5-[(3,5-Dichloro­anilino)meth­yl]-N-(3,5-dichloro­phen­yl)-6-methyl-2-phenyl­pyrimidin-4-amine

Cieplik, J.; Pluta, J.; Bryndal, I.; Lis, T.

doi:10.1107/S160053681204665X

Volume 68
Part 12
Page o3412
December 2012

Received 7 November 2012
Accepted 12 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 85 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.100
Data-to-parameter ratio = 27.2
Details

5-[(3,5-Dichloroanilino)methyl]-N-(3,5-dichlorophenyl)-6-methyl-2-phenylpyrimidin-4-amine

Jerzy Cieplik,^a Janusz Pluta,^b Iwona Bryndal ^c ^* and Tadeusz Lis ^d

^aDepartment of Organic Chemistry, Wroclaw Medical University, 9 Grodzka St, 50-137 Wroclaw, Poland,^bDepartment of Applied Pharmacy, Wroclaw Medical Uniwersity, 38 Szewska St, 50-137 Wroclaw, Poland,^cDepartment of Bioorganic Chemistry, Faculty of Engineering and Economics, Wroclaw University of Economics, 118/120 Komandorska St, 53-345 Wroclaw, Poland, and ^dFaculty of Chemistry, University of Wroclaw, 14 Joliot-Curie St, 50-383 Wroclaw, Poland
Correspondence e-mail: isai@o2.pl

In the title compound, C₂₄H₁₈Cl₄N₄, the pyrimidine ring makes dihedral angles of 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively, with phenyl and two benzene rings, and the molecular conformation is stabilized by an intramolecular N-HN hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of intermolecular N-HN hydrogen bonds connect two molecules, forming inversion dimers with R₂²(12) motifs. C-H [pi] interactions links the dimers into a chain running along the a-axis direction. There are also [pi] - [pi] stacking interactions [centroid-centroid distance = 3.666 (4) Å] between the benzene rings of adjacent chains.

Related literature

For the antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (2003, 2008). For related structures, see: Cieplik et al. (2006, 2012).

Experimental

Crystal data

C₂₄H₁₈Cl₄N₄
M_r = 504.22
Triclinic, $[P \overline 1]$
a = 8.267 (3) Å
b = 11.271 (4) Å
c = 12.788 (4) Å
= 76.53 (5)°
= 78.95 (5)°
= 81.42 (5)°
V = 1130.4 (7) Å³
Z = 2
Mo K radiation
= 0.54 mm^-1
T = 85 K
0.23 × 0.14 × 0.08 mm

Data collection

Oxford Xcalibur PX with Onyx CCD diffractometer
19215 measured reflections
8041 independent reflections
5082 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.100
S = 1.03
8041 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.75 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21-C26 ring.

D-HA	D-H	HA	DA	D-HA
N4-H4N5	0.85 (2)	2.19 (2)	2.875 (3)	137.6 (17)
N5-H5N1ⁱ	0.81 (2)	2.40 (2)	3.171 (3)	158.1 (19)
C57-H572Cg1ⁱⁱ	0.99	2.65	3.62 (2)	166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5217 ).

References

Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259-o261.
Cieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146-150.
Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427-434.
Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729-o1730.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds