Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045035/sj2356sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045035/sj2356Isup2.hkl |
CCDC reference: 664207
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.102
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
For the preparation and uses of (I) and similar compounds, see: Borzatta & Carrozza (1991); Deng et al. (2006); Kaiser & Thurston (1951).
The title compound was prepared according to the method of Kaiser & Thurston (1951) in 74.5% yield. Crystals of (I) were obtained by slow evaporation of a solution in methanol (m.p. 473–475 K).
The amine H atoms were located in a Fourier map and refined freely with isotropic displacement parameters. All other H atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq (C) for CH, 0.99 Å, Uiso = 1.2Ueq (C) for CH2 and 0.98 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) the piperidine ring adopts a chair conformation and the triazine ring is essentially planar with an r.m.s. deviation from the mean plane of 0.0115Å. In the crystal structure N—H···N hydrogen bonds link the molecules into chains along b</>, Table 1.
For the preparation and uses of (I) 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: CrystalStructure (Version 3.7.0; Rigaku/MSC, 2005).
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 with arbitrary radii. |
C20H37ClN6 | F(000) = 864 |
Mr = 397.01 | Dx = 1.189 Mg m−3 |
Monoclinic, P21/n | Melting point: 473-475 K K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71070 Å |
a = 7.9906 (7) Å | Cell parameters from 7832 reflections |
b = 20.5197 (16) Å | θ = 1.5–27.9° |
c = 13.6338 (10) Å | µ = 0.19 mm−1 |
β = 97.273 (3)° | T = 113 K |
V = 2217.5 (3) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.22 × 0.20 mm |
Rigaku Saturn CCD diffractometer | 5297 independent reflections |
Radiation source: rotating anode | 4972 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.035 |
Detector resolution: 14.63 pixels mm-1 | θmax = 27.9°, θmin = 1.8° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −26→27 |
Tmin = 0.943, Tmax = 0.963 | l = −17→17 |
27567 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6837P] where P = (Fo2 + 2Fc2)/3 |
5297 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C20H37ClN6 | V = 2217.5 (3) Å3 |
Mr = 397.01 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.9906 (7) Å | µ = 0.19 mm−1 |
b = 20.5197 (16) Å | T = 113 K |
c = 13.6338 (10) Å | 0.26 × 0.22 × 0.20 mm |
β = 97.273 (3)° |
Rigaku Saturn CCD diffractometer | 5297 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 4972 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.963 | Rint = 0.035 |
27567 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.26 e Å−3 |
5297 reflections | Δρmin = −0.27 e Å−3 |
265 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 | ||
Cl1 | 0.01081 (4) | 0.699625 (15) | 0.47224 (2) | 0.02317 (10) | |
N1 | 0.15950 (13) | 0.66230 (5) | 0.32523 (8) | 0.0168 (2) | |
N2 | 0.09387 (13) | 0.57989 (5) | 0.43869 (8) | 0.0173 (2) | |
N3 | 0.22982 (13) | 0.55103 (5) | 0.29729 (8) | 0.0155 (2) | |
N4 | 0.28136 (14) | 0.63301 (5) | 0.18846 (8) | 0.0170 (2) | |
N5 | 0.17778 (15) | 0.47447 (5) | 0.41161 (8) | 0.0204 (2) | |
N6 | 0.28530 (14) | 0.28875 (5) | 0.29972 (8) | 0.0175 (2) | |
C1 | 0.22279 (15) | 0.61388 (6) | 0.27161 (9) | 0.0149 (2) | |
C2 | 0.09911 (16) | 0.63977 (6) | 0.40412 (9) | 0.0162 (2) | |
C3 | 0.16769 (15) | 0.53637 (6) | 0.38127 (9) | 0.0159 (2) | |
C4 | 0.33522 (16) | 0.59015 (6) | 0.11107 (9) | 0.0173 (3) | |
C5 | 0.48819 (15) | 0.54635 (6) | 0.14791 (9) | 0.0165 (2) | |
H5A | 0.4449 | 0.5120 | 0.1890 | 0.020* | |
H5B | 0.5207 | 0.5242 | 0.0886 | 0.020* | |
C6 | 0.65409 (16) | 0.57120 (6) | 0.20685 (10) | 0.0197 (3) | |
C7 | 0.37084 (19) | 0.63562 (7) | 0.02693 (10) | 0.0248 (3) | |
H7A | 0.2657 | 0.6567 | −0.0015 | 0.037* | |
H7B | 0.4170 | 0.6103 | −0.0244 | 0.037* | |
H7C | 0.4526 | 0.6689 | 0.0528 | 0.037* | |
C8 | 0.18857 (17) | 0.54531 (7) | 0.07119 (10) | 0.0228 (3) | |
H8A | 0.1592 | 0.5172 | 0.1246 | 0.034* | |
H8B | 0.2223 | 0.5183 | 0.0178 | 0.034* | |
H8C | 0.0906 | 0.5718 | 0.0457 | 0.034* | |
C9 | 0.63165 (19) | 0.59348 (8) | 0.31157 (11) | 0.0317 (3) | |
H9A | 0.7423 | 0.6028 | 0.3485 | 0.048* | |
H9B | 0.5762 | 0.5589 | 0.3452 | 0.048* | |
H9C | 0.5620 | 0.6329 | 0.3080 | 0.048* | |
C10 | 0.77338 (18) | 0.51252 (7) | 0.21771 (11) | 0.0271 (3) | |
H10A | 0.7925 | 0.4971 | 0.1520 | 0.041* | |
H10B | 0.7228 | 0.4775 | 0.2530 | 0.041* | |
H10C | 0.8812 | 0.5254 | 0.2550 | 0.041* | |
C11 | 0.7392 (2) | 0.62547 (8) | 0.15494 (14) | 0.0375 (4) | |
H11A | 0.6733 | 0.6657 | 0.1562 | 0.056* | |
H11B | 0.7459 | 0.6129 | 0.0862 | 0.056* | |
H11C | 0.8532 | 0.6327 | 0.1890 | 0.056* | |
C12 | 0.24318 (17) | 0.42220 (6) | 0.35383 (9) | 0.0187 (3) | |
H12 | 0.3114 | 0.4423 | 0.3051 | 0.022* | |
C13 | 0.09877 (17) | 0.38406 (6) | 0.29721 (10) | 0.0200 (3) | |
H13A | 0.0288 | 0.4142 | 0.2524 | 0.024* | |
H13B | 0.0268 | 0.3662 | 0.3447 | 0.024* | |
C14 | 0.15876 (17) | 0.32805 (6) | 0.23626 (9) | 0.0194 (3) | |
C15 | 0.42659 (16) | 0.32117 (6) | 0.36202 (10) | 0.0187 (3) | |
C16 | 0.35639 (17) | 0.37652 (6) | 0.42026 (10) | 0.0191 (3) | |
H16A | 0.2913 | 0.3577 | 0.4705 | 0.023* | |
H16B | 0.4514 | 0.4017 | 0.4553 | 0.023* | |
C17 | 0.2212 (2) | 0.35397 (7) | 0.14140 (10) | 0.0279 (3) | |
H17A | 0.3049 | 0.3884 | 0.1585 | 0.042* | |
H17B | 0.1256 | 0.3717 | 0.0974 | 0.042* | |
H17C | 0.2728 | 0.3183 | 0.1080 | 0.042* | |
C18 | 0.00934 (19) | 0.28255 (7) | 0.20586 (11) | 0.0268 (3) | |
H18A | 0.0459 | 0.2464 | 0.1668 | 0.040* | |
H18B | −0.0808 | 0.3068 | 0.1662 | 0.040* | |
H18C | −0.0327 | 0.2654 | 0.2652 | 0.040* | |
C19 | 0.56744 (18) | 0.34602 (7) | 0.30424 (12) | 0.0293 (3) | |
H19A | 0.6053 | 0.3104 | 0.2644 | 0.044* | |
H19B | 0.6625 | 0.3616 | 0.3508 | 0.044* | |
H19C | 0.5241 | 0.3818 | 0.2607 | 0.044* | |
C20 | 0.50283 (18) | 0.26939 (7) | 0.43525 (11) | 0.0258 (3) | |
H20A | 0.4158 | 0.2532 | 0.4737 | 0.039* | |
H20B | 0.5953 | 0.2886 | 0.4801 | 0.039* | |
H20C | 0.5462 | 0.2332 | 0.3989 | 0.039* | |
H4 | 0.2754 (19) | 0.6750 (8) | 0.1757 (11) | 0.023 (4)* | |
H6 | 0.328 (2) | 0.2611 (8) | 0.2589 (12) | 0.028 (4)* | |
H5 | 0.121 (2) | 0.4641 (8) | 0.4594 (12) | 0.026 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03026 (19) | 0.01401 (16) | 0.02806 (18) | 0.00117 (12) | 0.01467 (14) | −0.00363 (12) |
N1 | 0.0180 (5) | 0.0129 (5) | 0.0204 (5) | 0.0004 (4) | 0.0057 (4) | −0.0004 (4) |
N2 | 0.0212 (5) | 0.0138 (5) | 0.0183 (5) | 0.0006 (4) | 0.0073 (4) | −0.0011 (4) |
N3 | 0.0178 (5) | 0.0128 (5) | 0.0167 (5) | 0.0009 (4) | 0.0051 (4) | 0.0011 (4) |
N4 | 0.0208 (5) | 0.0124 (5) | 0.0186 (5) | 0.0018 (4) | 0.0060 (4) | 0.0022 (4) |
N5 | 0.0312 (6) | 0.0139 (5) | 0.0188 (5) | 0.0035 (5) | 0.0135 (5) | 0.0016 (4) |
N6 | 0.0214 (6) | 0.0127 (5) | 0.0185 (5) | 0.0032 (4) | 0.0036 (4) | −0.0010 (4) |
C1 | 0.0132 (6) | 0.0148 (6) | 0.0169 (6) | 0.0001 (5) | 0.0022 (5) | 0.0000 (5) |
C2 | 0.0164 (6) | 0.0144 (6) | 0.0184 (6) | 0.0001 (5) | 0.0040 (5) | −0.0029 (5) |
C3 | 0.0173 (6) | 0.0138 (6) | 0.0171 (6) | 0.0000 (5) | 0.0037 (5) | −0.0006 (4) |
C4 | 0.0195 (6) | 0.0188 (6) | 0.0143 (6) | 0.0019 (5) | 0.0044 (5) | 0.0008 (5) |
C5 | 0.0178 (6) | 0.0161 (6) | 0.0161 (6) | 0.0010 (5) | 0.0045 (5) | −0.0003 (5) |
C6 | 0.0179 (6) | 0.0200 (6) | 0.0214 (6) | −0.0005 (5) | 0.0039 (5) | −0.0004 (5) |
C7 | 0.0284 (7) | 0.0280 (7) | 0.0192 (6) | 0.0055 (6) | 0.0074 (5) | 0.0071 (5) |
C8 | 0.0198 (6) | 0.0284 (7) | 0.0196 (6) | 0.0013 (5) | 0.0005 (5) | −0.0031 (5) |
C9 | 0.0218 (7) | 0.0440 (9) | 0.0281 (8) | 0.0038 (6) | −0.0022 (6) | −0.0143 (7) |
C10 | 0.0205 (7) | 0.0291 (8) | 0.0307 (7) | 0.0056 (6) | −0.0004 (6) | −0.0020 (6) |
C11 | 0.0247 (8) | 0.0372 (9) | 0.0492 (10) | −0.0104 (7) | −0.0008 (7) | 0.0141 (7) |
C12 | 0.0276 (7) | 0.0120 (6) | 0.0183 (6) | 0.0031 (5) | 0.0100 (5) | −0.0003 (5) |
C13 | 0.0250 (7) | 0.0171 (6) | 0.0184 (6) | 0.0066 (5) | 0.0041 (5) | 0.0020 (5) |
C14 | 0.0267 (7) | 0.0156 (6) | 0.0161 (6) | 0.0043 (5) | 0.0028 (5) | 0.0012 (5) |
C15 | 0.0187 (6) | 0.0143 (6) | 0.0236 (6) | 0.0015 (5) | 0.0048 (5) | −0.0004 (5) |
C16 | 0.0212 (6) | 0.0156 (6) | 0.0210 (6) | −0.0008 (5) | 0.0044 (5) | −0.0016 (5) |
C17 | 0.0453 (9) | 0.0215 (7) | 0.0179 (6) | 0.0063 (6) | 0.0084 (6) | 0.0019 (5) |
C18 | 0.0296 (8) | 0.0247 (7) | 0.0245 (7) | 0.0015 (6) | −0.0030 (6) | −0.0013 (6) |
C19 | 0.0251 (7) | 0.0248 (7) | 0.0407 (8) | 0.0007 (6) | 0.0148 (6) | −0.0015 (6) |
C20 | 0.0243 (7) | 0.0201 (7) | 0.0317 (7) | 0.0037 (5) | −0.0012 (6) | 0.0015 (6) |
Cl1—C2 | 1.7420 (12) | C9—H9C | 0.9800 |
N1—C2 | 1.3171 (16) | C10—H10A | 0.9800 |
N1—C1 | 1.3679 (16) | C10—H10B | 0.9800 |
N2—C2 | 1.3185 (16) | C10—H10C | 0.9800 |
N2—C3 | 1.3695 (16) | C11—H11A | 0.9800 |
N3—C1 | 1.3358 (16) | C11—H11B | 0.9800 |
N3—C3 | 1.3386 (15) | C11—H11C | 0.9800 |
N4—C1 | 1.3389 (16) | C12—C16 | 1.5198 (18) |
N4—C4 | 1.4789 (16) | C12—C13 | 1.5212 (19) |
N4—H4 | 0.880 (17) | C12—H12 | 1.0000 |
N5—C3 | 1.3351 (16) | C13—C14 | 1.5305 (17) |
N5—C12 | 1.4658 (16) | C13—H13A | 0.9900 |
N5—H5 | 0.866 (17) | C13—H13B | 0.9900 |
N6—C15 | 1.4819 (17) | C14—C18 | 1.5310 (19) |
N6—C14 | 1.4832 (16) | C14—C17 | 1.5387 (18) |
N6—H6 | 0.893 (17) | C15—C20 | 1.5307 (18) |
C4—C7 | 1.5331 (17) | C15—C16 | 1.5323 (17) |
C4—C8 | 1.5343 (18) | C15—C19 | 1.5400 (18) |
C4—C5 | 1.5487 (17) | C16—H16A | 0.9900 |
C5—C6 | 1.5471 (18) | C16—H16B | 0.9900 |
C5—H5A | 0.9900 | C17—H17A | 0.9800 |
C5—H5B | 0.9900 | C17—H17B | 0.9800 |
C6—C11 | 1.525 (2) | C17—H17C | 0.9800 |
C6—C9 | 1.5312 (19) | C18—H18A | 0.9800 |
C6—C10 | 1.5312 (19) | C18—H18B | 0.9800 |
C7—H7A | 0.9800 | C18—H18C | 0.9800 |
C7—H7B | 0.9800 | C19—H19A | 0.9800 |
C7—H7C | 0.9800 | C19—H19B | 0.9800 |
C8—H8A | 0.9800 | C19—H19C | 0.9800 |
C8—H8B | 0.9800 | C20—H20A | 0.9800 |
C8—H8C | 0.9800 | C20—H20B | 0.9800 |
C9—H9A | 0.9800 | C20—H20C | 0.9800 |
C9—H9B | 0.9800 | ||
C2—N1—C1 | 112.33 (10) | H10B—C10—H10C | 109.5 |
C2—N2—C3 | 111.59 (10) | C6—C11—H11A | 109.5 |
C1—N3—C3 | 115.68 (10) | C6—C11—H11B | 109.5 |
C1—N4—C4 | 126.45 (11) | H11A—C11—H11B | 109.5 |
C1—N4—H4 | 116.0 (10) | C6—C11—H11C | 109.5 |
C4—N4—H4 | 117.1 (10) | H11A—C11—H11C | 109.5 |
C3—N5—C12 | 122.77 (11) | H11B—C11—H11C | 109.5 |
C3—N5—H5 | 116.8 (11) | N5—C12—C16 | 110.90 (10) |
C12—N5—H5 | 118.7 (11) | N5—C12—C13 | 110.48 (10) |
C15—N6—C14 | 120.26 (10) | C16—C12—C13 | 109.95 (10) |
C15—N6—H6 | 108.5 (10) | N5—C12—H12 | 108.5 |
C14—N6—H6 | 105.6 (10) | C16—C12—H12 | 108.5 |
N3—C1—N4 | 119.83 (11) | C13—C12—H12 | 108.5 |
N3—C1—N1 | 124.57 (11) | C12—C13—C14 | 113.09 (11) |
N4—C1—N1 | 115.60 (11) | C12—C13—H13A | 109.0 |
N1—C2—N2 | 130.58 (11) | C14—C13—H13A | 109.0 |
N1—C2—Cl1 | 113.76 (9) | C12—C13—H13B | 109.0 |
N2—C2—Cl1 | 115.66 (9) | C14—C13—H13B | 109.0 |
N5—C3—N3 | 117.67 (11) | H13A—C13—H13B | 107.8 |
N5—C3—N2 | 117.18 (11) | N6—C14—C13 | 109.20 (10) |
N3—C3—N2 | 125.15 (11) | N6—C14—C18 | 106.08 (10) |
N4—C4—C7 | 105.68 (10) | C13—C14—C18 | 108.54 (11) |
N4—C4—C8 | 109.35 (10) | N6—C14—C17 | 114.12 (11) |
C7—C4—C8 | 107.80 (11) | C13—C14—C17 | 110.72 (11) |
N4—C4—C5 | 113.75 (10) | C18—C14—C17 | 107.94 (11) |
C7—C4—C5 | 112.47 (10) | N6—C15—C20 | 105.88 (10) |
C8—C4—C5 | 107.63 (10) | N6—C15—C16 | 109.11 (10) |
C6—C5—C4 | 124.50 (11) | C20—C15—C16 | 108.55 (11) |
C6—C5—H5A | 106.2 | N6—C15—C19 | 114.11 (11) |
C4—C5—H5A | 106.2 | C20—C15—C19 | 107.89 (11) |
C6—C5—H5B | 106.2 | C16—C15—C19 | 111.03 (11) |
C4—C5—H5B | 106.2 | C12—C16—C15 | 112.19 (10) |
H5A—C5—H5B | 106.4 | C12—C16—H16A | 109.2 |
C11—C6—C9 | 109.06 (13) | C15—C16—H16A | 109.2 |
C11—C6—C10 | 108.07 (12) | C12—C16—H16B | 109.2 |
C9—C6—C10 | 106.83 (12) | C15—C16—H16B | 109.2 |
C11—C6—C5 | 113.76 (11) | H16A—C16—H16B | 107.9 |
C9—C6—C5 | 112.89 (11) | C14—C17—H17A | 109.5 |
C10—C6—C5 | 105.84 (11) | C14—C17—H17B | 109.5 |
C4—C7—H7A | 109.5 | H17A—C17—H17B | 109.5 |
C4—C7—H7B | 109.5 | C14—C17—H17C | 109.5 |
H7A—C7—H7B | 109.5 | H17A—C17—H17C | 109.5 |
C4—C7—H7C | 109.5 | H17B—C17—H17C | 109.5 |
H7A—C7—H7C | 109.5 | C14—C18—H18A | 109.5 |
H7B—C7—H7C | 109.5 | C14—C18—H18B | 109.5 |
C4—C8—H8A | 109.5 | H18A—C18—H18B | 109.5 |
C4—C8—H8B | 109.5 | C14—C18—H18C | 109.5 |
H8A—C8—H8B | 109.5 | H18A—C18—H18C | 109.5 |
C4—C8—H8C | 109.5 | H18B—C18—H18C | 109.5 |
H8A—C8—H8C | 109.5 | C15—C19—H19A | 109.5 |
H8B—C8—H8C | 109.5 | C15—C19—H19B | 109.5 |
C6—C9—H9A | 109.5 | H19A—C19—H19B | 109.5 |
C6—C9—H9B | 109.5 | C15—C19—H19C | 109.5 |
H9A—C9—H9B | 109.5 | H19A—C19—H19C | 109.5 |
C6—C9—H9C | 109.5 | H19B—C19—H19C | 109.5 |
H9A—C9—H9C | 109.5 | C15—C20—H20A | 109.5 |
H9B—C9—H9C | 109.5 | C15—C20—H20B | 109.5 |
C6—C10—H10A | 109.5 | H20A—C20—H20B | 109.5 |
C6—C10—H10B | 109.5 | C15—C20—H20C | 109.5 |
H10A—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
C6—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
H10A—C10—H10C | 109.5 | ||
C3—N3—C1—N4 | −179.70 (11) | C4—C5—C6—C11 | −55.96 (17) |
C3—N3—C1—N1 | 0.73 (18) | C4—C5—C6—C9 | 69.01 (16) |
C4—N4—C1—N3 | 8.97 (19) | C4—C5—C6—C10 | −174.47 (11) |
C4—N4—C1—N1 | −171.43 (11) | C3—N5—C12—C16 | 138.28 (13) |
C2—N1—C1—N3 | −2.54 (17) | C3—N5—C12—C13 | −99.54 (14) |
C2—N1—C1—N4 | 177.87 (11) | N5—C12—C13—C14 | −179.25 (10) |
C1—N1—C2—N2 | 1.44 (19) | C16—C12—C13—C14 | −56.51 (14) |
C1—N1—C2—Cl1 | −177.96 (8) | C15—N6—C14—C13 | −48.00 (15) |
C3—N2—C2—N1 | 1.3 (2) | C15—N6—C14—C18 | −164.79 (11) |
C3—N2—C2—Cl1 | −179.28 (9) | C15—N6—C14—C17 | 76.50 (15) |
C12—N5—C3—N3 | −4.09 (19) | C12—C13—C14—N6 | 49.64 (14) |
C12—N5—C3—N2 | 175.73 (11) | C12—C13—C14—C18 | 164.86 (11) |
C1—N3—C3—N5 | −177.61 (11) | C12—C13—C14—C17 | −76.83 (14) |
C1—N3—C3—N2 | 2.58 (18) | C14—N6—C15—C20 | 165.88 (11) |
C2—N2—C3—N5 | 176.71 (12) | C14—N6—C15—C16 | 49.23 (15) |
C2—N2—C3—N3 | −3.48 (18) | C14—N6—C15—C19 | −75.61 (14) |
C1—N4—C4—C7 | 173.46 (12) | N5—C12—C16—C15 | 179.88 (10) |
C1—N4—C4—C8 | 57.68 (16) | C13—C12—C16—C15 | 57.39 (14) |
C1—N4—C4—C5 | −62.67 (16) | N6—C15—C16—C12 | −51.79 (14) |
N4—C4—C5—C6 | −49.78 (16) | C20—C15—C16—C12 | −166.74 (11) |
C7—C4—C5—C6 | 70.32 (15) | C19—C15—C16—C12 | 74.83 (14) |
C8—C4—C5—C6 | −171.09 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N2i | 0.866 (17) | 2.510 (17) | 3.3531 (15) | 164.7 (14) |
N6—H6···N1ii | 0.893 (17) | 2.337 (17) | 3.1653 (15) | 154.2 (14) |
N4—H4···N6iii | 0.880 (17) | 2.415 (17) | 3.2470 (15) | 157.9 (14) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H37ClN6 |
Mr | 397.01 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 113 |
a, b, c (Å) | 7.9906 (7), 20.5197 (16), 13.6338 (10) |
β (°) | 97.273 (3) |
V (Å3) | 2217.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.26 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Rigaku Saturn CCD |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.943, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27567, 5297, 4972 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.102, 1.09 |
No. of reflections | 5297 |
No. of parameters | 265 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.27 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), CrystalStructure (Version 3.7.0; Rigaku/MSC, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N2i | 0.866 (17) | 2.510 (17) | 3.3531 (15) | 164.7 (14) |
N6—H6···N1ii | 0.893 (17) | 2.337 (17) | 3.1653 (15) | 154.2 (14) |
N4—H4···N6iii | 0.880 (17) | 2.415 (17) | 3.2470 (15) | 157.9 (14) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
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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) the piperidine ring adopts a chair conformation and the triazine ring is essentially planar with an r.m.s. deviation from the mean plane of 0.0115Å. In the crystal structure N—H···N hydrogen bonds link the molecules into chains along b</>, Table 1.