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

Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536808032327

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2216

doi:10.1107/S1600536808032327

Open

access

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

Pierre Koch,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^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 ); 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

Crystal data

C₁₁H₁₆N₂O₂
M_r = 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)
R_int = 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
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CAD-4 Software; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032327/bt2808sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032327/bt2808Isup2.hkl

checkCIF report

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).

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

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

C₁₁H₁₆N₂O₂	F(000) = 896
M_r = 208.26	D_x = 1.205 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.5850 (6) Å	θ = 21–26°
b = 11.6854 (6) Å	µ = 0.68 mm⁻¹
c = 18.5568 (15) Å	T = 193 K
V = 2295.3 (3) Å³	Plate, colourless
Z = 8	0.51 × 0.16 × 0.06 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.061
Radiation source: rotating anode	θ_max = 70.0°, θ_min = 4.5°
Graphite monochromator	h = −12→12
ω/2θ scans	k = −13→14
4711 measured reflections	l = −22→22
2471 independent reflections	3 standard reflections every 60 min
1782 reflections with I > 2σ(I)	intensity decay: 3%

Refinement top

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0707P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
2471 reflections	Δρ_max = 0.25 e Å⁻³
280 parameters	Δρ_min = −0.25 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: 0.0021 (4)

Crystal data top

C₁₁H₁₆N₂O₂	V = 2295.3 (3) Å³
M_r = 208.26	Z = 8
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 10.5850 (6) Å	µ = 0.68 mm⁻¹
b = 11.6854 (6) Å	T = 193 K
c = 18.5568 (15) Å	0.51 × 0.16 × 0.06 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.061
4711 measured reflections	3 standard reflections every 60 min
2471 independent reflections	intensity decay: 3%
1782 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
2471 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1A	0.0792 (4)	0.7774 (3)	0.3417 (2)	0.0335 (10)
N2A	0.1189 (4)	0.7180 (3)	0.28496 (19)	0.0364 (8)
C3A	0.0776 (5)	0.6104 (4)	0.2792 (3)	0.0451 (12)
H3A	0.1052	0.5663	0.2392	0.054*
C4A	−0.0032 (5)	0.5596 (4)	0.3282 (3)	0.0462 (12)
H4A	−0.0309	0.4830	0.3215	0.055*
C5A	−0.0430 (4)	0.6223 (4)	0.3872 (3)	0.0407 (11)
C6A	0.0026 (4)	0.7332 (4)	0.3947 (2)	0.0393 (11)
H6A	−0.0189	0.7777	0.4357	0.047*
C7A	−0.1333 (6)	0.5727 (5)	0.4407 (3)	0.0613 (15)
H7A	−0.1060	0.4952	0.4536	0.092*
H7B	−0.2180	0.5696	0.4195	0.092*
H7C	−0.1349	0.6207	0.4840	0.092*
N8A	0.1233 (4)	0.8913 (3)	0.3411 (2)	0.0382 (9)
H8A	0.1733	0.9180	0.3026	0.046*
C9A	0.0976 (4)	0.9746 (4)	0.3912 (2)	0.0379 (11)
O10A	0.0460 (4)	0.9595 (3)	0.44786 (18)	0.0545 (10)
O11A	0.1393 (3)	1.0749 (2)	0.36505 (16)	0.0373 (7)
C12A	0.1276 (4)	1.1805 (4)	0.4084 (2)	0.0370 (10)
C13A	0.2094 (5)	1.1704 (5)	0.4741 (3)	0.0490 (12)
H13A	0.2964	1.1536	0.4595	0.073*
H13B	0.1778	1.1084	0.5048	0.073*
H13C	0.2074	1.2426	0.5009	0.073*
C14A	−0.0098 (5)	1.2060 (4)	0.4244 (3)	0.0497 (13)
H14A	−0.0440	1.1466	0.4562	0.075*
H14B	−0.0578	1.2074	0.3793	0.075*
H14C	−0.0165	1.2807	0.4482	0.075*
C15A	0.1797 (5)	1.2711 (4)	0.3565 (3)	0.0512 (13)
H15A	0.1313	1.2694	0.3115	0.077*
H15B	0.2687	1.2548	0.3463	0.077*
H15C	0.1724	1.3469	0.3786	0.077*
C1B	0.3724 (4)	0.8850 (3)	0.1817 (2)	0.0294 (9)
N2B	0.2977 (4)	0.9520 (3)	0.2209 (2)	0.0382 (9)
C3B	0.3289 (5)	1.0633 (4)	0.2247 (3)	0.0447 (12)
H3B	0.2760	1.1129	0.2518	0.054*
C4B	0.4328 (5)	1.1091 (4)	0.1916 (2)	0.0413 (11)
H4B	0.4524	1.1879	0.1972	0.050*
C5B	0.5093 (4)	1.0392 (4)	0.1496 (2)	0.0357 (10)
C6B	0.4761 (4)	0.9242 (4)	0.1449 (2)	0.0348 (10)
H6B	0.5250	0.8732	0.1163	0.042*
C7B	0.6208 (5)	1.0861 (4)	0.1101 (3)	0.0491 (12)
H7D	0.5975	1.1007	0.0598	0.074*
H7E	0.6900	1.0305	0.1117	0.074*
H7F	0.6479	1.1577	0.1328	0.074*
N8B	0.3330 (4)	0.7691 (3)	0.18270 (19)	0.0336 (8)
H8B	0.2592	0.7567	0.2135	0.040*
C9B	0.3881 (4)	0.6812 (4)	0.1456 (2)	0.0313 (9)
O10B	0.4763 (3)	0.6874 (3)	0.10641 (17)	0.0434 (8)
O11B	0.3214 (3)	0.5851 (2)	0.16178 (16)	0.0377 (7)
C12B	0.3526 (4)	0.4770 (4)	0.1243 (3)	0.0406 (11)
C13B	0.3232 (6)	0.4884 (5)	0.0454 (3)	0.0589 (15)
H13D	0.3829	0.5418	0.0231	0.088*
H13E	0.2369	0.5175	0.0395	0.088*
H13F	0.3304	0.4134	0.0221	0.088*
C14B	0.4870 (5)	0.4394 (4)	0.1387 (3)	0.0481 (12)
H14D	0.5003	0.4327	0.1908	0.072*
H14E	0.5457	0.4962	0.1189	0.072*
H14F	0.5021	0.3651	0.1158	0.072*
C15B	0.2625 (5)	0.3941 (4)	0.1610 (4)	0.0652 (17)
H15D	0.1752	0.4186	0.1524	0.098*
H15E	0.2793	0.3932	0.2129	0.098*
H15F	0.2749	0.3171	0.1412	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.036 (2)	0.024 (2)	0.040 (2)	0.0047 (18)	0.0011 (19)	0.0019 (19)
N2A	0.0373 (19)	0.0282 (18)	0.0438 (19)	−0.0015 (16)	0.0037 (17)	−0.0048 (16)
C3A	0.045 (3)	0.026 (2)	0.064 (3)	−0.003 (2)	−0.006 (2)	−0.004 (2)
C4A	0.042 (3)	0.030 (2)	0.067 (3)	−0.007 (2)	−0.003 (2)	0.008 (2)
C5A	0.038 (2)	0.034 (2)	0.050 (3)	−0.005 (2)	−0.005 (2)	0.013 (2)
C6A	0.042 (3)	0.034 (2)	0.042 (2)	0.002 (2)	0.005 (2)	0.005 (2)
C7A	0.066 (4)	0.052 (3)	0.066 (3)	−0.021 (3)	0.001 (3)	0.017 (3)
N8A	0.046 (2)	0.0258 (18)	0.043 (2)	−0.0051 (17)	0.0153 (19)	−0.0017 (16)
C9A	0.041 (3)	0.033 (2)	0.039 (2)	−0.006 (2)	0.008 (2)	−0.0046 (19)
O10A	0.076 (3)	0.0417 (19)	0.0456 (18)	−0.0087 (19)	0.0239 (19)	−0.0056 (16)
O11A	0.0443 (18)	0.0245 (15)	0.0431 (16)	−0.0019 (14)	0.0098 (14)	−0.0037 (13)
C12A	0.041 (2)	0.025 (2)	0.045 (2)	0.001 (2)	0.006 (2)	−0.011 (2)
C13A	0.048 (3)	0.048 (3)	0.051 (3)	0.004 (2)	−0.003 (2)	−0.008 (3)
C14A	0.040 (3)	0.046 (3)	0.063 (3)	0.007 (2)	0.003 (2)	−0.016 (2)
C15A	0.066 (3)	0.024 (2)	0.063 (3)	−0.004 (2)	0.012 (3)	−0.005 (2)
C1B	0.033 (2)	0.0230 (19)	0.032 (2)	0.0001 (18)	0.0006 (18)	−0.0032 (16)
N2B	0.041 (2)	0.0272 (18)	0.046 (2)	−0.0003 (16)	0.0107 (17)	−0.0017 (17)
C3B	0.055 (3)	0.022 (2)	0.057 (3)	0.003 (2)	0.017 (3)	−0.002 (2)
C4B	0.049 (3)	0.029 (2)	0.046 (3)	−0.001 (2)	0.006 (2)	0.001 (2)
C5B	0.034 (2)	0.036 (2)	0.037 (2)	−0.0042 (19)	0.0002 (19)	0.0039 (19)
C6B	0.038 (2)	0.030 (2)	0.036 (2)	0.004 (2)	0.002 (2)	−0.0007 (18)
C7B	0.041 (3)	0.045 (3)	0.061 (3)	−0.011 (2)	0.010 (2)	−0.002 (2)
N8B	0.0341 (19)	0.0244 (17)	0.0422 (19)	−0.0048 (16)	0.0077 (16)	−0.0066 (15)
C9B	0.034 (2)	0.026 (2)	0.033 (2)	0.0006 (19)	0.0024 (19)	−0.0018 (18)
O10B	0.0500 (19)	0.0297 (16)	0.0503 (18)	0.0016 (15)	0.0171 (17)	−0.0035 (14)
O11B	0.0369 (16)	0.0251 (15)	0.0513 (18)	−0.0044 (13)	0.0061 (15)	−0.0104 (14)
C12B	0.039 (3)	0.028 (2)	0.055 (3)	0.005 (2)	−0.003 (2)	−0.011 (2)
C13B	0.070 (4)	0.047 (3)	0.060 (3)	0.022 (3)	−0.016 (3)	−0.020 (3)
C14B	0.047 (3)	0.041 (3)	0.056 (3)	0.001 (2)	−0.005 (2)	−0.002 (2)
C15B	0.056 (3)	0.031 (3)	0.108 (5)	−0.004 (3)	0.015 (3)	−0.016 (3)

Geometric parameters (Å, º) top

C1A—N2A	1.330 (5)	C1B—N2B	1.330 (5)
C1A—C6A	1.375 (6)	C1B—C6B	1.372 (6)
C1A—N8A	1.411 (5)	C1B—N8B	1.418 (5)
N2A—C3A	1.336 (5)	N2B—C3B	1.344 (5)
C3A—C4A	1.382 (7)	C3B—C4B	1.369 (6)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.383 (7)	C4B—C5B	1.388 (6)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.389 (6)	C5B—C6B	1.392 (6)
C5A—C7A	1.494 (7)	C5B—C7B	1.494 (6)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—H7A	0.9800	C7B—H7D	0.9800
C7A—H7B	0.9800	C7B—H7E	0.9800
C7A—H7C	0.9800	C7B—H7F	0.9800
N8A—C9A	1.373 (5)	N8B—C9B	1.367 (5)
N8A—H8A	0.9418	N8B—H8B	0.9790
C9A—O10A	1.199 (5)	C9B—O10B	1.184 (5)
C9A—O11A	1.343 (5)	C9B—O11B	1.361 (5)
O11A—C12A	1.477 (5)	O11B—C12B	1.479 (5)
C12A—C13A	1.500 (6)	C12B—C13B	1.503 (7)
C12A—C14A	1.514 (7)	C12B—C14B	1.512 (7)
C12A—C15A	1.533 (6)	C12B—C15B	1.520 (7)
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13B	0.9800	C13B—H13E	0.9800
C13A—H13C	0.9800	C13B—H13F	0.9800
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800

N2A—C1A—C6A	123.8 (4)	N2B—C1B—C6B	123.6 (4)
N2A—C1A—N8A	112.4 (4)	N2B—C1B—N8B	112.3 (4)
C6A—C1A—N8A	123.8 (4)	C6B—C1B—N8B	124.1 (4)
C1A—N2A—C3A	116.8 (4)	C1B—N2B—C3B	116.8 (4)
N2A—C3A—C4A	123.6 (5)	N2B—C3B—C4B	123.5 (4)
N2A—C3A—H3A	118.2	N2B—C3B—H3B	118.2
C4A—C3A—H3A	118.2	C4B—C3B—H3B	118.2
C3A—C4A—C5A	118.8 (4)	C3B—C4B—C5B	119.3 (4)
C3A—C4A—H4A	120.6	C3B—C4B—H4B	120.3
C5A—C4A—H4A	120.6	C5B—C4B—H4B	120.3
C4A—C5A—C6A	117.9 (4)	C4B—C5B—C6B	117.2 (4)
C4A—C5A—C7A	121.0 (4)	C4B—C5B—C7B	121.4 (4)
C6A—C5A—C7A	121.2 (5)	C6B—C5B—C7B	121.4 (4)
C1A—C6A—C5A	119.0 (4)	C1B—C6B—C5B	119.5 (4)
C1A—C6A—H6A	120.5	C1B—C6B—H6B	120.3
C5A—C6A—H6A	120.5	C5B—C6B—H6B	120.3
C5A—C7A—H7A	109.5	C5B—C7B—H7D	109.5
C5A—C7A—H7B	109.5	C5B—C7B—H7E	109.5
H7A—C7A—H7B	109.5	H7D—C7B—H7E	109.5
C5A—C7A—H7C	109.5	C5B—C7B—H7F	109.5
H7A—C7A—H7C	109.5	H7D—C7B—H7F	109.5
H7B—C7A—H7C	109.5	H7E—C7B—H7F	109.5
C9A—N8A—C1A	126.7 (4)	C9B—N8B—C1B	125.8 (4)
C9A—N8A—H8A	113.0	C9B—N8B—H8B	121.6
C1A—N8A—H8A	120.3	C1B—N8B—H8B	112.5
O10A—C9A—O11A	126.5 (4)	O10B—C9B—O11B	126.5 (4)
O10A—C9A—N8A	125.5 (4)	O10B—C9B—N8B	126.9 (4)
O11A—C9A—N8A	108.0 (3)	O11B—C9B—N8B	106.7 (3)
C9A—O11A—C12A	120.3 (3)	C9B—O11B—C12B	119.0 (3)
O11A—C12A—C13A	109.2 (4)	O11B—C12B—C13B	109.6 (4)
O11A—C12A—C14A	110.6 (4)	O11B—C12B—C14B	112.0 (4)
C13A—C12A—C14A	114.2 (4)	C13B—C12B—C14B	113.2 (4)
O11A—C12A—C15A	101.8 (3)	O11B—C12B—C15B	101.1 (3)
C13A—C12A—C15A	110.9 (4)	C13B—C12B—C15B	111.3 (5)
C14A—C12A—C15A	109.4 (4)	C14B—C12B—C15B	109.0 (4)
C12A—C13A—H13A	109.5	C12B—C13B—H13D	109.5
C12A—C13A—H13B	109.5	C12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C12A—C13A—H13C	109.5	C12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C12A—C14A—H14A	109.5	C12B—C14B—H14D	109.5
C12A—C14A—H14B	109.5	C12B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C12A—C14A—H14C	109.5	C12B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C12A—C15A—H15A	109.5	C12B—C15B—H15D	109.5
C12A—C15A—H15B	109.5	C12B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C12A—C15A—H15C	109.5	C12B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5

C6A—C1A—N2A—C3A	2.1 (6)	C6B—C1B—N2B—C3B	−1.2 (7)
N8A—C1A—N2A—C3A	−177.2 (4)	N8B—C1B—N2B—C3B	178.6 (4)
C1A—N2A—C3A—C4A	0.3 (7)	C1B—N2B—C3B—C4B	−1.0 (8)
N2A—C3A—C4A—C5A	−0.7 (7)	N2B—C3B—C4B—C5B	2.2 (8)
C3A—C4A—C5A—C6A	−1.2 (7)	C3B—C4B—C5B—C6B	−1.2 (7)
C3A—C4A—C5A—C7A	178.2 (5)	C3B—C4B—C5B—C7B	177.6 (5)
N2A—C1A—C6A—C5A	−4.0 (7)	N2B—C1B—C6B—C5B	2.0 (7)
N8A—C1A—C6A—C5A	175.3 (4)	N8B—C1B—C6B—C5B	−177.7 (4)
C4A—C5A—C6A—C1A	3.4 (7)	C4B—C5B—C6B—C1B	−0.8 (6)
C7A—C5A—C6A—C1A	−176.0 (5)	C7B—C5B—C6B—C1B	−179.5 (4)
N2A—C1A—N8A—C9A	178.9 (4)	N2B—C1B—N8B—C9B	177.5 (4)
C6A—C1A—N8A—C9A	−0.4 (7)	C6B—C1B—N8B—C9B	−2.7 (7)
C1A—N8A—C9A—O10A	9.6 (8)	C1B—N8B—C9B—O10B	−0.7 (7)
C1A—N8A—C9A—O11A	−169.8 (4)	C1B—N8B—C9B—O11B	179.9 (4)
O10A—C9A—O11A—C12A	2.3 (7)	O10B—C9B—O11B—C12B	−4.7 (6)
N8A—C9A—O11A—C12A	−178.3 (4)	N8B—C9B—O11B—C12B	174.8 (3)
C9A—O11A—C12A—C13A	65.5 (5)	C9B—O11B—C12B—C13B	−65.3 (5)
C9A—O11A—C12A—C14A	−61.0 (5)	C9B—O11B—C12B—C14B	61.2 (5)
C9A—O11A—C12A—C15A	−177.2 (4)	C9B—O11B—C12B—C15B	177.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₆N₂O₂
M_r	208.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	193
a, b, c (Å)	10.5850 (6), 11.6854 (6), 18.5568 (15)
V (Å³)	2295.3 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.51 × 0.16 × 0.06

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4711, 2471, 1782
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.149, 1.01
No. of reflections	2471
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N8A—H8A···N2B	0.94	2.05	2.980 (5)	170.8
N8B—H8B···N2A	0.98	2.04	3.015 (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

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
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. 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
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. Web of Science CrossRef PubMed CAS Google Scholar
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. 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
Peifer, C., Wagner, G. & Laufer, S. (2006). Curr. Top. Med. Chem. 6, 113–149. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swahn, B.-M., Xue, Y., Arzel, E., Kallin, E., Magnus, A., Plobeck, N. & Viklund, J. (2006). Bioorg. Med. Chem. Lett. 16, 1396–1401. Web of Science CrossRef Google Scholar