11-(4-Meth­oxy­phen­yl)-3,3-dimethyl-2,3,4,5,10,11-hexa­hydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

Olatomide A Fadare; Pius O Adelani; Adebomi A Ikotun; Craig A Obafemi

doi:10.1107/S1600536812016194

. 2012 Apr 25;68(Pt 5):o1508–o1509. doi: 10.1107/S1600536812016194

11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

Olatomide A Fadare ^a, Pius O Adelani ^b, Adebomi A Ikotun ^c, Craig A Obafemi ^a,^*

PMCID: PMC3344616 PMID: 22590378

Abstract

In the title compound, C₂₂H₂₄N₂O₂·H₂O, the co-crystallized water molecule interacts with the N and O atoms of the molecule through O_w—H⋯N, O_w—H⋯O(methyl) and N—H⋯O_w hydrogen-bonding interactions. These hydrogen bonds, along with the intermolecular N—H⋯O=C hydrogen-bonding interactions, connect the molecules into a three-dimensional network. The dihedral angle between the two aromatic rings is 65.46 (10)°.

Related literature

For details of the synthesis, see: Hanze et al. (1963 ▶); Rashed et al. (1993 ▶); Kolos et al. (2004 ▶); Cortés et al. (2007 ▶); Ajani et al. (2010 ▶). For the biological activity of dibenzo[b,e][1,4]diazepinones, see: Beccalli et al. (2005 ▶); Farnet et al. (2005 ▶); Joergensen et al. (1996 ▶); McAlpine et al. (2008 ▶); McGowan et al. (2009 ▶).

Experimental

Crystal data

C₂₂H₂₄N₂O₂·H₂O
M _r = 366.45
Monoclinic,
a = 10.684 (7) Å
b = 16.973 (12) Å
c = 11.174 (8) Å
β = 101.490 (9)°
V = 1986 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.04 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.244, T _max = 0.323
22692 measured reflections
4529 independent reflections
2187 reflections with I > 2σ(I)
R _int = 0.087

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.106
S = 0.83
4529 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016194/ff2060sup1.cif

e-68-o1508-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016194/ff2060Isup2.hkl

e-68-o1508-Isup2.hkl^{(221.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016194/ff2060Isup3.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—H1A⋯O1Wⁱ	0.86	2.14	2.994 (3)	170
O1W—H1B⋯N2ⁱⁱ	0.98 (3)	2.04 (3)	3.020 (3)	178.2 (14)
O1W—H1C⋯O2	0.99 (2)	1.85 (2)	2.832 (3)	170 (2)
N2—H2C⋯O1ⁱⁱⁱ	0.949 (18)	2.099 (18)	3.047 (3)	177.4 (13)

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

Acknowledgments

We thank the Central Science Laboratory, Obafemi Awolowo University, Ile-ife, for supporting this study.

supplementary crystallographic information

Comment

Dibenzo[b,e][1,4]diazepinones are useful intermediates in the synthesis of pharmaceuticals. For example, dibenzo[b,e][1,4]diazepin-11-ones are useful intermediates in the preparation of dibenzo[1,4]diazepines (Hanze et al., 1963). They display wide variety of biological properties, including antidepressant (Beccalli et al., 2005), antimicrobial (Farnet et al., 2005), analgesic and anti-inflammatory (Joergensen et al., 1996), antitumor (McAlpine et al., 2008) activities, while the dibenzodiazepin-1-ones are hepatitis C virus (HCV) NS5B polymerase inhibitors (McGowan et al., 2009). In view of our interest in bioactivity of nitrogen-containing heterocyclic compounds (see: Ajani et al., 2010), we report here the microwave-assisted synthesis and the crystal structure of the title compound 1.

Experimental

A mixture of dimedone (2.0 g, 14.3 mmol) and o-phenylenediamine (1.54 g, 14.3 mmol) in absolute ethanol (30 ml), containing acetic acid (0.5 ml), in a beaker was pulse irradiated in a microwave oven for 5 min. and left to stand at room temperature for 1 h. Anisaldehyde (1.95 g, 14.3 mmol) was added to the reaction mixture and then subjected to microwave irradiation for 5 min. (TLC monitored). Evaporation of the solvent afforded a gummy product. Cold aqueous ethanol was added with scratching to give yellow precipitate (melting point 202–205 ^o C). Crystals of 1 suitable for X-ray analysis were obtained by slow evaporation of ethanol solution of the product.