Crystal structure of 4-methyl-N-[2-(piperidin-1-yl)eth­yl]benzamide monohydrate

B K Revathi; D Reuben Jonathan; S Sathya; K Prathebha; G Usha

doi:10.1107/S2056989015007653

. 2015 Apr 30;71(Pt 5):o359–o360. doi: 10.1107/S2056989015007653

Crystal structure of 4-methyl-N-[2-(piperidin-1-yl)ethyl]benzamide monohydrate

B K Revathi ^a, D Reuben Jonathan ^b, S Sathya ^a, K Prathebha ^a, G Usha ^a,^*

PMCID: PMC4420061 PMID: 25995948

Abstract

In the title compound, C₁₅H₂₂N₂O·H₂O, the dihedral angle between the planes of the piperidine and benzene rings is 31.63 (1)°. The piperidine ring adopts a chair conformation. The water solvent molecule is involved in interspecies O—H⋯O, O—H⋯N, N—H⋯O and weak C—H⋯O hydrogen-bonding interactions, giving rise to chains extending along [010].

Keywords: crystal structure, piperidine, benzamide, hydrogen bonding

Related literature

For the biological activity of piperidine and benzamide derivatives, see: Ramalingan et al. (2004 ▸); Sargent & May (1970 ▸); Magar et al. (2010 ▸); Fun et al. (2011 ▸); Haffner et al. (2010 ▸); Lavanya et al. (2010 ▸). For related structures, see: Ávila et al. (2010 ▸); Prathebha et al. (2014 ▸, 2015 ▸); Al-abbasi et al. (2010 ▸). For the synthesis, see: Prathebha et al. (2014 ▸, 2015 ▸). graphic file with name e-71-0o359-scheme1.jpg

Experimental

Crystal data

C₁₅H₂₂N₂O·H₂O
M _r = 264.36
Monoclinic,
a = 14.8504 (17) Å
b = 6.8243 (6) Å
c = 15.0070 (18) Å
β = 98.653 (4)°
V = 1503.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T _min = 0.980, T _max = 0.986
25938 measured reflections
3735 independent reflections
2311 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.203
S = 1.11
3688 reflections
181 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 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: SHELXS97 (Sheldrick, 2008 ▸); 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/S2056989015007653/zs2330sup1.cif

e-71-0o359-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007653/zs2330Isup2.hkl

e-71-0o359-Isup2.hkl^{(177.2KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015007653/zs2330Isup3.cml

Click here for additional data file.^{(1,022.8KB, tif)}

. DOI: 10.1107/S2056989015007653/zs2330fig1.tif

The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.^{(1.8MB, tif)}

. DOI: 10.1107/S2056989015007653/zs2330fig2.tif

The packing of the molecules in the crystal structure. The dashed lines indicate hydrogen bonds.

CCDC reference: 1054604

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1WH1WO1ⁱ	0.85(2)	1.99(2)	2.840(2)	177(3)
O1WH2WN1ⁱⁱ	0.85(2)	2.04(2)	2.883(3)	177(3)
N2H2O1W	0.86	2.11	2.906(2)	153
C7H7AO1W ⁱⁱⁱ	0.97	2.55	3.472(3)	159
C10H10O1W	0.93	2.51	3.374(3)	154

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

Acknowledgments

The authors thank SAIF, IIT, Madras, for access to the X-ray data-collection facility.

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). Benzamides have been reported to correlate with many pharmacological processes such as anti-emetic, anti-psychotic and anti-arrythmic activities. Various N-substituted derivatives of benzamide are reported to possess anti-convulsant activity (Magar et al., 2010; Fun et al., 2011). Recently, Haffner & Ulrich (2010) reported that some N-substituted derivatives of benzamide can block the Kv1.3 ion channel. Moreover, these have been scanned for anti-microbial and anti-oxidant activities (Lavanya et al., 2010).

The substituted benzamide derivative, the title compound, C₁₅H₂₄N₂O₂, has been prepared and the structure is reported herein. In this compound (Fig. 1) the dihedral angle between piperidine ring the and the benzene ring ring is 31.63 (1)°. The C—C, C—N and C═O bond lengths and C—C—C and C—N—C bond angles are in the normal range and are comparable with literature values and are also in good agreement with the values in similar reported structure (Avila et al., 2010, Prathebha et al., 2014). The C═O distance [1.231 (2) Å] is comparable with a previously reported value (Al-abbasi et al., 2010)·. The bond angle sum around N1 [330.45 (2)°], shows sp³ hybridization of the atom. The piperidine ring adopts a chair conformation with puckering parameters of q2 = 0.035 (3) Å, φ2 = 182 (5)° q3 = -0.564 (3) Å, QT = 0.565 (3)0143 (2) Å and θ2 = 176.9 (3)°.

The water molecule is involved in the formation of inter-species hydrogen-bonding interactions (Table 1), acting as both a double donor (O1W—H···Oⁱ and O1W—H···N1ⁱⁱ) as well as an acceptor (N2—H···O1W. One-dimensional chains are generated, extending along [010] (Fig. 2). Weak C—H···OW hydrogen bonds are also present.

S2. Experimental

The title compound was synthesized following a published procedure (Prathebha et al., 2014, 2015). In a 250 ml round-bottomed flask, 120 ml of ethylmethylketone was added to 1,2-aminoethylpiperidine (0.02 mol) and stirred at room temperature. After 5 min, triethylamine (0.04 mol) was added and the mixture was stirred for 15 min. 4-Methylbenzoyl chloride (0.04 mol) was then added and the reaction mixture was stirred at room temperature for 2 hr. A white precipitate of triethylammonium chloride was formed, which was filtered and the filtrate was evaporated to give the crude product. Two recrystallizations from ethylmethylketone give colourless block-like crystals of the title compound (yield: 82%).