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

Li, Y.-F.

doi:10.1107/S1600536811024123

organic compounds

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Volume 67| Part 7| July 2011| Page o1796

doi:10.1107/S1600536811024123

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

Yu-Feng Li ^a ^*

^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 ).

Experimental

Crystal data

C₁₃H₁₇ClN₂O
M_r = 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)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.154
S = 1.13
3038 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024123/hb5902sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024123/hb5902Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024123/hb5902Isup3.cml

checkCIF report

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.

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

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.

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

Crystal data top

C₁₃H₁₇ClN₂O	F(000) = 536
M_r = 252.74	D_x = 1.266 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.286 (3) Å	Cell parameters from 1999 reflections
b = 9.1468 (18) Å	θ = 3.0–27.3°
c = 10.957 (2) Å	µ = 0.28 mm⁻¹
β = 95.36 (3)°	T = 293 K
V = 1325.7 (5) Å³	Bar, colorless
Z = 4	0.22 × 0.21 × 0.19 mm

Data collection top

Bruker SMART CCD diffractometer	1999 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −17→17
12608 measured reflections	k = −10→11
3038 independent reflections	l = −14→14

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0806P)² + 0.0785P] where P = (F_o² + 2F_c²)/3
3038 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₃H₁₇ClN₂O	V = 1325.7 (5) Å³
M_r = 252.74	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.286 (3) Å	µ = 0.28 mm⁻¹
b = 9.1468 (18) Å	T = 293 K
c = 10.957 (2) Å	0.22 × 0.21 × 0.19 mm
β = 95.36 (3)°

Data collection top

Bruker SMART CCD diffractometer	1999 reflections with I > 2σ(I)
12608 measured reflections	R_int = 0.037
3038 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.13	Δρ_max = 0.34 e Å⁻³
3038 reflections	Δρ_min = −0.37 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.83830 (4)	0.11364 (7)	0.42550 (6)	0.0690 (2)
O1	0.44390 (10)	0.14454 (13)	0.73592 (13)	0.0484 (4)
C8	0.57283 (13)	0.30099 (18)	0.59955 (16)	0.0379 (4)
N2	0.49079 (11)	0.36204 (15)	0.65583 (15)	0.0432 (4)
H2A	0.4793	0.4543	0.6491	0.052*
C12	0.63981 (15)	0.1297 (2)	0.46199 (18)	0.0452 (5)
H12A	0.6304	0.0526	0.4067	0.054*
C13	0.55876 (14)	0.1876 (2)	0.51610 (17)	0.0436 (4)
H13A	0.4943	0.1500	0.4963	0.052*
N1	0.35363 (11)	0.34976 (16)	0.77039 (16)	0.0447 (4)
C9	0.66864 (14)	0.35849 (19)	0.62681 (18)	0.0421 (4)
H9A	0.6783	0.4356	0.6820	0.051*
C11	0.73497 (14)	0.1877 (2)	0.49098 (17)	0.0436 (4)
C7	0.42888 (13)	0.27715 (18)	0.72121 (16)	0.0385 (4)
C10	0.75036 (14)	0.3019 (2)	0.57244 (17)	0.0447 (4)
H10A	0.8147	0.3406	0.5908	0.054*
C6	0.30658 (13)	0.48409 (19)	0.71993 (19)	0.0473 (5)
H6A	0.3479	0.5258	0.6603	0.057*
H6B	0.3021	0.5549	0.7851	0.057*
C2	0.29344 (15)	0.2735 (2)	0.85563 (19)	0.0485 (5)
H2B	0.2864	0.3352	0.9264	0.058*
H2C	0.3281	0.1847	0.8840	0.058*
C4	0.13554 (16)	0.3713 (3)	0.7433 (2)	0.0639 (6)
H4A	0.1244	0.4363	0.8119	0.077*
C5	0.20188 (15)	0.4518 (3)	0.6593 (2)	0.0567 (5)
H5A	0.2079	0.3931	0.5866	0.068*
H5B	0.1694	0.5431	0.6335	0.068*
C3	0.19038 (16)	0.2355 (3)	0.7956 (2)	0.0587 (6)
H3A	0.1508	0.1902	0.8554	0.070*
H3B	0.1971	0.1657	0.7302	0.070*
C1	0.0326 (2)	0.3348 (5)	0.6765 (4)	0.1222 (14)
H1A	0.0004	0.4231	0.6459	0.183*
H1B	−0.0088	0.2881	0.7323	0.183*
H1C	0.0415	0.2701	0.6094	0.183*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0609 (4)	0.0796 (5)	0.0696 (4)	0.0091 (3)	0.0222 (3)	−0.0124 (3)
O1	0.0568 (8)	0.0314 (6)	0.0577 (8)	0.0031 (6)	0.0080 (7)	0.0042 (6)
C8	0.0391 (9)	0.0341 (9)	0.0402 (9)	0.0000 (7)	0.0026 (7)	0.0040 (7)
N2	0.0428 (8)	0.0294 (7)	0.0585 (10)	0.0012 (6)	0.0104 (7)	0.0010 (7)
C12	0.0547 (11)	0.0415 (10)	0.0392 (10)	−0.0005 (8)	0.0029 (9)	−0.0049 (8)
C13	0.0443 (10)	0.0431 (10)	0.0418 (10)	−0.0047 (8)	−0.0034 (8)	−0.0020 (8)
N1	0.0400 (8)	0.0375 (8)	0.0575 (10)	0.0021 (6)	0.0089 (7)	0.0060 (7)
C9	0.0454 (10)	0.0371 (9)	0.0439 (10)	−0.0064 (8)	0.0044 (8)	−0.0028 (8)
C11	0.0473 (10)	0.0453 (10)	0.0389 (9)	0.0021 (8)	0.0082 (8)	0.0028 (8)
C7	0.0400 (9)	0.0340 (9)	0.0406 (9)	−0.0016 (7)	0.0002 (8)	−0.0005 (7)
C10	0.0406 (9)	0.0485 (11)	0.0453 (10)	−0.0060 (8)	0.0053 (8)	−0.0011 (8)
C6	0.0474 (10)	0.0351 (9)	0.0600 (12)	0.0049 (8)	0.0080 (9)	0.0012 (8)
C2	0.0516 (11)	0.0455 (10)	0.0496 (11)	−0.0007 (9)	0.0109 (9)	0.0035 (9)
C4	0.0430 (11)	0.0858 (17)	0.0633 (14)	−0.0028 (11)	0.0065 (10)	0.0013 (12)
C5	0.0482 (11)	0.0655 (13)	0.0561 (12)	0.0051 (10)	0.0030 (10)	0.0064 (11)
C3	0.0559 (12)	0.0610 (13)	0.0609 (13)	−0.0165 (10)	0.0141 (10)	0.0005 (10)
C1	0.0510 (15)	0.184 (4)	0.128 (3)	−0.027 (2)	−0.0114 (18)	0.031 (3)

Geometric parameters (Å, º) top

Cl1—C11	1.7441 (19)	C6—C5	1.514 (3)
O1—C7	1.237 (2)	C6—H6A	0.9700
C8—C9	1.384 (2)	C6—H6B	0.9700
C8—C13	1.384 (2)	C2—C3	1.503 (3)
C8—N2	1.416 (2)	C2—H2B	0.9700
N2—C7	1.379 (2)	C2—H2C	0.9700
N2—H2A	0.8600	C4—C5	1.522 (3)
C12—C11	1.381 (3)	C4—C3	1.524 (3)
C12—C13	1.382 (3)	C4—C1	1.526 (3)
C12—H12A	0.9300	C4—H4A	0.9800
C13—H13A	0.9300	C5—H5A	0.9700
N1—C7	1.353 (2)	C5—H5B	0.9700
N1—C2	1.462 (2)	C3—H3A	0.9700
N1—C6	1.463 (2)	C3—H3B	0.9700
C9—C10	1.386 (3)	C1—H1A	0.9600
C9—H9A	0.9300	C1—H1B	0.9600
C11—C10	1.377 (3)	C1—H1C	0.9600
C10—H10A	0.9300

C9—C8—C13	119.49 (16)	H6A—C6—H6B	108.1
C9—C8—N2	119.08 (16)	N1—C2—C3	111.16 (17)
C13—C8—N2	121.42 (16)	N1—C2—H2B	109.4
C7—N2—C8	121.65 (14)	C3—C2—H2B	109.4
C7—N2—H2A	119.2	N1—C2—H2C	109.4
C8—N2—H2A	119.2	C3—C2—H2C	109.4
C11—C12—C13	119.19 (17)	H2B—C2—H2C	108.0
C11—C12—H12A	120.4	C5—C4—C3	109.76 (18)
C13—C12—H12A	120.4	C5—C4—C1	111.1 (2)
C12—C13—C8	120.52 (17)	C3—C4—C1	112.2 (2)
C12—C13—H13A	119.7	C5—C4—H4A	107.9
C8—C13—H13A	119.7	C3—C4—H4A	107.9
C7—N1—C2	119.25 (15)	C1—C4—H4A	107.9
C7—N1—C6	124.54 (16)	C6—C5—C4	112.92 (18)
C2—N1—C6	113.70 (15)	C6—C5—H5A	109.0
C8—C9—C10	120.46 (17)	C4—C5—H5A	109.0
C8—C9—H9A	119.8	C6—C5—H5B	109.0
C10—C9—H9A	119.8	C4—C5—H5B	109.0
C10—C11—C12	121.20 (17)	H5A—C5—H5B	107.8
C10—C11—Cl1	119.10 (15)	C2—C3—C4	111.12 (19)
C12—C11—Cl1	119.69 (14)	C2—C3—H3A	109.4
O1—C7—N1	123.05 (16)	C4—C3—H3A	109.4
O1—C7—N2	121.51 (16)	C2—C3—H3B	109.4
N1—C7—N2	115.41 (15)	C4—C3—H3B	109.4
C11—C10—C9	119.13 (17)	H3A—C3—H3B	108.0
C11—C10—H10A	120.4	C4—C1—H1A	109.5
C9—C10—H10A	120.4	C4—C1—H1B	109.5
N1—C6—C5	110.16 (16)	H1A—C1—H1B	109.5
N1—C6—H6A	109.6	C4—C1—H1C	109.5
C5—C6—H6A	109.6	H1A—C1—H1C	109.5
N1—C6—H6B	109.6	H1B—C1—H1C	109.5
C5—C6—H6B	109.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.33	2.940 (2)	128

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇ClN₂O
M_r	252.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.286 (3), 9.1468 (18), 10.957 (2)
β (°)	95.36 (3)
V (Å³)	1325.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.22 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12608, 3038, 1999
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.154, 1.13
No. of reflections	3038
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.33	2.940 (2)	128

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

References

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

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1796

doi:10.1107/S1600536811024123

Open

access