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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 [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.106
Data-to-parameter ratio = 17.6
Details
Open access

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

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 Ow-H...N, Ow-H...O(methyl) and N-H...Ow 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[Hanze, A. R., Strube, R. E. & Greig, M. E. (1963). J. Med. Chem. 6, 767-771.]); Rashed et al. (1993[Rashed, N., Sayed, M. & El-Ashry, E. S. H. (1993). J. Chin. Chem. Soc. 40, 189-194.]); Kolos et al. (2004[Kolos, N. N., Yurchenko, E. N., Orlov, V. D., Shishkina, S. V. & Shishkin, O. V. (2004). Chem. Heterocycl. Compd, 40, 1550-1559.]); Cortés et al. (2007[Cortés, C. E., Cornejo, A. L. V. & García, M. O. (2007). J. Heterocycl. Chem. 44, 183-187.]); Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]). For the biological activity of dibenzo[b,e][1,4]diazepinones, see: Beccalli et al. (2005[Beccalli, E. M., Broggini, G., Paladino, G. & Zoni, C. (2005). Tetrahedron, 61, 61-68.]); Farnet et al. (2005[Farnet, C. M., Dimitriadou, V. & Bachmann, B. O. (2005). US Patent Appl. 107363 A1.]); Joergensen et al. (1996[Joergensen, T. K., Andersen, K. E., Andersen, H. S., Hohlweg, R., Madsen, P. & Olsen, U. B. (1996). PCT Int. Appl. WO9631497 A1.]); McAlpine et al. (2008[McAlpine, J. B., Banskota, A. H. & Aouidate, M. (2008). US Patent Appl. 161291 A1.]); McGowan et al. (2009[McGowan, D., et al. (2009). Bioorg. Med. Chem. Lett. 19, 2492-2496.]).

[Scheme 1]

Experimental

Crystal data
  • C22H24N2O2·H2O

  • Mr = 366.45

  • Monoclinic, P 21 /c

  • a = 10.684 (7) Å

  • b = 16.973 (12) Å

  • c = 11.174 (8) Å

  • [beta] = 101.490 (9)°

  • V = 1986 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.244, Tmax = 0.323

  • 22692 measured reflections

  • 4529 independent reflections

  • 2187 reflections with I > 2[sigma](I)

  • Rint = 0.087

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

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)
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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
Beccalli, E. M., Broggini, G., Paladino, G. & Zoni, C. (2005). Tetrahedron, 61, 61-68.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort] [ISI]
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.  [CrossRef] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
Rashed, N., Sayed, M. & El-Ashry, E. S. H. (1993). J. Chin. Chem. Soc. 40, 189-194.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o1508-o1509   [ doi:10.1107/S1600536812016194 ]

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