Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037877/bt2461sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037877/bt2461Isup2.hkl |
CCDC reference: 660216
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.100
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C2 .. 5.23 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see Borzatta & Carrozza (1991). For related structures, see Deng et al. (2006).
For related literature, see: Kaiser & Thurston (1951).
The title compound was obtained according to the method of Kaiser & Thurston (1951). 2,4,6-Trichloro-1,3,5-triazine (40.0 g, 0.217 mol) was dissolved in toluene (120 ml) and then cooled to 278 K. With stirring, a solution of 2,2,6,6-tetramethylpiperidin-4-amine(33.23 g, 0.213 mol) in toluene (50 ml) was then added dropwise to the mixture over a period of 0.5 h. Then a solution of Na2CO3 (23.02 g, 0.217 mol) in water (50 ml) was then added dropwise for 0.5 h. The mixture was stirred at 273–278 K for further 3 h. The organic layer was washed with water and then concentrated in vacuo. 4,6-dichloro-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazin-2-amine (60.88 g) was obtained in powder form in a yield of 85.0%. Crystals were obtained by slow evaporation of a solution of methanol.
H atoms bonded to C were positioned geometrically (C—H=0.96–0.97 Å), and refined as riding with Uiso(H)=1.2Ueq(C) or 1.5eq(Cmethyl). The methyl groups were allowed to rotate but not to tip. H atoms bonded to N were freely refined.
The title compound is an intermediate for the synthesis of hindered light stabilizers (Borzatta & Carrozza, 1991). Its derivatives have many applications in organic chemistry (Deng et al., 2006).
The triazine ring is essentially planar with an r.m.s. deviation from the mean plane of 0.0038 Å. The molecules are linked by intermolecular N—H···Cl hydrogen bonds (Table 1) forming zigzag chains.
For general background, see Borzatta & Carrozza (1991). For related structures, see Deng et al. (2006).
For related literature, see: Kaiser & Thurston (1951).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.
Fig. 1. A view of the molecular structure of the title compound. Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
C13H23ClN5O+·Cl− | F(000) = 712 |
Mr = 336.26 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7987 (16) Å | Cell parameters from 2231 reflections |
b = 8.9425 (18) Å | θ = 2.3–25.0° |
c = 24.472 (5) Å | µ = 0.39 mm−1 |
β = 90.36 (3)° | T = 113 K |
V = 1706.7 (6) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.26 × 0.22 mm |
Rigaku Saturn diffractometer | 3338 independent reflections |
Radiation source: rotating anode | 3184 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.026 |
Detector resolution: 7.31 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω and φ scans | h = −9→9 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −11→10 |
Tmin = 0.893, Tmax = 0.920 | l = −30→30 |
13533 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0422P)2 + 1.4811P] where P = (Fo2 + 2Fc2)/3 |
3338 reflections | (Δ/σ)max = 0.003 |
207 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C13H23ClN5O+·Cl− | V = 1706.7 (6) Å3 |
Mr = 336.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.7987 (16) Å | µ = 0.39 mm−1 |
b = 8.9425 (18) Å | T = 113 K |
c = 24.472 (5) Å | 0.30 × 0.26 × 0.22 mm |
β = 90.36 (3)° |
Rigaku Saturn diffractometer | 3338 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 3184 reflections with I > 2σ(I) |
Tmin = 0.893, Tmax = 0.920 | Rint = 0.026 |
13533 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.73 e Å−3 |
3338 reflections | Δρmin = −0.38 e Å−3 |
207 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 | 0.81987 (7) | 1.44507 (5) | 0.04206 (2) | 0.02810 (15) | |
O1 | 0.8043 (2) | 0.94806 (17) | −0.03288 (6) | 0.0332 (4) | |
C1 | 0.7679 (3) | 0.7961 (3) | −0.03155 (10) | 0.0363 (5) | |
H1A | 0.8330 | 0.7497 | −0.0028 | 0.054* | |
H1B | 0.7979 | 0.7517 | −0.0659 | 0.054* | |
H1C | 0.6477 | 0.7818 | −0.0251 | 0.054* | |
Cl2 | 0.39494 (7) | 0.25965 (5) | 0.22079 (2) | 0.02840 (15) | |
N1 | 0.6796 (2) | 1.21886 (18) | 0.09038 (7) | 0.0225 (4) | |
N2 | 0.8057 (2) | 1.17694 (19) | 0.00360 (7) | 0.0248 (4) | |
N3 | 0.6822 (2) | 0.97133 (19) | 0.05197 (7) | 0.0232 (4) | |
N4 | 0.5635 (2) | 1.02010 (19) | 0.13604 (7) | 0.0225 (4) | |
H4 | 0.533 (3) | 1.085 (3) | 0.1578 (10) | 0.031 (6)* | |
N5 | 0.3789 (2) | 0.61101 (18) | 0.20083 (6) | 0.0158 (3) | |
C2 | 0.7615 (3) | 1.0330 (2) | 0.00984 (8) | 0.0239 (4) | |
C3 | 0.7600 (2) | 1.2577 (2) | 0.04591 (8) | 0.0219 (4) | |
C4 | 0.6431 (2) | 1.0695 (2) | 0.09169 (8) | 0.0215 (4) | |
C5 | 0.5324 (2) | 0.8625 (2) | 0.14724 (7) | 0.0189 (4) | |
H5 | 0.6095 | 0.8027 | 0.1245 | 0.023* | |
C6 | 0.5720 (2) | 0.8292 (2) | 0.20701 (8) | 0.0203 (4) | |
H6A | 0.4947 | 0.8863 | 0.2298 | 0.024* | |
H6B | 0.6881 | 0.8612 | 0.2153 | 0.024* | |
C7 | 0.5540 (2) | 0.6633 (2) | 0.22059 (7) | 0.0178 (4) | |
C8 | 0.6969 (2) | 0.5703 (2) | 0.19527 (8) | 0.0236 (4) | |
H8A | 0.6676 | 0.4661 | 0.1972 | 0.035* | |
H8B | 0.8021 | 0.5875 | 0.2149 | 0.035* | |
H8C | 0.7111 | 0.5986 | 0.1577 | 0.035* | |
C9 | 0.5543 (3) | 0.6403 (2) | 0.28253 (8) | 0.0254 (4) | |
H9A | 0.4610 | 0.6952 | 0.2983 | 0.038* | |
H9B | 0.6608 | 0.6756 | 0.2976 | 0.038* | |
H9C | 0.5413 | 0.5359 | 0.2905 | 0.038* | |
C10 | 0.3192 (2) | 0.6498 (2) | 0.14307 (7) | 0.0187 (4) | |
C11 | 0.4114 (3) | 0.5538 (2) | 0.10096 (8) | 0.0259 (4) | |
H11A | 0.3499 | 0.5574 | 0.0669 | 0.039* | |
H11B | 0.4167 | 0.4523 | 0.1136 | 0.039* | |
H11C | 0.5255 | 0.5912 | 0.0959 | 0.039* | |
C12 | 0.1282 (3) | 0.6144 (2) | 0.14119 (9) | 0.0301 (5) | |
H12A | 0.0703 | 0.6708 | 0.1689 | 0.045* | |
H12B | 0.1113 | 0.5095 | 0.1475 | 0.045* | |
H12C | 0.0826 | 0.6405 | 0.1059 | 0.045* | |
C13 | 0.3487 (2) | 0.8168 (2) | 0.13443 (8) | 0.0199 (4) | |
H13A | 0.3221 | 0.8421 | 0.0968 | 0.024* | |
H13B | 0.2715 | 0.8727 | 0.1577 | 0.024* | |
H5A | 0.375 (3) | 0.516 (3) | 0.2050 (8) | 0.020 (5)* | |
H5B | 0.307 (3) | 0.649 (3) | 0.2227 (10) | 0.030 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0336 (3) | 0.0207 (3) | 0.0301 (3) | −0.00790 (19) | 0.0058 (2) | 0.00253 (18) |
O1 | 0.0408 (9) | 0.0347 (9) | 0.0240 (7) | 0.0047 (7) | 0.0050 (6) | 0.0038 (6) |
C1 | 0.0308 (12) | 0.0306 (12) | 0.0474 (14) | 0.0022 (9) | −0.0033 (10) | −0.0169 (10) |
Cl2 | 0.0318 (3) | 0.0169 (2) | 0.0367 (3) | −0.00237 (18) | 0.0135 (2) | 0.00176 (19) |
N1 | 0.0243 (8) | 0.0185 (8) | 0.0247 (8) | −0.0038 (6) | 0.0008 (7) | 0.0033 (6) |
N2 | 0.0283 (9) | 0.0219 (8) | 0.0243 (8) | −0.0009 (7) | 0.0002 (7) | 0.0019 (7) |
N3 | 0.0235 (8) | 0.0236 (8) | 0.0225 (8) | −0.0002 (7) | −0.0005 (7) | 0.0036 (7) |
N4 | 0.0292 (9) | 0.0151 (8) | 0.0233 (8) | −0.0030 (7) | 0.0054 (7) | 0.0011 (7) |
N5 | 0.0155 (7) | 0.0135 (8) | 0.0183 (8) | −0.0011 (6) | 0.0021 (6) | 0.0013 (6) |
C2 | 0.0261 (10) | 0.0256 (10) | 0.0199 (9) | 0.0036 (8) | −0.0035 (8) | −0.0008 (8) |
C3 | 0.0210 (9) | 0.0217 (10) | 0.0230 (10) | −0.0031 (7) | −0.0023 (8) | 0.0040 (7) |
C4 | 0.0192 (9) | 0.0223 (10) | 0.0230 (9) | −0.0017 (7) | −0.0015 (7) | 0.0042 (8) |
C5 | 0.0212 (9) | 0.0146 (9) | 0.0209 (9) | −0.0018 (7) | 0.0020 (7) | 0.0026 (7) |
C6 | 0.0208 (9) | 0.0180 (9) | 0.0222 (9) | −0.0048 (7) | −0.0042 (7) | −0.0002 (7) |
C7 | 0.0148 (8) | 0.0186 (9) | 0.0200 (9) | −0.0029 (7) | −0.0024 (7) | 0.0008 (7) |
C8 | 0.0177 (9) | 0.0234 (10) | 0.0298 (10) | 0.0020 (7) | 0.0013 (8) | 0.0048 (8) |
C9 | 0.0292 (10) | 0.0259 (10) | 0.0210 (10) | 0.0000 (8) | −0.0049 (8) | 0.0031 (8) |
C10 | 0.0181 (9) | 0.0201 (9) | 0.0180 (9) | −0.0031 (7) | −0.0030 (7) | 0.0005 (7) |
C11 | 0.0342 (11) | 0.0228 (10) | 0.0208 (9) | −0.0035 (8) | −0.0005 (8) | −0.0055 (8) |
C12 | 0.0205 (10) | 0.0339 (11) | 0.0357 (12) | −0.0081 (9) | −0.0062 (9) | 0.0021 (9) |
C13 | 0.0208 (9) | 0.0191 (9) | 0.0197 (9) | 0.0005 (7) | −0.0032 (7) | 0.0034 (7) |
Cl1—C3 | 1.742 (2) | C6—C7 | 1.527 (3) |
O1—C2 | 1.336 (2) | C6—H6A | 0.9700 |
O1—C1 | 1.389 (3) | C6—H6B | 0.9700 |
C1—H1A | 0.9600 | C7—C8 | 1.525 (3) |
C1—H1B | 0.9600 | C7—C9 | 1.530 (3) |
C1—H1C | 0.9600 | C8—H8A | 0.9600 |
N1—C3 | 1.307 (3) | C8—H8B | 0.9600 |
N1—C4 | 1.366 (2) | C8—H8C | 0.9600 |
N2—C3 | 1.313 (3) | C9—H9A | 0.9600 |
N2—C2 | 1.341 (3) | C9—H9B | 0.9600 |
N3—C2 | 1.326 (3) | C9—H9C | 0.9600 |
N3—C4 | 1.346 (3) | C10—C12 | 1.523 (3) |
N4—C4 | 1.329 (2) | C10—C11 | 1.525 (3) |
N4—C5 | 1.456 (2) | C10—C13 | 1.526 (3) |
N4—H4 | 0.82 (3) | C11—H11A | 0.9600 |
N5—C7 | 1.520 (2) | C11—H11B | 0.9600 |
N5—C10 | 1.525 (2) | C11—H11C | 0.9600 |
N5—H5A | 0.86 (2) | C12—H12A | 0.9600 |
N5—H5B | 0.85 (3) | C12—H12B | 0.9600 |
C5—C13 | 1.521 (3) | C12—H12C | 0.9600 |
C5—C6 | 1.522 (3) | C13—H13A | 0.9700 |
C5—H5 | 0.9800 | C13—H13B | 0.9700 |
C2—O1—C1 | 119.09 (17) | N5—C7—C6 | 108.24 (14) |
O1—C1—H1A | 109.5 | C8—C7—C6 | 111.90 (15) |
O1—C1—H1B | 109.5 | N5—C7—C9 | 105.65 (14) |
H1A—C1—H1B | 109.5 | C8—C7—C9 | 109.46 (16) |
O1—C1—H1C | 109.5 | C6—C7—C9 | 110.26 (15) |
H1A—C1—H1C | 109.5 | C7—C8—H8A | 109.5 |
H1B—C1—H1C | 109.5 | C7—C8—H8B | 109.5 |
C3—N1—C4 | 112.36 (17) | H8A—C8—H8B | 109.5 |
C3—N2—C2 | 111.51 (17) | C7—C8—H8C | 109.5 |
C2—N3—C4 | 113.51 (17) | H8A—C8—H8C | 109.5 |
C4—N4—C5 | 123.67 (17) | H8B—C8—H8C | 109.5 |
C4—N4—H4 | 115.7 (17) | C7—C9—H9A | 109.5 |
C5—N4—H4 | 120.6 (17) | C7—C9—H9B | 109.5 |
C7—N5—C10 | 119.56 (14) | H9A—C9—H9B | 109.5 |
C7—N5—H5A | 107.6 (14) | C7—C9—H9C | 109.5 |
C10—N5—H5A | 108.8 (14) | H9A—C9—H9C | 109.5 |
C7—N5—H5B | 105.8 (16) | H9B—C9—H9C | 109.5 |
C10—N5—H5B | 107.0 (16) | C12—C10—C11 | 109.14 (16) |
H5A—N5—H5B | 107 (2) | C12—C10—N5 | 105.87 (15) |
N3—C2—O1 | 119.45 (18) | C11—C10—N5 | 110.86 (15) |
N3—C2—N2 | 127.54 (18) | C12—C10—C13 | 110.33 (16) |
O1—C2—N2 | 113.02 (17) | C11—C10—C13 | 112.65 (15) |
N1—C3—N2 | 130.13 (18) | N5—C10—C13 | 107.78 (14) |
N1—C3—Cl1 | 115.52 (15) | C10—C11—H11A | 109.5 |
N2—C3—Cl1 | 114.34 (14) | C10—C11—H11B | 109.5 |
N4—C4—N3 | 118.80 (17) | H11A—C11—H11B | 109.5 |
N4—C4—N1 | 116.26 (18) | C10—C11—H11C | 109.5 |
N3—C4—N1 | 124.94 (17) | H11A—C11—H11C | 109.5 |
N4—C5—C13 | 112.27 (15) | H11B—C11—H11C | 109.5 |
N4—C5—C6 | 109.68 (15) | C10—C12—H12A | 109.5 |
C13—C5—C6 | 109.31 (15) | C10—C12—H12B | 109.5 |
N4—C5—H5 | 108.5 | H12A—C12—H12B | 109.5 |
C13—C5—H5 | 108.5 | C10—C12—H12C | 109.5 |
C6—C5—H5 | 108.5 | H12A—C12—H12C | 109.5 |
C5—C6—C7 | 112.37 (15) | H12B—C12—H12C | 109.5 |
C5—C6—H6A | 109.1 | C5—C13—C10 | 112.14 (15) |
C7—C6—H6A | 109.1 | C5—C13—H13A | 109.2 |
C5—C6—H6B | 109.1 | C10—C13—H13A | 109.2 |
C7—C6—H6B | 109.1 | C5—C13—H13B | 109.2 |
H6A—C6—H6B | 107.9 | C10—C13—H13B | 109.2 |
N5—C7—C8 | 111.14 (15) | H13A—C13—H13B | 107.9 |
C4—N3—C2—O1 | −178.66 (17) | C4—N4—C5—C6 | 136.65 (19) |
C4—N3—C2—N2 | 0.6 (3) | N4—C5—C6—C7 | −176.00 (15) |
C1—O1—C2—N3 | −1.4 (3) | C13—C5—C6—C7 | 60.5 (2) |
C1—O1—C2—N2 | 179.17 (18) | C10—N5—C7—C8 | −74.9 (2) |
C3—N2—C2—N3 | −0.1 (3) | C10—N5—C7—C6 | 48.4 (2) |
C3—N2—C2—O1 | 179.19 (17) | C10—N5—C7—C9 | 166.45 (15) |
C4—N1—C3—N2 | 1.5 (3) | C5—C6—C7—N5 | −52.0 (2) |
C4—N1—C3—Cl1 | −177.39 (13) | C5—C6—C7—C8 | 70.9 (2) |
C2—N2—C3—N1 | −1.1 (3) | C5—C6—C7—C9 | −167.06 (15) |
C2—N2—C3—Cl1 | 177.82 (14) | C7—N5—C10—C12 | −167.06 (16) |
C5—N4—C4—N3 | 7.1 (3) | C7—N5—C10—C11 | 74.7 (2) |
C5—N4—C4—N1 | −172.68 (17) | C7—N5—C10—C13 | −49.0 (2) |
C2—N3—C4—N4 | −179.88 (18) | N4—C5—C13—C10 | 176.70 (15) |
C2—N3—C4—N1 | −0.1 (3) | C6—C5—C13—C10 | −61.3 (2) |
C3—N1—C4—N4 | 178.98 (17) | C12—C10—C13—C5 | 168.49 (16) |
C3—N1—C4—N3 | −0.8 (3) | C11—C10—C13—C5 | −69.3 (2) |
C4—N4—C5—C13 | −101.6 (2) | N5—C10—C13—C5 | 53.34 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···Cl2i | 0.82 (3) | 2.45 (3) | 3.2639 (19) | 171 (2) |
N5—H5A···Cl2 | 0.86 (2) | 2.33 (2) | 3.1821 (17) | 173.2 (19) |
N5—H5B···Cl2ii | 0.85 (3) | 2.32 (3) | 3.1714 (18) | 177 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H23ClN5O+·Cl− |
Mr | 336.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 113 |
a, b, c (Å) | 7.7987 (16), 8.9425 (18), 24.472 (5) |
β (°) | 90.36 (3) |
V (Å3) | 1706.7 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.30 × 0.26 × 0.22 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.893, 0.920 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13533, 3338, 3184 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.100, 1.08 |
No. of reflections | 3338 |
No. of parameters | 207 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.73, −0.38 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···Cl2i | 0.82 (3) | 2.45 (3) | 3.2639 (19) | 171 (2) |
N5—H5A···Cl2 | 0.86 (2) | 2.33 (2) | 3.1821 (17) | 173.2 (19) |
N5—H5B···Cl2ii | 0.85 (3) | 2.32 (3) | 3.1714 (18) | 177 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2. |
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The title compound is an intermediate for the synthesis of hindered light stabilizers (Borzatta & Carrozza, 1991). Its derivatives have many applications in organic chemistry (Deng et al., 2006).
The triazine ring is essentially planar with an r.m.s. deviation from the mean plane of 0.0038 Å. The molecules are linked by intermolecular N—H···Cl hydrogen bonds (Table 1) forming zigzag chains.