organic compounds
4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine
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
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.
CCDC reference: 1480520
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.
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 (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 .
details are summarized in Table 2Structural data
CCDC reference: 1480520
10.1107/S241431461600804X/bt4012sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S241431461600804X/bt4012Isup2.hkl
Supporting information file. DOI: 10.1107/S241431461600804X/bt4012Isup3.cml
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
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).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).
Crystal data, data collection and structure
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 Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) otherwise.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
(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).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
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.Data collection: APEX2 (Bruker, 2006); cell
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).Fig. 1. Molecular structure of the title compound with atom labelling and displacement ellipsoids drawn at the 50% probability level. |
C17H21N3O | F(000) = 608 |
Mr = 283.37 | Dx = 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 |
Bruker SMART CCD diffractometer | 3310 reflections with I > 2σ(I) |
Radiation source: sealed Tube | Rint = 0.024 |
Graphite monochromator | θmax = 28.0°, θmin = 2.5° |
CCD scan | h = −19→19 |
65777 measured reflections | k = −13→13 |
3668 independent reflections | l = −13→13 |
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(Fo2) + (0.067P)2 + 0.4545P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3668 reflections | Δρmax = 0.29 e Å−3 |
192 parameters | Δρmin = −0.25 e Å−3 |
C17H21N3O | V = 1518.47 (16) Å3 |
Mr = 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)° |
Bruker SMART CCD diffractometer | 3310 reflections with I > 2σ(I) |
65777 measured reflections | Rint = 0.024 |
3668 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.29 e Å−3 |
3668 reflections | Δρmin = −0.25 e Å−3 |
192 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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
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