2,4-Dichloro-6-[2-meth-oxy-4-(prop-2-en-1-yl)phen-oxy]-1,3,5-triazine.

The title compound, C(13)H(11)Cl(2)N(3)O(2), was obtained by the reaction of eugenol and cyanuric chloride. The dihedral angle between the benzene and triazine rings is 87.56 (4)°. Two C atoms of the allyl group are disordered over two sites in a 0.72 (2):0.28 (2) ratio.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ▶). For related structures, see: Ma et al.(2010a ▶, ▶). For agricultural applications of the title compound, see: Manning et al. (1987 ▶).

Experimental

Crystal data

C13H11Cl2N3O2

M = 312.15

Monoclinic,

a = 11.4771 (12) Å

b = 8.6050 (9) Å

c = 14.7189 (13) Å

β = 103.077 (1)°

V = 1415.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 298 K

0.42 × 0.35 × 0.33 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.830, T max = 0.862

6755 measured reflections

2499 independent reflections

1595 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.099

S = 1.02

2499 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042418/rn2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042418/rn2069Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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)