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The title compound, C17H16N4O5S, is a new herbicide. X-ray crystal structure analysis reveals that intra- and inter­molecular C—H...O hydrogen bonds exist in the crystal structure and inter­molecular weak hydrogen bonds link the mol­ecules into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018107/bq2006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018107/bq2006Isup2.hkl
Contains datablock I

CCDC reference: 646742

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.110
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
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 2 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 0 ALERT type 5 Informative message, check

Computing details top

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.

1-(2,4-Dimethylphenyl)-3-methyl-4-(2-nitrophenylsulfonyl)- 1H-1,2,4-triazol-5(4H)-one top
Crystal data top
C17H16N4O5SZ = 2
Mr = 388.40F(000) = 404
Triclinic, P1Dx = 1.422 Mg m3
a = 7.8875 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.9125 (13) ÅCell parameters from 3037 reflections
c = 15.029 (3) Åθ = 2.8–26.4°
α = 96.040 (3)°µ = 0.22 mm1
β = 96.765 (3)°T = 294 K
γ = 100.710 (3)°Block, colourless
V = 907.4 (3) Å30.22 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3660 independent reflections
Radiation source: fine-focus sealed tube3035 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.954, Tmax = 0.966k = 99
5214 measured reflectionsl = 1815
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2272P]
where P = (Fo2 + 2Fc2)/3
3660 reflections(Δ/σ)max = 0.009
247 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
S10.21260 (6)0.63080 (5)0.91267 (3)0.04105 (14)
O10.40747 (16)0.44960 (18)0.77793 (10)0.0562 (4)
O20.07301 (17)0.70888 (17)0.93693 (9)0.0524 (3)
O30.28719 (19)0.52543 (18)0.97068 (9)0.0585 (4)
O40.0917 (2)0.8587 (2)0.76488 (12)0.0743 (5)
O50.1384 (2)1.1019 (2)0.85298 (15)0.0894 (6)
N10.14249 (19)0.3573 (2)0.68355 (11)0.0496 (4)
N20.13855 (17)0.50887 (18)0.81212 (10)0.0407 (3)
N30.03033 (19)0.3744 (2)0.68676 (12)0.0531 (4)
N40.1816 (2)0.9698 (2)0.82287 (13)0.0553 (4)
C10.1944 (2)0.2883 (2)0.60105 (13)0.0464 (4)
C20.2375 (3)0.3978 (3)0.53730 (15)0.0564 (5)
C30.2821 (3)0.3239 (3)0.45721 (16)0.0660 (6)
H30.31060.39490.41340.079*
C40.2860 (3)0.1503 (3)0.44011 (14)0.0594 (5)
C50.2438 (4)0.0477 (3)0.50524 (17)0.0756 (7)
H5A0.24660.06970.49530.091*
C60.1974 (3)0.1142 (3)0.58528 (16)0.0684 (6)
H60.16820.04200.62840.082*
C70.2341 (4)0.5882 (3)0.5532 (2)0.0941 (9)
H7A0.11940.60240.56340.141*
H7B0.26430.64150.50120.141*
H7C0.31650.64220.60510.141*
C80.3314 (4)0.0742 (4)0.35150 (17)0.0864 (8)
H8A0.23090.00450.31840.130*
H8B0.42420.01280.36320.130*
H8C0.36790.16580.31660.130*
C90.2518 (2)0.4380 (2)0.75891 (12)0.0427 (4)
C100.0303 (2)0.4644 (2)0.76333 (13)0.0450 (4)
C110.1906 (2)0.5099 (3)0.79394 (16)0.0608 (5)
H11A0.29090.44670.75350.091*
H11B0.18550.63220.79430.091*
H11C0.19880.48030.85380.091*
C120.3843 (2)0.7934 (2)0.89039 (11)0.0372 (4)
C130.5541 (2)0.7774 (2)0.91934 (12)0.0443 (4)
H130.57450.67870.94380.053*
C140.6932 (2)0.9088 (3)0.91168 (13)0.0504 (4)
H140.80660.89670.93000.061*
C150.6641 (3)1.0567 (3)0.87717 (14)0.0532 (5)
H150.75821.14360.87210.064*
C160.4958 (3)1.0777 (2)0.84987 (13)0.0512 (5)
H160.47621.17890.82790.061*
C170.3579 (2)0.9451 (2)0.85602 (11)0.0413 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0420 (2)0.0437 (2)0.0403 (2)0.01136 (18)0.00807 (17)0.01110 (17)
O10.0338 (7)0.0637 (8)0.0700 (9)0.0187 (6)0.0019 (6)0.0063 (7)
O20.0486 (7)0.0601 (8)0.0523 (7)0.0148 (6)0.0175 (6)0.0054 (6)
O30.0625 (9)0.0600 (8)0.0559 (8)0.0119 (7)0.0026 (7)0.0273 (7)
O40.0606 (10)0.0750 (11)0.0828 (11)0.0115 (8)0.0160 (8)0.0230 (9)
O50.0733 (11)0.0641 (10)0.1437 (18)0.0392 (9)0.0219 (11)0.0196 (11)
N10.0360 (8)0.0556 (9)0.0554 (9)0.0120 (7)0.0046 (7)0.0048 (7)
N20.0334 (7)0.0401 (7)0.0499 (8)0.0117 (6)0.0054 (6)0.0048 (6)
N30.0339 (8)0.0620 (10)0.0607 (10)0.0101 (7)0.0030 (7)0.0008 (8)
N40.0501 (9)0.0522 (10)0.0703 (11)0.0167 (8)0.0096 (8)0.0261 (9)
C10.0419 (10)0.0464 (10)0.0500 (10)0.0122 (8)0.0037 (8)0.0011 (8)
C20.0602 (12)0.0446 (10)0.0672 (13)0.0150 (9)0.0156 (10)0.0048 (9)
C30.0771 (15)0.0639 (13)0.0634 (13)0.0194 (11)0.0218 (11)0.0153 (11)
C40.0622 (13)0.0634 (13)0.0523 (11)0.0213 (10)0.0038 (10)0.0048 (10)
C50.114 (2)0.0469 (12)0.0701 (15)0.0316 (13)0.0144 (14)0.0014 (11)
C60.1023 (18)0.0499 (12)0.0587 (13)0.0250 (12)0.0151 (12)0.0110 (10)
C70.127 (2)0.0456 (13)0.121 (2)0.0236 (14)0.052 (2)0.0147 (14)
C80.097 (2)0.0983 (19)0.0629 (15)0.0305 (16)0.0117 (14)0.0151 (14)
C90.0376 (9)0.0398 (9)0.0522 (10)0.0123 (7)0.0073 (8)0.0031 (7)
C100.0324 (9)0.0477 (10)0.0551 (11)0.0082 (7)0.0062 (7)0.0074 (8)
C110.0334 (10)0.0765 (14)0.0736 (14)0.0137 (9)0.0116 (9)0.0051 (11)
C120.0400 (9)0.0377 (8)0.0344 (8)0.0100 (7)0.0060 (7)0.0025 (6)
C130.0440 (10)0.0463 (9)0.0434 (9)0.0147 (8)0.0025 (7)0.0031 (7)
C140.0385 (10)0.0584 (11)0.0510 (11)0.0097 (8)0.0029 (8)0.0043 (9)
C150.0492 (11)0.0497 (11)0.0561 (11)0.0004 (8)0.0118 (9)0.0020 (9)
C160.0594 (12)0.0412 (10)0.0553 (11)0.0109 (8)0.0143 (9)0.0091 (8)
C170.0437 (9)0.0421 (9)0.0409 (9)0.0136 (7)0.0086 (7)0.0068 (7)
Geometric parameters (Å, º) top
S1—O31.4198 (13)C5—H5A0.9300
S1—O21.4236 (13)C6—H60.9300
S1—N21.6827 (15)C7—H7A0.9600
S1—C121.7752 (17)C7—H7B0.9600
O1—C91.212 (2)C7—H7C0.9600
O4—N41.223 (2)C8—H8A0.9600
O5—N41.218 (2)C8—H8B0.9600
N1—C91.359 (2)C8—H8C0.9600
N1—N31.400 (2)C10—C111.487 (2)
N1—C11.437 (2)C11—H11A0.9600
N2—C101.406 (2)C11—H11B0.9600
N2—C91.418 (2)C11—H11C0.9600
N3—C101.288 (2)C12—C131.392 (2)
N4—C171.476 (2)C12—C171.396 (2)
C1—C61.378 (3)C13—C141.388 (3)
C1—C21.388 (3)C13—H130.9300
C2—C31.394 (3)C14—C151.375 (3)
C2—C71.506 (3)C14—H140.9300
C3—C41.378 (3)C15—C161.387 (3)
C3—H30.9300C15—H150.9300
C4—C51.368 (3)C16—C171.383 (3)
C4—C81.513 (3)C16—H160.9300
C5—C61.379 (3)
O3—S1—O2120.32 (9)H7A—C7—H7C109.5
O3—S1—N2107.57 (8)H7B—C7—H7C109.5
O2—S1—N2106.24 (8)C4—C8—H8A109.5
O3—S1—C12107.59 (8)C4—C8—H8B109.5
O2—S1—C12109.41 (8)H8A—C8—H8B109.5
N2—S1—C12104.64 (7)C4—C8—H8C109.5
C9—N1—N3112.77 (15)H8A—C8—H8C109.5
C9—N1—C1125.77 (15)H8B—C8—H8C109.5
N3—N1—C1120.52 (15)O1—C9—N1129.98 (17)
C10—N2—C9107.73 (14)O1—C9—N2127.22 (17)
C10—N2—S1130.31 (12)N1—C9—N2102.81 (14)
C9—N2—S1121.89 (12)N3—C10—N2110.72 (15)
C10—N3—N1105.97 (15)N3—C10—C11123.10 (17)
O5—N4—O4124.72 (19)N2—C10—C11126.17 (17)
O5—N4—C17117.69 (18)C10—C11—H11A109.5
O4—N4—C17117.54 (16)C10—C11—H11B109.5
C6—C1—C2120.86 (18)H11A—C11—H11B109.5
C6—C1—N1119.82 (18)C10—C11—H11C109.5
C2—C1—N1119.30 (16)H11A—C11—H11C109.5
C1—C2—C3117.21 (18)H11B—C11—H11C109.5
C1—C2—C7121.6 (2)C13—C12—C17118.55 (16)
C3—C2—C7121.2 (2)C13—C12—S1117.42 (13)
C4—C3—C2122.9 (2)C17—C12—S1123.54 (13)
C4—C3—H3118.6C14—C13—C12120.05 (17)
C2—C3—H3118.6C14—C13—H13120.0
C5—C4—C3117.8 (2)C12—C13—H13120.0
C5—C4—C8120.9 (2)C15—C14—C13120.37 (17)
C3—C4—C8121.3 (2)C15—C14—H14119.8
C4—C5—C6121.5 (2)C13—C14—H14119.8
C4—C5—H5A119.2C14—C15—C16120.71 (18)
C6—C5—H5A119.2C14—C15—H15119.6
C1—C6—C5119.7 (2)C16—C15—H15119.6
C1—C6—H6120.2C17—C16—C15118.70 (18)
C5—C6—H6120.2C17—C16—H16120.6
C2—C7—H7A109.5C15—C16—H16120.6
C2—C7—H7B109.5C16—C17—C12121.58 (16)
H7A—C7—H7B109.5C16—C17—N4116.93 (16)
C2—C7—H7C109.5C12—C17—N4121.48 (16)
O3—S1—N2—C10121.23 (16)S1—N2—C9—O12.3 (3)
O2—S1—N2—C108.84 (18)C10—N2—C9—N10.18 (18)
C12—S1—N2—C10124.55 (16)S1—N2—C9—N1177.49 (12)
O3—S1—N2—C962.14 (15)N1—N3—C10—N20.0 (2)
O2—S1—N2—C9167.79 (13)N1—N3—C10—C11179.10 (18)
C12—S1—N2—C952.09 (15)C9—N2—C10—N30.1 (2)
C9—N1—N3—C100.2 (2)S1—N2—C10—N3177.10 (13)
C1—N1—N3—C10169.70 (17)C9—N2—C10—C11179.20 (18)
C9—N1—C1—C697.2 (2)S1—N2—C10—C113.8 (3)
N3—N1—C1—C694.7 (2)O3—S1—C12—C139.02 (16)
C9—N1—C1—C284.2 (2)O2—S1—C12—C13141.34 (13)
N3—N1—C1—C283.9 (2)N2—S1—C12—C13105.18 (13)
C6—C1—C2—C30.4 (3)O3—S1—C12—C17162.80 (14)
N1—C1—C2—C3178.17 (18)O2—S1—C12—C1730.49 (17)
C6—C1—C2—C7179.7 (2)N2—S1—C12—C1782.99 (15)
N1—C1—C2—C71.1 (3)C17—C12—C13—C141.6 (3)
C1—C2—C3—C40.5 (3)S1—C12—C13—C14173.82 (13)
C7—C2—C3—C4179.7 (2)C12—C13—C14—C151.3 (3)
C2—C3—C4—C50.0 (4)C13—C14—C15—C160.3 (3)
C2—C3—C4—C8178.7 (2)C14—C15—C16—C171.5 (3)
C3—C4—C5—C60.6 (4)C15—C16—C17—C121.2 (3)
C8—C4—C5—C6178.1 (2)C15—C16—C17—N4177.62 (17)
C2—C1—C6—C50.1 (4)C13—C12—C17—C160.3 (3)
N1—C1—C6—C5178.7 (2)S1—C12—C17—C16172.08 (14)
C4—C5—C6—C10.6 (4)C13—C12—C17—N4179.11 (16)
N3—N1—C9—O1179.53 (19)S1—C12—C17—N49.2 (2)
C1—N1—C9—O110.6 (3)O5—N4—C17—C1653.4 (3)
N3—N1—C9—N20.2 (2)O4—N4—C17—C16124.17 (19)
C1—N1—C9—N2169.10 (16)O5—N4—C17—C12127.8 (2)
C10—N2—C9—O1179.57 (18)O4—N4—C17—C1254.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O1i0.962.453.093 (6)124
C13—H13···O30.932.462.855 (2)105
C13—H13···O3ii0.932.493.391 (6)163
C16—H16···O1iii0.932.473.401 (4)176
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x, y1, z.
 

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