2-(2,4-Dichloro­phen­yl)-5-methyl-4-(2-nitro­phenyl­sulfon­yl)-2H-1,2,4-triazol-3(4H)-one

The title compound, C₁₅H₁₀Cl₂N₄O₅S, is a potent new herbicide. Intra­molecular C—H...O and inter­molecular C—H...O and C—H...N hydrogen bonds seem to be effective in the crystal structure. The inter­molecular hydrogen bonds link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.104
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

2-(2,4-Dichlorophenyl)-5-methyl-4-(2-nitrophenylsulfonyl)-2H-1,2,4- triazol-3(4H)-one

Crystal data

C15H10Cl2N4O5S	F(000) = 872
Mr = 429.23	Dx = 1.624 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4187 reflections
a = 8.192 (2) Å	θ = 2.3–26.2°
b = 12.648 (3) Å	µ = 0.53 mm^−1
c = 16.975 (4) Å	T = 294 K
β = 93.155 (4)°	Prism, colorless
V = 1756.1 (7) Å^3	0.28 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker 1000 CCD area-detector diffractometer	3654 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.860, Tmax = 0.900	k = −15→15
9780 measured reflections	l = −21→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.9596P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3654 reflections	Δρmax = 0.57 e Å^−3
246 parameters	Δρmin = −0.57 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0235 (13)

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	0.22952 (7)	0.52420 (4)	0.34821 (3)	0.03331 (16)
Cl1	0.07290 (8)	0.69737 (5)	0.05810 (4)	0.04933 (19)
Cl2	0.36623 (12)	0.57862 (6)	−0.20042 (4)	0.0738 (3)
O1	0.3224 (2)	0.62940 (13)	0.19429 (9)	0.0488 (4)
O2	0.1673 (2)	0.44306 (13)	0.39586 (9)	0.0429 (4)
O3	0.1656 (2)	0.62811 (13)	0.35209 (10)	0.0478 (4)
O4	0.4117 (2)	0.30611 (14)	0.33875 (12)	0.0573 (5)
O5	0.5090 (3)	0.29454 (17)	0.45946 (13)	0.0756 (7)
N1	0.1977 (2)	0.48863 (14)	0.12645 (10)	0.0360 (4)
N2	0.1259 (2)	0.39336 (14)	0.14695 (11)	0.0384 (4)
N3	0.1979 (2)	0.48491 (14)	0.25434 (10)	0.0340 (4)
N4	0.4813 (3)	0.34252 (16)	0.39789 (13)	0.0457 (5)
C1	0.1871 (3)	0.60433 (16)	0.01097 (13)	0.0333 (5)
C2	0.2298 (3)	0.62617 (18)	−0.06515 (13)	0.0372 (5)
H2	0.2051	0.6913	−0.0884	0.045*
C3	0.3095 (3)	0.54931 (19)	−0.10558 (13)	0.0401 (5)
C4	0.3443 (3)	0.45176 (18)	−0.07375 (14)	0.0414 (5)
H4	0.3925	0.3996	−0.1033	0.050*
C5	0.3061 (3)	0.43268 (17)	0.00318 (13)	0.0384 (5)
H5	0.3319	0.3676	0.0261	0.046*
C6	0.2303 (3)	0.50883 (17)	0.04647 (12)	0.0326 (5)
C7	0.2494 (3)	0.54723 (17)	0.19065 (13)	0.0363 (5)
C8	0.1257 (3)	0.39263 (17)	0.22277 (13)	0.0364 (5)
C9	0.0496 (4)	0.3066 (2)	0.26757 (15)	0.0552 (7)
H9A	0.0097	0.2526	0.2317	0.083*
H9B	−0.0396	0.3346	0.2954	0.083*
H9C	0.1296	0.2767	0.3046	0.083*
C10	0.4440 (3)	0.53342 (17)	0.36412 (12)	0.0332 (5)
C11	0.5141 (3)	0.63192 (19)	0.35598 (14)	0.0442 (6)
H11	0.4510	0.6882	0.3364	0.053*
C12	0.6786 (4)	0.6468 (2)	0.37695 (17)	0.0579 (7)
H12	0.7264	0.7126	0.3698	0.070*
C13	0.7711 (3)	0.5650 (3)	0.40821 (18)	0.0602 (8)
H13	0.8804	0.5762	0.4237	0.072*
C14	0.7034 (3)	0.4665 (2)	0.41684 (16)	0.0520 (7)
H14	0.7662	0.4112	0.4382	0.062*
C15	0.5424 (3)	0.45082 (18)	0.39359 (13)	0.0370 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0379 (3)	0.0338 (3)	0.0286 (3)	0.0031 (2)	0.0050 (2)	−0.0031 (2)
Cl1	0.0579 (4)	0.0439 (4)	0.0475 (4)	0.0103 (3)	0.0146 (3)	−0.0073 (3)
Cl2	0.1120 (7)	0.0732 (5)	0.0393 (4)	0.0233 (5)	0.0321 (4)	0.0113 (3)
O1	0.0707 (12)	0.0350 (9)	0.0406 (9)	−0.0213 (8)	0.0007 (8)	0.0011 (7)
O2	0.0460 (9)	0.0531 (10)	0.0305 (8)	−0.0033 (8)	0.0104 (7)	0.0038 (7)
O3	0.0519 (10)	0.0404 (9)	0.0510 (10)	0.0144 (8)	0.0013 (8)	−0.0100 (8)
O4	0.0690 (12)	0.0382 (10)	0.0646 (12)	−0.0008 (9)	0.0028 (10)	−0.0037 (9)
O5	0.0961 (17)	0.0647 (14)	0.0665 (14)	0.0053 (12)	0.0079 (12)	0.0332 (11)
N1	0.0527 (11)	0.0279 (9)	0.0279 (9)	−0.0107 (8)	0.0050 (8)	0.0007 (7)
N2	0.0491 (11)	0.0308 (10)	0.0355 (10)	−0.0124 (8)	0.0043 (9)	0.0014 (8)
N3	0.0449 (10)	0.0297 (9)	0.0276 (9)	−0.0070 (8)	0.0043 (8)	0.0007 (7)
N4	0.0518 (12)	0.0375 (11)	0.0488 (13)	0.0114 (9)	0.0119 (10)	0.0093 (10)
C1	0.0366 (11)	0.0302 (11)	0.0334 (11)	−0.0011 (9)	0.0050 (9)	−0.0045 (9)
C2	0.0472 (13)	0.0327 (12)	0.0320 (11)	0.0031 (10)	0.0045 (10)	0.0033 (9)
C3	0.0496 (14)	0.0426 (13)	0.0286 (11)	0.0014 (11)	0.0077 (10)	0.0018 (10)
C4	0.0509 (14)	0.0361 (12)	0.0378 (13)	0.0024 (10)	0.0084 (11)	−0.0073 (10)
C5	0.0488 (13)	0.0277 (11)	0.0388 (12)	−0.0011 (10)	0.0017 (11)	0.0025 (9)
C6	0.0385 (11)	0.0315 (11)	0.0280 (10)	−0.0064 (9)	0.0024 (9)	−0.0006 (8)
C7	0.0442 (13)	0.0327 (12)	0.0321 (11)	−0.0053 (10)	0.0034 (10)	0.0009 (9)
C8	0.0431 (13)	0.0326 (11)	0.0337 (12)	−0.0092 (10)	0.0030 (10)	0.0013 (9)
C9	0.0716 (18)	0.0494 (15)	0.0447 (14)	−0.0299 (14)	0.0041 (13)	0.0092 (12)
C10	0.0398 (12)	0.0326 (11)	0.0275 (11)	−0.0009 (9)	0.0053 (9)	−0.0037 (9)
C11	0.0533 (15)	0.0343 (12)	0.0455 (14)	−0.0040 (11)	0.0077 (11)	−0.0058 (10)
C12	0.0625 (17)	0.0542 (17)	0.0585 (17)	−0.0212 (14)	0.0152 (14)	−0.0136 (14)
C13	0.0397 (14)	0.080 (2)	0.0615 (18)	−0.0096 (14)	0.0077 (13)	−0.0117 (15)
C14	0.0423 (14)	0.0656 (18)	0.0483 (15)	0.0102 (13)	0.0043 (12)	0.0019 (13)
C15	0.0416 (12)	0.0408 (13)	0.0293 (11)	0.0025 (10)	0.0081 (10)	−0.0003 (9)

Geometric parameters (Å, º)

S1—O3	1.4177 (17)	C3—C4	1.371 (3)
S1—O2	1.4185 (16)	C4—C5	1.381 (3)
S1—N3	1.6756 (18)	C4—H4	0.9300
S1—C10	1.767 (2)	C5—C6	1.380 (3)
Cl1—C1	1.727 (2)	C5—H5	0.9300
Cl2—C3	1.740 (2)	C8—C9	1.485 (3)
O1—C7	1.199 (3)	C9—H9A	0.9600
O4—N4	1.217 (3)	C9—H9B	0.9600
O5—N4	1.219 (3)	C9—H9C	0.9600
N1—C7	1.366 (3)	C10—C11	1.382 (3)
N1—N2	1.393 (2)	C10—C15	1.395 (3)
N1—C6	1.421 (3)	C11—C12	1.388 (4)
N2—C8	1.287 (3)	C11—H11	0.9300
N3—C8	1.401 (3)	C12—C13	1.372 (4)
N3—C7	1.421 (3)	C12—H12	0.9300
N4—C15	1.462 (3)	C13—C14	1.374 (4)
C1—C2	1.385 (3)	C13—H13	0.9300
C1—C6	1.387 (3)	C14—C15	1.370 (3)
C2—C3	1.376 (3)	C14—H14	0.9300
C2—H2	0.9300
O3—S1—O2	119.93 (11)	C5—C6—N1	119.8 (2)
O3—S1—N3	106.32 (10)	C1—C6—N1	120.98 (19)
O2—S1—N3	106.62 (9)	O1—C7—N1	130.0 (2)
O3—S1—C10	107.36 (10)	O1—C7—N3	127.6 (2)
O2—S1—C10	110.24 (10)	N1—C7—N3	102.35 (17)
N3—S1—C10	105.40 (10)	N2—C8—N3	110.65 (18)
C7—N1—N2	112.75 (17)	N2—C8—C9	122.8 (2)
C7—N1—C6	126.75 (18)	N3—C8—C9	126.5 (2)
N2—N1—C6	119.87 (17)	C8—C9—H9A	109.5
C8—N2—N1	106.24 (17)	C8—C9—H9B	109.5
C8—N3—C7	107.94 (17)	H9A—C9—H9B	109.5
C8—N3—S1	130.59 (15)	C8—C9—H9C	109.5
C7—N3—S1	121.47 (15)	H9A—C9—H9C	109.5
O4—N4—O5	125.1 (2)	H9B—C9—H9C	109.5
O4—N4—C15	117.4 (2)	C11—C10—C15	118.4 (2)
O5—N4—C15	117.5 (2)	C11—C10—S1	117.35 (18)
C2—C1—C6	120.5 (2)	C15—C10—S1	123.73 (17)
C2—C1—Cl1	117.87 (17)	C10—C11—C12	120.0 (2)
C6—C1—Cl1	121.60 (17)	C10—C11—H11	120.0
C3—C2—C1	118.4 (2)	C12—C11—H11	120.0
C3—C2—H2	120.8	C13—C12—C11	120.3 (3)
C1—C2—H2	120.8	C13—C12—H12	119.9
C4—C3—C2	122.3 (2)	C11—C12—H12	119.9
C4—C3—Cl2	119.76 (18)	C12—C13—C14	120.5 (3)
C2—C3—Cl2	117.99 (18)	C12—C13—H13	119.7
C3—C4—C5	118.5 (2)	C14—C13—H13	119.7
C3—C4—H4	120.7	C15—C14—C13	119.2 (3)
C5—C4—H4	120.7	C15—C14—H14	120.4
C6—C5—C4	120.9 (2)	C13—C14—H14	120.4
C6—C5—H5	119.5	C14—C15—C10	121.5 (2)
C4—C5—H5	119.5	C14—C15—N4	116.6 (2)
C5—C6—C1	119.2 (2)	C10—C15—N4	121.8 (2)
C7—N1—N2—C8	2.4 (3)	S1—N3—C7—O1	2.4 (3)
C6—N1—N2—C8	173.9 (2)	C8—N3—C7—N1	2.3 (2)
O3—S1—N3—C8	−128.9 (2)	S1—N3—C7—N1	−178.75 (15)
O2—S1—N3—C8	0.1 (2)	N1—N2—C8—N3	−0.8 (3)
C10—S1—N3—C8	117.3 (2)	N1—N2—C8—C9	176.2 (2)
O3—S1—N3—C7	52.4 (2)	C7—N3—C8—N2	−1.0 (3)
O2—S1—N3—C7	−178.56 (17)	S1—N3—C8—N2	−179.82 (17)
C10—S1—N3—C7	−61.38 (19)	C7—N3—C8—C9	−177.8 (2)
C6—C1—C2—C3	2.7 (3)	S1—N3—C8—C9	3.4 (4)
Cl1—C1—C2—C3	−174.96 (18)	O3—S1—C10—C11	−16.8 (2)
C1—C2—C3—C4	1.5 (4)	O2—S1—C10—C11	−149.03 (17)
C1—C2—C3—Cl2	−178.72 (18)	N3—S1—C10—C11	96.28 (18)
C2—C3—C4—C5	−3.8 (4)	O3—S1—C10—C15	154.99 (18)
Cl2—C3—C4—C5	176.42 (19)	O2—S1—C10—C15	22.7 (2)
C3—C4—C5—C6	1.9 (4)	N3—S1—C10—C15	−91.96 (19)
C4—C5—C6—C1	2.2 (3)	C15—C10—C11—C12	0.0 (3)
C4—C5—C6—N1	−177.7 (2)	S1—C10—C11—C12	172.18 (19)
C2—C1—C6—C5	−4.6 (3)	C10—C11—C12—C13	−2.1 (4)
Cl1—C1—C6—C5	173.03 (17)	C11—C12—C13—C14	2.0 (4)
C2—C1—C6—N1	175.3 (2)	C12—C13—C14—C15	0.2 (4)
Cl1—C1—C6—N1	−7.0 (3)	C13—C14—C15—C10	−2.4 (4)
C7—N1—C6—C5	122.9 (3)	C13—C14—C15—N4	174.9 (2)
N2—N1—C6—C5	−47.4 (3)	C11—C10—C15—C14	2.3 (3)
C7—N1—C6—C1	−57.1 (3)	S1—C10—C15—C14	−169.35 (19)
N2—N1—C6—C1	132.7 (2)	C11—C10—C15—N4	−174.8 (2)
N2—N1—C7—O1	175.9 (2)	S1—C10—C15—N4	13.5 (3)
C6—N1—C7—O1	5.1 (4)	O4—N4—C15—C14	−127.7 (2)
N2—N1—C7—N3	−2.9 (2)	O5—N4—C15—C14	49.8 (3)
C6—N1—C7—N3	−173.7 (2)	O4—N4—C15—C10	49.6 (3)
C8—N3—C7—O1	−176.6 (2)	O5—N4—C15—C10	−132.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.93	2.51	3.439 (3)	175
C9—H9A···O3^ii	0.96	2.52	3.455 (3)	165
C9—H9C···O4	0.96	2.38	3.141 (4)	136
C11—H11···O3	0.93	2.49	2.852 (3)	104
C12—H12···N2^iii	0.93	2.61	3.539 (3)	177

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