Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043462/sj2350sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043462/sj2350Isup2.hkl |
CCDC reference: 664198
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).
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, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
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.
For the preparation and uses of the title compound and similar compounds, see: Borzatta & Carrozza (1991); Deng et al. (2006); Kaiser & Thurston (1951).
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).
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. |
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) Å3 | Block, colorless |
Z = 4 | 0.08 × 0.08 × 0.02 mm |
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 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.0832P] where P = (Fo2 + 2Fc2)/3 |
3641 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
C19H34N6O2 | V = 2066.6 (7) Å3 |
Mr = 378.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.247 (2) Å | µ = 0.08 mm−1 |
b = 16.718 (3) Å | T = 113 K |
c = 12.107 (2) Å | 0.08 × 0.08 × 0.02 mm |
β = 94.82 (3)° |
Rigaku Saturn CCD diffractometer | 3641 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 3159 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.998 | Rint = 0.034 |
20763 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.20 e Å−3 |
3641 reflections | Δρmin = −0.27 e Å−3 |
253 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6C···N1i | 0.89 (1) | 2.39 (1) | 3.2715 (15) | 172 (1) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H34N6O2 |
Mr | 378.52 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 10.247 (2), 16.718 (3), 12.107 (2) |
β (°) | 94.82 (3) |
V (Å3) | 2066.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.08 × 0.08 × 0.02 |
Data collection | |
Diffractometer | Rigaku Saturn CCD |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.984, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20763, 3641, 3159 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.103, 1.09 |
No. of reflections | 3641 |
No. of parameters | 253 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.27 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6C···N1i | 0.885 (8) | 2.392 (9) | 3.2715 (15) | 172.4 (11) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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.