

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810042418/rn2069sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810042418/rn2069Isup2.hkl |
CCDC reference: 773009
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 3 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 9.00 Perc. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 34.30 Deg. C12' -C11 -C12 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 35.20 Deg. H11A -C11 -H11C 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 35.40 Deg. H11B -C11 -H11D 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 37.00 Deg. C11 -C12 -H11C 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
492 mg eugenol (3 mmol) was dissolved in 1.2 g 10% sodium hydroxide (3 mmol) in a 100 mL round-bottom flask and the water was then removed in vacuo. Added 30 ml acetonitrile into the flask in an ice bath and after stirring 10 min cyanuric chloride (3 mmol) was added and kept stirred for 2 h at 278 K. The reaction mixture was filtered and solvent was evaporated under vacuum to dryness. The solid mass was dissolved in EtOAc, washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4, concentrated and purified with column chromatography to afford the crude product. White crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in n-hexane/ethyl acetate (1:1 V/V) at room temperature.
The atoms C12 and C13 were found to be disordered over two sites, and the ratio of the occupancy factors refined to 0.718 (7):0.282 (7) and 0.718 (7):0.282 (7) for atoms C12: C12' and C13: C13' respectively.The positions of all H atoms were determined geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(methyl H) = 1.5Ueq(C) and 1.2Ueq for other H atoms.
In this paper, we used the Williamson reaction (Dermer, 1934) to form the title compound, (I), which was synthesized by the reaction of eugenol, sodium hydroxide and cyanuric chloride at 278 K. We have previously reported three compounds of this type [Ma et al.(2010a, 2010b and 2010c)]. In (I)(Fig.1), the dihedral angle between the benzene ring C4—C9 and the triazine ring C2N3C3N1C1N2 is 87.56 (4)°. There are no significantly short intermolecular contacts in the crystal lattice.
For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For related structures, see: Ma et al.(2010a,b,c). For the agricultural applications of the title compound, see: Manning et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of (I), with atom labels and displacement ellipsoids drawn at the 30% probability level.The disordered atoms C12 and C13 of the allyl group are the major component. |
C13H11Cl2N3O2 | Dx = 1.464 Mg m−3 |
Mr = 312.15 | Melting point = 385–386 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4771 (12) Å | Cell parameters from 2205 reflections |
b = 8.6050 (9) Å | θ = 2.8–25.7° |
c = 14.7189 (13) Å | µ = 0.46 mm−1 |
β = 103.077 (1)° | T = 298 K |
V = 1415.9 (2) Å3 | Monoclinic, colourless |
Z = 4 | 0.42 × 0.35 × 0.33 mm |
F(000) = 640 |
Siemens SMART CCD area-detector diffractometer | 2499 independent reflections |
Radiation source: fine-focus sealed tube | 1595 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
phi and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.830, Tmax = 0.862 | k = −10→7 |
6755 measured reflections | l = −17→17 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0303P)2 + 0.7779P] where P = (Fo2 + 2Fc2)/3 |
2499 reflections | (Δ/σ)max = 0.001 |
201 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C13H11Cl2N3O2 | V = 1415.9 (2) Å3 |
Mr = 312.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4771 (12) Å | µ = 0.46 mm−1 |
b = 8.6050 (9) Å | T = 298 K |
c = 14.7189 (13) Å | 0.42 × 0.35 × 0.33 mm |
β = 103.077 (1)° |
Siemens SMART CCD area-detector diffractometer | 2499 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1595 reflections with I > 2σ(I) |
Tmin = 0.830, Tmax = 0.862 | Rint = 0.027 |
6755 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
2499 reflections | Δρmin = −0.23 e Å−3 |
201 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 | Occ. (<1) | |
Cl1 | 0.23031 (7) | 0.11286 (10) | 0.56145 (6) | 0.0754 (3) | |
Cl2 | 0.08975 (7) | 0.41854 (15) | 0.81780 (6) | 0.1061 (4) | |
N1 | 0.29775 (19) | 0.4567 (3) | 0.78327 (14) | 0.0541 (6) | |
N2 | 0.36101 (18) | 0.3198 (2) | 0.66250 (14) | 0.0459 (5) | |
N3 | 0.16967 (19) | 0.2701 (3) | 0.69226 (16) | 0.0621 (7) | |
O1 | 0.47642 (15) | 0.5029 (2) | 0.75543 (11) | 0.0524 (5) | |
O2 | 0.47302 (16) | 0.6829 (2) | 0.60769 (12) | 0.0583 (5) | |
C1 | 0.3757 (2) | 0.4227 (3) | 0.73157 (17) | 0.0450 (6) | |
C2 | 0.2573 (2) | 0.2488 (3) | 0.64855 (18) | 0.0525 (7) | |
C3 | 0.1983 (2) | 0.3770 (4) | 0.7582 (2) | 0.0613 (8) | |
C4 | 0.5660 (2) | 0.4821 (3) | 0.70437 (17) | 0.0439 (6) | |
C5 | 0.5664 (2) | 0.5829 (3) | 0.63087 (17) | 0.0433 (6) | |
C6 | 0.6619 (2) | 0.5747 (3) | 0.58824 (17) | 0.0486 (7) | |
H6 | 0.6644 | 0.6411 | 0.5389 | 0.058* | |
C7 | 0.7537 (2) | 0.4693 (3) | 0.61776 (18) | 0.0499 (7) | |
C8 | 0.7481 (2) | 0.3691 (3) | 0.6892 (2) | 0.0567 (7) | |
H8 | 0.8082 | 0.2958 | 0.7082 | 0.068* | |
C9 | 0.6542 (2) | 0.3762 (3) | 0.73313 (19) | 0.0543 (7) | |
H9 | 0.6513 | 0.3090 | 0.7820 | 0.065* | |
C10 | 0.4713 (3) | 0.7868 (3) | 0.5320 (2) | 0.0654 (8) | |
H10A | 0.5382 | 0.8565 | 0.5478 | 0.098* | |
H10B | 0.3983 | 0.8456 | 0.5198 | 0.098* | |
H10C | 0.4763 | 0.7285 | 0.4774 | 0.098* | |
C11 | 0.8576 (2) | 0.4640 (4) | 0.5703 (2) | 0.0653 (8) | |
H11A | 0.8779 | 0.5693 | 0.5563 | 0.078* | 0.72 (2) |
H11B | 0.9265 | 0.4199 | 0.6131 | 0.078* | 0.72 (2) |
H11C | 0.8464 | 0.5438 | 0.5226 | 0.078* | 0.28 (2) |
H11D | 0.9307 | 0.4883 | 0.6157 | 0.078* | 0.28 (2) |
C12 | 0.8333 (7) | 0.3729 (13) | 0.4838 (7) | 0.066 (2) | 0.72 (2) |
H12 | 0.7661 | 0.3994 | 0.4382 | 0.079* | 0.72 (2) |
C13 | 0.8975 (13) | 0.2594 (16) | 0.4660 (11) | 0.086 (3) | 0.72 (2) |
H13A | 0.9654 | 0.2292 | 0.5099 | 0.103* | 0.72 (2) |
H13B | 0.8759 | 0.2074 | 0.4093 | 0.103* | 0.72 (2) |
C12' | 0.876 (2) | 0.317 (2) | 0.527 (2) | 0.067 (6) | 0.28 (2) |
H12' | 0.8899 | 0.2272 | 0.5634 | 0.080* | 0.28 (2) |
C13' | 0.873 (3) | 0.310 (5) | 0.433 (2) | 0.082 (8) | 0.28 (2) |
H13C | 0.8587 | 0.3992 | 0.3970 | 0.099* | 0.28 (2) |
H13D | 0.8844 | 0.2152 | 0.4060 | 0.099* | 0.28 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0806 (5) | 0.0678 (5) | 0.0734 (5) | −0.0163 (4) | 0.0081 (4) | −0.0086 (4) |
Cl2 | 0.0585 (5) | 0.1906 (12) | 0.0795 (6) | −0.0079 (6) | 0.0370 (4) | −0.0104 (7) |
N1 | 0.0501 (13) | 0.0681 (16) | 0.0488 (13) | 0.0005 (12) | 0.0208 (11) | 0.0046 (12) |
N2 | 0.0491 (13) | 0.0447 (13) | 0.0449 (13) | −0.0015 (11) | 0.0129 (10) | 0.0040 (11) |
N3 | 0.0480 (13) | 0.0831 (19) | 0.0547 (15) | −0.0086 (13) | 0.0105 (11) | 0.0101 (14) |
O1 | 0.0533 (11) | 0.0569 (12) | 0.0531 (11) | −0.0097 (10) | 0.0246 (9) | −0.0077 (9) |
O2 | 0.0602 (11) | 0.0621 (12) | 0.0580 (12) | 0.0142 (10) | 0.0244 (9) | 0.0081 (10) |
C1 | 0.0452 (15) | 0.0491 (17) | 0.0422 (15) | 0.0015 (13) | 0.0127 (12) | 0.0103 (13) |
C2 | 0.0545 (16) | 0.0548 (18) | 0.0453 (15) | −0.0022 (15) | 0.0052 (13) | 0.0124 (13) |
C3 | 0.0517 (17) | 0.086 (2) | 0.0493 (17) | 0.0026 (17) | 0.0182 (14) | 0.0151 (17) |
C4 | 0.0440 (14) | 0.0464 (16) | 0.0439 (15) | −0.0098 (13) | 0.0155 (12) | −0.0053 (13) |
C5 | 0.0459 (14) | 0.0401 (15) | 0.0452 (15) | −0.0030 (12) | 0.0133 (11) | −0.0048 (13) |
C6 | 0.0520 (15) | 0.0490 (17) | 0.0481 (15) | −0.0064 (14) | 0.0177 (12) | 0.0004 (13) |
C7 | 0.0448 (15) | 0.0508 (17) | 0.0573 (17) | −0.0077 (14) | 0.0181 (13) | −0.0059 (14) |
C8 | 0.0484 (15) | 0.0515 (18) | 0.0705 (19) | 0.0048 (14) | 0.0142 (14) | 0.0019 (15) |
C9 | 0.0589 (17) | 0.0510 (17) | 0.0547 (17) | −0.0030 (15) | 0.0165 (14) | 0.0066 (14) |
C10 | 0.0724 (19) | 0.060 (2) | 0.0636 (19) | 0.0131 (17) | 0.0160 (15) | 0.0119 (17) |
C11 | 0.0523 (17) | 0.071 (2) | 0.080 (2) | −0.0070 (16) | 0.0292 (16) | −0.0036 (18) |
C12 | 0.051 (3) | 0.090 (5) | 0.064 (4) | 0.000 (3) | 0.027 (3) | 0.004 (4) |
C13 | 0.074 (6) | 0.086 (8) | 0.108 (11) | −0.012 (5) | 0.044 (6) | −0.021 (6) |
C12' | 0.068 (11) | 0.068 (10) | 0.078 (15) | 0.013 (8) | 0.043 (11) | 0.010 (9) |
C13' | 0.074 (15) | 0.10 (2) | 0.081 (19) | −0.010 (14) | 0.036 (13) | 0.007 (12) |
Cl1—C2 | 1.711 (3) | C8—H8 | 0.9300 |
Cl2—C3 | 1.715 (3) | C9—H9 | 0.9300 |
N1—C3 | 1.312 (3) | C10—H10A | 0.9600 |
N1—C1 | 1.332 (3) | C10—H10B | 0.9600 |
N2—C2 | 1.312 (3) | C10—H10C | 0.9600 |
N2—C1 | 1.330 (3) | C11—C12' | 1.451 (18) |
N3—C3 | 1.323 (4) | C11—C12 | 1.466 (7) |
N3—C2 | 1.324 (3) | C11—H11A | 0.9700 |
O1—C1 | 1.324 (3) | C11—H11B | 0.9700 |
O1—C4 | 1.416 (3) | C11—H11C | 0.9700 |
O2—C5 | 1.356 (3) | C11—H11D | 0.9700 |
O2—C10 | 1.425 (3) | C12—C13 | 1.29 (2) |
C4—C9 | 1.356 (4) | C12—H12 | 0.9300 |
C4—C5 | 1.387 (3) | C13—H13A | 0.9300 |
C5—C6 | 1.382 (3) | C13—H13B | 0.9300 |
C6—C7 | 1.384 (3) | C12'—C13' | 1.38 (5) |
C6—H6 | 0.9300 | C12'—H12' | 0.9300 |
C7—C8 | 1.372 (4) | C13'—H13C | 0.9300 |
C7—C11 | 1.513 (3) | C13'—H13D | 0.9300 |
C8—C9 | 1.378 (3) | ||
C3—N1—C1 | 112.3 (2) | H10B—C10—H10C | 109.5 |
C2—N2—C1 | 112.5 (2) | C12'—C11—C12 | 34.3 (9) |
C3—N3—C2 | 111.3 (2) | C12'—C11—C7 | 115.8 (6) |
C1—O1—C4 | 119.25 (19) | C12—C11—C7 | 113.7 (3) |
C5—O2—C10 | 117.7 (2) | C12'—C11—H11A | 131.1 |
O1—C1—N2 | 120.1 (2) | C12—C11—H11A | 108.8 |
O1—C1—N1 | 113.1 (2) | C7—C11—H11A | 108.8 |
N2—C1—N1 | 126.7 (2) | C12'—C11—H11B | 76.4 |
N2—C2—N3 | 128.4 (3) | C12—C11—H11B | 108.8 |
N2—C2—Cl1 | 116.1 (2) | C7—C11—H11B | 108.8 |
N3—C2—Cl1 | 115.5 (2) | H11A—C11—H11B | 107.7 |
N1—C3—N3 | 128.7 (3) | C12'—C11—H11C | 108.1 |
N1—C3—Cl2 | 115.7 (2) | C12—C11—H11C | 77.4 |
N3—C3—Cl2 | 115.6 (2) | C7—C11—H11C | 108.9 |
C9—C4—C5 | 122.0 (2) | H11A—C11—H11C | 35.2 |
C9—C4—O1 | 120.0 (2) | H11B—C11—H11C | 134.6 |
C5—C4—O1 | 117.7 (2) | C12'—C11—H11D | 107.5 |
O2—C5—C6 | 125.5 (2) | C12—C11—H11D | 132.7 |
O2—C5—C4 | 116.8 (2) | C7—C11—H11D | 108.9 |
C6—C5—C4 | 117.7 (2) | H11A—C11—H11D | 74.5 |
C5—C6—C7 | 121.1 (2) | H11B—C11—H11D | 35.4 |
C5—C6—H6 | 119.4 | H11C—C11—H11D | 107.4 |
C7—C6—H6 | 119.4 | C13—C12—C11 | 125.3 (14) |
C8—C7—C6 | 119.2 (2) | C13—C12—H11C | 140.6 |
C8—C7—C11 | 120.9 (3) | C11—C12—H11C | 37.0 |
C6—C7—C11 | 119.9 (3) | C13—C12—H12 | 117.4 |
C7—C8—C9 | 120.6 (3) | C11—C12—H12 | 117.4 |
C7—C8—H8 | 119.7 | H11C—C12—H12 | 91.6 |
C9—C8—H8 | 119.7 | C12—C13—H13A | 120.0 |
C4—C9—C8 | 119.4 (3) | C12—C13—H13B | 120.0 |
C4—C9—H9 | 120.3 | H13A—C13—H13B | 120.0 |
C8—C9—H9 | 120.3 | C13'—C12'—C11 | 120 (3) |
O2—C10—H10A | 109.5 | C13'—C12'—H12' | 119.9 |
O2—C10—H10B | 109.5 | C11—C12'—H12' | 119.9 |
H10A—C10—H10B | 109.5 | C12'—C13'—H13C | 120.0 |
O2—C10—H10C | 109.5 | C12'—C13'—H13D | 120.0 |
H10A—C10—H10C | 109.5 | H13C—C13'—H13D | 120.0 |
C4—O1—C1—N2 | 2.3 (3) | C9—C4—C5—C6 | −1.4 (4) |
C4—O1—C1—N1 | −178.1 (2) | O1—C4—C5—C6 | 172.4 (2) |
C2—N2—C1—O1 | 179.1 (2) | O2—C5—C6—C7 | 179.3 (2) |
C2—N2—C1—N1 | −0.5 (4) | C4—C5—C6—C7 | 0.2 (4) |
C3—N1—C1—O1 | 179.5 (2) | C5—C6—C7—C8 | 1.5 (4) |
C3—N1—C1—N2 | −0.9 (4) | C5—C6—C7—C11 | −179.5 (2) |
C1—N2—C2—N3 | 1.6 (4) | C6—C7—C8—C9 | −2.0 (4) |
C1—N2—C2—Cl1 | −179.54 (18) | C11—C7—C8—C9 | 179.0 (3) |
C3—N3—C2—N2 | −1.0 (4) | C5—C4—C9—C8 | 0.9 (4) |
C3—N3—C2—Cl1 | −180.0 (2) | O1—C4—C9—C8 | −172.7 (2) |
C1—N1—C3—N3 | 1.5 (4) | C7—C8—C9—C4 | 0.8 (4) |
C1—N1—C3—Cl2 | −177.49 (19) | C8—C7—C11—C12' | 58.8 (16) |
C2—N3—C3—N1 | −0.7 (4) | C6—C7—C11—C12' | −120.3 (16) |
C2—N3—C3—Cl2 | 178.3 (2) | C8—C7—C11—C12 | 96.6 (7) |
C1—O1—C4—C9 | −92.5 (3) | C6—C7—C11—C12 | −82.5 (7) |
C1—O1—C4—C5 | 93.6 (3) | C12'—C11—C12—C13 | −23.9 (13) |
C10—O2—C5—C6 | 1.2 (4) | C7—C11—C12—C13 | −125.3 (10) |
C10—O2—C5—C4 | −179.6 (2) | C12—C11—C12'—C13' | 26 (2) |
C9—C4—C5—O2 | 179.4 (2) | C7—C11—C12'—C13' | 121 (2) |
O1—C4—C5—O2 | −6.8 (3) |
Experimental details
Crystal data | |
Chemical formula | C13H11Cl2N3O2 |
Mr | 312.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 11.4771 (12), 8.6050 (9), 14.7189 (13) |
β (°) | 103.077 (1) |
V (Å3) | 1415.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.42 × 0.35 × 0.33 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.830, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6755, 2499, 1595 |
Rint | 0.027 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.099, 1.02 |
No. of reflections | 2499 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
In this paper, we used the Williamson reaction (Dermer, 1934) to form the title compound, (I), which was synthesized by the reaction of eugenol, sodium hydroxide and cyanuric chloride at 278 K. We have previously reported three compounds of this type [Ma et al.(2010a, 2010b and 2010c)]. In (I)(Fig.1), the dihedral angle between the benzene ring C4—C9 and the triazine ring C2N3C3N1C1N2 is 87.56 (4)°. There are no significantly short intermolecular contacts in the crystal lattice.