organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(4-Chloro­phen­yl)-4-methyl­piperidine-1-carboxamide

aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: liyufeng8111@163.com

(Received 31 May 2011; accepted 20 June 2011; online 25 June 2011)

In the title compound, C13H17ClN2O, the piperidine ring adopts a chair conformation and the N atom in that ring is close to pyramidal (bond angle sum = 357.5°). In the crystal, mol­ecules are linked into C(4) chains propagating in [010] by N—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Köhn et al. (2004[Köhn, U., Günther, W., Görls, H. & Anders, E. (2004). Tetrahedron Asymmetry, 15, 1419-1426.]).

[Scheme 1]

Experimental

Crystal data
  • C13H17ClN2O

  • Mr = 252.74

  • Monoclinic, P 21 /c

  • a = 13.286 (3) Å

  • b = 9.1468 (18) Å

  • c = 10.957 (2) Å

  • β = 95.36 (3)°

  • V = 1325.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 293 K

  • 0.22 × 0.21 × 0.19 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 12608 measured reflections

  • 3038 independent reflections

  • 1999 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.154

  • S = 1.13

  • 3038 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O1i 0.86 2.33 2.940 (2) 128
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The crystal structure of the title compound, (I), is presented herein (Fig. 1). The six-membered rings (N1,C2, C3, C4, C5, C6) are in chair conformations. The molecules are linked into [010] chains by way of alternating N—H···O hydrogen bond linkages. The structure of a related compound has already been determined (Köhn et al., 2004).

Related literature top

For a related structure, see: Köhn et al. (2004).

Experimental top

A mixture of 4-methylpiperidine (0.1 mol), and (4-chlorophenyl)carbamic chloride (0.1 mol) was stirred in refluxing ethanol (20 ml) for 4 h to afford the title compound (0.075 mol, yield 75%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Refinement top

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93–0.97 Å; N—H = 0.86Å and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.
N-(4-Chlorophenyl)-4-methylpiperidine-1-carboxamide top
Crystal data top
C13H17ClN2OF(000) = 536
Mr = 252.74Dx = 1.266 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.286 (3) ÅCell parameters from 1999 reflections
b = 9.1468 (18) Åθ = 3.0–27.3°
c = 10.957 (2) ŵ = 0.28 mm1
β = 95.36 (3)°T = 293 K
V = 1325.7 (5) Å3Bar, colorless
Z = 40.22 × 0.21 × 0.19 mm
Data collection top
Bruker SMART CCD
diffractometer
1999 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 1717
12608 measured reflectionsk = 1011
3038 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0806P)2 + 0.0785P]
where P = (Fo2 + 2Fc2)/3
3038 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C13H17ClN2OV = 1325.7 (5) Å3
Mr = 252.74Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.286 (3) ŵ = 0.28 mm1
b = 9.1468 (18) ÅT = 293 K
c = 10.957 (2) Å0.22 × 0.21 × 0.19 mm
β = 95.36 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1999 reflections with I > 2σ(I)
12608 measured reflectionsRint = 0.037
3038 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.13Δρmax = 0.34 e Å3
3038 reflectionsΔρmin = 0.37 e Å3
154 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.83830 (4)0.11364 (7)0.42550 (6)0.0690 (2)
O10.44390 (10)0.14454 (13)0.73592 (13)0.0484 (4)
C80.57283 (13)0.30099 (18)0.59955 (16)0.0379 (4)
N20.49079 (11)0.36204 (15)0.65583 (15)0.0432 (4)
H2A0.47930.45430.64910.052*
C120.63981 (15)0.1297 (2)0.46199 (18)0.0452 (5)
H12A0.63040.05260.40670.054*
C130.55876 (14)0.1876 (2)0.51610 (17)0.0436 (4)
H13A0.49430.15000.49630.052*
N10.35363 (11)0.34976 (16)0.77039 (16)0.0447 (4)
C90.66864 (14)0.35849 (19)0.62681 (18)0.0421 (4)
H9A0.67830.43560.68200.051*
C110.73497 (14)0.1877 (2)0.49098 (17)0.0436 (4)
C70.42888 (13)0.27715 (18)0.72121 (16)0.0385 (4)
C100.75036 (14)0.3019 (2)0.57244 (17)0.0447 (4)
H10A0.81470.34060.59080.054*
C60.30658 (13)0.48409 (19)0.71993 (19)0.0473 (5)
H6A0.34790.52580.66030.057*
H6B0.30210.55490.78510.057*
C20.29344 (15)0.2735 (2)0.85563 (19)0.0485 (5)
H2B0.28640.33520.92640.058*
H2C0.32810.18470.88400.058*
C40.13554 (16)0.3713 (3)0.7433 (2)0.0639 (6)
H4A0.12440.43630.81190.077*
C50.20188 (15)0.4518 (3)0.6593 (2)0.0567 (5)
H5A0.20790.39310.58660.068*
H5B0.16940.54310.63350.068*
C30.19038 (16)0.2355 (3)0.7956 (2)0.0587 (6)
H3A0.15080.19020.85540.070*
H3B0.19710.16570.73020.070*
C10.0326 (2)0.3348 (5)0.6765 (4)0.1222 (14)
H1A0.00040.42310.64590.183*
H1B0.00880.28810.73230.183*
H1C0.04150.27010.60940.183*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0609 (4)0.0796 (5)0.0696 (4)0.0091 (3)0.0222 (3)0.0124 (3)
O10.0568 (8)0.0314 (6)0.0577 (8)0.0031 (6)0.0080 (7)0.0042 (6)
C80.0391 (9)0.0341 (9)0.0402 (9)0.0000 (7)0.0026 (7)0.0040 (7)
N20.0428 (8)0.0294 (7)0.0585 (10)0.0012 (6)0.0104 (7)0.0010 (7)
C120.0547 (11)0.0415 (10)0.0392 (10)0.0005 (8)0.0029 (9)0.0049 (8)
C130.0443 (10)0.0431 (10)0.0418 (10)0.0047 (8)0.0034 (8)0.0020 (8)
N10.0400 (8)0.0375 (8)0.0575 (10)0.0021 (6)0.0089 (7)0.0060 (7)
C90.0454 (10)0.0371 (9)0.0439 (10)0.0064 (8)0.0044 (8)0.0028 (8)
C110.0473 (10)0.0453 (10)0.0389 (9)0.0021 (8)0.0082 (8)0.0028 (8)
C70.0400 (9)0.0340 (9)0.0406 (9)0.0016 (7)0.0002 (8)0.0005 (7)
C100.0406 (9)0.0485 (11)0.0453 (10)0.0060 (8)0.0053 (8)0.0011 (8)
C60.0474 (10)0.0351 (9)0.0600 (12)0.0049 (8)0.0080 (9)0.0012 (8)
C20.0516 (11)0.0455 (10)0.0496 (11)0.0007 (9)0.0109 (9)0.0035 (9)
C40.0430 (11)0.0858 (17)0.0633 (14)0.0028 (11)0.0065 (10)0.0013 (12)
C50.0482 (11)0.0655 (13)0.0561 (12)0.0051 (10)0.0030 (10)0.0064 (11)
C30.0559 (12)0.0610 (13)0.0609 (13)0.0165 (10)0.0141 (10)0.0005 (10)
C10.0510 (15)0.184 (4)0.128 (3)0.027 (2)0.0114 (18)0.031 (3)
Geometric parameters (Å, º) top
Cl1—C111.7441 (19)C6—C51.514 (3)
O1—C71.237 (2)C6—H6A0.9700
C8—C91.384 (2)C6—H6B0.9700
C8—C131.384 (2)C2—C31.503 (3)
C8—N21.416 (2)C2—H2B0.9700
N2—C71.379 (2)C2—H2C0.9700
N2—H2A0.8600C4—C51.522 (3)
C12—C111.381 (3)C4—C31.524 (3)
C12—C131.382 (3)C4—C11.526 (3)
C12—H12A0.9300C4—H4A0.9800
C13—H13A0.9300C5—H5A0.9700
N1—C71.353 (2)C5—H5B0.9700
N1—C21.462 (2)C3—H3A0.9700
N1—C61.463 (2)C3—H3B0.9700
C9—C101.386 (3)C1—H1A0.9600
C9—H9A0.9300C1—H1B0.9600
C11—C101.377 (3)C1—H1C0.9600
C10—H10A0.9300
C9—C8—C13119.49 (16)H6A—C6—H6B108.1
C9—C8—N2119.08 (16)N1—C2—C3111.16 (17)
C13—C8—N2121.42 (16)N1—C2—H2B109.4
C7—N2—C8121.65 (14)C3—C2—H2B109.4
C7—N2—H2A119.2N1—C2—H2C109.4
C8—N2—H2A119.2C3—C2—H2C109.4
C11—C12—C13119.19 (17)H2B—C2—H2C108.0
C11—C12—H12A120.4C5—C4—C3109.76 (18)
C13—C12—H12A120.4C5—C4—C1111.1 (2)
C12—C13—C8120.52 (17)C3—C4—C1112.2 (2)
C12—C13—H13A119.7C5—C4—H4A107.9
C8—C13—H13A119.7C3—C4—H4A107.9
C7—N1—C2119.25 (15)C1—C4—H4A107.9
C7—N1—C6124.54 (16)C6—C5—C4112.92 (18)
C2—N1—C6113.70 (15)C6—C5—H5A109.0
C8—C9—C10120.46 (17)C4—C5—H5A109.0
C8—C9—H9A119.8C6—C5—H5B109.0
C10—C9—H9A119.8C4—C5—H5B109.0
C10—C11—C12121.20 (17)H5A—C5—H5B107.8
C10—C11—Cl1119.10 (15)C2—C3—C4111.12 (19)
C12—C11—Cl1119.69 (14)C2—C3—H3A109.4
O1—C7—N1123.05 (16)C4—C3—H3A109.4
O1—C7—N2121.51 (16)C2—C3—H3B109.4
N1—C7—N2115.41 (15)C4—C3—H3B109.4
C11—C10—C9119.13 (17)H3A—C3—H3B108.0
C11—C10—H10A120.4C4—C1—H1A109.5
C9—C10—H10A120.4C4—C1—H1B109.5
N1—C6—C5110.16 (16)H1A—C1—H1B109.5
N1—C6—H6A109.6C4—C1—H1C109.5
C5—C6—H6A109.6H1A—C1—H1C109.5
N1—C6—H6B109.6H1B—C1—H1C109.5
C5—C6—H6B109.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.332.940 (2)128
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H17ClN2O
Mr252.74
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.286 (3), 9.1468 (18), 10.957 (2)
β (°) 95.36 (3)
V3)1325.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.22 × 0.21 × 0.19
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12608, 3038, 1999
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.154, 1.13
No. of reflections3038
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.37

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.332.940 (2)128
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKöhn, U., Günther, W., Görls, H. & Anders, E. (2004). Tetrahedron Asymmetry, 15, 1419–1426.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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