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Volume 68 
Part 11 
Page o3085  
November 2012  

Received 20 September 2012
Accepted 1 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 23.5
Details
Open access

3-[Bis(dimethylamino)methylene]-1,1-diphenylurea

aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
Correspondence e-mail: Ioannis.Tiritiris@htw-aalen.de

In the title compound, C18H22N4O, the C=N and C-N bond lengths in the CN3 unit are 1.3179 (11), 1.3551 (11) and 1.3737 (11) Å, indicating double- and single-bond character, respectively. The N-C-N angles are 115.91 (8), 118.20 (8) and 125.69 (8), showing a deviation of the CN3 plane from an ideal trigonal-planar geometry. The bonds between the N atoms and the terminal C-methyl groups all have values close to a typical single bond [1.4529 (12)-1.4624 (12) Å]. The dihedral angle between the phenyl rings is 79.63 (4)°. In the crystal, the molecules are connected via weak C-H...O hydrogen bonds, generating chains along [100].

Related literature

For synthesis of N-dimethylcarbamoyl-N',N',N'',N''-tetramethylguanidine, see: Möllers et al. (2003[Möllers, C., Prigge, J., Wibbeling, B., Fröhlich, R., Brockmeyer, A., Schäfer, H. J., Schmälzlin, E., Bräuchle, C., Meerholz, K. & Würthwein, E.-U. (2003). Eur. J. Org. Chem. 1198-1208.]). For the crystal structures of 2- and 5-azido-N-(diphenylcarbamoyl) proline methyl ester, see: Lynch et al. (1995[Lynch, V. M., Hulme, C., Magnus, P. & Davis, B. E. (1995). Acta Cryst. C51, 2598-2601.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N4O

  • Mr = 310.40

  • Monoclinic, P 21 /c

  • a = 7.9321 (3) Å

  • b = 17.0477 (9) Å

  • c = 12.2151 (6) Å

  • [beta] = 98.583 (2)°

  • V = 1633.28 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker Kappa APEXII Duo diffractometer

  • 51490 measured reflections

  • 4990 independent reflections

  • 4200 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.105

  • S = 1.04

  • 4990 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11A...O1i 0.95 2.59 3.3893 (12) 141
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, D-53002 Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2403 ).


Acknowledgements

The author thanks Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for the data collection.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, D-53002 Bonn, Germany.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Lynch, V. M., Hulme, C., Magnus, P. & Davis, B. E. (1995). Acta Cryst. C51, 2598-2601.  [CrossRef] [details]
Möllers, C., Prigge, J., Wibbeling, B., Fröhlich, R., Brockmeyer, A., Schäfer, H. J., Schmälzlin, E., Bräuchle, C., Meerholz, K. & Würthwein, E.-U. (2003). Eur. J. Org. Chem. 1198-1208.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3085  [ doi:10.1107/S160053681204127X ]

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