3-Hy­droxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

Mohamed Rida; Khalil Mamari; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536811054456

. 2011 Dec 23;68(Pt 1):o238. doi: 10.1107/S1600536811054456

3-Hydroxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Mohamed Rida ^a, Khalil Mamari ^a, El Mokhtar Essassi ^a, Seik Weng Ng ^b,^c,^*

PMCID: PMC3254569 PMID: 22259519

Abstract

The asymmetric unit of the title compound, C₁₈H₁₈N₂O₂, contains three independent molecules. In each, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern. In the crystal, the molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds. The allyl group of one molecule is equally disordered over two positions.

Related literature

For a related structure, see: Rida et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₁₈N₂O₂
M _r = 294.34
Monoclinic,
a = 51.6665 (8) Å
b = 14.5766 (2) Å
c = 11.9316 (2) Å
β = 90.965 (2)°
V = 8984.7 (2) Å³
Z = 24
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.21 × 0.15 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer
98635 measured reflections
11182 independent reflections
8815 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.153
S = 1.01
11182 reflections
604 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054456/xu5411sup1.cif

e-68-0o238-sup1.cif^{(37.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054456/xu5411Isup2.hkl

e-68-0o238-Isup2.hkl^{(546.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811054456/xu5411Isup3.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
O1—H1o⋯O2ⁱ	0.84	1.96	2.786 (2)	167
O5—H5o⋯O6ⁱⁱ	0.84	2.30	3.022 (2)	145
N1—H1n⋯O3	0.88	2.58	3.142 (2)	123
N3—H3n⋯O4ⁱⁱⁱ	0.88	2.40	2.900 (2)	116

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

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

A previous study describes 3-hydroxy-4-phenyl-1-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepine-2(3H)-one (Rida et al., 2011). The present study has an ally group in place of the 3-phenyl-4,5-dihyro-1,2-oxazol-5-yl group. The compound, C₁₈H₁₈N₂O₂ (Scheme I) crystallizes as three independent molecules, one of which has the allyl group disordered over two positions (Fig. 1). In these three molecules, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern.

Despite the present of amino and hydroxy groups, the crystal structure features few hydrogen bonds (Table 1).

Experimental

To a solution of 3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one (1 g, 3.5 mmol) in DMF (20 ml) were added allyl bromide (0.5 g. 4.2 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic quantity of tetra-n-buthyl ammonium bromide. The mixture was stirred at room temperature for 24 hours. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford the compound as colorless crystals.