1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rachid Dardouri; F Ouazzani Chahdi; Natalie Saffon; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536810024219

. 2010 Jun 26;66(Pt 7):o1797. doi: 10.1107/S1600536810024219

1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rachid Dardouri ^a, F Ouazzani Chahdi ^a, Natalie Saffon ^b, El Mokhtar Essassi ^c, Seik Weng Ng ^d,^*

PMCID: PMC3006968 PMID: 21588007

Abstract

The asymmetric unit of the title compound, C₁₄H₁₄N₂O₂, comprises two independent molecules, which slightly differ in the orientation of the propargyl chain. In both molecules, the diazepine ring adopts a boat conformation with the propargyl-bearing C atom as the prow and the C atoms at the ring junction as the stern. The carbonyl O atom of one independent molecule is hydrogen bonded to the acetylenic H atom of the other independent molecule. In the crystal, symmetry-related molecules are linked together by C—H⋯O hydrogen bonds, forming a ribbon-like structure along the c axis.

Related literature

For a related structure, see: Jabli et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M _r = 242.27
Monoclinic,
a = 16.0768 (3) Å
b = 17.1087 (3) Å
c = 8.9530 (2) Å
β = 93.701 (1)°
V = 2457.42 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.05 mm

Data collection

Bruker X8 APEXII area-detector diffractometer
21953 measured reflections
3580 independent reflections
2637 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.105
S = 1.06
3580 reflections
337 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536810024219/ci5110sup1.cif

e-66-o1797-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024219/ci5110Isup2.hkl

e-66-o1797-Isup2.hkl^{(175.6KB, 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
C13—H13⋯O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8⋯O2ⁱ	0.98	2.56	3.536 (3)	175
C19—H19⋯O1ⁱ	0.93	2.49	3.374 (3)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

We recently reported the crystal stucture of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, a compound readily synthesized by reacting the disubstituted 1,5-benzodiazepine-2,4-dione with propargyl bromide (Jabli et al., 2009). The background to the study of such compounds is given in other reports. Replacing the benzyl unit by a methyl unit in the present study gives a compoound having a diazepine ring system (Scheme I, Fig. 1). This ring adopts a boat conformation (with the propargyl-bearing C atom as the prow and the fused-ring C atoms as the stern). There are two independent molecules; the acetylenic H-atom of one molecule forms a hydrogen to the carbonyl O-atom of the other independent molecule.

Experimental

To a solution of potassium t-butoxide (0.42 g, 3.6 mmol) in DMF (15 ml) was added 1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.50 g, 2.4 mmol) and propargyl bromide (0.26 ml, 2.87 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer chromatography. On completion of the reaction, the mixture was filtered; crystals were obtained when the solvent was allowed to evaporate.