N,N-Bis(pyridin-2-ylmeth-yl)cyclo-hexa-namine.

The pyridine rings of the title compound, C(18)H(23)N(3), are in a nearly perpendicular orientation relative to the plane defined by the three amino-bonded C atoms, making dihedral angles of 87.4 (1) ° and 84.2 (1) °. One of the pyridine N atoms acts as an hydrogen-bond acceptor for two pyridine C-H groups. By means of these intermolecular hydrogen bonds, the mol-ecules form a two-dimensional network parallel to the ab plane.

Related literature

For a kinetic and mechanistic study of the platinum(II) chelate of the title compound, see: Mambanda & Jaganyi (2012 ▶). For the synthesis of the title compound, see: Sato et al. (1992 ▶); Toftlund & Yde-Andersen (1981 ▶); Anderegg & Wenk (1967 ▶). For the crystal structure of the related compound N,N-bis­(2-pyridyl­meth­yl)-tert-butyl­amine, see: Mambanda et al. (2009 ▶). For the crystal structures of the hexa­dentate analogues, see: Mambanda et al. (2007 ▶). For dinuclear platinum(II) complexes structurally related to the complex of the title compound, see: Hofmann & van Eldik (2003 ▶); Erteurk et al. (2007 ▶, 2008 ▶). For dinuclear metal complexes containing bis­(tridentate) chelates structurally related to the title compound, see: Fujihara et al. (2004 ▶); Gunatilleke & Norman (2003 ▶); Fujii et al. (2003 ▶). For manganese–oxo complexes of N,N-bis­(2-pyridyl­meth­yl)ethyl­amine and N,N-bis­ (2-pyridyl­meth­yl)-tert-butyl­amine, see: Pal et al. (1992 ▶) and Mok et al. (1997 ▶), respectively.

Experimental

Crystal data

C18H23N3

M = 281.39

Monoclinic,

a = 6.2272 (2) Å

b = 18.1729 (7) Å

c = 14.3213 (5) Å

β = 102.118 (4)°

V = 1584.57 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.60 × 0.50 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.959, T max = 0.979

7854 measured reflections

2521 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.085

S = 0.98

2134 reflections

190 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027572/ld2063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027572/ld2063Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027572/ld2063Isup3.cml

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

C18H23N3	F(000) = 608
Mr = 281.39	Dx = 1.180 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2134 reflections
a = 6.2272 (2) Å	θ = 3.5–32.1°
b = 18.1729 (7) Å	µ = 0.07 mm−1
c = 14.3213 (5) Å	T = 120 K
β = 102.118 (4)°	Planar, colourless
V = 1584.57 (10) Å3	0.60 × 0.50 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur 2 CCD diffractometer	2521 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans at fixed θ angles	θmax = 32.1°, θmin = 3.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→6
Tmin = 0.959, Tmax = 0.979	k = −26→25
7854 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3
2134 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.15 e Å−3
2 restraints	Δρmin = −0.25 e Å−3

Experimental. Yield: 1.3432 g (40%), colourless block crystals. 1H NMR (400 MHz, CDCl3) δ (p.p.m.): 8.58 (d, 2H); 8.50–7.60 (m, 4H); 7.05 (t, 2H); 3.39 (s, 4H); 2.55 (m, 1H); 1.90 (d, 2H); 1.8 (m, 2H); 1.60 (d, 2H); 1.35 (m, 2H); 1.19 (m, 2H). 13C NMR (100 MHz, CDCl3) δ / p.p.m.: 27.0; 29; 57.0; 60.5; 122.0; 123.0; 136.0; 148.0; 161. IR (KBr, 4000–400 cm-1): 2958–2854 (alkyl C—H stretch); 1589 C=N (pyridyl). MS—ES+, m/e: 282.2069, (M +1)+. Anal. Calc. for C18H23N3: C, 76.81; H, 8.24; N, 14.93; Found: C, 76.8; H, 8.18; N, 14.89.

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 > 2σ(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
C1	0.8715 (2)	0.26180 (9)	0.20552 (11)	0.0220 (3)
H1A	1.0103	0.2846	0.1967	0.026*
H1B	0.9082	0.2135	0.2369	0.026*
C2	0.7709 (2)	0.31007 (8)	0.27025 (10)	0.0186 (3)
C3	0.5510 (2)	0.30374 (9)	0.27499 (11)	0.0235 (3)
H3	0.4570	0.2709	0.2338	0.028*
C4	0.4709 (3)	0.34586 (10)	0.34038 (12)	0.0258 (3)
H4	0.3215	0.3420	0.3451	0.031*
C5	0.6111 (3)	0.39369 (10)	0.39884 (12)	0.0265 (3)
H5	0.5610	0.4230	0.4449	0.032*
C6	0.8260 (3)	0.39748 (9)	0.38825 (12)	0.0253 (3)
H6	0.9221	0.4308	0.4278	0.030*
C7	0.7975 (3)	0.18410 (9)	0.06711 (11)	0.0219 (3)
H7A	0.9583	0.1856	0.0719	0.026*
H7B	0.7258	0.1839	−0.0015	0.026*
C8	0.7384 (3)	0.11434 (8)	0.11310 (11)	0.0215 (3)
C9	0.5374 (3)	0.10687 (10)	0.14035 (12)	0.0270 (3)
H9	0.4348	0.1463	0.1310	0.032*
C10	0.4884 (3)	0.04184 (10)	0.18101 (13)	0.0310 (4)
H10	0.3523	0.0358	0.2002	0.037*
C11	0.6412 (3)	−0.01444 (10)	0.19330 (13)	0.0313 (4)
H11	0.6137	−0.0598	0.2216	0.038*
C12	0.8340 (3)	−0.00279 (10)	0.16339 (14)	0.0321 (4)
H12	0.9380	−0.0417	0.1713	0.039*
C13	0.7079 (2)	0.31684 (8)	0.05181 (11)	0.0196 (3)
H13	0.6855	0.3590	0.0936	0.024*
C14	0.9088 (3)	0.33578 (9)	0.01086 (12)	0.0240 (3)
H14A	1.0392	0.3406	0.0636	0.029*
H14B	0.9370	0.2955	−0.0315	0.029*
C15	0.8733 (3)	0.40755 (10)	−0.04551 (13)	0.0304 (4)
H15A	1.0034	0.4179	−0.0730	0.036*
H15B	0.8567	0.4485	−0.0020	0.036*
C16	0.6690 (3)	0.40310 (10)	−0.12573 (12)	0.0295 (4)
H16A	0.6455	0.4510	−0.1593	0.035*
H16B	0.6910	0.3652	−0.1725	0.035*
C17	0.4681 (3)	0.38384 (10)	−0.08605 (12)	0.0285 (4)
H17A	0.3395	0.3782	−0.1395	0.034*
H17B	0.4367	0.4245	−0.0449	0.034*
C18	0.5024 (3)	0.31257 (10)	−0.02789 (12)	0.0250 (3)
H18A	0.3726	0.3034	0.0003	0.030*
H18B	0.5165	0.2709	−0.0707	0.030*
N1	0.7294 (2)	0.24994 (7)	0.11224 (9)	0.0197 (3)
N2	0.9074 (2)	0.35684 (7)	0.32526 (10)	0.0219 (3)
N3	0.8852 (2)	0.05990 (8)	0.12380 (11)	0.0268 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (7)	0.0269 (8)	0.0196 (7)	0.0041 (6)	0.0039 (5)	0.0007 (6)
C2	0.0202 (7)	0.0190 (7)	0.0164 (6)	0.0021 (5)	0.0033 (5)	0.0032 (5)
C3	0.0205 (7)	0.0296 (8)	0.0199 (7)	−0.0015 (6)	0.0031 (6)	−0.0010 (6)
C4	0.0231 (7)	0.0326 (9)	0.0235 (7)	0.0012 (6)	0.0089 (6)	0.0022 (7)
C5	0.0319 (8)	0.0269 (8)	0.0231 (7)	0.0061 (7)	0.0114 (6)	−0.0004 (6)
C6	0.0289 (8)	0.0217 (8)	0.0249 (7)	0.0004 (6)	0.0043 (6)	−0.0015 (6)
C7	0.0248 (7)	0.0214 (7)	0.0212 (7)	0.0019 (6)	0.0090 (6)	0.0002 (6)
C8	0.0253 (7)	0.0221 (7)	0.0173 (6)	−0.0018 (6)	0.0049 (6)	−0.0011 (6)
C9	0.0246 (8)	0.0273 (8)	0.0302 (8)	−0.0003 (6)	0.0081 (7)	−0.0021 (7)
C10	0.0311 (8)	0.0324 (9)	0.0317 (9)	−0.0092 (7)	0.0114 (7)	−0.0034 (7)
C11	0.0393 (10)	0.0259 (8)	0.0277 (8)	−0.0097 (7)	0.0048 (7)	0.0014 (7)
C12	0.0336 (9)	0.0242 (9)	0.0384 (10)	0.0013 (7)	0.0072 (8)	0.0044 (8)
C13	0.0198 (7)	0.0208 (7)	0.0187 (6)	0.0015 (6)	0.0049 (5)	−0.0010 (6)
C14	0.0224 (7)	0.0251 (8)	0.0248 (7)	−0.0013 (6)	0.0058 (6)	0.0008 (6)
C15	0.0363 (9)	0.0266 (9)	0.0282 (8)	−0.0056 (7)	0.0065 (7)	0.0020 (7)
C16	0.0395 (10)	0.0269 (8)	0.0211 (7)	0.0012 (7)	0.0041 (7)	0.0029 (6)
C17	0.0291 (8)	0.0307 (8)	0.0234 (7)	0.0062 (7)	0.0002 (6)	0.0014 (7)
C18	0.0205 (7)	0.0295 (8)	0.0238 (7)	0.0003 (6)	0.0016 (6)	0.0027 (6)
N1	0.0226 (6)	0.0211 (6)	0.0157 (6)	0.0025 (5)	0.0048 (5)	−0.0003 (5)
N2	0.0215 (6)	0.0202 (6)	0.0238 (6)	0.0006 (5)	0.0040 (5)	0.0008 (5)
N3	0.0282 (7)	0.0224 (7)	0.0308 (7)	0.0022 (6)	0.0080 (6)	0.0018 (6)

C1—N1	1.4554 (19)	C10—H10	0.9500
C1—C2	1.505 (2)	C11—C12	1.373 (3)
C1—H1A	0.9900	C11—H11	0.9500
C1—H1B	0.9900	C12—N3	1.341 (2)
C2—N2	1.3359 (19)	C12—H12	0.9500
C2—C3	1.390 (2)	C13—N1	1.4821 (19)
C3—C4	1.381 (2)	C13—C18	1.528 (2)
C3—H3	0.9500	C13—C14	1.528 (2)
C4—C5	1.383 (2)	C13—H13	1.0000
C4—H4	0.9500	C14—C15	1.526 (2)
C5—C6	1.380 (2)	C14—H14A	0.9900
C5—H5	0.9500	C14—H14B	0.9900
C6—N2	1.345 (2)	C15—C16	1.527 (2)
C6—H6	0.9500	C15—H15A	0.9900
C7—N1	1.4642 (19)	C15—H15B	0.9900
C7—C8	1.509 (2)	C16—C17	1.520 (3)
C7—H7A	0.9900	C16—H16A	0.9900
C7—H7B	0.9900	C16—H16B	0.9900
C8—N3	1.334 (2)	C17—C18	1.530 (2)
C8—C9	1.394 (2)	C17—H17A	0.9900
C9—C10	1.380 (2)	C17—H17B	0.9900
C9—H9	0.9500	C18—H18A	0.9900
C10—C11	1.383 (3)	C18—H18B	0.9900
N1—C1—C2	113.59 (12)	N1—C13—C18	110.69 (13)
N1—C1—H1A	108.8	N1—C13—C14	115.35 (12)
C2—C1—H1A	108.8	C18—C13—C14	110.47 (13)
N1—C1—H1B	108.8	N1—C13—H13	106.6
C2—C1—H1B	108.8	C18—C13—H13	106.6
H1A—C1—H1B	107.7	C14—C13—H13	106.6
N2—C2—C3	122.37 (14)	C15—C14—C13	110.87 (14)
N2—C2—C1	116.00 (13)	C15—C14—H14A	109.5
C3—C2—C1	121.58 (14)	C13—C14—H14A	109.5
C4—C3—C2	119.13 (15)	C15—C14—H14B	109.5
C4—C3—H3	120.4	C13—C14—H14B	109.5
C2—C3—H3	120.4	H14A—C14—H14B	108.1
C3—C4—C5	119.17 (15)	C14—C15—C16	110.99 (14)
C3—C4—H4	120.4	C14—C15—H15A	109.4
C5—C4—H4	120.4	C16—C15—H15A	109.4
C6—C5—C4	117.92 (15)	C14—C15—H15B	109.4
C6—C5—H5	121.0	C16—C15—H15B	109.4
C4—C5—H5	121.0	H15A—C15—H15B	108.0
N2—C6—C5	123.87 (16)	C17—C16—C15	110.62 (14)
N2—C6—H6	118.1	C17—C16—H16A	109.5
C5—C6—H6	118.1	C15—C16—H16A	109.5
N1—C7—C8	111.97 (12)	C17—C16—H16B	109.5
N1—C7—H7A	109.2	C15—C16—H16B	109.5
C8—C7—H7A	109.2	H16A—C16—H16B	108.1
N1—C7—H7B	109.2	C16—C17—C18	111.50 (14)
C8—C7—H7B	109.2	C16—C17—H17A	109.3
H7A—C7—H7B	107.9	C18—C17—H17A	109.3
N3—C8—C9	122.00 (15)	C16—C17—H17B	109.3
N3—C8—C7	116.69 (14)	C18—C17—H17B	109.3
C9—C8—C7	121.29 (14)	H17A—C17—H17B	108.0
C10—C9—C8	119.52 (16)	C13—C18—C17	111.29 (14)
C10—C9—H9	120.2	C13—C18—H18A	109.4
C8—C9—H9	120.2	C17—C18—H18A	109.4
C9—C10—C11	118.68 (17)	C13—C18—H18B	109.4
C9—C10—H10	120.7	C17—C18—H18B	109.4
C11—C10—H10	120.7	H18A—C18—H18B	108.0
C12—C11—C10	118.01 (16)	C1—N1—C7	110.47 (12)
C12—C11—H11	121.0	C1—N1—C13	112.17 (12)
C10—C11—H11	121.0	C7—N1—C13	114.30 (12)
N3—C12—C11	124.36 (17)	C2—N2—C6	117.52 (14)
N3—C12—H12	117.8	C8—N3—C12	117.42 (15)
C11—C12—H12	117.8
N1—C1—C2—N2	−142.02 (14)	C15—C16—C17—C18	−55.53 (19)
N1—C1—C2—C3	40.6 (2)	N1—C13—C18—C17	175.48 (13)
N2—C2—C3—C4	−1.6 (2)	C14—C13—C18—C17	−55.51 (17)
C1—C2—C3—C4	175.56 (14)	C16—C17—C18—C13	55.43 (18)
C2—C3—C4—C5	0.6 (2)	C2—C1—N1—C7	−159.59 (13)
C3—C4—C5—C6	0.6 (2)	C2—C1—N1—C13	71.62 (17)
C4—C5—C6—N2	−0.8 (3)	C8—C7—N1—C1	73.28 (16)
N1—C7—C8—N3	−140.81 (14)	C8—C7—N1—C13	−159.09 (13)
N1—C7—C8—C9	40.9 (2)	C18—C13—N1—C1	−159.74 (12)
N3—C8—C9—C10	1.0 (2)	C14—C13—N1—C1	73.93 (15)
C7—C8—C9—C10	179.14 (15)	C18—C13—N1—C7	73.51 (16)
C8—C9—C10—C11	−0.2 (3)	C14—C13—N1—C7	−52.83 (17)
C9—C10—C11—C12	−0.6 (3)	C3—C2—N2—C6	1.4 (2)
C10—C11—C12—N3	0.7 (3)	C1—C2—N2—C6	−175.90 (14)
N1—C13—C14—C15	−176.97 (13)	C5—C6—N2—C2	−0.2 (2)
C18—C13—C14—C15	56.58 (17)	C9—C8—N3—C12	−0.9 (2)
C13—C14—C15—C16	−57.35 (18)	C7—C8—N3—C12	−179.15 (15)
C14—C15—C16—C17	56.55 (19)	C11—C12—N3—C8	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2i	0.95	2.55	3.475 (2)	166 (1)
C11—H11···N2ii	0.95	2.64	3.511 (2)	153 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2i	0.95	2.55	3.475 (2)	166 (1)
C11—H11⋯N2ii	0.95	2.64	3.511 (2)	153 (1)

Symmetry codes: (i) ; (ii) .