N (1)-(4-Methyl-phen-yl)piperidine-1,4-dicarboxamide.

In the title compound, C14H19N3O2, the heterocycle adopts a (1)C4 conformation with the N atom being one of the flap atoms. In the crystal, classical N-H⋯O hydrogen bonds and C-H⋯O contacts connect the mol-ecules into a three-dimensional network.

Related literature

For the pharmacological importance of piperidine and its derivatives, see: Chen et al. (2012 ▶); Boja et al. (2011 ▶); Jakubowska et al. (2012 ▶). For puckering analysis of six-membered rings, see: Cremer & Pople (1975 ▶); Boeyens (1978 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H19N3O2

M = 261.32

Monoclinic,

a = 5.0102 (1) Å

b = 28.6642 (7) Å

c = 10.1131 (2) Å

β = 103.113 (1)°

V = 1414.50 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.42 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.966, T max = 0.991

27256 measured reflections

3556 independent reflections

3014 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.06

3556 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047836/bg2489sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047836/bg2489Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047836/bg2489Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047836/bg2489Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H19N3O2	F(000) = 560
Mr = 261.32	Dx = 1.227 Mg m−3
Monoclinic, P21/c	Melting point = 523–521 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0102 (1) Å	Cell parameters from 9992 reflections
b = 28.6642 (7) Å	θ = 2.2–28.3°
c = 10.1131 (2) Å	µ = 0.08 mm−1
β = 103.113 (1)°	T = 200 K
V = 1414.50 (5) Å3	Platelet, colourless
Z = 4	0.42 × 0.25 × 0.11 mm

Bruker APEXII CCD diffractometer	3556 independent reflections
Radiation source: fine-focus sealed tube	3014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.966, Tmax = 0.991	k = −38→38
27256 measured reflections	l = −13→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.3543P] where P = (Fo2 + 2Fc2)/3
3556 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.1615 (2)	0.25725 (3)	0.13744 (9)	0.0434 (2)
O2	0.31030 (17)	0.05523 (3)	0.44661 (12)	0.0459 (3)
N1	0.1515 (2)	0.27199 (3)	0.35689 (10)	0.0330 (2)
H1	0.155 (3)	0.2596 (5)	0.4318 (17)	0.042 (4)*
N2	0.3917 (3)	0.20893 (4)	0.30192 (10)	0.0394 (3)
N3	0.7377 (2)	0.03696 (4)	0.43233 (13)	0.0386 (3)
H3A	0.710 (3)	0.0081 (6)	0.4578 (17)	0.049 (4)*
H3B	0.898 (3)	0.0466 (6)	0.4190 (16)	0.045 (4)*
C1	−0.2229 (5)	0.46134 (6)	0.3273 (2)	0.0767 (6)
H1A	−0.0793	0.4818	0.3082	0.115*
H1B	−0.2613	0.4698	0.4150	0.115*
H1C	−0.3898	0.4649	0.2556	0.115*
C2	0.2337 (3)	0.24678 (4)	0.25859 (11)	0.0310 (2)
C3	0.5469 (3)	0.20076 (4)	0.44066 (12)	0.0368 (3)
H3C	0.4867	0.2229	0.5031	0.044*
H3D	0.7444	0.2060	0.4461	0.044*
C4	0.5025 (2)	0.15119 (4)	0.48297 (12)	0.0321 (2)
H4A	0.3070	0.1467	0.4839	0.039*
H4B	0.6129	0.1456	0.5760	0.039*
C5	0.5848 (2)	0.11644 (4)	0.38535 (12)	0.0301 (2)
H5	0.7851	0.1202	0.3899	0.036*
C6	0.4276 (3)	0.12705 (4)	0.24063 (13)	0.0409 (3)
H6A	0.4911	0.1060	0.1765	0.049*
H6B	0.2297	0.1213	0.2327	0.049*
C7	0.4714 (4)	0.17763 (4)	0.20382 (14)	0.0472 (4)
H7A	0.6666	0.1827	0.2034	0.057*
H7B	0.3604	0.1845	0.1117	0.057*
C8	0.5337 (2)	0.06691 (4)	0.42456 (12)	0.0305 (2)
C11	0.0476 (2)	0.31796 (4)	0.34039 (11)	0.0302 (2)
C12	−0.1339 (3)	0.33220 (5)	0.41605 (15)	0.0455 (3)
H12	−0.2011	0.3104	0.4713	0.055*
C13	−0.2187 (4)	0.37835 (6)	0.41185 (17)	0.0544 (4)
H13	−0.3429	0.3877	0.4653	0.065*
C14	−0.1276 (3)	0.41117 (5)	0.33202 (15)	0.0482 (3)
C15	0.0491 (3)	0.39607 (5)	0.25471 (15)	0.0452 (3)
H15	0.1115	0.4177	0.1972	0.054*
C16	0.1383 (3)	0.35025 (4)	0.25839 (13)	0.0383 (3)
H16	0.2618	0.3409	0.2046	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.0715 (7)	0.0391 (5)	0.0191 (4)	0.0123 (4)	0.0091 (4)	0.0027 (3)
O2	0.0244 (4)	0.0361 (5)	0.0818 (7)	0.0014 (3)	0.0219 (4)	0.0156 (4)
N1	0.0484 (6)	0.0318 (5)	0.0201 (5)	0.0058 (4)	0.0106 (4)	0.0038 (4)
N2	0.0650 (7)	0.0307 (5)	0.0221 (5)	0.0115 (5)	0.0094 (5)	0.0012 (4)
N3	0.0236 (5)	0.0294 (5)	0.0654 (8)	0.0017 (4)	0.0159 (5)	0.0104 (5)
C1	0.1017 (15)	0.0434 (9)	0.0764 (13)	0.0245 (9)	0.0024 (11)	−0.0068 (8)
C2	0.0435 (6)	0.0291 (5)	0.0209 (5)	−0.0002 (4)	0.0083 (4)	0.0012 (4)
C3	0.0458 (7)	0.0307 (6)	0.0301 (6)	0.0028 (5)	0.0011 (5)	0.0018 (4)
C4	0.0347 (6)	0.0338 (6)	0.0265 (6)	0.0043 (4)	0.0042 (4)	0.0054 (4)
C5	0.0241 (5)	0.0282 (5)	0.0410 (6)	0.0009 (4)	0.0135 (4)	0.0063 (4)
C6	0.0620 (8)	0.0311 (6)	0.0324 (6)	0.0079 (5)	0.0162 (6)	−0.0017 (5)
C7	0.0824 (10)	0.0338 (6)	0.0312 (6)	0.0140 (6)	0.0253 (7)	0.0051 (5)
C8	0.0223 (5)	0.0293 (5)	0.0412 (6)	−0.0004 (4)	0.0096 (4)	0.0059 (4)
C11	0.0347 (5)	0.0326 (5)	0.0219 (5)	0.0022 (4)	0.0033 (4)	−0.0010 (4)
C12	0.0540 (8)	0.0451 (7)	0.0429 (7)	0.0076 (6)	0.0224 (6)	0.0027 (6)
C13	0.0629 (9)	0.0538 (9)	0.0502 (9)	0.0195 (7)	0.0205 (7)	−0.0047 (7)
C14	0.0566 (8)	0.0371 (7)	0.0438 (8)	0.0100 (6)	−0.0032 (6)	−0.0054 (6)
C15	0.0570 (8)	0.0345 (6)	0.0403 (7)	−0.0013 (6)	0.0035 (6)	0.0052 (5)
C16	0.0460 (7)	0.0368 (6)	0.0330 (6)	0.0014 (5)	0.0113 (5)	0.0029 (5)

O1—C2	1.2333 (14)	C4—H4B	0.9900
O2—C8	1.2360 (13)	C5—C8	1.5114 (15)
N1—C2	1.3659 (15)	C5—C6	1.5270 (17)
N1—C11	1.4127 (15)	C5—H5	1.0000
N1—H1	0.834 (17)	C6—C7	1.5249 (18)
N2—C2	1.3560 (15)	C6—H6A	0.9900
N2—C7	1.4588 (16)	C6—H6B	0.9900
N2—C3	1.4605 (15)	C7—H7A	0.9900
N3—C8	1.3235 (14)	C7—H7B	0.9900
N3—H3A	0.886 (18)	C11—C12	1.3763 (17)
N3—H3B	0.890 (17)	C11—C16	1.3863 (17)
C1—C14	1.513 (2)	C12—C13	1.387 (2)
C1—H1A	0.9800	C12—H12	0.9500
C1—H1B	0.9800	C13—C14	1.383 (2)
C1—H1C	0.9800	C13—H13	0.9500
C3—C4	1.5151 (16)	C14—C15	1.377 (2)
C3—H3C	0.9900	C15—C16	1.3852 (18)
C3—H3D	0.9900	C15—H15	0.9500
C4—C5	1.5238 (16)	C16—H16	0.9500
C4—H4A	0.9900
C2—N1—C11	124.85 (10)	C6—C5—H5	108.5
C2—N1—H1	119.3 (11)	C7—C6—C5	110.61 (11)
C11—N1—H1	115.8 (11)	C7—C6—H6A	109.5
C2—N2—C7	120.14 (10)	C5—C6—H6A	109.5
C2—N2—C3	125.68 (10)	C7—C6—H6B	109.5
C7—N2—C3	112.74 (10)	C5—C6—H6B	109.5
C8—N3—H3A	117.0 (11)	H6A—C6—H6B	108.1
C8—N3—H3B	120.2 (10)	N2—C7—C6	110.00 (10)
H3A—N3—H3B	122.7 (15)	N2—C7—H7A	109.7
C14—C1—H1A	109.5	C6—C7—H7A	109.7
C14—C1—H1B	109.5	N2—C7—H7B	109.7
H1A—C1—H1B	109.5	C6—C7—H7B	109.7
C14—C1—H1C	109.5	H7A—C7—H7B	108.2
H1A—C1—H1C	109.5	O2—C8—N3	122.17 (11)
H1B—C1—H1C	109.5	O2—C8—C5	121.06 (10)
O1—C2—N2	122.28 (11)	N3—C8—C5	116.76 (10)
O1—C2—N1	121.69 (11)	C12—C11—C16	118.82 (11)
N2—C2—N1	116.01 (10)	C12—C11—N1	118.89 (11)
N2—C3—C4	109.95 (10)	C16—C11—N1	122.10 (11)
N2—C3—H3C	109.7	C11—C12—C13	120.15 (13)
C4—C3—H3C	109.7	C11—C12—H12	119.9
N2—C3—H3D	109.7	C13—C12—H12	119.9
C4—C3—H3D	109.7	C14—C13—C12	121.80 (14)
H3C—C3—H3D	108.2	C14—C13—H13	119.1
C3—C4—C5	110.57 (10)	C12—C13—H13	119.1
C3—C4—H4A	109.5	C15—C14—C13	117.23 (13)
C5—C4—H4A	109.5	C15—C14—C1	121.33 (16)
C3—C4—H4B	109.5	C13—C14—C1	121.42 (16)
C5—C4—H4B	109.5	C14—C15—C16	121.86 (13)
H4A—C4—H4B	108.1	C14—C15—H15	119.1
C8—C5—C4	110.93 (9)	C16—C15—H15	119.1
C8—C5—C6	110.94 (10)	C15—C16—C11	120.11 (12)
C4—C5—C6	109.52 (9)	C15—C16—H16	119.9
C8—C5—H5	108.5	C11—C16—H16	119.9
C4—C5—H5	108.5
C7—N2—C2—O1	−3.0 (2)	C4—C5—C8—O2	50.08 (16)
C3—N2—C2—O1	162.27 (13)	C6—C5—C8—O2	−71.88 (15)
C7—N2—C2—N1	175.02 (12)	C4—C5—C8—N3	−130.68 (12)
C3—N2—C2—N1	−19.70 (19)	C6—C5—C8—N3	107.35 (13)
C11—N1—C2—O1	−18.65 (19)	C2—N1—C11—C12	151.54 (13)
C11—N1—C2—N2	163.31 (11)	C2—N1—C11—C16	−33.52 (18)
C2—N2—C3—C4	134.00 (13)	C16—C11—C12—C13	−1.4 (2)
C7—N2—C3—C4	−59.78 (15)	N1—C11—C12—C13	173.76 (13)
N2—C3—C4—C5	57.39 (13)	C11—C12—C13—C14	0.5 (2)
C3—C4—C5—C8	−178.42 (9)	C12—C13—C14—C15	0.9 (2)
C3—C4—C5—C6	−55.63 (13)	C12—C13—C14—C1	179.54 (16)
C8—C5—C6—C7	177.79 (10)	C13—C14—C15—C16	−1.5 (2)
C4—C5—C6—C7	55.01 (13)	C1—C14—C15—C16	179.85 (15)
C2—N2—C7—C6	−133.78 (13)	C14—C15—C16—C11	0.7 (2)
C3—N2—C7—C6	59.15 (16)	C12—C11—C16—C15	0.76 (19)
C5—C6—C7—N2	−56.27 (16)	N1—C11—C16—C15	−174.18 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.834 (17)	2.128 (17)	2.9481 (13)	167.9 (15)
N3—H3A···O2ii	0.886 (18)	2.071 (18)	2.9451 (14)	168.9 (15)
N3—H3B···O2iii	0.890 (17)	2.034 (17)	2.8875 (13)	160.3 (15)
C3—H3C···O1i	0.99	2.41	3.2987 (17)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.834 (17)	2.128 (17)	2.9481 (13)	167.9 (15)
N3—H3A⋯O2ii	0.886 (18)	2.071 (18)	2.9451 (14)	168.9 (15)
N3—H3B⋯O2iii	0.890 (17)	2.034 (17)	2.8875 (13)	160.3 (15)
C3—H3C⋯O1i	0.99	2.41	3.2987 (17)	149

Symmetry codes: (i) ; (ii) ; (iii) .