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

Abstract

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,

• a = 12.1993 (14) Å

• b = 8.2012 (9) Å

• c = 33.453 (4) Å

• V = 3347.0 (7) ų

• 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[F ² > 2σ(F ²)] = 0.073

• wR(F ²) = 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

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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812023525/aa2057Isup3.cml

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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%.

Refinement

H atoms were calculated geometrically and refined as riding with C—H distances 0.93–0.97 Å and U_iso(H) = 1.2 U_eq(C)

Figures

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.

Crystal data

C17H25N3O2	F(000) = 1312
Mr = 303.40	Dx = 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

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

Refinement

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(Fo2) + (0.1025P)2 + 3.0609P] where P = (Fo2 + 2Fc2)/3
3272 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.