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

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ISSN: 2056-9890

tert-Butyl N-(4-methyl-2-pyrid­yl)­carbamate

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

(Received 6 October 2008; accepted 7 October 2008; online 31 October 2008)

The crystal structure of the title compound, C11H16N2O2, contains two crystallographically independent mol­ecules forming dimers by pairs of inter­molecular N—H⋯N hydrogen bonds. The two mol­ecules are related by a pseudo-twofold axis. The dihedral angle between the pyridine ring and the carbamate plane differs in the two mol­ecules [12.1 (3) and 3.5 (3)°].

Related literature

For the preparation of the title compound, see: Laufer & Koch (2008[Laufer, S. & Koch, P. (2008). Org. Biomol. Chem. 6, 437-439.]); Koch et al. (2008[Koch, P., Bäuerlein, C., Jank, H. & Laufer, S. (2008). J. Med. Chem. 51, 5630-5640.]). For applications of functionalized 2-amino­pyridines, see, for example: Peifer et al. (2006[Peifer, C., Wagner, G. & Laufer, S. (2006). Curr. Top. Med. Chem. 6, 113-149.]); Kuo, DeAngelis et al. (2005[Kuo, G.-H., DeAngelis, A., Emanuel, S., Wang, A., Zhang, Y., Connolly, P. J., Chen, X., Gruninger, R. H., Rugg, C., Fuentes-Pesquera, A., Middleton, S. A., Jolliffe, L. & Murray, W. V. (2005). J. Med. Chem. 48, 4535-4546.]); Kuo, Wang et al. (2005[Kuo, G.-H., Wang, A., Emanuel, S., DeAngelis, A., Zhang, R., Connolly, P. J., Murray, W. V., Gruninger, R. H., Rugg, C., Sechler, J., Fuentes-Pesquera, A., Johnson, D., Middleton, S. A., Jolliffe, L. & Chen, X. (2005). J. Med. Chem. 48, 1886-1900.]); Swahn et al. (2006[Swahn, B.-M., Xue, Y., Arzel, E., Kallin, E., Magnus, A., Plobeck, N. & Viklund, J. (2006). Bioorg. Med. Chem. Lett. 16, 1396-1401.]).

[Scheme 1]

Experimental

Crystal data
  • C11H16N2O2

  • Mr = 208.26

  • Orthorhombic, P 21 21 21

  • a = 10.5850 (6) Å

  • b = 11.6854 (6) Å

  • c = 18.5568 (15) Å

  • V = 2295.3 (3) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.68 mm−1

  • T = 193 (2) K

  • 0.51 × 0.16 × 0.06 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 4711 measured reflections

  • 2471 independent reflections

  • 1782 reflections with I > 2σ(I)

  • Rint = 0.061

  • 3 standard reflections frequency: 60 min intensity decay: 3%

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.149

  • S = 1.01

  • 2471 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N8A—H8A⋯N2B 0.94 2.05 2.980 (5) 171
N8B—H8B⋯N2A 0.98 2.04 3.015 (5) 173

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971[Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

N-substituted 2-aminopyridin-4-yl derivatives can be found in different biological active compounds, like p38 MAP kinase inhibitors (Peifer et al., 2006), VEGFR-2 inhibitors (Kuo, Wang et al., 2005a), CDK inhibitors (Kuo, DeAngelis et al., 2005) or JNK3 inhibitors (Swahn et al., 2006). The title compound, tert-butyl 4-methylpyridin-2-ylcarbamate (I), was synthesized as an intermediate in the synthesis of 2-alkylsulfanyl-5-(2-aminopyridin-4-yl)-4-(4-fluorophenyl)imidazoles as potent p38 MAP kinase inhibitors (Laufer & Koch, 2008; Koch et al., 2008).

The crystal stucture of the title compound I, Fig. 1, contains two crystallographically independent molecules forming dimers by intermolecular N–H···N hydrogen bonds. The two molecules are related by a pseudo 2-fold axis.

As might be expected the pyridine ring as well as the carbamate fragment are planar. The dihedral angle between the pyridine ring and the carbamate plane of molecule A [12.1 (3)°] is bigger than in molecule B [3.5 (3)°].

The N8—C9 is shorter than a normal N—C-bond and longer than a N-C-bond (N8A—C9A: 1.373 (6) Å; N8B—C9B: 1.367 (5) Å), indicating the partially double bond character of the N8—C9-bond of the carbamate.

Related literature top

For the preparation of the title compound, see: Laufer & Koch (2008); Koch et al. (2008). For applications of functionalized 2-aminopyridines, see, for example: Peifer et al. (2006); Kuo, DeAngelis et al. (2005); Kuo, Wang et al. (2005); Swahn et al. (2006).

Experimental top

To a solution of freshly distilled tert-butanol (450 ml) and di-tert-butyl dicarbonate (16.81 g, 77.0 mmol) was added slowly 2-amino-4-methylpyridine (7.57 g, 70.0 mmol). The mixture was stirred at room temperature for 3 d, the solvent was removed in vacuo and the residue was recrystallized from hot 2-propanol, affording 12.30 g (84%) of I as colourless crystals (Laufer & Koch, 2008).

Refinement top

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. H-atom bonded to N were located from a difference Fourier map and constrained to this position. All hydrogen atoms bonded to C were placed at calculated positions with C—H = 0.95 Å (for aromatic C) or 0.98 Å (for sp3 C-atoms) and refined in the riding-model approximation with isotropic displacement parameters set to 1.2 (1.5 for methyl groups) times of the Ueq of the parent atom.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size. Hydrogen bonds are drawn as dashed lines.
tert-Butyl N-(4-methyl-2-pyridyl)carbamate top
Crystal data top
C11H16N2O2F(000) = 896
Mr = 208.26Dx = 1.205 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 10.5850 (6) Åθ = 21–26°
b = 11.6854 (6) ŵ = 0.68 mm1
c = 18.5568 (15) ÅT = 193 K
V = 2295.3 (3) Å3Plate, colourless
Z = 80.51 × 0.16 × 0.06 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.061
Radiation source: rotating anodeθmax = 70.0°, θmin = 4.5°
Graphite monochromatorh = 1212
ω/2θ scansk = 1314
4711 measured reflectionsl = 2222
2471 independent reflections3 standard reflections every 60 min
1782 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
2471 reflectionsΔρmax = 0.25 e Å3
280 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (4)
Crystal data top
C11H16N2O2V = 2295.3 (3) Å3
Mr = 208.26Z = 8
Orthorhombic, P212121Cu Kα radiation
a = 10.5850 (6) ŵ = 0.68 mm1
b = 11.6854 (6) ÅT = 193 K
c = 18.5568 (15) Å0.51 × 0.16 × 0.06 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.061
4711 measured reflections3 standard reflections every 60 min
2471 independent reflections intensity decay: 3%
1782 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.01Δρmax = 0.25 e Å3
2471 reflectionsΔρmin = 0.25 e Å3
280 parameters
Special details top

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. Friedel pairs merged. 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 (Å2) top
xyzUiso*/Ueq
C1A0.0792 (4)0.7774 (3)0.3417 (2)0.0335 (10)
N2A0.1189 (4)0.7180 (3)0.28496 (19)0.0364 (8)
C3A0.0776 (5)0.6104 (4)0.2792 (3)0.0451 (12)
H3A0.10520.56630.23920.054*
C4A0.0032 (5)0.5596 (4)0.3282 (3)0.0462 (12)
H4A0.03090.48300.32150.055*
C5A0.0430 (4)0.6223 (4)0.3872 (3)0.0407 (11)
C6A0.0026 (4)0.7332 (4)0.3947 (2)0.0393 (11)
H6A0.01890.77770.43570.047*
C7A0.1333 (6)0.5727 (5)0.4407 (3)0.0613 (15)
H7A0.10600.49520.45360.092*
H7B0.21800.56960.41950.092*
H7C0.13490.62070.48400.092*
N8A0.1233 (4)0.8913 (3)0.3411 (2)0.0382 (9)
H8A0.17330.91800.30260.046*
C9A0.0976 (4)0.9746 (4)0.3912 (2)0.0379 (11)
O10A0.0460 (4)0.9595 (3)0.44786 (18)0.0545 (10)
O11A0.1393 (3)1.0749 (2)0.36505 (16)0.0373 (7)
C12A0.1276 (4)1.1805 (4)0.4084 (2)0.0370 (10)
C13A0.2094 (5)1.1704 (5)0.4741 (3)0.0490 (12)
H13A0.29641.15360.45950.073*
H13B0.17781.10840.50480.073*
H13C0.20741.24260.50090.073*
C14A0.0098 (5)1.2060 (4)0.4244 (3)0.0497 (13)
H14A0.04401.14660.45620.075*
H14B0.05781.20740.37930.075*
H14C0.01651.28070.44820.075*
C15A0.1797 (5)1.2711 (4)0.3565 (3)0.0512 (13)
H15A0.13131.26940.31150.077*
H15B0.26871.25480.34630.077*
H15C0.17241.34690.37860.077*
C1B0.3724 (4)0.8850 (3)0.1817 (2)0.0294 (9)
N2B0.2977 (4)0.9520 (3)0.2209 (2)0.0382 (9)
C3B0.3289 (5)1.0633 (4)0.2247 (3)0.0447 (12)
H3B0.27601.11290.25180.054*
C4B0.4328 (5)1.1091 (4)0.1916 (2)0.0413 (11)
H4B0.45241.18790.19720.050*
C5B0.5093 (4)1.0392 (4)0.1496 (2)0.0357 (10)
C6B0.4761 (4)0.9242 (4)0.1449 (2)0.0348 (10)
H6B0.52500.87320.11630.042*
C7B0.6208 (5)1.0861 (4)0.1101 (3)0.0491 (12)
H7D0.59751.10070.05980.074*
H7E0.69001.03050.11170.074*
H7F0.64791.15770.13280.074*
N8B0.3330 (4)0.7691 (3)0.18270 (19)0.0336 (8)
H8B0.25920.75670.21350.040*
C9B0.3881 (4)0.6812 (4)0.1456 (2)0.0313 (9)
O10B0.4763 (3)0.6874 (3)0.10641 (17)0.0434 (8)
O11B0.3214 (3)0.5851 (2)0.16178 (16)0.0377 (7)
C12B0.3526 (4)0.4770 (4)0.1243 (3)0.0406 (11)
C13B0.3232 (6)0.4884 (5)0.0454 (3)0.0589 (15)
H13D0.38290.54180.02310.088*
H13E0.23690.51750.03950.088*
H13F0.33040.41340.02210.088*
C14B0.4870 (5)0.4394 (4)0.1387 (3)0.0481 (12)
H14D0.50030.43270.19080.072*
H14E0.54570.49620.11890.072*
H14F0.50210.36510.11580.072*
C15B0.2625 (5)0.3941 (4)0.1610 (4)0.0652 (17)
H15D0.17520.41860.15240.098*
H15E0.27930.39320.21290.098*
H15F0.27490.31710.14120.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.036 (2)0.024 (2)0.040 (2)0.0047 (18)0.0011 (19)0.0019 (19)
N2A0.0373 (19)0.0282 (18)0.0438 (19)0.0015 (16)0.0037 (17)0.0048 (16)
C3A0.045 (3)0.026 (2)0.064 (3)0.003 (2)0.006 (2)0.004 (2)
C4A0.042 (3)0.030 (2)0.067 (3)0.007 (2)0.003 (2)0.008 (2)
C5A0.038 (2)0.034 (2)0.050 (3)0.005 (2)0.005 (2)0.013 (2)
C6A0.042 (3)0.034 (2)0.042 (2)0.002 (2)0.005 (2)0.005 (2)
C7A0.066 (4)0.052 (3)0.066 (3)0.021 (3)0.001 (3)0.017 (3)
N8A0.046 (2)0.0258 (18)0.043 (2)0.0051 (17)0.0153 (19)0.0017 (16)
C9A0.041 (3)0.033 (2)0.039 (2)0.006 (2)0.008 (2)0.0046 (19)
O10A0.076 (3)0.0417 (19)0.0456 (18)0.0087 (19)0.0239 (19)0.0056 (16)
O11A0.0443 (18)0.0245 (15)0.0431 (16)0.0019 (14)0.0098 (14)0.0037 (13)
C12A0.041 (2)0.025 (2)0.045 (2)0.001 (2)0.006 (2)0.011 (2)
C13A0.048 (3)0.048 (3)0.051 (3)0.004 (2)0.003 (2)0.008 (3)
C14A0.040 (3)0.046 (3)0.063 (3)0.007 (2)0.003 (2)0.016 (2)
C15A0.066 (3)0.024 (2)0.063 (3)0.004 (2)0.012 (3)0.005 (2)
C1B0.033 (2)0.0230 (19)0.032 (2)0.0001 (18)0.0006 (18)0.0032 (16)
N2B0.041 (2)0.0272 (18)0.046 (2)0.0003 (16)0.0107 (17)0.0017 (17)
C3B0.055 (3)0.022 (2)0.057 (3)0.003 (2)0.017 (3)0.002 (2)
C4B0.049 (3)0.029 (2)0.046 (3)0.001 (2)0.006 (2)0.001 (2)
C5B0.034 (2)0.036 (2)0.037 (2)0.0042 (19)0.0002 (19)0.0039 (19)
C6B0.038 (2)0.030 (2)0.036 (2)0.004 (2)0.002 (2)0.0007 (18)
C7B0.041 (3)0.045 (3)0.061 (3)0.011 (2)0.010 (2)0.002 (2)
N8B0.0341 (19)0.0244 (17)0.0422 (19)0.0048 (16)0.0077 (16)0.0066 (15)
C9B0.034 (2)0.026 (2)0.033 (2)0.0006 (19)0.0024 (19)0.0018 (18)
O10B0.0500 (19)0.0297 (16)0.0503 (18)0.0016 (15)0.0171 (17)0.0035 (14)
O11B0.0369 (16)0.0251 (15)0.0513 (18)0.0044 (13)0.0061 (15)0.0104 (14)
C12B0.039 (3)0.028 (2)0.055 (3)0.005 (2)0.003 (2)0.011 (2)
C13B0.070 (4)0.047 (3)0.060 (3)0.022 (3)0.016 (3)0.020 (3)
C14B0.047 (3)0.041 (3)0.056 (3)0.001 (2)0.005 (2)0.002 (2)
C15B0.056 (3)0.031 (3)0.108 (5)0.004 (3)0.015 (3)0.016 (3)
Geometric parameters (Å, º) top
C1A—N2A1.330 (5)C1B—N2B1.330 (5)
C1A—C6A1.375 (6)C1B—C6B1.372 (6)
C1A—N8A1.411 (5)C1B—N8B1.418 (5)
N2A—C3A1.336 (5)N2B—C3B1.344 (5)
C3A—C4A1.382 (7)C3B—C4B1.369 (6)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.383 (7)C4B—C5B1.388 (6)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.389 (6)C5B—C6B1.392 (6)
C5A—C7A1.494 (7)C5B—C7B1.494 (6)
C6A—H6A0.9500C6B—H6B0.9500
C7A—H7A0.9800C7B—H7D0.9800
C7A—H7B0.9800C7B—H7E0.9800
C7A—H7C0.9800C7B—H7F0.9800
N8A—C9A1.373 (5)N8B—C9B1.367 (5)
N8A—H8A0.9418N8B—H8B0.9790
C9A—O10A1.199 (5)C9B—O10B1.184 (5)
C9A—O11A1.343 (5)C9B—O11B1.361 (5)
O11A—C12A1.477 (5)O11B—C12B1.479 (5)
C12A—C13A1.500 (6)C12B—C13B1.503 (7)
C12A—C14A1.514 (7)C12B—C14B1.512 (7)
C12A—C15A1.533 (6)C12B—C15B1.520 (7)
C13A—H13A0.9800C13B—H13D0.9800
C13A—H13B0.9800C13B—H13E0.9800
C13A—H13C0.9800C13B—H13F0.9800
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
N2A—C1A—C6A123.8 (4)N2B—C1B—C6B123.6 (4)
N2A—C1A—N8A112.4 (4)N2B—C1B—N8B112.3 (4)
C6A—C1A—N8A123.8 (4)C6B—C1B—N8B124.1 (4)
C1A—N2A—C3A116.8 (4)C1B—N2B—C3B116.8 (4)
N2A—C3A—C4A123.6 (5)N2B—C3B—C4B123.5 (4)
N2A—C3A—H3A118.2N2B—C3B—H3B118.2
C4A—C3A—H3A118.2C4B—C3B—H3B118.2
C3A—C4A—C5A118.8 (4)C3B—C4B—C5B119.3 (4)
C3A—C4A—H4A120.6C3B—C4B—H4B120.3
C5A—C4A—H4A120.6C5B—C4B—H4B120.3
C4A—C5A—C6A117.9 (4)C4B—C5B—C6B117.2 (4)
C4A—C5A—C7A121.0 (4)C4B—C5B—C7B121.4 (4)
C6A—C5A—C7A121.2 (5)C6B—C5B—C7B121.4 (4)
C1A—C6A—C5A119.0 (4)C1B—C6B—C5B119.5 (4)
C1A—C6A—H6A120.5C1B—C6B—H6B120.3
C5A—C6A—H6A120.5C5B—C6B—H6B120.3
C5A—C7A—H7A109.5C5B—C7B—H7D109.5
C5A—C7A—H7B109.5C5B—C7B—H7E109.5
H7A—C7A—H7B109.5H7D—C7B—H7E109.5
C5A—C7A—H7C109.5C5B—C7B—H7F109.5
H7A—C7A—H7C109.5H7D—C7B—H7F109.5
H7B—C7A—H7C109.5H7E—C7B—H7F109.5
C9A—N8A—C1A126.7 (4)C9B—N8B—C1B125.8 (4)
C9A—N8A—H8A113.0C9B—N8B—H8B121.6
C1A—N8A—H8A120.3C1B—N8B—H8B112.5
O10A—C9A—O11A126.5 (4)O10B—C9B—O11B126.5 (4)
O10A—C9A—N8A125.5 (4)O10B—C9B—N8B126.9 (4)
O11A—C9A—N8A108.0 (3)O11B—C9B—N8B106.7 (3)
C9A—O11A—C12A120.3 (3)C9B—O11B—C12B119.0 (3)
O11A—C12A—C13A109.2 (4)O11B—C12B—C13B109.6 (4)
O11A—C12A—C14A110.6 (4)O11B—C12B—C14B112.0 (4)
C13A—C12A—C14A114.2 (4)C13B—C12B—C14B113.2 (4)
O11A—C12A—C15A101.8 (3)O11B—C12B—C15B101.1 (3)
C13A—C12A—C15A110.9 (4)C13B—C12B—C15B111.3 (5)
C14A—C12A—C15A109.4 (4)C14B—C12B—C15B109.0 (4)
C12A—C13A—H13A109.5C12B—C13B—H13D109.5
C12A—C13A—H13B109.5C12B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C12A—C13A—H13C109.5C12B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C12A—C14A—H14A109.5C12B—C14B—H14D109.5
C12A—C14A—H14B109.5C12B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C12A—C14A—H14C109.5C12B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C12A—C15A—H15A109.5C12B—C15B—H15D109.5
C12A—C15A—H15B109.5C12B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C12A—C15A—H15C109.5C12B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C6A—C1A—N2A—C3A2.1 (6)C6B—C1B—N2B—C3B1.2 (7)
N8A—C1A—N2A—C3A177.2 (4)N8B—C1B—N2B—C3B178.6 (4)
C1A—N2A—C3A—C4A0.3 (7)C1B—N2B—C3B—C4B1.0 (8)
N2A—C3A—C4A—C5A0.7 (7)N2B—C3B—C4B—C5B2.2 (8)
C3A—C4A—C5A—C6A1.2 (7)C3B—C4B—C5B—C6B1.2 (7)
C3A—C4A—C5A—C7A178.2 (5)C3B—C4B—C5B—C7B177.6 (5)
N2A—C1A—C6A—C5A4.0 (7)N2B—C1B—C6B—C5B2.0 (7)
N8A—C1A—C6A—C5A175.3 (4)N8B—C1B—C6B—C5B177.7 (4)
C4A—C5A—C6A—C1A3.4 (7)C4B—C5B—C6B—C1B0.8 (6)
C7A—C5A—C6A—C1A176.0 (5)C7B—C5B—C6B—C1B179.5 (4)
N2A—C1A—N8A—C9A178.9 (4)N2B—C1B—N8B—C9B177.5 (4)
C6A—C1A—N8A—C9A0.4 (7)C6B—C1B—N8B—C9B2.7 (7)
C1A—N8A—C9A—O10A9.6 (8)C1B—N8B—C9B—O10B0.7 (7)
C1A—N8A—C9A—O11A169.8 (4)C1B—N8B—C9B—O11B179.9 (4)
O10A—C9A—O11A—C12A2.3 (7)O10B—C9B—O11B—C12B4.7 (6)
N8A—C9A—O11A—C12A178.3 (4)N8B—C9B—O11B—C12B174.8 (3)
C9A—O11A—C12A—C13A65.5 (5)C9B—O11B—C12B—C13B65.3 (5)
C9A—O11A—C12A—C14A61.0 (5)C9B—O11B—C12B—C14B61.2 (5)
C9A—O11A—C12A—C15A177.2 (4)C9B—O11B—C12B—C15B177.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8A—H8A···N2B0.942.052.980 (5)171
N8B—H8B···N2A0.982.043.015 (5)173

Experimental details

Crystal data
Chemical formulaC11H16N2O2
Mr208.26
Crystal system, space groupOrthorhombic, P212121
Temperature (K)193
a, b, c (Å)10.5850 (6), 11.6854 (6), 18.5568 (15)
V3)2295.3 (3)
Z8
Radiation typeCu Kα
µ (mm1)0.68
Crystal size (mm)0.51 × 0.16 × 0.06
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4711, 2471, 1782
Rint0.061
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.149, 1.01
No. of reflections2471
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.25

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8A—H8A···N2B0.942.052.980 (5)170.8
N8B—H8B···N2A0.982.043.015 (5)173.0
 

Acknowledgements

The authors are thankful for financial support from the EU, part of the EU-Craft Programme, Framework Project 6 `MACROCEPT'.

References

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