4-Methyl-N-(4-methyl­pyridin-2-yl)-N-(3,4,5,6-tetra­hydro-2H-pyran-4-yl)pyridin-2-amine

El-Gokha, A.; Schollmeyer, D.; Koch, P.

doi:10.1107/S241431461600804X

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160804

doi:10.1107/S241431461600804X

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4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine

Ahmed El-Gokha,^a Dieter Schollmeyer ^b and Pierre Koch ^a ^*

^aInstitute of Pharmaceutical Sciences, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: pierre.koch@uni-tuebingen.de

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 14 May 2016; accepted 17 May 2016; online 20 May 2016)

In the title compound, C₁₇H₂₁N₃O, the pyridine rings make a dihedral angle of 84.44 (5)°. In the crystal, a C—H⋯N interaction forms a chain of molecules propagating along the twofold screw axis.

Keywords: crystal structure; pyridinamine; tertiary amine; palladium-catalysed arylamination.

CCDC reference: 1480520

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Chemical scheme

Structure description

The title compound was obtained as a side product in the palladium-catalysed reaction of 2-bromo-4-methylpyridine and tetrahydro-2H-pyran-4-amine hydrochloride (Laufer & Koch, 2008 ; Koch et al., 2008 ). The title compound is shown in Fig. 1. One pyridine ring is nearly perpendicular to the other pyridine ring, the dihedral angle between them being 84.44 (5)°. The molecular conformation features a short intramolecular C—H⋯N contact (Table 1). In the crystal, an intermolecular interaction between H14B and N16 forms a chain of molecules along the twofold screw axis.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N9	1.00	2.33	2.7852 (13)	107
C14—H14B⋯N16ⁱ	0.98	2.61	3.4881 (16)	149
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
Molecular structure of the title compound with atom labelling and displacement ellipsoids drawn at the 50% probability level.

Synthesis and crystallization

2-Bromo-4-methylpyridine (0.20 g, 1.2 mmol), tetrahydro-2H-pyran-4-amine hydrochloride (0.19 g, 1.4 mmol), t-BuONa (0.27 g, 2.8 mmol), Pd₂(dba)₃ (21 mg, 0.023 mmol) and BINAP (29 mg, 0.046 mmol) were dissolved in dry toluene (30 ml) under an argon atmosphere. The mixture was stirred 2 h at 343 K. The mixture was allowed to cool to 298 K before n-hexane was added. The formed precipitate was filtered off and the filtrate concentrated to dryness. Once again, n-hexane was added to the residue and the precipitate was filtered off. The filtrate was concentrated in vacuo and the crude product was purified by flash chromatography (SiO₂, from n-hexane/EtOAc 1:1 to EtOAc 100%) to afford 20 mg of the title compound as a colorless solid. Suitable crystals for X-ray diffraction were obtained by slow evaporation at 298 K of a solution of n-hexane–ethyl acetate (1:1).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃O
M_r	283.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.5487 (9), 10.1675 (6), 10.4269 (6)
β (°)	100.1035 (17)
V (Å³)	1518.47 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.40 × 0.24

Data collection
Diffractometer	Bruker SMART CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	65777, 3668, 3310
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.122, 1.05
No. of reflections	3668
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25
Computer programs: APEX2 (Bruker, 2006 ), SIR97 (Altomare et al., 1999 ), SHELXL2014 and XP (Sheldrick, 2015 ).

Structural data

CCDC reference: 1480520

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S241431461600804X/bt4012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S241431461600804X/bt4012Isup2.hkl

Supporting information file. DOI: 10.1107/S241431461600804X/bt4012Isup3.cml

checkCIF report

Structural commentary top

The title compound, 4-methyl-N-(4-methylpyridin-2-yl)-N-(tetrahydro-2H- pyran-4-yl)-pyridin-2-amine (I), was obtained as a side product in the palladium-catalyzed reaction of 2-bromo-4-methylpyridine and tetrahydro-2H-pyran-4-amine hydrochloride (Laufer & Koch 2008, Koch et al. 2008).

The analysis of the crystal structure of compound I is shown in Figure 1. One pyridine ring is nearly perpendicular to the other pyridine ring, the dihedral angles between them is 84.44 (5)°. The conformation is stabilized by an Intramolecular hydrogen bond (C2–H2···N9 2.33Å). An intermolecular interaction between H14B and N16 forms a chain of molecules along the twofold screw axis (C14–H14B···N16 2.61Å).

Synthesis and crystallization top

2-Bromo-4-methylpyridine (0.20 g, 1.2 mmol), tetrahydro-2H-pyran-4-amine hydrochloride (0.19 g, 1.4 mmol), t-BuONa (0.27 g, 2.8 mmol), Pd₂(dba)₃ (21 mg, 0.023 mmol), BINAP (29 mg, 0.046 mmol), and toluene (30 mL) were dissolved in dry toluene under argon atmosphere. The mixture was stirred 2 h at 343 K. The mixture was allowed to cool to room temperature before n-hexane was added. The formed precipitate was filtered off and the filtrate concentrated to dryness. Once again, n-hexane was added to the residue and the precipitate was filtered off. The filtrate was concentrated in vacuo and the crude product was purified by flash-chromatography (SiO₂, from n-hexane/EtOAc 1:1 to EtOAc 100%) to afford 20 mg of of I as a colorless solid. Suitable crystals of compound I for X-ray were obtained by slow evaporation at 298 K of a solution of n-hexane - ethyl acetate (1-1).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Nevertheless, they were ideally positioned and refined as riding on their parent atoms, with aromatic C—H = 0.95 Å, tertiary C—H = 1.00 Å, methylene C—H = 0.99 Å and methyl C—H = 0.98 Å, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) otherwise.

Related literature top

For preparation of the title compound, see: Koch et al. (2008).

Experimental top

Structure description top

The title compound was obtained as a side product in the palladium-catalysed reaction of 2-bromo-4-methylpyridine and tetrahydro-2H-pyran-4-amine hydrochloride (Laufer & Koch, 2008; Koch et al., 2008). The title compound is shown in Fig. 1. One pyridine ring is nearly perpendicular to the other pyridine ring, the dihedral angle between them being 84.44 (5)°. The molecular conformation is stabilized by an intramolecular C—H···N hydrogen bond (Table 1). In the crystal, an intermolecular interaction between H14B and N16 forms a chain of molecules along the twofold screw axis.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

Fig. 1. Molecular structure of the title compound with atom labelling and displacement ellipsoids drawn at the 50% probability level.

4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine top

Crystal data top

C₁₇H₂₁N₃O	F(000) = 608
M_r = 283.37	D_x = 1.240 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
a = 14.5487 (9) Å	Cell parameters from 9759 reflections
b = 10.1675 (6) Å	θ = 2.2–36.2°
c = 10.4269 (6) Å	µ = 0.08 mm⁻¹
β = 100.1035 (17)°	T = 173 K
V = 1518.47 (16) Å³	Block, colorless
Z = 4	0.50 × 0.40 × 0.24 mm

Data collection top

Bruker SMART CCD diffractometer	3310 reflections with I > 2σ(I)
Radiation source: sealed Tube	R_int = 0.024
Graphite monochromator	θ_max = 28.0°, θ_min = 2.5°
CCD scan	h = −19→19
65777 measured reflections	k = −13→13
3668 independent reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.067P)² + 0.4545P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3668 reflections	Δρ_max = 0.29 e Å⁻³
192 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₂₁N₃O	V = 1518.47 (16) Å³
M_r = 283.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5487 (9) Å	µ = 0.08 mm⁻¹
b = 10.1675 (6) Å	T = 173 K
c = 10.4269 (6) Å	0.50 × 0.40 × 0.24 mm
β = 100.1035 (17)°

Data collection top

Bruker SMART CCD diffractometer	3310 reflections with I > 2σ(I)
65777 measured reflections	R_int = 0.024
3668 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
3668 reflections	Δρ_min = −0.25 e Å⁻³
192 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.24545 (6)	0.35573 (9)	0.11326 (9)	0.0270 (2)
C2	0.18456 (7)	0.35008 (10)	−0.01542 (9)	0.0240 (2)
H2	0.2066	0.2757	−0.0650	0.029*
C3	0.19032 (8)	0.47553 (11)	−0.09352 (11)	0.0311 (2)
H3A	0.1747	0.5522	−0.0429	0.037*
H3B	0.2548	0.4872	−0.1100	0.037*
C4	0.12302 (9)	0.46855 (13)	−0.22235 (11)	0.0363 (3)
H4A	0.1263	0.5517	−0.2707	0.044*
H4B	0.1421	0.3961	−0.2755	0.044*
O5	0.02931 (6)	0.44727 (9)	−0.20449 (8)	0.0362 (2)
C6	0.02138 (8)	0.32609 (13)	−0.13960 (12)	0.0370 (3)
H6A	0.0397	0.2532	−0.1928	0.044*
H6B	−0.0445	0.3122	−0.1305	0.044*
C7	0.08279 (7)	0.32332 (12)	−0.00489 (11)	0.0323 (2)
H7A	0.0778	0.2362	0.0357	0.039*
H7B	0.0609	0.3908	0.0513	0.039*
C8	0.30513 (6)	0.25363 (9)	0.15970 (9)	0.0215 (2)
N9	0.30153 (6)	0.14462 (8)	0.08667 (8)	0.02608 (19)
C10	0.36135 (8)	0.04730 (10)	0.13208 (11)	0.0319 (2)
H10	0.3605	−0.0296	0.0802	0.038*
C11	0.42372 (8)	0.05082 (11)	0.24818 (11)	0.0319 (2)
H11	0.4648	−0.0207	0.2742	0.038*
C12	0.42478 (7)	0.16324 (10)	0.32680 (10)	0.0258 (2)
C13	0.36555 (7)	0.26533 (10)	0.28109 (9)	0.0238 (2)
H13	0.3654	0.3434	0.3311	0.029*
C14	0.48623 (8)	0.17290 (13)	0.45881 (11)	0.0359 (3)
H14A	0.5002	0.2655	0.4798	0.054*
H14B	0.5445	0.1250	0.4577	0.054*
H14C	0.4539	0.1345	0.5247	0.054*
C15	0.25355 (7)	0.47598 (10)	0.18586 (10)	0.0244 (2)
N16	0.32140 (7)	0.55840 (10)	0.16619 (10)	0.0332 (2)
C17	0.33256 (8)	0.66720 (12)	0.23981 (13)	0.0370 (3)
H17	0.3802	0.7272	0.2273	0.044*
C18	0.27875 (8)	0.69742 (11)	0.33315 (12)	0.0331 (2)
H18	0.2903	0.7755	0.3835	0.040*
C19	0.20782 (7)	0.61220 (11)	0.35218 (10)	0.0283 (2)
C20	0.19537 (7)	0.49906 (10)	0.27543 (10)	0.0257 (2)
H20	0.1474	0.4383	0.2845	0.031*
C21	0.14761 (10)	0.63831 (15)	0.45276 (12)	0.0435 (3)
H21A	0.1839	0.6861	0.5263	0.065*
H21B	0.1261	0.5546	0.4835	0.065*
H21C	0.0935	0.6913	0.4140	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0261 (4)	0.0235 (4)	0.0280 (4)	0.0056 (3)	−0.0045 (3)	−0.0052 (3)
C2	0.0229 (4)	0.0240 (5)	0.0235 (5)	0.0033 (3)	−0.0005 (3)	−0.0016 (3)
C3	0.0308 (5)	0.0327 (5)	0.0297 (5)	−0.0025 (4)	0.0051 (4)	0.0041 (4)
C4	0.0387 (6)	0.0449 (7)	0.0254 (5)	0.0034 (5)	0.0064 (4)	0.0071 (4)
O5	0.0315 (4)	0.0450 (5)	0.0302 (4)	0.0100 (3)	−0.0001 (3)	0.0081 (3)
C6	0.0265 (5)	0.0471 (7)	0.0341 (6)	−0.0024 (5)	−0.0043 (4)	0.0072 (5)
C7	0.0255 (5)	0.0410 (6)	0.0284 (5)	−0.0032 (4)	−0.0007 (4)	0.0091 (4)
C8	0.0192 (4)	0.0224 (4)	0.0232 (4)	0.0003 (3)	0.0042 (3)	0.0007 (3)
N9	0.0285 (4)	0.0227 (4)	0.0257 (4)	0.0018 (3)	0.0014 (3)	−0.0017 (3)
C10	0.0390 (6)	0.0234 (5)	0.0316 (5)	0.0059 (4)	0.0016 (4)	−0.0031 (4)
C11	0.0356 (6)	0.0265 (5)	0.0316 (5)	0.0094 (4)	0.0009 (4)	0.0021 (4)
C12	0.0238 (5)	0.0289 (5)	0.0242 (5)	0.0023 (4)	0.0033 (4)	0.0022 (4)
C13	0.0225 (4)	0.0251 (5)	0.0233 (4)	0.0013 (4)	0.0029 (3)	−0.0020 (3)
C14	0.0350 (6)	0.0417 (6)	0.0275 (5)	0.0114 (5)	−0.0039 (4)	−0.0008 (4)
C15	0.0226 (4)	0.0222 (5)	0.0261 (5)	0.0044 (3)	−0.0017 (3)	−0.0020 (3)
N16	0.0286 (4)	0.0319 (5)	0.0398 (5)	−0.0025 (4)	0.0078 (4)	−0.0081 (4)
C17	0.0331 (6)	0.0301 (6)	0.0482 (7)	−0.0065 (4)	0.0087 (5)	−0.0080 (5)
C18	0.0349 (6)	0.0254 (5)	0.0368 (6)	0.0023 (4)	0.0003 (4)	−0.0087 (4)
C19	0.0290 (5)	0.0304 (5)	0.0239 (5)	0.0072 (4)	0.0001 (4)	−0.0021 (4)
C20	0.0250 (5)	0.0257 (5)	0.0247 (5)	0.0013 (4)	0.0001 (4)	0.0011 (4)
C21	0.0454 (7)	0.0548 (8)	0.0320 (6)	0.0017 (6)	0.0115 (5)	−0.0107 (5)

Geometric parameters (Å, º) top

N1—C8	1.3850 (12)	C10—H10	0.9500
N1—C15	1.4319 (12)	C11—C12	1.4051 (15)
N1—C2	1.4736 (12)	C11—H11	0.9500
C2—C3	1.5236 (14)	C12—C13	1.3796 (14)
C2—C7	1.5281 (14)	C12—C14	1.5072 (14)
C2—H2	1.0000	C13—H13	0.9500
C3—C4	1.5188 (15)	C14—H14A	0.9800
C3—H3A	0.9900	C14—H14B	0.9800
C3—H3B	0.9900	C14—H14C	0.9800
C4—O5	1.4245 (15)	C15—N16	1.3379 (14)
C4—H4A	0.9900	C15—C20	1.3861 (14)
C4—H4B	0.9900	N16—C17	1.3400 (15)
O5—C6	1.4201 (15)	C17—C18	1.3863 (17)
C6—C7	1.5269 (15)	C17—H17	0.9500
C6—H6A	0.9900	C18—C19	1.3882 (16)
C6—H6B	0.9900	C18—H18	0.9500
C7—H7A	0.9900	C19—C20	1.3948 (14)
C7—H7B	0.9900	C19—C21	1.5034 (15)
C8—N9	1.3406 (12)	C20—H20	0.9500
C8—C13	1.4137 (13)	C21—H21A	0.9800
N9—C10	1.3476 (14)	C21—H21B	0.9800
C10—C11	1.3801 (15)	C21—H21C	0.9800

C8—N1—C15	117.82 (8)	N9—C10—H10	117.5
C8—N1—C2	121.94 (8)	C11—C10—H10	117.5
C15—N1—C2	119.68 (8)	C10—C11—C12	118.11 (9)
N1—C2—C3	111.92 (8)	C10—C11—H11	120.9
N1—C2—C7	112.14 (8)	C12—C11—H11	120.9
C3—C2—C7	109.41 (8)	C13—C12—C11	117.92 (9)
N1—C2—H2	107.7	C13—C12—C14	120.06 (9)
C3—C2—H2	107.7	C11—C12—C14	122.00 (9)
C7—C2—H2	107.7	C12—C13—C8	119.91 (9)
C4—C3—C2	110.25 (9)	C12—C13—H13	120.0
C4—C3—H3A	109.6	C8—C13—H13	120.0
C2—C3—H3A	109.6	C12—C14—H14A	109.5
C4—C3—H3B	109.6	C12—C14—H14B	109.5
C2—C3—H3B	109.6	H14A—C14—H14B	109.5
H3A—C3—H3B	108.1	C12—C14—H14C	109.5
O5—C4—C3	112.01 (9)	H14A—C14—H14C	109.5
O5—C4—H4A	109.2	H14B—C14—H14C	109.5
C3—C4—H4A	109.2	N16—C15—C20	123.47 (9)
O5—C4—H4B	109.2	N16—C15—N1	116.64 (9)
C3—C4—H4B	109.2	C20—C15—N1	119.83 (9)
H4A—C4—H4B	107.9	C15—N16—C17	116.60 (10)
C6—O5—C4	110.71 (9)	N16—C17—C18	123.96 (11)
O5—C6—C7	111.78 (10)	N16—C17—H17	118.0
O5—C6—H6A	109.3	C18—C17—H17	118.0
C7—C6—H6A	109.3	C17—C18—C19	119.18 (10)
O5—C6—H6B	109.3	C17—C18—H18	120.4
C7—C6—H6B	109.3	C19—C18—H18	120.4
H6A—C6—H6B	107.9	C18—C19—C20	117.24 (10)
C6—C7—C2	110.40 (9)	C18—C19—C21	121.89 (10)
C6—C7—H7A	109.6	C20—C19—C21	120.86 (10)
C2—C7—H7A	109.6	C15—C20—C19	119.54 (10)
C6—C7—H7B	109.6	C15—C20—H20	120.2
C2—C7—H7B	109.6	C19—C20—H20	120.2
H7A—C7—H7B	108.1	C19—C21—H21A	109.5
N9—C8—N1	117.48 (8)	C19—C21—H21B	109.5
N9—C8—C13	122.30 (9)	H21A—C21—H21B	109.5
N1—C8—C13	120.21 (9)	C19—C21—H21C	109.5
C8—N9—C10	116.68 (9)	H21A—C21—H21C	109.5
N9—C10—C11	125.02 (10)	H21B—C21—H21C	109.5

C8—N1—C2—C3	−132.02 (10)	C10—C11—C12—C13	−2.15 (16)
C15—N1—C2—C3	39.22 (13)	C10—C11—C12—C14	176.26 (11)
C8—N1—C2—C7	104.59 (11)	C11—C12—C13—C8	1.15 (15)
C15—N1—C2—C7	−84.18 (12)	C14—C12—C13—C8	−177.30 (9)
N1—C2—C3—C4	−177.13 (8)	N9—C8—C13—C12	1.28 (15)
C7—C2—C3—C4	−52.21 (12)	N1—C8—C13—C12	179.97 (9)
C2—C3—C4—O5	57.26 (13)	C8—N1—C15—N16	81.25 (12)
C3—C4—O5—C6	−61.05 (13)	C2—N1—C15—N16	−90.35 (11)
C4—O5—C6—C7	60.54 (13)	C8—N1—C15—C20	−95.89 (11)
O5—C6—C7—C2	−56.63 (13)	C2—N1—C15—C20	92.52 (12)
N1—C2—C7—C6	176.76 (9)	C20—C15—N16—C17	0.90 (16)
C3—C2—C7—C6	51.96 (12)	N1—C15—N16—C17	−176.12 (10)
C15—N1—C8—N9	−175.55 (9)	C15—N16—C17—C18	0.18 (18)
C2—N1—C8—N9	−4.16 (14)	N16—C17—C18—C19	−0.85 (19)
C15—N1—C8—C13	5.70 (14)	C17—C18—C19—C20	0.44 (16)
C2—N1—C8—C13	177.09 (9)	C17—C18—C19—C21	179.31 (11)
N1—C8—N9—C10	178.73 (9)	N16—C15—C20—C19	−1.29 (15)
C13—C8—N9—C10	−2.55 (14)	N1—C15—C20—C19	175.64 (9)
C8—N9—C10—C11	1.48 (17)	C18—C19—C20—C15	0.55 (14)
N9—C10—C11—C12	0.88 (18)	C21—C19—C20—C15	−178.33 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N9	1.00	2.33	2.7852 (13)	107
C14—H14B···N16ⁱ	0.98	2.61	3.4881 (16)	149

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N9	1.00	2.33	2.7852 (13)	107
C14—H14B···N16ⁱ	0.98	2.61	3.4881 (16)	149

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃O
M_r	283.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.5487 (9), 10.1675 (6), 10.4269 (6)
β (°)	100.1035 (17)
V (Å³)	1518.47 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.40 × 0.24

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	65777, 3668, 3310
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.122, 1.05
No. of reflections	3668
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25

Computer programs: APEX2 (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL2014 (Sheldrick, 2015), XP (Sheldrick, 2015).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Koch, P., Bäuerlein, C., Jank, H. & Laufer, S. (2008). J. Med. Chem. 51, 5630–5640. Web of Science CrossRef PubMed CAS Google Scholar
Laufer, S. & Koch, P. (2008). Org. Biomol. Chem. 6, 437–439. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160804

doi:10.1107/S241431461600804X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Methyl-N-(4-methyl­pyridin-2-yl)-N-(3,4,5,6-tetra­hydro-2H-pyran-4-yl)pyridin-2-amine

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine