(E)-2-(5,5-Dimethyl­hexa­hydro­pyrimidin-2-yl)-4-(phenyl­diazen­yl)phenol

Sheikhshoaie, I.; Monadi, N.; Abbasi, A.

doi:10.1107/S1600536808038877

Volume 64
Part 12
Page o2453
December 2008

Received 18 November 2008
Accepted 19 November 2008
Online 26 November 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.114
Data-to-parameter ratio = 13.4
Details

(E)-2-(5,5-Dimethylhexahydropyrimidin-2-yl)-4-(phenyldiazenyl)phenol

Iran Sheikhshoaie,^a Niaz Monadi ^a and Alireza Abbasi ^b ^*

^aChemistry Department, Shahid Bahonar University, Kerman, Iran, and ^bSchool of Chemistry, University College of Science, University of Tehran, Tehran, Iran
Correspondence e-mail: aabbasi@khayam.ut.ac.ir

In the title Schiff base, C₁₈H₂₂N₄O, the hexahydropyrimidinyl ring adopts a chair conformation. The dihedral angle between the aromatic rings of the 4-(2-phenyldiazenyl)phenol unit is 15.7 (1)°. There is an intramolecular O-HN hydrogen bond between the hydroxyl group and an N atom of the hexahydropyimidinyl unit. Intermolecular N-HO and N-HN hydrogen bonds give rise to a layer structure.

Related literature

For applications and related structures, see: Farrell et al. (2007).

Experimental

Crystal data

C₁₈H₂₂N₄O
M_r = 310.40
Orthorhombic, P b c a
a = 9.0287 (9) Å
b = 12.0767 (12) Å
c = 30.866 (3) Å
V = 3365.5 (6) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 120 (2) K
0.23 × 0.20 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.970, T_max = 0.987
14483 measured reflections
3134 independent reflections
1574 reflections with I > 2(I)
R_int = 0.078

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.114
S = 0.81
3134 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN3	1.01 (2)	1.65 (2)	2.584 (2)	152 (2)
N3-H3AN4ⁱ	0.92 (2)	2.30 (2)	3.159 (3)	155 (2)
N4-H4AO1ⁱⁱ	0.93 (2)	2.18 (2)	3.106 (3)	172 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2518 ).

Acknowledgements

This work was supported by a grant from the University of Kerman and the University of Tehran.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrell, J. R., Niconchuk, J., Higham, C. S. & Bergeron, B. W. (2007). Tetrahedron Lett. 48, 8034-8036.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds