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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Oct 31;64(Pt 11):o2216. doi: 10.1107/S1600536808032327

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

Pierre Koch a, Dieter Schollmeyer b, Stefan Laufer a,*
PMCID: PMC2959623  PMID: 21581073

Abstract

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 ▶).graphic file with name e-64-o2216-scheme1.jpg

Experimental

Crystal data

  • C11H16N2O2

  • M r = 208.26

  • Orthorhombic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.057

  • wR(F 2) = 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

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.

Supplementary Material

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

e-64-o2216-sup1.cif (22.5KB, cif)

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

e-64-o2216-Isup2.hkl (121.4KB, hkl)

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

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
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Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C11H16N2O2 F(000) = 896
Mr = 208.26 Dx = 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
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Data collection

Enraf–Nonius CAD-4 diffractometer Rint = 0.061
Radiation source: rotating anode θmax = 70.0°, θmin = 4.5°
graphite 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%
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Refinement

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(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01 (Δ/σ)max = 0.002
2471 reflections Δρmax = 0.25 e Å−3
280 parameters Δρmin = −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)
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Special details

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

x y z Uiso*/Ueq
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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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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
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2808).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-o2216-sup1.cif (22.5KB, cif)

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

e-64-o2216-Isup2.hkl (121.4KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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