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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 [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.100
Data-to-parameter ratio = 27.2
Details
Open access

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

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-H...N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of intermolecular N-H...N 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[Cieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146-150.], 2008[Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427-434.]). For related structures, see: Cieplik et al. (2006[Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259-o261.], 2012[Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729-o1730.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18Cl4N4

  • Mr = 504.22

  • Triclinic, [P \overline 1]

  • a = 8.267 (3) Å

  • b = 11.271 (4) Å

  • c = 12.788 (4) Å

  • [alpha] = 76.53 (5)°

  • [beta] = 78.95 (5)°

  • [gamma] = 81.42 (5)°

  • V = 1130.4 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.75 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21-C26 ring.

D-H...A D-H H...A D...A D-H...A
N4-H4...N5 0.85 (2) 2.19 (2) 2.875 (3) 137.6 (17)
N5-H5...N1i 0.81 (2) 2.40 (2) 3.171 (3) 158.1 (19)
C57-H572...Cg1ii 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[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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CSD] [CrossRef] [details]
Cieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146-150.  [PubMed] [ChemPort]
Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427-434.  [ChemPort]
Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729-o1730.  [CSD] [CrossRef] [details]
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3412  [ doi:10.1107/S160053681204665X ]

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