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

Tiritiris, I.

doi:10.1107/S160053681204127X

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 (C-C) = 0.001 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 23.5
Details

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

Ioannis Tiritiris ^a ^*

^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-HO hydrogen bonds, generating chains along [100].

Related literature

For synthesis of N-dimethylcarbamoyl-N',N',N'',N''-tetramethylguanidine, see: Möllers et al. (2003). For the crystal structures of 2- and 5-azido-N-(diphenylcarbamoyl) proline methyl ester, see: Lynch et al. (1995).

Experimental

Crystal data

C₁₈H₂₂N₄O
M_r = 310.40
Monoclinic, P 2₁ /c
a = 7.9321 (3) Å
b = 17.0477 (9) Å
c = 12.2151 (6) Å
= 98.583 (2)°
V = 1633.28 (13) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.105
S = 1.04
4990 reflections
212 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11AO1ⁱ	0.95	2.59	3.3893 (12)	141
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); 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.
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.

organic compounds