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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1744.
Published online 2008 August 13. doi:  10.1107/S1600536808025166
PMCID: PMC2960659

N 2,N 2,N 4,N 4,N 6,N 6-Hexapropyl-1,3,5-triazine-2,4,6-triamine

Abstract

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.

Related literature

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

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Object name is e-64-o1744-scheme1.jpg

Experimental

Crystal data

  • C21H42N6
  • M r = 378.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1744-efi1.jpg
  • a = 9.847 (2) Å
  • b = 12.044 (2) Å
  • c = 12.910 (3) Å
  • α = 116.57 (2)°
  • β = 96.94 (4)°
  • γ = 106.81 (3)°
  • V = 1253.7 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.06 mm−1
  • T = 295 (2) K
  • 0.32 × 0.24 × 0.13 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 [triangle]) T min = 0.981, T max = 0.992
  • 5686 measured reflections
  • 5364 independent reflections
  • 1966 reflections with I > 2σ(I)
  • R int = 0.019
  • 3 standard reflections
  • every 100 reflections
  • intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.179
  • S = 1.00
  • 5364 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.17 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025166/at2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025166/at2607Isup2.hkl

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C21H42N6Z = 2
Mr = 378.61F000 = 420
Triclinic, P1Dx = 1.003 Mg m3
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 mm1
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

Bruker P4 diffractometerRint = 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

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 Å3
5364 reflectionsΔρmin = −0.17 e Å3
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

Special details

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)

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)

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, °)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2607).

References

  • 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. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography