4,6-Dimorpholino-N-(2,4,4-trimethyl­pentan-2-yl)-1,3,5-triazin-2-amine

In the title compound, C₁₉H₃₄N₆O₂, both morpholine rings adopt chair conformations. In the crystal structure, N—H...N hydrogen bonds link the mol­ecules into chains along c.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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S1. Comment

The title compound (I) is an important intermediate in the preparation of hindered light stabilizers(Borzatta & Carrozza, 1991). Compounds containing a triazine ring are widely used in polymers, dyes, drugs and hindered amine light stabilizers (Deng et al., 2006). We report here the crystal structure of the title compound (I) (Fig. 1). In (I) both morpholine rings adopt a chair conformation and the triazine ring is essentially planar with an r.m.s. deviation from the mean plane of 0.0105 Å. In the crystal N6—H6C···N1 hydrogen bonds link the molecules into chains along c, Table 1.

Related literature

For the preparation and uses of the title compound and similar compounds, see: Borzatta & Carrozza (1991); Deng et al. (2006); Kaiser & Thurston (1951).

S2. Experimental

The title compound was prepared according to the method of Kaiser & Thurston (1951) in 71% yield. Crystals of (I) were obtained by slow evaporation of a solution in methanol (m.p. 431–433 K).

S3. Refinement

The amine H atom was located in a Fourier map and was refined freely with an isotropic displacement parameter. All other H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.97 Å, U_iso = 1.2U_eq (C) for CH₂ and 0.96 Å, U_iso = 1.5U_eq (C) for CH₃ atoms.

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Bruker, 1997).

Figures

Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

4,6-Dimorpholino-N-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine

Crystal data

C19H34N6O2	F(000) = 824
Mr = 378.52	Dx = 1.217 Mg m^−3
Monoclinic, P21/c	Melting point: 431-433 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.247 (2) Å	Cell parameters from 5929 reflections
b = 16.718 (3) Å	θ = 2.1–27.9°
c = 12.107 (2) Å	µ = 0.08 mm^−1
β = 94.82 (3)°	T = 113 K
V = 2066.6 (7) Å^3	Block, colorless
Z = 4	0.08 × 0.08 × 0.02 mm

Data collection

Rigaku Saturn CCD diffractometer	3641 independent reflections
Radiation source: rotating anode	3159 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.034
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −12→12
Tmin = 0.984, Tmax = 0.998	k = −18→19
20763 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.0832P] where P = (Fo^2 + 2Fc^2)/3
3641 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.27 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.82017 (9)	0.02524 (5)	0.97507 (7)	0.0292 (2)
O2	0.14099 (9)	0.33956 (6)	0.65039 (9)	0.0375 (3)
N1	0.55524 (10)	0.20367 (6)	0.72321 (8)	0.0181 (2)
N2	0.70950 (10)	0.14783 (6)	0.60724 (8)	0.0173 (2)
N3	0.54840 (9)	0.24124 (6)	0.53212 (8)	0.0170 (2)
N4	0.70730 (10)	0.11069 (6)	0.79018 (8)	0.0203 (2)
N5	0.40537 (10)	0.29537 (6)	0.64901 (8)	0.0235 (3)
N6	0.69655 (10)	0.18699 (6)	0.42305 (8)	0.0173 (2)
C1	0.65477 (11)	0.15522 (7)	0.70307 (9)	0.0166 (3)
C2	0.65151 (11)	0.19201 (7)	0.52442 (9)	0.0156 (3)
C3	0.50656 (11)	0.24526 (7)	0.63360 (9)	0.0165 (3)
C4	0.63464 (13)	0.09771 (7)	0.88701 (10)	0.0218 (3)
H4A	0.5807	0.0502	0.8762	0.026*
H4B	0.5775	0.1429	0.8968	0.026*
C5	0.72851 (14)	0.08778 (8)	0.98842 (10)	0.0273 (3)
H5A	0.7754	0.1375	1.0033	0.033*
H5B	0.6796	0.0760	1.0517	0.033*
C6	0.89372 (13)	0.04203 (8)	0.88310 (11)	0.0275 (3)
H6A	0.9564	−0.0007	0.8754	0.033*
H6B	0.9423	0.0913	0.8971	0.033*
C7	0.80720 (12)	0.05017 (7)	0.77602 (10)	0.0227 (3)
H7A	0.8596	0.0657	0.7165	0.027*
H7B	0.7659	−0.0007	0.7568	0.027*
C8	0.34451 (13)	0.30169 (8)	0.75292 (11)	0.0275 (3)
H8A	0.3591	0.3547	0.7840	0.033*
H8B	0.3832	0.2630	0.8056	0.033*
C9	0.19977 (14)	0.28629 (9)	0.73206 (13)	0.0362 (4)
H9A	0.1857	0.2315	0.7073	0.043*
H9B	0.1584	0.2930	0.8006	0.043*
C10	0.19844 (13)	0.32924 (9)	0.54852 (12)	0.0308 (3)
H10A	0.1570	0.3654	0.4936	0.037*
H10B	0.1828	0.2750	0.5222	0.037*
C11	0.34334 (12)	0.34494 (8)	0.56048 (10)	0.0233 (3)
H11A	0.3806	0.3328	0.4913	0.028*
H11B	0.3594	0.4010	0.5775	0.028*
C12	0.81655 (11)	0.14606 (7)	0.39230 (10)	0.0191 (3)
C13	0.82342 (13)	0.16201 (8)	0.26896 (10)	0.0254 (3)
H13A	0.7446	0.1432	0.2287	0.038*
H13B	0.8974	0.1344	0.2435	0.038*
H13C	0.8325	0.2184	0.2569	0.038*
C14	0.93531 (12)	0.18489 (8)	0.45587 (11)	0.0267 (3)
H14A	0.9350	0.2413	0.4411	0.040*
H14B	1.0141	0.1616	0.4326	0.040*
H14C	0.9314	0.1762	0.5339	0.040*
C15	0.81944 (12)	0.05571 (7)	0.42141 (10)	0.0195 (3)
H15A	0.9057	0.0364	0.4071	0.023*
H15B	0.8142	0.0521	0.5009	0.023*
C16	0.71964 (12)	−0.00559 (7)	0.36787 (10)	0.0236 (3)
C17	0.71755 (15)	−0.07566 (8)	0.44923 (12)	0.0337 (3)
H17A	0.6604	−0.1167	0.4178	0.051*
H17B	0.6864	−0.0574	0.5174	0.051*
H17C	0.8045	−0.0968	0.4634	0.051*
C18	0.76316 (15)	−0.03851 (8)	0.25880 (11)	0.0345 (4)
H18A	0.7000	−0.0767	0.2284	0.052*
H18B	0.8468	−0.0641	0.2724	0.052*
H18C	0.7700	0.0046	0.2072	0.052*
C19	0.58034 (13)	0.02736 (8)	0.34862 (12)	0.0323 (3)
H19A	0.5780	0.0686	0.2933	0.048*
H19B	0.5539	0.0492	0.4166	0.048*
H19C	0.5217	−0.0150	0.3239	0.048*
H6C	0.6524 (12)	0.2176 (7)	0.3734 (9)	0.022 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0367 (5)	0.0304 (5)	0.0197 (5)	0.0065 (4)	−0.0024 (4)	0.0063 (4)
O2	0.0223 (5)	0.0435 (6)	0.0477 (7)	0.0075 (4)	0.0092 (5)	0.0084 (5)
N1	0.0206 (5)	0.0188 (5)	0.0151 (5)	0.0024 (4)	0.0018 (4)	0.0003 (4)
N2	0.0190 (5)	0.0187 (5)	0.0142 (5)	0.0010 (4)	0.0009 (4)	0.0005 (4)
N3	0.0170 (5)	0.0180 (5)	0.0161 (5)	0.0004 (4)	0.0014 (4)	0.0006 (4)
N4	0.0236 (6)	0.0220 (5)	0.0152 (5)	0.0047 (4)	0.0016 (4)	0.0023 (4)
N5	0.0224 (6)	0.0300 (6)	0.0186 (6)	0.0097 (5)	0.0054 (4)	0.0041 (4)
N6	0.0194 (5)	0.0192 (5)	0.0134 (5)	0.0038 (4)	0.0022 (4)	0.0024 (4)
C1	0.0186 (6)	0.0163 (6)	0.0148 (6)	−0.0019 (5)	−0.0004 (5)	−0.0009 (5)
C2	0.0160 (6)	0.0149 (6)	0.0157 (6)	−0.0029 (5)	0.0004 (5)	−0.0005 (5)
C3	0.0161 (6)	0.0170 (6)	0.0165 (6)	−0.0018 (5)	0.0013 (5)	−0.0008 (5)
C4	0.0286 (7)	0.0219 (7)	0.0152 (6)	0.0022 (5)	0.0041 (5)	0.0010 (5)
C5	0.0391 (8)	0.0251 (7)	0.0171 (7)	0.0033 (6)	−0.0005 (6)	−0.0001 (5)
C6	0.0266 (7)	0.0298 (7)	0.0253 (7)	0.0025 (6)	−0.0018 (6)	0.0052 (6)
C7	0.0244 (7)	0.0234 (7)	0.0203 (7)	0.0051 (5)	0.0010 (5)	0.0010 (5)
C8	0.0304 (7)	0.0301 (7)	0.0235 (7)	0.0097 (6)	0.0103 (6)	0.0011 (6)
C9	0.0323 (8)	0.0360 (8)	0.0425 (9)	0.0045 (6)	0.0165 (7)	0.0083 (7)
C10	0.0254 (7)	0.0312 (8)	0.0348 (8)	0.0023 (6)	−0.0029 (6)	−0.0010 (6)
C11	0.0239 (7)	0.0227 (7)	0.0234 (7)	0.0063 (5)	0.0021 (5)	0.0031 (5)
C12	0.0177 (6)	0.0215 (6)	0.0185 (6)	0.0022 (5)	0.0042 (5)	0.0006 (5)
C13	0.0288 (7)	0.0270 (7)	0.0216 (7)	0.0064 (6)	0.0092 (6)	0.0039 (5)
C14	0.0219 (7)	0.0275 (7)	0.0310 (8)	−0.0024 (5)	0.0045 (6)	−0.0004 (6)
C15	0.0191 (6)	0.0221 (7)	0.0174 (6)	0.0055 (5)	0.0019 (5)	0.0013 (5)
C16	0.0254 (7)	0.0208 (7)	0.0244 (7)	0.0017 (5)	0.0007 (5)	−0.0013 (5)
C17	0.0368 (8)	0.0246 (7)	0.0401 (9)	−0.0019 (6)	0.0057 (7)	0.0036 (6)
C18	0.0476 (9)	0.0275 (8)	0.0275 (8)	0.0046 (7)	−0.0013 (7)	−0.0063 (6)
C19	0.0253 (7)	0.0275 (8)	0.0428 (9)	−0.0029 (6)	−0.0048 (6)	−0.0058 (6)

Geometric parameters (Å, º)

O1—C5	1.4237 (16)	C9—H9A	0.9700
O1—C6	1.4239 (16)	C9—H9B	0.9700
O2—C10	1.4211 (17)	C10—C11	1.5027 (18)
O2—C9	1.4259 (17)	C10—H10A	0.9700
N1—C1	1.3407 (15)	C10—H10B	0.9700
N1—C3	1.3484 (15)	C11—H11A	0.9700
N2—C1	1.3360 (15)	C11—H11B	0.9700
N2—C2	1.3430 (15)	C12—C13	1.5243 (17)
N3—C3	1.3366 (15)	C12—C14	1.5287 (18)
N3—C2	1.3487 (15)	C12—C15	1.5508 (17)
N4—C1	1.3641 (15)	C13—H13A	0.9600
N4—C4	1.4569 (15)	C13—H13B	0.9600
N4—C7	1.4596 (16)	C13—H13C	0.9600
N5—C3	1.3580 (16)	C14—H14A	0.9600
N5—C8	1.4541 (16)	C14—H14B	0.9600
N5—C11	1.4577 (16)	C14—H14C	0.9600
N6—C2	1.3496 (15)	C15—C16	1.5507 (18)
N6—C12	1.4818 (15)	C15—H15A	0.9700
N6—H6C	0.885 (8)	C15—H15B	0.9700
C4—C5	1.5039 (18)	C16—C19	1.5295 (18)
C4—H4A	0.9700	C16—C18	1.5311 (18)
C4—H4B	0.9700	C16—C17	1.5318 (18)
C5—H5A	0.9700	C17—H17A	0.9600
C5—H5B	0.9700	C17—H17B	0.9600
C6—C7	1.5138 (18)	C17—H17C	0.9600
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—H19A	0.9600
C8—C9	1.506 (2)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C8—H8B	0.9700
C5—O1—C6	109.97 (9)	O2—C10—H10A	109.2
C10—O2—C9	110.15 (10)	C11—C10—H10A	109.2
C1—N1—C3	113.63 (10)	O2—C10—H10B	109.2
C1—N2—C2	113.95 (10)	C11—C10—H10B	109.2
C3—N3—C2	114.07 (10)	H10A—C10—H10B	107.9
C1—N4—C4	120.55 (10)	N5—C11—C10	109.74 (11)
C1—N4—C7	121.50 (10)	N5—C11—H11A	109.7
C4—N4—C7	113.71 (10)	C10—C11—H11A	109.7
C3—N5—C8	123.48 (10)	N5—C11—H11B	109.7
C3—N5—C11	122.71 (10)	C10—C11—H11B	109.7
C8—N5—C11	113.74 (10)	H11A—C11—H11B	108.2
C2—N6—C12	127.71 (10)	N6—C12—C13	105.85 (10)
C2—N6—H6C	112.8 (8)	N6—C12—C14	108.64 (10)
C12—N6—H6C	119.0 (8)	C13—C12—C14	108.58 (10)
N2—C1—N1	126.51 (11)	N6—C12—C15	113.14 (9)
N2—C1—N4	116.99 (10)	C13—C12—C15	113.04 (10)
N1—C1—N4	116.47 (10)	C14—C12—C15	107.45 (10)
N2—C2—N3	125.73 (10)	C12—C13—H13A	109.5
N2—C2—N6	118.76 (10)	C12—C13—H13B	109.5
N3—C2—N6	115.50 (10)	H13A—C13—H13B	109.5
N3—C3—N1	126.02 (11)	C12—C13—H13C	109.5
N3—C3—N5	117.71 (11)	H13A—C13—H13C	109.5
N1—C3—N5	116.27 (10)	H13B—C13—H13C	109.5
N4—C4—C5	109.77 (11)	C12—C14—H14A	109.5
N4—C4—H4A	109.7	C12—C14—H14B	109.5
C5—C4—H4A	109.7	H14A—C14—H14B	109.5
N4—C4—H4B	109.7	C12—C14—H14C	109.5
C5—C4—H4B	109.7	H14A—C14—H14C	109.5
H4A—C4—H4B	108.2	H14B—C14—H14C	109.5
O1—C5—C4	111.79 (10)	C16—C15—C12	123.32 (10)
O1—C5—H5A	109.3	C16—C15—H15A	106.5
C4—C5—H5A	109.3	C12—C15—H15A	106.5
O1—C5—H5B	109.3	C16—C15—H15B	106.5
C4—C5—H5B	109.3	C12—C15—H15B	106.5
H5A—C5—H5B	107.9	H15A—C15—H15B	106.5
O1—C6—C7	112.15 (11)	C19—C16—C18	109.50 (11)
O1—C6—H6A	109.2	C19—C16—C17	108.06 (11)
C7—C6—H6A	109.2	C18—C16—C17	107.49 (11)
O1—C6—H6B	109.2	C19—C16—C15	113.57 (10)
C7—C6—H6B	109.2	C18—C16—C15	111.62 (11)
H6A—C6—H6B	107.9	C17—C16—C15	106.32 (11)
N4—C7—C6	109.13 (10)	C16—C17—H17A	109.5
N4—C7—H7A	109.9	C16—C17—H17B	109.5
C6—C7—H7A	109.9	H17A—C17—H17B	109.5
N4—C7—H7B	109.9	C16—C17—H17C	109.5
C6—C7—H7B	109.9	H17A—C17—H17C	109.5
H7A—C7—H7B	108.3	H17B—C17—H17C	109.5
N5—C8—C9	109.31 (12)	C16—C18—H18A	109.5
N5—C8—H8A	109.8	C16—C18—H18B	109.5
C9—C8—H8A	109.8	H18A—C18—H18B	109.5
N5—C8—H8B	109.8	C16—C18—H18C	109.5
C9—C8—H8B	109.8	H18A—C18—H18C	109.5
H8A—C8—H8B	108.3	H18B—C18—H18C	109.5
O2—C9—C8	111.24 (11)	C16—C19—H19A	109.5
O2—C9—H9A	109.4	C16—C19—H19B	109.5
C8—C9—H9A	109.4	H19A—C19—H19B	109.5
O2—C9—H9B	109.4	C16—C19—H19C	109.5
C8—C9—H9B	109.4	H19A—C19—H19C	109.5
H9A—C9—H9B	108.0	H19B—C19—H19C	109.5
O2—C10—C11	111.91 (11)
C2—N2—C1—N1	−3.13 (17)	C6—O1—C5—C4	59.52 (14)
C2—N2—C1—N4	178.72 (10)	N4—C4—C5—O1	−55.56 (14)
C3—N1—C1—N2	2.64 (16)	C5—O1—C6—C7	−59.49 (14)
C3—N1—C1—N4	−179.21 (10)	C1—N4—C7—C6	150.99 (11)
C4—N4—C1—N2	−163.16 (10)	C4—N4—C7—C6	−52.03 (14)
C7—N4—C1—N2	−7.73 (16)	O1—C6—C7—N4	55.05 (14)
C4—N4—C1—N1	18.50 (16)	C3—N5—C8—C9	−124.15 (13)
C7—N4—C1—N1	173.93 (10)	C11—N5—C8—C9	52.85 (15)
C1—N2—C2—N3	0.82 (16)	C10—O2—C9—C8	60.37 (15)
C1—N2—C2—N6	−177.92 (10)	N5—C8—C9—O2	−56.35 (15)
C3—N3—C2—N2	1.58 (16)	C9—O2—C10—C11	−59.46 (15)
C3—N3—C2—N6	−179.64 (10)	C3—N5—C11—C10	125.17 (13)
C12—N6—C2—N2	−9.04 (17)	C8—N5—C11—C10	−51.86 (15)
C12—N6—C2—N3	172.09 (10)	O2—C10—C11—N5	54.40 (14)
C2—N3—C3—N1	−2.16 (16)	C2—N6—C12—C13	−177.64 (11)
C2—N3—C3—N5	178.14 (10)	C2—N6—C12—C14	−61.20 (15)
C1—N1—C3—N3	0.26 (16)	C2—N6—C12—C15	58.04 (15)
C1—N1—C3—N5	179.96 (10)	N6—C12—C15—C16	63.93 (15)
C8—N5—C3—N3	175.78 (11)	C13—C12—C15—C16	−56.37 (15)
C11—N5—C3—N3	−0.96 (17)	C14—C12—C15—C16	−176.15 (11)
C8—N5—C3—N1	−3.95 (17)	C12—C15—C16—C19	−37.84 (16)
C11—N5—C3—N1	179.31 (11)	C12—C15—C16—C18	86.53 (14)
C1—N4—C4—C5	−150.20 (11)	C12—C15—C16—C17	−156.54 (11)
C7—N4—C4—C5	52.59 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6C···N1^i	0.89 (1)	2.39 (1)	3.2715 (15)	172 (1)

Symmetry code: (i) x, −y+1/2, z−1/2.