The herbicide flumetsulam as the acetonitrile solvate

In the crystal structure of the title compound [systematic name: N-(2,6-difluoro­phen­yl)-5-meth­yl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide acetonitrile solvate], C₁₂H₉F₂N₅O₂S·C₂H₃N, the planar bicyclic triazolopyrimidine system is bound to the 2,6-difluoro­benzene group via an SO₂–NH bridge, the C—S—N—C torsion angle being −77.85 (18)°; the dihedral angle formed by the bicyclic triazolopyrimidine system and the benzene ring is 128.0 (2)°. N—H...N bonds link the mol­ecules into infinite chains running along the a axis of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.134
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C12H9F2N5O2S·C2H3N	Z = 2
Mr = 366.36	F(000) = 376
Triclinic, P1	Dx = 1.532 Mg m^−3
a = 6.9505 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6096 (7) Å	Cell parameters from 2570 reflections
c = 15.2250 (15) Å	θ = 2.7–28.0°
α = 95.985 (2)°	µ = 0.25 mm^−1
β = 96.095 (2)°	T = 293 K
γ = 93.712 (2)°	Block, yellow
V = 794.00 (13) Å^3	0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3042 independent reflections
Radiation source: fine-focus sealed tube	2784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 26.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −8→7
Tmin = 0.907, Tmax = 0.952	k = −9→8
4334 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0773P)^2 + 0.2204P] where P = (Fo^2 + 2Fc^2)/3
3042 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.13911 (7)	1.22340 (6)	0.75542 (3)	0.03707 (18)
N4	0.4862 (2)	0.8758 (2)	0.66009 (11)	0.0385 (4)
O1	1.0692 (2)	1.33139 (19)	0.82492 (10)	0.0456 (4)
N5	0.7713 (2)	0.9400 (2)	0.59166 (10)	0.0350 (4)
N1	1.2800 (3)	1.0862 (2)	0.79921 (12)	0.0391 (4)
F1	1.3457 (2)	1.26908 (19)	0.96952 (10)	0.0641 (4)
N3	0.7710 (2)	1.0535 (2)	0.73143 (11)	0.0384 (4)
C12	0.6665 (3)	0.9542 (3)	0.66344 (12)	0.0346 (4)
N2	0.9468 (2)	1.0328 (2)	0.61198 (11)	0.0386 (4)
F2	1.1470 (3)	0.7389 (2)	0.79060 (10)	0.0714 (5)
C6	1.2434 (3)	1.0069 (3)	0.87674 (13)	0.0360 (4)
O2	1.2425 (2)	1.2973 (2)	0.69004 (10)	0.0515 (4)
C10	0.4169 (3)	0.7768 (3)	0.58488 (14)	0.0383 (4)
C7	0.9357 (3)	1.0950 (3)	0.69595 (13)	0.0349 (4)
C1	1.2814 (3)	1.0973 (3)	0.96111 (14)	0.0436 (5)
C8	0.7019 (3)	0.8415 (3)	0.51366 (13)	0.0417 (5)
H8	0.7735	0.8320	0.4654	0.050*
C9	0.5234 (3)	0.7585 (3)	0.51023 (13)	0.0415 (5)
H9	0.4697	0.6886	0.4586	0.050*
C2	1.2581 (3)	1.0158 (4)	1.03614 (15)	0.0548 (6)
H2	1.2824	1.0802	1.0921	0.066*
C3	1.1991 (4)	0.8398 (4)	1.02799 (17)	0.0591 (7)
H3	1.1837	0.7846	1.0788	0.071*
C5	1.1830 (3)	0.8289 (3)	0.87223 (15)	0.0453 (5)
C4	1.1620 (4)	0.7428 (4)	0.94585 (19)	0.0577 (6)
H4	1.1239	0.6223	0.9404	0.069*
C11	0.2210 (3)	0.6820 (3)	0.57936 (17)	0.0506 (6)
H11A	0.2343	0.5615	0.5909	0.076*
H11B	0.1543	0.6838	0.5210	0.076*
H11C	0.1482	0.7396	0.6227	0.076*
C14	0.7081 (4)	0.5129 (4)	0.7242 (2)	0.0657 (8)
N6	0.7632 (5)	0.5092 (4)	0.6565 (2)	0.0926 (9)
C13	0.6374 (5)	0.5117 (5)	0.8096 (2)	0.0864 (10)
H13A	0.5697	0.3990	0.8129	0.130*
H13B	0.5506	0.6038	0.8174	0.130*
H13C	0.7448	0.5316	0.8556	0.130*
H1	1.338 (4)	1.029 (3)	0.7618 (17)	0.048 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0418 (3)	0.0374 (3)	0.0321 (3)	−0.0019 (2)	0.0080 (2)	0.0035 (2)
N4	0.0378 (9)	0.0420 (9)	0.0367 (9)	0.0014 (7)	0.0109 (7)	0.0026 (7)
O1	0.0541 (9)	0.0406 (8)	0.0411 (8)	0.0059 (7)	0.0067 (6)	−0.0027 (6)
N5	0.0370 (8)	0.0411 (9)	0.0281 (8)	0.0027 (7)	0.0090 (6)	0.0033 (7)
N1	0.0389 (9)	0.0447 (10)	0.0349 (9)	0.0047 (7)	0.0113 (7)	0.0024 (7)
F1	0.0738 (10)	0.0575 (9)	0.0534 (8)	−0.0026 (7)	−0.0052 (7)	−0.0119 (7)
N3	0.0409 (9)	0.0436 (9)	0.0313 (8)	0.0007 (7)	0.0111 (7)	0.0011 (7)
C12	0.0390 (10)	0.0361 (10)	0.0309 (9)	0.0065 (8)	0.0112 (8)	0.0040 (8)
N2	0.0391 (9)	0.0449 (10)	0.0325 (8)	−0.0006 (7)	0.0108 (7)	0.0028 (7)
F2	0.1063 (13)	0.0507 (8)	0.0521 (9)	−0.0128 (8)	0.0100 (8)	−0.0077 (7)
C6	0.0306 (9)	0.0443 (11)	0.0339 (10)	0.0055 (8)	0.0063 (7)	0.0047 (8)
O2	0.0564 (9)	0.0552 (10)	0.0438 (9)	−0.0125 (7)	0.0118 (7)	0.0133 (7)
C10	0.0402 (10)	0.0349 (10)	0.0406 (11)	0.0049 (8)	0.0068 (8)	0.0050 (8)
C7	0.0398 (10)	0.0360 (10)	0.0300 (9)	0.0025 (8)	0.0087 (8)	0.0049 (7)
C1	0.0379 (10)	0.0518 (13)	0.0398 (11)	0.0080 (9)	0.0012 (8)	−0.0012 (9)
C8	0.0476 (11)	0.0506 (12)	0.0273 (9)	0.0040 (9)	0.0098 (8)	0.0005 (8)
C9	0.0469 (11)	0.0432 (11)	0.0328 (10)	0.0021 (9)	0.0027 (8)	−0.0006 (8)
C2	0.0496 (13)	0.0833 (18)	0.0328 (11)	0.0222 (12)	0.0030 (9)	0.0039 (11)
C3	0.0556 (14)	0.0810 (19)	0.0499 (14)	0.0238 (13)	0.0176 (11)	0.0276 (13)
C5	0.0470 (12)	0.0463 (12)	0.0428 (12)	0.0029 (9)	0.0092 (9)	0.0015 (9)
C4	0.0609 (15)	0.0533 (14)	0.0644 (16)	0.0074 (11)	0.0182 (12)	0.0193 (12)
C11	0.0466 (12)	0.0502 (13)	0.0535 (13)	−0.0035 (10)	0.0093 (10)	−0.0009 (10)
C14	0.0668 (17)	0.0531 (15)	0.0709 (19)	0.0091 (12)	−0.0193 (15)	0.0019 (14)
N6	0.090 (2)	0.103 (2)	0.079 (2)	0.0088 (17)	−0.0171 (17)	0.0133 (17)
C13	0.081 (2)	0.091 (2)	0.081 (2)	0.0105 (18)	−0.0045 (18)	−0.0079 (19)

Geometric parameters (Å, º)

S1—O1	1.4180 (15)	C10—C11	1.489 (3)
S1—O2	1.4280 (15)	C1—C2	1.375 (3)
S1—N1	1.6222 (18)	C8—C9	1.349 (3)
S1—C7	1.771 (2)	C8—H8	0.9300
N4—C10	1.329 (3)	C9—H9	0.9300
N4—C12	1.347 (3)	C2—C3	1.364 (4)
N5—N2	1.358 (2)	C2—H2	0.9300
N5—C8	1.360 (3)	C3—C4	1.375 (4)
N5—C12	1.375 (2)	C3—H3	0.9300
N1—C6	1.419 (2)	C5—C4	1.372 (3)
N1—H1	0.84 (3)	C4—H4	0.9300
F1—C1	1.342 (3)	C11—H11A	0.9600
N3—C12	1.333 (3)	C11—H11B	0.9600
N3—C7	1.350 (2)	C11—H11C	0.9600
N2—C7	1.328 (2)	C14—N6	1.135 (4)
F2—C5	1.345 (3)	C14—C13	1.439 (5)
C6—C1	1.383 (3)	C13—H13A	0.9600
C6—C5	1.385 (3)	C13—H13B	0.9600
C10—C9	1.421 (3)	C13—H13C	0.9600
O1—S1—O2	121.90 (10)	C9—C8—H8	121.9
O1—S1—N1	108.52 (9)	N5—C8—H8	121.9
O2—S1—N1	105.75 (10)	C8—C9—C10	120.52 (19)
O1—S1—C7	106.93 (9)	C8—C9—H9	119.7
O2—S1—C7	105.96 (9)	C10—C9—H9	119.7
N1—S1—C7	106.96 (9)	C3—C2—C1	119.5 (2)
C10—N4—C12	116.61 (17)	C3—C2—H2	120.2
N2—N5—C8	127.40 (16)	C1—C2—H2	120.2
N2—N5—C12	110.38 (16)	C2—C3—C4	121.0 (2)
C8—N5—C12	122.20 (17)	C2—C3—H3	119.5
C6—N1—S1	123.04 (14)	C4—C3—H3	119.5
C6—N1—H1	117.7 (17)	F2—C5—C4	119.9 (2)
S1—N1—H1	112.9 (17)	F2—C5—C6	116.79 (19)
C12—N3—C7	101.70 (16)	C4—C5—C6	123.3 (2)
N3—C12—N4	128.42 (17)	C5—C4—C3	118.0 (2)
N3—C12—N5	109.52 (17)	C5—C4—H4	121.0
N4—C12—N5	122.06 (17)	C3—C4—H4	121.0
C7—N2—N5	100.53 (15)	C10—C11—H11A	109.5
C1—C6—C5	116.13 (19)	C10—C11—H11B	109.5
C1—C6—N1	122.47 (19)	H11A—C11—H11B	109.5
C5—C6—N1	121.18 (18)	C10—C11—H11C	109.5
N4—C10—C9	122.26 (19)	H11A—C11—H11C	109.5
N4—C10—C11	118.48 (18)	H11B—C11—H11C	109.5
C9—C10—C11	119.26 (19)	N6—C14—C13	178.2 (4)
N2—C7—N3	117.86 (18)	C14—C13—H13A	109.5
N2—C7—S1	118.25 (15)	C14—C13—H13B	109.5
N3—C7—S1	123.88 (15)	H13A—C13—H13B	109.5
F1—C1—C2	119.3 (2)	C14—C13—H13C	109.5
F1—C1—C6	118.7 (2)	H13A—C13—H13C	109.5
C2—C1—C6	122.0 (2)	H13B—C13—H13C	109.5
C9—C8—N5	116.28 (18)
O1—S1—N1—C6	37.19 (19)	N1—S1—C7—N2	−87.74 (17)
O2—S1—N1—C6	169.52 (16)	O1—S1—C7—N3	−25.26 (19)
C7—S1—N1—C6	−77.85 (18)	O2—S1—C7—N3	−156.67 (17)
C7—N3—C12—N4	−179.64 (19)	N1—S1—C7—N3	90.84 (18)
C7—N3—C12—N5	0.3 (2)	C5—C6—C1—F1	178.16 (18)
C10—N4—C12—N3	−177.18 (19)	N1—C6—C1—F1	3.6 (3)
C10—N4—C12—N5	2.9 (3)	C5—C6—C1—C2	−0.9 (3)
N2—N5—C12—N3	−0.7 (2)	N1—C6—C1—C2	−175.44 (19)
C8—N5—C12—N3	178.02 (18)	N2—N5—C8—C9	178.75 (19)
N2—N5—C12—N4	179.23 (17)	C12—N5—C8—C9	0.2 (3)
C8—N5—C12—N4	−2.0 (3)	N5—C8—C9—C10	0.5 (3)
C8—N5—N2—C7	−177.91 (19)	N4—C10—C9—C8	0.4 (3)
C12—N5—N2—C7	0.8 (2)	C11—C10—C9—C8	−179.4 (2)
S1—N1—C6—C1	−77.4 (2)	F1—C1—C2—C3	−177.8 (2)
S1—N1—C6—C5	108.3 (2)	C6—C1—C2—C3	1.2 (3)
C12—N4—C10—C9	−2.1 (3)	C1—C2—C3—C4	−0.2 (4)
C12—N4—C10—C11	177.74 (19)	C1—C6—C5—F2	−179.49 (19)
N5—N2—C7—N3	−0.6 (2)	N1—C6—C5—F2	−4.8 (3)
N5—N2—C7—S1	178.06 (13)	C1—C6—C5—C4	−0.5 (3)
C12—N3—C7—N2	0.2 (2)	N1—C6—C5—C4	174.2 (2)
C12—N3—C7—S1	−178.40 (14)	F2—C5—C4—C3	−179.6 (2)
O1—S1—C7—N2	156.16 (16)	C6—C5—C4—C3	1.4 (4)
O2—S1—C7—N2	24.74 (18)	C2—C3—C4—C5	−1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4^i	0.84 (3)	2.22 (3)	3.056 (2)	178 (2)

Symmetry code: (i) x+1, y, z.