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organic compounds
4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India, cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and dDepartment of Printing, Manipal Institute of Technology, Manipal University, Manipal 576 104, India
*Correspondence e-mail: hkfun@usm.my
The 7H10N2O4S, comprises of two independent molecules (A and B) which differ in the orientation of the methylsulfonyl group [C—S—C—N = 157.98 (13)° in molecule A and 6.09 (18)° in molecule B]. In the molecules of type A are linked into chains along the a axis by intermolecular C—H⋯O hydrogen bonds. The B molecules are linked to these chains by C—H⋯O hydrogen bonds.
of the title compound, CRelated literature
For general background and applications of 4,6-dimethoxypyrimidin-2-yl derivatives, see: Xi et al. (2006); He et al. (2007
); Li et al. (2006
); Gerorge (1983
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009
).
Supporting information
https://doi.org/10.1107/S1600536810025067/ci5121sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025067/ci5121Isup2.hkl
Periodic acid (2.63 mmol, 600 mg) was dissolved in acetonitrile (6 ml) by stirring at room temperature for 1 h. To this solution, chromium trioxide (0.125 mmol, 12.5 mg) was added and stirred for 5 min to give a clear orange solution. H5IO6/CrO3 solution (1.7 ml) was added to a solution of 4,6-dimethoxy-2-methylmercaptopyrimidine (0.23 mmol) in ethyl acetate and was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated sodium sulphite and was loaded on to a silica column. The column was eluted with acetone to obtain 4,6-dimethoxy-2-methylsulfonylpyrimidine. Single crystals were recrystallized from an dichloromethane solution (yield: 87%, m.p. 402–405 K).
All H atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating-group model was applied for the methyl groups.
Compounds containing 4,6-dimethoxypyrimidin-2-yl moieties display excellent herbicidal activity (Xi et al., 2006). Most sulfonylurea herbicides and all pyrimidinylbenzoate herbicides (He et al., 2007), such as nicofulfuron, amidosulfuron, halopyrazosulfuron, ethoxysulfuron, pyriminobac-methyl and pyriftalid, possess 4,6-dimethoxypyrimidin-2-yl groups (Li et al., 2006), while sulfometuron-methyl, a kind of sulfonylurea, contains a 4,6-dimethylpyrimidin-2-yl group, which suggests that the two disubstituted pyrimidin- 2-yl groups possess high biological activity (Gerorge, 1983).
There are two molecules, A and B, in the
(Fig. 1) of the title compound. The molecules A and B differ in the orientation of the methylsulfonyl group [C7A—S1A—C1A—N1A = 157.98 (13)° and C7B—S1B—C1B—N2B = 6.09 (18)°]In the
the A molecules are linked into chains along a axis by intermolecular C3A—H3AA···O2A and C7A—H7AA···O4A hydrogen bonds. The B molecules are linked to these chains by intermolecular C5A—H5AC···O2B hydrogen bonds.For general background and applications of 4,6-dimethoxypyrimidin-2-yl derivatives, see: Xi et al. (2006); He et al. (2007); Li et al. (2006); Gerorge (1983).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C7H10N2O4S | Z = 4 |
Mr = 218.23 | F(000) = 456 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.349 (2) Å | Cell parameters from 8362 reflections |
b = 11.067 (3) Å | θ = 2.2–32.1° |
c = 11.438 (3) Å | µ = 0.32 mm−1 |
α = 108.457 (8)° | T = 296 K |
β = 92.774 (8)° | Plate, colourless |
γ = 98.504 (8)° | 0.38 × 0.30 × 0.08 mm |
V = 986.4 (4) Å3 |
Bruker APEXII DUO CCD area-detector diffractometer | 7063 independent reflections |
Radiation source: fine-focus sealed tube | 4866 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 32.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
Tmin = 0.889, Tmax = 0.974 | k = −16→16 |
29277 measured reflections | l = −17→16 |
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) = 0.156 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1962P] where P = (Fo2 + 2Fc2)/3 |
7063 reflections | (Δ/σ)max = 0.001 |
259 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
C7H10N2O4S | γ = 98.504 (8)° |
Mr = 218.23 | V = 986.4 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.349 (2) Å | Mo Kα radiation |
b = 11.067 (3) Å | µ = 0.32 mm−1 |
c = 11.438 (3) Å | T = 296 K |
α = 108.457 (8)° | 0.38 × 0.30 × 0.08 mm |
β = 92.774 (8)° |
Bruker APEXII DUO CCD area-detector diffractometer | 7063 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4866 reflections with I > 2σ(I) |
Tmin = 0.889, Tmax = 0.974 | Rint = 0.042 |
29277 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.50 e Å−3 |
7063 reflections | Δρmin = −0.50 e Å−3 |
259 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 | ||
S1A | −0.01034 (4) | 0.04422 (4) | 0.19330 (4) | 0.03856 (12) | |
O1A | −0.02361 (19) | 0.10070 (16) | 0.32304 (15) | 0.0632 (4) | |
O2A | −0.08995 (15) | 0.09457 (13) | 0.10934 (15) | 0.0518 (3) | |
O3A | 0.50597 (16) | 0.29863 (13) | 0.14202 (15) | 0.0528 (3) | |
O4A | 0.51835 (16) | −0.11116 (13) | 0.16945 (16) | 0.0543 (3) | |
N1A | 0.26662 (16) | 0.17382 (13) | 0.16027 (13) | 0.0362 (3) | |
N2A | 0.27464 (15) | −0.03547 (13) | 0.17789 (13) | 0.0364 (3) | |
C1A | 0.20400 (17) | 0.06224 (14) | 0.17287 (14) | 0.0334 (3) | |
C2A | 0.43408 (19) | −0.01755 (16) | 0.16718 (16) | 0.0386 (3) | |
C3A | 0.51867 (19) | 0.09495 (18) | 0.15559 (17) | 0.0435 (4) | |
H3AA | 0.6304 | 0.1068 | 0.1502 | 0.052* | |
C4A | 0.42742 (19) | 0.18858 (16) | 0.15246 (15) | 0.0378 (3) | |
C5A | 0.4131 (3) | 0.3951 (2) | 0.1326 (3) | 0.0608 (5) | |
H5AA | 0.4838 | 0.4653 | 0.1194 | 0.091* | |
H5AB | 0.3635 | 0.4268 | 0.2078 | 0.091* | |
H5AC | 0.3300 | 0.3577 | 0.0642 | 0.091* | |
C6A | 0.4289 (3) | −0.2300 (2) | 0.1768 (3) | 0.0630 (6) | |
H6AA | 0.5032 | −0.2872 | 0.1814 | 0.095* | |
H6AB | 0.3525 | −0.2704 | 0.1045 | 0.095* | |
H6AC | 0.3714 | −0.2116 | 0.2494 | 0.095* | |
C7A | −0.0758 (2) | −0.12239 (17) | 0.1485 (2) | 0.0476 (4) | |
H7AA | −0.1909 | −0.1400 | 0.1536 | 0.071* | |
H7AB | −0.0197 | −0.1571 | 0.2024 | 0.071* | |
H7AC | −0.0529 | −0.1618 | 0.0648 | 0.071* | |
S1B | 0.91824 (6) | 0.54889 (4) | 0.18573 (4) | 0.04122 (12) | |
O1B | 1.0732 (2) | 0.63051 (15) | 0.21079 (16) | 0.0655 (4) | |
O2B | 0.8041 (2) | 0.56321 (17) | 0.09628 (13) | 0.0639 (4) | |
O3B | 0.7212 (2) | 0.42513 (15) | 0.54172 (14) | 0.0673 (5) | |
O4B | 0.6688 (2) | 0.83263 (14) | 0.52687 (15) | 0.0629 (4) | |
N1B | 0.78624 (19) | 0.69578 (14) | 0.36974 (14) | 0.0437 (3) | |
N2B | 0.81160 (19) | 0.48548 (14) | 0.37722 (13) | 0.0414 (3) | |
C1B | 0.8263 (2) | 0.57971 (16) | 0.32927 (15) | 0.0382 (3) | |
C2B | 0.7173 (2) | 0.71868 (18) | 0.47615 (17) | 0.0471 (4) | |
C3B | 0.6896 (3) | 0.6287 (2) | 0.53590 (18) | 0.0574 (5) | |
H3BA | 0.6383 | 0.6454 | 0.6084 | 0.069* | |
C4B | 0.7415 (3) | 0.51237 (18) | 0.48331 (17) | 0.0479 (4) | |
C5B | 0.7711 (4) | 0.3023 (2) | 0.4853 (2) | 0.0658 (6) | |
H5BA | 0.7710 | 0.2564 | 0.5438 | 0.099* | |
H5BB | 0.8787 | 0.3163 | 0.4607 | 0.099* | |
H5BC | 0.6967 | 0.2525 | 0.4138 | 0.099* | |
C6B | 0.7263 (4) | 0.9364 (2) | 0.4804 (2) | 0.0717 (7) | |
H6BA | 0.7075 | 1.0168 | 0.5370 | 0.108* | |
H6BB | 0.6689 | 0.9210 | 0.4009 | 0.108* | |
H6BC | 0.8408 | 0.9406 | 0.4725 | 0.108* | |
C7B | 0.9425 (3) | 0.38667 (19) | 0.1441 (2) | 0.0596 (6) | |
H7BA | 0.9860 | 0.3620 | 0.0655 | 0.089* | |
H7BB | 0.8389 | 0.3332 | 0.1384 | 0.089* | |
H7BC | 1.0160 | 0.3758 | 0.2058 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.02471 (18) | 0.03529 (19) | 0.0583 (3) | 0.00757 (13) | 0.01261 (15) | 0.01667 (17) |
O1A | 0.0498 (8) | 0.0687 (9) | 0.0636 (9) | 0.0117 (7) | 0.0238 (7) | 0.0079 (7) |
O2A | 0.0291 (6) | 0.0482 (7) | 0.0888 (10) | 0.0116 (5) | 0.0074 (6) | 0.0351 (7) |
O3A | 0.0338 (6) | 0.0503 (7) | 0.0794 (10) | −0.0034 (5) | 0.0040 (6) | 0.0332 (7) |
O4A | 0.0313 (6) | 0.0516 (7) | 0.0890 (10) | 0.0153 (5) | 0.0114 (6) | 0.0311 (7) |
N1A | 0.0264 (6) | 0.0368 (6) | 0.0450 (7) | 0.0026 (5) | 0.0036 (5) | 0.0143 (5) |
N2A | 0.0255 (6) | 0.0385 (6) | 0.0472 (7) | 0.0077 (5) | 0.0063 (5) | 0.0156 (6) |
C1A | 0.0226 (6) | 0.0364 (7) | 0.0410 (8) | 0.0041 (5) | 0.0052 (5) | 0.0126 (6) |
C2A | 0.0265 (7) | 0.0440 (8) | 0.0473 (9) | 0.0093 (6) | 0.0055 (6) | 0.0159 (7) |
C3A | 0.0235 (7) | 0.0518 (9) | 0.0575 (10) | 0.0048 (6) | 0.0060 (6) | 0.0216 (8) |
C4A | 0.0283 (7) | 0.0419 (8) | 0.0433 (8) | 0.0003 (6) | 0.0034 (6) | 0.0167 (6) |
C5A | 0.0500 (11) | 0.0536 (11) | 0.0890 (16) | 0.0007 (9) | 0.0077 (10) | 0.0411 (11) |
C6A | 0.0476 (11) | 0.0511 (11) | 0.1001 (18) | 0.0169 (9) | 0.0138 (11) | 0.0339 (11) |
C7A | 0.0319 (8) | 0.0385 (8) | 0.0761 (13) | 0.0027 (6) | 0.0102 (8) | 0.0249 (8) |
S1B | 0.0485 (2) | 0.0379 (2) | 0.0431 (2) | 0.01011 (16) | 0.01501 (17) | 0.01859 (16) |
O1B | 0.0583 (9) | 0.0610 (9) | 0.0768 (10) | −0.0036 (7) | 0.0250 (8) | 0.0258 (8) |
O2B | 0.0830 (12) | 0.0751 (10) | 0.0444 (7) | 0.0300 (9) | 0.0083 (7) | 0.0269 (7) |
O3B | 0.1028 (14) | 0.0552 (8) | 0.0543 (8) | 0.0157 (8) | 0.0304 (8) | 0.0283 (7) |
O4B | 0.0800 (11) | 0.0481 (8) | 0.0605 (9) | 0.0220 (7) | 0.0250 (8) | 0.0102 (7) |
N1B | 0.0480 (8) | 0.0403 (7) | 0.0440 (8) | 0.0111 (6) | 0.0096 (6) | 0.0132 (6) |
N2B | 0.0465 (8) | 0.0401 (7) | 0.0396 (7) | 0.0060 (6) | 0.0089 (6) | 0.0160 (6) |
C1B | 0.0382 (8) | 0.0395 (8) | 0.0376 (8) | 0.0067 (6) | 0.0064 (6) | 0.0134 (6) |
C2B | 0.0506 (10) | 0.0433 (9) | 0.0442 (9) | 0.0100 (7) | 0.0103 (7) | 0.0084 (7) |
C3B | 0.0775 (15) | 0.0518 (11) | 0.0430 (10) | 0.0119 (10) | 0.0243 (9) | 0.0126 (8) |
C4B | 0.0593 (11) | 0.0450 (9) | 0.0394 (9) | 0.0040 (8) | 0.0115 (8) | 0.0151 (7) |
C5B | 0.0955 (19) | 0.0489 (11) | 0.0579 (13) | 0.0094 (11) | 0.0111 (12) | 0.0255 (10) |
C6B | 0.104 (2) | 0.0477 (11) | 0.0687 (14) | 0.0285 (12) | 0.0197 (13) | 0.0182 (10) |
C7B | 0.0803 (15) | 0.0423 (10) | 0.0653 (13) | 0.0231 (9) | 0.0347 (11) | 0.0206 (9) |
S1A—O1A | 1.4334 (16) | S1B—O1B | 1.4234 (16) |
S1A—O2A | 1.4356 (14) | S1B—O2B | 1.4260 (16) |
S1A—C7A | 1.7429 (18) | S1B—C7B | 1.751 (2) |
S1A—C1A | 1.8059 (15) | S1B—C1B | 1.8018 (17) |
O3A—C4A | 1.338 (2) | O3B—C4B | 1.333 (2) |
O3A—C5A | 1.436 (3) | O3B—C5B | 1.441 (3) |
O4A—C2A | 1.342 (2) | O4B—C2B | 1.342 (2) |
O4A—C6A | 1.443 (2) | O4B—C6B | 1.442 (3) |
N1A—C1A | 1.322 (2) | N1B—C1B | 1.320 (2) |
N1A—C4A | 1.339 (2) | N1B—C2B | 1.339 (2) |
N2A—C1A | 1.321 (2) | N2B—C1B | 1.317 (2) |
N2A—C2A | 1.334 (2) | N2B—C4B | 1.340 (2) |
C2A—C3A | 1.386 (2) | C2B—C3B | 1.375 (3) |
C3A—C4A | 1.382 (2) | C3B—C4B | 1.381 (3) |
C3A—H3AA | 0.93 | C3B—H3BA | 0.93 |
C5A—H5AA | 0.96 | C5B—H5BA | 0.96 |
C5A—H5AB | 0.96 | C5B—H5BB | 0.96 |
C5A—H5AC | 0.96 | C5B—H5BC | 0.96 |
C6A—H6AA | 0.96 | C6B—H6BA | 0.96 |
C6A—H6AB | 0.96 | C6B—H6BB | 0.96 |
C6A—H6AC | 0.96 | C6B—H6BC | 0.96 |
C7A—H7AA | 0.96 | C7B—H7BA | 0.96 |
C7A—H7AB | 0.96 | C7B—H7BB | 0.96 |
C7A—H7AC | 0.96 | C7B—H7BC | 0.96 |
O1A—S1A—O2A | 117.87 (10) | O1B—S1B—O2B | 117.30 (11) |
O1A—S1A—C7A | 109.37 (10) | O1B—S1B—C7B | 110.02 (12) |
O2A—S1A—C7A | 109.13 (9) | O2B—S1B—C7B | 109.13 (12) |
O1A—S1A—C1A | 107.07 (8) | O1B—S1B—C1B | 107.47 (9) |
O2A—S1A—C1A | 108.07 (8) | O2B—S1B—C1B | 107.25 (9) |
C7A—S1A—C1A | 104.49 (8) | C7B—S1B—C1B | 104.92 (9) |
C4A—O3A—C5A | 118.66 (14) | C4B—O3B—C5B | 118.20 (16) |
C2A—O4A—C6A | 117.66 (14) | C2B—O4B—C6B | 117.81 (17) |
C1A—N1A—C4A | 113.74 (14) | C1B—N1B—C2B | 113.47 (15) |
C1A—N2A—C2A | 113.88 (14) | C1B—N2B—C4B | 113.85 (15) |
N2A—C1A—N1A | 130.25 (14) | N2B—C1B—N1B | 130.63 (16) |
N2A—C1A—S1A | 115.13 (11) | N2B—C1B—S1B | 115.98 (12) |
N1A—C1A—S1A | 114.55 (11) | N1B—C1B—S1B | 113.38 (13) |
N2A—C2A—O4A | 119.16 (15) | N1B—C2B—O4B | 119.64 (18) |
N2A—C2A—C3A | 123.00 (15) | N1B—C2B—C3B | 122.83 (17) |
O4A—C2A—C3A | 117.83 (15) | O4B—C2B—C3B | 117.51 (17) |
C4A—C3A—C2A | 116.11 (15) | C2B—C3B—C4B | 116.88 (17) |
C4A—C3A—H3AA | 121.9 | C2B—C3B—H3BA | 121.6 |
C2A—C3A—H3AA | 121.9 | C4B—C3B—H3BA | 121.6 |
O3A—C4A—N1A | 119.54 (15) | O3B—C4B—N2B | 119.62 (17) |
O3A—C4A—C3A | 117.47 (15) | O3B—C4B—C3B | 118.09 (17) |
N1A—C4A—C3A | 122.99 (15) | N2B—C4B—C3B | 122.29 (17) |
O3A—C5A—H5AA | 109.5 | O3B—C5B—H5BA | 109.5 |
O3A—C5A—H5AB | 109.5 | O3B—C5B—H5BB | 109.5 |
H5AA—C5A—H5AB | 109.5 | H5BA—C5B—H5BB | 109.5 |
O3A—C5A—H5AC | 109.5 | O3B—C5B—H5BC | 109.5 |
H5AA—C5A—H5AC | 109.5 | H5BA—C5B—H5BC | 109.5 |
H5AB—C5A—H5AC | 109.5 | H5BB—C5B—H5BC | 109.5 |
O4A—C6A—H6AA | 109.5 | O4B—C6B—H6BA | 109.5 |
O4A—C6A—H6AB | 109.5 | O4B—C6B—H6BB | 109.5 |
H6AA—C6A—H6AB | 109.5 | H6BA—C6B—H6BB | 109.5 |
O4A—C6A—H6AC | 109.5 | O4B—C6B—H6BC | 109.5 |
H6AA—C6A—H6AC | 109.5 | H6BA—C6B—H6BC | 109.5 |
H6AB—C6A—H6AC | 109.5 | H6BB—C6B—H6BC | 109.5 |
S1A—C7A—H7AA | 109.5 | S1B—C7B—H7BA | 109.5 |
S1A—C7A—H7AB | 109.5 | S1B—C7B—H7BB | 109.5 |
H7AA—C7A—H7AB | 109.5 | H7BA—C7B—H7BB | 109.5 |
S1A—C7A—H7AC | 109.5 | S1B—C7B—H7BC | 109.5 |
H7AA—C7A—H7AC | 109.5 | H7BA—C7B—H7BC | 109.5 |
H7AB—C7A—H7AC | 109.5 | H7BB—C7B—H7BC | 109.5 |
C2A—N2A—C1A—N1A | −0.7 (3) | C4B—N2B—C1B—N1B | 1.4 (3) |
C2A—N2A—C1A—S1A | −177.62 (12) | C4B—N2B—C1B—S1B | −179.50 (13) |
C4A—N1A—C1A—N2A | −0.6 (3) | C2B—N1B—C1B—N2B | −1.2 (3) |
C4A—N1A—C1A—S1A | 176.33 (12) | C2B—N1B—C1B—S1B | 179.75 (13) |
O1A—S1A—C1A—N2A | 91.31 (14) | O1B—S1B—C1B—N2B | −110.99 (15) |
O2A—S1A—C1A—N2A | −140.77 (13) | O2B—S1B—C1B—N2B | 122.06 (15) |
C7A—S1A—C1A—N2A | −24.64 (15) | C7B—S1B—C1B—N2B | 6.09 (18) |
O1A—S1A—C1A—N1A | −86.07 (14) | O1B—S1B—C1B—N1B | 68.23 (16) |
O2A—S1A—C1A—N1A | 41.86 (14) | O2B—S1B—C1B—N1B | −58.72 (16) |
C7A—S1A—C1A—N1A | 157.98 (13) | C7B—S1B—C1B—N1B | −174.69 (15) |
C1A—N2A—C2A—O4A | −179.19 (16) | C1B—N1B—C2B—O4B | −179.21 (18) |
C1A—N2A—C2A—C3A | 1.8 (2) | C1B—N1B—C2B—C3B | −0.8 (3) |
C6A—O4A—C2A—N2A | 3.3 (3) | C6B—O4B—C2B—N1B | −14.0 (3) |
C6A—O4A—C2A—C3A | −177.70 (18) | C6B—O4B—C2B—C3B | 167.5 (2) |
N2A—C2A—C3A—C4A | −1.6 (3) | N1B—C2B—C3B—C4B | 2.1 (3) |
O4A—C2A—C3A—C4A | 179.42 (16) | O4B—C2B—C3B—C4B | −179.4 (2) |
C5A—O3A—C4A—N1A | −3.4 (3) | C5B—O3B—C4B—N2B | −2.2 (3) |
C5A—O3A—C4A—C3A | 177.06 (19) | C5B—O3B—C4B—C3B | 178.3 (2) |
C1A—N1A—C4A—O3A | −178.65 (15) | C1B—N2B—C4B—O3B | −179.31 (19) |
C1A—N1A—C4A—C3A | 0.8 (2) | C1B—N2B—C4B—C3B | 0.2 (3) |
C2A—C3A—C4A—O3A | 179.63 (16) | C2B—C3B—C4B—O3B | 177.7 (2) |
C2A—C3A—C4A—N1A | 0.1 (3) | C2B—C3B—C4B—N2B | −1.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3AA···O2Ai | 0.93 | 2.42 | 3.336 (2) | 169 |
C5A—H5AC···O2Bii | 0.96 | 2.55 | 3.303 (3) | 135 |
C7A—H7AA···O4Aiii | 0.96 | 2.50 | 3.426 (2) | 161 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C7H10N2O4S |
Mr | 218.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.349 (2), 11.067 (3), 11.438 (3) |
α, β, γ (°) | 108.457 (8), 92.774 (8), 98.504 (8) |
V (Å3) | 986.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.38 × 0.30 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.889, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29277, 7063, 4866 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.156, 1.08 |
No. of reflections | 7063 |
No. of parameters | 259 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.50 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3AA···O2Ai | 0.93 | 2.42 | 3.336 (2) | 169 |
C5A—H5AC···O2Bii | 0.96 | 2.55 | 3.303 (3) | 135 |
C7A—H7AA···O4Aiii | 0.96 | 2.50 | 3.426 (2) | 161 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |
Acknowledgements
HKF and CSY thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship. AMI is grateful to the Head of the Department of Chemistry and the Director, National Institute of Technology-Karnataka, India, for providing research facilities and for their encouragement. AMI is also thankful to USM for the partial sponsorship of his visit to the X-ray Crystallography Unit, School fo Physics, USM.
References
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Compounds containing 4,6-dimethoxypyrimidin-2-yl moieties display excellent herbicidal activity (Xi et al., 2006). Most sulfonylurea herbicides and all pyrimidinylbenzoate herbicides (He et al., 2007), such as nicofulfuron, amidosulfuron, halopyrazosulfuron, ethoxysulfuron, pyriminobac-methyl and pyriftalid, possess 4,6-dimethoxypyrimidin-2-yl groups (Li et al., 2006), while sulfometuron-methyl, a kind of sulfonylurea, contains a 4,6-dimethylpyrimidin-2-yl group, which suggests that the two disubstituted pyrimidin- 2-yl groups possess high biological activity (Gerorge, 1983).
There are two molecules, A and B, in the asymmetric unit (Fig. 1) of the title compound. The molecules A and B differ in the orientation of the methylsulfonyl group [C7A—S1A—C1A—N1A = 157.98 (13)° and C7B—S1B—C1B—N2B = 6.09 (18)°]
In the crystal structure, the A molecules are linked into chains along a axis by intermolecular C3A—H3AA···O2A and C7A—H7AA···O4A hydrogen bonds. The B molecules are linked to these chains by intermolecular C5A—H5AC···O2B hydrogen bonds.