Crystal structure of flucetosulfuron

Hyunjin Park; Jineun Kim; Eunjin Kwon; Tae Ho Kim

doi:10.1107/S2056989017012737

. 2017 Sep 12;73(Pt 10):1439–1442. doi: 10.1107/S2056989017012737

Crystal structure of flucetosulfuron

Hyunjin Park ^a, Jineun Kim ^a,^*, Eunjin Kwon ^a, Tae Ho Kim ^a,^*

PMCID: PMC5730291 PMID: 29250354

The title compound, C₁₈H₂₂FN₅O₈S, is used as a herbicide. The crystal structure is stabilized by N/C—H⋯O hydrogen bond, C—H⋯F and C—H⋯π interactions with weak π–π interactions contacts to form a three-dimensional architecture.

Keywords: crystal structure, herbicides, pyrimidinylsulfonylurea herbicide, flucetosulfuron

Abstract

The title compound, {systematic name: 1-[3-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl)pyridin-2-yl]-2-fluoropropyl 2-methoxyacetate}, C₁₈H₂₂FN₅O₈S, is used as a herbicide (pyrimidinylsulfonylurea herbicide). The dihedral angle between the mean planes of the pyridine and pyrimidine rings is 86.90 (7)°. In the crystal, N/C—H⋯O hydrogen bonds, C—H⋯F and C—H⋯π interactions link adjacent molecules, forming a chain along [020]. A further two C—H⋯O hydrogen bonds together with weak π–π interactions [ring centroid separation = 3.7584 (12) Å] further aggregate the structure into a three-dimensional architecture.

Chemical context

Flucetosulfuron, a relatively new herbicide, inhibits acetolactate synthase (ALS) in plants, as do other ALS inhibitors such as imidazolinones, pyrimidinyloxybenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones (Lee et al., 2014 ▸). It is a novel post-emergence sulfonylurea herbicide providing excellent control of Galium aparine and other important broadleaf weeds with good safety to cereal crops, wheat and barley (Kim, Lee et al., 2003 ▸) In rice, the herbicide provides excellent control of Echinochloa crus-galli, which is not or only marginally controlled by common sulfonylurea products, and also controls annual broadleaf weeds, sedges and perennial weeds of rice with similar efficacy to other sulfonylurea rice herbicides (Kim, Koo et al., 2003 ▸). Until now, its crystal structure had not been reported and we describe it herein.

Structural commentary

The structure of flucetosulfuron is shown in Fig. 1 ▸. The dihedral angle between the mean planes of the pyridine and pyrimidine rings is 86.90 (7)°. All bond lengths and angles are normal and comparable to those observed in similar crystal structures (Jeon et al., 2015 ▸; Chopra et al., 2004 ▸).

The molecular structure of the title compound with the atom labelling and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Supramolecular features

In the crystal, molecules are linked by C1—H1A⋯O3ⁱ, N3—H3N⋯O8ⁱ and C2—H2B⋯F1ⁱⁱ hydrogen bonds [H⋯O = 2.58, 2.01 and H⋯F = 2.53 Å; Table 1 ▸] and C1—H1B⋯Cg1ⁱ interactions [H⋯π = 2.74 Å], forming a chain structure along [020] (yellow dashed lines in Fig. 2 ▸). In addition, the chains are linked by C12—H12⋯O2ⁱⁱⁱ hydrogen bonds [H⋯O =2.42 Å], forming a two-dimensional network structure parallel to (020) (red dashed lines in Fig. 2 ▸). The C17—H17⋯O5^iv hydrogen bond [H⋯O =2.55 Å] and weak π–π interactions (N1–N2/C3–C6) [Cg2⋯Cg2^v= 3.7584 (12) Å; symmetry code: (v) −x + 2, −y + 1, −z + 1] generate a three-dimensional architecture with molecules stacked along the a-axis direction (black dashed lines in Fig. 3 ▸).

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the N5/C8–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O8ⁱ	0.88	2.01	2.885 (2)	174
C1—H1A⋯O3ⁱ	0.98	2.58	3.368 (3)	137
C2—H2B⋯F1ⁱⁱ	0.98	2.53	3.161 (2)	122
C12—H12⋯O2ⁱⁱⁱ	0.95	2.42	3.229 (3)	143
C17—H17A⋯O5^iv	0.99	2.55	3.367 (3)	139
C1—H1B⋯Cg1ⁱ	0.98	2.74	3.488 (2)	134

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

The N/C—H⋯O hydrogen bond, C—H⋯F and C—H⋯π interactions (yellow dashed lines) link adjacent molecules, forming chains along [020]. The chains are further linked by C—H⋯O hydrogen bonds (red dashed lines), forming a two-dimensional network parallel to (020). H atoms have been omitted for clarity.

A packing diagram showing the three-dimensional architecture formed by intermolecular C—H⋯O hydrogen bonds (red dashed lines) and π–π interactions (black dashed lines). H atoms have been omitted for clarity.

Database survey

We have reported the crystal structures of several pesticides including compounds with pyrimidinylsulfonylurea, dimethoxypyrimidin and sulfonylurea ring (Kang et al., 2015 ▸; Jeon et al., 2015 ▸; Kwon et al., 2016 ▸). Moreover, a database search (CSD Version 5.27, last update February 2017; Groom et al., 2016 ▸) yielded other comparable structures, methyl 2-{[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonylmethyl}benzoate (Xia et al., 2008 ▸), 2-amino-4,6-dimethoxypyrimidin-1-ium 2,2-dichloroacetate (Lin et al., 2012 ▸), N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide (Wu et al., 2012 ▸) and 4-{4-[N-(5,6-dimethoxypyrimidin-4-yl)sulfamoyl]phenylcarbamoyl}-2,6-dimethoxyphenyl acetate (Pan et al., 2012 ▸).

Synthesis and crystallization

The title compound was purchased from Dr Ehrenstorfer GmbH. Colourless single crystals suitable for X-ray diffraction were obtained from a CH₃CN solution by slow evaporation at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were positioned geometrically and refined using a riding model with d(N—H) = 0.88 Å, U _iso = 1.2U _eq(C) for urea N—H, d(C—H) = 0.95 Å, U _iso = 1.2U _eq(C) for aromatic C—H, d(C—H) = 0.98 Å, U _iso = 1.5U _eq(C) for methyl groups, d(C—H) = 0.99 Å, U _iso = 1.2U _eq(C) for CH₂ group, d(C—H) = 1.00 Å, U _iso = 1.5U _eq(C) for Csp ³—H.

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₈H₂₂FN₅O₈S
M _r	487.46
Crystal system, space group	Triclinic, P
Temperature (K)	173
a, b, c (Å)	8.3993 (3), 9.1030 (3), 15.6862 (5)
α, β, γ (°)	92.116 (2), 101.113 (2), 112.810 (2)
V (Å³)	1076.53 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.22
Crystal size (mm)	0.36 × 0.06 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 ▸)
T _min, T _max	0.702, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10919, 3773, 3081
R _int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.039, 0.099, 1.06
No. of reflections	3773
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

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Computer programs: APEX2 and SAINT (Bruker, 2014 ▸), SHELXS97 and SHELXTL (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), DIAMOND (Brandenburg, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989017012737/hg5495sup1.cif

e-73-01439-sup1.cif^{(384.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017012737/hg5495Isup2.hkl

e-73-01439-Isup2.hkl^{(300.8KB, hkl)}

CCDC reference: 1572854

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Crystal data

C₁₈H₂₂FN₅O₈S	Z = 2
M_r = 487.46	F(000) = 508
Triclinic, P1	D_x = 1.504 Mg m⁻³
a = 8.3993 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1030 (3) Å	Cell parameters from 3325 reflections
c = 15.6862 (5) Å	θ = 2.5–26.9°
α = 92.116 (2)°	µ = 0.22 mm⁻¹
β = 101.113 (2)°	T = 173 K
γ = 112.810 (2)°	Needle, colourless
V = 1076.53 (6) Å³	0.36 × 0.06 × 0.05 mm

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Data collection

Bruker APEXII CCD diffractometer	3081 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.031
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 25.0°, θ_min = 1.3°
T_min = 0.702, T_max = 0.746	h = −9→9
10919 measured reflections	k = −10→10
3773 independent reflections	l = −18→18

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Refinement

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) = 0.099	w = 1/[σ²(F_o²) + (0.0439P)² + 0.337P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3773 reflections	Δρ_max = 0.45 e Å⁻³
302 parameters	Δρ_min = −0.39 e Å⁻³

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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
S1	0.39351 (7)	0.10312 (6)	0.18674 (3)	0.02316 (15)
F1	0.2117 (2)	0.35690 (17)	−0.01327 (8)	0.0529 (4)
O1	1.0327 (2)	0.78934 (17)	0.56837 (9)	0.0345 (4)
O2	0.97933 (18)	0.63951 (17)	0.27393 (9)	0.0268 (3)
O3	0.34138 (19)	0.08587 (18)	0.37121 (9)	0.0309 (4)
O4	0.48165 (18)	0.18107 (17)	0.12133 (9)	0.0278 (4)
O5	0.3822 (2)	−0.05369 (17)	0.20150 (10)	0.0330 (4)
O6	0.26027 (17)	0.48834 (16)	0.21292 (8)	0.0226 (3)
O7	0.55822 (19)	0.62252 (18)	0.24672 (9)	0.0302 (4)
O8	0.53183 (18)	0.72872 (16)	0.41130 (9)	0.0262 (4)
N1	0.8060 (2)	0.5524 (2)	0.49899 (11)	0.0227 (4)
N2	0.7821 (2)	0.4766 (2)	0.34862 (10)	0.0213 (4)
N3	0.5794 (2)	0.3194 (2)	0.42532 (11)	0.0249 (4)
H3N	0.5538	0.3064	0.4771	0.030*
N4	0.4990 (2)	0.2289 (2)	0.27617 (10)	0.0252 (4)
H4N	0.5839	0.3209	0.2718	0.030*
N5	−0.0364 (2)	0.2072 (2)	0.11793 (12)	0.0310 (4)
C1	0.9641 (3)	0.7561 (3)	0.64590 (14)	0.0356 (6)
H1A	0.8389	0.7393	0.6326	0.053*
H1B	1.0313	0.8472	0.6918	0.053*
H1C	0.9752	0.6593	0.6662	0.053*
C2	0.8773 (3)	0.5257 (3)	0.19662 (13)	0.0285 (5)
H2A	0.8717	0.4188	0.2079	0.043*
H2B	0.9342	0.5588	0.1475	0.043*
H2C	0.7571	0.5224	0.1821	0.043*
C3	0.9464 (3)	0.6843 (2)	0.49563 (13)	0.0238 (5)
C4	0.7292 (3)	0.4557 (2)	0.42344 (13)	0.0207 (4)
C5	0.9225 (3)	0.6125 (2)	0.34821 (13)	0.0215 (5)
C6	1.0123 (3)	0.7244 (2)	0.42113 (13)	0.0253 (5)
H6	1.1113	0.8211	0.4205	0.030*
C7	0.4640 (3)	0.2007 (2)	0.35825 (13)	0.0234 (5)
C8	0.1749 (3)	0.0953 (2)	0.16496 (12)	0.0209 (5)
C9	0.1326 (3)	0.2238 (2)	0.13956 (13)	0.0229 (5)
C10	−0.1640 (3)	0.0645 (3)	0.12140 (15)	0.0358 (6)
H10	−0.2836	0.0525	0.1041	0.043*
C11	−0.1331 (3)	−0.0655 (3)	0.14834 (15)	0.0356 (6)
H11	−0.2283	−0.1633	0.1518	0.043*
C12	0.0406 (3)	−0.0500 (3)	0.17037 (14)	0.0303 (5)
H12	0.0674	−0.1376	0.1889	0.036*
C13	0.2671 (3)	0.3930 (2)	0.13829 (12)	0.0219 (5)
H13	0.3884	0.3942	0.1447	0.026*
C14	0.2184 (3)	0.4629 (3)	0.05544 (13)	0.0320 (5)
H14	0.0981	0.4629	0.0509	0.038*
C15	0.3463 (3)	0.6282 (3)	0.04812 (15)	0.0416 (6)
H15A	0.3513	0.7036	0.0959	0.062*
H15B	0.3069	0.6609	−0.0082	0.062*
H15C	0.4642	0.6286	0.0519	0.062*
C16	0.4167 (3)	0.5958 (2)	0.26289 (13)	0.0210 (5)
C17	0.3826 (3)	0.6730 (3)	0.34038 (12)	0.0240 (5)
H17A	0.3527	0.7642	0.3228	0.029*
H17B	0.2799	0.5939	0.3590	0.029*
C18	0.6598 (3)	0.8857 (3)	0.40752 (15)	0.0316 (5)
H18A	0.7041	0.8858	0.3541	0.047*
H18B	0.7587	0.9161	0.4588	0.047*
H18C	0.6045	0.9628	0.4071	0.047*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0254 (3)	0.0223 (3)	0.0209 (3)	0.0097 (2)	0.0034 (2)	0.0019 (2)
F1	0.0876 (12)	0.0416 (9)	0.0248 (7)	0.0235 (8)	0.0082 (7)	−0.0018 (6)
O1	0.0420 (10)	0.0256 (9)	0.0233 (8)	0.0007 (7)	0.0076 (7)	−0.0027 (6)
O2	0.0279 (8)	0.0261 (8)	0.0212 (8)	0.0035 (7)	0.0090 (6)	0.0038 (6)
O3	0.0267 (8)	0.0276 (9)	0.0286 (8)	0.0001 (7)	0.0071 (7)	0.0052 (7)
O4	0.0300 (8)	0.0334 (9)	0.0232 (8)	0.0144 (7)	0.0096 (6)	0.0055 (6)
O5	0.0405 (9)	0.0229 (8)	0.0371 (9)	0.0164 (7)	0.0046 (7)	0.0044 (7)
O6	0.0216 (7)	0.0217 (8)	0.0199 (7)	0.0049 (6)	0.0032 (6)	−0.0016 (6)
O7	0.0216 (8)	0.0325 (9)	0.0329 (9)	0.0077 (7)	0.0056 (7)	−0.0022 (7)
O8	0.0252 (8)	0.0225 (8)	0.0203 (7)	0.0007 (6)	0.0004 (6)	0.0015 (6)
N1	0.0227 (9)	0.0216 (9)	0.0217 (9)	0.0069 (8)	0.0043 (7)	0.0032 (7)
N2	0.0211 (9)	0.0224 (9)	0.0186 (9)	0.0070 (8)	0.0040 (7)	0.0049 (7)
N3	0.0247 (9)	0.0261 (10)	0.0169 (9)	0.0028 (8)	0.0044 (7)	0.0040 (7)
N4	0.0259 (10)	0.0240 (10)	0.0191 (9)	0.0034 (8)	0.0038 (7)	0.0039 (7)
N5	0.0226 (10)	0.0291 (11)	0.0374 (11)	0.0090 (9)	0.0027 (8)	−0.0029 (8)
C1	0.0451 (14)	0.0327 (13)	0.0241 (12)	0.0103 (11)	0.0094 (10)	−0.0029 (10)
C2	0.0318 (12)	0.0303 (12)	0.0216 (11)	0.0106 (10)	0.0060 (9)	0.0018 (9)
C3	0.0255 (11)	0.0194 (11)	0.0240 (11)	0.0079 (9)	0.0028 (9)	0.0022 (9)
C4	0.0201 (10)	0.0211 (11)	0.0212 (11)	0.0088 (9)	0.0034 (8)	0.0062 (9)
C5	0.0217 (11)	0.0226 (11)	0.0218 (11)	0.0098 (9)	0.0061 (8)	0.0072 (9)
C6	0.0242 (11)	0.0212 (11)	0.0256 (11)	0.0042 (9)	0.0046 (9)	0.0047 (9)
C7	0.0228 (11)	0.0234 (12)	0.0231 (11)	0.0088 (10)	0.0039 (9)	0.0045 (9)
C8	0.0233 (11)	0.0186 (11)	0.0166 (10)	0.0054 (9)	0.0018 (8)	−0.0006 (8)
C9	0.0230 (11)	0.0237 (11)	0.0178 (10)	0.0059 (9)	0.0030 (8)	−0.0018 (8)
C10	0.0206 (12)	0.0335 (14)	0.0439 (14)	0.0042 (11)	0.0030 (10)	−0.0089 (11)
C11	0.0285 (13)	0.0265 (13)	0.0412 (14)	0.0001 (11)	0.0088 (10)	−0.0034 (11)
C12	0.0348 (13)	0.0212 (12)	0.0303 (12)	0.0062 (10)	0.0077 (10)	0.0018 (9)
C13	0.0267 (11)	0.0214 (11)	0.0187 (10)	0.0104 (9)	0.0063 (8)	0.0004 (8)
C14	0.0467 (14)	0.0288 (13)	0.0205 (11)	0.0157 (11)	0.0065 (10)	0.0016 (9)
C15	0.0630 (18)	0.0304 (14)	0.0261 (13)	0.0128 (12)	0.0096 (12)	0.0091 (10)
C16	0.0221 (11)	0.0171 (10)	0.0213 (11)	0.0061 (9)	0.0024 (9)	0.0063 (8)
C17	0.0206 (11)	0.0246 (11)	0.0199 (11)	0.0028 (9)	0.0026 (8)	0.0019 (9)
C18	0.0281 (12)	0.0224 (12)	0.0343 (13)	0.0002 (10)	0.0058 (10)	0.0007 (10)

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Geometric parameters (Å, º)

S1—O5	1.4242 (15)	C1—H1C	0.9800
S1—O4	1.4295 (15)	C2—H2A	0.9800
S1—N4	1.6369 (17)	C2—H2B	0.9800
S1—C8	1.774 (2)	C2—H2C	0.9800
F1—C14	1.397 (2)	C3—C6	1.389 (3)
O1—C3	1.343 (2)	C5—C6	1.379 (3)
O1—C1	1.437 (3)	C6—H6	0.9500
O2—C5	1.338 (2)	C8—C12	1.385 (3)
O2—C2	1.448 (2)	C8—C9	1.398 (3)
O3—C7	1.207 (2)	C9—C13	1.520 (3)
O6—C16	1.359 (2)	C10—C11	1.371 (3)
O6—C13	1.455 (2)	C10—H10	0.9500
O7—C16	1.197 (2)	C11—C12	1.383 (3)
O8—C17	1.412 (2)	C11—H11	0.9500
O8—C18	1.429 (2)	C12—H12	0.9500
N1—C3	1.329 (3)	C13—C14	1.522 (3)
N1—C4	1.336 (2)	C13—H13	1.0000
N2—C4	1.328 (2)	C14—C15	1.497 (3)
N2—C5	1.339 (2)	C14—H14	1.0000
N3—C7	1.388 (3)	C15—H15A	0.9800
N3—C4	1.389 (2)	C15—H15B	0.9800
N3—H3N	0.8800	C15—H15C	0.9800
N4—C7	1.386 (3)	C16—C17	1.510 (3)
N4—H4N	0.8800	C17—H17A	0.9900
N5—C10	1.337 (3)	C17—H17B	0.9900
N5—C9	1.341 (3)	C18—H18A	0.9800
C1—H1A	0.9800	C18—H18B	0.9800
C1—H1B	0.9800	C18—H18C	0.9800

O5—S1—O4	119.31 (9)	C12—C8—S1	116.68 (16)
O5—S1—N4	110.36 (9)	C9—C8—S1	123.71 (15)
O4—S1—N4	103.89 (9)	N5—C9—C8	121.03 (18)
O5—S1—C8	107.60 (9)	N5—C9—C13	113.94 (18)
O4—S1—C8	109.39 (9)	C8—C9—C13	124.95 (18)
N4—S1—C8	105.49 (9)	N5—C10—C11	124.2 (2)
C3—O1—C1	117.99 (17)	N5—C10—H10	117.9
C5—O2—C2	117.95 (16)	C11—C10—H10	117.9
C16—O6—C13	117.59 (15)	C10—C11—C12	118.0 (2)
C17—O8—C18	114.20 (16)	C10—C11—H11	121.0
C3—N1—C4	114.61 (17)	C12—C11—H11	121.0
C4—N2—C5	116.32 (17)	C11—C12—C8	118.9 (2)
C7—N3—C4	130.02 (17)	C11—C12—H12	120.5
C7—N3—H3N	115.0	C8—C12—H12	120.5
C4—N3—H3N	115.0	O6—C13—C9	105.26 (15)
C7—N4—S1	124.61 (15)	O6—C13—C14	108.51 (16)
C7—N4—H4N	117.7	C9—C13—C14	111.96 (17)
S1—N4—H4N	117.7	O6—C13—H13	110.3
C10—N5—C9	118.31 (19)	C9—C13—H13	110.3
O1—C1—H1A	109.5	C14—C13—H13	110.3
O1—C1—H1B	109.5	F1—C14—C15	108.89 (18)
H1A—C1—H1B	109.5	F1—C14—C13	105.03 (17)
O1—C1—H1C	109.5	C15—C14—C13	115.37 (19)
H1A—C1—H1C	109.5	F1—C14—H14	109.1
H1B—C1—H1C	109.5	C15—C14—H14	109.1
O2—C2—H2A	109.5	C13—C14—H14	109.1
O2—C2—H2B	109.5	C14—C15—H15A	109.5
H2A—C2—H2B	109.5	C14—C15—H15B	109.5
O2—C2—H2C	109.5	H15A—C15—H15B	109.5
H2A—C2—H2C	109.5	C14—C15—H15C	109.5
H2B—C2—H2C	109.5	H15A—C15—H15C	109.5
N1—C3—O1	119.08 (18)	H15B—C15—H15C	109.5
N1—C3—C6	124.73 (19)	O7—C16—O6	124.13 (18)
O1—C3—C6	116.20 (18)	O7—C16—C17	126.38 (18)
N2—C4—N1	126.77 (18)	O6—C16—C17	109.49 (17)
N2—C4—N3	117.95 (17)	O8—C17—C16	111.44 (17)
N1—C4—N3	115.28 (17)	O8—C17—H17A	109.3
O2—C5—N2	118.40 (17)	C16—C17—H17A	109.3
O2—C5—C6	118.68 (18)	O8—C17—H17B	109.3
N2—C5—C6	122.91 (18)	C16—C17—H17B	109.3
C5—C6—C3	114.59 (19)	H17A—C17—H17B	108.0
C5—C6—H6	122.7	O8—C18—H18A	109.5
C3—C6—H6	122.7	O8—C18—H18B	109.5
O3—C7—N4	123.77 (18)	H18A—C18—H18B	109.5
O3—C7—N3	121.97 (18)	O8—C18—H18C	109.5
N4—C7—N3	114.23 (18)	H18A—C18—H18C	109.5
C12—C8—C9	119.55 (19)	H18B—C18—H18C	109.5

O5—S1—N4—C7	−48.10 (19)	O4—S1—C8—C9	−42.99 (19)
O4—S1—N4—C7	−177.12 (16)	N4—S1—C8—C9	68.21 (18)
C8—S1—N4—C7	67.84 (19)	C10—N5—C9—C8	0.1 (3)
C4—N1—C3—O1	179.93 (18)	C10—N5—C9—C13	−176.75 (18)
C4—N1—C3—C6	0.4 (3)	C12—C8—C9—N5	−1.9 (3)
C1—O1—C3—N1	−2.3 (3)	S1—C8—C9—N5	175.19 (15)
C1—O1—C3—C6	177.23 (18)	C12—C8—C9—C13	174.60 (19)
C5—N2—C4—N1	−3.1 (3)	S1—C8—C9—C13	−8.3 (3)
C5—N2—C4—N3	177.34 (17)	C9—N5—C10—C11	2.1 (3)
C3—N1—C4—N2	2.1 (3)	N5—C10—C11—C12	−2.4 (3)
C3—N1—C4—N3	−178.32 (17)	C10—C11—C12—C8	0.5 (3)
C7—N3—C4—N2	−4.5 (3)	C9—C8—C12—C11	1.6 (3)
C7—N3—C4—N1	175.92 (19)	S1—C8—C12—C11	−175.75 (16)
C2—O2—C5—N2	4.5 (3)	C16—O6—C13—C9	137.43 (16)
C2—O2—C5—C6	−176.37 (17)	C16—O6—C13—C14	−102.57 (19)
C4—N2—C5—O2	−179.30 (17)	N5—C9—C13—O6	70.7 (2)
C4—N2—C5—C6	1.6 (3)	C8—C9—C13—O6	−106.1 (2)
O2—C5—C6—C3	−178.55 (17)	N5—C9—C13—C14	−47.0 (2)
N2—C5—C6—C3	0.6 (3)	C8—C9—C13—C14	136.2 (2)
N1—C3—C6—C5	−1.6 (3)	O6—C13—C14—F1	−174.62 (16)
O1—C3—C6—C5	178.85 (17)	C9—C13—C14—F1	−58.9 (2)
S1—N4—C7—O3	−6.7 (3)	O6—C13—C14—C15	65.5 (2)
S1—N4—C7—N3	175.33 (14)	C9—C13—C14—C15	−178.77 (19)
C4—N3—C7—O3	177.7 (2)	C13—O6—C16—O7	4.0 (3)
C4—N3—C7—N4	−4.4 (3)	C13—O6—C16—C17	−175.72 (16)
O5—S1—C8—C12	3.21 (18)	C18—O8—C17—C16	85.3 (2)
O4—S1—C8—C12	134.21 (16)	O7—C16—C17—O8	−25.1 (3)
N4—S1—C8—C12	−114.60 (16)	O6—C16—C17—O8	154.58 (15)
O5—S1—C8—C9	−173.98 (16)

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Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the N5/C8–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O8ⁱ	0.88	2.01	2.885 (2)	174
C1—H1A···O3ⁱ	0.98	2.58	3.368 (3)	137
C2—H2B···F1ⁱⁱ	0.98	2.53	3.161 (2)	122
C12—H12···O2ⁱⁱⁱ	0.95	2.42	3.229 (3)	143
C17—H17A···O5^iv	0.99	2.55	3.367 (3)	139
C1—H1B···Cg1ⁱ	0.98	2.74	3.488 (2)	134

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Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y−1, z; (iv) x, y+1, z.

Funding Statement

This work was funded by National Research Foundation of Korea grants 2015R1D1A4A01020317 and 2017R1D1A3A03000534.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc.,Madison, Wisconsin, USA.
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst B72, 171–179. [DOI] [PMC free article] [PubMed]
Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2418–o2420.
Jeon, Y., Kim, J., Kwon, E. & Kim, T. H. (2015). Acta Cryst. E71, o470–o471. [DOI] [PMC free article] [PubMed]
Kang, G., Kim, J., Kwon, E. & Kim, T. H. (2015). Acta Cryst. E71, o631–o632. [DOI] [PMC free article] [PubMed]
Kim, D. S., Koo, S. J., Lee, J. N., Hwang, K. H., Kim, T. Y., Kang, K. G., Hwang, K. S., Joe, G. H., Cho, J. H. & Kim, D. W. (2003). Congress Proceedings-BCPC International Congress: Crop Sci. & Tech 1, 87–92.
Kim, D. S., Lee, J. N., Hwang, K. H., Kang, K. G., Kim, T. Y., Koo, S. J. & Caseley, J. C. (2003). Congress Proceedings-BCPC International Congress: Crop Sci. & Tech 2, 941-946.
Kwon, E., Kim, J., Park, H. & Kim, T. H. (2016). Acta Cryst. E72, 1468–1470. [DOI] [PMC free article] [PubMed]
Lee, Y.-S., Liu, K.-H., Moon, J.-K., Ko, B. J., Choi, H., Hwang, K.-S., Kim, E. & Kim, J.-H. (2014). J. Agric. Food Chem. 62, 3057–3063. [DOI] [PubMed]
Lin, C.-H. & Liu, N.-S. (2012). Acta Cryst. E68, o1898. [DOI] [PMC free article] [PubMed]
Pan, W.-G., Zhao, Z.-D., Luo, P., Lin, C.-W. & Miao, J.-H. (2012). Z. Kristallogr. NCS, 224, 583-585.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Wu, D., Wang, X., Pang, D., Su, W. & Sun, Y. (2012). Acta Cryst. E68, o446. [DOI] [PMC free article] [PubMed]
Xia, J., Li, F., Yin, L., Yu, D. & Wu, D. (2008). Acta Cryst. E64, o632. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989017012737/hg5495sup1.cif

e-73-01439-sup1.cif^{(384.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017012737/hg5495Isup2.hkl

e-73-01439-Isup2.hkl^{(300.8KB, hkl)}

CCDC reference: 1572854

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.

[bb2] Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc.,Madison, Wisconsin, USA.

[bb17] Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst B72, 171–179. [DOI] [PMC free article] [PubMed]

[bb3] Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2418–o2420.

[bb4] Jeon, Y., Kim, J., Kwon, E. & Kim, T. H. (2015). Acta Cryst. E71, o470–o471. [DOI] [PMC free article] [PubMed]

[bb5] Kang, G., Kim, J., Kwon, E. & Kim, T. H. (2015). Acta Cryst. E71, o631–o632. [DOI] [PMC free article] [PubMed]

[bb6] Kim, D. S., Koo, S. J., Lee, J. N., Hwang, K. H., Kim, T. Y., Kang, K. G., Hwang, K. S., Joe, G. H., Cho, J. H. & Kim, D. W. (2003). Congress Proceedings-BCPC International Congress: Crop Sci. & Tech 1, 87–92.

[bb7] Kim, D. S., Lee, J. N., Hwang, K. H., Kang, K. G., Kim, T. Y., Koo, S. J. & Caseley, J. C. (2003). Congress Proceedings-BCPC International Congress: Crop Sci. & Tech 2, 941-946.

[bb8] Kwon, E., Kim, J., Park, H. & Kim, T. H. (2016). Acta Cryst. E72, 1468–1470. [DOI] [PMC free article] [PubMed]

[bb9] Lee, Y.-S., Liu, K.-H., Moon, J.-K., Ko, B. J., Choi, H., Hwang, K.-S., Kim, E. & Kim, J.-H. (2014). J. Agric. Food Chem. 62, 3057–3063. [DOI] [PubMed]

[bb10] Lin, C.-H. & Liu, N.-S. (2012). Acta Cryst. E68, o1898. [DOI] [PMC free article] [PubMed]

[bb11] Pan, W.-G., Zhao, Z.-D., Luo, P., Lin, C.-W. & Miao, J.-H. (2012). Z. Kristallogr. NCS, 224, 583-585.

[bb12] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb13] Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

[bb14] Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

[bb15] Wu, D., Wang, X., Pang, D., Su, W. & Sun, Y. (2012). Acta Cryst. E68, o446. [DOI] [PMC free article] [PubMed]

[bb16] Xia, J., Li, F., Yin, L., Yu, D. & Wu, D. (2008). Acta Cryst. E64, o632. [DOI] [PMC free article] [PubMed]

PERMALINK

Crystal structure of flucetosulfuron

Hyunjin Park

Jineun Kim

Eunjin Kwon

Tae Ho Kim

Abstract

Chemical context

Structural commentary

Figure 1.