6-Chloro-N2,N4-di-p-tolyl-1,3,5-triazine-2,4-diamine acetone solvate

Jian, F.-F.; Wei, Y.-X.; Huang, L.-H.; Ren, X.-Y.

doi:10.1107/S1600536807060151

6-Chloro-N²,N⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine acetone solvate

F.-F. Jian, Y.-X. Wei, L.-H. Huang and X.-Y. Ren

The title compound, C₁₈H₁₆ClN₅·C₂H₆O, was prepared by the reaction of p-toluidine with 2,4,6-trichloro-1,3,5-triazine at room temperature. The three rings are not coplanar; the dihedral angles between the triazine ring and the phenyl rings are 41.32 and 6.58°, and that between the two phenyl rings is 35.58°. The molecular structure and packing are stabilized by N—H

N, C—H

O and C—H

N hydrogen-bond interactions and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060151/at2472sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060151/at2472Isup2.hkl Contains datablock I

CCDC reference: 673107

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.009 Å
R factor = 0.077
wR factor = 0.329
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.329
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.33
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H16 Cl N5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H6 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The amine derivatives of 2,4,6-trichloro[1,3,5]triazine possess valuable properties, as they are widely used as starting materials for many products, including drugs and light stabilizers (Mathias & Simanek, 1994; Manasek & Hrdlovik, 1990). The title compound has been synthesized and we report here its crystal structure.

In the crystal structure (Fig. 1), it contains a solution molecule of acetone, and there is an interaction between the major molecule and the solution molecule. The bond lengths and angles of the major molecule (Table 1) is agreement with those of the similar compound 2,4-dichloro-6-aniline-1,3,5-triazine (Zeng, Dong & Shu, 2005; Zeng, Dong, Shu, Li & Huang, 2005). The atom N1 lies in the plan of phenyl C1—C7(p1). The atom N5 lies in the plan of phenyl C11—C17(p2). The dihedral angles formed by the triazine ring with p1 and p2 are 40.9 (8) and 6.3 (1)°, respectively. The dihedral angles between the plane p1 and p2 is 35.8 (1)°.

It exists two kind of C—H···Π interaction [C1···C_g1 = 3.806 (2), C17···C_g2 = 3.745 (2) Å and C1—H1···C_g1 = 141.1 (1), C17—H17C···C_g2 = 145.2 (2)°] (C_g1 = phenyl ring C2–C7, C_g2 = phenyl ring C11—C16). In addtion, there exist N—H···N and C—H···O intermolecular interactions (Table 1). All above interactions stabilize the title structure.

Related literature top

For related literature, see: Manasek & Hrdlovik (1990); Mathias & Simanek (1994); Zeng, Dong & Shu (2005); Zeng, Dong, Shu et al. (2005).

Experimental top

A mixture of 2,4,6-trichloro-1,3,5-triazine (0.02 mol) and p-toluidine (0.04 mol) was stirred with acetone (50 ml) at 293 K for 5 h, affording the title compound (4.8 g, yield 90%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature.

Computing details top

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

6-Chloro-N²,N⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine acetone solvate top

Crystal data top

C₁₈H₁₆ClN₅·C₂H₆O	F(000) = 808
M_r = 383.88	D_x = 1.234 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 221.3 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.8610 (16) Å	Cell parameters from 25 reflections
b = 22.579 (5) Å	θ = 4–14°
c = 12.012 (2) Å	µ = 0.20 mm⁻¹
β = 104.22 (3)°	T = 295 K
V = 2066.7 (7) Å³	Block, white
Z = 4	0.30 × 0.20 × 0.18 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.052
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.8°
Graphite monochromator	h = 0→9
ω scans	k = 0→26
4122 measured reflections	l = −14→14
3833 independent reflections	3 standard reflections every 100 reflections
1855 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.329	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1873P)² + 0.955P] where P = (F_o² + 2F_c²)/3
3833 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₈H₁₆ClN₅·C₂H₆O	V = 2066.7 (7) Å³
M_r = 383.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8610 (16) Å	µ = 0.20 mm⁻¹
b = 22.579 (5) Å	T = 295 K
c = 12.012 (2) Å	0.30 × 0.20 × 0.18 mm
β = 104.22 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.052
4122 measured reflections	3 standard reflections every 100 reflections
3833 independent reflections	intensity decay: none
1855 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.329	H-atom parameters constrained
S = 1.06	Δρ_max = 0.39 e Å⁻³
3833 reflections	Δρ_min = −0.48 e Å⁻³
244 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.1703 (2)	0.34124 (6)	0.34531 (14)	0.0828 (6)
N1	−0.0587 (6)	0.17534 (18)	0.0908 (4)	0.0636 (12)
H1A	−0.0266	0.1972	0.0411	0.076*
N2	0.0415 (6)	0.25289 (17)	0.2107 (4)	0.0618 (11)
N3	0.0340 (6)	0.24672 (17)	0.4102 (3)	0.0555 (11)
N4	−0.0697 (5)	0.16526 (16)	0.2826 (3)	0.0539 (10)
N5	−0.0776 (6)	0.16432 (17)	0.4782 (4)	0.0596 (11)
H5A	−0.0589	0.1850	0.5401	0.071*
C1	−0.3658 (9)	−0.0448 (3)	−0.0980 (6)	0.0835 (18)
H1B	−0.4447	−0.0375	−0.1714	0.125*
H1C	−0.4286	−0.0630	−0.0479	0.125*
H1D	−0.2735	−0.0707	−0.1074	0.125*
C2	−0.2877 (7)	0.0130 (2)	−0.0466 (5)	0.0627 (13)
C3	−0.3263 (8)	0.0658 (3)	−0.1043 (5)	0.0755 (17)
H3B	−0.4030	0.0658	−0.1769	0.091*
C4	−0.2545 (8)	0.1189 (2)	−0.0577 (5)	0.0718 (16)
H4B	−0.2851	0.1540	−0.0983	0.086*
C5	−0.1370 (7)	0.1200 (2)	0.0493 (5)	0.0589 (13)
C6	−0.0954 (7)	0.0678 (2)	0.1096 (5)	0.0611 (14)
H6A	−0.0180	0.0679	0.1819	0.073*
C7	−0.1702 (7)	0.0153 (2)	0.0614 (5)	0.0669 (15)
H7A	−0.1410	−0.0197	0.1025	0.080*
C8	−0.0285 (6)	0.1978 (2)	0.1980 (4)	0.0519 (12)
C9	0.0696 (7)	0.2725 (2)	0.3187 (5)	0.0573 (13)
C10	−0.0386 (6)	0.19227 (19)	0.3868 (4)	0.0495 (11)
C11	−0.1436 (6)	0.1068 (2)	0.4875 (4)	0.0546 (12)
C12	−0.1980 (8)	0.0673 (2)	0.3971 (5)	0.0697 (15)
H12A	−0.1983	0.0788	0.3227	0.084*
C13	−0.2515 (8)	0.0108 (2)	0.4176 (5)	0.0751 (16)
H13A	−0.2861	−0.0151	0.3561	0.090*
C14	−0.2555 (7)	−0.0086 (2)	0.5272 (6)	0.0678 (15)
C15	−0.2045 (8)	0.0315 (3)	0.6166 (6)	0.0783 (17)
H15A	−0.2064	0.0201	0.6907	0.094*
C16	−0.1509 (8)	0.0881 (3)	0.5978 (5)	0.0733 (16)
H16A	−0.1191	0.1142	0.6592	0.088*
C17	−0.3135 (8)	−0.0711 (2)	0.5475 (6)	0.087 (2)
H17A	−0.3052	−0.0767	0.6279	0.130*
H17B	−0.2392	−0.0992	0.5224	0.130*
H17C	−0.4328	−0.0769	0.5050	0.130*
C20	−0.4657 (14)	−0.1911 (5)	−0.1900 (12)	0.190 (6)
H20A	−0.4986	−0.1768	−0.2676	0.285*
H20B	−0.3402	−0.1934	−0.1649	0.285*
H20C	−0.5090	−0.1644	−0.1410	0.285*
O1	−0.6395 (12)	−0.2727 (4)	−0.2586 (10)	0.270 (7)
C19	−0.5396 (11)	−0.2489 (4)	−0.1845 (10)	0.128 (4)
C18	−0.4935 (19)	−0.2761 (7)	−0.0704 (18)	0.282 (11)
H18A	−0.5479	−0.3143	−0.0738	0.423*
H18B	−0.5339	−0.2514	−0.0172	0.423*
H18C	−0.3684	−0.2804	−0.0456	0.423*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1211 (13)	0.0545 (8)	0.0670 (11)	−0.0223 (7)	0.0123 (8)	−0.0058 (6)
N1	0.103 (3)	0.049 (2)	0.041 (3)	−0.010 (2)	0.022 (2)	−0.0016 (18)
N2	0.089 (3)	0.046 (2)	0.050 (3)	−0.007 (2)	0.017 (2)	−0.0037 (18)
N3	0.075 (3)	0.045 (2)	0.045 (2)	0.0009 (19)	0.0128 (19)	0.0006 (18)
N4	0.077 (3)	0.044 (2)	0.041 (2)	−0.0004 (18)	0.0162 (19)	−0.0022 (17)
N5	0.085 (3)	0.050 (2)	0.046 (3)	−0.002 (2)	0.020 (2)	−0.0019 (18)
C1	0.103 (5)	0.068 (4)	0.082 (5)	−0.015 (3)	0.027 (4)	−0.022 (3)
C2	0.073 (3)	0.058 (3)	0.061 (3)	−0.005 (3)	0.023 (3)	−0.005 (3)
C3	0.089 (4)	0.070 (4)	0.059 (4)	−0.001 (3)	0.001 (3)	−0.010 (3)
C4	0.098 (4)	0.053 (3)	0.060 (4)	0.006 (3)	0.010 (3)	0.004 (3)
C5	0.074 (3)	0.047 (3)	0.058 (3)	0.001 (2)	0.020 (3)	−0.002 (2)
C6	0.073 (3)	0.052 (3)	0.058 (3)	0.007 (2)	0.015 (3)	−0.003 (2)
C7	0.089 (4)	0.046 (3)	0.070 (4)	0.004 (3)	0.027 (3)	−0.001 (2)
C8	0.069 (3)	0.047 (3)	0.040 (3)	0.003 (2)	0.014 (2)	−0.004 (2)
C9	0.072 (3)	0.041 (2)	0.055 (3)	−0.002 (2)	0.007 (2)	−0.002 (2)
C10	0.065 (3)	0.045 (2)	0.039 (3)	0.005 (2)	0.015 (2)	0.003 (2)
C11	0.059 (3)	0.053 (3)	0.052 (3)	0.002 (2)	0.012 (2)	0.008 (2)
C12	0.087 (4)	0.062 (3)	0.061 (4)	−0.011 (3)	0.021 (3)	−0.003 (3)
C13	0.092 (4)	0.063 (3)	0.074 (4)	−0.013 (3)	0.028 (3)	−0.006 (3)
C14	0.062 (3)	0.054 (3)	0.088 (4)	0.006 (2)	0.019 (3)	0.012 (3)
C15	0.100 (4)	0.064 (4)	0.072 (4)	0.003 (3)	0.022 (3)	0.020 (3)
C16	0.095 (4)	0.065 (3)	0.058 (4)	0.000 (3)	0.014 (3)	0.005 (3)
C17	0.083 (4)	0.061 (4)	0.119 (6)	−0.002 (3)	0.029 (4)	0.023 (3)
C20	0.115 (7)	0.120 (8)	0.317 (18)	−0.006 (6)	0.021 (9)	−0.032 (9)
O1	0.188 (7)	0.160 (7)	0.364 (14)	0.037 (6)	−0.122 (8)	−0.155 (8)
C19	0.088 (5)	0.097 (6)	0.171 (9)	0.018 (4)	−0.024 (5)	−0.060 (6)
C18	0.156 (11)	0.27 (2)	0.36 (3)	−0.053 (13)	−0.040 (15)	0.123 (18)

Geometric parameters (Å, º) top

Cl1—C9	1.736 (5)	C6—H6A	0.9300
N1—C8	1.350 (6)	C7—H7A	0.9300
N1—C5	1.428 (6)	C11—C12	1.389 (7)
N1—H1A	0.8600	C11—C16	1.404 (7)
N2—C9	1.337 (6)	C12—C13	1.384 (7)
N2—C8	1.353 (6)	C12—H12A	0.9300
N3—C9	1.333 (6)	C13—C14	1.396 (8)
N3—C10	1.356 (6)	C13—H13A	0.9300
N4—C8	1.356 (6)	C14—C15	1.386 (8)
N4—C10	1.359 (6)	C14—C17	1.521 (7)
N5—C10	1.364 (6)	C15—C16	1.381 (7)
N5—C11	1.414 (6)	C15—H15A	0.9300
N5—H5A	0.8600	C16—H16A	0.9300
C1—C2	1.509 (7)	C17—H17A	0.9600
C1—H1B	0.9600	C17—H17B	0.9600
C1—H1C	0.9600	C17—H17C	0.9600
C1—H1D	0.9600	C20—C19	1.436 (13)
C2—C3	1.375 (8)	C20—H20A	0.9600
C2—C7	1.397 (8)	C20—H20B	0.9600
C3—C4	1.384 (7)	C20—H20C	0.9600
C3—H3B	0.9300	O1—C19	1.164 (9)
C4—C5	1.386 (8)	C19—C18	1.463 (18)
C4—H4B	0.9300	C18—H18A	0.9600
C5—C6	1.380 (7)	C18—H18B	0.9600
C6—C7	1.385 (7)	C18—H18C	0.9600

C8—N1—C5	128.5 (4)	N4—C10—N5	120.5 (4)
C8—N1—H1A	115.8	C12—C11—C16	117.9 (5)
C5—N1—H1A	115.8	C12—C11—N5	125.2 (5)
C9—N2—C8	112.3 (4)	C16—C11—N5	116.9 (5)
C9—N3—C10	112.8 (4)	C13—C12—C11	120.1 (5)
C8—N4—C10	115.1 (4)	C13—C12—H12A	120.0
C10—N5—C11	130.4 (4)	C11—C12—H12A	120.0
C10—N5—H5A	114.8	C12—C13—C14	122.4 (5)
C11—N5—H5A	114.8	C12—C13—H13A	118.8
C2—C1—H1B	109.5	C14—C13—H13A	118.8
C2—C1—H1C	109.5	C15—C14—C13	117.2 (5)
H1B—C1—H1C	109.5	C15—C14—C17	121.5 (6)
C2—C1—H1D	109.5	C13—C14—C17	121.3 (6)
H1B—C1—H1D	109.5	C16—C15—C14	121.2 (6)
H1C—C1—H1D	109.5	C16—C15—H15A	119.4
C3—C2—C7	116.7 (5)	C14—C15—H15A	119.4
C3—C2—C1	121.8 (5)	C15—C16—C11	121.2 (6)
C7—C2—C1	121.5 (5)	C15—C16—H16A	119.4
C2—C3—C4	122.0 (5)	C11—C16—H16A	119.4
C2—C3—H3B	119.0	C14—C17—H17A	109.5
C4—C3—H3B	119.0	C14—C17—H17B	109.5
C3—C4—C5	120.2 (5)	H17A—C17—H17B	109.5
C3—C4—H4B	119.9	C14—C17—H17C	109.5
C5—C4—H4B	119.9	H17A—C17—H17C	109.5
C6—C5—C4	119.3 (5)	H17B—C17—H17C	109.5
C6—C5—N1	122.5 (5)	C19—C20—H20A	109.5
C4—C5—N1	118.1 (4)	C19—C20—H20B	109.5
C5—C6—C7	119.3 (5)	H20A—C20—H20B	109.5
C5—C6—H6A	120.3	C19—C20—H20C	109.5
C7—C6—H6A	120.3	H20A—C20—H20C	109.5
C6—C7—C2	122.4 (5)	H20B—C20—H20C	109.5
C6—C7—H7A	118.8	O1—C19—C20	126.1 (13)
C2—C7—H7A	118.8	O1—C19—C18	119.2 (13)
N1—C8—N2	115.1 (4)	C20—C19—C18	114.5 (10)
N1—C8—N4	119.5 (4)	C19—C18—H18A	109.5
N2—C8—N4	125.4 (4)	C19—C18—H18B	109.5
N3—C9—N2	129.6 (4)	H18A—C18—H18B	109.5
N3—C9—Cl1	114.7 (4)	C19—C18—H18C	109.5
N2—C9—Cl1	115.7 (4)	H18A—C18—H18C	109.5
N3—C10—N4	124.7 (4)	H18B—C18—H18C	109.5
N3—C10—N5	114.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.16	3.018 (6)	176
N5—H5A···N2ⁱⁱ	0.86	2.45	3.300 (6)	171
C4—H4B···O1ⁱⁱⁱ	0.93	2.36	3.264 (9)	165
C6—H6A···N4	0.93	2.59	2.999 (6)	107
C12—H12A···N4	0.93	2.30	2.912 (7)	123
C1—H1C···Cg1^iv	0.96	3.01	3.806 (2)	141
C17—H17C···Cg2^v	0.96	2.92	3.745 (2)	145

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x−1, y+1/2, −z−1/2; (iv) −x+1, −y, −z; (v) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClN₅·C₂H₆O
M_r	383.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8610 (16), 22.579 (5), 12.012 (2)
β (°)	104.22 (3)
V (Å³)	2066.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4122, 3833, 1855
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.329, 1.06
No. of reflections	3833
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.48

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.16	3.018 (6)	175.8
N5—H5A···N2ⁱⁱ	0.86	2.45	3.300 (6)	170.6
C4—H4B···O1ⁱⁱⁱ	0.93	2.36	3.264 (9)	165.3
C6—H6A···N4	0.93	2.59	2.999 (6)	107.2
C12—H12A···N4	0.93	2.30	2.912 (7)	122.7
C1—H1C···Cg1^iv	0.96	3.01	3.806 (2)	141
C17—H17C···Cg2^v	0.96	2.92	3.745 (2)	145

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x−1, y+1/2, −z−1/2; (iv) −x+1, −y, −z; (v) −x+1, −y, −z+1.

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