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Volume 70 
Part 1 
Page o32  
January 2014  

Received 5 November 2013
Accepted 4 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.099
Data-to-parameter ratio = 14.1
Details
Open access

(E)-3-[(Di­methyl­amino)­methyl­idene]-4-phenyl-1-(prop-2-yn­yl)-1H-1,5-benzodiazepin-2(3H)-one

aLaboratoire de Chimie Moléculaire, Département de Chimie, Faculté des Sciences-Semlalia, BP 2390, Université Cadi Ayyad, 40001 Marrakech, Morocco,bDepartment of Chemistry, University of Aveiro, CICECO, 3810-193 Aveiro, Portugal,cDepartment of Chemistry, University of Aveiro, QOPNA, 3810-193 Aveiro, Portugal, and dEquipe de Chimie des Matériaux et de l'Environnement, FSTG-Marrakech, Université Cadi Ayyad, Bd Abdelkrim Khattabi, BP 549, Marrakech, Morocco
Correspondence e-mail: eh_soumhi@yahoo.fr

The title compound, C21H19N3O, exhibits an E configuration with respect to the C=C bond between the benzodiazepine and tri­methyl­amine groups. The seven-membered diazepine ring displays a boat conformation. In the crystal, mol­ecules are linked by a C-H...O hydrogen bond, forming a chain along [110].

Related literature

For benzodiazepine derivatives, see: Di Braccio et al. (2001[Di Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). Eur. J. Med. Chem. 36, 935-949.]); Pevarello et al. (1993[Pevarello, P., Amici, R., Colombo, M. & Varasi, M. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 2151-2152.]). For related structures, see: Loughzail et al. (2011[Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075-o2076.]); Boudina et al. (2006[Boudina, A., Baouid, A., Hasnaoui, A. & Essaber, M. (2006). Synth. Commun. 36, 573-579.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19N3O

  • Mr = 329.39

  • Monoclinic, C 2/c

  • a = 12.8122 (10) Å

  • b = 13.9317 (12) Å

  • c = 19.7795 (14) Å

  • [beta] = 94.647 (3)°

  • V = 3519.0 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.13 × 0.10 × 0.08 mm

Data collection
  • Bruker X8 KappaCCD APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.990, Tmax = 0.994

  • 21544 measured reflections

  • 3220 independent reflections

  • 2555 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.099

  • S = 1.02

  • 3220 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...O1i 0.93 2.50 3.415 (2) 170
Symmetry code: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5319 ).


References

Boudina, A., Baouid, A., Hasnaoui, A. & Essaber, M. (2006). Synth. Commun. 36, 573-579.  [Web of Science] [CrossRef] [ChemPort]
Bruker (2005). SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Di Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). Eur. J. Med. Chem. 36, 935-949.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075-o2076.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Pevarello, P., Amici, R., Colombo, M. & Varasi, M. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 2151-2152.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o32  [ doi:10.1107/S1600536813032960 ]

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