5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)meth­yl]-5H-dibenzo[b,f]azepine

B C Manjunath; K S Vinay Kumar; S Madan Kumar; M P Sadashiva; N K Lokanath

doi:10.1107/S1600536813018412

. 2013 Jul 10;69(Pt 8):o1233. doi: 10.1107/S1600536813018412

5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)methyl]-5H-dibenzo[b,f]azepine

B C Manjunath ^a, K S Vinay Kumar ^b, S Madan Kumar ^a, M P Sadashiva ^b, N K Lokanath ^a,^*

PMCID: PMC3793737 PMID: 24109324

Abstract

In the title compound, C₂₄H₂₀N₄, the azepine ring adopts a boat conformation and the dihedral angle between the benzene rings fused to it is 57.95 (8)°. The bond-angle sum at the azepine N atom is 346.6°, indicating a significant deviation from planarity. The triazole ring subtends a dihedral angle of 71.45 (10)° with the terminal phenyl group. A weak intramolecular C—H⋯N_a (a = azepine) interaction occurs, which closes an S(6) ring.

Related literature

For a related structure and background to isoxazole derivatives, see: Abdoh et al. (2013 ▶). graphic file with name e-69-o1233-scheme1.jpg

Experimental

Crystal data

C₂₄H₂₀N₄
M _r = 364.44
Monoclinic,
a = 9.4394 (10) Å
b = 22.206 (3) Å
c = 9.4330 (9) Å
β = 107.172 (3)°
V = 1889.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 300 K
0.26 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
22703 measured reflections
3711 independent reflections
2982 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.124
S = 1.01
3711 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018412/hb7099sup1.cif

e-69-o1233-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018412/hb7099Isup2.hkl

e-69-o1233-Isup2.hkl^{(182KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813018412/hb7099Isup3.cml

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
C7—H7A⋯N4	0.97	2.56	3.173 (2)	121

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Acknowledgments

We thank Professor T. N. Guru Row and Vijith Kumar, SSCU, IISc, Bangalore, India, for providing facilities for the data collection.

supplementary crystallographic information

Comment

The title compound was synthesized, crystallized and its crystal structure is presented as part of our investigations on isoxazole derivatives (Abdoh, et al.,, 2013)

In the title molecule (Fig. 1.) benzene rings fused to azepine rings are nearly planar and its geometry is similar to 5-(Prop-2–1-yl)-5H-dibenzo[b,f]azepine: orthorhombic polymorph. Seven-membered azepine ring adopts a boat conformation as indicated by the puckering parameters Q₂ = 0.7392 (16) Å, Q₃ = 0.2157 (15) Å, φ₂ = 178.44 (12) °, φ₃ = 178.4 (4) °, and the total puckering amplitude, Q_T = 0.7700 (15) Å. The title molecule adopts butterfly shape. The dihedral angle between triazole moiety and benzene ring (C1/C2/C3/C4/C5/C6) is 71.45 (10)°. The packing of molecules is shown in the figure 2.

Experimental

5-(prop-2-yn-1-yl)-5H-dibenzo[b,f]azepine (2.1 mmol) was taken in a mixture of dichloromethane and water in the ratio 1:1, cuprous iodide (0.21 mmol) was added followed by sodium ascorbate (0.21 mmol) at room temperature. After 10 minutes, benzyl azide was added (2.3 mmol) at room temperature. Then, the resulting reaction mixture was allowed for stirring upto 6 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 x 20 ml), the combined ethyl acetate layer was washed with brine solution (2 x 25 ml). Then, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude, which was purified by column chromatography over silica gel (60–120 mesh) using Hexane: Ethyl acetate mixture in 8:2 ratios as eluent. The pure compound was crystallized in ethyl acetate and hexane to obtain light red blocks.

¹H NMR (DMSO-d6, 300 MHz): δ 7.33 (t, J=7.2 Hz, 2H), 7.13 (t, J=8.7 Hz, 4H), 7.02 (t, J=7.2 Hz, 2H), 6.75 (s, 2H), 4.51 (d, J=1.8 Hz, 2H), 3.08 (s, 1H).

MS (M⁺+1): 232. Melting point (°C): 90 (Uncorrected)