organic compounds
N-[2-(piperidin-1-yl)ethyl]benzamide monohydrate
of 4-methyl-aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Chemistry, Madras Christian College, Chennai-59, India
*Correspondence e-mail: guqmc@yahoo.com
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.
CCDC reference: 1054604
1. 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).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
CCDC reference: 1054604
https://doi.org/10.1107/S2056989015007653/zs2330sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007653/zs2330Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015007653/zs2330Isup3.cml
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%).
Hydrogen atoms were positioned geometrically and treated as riding on their parent atoms and water H-atoms were located from difference Fourier maps and refined with C—H distance of 0.93–0.97 Å, an O—H distance of 0.85 (2) Å and an N—H distance of 0.86 Å, with Uiso(H) = 1.5 Ueq(C-methyl), 1.5Ueq(O) and 1.2Ueq(C) for other H atoms. One reflection (100) was considered to be affected by the beamstop.
Biologically active
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 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.
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: Avila et al. (2010); Prathebha et al. (2014, 2015); Al-abbasi et al. (2010). For the synthesis, see: Prathebha et al. (2014, 2015).
Data collection: APEX2 (Bruker, 2004); cell
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 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate hydrogen bonds. |
C15H22N2O·H2O | F(000) = 576 |
Mr = 264.36 | Dx = 1.168 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.8504 (17) Å | θ = 1.4–28.3° |
b = 6.8243 (6) Å | µ = 0.08 mm−1 |
c = 15.0070 (18) Å | T = 293 K |
β = 98.653 (4)° | Block, colourless |
V = 1503.6 (3) Å3 | 0.24 × 0.22 × 0.22 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3735 independent reflections |
Radiation source: fine-focus sealed tube | 2311 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and φ scans | θmax = 28.3°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −19→19 |
Tmin = 0.980, Tmax = 0.986 | k = −9→9 |
25938 measured reflections | l = −19→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.203 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0894P)2 + 0.5035P] where P = (Fo2 + 2Fc2)/3 |
3688 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.34 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
C15H22N2O·H2O | V = 1503.6 (3) Å3 |
Mr = 264.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.8504 (17) Å | µ = 0.08 mm−1 |
b = 6.8243 (6) Å | T = 293 K |
c = 15.0070 (18) Å | 0.24 × 0.22 × 0.22 mm |
β = 98.653 (4)° |
Bruker Kappa APEXII CCD diffractometer | 3735 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2311 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.986 | Rint = 0.031 |
25938 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 3 restraints |
wR(F2) = 0.203 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.34 e Å−3 |
3688 reflections | Δρmin = −0.22 e Å−3 |
181 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.38752 (16) | 0.4342 (3) | 0.07521 (17) | 0.0542 (6) | |
H1A | 0.3939 | 0.4274 | 0.0119 | 0.065* | |
H1B | 0.4338 | 0.5227 | 0.1046 | 0.065* | |
C2 | 0.29416 (17) | 0.5141 (4) | 0.08428 (19) | 0.0636 (7) | |
H2A | 0.2896 | 0.5320 | 0.1476 | 0.076* | |
H2B | 0.2861 | 0.6408 | 0.0549 | 0.076* | |
C3 | 0.22041 (17) | 0.3770 (4) | 0.04252 (19) | 0.0665 (7) | |
H3A | 0.1619 | 0.4229 | 0.0553 | 0.080* | |
H3B | 0.2186 | 0.3751 | −0.0224 | 0.080* | |
C4 | 0.23786 (17) | 0.1739 (4) | 0.0794 (2) | 0.0657 (7) | |
H4A | 0.2303 | 0.1724 | 0.1425 | 0.079* | |
H4B | 0.1936 | 0.0845 | 0.0473 | 0.079* | |
C5 | 0.33188 (17) | 0.1055 (4) | 0.0704 (2) | 0.0635 (7) | |
H5A | 0.3415 | −0.0241 | 0.0966 | 0.076* | |
H5B | 0.3377 | 0.0961 | 0.0070 | 0.076* | |
C6 | 0.49185 (15) | 0.1599 (4) | 0.10743 (17) | 0.0541 (6) | |
H6A | 0.5052 | 0.1855 | 0.0472 | 0.065* | |
H6B | 0.4909 | 0.0190 | 0.1156 | 0.065* | |
C7 | 0.56594 (14) | 0.2458 (4) | 0.17469 (18) | 0.0558 (6) | |
H7A | 0.5700 | 0.3857 | 0.1646 | 0.067* | |
H7B | 0.5519 | 0.2259 | 0.2351 | 0.067* | |
C8 | 0.72909 (13) | 0.2522 (3) | 0.16379 (13) | 0.0409 (5) | |
C9 | 0.81183 (13) | 0.1325 (3) | 0.15644 (13) | 0.0386 (4) | |
C10 | 0.82043 (14) | −0.0617 (3) | 0.18282 (15) | 0.0471 (5) | |
H10 | 0.7727 | −0.1231 | 0.2054 | 0.057* | |
C11 | 0.89864 (15) | −0.1651 (3) | 0.17615 (16) | 0.0517 (6) | |
H11 | 0.9028 | −0.2954 | 0.1945 | 0.062* | |
C12 | 0.97060 (14) | −0.0808 (4) | 0.14315 (14) | 0.0500 (5) | |
C13 | 0.96249 (15) | 0.1133 (4) | 0.11755 (16) | 0.0553 (6) | |
H13 | 1.0104 | 0.1739 | 0.0949 | 0.066* | |
C14 | 0.88495 (15) | 0.2194 (3) | 0.12477 (15) | 0.0500 (5) | |
H14 | 0.8818 | 0.3509 | 0.1082 | 0.060* | |
C15 | 1.05545 (18) | −0.1956 (5) | 0.1353 (2) | 0.0762 (8) | |
H15A | 1.0492 | −0.3265 | 0.1571 | 0.114* | |
H15B | 1.1069 | −0.1334 | 0.1706 | 0.114* | |
H15C | 1.0645 | −0.2002 | 0.0734 | 0.114* | |
N1 | 0.40171 (11) | 0.2394 (2) | 0.11529 (12) | 0.0452 (4) | |
N2 | 0.65238 (11) | 0.1538 (3) | 0.16645 (13) | 0.0497 (5) | |
H2 | 0.6540 | 0.0281 | 0.1631 | 0.060* | |
O1 | 0.73327 (11) | 0.4323 (2) | 0.16610 (13) | 0.0613 (5) | |
O1W | 0.61401 (11) | −0.2569 (2) | 0.19557 (13) | 0.0553 (5) | |
H1W | 0.6502 (18) | −0.350 (4) | 0.189 (2) | 0.090 (10)* | |
H2W | 0.611 (2) | −0.259 (5) | 0.2514 (13) | 0.116 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0519 (13) | 0.0525 (13) | 0.0580 (13) | −0.0099 (10) | 0.0078 (10) | 0.0021 (10) |
C2 | 0.0657 (16) | 0.0500 (13) | 0.0732 (16) | 0.0106 (12) | 0.0042 (12) | 0.0045 (12) |
C3 | 0.0461 (14) | 0.0774 (17) | 0.0734 (17) | 0.0080 (12) | 0.0002 (11) | −0.0027 (14) |
C4 | 0.0479 (14) | 0.0703 (16) | 0.0779 (17) | −0.0168 (12) | 0.0061 (12) | −0.0064 (14) |
C5 | 0.0588 (15) | 0.0482 (13) | 0.0813 (18) | −0.0057 (11) | 0.0028 (12) | −0.0127 (12) |
C6 | 0.0449 (12) | 0.0551 (13) | 0.0632 (14) | 0.0039 (10) | 0.0108 (10) | −0.0128 (11) |
C7 | 0.0366 (11) | 0.0558 (13) | 0.0760 (16) | 0.0008 (10) | 0.0114 (10) | −0.0201 (12) |
C8 | 0.0398 (11) | 0.0414 (10) | 0.0423 (10) | 0.0025 (8) | 0.0088 (8) | 0.0009 (8) |
C9 | 0.0353 (10) | 0.0412 (10) | 0.0400 (10) | −0.0013 (8) | 0.0078 (8) | −0.0015 (8) |
C10 | 0.0385 (11) | 0.0454 (11) | 0.0584 (13) | −0.0032 (9) | 0.0107 (9) | 0.0045 (9) |
C11 | 0.0467 (12) | 0.0446 (12) | 0.0631 (14) | 0.0061 (10) | 0.0059 (10) | 0.0037 (10) |
C12 | 0.0396 (11) | 0.0662 (14) | 0.0441 (11) | 0.0117 (10) | 0.0060 (9) | 0.0054 (10) |
C13 | 0.0383 (11) | 0.0726 (15) | 0.0579 (13) | 0.0011 (10) | 0.0164 (9) | 0.0152 (11) |
C14 | 0.0462 (12) | 0.0475 (11) | 0.0581 (13) | −0.0004 (10) | 0.0140 (10) | 0.0111 (10) |
C15 | 0.0564 (16) | 0.103 (2) | 0.0723 (17) | 0.0339 (15) | 0.0197 (13) | 0.0177 (16) |
N1 | 0.0375 (9) | 0.0439 (9) | 0.0546 (10) | 0.0010 (7) | 0.0085 (7) | −0.0041 (8) |
N2 | 0.0355 (9) | 0.0418 (9) | 0.0729 (12) | 0.0023 (7) | 0.0118 (8) | −0.0075 (9) |
O1 | 0.0545 (10) | 0.0403 (8) | 0.0941 (13) | 0.0015 (7) | 0.0270 (9) | −0.0002 (8) |
O1W | 0.0542 (10) | 0.0416 (9) | 0.0731 (13) | 0.0003 (7) | 0.0194 (8) | −0.0004 (8) |
C1—N1 | 1.461 (3) | C7—H7B | 0.9700 |
C1—C2 | 1.515 (3) | C8—O1 | 1.231 (2) |
C1—H1A | 0.9700 | C8—N2 | 1.328 (3) |
C1—H1B | 0.9700 | C8—C9 | 1.493 (3) |
C2—C3 | 1.504 (4) | C9—C14 | 1.383 (3) |
C2—H2A | 0.9700 | C9—C10 | 1.383 (3) |
C2—H2B | 0.9700 | C10—C11 | 1.376 (3) |
C3—C4 | 1.501 (4) | C10—H10 | 0.9300 |
C3—H3A | 0.9700 | C11—C12 | 1.370 (3) |
C3—H3B | 0.9700 | C11—H11 | 0.9300 |
C4—C5 | 1.498 (3) | C12—C13 | 1.379 (3) |
C4—H4A | 0.9700 | C12—C15 | 1.503 (3) |
C4—H4B | 0.9700 | C13—C14 | 1.378 (3) |
C5—N1 | 1.468 (3) | C13—H13 | 0.9300 |
C5—H5A | 0.9700 | C14—H14 | 0.9300 |
C5—H5B | 0.9700 | C15—H15A | 0.9600 |
C6—N1 | 1.465 (3) | C15—H15B | 0.9600 |
C6—C7 | 1.496 (3) | C15—H15C | 0.9600 |
C6—H6A | 0.9700 | N2—H2 | 0.8600 |
C6—H6B | 0.9700 | O1W—H1W | 0.849 (17) |
C7—N2 | 1.451 (3) | O1W—H2W | 0.845 (18) |
C7—H7A | 0.9700 | ||
N1—C1—C2 | 111.57 (19) | C6—C7—H7A | 109.6 |
N1—C1—H1A | 109.3 | N2—C7—H7B | 109.6 |
C2—C1—H1A | 109.3 | C6—C7—H7B | 109.6 |
N1—C1—H1B | 109.3 | H7A—C7—H7B | 108.2 |
C2—C1—H1B | 109.3 | O1—C8—N2 | 122.92 (18) |
H1A—C1—H1B | 108.0 | O1—C8—C9 | 120.65 (18) |
C3—C2—C1 | 111.0 (2) | N2—C8—C9 | 116.43 (17) |
C3—C2—H2A | 109.4 | C14—C9—C10 | 117.78 (18) |
C1—C2—H2A | 109.4 | C14—C9—C8 | 119.21 (18) |
C3—C2—H2B | 109.4 | C10—C9—C8 | 122.98 (17) |
C1—C2—H2B | 109.4 | C11—C10—C9 | 120.89 (19) |
H2A—C2—H2B | 108.0 | C11—C10—H10 | 119.6 |
C4—C3—C2 | 110.3 (2) | C9—C10—H10 | 119.6 |
C4—C3—H3A | 109.6 | C12—C11—C10 | 121.6 (2) |
C2—C3—H3A | 109.6 | C12—C11—H11 | 119.2 |
C4—C3—H3B | 109.6 | C10—C11—H11 | 119.2 |
C2—C3—H3B | 109.6 | C11—C12—C13 | 117.63 (19) |
H3A—C3—H3B | 108.1 | C11—C12—C15 | 121.2 (2) |
C5—C4—C3 | 111.5 (2) | C13—C12—C15 | 121.2 (2) |
C5—C4—H4A | 109.3 | C14—C13—C12 | 121.4 (2) |
C3—C4—H4A | 109.3 | C14—C13—H13 | 119.3 |
C5—C4—H4B | 109.3 | C12—C13—H13 | 119.3 |
C3—C4—H4B | 109.3 | C13—C14—C9 | 120.7 (2) |
H4A—C4—H4B | 108.0 | C13—C14—H14 | 119.7 |
N1—C5—C4 | 111.6 (2) | C9—C14—H14 | 119.7 |
N1—C5—H5A | 109.3 | C12—C15—H15A | 109.5 |
C4—C5—H5A | 109.3 | C12—C15—H15B | 109.5 |
N1—C5—H5B | 109.3 | H15A—C15—H15B | 109.5 |
C4—C5—H5B | 109.3 | C12—C15—H15C | 109.5 |
H5A—C5—H5B | 108.0 | H15A—C15—H15C | 109.5 |
N1—C6—C7 | 112.87 (18) | H15B—C15—H15C | 109.5 |
N1—C6—H6A | 109.0 | C1—N1—C6 | 112.36 (18) |
C7—C6—H6A | 109.0 | C1—N1—C5 | 109.23 (18) |
N1—C6—H6B | 109.0 | C6—N1—C5 | 108.86 (17) |
C7—C6—H6B | 109.0 | C8—N2—C7 | 123.92 (18) |
H6A—C6—H6B | 107.8 | C8—N2—H2 | 118.0 |
N2—C7—C6 | 110.08 (18) | C7—N2—H2 | 118.0 |
N2—C7—H7A | 109.6 | H1W—O1W—H2W | 103 (2) |
N1—C1—C2—C3 | −56.8 (3) | C11—C12—C13—C14 | 0.0 (3) |
C1—C2—C3—C4 | 52.5 (3) | C15—C12—C13—C14 | −179.8 (2) |
C2—C3—C4—C5 | −53.0 (3) | C12—C13—C14—C9 | −1.3 (4) |
C3—C4—C5—N1 | 57.1 (3) | C10—C9—C14—C13 | 1.8 (3) |
N1—C6—C7—N2 | 177.01 (19) | C8—C9—C14—C13 | 179.7 (2) |
O1—C8—C9—C14 | −19.8 (3) | C2—C1—N1—C6 | −179.81 (19) |
N2—C8—C9—C14 | 159.4 (2) | C2—C1—N1—C5 | 59.3 (3) |
O1—C8—C9—C10 | 157.9 (2) | C7—C6—N1—C1 | 77.8 (3) |
N2—C8—C9—C10 | −22.9 (3) | C7—C6—N1—C5 | −161.1 (2) |
C14—C9—C10—C11 | −1.1 (3) | C4—C5—N1—C1 | −59.5 (3) |
C8—C9—C10—C11 | −178.91 (19) | C4—C5—N1—C6 | 177.5 (2) |
C9—C10—C11—C12 | −0.1 (3) | O1—C8—N2—C7 | −1.7 (3) |
C10—C11—C12—C13 | 0.7 (3) | C9—C8—N2—C7 | 179.16 (19) |
C10—C11—C12—C15 | −179.4 (2) | C6—C7—N2—C8 | 133.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1i | 0.85 (2) | 1.99 (2) | 2.840 (2) | 177 (3) |
O1W—H2W···N1ii | 0.85 (2) | 2.04 (2) | 2.883 (3) | 177 (3) |
N2—H2···O1W | 0.86 | 2.11 | 2.906 (2) | 153 |
C7—H7A···O1Wiii | 0.97 | 2.55 | 3.472 (3) | 159 |
C7—H7A···O1 | 0.97 | 2.44 | 2.812 (3) | 102 |
C10—H10···O1W | 0.93 | 2.51 | 3.374 (3) | 154 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1i | 0.849 (17) | 1.992 (17) | 2.840 (2) | 177 (3) |
O1W—H2W···N1ii | 0.845 (18) | 2.039 (18) | 2.883 (3) | 177 (3) |
N2—H2···O1W | 0.86 | 2.11 | 2.906 (2) | 153 |
C7—H7A···O1Wiii | 0.97 | 2.55 | 3.472 (3) | 159 |
C10—H10···O1W | 0.93 | 2.51 | 3.374 (3) | 154 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z. |
Acknowledgements
The authors thank SAIF, IIT, Madras, for access to the X-ray data-collection facility.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.