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

Fadare, O.A.; Adelani, P.O.; Ikotun, A.A.; Obafemi, C.A.

doi:10.1107/S1600536812016194

Volume 68
Part 5
Pages o1508-o1509
May 2012

Received 18 March 2012
Accepted 13 April 2012
Online 25 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.106
Data-to-parameter ratio = 17.6
Details

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 and Craig A. Obafemi ^a ^*

^aChemistry Department, Obafemi Awolowo University, Ile-ife, Nigeria,^bDepartment of Civil Engineering and Geological Sciences, and Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA, and ^cChemistry and Industrial Chemistry Department, Bowen University, Iwo, Nigeria
Correspondence e-mail: adeyemi01@yahoo.com

In the title compound, C₂₂H₂₄N₂O₂·H₂O, the co-crystallized water molecule interacts with the N and O atoms of the molecule through O_w-HN, O_w-HO(methyl) and N-HO_w hydrogen-bonding interactions. These hydrogen bonds, along with the intermolecular N-HO=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, P 2₁ /c
a = 10.684 (7) Å
b = 16.973 (12) Å
c = 11.174 (8) Å
= 101.490 (9)°
V = 1986 (2) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.106
S = 0.83
4529 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1Wⁱ	0.86	2.14	2.994 (3)	170
O1W-H1BN2ⁱⁱ	0.98 (3)	2.04 (3)	3.020 (3)	178.2 (14)
O1W-H1CO2	0.99 (2)	1.85 (2)	2.832 (3)	170 (2)
N2-H2CO1ⁱⁱⁱ	0.949 (18)	2.099 (18)	3.047 (3)	177.4 (13)
Symmetry codes: (i) -x+2, -y, -z; (ii) x+1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: FF2060 ).

Acknowledgements

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

References

Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.
Beccalli, E. M., Broggini, G., Paladino, G. & Zoni, C. (2005). Tetrahedron, 61, 61-68.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cortés, C. E., Cornejo, A. L. V. & García, M. O. (2007). J. Heterocycl. Chem. 44, 183-187.
Farnet, C. M., Dimitriadou, V. & Bachmann, B. O. (2005). US Patent Appl. 107363 A1.
Hanze, A. R., Strube, R. E. & Greig, M. E. (1963). J. Med. Chem. 6, 767-771.
Joergensen, T. K., Andersen, K. E., Andersen, H. S., Hohlweg, R., Madsen, P. & Olsen, U. B. (1996). PCT Int. Appl. WO9631497 A1.
Kolos, N. N., Yurchenko, E. N., Orlov, V. D., Shishkina, S. V. & Shishkin, O. V. (2004). Chem. Heterocycl. Compd, 40, 1550-1559.
McAlpine, J. B., Banskota, A. H. & Aouidate, M. (2008). US Patent Appl. 161291 A1.
McGowan, D., et al. (2009). Bioorg. Med. Chem. Lett. 19, 2492-2496.
Rashed, N., Sayed, M. & El-Ashry, E. S. H. (1993). J. Chin. Chem. Soc. 40, 189-194.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds