4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one

Mehmet Akkurt; Alan R Kennedy; Sabry H H Younes; Shaaban K Mohamed; Antar A Abdelhamid

doi:10.1107/S160053681204651X

. 2012 Nov 17;68(Pt 12):o3356. doi: 10.1107/S160053681204651X

4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one

Mehmet Akkurt ^a,^*, Alan R Kennedy ^b,^*, Sabry H H Younes ^c, Shaaban K Mohamed ^d,^e, Antar A Abdelhamid ^d

PMCID: PMC3588955 PMID: 23476191

Abstract

In the title compound, C₁₅H₁₂N₂O, the phenyl ring makes a dihedral angle of 32.45 (9)° with the benzene ring of the 1,5-benzodiazepin-2-one unit. The seven-membered ring adopts a boat conformation with the methylene group as the prow and the fused benzene-ring C atoms as the stern. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops. The dimers are further linked by C—H⋯O hydrogen bonds, so forming a column along the a-axis direction.

Related literature

For background to benzodiazepine compounds, see: McKernan (2000 ▶); Thakur et al. (2003 ▶). For related structures, see: Benelbaghdadi et al. (2003 ▶); Višnjevac et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₂N₂O
M _r = 236.27
Triclinic,
a = 4.6894 (5) Å
b = 10.8353 (13) Å
c = 11.7540 (13) Å
α = 77.721 (10)°
β = 83.805 (9)°
γ = 82.112 (10)°
V = 576.13 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.35 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.928, T _max = 1.000
4335 measured reflections
2584 independent reflections
1830 reflections with I > 2σI
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.140
S = 1.02
2584 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

Click here for additional data file.^{(22.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204651X/hb6983sup1.cif

e-68-o3356-sup1.cif^{(22.9KB, cif)}

Click here for additional data file.^{(124.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204651X/hb6983Isup2.hkl

e-68-o3356-Isup2.hkl^{(124.3KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681204651X/hb6983Isup3.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
N1—H1N⋯O1ⁱ	0.91 (2)	1.99 (2)	2.900 (2)	175 (2)
C1—H1B⋯O1ⁱⁱ	0.99	2.56	3.468 (2)	153

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

Due to their wide range of pharmacological activity in synthetic and industrial applications, benzodiazepines (BZDs) have attracted the interest of chemists and biologists. They are widely used as anti-inflammatory, analgesic, hypnotic, tranquillizers and anti-depressive agents (e.g. Thakur et al. 2003; McKernan, 2000).

In the title molecule (I), (Fig. 1), the C10–C15 phenyl and C3–C8 benzene rings make a dihedral angle of 32.45 (9)° with each other. All bond lengths and bond angles in (I) are comparable to those reported for similar compounds (Višnjevac et al., 2002; Benelbaghdadi et al., 2003).

The seven-membered ring (N1/N2/C1—C3/C8/C9) of the 1,3-dihydro-2H-1,5-benzodiazepin-2-one moiety exhibits a puckered conformation, with puckering parameters q₂= 0.7977 (19) Å, φ₂ = 337.34 (14)°, q₃= 0.250 (2) Å, φ₃ = 228.2 (5)°, and Q_T= 0.836 (2) Å.

In the crystal, a pair of N—H···O hydrogen bonds (Table 1) link two molecules into an inversion dimer with an R₂²(8) motif. Furhermore, C—H···O hydrogen bonds link the dimers, so forming a column along the a axis direction (Fig. 2).

Experimental

To a stirred boiling solution of 0.1 mol (10.8 g) benzene-1,2-diamine in 100 ml p-xylene, 0.12 mol (23.12 g) ethyl 3-oxo-3-phenylpropanoate was added in dropwise and refluxed for 2 h. The reaction mixture was left to stand at room temperature for 24 h. The precipitated solid was collected by filtration and recrystallized from benzene to give colourless rods in 90% yield (M.p. 480 K).