4-Methyl-N-p-tolyl­piperidine-1-carbox­amide

Li, Y.-F.

doi:10.1107/S1600536812016248

organic compounds

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Volume 68| Part 5| May 2012| Page o1472

doi:10.1107/S1600536812016248

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4-Methyl-N-p-tolylpiperidine-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 26 March 2012; accepted 14 April 2012; online 21 April 2012)

In the title molecule, C₁₄H₂₀N₂O, the piperidine ring has a chair conformation and its N atom is close to planar (bond-angle sum = 357.5°). The dihedral angle between the amide group and the aromatic ring is 47.43 (19)°. In the crystal, molecules are linked into [100] C(4) chains by N—H⋯O hydrogen bonds.

Related literature

For the medicinal properties of related compounds, see: Yang et al. (1997 ). For a related structure, see: Li (2011 ).

Experimental

Crystal data

C₁₄H₂₀N₂O
M_r = 232.32
Orthorhombic, P b c a
a = 9.6192 (19) Å
b = 11.127 (2) Å
c = 26.574 (5) Å
V = 2844.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
21306 measured reflections
2571 independent reflections
1219 reflections with I > 2σ(I)
R_int = 0.115

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.220
S = 1.03
2571 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.89 (3)	2.08 (3)	2.935 (3)	162 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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/S1600536812016248/hb6706sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016248/hb6706Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016248/hb6706Isup3.cml

checkCIF report

Comment top

Some compounds which are related to the title compound have been shown to have medicinal properties (Yang et al., 1997). The structure of the title compound is shown in Fig. 1. The six-membered ring (C2—C6/N1) has a chair conformation. The bond lengths and angles can be compared to those within a related structure (Li, 2011). In the crystal, the molecules are linked into [100] chains by way of N—H···O hydrogen bonds.

Related literature top

For the medicinal properties of related compounds, see: Yang et al. (1997). For a related structure, see: Li (2011).

Experimental top

A mixture of 4-methylpiperidine (0.08 mol), and p-tolylcarbamic chloride (0.08 mol) was stirred in refluxing ethanol (18 ml) for 4 h to afford the title compound (0.056 mol, yield 70%). 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 the title compound showing 30% probability displacement ellipsoids.

4-Methyl-N-p-tolylpiperidine-1-carboxamide top

Crystal data top

C₁₄H₂₀N₂O	F(000) = 1008
M_r = 232.32	D_x = 1.085 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1979 reflections
a = 9.6192 (19) Å	θ = 3.1–27.5°
b = 11.127 (2) Å	µ = 0.07 mm⁻¹
c = 26.574 (5) Å	T = 293 K
V = 2844.3 (9) Å³	Block, colorless
Z = 8	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.115
Graphite monochromator	θ_max = 25.3°, θ_min = 3.1°
ϕ and ω scans	h = −11→10
21306 measured reflections	k = −13→13
2571 independent reflections	l = −31→31

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1032P)² + 0.1575P] where P = (F_o² + 2F_c²)/3
2571 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₂₀N₂O	V = 2844.3 (9) Å³
M_r = 232.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.6192 (19) Å	µ = 0.07 mm⁻¹
b = 11.127 (2) Å	T = 293 K
c = 26.574 (5) Å	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1219 reflections with I > 2σ(I)
21306 measured reflections	R_int = 0.115
2571 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.220	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
2571 reflections	Δρ_min = −0.20 e Å⁻³
166 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.3590 (3)	0.2180 (2)	0.24983 (9)	0.0723 (7)
O1	0.1457 (2)	0.2820 (2)	0.27689 (8)	0.0937 (8)
N1	0.3387 (3)	0.3504 (2)	0.31682 (9)	0.0835 (8)
C8	0.3092 (3)	0.1515 (3)	0.20795 (11)	0.0692 (8)
C7	0.2741 (3)	0.2829 (3)	0.28129 (11)	0.0713 (8)
C13	0.3740 (3)	0.1655 (3)	0.16191 (12)	0.0774 (9)
H13A	0.4486	0.2180	0.1586	0.093*
C12	0.3270 (4)	0.1007 (3)	0.12054 (12)	0.0900 (10)
H12A	0.3714	0.1109	0.0897	0.108*
C9	0.2002 (3)	0.0699 (3)	0.21213 (12)	0.0828 (10)
H9A	0.1574	0.0577	0.2431	0.099*
C11	0.2162 (4)	0.0217 (3)	0.12365 (14)	0.0927 (11)
C5	0.4786 (4)	0.3297 (5)	0.33540 (14)	0.0885 (11)
C10	0.1556 (4)	0.0073 (3)	0.17043 (16)	0.0964 (11)
H10A	0.0822	−0.0464	0.1739	0.116*
C14	0.1648 (5)	−0.0461 (4)	0.07747 (15)	0.1356 (17)
H14A	0.2195	−0.0238	0.0488	0.203*
H14B	0.0691	−0.0264	0.0714	0.203*
H14C	0.1732	−0.1310	0.0832	0.203*
C4	0.2562 (4)	0.4264 (4)	0.35029 (14)	0.1071 (13)
H4A	0.1637	0.4367	0.3364	0.129*
H4B	0.2990	0.5051	0.3529	0.129*
C2	0.3901 (5)	0.3450 (4)	0.42415 (14)	0.1255 (15)
H2B	0.4366	0.4221	0.4299	0.151*
C6	0.4752 (4)	0.2737 (4)	0.38700 (14)	0.1118 (13)
H6A	0.4370	0.1933	0.3844	0.134*
H6B	0.5696	0.2667	0.3995	0.134*
C3	0.2461 (4)	0.3699 (4)	0.40226 (15)	0.1223 (15)
H3A	0.1945	0.2951	0.4000	0.147*
H3B	0.1957	0.4234	0.4245	0.147*
C1	0.3789 (9)	0.2780 (8)	0.47512 (19)	0.254 (4)
H1A	0.4703	0.2653	0.4886	0.381*
H1B	0.3341	0.2019	0.4701	0.381*
H1C	0.3254	0.3254	0.4983	0.381*
H2A	0.448 (3)	0.241 (3)	0.2491 (11)	0.088 (10)*
H5A	0.532 (3)	0.280 (3)	0.3091 (13)	0.101 (10)*
H5B	0.525 (4)	0.399 (4)	0.3365 (12)	0.115 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0617 (16)	0.0876 (18)	0.0677 (16)	−0.0074 (14)	−0.0034 (13)	−0.0075 (14)
O1	0.0612 (14)	0.136 (2)	0.0839 (16)	0.0009 (13)	−0.0030 (11)	−0.0044 (13)
N1	0.0641 (16)	0.114 (2)	0.0720 (17)	0.0103 (14)	−0.0053 (13)	−0.0237 (16)
C8	0.0735 (19)	0.0647 (19)	0.069 (2)	−0.0026 (16)	−0.0056 (15)	0.0013 (15)
C7	0.0629 (19)	0.085 (2)	0.0656 (19)	−0.0019 (17)	0.0031 (16)	0.0086 (17)
C13	0.093 (2)	0.0668 (19)	0.073 (2)	−0.0078 (17)	−0.0045 (17)	−0.0032 (16)
C12	0.124 (3)	0.075 (2)	0.071 (2)	0.006 (2)	−0.012 (2)	−0.0020 (18)
C9	0.086 (2)	0.075 (2)	0.087 (2)	−0.0111 (18)	−0.0064 (18)	0.0081 (18)
C11	0.113 (3)	0.067 (2)	0.099 (3)	0.004 (2)	−0.034 (2)	−0.0082 (19)
C5	0.071 (2)	0.117 (3)	0.078 (2)	−0.007 (2)	0.0001 (17)	−0.025 (2)
C10	0.100 (3)	0.068 (2)	0.121 (3)	−0.0100 (18)	−0.027 (2)	−0.002 (2)
C14	0.170 (4)	0.111 (3)	0.126 (3)	−0.005 (3)	−0.058 (3)	−0.031 (3)
C4	0.090 (2)	0.139 (3)	0.093 (3)	0.023 (2)	−0.002 (2)	−0.031 (2)
C2	0.142 (4)	0.166 (4)	0.069 (2)	0.028 (3)	0.000 (2)	−0.010 (2)
C6	0.113 (3)	0.130 (3)	0.092 (3)	0.020 (3)	−0.017 (2)	−0.014 (2)
C3	0.108 (3)	0.161 (4)	0.097 (3)	0.006 (3)	0.029 (2)	−0.031 (3)
C1	0.344 (11)	0.333 (10)	0.084 (4)	0.090 (8)	0.026 (5)	0.042 (5)

Geometric parameters (Å, º) top

N2—C7	1.374 (4)	C5—H5B	0.89 (4)
N2—C8	1.420 (4)	C10—H10A	0.9300
N2—H2A	0.89 (3)	C14—H14A	0.9600
O1—C7	1.241 (3)	C14—H14B	0.9600
N1—C7	1.357 (4)	C14—H14C	0.9600
N1—C4	1.462 (4)	C4—C3	1.521 (5)
N1—C5	1.452 (4)	C4—H4A	0.9700
C8—C13	1.382 (4)	C4—H4B	0.9700
C8—C9	1.391 (4)	C2—C6	1.508 (5)
C13—C12	1.390 (4)	C2—C3	1.528 (6)
C13—H13A	0.9300	C2—C1	1.550 (6)
C12—C11	1.384 (5)	C2—H2B	0.9800
C12—H12A	0.9300	C6—H6A	0.9700
C9—C10	1.378 (4)	C6—H6B	0.9700
C9—H9A	0.9300	C3—H3A	0.9700
C11—C10	1.382 (5)	C3—H3B	0.9700
C11—C14	1.524 (5)	C1—H1A	0.9600
C5—C6	1.506 (5)	C1—H1B	0.9600
C5—H5A	1.03 (3)	C1—H1C	0.9600

C7—N2—C8	123.4 (3)	H14A—C14—H14B	109.5
C7—N2—H2A	116 (2)	C11—C14—H14C	109.5
C8—N2—H2A	117 (2)	H14A—C14—H14C	109.5
C7—N1—C4	119.7 (3)	H14B—C14—H14C	109.5
C7—N1—C5	125.0 (3)	N1—C4—C3	110.4 (3)
C4—N1—C5	112.8 (3)	N1—C4—H4A	109.6
C13—C8—C9	119.0 (3)	C3—C4—H4A	109.6
C13—C8—N2	118.9 (3)	N1—C4—H4B	109.6
C9—C8—N2	122.1 (3)	C3—C4—H4B	109.6
O1—C7—N1	121.7 (3)	H4A—C4—H4B	108.1
O1—C7—N2	122.0 (3)	C6—C2—C3	109.8 (3)
N1—C7—N2	116.2 (3)	C6—C2—C1	110.9 (4)
C8—C13—C12	119.7 (3)	C3—C2—C1	110.9 (4)
C8—C13—H13A	120.2	C6—C2—H2B	108.4
C12—C13—H13A	120.2	C3—C2—H2B	108.4
C13—C12—C11	122.2 (3)	C1—C2—H2B	108.4
C13—C12—H12A	118.9	C2—C6—C5	112.9 (3)
C11—C12—H12A	118.9	C2—C6—H6A	109.0
C10—C9—C8	120.0 (3)	C5—C6—H6A	109.0
C10—C9—H9A	120.0	C2—C6—H6B	109.0
C8—C9—H9A	120.0	C5—C6—H6B	109.0
C10—C11—C12	116.9 (3)	H6A—C6—H6B	107.8
C10—C11—C14	122.0 (4)	C4—C3—C2	111.3 (3)
C12—C11—C14	121.1 (4)	C4—C3—H3A	109.4
N1—C5—C6	110.8 (3)	C2—C3—H3A	109.4
N1—C5—H5A	108.7 (18)	C4—C3—H3B	109.4
C6—C5—H5A	113.7 (18)	C2—C3—H3B	109.4
N1—C5—H5B	110 (2)	H3A—C3—H3B	108.0
C6—C5—H5B	110 (2)	C2—C1—H1A	109.5
H5A—C5—H5B	104 (3)	C2—C1—H1B	109.5
C9—C10—C11	122.2 (3)	H1A—C1—H1B	109.5
C9—C10—H10A	118.9	C2—C1—H1C	109.5
C11—C10—H10A	118.9	H1A—C1—H1C	109.5
C11—C14—H14A	109.5	H1B—C1—H1C	109.5
C11—C14—H14B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.89 (3)	2.08 (3)	2.935 (3)	162 (3)

Symmetry code: (i) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂O
M_r	232.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.6192 (19), 11.127 (2), 26.574 (5)
V (Å³)	2844.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21306, 2571, 1219
R_int	0.115
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.220, 1.03
No. of reflections	2571
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

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	0.89 (3)	2.08 (3)	2.935 (3)	162 (3)

Symmetry code: (i) x+1/2, y, −z+1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. (2011). Acta Cryst. E67, o1792. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D., Soulier, J. L., Sicsic, S., Mathe-Allainmat, M., Bremont, B., Croci, T., Cardamone, R., Aureggi, G. & Langlois, M. (1997). J. Med. Chem. 40, 608–621. CSD CrossRef CAS PubMed Web of Science Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1472

doi:10.1107/S1600536812016248

Open

access