1-[(3-Nitro­phen­yl)(piperidin-1-yl)methyl]piperidine

Wang, Z.-Q.; Ma, Y.

doi:10.1107/S1600536812023525

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1941

doi:10.1107/S1600536812023525

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1-[(3-Nitrophenyl)(piperidin-1-yl)methyl]piperidine

Zhe-Qin Wang ^a ^* and Yi Ma ^b

^aCenter of Computers and Networks, Jilin Radio Television University, Jilin, Jilin Province 132001, People's Republic of China, and ^bDepartment of Chemical Engineering, Shandong Polytechnic University, Jinan 250353, People's Republic of China
^*Correspondence e-mail: wangzheqin@sina.com

(Received 3 April 2012; accepted 23 May 2012; online 31 May 2012)

In the crystal structure of the title compound, C₁₇H₂₅N₃O₂, one-dimensional chains are formed via intermolecular C—H⋯O hydrogen bonds along the a axis.

Related literature

For the activities and uses of piperidine and its derivatives, see: Kumar et al. (2010 ); Huang et al. (2008 ); Cardellicchio et al. (2010 ); Wang et al. (2010 ).

Experimental

Crystal data

C₁₇H₂₅N₃O₂
M_r = 303.40
Orthorhombic, P b c a
a = 12.1993 (14) Å
b = 8.2012 (9) Å
c = 33.453 (4) Å
V = 3347.0 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.984
24143 measured reflections
3272 independent reflections
2633 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.231
S = 1.11
3272 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.93	2.43	3.332 (5)	165
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023525/aa2057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023525/aa2057Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023525/aa2057Isup3.cml

checkCIF report

Comment top

Piperidine and its derivatives extensively applied to some areas of bio-chemistry and material chemistry, which exhibit good bioactivities (Cardellicchio et al. 2010; Huang et al. 2008; Kumar et al. 2010). On the other hand, they display non-linear optic second harmonic generation response and ferroelectric properties (Wang et al., 2010).

A view of the title structure is shown in Fig. 1. In the crystal structure, one-dimensional chains are formed via intermolecular C—H···O hydrogen bonds along the a axis (Table 1, Fig. 2).

Related literature top

For the activities and uses of piperidine and its derivatives, see: Kumar et al. (2010); Huang et al. (2008); Cardellicchio et al. (2010); Wang et al. (2010).

Experimental top

1,1'-((3-nitrophenyl)methylene)dipiperidine (0.100 g) was dissolved in the mixed solvent containing ethanol (10 ml) and water (1 ml). The pale-yellow needle crystals suitable for X-ray diffraction were obtained after one week. Analysis found (%): C, 67.52; H, 8.33; N, 13.81%; calcd (%): C, 67.30; H, 8.31; N, 13.85%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. A drawing of the title compound, with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. C—H···O interactions in the title compound.

1-[(3-Nitrophenyl)(piperidin-1-yl)methyl]piperidine top

Crystal data top

C₁₇H₂₅N₃O₂	F(000) = 1312
M_r = 303.40	D_x = 1.204 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8288 reflections
a = 12.1993 (14) Å	θ = 2.5–27.3°
b = 8.2012 (9) Å	µ = 0.08 mm⁻¹
c = 33.453 (4) Å	T = 296 K
V = 3347.0 (7) Å³	Needle, pale-yellow
Z = 8	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3272 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.981, T_max = 0.984	k = −9→10
24143 measured reflections	l = −41→40

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1025P)² + 3.0609P] where P = (F_o² + 2F_c²)/3
3272 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₂₅N₃O₂	V = 3347.0 (7) Å³
M_r = 303.40	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.1993 (14) Å	µ = 0.08 mm⁻¹
b = 8.2012 (9) Å	T = 296 K
c = 33.453 (4) Å	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3272 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2633 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.032
24143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.11	Δρ_max = 0.60 e Å⁻³
3272 reflections	Δρ_min = −0.32 e Å⁻³
199 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.4378 (2)	0.0644 (3)	0.59215 (7)	0.0407 (6)
C2	0.3469 (2)	0.0225 (3)	0.56963 (8)	0.0464 (7)
H2A	0.2791	0.0697	0.5748	0.056*
C3	0.3587 (2)	−0.0929 (4)	0.53875 (8)	0.0500 (7)
C4	0.4570 (3)	−0.1650 (4)	0.53052 (9)	0.0555 (8)
H4A	0.4625	−0.2418	0.5101	0.067*
C5	0.5477 (3)	−0.1236 (4)	0.55250 (9)	0.0564 (8)
H5A	0.6150	−0.1721	0.5471	0.068*
C6	0.5383 (2)	−0.0096 (4)	0.58258 (8)	0.0493 (7)
H6A	0.6005	0.0193	0.5970	0.059*
C7	0.4282 (2)	0.1804 (3)	0.62769 (7)	0.0375 (6)
H7A	0.3635	0.2493	0.6235	0.045*
C8	0.5060 (2)	−0.0124 (4)	0.67719 (8)	0.0465 (7)
H8A	0.5742	0.0475	0.6749	0.056*
H8B	0.5092	−0.1051	0.6592	0.056*
C9	0.4918 (3)	−0.0723 (4)	0.72010 (9)	0.0549 (8)
H9A	0.5522	−0.1436	0.7271	0.066*
H9B	0.4926	0.0200	0.7382	0.066*
C10	0.3842 (3)	−0.1638 (4)	0.72440 (9)	0.0545 (7)
H10A	0.3730	−0.1934	0.7522	0.065*
H10B	0.3868	−0.2632	0.7087	0.065*
C11	0.2898 (3)	−0.0577 (4)	0.71015 (9)	0.0566 (8)
H11A	0.2225	−0.1205	0.7106	0.068*
H11B	0.2811	0.0341	0.7282	0.068*
C12	0.3100 (2)	0.0049 (4)	0.66804 (8)	0.0472 (7)
H12A	0.3115	−0.0863	0.6496	0.057*
H12B	0.2506	0.0767	0.6602	0.057*
C13	0.5397 (3)	0.3828 (4)	0.59340 (8)	0.0496 (7)
H13A	0.4815	0.4628	0.5911	0.060*
H13B	0.5365	0.3119	0.5702	0.060*
C14	0.6505 (3)	0.4692 (4)	0.59470 (9)	0.0549 (8)
H14A	0.7087	0.3886	0.5955	0.066*
H14B	0.6598	0.5337	0.5706	0.066*
C15	0.6591 (3)	0.5790 (4)	0.63100 (10)	0.0592 (8)
H15A	0.7333	0.6207	0.6332	0.071*
H15B	0.6099	0.6710	0.6280	0.071*
C16	0.6299 (3)	0.4858 (4)	0.66823 (9)	0.0581 (8)
H16A	0.6256	0.5609	0.6906	0.070*
H16B	0.6874	0.4076	0.6740	0.070*
C17	0.5214 (2)	0.3963 (4)	0.66416 (8)	0.0489 (7)
H17A	0.5070	0.3345	0.6883	0.059*
H17B	0.4626	0.4747	0.6607	0.059*
N1	0.2630 (3)	−0.1308 (4)	0.51498 (8)	0.0670 (8)
N2	0.41423 (16)	0.0934 (3)	0.66589 (6)	0.0372 (5)
N3	0.52421 (17)	0.2863 (3)	0.62994 (6)	0.0389 (5)
O1	0.2761 (3)	−0.2159 (4)	0.48535 (9)	0.1021 (11)
O2	0.1737 (2)	−0.0787 (5)	0.52516 (9)	0.1015 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0456 (14)	0.0432 (14)	0.0334 (12)	−0.0001 (11)	−0.0022 (10)	−0.0005 (10)
C2	0.0489 (15)	0.0501 (15)	0.0401 (14)	−0.0021 (12)	−0.0025 (11)	0.0029 (12)
C3	0.0551 (16)	0.0565 (16)	0.0383 (14)	−0.0136 (14)	−0.0095 (12)	0.0089 (12)
C4	0.074 (2)	0.0512 (17)	0.0409 (15)	0.0023 (15)	0.0015 (14)	−0.0026 (13)
C5	0.0588 (18)	0.0623 (19)	0.0482 (16)	0.0130 (15)	0.0021 (13)	−0.0052 (14)
C6	0.0490 (15)	0.0576 (17)	0.0413 (14)	0.0055 (13)	0.0017 (12)	−0.0045 (12)
C7	0.0347 (12)	0.0407 (13)	0.0371 (13)	0.0028 (10)	0.0001 (9)	−0.0013 (10)
C8	0.0399 (14)	0.0556 (16)	0.0439 (15)	0.0035 (12)	−0.0019 (11)	0.0042 (12)
C9	0.0568 (17)	0.0593 (18)	0.0486 (16)	−0.0007 (14)	−0.0101 (13)	0.0069 (14)
C10	0.0681 (19)	0.0498 (16)	0.0455 (15)	−0.0089 (14)	−0.0024 (13)	0.0057 (12)
C11	0.0518 (16)	0.0615 (19)	0.0566 (17)	−0.0091 (14)	0.0087 (13)	0.0058 (15)
C12	0.0374 (14)	0.0520 (16)	0.0522 (16)	−0.0035 (12)	−0.0003 (11)	0.0023 (13)
C13	0.0599 (17)	0.0474 (15)	0.0415 (15)	0.0012 (13)	0.0030 (12)	0.0036 (12)
C14	0.0605 (18)	0.0465 (15)	0.0578 (18)	−0.0044 (14)	0.0179 (14)	0.0055 (13)
C15	0.0619 (18)	0.0430 (15)	0.073 (2)	−0.0094 (14)	0.0103 (15)	−0.0014 (14)
C16	0.0659 (19)	0.0538 (17)	0.0547 (17)	−0.0154 (15)	0.0014 (14)	−0.0110 (14)
C17	0.0556 (16)	0.0473 (15)	0.0436 (15)	−0.0056 (13)	0.0081 (12)	−0.0091 (12)
N1	0.0709 (19)	0.077 (2)	0.0527 (15)	−0.0188 (16)	−0.0139 (14)	0.0004 (14)
N2	0.0347 (11)	0.0395 (11)	0.0373 (11)	−0.0002 (9)	0.0013 (8)	−0.0005 (9)
N3	0.0419 (11)	0.0413 (12)	0.0335 (10)	−0.0029 (9)	0.0036 (8)	−0.0016 (8)
O1	0.105 (2)	0.126 (3)	0.0762 (17)	−0.013 (2)	−0.0286 (16)	−0.0419 (19)
O2	0.0589 (16)	0.154 (3)	0.091 (2)	−0.0134 (18)	−0.0165 (14)	−0.022 (2)

Geometric parameters (Å, º) top

C1—C2	1.384 (4)	C11—C12	1.519 (4)
C1—C6	1.405 (4)	C11—H11A	0.9700
C1—C7	1.527 (3)	C11—H11B	0.9700
C2—C3	1.408 (4)	C12—N2	1.466 (3)
C2—H2A	0.9300	C12—H12A	0.9700
C3—C4	1.366 (4)	C12—H12B	0.9700
C3—N1	1.447 (4)	C13—N3	1.469 (3)
C4—C5	1.371 (5)	C13—C14	1.527 (4)
C4—H4A	0.9300	C13—H13A	0.9700
C5—C6	1.378 (4)	C13—H13B	0.9700
C5—H5A	0.9300	C14—C15	1.515 (4)
C6—H6A	0.9300	C14—H14A	0.9700
C7—N3	1.460 (3)	C14—H14B	0.9700
C7—N2	1.473 (3)	C15—C16	1.504 (4)
C7—H7A	0.9800	C15—H15A	0.9700
C8—N2	1.466 (3)	C15—H15B	0.9700
C8—C9	1.527 (4)	C16—C17	1.520 (4)
C8—H8A	0.9700	C16—H16A	0.9700
C8—H8B	0.9700	C16—H16B	0.9700
C9—C10	1.518 (4)	C17—N3	1.458 (3)
C9—H9A	0.9700	C17—H17A	0.9700
C9—H9B	0.9700	C17—H17B	0.9700
C10—C11	1.521 (4)	N1—O2	1.219 (4)
C10—H10A	0.9700	N1—O1	1.223 (4)
C10—H10B	0.9700

C2—C1—C6	117.9 (2)	H11A—C11—H11B	108.0
C2—C1—C7	121.1 (2)	N2—C12—C11	110.7 (2)
C6—C1—C7	120.9 (2)	N2—C12—H12A	109.5
C1—C2—C3	119.0 (3)	C11—C12—H12A	109.5
C1—C2—H2A	120.5	N2—C12—H12B	109.5
C3—C2—H2A	120.5	C11—C12—H12B	109.5
C4—C3—C2	121.9 (3)	H12A—C12—H12B	108.1
C4—C3—N1	120.3 (3)	N3—C13—C14	109.9 (2)
C2—C3—N1	117.7 (3)	N3—C13—H13A	109.7
C3—C4—C5	119.5 (3)	C14—C13—H13A	109.7
C3—C4—H4A	120.2	N3—C13—H13B	109.7
C5—C4—H4A	120.2	C14—C13—H13B	109.7
C4—C5—C6	119.5 (3)	H13A—C13—H13B	108.2
C4—C5—H5A	120.2	C15—C14—C13	111.1 (2)
C6—C5—H5A	120.2	C15—C14—H14A	109.4
C5—C6—C1	122.1 (3)	C13—C14—H14A	109.4
C5—C6—H6A	118.9	C15—C14—H14B	109.4
C1—C6—H6A	118.9	C13—C14—H14B	109.4
N3—C7—N2	109.63 (19)	H14A—C14—H14B	108.0
N3—C7—C1	110.41 (19)	C16—C15—C14	110.2 (2)
N2—C7—C1	112.5 (2)	C16—C15—H15A	109.6
N3—C7—H7A	108.1	C14—C15—H15A	109.6
N2—C7—H7A	108.1	C16—C15—H15B	109.6
C1—C7—H7A	108.1	C14—C15—H15B	109.6
N2—C8—C9	110.3 (2)	H15A—C15—H15B	108.1
N2—C8—H8A	109.6	C15—C16—C17	112.2 (3)
C9—C8—H8A	109.6	C15—C16—H16A	109.2
N2—C8—H8B	109.6	C17—C16—H16A	109.2
C9—C8—H8B	109.6	C15—C16—H16B	109.2
H8A—C8—H8B	108.1	C17—C16—H16B	109.2
C10—C9—C8	110.3 (2)	H16A—C16—H16B	107.9
C10—C9—H9A	109.6	N3—C17—C16	110.4 (2)
C8—C9—H9A	109.6	N3—C17—H17A	109.6
C10—C9—H9B	109.6	C16—C17—H17A	109.6
C8—C9—H9B	109.6	N3—C17—H17B	109.6
H9A—C9—H9B	108.1	C16—C17—H17B	109.6
C9—C10—C11	110.0 (2)	H17A—C17—H17B	108.1
C9—C10—H10A	109.7	O2—N1—O1	123.0 (3)
C11—C10—H10A	109.7	O2—N1—C3	119.5 (3)
C9—C10—H10B	109.7	O1—N1—C3	117.5 (3)
C11—C10—H10B	109.7	C8—N2—C12	110.9 (2)
H10A—C10—H10B	108.2	C8—N2—C7	114.97 (19)
C12—C11—C10	111.2 (2)	C12—N2—C7	112.48 (19)
C12—C11—H11A	109.4	C17—N3—C7	112.92 (19)
C10—C11—H11A	109.4	C17—N3—C13	108.8 (2)
C12—C11—H11B	109.4	C7—N3—C13	112.4 (2)
C10—C11—H11B	109.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.43	3.332 (5)	165

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅N₃O₂
M_r	303.40
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.1993 (14), 8.2012 (9), 33.453 (4)
V (Å³)	3347.0 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	24143, 3272, 2633
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.231, 1.11
No. of reflections	3272
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.43	3.332 (5)	165

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

Acknowledgements

The authors acknowledge financial support from the Project of Shandong Province Higher Educational Science and Technology Program (grant No. J09LB03) and Shandong Distinguished Middle-aged and Young Scientist Encouragement and Reward Foundation (grant No. BS2011CL034).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cardellicchio, C., Capozzi, M. A. M. & Naso, F. (2010). Tetrahedron Asymmetry, 21, 507–517. Web of Science CrossRef CAS Google Scholar
Huang, P. J. J., Youssef, D., Cameron, T. S. & Jha, A. (2008). Arkivoc, pp. 165–177. CrossRef Google Scholar
Kumar, A., Gupta, M. K. & Kumar, M. (2010). Tetrahedron Lett. 51, 1582–1584. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y. T., Tang, G. M., Li, T. D., Yu, J. C., Wei, Y. Q., Ling, J. B. & Long, X. F. (2010). Aust. J. Chem. 63, 336–342. Web of Science CSD CrossRef CAS Google Scholar