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The crystal structure of three derivatives of 2,4-dimethoxy-1,3,5-triazine are described. In 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)morpholine, C
9H
14N
4O
3, the morpholine moiety adopts a chair conformation, and the dimethoxytriazine molecule adopts a butterfly conformation with respect to the two methoxy groups. In 3-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)-2-methylphenol, C
12H
13N
3O
4, the dimethoxytriazine moiety adopts a propeller conformation with respect to the methoxy groups, and the molecules form dimers held together by O—H
N hydrogen bonds. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yloxy)phenyl phenyl ketone, C
18H
15N
3O
4, crystallizes with two crystallographically independent molecules in the asymmetric unit. The two molecules adopt different conformations with respect to the geometric relations between the phenyl ketone and triazine moieties.
Supporting information
CCDC references: 229102; 229103; 229104
Compound (I) was prepared according to the procedure described by Kunishima et al. (1999). Crystals were grown from methanol solution.
For the preparation of compound (II), a solution (10 mmol) of sodium hydroxide (0.2 g, 5 mmol) in methanol was heated to 313 K. A solution of 1,3,5-triazine 2,2'-[2-methyl-1,3-phenilenebis(oxy)] bis[4,6-dichloro]-(9CI) (0.84 g, 2 mmol) in tetrahydrofuran (10 ml) was added and the resulting mixture was refluxed at 353 K for 1.5 h. The mixture was diluted with water (20 ml), and the solution was treated with ether (15 ml) in order to extract the product. The solution was dried over MgSO4 and the resulting mixture was allowed to stand for 2 h. The ether extract was filtered and concentrated to dryness in vacuo and the product was obtained in 96% yield. Crystals suitable for X-ray diffraction were grown from a solution (1:1) of ethyl acetate and methanol.
Compound (III) was prepared according to the procedure described by Yonehara et al. (1994). Crystals suitable for X-ray diffraction were grown from a mixture (1:1) of methanol and methylene chloride.
In all three structures, H atoms were located from difference Fourier maps. During refinement, the position of the hydroxy H atom in (II) was refined refined freely? All other H atoms were constrained to ride on their parent atoms.
For all compounds, data collection: Collect (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for (I), (III); ORTEP-3 for Windows for (II).
(I) 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)morpholine
top
Crystal data top
C9H14N4O3 | F(000) = 480 |
Mr = 226.24 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2944 reflections |
a = 10.244 (2) Å | θ = 2.5–25.0° |
b = 9.208 (3) Å | µ = 0.11 mm−1 |
c = 11.615 (3) Å | T = 293 K |
β = 99.70 (3)° | Needle, colorless |
V = 1079.9 (5) Å3 | 0.33 × 0.15 × 0.12 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 883 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
Detector resolution: 95 pixels mm-1 | h = −12→11 |
ϕ scan | k = −9→10 |
2944 measured reflections | l = −13→13 |
1799 independent reflections | |
Refinement top
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3 |
1799 reflections | (Δ/σ)max = 0.001 |
147 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Crystal data top
C9H14N4O3 | V = 1079.9 (5) Å3 |
Mr = 226.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.244 (2) Å | µ = 0.11 mm−1 |
b = 9.208 (3) Å | T = 293 K |
c = 11.615 (3) Å | 0.33 × 0.15 × 0.12 mm |
β = 99.70 (3)° | |
Data collection top
Nonius KappaCCD diffractometer | 883 reflections with I > 2σ(I) |
2944 measured reflections | Rint = 0.060 |
1799 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.16 e Å−3 |
1799 reflections | Δρmin = −0.15 e Å−3 |
147 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4894 (3) | 0.3130 (3) | 1.0732 (2) | 0.0761 (8) | |
O2 | 0.1476 (2) | 0.0214 (3) | 0.9495 (2) | 0.0776 (8) | |
O3 | 0.6562 (3) | −0.1168 (3) | 0.6140 (2) | 0.0807 (8) | |
N1 | 0.3170 (3) | 0.0206 (3) | 0.8453 (2) | 0.0611 (8) | |
N2 | 0.4992 (3) | 0.1777 (3) | 0.9100 (2) | 0.0601 (8) | |
N3 | 0.3162 (3) | 0.1699 (3) | 1.0113 (2) | 0.0681 (9) | |
N4 | 0.4961 (3) | 0.0335 (3) | 0.7474 (2) | 0.0667 (8) | |
C1 | 0.4359 (3) | 0.0791 (4) | 0.8364 (3) | 0.0568 (9) | |
C2 | 0.4338 (4) | 0.2165 (4) | 0.9932 (3) | 0.0621 (9) | |
C3 | 0.2658 (4) | 0.0720 (4) | 0.9335 (3) | 0.0629 (10) | |
C4 | 0.6208 (4) | 0.3638 (4) | 1.0645 (3) | 0.0857 (12) | |
H4A | 0.6497 | 0.4319 | 1.1261 | 0.129* | |
H4B | 0.6193 | 0.4104 | 0.9903 | 0.129* | |
H4C | 0.6807 | 0.2829 | 1.0712 | 0.129* | |
C5 | 0.0796 (4) | −0.0807 (5) | 0.8682 (3) | 0.0871 (13) | |
H5A | 0.0712 | −0.0420 | 0.7906 | 0.131* | |
H5B | −0.0068 | −0.0988 | 0.8866 | 0.131* | |
H5C | 0.1287 | −0.1699 | 0.8728 | 0.131* | |
C6 | 0.6208 (3) | 0.0957 (4) | 0.7259 (3) | 0.0740 (11) | |
H6A | 0.6606 | 0.1526 | 0.7930 | 0.089* | |
H6B | 0.6041 | 0.1598 | 0.6587 | 0.089* | |
C7 | 0.7139 (4) | −0.0214 (4) | 0.7039 (3) | 0.0771 (11) | |
H7A | 0.7927 | 0.0220 | 0.6825 | 0.093* | |
H7B | 0.7406 | −0.0765 | 0.7752 | 0.093* | |
C8 | 0.5426 (4) | −0.1824 (4) | 0.6453 (3) | 0.0822 (12) | |
H8A | 0.5681 | −0.2365 | 0.7172 | 0.099* | |
H8B | 0.5056 | −0.2505 | 0.5848 | 0.099* | |
C9 | 0.4393 (4) | −0.0734 (4) | 0.6617 (3) | 0.0752 (11) | |
H9A | 0.4064 | −0.0258 | 0.5880 | 0.090* | |
H9B | 0.3656 | −0.1217 | 0.6882 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0883 (19) | 0.0788 (18) | 0.0638 (16) | −0.0046 (14) | 0.0202 (14) | −0.0111 (15) |
O2 | 0.0632 (16) | 0.097 (2) | 0.0775 (17) | −0.0019 (14) | 0.0263 (13) | −0.0008 (15) |
O3 | 0.0886 (19) | 0.0840 (18) | 0.0756 (18) | −0.0007 (15) | 0.0311 (14) | −0.0152 (15) |
N1 | 0.0547 (18) | 0.0708 (19) | 0.0594 (18) | 0.0018 (15) | 0.0144 (14) | 0.0025 (15) |
N2 | 0.0646 (18) | 0.0626 (19) | 0.0546 (18) | 0.0038 (15) | 0.0141 (15) | −0.0044 (15) |
N3 | 0.073 (2) | 0.077 (2) | 0.058 (2) | 0.0016 (17) | 0.0213 (16) | −0.0011 (17) |
N4 | 0.0604 (19) | 0.076 (2) | 0.0684 (19) | −0.0083 (15) | 0.0234 (15) | −0.0144 (16) |
C1 | 0.060 (2) | 0.059 (2) | 0.053 (2) | 0.0116 (18) | 0.0157 (17) | 0.0033 (18) |
C2 | 0.072 (3) | 0.064 (2) | 0.053 (2) | 0.0084 (19) | 0.016 (2) | 0.0043 (19) |
C3 | 0.058 (2) | 0.075 (3) | 0.059 (2) | 0.0063 (19) | 0.0177 (19) | 0.007 (2) |
C4 | 0.080 (3) | 0.090 (3) | 0.086 (3) | −0.014 (2) | 0.011 (2) | −0.015 (2) |
C5 | 0.070 (3) | 0.103 (3) | 0.090 (3) | −0.017 (2) | 0.020 (2) | −0.009 (3) |
C6 | 0.072 (3) | 0.080 (3) | 0.075 (3) | −0.005 (2) | 0.027 (2) | −0.010 (2) |
C7 | 0.071 (2) | 0.095 (3) | 0.069 (2) | 0.004 (2) | 0.0237 (19) | −0.001 (2) |
C8 | 0.096 (3) | 0.077 (3) | 0.080 (3) | −0.006 (2) | 0.035 (2) | −0.017 (2) |
C9 | 0.074 (3) | 0.090 (3) | 0.064 (2) | −0.016 (2) | 0.0201 (19) | −0.013 (2) |
Geometric parameters (Å, º) top
O1—C2 | 1.342 (4) | C4—H4B | 0.9600 |
O1—C4 | 1.445 (4) | C4—H4C | 0.9600 |
O2—C3 | 1.339 (4) | C5—H5A | 0.9600 |
O2—C5 | 1.428 (4) | C5—H5B | 0.9600 |
O3—C8 | 1.412 (4) | C5—H5C | 0.9600 |
O3—C7 | 1.415 (4) | C6—C7 | 1.490 (5) |
N1—C3 | 1.315 (4) | C6—H6A | 0.9700 |
N1—C1 | 1.352 (4) | C6—H6B | 0.9700 |
N2—C2 | 1.314 (4) | C7—H7A | 0.9700 |
N2—C1 | 1.338 (4) | C7—H7B | 0.9700 |
N3—C3 | 1.318 (4) | C8—C9 | 1.494 (5) |
N3—C2 | 1.328 (4) | C8—H8A | 0.9700 |
N4—C1 | 1.357 (4) | C8—H8B | 0.9700 |
N4—C9 | 1.450 (4) | C9—H9A | 0.9700 |
N4—C6 | 1.459 (4) | C9—H9B | 0.9700 |
C4—H4A | 0.9600 | | |
| | | |
C2—O1—C4 | 117.2 (3) | O2—C5—H5C | 109.5 |
C3—O2—C5 | 119.3 (3) | H5A—C5—H5C | 109.5 |
C8—O3—C7 | 109.6 (3) | H5B—C5—H5C | 109.5 |
C3—N1—C1 | 113.6 (3) | N4—C6—C7 | 110.4 (3) |
C2—N2—C1 | 113.7 (3) | N4—C6—H6A | 109.6 |
C3—N3—C2 | 112.0 (3) | C7—C6—H6A | 109.6 |
C1—N4—C9 | 123.4 (3) | N4—C6—H6B | 109.6 |
C1—N4—C6 | 122.2 (3) | C7—C6—H6B | 109.6 |
C9—N4—C6 | 114.3 (3) | H6A—C6—H6B | 108.1 |
N2—C1—N1 | 124.5 (3) | O3—C7—C6 | 112.1 (3) |
N2—C1—N4 | 117.6 (3) | O3—C7—H7A | 109.2 |
N1—C1—N4 | 117.8 (3) | C6—C7—H7A | 109.2 |
N2—C2—N3 | 128.0 (3) | O3—C7—H7B | 109.2 |
N2—C2—O1 | 118.7 (3) | C6—C7—H7B | 109.2 |
N3—C2—O1 | 113.3 (3) | H7A—C7—H7B | 107.9 |
N1—C3—N3 | 128.1 (4) | O3—C8—C9 | 112.2 (3) |
N1—C3—O2 | 118.1 (3) | O3—C8—H8A | 109.2 |
N3—C3—O2 | 113.7 (3) | C9—C8—H8A | 109.2 |
O1—C4—H4A | 109.5 | O3—C8—H8B | 109.2 |
O1—C4—H4B | 109.5 | C9—C8—H8B | 109.2 |
H4A—C4—H4B | 109.5 | H8A—C8—H8B | 107.9 |
O1—C4—H4C | 109.5 | N4—C9—C8 | 109.4 (3) |
H4A—C4—H4C | 109.5 | N4—C9—H9A | 109.8 |
H4B—C4—H4C | 109.5 | C8—C9—H9A | 109.8 |
O2—C5—H5A | 109.5 | N4—C9—H9B | 109.8 |
O2—C5—H5B | 109.5 | C8—C9—H9B | 109.8 |
H5A—C5—H5B | 109.5 | H9A—C9—H9B | 108.2 |
| | | |
C2—N2—C1—N1 | −1.1 (5) | C1—N1—C3—N3 | −0.4 (5) |
C2—N2—C1—N4 | 179.6 (3) | C1—N1—C3—O2 | 179.7 (3) |
C3—N1—C1—N2 | 1.3 (4) | C2—N3—C3—N1 | −0.6 (5) |
C3—N1—C1—N4 | −179.5 (3) | C2—N3—C3—O2 | 179.4 (3) |
C9—N4—C1—N2 | 179.6 (3) | C5—O2—C3—N1 | −2.7 (5) |
C6—N4—C1—N2 | −4.3 (5) | C5—O2—C3—N3 | 177.3 (3) |
C9—N4—C1—N1 | 0.3 (5) | C1—N4—C6—C7 | 134.4 (3) |
C6—N4—C1—N1 | 176.4 (3) | C9—N4—C6—C7 | −49.2 (4) |
C1—N2—C2—N3 | 0.1 (5) | C8—O3—C7—C6 | −59.8 (4) |
C1—N2—C2—O1 | 178.8 (3) | N4—C6—C7—O3 | 53.5 (4) |
C3—N3—C2—N2 | 0.7 (5) | C7—O3—C8—C9 | 61.2 (4) |
C3—N3—C2—O1 | −178.1 (3) | C1—N4—C9—C8 | −133.8 (3) |
C4—O1—C2—N2 | −2.3 (4) | C6—N4—C9—C8 | 49.8 (4) |
C4—O1—C2—N3 | 176.7 (3) | O3—C8—C9—N4 | −55.7 (4) |
(II) 3-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)-2-methylphenol
top
Crystal data top
C12H13N3O4 | Z = 2 |
Mr = 263.25 | F(000) = 276 |
Triclinic, P1 | Dx = 1.409 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.386 (2) Å | Cell parameters from 2195 reflections |
b = 9.718 (2) Å | θ = 2.2–25.1° |
c = 9.868 (2) Å | µ = 0.11 mm−1 |
α = 108.73 (2)° | T = 293 K |
β = 93.36 (2)° | Plate, colorless |
γ = 109.67 (2)° | 0.45 × 0.30 × 0.12 mm |
V = 620.5 (3) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 1496 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.1°, θmin = 2.2° |
Detector resolution: 95 pixels mm-1 | h = 0→8 |
ϕ scan | k = −11→10 |
2195 measured reflections | l = −11→11 |
2195 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0796P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.033 |
2195 reflections | Δρmax = 0.20 e Å−3 |
180 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.147 (19) |
Crystal data top
C12H13N3O4 | γ = 109.67 (2)° |
Mr = 263.25 | V = 620.5 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.386 (2) Å | Mo Kα radiation |
b = 9.718 (2) Å | µ = 0.11 mm−1 |
c = 9.868 (2) Å | T = 293 K |
α = 108.73 (2)° | 0.45 × 0.30 × 0.12 mm |
β = 93.36 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 1496 reflections with I > 2σ(I) |
2195 measured reflections | Rint = 0.000 |
2195 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2195 reflections | Δρmin = −0.18 e Å−3 |
180 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2006 (2) | −0.08654 (16) | 0.23330 (15) | 0.0598 (4) | |
O2 | 0.2673 (2) | −0.04644 (16) | 0.70501 (15) | 0.0591 (4) | |
O3 | 0.28057 (19) | 0.36964 (15) | 0.58597 (13) | 0.0521 (4) | |
O4 | 0.72997 (19) | 0.73066 (18) | 1.02197 (16) | 0.0578 (4) | |
N1 | 0.2749 (2) | 0.16300 (18) | 0.65529 (16) | 0.0446 (4) | |
N2 | 0.2402 (2) | 0.14724 (18) | 0.40902 (16) | 0.0463 (4) | |
N3 | 0.2328 (2) | −0.07614 (18) | 0.46333 (17) | 0.0500 (4) | |
C1 | 0.2652 (3) | 0.2205 (2) | 0.5521 (2) | 0.0418 (5) | |
C2 | 0.2258 (3) | 0.0002 (2) | 0.3730 (2) | 0.0449 (5) | |
C3 | 0.2571 (3) | 0.0128 (2) | 0.60157 (19) | 0.0444 (5) | |
C4 | 0.1937 (4) | −0.0120 (3) | 0.1293 (2) | 0.0690 (7) | |
H4A | 0.0963 | 0.0337 | 0.1441 | 0.104* | |
H4B | 0.1610 | −0.0885 | 0.0324 | 0.104* | |
H4C | 0.3192 | 0.0685 | 0.1422 | 0.104* | |
C5 | 0.2366 (4) | −0.2092 (3) | 0.6605 (3) | 0.0719 (7) | |
H5A | 0.1079 | −0.2710 | 0.6028 | 0.108* | |
H5B | 0.2489 | −0.2363 | 0.7450 | 0.108* | |
H5C | 0.3324 | −0.2294 | 0.6039 | 0.108* | |
C6 | 0.3184 (3) | 0.4681 (2) | 0.73407 (19) | 0.0423 (5) | |
C7 | 0.5118 (2) | 0.5495 (2) | 0.80501 (19) | 0.0419 (5) | |
C8 | 0.5417 (3) | 0.6530 (2) | 0.9474 (2) | 0.0426 (5) | |
C9 | 0.3870 (3) | 0.6779 (2) | 1.0098 (2) | 0.0467 (5) | |
H9 | 0.4108 | 0.7508 | 1.1035 | 0.056* | |
C10 | 0.1982 (3) | 0.5954 (2) | 0.9335 (2) | 0.0514 (5) | |
H10 | 0.0948 | 0.6124 | 0.9761 | 0.062* | |
C11 | 0.1615 (3) | 0.4874 (2) | 0.7938 (2) | 0.0490 (5) | |
H11 | 0.0342 | 0.4295 | 0.7419 | 0.059* | |
C12 | 0.6781 (3) | 0.5253 (3) | 0.7340 (2) | 0.0573 (6) | |
H12A | 0.6837 | 0.4272 | 0.7311 | 0.086* | |
H12B | 0.7987 | 0.6091 | 0.7888 | 0.086* | |
H12C | 0.6584 | 0.5242 | 0.6366 | 0.086* | |
H4O | 0.735 (4) | 0.776 (4) | 1.130 (3) | 0.123 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0887 (10) | 0.0468 (9) | 0.0414 (8) | 0.0281 (8) | 0.0120 (7) | 0.0100 (7) |
O2 | 0.0826 (10) | 0.0461 (9) | 0.0488 (9) | 0.0226 (7) | 0.0032 (7) | 0.0207 (7) |
O3 | 0.0782 (10) | 0.0390 (8) | 0.0397 (8) | 0.0266 (7) | 0.0040 (6) | 0.0115 (6) |
O4 | 0.0526 (8) | 0.0585 (10) | 0.0495 (9) | 0.0115 (7) | 0.0010 (6) | 0.0147 (7) |
N1 | 0.0533 (9) | 0.0381 (9) | 0.0405 (9) | 0.0173 (7) | 0.0039 (7) | 0.0127 (7) |
N2 | 0.0585 (10) | 0.0396 (10) | 0.0378 (9) | 0.0186 (8) | 0.0044 (7) | 0.0110 (7) |
N3 | 0.0615 (10) | 0.0401 (10) | 0.0469 (10) | 0.0192 (8) | 0.0070 (8) | 0.0144 (8) |
C1 | 0.0456 (10) | 0.0355 (11) | 0.0410 (11) | 0.0152 (8) | 0.0034 (8) | 0.0105 (9) |
C2 | 0.0491 (11) | 0.0398 (12) | 0.0414 (11) | 0.0154 (9) | 0.0080 (8) | 0.0104 (9) |
C3 | 0.0476 (10) | 0.0408 (12) | 0.0440 (12) | 0.0157 (9) | 0.0052 (8) | 0.0159 (10) |
C4 | 0.1035 (17) | 0.0594 (15) | 0.0401 (12) | 0.0293 (13) | 0.0088 (11) | 0.0151 (11) |
C5 | 0.0972 (17) | 0.0465 (14) | 0.0769 (17) | 0.0243 (12) | 0.0096 (13) | 0.0327 (13) |
C6 | 0.0592 (12) | 0.0329 (10) | 0.0363 (10) | 0.0196 (9) | 0.0055 (8) | 0.0127 (8) |
C7 | 0.0510 (11) | 0.0392 (11) | 0.0431 (11) | 0.0210 (9) | 0.0121 (8) | 0.0196 (9) |
C8 | 0.0508 (11) | 0.0357 (11) | 0.0425 (11) | 0.0136 (9) | 0.0067 (8) | 0.0188 (9) |
C9 | 0.0633 (12) | 0.0397 (11) | 0.0399 (11) | 0.0220 (10) | 0.0149 (9) | 0.0142 (9) |
C10 | 0.0558 (12) | 0.0494 (12) | 0.0609 (13) | 0.0263 (10) | 0.0228 (10) | 0.0261 (11) |
C11 | 0.0474 (11) | 0.0412 (11) | 0.0572 (13) | 0.0162 (9) | 0.0067 (9) | 0.0174 (10) |
C12 | 0.0610 (13) | 0.0651 (15) | 0.0544 (13) | 0.0302 (11) | 0.0211 (10) | 0.0240 (11) |
Geometric parameters (Å, º) top
O1—C2 | 1.328 (2) | C5—H5A | 0.9600 |
O1—C4 | 1.441 (3) | C5—H5B | 0.9600 |
O2—C3 | 1.333 (2) | C5—H5C | 0.9600 |
O2—C5 | 1.430 (2) | C6—C11 | 1.371 (3) |
O3—C1 | 1.341 (2) | C6—C7 | 1.386 (3) |
O3—C6 | 1.416 (2) | C7—C8 | 1.394 (3) |
O4—C8 | 1.364 (2) | C7—C12 | 1.498 (2) |
O4—H4O | 1.01 (3) | C8—C9 | 1.384 (3) |
N1—C1 | 1.319 (2) | C9—C10 | 1.375 (3) |
N1—C3 | 1.339 (2) | C9—H9 | 0.9300 |
N2—C2 | 1.322 (2) | C10—C11 | 1.382 (3) |
N2—C1 | 1.330 (2) | C10—H10 | 0.9300 |
N3—C3 | 1.323 (2) | C11—H11 | 0.9300 |
N3—C2 | 1.339 (2) | C12—H12A | 0.9600 |
C4—H4A | 0.9600 | C12—H12B | 0.9600 |
C4—H4B | 0.9600 | C12—H12C | 0.9600 |
C4—H4C | 0.9600 | | |
| | | |
C2—O1—C4 | 117.11 (16) | H5A—C5—H5C | 109.5 |
C3—O2—C5 | 117.97 (16) | H5B—C5—H5C | 109.5 |
C1—O3—C6 | 119.56 (14) | C11—C6—C7 | 124.23 (17) |
C8—O4—H4O | 111.3 (18) | C11—C6—O3 | 117.40 (16) |
C1—N1—C3 | 112.28 (16) | C7—C6—O3 | 118.09 (15) |
C2—N2—C1 | 112.88 (16) | C6—C7—C8 | 115.86 (15) |
C3—N3—C2 | 112.52 (16) | C6—C7—C12 | 122.09 (17) |
N1—C1—N2 | 127.73 (17) | C8—C7—C12 | 122.04 (17) |
N1—C1—O3 | 120.50 (16) | O4—C8—C9 | 121.42 (17) |
N2—C1—O3 | 111.77 (16) | O4—C8—C7 | 117.26 (16) |
N2—C2—O1 | 119.10 (17) | C9—C8—C7 | 121.31 (17) |
N2—C2—N3 | 127.05 (17) | C10—C9—C8 | 120.25 (17) |
O1—C2—N3 | 113.85 (16) | C10—C9—H9 | 119.9 |
N3—C3—O2 | 119.68 (17) | C8—C9—H9 | 119.9 |
N3—C3—N1 | 127.53 (17) | C9—C10—C11 | 120.28 (17) |
O2—C3—N1 | 112.79 (16) | C9—C10—H10 | 119.9 |
O1—C4—H4A | 109.5 | C11—C10—H10 | 119.9 |
O1—C4—H4B | 109.5 | C6—C11—C10 | 117.99 (18) |
H4A—C4—H4B | 109.5 | C6—C11—H11 | 121.0 |
O1—C4—H4C | 109.5 | C10—C11—H11 | 121.0 |
H4A—C4—H4C | 109.5 | C7—C12—H12A | 109.5 |
H4B—C4—H4C | 109.5 | C7—C12—H12B | 109.5 |
O2—C5—H5A | 109.5 | H12A—C12—H12B | 109.5 |
O2—C5—H5B | 109.5 | C7—C12—H12C | 109.5 |
H5A—C5—H5B | 109.5 | H12A—C12—H12C | 109.5 |
O2—C5—H5C | 109.5 | H12B—C12—H12C | 109.5 |
| | | |
C3—N1—C1—N2 | 0.2 (3) | C1—N1—C3—O2 | 179.81 (14) |
C3—N1—C1—O3 | −179.89 (15) | C1—O3—C6—C11 | −98.15 (19) |
C2—N2—C1—N1 | −0.5 (3) | C1—O3—C6—C7 | 87.6 (2) |
C2—N2—C1—O3 | 179.60 (15) | C11—C6—C7—C8 | 1.9 (3) |
C6—O3—C1—N1 | 3.5 (2) | O3—C6—C7—C8 | 175.69 (14) |
C6—O3—C1—N2 | −176.60 (14) | C11—C6—C7—C12 | −179.25 (18) |
C1—N2—C2—O1 | −179.97 (16) | O3—C6—C7—C12 | −5.4 (2) |
C1—N2—C2—N3 | 0.4 (3) | C6—C7—C8—O4 | 177.71 (15) |
C4—O1—C2—N2 | 1.0 (3) | C12—C7—C8—O4 | −1.2 (3) |
C4—O1—C2—N3 | −179.37 (16) | C6—C7—C8—C9 | −3.3 (3) |
C3—N3—C2—N2 | −0.1 (3) | C12—C7—C8—C9 | 177.78 (16) |
C3—N3—C2—O1 | −179.70 (15) | O4—C8—C9—C10 | −178.45 (16) |
C2—N3—C3—O2 | −179.85 (15) | C7—C8—C9—C10 | 2.6 (3) |
C2—N3—C3—N1 | −0.3 (3) | C8—C9—C10—C11 | −0.3 (3) |
C5—O2—C3—N3 | −4.6 (3) | C7—C6—C11—C10 | 0.4 (3) |
C5—O2—C3—N1 | 175.75 (17) | O3—C6—C11—C10 | −173.51 (16) |
C1—N1—C3—N3 | 0.2 (3) | C9—C10—C11—C6 | −1.2 (3) |
(III) 4-(4,6-Dimethoxy-1,3,5-triazin-2-yloxy)phenyl phenyl ketone
top
Crystal data top
C18H15N3O4 | F(000) = 2816 |
Mr = 337.33 | Dx = 1.351 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 11206 reflections |
a = 32.610 (6) Å | θ = 1.3–25.1° |
b = 13.757 (3) Å | µ = 0.10 mm−1 |
c = 15.904 (3) Å | T = 293 K |
β = 111.56 (2)° | Prism, colorless |
V = 6636 (2) Å3 | 0.60 × 0.30 × 0.27 mm |
Z = 16 | |
Data collection top
Nnius KappaCCD diffractometer | 3022 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.1°, θmin = 1.3° |
Detector resolution: 95 pixels mm-1 | h = −38→38 |
ϕ scan | k = −16→15 |
11206 measured reflections | l = −18→18 |
5860 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max = 0.001 |
5860 reflections | Δρmax = 0.17 e Å−3 |
456 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (3) |
Crystal data top
C18H15N3O4 | V = 6636 (2) Å3 |
Mr = 337.33 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.610 (6) Å | µ = 0.10 mm−1 |
b = 13.757 (3) Å | T = 293 K |
c = 15.904 (3) Å | 0.60 × 0.30 × 0.27 mm |
β = 111.56 (2)° | |
Data collection top
Nnius KappaCCD diffractometer | 3022 reflections with I > 2σ(I) |
11206 measured reflections | Rint = 0.028 |
5860 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.17 e Å−3 |
5860 reflections | Δρmin = −0.14 e Å−3 |
456 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.66170 (4) | −0.00892 (9) | 0.48751 (8) | 0.0622 (3) | |
O2A | 0.66417 (4) | −0.26587 (8) | 0.66506 (8) | 0.0688 (4) | |
O3A | 0.67589 (4) | 0.03023 (8) | 0.78378 (8) | 0.0617 (3) | |
O4A | 0.71875 (5) | 0.46717 (10) | 0.73537 (10) | 0.0909 (5) | |
N1A | 0.66961 (4) | −0.11831 (10) | 0.72511 (9) | 0.0555 (4) | |
N2A | 0.66797 (4) | 0.01990 (10) | 0.63372 (9) | 0.0515 (4) | |
N3A | 0.66272 (4) | −0.13890 (10) | 0.57137 (10) | 0.0558 (4) | |
C1A | 0.67122 (5) | −0.02454 (12) | 0.70984 (12) | 0.0510 (4) | |
C2A | 0.66422 (5) | −0.04273 (13) | 0.56765 (12) | 0.0516 (4) | |
C3A | 0.66528 (5) | −0.17101 (12) | 0.65149 (13) | 0.0548 (5) | |
C4A | 0.66598 (6) | 0.09463 (13) | 0.47840 (13) | 0.0704 (5) | |
H4A1 | 0.6680 | 0.1084 | 0.4209 | 0.106* | |
H4A2 | 0.6921 | 0.1174 | 0.5259 | 0.106* | |
H4A3 | 0.6407 | 0.1270 | 0.4824 | 0.106* | |
C5A | 0.66213 (8) | −0.32999 (14) | 0.59088 (14) | 0.0890 (7) | |
H5A1 | 0.6629 | −0.3964 | 0.6099 | 0.133* | |
H5A2 | 0.6869 | −0.3176 | 0.5735 | 0.133* | |
H5A3 | 0.6353 | −0.3183 | 0.5403 | 0.133* | |
C6A | 0.68543 (6) | 0.13006 (12) | 0.78587 (11) | 0.0522 (4) | |
C7A | 0.71676 (5) | 0.16633 (13) | 0.75524 (12) | 0.0569 (5) | |
H7A | 0.7322 | 0.1252 | 0.7310 | 0.068* | |
C8A | 0.72465 (5) | 0.26472 (13) | 0.76128 (12) | 0.0558 (5) | |
H8A | 0.7448 | 0.2905 | 0.7384 | 0.067* | |
C9A | 0.70326 (5) | 0.32649 (12) | 0.80074 (11) | 0.0515 (4) | |
C10A | 0.67356 (6) | 0.28721 (13) | 0.83508 (12) | 0.0594 (5) | |
H10A | 0.6599 | 0.3273 | 0.8640 | 0.071* | |
C11A | 0.66397 (6) | 0.18858 (13) | 0.82684 (12) | 0.0608 (5) | |
H11A | 0.6435 | 0.1625 | 0.8486 | 0.073* | |
C12A | 0.71147 (6) | 0.43276 (13) | 0.79954 (12) | 0.0590 (5) | |
C13A | 0.71174 (5) | 0.49715 (12) | 0.87423 (11) | 0.0509 (4) | |
C14A | 0.72609 (6) | 0.46591 (14) | 0.96302 (12) | 0.0616 (5) | |
H14A | 0.7337 | 0.4010 | 0.9766 | 0.074* | |
C15A | 0.72921 (6) | 0.53018 (17) | 1.03173 (13) | 0.0747 (6) | |
H15A | 0.7391 | 0.5086 | 1.0913 | 0.090* | |
C16A | 0.71780 (7) | 0.62593 (18) | 1.01218 (17) | 0.0830 (7) | |
H16A | 0.7199 | 0.6691 | 1.0586 | 0.100* | |
C17A | 0.70325 (7) | 0.65818 (15) | 0.92412 (17) | 0.0796 (6) | |
H17A | 0.6953 | 0.7229 | 0.9109 | 0.096* | |
C18A | 0.70051 (6) | 0.59436 (13) | 0.85565 (13) | 0.0634 (5) | |
H18A | 0.6910 | 0.6165 | 0.7963 | 0.076* | |
O1B | 0.55405 (5) | −0.13085 (12) | 0.68846 (11) | 0.0931 (5) | |
O2B | 0.55174 (4) | −0.07859 (11) | 0.40614 (10) | 0.0838 (4) | |
O3B | 0.56970 (4) | 0.17284 (11) | 0.60023 (9) | 0.0799 (4) | |
O4B | 0.60214 (7) | 0.55525 (13) | 0.41719 (12) | 0.1350 (7) | |
N1B | 0.56012 (5) | 0.04895 (12) | 0.49707 (11) | 0.0664 (4) | |
N2B | 0.56129 (5) | 0.02472 (13) | 0.64632 (11) | 0.0712 (5) | |
N3B | 0.55230 (5) | −0.11068 (12) | 0.54833 (13) | 0.0729 (5) | |
C1B | 0.56320 (6) | 0.07807 (15) | 0.57829 (15) | 0.0662 (5) | |
C2B | 0.55604 (6) | −0.06808 (17) | 0.62653 (15) | 0.0706 (6) | |
C3B | 0.55467 (6) | −0.04791 (17) | 0.48776 (14) | 0.0664 (5) | |
C4B | 0.56141 (9) | −0.0920 (2) | 0.77716 (16) | 0.1177 (9) | |
H4B1 | 0.5552 | −0.1413 | 0.8137 | 0.177* | |
H4B2 | 0.5423 | −0.0374 | 0.7718 | 0.177* | |
H4B3 | 0.5916 | −0.0717 | 0.8050 | 0.177* | |
C5B | 0.54694 (8) | −0.18171 (16) | 0.38823 (17) | 0.1075 (8) | |
H5B1 | 0.5463 | −0.1943 | 0.3284 | 0.161* | |
H5B2 | 0.5199 | −0.2039 | 0.3929 | 0.161* | |
H5B3 | 0.5714 | −0.2155 | 0.4315 | 0.161* | |
C6B | 0.57394 (6) | 0.24221 (14) | 0.53968 (13) | 0.0645 (5) | |
C7B | 0.61082 (6) | 0.30019 (16) | 0.57181 (14) | 0.0751 (6) | |
H7B | 0.6327 | 0.2876 | 0.6278 | 0.090* | |
C8B | 0.61496 (6) | 0.37705 (16) | 0.52025 (15) | 0.0769 (6) | |
H8B | 0.6391 | 0.4184 | 0.5428 | 0.092* | |
C9B | 0.58334 (6) | 0.39355 (14) | 0.43455 (13) | 0.0677 (5) | |
C10B | 0.54651 (6) | 0.33326 (14) | 0.40403 (13) | 0.0688 (5) | |
H10B | 0.5251 | 0.3436 | 0.3470 | 0.083* | |
C11B | 0.54131 (6) | 0.25847 (14) | 0.45697 (13) | 0.0676 (5) | |
H11B | 0.5162 | 0.2198 | 0.4370 | 0.081* | |
C12B | 0.58723 (7) | 0.47854 (16) | 0.38038 (16) | 0.0841 (6) | |
C13B | 0.57322 (7) | 0.46914 (17) | 0.28112 (16) | 0.0784 (6) | |
C14B | 0.57830 (6) | 0.38307 (19) | 0.24151 (15) | 0.0825 (6) | |
H14B | 0.5891 | 0.3286 | 0.2775 | 0.099* | |
C15B | 0.56759 (8) | 0.3766 (2) | 0.14892 (18) | 0.0994 (8) | |
H15B | 0.5718 | 0.3186 | 0.1231 | 0.119* | |
C16B | 0.55100 (9) | 0.4551 (3) | 0.0964 (2) | 0.1204 (11) | |
H16B | 0.5437 | 0.4509 | 0.0342 | 0.145* | |
C17B | 0.54477 (10) | 0.5411 (3) | 0.1340 (2) | 0.1269 (11) | |
H17B | 0.5327 | 0.5942 | 0.0970 | 0.152* | |
C18B | 0.55641 (8) | 0.5493 (2) | 0.2270 (2) | 0.1060 (8) | |
H18B | 0.5529 | 0.6081 | 0.2525 | 0.127* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0828 (8) | 0.0524 (8) | 0.0551 (8) | −0.0039 (6) | 0.0297 (6) | −0.0017 (6) |
O2A | 0.0955 (9) | 0.0385 (8) | 0.0681 (8) | −0.0054 (6) | 0.0248 (7) | −0.0048 (6) |
O3A | 0.0912 (9) | 0.0428 (8) | 0.0536 (7) | −0.0048 (6) | 0.0295 (6) | −0.0043 (6) |
O4A | 0.1656 (14) | 0.0581 (9) | 0.0744 (10) | −0.0166 (9) | 0.0741 (10) | −0.0043 (8) |
N1A | 0.0719 (9) | 0.0386 (9) | 0.0546 (9) | −0.0043 (7) | 0.0216 (7) | −0.0027 (7) |
N2A | 0.0623 (9) | 0.0423 (9) | 0.0485 (9) | −0.0012 (6) | 0.0186 (7) | −0.0012 (8) |
N3A | 0.0676 (9) | 0.0418 (10) | 0.0566 (10) | −0.0031 (7) | 0.0213 (7) | −0.0050 (7) |
C1A | 0.0559 (10) | 0.0461 (12) | 0.0494 (11) | −0.0029 (8) | 0.0175 (8) | −0.0063 (9) |
C2A | 0.0524 (10) | 0.0488 (12) | 0.0522 (11) | −0.0010 (8) | 0.0177 (8) | −0.0024 (10) |
C3A | 0.0568 (11) | 0.0387 (11) | 0.0646 (13) | −0.0037 (8) | 0.0171 (9) | −0.0022 (10) |
C4A | 0.0928 (14) | 0.0538 (13) | 0.0700 (13) | −0.0027 (10) | 0.0364 (11) | 0.0080 (10) |
C5A | 0.1300 (18) | 0.0461 (13) | 0.0825 (15) | −0.0051 (11) | 0.0293 (13) | −0.0171 (11) |
C6A | 0.0677 (11) | 0.0376 (11) | 0.0489 (10) | −0.0032 (8) | 0.0186 (9) | −0.0032 (8) |
C7A | 0.0574 (10) | 0.0535 (12) | 0.0613 (11) | −0.0007 (9) | 0.0235 (9) | −0.0124 (9) |
C8A | 0.0584 (10) | 0.0539 (12) | 0.0572 (11) | −0.0091 (8) | 0.0238 (9) | −0.0080 (9) |
C9A | 0.0653 (11) | 0.0437 (11) | 0.0472 (10) | −0.0039 (8) | 0.0227 (9) | −0.0039 (8) |
C10A | 0.0816 (12) | 0.0467 (11) | 0.0599 (11) | −0.0008 (9) | 0.0376 (10) | −0.0066 (9) |
C11A | 0.0808 (12) | 0.0495 (12) | 0.0641 (12) | −0.0078 (9) | 0.0408 (10) | −0.0051 (9) |
C12A | 0.0814 (13) | 0.0500 (12) | 0.0517 (11) | −0.0072 (9) | 0.0316 (10) | −0.0031 (9) |
C13A | 0.0636 (11) | 0.0426 (11) | 0.0510 (10) | −0.0066 (8) | 0.0263 (8) | −0.0025 (9) |
C14A | 0.0744 (12) | 0.0551 (12) | 0.0579 (12) | −0.0060 (9) | 0.0274 (9) | −0.0045 (10) |
C15A | 0.0827 (14) | 0.0865 (17) | 0.0569 (12) | −0.0132 (12) | 0.0282 (10) | −0.0162 (12) |
C16A | 0.0901 (15) | 0.0821 (18) | 0.0897 (17) | −0.0196 (12) | 0.0483 (13) | −0.0388 (14) |
C17A | 0.0954 (15) | 0.0520 (13) | 0.1028 (19) | −0.0019 (11) | 0.0497 (14) | −0.0186 (13) |
C18A | 0.0738 (12) | 0.0510 (12) | 0.0690 (13) | −0.0001 (9) | 0.0305 (10) | 0.0012 (10) |
O1B | 0.1097 (11) | 0.0902 (12) | 0.0804 (11) | −0.0197 (8) | 0.0361 (9) | 0.0111 (9) |
O2B | 0.0975 (10) | 0.0831 (11) | 0.0709 (10) | −0.0008 (8) | 0.0310 (8) | −0.0116 (8) |
O3B | 0.1047 (10) | 0.0693 (10) | 0.0629 (8) | −0.0026 (8) | 0.0275 (7) | −0.0024 (8) |
O4B | 0.213 (2) | 0.0903 (13) | 0.1092 (14) | −0.0686 (14) | 0.0687 (13) | −0.0302 (11) |
N1B | 0.0660 (10) | 0.0685 (12) | 0.0619 (11) | 0.0015 (8) | 0.0201 (8) | −0.0003 (9) |
N2B | 0.0688 (10) | 0.0767 (13) | 0.0666 (11) | −0.0053 (9) | 0.0231 (8) | 0.0011 (10) |
N3B | 0.0715 (11) | 0.0688 (12) | 0.0780 (12) | −0.0047 (8) | 0.0269 (9) | 0.0047 (11) |
C1B | 0.0608 (12) | 0.0661 (15) | 0.0650 (14) | 0.0004 (9) | 0.0154 (10) | −0.0024 (12) |
C2B | 0.0609 (12) | 0.0795 (17) | 0.0681 (14) | −0.0069 (10) | 0.0198 (10) | 0.0024 (13) |
C3B | 0.0532 (11) | 0.0755 (16) | 0.0656 (14) | 0.0002 (10) | 0.0161 (10) | −0.0107 (12) |
C4B | 0.150 (2) | 0.139 (2) | 0.0673 (16) | −0.0316 (18) | 0.0447 (15) | 0.0034 (16) |
C5B | 0.136 (2) | 0.0783 (18) | 0.1087 (19) | −0.0046 (15) | 0.0454 (16) | −0.0319 (15) |
C6B | 0.0755 (13) | 0.0588 (13) | 0.0582 (12) | 0.0025 (10) | 0.0234 (11) | −0.0009 (10) |
C7B | 0.0666 (13) | 0.0813 (15) | 0.0675 (13) | −0.0001 (11) | 0.0130 (10) | −0.0106 (12) |
C8B | 0.0675 (13) | 0.0818 (16) | 0.0790 (15) | −0.0163 (11) | 0.0239 (12) | −0.0166 (13) |
C9B | 0.0745 (13) | 0.0658 (13) | 0.0654 (13) | −0.0110 (10) | 0.0288 (11) | −0.0113 (11) |
C10B | 0.0700 (12) | 0.0705 (14) | 0.0623 (12) | −0.0089 (10) | 0.0201 (10) | −0.0050 (11) |
C11B | 0.0652 (12) | 0.0671 (14) | 0.0678 (13) | −0.0091 (10) | 0.0212 (10) | −0.0046 (11) |
C12B | 0.1004 (16) | 0.0709 (16) | 0.0865 (16) | −0.0227 (12) | 0.0409 (13) | −0.0117 (13) |
C13B | 0.0791 (13) | 0.0752 (16) | 0.0843 (16) | −0.0186 (12) | 0.0342 (12) | 0.0006 (14) |
C14B | 0.0769 (14) | 0.0981 (19) | 0.0734 (15) | −0.0064 (12) | 0.0285 (11) | 0.0000 (14) |
C15B | 0.0930 (17) | 0.129 (2) | 0.0844 (18) | −0.0233 (16) | 0.0424 (14) | −0.0134 (18) |
C16B | 0.121 (2) | 0.153 (3) | 0.0848 (19) | −0.048 (2) | 0.0353 (17) | 0.020 (2) |
C17B | 0.134 (2) | 0.116 (3) | 0.116 (3) | −0.033 (2) | 0.028 (2) | 0.043 (2) |
C18B | 0.121 (2) | 0.0850 (19) | 0.113 (2) | −0.0231 (15) | 0.0441 (17) | 0.0135 (17) |
Geometric parameters (Å, º) top
O1A—C2A | 1.331 (2) | O1B—C2B | 1.329 (2) |
O1A—C4A | 1.444 (2) | O1B—C4B | 1.444 (3) |
O2A—C3A | 1.325 (2) | O2B—C3B | 1.335 (2) |
O2A—C5A | 1.455 (2) | O2B—C5B | 1.444 (2) |
O3A—C1A | 1.3570 (19) | O3B—C1B | 1.346 (2) |
O3A—C6A | 1.4057 (19) | O3B—C6B | 1.398 (2) |
O4A—C12A | 1.225 (2) | O4B—C12B | 1.218 (2) |
N1A—C1A | 1.317 (2) | N1B—C1B | 1.320 (2) |
N1A—C3A | 1.340 (2) | N1B—C3B | 1.345 (3) |
N2A—C1A | 1.325 (2) | N2B—C2B | 1.311 (3) |
N2A—C2A | 1.329 (2) | N2B—C1B | 1.328 (2) |
N3A—C3A | 1.322 (2) | N3B—C3B | 1.317 (2) |
N3A—C2A | 1.326 (2) | N3B—C2B | 1.339 (3) |
C4A—H4A1 | 0.9600 | C4B—H4B1 | 0.9600 |
C4A—H4A2 | 0.9600 | C4B—H4B2 | 0.9600 |
C4A—H4A3 | 0.9600 | C4B—H4B3 | 0.9600 |
C5A—H5A1 | 0.9600 | C5B—H5B1 | 0.9600 |
C5A—H5A2 | 0.9600 | C5B—H5B2 | 0.9600 |
C5A—H5A3 | 0.9600 | C5B—H5B3 | 0.9600 |
C6A—C7A | 1.377 (2) | C6B—C11B | 1.373 (3) |
C6A—C11A | 1.377 (2) | C6B—C7B | 1.375 (3) |
C7A—C8A | 1.375 (2) | C7B—C8B | 1.375 (3) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.387 (2) | C8B—C9B | 1.393 (3) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.384 (2) | C9B—C10B | 1.392 (2) |
C9A—C12A | 1.488 (2) | C9B—C12B | 1.485 (3) |
C10A—C11A | 1.388 (2) | C10B—C11B | 1.379 (2) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.479 (2) | C12B—C13B | 1.479 (3) |
C13A—C14A | 1.383 (2) | C13B—C14B | 1.379 (3) |
C13A—C18A | 1.389 (2) | C13B—C18B | 1.382 (3) |
C14A—C15A | 1.380 (3) | C14B—C15B | 1.386 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.373 (3) | C15B—C16B | 1.351 (4) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.377 (3) | C16B—C17B | 1.374 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—C18A | 1.376 (3) | C17B—C18B | 1.390 (4) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
| | | |
C2A—O1A—C4A | 117.83 (14) | C2B—O1B—C4B | 116.61 (19) |
C3A—O2A—C5A | 117.44 (16) | C3B—O2B—C5B | 117.79 (18) |
C1A—O3A—C6A | 121.09 (14) | C1B—O3B—C6B | 121.90 (16) |
C1A—N1A—C3A | 111.56 (15) | C1B—N1B—C3B | 111.57 (18) |
C1A—N2A—C2A | 112.11 (15) | C2B—N2B—C1B | 112.57 (19) |
C3A—N3A—C2A | 112.72 (15) | C3B—N3B—C2B | 112.49 (19) |
N1A—C1A—N2A | 128.67 (16) | N1B—C1B—N2B | 128.3 (2) |
N1A—C1A—O3A | 112.55 (16) | N1B—C1B—O3B | 119.7 (2) |
N2A—C1A—O3A | 118.76 (15) | N2B—C1B—O3B | 111.97 (19) |
N3A—C2A—N2A | 127.27 (17) | N2B—C2B—O1B | 119.5 (2) |
N3A—C2A—O1A | 113.66 (16) | N2B—C2B—N3B | 127.5 (2) |
N2A—C2A—O1A | 119.08 (16) | O1B—C2B—N3B | 113.0 (2) |
N3A—C3A—O2A | 119.35 (17) | N3B—C3B—O2B | 120.1 (2) |
N3A—C3A—N1A | 127.63 (16) | N3B—C3B—N1B | 127.6 (2) |
O2A—C3A—N1A | 113.01 (17) | O2B—C3B—N1B | 112.3 (2) |
O1A—C4A—H4A1 | 109.5 | O1B—C4B—H4B1 | 109.5 |
O1A—C4A—H4A2 | 109.5 | O1B—C4B—H4B2 | 109.5 |
H4A1—C4A—H4A2 | 109.5 | H4B1—C4B—H4B2 | 109.5 |
O1A—C4A—H4A3 | 109.5 | O1B—C4B—H4B3 | 109.5 |
H4A1—C4A—H4A3 | 109.5 | H4B1—C4B—H4B3 | 109.5 |
H4A2—C4A—H4A3 | 109.5 | H4B2—C4B—H4B3 | 109.5 |
O2A—C5A—H5A1 | 109.5 | O2B—C5B—H5B1 | 109.5 |
O2A—C5A—H5A2 | 109.5 | O2B—C5B—H5B2 | 109.5 |
H5A1—C5A—H5A2 | 109.5 | H5B1—C5B—H5B2 | 109.5 |
O2A—C5A—H5A3 | 109.5 | O2B—C5B—H5B3 | 109.5 |
H5A1—C5A—H5A3 | 109.5 | H5B1—C5B—H5B3 | 109.5 |
H5A2—C5A—H5A3 | 109.5 | H5B2—C5B—H5B3 | 109.5 |
C7A—C6A—C11A | 121.83 (16) | C11B—C6B—C7B | 121.71 (19) |
C7A—C6A—O3A | 122.14 (16) | C11B—C6B—O3B | 122.22 (17) |
C11A—C6A—O3A | 115.85 (16) | C7B—C6B—O3B | 115.73 (17) |
C8A—C7A—C6A | 118.45 (17) | C8B—C7B—C6B | 119.25 (18) |
C8A—C7A—H7A | 120.8 | C8B—C7B—H7B | 120.4 |
C6A—C7A—H7A | 120.8 | C6B—C7B—H7B | 120.4 |
C7A—C8A—C9A | 121.49 (17) | C7B—C8B—C9B | 120.62 (18) |
C7A—C8A—H8A | 119.3 | C7B—C8B—H8B | 119.7 |
C9A—C8A—H8A | 119.3 | C9B—C8B—H8B | 119.7 |
C10A—C9A—C8A | 118.71 (16) | C10B—C9B—C8B | 118.6 (2) |
C10A—C9A—C12A | 122.95 (16) | C10B—C9B—C12B | 120.89 (18) |
C8A—C9A—C12A | 118.25 (16) | C8B—C9B—C12B | 120.37 (18) |
C9A—C10A—C11A | 120.68 (17) | C11B—C10B—C9B | 121.03 (18) |
C9A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.5 |
C11A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.5 |
C6A—C11A—C10A | 118.70 (17) | C6B—C11B—C10B | 118.74 (18) |
C6A—C11A—H11A | 120.6 | C6B—C11B—H11B | 120.6 |
C10A—C11A—H11A | 120.6 | C10B—C11B—H11B | 120.6 |
O4A—C12A—C13A | 119.46 (16) | O4B—C12B—C13B | 120.1 (2) |
O4A—C12A—C9A | 118.78 (16) | O4B—C12B—C9B | 120.5 (2) |
C13A—C12A—C9A | 121.75 (17) | C13B—C12B—C9B | 119.44 (19) |
C14A—C13A—C18A | 118.70 (17) | C14B—C13B—C18B | 119.2 (2) |
C14A—C13A—C12A | 122.27 (16) | C14B—C13B—C12B | 121.4 (2) |
C18A—C13A—C12A | 118.84 (16) | C18B—C13B—C12B | 119.4 (2) |
C15A—C14A—C13A | 120.55 (19) | C13B—C14B—C15B | 121.0 (2) |
C15A—C14A—H14A | 119.7 | C13B—C14B—H14B | 119.5 |
C13A—C14A—H14A | 119.7 | C15B—C14B—H14B | 119.5 |
C16A—C15A—C14A | 120.0 (2) | C16B—C15B—C14B | 119.6 (3) |
C16A—C15A—H15A | 120.0 | C16B—C15B—H15B | 120.2 |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 120.2 |
C15A—C16A—C17A | 120.2 (2) | C15B—C16B—C17B | 120.6 (3) |
C15A—C16A—H16A | 119.9 | C15B—C16B—H16B | 119.7 |
C17A—C16A—H16A | 119.9 | C17B—C16B—H16B | 119.7 |
C18A—C17A—C16A | 119.8 (2) | C16B—C17B—C18B | 120.4 (3) |
C18A—C17A—H17A | 120.1 | C16B—C17B—H17B | 119.8 |
C16A—C17A—H17A | 120.1 | C18B—C17B—H17B | 119.8 |
C17A—C18A—C13A | 120.69 (19) | C13B—C18B—C17B | 119.2 (3) |
C17A—C18A—H18A | 119.7 | C13B—C18B—H18B | 120.4 |
C13A—C18A—H18A | 119.7 | C17B—C18B—H18B | 120.4 |
| | | |
C3A—N1A—C1A—N2A | 2.0 (2) | C3B—N1B—C1B—N2B | −0.4 (3) |
C3A—N1A—C1A—O3A | −179.59 (13) | C3B—N1B—C1B—O3B | 178.61 (15) |
C2A—N2A—C1A—N1A | −2.6 (2) | C2B—N2B—C1B—N1B | 0.7 (3) |
C2A—N2A—C1A—O3A | 179.05 (14) | C2B—N2B—C1B—O3B | −178.44 (15) |
C6A—O3A—C1A—N1A | 169.55 (14) | C6B—O3B—C1B—N1B | −0.9 (3) |
C6A—O3A—C1A—N2A | −11.8 (2) | C6B—O3B—C1B—N2B | 178.31 (15) |
C3A—N3A—C2A—N2A | 0.2 (2) | C1B—N2B—C2B—O1B | 179.22 (16) |
C3A—N3A—C2A—O1A | 180.00 (14) | C1B—N2B—C2B—N3B | −0.6 (3) |
C1A—N2A—C2A—N3A | 1.3 (2) | C4B—O1B—C2B—N2B | −4.7 (3) |
C1A—N2A—C2A—O1A | −178.44 (14) | C4B—O1B—C2B—N3B | 175.11 (18) |
C4A—O1A—C2A—N3A | −176.00 (14) | C3B—N3B—C2B—N2B | 0.4 (3) |
C4A—O1A—C2A—N2A | 3.8 (2) | C3B—N3B—C2B—O1B | −179.48 (15) |
C2A—N3A—C3A—O2A | 179.98 (14) | C2B—N3B—C3B—O2B | 179.67 (16) |
C2A—N3A—C3A—N1A | −1.0 (2) | C2B—N3B—C3B—N1B | −0.1 (3) |
C5A—O2A—C3A—N3A | 2.7 (2) | C5B—O2B—C3B—N3B | −1.3 (3) |
C5A—O2A—C3A—N1A | −176.49 (15) | C5B—O2B—C3B—N1B | 178.46 (16) |
C1A—N1A—C3A—N3A | 0.0 (2) | C1B—N1B—C3B—N3B | 0.1 (3) |
C1A—N1A—C3A—O2A | 179.13 (13) | C1B—N1B—C3B—O2B | −179.66 (15) |
C1A—O3A—C6A—C7A | −44.4 (2) | C1B—O3B—C6B—C11B | 59.4 (3) |
C1A—O3A—C6A—C11A | 140.46 (16) | C1B—O3B—C6B—C7B | −127.12 (18) |
C11A—C6A—C7A—C8A | −3.9 (2) | C11B—C6B—C7B—C8B | 0.6 (3) |
O3A—C6A—C7A—C8A | −178.78 (14) | O3B—C6B—C7B—C8B | −172.84 (18) |
C6A—C7A—C8A—C9A | 2.8 (3) | C6B—C7B—C8B—C9B | −3.1 (3) |
C7A—C8A—C9A—C10A | 0.4 (2) | C7B—C8B—C9B—C10B | 2.9 (3) |
C7A—C8A—C9A—C12A | −176.22 (15) | C7B—C8B—C9B—C12B | 178.0 (2) |
C8A—C9A—C10A—C11A | −2.7 (3) | C8B—C9B—C10B—C11B | −0.2 (3) |
C12A—C9A—C10A—C11A | 173.80 (16) | C12B—C9B—C10B—C11B | −175.34 (19) |
C7A—C6A—C11A—C10A | 1.7 (3) | C7B—C6B—C11B—C10B | 1.9 (3) |
O3A—C6A—C11A—C10A | 176.90 (15) | O3B—C6B—C11B—C10B | 175.00 (17) |
C9A—C10A—C11A—C6A | 1.6 (3) | C9B—C10B—C11B—C6B | −2.1 (3) |
C10A—C9A—C12A—O4A | −144.06 (19) | C10B—C9B—C12B—O4B | 139.7 (2) |
C8A—C9A—C12A—O4A | 32.4 (2) | C8B—C9B—C12B—O4B | −35.3 (3) |
C10A—C9A—C12A—C13A | 36.9 (3) | C10B—C9B—C12B—C13B | −40.8 (3) |
C8A—C9A—C12A—C13A | −146.61 (17) | C8B—C9B—C12B—C13B | 144.1 (2) |
O4A—C12A—C13A—C14A | −146.23 (18) | O4B—C12B—C13B—C14B | 145.5 (2) |
C9A—C12A—C13A—C14A | 32.8 (3) | C9B—C12B—C13B—C14B | −34.0 (3) |
O4A—C12A—C13A—C18A | 28.6 (3) | O4B—C12B—C13B—C18B | −31.7 (3) |
C9A—C12A—C13A—C18A | −152.42 (16) | C9B—C12B—C13B—C18B | 148.8 (2) |
C18A—C13A—C14A—C15A | −0.1 (3) | C18B—C13B—C14B—C15B | 1.2 (3) |
C12A—C13A—C14A—C15A | 174.74 (16) | C12B—C13B—C14B—C15B | −176.0 (2) |
C13A—C14A—C15A—C16A | 0.4 (3) | C13B—C14B—C15B—C16B | −1.5 (3) |
C14A—C15A—C16A—C17A | −0.1 (3) | C14B—C15B—C16B—C17B | 0.2 (4) |
C15A—C16A—C17A—C18A | −0.5 (3) | C15B—C16B—C17B—C18B | 1.5 (4) |
C16A—C17A—C18A—C13A | 0.8 (3) | C14B—C13B—C18B—C17B | 0.4 (3) |
C14A—C13A—C18A—C17A | −0.5 (3) | C12B—C13B—C18B—C17B | 177.7 (2) |
C12A—C13A—C18A—C17A | −175.53 (17) | C16B—C17B—C18B—C13B | −1.7 (4) |
Experimental details
| (I) | (II) | (III) |
Crystal data |
Chemical formula | C9H14N4O3 | C12H13N3O4 | C18H15N3O4 |
Mr | 226.24 | 263.25 | 337.33 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 | Monoclinic, C2/c |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 10.244 (2), 9.208 (3), 11.615 (3) | 7.386 (2), 9.718 (2), 9.868 (2) | 32.610 (6), 13.757 (3), 15.904 (3) |
α, β, γ (°) | 90, 99.70 (3), 90 | 108.73 (2), 93.36 (2), 109.67 (2) | 90, 111.56 (2), 90 |
V (Å3) | 1079.9 (5) | 620.5 (3) | 6636 (2) |
Z | 4 | 2 | 16 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 | 0.10 |
Crystal size (mm) | 0.33 × 0.15 × 0.12 | 0.45 × 0.30 × 0.12 | 0.60 × 0.30 × 0.27 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nnius KappaCCD diffractometer |
Absorption correction | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2944, 1799, 883 | 2195, 2195, 1496 | 11206, 5860, 3022 |
Rint | 0.060 | 0.000 | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 | 0.596 | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.159, 0.98 | 0.042, 0.129, 1.03 | 0.039, 0.100, 0.85 |
No. of reflections | 1799 | 2195 | 5860 |
No. of parameters | 147 | 180 | 456 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 | 0.20, −0.18 | 0.17, −0.14 |
Comparison of selected bond angles (°) top | (I) | (II) | (IIIA) | (IIIB) |
O1-C2-N3 | 113.3 (3) | 113.8 (2) | 113.7 (2) | 113.0 (2) |
O2-C3-N3 | 113.7 (3) | 119.7 (2) | 119.4 (2) | 120.1 (2) |
O1-C2-N2 | 118.7 (3) | 119.1 (2) | 119.1 (2) | 119.5 (2) |
O2-C3-N1 | 118.1 (3) | 112.8 (2) | 113.0 (2) | 112.3 (2) |
N2-C1-C4 | 117.6 (3) | 111.8 (2) | 118.8 (2) | 112.0 (2) |
N1-C1-C4 | 117.8 (3) | 120.5 (2) | | |
N2-C1-O3 | | | 118.8 (2) | 112.0 (2) |
N1-C1-O3 | | | 112.6 (2) | 119.7 (2) |
Selected torsion angles (°) top | (I) | (II) | (IIIA) | (IIIB) |
N2-C2-O1-C4 | -2.3 (4) | 175.7 (2) | 3.8 (2) | -4.7 (2) |
N1-C3-O2-C5 | -2.7 (5) | 1.0 (2) | -176.5 (2) | 178.5 (2) |
N1-C1-N4-C9 | 0.3 (5) | | | |
(N1-C1-O3-C6) | | 3.5 (2) | 169.6 (2) | -0.9 (3) |
C1-O3-C6-C11 | | -98.1 (2) | 140.5 (2) | 59.4 (3) |
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The title compounds, viz. 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)morpholine, (I), 1,3,5-triazine, 2-(2-methyl-3-hydroxy)-4,6-dimethoxy-(9CI), (II), and 2,4-Dimethoxy-6-oxybenzophenone-1,3,5-triazine, (III), have been prepared and studied in order to examine their potential ability to undergo methyl rearrangement in the solid or liquid state (Kaftory & Handelsman-Benory, 1994; Handelsman-Benory et al., 2000; Greenberg et al. 2001; Kaftory et al., 2001; Kaftory, 2002). We investigate here the structure of the three compounds, none of which undergo solid-state rearrangement.
The 4,6-dimethoxy-1,3,5-triazine moiety is common to the three compounds. Comparison of the external-ring bond angles at the two methoxy groups (Table 1) shows that they are strongly affected by the bulky methyl group, so that the bond angle at the same side as? the methyl group is larger by 5–8° than the bond angle at the opposite side. A similar steric effect is also observed at the external-ring bond angle at atom C1, where the substituent are larger groups than methyl (Table 1). These two bond angles are practically equal when the substituent is morpholin [i.e. in (I)], because the molecule has a pseudo-mirror symmetry (Fig. 1), and the differences between the angles is up to 7.7° in (III).
The molecules in (I) are packed in pairs that consist of two molecules related by an inversion center. Translation of pairs of molecules along the a axis forms columns, with each of the columns surrounded by four neighboring columns.
Molecules of (II) (Fig. 2) are packed as dimers formed by O—H···N hydrogen bonds [O4.·N1 = 3.028 (2) Å and O4—H4O.·N1 = 172°; Fig. 3]. The phenyl ring is almost perpendicular to the triazine moiety [C1—O3—C6—C11 = −98.2 (2)°]. The molecules of (II) are packed in such a way that the triazine planes of two neighboring molecules and the phenyl planes of two neighboring molecules are arranged face-to-face.
Compound (III) crystallizes with two crystallographically non-equivalent molecules. The two molecules adopt completely different conformations (Figs. 4 and 5); molecule A has a rod shape while molecule B is folded. Relevant torsion angles are given in Table 2. The molecules are stacked along the a axis.
The morpholin moiety in (I) adopts a chair conformation, and the triazine moiety adopts a butterfly conformation with respect to the two methoxy groups, as was found in 2-(4'-nitroanilino) 4,6-dimethoxy-1,3,5-triazine (Taycher et al., 2001). The same moiety in (II) and (III) adopts a propeller conformation. The torsion angles are given in Table 2.