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The title compound, C15H26ClN5O, was synthesized by the reaction of 2,4,6-trichloro-1,3,5-triazine with 2,4,4-trimethyl­pentan-2-amine and morpholine. The triazine ring is planar and the morpholine ring displays a typical chair conformation. Inter­molecular N—H...O hydrogen bonding is present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027924/xu2270sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027924/xu2270Isup2.hkl
Contains datablock I

CCDC reference: 655597

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.114
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound is an important intermediate of hindered light stabilizers (Borzatta & Carrozza, 1991). These compounds containing triazine ring are widely used (Deng et al., 2006). We report here the crystal structure of the title compound (Fig. 1). The triazine ring in the title compound is essentially planar with an r.m.s. deviation from the mean plane of 0.009 Å.

Related literature top

For general backgroud, see Borzatta & Carrozza (1991). For a related structure, see Deng et al. (2006). For synthesis, see Kaiser & Thurston (1951).

Experimental top

The title compound was prepared according to the method of Kaiser & Thurston (1951). 2,4,6-Trichloro-1,3,5-triazine (40.0 g, 0.217 mol) was dissolved in toluene (120 ml) and then cooled to 278 K. With stirring, a solution of 2,4,4-trimethylpentan-2-amine (27.5 g, 0.213 mol) in toluene (50 ml) was added dropwise to the mixture over a period of 0.5 h. Then a solution of Na2CO3 (23.02 g, 0.217 mol) in water (50 ml) was added dropwise for 0.5 h. The mixture was stirred at 273–278 K for a further 3 h. Morpholine (18.9 g, 0.217 mol) and solid Na2CO3 (23.02 g, 0.217 mol) were added to the mixture, keeping temperature at 338 k for 5 h. The title compound (54.91 g) was obtained in powder form in a yield of 78.6%. Single crystals of the title compound were obtained by slow evaporation of a methanol solution.

Refinement top

Imino H4 atom was located in a difference Fourier map and isotropically refined with a restraint of O—H = 0.90±0.01 Å. Other H atoms were positioned geometrically with C—H = 0.96–0.97 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(C) for methyl groups or 1.2Ueq(C) for others.

Structure description top

The title compound is an important intermediate of hindered light stabilizers (Borzatta & Carrozza, 1991). These compounds containing triazine ring are widely used (Deng et al., 2006). We report here the crystal structure of the title compound (Fig. 1). The triazine ring in the title compound is essentially planar with an r.m.s. deviation from the mean plane of 0.009 Å.

For general backgroud, see Borzatta & Carrozza (1991). For a related structure, see Deng et al. (2006). For synthesis, see Kaiser & Thurston (1951).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The unit cell packing diagram of the title compound.
4-Chloro-6-morpholino-N2-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine top
Crystal data top
C15H26ClN5OF(000) = 704
Mr = 327.86Dx = 1.231 Mg m3
Monoclinic, P21/nMelting point = 369–371 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.119 (3) ÅCell parameters from 2545 reflections
b = 7.4964 (17) Åθ = 2.9–24.5°
c = 17.083 (4) ŵ = 0.23 mm1
β = 101.939 (4)°T = 294 K
V = 1769.0 (7) Å3Prism, colourless
Z = 40.24 × 0.18 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 26.7°, θmin = 1.7°
φ and ω scansh = 1617
9840 measured reflectionsk = 79
3618 independent reflectionsl = 2117
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2056P]
where P = (Fo2 + 2Fc2)/3
3618 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C15H26ClN5OV = 1769.0 (7) Å3
Mr = 327.86Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.119 (3) ŵ = 0.23 mm1
b = 7.4964 (17) ÅT = 294 K
c = 17.083 (4) Å0.24 × 0.18 × 0.12 mm
β = 101.939 (4)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2385 reflections with I > 2σ(I)
9840 measured reflectionsRint = 0.035
3618 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.15 e Å3
3618 reflectionsΔρmin = 0.22 e Å3
208 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
xyzUiso*/Ueq
Cl10.43258 (4)0.68022 (8)1.16149 (3)0.05564 (19)
O10.31616 (10)0.8309 (2)0.72604 (8)0.0534 (4)
N10.43414 (11)0.7080 (2)1.01064 (9)0.0402 (4)
N20.58416 (11)0.7425 (2)1.10318 (8)0.0385 (4)
N30.57800 (10)0.7775 (2)0.96303 (8)0.0385 (4)
N40.72149 (11)0.8004 (2)1.05739 (9)0.0419 (4)
N50.43047 (11)0.7482 (2)0.87630 (9)0.0466 (4)
C10.48256 (13)0.7441 (2)0.95198 (10)0.0368 (4)
C20.49106 (13)0.7137 (2)1.08183 (11)0.0373 (4)
C30.62534 (12)0.7724 (2)1.03887 (10)0.0344 (4)
C40.47478 (15)0.7818 (3)0.80787 (11)0.0532 (6)
H4A0.48370.66990.78180.064*
H4B0.53780.83660.82570.064*
C50.41114 (15)0.9024 (3)0.75028 (12)0.0528 (5)
H5A0.40751.01780.77520.063*
H5B0.43920.91970.70360.063*
C60.27284 (14)0.8130 (3)0.79388 (12)0.0518 (5)
H6A0.20750.76750.77680.062*
H6B0.26880.92940.81780.062*
C70.32985 (14)0.6891 (3)0.85542 (12)0.0506 (5)
H7A0.30220.68830.90290.061*
H7B0.32690.56880.83420.061*
C80.78825 (13)0.8290 (3)1.00235 (10)0.0390 (4)
C90.88419 (15)0.8807 (3)1.05725 (13)0.0624 (6)
H9A0.87390.97981.09010.094*
H9B0.93000.91371.02540.094*
H9C0.90880.78121.09070.094*
C100.75325 (16)0.9854 (3)0.94675 (13)0.0574 (6)
H10A0.69520.95210.90960.086*
H10B0.80241.01690.91790.086*
H10C0.74011.08580.97780.086*
C110.79641 (13)0.6485 (2)0.96018 (11)0.0400 (4)
H11A0.73110.60170.94510.048*
H11B0.83150.56881.00080.048*
C120.84258 (13)0.6268 (3)0.88572 (11)0.0458 (5)
C130.85638 (17)0.4252 (3)0.87652 (14)0.0687 (7)
H13A0.79550.36560.87320.103*
H13B0.90220.38130.92200.103*
H13C0.88010.40280.82870.103*
C140.94073 (16)0.7175 (3)0.89346 (15)0.0703 (7)
H14A0.96720.68970.84750.105*
H14B0.98380.67570.94090.105*
H14C0.93290.84430.89680.105*
C150.77405 (17)0.6911 (3)0.80975 (12)0.0640 (6)
H15A0.77010.81890.81040.096*
H15B0.71090.64120.80730.096*
H15C0.79810.65360.76380.096*
H40.7492 (13)0.778 (2)1.1082 (6)0.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0497 (3)0.0763 (4)0.0457 (3)0.0021 (3)0.0209 (2)0.0055 (3)
O10.0470 (8)0.0700 (10)0.0372 (7)0.0010 (7)0.0050 (6)0.0001 (7)
N10.0337 (8)0.0479 (10)0.0386 (9)0.0018 (7)0.0062 (7)0.0017 (7)
N20.0345 (9)0.0487 (10)0.0317 (8)0.0000 (7)0.0058 (7)0.0015 (7)
N30.0315 (8)0.0501 (10)0.0325 (8)0.0008 (7)0.0029 (6)0.0006 (7)
N40.0319 (8)0.0616 (11)0.0310 (8)0.0034 (7)0.0036 (7)0.0017 (8)
N50.0317 (9)0.0696 (12)0.0356 (9)0.0029 (8)0.0001 (7)0.0061 (8)
C10.0362 (10)0.0365 (10)0.0362 (10)0.0020 (8)0.0044 (8)0.0018 (8)
C20.0388 (10)0.0379 (11)0.0369 (10)0.0012 (8)0.0114 (8)0.0008 (8)
C30.0320 (9)0.0380 (11)0.0325 (9)0.0006 (8)0.0053 (8)0.0019 (8)
C40.0396 (11)0.0823 (17)0.0363 (11)0.0022 (10)0.0048 (9)0.0043 (11)
C50.0512 (13)0.0620 (14)0.0416 (11)0.0059 (10)0.0012 (9)0.0019 (10)
C60.0386 (11)0.0620 (14)0.0497 (12)0.0023 (10)0.0029 (9)0.0047 (11)
C70.0397 (11)0.0608 (14)0.0461 (11)0.0087 (10)0.0032 (9)0.0011 (10)
C80.0326 (9)0.0482 (12)0.0367 (10)0.0047 (8)0.0082 (8)0.0016 (9)
C90.0423 (12)0.0892 (18)0.0562 (13)0.0200 (12)0.0114 (10)0.0147 (13)
C100.0591 (14)0.0479 (14)0.0699 (14)0.0007 (10)0.0244 (11)0.0082 (11)
C110.0342 (10)0.0456 (12)0.0396 (10)0.0004 (8)0.0061 (8)0.0061 (9)
C120.0399 (11)0.0559 (14)0.0432 (11)0.0027 (9)0.0119 (9)0.0034 (10)
C130.0656 (15)0.0692 (17)0.0730 (16)0.0102 (13)0.0182 (12)0.0128 (13)
C140.0497 (14)0.099 (2)0.0697 (16)0.0147 (13)0.0286 (12)0.0141 (14)
C150.0684 (15)0.0829 (18)0.0412 (12)0.0026 (13)0.0122 (11)0.0033 (12)
Geometric parameters (Å, º) top
Cl1—C21.7497 (18)C8—C101.526 (3)
O1—C51.424 (2)C8—C91.530 (3)
O1—C61.424 (2)C8—C111.548 (3)
N1—C21.312 (2)C9—H9A0.9600
N1—C11.352 (2)C9—H9B0.9600
N2—C21.307 (2)C9—H9C0.9600
N2—C31.364 (2)C10—H10A0.9600
N3—C31.330 (2)C10—H10B0.9600
N3—C11.345 (2)C10—H10C0.9600
N4—C31.345 (2)C11—C121.553 (2)
N4—C81.478 (2)C11—H11A0.9700
N4—H40.891 (9)C11—H11B0.9700
N5—C11.349 (2)C12—C141.525 (3)
N5—C41.457 (2)C12—C151.528 (3)
N5—C71.460 (2)C12—C131.536 (3)
C4—C51.493 (3)C13—H13A0.9600
C4—H4A0.9700C13—H13B0.9600
C4—H4B0.9700C13—H13C0.9600
C5—H5A0.9700C14—H14A0.9600
C5—H5B0.9700C14—H14B0.9600
C6—C71.505 (3)C14—H14C0.9600
C6—H6A0.9700C15—H15A0.9600
C6—H6B0.9700C15—H15B0.9600
C7—H7A0.9700C15—H15C0.9600
C7—H7B0.9700
C5—O1—C6109.63 (14)N4—C8—C11106.76 (14)
C2—N1—C1111.93 (15)C10—C8—C11115.32 (15)
C2—N2—C3111.97 (15)C9—C8—C11111.43 (16)
C3—N3—C1114.73 (15)C8—C9—H9A109.5
C3—N4—C8128.20 (14)C8—C9—H9B109.5
C3—N4—H4114.7 (13)H9A—C9—H9B109.5
C8—N4—H4116.0 (13)C8—C9—H9C109.5
C1—N5—C4122.23 (16)H9A—C9—H9C109.5
C1—N5—C7122.48 (16)H9B—C9—H9C109.5
C4—N5—C7114.44 (15)C8—C10—H10A109.5
N3—C1—N5117.51 (16)C8—C10—H10B109.5
N3—C1—N1125.37 (16)H10A—C10—H10B109.5
N5—C1—N1117.12 (16)C8—C10—H10C109.5
N2—C2—N1130.66 (17)H10A—C10—H10C109.5
N2—C2—Cl1114.57 (14)H10B—C10—H10C109.5
N1—C2—Cl1114.77 (14)C8—C11—C12123.87 (15)
N3—C3—N4120.26 (16)C8—C11—H11A106.4
N3—C3—N2125.28 (16)C12—C11—H11A106.4
N4—C3—N2114.46 (15)C8—C11—H11B106.4
N5—C4—C5109.48 (16)C12—C11—H11B106.4
N5—C4—H4A109.8H11A—C11—H11B106.4
C5—C4—H4A109.8C14—C12—C15109.72 (19)
N5—C4—H4B109.8C14—C12—C13108.39 (18)
C5—C4—H4B109.8C15—C12—C13107.16 (19)
H4A—C4—H4B108.2C14—C12—C11114.21 (17)
O1—C5—C4111.46 (18)C15—C12—C11111.30 (16)
O1—C5—H5A109.3C13—C12—C11105.71 (16)
C4—C5—H5A109.3C12—C13—H13A109.5
O1—C5—H5B109.3C12—C13—H13B109.5
C4—C5—H5B109.3H13A—C13—H13B109.5
H5A—C5—H5B108.0C12—C13—H13C109.5
O1—C6—C7111.63 (16)H13A—C13—H13C109.5
O1—C6—H6A109.3H13B—C13—H13C109.5
C7—C6—H6A109.3C12—C14—H14A109.5
O1—C6—H6B109.3C12—C14—H14B109.5
C7—C6—H6B109.3H14A—C14—H14B109.5
H6A—C6—H6B108.0C12—C14—H14C109.5
N5—C7—C6109.64 (17)H14A—C14—H14C109.5
N5—C7—H7A109.7H14B—C14—H14C109.5
C6—C7—H7A109.7C12—C15—H15A109.5
N5—C7—H7B109.7C12—C15—H15B109.5
C6—C7—H7B109.7H15A—C15—H15B109.5
H7A—C7—H7B108.2C12—C15—H15C109.5
N4—C8—C10109.89 (15)H15A—C15—H15C109.5
N4—C8—C9104.31 (14)H15B—C15—H15C109.5
C10—C8—C9108.56 (17)
C3—N3—C1—N5179.69 (17)C1—N5—C4—C5139.1 (2)
C3—N3—C1—N10.3 (3)C7—N5—C4—C551.2 (2)
C4—N5—C1—N31.9 (3)C6—O1—C5—C461.8 (2)
C7—N5—C1—N3170.86 (17)N5—C4—C5—O156.2 (2)
C4—N5—C1—N1178.61 (17)C5—O1—C6—C760.6 (2)
C7—N5—C1—N19.7 (3)C1—N5—C7—C6140.15 (19)
C2—N1—C1—N31.7 (3)C4—N5—C7—C650.1 (2)
C2—N1—C1—N5177.68 (17)O1—C6—C7—N554.1 (2)
C3—N2—C2—N10.7 (3)C3—N4—C8—C1055.6 (2)
C3—N2—C2—Cl1178.35 (12)C3—N4—C8—C9171.8 (2)
C1—N1—C2—N22.3 (3)C3—N4—C8—C1170.1 (2)
C1—N1—C2—Cl1176.73 (13)N4—C8—C11—C12167.39 (15)
C1—N3—C3—N4178.78 (17)C10—C8—C11—C1245.0 (2)
C1—N3—C3—N22.2 (3)C9—C8—C11—C1279.3 (2)
C8—N4—C3—N33.7 (3)C8—C11—C12—C1448.2 (3)
C8—N4—C3—N2177.19 (17)C8—C11—C12—C1576.7 (2)
C2—N2—C3—N31.8 (3)C8—C11—C12—C13167.27 (18)
C2—N2—C3—N4179.15 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.89 (1)2.20 (1)3.076 (2)169 (2)
Symmetry code: (i) x+1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H26ClN5O
Mr327.86
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)14.119 (3), 7.4964 (17), 17.083 (4)
β (°) 101.939 (4)
V3)1769.0 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.24 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9840, 3618, 2385
Rint0.035
(sin θ/λ)max1)0.632
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.114, 1.00
No. of reflections3618
No. of parameters208
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.891 (9)2.197 (10)3.076 (2)168.9 (17)
Symmetry code: (i) x+1/2, y+3/2, z+1/2.
 

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