supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

at2607 scheme

Acta Cryst. (2008). E64, o1744    [ doi:10.1107/S1600536808025166 ]

N2,N2,N4,N4,N6,N6-Hexapropyl-1,3,5-triazine-2,4,6-triamine

Y.-F. Li and F.-F. Jian

Abstract top

The title compound, C21H42N6, was prepared by the reaction of 2,4,6-trichloro-1,3,5-triazine with dipropylamine. The structure of the molecule is tripodal.

Comment top

Triazine have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Frassanito et al., 1996). As part of our search for new triazine compounds, we synthesized the title compound (I), and describe its structure here.

In the title compound (I) (Fig. 1), the non-hydrogen atoms of the triazine ring are almost in the same plane, with a maximum deviation of 0.016 (3) Å for C19. The C20—N2 bond length of 1.361 (3)Å is comparable with C—N bond [1.334 (2) Å] reported (Bishop et al., 2002). In the structure, there is no classical hydrogen bonds.

Related literature top

For related literature, see: Frassanito et al. (1996); Bishop et al. (2002).

Experimental top

A mixture of the 2,4,6-trichloro-1,3,5-triazine (0.1 mol), and dipropylamine (0.4 mol) was stirred in refluxing ethanol (30 mL) for 5 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.96 and 0.97 Å, and with Uiso=1.2–1.5Ueq.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
N2,N2,N4,N4,N6,N6-Hexapropyl-1,3,5-triazine-2,4,6-triamine top
Crystal data top
C21H42N6Z = 2
Mr = 378.61F000 = 420
Triclinic, P1Dx = 1.003 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.847 (2) ÅCell parameters from 5779 reflections
b = 12.044 (2) Åθ = 1.9–26.8º
c = 12.910 (3) ŵ = 0.06 mm−1
α = 116.57 (2)ºT = 295 (2) K
β = 96.94 (4)ºPrism, colourless
γ = 106.81 (3)º0.32 × 0.24 × 0.13 mm
V = 1253.7 (7) Å3
Data collection top
Bruker P4
diffractometer		Rint = 0.019
Radiation source: sealed tubeθmax = 27.0º
Monochromator: graphiteθmin = 1.8º
T = 295(2) Kh = 0→11
ω scansk = −14→14
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)		l = −15→15
Tmin = 0.981, Tmax = 0.9923 standard reflections
5686 measured reflections every 100 reflections
5364 independent reflections intensity decay: none
1966 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067  1/[σ2(Fo2) + 0.5P + (0.04P)2 + sinθ/λ],
where P = 0.5Fo2 + 0.5Fc2
wR(F2) = 0.179(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.32 e Å−3
5364 reflectionsΔρmin = −0.17 e Å−3
245 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (3)
Secondary atom site location: difference Fourier map
Crystal data top
C21H42N6γ = 106.81 (3)º
Mr = 378.61V = 1253.7 (7) Å3
Triclinic, P1Z = 2
a = 9.847 (2) ÅMo Kα
b = 12.044 (2) ŵ = 0.06 mm−1
c = 12.910 (3) ÅT = 295 (2) K
α = 116.57 (2)º0.32 × 0.24 × 0.13 mm
β = 96.94 (4)º
Data collection top
Bruker P4
diffractometer		1966 reflections with I > 2σ(I)
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)		Rint = 0.019
Tmin = 0.981, Tmax = 0.9923 standard reflections
5686 measured reflections every 100 reflections
5364 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.067245 parameters
wR(F2) = 0.179H-atom parameters constrained
S = 1.00Δρmax = 0.32 e Å−3
5364 reflectionsΔρmin = −0.17 e Å−3
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
xyzUiso*/Ueq
N10.4912 (3)0.6819 (2)0.6032 (2)0.0771 (7)
N20.0405 (3)0.3446 (2)0.5011 (2)0.0786 (7)
N30.1842 (3)0.4375 (3)0.2129 (2)0.0921 (8)
N40.3388 (3)0.5651 (2)0.4067 (2)0.0706 (7)
N50.2667 (3)0.5137 (2)0.55636 (19)0.0705 (6)
N60.1080 (3)0.3826 (2)0.3515 (2)0.0713 (7)
C10.5019 (5)0.8038 (5)0.9325 (3)0.1492 (17)
H1A0.46150.86240.98560.224*
H1B0.60760.83980.96640.224*
H1C0.45950.71620.92310.224*
C20.4656 (4)0.7929 (4)0.8097 (3)0.1069 (11)
H2A0.35890.75750.77570.128*
H2B0.50690.88170.81920.128*
C30.5281 (3)0.7023 (3)0.7252 (3)0.0900 (10)
H3A0.63520.74040.75840.108*
H3B0.49090.61560.72010.108*
C40.6951 (4)0.9729 (4)0.5583 (4)0.1302 (14)
H4A0.67741.05200.57240.195*
H4B0.68830.92060.47450.195*
H4C0.79230.99870.60750.195*
C50.5798 (4)0.8894 (3)0.5909 (3)0.1069 (11)
H5A0.58560.94350.67520.128*
H5B0.48170.86500.54200.128*
C60.6005 (3)0.7640 (3)0.5718 (3)0.0853 (9)
H6A0.59460.71020.48740.102*
H6B0.69900.78880.62020.102*
C70.1670 (5)0.3639 (5)0.8037 (3)0.1554 (18)
H7A0.22220.32080.82720.233*
H7B0.07170.34070.81720.233*
H7C0.22010.45980.85100.233*
C80.1462 (5)0.3165 (4)0.6678 (3)0.1200 (13)
H8A0.24260.33800.65380.144*
H8B0.09320.21960.62000.144*
C90.0622 (4)0.3824 (3)0.6288 (3)0.0927 (10)
H9A−0.03410.35940.64260.111*
H9B0.11460.47920.67900.111*
C10−0.2179 (5)−0.0011 (4)0.2490 (4)0.1599 (18)
H10A−0.2036−0.08410.20940.240*
H10B−0.24020.02540.19120.240*
H10C−0.2987−0.01330.28300.240*
C11−0.0829 (4)0.1031 (4)0.3453 (3)0.1207 (13)
H11A−0.00130.11390.31070.145*
H11B−0.05960.07490.40240.145*
C12−0.0979 (3)0.2375 (3)0.4121 (3)0.0880 (9)
H12A−0.12980.26180.35390.106*
H12B−0.17370.22860.45260.106*
C13−0.1129 (5)0.1115 (4)−0.0532 (4)0.1646 (19)
H13A−0.11140.0240−0.10080.247*
H13B−0.12990.1473−0.10450.247*
H13C−0.19100.1045−0.01570.247*
C140.0419 (5)0.2090 (4)0.0485 (4)0.1355 (15)
H14A0.06060.17270.09990.163*
H14B0.12130.21670.01130.163*
C150.0374 (4)0.3384 (4)0.1194 (3)0.1107 (12)
H15A−0.03910.33050.15940.133*
H15B0.01220.37140.06660.133*
C160.4074 (6)0.7152 (5)0.1645 (5)0.194 (2)
H16A0.39640.79630.17620.291*
H16B0.40370.66100.08180.291*
H16C0.50100.73760.21690.291*
C170.2822 (5)0.6369 (4)0.1941 (4)0.1364 (15)
H17A0.28530.69160.27750.164*
H17B0.18750.61550.14230.164*
C180.2973 (4)0.5110 (3)0.1757 (3)0.1099 (12)
H18A0.28670.45370.09090.132*
H18B0.39550.53240.22240.132*
C190.3614 (3)0.5835 (3)0.5187 (3)0.0672 (7)
C200.1420 (3)0.4161 (3)0.4683 (3)0.0672 (7)
C210.2109 (4)0.4625 (3)0.3276 (2)0.0689 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0721 (17)0.0766 (16)0.0648 (16)0.0163 (14)0.0150 (14)0.0306 (13)
N20.0749 (17)0.0800 (17)0.0733 (16)0.0149 (14)0.0245 (14)0.0413 (14)
N30.096 (2)0.0876 (18)0.0616 (16)0.0011 (16)0.0113 (15)0.0375 (14)
N40.0734 (17)0.0688 (15)0.0576 (14)0.0195 (14)0.0176 (13)0.0279 (12)
N50.0706 (16)0.0686 (15)0.0648 (15)0.0181 (13)0.0186 (14)0.0336 (13)
N60.0726 (17)0.0701 (15)0.0659 (16)0.0193 (13)0.0201 (12)0.0353 (13)
C10.172 (4)0.183 (4)0.082 (3)0.065 (4)0.041 (3)0.060 (3)
C20.108 (3)0.110 (3)0.089 (2)0.042 (2)0.026 (2)0.041 (2)
C30.074 (2)0.089 (2)0.082 (2)0.0237 (18)0.0119 (17)0.0308 (18)
C40.128 (3)0.117 (3)0.176 (4)0.043 (3)0.064 (3)0.096 (3)
C50.110 (3)0.100 (3)0.127 (3)0.045 (2)0.047 (2)0.065 (2)
C60.064 (2)0.085 (2)0.092 (2)0.0170 (17)0.0177 (17)0.0406 (18)
C70.208 (5)0.207 (5)0.107 (3)0.106 (4)0.065 (3)0.104 (3)
C80.142 (4)0.133 (3)0.119 (3)0.072 (3)0.055 (3)0.075 (3)
C90.090 (2)0.103 (2)0.107 (3)0.039 (2)0.046 (2)0.066 (2)
C100.134 (4)0.112 (3)0.163 (4)0.019 (3)0.011 (3)0.039 (3)
C110.099 (3)0.094 (3)0.127 (3)0.010 (2)0.003 (2)0.046 (2)
C120.074 (2)0.084 (2)0.098 (2)0.0205 (18)0.0306 (19)0.045 (2)
C130.134 (4)0.126 (3)0.122 (3)0.009 (3)−0.016 (3)0.013 (3)
C140.142 (4)0.134 (4)0.134 (3)0.065 (3)0.048 (3)0.061 (3)
C150.143 (4)0.098 (3)0.091 (3)0.041 (3)0.043 (3)0.049 (2)
C160.199 (5)0.192 (5)0.210 (5)0.022 (4)0.079 (5)0.145 (5)
C170.135 (4)0.155 (4)0.142 (4)0.049 (3)0.046 (3)0.096 (3)
C180.144 (3)0.092 (3)0.075 (2)0.026 (2)0.019 (2)0.043 (2)
C190.071 (2)0.0604 (17)0.0604 (18)0.0230 (16)0.0166 (16)0.0252 (15)
C200.072 (2)0.0647 (18)0.069 (2)0.0267 (16)0.0256 (17)0.0355 (16)
C210.080 (2)0.0698 (18)0.0536 (17)0.0290 (17)0.0182 (16)0.0295 (15)
Geometric parameters (Å, °) top
N1—C191.363 (3)C7—H7B0.9600
N1—C31.462 (3)C7—H7C0.9600
N1—C61.466 (3)C8—C91.485 (4)
N2—C201.361 (3)C8—H8A0.9700
N2—C121.456 (4)C8—H8B0.9700
N2—C91.469 (4)C9—H9A0.9700
N3—C211.346 (3)C9—H9B0.9700
N3—C181.481 (4)C10—C111.458 (5)
N3—C151.505 (4)C10—H10A0.9600
N4—C191.339 (3)C10—H10B0.9600
N4—C211.348 (3)C10—H10C0.9600
N5—C201.347 (3)C11—C121.518 (4)
N5—C191.355 (3)C11—H11A0.9700
N6—C211.350 (3)C11—H11B0.9700
N6—C201.343 (3)C12—H12A0.9700
C1—C21.520 (4)C12—H12B0.9700
C1—H1A0.9600C13—C141.590 (5)
C1—H1B0.9600C13—H13A0.9600
C1—H1C0.9600C13—H13B0.9600
C2—C31.499 (4)C13—H13C0.9600
C2—H2A0.9700C14—C151.429 (5)
C2—H2B0.9700C14—H14A0.9700
C3—H3A0.9700C14—H14B0.9700
C3—H3B0.9700C15—H15A0.9700
C4—C51.520 (4)C15—H15B0.9700
C4—H4A0.9600C16—C171.522 (5)
C4—H4B0.9600C16—H16A0.9600
C4—H4C0.9600C16—H16B0.9600
C5—C61.496 (4)C16—H16C0.9600
C5—H5A0.9700C17—C181.482 (5)
C5—H5B0.9700C17—H17A0.9700
C6—H6A0.9700C17—H17B0.9700
C6—H6B0.9700C18—H18A0.9700
C7—C81.548 (4)C18—H18B0.9700
C7—H7A0.9600
C19—N1—C3120.5 (3)H9A—C9—H9B107.6
C19—N1—C6120.8 (2)C11—C10—H10A109.5
C3—N1—C6118.5 (2)C11—C10—H10B109.5
C20—N2—C12120.5 (2)H10A—C10—H10B109.5
C20—N2—C9120.5 (3)C11—C10—H10C109.5
C12—N2—C9118.8 (2)H10A—C10—H10C109.5
C21—N3—C18120.8 (3)H10B—C10—H10C109.5
C21—N3—C15121.6 (3)C10—C11—C12112.3 (3)
C18—N3—C15117.5 (3)C10—C11—H11A109.2
C19—N4—C21113.6 (2)C12—C11—H11A109.2
C20—N5—C19113.8 (2)C10—C11—H11B109.2
C21—N6—C20113.2 (2)C12—C11—H11B109.2
C2—C1—H1A109.5H11A—C11—H11B107.9
C2—C1—H1B109.5N2—C12—C11112.4 (3)
H1A—C1—H1B109.5N2—C12—H12A109.1
C2—C1—H1C109.5C11—C12—H12A109.1
H1A—C1—H1C109.5N2—C12—H12B109.1
H1B—C1—H1C109.5C11—C12—H12B109.1
C3—C2—C1110.5 (3)H12A—C12—H12B107.8
C3—C2—H2A109.6C14—C13—H13A109.5
C1—C2—H2A109.6C14—C13—H13B109.5
C3—C2—H2B109.6H13A—C13—H13B109.5
C1—C2—H2B109.6C14—C13—H13C109.5
H2A—C2—H2B108.1H13A—C13—H13C109.5
N1—C3—C2113.4 (3)H13B—C13—H13C109.5
N1—C3—H3A108.9C15—C14—C13108.8 (4)
C2—C3—H3A108.9C15—C14—H14A109.9
N1—C3—H3B108.9C13—C14—H14A109.9
C2—C3—H3B108.9C15—C14—H14B109.9
H3A—C3—H3B107.7C13—C14—H14B109.9
C5—C4—H4A109.5H14A—C14—H14B108.3
C5—C4—H4B109.5C14—C15—N3111.3 (3)
H4A—C4—H4B109.5C14—C15—H15A109.4
C5—C4—H4C109.5N3—C15—H15A109.4
H4A—C4—H4C109.5C14—C15—H15B109.4
H4B—C4—H4C109.5N3—C15—H15B109.4
C6—C5—C4112.6 (3)H15A—C15—H15B108.0
C6—C5—H5A109.1C17—C16—H16A109.5
C4—C5—H5A109.1C17—C16—H16B109.5
C6—C5—H5B109.1H16A—C16—H16B109.5
C4—C5—H5B109.1C17—C16—H16C109.5
H5A—C5—H5B107.8H16A—C16—H16C109.5
N1—C6—C5113.8 (3)H16B—C16—H16C109.5
N1—C6—H6A108.8C18—C17—C16110.0 (4)
C5—C6—H6A108.8C18—C17—H17A109.7
N1—C6—H6B108.8C16—C17—H17A109.7
C5—C6—H6B108.8C18—C17—H17B109.7
H6A—C6—H6B107.7C16—C17—H17B109.7
C8—C7—H7A109.5H17A—C17—H17B108.2
C8—C7—H7B109.5N3—C18—C17111.5 (3)
H7A—C7—H7B109.5N3—C18—H18A109.3
C8—C7—H7C109.5C17—C18—H18A109.3
H7A—C7—H7C109.5N3—C18—H18B109.3
H7B—C7—H7C109.5C17—C18—H18B109.3
C9—C8—C7110.8 (3)H18A—C18—H18B108.0
C9—C8—H8A109.5N4—C19—N5126.1 (3)
C7—C8—H8A109.5N4—C19—N1117.3 (3)
C9—C8—H8B109.5N5—C19—N1116.6 (3)
C7—C8—H8B109.5N5—C20—N6126.5 (3)
H8A—C8—H8B108.1N5—C20—N2116.6 (3)
N2—C9—C8114.1 (3)N6—C20—N2116.9 (3)
N2—C9—H9A108.7N6—C21—N3117.1 (3)
C8—C9—H9A108.7N6—C21—N4126.8 (3)
N2—C9—H9B108.7N3—C21—N4116.1 (3)
C8—C9—H9B108.7
references
References top

Bishop, M. M., Lindoy, L. F. & Skelton, B. W. (2002). J. Chem. Soc., Dalton Trans. pp. 377–382.

Bruker, (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.

Frassanito, R., De Socio, G., Laura, D. & Rotilio, D. (1996). J. Agric. Food Chem. 44, 2282–2286.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.