The title compound, C
17H
16N
4O
5S, 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
CCDC reference: 646742
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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)-
1
H-1,2,4-triazol-5(4
H)-one
top
Crystal data top
C17H16N4O5S | Z = 2 |
Mr = 388.40 | F(000) = 404 |
Triclinic, P1 | Dx = 1.422 Mg m−3 |
a = 7.8875 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9125 (13) Å | Cell parameters from 3037 reflections |
c = 15.029 (3) Å | θ = 2.8–26.4° |
α = 96.040 (3)° | µ = 0.22 mm−1 |
β = 96.765 (3)° | T = 294 K |
γ = 100.710 (3)° | Block, colourless |
V = 907.4 (3) Å3 | 0.22 × 0.20 × 0.16 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3660 independent reflections |
Radiation source: fine-focus sealed tube | 3035 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.954, Tmax = 0.966 | k = −9→9 |
5214 measured reflections | l = −18→15 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
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 | Uiso*/Ueq | |
S1 | 0.21260 (6) | 0.63080 (5) | 0.91267 (3) | 0.04105 (14) | |
O1 | 0.40747 (16) | 0.44960 (18) | 0.77793 (10) | 0.0562 (4) | |
O2 | 0.07301 (17) | 0.70888 (17) | 0.93693 (9) | 0.0524 (3) | |
O3 | 0.28719 (19) | 0.52543 (18) | 0.97068 (9) | 0.0585 (4) | |
O4 | 0.0917 (2) | 0.8587 (2) | 0.76488 (12) | 0.0743 (5) | |
O5 | 0.1384 (2) | 1.1019 (2) | 0.85298 (15) | 0.0894 (6) | |
N1 | 0.14249 (19) | 0.3573 (2) | 0.68355 (11) | 0.0496 (4) | |
N2 | 0.13855 (17) | 0.50887 (18) | 0.81212 (10) | 0.0407 (3) | |
N3 | −0.03033 (19) | 0.3744 (2) | 0.68676 (12) | 0.0531 (4) | |
N4 | 0.1816 (2) | 0.9698 (2) | 0.82287 (13) | 0.0553 (4) | |
C1 | 0.1944 (2) | 0.2883 (2) | 0.60105 (13) | 0.0464 (4) | |
C2 | 0.2375 (3) | 0.3978 (3) | 0.53730 (15) | 0.0564 (5) | |
C3 | 0.2821 (3) | 0.3239 (3) | 0.45721 (16) | 0.0660 (6) | |
H3 | 0.3106 | 0.3949 | 0.4134 | 0.079* | |
C4 | 0.2860 (3) | 0.1503 (3) | 0.44011 (14) | 0.0594 (5) | |
C5 | 0.2438 (4) | 0.0477 (3) | 0.50524 (17) | 0.0756 (7) | |
H5A | 0.2466 | −0.0697 | 0.4953 | 0.091* | |
C6 | 0.1974 (3) | 0.1142 (3) | 0.58528 (16) | 0.0684 (6) | |
H6 | 0.1682 | 0.0420 | 0.6284 | 0.082* | |
C7 | 0.2341 (4) | 0.5882 (3) | 0.5532 (2) | 0.0941 (9) | |
H7A | 0.1194 | 0.6024 | 0.5634 | 0.141* | |
H7B | 0.2643 | 0.6415 | 0.5012 | 0.141* | |
H7C | 0.3165 | 0.6422 | 0.6051 | 0.141* | |
C8 | 0.3314 (4) | 0.0742 (4) | 0.35150 (17) | 0.0864 (8) | |
H8A | 0.2309 | −0.0045 | 0.3184 | 0.130* | |
H8B | 0.4242 | 0.0128 | 0.3632 | 0.130* | |
H8C | 0.3679 | 0.1658 | 0.3166 | 0.130* | |
C9 | 0.2518 (2) | 0.4380 (2) | 0.75891 (12) | 0.0427 (4) | |
C10 | −0.0303 (2) | 0.4644 (2) | 0.76333 (13) | 0.0450 (4) | |
C11 | −0.1906 (2) | 0.5099 (3) | 0.79394 (16) | 0.0608 (5) | |
H11A | −0.2909 | 0.4467 | 0.7535 | 0.091* | |
H11B | −0.1855 | 0.6322 | 0.7943 | 0.091* | |
H11C | −0.1988 | 0.4803 | 0.8538 | 0.091* | |
C12 | 0.3843 (2) | 0.7934 (2) | 0.89039 (11) | 0.0372 (4) | |
C13 | 0.5541 (2) | 0.7774 (2) | 0.91934 (12) | 0.0443 (4) | |
H13 | 0.5745 | 0.6787 | 0.9438 | 0.053* | |
C14 | 0.6932 (2) | 0.9088 (3) | 0.91168 (13) | 0.0504 (4) | |
H14 | 0.8066 | 0.8967 | 0.9300 | 0.061* | |
C15 | 0.6641 (3) | 1.0567 (3) | 0.87717 (14) | 0.0532 (5) | |
H15 | 0.7582 | 1.1436 | 0.8721 | 0.064* | |
C16 | 0.4958 (3) | 1.0777 (2) | 0.84987 (13) | 0.0512 (5) | |
H16 | 0.4762 | 1.1789 | 0.8279 | 0.061* | |
C17 | 0.3579 (2) | 0.9451 (2) | 0.85602 (11) | 0.0413 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0420 (2) | 0.0437 (2) | 0.0403 (2) | 0.01136 (18) | 0.00807 (17) | 0.01110 (17) |
O1 | 0.0338 (7) | 0.0637 (8) | 0.0700 (9) | 0.0187 (6) | 0.0019 (6) | −0.0063 (7) |
O2 | 0.0486 (7) | 0.0601 (8) | 0.0523 (7) | 0.0148 (6) | 0.0175 (6) | 0.0054 (6) |
O3 | 0.0625 (9) | 0.0600 (8) | 0.0559 (8) | 0.0119 (7) | 0.0026 (7) | 0.0273 (7) |
O4 | 0.0606 (10) | 0.0750 (11) | 0.0828 (11) | 0.0115 (8) | −0.0160 (8) | 0.0230 (9) |
O5 | 0.0733 (11) | 0.0641 (10) | 0.1437 (18) | 0.0392 (9) | 0.0219 (11) | 0.0196 (11) |
N1 | 0.0360 (8) | 0.0556 (9) | 0.0554 (9) | 0.0120 (7) | 0.0046 (7) | −0.0048 (7) |
N2 | 0.0334 (7) | 0.0401 (7) | 0.0499 (8) | 0.0117 (6) | 0.0054 (6) | 0.0048 (6) |
N3 | 0.0339 (8) | 0.0620 (10) | 0.0607 (10) | 0.0101 (7) | 0.0030 (7) | −0.0008 (8) |
N4 | 0.0501 (9) | 0.0522 (10) | 0.0703 (11) | 0.0167 (8) | 0.0096 (8) | 0.0261 (9) |
C1 | 0.0419 (10) | 0.0464 (10) | 0.0500 (10) | 0.0122 (8) | 0.0037 (8) | −0.0011 (8) |
C2 | 0.0602 (12) | 0.0446 (10) | 0.0672 (13) | 0.0150 (9) | 0.0156 (10) | 0.0048 (9) |
C3 | 0.0771 (15) | 0.0639 (13) | 0.0634 (13) | 0.0194 (11) | 0.0218 (11) | 0.0153 (11) |
C4 | 0.0622 (13) | 0.0634 (13) | 0.0523 (11) | 0.0213 (10) | 0.0038 (10) | −0.0048 (10) |
C5 | 0.114 (2) | 0.0469 (12) | 0.0701 (15) | 0.0316 (13) | 0.0144 (14) | −0.0014 (11) |
C6 | 0.1023 (18) | 0.0499 (12) | 0.0587 (13) | 0.0250 (12) | 0.0151 (12) | 0.0110 (10) |
C7 | 0.127 (2) | 0.0456 (13) | 0.121 (2) | 0.0236 (14) | 0.052 (2) | 0.0147 (14) |
C8 | 0.097 (2) | 0.0983 (19) | 0.0629 (15) | 0.0305 (16) | 0.0117 (14) | −0.0151 (14) |
C9 | 0.0376 (9) | 0.0398 (9) | 0.0522 (10) | 0.0123 (7) | 0.0073 (8) | 0.0031 (7) |
C10 | 0.0324 (9) | 0.0477 (10) | 0.0551 (11) | 0.0082 (7) | 0.0062 (7) | 0.0074 (8) |
C11 | 0.0334 (10) | 0.0765 (14) | 0.0736 (14) | 0.0137 (9) | 0.0116 (9) | 0.0051 (11) |
C12 | 0.0400 (9) | 0.0377 (8) | 0.0344 (8) | 0.0100 (7) | 0.0060 (7) | 0.0025 (6) |
C13 | 0.0440 (10) | 0.0463 (9) | 0.0434 (9) | 0.0147 (8) | 0.0025 (7) | 0.0031 (7) |
C14 | 0.0385 (10) | 0.0584 (11) | 0.0510 (11) | 0.0097 (8) | 0.0029 (8) | −0.0043 (9) |
C15 | 0.0492 (11) | 0.0497 (11) | 0.0561 (11) | 0.0004 (8) | 0.0118 (9) | −0.0020 (9) |
C16 | 0.0594 (12) | 0.0412 (10) | 0.0553 (11) | 0.0109 (8) | 0.0143 (9) | 0.0091 (8) |
C17 | 0.0437 (9) | 0.0421 (9) | 0.0409 (9) | 0.0136 (7) | 0.0086 (7) | 0.0068 (7) |
Geometric parameters (Å, º) top
S1—O3 | 1.4198 (13) | C5—H5A | 0.9300 |
S1—O2 | 1.4236 (13) | C6—H6 | 0.9300 |
S1—N2 | 1.6827 (15) | C7—H7A | 0.9600 |
S1—C12 | 1.7752 (17) | C7—H7B | 0.9600 |
O1—C9 | 1.212 (2) | C7—H7C | 0.9600 |
O4—N4 | 1.223 (2) | C8—H8A | 0.9600 |
O5—N4 | 1.218 (2) | C8—H8B | 0.9600 |
N1—C9 | 1.359 (2) | C8—H8C | 0.9600 |
N1—N3 | 1.400 (2) | C10—C11 | 1.487 (2) |
N1—C1 | 1.437 (2) | C11—H11A | 0.9600 |
N2—C10 | 1.406 (2) | C11—H11B | 0.9600 |
N2—C9 | 1.418 (2) | C11—H11C | 0.9600 |
N3—C10 | 1.288 (2) | C12—C13 | 1.392 (2) |
N4—C17 | 1.476 (2) | C12—C17 | 1.396 (2) |
C1—C6 | 1.378 (3) | C13—C14 | 1.388 (3) |
C1—C2 | 1.388 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.394 (3) | C14—C15 | 1.375 (3) |
C2—C7 | 1.506 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.378 (3) | C15—C16 | 1.387 (3) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.368 (3) | C16—C17 | 1.383 (3) |
C4—C8 | 1.513 (3) | C16—H16 | 0.9300 |
C5—C6 | 1.379 (3) | | |
| | | |
O3—S1—O2 | 120.32 (9) | H7A—C7—H7C | 109.5 |
O3—S1—N2 | 107.57 (8) | H7B—C7—H7C | 109.5 |
O2—S1—N2 | 106.24 (8) | C4—C8—H8A | 109.5 |
O3—S1—C12 | 107.59 (8) | C4—C8—H8B | 109.5 |
O2—S1—C12 | 109.41 (8) | H8A—C8—H8B | 109.5 |
N2—S1—C12 | 104.64 (7) | C4—C8—H8C | 109.5 |
C9—N1—N3 | 112.77 (15) | H8A—C8—H8C | 109.5 |
C9—N1—C1 | 125.77 (15) | H8B—C8—H8C | 109.5 |
N3—N1—C1 | 120.52 (15) | O1—C9—N1 | 129.98 (17) |
C10—N2—C9 | 107.73 (14) | O1—C9—N2 | 127.22 (17) |
C10—N2—S1 | 130.31 (12) | N1—C9—N2 | 102.81 (14) |
C9—N2—S1 | 121.89 (12) | N3—C10—N2 | 110.72 (15) |
C10—N3—N1 | 105.97 (15) | N3—C10—C11 | 123.10 (17) |
O5—N4—O4 | 124.72 (19) | N2—C10—C11 | 126.17 (17) |
O5—N4—C17 | 117.69 (18) | C10—C11—H11A | 109.5 |
O4—N4—C17 | 117.54 (16) | C10—C11—H11B | 109.5 |
C6—C1—C2 | 120.86 (18) | H11A—C11—H11B | 109.5 |
C6—C1—N1 | 119.82 (18) | C10—C11—H11C | 109.5 |
C2—C1—N1 | 119.30 (16) | H11A—C11—H11C | 109.5 |
C1—C2—C3 | 117.21 (18) | H11B—C11—H11C | 109.5 |
C1—C2—C7 | 121.6 (2) | C13—C12—C17 | 118.55 (16) |
C3—C2—C7 | 121.2 (2) | C13—C12—S1 | 117.42 (13) |
C4—C3—C2 | 122.9 (2) | C17—C12—S1 | 123.54 (13) |
C4—C3—H3 | 118.6 | C14—C13—C12 | 120.05 (17) |
C2—C3—H3 | 118.6 | C14—C13—H13 | 120.0 |
C5—C4—C3 | 117.8 (2) | C12—C13—H13 | 120.0 |
C5—C4—C8 | 120.9 (2) | C15—C14—C13 | 120.37 (17) |
C3—C4—C8 | 121.3 (2) | C15—C14—H14 | 119.8 |
C4—C5—C6 | 121.5 (2) | C13—C14—H14 | 119.8 |
C4—C5—H5A | 119.2 | C14—C15—C16 | 120.71 (18) |
C6—C5—H5A | 119.2 | C14—C15—H15 | 119.6 |
C1—C6—C5 | 119.7 (2) | C16—C15—H15 | 119.6 |
C1—C6—H6 | 120.2 | C17—C16—C15 | 118.70 (18) |
C5—C6—H6 | 120.2 | C17—C16—H16 | 120.6 |
C2—C7—H7A | 109.5 | C15—C16—H16 | 120.6 |
C2—C7—H7B | 109.5 | C16—C17—C12 | 121.58 (16) |
H7A—C7—H7B | 109.5 | C16—C17—N4 | 116.93 (16) |
C2—C7—H7C | 109.5 | C12—C17—N4 | 121.48 (16) |
| | | |
O3—S1—N2—C10 | 121.23 (16) | S1—N2—C9—O1 | 2.3 (3) |
O2—S1—N2—C10 | −8.84 (18) | C10—N2—C9—N1 | −0.18 (18) |
C12—S1—N2—C10 | −124.55 (16) | S1—N2—C9—N1 | −177.49 (12) |
O3—S1—N2—C9 | −62.14 (15) | N1—N3—C10—N2 | 0.0 (2) |
O2—S1—N2—C9 | 167.79 (13) | N1—N3—C10—C11 | −179.10 (18) |
C12—S1—N2—C9 | 52.09 (15) | C9—N2—C10—N3 | 0.1 (2) |
C9—N1—N3—C10 | −0.2 (2) | S1—N2—C10—N3 | 177.10 (13) |
C1—N1—N3—C10 | −169.70 (17) | C9—N2—C10—C11 | 179.20 (18) |
C9—N1—C1—C6 | 97.2 (2) | S1—N2—C10—C11 | −3.8 (3) |
N3—N1—C1—C6 | −94.7 (2) | O3—S1—C12—C13 | 9.02 (16) |
C9—N1—C1—C2 | −84.2 (2) | O2—S1—C12—C13 | 141.34 (13) |
N3—N1—C1—C2 | 83.9 (2) | N2—S1—C12—C13 | −105.18 (13) |
C6—C1—C2—C3 | 0.4 (3) | O3—S1—C12—C17 | −162.80 (14) |
N1—C1—C2—C3 | −178.17 (18) | O2—S1—C12—C17 | −30.49 (17) |
C6—C1—C2—C7 | 179.7 (2) | N2—S1—C12—C17 | 82.99 (15) |
N1—C1—C2—C7 | 1.1 (3) | C17—C12—C13—C14 | −1.6 (3) |
C1—C2—C3—C4 | −0.5 (3) | S1—C12—C13—C14 | −173.82 (13) |
C7—C2—C3—C4 | −179.7 (2) | C12—C13—C14—C15 | 1.3 (3) |
C2—C3—C4—C5 | 0.0 (4) | C13—C14—C15—C16 | 0.3 (3) |
C2—C3—C4—C8 | 178.7 (2) | C14—C15—C16—C17 | −1.5 (3) |
C3—C4—C5—C6 | 0.6 (4) | C15—C16—C17—C12 | 1.2 (3) |
C8—C4—C5—C6 | −178.1 (2) | C15—C16—C17—N4 | −177.62 (17) |
C2—C1—C6—C5 | 0.1 (4) | C13—C12—C17—C16 | 0.3 (3) |
N1—C1—C6—C5 | 178.7 (2) | S1—C12—C17—C16 | 172.08 (14) |
C4—C5—C6—C1 | −0.6 (4) | C13—C12—C17—N4 | 179.11 (16) |
N3—N1—C9—O1 | −179.53 (19) | S1—C12—C17—N4 | −9.2 (2) |
C1—N1—C9—O1 | −10.6 (3) | O5—N4—C17—C16 | −53.4 (3) |
N3—N1—C9—N2 | 0.2 (2) | O4—N4—C17—C16 | 124.17 (19) |
C1—N1—C9—N2 | 169.10 (16) | O5—N4—C17—C12 | 127.8 (2) |
C10—N2—C9—O1 | 179.57 (18) | O4—N4—C17—C12 | −54.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O1i | 0.96 | 2.45 | 3.093 (6) | 124 |
C13—H13···O3 | 0.93 | 2.46 | 2.855 (2) | 105 |
C13—H13···O3ii | 0.93 | 2.49 | 3.391 (6) | 163 |
C16—H16···O1iii | 0.93 | 2.47 | 3.401 (4) | 176 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x, y−1, z. |