The herbicide triflusulfuron-meth­yl

Mereiter, K.

doi:10.1107/S1600536811023166

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1778-o1779

doi:10.1107/S1600536811023166

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The herbicide triflusulfuron-methyl

Kurt Mereiter ^a ^*

^aInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
^*Correspondence e-mail: kurt.mereiter@tuwien.ac.at

(Received 11 June 2011; accepted 14 June 2011; online 22 June 2011)

The molecule of the title compound [systematic name: methyl 2-({[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)-3-methylbenzoate], C₁₇H₁₉F₃N₆O₆S, features a nearly planar (r.m.s. deviation = 0.098 Å) dimethylaminotriazinyl-urea group with a short intramolecular N—H⋯N hydrogen bond to a triazine N atom. An intramolecular dipole–dipole interaction between the sulfamide and carboxylate groups, with O_s⋯C_c = 2.800 (1) Å and N_s⋯O_c = 2.835 (1) Å, controls the orientation of the methylbenzoate group and the shape of the molecule. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen bonding, C—H⋯X (X = N,O) interactions and arene π–π stacking.

Related literature

For general information on the synthesis and herbicidal properties of the title compound, see: EFSA (2008 ); Moon (1989 ); Peeples et al. (1991 ); Wittenbach et al. (1994 ). For the inhibition mechanism of sulfonylurea herbicides on acetohydroxy acid syntheases, see: Duggleby et al. (2008 ); McCourt et al. (2005 ). For the crystal structures of related sulfonylurea compounds, see: Ma, Wang et al. (2003 ); Ma, Li et al. (2003 ); Wang et al. (2004 ); Sorokin et al. (1993 ); Liu et al. (2008 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₉F₃N₆O₆S
M_r = 492.44
Monoclinic, C 2/c
a = 16.7107 (11) Å
b = 15.6406 (11) Å
c = 17.1875 (12) Å
β = 107.035 (1)°
V = 4295.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.55 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.84, T_max = 0.94
31010 measured reflections
6217 independent reflections
5708 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.102
S = 1.07
6217 reflections
302 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N5	0.88	1.95	2.6410 (13)	135
N2—H2N⋯N3ⁱ	0.88	2.03	2.8998 (12)	172
C9—H9A⋯O5	0.98	2.42	3.2253 (16)	139
C14—H14B⋯O3	0.98	2.59	3.4363 (16)	145
C14—H14C⋯O5ⁱⁱ	0.98	2.42	3.2637 (14)	143
C16—H16A⋯O2ⁱⁱⁱ	0.99	2.55	3.4209 (14)	147
C16—H16B⋯O1^iv	0.99	2.32	3.2325 (14)	153
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT, SADABS and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811023166/gk2384sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023166/gk2384Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023166/gk2384Isup3.cml

checkCIF report

Comment top

Triflusulfuron-methyl, methyl 2-[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl]-3-methylbenzoate, (I), is the methyl ester of Triflusulfuron. Both substances are triazinylsulfonylurea herbicides, a subclass of sulfonylurea herbicides. These substances are efficient inhibitors of acetohydroxyacid synthase (AHAS), which impairs the synthesis of the branched-chain amino acids valine, leucine and isoleucine in plants leading to the cessation of cell division and subsequent growth processes (EFSA, 2008). Triflusulfuron-methyl is in use as a post-emergence herbicide in crop protection of sugar and fodder beet in order to control various annual grasses and broad–leaved weeds like fools parsley, mayweeds, brassica species, or small nettle (Moon, 1989; Peeples et al., 1991; Wittenbach et al., 1994). Trade names of the originator DuPont^TM (Moon, 1989) for formulations of (I) are UpBeet in the USA and Canada, and Debut or Safari in Europe. For mammalians, the toxicity of Triflusulfuron-methyl is comparatively low whereas it is high for aquatic organisms (EFSA, 2008). In view of the actual importance of this substance a crystal structure determination was carried out and is presented here.

A view of the asymmetric unit of the structure is presented in Fig. 1. Bond lengths and angles in the molecule exhibit normal values (Allen et al., 1987) and are in good agreement with the few related crystal structures, which have been determined so far with comparable accuracy [refcodes RACCOO (Ma, Wang et al., 2003), XUYTUG (Ma, Li et al., 2003), NAFWAT (Wang et al., 2004) and YUZHUW (Sorokin et al., 1993); Cambridge Structural Database, Version 5.31, with Aug. 2010 updates; Allen, 2002]. The molecule of the title compound can be divided into three approximately planar parts: (i) the triazinylsulfonylurea group including the triazine substituents N(CH₃)₂ and OCH₂CF₃ comprising the 18 atoms S1, O2, O5, O6, N1 to N6, and C10 to C17 with a r.m.s. deviation from planarity of 0.098 Å; (ii) the methylphenyl group with a r.m.s. deviation from planarity of 0.011 Å; and (iii) the methylcarboxylate group with a r.m.s. deviation from planarity of 0.002 Å. The interplanar angle is 75.26 (2)° between (i) and (ii), and 48.07 (6)° between (ii) and (iii). The mutual orienations of these three parts and the shape of the entire molecule are controlled by two remarkable intramolecular interactions. Firstly, by a short and strong internal hydrogen bond N1—H1n···N5 with N1···N5 = 2.641 (1) Å, where H1n is the most acidic hydrogen atom of the compound and N5 is a triazine nitrogen as the acceptor (Fig. 1). Secondly, by an intramolecular dipole-dipole interaction between the sulfamoyl and the carboxylate group with the very short contact distances O2···C7 = 2.800 (1) Å and O3···N1 = 2.835 (1) Å (Fig. 1). These interactions are characteristic also for other triazinyl- and pyrimidinyl-sulfonylurea compounds, e.g. for RACCOO (Ma, Wang et al., 2003) where the corresponding distances are N(H)···N = 2.690 Å, O···C = 2.823 Å, and O···N = 3.198 Å, respectively. As the result the stereochemistry and shape of the molecule cores of all these compounds is in crystalline state remarkably uniform. Interestingly this stereochemistry changes drastically when the molecules enter the herbicide binding site of acetohydroxyacid synthases (AHAS): There molecules like (I) convert by ~180°-rotations about the bonds C11—N2 and N2—C10, which opens the intramolecular hydrogen bond N1—H1n···N5, makes both NH groups to be approximately parallel and exo-oriented toward hydrogen bond acceptors like H₂O, and brings O5, N3, and O6 closely together for hydrogen bond interactions with the guanidine terminus of an arginine in the herbicide pocket of AHAS enzymes (McCourt et al., 2005; Duggleby et al., 2008). Such conversion also takes place under concomitant deprotonation of N1 when a triazinyl- or pyrimidinyl-sulfonylurea compound chelates a metal atom with the urea oxygen (O becomes formally anionic by NH-deprotonation) and a triazine/pyrimidine nitrogen, e.g. in the Cu complex MOGTIM (Liu et al., 2008).

Further hydrogen bond-like interactions in (I) are listed in Table 1. The most important of them, apart from N1—H1n···N5, is the intermolecular bond N2—H2n···N3ⁱ, two of which link a pair of molecules related by a twofold symmetry axis (Fig. 1). In the crystal lattice these hydrogen bonded pairs interact then by π-π-stacking between pairs of inversion related and mutually slipped dimethylamino-triazine groups with a C13—C13(1 - x,1 - y,1 - z) distance of 3.460 (2) Å (ring-ring perpendicular distance 3.420 Å, ring-ring slippage 2.743 Å) and by weaker π-π-stacking between inversion related pairs of benzene rings (perpendicular distance 3.587 Å, ring-ring slippage 1.002 Å). Fig. 2 exemplifies a part of the crystal lattice with N—H···N hydrogen bonds and triazine π-π- interactions. A packing diagram of the structure is depicted in Fig. 3.

Related literature top

For general information on the synthesis and herbicidal properties of the title compound, see: EFSA (2008); Moon (1989); Peeples et al. (1991); Wittenbach et al. (1994). For the inhibition mechanism of sulfonylurea herbicides on acetohydroxy acid syntheases, see: Duggleby et al. (2008); McCourt et al. (2005). For the crystal structures of related sulfonylurea compounds, see: Ma, Wang et al. (2003); Ma, Li et al. (2003); Wang et al. (2004); Sorokin et al. (1993); Liu et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

A sample of (I) was obtained from Sigma-Aldrich. It was recrystallized from methanol by room temperature evaporation to furnish colourless prisms suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT, SADABS and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. Hydrogen bonds are drawn as dashed red lines. Symmetry code i: -x + 1, y, -z + 3/2. Intramolecular interactions are N1···N5 = 2.641 (1) Å, O2···C7 = 2.800 (1) Å, and O3···N1 = 2.835 (1) Å.
	Fig. 2. View of the crystal structure of (I) showing N—H···N hydrogen bonds as dashed red lines and π-π stacking interactions between dimethylamino-triazine groups as orange lines. C-bonded H-atoms omitted for clarity.
	Fig. 3. Packing diagram of (I) in a view down the c-axis, i.e. approximately along the intermolecular hydrogen bonds N2—H2n···N3. H-atoms omitted for clarity.

Methyl 2-({[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2- yl]carbamoyl}sulfamoyl)-3-methylbenzoate top

Crystal data top

C₁₇H₁₉F₃N₆O₆S	F(000) = 2032
M_r = 492.44	D_x = 1.523 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.7107 (11) Å	Cell parameters from 9962 reflections
b = 15.6406 (11) Å	θ = 2.6–30.5°
c = 17.1875 (12) Å	µ = 0.23 mm⁻¹
β = 107.035 (1)°	T = 100 K
V = 4295.1 (5) Å³	Block, colourless
Z = 8	0.55 × 0.35 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6217 independent reflections
Radiation source: fine-focus sealed tube	5708 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→23
T_min = 0.84, T_max = 0.94	k = −22→22
31010 measured reflections	l = −23→23

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0559P)² + 3.028P] where P = (F_o² + 2F_c²)/3
6217 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₇H₁₉F₃N₆O₆S	V = 4295.1 (5) Å³
M_r = 492.44	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.7107 (11) Å	µ = 0.23 mm⁻¹
b = 15.6406 (11) Å	T = 100 K
c = 17.1875 (12) Å	0.55 × 0.35 × 0.30 mm
β = 107.035 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6217 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5708 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.94	R_int = 0.024
31010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	Δρ_max = 0.50 e Å⁻³
6217 reflections	Δρ_min = −0.49 e Å⁻³
302 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.196829 (15)	0.535633 (16)	0.521723 (15)	0.01859 (7)
O1	0.19376 (6)	0.62050 (5)	0.55125 (6)	0.02835 (18)
O2	0.18217 (5)	0.52321 (5)	0.43604 (5)	0.02233 (16)
O3	0.22779 (6)	0.34464 (6)	0.47823 (6)	0.02816 (18)
O4	0.09973 (6)	0.31848 (6)	0.39337 (6)	0.03011 (19)
O5	0.29214 (5)	0.50520 (6)	0.69463 (5)	0.02743 (18)
O6	0.65207 (5)	0.33795 (5)	0.66348 (5)	0.02148 (16)
N1	0.29218 (5)	0.49756 (6)	0.56180 (5)	0.01930 (17)
H1N	0.3228	0.4857	0.5294	0.023*
N2	0.40259 (5)	0.44268 (6)	0.66704 (5)	0.01867 (17)
H2N	0.4227	0.4320	0.7194	0.022*
N3	0.52875 (5)	0.38975 (6)	0.66484 (5)	0.01831 (17)
N4	0.55747 (6)	0.36370 (6)	0.53872 (5)	0.01880 (17)
N5	0.42372 (5)	0.41857 (6)	0.54018 (5)	0.01753 (16)
N6	0.45192 (6)	0.39316 (6)	0.41973 (5)	0.02194 (18)
C1	0.12686 (6)	0.46904 (7)	0.55453 (7)	0.02002 (19)
C2	0.10617 (7)	0.38937 (7)	0.51509 (7)	0.0220 (2)
C3	0.04287 (8)	0.34016 (8)	0.52991 (8)	0.0295 (2)
H3	0.0281	0.2869	0.5030	0.035*
C4	0.00129 (8)	0.36899 (9)	0.58398 (9)	0.0323 (3)
H4	−0.0426	0.3358	0.5934	0.039*
C5	0.02355 (7)	0.44542 (9)	0.62381 (8)	0.0305 (3)
H5	−0.0049	0.4634	0.6614	0.037*
C6	0.08655 (7)	0.49787 (8)	0.61108 (7)	0.0252 (2)
C7	0.15278 (7)	0.35064 (7)	0.46116 (7)	0.0229 (2)
C8	0.13986 (9)	0.27562 (9)	0.34038 (9)	0.0349 (3)
H8A	0.0972	0.2494	0.2949	0.052*
H8B	0.1774	0.2312	0.3710	0.052*
H8C	0.1722	0.3172	0.3193	0.052*
C9	0.10498 (8)	0.57997 (10)	0.65897 (9)	0.0352 (3)
H9A	0.1656	0.5858	0.6835	0.053*
H9B	0.0773	0.5791	0.7020	0.053*
H9C	0.0841	0.6285	0.6226	0.053*
C10	0.32549 (6)	0.48361 (7)	0.64409 (6)	0.01966 (19)
C11	0.45251 (6)	0.41618 (6)	0.62069 (6)	0.01614 (18)
C12	0.57646 (6)	0.36447 (6)	0.61875 (6)	0.01739 (18)
C13	0.47864 (7)	0.39181 (6)	0.50082 (6)	0.01759 (18)
C14	0.36494 (8)	0.41607 (8)	0.37767 (7)	0.0259 (2)
H14A	0.3530	0.4731	0.3951	0.039*
H14B	0.3273	0.3743	0.3911	0.039*
H14C	0.3564	0.4161	0.3188	0.039*
C15	0.50356 (9)	0.36299 (8)	0.37022 (7)	0.0279 (2)
H15A	0.5611	0.3547	0.4048	0.042*
H15B	0.5030	0.4054	0.3281	0.042*
H15C	0.4813	0.3086	0.3445	0.042*
C16	0.71016 (7)	0.31386 (7)	0.62056 (7)	0.0224 (2)
H16A	0.7187	0.3614	0.5858	0.027*
H16B	0.6896	0.2633	0.5859	0.027*
C17	0.78997 (8)	0.29349 (10)	0.68535 (9)	0.0334 (3)
F1	0.84761 (5)	0.26665 (7)	0.65023 (7)	0.0484 (2)
F2	0.78026 (6)	0.23027 (8)	0.73382 (7)	0.0546 (3)
F3	0.82179 (6)	0.36048 (8)	0.73076 (7)	0.0570 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01670 (12)	0.01668 (12)	0.02069 (13)	0.00019 (8)	0.00281 (9)	0.00071 (8)
O1	0.0256 (4)	0.0188 (4)	0.0389 (5)	0.0006 (3)	0.0068 (3)	−0.0046 (3)
O2	0.0207 (4)	0.0242 (4)	0.0199 (4)	0.0001 (3)	0.0026 (3)	0.0051 (3)
O3	0.0252 (4)	0.0237 (4)	0.0338 (5)	0.0012 (3)	0.0060 (3)	−0.0034 (3)
O4	0.0294 (4)	0.0285 (4)	0.0293 (4)	−0.0035 (3)	0.0038 (3)	−0.0060 (3)
O5	0.0214 (4)	0.0398 (5)	0.0203 (4)	0.0045 (3)	0.0048 (3)	−0.0065 (3)
O6	0.0160 (3)	0.0298 (4)	0.0192 (3)	0.0026 (3)	0.0060 (3)	0.0009 (3)
N1	0.0155 (4)	0.0234 (4)	0.0175 (4)	0.0012 (3)	0.0025 (3)	−0.0011 (3)
N2	0.0165 (4)	0.0263 (4)	0.0124 (3)	0.0017 (3)	0.0028 (3)	−0.0007 (3)
N3	0.0153 (4)	0.0251 (4)	0.0139 (4)	0.0002 (3)	0.0033 (3)	0.0004 (3)
N4	0.0213 (4)	0.0197 (4)	0.0164 (4)	−0.0022 (3)	0.0070 (3)	−0.0011 (3)
N5	0.0191 (4)	0.0192 (4)	0.0130 (4)	−0.0012 (3)	0.0028 (3)	−0.0003 (3)
N6	0.0271 (4)	0.0253 (4)	0.0133 (4)	−0.0033 (3)	0.0058 (3)	−0.0003 (3)
C1	0.0165 (4)	0.0220 (5)	0.0199 (4)	0.0002 (3)	0.0027 (3)	0.0032 (4)
C2	0.0202 (5)	0.0199 (5)	0.0240 (5)	0.0000 (4)	0.0036 (4)	0.0040 (4)
C3	0.0245 (5)	0.0237 (5)	0.0385 (6)	−0.0032 (4)	0.0062 (5)	0.0078 (5)
C4	0.0222 (5)	0.0360 (6)	0.0389 (7)	0.0002 (5)	0.0092 (5)	0.0161 (5)
C5	0.0203 (5)	0.0442 (7)	0.0276 (6)	0.0058 (5)	0.0080 (4)	0.0104 (5)
C6	0.0185 (5)	0.0337 (6)	0.0222 (5)	0.0036 (4)	0.0038 (4)	0.0017 (4)
C7	0.0252 (5)	0.0152 (4)	0.0266 (5)	−0.0019 (4)	0.0048 (4)	0.0014 (4)
C8	0.0402 (7)	0.0314 (6)	0.0322 (6)	−0.0034 (5)	0.0091 (5)	−0.0095 (5)
C9	0.0251 (6)	0.0480 (8)	0.0327 (6)	0.0036 (5)	0.0089 (5)	−0.0129 (6)
C10	0.0163 (4)	0.0229 (5)	0.0180 (4)	−0.0014 (4)	0.0023 (3)	−0.0032 (4)
C11	0.0156 (4)	0.0177 (4)	0.0143 (4)	−0.0022 (3)	0.0031 (3)	−0.0003 (3)
C12	0.0169 (4)	0.0181 (4)	0.0172 (4)	−0.0022 (3)	0.0052 (3)	0.0001 (3)
C13	0.0222 (5)	0.0159 (4)	0.0147 (4)	−0.0042 (3)	0.0054 (3)	−0.0005 (3)
C14	0.0293 (5)	0.0301 (5)	0.0143 (4)	−0.0027 (4)	0.0000 (4)	0.0014 (4)
C15	0.0381 (6)	0.0310 (6)	0.0176 (5)	−0.0032 (5)	0.0131 (4)	−0.0024 (4)
C16	0.0195 (4)	0.0237 (5)	0.0270 (5)	0.0007 (4)	0.0118 (4)	0.0007 (4)
C17	0.0203 (5)	0.0438 (7)	0.0387 (7)	0.0052 (5)	0.0127 (5)	0.0088 (5)
F1	0.0268 (4)	0.0632 (6)	0.0641 (6)	0.0147 (4)	0.0270 (4)	0.0148 (5)
F2	0.0356 (5)	0.0737 (7)	0.0595 (6)	0.0213 (5)	0.0215 (4)	0.0405 (5)
F3	0.0273 (4)	0.0810 (8)	0.0545 (6)	−0.0069 (4)	−0.0011 (4)	−0.0191 (5)

Geometric parameters (Å, º) top

S1—O1	1.4274 (9)	C2—C7	1.5020 (16)
S1—O2	1.4337 (8)	C3—C4	1.389 (2)
S1—N1	1.6507 (9)	C3—H3	0.9500
S1—C1	1.7765 (11)	C4—C5	1.374 (2)
O3—C7	1.2044 (15)	C4—H4	0.9500
O4—C7	1.3385 (14)	C5—C6	1.4016 (17)
O4—C8	1.4444 (16)	C5—H5	0.9500
O5—C10	1.2094 (13)	C6—C9	1.5076 (19)
O6—C12	1.3381 (12)	C8—H8A	0.9800
O6—C16	1.4311 (12)	C8—H8B	0.9800
N1—C10	1.3771 (13)	C8—H8C	0.9800
N1—H1N	0.8800	C9—H9A	0.9800
N2—C11	1.3753 (13)	C9—H9B	0.9800
N2—C10	1.3884 (13)	C9—H9C	0.9800
N2—H2N	0.8800	C14—H14A	0.9800
N3—C12	1.3378 (13)	C14—H14B	0.9800
N3—C11	1.3429 (12)	C14—H14C	0.9800
N4—C12	1.3179 (13)	C15—H15A	0.9800
N4—C13	1.3602 (14)	C15—H15B	0.9800
N5—C11	1.3258 (12)	C15—H15C	0.9800
N5—C13	1.3561 (13)	C16—C17	1.5000 (17)
N6—C13	1.3333 (13)	C16—H16A	0.9900
N6—C15	1.4566 (15)	C16—H16B	0.9900
N6—C14	1.4656 (15)	C17—F3	1.3216 (19)
C1—C6	1.4090 (16)	C17—F2	1.3332 (16)
C1—C2	1.4122 (15)	C17—F1	1.3449 (15)
C2—C3	1.3906 (16)

O1—S1—O2	118.56 (5)	H8A—C8—H8C	109.5
O1—S1—N1	108.54 (5)	H8B—C8—H8C	109.5
O2—S1—N1	103.49 (5)	C6—C9—H9A	109.5
O1—S1—C1	109.68 (5)	C6—C9—H9B	109.5
O2—S1—C1	108.44 (5)	H9A—C9—H9B	109.5
N1—S1—C1	107.50 (5)	C6—C9—H9C	109.5
C7—O4—C8	114.32 (10)	H9A—C9—H9C	109.5
C12—O6—C16	117.02 (8)	H9B—C9—H9C	109.5
C10—N1—S1	122.42 (8)	O5—C10—N1	124.11 (10)
C10—N1—H1N	118.8	O5—C10—N2	120.60 (10)
S1—N1—H1N	118.8	N1—C10—N2	115.29 (9)
C11—N2—C10	130.10 (9)	N5—C11—N3	126.34 (9)
C11—N2—H2N	114.9	N5—C11—N2	120.00 (9)
C10—N2—H2N	114.9	N3—C11—N2	113.67 (8)
C12—N3—C11	112.81 (8)	N4—C12—N3	128.15 (9)
C12—N4—C13	113.58 (9)	N4—C12—O6	119.67 (9)
C11—N5—C13	114.85 (9)	N3—C12—O6	112.18 (9)
C13—N6—C15	122.09 (10)	N6—C13—N5	116.63 (9)
C13—N6—C14	119.97 (9)	N6—C13—N4	119.11 (9)
C15—N6—C14	117.57 (9)	N5—C13—N4	124.26 (9)
C6—C1—C2	120.93 (10)	N6—C14—H14A	109.5
C6—C1—S1	121.56 (9)	N6—C14—H14B	109.5
C2—C1—S1	117.16 (8)	H14A—C14—H14B	109.5
C3—C2—C1	119.53 (11)	N6—C14—H14C	109.5
C3—C2—C7	116.72 (10)	H14A—C14—H14C	109.5
C1—C2—C7	123.62 (10)	H14B—C14—H14C	109.5
C4—C3—C2	119.96 (12)	N6—C15—H15A	109.5
C4—C3—H3	120.0	N6—C15—H15B	109.5
C2—C3—H3	120.0	H15A—C15—H15B	109.5
C5—C4—C3	120.04 (11)	N6—C15—H15C	109.5
C5—C4—H4	120.0	H15A—C15—H15C	109.5
C3—C4—H4	120.0	H15B—C15—H15C	109.5
C4—C5—C6	122.53 (12)	O6—C16—C17	105.26 (9)
C4—C5—H5	118.7	O6—C16—H16A	110.7
C6—C5—H5	118.7	C17—C16—H16A	110.7
C5—C6—C1	116.95 (11)	O6—C16—H16B	110.7
C5—C6—C9	117.13 (11)	C17—C16—H16B	110.7
C1—C6—C9	125.92 (11)	H16A—C16—H16B	108.8
O3—C7—O4	124.01 (11)	F3—C17—F2	108.69 (13)
O3—C7—C2	124.89 (11)	F3—C17—F1	107.18 (11)
O4—C7—C2	110.97 (10)	F2—C17—F1	106.45 (11)
O4—C8—H8A	109.5	F3—C17—C16	112.73 (12)
O4—C8—H8B	109.5	F2—C17—C16	112.14 (11)
H8A—C8—H8B	109.5	F1—C17—C16	109.34 (11)
O4—C8—H8C	109.5

O1—S1—N1—C10	64.66 (10)	S1—N1—C10—O5	−7.42 (16)
O2—S1—N1—C10	−168.53 (9)	S1—N1—C10—N2	173.18 (8)
C1—S1—N1—C10	−53.90 (10)	C11—N2—C10—O5	−177.04 (11)
O1—S1—C1—C6	−8.55 (11)	C11—N2—C10—N1	2.38 (16)
O2—S1—C1—C6	−139.44 (9)	C13—N5—C11—N3	−0.51 (15)
N1—S1—C1—C6	109.28 (9)	C13—N5—C11—N2	179.32 (9)
O1—S1—C1—C2	164.73 (8)	C12—N3—C11—N5	0.02 (15)
O2—S1—C1—C2	33.84 (10)	C12—N3—C11—N2	−179.81 (9)
N1—S1—C1—C2	−77.44 (9)	C10—N2—C11—N5	−8.96 (17)
C6—C1—C2—C3	2.50 (16)	C10—N2—C11—N3	170.89 (10)
S1—C1—C2—C3	−170.82 (9)	C13—N4—C12—N3	−0.72 (15)
C6—C1—C2—C7	−173.24 (10)	C13—N4—C12—O6	179.68 (9)
S1—C1—C2—C7	13.44 (14)	C11—N3—C12—N4	0.66 (15)
C1—C2—C3—C4	−0.85 (17)	C11—N3—C12—O6	−179.72 (9)
C7—C2—C3—C4	175.18 (11)	C16—O6—C12—N4	3.04 (14)
C2—C3—C4—C5	−1.03 (19)	C16—O6—C12—N3	−176.62 (9)
C3—C4—C5—C6	1.33 (19)	C15—N6—C13—N5	−177.58 (10)
C4—C5—C6—C1	0.28 (17)	C14—N6—C13—N5	−4.83 (14)
C4—C5—C6—C9	−179.79 (12)	C15—N6—C13—N4	1.92 (15)
C2—C1—C6—C5	−2.19 (16)	C14—N6—C13—N4	174.67 (9)
S1—C1—C6—C5	170.84 (9)	C11—N5—C13—N6	179.90 (9)
C2—C1—C6—C9	177.89 (11)	C11—N5—C13—N4	0.43 (14)
S1—C1—C6—C9	−9.08 (16)	C12—N4—C13—N6	−179.33 (9)
C8—O4—C7—O3	−0.53 (17)	C12—N4—C13—N5	0.12 (14)
C8—O4—C7—C2	−176.61 (10)	C12—O6—C16—C17	176.05 (10)
C3—C2—C7—O3	−127.73 (13)	O6—C16—C17—F3	−63.38 (13)
C1—C2—C7—O3	48.12 (17)	O6—C16—C17—F2	59.68 (14)
C3—C2—C7—O4	48.31 (14)	O6—C16—C17—F1	177.50 (10)
C1—C2—C7—O4	−135.84 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5	0.88	1.95	2.6410 (13)	135
N2—H2N···N3ⁱ	0.88	2.03	2.8998 (12)	172
C9—H9A···O5	0.98	2.42	3.2253 (16)	139
C14—H14B···O3	0.98	2.59	3.4363 (16)	145
C14—H14C···O5ⁱⁱ	0.98	2.42	3.2637 (14)	143
C15—H15A···N4	0.98	2.33	2.7695 (15)	107
C16—H16A···O2ⁱⁱⁱ	0.99	2.55	3.4209 (14)	147
C16—H16B···O1^iv	0.99	2.32	3.2325 (14)	153

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉F₃N₆O₆S
M_r	492.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	16.7107 (11), 15.6406 (11), 17.1875 (12)
β (°)	107.035 (1)
V (Å³)	4295.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.55 × 0.35 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.84, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	31010, 6217, 5708
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 1.07
No. of reflections	6217
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.49

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SAINT, SADABS and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5	0.88	1.95	2.6410 (13)	135
N2—H2N···N3ⁱ	0.88	2.03	2.8998 (12)	172
C9—H9A···O5	0.98	2.42	3.2253 (16)	139
C14—H14B···O3	0.98	2.59	3.4363 (16)	145
C14—H14C···O5ⁱⁱ	0.98	2.42	3.2637 (14)	143
C16—H16A···O2ⁱⁱⁱ	0.99	2.55	3.4209 (14)	147
C16—H16B···O1^iv	0.99	2.32	3.2325 (14)	153

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, y−1/2, z.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duggleby, R. G., McCourt, J. A. & Guddat, L. W. (2008). Plant Phys. Biochem. 46, 309–324. CrossRef CAS Google Scholar
EFSA (2008). European Food Safety Authority Scientific Report 2008, Vol. 195, pp. 1–115. Conclusion on the peer review of triflusulfuron. www.efsa.europa.eu/en/efsajournal/pub/195r.html. Google Scholar
Liu, Q.-X., Wu, X.-M., Liu, S.-W., Song, H.-B., Wang, X.-G. & Guo, J.-H. (2008). J. Coord. Chem. 61, 2990–2998. CrossRef CAS Google Scholar
Ma, N., Li, Z.-M., Wang, J.-G. & Song, H.-B. (2003). Acta Cryst. E59, o275–o276. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, N., Wang, B., Wang, J., Song, H., Wang, S. & Li, Z. (2003). Acta Cryst. E59, o438–o440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
McCourt, J. A., Pang, S. S., Guddat, L. W. & Duggleby, R. G. (2005). Biochemistry, 44, 2330–2338. Web of Science CrossRef PubMed CAS Google Scholar
Moon, M. P. (1989). WO Patent 8909214 A1. Google Scholar
Peeples, K. A., Moon, M. P., Lichtner, F. T., Wittenbach, V. A., Carski, T. H., Woodward, M. D., Graham, K. & Reinke, H. (1991). Weeds, 2, 25–30. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sorokin, V. I., Golosov, S. N., Kornilov, A. N., Yufit, D. S., Struchkov, Yu. T. & Drozd, V. N. (1993). Khim. Get. Soedin. SSSR (Russ.) (Chem. Heterocycl. Compd), pp. 1670–1675. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, B.-L., Ma, N., Wang, J.-G., Ma, Y., Li, Z.-M. & Leng, X.-B. (2004). Jiegou Huaxue, 23, 783–787. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wittenbach, V. A., Koeppe, M. K., Lichtner, F. T., Zimmerman, W. T. & Reiser, R. W. (1994). Pestic. Biochem. Physiol. 49, 72–81. CrossRef CAS Web of Science Google Scholar

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Volume 67| Part 7| July 2011| Pages o1778-o1779

doi:10.1107/S1600536811023166

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