4-[4-(Piperidin-1-yl)piperidin-1-yl]benzonitrile.

In the title compound, C(17)H(23)N(3), both piperidine rings adopt chair conformations. In the crystal packing, intermolecular C-H⋯N hydrogen bonds and C-H⋯π interactions are present.

Related literature

For general background, see: Pevarello et al. (2006 ▶).

Experimental

Crystal data

C17H23N3

M = 269.38

Monoclinic,

a = 10.090 (2) Å

b = 11.100 (2) Å

c = 13.446 (3) Å

β = 100.72 (3)°

V = 1479.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 113 K

0.26 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.981, T max = 0.986

11970 measured reflections

3500 independent reflections

2749 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.12

3500 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ChemBioDraw Ultra CambridgeSoft (2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905507X/kp2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905507X/kp2240Isup2.hkl

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

C17H23N3	F(000) = 584
Mr = 269.38	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4488 reflections
a = 10.090 (2) Å	θ = 2.7–27.9°
b = 11.100 (2) Å	µ = 0.07 mm−1
c = 13.446 (3) Å	T = 113 K
β = 100.72 (3)°	Block, red
V = 1479.7 (5) Å3	0.26 × 0.25 × 0.20 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3500 independent reflections
Radiation source: rotating anode	2749 reflections with I > 2σ(I)
confocal	Rint = 0.032
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.8°
ω and φ scans	h = −13→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −14→14
Tmin = 0.981, Tmax = 0.986	l = −17→17
11970 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.0668P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
3500 reflections	Δρmax = 0.27 e Å−3
182 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (7)

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.

	x	y	z	Uiso*/Ueq
N1	0.19321 (8)	0.59022 (8)	0.73578 (6)	0.0193 (2)
N2	0.26675 (8)	0.49828 (7)	0.43659 (6)	0.0187 (2)
N3	0.48688 (9)	0.35177 (8)	0.00345 (7)	0.0256 (2)
C1	0.21163 (10)	0.49931 (10)	0.81631 (8)	0.0225 (2)
H1A	0.3069	0.4727	0.8304	0.027*
H1B	0.1547	0.4283	0.7934	0.027*
C2	0.17411 (11)	0.54896 (10)	0.91273 (8)	0.0270 (3)
H2A	0.2363	0.6154	0.9391	0.032*
H2B	0.1839	0.4848	0.9647	0.032*
C3	0.02945 (11)	0.59541 (11)	0.89283 (9)	0.0310 (3)
H3A	−0.0339	0.5270	0.8768	0.037*
H3B	0.0102	0.6360	0.9542	0.037*
C4	0.00956 (11)	0.68349 (11)	0.80492 (9)	0.0307 (3)
H4A	0.0638	0.7569	0.8249	0.037*
H4B	−0.0865	0.7074	0.7881	0.037*
C5	0.05156 (10)	0.62790 (11)	0.71205 (8)	0.0274 (3)
H5A	−0.0062	0.5573	0.6894	0.033*
H5B	0.0392	0.6875	0.6563	0.033*
C6	0.24849 (10)	0.54949 (9)	0.64737 (8)	0.0182 (2)
H6	0.3448	0.5272	0.6733	0.022*
C7	0.18209 (10)	0.43925 (9)	0.59102 (8)	0.0205 (2)
H7A	0.1816	0.3721	0.6394	0.025*
H7B	0.0873	0.4584	0.5608	0.025*
C8	0.25693 (10)	0.40038 (9)	0.50799 (8)	0.0204 (2)
H8A	0.3488	0.3734	0.5391	0.024*
H8B	0.2093	0.3313	0.4708	0.024*
C9	0.32454 (11)	0.60897 (9)	0.48736 (8)	0.0224 (2)
H9A	0.3206	0.6742	0.4366	0.027*
H9B	0.4206	0.5948	0.5172	0.027*
C10	0.25036 (11)	0.64891 (9)	0.56997 (8)	0.0229 (2)
H10A	0.1566	0.6711	0.5394	0.027*
H10B	0.2951	0.7211	0.6042	0.027*
C11	0.31345 (9)	0.46754 (9)	0.34801 (7)	0.0179 (2)
C12	0.32252 (10)	0.55520 (9)	0.27405 (8)	0.0209 (2)
H12	0.2976	0.6360	0.2849	0.025*
C13	0.36689 (10)	0.52613 (9)	0.18606 (8)	0.0212 (2)
H13	0.3727	0.5870	0.1374	0.025*
C14	0.40341 (10)	0.40774 (9)	0.16801 (8)	0.0182 (2)
C15	0.39452 (10)	0.31974 (9)	0.24037 (8)	0.0203 (2)
H15	0.4191	0.2390	0.2289	0.024*
C16	0.35023 (10)	0.34886 (9)	0.32857 (8)	0.0205 (2)
H16	0.3445	0.2876	0.3770	0.025*
C17	0.45003 (10)	0.37726 (9)	0.07679 (8)	0.0200 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0189 (4)	0.0234 (5)	0.0162 (4)	0.0020 (3)	0.0049 (3)	−0.0006 (3)
N2	0.0253 (4)	0.0146 (4)	0.0169 (4)	−0.0026 (3)	0.0060 (3)	−0.0002 (3)
N3	0.0337 (5)	0.0195 (5)	0.0252 (5)	−0.0013 (4)	0.0101 (4)	−0.0025 (4)
C1	0.0240 (5)	0.0248 (5)	0.0194 (5)	0.0000 (4)	0.0053 (4)	0.0015 (4)
C2	0.0287 (6)	0.0343 (6)	0.0190 (6)	−0.0034 (5)	0.0071 (4)	−0.0014 (5)
C3	0.0272 (6)	0.0414 (7)	0.0273 (6)	−0.0046 (5)	0.0127 (5)	−0.0073 (5)
C4	0.0237 (5)	0.0400 (7)	0.0300 (6)	0.0065 (5)	0.0085 (5)	−0.0051 (5)
C5	0.0215 (5)	0.0370 (6)	0.0237 (6)	0.0071 (5)	0.0044 (4)	−0.0020 (5)
C6	0.0183 (5)	0.0197 (5)	0.0170 (5)	0.0005 (4)	0.0045 (4)	−0.0008 (4)
C7	0.0226 (5)	0.0200 (5)	0.0196 (5)	−0.0024 (4)	0.0058 (4)	0.0011 (4)
C8	0.0272 (5)	0.0160 (5)	0.0189 (5)	−0.0022 (4)	0.0069 (4)	0.0008 (4)
C9	0.0287 (5)	0.0187 (5)	0.0210 (5)	−0.0062 (4)	0.0076 (4)	−0.0031 (4)
C10	0.0315 (6)	0.0177 (5)	0.0212 (6)	−0.0024 (4)	0.0094 (4)	−0.0023 (4)
C11	0.0178 (5)	0.0183 (5)	0.0170 (5)	−0.0011 (4)	0.0018 (4)	−0.0009 (4)
C12	0.0263 (5)	0.0161 (5)	0.0209 (5)	0.0028 (4)	0.0059 (4)	0.0000 (4)
C13	0.0268 (5)	0.0187 (5)	0.0185 (5)	0.0012 (4)	0.0054 (4)	0.0027 (4)
C14	0.0196 (5)	0.0181 (5)	0.0171 (5)	−0.0009 (4)	0.0033 (4)	−0.0014 (4)
C15	0.0238 (5)	0.0164 (5)	0.0205 (6)	0.0007 (4)	0.0033 (4)	−0.0017 (4)
C16	0.0253 (5)	0.0170 (5)	0.0187 (5)	−0.0007 (4)	0.0031 (4)	0.0011 (4)
C17	0.0236 (5)	0.0145 (5)	0.0216 (6)	−0.0012 (4)	0.0038 (4)	0.0000 (4)

N1—C5	1.4663 (13)	C6—H6	1.0000
N1—C1	1.4664 (13)	C7—C8	1.5219 (14)
N1—C6	1.4749 (13)	C7—H7A	0.9900
N2—C11	1.4020 (13)	C7—H7B	0.9900
N2—C8	1.4656 (13)	C8—H8A	0.9900
N2—C9	1.4723 (13)	C8—H8B	0.9900
N3—C17	1.1520 (13)	C9—C10	1.5164 (14)
C1—C2	1.5200 (14)	C9—H9A	0.9900
C1—H1A	0.9900	C9—H9B	0.9900
C1—H1B	0.9900	C10—H10A	0.9900
C2—C3	1.5241 (16)	C10—H10B	0.9900
C2—H2A	0.9900	C11—C16	1.4063 (14)
C2—H2B	0.9900	C11—C12	1.4064 (14)
C3—C4	1.5183 (17)	C12—C13	1.3788 (14)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.3981 (14)
C4—C5	1.5220 (15)	C13—H13	0.9500
C4—H4A	0.9900	C14—C15	1.3933 (14)
C4—H4B	0.9900	C14—C17	1.4335 (14)
C5—H5A	0.9900	C15—C16	1.3811 (14)
C5—H5B	0.9900	C15—H15	0.9500
C6—C10	1.5195 (14)	C16—H16	0.9500
C6—C7	1.5269 (14)
C5—N1—C1	109.98 (8)	C8—C7—H7A	109.4
C5—N1—C6	114.29 (8)	C6—C7—H7A	109.4
C1—N1—C6	111.67 (8)	C8—C7—H7B	109.4
C11—N2—C8	116.77 (8)	C6—C7—H7B	109.4
C11—N2—C9	115.49 (8)	H7A—C7—H7B	108.0
C8—N2—C9	112.59 (8)	N2—C8—C7	111.93 (8)
N1—C1—C2	111.27 (9)	N2—C8—H8A	109.2
N1—C1—H1A	109.4	C7—C8—H8A	109.2
C2—C1—H1A	109.4	N2—C8—H8B	109.2
N1—C1—H1B	109.4	C7—C8—H8B	109.2
C2—C1—H1B	109.4	H8A—C8—H8B	107.9
H1A—C1—H1B	108.0	N2—C9—C10	112.14 (8)
C1—C2—C3	110.81 (9)	N2—C9—H9A	109.2
C1—C2—H2A	109.5	C10—C9—H9A	109.2
C3—C2—H2A	109.5	N2—C9—H9B	109.2
C1—C2—H2B	109.5	C10—C9—H9B	109.2
C3—C2—H2B	109.5	H9A—C9—H9B	107.9
H2A—C2—H2B	108.1	C9—C10—C6	111.10 (8)
C4—C3—C2	109.76 (9)	C9—C10—H10A	109.4
C4—C3—H3A	109.7	C6—C10—H10A	109.4
C2—C3—H3A	109.7	C9—C10—H10B	109.4
C4—C3—H3B	109.7	C6—C10—H10B	109.4
C2—C3—H3B	109.7	H10A—C10—H10B	108.0
H3A—C3—H3B	108.2	N2—C11—C16	121.86 (9)
C3—C4—C5	111.16 (10)	N2—C11—C12	120.57 (9)
C3—C4—H4A	109.4	C16—C11—C12	117.55 (9)
C5—C4—H4A	109.4	C13—C12—C11	121.27 (9)
C3—C4—H4B	109.4	C13—C12—H12	119.4
C5—C4—H4B	109.4	C11—C12—H12	119.4
H4A—C4—H4B	108.0	C12—C13—C14	120.46 (9)
N1—C5—C4	110.24 (9)	C12—C13—H13	119.8
N1—C5—H5A	109.6	C14—C13—H13	119.8
C4—C5—H5A	109.6	C15—C14—C13	118.98 (9)
N1—C5—H5B	109.6	C15—C14—C17	120.39 (9)
C4—C5—H5B	109.6	C13—C14—C17	120.63 (9)
H5A—C5—H5B	108.1	C16—C15—C14	120.57 (9)
N1—C6—C10	112.59 (8)	C16—C15—H15	119.7
N1—C6—C7	116.67 (8)	C14—C15—H15	119.7
C10—C6—C7	107.60 (8)	C15—C16—C11	121.17 (9)
N1—C6—H6	106.4	C15—C16—H16	119.4
C10—C6—H6	106.4	C11—C16—H16	119.4
C7—C6—H6	106.4	N3—C17—C14	179.37 (11)
C8—C7—C6	111.06 (8)
C5—N1—C1—C2	−60.67 (11)	N2—C9—C10—C6	56.38 (12)
C6—N1—C1—C2	171.35 (8)	N1—C6—C10—C9	172.41 (8)
N1—C1—C2—C3	56.80 (12)	C7—C6—C10—C9	−57.65 (11)
C1—C2—C3—C4	−52.73 (12)	C8—N2—C11—C16	−0.48 (13)
C2—C3—C4—C5	53.76 (12)	C9—N2—C11—C16	135.34 (10)
C1—N1—C5—C4	60.92 (12)	C8—N2—C11—C12	178.25 (9)
C6—N1—C5—C4	−172.56 (9)	C9—N2—C11—C12	−45.93 (12)
C3—C4—C5—N1	−58.25 (12)	N2—C11—C12—C13	−179.30 (9)
C5—N1—C6—C10	63.26 (11)	C16—C11—C12—C13	−0.52 (14)
C1—N1—C6—C10	−171.10 (8)	C11—C12—C13—C14	0.37 (15)
C5—N1—C6—C7	−61.87 (12)	C12—C13—C14—C15	−0.13 (15)
C1—N1—C6—C7	63.77 (11)	C12—C13—C14—C17	−179.78 (9)
N1—C6—C7—C8	−174.76 (8)	C13—C14—C15—C16	0.05 (15)
C10—C6—C7—C8	57.63 (11)	C17—C14—C15—C16	179.70 (9)
C11—N2—C8—C7	−169.71 (8)	C14—C15—C16—C11	−0.21 (15)
C9—N2—C8—C7	53.24 (11)	N2—C11—C16—C15	179.21 (9)
C6—C7—C8—N2	−56.30 (11)	C12—C11—C16—C15	0.44 (15)
C11—N2—C9—C10	169.02 (8)	C15—C14—C17—N3	38 (9)
C8—N2—C9—C10	−53.35 (11)	C13—C14—C17—N3	−142 (9)

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgi	1.00	2.99	3.9363 (14)	158
C16—H16···N3ii	0.95	2.54	3.3442 (16)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgi	1.00	2.99	3.9363 (14)	158
C16—H16⋯N3ii	0.95	2.54	3.3442 (16)	143

Symmetry codes: (i) ; (ii) .