂
M _r = 322.40
Triclinic,
a = 9.8039 (2) Å
b = 10.4453 (2) Å
c = 10.6765 (2) Å
α = 62.208 (1)°
β = 66.009 (1)°
γ = 68.150 (1)°
V = 860.80 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.982, T _max = 0.984
12912 measured reflections
3562 independent reflections
2929 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.125
S = 1.04
3531 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012793/bt6968sup1.cif

e-70-0o771-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012793/bt6968Isup2.hkl

e-70-0o771-Isup2.hkl^{(169.6KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814012793/bt6968Isup3.cml

CCDC reference: 987515

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.97	2.60	3.5548 (18)	169
C3—H3⋯O2ⁱⁱ	0.93	2.47	3.3803 (17)	167
N2—H2A⋯O2ⁱⁱ	0.86	2.11	2.9401 (15)	162
C8—H8⋯O1ⁱⁱⁱ	0.93	2.52	3.4506 (19)	176

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

Acknowledgments

The authors thank Professor Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

supplementary crystallographic information

S1. Comment

Biologically active alkaloids of substituted piperidines have been targeted for their total or partial synthesis (Ramalingan et al., 2004). Piperidines are known to have CNS depressant action at low dosage levels and stimulant activity with increased doses. In addition, the nucleus also possesses analgesic, anglionic blocking and anesthetic properties as well (Sergeant & May, 1970). We report in this communication, the synthesis and crystal structure of a new piperidine derivative.

The phenyl rings form dihedral angles of 46.1 (1)° and 40.2 (1)°, respectively, with the best plane through the piperidine ring atoms. The C—N distances [1.337 (2)- 1.468 (2) Å] are in the normal range and are in good agreement with values of a similar reported structure (Ávila et al., 2010). The piperdine ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) of q2 = 0.0351 (1) Å, phi2 = -50.61 (3)° q3 = 0.5633 (1) Å, QT = 0.5644 (2) Å and θ2 = 3.67 (2)°.

The crystal packing shows N-H···O hydrogen bonds linking the molecules to centrosymmetric dimers (Fig. 2).

S2. Experimental

The procedure (Prathebha et al., 2013, Venkatraj et al., 2008) adopted in the synthesis of the typical diamide is as follows: In a 250 mL round-bottomed flask 4-methyl piperidine (0.01 mol) was taken in, to which 100 mL of ethyl methyl ketone was added and stirred at room temperature. After 5 minutes, triethylamine (0.02 mol) was added and the mixture was stirred for 15 minutes. Then, benzoyl chloride (0.02 mol) was added and the reaction mixture was stirred at room temperature for about 2 h. A white precipitate of triethyl ammonium chloride was formed. It was filtered and the filterate was evaporated to get the crude product. The crude product was recrystallized twice from ethyl methyl ketone. Melting Point: 127 °C, yield: 85%.