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

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

doi:10.1107/S2056989014026851

. 2015 Jan 1;71(Pt 1):o39–o40. doi: 10.1107/S2056989014026851

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

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

PMCID: PMC4331843 PMID: 25705496

Abstract

In the title compound, C₁₄H₁₉ClN₂O₂·H₂O, the piperdine ring adopts a chair conformation. The dihedral angle between the mean plane of the piperidine ring and that of the phenyl ring is 41.64 (1)°. In the crystal, molecules are linked by O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds involving the water molecule, forming double-stranded chains propagating along [010].

Keywords: crystal structure, piperidine, benzamide, monohydrate, hydrogen bonding

Related literature

For the synthesis of the title compound, see: Prathebha et al. (2013 ▸, 2014 ▸). For the biological activities of piperdine derivatives, see: Pandey & Chawla (2012 ▸); Jayalakshmi & Nanjundan (2008 ▸); Parthiban et al. (2005 ▸); Aridoss et al. (2008 ▸); Ramachandran et al. (2011 ▸). For related structures, see: Prathebha et al. (2014 ▸); Ávila et al. (2010 ▸); Al-abbasi et al. (2010 ▸). graphic file with name e-71-00o39-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₉ClN₂O·H₂O
M _r = 284.78
Monoclinic,
a = 14.9115 (6) Å
b = 6.6899 (3) Å
c = 15.6215 (7) Å
β = 102.956 (2)°
V = 1518.67 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T _min = 0.939, T _max = 0.951
12566 measured reflections
3780 independent reflections
1953 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.160
S = 1.01
3780 reflections
181 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: XPREP in SAINT; 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, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014026851/su5034sup1.cif

e-71-00o39-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026851/su5034Isup2.hkl

e-71-00o39-Isup2.hkl^{(179.5KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014026851/su5034Isup3.cml

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

. DOI: 10.1107/S2056989014026851/su5034fig1.tif

The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.^{(2.1MB, tif)}

b . DOI: 10.1107/S2056989014026851/su5034fig2.tif

A view along the b axis of the crystal packing of the title compound. The dashed lines indicate the hydrogen bonds (see Table 1 for details; C-bound H atoms have been omitted for clarity).

CCDC reference: 1038084

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1WH1WAN1ⁱ	0.83(2)	2.03(2)	2.851(3)	174(2)
N2H2O1W	0.86	2.06	2.855(2)	153
C6H6BO1W	0.97	2.59	3.406(3)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

S1. Comment

The piperidine derivatives were reported to have antimicrobial activity. Piperidine derivatives have been synthesized for pharmaceutical research as they are very efficient against resistance microorganisms. The substituted piperidine derivatives were also reported to have antimicrobial activity (Pandey & Chawla, 2012; Jayalakshmi & Nanjundan, 2008; Parthiban et al., 2005; Aridoss et al., 2008; Ramachandran et al. 2011).

In the title compound, Fig. 1, the piperidine ring is cis to the phenyl ring. The C—N distances [1.335 (2) - 1.464 (2) Å] are in the normal range and are in good agreement with values of from similar structures (Ávila et al., 2010; Prathebha et al., 2014). The bond angle sum around atoms N1 and N2 [333.2 (4)° and 359.97 (1)°, respectively] shows sp³ hybridization. The C═O distance [1.231 (2) Å] is comparable with the value reported previously (Al-abbasi et al., 2010). The piperdine ring adopts a chair conformation with puckering parameters of q2 = 0.6994 (0) Å, φ2 = 88.60 (0)° q3 = -0.0267 (0) Å, QT = 0.6999 Å and θ2 = 92.19 (2)°.

In the crystal, adjacent molecules are linked by O-H···N, O-H···O and C-H···O hydrogen bonds, involving the water molecule, forming double stranded chains propagating along [010]; see Table 1 and Fig. 2

S2. Experimental

The title compound was synthesized following a publish procedure (Prathebha et al., 2013, 2014). 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. Then 4-chlorobenzoylchloride (0.04 mol) was added and the reaction mixture was stirred at room temperature for ca. 2 h. A white precipitate of triethylammoniumchloride was formed. It was filtered and the filtrate was evaporated to give the crude product. It was recrystallized twice from ethylmethylketone (yield: 82%) giving colourless block-like crystals of the title compound.