6-Chloro-N 2,N 4-di-p-tolyl-1,3,5-triazine-2,4-diamine dimethyl­formamide monosolvate

Fangfang Jian; Hailian Xiao; Yongxiang Wei

doi:10.1107/S1600536809049885

. 2009 Nov 25;65(Pt 12):o3212. doi: 10.1107/S1600536809049885

6-Chloro-N ²,N ⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine dimethylformamide monosolvate

Fangfang Jian ^a,^*, Hailian Xiao ^b, Yongxiang Wei ^b

PMCID: PMC2972005 PMID: 21578920

Abstract

The title compound, C₁₇H₁₆ClN₅·C₃H₇NO, was prepared by reaction of p-toluidine with 2,4,6-trichloro-1,3,5-triazine at room temperature. The dihedral angles between the triazine ring and the pendant rings are 3.61 (12) and 53.11 (12)°. An intramolecular C—H⋯N interaction occurs. The packing is stabilized by N—H⋯N and N—H⋯O hydrogen bonds and C—H⋯π and π–π [centroid–centroid distance = 3.763 (1) Å] interactions.

Related literature

For the use of 1,3,5-triazine derivatives as starting materials for drugs and as light stabilisers, see: Azev et al. (2003 ▶); Steffensen and Simanek (2003 ▶). For related structures, see: Zeng et al. (2005a ▶,b ▶); Jian et al. (2007 ▶). graphic file with name e-65-o3212-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₆ClN₅·C₃H₇NO
M _r = 398.89
Triclinic,
a = 6.821 (2) Å
b = 10.980 (2) Å
c = 14.060 (3) Å
α = 91.13 (3)°
β = 94.29 (2)°
γ = 98.32 (4)°
V = 1038.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
5740 measured reflections
3832 independent reflections
2786 reflections with I > 2σ(I)
R _int = 0.016
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.146
S = 1.02
3832 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049885/hg2590sup1.cif

e-65-o3212-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049885/hg2590Isup2.hkl

e-65-o3212-Isup2.hkl^{(187.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.06	2.923 (3)	177
N2—H2A⋯N5ⁱ	0.86	2.24	3.081 (3)	168
C4—H4A⋯N3	0.93	2.30	2.905 (3)	122
C1—H1D⋯Cg1ⁱⁱ	0.96	2.86	3.653 (4)	145

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C2–C7 ring.

Acknowledgments

The authors would like to thank the Natural Science Foundation of Shandong Province (Nos. Y2006B08 and Z2007B01).

supplementary crystallographic information

Comment

1,3,5-Triazine derivatives are of great interest due to their importance as starting materials for drugs and light stabilizers (Azev et al., 2003; Steffensen & Simanek, 2003; Zeng et al., 2005a). Our group has reported the structure of 1,3,5-triazine derivative (Jian et al., 2007). Herein, we report the synthesis and structure of the title compound.

The crystal structure consists of the host 1,3,5-triazine derivative and a guest DMF solvate molecule. The bond lengths and angles are agreement with those found in similar compounds (Zeng et al., 2005b; Jian et al., 2007). The dihedral angles formed by triazine ring and two phenyl ring are 3.61, 53.11° for C2—C7 and C9—C14, respectively. They are compared to those found in the compound that reported by our group before (Jian et al., 2007). The dihedral angle between two phenyl ring is 51.61 (2)° which is larger than that of 35.8 (1)° found in aforementioned compound.

It is interesting that there exists C—H···π and π–π interactions in the lattice [C1···Cg1=3.653 (4) Å, C1—H1D···Cg1=145.1 (1)°, Cg1···Cg2=3.763 (1) Å,Cg1 and Cg2 refer to phenyl ring C2—C7 and triazine ring, respectively]. In addition there exists N—H···O, N—H···N, C—H···N and C—H···O intra and intermolecular hydrogen bond interactions (see Table 1). All the above interactions stabilize the whole structure.

Experimental

The title compound was synthesized by the reaction of 2,4,6-trichloro-1,3,5-triazine (0.02 mol) and p-toluidine (0.04 mol) in acetone solvate (50 ml) under stirring for 5 h at room temperature. Single crystals suitable for x-ray measurements were obtained by recrystallization from DMF at room temperature.