3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione monohydrate

R Dardouri; Y Kandri Rodi; Natalie Saffon; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536810005325

. 2010 Feb 13;66(Pt 3):o633. doi: 10.1107/S1600536810005325

3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione monohydrate

R Dardouri ^a, Y Kandri Rodi ^a, Natalie Saffon ^b, El Mokhtar Essassi ^c, Seik Weng Ng ^d,^*

PMCID: PMC2983709 PMID: 21580389

Abstract

In the title compound, C₂₁H₂₁N₅O₂·H₂O, the seven-membered ring adopts a boat-shaped conformation with the methine C atom as the prow. In the crystal, the water molecule links adjacent molecules by O—H⋯O and O—H⋯N hydrogen bonds into a zigzag chain running along the c axis of the monoclinic cell.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 ▶). For the water-free structure of 1-benzyl-4-[(1,5-dimethyl-2,4-dioxobenzo-1,5-diazepin-3-yl)methyl]-1,2,3-triazole, see: Dardouri et al. (2010 ▶).

Experimental

Crystal data

C₂₁H₂₁N₅O₂·H₂O
M _r = 393.44
Monoclinic,
a = 9.6002 (1) Å
b = 11.9497 (2) Å
c = 17.0860 (2) Å
β = 92.527 (1)°
V = 1958.19 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII diffractometer
34134 measured reflections
4673 independent reflections
3454 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.108
S = 1.02
4673 reflections
272 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005325/bt5193sup1.cif

e-66-0o633-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005325/bt5193Isup2.hkl

e-66-0o633-Isup2.hkl^{(228.9KB, 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
O1W—H1⋯O2	0.85 (1)	2.02 (1)	2.836 (2)	161 (2)
O1W—H2⋯N3ⁱ	0.85 (1)	2.10 (1)	2.937 (2)	170 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Université Sidi Mohamed Ben Abdallah, the Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution of 1,5-dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione (8.26 × 10 ^-4 mol) in toluene (15 ml) was added benzyl azide (9.91 × 10 ^-4 mol). The mixture was stirred under reflux and the reaction was monitored by thin layer chromatography. On completion of the reaction, the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 2/1). Crystals were obtained when the solvent was allowed to evaporate.