organic compounds
Methyl 2-{[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonylmethyl}benzoate
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
*Correspondence e-mail: fangshi.li@njut.edu.cn
In the title compound, C16H18N4O7S, a synthetic sulfonylurea herbicide, there are intramolecular N—H⋯N and C—H⋯O hydrogen bonds. Intermolecular N—H⋯O and C—H⋯O hydrogen bonds form centrosymmetric dimers. The dihedral angle between the two rings is 50.00 (15)°.
Related literature
For related literature, see: Kong et al. (1990); Lee et al. (2002); Sabadie (1996).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97.
Supporting information
10.1107/S1600536808005011/cf2185sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808005011/cf2185Isup2.hkl
The title compound, (I), was prepared according to the literature method (Kong et al., 1990).
Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.2 g) in ethyl acetate (25 ml) and evaporating the solvent slowly at room temperature for about 15 d.
All H atoms were positioned geometrically with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and were and included in the
in a riding model approximation, with Uiso(H) = 1.2 or 1.5Ueq(N,C).Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).C16H18N4O7S | F(000) = 1712 |
Mr = 410.41 | Dx = 1.505 Mg m−3 |
Monoclinic, C2/c | Melting point = 450–451 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 33.831 (7) Å | Cell parameters from 25 reflections |
b = 6.9020 (14) Å | θ = 10–13° |
c = 16.021 (3) Å | µ = 0.23 mm−1 |
β = 104.48 (3)° | T = 298 K |
V = 3622.1 (13) Å3 | Needle, colorless |
Z = 8 | 0.40 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 2421 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 25.2°, θmin = 1.2° |
ω/2θ scans | h = −40→38 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→8 |
Tmin = 0.914, Tmax = 0.978 | l = 0→19 |
3325 measured reflections | 3 standard reflections every 200 reflections |
3265 independent reflections | intensity decay: none |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.08P)2 + 5P] where P = (Fo2 + 2Fc2)/3 |
3265 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C16H18N4O7S | V = 3622.1 (13) Å3 |
Mr = 410.41 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.831 (7) Å | µ = 0.23 mm−1 |
b = 6.9020 (14) Å | T = 298 K |
c = 16.021 (3) Å | 0.40 × 0.20 × 0.10 mm |
β = 104.48 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2421 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.035 |
Tmin = 0.914, Tmax = 0.978 | 3 standard reflections every 200 reflections |
3325 measured reflections | intensity decay: none |
3265 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.26 e Å−3 |
3265 reflections | Δρmin = −0.31 e Å−3 |
253 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 | ||
S | 0.12664 (2) | 0.14338 (13) | 0.69392 (5) | 0.0401 (2) | |
N1 | 0.07804 (7) | 0.1705 (4) | 0.64572 (16) | 0.0424 (7) | |
H1A | 0.0719 | 0.1836 | 0.5906 | 0.051* | |
O1 | 0.15578 (7) | 0.0798 (4) | 0.92720 (16) | 0.0557 (7) | |
C1 | 0.19376 (12) | −0.2563 (5) | 0.9629 (3) | 0.0570 (10) | |
H1B | 0.2121 | −0.3646 | 0.9704 | 0.085* | |
H1C | 0.1676 | −0.2946 | 0.9278 | 0.085* | |
H1D | 0.1909 | −0.2139 | 1.0182 | 0.085* | |
O2 | 0.20987 (7) | −0.0991 (3) | 0.92109 (16) | 0.0484 (6) | |
N2 | 0.00822 (7) | 0.1970 (4) | 0.63164 (16) | 0.0388 (6) | |
H2A | −0.0114 | 0.1857 | 0.6565 | 0.047* | |
C2 | 0.18727 (9) | 0.0615 (5) | 0.90655 (19) | 0.0379 (7) | |
N3 | 0.02372 (7) | 0.2300 (4) | 0.49733 (16) | 0.0363 (6) | |
O3 | 0.13329 (8) | −0.0390 (4) | 0.73670 (16) | 0.0576 (7) | |
C3 | 0.20669 (9) | 0.2172 (5) | 0.86550 (18) | 0.0356 (7) | |
O4 | 0.14650 (7) | 0.1838 (4) | 0.62677 (15) | 0.0542 (7) | |
N4 | −0.04352 (7) | 0.2765 (4) | 0.51521 (16) | 0.0375 (6) | |
C4 | 0.24906 (9) | 0.2405 (5) | 0.8922 (2) | 0.0432 (8) | |
H4C | 0.2647 | 0.1513 | 0.9300 | 0.052* | |
O5 | 0.05149 (7) | 0.1570 (4) | 0.76305 (14) | 0.0509 (6) | |
C5 | 0.26803 (10) | 0.3949 (5) | 0.8631 (2) | 0.0470 (8) | |
H5A | 0.2962 | 0.4101 | 0.8819 | 0.056* | |
O6 | 0.03580 (7) | 0.2645 (4) | 0.36258 (15) | 0.0531 (6) | |
C6 | 0.24518 (11) | 0.5258 (6) | 0.8063 (2) | 0.0505 (9) | |
H6A | 0.2578 | 0.6302 | 0.7870 | 0.061* | |
O7 | −0.09468 (7) | 0.3699 (4) | 0.39861 (15) | 0.0508 (6) | |
C7 | 0.20337 (10) | 0.5023 (5) | 0.7779 (2) | 0.0468 (8) | |
H7A | 0.1883 | 0.5896 | 0.7382 | 0.056* | |
C8 | 0.18338 (9) | 0.3511 (5) | 0.80731 (19) | 0.0363 (7) | |
C9 | 0.13757 (9) | 0.3323 (5) | 0.7722 (2) | 0.0406 (8) | |
H9A | 0.1264 | 0.4537 | 0.7460 | 0.049* | |
H9B | 0.1249 | 0.3034 | 0.8188 | 0.049* | |
C10 | 0.04638 (9) | 0.1743 (5) | 0.6850 (2) | 0.0369 (7) | |
C11 | −0.00401 (9) | 0.2356 (4) | 0.54321 (19) | 0.0341 (7) | |
C12 | 0.00998 (10) | 0.2704 (5) | 0.4133 (2) | 0.0388 (7) | |
C13 | −0.03018 (10) | 0.3179 (5) | 0.3764 (2) | 0.0438 (8) | |
H13A | −0.0395 | 0.3469 | 0.3181 | 0.053* | |
C14 | −0.05548 (9) | 0.3198 (5) | 0.4314 (2) | 0.0391 (7) | |
C15 | −0.12294 (10) | 0.3408 (6) | 0.4504 (2) | 0.0573 (10) | |
H15A | −0.1496 | 0.3834 | 0.4193 | 0.086* | |
H15B | −0.1143 | 0.4138 | 0.5028 | 0.086* | |
H15C | −0.1239 | 0.2056 | 0.4639 | 0.086* | |
C16 | 0.07680 (10) | 0.1963 (6) | 0.3980 (2) | 0.0597 (10) | |
H16A | 0.0918 | 0.2013 | 0.3545 | 0.090* | |
H16B | 0.0760 | 0.0652 | 0.4175 | 0.090* | |
H16C | 0.0899 | 0.2770 | 0.4457 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0287 (4) | 0.0485 (5) | 0.0398 (4) | 0.0025 (3) | 0.0022 (3) | −0.0034 (4) |
N1 | 0.0293 (13) | 0.0636 (19) | 0.0332 (14) | −0.0023 (13) | 0.0057 (11) | 0.0033 (13) |
O1 | 0.0422 (14) | 0.0684 (17) | 0.0634 (15) | 0.0099 (12) | 0.0260 (12) | 0.0167 (13) |
C1 | 0.067 (2) | 0.041 (2) | 0.065 (2) | −0.0069 (18) | 0.0199 (19) | 0.0080 (19) |
O2 | 0.0434 (13) | 0.0434 (14) | 0.0610 (15) | 0.0055 (10) | 0.0178 (11) | 0.0100 (11) |
N2 | 0.0292 (13) | 0.0450 (16) | 0.0394 (14) | 0.0004 (11) | 0.0035 (11) | 0.0083 (12) |
C2 | 0.0350 (17) | 0.0447 (18) | 0.0313 (15) | 0.0025 (14) | 0.0032 (13) | −0.0006 (14) |
N3 | 0.0344 (14) | 0.0381 (15) | 0.0353 (14) | −0.0032 (11) | 0.0069 (11) | −0.0003 (11) |
O3 | 0.0556 (16) | 0.0440 (15) | 0.0620 (16) | 0.0068 (12) | −0.0061 (12) | 0.0009 (12) |
C3 | 0.0359 (16) | 0.0420 (18) | 0.0281 (14) | −0.0003 (14) | 0.0067 (12) | −0.0035 (13) |
O4 | 0.0377 (13) | 0.0835 (19) | 0.0434 (13) | −0.0003 (12) | 0.0140 (10) | −0.0076 (12) |
N4 | 0.0319 (13) | 0.0339 (14) | 0.0419 (15) | −0.0018 (11) | 0.0001 (11) | 0.0019 (12) |
C4 | 0.0339 (16) | 0.055 (2) | 0.0373 (17) | 0.0008 (15) | 0.0018 (13) | −0.0002 (16) |
O5 | 0.0351 (12) | 0.0769 (18) | 0.0383 (13) | 0.0013 (12) | 0.0046 (10) | 0.0061 (12) |
C5 | 0.0336 (17) | 0.062 (2) | 0.0423 (18) | −0.0094 (16) | 0.0041 (14) | −0.0014 (17) |
O6 | 0.0460 (14) | 0.0707 (17) | 0.0428 (13) | 0.0023 (12) | 0.0117 (11) | 0.0010 (12) |
C6 | 0.049 (2) | 0.057 (2) | 0.0463 (19) | −0.0161 (17) | 0.0120 (16) | 0.0005 (17) |
O7 | 0.0359 (12) | 0.0585 (15) | 0.0513 (14) | 0.0048 (11) | −0.0016 (10) | 0.0134 (12) |
C7 | 0.0469 (19) | 0.050 (2) | 0.0393 (17) | 0.0003 (16) | 0.0035 (15) | 0.0036 (16) |
C8 | 0.0306 (15) | 0.0397 (17) | 0.0360 (16) | −0.0009 (13) | 0.0035 (12) | −0.0060 (14) |
C9 | 0.0344 (16) | 0.0445 (19) | 0.0406 (17) | 0.0049 (14) | 0.0050 (13) | −0.0014 (15) |
C10 | 0.0304 (15) | 0.0371 (17) | 0.0412 (18) | −0.0007 (13) | 0.0052 (13) | 0.0015 (14) |
C11 | 0.0312 (15) | 0.0291 (16) | 0.0389 (16) | −0.0024 (12) | 0.0028 (13) | 0.0013 (13) |
C12 | 0.0439 (18) | 0.0330 (17) | 0.0385 (17) | −0.0033 (14) | 0.0083 (14) | −0.0030 (14) |
C13 | 0.0460 (19) | 0.045 (2) | 0.0340 (16) | −0.0047 (15) | −0.0020 (14) | 0.0006 (14) |
C14 | 0.0363 (17) | 0.0323 (17) | 0.0433 (18) | −0.0011 (13) | −0.0001 (14) | 0.0054 (14) |
C15 | 0.0384 (19) | 0.068 (3) | 0.062 (2) | 0.0021 (18) | 0.0057 (17) | 0.011 (2) |
C16 | 0.0396 (19) | 0.081 (3) | 0.057 (2) | −0.0040 (19) | 0.0105 (16) | −0.009 (2) |
S—O3 | 1.424 (3) | O5—C10 | 1.224 (4) |
S—O4 | 1.431 (2) | C5—C6 | 1.374 (5) |
S—N1 | 1.643 (3) | C5—H5A | 0.930 |
S—C9 | 1.782 (3) | O6—C12 | 1.334 (4) |
N1—C10 | 1.372 (4) | O6—C16 | 1.440 (4) |
N1—H1A | 0.860 | C6—C7 | 1.383 (5) |
O1—C2 | 1.199 (4) | C6—H6A | 0.930 |
C1—O2 | 1.451 (4) | O7—C14 | 1.344 (4) |
C1—H1B | 0.960 | O7—C15 | 1.428 (4) |
C1—H1C | 0.960 | C7—C8 | 1.388 (5) |
C1—H1D | 0.960 | C7—H7A | 0.930 |
O2—C2 | 1.333 (4) | C8—C9 | 1.516 (4) |
N2—C10 | 1.368 (4) | C9—H9A | 0.970 |
N2—C11 | 1.399 (4) | C9—H9B | 0.970 |
N2—H2A | 0.860 | C12—C13 | 1.379 (4) |
C2—C3 | 1.495 (5) | C13—C14 | 1.373 (5) |
N3—C11 | 1.329 (4) | C13—H13A | 0.930 |
N3—C12 | 1.339 (4) | C15—H15A | 0.960 |
C3—C4 | 1.399 (4) | C15—H15B | 0.960 |
C3—C8 | 1.406 (4) | C15—H15C | 0.960 |
N4—C11 | 1.330 (4) | C16—H16A | 0.960 |
N4—C14 | 1.336 (4) | C16—H16B | 0.960 |
C4—C5 | 1.384 (5) | C16—H16C | 0.960 |
C4—H4C | 0.930 | ||
O3—S—O4 | 119.13 (17) | C6—C7—H7A | 119.3 |
O3—S—N1 | 110.25 (15) | C8—C7—H7A | 119.3 |
O4—S—N1 | 103.13 (14) | C7—C8—C3 | 118.6 (3) |
O3—S—C9 | 109.17 (16) | C7—C8—C9 | 118.5 (3) |
O4—S—C9 | 109.40 (16) | C3—C8—C9 | 122.8 (3) |
N1—S—C9 | 104.73 (15) | C8—C9—S | 109.7 (2) |
C10—N1—S | 126.2 (2) | C8—C9—H9A | 109.7 |
C10—N1—H1A | 116.9 | S—C9—H9A | 109.7 |
S—N1—H1A | 116.9 | C8—C9—H9B | 109.7 |
O2—C1—H1B | 109.5 | S—C9—H9B | 109.7 |
O2—C1—H1C | 109.5 | H9A—C9—H9B | 108.2 |
H1B—C1—H1C | 109.5 | O5—C10—N2 | 121.3 (3) |
O2—C1—H1D | 109.5 | O5—C10—N1 | 122.7 (3) |
H1B—C1—H1D | 109.5 | N2—C10—N1 | 116.0 (3) |
H1C—C1—H1D | 109.5 | N3—C11—N4 | 127.5 (3) |
C2—O2—C1 | 115.9 (3) | N3—C11—N2 | 118.9 (3) |
C10—N2—C11 | 130.5 (3) | N4—C11—N2 | 113.6 (3) |
C10—N2—H2A | 114.8 | O6—C12—N3 | 119.4 (3) |
C11—N2—H2A | 114.8 | O6—C12—C13 | 118.1 (3) |
O1—C2—O2 | 123.4 (3) | N3—C12—C13 | 122.5 (3) |
O1—C2—C3 | 124.3 (3) | C14—C13—C12 | 115.6 (3) |
O2—C2—C3 | 112.2 (3) | C14—C13—H13A | 122.2 |
C11—N3—C12 | 115.7 (3) | C12—C13—H13A | 122.2 |
C4—C3—C8 | 119.3 (3) | N4—C14—O7 | 118.1 (3) |
C4—C3—C2 | 118.5 (3) | N4—C14—C13 | 124.2 (3) |
C8—C3—C2 | 121.9 (3) | O7—C14—C13 | 117.7 (3) |
C11—N4—C14 | 114.4 (3) | O7—C15—H15A | 109.5 |
C5—C4—C3 | 120.8 (3) | O7—C15—H15B | 109.5 |
C5—C4—H4C | 119.6 | H15A—C15—H15B | 109.5 |
C3—C4—H4C | 119.6 | O7—C15—H15C | 109.5 |
C6—C5—C4 | 119.8 (3) | H15A—C15—H15C | 109.5 |
C6—C5—H5A | 120.1 | H15B—C15—H15C | 109.5 |
C4—C5—H5A | 120.1 | O6—C16—H16A | 109.5 |
C12—O6—C16 | 118.8 (3) | O6—C16—H16B | 109.5 |
C5—C6—C7 | 120.1 (3) | H16A—C16—H16B | 109.5 |
C5—C6—H6A | 120.0 | O6—C16—H16C | 109.5 |
C7—C6—H6A | 120.0 | H16A—C16—H16C | 109.5 |
C14—O7—C15 | 118.4 (3) | H16B—C16—H16C | 109.5 |
C6—C7—C8 | 121.4 (3) | ||
O3—S—N1—C10 | 61.5 (3) | N1—S—C9—C8 | −167.4 (2) |
O4—S—N1—C10 | −170.2 (3) | C11—N2—C10—O5 | 173.7 (3) |
C9—S—N1—C10 | −55.8 (3) | C11—N2—C10—N1 | −6.9 (5) |
C1—O2—C2—O1 | 1.1 (5) | S—N1—C10—O5 | −0.1 (5) |
C1—O2—C2—C3 | 178.5 (3) | S—N1—C10—N2 | −179.5 (2) |
O1—C2—C3—C4 | 139.0 (3) | C12—N3—C11—N4 | 0.0 (5) |
O2—C2—C3—C4 | −38.4 (4) | C12—N3—C11—N2 | −179.3 (3) |
O1—C2—C3—C8 | −34.9 (5) | C14—N4—C11—N3 | −1.4 (5) |
O2—C2—C3—C8 | 147.7 (3) | C14—N4—C11—N2 | 178.0 (3) |
C8—C3—C4—C5 | 1.0 (5) | C10—N2—C11—N3 | 8.8 (5) |
C2—C3—C4—C5 | −173.1 (3) | C10—N2—C11—N4 | −170.6 (3) |
C3—C4—C5—C6 | −0.9 (5) | C16—O6—C12—N3 | 6.0 (5) |
C4—C5—C6—C7 | −0.5 (5) | C16—O6—C12—C13 | −173.8 (3) |
C5—C6—C7—C8 | 1.9 (5) | C11—N3—C12—O6 | −178.8 (3) |
C6—C7—C8—C3 | −1.7 (5) | C11—N3—C12—C13 | 1.0 (5) |
C6—C7—C8—C9 | −179.0 (3) | O6—C12—C13—C14 | 179.3 (3) |
C4—C3—C8—C7 | 0.3 (4) | N3—C12—C13—C14 | −0.5 (5) |
C2—C3—C8—C7 | 174.2 (3) | C11—N4—C14—O7 | −177.5 (3) |
C4—C3—C8—C9 | 177.5 (3) | C11—N4—C14—C13 | 1.9 (5) |
C2—C3—C8—C9 | −8.7 (5) | C15—O7—C14—N4 | −11.2 (4) |
C7—C8—C9—S | 102.8 (3) | C15—O7—C14—C13 | 169.4 (3) |
C3—C8—C9—S | −74.3 (3) | C12—C13—C14—N4 | −1.0 (5) |
O3—S—C9—C8 | 74.5 (3) | C12—C13—C14—O7 | 178.4 (3) |
O4—S—C9—C8 | −57.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3 | 0.86 | 1.94 | 2.648 (4) | 138 |
N2—H2A···O5i | 0.86 | 2.10 | 2.951 (3) | 170 |
C9—H9B···O1 | 0.97 | 2.36 | 2.970 (4) | 120 |
C15—H15C···O1i | 0.96 | 2.43 | 3.068 (4) | 124 |
Symmetry code: (i) −x, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C16H18N4O7S |
Mr | 410.41 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 33.831 (7), 6.9020 (14), 16.021 (3) |
β (°) | 104.48 (3) |
V (Å3) | 3622.1 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.914, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3325, 3265, 2421 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.156, 1.03 |
No. of reflections | 3265 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.31 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3 | 0.86 | 1.94 | 2.648 (4) | 138 |
N2—H2A···O5i | 0.86 | 2.10 | 2.951 (3) | 170 |
C9—H9B···O1 | 0.97 | 2.36 | 2.970 (4) | 120 |
C15—H15C···O1i | 0.96 | 2.43 | 3.068 (4) | 124 |
Symmetry code: (i) −x, y, −z+3/2. |
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The title compound, bensulfuron-methyl, belongs to the class of systemic sulfonylurea herbicides inhibiting acetolactate synthase, a key enzyme in the biosynthesis of the branched-chain amino acids of target plants (Lee et al., 2002). It is widely used in transplanted and direct-seeded rice fields to control most annual and perennial broadleaved weeds selectively (Sabadie, 1996).
We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the C3–C8 and C11/N3/C12/C13/C14/N4 rings is 50.00 (15)°. There are intramolecular N1—H1A···N3 and C9—H9B···O1 hydrogen bonds (Fig. 1), and intermolecular N—H···O and C—H···O hydrogen bonds form centrosymmetric dimers (Fig. 2).