Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022842/hg2230sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022842/hg2230Isup2.hkl |
CCDC reference: 651458
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (Wave) = 0.000 Å
- R factor = 0.032
- wR factor = 0.081
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 3670 Count of symmetry unique reflns 2187 Completeness (_total/calc) 167.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1483 Fraction of Friedel pairs measured 0.678 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 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
N,N'-dicyclohexylcarbodiimide (1.08 g,0.055 mol) dissolved in 10 ml of dichloromethane was added dropwise over 20 minutes to the vortex of a stirred solution of 2-(4,6-dimethoxypyrimidin-2-ylsulfanyl)benzoic acid (1.60 g,0.0055 mol) and 3-nitrobenzenamine (0.69 g,0.005 mol) in 30 ml dichloromethane at 273 K. Subsequently,the mixture was stirred 6 h more at room temperature and the resulting solution filtered and washed with dichloromethane. A solution of 50 ml of 10% sodium hydroxide was added and stirred 1 h more and extracted twice with dichloromethane. The separated dichloromethane layer, dried with magnesium sulfate, was evaporated in vacuo leaving a crude of white powder. These crystals were dissolved in ethanol and left to slowly evaporate at room temperature. After 5 d, single crystals suitable for X-ray analysis were obtained (m.p. 399–402 K).
All H atoms were placed in calculated positions with C—H = 0.93Å (aromatic) or C—H=0.96Å (methoxy) and N—H = 0.86 Å, and included in the final cycles of refinement in the riding-model approximation,with Uiso(H) = 1.2Ueq of the carrier atoms.
4,6-Dimethoxypyrimidines with a phenoxy substructure at the 2-position exhibit marked herbicidal activity (Nezu et al., 1996; Tamaru et al., 1997; Hudson et al., 2002). The title compound, (I,) has showed herbicidal activity against various grass and broadleaf weeds. The present X-ray crystal structure analysis was undertaken for understanding the relationship between structure and activity.
The bond lengths and angles in the pyrimidine moiety are close to those found in related compounds (Hall et al., 1999; Lin et al., 2001). Particularly, the angle N3—C14—N4 [125.68 (1)°] deviates significantly from the normal value. In the two benzene rings, the angles are close to 120° which are close to Caromatic—Caromatic—C = 120° (Park et al., 2005). There is an N—H..N intramolecular hydrogen bond between the proton on N1 and the pyrimidine nitrogen N3. Weak C—H···O, C—H···S and C—H···π interactions give rise to the formation of a 3-D network.
For related literature, see: Hall et al. (1999); Hudson et al. (2002); Lin et al. (2001); Nezu et al. (1996); Park et al. (2005); Tamaru et al. (1997).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Fig. 1. The molecular structure of (I), showing the hydrogen bond N1—H111—N3, with displacement ellipsoids drawn at the 50% probability level. |
C19H16N4O5S | F(000) = 856.00 |
Mr = 412.42 | Dx = 1.435 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: C -2yc | Cell parameters from 10239 reflections |
a = 18.3554 (9) Å | θ = 3.1–27.4° |
b = 12.3477 (6) Å | µ = 0.21 mm−1 |
c = 8.4209 (5) Å | T = 298 K |
β = 91.0467 (17)° | Chunk, colorless |
V = 1908.25 (17) Å3 | 0.46 × 0.42 × 0.38 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3417 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −21→23 |
Tmin = 0.904, Tmax = 0.923 | k = −15→15 |
8657 measured reflections | l = −10→10 |
3670 independent reflections |
Refinement on F2 | w = 1/[0.0009Fo2 + 1.0000σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.032 | (Δ/σ)max < 0.001 |
wR(F2) = 0.081 | Δρmax = 0.24 e Å−3 |
S = 1.02 | Δρmin = −0.26 e Å−3 |
3670 reflections | Extinction correction: Larson (1970) |
264 parameters | Extinction coefficient: 105 (15) |
0 restraints | Absolute structure: Flack (1983), 1523 Friedel pairs |
H-atom parameters constrained | Absolute structure parameter: 0.10 (5) |
C19H16N4O5S | V = 1908.25 (17) Å3 |
Mr = 412.42 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 18.3554 (9) Å | µ = 0.21 mm−1 |
b = 12.3477 (6) Å | T = 298 K |
c = 8.4209 (5) Å | 0.46 × 0.42 × 0.38 mm |
β = 91.0467 (17)° |
Rigaku R-AXIS RAPID diffractometer | 3670 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3417 reflections with F2 > 2σ(F2) |
Tmin = 0.904, Tmax = 0.923 | Rint = 0.022 |
8657 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.081 | Δρmax = 0.24 e Å−3 |
S = 1.02 | Δρmin = −0.26 e Å−3 |
3670 reflections | Absolute structure: Flack (1983), 1523 Friedel pairs |
264 parameters | Absolute structure parameter: 0.10 (5) |
0 restraints |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.38203 (3) | 0.89646 (3) | 1.00620 (6) | 0.03648 (10) | |
O1 | 0.20595 (9) | 0.69864 (12) | 0.8983 (2) | 0.0557 (4) | |
O2 | 0.50881 (17) | 0.37440 (19) | 0.5022 (4) | 0.1185 (10) | |
O3 | 0.52021 (13) | 0.54516 (18) | 0.4747 (3) | 0.1079 (9) | |
O4 | 0.46729 (6) | 0.83461 (12) | 0.45837 (14) | 0.0450 (3) | |
O5 | 0.64111 (8) | 0.86050 (14) | 0.86357 (17) | 0.0523 (4) | |
N1 | 0.31393 (9) | 0.71447 (12) | 0.76172 (19) | 0.0401 (4) | |
N2 | 0.48791 (12) | 0.46688 (18) | 0.5254 (2) | 0.0716 (7) | |
N3 | 0.43379 (8) | 0.86439 (12) | 0.71021 (16) | 0.0323 (3) | |
N4 | 0.51846 (9) | 0.88144 (12) | 0.92085 (18) | 0.0355 (3) | |
C1 | 0.30560 (10) | 0.94420 (14) | 0.8979 (2) | 0.0354 (4) | |
C2 | 0.29690 (11) | 1.05629 (16) | 0.8877 (2) | 0.0471 (5) | |
C3 | 0.23477 (13) | 1.09949 (17) | 0.8202 (3) | 0.0588 (6) | |
C4 | 0.18135 (12) | 1.0331 (2) | 0.7665 (3) | 0.0617 (7) | |
C5 | 0.18849 (12) | 0.92221 (19) | 0.7784 (2) | 0.0528 (5) | |
C6 | 0.25096 (10) | 0.87629 (13) | 0.8422 (2) | 0.0382 (4) | |
C7 | 0.25500 (10) | 0.75374 (14) | 0.8420 (2) | 0.0393 (4) | |
C8 | 0.33403 (10) | 0.60581 (13) | 0.7330 (2) | 0.0387 (4) | |
C9 | 0.29172 (12) | 0.51721 (16) | 0.7826 (2) | 0.0528 (6) | |
C10 | 0.31533 (16) | 0.41336 (18) | 0.7446 (3) | 0.0676 (7) | |
C11 | 0.37916 (14) | 0.39460 (17) | 0.6621 (3) | 0.0619 (7) | |
C12 | 0.41987 (12) | 0.48333 (16) | 0.6158 (2) | 0.0495 (5) | |
C13 | 0.39828 (12) | 0.58838 (14) | 0.6484 (2) | 0.0454 (5) | |
C14 | 0.45121 (9) | 0.88014 (12) | 0.8598 (2) | 0.0299 (3) | |
C15 | 0.48988 (10) | 0.85016 (13) | 0.60663 (19) | 0.0330 (4) | |
C16 | 0.56137 (10) | 0.84840 (14) | 0.6536 (2) | 0.0382 (4) | |
C17 | 0.57184 (10) | 0.86377 (13) | 0.8152 (2) | 0.0357 (4) | |
C18 | 0.52246 (12) | 0.8213 (2) | 0.3362 (2) | 0.0561 (6) | |
C19 | 0.65252 (12) | 0.8676 (2) | 1.0318 (2) | 0.0663 (7) | |
H2 | 0.3333 | 1.1019 | 0.9269 | 0.057* | |
H3 | 0.2295 | 1.1742 | 0.8114 | 0.071* | |
H4 | 0.1392 | 1.0625 | 0.7210 | 0.074* | |
H5 | 0.1507 | 0.8778 | 0.7429 | 0.063* | |
H9 | 0.2492 | 0.5278 | 0.8390 | 0.063* | |
H10 | 0.2875 | 0.3544 | 0.7756 | 0.081* | |
H11 | 0.3941 | 0.3245 | 0.6386 | 0.074* | |
H13 | 0.4260 | 0.6468 | 0.6147 | 0.055* | |
H16 | 0.5994 | 0.8379 | 0.5838 | 0.046* | |
H111 | 0.3426 | 0.7627 | 0.7237 | 0.048* | |
H181 | 0.5529 | 0.8845 | 0.3338 | 0.067* | |
H182 | 0.5518 | 0.7589 | 0.3603 | 0.067* | |
H183 | 0.4988 | 0.8119 | 0.2345 | 0.067* | |
H191 | 0.6268 | 0.8100 | 1.0829 | 0.080* | |
H192 | 0.6348 | 0.9360 | 1.0691 | 0.080* | |
H193 | 0.7036 | 0.8616 | 1.0564 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0305 (2) | 0.0476 (2) | 0.03144 (19) | 0.0019 (2) | 0.00422 (12) | −0.00328 (18) |
O1 | 0.0418 (8) | 0.0508 (7) | 0.0751 (10) | −0.0089 (7) | 0.0182 (7) | 0.0001 (6) |
O2 | 0.112 (2) | 0.0647 (11) | 0.181 (2) | 0.0312 (13) | 0.0587 (19) | −0.0176 (14) |
O3 | 0.0800 (16) | 0.0715 (12) | 0.174 (2) | 0.0058 (12) | 0.0649 (16) | −0.0083 (13) |
O4 | 0.0333 (7) | 0.0721 (8) | 0.0296 (5) | 0.0036 (6) | 0.0002 (5) | −0.0037 (5) |
O5 | 0.0267 (6) | 0.0909 (10) | 0.0390 (7) | 0.0035 (6) | −0.0050 (5) | −0.0005 (6) |
N1 | 0.0320 (8) | 0.0336 (7) | 0.0547 (9) | −0.0044 (6) | 0.0059 (6) | −0.0015 (5) |
N2 | 0.0611 (14) | 0.0560 (12) | 0.0982 (16) | 0.0114 (10) | 0.0141 (11) | −0.0125 (10) |
N3 | 0.0250 (7) | 0.0396 (6) | 0.0324 (7) | −0.0014 (5) | 0.0012 (5) | 0.0010 (5) |
N4 | 0.0283 (7) | 0.0449 (7) | 0.0333 (7) | 0.0014 (6) | −0.0004 (5) | −0.0003 (5) |
C1 | 0.0255 (8) | 0.0412 (8) | 0.0397 (9) | 0.0036 (7) | 0.0071 (6) | −0.0028 (6) |
C2 | 0.0387 (11) | 0.0394 (9) | 0.0633 (12) | −0.0017 (8) | 0.0074 (8) | −0.0041 (8) |
C3 | 0.0489 (13) | 0.0406 (10) | 0.0871 (17) | 0.0083 (9) | 0.0076 (11) | 0.0062 (10) |
C4 | 0.0385 (12) | 0.0606 (12) | 0.0859 (16) | 0.0141 (10) | −0.0037 (11) | 0.0098 (11) |
C5 | 0.0284 (10) | 0.0566 (10) | 0.0732 (13) | 0.0002 (9) | −0.0038 (8) | −0.0000 (9) |
C6 | 0.0287 (9) | 0.0410 (8) | 0.0449 (9) | 0.0014 (7) | 0.0041 (7) | −0.0006 (7) |
C7 | 0.0306 (9) | 0.0431 (8) | 0.0440 (9) | −0.0051 (7) | −0.0004 (6) | −0.0024 (7) |
C8 | 0.0365 (10) | 0.0346 (8) | 0.0446 (9) | −0.0032 (7) | −0.0074 (7) | −0.0017 (6) |
C9 | 0.0487 (13) | 0.0421 (10) | 0.0677 (13) | −0.0087 (9) | 0.0082 (9) | 0.0006 (8) |
C10 | 0.0665 (17) | 0.0381 (10) | 0.099 (2) | −0.0090 (11) | 0.0114 (13) | 0.0031 (10) |
C11 | 0.0656 (16) | 0.0355 (9) | 0.0845 (17) | 0.0023 (10) | −0.0022 (12) | −0.0056 (9) |
C12 | 0.0466 (12) | 0.0445 (10) | 0.0572 (11) | 0.0050 (9) | −0.0029 (9) | −0.0079 (8) |
C13 | 0.0419 (11) | 0.0378 (8) | 0.0565 (11) | −0.0013 (8) | −0.0001 (8) | −0.0040 (7) |
C14 | 0.0252 (8) | 0.0314 (7) | 0.0332 (7) | −0.0005 (6) | 0.0022 (5) | 0.0015 (5) |
C15 | 0.0302 (8) | 0.0388 (8) | 0.0299 (8) | 0.0009 (7) | 0.0008 (6) | 0.0032 (6) |
C16 | 0.0286 (8) | 0.0517 (9) | 0.0344 (8) | 0.0019 (7) | 0.0048 (6) | 0.0030 (7) |
C17 | 0.0244 (8) | 0.0441 (8) | 0.0386 (8) | 0.0006 (7) | −0.0011 (6) | 0.0035 (7) |
C18 | 0.0487 (12) | 0.0900 (15) | 0.0297 (9) | 0.0020 (11) | 0.0061 (8) | −0.0040 (9) |
C19 | 0.0338 (12) | 0.121 (2) | 0.0436 (11) | 0.0063 (12) | −0.0112 (8) | −0.0028 (12) |
S1—C1 | 1.7608 (18) | C8—C13 | 1.405 (2) |
S1—C14 | 1.7973 (17) | C9—C10 | 1.393 (3) |
O1—C7 | 1.231 (2) | C10—C11 | 1.393 (4) |
O2—N2 | 1.221 (3) | C11—C12 | 1.386 (3) |
O3—N2 | 1.216 (3) | C12—C13 | 1.385 (2) |
O4—C15 | 1.322 (2) | C15—C16 | 1.364 (2) |
O4—C18 | 1.466 (2) | C16—C17 | 1.384 (2) |
O5—C17 | 1.329 (2) | N1—H111 | 0.860 |
O5—C19 | 1.431 (2) | C2—H2 | 0.930 |
N1—C7 | 1.374 (2) | C3—H3 | 0.930 |
N1—C8 | 1.414 (2) | C4—H4 | 0.930 |
N2—C12 | 1.488 (3) | C5—H5 | 0.930 |
N3—C14 | 1.308 (2) | C9—H9 | 0.930 |
N3—C15 | 1.373 (2) | C10—H10 | 0.930 |
N4—C14 | 1.329 (2) | C11—H11 | 0.930 |
N4—C17 | 1.353 (2) | C13—H13 | 0.930 |
C1—C2 | 1.396 (2) | C16—H16 | 0.930 |
C1—C6 | 1.383 (2) | C18—H181 | 0.960 |
C2—C3 | 1.373 (3) | C18—H182 | 0.960 |
C3—C4 | 1.350 (3) | C18—H183 | 0.960 |
C4—C5 | 1.379 (3) | C19—H191 | 0.960 |
C5—C6 | 1.379 (2) | C19—H192 | 0.960 |
C6—C7 | 1.515 (2) | C19—H193 | 0.960 |
C8—C9 | 1.409 (2) | ||
C1—S1—C14 | 104.39 (8) | N3—C15—C16 | 123.14 (15) |
C15—O4—C18 | 118.05 (14) | C15—C16—C17 | 113.49 (16) |
C17—O5—C19 | 115.06 (15) | O5—C17—N4 | 120.25 (16) |
C7—N1—C8 | 129.00 (15) | O5—C17—C16 | 114.34 (16) |
O2—N2—O3 | 122.0 (2) | N4—C17—C16 | 125.41 (16) |
O2—N2—C12 | 118.6 (2) | C7—N1—H111 | 115.5 |
O3—N2—C12 | 119.4 (2) | C8—N1—H111 | 115.5 |
C14—N3—C15 | 117.24 (14) | C1—C2—H2 | 119.9 |
C14—N4—C17 | 114.99 (15) | C3—C2—H2 | 119.9 |
S1—C1—C2 | 116.94 (14) | C2—C3—H3 | 120.1 |
S1—C1—C6 | 122.61 (14) | C4—C3—H3 | 120.1 |
C2—C1—C6 | 119.94 (16) | C3—C4—H4 | 119.6 |
C1—C2—C3 | 120.26 (18) | C5—C4—H4 | 119.6 |
C2—C3—C4 | 119.7 (2) | C4—C5—H5 | 119.5 |
C3—C4—C5 | 120.8 (2) | C6—C5—H5 | 119.5 |
C4—C5—C6 | 120.9 (2) | C8—C9—H9 | 120.9 |
C1—C6—C5 | 118.40 (17) | C10—C9—H9 | 120.9 |
C1—C6—C7 | 124.81 (16) | C9—C10—H10 | 118.8 |
C5—C6—C7 | 116.78 (16) | C11—C10—H10 | 118.8 |
O1—C7—N1 | 125.63 (17) | C10—C11—H11 | 120.9 |
O1—C7—C6 | 121.04 (16) | C12—C11—H11 | 120.9 |
N1—C7—C6 | 113.08 (15) | C8—C13—H13 | 120.3 |
N1—C8—C9 | 122.62 (17) | C12—C13—H13 | 120.3 |
N1—C8—C13 | 117.14 (15) | C15—C16—H16 | 123.3 |
C9—C8—C13 | 120.22 (17) | C17—C16—H16 | 123.3 |
C8—C9—C10 | 118.1 (2) | O4—C18—H181 | 109.5 |
C9—C10—C11 | 122.4 (2) | O4—C18—H182 | 109.5 |
C10—C11—C12 | 118.1 (2) | O4—C18—H183 | 109.5 |
N2—C12—C11 | 119.84 (19) | H181—C18—H182 | 109.5 |
N2—C12—C13 | 118.36 (18) | H181—C18—H183 | 109.5 |
C11—C12—C13 | 121.8 (2) | H182—C18—H183 | 109.5 |
C8—C13—C12 | 119.32 (18) | O5—C19—H191 | 109.5 |
S1—C14—N3 | 120.91 (12) | O5—C19—H192 | 109.5 |
S1—C14—N4 | 113.35 (12) | O5—C19—H193 | 109.5 |
N3—C14—N4 | 125.68 (15) | H191—C19—H192 | 109.5 |
O4—C15—N3 | 113.12 (15) | H191—C19—H193 | 109.5 |
O4—C15—C16 | 123.71 (16) | H192—C19—H193 | 109.5 |
C1—S1—C14—N3 | −24.72 (16) | C2—C1—C6—C5 | −0.5 (2) |
C1—S1—C14—N4 | 157.85 (12) | C2—C1—C6—C7 | 178.00 (17) |
C14—S1—C1—C2 | −92.52 (15) | C6—C1—C2—C3 | −1.1 (3) |
C14—S1—C1—C6 | 95.79 (16) | C1—C2—C3—C4 | 1.4 (3) |
C18—O4—C15—N3 | 178.38 (17) | C2—C3—C4—C5 | −0.2 (3) |
C18—O4—C15—C16 | −3.9 (2) | C3—C4—C5—C6 | −1.4 (3) |
C19—O5—C17—N4 | 5.0 (2) | C4—C5—C6—C1 | 1.7 (3) |
C19—O5—C17—C16 | −175.2 (2) | C4—C5—C6—C7 | −176.9 (2) |
C7—N1—C8—C9 | 2.2 (3) | C1—C6—C7—O1 | 128.8 (2) |
C7—N1—C8—C13 | −179.17 (18) | C1—C6—C7—N1 | −56.6 (2) |
C8—N1—C7—O1 | −3.7 (3) | C5—C6—C7—O1 | −52.7 (2) |
C8—N1—C7—C6 | −177.95 (16) | C5—C6—C7—N1 | 121.85 (19) |
O2—N2—C12—C11 | −4.4 (3) | N1—C8—C9—C10 | 178.3 (2) |
O2—N2—C12—C13 | 176.9 (2) | N1—C8—C13—C12 | −179.31 (18) |
O3—N2—C12—C11 | 174.3 (2) | C9—C8—C13—C12 | −0.6 (3) |
O3—N2—C12—C13 | −4.4 (3) | C13—C8—C9—C10 | −0.3 (3) |
C14—N3—C15—O4 | 179.89 (15) | C8—C9—C10—C11 | 0.9 (3) |
C14—N3—C15—C16 | 2.1 (2) | C9—C10—C11—C12 | −0.4 (4) |
C15—N3—C14—S1 | −178.51 (12) | C10—C11—C12—N2 | −179.2 (2) |
C15—N3—C14—N4 | −1.4 (2) | C10—C11—C12—C13 | −0.5 (3) |
C14—N4—C17—O5 | −178.28 (16) | N2—C12—C13—C8 | 179.73 (19) |
C14—N4—C17—C16 | 2.0 (2) | C11—C12—C13—C8 | 1.1 (3) |
C17—N4—C14—S1 | 176.74 (12) | O4—C15—C16—C17 | −178.33 (16) |
C17—N4—C14—N3 | −0.5 (2) | N3—C15—C16—C17 | −0.8 (2) |
S1—C1—C2—C3 | −172.99 (18) | C15—C16—C17—O5 | 178.93 (16) |
S1—C1—C6—C5 | 170.98 (16) | C15—C16—C17—N4 | −1.4 (2) |
S1—C1—C6—C7 | −10.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C19H16N4O5S |
Mr | 412.42 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 298 |
a, b, c (Å) | 18.3554 (9), 12.3477 (6), 8.4209 (5) |
β (°) | 91.0467 (17) |
V (Å3) | 1908.25 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.46 × 0.42 × 0.38 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.904, 0.923 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 8657, 3670, 3417 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.081, 1.02 |
No. of reflections | 3670 |
No. of parameters | 264 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.26 |
Absolute structure | Flack (1983), 1523 Friedel pairs |
Absolute structure parameter | 0.10 (5) |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure.
D—H···A | D—H | H···A | D···A | D—H···A |
N(1)—H(111)···N(3) | 0.860 | 2.098 | 2.914 (2) | 158.2 |
4,6-Dimethoxypyrimidines with a phenoxy substructure at the 2-position exhibit marked herbicidal activity (Nezu et al., 1996; Tamaru et al., 1997; Hudson et al., 2002). The title compound, (I,) has showed herbicidal activity against various grass and broadleaf weeds. The present X-ray crystal structure analysis was undertaken for understanding the relationship between structure and activity.
The bond lengths and angles in the pyrimidine moiety are close to those found in related compounds (Hall et al., 1999; Lin et al., 2001). Particularly, the angle N3—C14—N4 [125.68 (1)°] deviates significantly from the normal value. In the two benzene rings, the angles are close to 120° which are close to Caromatic—Caromatic—C = 120° (Park et al., 2005). There is an N—H..N intramolecular hydrogen bond between the proton on N1 and the pyrimidine nitrogen N3. Weak C—H···O, C—H···S and C—H···π interactions give rise to the formation of a 3-D network.