organic compounds
of cyclosulfamuron
aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr
The title compound (systematic name: 1-{[2-(cyclopropylcarbonyl)anilino]sulfonyl}-3-(4,6-dimethoxypyrimidin-2-yl)urea), C17H19N5O6S, is a pyrimidinylsulfonylurea herbicide. The dihedral angles between the mean planes of the central benzene ring and the cyclopropyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. The C atoms of the methoxy groups lie almost in the plane of the pyrimidine ring [deviations = 0.043 (2) and 0.028 (2) Å] and intramolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds all close S(6) rings. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds and weak π–π interactions [centroid–centroid distances = 3.6175 (9) and 3.7068 (9) Å] link adjacent molecules, forming a three-dimensional network.
Keywords: crystal structure; hydrogen bonding; π–π interactions.
CCDC reference: 1415211
1. Related literature
For information on the herbicidal properties of the title compound, see: Sarıgül & İnam (2009). For a related see: Xia et al. (2008).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 1415211
https://doi.org/10.1107/S2056989015014115/hb7470sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014115/hb7470Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014115/hb7470Isup3.cml
The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.
All H-atoms were positioned geometrically and refined using a riding model with d(N—H) = 0.88 Å, Uiso = 1.2Ueq(C) for N—H group, d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H. d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.
Cyclosulfamuron [systematic name: 1-[2-(cyclopropylcarbonyl)anilinosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea] is a pyrimidinylsulfonylurea herbicide and has been widely used to control weeds because of their low toxicity to mammals and their high herbicidal activity (Sarıgül & Inam, 2009). However, until now its
has not been reported. In the title compound (Fig. 1), the dihedral angles between the mean planes of the central phenyl ring and the cyclopropyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in a similar (Xia et al., 2008).In the π–π interactions.
(Fig. 2), N—H···O and C—H···O hydrogen bonds are observed (Table 1). In addition, weak intermolecular Cg1···Cg1v and Cg1···Cg2vi (Cg1 and Cg2 are the centroids of the N4—C12—N5—C15—C14—C13 and C5–C10 rings, respectively) interactions are present [for symmetry codes: (v), -x + 2, -y, -z + 1, (vi), x + 1/2, -y + 1/2, z + 1/2]. A three-dimensional network is formed by the hydrogen bonds andFor information on the herbicidal properties of the title compound, see: Sarıgül & Inam (2009). For a related
see: Xia et al. (2008).Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. | |
Fig. 2. Crystal packing viewed along the c axis. The intermolecular interactions are shown as dashed lines. |
C17H19N5O6S | F(000) = 880 |
Mr = 421.43 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.7019 (4) Å | Cell parameters from 6977 reflections |
b = 9.6216 (3) Å | θ = 2.6–27.4° |
c = 15.6213 (5) Å | µ = 0.22 mm−1 |
β = 93.6194 (12)° | T = 173 K |
V = 1905.31 (10) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.27 × 0.23 mm |
Bruker APEXII CCD diffractometer | 3688 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.030 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | θmax = 27.5°, θmin = 2.0° |
Tmin = 0.934, Tmax = 0.952 | h = −16→15 |
17544 measured reflections | k = −12→12 |
4365 independent reflections | l = −20→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0579P)2 + 0.7248P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4365 reflections | Δρmax = 0.22 e Å−3 |
264 parameters | Δρmin = −0.49 e Å−3 |
C17H19N5O6S | V = 1905.31 (10) Å3 |
Mr = 421.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.7019 (4) Å | µ = 0.22 mm−1 |
b = 9.6216 (3) Å | T = 173 K |
c = 15.6213 (5) Å | 0.32 × 0.27 × 0.23 mm |
β = 93.6194 (12)° |
Bruker APEXII CCD diffractometer | 4365 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3688 reflections with I > 2σ(I) |
Tmin = 0.934, Tmax = 0.952 | Rint = 0.030 |
17544 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.22 e Å−3 |
4365 reflections | Δρmin = −0.49 e Å−3 |
264 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 1.03274 (3) | 0.41778 (4) | 0.19915 (2) | 0.02564 (12) | |
O1 | 1.02757 (11) | 0.25129 (16) | −0.03440 (8) | 0.0524 (4) | |
O2 | 1.12410 (9) | 0.48608 (12) | 0.17159 (7) | 0.0340 (3) | |
O3 | 0.95254 (9) | 0.49585 (12) | 0.23699 (7) | 0.0343 (3) | |
O4 | 1.19071 (9) | 0.18921 (12) | 0.19997 (7) | 0.0335 (3) | |
O5 | 0.94327 (9) | 0.31556 (13) | 0.52112 (7) | 0.0386 (3) | |
O6 | 1.17908 (10) | −0.04334 (14) | 0.61128 (7) | 0.0429 (3) | |
N1 | 0.98567 (10) | 0.33405 (14) | 0.11638 (8) | 0.0290 (3) | |
H1N | 1.0187 | 0.3456 | 0.0690 | 0.035* | |
N2 | 1.06665 (10) | 0.30293 (14) | 0.27345 (8) | 0.0281 (3) | |
H2N | 1.0317 | 0.3014 | 0.3203 | 0.034* | |
N3 | 1.17533 (10) | 0.13526 (15) | 0.33969 (8) | 0.0303 (3) | |
H3N | 1.2279 | 0.0767 | 0.3351 | 0.036* | |
N4 | 1.05707 (10) | 0.22678 (14) | 0.43352 (8) | 0.0284 (3) | |
N5 | 1.17993 (10) | 0.04736 (14) | 0.47520 (8) | 0.0302 (3) | |
C1 | 1.00581 (16) | 0.0853 (2) | −0.18258 (11) | 0.0418 (4) | |
H1A | 1.0695 | 0.1442 | −0.1740 | 0.050* | |
H1B | 1.0162 | −0.0019 | −0.2147 | 0.050* | |
C2 | 0.90252 (18) | 0.1560 (2) | −0.19567 (11) | 0.0492 (5) | |
H2A | 0.8486 | 0.1127 | −0.2357 | 0.059* | |
H2B | 0.9019 | 0.2589 | −0.1950 | 0.059* | |
C3 | 0.93094 (14) | 0.08205 (17) | −0.11251 (10) | 0.0354 (4) | |
H3 | 0.8943 | −0.0082 | −0.1031 | 0.042* | |
C4 | 0.95231 (14) | 0.17112 (17) | −0.03618 (10) | 0.0334 (4) | |
C5 | 0.88087 (12) | 0.16383 (17) | 0.03524 (10) | 0.0301 (3) | |
C6 | 0.79319 (14) | 0.0755 (2) | 0.02989 (12) | 0.0415 (4) | |
H6 | 0.7797 | 0.0215 | −0.0206 | 0.050* | |
C7 | 0.72575 (15) | 0.0639 (2) | 0.09523 (13) | 0.0462 (5) | |
H7 | 0.6672 | 0.0023 | 0.0901 | 0.055* | |
C8 | 0.74454 (14) | 0.1432 (2) | 0.16818 (12) | 0.0432 (4) | |
H8 | 0.6987 | 0.1354 | 0.2137 | 0.052* | |
C9 | 0.82919 (13) | 0.23370 (19) | 0.17609 (10) | 0.0347 (4) | |
H9 | 0.8403 | 0.2886 | 0.2264 | 0.042* | |
C10 | 0.89805 (12) | 0.24451 (16) | 0.11062 (9) | 0.0267 (3) | |
C11 | 1.14737 (12) | 0.20858 (16) | 0.26595 (9) | 0.0267 (3) | |
C12 | 1.13446 (12) | 0.13831 (16) | 0.42007 (9) | 0.0272 (3) | |
C13 | 1.01967 (12) | 0.22237 (17) | 0.51212 (9) | 0.0294 (3) | |
C14 | 1.05796 (13) | 0.13144 (18) | 0.57482 (9) | 0.0325 (4) | |
H14 | 1.0303 | 0.1274 | 0.6299 | 0.039* | |
C15 | 1.13996 (13) | 0.04587 (18) | 0.55188 (10) | 0.0314 (3) | |
C16 | 0.89737 (16) | 0.3201 (2) | 0.60284 (11) | 0.0514 (5) | |
H16A | 0.8605 | 0.2326 | 0.6124 | 0.077* | |
H16B | 0.8472 | 0.3974 | 0.6035 | 0.077* | |
H16C | 0.9531 | 0.3336 | 0.6484 | 0.077* | |
C17 | 1.26553 (16) | −0.1300 (2) | 0.58797 (12) | 0.0463 (5) | |
H17A | 1.2435 | −0.1851 | 0.5372 | 0.069* | |
H17B | 1.2862 | −0.1925 | 0.6357 | 0.069* | |
H17C | 1.3256 | −0.0714 | 0.5752 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0234 (2) | 0.0291 (2) | 0.02454 (19) | −0.00228 (14) | 0.00254 (14) | −0.00382 (13) |
O1 | 0.0535 (9) | 0.0729 (10) | 0.0323 (6) | −0.0295 (7) | 0.0133 (6) | −0.0169 (6) |
O2 | 0.0313 (6) | 0.0348 (6) | 0.0362 (6) | −0.0109 (5) | 0.0052 (5) | −0.0047 (5) |
O3 | 0.0321 (6) | 0.0368 (6) | 0.0343 (6) | 0.0076 (5) | 0.0039 (5) | −0.0045 (5) |
O4 | 0.0305 (6) | 0.0445 (7) | 0.0263 (5) | 0.0045 (5) | 0.0096 (4) | −0.0049 (5) |
O5 | 0.0368 (7) | 0.0544 (8) | 0.0255 (6) | 0.0162 (6) | 0.0090 (5) | −0.0010 (5) |
O6 | 0.0459 (8) | 0.0518 (8) | 0.0309 (6) | 0.0133 (6) | 0.0007 (5) | 0.0070 (5) |
N1 | 0.0263 (7) | 0.0387 (7) | 0.0222 (6) | −0.0083 (6) | 0.0039 (5) | −0.0029 (5) |
N2 | 0.0243 (7) | 0.0385 (7) | 0.0221 (6) | 0.0048 (5) | 0.0055 (5) | −0.0010 (5) |
N3 | 0.0256 (7) | 0.0394 (7) | 0.0263 (6) | 0.0096 (6) | 0.0059 (5) | −0.0015 (5) |
N4 | 0.0253 (7) | 0.0370 (7) | 0.0232 (6) | 0.0037 (5) | 0.0039 (5) | −0.0023 (5) |
N5 | 0.0263 (7) | 0.0368 (7) | 0.0274 (6) | 0.0026 (6) | 0.0016 (5) | −0.0017 (5) |
C1 | 0.0512 (11) | 0.0429 (10) | 0.0312 (8) | 0.0058 (8) | 0.0010 (8) | −0.0081 (7) |
C2 | 0.0760 (15) | 0.0388 (10) | 0.0310 (9) | 0.0193 (10) | −0.0112 (9) | −0.0048 (7) |
C3 | 0.0467 (10) | 0.0305 (8) | 0.0283 (8) | 0.0018 (7) | −0.0033 (7) | −0.0030 (6) |
C4 | 0.0368 (9) | 0.0366 (9) | 0.0262 (7) | −0.0024 (7) | −0.0031 (6) | −0.0015 (6) |
C5 | 0.0270 (8) | 0.0333 (8) | 0.0292 (7) | −0.0029 (6) | −0.0049 (6) | 0.0009 (6) |
C6 | 0.0348 (10) | 0.0436 (10) | 0.0451 (10) | −0.0099 (8) | −0.0048 (8) | −0.0083 (8) |
C7 | 0.0301 (9) | 0.0511 (11) | 0.0571 (11) | −0.0163 (8) | −0.0002 (8) | −0.0050 (9) |
C8 | 0.0282 (9) | 0.0552 (11) | 0.0471 (10) | −0.0093 (8) | 0.0086 (7) | 0.0018 (9) |
C9 | 0.0255 (8) | 0.0450 (10) | 0.0338 (8) | −0.0062 (7) | 0.0027 (6) | −0.0025 (7) |
C10 | 0.0220 (7) | 0.0304 (8) | 0.0272 (7) | −0.0022 (6) | −0.0019 (6) | 0.0015 (6) |
C11 | 0.0209 (7) | 0.0342 (8) | 0.0252 (7) | −0.0015 (6) | 0.0030 (5) | −0.0046 (6) |
C12 | 0.0234 (7) | 0.0346 (8) | 0.0238 (7) | −0.0015 (6) | 0.0017 (6) | −0.0037 (6) |
C13 | 0.0260 (8) | 0.0379 (8) | 0.0244 (7) | 0.0015 (6) | 0.0033 (6) | −0.0057 (6) |
C14 | 0.0328 (9) | 0.0429 (9) | 0.0220 (7) | 0.0020 (7) | 0.0036 (6) | −0.0029 (6) |
C15 | 0.0287 (8) | 0.0383 (9) | 0.0270 (7) | −0.0005 (7) | −0.0013 (6) | −0.0006 (6) |
C16 | 0.0513 (12) | 0.0780 (15) | 0.0262 (8) | 0.0277 (11) | 0.0122 (8) | −0.0043 (9) |
C17 | 0.0476 (11) | 0.0523 (11) | 0.0379 (9) | 0.0167 (9) | −0.0058 (8) | 0.0016 (8) |
S1—O2 | 1.4237 (11) | C2—C3 | 1.505 (2) |
S1—O3 | 1.4238 (11) | C2—H2A | 0.9900 |
S1—N1 | 1.6065 (12) | C2—H2B | 0.9900 |
S1—N2 | 1.6402 (13) | C3—C4 | 1.480 (2) |
O1—C4 | 1.227 (2) | C3—H3 | 1.0000 |
O4—C11 | 1.2132 (17) | C4—C5 | 1.484 (2) |
O5—C13 | 1.3351 (19) | C5—C6 | 1.399 (2) |
O5—C16 | 1.4372 (19) | C5—C10 | 1.416 (2) |
O6—C15 | 1.3366 (19) | C6—C7 | 1.378 (3) |
O6—C17 | 1.444 (2) | C6—H6 | 0.9500 |
N1—C10 | 1.4058 (19) | C7—C8 | 1.379 (3) |
N1—H1N | 0.8800 | C7—H7 | 0.9500 |
N2—C11 | 1.3799 (19) | C8—C9 | 1.383 (2) |
N2—H2N | 0.8800 | C8—H8 | 0.9500 |
N3—C11 | 1.378 (2) | C9—C10 | 1.391 (2) |
N3—C12 | 1.3890 (18) | C9—H9 | 0.9500 |
N3—H3N | 0.8800 | C13—C14 | 1.379 (2) |
N4—C12 | 1.327 (2) | C14—C15 | 1.392 (2) |
N4—C13 | 1.3449 (19) | C14—H14 | 0.9500 |
N5—C15 | 1.3303 (19) | C16—H16A | 0.9800 |
N5—C12 | 1.333 (2) | C16—H16B | 0.9800 |
C1—C2 | 1.480 (3) | C16—H16C | 0.9800 |
C1—C3 | 1.495 (2) | C17—H17A | 0.9800 |
C1—H1A | 0.9900 | C17—H17B | 0.9800 |
C1—H1B | 0.9900 | C17—H17C | 0.9800 |
O2—S1—O3 | 120.02 (7) | C7—C6—C5 | 122.31 (17) |
O2—S1—N1 | 104.90 (7) | C7—C6—H6 | 118.8 |
O3—S1—N1 | 111.04 (7) | C5—C6—H6 | 118.8 |
O2—S1—N2 | 110.02 (7) | C6—C7—C8 | 118.96 (17) |
O3—S1—N2 | 102.97 (7) | C6—C7—H7 | 120.5 |
N1—S1—N2 | 107.42 (7) | C8—C7—H7 | 120.5 |
C13—O5—C16 | 116.90 (13) | C7—C8—C9 | 120.99 (17) |
C15—O6—C17 | 116.82 (13) | C7—C8—H8 | 119.5 |
C10—N1—S1 | 127.72 (10) | C9—C8—H8 | 119.5 |
C10—N1—H1N | 116.1 | C8—C9—C10 | 120.18 (16) |
S1—N1—H1N | 116.1 | C8—C9—H9 | 119.9 |
C11—N2—S1 | 123.13 (10) | C10—C9—H9 | 119.9 |
C11—N2—H2N | 118.4 | C9—C10—N1 | 122.06 (14) |
S1—N2—H2N | 118.4 | C9—C10—C5 | 119.97 (14) |
C11—N3—C12 | 130.81 (13) | N1—C10—C5 | 117.98 (13) |
C11—N3—H3N | 114.6 | O4—C11—N3 | 121.65 (14) |
C12—N3—H3N | 114.6 | O4—C11—N2 | 123.54 (14) |
C12—N4—C13 | 115.60 (13) | N3—C11—N2 | 114.81 (12) |
C15—N5—C12 | 114.47 (13) | N4—C12—N5 | 127.86 (14) |
C2—C1—C3 | 60.76 (12) | N4—C12—N3 | 118.65 (14) |
C2—C1—H1A | 117.7 | N5—C12—N3 | 113.49 (13) |
C3—C1—H1A | 117.7 | O5—C13—N4 | 112.08 (13) |
C2—C1—H1B | 117.7 | O5—C13—C14 | 125.27 (14) |
C3—C1—H1B | 117.7 | N4—C13—C14 | 122.65 (14) |
H1A—C1—H1B | 114.8 | C13—C14—C15 | 115.36 (14) |
C1—C2—C3 | 60.10 (12) | C13—C14—H14 | 122.3 |
C1—C2—H2A | 117.8 | C15—C14—H14 | 122.3 |
C3—C2—H2A | 117.8 | N5—C15—O6 | 119.06 (15) |
C1—C2—H2B | 117.8 | N5—C15—C14 | 124.04 (15) |
C3—C2—H2B | 117.8 | O6—C15—C14 | 116.89 (14) |
H2A—C2—H2B | 114.9 | O5—C16—H16A | 109.5 |
C4—C3—C1 | 119.02 (16) | O5—C16—H16B | 109.5 |
C4—C3—C2 | 116.34 (14) | H16A—C16—H16B | 109.5 |
C1—C3—C2 | 59.14 (12) | O5—C16—H16C | 109.5 |
C4—C3—H3 | 116.6 | H16A—C16—H16C | 109.5 |
C1—C3—H3 | 116.6 | H16B—C16—H16C | 109.5 |
C2—C3—H3 | 116.6 | O6—C17—H17A | 109.5 |
O1—C4—C3 | 119.04 (15) | O6—C17—H17B | 109.5 |
O1—C4—C5 | 121.68 (14) | H17A—C17—H17B | 109.5 |
C3—C4—C5 | 119.26 (15) | O6—C17—H17C | 109.5 |
C6—C5—C10 | 117.59 (15) | H17A—C17—H17C | 109.5 |
C6—C5—C4 | 120.40 (15) | H17B—C17—H17C | 109.5 |
C10—C5—C4 | 122.01 (14) | ||
O2—S1—N1—C10 | 176.89 (13) | C4—C5—C10—C9 | −179.69 (15) |
O3—S1—N1—C10 | −52.05 (15) | C6—C5—C10—N1 | −179.72 (15) |
N2—S1—N1—C10 | 59.84 (15) | C4—C5—C10—N1 | 0.3 (2) |
O2—S1—N2—C11 | −47.34 (14) | C12—N3—C11—O4 | −177.90 (15) |
O3—S1—N2—C11 | −176.41 (12) | C12—N3—C11—N2 | 1.5 (2) |
N1—S1—N2—C11 | 66.31 (13) | S1—N2—C11—O4 | −10.3 (2) |
C2—C1—C3—C4 | −105.05 (18) | S1—N2—C11—N3 | 170.31 (11) |
C1—C2—C3—C4 | 109.56 (18) | C13—N4—C12—N5 | −0.8 (2) |
C1—C3—C4—O1 | 4.1 (2) | C13—N4—C12—N3 | 178.68 (14) |
C2—C3—C4—O1 | −63.6 (2) | C15—N5—C12—N4 | 1.3 (2) |
C1—C3—C4—C5 | −177.36 (15) | C15—N5—C12—N3 | −178.23 (14) |
C2—C3—C4—C5 | 114.96 (19) | C11—N3—C12—N4 | −2.0 (2) |
O1—C4—C5—C6 | 177.40 (17) | C11—N3—C12—N5 | 177.54 (15) |
C3—C4—C5—C6 | −1.1 (2) | C16—O5—C13—N4 | −179.99 (16) |
O1—C4—C5—C10 | −2.6 (3) | C16—O5—C13—C14 | −0.3 (2) |
C3—C4—C5—C10 | 178.88 (14) | C12—N4—C13—O5 | 179.06 (13) |
C10—C5—C6—C7 | −1.0 (3) | C12—N4—C13—C14 | −0.6 (2) |
C4—C5—C6—C7 | 179.00 (18) | O5—C13—C14—C15 | −178.31 (15) |
C5—C6—C7—C8 | 0.7 (3) | N4—C13—C14—C15 | 1.3 (2) |
C6—C7—C8—C9 | 0.4 (3) | C12—N5—C15—O6 | 178.96 (14) |
C7—C8—C9—C10 | −1.0 (3) | C12—N5—C15—C14 | −0.4 (2) |
C8—C9—C10—N1 | −179.31 (16) | C17—O6—C15—N5 | 1.8 (2) |
C8—C9—C10—C5 | 0.7 (3) | C17—O6—C15—C14 | −178.78 (15) |
S1—N1—C10—C9 | 10.3 (2) | C13—C14—C15—N5 | −0.8 (2) |
S1—N1—C10—C5 | −169.74 (12) | C13—C14—C15—O6 | 179.85 (15) |
C6—C5—C10—C9 | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 1.86 | 2.5736 (18) | 137 |
N2—H2N···N4 | 0.88 | 1.92 | 2.6158 (18) | 135 |
C9—H9···O3 | 0.95 | 2.45 | 3.088 (2) | 124 |
N3—H3N···O2i | 0.88 | 2.08 | 2.9391 (17) | 165 |
C2—H2B···O2ii | 0.99 | 2.51 | 3.483 (2) | 169 |
C3—H3···O4iii | 1.00 | 2.51 | 3.286 (2) | 135 |
C8—H8···O3iv | 0.95 | 2.50 | 3.307 (2) | 142 |
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 1.86 | 2.5736 (18) | 137 |
N2—H2N···N4 | 0.88 | 1.92 | 2.6158 (18) | 135 |
C9—H9···O3 | 0.95 | 2.45 | 3.088 (2) | 124 |
N3—H3N···O2i | 0.88 | 2.08 | 2.9391 (17) | 165 |
C2—H2B···O2ii | 0.99 | 2.51 | 3.483 (2) | 169 |
C3—H3···O4iii | 1.00 | 2.51 | 3.286 (2) | 135 |
C8—H8···O3iv | 0.95 | 2.50 | 3.307 (2) | 142 |
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+3/2, y−1/2, −z+1/2. |
Acknowledgements
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).
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Cyclosulfamuron [systematic name: 1-[2-(cyclopropylcarbonyl)anilinosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea] is a pyrimidinylsulfonylurea herbicide and has been widely used to control weeds because of their low toxicity to mammals and their high herbicidal activity (Sarıgül & Inam, 2009). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angles between the mean planes of the central phenyl ring and the cyclopropyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Xia et al., 2008).
In the crystal structure (Fig. 2), N—H···O and C—H···O hydrogen bonds are observed (Table 1). In addition, weak intermolecular Cg1···Cg1v and Cg1···Cg2vi (Cg1 and Cg2 are the centroids of the N4—C12—N5—C15—C14—C13 and C5–C10 rings, respectively) interactions are present [for symmetry codes: (v), -x + 2, -y, -z + 1, (vi), x + 1/2, -y + 1/2, z + 1/2]. A three-dimensional network is formed by the hydrogen bonds and π–π interactions.